N-Benzoyl-N'-(2-chloro-3-pyrid-yl)thio-urea.

The title compound, C(13)H(10)ClN(3)OS, was prepared by the reaction of 3-amino-2-chloropyridine with benzoyl isothio-cyanate at room temperature. The thio-urea group makes dihedral angles of 47.17 (5) and 51.88 (4)°, respectively, with the benzene and pyridyl rings, while the angle between the benzene and pyridine rings is 8.91 (3)°. Inter-molecular hydrogen-bond inter-actions link neighbouring mol-ecules into an infinite supra-molecular structure.

Related literature

For the biological activities of benzanilide and its N-substituted derivatives, see: Teoh et al. (1999 ▶); Campo et al. (2002 ▶). For the functions of related chloro­phenyl compounds, see: Saeed et al. (2008 ▶); Gowda et al. (2008a ▶,b ▶,c ▶). For an isomeric compound, see: Chai et al. (2008 ▶). For our previous work on thio­urea and its derivatives, see: Dong et al. (2006 ▶, 2007 ▶, 2008a ▶,b ▶). For the synthetic procedure, see: Ding et al. (2008 ▶).

Experimental

Crystal data

C13H10ClN3OS

M = 291.73

Monoclinic,

a = 3.9443 (4) Å

b = 14.9250 (15) Å

c = 22.268 (2) Å

β = 93.889 (1)°

V = 1307.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 298 K

0.41 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.839, T max = 0.924

6459 measured reflections

2315 independent reflections

1661 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.088

S = 1.03

2315 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.21 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/S1600536809027081/at2841sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027081/at2841Isup2.hkl

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

C13H10ClN3OS	F(000) = 600
Mr = 291.73	Dx = 1.482 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2087 reflections
a = 3.9443 (4) Å	θ = 2.3–25.0°
b = 14.9250 (15) Å	µ = 0.45 mm−1
c = 22.268 (2) Å	T = 298 K
β = 93.889 (1)°	Needle-like, colourless
V = 1307.9 (2) Å3	0.41 × 0.20 × 0.18 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2315 independent reflections
Radiation source: fine-focus sealed tube	1661 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
Tmin = 0.839, Tmax = 0.924	k = −17→14
6459 measured reflections	l = −26→24

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0355P)2 + 0.2536P] where P = (Fo2 + 2Fc2)/3
2315 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.21 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
S1	0.45798 (17)	0.45341 (4)	0.58736 (2)	0.0389 (2)
Cl1	0.4376 (2)	0.65386 (5)	0.77102 (3)	0.0581 (2)
N1	0.6989 (5)	0.61464 (12)	0.56704 (8)	0.0351 (5)
H1	0.6662	0.5986	0.5300	0.042*
N2	0.7371 (5)	0.57099 (12)	0.66633 (7)	0.0380 (5)
H2	0.8131	0.6244	0.6727	0.046*
N3	0.5774 (6)	0.49783 (16)	0.81887 (9)	0.0523 (6)
O1	0.8401 (6)	0.73435 (11)	0.62683 (7)	0.0629 (6)
C1	0.6406 (6)	0.54897 (14)	0.60938 (9)	0.0313 (5)
C2	0.8025 (7)	0.70230 (15)	0.57650 (10)	0.0387 (6)
C3	0.8633 (6)	0.75438 (14)	0.52169 (10)	0.0337 (6)
C4	1.0013 (6)	0.71616 (16)	0.47233 (10)	0.0374 (6)
H4	1.0520	0.6553	0.4724	0.045*
C5	1.0642 (7)	0.76769 (17)	0.42297 (11)	0.0475 (7)
H5	1.1643	0.7420	0.3905	0.057*
C6	0.9790 (7)	0.85723 (18)	0.42174 (12)	0.0541 (8)
H6	1.0176	0.8917	0.3881	0.065*
C7	0.8371 (7)	0.89566 (17)	0.47016 (12)	0.0534 (8)
H7	0.7760	0.9558	0.4688	0.064*
C8	0.7846 (7)	0.84549 (16)	0.52092 (11)	0.0459 (7)
H8	0.6974	0.8723	0.5543	0.055*
C9	0.5921 (6)	0.54468 (16)	0.76902 (10)	0.0386 (6)
C10	0.7247 (6)	0.51388 (15)	0.71689 (9)	0.0331 (6)
C11	0.8605 (7)	0.42887 (16)	0.71795 (11)	0.0415 (6)
H11	0.9587	0.4060	0.6844	0.050*
C12	0.8487 (7)	0.37809 (17)	0.76953 (11)	0.0488 (7)
H12	0.9360	0.3202	0.7713	0.059*
C13	0.7047 (8)	0.41517 (19)	0.81819 (12)	0.0547 (8)
H13	0.6955	0.3805	0.8527	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.0473 (4)	0.0371 (4)	0.0322 (3)	−0.0108 (3)	0.0018 (3)	−0.0030 (3)
Cl1	0.0701 (5)	0.0542 (4)	0.0505 (4)	0.0118 (4)	0.0069 (4)	−0.0115 (3)
N1	0.0486 (13)	0.0312 (11)	0.0250 (10)	−0.0073 (10)	−0.0004 (9)	−0.0021 (8)
N2	0.0557 (14)	0.0300 (11)	0.0279 (10)	−0.0078 (10)	−0.0009 (9)	−0.0024 (8)
N3	0.0615 (17)	0.0609 (16)	0.0348 (12)	−0.0110 (13)	0.0049 (11)	0.0027 (11)
O1	0.1150 (19)	0.0399 (10)	0.0337 (10)	−0.0175 (11)	0.0031 (10)	−0.0068 (8)
C1	0.0322 (14)	0.0317 (12)	0.0301 (12)	0.0023 (11)	0.0040 (10)	−0.0022 (10)
C2	0.0478 (17)	0.0328 (14)	0.0352 (14)	−0.0048 (12)	0.0005 (12)	−0.0013 (11)
C3	0.0360 (15)	0.0304 (13)	0.0339 (13)	−0.0053 (11)	−0.0040 (11)	−0.0005 (10)
C4	0.0382 (15)	0.0346 (13)	0.0387 (14)	−0.0050 (11)	−0.0031 (12)	−0.0006 (11)
C5	0.0510 (18)	0.0526 (17)	0.0391 (14)	−0.0094 (14)	0.0046 (13)	−0.0014 (12)
C6	0.065 (2)	0.0529 (18)	0.0436 (16)	−0.0102 (15)	−0.0023 (14)	0.0158 (13)
C7	0.062 (2)	0.0355 (15)	0.0610 (19)	−0.0001 (14)	−0.0046 (16)	0.0089 (13)
C8	0.0536 (18)	0.0362 (15)	0.0479 (15)	0.0007 (13)	0.0037 (13)	−0.0032 (12)
C9	0.0424 (16)	0.0402 (14)	0.0331 (13)	−0.0059 (12)	0.0014 (11)	−0.0041 (11)
C10	0.0360 (15)	0.0332 (13)	0.0294 (12)	−0.0059 (11)	−0.0029 (10)	0.0006 (10)
C11	0.0479 (17)	0.0374 (14)	0.0386 (14)	−0.0008 (12)	−0.0017 (12)	−0.0028 (11)
C12	0.0556 (19)	0.0400 (15)	0.0492 (16)	−0.0053 (14)	−0.0078 (14)	0.0067 (13)
C13	0.067 (2)	0.0562 (18)	0.0398 (16)	−0.0159 (16)	−0.0051 (14)	0.0147 (14)

S1—C1	1.657 (2)	C4—H4	0.9300
Cl1—C9	1.741 (2)	C5—C6	1.378 (3)
N1—C2	1.382 (3)	C5—H5	0.9300
N1—C1	1.390 (3)	C6—C7	1.374 (4)
N1—H1	0.8600	C6—H6	0.9300
N2—C1	1.340 (3)	C7—C8	1.383 (3)
N2—C10	1.416 (3)	C7—H7	0.9300
N2—H2	0.8600	C8—H8	0.9300
N3—C9	1.316 (3)	C9—C10	1.384 (3)
N3—C13	1.332 (3)	C10—C11	1.377 (3)
O1—C2	1.218 (3)	C11—C12	1.379 (3)
C2—C3	1.480 (3)	C11—H11	0.9300
C3—C4	1.382 (3)	C12—C13	1.373 (4)
C3—C8	1.395 (3)	C12—H12	0.9300
C4—C5	1.378 (3)	C13—H13	0.9300
C2—N1—C1	128.66 (18)	C7—C6—H6	120.0
C2—N1—H1	115.7	C5—C6—H6	120.0
C1—N1—H1	115.7	C6—C7—C8	120.5 (2)
C1—N2—C10	125.59 (19)	C6—C7—H7	119.8
C1—N2—H2	117.2	C8—C7—H7	119.8
C10—N2—H2	117.2	C7—C8—C3	119.5 (2)
C9—N3—C13	116.4 (2)	C7—C8—H8	120.3
N2—C1—N1	114.80 (19)	C3—C8—H8	120.3
N2—C1—S1	125.53 (17)	N3—C9—C10	124.9 (2)
N1—C1—S1	119.66 (15)	N3—C9—Cl1	116.11 (19)
O1—C2—N1	121.9 (2)	C10—C9—Cl1	119.02 (18)
O1—C2—C3	122.4 (2)	C11—C10—C9	117.4 (2)
N1—C2—C3	115.72 (19)	C11—C10—N2	122.3 (2)
C4—C3—C8	119.5 (2)	C9—C10—N2	120.2 (2)
C4—C3—C2	122.2 (2)	C10—C11—C12	119.0 (2)
C8—C3—C2	118.3 (2)	C10—C11—H11	120.5
C5—C4—C3	120.4 (2)	C12—C11—H11	120.5
C5—C4—H4	119.8	C13—C12—C11	118.3 (2)
C3—C4—H4	119.8	C13—C12—H12	120.8
C6—C5—C4	120.0 (2)	C11—C12—H12	120.8
C6—C5—H5	120.0	N3—C13—C12	123.9 (2)
C4—C5—H5	120.0	N3—C13—H13	118.0
C7—C6—C5	120.1 (2)	C12—C13—H13	118.0
C10—N2—C1—N1	−175.8 (2)	C4—C3—C8—C7	1.8 (4)
C10—N2—C1—S1	5.3 (3)	C2—C3—C8—C7	−179.7 (2)
C2—N1—C1—N2	−8.8 (4)	C13—N3—C9—C10	0.8 (4)
C2—N1—C1—S1	170.2 (2)	C13—N3—C9—Cl1	−178.04 (19)
C1—N1—C2—O1	−3.9 (4)	N3—C9—C10—C11	−2.1 (4)
C1—N1—C2—C3	176.3 (2)	Cl1—C9—C10—C11	176.72 (18)
O1—C2—C3—C4	144.0 (3)	N3—C9—C10—N2	−178.1 (2)
N1—C2—C3—C4	−36.2 (3)	Cl1—C9—C10—N2	0.7 (3)
O1—C2—C3—C8	−34.6 (4)	C1—N2—C10—C11	50.7 (3)
N1—C2—C3—C8	145.3 (2)	C1—N2—C10—C9	−133.5 (2)
C8—C3—C4—C5	0.7 (4)	C9—C10—C11—C12	2.0 (3)
C2—C3—C4—C5	−177.8 (2)	N2—C10—C11—C12	177.9 (2)
C3—C4—C5—C6	−2.2 (4)	C10—C11—C12—C13	−0.8 (4)
C4—C5—C6—C7	1.2 (4)	C9—N3—C13—C12	0.6 (4)
C5—C6—C7—C8	1.2 (4)	C11—C12—C13—N3	−0.6 (4)
C6—C7—C8—C3	−2.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.94	2.633 (2)	137
N1—H1···S1i	0.86	2.74	3.5982 (18)	178
C12—H12···O1ii	0.93	2.70	3.324 (3)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.94	2.633 (2)	137
N1—H1⋯S1i	0.86	2.74	3.5982 (18)	178
C12—H12⋯O1ii	0.93	2.70	3.324 (3)	125

Symmetry codes: (i) ; (ii) .