N′-[(E)-1-(4-Bromo­phen­yl)ethyl­idene]-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide

Fun, H.-K.; Quah, C.K.; Frank, P.V.; Damodara, N.; Kalluraya, B.

doi:10.1107/S160053681202795X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2192

https://doi.org/10.1107/S160053681202795X

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N′-[(E)-1-(4-Bromophenyl)ethylidene]-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Priya V. Frank,^b,^c N. Damodara ^c and Balakrishna Kalluraya ^b

^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

(Received 11 June 2012; accepted 20 June 2012; online 23 June 2012)

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

C₁₄H₁₄BrN₅O₃
M_r = 380.21
Monoclinic, P 2₁ /c
a = 8.4176 (1) Å
b = 10.6541 (1) Å
c = 17.4933 (2) Å
β = 90.100 (1)°
V = 1568.83 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.64 mm⁻¹
T = 100 K
0.37 × 0.33 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.441, T_max = 0.701
45099 measured reflections
6320 independent reflections
5026 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.082
S = 1.02
6320 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681202795X/rz2774sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

N'-[(E)-1-(4-Bromophenyl)ethylidene]-2-(2-methyl-4-nitro- 1H-imidazol-1-yl)acetohydrazide top

Crystal data top

C₁₄H₁₄BrN₅O₃	F(000) = 768
M_r = 380.21	D_x = 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

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6320 independent reflections
Radiation source: fine-focus sealed tube	5026 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 33.9°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.441, T_max = 0.701	k = −16→16
45099 measured reflections	l = −27→27

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)] = 0.032	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(F_o²) + (0.0423P)² + 0.4612P] where P = (F_o² + 2F_c²)/3
6320 reflections	(Δ/σ)_max = 0.001
214 parameters	Δρ_max = 0.88 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₁₄H₁₄BrN₅O₃	V = 1568.83 (3) Å³
M_r = 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)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6320 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5026 reflections with I > 2σ(I)
T_min = 0.441, T_max = 0.701	R_int = 0.040
45099 measured reflections

Refinement top

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	Δρ_max = 0.88 e Å⁻³
6320 reflections	Δρ_min = −0.66 e Å⁻³
214 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.441, 0.701
No. of measured, independent and observed [I > 2σ(I)] reflections	45099, 6320, 5026
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.66

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

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.

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