2-p-Tolyl-4,5-dihydro-1H-imidazole.

In the mol-ecule of the title compound, C(10)H(12)N(2), the six- and five-membered rings are almost co-planar, forming a dihedral angle of 3.56 (8)°. In the crystal structure, neighbouring mol-ecules are linked together by inter-molecular N-H⋯N hydrogen bonds into one-dimensional infinite chains along the c axis. The crystal structure, is further stabilized by weak inter-molecular C-H⋯π and π-π stacking [centroid-centroid distance = 3.8892 (9) Å] inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures and syntheses, see, Stibrany et al. (2004 ▶); Kia et al., 2008 ▶, 2009 ▶). For applications of imidazoline derivatives, see, for example: Blancafort (1978 ▶); Chan (1993 ▶); Vizi (1986 ▶); Li et al. (1996 ▶); Ueno et al., (1995 ▶); Corey & Grogan (1999 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H12N2

M = 160.22

Monoclinic,

a = 5.1134 (1) Å

b = 16.4020 (4) Å

c = 10.1712 (2) Å

β = 94.293 (1)°

V = 850.66 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.47 × 0.12 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.883, T max = 0.993

8503 measured reflections

1423 independent reflections

1338 reflections with I > 2˘I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.08

1423 reflections

114 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.21 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008125/at2738sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008125/at2738Isup2.hkl

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

C10H12N2	F(000) = 344
Mr = 160.22	Dx = 1.251 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3821 reflections
a = 5.1134 (1) Å	θ = 2.5–31.5°
b = 16.4020 (4) Å	µ = 0.08 mm−1
c = 10.1712 (2) Å	T = 100 K
β = 94.293 (1)°	Needle, colourless
V = 850.66 (3) Å3	0.47 × 0.12 × 0.09 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	1423 independent reflections
Radiation source: fine-focus sealed tube	1338 reflections with I > 2˘I)
graphite	Rint = 0.031
φ and ω scans	θmax = 31.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.883, Tmax = 0.993	k = −24→24
8503 measured reflections	l = −14→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0699P)2 + 0.0868P] where P = (Fo2 + 2Fc2)/3
1423 reflections	(Δ/σ)max < 0.001
114 parameters	Δρmax = 0.33 e Å−3
2 restraints	Δρmin = −0.21 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
N2	−0.2547 (3)	−0.01211 (8)	1.08200 (13)	0.0175 (3)
N1	−0.2444 (3)	−0.02899 (8)	0.86191 (12)	0.0189 (3)
C1	−0.4382 (3)	−0.07930 (9)	1.04580 (15)	0.0190 (3)
H1A	−0.6091	−0.0684	1.0774	0.023*
H1B	−0.3728	−0.1303	1.0837	0.023*
C2	−0.4570 (3)	−0.08371 (9)	0.89368 (15)	0.0181 (3)
H2A	−0.4279	−0.1388	0.8631	0.022*
H2B	−0.6256	−0.0644	0.8561	0.022*
C3	−0.1632 (3)	0.01280 (8)	0.97337 (13)	0.0142 (3)
C4	0.0262 (3)	0.08065 (8)	0.96924 (15)	0.0141 (2)
C5	0.1072 (3)	0.12199 (9)	1.08498 (14)	0.0189 (3)
H5A	0.0404	0.1069	1.1640	0.023*
C6	0.2870 (3)	0.18556 (9)	1.08343 (15)	0.0201 (3)
H6A	0.3393	0.2125	1.1615	0.024*
C7	0.3900 (3)	0.20952 (8)	0.96598 (14)	0.0171 (3)
C8	0.3049 (3)	0.16917 (9)	0.85050 (15)	0.0216 (3)
H8A	0.3690	0.1851	0.7712	0.026*
C9	0.1253 (3)	0.10529 (9)	0.85124 (15)	0.0202 (3)
H9A	0.0712	0.0790	0.7729	0.024*
C10	0.5915 (3)	0.27668 (9)	0.96448 (17)	0.0229 (3)
H10A	0.5467	0.3127	0.8918	0.034*
H10B	0.7613	0.2534	0.9550	0.034*
H10C	0.5946	0.3067	1.0456	0.034*
H1N1	−0.233 (5)	−0.0121 (14)	0.781 (3)	0.031 (6)*

	U11	U22	U33	U12	U13	U23
N2	0.0216 (6)	0.0188 (5)	0.0123 (5)	−0.0046 (5)	0.0029 (5)	0.0002 (4)
N1	0.0257 (7)	0.0208 (6)	0.0103 (5)	−0.0085 (5)	0.0011 (5)	−0.0010 (4)
C1	0.0227 (7)	0.0211 (6)	0.0134 (6)	−0.0059 (5)	0.0035 (5)	0.0005 (5)
C2	0.0201 (7)	0.0197 (6)	0.0145 (6)	−0.0052 (5)	0.0007 (5)	−0.0002 (5)
C3	0.0157 (6)	0.0148 (6)	0.0123 (6)	0.0002 (5)	0.0014 (5)	−0.0002 (4)
C4	0.0156 (6)	0.0147 (5)	0.0118 (5)	−0.0008 (4)	0.0004 (4)	0.0003 (4)
C5	0.0251 (8)	0.0204 (6)	0.0111 (6)	−0.0053 (6)	0.0009 (5)	0.0015 (5)
C6	0.0252 (8)	0.0224 (6)	0.0122 (6)	−0.0067 (6)	−0.0025 (6)	−0.0001 (5)
C7	0.0169 (7)	0.0173 (6)	0.0171 (6)	−0.0031 (5)	0.0011 (5)	0.0012 (5)
C8	0.0260 (8)	0.0233 (7)	0.0164 (6)	−0.0081 (6)	0.0076 (6)	−0.0009 (5)
C9	0.0257 (8)	0.0219 (6)	0.0134 (6)	−0.0074 (6)	0.0048 (5)	−0.0024 (5)
C10	0.0211 (8)	0.0226 (6)	0.0249 (7)	−0.0078 (6)	0.0008 (6)	0.0013 (6)

N2—C3	1.2976 (17)	C5—C6	1.391 (2)
N2—C1	1.4763 (19)	C5—H5A	0.9300
N1—C3	1.3627 (17)	C6—C7	1.3975 (19)
N1—C2	1.4641 (19)	C6—H6A	0.9300
N1—H1N1	0.87 (3)	C7—C8	1.389 (2)
C1—C2	1.5447 (19)	C7—C10	1.5092 (19)
C1—H1A	0.9700	C8—C9	1.394 (2)
C1—H1B	0.9700	C8—H8A	0.9300
C2—H2A	0.9700	C9—H9A	0.9300
C2—H2B	0.9700	C10—H10A	0.9600
C3—C4	1.4779 (18)	C10—H10B	0.9600
C4—C5	1.394 (2)	C10—H10C	0.9600
C4—C9	1.397 (2)
C3—N2—C1	106.60 (12)	C6—C5—C4	120.66 (13)
C3—N1—C2	108.04 (12)	C6—C5—H5A	119.7
C3—N1—H1N1	125.8 (17)	C4—C5—H5A	119.7
C2—N1—H1N1	120.4 (18)	C5—C6—C7	120.80 (13)
N2—C1—C2	105.98 (12)	C5—C6—H6A	119.6
N2—C1—H1A	110.5	C7—C6—H6A	119.6
C2—C1—H1A	110.5	C8—C7—C6	118.33 (13)
N2—C1—H1B	110.5	C8—C7—C10	120.66 (13)
C2—C1—H1B	110.5	C6—C7—C10	121.01 (13)
H1A—C1—H1B	108.7	C7—C8—C9	121.21 (13)
N1—C2—C1	101.59 (11)	C7—C8—H8A	119.4
N1—C2—H2A	111.5	C9—C8—H8A	119.4
C1—C2—H2A	111.5	C8—C9—C4	120.25 (14)
N1—C2—H2B	111.5	C8—C9—H9A	119.9
C1—C2—H2B	111.5	C4—C9—H9A	119.9
H2A—C2—H2B	109.3	C7—C10—H10A	109.5
N2—C3—N1	116.31 (12)	C7—C10—H10B	109.5
N2—C3—C4	122.68 (12)	H10A—C10—H10B	109.5
N1—C3—C4	120.98 (12)	C7—C10—H10C	109.5
C5—C4—C9	118.72 (12)	H10A—C10—H10C	109.5
C5—C4—C3	119.75 (13)	H10B—C10—H10C	109.5
C9—C4—C3	121.53 (13)
C3—N2—C1—C2	−5.19 (16)	C9—C4—C5—C6	−1.2 (2)
C3—N1—C2—C1	−11.95 (15)	C3—C4—C5—C6	179.46 (14)
N2—C1—C2—N1	10.31 (15)	C4—C5—C6—C7	0.1 (2)
C1—N2—C3—N1	−2.84 (18)	C5—C6—C7—C8	1.1 (2)
C1—N2—C3—C4	179.35 (13)	C5—C6—C7—C10	−178.05 (14)
C2—N1—C3—N2	10.16 (18)	C6—C7—C8—C9	−1.2 (2)
C2—N1—C3—C4	−171.99 (13)	C10—C7—C8—C9	177.91 (14)
N2—C3—C4—C5	−1.8 (2)	C7—C8—C9—C4	0.2 (2)
N1—C3—C4—C5	−179.56 (14)	C5—C4—C9—C8	1.0 (2)
N2—C3—C4—C9	178.80 (15)	C3—C4—C9—C8	−179.62 (14)
N1—C3—C4—C9	1.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2i	0.87 (3)	2.06 (3)	2.9224 (18)	170 (2)
C10—H10B···Cg1ii	0.96	2.88	3.8110 (16)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2i	0.87 (3)	2.06 (3)	2.9224 (18)	170 (2)
C10—H10B⋯Cg1ii	0.96	2.88	3.8110 (16)	163

Symmetry codes: (i) ; (ii) . Cg1 is the cetroid of the N1/C2/C1/N2/C3 ring.