N′-(3,5-Dibromo-2-hy­droxy­benzyl­idene)-2-methyl­benzohydrazide

Tang, C.-B.

doi:10.1107/S1600536810048889

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3361

https://doi.org/10.1107/S1600536810048889

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N′-(3,5-Dibromo-2-hydroxybenzylidene)-2-methylbenzohydrazide

Chun-Bao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: tangchunbao@yahoo.com.cn

(Received 22 November 2010; accepted 23 November 2010; online 30 November 2010)

The asymmetric unit of the title compound, C₁₅H₁₂Br₂N₂O₂, contains two independent molecules in which the dihedral angles between the benzene rings are 49.5 (7) and 66.4 (7)°. Intramolecular O—H⋯N hydrogen bonds generate S(6) ring motifs in each molecule. In the crystal, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ); Pyta et al. (2010 ); Angelusiu et al. (2010 ). For related structures, see: Fun et al. (2008 ); Singh & Singh (2010 ); Ahmad et al. (2010 ); Tang (2010 ). For reference bond-length data, see: Allen et al. (1987 ) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₂Br₂N₂O₂
M_r = 412.09
Monoclinic, P 2₁ /c
a = 18.636 (3) Å
b = 9.606 (2) Å
c = 19.943 (3) Å
β = 113.726 (2)°
V = 3268.4 (10) Å³
Z = 8
Mo Kα radiation
μ = 4.97 mm⁻¹
T = 298 K
0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.486, T_max = 0.587
17117 measured reflections
6973 independent reflections
2208 reflections with I > 2σ(I)
R_int = 0.116

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.159
S = 0.89
6973 reflections
389 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4ⁱ	0.90 (1)	1.85 (2)	2.743 (8)	172 (7)
N4—H4⋯O2	0.90 (1)	1.92 (2)	2.815 (8)	174 (7)
O3—H3⋯N3	0.82	1.90	2.624 (8)	146
O1—H1⋯N1	0.82	1.87	2.584 (8)	145
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810048889/sj5065sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048889/sj5065Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds have received much attention in biological and structural chemistry in the last few years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010; Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010). In the present paper, the author reports the crystal structure of the new title hydrazone compound (Fig. 1).

The asymmetric unit of the title compound contains two independent molecules. The dihedral angles between the two benzene rings in the two molecules are 49.5 (7) and 66.4 (7)°, respectively. The torsion angles C1—C7—N1—N2, C7—N1—N2—C8, N1—N2—C8—C9, C15—C21—N3—N4, C21—N3—N4—C22, and N3—N4—C22—C23 are 3.9 (6), 4.3 (6), 1.8 (6), 2.4 (6), 7.3 (6), and 2.4 (6)°, respectively. Bond lengths in the molecules are normal (Allen et al., 1987) and comparable to those in the similar compound the author reported recently (Tang, 2010). Intramolecular O1—H1···N1 and O3—H3···N3 hydrogen bonds generate S(6) ring motifs in each molecule (Bernstein et al., 1995). In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the b axis (Fig. 2).

Related literature top

For general background to hydrazones, see: Rasras et al. (2010); Pyta et al. (2010); Angelusiu et al. (2010). For related structures, see: Fun et al. (2008); Singh & Singh (2010); Ahmad et al. (2010); Tang (2010). For reference bond-length data, see: Allen et al. (1987) and for hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

3,5-Dibromo-2-hydroxybenzaldehyde (0.1 mmol, 28.0 mg) and 2-methylbenzohydrazide (0.1 mmol, 15.0 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. Colourless block-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.

Structure description top

For general background to hydrazones, see: Rasras et al. (2010); Pyta et al. (2010); Angelusiu et al. (2010). For related structures, see: Fun et al. (2008); Singh & Singh (2010); Ahmad et al. (2010); Tang (2010). For reference bond-length data, see: Allen et al. (1987) and for hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Molecular packing of the title compound, with hydrogen bonds shown as dashed lines.

N'-(3,5-Dibromo-2-hydroxybenzylidene)-2-methylbenzohydrazide top

Crystal data top

C₁₅H₁₂Br₂N₂O₂	F(000) = 1616
M_r = 412.09	D_x = 1.675 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1348 reflections
a = 18.636 (3) Å	θ = 2.5–24.1°
b = 9.606 (2) Å	µ = 4.97 mm⁻¹
c = 19.943 (3) Å	T = 298 K
β = 113.726 (2)°	Block, colourless
V = 3268.4 (10) Å³	0.17 × 0.13 × 0.12 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	6973 independent reflections
Radiation source: fine-focus sealed tube	2208 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.116
ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→19
T_min = 0.486, T_max = 0.587	k = −12→11
17117 measured reflections	l = −25→25

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ²(F_o²)] where P = (F_o² + 2F_c²)/3
6973 reflections	(Δ/σ)_max < 0.001
389 parameters	Δρ_max = 0.32 e Å⁻³
2 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₅H₁₂Br₂N₂O₂	V = 3268.4 (10) Å³
M_r = 412.09	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.636 (3) Å	µ = 4.97 mm⁻¹
b = 9.606 (2) Å	T = 298 K
c = 19.943 (3) Å	0.17 × 0.13 × 0.12 mm
β = 113.726 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6973 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2208 reflections with I > 2σ(I)
T_min = 0.486, T_max = 0.587	R_int = 0.116
17117 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	2 restraints
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	Δρ_max = 0.32 e Å⁻³
6973 reflections	Δρ_min = −0.49 e Å⁻³
389 parameters

Special details top

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	0.69344 (6)	0.40876 (10)	0.38431 (6)	0.0971 (4)
Br2	0.72350 (5)	−0.17458 (10)	0.37439 (6)	0.0928 (4)
Br3	−0.06953 (6)	0.85420 (10)	−0.01006 (5)	0.0876 (4)
Br4	−0.12081 (6)	0.29585 (11)	0.04659 (6)	0.0984 (4)
N1	0.4069 (4)	0.1700 (7)	0.3119 (3)	0.0615 (18)
N2	0.3301 (4)	0.1455 (7)	0.3007 (4)	0.0614 (19)
N3	0.1898 (4)	0.6601 (6)	0.2214 (3)	0.0576 (18)
N4	0.2608 (4)	0.6440 (7)	0.2795 (4)	0.0605 (18)
O1	0.5235 (3)	0.3360 (6)	0.3345 (3)	0.0757 (17)
H1	0.4775	0.3154	0.3240	0.114*
O2	0.3146 (3)	0.3703 (6)	0.3204 (3)	0.0781 (18)
O3	0.0844 (3)	0.8048 (6)	0.1160 (3)	0.0726 (16)
H3	0.1266	0.7907	0.1504	0.109*
O4	0.2768 (3)	0.8762 (6)	0.2838 (3)	0.0822 (19)
C1	0.5314 (4)	0.0854 (9)	0.3282 (4)	0.051 (2)
C2	0.5659 (5)	0.2190 (9)	0.3415 (4)	0.057 (2)
C3	0.6469 (5)	0.2318 (8)	0.3630 (4)	0.060 (2)
C4	0.6930 (5)	0.1155 (10)	0.3713 (4)	0.067 (2)
H4A	0.7467	0.1249	0.3851	0.081*
C5	0.6590 (5)	−0.0157 (9)	0.3591 (4)	0.065 (2)
C6	0.5792 (5)	−0.0284 (9)	0.3376 (4)	0.058 (2)
H6	0.5569	−0.1168	0.3292	0.069*
C7	0.4486 (4)	0.0642 (9)	0.3118 (4)	0.057 (2)
H7	0.4265	−0.0242	0.3015	0.069*
C8	0.2854 (5)	0.2545 (10)	0.3053 (4)	0.055 (2)
C9	0.2028 (5)	0.2208 (9)	0.2904 (5)	0.061 (2)
C10	0.1668 (6)	0.2838 (11)	0.3318 (5)	0.088 (3)
C11	0.0869 (7)	0.2519 (13)	0.3119 (7)	0.109 (4)
H11	0.0607	0.2906	0.3384	0.131*
C12	0.0470 (7)	0.1646 (14)	0.2540 (7)	0.111 (4)
H12	−0.0059	0.1473	0.2417	0.133*
C13	0.0832 (6)	0.1029 (9)	0.2144 (6)	0.089 (3)
H13	0.0561	0.0433	0.1757	0.107*
C14	0.1627 (5)	0.1327 (9)	0.2342 (5)	0.073 (3)
H14	0.1888	0.0911	0.2083	0.087*
C15	0.0682 (4)	0.5631 (8)	0.1399 (4)	0.048 (2)
C16	0.0418 (5)	0.6869 (9)	0.1003 (4)	0.054 (2)
C17	−0.0330 (5)	0.6879 (9)	0.0439 (4)	0.059 (2)
C18	−0.0814 (5)	0.5726 (9)	0.0281 (4)	0.066 (2)
H18	−0.1315	0.5755	−0.0090	0.079*
C19	−0.0538 (4)	0.4536 (8)	0.0683 (4)	0.057 (2)
C20	0.0207 (4)	0.4455 (9)	0.1218 (4)	0.056 (2)
H20	0.0394	0.3616	0.1458	0.067*
C21	0.1458 (4)	0.5550 (8)	0.1993 (4)	0.051 (2)
H21	0.1636	0.4695	0.2217	0.061*
C22	0.3020 (5)	0.7621 (9)	0.3066 (4)	0.051 (2)
C23	0.3807 (5)	0.7368 (8)	0.3682 (4)	0.051 (2)
C24	0.4012 (5)	0.8118 (9)	0.4335 (5)	0.065 (2)
C25	0.4759 (7)	0.7929 (11)	0.4871 (5)	0.103 (3)
H25	0.4908	0.8405	0.5312	0.124*
C26	0.5285 (6)	0.7049 (11)	0.4762 (6)	0.102 (3)
H26	0.5786	0.6952	0.5129	0.122*
C27	0.5087 (5)	0.6310 (10)	0.4121 (6)	0.102 (3)
H27	0.5443	0.5710	0.4052	0.122*
C28	0.4339 (5)	0.6489 (9)	0.3583 (5)	0.075 (3)
H28	0.4193	0.6003	0.3145	0.090*
C29	0.2102 (6)	0.3762 (12)	0.3981 (6)	0.138 (5)
H29A	0.2560	0.3286	0.4313	0.208*
H29B	0.1763	0.3970	0.4226	0.208*
H29C	0.2254	0.4613	0.3822	0.208*
C30	0.3438 (6)	0.9038 (10)	0.4487 (5)	0.111 (4)
H30A	0.3303	0.9819	0.4159	0.167*
H30B	0.3673	0.9365	0.4983	0.167*
H30C	0.2974	0.8516	0.4415	0.167*
H4	0.281 (4)	0.559 (3)	0.295 (4)	0.080*
H2	0.309 (4)	0.060 (3)	0.291 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0765 (7)	0.0809 (7)	0.1295 (9)	−0.0250 (6)	0.0369 (7)	−0.0015 (7)
Br2	0.0685 (6)	0.0922 (8)	0.1017 (8)	0.0176 (6)	0.0175 (6)	−0.0253 (6)
Br3	0.0767 (7)	0.0865 (8)	0.0826 (7)	0.0029 (5)	0.0143 (6)	0.0252 (6)
Br4	0.0707 (7)	0.0878 (8)	0.1113 (8)	−0.0274 (6)	0.0101 (6)	−0.0070 (6)
N1	0.051 (5)	0.047 (4)	0.067 (5)	−0.004 (4)	0.004 (4)	0.006 (4)
N2	0.046 (5)	0.045 (5)	0.083 (5)	−0.004 (4)	0.015 (4)	0.007 (4)
N3	0.051 (4)	0.051 (4)	0.059 (5)	−0.013 (4)	0.009 (4)	−0.015 (4)
N4	0.040 (4)	0.056 (5)	0.065 (5)	0.005 (4)	0.000 (4)	0.001 (4)
O1	0.049 (3)	0.062 (4)	0.104 (5)	−0.003 (3)	0.019 (4)	0.015 (3)
O2	0.060 (4)	0.057 (4)	0.107 (5)	0.006 (3)	0.022 (4)	−0.006 (4)
O3	0.060 (4)	0.066 (4)	0.073 (4)	−0.019 (3)	0.006 (3)	0.006 (3)
O4	0.069 (4)	0.047 (4)	0.095 (5)	−0.004 (3)	−0.004 (4)	0.012 (4)
C1	0.050 (5)	0.054 (6)	0.041 (5)	−0.007 (5)	0.009 (4)	−0.006 (4)
C2	0.053 (6)	0.064 (7)	0.041 (5)	−0.002 (5)	0.005 (4)	0.005 (5)
C3	0.060 (6)	0.061 (6)	0.049 (5)	−0.013 (5)	0.010 (5)	−0.001 (4)
C4	0.053 (5)	0.091 (8)	0.055 (6)	0.006 (6)	0.018 (5)	−0.007 (6)
C5	0.062 (6)	0.073 (7)	0.056 (6)	0.010 (5)	0.019 (5)	−0.021 (5)
C6	0.050 (5)	0.063 (6)	0.050 (5)	−0.003 (5)	0.009 (4)	−0.010 (5)
C7	0.042 (5)	0.057 (6)	0.061 (5)	−0.006 (5)	0.009 (4)	0.001 (5)
C8	0.046 (6)	0.053 (6)	0.047 (5)	−0.010 (5)	0.000 (4)	0.006 (5)
C9	0.048 (6)	0.054 (6)	0.075 (7)	−0.011 (5)	0.019 (5)	0.001 (5)
C10	0.087 (8)	0.112 (9)	0.071 (7)	−0.003 (7)	0.038 (7)	0.017 (6)
C11	0.085 (9)	0.168 (12)	0.096 (9)	0.009 (8)	0.058 (8)	0.026 (9)
C12	0.074 (8)	0.164 (13)	0.101 (10)	−0.006 (8)	0.042 (8)	0.051 (9)
C13	0.073 (8)	0.080 (7)	0.105 (8)	−0.008 (6)	0.026 (7)	0.028 (6)
C14	0.048 (6)	0.066 (7)	0.101 (8)	0.005 (5)	0.027 (6)	0.017 (6)
C15	0.055 (5)	0.040 (5)	0.046 (5)	0.006 (4)	0.019 (4)	−0.001 (4)
C16	0.051 (5)	0.060 (6)	0.054 (6)	−0.010 (5)	0.024 (5)	−0.017 (5)
C17	0.046 (5)	0.074 (6)	0.049 (5)	0.009 (5)	0.011 (5)	0.018 (5)
C18	0.052 (5)	0.082 (7)	0.060 (6)	−0.019 (6)	0.018 (5)	−0.007 (5)
C19	0.050 (5)	0.050 (6)	0.057 (6)	−0.004 (4)	0.007 (5)	−0.002 (5)
C20	0.044 (5)	0.064 (6)	0.046 (5)	0.000 (5)	0.004 (4)	−0.010 (4)
C21	0.046 (5)	0.061 (6)	0.034 (5)	0.007 (4)	0.003 (4)	−0.009 (4)
C22	0.049 (5)	0.056 (6)	0.046 (5)	−0.018 (5)	0.016 (5)	−0.009 (5)
C23	0.052 (5)	0.049 (5)	0.049 (6)	−0.008 (4)	0.017 (5)	−0.005 (4)
C24	0.067 (6)	0.073 (6)	0.049 (6)	−0.002 (5)	0.017 (5)	−0.004 (5)
C25	0.104 (9)	0.116 (9)	0.055 (7)	0.005 (8)	−0.004 (7)	−0.018 (6)
C26	0.074 (8)	0.101 (9)	0.093 (9)	−0.013 (7)	−0.007 (7)	−0.013 (7)
C27	0.058 (7)	0.092 (8)	0.114 (9)	0.006 (6)	−0.008 (6)	−0.028 (7)
C28	0.058 (6)	0.078 (7)	0.070 (6)	−0.004 (5)	0.005 (6)	−0.003 (5)
C29	0.124 (10)	0.209 (14)	0.103 (9)	−0.013 (9)	0.067 (8)	−0.035 (9)
C30	0.121 (8)	0.144 (10)	0.078 (7)	0.008 (8)	0.049 (7)	−0.012 (7)

Geometric parameters (Å, º) top

Br1—C3	1.878 (8)	C11—H11	0.9300
Br2—C5	1.890 (8)	C12—C13	1.364 (13)
Br3—C17	1.894 (7)	C12—H12	0.9300
Br4—C19	1.900 (8)	C13—C14	1.402 (11)
N1—C7	1.280 (8)	C13—H13	0.9300
N1—N2	1.377 (8)	C14—H14	0.9300
N2—C8	1.364 (10)	C15—C20	1.391 (9)
N2—H2	0.898 (10)	C15—C16	1.402 (10)
N3—C21	1.263 (8)	C15—C21	1.457 (9)
N3—N4	1.372 (8)	C16—C17	1.396 (10)
N4—C22	1.355 (9)	C17—C18	1.382 (10)
N4—H4	0.898 (10)	C18—C19	1.371 (10)
O1—C2	1.348 (8)	C18—H18	0.9300
O1—H1	0.8200	C19—C20	1.370 (9)
O2—C8	1.221 (8)	C20—H20	0.9300
O3—C16	1.345 (8)	C21—H21	0.9300
O3—H3	0.8200	C22—C23	1.507 (10)
O4—C22	1.207 (8)	C23—C28	1.375 (10)
C1—C6	1.375 (9)	C23—C24	1.400 (10)
C1—C2	1.412 (10)	C24—C25	1.384 (11)
C1—C7	1.457 (9)	C24—C30	1.508 (11)
C2—C3	1.399 (10)	C25—C26	1.378 (12)
C3—C4	1.377 (10)	C25—H25	0.9300
C4—C5	1.387 (10)	C26—C27	1.376 (12)
C4—H4A	0.9300	C26—H26	0.9300
C5—C6	1.378 (9)	C27—C28	1.386 (11)
C6—H6	0.9300	C27—H27	0.9300
C7—H7	0.9300	C28—H28	0.9300
C8—C9	1.481 (10)	C29—H29A	0.9600
C9—C14	1.363 (10)	C29—H29B	0.9600
C9—C10	1.396 (11)	C29—H29C	0.9600
C10—C11	1.411 (13)	C30—H30A	0.9600
C10—C29	1.526 (12)	C30—H30B	0.9600
C11—C12	1.377 (14)	C30—H30C	0.9600

C7—N1—N2	117.1 (6)	C20—C15—C21	119.2 (7)
C8—N2—N1	118.7 (6)	C16—C15—C21	120.8 (7)
C8—N2—H2	119 (5)	O3—C16—C17	119.1 (8)
N1—N2—H2	122 (5)	O3—C16—C15	122.9 (7)
C21—N3—N4	118.3 (7)	C17—C16—C15	118.0 (8)
C22—N4—N3	116.2 (6)	C18—C17—C16	121.8 (8)
C22—N4—H4	122 (5)	C18—C17—Br3	119.6 (6)
N3—N4—H4	122 (5)	C16—C17—Br3	118.6 (7)
C2—O1—H1	109.5	C19—C18—C17	118.5 (7)
C16—O3—H3	109.5	C19—C18—H18	120.8
C6—C1—C2	118.4 (7)	C17—C18—H18	120.8
C6—C1—C7	119.3 (8)	C20—C19—C18	121.8 (7)
C2—C1—C7	122.1 (8)	C20—C19—Br4	119.9 (7)
O1—C2—C3	118.3 (8)	C18—C19—Br4	118.3 (6)
O1—C2—C1	122.3 (7)	C19—C20—C15	119.7 (7)
C3—C2—C1	119.4 (8)	C19—C20—H20	120.2
C4—C3—C2	120.6 (8)	C15—C20—H20	120.2
C4—C3—Br1	119.9 (7)	N3—C21—C15	122.2 (7)
C2—C3—Br1	119.5 (7)	N3—C21—H21	118.9
C3—C4—C5	119.8 (8)	C15—C21—H21	118.9
C3—C4—H4A	120.1	O4—C22—N4	122.5 (8)
C5—C4—H4A	120.1	O4—C22—C23	123.9 (7)
C6—C5—C4	119.6 (8)	N4—C22—C23	113.6 (8)
C6—C5—Br2	121.0 (7)	C28—C23—C24	120.5 (8)
C4—C5—Br2	119.3 (7)	C28—C23—C22	120.2 (7)
C1—C6—C5	122.1 (8)	C24—C23—C22	119.1 (8)
C1—C6—H6	119.0	C25—C24—C23	117.6 (9)
C5—C6—H6	119.0	C25—C24—C30	119.7 (9)
N1—C7—C1	118.5 (7)	C23—C24—C30	122.6 (8)
N1—C7—H7	120.8	C26—C25—C24	121.2 (9)
C1—C7—H7	120.8	C26—C25—H25	119.4
O2—C8—N2	119.5 (7)	C24—C25—H25	119.4
O2—C8—C9	124.9 (9)	C27—C26—C25	121.4 (10)
N2—C8—C9	115.6 (8)	C27—C26—H26	119.3
C14—C9—C10	121.4 (8)	C25—C26—H26	119.3
C14—C9—C8	118.9 (9)	C26—C27—C28	117.7 (9)
C10—C9—C8	119.7 (9)	C26—C27—H27	121.1
C9—C10—C11	116.3 (10)	C28—C27—H27	121.1
C9—C10—C29	123.5 (10)	C23—C28—C27	121.6 (9)
C11—C10—C29	120.1 (11)	C23—C28—H28	119.2
C12—C11—C10	121.4 (11)	C27—C28—H28	119.2
C12—C11—H11	119.3	C10—C29—H29A	109.5
C10—C11—H11	119.3	C10—C29—H29B	109.5
C13—C12—C11	121.6 (11)	H29A—C29—H29B	109.5
C13—C12—H12	119.2	C10—C29—H29C	109.5
C11—C12—H12	119.2	H29A—C29—H29C	109.5
C12—C13—C14	117.5 (10)	H29B—C29—H29C	109.5
C12—C13—H13	121.2	C24—C30—H30A	109.5
C14—C13—H13	121.2	C24—C30—H30B	109.5
C9—C14—C13	121.7 (9)	H30A—C30—H30B	109.5
C9—C14—H14	119.1	C24—C30—H30C	109.5
C13—C14—H14	119.1	H30A—C30—H30C	109.5
C20—C15—C16	120.0 (7)	H30B—C30—H30C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.90 (1)	1.85 (2)	2.743 (8)	172 (7)
N4—H4···O2	0.90 (1)	1.92 (2)	2.815 (8)	174 (7)
O3—H3···N3	0.82	1.90	2.624 (8)	146
O1—H1···N1	0.82	1.87	2.584 (8)	145

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂Br₂N₂O₂
M_r	412.09
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	18.636 (3), 9.606 (2), 19.943 (3)
β (°)	113.726 (2)
V (Å³)	3268.4 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.97
Crystal size (mm)	0.17 × 0.13 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.486, 0.587
No. of measured, independent and observed [I > 2σ(I)] reflections	17117, 6973, 2208
R_int	0.116
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.159, 0.89
No. of reflections	6973
No. of parameters	389
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.49

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.898 (10)	1.851 (17)	2.743 (8)	172 (7)
N4—H4···O2	0.898 (10)	1.921 (15)	2.815 (8)	174 (7)
O3—H3···N3	0.82	1.90	2.624 (8)	145.9
O1—H1···N1	0.82	1.87	2.584 (8)	145.4

Symmetry code: (i) x, y−1, z.

Acknowledgements

Financial support from the Jiaying University research fund is gratefully acknowledged.

References

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