N-Phenyl-pyrrolidine-1-carbothio-amide.

The title compound, C(11)H(14)N(2)S, was prepared by the reaction of 1-isothio-cyanato-benzene and pyrrolidine. In the crystal structure, inter-molecular N-H⋯S inter-actions are present.

Related literature

For the applications of thio­amides, see: Toshiaki et al. (2003 ▶). For related structures, see: Casas et al. (2002 ▶); Cowley et al. (2002 ▶);

Experimental

Crystal data

C11H14N2S

M = 206.30

Monoclinic,

a = 11.195 (2) Å

b = 8.5694 (17) Å

c = 11.414 (2) Å

β = 108.03 (3)°

V = 1041.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 (2) K

0.25 × 0.20 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

4554 measured reflections

2393 independent reflections

2214 reflections with I > 2σ(I)

R int = 0.018

3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.119

S = 1.30

2393 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.46 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/S1600536808040907/at2689sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040907/at2689Isup2.hkl

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

C11H14N2S	F(000) = 440
Mr = 206.30	Dx = 1.316 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.195 (2) Å	θ = 1.8–27.0°
b = 8.5694 (17) Å	µ = 0.27 mm−1
c = 11.414 (2) Å	T = 293 K
β = 108.03 (3)°	Block, colourless
V = 1041.2 (4) Å3	0.25 × 0.20 × 0.18 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.018
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 1.9°
graphite	h = −14→14
ω scans	k = −11→11
4554 measured reflections	l = −14→14
2393 independent reflections	3 standard reflections every 100 reflections
2214 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.30	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.3194P] where P = (Fo2 + 2Fc2)/3
2393 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.46 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	0.50030 (4)	0.12695 (5)	0.27663 (4)	0.01992 (15)
N2	0.34546 (13)	0.29432 (17)	0.09833 (13)	0.0162 (3)
N1	0.53176 (13)	0.23342 (19)	0.06683 (13)	0.0183 (3)
H1A	0.4979	0.2678	−0.0068	0.022*
C7	0.45718 (15)	0.2256 (2)	0.14190 (15)	0.0152 (3)
C5	0.66016 (16)	0.1894 (2)	0.10058 (16)	0.0177 (4)
C8	0.30485 (17)	0.3898 (2)	−0.01429 (16)	0.0200 (4)
H8A	0.2822	0.3248	−0.0874	0.024*
H8B	0.3704	0.4617	−0.0182	0.024*
C11	0.25255 (16)	0.2964 (2)	0.16519 (16)	0.0203 (4)
H11A	0.2806	0.3614	0.2382	0.024*
H11B	0.2364	0.1919	0.1892	0.024*
C4	0.70097 (18)	0.0997 (2)	0.01900 (18)	0.0225 (4)
H4A	0.6439	0.0646	−0.0541	0.027*
C9	0.19114 (17)	0.4771 (2)	−0.00189 (18)	0.0245 (4)
H9A	0.1312	0.4984	−0.0821	0.029*
H9B	0.2158	0.5748	0.0418	0.029*
C6	0.74613 (17)	0.2436 (2)	0.20885 (17)	0.0241 (4)
H6A	0.7196	0.3065	0.2624	0.029*
C2	0.91276 (19)	0.1125 (3)	0.1562 (2)	0.0337 (5)
H2A	0.9971	0.0854	0.1755	0.040*
C3	0.82751 (19)	0.0628 (2)	0.0475 (2)	0.0307 (5)
H3A	0.8551	0.0038	−0.0075	0.037*
C10	0.13624 (17)	0.3649 (2)	0.07178 (18)	0.0243 (4)
H10A	0.0844	0.4197	0.1124	0.029*
H10B	0.0865	0.2841	0.0193	0.029*
C1	0.87165 (18)	0.2032 (3)	0.23648 (19)	0.0309 (5)
H1B	0.9289	0.2375	0.3098	0.037*

	U11	U22	U33	U12	U13	U23
S1	0.0211 (2)	0.0247 (3)	0.0136 (2)	0.00322 (17)	0.00489 (16)	0.00532 (16)
N2	0.0159 (7)	0.0202 (7)	0.0125 (6)	0.0012 (6)	0.0045 (5)	0.0028 (5)
N1	0.0162 (7)	0.0264 (8)	0.0124 (6)	0.0025 (6)	0.0049 (5)	0.0027 (6)
C7	0.0164 (8)	0.0160 (8)	0.0127 (7)	−0.0019 (6)	0.0036 (6)	−0.0021 (6)
C5	0.0180 (8)	0.0180 (8)	0.0175 (8)	0.0006 (7)	0.0060 (7)	0.0036 (6)
C8	0.0204 (8)	0.0248 (9)	0.0150 (8)	0.0033 (7)	0.0056 (6)	0.0049 (7)
C11	0.0174 (8)	0.0270 (10)	0.0181 (8)	−0.0008 (7)	0.0078 (7)	0.0009 (7)
C4	0.0254 (9)	0.0195 (9)	0.0248 (9)	0.0001 (7)	0.0108 (7)	−0.0009 (7)
C9	0.0204 (9)	0.0264 (10)	0.0264 (9)	0.0051 (7)	0.0070 (7)	0.0076 (8)
C6	0.0223 (9)	0.0304 (10)	0.0192 (9)	−0.0014 (8)	0.0057 (7)	0.0016 (7)
C2	0.0200 (9)	0.0385 (12)	0.0436 (12)	0.0075 (8)	0.0111 (9)	0.0164 (10)
C3	0.0298 (10)	0.0266 (10)	0.0423 (12)	0.0080 (8)	0.0206 (9)	0.0029 (9)
C10	0.0176 (8)	0.0299 (10)	0.0262 (9)	0.0017 (7)	0.0078 (7)	0.0028 (8)
C1	0.0201 (9)	0.0415 (12)	0.0264 (10)	−0.0039 (8)	0.0002 (8)	0.0098 (9)

S1—C7	1.6892 (17)	C4—C3	1.388 (3)
N2—C7	1.332 (2)	C4—H4A	0.9300
N2—C11	1.468 (2)	C9—C10	1.527 (3)
N2—C8	1.472 (2)	C9—H9A	0.9700
N1—C7	1.371 (2)	C9—H9B	0.9700
N1—C5	1.419 (2)	C6—C1	1.385 (3)
N1—H1A	0.8600	C6—H6A	0.9300
C5—C4	1.389 (2)	C2—C3	1.379 (3)
C5—C6	1.390 (3)	C2—C1	1.384 (3)
C8—C9	1.520 (2)	C2—H2A	0.9300
C8—H8A	0.9700	C3—H3A	0.9300
C8—H8B	0.9700	C10—H10A	0.9700
C11—C10	1.522 (3)	C10—H10B	0.9700
C11—H11A	0.9700	C1—H1B	0.9300
C11—H11B	0.9700
C7—N2—C11	123.08 (14)	C5—C4—H4A	120.2
C7—N2—C8	124.92 (14)	C8—C9—C10	103.46 (15)
C11—N2—C8	111.72 (13)	C8—C9—H9A	111.1
C7—N1—C5	125.40 (15)	C10—C9—H9A	111.1
C7—N1—H1A	117.3	C8—C9—H9B	111.1
C5—N1—H1A	117.3	C10—C9—H9B	111.1
N2—C7—N1	115.37 (15)	H9A—C9—H9B	109.0
N2—C7—S1	122.14 (13)	C1—C6—C5	119.56 (19)
N1—C7—S1	122.40 (13)	C1—C6—H6A	120.2
C4—C5—C6	119.98 (17)	C5—C6—H6A	120.2
C4—C5—N1	118.73 (16)	C3—C2—C1	119.36 (19)
C6—C5—N1	121.13 (16)	C3—C2—H2A	120.3
N2—C8—C9	103.50 (14)	C1—C2—H2A	120.3
N2—C8—H8A	111.1	C2—C3—C4	120.80 (19)
C9—C8—H8A	111.1	C2—C3—H3A	119.6
N2—C8—H8B	111.1	C4—C3—H3A	119.6
C9—C8—H8B	111.1	C11—C10—C9	103.05 (15)
H8A—C8—H8B	109.0	C11—C10—H10A	111.2
N2—C11—C10	103.34 (14)	C9—C10—H10A	111.2
N2—C11—H11A	111.1	C11—C10—H10B	111.2
C10—C11—H11A	111.1	C9—C10—H10B	111.2
N2—C11—H11B	111.1	H10A—C10—H10B	109.1
C10—C11—H11B	111.1	C2—C1—C6	120.7 (2)
H11A—C11—H11B	109.1	C2—C1—H1B	119.6
C3—C4—C5	119.51 (18)	C6—C1—H1B	119.6
C3—C4—H4A	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.86	2.64	3.4359 (17)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.86	2.64	3.4359 (17)	155

Symmetry code: (i) .