1-Benzoyl-3-(4-chloro­phen­yl)thio­urea dichloro­methane hemisolvate

Selvakumaran, N.; Sheeba, M.M.; Karvembu, R.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812045588

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3313

doi:10.1107/S1600536812045588

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1-Benzoyl-3-(4-chlorophenyl)thiourea dichloromethane hemisolvate

N. Selvakumaran,^a M. Mary Sheeba,^a R. Karvembu,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 4 November 2012; accepted 5 November 2012; online 10 November 2012)

In the title hemisolvate, C₁₄H₁₁ClN₂OS·0.5CH₂Cl₂, an anti disposition is found for the thione and ketone atoms, as well as the N—H H atoms; the dichloromethane C atom lies on a twofold axis. The central chromophore (including the two adjacent ipso C atoms) is planar (r.m.s. deviation = 0.021 Å) owing to the presence of an intramolecular N—H⋯O hydrogen bond, which closes an S(6) loop. Significant twists are evident in the molecule, the dihedral angles between the central moiety and the phenyl and benzene rings being 29.52 (7) and 40.02 (7)°, respectively. In the crystal, eight-membered {⋯HNC= S}₂ synthons with twofold symmetry form via N—H⋯S hydrogen bonds. The dimers are connected into a supramolecular chain along [111] by C—H⋯O interactions. The chains stack along the c axis, forming columns which define channels in which the occluded dichloromethane molecules reside.

Related literature

For complexation of N-benzoyl-N′-arylthiourea derivatives to transition metals, see: Selvakumaran et al. (2011 ). For related structures, see: Khawar Rauf et al. (2006 ); Selvakumaran et al. (2012 ).

Experimental

Crystal data

C₁₄H₁₁ClN₂OS·0.5CH₂Cl₂
M_r = 333.23
Monoclinic, C 2/c
a = 20.0800 (4) Å
b = 16.0136 (2) Å
c = 10.3752 (2) Å
β = 117.690 (3)°
V = 2954.10 (9) Å³
Z = 8
Cu Kα radiation
μ = 5.26 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.619, T_max = 1.000
5766 measured reflections
2937 independent reflections
2802 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.090
S = 1.05
2937 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O1	0.90 (2)	1.85 (2)	2.6034 (17)	140.6 (18)
N1—H1n⋯S1ⁱ	0.87 (2)	2.59 (2)	3.4368 (15)	167 (2)
C12—H12⋯O1ⁱⁱ	0.95	2.47	3.3743 (19)	160
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2012); 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 ), DIAMOND (Brandenburg, 2006 ) and Qmol (Gans & Shalloway, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812045588/hg5268sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045588/hg5268Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812045588/hg5268Isup3.cml

checkCIF report

Comment top

As part of continuing studies of N-benzoyl-N'-arylthiourea derivatives (Selvakumaran et al., 2012) and their coordination to transition metals such as Pd^II (Selvakumaran et al., 2011), the title compound (I) was investigated as its dichloromethane hemi-solvate. The structure of the unsolvated form is available for comparison (Khawar Rauf et al., 2006).

In (I), Fig. 1, anti dispositions are found for the thione and ketone atoms, and for the N—H H-atoms. The central chromophore (including the two adjacent ipso C atoms) is planar with a r.m.s. deviation of 0.021 Å [maximum deviations of 0.033 (1) Å for N1, and -0.023 (1) Å for S1] owing to the presence of an intramolecular N—H···O hydrogen bond which closes an S(6) loop, Table 1. The observed disposition of atoms is the same as for the unsolvated form (Khawar Rauf et al., 2006).

A significant twist is evident in (I) as seen in the dihedral angles of 29.52 (7) and 40.02 (7)° formed between the central moiety and the C1-phenyl and C9-benzene rings, respectively. The dihedral angle between the six-membered rings is 11.11 (9)°. This pattern of dihedral angles contrasts the situation for the unsolvated form where the comparable dihedral angles are 41.42 (8), 2.77 (8) and 43.93 (10)°, respectively, indicating a significantly greater twist in the molecule as highlighted in the overlay diagram, Fig. 2.

Eight-membered {···HNC═S}₂ synthons (2-fold symmetry) feature in the crystal packing which arise via N—H···S hydrogen bonds and these are connected into a supramolecular chain along [111] by C—H···O interactions which stabilize centrosymmetric 18-membered {···OCNCNC₃H}₂ synthons., Fig. 3 and Table 1. Chains stack along the c axis to form columns which define channels in which the occluded dichloromethane molecules (with 2-fold axis symmetry) reside. There are no specific interactions between the chains nor with the solvent molecules, Fig. 4.

Related literature top

For complexation of N-benzoyl-N'-arylthiourea derivatives to transition metals, see: Selvakumaran et al. (2011). For related structures, see: Khawar Rauf et al. (2006); Selvakumaran et al. (2012).

Experimental top

A solution of benzoyl chloride (0.005 mol, 0.7029 g) in acetone (30 ml) was added drop wise to a suspension of potassium thiocyanate (0.005 mol, 0.4859 g) in anhydrous acetone (30 ml). The reaction mixture was heated under reflux for 45 minutes and then cooled to room temperature. A solution of '4-chloroaniline (0.005 mol, 0.6379 g) in acetone (30 ml) was added and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 300 ml) was added and resulting solid was filtered, washed with water and dried in vacuo. The resulting solid product (78% yield) was recrystallized as colourless blocks from its ethanol/dichloromethane (1:2 ratio) solution. Characterization (dried sample): M.pt: 411 K, Anal. Calcd. For C₁₄H₁₁ClN₂O₂S (%): C, 57.8; H, 3.81; N, 9.63; Found: C, 57.5; H, 4.0; N, 9.8. ¹H NMR: δ (400 MHz, CDCl₃, p.p.m.): 7.35–7.88 (m, 9H); 9.14 (s, 1H, thiourea NH); 12.58 (s, 1H, amide NH). ¹³C NMR: δ (400 MHz, CDCl₃, p.p.m.): 125.3; 127.5; 129.0; 129.2; 131.4; 132.1; 133.8; 136.1; 167.0; 178.4. IR (KBr, cm^-1): 3230 ν(amide N–H), 3028 ν(thiourea N–H), 1688 ν(C=O), 1262 ν(C=S).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 70% probability level. The dichloromethane molecule of solvation has been omitted.
	Fig. 2. Overlay diagram of N-benzoyl-N'-arylthiourea derivative (I) with the unsolvated form (blue). The NSN atoms have been superimposed.
	Fig. 3. A view of the supramolecular chain along [111] in (I). The N—H···S and C—H···O interactions are shown as orange and blue dashed lines, respectively.
	Fig. 4. A view of the unit-cell contents in projection down the c axis in (I). The N—H···S and C—H···O interactions are shown as orange and blue dashed lines, respectively.

1-Benzoyl-3-(4-chlorophenyl)thiourea dichloromethane hemisolvate top

Crystal data top

C₁₄H₁₁ClN₂OS·0.5CH₂Cl₂	F(000) = 1368
M_r = 333.23	D_x = 1.498 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 3963 reflections
a = 20.0800 (4) Å	θ = 3.7–74.2°
b = 16.0136 (2) Å	µ = 5.26 mm⁻¹
c = 10.3752 (2) Å	T = 100 K
β = 117.690 (3)°	Block, colourless
V = 2954.10 (9) Å³	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2937 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2802 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.013
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.4°, θ_min = 3.7°
ω scan	h = −19→24
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −19→18
T_min = 0.619, T_max = 1.000	l = −12→8
5766 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0515P)² + 3.8195P] where P = (F_o² + 2F_c²)/3
2937 reflections	(Δ/σ)_max = 0.001
194 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₄H₁₁ClN₂OS·0.5CH₂Cl₂	V = 2954.10 (9) Å³
M_r = 333.23	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 20.0800 (4) Å	µ = 5.26 mm⁻¹
b = 16.0136 (2) Å	T = 100 K
c = 10.3752 (2) Å	0.30 × 0.25 × 0.20 mm
β = 117.690 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2937 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2802 reflections with I > 2σ(I)
T_min = 0.619, T_max = 1.000	R_int = 0.013
5766 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.32 e Å⁻³
2937 reflections	Δρ_min = −0.63 e Å⁻³
194 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	Occ. (<1)
Cl1	0.64817 (3)	0.24103 (3)	1.38168 (4)	0.02772 (13)
Cl2	0.06334 (3)	0.49157 (3)	0.21781 (6)	0.04144 (16)
S1	0.34276 (2)	0.21105 (2)	0.68579 (4)	0.01812 (12)
O1	0.40404 (6)	0.47474 (7)	0.61554 (12)	0.0182 (2)
N2	0.43155 (7)	0.34562 (8)	0.78527 (14)	0.0141 (3)
N1	0.33686 (7)	0.35253 (8)	0.54885 (14)	0.0139 (3)
C1	0.30153 (8)	0.46811 (10)	0.37713 (17)	0.0142 (3)
C2	0.26545 (9)	0.41884 (10)	0.25243 (17)	0.0161 (3)
H2	0.2727	0.3601	0.2585	0.019*
C3	0.21909 (9)	0.45587 (11)	0.11989 (18)	0.0196 (3)
H3	0.1946	0.4224	0.0350	0.024*
C4	0.20837 (9)	0.54186 (11)	0.11089 (18)	0.0210 (3)
H4	0.1760	0.5669	0.0201	0.025*
C5	0.24478 (9)	0.59118 (11)	0.23394 (19)	0.0199 (3)
H5	0.2374	0.6499	0.2271	0.024*
C6	0.29191 (9)	0.55510 (10)	0.36699 (18)	0.0166 (3)
H6	0.3176	0.5891	0.4509	0.020*
C7	0.35206 (8)	0.43302 (10)	0.52309 (17)	0.0143 (3)
C8	0.37385 (8)	0.30647 (10)	0.67746 (17)	0.0135 (3)
C9	0.48080 (8)	0.31534 (10)	0.92652 (17)	0.0136 (3)
C10	0.50405 (8)	0.37306 (10)	1.03984 (17)	0.0151 (3)
H10	0.4840	0.4280	1.0210	0.018*
C12	0.55623 (9)	0.35074 (10)	1.17967 (17)	0.0166 (3)
H12	0.5727	0.3901	1.2568	0.020*
C13	0.58394 (9)	0.26988 (11)	1.20494 (18)	0.0172 (3)
C14	0.56186 (9)	0.21168 (10)	1.09322 (18)	0.0179 (3)
H14	0.5820	0.1567	1.1126	0.021*
C15	0.51002 (9)	0.23468 (10)	0.95287 (17)	0.0156 (3)
H15	0.4946	0.1956	0.8754	0.019*
C16	0.0000	0.5521 (2)	0.2500	0.090 (2)
H16A	−0.0286	0.5885	0.1647	0.108*	0.50
H16B	0.0286	0.5885	0.3353	0.108*	0.50
H1n	0.2952 (13)	0.3301 (14)	0.485 (2)	0.026 (6)*
H2n	0.4380 (12)	0.3990 (15)	0.767 (2)	0.029 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0299 (2)	0.0251 (2)	0.0164 (2)	0.00383 (17)	0.00079 (18)	0.00311 (15)
Cl2	0.0391 (3)	0.0343 (3)	0.0530 (3)	0.0115 (2)	0.0232 (3)	0.0051 (2)
S1	0.0128 (2)	0.0128 (2)	0.0220 (2)	−0.00272 (13)	0.00228 (16)	0.00305 (14)
O1	0.0162 (5)	0.0142 (5)	0.0196 (6)	−0.0034 (4)	0.0045 (5)	−0.0006 (4)
N2	0.0115 (6)	0.0118 (6)	0.0156 (7)	−0.0008 (5)	0.0035 (5)	0.0006 (5)
N1	0.0102 (6)	0.0128 (6)	0.0148 (6)	−0.0013 (5)	0.0027 (5)	−0.0001 (5)
C1	0.0112 (7)	0.0156 (7)	0.0169 (7)	−0.0007 (6)	0.0074 (6)	0.0012 (6)
C2	0.0147 (7)	0.0155 (7)	0.0197 (8)	−0.0019 (6)	0.0096 (6)	−0.0003 (6)
C3	0.0186 (8)	0.0237 (8)	0.0168 (8)	−0.0034 (7)	0.0084 (6)	−0.0018 (7)
C4	0.0182 (8)	0.0254 (9)	0.0186 (8)	0.0022 (7)	0.0079 (7)	0.0078 (7)
C5	0.0189 (8)	0.0163 (8)	0.0264 (8)	0.0017 (6)	0.0123 (7)	0.0057 (7)
C6	0.0157 (7)	0.0150 (7)	0.0199 (8)	−0.0012 (6)	0.0090 (6)	0.0001 (6)
C7	0.0122 (7)	0.0133 (7)	0.0181 (7)	0.0009 (6)	0.0077 (6)	0.0000 (6)
C8	0.0102 (7)	0.0132 (7)	0.0172 (8)	0.0015 (6)	0.0065 (6)	0.0010 (6)
C9	0.0091 (7)	0.0153 (7)	0.0158 (7)	−0.0006 (6)	0.0051 (6)	0.0009 (6)
C10	0.0134 (7)	0.0127 (7)	0.0198 (8)	−0.0006 (6)	0.0082 (6)	−0.0003 (6)
C12	0.0153 (7)	0.0172 (8)	0.0174 (8)	−0.0032 (6)	0.0077 (6)	−0.0035 (6)
C13	0.0140 (7)	0.0198 (8)	0.0152 (7)	−0.0003 (6)	0.0047 (6)	0.0023 (6)
C14	0.0154 (8)	0.0139 (8)	0.0217 (8)	0.0015 (6)	0.0065 (7)	0.0014 (6)
C15	0.0130 (7)	0.0143 (7)	0.0175 (8)	−0.0004 (6)	0.0054 (6)	−0.0021 (6)
C16	0.077 (3)	0.0225 (16)	0.218 (7)	0.000	0.110 (4)	0.000

Geometric parameters (Å, º) top

Cl1—C13	1.7439 (16)	C4—H4	0.9500
Cl2—C16	1.750 (2)	C5—C6	1.386 (2)
S1—C8	1.6679 (16)	C5—H5	0.9500
O1—C7	1.2350 (19)	C6—H6	0.9500
N2—C8	1.335 (2)	C9—C15	1.392 (2)
N2—C9	1.419 (2)	C9—C10	1.395 (2)
N2—H2n	0.90 (2)	C10—C12	1.385 (2)
N1—C7	1.379 (2)	C10—H10	0.9500
N1—C8	1.398 (2)	C12—C13	1.385 (2)
N1—H1n	0.87 (2)	C12—H12	0.9500
C1—C2	1.396 (2)	C13—C14	1.390 (2)
C1—C6	1.403 (2)	C14—C15	1.390 (2)
C1—C7	1.487 (2)	C14—H14	0.9500
C2—C3	1.385 (2)	C15—H15	0.9500
C2—H2	0.9500	C16—Cl2ⁱ	1.750 (2)
C3—C4	1.390 (2)	C16—H16A	0.9900
C3—H3	0.9500	C16—H16B	0.9900
C4—C5	1.386 (3)

C8—N2—C9	128.44 (14)	N2—C8—N1	114.91 (13)
C8—N2—H2n	115.0 (14)	N2—C8—S1	125.93 (12)
C9—N2—H2n	116.4 (14)	N1—C8—S1	119.15 (11)
C7—N1—C8	127.64 (13)	C15—C9—C10	120.27 (14)
C7—N1—H1n	117.6 (15)	C15—C9—N2	123.21 (14)
C8—N1—H1n	113.8 (15)	C10—C9—N2	116.34 (14)
C2—C1—C6	119.81 (15)	C12—C10—C9	120.40 (15)
C2—C1—C7	123.01 (14)	C12—C10—H10	119.8
C6—C1—C7	117.16 (14)	C9—C10—H10	119.8
C3—C2—C1	119.86 (15)	C10—C12—C13	118.77 (15)
C3—C2—H2	120.1	C10—C12—H12	120.6
C1—C2—H2	120.1	C13—C12—H12	120.6
C2—C3—C4	120.15 (15)	C12—C13—C14	121.64 (15)
C2—C3—H3	119.9	C12—C13—Cl1	118.83 (13)
C4—C3—H3	119.9	C14—C13—Cl1	119.53 (13)
C5—C4—C3	120.25 (15)	C13—C14—C15	119.32 (15)
C5—C4—H4	119.9	C13—C14—H14	120.3
C3—C4—H4	119.9	C15—C14—H14	120.3
C4—C5—C6	120.24 (15)	C14—C15—C9	119.59 (15)
C4—C5—H5	119.9	C14—C15—H15	120.2
C6—C5—H5	119.9	C9—C15—H15	120.2
C5—C6—C1	119.67 (15)	Cl2—C16—Cl2ⁱ	112.8 (2)
C5—C6—H6	120.2	Cl2—C16—H16A	109.0
C1—C6—H6	120.2	Cl2ⁱ—C16—H16A	109.0
O1—C7—N1	122.58 (14)	Cl2—C16—H16B	109.0
O1—C7—C1	121.13 (14)	Cl2ⁱ—C16—H16B	109.0
N1—C7—C1	116.29 (13)	H16A—C16—H16B	107.8

C6—C1—C2—C3	−1.4 (2)	C9—N2—C8—S1	2.8 (2)
C7—C1—C2—C3	179.99 (14)	C7—N1—C8—N2	−1.7 (2)
C1—C2—C3—C4	−0.1 (2)	C7—N1—C8—S1	177.10 (12)
C2—C3—C4—C5	0.9 (2)	C8—N2—C9—C15	41.7 (2)
C3—C4—C5—C6	−0.3 (2)	C8—N2—C9—C10	−143.19 (16)
C4—C5—C6—C1	−1.2 (2)	C15—C9—C10—C12	−0.2 (2)
C2—C1—C6—C5	2.0 (2)	N2—C9—C10—C12	−175.41 (13)
C7—C1—C6—C5	−179.27 (14)	C9—C10—C12—C13	−0.9 (2)
C8—N1—C7—O1	1.6 (2)	C10—C12—C13—C14	1.4 (2)
C8—N1—C7—C1	−177.64 (14)	C10—C12—C13—Cl1	−178.67 (12)
C2—C1—C7—O1	151.52 (15)	C12—C13—C14—C15	−0.8 (2)
C6—C1—C7—O1	−27.2 (2)	Cl1—C13—C14—C15	179.28 (12)
C2—C1—C7—N1	−29.2 (2)	C13—C14—C15—C9	−0.3 (2)
C6—C1—C7—N1	152.07 (14)	C10—C9—C15—C14	0.8 (2)
C9—N2—C8—N1	−178.51 (14)	N2—C9—C15—C14	175.69 (14)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O1	0.90 (2)	1.85 (2)	2.6034 (17)	140.6 (18)
N1—H1n···S1ⁱⁱ	0.87 (2)	2.59 (2)	3.4368 (15)	167 (2)
C12—H12···O1ⁱⁱⁱ	0.95	2.47	3.3743 (19)	160

Symmetry codes: (ii) −x+1/2, −y+1/2, −z+1; (iii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂OS·0.5CH₂Cl₂
M_r	333.23
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	20.0800 (4), 16.0136 (2), 10.3752 (2)
β (°)	117.690 (3)
V (Å³)	2954.10 (9)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	5.26
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.619, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5766, 2937, 2802
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.090, 1.05
No. of reflections	2937
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.63

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O1	0.90 (2)	1.85 (2)	2.6034 (17)	140.6 (18)
N1—H1n···S1ⁱ	0.87 (2)	2.59 (2)	3.4368 (15)	167 (2)
C12—H12···O1ⁱⁱ	0.95	2.47	3.3743 (19)	160

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, −z+2.

Footnotes

‡Additional correspondence author, e-mail: kar@nitt.edu.

Acknowledgements

NS thanks NITT for a Fellowship. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

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