1-(4-Chloro-butano-yl)-3-(2-chloro-phen-yl)thio-urea.

The asymmetric unit of the title compound, C(11)H(12)Cl(2)N(2)OS, contains two crystallographically independent mol-ecules with different conformations: the benzene ring and the thio-urea fragment form dihedral angles of 74.32 (11) and 89.39 (11)°. One amino group in each mol-ecule is involved in intra-molecular N-H⋯O and inter-molecular N-H⋯O hydrogen bonding: the latter links pairs of independent mol-ecules into dimers. In the crystal, weak N-H⋯S inter-actions link these dimers into chains propagating along the c axis.

Related literature

For a related structure, see: Yusof et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H12Cl2N2OS

M = 291.19

Monoclinic,

a = 14.396 (3) Å

b = 10.941 (2) Å

c = 18.093 (4) Å

β = 109.399 (4)°

V = 2688.0 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.62 mm−1

T = 298 K

0.42 × 0.41 × 0.39 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.780, T max = 0.793

14457 measured reflections

4727 independent reflections

3802 reflections with I > 2/s(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.03

4727 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201759X/cv5287sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201759X/cv5287Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201759X/cv5287Isup3.cml

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

C11H12Cl2N2OS	F(000) = 1200
Mr = 291.19	Dx = 1.439 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6026 reflections
a = 14.396 (3) Å	θ = 1.5–25.0°
b = 10.941 (2) Å	µ = 0.62 mm−1
c = 18.093 (4) Å	T = 298 K
β = 109.399 (4)°	Block, yellow
V = 2688.0 (9) Å3	0.42 × 0.41 × 0.39 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	4727 independent reflections
Radiation source: fine-focus sealed tube	3802 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 83.66 pixels mm-1	θmax = 25.0°, θmin = 1.5°
ω scan	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −13→12
Tmin = 0.780, Tmax = 0.793	l = −16→21
14457 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0514P)2 + 1.5167P] where P = (Fo2 + 2Fc2)/3
4727 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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	−0.02869 (4)	−0.00674 (6)	0.33632 (3)	0.04643 (17)
S2	0.23770 (4)	0.49698 (6)	0.02320 (4)	0.04616 (17)
Cl1	−0.08277 (6)	−0.17066 (6)	0.15579 (5)	0.0684 (2)
Cl2	0.52142 (7)	0.18550 (11)	0.47501 (6)	0.1086 (4)
Cl3	0.38361 (6)	0.18324 (8)	0.09743 (5)	0.0738 (2)
Cl4	−0.23405 (6)	0.18796 (9)	−0.20368 (5)	0.0792 (3)
O1	0.20202 (12)	0.12434 (18)	0.23359 (10)	0.0555 (5)
O2	0.05946 (12)	0.18451 (16)	0.07274 (10)	0.0543 (5)
N1	0.01342 (13)	0.07137 (17)	0.21195 (10)	0.0385 (4)
H1A	0.0562	0.0916	0.1904	0.046*
N2	0.14546 (13)	0.04033 (17)	0.32535 (11)	0.0400 (4)
H2A	0.1648	0.0114	0.3722	0.048*
N3	0.21846 (13)	0.32495 (18)	0.11973 (11)	0.0430 (5)
H3A	0.1852	0.2670	0.1311	0.052*
N4	0.08539 (13)	0.35124 (17)	0.00731 (11)	0.0382 (4)
H4A	0.0585	0.3957	−0.0334	0.046*
C1	−0.14018 (18)	−0.0300 (2)	0.13660 (14)	0.0450 (6)
C2	−0.2387 (2)	−0.0240 (3)	0.09106 (16)	0.0620 (8)
H2	−0.2740	−0.0952	0.0724	0.074*
C3	−0.2839 (2)	0.0878 (3)	0.07364 (18)	0.0734 (9)
H3	−0.3500	0.0921	0.0431	0.088*
C4	−0.2326 (2)	0.1928 (3)	0.10078 (19)	0.0683 (8)
H4	−0.2636	0.2682	0.0878	0.082*
C5	−0.13441 (19)	0.1870 (2)	0.14771 (16)	0.0540 (6)
H5	−0.0997	0.2584	0.1669	0.065*
C6	−0.08857 (16)	0.0750 (2)	0.16572 (13)	0.0394 (5)
C7	0.04504 (15)	0.03795 (19)	0.28697 (13)	0.0358 (5)
C8	0.21855 (16)	0.0824 (2)	0.29900 (14)	0.0437 (5)
C9	0.31985 (18)	0.0696 (3)	0.35824 (16)	0.0608 (7)
H9A	0.3219	0.1128	0.4056	0.073*
H9B	0.3322	−0.0161	0.3715	0.073*
C10	0.39933 (19)	0.1170 (3)	0.33112 (17)	0.0644 (8)
H10A	0.3885	0.2036	0.3200	0.077*
H10B	0.3955	0.0764	0.2825	0.077*
C11	0.5010 (2)	0.0994 (4)	0.38907 (18)	0.0743 (9)
H11A	0.5491	0.1226	0.3647	0.089*
H11B	0.5107	0.0135	0.4027	0.089*
C12	0.39626 (18)	0.2933 (2)	0.16893 (14)	0.0487 (6)
C13	0.48814 (19)	0.3193 (3)	0.22162 (17)	0.0610 (7)
H13	0.5437	0.2795	0.2183	0.073*
C14	0.4967 (2)	0.4046 (3)	0.27902 (18)	0.0690 (8)
H14	0.5584	0.4223	0.3149	0.083*
C15	0.4150 (2)	0.4644 (3)	0.28422 (18)	0.0700 (8)
H15	0.4217	0.5219	0.3235	0.084*
C16	0.32314 (19)	0.4390 (3)	0.23107 (16)	0.0562 (7)
H16	0.2679	0.4798	0.2343	0.067*
C17	0.31345 (16)	0.3533 (2)	0.17331 (13)	0.0435 (6)
C18	0.17954 (15)	0.3847 (2)	0.05298 (12)	0.0355 (5)
C19	0.02925 (16)	0.2559 (2)	0.01862 (13)	0.0398 (5)
C20	−0.07275 (16)	0.2507 (2)	−0.03992 (15)	0.0455 (6)
H20A	−0.0723	0.2884	−0.0883	0.055*
H20B	−0.1165	0.2979	−0.0202	0.055*
C21	−0.11259 (18)	0.1228 (2)	−0.05729 (15)	0.0527 (6)
H21A	−0.1075	0.0822	−0.0084	0.063*
H21B	−0.0726	0.0776	−0.0817	0.063*
C22	−0.2184 (2)	0.1201 (3)	−0.11039 (17)	0.0689 (8)
H22A	−0.2588	0.1636	−0.0854	0.083*
H22B	−0.2410	0.0360	−0.1180	0.083*

	U11	U22	U33	U12	U13	U23
S1	0.0392 (3)	0.0612 (4)	0.0382 (3)	−0.0085 (3)	0.0118 (3)	−0.0020 (3)
S2	0.0413 (3)	0.0525 (4)	0.0396 (3)	−0.0108 (3)	0.0067 (3)	0.0051 (3)
Cl1	0.0886 (5)	0.0397 (4)	0.0721 (5)	−0.0045 (3)	0.0203 (4)	−0.0071 (3)
Cl2	0.0732 (6)	0.1360 (9)	0.0916 (7)	−0.0178 (6)	−0.0060 (5)	−0.0378 (6)
Cl3	0.0698 (5)	0.0801 (5)	0.0665 (5)	0.0138 (4)	0.0159 (4)	−0.0065 (4)
Cl4	0.0651 (5)	0.0973 (6)	0.0554 (4)	−0.0125 (4)	−0.0066 (4)	0.0048 (4)
O1	0.0387 (9)	0.0765 (12)	0.0466 (10)	−0.0065 (9)	0.0076 (8)	0.0167 (9)
O2	0.0442 (9)	0.0552 (10)	0.0505 (10)	−0.0112 (8)	−0.0018 (8)	0.0148 (9)
N1	0.0307 (9)	0.0449 (11)	0.0362 (10)	−0.0047 (8)	0.0062 (8)	0.0032 (8)
N2	0.0336 (10)	0.0486 (11)	0.0332 (10)	−0.0001 (8)	0.0050 (8)	0.0053 (8)
N3	0.0321 (10)	0.0524 (12)	0.0382 (10)	−0.0086 (8)	0.0031 (8)	0.0081 (9)
N4	0.0333 (9)	0.0435 (10)	0.0326 (9)	−0.0016 (8)	0.0039 (8)	0.0036 (8)
C1	0.0467 (13)	0.0463 (13)	0.0381 (13)	−0.0081 (11)	0.0089 (11)	−0.0007 (10)
C2	0.0508 (15)	0.077 (2)	0.0480 (15)	−0.0241 (15)	0.0033 (13)	−0.0025 (14)
C3	0.0405 (15)	0.104 (3)	0.0628 (19)	−0.0010 (17)	−0.0006 (13)	0.0162 (18)
C4	0.0504 (16)	0.073 (2)	0.072 (2)	0.0178 (15)	0.0067 (15)	0.0119 (16)
C5	0.0520 (15)	0.0462 (14)	0.0574 (16)	0.0027 (12)	0.0095 (13)	0.0021 (12)
C6	0.0350 (11)	0.0460 (13)	0.0337 (11)	−0.0014 (10)	0.0066 (9)	0.0044 (10)
C7	0.0345 (11)	0.0316 (11)	0.0374 (12)	−0.0011 (9)	0.0067 (9)	−0.0026 (9)
C8	0.0360 (12)	0.0510 (14)	0.0399 (13)	−0.0020 (10)	0.0071 (10)	0.0040 (11)
C9	0.0411 (14)	0.087 (2)	0.0479 (15)	−0.0073 (14)	0.0059 (12)	0.0124 (14)
C10	0.0419 (14)	0.093 (2)	0.0562 (17)	0.0013 (14)	0.0129 (13)	0.0058 (16)
C11	0.0378 (14)	0.113 (3)	0.0657 (19)	0.0026 (16)	0.0092 (13)	−0.0008 (18)
C12	0.0416 (13)	0.0552 (15)	0.0441 (14)	−0.0034 (11)	0.0074 (11)	0.0109 (11)
C13	0.0343 (13)	0.0751 (19)	0.0650 (18)	0.0009 (13)	0.0049 (12)	0.0169 (16)
C14	0.0412 (15)	0.084 (2)	0.0635 (19)	−0.0182 (15)	−0.0068 (13)	0.0083 (17)
C15	0.0652 (19)	0.075 (2)	0.0554 (18)	−0.0198 (16)	0.0008 (15)	−0.0108 (15)
C16	0.0448 (14)	0.0633 (17)	0.0530 (16)	−0.0035 (12)	0.0065 (12)	−0.0016 (13)
C17	0.0339 (12)	0.0532 (14)	0.0364 (12)	−0.0063 (10)	0.0024 (10)	0.0096 (11)
C18	0.0302 (10)	0.0407 (12)	0.0327 (11)	0.0019 (9)	0.0066 (9)	−0.0030 (9)
C19	0.0346 (11)	0.0408 (12)	0.0403 (13)	−0.0014 (10)	0.0073 (10)	−0.0017 (10)
C20	0.0321 (11)	0.0481 (14)	0.0492 (14)	−0.0023 (10)	0.0041 (10)	0.0025 (11)
C21	0.0456 (14)	0.0565 (15)	0.0486 (15)	−0.0126 (12)	0.0058 (12)	0.0036 (12)
C22	0.0501 (16)	0.089 (2)	0.0587 (17)	−0.0276 (15)	0.0064 (13)	−0.0009 (16)

S1—C7	1.671 (2)	C5—H5	0.9300
S2—C18	1.673 (2)	C8—C9	1.502 (3)
Cl1—C1	1.727 (3)	C9—C10	1.481 (4)
Cl2—C11	1.758 (3)	C9—H9A	0.9700
Cl3—C12	1.732 (3)	C9—H9B	0.9700
Cl4—C22	1.788 (3)	C10—C11	1.504 (4)
O1—C8	1.217 (3)	C10—H10A	0.9700
O2—C19	1.215 (3)	C10—H10B	0.9700
N1—C7	1.332 (3)	C11—H11A	0.9700
N1—C6	1.429 (3)	C11—H11B	0.9700
N1—H1A	0.8600	C12—C13	1.379 (4)
N2—C8	1.371 (3)	C12—C17	1.386 (3)
N2—C7	1.381 (3)	C13—C14	1.371 (4)
N2—H2A	0.8600	C13—H13	0.9300
N3—C18	1.323 (3)	C14—C15	1.375 (5)
N3—C17	1.423 (3)	C14—H14	0.9300
N3—H3A	0.8600	C15—C16	1.381 (4)
N4—C19	1.376 (3)	C15—H15	0.9300
N4—C18	1.382 (3)	C16—C17	1.377 (4)
N4—H4A	0.8600	C16—H16	0.9300
C1—C6	1.374 (3)	C19—C20	1.499 (3)
C1—C2	1.385 (4)	C20—C21	1.505 (4)
C2—C3	1.371 (5)	C20—H20A	0.9700
C2—H2	0.9300	C20—H20B	0.9700
C3—C4	1.365 (5)	C21—C22	1.507 (4)
C3—H3	0.9300	C21—H21A	0.9700
C4—C5	1.388 (4)	C21—H21B	0.9700
C4—H4	0.9300	C22—H22A	0.9700
C5—C6	1.379 (3)	C22—H22B	0.9700
C7—N1—C6	122.78 (18)	C10—C11—Cl2	112.7 (2)
C7—N1—H1A	118.6	C10—C11—H11A	109.1
C6—N1—H1A	118.6	Cl2—C11—H11A	109.1
C8—N2—C7	128.89 (19)	C10—C11—H11B	109.1
C8—N2—H2A	115.6	Cl2—C11—H11B	109.1
C7—N2—H2A	115.6	H11A—C11—H11B	107.8
C18—N3—C17	122.27 (19)	C13—C12—C17	120.6 (3)
C18—N3—H3A	118.9	C13—C12—Cl3	119.9 (2)
C17—N3—H3A	118.9	C17—C12—Cl3	119.53 (19)
C19—N4—C18	128.30 (19)	C14—C13—C12	119.2 (3)
C19—N4—H4A	115.8	C14—C13—H13	120.4
C18—N4—H4A	115.8	C12—C13—H13	120.4
C6—C1—C2	120.3 (2)	C13—C14—C15	120.8 (3)
C6—C1—Cl1	120.41 (18)	C13—C14—H14	119.6
C2—C1—Cl1	119.3 (2)	C15—C14—H14	119.6
C3—C2—C1	119.5 (3)	C14—C15—C16	120.0 (3)
C3—C2—H2	120.3	C14—C15—H15	120.0
C1—C2—H2	120.3	C16—C15—H15	120.0
C4—C3—C2	120.6 (3)	C17—C16—C15	119.9 (3)
C4—C3—H3	119.7	C17—C16—H16	120.1
C2—C3—H3	119.7	C15—C16—H16	120.1
C3—C4—C5	120.1 (3)	C16—C17—C12	119.6 (2)
C3—C4—H4	120.0	C16—C17—N3	119.9 (2)
C5—C4—H4	120.0	C12—C17—N3	120.5 (2)
C6—C5—C4	119.7 (3)	N3—C18—N4	116.67 (19)
C6—C5—H5	120.2	N3—C18—S2	123.45 (16)
C4—C5—H5	120.2	N4—C18—S2	119.88 (16)
C1—C6—C5	119.8 (2)	O2—C19—N4	122.5 (2)
C1—C6—N1	121.4 (2)	O2—C19—C20	123.3 (2)
C5—C6—N1	118.8 (2)	N4—C19—C20	114.20 (19)
N1—C7—N2	116.99 (19)	C19—C20—C21	113.5 (2)
N1—C7—S1	124.22 (16)	C19—C20—H20A	108.9
N2—C7—S1	118.80 (16)	C21—C20—H20A	108.9
O1—C8—N2	122.7 (2)	C19—C20—H20B	108.9
O1—C8—C9	124.0 (2)	C21—C20—H20B	108.9
N2—C8—C9	113.3 (2)	H20A—C20—H20B	107.7
C10—C9—C8	113.9 (2)	C20—C21—C22	112.7 (2)
C10—C9—H9A	108.8	C20—C21—H21A	109.1
C8—C9—H9A	108.8	C22—C21—H21A	109.1
C10—C9—H9B	108.8	C20—C21—H21B	109.1
C8—C9—H9B	108.8	C22—C21—H21B	109.1
H9A—C9—H9B	107.7	H21A—C21—H21B	107.8
C9—C10—C11	113.9 (2)	C21—C22—Cl4	112.16 (19)
C9—C10—H10A	108.8	C21—C22—H22A	109.2
C11—C10—H10A	108.8	Cl4—C22—H22A	109.2
C9—C10—H10B	108.8	C21—C22—H22B	109.2
C11—C10—H10B	108.8	Cl4—C22—H22B	109.2
H10A—C10—H10B	107.7	H22A—C22—H22B	107.9
C6—C1—C2—C3	1.5 (4)	C17—C12—C13—C14	0.6 (4)
Cl1—C1—C2—C3	−178.0 (2)	Cl3—C12—C13—C14	−178.5 (2)
C1—C2—C3—C4	0.0 (5)	C12—C13—C14—C15	−0.3 (4)
C2—C3—C4—C5	−1.2 (5)	C13—C14—C15—C16	−0.2 (5)
C3—C4—C5—C6	1.0 (5)	C14—C15—C16—C17	0.5 (5)
C2—C1—C6—C5	−1.8 (4)	C15—C16—C17—C12	−0.2 (4)
Cl1—C1—C6—C5	177.8 (2)	C15—C16—C17—N3	178.4 (2)
C2—C1—C6—N1	−179.2 (2)	C13—C12—C17—C16	−0.4 (4)
Cl1—C1—C6—N1	0.4 (3)	Cl3—C12—C17—C16	178.7 (2)
C4—C5—C6—C1	0.5 (4)	C13—C12—C17—N3	−179.0 (2)
C4—C5—C6—N1	178.0 (2)	Cl3—C12—C17—N3	0.1 (3)
C7—N1—C6—C1	−76.9 (3)	C18—N3—C17—C16	89.7 (3)
C7—N1—C6—C5	105.7 (3)	C18—N3—C17—C12	−91.7 (3)
C6—N1—C7—N2	−178.95 (19)	C17—N3—C18—N4	−177.8 (2)
C6—N1—C7—S1	1.4 (3)	C17—N3—C18—S2	1.4 (3)
C8—N2—C7—N1	6.1 (3)	C19—N4—C18—N3	−6.3 (3)
C8—N2—C7—S1	−174.26 (19)	C19—N4—C18—S2	174.38 (18)
C7—N2—C8—O1	−0.9 (4)	C18—N4—C19—O2	−1.8 (4)
C7—N2—C8—C9	180.0 (2)	C18—N4—C19—C20	176.4 (2)
O1—C8—C9—C10	2.1 (4)	O2—C19—C20—C21	−33.5 (3)
N2—C8—C9—C10	−178.8 (3)	N4—C19—C20—C21	148.3 (2)
C8—C9—C10—C11	−177.6 (3)	C19—C20—C21—C22	174.7 (2)
C9—C10—C11—Cl2	−66.2 (4)	C20—C21—C22—Cl4	61.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.01	2.675 (3)	133
N3—H3A···O2	0.86	1.98	2.652 (3)	134
N1—H1A···O2	0.86	2.37	3.070 (3)	138
N3—H3A···O1	0.86	2.37	3.073 (3)	139
N2—H2A···S2i	0.86	2.58	3.404 (2)	160
N4—H4A···S1ii	0.86	2.58	3.433 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	2.01	2.675 (3)	133
N3—H3A⋯O2	0.86	1.98	2.652 (3)	134
N1—H1A⋯O2	0.86	2.37	3.070 (3)	138
N3—H3A⋯O1	0.86	2.37	3.073 (3)	139
N2—H2A⋯S2i	0.86	2.58	3.404 (2)	160
N4—H4A⋯S1ii	0.86	2.58	3.433 (2)	174

Symmetry codes: (i) ; (ii) .