N-Cyclo­hexyl­pyrrolidine-1-carbothio­amide

Li, Y.-F.

doi:10.1107/S1600536812012627

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1220

doi:10.1107/S1600536812012627

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N-Cyclohexylpyrrolidine-1-carbothioamide

Yu-Feng Li ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: liyufeng8111@163.com

(Received 20 March 2012; accepted 23 March 2012; online 28 March 2012)

In the title molecule, C₁₁H₂₀N₂S, the five-membered ring has an envelope conformation and the cyclohexane ring is in a chair conformation. The N—H group is not involved in any intra- or intermolecular interactions.

Related literature

For the medicinal properties of pyrrolidine compounds, see: Yang et al. (1997 ). For related structures, see: Köhn et al. (2004 ); Li (2011 ).

Experimental

Crystal data

C₁₁H₂₀N₂S
M_r = 212.35
Orthorhombic, P b c a
a = 9.3808 (19) Å
b = 10.925 (2) Å
c = 23.540 (5) Å
V = 2412.6 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
22078 measured reflections
2766 independent reflections
1700 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.190
S = 1.18
2766 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812012627/lh5439sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012627/lh5439Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812012627/lh5439Isup3.cml

checkCIF report

Comment top

Pyrrolidine compounds have been shown to have medicinal properties (Yang et al., 1997). The molecular structure of the title compound is shown in Fig. 1. The five-membered ring has an envelope conformation with atom C2 forming the flap. The structures related compounds have been determined (Köhn et al., 2004; Li, 2011).

Related literature top

For the medicinal properties of pyrrolidine compounds, see: Yang et al. (1997). For related structures, see: Köhn et al. (2004); Li (2011).

Experimental top

A mixture of pyrrolidine (0.6 mol), and N-cyclohexylmethanethioamide (0.6 mol) was stirred in refluxing ethanol (14 ml) for 4 h to afford the title compound (0.51 mol, yield 85%). Colourless blocks of the title compound were obtained by recrystallization of a solution of the title compound ethanol at room temperature.

Structure description top

For the medicinal properties of pyrrolidine compounds, see: Yang et al. (1997). For related structures, see: Köhn et al. (2004); Li (2011).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids.

N-Cyclohexylpyrrolidine-1-carbothioamide top

Crystal data top

C₁₁H₂₀N₂S	F(000) = 928
M_r = 212.35	D_x = 1.169 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1700 reflections
a = 9.3808 (19) Å	θ = 3.4–27.5°
b = 10.925 (2) Å	µ = 0.24 mm⁻¹
c = 23.540 (5) Å	T = 293 K
V = 2412.6 (8) Å³	Block, colorless
Z = 8	0.22 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	1700 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 27.5°, θ_min = 3.4°
φ and ω scans	h = −12→12
22078 measured reflections	k = −13→14
2766 independent reflections	l = −30→30

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.1021P)²] where P = (F_o² + 2F_c²)/3
2766 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₁H₂₀N₂S	V = 2412.6 (8) Å³
M_r = 212.35	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.3808 (19) Å	µ = 0.24 mm⁻¹
b = 10.925 (2) Å	T = 293 K
c = 23.540 (5) Å	0.22 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	1700 reflections with I > 2σ(I)
22078 measured reflections	R_int = 0.046
2766 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.190	H-atom parameters constrained
S = 1.18	Δρ_max = 0.25 e Å⁻³
2766 reflections	Δρ_min = −0.35 e Å⁻³
127 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.07717 (8)	0.34275 (5)	0.16033 (2)	0.0727 (3)
N2	0.1756 (2)	0.57053 (15)	0.14966 (7)	0.0649 (5)
H2A	0.2105	0.6354	0.1650	0.078*
N1	0.1569 (2)	0.49963 (16)	0.24023 (7)	0.0625 (5)
C5	0.1402 (2)	0.47798 (18)	0.18465 (8)	0.0533 (5)
C6	0.1600 (2)	0.57042 (18)	0.08782 (8)	0.0565 (6)
H6A	0.0941	0.5046	0.0773	0.068*
C7	0.3007 (3)	0.54772 (19)	0.05863 (8)	0.0604 (6)
H7A	0.3378	0.4686	0.0701	0.072*
H7B	0.3687	0.6098	0.0702	0.072*
C9	0.2197 (3)	0.6700 (2)	−0.02522 (9)	0.0637 (6)
H9A	0.2865	0.7359	−0.0179	0.076*
H9B	0.2032	0.6664	−0.0659	0.076*
C10	0.0817 (2)	0.6969 (2)	0.00449 (10)	0.0647 (6)
H10A	0.0103	0.6382	−0.0076	0.078*
H10B	0.0490	0.7778	−0.0064	0.078*
C11	0.0964 (2)	0.6912 (2)	0.06890 (10)	0.0657 (6)
H11A	0.1569	0.7578	0.0817	0.079*
H11B	0.0034	0.7015	0.0862	0.079*
C8	0.2838 (3)	0.5505 (2)	−0.00562 (8)	0.0655 (6)
H8A	0.3763	0.5396	−0.0233	0.079*
H8B	0.2230	0.4834	−0.0175	0.079*
C4	0.2130 (3)	0.6141 (2)	0.26409 (9)	0.0751 (7)
H4A	0.1503	0.6824	0.2557	0.090*
H4B	0.3073	0.6319	0.2493	0.090*
C3	0.2184 (4)	0.5887 (3)	0.32761 (10)	0.0947 (10)
H3A	0.3120	0.5596	0.3388	0.114*
H3B	0.1960	0.6619	0.3492	0.114*
C2	0.1095 (5)	0.4934 (3)	0.33665 (10)	0.1053 (11)
H2B	0.0163	0.5302	0.3418	0.126*
H2C	0.1320	0.4451	0.3700	0.126*
C1	0.1110 (4)	0.4151 (3)	0.28475 (9)	0.0917 (9)
H1A	0.1776	0.3477	0.2888	0.110*
H1B	0.0169	0.3826	0.2768	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.1120 (6)	0.0526 (4)	0.0536 (4)	−0.0127 (3)	−0.0018 (3)	−0.0005 (2)
N2	0.0950 (14)	0.0592 (11)	0.0406 (9)	−0.0187 (10)	0.0007 (8)	−0.0041 (7)
N1	0.0922 (14)	0.0560 (10)	0.0393 (9)	0.0013 (9)	0.0052 (9)	−0.0024 (7)
C5	0.0651 (13)	0.0519 (11)	0.0429 (10)	0.0033 (9)	0.0023 (9)	−0.0004 (8)
C6	0.0732 (14)	0.0557 (12)	0.0408 (10)	−0.0137 (10)	−0.0010 (9)	−0.0014 (8)
C7	0.0765 (14)	0.0565 (12)	0.0482 (11)	0.0150 (10)	−0.0002 (10)	0.0070 (9)
C9	0.0625 (14)	0.0741 (14)	0.0545 (12)	−0.0005 (10)	−0.0019 (10)	0.0182 (10)
C10	0.0600 (14)	0.0720 (14)	0.0620 (13)	0.0034 (11)	−0.0089 (10)	0.0097 (11)
C11	0.0650 (14)	0.0706 (14)	0.0617 (13)	0.0093 (11)	0.0000 (10)	−0.0031 (11)
C8	0.0774 (15)	0.0722 (14)	0.0468 (11)	0.0104 (12)	0.0073 (10)	0.0057 (10)
C4	0.1016 (19)	0.0753 (14)	0.0484 (12)	−0.0030 (14)	−0.0013 (12)	−0.0143 (11)
C3	0.139 (3)	0.096 (2)	0.0492 (13)	0.0122 (19)	−0.0130 (15)	−0.0142 (12)
C2	0.155 (3)	0.119 (3)	0.0421 (14)	0.003 (2)	0.0090 (15)	0.0021 (14)
C1	0.156 (3)	0.0742 (17)	0.0452 (13)	−0.0016 (16)	0.0119 (14)	0.0066 (11)

Geometric parameters (Å, º) top

S1—C5	1.691 (2)	C10—H10A	0.9700
N2—C5	1.346 (3)	C10—H10B	0.9700
N2—C6	1.463 (2)	C11—H11A	0.9700
N2—H2A	0.8600	C11—H11B	0.9700
N1—C5	1.339 (3)	C8—H8A	0.9700
N1—C1	1.462 (3)	C8—H8B	0.9700
N1—C4	1.469 (3)	C4—C3	1.522 (3)
C6—C7	1.509 (3)	C4—H4A	0.9700
C6—C11	1.515 (3)	C4—H4B	0.9700
C6—H6A	0.9800	C3—C2	1.475 (4)
C7—C8	1.521 (3)	C3—H3A	0.9700
C7—H7A	0.9700	C3—H3B	0.9700
C7—H7B	0.9700	C2—C1	1.491 (4)
C9—C10	1.500 (3)	C2—H2B	0.9700
C9—C8	1.510 (3)	C2—H2C	0.9700
C9—H9A	0.9700	C1—H1A	0.9700
C9—H9B	0.9700	C1—H1B	0.9700
C10—C11	1.524 (3)

C5—N2—C6	125.71 (17)	C10—C11—H11A	109.4
C5—N2—H2A	117.1	C6—C11—H11B	109.4
C6—N2—H2A	117.1	C10—C11—H11B	109.4
C5—N1—C1	123.67 (19)	H11A—C11—H11B	108.0
C5—N1—C4	124.49 (18)	C9—C8—C7	111.29 (18)
C1—N1—C4	111.69 (18)	C9—C8—H8A	109.4
N1—C5—N2	115.87 (18)	C7—C8—H8A	109.4
N1—C5—S1	121.75 (16)	C9—C8—H8B	109.4
N2—C5—S1	122.37 (15)	C7—C8—H8B	109.4
N2—C6—C7	111.45 (17)	H8A—C8—H8B	108.0
N2—C6—C11	109.34 (16)	N1—C4—C3	103.42 (19)
C7—C6—C11	110.72 (16)	N1—C4—H4A	111.1
N2—C6—H6A	108.4	C3—C4—H4A	111.1
C7—C6—H6A	108.4	N1—C4—H4B	111.1
C11—C6—H6A	108.4	C3—C4—H4B	111.1
C6—C7—C8	110.99 (18)	H4A—C4—H4B	109.0
C6—C7—H7A	109.4	C2—C3—C4	104.3 (2)
C8—C7—H7A	109.4	C2—C3—H3A	110.9
C6—C7—H7B	109.4	C4—C3—H3A	110.9
C8—C7—H7B	109.4	C2—C3—H3B	110.9
H7A—C7—H7B	108.0	C4—C3—H3B	110.9
C10—C9—C8	111.75 (18)	H3A—C3—H3B	108.9
C10—C9—H9A	109.3	C3—C2—C1	106.3 (2)
C8—C9—H9A	109.3	C3—C2—H2B	110.5
C10—C9—H9B	109.3	C1—C2—H2B	110.5
C8—C9—H9B	109.3	C3—C2—H2C	110.5
H9A—C9—H9B	107.9	C1—C2—H2C	110.5
C9—C10—C11	112.17 (18)	H2B—C2—H2C	108.7
C9—C10—H10A	109.2	N1—C1—C2	103.2 (2)
C11—C10—H10A	109.2	N1—C1—H1A	111.1
C9—C10—H10B	109.2	C2—C1—H1A	111.1
C11—C10—H10B	109.2	N1—C1—H1B	111.1
H10A—C10—H10B	107.9	C2—C1—H1B	111.1
C6—C11—C10	111.34 (18)	H1A—C1—H1B	109.1
C6—C11—H11A	109.4

Experimental details

Crystal data
Chemical formula	C₁₁H₂₀N₂S
M_r	212.35
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	9.3808 (19), 10.925 (2), 23.540 (5)
V (Å³)	2412.6 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22078, 2766, 1700
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.190, 1.18
No. of reflections	2766
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.35

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors would like to thank the Natural Science Foundation of Shandong Province (No. ZR2010BL025).

References

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