2-(2,5-Di-meth-oxy-phen-yl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole.

In the title compound, C26H24N2O2, the two phenyl and the 2,5-di-meth-oxy-phen-yl rings are inclined to the imidazole ring at dihedral angles of 30.38 (8), 56.59 (9) and 73.11 (9)°, respectively. In the crystal, mol-ecules are linked by pairs of C-H⋯O inter-actions into centrosymmetric dimers with graph-set notation R 2 (2)(8). C-H⋯π inter-actions are also observed.

Related literature

For chemical properties and applications of imidazoles with an unsaturated side chain, see, for example: Koszykowska et al. (2009 ▶); Berezin et al. (2009 ▶); Rambo et al. (2010 ▶); Min et al. (2006 ▶). For similar structures, see: Akkurt et al. (2013a ▶,b ▶); Mohamed et al. (2013a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H24N2O2

M = 396.47

Triclinic,

a = 8.3117 (14) Å

b = 10.5217 (17) Å

c = 13.425 (2) Å

α = 105.938 (2)°

β = 101.846 (2)°

γ = 107.772 (2)°

V = 1020.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.26 × 0.16 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.979, T max = 0.993

11527 measured reflections

4193 independent reflections

3184 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.125

S = 1.05

4193 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813015936/bx2444sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015936/bx2444Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015936/bx2444Isup3.cml

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

C26H24N2O2	Z = 2
Mr = 396.47	F(000) = 420
Triclinic, P1	Dx = 1.291 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3117 (14) Å	Cell parameters from 2470 reflections
b = 10.5217 (17) Å	θ = 2.2–26.3°
c = 13.425 (2) Å	µ = 0.08 mm−1
α = 105.938 (2)°	T = 100 K
β = 101.846 (2)°	Prism, colourless
γ = 107.772 (2)°	0.26 × 0.16 × 0.08 mm
V = 1020.1 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	4193 independent reflections
Radiation source: sealed tube	3184 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
phi and ω scans	θmax = 26.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.979, Tmax = 0.993	k = −13→13
11527 measured reflections	l = −16→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0613P)2 + 0.1427P] where P = (Fo2 + 2Fc2)/3
4193 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1	0.22127 (15)	0.57663 (13)	−0.01565 (9)	0.0294 (4)
O2	0.51365 (14)	0.51988 (12)	0.37054 (9)	0.0246 (3)
N1	0.03320 (16)	0.34760 (14)	0.28257 (10)	0.0200 (4)
N2	0.19265 (16)	0.21885 (14)	0.23560 (10)	0.0197 (4)
C1	0.1675 (2)	0.34409 (16)	0.24524 (12)	0.0187 (4)
C2	0.0647 (2)	0.13719 (17)	0.26932 (12)	0.0191 (5)
C3	−0.0325 (2)	0.21832 (16)	0.29722 (12)	0.0187 (5)
C4	−0.1839 (2)	0.18601 (17)	0.34015 (12)	0.0196 (5)
C5	−0.2095 (2)	0.29766 (17)	0.41145 (13)	0.0221 (5)
C6	−0.3463 (2)	0.26861 (19)	0.45693 (13)	0.0244 (5)
C7	−0.4602 (2)	0.12872 (19)	0.43134 (14)	0.0257 (5)
C8	−0.4395 (2)	0.01733 (19)	0.35825 (14)	0.0253 (5)
C9	−0.3029 (2)	0.04563 (17)	0.31312 (13)	0.0219 (5)
C10	0.05668 (19)	−0.00280 (17)	0.27544 (13)	0.0194 (4)
C11	0.0409 (2)	−0.11491 (17)	0.18480 (13)	0.0234 (5)
C12	0.0405 (2)	−0.24371 (18)	0.19320 (14)	0.0264 (5)
C13	0.0564 (2)	−0.26260 (18)	0.29232 (14)	0.0248 (5)
C14	0.0700 (2)	−0.15270 (17)	0.38256 (13)	0.0228 (5)
C15	0.0696 (2)	−0.02425 (17)	0.37420 (13)	0.0210 (5)
C16	0.3286 (2)	0.18032 (18)	0.19444 (13)	0.0229 (5)
C17	0.2732 (2)	0.12340 (19)	0.07169 (14)	0.0280 (5)
C18	0.2775 (3)	0.0033 (2)	0.01278 (16)	0.0392 (7)
C19	0.2772 (2)	0.45508 (16)	0.21242 (13)	0.0199 (5)
C20	0.2057 (2)	0.47090 (17)	0.11627 (13)	0.0221 (5)
C21	0.3087 (2)	0.56926 (17)	0.08016 (13)	0.0220 (5)
C22	0.4852 (2)	0.65115 (17)	0.14076 (14)	0.0238 (5)
C23	0.5580 (2)	0.63844 (17)	0.23932 (13)	0.0233 (5)
C24	0.4555 (2)	0.54150 (16)	0.27547 (13)	0.0202 (5)
C25	0.6880 (2)	0.61529 (18)	0.44233 (14)	0.0292 (5)
C26	0.3278 (2)	0.64720 (19)	−0.07022 (15)	0.0303 (6)
H5	−0.13280	0.39400	0.42890	0.0270*
H6	−0.36170	0.34510	0.50580	0.0290*
H7	−0.55200	0.10910	0.46370	0.0310*
H8	−0.51920	−0.07860	0.33910	0.0300*
H9	−0.28980	−0.03130	0.26320	0.0260*
H11	0.03020	−0.10310	0.11640	0.0280*
H12	0.02920	−0.31920	0.13060	0.0320*
H13	0.05790	−0.35020	0.29830	0.0300*
H14	0.07970	−0.16520	0.45070	0.0270*
H15	0.07820	0.05010	0.43670	0.0250*
H16A	0.35140	0.10690	0.22150	0.0270*
H16B	0.44100	0.26590	0.22340	0.0270*
H17	0.23240	0.17810	0.03450	0.0340*
H18A	0.31760	−0.05390	0.04740	0.0470*
H18B	0.24060	−0.02650	−0.06460	0.0470*
H20	0.08470	0.41400	0.07420	0.0270*
H22	0.55700	0.71610	0.11540	0.0290*
H23	0.67860	0.69670	0.28170	0.0280*
H25A	0.77680	0.59950	0.40780	0.0440*
H25B	0.70890	0.59740	0.51080	0.0440*
H25C	0.69790	0.71440	0.45760	0.0440*
H26A	0.39130	0.74890	−0.02480	0.0450*
H26B	0.25120	0.63740	−0.14020	0.0450*
H26C	0.41400	0.60380	−0.08310	0.0450*

	U11	U22	U33	U12	U13	U23
O1	0.0266 (6)	0.0360 (7)	0.0281 (7)	0.0075 (5)	0.0080 (5)	0.0209 (6)
O2	0.0216 (6)	0.0252 (6)	0.0223 (6)	0.0044 (5)	0.0028 (5)	0.0098 (5)
N1	0.0190 (7)	0.0203 (7)	0.0193 (7)	0.0059 (6)	0.0055 (6)	0.0074 (6)
N2	0.0188 (7)	0.0205 (7)	0.0210 (7)	0.0079 (6)	0.0073 (6)	0.0080 (6)
C1	0.0183 (7)	0.0192 (8)	0.0169 (8)	0.0064 (6)	0.0042 (6)	0.0059 (7)
C2	0.0181 (8)	0.0204 (8)	0.0156 (8)	0.0047 (7)	0.0040 (6)	0.0060 (7)
C3	0.0189 (8)	0.0187 (8)	0.0167 (8)	0.0058 (6)	0.0046 (6)	0.0062 (6)
C4	0.0189 (8)	0.0233 (9)	0.0193 (8)	0.0092 (7)	0.0060 (6)	0.0106 (7)
C5	0.0215 (8)	0.0219 (9)	0.0253 (9)	0.0090 (7)	0.0080 (7)	0.0108 (7)
C6	0.0245 (8)	0.0308 (9)	0.0249 (9)	0.0160 (8)	0.0102 (7)	0.0125 (8)
C7	0.0202 (8)	0.0357 (10)	0.0300 (9)	0.0133 (8)	0.0119 (7)	0.0189 (8)
C8	0.0177 (8)	0.0282 (9)	0.0298 (9)	0.0054 (7)	0.0051 (7)	0.0159 (8)
C9	0.0202 (8)	0.0221 (9)	0.0226 (9)	0.0078 (7)	0.0050 (7)	0.0086 (7)
C10	0.0152 (7)	0.0200 (8)	0.0215 (8)	0.0058 (6)	0.0044 (6)	0.0073 (7)
C11	0.0237 (8)	0.0248 (9)	0.0213 (9)	0.0090 (7)	0.0068 (7)	0.0085 (7)
C12	0.0296 (9)	0.0217 (9)	0.0248 (9)	0.0100 (7)	0.0080 (7)	0.0043 (7)
C13	0.0241 (8)	0.0206 (9)	0.0326 (10)	0.0099 (7)	0.0093 (7)	0.0123 (8)
C14	0.0205 (8)	0.0256 (9)	0.0236 (9)	0.0073 (7)	0.0077 (7)	0.0121 (7)
C15	0.0180 (8)	0.0216 (9)	0.0226 (8)	0.0068 (7)	0.0069 (7)	0.0072 (7)
C16	0.0194 (8)	0.0249 (9)	0.0260 (9)	0.0093 (7)	0.0084 (7)	0.0096 (7)
C17	0.0249 (9)	0.0345 (10)	0.0263 (9)	0.0113 (8)	0.0113 (7)	0.0114 (8)
C18	0.0452 (12)	0.0426 (12)	0.0293 (10)	0.0187 (10)	0.0155 (9)	0.0073 (9)
C19	0.0194 (8)	0.0190 (8)	0.0224 (8)	0.0073 (7)	0.0100 (7)	0.0067 (7)
C20	0.0197 (8)	0.0213 (8)	0.0234 (9)	0.0056 (7)	0.0057 (7)	0.0088 (7)
C21	0.0243 (8)	0.0246 (9)	0.0202 (8)	0.0111 (7)	0.0073 (7)	0.0104 (7)
C22	0.0253 (8)	0.0201 (8)	0.0293 (9)	0.0078 (7)	0.0132 (7)	0.0115 (7)
C23	0.0206 (8)	0.0222 (9)	0.0249 (9)	0.0062 (7)	0.0069 (7)	0.0077 (7)
C24	0.0214 (8)	0.0198 (8)	0.0201 (8)	0.0092 (7)	0.0070 (7)	0.0063 (7)
C25	0.0243 (9)	0.0263 (9)	0.0281 (9)	0.0045 (8)	−0.0003 (7)	0.0087 (8)
C26	0.0363 (10)	0.0328 (10)	0.0315 (10)	0.0149 (8)	0.0173 (8)	0.0193 (8)

O1—C21	1.376 (2)	C20—C21	1.394 (3)
O1—C26	1.427 (2)	C21—C22	1.382 (2)
O2—C24	1.374 (2)	C22—C23	1.397 (2)
O2—C25	1.430 (2)	C23—C24	1.383 (2)
N1—C1	1.320 (2)	C5—H5	0.9500
N1—C3	1.387 (2)	C6—H6	0.9500
N2—C1	1.372 (2)	C7—H7	0.9500
N2—C2	1.388 (2)	C8—H8	0.9500
N2—C16	1.470 (2)	C9—H9	0.9500
C1—C19	1.479 (2)	C11—H11	0.9500
C2—C3	1.375 (2)	C12—H12	0.9500
C2—C10	1.480 (3)	C13—H13	0.9500
C3—C4	1.475 (2)	C14—H14	0.9500
C4—C5	1.400 (2)	C15—H15	0.9500
C4—C9	1.399 (3)	C16—H16A	0.9900
C5—C6	1.391 (3)	C16—H16B	0.9900
C6—C7	1.385 (3)	C17—H17	0.9500
C7—C8	1.388 (3)	C18—H18A	0.9500
C8—C9	1.386 (3)	C18—H18B	0.9500
C10—C11	1.393 (2)	C20—H20	0.9500
C10—C15	1.393 (2)	C22—H22	0.9500
C11—C12	1.390 (3)	C23—H23	0.9500
C12—C13	1.385 (3)	C25—H25A	0.9800
C13—C14	1.383 (2)	C25—H25B	0.9800
C14—C15	1.388 (3)	C25—H25C	0.9800
C16—C17	1.505 (2)	C26—H26A	0.9800
C17—C18	1.309 (3)	C26—H26B	0.9800
C19—C20	1.382 (2)	C26—H26C	0.9800
C19—C24	1.407 (2)
C21—O1—C26	117.36 (14)	C5—C6—H6	120.00
C24—O2—C25	116.87 (14)	C7—C6—H6	120.00
C1—N1—C3	105.42 (14)	C6—C7—H7	120.00
C1—N2—C2	107.22 (14)	C8—C7—H7	120.00
C1—N2—C16	125.18 (15)	C7—C8—H8	120.00
C2—N2—C16	127.58 (15)	C9—C8—H8	120.00
N1—C1—N2	111.60 (15)	C4—C9—H9	120.00
N1—C1—C19	126.41 (16)	C8—C9—H9	120.00
N2—C1—C19	121.96 (15)	C10—C11—H11	120.00
N2—C2—C3	105.17 (15)	C12—C11—H11	120.00
N2—C2—C10	122.53 (15)	C11—C12—H12	120.00
C3—C2—C10	132.23 (16)	C13—C12—H12	120.00
N1—C3—C2	110.59 (15)	C12—C13—H13	120.00
N1—C3—C4	120.32 (15)	C14—C13—H13	120.00
C2—C3—C4	129.08 (16)	C13—C14—H14	120.00
C3—C4—C5	119.76 (16)	C15—C14—H14	120.00
C3—C4—C9	121.91 (15)	C10—C15—H15	120.00
C5—C4—C9	118.32 (16)	C14—C15—H15	120.00
C4—C5—C6	120.51 (17)	N2—C16—H16A	109.00
C5—C6—C7	120.36 (16)	N2—C16—H16B	109.00
C6—C7—C8	119.68 (17)	C17—C16—H16A	109.00
C7—C8—C9	120.17 (18)	C17—C16—H16B	109.00
C4—C9—C8	120.90 (16)	H16A—C16—H16B	108.00
C2—C10—C11	121.70 (15)	C16—C17—H17	118.00
C2—C10—C15	120.15 (15)	C18—C17—H17	118.00
C11—C10—C15	118.13 (16)	C17—C18—H18A	120.00
C10—C11—C12	120.84 (16)	C17—C18—H18B	120.00
C11—C12—C13	120.37 (16)	H18A—C18—H18B	120.00
C12—C13—C14	119.31 (17)	C19—C20—H20	120.00
C13—C14—C15	120.39 (16)	C21—C20—H20	120.00
C10—C15—C14	120.96 (15)	C21—C22—H22	120.00
N2—C16—C17	112.28 (14)	C23—C22—H22	120.00
C16—C17—C18	124.22 (18)	C22—C23—H23	120.00
C1—C19—C20	119.57 (15)	C24—C23—H23	120.00
C1—C19—C24	121.05 (15)	O2—C25—H25A	109.00
C20—C19—C24	119.34 (16)	O2—C25—H25B	109.00
C19—C20—C21	120.92 (16)	O2—C25—H25C	109.00
O1—C21—C20	115.32 (15)	H25A—C25—H25B	109.00
O1—C21—C22	125.10 (16)	H25A—C25—H25C	109.00
C20—C21—C22	119.58 (16)	H25B—C25—H25C	109.00
C21—C22—C23	120.05 (16)	O1—C26—H26A	109.00
C22—C23—C24	120.34 (16)	O1—C26—H26B	109.00
O2—C24—C19	115.12 (15)	O1—C26—H26C	109.00
O2—C24—C23	125.15 (15)	H26A—C26—H26B	109.00
C19—C24—C23	119.74 (15)	H26A—C26—H26C	109.00
C4—C5—H5	120.00	H26B—C26—H26C	109.00
C6—C5—H5	120.00
C26—O1—C21—C22	15.8 (2)	C2—C3—C4—C5	148.45 (17)
C26—O1—C21—C20	−164.74 (15)	N1—C3—C4—C5	−29.8 (2)
C25—O2—C24—C19	−173.84 (15)	C3—C4—C5—C6	−176.81 (15)
C25—O2—C24—C23	6.6 (2)	C3—C4—C9—C8	177.09 (16)
C1—N1—C3—C2	0.58 (17)	C9—C4—C5—C6	2.2 (2)
C1—N1—C3—C4	179.16 (14)	C5—C4—C9—C8	−1.9 (2)
C3—N1—C1—N2	−0.36 (17)	C4—C5—C6—C7	−0.7 (3)
C3—N1—C1—C19	177.32 (15)	C5—C6—C7—C8	−1.3 (3)
C16—N2—C1—C19	0.9 (2)	C6—C7—C8—C9	1.6 (3)
C16—N2—C2—C10	4.5 (2)	C7—C8—C9—C4	0.0 (3)
C2—N2—C1—C19	−177.79 (14)	C2—C10—C11—C12	177.49 (17)
C16—N2—C2—C3	−178.34 (14)	C11—C10—C15—C14	1.2 (3)
C1—N2—C2—C10	−176.80 (14)	C2—C10—C15—C14	−177.22 (16)
C16—N2—C1—N1	178.73 (13)	C15—C10—C11—C12	−0.9 (3)
C2—N2—C16—C17	97.69 (19)	C10—C11—C12—C13	−0.2 (3)
C1—N2—C16—C17	−80.8 (2)	C11—C12—C13—C14	1.0 (3)
C2—N2—C1—N1	0.00 (17)	C12—C13—C14—C15	−0.7 (3)
C1—N2—C2—C3	0.34 (16)	C13—C14—C15—C10	−0.4 (3)
N1—C1—C19—C20	−72.9 (2)	N2—C16—C17—C18	−129.1 (2)
N1—C1—C19—C24	109.5 (2)	C1—C19—C24—C23	176.09 (16)
N2—C1—C19—C20	104.59 (19)	C20—C19—C24—O2	178.86 (15)
N2—C1—C19—C24	−73.1 (2)	C1—C19—C24—O2	−3.5 (2)
N2—C2—C10—C15	121.30 (18)	C24—C19—C20—C21	1.2 (3)
C3—C2—C10—C11	126.7 (2)	C20—C19—C24—C23	−1.6 (3)
C3—C2—C10—C15	−55.0 (3)	C1—C19—C20—C21	−176.52 (16)
N2—C2—C10—C11	−57.0 (2)	C19—C20—C21—C22	0.6 (3)
N2—C2—C3—C4	−178.98 (15)	C19—C20—C21—O1	−178.89 (16)
N2—C2—C3—N1	−0.57 (17)	C20—C21—C22—C23	−2.0 (3)
C10—C2—C3—N1	176.17 (16)	O1—C21—C22—C23	177.44 (16)
C10—C2—C3—C4	−2.3 (3)	C21—C22—C23—C24	1.6 (3)
C2—C3—C4—C9	−30.5 (3)	C22—C23—C24—C19	0.2 (3)
N1—C3—C4—C9	151.19 (15)	C22—C23—C24—O2	179.71 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O1i	0.95	2.54	3.354 (2)	143
C14—H14···Cg2ii	0.95	2.63	3.4083 (19)	139
C25—H25B···Cg1iii	0.98	2.84	3.6337 (19)	139
C26—H26C···Cg4iv	0.98	2.95	3.908 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the N1/N2/C1–C3, C4–C9 and C19–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O1i	0.95	2.54	3.354 (2)	143
C14—H14⋯Cg2ii	0.95	2.63	3.4083 (19)	139
C25—H25B⋯Cg1iii	0.98	2.84	3.6337 (19)	139
C26—H26C⋯Cg4iv	0.98	2.95	3.908 (2)	166

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