N-Methyl­pyrrolidine-1-carbothio­amide

Umar, M.N.; Tahir, M.N.; Shoaib, M.; Ali, A.; Khan, I.

doi:10.1107/S1600536812020971

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1706

doi:10.1107/S1600536812020971

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N-Methylpyrrolidine-1-carbothioamide

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

^aDepartment of Chemistry, University of Malakand, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, ^cDepartment of Pharmacy, University of Malakand, Pakistan, and ^dDepartment of Biotechnology, University of Malakand, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 5 May 2012; accepted 8 May 2012; online 12 May 2012)

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 ).

Experimental

Crystal data

C₆H₁₂N₂S
M_r = 144.25
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.079
wR(F²) = 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

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) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) x, y, z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812020971/bq2355sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812020971/bq2355Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules are interlinked to form polymeric chains along the a-axis. The H-atoms not involved in H-bonding are omitted for clarity.

N-Methylpyrrolidine-1-carbothioamide top

Crystal data top

C₆H₁₂N₂S	Z = 4
M_r = 144.25	F(000) = 312
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.262	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1268P)² + 0.3916P] where P = (F_o² + 2F_c²)/3
2699 reflections	(Δ/σ)_max < 0.001
165 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₆H₁₂N₂S	γ = 76.177 (16)°
M_r = 144.25	V = 787.0 (3) Å³
Triclinic, P1	Z = 4
a = 8.616 (2) Å	Mo Kα radiation
b = 9.077 (2) Å	µ = 0.33 mm⁻¹
c = 10.796 (3) Å	T = 296 K
α = 73.725 (14)°	0.30 × 0.25 × 0.20 mm
β = 86.656 (15)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2699 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1385 reflections with I > 3σ(I)
T_min = 0.957, T_max = 0.966	R_int = 0.067
9119 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	0 restraints
wR(F²) = 0.262	H-atom parameters constrained
S = 1.04	Δρ_max = 0.43 e Å⁻³
2699 reflections	Δρ_min = −0.33 e Å⁻³
165 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₆H₁₂N₂S
M_r	144.25
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.616 (2), 9.077 (2), 10.796 (3)
α, β, γ (°)	73.725 (14), 86.656 (15), 76.177 (16)
V (Å³)	787.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.957, 0.966
No. of measured, independent and observed [I > 3σ(I)] reflections	9119, 2699, 1385
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.262, 1.04
No. of reflections	2699
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2ⁱ	0.86	2.73	3.472 (5)	144.8
N3—H4···S1ⁱⁱ	0.86	2.64	3.410 (5)	150.0
C12—H12B···S1ⁱⁱⁱ	0.97	2.84	3.765 (5)	158.8

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y, z+1.

Acknowledgements

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.

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