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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(2-Anilino-4-methyl­thia­zol-5-yl)(4-chloro­phen­yl)methanone

aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China
*Correspondence e-mail: xieym@scu.edu.cn

(Received 28 November 2011; accepted 12 December 2011; online 17 December 2011)

The title compound, C17H13ClN2OS, crystallizes with three independent mol­ecules (A, B and C) in the asymmetric unit which differ slightly in their conformations. In mol­ecule A, the thiazole ring makes dihedral angles of 27.44 (14) and 66.05 (6)° with the phenyl and chloro­benzene rings. In mol­ecule B, the respective angles are 29.09 (10) and 47.63 (9)°, while values of 25.67 (11) and 51.01 (7)° are observed in mol­ecule C. In the crystal, N—H⋯N and N—H⋯O hydrogen bonds generate a three-dimensional network structure.

Related literature

For the biological activity and synthesis of phen­yl(thia­zol-5-yl)methanone derivatives, see: Moisés et al. (2000[Moisés, R., Adriana, A., Raymundo, C., Aydee, F., Rosa, M. & Andrés, P. (2000). J. Org. Chem. 65, 7244-7247.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13ClN2OS

  • Mr = 328.80

  • Monoclinic, P 21 /n

  • a = 22.8350 (6) Å

  • b = 8.0587 (2) Å

  • c = 25.3653 (6) Å

  • β = 90.900 (2)°

  • V = 4667.1 (2) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 0.38 mm−1

  • T = 293 K

  • 0.40 × 0.18 × 0.12 mm

Data collection
  • Agilent Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.909, Tmax = 1.000

  • 18535 measured reflections

  • 8224 independent reflections

  • 5819 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.110

  • S = 1.02

  • 8224 reflections

  • 598 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2A—H2A⋯O1Ci 0.86 2.09 2.933 (3) 167
N2B—H2B⋯N1Cii 0.86 2.11 2.962 (3) 170
N2C—H2C⋯N1Biii 0.86 2.17 2.995 (3) 162
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: OLEX2.

Supporting information


Comment top

(4-chlorophenyl)(4-methyl-2-(phenylamino)thiazol-5-yl)methanone derivatives are of great importance owing to their wide biological properties. The title compound is one of the key products in our synthetic investigations of antitumor drugs. We report here its crystal structure.

The title compound, C17H13ClN2OS, crystallizes with three independent molecules (A, B and C) per asymmetric unit. The independent molecules differ slightly in their conformations. In molecule A, the triazole ring makes dihedral angles of 27.44 (14)° and 66.05 (6)° with the phenyl and chlorobenzene rings. In molecule B the respective angles are 29.09 (10)° and 47.63 (9)°, while values of 25.67 (11)° and 51.01 (7)° are observed in molecule C. The molecules show intermolecular N2B—H2B···N1C, N2C—H2C···N1B and N2A—H2A···O1C hydrogen bonds. These bonds together with non-classical hydrogen bonds produce the oberved three dimensional network structure.

Related literature top

For the biological activity and synthesis of phenyl(thiazol-5-yl)methanone derivatives, see: Moisés et al. (2000).

Experimental top

A suspension of acetimidamide hydrochloride (378.0 mg, 4.0 mmol) in THF (10.0 ml) was added to aqueous sodium hydroxide (1.6 ml, 2.5 N) and phenyl isothiocyanate (546.1 mg, 4.0 mmol) at 0°. The reaction mixture was stirred for 1–2 h at this temperature. It was then diluted with ethyl acetate (4.0 ml), the organic phase was washed with brine. Evaporation of the solvent in vacuo gave the N-(phenylcarbamothioyl)acetimidamide as solid.

N-(phenylcarbamothioyl)acetimidamide (386.5 mg, 2.0 mmol) was added to a solution of 2-bromo-1-(4-chlorophenyl)ethanone (524.2 mg, 2.2 mmol) in acetone containing triethylamine (0.28 ml, 2.0 mmol) at room temperature. After being stirred for 5–8 h, ethyl acetate was added, the organic phase was washed twice with brineand was afterwards evaporated in vacuo. The residue was recrystallized from ethanol to give the title compound as a light yellow solid (364.7 mg, 55.6% yield). Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of dichloromethane.

Refinement top

All H atoms were positioned geometrically and refined as rinding (C—H = 0.93–0.96 Å, N–H =0.86 Å) and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound. Hydrogen bonds are shown as blue dotted lines.
(2-Anilino-4-methylthiazol-5-yl)(4-chlorophenyl)methanone top
Crystal data top
C17H13ClN2OSF(000) = 2040
Mr = 328.80Dx = 1.404 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.7107 Å
a = 22.8350 (6) ÅCell parameters from 3809 reflections
b = 8.0587 (2) Åθ = 3.0–29.2°
c = 25.3653 (6) ŵ = 0.38 mm1
β = 90.900 (2)°T = 293 K
V = 4667.1 (2) Å3Block, yellow
Z = 120.40 × 0.18 × 0.12 mm
Data collection top
Agilent Xcalibur Eos
diffractometer
8224 independent reflections
Radiation source: Enhance (Mo) X-ray Source5819 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 16.0874 pixels mm-1θmax = 25.0°, θmin = 3.0°
ω scansh = 2725
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
k = 99
Tmin = 0.909, Tmax = 1.000l = 2030
18535 measured reflections
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0402P)2 + 1.7472P]
where P = (Fo2 + 2Fc2)/3
8224 reflections(Δ/σ)max = 0.001
598 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C17H13ClN2OSV = 4667.1 (2) Å3
Mr = 328.80Z = 12
Monoclinic, P21/nMo Kα radiation
a = 22.8350 (6) ŵ = 0.38 mm1
b = 8.0587 (2) ÅT = 293 K
c = 25.3653 (6) Å0.40 × 0.18 × 0.12 mm
β = 90.900 (2)°
Data collection top
Agilent Xcalibur Eos
diffractometer
8224 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
5819 reflections with I > 2σ(I)
Tmin = 0.909, Tmax = 1.000Rint = 0.020
18535 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.02Δρmax = 0.31 e Å3
8224 reflectionsΔρmin = 0.29 e Å3
598 parameters
Special details top

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1A0.45569 (5)0.04260 (15)0.88138 (4)0.1191 (4)
Cl1B0.56439 (4)0.16982 (13)0.35711 (3)0.0837 (3)
Cl1C0.45183 (4)0.73846 (13)0.44041 (4)0.0933 (3)
S1A0.19363 (3)0.11756 (9)0.64486 (3)0.05524 (19)
S1B0.70318 (3)0.14376 (10)0.59119 (2)0.0566 (2)
S1C0.60624 (3)0.59963 (9)0.65667 (2)0.05367 (19)
O1A0.20043 (8)0.0709 (3)0.75853 (8)0.0772 (6)
O1B0.81951 (9)0.2484 (3)0.48315 (8)0.0805 (7)
O1C0.71946 (8)0.6536 (3)0.54361 (7)0.0799 (7)
N1A0.28641 (9)0.2498 (3)0.60629 (8)0.0497 (5)
N1B0.79856 (9)0.1405 (3)0.64667 (8)0.0539 (6)
N1C0.70259 (9)0.6152 (3)0.71061 (7)0.0497 (5)
N2A0.21002 (10)0.2382 (3)0.54573 (9)0.0616 (6)
H2A0.23540.26380.52240.074*
N2B0.71638 (9)0.0969 (3)0.69726 (8)0.0562 (6)
H2B0.74040.08970.72360.067*
N2C0.62296 (9)0.5496 (3)0.76210 (8)0.0546 (6)
H2C0.64730.55220.78830.065*
C1A0.39626 (14)0.0021 (4)0.84015 (13)0.0691 (9)
C1B0.62500 (12)0.1768 (4)0.39942 (9)0.0528 (7)
C1C0.51593 (12)0.7180 (4)0.47725 (11)0.0560 (7)
C2A0.35340 (16)0.1049 (4)0.85619 (12)0.0743 (9)
H2AA0.35610.15640.88890.089*
C2B0.66543 (13)0.3021 (4)0.39410 (10)0.0574 (7)
H2BA0.66090.38110.36760.069*
C2C0.56031 (13)0.6191 (4)0.45884 (11)0.0619 (8)
H2CA0.55600.56290.42700.074*
C3A0.30621 (13)0.1348 (4)0.82294 (11)0.0632 (8)
H3A0.27660.20610.83360.076*
C3B0.71246 (12)0.3092 (3)0.42841 (10)0.0525 (7)
H3B0.73980.39380.42500.063*
C3C0.61108 (13)0.6047 (4)0.48832 (10)0.0591 (7)
H3C0.64170.54050.47570.071*
C4A0.30231 (11)0.0602 (3)0.77388 (9)0.0479 (6)
C4B0.71992 (11)0.1924 (3)0.46808 (9)0.0438 (6)
C4C0.61742 (11)0.6842 (3)0.53646 (9)0.0460 (6)
C5A0.34582 (12)0.0468 (3)0.75922 (11)0.0555 (7)
H5A0.34350.09820.72640.067*
C5B0.67921 (12)0.0659 (3)0.47177 (9)0.0498 (7)
H5B0.68380.01440.49780.060*
C5C0.57239 (12)0.7849 (3)0.55357 (10)0.0517 (7)
H5C0.57630.84140.58540.062*
C6A0.39279 (13)0.0794 (4)0.79216 (13)0.0648 (8)
H6A0.42180.15310.78200.078*
C6B0.63198 (12)0.0573 (3)0.43738 (10)0.0533 (7)
H6B0.60510.02890.43990.064*
C6C0.52187 (12)0.8019 (4)0.52375 (10)0.0570 (7)
H6C0.49190.87030.53530.068*
C7A0.24934 (12)0.0888 (3)0.73979 (10)0.0524 (7)
C7B0.77314 (12)0.2045 (3)0.50252 (10)0.0528 (7)
C7C0.67305 (12)0.6613 (3)0.56691 (10)0.0529 (7)
C8A0.25605 (11)0.1340 (3)0.68496 (9)0.0470 (6)
C8B0.76968 (11)0.1694 (3)0.55904 (10)0.0518 (7)
C8C0.67092 (11)0.6435 (3)0.62384 (9)0.0485 (6)
C9A0.30000 (11)0.2089 (3)0.65721 (10)0.0464 (6)
C9B0.81427 (11)0.1650 (3)0.59538 (10)0.0524 (7)
C9C0.71662 (11)0.6482 (3)0.65933 (10)0.0509 (7)
C10A0.23223 (12)0.2084 (3)0.59454 (10)0.0488 (6)
C10B0.74124 (11)0.1273 (3)0.65030 (9)0.0483 (6)
C10C0.64570 (11)0.5866 (3)0.71482 (9)0.0472 (6)
C11A0.35989 (12)0.2554 (3)0.67677 (11)0.0579 (7)
H11G0.37410.34770.65670.087*
H11H0.38580.16270.67280.087*
H11I0.35820.28560.71330.087*
C11B0.87818 (12)0.1840 (5)0.58394 (12)0.0799 (10)
H11D0.89940.20450.61620.120*
H11E0.88350.27550.56030.120*
H11F0.89240.08410.56800.120*
C11C0.77868 (11)0.6850 (4)0.64657 (11)0.0691 (9)
H11A0.79810.73140.67700.104*
H11B0.77990.76290.61800.104*
H11C0.79800.58430.63650.104*
C12A0.15138 (13)0.2336 (4)0.52755 (11)0.0563 (7)
C12B0.65685 (11)0.0753 (3)0.70944 (9)0.0477 (6)
C12C0.56479 (11)0.5072 (3)0.77476 (10)0.0493 (6)
C13A0.11009 (15)0.1252 (4)0.54626 (12)0.0723 (9)
H13A0.12070.04530.57110.087*
C13B0.64422 (13)0.0198 (3)0.75335 (10)0.0593 (7)
H13B0.67420.07170.77230.071*
C13C0.55710 (13)0.4119 (4)0.81895 (11)0.0634 (8)
H13C0.58940.37610.83870.076*
C14A0.05266 (16)0.1350 (5)0.52815 (14)0.0855 (10)
H14A0.02460.06440.54200.103*
C14B0.58682 (15)0.0370 (4)0.76867 (12)0.0720 (9)
H14B0.57840.09930.79850.086*
C14C0.50092 (16)0.3691 (4)0.83404 (14)0.0820 (10)
H14C0.49580.30420.86390.098*
C15A0.03690 (16)0.2461 (5)0.49055 (16)0.0896 (11)
H15A0.00170.25150.47850.107*
C15B0.54219 (14)0.0358 (4)0.74082 (13)0.0767 (10)
H15B0.50370.02380.75160.092*
C15C0.45340 (14)0.4209 (4)0.80572 (13)0.0707 (9)
H15C0.41590.39290.81640.085*
C16A0.07810 (17)0.3499 (5)0.47044 (15)0.0968 (12)
H16A0.06770.42500.44410.116*
C16B0.55463 (13)0.1259 (4)0.69724 (12)0.0739 (9)
H16B0.52420.17260.67740.089*
C16C0.46096 (13)0.5143 (4)0.76149 (12)0.0671 (8)
H16C0.42850.54650.74140.080*
C17A0.13499 (15)0.3443 (4)0.48897 (13)0.0785 (9)
H17A0.16270.41640.47520.094*
C17B0.61178 (12)0.1492 (4)0.68190 (11)0.0607 (7)
H17B0.61970.21520.65280.073*
C17C0.51638 (12)0.5616 (4)0.74619 (11)0.0579 (7)
H17C0.52110.62940.71690.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0988 (7)0.1507 (10)0.1066 (8)0.0353 (7)0.0406 (6)0.0599 (7)
Cl1B0.0652 (5)0.1387 (8)0.0467 (4)0.0200 (5)0.0105 (4)0.0027 (5)
Cl1C0.0778 (6)0.1217 (7)0.0791 (6)0.0140 (5)0.0353 (5)0.0216 (5)
S1A0.0490 (4)0.0690 (5)0.0480 (4)0.0036 (4)0.0088 (3)0.0057 (3)
S1B0.0427 (4)0.0932 (5)0.0337 (3)0.0020 (4)0.0028 (3)0.0066 (3)
S1C0.0447 (4)0.0818 (5)0.0344 (3)0.0090 (4)0.0047 (3)0.0095 (3)
O1A0.0567 (13)0.1144 (17)0.0611 (13)0.0001 (12)0.0183 (10)0.0244 (12)
O1B0.0618 (13)0.1272 (19)0.0527 (12)0.0209 (13)0.0057 (10)0.0213 (12)
O1C0.0498 (12)0.146 (2)0.0439 (11)0.0114 (13)0.0108 (9)0.0207 (12)
N1A0.0490 (13)0.0584 (13)0.0419 (12)0.0017 (11)0.0076 (10)0.0047 (10)
N1B0.0414 (12)0.0808 (16)0.0392 (12)0.0052 (12)0.0025 (10)0.0054 (11)
N1C0.0442 (13)0.0719 (15)0.0328 (11)0.0044 (11)0.0020 (9)0.0059 (10)
N2A0.0534 (14)0.0877 (17)0.0438 (13)0.0038 (13)0.0073 (11)0.0087 (12)
N2B0.0432 (12)0.0912 (17)0.0341 (11)0.0055 (12)0.0040 (10)0.0079 (11)
N2C0.0438 (12)0.0865 (16)0.0331 (11)0.0080 (12)0.0051 (10)0.0124 (11)
C1A0.067 (2)0.080 (2)0.060 (2)0.0218 (18)0.0043 (17)0.0289 (17)
C1B0.0538 (16)0.0727 (18)0.0320 (14)0.0139 (15)0.0042 (12)0.0028 (13)
C1C0.0577 (18)0.0650 (18)0.0452 (16)0.0121 (15)0.0080 (13)0.0172 (14)
C2A0.086 (2)0.096 (2)0.0413 (17)0.029 (2)0.0067 (17)0.0022 (17)
C2B0.070 (2)0.0656 (18)0.0364 (14)0.0218 (17)0.0053 (14)0.0132 (13)
C2C0.078 (2)0.0686 (19)0.0389 (15)0.0053 (17)0.0029 (15)0.0020 (14)
C3A0.068 (2)0.074 (2)0.0482 (17)0.0057 (17)0.0206 (15)0.0009 (15)
C3B0.0639 (18)0.0537 (16)0.0404 (15)0.0042 (14)0.0120 (13)0.0065 (12)
C3C0.0676 (19)0.0705 (18)0.0393 (15)0.0115 (16)0.0055 (14)0.0020 (14)
C4A0.0550 (16)0.0514 (15)0.0378 (14)0.0064 (13)0.0138 (12)0.0062 (12)
C4B0.0510 (15)0.0525 (15)0.0282 (12)0.0066 (13)0.0068 (11)0.0006 (11)
C4C0.0505 (15)0.0559 (15)0.0317 (13)0.0014 (13)0.0036 (11)0.0092 (12)
C5A0.0636 (18)0.0562 (16)0.0467 (16)0.0003 (15)0.0085 (14)0.0005 (13)
C5B0.0600 (17)0.0544 (16)0.0351 (14)0.0028 (14)0.0034 (12)0.0088 (12)
C5C0.0597 (17)0.0595 (16)0.0358 (14)0.0040 (14)0.0000 (13)0.0031 (12)
C6A0.0587 (19)0.0608 (18)0.075 (2)0.0010 (15)0.0096 (17)0.0165 (16)
C6B0.0573 (17)0.0607 (17)0.0419 (15)0.0040 (14)0.0017 (13)0.0014 (13)
C6C0.0543 (17)0.0707 (18)0.0460 (16)0.0105 (15)0.0004 (13)0.0111 (14)
C7A0.0536 (17)0.0560 (16)0.0479 (16)0.0012 (14)0.0132 (14)0.0057 (13)
C7B0.0538 (17)0.0631 (17)0.0416 (15)0.0058 (14)0.0045 (13)0.0065 (13)
C7C0.0532 (16)0.0668 (17)0.0390 (14)0.0019 (14)0.0041 (13)0.0102 (13)
C8A0.0505 (15)0.0498 (15)0.0409 (14)0.0001 (13)0.0079 (12)0.0037 (12)
C8B0.0444 (15)0.0723 (18)0.0388 (14)0.0040 (14)0.0020 (12)0.0077 (13)
C8C0.0453 (15)0.0641 (17)0.0361 (13)0.0015 (13)0.0013 (11)0.0099 (12)
C9A0.0511 (16)0.0455 (14)0.0427 (14)0.0017 (13)0.0095 (12)0.0005 (12)
C9B0.0468 (15)0.0698 (18)0.0406 (15)0.0068 (14)0.0003 (12)0.0056 (13)
C9C0.0449 (15)0.0636 (17)0.0443 (15)0.0001 (14)0.0010 (12)0.0081 (13)
C10A0.0517 (17)0.0517 (15)0.0432 (15)0.0065 (13)0.0073 (12)0.0021 (12)
C10B0.0455 (15)0.0653 (17)0.0338 (13)0.0035 (14)0.0030 (11)0.0038 (12)
C10C0.0445 (15)0.0604 (16)0.0364 (14)0.0013 (13)0.0049 (11)0.0059 (12)
C11A0.0573 (18)0.0618 (17)0.0546 (17)0.0069 (15)0.0053 (14)0.0079 (14)
C11B0.0435 (17)0.137 (3)0.0593 (19)0.0101 (19)0.0020 (14)0.0202 (19)
C11C0.0416 (16)0.109 (2)0.0566 (18)0.0021 (16)0.0001 (13)0.0177 (17)
C12A0.0599 (18)0.0638 (18)0.0453 (16)0.0028 (16)0.0004 (14)0.0076 (14)
C12B0.0464 (15)0.0611 (16)0.0354 (14)0.0049 (13)0.0008 (12)0.0052 (12)
C12C0.0479 (16)0.0598 (16)0.0401 (14)0.0063 (13)0.0023 (12)0.0003 (13)
C13A0.083 (2)0.072 (2)0.0616 (19)0.0138 (19)0.0119 (17)0.0002 (16)
C13B0.0643 (19)0.0659 (18)0.0476 (16)0.0031 (15)0.0001 (14)0.0043 (14)
C13C0.0631 (19)0.075 (2)0.0522 (17)0.0060 (16)0.0051 (14)0.0137 (15)
C14A0.079 (2)0.101 (3)0.076 (2)0.031 (2)0.014 (2)0.013 (2)
C14B0.080 (2)0.078 (2)0.0579 (19)0.0186 (19)0.0162 (18)0.0050 (16)
C14C0.086 (3)0.085 (2)0.076 (2)0.013 (2)0.028 (2)0.0233 (19)
C15A0.073 (2)0.102 (3)0.093 (3)0.009 (2)0.027 (2)0.013 (2)
C15B0.0543 (19)0.103 (3)0.074 (2)0.0167 (19)0.0163 (17)0.008 (2)
C15C0.0528 (19)0.076 (2)0.084 (2)0.0141 (17)0.0217 (17)0.0027 (19)
C16A0.089 (3)0.101 (3)0.099 (3)0.006 (2)0.034 (2)0.024 (2)
C16B0.0487 (18)0.108 (3)0.065 (2)0.0086 (18)0.0009 (15)0.0023 (19)
C16C0.0509 (18)0.077 (2)0.073 (2)0.0091 (16)0.0009 (15)0.0079 (17)
C17A0.069 (2)0.091 (2)0.075 (2)0.0071 (19)0.0120 (18)0.0187 (19)
C17B0.0511 (17)0.084 (2)0.0470 (16)0.0031 (16)0.0039 (13)0.0096 (15)
C17C0.0475 (16)0.0748 (19)0.0512 (17)0.0091 (15)0.0003 (13)0.0057 (14)
Geometric parameters (Å, º) top
Cl1A—C1A1.731 (3)C5C—C6C1.376 (3)
Cl1B—C1B1.739 (3)C6A—H6A0.9300
Cl1C—C1C1.732 (3)C6B—H6B0.9300
S1A—C8A1.743 (3)C6C—H6C0.9300
S1A—C10A1.725 (3)C7A—C8A1.448 (3)
S1B—C8B1.747 (3)C7B—C8B1.465 (3)
S1B—C10B1.726 (2)C7C—C8C1.453 (3)
S1C—C8C1.743 (2)C8A—C9A1.375 (3)
S1C—C10C1.720 (2)C8B—C9B1.363 (3)
O1A—C7A1.229 (3)C8C—C9C1.368 (3)
O1B—C7B1.226 (3)C9A—C11A1.495 (3)
O1C—C7C1.223 (3)C9B—C11B1.500 (3)
N1A—C9A1.364 (3)C9C—C11C1.489 (3)
N1A—C10A1.311 (3)C11A—H11G0.9600
N1B—C9B1.369 (3)C11A—H11H0.9600
N1B—C10B1.318 (3)C11A—H11I0.9600
N1C—C9C1.370 (3)C11B—H11D0.9600
N1C—C10C1.326 (3)C11B—H11E0.9600
N2A—H2A0.8600C11B—H11F0.9600
N2A—C10A1.352 (3)C11C—H11A0.9600
N2A—C12A1.410 (3)C11C—H11B0.9600
N2B—H2B0.8600C11C—H11C0.9600
N2B—C10B1.350 (3)C12A—C13A1.375 (4)
N2B—C12B1.410 (3)C12A—C17A1.372 (4)
N2C—H2C0.8600C12B—C13B1.386 (3)
N2C—C10C1.348 (3)C12B—C17B1.371 (3)
N2C—C12C1.414 (3)C12C—C13C1.372 (4)
C1A—C2A1.371 (4)C12C—C17C1.383 (4)
C1A—C6A1.369 (4)C13A—H13A0.9300
C1B—C2B1.377 (4)C13A—C14A1.385 (4)
C1B—C6B1.369 (4)C13B—H13B0.9300
C1C—C2C1.377 (4)C13B—C14B1.380 (4)
C1C—C6C1.365 (4)C13C—H13C0.9300
C2A—H2AA0.9300C13C—C14C1.388 (4)
C2A—C3A1.379 (4)C14A—H14A0.9300
C2B—H2BA0.9300C14A—C15A1.352 (5)
C2B—C3B1.373 (4)C14B—H14B0.9300
C2C—H2CA0.9300C14B—C15B1.364 (4)
C2C—C3C1.375 (4)C14C—H14C0.9300
C3A—H3A0.9300C14C—C15C1.358 (4)
C3A—C4A1.384 (4)C15A—H15A0.9300
C3B—H3B0.9300C15A—C16A1.364 (5)
C3B—C4B1.386 (3)C15B—H15B0.9300
C3C—H3C0.9300C15B—C16B1.356 (4)
C3C—C4C1.385 (3)C15C—H15C0.9300
C4A—C5A1.371 (3)C15C—C16C1.364 (4)
C4A—C7A1.494 (4)C16A—H16A0.9300
C4B—C5B1.384 (3)C16A—C17A1.375 (4)
C4B—C7B1.489 (3)C16B—H16B0.9300
C4C—C5C1.385 (3)C16B—C17B1.381 (4)
C4C—C7C1.488 (3)C16C—H16C0.9300
C5A—H5A0.9300C16C—C17C1.383 (4)
C5A—C6A1.375 (4)C17A—H17A0.9300
C5B—H5B0.9300C17B—H17B0.9300
C5B—C6B1.378 (3)C17C—H17C0.9300
C5C—H5C0.9300
C10A—S1A—C8A88.68 (12)C8A—C9A—C11A127.7 (2)
C10B—S1B—C8B89.14 (12)N1B—C9B—C11B118.0 (2)
C10C—S1C—C8C89.17 (12)C8B—C9B—N1B116.2 (2)
C10A—N1A—C9A110.7 (2)C8B—C9B—C11B125.8 (2)
C10B—N1B—C9B110.7 (2)N1C—C9C—C11C118.8 (2)
C10C—N1C—C9C110.7 (2)C8C—C9C—N1C115.6 (2)
C10A—N2A—H2A115.3C8C—C9C—C11C125.6 (2)
C10A—N2A—C12A129.5 (2)N1A—C10A—S1A115.5 (2)
C12A—N2A—H2A115.3N1A—C10A—N2A120.1 (2)
C10B—N2B—H2B115.2N2A—C10A—S1A124.3 (2)
C10B—N2B—C12B129.5 (2)N1B—C10B—S1B114.85 (18)
C12B—N2B—H2B115.2N1B—C10B—N2B120.5 (2)
C10C—N2C—H2C115.4N2B—C10B—S1B124.6 (2)
C10C—N2C—C12C129.2 (2)N1C—C10C—S1C114.92 (18)
C12C—N2C—H2C115.4N1C—C10C—N2C120.1 (2)
C2A—C1A—Cl1A119.7 (3)N2C—C10C—S1C124.9 (2)
C6A—C1A—Cl1A119.0 (3)C9A—C11A—H11G109.5
C6A—C1A—C2A121.2 (3)C9A—C11A—H11H109.5
C2B—C1B—Cl1B119.4 (2)C9A—C11A—H11I109.5
C6B—C1B—Cl1B119.6 (2)H11G—C11A—H11H109.5
C6B—C1B—C2B121.0 (3)H11G—C11A—H11I109.5
C2C—C1C—Cl1C119.5 (2)H11H—C11A—H11I109.5
C6C—C1C—Cl1C119.4 (2)C9B—C11B—H11D109.5
C6C—C1C—C2C121.1 (3)C9B—C11B—H11E109.5
C1A—C2A—H2AA120.6C9B—C11B—H11F109.5
C1A—C2A—C3A118.9 (3)H11D—C11B—H11E109.5
C3A—C2A—H2AA120.6H11D—C11B—H11F109.5
C1B—C2B—H2BA120.4H11E—C11B—H11F109.5
C3B—C2B—C1B119.2 (2)C9C—C11C—H11A109.5
C3B—C2B—H2BA120.4C9C—C11C—H11B109.5
C1C—C2C—H2CA120.5C9C—C11C—H11C109.5
C3C—C2C—C1C118.9 (3)H11A—C11C—H11B109.5
C3C—C2C—H2CA120.5H11A—C11C—H11C109.5
C2A—C3A—H3A119.6H11B—C11C—H11C109.5
C2A—C3A—C4A120.8 (3)C13A—C12A—N2A123.8 (3)
C4A—C3A—H3A119.6C17A—C12A—N2A117.6 (3)
C2B—C3B—H3B119.4C17A—C12A—C13A118.6 (3)
C2B—C3B—C4B121.2 (3)C13B—C12B—N2B117.3 (2)
C4B—C3B—H3B119.4C17B—C12B—N2B123.6 (2)
C2C—C3C—H3C119.5C17B—C12B—C13B119.1 (2)
C2C—C3C—C4C121.1 (3)C13C—C12C—N2C117.0 (2)
C4C—C3C—H3C119.5C13C—C12C—C17C119.6 (3)
C3A—C4A—C7A119.6 (2)C17C—C12C—N2C123.4 (2)
C5A—C4A—C3A118.7 (3)C12A—C13A—H13A120.0
C5A—C4A—C7A121.6 (2)C12A—C13A—C14A120.0 (3)
C3B—C4B—C7B118.1 (2)C14A—C13A—H13A120.0
C5B—C4B—C3B118.3 (2)C12B—C13B—H13B120.3
C5B—C4B—C7B123.5 (2)C14B—C13B—C12B119.5 (3)
C3C—C4C—C5C118.7 (2)C14B—C13B—H13B120.3
C3C—C4C—C7C118.5 (2)C12C—C13C—H13C120.2
C5C—C4C—C7C122.8 (2)C12C—C13C—C14C119.7 (3)
C4A—C5A—H5A119.4C14C—C13C—H13C120.2
C4A—C5A—C6A121.1 (3)C13A—C14A—H14A119.6
C6A—C5A—H5A119.4C15A—C14A—C13A120.8 (3)
C4B—C5B—H5B119.5C15A—C14A—H14A119.6
C6B—C5B—C4B120.9 (2)C13B—C14B—H14B119.5
C6B—C5B—H5B119.5C15B—C14B—C13B121.1 (3)
C4C—C5C—H5C119.8C15B—C14B—H14B119.5
C6C—C5C—C4C120.4 (2)C13C—C14C—H14C119.6
C6C—C5C—H5C119.8C15C—C14C—C13C120.8 (3)
C1A—C6A—C5A119.2 (3)C15C—C14C—H14C119.6
C1A—C6A—H6A120.4C14A—C15A—H15A120.3
C5A—C6A—H6A120.4C14A—C15A—C16A119.5 (3)
C1B—C6B—C5B119.4 (3)C16A—C15A—H15A120.3
C1B—C6B—H6B120.3C14B—C15B—H15B120.4
C5B—C6B—H6B120.3C16B—C15B—C14B119.2 (3)
C1C—C6C—C5C119.8 (3)C16B—C15B—H15B120.4
C1C—C6C—H6C120.1C14C—C15C—H15C120.2
C5C—C6C—H6C120.1C14C—C15C—C16C119.6 (3)
O1A—C7A—C4A119.4 (2)C16C—C15C—H15C120.2
O1A—C7A—C8A120.8 (3)C15A—C16A—H16A119.8
C8A—C7A—C4A119.9 (2)C15A—C16A—C17A120.3 (3)
O1B—C7B—C4B119.1 (2)C17A—C16A—H16A119.8
O1B—C7B—C8B120.5 (3)C15B—C16B—H16B119.5
C8B—C7B—C4B120.4 (2)C15B—C16B—C17B120.9 (3)
O1C—C7C—C4C119.6 (2)C17B—C16B—H16B119.5
O1C—C7C—C8C121.2 (2)C15C—C16C—H16C119.6
C8C—C7C—C4C119.1 (2)C15C—C16C—C17C120.7 (3)
C7A—C8A—S1A116.33 (19)C17C—C16C—H16C119.6
C9A—C8A—S1A109.35 (18)C12A—C17A—C16A120.7 (3)
C9A—C8A—C7A133.7 (3)C12A—C17A—H17A119.6
C7B—C8B—S1B122.7 (2)C16A—C17A—H17A119.6
C9B—C8B—S1B109.08 (18)C12B—C17B—C16B120.2 (3)
C9B—C8B—C7B128.0 (2)C12B—C17B—H17B119.9
C7C—C8C—S1C122.5 (2)C16B—C17B—H17B119.9
C9C—C8C—S1C109.55 (18)C12C—C17C—H17C120.2
C9C—C8C—C7C127.9 (2)C16C—C17C—C12C119.5 (3)
N1A—C9A—C8A115.7 (2)C16C—C17C—H17C120.2
N1A—C9A—C11A116.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O1Ci0.862.092.933 (3)167
N2B—H2B···N1Cii0.862.112.962 (3)170
N2C—H2C···N1Biii0.862.172.995 (3)162
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+3/2, y1/2, z+3/2; (iii) x+3/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC17H13ClN2OS
Mr328.80
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)22.8350 (6), 8.0587 (2), 25.3653 (6)
β (°) 90.900 (2)
V3)4667.1 (2)
Z12
Radiation typeMo Kα
µ (mm1)0.38
Crystal size (mm)0.40 × 0.18 × 0.12
Data collection
DiffractometerAgilent Xcalibur Eos
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.909, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
18535, 8224, 5819
Rint0.020
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.110, 1.02
No. of reflections8224
No. of parameters598
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.29

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O1Ci0.862.092.933 (3)167.1
N2B—H2B···N1Cii0.862.112.962 (3)170.4
N2C—H2C···N1Biii0.862.172.995 (3)162.0
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+3/2, y1/2, z+3/2; (iii) x+3/2, y+1/2, z+3/2.
 

Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

First citationAgilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals
First citationMoisés, R., Adriana, A., Raymundo, C., Aydee, F., Rosa, M. & Andrés, P. (2000). J. Org. Chem. 65, 7244–7247.  Web of Science PubMed
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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