N′-(3,5-Dibromo-2-hydroxy­benzyl­idene)-3,4-methyl­enedioxy­benzohydrazide

Sang, Y.-L.; Lin, X.-S.

doi:10.1107/S160053680902282X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1631-o1632

doi:10.1107/S160053680902282X

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N′-(3,5-Dibromo-2-hydroxybenzylidene)-3,4-methylenedioxybenzohydrazide

Ya-Li Sang ^a ^* and Xue-Song Lin ^a

^aDepartment of Chemistry, Chifeng University, Chifeng 024001, People's Republic of China
^*Correspondence e-mail: sangyali0814@126.com

(Received 8 June 2009; accepted 13 June 2009; online 20 June 2009)

In the asymmetric unit of the title hydrazone compound, C₁₅H₁₀Br₂N₂O₄, there are two independent molecules. In each molecule, the five-membered ring adopts a flattened envelope conformation; the flap atoms are displaced by 0.114 (2) and 0.219 (2) Å from the planes of the other four atoms. In one molecule the dihedral angle between the two benzene rings is 22.8 (2)°, while in the other it is 40.8 (2)°. Each molecule displays an E configuration with respect to the C=N bond. In both molecules, intramolecular O—H⋯N hydrogen bonds are observed. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological properties of hydrazones, see: Khattab et al. (2005 ); Küçükgüzel et al. (2003 ); Cukurovali et al. (2006 ). For their coordination chemistry, see: Iskander et al. (2001 ); Bernhardt et al. (2004 ); Aggarwal et al. (1981 ); Thomas et al. (1979 ). For the crystal structures of other reported hydrazones, see: Fun et al. (2008 ); Wei et al. (2009 ); Khaledi et al. (2008 ); Yang et al. (2008 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₀Br₂N₂O₄
M_r = 442.07
Triclinic, $[P \overline 1]$
a = 9.793 (1) Å
b = 13.188 (2) Å
c = 13.342 (2) Å
α = 76.282 (2)°
β = 78.350 (2)°
γ = 75.911 (2)°
V = 1604.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 5.07 mm⁻¹
T = 298 K
0.23 × 0.21 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.388, T_max = 0.416 (expected range = 0.322–0.345)
9190 measured reflections
6633 independent reflections
4090 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.141
S = 0.98
6633 reflections
423 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.55 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
O1—H1⋯N1	0.82	2.00	2.654 (4)	137
O5—H5⋯N3	0.82	1.86	2.582 (4)	146
N2—H2⋯O6ⁱ	0.91 (4)	1.99 (3)	2.833 (5)	155 (6)
N4—H4A⋯O2ⁱⁱ	0.90 (3)	2.04 (3)	2.888 (5)	158 (6)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

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: 10.1107/S160053680902282X/wn2332sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902282X/wn2332Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds have been widely investigated due to their interesting biological properties, such as antibacterial and antitumor activities (Khattab et al., 2005; Küçükgüzel et al., 2003; Cukurovali et al., 2006). Furthermore, hydrazones are excellent ligands in coordination chemistry, forming a large number of metal complexes (Iskander et al., 2001; Bernhardt et al., 2004; Aggarwal et al., 1981; Thomas et al., 1979). Recently, the crystal structures of a large number of hydrazone derivatives have been reported (Fun et al., 2008; Wei et al., 2009; Khaledi et al., 2008; Yang et al., 2008). In this paper, the crystal structure of the new title hydrazone compound is reported.

In the asymmetric unit there are two independent molecules (Fig. 1), which assume E configurations with respect to the C═N bonds. In each molecule the five-membered ring adopts a flattened envelope conformation; the flap atoms C15 and C30 are displaced by 0.114 (2) and 0.219 (2) Å, respectively, from the planes of the other four atoms. In one molecule the dihedral angle between the two benzene rings is 22.8 (2)°; in the other it is 40.8 (2)°. All bond lengths are within normal values (Allen et al., 1987). In both molecules, intramolecular O—H···N hydrogen bonds (Table 1) are observed. In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the a axis, as shown in Fig. 2.

Related literature top

For the biological properties of hydrazones, see: Khattab et al. (2005); Küçükgüzel et al. (2003); Cukurovali et al. (2006). For their coordination chemistry, see: Iskander et al. (2001); Bernhardt et al. (2004); Aggarwal et al. (1981); Thomas et al. (1979). For the crystal structures of other reported hydrazones, see: Fun et al. (2008); Wei et al. (2009); Khaledi et al. (2008); Yang et al. (2008). For reference structural data, see: Allen et al. (1987).

Experimental top

3,4-(Methylenedioxy)benzohydrazide (1.0 mmol, 180.2 mg) and 3,5-dibromo-2-hydroxybenzaldehyde (1.0 mmol, 280.0 mg) were mixed and refluxed in aqueous ethanol (95% ethanol : 5% water; 50 ml). The mixture was stirred for 1 h to give a clear colorless solution. Colorless crystals of the title compound were formed by slow evaporation of the solution in air.

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 asymmetric unit, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius. The intramolecular O—H···N hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

N'-(3,5-Dibromo-2-hydroxybenzylidene)-3,4-methylenedioxybenzohydrazide top

Crystal data top

C₁₅H₁₀Br₂N₂O₄	Z = 4
M_r = 442.07	F(000) = 864
Triclinic, P1	D_x = 1.830 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.793 (1) Å	Cell parameters from 2697 reflections
b = 13.188 (2) Å	θ = 2.8–25.0°
c = 13.342 (2) Å	µ = 5.07 mm⁻¹
α = 76.282 (2)°	T = 298 K
β = 78.350 (2)°	Block, colorless
γ = 75.911 (2)°	0.23 × 0.21 × 0.21 mm
V = 1604.5 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	6633 independent reflections
Radiation source: fine-focus sealed tube	4090 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.0°, θ_min = 4.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.388, T_max = 0.416	k = −16→15
9190 measured reflections	l = −17→11

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0781P)²] where P = (F_o² + 2F_c²)/3
6633 reflections	(Δ/σ)_max < 0.001
423 parameters	Δρ_max = 1.55 e Å⁻³
2 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₁₅H₁₀Br₂N₂O₄	γ = 75.911 (2)°
M_r = 442.07	V = 1604.5 (4) Å³
Triclinic, P1	Z = 4
a = 9.793 (1) Å	Mo Kα radiation
b = 13.188 (2) Å	µ = 5.07 mm⁻¹
c = 13.342 (2) Å	T = 298 K
α = 76.282 (2)°	0.23 × 0.21 × 0.21 mm
β = 78.350 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6633 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4090 reflections with I > 2σ(I)
T_min = 0.388, T_max = 0.416	R_int = 0.026
9190 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	2 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 1.55 e Å⁻³
6633 reflections	Δρ_min = −0.66 e Å⁻³
423 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	0.88068 (7)	−0.00513 (5)	0.23288 (6)	0.0870 (3)
Br2	0.34278 (8)	0.02682 (5)	0.11846 (5)	0.0719 (2)
Br3	−0.32989 (6)	0.72142 (5)	1.11784 (4)	0.0662 (2)
Br4	0.22028 (8)	0.81059 (6)	1.05222 (5)	0.0793 (2)
O1	0.7359 (3)	0.2022 (3)	0.2943 (3)	0.0472 (8)
H1	0.6914	0.2499	0.3252	0.071*
O2	0.6613 (3)	0.4996 (2)	0.3674 (3)	0.0436 (8)
O3	0.2556 (4)	0.9420 (3)	0.4051 (3)	0.0590 (10)
O4	0.4456 (4)	0.8602 (3)	0.4941 (3)	0.0544 (9)
O5	−0.2006 (3)	0.6068 (3)	0.9410 (3)	0.0479 (8)
H5	−0.1640	0.5740	0.8939	0.072*
O6	−0.1740 (3)	0.4855 (3)	0.7024 (3)	0.0524 (9)
O7	0.1423 (4)	0.1701 (3)	0.4070 (3)	0.0612 (10)
O8	−0.0796 (3)	0.2781 (3)	0.3989 (2)	0.0488 (8)
N1	0.5281 (4)	0.3734 (3)	0.3031 (3)	0.0369 (8)
N2	0.4637 (4)	0.4735 (3)	0.3238 (3)	0.0380 (9)
N3	−0.0003 (4)	0.5372 (3)	0.8002 (3)	0.0347 (8)
N4	0.0506 (4)	0.4792 (3)	0.7230 (3)	0.0350 (8)
C1	0.5062 (5)	0.2213 (3)	0.2451 (3)	0.0380 (10)
C2	0.6449 (5)	0.1653 (3)	0.2556 (3)	0.0379 (10)
C3	0.6891 (6)	0.0677 (4)	0.2253 (4)	0.0510 (13)
C4	0.6019 (6)	0.0259 (4)	0.1848 (4)	0.0532 (13)
H4	0.6347	−0.0397	0.1644	0.064*
C5	0.4658 (6)	0.0817 (4)	0.1746 (4)	0.0469 (12)
C6	0.4184 (5)	0.1777 (4)	0.2045 (4)	0.0426 (11)
H6	0.3258	0.2147	0.1977	0.051*
C7	0.4504 (5)	0.3269 (4)	0.2715 (4)	0.0406 (11)
H7	0.3564	0.3604	0.2651	0.049*
C8	0.5382 (4)	0.5336 (3)	0.3505 (3)	0.0317 (9)
C9	0.4569 (4)	0.6426 (3)	0.3609 (3)	0.0317 (9)
C10	0.3485 (5)	0.6950 (3)	0.3049 (3)	0.0384 (10)
H10	0.3239	0.6611	0.2595	0.046*
C11	0.2739 (5)	0.7982 (4)	0.3140 (4)	0.0419 (11)
H11	0.2002	0.8332	0.2761	0.050*
C12	0.3136 (5)	0.8447 (3)	0.3803 (4)	0.0396 (10)
C13	0.4260 (5)	0.7940 (3)	0.4349 (3)	0.0358 (10)
C14	0.4984 (5)	0.6931 (4)	0.4290 (3)	0.0366 (10)
H14	0.5715	0.6590	0.4678	0.044*
C15	0.3443 (6)	0.9581 (4)	0.4691 (4)	0.0577 (14)
H15A	0.2874	0.9781	0.5326	0.069*
H15B	0.3936	1.0149	0.4326	0.069*
C16	0.0381 (5)	0.6371 (3)	0.9138 (3)	0.0367 (10)
C17	−0.1030 (5)	0.6495 (3)	0.9648 (3)	0.0366 (10)
C18	−0.1420 (5)	0.7085 (4)	1.0440 (3)	0.0440 (11)
C19	−0.0483 (6)	0.7567 (4)	1.0706 (3)	0.0521 (13)
H19	−0.0774	0.7972	1.1224	0.062*
C20	0.0896 (6)	0.7436 (4)	1.0186 (4)	0.0506 (12)
C21	0.1344 (5)	0.6834 (4)	0.9426 (3)	0.0424 (11)
H21	0.2289	0.6734	0.9103	0.051*
C22	0.0877 (5)	0.5754 (3)	0.8309 (3)	0.0364 (10)
H22	0.1831	0.5642	0.8007	0.044*
C23	−0.0460 (4)	0.4517 (3)	0.6800 (3)	0.0336 (9)
C24	0.0118 (4)	0.3775 (3)	0.6071 (3)	0.0317 (9)
C25	0.1441 (5)	0.3100 (4)	0.6128 (4)	0.0473 (12)
H25	0.1990	0.3145	0.6603	0.057*
C26	0.1955 (5)	0.2359 (4)	0.5486 (5)	0.0587 (15)
H26	0.2835	0.1896	0.5527	0.070*
C27	0.1127 (5)	0.2339 (4)	0.4800 (4)	0.0415 (11)
C28	−0.0185 (4)	0.2998 (3)	0.4727 (3)	0.0334 (9)
C29	−0.0732 (4)	0.3735 (3)	0.5354 (3)	0.0342 (9)
H29	−0.1619	0.4185	0.5307	0.041*
C30	0.0117 (6)	0.1849 (4)	0.3679 (4)	0.0559 (14)
H30A	0.0291	0.1941	0.2924	0.067*
H30B	−0.0318	0.1234	0.3967	0.067*
H2	0.377 (3)	0.505 (5)	0.305 (5)	0.080*
H4A	0.1436 (19)	0.467 (5)	0.697 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0757 (4)	0.0627 (4)	0.1261 (6)	0.0277 (3)	−0.0345 (4)	−0.0524 (4)
Br2	0.1068 (5)	0.0619 (4)	0.0702 (4)	−0.0450 (3)	−0.0267 (3)	−0.0179 (3)
Br3	0.0642 (4)	0.0676 (4)	0.0628 (4)	−0.0100 (3)	0.0140 (3)	−0.0288 (3)
Br4	0.1044 (5)	0.0985 (5)	0.0648 (4)	−0.0527 (4)	−0.0215 (3)	−0.0338 (3)
O1	0.0423 (18)	0.040 (2)	0.066 (2)	0.0011 (15)	−0.0170 (16)	−0.0261 (16)
O2	0.0331 (17)	0.0389 (18)	0.064 (2)	−0.0039 (14)	−0.0126 (15)	−0.0191 (15)
O3	0.065 (2)	0.0368 (19)	0.082 (3)	0.0148 (17)	−0.0351 (19)	−0.0318 (18)
O4	0.063 (2)	0.045 (2)	0.065 (2)	0.0106 (17)	−0.0285 (18)	−0.0352 (17)
O5	0.0418 (17)	0.053 (2)	0.056 (2)	−0.0102 (16)	−0.0053 (15)	−0.0247 (16)
O6	0.0313 (17)	0.062 (2)	0.076 (2)	−0.0016 (15)	−0.0097 (15)	−0.0445 (19)
O7	0.052 (2)	0.059 (2)	0.088 (3)	0.0105 (17)	−0.0254 (19)	−0.053 (2)
O8	0.0481 (18)	0.051 (2)	0.056 (2)	0.0064 (15)	−0.0226 (16)	−0.0316 (16)
N1	0.040 (2)	0.0268 (19)	0.045 (2)	−0.0009 (16)	−0.0092 (16)	−0.0143 (16)
N2	0.0318 (19)	0.0283 (19)	0.059 (2)	0.0029 (15)	−0.0149 (17)	−0.0211 (17)
N3	0.0373 (19)	0.036 (2)	0.0343 (19)	−0.0067 (16)	−0.0067 (15)	−0.0141 (16)
N4	0.0303 (18)	0.038 (2)	0.042 (2)	−0.0048 (16)	−0.0051 (16)	−0.0200 (16)
C1	0.043 (3)	0.031 (2)	0.045 (3)	−0.004 (2)	−0.011 (2)	−0.0160 (19)
C2	0.047 (3)	0.030 (2)	0.039 (2)	−0.006 (2)	−0.008 (2)	−0.0133 (19)
C3	0.060 (3)	0.035 (3)	0.055 (3)	0.005 (2)	−0.012 (2)	−0.014 (2)
C4	0.077 (4)	0.032 (3)	0.055 (3)	−0.006 (3)	−0.012 (3)	−0.020 (2)
C5	0.069 (3)	0.038 (3)	0.043 (3)	−0.026 (3)	−0.012 (2)	−0.008 (2)
C6	0.047 (3)	0.037 (3)	0.047 (3)	−0.014 (2)	−0.006 (2)	−0.009 (2)
C7	0.037 (2)	0.034 (2)	0.055 (3)	−0.003 (2)	−0.012 (2)	−0.017 (2)
C8	0.028 (2)	0.032 (2)	0.037 (2)	−0.0064 (18)	−0.0020 (17)	−0.0125 (18)
C9	0.031 (2)	0.031 (2)	0.035 (2)	−0.0070 (18)	−0.0026 (17)	−0.0096 (18)
C10	0.042 (2)	0.031 (2)	0.048 (3)	−0.0060 (19)	−0.016 (2)	−0.012 (2)
C11	0.046 (3)	0.031 (2)	0.051 (3)	0.002 (2)	−0.024 (2)	−0.011 (2)
C12	0.046 (3)	0.026 (2)	0.045 (3)	0.0014 (19)	−0.008 (2)	−0.0113 (19)
C13	0.040 (2)	0.035 (2)	0.036 (2)	−0.0028 (19)	−0.0084 (19)	−0.0186 (19)
C14	0.036 (2)	0.037 (2)	0.039 (2)	−0.0025 (19)	−0.0119 (18)	−0.0128 (19)
C15	0.067 (3)	0.045 (3)	0.066 (3)	0.009 (3)	−0.023 (3)	−0.033 (3)
C16	0.047 (3)	0.032 (2)	0.035 (2)	−0.006 (2)	−0.0144 (19)	−0.0099 (18)
C17	0.041 (2)	0.031 (2)	0.038 (2)	−0.0076 (19)	−0.0064 (19)	−0.0072 (19)
C18	0.054 (3)	0.035 (3)	0.040 (3)	−0.005 (2)	−0.005 (2)	−0.006 (2)
C19	0.076 (4)	0.050 (3)	0.033 (3)	−0.013 (3)	−0.005 (2)	−0.016 (2)
C20	0.071 (3)	0.054 (3)	0.039 (3)	−0.024 (3)	−0.016 (2)	−0.015 (2)
C21	0.047 (3)	0.049 (3)	0.038 (2)	−0.017 (2)	−0.008 (2)	−0.013 (2)
C22	0.035 (2)	0.039 (3)	0.037 (2)	−0.0048 (19)	−0.0068 (18)	−0.012 (2)
C23	0.030 (2)	0.035 (2)	0.039 (2)	−0.0068 (18)	−0.0081 (18)	−0.0116 (19)
C24	0.029 (2)	0.024 (2)	0.044 (2)	−0.0033 (17)	−0.0066 (18)	−0.0111 (18)
C25	0.042 (3)	0.047 (3)	0.064 (3)	−0.003 (2)	−0.024 (2)	−0.025 (2)
C26	0.041 (3)	0.050 (3)	0.097 (4)	0.015 (2)	−0.028 (3)	−0.048 (3)
C27	0.035 (2)	0.034 (2)	0.063 (3)	−0.0030 (19)	−0.010 (2)	−0.027 (2)
C28	0.036 (2)	0.031 (2)	0.035 (2)	−0.0048 (18)	−0.0124 (18)	−0.0071 (18)
C29	0.030 (2)	0.033 (2)	0.042 (2)	−0.0013 (18)	−0.0088 (18)	−0.0134 (19)
C30	0.058 (3)	0.051 (3)	0.068 (3)	0.004 (3)	−0.021 (3)	−0.037 (3)

Geometric parameters (Å, º) top

Br1—C3	1.899 (5)	C7—H7	0.9300
Br2—C5	1.893 (5)	C8—C9	1.488 (6)
Br3—C18	1.892 (5)	C9—C10	1.372 (6)
Br4—C20	1.895 (5)	C9—C14	1.415 (6)
O1—C2	1.347 (5)	C10—C11	1.399 (6)
O1—H1	0.8200	C10—H10	0.9300
O2—C8	1.226 (5)	C11—C12	1.348 (6)
O3—C12	1.361 (5)	C11—H11	0.9300
O3—C15	1.415 (6)	C12—C13	1.387 (6)
O4—C13	1.377 (5)	C13—C14	1.358 (6)
O4—C15	1.437 (6)	C14—H14	0.9300
O5—C17	1.343 (5)	C15—H15A	0.9700
O5—H5	0.8200	C15—H15B	0.9700
O6—C23	1.225 (5)	C16—C21	1.396 (6)
O7—C27	1.377 (5)	C16—C17	1.400 (6)
O7—C30	1.430 (6)	C16—C22	1.463 (6)
O8—C28	1.366 (5)	C17—C18	1.396 (6)
O8—C30	1.428 (5)	C18—C19	1.377 (7)
N1—C7	1.269 (6)	C19—C20	1.378 (7)
N1—N2	1.384 (5)	C19—H19	0.9300
N2—C8	1.345 (5)	C20—C21	1.372 (6)
N2—H2	0.91 (4)	C21—H21	0.9300
N3—C22	1.271 (5)	C22—H22	0.9300
N3—N4	1.370 (5)	C23—C24	1.477 (5)
N4—C23	1.357 (5)	C24—C25	1.386 (6)
N4—H4A	0.90 (3)	C24—C29	1.406 (6)
C1—C6	1.393 (6)	C25—C26	1.388 (6)
C1—C2	1.396 (6)	C25—H25	0.9300
C1—C7	1.465 (6)	C26—C27	1.348 (6)
C2—C3	1.384 (6)	C26—H26	0.9300
C3—C4	1.371 (7)	C27—C28	1.373 (6)
C4—C5	1.373 (7)	C28—C29	1.371 (6)
C4—H4	0.9300	C29—H29	0.9300
C5—C6	1.362 (6)	C30—H30A	0.9700
C6—H6	0.9300	C30—H30B	0.9700

C2—O1—H1	109.5	C9—C14—H14	121.7
C12—O3—C15	106.3 (3)	O3—C15—O4	108.3 (4)
C13—O4—C15	105.3 (3)	O3—C15—H15A	110.0
C17—O5—H5	109.5	O4—C15—H15A	110.0
C27—O7—C30	105.6 (3)	O3—C15—H15B	110.0
C28—O8—C30	105.7 (3)	O4—C15—H15B	110.0
C7—N1—N2	115.5 (3)	H15A—C15—H15B	108.4
C8—N2—N1	120.9 (3)	C21—C16—C17	119.9 (4)
C8—N2—H2	118 (4)	C21—C16—C22	118.8 (4)
N1—N2—H2	120 (4)	C17—C16—C22	121.3 (4)
C22—N3—N4	117.8 (3)	O5—C17—C18	119.3 (4)
C23—N4—N3	117.6 (3)	O5—C17—C16	122.7 (4)
C23—N4—H4A	121 (4)	C18—C17—C16	118.0 (4)
N3—N4—H4A	121 (4)	C19—C18—C17	122.3 (4)
C6—C1—C2	119.3 (4)	C19—C18—Br3	119.0 (4)
C6—C1—C7	118.2 (4)	C17—C18—Br3	118.7 (4)
C2—C1—C7	122.4 (4)	C18—C19—C20	118.4 (4)
O1—C2—C3	119.3 (4)	C18—C19—H19	120.8
O1—C2—C1	122.7 (4)	C20—C19—H19	120.8
C3—C2—C1	118.0 (4)	C21—C20—C19	121.5 (5)
C4—C3—C2	122.1 (4)	C21—C20—Br4	119.1 (4)
C4—C3—Br1	119.7 (4)	C19—C20—Br4	119.3 (4)
C2—C3—Br1	118.0 (4)	C20—C21—C16	119.9 (4)
C3—C4—C5	119.4 (4)	C20—C21—H21	120.1
C3—C4—H4	120.3	C16—C21—H21	120.1
C5—C4—H4	120.3	N3—C22—C16	119.6 (4)
C6—C5—C4	120.1 (5)	N3—C22—H22	120.2
C6—C5—Br2	119.4 (4)	C16—C22—H22	120.2
C4—C5—Br2	120.5 (4)	O6—C23—N4	121.2 (4)
C5—C6—C1	121.1 (4)	O6—C23—C24	122.4 (4)
C5—C6—H6	119.4	N4—C23—C24	116.4 (3)
C1—C6—H6	119.4	C25—C24—C29	120.9 (4)
N1—C7—C1	121.1 (4)	C25—C24—C23	120.5 (4)
N1—C7—H7	119.5	C29—C24—C23	118.5 (3)
C1—C7—H7	119.5	C24—C25—C26	120.8 (4)
O2—C8—N2	122.4 (4)	C24—C25—H25	119.6
O2—C8—C9	123.4 (4)	C26—C25—H25	119.6
N2—C8—C9	114.2 (3)	C27—C26—C25	117.3 (4)
C10—C9—C14	120.3 (4)	C27—C26—H26	121.4
C10—C9—C8	122.2 (4)	C25—C26—H26	121.4
C14—C9—C8	117.5 (4)	C26—C27—C28	123.0 (4)
C9—C10—C11	121.8 (4)	C26—C27—O7	127.8 (4)
C9—C10—H10	119.1	C28—C27—O7	109.1 (4)
C11—C10—H10	119.1	O8—C28—C29	128.4 (4)
C12—C11—C10	117.1 (4)	O8—C28—C27	110.3 (4)
C12—C11—H11	121.4	C29—C28—C27	121.3 (4)
C10—C11—H11	121.4	C28—C29—C24	116.6 (4)
C11—C12—O3	128.3 (4)	C28—C29—H29	121.7
C11—C12—C13	121.7 (4)	C24—C29—H29	121.7
O3—C12—C13	110.0 (4)	O8—C30—O7	107.0 (3)
C14—C13—O4	128.2 (4)	O8—C30—H30A	110.3
C14—C13—C12	122.4 (4)	O7—C30—H30A	110.3
O4—C13—C12	109.4 (4)	O8—C30—H30B	110.3
C13—C14—C9	116.6 (4)	O7—C30—H30B	110.3
C13—C14—H14	121.7	H30A—C30—H30B	108.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	2.00	2.654 (4)	137
O5—H5···N3	0.82	1.86	2.582 (4)	146
N2—H2···O6ⁱ	0.91 (4)	1.99 (3)	2.833 (5)	155 (6)
N4—H4A···O2ⁱⁱ	0.90 (3)	2.04 (3)	2.888 (5)	158 (6)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀Br₂N₂O₄
M_r	442.07
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.793 (1), 13.188 (2), 13.342 (2)
α, β, γ (°)	76.282 (2), 78.350 (2), 75.911 (2)
V (Å³)	1604.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.07
Crystal size (mm)	0.23 × 0.21 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.388, 0.416
No. of measured, independent and observed [I > 2σ(I)] reflections	9190, 6633, 4090
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.141, 0.98
No. of reflections	6633
No. of parameters	423
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)	1.55, −0.66

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
O1—H1···N1	0.82	2.00	2.654 (4)	137
O5—H5···N3	0.82	1.86	2.582 (4)	146
N2—H2···O6ⁱ	0.91 (4)	1.99 (3)	2.833 (5)	155 (6)
N4—H4A···O2ⁱⁱ	0.90 (3)	2.04 (3)	2.888 (5)	158 (6)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.

Acknowledgements

We are very grateful to Chifeng University for research funding.

References

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