organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Mohamed, S. K., Akkurt, M., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o1243.]). 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[Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989a). US Patent 4820335.],b[Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989b). Chem. Abstr. 111, 19494.]); Welton (1999[Welton, T. (1999). Chem. Rev. 99, 2071-2084.]); Hermann & Kocher (1997[Hermann, W. A. & Kocher, C. (1997). Angew. Chem. Int. Ed. Engl. 36, 2162-2187.]). For related structures, see: Akkurt et al. (2013[Akkurt, M., Mohamed, S. K., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o846-o847.]); Mohamed et al. (2013[Mohamed, S. K., Akkurt, M., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o1243.]); Simpson et al. (2013[Simpson, J., Mohamed, S. K., Marzouk, A. A., Talybov, A. H. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o5-o6.]).

[Scheme 1]

Experimental

Crystal data
  • C26H25BrN2

  • Mr = 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[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.600, Tmax = 0.969

  • 16966 measured reflections

  • 4329 independent reflections

  • 2328 reflections with I > 2σ(I)

  • Rint = 0.187

Refinement
  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 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[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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.

Refinement top

All H atoms were placed in geometrically idealized positions with C—H = 0.95 - 0.99 Å and refined using a riding model with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms. The Rint value is rather high probably due to the fact that the crystal diffracted weakly beyond 22° in θ.

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
[Figure 1] Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] 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
C26H25BrN2F(000) = 920
Mr = 445.39Dx = 1.339 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 638 reflections
a = 10.665 (5) Åθ = 2.3–23.5°
b = 9.619 (5) ŵ = 1.88 mm1
c = 21.541 (10) ÅT = 150 K
β = 91.092 (9)°Plate, colourless
V = 2209.4 (19) Å30.36 × 0.16 × 0.03 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
4329 independent reflections
Radiation source: fine-focus sealed tube2328 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.187
ϕ and ο scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
h = 1313
Tmin = 0.600, Tmax = 0.969k = 1111
16966 measured reflectionsl = 2526
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-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 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 1.05 e Å3
Crystal data top
C26H25BrN2V = 2209.4 (19) Å3
Mr = 445.39Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.665 (5) ŵ = 1.88 mm1
b = 9.619 (5) ÅT = 150 K
c = 21.541 (10) Å0.36 × 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)
Tmin = 0.600, Tmax = 0.969Rint = 0.187
16966 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 0.88Δρmax = 0.61 e Å3
4329 reflectionsΔρmin = 1.05 e Å3
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
xyzUiso*/Ueq
Br10.48280 (5)1.06999 (7)1.12186 (2)0.0518 (2)
N10.9579 (3)0.7532 (4)0.95097 (14)0.0260 (14)
N21.0328 (3)0.7435 (4)1.04691 (14)0.0291 (14)
C10.9420 (4)0.7928 (5)1.01128 (18)0.0266 (14)
C21.1118 (4)0.6715 (5)1.00900 (18)0.0266 (14)
C31.0659 (4)0.6773 (5)0.94893 (18)0.0289 (14)
C40.8327 (4)0.8632 (5)1.03554 (18)0.0287 (14)
C50.7751 (4)0.9785 (5)1.00753 (18)0.0330 (18)
C60.6714 (4)1.0384 (5)1.03236 (18)0.0331 (18)
C70.6244 (4)0.9856 (5)1.08588 (19)0.0340 (18)
C80.6802 (4)0.8754 (6)1.11597 (19)0.0356 (18)
C90.7843 (4)0.8143 (5)1.09045 (18)0.0290 (16)
C101.2222 (4)0.6036 (5)1.03414 (18)0.0286 (16)
C111.2824 (4)0.6578 (5)1.0867 (2)0.0403 (19)
C121.3866 (5)0.5930 (7)1.1121 (2)0.054 (2)
C131.4331 (5)0.4747 (6)1.0864 (2)0.053 (2)
C141.3738 (4)0.4185 (6)1.0344 (2)0.0462 (19)
C151.2697 (4)0.4841 (5)1.00872 (19)0.0344 (18)
C161.1136 (4)0.6206 (5)0.89021 (18)0.0287 (16)
C171.2266 (4)0.6687 (6)0.8681 (2)0.0426 (19)
C181.2736 (5)0.6162 (6)0.8134 (2)0.053 (2)
C191.2084 (5)0.5199 (6)0.7801 (2)0.048 (2)
C201.0959 (5)0.4708 (6)0.80118 (19)0.047 (2)
C211.0490 (5)0.5224 (5)0.85652 (18)0.0366 (16)
C220.8836 (4)0.7999 (5)0.89621 (18)0.0304 (16)
C230.9433 (4)0.9208 (5)0.86564 (18)0.0313 (14)
C240.8586 (4)0.9869 (5)0.81709 (19)0.0360 (18)
C250.9148 (4)1.1120 (6)0.7870 (2)0.048 (2)
C260.8257 (5)1.1835 (6)0.7416 (2)0.064 (2)
H50.808601.015700.970500.0400*
H60.632501.115901.012600.0400*
H80.647500.841601.153800.0430*
H90.823200.737701.110900.0350*
H111.251300.740201.105200.0480*
H121.426600.631301.148000.0640*
H131.505300.431101.104100.0640*
H141.404600.335301.016400.0560*
H151.230100.445800.972700.0410*
H171.272000.737900.890400.0510*
H181.352300.648000.799100.0630*
H191.240600.486200.742100.0580*
H201.050500.402300.778200.0560*
H210.971100.489000.871100.0440*
H22A0.798300.825900.909300.0360*
H22B0.875700.722400.866100.0360*
H23A1.021600.889900.845900.0380*
H23B0.965800.991000.897500.0380*
H24A0.838300.917100.784600.0430*
H24B0.779001.014300.836700.0430*
H25A0.991101.083400.764800.0570*
H25B0.940601.179200.819700.0570*
H26A0.796801.116600.710100.0960*
H26B0.869201.260400.721300.0960*
H26C0.753401.219800.763900.0960*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0375 (3)0.0761 (5)0.0421 (3)0.0165 (3)0.0082 (2)0.0099 (3)
N10.023 (2)0.035 (3)0.0199 (19)0.0012 (18)0.0009 (16)0.0006 (17)
N20.029 (2)0.036 (3)0.0225 (19)0.0029 (19)0.0050 (17)0.0002 (18)
C10.024 (2)0.032 (3)0.024 (2)0.001 (2)0.0039 (19)0.002 (2)
C20.030 (2)0.027 (3)0.023 (2)0.002 (2)0.004 (2)0.004 (2)
C30.027 (2)0.035 (3)0.025 (2)0.001 (2)0.007 (2)0.002 (2)
C40.027 (2)0.040 (3)0.019 (2)0.000 (2)0.0001 (19)0.002 (2)
C50.035 (3)0.042 (4)0.022 (2)0.007 (2)0.001 (2)0.000 (2)
C60.036 (3)0.035 (4)0.028 (2)0.007 (2)0.003 (2)0.001 (2)
C70.027 (2)0.044 (4)0.031 (3)0.000 (2)0.002 (2)0.014 (2)
C80.030 (3)0.055 (4)0.022 (2)0.001 (3)0.006 (2)0.001 (2)
C90.034 (3)0.030 (3)0.023 (2)0.006 (2)0.003 (2)0.003 (2)
C100.028 (2)0.037 (4)0.021 (2)0.003 (2)0.0027 (19)0.000 (2)
C110.041 (3)0.045 (4)0.035 (3)0.006 (3)0.000 (2)0.003 (2)
C120.046 (3)0.076 (5)0.038 (3)0.012 (3)0.011 (2)0.001 (3)
C130.032 (3)0.077 (5)0.051 (3)0.011 (3)0.001 (3)0.017 (3)
C140.042 (3)0.053 (4)0.044 (3)0.012 (3)0.008 (2)0.008 (3)
C150.032 (3)0.046 (4)0.025 (2)0.004 (2)0.002 (2)0.003 (2)
C160.031 (3)0.034 (3)0.021 (2)0.007 (2)0.0010 (19)0.003 (2)
C170.035 (3)0.058 (4)0.035 (3)0.000 (3)0.005 (2)0.009 (3)
C180.044 (3)0.077 (5)0.038 (3)0.006 (3)0.015 (3)0.008 (3)
C190.061 (4)0.061 (5)0.023 (3)0.018 (3)0.011 (3)0.002 (3)
C200.069 (4)0.043 (4)0.028 (3)0.001 (3)0.002 (3)0.009 (2)
C210.054 (3)0.031 (3)0.025 (2)0.001 (3)0.006 (2)0.004 (2)
C220.023 (2)0.042 (4)0.026 (2)0.003 (2)0.0008 (19)0.000 (2)
C230.032 (2)0.038 (3)0.024 (2)0.003 (2)0.0048 (19)0.001 (2)
C240.036 (3)0.045 (4)0.027 (2)0.004 (3)0.002 (2)0.004 (2)
C250.043 (3)0.064 (5)0.037 (3)0.003 (3)0.005 (2)0.020 (3)
C260.071 (4)0.069 (5)0.052 (3)0.007 (4)0.008 (3)0.023 (3)
Geometric parameters (Å, º) top
Br1—C71.893 (4)C23—C241.509 (6)
N1—C11.368 (5)C24—C251.497 (7)
N1—C31.365 (6)C25—C261.516 (7)
N1—C221.478 (5)C5—H50.9500
N2—C11.313 (5)C6—H60.9500
N2—C21.372 (5)C8—H80.9500
C1—C41.454 (6)C9—H90.9500
C2—C31.376 (6)C11—H110.9500
C2—C101.443 (6)C12—H120.9500
C3—C161.477 (6)C13—H130.9500
C4—C51.399 (6)C14—H140.9500
C4—C91.382 (6)C15—H150.9500
C5—C61.365 (6)C17—H170.9500
C6—C71.364 (6)C18—H180.9500
C7—C81.372 (7)C19—H190.9500
C8—C91.380 (6)C20—H200.9500
C10—C111.392 (6)C21—H210.9500
C10—C151.374 (7)C22—H22A0.9900
C11—C121.378 (7)C22—H22B0.9900
C12—C131.363 (8)C23—H23A0.9900
C13—C141.386 (7)C23—H23B0.9900
C14—C151.383 (6)C24—H24A0.9900
C16—C171.384 (6)C24—H24B0.9900
C16—C211.369 (7)C25—H25A0.9900
C17—C181.385 (7)C25—H25B0.9900
C18—C191.355 (8)C26—H26A0.9800
C19—C201.375 (7)C26—H26B0.9800
C20—C211.393 (6)C26—H26C0.9800
C22—C231.486 (6)
C1—N1—C3107.4 (3)C4—C9—H9120.00
C1—N1—C22126.8 (4)C8—C9—H9120.00
C3—N1—C22125.2 (3)C10—C11—H11120.00
C1—N2—C2106.8 (3)C12—C11—H11120.00
N1—C1—N2110.6 (4)C11—C12—H12120.00
N1—C1—C4125.9 (4)C13—C12—H12120.00
N2—C1—C4123.1 (4)C12—C13—H13120.00
N2—C2—C3109.1 (4)C14—C13—H13120.00
N2—C2—C10120.7 (3)C13—C14—H14120.00
C3—C2—C10130.1 (4)C15—C14—H14120.00
N1—C3—C2106.1 (4)C10—C15—H15119.00
N1—C3—C16122.0 (4)C14—C15—H15119.00
C2—C3—C16131.9 (4)C16—C17—H17120.00
C1—C4—C5124.2 (4)C18—C17—H17120.00
C1—C4—C9117.7 (4)C17—C18—H18120.00
C5—C4—C9118.1 (4)C19—C18—H18120.00
C4—C5—C6121.2 (4)C18—C19—H19120.00
C5—C6—C7119.2 (4)C20—C19—H19120.00
Br1—C7—C6119.7 (3)C19—C20—H20120.00
Br1—C7—C8118.7 (3)C21—C20—H20120.00
C6—C7—C8121.6 (4)C16—C21—H21120.00
C7—C8—C9119.1 (4)C20—C21—H21120.00
C4—C9—C8120.8 (4)N1—C22—H22A109.00
C2—C10—C11119.7 (4)N1—C22—H22B109.00
C2—C10—C15122.2 (4)C23—C22—H22A109.00
C11—C10—C15118.0 (4)C23—C22—H22B109.00
C10—C11—C12120.6 (5)H22A—C22—H22B108.00
C11—C12—C13120.9 (5)C22—C23—H23A109.00
C12—C13—C14119.4 (5)C22—C23—H23B109.00
C13—C14—C15119.7 (5)C24—C23—H23A109.00
C10—C15—C14121.4 (4)C24—C23—H23B109.00
C3—C16—C17119.2 (4)H23A—C23—H23B108.00
C3—C16—C21122.1 (4)C23—C24—H24A109.00
C17—C16—C21118.8 (4)C23—C24—H24B109.00
C16—C17—C18120.2 (5)C25—C24—H24A109.00
C17—C18—C19120.6 (5)C25—C24—H24B109.00
C18—C19—C20120.2 (4)H24A—C24—H24B108.00
C19—C20—C21119.4 (5)C24—C25—H25A109.00
C16—C21—C20120.9 (5)C24—C25—H25B109.00
N1—C22—C23111.3 (3)C26—C25—H25A109.00
C22—C23—C24112.4 (4)C26—C25—H25B109.00
C23—C24—C25113.5 (4)H25A—C25—H25B108.00
C24—C25—C26113.1 (4)C25—C26—H26A109.00
C4—C5—H5119.00C25—C26—H26B110.00
C6—C5—H5119.00C25—C26—H26C110.00
C5—C6—H6120.00H26A—C26—H26B109.00
C7—C6—H6120.00H26A—C26—H26C109.00
C7—C8—H8120.00H26B—C26—H26C109.00
C9—C8—H8120.00
C3—N1—C1—N21.2 (5)C1—C4—C5—C6179.0 (4)
C3—N1—C1—C4173.4 (4)C9—C4—C5—C62.3 (7)
C22—N1—C1—N2173.0 (4)C1—C4—C9—C8179.5 (4)
C22—N1—C1—C414.9 (7)C5—C4—C9—C81.6 (7)
C1—N1—C3—C20.8 (5)C4—C5—C6—C70.8 (7)
C1—N1—C3—C16178.5 (4)C5—C6—C7—Br1178.7 (3)
C22—N1—C3—C2172.8 (4)C5—C6—C7—C81.2 (7)
C22—N1—C3—C166.5 (7)Br1—C7—C8—C9179.3 (3)
C1—N1—C22—C2393.6 (5)C6—C7—C8—C91.8 (7)
C3—N1—C22—C2376.8 (5)C7—C8—C9—C40.3 (7)
C2—N2—C1—N11.0 (5)C2—C10—C11—C12178.8 (4)
C2—N2—C1—C4173.5 (4)C15—C10—C11—C120.1 (7)
C1—N2—C2—C30.5 (5)C2—C10—C15—C14178.3 (4)
C1—N2—C2—C10179.9 (4)C11—C10—C15—C140.3 (7)
N1—C1—C4—C547.0 (7)C10—C11—C12—C130.1 (8)
N1—C1—C4—C9134.3 (5)C11—C12—C13—C140.6 (8)
N2—C1—C4—C5141.8 (5)C12—C13—C14—C151.0 (7)
N2—C1—C4—C936.9 (7)C13—C14—C15—C100.9 (7)
N2—C2—C3—N10.2 (5)C3—C16—C17—C18179.5 (5)
N2—C2—C3—C16179.0 (5)C21—C16—C17—C181.0 (7)
C10—C2—C3—N1179.1 (5)C3—C16—C21—C20179.9 (4)
C10—C2—C3—C161.7 (9)C17—C16—C21—C200.4 (7)
N2—C2—C10—C1129.8 (6)C16—C17—C18—C191.6 (8)
N2—C2—C10—C15148.8 (4)C17—C18—C19—C201.6 (8)
C3—C2—C10—C11150.9 (5)C18—C19—C20—C210.9 (8)
C3—C2—C10—C1530.5 (8)C19—C20—C21—C160.3 (8)
N1—C3—C16—C17115.2 (5)N1—C22—C23—C24169.5 (3)
N1—C3—C16—C2164.3 (6)C22—C23—C24—C25178.1 (4)
C2—C3—C16—C1763.9 (7)C23—C24—C25—C26176.0 (4)
C2—C3—C16—C21116.6 (6)

Experimental details

Crystal data
Chemical formulaC26H25BrN2
Mr445.39
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)10.665 (5), 9.619 (5), 21.541 (10)
β (°) 91.092 (9)
V3)2209.4 (19)
Z4
Radiation typeMo Kα
µ (mm1)1.88
Crystal size (mm)0.36 × 0.16 × 0.03
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2011)
Tmin, Tmax0.600, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
16966, 4329, 2328
Rint0.187
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.116, 0.88
No. of reflections4329
No. of parameters263
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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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