2-(4-Bromo-phen-yl)-1-pentyl-4,5-diphenyl-1H-imidazole.

The title compound, C26H25BrN2, is isomorphous with the chloro derivative [2-(4-chloro-phen-yl)-1-pentyl-4,5-diphenyl-1H-imidazole; Mohamed et al. (2013 ▶). Acta Cryst. E69, o846-o847]. The two phenyl rings and the 4-bromo-phenyl ring are oriented at dihedral angles of 30.1 (2), 64.3 (3) and 42.0 (2)°, respectively, with respect to the imidazole ring. In the crystal, mol-ecules stack in columns along the b-axis direction, however, there are no significant inter-molecular inter-actions present.

Related literature

For biological and synthetic applications of imidazole deriv­atives, see: Maier et al. (1989a ▶,b ▶); Welton (1999 ▶); Hermann & Kocher (1997 ▶). For related structures, see: Akkurt et al. (2013 ▶); Mohamed et al. (2013 ▶); Simpson et al. (2013 ▶).

Experimental

Crystal data

C26H25BrN2

M = 445.39

Monoclinic,

a = 10.665 (5) Å

b = 9.619 (5) Å

c = 21.541 (10) Å

β = 91.092 (9)°

V = 2209.4 (19) Å3

Z = 4

Mo Kα radiation

μ = 1.88 mm−1

T = 150 K

0.36 × 0.16 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.600, T max = 0.969

16966 measured reflections

4329 independent reflections

2328 reflections with I > 2σ(I)

R int = 0.187

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.116

S = 0.88

4329 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −1.05 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); 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/S1600536813021983/su2633sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021983/su2633Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021983/su2633Isup3.cml

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

C26H25BrN2	F(000) = 920
Mr = 445.39	Dx = 1.339 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 638 reflections
a = 10.665 (5) Å	θ = 2.3–23.5°
b = 9.619 (5) Å	µ = 1.88 mm−1
c = 21.541 (10) Å	T = 150 K
β = 91.092 (9)°	Plate, colourless
V = 2209.4 (19) Å3	0.36 × 0.16 × 0.03 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4329 independent reflections
Radiation source: fine-focus sealed tube	2328 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.187
φ and ο scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −13→13
Tmin = 0.600, Tmax = 0.969	k = −11→11
16966 measured reflections	l = −25→26

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 0.88	w = 1/[σ2(Fo2) + (0.0277P)2] where P = (Fo2 + 2Fc2)/3
4329 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −1.05 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
Br1	0.48280 (5)	1.06999 (7)	1.12186 (2)	0.0518 (2)
N1	0.9579 (3)	0.7532 (4)	0.95097 (14)	0.0260 (14)
N2	1.0328 (3)	0.7435 (4)	1.04691 (14)	0.0291 (14)
C1	0.9420 (4)	0.7928 (5)	1.01128 (18)	0.0266 (14)
C2	1.1118 (4)	0.6715 (5)	1.00900 (18)	0.0266 (14)
C3	1.0659 (4)	0.6773 (5)	0.94893 (18)	0.0289 (14)
C4	0.8327 (4)	0.8632 (5)	1.03554 (18)	0.0287 (14)
C5	0.7751 (4)	0.9785 (5)	1.00753 (18)	0.0330 (18)
C6	0.6714 (4)	1.0384 (5)	1.03236 (18)	0.0331 (18)
C7	0.6244 (4)	0.9856 (5)	1.08588 (19)	0.0340 (18)
C8	0.6802 (4)	0.8754 (6)	1.11597 (19)	0.0356 (18)
C9	0.7843 (4)	0.8143 (5)	1.09045 (18)	0.0290 (16)
C10	1.2222 (4)	0.6036 (5)	1.03414 (18)	0.0286 (16)
C11	1.2824 (4)	0.6578 (5)	1.0867 (2)	0.0403 (19)
C12	1.3866 (5)	0.5930 (7)	1.1121 (2)	0.054 (2)
C13	1.4331 (5)	0.4747 (6)	1.0864 (2)	0.053 (2)
C14	1.3738 (4)	0.4185 (6)	1.0344 (2)	0.0462 (19)
C15	1.2697 (4)	0.4841 (5)	1.00872 (19)	0.0344 (18)
C16	1.1136 (4)	0.6206 (5)	0.89021 (18)	0.0287 (16)
C17	1.2266 (4)	0.6687 (6)	0.8681 (2)	0.0426 (19)
C18	1.2736 (5)	0.6162 (6)	0.8134 (2)	0.053 (2)
C19	1.2084 (5)	0.5199 (6)	0.7801 (2)	0.048 (2)
C20	1.0959 (5)	0.4708 (6)	0.80118 (19)	0.047 (2)
C21	1.0490 (5)	0.5224 (5)	0.85652 (18)	0.0366 (16)
C22	0.8836 (4)	0.7999 (5)	0.89621 (18)	0.0304 (16)
C23	0.9433 (4)	0.9208 (5)	0.86564 (18)	0.0313 (14)
C24	0.8586 (4)	0.9869 (5)	0.81709 (19)	0.0360 (18)
C25	0.9148 (4)	1.1120 (6)	0.7870 (2)	0.048 (2)
C26	0.8257 (5)	1.1835 (6)	0.7416 (2)	0.064 (2)
H5	0.80860	1.01570	0.97050	0.0400*
H6	0.63250	1.11590	1.01260	0.0400*
H8	0.64750	0.84160	1.15380	0.0430*
H9	0.82320	0.73770	1.11090	0.0350*
H11	1.25130	0.74020	1.10520	0.0480*
H12	1.42660	0.63130	1.14800	0.0640*
H13	1.50530	0.43110	1.10410	0.0640*
H14	1.40460	0.33530	1.01640	0.0560*
H15	1.23010	0.44580	0.97270	0.0410*
H17	1.27200	0.73790	0.89040	0.0510*
H18	1.35230	0.64800	0.79910	0.0630*
H19	1.24060	0.48620	0.74210	0.0580*
H20	1.05050	0.40230	0.77820	0.0560*
H21	0.97110	0.48900	0.87110	0.0440*
H22A	0.79830	0.82590	0.90930	0.0360*
H22B	0.87570	0.72240	0.86610	0.0360*
H23A	1.02160	0.88990	0.84590	0.0380*
H23B	0.96580	0.99100	0.89750	0.0380*
H24A	0.83830	0.91710	0.78460	0.0430*
H24B	0.77900	1.01430	0.83670	0.0430*
H25A	0.99110	1.08340	0.76480	0.0570*
H25B	0.94060	1.17920	0.81970	0.0570*
H26A	0.79680	1.11660	0.71010	0.0960*
H26B	0.86920	1.26040	0.72130	0.0960*
H26C	0.75340	1.21980	0.76390	0.0960*

	U11	U22	U33	U12	U13	U23
Br1	0.0375 (3)	0.0761 (5)	0.0421 (3)	0.0165 (3)	0.0082 (2)	−0.0099 (3)
N1	0.023 (2)	0.035 (3)	0.0199 (19)	0.0012 (18)	0.0009 (16)	0.0006 (17)
N2	0.029 (2)	0.036 (3)	0.0225 (19)	0.0029 (19)	0.0050 (17)	−0.0002 (18)
C1	0.024 (2)	0.032 (3)	0.024 (2)	−0.001 (2)	0.0039 (19)	0.002 (2)
C2	0.030 (2)	0.027 (3)	0.023 (2)	0.002 (2)	0.004 (2)	0.004 (2)
C3	0.027 (2)	0.035 (3)	0.025 (2)	0.001 (2)	0.007 (2)	0.002 (2)
C4	0.027 (2)	0.040 (3)	0.019 (2)	0.000 (2)	0.0001 (19)	−0.002 (2)
C5	0.035 (3)	0.042 (4)	0.022 (2)	0.007 (2)	0.001 (2)	0.000 (2)
C6	0.036 (3)	0.035 (4)	0.028 (2)	0.007 (2)	−0.003 (2)	−0.001 (2)
C7	0.027 (2)	0.044 (4)	0.031 (3)	0.000 (2)	0.002 (2)	−0.014 (2)
C8	0.030 (3)	0.055 (4)	0.022 (2)	0.001 (3)	0.006 (2)	0.001 (2)
C9	0.034 (3)	0.030 (3)	0.023 (2)	0.006 (2)	0.003 (2)	−0.003 (2)
C10	0.028 (2)	0.037 (4)	0.021 (2)	−0.003 (2)	0.0027 (19)	0.000 (2)
C11	0.041 (3)	0.045 (4)	0.035 (3)	0.006 (3)	0.000 (2)	−0.003 (2)
C12	0.046 (3)	0.076 (5)	0.038 (3)	0.012 (3)	−0.011 (2)	−0.001 (3)
C13	0.032 (3)	0.077 (5)	0.051 (3)	0.011 (3)	−0.001 (3)	0.017 (3)
C14	0.042 (3)	0.053 (4)	0.044 (3)	0.012 (3)	0.008 (2)	0.008 (3)
C15	0.032 (3)	0.046 (4)	0.025 (2)	0.004 (2)	−0.002 (2)	0.003 (2)
C16	0.031 (3)	0.034 (3)	0.021 (2)	0.007 (2)	0.0010 (19)	0.003 (2)
C17	0.035 (3)	0.058 (4)	0.035 (3)	0.000 (3)	0.005 (2)	−0.009 (3)
C18	0.044 (3)	0.077 (5)	0.038 (3)	0.006 (3)	0.015 (3)	−0.008 (3)
C19	0.061 (4)	0.061 (5)	0.023 (3)	0.018 (3)	0.011 (3)	−0.002 (3)
C20	0.069 (4)	0.043 (4)	0.028 (3)	0.001 (3)	−0.002 (3)	−0.009 (2)
C21	0.054 (3)	0.031 (3)	0.025 (2)	0.001 (3)	0.006 (2)	0.004 (2)
C22	0.023 (2)	0.042 (4)	0.026 (2)	0.003 (2)	−0.0008 (19)	0.000 (2)
C23	0.032 (2)	0.038 (3)	0.024 (2)	−0.003 (2)	0.0048 (19)	0.001 (2)
C24	0.036 (3)	0.045 (4)	0.027 (2)	0.004 (3)	0.002 (2)	0.004 (2)
C25	0.043 (3)	0.064 (5)	0.037 (3)	0.003 (3)	0.005 (2)	0.020 (3)
C26	0.071 (4)	0.069 (5)	0.052 (3)	0.007 (4)	0.008 (3)	0.023 (3)

Br1—C7	1.893 (4)	C23—C24	1.509 (6)
N1—C1	1.368 (5)	C24—C25	1.497 (7)
N1—C3	1.365 (6)	C25—C26	1.516 (7)
N1—C22	1.478 (5)	C5—H5	0.9500
N2—C1	1.313 (5)	C6—H6	0.9500
N2—C2	1.372 (5)	C8—H8	0.9500
C1—C4	1.454 (6)	C9—H9	0.9500
C2—C3	1.376 (6)	C11—H11	0.9500
C2—C10	1.443 (6)	C12—H12	0.9500
C3—C16	1.477 (6)	C13—H13	0.9500
C4—C5	1.399 (6)	C14—H14	0.9500
C4—C9	1.382 (6)	C15—H15	0.9500
C5—C6	1.365 (6)	C17—H17	0.9500
C6—C7	1.364 (6)	C18—H18	0.9500
C7—C8	1.372 (7)	C19—H19	0.9500
C8—C9	1.380 (6)	C20—H20	0.9500
C10—C11	1.392 (6)	C21—H21	0.9500
C10—C15	1.374 (7)	C22—H22A	0.9900
C11—C12	1.378 (7)	C22—H22B	0.9900
C12—C13	1.363 (8)	C23—H23A	0.9900
C13—C14	1.386 (7)	C23—H23B	0.9900
C14—C15	1.383 (6)	C24—H24A	0.9900
C16—C17	1.384 (6)	C24—H24B	0.9900
C16—C21	1.369 (7)	C25—H25A	0.9900
C17—C18	1.385 (7)	C25—H25B	0.9900
C18—C19	1.355 (8)	C26—H26A	0.9800
C19—C20	1.375 (7)	C26—H26B	0.9800
C20—C21	1.393 (6)	C26—H26C	0.9800
C22—C23	1.486 (6)
C1—N1—C3	107.4 (3)	C4—C9—H9	120.00
C1—N1—C22	126.8 (4)	C8—C9—H9	120.00
C3—N1—C22	125.2 (3)	C10—C11—H11	120.00
C1—N2—C2	106.8 (3)	C12—C11—H11	120.00
N1—C1—N2	110.6 (4)	C11—C12—H12	120.00
N1—C1—C4	125.9 (4)	C13—C12—H12	120.00
N2—C1—C4	123.1 (4)	C12—C13—H13	120.00
N2—C2—C3	109.1 (4)	C14—C13—H13	120.00
N2—C2—C10	120.7 (3)	C13—C14—H14	120.00
C3—C2—C10	130.1 (4)	C15—C14—H14	120.00
N1—C3—C2	106.1 (4)	C10—C15—H15	119.00
N1—C3—C16	122.0 (4)	C14—C15—H15	119.00
C2—C3—C16	131.9 (4)	C16—C17—H17	120.00
C1—C4—C5	124.2 (4)	C18—C17—H17	120.00
C1—C4—C9	117.7 (4)	C17—C18—H18	120.00
C5—C4—C9	118.1 (4)	C19—C18—H18	120.00
C4—C5—C6	121.2 (4)	C18—C19—H19	120.00
C5—C6—C7	119.2 (4)	C20—C19—H19	120.00
Br1—C7—C6	119.7 (3)	C19—C20—H20	120.00
Br1—C7—C8	118.7 (3)	C21—C20—H20	120.00
C6—C7—C8	121.6 (4)	C16—C21—H21	120.00
C7—C8—C9	119.1 (4)	C20—C21—H21	120.00
C4—C9—C8	120.8 (4)	N1—C22—H22A	109.00
C2—C10—C11	119.7 (4)	N1—C22—H22B	109.00
C2—C10—C15	122.2 (4)	C23—C22—H22A	109.00
C11—C10—C15	118.0 (4)	C23—C22—H22B	109.00
C10—C11—C12	120.6 (5)	H22A—C22—H22B	108.00
C11—C12—C13	120.9 (5)	C22—C23—H23A	109.00
C12—C13—C14	119.4 (5)	C22—C23—H23B	109.00
C13—C14—C15	119.7 (5)	C24—C23—H23A	109.00
C10—C15—C14	121.4 (4)	C24—C23—H23B	109.00
C3—C16—C17	119.2 (4)	H23A—C23—H23B	108.00
C3—C16—C21	122.1 (4)	C23—C24—H24A	109.00
C17—C16—C21	118.8 (4)	C23—C24—H24B	109.00
C16—C17—C18	120.2 (5)	C25—C24—H24A	109.00
C17—C18—C19	120.6 (5)	C25—C24—H24B	109.00
C18—C19—C20	120.2 (4)	H24A—C24—H24B	108.00
C19—C20—C21	119.4 (5)	C24—C25—H25A	109.00
C16—C21—C20	120.9 (5)	C24—C25—H25B	109.00
N1—C22—C23	111.3 (3)	C26—C25—H25A	109.00
C22—C23—C24	112.4 (4)	C26—C25—H25B	109.00
C23—C24—C25	113.5 (4)	H25A—C25—H25B	108.00
C24—C25—C26	113.1 (4)	C25—C26—H26A	109.00
C4—C5—H5	119.00	C25—C26—H26B	110.00
C6—C5—H5	119.00	C25—C26—H26C	110.00
C5—C6—H6	120.00	H26A—C26—H26B	109.00
C7—C6—H6	120.00	H26A—C26—H26C	109.00
C7—C8—H8	120.00	H26B—C26—H26C	109.00
C9—C8—H8	120.00
C3—N1—C1—N2	−1.2 (5)	C1—C4—C5—C6	179.0 (4)
C3—N1—C1—C4	−173.4 (4)	C9—C4—C5—C6	−2.3 (7)
C22—N1—C1—N2	−173.0 (4)	C1—C4—C9—C8	−179.5 (4)
C22—N1—C1—C4	14.9 (7)	C5—C4—C9—C8	1.6 (7)
C1—N1—C3—C2	0.8 (5)	C4—C5—C6—C7	0.8 (7)
C1—N1—C3—C16	−178.5 (4)	C5—C6—C7—Br1	178.7 (3)
C22—N1—C3—C2	172.8 (4)	C5—C6—C7—C8	1.2 (7)
C22—N1—C3—C16	−6.5 (7)	Br1—C7—C8—C9	−179.3 (3)
C1—N1—C22—C23	93.6 (5)	C6—C7—C8—C9	−1.8 (7)
C3—N1—C22—C23	−76.8 (5)	C7—C8—C9—C4	0.3 (7)
C2—N2—C1—N1	1.0 (5)	C2—C10—C11—C12	178.8 (4)
C2—N2—C1—C4	173.5 (4)	C15—C10—C11—C12	0.1 (7)
C1—N2—C2—C3	−0.5 (5)	C2—C10—C15—C14	−178.3 (4)
C1—N2—C2—C10	−179.9 (4)	C11—C10—C15—C14	0.3 (7)
N1—C1—C4—C5	−47.0 (7)	C10—C11—C12—C13	0.1 (8)
N1—C1—C4—C9	134.3 (5)	C11—C12—C13—C14	−0.6 (8)
N2—C1—C4—C5	141.8 (5)	C12—C13—C14—C15	1.0 (7)
N2—C1—C4—C9	−36.9 (7)	C13—C14—C15—C10	−0.9 (7)
N2—C2—C3—N1	−0.2 (5)	C3—C16—C17—C18	179.5 (5)
N2—C2—C3—C16	179.0 (5)	C21—C16—C17—C18	−1.0 (7)
C10—C2—C3—N1	179.1 (5)	C3—C16—C21—C20	179.9 (4)
C10—C2—C3—C16	−1.7 (9)	C17—C16—C21—C20	0.4 (7)
N2—C2—C10—C11	−29.8 (6)	C16—C17—C18—C19	1.6 (8)
N2—C2—C10—C15	148.8 (4)	C17—C18—C19—C20	−1.6 (8)
C3—C2—C10—C11	150.9 (5)	C18—C19—C20—C21	0.9 (8)
C3—C2—C10—C15	−30.5 (8)	C19—C20—C21—C16	−0.3 (8)
N1—C3—C16—C17	115.2 (5)	N1—C22—C23—C24	−169.5 (3)
N1—C3—C16—C21	−64.3 (6)	C22—C23—C24—C25	178.1 (4)
C2—C3—C16—C17	−63.9 (7)	C23—C24—C25—C26	−176.0 (4)
C2—C3—C16—C21	116.6 (6)