4-Chloro-N-[N-(6-methyl-2-pyrid-yl)car-bamo-thio-yl]benzamide.

In the title compound, C(14)H(12)ClN(3)OS, the short exocyclic N-C bond lengths indicate resonance in the thiourea part of the mol-ecule. The title compound is stabilized by an intra-molecular N-H⋯N hydrogen bond, which results in the formation of a six-membered ring. In addition, it shows a synperiplanar conformation between the thio-carbonyl group and the pyridine group. Inter-molecular N-H⋯S and C-H⋯O inter-actions are also present.

Related literature

For the synthesis, see: Mansuroğlu et al. (2008 ▶); Arslan et al. (2003a ▶,b ▶); Binzet et al. (2006 ▶). For general background, see: Arslan et al. (2006a ▶,b ▶, 2007 ▶); Kemp et al. (1997 ▶); Koch et al. (1995 ▶); Nencki (1873 ▶); Özpozan et al. (2000 ▶). For related compounds, see: Arslan et al. (2003a ▶, 2006b ▶, 2007 ▶); Dong et al. (2008 ▶); Duque et al. (2008 ▶); Tutughamiarso & Bolte (2007 ▶); Yue et al. (2008 ▶); Yusof et al. (2008a ▶,b ▶); Xian (2008 ▶); Thiam et al. (2008 ▶); Binzet et al. (2006 ▶); Uğur et al. (2006 ▶).

Experimental

Crystal data

C14H12ClN3OS

M = 305.78

Triclinic,

a = 8.255 (3) Å

b = 9.030 (3) Å

c = 9.957 (3) Å

α = 80.810 (7)°

β = 66.552 (7)°

γ = 87.269 (7)°

V = 672.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.44 mm−1

T = 120 (2) K

0.20 × 0.14 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.918, T max = 0.958

3651 measured reflections

2609 independent reflections

1492 reflections with I > 2σ(I)

R int = 0.100

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.266

S = 0.98

2609 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.50 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041123/hg2444sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041123/hg2444Isup2.hkl

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

C14H12ClN3OS	Z = 2
Mr = 305.78	F(000) = 316
Triclinic, P1	Dx = 1.511 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.255 (3) Å	Cell parameters from 716 reflections
b = 9.030 (3) Å	θ = 2.3–26.3°
c = 9.957 (3) Å	µ = 0.44 mm−1
α = 80.810 (7)°	T = 120 K
β = 66.552 (7)°	Prism, yellow
γ = 87.269 (7)°	0.20 × 0.14 × 0.10 mm
V = 672.1 (4) Å3

Bruker SMART CCD area-detector diffractometer	2609 independent reflections
Radiation source: sealed tube	1492 reflections with I > 2σ(I)
graphite	Rint = 0.100
φ and ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.918, Tmax = 0.958	k = −11→5
3651 measured reflections	l = −12→10

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.266	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.1601P)2] where P = (Fo2 + 2Fc2)/3
2609 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.50 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	−0.0760 (2)	−0.08311 (16)	0.24521 (19)	0.0469 (5)
S1	0.4068 (2)	0.83271 (15)	0.20068 (15)	0.0316 (5)
O1	0.2334 (6)	0.5331 (4)	0.3623 (4)	0.0370 (10)
N1	0.2869 (6)	0.6040 (5)	0.1158 (5)	0.0296 (11)
H1B	0.2730	0.5725	0.0418	0.036*
N2	0.4090 (6)	0.8104 (5)	−0.0583 (5)	0.0282 (11)
H2B	0.4462	0.9040	−0.0760	0.034*
N3	0.3162 (6)	0.6306 (5)	−0.1620 (5)	0.0253 (10)
C1	0.0432 (8)	0.2777 (6)	0.3757 (6)	0.0347 (14)
H1A	0.0183	0.3141	0.4662	0.042*
C2	−0.0314 (8)	0.1427 (6)	0.3760 (7)	0.0394 (15)
H2A	−0.1122	0.0888	0.4661	0.047*
C3	0.0122 (8)	0.0878 (6)	0.2450 (6)	0.0322 (13)
C4	0.1259 (8)	0.1664 (6)	0.1110 (6)	0.0365 (15)
H4A	0.1537	0.1280	0.0211	0.044*
C5	0.1987 (7)	0.3030 (6)	0.1107 (6)	0.0264 (12)
H5A	0.2783	0.3572	0.0201	0.032*
C6	0.1558 (7)	0.3597 (5)	0.2407 (6)	0.0258 (12)
C7	0.2278 (7)	0.5061 (6)	0.2497 (6)	0.0272 (12)
C8	0.3644 (6)	0.7438 (5)	0.0850 (6)	0.0208 (11)
C9	0.4067 (7)	0.7576 (6)	−0.1828 (6)	0.0261 (12)
C10	0.5010 (7)	0.8375 (6)	−0.3213 (6)	0.0291 (13)
H10A	0.5701	0.9232	−0.3321	0.035*
C11	0.4925 (8)	0.7902 (6)	−0.4435 (6)	0.0316 (13)
H11A	0.5503	0.8463	−0.5394	0.038*
C12	0.3987 (7)	0.6598 (6)	−0.4245 (6)	0.0287 (13)
H12A	0.3913	0.6251	−0.5071	0.034*
C13	0.3156 (7)	0.5806 (6)	−0.2823 (6)	0.0229 (12)
C14	0.2159 (8)	0.4360 (6)	−0.2553 (7)	0.0322 (13)
H14A	0.2846	0.3515	−0.2327	0.048*
H14B	0.1965	0.4249	−0.3441	0.048*
H14C	0.1018	0.4375	−0.1715	0.048*

	U11	U22	U33	U12	U13	U23
Cl1	0.0577 (11)	0.0250 (8)	0.0548 (11)	−0.0248 (7)	−0.0183 (9)	−0.0001 (7)
S1	0.0473 (10)	0.0223 (7)	0.0274 (8)	−0.0173 (6)	−0.0164 (7)	−0.0004 (6)
O1	0.053 (3)	0.030 (2)	0.029 (2)	−0.0182 (19)	−0.017 (2)	−0.0027 (17)
N1	0.043 (3)	0.023 (2)	0.022 (2)	−0.019 (2)	−0.009 (2)	−0.0055 (19)
N2	0.038 (3)	0.020 (2)	0.027 (2)	−0.0162 (19)	−0.013 (2)	−0.0017 (18)
N3	0.024 (2)	0.022 (2)	0.034 (3)	−0.0071 (18)	−0.015 (2)	−0.0014 (19)
C1	0.059 (4)	0.022 (3)	0.019 (3)	−0.015 (3)	−0.012 (3)	0.004 (2)
C2	0.045 (4)	0.027 (3)	0.034 (3)	−0.022 (3)	−0.003 (3)	0.003 (3)
C3	0.040 (3)	0.022 (3)	0.029 (3)	−0.019 (2)	−0.009 (3)	0.005 (2)
C4	0.064 (4)	0.021 (3)	0.024 (3)	−0.014 (3)	−0.017 (3)	0.001 (2)
C5	0.033 (3)	0.020 (3)	0.026 (3)	−0.013 (2)	−0.015 (2)	0.007 (2)
C6	0.030 (3)	0.017 (3)	0.030 (3)	−0.008 (2)	−0.013 (3)	0.004 (2)
C7	0.035 (3)	0.020 (3)	0.027 (3)	−0.009 (2)	−0.015 (3)	0.002 (2)
C8	0.020 (3)	0.017 (2)	0.029 (3)	0.000 (2)	−0.016 (2)	0.004 (2)
C9	0.043 (3)	0.017 (3)	0.020 (3)	−0.009 (2)	−0.016 (3)	0.004 (2)
C10	0.036 (3)	0.020 (3)	0.032 (3)	−0.013 (2)	−0.015 (3)	0.003 (2)
C11	0.047 (4)	0.020 (3)	0.024 (3)	−0.013 (2)	−0.011 (3)	0.001 (2)
C12	0.036 (3)	0.025 (3)	0.024 (3)	−0.014 (2)	−0.010 (2)	−0.004 (2)
C13	0.027 (3)	0.021 (3)	0.026 (3)	−0.004 (2)	−0.016 (2)	0.001 (2)
C14	0.042 (3)	0.024 (3)	0.038 (3)	−0.011 (2)	−0.022 (3)	−0.006 (2)

Cl1—C3	1.737 (5)	C4—C5	1.396 (7)
S1—C8	1.655 (5)	C4—H4A	0.9500
O1—C7	1.203 (6)	C5—C6	1.376 (7)
N1—C8	1.376 (6)	C5—H5A	0.9500
N1—C7	1.395 (7)	C6—C7	1.504 (7)
N1—H1B	0.8800	C9—C10	1.382 (7)
N2—C8	1.364 (6)	C10—C11	1.379 (7)
N2—C9	1.405 (6)	C10—H10A	0.9500
N2—H2B	0.8800	C11—C12	1.386 (7)
N3—C9	1.341 (6)	C11—H11A	0.9500
N3—C13	1.347 (7)	C12—C13	1.392 (7)
C1—C2	1.391 (7)	C12—H12A	0.9500
C1—C6	1.405 (7)	C13—C14	1.506 (7)
C1—H1A	0.9500	C14—H14A	0.9800
C2—C3	1.375 (8)	C14—H14B	0.9800
C2—H2A	0.9500	C14—H14C	0.9800
C3—C4	1.390 (8)
C8—N1—C7	128.0 (4)	O1—C7—C6	122.3 (5)
C8—N1—H1B	116.0	N1—C7—C6	113.2 (4)
C7—N1—H1B	116.0	N2—C8—N1	113.5 (4)
C8—N2—C9	132.1 (4)	N2—C8—S1	119.5 (4)
C8—N2—H2B	113.9	N1—C8—S1	127.1 (4)
C9—N2—H2B	113.9	N3—C9—C10	123.1 (5)
C9—N3—C13	118.0 (5)	N3—C9—N2	118.5 (5)
C2—C1—C6	119.5 (5)	C10—C9—N2	118.3 (5)
C2—C1—H1A	120.2	C11—C10—C9	118.6 (5)
C6—C1—H1A	120.2	C11—C10—H10A	120.7
C3—C2—C1	119.7 (5)	C9—C10—H10A	120.7
C3—C2—H2A	120.2	C10—C11—C12	119.2 (5)
C1—C2—H2A	120.2	C10—C11—H11A	120.4
C2—C3—C4	121.4 (5)	C12—C11—H11A	120.4
C2—C3—Cl1	119.9 (4)	C11—C12—C13	118.8 (5)
C4—C3—Cl1	118.7 (4)	C11—C12—H12A	120.6
C3—C4—C5	118.8 (5)	C13—C12—H12A	120.6
C3—C4—H4A	120.6	N3—C13—C12	122.1 (5)
C5—C4—H4A	120.6	N3—C13—C14	116.7 (5)
C6—C5—C4	120.5 (5)	C12—C13—C14	121.2 (5)
C6—C5—H5A	119.8	C13—C14—H14A	109.5
C4—C5—H5A	119.8	C13—C14—H14B	109.5
C5—C6—C1	120.1 (5)	H14A—C14—H14B	109.5
C5—C6—C7	123.7 (5)	C13—C14—H14C	109.5
C1—C6—C7	116.2 (5)	H14A—C14—H14C	109.5
O1—C7—N1	124.4 (5)	H14B—C14—H14C	109.5
C6—C1—C2—C3	3.0 (10)	C9—N2—C8—N1	−7.2 (8)
C1—C2—C3—C4	−1.9 (10)	C9—N2—C8—S1	172.4 (5)
C1—C2—C3—Cl1	178.3 (5)	C7—N1—C8—N2	179.3 (5)
C2—C3—C4—C5	0.9 (10)	C7—N1—C8—S1	−0.3 (8)
Cl1—C3—C4—C5	−179.3 (4)	C13—N3—C9—C10	−1.1 (8)
C3—C4—C5—C6	−1.2 (9)	C13—N3—C9—N2	−179.7 (4)
C4—C5—C6—C1	2.3 (9)	C8—N2—C9—N3	14.9 (9)
C4—C5—C6—C7	−179.8 (5)	C8—N2—C9—C10	−163.8 (5)
C2—C1—C6—C5	−3.3 (9)	N3—C9—C10—C11	4.4 (9)
C2—C1—C6—C7	178.7 (5)	N2—C9—C10—C11	−177.0 (5)
C8—N1—C7—O1	1.7 (9)	C9—C10—C11—C12	−3.7 (8)
C8—N1—C7—C6	−177.9 (5)	C10—C11—C12—C13	0.1 (9)
C5—C6—C7—O1	−157.3 (6)	C9—N3—C13—C12	−2.8 (8)
C1—C6—C7—O1	20.7 (8)	C9—N3—C13—C14	178.7 (5)
C5—C6—C7—N1	22.3 (8)	C11—C12—C13—N3	3.3 (8)
C1—C6—C7—N1	−159.7 (5)	C11—C12—C13—C14	−178.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1i	0.95	2.42	3.303 (7)	154
N2—H2B···S1ii	0.88	2.61	3.464 (5)	165
N1—H1B···N3	0.88	1.90	2.651 (7)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1i	0.95	2.42	3.303 (7)	154
N2—H2B⋯S1ii	0.88	2.61	3.464 (5)	165
N1—H1B⋯N3	0.88	1.90	2.651 (7)	142

Symmetry codes: (i) ; (ii) .