N-(Pyrrolidin-1-ylcarbothio-yl)benzamide.

In the title compound, C(12)H(14)N(2)OS, the pyrrolidine ring adopts an envelope conformation with the C atom at the 3-position as the flap and makes a dihedral angle of 65.80 (9)° with the benzene ring. In the crystal, N-H⋯O hydrogen bonds join c-glide related mol-ecules into chains extended along [001] that are further connected into (100) layers via C-H⋯O inter-actions.

Related literature

For related compounds, their structural parameters and chemical properties, see: Al-abbasi et al. (2010 ▶, 2011 ▶); Al-abbasi & Kassim (2011 ▶); Ngah et al. (2006 ▶).

Experimental

Crystal data

C12H14N2OS

M = 234.31

Monoclinic,

a = 10.3666 (4) Å

b = 14.6008 (5) Å

c = 7.8240 (3) Å

β = 98.446 (4)°

V = 1171.40 (8) Å3

Z = 4

Cu Kα radiation

μ = 2.29 mm−1

T = 150 K

0.13 × 0.06 × 0.03 mm

Data collection

Oxford Diffraction Gemini area-detector diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.870, T max = 0.934

8077 measured reflections

2245 independent reflections

1958 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.03

2245 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; 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: SHELXTL, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811053694/gk2440sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053694/gk2440Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053694/gk2440Isup3.cml

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

C12H14N2OS	F(000) = 496
Mr = 234.31	Dx = 1.329 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3639 reflections
a = 10.3666 (4) Å	θ = 4–71.2°
b = 14.6008 (5) Å	µ = 2.29 mm−1
c = 7.8240 (3) Å	T = 150 K
β = 98.446 (4)°	Needle, colourless
V = 1171.40 (8) Å3	0.13 × 0.06 × 0.03 mm
Z = 4

Oxford Diffraction Gemini area-detector diffractometer	2245 independent reflections
Radiation source: fine-focus sealed tube	1958 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 0 pixels mm-1	θmax = 71.2°, θmin = 4.3°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −17→17
Tmin = 0.870, Tmax = 0.934	l = −9→9
8077 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.4389P] where P = (Fo2 + 2Fc2)/3
2245 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K.(Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst., 105, 107.)

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	−0.07552 (4)	0.14802 (3)	0.15309 (5)	0.02646 (15)
O1	0.19040 (11)	0.34576 (8)	0.07829 (14)	0.0257 (3)
N1	0.10339 (13)	0.27023 (9)	0.28912 (17)	0.0225 (3)
H1	0.1201	0.2472	0.3911	0.027*
N2	−0.08955 (12)	0.32949 (10)	0.14768 (16)	0.0221 (3)
C1	0.30423 (16)	0.36102 (11)	0.5288 (2)	0.0258 (4)
H1A	0.2228	0.3603	0.5651	0.031*
C2	0.41496 (17)	0.38288 (13)	0.6445 (2)	0.0313 (4)
H2	0.4074	0.3981	0.7580	0.038*
C3	0.53634 (17)	0.38203 (13)	0.5908 (3)	0.0340 (4)
H3	0.6104	0.3956	0.6690	0.041*
C4	0.54804 (17)	0.36105 (13)	0.4211 (3)	0.0326 (4)
H4	0.6300	0.3601	0.3861	0.039*
C5	0.43831 (16)	0.34158 (12)	0.3035 (2)	0.0288 (4)
H5	0.4459	0.3295	0.1887	0.035*
C6	0.31615 (15)	0.34018 (11)	0.3581 (2)	0.0235 (3)
C7	0.19885 (15)	0.31944 (11)	0.2285 (2)	0.0221 (3)
C8	−0.02146 (15)	0.25496 (11)	0.19383 (19)	0.0215 (3)
C9	−0.22292 (15)	0.32549 (12)	0.0516 (2)	0.0256 (3)
H9A	−0.2807	0.2921	0.1162	0.031*
H9B	−0.2236	0.2965	−0.0600	0.031*
C10	−0.26313 (17)	0.42580 (13)	0.0310 (2)	0.0309 (4)
H10A	−0.3556	0.4330	0.0351	0.037*
H10B	−0.2434	0.4503	−0.0775	0.037*
C11	−0.18200 (16)	0.47345 (12)	0.1844 (2)	0.0283 (4)
H11A	−0.1726	0.5383	0.1621	0.034*
H11B	−0.2210	0.4659	0.2889	0.034*
C12	−0.05187 (16)	0.42453 (11)	0.1987 (2)	0.0257 (4)
H12A	0.0028	0.4511	0.1211	0.031*
H12B	−0.0059	0.4268	0.3159	0.031*

	U11	U22	U33	U12	U13	U23
S1	0.0244 (2)	0.0229 (2)	0.0312 (2)	−0.00252 (14)	0.00082 (16)	−0.00183 (14)
O1	0.0254 (6)	0.0300 (6)	0.0211 (6)	−0.0026 (4)	0.0011 (4)	0.0003 (4)
N1	0.0208 (6)	0.0272 (7)	0.0182 (6)	−0.0020 (5)	−0.0012 (5)	0.0017 (5)
N2	0.0204 (6)	0.0237 (7)	0.0214 (7)	−0.0030 (5)	0.0002 (5)	−0.0005 (5)
C1	0.0241 (8)	0.0263 (8)	0.0263 (8)	0.0006 (6)	0.0014 (7)	−0.0012 (6)
C2	0.0325 (9)	0.0311 (9)	0.0277 (9)	0.0002 (7)	−0.0039 (7)	−0.0043 (7)
C3	0.0257 (9)	0.0313 (9)	0.0403 (10)	−0.0018 (7)	−0.0105 (7)	−0.0024 (7)
C4	0.0205 (8)	0.0323 (9)	0.0447 (11)	−0.0021 (7)	0.0038 (7)	−0.0001 (8)
C5	0.0249 (8)	0.0317 (9)	0.0296 (9)	−0.0015 (6)	0.0036 (7)	−0.0018 (7)
C6	0.0220 (8)	0.0224 (8)	0.0250 (8)	−0.0005 (6)	−0.0003 (6)	−0.0002 (6)
C7	0.0207 (7)	0.0218 (8)	0.0233 (8)	0.0010 (6)	0.0016 (6)	−0.0024 (6)
C8	0.0212 (8)	0.0263 (8)	0.0173 (7)	−0.0020 (6)	0.0035 (6)	0.0003 (6)
C9	0.0193 (8)	0.0315 (9)	0.0248 (8)	−0.0027 (6)	−0.0005 (6)	−0.0012 (7)
C10	0.0250 (8)	0.0330 (10)	0.0330 (9)	0.0022 (7)	−0.0012 (7)	0.0016 (7)
C11	0.0283 (8)	0.0261 (9)	0.0299 (8)	0.0004 (6)	0.0027 (7)	0.0012 (7)
C12	0.0261 (8)	0.0219 (8)	0.0281 (8)	−0.0030 (6)	0.0001 (6)	0.0002 (6)

S1—C8	1.6737 (16)	C4—H4	0.9300
O1—C7	1.2275 (19)	C5—C6	1.395 (2)
N1—C7	1.363 (2)	C5—H5	0.9300
N1—C8	1.413 (2)	C6—C7	1.496 (2)
N1—H1	0.8600	C9—C10	1.525 (2)
N2—C8	1.318 (2)	C9—H9A	0.9700
N2—C9	1.4746 (19)	C9—H9B	0.9700
N2—C12	1.480 (2)	C10—C11	1.528 (2)
C1—C2	1.391 (2)	C10—H10A	0.9700
C1—C6	1.392 (2)	C10—H10B	0.9700
C1—H1A	0.9300	C11—C12	1.516 (2)
C2—C3	1.384 (3)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.385 (3)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.384 (2)
C7—N1—C8	123.71 (13)	N2—C8—N1	115.24 (14)
C7—N1—H1	118.1	N2—C8—S1	124.55 (12)
C8—N1—H1	118.1	N1—C8—S1	120.18 (12)
C8—N2—C9	122.08 (14)	N2—C9—C10	103.72 (13)
C8—N2—C12	126.18 (13)	N2—C9—H9A	111.0
C9—N2—C12	111.41 (13)	C10—C9—H9A	111.0
C2—C1—C6	119.56 (16)	N2—C9—H9B	111.0
C2—C1—H1A	120.2	C10—C9—H9B	111.0
C6—C1—H1A	120.2	H9A—C9—H9B	109.0
C3—C2—C1	120.06 (17)	C9—C10—C11	104.10 (13)
C3—C2—H2	120.0	C9—C10—H10A	110.9
C1—C2—H2	120.0	C11—C10—H10A	110.9
C2—C3—C4	120.29 (16)	C9—C10—H10B	110.9
C2—C3—H3	119.9	C11—C10—H10B	110.9
C4—C3—H3	119.9	H10A—C10—H10B	109.0
C5—C4—C3	120.25 (17)	C12—C11—C10	102.97 (14)
C5—C4—H4	119.9	C12—C11—H11A	111.2
C3—C4—H4	119.9	C10—C11—H11A	111.2
C4—C5—C6	119.58 (17)	C12—C11—H11B	111.2
C4—C5—H5	120.2	C10—C11—H11B	111.2
C6—C5—H5	120.2	H11A—C11—H11B	109.1
C1—C6—C5	120.22 (15)	N2—C12—C11	103.01 (13)
C1—C6—C7	121.10 (14)	N2—C12—H12A	111.2
C5—C6—C7	118.64 (15)	C11—C12—H12A	111.2
O1—C7—N1	123.00 (14)	N2—C12—H12B	111.2
O1—C7—C6	121.50 (14)	C11—C12—H12B	111.2
N1—C7—C6	115.49 (14)	H12A—C12—H12B	109.1
C6—C1—C2—C3	−1.3 (3)	C9—N2—C8—N1	−178.38 (13)
C1—C2—C3—C4	1.2 (3)	C12—N2—C8—N1	−5.5 (2)
C2—C3—C4—C5	0.6 (3)	C9—N2—C8—S1	−0.6 (2)
C3—C4—C5—C6	−2.1 (3)	C12—N2—C8—S1	172.25 (12)
C2—C1—C6—C5	−0.3 (3)	C7—N1—C8—N2	−59.7 (2)
C2—C1—C6—C7	−177.91 (15)	C7—N1—C8—S1	122.50 (15)
C4—C5—C6—C1	2.0 (3)	C8—N2—C9—C10	178.74 (14)
C4—C5—C6—C7	179.69 (15)	C12—N2—C9—C10	4.89 (17)
C8—N1—C7—O1	−8.9 (2)	N2—C9—C10—C11	−26.57 (16)
C8—N1—C7—C6	170.83 (14)	C9—C10—C11—C12	38.33 (17)
C1—C6—C7—O1	142.08 (16)	C8—N2—C12—C11	−154.72 (15)
C5—C6—C7—O1	−35.6 (2)	C9—N2—C12—C11	18.82 (17)
C1—C6—C7—N1	−37.7 (2)	C10—C11—C12—N2	−34.56 (16)
C5—C6—C7—N1	144.65 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.05	2.8637 (17)	157
C11—H11A···O1ii	0.97	2.52	3.339 (2)	142
C12—H12A···O1	0.97	2.54	3.035 (2)	112

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.05	2.8637 (17)	157
C11—H11A⋯O1ii	0.97	2.52	3.339 (2)	142

Symmetry codes: (i) ; (ii) .