4-(3-Methoxy-phen-yl)-3-[2-(4-methoxy-phen-yl)eth-yl]-1H-1,2,4-triazol-5(4H)-one.

The asymmetric unit of the title compound, C(18)H(19)N(3)O(3), contains two crystallographically independent but similar mol-ecules. The triazole ring is oriented with respect to the benzene rings to form dihedral angles of 57.96 (6) and 7.01 (6)° in one mol-ecule, and 64.37 (5) and 10.73 (5)° in the other. The two independent mol-ecules are linked into a dimer by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the biological activities of triazole derivatives, see: Demirbas et al. (2002 ▶); Holla et al. (1998 ▶); Omar et al. (1986 ▶); Paulvannan et al. (2000 ▶); Turan-Zitouni et al. (1999 ▶); Kritsanida et al. (2002 ▶). For related structures, see: Öztürk et al. (2004a ▶,b ▶). For hydrogen-bond graph-set terminology, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C18H19N3O3

M = 325.36

Monoclinic,

a = 26.784 (4) Å

b = 14.824 (2) Å

c = 8.1108 (11) Å

β = 96.522 (3)°

V = 3199.5 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 (2) K

0.50 × 0.50 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

18196 measured reflections

6524 independent reflections

4463 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.083

S = 0.93

6524 reflections

445 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536809002840/rz2291sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002840/rz2291Isup2.hkl

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

C18H19N3O3	F(000) = 1376
Mr = 325.36	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Melting point: 407(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 26.784 (4) Å	Cell parameters from 1009 reflections
b = 14.824 (2) Å	θ = 2.7–26.4°
c = 8.1108 (11) Å	µ = 0.09 mm−1
β = 96.522 (3)°	T = 100 K
V = 3199.5 (8) Å3	Irregular, colourless
Z = 8	0.50 × 0.50 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	4463 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
graphite	θmax = 26.4°, θmin = 2.1°
φ and ω scans	h = −29→33
18196 measured reflections	k = −9→18
6524 independent reflections	l = −10→9

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.022P)2] where P = (Fo2 + 2Fc2)/3
6524 reflections	(Δ/σ)max = 0.001
445 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 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
O1	0.80652 (4)	1.26410 (8)	0.38630 (14)	0.0241 (3)
O2	1.01067 (4)	1.08446 (8)	0.35402 (14)	0.0250 (3)
O3	0.88400 (4)	0.52515 (8)	0.49269 (14)	0.0224 (3)
N1	0.83241 (5)	1.11201 (9)	0.40707 (16)	0.0168 (3)
N2	0.76150 (5)	1.04721 (9)	0.30095 (16)	0.0200 (3)
N3	0.75591 (5)	1.14005 (10)	0.30968 (18)	0.0210 (3)
H3N	0.7259 (6)	1.1699 (13)	0.258 (2)	0.049 (6)*
C1	0.80770 (6)	1.03201 (11)	0.36030 (19)	0.0165 (4)
C2	0.79850 (6)	1.18218 (12)	0.3694 (2)	0.0196 (4)
C3	0.88409 (6)	1.12582 (11)	0.4688 (2)	0.0170 (4)
C4	0.92115 (6)	1.09601 (11)	0.37531 (19)	0.0176 (4)
H4	0.9124	1.0662	0.2724	0.021*
C5	0.97099 (6)	1.11055 (11)	0.4347 (2)	0.0188 (4)
C6	0.98332 (6)	1.15633 (12)	0.5836 (2)	0.0229 (4)
H6	1.0176	1.1670	0.6233	0.027*
C7	0.94588 (6)	1.18619 (12)	0.6732 (2)	0.0232 (4)
H7	0.9546	1.2175	0.7746	0.028*
C8	0.89570 (6)	1.17121 (11)	0.6175 (2)	0.0208 (4)
H8	0.8699	1.1916	0.6798	0.025*
C9	1.00001 (6)	1.04758 (13)	0.1916 (2)	0.0273 (5)
H9A	0.9791	0.9936	0.1962	0.041*
H9B	1.0316	1.0314	0.1485	0.041*
H9C	0.9821	1.0924	0.1184	0.041*
C10	0.82961 (6)	0.93970 (11)	0.37288 (19)	0.0184 (4)
H10A	0.8628	0.9416	0.3299	0.022*
H10B	0.8077	0.8993	0.2991	0.022*
C11	0.83669 (6)	0.89770 (11)	0.54600 (19)	0.0199 (4)
H11A	0.8646	0.9285	0.6145	0.024*
H11B	0.8057	0.9059	0.6002	0.024*
C12	0.84841 (6)	0.79782 (12)	0.53503 (19)	0.0166 (4)
C13	0.89660 (6)	0.76489 (12)	0.57477 (19)	0.0199 (4)
H13	0.9228	0.8051	0.6154	0.024*
C14	0.90727 (6)	0.67427 (12)	0.5562 (2)	0.0204 (4)
H14	0.9407	0.6532	0.5820	0.024*
C15	0.86938 (6)	0.61408 (11)	0.50016 (19)	0.0169 (4)
C16	0.82093 (6)	0.64531 (12)	0.46004 (19)	0.0178 (4)
H16	0.7947	0.6049	0.4210	0.021*
C17	0.81113 (6)	0.73673 (12)	0.47759 (19)	0.0189 (4)
H17	0.7778	0.7581	0.4493	0.023*
C18	0.84577 (6)	0.45979 (12)	0.4460 (2)	0.0233 (4)
H18A	0.8198	0.4635	0.5218	0.035*
H18B	0.8606	0.3993	0.4518	0.035*
H18C	0.8307	0.4718	0.3323	0.035*
O4	0.32218 (4)	−0.25770 (8)	0.33832 (14)	0.0232 (3)
O5	0.52563 (4)	−0.08829 (9)	0.35036 (14)	0.0252 (3)
O6	0.38708 (4)	0.49050 (8)	0.53429 (13)	0.0214 (3)
N4	0.34705 (5)	−0.10875 (9)	0.40056 (16)	0.0167 (3)
N5	0.27715 (5)	−0.03721 (9)	0.30255 (17)	0.0200 (3)
N6	0.27211 (5)	−0.13024 (9)	0.28110 (18)	0.0198 (3)
H6N	0.2432 (6)	−0.1546 (12)	0.223 (2)	0.034 (5)*
C19	0.32257 (6)	−0.02667 (11)	0.3744 (2)	0.0173 (4)
C20	0.31384 (6)	−0.17568 (12)	0.3389 (2)	0.0182 (4)
C21	0.39848 (6)	−0.12574 (11)	0.4633 (2)	0.0161 (4)
C22	0.43614 (6)	−0.09321 (11)	0.37456 (19)	0.0168 (4)
H22	0.4281	−0.0577	0.2777	0.020*
C23	0.48550 (6)	−0.11357 (11)	0.4300 (2)	0.0177 (4)
C24	0.49701 (6)	−0.16566 (12)	0.5723 (2)	0.0219 (4)
H24	0.5310	−0.1801	0.6096	0.026*
C25	0.45893 (6)	−0.19599 (12)	0.6587 (2)	0.0234 (4)
H25	0.4670	−0.2306	0.7567	0.028*
C26	0.40919 (6)	−0.17697 (12)	0.6052 (2)	0.0210 (4)
H26	0.3830	−0.1986	0.6646	0.025*
C27	0.51482 (6)	−0.04444 (13)	0.1937 (2)	0.0276 (4)
H27A	0.4942	−0.0842	0.1171	0.041*
H27B	0.5463	−0.0306	0.1483	0.041*
H27C	0.4965	0.0117	0.2082	0.041*
C28	0.34597 (6)	0.06097 (11)	0.4281 (2)	0.0192 (4)
H28A	0.3745	0.0731	0.3635	0.023*
H28B	0.3594	0.0571	0.5467	0.023*
C29	0.30904 (6)	0.13794 (11)	0.4045 (2)	0.0253 (4)
H29A	0.2825	0.1279	0.4782	0.030*
H29B	0.2927	0.1363	0.2887	0.030*
C30	0.33070 (6)	0.23100 (11)	0.4386 (2)	0.0179 (4)
C31	0.37623 (6)	0.24682 (12)	0.5333 (2)	0.0201 (4)
H31	0.3953	0.1972	0.5803	0.024*
C32	0.39445 (6)	0.33361 (11)	0.5607 (2)	0.0195 (4)
H32	0.4262	0.3431	0.6233	0.023*
C33	0.36632 (6)	0.40670 (11)	0.49654 (19)	0.0166 (4)
C34	0.32082 (6)	0.39336 (12)	0.40142 (19)	0.0182 (4)
H34	0.3015	0.4430	0.3559	0.022*
C35	0.30397 (6)	0.30552 (12)	0.3740 (2)	0.0199 (4)
H35	0.2728	0.2960	0.3080	0.024*
C36	0.35951 (6)	0.56700 (11)	0.4650 (2)	0.0235 (4)
H36A	0.3559	0.5629	0.3436	0.035*
H36B	0.3776	0.6224	0.5001	0.035*
H36C	0.3262	0.5680	0.5039	0.035*

	U11	U22	U33	U12	U13	U23
O1	0.0235 (7)	0.0120 (7)	0.0356 (8)	−0.0005 (6)	−0.0020 (5)	0.0000 (6)
O2	0.0208 (6)	0.0277 (8)	0.0267 (7)	−0.0027 (6)	0.0036 (5)	−0.0061 (6)
O3	0.0244 (7)	0.0133 (7)	0.0288 (7)	0.0011 (6)	0.0003 (5)	−0.0011 (5)
N1	0.0169 (7)	0.0131 (8)	0.0200 (8)	0.0007 (6)	0.0000 (6)	0.0004 (6)
N2	0.0230 (8)	0.0126 (8)	0.0241 (8)	−0.0008 (7)	0.0020 (6)	−0.0007 (6)
N3	0.0212 (8)	0.0126 (8)	0.0285 (9)	0.0008 (7)	−0.0008 (7)	0.0017 (7)
C1	0.0200 (9)	0.0159 (10)	0.0138 (9)	−0.0008 (8)	0.0031 (7)	0.0000 (7)
C2	0.0206 (10)	0.0177 (10)	0.0205 (10)	−0.0011 (8)	0.0024 (7)	0.0003 (8)
C3	0.0187 (9)	0.0120 (9)	0.0196 (9)	−0.0007 (8)	−0.0008 (7)	0.0037 (7)
C4	0.0243 (10)	0.0133 (9)	0.0148 (9)	−0.0020 (8)	0.0001 (7)	0.0013 (7)
C5	0.0222 (9)	0.0148 (10)	0.0191 (9)	−0.0005 (8)	0.0006 (7)	0.0013 (8)
C6	0.0218 (9)	0.0200 (10)	0.0253 (10)	−0.0024 (8)	−0.0040 (8)	0.0010 (8)
C7	0.0293 (10)	0.0204 (11)	0.0183 (10)	0.0000 (9)	−0.0046 (8)	−0.0036 (8)
C8	0.0269 (10)	0.0151 (10)	0.0205 (10)	0.0009 (8)	0.0038 (8)	0.0003 (8)
C9	0.0265 (10)	0.0282 (12)	0.0276 (11)	−0.0013 (9)	0.0058 (8)	−0.0073 (9)
C10	0.0220 (9)	0.0150 (10)	0.0182 (9)	−0.0002 (8)	0.0027 (7)	−0.0005 (7)
C11	0.0228 (9)	0.0180 (10)	0.0188 (9)	0.0000 (8)	0.0023 (7)	−0.0017 (8)
C12	0.0221 (9)	0.0171 (10)	0.0112 (9)	−0.0003 (8)	0.0038 (7)	0.0010 (7)
C13	0.0225 (10)	0.0181 (10)	0.0191 (10)	−0.0044 (8)	0.0020 (7)	−0.0010 (8)
C14	0.0195 (9)	0.0193 (10)	0.0218 (10)	0.0014 (8)	0.0002 (7)	0.0008 (8)
C15	0.0240 (9)	0.0148 (10)	0.0122 (9)	0.0025 (8)	0.0035 (7)	0.0020 (7)
C16	0.0201 (9)	0.0194 (10)	0.0137 (9)	−0.0035 (8)	0.0006 (7)	−0.0005 (7)
C17	0.0204 (9)	0.0203 (10)	0.0162 (9)	0.0044 (8)	0.0026 (7)	0.0039 (8)
C18	0.0307 (10)	0.0154 (10)	0.0236 (10)	−0.0050 (9)	0.0025 (8)	−0.0023 (8)
O4	0.0222 (6)	0.0125 (7)	0.0346 (7)	0.0001 (6)	0.0016 (5)	−0.0010 (6)
O5	0.0186 (6)	0.0301 (8)	0.0274 (7)	−0.0001 (6)	0.0044 (5)	0.0034 (6)
O6	0.0244 (6)	0.0121 (7)	0.0264 (7)	0.0008 (5)	−0.0024 (5)	0.0000 (5)
N4	0.0168 (7)	0.0117 (8)	0.0219 (8)	0.0002 (6)	0.0029 (6)	−0.0008 (6)
N5	0.0220 (8)	0.0119 (8)	0.0263 (8)	−0.0005 (7)	0.0037 (6)	−0.0028 (7)
N6	0.0172 (8)	0.0130 (8)	0.0283 (9)	−0.0007 (7)	−0.0002 (7)	−0.0035 (7)
C19	0.0174 (9)	0.0148 (10)	0.0203 (9)	0.0018 (8)	0.0048 (7)	−0.0002 (8)
C20	0.0191 (9)	0.0168 (10)	0.0194 (9)	−0.0016 (8)	0.0056 (7)	−0.0016 (8)
C21	0.0171 (9)	0.0116 (9)	0.0193 (9)	−0.0007 (7)	0.0009 (7)	−0.0047 (7)
C22	0.0216 (9)	0.0127 (9)	0.0157 (9)	0.0013 (8)	0.0004 (7)	−0.0001 (7)
C23	0.0186 (9)	0.0139 (9)	0.0206 (9)	−0.0007 (8)	0.0027 (7)	−0.0051 (7)
C24	0.0207 (9)	0.0201 (10)	0.0234 (10)	0.0048 (8)	−0.0047 (8)	−0.0021 (8)
C25	0.0331 (11)	0.0190 (10)	0.0169 (9)	0.0008 (9)	−0.0017 (8)	0.0025 (8)
C26	0.0256 (10)	0.0181 (10)	0.0194 (10)	−0.0022 (8)	0.0038 (8)	−0.0005 (8)
C27	0.0273 (10)	0.0301 (12)	0.0270 (11)	−0.0023 (9)	0.0095 (8)	0.0062 (9)
C28	0.0198 (9)	0.0160 (10)	0.0216 (10)	−0.0002 (8)	0.0012 (7)	−0.0010 (8)
C29	0.0195 (9)	0.0176 (11)	0.0381 (11)	0.0006 (8)	0.0002 (8)	−0.0051 (9)
C30	0.0181 (9)	0.0142 (10)	0.0217 (10)	0.0013 (8)	0.0037 (7)	−0.0028 (8)
C31	0.0216 (9)	0.0147 (10)	0.0236 (10)	0.0038 (8)	0.0014 (7)	0.0017 (8)
C32	0.0188 (9)	0.0174 (10)	0.0212 (10)	−0.0010 (8)	−0.0023 (7)	−0.0004 (8)
C33	0.0204 (9)	0.0137 (9)	0.0161 (9)	−0.0033 (8)	0.0043 (7)	−0.0033 (7)
C34	0.0196 (9)	0.0154 (10)	0.0193 (9)	0.0041 (8)	0.0009 (7)	0.0017 (8)
C35	0.0174 (9)	0.0224 (11)	0.0192 (10)	−0.0004 (8)	−0.0009 (7)	−0.0016 (8)
C36	0.0317 (10)	0.0122 (10)	0.0260 (10)	0.0016 (8)	0.0005 (8)	0.0015 (8)

O1—C2	1.238 (2)	O4—C20	1.236 (2)
O2—C5	1.3656 (18)	O5—C23	1.3677 (18)
O2—C9	1.4248 (18)	O5—C27	1.4272 (19)
O3—C15	1.3786 (19)	O6—C33	1.3810 (19)
O3—C18	1.4292 (18)	O6—C36	1.4328 (19)
N1—C1	1.390 (2)	N4—C19	1.387 (2)
N1—C2	1.392 (2)	N4—C20	1.387 (2)
N1—C3	1.4323 (19)	N4—C21	1.4354 (19)
N2—C1	1.2955 (19)	N5—C19	1.2971 (19)
N2—N3	1.3871 (19)	N5—N6	1.3947 (18)
N3—C2	1.342 (2)	N6—C20	1.343 (2)
N3—H3N	0.972 (18)	N6—H6N	0.931 (16)
C1—C10	1.488 (2)	C19—C28	1.486 (2)
C3—C8	1.385 (2)	C21—C26	1.382 (2)
C3—C4	1.388 (2)	C21—C22	1.390 (2)
C4—C5	1.384 (2)	C22—C23	1.381 (2)
C4—H4	0.9500	C22—H22	0.9500
C5—C6	1.392 (2)	C23—C24	1.394 (2)
C6—C7	1.377 (2)	C24—C25	1.377 (2)
C6—H6	0.9500	C24—H24	0.9500
C7—C8	1.386 (2)	C25—C26	1.383 (2)
C7—H7	0.9500	C25—H25	0.9500
C8—H8	0.9500	C26—H26	0.9500
C9—H9A	0.9800	C27—H27A	0.9800
C9—H9B	0.9800	C27—H27B	0.9800
C9—H9C	0.9800	C27—H27C	0.9800
C10—C11	1.528 (2)	C28—C29	1.508 (2)
C10—H10A	0.9900	C28—H28A	0.9900
C10—H10B	0.9900	C28—H28B	0.9900
C11—C12	1.518 (2)	C29—C30	1.510 (2)
C11—H11A	0.9900	C29—H29A	0.9900
C11—H11B	0.9900	C29—H29B	0.9900
C12—C13	1.383 (2)	C30—C31	1.385 (2)
C12—C17	1.389 (2)	C30—C35	1.386 (2)
C13—C14	1.385 (2)	C31—C32	1.385 (2)
C13—H13	0.9500	C31—H31	0.9500
C14—C15	1.388 (2)	C32—C33	1.387 (2)
C14—H14	0.9500	C32—H32	0.9500
C15—C16	1.381 (2)	C33—C34	1.381 (2)
C16—C17	1.391 (2)	C34—C35	1.388 (2)
C16—H16	0.9500	C34—H34	0.9500
C17—H17	0.9500	C35—H35	0.9500
C18—H18A	0.9800	C36—H36A	0.9800
C18—H18B	0.9800	C36—H36B	0.9800
C18—H18C	0.9800	C36—H36C	0.9800
C5—O2—C9	117.80 (12)	C23—O5—C27	117.02 (12)
C15—O3—C18	117.49 (12)	C33—O6—C36	116.64 (12)
C1—N1—C2	107.42 (13)	C19—N4—C20	107.44 (13)
C1—N1—C3	128.95 (14)	C19—N4—C21	128.77 (14)
C2—N1—C3	123.41 (14)	C20—N4—C21	123.53 (14)
C1—N2—N3	104.94 (14)	C19—N5—N6	104.34 (13)
C2—N3—N2	112.82 (14)	C20—N6—N5	112.79 (13)
C2—N3—H3N	124.9 (11)	C20—N6—H6N	126.3 (11)
N2—N3—H3N	121.2 (11)	N5—N6—H6N	120.7 (11)
N2—C1—N1	110.98 (15)	N5—C19—N4	111.47 (15)
N2—C1—C10	122.56 (15)	N5—C19—C28	125.42 (15)
N1—C1—C10	126.46 (14)	N4—C19—C28	123.08 (14)
O1—C2—N3	128.76 (16)	O4—C20—N6	129.45 (16)
O1—C2—N1	127.46 (15)	O4—C20—N4	126.59 (15)
N3—C2—N1	103.78 (14)	N6—C20—N4	103.95 (14)
C8—C3—C4	121.78 (15)	C26—C21—C22	121.84 (15)
C8—C3—N1	119.09 (14)	C26—C21—N4	119.46 (15)
C4—C3—N1	119.09 (14)	C22—C21—N4	118.64 (14)
C5—C4—C3	118.80 (15)	C23—C22—C21	118.69 (15)
C5—C4—H4	120.6	C23—C22—H22	120.7
C3—C4—H4	120.6	C21—C22—H22	120.7
O2—C5—C4	124.17 (15)	O5—C23—C22	124.15 (15)
O2—C5—C6	115.64 (14)	O5—C23—C24	115.53 (14)
C4—C5—C6	120.16 (16)	C22—C23—C24	120.28 (15)
C7—C6—C5	119.97 (16)	C25—C24—C23	119.69 (15)
C7—C6—H6	120.0	C25—C24—H24	120.2
C5—C6—H6	120.0	C23—C24—H24	120.2
C6—C7—C8	120.93 (16)	C24—C25—C26	121.12 (16)
C6—C7—H7	119.5	C24—C25—H25	119.4
C8—C7—H7	119.5	C26—C25—H25	119.4
C3—C8—C7	118.34 (16)	C25—C26—C21	118.37 (16)
C3—C8—H8	120.8	C25—C26—H26	120.8
C7—C8—H8	120.8	C21—C26—H26	120.8
O2—C9—H9A	109.5	O5—C27—H27A	109.5
O2—C9—H9B	109.5	O5—C27—H27B	109.5
H9A—C9—H9B	109.5	H27A—C27—H27B	109.5
O2—C9—H9C	109.5	O5—C27—H27C	109.5
H9A—C9—H9C	109.5	H27A—C27—H27C	109.5
H9B—C9—H9C	109.5	H27B—C27—H27C	109.5
C1—C10—C11	116.39 (14)	C19—C28—C29	112.07 (13)
C1—C10—H10A	108.2	C19—C28—H28A	109.2
C11—C10—H10A	108.2	C29—C28—H28A	109.2
C1—C10—H10B	108.2	C19—C28—H28B	109.2
C11—C10—H10B	108.2	C29—C28—H28B	109.2
H10A—C10—H10B	107.3	H28A—C28—H28B	107.9
C12—C11—C10	110.39 (13)	C28—C29—C30	115.81 (13)
C12—C11—H11A	109.6	C28—C29—H29A	108.3
C10—C11—H11A	109.6	C30—C29—H29A	108.3
C12—C11—H11B	109.6	C28—C29—H29B	108.3
C10—C11—H11B	109.6	C30—C29—H29B	108.3
H11A—C11—H11B	108.1	H29A—C29—H29B	107.4
C13—C12—C17	117.66 (16)	C31—C30—C35	117.32 (16)
C13—C12—C11	121.60 (15)	C31—C30—C29	123.49 (15)
C17—C12—C11	120.68 (14)	C35—C30—C29	119.19 (14)
C12—C13—C14	121.03 (16)	C30—C31—C32	121.21 (16)
C12—C13—H13	119.5	C30—C31—H31	119.4
C14—C13—H13	119.5	C32—C31—H31	119.4
C13—C14—C15	120.43 (15)	C31—C32—C33	119.94 (15)
C13—C14—H14	119.8	C31—C32—H32	120.0
C15—C14—H14	119.8	C33—C32—H32	120.0
O3—C15—C16	125.02 (15)	C34—C33—O6	124.08 (15)
O3—C15—C14	115.36 (14)	C34—C33—C32	120.34 (16)
C16—C15—C14	119.60 (16)	O6—C33—C32	115.58 (14)
C15—C16—C17	119.05 (16)	C33—C34—C35	118.32 (16)
C15—C16—H16	120.5	C33—C34—H34	120.8
C17—C16—H16	120.5	C35—C34—H34	120.8
C12—C17—C16	122.20 (15)	C30—C35—C34	122.85 (15)
C12—C17—H17	118.9	C30—C35—H35	118.6
C16—C17—H17	118.9	C34—C35—H35	118.6
O3—C18—H18A	109.5	O6—C36—H36A	109.5
O3—C18—H18B	109.5	O6—C36—H36B	109.5
H18A—C18—H18B	109.5	H36A—C36—H36B	109.5
O3—C18—H18C	109.5	O6—C36—H36C	109.5
H18A—C18—H18C	109.5	H36A—C36—H36C	109.5
H18B—C18—H18C	109.5	H36B—C36—H36C	109.5
C1—N2—N3—C2	1.75 (19)	C19—N5—N6—C20	−0.04 (18)
N3—N2—C1—N1	−0.14 (17)	N6—N5—C19—N4	−0.11 (18)
N3—N2—C1—C10	−179.76 (14)	N6—N5—C19—C28	−178.32 (15)
C2—N1—C1—N2	−1.41 (18)	C20—N4—C19—N5	0.22 (18)
C3—N1—C1—N2	−176.04 (14)	C21—N4—C19—N5	174.33 (14)
C2—N1—C1—C10	178.19 (15)	C20—N4—C19—C28	178.48 (14)
C3—N1—C1—C10	3.6 (3)	C21—N4—C19—C28	−7.4 (2)
N2—N3—C2—O1	176.86 (16)	N5—N6—C20—O4	−179.34 (16)
N2—N3—C2—N1	−2.54 (18)	N5—N6—C20—N4	0.17 (18)
C1—N1—C2—O1	−177.09 (17)	C19—N4—C20—O4	179.31 (16)
C3—N1—C2—O1	−2.1 (3)	C21—N4—C20—O4	4.8 (3)
C1—N1—C2—N3	2.33 (17)	C19—N4—C20—N6	−0.23 (16)
C3—N1—C2—N3	177.33 (13)	C21—N4—C20—N6	−174.72 (13)
C1—N1—C3—C8	−125.99 (18)	C19—N4—C21—C26	121.19 (18)
C2—N1—C3—C8	60.1 (2)	C20—N4—C21—C26	−65.6 (2)
C1—N1—C3—C4	56.1 (2)	C19—N4—C21—C22	−61.6 (2)
C2—N1—C3—C4	−117.72 (18)	C20—N4—C21—C22	111.66 (18)
C8—C3—C4—C5	1.4 (2)	C26—C21—C22—C23	0.5 (2)
N1—C3—C4—C5	179.21 (14)	N4—C21—C22—C23	−176.62 (14)
C9—O2—C5—C4	6.1 (2)	C27—O5—C23—C22	−5.2 (2)
C9—O2—C5—C6	−172.28 (15)	C27—O5—C23—C24	172.59 (15)
C3—C4—C5—O2	−179.94 (15)	C21—C22—C23—O5	177.57 (15)
C3—C4—C5—C6	−1.6 (2)	C21—C22—C23—C24	−0.1 (2)
O2—C5—C6—C7	179.35 (15)	O5—C23—C24—C25	−178.55 (15)
C4—C5—C6—C7	0.9 (3)	C22—C23—C24—C25	−0.7 (3)
C5—C6—C7—C8	0.1 (3)	C23—C24—C25—C26	1.1 (3)
C4—C3—C8—C7	−0.4 (2)	C24—C25—C26—C21	−0.7 (3)
N1—C3—C8—C7	−178.24 (15)	C22—C21—C26—C25	−0.1 (3)
C6—C7—C8—C3	−0.3 (3)	N4—C21—C26—C25	176.97 (15)
N2—C1—C10—C11	−104.32 (18)	N5—C19—C28—C29	5.5 (2)
N1—C1—C10—C11	76.1 (2)	N4—C19—C28—C29	−172.56 (15)
C1—C10—C11—C12	167.77 (14)	C19—C28—C29—C30	−173.76 (14)
C10—C11—C12—C13	103.80 (17)	C28—C29—C30—C31	−19.9 (2)
C10—C11—C12—C17	−73.44 (18)	C28—C29—C30—C35	160.65 (15)
C17—C12—C13—C14	0.6 (2)	C35—C30—C31—C32	−0.6 (2)
C11—C12—C13—C14	−176.69 (15)	C29—C30—C31—C32	179.94 (15)
C12—C13—C14—C15	−1.3 (2)	C30—C31—C32—C33	1.8 (2)
C18—O3—C15—C16	−2.5 (2)	C36—O6—C33—C34	−1.8 (2)
C18—O3—C15—C14	176.08 (13)	C36—O6—C33—C32	178.02 (14)
C13—C14—C15—O3	−177.57 (14)	C31—C32—C33—C34	−1.8 (2)
C13—C14—C15—C16	1.1 (2)	C31—C32—C33—O6	178.34 (14)
O3—C15—C16—C17	178.24 (15)	O6—C33—C34—C35	−179.42 (14)
C14—C15—C16—C17	−0.3 (2)	C32—C33—C34—C35	0.8 (2)
C13—C12—C17—C16	0.2 (2)	C31—C30—C35—C34	−0.5 (2)
C11—C12—C17—C16	177.54 (15)	C29—C30—C35—C34	179.00 (15)
C15—C16—C17—C12	−0.3 (2)	C33—C34—C35—C30	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O4i	0.972 (18)	1.784 (19)	2.7463 (18)	169.6 (17)
N6—H6N···O1ii	0.931 (16)	1.936 (17)	2.8429 (18)	164.2 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O4i	0.972 (18)	1.784 (19)	2.7463 (18)	169.6 (17)
N6—H6N⋯O1ii	0.931 (16)	1.936 (17)	2.8429 (18)	164.2 (16)

Symmetry codes: (i) ; (ii) .