1-(4-Chloro-benzo-yl)-3-(3-methyl-pyridin-2-yl)thio-urea.

The mol-ecule of the title compound, C(14)H(12)ClN(3)OS, consists of three approximately planar fragments: the central thio-urea group, the chloro-phenyl group and the picolyl (3-methyl-pyridin-2-yl) group with a maximum of 0.035 (2)° for an N atom from the mean square plane of the central thiourea group. The central fragment forms dihedral angles of 33.30 (8) and 76.78 (8)° with the chloro-phenyl and picolyl groups, respectively. With respect to the thio-urea C-N bonds, the 4-chloro-benzoyl group is positioned trans to the thiono S atoms, whereas the picolyl group lies in a cis position to it. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by inter-molecular C-H⋯N hydrogen bonds, forming chains along the a axis.

Related literature

For applications of thio­urea derivatives, see: Cunha et al. (2007 ▶); Srivastava et al. (2010 ▶); Manjula et al. (2009 ▶); Chen et al. (2006 ▶). For related structures, see: Estévez-Hernández et al. (2009 ▶); Binzet et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12ClN3OS

M = 305.78

Monoclinic,

a = 7.8417 (15) Å

b = 7.1058 (13) Å

c = 25.585 (5) Å

β = 93.405 (4)°

V = 1423.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 298 K

0.44 × 0.31 × 0.14 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.839, T max = 0.944

9917 measured reflections

3421 independent reflections

2188 reflections with I > 2/s(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.139

S = 1.04

3421 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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/S1600536811032375/yk2015sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032375/yk2015Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032375/yk2015Isup3.cml

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

C14H12ClN3OS	F(000) = 632
Mr = 305.78	Dx = 1.427 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 699 reflections
a = 7.8417 (15) Å	θ = 1.6–28.0°
b = 7.1058 (13) Å	µ = 0.41 mm−1
c = 25.585 (5) Å	T = 298 K
β = 93.405 (4)°	Slab, colourless
V = 1423.1 (5) Å3	0.44 × 0.31 × 0.14 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3421 independent reflections
Radiation source: fine-focus sealed tube	2188 reflections with I > 2/s(I)
graphite	Rint = 0.030
Detector resolution: 83.66 pixels mm-1	θmax = 28.0°, θmin = 1.6°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2003)	k = −9→9
Tmin = 0.839, Tmax = 0.944	l = −30→33
9917 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0722P)2 + 0.0755P] where P = (Fo2 + 2Fc2)/3
3421 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.17 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
Cl1	1.21606 (9)	0.54075 (13)	0.35489 (3)	0.0897 (3)
S1	0.45565 (8)	0.34425 (9)	0.08001 (2)	0.0597 (2)
O1	0.4546 (2)	0.6680 (3)	0.23221 (6)	0.0657 (5)
N1	0.5639 (2)	0.4758 (3)	0.17178 (7)	0.0496 (5)
H1A	0.6480	0.4014	0.1669	0.060*
N2	0.3126 (2)	0.6067 (3)	0.13694 (7)	0.0501 (5)
H2A	0.3116	0.6688	0.1658	0.060*
N3	0.0289 (2)	0.5707 (3)	0.10740 (8)	0.0604 (5)
C2	0.8891 (3)	0.5112 (3)	0.23027 (9)	0.0485 (5)
H2B	0.8932	0.4886	0.1946	0.058*
C3	1.0381 (3)	0.5047 (3)	0.26218 (10)	0.0537 (6)
H3A	1.1421	0.4772	0.2483	0.064*
C4	1.0291 (3)	0.5398 (3)	0.31489 (9)	0.0552 (6)
C5	0.8769 (3)	0.5791 (3)	0.33639 (9)	0.0582 (6)
H5A	0.8734	0.6016	0.3721	0.070*
C6	0.7299 (3)	0.5850 (3)	0.30452 (8)	0.0537 (6)
H6A	0.6264	0.6120	0.3188	0.064*
C1	0.7344 (3)	0.5511 (3)	0.25111 (8)	0.0429 (5)
C7	0.5720 (3)	0.5711 (3)	0.21855 (8)	0.0465 (5)
C8	0.4375 (3)	0.4836 (3)	0.13118 (8)	0.0446 (5)
C9	0.1793 (3)	0.6406 (3)	0.09725 (8)	0.0437 (5)
C10	−0.0985 (3)	0.6033 (4)	0.07152 (12)	0.0758 (8)
H10A	−0.2062	0.5565	0.0777	0.091*
C11	−0.0802 (4)	0.7006 (4)	0.02671 (12)	0.0784 (9)
H11A	−0.1723	0.7180	0.0026	0.094*
C12	0.0767 (4)	0.7723 (4)	0.01786 (10)	0.0689 (7)
H12A	0.0919	0.8398	−0.0127	0.083*
C13	0.2135 (3)	0.7461 (3)	0.05369 (8)	0.0508 (5)
C14	0.3859 (4)	0.8282 (4)	0.04571 (12)	0.0781 (8)
H14A	0.3823	0.8960	0.0132	0.117*
H14B	0.4686	0.7289	0.0448	0.117*
H14C	0.4172	0.9125	0.0740	0.117*

	U11	U22	U33	U12	U13	U23
Cl1	0.0655 (5)	0.1158 (7)	0.0829 (5)	−0.0260 (4)	−0.0364 (4)	0.0270 (4)
S1	0.0599 (4)	0.0634 (4)	0.0533 (4)	0.0146 (3)	−0.0178 (3)	−0.0192 (3)
O1	0.0578 (10)	0.0846 (13)	0.0529 (10)	0.0209 (9)	−0.0111 (8)	−0.0216 (9)
N1	0.0472 (10)	0.0533 (11)	0.0462 (10)	0.0133 (8)	−0.0145 (8)	−0.0115 (8)
N2	0.0474 (10)	0.0602 (12)	0.0416 (10)	0.0094 (9)	−0.0065 (8)	−0.0091 (8)
N3	0.0439 (11)	0.0756 (14)	0.0614 (12)	0.0035 (10)	0.0013 (9)	0.0011 (10)
C2	0.0529 (13)	0.0471 (13)	0.0443 (12)	−0.0004 (10)	−0.0076 (10)	−0.0045 (9)
C3	0.0443 (13)	0.0532 (14)	0.0629 (15)	−0.0014 (10)	−0.0043 (11)	0.0023 (11)
C4	0.0547 (14)	0.0499 (14)	0.0579 (14)	−0.0154 (11)	−0.0227 (12)	0.0120 (11)
C5	0.0666 (16)	0.0654 (16)	0.0411 (12)	−0.0146 (13)	−0.0087 (11)	0.0011 (11)
C6	0.0521 (13)	0.0615 (15)	0.0467 (13)	−0.0054 (11)	−0.0057 (10)	−0.0036 (11)
C1	0.0483 (12)	0.0382 (11)	0.0408 (11)	−0.0016 (9)	−0.0078 (9)	−0.0026 (9)
C7	0.0478 (12)	0.0487 (13)	0.0423 (12)	0.0026 (10)	−0.0046 (10)	−0.0046 (10)
C8	0.0431 (12)	0.0467 (12)	0.0429 (11)	0.0010 (9)	−0.0068 (9)	−0.0021 (9)
C9	0.0426 (12)	0.0454 (12)	0.0422 (11)	0.0077 (9)	−0.0047 (9)	−0.0048 (9)
C10	0.0441 (14)	0.092 (2)	0.090 (2)	0.0071 (14)	−0.0097 (14)	−0.0119 (18)
C11	0.074 (2)	0.083 (2)	0.0737 (19)	0.0307 (16)	−0.0323 (15)	−0.0139 (16)
C12	0.096 (2)	0.0565 (16)	0.0528 (15)	0.0230 (15)	−0.0098 (14)	0.0027 (12)
C13	0.0644 (15)	0.0406 (12)	0.0471 (12)	0.0067 (11)	0.0003 (11)	−0.0024 (10)
C14	0.088 (2)	0.0666 (18)	0.0811 (19)	−0.0112 (15)	0.0187 (16)	0.0070 (15)

Cl1—C4	1.738 (2)	C5—C6	1.372 (3)
S1—C8	1.654 (2)	C5—H5A	0.9300
O1—C7	1.218 (3)	C6—C1	1.390 (3)
N1—C7	1.373 (3)	C6—H6A	0.9300
N1—C8	1.394 (2)	C1—C7	1.487 (3)
N1—H1A	0.8600	C9—C13	1.382 (3)
N2—C8	1.328 (3)	C10—C11	1.354 (4)
N2—C9	1.434 (3)	C10—H10A	0.9300
N2—H2A	0.8600	C11—C12	1.363 (4)
N3—C9	1.320 (3)	C11—H11A	0.9300
N3—C10	1.337 (3)	C12—C13	1.382 (3)
C2—C3	1.385 (3)	C12—H12A	0.9300
C2—C1	1.383 (3)	C13—C14	1.498 (4)
C2—H2B	0.9300	C14—H14A	0.9600
C3—C4	1.377 (3)	C14—H14B	0.9600
C3—H3A	0.9300	C14—H14C	0.9600
C4—C5	1.372 (4)
C7—N1—C8	128.59 (18)	O1—C7—C1	122.05 (18)
C7—N1—H1A	115.7	N1—C7—C1	115.77 (19)
C8—N1—H1A	115.7	N2—C8—N1	116.12 (18)
C8—N2—C9	122.93 (17)	N2—C8—S1	125.52 (16)
C8—N2—H2A	118.5	N1—C8—S1	118.34 (15)
C9—N2—H2A	118.5	N3—C9—C13	125.6 (2)
C9—N3—C10	116.1 (2)	N3—C9—N2	114.81 (19)
C3—C2—C1	120.5 (2)	C13—C9—N2	119.6 (2)
C3—C2—H2B	119.7	N3—C10—C11	123.9 (3)
C1—C2—H2B	119.7	N3—C10—H10A	118.1
C4—C3—C2	118.7 (2)	C11—C10—H10A	118.1
C4—C3—H3A	120.6	C10—C11—C12	118.3 (3)
C2—C3—H3A	120.6	C10—C11—H11A	120.9
C3—C4—C5	121.7 (2)	C12—C11—H11A	120.9
C3—C4—Cl1	119.1 (2)	C11—C12—C13	120.8 (2)
C5—C4—Cl1	119.12 (19)	C11—C12—H12A	119.6
C6—C5—C4	119.2 (2)	C13—C12—H12A	119.6
C6—C5—H5A	120.4	C9—C13—C12	115.3 (2)
C4—C5—H5A	120.4	C9—C13—C14	122.8 (2)
C5—C6—C1	120.6 (2)	C12—C13—C14	121.9 (2)
C5—C6—H6A	119.7	C13—C14—H14A	109.5
C1—C6—H6A	119.7	C13—C14—H14B	109.5
C6—C1—C2	119.2 (2)	H14A—C14—H14B	109.5
C6—C1—C7	117.6 (2)	C13—C14—H14C	109.5
C2—C1—C7	123.05 (19)	H14A—C14—H14C	109.5
O1—C7—N1	122.2 (2)	H14B—C14—H14C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.98	2.655 (2)	135
C2—H2B···N3i	0.93	2.59	3.417 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.98	2.655 (2)	135
C2—H2B⋯N3i	0.93	2.59	3.417 (3)	148

Symmetry code: (i) .