(2Z)-3-(2,4-Di-chloro-phen-yl)-3-hy-droxy-N-phenyl-prop-2-ene-thio-amide.

In the title mol-ecule, C15H11Cl2NOS, the dihedral angle between the phenyl and benzene rings is 72.24 (1)°. In the crystal, pairs of N-H⋯S hydrogen bonds form dimers with twofold rotational symmetry. The dimers are connected by weak C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (001). An intra-molecular O-H⋯S hydrogen bond is also observed.

Related literature

For the biological activity and applications of thio­amides, see: Zahid et al. (2009 ▶); Jagodzinski (2003 ▶); Lebana et al. (2008 ▶). For the synthesis of thio­amides, see: Bauer & Kuhlein (1985 ▶); Cava & Levinson (1985 ▶). For the synthesis of the title compound, see: Rudrof et al. (1979 ▶). For related structures, see: Xu et al. (2005 ▶); Cowley et al. (2002 ▶); Jiang (2009 ▶); Patil et al. (2011 ▶); Deshmukh et al. (2009 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H11Cl2NOS

M = 324.21

Orthorhombic,

a = 28.9562 (6) Å

b = 13.2610 (3) Å

c = 7.5284 (2) Å

V = 2890.82 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.59 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.835, T max = 1.000

63107 measured reflections

2836 independent reflections

2275 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.091

S = 1.11

2836 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: 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: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017339/lh5625sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017339/lh5625Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017339/lh5625Isup3.cml

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

C15H11Cl2NOS	F(000) = 1328
Mr = 324.21	Dx = 1.490 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 24816 reflections
a = 28.9562 (6) Å	θ = 3.4–29.1°
b = 13.2610 (3) Å	µ = 0.59 mm−1
c = 7.5284 (2) Å	T = 293 K
V = 2890.82 (12) Å3	Block, orange
Z = 8	0.3 × 0.2 × 0.1 mm

Agilent Xcalibur Sapphire3 diffractometer	2836 independent reflections
Radiation source: fine-focus sealed tube	2275 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scan	h = −35→35
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −16→16
Tmin = 0.835, Tmax = 1.000	l = −9→9
63107 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0293P)2 + 2.0935P] where P = (Fo2 + 2Fc2)/3
2836 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) 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
S1	0.31822 (2)	0.16889 (5)	0.20313 (10)	0.04414 (18)
O1	0.41937 (6)	0.17165 (12)	0.2188 (3)	0.0476 (5)
N1	0.29969 (6)	0.36160 (14)	0.2171 (3)	0.0391 (5)
H1	0.2719	0.3391	0.2114	0.047*
Cl1	0.44813 (2)	0.49703 (5)	0.15039 (11)	0.0581 (2)
Cl2	0.61091 (2)	0.40683 (7)	0.43216 (13)	0.0718 (3)
C1	0.33303 (8)	0.29196 (17)	0.2249 (3)	0.0338 (5)
C1'	0.46507 (7)	0.31015 (16)	0.2953 (3)	0.0320 (5)
C2	0.37934 (7)	0.32640 (17)	0.2576 (3)	0.0333 (5)
H2	0.3828	0.3945	0.2840	0.040*
C2'	0.48099 (8)	0.40787 (17)	0.2622 (3)	0.0360 (5)
C3	0.41830 (7)	0.27056 (16)	0.2540 (3)	0.0315 (5)
C3'	0.52538 (8)	0.43770 (19)	0.3058 (3)	0.0430 (6)
H3'	0.5351	0.5033	0.2834	0.052*
C4	0.30453 (7)	0.46842 (17)	0.2172 (3)	0.0343 (5)
C4'	0.55494 (8)	0.3693 (2)	0.3827 (3)	0.0440 (6)
C5	0.28010 (8)	0.5236 (2)	0.3398 (4)	0.0463 (6)
H5	0.2619	0.4912	0.4241	0.056*
C5'	0.54086 (8)	0.2721 (2)	0.4168 (4)	0.0478 (7)
H5'	0.5610	0.2261	0.4685	0.057*
C6	0.28268 (10)	0.6273 (2)	0.3371 (4)	0.0565 (8)
H6	0.2661	0.6647	0.4200	0.068*
C6'	0.49660 (8)	0.2442 (2)	0.3733 (3)	0.0404 (6)
H6'	0.4873	0.1784	0.3969	0.048*
C7	0.30932 (10)	0.6760 (2)	0.2137 (4)	0.0534 (7)
H7	0.3111	0.7460	0.2134	0.064*
C8	0.33346 (9)	0.6208 (2)	0.0902 (4)	0.0476 (7)
H8	0.3515	0.6537	0.0062	0.057*
C9	0.33111 (8)	0.51666 (18)	0.0900 (3)	0.0401 (6)
H9	0.3472	0.4795	0.0055	0.048*
H11	0.3902 (11)	0.152 (2)	0.210 (4)	0.070 (10)*

	U11	U22	U33	U12	U13	U23
S1	0.0340 (3)	0.0307 (3)	0.0677 (4)	−0.0066 (3)	0.0007 (3)	0.0007 (3)
O1	0.0327 (10)	0.0286 (9)	0.0816 (13)	0.0008 (7)	0.0009 (9)	−0.0031 (9)
N1	0.0216 (10)	0.0322 (10)	0.0636 (14)	−0.0034 (8)	−0.0027 (9)	0.0025 (10)
Cl1	0.0339 (3)	0.0381 (3)	0.1022 (6)	−0.0011 (3)	−0.0061 (4)	0.0241 (4)
Cl2	0.0333 (4)	0.0834 (6)	0.0989 (6)	−0.0046 (4)	−0.0186 (4)	−0.0110 (5)
C1	0.0319 (13)	0.0313 (12)	0.0382 (13)	−0.0035 (10)	0.0017 (10)	0.0014 (10)
C1'	0.0279 (11)	0.0327 (12)	0.0354 (12)	0.0031 (9)	0.0028 (9)	0.0003 (10)
C2	0.0292 (12)	0.0258 (11)	0.0451 (13)	−0.0016 (9)	0.0008 (10)	0.0000 (10)
C2'	0.0298 (12)	0.0331 (12)	0.0452 (13)	0.0025 (10)	0.0006 (10)	0.0015 (11)
C3	0.0303 (12)	0.0268 (12)	0.0375 (12)	0.0001 (9)	0.0028 (10)	0.0023 (10)
C3'	0.0322 (13)	0.0378 (13)	0.0591 (16)	−0.0023 (11)	−0.0001 (12)	−0.0034 (12)
C4	0.0236 (11)	0.0310 (12)	0.0484 (14)	0.0020 (9)	−0.0073 (10)	0.0016 (11)
C4'	0.0270 (13)	0.0569 (16)	0.0480 (15)	−0.0003 (11)	−0.0039 (11)	−0.0075 (13)
C5	0.0357 (14)	0.0479 (15)	0.0552 (16)	0.0073 (11)	0.0058 (12)	0.0036 (13)
C5'	0.0363 (14)	0.0518 (17)	0.0552 (16)	0.0091 (12)	−0.0079 (12)	0.0076 (13)
C6	0.0555 (18)	0.0457 (16)	0.069 (2)	0.0163 (14)	−0.0018 (15)	−0.0087 (15)
C6'	0.0343 (13)	0.0391 (13)	0.0477 (14)	0.0028 (11)	0.0003 (11)	0.0094 (12)
C7	0.0519 (17)	0.0324 (14)	0.076 (2)	0.0054 (12)	−0.0157 (15)	0.0011 (14)
C8	0.0381 (14)	0.0434 (15)	0.0613 (17)	−0.0052 (11)	−0.0074 (13)	0.0148 (13)
C9	0.0301 (13)	0.0420 (14)	0.0481 (14)	0.0000 (10)	−0.0002 (11)	0.0021 (12)

S1—C1	1.695 (2)	C3'—H3'	0.9300
O1—C3	1.339 (3)	C4—C5	1.374 (3)
O1—H11	0.89 (3)	C4—C9	1.385 (3)
N1—C1	1.337 (3)	C4'—C5'	1.376 (4)
N1—C4	1.423 (3)	C5—C6	1.377 (4)
N1—H1	0.8600	C5—H5	0.9300
Cl1—C2'	1.735 (2)	C5'—C6'	1.374 (3)
Cl2—C4'	1.736 (2)	C5'—H5'	0.9300
C1—C2	1.438 (3)	C6—C7	1.369 (4)
C1'—C6'	1.394 (3)	C6—H6	0.9300
C1'—C2'	1.398 (3)	C6'—H6'	0.9300
C1'—C3	1.485 (3)	C7—C8	1.374 (4)
C2—C3	1.350 (3)	C7—H7	0.9300
C2—H2	0.9300	C8—C9	1.382 (3)
C2'—C3'	1.384 (3)	C8—H8	0.9300
C3'—C4'	1.375 (3)	C9—H9	0.9300
C3—O1—H11	106 (2)	C3'—C4'—C5'	120.8 (2)
C1—N1—C4	128.05 (19)	C3'—C4'—Cl2	118.8 (2)
C1—N1—H1	116.0	C5'—C4'—Cl2	120.3 (2)
C4—N1—H1	116.0	C4—C5—C6	119.6 (3)
N1—C1—C2	117.5 (2)	C4—C5—H5	120.2
N1—C1—S1	118.57 (17)	C6—C5—H5	120.2
C2—C1—S1	123.93 (17)	C6'—C5'—C4'	119.0 (2)
C6'—C1'—C2'	116.2 (2)	C6'—C5'—H5'	120.5
C6'—C1'—C3	117.6 (2)	C4'—C5'—H5'	120.5
C2'—C1'—C3	126.2 (2)	C7—C6—C5	120.7 (3)
C3—C2—C1	127.0 (2)	C7—C6—H6	119.6
C3—C2—H2	116.5	C5—C6—H6	119.6
C1—C2—H2	116.5	C5'—C6'—C1'	122.8 (2)
C3'—C2'—C1'	121.9 (2)	C5'—C6'—H6'	118.6
C3'—C2'—Cl1	115.43 (18)	C1'—C6'—H6'	118.6
C1'—C2'—Cl1	122.49 (18)	C6—C7—C8	119.7 (3)
O1—C3—C2	124.1 (2)	C6—C7—H7	120.2
O1—C3—C1'	111.51 (18)	C8—C7—H7	120.2
C2—C3—C1'	124.3 (2)	C7—C8—C9	120.5 (3)
C4'—C3'—C2'	119.3 (2)	C7—C8—H8	119.7
C4'—C3'—H3'	120.3	C9—C8—H8	119.7
C2'—C3'—H3'	120.3	C8—C9—C4	119.2 (2)
C5—C4—C9	120.3 (2)	C8—C9—H9	120.4
C5—C4—N1	118.7 (2)	C4—C9—H9	120.4
C9—C4—N1	120.9 (2)
C4—N1—C1—C2	7.8 (4)	C1—N1—C4—C9	56.9 (4)
C4—N1—C1—S1	−174.3 (2)	C2'—C3'—C4'—C5'	−0.1 (4)
N1—C1—C2—C3	−173.3 (2)	C2'—C3'—C4'—Cl2	178.55 (19)
S1—C1—C2—C3	8.9 (4)	C9—C4—C5—C6	−0.9 (4)
C6'—C1'—C2'—C3'	−0.6 (3)	N1—C4—C5—C6	−177.1 (2)
C3—C1'—C2'—C3'	180.0 (2)	C3'—C4'—C5'—C6'	−0.2 (4)
C6'—C1'—C2'—Cl1	174.85 (18)	Cl2—C4'—C5'—C6'	−178.9 (2)
C3—C1'—C2'—Cl1	−4.6 (3)	C4—C5—C6—C7	0.0 (4)
C1—C2—C3—O1	−0.2 (4)	C4'—C5'—C6'—C1'	0.1 (4)
C1—C2—C3—C1'	−177.8 (2)	C2'—C1'—C6'—C5'	0.3 (4)
C6'—C1'—C3—O1	−29.6 (3)	C3—C1'—C6'—C5'	179.7 (2)
C2'—C1'—C3—O1	149.8 (2)	C5—C6—C7—C8	0.5 (4)
C6'—C1'—C3—C2	148.2 (2)	C6—C7—C8—C9	−0.1 (4)
C2'—C1'—C3—C2	−32.4 (4)	C7—C8—C9—C4	−0.8 (4)
C1'—C2'—C3'—C4'	0.5 (4)	C5—C4—C9—C8	1.3 (4)
Cl1—C2'—C3'—C4'	−175.2 (2)	N1—C4—C9—C8	177.4 (2)
C1—N1—C4—C5	−126.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.86	2.61	3.4397 (18)	162
C3′—H3′···O1ii	0.93	2.59	3.496 (3)	164
O1—H11···S1	0.89 (3)	2.10 (3)	2.9315 (18)	157 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.86	2.61	3.4397 (18)	162
C3′—H3′⋯O1ii	0.93	2.59	3.496 (3)	164
O1—H11⋯S1	0.89 (3)	2.10 (3)	2.9315 (18)	157 (2)

Symmetry codes: (i) ; (ii) .