organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[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.]); Cui et al. (2011[Cui, Y.-M., Li, Y.-G., Cai, Y.-J., Chen, W. & Zhu, H.-L. (2011). J. Coord. Chem. 64, 610-616.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C20H16ClN3S

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.945, Tmax = 0.951

  • 25609 measured reflections

  • 6680 independent reflections

  • 4051 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

The amino H atoms were located from a difference Fourier map and refined isotropically, with the N—H distances restrained to 0.90 (1) Å, and with Uiso restrained to 0.08 Å2. Other H atoms were constrained to ideal geometries, with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C).

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
[Figure 1] 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.
[Figure 2] 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
C20H16ClN3SF(000) = 1520
Mr = 365.87Dx = 1.353 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.410 (3) ÅCell parameters from 4472 reflections
b = 23.079 (3) Åθ = 2.4–24.5°
c = 16.807 (2) ŵ = 0.34 mm1
β = 100.226 (2)°T = 298 K
V = 3592.0 (13) Å3Block, yellow
Z = 80.17 × 0.15 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
6680 independent reflections
Radiation source: fine-focus sealed tube4051 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ω scansθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.945, Tmax = 0.951k = 2726
25609 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H 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 parametersΔρmax = 0.31 e Å3
4 restraintsΔρmin = 0.27 e Å3
Crystal data top
C20H16ClN3SV = 3592.0 (13) Å3
Mr = 365.87Z = 8
Monoclinic, P21/nMo Kα radiation
a = 9.410 (3) ŵ = 0.34 mm1
b = 23.079 (3) ÅT = 298 K
c = 16.807 (2) Å0.17 × 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)
Tmin = 0.945, Tmax = 0.951Rint = 0.064
25609 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0494 restraints
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.31 e Å3
6680 reflectionsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
Cl10.63112 (12)0.39717 (5)0.02622 (6)0.0897 (3)
Cl20.63346 (9)0.20059 (4)0.47794 (5)0.0672 (3)
N10.2757 (2)0.37248 (10)0.28692 (14)0.0453 (6)
N20.1379 (3)0.28279 (10)0.32759 (15)0.0494 (6)
N30.1149 (3)0.19376 (10)0.27030 (15)0.0496 (6)
N40.2947 (2)0.10566 (9)0.77336 (13)0.0396 (6)
N50.2405 (3)0.00077 (10)0.81666 (14)0.0462 (6)
N60.2450 (3)0.08378 (10)0.74386 (17)0.0540 (7)
S10.09328 (8)0.21834 (4)0.34837 (5)0.0560 (2)
S20.03254 (10)0.07857 (4)0.82505 (5)0.0639 (3)
C10.4126 (3)0.40775 (12)0.18976 (17)0.0421 (7)
C20.4179 (3)0.35595 (13)0.14910 (18)0.0509 (8)
H2A0.37670.32300.16730.061*
C30.4832 (3)0.35242 (14)0.08212 (19)0.0573 (9)
H3A0.48570.31740.05490.069*
C40.5446 (3)0.40117 (15)0.05601 (18)0.0549 (8)
C50.5406 (3)0.45284 (14)0.09521 (19)0.0584 (9)
H5A0.58300.48560.07720.070*
C60.4738 (3)0.45629 (13)0.16128 (18)0.0532 (8)
H6A0.46970.49170.18720.064*
C70.3428 (3)0.41324 (12)0.25979 (17)0.0453 (7)
H70.34770.44880.28620.054*
C80.2020 (3)0.38065 (13)0.35255 (17)0.0448 (7)
C90.1256 (3)0.33273 (12)0.37331 (17)0.0441 (7)
C100.0506 (3)0.33636 (14)0.43690 (19)0.0599 (9)
H100.00210.30420.45190.072*
C110.0481 (4)0.38780 (16)0.4776 (2)0.0720 (11)
H110.00410.39040.51960.086*
C120.1207 (4)0.43513 (16)0.4576 (2)0.0707 (10)
H120.11780.46970.48560.085*
C130.1980 (3)0.43156 (14)0.3960 (2)0.0620 (9)
H130.24870.46380.38310.074*
C140.0607 (3)0.23353 (12)0.31572 (16)0.0430 (7)
C150.2432 (3)0.19785 (11)0.23773 (18)0.0420 (7)
C160.3757 (3)0.20611 (12)0.2862 (2)0.0533 (8)
H160.38220.21060.34170.064*
C170.4981 (3)0.20764 (13)0.2527 (2)0.0611 (9)
H170.58750.21360.28540.073*
C180.4892 (4)0.20044 (13)0.1708 (2)0.0623 (10)
H180.57250.20140.14820.075*
C190.3582 (4)0.19191 (14)0.1227 (2)0.0619 (9)
H190.35250.18670.06730.074*
C200.2348 (3)0.19091 (13)0.15560 (18)0.0519 (8)
H200.14550.18560.12250.062*
C210.5270 (3)0.18491 (13)0.54944 (16)0.0462 (7)
C220.5486 (3)0.13397 (13)0.59180 (17)0.0492 (8)
H220.61690.10740.58080.059*
C230.4681 (3)0.12249 (12)0.65079 (16)0.0438 (7)
H230.48240.08800.67980.053*
C240.3664 (3)0.16162 (12)0.66733 (16)0.0410 (7)
C250.3474 (3)0.21226 (13)0.62326 (19)0.0581 (9)
H250.27950.23910.63400.070*
C260.4263 (3)0.22396 (14)0.56382 (19)0.0578 (9)
H260.41120.25800.53390.069*
C270.2832 (3)0.15137 (12)0.73111 (16)0.0435 (7)
H270.21860.17970.74130.052*
C280.2163 (3)0.10037 (11)0.83720 (16)0.0371 (6)
C290.1911 (3)0.04411 (11)0.86153 (16)0.0393 (7)
C300.1266 (3)0.03522 (13)0.92816 (17)0.0515 (8)
H300.11320.00220.94580.062*
C310.0822 (3)0.08202 (14)0.96840 (18)0.0593 (9)
H310.03780.07601.01290.071*
C320.1031 (3)0.13720 (14)0.94326 (18)0.0578 (9)
H320.07040.16850.96990.069*
C330.1717 (3)0.14676 (12)0.87925 (17)0.0480 (8)
H330.18850.18450.86380.058*
C340.1802 (3)0.05245 (12)0.79539 (17)0.0440 (7)
C350.3686 (4)0.06772 (12)0.7116 (2)0.0520 (8)
C360.4987 (4)0.05871 (14)0.7615 (3)0.0716 (10)
H360.50530.06120.81730.086*
C370.6190 (4)0.04602 (17)0.7293 (4)0.1041 (17)
H370.70720.03990.76300.125*
C380.6087 (6)0.0425 (2)0.6481 (4)0.130 (2)
H380.69040.03380.62640.155*
C390.4806 (7)0.0514 (2)0.5980 (3)0.121 (2)
H390.47470.04890.54230.145*
C400.3587 (4)0.06431 (15)0.6302 (2)0.0791 (11)
H400.27060.07060.59630.095*
H30.056 (3)0.1640 (10)0.2513 (18)0.080*
H50.306 (3)0.0129 (13)0.7888 (17)0.080*
H20.206 (3)0.2887 (14)0.2977 (16)0.080*
H60.196 (3)0.1152 (9)0.7242 (18)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1045 (8)0.1059 (8)0.0690 (6)0.0180 (6)0.0435 (6)0.0027 (6)
Cl20.0719 (6)0.0827 (6)0.0542 (5)0.0080 (5)0.0309 (4)0.0078 (4)
N10.0449 (15)0.0425 (15)0.0515 (15)0.0055 (12)0.0168 (12)0.0050 (12)
N20.0490 (16)0.0439 (15)0.0614 (17)0.0128 (13)0.0268 (13)0.0102 (13)
N30.0427 (16)0.0472 (16)0.0636 (17)0.0115 (12)0.0223 (13)0.0136 (13)
N40.0411 (14)0.0353 (13)0.0456 (14)0.0071 (11)0.0169 (11)0.0012 (11)
N50.0530 (16)0.0330 (14)0.0586 (16)0.0110 (12)0.0263 (13)0.0028 (12)
N60.0528 (17)0.0396 (15)0.0752 (18)0.0098 (12)0.0266 (15)0.0134 (13)
S10.0452 (5)0.0555 (5)0.0733 (6)0.0057 (4)0.0265 (4)0.0005 (4)
S20.0714 (6)0.0557 (5)0.0735 (6)0.0298 (4)0.0366 (5)0.0149 (4)
C10.0356 (17)0.0412 (17)0.0486 (18)0.0033 (13)0.0048 (14)0.0014 (14)
C20.0507 (19)0.0415 (18)0.064 (2)0.0044 (15)0.0194 (16)0.0037 (15)
C30.059 (2)0.053 (2)0.063 (2)0.0094 (16)0.0191 (18)0.0069 (16)
C40.053 (2)0.065 (2)0.0474 (19)0.0069 (17)0.0125 (16)0.0057 (17)
C50.061 (2)0.056 (2)0.059 (2)0.0158 (17)0.0102 (18)0.0096 (17)
C60.055 (2)0.0438 (19)0.060 (2)0.0093 (15)0.0083 (17)0.0033 (16)
C70.0435 (18)0.0360 (17)0.0564 (19)0.0006 (14)0.0091 (15)0.0045 (14)
C80.0413 (18)0.0467 (18)0.0480 (18)0.0018 (14)0.0120 (15)0.0066 (14)
C90.0405 (17)0.0468 (18)0.0468 (17)0.0014 (14)0.0123 (14)0.0083 (14)
C100.063 (2)0.062 (2)0.062 (2)0.0146 (17)0.0292 (18)0.0150 (17)
C110.072 (2)0.084 (3)0.068 (2)0.015 (2)0.035 (2)0.031 (2)
C120.073 (3)0.067 (2)0.079 (3)0.008 (2)0.031 (2)0.031 (2)
C130.063 (2)0.053 (2)0.075 (2)0.0098 (17)0.0256 (19)0.0158 (18)
C140.0417 (18)0.0441 (18)0.0446 (17)0.0018 (14)0.0115 (14)0.0039 (14)
C150.0366 (17)0.0357 (16)0.0560 (19)0.0053 (13)0.0143 (15)0.0076 (14)
C160.043 (2)0.0516 (19)0.065 (2)0.0057 (15)0.0072 (17)0.0106 (16)
C170.0367 (19)0.051 (2)0.093 (3)0.0062 (15)0.0049 (18)0.0107 (19)
C180.048 (2)0.048 (2)0.099 (3)0.0031 (16)0.038 (2)0.0011 (19)
C190.066 (2)0.063 (2)0.064 (2)0.0006 (19)0.032 (2)0.0002 (18)
C200.0467 (19)0.056 (2)0.054 (2)0.0030 (16)0.0122 (16)0.0037 (16)
C210.0452 (19)0.057 (2)0.0398 (17)0.0072 (15)0.0155 (14)0.0023 (15)
C220.0450 (19)0.058 (2)0.0459 (18)0.0050 (15)0.0110 (15)0.0004 (15)
C230.0439 (18)0.0454 (17)0.0425 (17)0.0005 (14)0.0085 (14)0.0069 (14)
C240.0415 (17)0.0419 (17)0.0412 (16)0.0080 (14)0.0120 (14)0.0021 (13)
C250.063 (2)0.0445 (18)0.074 (2)0.0083 (16)0.0326 (18)0.0138 (17)
C260.065 (2)0.050 (2)0.063 (2)0.0006 (17)0.0235 (18)0.0198 (16)
C270.0451 (18)0.0389 (17)0.0493 (18)0.0029 (14)0.0161 (15)0.0033 (14)
C280.0367 (16)0.0363 (15)0.0403 (16)0.0071 (12)0.0125 (13)0.0022 (13)
C290.0389 (17)0.0374 (16)0.0433 (16)0.0092 (13)0.0118 (14)0.0025 (13)
C300.062 (2)0.0483 (19)0.0479 (18)0.0190 (16)0.0195 (16)0.0002 (15)
C310.071 (2)0.063 (2)0.0509 (19)0.0208 (18)0.0312 (18)0.0123 (17)
C320.068 (2)0.054 (2)0.057 (2)0.0108 (17)0.0280 (18)0.0163 (16)
C330.058 (2)0.0384 (17)0.0521 (19)0.0102 (14)0.0215 (16)0.0059 (14)
C340.0496 (19)0.0340 (16)0.0503 (18)0.0050 (14)0.0138 (15)0.0012 (14)
C350.053 (2)0.0308 (16)0.078 (2)0.0016 (15)0.0276 (19)0.0131 (16)
C360.058 (2)0.050 (2)0.110 (3)0.0070 (18)0.024 (2)0.012 (2)
C370.062 (3)0.065 (3)0.194 (5)0.013 (2)0.048 (3)0.047 (3)
C380.127 (5)0.089 (3)0.206 (6)0.048 (3)0.120 (5)0.074 (4)
C390.162 (5)0.111 (4)0.116 (4)0.053 (4)0.096 (4)0.049 (3)
C400.091 (3)0.072 (3)0.083 (3)0.010 (2)0.038 (2)0.021 (2)
Geometric parameters (Å, º) top
Cl1—C41.726 (3)C15—C201.378 (4)
Cl2—C211.733 (3)C16—C171.370 (4)
N1—C71.262 (3)C16—H160.9300
N1—C81.416 (3)C17—C181.374 (4)
N2—C141.345 (3)C17—H170.9300
N2—C91.401 (3)C18—C191.363 (4)
N2—H20.896 (10)C18—H180.9300
N3—C141.350 (3)C19—C201.373 (4)
N3—C151.415 (3)C19—H190.9300
N3—H30.905 (10)C20—H200.9300
N4—C271.266 (3)C21—C261.360 (4)
N4—C281.411 (3)C21—C221.371 (4)
N5—C341.342 (3)C22—C231.376 (4)
N5—C291.408 (3)C22—H220.9300
N5—H50.895 (10)C23—C241.380 (4)
N6—C341.354 (3)C23—H230.9300
N6—C351.416 (4)C24—C251.378 (4)
N6—H60.892 (10)C24—C271.454 (3)
S1—C141.675 (3)C25—C261.374 (4)
S2—C341.670 (3)C25—H250.9300
C1—C21.382 (4)C26—H260.9300
C1—C61.384 (4)C27—H270.9300
C1—C71.452 (4)C28—C331.388 (4)
C2—C31.378 (4)C28—C291.394 (3)
C2—H2A0.9300C29—C301.381 (3)
C3—C41.372 (4)C30—C311.378 (4)
C3—H3A0.9300C30—H300.9300
C4—C51.366 (4)C31—C321.367 (4)
C5—C61.372 (4)C31—H310.9300
C5—H5A0.9300C32—C331.367 (4)
C6—H6A0.9300C32—H320.9300
C7—H70.9300C33—H330.9300
C8—C131.388 (4)C35—C401.357 (4)
C8—C91.397 (4)C35—C361.371 (5)
C9—C101.384 (4)C36—C371.370 (5)
C10—C111.373 (4)C36—H360.9300
C10—H100.9300C37—C381.352 (7)
C11—C121.363 (5)C37—H370.9300
C11—H110.9300C38—C391.359 (7)
C12—C131.369 (4)C38—H380.9300
C12—H120.9300C39—C401.385 (5)
C13—H130.9300C39—H390.9300
C15—C161.376 (4)C40—H400.9300
C7—N1—C8121.8 (2)C17—C18—H18120.0
C14—N2—C9133.0 (2)C18—C19—C20120.3 (3)
C14—N2—H2118 (2)C18—C19—H19119.9
C9—N2—H2109 (2)C20—C19—H19119.9
C14—N3—C15127.4 (2)C19—C20—C15120.0 (3)
C14—N3—H3117 (2)C19—C20—H20120.0
C15—N3—H3115 (2)C15—C20—H20120.0
C27—N4—C28119.7 (2)C26—C21—C22121.3 (3)
C34—N5—C29129.2 (2)C26—C21—Cl2119.4 (2)
C34—N5—H5118 (2)C22—C21—Cl2119.3 (2)
C29—N5—H5110 (2)C21—C22—C23119.3 (3)
C34—N6—C35126.8 (2)C21—C22—H22120.3
C34—N6—H6114 (2)C23—C22—H22120.3
C35—N6—H6119 (2)C22—C23—C24120.6 (3)
C2—C1—C6118.4 (3)C22—C23—H23119.7
C2—C1—C7122.5 (3)C24—C23—H23119.7
C6—C1—C7119.1 (3)C25—C24—C23118.4 (3)
C3—C2—C1121.1 (3)C25—C24—C27119.9 (3)
C3—C2—H2A119.5C23—C24—C27121.7 (3)
C1—C2—H2A119.5C26—C25—C24121.5 (3)
C4—C3—C2119.2 (3)C26—C25—H25119.3
C4—C3—H3A120.4C24—C25—H25119.3
C2—C3—H3A120.4C21—C26—C25118.9 (3)
C5—C4—C3120.8 (3)C21—C26—H26120.6
C5—C4—Cl1119.4 (2)C25—C26—H26120.6
C3—C4—Cl1119.8 (3)N4—C27—C24123.1 (3)
C4—C5—C6119.8 (3)N4—C27—H27118.5
C4—C5—H5A120.1C24—C27—H27118.5
C6—C5—H5A120.1C33—C28—C29119.1 (2)
C5—C6—C1120.8 (3)C33—C28—N4124.5 (2)
C5—C6—H6A119.6C29—C28—N4116.3 (2)
C1—C6—H6A119.6C30—C29—C28119.9 (3)
N1—C7—C1123.7 (3)C30—C29—N5124.0 (2)
N1—C7—H7118.1C28—C29—N5116.0 (2)
C1—C7—H7118.1C31—C30—C29119.8 (3)
C13—C8—C9118.4 (3)C31—C30—H30120.1
C13—C8—N1125.9 (3)C29—C30—H30120.1
C9—C8—N1115.7 (2)C32—C31—C30120.4 (3)
C10—C9—C8120.0 (3)C32—C31—H31119.8
C10—C9—N2125.2 (3)C30—C31—H31119.8
C8—C9—N2114.7 (2)C31—C32—C33120.5 (3)
C11—C10—C9119.6 (3)C31—C32—H32119.8
C11—C10—H10120.2C33—C32—H32119.8
C9—C10—H10120.2C32—C33—C28120.3 (3)
C12—C11—C10121.0 (3)C32—C33—H33119.9
C12—C11—H11119.5C28—C33—H33119.9
C10—C11—H11119.5N5—C34—N6115.3 (2)
C11—C12—C13119.8 (3)N5—C34—S2125.2 (2)
C11—C12—H12120.1N6—C34—S2119.5 (2)
C13—C12—H12120.1C40—C35—C36120.1 (3)
C12—C13—C8121.1 (3)C40—C35—N6119.1 (3)
C12—C13—H13119.4C36—C35—N6120.7 (3)
C8—C13—H13119.4C37—C36—C35120.1 (4)
N2—C14—N3114.2 (2)C37—C36—H36120.0
N2—C14—S1127.2 (2)C35—C36—H36120.0
N3—C14—S1118.6 (2)C38—C37—C36119.7 (5)
C16—C15—C20119.6 (3)C38—C37—H37120.1
C16—C15—N3121.7 (3)C36—C37—H37120.1
C20—C15—N3118.6 (3)C37—C38—C39120.8 (4)
C17—C16—C15119.9 (3)C37—C38—H38119.6
C17—C16—H16120.0C39—C38—H38119.6
C15—C16—H16120.0C38—C39—C40119.7 (5)
C16—C17—C18120.2 (3)C38—C39—H39120.1
C16—C17—H17119.9C40—C39—H39120.1
C18—C17—H17119.9C35—C40—C39119.5 (4)
C19—C18—C17120.0 (3)C35—C40—H40120.2
C19—C18—H18120.0C39—C40—H40120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6···S1i0.89 (1)2.77 (1)3.647 (3)168 (3)
N2—H2···N10.90 (1)2.06 (3)2.598 (3)118 (3)
N5—H5···N40.90 (1)2.16 (3)2.637 (3)113 (2)
N3—H3···S2i0.91 (1)2.42 (2)3.282 (2)160 (3)
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC20H16ClN3S
Mr365.87
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)9.410 (3), 23.079 (3), 16.807 (2)
β (°) 100.226 (2)
V3)3592.0 (13)
Z8
Radiation typeMo Kα
µ (mm1)0.34
Crystal size (mm)0.17 × 0.15 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.945, 0.951
No. of measured, independent and
observed [I > 2σ(I)] reflections
25609, 6680, 4051
Rint0.064
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.117, 1.00
No. of reflections6680
No. of parameters463
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N6—H6···S1i0.892 (10)2.769 (12)3.647 (3)168 (3)
N2—H2···N10.896 (10)2.06 (3)2.598 (3)118 (3)
N5—H5···N40.895 (10)2.16 (3)2.637 (3)113 (2)
N3—H3···S2i0.905 (10)2.418 (15)3.282 (2)160 (3)
Symmetry code: (i) x, y, z+1.
 

References

First citationBernstein, 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
First citationBruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, 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
First citationCui, 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
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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