N-[(Piperidin-1-yl)carbothioyl]benz-amide.

In the title compound, C(13)H(16)N(2)OS, the piperidine ring exhibit a classical chair conformation. In the crystal, the mol-ecules are linked by N-H⋯O hydrogen bonds, forming zigzag chains running parallel to the c axis.

Related literature

For complexes with the title compound as a ligand, see: Mohamadou et al. (1994 ▶); Salyn et al. (1977 ▶); Röbisch et al. (1982 ▶).

Experimental

Crystal data

C13H16N2OS

M = 248.34

Monoclinic,

a = 10.913 (3) Å

b = 14.297 (4) Å

c = 8.323 (2) Å

β = 102.212 (6)°

V = 1269.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 298 K

0.50 × 0.41 × 0.38 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.889, T max = 0.915

7091 measured reflections

2221 independent reflections

1727 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.126

S = 1.08

2221 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶), PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004170X/bt5376sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004170X/bt5376Isup2.hkl

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

C13H16N2OS	F(000) = 528
Mr = 248.34	Dx = 1.300 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1679 reflections
a = 10.913 (3) Å	θ = 1.9–25.0°
b = 14.297 (4) Å	µ = 0.24 mm−1
c = 8.323 (2) Å	T = 298 K
β = 102.212 (6)°	Needle, colourless
V = 1269.2 (6) Å3	0.50 × 0.41 × 0.38 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2221 independent reflections
Radiation source: fine-focus sealed tube	1727 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scan	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→8
Tmin = 0.889, Tmax = 0.915	k = −16→17
7091 measured reflections	l = −9→9

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0702P)2 + 0.1087P] where P = (Fo2 + 2Fc2)/3
2221 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.27 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	0.93006 (6)	0.86988 (4)	0.12334 (8)	0.0562 (2)
O1	1.15395 (14)	0.65828 (11)	0.05387 (17)	0.0500 (4)
N1	1.07366 (15)	0.72851 (13)	0.2538 (2)	0.0419 (4)
H1A	1.0864	0.7427	0.3564	0.050*
N2	0.88426 (17)	0.68658 (13)	0.0845 (2)	0.0444 (5)
C1	1.2732 (2)	0.63954 (15)	0.4875 (3)	0.0472 (6)
H1B	1.1968	0.6424	0.5201	0.057*
C2	1.3821 (3)	0.61791 (16)	0.6010 (3)	0.0546 (6)
H2A	1.3790	0.6072	0.7102	0.066*
C3	1.4937 (2)	0.61231 (16)	0.5526 (3)	0.0560 (7)
H3A	1.5665	0.5981	0.6294	0.067*
C4	1.4996 (2)	0.62748 (16)	0.3912 (3)	0.0526 (6)
H4A	1.5760	0.6230	0.3590	0.063*
C5	1.3923 (2)	0.64924 (15)	0.2774 (3)	0.0448 (5)
H5A	1.3961	0.6589	0.1681	0.054*
C6	1.27884 (19)	0.65682 (14)	0.3256 (2)	0.0385 (5)
C7	1.1646 (2)	0.68059 (14)	0.1983 (2)	0.0393 (5)
C8	0.95923 (19)	0.75579 (16)	0.1496 (2)	0.0404 (5)
C9	0.9072 (2)	0.58599 (16)	0.1188 (3)	0.0521 (6)
H9A	0.9804	0.5785	0.2071	0.062*
H9B	0.9243	0.5554	0.0218	0.062*
C10	0.7954 (2)	0.53997 (16)	0.1670 (3)	0.0502 (6)
H10A	0.8099	0.4731	0.1782	0.060*
H10B	0.7864	0.5640	0.2729	0.060*
C11	0.6756 (2)	0.55748 (17)	0.0417 (3)	0.0576 (7)
H11A	0.6051	0.5319	0.0813	0.069*
H11B	0.6797	0.5264	−0.0605	0.069*
C12	0.6569 (2)	0.66148 (17)	0.0119 (3)	0.0511 (6)
H12A	0.5826	0.6717	−0.0736	0.061*
H12B	0.6438	0.6914	0.1115	0.061*
C13	0.7685 (2)	0.70500 (17)	−0.0388 (3)	0.0491 (6)
H13A	0.7767	0.6796	−0.1441	0.059*
H13B	0.7559	0.7720	−0.0514	0.059*

	U11	U22	U33	U12	U13	U23
S1	0.0585 (4)	0.0490 (4)	0.0571 (4)	0.0034 (3)	0.0029 (3)	0.0042 (3)
O1	0.0432 (9)	0.0702 (11)	0.0352 (9)	0.0035 (8)	0.0048 (7)	−0.0055 (7)
N1	0.0350 (10)	0.0584 (11)	0.0305 (9)	0.0052 (9)	0.0028 (7)	−0.0008 (7)
N2	0.0314 (10)	0.0495 (11)	0.0489 (10)	0.0030 (9)	0.0009 (8)	0.0062 (8)
C1	0.0428 (13)	0.0551 (14)	0.0431 (13)	0.0013 (11)	0.0078 (10)	0.0043 (10)
C2	0.0624 (16)	0.0561 (15)	0.0399 (13)	0.0032 (13)	−0.0013 (11)	0.0079 (10)
C3	0.0446 (14)	0.0504 (14)	0.0619 (16)	0.0031 (11)	−0.0136 (12)	0.0039 (11)
C4	0.0352 (13)	0.0545 (15)	0.0653 (16)	0.0000 (11)	0.0044 (11)	−0.0026 (11)
C5	0.0383 (12)	0.0496 (13)	0.0456 (12)	−0.0010 (10)	0.0065 (10)	−0.0002 (10)
C6	0.0341 (12)	0.0411 (11)	0.0387 (11)	−0.0015 (9)	0.0042 (9)	0.0004 (9)
C7	0.0342 (12)	0.0475 (12)	0.0359 (11)	−0.0035 (10)	0.0065 (9)	0.0032 (9)
C8	0.0351 (11)	0.0556 (13)	0.0313 (10)	0.0023 (10)	0.0084 (9)	0.0030 (9)
C9	0.0374 (13)	0.0471 (13)	0.0689 (16)	0.0065 (11)	0.0051 (11)	0.0026 (11)
C10	0.0447 (14)	0.0438 (12)	0.0586 (13)	−0.0018 (11)	0.0033 (11)	0.0000 (10)
C11	0.0454 (14)	0.0603 (15)	0.0625 (15)	−0.0081 (12)	0.0012 (12)	−0.0025 (12)
C12	0.0338 (12)	0.0640 (15)	0.0505 (13)	0.0001 (11)	−0.0027 (10)	−0.0025 (11)
C13	0.0396 (13)	0.0599 (14)	0.0420 (12)	0.0039 (11)	−0.0041 (10)	0.0062 (10)

S1—C8	1.667 (2)	C5—C6	1.385 (3)
O1—C7	1.225 (2)	C5—H5A	0.9300
N1—C7	1.364 (3)	C6—C7	1.495 (3)
N1—C8	1.416 (3)	C9—C10	1.514 (3)
N1—H1A	0.8600	C9—H9A	0.9700
N2—C8	1.325 (3)	C9—H9B	0.9700
N2—C13	1.473 (3)	C10—C11	1.511 (3)
N2—C9	1.477 (3)	C10—H10A	0.9700
C1—C6	1.385 (3)	C10—H10B	0.9700
C1—C2	1.388 (3)	C11—C12	1.514 (3)
C1—H1B	0.9300	C11—H11A	0.9700
C2—C3	1.364 (4)	C11—H11B	0.9700
C2—H2A	0.9300	C12—C13	1.506 (3)
C3—C4	1.376 (3)	C12—H12A	0.9700
C3—H3A	0.9300	C12—H12B	0.9700
C4—C5	1.377 (3)	C13—H13A	0.9700
C4—H4A	0.9300	C13—H13B	0.9700
C7—N1—C8	122.74 (17)	N2—C9—C10	111.15 (18)
C7—N1—H1A	118.6	N2—C9—H9A	109.4
C8—N1—H1A	118.6	C10—C9—H9A	109.4
C8—N2—C13	121.05 (18)	N2—C9—H9B	109.4
C8—N2—C9	125.68 (18)	C10—C9—H9B	109.4
C13—N2—C9	113.22 (18)	H9A—C9—H9B	108.0
C6—C1—C2	119.6 (2)	C11—C10—C9	111.9 (2)
C6—C1—H1B	120.2	C11—C10—H10A	109.2
C2—C1—H1B	120.2	C9—C10—H10A	109.2
C3—C2—C1	120.2 (2)	C11—C10—H10B	109.2
C3—C2—H2A	119.9	C9—C10—H10B	109.2
C1—C2—H2A	119.9	H10A—C10—H10B	107.9
C2—C3—C4	120.5 (2)	C10—C11—C12	110.07 (19)
C2—C3—H3A	119.7	C10—C11—H11A	109.6
C4—C3—H3A	119.7	C12—C11—H11A	109.6
C3—C4—C5	119.9 (2)	C10—C11—H11B	109.6
C3—C4—H4A	120.0	C12—C11—H11B	109.6
C5—C4—H4A	120.0	H11A—C11—H11B	108.2
C4—C5—C6	120.1 (2)	C13—C12—C11	111.2 (2)
C4—C5—H5A	120.0	C13—C12—H12A	109.4
C6—C5—H5A	120.0	C11—C12—H12A	109.4
C1—C6—C5	119.7 (2)	C13—C12—H12B	109.4
C1—C6—C7	121.89 (19)	C11—C12—H12B	109.4
C5—C6—C7	118.43 (18)	H12A—C12—H12B	108.0
O1—C7—N1	122.59 (19)	N2—C13—C12	110.88 (18)
O1—C7—C6	121.86 (19)	N2—C13—H13A	109.5
N1—C7—C6	115.56 (17)	C12—C13—H13A	109.5
N2—C8—N1	115.66 (19)	N2—C13—H13B	109.5
N2—C8—S1	126.36 (16)	C12—C13—H13B	109.5
N1—C8—S1	117.96 (16)	H13A—C13—H13B	108.1
C6—C1—C2—C3	−1.0 (3)	C13—N2—C8—N1	−173.80 (17)
C1—C2—C3—C4	−0.3 (4)	C9—N2—C8—N1	3.5 (3)
C2—C3—C4—C5	0.5 (3)	C13—N2—C8—S1	7.6 (3)
C3—C4—C5—C6	0.7 (3)	C9—N2—C8—S1	−175.12 (16)
C2—C1—C6—C5	2.2 (3)	C7—N1—C8—N2	65.2 (3)
C2—C1—C6—C7	−179.9 (2)	C7—N1—C8—S1	−116.00 (19)
C4—C5—C6—C1	−2.0 (3)	C8—N2—C9—C10	128.2 (2)
C4—C5—C6—C7	179.98 (19)	C13—N2—C9—C10	−54.3 (2)
C8—N1—C7—O1	0.5 (3)	N2—C9—C10—C11	53.4 (3)
C8—N1—C7—C6	−179.52 (18)	C9—C10—C11—C12	−54.2 (3)
C1—C6—C7—O1	−148.6 (2)	C10—C11—C12—C13	55.5 (3)
C5—C6—C7—O1	29.4 (3)	C8—N2—C13—C12	−126.5 (2)
C1—C6—C7—N1	31.4 (3)	C9—N2—C13—C12	55.8 (2)
C5—C6—C7—N1	−150.61 (19)	C11—C12—C13—N2	−56.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.18	2.949 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.18	2.949 (2)	149

Symmetry code: (i) .