1-(3-Meth-oxy-phen-yl)-4,5-dimethyl-2-phenyl-1H-imidazole.

In the title compound, C18H18N2O, the imidazole ring makes dihedral angles of 68.26 (7) and 22.45 (9)° with the meth-oxy-phenyl and phenyl rings, respectively. The dihedral angle between the meth-oxy-phenyl and phenyl ring is 71.86 (7)°. In the crystal, weak inter-molecular C-H⋯O and C-H⋯N hydrogen bonds link the mol-ecules into columns propagated in [101].

Related literature

For related structures, see: Gayathri et al. (2010 ▶); Rosepriya et al. (2011 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H18N2O

M = 278.34

Triclinic,

a = 8.0199 (1) Å

b = 9.4807 (1) Å

c = 10.4971 (2) Å

α = 108.339 (1)°

β = 94.910 (1)°

γ = 90.535 (1)°

V = 754.27 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.35 × 0.30 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.974, T max = 0.977

14252 measured reflections

2644 independent reflections

2159 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.148

S = 1.04

2644 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016966/cv5418sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016966/cv5418Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016966/cv5418Isup3.cml

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

C18H18N2O	Z = 2
Mr = 278.34	F(000) = 296
Triclinic, P1	Dx = 1.226 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0199 (1) Å	Cell parameters from 2644 reflections
b = 9.4807 (1) Å	θ = 2.3–30.6°
c = 10.4971 (2) Å	µ = 0.08 mm−1
α = 108.339 (1)°	T = 293 K
β = 94.910 (1)°	Block, colourless
γ = 90.535 (1)°	0.35 × 0.30 × 0.30 mm
V = 754.27 (2) Å3

Bruker Kappa APEXII CCD diffractometer	2644 independent reflections
Radiation source: fine-focus sealed tube	2159 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω and φ scan	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
Tmin = 0.974, Tmax = 0.977	k = −11→11
14252 measured reflections	l = −12→12

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0747P)2 + 0.2805P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2644 reflections	Δρmax = 0.33 e Å−3
191 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (7)

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
C1	0.7362 (2)	0.4690 (2)	−0.02515 (17)	0.0442 (4)
C2	0.7291 (3)	0.7075 (2)	0.05116 (19)	0.0521 (5)
C3	0.7842 (3)	0.6639 (2)	0.15818 (19)	0.0513 (5)
C4	0.6975 (4)	0.8605 (2)	0.0466 (3)	0.0792 (7)
H4A	0.6594	0.8561	−0.0438	0.119*
H4B	0.7993	0.9205	0.0751	0.119*
H4C	0.6135	0.9036	0.1057	0.119*
C5	0.8313 (3)	0.7516 (3)	0.3018 (2)	0.0713 (7)
H5A	0.8654	0.6856	0.3514	0.107*
H5B	0.7368	0.8053	0.3393	0.107*
H5C	0.9222	0.8206	0.3072	0.107*
C6	0.8135 (2)	0.4174 (2)	0.19308 (17)	0.0440 (4)
C7	0.6791 (2)	0.3354 (2)	0.21018 (19)	0.0500 (5)
H7	0.5731	0.3408	0.1689	0.060*
C8	0.7059 (3)	0.2451 (2)	0.2900 (2)	0.0569 (5)
H8	0.6170	0.1879	0.3015	0.068*
C9	0.8613 (3)	0.2385 (2)	0.3528 (2)	0.0557 (5)
H9	0.8773	0.1770	0.4061	0.067*
C10	0.9949 (2)	0.3234 (2)	0.33671 (17)	0.0483 (5)
C11	0.9717 (2)	0.4125 (2)	0.25552 (17)	0.0466 (5)
H11	1.0610	0.4685	0.2429	0.056*
C12	1.2812 (3)	0.4015 (3)	0.3979 (2)	0.0701 (6)
H12A	1.3781	0.3800	0.4479	0.105*
H12B	1.2553	0.5040	0.4365	0.105*
H12C	1.3037	0.3830	0.3058	0.105*
C13	0.7294 (2)	0.3179 (2)	−0.12117 (18)	0.0482 (5)
C14	0.8223 (3)	0.2026 (2)	−0.1019 (2)	0.0621 (6)
H14	0.8895	0.2175	−0.0217	0.075*
C15	0.8159 (3)	0.0654 (3)	−0.2010 (3)	0.0743 (7)
H15	0.8778	−0.0114	−0.1864	0.089*
C16	0.7189 (4)	0.0416 (3)	−0.3206 (3)	0.0770 (7)
H16	0.7157	−0.0505	−0.3872	0.092*
C17	0.6270 (3)	0.1548 (3)	−0.3408 (2)	0.0765 (7)
H17	0.5617	0.1395	−0.4219	0.092*
C18	0.6304 (3)	0.2911 (2)	−0.2422 (2)	0.0611 (6)
H18	0.5654	0.3663	−0.2568	0.073*
N1	0.78868 (18)	0.51065 (17)	0.10977 (14)	0.0450 (4)
N2	0.70075 (19)	0.58661 (17)	−0.06211 (15)	0.0489 (4)
O1	1.14352 (18)	0.30952 (17)	0.40312 (15)	0.0643 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0460 (9)	0.0516 (11)	0.0371 (9)	0.0035 (7)	0.0034 (7)	0.0172 (8)
C2	0.0646 (12)	0.0465 (11)	0.0461 (11)	−0.0015 (8)	−0.0005 (8)	0.0172 (9)
C3	0.0627 (12)	0.0481 (11)	0.0416 (10)	−0.0036 (8)	−0.0016 (8)	0.0140 (8)
C4	0.119 (2)	0.0510 (13)	0.0667 (15)	−0.0024 (13)	−0.0097 (14)	0.0222 (11)
C5	0.1036 (18)	0.0594 (13)	0.0453 (12)	−0.0065 (12)	−0.0068 (11)	0.0125 (10)
C6	0.0527 (10)	0.0467 (10)	0.0339 (9)	0.0052 (8)	0.0062 (7)	0.0141 (8)
C7	0.0503 (10)	0.0528 (11)	0.0474 (10)	0.0035 (8)	0.0058 (8)	0.0163 (9)
C8	0.0627 (12)	0.0527 (12)	0.0594 (12)	−0.0002 (9)	0.0132 (9)	0.0217 (10)
C9	0.0733 (13)	0.0490 (11)	0.0520 (11)	0.0099 (9)	0.0110 (9)	0.0246 (9)
C10	0.0579 (11)	0.0516 (11)	0.0357 (9)	0.0134 (8)	0.0049 (8)	0.0136 (8)
C11	0.0499 (10)	0.0529 (11)	0.0395 (9)	0.0028 (8)	0.0061 (7)	0.0175 (8)
C12	0.0587 (13)	0.0918 (17)	0.0619 (14)	0.0079 (11)	−0.0043 (10)	0.0295 (13)
C13	0.0544 (10)	0.0507 (11)	0.0417 (10)	0.0035 (8)	0.0101 (8)	0.0162 (9)
C14	0.0744 (14)	0.0645 (14)	0.0477 (11)	0.0183 (11)	0.0104 (10)	0.0166 (10)
C15	0.0971 (18)	0.0581 (14)	0.0686 (15)	0.0237 (12)	0.0217 (13)	0.0173 (12)
C16	0.1025 (19)	0.0565 (14)	0.0621 (15)	0.0029 (12)	0.0126 (13)	0.0031 (11)
C17	0.0965 (18)	0.0652 (15)	0.0556 (14)	−0.0038 (13)	−0.0093 (12)	0.0061 (11)
C18	0.0733 (14)	0.0555 (12)	0.0511 (12)	0.0024 (10)	−0.0042 (10)	0.0147 (10)
N1	0.0508 (9)	0.0488 (9)	0.0371 (8)	0.0020 (6)	0.0013 (6)	0.0165 (7)
N2	0.0566 (9)	0.0512 (9)	0.0410 (8)	0.0011 (7)	0.0000 (7)	0.0189 (7)
O1	0.0634 (9)	0.0770 (10)	0.0610 (9)	0.0117 (7)	−0.0025 (7)	0.0360 (8)

C1—N2	1.317 (2)	C9—C10	1.386 (3)
C1—N1	1.372 (2)	C9—H9	0.9300
C1—C13	1.467 (3)	C10—O1	1.358 (2)
C2—C3	1.356 (3)	C10—C11	1.380 (3)
C2—N2	1.368 (2)	C11—H11	0.9300
C2—C4	1.490 (3)	C12—O1	1.416 (3)
C3—N1	1.382 (2)	C12—H12A	0.9600
C3—C5	1.488 (3)	C12—H12B	0.9600
C4—H4A	0.9600	C12—H12C	0.9600
C4—H4B	0.9600	C13—C14	1.386 (3)
C4—H4C	0.9600	C13—C18	1.389 (3)
C5—H5A	0.9600	C14—C15	1.383 (3)
C5—H5B	0.9600	C14—H14	0.9300
C5—H5C	0.9600	C15—C16	1.373 (4)
C6—C7	1.380 (3)	C15—H15	0.9300
C6—C11	1.385 (2)	C16—C17	1.368 (4)
C6—N1	1.431 (2)	C16—H16	0.9300
C7—C8	1.380 (3)	C17—C18	1.377 (3)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.371 (3)	C18—H18	0.9300
C8—H8	0.9300
N2—C1—N1	110.51 (16)	O1—C10—C9	115.68 (17)
N2—C1—C13	122.63 (16)	C11—C10—C9	119.90 (17)
N1—C1—C13	126.73 (16)	C10—C11—C6	119.00 (17)
C3—C2—N2	110.20 (17)	C10—C11—H11	120.5
C3—C2—C4	128.78 (19)	C6—C11—H11	120.5
N2—C2—C4	121.02 (17)	O1—C12—H12A	109.5
C2—C3—N1	105.96 (16)	O1—C12—H12B	109.5
C2—C3—C5	130.95 (19)	H12A—C12—H12B	109.5
N1—C3—C5	123.08 (17)	O1—C12—H12C	109.5
C2—C4—H4A	109.5	H12A—C12—H12C	109.5
C2—C4—H4B	109.5	H12B—C12—H12C	109.5
H4A—C4—H4B	109.5	C14—C13—C18	117.98 (19)
C2—C4—H4C	109.5	C14—C13—C1	124.16 (18)
H4A—C4—H4C	109.5	C18—C13—C1	117.77 (17)
H4B—C4—H4C	109.5	C15—C14—C13	120.5 (2)
C3—C5—H5A	109.5	C15—C14—H14	119.7
C3—C5—H5B	109.5	C13—C14—H14	119.7
H5A—C5—H5B	109.5	C16—C15—C14	120.6 (2)
C3—C5—H5C	109.5	C16—C15—H15	119.7
H5A—C5—H5C	109.5	C14—C15—H15	119.7
H5B—C5—H5C	109.5	C17—C16—C15	119.3 (2)
C7—C6—C11	121.60 (17)	C17—C16—H16	120.3
C7—C6—N1	119.22 (16)	C15—C16—H16	120.3
C11—C6—N1	119.18 (16)	C16—C17—C18	120.6 (2)
C6—C7—C8	118.36 (18)	C16—C17—H17	119.7
C6—C7—H7	120.8	C18—C17—H17	119.7
C8—C7—H7	120.8	C17—C18—C13	120.9 (2)
C9—C8—C7	121.02 (19)	C17—C18—H18	119.5
C9—C8—H8	119.5	C13—C18—H18	119.5
C7—C8—H8	119.5	C1—N1—C3	106.80 (15)
C8—C9—C10	120.11 (18)	C1—N1—C6	127.92 (15)
C8—C9—H9	119.9	C3—N1—C6	124.33 (15)
C10—C9—H9	119.9	C1—N2—C2	106.53 (15)
O1—C10—C11	124.41 (18)	C10—O1—C12	117.98 (16)
N2—C2—C3—N1	−0.6 (2)	C15—C16—C17—C18	−0.4 (4)
C4—C2—C3—N1	178.6 (2)	C16—C17—C18—C13	1.3 (4)
N2—C2—C3—C5	−179.7 (2)	C14—C13—C18—C17	−1.1 (3)
C4—C2—C3—C5	−0.5 (4)	C1—C13—C18—C17	175.5 (2)
C11—C6—C7—C8	−1.0 (3)	N2—C1—N1—C3	0.2 (2)
N1—C6—C7—C8	179.48 (16)	C13—C1—N1—C3	176.15 (17)
C6—C7—C8—C9	1.0 (3)	N2—C1—N1—C6	169.31 (16)
C7—C8—C9—C10	0.1 (3)	C13—C1—N1—C6	−14.8 (3)
C8—C9—C10—O1	179.81 (17)	C2—C3—N1—C1	0.2 (2)
C8—C9—C10—C11	−1.2 (3)	C5—C3—N1—C1	179.5 (2)
O1—C10—C11—C6	−179.95 (16)	C2—C3—N1—C6	−169.35 (17)
C9—C10—C11—C6	1.1 (3)	C5—C3—N1—C6	9.9 (3)
C7—C6—C11—C10	0.0 (3)	C7—C6—N1—C1	−61.6 (2)
N1—C6—C11—C10	179.45 (15)	C11—C6—N1—C1	118.9 (2)
N2—C1—C13—C14	153.96 (19)	C7—C6—N1—C3	105.7 (2)
N1—C1—C13—C14	−21.5 (3)	C11—C6—N1—C3	−73.8 (2)
N2—C1—C13—C18	−22.4 (3)	N1—C1—N2—C2	−0.6 (2)
N1—C1—C13—C18	162.10 (19)	C13—C1—N2—C2	−176.70 (16)
C18—C13—C14—C15	0.1 (3)	C3—C2—N2—C1	0.7 (2)
C1—C13—C14—C15	−176.29 (19)	C4—C2—N2—C1	−178.6 (2)
C13—C14—C15—C16	0.7 (4)	C11—C10—O1—C12	5.4 (3)
C14—C15—C16—C17	−0.6 (4)	C9—C10—O1—C12	−175.63 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1i	0.96	2.57	3.316 (3)	135
C7—H7···N2ii	0.93	2.58	3.493 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1i	0.96	2.57	3.316 (3)	135
C7—H7⋯N2ii	0.93	2.58	3.493 (2)	168

Symmetry codes: (i) ; (ii) .