4-Chloro-N′-(3,5-dibromo-2-hy­droxy­benzyl­idene)benzohydrazide

Zhang, W.-G.

doi:10.1107/S1600536812009786

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1209

doi:10.1107/S1600536812009786

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4-Chloro-N′-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide

Wei-Guang Zhang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, People's Republic of China
^*Correspondence e-mail: zhangweiguang1230@163.com

(Received 2 March 2012; accepted 5 March 2012; online 28 March 2012)

The asymmetric unit of the title compound, C₁₄H₉Br₂ClN₂O₂, contains two independent molecules. Both molecules adopt an E configuration about the C=N bond. The dihedral angles between the benzene rings are 30.0 (2) and 51.6 (2)° in the two molecules. In the crystal, molecules are linked through N—H⋯O hydrogen bonds, forming chains along the b axis. In addition, there is an intramolecular O—H⋯N hydrogen bond in each molecule.

Related literature

For the biological properties of hydrazone compounds, see: Ajani et al. (2010 ); Angelusiu et al. (2010 ); Zhang et al. (2010 ); Horiuchi et al. (2009 ). For the crystal structures of similar hydrazone compounds, see: Ban (2010 ); Hussain et al. (2010 ); Shalash et al. (2010 ); Khaledi et al. (2009 ). For related structures reported recently by the author, see: Zhang (2011 , 2012 ).

Experimental

Crystal data

C₁₄H₉Br₂ClN₂O₂
M_r = 432.50
Monoclinic, C 2/c
a = 21.0503 (19) Å
b = 9.9895 (11) Å
c = 30.185 (2) Å
β = 101.836 (2)°
V = 6212.4 (10) Å³
Z = 16
Mo Kα radiation
μ = 5.40 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.412, T_max = 0.461
21727 measured reflections
5775 independent reflections
2828 reflections with I > 2σ(I)
R_int = 0.093

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.105
S = 0.95
5775 reflections
389 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O2ⁱ	0.90 (1)	1.95 (2)	2.827 (5)	166 (4)
N2—H2⋯O4	0.90 (1)	2.08 (2)	2.941 (5)	160 (4)
O3—H3⋯N3	0.82	1.87	2.569 (5)	143
O1—H1⋯N1	0.82	1.87	2.590 (5)	146
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812009786/lh5429sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009786/lh5429Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009786/lh5429Isup3.cml

checkCIF report

Comment top

Benzoylhydrazones are a kind of special Schiff bases bearing the –C(O)—NH—N═CH– group. Hydrazone compounds have received much attention for their excellent biological properties (Ajani et al., 2010; Angelusiu et al., 2010; Zhang et al., 2010; Horiuchi et al., 2009) as well as their crystal structures (Ban, 2010; Hussain et al., 2010; Shalash et al., 2010; Khaledi et al., 2009). Recently, the author has reported some hydrazone compounds (Zhang, 2011; Zhang, 2012). In the present paper, the title new hydrazone compound, derived from the reaction of 3,5-dibromo-4-chlorobenzaldehyde with 4-chlorobenzohydrazide, is reported.

The asymmetric unit of the title hydrazone compound contains two independent molecules, as shown in Fig. 1. Each of the molecules of the compound adopts an E configuration about the C═N double bond. The dihedral angles between the two substituted benzene rings are 30.0 (2)° [C1-C6/C9-C14] and 51.6 (2)° [C15-C20/C23-C28]. In the crystal, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the b axis (Fig. 2). In addition, there is an intramolecular O—H···N hydrogen bond in each molecule.

Related literature top

For the biological properties of hydrazone compounds, see: Ajani et al. (2010); Angelusiu et al. (2010); Zhang et al. (2010); Horiuchi et al. (2009). For the crystal structures of similar hydrazone compounds, see: Ban (2010); Hussain et al. (2010); Shalash et al. (2010); Khaledi et al. (2009). For related structures reported recently by the author, see: Zhang (2011, 2012).

Experimental top

3,5-Dibromo-2-hydroxybenzaldehyde (0.280 g, 1 mmol) and 4-chlorobenzohydrazide (0.171 g, 1 mmol) were mixed in 50 ml methanol. The mixture was stirred and refluxed for 30 min and cooled to room temperature to give a colorless solution. Colorless block-shaped single crystals were obtained on slow evaporation of the solution in air.

Structure description top

For the biological properties of hydrazone compounds, see: Ajani et al. (2010); Angelusiu et al. (2010); Zhang et al. (2010); Horiuchi et al. (2009). For the crystal structures of similar hydrazone compounds, see: Ban (2010); Hussain et al. (2010); Shalash et al. (2010); Khaledi et al. (2009). For related structures reported recently by the author, see: Zhang (2011, 2012).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The molecular packing of the title compound viewed approximately along the a axis. Hydrogen bonds are shown as dashed lines. H-atoms not involved in hydrogen bonding have been omitted for clarity.

4-Chloro-N'-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide top

Crystal data top

C₁₄H₉Br₂ClN₂O₂	F(000) = 3360
M_r = 432.50	D_x = 1.850 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2652 reflections
a = 21.0503 (19) Å	θ = 2.3–24.3°
b = 9.9895 (11) Å	µ = 5.40 mm⁻¹
c = 30.185 (2) Å	T = 298 K
β = 101.836 (2)°	Block, colorless
V = 6212.4 (10) Å³	0.20 × 0.18 × 0.17 mm
Z = 16

Data collection top

Bruker APEXII CCD area-detector diffractometer	5775 independent reflections
Radiation source: fine-focus sealed tube	2828 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→25
T_min = 0.412, T_max = 0.461	k = −12→12
21727 measured reflections	l = −36→33

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0375P)²] where P = (F_o² + 2F_c²)/3
5775 reflections	(Δ/σ)_max = 0.001
389 parameters	Δρ_max = 0.53 e Å⁻³
2 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₄H₉Br₂ClN₂O₂	V = 6212.4 (10) Å³
M_r = 432.50	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 21.0503 (19) Å	µ = 5.40 mm⁻¹
b = 9.9895 (11) Å	T = 298 K
c = 30.185 (2) Å	0.20 × 0.18 × 0.17 mm
β = 101.836 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5775 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2828 reflections with I > 2σ(I)
T_min = 0.412, T_max = 0.461	R_int = 0.093
21727 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	2 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.53 e Å⁻³
5775 reflections	Δρ_min = −0.59 e Å⁻³
389 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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

	x	y	z	U_iso*/U_eq
Br1	0.59984 (4)	−0.15649 (7)	0.50684 (2)	0.0893 (3)
Br2	0.60096 (5)	0.40530 (8)	0.51878 (3)	0.1266 (4)
Br3	0.16100 (3)	0.32156 (6)	0.13346 (2)	0.0621 (2)
Br4	0.13920 (3)	0.88180 (6)	0.11656 (2)	0.0662 (2)
Cl1	0.28553 (8)	0.0539 (2)	0.08490 (5)	0.0867 (6)
Cl2	0.69898 (8)	0.5736 (2)	0.42951 (6)	0.0988 (7)
N1	0.48103 (18)	0.0501 (4)	0.34395 (14)	0.0364 (10)
N2	0.4503 (2)	0.0679 (4)	0.29989 (14)	0.0393 (11)
N3	0.3518 (2)	0.5527 (4)	0.25814 (14)	0.0429 (11)
N4	0.4089 (2)	0.5744 (4)	0.28790 (15)	0.0452 (12)
O1	0.5259 (2)	−0.0988 (3)	0.41356 (11)	0.0564 (11)
H1	0.5103	−0.0831	0.3869	0.085*
O2	0.44485 (17)	−0.1529 (3)	0.28785 (12)	0.0522 (10)
O3	0.26677 (17)	0.3947 (3)	0.21220 (12)	0.0469 (9)
H3	0.3028	0.4132	0.2271	0.070*
O4	0.43685 (17)	0.3578 (3)	0.28369 (11)	0.0496 (10)
C1	0.5296 (2)	0.1408 (5)	0.41481 (18)	0.0409 (14)
C2	0.5433 (2)	0.0165 (5)	0.43546 (18)	0.0444 (14)
C3	0.5777 (3)	0.0117 (6)	0.48000 (19)	0.0544 (16)
C4	0.5949 (3)	0.1262 (6)	0.50448 (19)	0.0688 (19)
H4A	0.6173	0.1215	0.5344	0.083*
C5	0.5787 (3)	0.2482 (6)	0.4843 (2)	0.0661 (19)
C6	0.5472 (3)	0.2557 (5)	0.44034 (19)	0.0547 (16)
H6	0.5373	0.3392	0.4271	0.066*
C7	0.4980 (2)	0.1532 (5)	0.36838 (18)	0.0430 (14)
H7	0.4896	0.2380	0.3558	0.052*
C8	0.4314 (2)	−0.0407 (5)	0.27356 (18)	0.0385 (13)
C9	0.3945 (2)	−0.0126 (5)	0.22721 (17)	0.0355 (13)
C10	0.3549 (2)	0.0978 (5)	0.21643 (18)	0.0464 (15)
H10	0.3515	0.1596	0.2389	0.056*
C11	0.3200 (3)	0.1184 (6)	0.1727 (2)	0.0550 (16)
H11	0.2930	0.1924	0.1657	0.066*
C12	0.3265 (3)	0.0269 (6)	0.13990 (18)	0.0499 (15)
C13	0.3631 (3)	−0.0858 (6)	0.1497 (2)	0.0564 (16)
H13	0.3650	−0.1487	0.1273	0.068*
C14	0.3976 (2)	−0.1056 (5)	0.19342 (19)	0.0460 (14)
H14	0.4231	−0.1818	0.2003	0.055*
C15	0.2601 (2)	0.6341 (5)	0.20665 (17)	0.0387 (13)
C16	0.2386 (2)	0.5064 (5)	0.19194 (17)	0.0373 (13)
C17	0.1875 (2)	0.4942 (5)	0.15544 (17)	0.0393 (13)
C18	0.1587 (2)	0.6050 (6)	0.13239 (17)	0.0460 (14)
H18	0.1263	0.5948	0.1066	0.055*
C19	0.1784 (3)	0.7297 (5)	0.14789 (17)	0.0421 (14)
C20	0.2292 (2)	0.7460 (5)	0.18405 (16)	0.0412 (14)
H20	0.2431	0.8316	0.1935	0.049*
C21	0.3177 (2)	0.6530 (5)	0.24191 (16)	0.0417 (14)
H21	0.3297	0.7386	0.2526	0.050*
C22	0.4500 (2)	0.4694 (5)	0.29903 (17)	0.0400 (14)
C23	0.5113 (3)	0.5008 (5)	0.33136 (16)	0.0351 (13)
C24	0.5150 (3)	0.5908 (5)	0.36667 (17)	0.0451 (15)
H24	0.4781	0.6385	0.3696	0.054*
C25	0.5719 (3)	0.6111 (5)	0.39751 (19)	0.0507 (15)
H25	0.5731	0.6693	0.4217	0.061*
C26	0.6262 (3)	0.5457 (6)	0.3924 (2)	0.0537 (16)
C27	0.6246 (3)	0.4561 (6)	0.3576 (2)	0.0648 (18)
H27	0.6620	0.4107	0.3545	0.078*
C28	0.5668 (3)	0.4343 (5)	0.32730 (18)	0.0510 (15)
H28	0.5656	0.3736	0.3038	0.061*
H2	0.440 (2)	0.150 (2)	0.2886 (14)	0.039 (15)*
H4	0.4239 (18)	0.6586 (17)	0.2928 (13)	0.028 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1524 (8)	0.0620 (5)	0.0432 (4)	0.0235 (5)	−0.0042 (4)	0.0114 (4)
Br2	0.2209 (11)	0.0680 (5)	0.0661 (6)	−0.0248 (6)	−0.0282 (6)	−0.0228 (4)
Br3	0.0642 (4)	0.0549 (4)	0.0575 (4)	−0.0059 (3)	−0.0101 (3)	−0.0099 (3)
Br4	0.0726 (5)	0.0615 (4)	0.0599 (4)	0.0200 (3)	0.0025 (3)	0.0202 (4)
Cl1	0.0802 (12)	0.1304 (16)	0.0417 (10)	−0.0018 (12)	−0.0056 (9)	0.0045 (10)
Cl2	0.0554 (11)	0.1279 (17)	0.0980 (15)	−0.0097 (11)	−0.0196 (10)	−0.0172 (13)
N1	0.043 (3)	0.033 (3)	0.029 (3)	−0.004 (2)	−0.002 (2)	0.005 (2)
N2	0.054 (3)	0.025 (3)	0.035 (3)	0.003 (2)	0.000 (2)	0.000 (2)
N3	0.051 (3)	0.032 (3)	0.040 (3)	0.001 (2)	−0.004 (2)	0.005 (2)
N4	0.048 (3)	0.026 (3)	0.050 (3)	−0.004 (2)	−0.016 (2)	0.003 (2)
O1	0.093 (3)	0.035 (2)	0.035 (2)	0.003 (2)	−0.001 (2)	0.0007 (18)
O2	0.065 (3)	0.028 (2)	0.058 (3)	−0.0016 (19)	−0.002 (2)	0.0050 (19)
O3	0.054 (3)	0.034 (2)	0.046 (3)	−0.0019 (18)	−0.0069 (19)	−0.0033 (18)
O4	0.072 (3)	0.024 (2)	0.045 (2)	−0.0014 (18)	−0.009 (2)	−0.0068 (17)
C1	0.047 (3)	0.032 (3)	0.042 (4)	0.002 (3)	0.007 (3)	0.001 (3)
C2	0.052 (4)	0.033 (3)	0.047 (4)	0.003 (3)	0.006 (3)	0.000 (3)
C3	0.074 (4)	0.050 (4)	0.036 (4)	0.004 (3)	0.002 (3)	0.009 (3)
C4	0.097 (5)	0.069 (5)	0.030 (4)	−0.006 (4)	−0.010 (3)	−0.010 (4)
C5	0.099 (5)	0.051 (4)	0.038 (4)	−0.007 (4)	−0.011 (4)	−0.007 (3)
C6	0.079 (5)	0.038 (4)	0.045 (4)	−0.004 (3)	0.006 (3)	0.003 (3)
C7	0.054 (4)	0.033 (3)	0.040 (4)	−0.008 (3)	0.003 (3)	0.005 (3)
C8	0.040 (3)	0.023 (3)	0.050 (4)	−0.001 (3)	0.005 (3)	−0.001 (3)
C9	0.029 (3)	0.032 (3)	0.046 (4)	−0.003 (3)	0.007 (3)	−0.002 (3)
C10	0.053 (4)	0.041 (3)	0.042 (4)	0.007 (3)	0.000 (3)	−0.006 (3)
C11	0.057 (4)	0.049 (4)	0.054 (4)	0.006 (3)	0.000 (3)	0.001 (3)
C12	0.044 (4)	0.069 (4)	0.035 (4)	−0.011 (3)	0.003 (3)	0.001 (3)
C13	0.058 (4)	0.059 (4)	0.048 (4)	−0.007 (3)	0.004 (3)	−0.016 (3)
C14	0.044 (4)	0.038 (3)	0.052 (4)	0.005 (3)	0.001 (3)	−0.012 (3)
C15	0.043 (3)	0.039 (3)	0.035 (3)	0.003 (3)	0.009 (3)	0.003 (3)
C16	0.043 (3)	0.030 (3)	0.037 (3)	0.004 (3)	0.004 (3)	0.001 (3)
C17	0.037 (3)	0.046 (3)	0.034 (3)	0.003 (3)	0.004 (3)	−0.005 (3)
C18	0.045 (4)	0.062 (4)	0.028 (3)	0.008 (3)	0.001 (3)	0.004 (3)
C19	0.051 (4)	0.044 (4)	0.029 (3)	0.010 (3)	0.003 (3)	0.010 (3)
C20	0.049 (4)	0.033 (3)	0.041 (4)	0.005 (3)	0.009 (3)	0.009 (3)
C21	0.055 (4)	0.033 (3)	0.035 (3)	−0.008 (3)	0.003 (3)	0.003 (3)
C22	0.049 (4)	0.034 (3)	0.033 (3)	−0.002 (3)	0.000 (3)	0.006 (3)
C23	0.047 (4)	0.027 (3)	0.029 (3)	0.002 (3)	0.003 (3)	0.006 (2)
C24	0.052 (4)	0.031 (3)	0.045 (4)	0.010 (3)	−0.009 (3)	−0.006 (3)
C25	0.057 (4)	0.037 (3)	0.053 (4)	−0.007 (3)	0.000 (3)	−0.005 (3)
C26	0.042 (4)	0.056 (4)	0.058 (4)	−0.005 (3)	−0.001 (3)	0.005 (3)
C27	0.055 (4)	0.071 (5)	0.071 (5)	0.015 (4)	0.020 (4)	0.003 (4)
C28	0.058 (4)	0.054 (4)	0.042 (4)	−0.001 (3)	0.010 (3)	−0.003 (3)

Geometric parameters (Å, º) top

Br1—C3	1.882 (5)	C9—C10	1.380 (6)
Br2—C5	1.888 (6)	C9—C14	1.391 (6)
Br3—C17	1.890 (5)	C10—C11	1.389 (7)
Br4—C19	1.888 (5)	C10—H10	0.9300
Cl1—C12	1.727 (5)	C11—C12	1.374 (7)
Cl2—C26	1.724 (6)	C11—H11	0.9300
N1—C7	1.274 (5)	C12—C13	1.363 (7)
N1—N2	1.366 (5)	C13—C14	1.383 (7)
N2—C8	1.356 (6)	C13—H13	0.9300
N2—H2	0.897 (10)	C14—H14	0.9300
N3—C21	1.271 (5)	C15—C16	1.396 (6)
N3—N4	1.362 (5)	C15—C20	1.398 (6)
N4—C22	1.357 (6)	C15—C21	1.452 (7)
N4—H4	0.900 (10)	C16—C17	1.379 (6)
O1—C2	1.341 (5)	C17—C18	1.379 (6)
O1—H1	0.8200	C18—C19	1.364 (7)
O2—C8	1.213 (5)	C18—H18	0.9300
O3—C16	1.349 (5)	C19—C20	1.373 (7)
O3—H3	0.8200	C20—H20	0.9300
O4—C22	1.217 (5)	C21—H21	0.9300
C1—C6	1.390 (6)	C22—C23	1.484 (6)
C1—C2	1.393 (6)	C23—C28	1.371 (7)
C1—C7	1.428 (7)	C23—C24	1.384 (6)
C2—C3	1.390 (7)	C24—C25	1.374 (7)
C3—C4	1.370 (7)	C24—H24	0.9300
C4—C5	1.374 (7)	C25—C26	1.352 (7)
C4—H4A	0.9300	C25—H25	0.9300
C5—C6	1.357 (7)	C26—C27	1.376 (7)
C6—H6	0.9300	C27—C28	1.380 (7)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.482 (6)	C28—H28	0.9300

C7—N1—N2	118.6 (4)	C12—C13—H13	120.4
C8—N2—N1	119.3 (4)	C14—C13—H13	120.4
C8—N2—H2	119 (3)	C13—C14—C9	120.6 (5)
N1—N2—H2	121 (3)	C13—C14—H14	119.7
C21—N3—N4	118.8 (4)	C9—C14—H14	119.7
C22—N4—N3	118.2 (4)	C16—C15—C20	119.2 (5)
C22—N4—H4	120 (3)	C16—C15—C21	121.3 (5)
N3—N4—H4	119 (3)	C20—C15—C21	119.3 (5)
C2—O1—H1	109.5	O3—C16—C17	119.2 (5)
C16—O3—H3	109.5	O3—C16—C15	121.9 (4)
C6—C1—C2	118.7 (5)	C17—C16—C15	119.0 (5)
C6—C1—C7	119.3 (5)	C18—C17—C16	121.5 (5)
C2—C1—C7	121.9 (5)	C18—C17—Br3	119.2 (4)
O1—C2—C3	118.8 (5)	C16—C17—Br3	119.1 (4)
O1—C2—C1	122.3 (5)	C19—C18—C17	119.3 (5)
C3—C2—C1	118.9 (5)	C19—C18—H18	120.4
C4—C3—C2	121.3 (5)	C17—C18—H18	120.4
C4—C3—Br1	119.9 (4)	C18—C19—C20	120.9 (5)
C2—C3—Br1	118.8 (4)	C18—C19—Br4	119.5 (4)
C3—C4—C5	119.1 (5)	C20—C19—Br4	119.5 (4)
C3—C4—H4A	120.4	C19—C20—C15	120.1 (5)
C5—C4—H4A	120.4	C19—C20—H20	119.9
C6—C5—C4	120.6 (5)	C15—C20—H20	119.9
C6—C5—Br2	120.6 (5)	N3—C21—C15	120.1 (5)
C4—C5—Br2	118.8 (4)	N3—C21—H21	120.0
C5—C6—C1	121.2 (5)	C15—C21—H21	120.0
C5—C6—H6	119.4	O4—C22—N4	122.0 (5)
C1—C6—H6	119.4	O4—C22—C23	122.9 (5)
N1—C7—C1	121.1 (5)	N4—C22—C23	115.1 (5)
N1—C7—H7	119.5	C28—C23—C24	118.0 (5)
C1—C7—H7	119.5	C28—C23—C22	118.8 (5)
O2—C8—N2	120.8 (5)	C24—C23—C22	123.2 (5)
O2—C8—C9	123.4 (5)	C25—C24—C23	121.3 (5)
N2—C8—C9	115.8 (4)	C25—C24—H24	119.3
C10—C9—C14	118.6 (5)	C23—C24—H24	119.3
C10—C9—C8	123.3 (5)	C26—C25—C24	119.5 (5)
C14—C9—C8	118.1 (5)	C26—C25—H25	120.2
C9—C10—C11	121.2 (5)	C24—C25—H25	120.2
C9—C10—H10	119.4	C25—C26—C27	120.8 (5)
C11—C10—H10	119.4	C25—C26—Cl2	120.5 (5)
C12—C11—C10	118.4 (5)	C27—C26—Cl2	118.8 (5)
C12—C11—H11	120.8	C26—C27—C28	119.3 (6)
C10—C11—H11	120.8	C26—C27—H27	120.3
C13—C12—C11	121.9 (5)	C28—C27—H27	120.3
C13—C12—Cl1	119.1 (5)	C23—C28—C27	121.0 (5)
C11—C12—Cl1	119.0 (5)	C23—C28—H28	119.5
C12—C13—C14	119.3 (5)	C27—C28—H28	119.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2ⁱ	0.90 (1)	1.95 (2)	2.827 (5)	166 (4)
N2—H2···O4	0.90 (1)	2.08 (2)	2.941 (5)	160 (4)
O3—H3···N3	0.82	1.87	2.569 (5)	143
O1—H1···N1	0.82	1.87	2.590 (5)	146

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₉Br₂ClN₂O₂
M_r	432.50
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	21.0503 (19), 9.9895 (11), 30.185 (2)
β (°)	101.836 (2)
V (Å³)	6212.4 (10)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	5.40
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.412, 0.461
No. of measured, independent and observed [I > 2σ(I)] reflections	21727, 5775, 2828
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.105, 0.95
No. of reflections	5775
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)	0.53, −0.59

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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
N4—H4···O2ⁱ	0.900 (10)	1.947 (15)	2.827 (5)	166 (4)
N2—H2···O4	0.897 (10)	2.081 (18)	2.941 (5)	160 (4)
O3—H3···N3	0.82	1.87	2.569 (5)	142.9
O1—H1···N1	0.82	1.87	2.590 (5)	145.6

Symmetry code: (i) x, y+1, z.

Acknowledgements

Financial support from Qiqihar University is acknowledged.

References

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