1-{2-[(4-Chloro-benzyl-idene)amino]phen-yl}-3-phenyl-thio-urea.

The asymmetric unit of the title compound, C(20)H(16)ClN(3)S, contains two independent mol-ecules, A and B. In mol-ecule A, the dihedral angles between the central benzene ring and the pendant chloro-benzene and phenyl rings are 6.37 (15) and 64.79 (15)°, respectively. The corresponding values in mol-ecule B are 28.21 (14) and 82.11 (16)°, respectively. Each mol-ecule features an intra-molecular N-H⋯N hydrogen bond, which generates an S(5) ring. In the crystal, mol-ecules A and B form dimers, being linked by two N-H⋯S hydrogen bonds with graph-set notation R(2) (2)(8).

Related literature

For background to the coordination chemistry of Schiff bases, see: Chen et al. (2010 ▶); Cui et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H16ClN3S

M = 365.87

Monoclinic,

a = 9.410 (3) Å

b = 23.079 (3) Å

c = 16.807 (2) Å

β = 100.226 (2)°

V = 3592.0 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.34 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.945, T max = 0.951

25609 measured reflections

6680 independent reflections

4051 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.117

S = 1.00

6680 reflections

463 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812006228/hb6632sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006228/hb6632Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006228/hb6632Isup3.cml

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

C20H16ClN3S	F(000) = 1520
Mr = 365.87	Dx = 1.353 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.410 (3) Å	Cell parameters from 4472 reflections
b = 23.079 (3) Å	θ = 2.4–24.5°
c = 16.807 (2) Å	µ = 0.34 mm−1
β = 100.226 (2)°	T = 298 K
V = 3592.0 (13) Å3	Block, yellow
Z = 8	0.17 × 0.15 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	6680 independent reflections
Radiation source: fine-focus sealed tube	4051 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.945, Tmax = 0.951	k = −27→26
25609 measured reflections	l = −20→20

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0334P)2 + 1.8733P] where P = (Fo2 + 2Fc2)/3
6680 reflections	(Δ/σ)max < 0.001
463 parameters	Δρmax = 0.31 e Å−3
4 restraints	Δρmin = −0.27 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
Cl1	0.63112 (12)	0.39717 (5)	−0.02622 (6)	0.0897 (3)
Cl2	0.63346 (9)	0.20059 (4)	0.47794 (5)	0.0672 (3)
N1	0.2757 (2)	0.37248 (10)	0.28692 (14)	0.0453 (6)
N2	0.1379 (3)	0.28279 (10)	0.32759 (15)	0.0494 (6)
N3	0.1149 (3)	0.19376 (10)	0.27030 (15)	0.0496 (6)
N4	0.2947 (2)	0.10566 (9)	0.77336 (13)	0.0396 (6)
N5	0.2405 (3)	−0.00077 (10)	0.81666 (14)	0.0462 (6)
N6	0.2450 (3)	−0.08378 (10)	0.74386 (17)	0.0540 (7)
S1	−0.09328 (8)	0.21834 (4)	0.34837 (5)	0.0560 (2)
S2	0.03254 (10)	−0.07857 (4)	0.82505 (5)	0.0639 (3)
C1	0.4126 (3)	0.40775 (12)	0.18976 (17)	0.0421 (7)
C2	0.4179 (3)	0.35595 (13)	0.14910 (18)	0.0509 (8)
H2A	0.3767	0.3230	0.1673	0.061*
C3	0.4832 (3)	0.35242 (14)	0.08212 (19)	0.0573 (9)
H3A	0.4857	0.3174	0.0549	0.069*
C4	0.5446 (3)	0.40117 (15)	0.05601 (18)	0.0549 (8)
C5	0.5406 (3)	0.45284 (14)	0.09521 (19)	0.0584 (9)
H5A	0.5830	0.4856	0.0772	0.070*
C6	0.4738 (3)	0.45629 (13)	0.16128 (18)	0.0532 (8)
H6A	0.4697	0.4917	0.1872	0.064*
C7	0.3428 (3)	0.41324 (12)	0.25979 (17)	0.0453 (7)
H7	0.3477	0.4488	0.2862	0.054*
C8	0.2020 (3)	0.38065 (13)	0.35255 (17)	0.0448 (7)
C9	0.1256 (3)	0.33273 (12)	0.37331 (17)	0.0441 (7)
C10	0.0506 (3)	0.33636 (14)	0.43690 (19)	0.0599 (9)
H10	0.0021	0.3042	0.4519	0.072*
C11	0.0481 (4)	0.38780 (16)	0.4776 (2)	0.0720 (11)
H11	−0.0041	0.3904	0.5196	0.086*
C12	0.1207 (4)	0.43513 (16)	0.4576 (2)	0.0707 (10)
H12	0.1178	0.4697	0.4856	0.085*
C13	0.1980 (3)	0.43156 (14)	0.3960 (2)	0.0620 (9)
H13	0.2487	0.4638	0.3831	0.074*
C14	0.0607 (3)	0.23353 (12)	0.31572 (16)	0.0430 (7)
C15	0.2432 (3)	0.19785 (11)	0.23773 (18)	0.0420 (7)
C16	0.3757 (3)	0.20611 (12)	0.2862 (2)	0.0533 (8)
H16	0.3822	0.2106	0.3417	0.064*
C17	0.4981 (3)	0.20764 (13)	0.2527 (2)	0.0611 (9)
H17	0.5875	0.2136	0.2854	0.073*
C18	0.4892 (4)	0.20044 (13)	0.1708 (2)	0.0623 (10)
H18	0.5725	0.2014	0.1482	0.075*
C19	0.3582 (4)	0.19191 (14)	0.1227 (2)	0.0619 (9)
H19	0.3525	0.1867	0.0673	0.074*
C20	0.2348 (3)	0.19091 (13)	0.15560 (18)	0.0519 (8)
H20	0.1455	0.1856	0.1225	0.062*
C21	0.5270 (3)	0.18491 (13)	0.54944 (16)	0.0462 (7)
C22	0.5486 (3)	0.13397 (13)	0.59180 (17)	0.0492 (8)
H22	0.6169	0.1074	0.5808	0.059*
C23	0.4681 (3)	0.12249 (12)	0.65079 (16)	0.0438 (7)
H23	0.4824	0.0880	0.6798	0.053*
C24	0.3664 (3)	0.16162 (12)	0.66733 (16)	0.0410 (7)
C25	0.3474 (3)	0.21226 (13)	0.62326 (19)	0.0581 (9)
H25	0.2795	0.2391	0.6340	0.070*
C26	0.4263 (3)	0.22396 (14)	0.56382 (19)	0.0578 (9)
H26	0.4112	0.2580	0.5339	0.069*
C27	0.2832 (3)	0.15137 (12)	0.73111 (16)	0.0435 (7)
H27	0.2186	0.1797	0.7413	0.052*
C28	0.2163 (3)	0.10037 (11)	0.83720 (16)	0.0371 (6)
C29	0.1911 (3)	0.04411 (11)	0.86153 (16)	0.0393 (7)
C30	0.1266 (3)	0.03522 (13)	0.92816 (17)	0.0515 (8)
H30	0.1132	−0.0022	0.9458	0.062*
C31	0.0822 (3)	0.08202 (14)	0.96840 (18)	0.0593 (9)
H31	0.0378	0.0760	1.0129	0.071*
C32	0.1031 (3)	0.13720 (14)	0.94326 (18)	0.0578 (9)
H32	0.0704	0.1685	0.9699	0.069*
C33	0.1717 (3)	0.14676 (12)	0.87925 (17)	0.0480 (8)
H33	0.1885	0.1845	0.8638	0.058*
C34	0.1802 (3)	−0.05245 (12)	0.79539 (17)	0.0440 (7)
C35	0.3686 (4)	−0.06772 (12)	0.7116 (2)	0.0520 (8)
C36	0.4987 (4)	−0.05871 (14)	0.7615 (3)	0.0716 (10)
H36	0.5053	−0.0612	0.8173	0.086*
C37	0.6190 (4)	−0.04602 (17)	0.7293 (4)	0.1041 (17)
H37	0.7072	−0.0399	0.7630	0.125*
C38	0.6087 (6)	−0.0425 (2)	0.6481 (4)	0.130 (2)
H38	0.6904	−0.0338	0.6264	0.155*
C39	0.4806 (7)	−0.0514 (2)	0.5980 (3)	0.121 (2)
H39	0.4747	−0.0489	0.5423	0.145*
C40	0.3587 (4)	−0.06431 (15)	0.6302 (2)	0.0791 (11)
H40	0.2706	−0.0706	0.5963	0.095*
H3	0.056 (3)	0.1640 (10)	0.2513 (18)	0.080*
H5	0.306 (3)	0.0129 (13)	0.7888 (17)	0.080*
H2	0.206 (3)	0.2887 (14)	0.2977 (16)	0.080*
H6	0.196 (3)	−0.1152 (9)	0.7242 (18)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.1045 (8)	0.1059 (8)	0.0690 (6)	−0.0180 (6)	0.0435 (6)	0.0027 (6)
Cl2	0.0719 (6)	0.0827 (6)	0.0542 (5)	−0.0080 (5)	0.0309 (4)	0.0078 (4)
N1	0.0449 (15)	0.0425 (15)	0.0515 (15)	−0.0055 (12)	0.0168 (12)	−0.0050 (12)
N2	0.0490 (16)	0.0439 (15)	0.0614 (17)	−0.0128 (13)	0.0268 (13)	−0.0102 (13)
N3	0.0427 (16)	0.0472 (16)	0.0636 (17)	−0.0115 (12)	0.0223 (13)	−0.0136 (13)
N4	0.0411 (14)	0.0353 (13)	0.0456 (14)	−0.0071 (11)	0.0169 (11)	−0.0012 (11)
N5	0.0530 (16)	0.0330 (14)	0.0586 (16)	−0.0110 (12)	0.0263 (13)	−0.0028 (12)
N6	0.0528 (17)	0.0396 (15)	0.0752 (18)	−0.0098 (12)	0.0266 (15)	−0.0134 (13)
S1	0.0452 (5)	0.0555 (5)	0.0733 (6)	−0.0057 (4)	0.0265 (4)	−0.0005 (4)
S2	0.0714 (6)	0.0557 (5)	0.0735 (6)	−0.0298 (4)	0.0366 (5)	−0.0149 (4)
C1	0.0356 (17)	0.0412 (17)	0.0486 (18)	−0.0033 (13)	0.0048 (14)	0.0014 (14)
C2	0.0507 (19)	0.0415 (18)	0.064 (2)	−0.0044 (15)	0.0194 (16)	0.0037 (15)
C3	0.059 (2)	0.053 (2)	0.063 (2)	−0.0094 (16)	0.0191 (18)	−0.0069 (16)
C4	0.053 (2)	0.065 (2)	0.0474 (19)	−0.0069 (17)	0.0125 (16)	0.0057 (17)
C5	0.061 (2)	0.056 (2)	0.059 (2)	−0.0158 (17)	0.0102 (18)	0.0096 (17)
C6	0.055 (2)	0.0438 (19)	0.060 (2)	−0.0093 (15)	0.0083 (17)	−0.0033 (16)
C7	0.0435 (18)	0.0360 (17)	0.0564 (19)	−0.0006 (14)	0.0091 (15)	−0.0045 (14)
C8	0.0413 (18)	0.0467 (18)	0.0480 (18)	−0.0018 (14)	0.0120 (15)	−0.0066 (14)
C9	0.0405 (17)	0.0468 (18)	0.0468 (17)	−0.0014 (14)	0.0123 (14)	−0.0083 (14)
C10	0.063 (2)	0.062 (2)	0.062 (2)	−0.0146 (17)	0.0292 (18)	−0.0150 (17)
C11	0.072 (2)	0.084 (3)	0.068 (2)	−0.015 (2)	0.035 (2)	−0.031 (2)
C12	0.073 (3)	0.067 (2)	0.079 (3)	−0.008 (2)	0.031 (2)	−0.031 (2)
C13	0.063 (2)	0.053 (2)	0.075 (2)	−0.0098 (17)	0.0256 (19)	−0.0158 (18)
C14	0.0417 (18)	0.0441 (18)	0.0446 (17)	−0.0018 (14)	0.0115 (14)	0.0039 (14)
C15	0.0366 (17)	0.0357 (16)	0.0560 (19)	−0.0053 (13)	0.0143 (15)	−0.0076 (14)
C16	0.043 (2)	0.0516 (19)	0.065 (2)	−0.0057 (15)	0.0072 (17)	−0.0106 (16)
C17	0.0367 (19)	0.051 (2)	0.093 (3)	−0.0062 (15)	0.0049 (18)	−0.0107 (19)
C18	0.048 (2)	0.048 (2)	0.099 (3)	−0.0031 (16)	0.038 (2)	−0.0011 (19)
C19	0.066 (2)	0.063 (2)	0.064 (2)	0.0006 (19)	0.032 (2)	−0.0002 (18)
C20	0.0467 (19)	0.056 (2)	0.054 (2)	−0.0030 (16)	0.0122 (16)	−0.0037 (16)
C21	0.0452 (19)	0.057 (2)	0.0398 (17)	−0.0072 (15)	0.0155 (14)	0.0023 (15)
C22	0.0450 (19)	0.058 (2)	0.0459 (18)	0.0050 (15)	0.0110 (15)	0.0004 (15)
C23	0.0439 (18)	0.0454 (17)	0.0425 (17)	−0.0005 (14)	0.0085 (14)	0.0069 (14)
C24	0.0415 (17)	0.0419 (17)	0.0412 (16)	−0.0080 (14)	0.0120 (14)	0.0021 (13)
C25	0.063 (2)	0.0445 (18)	0.074 (2)	0.0083 (16)	0.0326 (18)	0.0138 (17)
C26	0.065 (2)	0.050 (2)	0.063 (2)	−0.0006 (17)	0.0235 (18)	0.0198 (16)
C27	0.0451 (18)	0.0389 (17)	0.0493 (18)	−0.0029 (14)	0.0161 (15)	−0.0033 (14)
C28	0.0367 (16)	0.0363 (15)	0.0403 (16)	−0.0071 (12)	0.0125 (13)	−0.0022 (13)
C29	0.0389 (17)	0.0374 (16)	0.0433 (16)	−0.0092 (13)	0.0118 (14)	−0.0025 (13)
C30	0.062 (2)	0.0483 (19)	0.0479 (18)	−0.0190 (16)	0.0195 (16)	−0.0002 (15)
C31	0.071 (2)	0.063 (2)	0.0509 (19)	−0.0208 (18)	0.0312 (18)	−0.0123 (17)
C32	0.068 (2)	0.054 (2)	0.057 (2)	−0.0108 (17)	0.0280 (18)	−0.0163 (16)
C33	0.058 (2)	0.0384 (17)	0.0521 (19)	−0.0102 (14)	0.0215 (16)	−0.0059 (14)
C34	0.0496 (19)	0.0340 (16)	0.0503 (18)	−0.0050 (14)	0.0138 (15)	0.0012 (14)
C35	0.053 (2)	0.0308 (16)	0.078 (2)	−0.0016 (15)	0.0276 (19)	−0.0131 (16)
C36	0.058 (2)	0.050 (2)	0.110 (3)	−0.0070 (18)	0.024 (2)	−0.012 (2)
C37	0.062 (3)	0.065 (3)	0.194 (5)	−0.013 (2)	0.048 (3)	−0.047 (3)
C38	0.127 (5)	0.089 (3)	0.206 (6)	−0.048 (3)	0.120 (5)	−0.074 (4)
C39	0.162 (5)	0.111 (4)	0.116 (4)	−0.053 (4)	0.096 (4)	−0.049 (3)
C40	0.091 (3)	0.072 (3)	0.083 (3)	−0.010 (2)	0.038 (2)	−0.021 (2)

Cl1—C4	1.726 (3)	C15—C20	1.378 (4)
Cl2—C21	1.733 (3)	C16—C17	1.370 (4)
N1—C7	1.262 (3)	C16—H16	0.9300
N1—C8	1.416 (3)	C17—C18	1.374 (4)
N2—C14	1.345 (3)	C17—H17	0.9300
N2—C9	1.401 (3)	C18—C19	1.363 (4)
N2—H2	0.896 (10)	C18—H18	0.9300
N3—C14	1.350 (3)	C19—C20	1.373 (4)
N3—C15	1.415 (3)	C19—H19	0.9300
N3—H3	0.905 (10)	C20—H20	0.9300
N4—C27	1.266 (3)	C21—C26	1.360 (4)
N4—C28	1.411 (3)	C21—C22	1.371 (4)
N5—C34	1.342 (3)	C22—C23	1.376 (4)
N5—C29	1.408 (3)	C22—H22	0.9300
N5—H5	0.895 (10)	C23—C24	1.380 (4)
N6—C34	1.354 (3)	C23—H23	0.9300
N6—C35	1.416 (4)	C24—C25	1.378 (4)
N6—H6	0.892 (10)	C24—C27	1.454 (3)
S1—C14	1.675 (3)	C25—C26	1.374 (4)
S2—C34	1.670 (3)	C25—H25	0.9300
C1—C2	1.382 (4)	C26—H26	0.9300
C1—C6	1.384 (4)	C27—H27	0.9300
C1—C7	1.452 (4)	C28—C33	1.388 (4)
C2—C3	1.378 (4)	C28—C29	1.394 (3)
C2—H2A	0.9300	C29—C30	1.381 (3)
C3—C4	1.372 (4)	C30—C31	1.378 (4)
C3—H3A	0.9300	C30—H30	0.9300
C4—C5	1.366 (4)	C31—C32	1.367 (4)
C5—C6	1.372 (4)	C31—H31	0.9300
C5—H5A	0.9300	C32—C33	1.367 (4)
C6—H6A	0.9300	C32—H32	0.9300
C7—H7	0.9300	C33—H33	0.9300
C8—C13	1.388 (4)	C35—C40	1.357 (4)
C8—C9	1.397 (4)	C35—C36	1.371 (5)
C9—C10	1.384 (4)	C36—C37	1.370 (5)
C10—C11	1.373 (4)	C36—H36	0.9300
C10—H10	0.9300	C37—C38	1.352 (7)
C11—C12	1.363 (5)	C37—H37	0.9300
C11—H11	0.9300	C38—C39	1.359 (7)
C12—C13	1.369 (4)	C38—H38	0.9300
C12—H12	0.9300	C39—C40	1.385 (5)
C13—H13	0.9300	C39—H39	0.9300
C15—C16	1.376 (4)	C40—H40	0.9300
C7—N1—C8	121.8 (2)	C17—C18—H18	120.0
C14—N2—C9	133.0 (2)	C18—C19—C20	120.3 (3)
C14—N2—H2	118 (2)	C18—C19—H19	119.9
C9—N2—H2	109 (2)	C20—C19—H19	119.9
C14—N3—C15	127.4 (2)	C19—C20—C15	120.0 (3)
C14—N3—H3	117 (2)	C19—C20—H20	120.0
C15—N3—H3	115 (2)	C15—C20—H20	120.0
C27—N4—C28	119.7 (2)	C26—C21—C22	121.3 (3)
C34—N5—C29	129.2 (2)	C26—C21—Cl2	119.4 (2)
C34—N5—H5	118 (2)	C22—C21—Cl2	119.3 (2)
C29—N5—H5	110 (2)	C21—C22—C23	119.3 (3)
C34—N6—C35	126.8 (2)	C21—C22—H22	120.3
C34—N6—H6	114 (2)	C23—C22—H22	120.3
C35—N6—H6	119 (2)	C22—C23—C24	120.6 (3)
C2—C1—C6	118.4 (3)	C22—C23—H23	119.7
C2—C1—C7	122.5 (3)	C24—C23—H23	119.7
C6—C1—C7	119.1 (3)	C25—C24—C23	118.4 (3)
C3—C2—C1	121.1 (3)	C25—C24—C27	119.9 (3)
C3—C2—H2A	119.5	C23—C24—C27	121.7 (3)
C1—C2—H2A	119.5	C26—C25—C24	121.5 (3)
C4—C3—C2	119.2 (3)	C26—C25—H25	119.3
C4—C3—H3A	120.4	C24—C25—H25	119.3
C2—C3—H3A	120.4	C21—C26—C25	118.9 (3)
C5—C4—C3	120.8 (3)	C21—C26—H26	120.6
C5—C4—Cl1	119.4 (2)	C25—C26—H26	120.6
C3—C4—Cl1	119.8 (3)	N4—C27—C24	123.1 (3)
C4—C5—C6	119.8 (3)	N4—C27—H27	118.5
C4—C5—H5A	120.1	C24—C27—H27	118.5
C6—C5—H5A	120.1	C33—C28—C29	119.1 (2)
C5—C6—C1	120.8 (3)	C33—C28—N4	124.5 (2)
C5—C6—H6A	119.6	C29—C28—N4	116.3 (2)
C1—C6—H6A	119.6	C30—C29—C28	119.9 (3)
N1—C7—C1	123.7 (3)	C30—C29—N5	124.0 (2)
N1—C7—H7	118.1	C28—C29—N5	116.0 (2)
C1—C7—H7	118.1	C31—C30—C29	119.8 (3)
C13—C8—C9	118.4 (3)	C31—C30—H30	120.1
C13—C8—N1	125.9 (3)	C29—C30—H30	120.1
C9—C8—N1	115.7 (2)	C32—C31—C30	120.4 (3)
C10—C9—C8	120.0 (3)	C32—C31—H31	119.8
C10—C9—N2	125.2 (3)	C30—C31—H31	119.8
C8—C9—N2	114.7 (2)	C31—C32—C33	120.5 (3)
C11—C10—C9	119.6 (3)	C31—C32—H32	119.8
C11—C10—H10	120.2	C33—C32—H32	119.8
C9—C10—H10	120.2	C32—C33—C28	120.3 (3)
C12—C11—C10	121.0 (3)	C32—C33—H33	119.9
C12—C11—H11	119.5	C28—C33—H33	119.9
C10—C11—H11	119.5	N5—C34—N6	115.3 (2)
C11—C12—C13	119.8 (3)	N5—C34—S2	125.2 (2)
C11—C12—H12	120.1	N6—C34—S2	119.5 (2)
C13—C12—H12	120.1	C40—C35—C36	120.1 (3)
C12—C13—C8	121.1 (3)	C40—C35—N6	119.1 (3)
C12—C13—H13	119.4	C36—C35—N6	120.7 (3)
C8—C13—H13	119.4	C37—C36—C35	120.1 (4)
N2—C14—N3	114.2 (2)	C37—C36—H36	120.0
N2—C14—S1	127.2 (2)	C35—C36—H36	120.0
N3—C14—S1	118.6 (2)	C38—C37—C36	119.7 (5)
C16—C15—C20	119.6 (3)	C38—C37—H37	120.1
C16—C15—N3	121.7 (3)	C36—C37—H37	120.1
C20—C15—N3	118.6 (3)	C37—C38—C39	120.8 (4)
C17—C16—C15	119.9 (3)	C37—C38—H38	119.6
C17—C16—H16	120.0	C39—C38—H38	119.6
C15—C16—H16	120.0	C38—C39—C40	119.7 (5)
C16—C17—C18	120.2 (3)	C38—C39—H39	120.1
C16—C17—H17	119.9	C40—C39—H39	120.1
C18—C17—H17	119.9	C35—C40—C39	119.5 (4)
C19—C18—C17	120.0 (3)	C35—C40—H40	120.2
C19—C18—H18	120.0	C39—C40—H40	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···S1i	0.89 (1)	2.77 (1)	3.647 (3)	168 (3)
N2—H2···N1	0.90 (1)	2.06 (3)	2.598 (3)	118 (3)
N5—H5···N4	0.90 (1)	2.16 (3)	2.637 (3)	113 (2)
N3—H3···S2i	0.91 (1)	2.42 (2)	3.282 (2)	160 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯S1i	0.89 (1)	2.77 (1)	3.647 (3)	168 (3)
N2—H2⋯N1	0.90 (1)	2.06 (3)	2.598 (3)	118 (3)
N5—H5⋯N4	0.90 (1)	2.16 (3)	2.637 (3)	113 (2)
N3—H3⋯S2i	0.91 (1)	2.42 (2)	3.282 (2)	160 (3)

Symmetry code: (i) .