R-free factor and experimental charge-density analysis of 1-(2′-aminophenyl)-2-methyl-4-nitroimidazole: a crystal structure with Z′ = 2

The experimental charge-density distribution was determined for 1-(2′-aminophenyl)-2-methyl-4-nitro-1H-imidazole crystals. An anharmonic model was applied to the N atoms of both amino groups and to one nitro group in order to account for high residual peaks after harmonic multipole refinement and to obtain a better charge-density model. Free R-factor calculations [Brünger (1992). Nature, 355, 472–475] with restrained models implemented in MoPro were used to determine the degree of similarity of the two symmetry-independent molecules in the unit cell. The results are compared with 1-phenyl-4-nitroimidazole in order to analyze the influence of the amine and methyl functional groups. The asymmetric unit contains two symmetry-independent molecules giving rise to a dimer connected via strong N—H...N hydrogen bonds; these dimers are the building blocks of the crystal. In the crystal structure there are also weaker interactions and many short directional contacts (C—H...O, C—H...N and C—H...π), for which the Koch–Popelier topological criteria were applied. This analysis revealed that the C—H...π interactions lie at the border between weak hydrogen bonds and van der Waals interactions. Special attention was also paid to stabilizing H...H interactions. It turned out that the electron density, Laplacian and density energies at the critical points show an exponential dependence on the contact distance, similar to the relation found for other interactions.

Computing details

Program(s) used to refine structure: MoPro (J. Appl. Cryst. 2005, 38, 38-54).

(I)

Crystal data

C10H10N4O2	F(000) = 912
Mr = 218.22	Dx = 1.409 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 34615 reflections
a = 11.0299 (2) Å	θ = 2.9–55.4°
b = 10.0921 (2) Å	µ = 0.10 mm^−1
c = 18.6365 (3) Å	T = 100 K
β = 97.238 (2)°	Cube, yellow
V = 2057.99 (6) Å^3	0.35 × 0.35 × 0.35 mm
Z = 8

Data collection

Xcalibur, Eos diffractometer	15247 independent reflections
Radiation source: fine-focus sealed tube	15219 reflections with > 2.0σ(I)
Graphite monochromator	θmax = 51.4°, θmin = 2.9°
ω scan	h = −24→24
Absorption correction: analytical CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.36d (release 24-03-2009 CrysAlis171 .NET) (compiled Mar 24 2009,17:36:51) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)	k = 0→22
Tmin = 0.974, Tmax = 0.979	l = 0→40
26440 measured reflections

Refinement

Refinement on F	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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.025	H-atom parameters constrained
S = 1.07	w = 1/[1.101*σ^2(Fo^2)]
15247 reflections	(Δ/σ)max = 0.004
288 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.20139 (3)	0.47967 (3)	0.05249 (1)	0.01334 (1)
C2	0.14946 (3)	0.35848 (3)	0.06743 (2)	0.01927 (2)
H2	0.14528	0.33355	0.12359	0.03152
C3	0.10427 (3)	0.27362 (3)	0.01158 (2)	0.02121 (2)
H3	0.06449	0.17886	0.02268	0.03526
C4	0.11304 (3)	0.31204 (3)	−0.05958 (2)	0.01825 (2)
H4	0.08243	0.24609	−0.10403	0.03791
C5	0.16344 (3)	0.43319 (3)	−0.07478 (2)	0.01742 (2)
H5	0.16909	0.46328	−0.13004	0.03649
C6	0.20865 (3)	0.52098 (3)	−0.01885 (1)	0.01444 (1)
N6	0.26254 (3)	0.63837 (3)	−0.03415 (1)	0.02266 (2)
H61	0.27147	0.71232	0.00257	0.02824
H62	0.25461	0.66565	−0.08662	0.03143
N1	0.25181 (2)	0.56179 (2)	0.11193 (1)	0.01246 (1)
C9	0.18793 (3)	0.63551 (3)	0.15614 (1)	0.01373 (1)
H9	0.08926	0.64362	0.14762	0.03018
C8	0.27628 (3)	0.68677 (3)	0.20690 (1)	0.01267 (1)
N8	0.25623 (3)	0.76810 (3)	0.26677 (1)	0.01716 (1)
O81	0.15021 (3)	0.80081 (3)	0.27255 (2)	0.02539 (2)
O82	0.34427 (3)	0.80103 (3)	0.30988 (2)	0.02840 (2)
N2	0.39124 (2)	0.64800 (2)	0.19607 (1)	0.01319 (1)
C7	0.37399 (3)	0.57153 (3)	0.13828 (1)	0.01286 (1)
H71	0.55693	0.53485	0.12839	0.03578
H72	0.46365	0.39669	0.11787	0.03759
H73	0.45870	0.51307	0.04919	0.03607
C71	0.47019 (3)	0.49884 (4)	0.10595 (2)	0.02044 (2)
C1A	0.67116 (2)	0.94115 (3)	0.15119 (1)	0.01222 (1)
C2A	0.74248 (3)	1.02703 (3)	0.11566 (2)	0.01590 (1)
H2A	0.69744	1.08332	0.07048	0.03088
C3A	0.86753 (3)	1.03518 (3)	0.13700 (2)	0.01825 (2)
H3A	0.92312	1.10130	0.10906	0.03401
C4A	0.91980 (3)	0.95470 (3)	0.19360 (2)	0.01646 (2)
H4A	1.01727	0.95897	0.21070	0.03507
C5A	0.84894 (3)	0.86728 (3)	0.22785 (2)	0.01496 (1)
H5A	0.89055	0.80145	0.26981	0.03377
C6A	0.72162 (2)	0.85922 (3)	0.20808 (1)	0.01325 (1)
N6A	0.65079 (3)	0.77623 (3)	0.24388 (2)	0.02222 (2)
H61A	0.56334	0.75654	0.22388	0.02755
H62A	0.69413	0.70259	0.27345	0.03009
N1A	0.54298 (2)	0.93187 (2)	0.12634 (1)	0.01224 (1)
C9A	0.44946 (2)	0.98788 (3)	0.15771 (1)	0.01320 (1)
H9A	0.46773	1.04570	0.20684	0.03021
C8A	0.34629 (2)	0.94994 (3)	0.11330 (1)	0.01246 (1)
N8A	0.22278 (2)	0.98466 (3)	0.12049 (1)	0.01509 (1)
O81A	0.20503 (2)	1.06008 (3)	0.17046 (2)	0.02372 (2)
O82A	0.14069 (2)	0.93904 (3)	0.07728 (2)	0.02306 (2)
N2A	0.37220 (2)	0.87357 (2)	0.05688 (1)	0.01353 (1)
C7A	0.49258 (3)	0.86426 (3)	0.06557 (1)	0.01317 (1)
H71A	0.50547	0.74597	−0.02382	0.03679
H72A	0.62233	0.86182	−0.00848	0.03800
H73A	0.62494	0.72404	0.04490	0.03618
C71A	0.56653 (3)	0.79452 (3)	0.01612 (2)	0.01949 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.01619 (10)	0.01350 (9)	0.00990 (8)	−0.00211 (7)	−0.00009 (7)	−0.00102 (7)
C2	0.0252 (1)	0.0166 (1)	0.0155 (1)	−0.00664 (10)	0.00156 (9)	0.00012 (8)
H2	0.0398	0.0316	0.0225	0.0026	0.0025	−0.0058
C3	0.0254 (1)	0.0158 (1)	0.0217 (1)	−0.00639 (10)	−0.00004 (10)	−0.00242 (9)
H3	0.0428	0.0257	0.0363	−0.0006	0.0019	−0.0112
C4	0.0192 (1)	0.0163 (1)	0.0182 (1)	−0.00078 (9)	−0.00307 (9)	−0.00583 (8)
H4	0.0500	0.0333	0.0290	−0.0111	−0.0012	−0.0116
C5	0.0219 (1)	0.0179 (1)	0.01168 (9)	−0.00110 (9)	−0.00196 (8)	−0.00356 (8)
H5	0.0499	0.0393	0.0194	−0.0016	0.0019	−0.0101
C6	0.0190 (1)	0.01408 (9)	0.00964 (8)	−0.00201 (8)	−0.00065 (7)	−0.00104 (7)
N6	0.0371 (2)	0.0186 (1)	0.01171 (8)	−0.0094 (1)	0.00196 (9)	0.00028 (7)
H61	0.0370	0.0253	0.0216	−0.0045	0.0006	−0.0014
H62	0.0422	0.0337	0.0173	0.0020	−0.0004	−0.0036
N1	0.01335 (8)	0.01428 (8)	0.00939 (7)	−0.00069 (6)	0.00010 (6)	−0.00178 (6)
C9	0.01247 (9)	0.01621 (9)	0.01221 (8)	0.00041 (7)	0.00068 (7)	−0.00167 (7)
H9	0.0191	0.0375	0.0333	−0.0058	0.0017	0.0000
C8	0.01465 (9)	0.01308 (8)	0.01003 (8)	−0.000060 (7)	0.00118 (7)	−0.00135 (6)
N8	0.0229 (1)	0.01553 (9)	0.01297 (8)	0.00013 (8)	0.00400 (8)	−0.00325 (7)
O81	0.0286 (1)	0.0252 (1)	0.0225 (1)	0.00962 (10)	0.00728 (9)	−0.00393 (9)
O82	0.0300 (1)	0.0356 (1)	0.01920 (10)	−0.0084 (1)	0.00280 (9)	−0.01462 (10)
N2	0.01354 (8)	0.01570 (8)	0.00991 (7)	−0.00098 (7)	−0.00016 (6)	−0.00149 (6)
C7	0.01305 (9)	0.01540 (9)	0.00986 (8)	0.00060 (7)	0.00068 (7)	−0.00127 (7)
H71	0.0236	0.0401	0.0426	−0.0114	−0.0001	−0.0029
H72	0.0425	0.0210	0.0495	0.0032	0.0131	0.0017
H73	0.0417	0.0452	0.0208	0.0010	0.0045	0.0098
C71	0.0172 (1)	0.0266 (1)	0.0173 (1)	0.00521 (10)	0.00293 (9)	−0.00456 (10)
C1A	0.01077 (8)	0.01291 (8)	0.01261 (8)	−0.00051 (7)	0.000043 (7)	0.00082 (7)
C2A	0.01453 (10)	0.01590 (10)	0.01693 (10)	−0.00179 (8)	0.00129 (8)	0.00362 (8)
H2A	0.0281	0.0339	0.0294	0.0096	−0.0017	−0.0001
C3A	0.01409 (10)	0.0195 (1)	0.0210 (1)	−0.00354 (9)	0.00337 (9)	0.00238 (9)
H3A	0.0266	0.0377	0.0374	0.0086	0.0055	−0.0067
C4A	0.01108 (9)	0.0204 (1)	0.0176 (1)	−0.00180 (8)	0.00169 (8)	−0.00121 (8)
H4A	0.0188	0.0420	0.0430	0.0059	−0.0029	−0.0026
C5A	0.01087 (9)	0.0198 (1)	0.01379 (9)	0.00021 (8)	−0.00018 (7)	0.00063 (8)
H5A	0.0278	0.0366	0.0353	0.0115	−0.0049	0.0014
C6A	0.01062 (8)	0.01579 (9)	0.01301 (8)	−0.00049 (7)	0.00030 (7)	0.00212 (7)
N6A	0.01394 (9)	0.0274 (1)	0.0246 (1)	−0.00278 (9)	−0.00076 (8)	0.01325 (10)
H61A	0.0212	0.0317	0.0286	0.0010	−0.0032	−0.0029
H62A	0.0286	0.0297	0.0305	0.0074	−0.0043	0.0012
N1A	0.01083 (7)	0.01311 (7)	0.01232 (7)	0.00044 (6)	−0.00056 (6)	−0.00103 (6)
C9A	0.01189 (9)	0.01469 (9)	0.01260 (8)	−0.00038 (7)	−0.00016 (7)	−0.00226 (7)
H9A	0.0289	0.0333	0.0277	−0.0127	0.0013	−0.0008
C8A	0.01126 (8)	0.01238 (8)	0.01330 (8)	−0.00010 (7)	−0.00041 (7)	−0.00068 (7)
N8A	0.01157 (8)	0.01473 (8)	0.01857 (9)	−0.00089 (7)	0.00058 (7)	−0.00119 (7)
O81A	0.01442 (9)	0.0265 (1)	0.0303 (1)	−0.00247 (8)	0.00611 (8)	−0.01099 (9)
O82A	0.01229 (8)	0.0281 (1)	0.0277 (1)	−0.00057 (8)	−0.00337 (8)	−0.00608 (9)
N2A	0.01281 (8)	0.01337 (8)	0.01378 (8)	0.000056 (6)	−0.00174 (6)	−0.00146 (6)
C7A	0.01318 (9)	0.01268 (8)	0.01320 (8)	0.00109 (7)	−0.00019 (7)	−0.00162 (7)
H71A	0.0325	0.0480	0.0287	−0.0138	−0.0007	−0.0048
H72A	0.0407	0.0341	0.0403	0.0001	0.0186	−0.0090
H73A	0.0384	0.0399	0.0297	0.0043	0.0040	0.0147
C71A	0.0194 (1)	0.0192 (1)	0.0196 (1)	0.00247 (9)	0.00275 (9)	−0.00576 (9)

Geometric parameters (Å, º)

C1—N1	1.4379 (3)	C1A—N1A	1.4342 (3)
C1—C6	1.4053 (4)	C1A—C6A	1.4031 (4)
C1—C2	1.3934 (4)	C1A—C2A	1.3928 (4)
C2—C3	1.3908 (4)	C2A—C3A	1.3890 (4)
C2—H2	1.083	C2A—H2A	1.083
C3—C4	1.3966 (5)	C3A—C4A	1.3969 (4)
C3—H3	1.083	C3A—H3A	1.083
C4—C5	1.3870 (5)	C4A—C5A	1.3865 (4)
C4—H4	1.083	C4A—H4A	1.083
C5—C6	1.4104 (4)	C5A—C6A	1.4087 (4)
C5—H5	1.083	C5A—H5A	1.083
C6—N6	1.3714 (4)	C6A—N6A	1.3742 (4)
N6—H61	1.009	N6A—H61A	1.009
N6—H62	1.009	N6A—H62A	1.009
N1—C7	1.3785 (4)	N1A—C7A	1.3778 (3)
N1—C9	1.3694 (4)	N1A—C9A	1.3702 (4)
C9—C8	1.3709 (4)	C9A—C8A	1.3744 (4)
C9—H9	1.083	C9A—H9A	1.083
C8—N8	1.4247 (4)	C8A—N8A	1.4292 (4)
C8—N2	1.3661 (4)	C8A—N2A	1.3627 (4)
N8—O82	1.2256 (4)	N8A—O82A	1.2232 (3)
N8—O81	1.2328 (4)	N8A—O81A	1.2373 (4)
N2—C7	1.3190 (3)	N2A—C7A	1.3206 (4)
C7—C71	1.4793 (4)	C7A—C71A	1.4830 (4)
H71—C71	1.059	H71A—C71A	1.059
H72—C71	1.059	H72A—C71A	1.059
H73—C71	1.059	H73A—C71A	1.059
C1—N1—C7	125.55 (3)	C1A—N1A—C7A	125.23 (3)
C1—N1—C9	126.75 (2)	C1A—N1A—C9A	126.86 (3)
C1—C6—N6	122.06 (3)	C1A—C6A—N6A	122.03 (3)
C1—C6—C5	117.12 (3)	C1A—C6A—C5A	116.82 (2)
C1—C2—C3	120.57 (4)	C1A—C2A—C3A	120.05 (2)
C1—C2—H2	117.7	C1A—C2A—H2A	117.7
C2—C1—N1	118.74 (3)	C2A—C1A—N1A	118.69 (3)
C2—C1—C6	121.55 (3)	C2A—C1A—C6A	122.13 (3)
C2—C3—C4	118.58 (4)	C2A—C3A—C4A	118.83 (3)
C2—C3—H3	121.1	C2A—C3A—H3A	120.0
H2—C2—C3	121.7	H2A—C2A—C3A	122.2
C3—C4—C5	121.08 (3)	C3A—C4A—C5A	120.98 (3)
C3—C4—H4	120.2	C3A—C4A—H4A	119.9
H3—C3—C4	120.3	H3A—C3A—C4A	121.1
C4—C5—C6	121.08 (3)	C4A—C5A—C6A	121.16 (3)
C4—C5—H5	120.9	C4A—C5A—H5A	120.7
H4—C4—C5	118.7	H4A—C4A—C5A	119.1
C5—C6—N6	120.74 (3)	C5A—C6A—N6A	121.14 (3)
H5—C5—C6	118.0	H5A—C5A—C6A	118.1
C6—N6—H61	120.4	C6A—N6A—H61A	121.1
C6—N6—H62	116.8	C6A—N6A—H62A	117.1
C6—C1—N1	119.68 (2)	C6A—C1A—N1A	119.11 (3)
H61—N6—H62	116.4	H61A—N6A—H62A	114.9
N1—C7—N2	111.50 (2)	N1A—C7A—N2A	111.15 (3)
N1—C7—C71	122.59 (2)	N1A—C7A—C71A	123.31 (3)
N1—C9—C8	104.20 (2)	N1A—C9A—C8A	103.82 (3)
N1—C9—H9	122.4	N1A—C9A—H9A	120.9
C9—N1—C7	107.51 (2)	C9A—N1A—C7A	107.91 (2)
C9—C8—N8	126.21 (3)	C9A—C8A—N8A	127.01 (4)
C9—C8—N2	112.47 (2)	C9A—C8A—N2A	112.58 (3)
H9—C9—C8	133.4	H9A—C9A—C8A	135.3
C8—N8—O82	118.77 (3)	C8A—N8A—O82A	118.77 (3)
C8—N8—O81	117.73 (3)	C8A—N8A—O81A	117.67 (3)
C8—N2—C7	104.31 (2)	C8A—N2A—C7A	104.53 (2)
N8—C8—N2	121.28 (3)	N8A—C8A—N2A	120.40 (3)
O81—N8—O82	123.51 (3)	O81A—N8A—O82A	123.56 (4)
N2—C7—C71	125.85 (3)	N2A—C7A—C71A	125.51 (3)
C7—C71—H72	109.0	C7A—C71A—H73A	110.6
C7—C71—H71	109.1	C7A—C71A—H72A	111.1
C7—C71—H73	109.8	C7A—C71A—H71A	107.8
H71—C71—H72	109.5	H71A—C71A—H73A	109.7
H71—C71—H73	109.7	H71A—C71A—H72A	110.2
H72—C71—H73	109.8	H72A—C71A—H73A	107.5
C1—N1—C7—N2	−175.80 (2)	C1A—N1A—C7A—N2A	179.87 (2)
C1—N1—C7—C71	1.75 (3)	C1A—N1A—C7A—C71A	−1.89 (2)
C1—N1—C9—C8	175.51 (2)	C1A—N1A—C9A—C8A	179.83 (2)
C1—N1—C9—H9	−4.2	C1A—N1A—C9A—H9A	−0.7
C1—C6—N6—H61	−21.9	C1A—C6A—N6A—H61A	13.3
C1—C6—N6—H62	−172.7	C1A—C6A—N6A—H62A	162.7
C1—C6—C5—C4	0.61 (2)	C1A—C6A—C5A—C4A	1.55 (2)
C1—C6—C5—H5	−179.5	C1A—C6A—C5A—H5A	−177.0
C1—C2—C3—C4	0.54 (3)	C1A—C2A—C3A—C4A	0.92 (3)
C1—C2—C3—H3	179.4	C1A—C2A—C3A—H3A	179.4
C2—C1—N1—C7	99.67 (3)	C2A—C1A—N1A—C7A	76.61 (2)
C2—C1—N1—C9	−74.60 (2)	C2A—C1A—N1A—C9A	−103.08 (3)
C2—C1—C6—N6	−178.18 (3)	C2A—C1A—C6A—N6A	178.85 (3)
C2—C1—C6—C5	−1.32 (3)	C2A—C1A—C6A—C5A	−0.17 (2)
C2—C3—C4—C5	−1.24 (3)	C2A—C3A—C4A—C5A	0.44 (3)
C2—C3—C4—H4	177.2	C2A—C3A—C4A—H4A	179.4
H2—C2—C1—N1	3.0	H2A—C2A—C1A—N1A	0.0
H2—C2—C1—C6	−178.9	H2A—C2A—C1A—C6A	176.9
H2—C2—C3—C4	−179.8	H2A—C2A—C3A—C4A	−177.0
H2—C2—C3—H3	−0.9	H2A—C2A—C3A—H3A	1.6
C3—C2—C1—N1	−177.31 (3)	C3A—C2A—C1A—N1A	−178.00 (3)
C3—C2—C1—C6	0.76 (3)	C3A—C2A—C1A—C6A	−1.06 (3)
C3—C4—C5—C6	0.67 (3)	C3A—C4A—C5A—C6A	−1.72 (3)
C3—C4—C5—H5	−179.2	C3A—C4A—C5A—H5A	176.8
H3—C3—C4—C5	179.8	H3A—C3A—C4A—C5A	−178.1
H3—C3—C4—H4	−1.7	H3A—C3A—C4A—H4A	0.9
C4—C5—C6—N6	177.52 (3)	C4A—C5A—C6A—N6A	−177.49 (3)
H4—C4—C5—C6	−177.8	H4A—C4A—C5A—C6A	179.3
H4—C4—C5—H5	2.3	H4A—C4A—C5A—H5A	−2.2
C5—C6—N6—H61	161.4	C5A—C6A—N6A—H61A	−167.7
C5—C6—N6—H62	10.6	C5A—C6A—N6A—H62A	−18.3
C5—C6—C1—N1	176.74 (2)	C5A—C6A—C1A—N1A	176.75 (2)
H5—C5—C6—N6	−2.6	H5A—C5A—C6A—N6A	4.0
C6—C1—N1—C7	−78.44 (2)	C6A—C1A—N1A—C7A	−100.42 (2)
C6—C1—N1—C9	107.29 (3)	C6A—C1A—N1A—C9A	79.88 (2)
N6—C6—C1—N1	−0.12 (2)	N6A—C6A—C1A—N1A	−4.22 (2)
N1—C7—N2—C8	0.54 (2)	N1A—C7A—N2A—C8A	0.51 (2)
N1—C7—C71—H72	−71.0	N1A—C7A—C71A—H73A	56.4
N1—C7—C71—H71	169.5	N1A—C7A—C71A—H72A	−62.9
N1—C7—C71—H73	49.3	N1A—C7A—C71A—H71A	176.3
N1—C9—C8—N8	−178.07 (2)	N1A—C9A—C8A—N8A	−178.34 (2)
N1—C9—C8—N2	−0.08 (2)	N1A—C9A—C8A—N2A	0.23 (2)
C9—N1—C7—N2	−0.61 (2)	C9A—N1A—C7A—N2A	−0.39 (2)
C9—N1—C7—C71	176.94 (2)	C9A—N1A—C7A—C71A	177.85 (2)
C9—C8—N8—O82	176.29 (3)	C9A—C8A—N8A—O82A	−177.83 (3)
C9—C8—N8—O81	−3.19 (3)	C9A—C8A—N8A—O81A	2.32 (3)
C9—C8—N2—C7	−0.28 (2)	C9A—C8A—N2A—C7A	−0.46 (2)
H9—C9—N1—C7	−179.3	H9A—C9A—N1A—C7A	179.6
H9—C9—C8—N8	1.6	H9A—C9A—C8A—N8A	2.3
H9—C9—C8—N2	179.6	H9A—C9A—C8A—N2A	−179.2
C8—N2—C7—C71	−176.92 (2)	C8A—N2A—C7A—C71A	−177.69 (2)
C8—C9—N1—C7	0.40 (2)	C8A—C9A—N1A—C7A	0.09 (2)
N8—C8—N2—C7	177.82 (2)	N8A—C8A—N2A—C7A	178.22 (2)
O81—N8—C8—N2	178.98 (3)	O81A—N8A—C8A—N2A	−176.15 (3)
O82—N8—C8—N2	−1.54 (3)	O82A—N8A—C8A—N2A	3.70 (3)
N2—C7—C71—H72	106.2	N2A—C7A—C71A—H73A	−125.6
N2—C7—C71—H71	−13.3	N2A—C7A—C71A—H72A	115.1
N2—C7—C71—H73	−133.5	N2A—C7A—C71A—H71A	−5.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H61···N2A	1.01	2.15	3.0754 (4)	152
N6A—H61A···N2	1.01	2.20	3.1657 (4)	161
N6—H62···O82^i	1.01	2.30	3.2087 (4)	149
C71—H72···O82^ii	1.06	2.55	3.1345 (4)	114
N6A—H62A···O81A^ii	1.01	2.03	3.0325 (4)	175
C4A—H4A···O81^iii	1.08	2.37	3.1770 (4)	130
C4A—H4A···O81A^iii	1.08	2.51	3.3996 (4)	139
C9A—H9A···N2^iv	1.08	2.46	3.4522 (3)	152
C2A—H2A···N2A^v	1.08	2.44	3.4526 (4)	155

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