N-(2-Chloro-benzo-yl)-N'-(3-pyrid-yl)thio-urea.

In the mol-ecule of the title compound, C(13)H(10)ClN(3)OS, the dihedral angles between the plane through the thio-urea group and the pyridine and benzene rings are 53.08 (3) and 87.12 (3)°, respectively. The mol-ecules are linked by inter-molecular N-H⋯N hydrogen-bonding inter-actions to form a supra-molecular chain structure along the a axis. An intra-mol-ecular N-H⋯O hydrogen bond is also present.

Related literature

For related literature, see: Campo et al. (2002 ▶); Dong et al. (2006 ▶, 2008 ▶); Foss et al. (2004 ▶); Guillon et al. (1996 ▶); Koch (2001 ▶); Krepps et al. (2001 ▶); Su et al. (2004 ▶, 2006 ▶); Teoh et al. (1999 ▶); Venkatachalam et al. (2004 ▶); West et al. (2000 ▶); Xian et al. (2004 ▶).

Experimental

Crystal data

C13H10ClN3OS

M = 291.75

Triclinic,

a = 8.421 (3) Å

b = 9.282 (4) Å

c = 10.512 (4) Å

α = 98.336 (4)°

β = 110.797 (4)°

γ = 112.532 (4)°

V = 670.9 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.43 mm−1

T = 298 (2) K

0.32 × 0.11 × 0.07 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.874, T max = 0.972

3504 measured reflections

2319 independent reflections

1734 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.02

2319 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019922/rz2227sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019922/rz2227Isup2.hkl

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

C13H10ClN3OS	Z = 2
Mr = 291.75	F000 = 300
Triclinic, P1	Dx = 1.444 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.421 (3) Å	Cell parameters from 1514 reflections
b = 9.282 (4) Å	θ = 2.5–26.6º
c = 10.512 (4) Å	µ = 0.43 mm−1
α = 98.336 (4)º	T = 298 (2) K
β = 110.797 (4)º	Needle, colourless
γ = 112.532 (4)º	0.32 × 0.11 × 0.07 mm
V = 670.9 (5) Å3

Bruker SMART 1000 CCD area-detector diffractometer	2319 independent reflections
Radiation source: fine-focus sealed tube	1734 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.874, Tmax = 0.972	k = −11→9
3504 measured reflections	l = −12→9

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-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.044P)2 + 0.2146P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2319 reflections	Δρmax = 0.20 e Å−3
172 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.41414 (14)	0.64074 (11)	0.50918 (8)	0.0781 (3)
N1	0.4306 (3)	0.5361 (2)	0.1841 (2)	0.0397 (5)
H1	0.3077	0.4966	0.1477	0.048*
N2	0.6871 (3)	0.4903 (2)	0.2029 (2)	0.0416 (5)
H2	0.7561	0.5927	0.2548	0.050*
N3	1.0366 (3)	0.3871 (2)	0.1394 (2)	0.0481 (5)
O1	0.7112 (3)	0.7734 (2)	0.3311 (2)	0.0630 (5)
S1	0.33789 (9)	0.24252 (8)	0.02568 (7)	0.0500 (2)
C1	0.4967 (3)	0.4294 (3)	0.1432 (2)	0.0370 (5)
C2	0.5364 (4)	0.6956 (3)	0.2748 (3)	0.0422 (6)
C3	0.4139 (3)	0.7708 (3)	0.2962 (2)	0.0400 (5)
C4	0.3540 (4)	0.7557 (3)	0.4027 (3)	0.0476 (6)
C5	0.2449 (4)	0.8281 (3)	0.4233 (3)	0.0560 (7)
H5	0.2062	0.8177	0.4955	0.067*
C6	0.1944 (4)	0.9154 (3)	0.3359 (3)	0.0613 (8)
H6	0.1211	0.9644	0.3490	0.074*
C7	0.2513 (4)	0.9307 (3)	0.2296 (3)	0.0593 (7)
H7	0.2157	0.9895	0.1705	0.071*
C8	0.3611 (4)	0.8595 (3)	0.2093 (3)	0.0495 (6)
H8	0.3997	0.8711	0.1371	0.059*
C9	0.9299 (3)	0.4610 (3)	0.1477 (2)	0.0411 (6)
H9	0.9551	0.5586	0.1259	0.049*
C10	0.7848 (3)	0.3985 (3)	0.1872 (2)	0.0380 (5)
C11	0.7442 (4)	0.2524 (3)	0.2178 (3)	0.0481 (6)
H11	0.6456	0.2070	0.2436	0.058*
C12	0.8523 (4)	0.1757 (3)	0.2093 (3)	0.0542 (7)
H12	0.8291	0.0776	0.2300	0.065*
C13	0.9953 (4)	0.2463 (3)	0.1697 (3)	0.0537 (7)
H13	1.0674	0.1930	0.1636	0.064*

	U11	U22	U33	U12	U13	U23
Cl1	0.1271 (8)	0.0975 (6)	0.0704 (5)	0.0861 (6)	0.0617 (5)	0.0496 (5)
N1	0.0341 (10)	0.0395 (11)	0.0488 (11)	0.0192 (9)	0.0225 (9)	0.0076 (9)
N2	0.0372 (11)	0.0368 (10)	0.0569 (12)	0.0195 (9)	0.0271 (10)	0.0101 (9)
N3	0.0439 (12)	0.0496 (12)	0.0650 (14)	0.0268 (10)	0.0339 (11)	0.0184 (11)
O1	0.0406 (11)	0.0539 (11)	0.0758 (13)	0.0192 (9)	0.0209 (10)	−0.0069 (10)
S1	0.0487 (4)	0.0416 (4)	0.0571 (4)	0.0206 (3)	0.0259 (3)	0.0051 (3)
C1	0.0437 (14)	0.0408 (13)	0.0405 (13)	0.0244 (11)	0.0273 (11)	0.0160 (10)
C2	0.0426 (15)	0.0419 (13)	0.0447 (14)	0.0219 (12)	0.0227 (12)	0.0074 (11)
C3	0.0408 (13)	0.0356 (12)	0.0459 (14)	0.0206 (11)	0.0213 (11)	0.0071 (11)
C4	0.0624 (17)	0.0491 (14)	0.0487 (14)	0.0376 (13)	0.0297 (13)	0.0177 (12)
C5	0.0712 (19)	0.0653 (17)	0.0544 (16)	0.0448 (16)	0.0386 (15)	0.0170 (14)
C6	0.0686 (19)	0.0596 (17)	0.0696 (19)	0.0464 (16)	0.0307 (16)	0.0129 (15)
C7	0.0712 (19)	0.0516 (16)	0.0672 (18)	0.0404 (15)	0.0291 (16)	0.0236 (14)
C8	0.0577 (16)	0.0438 (14)	0.0540 (15)	0.0264 (13)	0.0293 (13)	0.0168 (12)
C9	0.0374 (13)	0.0396 (13)	0.0515 (14)	0.0198 (11)	0.0238 (12)	0.0142 (11)
C10	0.0388 (13)	0.0410 (13)	0.0432 (13)	0.0231 (11)	0.0236 (11)	0.0120 (10)
C11	0.0507 (15)	0.0512 (15)	0.0599 (16)	0.0269 (13)	0.0380 (13)	0.0222 (13)
C12	0.0630 (17)	0.0487 (15)	0.0750 (18)	0.0351 (14)	0.0422 (15)	0.0300 (14)
C13	0.0556 (16)	0.0537 (16)	0.0732 (18)	0.0373 (14)	0.0378 (15)	0.0220 (14)

Cl1—C4	1.734 (2)	C5—C6	1.372 (4)
N1—C2	1.368 (3)	C5—H5	0.9300
N1—C1	1.394 (3)	C6—C7	1.369 (4)
N1—H1	0.8600	C6—H6	0.9300
N2—C1	1.331 (3)	C7—C8	1.380 (4)
N2—C10	1.422 (3)	C7—H7	0.9300
N2—H2	0.8600	C8—H8	0.9300
N3—C13	1.335 (3)	C9—C10	1.375 (3)
N3—C9	1.340 (3)	C9—H9	0.9300
O1—C2	1.217 (3)	C10—C11	1.381 (3)
S1—C1	1.659 (2)	C11—C12	1.371 (3)
C2—C3	1.508 (3)	C11—H11	0.9300
C3—C4	1.385 (3)	C12—C13	1.373 (3)
C3—C8	1.386 (3)	C12—H12	0.9300
C4—C5	1.384 (3)	C13—H13	0.9300
C2—N1—C1	128.3 (2)	C7—C6—H6	119.8
C2—N1—H1	115.9	C5—C6—H6	119.8
C1—N1—H1	115.9	C6—C7—C8	120.5 (2)
C1—N2—C10	124.83 (19)	C6—C7—H7	119.7
C1—N2—H2	117.6	C8—C7—H7	119.7
C10—N2—H2	117.6	C7—C8—C3	120.1 (2)
C13—N3—C9	117.2 (2)	C7—C8—H8	119.9
N2—C1—N1	115.4 (2)	C3—C8—H8	119.9
N2—C1—S1	125.54 (17)	N3—C9—C10	122.6 (2)
N1—C1—S1	119.02 (17)	N3—C9—H9	118.7
O1—C2—N1	124.8 (2)	C10—C9—H9	118.7
O1—C2—C3	122.1 (2)	C9—C10—C11	119.2 (2)
N1—C2—C3	113.1 (2)	C9—C10—N2	119.10 (19)
C4—C3—C8	118.6 (2)	C11—C10—N2	121.6 (2)
C4—C3—C2	121.6 (2)	C12—C11—C10	118.6 (2)
C8—C3—C2	119.8 (2)	C12—C11—H11	120.7
C5—C4—C3	121.1 (2)	C10—C11—H11	120.7
C5—C4—Cl1	119.9 (2)	C11—C12—C13	118.8 (2)
C3—C4—Cl1	118.97 (18)	C11—C12—H12	120.6
C6—C5—C4	119.2 (2)	C13—C12—H12	120.6
C6—C5—H5	120.4	N3—C13—C12	123.6 (2)
C4—C5—H5	120.4	N3—C13—H13	118.2
C7—C6—C5	120.4 (2)	C12—C13—H13	118.2
C10—N2—C1—N1	173.77 (19)	C4—C5—C6—C7	0.0 (4)
C10—N2—C1—S1	−7.1 (3)	C5—C6—C7—C8	−0.4 (4)
C2—N1—C1—N2	1.6 (3)	C6—C7—C8—C3	0.4 (4)
C2—N1—C1—S1	−177.58 (18)	C4—C3—C8—C7	0.0 (4)
C1—N1—C2—O1	3.2 (4)	C2—C3—C8—C7	−179.1 (2)
C1—N1—C2—C3	−178.6 (2)	C13—N3—C9—C10	0.8 (4)
O1—C2—C3—C4	−93.6 (3)	N3—C9—C10—C11	−1.0 (4)
N1—C2—C3—C4	88.1 (3)	N3—C9—C10—N2	175.7 (2)
O1—C2—C3—C8	85.4 (3)	C1—N2—C10—C9	129.9 (2)
N1—C2—C3—C8	−92.8 (3)	C1—N2—C10—C11	−53.4 (3)
C8—C3—C4—C5	−0.4 (4)	C9—C10—C11—C12	0.8 (4)
C2—C3—C4—C5	178.7 (2)	N2—C10—C11—C12	−175.8 (2)
C8—C3—C4—Cl1	178.40 (18)	C10—C11—C12—C13	−0.5 (4)
C2—C3—C4—Cl1	−2.5 (3)	C9—N3—C13—C12	−0.5 (4)
C3—C4—C5—C6	0.4 (4)	C11—C12—C13—N3	0.4 (4)
Cl1—C4—C5—C6	−178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.98	2.671 (3)	137
N1—H1···N3i	0.86	2.08	2.886 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.98	2.671 (3)	137
N1—H1⋯N3i	0.86	2.08	2.886 (4)	157

Symmetry code: (i) .