Chemical context   {#sec1}
==================

Ebastine, or 4-(benzhydr­yloxy)-1-\[4-(4-*tert*-butyl­phen­yl)-4-oxo­but­yl\]piperidine, is a non-sedating second generation H~1~ receptor antagonist, which is effective in the treatment of both allergic rhinitis, whether seasonal or perennial, and chronic idiopathic urticaria (Wiseman & Faulds, 1996[@bb15]; Van Cauwenberge *et al.*, 2004[@bb14]). The structure of ebastine has been the subject of two recent reports (Cheng *et al.*, 2005[@bb2]: Sharma *et al.*, 2015[@bb10]). Herein, we report the mol­ecular and supra­molecular structure of the 1:1 salt ebastinium 3,5-di­nitro­benzoate (I)[](#scheme1){ref-type="chem"}, formed in the reaction between ebastine and 3,5-di­nitro­benzoic acid.

Structural commentary   {#sec2}
=======================

The title compound (I)[](#scheme1){ref-type="chem"}, consists of an N-protonated ebastinium cation and a 3,5-di­nitro­benzoate anion (Fig. 1[▸](#fig1){ref-type="fig"}), which are linked within the selected asymmetric unit a by a fairly short and nearly linear N---H⋯O hydrogen bond (Fig. 1[▸](#fig1){ref-type="fig"}, Table 1[▸](#table1){ref-type="table"}). The disubstituted aryl ring in the cation is disordered over two sets of atomic sites having occupancies 0.706 (4) for the major ring orientation, labelled C161--C166, and 0.294 (4) for the minor orientation, labeled C171--C176: the dihedral angle between these two ring planes is 41.2 (5)° (Fig. 1[▸](#fig1){ref-type="fig"}). The piperidine ring adopts an almost perfect chair conformation, with a ring-puckering angle, calculated for the atom sequence (N1,C2,C3,C4,C5,C6) of θ = 0.0 (3)°, identical within experimental uncertainty to the idealized value for a perfect chair form of θ = 0.0° (Boeyens, 1978[@bb1]). However, although the non-H substituent at atom N1 in the ring occupies an equatorial site, as expected, the bulky Ph~2~CHO substituent at atom C4 unexpectedly occupies an axial site. This observation is the more surprising since in ebastine itself, both non-H substit­uents on the piperidine ring occupy equatorial sites (Cheng *et al.*, 2005[@bb2]: Sharma *et al.*, 2015[@bb10]). The 3,5-di­nitro­benzoate anion in compound (I)[](#scheme1){ref-type="chem"} is nearly planar: the dihedral angles between the aryl ring and the substituents at atoms C21, C23 and C25 are 1.4 (2), 4.2 (2) and 10.7 (2)°, respectively: only the O atoms of the 5-nitro group are significantly displaced from the mean plane of the anion as a whole, 0.219 (2) Å for atom O25 and 0.187 (2) Å for atom O26: the r.m.s. deviation from the mean plane for the entire anion is only 0.082 Å.

Supra­molecular features   {#sec3}
==========================

In addition to the N---H⋯O hydrogen bond within the selected asymmetric unit, already noted (*cf*. Fig. 1[▸](#fig1){ref-type="fig"} and Table 1[▸](#table1){ref-type="table"}), there are two C---H⋯O hydrogen bonds in the crystal of compound (I)[](#scheme1){ref-type="chem"}, which link the components into complex sheets, whose formation can, however, be readily analysed in terms of two simple, one-dimensional sub-structures (Ferguson *et al.*, 1998*a* [@bb3],*b* [@bb4]; Gregson *et al.*, 2000[@bb5]). In the simpler of the two sub-structures, cations related by translation are linked by a single C---H⋯O hydrogen bond to form a *C*(6) chain running parallel to the \[100\] direction (Fig. 2[▸](#fig2){ref-type="fig"}, Table 1[▸](#table1){ref-type="table"}). The second sub-structure involves the cations and the anions, and a combination of the N---H⋯O hydrogen bond and a second C---H⋯O hydrogen bond links ions related by a *c*-glide plane into a (11) chain, running parallel to the \[20\] direction, in which cations and anions alternate (Fig. 3[▸](#fig3){ref-type="fig"}, Table 1[▸](#table1){ref-type="table"}). The combination of these two chain motifs generates a sheet lying parallel to (010) in the domain 0.5 \< *y* \< 1.0, and a second such sheet, related to the first by inversion, lies in the domain 0.0 \< *y* \< 0.5, but there are no direction-specific inter­actions between adjacent sheets. It is inter­esting to note that none of the hydrogen bonds in compound (I)[](#scheme1){ref-type="chem"} involves the Ph~2~CHO substituent, so that direction-specific inter­actions cannot be held responsible for the location of this substituent at an axial site on the piperidine ring.

Database survey   {#sec4}
=================

The mol­ecular structure of neutral ebastine (Cheng *et al.*, 2005[@bb2]; Sharma *et al.*, 2015[@bb10]) differs from that of the ebastinium cation in compound (I)[](#scheme1){ref-type="chem"} in two significant respects. Firstly, there is no disorder in the neutral compound as opposed to the orientation disorder of the disubstituted aryl ring in (I)[](#scheme1){ref-type="chem"} and secondly, both of the non-H substituents on the piperidine ring occupy equatorial sites in the neutral compound as opposed to the presence of one axial and one equatorial substituent in (I)[](#scheme1){ref-type="chem"}. Neither of the two reports on the structure of ebastine gave any description of the supra­molecular assembly: one (Cheng *et al.*, 2005[@bb2]) noted the presence of hydrogen bonds, but the second (Sharma *et al.*, 2015[@bb10]) did not record these. Accordingly, we have now examined the supra­molecular assembly of ebastine using the most recently reported atomic coordinates (Sharma *et al.*, 2015[@bb10]): a combination of one C---H⋯N hydrogen bond and one C---H⋯O hydrogen bond links the mol­ecules into sheets lying parallel to (100) and containing (20) and (48) rings, both centrosymmetric, arranges in chess board fashion (Fig. 4[▸](#fig4){ref-type="fig"}). Structures have also been reported recently for some structurally related compounds with pharmacological activity, including the picrate salt of the anti­cholinergic drug propiverine, 4-(2,2-diphenyl-2-prop­oxy­acet­oxy)-1-meth­ylpiperidin-1-ium picrate (Jasinski *et al.*, 2009[@bb6]), and the anti-spasmodic drug pargeverine, *N*,*N*-dimeth­yl-\[2-(2,2-diphen­yl)-2-prop-2-yn­yloxy)acet­oxy\]ethyl­amine and its picrate and (2*R*,3*R*)-(hydrogentartrate) salts (Shaibah *et al.*, 2017[@bb9]).

Synthesis and crystallization   {#sec5}
===============================

A sample of ebastine was a gift from RL Fine Chem, Pvt. Ltd., Bengaluru, India. For the synthesis of compound (I)[](#scheme1){ref-type="chem"}, ebastine (100 mg, 0.20 mmol) and 3,5-di­nitro­benzoic acid (45 mg, 0.20 mmol) were dissolved in hot methanol and held at 333 K for 30 min, with magnetic stirring throughout. The resulting solution was then allowed to cool slowly to room temperature, giving colourless block-like crystals (m.p. 424--428 K).

Refinement   {#sec6}
============

Crystal data, data collection and structure refinement details are summarized in Table 2[▸](#table2){ref-type="table"}. Three low-angle reflections (021), (002) and (012), which had been attenuated by the beam stop, were omitted from the refinements. It was apparent from an early stage in the refinement that the disubstituted aryl ring was disordered over two sets of atomic sights having unequal occupancies, and corresponding to different orientations of this ring relative to its substituents. For the minor orientation, the bonded distances and the 1,3-non-bonded distances were restrained to be the same as the corresponding distances in the major orientation, subject to s.u.s of 0.01 and 0.02 Å, respect­ively: in addition, the anisotropic displacement parameters for corresponding pairs of atomic sites were constrained to be equal. All H atoms, other than those in the minor disorder components, were located in difference-Fourier maps. The C-bound H atoms were all treated as riding atoms in geometrically idealized positions: C---H 0.93 Å (aromatic), 0.96 Å (CH~3~), 0.97 Å (CH~2~) or 0.98 Å (aliphatic C---H), with *U* ~iso~(H) = 1.5*U* ~eq~(C-meth­yl) and 1.2*U* ~eq~(C) for other H atoms. The methyl groups were permitted to rotate but not to tilt. For the H atom bonded to the N atom, the atomic coordinates were refined with *U* ~iso~(H) = 1.2*U* ~eq~(N), giving an N---H distance of 0.99 (3) Å. Subject to these conditions, the occupancies of the two disordered components refined to 0.706 (4) and 0.294 (4). In the final analysis of variance there was a large value, 15.256, of *K* = \[mean(*F* ~o~ ^2^)/mean(*F* ~c~ ^2^)\] for the group of 867 very weak reflections having *F* ~c~/*F* ~c~(max) in the range 0.000 \< *F* ~c~/*F* ~c~(max) \< 0.005.

Supplementary Material
======================

Crystal structure: contains datablock(s) global, I. DOI: [10.1107/S205698901701324X/su5391sup1.cif](https://doi.org/10.1107/S205698901701324X/su5391sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S205698901701324X/su5391Isup2.hkl](https://doi.org/10.1107/S205698901701324X/su5391Isup2.hkl)

###### 

Click here for additional data file.

Supporting information file. DOI: [10.1107/S205698901701324X/su5391Isup3.cml](https://doi.org/10.1107/S205698901701324X/su5391Isup3.cml)

CCDC reference: [1574718](http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1574718)

Additional supporting information: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?su5391&file=su5391sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?su5391sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?su5391&checkcif=yes)

The authors thank the DST--PURSE Lab. (Mangalore University) for the diffractometer and other facilities. MAES thanks the University of Mysore for research facilities and BKS thanks the UGC for the award of a Rajiv Gandhi National Fellowship.

Crystal data {#d1e134}
============

  ---------------------------------------- ----------------------------------------
  C~32~H~40~NO~2~^+^·C~7~H~3~N~2~O~6~^−^   *F*(000) = 1448
  *M~r~* = 681.76                          *D*~x~ = 1.292 Mg m^−3^
  Monoclinic, *P*2~1~/*c*                  Mo *K*α radiation, λ = 0.71073 Å
  *a* = 5.9168 (3) Å                       Cell parameters from 10431 reflections
  *b* = 28.3733 (12) Å                     θ = 2.4--31.2°
  *c* = 21.0782 (11) Å                     µ = 0.09 mm^−1^
  β = 97.836 (5)°                          *T* = 293 K
  *V* = 3505.6 (3) Å^3^                    Block, colourless
  *Z* = 4                                  0.23 × 0.21 × 0.18 mm
  ---------------------------------------- ----------------------------------------

Data collection {#d1e275}
===============

  ------------------------------------------------------------------- --------------------------------------
  Rigaku Saturn724 diffractometer                                     4388 reflections with *I* \> 2σ(*I*)
  Radiation source: fine focus sealed tube                            *R*~int~ = 0.061
  φ and ω scans                                                       θ~max~ = 26.6°, θ~min~ = 2.4°
  Absorption correction: multi-scan (SADABS; Krause *et al.*, 2015)   *h* = −7→7
  *T*~min~ = 0.956, *T*~max~ = 0.984                                  *k* = −35→35
  40112 measured reflections                                          *l* = −26→25
  7331 independent reflections                                        
  ------------------------------------------------------------------- --------------------------------------

Refinement {#d1e391}
==========

  ------------------------------------- -------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.065   Hydrogen site location: mixed
  *wR*(*F*^2^) = 0.179                  H atoms treated by a mixture of independent and constrained refinement
  *S* = 1.05                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0661*P*)^2^ + 1.0412*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  7331 reflections                      (Δ/σ)~max~ = 0.001
  470 parameters                        Δρ~max~ = 0.20 e Å^−3^
  22 restraints                         Δρ~min~ = −0.25 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

Special details {#d1e547}
===============

  -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
  -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#d1e566}
==================================================================================================

  ------ ------------- -------------- -------------- -------------------- ------------
         *x*           *y*            *z*            *U*~iso~\*/*U*~eq~   Occ. (\<1)
  N1     0.3135 (4)    0.72898 (6)    0.37455 (11)   0.0510 (5)           
  H1     0.374 (4)     0.7192 (8)     0.3349 (12)    0.061\*              
  C2     0.4460 (4)    0.77114 (8)    0.40021 (11)   0.0479 (6)           
  H2B    0.6062        0.7629         0.4097         0.057\*              
  H2A    0.3938        0.7811         0.4398         0.057\*              
  C3     0.4185 (4)    0.81101 (8)    0.35285 (11)   0.0457 (6)           
  H3A    0.4826        0.8018         0.3147         0.055\*              
  H3B    0.5027        0.8382         0.3713         0.055\*              
  C4     0.1701 (4)    0.82448 (8)    0.33437 (11)   0.0457 (6)           
  H4     0.1579        0.8488         0.3011         0.055\*              
  C5     0.0386 (4)    0.78137 (9)    0.30906 (12)   0.0553 (7)           
  H5A    −0.1219       0.7892         0.2994         0.066\*              
  H5B    0.0916        0.7713         0.2697         0.066\*              
  C6     0.0676 (4)    0.74172 (9)    0.35682 (13)   0.0575 (7)           
  H6A    0.0043        0.7510         0.3950         0.069\*              
  H6B    −0.0160       0.7144         0.3388         0.069\*              
  O4     0.0623 (3)    0.84055 (5)    0.38735 (7)    0.0484 (4)           
  C41    0.1566 (4)    0.88157 (8)    0.41962 (11)   0.0460 (6)           
  H41    0.3107        0.8739         0.4403         0.055\*              
  C141   0.0098 (4)    0.89282 (8)    0.47183 (11)   0.0453 (6)           
  C142   −0.1660 (4)   0.86412 (9)    0.48464 (11)   0.0511 (6)           
  H142   −0.1975       0.8367         0.4610         0.061\*              
  C143   −0.2974 (5)   0.87546 (10)   0.53237 (12)   0.0613 (7)           
  H143   −0.4159       0.8557         0.5403         0.074\*              
  C144   −0.2527 (6)   0.91565 (10)   0.56772 (13)   0.0686 (8)           
  H144   −0.3422       0.9236         0.5991         0.082\*              
  C145   −0.0755 (6)   0.94408 (10)   0.55665 (15)   0.0798 (10)          
  H145   −0.0426       0.9711         0.5812         0.096\*              
  C146   0.0550 (6)    0.93287 (9)    0.50904 (14)   0.0719 (8)           
  H146   0.1749        0.9525         0.5019         0.086\*              
  C151   0.1735 (4)    0.92244 (8)    0.37464 (11)   0.0469 (6)           
  C152   0.3761 (5)    0.94689 (9)    0.37596 (14)   0.0612 (7)           
  H152   0.5016        0.9380         0.4050         0.073\*              
  C153   0.3962 (6)    0.98416 (10)   0.33510 (18)   0.0770 (9)           
  H153   0.5338        1.0003         0.3368         0.092\*              
  C154   0.2134 (7)    0.99730 (11)   0.29230 (17)   0.0808 (10)          
  H154   0.2264        1.0222         0.2644         0.097\*              
  C155   0.0086 (6)    0.97356 (11)   0.29040 (15)   0.0754 (9)           
  H155   −0.1161       0.9827         0.2613         0.091\*              
  C156   −0.0118 (5)   0.93637 (9)    0.33152 (13)   0.0603 (7)           
  H156   −0.1504       0.9207         0.3302         0.072\*              
  C11    0.3376 (6)    0.68892 (10)   0.42095 (17)   0.0865 (11)          
  H11A   0.2213        0.6656         0.4071         0.104\*              
  H11B   0.3101        0.7005         0.4625         0.104\*              
  C12    0.5687 (5)    0.66527 (9)    0.42801 (16)   0.0724 (9)           
  H12A   0.6523        0.6664         0.4737         0.087\*              
  H12B   0.6523        0.6776         0.4014         0.087\*              
  C13    0.5462 (5)    0.61430 (10)   0.41343 (17)   0.0833 (10)          
  H13A   0.4697        0.6108         0.3700         0.100\*              
  H13B   0.4481        0.6005         0.4417         0.100\*              
  C14    0.7637 (6)    0.58644 (10)   0.41954 (15)   0.0709 (8)           
  O14    0.9451 (4)    0.60527 (8)    0.43408 (16)   0.1170 (10)          
  C161   0.7488 (5)    0.53513 (9)    0.40590 (14)   0.0659 (8)           0.706 (4)
  C162   0.5497 (7)    0.51590 (14)   0.3727 (3)     0.0902 (17)          0.706 (4)
  H162   0.4245        0.5351         0.3599         0.108\*              0.706 (4)
  C163   0.5386 (7)    0.46828 (14)   0.3589 (3)     0.0907 (18)          0.706 (4)
  H163   0.4054        0.4561         0.3364         0.109\*              0.706 (4)
  C164   0.7209 (5)    0.43792 (9)    0.37782 (13)   0.0587 (7)           0.706 (4)
  C165   0.9157 (9)    0.45915 (18)   0.4048 (5)     0.103 (4)            0.706 (4)
  H165   1.0458        0.4407         0.4147         0.124\*              0.706 (4)
  C166   0.9308 (9)    0.50664 (17)   0.4185 (4)     0.099 (3)            0.706 (4)
  H166   1.0697        0.5192         0.4367         0.119\*              0.706 (4)
  C171   0.7488 (5)    0.53513 (9)    0.40590 (14)   0.0659 (8)           0.294 (4)
  C172   0.5662 (15)   0.5073 (3)     0.4211 (5)     0.0902 (17)          0.294 (4)
  H172   0.4497        0.5216         0.4396         0.108\*              0.294 (4)
  C173   0.5554 (15)   0.4594 (3)     0.4093 (5)     0.0907 (18)          0.294 (4)
  H173   0.4382        0.4415         0.4223         0.109\*              0.294 (4)
  C174   0.7209 (5)    0.43792 (9)    0.37782 (13)   0.0587 (7)           0.294 (4)
  C175   0.9160 (17)   0.4626 (4)     0.3793 (15)    0.103 (4)            0.294 (4)
  H175   1.0483        0.4468         0.3726         0.124\*              0.294 (4)
  C176   0.9267 (18)   0.5104 (4)     0.3905 (12)    0.099 (3)            0.294 (4)
  H176   1.0625        0.5262         0.3872         0.119\*              0.294 (4)
  C181   0.7009 (5)    0.38550 (9)    0.36135 (13)   0.0591 (7)           
  C182   0.6091 (6)    0.35909 (12)   0.41549 (16)   0.0925 (11)          
  H18A   0.5908        0.3264         0.4044         0.139\*              
  H18B   0.4643        0.3721         0.4220         0.139\*              
  H18C   0.7145        0.3622         0.4541         0.139\*              
  C183   0.9278 (5)    0.36413 (11)   0.35081 (18)   0.0903 (11)          
  H18D   1.0326        0.3661         0.3897         0.135\*              
  H18E   0.9883        0.3811         0.3175         0.135\*              
  H18F   0.9059        0.3317         0.3386         0.135\*              
  C184   0.5349 (5)    0.37825 (11)   0.29982 (14)   0.0753 (8)           
  H18G   0.5895        0.3949         0.2653         0.113\*              
  H18H   0.3872        0.3900         0.3058         0.113\*              
  H18I   0.5240        0.3453         0.2898         0.113\*              
  C21    0.7522 (4)    0.69940 (8)    0.19856 (11)   0.0431 (5)           
  C22    0.8763 (4)    0.66079 (8)    0.22368 (11)   0.0458 (6)           
  H22    0.8338        0.6448         0.2587         0.055\*              
  C23    1.0631 (4)    0.64614 (8)    0.19644 (12)   0.0486 (6)           
  C24    1.1306 (4)    0.66812 (9)    0.14419 (12)   0.0525 (6)           
  H24    1.2571        0.6579         0.1263         0.063\*              
  C25    1.0032 (4)    0.70587 (9)    0.11964 (11)   0.0505 (6)           
  C26    0.8156 (4)    0.72192 (8)    0.14567 (11)   0.0493 (6)           
  H26    0.7327        0.7476         0.1278         0.059\*              
  C27    0.5535 (4)    0.71822 (9)    0.23013 (13)   0.0504 (6)           
  O21    0.4514 (3)    0.75292 (7)    0.20644 (9)    0.0689 (5)           
  O22    0.5158 (3)    0.69618 (6)    0.27979 (9)    0.0649 (5)           
  N23    1.1983 (4)    0.60593 (8)    0.22480 (13)   0.0672 (6)           
  O23    1.1460 (4)    0.58894 (8)    0.27369 (12)   0.0920 (7)           
  O24    1.3561 (4)    0.59235 (8)    0.19822 (12)   0.1010 (8)           
  N25    1.0724 (5)    0.72964 (9)    0.06325 (12)   0.0700 (7)           
  O25    1.2546 (4)    0.71894 (9)    0.04679 (11)   0.0974 (8)           
  O26    0.9409 (5)    0.75808 (9)    0.03539 (11)   0.1034 (8)           
  ------ ------------- -------------- -------------- -------------------- ------------

Atomic displacement parameters (Å^2^) {#d1e1894}
=====================================

  ------ ------------- ------------- ------------- -------------- -------------- --------------
         *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  N1     0.0585 (13)   0.0405 (10)   0.0606 (13)   0.0002 (9)     0.0321 (11)    −0.0031 (10)
  C2     0.0490 (14)   0.0496 (13)   0.0474 (14)   0.0035 (11)    0.0147 (11)    −0.0072 (11)
  C3     0.0470 (14)   0.0421 (12)   0.0508 (14)   −0.0017 (10)   0.0168 (11)    −0.0075 (11)
  C4     0.0480 (14)   0.0472 (13)   0.0444 (13)   0.0039 (11)    0.0150 (11)    −0.0043 (11)
  C5     0.0430 (14)   0.0664 (16)   0.0576 (16)   0.0005 (12)    0.0108 (12)    −0.0223 (13)
  C6     0.0514 (16)   0.0545 (15)   0.0722 (18)   −0.0128 (12)   0.0285 (14)    −0.0229 (14)
  O4     0.0520 (10)   0.0442 (9)    0.0527 (10)   0.0011 (7)     0.0203 (8)     −0.0131 (7)
  C41    0.0446 (13)   0.0415 (12)   0.0521 (14)   0.0040 (10)    0.0076 (11)    −0.0054 (11)
  C141   0.0513 (14)   0.0397 (12)   0.0453 (13)   0.0080 (11)    0.0082 (11)    −0.0019 (10)
  C142   0.0510 (15)   0.0579 (15)   0.0441 (14)   0.0011 (12)    0.0058 (12)    −0.0045 (12)
  C143   0.0581 (17)   0.0772 (19)   0.0501 (15)   0.0059 (14)    0.0130 (13)    0.0065 (14)
  C144   0.088 (2)     0.0690 (18)   0.0540 (17)   0.0236 (17)    0.0277 (16)    0.0054 (15)
  C145   0.122 (3)     0.0537 (17)   0.070 (2)     0.0072 (18)    0.040 (2)      −0.0174 (15)
  C146   0.100 (2)     0.0518 (16)   0.0696 (19)   −0.0091 (15)   0.0334 (18)    −0.0129 (14)
  C151   0.0498 (14)   0.0416 (12)   0.0521 (14)   0.0045 (11)    0.0171 (12)    −0.0075 (11)
  C152   0.0595 (17)   0.0526 (15)   0.0755 (19)   0.0007 (13)    0.0234 (15)    −0.0081 (14)
  C153   0.079 (2)     0.0557 (17)   0.106 (3)     0.0001 (16)    0.047 (2)      −0.0010 (18)
  C154   0.117 (3)     0.0544 (17)   0.083 (2)     0.0105 (19)    0.056 (2)      0.0096 (16)
  C155   0.092 (2)     0.0709 (19)   0.0646 (19)   0.0251 (18)    0.0133 (17)    0.0088 (16)
  C156   0.0614 (17)   0.0567 (16)   0.0640 (17)   0.0072 (13)    0.0131 (14)    0.0013 (14)
  C11    0.109 (3)     0.0547 (16)   0.110 (3)     0.0158 (17)    0.069 (2)      0.0279 (17)
  C12    0.089 (2)     0.0500 (15)   0.086 (2)     0.0124 (15)    0.0381 (18)    0.0181 (15)
  C13    0.087 (2)     0.0635 (18)   0.095 (2)     0.0207 (16)    −0.0026 (19)   −0.0269 (17)
  C14    0.073 (2)     0.0543 (16)   0.083 (2)     0.0038 (15)    0.0015 (17)    −0.0062 (15)
  O14    0.0782 (17)   0.0650 (14)   0.200 (3)     −0.0039 (12)   −0.0078 (17)   −0.0152 (16)
  C161   0.0586 (17)   0.0523 (15)   0.085 (2)     0.0033 (14)    0.0038 (15)    −0.0064 (14)
  C162   0.071 (3)     0.063 (2)     0.125 (5)     0.028 (2)      −0.031 (3)     −0.023 (3)
  C163   0.062 (2)     0.065 (2)     0.136 (5)     0.0107 (19)    −0.023 (3)     −0.029 (3)
  C164   0.0531 (16)   0.0537 (15)   0.0714 (18)   0.0057 (13)    0.0157 (14)    −0.0063 (13)
  C165   0.064 (2)     0.056 (2)     0.181 (11)    0.0166 (17)    −0.013 (3)     −0.014 (4)
  C166   0.061 (2)     0.057 (2)     0.170 (10)    0.0066 (17)    −0.017 (3)     −0.011 (3)
  C171   0.0586 (17)   0.0523 (15)   0.085 (2)     0.0033 (14)    0.0038 (15)    −0.0064 (14)
  C172   0.071 (3)     0.063 (2)     0.125 (5)     0.028 (2)      −0.031 (3)     −0.023 (3)
  C173   0.062 (2)     0.065 (2)     0.136 (5)     0.0107 (19)    −0.023 (3)     −0.029 (3)
  C174   0.0531 (16)   0.0537 (15)   0.0714 (18)   0.0057 (13)    0.0157 (14)    −0.0063 (13)
  C175   0.064 (2)     0.056 (2)     0.181 (11)    0.0166 (17)    −0.013 (3)     −0.014 (4)
  C176   0.061 (2)     0.057 (2)     0.170 (10)    0.0066 (17)    −0.017 (3)     −0.011 (3)
  C181   0.0610 (17)   0.0529 (15)   0.0659 (17)   0.0014 (13)    0.0175 (14)    0.0020 (13)
  C182   0.121 (3)     0.087 (2)     0.073 (2)     −0.007 (2)     0.028 (2)      0.0090 (18)
  C183   0.079 (2)     0.069 (2)     0.124 (3)     0.0164 (17)    0.019 (2)      −0.014 (2)
  C184   0.085 (2)     0.0685 (18)   0.074 (2)     −0.0021 (16)   0.0180 (17)    −0.0076 (16)
  C21    0.0455 (13)   0.0423 (12)   0.0432 (13)   −0.0045 (10)   0.0127 (11)    −0.0105 (10)
  C22    0.0518 (14)   0.0467 (13)   0.0406 (13)   −0.0047 (11)   0.0124 (11)    −0.0067 (10)
  C23    0.0479 (14)   0.0481 (13)   0.0496 (14)   0.0050 (11)    0.0062 (12)    −0.0117 (11)
  C24    0.0476 (14)   0.0601 (15)   0.0527 (15)   −0.0056 (12)   0.0173 (12)    −0.0186 (13)
  C25    0.0535 (15)   0.0581 (15)   0.0428 (14)   −0.0097 (12)   0.0169 (12)    −0.0076 (12)
  C26    0.0536 (15)   0.0480 (13)   0.0472 (14)   −0.0034 (11)   0.0106 (12)    −0.0072 (11)
  C27    0.0486 (15)   0.0505 (14)   0.0548 (16)   −0.0031 (12)   0.0166 (12)    −0.0165 (13)
  O21    0.0677 (13)   0.0620 (12)   0.0798 (13)   0.0171 (10)    0.0207 (10)    −0.0063 (10)
  O22    0.0747 (13)   0.0646 (11)   0.0634 (12)   0.0063 (9)     0.0386 (10)    −0.0071 (10)
  N23    0.0668 (16)   0.0624 (15)   0.0715 (16)   0.0143 (12)    0.0064 (14)    −0.0117 (13)
  O23    0.1038 (18)   0.0849 (15)   0.0873 (16)   0.0259 (13)    0.0133 (14)    0.0247 (13)
  O24    0.0920 (17)   0.1013 (17)   0.1138 (19)   0.0466 (14)    0.0293 (15)    −0.0112 (15)
  N25    0.0849 (19)   0.0748 (17)   0.0557 (15)   −0.0129 (14)   0.0292 (15)    −0.0015 (13)
  O25    0.0960 (18)   0.127 (2)     0.0806 (16)   −0.0088 (15)   0.0543 (14)    −0.0002 (14)
  O26    0.132 (2)     0.1008 (18)   0.0844 (17)   0.0167 (16)    0.0413 (16)    0.0340 (15)
  ------ ------------- ------------- ------------- -------------- -------------- --------------

Geometric parameters (Å, º) {#d1e2923}
===========================

  --------------------------- -------------- --------------------------- ------------
  N1---C2                     1.491 (3)      C13---H13A                  0.9700
  N1---C11                    1.493 (3)      C13---H13B                  0.9700
  N1---C6                     1.496 (3)      C14---O14                   1.201 (3)
  N1---H1                     0.99 (3)       C14---C161                  1.484 (4)
  C2---C3                     1.503 (3)      C161---C166                 1.344 (5)
  C2---H2B                    0.9700         C161---C162                 1.397 (5)
  C2---H2A                    0.9700         C162---C163                 1.382 (5)
  C3---C4                     1.517 (3)      C162---H162                 0.9300
  C3---H3A                    0.9700         C163---C164                 1.396 (4)
  C3---H3B                    0.9700         C163---H163                 0.9300
  C4---O4                     1.434 (3)      C164---C165                 1.355 (6)
  C4---C5                     1.507 (3)      C164---C181                 1.528 (4)
  C4---H4                     0.9800         C165---C166                 1.378 (5)
  C5---C6                     1.504 (4)      C165---H165                 0.9300
  C5---H5A                    0.9700         C166---H166                 0.9300
  C5---H5B                    0.9700         C172---C173                 1.381 (8)
  C6---H6A                    0.9700         C172---H172                 0.9300
  C6---H6B                    0.9700         C173---H173                 0.9300
  O4---C41                    1.423 (3)      C175---C176                 1.376 (8)
  C41---C151                  1.510 (3)      C175---H175                 0.9300
  C41---C141                  1.526 (3)      C176---H176                 0.9300
  C41---H41                   0.9800         C181---C183                 1.517 (4)
  C141---C142                 1.377 (3)      C181---C182                 1.526 (4)
  C141---C146                 1.386 (3)      C181---C184                 1.530 (4)
  C142---C143                 1.390 (3)      C182---H18A                 0.9600
  C142---H142                 0.9300         C182---H18B                 0.9600
  C143---C144                 1.368 (4)      C182---H18C                 0.9600
  C143---H143                 0.9300         C183---H18D                 0.9600
  C144---C145                 1.368 (4)      C183---H18E                 0.9600
  C144---H144                 0.9300         C183---H18F                 0.9600
  C145---C146                 1.384 (4)      C184---H18G                 0.9600
  C145---H145                 0.9300         C184---H18H                 0.9600
  C146---H146                 0.9300         C184---H18I                 0.9600
  C151---C152                 1.382 (3)      C21---C26                   1.380 (3)
  C151---C156                 1.383 (4)      C21---C22                   1.383 (3)
  C152---C153                 1.379 (4)      C21---C27                   1.524 (3)
  C152---H152                 0.9300         C22---C23                   1.378 (3)
  C153---C154                 1.363 (5)      C22---H22                   0.9300
  C153---H153                 0.9300         C23---C24                   1.371 (3)
  C154---C155                 1.382 (5)      C23---N23                   1.473 (3)
  C154---H154                 0.9300         C24---C25                   1.370 (3)
  C155---C156                 1.381 (4)      C24---H24                   0.9300
  C155---H155                 0.9300         C25---C26                   1.381 (3)
  C156---H156                 0.9300         C25---N25                   1.472 (3)
  C11---C12                   1.512 (4)      C26---H26                   0.9300
  C11---H11A                  0.9700         C27---O21                   1.226 (3)
  C11---H11B                  0.9700         C27---O22                   1.265 (3)
  C12---C13                   1.481 (4)      N23---O24                   1.215 (3)
  C12---H12A                  1.0216         N23---O23                   1.215 (3)
  C12---H12B                  0.8703         N25---O26                   1.215 (3)
  C13---C14                   1.501 (4)      N25---O25                   1.215 (3)
                                                                         
  C2---N1---C11               112.0 (2)      C11---C12---H12A            113.2
  C2---N1---C6                110.00 (18)    C13---C12---H12B            107.6
  C11---N1---C6               110.5 (2)      C11---C12---H12B            110.1
  C2---N1---H1                107.3 (14)     H12A---C12---H12B           110.5
  C11---N1---H1               109.0 (14)     C12---C13---C14             116.4 (3)
  C6---N1---H1                107.9 (15)     C12---C13---H13A            108.2
  N1---C2---C3                111.04 (19)    C14---C13---H13A            108.2
  N1---C2---H2B               109.4          C12---C13---H13B            108.2
  C3---C2---H2B               109.4          C14---C13---H13B            108.2
  N1---C2---H2A               109.4          H13A---C13---H13B           107.3
  C3---C2---H2A               109.4          O14---C14---C161            120.9 (3)
  H2B---C2---H2A              108.0          O14---C14---C13             120.9 (3)
  C2---C3---C4                111.94 (19)    C161---C14---C13            118.2 (3)
  C2---C3---H3A               109.2          C166---C161---C162          117.5 (3)
  C4---C3---H3A               109.2          C166---C161---C14           121.8 (3)
  C2---C3---H3B               109.2          C162---C161---C14           120.3 (3)
  C4---C3---H3B               109.2          C163---C162---C161          120.0 (4)
  H3A---C3---H3B              107.9          C163---C162---H162          120.0
  O4---C4---C5                105.72 (18)    C161---C162---H162          120.0
  O4---C4---C3                113.48 (19)    C162---C163---C164          122.1 (4)
  C5---C4---C3                108.75 (19)    C162---C163---H163          119.0
  O4---C4---H4                109.6          C164---C163---H163          119.0
  C5---C4---H4                109.6          C165---C164---C163          115.2 (3)
  C3---C4---H4                109.6          C165---C164---C181          124.3 (3)
  C6---C5---C4                111.3 (2)      C163---C164---C181          120.2 (3)
  C6---C5---H5A               109.4          C164---C165---C166          123.3 (5)
  C4---C5---H5A               109.4          C164---C165---H165          118.3
  C6---C5---H5B               109.4          C166---C165---H165          118.3
  C4---C5---H5B               109.4          C161---C166---C165          121.3 (5)
  H5A---C5---H5B              108.0          C161---C166---H166          119.3
  N1---C6---C5                111.49 (19)    C165---C166---H166          119.3
  N1---C6---H6A               109.3          C173---C172---H172          119.0
  C5---C6---H6A               109.3          C172---C173---H173          120.1
  N1---C6---H6B               109.3          C176---C175---H175          118.8
  C5---C6---H6B               109.3          C175---C176---H176          118.7
  H6A---C6---H6B              108.0          C183---C181---C182          109.0 (3)
  C41---O4---C4               116.44 (17)    C183---C181---C164          112.3 (2)
  O4---C41---C151             112.52 (19)    C182---C181---C164          109.4 (2)
  O4---C41---C141             106.93 (18)    C183---C181---C184          107.5 (2)
  C151---C41---C141           112.66 (18)    C182---C181---C184          108.4 (2)
  O4---C41---H41              108.2          C164---C181---C184          110.1 (2)
  C151---C41---H41            108.2          C181---C182---H18A          109.5
  C141---C41---H41            108.2          C181---C182---H18B          109.5
  C142---C141---C146          117.8 (2)      H18A---C182---H18B          109.5
  C142---C141---C41           122.5 (2)      C181---C182---H18C          109.5
  C146---C141---C41           119.7 (2)      H18A---C182---H18C          109.5
  C141---C142---C143          121.1 (2)      H18B---C182---H18C          109.5
  C141---C142---H142          119.4          C181---C183---H18D          109.5
  C143---C142---H142          119.4          C181---C183---H18E          109.5
  C144---C143---C142          120.1 (3)      H18D---C183---H18E          109.5
  C144---C143---H143          120.0          C181---C183---H18F          109.5
  C142---C143---H143          120.0          H18D---C183---H18F          109.5
  C145---C144---C143          119.7 (3)      H18E---C183---H18F          109.5
  C145---C144---H144          120.2          C181---C184---H18G          109.5
  C143---C144---H144          120.2          C181---C184---H18H          109.5
  C144---C145---C146          120.3 (3)      H18G---C184---H18H          109.5
  C144---C145---H145          119.9          C181---C184---H18I          109.5
  C146---C145---H145          119.9          H18G---C184---H18I          109.5
  C145---C146---C141          121.0 (3)      H18H---C184---H18I          109.5
  C145---C146---H146          119.5          C26---C21---C22             119.2 (2)
  C141---C146---H146          119.5          C26---C21---C27             120.1 (2)
  C152---C151---C156          118.5 (2)      C22---C21---C27             120.7 (2)
  C152---C151---C41           120.3 (2)      C23---C22---C21             119.6 (2)
  C156---C151---C41           121.2 (2)      C23---C22---H22             120.2
  C153---C152---C151          121.4 (3)      C21---C22---H22             120.2
  C153---C152---H152          119.3          C24---C23---C22             122.4 (2)
  C151---C152---H152          119.3          C24---C23---N23             118.5 (2)
  C154---C153---C152          119.7 (3)      C22---C23---N23             119.2 (2)
  C154---C153---H153          120.2          C25---C24---C23             117.0 (2)
  C152---C153---H153          120.2          C25---C24---H24             121.5
  C153---C154---C155          120.0 (3)      C23---C24---H24             121.5
  C153---C154---H154          120.0          C24---C25---C26             122.6 (2)
  C155---C154---H154          120.0          C24---C25---N25             117.6 (2)
  C156---C155---C154          120.4 (3)      C26---C25---N25             119.8 (2)
  C156---C155---H155          119.8          C21---C26---C25             119.3 (2)
  C154---C155---H155          119.8          C21---C26---H26             120.3
  C155---C156---C151          120.1 (3)      C25---C26---H26             120.3
  C155---C156---H156          120.0          O21---C27---O22             127.0 (2)
  C151---C156---H156          120.0          O21---C27---C21             118.1 (2)
  N1---C11---C12              114.0 (2)      O22---C27---C21             115.0 (2)
  N1---C11---H11A             108.8          O24---N23---O23             124.5 (3)
  C12---C11---H11A            108.8          O24---N23---C23             117.9 (3)
  N1---C11---H11B             108.8          O23---N23---C23             117.7 (2)
  C12---C11---H11B            108.8          O26---N25---O25             124.2 (3)
  H11A---C11---H11B           107.7          O26---N25---C25             117.6 (3)
  C13---C12---C11             111.0 (3)      O25---N25---C25             118.1 (3)
  C13---C12---H12A            104.2                                      
                                                                         
  C11---N1---C2---C3          −179.77 (19)   O14---C14---C161---C166     10.3 (6)
  C6---N1---C2---C3           −56.5 (2)      C13---C14---C161---C166     −170.9 (5)
  N1---C2---C3---C4           57.2 (2)       O14---C14---C161---C162     −162.5 (4)
  C2---C3---C4---O4           61.4 (2)       C13---C14---C161---C162     16.4 (5)
  C2---C3---C4---C5           −55.9 (2)      C166---C161---C162---C163   5.6 (7)
  O4---C4---C5---C6           −66.3 (2)      C14---C161---C162---C163    178.6 (4)
  C3---C4---C5---C6           55.8 (3)       C161---C162---C163---C164   0.8 (7)
  C2---N1---C6---C5           57.0 (2)       C162---C163---C164---C165   −6.2 (8)
  C11---N1---C6---C5          −178.8 (2)     C162---C163---C164---C181   −179.9 (4)
  C4---C5---C6---N1           −57.7 (3)      C163---C164---C165---C166   5.7 (11)
  C5---C4---O4---C41          −179.83 (19)   C181---C164---C165---C166   179.0 (6)
  C3---C4---O4---C41          61.1 (3)       C162---C161---C166---C165   −6.3 (10)
  C4---O4---C41---C151        53.7 (3)       C14---C161---C166---C165    −179.2 (6)
  C4---O4---C41---C141        177.88 (18)    C164---C165---C166---C161   0.5 (13)
  O4---C41---C141---C142      4.6 (3)        C165---C164---C181---C183   −24.9 (6)
  C151---C41---C141---C142    128.7 (2)      C163---C164---C181---C183   148.2 (4)
  O4---C41---C141---C146      −176.5 (2)     C165---C164---C181---C182   96.3 (6)
  C151---C41---C141---C146    −52.4 (3)      C163---C164---C181---C182   −90.6 (4)
  C146---C141---C142---C143   1.4 (4)        C165---C164---C181---C184   −144.6 (6)
  C41---C141---C142---C143    −179.7 (2)     C163---C164---C181---C184   28.4 (4)
  C141---C142---C143---C144   −0.2 (4)       C26---C21---C22---C23       1.4 (3)
  C142---C143---C144---C145   −1.2 (4)       C27---C21---C22---C23       −176.3 (2)
  C143---C144---C145---C146   1.4 (5)        C21---C22---C23---C24       −0.9 (4)
  C144---C145---C146---C141   −0.1 (5)       C21---C22---C23---N23       178.1 (2)
  C142---C141---C146---C145   −1.3 (4)       C22---C23---C24---C25       0.0 (4)
  C41---C141---C146---C145    179.8 (3)      N23---C23---C24---C25       −179.0 (2)
  O4---C41---C151---C152      −129.7 (2)     C23---C24---C25---C26       0.4 (4)
  C141---C41---C151---C152    109.3 (2)      C23---C24---C25---N25       −179.6 (2)
  O4---C41---C151---C156      50.5 (3)       C22---C21---C26---C25       −1.0 (3)
  C141---C41---C151---C156    −70.5 (3)      C27---C21---C26---C25       176.7 (2)
  C156---C151---C152---C153   −0.6 (4)       C24---C25---C26---C21       0.1 (4)
  C41---C151---C152---C153    179.6 (2)      N25---C25---C26---C21       −180.0 (2)
  C151---C152---C153---C154   −0.2 (4)       C26---C21---C27---O21       1.3 (3)
  C152---C153---C154---C155   0.6 (5)        C22---C21---C27---O21       179.0 (2)
  C153---C154---C155---C156   −0.3 (5)       C26---C21---C27---O22       −177.2 (2)
  C154---C155---C156---C151   −0.5 (4)       C22---C21---C27---O22       0.5 (3)
  C152---C151---C156---C155   0.9 (4)        C24---C23---N23---O24       −4.2 (4)
  C41---C151---C156---C155    −179.3 (2)     C22---C23---N23---O24       176.8 (2)
  C2---N1---C11---C12         −72.4 (3)      C24---C23---N23---O23       174.9 (2)
  C6---N1---C11---C12         164.5 (3)      C22---C23---N23---O23       −4.1 (4)
  N1---C11---C12---C13        −122.9 (3)     C24---C25---N25---O26       168.7 (3)
  C11---C12---C13---C14       −179.2 (3)     C26---C25---N25---O26       −11.3 (4)
  C12---C13---C14---O14       −1.7 (5)       C24---C25---N25---O25       −9.9 (4)
  C12---C13---C14---C161      179.5 (3)      C26---C25---N25---O25       170.2 (2)
  --------------------------- -------------- --------------------------- ------------

Hydrogen-bond geometry (Å, º) {#d1e4692}
=============================

  ------------------------ ---------- ---------- ----------- ---------------
  *D*---H···*A*            *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  N1---H1···O22            0.99 (3)   1.66 (2)   2.634 (3)   167 (2)
  C2---H2*A*···O25^i^      0.97       2.50       3.444 (3)   163
  C11---H11*A*···O14^ii^   0.97       2.49       3.358 (4)   150
  ------------------------ ---------- ---------- ----------- ---------------

Symmetry codes: (i) *x*−1, −*y*+3/2, *z*+1/2; (ii) *x*−1, *y*, *z*.

![The mol­ecular structure of the ionic components of compound (I)[](#scheme1){ref-type="chem"}, showing the atom-labelling scheme, the N---H⋯O hydrogen bond within the selected asymmetric unit, and the orientational disorder of the disubstituted aryl ring (the major component is drawn with full lines and the minor component with broken lines). Displacement ellipsoids are drawn at the 30% probability level and, for clarity, a few of the atom labels have been omitted.](e-73-01513-fig1){#fig1}

![Part of the crystal structure of compound (I)[](#scheme1){ref-type="chem"}, showing a hydrogen-bonded *C*(6) chain of cations running parallel to \[100\]. For clarity, the anions, the minor disorder component of the cation, and the H atoms bonded to carrier atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (\*) or a hash (\#) are at the symmetry positions (−1 + *x*, *y*, *z*) and (1 + *x*, *y*, *z*) respectively.](e-73-01513-fig2){#fig2}

![Part of the crystal structure of compound (I)[](#scheme1){ref-type="chem"}, showing a hydrogen-bonded (11) chain running parallel to \[20\]. For clarity, the minor disorder component of the cation, and the H atoms bonded to C atoms not involved in the motif shown have been omitted.](e-73-01513-fig3){#fig3}

![Part of the crystal structure of ebastine showing the formation of a hydrogen-bonded sheet of (20) and (48) rings. The original atomic coordinates (Sharma *et al.*, 2015[@bb10]) have been used and, for the sake of clarity, the H atoms not involved in the motifs shown have been omitted.](e-73-01513-fig4){#fig4}

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*            *D*---H    H⋯*A*      *D*⋯*A*     *D*---H⋯*A*
  ---------------------- ---------- ---------- ----------- -------------
  N1---H1⋯O22            0.99 (3)   1.66 (2)   2.634 (3)   167 (2)
  C2---H2*A*⋯O25^i^      0.97       2.50       3.444 (3)   163
  C11---H11*A*⋯O14^ii^   0.97       2.49       3.358 (4)   150

Symmetry codes: (i) ; (ii) .

###### Experimental details

  -------------------------------------------------------------------------- ------------------------------------------------------------------------
  Crystal data                                                               
  Chemical formula                                                           C~32~H~40~NO~2~·C~7~H~3~N~2~O~6~
  *M* ~r~                                                                    681.76
  Crystal system, space group                                                Monoclinic, *P*2~1~/*c*
  Temperature (K)                                                            293
  *a*, *b*, *c* (Å)                                                          5.9168 (3), 28.3733 (12), 21.0782 (11)
  β (°)                                                                      97.836 (5)
  *V* (Å^3^)                                                                 3505.6 (3)
  *Z*                                                                        4
  Radiation type                                                             Mo *K*α
  μ (mm^−1^)                                                                 0.09
  Crystal size (mm)                                                          0.23 × 0.21 × 0.18
                                                                             
  Data collection                                                            
  Diffractometer                                                             Rigaku Saturn724
  Absorption correction                                                      Multi-scan (*SADABS*; Krause *et al.*, 2015[@bb7])
  *T* ~min~, *T* ~max~                                                       0.956, 0.984
  No. of measured, independent and observed \[*I* \> 2σ(*I*)\] reflections   40112, 7331, 4388
  *R* ~int~                                                                  0.061
  (sin θ/λ)~max~ (Å^−1^)                                                     0.629
                                                                             
  Refinement                                                                 
  *R*\[*F* ^2^ \> 2σ(*F* ^2^)\], *wR*(*F* ^2^), *S*                          0.065, 0.179, 1.05
  No. of reflections                                                         7331
  No. of parameters                                                          470
  No. of restraints                                                          22
  H-atom treatment                                                           H atoms treated by a mixture of independent and constrained refinement
  Δρ~max~, Δρ~min~ (e Å^−3^)                                                 0.20, −0.25
  -------------------------------------------------------------------------- ------------------------------------------------------------------------

Computer programs: *CrystalClear* (Rigaku, 2011[@bb8]), *SHELXS86* (Sheldrick, 2008[@bb11]), *SHELXL2014* (Sheldrick, 2015[@bb12]) and *PLATON* (Spek, 2009[@bb13]).
