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

For related structures, see: Brauer & Kottsieper (2003[@bb3]); Curtis & Pasternak (1955[@bb4]). For bond-length data, see: Allen *et al.* (1987[@bb1]). For ring motifs, see: Bernstein *et al.* (1995[@bb2]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

2C~4~H~10~N~3~O~2~ ^+^·SO~4~ ^2−^*M* *~r~* = 360.36Monoclinic,*a* = 9.3021 (12) Å*b* = 11.0081 (11) Å*c* = 17.1063 (13) Åβ = 100.980 (3)°*V* = 1719.6 (3) Å^3^*Z* = 4Mo *K*α radiationμ = 0.24 mm^−1^*T* = 296 K0.24 × 0.18 × 0.15 mm

### Data collection {#sec2.1.2}

Enraf--Nonius CAD-4 diffractometerAbsorption correction: ψ scan (North *et al.*, 1968[@bb9]) *T* ~min~ = 0.946, *T* ~max~ = 0.9673481 measured reflections3481 independent reflections2124 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.0253 standard reflections frequency: 120 min intensity decay: 1.7%

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.045*wR*(*F* ^2^) = 0.108*S* = 1.033481 reflections233 parametersH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.21 e Å^−3^Δρ~min~ = −0.25 e Å^−3^

 {#d5e667}

Data collection: *CAD-4 EXPRESS* (Enraf--Nonius, 1994[@bb5]); cell refinement: *CAD-4 EXPRESS*; data reduction: *XCAD4* (Harms & Wocadlo, 1995[@bb8]); program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb10]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb10]); molecular graphics: *ORTEP-3 for Windows* (Farrugia, 1997[@bb6]) and *PLATON* (Spek, 2009[@bb11]); software used to prepare material for publication: *WinGX* (Farrugia, 1999[@bb7]) and *PLATON* (Spek, 2009[@bb11]).

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S160053680900912X/hk2641sup1.cif](http://dx.doi.org/10.1107/S160053680900912X/hk2641sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S160053680900912X/hk2641Isup2.hkl](http://dx.doi.org/10.1107/S160053680900912X/hk2641Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?hk2641&file=hk2641sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?hk2641sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?hk2641&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [HK2641](http://scripts.iucr.org/cgi-bin/sendsup?hk2641)).

The authors acknowledge the preparative efforts of the late Muhammad Asghar, student of Dr Christy Munir at Quaid-i-Azam University, Islamabad, Pakistan.

Comment
=======

As part of our ongoing studies, we report herein the crystal structure of the title compound, (I).

The crystal structures of 1-carbamoylguanidinium methylphosphonate monohydrate, (II) (Brauer & Kottsieper, 2003) and methylguanidinium nitrate, (III) (Curtis & Pasternak, 1955) have been reported. In the molecule of the title compound (Fig. 1), the bond lengths (Allen *et al.*, 1987) and angles of the diamino(ethoxycarbonylamino)methylium (DEAM) moieties are within normal ranges. DEAM moieties (N1--N3/O5/O6/C1--C4) and (N4--N6/O7/O8/C5--C8) are planar with maximum deviations of 0.043 (2) and -0.322 (3) Å for N2 and N4 atoms, respectively, in which they are oriented at a dihedral angle of 62.30 (4)°. The intramolecular N---H···O hydrogen bonds result in the formations of two planar six-membered rings: A (O5/N2/N3/C1/C2/H2A) and B (O7/N5/N6/C5/C6/H5A). The dihedral angle between them is A/B = 60.38 (3)°. The DEAM moieties are linked to the SO~4~ ion through the intramolecular C---H···O and N---H···O hydrogen bonds (Table 1), forming a R~2~^2^(8) ring motif (Bernstein *et al.*, 1995).

In the crystal structure, intermolecular N---H···O and C---H···O hydrogen bonds (Table 1) link the molecules into a three dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.

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

For the preparation of the title compound, 1-cyanoguanidine (2.1 g, 0.025 mol) was dissolved in water (50 ml), and then a few drops of H~2~SO~4~ were added. The resulting mixture was refluxed for 2--3 h, and cooled to room temperature. The excess of ethanol was added, and then refluxed for 2--3 h. It was filtered through alumina. The filtrate was concentrated under reduced pressure and kept for crystallization. Recrystallization was carried out from ethanol/hexane (9:1) mixture in 5 d.

Figures
=======

![The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bonds are shown as dashed lines.](e-65-0o785-fig1){#Fap1}

![A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.](e-65-0o785-fig2){#Fap2}

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

  --------------------------------- -------------------------------------
  2C~4~H~10~N~3~O~2~^+^·SO~4~^2−^   *F*(000) = 760
  *M~r~* = 360.36                   *D*~x~ = 1.392 Mg m^−3^
  Monoclinic, *P*2~1~/*c*           Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc              Cell parameters from 25 reflections
  *a* = 9.3021 (12) Å               θ = 10.0--18.2°
  *b* = 11.0081 (11) Å              µ = 0.24 mm^−1^
  *c* = 17.1063 (13) Å              *T* = 296 K
  β = 100.980 (3)°                  Prism, colourless
  *V* = 1719.6 (3) Å^3^             0.24 × 0.18 × 0.15 mm
  *Z* = 4                           
  --------------------------------- -------------------------------------

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

  ------------------------------------------------------ --------------------------------------
  Enraf--Nonius CAD-4 diffractometer                     2124 reflections with *I* \> 2σ(*I*)
  Radiation source: fine-focus sealed tube               *R*~int~ = 0.025
  graphite                                               θ~max~ = 26.3°, θ~min~ = 2.2°
  ω/2θ scans                                             *h* = 0→11
  Absorption correction: ψ scan (North *et al.*, 1968)   *k* = 0→13
  *T*~min~ = 0.946, *T*~max~ = 0.967                     *l* = −21→20
  3481 measured reflections                              3 standard reflections every 120 min
  3481 independent reflections                           intensity decay: 1.7%
  ------------------------------------------------------ --------------------------------------

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

  ---------------------------------------------------------------- ----------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                                             Secondary atom site location: difference Fourier map
  Least-squares matrix: full                                       Hydrogen site location: inferred from neighbouring sites
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.045                              H atoms treated by a mixture of independent and constrained refinement
  *wR*(*F*^2^) = 0.108                                             *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0481*P*)^2^ + 0.1093*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.03                                                       (Δ/σ)~max~ \< 0.001
  3481 reflections                                                 Δρ~max~ = 0.21 e Å^−3^
  233 parameters                                                   Δρ~min~ = −0.25 e Å^−3^
  0 restraints                                                     Extinction correction: *SHELXL97* (Sheldrick, 2008), Fc^\*^=kFc\[1+0.001xFc^2^λ^3^/sin(2θ)\]^-1/4^
  Primary atom site location: structure-invariant direct methods   Extinction coefficient: 0.0037 (9)
  ---------------------------------------------------------------- ----------------------------------------------------------------------------------------------------

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

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. Bond distances, angles *etc*. have been calculated using the rounded fractional coordinates. All su\'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.\'s are taken into account in the estimation of distances, angles and torsion angles
  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^ \> σ(*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~   
  S1    0.74538 (6)    0.22561 (5)    0.25630 (4)     0.0324 (2)           
  O1    0.87642 (18)   0.15672 (16)   0.29258 (11)    0.0494 (6)           
  O2    0.78056 (17)   0.35534 (15)   0.25361 (10)    0.0398 (6)           
  O3    0.6301 (2)     0.20989 (17)   0.30259 (11)    0.0536 (7)           
  O4    0.6925 (2)     0.18149 (16)   0.17468 (10)    0.0492 (7)           
  O5    0.43306 (19)   0.28294 (17)   0.43071 (11)    0.0499 (6)           
  O6    0.53979 (17)   0.45797 (16)   0.40549 (11)    0.0471 (6)           
  O7    0.2706 (2)     0.42933 (17)   −0.03291 (11)   0.0560 (7)           
  O8    0.17269 (19)   0.60725 (16)   −0.00697 (10)   0.0460 (6)           
  N1    0.0671 (3)     0.4461 (2)     0.29228 (14)    0.0499 (8)           
  N2    0.1472 (3)     0.2719 (2)     0.35872 (15)    0.0529 (9)           
  N3    0.3058 (2)     0.43420 (19)   0.35471 (12)    0.0422 (7)           
  N4    0.5287 (3)     0.4909 (2)     0.19080 (14)    0.0500 (8)           
  N5    0.4929 (3)     0.3569 (2)     0.08613 (14)    0.0480 (8)           
  N6    0.3530 (2)     0.53306 (19)   0.08234 (12)    0.0426 (7)           
  C1    0.1711 (3)     0.3811 (2)     0.33493 (15)    0.0382 (8)           
  C2    0.4290 (3)     0.3811 (2)     0.40006 (15)    0.0381 (8)           
  C3    0.6785 (3)     0.4149 (3)     0.45146 (17)    0.0532 (10)          
  C4    0.7871 (3)     0.5128 (3)     0.4471 (2)      0.0807 (15)          
  C5    0.4611 (3)     0.4578 (2)     0.11953 (15)    0.0376 (8)           
  C6    0.2642 (3)     0.5151 (3)     0.00936 (15)    0.0387 (8)           
  C7    0.0712 (3)     0.6005 (3)     −0.08355 (15)   0.0502 (10)          
  C8    −0.0188 (4)    0.7126 (3)     −0.0906 (2)     0.0738 (12)          
  H1A   0.090 (3)      0.518 (3)      0.2665 (16)     0.0599\*             
  H1B   −0.020 (3)     0.421 (3)      0.2797 (17)     0.0599\*             
  H2A   0.215 (3)      0.234 (3)      0.3859 (18)     0.0634\*             
  H2B   0.059 (3)      0.237 (3)      0.3410 (17)     0.0634\*             
  H3A   0.70789        0.34004        0.42905         0.0638\*             
  H3B   0.67011        0.40013        0.50630         0.0638\*             
  H4A   0.88070        0.48943        0.47744         0.0965\*             
  H4B   0.75542        0.58660        0.46846         0.0965\*             
  H4C   0.79518        0.52545        0.39258         0.0965\*             
  H4D   0.499 (3)      0.563 (3)      0.2083 (16)     0.0600\*             
  H4E   0.608 (3)      0.445 (3)      0.2123 (16)     0.0600\*             
  H5    0.31494        0.50670        0.33757         0.0505\*             
  H5A   0.446 (3)      0.337 (3)      0.0435 (17)     0.0576\*             
  H5B   0.560 (3)      0.303 (3)      0.1145 (16)     0.0576\*             
  H6    0.33899        0.59866        0.10715         0.0511\*             
  H7A   0.00927        0.52921        −0.08540        0.0602\*             
  H7B   0.12481        0.59560        −0.12684        0.0602\*             
  H8A   −0.09353       0.70817        −0.13771        0.0883\*             
  H8B   0.04250        0.78183        −0.09397        0.0883\*             
  H8C   −0.06354       0.72035        −0.04471        0.0883\*             
  ----- -------------- -------------- --------------- -------------------- --

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

  ---- ------------- ------------- ------------- -------------- -------------- --------------
       *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  S1   0.0322 (3)    0.0241 (3)    0.0383 (4)    −0.0023 (3)    −0.0001 (3)    0.0012 (3)
  O1   0.0432 (11)   0.0334 (10)   0.0616 (12)   0.0064 (9)     −0.0152 (9)    −0.0021 (9)
  O2   0.0347 (9)    0.0263 (9)    0.0566 (11)   −0.0042 (7)    0.0041 (8)     0.0042 (8)
  O3   0.0547 (12)   0.0461 (12)   0.0647 (12)   −0.0088 (10)   0.0234 (10)    0.0106 (10)
  O4   0.0594 (12)   0.0378 (11)   0.0425 (11)   0.0086 (9)     −0.0106 (9)    −0.0060 (8)
  O5   0.0432 (10)   0.0396 (11)   0.0625 (12)   −0.0056 (9)    −0.0011 (9)    0.0182 (10)
  O6   0.0315 (9)    0.0409 (11)   0.0639 (12)   −0.0073 (8)    −0.0032 (8)    0.0060 (9)
  O7   0.0609 (12)   0.0462 (12)   0.0535 (12)   0.0160 (10)    −0.0080 (9)    −0.0187 (10)
  O8   0.0512 (11)   0.0440 (11)   0.0394 (10)   0.0178 (9)     0.0002 (8)     −0.0017 (9)
  N1   0.0359 (12)   0.0444 (15)   0.0620 (16)   −0.0101 (12)   −0.0097 (12)   0.0166 (12)
  N2   0.0430 (14)   0.0397 (15)   0.0673 (16)   −0.0156 (12)   −0.0113 (12)   0.0165 (12)
  N3   0.0344 (11)   0.0336 (13)   0.0537 (13)   −0.0085 (10)   −0.0036 (10)   0.0124 (10)
  N4   0.0540 (15)   0.0426 (15)   0.0466 (14)   0.0216 (12)    −0.0074 (11)   −0.0097 (12)
  N5   0.0548 (15)   0.0379 (14)   0.0451 (14)   0.0159 (12)    −0.0062 (11)   −0.0088 (12)
  N6   0.0498 (13)   0.0340 (12)   0.0408 (12)   0.0139 (11)    0.0006 (10)    −0.0078 (10)
  C1   0.0365 (14)   0.0356 (16)   0.0394 (14)   −0.0084 (12)   −0.0004 (11)   0.0031 (12)
  C2   0.0367 (14)   0.0365 (16)   0.0394 (14)   −0.0071 (12)   0.0033 (11)    0.0010 (12)
  C3   0.0355 (15)   0.0536 (19)   0.0644 (19)   −0.0006 (14)   −0.0058 (13)   −0.0074 (15)
  C4   0.0395 (17)   0.093 (3)     0.105 (3)     −0.0204 (18)   0.0024 (17)    −0.012 (2)
  C5   0.0391 (14)   0.0342 (15)   0.0388 (15)   0.0066 (12)    0.0055 (12)    −0.0001 (12)
  C6   0.0396 (14)   0.0345 (15)   0.0417 (15)   0.0051 (12)    0.0069 (12)    −0.0004 (13)
  C7   0.0500 (16)   0.0579 (19)   0.0384 (15)   0.0098 (15)    −0.0022 (12)   0.0020 (14)
  C8   0.070 (2)     0.075 (2)     0.070 (2)     0.032 (2)      −0.0028 (17)   0.0115 (19)
  ---- ------------- ------------- ------------- -------------- -------------- --------------

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

  ------------------- ------------- ------------------- ------------
  S1---O3             1.460 (2)     N5---C5             1.308 (3)
  S1---O4             1.4716 (18)   N6---C5             1.363 (3)
  S1---O1             1.4690 (19)   N6---C6             1.374 (3)
  S1---O2             1.4678 (17)   N4---H4E            0.91 (3)
  O5---C2             1.199 (3)     N4---H4D            0.91 (3)
  O6---C3             1.457 (3)     N5---H5B            0.93 (3)
  O6---C2             1.323 (3)     N5---H5A            0.81 (3)
  O7---C6             1.198 (4)     N6---H6             0.8600
  O8---C6             1.320 (4)     C3---C4             1.489 (4)
  O8---C7             1.464 (3)     C3---H3A            0.9700
  N1---C1             1.308 (4)     C3---H3B            0.9700
  N2---C1             1.302 (3)     C4---H4C            0.9600
  N3---C2             1.385 (3)     C4---H4B            0.9600
  N3---C1             1.366 (3)     C4---H4A            0.9600
  N1---H1A            0.95 (3)      C7---C8             1.483 (5)
  N1---H1B            0.84 (3)      C7---H7A            0.9700
  N2---H2A            0.82 (3)      C7---H7B            0.9700
  N2---H2B            0.90 (3)      C8---H8B            0.9600
  N3---H5             0.8600        C8---H8C            0.9600
  N4---C5             1.312 (3)     C8---H8A            0.9600
                                                        
  S1···H2B^i^         3.00 (3)      N4···O2             2.813 (3)
  S1···H4E            2.77 (3)      N5···O4             2.898 (3)
  S1···H5B            2.83 (3)      N5···O7             2.730 (3)
  S1···H1A^ii^        2.82 (3)      N5···C6^v^          3.341 (4)
  S1···H4D^ii^        3.04 (3)      N5···O5^iv^         3.031 (3)
  S1···H5^ii^         2.8900        N6···O3^vii^        2.752 (3)
  S1···H6^ii^         2.9500        C2···O3             3.320 (3)
  S1···H1B^i^         3.04 (3)      C3···O3             3.368 (4)
  O1···N2^i^          2.854 (3)     C5···O3^vii^        3.260 (3)
  O1···N1^ii^         2.837 (3)     C5···O7^v^          3.373 (3)
  O2···N1^i^          2.805 (3)     C6···N5^v^          3.341 (4)
  O2···N4             2.813 (3)     C2···H4B^viii^      3.1000
  O3···C2             3.320 (3)     C2···H2A            2.54 (3)
  O3···N4^ii^         2.841 (3)     C6···H5A            2.58 (3)
  O3···C5^ii^         3.260 (3)     H1A···S1^vii^       2.82 (3)
  O3···C3             3.368 (4)     H1A···O1^vii^       1.89 (3)
  O3···O5             3.216 (3)     H1A···H5            2.2100
  O3···N6^ii^         2.752 (3)     H1A···O4^vii^       2.75 (3)
  O4···N5             2.898 (3)     H1B···S1^vi^        3.04 (3)
  O4···N3^ii^         2.769 (3)     H1B···H2B           2.33 (5)
  O5···O7^iii^        2.914 (3)     H1B···O2^vi^        1.96 (3)
  O5···O3             3.216 (3)     H2A···O7^iii^       2.27 (3)
  O5···N2             2.712 (3)     H2A···C2            2.54 (3)
  O5···N5^iii^        3.031 (3)     H2A···O5            2.10 (3)
  O7···O5^iv^         2.914 (3)     H2B···O1^vi^        1.95 (3)
  O7···N5             2.730 (3)     H2B···H1B           2.33 (5)
  O7···N2^iv^         2.975 (3)     H2B···S1^vi^        3.00 (3)
  O7···C5^v^          3.373 (3)     H3A···O5            2.6400
  O1···H2B^i^         1.95 (3)      H3A···O3            2.5800
  O1···H1A^ii^        1.89 (3)      H3B···O5            2.6700
  O2···H1B^i^         1.96 (3)      H4A···H4A^ix^       2.2200
  O2···H5B            2.89 (3)      H4B···C2^viii^      3.1000
  O2···H4E            1.90 (3)      H4D···S1^vii^       3.04 (3)
  O2···H7B^v^         2.5500        H4D···H6            2.0900
  O3···H3A            2.5800        H4D···O3^vii^       2.00 (3)
  O3···H4D^ii^        2.00 (3)      H4E···S1            2.77 (3)
  O3···H6^ii^         1.9500        H4E···H5B           2.27 (4)
  O4···H5B            1.97 (3)      H4E···O2            1.90 (3)
  O4···H1A^ii^        2.75 (3)      H5···H1A            2.2100
  O4···H5^ii^         1.9400        H5···S1^vii^        2.8900
  O5···H3A            2.6400        H5···O4^vii^        1.9400
  O5···H3B            2.6700        H5A···C6            2.58 (3)
  O5···H5A^iii^       2.32 (3)      H5A···O5^iv^        2.32 (3)
  O5···H2A            2.10 (3)      H5A···O7            2.14 (3)
  O7···H7B            2.6300        H5B···O2            2.89 (3)
  O7···H7A            2.6600        H5B···O4            1.97 (3)
  O7···H5A            2.14 (3)      H5B···S1            2.83 (3)
  O7···H2A^iv^        2.27 (3)      H5B···H4E           2.27 (4)
  N1···O2^vi^         2.805 (3)     H6···S1^vii^        2.9500
  N1···O1^vii^        2.837 (3)     H6···O3^vii^        1.9500
  N2···O1^vi^         2.854 (3)     H6···H4D            2.0900
  N2···O5             2.712 (3)     H7A···O7            2.6600
  N2···O7^iii^        2.975 (3)     H7B···O7            2.6300
  N3···O4^vii^        2.769 (3)     H7B···O2^v^         2.5500
  N4···O3^vii^        2.841 (3)                         
                                                        
  O3---S1---O4        109.16 (11)   O5---C2---N3        125.4 (2)
  O1---S1---O3        110.23 (11)   O6---C3---C4        106.1 (2)
  O1---S1---O4        109.33 (11)   H3A---C3---H3B      109.00
  O1---S1---O2        110.09 (10)   O6---C3---H3B       111.00
  O2---S1---O4        109.12 (10)   O6---C3---H3A       111.00
  O2---S1---O3        108.88 (10)   C4---C3---H3A       111.00
  C2---O6---C3        115.3 (2)     C4---C3---H3B       111.00
  C6---O8---C7        115.5 (2)     C3---C4---H4C       109.00
  C1---N3---C2        125.5 (2)     H4A---C4---H4B      109.00
  C1---N1---H1A       120.5 (17)    H4A---C4---H4C      109.00
  C1---N1---H1B       122 (2)       C3---C4---H4A       109.00
  H1A---N1---H1B      116 (3)       C3---C4---H4B       109.00
  C1---N2---H2A       119 (2)       H4B---C4---H4C      109.00
  C1---N2---H2B       119 (2)       N4---C5---N5        122.2 (2)
  H2A---N2---H2B      122 (3)       N4---C5---N6        116.4 (2)
  C2---N3---H5        117.00        N5---C5---N6        121.3 (2)
  C1---N3---H5        117.00        O7---C6---N6        124.9 (3)
  C5---N6---C6        126.8 (2)     O7---C6---O8        125.6 (2)
  C5---N4---H4E       115.4 (18)    O8---C6---N6        109.5 (2)
  H4D---N4---H4E      129 (3)       O8---C7---C8        106.8 (2)
  C5---N4---H4D       115.2 (17)    C8---C7---H7A       110.00
  C5---N5---H5B       120.0 (18)    C8---C7---H7B       110.00
  C5---N5---H5A       120 (2)       O8---C7---H7A       110.00
  H5A---N5---H5B      120 (3)       O8---C7---H7B       110.00
  C6---N6---H6        117.00        H7A---C7---H7B      109.00
  C5---N6---H6        117.00        H8B---C8---H8C      109.00
  N2---C1---N3        121.4 (2)     C7---C8---H8A       109.00
  N1---C1---N3        116.8 (2)     C7---C8---H8B       109.00
  N1---C1---N2        121.8 (3)     C7---C8---H8C       109.00
  O6---C2---N3        108.65 (19)   H8A---C8---H8B      109.00
  O5---C2---O6        125.9 (2)     H8A---C8---H8C      109.00
                                                        
  C3---O6---C2---O5   1.9 (4)       C2---N3---C1---N2   0.4 (4)
  C3---O6---C2---N3   −179.8 (2)    C1---N3---C2---O5   −3.0 (4)
  C2---O6---C3---C4   178.0 (2)     C1---N3---C2---O6   178.6 (2)
  C6---O8---C7---C8   −179.0 (2)    C6---N6---C5---N4   −177.4 (3)
  C7---O8---C6---O7   0.5 (4)       C6---N6---C5---N5   1.2 (4)
  C7---O8---C6---N6   179.8 (2)     C5---N6---C6---O7   −0.7 (4)
  C2---N3---C1---N1   179.2 (2)     C5---N6---C6---O8   180.0 (2)
  ------------------- ------------- ------------------- ------------

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

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

  -------------------- ---------- ---------- ----------- ---------------
  *D*---H···*A*        *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  N1---H1A···O1^vii^   0.95 (3)   1.89 (3)   2.837 (3)   175 (3)
  N1---H1B···O2^vi^    0.84 (3)   1.96 (3)   2.805 (3)   177 (3)
  N2---H2A···O5        0.82 (3)   2.10 (3)   2.712 (3)   131 (3)
  N2---H2A···O7^iii^   0.82 (3)   2.27 (3)   2.975 (3)   144 (3)
  N2---H2B···O1^vi^    0.90 (3)   1.95 (3)   2.854 (3)   174 (3)
  N4---H4D···O3^vii^   0.91 (3)   2.00 (3)   2.841 (3)   153 (2)
  N4---H4E···O2        0.91 (3)   1.90 (3)   2.813 (3)   176 (3)
  N3---H5···O4^vii^    0.86       1.94       2.769 (3)   163
  N5---H5A···O7        0.81 (3)   2.14 (3)   2.730 (3)   130 (3)
  N5---H5A···O5^iv^    0.81 (3)   2.32 (3)   3.031 (3)   147 (3)
  N5---H5B···O4        0.93 (3)   1.97 (3)   2.898 (3)   177 (3)
  N6---H6···O3^vii^    0.86       1.95       2.752 (3)   155
  C3---H3A···O3        0.97       2.58       3.368 (4)   138
  C7---H7B···O2^v^     0.97       2.55       3.483 (3)   162
  -------------------- ---------- ---------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*          *D*---H    H⋯*A*      *D*⋯*A*     *D*---H⋯*A*
  -------------------- ---------- ---------- ----------- -------------
  N1---H1*A*⋯O1^i^     0.95 (3)   1.89 (3)   2.837 (3)   175 (3)
  N1---H1*B*⋯O2^ii^    0.84 (3)   1.96 (3)   2.805 (3)   177 (3)
  N2---H2*A*⋯O5        0.82 (3)   2.10 (3)   2.712 (3)   131 (3)
  N2---H2*A*⋯O7^iii^   0.82 (3)   2.27 (3)   2.975 (3)   144 (3)
  N2---H2*B*⋯O1^ii^    0.90 (3)   1.95 (3)   2.854 (3)   174 (3)
  N4---H4*D*⋯O3^i^     0.91 (3)   2.00 (3)   2.841 (3)   153 (2)
  N4---H4*E*⋯O2        0.91 (3)   1.90 (3)   2.813 (3)   176 (3)
  N3---H5⋯O4^i^        0.86       1.94       2.769 (3)   163
  N5---H5*A*⋯O7        0.81 (3)   2.14 (3)   2.730 (3)   130 (3)
  N5---H5*A*⋯O5^iv^    0.81 (3)   2.32 (3)   3.031 (3)   147 (3)
  N5---H5*B*⋯O4        0.93 (3)   1.97 (3)   2.898 (3)   177 (3)
  N6---H6⋯O3^i^        0.86       1.95       2.752 (3)   155
  C3---H3*A*⋯O3        0.97       2.58       3.368 (4)   138
  C7---H7*B*⋯O2^v^     0.97       2.55       3.483 (3)   162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .
