Related literature {#sec1}
==================

For background to the chemistry of substituted pyridines, see: Pozharski *et al.* (1997[@bb11]); Katritzky *et al.* (1996[@bb10]). For related structures, see: Chao *et al.* (1975[@bb3]); Gellert & Hsu (1988[@bb6]); Demir *et al.* (2005[@bb5]); Jebas *et al.* (2006[@bb7]); Rademeyer (2007[@bb12]); Windholz (1976[@bb16]). For details of hydrogen bonding, see: Jeffrey & Saenger (1991[@bb9]); Jeffrey (1997[@bb8]); Scheiner (1997[@bb13]). For hydrogen-bond motifs, see: Bernstein *et al.* (1995[@bb1]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[@bb4]).

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~5~H~7~N~2~ ^+^·C~2~F~3~O~2~ ^−^*M* *~r~* = 208.15Monoclinic,*a* = 11.4641 (15) Å*b* = 10.0221 (13) Å*c* = 29.928 (4) Åβ = 92.918 (3)°*V* = 3434.1 (8) Å^3^*Z* = 16Mo *K*α radiationμ = 0.16 mm^−1^*T* = 100 K0.35 × 0.17 × 0.04 mm

### Data collection {#sec2.1.2}

Bruker APEX DUO CCD area-detector diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2009[@bb2]) *T* ~min~ = 0.947, *T* ~max~ = 0.99428669 measured reflections6732 independent reflections4154 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.072

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.044*wR*(*F* ^2^) = 0.141*S* = 1.026732 reflections617 parametersAll H-atom parameters refinedΔρ~max~ = 0.44 e Å^−3^Δρ~min~ = −0.44 e Å^−3^

 {#d5e873}

Data collection: *APEX2* (Bruker, 2009[@bb2]); cell refinement: *SAINT* (Bruker, 2009[@bb2]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb14]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *SHELXTL*; software used to prepare material for publication: *SHELXTL* and *PLATON* (Spek, 2009[@bb15]).

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536810006392/ci5036sup1.cif](http://dx.doi.org/10.1107/S1600536810006392/ci5036sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536810006392/ci5036Isup2.hkl](http://dx.doi.org/10.1107/S1600536810006392/ci5036Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?ci5036&file=ci5036sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?ci5036sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?ci5036&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [CI5036](http://scripts.iucr.org/cgi-bin/sendsup?ci5036)).

MH and HKF thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

Comment
=======

Pyridine and its derivatives play an important role in heterocyclic chemistry (Pozharski *et al.*, 1997; Katritzky *et al.*, 1996). They are often involved in hydrogen-bond interactions (Jeffrey & Saenger, 1991; Jeffrey, 1997; Scheiner, 1997). 2-Aminopyridine is used in the manufacture of pharmaceuticals, especially antihistaminic drugs (Windholz, 1976). The crystal structures of 2-aminopyridine (Chao *et al.*, 1975), 2-aminopyridinium salicylate (Gellert & Hsu, 1988), 2-amino-pyridinium dihydrogenphosphate (Demir *et al.*, 2005), bis(2-aminopyridinium) sulfate (Jebas *et al.*, 2006) and 2-aminopyridinium nitrate (Rademeyer, 2007) have been reported in the literature. The crystal structure determination of the title compound was undertaken to study the hydrogen bonding interactions in it.

The asymmetric unit of the title compound consists of four crystallographically independent 2-aminopyridinium cations (A, B, C & D) and four trifluoroacetate anions (A, B, C & D) (Fig. 1). Each 2-aminopyridinium cation is planar, with a maximum deviation of 0.017 (3) Å for atom N2A (molecule A), 0.007 (2) Å for atom C3B (molecule B), 0.007 (2) Å for atom N1C (molecule C) and 0.008 (3) Å for atom C5D (molecule D).

In the crystal structure (Fig. 2), carboxylate groups of A, B, C and D trifluoroacetate anions interact with two N--H groups of D, C, A and B 2-aminopyridinium cations, respectively, via pairs of N---H···O hydrogen bonds generating *R*~2~^2^(8) motifs (Bernstein *et al.*, 1995). The ionic pairs are linked into chains along \[100\] by N---H···O hydrogen bonds involving the remaining N--H groups. The crystal structure is further stabilized by C---H···O and C---H···F hydrogen bonds (Table 1) and π···π interactions involving the N1A/C1A--C5A pyridine rings at (x, y, z) and (1-x, 1-y, -z) with a centoid-to-centroid separation of 3.6007 (17) Å.

Experimental {#experimental}
============

To a hot methanol solution (20 ml) of 2-aminopyridine (47 mg, Aldrich) was added a few drops of trifluoroacetic acid. The solution was warmed over a water bath for a few minutes. The resulting solution was allowed to cool slowly to room temperature. Crystals of the title compound appeared from the mother liquor after a few days.

Refinement {#refinement}
==========

All the H atoms were located in a difference Fourier map and allowed to refine freely \[N--H = 0.83 (4)--1.02 (4) Å, C--H = 0.91 (3)--1.08 (3) Å\].

Figures
=======

![The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.](e-66-0o691-fig1){#Fap1}

![The crystal packing of the title compound, showing hydrogen-bonded (dashed lines) networks.](e-66-0o691-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  --------------------------------- ---------------------------------------
  C~5~H~7~N~2~^+^·C~2~F~3~O~2~^−^   *F*(000) = 1696
  *M~r~* = 208.15                   *D*~x~ = 1.610 Mg m^−3^
  Monoclinic, *P*2~1~/*c*           Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc              Cell parameters from 3066 reflections
  *a* = 11.4641 (15) Å              θ = 2.7--24.0°
  *b* = 10.0221 (13) Å              µ = 0.16 mm^−1^
  *c* = 29.928 (4) Å                *T* = 100 K
  β = 92.918 (3)°                   Plate, colourless
  *V* = 3434.1 (8) Å^3^             0.35 × 0.17 × 0.04 mm
  *Z* = 16                          
  --------------------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ------------------------------------------------------------ --------------------------------------
  Bruker APEX DUO CCD area-detector diffractometer             6732 independent reflections
  Radiation source: fine-focus sealed tube                     4154 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.072
  φ and ω scans                                                θ~max~ = 26.0°, θ~min~ = 1.4°
  Absorption correction: multi-scan (*SADABS*; Bruker, 2009)   *h* = −14→12
  *T*~min~ = 0.947, *T*~max~ = 0.994                           *k* = −12→12
  28669 measured reflections                                   *l* = −36→36
  ------------------------------------------------------------ --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- ------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.044   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.141                  All H-atom parameters refined
  *S* = 1.02                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.072*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  6732 reflections                      (Δ/σ)~max~ = 0.001
  617 parameters                        Δρ~max~ = 0.44 e Å^−3^
  0 restraints                          Δρ~min~ = −0.44 e Å^−3^
  ------------------------------------- ------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
  Geometry. All s.u.\'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.\'s are taken into account individually in the estimation of s.u.\'s in distances, angles and torsion angles; correlations between s.u.\'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.\'s is used for estimating s.u.\'s involving l.s. planes.
  Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ \> 2σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
  ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

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

  ------ --------------- -------------- -------------- -------------------- --
         *x*             *y*            *z*            *U*~iso~\*/*U*~eq~   
  N1A    0.53238 (18)    0.6375 (2)     0.03514 (8)    0.0211 (5)           
  N2A    0.7286 (2)      0.6627 (3)     0.02401 (9)    0.0266 (6)           
  C1A    0.4393 (2)      0.5710 (3)     0.05182 (10)   0.0248 (7)           
  C2A    0.4546 (3)      0.4564 (3)     0.07439 (10)   0.0271 (7)           
  C3A    0.5680 (2)      0.4031 (3)     0.08038 (10)   0.0246 (7)           
  C4A    0.6604 (2)      0.4684 (3)     0.06365 (10)   0.0248 (7)           
  C5A    0.6430 (2)      0.5902 (3)     0.04029 (9)    0.0218 (6)           
  F1A    −0.04773 (14)   0.44273 (16)   0.07172 (5)    0.0314 (4)           
  F2A    0.06503 (16)    0.56750 (19)   0.11269 (6)    0.0419 (5)           
  F3A    0.13664 (14)    0.40701 (17)   0.07542 (6)    0.0347 (4)           
  O1A    −0.01983 (15)   0.65268 (18)   0.01836 (6)    0.0218 (4)           
  O2A    0.17434 (15)    0.6235 (2)     0.02589 (7)    0.0289 (5)           
  C6A    0.0564 (2)      0.5042 (3)     0.07342 (9)    0.0231 (6)           
  C7A    0.0723 (2)      0.6020 (3)     0.03494 (9)    0.0187 (6)           
  N1B    0.25015 (19)    0.0690 (2)     0.22063 (8)    0.0223 (5)           
  N2B    0.4426 (2)      0.0544 (3)     0.24561 (10)   0.0327 (7)           
  C1B    0.1593 (3)      0.1252 (3)     0.19635 (10)   0.0290 (7)           
  C2B    0.1754 (3)      0.2363 (3)     0.17180 (11)   0.0352 (8)           
  C3B    0.2877 (3)      0.2902 (3)     0.17187 (11)   0.0365 (8)           
  C4B    0.3786 (3)      0.2344 (3)     0.19497 (11)   0.0342 (8)           
  C5B    0.3600 (2)      0.1179 (3)     0.22101 (10)   0.0265 (7)           
  F1B    0.19140 (15)    0.79602 (17)   0.16527 (6)    0.0357 (4)           
  F2B    0.31202 (16)    0.64578 (17)   0.14540 (6)    0.0391 (5)           
  F3B    0.36394 (14)    0.78893 (16)   0.19615 (6)    0.0326 (4)           
  O1B    0.12827 (16)    0.5810 (2)     0.21178 (7)    0.0306 (5)           
  O2B    0.30890 (15)    0.57592 (19)   0.24392 (6)    0.0237 (5)           
  C6B    0.2742 (2)      0.7125 (3)     0.18099 (10)   0.0240 (7)           
  C7B    0.2322 (2)      0.6146 (3)     0.21597 (9)    0.0220 (6)           
  N1C    0.97689 (18)    0.1324 (2)     0.03769 (8)    0.0195 (5)           
  N2C    0.7775 (2)      0.1534 (3)     0.02793 (9)    0.0234 (6)           
  C1C    1.0764 (2)      0.0718 (3)     0.05421 (10)   0.0233 (7)           
  C2C    1.0705 (3)      −0.0409 (3)    0.07859 (10)   0.0259 (7)           
  C3C    0.9596 (3)      −0.0928 (3)    0.08655 (10)   0.0259 (7)           
  C4C    0.8602 (2)      −0.0311 (3)    0.07060 (10)   0.0229 (6)           
  C5C    0.8686 (2)      0.0864 (3)     0.04501 (9)    0.0187 (6)           
  F1C    0.70647 (15)    0.14098 (17)   0.14889 (6)    0.0361 (5)           
  F2C    0.83699 (16)    0.28461 (17)   0.13276 (6)    0.0383 (5)           
  F3C    0.87288 (13)    0.14044 (16)   0.18453 (5)    0.0290 (4)           
  O1C    0.64277 (16)    0.3622 (2)     0.19178 (7)    0.0296 (5)           
  O2C    0.81484 (15)    0.35674 (19)   0.23072 (6)    0.0243 (5)           
  C6C    0.7897 (2)      0.2205 (3)     0.16693 (9)    0.0235 (7)           
  C7C    0.7438 (2)      0.3217 (3)     0.20015 (9)    0.0215 (6)           
  N1D    0.75292 (18)    0.8656 (2)     0.20606 (8)    0.0203 (5)           
  N2D    0.9457 (2)      0.8664 (3)     0.23238 (9)    0.0272 (6)           
  C1D    0.6606 (2)      0.8152 (3)     0.18099 (10)   0.0252 (7)           
  C2D    0.6725 (3)      0.7041 (3)     0.15644 (10)   0.0293 (7)           
  C3D    0.7819 (3)      0.6428 (3)     0.15695 (10)   0.0283 (7)           
  C4D    0.8744 (3)      0.6922 (3)     0.18151 (10)   0.0253 (7)           
  C5D    0.8595 (2)      0.8081 (3)     0.20725 (9)    0.0216 (6)           
  F1D    0.38550 (14)    0.89359 (17)   0.07557 (6)    0.0363 (5)           
  F2D    0.45932 (18)    1.0533 (2)     0.11547 (6)    0.0484 (5)           
  F3D    0.56876 (14)    0.93681 (17)   0.07456 (6)    0.0355 (5)           
  O1D    0.33350 (16)    1.1182 (2)     0.02989 (8)    0.0394 (6)           
  O2D    0.52497 (15)    1.14436 (19)   0.02069 (6)    0.0238 (5)           
  C6D    0.4630 (2)      0.9937 (3)     0.07548 (10)   0.0261 (7)           
  C7D    0.4378 (2)      1.0945 (3)     0.03804 (10)   0.0245 (7)           
  H1A    0.364 (3)       0.615 (3)      0.0418 (9)     0.026 (8)\*          
  H2A    0.383 (3)       0.406 (3)      0.0863 (11)    0.050 (10)\*         
  H3A    0.579 (3)       0.315 (3)      0.0972 (10)    0.037 (9)\*          
  H4A    0.748 (3)       0.435 (3)      0.0678 (9)     0.031 (8)\*          
  H1NA   0.525 (2)       0.710 (3)      0.0166 (9)     0.016 (7)\*          
  H2NA   0.697 (4)       0.743 (4)      0.0063 (13)    0.080 (14)\*         
  H3NA   0.799 (3)       0.641 (3)      0.0250 (11)    0.052 (11)\*         
  H1B    0.076 (3)       0.081 (3)      0.2000 (10)    0.042 (9)\*          
  H2B    0.100 (3)       0.280 (3)      0.1548 (11)    0.057 (11)\*         
  H3B    0.297 (3)       0.364 (3)      0.1548 (11)    0.041 (10)\*         
  H4B    0.466 (3)       0.266 (3)      0.1957 (10)    0.044 (9)\*          
  H1NB   0.240 (3)       −0.011 (3)     0.2385 (9)     0.031 (9)\*          
  H2NB   0.430 (3)       −0.007 (4)     0.2673 (11)    0.043 (11)\*         
  H3NB   0.511 (3)       0.087 (3)      0.2509 (10)    0.038 (10)\*         
  H1C    1.148 (2)       0.110 (3)      0.0459 (9)     0.022 (8)\*          
  H2C    1.139 (3)       −0.086 (3)     0.0906 (10)    0.035 (9)\*          
  H3C    0.955 (2)       −0.174 (3)     0.1037 (10)    0.029 (8)\*          
  H4C    0.787 (3)       −0.064 (3)     0.0765 (9)     0.027 (8)\*          
  H1NC   0.984 (3)       0.202 (3)      0.0213 (10)    0.029 (9)\*          
  H2NC   0.792 (3)       0.222 (3)      0.0099 (11)    0.049 (11)\*         
  H3NC   0.701 (3)       0.121 (4)      0.0304 (12)    0.062 (12)\*         
  H1D    0.583 (2)       0.864 (3)      0.1846 (9)     0.023 (7)\*          
  H2D    0.603 (3)       0.670 (3)      0.1391 (10)    0.034 (8)\*          
  H3D    0.791 (2)       0.560 (3)      0.1406 (9)     0.027 (8)\*          
  H4D    0.961 (2)       0.650 (3)      0.1830 (9)     0.027 (8)\*          
  H1ND   0.746 (2)       0.938 (3)      0.2247 (9)     0.026 (8)\*          
  H2ND   0.940 (2)       0.937 (3)      0.2533 (10)    0.026 (8)\*          
  H3ND   1.009 (3)       0.826 (3)      0.2377 (10)    0.032 (9)\*          
  ------ --------------- -------------- -------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  N1A   0.0145 (12)   0.0229 (14)   0.0259 (14)   0.0006 (10)    0.0017 (10)    −0.0020 (12)
  N2A   0.0104 (12)   0.0265 (15)   0.0431 (17)   0.0006 (10)    0.0041 (11)    −0.0005 (12)
  C1A   0.0138 (14)   0.0332 (18)   0.0275 (17)   −0.0003 (12)   0.0023 (12)    −0.0038 (14)
  C2A   0.0248 (16)   0.0342 (18)   0.0227 (17)   −0.0062 (13)   0.0035 (12)    −0.0053 (14)
  C3A   0.0236 (15)   0.0272 (17)   0.0230 (17)   −0.0034 (13)   0.0014 (12)    −0.0061 (14)
  C4A   0.0209 (15)   0.0246 (16)   0.0285 (17)   0.0018 (12)    −0.0021 (12)   −0.0022 (14)
  C5A   0.0171 (14)   0.0240 (16)   0.0246 (16)   −0.0012 (11)   0.0020 (11)    −0.0063 (13)
  F1A   0.0229 (9)    0.0390 (11)   0.0329 (10)   −0.0065 (7)    0.0054 (7)     0.0108 (8)
  F2A   0.0512 (12)   0.0532 (13)   0.0209 (10)   −0.0013 (9)    −0.0012 (8)    −0.0068 (9)
  F3A   0.0275 (9)    0.0362 (10)   0.0404 (11)   0.0104 (8)     0.0016 (8)     0.0155 (9)
  O1A   0.0134 (9)    0.0236 (11)   0.0283 (11)   0.0014 (8)     0.0007 (8)     0.0043 (9)
  O2A   0.0123 (10)   0.0337 (12)   0.0409 (13)   −0.0013 (8)    0.0015 (8)     0.0128 (10)
  C6A   0.0167 (14)   0.0278 (17)   0.0247 (17)   −0.0001 (12)   −0.0005 (11)   0.0022 (14)
  C7A   0.0153 (14)   0.0185 (15)   0.0222 (15)   −0.0001 (11)   −0.0010 (11)   −0.0006 (12)
  N1B   0.0181 (12)   0.0207 (13)   0.0285 (14)   −0.0021 (10)   0.0046 (10)    0.0000 (11)
  N2B   0.0184 (14)   0.0388 (17)   0.0407 (18)   −0.0071 (12)   0.0006 (12)    −0.0067 (15)
  C1B   0.0272 (16)   0.0269 (17)   0.0329 (19)   0.0056 (13)    0.0017 (13)    −0.0004 (14)
  C2B   0.046 (2)     0.0289 (19)   0.0311 (19)   0.0078 (15)    0.0098 (15)    0.0050 (15)
  C3B   0.056 (2)     0.0247 (19)   0.031 (2)     0.0006 (16)    0.0200 (16)    0.0015 (16)
  C4B   0.043 (2)     0.0269 (18)   0.0346 (19)   −0.0140 (15)   0.0184 (15)    −0.0088 (15)
  C5B   0.0237 (16)   0.0253 (17)   0.0312 (18)   −0.0036 (13)   0.0088 (13)    −0.0102 (14)
  F1B   0.0408 (11)   0.0322 (10)   0.0334 (11)   0.0069 (8)     −0.0045 (8)    0.0080 (8)
  F2B   0.0535 (12)   0.0365 (11)   0.0288 (11)   0.0006 (9)     0.0179 (8)     −0.0056 (9)
  F3B   0.0310 (10)   0.0300 (10)   0.0369 (11)   −0.0055 (8)    0.0029 (8)     0.0029 (8)
  O1B   0.0203 (11)   0.0425 (13)   0.0286 (12)   −0.0044 (9)    −0.0027 (8)    0.0026 (10)
  O2B   0.0171 (10)   0.0271 (11)   0.0267 (11)   0.0021 (8)     −0.0008 (8)    0.0026 (9)
  C6B   0.0215 (15)   0.0244 (16)   0.0258 (17)   0.0021 (12)    −0.0011 (12)   −0.0041 (13)
  C7B   0.0207 (15)   0.0248 (16)   0.0205 (16)   0.0028 (12)    0.0023 (12)    −0.0052 (13)
  N1C   0.0163 (12)   0.0183 (13)   0.0239 (14)   0.0000 (9)     0.0024 (10)    0.0029 (11)
  N2C   0.0123 (12)   0.0249 (15)   0.0330 (16)   −0.0029 (10)   0.0013 (10)    0.0035 (12)
  C1C   0.0156 (15)   0.0299 (17)   0.0245 (16)   0.0007 (12)    0.0013 (11)    0.0016 (13)
  C2C   0.0219 (15)   0.0303 (18)   0.0253 (17)   0.0084 (13)    0.0003 (12)    0.0050 (14)
  C3C   0.0346 (17)   0.0183 (16)   0.0254 (17)   0.0011 (13)    0.0074 (13)    0.0061 (13)
  C4C   0.0198 (15)   0.0208 (16)   0.0287 (17)   −0.0012 (12)   0.0071 (12)    0.0006 (13)
  C5C   0.0159 (14)   0.0187 (15)   0.0216 (15)   −0.0028 (11)   0.0025 (11)    −0.0027 (12)
  F1C   0.0356 (10)   0.0326 (10)   0.0391 (11)   −0.0034 (8)    −0.0100 (8)    −0.0083 (9)
  F2C   0.0545 (12)   0.0334 (11)   0.0283 (11)   −0.0007 (9)    0.0146 (8)     0.0082 (8)
  F3C   0.0258 (9)    0.0295 (10)   0.0316 (10)   0.0060 (7)     0.0007 (7)     0.0014 (8)
  O1C   0.0192 (11)   0.0336 (12)   0.0354 (13)   0.0032 (9)     −0.0037 (9)    0.0000 (10)
  O2C   0.0172 (10)   0.0266 (11)   0.0288 (12)   −0.0003 (8)    −0.0025 (8)    −0.0050 (9)
  C6C   0.0214 (15)   0.0242 (16)   0.0247 (16)   −0.0021 (12)   −0.0011 (12)   0.0063 (13)
  C7C   0.0197 (15)   0.0220 (16)   0.0228 (16)   −0.0031 (11)   0.0017 (12)    0.0039 (12)
  N1D   0.0162 (12)   0.0202 (13)   0.0244 (14)   0.0004 (10)    0.0007 (10)    −0.0004 (11)
  N2D   0.0155 (13)   0.0337 (16)   0.0322 (16)   0.0024 (11)    −0.0021 (11)   0.0024 (13)
  C1D   0.0200 (15)   0.0279 (17)   0.0277 (17)   −0.0038 (12)   0.0007 (12)    0.0021 (14)
  C2D   0.0313 (17)   0.0258 (17)   0.0310 (18)   −0.0058 (13)   0.0026 (14)    −0.0024 (14)
  C3D   0.0374 (18)   0.0200 (17)   0.0283 (18)   −0.0011 (14)   0.0080 (14)    −0.0003 (14)
  C4D   0.0295 (17)   0.0217 (16)   0.0256 (17)   0.0053 (13)    0.0093 (13)    0.0057 (13)
  C5D   0.0199 (15)   0.0238 (16)   0.0214 (16)   0.0005 (11)    0.0052 (11)    0.0088 (12)
  F1D   0.0292 (10)   0.0351 (10)   0.0449 (12)   −0.0034 (8)    0.0047 (8)     0.0097 (9)
  F2D   0.0641 (14)   0.0538 (13)   0.0277 (11)   0.0036 (10)    0.0064 (9)     −0.0105 (10)
  F3D   0.0227 (9)    0.0446 (11)   0.0386 (11)   0.0077 (8)     −0.0039 (7)    0.0054 (9)
  O1D   0.0132 (11)   0.0437 (14)   0.0617 (16)   0.0031 (9)     0.0068 (10)    0.0201 (12)
  O2D   0.0146 (10)   0.0283 (11)   0.0287 (12)   −0.0023 (8)    0.0046 (8)     −0.0017 (9)
  C6D   0.0208 (15)   0.0291 (17)   0.0287 (18)   −0.0018 (12)   0.0025 (12)    −0.0077 (14)
  C7D   0.0149 (14)   0.0272 (17)   0.0315 (17)   0.0002 (12)    0.0036 (12)    −0.0035 (14)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

Geometric parameters (Å, °) {#tablewrapgeomlong}
===========================

  ----------------------- ------------ ----------------------- ------------
  N1A---C5A               1.355 (3)    N1C---C5C               1.353 (3)
  N1A---C1A               1.373 (4)    N1C---C1C               1.363 (3)
  N1A---H1NA              0.92 (3)     N1C---H1NC              0.86 (3)
  N2A---C5A               1.334 (4)    N2C---C5C               1.323 (3)
  N2A---H2NA              1.02 (4)     N2C---H2NC              0.90 (3)
  N2A---H3NA              0.83 (4)     N2C---H3NC              0.94 (4)
  C1A---C2A               1.340 (4)    C1C---C2C               1.348 (4)
  C1A---H1A               1.00 (3)     C1C---H1C               0.95 (3)
  C2A---C3A               1.409 (4)    C2C---C3C               1.406 (4)
  C2A---H2A               1.04 (3)     C2C---H2C               0.96 (3)
  C3A---C4A               1.362 (4)    C3C---C4C               1.361 (4)
  C3A---H3A               1.02 (3)     C3C---H3C               0.97 (3)
  C4A---C5A               1.416 (4)    C4C---C5C               1.410 (4)
  C4A---H4A               1.06 (3)     C4C---H4C               0.92 (3)
  F1A---C6A               1.342 (3)    F1C---C6C               1.336 (3)
  F2A---C6A               1.335 (3)    F2C---C6C               1.345 (3)
  F3A---C6A               1.339 (3)    F3C---C6C               1.334 (3)
  O1A---C7A               1.252 (3)    O1C---C7C               1.240 (3)
  O2A---C7A               1.233 (3)    O2C---C7C               1.244 (3)
  C6A---C7A               1.531 (4)    C6C---C7C               1.533 (4)
  N1B---C5B               1.351 (3)    N1D---C5D               1.349 (3)
  N1B---C1B               1.361 (4)    N1D---C1D               1.363 (3)
  N1B---H1NB              0.97 (3)     N1D---H1ND              0.92 (3)
  N2B---C5B               1.331 (4)    N2D---C5D               1.346 (4)
  N2B---H2NB              0.91 (3)     N2D---H2ND              0.95 (3)
  N2B---H3NB              0.86 (3)     N2D---H3ND              0.84 (3)
  C1B---C2B               1.352 (4)    C1D---C2D               1.345 (4)
  C1B---H1B               1.06 (3)     C1D---H1D               1.03 (3)
  C2B---C3B               1.396 (5)    C2D---C3D               1.395 (4)
  C2B---H2B               1.07 (3)     C2D---H2D               0.99 (3)
  C3B---C4B               1.342 (5)    C3D---C4D               1.353 (4)
  C3B---H3B               0.91 (3)     C3D---H3D               0.97 (3)
  C4B---C5B               1.426 (4)    C4D---C5D               1.409 (4)
  C4B---H4B               1.05 (3)     C4D---H4D               1.08 (3)
  F1B---C6B               1.334 (3)    F1D---C6D               1.340 (3)
  F2B---C6B               1.348 (3)    F2D---C6D               1.340 (3)
  F3B---C6B               1.343 (3)    F3D---C6D               1.341 (3)
  O1B---C7B               1.238 (3)    O1D---C7D               1.231 (3)
  O2B---C7B               1.245 (3)    O2D---C7D               1.253 (3)
  C6B---C7B               1.530 (4)    C6D---C7D               1.526 (4)
                                                               
  C5A---N1A---C1A         121.9 (3)    C5C---N1C---C1C         123.2 (3)
  C5A---N1A---H1NA        113.5 (17)   C5C---N1C---H1NC        119 (2)
  C1A---N1A---H1NA        124.1 (17)   C1C---N1C---H1NC        118 (2)
  C5A---N2A---H2NA        112 (2)      C5C---N2C---H2NC        117 (2)
  C5A---N2A---H3NA        125 (2)      C5C---N2C---H3NC        121 (2)
  H2NA---N2A---H3NA       123 (3)      H2NC---N2C---H3NC       121 (3)
  C2A---C1A---N1A         121.1 (3)    C2C---C1C---N1C         120.4 (3)
  C2A---C1A---H1A         127.9 (16)   C2C---C1C---H1C         123.0 (16)
  N1A---C1A---H1A         110.7 (16)   N1C---C1C---H1C         116.5 (16)
  C1A---C2A---C3A         119.0 (3)    C1C---C2C---C3C         118.2 (3)
  C1A---C2A---H2A         120.0 (18)   C1C---C2C---H2C         122.2 (18)
  C3A---C2A---H2A         120.9 (18)   C3C---C2C---H2C         119.6 (18)
  C4A---C3A---C2A         120.1 (3)    C4C---C3C---C2C         121.4 (3)
  C4A---C3A---H3A         121.1 (17)   C4C---C3C---H3C         119.9 (17)
  C2A---C3A---H3A         118.8 (17)   C2C---C3C---H3C         118.7 (17)
  C3A---C4A---C5A         120.2 (3)    C3C---C4C---C5C         119.4 (3)
  C3A---C4A---H4A         123.7 (16)   C3C---C4C---H4C         121.2 (18)
  C5A---C4A---H4A         116.1 (16)   C5C---C4C---H4C         119.4 (18)
  N2A---C5A---N1A         118.0 (3)    N2C---C5C---N1C         118.5 (3)
  N2A---C5A---C4A         124.2 (3)    N2C---C5C---C4C         124.0 (3)
  N1A---C5A---C4A         117.8 (3)    N1C---C5C---C4C         117.5 (2)
  F2A---C6A---F3A         106.7 (2)    F3C---C6C---F1C         106.4 (2)
  F2A---C6A---F1A         106.1 (2)    F3C---C6C---F2C         106.2 (2)
  F3A---C6A---F1A         106.0 (2)    F1C---C6C---F2C         106.6 (2)
  F2A---C6A---C7A         110.6 (2)    F3C---C6C---C7C         113.8 (2)
  F3A---C6A---C7A         113.1 (2)    F1C---C6C---C7C         113.3 (2)
  F1A---C6A---C7A         113.9 (2)    F2C---C6C---C7C         110.0 (2)
  O2A---C7A---O1A         129.3 (3)    O1C---C7C---O2C         128.8 (3)
  O2A---C7A---C6A         115.3 (2)    O1C---C7C---C6C         115.7 (2)
  O1A---C7A---C6A         115.3 (2)    O2C---C7C---C6C         115.5 (2)
  C5B---N1B---C1B         122.8 (3)    C5D---N1D---C1D         122.2 (3)
  C5B---N1B---H1NB        115.4 (17)   C5D---N1D---H1ND        115.3 (18)
  C1B---N1B---H1NB        121.8 (17)   C1D---N1D---H1ND        122.3 (18)
  C5B---N2B---H2NB        126 (2)      C5D---N2D---H2ND        128.0 (17)
  C5B---N2B---H3NB        122 (2)      C5D---N2D---H3ND        120 (2)
  H2NB---N2B---H3NB       108 (3)      H2ND---N2D---H3ND       109 (3)
  C2B---C1B---N1B         120.6 (3)    C2D---C1D---N1D         120.6 (3)
  C2B---C1B---H1B         123.2 (16)   C2D---C1D---H1D         124.2 (15)
  N1B---C1B---H1B         116.0 (16)   N1D---C1D---H1D         115.0 (15)
  C1B---C2B---C3B         118.0 (3)    C1D---C2D---C3D         118.3 (3)
  C1B---C2B---H2B         117.9 (19)   C1D---C2D---H2D         118.3 (18)
  C3B---C2B---H2B         124.0 (19)   C3D---C2D---H2D         123.4 (18)
  C4B---C3B---C2B         122.0 (3)    C4D---C3D---C2D         121.6 (3)
  C4B---C3B---H3B         121 (2)      C4D---C3D---H3D         118.7 (17)
  C2B---C3B---H3B         117 (2)      C2D---C3D---H3D         119.6 (17)
  C3B---C4B---C5B         119.3 (3)    C3D---C4D---C5D         119.0 (3)
  C3B---C4B---H4B         126.8 (17)   C3D---C4D---H4D         124.8 (14)
  C5B---C4B---H4B         113.9 (17)   C5D---C4D---H4D         116.2 (14)
  N2B---C5B---N1B         117.9 (3)    N2D---C5D---N1D         117.9 (3)
  N2B---C5B---C4B         124.9 (3)    N2D---C5D---C4D         123.9 (3)
  N1B---C5B---C4B         117.3 (3)    N1D---C5D---C4D         118.2 (3)
  F1B---C6B---F3B         106.3 (2)    F1D---C6D---F2D         106.3 (2)
  F1B---C6B---F2B         106.5 (2)    F1D---C6D---F3D         106.4 (2)
  F3B---C6B---F2B         106.2 (2)    F2D---C6D---F3D         106.1 (2)
  F1B---C6B---C7B         113.6 (2)    F1D---C6D---C7D         113.4 (2)
  F3B---C6B---C7B         113.4 (2)    F2D---C6D---C7D         110.3 (2)
  F2B---C6B---C7B         110.4 (2)    F3D---C6D---C7D         113.8 (2)
  O1B---C7B---O2B         128.8 (3)    O1D---C7D---O2D         128.9 (3)
  O1B---C7B---C6B         116.1 (2)    O1D---C7D---C6D         114.7 (3)
  O2B---C7B---C6B         115.0 (2)    O2D---C7D---C6D         116.3 (2)
                                                               
  C5A---N1A---C1A---C2A   0.6 (4)      C5C---N1C---C1C---C2C   1.1 (4)
  N1A---C1A---C2A---C3A   −0.9 (4)     N1C---C1C---C2C---C3C   −0.3 (4)
  C1A---C2A---C3A---C4A   0.5 (4)      C1C---C2C---C3C---C4C   −0.6 (5)
  C2A---C3A---C4A---C5A   0.2 (4)      C2C---C3C---C4C---C5C   0.9 (4)
  C1A---N1A---C5A---N2A   −178.4 (3)   C1C---N1C---C5C---N2C   179.2 (3)
  C1A---N1A---C5A---C4A   0.0 (4)      C1C---N1C---C5C---C4C   −0.8 (4)
  C3A---C4A---C5A---N2A   177.9 (3)    C3C---C4C---C5C---N2C   179.8 (3)
  C3A---C4A---C5A---N1A   −0.5 (4)     C3C---C4C---C5C---N1C   −0.2 (4)
  F2A---C6A---C7A---O2A   85.4 (3)     F3C---C6C---C7C---O1C   −154.3 (2)
  F3A---C6A---C7A---O2A   −34.1 (3)    F1C---C6C---C7C---O1C   −32.5 (3)
  F1A---C6A---C7A---O2A   −155.3 (2)   F2C---C6C---C7C---O1C   86.7 (3)
  F2A---C6A---C7A---O1A   −92.0 (3)    F3C---C6C---C7C---O2C   28.9 (3)
  F3A---C6A---C7A---O1A   148.5 (2)    F1C---C6C---C7C---O2C   150.7 (2)
  F1A---C6A---C7A---O1A   27.4 (3)     F2C---C6C---C7C---O2C   −90.2 (3)
  C5B---N1B---C1B---C2B   −1.3 (4)     C5D---N1D---C1D---C2D   0.5 (4)
  N1B---C1B---C2B---C3B   0.5 (5)      N1D---C1D---C2D---C3D   −0.7 (4)
  C1B---C2B---C3B---C4B   0.7 (5)      C1D---C2D---C3D---C4D   0.3 (5)
  C2B---C3B---C4B---C5B   −1.3 (5)     C2D---C3D---C4D---C5D   0.2 (4)
  C1B---N1B---C5B---N2B   −179.4 (3)   C1D---N1D---C5D---N2D   178.9 (3)
  C1B---N1B---C5B---C4B   0.7 (4)      C1D---N1D---C5D---C4D   0.0 (4)
  C3B---C4B---C5B---N2B   −179.3 (3)   C3D---C4D---C5D---N2D   −179.1 (3)
  C3B---C4B---C5B---N1B   0.5 (4)      C3D---C4D---C5D---N1D   −0.4 (4)
  F1B---C6B---C7B---O1B   31.0 (3)     F1D---C6D---C7D---O1D   37.8 (4)
  F3B---C6B---C7B---O1B   152.5 (2)    F2D---C6D---C7D---O1D   −81.4 (3)
  F2B---C6B---C7B---O1B   −88.5 (3)    F3D---C6D---C7D---O1D   159.6 (3)
  F1B---C6B---C7B---O2B   −151.5 (2)   F1D---C6D---C7D---O2D   −144.0 (3)
  F3B---C6B---C7B---O2B   −30.0 (3)    F2D---C6D---C7D---O2D   96.8 (3)
  F2B---C6B---C7B---O2B   89.0 (3)     F3D---C6D---C7D---O2D   −22.2 (4)
  ----------------------- ------------ ----------------------- ------------

Hydrogen-bond geometry (Å, °) {#tablewraphbondslong}
=============================

  ----------------------- ---------- ---------- ----------- ---------------
  *D*---H···*A*           *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  N1A---H1NA···O2D^i^     0.92 (3)   1.91 (3)   2.809 (3)   168 (2)
  N2A---H2NA···O1D^i^     1.02 (4)   1.79 (4)   2.795 (4)   169 (4)
  N2A---H3NA···O1A^ii^    0.84 (3)   2.10 (3)   2.899 (3)   160 (3)
  N1B---H1NB···O2C^iii^   0.97 (3)   1.75 (3)   2.704 (3)   166 (3)
  N2B---H2NB···O1C^iii^   0.91 (4)   2.01 (4)   2.892 (4)   164 (3)
  N2B---H3NB···O2B^iii^   0.86 (3)   2.07 (3)   2.858 (3)   154 (3)
  N1C---H1NC···O1A^iv^    0.86 (3)   1.94 (3)   2.789 (3)   172 (3)
  N2C---H2NC···O2A^iv^    0.90 (3)   1.93 (3)   2.827 (4)   177 (3)
  N2C---H3NC···O2D^v^     0.94 (3)   2.04 (3)   2.894 (3)   150 (3)
  N1D---H1ND···O2B^vi^    0.92 (3)   1.80 (3)   2.701 (3)   164 (2)
  N2D---H2ND···O1B^vi^    0.95 (3)   1.97 (3)   2.878 (4)   160 (2)
  N2D---H3ND···O2C^vii^   0.84 (3)   2.21 (3)   2.908 (3)   141 (3)
  C1A---H1A···O2A         1.00 (3)   2.20 (3)   3.141 (3)   155 (2)
  C1B---H1B···F3C^viii^   1.06 (3)   2.43 (3)   3.288 (4)   137 (2)
  C1C---H1C···O1D^ix^     0.95 (2)   2.21 (2)   3.107 (3)   158 (2)
  C4A---H4A···F1A^ii^     1.06 (3)   2.34 (3)   3.352 (3)   159 (2)
  C4B---H4B···O1C         1.05 (3)   2.25 (3)   3.294 (4)   171 (2)
  C4C---H4C···F3D^v^      0.93 (3)   2.50 (3)   3.365 (3)   155 (3)
  C4D---H4D···O1B^ii^     1.08 (2)   2.18 (2)   3.204 (4)   159 (2)
  ----------------------- ---------- ---------- ----------- ---------------

Symmetry codes: (i) −*x*+1, −*y*+2, −*z*; (ii) *x*+1, *y*, *z*; (iii) −*x*+1, *y*−1/2, −*z*+1/2; (iv) −*x*+1, −*y*+1, −*z*; (v) *x*, *y*−1, *z*; (vi) −*x*+1, *y*+1/2, −*z*+1/2; (vii) −*x*+2, *y*+1/2, −*z*+1/2; (viii) *x*−1, *y*, *z*; (ix) *x*+1, *y*−1, *z*.

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*                 *D*---H    H⋯*A*      *D*⋯*A*     *D*---H⋯*A*
  --------------------------- ---------- ---------- ----------- -------------
  N1*A*---H1*NA*⋯O2*D*^i^     0.92 (3)   1.91 (3)   2.809 (3)   168 (2)
  N2*A*---H2*NA*⋯O1*D*^i^     1.02 (4)   1.79 (4)   2.795 (4)   169 (4)
  N2*A*---H3*NA*⋯O1*A*^ii^    0.84 (3)   2.10 (3)   2.899 (3)   160 (3)
  N1*B*---H1*NB*⋯O2*C*^iii^   0.97 (3)   1.75 (3)   2.704 (3)   166 (3)
  N2*B*---H2*NB*⋯O1*C*^iii^   0.91 (4)   2.01 (4)   2.892 (4)   164 (3)
  N2*B*---H3*NB*⋯O2*B*^iii^   0.86 (3)   2.07 (3)   2.858 (3)   154 (3)
  N1*C*---H1*NC*⋯O1*A*^iv^    0.86 (3)   1.94 (3)   2.789 (3)   172 (3)
  N2*C*---H2*NC*⋯O2*A*^iv^    0.90 (3)   1.93 (3)   2.827 (4)   177 (3)
  N2*C*---H3*NC*⋯O2*D*^v^     0.94 (3)   2.04 (3)   2.894 (3)   150 (3)
  N1*D*---H1*ND*⋯O2*B*^vi^    0.92 (3)   1.80 (3)   2.701 (3)   164 (2)
  N2*D*---H2*ND*⋯O1*B*^vi^    0.95 (3)   1.97 (3)   2.878 (4)   160 (2)
  N2*D*---H3*ND*⋯O2*C*^vii^   0.84 (3)   2.21 (3)   2.908 (3)   141 (3)
  C1*A*---H1*A*⋯O2*A*         1.00 (3)   2.20 (3)   3.141 (3)   155 (2)
  C1*B*---H1*B*⋯F3*C*^viii^   1.06 (3)   2.43 (3)   3.288 (4)   137 (2)
  C1*C*---H1*C*⋯O1*D*^ix^     0.95 (2)   2.21 (2)   3.107 (3)   158 (2)
  C4*A*---H4*A*⋯F1*A*^ii^     1.06 (3)   2.34 (3)   3.352 (3)   159 (2)
  C4*B*---H4*B*⋯O1*C*         1.05 (3)   2.25 (3)   3.294 (4)   171 (2)
  C4*C*---H4*C*⋯F3*D*^v^      0.93 (3)   2.50 (3)   3.365 (3)   155 (3)
  C4*D*---H4*D*⋯O1*B*^ii^     1.08 (2)   2.18 (2)   3.204 (4)   159 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .

[^1]: Thomson Reuters ResearcherID: A-3561-2009.
