3,5-Bis(4-meth­oxy­phen­yl)-4H-1,2,4-triazol-4-amine

Yang, H.; Huang, Z.-D.; Yang, G.; Ng, S.W.

doi:10.1107/S1600536810030898

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2236

https://doi.org/10.1107/S1600536810030898

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3,5-Bis(4-methoxyphenyl)-4H-1,2,4-triazol-4-amine

Hui Yang,^a Zhan-Dong Huang,^a Guang Yang ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450001, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 1 August 2010; accepted 2 August 2010; online 11 August 2010)

The title compound, C₁₆H₁₆N₄O₂, crystallizes with two molecules in the asymmetric unit, which are related by a non-crystallographic centre of inversion. The phenylene rings are twisted out of the mean plane of the triazole ring by 19.3 (1) and 21.4 (1)° for one independent molecule and by 16.3 (1) and 18.1 (1)° for the other molecule. In the crystal, adjacent molecules 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_r = 296.33
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.147
S = 1.06
3459 reflections
417 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.29 e Å⁻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) x+1, y, z.

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030898/bt5318Isup2.hkl

checkCIF report

Comment top

The compound was intended for the synthesis of gold complexes as the two nitrogen atoms of the ring can possibly give rise to triangular-shaped trinuclear compounds. The parent compound, 3,5-diphenyl-1,2,4-triazol-4-amine, which exists in two polymorphic forms (Ikemi et al., 2002; Zhang et al., 2009), furnishes a number of metal derivatives. In the methoxy-substituted derivative (Scheme I), the five-membered triazole ring is planar but the phenylene rings are twisted out of the mean plane [19.3 (1), 21.4 (1) °; 16.3 (1), 18.1 (1) °] in the two indepedent molecules (Fig. 1). The twist angles are smaller than those noted in the parent compound. Adjacent molecules are linked by N–H_amino···N_triazole hydrogen bonds to form chain running along the a-axis (Fig. 2).

Related literature top

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 top

The compound was synthesized by using a literature method (Bentiss et al., 1999), and crystals were obtained upon recrystallzation from aqueous methanol.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the two independent molecules of C₁₆H₁₆N₄O₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded chain motif.

3,5-Bis(4-methoxyphenyl)-4H-1,2,4-triazol-4-amine top

Crystal data top

C₁₆H₁₆N₄O₂	F(000) = 624
M_r = 296.33	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0797P)² + 0.357P] where P = (F_o² + 2F_c²)/3
3459 reflections	(Δ/σ)_max = 0.001
417 parameters	Δρ_max = 0.48 e Å⁻³
5 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₆H₁₆N₄O₂	V = 1395.51 (19) Å³
M_r = 296.33	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 11.2232 (9) Å	µ = 0.10 mm⁻¹
b = 7.2386 (6) Å	T = 100 K
c = 17.9766 (14) Å	0.40 × 0.20 × 0.10 mm
β = 107.147 (1)°

Data collection top

Bruker SMART APEX diffractometer	2709 reflections with I > 2σ(I)
12717 measured reflections	R_int = 0.086
3459 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	5 restraints
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.48 e Å⁻³
3459 reflections	Δρ_min = −0.29 e Å⁻³
417 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₄O₂
M_r	296.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	11.2232 (9), 7.2386 (6), 17.9766 (14)
β (°)	107.147 (1)
V (Å³)	1395.51 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12717, 3459, 2709
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.147, 1.06
No. of reflections	3459
No. of parameters	417
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.29

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z.

Acknowledgements

We thank the National Science Foundation of China (No. J0830412) and the University of Malaya for supporting this study.

References

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