2-(3,4-Dimeth-oxy-phen-yl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole.

In the title compound, C(26)H(24)N(2)O(2), the planar 1H-imidazole ring makes dihedral angles of 35.78 (4), 26.35 (5) and 69.75 (5)°, respectively, with the dimeth-oxy-phenyl ring and the phenyl rings in the 4- and 5-positions. In the crystal, C-H⋯O hydrogen bonds connect neighbouring mol-ecules, forming infinite chains running along the b axis. Furthermore, the crystal structure exhibits a C-H-⋯π inter-action between a methyl H atom and a phenyl ring from an adjacent mol-ecule.

Related literature

For the synthesis of imidazole compounds, see: Shalini et al. (2010 ▶). For the medicinal properties of imidazole derivatives, see: Adams et al. (2001 ▶); Nakamura et al. (2004 ▶); Venkatesan et al. (2008 ▶); Nanterment et al. (2004 ▶); Roman et al. (2007 ▶); Congiu et al. (2008 ▶). For standard bond distances, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C26H24N2O2

M = 396.47

Triclinic,

a = 8.9683 (4) Å

b = 10.7916 (5) Å

c = 11.7219 (5) Å

α = 110.174 (2)°

β = 106.267 (2)°

γ = 91.991 (3)°

V = 1011.32 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 90 K

0.36 × 0.12 × 0.06 mm

Data collection

Bruker Kappa APEXII DUO diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.971, T max = 0.995

17346 measured reflections

6149 independent reflections

4408 reflections with I > 2σ(I)

R int = 0.039

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.127

S = 1.02

6149 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1983 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039566/bt6835sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039566/bt6835Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039566/bt6835Isup3.cml

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

C26H24N2O2	Z = 2
Mr = 396.47	F(000) = 420
Triclinic, P1	Dx = 1.302 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9683 (4) Å	Cell parameters from 3877 reflections
b = 10.7916 (5) Å	θ = 2.2–30.5°
c = 11.7219 (5) Å	µ = 0.08 mm−1
α = 110.174 (2)°	T = 90 K
β = 106.267 (2)°	Needle, colourless
γ = 91.991 (3)°	0.36 × 0.12 × 0.06 mm
V = 1011.32 (8) Å3

Bruker Kappa APEXII DUO diffractometer	6149 independent reflections
Radiation source: sealed tube	4408 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 30.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −12→12
Tmin = 0.971, Tmax = 0.995	k = −15→15
17346 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.309P] where P = (Fo2 + 2Fc2)/3
6149 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.25 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	0.60501 (12)	0.92104 (10)	0.24135 (9)	0.0174 (3)
O2	0.57242 (12)	0.86263 (10)	0.00369 (9)	0.0180 (3)
N1	0.72481 (13)	0.48753 (11)	0.32705 (10)	0.0136 (3)
N2	0.88572 (13)	0.40893 (11)	0.21328 (10)	0.0135 (3)
C1	0.70264 (16)	0.55194 (14)	0.03650 (12)	0.0160 (4)
C2	0.65044 (16)	0.64264 (14)	−0.02155 (12)	0.0163 (4)
C3	0.62078 (15)	0.76560 (13)	0.04910 (12)	0.0144 (3)
C4	0.63977 (16)	0.79788 (13)	0.18038 (12)	0.0141 (3)
C5	0.69306 (15)	0.70881 (13)	0.23773 (12)	0.0138 (3)
C6	0.72605 (15)	0.58461 (13)	0.16638 (12)	0.0134 (3)
C7	0.5608 (2)	0.83768 (15)	−0.12690 (13)	0.0229 (4)
C8	0.64201 (19)	0.96524 (14)	0.37715 (13)	0.0205 (4)
C9	0.77680 (15)	0.49333 (13)	0.23350 (12)	0.0129 (3)
C10	0.80286 (15)	0.39533 (13)	0.36895 (12)	0.0125 (3)
C11	0.90182 (15)	0.34498 (13)	0.29931 (12)	0.0129 (3)
C12	0.97719 (16)	0.39151 (14)	0.12516 (13)	0.0162 (4)
C13	0.91694 (18)	0.26993 (15)	0.00627 (13)	0.0207 (4)
C14	0.7876 (2)	0.18741 (17)	−0.02524 (15)	0.0277 (5)
C15	0.77327 (15)	0.36358 (12)	0.47378 (12)	0.0127 (3)
C16	0.62980 (16)	0.38237 (13)	0.49728 (12)	0.0146 (3)
C17	0.59989 (16)	0.36083 (14)	0.59963 (13)	0.0167 (4)
C18	0.71297 (17)	0.31669 (14)	0.67889 (13)	0.0172 (4)
C19	0.85580 (17)	0.29638 (14)	0.65568 (13)	0.0167 (4)
C20	0.88689 (16)	0.32016 (13)	0.55478 (12)	0.0150 (3)
C21	0.99892 (16)	0.23750 (13)	0.30191 (12)	0.0139 (3)
C22	0.92335 (17)	0.10790 (14)	0.26220 (14)	0.0180 (4)
C23	1.00989 (18)	0.00593 (14)	0.27258 (14)	0.0207 (4)
C24	1.17247 (17)	0.03201 (14)	0.32038 (13)	0.0181 (4)
C25	1.24860 (16)	0.16004 (14)	0.35776 (13)	0.0175 (4)
C26	1.16261 (16)	0.26308 (14)	0.34948 (13)	0.0162 (3)
H1	0.72180	0.46930	−0.01200	0.0190*
H2	0.63550	0.62000	−0.10840	0.0200*
H5	0.70730	0.73110	0.32450	0.0170*
H8A	0.57790	0.90890	0.39830	0.0310*
H8B	0.62230	1.05560	0.41010	0.0310*
H8C	0.75070	0.96090	0.41430	0.0310*
H9A	0.66190	0.82570	−0.13840	0.0340*
H9B	0.52540	0.91210	−0.14830	0.0340*
H9C	0.48740	0.75850	−0.18160	0.0340*
H12A	1.08480	0.38680	0.16900	0.0190*
H12B	0.97800	0.46930	0.10170	0.0190*
H13	0.97540	0.25080	−0.05030	0.0250*
H14A	0.72580	0.20300	0.02870	0.0330*
H14B	0.75810	0.11360	−0.10140	0.0330*
H16	0.55270	0.40990	0.44340	0.0170*
H17	0.50460	0.37590	0.61490	0.0200*
H18	0.69340	0.30080	0.74690	0.0210*
H19	0.93150	0.26650	0.70840	0.0200*
H20	0.98340	0.30720	0.54110	0.0180*
H22	0.81450	0.08960	0.22860	0.0220*
H23	0.95870	−0.08010	0.24740	0.0250*
H24	1.23020	−0.03640	0.32730	0.0220*
H25	1.35770	0.17720	0.38850	0.0210*
H26	1.21420	0.34920	0.37570	0.0190*

	U11	U22	U33	U12	U13	U23
O1	0.0249 (5)	0.0137 (5)	0.0147 (4)	0.0065 (4)	0.0063 (4)	0.0060 (4)
O2	0.0244 (5)	0.0182 (5)	0.0155 (4)	0.0069 (4)	0.0064 (4)	0.0108 (4)
N1	0.0149 (5)	0.0132 (5)	0.0146 (5)	0.0035 (4)	0.0050 (4)	0.0068 (4)
N2	0.0159 (5)	0.0133 (5)	0.0135 (5)	0.0036 (4)	0.0061 (4)	0.0064 (4)
C1	0.0183 (7)	0.0148 (6)	0.0152 (6)	0.0045 (5)	0.0061 (5)	0.0052 (5)
C2	0.0192 (7)	0.0179 (7)	0.0128 (6)	0.0030 (5)	0.0054 (5)	0.0064 (5)
C3	0.0138 (6)	0.0155 (6)	0.0155 (6)	0.0023 (5)	0.0034 (5)	0.0085 (5)
C4	0.0143 (6)	0.0132 (6)	0.0154 (6)	0.0022 (5)	0.0048 (5)	0.0057 (5)
C5	0.0146 (6)	0.0154 (6)	0.0126 (5)	0.0024 (5)	0.0039 (5)	0.0067 (5)
C6	0.0132 (6)	0.0140 (6)	0.0144 (6)	0.0024 (5)	0.0042 (5)	0.0069 (5)
C7	0.0328 (8)	0.0236 (8)	0.0159 (6)	0.0058 (6)	0.0071 (6)	0.0117 (6)
C8	0.0295 (8)	0.0180 (7)	0.0150 (6)	0.0078 (6)	0.0081 (6)	0.0058 (5)
C9	0.0130 (6)	0.0123 (6)	0.0130 (5)	0.0026 (5)	0.0035 (5)	0.0047 (5)
C10	0.0134 (6)	0.0113 (6)	0.0132 (5)	0.0024 (5)	0.0039 (5)	0.0050 (5)
C11	0.0144 (6)	0.0112 (6)	0.0133 (5)	0.0022 (5)	0.0043 (5)	0.0046 (5)
C12	0.0178 (6)	0.0171 (7)	0.0176 (6)	0.0054 (5)	0.0094 (5)	0.0078 (5)
C13	0.0272 (8)	0.0202 (7)	0.0177 (6)	0.0065 (6)	0.0123 (6)	0.0063 (6)
C14	0.0337 (9)	0.0261 (8)	0.0203 (7)	0.0011 (7)	0.0109 (7)	0.0032 (6)
C15	0.0153 (6)	0.0100 (6)	0.0128 (5)	0.0015 (5)	0.0047 (5)	0.0041 (5)
C16	0.0157 (6)	0.0138 (6)	0.0158 (6)	0.0043 (5)	0.0056 (5)	0.0067 (5)
C17	0.0171 (6)	0.0170 (7)	0.0184 (6)	0.0033 (5)	0.0086 (5)	0.0071 (5)
C18	0.0230 (7)	0.0157 (6)	0.0146 (6)	0.0016 (5)	0.0070 (5)	0.0069 (5)
C19	0.0197 (7)	0.0150 (6)	0.0150 (6)	0.0033 (5)	0.0030 (5)	0.0070 (5)
C20	0.0148 (6)	0.0145 (6)	0.0164 (6)	0.0038 (5)	0.0052 (5)	0.0060 (5)
C21	0.0168 (6)	0.0133 (6)	0.0134 (5)	0.0048 (5)	0.0064 (5)	0.0056 (5)
C22	0.0151 (6)	0.0157 (7)	0.0229 (7)	0.0029 (5)	0.0051 (5)	0.0072 (6)
C23	0.0237 (7)	0.0124 (6)	0.0264 (7)	0.0040 (6)	0.0082 (6)	0.0073 (6)
C24	0.0219 (7)	0.0167 (7)	0.0187 (6)	0.0097 (6)	0.0084 (5)	0.0079 (5)
C25	0.0143 (6)	0.0200 (7)	0.0188 (6)	0.0053 (5)	0.0045 (5)	0.0083 (6)
C26	0.0170 (6)	0.0134 (6)	0.0175 (6)	0.0022 (5)	0.0053 (5)	0.0051 (5)

O1—C4	1.3685 (18)	C22—C23	1.388 (2)
O1—C8	1.4286 (17)	C23—C24	1.387 (2)
O2—C3	1.3618 (18)	C24—C25	1.384 (2)
O2—C7	1.4321 (17)	C25—C26	1.390 (2)
N1—C9	1.3250 (18)	C1—H1	0.9300
N1—C10	1.3835 (19)	C2—H2	0.9300
N2—C9	1.3721 (19)	C5—H5	0.9300
N2—C11	1.3854 (18)	C7—H9A	0.9600
N2—C12	1.4583 (18)	C7—H9B	0.9600
C1—C2	1.398 (2)	C7—H9C	0.9600
C1—C6	1.3899 (18)	C8—H8A	0.9600
C2—C3	1.381 (2)	C8—H8B	0.9600
C3—C4	1.4134 (18)	C8—H8C	0.9600
C4—C5	1.379 (2)	C12—H12A	0.9700
C5—C6	1.406 (2)	C12—H12B	0.9700
C6—C9	1.470 (2)	C13—H13	0.9300
C10—C11	1.3721 (19)	C14—H14A	0.9300
C10—C15	1.4712 (19)	C14—H14B	0.9300
C11—C21	1.478 (2)	C16—H16	0.9300
C12—C13	1.491 (2)	C17—H17	0.9300
C13—C14	1.318 (3)	C18—H18	0.9300
C15—C16	1.397 (2)	C19—H19	0.9300
C15—C20	1.3991 (19)	C20—H20	0.9300
C16—C17	1.391 (2)	C22—H22	0.9300
C17—C18	1.389 (2)	C23—H23	0.9300
C18—C19	1.392 (2)	C24—H24	0.9300
C19—C20	1.390 (2)	C25—H25	0.9300
C21—C22	1.393 (2)	C26—H26	0.9300
C21—C26	1.396 (2)
C4—O1—C8	116.86 (11)	C1—C2—H2	120.00
C3—O2—C7	116.81 (12)	C3—C2—H2	120.00
C9—N1—C10	105.70 (12)	C4—C5—H5	120.00
C9—N2—C11	106.90 (11)	C6—C5—H5	120.00
C9—N2—C12	128.55 (12)	O2—C7—H9A	109.00
C11—N2—C12	124.46 (12)	O2—C7—H9B	109.00
C2—C1—C6	120.37 (13)	O2—C7—H9C	110.00
C1—C2—C3	120.52 (12)	H9A—C7—H9B	109.00
O2—C3—C2	125.76 (12)	H9A—C7—H9C	109.00
O2—C3—C4	114.84 (12)	H9B—C7—H9C	109.00
C2—C3—C4	119.40 (13)	O1—C8—H8A	109.00
O1—C4—C3	114.91 (12)	O1—C8—H8B	109.00
O1—C4—C5	125.16 (12)	O1—C8—H8C	109.00
C3—C4—C5	119.92 (13)	H8A—C8—H8B	110.00
C4—C5—C6	120.68 (12)	H8A—C8—H8C	109.00
C1—C6—C5	119.06 (13)	H8B—C8—H8C	109.00
C1—C6—C9	123.53 (13)	N2—C12—H12A	109.00
C5—C6—C9	117.34 (11)	N2—C12—H12B	109.00
N1—C9—N2	111.38 (12)	C13—C12—H12A	109.00
N1—C9—C6	122.61 (13)	C13—C12—H12B	109.00
N2—C9—C6	125.96 (12)	H12A—C12—H12B	108.00
N1—C10—C11	110.18 (12)	C12—C13—H13	117.00
N1—C10—C15	120.50 (12)	C14—C13—H13	117.00
C11—C10—C15	129.32 (13)	C13—C14—H14A	120.00
N2—C11—C10	105.85 (12)	C13—C14—H14B	120.00
N2—C11—C21	124.07 (12)	H14A—C14—H14B	120.00
C10—C11—C21	129.91 (13)	C15—C16—H16	119.00
N2—C12—C13	113.96 (13)	C17—C16—H16	119.00
C12—C13—C14	125.34 (15)	C16—C17—H17	120.00
C10—C15—C16	119.34 (12)	C18—C17—H17	120.00
C10—C15—C20	122.15 (13)	C17—C18—H18	120.00
C16—C15—C20	118.45 (12)	C19—C18—H18	120.00
C15—C16—C17	121.38 (13)	C18—C19—H19	120.00
C16—C17—C18	119.72 (14)	C20—C19—H19	120.00
C17—C18—C19	119.41 (13)	C15—C20—H20	120.00
C18—C19—C20	120.92 (14)	C19—C20—H20	120.00
C15—C20—C19	120.11 (14)	C21—C22—H22	120.00
C11—C21—C22	118.45 (13)	C23—C22—H22	120.00
C11—C21—C26	122.14 (13)	C22—C23—H23	120.00
C22—C21—C26	119.31 (14)	C24—C23—H23	120.00
C21—C22—C23	120.26 (14)	C23—C24—H24	120.00
C22—C23—C24	120.17 (15)	C25—C24—H24	120.00
C23—C24—C25	119.91 (15)	C24—C25—H25	120.00
C24—C25—C26	120.24 (14)	C26—C25—H25	120.00
C21—C26—C25	120.08 (14)	C21—C26—H26	120.00
C2—C1—H1	120.00	C25—C26—H26	120.00
C6—C1—H1	120.00
C8—O1—C4—C3	−171.98 (13)	C5—C6—C9—N2	−143.78 (14)
C8—O1—C4—C5	6.6 (2)	C1—C6—C9—N1	−143.64 (15)
C7—O2—C3—C4	176.30 (13)	C5—C6—C9—N1	33.3 (2)
C7—O2—C3—C2	−4.1 (2)	N1—C10—C11—N2	0.70 (15)
C10—N1—C9—N2	−0.18 (15)	C11—C10—C15—C20	28.2 (2)
C9—N1—C10—C11	−0.34 (15)	N1—C10—C15—C20	−152.15 (13)
C10—N1—C9—C6	−177.67 (12)	C11—C10—C15—C16	−154.50 (15)
C9—N1—C10—C15	179.97 (11)	C15—C10—C11—C21	5.1 (2)
C12—N2—C11—C21	−8.3 (2)	N1—C10—C15—C16	25.13 (19)
C11—N2—C9—C6	178.00 (13)	N1—C10—C11—C21	−174.60 (13)
C9—N2—C11—C21	174.87 (13)	C15—C10—C11—N2	−179.65 (13)
C12—N2—C11—C10	176.06 (12)	N2—C11—C21—C22	−109.09 (16)
C11—N2—C9—N1	0.61 (15)	C10—C11—C21—C26	−110.82 (18)
C12—N2—C9—N1	−176.05 (13)	N2—C11—C21—C26	74.64 (18)
C11—N2—C12—C13	81.73 (17)	C10—C11—C21—C22	65.5 (2)
C9—N2—C12—C13	−102.15 (17)	N2—C12—C13—C14	4.5 (2)
C9—N2—C11—C10	−0.78 (15)	C10—C15—C16—C17	−176.38 (13)
C12—N2—C9—C6	1.3 (2)	C20—C15—C16—C17	1.0 (2)
C2—C1—C6—C9	178.37 (14)	C10—C15—C20—C19	177.46 (13)
C2—C1—C6—C5	1.4 (2)	C16—C15—C20—C19	0.2 (2)
C6—C1—C2—C3	−0.3 (2)	C15—C16—C17—C18	−1.5 (2)
C1—C2—C3—C4	−1.6 (2)	C16—C17—C18—C19	0.9 (2)
C1—C2—C3—O2	178.77 (14)	C17—C18—C19—C20	0.3 (2)
C2—C3—C4—C5	2.4 (2)	C18—C19—C20—C15	−0.8 (2)
O2—C3—C4—O1	0.68 (19)	C11—C21—C22—C23	−174.93 (13)
O2—C3—C4—C5	−177.97 (13)	C26—C21—C22—C23	1.5 (2)
C2—C3—C4—O1	−178.96 (13)	C11—C21—C26—C25	175.78 (13)
C3—C4—C5—C6	−1.2 (2)	C22—C21—C26—C25	−0.5 (2)
O1—C4—C5—C6	−179.74 (13)	C21—C22—C23—C24	−1.2 (2)
C4—C5—C6—C1	−0.7 (2)	C22—C23—C24—C25	0.0 (2)
C4—C5—C6—C9	−177.80 (13)	C23—C24—C25—C26	1.0 (2)
C1—C6—C9—N2	39.2 (2)	C24—C25—C26—C21	−0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H9B···O1i	0.96	2.57	3.515 (2)	170
C14—H14A···N2	0.93	2.53	2.859 (2)	101
C8—H8B···Cg3ii	0.96	2.98	3.8316 (17)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C15–C20 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H9B⋯O1i	0.96	2.57	3.515 (2)	170
C8—H8B⋯Cg3ii	0.96	2.98	3.8316 (17)	149

Symmetry codes: (i) ; (ii) .