N-Phenyl-piperidine-1-carbothio-amide.

The title compound, C(12)H(16)N(2)S, was prepared by the reaction of with phenyl isothio-cyanate and piperidine. In the crystal structure, the mol-ecule exhibits inter-molecular N-H⋯S hydrogen bonds and weak intra-molecular C-H⋯S and C-H⋯N hydrogen-bonding inter-actions.

Related literature

For related literature, see: Casas et al. (2002 ▶); Cowley et al. (2002 ▶); Toshiaki et al. (2003 ▶).

Experimental

Crystal data

C12H16N2S

M = 220.33

Monoclinic,

a = 11.661 (2) Å

b = 9.5220 (19) Å

c = 10.989 (2) Å

β = 102.15 (3)°

V = 1192.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 (2) K

0.25 × 0.20 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2681 measured reflections

2547 independent reflections

1972 reflections with I > 2σ(I)

R int = 0.009

3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.123

S = 1.02

2547 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025142/at2604sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025142/at2604Isup2.hkl

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

C12H16N2S	F000 = 472
Mr = 220.33	Dx = 1.227 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.661 (2) Å	θ = 1.8–27.0º
b = 9.5220 (19) Å	µ = 0.24 mm−1
c = 10.989 (2) Å	T = 293 (2) K
β = 102.15 (3)º	Block, colourless
V = 1192.8 (4) Å3	0.25 × 0.20 × 0.18 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.009
Radiation source: fine-focus sealed tube	θmax = 27.0º
Monochromator: graphite	θmin = 1.8º
T = 293(2) K	h = −13→13
ω scans	k = −11→0
Absorption correction: none	l = 0→13
2681 measured reflections	3 standard reflections
2547 independent reflections	every 100 reflections
1972 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0738P)2 + 0.2418P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.26 e Å−3
2547 reflections	Δρmin = −0.38 e Å−3
149 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.129 (8)
Secondary atom site location: difference Fourier map

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	0.48254 (4)	0.19137 (5)	0.42566 (4)	0.04595 (19)
N1	0.33547 (12)	0.37786 (15)	0.29140 (15)	0.0441 (4)
N2	0.53031 (12)	0.41101 (18)	0.29001 (15)	0.0465 (4)
C1	0.23443 (15)	0.2923 (2)	0.3048 (2)	0.0507 (5)
H1A	0.1878	0.3431	0.3537	0.061*
H1B	0.2615	0.2060	0.3484	0.061*
C2	0.15982 (19)	0.2580 (2)	0.1783 (2)	0.0655 (6)
H2B	0.0900	0.2083	0.1890	0.079*
H2C	0.2034	0.1966	0.1341	0.079*
C3	0.1237 (2)	0.3906 (2)	0.1007 (3)	0.0701 (7)
H3A	0.0837	0.3642	0.0173	0.084*
H3B	0.0696	0.4450	0.1377	0.084*
C4	0.23033 (19)	0.4800 (2)	0.09364 (19)	0.0558 (5)
H4A	0.2794	0.4308	0.0465	0.067*
H4B	0.2051	0.5676	0.0512	0.067*
C5	0.29967 (16)	0.51043 (19)	0.22297 (19)	0.0449 (4)
C6	0.44703 (14)	0.33344 (17)	0.33069 (15)	0.0362 (4)
C7	0.65404 (14)	0.39270 (17)	0.32415 (16)	0.0388 (4)
C8	0.71647 (15)	0.38347 (18)	0.23028 (18)	0.0439 (4)
H8A	0.6772	0.3841	0.1473	0.053*
C9	0.83783 (16)	0.3733 (2)	0.2604 (2)	0.0522 (5)
H9A	0.8797	0.3673	0.1973	0.063*
C10	0.89689 (16)	0.3721 (2)	0.3832 (2)	0.0538 (5)
H10A	0.9782	0.3646	0.4030	0.065*
C11	0.83420 (16)	0.3822 (2)	0.4765 (2)	0.0533 (5)
H11A	0.8737	0.3814	0.5594	0.064*
C12	0.71314 (16)	0.3935 (2)	0.44777 (18)	0.0481 (4)
H12A	0.6716	0.4015	0.5110	0.058*
H5A	0.3633 (19)	0.566 (2)	0.220 (2)	0.055 (6)*
H5B	0.2457 (19)	0.561 (2)	0.267 (2)	0.056 (6)*
H2	0.5075 (17)	0.463 (2)	0.230 (2)	0.051 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0424 (3)	0.0424 (3)	0.0520 (3)	0.00420 (18)	0.00770 (19)	0.01026 (19)
N1	0.0343 (7)	0.0404 (8)	0.0576 (9)	−0.0006 (6)	0.0095 (6)	0.0122 (7)
N2	0.0336 (7)	0.0551 (9)	0.0494 (9)	−0.0004 (7)	0.0058 (6)	0.0162 (7)
C1	0.0344 (9)	0.0481 (10)	0.0717 (13)	0.0002 (7)	0.0158 (8)	0.0176 (9)
C2	0.0502 (11)	0.0419 (11)	0.0962 (17)	−0.0057 (9)	−0.0033 (11)	0.0036 (11)
C3	0.0613 (13)	0.0556 (13)	0.0792 (16)	−0.0016 (10)	−0.0179 (11)	0.0042 (11)
C4	0.0655 (12)	0.0503 (11)	0.0525 (11)	0.0128 (9)	0.0142 (9)	0.0097 (9)
C5	0.0370 (8)	0.0355 (9)	0.0631 (12)	0.0021 (7)	0.0124 (8)	0.0092 (8)
C6	0.0351 (8)	0.0369 (8)	0.0367 (8)	−0.0014 (6)	0.0078 (6)	−0.0016 (6)
C7	0.0335 (8)	0.0343 (8)	0.0475 (9)	−0.0029 (6)	0.0059 (7)	0.0017 (7)
C8	0.0418 (9)	0.0420 (10)	0.0474 (10)	−0.0041 (7)	0.0081 (7)	0.0007 (7)
C9	0.0434 (10)	0.0475 (11)	0.0706 (13)	−0.0022 (8)	0.0233 (9)	−0.0035 (9)
C10	0.0320 (9)	0.0451 (10)	0.0814 (14)	−0.0008 (7)	0.0052 (9)	0.0032 (9)
C11	0.0435 (10)	0.0539 (12)	0.0556 (11)	−0.0051 (8)	−0.0054 (8)	0.0008 (9)
C12	0.0428 (9)	0.0536 (11)	0.0466 (10)	−0.0036 (8)	0.0066 (8)	−0.0027 (8)

S1—C6	1.7056 (17)	C4—C5	1.508 (3)
N1—C6	1.349 (2)	C4—H4A	0.9700
N1—C1	1.465 (2)	C4—H4B	0.9700
N1—C5	1.484 (2)	C5—H5A	0.92 (2)
N2—C6	1.368 (2)	C5—H5B	0.99 (2)
N2—C7	1.423 (2)	C7—C8	1.385 (3)
N2—H2	0.82 (2)	C7—C12	1.388 (2)
C1—C2	1.512 (3)	C8—C9	1.387 (3)
C1—H1A	0.9700	C8—H8A	0.9300
C1—H1B	0.9700	C9—C10	1.380 (3)
C2—C3	1.533 (3)	C9—H9A	0.9300
C2—H2B	0.9700	C10—C11	1.383 (3)
C2—H2C	0.9700	C10—H10A	0.9300
C3—C4	1.522 (3)	C11—C12	1.384 (3)
C3—H3A	0.9700	C11—H11A	0.9300
C3—H3B	0.9700	C12—H12A	0.9300
C6—N1—C1	122.35 (14)	H4A—C4—H4B	108.2
C6—N1—C5	125.33 (14)	N1—C5—C4	110.63 (16)
C1—N1—C5	112.18 (14)	N1—C5—H5A	111.5 (13)
C6—N2—C7	126.72 (15)	C4—C5—H5A	110.9 (13)
C6—N2—H2	117.1 (14)	N1—C5—H5B	107.9 (13)
C7—N2—H2	115.0 (14)	C4—C5—H5B	106.3 (12)
N1—C1—C2	110.30 (17)	H5A—C5—H5B	109.3 (18)
N1—C1—H1A	109.6	N1—C6—N2	115.41 (15)
C2—C1—H1A	109.6	N1—C6—S1	122.54 (12)
N1—C1—H1B	109.6	N2—C6—S1	122.05 (12)
C2—C1—H1B	109.6	C8—C7—C12	119.93 (16)
H1A—C1—H1B	108.1	C8—C7—N2	118.31 (16)
C1—C2—C3	111.80 (18)	C12—C7—N2	121.62 (16)
C1—C2—H2B	109.3	C7—C8—C9	119.78 (18)
C3—C2—H2B	109.3	C7—C8—H8A	120.1
C1—C2—H2C	109.3	C9—C8—H8A	120.1
C3—C2—H2C	109.3	C10—C9—C8	120.50 (19)
H2B—C2—H2C	107.9	C10—C9—H9A	119.7
C4—C3—C2	110.95 (18)	C8—C9—H9A	119.7
C4—C3—H3A	109.4	C9—C10—C11	119.48 (17)
C2—C3—H3A	109.4	C9—C10—H10A	120.3
C4—C3—H3B	109.4	C11—C10—H10A	120.3
C2—C3—H3B	109.4	C10—C11—C12	120.59 (18)
H3A—C3—H3B	108.0	C10—C11—H11A	119.7
C5—C4—C3	109.95 (18)	C12—C11—H11A	119.7
C5—C4—H4A	109.7	C11—C12—C7	119.70 (18)
C3—C4—H4A	109.7	C11—C12—H12A	120.1
C5—C4—H4B	109.7	C7—C12—H12A	120.1
C3—C4—H4B	109.7
C6—N1—C1—C2	−117.8 (2)	C7—N2—C6—N1	175.49 (17)
C5—N1—C1—C2	58.1 (2)	C7—N2—C6—S1	−3.9 (3)
N1—C1—C2—C3	−54.1 (2)	C6—N2—C7—C8	129.22 (19)
C1—C2—C3—C4	52.7 (3)	C6—N2—C7—C12	−55.1 (3)
C2—C3—C4—C5	−53.8 (3)	C12—C7—C8—C9	0.8 (3)
C6—N1—C5—C4	115.4 (2)	N2—C7—C8—C9	176.49 (16)
C1—N1—C5—C4	−60.4 (2)	C7—C8—C9—C10	0.1 (3)
C3—C4—C5—N1	57.2 (2)	C8—C9—C10—C11	−0.5 (3)
C1—N1—C6—N2	167.41 (17)	C9—C10—C11—C12	0.0 (3)
C5—N1—C6—N2	−8.0 (3)	C10—C11—C12—C7	0.9 (3)
C1—N1—C6—S1	−13.2 (2)	C8—C7—C12—C11	−1.3 (3)
C5—N1—C6—S1	171.48 (14)	N2—C7—C12—C11	−176.82 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.82 (2)	2.78 (2)	3.5520 (19)	156.1 (18)
C1—H1B···S1	0.97	2.54	3.073 (2)	114
C5—H5A···N2	0.92 (2)	2.44 (2)	2.800 (2)	103.8 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.82 (2)	2.78 (2)	3.5520 (19)	156.1 (18)
C1—H1B⋯S1	0.97	2.54	3.073 (2)	114
C5—H5A⋯N2	0.92 (2)	2.44 (2)	2.800 (2)	103.8 (14)

Symmetry code: (i) .