organic compounds
N′-[(E)-1-(4-Bromophenyl)ethylidene]-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and cDepartment of Chemistry, Canara Engineering College, Mangalore 574 219, India
*Correspondence e-mail: hkfun@usm.my
In the title compound, C14H14BrN5O3, the mean plane of the imidazole ring (r.m.s deviation = 0.004 Å) forms a dihedral angle of 58.13 (7)° with the benzene ring. In the crystal, molecules are linked via N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds into a three-dimensional network. A short Br⋯Br contact of 3.4932 (2) Å also occurs.
Related literature
For general background to and applications of imidazole derivatives, see: Priya & Kalluraya (2005); Krapcho & Turk (1966); Chu et al. (2004); Khalafi-Nezhad et al. (2005). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S160053681202795X/rz2774sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202795X/rz2774Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681202795X/rz2774Isup3.cml
The title compound was synthesized by refluxing a mixture of 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acethydrazide (0.1 mol) and 1-(4-bromophenyl)ethanone (0.1 mol) in glacial acetic acid for 1 hour. After cooling the reaction mixture to room temperature and evaporation of the solvent under reduced pressure, the solid separated was filtered, washed with water and dried. The recrystallization of the sample was done using an ethanol-dioxane (1:1 v/v) mixture. The melting point of the compound was found to be 549 K. The slow evaporation of the ethanol-dioxane mixture of the compound gave crystals suitable for X-ray analysis.
Atom H1N2 was located in a difference Fourier map and refined freely [N–H = 0.81 (2) Å]. All other hydrogen atoms were positioned geometrically and refined using a riding model with C–H = 0.95-0.99 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for the methyl groups.
The chemistry of imidazole derivatives has been the subject of much interest due to their importance in various applications and also due to their widespread potential as well as proven biological and pharmacological activities (Priya & Kalluraya, 2005). Various applications of imidazoles have been listed in the literature with functions as widely divergent as antidepressant agents (Krapcho & Turk, 1966), as a marker for imaging tumor hypoxia( Chu et al., 2004), and in antibacterial activity (Khalafi-Nezhad et al., 2005). In view of the obvious importance of imidazole derivatives as potential pharmacological agents, herein we report the
of the above imidazole derivative.In the title molecule, Fig. 1, the mean plane of the imidazole ring (N3/N4/C10-C12, r.m.s deviation = 0.004 Å) forms a dihedral angle of 58.13 (7)° with the phenyl ring (C1-C6). Bond lengths (Allen et al., 1987) and angles are within normal ranges. A short Br1···Br1 contact of 3.4932 (2) Å also occurs. In the crystal (Fig. 2), molecules are linked via intermolecular N2–H1N2···O1, C9–H9A···O3, C9–H9B···N4 and C10–H10A···O2 hydrogen bonds (Table 1) into a three-dimensional network.
For general background to and applications of imidazole derivatives, see: Priya & Kalluraya (2005); Krapcho & Turk (1966); Chu et al. (2004); Khalafi-Nezhad et al. (2005). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C14H14BrN5O3 | F(000) = 768 |
Mr = 380.21 | Dx = 1.610 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9969 reflections |
a = 8.4176 (1) Å | θ = 2.3–33.5° |
b = 10.6541 (1) Å | µ = 2.64 mm−1 |
c = 17.4933 (2) Å | T = 100 K |
β = 90.100 (1)° | Block, yellow |
V = 1568.83 (3) Å3 | 0.37 × 0.33 × 0.15 mm |
Z = 4 |
Bruker SMART APEXII CCD area-detector diffractometer | 6320 independent reflections |
Radiation source: fine-focus sealed tube | 5026 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
φ and ω scans | θmax = 33.9°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→13 |
Tmin = 0.441, Tmax = 0.701 | k = −16→16 |
45099 measured reflections | l = −27→27 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0423P)2 + 0.4612P] where P = (Fo2 + 2Fc2)/3 |
6320 reflections | (Δ/σ)max = 0.001 |
214 parameters | Δρmax = 0.88 e Å−3 |
0 restraints | Δρmin = −0.66 e Å−3 |
C14H14BrN5O3 | V = 1568.83 (3) Å3 |
Mr = 380.21 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.4176 (1) Å | µ = 2.64 mm−1 |
b = 10.6541 (1) Å | T = 100 K |
c = 17.4933 (2) Å | 0.37 × 0.33 × 0.15 mm |
β = 90.100 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 6320 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 5026 reflections with I > 2σ(I) |
Tmin = 0.441, Tmax = 0.701 | Rint = 0.040 |
45099 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.88 e Å−3 |
6320 reflections | Δρmin = −0.66 e Å−3 |
214 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) 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 | 0.021322 (19) | −0.359303 (13) | 0.050226 (9) | 0.03144 (5) | |
O1 | 0.45656 (12) | 0.54105 (9) | 0.08914 (5) | 0.02360 (19) | |
O2 | 0.13283 (13) | 0.85764 (9) | 0.31753 (6) | 0.0269 (2) | |
O3 | −0.04787 (11) | 0.73832 (11) | 0.26628 (7) | 0.0345 (3) | |
N1 | 0.33805 (12) | 0.23194 (9) | 0.05430 (6) | 0.01687 (18) | |
N2 | 0.40021 (13) | 0.34967 (10) | 0.04122 (6) | 0.01891 (19) | |
N3 | 0.31916 (11) | 0.50038 (9) | 0.22432 (6) | 0.01478 (17) | |
N4 | 0.36372 (12) | 0.68190 (10) | 0.28408 (6) | 0.01722 (18) | |
N5 | 0.09082 (13) | 0.76031 (10) | 0.28541 (7) | 0.0215 (2) | |
C1 | 0.29424 (16) | −0.06979 (12) | −0.03559 (7) | 0.0221 (2) | |
H1A | 0.3658 | −0.0588 | −0.0770 | 0.026* | |
C2 | 0.22669 (16) | −0.18701 (12) | −0.02307 (8) | 0.0241 (2) | |
H2A | 0.2518 | −0.2559 | −0.0553 | 0.029* | |
C3 | 0.12217 (16) | −0.20161 (12) | 0.03723 (8) | 0.0229 (2) | |
C4 | 0.08571 (16) | −0.10281 (12) | 0.08621 (7) | 0.0212 (2) | |
H4A | 0.0153 | −0.1149 | 0.1280 | 0.025* | |
C5 | 0.15433 (14) | 0.01392 (11) | 0.07288 (7) | 0.0184 (2) | |
H5A | 0.1300 | 0.0822 | 0.1058 | 0.022* | |
C6 | 0.25865 (14) | 0.03226 (11) | 0.01173 (7) | 0.0181 (2) | |
C7 | 0.32849 (15) | 0.15744 (11) | −0.00367 (7) | 0.0182 (2) | |
C8 | 0.40582 (14) | 0.43392 (11) | 0.09867 (7) | 0.0168 (2) | |
C9 | 0.35054 (14) | 0.39082 (11) | 0.17701 (7) | 0.0163 (2) | |
H9A | 0.2528 | 0.3399 | 0.1719 | 0.020* | |
H9B | 0.4335 | 0.3382 | 0.2012 | 0.020* | |
C10 | 0.17458 (14) | 0.55668 (11) | 0.23059 (7) | 0.0171 (2) | |
H10A | 0.0746 | 0.5263 | 0.2134 | 0.021* | |
C11 | 0.20643 (14) | 0.66705 (11) | 0.26741 (7) | 0.0172 (2) | |
C12 | 0.43050 (13) | 0.57897 (11) | 0.25673 (6) | 0.01558 (19) | |
C13 | 0.38107 (18) | 0.19047 (14) | −0.08367 (7) | 0.0267 (3) | |
H13A | 0.3421 | 0.2744 | −0.0969 | 0.040* | |
H13B | 0.3378 | 0.1290 | −0.1198 | 0.040* | |
H13C | 0.4974 | 0.1894 | −0.0862 | 0.040* | |
C14 | 0.60238 (15) | 0.54790 (13) | 0.26074 (8) | 0.0226 (2) | |
H14A | 0.6556 | 0.6059 | 0.2959 | 0.034* | |
H14B | 0.6494 | 0.5557 | 0.2098 | 0.034* | |
H14C | 0.6155 | 0.4616 | 0.2792 | 0.034* | |
H1N2 | 0.436 (2) | 0.3704 (17) | 0.0004 (12) | 0.028 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.03837 (9) | 0.01604 (7) | 0.03988 (9) | −0.00786 (5) | −0.01265 (6) | 0.00296 (5) |
O1 | 0.0347 (5) | 0.0166 (4) | 0.0195 (4) | −0.0089 (4) | 0.0077 (4) | −0.0024 (3) |
O2 | 0.0300 (5) | 0.0167 (4) | 0.0342 (5) | 0.0039 (3) | 0.0041 (4) | −0.0044 (4) |
O3 | 0.0162 (4) | 0.0334 (6) | 0.0537 (7) | 0.0041 (4) | 0.0052 (4) | −0.0103 (5) |
N1 | 0.0189 (4) | 0.0138 (4) | 0.0179 (4) | −0.0020 (3) | 0.0007 (3) | −0.0014 (3) |
N2 | 0.0244 (5) | 0.0161 (4) | 0.0162 (4) | −0.0052 (4) | 0.0044 (4) | −0.0017 (4) |
N3 | 0.0153 (4) | 0.0130 (4) | 0.0160 (4) | −0.0008 (3) | 0.0029 (3) | −0.0008 (3) |
N4 | 0.0176 (4) | 0.0152 (4) | 0.0189 (4) | 0.0000 (3) | 0.0009 (4) | −0.0017 (3) |
N5 | 0.0204 (5) | 0.0181 (5) | 0.0261 (5) | 0.0030 (4) | 0.0068 (4) | 0.0003 (4) |
C1 | 0.0245 (6) | 0.0194 (5) | 0.0222 (5) | 0.0008 (4) | −0.0012 (5) | −0.0056 (4) |
C2 | 0.0272 (6) | 0.0159 (5) | 0.0291 (6) | 0.0019 (5) | −0.0055 (5) | −0.0065 (5) |
C3 | 0.0255 (6) | 0.0147 (5) | 0.0284 (6) | −0.0028 (4) | −0.0095 (5) | 0.0003 (4) |
C4 | 0.0241 (6) | 0.0183 (5) | 0.0212 (5) | −0.0036 (4) | −0.0030 (4) | 0.0009 (4) |
C5 | 0.0213 (5) | 0.0156 (5) | 0.0183 (5) | −0.0013 (4) | −0.0020 (4) | −0.0024 (4) |
C6 | 0.0201 (5) | 0.0149 (5) | 0.0192 (5) | −0.0007 (4) | −0.0024 (4) | −0.0030 (4) |
C7 | 0.0200 (5) | 0.0168 (5) | 0.0176 (5) | −0.0017 (4) | 0.0007 (4) | −0.0028 (4) |
C8 | 0.0182 (5) | 0.0154 (5) | 0.0168 (5) | −0.0018 (4) | 0.0030 (4) | −0.0012 (4) |
C9 | 0.0199 (5) | 0.0116 (4) | 0.0175 (5) | −0.0016 (4) | 0.0035 (4) | −0.0016 (4) |
C10 | 0.0145 (5) | 0.0167 (5) | 0.0201 (5) | −0.0011 (4) | 0.0033 (4) | 0.0007 (4) |
C11 | 0.0172 (5) | 0.0148 (5) | 0.0197 (5) | 0.0011 (4) | 0.0040 (4) | −0.0004 (4) |
C12 | 0.0165 (5) | 0.0140 (4) | 0.0163 (5) | −0.0002 (4) | 0.0002 (4) | −0.0004 (4) |
C13 | 0.0371 (7) | 0.0252 (6) | 0.0178 (5) | −0.0095 (5) | 0.0034 (5) | −0.0032 (5) |
C14 | 0.0162 (5) | 0.0221 (6) | 0.0296 (6) | 0.0026 (4) | −0.0041 (5) | −0.0036 (5) |
Br1—C3 | 1.8962 (13) | C3—C4 | 1.3919 (19) |
O1—C8 | 1.2302 (14) | C4—C5 | 1.3912 (17) |
O2—N5 | 1.2310 (15) | C4—H4A | 0.9500 |
O3—N5 | 1.2363 (15) | C5—C6 | 1.3989 (17) |
N1—C7 | 1.2901 (15) | C5—H5A | 0.9500 |
N1—N2 | 1.3783 (14) | C6—C7 | 1.4824 (17) |
N2—C8 | 1.3483 (15) | C7—C13 | 1.5102 (18) |
N2—H1N2 | 0.81 (2) | C8—C9 | 1.5190 (16) |
N3—C10 | 1.3614 (15) | C9—H9A | 0.9900 |
N3—C12 | 1.3779 (15) | C9—H9B | 0.9900 |
N3—C9 | 1.4554 (15) | C10—C11 | 1.3671 (17) |
N4—C12 | 1.3223 (15) | C10—H10A | 0.9500 |
N4—C11 | 1.3644 (16) | C12—C14 | 1.4857 (16) |
N5—C11 | 1.4264 (15) | C13—H13A | 0.9800 |
C1—C2 | 1.3898 (19) | C13—H13B | 0.9800 |
C1—C6 | 1.3992 (17) | C13—H13C | 0.9800 |
C1—H1A | 0.9500 | C14—H14A | 0.9800 |
C2—C3 | 1.383 (2) | C14—H14B | 0.9800 |
C2—H2A | 0.9500 | C14—H14C | 0.9800 |
C7—N1—N2 | 116.91 (10) | C6—C7—C13 | 119.67 (10) |
C8—N2—N1 | 119.67 (10) | O1—C8—N2 | 121.89 (11) |
C8—N2—H1N2 | 117.7 (13) | O1—C8—C9 | 120.65 (10) |
N1—N2—H1N2 | 122.6 (13) | N2—C8—C9 | 117.44 (10) |
C10—N3—C12 | 107.86 (9) | N3—C9—C8 | 109.07 (9) |
C10—N3—C9 | 124.22 (10) | N3—C9—H9A | 109.9 |
C12—N3—C9 | 126.68 (10) | C8—C9—H9A | 109.9 |
C12—N4—C11 | 103.86 (10) | N3—C9—H9B | 109.9 |
O2—N5—O3 | 123.61 (11) | C8—C9—H9B | 109.9 |
O2—N5—C11 | 119.47 (11) | H9A—C9—H9B | 108.3 |
O3—N5—C11 | 116.91 (11) | N3—C10—C11 | 104.02 (10) |
C2—C1—C6 | 121.13 (12) | N3—C10—H10A | 128.0 |
C2—C1—H1A | 119.4 | C11—C10—H10A | 128.0 |
C6—C1—H1A | 119.4 | N4—C11—C10 | 112.94 (10) |
C3—C2—C1 | 118.82 (12) | N4—C11—N5 | 122.29 (11) |
C3—C2—H2A | 120.6 | C10—C11—N5 | 124.74 (11) |
C1—C2—H2A | 120.6 | N4—C12—N3 | 111.32 (10) |
C2—C3—C4 | 121.70 (12) | N4—C12—C14 | 125.61 (11) |
C2—C3—Br1 | 118.46 (10) | N3—C12—C14 | 123.07 (10) |
C4—C3—Br1 | 119.80 (11) | C7—C13—H13A | 109.5 |
C5—C4—C3 | 118.74 (12) | C7—C13—H13B | 109.5 |
C5—C4—H4A | 120.6 | H13A—C13—H13B | 109.5 |
C3—C4—H4A | 120.6 | C7—C13—H13C | 109.5 |
C4—C5—C6 | 120.96 (11) | H13A—C13—H13C | 109.5 |
C4—C5—H5A | 119.5 | H13B—C13—H13C | 109.5 |
C6—C5—H5A | 119.5 | C12—C14—H14A | 109.5 |
C5—C6—C1 | 118.63 (11) | C12—C14—H14B | 109.5 |
C5—C6—C7 | 120.95 (11) | H14A—C14—H14B | 109.5 |
C1—C6—C7 | 120.41 (11) | C12—C14—H14C | 109.5 |
N1—C7—C6 | 115.78 (11) | H14A—C14—H14C | 109.5 |
N1—C7—C13 | 124.54 (11) | H14B—C14—H14C | 109.5 |
C7—N1—N2—C8 | 176.66 (12) | C12—N3—C9—C8 | −73.37 (14) |
C6—C1—C2—C3 | 0.25 (19) | O1—C8—C9—N3 | 18.68 (16) |
C1—C2—C3—C4 | −1.2 (2) | N2—C8—C9—N3 | −162.77 (10) |
C1—C2—C3—Br1 | 176.42 (10) | C12—N3—C10—C11 | −0.47 (13) |
C2—C3—C4—C5 | 1.3 (2) | C9—N3—C10—C11 | −168.42 (10) |
Br1—C3—C4—C5 | −176.37 (9) | C12—N4—C11—C10 | 0.27 (14) |
C3—C4—C5—C6 | −0.28 (19) | C12—N4—C11—N5 | −178.11 (11) |
C4—C5—C6—C1 | −0.66 (18) | N3—C10—C11—N4 | 0.13 (14) |
C4—C5—C6—C7 | 178.40 (11) | N3—C10—C11—N5 | 178.47 (11) |
C2—C1—C6—C5 | 0.68 (19) | O2—N5—C11—N4 | −0.47 (18) |
C2—C1—C6—C7 | −178.39 (12) | O3—N5—C11—N4 | 178.49 (12) |
N2—N1—C7—C6 | −178.98 (10) | O2—N5—C11—C10 | −178.65 (12) |
N2—N1—C7—C13 | 0.29 (18) | O3—N5—C11—C10 | 0.30 (19) |
C5—C6—C7—N1 | 24.91 (17) | C11—N4—C12—N3 | −0.58 (13) |
C1—C6—C7—N1 | −156.05 (12) | C11—N4—C12—C14 | −179.49 (12) |
C5—C6—C7—C13 | −154.40 (12) | C10—N3—C12—N4 | 0.69 (13) |
C1—C6—C7—C13 | 24.64 (18) | C9—N3—C12—N4 | 168.26 (11) |
N1—N2—C8—O1 | −178.13 (11) | C10—N3—C12—C14 | 179.63 (11) |
N1—N2—C8—C9 | 3.34 (17) | C9—N3—C12—C14 | −12.80 (18) |
C10—N3—C9—C8 | 92.28 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.81 (2) | 2.04 (2) | 2.8318 (14) | 166.6 (18) |
C9—H9A···O3ii | 0.99 | 2.31 | 3.1818 (16) | 147 |
C9—H9B···N4iii | 0.99 | 2.40 | 3.3462 (16) | 160 |
C10—H10A···O2ii | 0.95 | 2.56 | 3.4488 (16) | 155 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, y−1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H14BrN5O3 |
Mr | 380.21 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 8.4176 (1), 10.6541 (1), 17.4933 (2) |
β (°) | 90.100 (1) |
V (Å3) | 1568.83 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.64 |
Crystal size (mm) | 0.37 × 0.33 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.441, 0.701 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 45099, 6320, 5026 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.784 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.082, 1.02 |
No. of reflections | 6320 |
No. of parameters | 214 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.88, −0.66 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.81 (2) | 2.04 (2) | 2.8318 (14) | 166.6 (18) |
C9—H9A···O3ii | 0.9900 | 2.3100 | 3.1818 (16) | 147.00 |
C9—H9B···N4iii | 0.9900 | 2.4000 | 3.3462 (16) | 160.00 |
C10—H10A···O2ii | 0.9500 | 2.5600 | 3.4488 (16) | 155.00 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, y−1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2. |
Acknowledgements
The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for an Incentive Grant.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chu, T., Hu, S., Wei, B., Wang, Y., Liu, X. & Wang, X. (2004). Bioorg. Med. Chem. 14, 747–749. CrossRef CAS Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Khalafi-Nezhad, A., Rad, M. N. S., Mohabatkar, H., Asrari, Z. & Hemmateenejad, B. (2005). Bioorg. Med. Chem. 13, 1931–1938. Web of Science PubMed CAS Google Scholar
Krapcho, J. & Turk, C. F. (1966). J. Med. Chem. 9, 191–195. CrossRef CAS PubMed Web of Science Google Scholar
Priya, V. F. & Kalluraya, B. (2005). Indian J. Chem. Sect. B, 44, 1456–1459. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The chemistry of imidazole derivatives has been the subject of much interest due to their importance in various applications and also due to their widespread potential as well as proven biological and pharmacological activities (Priya & Kalluraya, 2005). Various applications of imidazoles have been listed in the literature with functions as widely divergent as antidepressant agents (Krapcho & Turk, 1966), as a marker for imaging tumor hypoxia( Chu et al., 2004), and in antibacterial activity (Khalafi-Nezhad et al., 2005). In view of the obvious importance of imidazole derivatives as potential pharmacological agents, herein we report the crystal structure of the above imidazole derivative.
In the title molecule, Fig. 1, the mean plane of the imidazole ring (N3/N4/C10-C12, r.m.s deviation = 0.004 Å) forms a dihedral angle of 58.13 (7)° with the phenyl ring (C1-C6). Bond lengths (Allen et al., 1987) and angles are within normal ranges. A short Br1···Br1 contact of 3.4932 (2) Å also occurs. In the crystal (Fig. 2), molecules are linked via intermolecular N2–H1N2···O1, C9–H9A···O3, C9–H9B···N4 and C10–H10A···O2 hydrogen bonds (Table 1) into a three-dimensional network.