2,4-Di-chloro-N-[eth-yl(2-hy-droxy-eth-yl)carbamo-thio-yl]benzamide.

In the title compound, C12H14Cl2N2O2S, the mol-ecule adopts a cis conformation with respect to the di-chloro-benzoyl group against the thiono group about the C-N bond. However, the di-chloro-benzene group and the thio-urea moiety are twisted by 75.41 (8)°. An intra-molecular N-H⋯O hydrogen bond occurs between the amido H atom and hydroxyl O atom. In the crystal, O-H⋯S and O-H⋯O hydrogen bonds link the molecules, forming chains along the b-axis direction.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures of thio­urea derivatives, see: Hassan et al. (2010 ▶); Nasir et al. (2011 ▶); Al-abbasi et al. (2012 ▶); Yamin et al. (2013 ▶).

Experimental

Crystal data

C12H14Cl2N2O2S

M = 321.21

Monoclinic,

a = 6.9712 (4) Å

b = 10.6989 (6) Å

c = 19.3288 (10) Å

β = 96.441 (2)°

V = 1432.52 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.60 mm−1

T = 300 K

0.50 × 0.40 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.754, T max = 0.900

30240 measured reflections

2967 independent reflections

2619 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.126

S = 1.16

2967 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker,2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813032881/rn2121sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032881/rn2121Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032881/rn2121Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H14Cl2N2O2S	F(000) = 664
Mr = 321.21	Dx = 1.489 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 18947 reflections
a = 6.9712 (4) Å	θ = 2.8–26.5°
b = 10.6989 (6) Å	µ = 0.60 mm−1
c = 19.3288 (10) Å	T = 300 K
β = 96.441 (2)°	Block, colourless
V = 1432.52 (14) Å3	0.50 × 0.40 × 0.18 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2967 independent reflections
Radiation source: fine-focus sealed tube	2619 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 83.66 pixels mm-1	θmax = 26.5°, θmin = 2.8°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.754, Tmax = 0.900	l = −24→24
30240 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0666P)2 + 0.6739P] where P = (Fo2 + 2Fc2)/3
2967 reflections	(Δ/σ)max = 0.002
176 parameters	Δρmax = 0.44 e Å−3
1 restraint	Δρmin = −0.36 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.89241 (10)	0.71322 (6)	0.93151 (4)	0.0554 (2)
Cl2	0.70111 (8)	1.08652 (6)	1.09352 (3)	0.04474 (18)
S1	0.75350 (9)	0.90835 (6)	0.64182 (3)	0.04555 (19)
O1	0.7295 (4)	0.8000 (2)	0.78711 (10)	0.0845 (9)
O2	1.0855 (3)	1.20198 (15)	0.81005 (9)	0.0448 (4)
N1	0.9083 (3)	0.97467 (17)	0.77030 (9)	0.0367 (4)
H1A	0.9742	1.0316	0.7937	0.044*
N2	1.0766 (3)	1.03352 (17)	0.68075 (9)	0.0336 (4)
C1	0.8163 (3)	0.8659 (2)	0.93868 (12)	0.0347 (5)
C2	0.7904 (3)	0.9090 (2)	1.00426 (11)	0.0341 (5)
H2B	0.8090	0.8564	1.0427	0.041*
C3	0.7364 (3)	1.0320 (2)	1.01142 (11)	0.0331 (4)
C4	0.7097 (3)	1.1128 (2)	0.95552 (12)	0.0383 (5)
H4A	0.6744	1.1956	0.9616	0.046*
C5	0.7369 (3)	1.0677 (2)	0.89040 (12)	0.0389 (5)
H5A	0.7198	1.1211	0.8523	0.047*
C6	0.7895 (3)	0.9437 (2)	0.88045 (11)	0.0348 (5)
C7	0.8036 (4)	0.8964 (2)	0.80809 (12)	0.0446 (6)
C8	0.9215 (3)	0.97372 (19)	0.69876 (11)	0.0322 (4)
C9	1.0983 (4)	1.0593 (2)	0.60741 (11)	0.0422 (5)
H9A	1.1651	1.1382	0.6043	0.051*
H9B	0.9712	1.0677	0.5817	0.051*
C10	1.2073 (4)	0.9592 (3)	0.57421 (14)	0.0611 (8)
H10A	1.2171	0.9808	0.5265	0.092*
H10B	1.1404	0.8811	0.5761	0.092*
H10C	1.3344	0.9516	0.5987	0.092*
C11	1.2412 (3)	1.0729 (2)	0.73058 (12)	0.0409 (5)
H11A	1.3576	1.0700	0.7074	0.049*
H11B	1.2566	1.0134	0.7687	0.049*
C12	1.2214 (4)	1.2026 (2)	0.76032 (14)	0.0524 (6)
H12A	1.3459	1.2306	0.7824	0.063*
H12B	1.1792	1.2604	0.7230	0.063*
H2A	1.000 (4)	1.253 (3)	0.8004 (19)	0.081 (12)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0691 (4)	0.0333 (3)	0.0679 (4)	−0.0079 (3)	0.0262 (3)	−0.0030 (3)
Cl2	0.0400 (3)	0.0580 (4)	0.0379 (3)	−0.0032 (2)	0.0114 (2)	−0.0079 (2)
S1	0.0486 (4)	0.0481 (4)	0.0379 (3)	−0.0119 (3)	−0.0042 (3)	−0.0043 (2)
O1	0.134 (2)	0.0746 (15)	0.0452 (11)	−0.0699 (15)	0.0110 (12)	−0.0104 (10)
O2	0.0520 (10)	0.0357 (9)	0.0459 (9)	0.0000 (7)	0.0017 (8)	−0.0053 (7)
N1	0.0424 (10)	0.0378 (10)	0.0308 (9)	−0.0154 (8)	0.0083 (7)	−0.0074 (7)
N2	0.0371 (9)	0.0357 (9)	0.0283 (9)	−0.0033 (7)	0.0053 (7)	−0.0009 (7)
C1	0.0263 (9)	0.0346 (11)	0.0446 (12)	−0.0094 (8)	0.0101 (8)	−0.0020 (9)
C2	0.0248 (9)	0.0414 (12)	0.0366 (11)	−0.0071 (8)	0.0059 (8)	0.0043 (9)
C3	0.0216 (9)	0.0454 (12)	0.0329 (10)	−0.0039 (8)	0.0061 (7)	−0.0021 (9)
C4	0.0310 (10)	0.0399 (12)	0.0451 (12)	0.0016 (9)	0.0090 (9)	0.0016 (9)
C5	0.0321 (11)	0.0462 (13)	0.0390 (12)	−0.0038 (9)	0.0065 (9)	0.0078 (9)
C6	0.0275 (9)	0.0429 (12)	0.0349 (11)	−0.0120 (8)	0.0072 (8)	−0.0015 (9)
C7	0.0516 (13)	0.0450 (13)	0.0378 (12)	−0.0214 (11)	0.0077 (10)	−0.0044 (10)
C8	0.0383 (11)	0.0268 (10)	0.0316 (10)	0.0000 (8)	0.0047 (8)	−0.0035 (8)
C9	0.0478 (13)	0.0489 (13)	0.0306 (11)	−0.0012 (10)	0.0070 (9)	0.0062 (9)
C10	0.0576 (16)	0.087 (2)	0.0398 (13)	0.0117 (15)	0.0123 (12)	−0.0085 (14)
C11	0.0362 (11)	0.0508 (13)	0.0362 (11)	−0.0079 (10)	0.0064 (9)	−0.0002 (10)
C12	0.0644 (16)	0.0461 (14)	0.0464 (14)	−0.0239 (12)	0.0055 (12)	−0.0024 (11)

Cl1—C1	1.728 (2)	C4—C5	1.381 (3)
Cl2—C3	1.734 (2)	C4—H4A	0.9300
S1—C8	1.668 (2)	C5—C6	1.395 (3)
O1—C7	1.203 (3)	C5—H5A	0.9300
O2—C12	1.423 (3)	C6—C7	1.501 (3)
O2—H2A	0.815 (10)	C9—C10	1.498 (4)
N1—C7	1.374 (3)	C9—H9A	0.9700
N1—C8	1.396 (3)	C9—H9B	0.9700
N1—H1A	0.8600	C10—H10A	0.9600
N2—C8	1.336 (3)	C10—H10B	0.9600
N2—C9	1.468 (3)	C10—H10C	0.9600
N2—C11	1.474 (3)	C11—C12	1.514 (4)
C1—C2	1.380 (3)	C11—H11A	0.9700
C1—C6	1.395 (3)	C11—H11B	0.9700
C2—C3	1.380 (3)	C12—H12A	0.9700
C2—H2B	0.9300	C12—H12B	0.9700
C3—C4	1.380 (3)
C12—O2—H2A	112 (3)	N2—C8—N1	113.57 (17)
C7—N1—C8	128.33 (18)	N2—C8—S1	123.90 (16)
C7—N1—H1A	115.8	N1—C8—S1	122.48 (16)
C8—N1—H1A	115.8	N2—C9—C10	113.0 (2)
C8—N2—C9	121.02 (18)	N2—C9—H9A	109.0
C8—N2—C11	124.05 (17)	C10—C9—H9A	109.0
C9—N2—C11	114.86 (17)	N2—C9—H9B	109.0
C2—C1—C6	121.5 (2)	C10—C9—H9B	109.0
C2—C1—Cl1	117.57 (17)	H9A—C9—H9B	107.8
C6—C1—Cl1	120.91 (17)	C9—C10—H10A	109.5
C1—C2—C3	118.5 (2)	C9—C10—H10B	109.5
C1—C2—H2B	120.8	H10A—C10—H10B	109.5
C3—C2—H2B	120.8	C9—C10—H10C	109.5
C2—C3—C4	122.2 (2)	H10A—C10—H10C	109.5
C2—C3—Cl2	118.74 (16)	H10B—C10—H10C	109.5
C4—C3—Cl2	119.03 (17)	N2—C11—C12	114.4 (2)
C3—C4—C5	118.3 (2)	N2—C11—H11A	108.7
C3—C4—H4A	120.8	C12—C11—H11A	108.7
C5—C4—H4A	120.8	N2—C11—H11B	108.7
C4—C5—C6	121.6 (2)	C12—C11—H11B	108.7
C4—C5—H5A	119.2	H11A—C11—H11B	107.6
C6—C5—H5A	119.2	O2—C12—C11	110.37 (19)
C1—C6—C5	118.0 (2)	O2—C12—H12A	109.6
C1—C6—C7	122.3 (2)	C11—C12—H12A	109.6
C5—C6—C7	119.6 (2)	O2—C12—H12B	109.6
O1—C7—N1	125.2 (2)	C11—C12—H12B	109.6
O1—C7—C6	122.2 (2)	H12A—C12—H12B	108.1
N1—C7—C6	112.59 (18)
C6—C1—C2—C3	0.2 (3)	C1—C6—C7—O1	44.6 (4)
Cl1—C1—C2—C3	177.72 (15)	C5—C6—C7—O1	−131.6 (3)
C1—C2—C3—C4	−0.7 (3)	C1—C6—C7—N1	−135.5 (2)
C1—C2—C3—Cl2	179.34 (15)	C5—C6—C7—N1	48.4 (3)
C2—C3—C4—C5	0.6 (3)	C9—N2—C8—N1	−170.21 (19)
Cl2—C3—C4—C5	−179.50 (16)	C11—N2—C8—N1	12.9 (3)
C3—C4—C5—C6	0.2 (3)	C9—N2—C8—S1	7.5 (3)
C2—C1—C6—C5	0.5 (3)	C11—N2—C8—S1	−169.33 (17)
Cl1—C1—C6—C5	−176.96 (15)	C7—N1—C8—N2	−160.2 (2)
C2—C1—C6—C7	−175.70 (19)	C7—N1—C8—S1	22.0 (3)
Cl1—C1—C6—C7	6.8 (3)	C8—N2—C9—C10	−92.3 (3)
C4—C5—C6—C1	−0.7 (3)	C11—N2—C9—C10	84.8 (3)
C4—C5—C6—C7	175.6 (2)	C8—N2—C11—C12	−89.9 (3)
C8—N1—C7—O1	13.0 (5)	C9—N2—C11—C12	93.1 (2)
C8—N1—C7—C6	−167.0 (2)	N2—C11—C12—O2	74.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	1.99	2.796 (3)	155
C9—H9B···S1	0.97	2.64	3.031 (3)	105
O2—H2A···S1i	0.81 (3)	2.75 (3)	3.438 (2)	143 (3)
O2—H2A···O1i	0.81 (3)	2.25 (3)	2.920 (3)	140 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.86	1.99	2.796 (3)	155
O2—H2A⋯S1i	0.81 (3)	2.75 (3)	3.438 (2)	143 (3)
O2—H2A⋯O1i	0.81 (3)	2.25 (3)	2.920 (3)	140 (3)

Symmetry code: (i) .