3,4-Diamino-pyridinium 4-nitro-benzoate-4-nitro-benzoic acid (1/1).

In the title compound, C(5)H(8)N(3) (+)·C(7)H(4)NO(4) (-)·C(7)H(5)NO(4), the non-H atoms of the 3,4-diamino-pyridinium cation are coplanar, with a maximum deviation of 0.022 (1) Å. The carboxyl-ate and nitro groups of the 4-nitro-benzoate anion are twisted out of the attached ring planes by dihedral angles of 15.89 (8) and 10.20 (8)°, respectively. In the 4-nitro-benzoic acid mol-ecule, the carboxyl and nitro groups form dihedral angles of 18.25 (8) and 6.55 (8)°, respectively, with the benzene ring. In the crystal, the constituent units form two-dimensional networks parallel to (001) by O-H⋯O, N--H⋯O and C-H⋯O hydrogen bonds. Weak π-π inter-actions involving inversion-related 4-nitro-benzoic acid mol-ecules [centroid-centroid distance = 3.7325 (8) Å] and inversion-related 4-nitro-benzoate mol-ecules [centroid-centroid distance = 3.7124 (8) Å] are also observed.

Related literature

For general background to substituted pyridines, see: Pozharski et al. (1997 ▶); Katritzky et al. (1996 ▶); For related structures, see: Opozda et al. (2006 ▶); Rubin-Preminger & Englert (2007 ▶); Koleva et al. (2007 ▶, 2008 ▶); Fun & Balasubramani (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C5H8N3 +·C7H4NO4 −·C7H5NO4

M = 443.38

Triclinic,

a = 6.8073 (2) Å

b = 6.8087 (2) Å

c = 21.0171 (5) Å

α = 80.859 (1)°

β = 83.253 (1)°

γ = 78.549 (1)°

V = 938.88 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.56 × 0.20 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.934, T max = 0.979

27907 measured reflections

5435 independent reflections

4025 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.190

S = 1.05

5435 reflections

353 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.81 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027354/ci2849sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027354/ci2849Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C5H8N3+·C7H4NO4−·C7H5NO4	Z = 2
Mr = 443.38	F(000) = 460
Triclinic, P1	Dx = 1.568 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8073 (2) Å	Cell parameters from 7405 reflections
b = 6.8087 (2) Å	θ = 3.1–33.7°
c = 21.0171 (5) Å	µ = 0.13 mm−1
α = 80.859 (1)°	T = 100 K
β = 83.253 (1)°	Block, yellow
γ = 78.549 (1)°	0.56 × 0.20 × 0.17 mm
V = 938.88 (5) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5435 independent reflections
Radiation source: fine-focus sealed tube	4025 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 30.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.934, Tmax = 0.979	k = −9→9
27907 measured reflections	l = −29→28

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.1091P)2 + 0.3802P] where P = (Fo2 + 2Fc2)/3
5435 reflections	(Δ/σ)max = 0.001
353 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1A	1.39968 (18)	0.6458 (2)	0.56237 (6)	0.0292 (3)
O2A	1.1299 (2)	0.6247 (2)	0.62692 (6)	0.0282 (3)
O3A	0.84687 (17)	0.9461 (2)	0.30121 (6)	0.0235 (3)
O4A	0.56283 (19)	0.8966 (2)	0.36256 (7)	0.0342 (4)
C7A	0.7456 (2)	0.8934 (2)	0.35545 (8)	0.0193 (3)
C1A	0.8875 (2)	0.7614 (2)	0.52810 (8)	0.0175 (3)
C2A	0.7744 (2)	0.8188 (2)	0.47485 (8)	0.0178 (3)
C3A	0.8705 (2)	0.8287 (2)	0.41221 (7)	0.0160 (3)
C4A	1.0802 (2)	0.7779 (2)	0.40257 (8)	0.0173 (3)
C5A	1.1946 (2)	0.7216 (2)	0.45525 (7)	0.0166 (3)
C6A	1.0950 (2)	0.7158 (2)	0.51679 (7)	0.0155 (3)
N1A	1.2168 (2)	0.6579 (2)	0.57258 (7)	0.0186 (3)
O1B	0.08979 (19)	0.3360 (2)	−0.05503 (7)	0.0309 (3)
O2B	0.3609 (2)	0.3677 (2)	−0.11725 (6)	0.0285 (3)
O3B	0.64656 (17)	0.0180 (2)	0.20718 (6)	0.0239 (3)
H1O3	0.7184	0.0014	0.2370	0.036*
O4B	0.91654 (18)	0.1156 (2)	0.14870 (6)	0.0276 (3)
C7B	0.7393 (2)	0.0931 (2)	0.15458 (8)	0.0185 (3)
C1B	0.2910 (2)	0.2478 (2)	0.05366 (8)	0.0177 (3)
C2B	0.4051 (2)	0.1875 (2)	0.10658 (7)	0.0170 (3)
C3B	0.6149 (2)	0.1559 (2)	0.09760 (8)	0.0164 (3)
C4B	0.7116 (2)	0.1852 (2)	0.03518 (8)	0.0180 (3)
C5B	0.5997 (2)	0.2440 (2)	−0.01814 (8)	0.0177 (3)
C6B	0.3922 (2)	0.2731 (2)	−0.00739 (7)	0.0163 (3)
N1B	0.2727 (2)	0.3303 (2)	−0.06376 (7)	0.0188 (3)
N2	0.3773 (2)	0.7229 (2)	0.23610 (7)	0.0261 (3)
N3	−0.0247 (2)	0.4644 (3)	0.21167 (9)	0.0355 (4)
N4	0.2251 (2)	0.1578 (2)	0.28541 (7)	0.0254 (3)
C8	0.4928 (3)	0.5748 (3)	0.27289 (9)	0.0243 (4)
C9	0.4450 (3)	0.3893 (3)	0.28994 (9)	0.0242 (4)
C10	0.2719 (2)	0.3463 (3)	0.27034 (8)	0.0204 (3)
C11	0.1493 (2)	0.5011 (3)	0.23126 (8)	0.0229 (3)
C12	0.2073 (3)	0.6893 (3)	0.21562 (9)	0.0241 (4)
H1N3	−0.023 (4)	0.312 (4)	0.2071 (13)	0.048 (7)*
H2N3	−0.080 (4)	0.564 (4)	0.1805 (15)	0.060 (8)*
H1N2	0.431 (3)	0.851 (4)	0.2220 (12)	0.036 (6)*
H1N4	0.312 (3)	0.070 (3)	0.3102 (11)	0.028 (5)*
H2N4	0.098 (3)	0.146 (3)	0.2834 (11)	0.028 (6)*
H1A	0.820 (3)	0.765 (3)	0.5715 (11)	0.027 (5)*
H2A	0.630 (4)	0.852 (3)	0.4818 (11)	0.034 (6)*
H4A	1.145 (3)	0.772 (3)	0.3597 (11)	0.023 (5)*
H5A	1.333 (3)	0.687 (3)	0.4501 (11)	0.027 (5)*
H8A	0.599 (4)	0.613 (4)	0.2850 (14)	0.052 (8)*
H1B	0.150 (4)	0.265 (3)	0.0608 (11)	0.033 (6)*
H2B	0.340 (3)	0.173 (3)	0.1505 (11)	0.029 (6)*
H4B	0.857 (4)	0.163 (4)	0.0290 (12)	0.036 (6)*
H5B	0.668 (4)	0.250 (4)	−0.0633 (12)	0.036 (6)*
H9	0.524 (4)	0.285 (4)	0.3184 (12)	0.041 (7)*
H12	0.147 (3)	0.800 (4)	0.1914 (12)	0.034 (6)*

	U11	U22	U33	U12	U13	U23
O1A	0.0199 (6)	0.0440 (8)	0.0234 (7)	−0.0055 (5)	−0.0076 (5)	−0.0003 (6)
O2A	0.0303 (7)	0.0390 (7)	0.0133 (6)	−0.0033 (5)	−0.0016 (5)	−0.0015 (5)
O3A	0.0195 (6)	0.0354 (7)	0.0147 (6)	−0.0023 (5)	−0.0024 (4)	−0.0030 (5)
O4A	0.0216 (6)	0.0494 (8)	0.0304 (7)	−0.0152 (6)	−0.0123 (5)	0.0159 (6)
C7A	0.0211 (7)	0.0166 (7)	0.0216 (8)	−0.0049 (6)	−0.0082 (6)	−0.0007 (6)
C1A	0.0199 (7)	0.0178 (7)	0.0150 (7)	−0.0043 (5)	−0.0003 (6)	−0.0026 (5)
C2A	0.0156 (7)	0.0178 (7)	0.0201 (8)	−0.0033 (5)	−0.0021 (6)	−0.0022 (6)
C3A	0.0173 (7)	0.0151 (6)	0.0158 (7)	−0.0034 (5)	−0.0034 (5)	−0.0010 (5)
C4A	0.0194 (7)	0.0183 (7)	0.0140 (7)	−0.0032 (5)	−0.0020 (5)	−0.0018 (5)
C5A	0.0156 (7)	0.0186 (7)	0.0158 (7)	−0.0029 (5)	−0.0015 (5)	−0.0029 (5)
C6A	0.0178 (7)	0.0154 (6)	0.0138 (7)	−0.0029 (5)	−0.0043 (5)	−0.0017 (5)
N1A	0.0223 (7)	0.0190 (6)	0.0151 (6)	−0.0033 (5)	−0.0047 (5)	−0.0026 (5)
O1B	0.0201 (6)	0.0475 (8)	0.0244 (7)	−0.0067 (5)	−0.0078 (5)	0.0025 (6)
O2B	0.0286 (6)	0.0405 (7)	0.0124 (6)	0.0004 (5)	−0.0014 (5)	−0.0008 (5)
O3B	0.0206 (6)	0.0375 (7)	0.0136 (6)	−0.0041 (5)	−0.0057 (4)	−0.0020 (5)
O4B	0.0197 (6)	0.0396 (7)	0.0237 (6)	−0.0069 (5)	−0.0077 (5)	0.0014 (5)
C7B	0.0193 (7)	0.0195 (7)	0.0172 (7)	−0.0010 (6)	−0.0052 (6)	−0.0042 (6)
C1B	0.0146 (7)	0.0212 (7)	0.0179 (7)	−0.0024 (5)	−0.0019 (5)	−0.0050 (6)
C2B	0.0182 (7)	0.0206 (7)	0.0125 (7)	−0.0033 (5)	−0.0023 (5)	−0.0034 (5)
C3B	0.0173 (7)	0.0165 (7)	0.0158 (7)	−0.0025 (5)	−0.0038 (5)	−0.0028 (5)
C4B	0.0164 (7)	0.0206 (7)	0.0174 (7)	−0.0028 (5)	−0.0022 (5)	−0.0040 (6)
C5B	0.0199 (7)	0.0189 (7)	0.0143 (7)	−0.0040 (5)	−0.0011 (5)	−0.0025 (5)
C6B	0.0185 (7)	0.0170 (7)	0.0137 (7)	−0.0025 (5)	−0.0047 (5)	−0.0019 (5)
N1B	0.0214 (6)	0.0186 (6)	0.0161 (6)	−0.0015 (5)	−0.0054 (5)	−0.0021 (5)
N2	0.0330 (8)	0.0230 (7)	0.0230 (8)	−0.0063 (6)	0.0024 (6)	−0.0071 (6)
N3	0.0229 (8)	0.0494 (11)	0.0333 (9)	−0.0102 (7)	−0.0129 (7)	0.0087 (8)
N4	0.0211 (7)	0.0290 (8)	0.0251 (8)	−0.0062 (6)	−0.0041 (6)	0.0025 (6)
C8	0.0315 (9)	0.0230 (8)	0.0215 (8)	−0.0065 (7)	−0.0059 (7)	−0.0080 (6)
C9	0.0279 (8)	0.0240 (8)	0.0204 (8)	−0.0003 (7)	−0.0063 (6)	−0.0049 (6)
C10	0.0203 (7)	0.0244 (8)	0.0156 (7)	−0.0019 (6)	0.0019 (6)	−0.0057 (6)
C11	0.0168 (7)	0.0332 (9)	0.0177 (8)	−0.0018 (6)	0.0002 (6)	−0.0048 (6)
C12	0.0248 (8)	0.0243 (8)	0.0202 (8)	0.0018 (6)	0.0007 (6)	−0.0036 (6)

O1A—N1A	1.2269 (18)	C2B—C3B	1.396 (2)
O2A—N1A	1.2317 (18)	C2B—H2B	0.98 (2)
O3A—C7A	1.299 (2)	C3B—C4B	1.400 (2)
O4A—C7A	1.232 (2)	C4B—C5B	1.390 (2)
C7A—C3A	1.504 (2)	C4B—H4B	0.97 (2)
C1A—C6A	1.386 (2)	C5B—C6B	1.384 (2)
C1A—C2A	1.393 (2)	C5B—H5B	1.00 (2)
C1A—H1A	0.97 (2)	C6B—N1B	1.473 (2)
C2A—C3A	1.397 (2)	N2—C8	1.347 (2)
C2A—H2A	0.96 (2)	N2—C12	1.353 (2)
C3A—C4A	1.399 (2)	N2—H1N2	1.00 (2)
C4A—C5A	1.389 (2)	N3—C11	1.379 (2)
C4A—H4A	0.96 (2)	N3—H1N3	1.05 (3)
C5A—C6A	1.386 (2)	N3—H2N3	0.92 (3)
C5A—H5A	0.92 (2)	N4—C10	1.364 (2)
C6A—N1A	1.4727 (19)	N4—H1N4	0.90 (2)
O1B—N1B	1.2307 (18)	N4—H2N4	0.89 (2)
O2B—N1B	1.2247 (18)	C8—C9	1.349 (2)
O3B—C7B	1.2913 (19)	C8—H8A	0.89 (3)
O3B—H1O3	0.82	C9—C10	1.390 (2)
O4B—C7B	1.2355 (19)	C9—H9	0.97 (2)
C7B—C3B	1.505 (2)	C10—C11	1.421 (2)
C1B—C6B	1.386 (2)	C11—C12	1.394 (3)
C1B—C2B	1.393 (2)	C12—H12	0.89 (2)
C1B—H1B	0.94 (2)
O4A—C7A—O3A	125.20 (15)	C5B—C4B—C3B	120.32 (14)
O4A—C7A—C3A	120.56 (15)	C5B—C4B—H4B	119.7 (14)
O3A—C7A—C3A	114.22 (13)	C3B—C4B—H4B	120.0 (14)
C6A—C1A—C2A	118.09 (14)	C6B—C5B—C4B	118.05 (14)
C6A—C1A—H1A	122.4 (13)	C6B—C5B—H5B	121.0 (14)
C2A—C1A—H1A	119.3 (13)	C4B—C5B—H5B	120.6 (14)
C1A—C2A—C3A	120.10 (14)	C5B—C6B—C1B	123.32 (14)
C1A—C2A—H2A	119.2 (14)	C5B—C6B—N1B	118.39 (14)
C3A—C2A—H2A	120.7 (14)	C1B—C6B—N1B	118.28 (13)
C2A—C3A—C4A	120.26 (14)	O2B—N1B—O1B	123.15 (14)
C2A—C3A—C7A	119.19 (14)	O2B—N1B—C6B	118.26 (13)
C4A—C3A—C7A	120.55 (14)	O1B—N1B—C6B	118.58 (13)
C5A—C4A—C3A	120.19 (14)	C8—N2—C12	120.32 (15)
C5A—C4A—H4A	119.4 (12)	C8—N2—H1N2	116.5 (14)
C3A—C4A—H4A	120.3 (12)	C12—N2—H1N2	122.9 (14)
C6A—C5A—C4A	118.16 (14)	C11—N3—H1N3	114.8 (14)
C6A—C5A—H5A	120.1 (14)	C11—N3—H2N3	112.8 (18)
C4A—C5A—H5A	121.7 (14)	H1N3—N3—H2N3	119 (2)
C1A—C6A—C5A	123.18 (14)	C10—N4—H1N4	113.8 (14)
C1A—C6A—N1A	118.74 (13)	C10—N4—H2N4	117.7 (14)
C5A—C6A—N1A	118.08 (13)	H1N4—N4—H2N4	124 (2)
O1A—N1A—O2A	123.50 (14)	N2—C8—C9	121.67 (17)
O1A—N1A—C6A	118.07 (13)	N2—C8—H8A	113.6 (18)
O2A—N1A—C6A	118.43 (13)	C9—C8—H8A	124.7 (18)
C7B—O3B—H1O3	109.5	C8—C9—C10	120.49 (16)
O4B—C7B—O3B	125.03 (14)	C8—C9—H9	121.6 (14)
O4B—C7B—C3B	119.89 (14)	C10—C9—H9	117.7 (14)
O3B—C7B—C3B	115.08 (13)	N4—C10—C9	121.17 (15)
C6B—C1B—C2B	117.96 (14)	N4—C10—C11	120.42 (16)
C6B—C1B—H1B	123.3 (15)	C9—C10—C11	118.34 (16)
C2B—C1B—H1B	118.7 (15)	N3—C11—C12	121.98 (16)
C1B—C2B—C3B	120.33 (14)	N3—C11—C10	119.85 (16)
C1B—C2B—H2B	120.5 (13)	C12—C11—C10	118.13 (16)
C3B—C2B—H2B	119.1 (13)	N2—C12—C11	121.03 (16)
C2B—C3B—C4B	120.01 (14)	N2—C12—H12	110.3 (14)
C2B—C3B—C7B	120.67 (14)	C11—C12—H12	128.6 (15)
C4B—C3B—C7B	119.31 (13)
C6A—C1A—C2A—C3A	0.1 (2)	O3B—C7B—C3B—C4B	−162.32 (14)
C1A—C2A—C3A—C4A	1.0 (2)	C2B—C3B—C4B—C5B	−0.6 (2)
C1A—C2A—C3A—C7A	−179.27 (14)	C7B—C3B—C4B—C5B	−179.72 (14)
O4A—C7A—C3A—C2A	−15.2 (2)	C3B—C4B—C5B—C6B	0.3 (2)
O3A—C7A—C3A—C2A	163.72 (14)	C4B—C5B—C6B—C1B	0.4 (2)
O4A—C7A—C3A—C4A	164.48 (16)	C4B—C5B—C6B—N1B	−178.44 (13)
O3A—C7A—C3A—C4A	−16.6 (2)	C2B—C1B—C6B—C5B	−0.8 (2)
C2A—C3A—C4A—C5A	−1.4 (2)	C2B—C1B—C6B—N1B	178.02 (13)
C7A—C3A—C4A—C5A	178.91 (14)	C5B—C6B—N1B—O2B	−6.6 (2)
C3A—C4A—C5A—C6A	0.6 (2)	C1B—C6B—N1B—O2B	174.52 (14)
C2A—C1A—C6A—C5A	−1.0 (2)	C5B—C6B—N1B—O1B	172.62 (14)
C2A—C1A—C6A—N1A	179.05 (13)	C1B—C6B—N1B—O1B	−6.3 (2)
C4A—C5A—C6A—C1A	0.7 (2)	C12—N2—C8—C9	0.6 (3)
C4A—C5A—C6A—N1A	−179.40 (13)	N2—C8—C9—C10	−0.7 (3)
C1A—C6A—N1A—O1A	−169.88 (14)	C8—C9—C10—N4	177.85 (16)
C5A—C6A—N1A—O1A	10.2 (2)	C8—C9—C10—C11	1.0 (3)
C1A—C6A—N1A—O2A	10.0 (2)	N4—C10—C11—N3	4.0 (3)
C5A—C6A—N1A—O2A	−169.97 (14)	C9—C10—C11—N3	−179.15 (16)
C6B—C1B—C2B—C3B	0.5 (2)	N4—C10—C11—C12	−178.05 (16)
C1B—C2B—C3B—C4B	0.2 (2)	C9—C10—C11—C12	−1.2 (2)
C1B—C2B—C3B—C7B	179.27 (14)	C8—N2—C12—C11	−0.8 (3)
O4B—C7B—C3B—C2B	−161.34 (15)	N3—C11—C12—N2	179.05 (17)
O3B—C7B—C3B—C2B	18.6 (2)	C10—C11—C12—N2	1.1 (2)
O4B—C7B—C3B—C4B	17.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3B—H1O3···O3Ai	0.82	1.65	2.463 (2)	173
N3—H1N3···O4Bii	1.05 (3)	2.08 (3)	3.008 (3)	146 (2)
N3—H2N3···O2Biii	0.92 (3)	2.39 (3)	3.129 (2)	138 (2)
N2—H1N2···O3Biv	1.00 (2)	2.00 (2)	2.929 (2)	154 (2)
N4—H1N4···O4Ai	0.90 (2)	2.18 (2)	3.068 (2)	169 (2)
N4—H2N4···O3Av	0.89 (2)	2.35 (2)	3.152 (2)	150 (2)
C1B—H1B···O4Bii	0.94 (2)	2.52 (2)	3.231 (2)	133 (2)
C4B—H4B···O1Bvi	0.97 (2)	2.54 (2)	3.250 (2)	130 (2)
C12—H12···O4Bvii	0.89 (2)	2.50 (2)	3.376 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3B—H1O3⋯O3Ai	0.82	1.65	2.463 (2)	173
N3—H1N3⋯O4Bii	1.05 (3)	2.08 (3)	3.008 (3)	146 (2)
N3—H2N3⋯O2Biii	0.92 (3)	2.39 (3)	3.129 (2)	138 (2)
N2—H1N2⋯O3Biv	1.00 (2)	2.00 (2)	2.929 (2)	154 (2)
N4—H1N4⋯O4Ai	0.90 (2)	2.18 (2)	3.068 (2)	169 (2)
N4—H2N4⋯O3Av	0.89 (2)	2.35 (2)	3.152 (2)	150 (2)
C1B—H1B⋯O4Bii	0.94 (2)	2.52 (2)	3.231 (2)	133 (2)
C4B—H4B⋯O1Bvi	0.97 (2)	2.54 (2)	3.250 (2)	130 (2)
C12—H12⋯O4Bvii	0.89 (2)	2.50 (2)	3.376 (2)	165 (2)

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