1-(2-Pyridyl)­pyrrolidine-2-thione

The title compound, C₉H₁₀N₂S, was prepared by thionation of 1-(2-pyridyl)­pyrrolidin-2-one with phospho­rus penta­sulfide. In the crystalline state, the plane of the pyrrolidine-2-thione ring is twisted by about 21° relative to the pyridine ring. In the crystal structure, mol­ecules are associated by π–π stacking.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.129
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999a); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1999b); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003) and SCHAKAL97 (Keller, 1997); software used to prepare material for publication: SHELXTL and PLATON.

1-(2-Pyridyl)pyrrolidine-2-thione

Crystal data

C9H10N2S	Z = 2
Mr = 178.25	F(000) = 188
Triclinic, P1	Dx = 1.368 Mg m^−3
Hall symbol: -P 1	Melting point = 363–368 K
a = 6.8504 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.3247 (9) Å	Cell parameters from 735 reflections
c = 9.5740 (11) Å	θ = 3.1–28.1°
α = 87.965 (2)°	µ = 0.32 mm^−1
β = 85.299 (2)°	T = 293 K
γ = 64.705 (2)°	Flat plate, pale yellow
V = 432.87 (9) Å^3	0.38 × 0.18 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1863 independent reflections
Radiation source: fine-focus sealed tube	1463 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→8
Tmin = 0.890, Tmax = 0.972	k = −9→9
2796 measured reflections	l = −9→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.068P)^2 + 0.0786P] where P = (Fo^2 + 2Fc^2)/3
1863 reflections	(Δ/σ)max = 0.001
109 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	1.26195 (9)	0.64579 (10)	0.12564 (6)	0.0637 (2)
N1	0.9022 (2)	0.7946 (2)	0.30892 (15)	0.0392 (4)
N1'	0.8595 (3)	0.7520 (2)	0.54710 (17)	0.0471 (4)
C2'	0.9956 (3)	0.7564 (3)	0.43998 (18)	0.0382 (4)
C2	1.0012 (3)	0.7535 (3)	0.1781 (2)	0.0446 (5)
C3'	1.2040 (3)	0.7335 (3)	0.4558 (2)	0.0480 (5)
H3'	1.2926	0.7406	0.3788	0.058*
C5	0.6645 (3)	0.8695 (3)	0.3093 (2)	0.0491 (5)
H5A	0.5907	0.9784	0.3761	0.059*
H5B	0.6201	0.7620	0.3317	0.059*
C4'	1.2768 (4)	0.6998 (3)	0.5887 (2)	0.0559 (5)
H4'	1.4165	0.6824	0.6025	0.067*
C3	0.8272 (4)	0.8139 (4)	0.0764 (2)	0.0580 (6)
H3A	0.8192	0.6957	0.0397	0.070*
H3B	0.8556	0.8900	−0.0013	0.070*
C6'	0.9358 (4)	0.7199 (3)	0.6744 (2)	0.0578 (6)
H6'	0.8438	0.7160	0.7503	0.069*
C5'	1.1406 (4)	0.6922 (3)	0.7005 (2)	0.0590 (6)
H5'	1.1860	0.6691	0.7910	0.071*
C4	0.6186 (3)	0.9435 (4)	0.1608 (2)	0.0592 (6)
H4A	0.5873	1.0856	0.1525	0.071*
H4B	0.4975	0.9235	0.1304	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0447 (3)	0.0899 (5)	0.0504 (4)	−0.0246 (3)	0.0100 (2)	−0.0077 (3)
N1	0.0320 (8)	0.0470 (9)	0.0390 (8)	−0.0175 (6)	0.0013 (6)	−0.0032 (6)
N1'	0.0456 (9)	0.0511 (9)	0.0412 (9)	−0.0185 (7)	0.0044 (7)	−0.0011 (7)
C2'	0.0379 (9)	0.0361 (9)	0.0386 (9)	−0.0139 (7)	−0.0001 (7)	−0.0043 (7)
C2	0.0435 (10)	0.0517 (11)	0.0393 (10)	−0.0219 (8)	0.0025 (8)	−0.0025 (8)
C3'	0.0417 (10)	0.0545 (12)	0.0480 (11)	−0.0207 (9)	−0.0008 (8)	−0.0071 (9)
C5	0.0333 (9)	0.0629 (12)	0.0496 (11)	−0.0197 (9)	0.0010 (8)	−0.0027 (9)
C4'	0.0485 (11)	0.0538 (12)	0.0608 (13)	−0.0150 (9)	−0.0143 (10)	−0.0094 (10)
C3	0.0533 (12)	0.0771 (15)	0.0419 (11)	−0.0257 (11)	−0.0051 (9)	−0.0038 (10)
C6'	0.0676 (15)	0.0587 (13)	0.0394 (11)	−0.0211 (11)	0.0034 (10)	0.0017 (9)
C5'	0.0687 (14)	0.0534 (12)	0.0440 (11)	−0.0137 (10)	−0.0128 (10)	−0.0039 (9)
C4	0.0424 (11)	0.0788 (15)	0.0535 (12)	−0.0220 (11)	−0.0101 (9)	0.0003 (10)

Geometric parameters (Å, º)

S1—C2	1.656 (2)	C5—H5B	0.9700
N1—C2	1.354 (2)	C4'—C5'	1.377 (3)
N1—C2'	1.420 (2)	C4'—H4'	0.9300
N1—C5	1.479 (2)	C3—C4	1.517 (3)
N1'—C2'	1.337 (2)	C3—H3A	0.9700
N1'—C6'	1.339 (3)	C3—H3B	0.9700
C2'—C3'	1.385 (3)	C6'—C5'	1.372 (3)
C2—C3	1.508 (3)	C6'—H6'	0.9300
C3'—C4'	1.380 (3)	C5'—H5'	0.9300
C3'—H3'	0.9300	C4—H4A	0.9700
C5—C4	1.512 (3)	C4—H4B	0.9700
C5—H5A	0.9700
C2—N1—C2'	129.16 (15)	C5'—C4'—H4'	120.3
C2—N1—C5	112.38 (15)	C3'—C4'—H4'	120.3
C2'—N1—C5	118.10 (15)	C2—C3—C4	105.17 (17)
C2'—N1'—C6'	116.43 (18)	C2—C3—H3A	110.7
N1'—C2'—C3'	123.45 (18)	C4—C3—H3A	110.7
N1'—C2'—N1	113.22 (16)	C2—C3—H3B	110.7
C3'—C2'—N1	123.29 (16)	C4—C3—H3B	110.7
N1—C2—C3	107.62 (17)	H3A—C3—H3B	108.8
N1—C2—S1	130.28 (15)	N1'—C6'—C5'	124.4 (2)
C3—C2—S1	122.02 (15)	N1'—C6'—H6'	117.8
C4'—C3'—C2'	118.30 (19)	C5'—C6'—H6'	117.8
C4'—C3'—H3'	120.9	C6'—C5'—C4'	118.0 (2)
C2'—C3'—H3'	120.9	C6'—C5'—H5'	121.0
N1—C5—C4	103.33 (15)	C4'—C5'—H5'	121.0
N1—C5—H5A	111.1	C5—C4—C3	103.34 (17)
C4—C5—H5A	111.1	C5—C4—H4A	111.1
N1—C5—H5B	111.1	C3—C4—H4A	111.1
C4—C5—H5B	111.1	C5—C4—H4B	111.1
H5A—C5—H5B	109.1	C3—C4—H4B	111.1
C5'—C4'—C3'	119.3 (2)	H4A—C4—H4B	109.1
C6'—N1'—C2'—C3'	−1.2 (3)	N1—C2'—C3'—C4'	179.03 (17)
C6'—N1'—C2'—N1	−178.95 (16)	C2—N1—C5—C4	−20.5 (2)
C2—N1—C2'—N1'	−158.79 (18)	C2'—N1—C5—C4	165.78 (17)
C5—N1—C2'—N1'	13.7 (2)	C2'—C3'—C4'—C5'	−0.7 (3)
C2—N1—C2'—C3'	23.5 (3)	N1—C2—C3—C4	14.4 (2)
C5—N1—C2'—C3'	−164.00 (18)	S1—C2—C3—C4	−168.54 (16)
C2'—N1—C2—C3	176.75 (18)	C2'—N1'—C6'—C5'	0.1 (3)
C5—N1—C2—C3	3.9 (2)	N1'—C6'—C5'—C4'	0.6 (3)
C2'—N1—C2—S1	0.0 (3)	C3'—C4'—C5'—C6'	−0.3 (3)
C5—N1—C2—S1	−172.86 (16)	N1—C5—C4—C3	27.7 (2)
N1'—C2'—C3'—C4'	1.5 (3)	C2—C3—C4—C5	−26.1 (2)