6-Isopropyl-3-phenyl-5-(p-tol-yloxy)-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one: whole-mol-ecule disorder.

The title compound, C(20)H(19)N(5)O(2), exhibits whole-mol-ecule disorder the refined ratios of the two components being 0.57 (2):0.43 (2). In the major component, the essentially planar [maximum deviation 0.033 (17) Å] fused pyrimidine and triazole ring system forms a dihedral angle of 10.5 (3)° with the phenyl ring, while in the minor component of disorder this angle is 27.5 (5)°. The crystal structure is stabilized by π-π stacking inter-actions between symmetry-related triazole and pyrimidine rings, with centroid-centroid distances of 3.594 (10) Å.

Related literature

For the biological activity of 8-aza­guanine derivatives see: Roblin et al. (1945 ▶); Ding et al. (2004 ▶); Mitchell et al. (1950 ▶); Levine et al. (1963 ▶); Montgomery et al. (1962 ▶)); Yamamoto et al. (1967 ▶); Bariana (1971 ▶); Holland et al. (1975 ▶). For related structures, see: Ferguson et al. (1998 ▶); Zhao, Xie et al. (2005 ▶); Zhao, Hu et al. (2005 ▶); Zhao, Wang & Ding (2005 ▶); Chen & Shi (2006 ▶); Maldonado et al. (2006 ▶); Xiao et al. (2007 ▶); Wang et al. (2006 ▶, 2008 ▶); Zeng, Deng et al. (2009 ▶), Zeng, Liu et al. (2009 ▶). For examples of whole-mol­ecule disorder, see: Kirsop et al. (2006 ▶); Cox & Wardell (2003 ▶). For the preparation, see: Zeng et al. (2006 ▶).

Experimental

Crystal data

C20H19N5O2

M = 361.40

Orthorhombic,

a = 10.2335 (6) Å

b = 21.8532 (12) Å

c = 16.7441 (9) Å

V = 3744.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

21260 measured reflections

2285 independent reflections

1790 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.144

S = 1.06

2285 reflections

446 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039798/lh2904sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039798/lh2904Isup2.hkl

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

C20H19N5O2	F(000) = 1520
Mr = 361.40	Dx = 1.282 Mg m−3
Orthorhombic, C2221	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 7338 reflections
a = 10.2335 (6) Å	θ = 2.2–22.6°
b = 21.8532 (12) Å	µ = 0.09 mm−1
c = 16.7441 (9) Å	T = 298 K
V = 3744.6 (4) Å3	Block, colorless
Z = 8	0.20 × 0.20 × 0.20 mm

Bruker SMART CCD diffractometer	1790 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 27.0°, θmin = 2.2°
φ and ω scans	h = −13→13
21260 measured reflections	k = −27→27
2285 independent reflections	l = −21→21

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1088P)2 + 0.0578P] where P = (Fo2 + 2Fc2)/3
2285 reflections	(Δ/σ)max < 0.001
446 parameters	Δρmax = 0.17 e Å−3
15 restraints	Δρmin = −0.17 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	Occ. (<1)
O1	0.5967 (13)	0.0694 (5)	0.1729 (8)	0.111 (2)	0.57 (2)
O2	0.3920 (17)	0.2076 (8)	0.0153 (9)	0.096 (3)	0.57 (2)
N1	0.6946 (14)	0.2696 (5)	0.2174 (10)	0.069 (2)	0.57 (2)
N2	0.7566 (13)	0.2328 (6)	0.2727 (7)	0.082 (2)	0.57 (2)
N3	0.7249 (10)	0.1753 (5)	0.2602 (6)	0.082 (3)	0.57 (2)
N4	0.5505 (14)	0.2489 (7)	0.1072 (8)	0.103 (5)	0.57 (2)
N5	0.500 (2)	0.1435 (10)	0.0927 (11)	0.085 (3)	0.57 (2)
C1	0.7134 (7)	0.3323 (3)	0.2161 (3)	0.0691 (17)	0.57 (2)
C2	0.6409 (8)	0.3694 (3)	0.1653 (6)	0.105 (3)	0.57 (2)
H2	0.5805	0.3521	0.1305	0.126*	0.57 (2)
C3	0.6587 (8)	0.4325 (3)	0.1665 (7)	0.117 (3)	0.57 (2)
H3	0.6102	0.4573	0.1325	0.141*	0.57 (2)
C4	0.7490 (7)	0.4584 (4)	0.2184 (5)	0.113 (3)	0.57 (2)
H4	0.7609	0.5006	0.2192	0.135*	0.57 (2)
C5	0.8215 (8)	0.4213 (5)	0.2692 (3)	0.110 (3)	0.57 (2)
H5	0.8819	0.4386	0.3040	0.132*	0.57 (2)
C6	0.8037 (8)	0.3582 (5)	0.2681 (3)	0.102 (3)	0.57 (2)
H6	0.8522	0.3334	0.3021	0.123*	0.57 (2)
C7	0.6443 (19)	0.1776 (9)	0.1971 (12)	0.081 (3)	0.57 (2)
C8	0.6235 (13)	0.2323 (6)	0.1690 (7)	0.062 (2)	0.57 (2)
C9	0.489 (3)	0.2026 (13)	0.0766 (15)	0.090 (5)	0.57 (2)
C10	0.586 (2)	0.1249 (10)	0.1598 (12)	0.085 (4)	0.57 (2)
C11	0.3987 (9)	0.2670 (3)	−0.0196 (6)	0.104 (4)	0.57 (2)
C12	0.3310 (9)	0.3155 (4)	0.0145 (5)	0.082 (3)	0.57 (2)
H12	0.2821	0.3095	0.0606	0.099*	0.57 (2)
C13	0.3364 (9)	0.3732 (3)	−0.0204 (6)	0.090 (2)	0.57 (2)
H13	0.2911	0.4057	0.0023	0.108*	0.57 (2)
C14	0.4095 (8)	0.3823 (4)	−0.0894 (6)	0.084 (2)	0.57 (2)
C15	0.4772 (9)	0.3337 (6)	−0.1235 (5)	0.097 (3)	0.57 (2)
H15	0.5261	0.3398	−0.1696	0.116*	0.57 (2)
C16	0.4718 (10)	0.2760 (5)	−0.0886 (6)	0.095 (2)	0.57 (2)
H16	0.5171	0.2435	−0.1113	0.114*	0.57 (2)
C17	0.4124 (14)	0.4466 (7)	−0.1241 (10)	0.136 (4)	0.57 (2)
H17A	0.3397	0.4696	−0.1038	0.204*	0.57 (2)
H17B	0.4069	0.4445	−0.1812	0.204*	0.57 (2)
H17C	0.4925	0.4664	−0.1090	0.204*	0.57 (2)
C18	0.4324 (15)	0.0923 (7)	0.0447 (9)	0.095 (3)	0.57 (2)
H18	0.4657	0.0539	0.0670	0.114*	0.57 (2)
C19	0.2897 (15)	0.0907 (8)	0.0583 (10)	0.125 (5)	0.57 (2)
H19A	0.2496	0.1250	0.0320	0.188*	0.57 (2)
H19B	0.2723	0.0928	0.1145	0.188*	0.57 (2)
H19C	0.2545	0.0534	0.0371	0.188*	0.57 (2)
C20	0.4717 (15)	0.0914 (10)	−0.0428 (10)	0.112 (3)	0.57 (2)
H20A	0.4440	0.0536	−0.0666	0.167*	0.57 (2)
H20B	0.5650	0.0950	−0.0470	0.167*	0.57 (2)
H20C	0.4311	0.1251	−0.0700	0.167*	0.57 (2)
C1A	0.7079 (12)	0.3091 (7)	0.2237 (6)	0.094 (3)	0.43 (2)
C2A	0.6177 (10)	0.3523 (7)	0.1975 (9)	0.111 (4)	0.43 (2)
H2A	0.5398	0.3396	0.1742	0.134*	0.43 (2)
C3A	0.6440 (10)	0.4143 (7)	0.2062 (12)	0.142 (5)	0.43 (2)
H3A	0.5837	0.4432	0.1887	0.170*	0.43 (2)
C4A	0.7605 (13)	0.4332 (8)	0.2410 (9)	0.134 (5)	0.43 (2)
H4A	0.7781	0.4748	0.2468	0.161*	0.43 (2)
C5A	0.8507 (13)	0.3901 (10)	0.2672 (6)	0.140 (6)	0.43 (2)
H5A	0.9286	0.4028	0.2905	0.168*	0.43 (2)
C6A	0.8244 (12)	0.3281 (10)	0.2585 (7)	0.136 (5)	0.43 (2)
H6A	0.8848	0.2992	0.2761	0.163*	0.43 (2)
C7A	0.6291 (16)	0.1569 (9)	0.1872 (9)	0.060 (3)	0.43 (2)
C8A	0.610 (2)	0.2128 (9)	0.1634 (11)	0.070 (4)	0.43 (2)
C9A	0.480 (3)	0.1980 (13)	0.0641 (17)	0.067 (4)	0.43 (2)
C10A	0.559 (3)	0.1085 (15)	0.1430 (15)	0.081 (4)	0.43 (2)
C11A	0.4049 (8)	0.2736 (4)	−0.0202 (5)	0.056 (2)	0.43 (2)
C12A	0.3332 (13)	0.3137 (5)	0.0270 (7)	0.102 (5)	0.43 (2)
H12A	0.2928	0.2996	0.0732	0.122*	0.43 (2)
C13A	0.3218 (16)	0.3748 (5)	0.0050 (10)	0.122 (5)	0.43 (2)
H13A	0.2738	0.4016	0.0366	0.147*	0.43 (2)
C14A	0.3822 (16)	0.3958 (4)	−0.0641 (10)	0.094 (4)	0.43 (2)
C15A	0.4539 (15)	0.3557 (7)	−0.1113 (6)	0.089 (4)	0.43 (2)
H15A	0.4943	0.3698	−0.1576	0.107*	0.43 (2)
C16A	0.4653 (11)	0.2946 (6)	−0.0894 (5)	0.093 (3)	0.43 (2)
H16A	0.5133	0.2678	−0.1210	0.111*	0.43 (2)
C17A	0.377 (2)	0.4628 (10)	−0.0866 (14)	0.147 (6)	0.43 (2)
H17D	0.3001	0.4811	−0.0642	0.221*	0.43 (2)
H17E	0.3749	0.4667	−0.1437	0.221*	0.43 (2)
H17F	0.4532	0.4832	−0.0662	0.221*	0.43 (2)
C18A	0.3959 (18)	0.0886 (12)	0.0309 (13)	0.106 (5)	0.43 (2)
H18A	0.4062	0.0485	0.0563	0.127*	0.43 (2)
C19A	0.2578 (17)	0.1054 (11)	0.0417 (11)	0.107 (4)	0.43 (2)
H19D	0.2372	0.1396	0.0081	0.160*	0.43 (2)
H19E	0.2427	0.1162	0.0965	0.160*	0.43 (2)
H19F	0.2034	0.0713	0.0276	0.160*	0.43 (2)
C20A	0.441 (3)	0.0808 (14)	−0.0529 (15)	0.134 (8)	0.43 (2)
H20D	0.3923	0.0485	−0.0778	0.200*	0.43 (2)
H20E	0.5323	0.0708	−0.0532	0.200*	0.43 (2)
H20F	0.4274	0.1183	−0.0818	0.200*	0.43 (2)
O1A	0.5643 (15)	0.0529 (8)	0.1518 (9)	0.105 (3)	0.43 (2)
O2A	0.4187 (19)	0.2151 (8)	0.0014 (9)	0.076 (3)	0.43 (2)
N1A	0.686 (2)	0.2462 (10)	0.2155 (15)	0.080 (4)	0.43 (2)
N2A	0.7450 (14)	0.2046 (8)	0.2667 (8)	0.086 (5)	0.43 (2)
N3A	0.7055 (19)	0.1495 (10)	0.2479 (11)	0.094 (4)	0.43 (2)
N4A	0.5407 (11)	0.2413 (7)	0.1048 (5)	0.057 (2)	0.43 (2)
N5A	0.479 (2)	0.1328 (10)	0.0799 (11)	0.074 (4)	0.43 (2)

	U11	U22	U33	U12	U13	U23
O1	0.131 (6)	0.082 (4)	0.120 (6)	−0.009 (3)	−0.002 (4)	0.020 (4)
O2	0.090 (5)	0.086 (5)	0.111 (7)	−0.007 (3)	−0.014 (4)	0.009 (4)
N1	0.066 (3)	0.087 (7)	0.055 (2)	−0.002 (6)	−0.0045 (19)	0.004 (7)
N2	0.091 (3)	0.094 (6)	0.061 (2)	0.008 (5)	−0.014 (2)	0.006 (4)
N3	0.097 (7)	0.085 (10)	0.064 (5)	−0.003 (8)	−0.011 (4)	0.016 (8)
N4	0.111 (8)	0.096 (6)	0.103 (7)	0.004 (5)	−0.015 (5)	−0.008 (4)
N5	0.088 (5)	0.077 (5)	0.091 (6)	−0.010 (3)	0.001 (4)	−0.014 (4)
C1	0.063 (2)	0.092 (4)	0.052 (2)	0.000 (3)	0.000 (2)	−0.007 (2)
C2	0.103 (5)	0.108 (5)	0.104 (5)	0.001 (3)	−0.034 (4)	−0.005 (4)
C3	0.128 (5)	0.094 (4)	0.129 (7)	0.010 (4)	−0.028 (5)	−0.012 (4)
C4	0.140 (6)	0.096 (4)	0.102 (5)	0.003 (4)	−0.006 (4)	−0.028 (4)
C5	0.131 (6)	0.114 (6)	0.086 (4)	−0.008 (5)	−0.028 (4)	−0.027 (4)
C6	0.122 (6)	0.115 (7)	0.070 (3)	−0.014 (5)	−0.031 (3)	−0.003 (3)
C7	0.086 (5)	0.079 (10)	0.079 (5)	−0.004 (5)	0.003 (4)	0.002 (5)
C8	0.060 (3)	0.070 (5)	0.056 (4)	−0.002 (4)	0.002 (3)	0.000 (4)
C9	0.084 (6)	0.109 (11)	0.077 (9)	0.020 (7)	−0.009 (6)	0.007 (6)
C10	0.084 (9)	0.082 (12)	0.089 (12)	0.003 (6)	0.013 (7)	0.018 (7)
C11	0.093 (7)	0.119 (9)	0.101 (9)	−0.009 (6)	−0.017 (6)	−0.010 (7)
C12	0.075 (5)	0.095 (7)	0.077 (3)	0.002 (4)	−0.002 (3)	−0.001 (3)
C13	0.077 (4)	0.090 (5)	0.104 (6)	0.019 (3)	−0.004 (4)	0.001 (3)
C14	0.071 (4)	0.097 (5)	0.083 (5)	0.009 (4)	−0.003 (3)	0.004 (4)
C15	0.092 (4)	0.112 (7)	0.086 (4)	0.025 (5)	−0.002 (3)	0.009 (5)
C16	0.090 (4)	0.112 (5)	0.083 (4)	0.025 (4)	0.000 (3)	−0.004 (3)
C17	0.129 (7)	0.128 (8)	0.152 (10)	0.006 (5)	−0.005 (7)	0.040 (7)
C18	0.102 (6)	0.075 (4)	0.106 (6)	−0.008 (4)	0.005 (5)	−0.016 (4)
C19	0.121 (9)	0.114 (7)	0.140 (9)	−0.031 (7)	0.000 (7)	−0.016 (6)
C20	0.111 (6)	0.113 (6)	0.111 (6)	−0.006 (5)	0.015 (5)	−0.052 (4)
C1A	0.098 (6)	0.115 (10)	0.071 (5)	−0.016 (9)	0.006 (4)	0.007 (8)
C2A	0.110 (6)	0.112 (7)	0.113 (8)	0.008 (6)	0.001 (6)	−0.018 (6)
C3A	0.148 (10)	0.133 (9)	0.145 (12)	0.011 (8)	−0.008 (9)	−0.010 (9)
C4A	0.166 (14)	0.131 (10)	0.104 (9)	−0.021 (9)	0.015 (9)	−0.039 (10)
C5A	0.165 (14)	0.154 (16)	0.102 (7)	−0.014 (11)	−0.009 (7)	−0.015 (9)
C6A	0.156 (11)	0.162 (13)	0.090 (6)	−0.024 (9)	−0.019 (6)	−0.010 (8)
C7A	0.065 (6)	0.068 (12)	0.049 (5)	0.000 (6)	0.000 (4)	0.008 (6)
C8A	0.071 (5)	0.081 (10)	0.058 (4)	0.003 (7)	0.003 (4)	0.002 (7)
C9A	0.070 (8)	0.075 (7)	0.056 (6)	0.013 (5)	−0.001 (4)	−0.006 (4)
C10A	0.083 (10)	0.094 (16)	0.067 (7)	0.010 (8)	0.011 (6)	0.014 (7)
C11A	0.055 (4)	0.064 (4)	0.049 (4)	0.012 (3)	−0.021 (3)	−0.001 (3)
C12A	0.097 (10)	0.107 (11)	0.101 (7)	0.022 (8)	−0.004 (6)	0.015 (6)
C13A	0.109 (8)	0.137 (11)	0.121 (10)	0.013 (7)	−0.006 (7)	0.005 (7)
C14A	0.085 (8)	0.101 (7)	0.096 (10)	0.011 (5)	−0.016 (6)	0.000 (6)
C15A	0.090 (8)	0.103 (9)	0.074 (5)	0.005 (7)	−0.003 (4)	0.000 (6)
C16A	0.094 (6)	0.112 (8)	0.072 (6)	0.014 (5)	−0.018 (5)	−0.014 (5)
C17A	0.154 (14)	0.129 (11)	0.159 (15)	−0.003 (9)	−0.017 (11)	0.024 (10)
C18A	0.104 (11)	0.111 (10)	0.103 (8)	0.005 (8)	0.003 (7)	0.014 (7)
C19A	0.093 (7)	0.131 (11)	0.096 (7)	0.005 (6)	0.011 (6)	−0.011 (6)
C20A	0.150 (16)	0.133 (15)	0.118 (10)	0.004 (11)	−0.006 (10)	−0.020 (9)
O1A	0.121 (7)	0.090 (7)	0.106 (6)	0.010 (5)	−0.006 (5)	0.028 (5)
O2A	0.092 (8)	0.068 (4)	0.069 (4)	−0.005 (4)	−0.025 (5)	0.002 (4)
N1A	0.080 (6)	0.105 (12)	0.056 (4)	0.008 (8)	0.000 (4)	0.004 (9)
N2A	0.097 (8)	0.091 (15)	0.069 (6)	−0.003 (13)	−0.004 (5)	0.015 (13)
N3A	0.094 (6)	0.116 (11)	0.072 (5)	0.006 (8)	−0.005 (4)	0.016 (7)
N4A	0.048 (3)	0.076 (5)	0.046 (4)	0.006 (3)	−0.012 (3)	0.001 (3)
N5A	0.087 (8)	0.071 (9)	0.063 (5)	0.011 (6)	0.001 (5)	0.005 (5)

O1—C10	1.24 (3)	C1A—C2A	1.3900
O2—C11	1.425 (17)	C1A—C6A	1.3900
O2—C9	1.43 (2)	C1A—N1A	1.401 (15)
N1—C8	1.360 (15)	C2A—C3A	1.3900
N1—N2	1.381 (19)	C2A—H2A	0.9300
N1—C1	1.383 (9)	C3A—C4A	1.3900
N2—N3	1.315 (9)	C3A—H3A	0.9300
N3—C7	1.34 (3)	C4A—C5A	1.3900
N4—C9	1.300 (13)	C4A—H4A	0.9300
N4—C8	1.328 (11)	C5A—C6A	1.3900
N5—C9	1.32 (3)	C5A—H5A	0.9300
N5—C10	1.48 (3)	C6A—H6A	0.9300
N5—C18	1.543 (11)	C7A—N3A	1.29 (3)
C1—C2	1.3900	C7A—C8A	1.30 (2)
C1—C6	1.3900	C7A—C10A	1.477 (16)
C2—C3	1.3900	C8A—N4A	1.358 (13)
C2—H2	0.9300	C8A—N1A	1.38 (2)
C3—C4	1.3900	C9A—O2A	1.28 (3)
C3—H3	0.9300	C9A—N4A	1.321 (12)
C4—C5	1.3900	C9A—N5A	1.45 (3)
C4—H4	0.9300	C10A—O1A	1.23 (4)
C5—C6	1.3900	C10A—N5A	1.44 (4)
C5—H5	0.9300	C11A—O2A	1.34 (2)
C6—H6	0.9300	C11A—C12A	1.3900
C7—C8	1.30 (2)	C11A—C16A	1.3900
C7—C10	1.440 (13)	C12A—C13A	1.3900
C11—C12	1.3900	C12A—H12A	0.9300
C11—C16	1.3900	C13A—C14A	1.3900
C12—C13	1.3900	C13A—H13A	0.9300
C12—H12	0.9300	C14A—C15A	1.3900
C13—C14	1.3900	C14A—C17A	1.51 (2)
C13—H13	0.9300	C15A—C16A	1.3900
C14—C15	1.3900	C15A—H15A	0.9300
C14—C17	1.522 (14)	C16A—H16A	0.9300
C15—C16	1.3900	C17A—H17D	0.9600
C15—H15	0.9300	C17A—H17E	0.9600
C16—H16	0.9300	C17A—H17F	0.9600
C17—H17A	0.9600	C18A—C19A	1.471 (14)
C17—H17B	0.9600	C18A—C20A	1.487 (14)
C17—H17C	0.9600	C18A—N5A	1.528 (15)
C18—C19	1.478 (12)	C18A—H18A	0.9800
C18—C20	1.519 (12)	C19A—H19D	0.9600
C18—H18	0.9800	C19A—H19E	0.9600
C19—H19A	0.9600	C19A—H19F	0.9600
C19—H19B	0.9600	C20A—H20D	0.9600
C19—H19C	0.9600	C20A—H20E	0.9600
C20—H20A	0.9600	C20A—H20F	0.9600
C20—H20B	0.9600	N1A—N2A	1.39 (3)
C20—H20C	0.9600	N2A—N3A	1.309 (14)
C11—O2—C9	109.3 (16)	C3A—C4A—C5A	120.0
C8—N1—N2	107.2 (9)	C3A—C4A—H4A	120.0
C8—N1—C1	131.2 (12)	C5A—C4A—H4A	120.0
N2—N1—C1	121.6 (11)	C6A—C5A—C4A	120.0
N3—N2—N1	109.6 (11)	C6A—C5A—H5A	120.0
N2—N3—C7	104.1 (12)	C4A—C5A—H5A	120.0
C9—N4—C8	111.6 (12)	C5A—C6A—C1A	120.0
C9—N5—C10	118.4 (13)	C5A—C6A—H6A	120.0
C9—N5—C18	124.0 (17)	C1A—C6A—H6A	120.0
C10—N5—C18	117.6 (17)	N3A—C7A—C8A	116.8 (15)
N1—C1—C2	120.9 (7)	N3A—C7A—C10A	126.7 (17)
N1—C1—C6	119.1 (7)	C8A—C7A—C10A	116.4 (18)
C2—C1—C6	120.0	C7A—C8A—N4A	136.9 (15)
C3—C2—C1	120.0	C7A—C8A—N1A	102.5 (14)
C3—C2—H2	120.0	N4A—C8A—N1A	120.6 (16)
C1—C2—H2	120.0	O2A—C9A—N4A	116 (2)
C4—C3—C2	120.0	O2A—C9A—N5A	115.8 (16)
C4—C3—H3	120.0	N4A—C9A—N5A	127.8 (19)
C2—C3—H3	120.0	O1A—C10A—N5A	118.8 (15)
C5—C4—C3	120.0	O1A—C10A—C7A	129 (2)
C5—C4—H4	120.0	N5A—C10A—C7A	112 (2)
C3—C4—H4	120.0	O2A—C11A—C12A	120.3 (9)
C4—C5—C6	120.0	O2A—C11A—C16A	119.7 (9)
C4—C5—H5	120.0	C12A—C11A—C16A	120.0
C6—C5—H5	120.0	C11A—C12A—C13A	120.0
C5—C6—C1	120.0	C11A—C12A—H12A	120.0
C5—C6—H6	120.0	C13A—C12A—H12A	120.0
C1—C6—H6	120.0	C14A—C13A—C12A	120.0
C8—C7—N3	114.7 (9)	C14A—C13A—H13A	120.0
C8—C7—C10	120.5 (16)	C12A—C13A—H13A	120.0
N3—C7—C10	124.7 (17)	C15A—C14A—C13A	120.0
C7—C8—N4	128.6 (12)	C15A—C14A—C17A	119.1 (10)
C7—C8—N1	104.4 (11)	C13A—C14A—C17A	120.8 (10)
N4—C8—N1	127.0 (13)	C14A—C15A—C16A	120.0
N4—C9—N5	129.5 (18)	C14A—C15A—H15A	120.0
N4—C9—O2	124 (2)	C16A—C15A—H15A	120.0
N5—C9—O2	106.5 (16)	C15A—C16A—C11A	120.0
O1—C10—C7	131.8 (17)	C15A—C16A—H16A	120.0
O1—C10—N5	117.2 (13)	C11A—C16A—H16A	120.0
C7—C10—N5	110.9 (16)	C14A—C17A—H17D	109.5
C12—C11—C16	120.0	C14A—C17A—H17E	109.5
C12—C11—O2	120.2 (8)	H17D—C17A—H17E	109.5
C16—C11—O2	119.8 (8)	C14A—C17A—H17F	109.5
C13—C12—C11	120.0	H17D—C17A—H17F	109.5
C13—C12—H12	120.0	H17E—C17A—H17F	109.5
C11—C12—H12	120.0	C19A—C18A—C20A	116.2 (14)
C12—C13—C14	120.0	C19A—C18A—N5A	108.2 (19)
C12—C13—H13	120.0	C20A—C18A—N5A	113.9 (17)
C14—C13—H13	120.0	C19A—C18A—H18A	105.9
C15—C14—C13	120.0	C20A—C18A—H18A	105.9
C15—C14—C17	122.7 (7)	N5A—C18A—H18A	105.9
C13—C14—C17	117.3 (7)	C18A—C19A—H19D	109.5
C14—C15—C16	120.0	C18A—C19A—H19E	109.5
C14—C15—H15	120.0	H19D—C19A—H19E	109.5
C16—C15—H15	120.0	C18A—C19A—H19F	109.5
C15—C16—C11	120.0	H19D—C19A—H19F	109.5
C15—C16—H16	120.0	H19E—C19A—H19F	109.5
C11—C16—H16	120.0	C18A—C20A—H20D	109.5
C19—C18—C20	114.2 (11)	C18A—C20A—H20E	109.5
C19—C18—N5	112.4 (12)	H20D—C20A—H20E	109.5
C20—C18—N5	113.1 (13)	C18A—C20A—H20F	109.5
C19—C18—H18	105.4	H20D—C20A—H20F	109.5
C20—C18—H18	105.4	H20E—C20A—H20F	109.5
N5—C18—H18	105.4	C9A—O2A—C11A	123.7 (16)
C2A—C1A—C6A	120.0	C8A—N1A—N2A	107.0 (11)
C2A—C1A—N1A	121.8 (13)	C8A—N1A—C1A	132 (2)
C6A—C1A—N1A	118.2 (13)	N2A—N1A—C1A	121 (2)
C3A—C2A—C1A	120.0	N3A—N2A—N1A	108.5 (17)
C3A—C2A—H2A	120.0	C7A—N3A—N2A	105.1 (19)
C1A—C2A—H2A	120.0	C9A—N4A—C8A	106.8 (13)
C2A—C3A—C4A	120.0	C10A—N5A—C9A	119.7 (16)
C2A—C3A—H3A	120.0	C10A—N5A—C18A	118.5 (17)
C4A—C3A—H3A	120.0	C9A—N5A—C18A	121.8 (18)