N-Methyl-pyrrolidine-1-carbothio-amide.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(6)H(12)N(2)S, in which the N-methyl-thio-formamide unit and the pyrrolidine ring mean plane are oriented at dihedral angles of 5.9 (5) and 5.9 (4)°. In the crystal, zigzag C(4) chains extending along the a axis are formed due to N-H⋯S hydrogen bonds between alternate arrangements of mol-ecules. The chains are inter-linked by C-H⋯S hydrogen bonds.

Related literature

For a related structure, see: Jiang (2009 ▶). For graph–set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C6H12N2S

M = 144.25

Triclinic,

a = 8.616 (2) Å

b = 9.077 (2) Å

c = 10.796 (3) Å

α = 73.725 (14)°

β = 86.656 (15)°

γ = 76.177 (16)°

V = 787.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.957, T max = 0.966

9119 measured reflections

2699 independent reflections

1385 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.262

S = 1.04

2699 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020971/bq2355sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020971/bq2355Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020971/bq2355Isup3.cml

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

C6H12N2S	Z = 4
Mr = 144.25	F(000) = 312
Triclinic, P1	Dx = 1.217 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.616 (2) Å	Cell parameters from 1204 reflections
b = 9.077 (2) Å	θ = 2.4–26.0°
c = 10.796 (3) Å	µ = 0.33 mm−1
α = 73.725 (14)°	T = 296 K
β = 86.656 (15)°	Prism, colorless
γ = 76.177 (16)°	0.30 × 0.25 × 0.20 mm
V = 787.0 (3) Å3

Bruker Kappa APEXII CCD diffractometer	2699 independent reflections
Radiation source: fine-focus sealed tube	1385 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.067
Detector resolution: 8.10 pixels mm-1	θmax = 25.0°, θmin = 2.4°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.957, Tmax = 0.966	l = −13→13
9119 measured reflections

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.262	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1268P)2 + 0.3916P] where P = (Fo2 + 2Fc2)/3
2699 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.4239 (8)	0.1340 (7)	0.3083 (6)	0.101 (2)
H1A	0.3186	0.1209	0.3350	0.151*
H1B	0.4965	0.0862	0.3803	0.151*
H1C	0.4586	0.0844	0.2406	0.151*
C2	0.3360 (6)	0.3972 (7)	0.1594 (5)	0.0699 (14)
C3	0.2574 (7)	0.6685 (8)	0.0191 (5)	0.0913 (18)
H3A	0.2961	0.6484	−0.0622	0.110*
H3B	0.1437	0.6732	0.0248	0.110*
C4	0.2906 (12)	0.8143 (10)	0.0304 (9)	0.153 (3)
H4A	0.3452	0.8611	−0.0463	0.184*
H4B	0.1906	0.8885	0.0365	0.184*
C5	0.3868 (11)	0.7860 (8)	0.1411 (7)	0.123 (3)
H5A	0.3265	0.8361	0.2030	0.148*
H5B	0.4801	0.8297	0.1166	0.148*
C6	0.4365 (7)	0.6143 (7)	0.1987 (5)	0.0846 (17)
H6A	0.4123	0.5869	0.2900	0.101*
H6B	0.5503	0.5764	0.1880	0.101*
C7	0.0612 (8)	0.8849 (7)	0.7020 (6)	0.0905 (18)
H7A	0.1661	0.8968	0.7156	0.136*
H7B	−0.0082	0.9109	0.7695	0.136*
H7C	0.0199	0.9542	0.6202	0.136*
C8	0.1664 (6)	0.6492 (6)	0.6253 (4)	0.0668 (14)
C9	0.2534 (7)	0.4014 (7)	0.5615 (5)	0.0791 (15)
H9A	0.3672	0.3846	0.5754	0.095*
H9B	0.2292	0.4497	0.4704	0.095*
C10	0.2012 (10)	0.2515 (9)	0.6076 (8)	0.126 (3)
H10A	0.1297	0.2437	0.5447	0.151*
H10B	0.2930	0.1627	0.6193	0.151*
C11	0.1210 (11)	0.2487 (8)	0.7269 (7)	0.125 (3)
H11A	0.1933	0.1864	0.7980	0.150*
H11B	0.0307	0.2009	0.7314	0.150*
C12	0.0651 (7)	0.4120 (6)	0.7365 (5)	0.0768 (15)
H12A	−0.0481	0.4515	0.7165	0.092*
H12B	0.0846	0.4183	0.8222	0.092*
N1	0.4210 (5)	0.2971 (5)	0.2626 (4)	0.0771 (13)
H1	0.4775	0.3348	0.3037	0.093*
N2	0.3437 (5)	0.5463 (6)	0.1280 (4)	0.0739 (12)
N3	0.0697 (5)	0.7250 (5)	0.7032 (4)	0.0746 (12)
H4	0.0100	0.6740	0.7564	0.089*
N4	0.1603 (5)	0.5002 (5)	0.6404 (4)	0.0677 (11)
S1	0.22218 (19)	0.3304 (2)	0.07310 (14)	0.0932 (6)
S2	0.28575 (19)	0.74016 (18)	0.51593 (13)	0.0881 (6)

	U11	U22	U33	U12	U13	U23
C1	0.122 (5)	0.099 (5)	0.083 (4)	−0.026 (4)	−0.013 (4)	−0.024 (4)
C2	0.071 (3)	0.102 (4)	0.040 (3)	−0.018 (3)	0.003 (2)	−0.027 (3)
C3	0.087 (4)	0.116 (5)	0.060 (3)	−0.020 (4)	−0.009 (3)	−0.007 (3)
C4	0.202 (10)	0.116 (6)	0.127 (7)	−0.046 (6)	−0.058 (7)	0.007 (5)
C5	0.180 (8)	0.100 (5)	0.095 (5)	−0.040 (5)	−0.017 (5)	−0.025 (4)
C6	0.102 (4)	0.107 (5)	0.052 (3)	−0.030 (4)	−0.004 (3)	−0.027 (3)
C7	0.115 (5)	0.085 (4)	0.078 (4)	−0.024 (3)	0.000 (3)	−0.032 (3)
C8	0.071 (3)	0.088 (4)	0.042 (3)	−0.018 (3)	−0.014 (2)	−0.016 (3)
C9	0.081 (4)	0.100 (4)	0.061 (3)	−0.013 (3)	−0.001 (3)	−0.035 (3)
C10	0.154 (7)	0.104 (5)	0.136 (7)	−0.036 (5)	0.023 (6)	−0.061 (5)
C11	0.187 (8)	0.088 (5)	0.109 (6)	−0.044 (5)	0.038 (5)	−0.036 (4)
C12	0.093 (4)	0.096 (4)	0.050 (3)	−0.038 (3)	0.000 (3)	−0.021 (3)
N1	0.088 (3)	0.093 (3)	0.054 (3)	−0.023 (3)	−0.011 (2)	−0.022 (2)
N2	0.081 (3)	0.098 (3)	0.041 (2)	−0.020 (3)	−0.009 (2)	−0.017 (2)
N3	0.090 (3)	0.086 (3)	0.055 (3)	−0.031 (2)	0.008 (2)	−0.023 (2)
N4	0.083 (3)	0.080 (3)	0.045 (2)	−0.021 (2)	−0.001 (2)	−0.023 (2)
S1	0.0962 (12)	0.1408 (15)	0.0594 (9)	−0.0374 (10)	−0.0056 (8)	−0.0447 (9)
S2	0.0935 (12)	0.1108 (13)	0.0601 (9)	−0.0357 (9)	0.0018 (8)	−0.0135 (8)

C1—N1	1.418 (7)	C7—H7A	0.9600
C1—H1A	0.9600	C7—H7B	0.9600
C1—H1B	0.9600	C7—H7C	0.9600
C1—H1C	0.9600	C8—N4	1.330 (6)
C2—N2	1.316 (6)	C8—N3	1.358 (6)
C2—N1	1.346 (6)	C8—S2	1.688 (5)
C2—S1	1.705 (5)	C9—N4	1.475 (6)
C3—C4	1.457 (9)	C9—C10	1.480 (9)
C3—N2	1.464 (7)	C9—H9A	0.9700
C3—H3A	0.9700	C9—H9B	0.9700
C3—H3B	0.9700	C10—C11	1.422 (10)
C4—C5	1.423 (10)	C10—H10A	0.9700
C4—H4A	0.9700	C10—H10B	0.9700
C4—H4B	0.9700	C11—C12	1.476 (8)
C5—C6	1.473 (8)	C11—H11A	0.9700
C5—H5A	0.9700	C11—H11B	0.9700
C5—H5B	0.9700	C12—N4	1.462 (6)
C6—N2	1.474 (6)	C12—H12A	0.9700
C6—H6A	0.9700	C12—H12B	0.9700
C6—H6B	0.9700	N1—H1	0.8600
C7—N3	1.432 (6)	N3—H4	0.8600
N1—C1—H1A	109.5	N4—C8—N3	115.8 (5)
N1—C1—H1B	109.5	N4—C8—S2	122.6 (4)
H1A—C1—H1B	109.5	N3—C8—S2	121.6 (4)
N1—C1—H1C	109.5	N4—C9—C10	103.7 (5)
H1A—C1—H1C	109.5	N4—C9—H9A	111.0
H1B—C1—H1C	109.5	C10—C9—H9A	111.0
N2—C2—N1	118.2 (4)	N4—C9—H9B	111.0
N2—C2—S1	121.6 (4)	C10—C9—H9B	111.0
N1—C2—S1	120.2 (4)	H9A—C9—H9B	109.0
C4—C3—N2	104.4 (5)	C11—C10—C9	108.4 (6)
C4—C3—H3A	110.9	C11—C10—H10A	110.0
N2—C3—H3A	110.9	C9—C10—H10A	110.0
C4—C3—H3B	110.9	C11—C10—H10B	110.0
N2—C3—H3B	110.9	C9—C10—H10B	110.0
H3A—C3—H3B	108.9	H10A—C10—H10B	108.4
C5—C4—C3	111.2 (6)	C10—C11—C12	108.9 (6)
C5—C4—H4A	109.4	C10—C11—H11A	109.9
C3—C4—H4A	109.4	C12—C11—H11A	109.9
C5—C4—H4B	109.4	C10—C11—H11B	109.9
C3—C4—H4B	109.4	C12—C11—H11B	109.9
H4A—C4—H4B	108.0	H11A—C11—H11B	108.3
C4—C5—C6	108.3 (6)	N4—C12—C11	103.6 (5)
C4—C5—H5A	110.0	N4—C12—H12A	111.0
C6—C5—H5A	110.0	C11—C12—H12A	111.0
C4—C5—H5B	110.0	N4—C12—H12B	111.0
C6—C5—H5B	110.0	C11—C12—H12B	111.0
H5A—C5—H5B	108.4	H12A—C12—H12B	109.0
C5—C6—N2	104.9 (5)	C2—N1—C1	124.6 (5)
C5—C6—H6A	110.8	C2—N1—H1	117.7
N2—C6—H6A	110.8	C1—N1—H1	117.7
C5—C6—H6B	110.8	C2—N2—C3	124.3 (5)
N2—C6—H6B	110.8	C2—N2—C6	125.1 (4)
H6A—C6—H6B	108.8	C3—N2—C6	110.6 (5)
N3—C7—H7A	109.5	C8—N3—C7	123.9 (5)
N3—C7—H7B	109.5	C8—N3—H4	118.0
H7A—C7—H7B	109.5	C7—N3—H4	118.0
N3—C7—H7C	109.5	C8—N4—C12	125.5 (4)
H7A—C7—H7C	109.5	C8—N4—C9	123.2 (4)
H7B—C7—H7C	109.5	C12—N4—C9	111.3 (4)
N2—C3—C4—C5	−1.7 (10)	C4—C3—N2—C6	−4.0 (7)
C3—C4—C5—C6	6.6 (11)	C5—C6—N2—C2	−170.9 (6)
C4—C5—C6—N2	−8.6 (8)	C5—C6—N2—C3	7.8 (6)
N4—C9—C10—C11	−15.4 (8)	N4—C8—N3—C7	179.3 (5)
C9—C10—C11—C12	21.4 (10)	S2—C8—N3—C7	−1.0 (7)
C10—C11—C12—N4	−17.9 (8)	N3—C8—N4—C12	−3.0 (7)
N2—C2—N1—C1	179.6 (5)	S2—C8—N4—C12	177.3 (4)
S1—C2—N1—C1	−0.3 (7)	N3—C8—N4—C9	178.1 (4)
N1—C2—N2—C3	−179.7 (5)	S2—C8—N4—C9	−1.6 (6)
S1—C2—N2—C3	0.3 (7)	C11—C12—N4—C8	−170.9 (5)
N1—C2—N2—C6	−1.1 (8)	C11—C12—N4—C9	8.1 (6)
S1—C2—N2—C6	178.8 (4)	C10—C9—N4—C8	−176.9 (5)
C4—C3—N2—C2	174.7 (6)	C10—C9—N4—C12	4.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2i	0.86	2.73	3.472 (5)	145
N3—H4···S1ii	0.86	2.64	3.410 (5)	150
C12—H12B···S1iii	0.97	2.84	3.765 (5)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2i	0.86	2.73	3.472 (5)	145
N3—H4⋯S1ii	0.86	2.64	3.410 (5)	150
C12—H12B⋯S1iii	0.97	2.84	3.765 (5)	159

Symmetry codes: (i) ; (ii) ; (iii) .