N-Methyl­pyrrolidine-1-carbothio­amide

M Naveed Umar; M Nawaz Tahir; Mohammad Shoaib; Akbar Ali; Imran Khan

doi:10.1107/S1600536812020971

. 2012 May 12;68(Pt 6):o1706. doi: 10.1107/S1600536812020971

N-Methylpyrrolidine-1-carbothioamide

M Naveed Umar ^a, M Nawaz Tahir ^b,^*, Mohammad Shoaib ^c, Akbar Ali ^a, Imran Khan ^d

PMCID: PMC3379299 PMID: 22719497

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₆H₁₂N₂S, in which the N-methylthioformamide 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 molecules. The chains are interlinked by C—H⋯S hydrogen bonds.

Related literature

For a related structure, see: Jiang (2009 ▶). For graph–set notation, see: Bernstein et al. (1995 ▶). graphic file with name e-68-o1706-scheme1.jpg

Experimental

Crystal data

C₆H₁₂N₂S
M _r = 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
Δρ_max = 0.43 e Å⁻³
Δρ_min = −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.

Supplementary Material

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

e-68-o1706-sup1.cif^{(22.8KB, cif)}

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

e-68-o1706-Isup2.hkl^{(129.8KB, hkl)}

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

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

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

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. MNU, MS, AA and IK also gratefully acknowledge the financial support provided by the Higher Education Commission (HEC), Islamabad, Pakistan.

supplementary crystallographic information

Comment

The title compound (I), (Fig. 1) has been synthesized as a derivative. The crystal structure of N-phenylpyrrolidine-1-carbothioamide related to this structure (I) has been published previously (Jiang, 2009). In (I), two molecules in the asymmetric unit are present, which differ slightly from each other geometrically. In one molecule, the N-methylthioformamide moiety A (C1/N1/C2/S1) and the pyrrolidine ring B (N2/C3–C6) are planar with r.m.s. deviation of 0.0010 Å and 0.0360 Å, respectively. The dihedral angle between A/B is 5.88 (46)°. In second molecule, the similar groups C (C7/N3/C8/S2) and D (N4/C9—C12) are also planar with r.m.s. deviation of 0.0032 Å and 0.0839 Å, respectively and the dihedral angle between C/D is 5.92 (39)°. Both molecules are interlinked through classical intramolecular H–bonding of N—H···S type (Table 1, Fig. 2) with C(4) chains (Bernstein et al., 1995) to form zigzag infinite one-dimensional polymeric chains extending along the a-axis. The polymeric chains are interlinked due to C—H···S type of H–bonding (Table 1, Fig. 2).

Experimental

A solution of pyrrolidine (0.36 g, 5.00 mmol) in CH₃CN (3 ml) was added dropwise to a stirred solution of methyl isothiocyanate (0.47 ml, 5.50 mmol) in CH₃CN (10 ml, anhydrous) under cooling in an ice-bath to keep the reaction temperature below 283 K. The ice-bath was removed and stirring was continued at room temperature for 2 h to furnish a yellow-colored solution. The reaction mixture was extracted with ethylacetate and subjected to column chromatography to get the colorless product in 67% yield and then recrystalized with methanol to get colorless prisms of (I).