1-(4-Chloro­butano­yl)-3-(2-chloro­phen­yl)thio­urea

Yusof, M.S.M.; Embong, N.F.; Yamin, B.M.; Ngah, N.

doi:10.1107/S160053681201759X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1536

doi:10.1107/S160053681201759X

Open

access

1-(4-Chlorobutanoyl)-3-(2-chlorophenyl)thiourea

M. Sukeri M. Yusof,^a Nur Farhana Embong,^a Bohari M. Yamin ^b and Nurziana Ngah ^c ^*

^aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Menggabang Telipot, 21030 Kuala Terengganu, Malaysia, ^bSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia, and ^cKulliyyah of Science, International Islamic University Malaysia, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia
^*Correspondence e-mail: nurziana@iium.edu.my

(Received 13 April 2012; accepted 20 April 2012; online 25 April 2012)

The asymmetric unit of the title compound, C₁₁H₁₂Cl₂N₂OS, contains two crystallographically independent molecules with different conformations: the benzene ring and the thiourea fragment form dihedral angles of 74.32 (11) and 89.39 (11)°. One amino group in each molecule is involved in intramolecular N—H⋯O and intermolecular N—H⋯O hydrogen bonding: the latter links pairs of independent molecules into dimers. In the crystal, weak N—H⋯S interactions 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_r = 291.19
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.03
4727 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201759X/cv5287sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681201759X/cv5287Isup3.cml

checkCIF report

Comment top

The asymmetric unit of the title compound, (I), contains two crystallographically independent molecules with different conformations. The title molecule is similiar to the previously reported N-(4-chlorobutanoyl)- N'-(2-fluorophenyl)thiourea (Yusof et al., 2011) except the fluorine atom at ortho position of benzene ring is substituted by the chlorine atom at the same position. The bond lengths and angles are in normal ranges (Allen et al., 1987). The benzene [(C1—C6) & (C12—C17)] and thiourea [(N1/N2/C7/S1/C6) & (N3/N4/C18/S2/C17)] fragments are each planar with maximum deviation is 0.047 (2) Å for atom N4 from the mean plane. In each independent molecule, the benzene and thiourea fragments make dihedral angles of 74.32 (11)° and 89.39 (11)°, respectively and comparable to those reported by Yusof et al., (2011). One amino group in each molecule, N1—H1A and N3—H3A, respectively, is involved in bifurcated N—H···O hydrogen-bonding (Table 1) - intra and intermolecular ones, respectively, and the latter ones link two independent molecules into dimer. In the crystal, weak N—H···S interactions (Table 1) link further these dimers into chains propagated along c axis.

Related literature top

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

Experimental top

30 ml Acetone solution of 2-chloroanaline (1.81 g, 14.29 mmol) were added into a round-bottom flask containing a solution of 4-chlorobutanoylchloride (2.00 g, 14.29 mmol) and ammonium thiocyanate (1.10 g, 14.29 mmol). The solution mixture was refluxed for 2.5 h then filtered off and left to evaporate at room temperature. The yellowish precipitate obtained was washed with water and cold ethanol. The yellowish crystals suitable for X-ray analysis were obtained by recrystallization of the precipitate in DMF.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The content of asymmetric unit of the title compound showing the atomic numbering and 40% probability displacement ellipsoids. Dashed lines denote hydrogen bonds.
	Fig. 2. The molecular packing viewed down the b axis. Dashed lines denote N—H···S interactions.

1-(4-Chlorobutanoyl)-3-(2-chlorophenyl)thiourea top

Crystal data top

C₁₁H₁₂Cl₂N₂OS	F(000) = 1200
M_r = 291.19	D_x = 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

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4727 independent reflections
Radiation source: fine-focus sealed tube	3802 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.0°, θ_min = 1.5°
ω scan	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −13→12
T_min = 0.780, T_max = 0.793	l = −16→21
14457 measured reflections

Refinement top

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(F_o²) + (0.0514P)² + 1.5167P] where P = (F_o² + 2F_c²)/3
4727 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₁H₁₂Cl₂N₂OS	V = 2688.0 (9) Å³
M_r = 291.19	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.396 (3) Å	µ = 0.62 mm⁻¹
b = 10.941 (2) Å	T = 298 K
c = 18.093 (4) Å	0.42 × 0.41 × 0.39 mm
β = 109.399 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4727 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3802 reflections with I > 2σ(I)
T_min = 0.780, T_max = 0.793	R_int = 0.023
14457 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.03	Δρ_max = 0.40 e Å⁻³
4727 reflections	Δρ_min = −0.33 e Å⁻³
307 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂Cl₂N₂OS
M_r	291.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.396 (3), 10.941 (2), 18.093 (4)
β (°)	109.399 (4)
V (Å³)	2688.0 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.42 × 0.41 × 0.39

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.780, 0.793
No. of measured, independent and observed [I > 2σ(I)] reflections	14457, 4727, 3802
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.03
No. of reflections	4727
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.33

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Acknowledgements

MSMY, BMY and NN acknowledge Universiti Malaysia Terengganu, Universiti Kebangsaan Malaysia and the International Islamic University Malaysia for facilities and funding to support the synthetic part of this work.

References

Allen, F. H., Kennard, O., watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yusof, M. S. M., Embong, N. F., Othman, E. A. & Yamin, B. M. (2011). Acta Cryst. E67, o1849. Web of Science CSD CrossRef IUCr Journals Google Scholar