3,5-Bis(4-meth-oxy-phen-yl)-4H-1,2,4-triazol-4-amine.

The title compound, C(16)H(16)N(4)O(2), crystallizes with two mol-ecules in the asymmetric unit, which are related by a non-crystallographic centre of inversion. The phenyl-ene rings are twisted out of the mean plane of the triazole ring by 19.3 (1) and 21.4 (1)° for one independent mol-ecule and by 16.3 (1) and 18.1 (1)° for the other mol-ecule. In the crystal, adjacent mol-ecules are linked by amine-triazole N-H⋯N hydrogen bonds, forming chains running along the a axis.

Related literature

For the synthesis, see: Bentiss et al. (1999 ▶). For the two polymorphs of 3,5-diphenyl-1,2,4-triazol-4-amine, see: Ikemi et al. (2002 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C16H16N4O2

M = 296.33

Monoclinic,

a = 11.2232 (9) Å

b = 7.2386 (6) Å

c = 17.9766 (14) Å

β = 107.147 (1)°

V = 1395.51 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.40 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

12717 measured reflections

3459 independent reflections

2709 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.147

S = 1.06

3459 reflections

417 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030898/bt5318sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030898/bt5318Isup2.hkl

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

C16H16N4O2	F(000) = 624
Mr = 296.33	Dx = 1.410 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5135 reflections
a = 11.2232 (9) Å	θ = 2.4–28.0°
b = 7.2386 (6) Å	µ = 0.10 mm−1
c = 17.9766 (14) Å	T = 100 K
β = 107.147 (1)°	Block, colorless
V = 1395.51 (19) Å3	0.40 × 0.20 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	2709 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.086
graphite	θmax = 27.5°, θmin = 1.9°
ω scans	h = −13→14
12717 measured reflections	k = −8→9
3459 independent reflections	l = −23→23

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0797P)2 + 0.357P] where P = (Fo2 + 2Fc2)/3
3459 reflections	(Δ/σ)max = 0.001
417 parameters	Δρmax = 0.48 e Å−3
5 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.9153 (3)	0.5009 (5)	0.97018 (15)	0.0398 (8)
O2	0.3820 (2)	0.3666 (4)	0.22405 (14)	0.0290 (6)
O3	1.3936 (3)	−0.0328 (5)	0.95364 (14)	0.0361 (7)
O4	0.8588 (3)	0.1022 (4)	0.20680 (14)	0.0305 (6)
N1	0.7126 (3)	0.4643 (4)	0.58797 (17)	0.0204 (6)
H1	0.760 (3)	0.391 (5)	0.572 (2)	0.035 (12)*
H2	0.690 (4)	0.541 (5)	0.5496 (19)	0.047 (14)*
N2	0.6066 (3)	0.3855 (4)	0.60149 (16)	0.0195 (6)
N3	0.4738 (3)	0.3072 (5)	0.66424 (18)	0.0271 (7)
N4	0.4144 (3)	0.2941 (5)	0.58558 (18)	0.0250 (7)
N5	1.1929 (3)	0.0393 (5)	0.56489 (17)	0.0236 (7)
H3	1.250 (3)	0.124 (4)	0.5753 (19)	0.016 (9)*
H4	1.218 (4)	−0.062 (4)	0.590 (2)	0.048 (15)*
N6	1.0885 (3)	0.1032 (4)	0.58499 (16)	0.0188 (6)
N7	0.9526 (3)	0.1627 (4)	0.64705 (17)	0.0222 (7)
N8	0.8932 (3)	0.1714 (4)	0.56805 (16)	0.0214 (6)
C1	1.0453 (4)	0.5275 (8)	0.9815 (2)	0.0457 (12)
H1A	1.0859	0.5625	1.0358	0.069*
H1B	1.0573	0.6257	0.9469	0.069*
H1C	1.0821	0.4124	0.9697	0.069*
C2	0.8434 (4)	0.4603 (6)	0.8967 (2)	0.0297 (9)
C3	0.7162 (4)	0.4492 (6)	0.8863 (2)	0.0329 (9)
H3A	0.6851	0.4625	0.9298	0.039*
C4	0.6349 (4)	0.4191 (6)	0.8137 (2)	0.0300 (9)
H4A	0.5478	0.4138	0.8069	0.036*
C5	0.6804 (4)	0.3960 (5)	0.7490 (2)	0.0244 (8)
C6	0.8074 (4)	0.3992 (5)	0.7609 (2)	0.0253 (8)
H6	0.8392	0.3781	0.7182	0.030*
C7	0.8894 (4)	0.4322 (5)	0.8337 (2)	0.0281 (9)
H7	0.9767	0.4358	0.8406	0.034*
C8	0.5891 (3)	0.3635 (5)	0.6732 (2)	0.0215 (8)
C9	0.4956 (3)	0.3413 (5)	0.5486 (2)	0.0199 (7)
C10	0.4680 (3)	0.3512 (5)	0.4645 (2)	0.0203 (8)
C11	0.5510 (3)	0.2879 (5)	0.4247 (2)	0.0206 (7)
H11	0.6301	0.2400	0.4533	0.025*
C12	0.5189 (3)	0.2948 (5)	0.3459 (2)	0.0234 (8)
H12	0.5756	0.2500	0.3200	0.028*
C13	0.4049 (4)	0.3657 (5)	0.3023 (2)	0.0232 (8)
C14	0.3203 (3)	0.4288 (5)	0.3405 (2)	0.0235 (8)
H14	0.2412	0.4757	0.3115	0.028*
C15	0.3530 (3)	0.4220 (5)	0.4202 (2)	0.0219 (8)
H15	0.2961	0.4666	0.4461	0.026*
C16	0.2587 (4)	0.4115 (6)	0.1774 (2)	0.0342 (9)
H16A	0.2526	0.3960	0.1223	0.051*
H16B	0.2400	0.5399	0.1871	0.051*
H16C	0.1988	0.3293	0.1910	0.051*
C17	1.5222 (4)	−0.0665 (7)	0.9644 (2)	0.0410 (11)
H17A	1.5601	−0.1173	1.0166	0.062*
H17B	1.5637	0.0496	0.9589	0.062*
H17C	1.5314	−0.1551	0.9253	0.062*
C18	1.3227 (4)	0.0143 (5)	0.8802 (2)	0.0266 (8)
C19	1.1953 (4)	0.0294 (6)	0.8700 (2)	0.0272 (8)
H19	1.1632	0.0146	0.9130	0.033*
C20	1.1158 (4)	0.0662 (6)	0.7968 (2)	0.0266 (9)
H20	1.0287	0.0750	0.7900	0.032*
C21	1.1598 (3)	0.0907 (5)	0.73283 (19)	0.0204 (7)
C22	1.2876 (3)	0.0831 (5)	0.7455 (2)	0.0224 (8)
H22	1.3202	0.1051	0.7032	0.027*
C23	1.3697 (3)	0.0442 (6)	0.8186 (2)	0.0256 (8)
H23	1.4570	0.0383	0.8258	0.031*
C24	1.0701 (3)	0.1204 (5)	0.65715 (19)	0.0196 (7)
C25	0.9752 (3)	0.1338 (5)	0.53199 (19)	0.0203 (7)
C26	0.9471 (3)	0.1218 (5)	0.44711 (18)	0.0206 (7)
C27	1.0301 (3)	0.1839 (5)	0.4078 (2)	0.0227 (8)
H27	1.1091	0.2324	0.4362	0.027*
C28	0.9970 (3)	0.1744 (5)	0.3280 (2)	0.0224 (8)
H28	1.0538	0.2149	0.3013	0.027*
C29	0.8810 (3)	0.1060 (5)	0.2859 (2)	0.0229 (8)
C30	0.7986 (3)	0.0431 (5)	0.3239 (2)	0.0235 (8)
H30	0.7197	−0.0053	0.2953	0.028*
C31	0.8327 (3)	0.0519 (5)	0.4042 (2)	0.0223 (8)
H31	0.7762	0.0089	0.4306	0.027*
C32	0.7358 (4)	0.0492 (6)	0.1612 (2)	0.0339 (9)
H32A	0.7269	0.0688	0.1059	0.051*
H32B	0.6740	0.1241	0.1763	0.051*
H32C	0.7223	−0.0817	0.1702	0.051*

	U11	U22	U33	U12	U13	U23
O1	0.0458 (19)	0.0434 (19)	0.0300 (13)	0.0051 (16)	0.0107 (12)	−0.0016 (13)
O2	0.0240 (15)	0.0265 (15)	0.0349 (14)	0.0012 (12)	0.0061 (11)	−0.0008 (11)
O3	0.0378 (17)	0.0413 (18)	0.0283 (13)	−0.0032 (15)	0.0083 (12)	0.0034 (12)
O4	0.0288 (15)	0.0290 (15)	0.0321 (13)	−0.0016 (13)	0.0067 (11)	−0.0003 (12)
N1	0.0146 (14)	0.0163 (15)	0.0330 (15)	−0.0016 (13)	0.0115 (12)	0.0035 (12)
N2	0.0169 (15)	0.0122 (14)	0.0310 (14)	0.0003 (12)	0.0095 (12)	−0.0001 (11)
N3	0.0259 (17)	0.0195 (17)	0.0400 (17)	0.0034 (14)	0.0161 (14)	0.0045 (13)
N4	0.0193 (15)	0.0161 (15)	0.0420 (17)	0.0007 (13)	0.0129 (13)	0.0016 (12)
N5	0.0175 (16)	0.0187 (15)	0.0342 (16)	0.0003 (13)	0.0071 (13)	−0.0053 (13)
N6	0.0170 (14)	0.0119 (13)	0.0279 (14)	−0.0010 (12)	0.0072 (12)	−0.0005 (11)
N7	0.0174 (15)	0.0168 (15)	0.0349 (15)	0.0008 (13)	0.0117 (13)	−0.0029 (12)
N8	0.0212 (15)	0.0140 (14)	0.0320 (15)	0.0008 (12)	0.0128 (12)	−0.0001 (12)
C1	0.043 (3)	0.049 (3)	0.037 (2)	0.008 (2)	−0.0003 (19)	−0.003 (2)
C2	0.037 (2)	0.025 (2)	0.0283 (18)	0.0084 (19)	0.0109 (16)	0.0026 (15)
C3	0.043 (3)	0.030 (2)	0.0323 (19)	0.009 (2)	0.0218 (18)	0.0051 (16)
C4	0.030 (2)	0.025 (2)	0.041 (2)	0.0064 (17)	0.0205 (17)	0.0065 (16)
C5	0.030 (2)	0.0135 (17)	0.0315 (18)	0.0014 (16)	0.0116 (15)	0.0022 (14)
C6	0.027 (2)	0.0213 (19)	0.0315 (18)	0.0030 (17)	0.0139 (15)	−0.0002 (15)
C7	0.030 (2)	0.024 (2)	0.0325 (18)	0.0040 (17)	0.0126 (16)	0.0032 (15)
C8	0.0208 (18)	0.0112 (17)	0.0364 (19)	0.0009 (15)	0.0143 (15)	0.0032 (14)
C9	0.0110 (17)	0.0084 (16)	0.0411 (19)	0.0004 (13)	0.0087 (15)	−0.0014 (13)
C10	0.0124 (17)	0.0064 (16)	0.043 (2)	−0.0001 (13)	0.0100 (15)	−0.0018 (13)
C11	0.0109 (16)	0.0119 (17)	0.0392 (18)	−0.0009 (13)	0.0074 (14)	−0.0003 (14)
C12	0.0146 (17)	0.0164 (18)	0.0401 (19)	−0.0001 (14)	0.0093 (15)	−0.0012 (14)
C13	0.0207 (18)	0.0111 (16)	0.0369 (19)	−0.0018 (15)	0.0072 (15)	−0.0025 (14)
C14	0.0141 (17)	0.0119 (18)	0.043 (2)	0.0008 (14)	0.0071 (15)	0.0015 (14)
C15	0.0131 (17)	0.0086 (17)	0.046 (2)	0.0016 (14)	0.0112 (15)	−0.0031 (14)
C16	0.033 (2)	0.025 (2)	0.039 (2)	0.0030 (18)	0.0005 (17)	−0.0027 (16)
C17	0.033 (2)	0.044 (3)	0.040 (2)	−0.003 (2)	0.0010 (18)	0.0060 (19)
C18	0.030 (2)	0.0184 (19)	0.0311 (18)	−0.0020 (16)	0.0095 (15)	−0.0015 (14)
C19	0.031 (2)	0.028 (2)	0.0274 (17)	−0.0030 (18)	0.0165 (16)	−0.0002 (15)
C20	0.028 (2)	0.020 (2)	0.0357 (19)	−0.0008 (16)	0.0143 (16)	−0.0042 (14)
C21	0.0208 (18)	0.0141 (17)	0.0275 (16)	−0.0027 (15)	0.0089 (14)	−0.0025 (13)
C22	0.0226 (18)	0.0151 (18)	0.0323 (17)	−0.0042 (15)	0.0122 (15)	−0.0004 (13)
C23	0.0231 (19)	0.0211 (19)	0.0328 (18)	−0.0002 (16)	0.0086 (15)	−0.0013 (15)
C24	0.0184 (17)	0.0100 (16)	0.0336 (17)	−0.0021 (14)	0.0129 (14)	−0.0017 (13)
C25	0.0173 (17)	0.0122 (18)	0.0310 (17)	−0.0014 (14)	0.0067 (14)	0.0005 (13)
C26	0.0210 (18)	0.0126 (17)	0.0278 (16)	0.0065 (15)	0.0065 (14)	0.0007 (13)
C27	0.0171 (18)	0.0117 (17)	0.0383 (19)	0.0009 (14)	0.0066 (15)	−0.0001 (14)
C28	0.0206 (18)	0.0136 (17)	0.0365 (19)	0.0004 (15)	0.0140 (15)	0.0012 (14)
C29	0.0217 (18)	0.0137 (17)	0.0326 (17)	0.0046 (15)	0.0067 (15)	−0.0008 (14)
C30	0.0186 (18)	0.0157 (18)	0.0356 (18)	0.0011 (15)	0.0070 (14)	−0.0034 (14)
C31	0.0171 (17)	0.0157 (18)	0.0346 (18)	0.0027 (15)	0.0084 (15)	−0.0009 (14)
C32	0.035 (2)	0.028 (2)	0.0340 (19)	−0.0001 (19)	0.0028 (16)	0.0022 (16)

O1—C2	1.361 (4)	C10—C11	1.408 (5)
O1—C1	1.426 (5)	C11—C12	1.357 (5)
O2—C13	1.353 (4)	C11—H11	0.9500
O2—C16	1.428 (5)	C12—C13	1.386 (5)
O3—C18	1.368 (4)	C12—H12	0.9500
O3—C17	1.419 (5)	C13—C14	1.403 (5)
O4—C29	1.370 (4)	C14—C15	1.372 (5)
O4—C32	1.435 (5)	C14—H14	0.9500
N1—N2	1.404 (4)	C15—H15	0.9500
N1—H1	0.86 (4)	C16—H16A	0.9800
N1—H2	0.86 (3)	C16—H16B	0.9800
N2—C9	1.363 (4)	C16—H16C	0.9800
N2—C8	1.368 (4)	C17—H17A	0.9800
N3—C8	1.321 (5)	C17—H17B	0.9800
N3—N4	1.377 (4)	C17—H17C	0.9800
N4—C9	1.321 (5)	C18—C23	1.377 (5)
N5—N6	1.403 (4)	C18—C19	1.392 (5)
N5—H3	0.86 (3)	C19—C20	1.380 (5)
N5—H4	0.87 (3)	C19—H19	0.9500
N6—C25	1.363 (4)	C20—C21	1.391 (5)
N6—C24	1.378 (4)	C20—H20	0.9500
N7—C24	1.314 (5)	C21—C22	1.386 (5)
N7—N8	1.381 (4)	C21—C24	1.450 (5)
N8—C25	1.301 (5)	C22—C23	1.393 (5)
C1—H1A	0.9800	C22—H22	0.9500
C1—H1B	0.9800	C23—H23	0.9500
C1—H1C	0.9800	C25—C26	1.467 (4)
C2—C3	1.387 (6)	C26—C31	1.384 (5)
C2—C7	1.392 (5)	C26—C27	1.398 (5)
C3—C4	1.372 (6)	C27—C28	1.374 (5)
C3—H3A	0.9500	C27—H27	0.9500
C4—C5	1.411 (5)	C28—C29	1.390 (5)
C4—H4A	0.9500	C28—H28	0.9500
C5—C6	1.378 (5)	C29—C30	1.379 (5)
C5—C8	1.463 (5)	C30—C31	1.382 (5)
C6—C7	1.380 (5)	C30—H30	0.9500
C6—H6	0.9500	C31—H31	0.9500
C7—H7	0.9500	C32—H32A	0.9800
C9—C10	1.454 (5)	C32—H32B	0.9800
C10—C15	1.398 (5)	C32—H32C	0.9800
C2—O1—C1	117.1 (3)	C13—C14—H14	120.4
C13—O2—C16	117.7 (3)	C14—C15—C10	121.7 (3)
C18—O3—C17	117.0 (3)	C14—C15—H15	119.2
C29—O4—C32	116.6 (3)	C10—C15—H15	119.2
N2—N1—H1	116 (3)	O2—C16—H16A	109.5
N2—N1—H2	109 (3)	O2—C16—H16B	109.5
H1—N1—H2	101 (4)	H16A—C16—H16B	109.5
C9—N2—C8	105.9 (3)	O2—C16—H16C	109.5
C9—N2—N1	128.4 (3)	H16A—C16—H16C	109.5
C8—N2—N1	125.0 (3)	H16B—C16—H16C	109.5
C8—N3—N4	107.8 (3)	O3—C17—H17A	109.5
C9—N4—N3	107.6 (3)	O3—C17—H17B	109.5
N6—N5—H3	109 (3)	H17A—C17—H17B	109.5
N6—N5—H4	108 (3)	O3—C17—H17C	109.5
H3—N5—H4	113 (4)	H17A—C17—H17C	109.5
C25—N6—C24	106.0 (3)	H17B—C17—H17C	109.5
C25—N6—N5	123.5 (3)	O3—C18—C23	124.3 (4)
C24—N6—N5	129.8 (3)	O3—C18—C19	115.5 (3)
C24—N7—N8	108.2 (3)	C23—C18—C19	120.2 (3)
C25—N8—N7	107.8 (3)	C20—C19—C18	119.5 (3)
O1—C1—H1A	109.5	C20—C19—H19	120.3
O1—C1—H1B	109.5	C18—C19—H19	120.3
H1A—C1—H1B	109.5	C19—C20—C21	121.7 (4)
O1—C1—H1C	109.5	C19—C20—H20	119.2
H1A—C1—H1C	109.5	C21—C20—H20	119.2
H1B—C1—H1C	109.5	C22—C21—C20	117.5 (3)
O1—C2—C3	115.8 (3)	C22—C21—C24	124.0 (3)
O1—C2—C7	124.5 (4)	C20—C21—C24	118.5 (3)
C3—C2—C7	119.8 (3)	C21—C22—C23	121.9 (3)
C4—C3—C2	120.4 (3)	C21—C22—H22	119.0
C4—C3—H3A	119.8	C23—C22—H22	119.0
C2—C3—H3A	119.8	C18—C23—C22	119.1 (4)
C3—C4—C5	120.2 (4)	C18—C23—H23	120.5
C3—C4—H4A	119.9	C22—C23—H23	120.5
C5—C4—H4A	119.9	N7—C24—N6	108.3 (3)
C6—C5—C4	118.6 (3)	N7—C24—C21	123.7 (3)
C6—C5—C8	123.8 (3)	N6—C24—C21	128.0 (3)
C4—C5—C8	117.6 (4)	N8—C25—N6	109.7 (3)
C5—C6—C7	121.4 (3)	N8—C25—C26	124.4 (3)
C5—C6—H6	119.3	N6—C25—C26	126.0 (3)
C7—C6—H6	119.3	C31—C26—C27	118.8 (3)
C6—C7—C2	119.5 (4)	C31—C26—C25	118.7 (3)
C6—C7—H7	120.2	C27—C26—C25	122.4 (3)
C2—C7—H7	120.2	C28—C27—C26	119.8 (3)
N3—C8—N2	109.2 (3)	C28—C27—H27	120.1
N3—C8—C5	123.7 (3)	C26—C27—H27	120.1
N2—C8—C5	127.1 (3)	C27—C28—C29	120.5 (4)
N4—C9—N2	109.5 (3)	C27—C28—H28	119.7
N4—C9—C10	124.7 (3)	C29—C28—H28	119.7
N2—C9—C10	125.8 (3)	O4—C29—C30	124.4 (3)
C15—C10—C11	118.0 (3)	O4—C29—C28	115.3 (3)
C15—C10—C9	119.2 (3)	C30—C29—C28	120.3 (3)
C11—C10—C9	122.8 (3)	C29—C30—C31	118.9 (3)
C12—C11—C10	120.4 (3)	C29—C30—H30	120.6
C12—C11—H11	119.8	C31—C30—H30	120.6
C10—C11—H11	119.8	C30—C31—C26	121.7 (4)
C11—C12—C13	121.4 (4)	C30—C31—H31	119.2
C11—C12—H12	119.3	C26—C31—H31	119.2
C13—C12—H12	119.3	O4—C32—H32A	109.5
O2—C13—C12	116.8 (3)	O4—C32—H32B	109.5
O2—C13—C14	124.0 (3)	H32A—C32—H32B	109.5
C12—C13—C14	119.3 (3)	O4—C32—H32C	109.5
C15—C14—C13	119.2 (3)	H32A—C32—H32C	109.5
C15—C14—H14	120.4	H32B—C32—H32C	109.5
C8—N3—N4—C9	0.5 (4)	C9—C10—C15—C14	−177.7 (3)
C24—N7—N8—C25	0.2 (4)	C17—O3—C18—C23	−5.2 (6)
C1—O1—C2—C3	−175.3 (4)	C17—O3—C18—C19	174.2 (4)
C1—O1—C2—C7	4.1 (6)	O3—C18—C19—C20	−176.4 (4)
O1—C2—C3—C4	176.4 (4)	C23—C18—C19—C20	3.0 (6)
C7—C2—C3—C4	−3.0 (7)	C18—C19—C20—C21	−0.7 (6)
C2—C3—C4—C5	1.1 (7)	C19—C20—C21—C22	−2.1 (6)
C3—C4—C5—C6	1.8 (6)	C19—C20—C21—C24	177.2 (4)
C3—C4—C5—C8	179.7 (4)	C20—C21—C22—C23	2.8 (5)
C4—C5—C6—C7	−2.8 (6)	C24—C21—C22—C23	−176.4 (4)
C8—C5—C6—C7	179.4 (4)	O3—C18—C23—C22	177.1 (4)
C5—C6—C7—C2	1.0 (6)	C19—C18—C23—C22	−2.3 (6)
O1—C2—C7—C6	−177.4 (4)	C21—C22—C23—C18	−0.7 (6)
C3—C2—C7—C6	2.0 (6)	N8—N7—C24—N6	0.6 (4)
N4—N3—C8—N2	−0.6 (4)	N8—N7—C24—C21	−177.0 (3)
N4—N3—C8—C5	179.1 (3)	C25—N6—C24—N7	−1.2 (4)
C9—N2—C8—N3	0.5 (4)	N5—N6—C24—N7	−171.7 (4)
N1—N2—C8—N3	172.0 (3)	C25—N6—C24—C21	176.3 (4)
C9—N2—C8—C5	−179.3 (4)	N5—N6—C24—C21	5.8 (6)
N1—N2—C8—C5	−7.7 (6)	C22—C21—C24—N7	−166.4 (4)
C6—C5—C8—N3	159.5 (4)	C20—C21—C24—N7	14.3 (6)
C4—C5—C8—N3	−18.4 (5)	C22—C21—C24—N6	16.5 (6)
C6—C5—C8—N2	−20.8 (6)	C20—C21—C24—N6	−162.8 (4)
C4—C5—C8—N2	161.4 (4)	N7—N8—C25—N6	−1.0 (4)
N3—N4—C9—N2	−0.2 (4)	N7—N8—C25—C26	177.4 (3)
N3—N4—C9—C10	−177.9 (3)	C24—N6—C25—N8	1.4 (4)
C8—N2—C9—N4	−0.2 (4)	N5—N6—C25—N8	172.6 (3)
N1—N2—C9—N4	−171.3 (3)	C24—N6—C25—C26	−177.0 (3)
C8—N2—C9—C10	177.4 (3)	N5—N6—C25—C26	−5.8 (6)
N1—N2—C9—C10	6.3 (6)	N8—C25—C26—C31	−35.0 (5)
N4—C9—C10—C15	39.4 (5)	N6—C25—C26—C31	143.2 (4)
N2—C9—C10—C15	−137.9 (4)	N8—C25—C26—C27	142.9 (4)
N4—C9—C10—C11	−138.9 (4)	N6—C25—C26—C27	−38.9 (6)
N2—C9—C10—C11	43.8 (5)	C31—C26—C27—C28	0.0 (5)
C15—C10—C11—C12	−0.5 (5)	C25—C26—C27—C28	−177.9 (3)
C9—C10—C11—C12	177.8 (3)	C26—C27—C28—C29	0.9 (5)
C10—C11—C12—C13	0.8 (5)	C32—O4—C29—C30	7.6 (5)
C16—O2—C13—C12	170.4 (3)	C32—O4—C29—C28	−174.2 (3)
C16—O2—C13—C14	−8.6 (5)	C27—C28—C29—O4	−179.6 (3)
C11—C12—C13—O2	179.9 (3)	C27—C28—C29—C30	−1.3 (6)
C11—C12—C13—C14	−1.1 (5)	O4—C29—C30—C31	179.0 (3)
O2—C13—C14—C15	−179.9 (3)	C28—C29—C30—C31	0.9 (6)
C12—C13—C14—C15	1.2 (5)	C29—C30—C31—C26	0.0 (6)
C13—C14—C15—C10	−1.0 (5)	C27—C26—C31—C30	−0.4 (5)
C11—C10—C15—C14	0.6 (5)	C25—C26—C31—C30	177.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N8	0.86 (4)	2.20 (2)	3.027 (5)	162 (4)
N5—H3···N4i	0.86 (3)	2.18 (3)	3.029 (5)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N8	0.86 (4)	2.20 (2)	3.027 (5)	162 (4)
N5—H3⋯N4i	0.86 (3)	2.18 (3)	3.029 (5)	166 (3)

Symmetry code: (i) .