2-(2-Thien-yl)-4,5-dihydro-1H-imidazole.

In title compound, C(7)H(8)N(2)S, the five-membered rings are twisted by a dihedral angle of 5.17 (10)°. Two inter-molecular N-H⋯N and C-H⋯N hydrogen bonds to the same acceptor N atom form seven-membered rings, producing R(2) (1)(7) ring motifs. These inter-actions link neighbouring mol-ecules into one-dimensional chains extended along the c axis. The crystal structure is further stabilized by weak inter-molecular C-H⋯π inter-actions.

Related literature

For reference geometrical data, see: Allen et al. (1987 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a related structure and the synthesis, see, Kia et al. (2008 ▶); Stibrany et al. (2004 ▶). For the applications of imidazoline derivatives, see, for example: Blancafort (1978 ▶); Chan (1993 ▶); Vizi (1986 ▶); Li et al. (1996 ▶); Ueno et al. (1995 ▶); Corey & Grogan (1999 ▶).

Experimental

Crystal data

C7H8N2S

M = 152.21

Monoclinic,

a = 6.1321 (2) Å

b = 11.5663 (3) Å

c = 10.0098 (3) Å

β = 90.154 (1)°

V = 709.95 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 100.0 (1) K

0.54 × 0.28 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.825, T max = 0.922

27675 measured reflections

3100 independent reflections

3040 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.128

S = 1.24

3100 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001068/at2706sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001068/at2706Isup2.hkl

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

C7H8N2S	F(000) = 320
Mr = 152.21	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9869 reflections
a = 6.1321 (2) Å	θ = 2.5–34.3°
b = 11.5663 (3) Å	µ = 0.37 mm−1
c = 10.0098 (3) Å	T = 100 K
β = 90.154 (1)°	Block, colourless
V = 709.95 (4) Å3	0.54 × 0.28 × 0.22 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3100 independent reflections
Radiation source: fine-focus sealed tube	3040 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 35.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.825, Tmax = 0.922	k = −18→17
27675 measured reflections	l = −15→15

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.24	w = 1/[σ2(Fo2) + 1.7551P] where P = (Fo2 + 2Fc2)/3
3100 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.46967 (8)	0.14161 (4)	0.59514 (4)	0.01548 (10)
N2	0.0669 (2)	0.29635 (14)	0.61122 (15)	0.0137 (2)
N1	0.0460 (2)	0.30376 (14)	0.83746 (14)	0.0133 (2)
H1N1	0.0584	0.2724	0.9026	0.016*
C1	0.6387 (3)	0.05389 (17)	0.6858 (2)	0.0180 (3)
H1A	0.7542	0.0100	0.6482	0.022*
C2	0.5888 (3)	0.05418 (16)	0.81838 (19)	0.0169 (3)
H2A	0.6655	0.0103	0.8835	0.020*
C3	0.4092 (3)	0.12742 (15)	0.84860 (17)	0.0136 (3)
H3A	0.3530	0.1385	0.9360	0.016*
C4	0.3260 (3)	0.18060 (14)	0.73589 (16)	0.0117 (3)
C5	0.1427 (3)	0.26052 (14)	0.72556 (16)	0.0109 (3)
C6	−0.1543 (3)	0.36276 (17)	0.79447 (17)	0.0154 (3)
H6A	−0.1724	0.4380	0.8403	0.018*
H6B	−0.2849	0.3144	0.8101	0.018*
C7	−0.1097 (3)	0.37874 (16)	0.64419 (17)	0.0151 (3)
H7A	−0.2423	0.3615	0.5912	0.018*
H7B	−0.0634	0.4591	0.6252	0.018*

	U11	U22	U33	U12	U13	U23
S1	0.01727 (19)	0.01847 (19)	0.01071 (17)	0.00446 (15)	0.00185 (13)	−0.00026 (14)
N2	0.0153 (6)	0.0161 (6)	0.0098 (6)	0.0027 (5)	0.0003 (4)	0.0009 (5)
N1	0.0148 (6)	0.0170 (6)	0.0080 (5)	0.0029 (5)	0.0016 (4)	0.0004 (5)
C1	0.0166 (7)	0.0181 (8)	0.0192 (8)	0.0057 (6)	−0.0001 (6)	−0.0015 (6)
C2	0.0186 (7)	0.0155 (7)	0.0167 (7)	0.0029 (6)	−0.0034 (6)	0.0009 (6)
C3	0.0164 (7)	0.0129 (7)	0.0113 (6)	−0.0001 (5)	−0.0002 (5)	0.0004 (5)
C4	0.0131 (6)	0.0120 (6)	0.0100 (6)	0.0005 (5)	−0.0003 (5)	−0.0005 (5)
C5	0.0120 (6)	0.0113 (6)	0.0094 (6)	−0.0011 (5)	0.0005 (5)	−0.0004 (5)
C6	0.0143 (7)	0.0186 (7)	0.0132 (7)	0.0030 (6)	0.0019 (5)	0.0007 (6)
C7	0.0152 (7)	0.0181 (7)	0.0120 (7)	0.0035 (6)	0.0000 (5)	0.0018 (5)

S1—C1	1.7099 (19)	C2—H2A	0.9500
S1—C4	1.7239 (17)	C3—C4	1.381 (2)
N2—C5	1.302 (2)	C3—H3A	0.9500
N2—C7	1.480 (2)	C4—C5	1.459 (2)
N1—C5	1.364 (2)	C6—C7	1.541 (2)
N1—C6	1.468 (2)	C6—H6A	0.9900
N1—H1N1	0.7501	C6—H6B	0.9900
C1—C2	1.362 (3)	C7—H7A	0.9900
C1—H1A	0.9500	C7—H7B	0.9900
C2—C3	1.423 (3)
C1—S1—C4	91.82 (9)	C5—C4—S1	120.22 (12)
C5—N2—C7	105.57 (14)	N2—C5—N1	116.78 (15)
C5—N1—C6	107.14 (14)	N2—C5—C4	122.49 (15)
C5—N1—H1N1	119.6	N1—C5—C4	120.71 (14)
C6—N1—H1N1	124.2	N1—C6—C7	101.03 (13)
C2—C1—S1	112.21 (14)	N1—C6—H6A	111.6
C2—C1—H1A	123.9	C7—C6—H6A	111.6
S1—C1—H1A	123.9	N1—C6—H6B	111.6
C1—C2—C3	112.63 (16)	C7—C6—H6B	111.6
C1—C2—H2A	123.7	H6A—C6—H6B	109.4
C3—C2—H2A	123.7	N2—C7—C6	105.80 (14)
C4—C3—C2	112.08 (15)	N2—C7—H7A	110.6
C4—C3—H3A	124.0	C6—C7—H7A	110.6
C2—C3—H3A	124.0	N2—C7—H7B	110.6
C3—C4—C5	128.52 (15)	C6—C7—H7B	110.6
C3—C4—S1	111.26 (13)	H7A—C7—H7B	108.7
C4—S1—C1—C2	−0.16 (16)	C6—N1—C5—N2	11.9 (2)
S1—C1—C2—C3	−0.2 (2)	C6—N1—C5—C4	−169.73 (15)
C1—C2—C3—C4	0.5 (2)	C3—C4—C5—N2	−173.27 (18)
C2—C3—C4—C5	179.52 (17)	S1—C4—C5—N2	6.9 (2)
C2—C3—C4—S1	−0.60 (19)	C3—C4—C5—N1	8.5 (3)
C1—S1—C4—C3	0.44 (14)	S1—C4—C5—N1	−171.36 (13)
C1—S1—C4—C5	−179.67 (15)	C5—N1—C6—C7	−17.79 (18)
C7—N2—C5—N1	0.6 (2)	C5—N2—C7—C6	−12.26 (19)
C7—N2—C5—C4	−177.67 (15)	N1—C6—C7—N2	18.12 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2i	0.75	2.23	2.977 (2)	171
C3—H3A···N2i	0.95	2.60	3.482 (2)	155
C6—H6A···Cg1ii	0.99	2.89	3.539 (2)	124
C6—H6B···Cg1iii	0.99	2.83	3.691 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2i	0.75	2.23	2.977 (2)	171
C3—H3A⋯N2i	0.95	2.60	3.482 (2)	155
C6—H6A⋯Cg1ii	0.99	2.89	3.539 (2)	124
C6—H6B⋯Cg1iii	0.99	2.83	3.691 (2)	146

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the S1/C1–C4 (thiophen) ring.