2-(3-Chloro-phen-yl)-4,5-dihydro-1H-imidazole.

In the title compound, C(9)H(9)ClN(2), a substituted imidazoline, the six- and five-membered rings are twisted from each other, making a dihedral angle of 17.07 (5)°. In the crystal structure, a short Cl⋯Cl [3.3540 (3) Å] inter-action is observed. Neighbouring mol-ecules are linked together by inter-molecular N-H⋯N hydrogen bonds into a one-dimensional infinite chain along the [101] direction and short Cl⋯Cl contacts link the chains into a three-dimensional network. There is also a significant π-stacking inter-action between the planar sections of the six- and five-membered rings.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For a related structure and the synthesis, see: Stibrany et al. (2004 ▶); Kia et al. (2008 ▶). For the biological and pharmacological activities 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

C9H9ClN2

M = 180.63

Orthorhombic,

a = 19.7329 (8) Å

b = 39.1479 (18) Å

c = 4.3493 (2) Å

V = 3359.8 (3) Å3

Z = 16

Mo Kα radiation

μ = 0.39 mm−1

T = 100.0 (1) K

0.51 × 0.50 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.825, T max = 0.964

14166 measured reflections

3438 independent reflections

3224 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.072

S = 1.10

3438 reflections

113 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 1429 Friedel pairs

Flack parameter: −0.05 (4)

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/S1600536809001214/is2379sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001214/is2379Isup2.hkl

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

C9H9ClN2	F(000) = 1504
Mr = 180.63	Dx = 1.428 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 8962 reflections
a = 19.7329 (8) Å	θ = 2.9–36.7°
b = 39.1479 (18) Å	µ = 0.39 mm−1
c = 4.3493 (2) Å	T = 100 K
V = 3359.8 (3) Å3	Block, colourless
Z = 16	0.51 × 0.50 × 0.09 mm

Bruker APEXII CCD area-detector diffractometer	3438 independent reflections
Radiation source: fine-focus sealed tube	3224 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 35.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −31→25
Tmin = 0.825, Tmax = 0.964	k = −60→60
14166 measured reflections	l = −6→6

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.037P)2 + 1.1492P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
3438 reflections	Δρmax = 0.33 e Å−3
113 parameters	Δρmin = −0.15 e Å−3
1 restraint	Absolute structure: Flack (1983), 1429 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.05 (4)

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
Cl1	0.165233 (12)	0.246951 (6)	0.02330 (7)	0.02846 (7)
N1	0.00209 (4)	0.10678 (2)	0.1715 (2)	0.01782 (15)
N2	0.11053 (4)	0.11676 (2)	0.3205 (2)	0.01792 (15)
C1	0.10570 (4)	0.18532 (2)	0.0803 (2)	0.01732 (16)
H1A	0.1405	0.1803	0.2172	0.021*
C2	0.10314 (4)	0.21685 (2)	−0.0634 (2)	0.01837 (17)
C3	0.05234 (5)	0.22529 (2)	−0.2708 (2)	0.01901 (17)
H3A	0.0517	0.2465	−0.3667	0.023*
C4	0.00232 (5)	0.20104 (3)	−0.3313 (3)	0.01959 (17)
H4A	−0.0323	0.2062	−0.4686	0.024*
C5	0.00358 (5)	0.16926 (2)	−0.1890 (2)	0.01739 (16)
H5A	−0.0301	0.1533	−0.2313	0.021*
C6	0.05544 (4)	0.16118 (2)	0.0174 (2)	0.01498 (14)
C7	0.05755 (4)	0.12791 (2)	0.1766 (2)	0.01505 (15)
C8	0.01553 (5)	0.07848 (3)	0.3841 (3)	0.02052 (18)
H8A	0.0053	0.0566	0.2907	0.025*
H8B	−0.0102	0.0809	0.5728	0.025*
C9	0.09225 (5)	0.08268 (3)	0.4421 (3)	0.02013 (18)
H9A	0.1021	0.0813	0.6602	0.024*
H9B	0.1175	0.0650	0.3364	0.024*
H1N1	−0.0392 (8)	0.1159 (4)	0.148 (4)	0.036 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.01974 (10)	0.01899 (11)	0.04665 (16)	−0.00554 (8)	−0.00483 (11)	0.00392 (11)
N1	0.0124 (3)	0.0167 (4)	0.0244 (4)	−0.0016 (3)	−0.0022 (3)	0.0014 (3)
N2	0.0132 (3)	0.0161 (3)	0.0245 (4)	0.0007 (3)	−0.0013 (3)	0.0019 (3)
C1	0.0122 (3)	0.0165 (4)	0.0232 (4)	0.0008 (3)	−0.0002 (3)	−0.0003 (3)
C2	0.0139 (3)	0.0166 (4)	0.0246 (4)	−0.0010 (3)	0.0019 (3)	−0.0004 (3)
C3	0.0189 (4)	0.0171 (4)	0.0210 (4)	0.0013 (3)	0.0025 (3)	0.0013 (3)
C4	0.0180 (4)	0.0211 (4)	0.0196 (4)	0.0016 (3)	−0.0018 (3)	0.0000 (3)
C5	0.0148 (3)	0.0192 (4)	0.0181 (4)	0.0000 (3)	−0.0006 (3)	−0.0007 (3)
C6	0.0120 (3)	0.0149 (4)	0.0180 (4)	0.0012 (3)	0.0018 (3)	−0.0014 (3)
C7	0.0117 (3)	0.0158 (4)	0.0177 (4)	−0.0003 (3)	0.0011 (3)	−0.0016 (3)
C8	0.0164 (4)	0.0188 (4)	0.0264 (4)	−0.0021 (3)	−0.0011 (3)	0.0042 (3)
C9	0.0159 (4)	0.0184 (4)	0.0260 (5)	0.0002 (3)	−0.0008 (3)	0.0039 (3)

Cl1—C2	1.7413 (10)	C3—H3A	0.9300
N1—C7	1.3719 (12)	C4—C5	1.3897 (14)
N1—C8	1.4675 (13)	C4—H4A	0.9300
N1—H1N1	0.896 (16)	C5—C6	1.3976 (13)
N2—C7	1.2942 (12)	C5—H5A	0.9300
N2—C9	1.4799 (13)	C6—C7	1.4759 (13)
C1—C2	1.3844 (14)	C8—C9	1.5436 (13)
C1—C6	1.3969 (12)	C8—H8A	0.9700
C1—H1A	0.9300	C8—H8B	0.9700
C2—C3	1.3884 (14)	C9—H9A	0.9700
C3—C4	1.3944 (14)	C9—H9B	0.9700
Cl1···Cl1i	3.3540 (3)	C4···C6iii	3.3997 (15)
C1···C3ii	3.3945 (12)	C5···C7iii	3.3716 (12)
C1···C4ii	3.3301 (15)
C7—N1—C8	107.50 (7)	C1—C6—C5	119.51 (8)
C7—N1—H1N1	119.1 (10)	C1—C6—C7	119.03 (8)
C8—N1—H1N1	122.5 (11)	C5—C6—C7	121.45 (8)
C7—N2—C9	106.25 (7)	N2—C7—N1	116.68 (8)
C2—C1—C6	119.26 (9)	N2—C7—C6	123.17 (8)
C2—C1—H1A	120.4	N1—C7—C6	120.13 (8)
C6—C1—H1A	120.4	N1—C8—C9	101.53 (7)
C1—C2—C3	122.13 (9)	N1—C8—H8A	111.5
C1—C2—Cl1	118.68 (7)	C9—C8—H8A	111.5
C3—C2—Cl1	119.19 (8)	N1—C8—H8B	111.5
C2—C3—C4	118.15 (9)	C9—C8—H8B	111.5
C2—C3—H3A	120.9	H8A—C8—H8B	109.3
C4—C3—H3A	120.9	N2—C9—C8	106.06 (8)
C5—C4—C3	120.84 (9)	N2—C9—H9A	110.5
C5—C4—H4A	119.6	C8—C9—H9A	110.5
C3—C4—H4A	119.6	N2—C9—H9B	110.5
C4—C5—C6	120.12 (8)	C8—C9—H9B	110.5
C4—C5—H5A	119.9	H9A—C9—H9B	108.7
C6—C5—H5A	119.9
C6—C1—C2—C3	−0.48 (14)	C9—N2—C7—C6	−179.11 (8)
C6—C1—C2—Cl1	178.76 (7)	C8—N1—C7—N2	9.55 (12)
C1—C2—C3—C4	0.66 (14)	C8—N1—C7—C6	−171.73 (8)
Cl1—C2—C3—C4	−178.58 (8)	C1—C6—C7—N2	−15.38 (13)
C2—C3—C4—C5	−0.37 (15)	C5—C6—C7—N2	166.02 (9)
C3—C4—C5—C6	−0.09 (15)	C1—C6—C7—N1	165.98 (9)
C2—C1—C6—C5	0.00 (13)	C5—C6—C7—N1	−12.62 (13)
C2—C1—C6—C7	−178.62 (8)	C7—N1—C8—C9	−13.33 (10)
C4—C5—C6—C1	0.28 (14)	C7—N2—C9—C8	−8.35 (11)
C4—C5—C6—C7	178.87 (9)	N1—C8—C9—N2	13.08 (10)
C9—N2—C7—N1	−0.43 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2iv	0.896 (16)	2.118 (16)	3.0113 (11)	174.5 (15)

Table 1

Selected interatomic distances (Å)

Cl1⋯Cl1i	3.3540 (3)
C1⋯C3ii	3.3945 (12)
C1⋯C4ii	3.3301 (15)
C4⋯C6iii	3.3997 (15)
C5⋯C7iii	3.3716 (12)

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

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2iv	0.896 (16)	2.118 (16)	3.0113 (11)	174.5 (15)

Symmetry code: (iv) .