3-Amino-benzonitrile-3,5-dinitro-benzoic acid (1/1).

The asymmetric unit of the title co-crystal, C(7)H(6)N(2)·C(7)H(4)N(2)O(6), contains two formula units of both components. The crystal structure is stabilized by inter-molecular O-H⋯O, N-H⋯O, N-H⋯N and C-H⋯O hydrogen bonds, generating a two-dimensional wave-like network. π-π stacking inter-actions [centroid-centroid distances = 3.702 (2), 3.660 (2)and 3.671 (2) Å] stabilize the crystal packing.

Related literature

For general background to hydrogen bonding, see: Desiraju (2002 ▶); Prins et al. (2001 ▶); Steiner (2002 ▶). For background to the applications of co-crystals, see: Bhatt & Desiraju (2008 ▶); Etter & Baures (1988 ▶); Gao et al. (2004 ▶); Hori et al. (2009 ▶); Weyna et al. (2009 ▶). For the synthesis of co-crystals by complementary functional groups, see: Li et al. (2006 ▶); Roy et al. (2009 ▶); Wei (2007 ▶).

Experimental

Crystal data

C7H6N2·C7H4N2O6

M = 330.26

Triclinic,

a = 7.4547 (15) Å

b = 14.260 (3) Å

c = 14.845 (3) Å

α = 108.01 (3)°

β = 91.90 (3)°

γ = 93.37 (3)°

V = 1496.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.35 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.969, T max = 0.977

15550 measured reflections

6830 independent reflections

3195 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.159

S = 0.99

6830 reflections

461 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039870/kp2355sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039870/kp2355Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039870/kp2355Isup3.cml

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

C7H6N2·C7H4N2O6	Z = 4
Mr = 330.26	F(000) = 680
Triclinic, P1	Dx = 1.466 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4547 (15) Å	Cell parameters from 6830 reflections
b = 14.260 (3) Å	θ = 3.0–27.5°
c = 14.845 (3) Å	µ = 0.12 mm−1
α = 108.01 (3)°	T = 293 K
β = 91.90 (3)°	Block, colorless
γ = 93.37 (3)°	0.35 × 0.22 × 0.20 mm
V = 1496.0 (5) Å3

Bruker SMART CCD area-detector diffractometer	6830 independent reflections
Radiation source: fine-focus sealed tube	3195 reflections with I > 2σ(I)
graphite	Rint = 0.056
Detector resolution: 8.366 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −18→18
Tmin = 0.969, Tmax = 0.977	l = −19→19
15550 measured reflections

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0591P)2] where P = (Fo2 + 2Fc2)/3
6830 reflections	(Δ/σ)max < 0.001
461 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
C1	0.4080 (3)	0.01643 (18)	0.11993 (16)	0.0553 (6)
C2	0.3392 (3)	0.02905 (17)	0.21487 (15)	0.0490 (6)
C3	0.1637 (3)	−0.00114 (17)	0.22396 (15)	0.0490 (6)
H3A	0.0862	−0.0291	0.1707	0.059*
C4	0.1058 (3)	0.01088 (17)	0.31324 (16)	0.0506 (6)
C5	0.2159 (3)	0.05067 (18)	0.39350 (16)	0.0578 (6)
H5A	0.1751	0.0569	0.4534	0.069*
C6	0.3888 (3)	0.08091 (18)	0.38155 (16)	0.0544 (6)
C7	0.4516 (3)	0.07230 (17)	0.29418 (16)	0.0555 (6)
H7A	0.5686	0.0953	0.2884	0.067*
O1	0.3036 (2)	−0.03099 (14)	0.04900 (12)	0.0726 (6)
H1A	0.363 (5)	−0.035 (3)	−0.025 (3)	0.160 (14)*
O2	0.5615 (2)	0.05235 (14)	0.11410 (11)	0.0736 (5)
N1	−0.0818 (3)	−0.01956 (18)	0.32279 (18)	0.0721 (6)
O3	−0.1815 (2)	−0.04676 (16)	0.25263 (16)	0.0915 (7)
O4	−0.1288 (3)	−0.0171 (2)	0.40020 (16)	0.1302 (10)
N2	0.5102 (3)	0.12590 (18)	0.46559 (15)	0.0768 (7)
O5	0.4669 (3)	0.11480 (19)	0.53961 (14)	0.1112 (8)
O6	0.6490 (3)	0.16961 (19)	0.45609 (15)	0.1188 (9)
C8	0.3501 (3)	0.50842 (18)	0.10190 (17)	0.0544 (6)
C9	0.2362 (3)	0.50677 (16)	0.18160 (15)	0.0488 (6)
C10	0.0604 (3)	0.46720 (17)	0.16271 (16)	0.0536 (6)
H10A	0.0117	0.4431	0.1007	0.064*
C11	−0.0412 (3)	0.46423 (18)	0.23756 (17)	0.0527 (6)
C12	0.0242 (3)	0.49980 (17)	0.33016 (16)	0.0544 (6)
H12A	−0.0470	0.4979	0.3800	0.065*
C13	0.1991 (3)	0.53816 (17)	0.34579 (15)	0.0527 (6)
C14	0.3074 (3)	0.54240 (17)	0.27369 (16)	0.0517 (6)
H14A	0.4260	0.5687	0.2868	0.062*
N3	−0.2260 (3)	0.41929 (18)	0.21744 (18)	0.0714 (6)
O7	0.2803 (2)	0.47150 (15)	0.01875 (13)	0.0800 (6)
H9A	0.379 (6)	0.469 (3)	−0.047 (3)	0.203 (18)*
O8	0.5087 (2)	0.54478 (14)	0.12114 (12)	0.0714 (5)
O9	−0.2761 (2)	0.37659 (17)	0.13605 (16)	0.0941 (7)
O10	−0.3199 (2)	0.42753 (18)	0.28450 (15)	0.1015 (7)
O11	0.1742 (3)	0.58417 (17)	0.50753 (13)	0.1032 (7)
O12	0.4324 (3)	0.6007 (2)	0.45542 (14)	0.1205 (9)
N4	0.2750 (3)	0.57692 (17)	0.44339 (15)	0.0744 (6)
N5	0.3740 (4)	0.2057 (2)	−0.0240 (2)	0.1150 (10)
C15	0.2997 (4)	0.2144 (2)	0.0436 (2)	0.0796 (9)
C16	0.2076 (3)	0.22522 (19)	0.12900 (18)	0.0599 (7)
C17	0.0298 (4)	0.1905 (2)	0.1228 (2)	0.0735 (8)
H17A	−0.0302	0.1603	0.0641	0.088*
C18	−0.0566 (4)	0.2014 (2)	0.2050 (2)	0.0765 (8)
H18A	−0.180 (4)	0.1780 (19)	0.2036 (17)	0.086 (9)*
C19	0.0298 (4)	0.24544 (19)	0.2909 (2)	0.0685 (7)
H19A	−0.0323	0.2521	0.3456	0.082*
C20	0.2079 (3)	0.28052 (17)	0.29893 (18)	0.0596 (7)
C21	0.2961 (3)	0.27005 (18)	0.21579 (18)	0.0610 (7)
H21A	0.4159	0.2936	0.2189	0.073*
N6	0.2934 (5)	0.3273 (2)	0.3859 (2)	0.0891 (8)
H6A	0.240 (5)	0.317 (3)	0.437 (3)	0.127 (14)*
H6B	0.410 (4)	0.341 (2)	0.378 (2)	0.109 (13)*
N7	−0.1478 (4)	0.7302 (2)	0.4340 (2)	0.1190 (11)
C22	−0.0799 (4)	0.7346 (2)	0.3675 (2)	0.0822 (9)
C23	0.0139 (3)	0.73855 (18)	0.28564 (19)	0.0606 (7)
C24	−0.0753 (4)	0.7084 (2)	0.1977 (2)	0.0732 (8)
H24A	−0.1966	0.6869	0.1906	0.088*
C25	0.0187 (4)	0.7110 (2)	0.1210 (2)	0.0771 (8)
H25A	−0.0403	0.6921	0.0613	0.093*
C26	0.1980 (4)	0.74096 (19)	0.13031 (18)	0.0664 (7)
H26A	0.2596	0.7403	0.0767	0.080*
C27	0.2891 (3)	0.77223 (18)	0.21843 (18)	0.0584 (6)
C28	0.1939 (3)	0.76999 (17)	0.29630 (17)	0.0588 (6)
H28A	0.2519	0.7899	0.3563	0.071*
N8	0.4678 (4)	0.8027 (2)	0.2284 (3)	0.0883 (8)
H8A	0.524 (4)	0.806 (2)	0.176 (2)	0.103 (12)*
H8B	0.517 (5)	0.825 (3)	0.284 (3)	0.126 (15)*

	U11	U22	U33	U12	U13	U23
C1	0.0514 (14)	0.0662 (17)	0.0432 (14)	−0.0022 (12)	0.0060 (12)	0.0104 (13)
C2	0.0527 (14)	0.0535 (15)	0.0398 (13)	0.0060 (11)	0.0078 (11)	0.0119 (11)
C3	0.0552 (14)	0.0509 (14)	0.0424 (13)	0.0036 (11)	0.0047 (10)	0.0165 (11)
C4	0.0527 (13)	0.0536 (15)	0.0512 (15)	0.0053 (11)	0.0119 (11)	0.0233 (12)
C5	0.0707 (17)	0.0647 (17)	0.0426 (14)	0.0115 (13)	0.0127 (12)	0.0215 (13)
C6	0.0657 (15)	0.0574 (16)	0.0389 (13)	0.0058 (12)	0.0027 (11)	0.0129 (12)
C7	0.0528 (14)	0.0614 (16)	0.0509 (15)	0.0007 (12)	0.0048 (12)	0.0158 (13)
O1	0.0636 (10)	0.1044 (15)	0.0372 (10)	−0.0161 (10)	0.0058 (8)	0.0072 (10)
O2	0.0595 (11)	0.1067 (15)	0.0433 (10)	−0.0163 (10)	0.0104 (8)	0.0101 (10)
N1	0.0651 (15)	0.0872 (17)	0.0704 (17)	−0.0002 (12)	0.0185 (13)	0.0335 (14)
O3	0.0583 (11)	0.1231 (18)	0.0878 (15)	−0.0115 (11)	0.0058 (11)	0.0283 (14)
O4	0.0954 (16)	0.225 (3)	0.0855 (16)	−0.0204 (16)	0.0314 (13)	0.0746 (18)
N2	0.0839 (17)	0.0953 (19)	0.0439 (14)	−0.0009 (14)	−0.0024 (12)	0.0128 (13)
O5	0.1111 (17)	0.174 (2)	0.0451 (12)	−0.0154 (15)	−0.0068 (11)	0.0355 (14)
O6	0.1040 (17)	0.166 (2)	0.0704 (14)	−0.0510 (17)	−0.0168 (12)	0.0260 (15)
C8	0.0540 (15)	0.0601 (16)	0.0460 (15)	0.0010 (12)	0.0094 (12)	0.0121 (12)
C9	0.0539 (14)	0.0493 (14)	0.0433 (13)	0.0032 (11)	0.0108 (11)	0.0140 (11)
C10	0.0548 (14)	0.0584 (16)	0.0475 (14)	0.0034 (12)	0.0030 (11)	0.0163 (12)
C11	0.0449 (13)	0.0606 (16)	0.0584 (16)	0.0046 (11)	0.0109 (11)	0.0260 (13)
C12	0.0607 (15)	0.0575 (16)	0.0506 (15)	0.0067 (12)	0.0184 (12)	0.0231 (13)
C13	0.0616 (15)	0.0559 (15)	0.0408 (14)	−0.0003 (12)	0.0070 (11)	0.0157 (12)
C14	0.0508 (13)	0.0543 (15)	0.0487 (14)	−0.0002 (11)	0.0077 (11)	0.0143 (12)
N3	0.0505 (13)	0.0916 (18)	0.0756 (17)	0.0002 (12)	0.0066 (13)	0.0320 (15)
O7	0.0728 (12)	0.1110 (16)	0.0450 (11)	−0.0172 (10)	0.0127 (9)	0.0115 (11)
O8	0.0577 (11)	0.0959 (14)	0.0535 (11)	−0.0099 (10)	0.0156 (8)	0.0143 (10)
O9	0.0639 (12)	0.1283 (19)	0.0836 (15)	−0.0143 (11)	−0.0095 (11)	0.0288 (14)
O10	0.0590 (12)	0.158 (2)	0.0921 (16)	−0.0105 (12)	0.0214 (11)	0.0475 (15)
O11	0.1285 (17)	0.132 (2)	0.0450 (11)	−0.0182 (14)	0.0226 (12)	0.0245 (12)
O12	0.0902 (15)	0.187 (3)	0.0614 (13)	−0.0423 (16)	−0.0114 (11)	0.0159 (14)
N4	0.0881 (17)	0.0858 (18)	0.0440 (13)	−0.0099 (14)	0.0041 (13)	0.0154 (12)
N5	0.121 (2)	0.157 (3)	0.080 (2)	0.017 (2)	0.0235 (18)	0.053 (2)
C15	0.085 (2)	0.091 (2)	0.070 (2)	0.0088 (17)	0.0048 (17)	0.0367 (19)
C16	0.0650 (16)	0.0612 (17)	0.0546 (16)	0.0017 (13)	0.0008 (13)	0.0205 (14)
C17	0.0744 (18)	0.0696 (19)	0.0684 (19)	−0.0075 (15)	−0.0126 (15)	0.0137 (15)
C18	0.0634 (18)	0.075 (2)	0.087 (2)	−0.0125 (15)	0.0020 (17)	0.0222 (18)
C19	0.0726 (18)	0.0608 (18)	0.0721 (19)	0.0004 (14)	0.0124 (15)	0.0207 (15)
C20	0.0746 (17)	0.0462 (15)	0.0561 (17)	0.0016 (13)	−0.0079 (13)	0.0148 (13)
C21	0.0554 (14)	0.0606 (17)	0.0694 (18)	−0.0029 (12)	−0.0033 (13)	0.0258 (14)
N6	0.107 (2)	0.093 (2)	0.0613 (18)	−0.0088 (18)	−0.0128 (17)	0.0202 (15)
N7	0.146 (3)	0.112 (3)	0.107 (2)	0.0211 (19)	0.064 (2)	0.039 (2)
C22	0.091 (2)	0.071 (2)	0.087 (2)	0.0170 (16)	0.0310 (18)	0.0229 (18)
C23	0.0673 (16)	0.0535 (16)	0.0616 (17)	0.0104 (13)	0.0117 (14)	0.0168 (13)
C24	0.0606 (16)	0.0712 (19)	0.083 (2)	0.0050 (14)	−0.0036 (15)	0.0177 (17)
C25	0.090 (2)	0.076 (2)	0.0602 (18)	0.0097 (16)	−0.0166 (16)	0.0141 (16)
C26	0.0819 (19)	0.0663 (18)	0.0503 (16)	0.0071 (15)	0.0052 (14)	0.0169 (14)
C27	0.0653 (16)	0.0498 (15)	0.0593 (17)	0.0047 (12)	0.0038 (13)	0.0156 (13)
C28	0.0711 (17)	0.0541 (16)	0.0477 (15)	0.0046 (13)	−0.0056 (12)	0.0117 (13)
N8	0.0720 (18)	0.102 (2)	0.084 (2)	−0.0103 (15)	0.0072 (17)	0.0221 (19)

C1—O2	1.243 (3)	N3—O10	1.216 (3)
C1—O1	1.271 (3)	O7—H9A	1.23 (5)
C1—C2	1.478 (3)	O11—N4	1.216 (3)
C2—C7	1.376 (3)	O12—N4	1.194 (3)
C2—C3	1.377 (3)	N5—C15	1.139 (3)
C3—C4	1.371 (3)	C15—C16	1.433 (4)
C3—H3A	0.9300	C16—C21	1.374 (3)
C4—C5	1.370 (3)	C16—C17	1.377 (3)
C4—N1	1.464 (3)	C17—C18	1.370 (4)
C5—C6	1.369 (3)	C17—H17A	0.9300
C5—H5A	0.9300	C18—C19	1.356 (4)
C6—C7	1.366 (3)	C18—H18A	0.96 (3)
C6—N2	1.466 (3)	C19—C20	1.379 (3)
C7—H7A	0.9300	C19—H19A	0.9300
O1—H1A	1.18 (4)	C20—N6	1.371 (3)
N1—O4	1.203 (3)	C20—C21	1.389 (3)
N1—O3	1.206 (3)	C21—H21A	0.9300
N2—O5	1.209 (3)	N6—H6A	0.92 (3)
N2—O6	1.211 (3)	N6—H6B	0.90 (3)
C8—O8	1.250 (3)	N7—C22	1.140 (3)
C8—O7	1.263 (3)	C22—C23	1.437 (4)
C8—C9	1.484 (3)	C23—C24	1.376 (4)
C9—C14	1.378 (3)	C23—C28	1.377 (3)
C9—C10	1.380 (3)	C24—C25	1.365 (4)
C10—C11	1.375 (3)	C24—H24A	0.9300
C10—H10A	0.9300	C25—C26	1.369 (4)
C11—C12	1.371 (3)	C25—H25A	0.9300
C11—N3	1.466 (3)	C26—C27	1.384 (3)
C12—C13	1.368 (3)	C26—H26A	0.9300
C12—H12A	0.9300	C27—N8	1.365 (3)
C13—C14	1.376 (3)	C27—C28	1.384 (3)
C13—N4	1.462 (3)	C28—H28A	0.9300
C14—H14A	0.9300	N8—H8A	0.91 (3)
N3—O9	1.208 (3)	N8—H8B	0.85 (3)
O2—C1—O1	124.3 (2)	O9—N3—C11	118.6 (2)
O2—C1—C2	118.9 (2)	O10—N3—C11	117.5 (2)
O1—C1—C2	116.8 (2)	C8—O7—H9A	116.9 (18)
C7—C2—C3	120.3 (2)	O12—N4—O11	123.8 (2)
C7—C2—C1	119.4 (2)	O12—N4—C13	118.0 (2)
C3—C2—C1	120.3 (2)	O11—N4—C13	118.3 (2)
C4—C3—C2	118.5 (2)	N5—C15—C16	179.5 (3)
C4—C3—H3A	120.8	C21—C16—C17	120.7 (2)
C2—C3—H3A	120.8	C21—C16—C15	120.2 (2)
C5—C4—C3	122.7 (2)	C17—C16—C15	119.1 (3)
C5—C4—N1	119.0 (2)	C18—C17—C16	118.5 (3)
C3—C4—N1	118.4 (2)	C18—C17—H17A	120.7
C6—C5—C4	117.1 (2)	C16—C17—H17A	120.7
C6—C5—H5A	121.5	C19—C18—C17	121.1 (3)
C4—C5—H5A	121.5	C19—C18—H18A	118.0 (15)
C7—C6—C5	122.4 (2)	C17—C18—H18A	120.9 (15)
C7—C6—N2	118.6 (2)	C18—C19—C20	121.4 (3)
C5—C6—N2	118.9 (2)	C18—C19—H19A	119.3
C6—C7—C2	119.0 (2)	C20—C19—H19A	119.3
C6—C7—H7A	120.5	N6—C20—C19	121.1 (3)
C2—C7—H7A	120.5	N6—C20—C21	121.1 (3)
C1—O1—H1A	113.5 (16)	C19—C20—C21	117.7 (2)
O4—N1—O3	123.0 (2)	C16—C21—C20	120.5 (2)
O4—N1—C4	118.5 (3)	C16—C21—H21A	119.7
O3—N1—C4	118.5 (2)	C20—C21—H21A	119.7
O5—N2—O6	124.3 (2)	C20—N6—H6A	116 (2)
O5—N2—C6	117.6 (2)	C20—N6—H6B	109 (2)
O6—N2—C6	118.1 (2)	H6A—N6—H6B	129 (3)
O8—C8—O7	124.3 (2)	N7—C22—C23	177.1 (4)
O8—C8—C9	118.2 (2)	C24—C23—C28	121.0 (2)
O7—C8—C9	117.5 (2)	C24—C23—C22	119.8 (3)
C14—C9—C10	120.4 (2)	C28—C23—C22	119.2 (3)
C14—C9—C8	120.0 (2)	C25—C24—C23	118.4 (3)
C10—C9—C8	119.6 (2)	C25—C24—H24A	120.8
C11—C10—C9	118.6 (2)	C23—C24—H24A	120.8
C11—C10—H10A	120.7	C24—C25—C26	121.3 (3)
C9—C10—H10A	120.7	C24—C25—H25A	119.3
C12—C11—C10	122.8 (2)	C26—C25—H25A	119.3
C12—C11—N3	118.6 (2)	C25—C26—C27	120.9 (3)
C10—C11—N3	118.6 (2)	C25—C26—H26A	119.5
C13—C12—C11	116.8 (2)	C27—C26—H26A	119.5
C13—C12—H12A	121.6	N8—C27—C26	121.3 (3)
C11—C12—H12A	121.6	N8—C27—C28	120.8 (3)
C12—C13—C14	122.9 (2)	C26—C27—C28	117.8 (2)
C12—C13—N4	118.8 (2)	C23—C28—C27	120.6 (2)
C14—C13—N4	118.2 (2)	C23—C28—H28A	119.7
C13—C14—C9	118.5 (2)	C27—C28—H28A	119.7
C13—C14—H14A	120.7	C27—N8—H8A	118 (2)
C9—C14—H14A	120.7	C27—N8—H8B	118 (2)
O9—N3—O10	123.9 (2)	H8A—N8—H8B	123 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2i	1.18 (4)	1.41 (4)	2.590 (2)	173 (3)
N6—H6A···N7ii	0.92 (3)	2.32 (4)	3.232 (5)	169 (3)
N6—H6B···O12iii	0.90 (3)	2.57 (3)	2.953 (4)	107 (2)
N8—H8A···N5iv	0.91 (3)	2.37 (3)	3.262 (5)	170 (3)
N8—H8B···O5iii	0.85 (3)	2.48 (4)	3.286 (4)	157 (3)
O7—H9A···O8iv	1.23 (5)	1.38 (5)	2.608 (2)	174 (4)
C5—H5A···O4v	0.93	2.44	3.321 (3)	158.
C12—H12A···O11ii	0.93	2.50	3.352 (3)	153.
C18—H18A···O2vi	0.96 (3)	2.58 (3)	3.421 (4)	147 (2)
C21—H21A···O10vii	0.93	2.60	3.451 (3)	153.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	1.18 (4)	1.41 (4)	2.590 (2)	173 (3)
N6—H6A⋯N7ii	0.92 (3)	2.32 (4)	3.232 (5)	169 (3)
N6—H6B⋯O12iii	0.90 (3)	2.57 (3)	2.953 (4)	107 (2)
N8—H8A⋯N5iv	0.91 (3)	2.37 (3)	3.262 (5)	170 (3)
N8—H8B⋯O5iii	0.85 (3)	2.48 (4)	3.286 (4)	157 (3)
O7—H9A⋯O8iv	1.23 (5)	1.38 (5)	2.608 (2)	174 (4)
C5—H5A⋯O4v	0.93	2.44	3.321 (3)	158
C12—H12A⋯O11ii	0.93	2.50	3.352 (3)	153
C18—H18A⋯O2vi	0.96 (3)	2.58 (3)	3.421 (4)	147 (2)
C21—H21A⋯O10vii	0.93	2.60	3.451 (3)	153

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