organic compounds
(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
The title compound, C17H13ClN2OS, crystallizes with three independent molecules (A, B and C) in the 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).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; 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.
Supporting information
10.1107/S1600536811053463/im2345sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811053463/im2345Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811053463/im2345Isup3.cml
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.
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.
Data collection: CrysAlis PRO (Agilent, 2011); cell
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).C17H13ClN2OS | F(000) = 2040 |
Mr = 328.80 | Dx = 1.404 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
a = 22.8350 (6) Å | Cell parameters from 3809 reflections |
b = 8.0587 (2) Å | θ = 3.0–29.2° |
c = 25.3653 (6) Å | µ = 0.38 mm−1 |
β = 90.900 (2)° | T = 293 K |
V = 4667.1 (2) Å3 | Block, yellow |
Z = 12 | 0.40 × 0.18 × 0.12 mm |
Agilent Xcalibur Eos diffractometer | 8224 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 5819 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 16.0874 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
ω scans | h = −27→25 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −9→9 |
Tmin = 0.909, Tmax = 1.000 | l = −20→30 |
18535 measured reflections |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-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 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C17H13ClN2OS | V = 4667.1 (2) Å3 |
Mr = 328.80 | Z = 12 |
Monoclinic, P21/n | Mo Kα radiation |
a = 22.8350 (6) Å | µ = 0.38 mm−1 |
b = 8.0587 (2) Å | T = 293 K |
c = 25.3653 (6) Å | 0.40 × 0.18 × 0.12 mm |
β = 90.900 (2)° |
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 = 1.000 | Rint = 0.020 |
18535 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.31 e Å−3 |
8224 reflections | Δρmin = −0.29 e Å−3 |
598 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1A | 0.45569 (5) | −0.04260 (15) | 0.88138 (4) | 0.1191 (4) | |
Cl1B | 0.56439 (4) | 0.16982 (13) | 0.35711 (3) | 0.0837 (3) | |
Cl1C | 0.45183 (4) | 0.73846 (13) | 0.44041 (4) | 0.0933 (3) | |
S1A | 0.19363 (3) | 0.11756 (9) | 0.64486 (3) | 0.05524 (19) | |
S1B | 0.70318 (3) | 0.14376 (10) | 0.59119 (2) | 0.0566 (2) | |
S1C | 0.60624 (3) | 0.59963 (9) | 0.65667 (2) | 0.05367 (19) | |
O1A | 0.20043 (8) | 0.0709 (3) | 0.75853 (8) | 0.0772 (6) | |
O1B | 0.81951 (9) | 0.2484 (3) | 0.48315 (8) | 0.0805 (7) | |
O1C | 0.71946 (8) | 0.6536 (3) | 0.54361 (7) | 0.0799 (7) | |
N1A | 0.28641 (9) | 0.2498 (3) | 0.60629 (8) | 0.0497 (5) | |
N1B | 0.79856 (9) | 0.1405 (3) | 0.64667 (8) | 0.0539 (6) | |
N1C | 0.70259 (9) | 0.6152 (3) | 0.71061 (7) | 0.0497 (5) | |
N2A | 0.21002 (10) | 0.2382 (3) | 0.54573 (9) | 0.0616 (6) | |
H2A | 0.2354 | 0.2638 | 0.5224 | 0.074* | |
N2B | 0.71638 (9) | 0.0969 (3) | 0.69726 (8) | 0.0562 (6) | |
H2B | 0.7404 | 0.0897 | 0.7236 | 0.067* | |
N2C | 0.62296 (9) | 0.5496 (3) | 0.76210 (8) | 0.0546 (6) | |
H2C | 0.6473 | 0.5522 | 0.7883 | 0.065* | |
C1A | 0.39626 (14) | −0.0021 (4) | 0.84015 (13) | 0.0691 (9) | |
C1B | 0.62500 (12) | 0.1768 (4) | 0.39942 (9) | 0.0528 (7) | |
C1C | 0.51593 (12) | 0.7180 (4) | 0.47725 (11) | 0.0560 (7) | |
C2A | 0.35340 (16) | 0.1049 (4) | 0.85619 (12) | 0.0743 (9) | |
H2AA | 0.3561 | 0.1564 | 0.8889 | 0.089* | |
C2B | 0.66543 (13) | 0.3021 (4) | 0.39410 (10) | 0.0574 (7) | |
H2BA | 0.6609 | 0.3811 | 0.3676 | 0.069* | |
C2C | 0.56031 (13) | 0.6191 (4) | 0.45884 (11) | 0.0619 (8) | |
H2CA | 0.5560 | 0.5629 | 0.4270 | 0.074* | |
C3A | 0.30621 (13) | 0.1348 (4) | 0.82294 (11) | 0.0632 (8) | |
H3A | 0.2766 | 0.2061 | 0.8336 | 0.076* | |
C3B | 0.71246 (12) | 0.3092 (3) | 0.42841 (10) | 0.0525 (7) | |
H3B | 0.7398 | 0.3938 | 0.4250 | 0.063* | |
C3C | 0.61108 (13) | 0.6047 (4) | 0.48832 (10) | 0.0591 (7) | |
H3C | 0.6417 | 0.5405 | 0.4757 | 0.071* | |
C4A | 0.30231 (11) | 0.0602 (3) | 0.77388 (9) | 0.0479 (6) | |
C4B | 0.71992 (11) | 0.1924 (3) | 0.46808 (9) | 0.0438 (6) | |
C4C | 0.61742 (11) | 0.6842 (3) | 0.53646 (9) | 0.0460 (6) | |
C5A | 0.34582 (12) | −0.0468 (3) | 0.75922 (11) | 0.0555 (7) | |
H5A | 0.3435 | −0.0982 | 0.7264 | 0.067* | |
C5B | 0.67921 (12) | 0.0659 (3) | 0.47177 (9) | 0.0498 (7) | |
H5B | 0.6838 | −0.0144 | 0.4978 | 0.060* | |
C5C | 0.57239 (12) | 0.7849 (3) | 0.55357 (10) | 0.0517 (7) | |
H5C | 0.5763 | 0.8414 | 0.5854 | 0.062* | |
C6A | 0.39279 (13) | −0.0794 (4) | 0.79216 (13) | 0.0648 (8) | |
H6A | 0.4218 | −0.1531 | 0.7820 | 0.078* | |
C6B | 0.63198 (12) | 0.0573 (3) | 0.43738 (10) | 0.0533 (7) | |
H6B | 0.6051 | −0.0289 | 0.4399 | 0.064* | |
C6C | 0.52187 (12) | 0.8019 (4) | 0.52375 (10) | 0.0570 (7) | |
H6C | 0.4919 | 0.8703 | 0.5353 | 0.068* | |
C7A | 0.24934 (12) | 0.0888 (3) | 0.73979 (10) | 0.0524 (7) | |
C7B | 0.77314 (12) | 0.2045 (3) | 0.50252 (10) | 0.0528 (7) | |
C7C | 0.67305 (12) | 0.6613 (3) | 0.56691 (10) | 0.0529 (7) | |
C8A | 0.25605 (11) | 0.1340 (3) | 0.68496 (9) | 0.0470 (6) | |
C8B | 0.76968 (11) | 0.1694 (3) | 0.55904 (10) | 0.0518 (7) | |
C8C | 0.67092 (11) | 0.6435 (3) | 0.62384 (9) | 0.0485 (6) | |
C9A | 0.30000 (11) | 0.2089 (3) | 0.65721 (10) | 0.0464 (6) | |
C9B | 0.81427 (11) | 0.1650 (3) | 0.59538 (10) | 0.0524 (7) | |
C9C | 0.71662 (11) | 0.6482 (3) | 0.65933 (10) | 0.0509 (7) | |
C10A | 0.23223 (12) | 0.2084 (3) | 0.59454 (10) | 0.0488 (6) | |
C10B | 0.74124 (11) | 0.1273 (3) | 0.65030 (9) | 0.0483 (6) | |
C10C | 0.64570 (11) | 0.5866 (3) | 0.71482 (9) | 0.0472 (6) | |
C11A | 0.35989 (12) | 0.2554 (3) | 0.67677 (11) | 0.0579 (7) | |
H11G | 0.3741 | 0.3477 | 0.6567 | 0.087* | |
H11H | 0.3858 | 0.1627 | 0.6728 | 0.087* | |
H11I | 0.3582 | 0.2856 | 0.7133 | 0.087* | |
C11B | 0.87818 (12) | 0.1840 (5) | 0.58394 (12) | 0.0799 (10) | |
H11D | 0.8994 | 0.2045 | 0.6162 | 0.120* | |
H11E | 0.8835 | 0.2755 | 0.5603 | 0.120* | |
H11F | 0.8924 | 0.0841 | 0.5680 | 0.120* | |
C11C | 0.77868 (11) | 0.6850 (4) | 0.64657 (11) | 0.0691 (9) | |
H11A | 0.7981 | 0.7314 | 0.6770 | 0.104* | |
H11B | 0.7799 | 0.7629 | 0.6180 | 0.104* | |
H11C | 0.7980 | 0.5843 | 0.6365 | 0.104* | |
C12A | 0.15138 (13) | 0.2336 (4) | 0.52755 (11) | 0.0563 (7) | |
C12B | 0.65685 (11) | 0.0753 (3) | 0.70944 (9) | 0.0477 (6) | |
C12C | 0.56479 (11) | 0.5072 (3) | 0.77476 (10) | 0.0493 (6) | |
C13A | 0.11009 (15) | 0.1252 (4) | 0.54626 (12) | 0.0723 (9) | |
H13A | 0.1207 | 0.0453 | 0.5711 | 0.087* | |
C13B | 0.64422 (13) | −0.0198 (3) | 0.75335 (10) | 0.0593 (7) | |
H13B | 0.6742 | −0.0717 | 0.7723 | 0.071* | |
C13C | 0.55710 (13) | 0.4119 (4) | 0.81895 (11) | 0.0634 (8) | |
H13C | 0.5894 | 0.3761 | 0.8387 | 0.076* | |
C14A | 0.05266 (16) | 0.1350 (5) | 0.52815 (14) | 0.0855 (10) | |
H14A | 0.0246 | 0.0644 | 0.5420 | 0.103* | |
C14B | 0.58682 (15) | −0.0370 (4) | 0.76867 (12) | 0.0720 (9) | |
H14B | 0.5784 | −0.0993 | 0.7985 | 0.086* | |
C14C | 0.50092 (16) | 0.3691 (4) | 0.83404 (14) | 0.0820 (10) | |
H14C | 0.4958 | 0.3042 | 0.8639 | 0.098* | |
C15A | 0.03690 (16) | 0.2461 (5) | 0.49055 (16) | 0.0896 (11) | |
H15A | −0.0017 | 0.2515 | 0.4785 | 0.107* | |
C15B | 0.54219 (14) | 0.0358 (4) | 0.74082 (13) | 0.0767 (10) | |
H15B | 0.5037 | 0.0238 | 0.7516 | 0.092* | |
C15C | 0.45340 (14) | 0.4209 (4) | 0.80572 (13) | 0.0707 (9) | |
H15C | 0.4159 | 0.3929 | 0.8164 | 0.085* | |
C16A | 0.07810 (17) | 0.3499 (5) | 0.47044 (15) | 0.0968 (12) | |
H16A | 0.0677 | 0.4250 | 0.4441 | 0.116* | |
C16B | 0.55463 (13) | 0.1259 (4) | 0.69724 (12) | 0.0739 (9) | |
H16B | 0.5242 | 0.1726 | 0.6774 | 0.089* | |
C16C | 0.46096 (13) | 0.5143 (4) | 0.76149 (12) | 0.0671 (8) | |
H16C | 0.4285 | 0.5465 | 0.7414 | 0.080* | |
C17A | 0.13499 (15) | 0.3443 (4) | 0.48897 (13) | 0.0785 (9) | |
H17A | 0.1627 | 0.4164 | 0.4752 | 0.094* | |
C17B | 0.61178 (12) | 0.1492 (4) | 0.68190 (11) | 0.0607 (7) | |
H17B | 0.6197 | 0.2152 | 0.6528 | 0.073* | |
C17C | 0.51638 (12) | 0.5616 (4) | 0.74619 (11) | 0.0579 (7) | |
H17C | 0.5211 | 0.6294 | 0.7169 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.0988 (7) | 0.1507 (10) | 0.1066 (8) | −0.0353 (7) | −0.0406 (6) | 0.0599 (7) |
Cl1B | 0.0652 (5) | 0.1387 (8) | 0.0467 (4) | 0.0200 (5) | −0.0105 (4) | −0.0027 (5) |
Cl1C | 0.0778 (6) | 0.1217 (7) | 0.0791 (6) | −0.0140 (5) | −0.0353 (5) | 0.0216 (5) |
S1A | 0.0490 (4) | 0.0690 (5) | 0.0480 (4) | −0.0036 (4) | 0.0088 (3) | 0.0057 (3) |
S1B | 0.0427 (4) | 0.0932 (5) | 0.0337 (3) | −0.0020 (4) | −0.0028 (3) | 0.0066 (3) |
S1C | 0.0447 (4) | 0.0818 (5) | 0.0344 (3) | −0.0090 (4) | −0.0047 (3) | 0.0095 (3) |
O1A | 0.0567 (13) | 0.1144 (17) | 0.0611 (13) | 0.0001 (12) | 0.0183 (10) | 0.0244 (12) |
O1B | 0.0618 (13) | 0.1272 (19) | 0.0527 (12) | −0.0209 (13) | 0.0057 (10) | 0.0213 (12) |
O1C | 0.0498 (12) | 0.146 (2) | 0.0439 (11) | 0.0114 (13) | 0.0108 (9) | 0.0207 (12) |
N1A | 0.0490 (13) | 0.0584 (13) | 0.0419 (12) | 0.0017 (11) | 0.0076 (10) | 0.0047 (10) |
N1B | 0.0414 (12) | 0.0808 (16) | 0.0392 (12) | −0.0052 (12) | −0.0025 (10) | 0.0054 (11) |
N1C | 0.0442 (13) | 0.0719 (15) | 0.0328 (11) | −0.0044 (11) | −0.0020 (9) | 0.0059 (10) |
N2A | 0.0534 (14) | 0.0877 (17) | 0.0438 (13) | 0.0038 (13) | 0.0073 (11) | 0.0087 (12) |
N2B | 0.0432 (12) | 0.0912 (17) | 0.0341 (11) | −0.0055 (12) | −0.0040 (10) | 0.0079 (11) |
N2C | 0.0438 (12) | 0.0865 (16) | 0.0331 (11) | −0.0080 (12) | −0.0051 (10) | 0.0124 (11) |
C1A | 0.067 (2) | 0.080 (2) | 0.060 (2) | −0.0218 (18) | −0.0043 (17) | 0.0289 (17) |
C1B | 0.0538 (16) | 0.0727 (18) | 0.0320 (14) | 0.0139 (15) | 0.0042 (12) | −0.0028 (13) |
C1C | 0.0577 (18) | 0.0650 (18) | 0.0452 (16) | −0.0121 (15) | −0.0080 (13) | 0.0172 (14) |
C2A | 0.086 (2) | 0.096 (2) | 0.0413 (17) | −0.029 (2) | 0.0067 (17) | −0.0022 (17) |
C2B | 0.070 (2) | 0.0656 (18) | 0.0364 (14) | 0.0218 (17) | 0.0053 (14) | 0.0132 (13) |
C2C | 0.078 (2) | 0.0686 (19) | 0.0389 (15) | −0.0053 (17) | −0.0029 (15) | 0.0020 (14) |
C3A | 0.068 (2) | 0.074 (2) | 0.0482 (17) | −0.0057 (17) | 0.0206 (15) | −0.0009 (15) |
C3B | 0.0639 (18) | 0.0537 (16) | 0.0404 (15) | 0.0042 (14) | 0.0120 (13) | 0.0065 (12) |
C3C | 0.0676 (19) | 0.0705 (18) | 0.0393 (15) | 0.0115 (16) | 0.0055 (14) | 0.0020 (14) |
C4A | 0.0550 (16) | 0.0514 (15) | 0.0378 (14) | −0.0064 (13) | 0.0138 (12) | 0.0062 (12) |
C4B | 0.0510 (15) | 0.0525 (15) | 0.0282 (12) | 0.0066 (13) | 0.0068 (11) | 0.0006 (11) |
C4C | 0.0505 (15) | 0.0559 (15) | 0.0317 (13) | −0.0014 (13) | 0.0036 (11) | 0.0092 (12) |
C5A | 0.0636 (18) | 0.0562 (16) | 0.0467 (16) | 0.0003 (15) | 0.0085 (14) | 0.0005 (13) |
C5B | 0.0600 (17) | 0.0544 (16) | 0.0351 (14) | 0.0028 (14) | 0.0034 (12) | 0.0088 (12) |
C5C | 0.0597 (17) | 0.0595 (16) | 0.0358 (14) | 0.0040 (14) | 0.0000 (13) | 0.0031 (12) |
C6A | 0.0587 (19) | 0.0608 (18) | 0.075 (2) | 0.0010 (15) | 0.0096 (17) | 0.0165 (16) |
C6B | 0.0573 (17) | 0.0607 (17) | 0.0419 (15) | −0.0040 (14) | 0.0017 (13) | −0.0014 (13) |
C6C | 0.0543 (17) | 0.0707 (18) | 0.0460 (16) | 0.0105 (15) | 0.0004 (13) | 0.0111 (14) |
C7A | 0.0536 (17) | 0.0560 (16) | 0.0479 (16) | 0.0012 (14) | 0.0132 (14) | 0.0057 (13) |
C7B | 0.0538 (17) | 0.0631 (17) | 0.0416 (15) | −0.0058 (14) | 0.0045 (13) | 0.0065 (13) |
C7C | 0.0532 (16) | 0.0668 (17) | 0.0390 (14) | 0.0019 (14) | 0.0041 (13) | 0.0102 (13) |
C8A | 0.0505 (15) | 0.0498 (15) | 0.0409 (14) | 0.0001 (13) | 0.0079 (12) | 0.0037 (12) |
C8B | 0.0444 (15) | 0.0723 (18) | 0.0388 (14) | −0.0040 (14) | 0.0020 (12) | 0.0077 (13) |
C8C | 0.0453 (15) | 0.0641 (17) | 0.0361 (13) | −0.0015 (13) | 0.0013 (11) | 0.0099 (12) |
C9A | 0.0511 (16) | 0.0455 (14) | 0.0427 (14) | 0.0017 (13) | 0.0095 (12) | 0.0005 (12) |
C9B | 0.0468 (15) | 0.0698 (18) | 0.0406 (15) | −0.0068 (14) | −0.0003 (12) | 0.0056 (13) |
C9C | 0.0449 (15) | 0.0636 (17) | 0.0443 (15) | −0.0001 (14) | 0.0010 (12) | 0.0081 (13) |
C10A | 0.0517 (17) | 0.0517 (15) | 0.0432 (15) | 0.0065 (13) | 0.0073 (12) | 0.0021 (12) |
C10B | 0.0455 (15) | 0.0653 (17) | 0.0338 (13) | −0.0035 (14) | −0.0030 (11) | 0.0038 (12) |
C10C | 0.0445 (15) | 0.0604 (16) | 0.0364 (14) | −0.0013 (13) | −0.0049 (11) | 0.0059 (12) |
C11A | 0.0573 (18) | 0.0618 (17) | 0.0546 (17) | −0.0069 (15) | 0.0053 (14) | 0.0079 (14) |
C11B | 0.0435 (17) | 0.137 (3) | 0.0593 (19) | −0.0101 (19) | 0.0020 (14) | 0.0202 (19) |
C11C | 0.0416 (16) | 0.109 (2) | 0.0566 (18) | −0.0021 (16) | −0.0001 (13) | 0.0177 (17) |
C12A | 0.0599 (18) | 0.0638 (18) | 0.0453 (16) | 0.0028 (16) | 0.0004 (14) | −0.0076 (14) |
C12B | 0.0464 (15) | 0.0611 (16) | 0.0354 (14) | −0.0049 (13) | −0.0008 (12) | −0.0052 (12) |
C12C | 0.0479 (16) | 0.0598 (16) | 0.0401 (14) | −0.0063 (13) | 0.0023 (12) | 0.0003 (13) |
C13A | 0.083 (2) | 0.072 (2) | 0.0616 (19) | −0.0138 (19) | −0.0119 (17) | −0.0002 (16) |
C13B | 0.0643 (19) | 0.0659 (18) | 0.0476 (16) | −0.0031 (15) | −0.0001 (14) | 0.0043 (14) |
C13C | 0.0631 (19) | 0.075 (2) | 0.0522 (17) | −0.0060 (16) | 0.0051 (14) | 0.0137 (15) |
C14A | 0.079 (2) | 0.101 (3) | 0.076 (2) | −0.031 (2) | −0.014 (2) | −0.013 (2) |
C14B | 0.080 (2) | 0.078 (2) | 0.0579 (19) | −0.0186 (19) | 0.0162 (18) | 0.0050 (16) |
C14C | 0.086 (3) | 0.085 (2) | 0.076 (2) | −0.013 (2) | 0.028 (2) | 0.0233 (19) |
C15A | 0.073 (2) | 0.102 (3) | 0.093 (3) | −0.009 (2) | −0.027 (2) | −0.013 (2) |
C15B | 0.0543 (19) | 0.103 (3) | 0.074 (2) | −0.0167 (19) | 0.0163 (17) | −0.008 (2) |
C15C | 0.0528 (19) | 0.076 (2) | 0.084 (2) | −0.0141 (17) | 0.0217 (17) | 0.0027 (19) |
C16A | 0.089 (3) | 0.101 (3) | 0.099 (3) | −0.006 (2) | −0.034 (2) | 0.024 (2) |
C16B | 0.0487 (18) | 0.108 (3) | 0.065 (2) | 0.0086 (18) | 0.0009 (15) | −0.0023 (19) |
C16C | 0.0509 (18) | 0.077 (2) | 0.073 (2) | −0.0091 (16) | 0.0009 (15) | −0.0079 (17) |
C17A | 0.069 (2) | 0.091 (2) | 0.075 (2) | −0.0071 (19) | −0.0120 (18) | 0.0187 (19) |
C17B | 0.0511 (17) | 0.084 (2) | 0.0470 (16) | 0.0031 (16) | 0.0039 (13) | 0.0096 (15) |
C17C | 0.0475 (16) | 0.0748 (19) | 0.0512 (17) | −0.0091 (15) | −0.0003 (13) | 0.0057 (14) |
Cl1A—C1A | 1.731 (3) | C5C—C6C | 1.376 (3) |
Cl1B—C1B | 1.739 (3) | C6A—H6A | 0.9300 |
Cl1C—C1C | 1.732 (3) | C6B—H6B | 0.9300 |
S1A—C8A | 1.743 (3) | C6C—H6C | 0.9300 |
S1A—C10A | 1.725 (3) | C7A—C8A | 1.448 (3) |
S1B—C8B | 1.747 (3) | C7B—C8B | 1.465 (3) |
S1B—C10B | 1.726 (2) | C7C—C8C | 1.453 (3) |
S1C—C8C | 1.743 (2) | C8A—C9A | 1.375 (3) |
S1C—C10C | 1.720 (2) | C8B—C9B | 1.363 (3) |
O1A—C7A | 1.229 (3) | C8C—C9C | 1.368 (3) |
O1B—C7B | 1.226 (3) | C9A—C11A | 1.495 (3) |
O1C—C7C | 1.223 (3) | C9B—C11B | 1.500 (3) |
N1A—C9A | 1.364 (3) | C9C—C11C | 1.489 (3) |
N1A—C10A | 1.311 (3) | C11A—H11G | 0.9600 |
N1B—C9B | 1.369 (3) | C11A—H11H | 0.9600 |
N1B—C10B | 1.318 (3) | C11A—H11I | 0.9600 |
N1C—C9C | 1.370 (3) | C11B—H11D | 0.9600 |
N1C—C10C | 1.326 (3) | C11B—H11E | 0.9600 |
N2A—H2A | 0.8600 | C11B—H11F | 0.9600 |
N2A—C10A | 1.352 (3) | C11C—H11A | 0.9600 |
N2A—C12A | 1.410 (3) | C11C—H11B | 0.9600 |
N2B—H2B | 0.8600 | C11C—H11C | 0.9600 |
N2B—C10B | 1.350 (3) | C12A—C13A | 1.375 (4) |
N2B—C12B | 1.410 (3) | C12A—C17A | 1.372 (4) |
N2C—H2C | 0.8600 | C12B—C13B | 1.386 (3) |
N2C—C10C | 1.348 (3) | C12B—C17B | 1.371 (3) |
N2C—C12C | 1.414 (3) | C12C—C13C | 1.372 (4) |
C1A—C2A | 1.371 (4) | C12C—C17C | 1.383 (4) |
C1A—C6A | 1.369 (4) | C13A—H13A | 0.9300 |
C1B—C2B | 1.377 (4) | C13A—C14A | 1.385 (4) |
C1B—C6B | 1.369 (4) | C13B—H13B | 0.9300 |
C1C—C2C | 1.377 (4) | C13B—C14B | 1.380 (4) |
C1C—C6C | 1.365 (4) | C13C—H13C | 0.9300 |
C2A—H2AA | 0.9300 | C13C—C14C | 1.388 (4) |
C2A—C3A | 1.379 (4) | C14A—H14A | 0.9300 |
C2B—H2BA | 0.9300 | C14A—C15A | 1.352 (5) |
C2B—C3B | 1.373 (4) | C14B—H14B | 0.9300 |
C2C—H2CA | 0.9300 | C14B—C15B | 1.364 (4) |
C2C—C3C | 1.375 (4) | C14C—H14C | 0.9300 |
C3A—H3A | 0.9300 | C14C—C15C | 1.358 (4) |
C3A—C4A | 1.384 (4) | C15A—H15A | 0.9300 |
C3B—H3B | 0.9300 | C15A—C16A | 1.364 (5) |
C3B—C4B | 1.386 (3) | C15B—H15B | 0.9300 |
C3C—H3C | 0.9300 | C15B—C16B | 1.356 (4) |
C3C—C4C | 1.385 (3) | C15C—H15C | 0.9300 |
C4A—C5A | 1.371 (3) | C15C—C16C | 1.364 (4) |
C4A—C7A | 1.494 (4) | C16A—H16A | 0.9300 |
C4B—C5B | 1.384 (3) | C16A—C17A | 1.375 (4) |
C4B—C7B | 1.489 (3) | C16B—H16B | 0.9300 |
C4C—C5C | 1.385 (3) | C16B—C17B | 1.381 (4) |
C4C—C7C | 1.488 (3) | C16C—H16C | 0.9300 |
C5A—H5A | 0.9300 | C16C—C17C | 1.383 (4) |
C5A—C6A | 1.375 (4) | C17A—H17A | 0.9300 |
C5B—H5B | 0.9300 | C17B—H17B | 0.9300 |
C5B—C6B | 1.378 (3) | C17C—H17C | 0.9300 |
C5C—H5C | 0.9300 | ||
C10A—S1A—C8A | 88.68 (12) | C8A—C9A—C11A | 127.7 (2) |
C10B—S1B—C8B | 89.14 (12) | N1B—C9B—C11B | 118.0 (2) |
C10C—S1C—C8C | 89.17 (12) | C8B—C9B—N1B | 116.2 (2) |
C10A—N1A—C9A | 110.7 (2) | C8B—C9B—C11B | 125.8 (2) |
C10B—N1B—C9B | 110.7 (2) | N1C—C9C—C11C | 118.8 (2) |
C10C—N1C—C9C | 110.7 (2) | C8C—C9C—N1C | 115.6 (2) |
C10A—N2A—H2A | 115.3 | C8C—C9C—C11C | 125.6 (2) |
C10A—N2A—C12A | 129.5 (2) | N1A—C10A—S1A | 115.5 (2) |
C12A—N2A—H2A | 115.3 | N1A—C10A—N2A | 120.1 (2) |
C10B—N2B—H2B | 115.2 | N2A—C10A—S1A | 124.3 (2) |
C10B—N2B—C12B | 129.5 (2) | N1B—C10B—S1B | 114.85 (18) |
C12B—N2B—H2B | 115.2 | N1B—C10B—N2B | 120.5 (2) |
C10C—N2C—H2C | 115.4 | N2B—C10B—S1B | 124.6 (2) |
C10C—N2C—C12C | 129.2 (2) | N1C—C10C—S1C | 114.92 (18) |
C12C—N2C—H2C | 115.4 | N1C—C10C—N2C | 120.1 (2) |
C2A—C1A—Cl1A | 119.7 (3) | N2C—C10C—S1C | 124.9 (2) |
C6A—C1A—Cl1A | 119.0 (3) | C9A—C11A—H11G | 109.5 |
C6A—C1A—C2A | 121.2 (3) | C9A—C11A—H11H | 109.5 |
C2B—C1B—Cl1B | 119.4 (2) | C9A—C11A—H11I | 109.5 |
C6B—C1B—Cl1B | 119.6 (2) | H11G—C11A—H11H | 109.5 |
C6B—C1B—C2B | 121.0 (3) | H11G—C11A—H11I | 109.5 |
C2C—C1C—Cl1C | 119.5 (2) | H11H—C11A—H11I | 109.5 |
C6C—C1C—Cl1C | 119.4 (2) | C9B—C11B—H11D | 109.5 |
C6C—C1C—C2C | 121.1 (3) | C9B—C11B—H11E | 109.5 |
C1A—C2A—H2AA | 120.6 | C9B—C11B—H11F | 109.5 |
C1A—C2A—C3A | 118.9 (3) | H11D—C11B—H11E | 109.5 |
C3A—C2A—H2AA | 120.6 | H11D—C11B—H11F | 109.5 |
C1B—C2B—H2BA | 120.4 | H11E—C11B—H11F | 109.5 |
C3B—C2B—C1B | 119.2 (2) | C9C—C11C—H11A | 109.5 |
C3B—C2B—H2BA | 120.4 | C9C—C11C—H11B | 109.5 |
C1C—C2C—H2CA | 120.5 | C9C—C11C—H11C | 109.5 |
C3C—C2C—C1C | 118.9 (3) | H11A—C11C—H11B | 109.5 |
C3C—C2C—H2CA | 120.5 | H11A—C11C—H11C | 109.5 |
C2A—C3A—H3A | 119.6 | H11B—C11C—H11C | 109.5 |
C2A—C3A—C4A | 120.8 (3) | C13A—C12A—N2A | 123.8 (3) |
C4A—C3A—H3A | 119.6 | C17A—C12A—N2A | 117.6 (3) |
C2B—C3B—H3B | 119.4 | C17A—C12A—C13A | 118.6 (3) |
C2B—C3B—C4B | 121.2 (3) | C13B—C12B—N2B | 117.3 (2) |
C4B—C3B—H3B | 119.4 | C17B—C12B—N2B | 123.6 (2) |
C2C—C3C—H3C | 119.5 | C17B—C12B—C13B | 119.1 (2) |
C2C—C3C—C4C | 121.1 (3) | C13C—C12C—N2C | 117.0 (2) |
C4C—C3C—H3C | 119.5 | C13C—C12C—C17C | 119.6 (3) |
C3A—C4A—C7A | 119.6 (2) | C17C—C12C—N2C | 123.4 (2) |
C5A—C4A—C3A | 118.7 (3) | C12A—C13A—H13A | 120.0 |
C5A—C4A—C7A | 121.6 (2) | C12A—C13A—C14A | 120.0 (3) |
C3B—C4B—C7B | 118.1 (2) | C14A—C13A—H13A | 120.0 |
C5B—C4B—C3B | 118.3 (2) | C12B—C13B—H13B | 120.3 |
C5B—C4B—C7B | 123.5 (2) | C14B—C13B—C12B | 119.5 (3) |
C3C—C4C—C5C | 118.7 (2) | C14B—C13B—H13B | 120.3 |
C3C—C4C—C7C | 118.5 (2) | C12C—C13C—H13C | 120.2 |
C5C—C4C—C7C | 122.8 (2) | C12C—C13C—C14C | 119.7 (3) |
C4A—C5A—H5A | 119.4 | C14C—C13C—H13C | 120.2 |
C4A—C5A—C6A | 121.1 (3) | C13A—C14A—H14A | 119.6 |
C6A—C5A—H5A | 119.4 | C15A—C14A—C13A | 120.8 (3) |
C4B—C5B—H5B | 119.5 | C15A—C14A—H14A | 119.6 |
C6B—C5B—C4B | 120.9 (2) | C13B—C14B—H14B | 119.5 |
C6B—C5B—H5B | 119.5 | C15B—C14B—C13B | 121.1 (3) |
C4C—C5C—H5C | 119.8 | C15B—C14B—H14B | 119.5 |
C6C—C5C—C4C | 120.4 (2) | C13C—C14C—H14C | 119.6 |
C6C—C5C—H5C | 119.8 | C15C—C14C—C13C | 120.8 (3) |
C1A—C6A—C5A | 119.2 (3) | C15C—C14C—H14C | 119.6 |
C1A—C6A—H6A | 120.4 | C14A—C15A—H15A | 120.3 |
C5A—C6A—H6A | 120.4 | C14A—C15A—C16A | 119.5 (3) |
C1B—C6B—C5B | 119.4 (3) | C16A—C15A—H15A | 120.3 |
C1B—C6B—H6B | 120.3 | C14B—C15B—H15B | 120.4 |
C5B—C6B—H6B | 120.3 | C16B—C15B—C14B | 119.2 (3) |
C1C—C6C—C5C | 119.8 (3) | C16B—C15B—H15B | 120.4 |
C1C—C6C—H6C | 120.1 | C14C—C15C—H15C | 120.2 |
C5C—C6C—H6C | 120.1 | C14C—C15C—C16C | 119.6 (3) |
O1A—C7A—C4A | 119.4 (2) | C16C—C15C—H15C | 120.2 |
O1A—C7A—C8A | 120.8 (3) | C15A—C16A—H16A | 119.8 |
C8A—C7A—C4A | 119.9 (2) | C15A—C16A—C17A | 120.3 (3) |
O1B—C7B—C4B | 119.1 (2) | C17A—C16A—H16A | 119.8 |
O1B—C7B—C8B | 120.5 (3) | C15B—C16B—H16B | 119.5 |
C8B—C7B—C4B | 120.4 (2) | C15B—C16B—C17B | 120.9 (3) |
O1C—C7C—C4C | 119.6 (2) | C17B—C16B—H16B | 119.5 |
O1C—C7C—C8C | 121.2 (2) | C15C—C16C—H16C | 119.6 |
C8C—C7C—C4C | 119.1 (2) | C15C—C16C—C17C | 120.7 (3) |
C7A—C8A—S1A | 116.33 (19) | C17C—C16C—H16C | 119.6 |
C9A—C8A—S1A | 109.35 (18) | C12A—C17A—C16A | 120.7 (3) |
C9A—C8A—C7A | 133.7 (3) | C12A—C17A—H17A | 119.6 |
C7B—C8B—S1B | 122.7 (2) | C16A—C17A—H17A | 119.6 |
C9B—C8B—S1B | 109.08 (18) | C12B—C17B—C16B | 120.2 (3) |
C9B—C8B—C7B | 128.0 (2) | C12B—C17B—H17B | 119.9 |
C7C—C8C—S1C | 122.5 (2) | C16B—C17B—H17B | 119.9 |
C9C—C8C—S1C | 109.55 (18) | C12C—C17C—H17C | 120.2 |
C9C—C8C—C7C | 127.9 (2) | C16C—C17C—C12C | 119.5 (3) |
N1A—C9A—C8A | 115.7 (2) | C16C—C17C—H17C | 120.2 |
N1A—C9A—C11A | 116.6 (2) |
D—H···A | D—H | H···A | D···A | 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+3/2, y−1/2, −z+3/2; (iii) −x+3/2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C17H13ClN2OS |
Mr | 328.80 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 22.8350 (6), 8.0587 (2), 25.3653 (6) |
β (°) | 90.900 (2) |
V (Å3) | 4667.1 (2) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.40 × 0.18 × 0.12 |
Data collection | |
Diffractometer | Agilent Xcalibur Eos diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.909, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18535, 8224, 5819 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.110, 1.02 |
No. of reflections | 8224 |
No. of parameters | 598 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O1Ci | 0.86 | 2.09 | 2.933 (3) | 167.1 |
N2B—H2B···N1Cii | 0.86 | 2.11 | 2.962 (3) | 170.4 |
N2C—H2C···N1Biii | 0.86 | 2.17 | 2.995 (3) | 162.0 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y−1/2, −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
Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Dolomanov, 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 Google Scholar
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Moisés, R., Adriana, A., Raymundo, C., Aydee, F., Rosa, M. & Andrés, P. (2000). J. Org. Chem. 65, 7244–7247. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
(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.