1-(3-Chloro­phen­yl)-3-(2,6-dichloro­benzo­yl)thio­urea

Khawar Rauf, M.; Bolte, M.; Rauf, A.

doi:10.1107/S1600536808043444

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o234

doi:10.1107/S1600536808043444

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1-(3-Chlorophenyl)-3-(2,6-dichlorobenzoyl)thiourea

M. Khawar Rauf,^a ^* Michael Bolte ^b and Abdur Rauf ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany, and ^cDepartment of Chemistry, Islamia University of Bahawalpur, Pakistan
^*Correspondence e-mail: khawar_rauf@hotmail.com

(Received 1 December 2008; accepted 20 December 2008; online 8 January 2009)

The structure of the title compound, C₁₄H₉Cl₃N₂OS, is composed of discrete molecules with bond lengths and angles quite typical for thiourea compounds of this class. The plane containing the thiocarbonyl and carbonyl groups subtends dihedral angles of 48.19 (3) and 87.51 (3)° with the planes formed by the 3-chloro and 2,6-dichlorophenyl rings, respectively; the dihedral angle between the two benzene ring planes is 45.32 (3)°. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation and the molecules form intermolecular N—H⋯S and N—H⋯O hydrogen bonds, generating a sheet along the a axis.

Related literature

For related structures, see: Khawar Rauf et al., (2006a ,b ; 2007 ). For a description of the Cambridge structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₄H₉Cl₃N₂OS
M_r = 359.64
Monoclinic, P 2₁ /c
a = 10.6589 (5) Å
b = 11.2114 (5) Å
c = 13.2919 (6) Å
β = 99.942 (3)°
V = 1564.55 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 173 (2) K
0.47 × 0.47 × 0.45 mm

Data collection

Stoe IPDS-II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003 ; Blessing, 1995 ) T_min = 0.729, T_max = 0.739
39690 measured reflections
5066 independent reflections
4674 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.094
S = 1.06
5066 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.82 (2)	2.07 (2)	2.7190 (13)	136.0 (18)
N2—H2⋯O1ⁱ	0.82 (2)	2.37 (2)	3.0749 (14)	145.5 (18)
N1—H1⋯S1ⁱⁱ	0.86 (2)	2.47 (2)	3.2974 (10)	163.6 (18)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: PLATON and SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043444/pv2127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043444/pv2127Isup2.hkl

checkCIF report

Comment top

The background to this study has been set out in our previous work on the structural chemistry of N,N'-disubstituted thioureas (Khawar Rauf et al., 2006a, 2007). Herein, as a continuation of these studies, the structure of the title compound, (I), is described.

In the structure of the title compound (Fig. 1), bond lengths and bond angles can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002) and some related structures (Khawar Rauf et al., 2006b). The molecule exists in the thione form with typical thiourea C—S and C—O bonds, as well as shortened C—N bonds. The thiocarbonyl and carbonyl groups are almost coplanar. The molecule features an intramolecular N—H···O hydrogen bond in the crystal structure. The molecules lying about inversions centers associate via N—H···S intermolecular hydrogen bonds to form dimers on one side and a similar association via N—H···O hydrogen bonding on the other side thus result in a sheet of molecules of (I) along the a<ι>-axis (Table 1; Fig. 2).

Related literature top

For related structures, see: Khawar Rauf et al., (2006a,b; 2007). For a description of the Cambridge structural Database, see: Allen (2002).

Experimental top

Freshly prepared and steam distillated 2,6-dichlorobenzoyl isothiocyanate (2.32 g, 10 mmol) was stirred in acetone (30 ml) for 20 minutes. Neat 3-chloroaniline (1.27 g, 10 mmol) was then added and the resulting mixture was stirred for 1 h. The reaction mixture was then poured into acidified (pH 4) water (approx. 300 ml) and stirred well. The solid product was separated, washed with deionized water and purified by recrystallization from methanol/1,1-dichloromethane (1:10 v/v) to give fine crystals of (I), with an overall yield of 85%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2003) and SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I) showing atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the unit cell of (I) showing hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

1-(3-Chlorophenyl)-3-(2,6-dichlorobenzoyl)thiourea top

Crystal data top

C₁₄H₉Cl₃N₂OS	F(000) = 728
M_r = 359.64	D_x = 1.527 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 37695 reflections
a = 10.6589 (5) Å	θ = 3.7–31.2°
b = 11.2114 (5) Å	µ = 0.72 mm⁻¹
c = 13.2919 (6) Å	T = 173 K
β = 99.942 (3)°	Block, colourless
V = 1564.55 (12) Å³	0.47 × 0.47 × 0.45 mm
Z = 4

Data collection top

Stoe IPDS-II two-circle diffractometer	5066 independent reflections
Radiation source: fine-focus sealed tube	4674 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scans	θ_max = 31.3°, θ_min = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −15→15
T_min = 0.729, T_max = 0.739	k = −16→16
39690 measured reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0404P)² + 0.9365P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
5066 reflections	Δρ_max = 0.65 e Å⁻³
199 parameters	Δρ_min = −0.66 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0111 (12)

Crystal data top

C₁₄H₉Cl₃N₂OS	V = 1564.55 (12) Å³
M_r = 359.64	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6589 (5) Å	µ = 0.72 mm⁻¹
b = 11.2114 (5) Å	T = 173 K
c = 13.2919 (6) Å	0.47 × 0.47 × 0.45 mm
β = 99.942 (3)°

Data collection top

Stoe IPDS-II two-circle diffractometer	5066 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	4674 reflections with I > 2σ(I)
T_min = 0.729, T_max = 0.739	R_int = 0.046
39690 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.65 e Å⁻³
5066 reflections	Δρ_min = −0.66 e Å⁻³
199 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	0.09625 (3)	0.60027 (3)	0.62517 (2)	0.02474 (9)
Cl1	0.19574 (4)	0.61905 (4)	0.23352 (3)	0.03999 (11)
Cl2	0.22323 (4)	0.18815 (4)	0.41908 (3)	0.03969 (11)
Cl3	0.33122 (7)	0.61484 (7)	0.99688 (3)	0.0735 (2)
C1	0.27158 (11)	0.45474 (11)	0.41547 (8)	0.0182 (2)
O1	0.38737 (8)	0.46303 (10)	0.43625 (7)	0.0285 (2)
N1	0.19003 (9)	0.49493 (10)	0.47738 (8)	0.01915 (19)
H1	0.1105 (19)	0.4841 (18)	0.4559 (15)	0.030 (5)*
C2	0.21866 (10)	0.55197 (10)	0.57210 (8)	0.0174 (2)
N2	0.34238 (9)	0.56439 (10)	0.61243 (8)	0.01918 (19)
H2	0.394 (2)	0.5442 (19)	0.5770 (15)	0.032 (5)*
C11	0.20320 (10)	0.39859 (11)	0.31773 (8)	0.0179 (2)
C12	0.16489 (13)	0.46736 (13)	0.23029 (10)	0.0251 (2)
C13	0.09985 (17)	0.41613 (18)	0.14040 (11)	0.0394 (4)
H13	0.0745	0.4639	0.0814	0.047*
C14	0.07264 (17)	0.29526 (19)	0.13789 (12)	0.0421 (4)
H14	0.0275	0.2606	0.0770	0.051*
C15	0.11043 (15)	0.22420 (15)	0.22299 (12)	0.0337 (3)
H15	0.0923	0.1412	0.2208	0.040*
C16	0.17558 (12)	0.27683 (12)	0.31200 (10)	0.0232 (2)
C21	0.39003 (11)	0.62132 (11)	0.70818 (9)	0.0195 (2)
C22	0.34464 (15)	0.58955 (14)	0.79662 (10)	0.0289 (3)
H22	0.2822	0.5288	0.7953	0.035*
C23	0.39279 (16)	0.64880 (16)	0.88702 (10)	0.0340 (3)
C24	0.48645 (15)	0.73570 (15)	0.89168 (11)	0.0332 (3)
H24	0.5180	0.7752	0.9541	0.040*
C25	0.53305 (14)	0.76367 (15)	0.80313 (11)	0.0318 (3)
H25	0.5984	0.8218	0.8053	0.038*
C26	0.48479 (12)	0.70721 (13)	0.71106 (10)	0.0246 (2)
H26	0.5164	0.7273	0.6507	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01676 (13)	0.03383 (17)	0.02412 (15)	−0.00159 (11)	0.00495 (10)	−0.01452 (12)
Cl1	0.0485 (2)	0.02974 (18)	0.0415 (2)	−0.00112 (15)	0.00718 (16)	0.00931 (14)
Cl2	0.0507 (2)	0.02793 (17)	0.0402 (2)	0.00109 (15)	0.00724 (16)	0.00754 (14)
Cl3	0.1095 (5)	0.0945 (5)	0.02015 (18)	−0.0585 (4)	0.0216 (2)	−0.0165 (2)
C1	0.0160 (4)	0.0228 (5)	0.0156 (4)	0.0010 (4)	0.0018 (4)	−0.0044 (4)
O1	0.0144 (4)	0.0461 (6)	0.0246 (4)	0.0004 (4)	0.0023 (3)	−0.0134 (4)
N1	0.0133 (4)	0.0275 (5)	0.0163 (4)	−0.0008 (3)	0.0016 (3)	−0.0081 (4)
C2	0.0171 (5)	0.0197 (5)	0.0152 (4)	−0.0009 (4)	0.0018 (4)	−0.0037 (4)
N2	0.0153 (4)	0.0266 (5)	0.0152 (4)	−0.0008 (4)	0.0015 (3)	−0.0061 (4)
C11	0.0160 (4)	0.0231 (5)	0.0147 (4)	−0.0007 (4)	0.0030 (4)	−0.0051 (4)
C12	0.0247 (6)	0.0317 (6)	0.0185 (5)	−0.0009 (5)	0.0023 (4)	0.0000 (4)
C13	0.0408 (8)	0.0571 (10)	0.0173 (6)	−0.0037 (7)	−0.0037 (5)	−0.0014 (6)
C14	0.0391 (8)	0.0612 (11)	0.0243 (6)	−0.0127 (8)	0.0002 (6)	−0.0189 (7)
C15	0.0315 (7)	0.0355 (7)	0.0350 (7)	−0.0098 (6)	0.0080 (5)	−0.0185 (6)
C16	0.0225 (5)	0.0246 (6)	0.0236 (5)	−0.0020 (4)	0.0070 (4)	−0.0059 (4)
C21	0.0185 (5)	0.0235 (5)	0.0151 (4)	−0.0003 (4)	−0.0005 (4)	−0.0049 (4)
C22	0.0358 (7)	0.0330 (7)	0.0168 (5)	−0.0123 (5)	0.0015 (5)	−0.0041 (5)
C23	0.0446 (8)	0.0414 (8)	0.0156 (5)	−0.0123 (7)	0.0041 (5)	−0.0064 (5)
C24	0.0341 (7)	0.0410 (8)	0.0222 (6)	−0.0079 (6)	−0.0016 (5)	−0.0123 (5)
C25	0.0265 (6)	0.0382 (8)	0.0300 (6)	−0.0108 (5)	0.0027 (5)	−0.0129 (6)
C26	0.0206 (5)	0.0305 (6)	0.0229 (5)	−0.0044 (5)	0.0038 (4)	−0.0076 (5)

Geometric parameters (Å, º) top

S1—C2	1.6766 (12)	C13—H13	0.9500
Cl1—C12	1.7313 (15)	C14—C15	1.385 (3)
Cl2—C16	1.7386 (14)	C14—H14	0.9500
Cl3—C23	1.7433 (15)	C15—C16	1.3951 (18)
C1—O1	1.2209 (14)	C15—H15	0.9500
C1—N1	1.3721 (14)	C21—C26	1.3912 (18)
C1—C11	1.5128 (15)	C21—C22	1.3925 (18)
N1—C2	1.3980 (14)	C22—C23	1.3912 (18)
N1—H1	0.86 (2)	C22—H22	0.9500
C2—N2	1.3423 (14)	C23—C24	1.389 (2)
N2—C21	1.4360 (14)	C24—C25	1.390 (2)
N2—H2	0.82 (2)	C24—H24	0.9500
C11—C12	1.3957 (17)	C25—C26	1.3947 (17)
C11—C16	1.3957 (17)	C25—H25	0.9500
C12—C13	1.3971 (19)	C26—H26	0.9500
C13—C14	1.385 (3)

O1—C1—N1	124.03 (10)	C14—C15—C16	118.77 (14)
O1—C1—C11	122.98 (10)	C14—C15—H15	120.6
N1—C1—C11	112.99 (9)	C16—C15—H15	120.6
C1—N1—C2	128.90 (10)	C15—C16—C11	121.96 (13)
C1—N1—H1	116.6 (13)	C15—C16—Cl2	118.99 (11)
C2—N1—H1	114.5 (13)	C11—C16—Cl2	119.05 (9)
N2—C2—N1	116.98 (10)	C26—C21—C22	120.68 (11)
N2—C2—S1	125.50 (9)	C26—C21—N2	118.43 (11)
N1—C2—S1	117.52 (8)	C22—C21—N2	120.88 (11)
C2—N2—C21	124.95 (10)	C23—C22—C21	118.48 (13)
C2—N2—H2	117.2 (14)	C23—C22—H22	120.8
C21—N2—H2	117.5 (14)	C21—C22—H22	120.8
C12—C11—C16	117.79 (11)	C24—C23—C22	121.91 (13)
C12—C11—C1	120.90 (11)	C24—C23—Cl3	119.18 (10)
C16—C11—C1	121.31 (11)	C22—C23—Cl3	118.89 (12)
C11—C12—C13	121.04 (14)	C23—C24—C25	118.67 (12)
C11—C12—Cl1	119.67 (10)	C23—C24—H24	120.7
C13—C12—Cl1	119.28 (12)	C25—C24—H24	120.7
C14—C13—C12	119.59 (15)	C24—C25—C26	120.60 (13)
C14—C13—H13	120.2	C24—C25—H25	119.7
C12—C13—H13	120.2	C26—C25—H25	119.7
C13—C14—C15	120.85 (13)	C21—C26—C25	119.62 (12)
C13—C14—H14	119.6	C21—C26—H26	120.2
C15—C14—H14	119.6	C25—C26—H26	120.2

O1—C1—N1—C2	0.6 (2)	C14—C15—C16—C11	0.2 (2)
C11—C1—N1—C2	−179.35 (12)	C14—C15—C16—Cl2	179.98 (12)
C1—N1—C2—N2	−4.11 (19)	C12—C11—C16—C15	−0.86 (18)
C1—N1—C2—S1	175.27 (11)	C1—C11—C16—C15	178.74 (12)
N1—C2—N2—C21	179.40 (11)	C12—C11—C16—Cl2	179.39 (9)
S1—C2—N2—C21	0.07 (18)	C1—C11—C16—Cl2	−1.01 (16)
O1—C1—C11—C12	−90.46 (16)	C2—N2—C21—C26	−130.55 (14)
N1—C1—C11—C12	89.48 (14)	C2—N2—C21—C22	50.86 (18)
O1—C1—C11—C16	89.95 (16)	C26—C21—C22—C23	2.4 (2)
N1—C1—C11—C16	−90.11 (14)	N2—C21—C22—C23	−179.07 (14)
C16—C11—C12—C13	0.68 (19)	C21—C22—C23—C24	−1.7 (3)
C1—C11—C12—C13	−178.93 (13)	C21—C22—C23—Cl3	176.96 (13)
C16—C11—C12—Cl1	179.53 (10)	C22—C23—C24—C25	−0.1 (3)
C1—C11—C12—Cl1	−0.07 (16)	Cl3—C23—C24—C25	−178.76 (14)
C11—C12—C13—C14	0.1 (2)	C23—C24—C25—C26	1.3 (3)
Cl1—C12—C13—C14	−178.73 (14)	C22—C21—C26—C25	−1.2 (2)
C12—C13—C14—C15	−0.8 (3)	N2—C21—C26—C25	−179.82 (13)
C13—C14—C15—C16	0.6 (2)	C24—C25—C26—C21	−0.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.82 (2)	2.07 (2)	2.7190 (13)	136.0 (18)
N2—H2···O1ⁱ	0.82 (2)	2.37 (2)	3.0749 (14)	145.5 (18)
N1—H1···S1ⁱⁱ	0.86 (2)	2.47 (2)	3.2974 (10)	163.6 (18)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₉Cl₃N₂OS
M_r	359.64
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	10.6589 (5), 11.2114 (5), 13.2919 (6)
β (°)	99.942 (3)
V (Å³)	1564.55 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.47 × 0.47 × 0.45

Data collection
Diffractometer	Stoe IPDS-II two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.729, 0.739
No. of measured, independent and observed [I > 2σ(I)] reflections	39690, 5066, 4674
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.731

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.094, 1.06
No. of reflections	5066
No. of parameters	199
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.66

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 2008), PLATON (Spek, 2003) and SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.82 (2)	2.07 (2)	2.7190 (13)	136.0 (18)
N2—H2···O1ⁱ	0.82 (2)	2.37 (2)	3.0749 (14)	145.5 (18)
N1—H1···S1ⁱⁱ	0.86 (2)	2.47 (2)	3.2974 (10)	163.6 (18)

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

Acknowledgements

MKR is grateful to the HEC-Pakistan for financial support for the PhD program under scholarship No. [ILC–0363104].

References

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