1-{2-[(4-Chloro­benzyl­idene)amino]phen­yl}-3-phenyl­thio­urea

Liu, P.-G.; Wang, X.-N.; Yang, Y.-A.; Zhu, H.-L.

doi:10.1107/S1600536812006228

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o767

doi:10.1107/S1600536812006228

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1-{2-[(4-Chlorobenzylidene)amino]phenyl}-3-phenylthiourea

Peng-Gang Liu,^a Xiao-Ning Wang,^a Yong-An Yang ^a and Hai-Liang Zhu ^a ^*

^aState Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: hailiang_zhu@163.com

(Received 12 February 2012; accepted 12 February 2012; online 17 February 2012)

The asymmetric unit of the title compound, C₂₀H₁₆ClN₃S, contains two independent molecules, A and B. In molecule A, the dihedral angles between the central benzene ring and the pendant chlorobenzene and phenyl rings are 6.37 (15) and 64.79 (15)°, respectively. The corresponding values in molecule B are 28.21 (14) and 82.11 (16)°, respectively. Each molecule features an intramolecular N—H⋯N hydrogen bond, which generates an S(5) ring. In the crystal, molecules A and B form dimers, being linked by two N—H⋯S hydrogen bonds with graph-set notation R₂²(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_r = 365.87
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.117
S = 1.00
6680 reflections
463 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.27 e Å⁻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) -x, -y, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006228/hb6632sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812006228/hb6632Isup3.cml

checkCIF report

Comment top

Schiff bases are a kind of versatile ligands in the preparation of complexes (e.g. Chen et al., 2010; Cui et al., 2011). In the present paper, the title compound is reported.

There are two independent molecules, A and B, in the asymmetric unit of the title compound (Fig. 1). In A, the C8–C13 benzene ring forms dihedral angles of 6.1 (3) and 65.1 (3)° with the C1–C6 and C15–C20 benzene rings, respectively. The dihedral angle between the C1–C6 and C15–C20 benzene rings is 68.9 (3)°. In B, the C28–C33 benzene ring forms dihedral angles of 27.5 (3) and 82.8 (3)° with the C21–C26 and C35–C40 benzene rings, respectively. The dihedral angle between the C21–C26 and C35–C40 benzene rings is 70.6 (3)°. There forms an intramolecular N—H···N hydrogen bond in each molecule (Table 1).

Related literature top

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 top

o-Diaminobenzene from the plant Sophora Alopecuroides (1.85 mmol) was dissolved in ethanol (4 ml) and stirred at 293 K, a solution of phenyl isothiocyanate (0.22 ml) and ethanol was dropwised into the reaction mixture when the diaminobenzene was completely dissolved. The reaction mixture was stirred until the solids formed largely. The products were filtrated and washed carefully with EtOH; the resulting N-(2-amino)phenyl-N'-phenyl-thiourea were purified by crystallization from EtOH in refrigerator. N-(2-Amino)phenyl-N'-phenyl-thiourea (2.5 mmol) was dissolved in ethanol (10 ml) and stirred 353 K, salicylaldehyde (3.0 mmol) was dropwised into the solution when the solid was completely dissolved. The reaction mixture was stirred for 2.5 h. The product was filtrated timely and dried by vacuum. Yellow block-shaped single crystals were obtained by slow evaporation of the methanolic solution containing the compound in air.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. Intramolecular hydrogen bonds are indicated by dashed lines.
	Fig. 2. The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are indicated by dashed lines.

1-{2-[(4-Chlorobenzylidene)amino]phenyl}-3-phenylthiourea top

Crystal data top

C₂₀H₁₆ClN₃S	F(000) = 1520
M_r = 365.87	D_x = 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

Data collection top

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

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)] = 0.049	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(F_o²) + (0.0334P)² + 1.8733P] where P = (F_o² + 2F_c²)/3
6680 reflections	(Δ/σ)_max < 0.001
463 parameters	Δρ_max = 0.31 e Å⁻³
4 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₀H₁₆ClN₃S	V = 3592.0 (13) Å³
M_r = 365.87	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.410 (3) Å	µ = 0.34 mm⁻¹
b = 23.079 (3) Å	T = 298 K
c = 16.807 (2) Å	0.17 × 0.15 × 0.15 mm
β = 100.226 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6680 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4051 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.951	R_int = 0.064
25609 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	4 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.31 e Å⁻³
6680 reflections	Δρ_min = −0.27 e Å⁻³
463 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆ClN₃S
M_r	365.87
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.410 (3), 23.079 (3), 16.807 (2)
β (°)	100.226 (2)
V (Å³)	3592.0 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.945, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	25609, 6680, 4051
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.117, 1.00
No. of reflections	6680
No. of parameters	463
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.27

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···S1ⁱ	0.892 (10)	2.769 (12)	3.647 (3)	168 (3)
N2—H2···N1	0.896 (10)	2.06 (3)	2.598 (3)	118 (3)
N5—H5···N4	0.895 (10)	2.16 (3)	2.637 (3)	113 (2)
N3—H3···S2ⁱ	0.905 (10)	2.418 (15)	3.282 (2)	160 (3)

Symmetry code: (i) −x, −y, −z+1.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, W., Li, Y.-G., Cui, Y.-M., Zhang, X.-A., Zhu, H.-L. & Zeng, Q.-F. (2010). Eur. J. Med. Chem. 45, 4473–4478. Web of Science CSD CrossRef CAS PubMed Google Scholar
Cui, Y.-M., Li, Y.-G., Cai, Y.-J., Chen, W. & Zhu, H.-L. (2011). J. Coord. Chem. 64, 610–616. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Page o767

doi:10.1107/S1600536812006228

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