2-(4-Bromo­phen­yl)-1-pentyl-4,5-diphenyl-1H-imidazole

Mohamed, S.K.; Akkurt, M.; Singh, K.; Marzouk, A.A.; Albayati, M.R.

doi:10.1107/S1600536813021983

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1417

doi:10.1107/S1600536813021983

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2-(4-Bromophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole

Shaaban K. Mohamed,^a,^b Mehmet Akkurt,^c Kuldip Singh,^d Adel A. Marzouk ^e and Mustafa R. Albayati ^f ^*

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dDepartment of Chemistry, University of Leicester, Leicester, England, ^ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 6 August 2013; accepted 6 August 2013; online 14 August 2013)

The title compound, C₂₆H₂₅BrN₂, is isomorphous with the chloro derivative [2-(4-chlorophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole; Mohamed et al. (2013 ). Acta Cryst. E69, o846–o847]. The two phenyl rings and the 4-bromophenyl 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, molecules stack in columns along the b-axis direction, however, there are no significant intermolecular interactions 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_r = 445.39
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.066
wR(F²) = 0.116
S = 0.88
4329 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813021983/su2633sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813021983/su2633Isup3.cml

checkCIF report

Comment top

Many substituted imidazoles exhibit diverse pharmaceutical properties and are known inhibitors of fungicides and herbicides, plant growth regulators and therapeutic agents (Maier et al., 1989a,b). Moreover, they are of interest for environmental and green chemistry applications, and have been prepared and used as a large class of ionic liquids and Lewis base catalysts (Welton, 1999; Hermann & Kocher, 1997). As part of our ongoing study of the synthesis (Akkurt et al., 2013; Mohamed et al., 2013; Simpson et al., 2013) and biological applications of tetrasubstituted imidazoles, we herein report on the synthesize and crystal structure of the title compound.

The title compound, Fig. 1, and the chloro derivative, 2-(4-Chlorophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole, whose crystal structure has been reported by (Mohamed et al., 2013), are isomorphous. In the title compound the phenyl rings (C10–C15 and C16–C21) and the 4-bromophenyl ring (C4–C9) make dihedral angles of 30.1 (2), 64.3 (3) and 42.0 (2)°, respectively, with the imidazole ring (N1/N2/C1–C3). The values of the bond lengths and bond angles fall within the normal range and are comparable with those reported for similar structures (Akkurt et al., 2013; Mohamed et al., 2013; Simpson et al., 2013).

In the crystal, the molecules stack in columns along the b axis direction however, there are no significant intermolecular interactions present (Fig. 2).

Related literature top

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 top

The title compound was synthesized following our previously reported procedure (Mohamed et al., 2013). Colourless plates of the title compound (M.p. 396–398 K) were collected with 84% yield. Crystals of sufficient quality for the X-ray diffraction study were obtained by slow evaporation of an ethanol solution of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis.

2-(4-Bromophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole top

Crystal data top

C₂₆H₂₅BrN₂	F(000) = 920
M_r = 445.39	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0277P)²] where P = (F_o² + 2F_c²)/3
4329 reflections	(Δ/σ)_max = 0.001
263 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −1.05 e Å⁻³

Crystal data top

C₂₆H₂₅BrN₂	V = 2209.4 (19) Å³
M_r = 445.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.665 (5) Å	µ = 1.88 mm⁻¹
b = 9.619 (5) Å	T = 150 K
c = 21.541 (10) Å	0.36 × 0.16 × 0.03 mm
β = 91.092 (9)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4329 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2011)	2328 reflections with I > 2σ(I)
T_min = 0.600, T_max = 0.969	R_int = 0.187
16966 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 0.88	Δρ_max = 0.61 e Å⁻³
4329 reflections	Δρ_min = −1.05 e Å⁻³
263 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅BrN₂
M_r	445.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	10.665 (5), 9.619 (5), 21.541 (10)
β (°)	91.092 (9)
V (Å³)	2209.4 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.36 × 0.16 × 0.03

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2011)
T_min, T_max	0.600, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	16966, 4329, 2328
R_int	0.187
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.116, 0.88
No. of reflections	4329
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −1.05

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Acknowledgements

Manchester Metropolitan University, Erciyes University and the University of Leicester are gratefully acknowledged for supporting this study.

References

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