N-Butyl-pyridine-4-thio-carboxamide.

In the title mol-ecule, C(10)H(14)N(2)S, the n-butyl chain assumes a trans zigzag conformation. The dihedral angle between the pyridine ring and the thio-amide plane is 23.38 (8)°. The mol-ecules in the crystal structure are linked by an inter-molecular N-H⋯N hydrogen bond.

Related literature

For related literature, see: Allen et al. (1987 ▶); Klimsova et al. (1999 ▶); Ramachandran (2005 ▶); Vannelli et al. (2002 ▶); Desiraju (1989 ▶); Dodge et al. (2006 ▶).

Experimental

Crystal data

C10H14N2S

M = 194.29

Monoclinic,

a = 8.0895 (3) Å

b = 13.5947 (4) Å

c = 10.4936 (3) Å

β = 111.895 (2)°

V = 1070.78 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 (2) K

0.26 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (; Bruker, 2004 ▶) T min = 0.935, T max = 0.949

11437 measured reflections

2182 independent reflections

1744 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.120

S = 1.06

2182 reflections

122 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062125/is2253sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062125/is2253Isup2.hkl

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

C10H14N2S	F000 = 416
Mr = 194.29	Dx = 1.205 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2182 reflections
a = 8.0895 (3) Å	θ = 2.6–26.3º
b = 13.5947 (4) Å	µ = 0.26 mm−1
c = 10.4936 (3) Å	T = 293 (2) K
β = 111.895 (2)º	Block, brown
V = 1070.78 (6) Å3	0.26 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII kappa diffractometer	2182 independent reflections
Radiation source: fine-focus sealed tube	1744 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 293(2) K	θmax = 26.3º
φ and ω scan	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 2004)	h = −9→10
Tmin = 0.935, Tmax = 0.949	k = −15→16
11437 measured reflections	l = −13→12

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.2939P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2182 reflections	Δρmax = 0.37 e Å−3
122 parameters	Δρmin = −0.38 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
H8	0.753 (2)	−0.0813 (14)	0.501 (2)	0.055 (5)*
C2	0.6652 (3)	−0.27758 (12)	0.74847 (18)	0.0533 (4)
H2	0.5953	−0.3302	0.7016	0.064*
C3	0.6682 (2)	−0.19391 (12)	0.67438 (17)	0.0461 (4)
H3	0.6041	−0.1917	0.5802	0.055*
C4	0.7670 (2)	−0.11385 (11)	0.74138 (15)	0.0406 (4)
C5	0.8613 (3)	−0.12389 (14)	0.88113 (18)	0.0561 (5)
H5	0.9304	−0.0721	0.9312	0.067*
C6	0.8525 (3)	−0.21036 (14)	0.94534 (19)	0.0606 (5)
H6	0.9185	−0.2154	1.0390	0.073*
C7	0.7739 (2)	−0.01937 (11)	0.67065 (17)	0.0446 (4)
C9	0.7746 (3)	0.06103 (12)	0.46367 (18)	0.0519 (4)
H9A	0.8954	0.0864	0.5005	0.062*
H9B	0.6965	0.1116	0.4748	0.062*
C10	0.7241 (3)	0.04039 (12)	0.31368 (18)	0.0514 (4)
H10A	0.6022	0.0168	0.2754	0.062*
H10B	0.8008	−0.0107	0.3017	0.062*
C11	0.7414 (3)	0.13253 (14)	0.23755 (19)	0.0590 (5)
H11A	0.6797	0.1862	0.2618	0.071*
H11B	0.8663	0.1503	0.2673	0.071*
C12	0.6671 (4)	0.1204 (2)	0.0840 (2)	0.0914 (8)
H12A	0.6822	0.1806	0.0417	0.137*
H12B	0.5427	0.1046	0.0533	0.137*
H12C	0.7292	0.0683	0.0590	0.137*
N1	0.7559 (2)	−0.28736 (10)	0.88235 (15)	0.0544 (4)
N8	0.7638 (2)	−0.02581 (10)	0.54257 (14)	0.0450 (3)
S1	0.79203 (10)	0.08676 (3)	0.75316 (5)	0.0775 (3)

	U11	U22	U33	U12	U13	U23
C2	0.0742 (12)	0.0386 (9)	0.0445 (10)	−0.0106 (8)	0.0193 (9)	−0.0039 (7)
C3	0.0591 (10)	0.0420 (8)	0.0351 (8)	−0.0019 (7)	0.0152 (7)	−0.0010 (6)
C4	0.0507 (9)	0.0356 (8)	0.0393 (9)	−0.0011 (7)	0.0212 (7)	−0.0016 (6)
C5	0.0744 (13)	0.0482 (10)	0.0396 (9)	−0.0177 (9)	0.0143 (9)	−0.0047 (7)
C6	0.0829 (14)	0.0548 (11)	0.0359 (9)	−0.0104 (9)	0.0126 (9)	0.0045 (8)
C7	0.0563 (10)	0.0371 (8)	0.0420 (9)	−0.0009 (7)	0.0201 (8)	−0.0013 (6)
C9	0.0716 (12)	0.0354 (8)	0.0507 (10)	0.0021 (8)	0.0253 (9)	0.0062 (7)
C10	0.0649 (11)	0.0424 (9)	0.0485 (10)	0.0035 (8)	0.0228 (8)	0.0079 (7)
C11	0.0721 (13)	0.0510 (11)	0.0593 (12)	0.0064 (9)	0.0307 (10)	0.0166 (8)
C12	0.1018 (19)	0.107 (2)	0.0593 (14)	−0.0033 (15)	0.0234 (13)	0.0293 (13)
N1	0.0776 (11)	0.0426 (8)	0.0432 (8)	−0.0073 (7)	0.0227 (8)	0.0025 (6)
N8	0.0662 (9)	0.0316 (7)	0.0405 (7)	0.0033 (6)	0.0235 (7)	0.0021 (6)
S1	0.1429 (6)	0.0376 (3)	0.0602 (4)	−0.0080 (3)	0.0474 (4)	−0.0114 (2)

C2—N1	1.327 (2)	C9—C10	1.498 (2)
C2—C3	1.383 (2)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—C4	1.378 (2)	C10—C11	1.520 (2)
C3—H3	0.9300	C10—H10A	0.9700
C4—C5	1.384 (2)	C10—H10B	0.9700
C4—C7	1.495 (2)	C11—C12	1.504 (3)
C5—C6	1.370 (3)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C6—N1	1.326 (2)	C12—H12A	0.9600
C6—H6	0.9300	C12—H12B	0.9600
C7—N8	1.318 (2)	C12—H12C	0.9600
C7—S1	1.6608 (16)	N8—H8	0.86 (2)
C9—N8	1.463 (2)
N1—C2—C3	123.97 (16)	H9A—C9—H9B	107.8
N1—C2—H2	118.0	C9—C10—C11	110.82 (15)
C3—C2—H2	118.0	C9—C10—H10A	109.5
C4—C3—C2	119.42 (15)	C11—C10—H10A	109.5
C4—C3—H3	120.3	C9—C10—H10B	109.5
C2—C3—H3	120.3	C11—C10—H10B	109.5
C3—C4—C5	116.63 (15)	H10A—C10—H10B	108.1
C3—C4—C7	123.18 (14)	C12—C11—C10	113.24 (19)
C5—C4—C7	120.18 (15)	C12—C11—H11A	108.9
C6—C5—C4	119.76 (16)	C10—C11—H11A	108.9
C6—C5—H5	120.1	C12—C11—H11B	108.9
C4—C5—H5	120.1	C10—C11—H11B	108.9
N1—C6—C5	124.15 (17)	H11A—C11—H11B	107.7
N1—C6—H6	117.9	C11—C12—H12A	109.5
C5—C6—H6	117.9	C11—C12—H12B	109.5
N8—C7—C4	116.70 (13)	H12A—C12—H12B	109.5
N8—C7—S1	123.30 (12)	C11—C12—H12C	109.5
C4—C7—S1	120.00 (12)	H12A—C12—H12C	109.5
N8—C9—C10	113.15 (14)	H12B—C12—H12C	109.5
N8—C9—H9A	108.9	C6—N1—C2	116.05 (15)
C10—C9—H9A	108.9	C7—N8—C9	121.94 (14)
N8—C9—H9B	108.9	C7—N8—H8	122.2 (13)
C10—C9—H9B	108.9	C9—N8—H8	115.8 (13)
N1—C2—C3—C4	−1.5 (3)	C5—C4—C7—S1	−33.5 (2)
C2—C3—C4—C5	1.2 (2)	N8—C9—C10—C11	−178.86 (16)
C2—C3—C4—C7	−178.13 (16)	C9—C10—C11—C12	−171.50 (18)
C3—C4—C5—C6	−0.1 (3)	C5—C6—N1—C2	0.6 (3)
C7—C4—C5—C6	179.24 (18)	C3—C2—N1—C6	0.6 (3)
C4—C5—C6—N1	−0.9 (3)	C4—C7—N8—C9	−178.06 (15)
C3—C4—C7—N8	−33.7 (2)	S1—C7—N8—C9	2.4 (3)
C5—C4—C7—N8	146.99 (17)	C10—C9—N8—C7	−168.50 (16)
C3—C4—C7—S1	145.88 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···N1i	0.859 (19)	2.182 (19)	3.033 (2)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯N1i	0.859 (19)	2.182 (19)	3.033 (2)	171 (2)

Symmetry code: (i) .