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Acta Cryst. (2009). E65, o1184-o1185    [ doi:10.1107/S1600536809015542 ]

N'-[(E)-4-Bromobenzylidene]-2-(4-isobutylphenyl)propanohydrazide

H.-K. Fun, C. K. Quah, K. V. Sujith and B. Kalluraya

Abstract top

The asymmetric unit of the title compound, C20H23BrN2O, contains two independent molecules (A and B), in which the orientations of the 4-isobutylphenyl units are different. The dihedral angle between the two benzene rings is 88.45 (8)° in molecule A and 89.87 (8)° in molecule B. Molecules A and B are linked by a C-H...N hydrogen bond. In the crystal, molecules are linked into chains running along the a axis by intermolcular N-H...O and C-H...O hydrogen bonds. The crystal structure is further stabilized by C-H...[pi] interactions. The presence of pseudosymmetry in the structure suggests the higher symmetry space group Pbca. However, attempts to refine the structure in this space group resulted in a disorder model with high R (0.097) and wR (0.257) values. The crystal studied was an inversion twin with a 0.595 (4):0.405 (4) domain ratio.

Comment top

Hydrazones have been found to possess antimicrobial, anticonvulsant, analgesic, antiinflammatory, antiplatelet, antitubercular, anticancer and antitumoral activities (Bedia et al., 2006; Rollas et al., 2002; Terzioglu & Gürsoy, 2003). Aryl hydrazones are important building blocks for the synthesis of a variety of heterocyclic compounds such as pyrazolines and pyrazoles (Sridhar et al., 2003). Aryl hydrazones have been most conveniently synthesized by the reaction of aryl hydrazines with carbonyl compounds. Similarly ibuprofen is also known for their pharmaceutical activities and belongs to the class of Non-Steroidal Anti-Inflammatory Drugs (Amir & Kumar, 2007). We are interested in the synthesis and crystal structure of ibuprofen containing hydrazone derivatives (Fun et al., 2008). Prompted by these observations, it was contemplated to synthesize and report the crystal structure of the title compound.

The asymmetric unit contains two independent molecules (Fig. 1), A and B, in which the orientations of the 4-isobutylphenyl units are different (Table 1). The bond lengths (Allen et al., 1987) and angles in the molecule (Fig. 1) are within normal ranges and are comparable to a closely related structure (Fun et al., 2008). The molecule A is linked to the molecule B by C20B—H20F···N1A hydrogen bond (Fig. 1). The dihedral angle formed by the C1A-C6A and C10A-C15A benzene rings is 89.87 (8)° and that between the C1B-C6B and C10B-C15B planes is 88.45 (8)°, indicating that they are almost perpendicular to each other.

The crystal packing is consolidated by intermolecular N—H···O and C—H···O hydrogen bonds (Fig. 2) which link the independent molecules into chains parallel to the [100]. The crystal structure is further stabilized by C—H···π interactions (Table 1) involving the C1A-C6A (centroid Cg1) and C1B–C6B (centroid Cg2) benzene rings.

Related literature top

For the biological activities of hydrazone derivatives, see: Bedia et al. (2006); Rollas et al. (2002); Terzioglu & Gürsoy (2003); Sridhar et al. (2003); Amir & Kumar (2007). For a related structure, see: Fun et al. (2008). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1 and Cg2 are the centroids of the C1A--C6A and C1B–C6B benzene rings, respectively.

Experimental top

The title compound was obtained by refluxing a mixture of 2-[4-(2-methylpropyl)phenyl]propanehydrazide (0.01 mol), 4-bromobenzaldehyde (0.01 mol) in ethanol (30 ml) and 3 drops of concentrated sulfuric acid for 1 h. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with ethanol and dried. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol-N,N-dimethylformamide (DMF) (3:1) solution.

Refinement top

Atoms H1NA and H1NB were located in a difference difference Fourier map and refined freely. The remaining H atoms were positioned geometrically and refined using a riding model, with C-H = 0.93–0.98 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for the methyl groups. The presence of pseudo-symmetry in the structure suggests a higher symmetry space group Pbca. But attempts to refine the structure in the space group Pbca resulted in a disorder model with high R (0.097) and wR (0.257) values. Because of the presence of a pseudo-centre of symmetry, the absolute structure could not be determined. The reported Flack parameter was obtained by TWIN/BASF procedure in SHELXL (Sheldrick, 2008).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. The dashed line indicates a hydrogen bond.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the a axis. Intermolecular interactions are shown as dashed lines.
N'-[(E)-4-Bromobenzylidene]-2-(4-isobutylphenyl)propanohydrazide top
Crystal data top
C20H23BrN2OF000 = 1600
Mr = 387.31Dx = 1.396 Mg m−3
Orthorhombic, P212121Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9400 reflections
a = 9.1440 (1) Åθ = 2.5–31.7º
b = 12.0110 (1) ŵ = 2.24 mm−1
c = 33.5670 (4) ÅT = 100 K
V = 3686.62 (7) Å3Block, colourless
Z = 80.49 × 0.38 × 0.19 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		20557 independent reflections
Radiation source: fine-focus sealed tube13317 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.045
T = 100 Kθmax = 38.6º
φ and ω scansθmin = 1.2º
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −16→16
Tmin = 0.407, Tmax = 0.682k = −21→20
120355 measured reflectionsl = −58→56
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042  w = 1/[σ2(Fo2) + (0.0498P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.72 e Å−3
20557 reflectionsΔρmin = −0.61 e Å−3
448 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 9205 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.595 (4)
Crystal data top
C20H23BrN2OV = 3686.62 (7) Å3
Mr = 387.31Z = 8
Orthorhombic, P212121Mo Kα
a = 9.1440 (1) ŵ = 2.24 mm−1
b = 12.0110 (1) ÅT = 100 K
c = 33.5670 (4) Å0.49 × 0.38 × 0.19 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		20557 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		13317 reflections with I > 2σ(I)
Tmin = 0.407, Tmax = 0.682Rint = 0.045
120355 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.103Δρmax = 0.72 e Å−3
S = 1.04Δρmin = −0.61 e Å−3
20557 reflectionsAbsolute structure: Flack (1983), 9205 Friedel pairs
448 parametersFlack parameter: 0.595 (4)
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br1A0.849271 (19)0.479672 (14)0.078235 (6)0.02563 (4)
O1A0.88325 (12)1.00346 (11)0.27706 (3)0.0213 (2)
N1A0.73139 (15)0.87330 (12)0.22421 (4)0.0173 (3)
N2A0.66653 (15)0.94990 (12)0.24939 (4)0.0164 (3)
C1A0.81210 (19)0.67440 (14)0.17959 (5)0.0184 (3)
H1AA0.86010.68130.20390.022*
C2A0.85669 (18)0.59430 (13)0.15259 (5)0.0187 (3)
H2AA0.93280.54600.15890.022*
C3A0.78674 (19)0.58675 (14)0.11603 (5)0.0189 (3)
C4A0.6703 (2)0.65496 (14)0.10623 (5)0.0211 (3)
H4AA0.62430.64870.08160.025*
C5A0.62366 (19)0.73315 (14)0.13401 (5)0.0192 (3)
H5AA0.54370.77810.12810.023*
C6A0.6946 (2)0.74535 (13)0.17050 (5)0.0165 (3)
C7A0.64467 (19)0.83222 (13)0.19787 (5)0.0176 (3)
H7AA0.54900.85810.19620.021*
C8A0.74894 (16)1.00775 (15)0.27548 (5)0.0170 (3)
C9A0.65950 (18)1.07453 (13)0.30584 (5)0.0172 (3)
H9AA0.56241.08880.29460.021*
C10A0.64245 (16)0.99942 (13)0.34220 (4)0.0155 (3)
C11A0.51587 (18)0.93583 (14)0.34705 (5)0.0185 (3)
H11A0.43970.94280.32890.022*
C12A0.50265 (19)0.86228 (13)0.37874 (5)0.0182 (3)
H12A0.41670.82170.38170.022*
C13A0.61539 (18)0.84797 (13)0.40622 (4)0.0172 (3)
C14A0.74046 (17)0.91272 (14)0.40148 (5)0.0204 (3)
H14A0.81670.90560.41960.025*
C15A0.75390 (17)0.98781 (15)0.37016 (5)0.0200 (3)
H15A0.83821.03070.36790.024*
C16A0.60190 (19)0.76581 (13)0.43996 (5)0.0194 (3)
H16A0.69910.75080.45020.023*
H16B0.56400.69650.42930.023*
C17A0.50438 (19)0.80147 (14)0.47485 (5)0.0219 (3)
H17A0.40350.80640.46520.026*
C18A0.5468 (3)0.91335 (16)0.49144 (6)0.0442 (6)
H18A0.53410.96930.47130.066*
H18B0.64730.91160.49970.066*
H18C0.48590.93050.51390.066*
C19A0.5104 (2)0.71186 (15)0.50728 (5)0.0274 (4)
H19A0.44770.73280.52900.041*
H19B0.60900.70460.51680.041*
H19C0.47840.64200.49640.041*
C20A0.73368 (19)1.18646 (15)0.31432 (6)0.0229 (4)
H20A0.68761.22120.33680.034*
H20B0.72461.23390.29140.034*
H20C0.83531.17440.32000.034*
Br1B0.63994 (2)−0.015149 (14)0.077318 (5)0.02449 (4)
O1B0.61864 (12)0.49983 (11)0.27805 (3)0.0206 (2)
N1B0.77028 (15)0.36554 (11)0.22662 (4)0.0161 (3)
N2B0.83490 (16)0.44565 (12)0.25061 (4)0.0165 (3)
C1B0.68109 (19)0.17270 (13)0.18046 (5)0.0175 (3)
H1BA0.63140.18090.20450.021*
C2B0.63144 (18)0.09615 (13)0.15256 (5)0.0183 (3)
H2BA0.54920.05290.15770.022*
C3B0.7075 (2)0.08541 (13)0.11670 (5)0.0190 (3)
C4B0.83235 (19)0.14694 (13)0.10867 (5)0.0190 (3)
H4BA0.88240.13790.08480.023*
C5B0.88101 (19)0.22226 (13)0.13705 (5)0.0180 (3)
H5BA0.96540.26330.13230.022*
C6B0.8045 (2)0.23731 (13)0.17286 (5)0.0164 (3)
C7B0.85619 (19)0.32373 (13)0.20041 (5)0.0175 (3)
H7BA0.95240.34840.19880.021*
C8B0.75320 (16)0.50621 (14)0.27594 (4)0.0153 (3)
C9B0.84083 (18)0.58372 (12)0.30309 (4)0.0144 (3)
H9BA0.93710.59570.29100.017*
C10B0.86268 (16)0.52286 (12)0.34255 (4)0.0146 (3)
C11B0.96862 (18)0.43906 (13)0.34546 (5)0.0165 (3)
H11B1.02610.42190.32340.020*
C12B0.98872 (19)0.38154 (13)0.38080 (5)0.0188 (3)
H12B1.06010.32650.38210.023*
C13B0.90454 (18)0.40422 (13)0.41439 (5)0.0182 (3)
C14B0.80027 (18)0.48834 (14)0.41132 (5)0.0205 (3)
H14B0.74330.50560.43340.025*
C15B0.77918 (18)0.54699 (13)0.37620 (5)0.0182 (3)
H15B0.70880.60280.37510.022*
C16B0.9216 (2)0.33528 (14)0.45152 (5)0.0215 (3)
H16C0.87400.37330.47350.026*
H16D1.02480.32930.45790.026*
C17B0.85697 (19)0.21766 (13)0.44763 (5)0.0195 (3)
H17B0.90580.18060.42530.023*
C18B0.8867 (2)0.14987 (15)0.48509 (5)0.0313 (4)
H18D0.84880.07590.48170.047*
H18E0.83990.18470.50750.047*
H18F0.99020.14630.48970.047*
C19B0.6939 (2)0.22087 (16)0.43873 (6)0.0285 (4)
H19D0.65840.14640.43500.043*
H19E0.67710.26340.41490.043*
H19F0.64320.25490.46060.043*
C20B0.76379 (18)0.69647 (14)0.30640 (5)0.0190 (3)
H20D0.81300.74160.32580.029*
H20E0.66410.68530.31440.029*
H20F0.76590.73320.28100.029*
H1NA0.568 (2)0.9602 (19)0.2475 (6)0.034 (6)*
H1NB0.918 (2)0.4564 (18)0.2501 (6)0.022 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.02409 (8)0.02207 (8)0.03074 (9)0.00076 (7)0.00373 (8)−0.00849 (8)
O1A0.0144 (5)0.0287 (6)0.0207 (5)0.0038 (5)0.0014 (5)−0.0010 (5)
N1A0.0173 (7)0.0183 (6)0.0162 (7)0.0044 (6)0.0033 (5)0.0026 (5)
N2A0.0131 (6)0.0205 (6)0.0155 (6)0.0042 (6)0.0016 (5)−0.0004 (5)
C1A0.0171 (8)0.0192 (7)0.0188 (8)0.0012 (7)−0.0003 (7)0.0027 (6)
C2A0.0161 (8)0.0172 (7)0.0228 (8)0.0033 (7)0.0031 (7)0.0018 (6)
C3A0.0178 (8)0.0179 (7)0.0209 (8)−0.0027 (7)0.0042 (7)−0.0021 (6)
C4A0.0196 (8)0.0222 (8)0.0216 (8)0.0005 (7)−0.0010 (7)−0.0018 (6)
C5A0.0159 (8)0.0193 (7)0.0225 (8)0.0028 (7)−0.0008 (7)0.0008 (6)
C6A0.0152 (9)0.0174 (7)0.0169 (8)0.0003 (6)0.0018 (6)0.0015 (6)
C7A0.0162 (8)0.0176 (7)0.0190 (7)0.0044 (7)0.0014 (7)0.0004 (6)
C8A0.0170 (7)0.0194 (8)0.0146 (7)0.0024 (7)0.0025 (6)0.0047 (6)
C9A0.0137 (7)0.0185 (7)0.0194 (7)0.0033 (7)0.0019 (6)0.0010 (6)
C10A0.0143 (7)0.0179 (6)0.0144 (6)0.0015 (6)0.0024 (5)−0.0011 (5)
C11A0.0153 (7)0.0213 (8)0.0188 (8)−0.0011 (6)−0.0001 (6)−0.0003 (6)
C12A0.0180 (8)0.0182 (7)0.0185 (8)−0.0042 (6)0.0003 (6)−0.0019 (6)
C13A0.0183 (7)0.0173 (6)0.0160 (7)−0.0005 (6)0.0027 (6)−0.0021 (5)
C14A0.0160 (7)0.0293 (8)0.0160 (7)−0.0025 (7)−0.0004 (6)0.0036 (6)
C15A0.0133 (7)0.0284 (8)0.0184 (7)−0.0060 (7)−0.0002 (5)0.0019 (6)
C16A0.0206 (8)0.0173 (7)0.0203 (7)0.0020 (6)0.0031 (6)0.0025 (6)
C17A0.0228 (8)0.0232 (8)0.0197 (8)0.0028 (7)0.0051 (6)0.0041 (6)
C18A0.0875 (18)0.0250 (9)0.0202 (9)0.0014 (11)0.0156 (11)−0.0014 (7)
C19A0.0312 (10)0.0280 (9)0.0231 (8)−0.0014 (8)0.0046 (7)0.0094 (7)
C20A0.0222 (9)0.0197 (8)0.0269 (9)0.0020 (7)0.0041 (7)0.0033 (7)
Br1B0.03377 (10)0.01815 (7)0.02155 (8)0.00059 (7)−0.00595 (8)−0.00540 (7)
O1B0.0119 (5)0.0290 (6)0.0210 (5)−0.0029 (5)0.0010 (4)−0.0038 (5)
N1B0.0165 (6)0.0165 (6)0.0153 (6)−0.0018 (6)−0.0010 (5)−0.0015 (5)
N2B0.0129 (7)0.0206 (7)0.0160 (6)−0.0039 (6)0.0007 (5)−0.0023 (5)
C1B0.0196 (9)0.0174 (7)0.0154 (7)0.0001 (7)0.0008 (7)0.0005 (6)
C2B0.0186 (8)0.0163 (6)0.0200 (7)0.0002 (7)−0.0004 (7)0.0016 (6)
C3B0.0249 (8)0.0126 (6)0.0194 (8)0.0011 (7)−0.0037 (7)−0.0018 (6)
C4B0.0222 (8)0.0185 (7)0.0161 (7)0.0041 (7)−0.0001 (7)−0.0011 (6)
C5B0.0189 (8)0.0185 (7)0.0167 (7)0.0014 (7)0.0005 (6)0.0007 (6)
C6B0.0171 (9)0.0157 (7)0.0166 (8)0.0021 (6)−0.0024 (6)−0.0007 (6)
C7B0.0171 (8)0.0192 (7)0.0163 (7)0.0002 (7)−0.0012 (6)−0.0005 (6)
C8B0.0167 (7)0.0160 (7)0.0132 (7)−0.0022 (6)0.0009 (5)0.0009 (6)
C9B0.0145 (7)0.0150 (6)0.0135 (6)−0.0022 (6)0.0000 (6)0.0007 (5)
C10B0.0143 (7)0.0139 (6)0.0157 (6)−0.0014 (6)−0.0014 (5)−0.0005 (5)
C11B0.0162 (7)0.0173 (7)0.0160 (7)0.0007 (6)0.0015 (6)−0.0022 (6)
C12B0.0172 (8)0.0146 (6)0.0245 (8)0.0023 (6)−0.0027 (6)−0.0005 (6)
C13B0.0213 (7)0.0173 (6)0.0160 (7)−0.0021 (6)−0.0030 (6)0.0005 (5)
C14B0.0255 (8)0.0221 (7)0.0139 (6)0.0036 (7)0.0012 (6)0.0000 (6)
C15B0.0180 (7)0.0184 (7)0.0182 (7)0.0038 (6)0.0007 (6)−0.0006 (6)
C16B0.0285 (9)0.0212 (7)0.0148 (7)−0.0026 (7)−0.0066 (6)0.0023 (6)
C17B0.0236 (8)0.0190 (7)0.0159 (7)0.0002 (7)−0.0014 (6)0.0021 (5)
C18B0.0449 (12)0.0244 (8)0.0246 (9)−0.0040 (8)−0.0040 (8)0.0067 (7)
C19B0.0244 (9)0.0293 (9)0.0318 (9)−0.0033 (7)0.0007 (8)0.0004 (8)
C20B0.0224 (8)0.0166 (7)0.0180 (7)0.0015 (6)−0.0013 (6)0.0018 (6)
Geometric parameters (Å, °) top
Br1A—C3A1.8948 (17)Br1B—C3B1.8944 (16)
O1A—C8A1.2304 (19)O1B—C8B1.2349 (18)
N1A—C7A1.286 (2)N1B—C7B1.282 (2)
N1A—N2A1.3830 (18)N1B—N2B1.3868 (18)
N2A—C8A1.348 (2)N2B—C8B1.345 (2)
N2A—H1NA0.91 (2)N2B—H1NB0.770 (19)
C1A—C2A1.383 (2)C1B—C2B1.389 (2)
C1A—C6A1.405 (3)C1B—C6B1.393 (3)
C1A—H1AA0.93C1B—H1BA0.93
C2A—C3A1.387 (2)C2B—C3B1.396 (2)
C2A—H2AA0.93C2B—H2BA0.93
C3A—C4A1.383 (2)C3B—C4B1.386 (2)
C4A—C5A1.390 (2)C4B—C5B1.387 (2)
C4A—H4AA0.93C4B—H4BA0.93
C5A—C6A1.394 (2)C5B—C6B1.403 (2)
C5A—H5AA0.93C5B—H5BA0.93
C6A—C7A1.463 (2)C6B—C7B1.468 (2)
C7A—H7AA0.93C7B—H7BA0.93
C8A—C9A1.533 (2)C8B—C9B1.530 (2)
C9A—C10A1.526 (2)C9B—C10B1.526 (2)
C9A—C20A1.532 (2)C9B—C20B1.531 (2)
C9A—H9AA0.98C9B—H9BA0.98
C10A—C15A1.393 (2)C10B—C15B1.394 (2)
C10A—C11A1.396 (2)C10B—C11B1.400 (2)
C11A—C12A1.388 (2)C11B—C12B1.385 (2)
C11A—H11A0.93C11B—H11B0.93
C12A—C13A1.394 (2)C12B—C13B1.392 (2)
C12A—H12A0.93C12B—H12B0.93
C13A—C14A1.392 (2)C13B—C14B1.393 (2)
C13A—C16A1.507 (2)C13B—C16B1.505 (2)
C14A—C15A1.390 (2)C14B—C15B1.387 (2)
C14A—H14A0.93C14B—H14B0.93
C15A—H15A0.93C15B—H15B0.93
C16A—C17A1.533 (2)C16B—C17B1.537 (2)
C16A—H16A0.97C16B—H16C0.97
C16A—H16B0.97C16B—H16D0.97
C17A—C18A1.505 (3)C17B—C19B1.522 (3)
C17A—C19A1.532 (2)C17B—C18B1.523 (2)
C17A—H17A0.98C17B—H17B0.98
C18A—H18A0.96C18B—H18D0.96
C18A—H18B0.96C18B—H18E0.96
C18A—H18C0.96C18B—H18F0.96
C19A—H19A0.96C19B—H19D0.96
C19A—H19B0.96C19B—H19E0.96
C19A—H19C0.96C19B—H19F0.96
C20A—H20A0.96C20B—H20D0.96
C20A—H20B0.96C20B—H20E0.96
C20A—H20C0.96C20B—H20F0.96
C7A—N1A—N2A114.27 (13)C7B—N1B—N2B114.15 (13)
C8A—N2A—N1A120.01 (13)C8B—N2B—N1B120.36 (13)
C8A—N2A—H1NA121.9 (14)C8B—N2B—H1NB118.0 (16)
N1A—N2A—H1NA118.1 (14)N1B—N2B—H1NB121.7 (16)
C2A—C1A—C6A120.33 (16)C2B—C1B—C6B120.66 (15)
C2A—C1A—H1AA119.8C2B—C1B—H1BA119.7
C6A—C1A—H1AA119.8C6B—C1B—H1BA119.7
C1A—C2A—C3A119.30 (15)C1B—C2B—C3B118.66 (16)
C1A—C2A—H2AA120.3C1B—C2B—H2BA120.7
C3A—C2A—H2AA120.3C3B—C2B—H2BA120.7
C4A—C3A—C2A121.77 (15)C4B—C3B—C2B121.92 (15)
C4A—C3A—Br1A118.38 (13)C4B—C3B—Br1B118.22 (12)
C2A—C3A—Br1A119.85 (13)C2B—C3B—Br1B119.86 (13)
C3A—C4A—C5A118.49 (16)C3B—C4B—C5B118.57 (15)
C3A—C4A—H4AA120.8C3B—C4B—H4BA120.7
C5A—C4A—H4AA120.8C5B—C4B—H4BA120.7
C4A—C5A—C6A121.17 (16)C4B—C5B—C6B120.84 (16)
C4A—C5A—H5AA119.4C4B—C5B—H5BA119.6
C6A—C5A—H5AA119.4C6B—C5B—H5BA119.6
C5A—C6A—C1A118.87 (15)C1B—C6B—C5B119.29 (15)
C5A—C6A—C7A118.81 (16)C1B—C6B—C7B122.62 (15)
C1A—C6A—C7A122.32 (15)C5B—C6B—C7B118.06 (16)
N1A—C7A—C6A120.87 (16)N1B—C7B—C6B120.80 (16)
N1A—C7A—H7AA119.6N1B—C7B—H7BA119.6
C6A—C7A—H7AA119.6C6B—C7B—H7BA119.6
O1A—C8A—N2A124.37 (16)O1B—C8B—N2B123.79 (15)
O1A—C8A—C9A121.71 (15)O1B—C8B—C9B121.70 (15)
N2A—C8A—C9A113.78 (13)N2B—C8B—C9B114.50 (13)
C10A—C9A—C20A114.55 (13)C10B—C9B—C8B107.11 (12)
C10A—C9A—C8A106.07 (12)C10B—C9B—C20B114.91 (13)
C20A—C9A—C8A110.26 (14)C8B—C9B—C20B109.92 (13)
C10A—C9A—H9AA108.6C10B—C9B—H9BA108.2
C20A—C9A—H9AA108.6C8B—C9B—H9BA108.2
C8A—C9A—H9AA108.6C20B—C9B—H9BA108.2
C15A—C10A—C11A118.25 (14)C15B—C10B—C11B118.15 (14)
C15A—C10A—C9A121.57 (14)C15B—C10B—C9B122.14 (13)
C11A—C10A—C9A120.10 (14)C11B—C10B—C9B119.70 (13)
C12A—C11A—C10A120.65 (15)C12B—C11B—C10B120.68 (15)
C12A—C11A—H11A119.7C12B—C11B—H11B119.7
C10A—C11A—H11A119.7C10B—C11B—H11B119.7
C11A—C12A—C13A121.41 (15)C11B—C12B—C13B121.51 (15)
C11A—C12A—H12A119.3C11B—C12B—H12B119.2
C13A—C12A—H12A119.3C13B—C12B—H12B119.2
C14A—C13A—C12A117.58 (14)C12B—C13B—C14B117.42 (14)
C14A—C13A—C16A121.26 (15)C12B—C13B—C16B120.39 (15)
C12A—C13A—C16A121.16 (15)C14B—C13B—C16B122.10 (15)
C15A—C14A—C13A121.43 (15)C15B—C14B—C13B121.77 (15)
C15A—C14A—H14A119.3C15B—C14B—H14B119.1
C13A—C14A—H14A119.3C13B—C14B—H14B119.1
C14A—C15A—C10A120.65 (15)C14B—C15B—C10B120.47 (15)
C14A—C15A—H15A119.7C14B—C15B—H15B119.8
C10A—C15A—H15A119.7C10B—C15B—H15B119.8
C13A—C16A—C17A116.02 (13)C13B—C16B—C17B113.29 (13)
C13A—C16A—H16A108.3C13B—C16B—H16C108.9
C17A—C16A—H16A108.3C17B—C16B—H16C108.9
C13A—C16A—H16B108.3C13B—C16B—H16D108.9
C17A—C16A—H16B108.3C17B—C16B—H16D108.9
H16A—C16A—H16B107.4H16C—C16B—H16D107.7
C18A—C17A—C19A110.80 (15)C19B—C17B—C18B110.54 (15)
C18A—C17A—C16A112.47 (16)C19B—C17B—C16B111.74 (15)
C19A—C17A—C16A109.00 (14)C18B—C17B—C16B110.65 (13)
C18A—C17A—H17A108.1C19B—C17B—H17B107.9
C19A—C17A—H17A108.1C18B—C17B—H17B107.9
C16A—C17A—H17A108.1C16B—C17B—H17B107.9
C17A—C18A—H18A109.5C17B—C18B—H18D109.5
C17A—C18A—H18B109.5C17B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C17A—C18A—H18C109.5C17B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C17A—C19A—H19A109.5C17B—C19B—H19D109.5
C17A—C19A—H19B109.5C17B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C17A—C19A—H19C109.5C17B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C9A—C20A—H20A109.5C9B—C20B—H20D109.5
C9A—C20A—H20B109.5C9B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
C9A—C20A—H20C109.5C9B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
C7A—N1A—N2A—C8A−172.90 (15)C7B—N1B—N2B—C8B171.64 (15)
C6A—C1A—C2A—C3A1.7 (3)C6B—C1B—C2B—C3B−0.1 (2)
C1A—C2A—C3A—C4A−2.0 (3)C1B—C2B—C3B—C4B1.5 (2)
C1A—C2A—C3A—Br1A178.62 (12)C1B—C2B—C3B—Br1B−178.25 (12)
C2A—C3A—C4A—C5A0.3 (3)C2B—C3B—C4B—C5B−0.9 (2)
Br1A—C3A—C4A—C5A179.62 (13)Br1B—C3B—C4B—C5B178.82 (12)
C3A—C4A—C5A—C6A1.8 (3)C3B—C4B—C5B—C6B−1.0 (2)
C4A—C5A—C6A—C1A−2.1 (3)C2B—C1B—C6B—C5B−1.7 (2)
C4A—C5A—C6A—C7A177.39 (16)C2B—C1B—C6B—C7B176.39 (15)
C2A—C1A—C6A—C5A0.3 (3)C4B—C5B—C6B—C1B2.3 (2)
C2A—C1A—C6A—C7A−179.19 (15)C4B—C5B—C6B—C7B−175.90 (14)
N2A—N1A—C7A—C6A−176.44 (13)N2B—N1B—C7B—C6B179.61 (13)
C5A—C6A—C7A—N1A−155.46 (16)C1B—C6B—C7B—N1B−20.0 (2)
C1A—C6A—C7A—N1A24.0 (2)C5B—C6B—C7B—N1B158.13 (15)
N1A—N2A—C8A—O1A5.2 (3)N1B—N2B—C8B—O1B−4.2 (3)
N1A—N2A—C8A—C9A−170.40 (13)N1B—N2B—C8B—C9B174.74 (13)
O1A—C8A—C9A—C10A−82.77 (19)O1B—C8B—C9B—C10B82.66 (19)
N2A—C8A—C9A—C10A93.00 (16)N2B—C8B—C9B—C10B−96.26 (16)
O1A—C8A—C9A—C20A41.8 (2)O1B—C8B—C9B—C20B−42.8 (2)
N2A—C8A—C9A—C20A−142.45 (15)N2B—C8B—C9B—C20B138.28 (14)
C8A—C9A—C10A—C11A−96.54 (17)C8B—C9B—C10B—C11B77.53 (17)
C8A—C9A—C10A—C15A80.18 (18)C8B—C9B—C10B—C15B−101.83 (16)
C20A—C9A—C10A—C11A141.61 (15)C20B—C9B—C10B—C11B−160.06 (14)
C20A—C9A—C10A—C15A−41.7 (2)C20B—C9B—C10B—C15B20.6 (2)
C15A—C10A—C11A—C12A−0.6 (2)C15B—C10B—C11B—C12B0.4 (2)
C9A—C10A—C11A—C12A176.19 (15)C9B—C10B—C11B—C12B−178.97 (15)
C10A—C11A—C12A—C13A−1.1 (2)C10B—C11B—C12B—C13B0.4 (2)
C11A—C12A—C13A—C14A1.9 (2)C11B—C12B—C13B—C14B−0.9 (2)
C11A—C12A—C13A—C16A−178.41 (14)C11B—C12B—C13B—C16B175.84 (15)
C12A—C13A—C14A—C15A−1.0 (2)C12B—C13B—C14B—C15B0.6 (2)
C16A—C13A—C14A—C15A179.36 (15)C16B—C13B—C14B—C15B−176.03 (15)
C13A—C14A—C15A—C10A−0.8 (3)C13B—C14B—C15B—C10B0.1 (3)
C11A—C10A—C15A—C14A1.6 (2)C11B—C10B—C15B—C14B−0.7 (2)
C9A—C10A—C15A—C14A−175.20 (15)C9B—C10B—C15B—C14B178.71 (15)
C14A—C13A—C16A—C17A103.66 (19)C12B—C13B—C16B—C17B−72.7 (2)
C12A—C13A—C16A—C17A−76.0 (2)C14B—C13B—C16B—C17B103.90 (18)
C13A—C16A—C17A—C18A−53.4 (2)C13B—C16B—C17B—C19B−60.1 (2)
C13A—C16A—C17A—C19A−176.68 (15)C13B—C16B—C17B—C18B176.24 (16)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2A—H1NA···O1Bi0.91 (2)1.97 (2)2.830 (2)157 (2)
N2B—H1NB···O1Aii0.77 (2)2.11 (2)2.826 (2)155 (2)
C7A—H7AA···O1Bi0.932.453.241 (2)143
C7B—H7BA···O1Aii0.932.533.307 (3)141
C20B—H20F···N1A0.962.563.494 (2)164
C12A—H12A···Cg2i0.932.663.482 (2)148
C12B—H12B···Cg1ii0.932.793.680 (2)160
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+1/2.
Table 1
Selected geometric parameters (°) top
C8A—C9A—C10A—C11A−96.54 (17)C8B—C9B—C10B—C11B77.53 (17)
C8A—C9A—C10A—C15A80.18 (18)C8B—C9B—C10B—C15B−101.83 (16)
C20A—C9A—C10A—C11A141.61 (15)C20B—C9B—C10B—C11B−160.06 (14)
C20A—C9A—C10A—C15A−41.7 (2)C20B—C9B—C10B—C15B20.6 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2A—H1NA···O1Bi0.91 (2)1.97 (2)2.830 (2)157 (2)
N2B—H1NB···O1Aii0.77 (2)2.11 (2)2.826 (2)155 (2)
C7A—H7AA···O1Bi0.932.453.241 (2)143
C7B—H7BA···O1Aii0.932.533.307 (3)141
C20B—H20F···N1A0.962.563.494 (2)164
C12A—H12A···Cg2i0.932.663.482 (2)148
C12B—H12B···Cg1ii0.932.793.680 (2)160
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+1/2.
Acknowledgements top

HKF and CKQ acknowledge funding from the Malaysian Government and Universiti Sains Malaysia (USM) under the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CKQ thanks Universiti Sains Malaysia for a fellowship.

references
References top

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.

Amir, M. & Kumar, S. (2007). Acta Pharm. 57, 31–45.

Bedia, K.-K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253–1261.

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Fun, H.-K., Jebas, S. R., Sujith, K. V., Patil, P. S., Kalluraya, B. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o1001–o1002.

Rollas, S., Gülerman, N. & Erdeniz, H. (2002). Farmaco, 57, 171–174.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Sridhar, R. & Perumal, P. T. (2003). Synth. Commun. 33, 1483–1488.

Terzioglu, N. & Gürsoy, A. (2003). Eur. J. Med. Chem. 38, 781–786.