(E)-Methyl 3-(3,5-dibromo-2-hy­droxy­benzyl­idene)carbazate

Lv, L.-P.; Liu, S.

doi:10.1107/S1600536810033799

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2405

https://doi.org/10.1107/S1600536810033799

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(E)-Methyl 3-(3,5-dibromo-2-hydroxybenzylidene)carbazate

Lu-Ping Lv ^a ^* and Songhui Liu ^a

^aLinjiang College, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China
^*Correspondence e-mail: mailofllp@126.com

(Received 21 August 2010; accepted 21 August 2010; online 28 August 2010)

The title compound, C₉H₈Br₂N₂O₃, crystallizes with two very similar independent molecules in the asymmetric unit, each of which adopts a trans configuration with respect to the C=N bond. Intramolecular O—H⋯N hydrogen bonds are observed in each independent molecule. In the crystal structure, molecules are linked into chains propagating along [010] by N—H⋯O and C—H⋯O hydrogen bonds. In addition, C—H⋯π interactions stabilize the structure.

Related literature

For general background to benzaldehydehydrazone derivatives, see: Parashar et al. (1988 ); Hadjoudis et al. (1987 ); Borg et al. (1999 ); Kahwa et al. (1986 ); Santos et al. (2001 ). For a related structure, see: Shang et al. (2007 ).

Experimental

Crystal data

C₉H₈Br₂N₂O₃
M_r = 351.99
Triclinic, $[P \overline 1]$
a = 7.6907 (11) Å
b = 9.9886 (14) Å
c = 15.503 (2) Å
α = 92.254 (6)°
β = 95.647 (6)°
γ = 91.394 (6)°
V = 1183.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 6.84 mm⁻¹
T = 223 K
0.22 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.977, T_max = 0.989
12305 measured reflections
4109 independent reflections
2425 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.175
S = 1.01
4109 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.604 (7)	146
N2—H2⋯O6	0.86	2.01	2.845 (6)	163
N4—H4⋯O2ⁱ	0.86	2.00	2.828 (6)	161
O4—H4A⋯N3	0.82	1.89	2.609 (7)	145
C7—H7⋯O6	0.93	2.56	3.312 (8)	139
C16—H16⋯O2ⁱ	0.93	2.52	3.282 (8)	139
C9—H9B⋯Cg1ⁱⁱ	0.97	2.89	3.594 (8)	131
C18—H18C⋯Cg2ⁱⁱⁱ	0.97	2.89	3.561 (8)	128
Symmetry codes: (i) x, y-1, z; (ii) -x, -y+2, -z+1; (iii) -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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810033799/ci5169sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033799/ci5169Isup2.hkl

checkCIF report

Comment top

Benzaldehydehydrazone derivatives have attracted much attention due to their pharmacological activity (Parashar et al., 1988) and their photochromic properties (Hadjoudis et al., 1987). They are important intermediates of 1,3,4-oxadiazoles, which have been reported to be versatile compounds with many interesting properties (Borg et al., 1999). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). We report here the crystal structure of the title compound (Fig. 1).

The title compound contains two independent, but almost identical molecules in the asymmetric unit. Each independent molecule adopts a trans configuration with respect to the C═N bond. The N1/N2/O2/O3/C7-C9 and N3/N4/O5/O6/C16-C18 planes form dihedral angles of 8.18 (6)° and 7.28 (7)°, respectively, with the C1—C6 and C10—C15 planes. The bond lengths and angles are comparable to those observed for methylN'-[(E)-4-methoxybenzylidene]hydrazinecarboxylate (Shang et al., 2007). Intramolecular O—H···N hydrogen bonds are observed in each independent molecule.

In the crystal structure, the molecules are linked into chains running along the [010] by N—H···O and C—H···O hydrogen bonds. In addition, intermolecular C—H···π interactions are observed, which further stabilize the structure (Table 1).

Related literature top

For general background to benzaldehydehydrazone derivatives, see: Parashar et al. (1988); Hadjoudis et al. (1987); Borg et al. (1999); Kahwa et al. (1986); Santos et al. (2001). For a related structure, see: Shang et al. (2007).

Experimental top

3,5-Dibromo-2-hydroxybenzaldehyde (2.79 g, 0.01 mol) and methyl hydrazinecarboxylate (0.90 g, 0.01 mol) were dissolved in stirred methanol (15 ml) and left for 5.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 96% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ispropanol solution at room temperature (m.p. 415–417 K).

Structure description top

For general background to benzaldehydehydrazone derivatives, see: Parashar et al. (1988); Hadjoudis et al. (1987); Borg et al. (1999); Kahwa et al. (1986); Santos et al. (2001). For a related structure, see: Shang et al. (2007).

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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 2. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

(E)-Methyl 3-(3,5-dibromo-2-hydroxybenzylidene)carbazate top

Crystal data top

C₉H₈Br₂N₂O₃	Z = 4
M_r = 351.99	F(000) = 680
Triclinic, P1	D_x = 1.975 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6907 (11) Å	Cell parameters from 4109 reflections
b = 9.9886 (14) Å	θ = 1.3–25.0°
c = 15.503 (2) Å	µ = 6.84 mm⁻¹
α = 92.254 (6)°	T = 223 K
β = 95.647 (6)°	Block, colourless
γ = 91.394 (6)°	0.22 × 0.21 × 0.18 mm
V = 1183.8 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4109 independent reflections
Radiation source: fine-focus sealed tube	2425 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
φ and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→8
T_min = 0.977, T_max = 0.989	k = −11→11
12305 measured reflections	l = −18→18

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0947P)²] where P = (F_o² + 2F_c²)/3
4109 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

C₉H₈Br₂N₂O₃	γ = 91.394 (6)°
M_r = 351.99	V = 1183.8 (3) Å³
Triclinic, P1	Z = 4
a = 7.6907 (11) Å	Mo Kα radiation
b = 9.9886 (14) Å	µ = 6.84 mm⁻¹
c = 15.503 (2) Å	T = 223 K
α = 92.254 (6)°	0.22 × 0.21 × 0.18 mm
β = 95.647 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4109 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2425 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.989	R_int = 0.059
12305 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.01	Δρ_max = 0.63 e Å⁻³
4109 reflections	Δρ_min = −0.62 e Å⁻³
289 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
C1	0.0209 (8)	0.9946 (6)	0.2567 (4)	0.0463 (16)
C2	−0.0373 (9)	1.0058 (7)	0.1701 (5)	0.0551 (18)
C3	−0.0724 (9)	0.8941 (7)	0.1156 (5)	0.0578 (19)
H3	−0.1108	0.9037	0.0568	0.069*
C4	−0.0513 (9)	0.7688 (7)	0.1474 (5)	0.0568 (19)
C5	0.0050 (8)	0.7525 (7)	0.2340 (5)	0.0529 (18)
H5	0.0167	0.6661	0.2554	0.063*
C6	0.0441 (8)	0.8656 (6)	0.2893 (4)	0.0428 (15)
C7	0.1087 (8)	0.8455 (6)	0.3787 (4)	0.0485 (16)
H7	0.1129	0.7586	0.3999	0.058*
C8	0.2901 (8)	1.0311 (6)	0.5634 (4)	0.0454 (16)
C9	0.4215 (10)	1.0965 (7)	0.7025 (5)	0.064 (2)
H9A	0.4648	1.0566	0.7562	0.096*
H9B	0.3295	1.1578	0.7135	0.096*
H9C	0.5162	1.1451	0.6795	0.096*
C10	0.3833 (8)	0.4911 (6)	0.2572 (4)	0.0436 (15)
C11	0.4111 (8)	0.4998 (7)	0.1704 (5)	0.0522 (17)
C12	0.4301 (8)	0.3882 (7)	0.1186 (5)	0.0582 (19)
H12	0.4482	0.3955	0.0599	0.070*
C13	0.4218 (9)	0.2622 (7)	0.1556 (5)	0.0528 (18)
C14	0.3968 (8)	0.2485 (6)	0.2395 (4)	0.0495 (17)
H14	0.3928	0.1627	0.2623	0.059*
C15	0.3769 (8)	0.3617 (6)	0.2927 (4)	0.0436 (15)
C16	0.3449 (8)	0.3454 (6)	0.3820 (4)	0.0465 (16)
H16	0.3494	0.2596	0.4048	0.056*
C17	0.2301 (8)	0.5304 (6)	0.5620 (4)	0.0427 (15)
C18	0.1545 (10)	0.5951 (7)	0.7015 (5)	0.063 (2)
H18A	0.1356	0.5552	0.7559	0.094*
H18B	0.0492	0.6388	0.6790	0.094*
H18C	0.2503	0.6607	0.7110	0.094*
N1	0.1604 (7)	0.9473 (5)	0.4288 (4)	0.0483 (14)
N2	0.2264 (7)	0.9247 (5)	0.5120 (4)	0.0542 (15)
H2	0.2274	0.8442	0.5313	0.065*
N3	0.3108 (7)	0.4455 (5)	0.4302 (3)	0.0452 (13)
N4	0.2761 (7)	0.4238 (5)	0.5131 (4)	0.0508 (14)
H4	0.2832	0.3443	0.5340	0.061*
O1	0.0559 (6)	1.1076 (4)	0.3070 (3)	0.0547 (12)
H1	0.0934	1.0875	0.3567	0.082*
O2	0.2888 (7)	1.1459 (4)	0.5407 (3)	0.0688 (15)
O3	0.3523 (6)	0.9915 (4)	0.6398 (3)	0.0557 (12)
O4	0.3642 (6)	0.6050 (4)	0.3056 (3)	0.0547 (12)
H4A	0.3491	0.5857	0.3559	0.082*
O5	0.1974 (6)	0.4908 (4)	0.6391 (3)	0.0569 (12)
O6	0.2219 (7)	0.6444 (4)	0.5383 (3)	0.0630 (14)
Br1	−0.06212 (11)	1.17836 (8)	0.12394 (5)	0.0693 (3)
Br2	−0.09610 (12)	0.61188 (8)	0.07391 (6)	0.0806 (3)
Br3	0.41876 (12)	0.67238 (8)	0.12264 (6)	0.0735 (3)
Br4	0.43692 (12)	0.10563 (8)	0.08150 (6)	0.0764 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.043 (4)	0.051 (4)	0.046 (5)	−0.004 (3)	0.010 (3)	−0.005 (3)
C2	0.053 (4)	0.060 (4)	0.054 (5)	0.003 (3)	0.009 (4)	0.007 (4)
C3	0.062 (4)	0.076 (5)	0.035 (4)	0.004 (4)	0.010 (3)	−0.001 (4)
C4	0.063 (4)	0.057 (4)	0.047 (5)	−0.007 (3)	0.000 (4)	−0.014 (4)
C5	0.053 (4)	0.053 (4)	0.052 (5)	0.007 (3)	0.009 (3)	−0.009 (3)
C6	0.052 (4)	0.042 (4)	0.035 (4)	0.000 (3)	0.013 (3)	−0.003 (3)
C7	0.061 (4)	0.039 (3)	0.047 (5)	0.004 (3)	0.011 (3)	−0.002 (3)
C8	0.061 (4)	0.042 (4)	0.034 (4)	0.003 (3)	0.012 (3)	0.000 (3)
C9	0.076 (5)	0.076 (5)	0.038 (5)	0.003 (4)	0.000 (4)	−0.008 (4)
C10	0.040 (3)	0.051 (4)	0.040 (4)	0.005 (3)	0.007 (3)	−0.002 (3)
C11	0.050 (4)	0.061 (4)	0.049 (5)	0.003 (3)	0.013 (3)	0.011 (4)
C12	0.053 (4)	0.078 (5)	0.043 (5)	0.001 (4)	0.006 (3)	−0.002 (4)
C13	0.054 (4)	0.063 (5)	0.040 (5)	0.004 (3)	0.008 (3)	−0.018 (3)
C14	0.061 (4)	0.049 (4)	0.039 (4)	−0.001 (3)	0.010 (3)	−0.008 (3)
C15	0.046 (4)	0.047 (4)	0.038 (4)	0.003 (3)	0.005 (3)	0.002 (3)
C16	0.053 (4)	0.039 (3)	0.048 (5)	0.001 (3)	0.008 (3)	0.003 (3)
C17	0.058 (4)	0.036 (4)	0.034 (4)	0.000 (3)	0.004 (3)	0.002 (3)
C18	0.079 (5)	0.070 (5)	0.040 (5)	0.000 (4)	0.015 (4)	−0.009 (4)
N1	0.067 (4)	0.042 (3)	0.036 (4)	0.002 (3)	0.002 (3)	0.003 (3)
N2	0.083 (4)	0.028 (3)	0.050 (4)	0.002 (3)	0.001 (3)	0.006 (3)
N3	0.066 (4)	0.037 (3)	0.034 (3)	0.003 (2)	0.013 (3)	0.001 (2)
N4	0.083 (4)	0.029 (3)	0.041 (4)	0.003 (3)	0.010 (3)	0.003 (3)
O1	0.079 (3)	0.048 (3)	0.037 (3)	−0.005 (2)	0.004 (2)	0.004 (2)
O2	0.114 (4)	0.025 (2)	0.067 (4)	−0.003 (2)	0.004 (3)	0.013 (2)
O3	0.091 (3)	0.041 (2)	0.032 (3)	−0.003 (2)	−0.005 (2)	0.005 (2)
O4	0.078 (3)	0.047 (3)	0.041 (3)	0.008 (2)	0.014 (2)	0.004 (2)
O5	0.087 (3)	0.049 (3)	0.037 (3)	0.008 (2)	0.016 (2)	0.002 (2)
O6	0.110 (4)	0.030 (2)	0.053 (3)	0.010 (2)	0.021 (3)	0.011 (2)
Br1	0.0837 (6)	0.0719 (5)	0.0532 (6)	0.0081 (4)	0.0047 (4)	0.0159 (4)
Br2	0.0933 (7)	0.0793 (6)	0.0647 (6)	0.0018 (5)	−0.0013 (5)	−0.0291 (5)
Br3	0.0975 (7)	0.0730 (6)	0.0543 (6)	0.0022 (4)	0.0234 (5)	0.0158 (4)
Br4	0.0873 (6)	0.0814 (6)	0.0595 (6)	0.0082 (4)	0.0131 (4)	−0.0301 (4)

Geometric parameters (Å, º) top

C1—O1	1.353 (7)	C11—C12	1.367 (9)
C1—C2	1.383 (9)	C11—Br3	1.905 (7)
C1—C6	1.412 (8)	C12—C13	1.406 (10)
C2—C3	1.378 (9)	C12—H12	0.94
C2—Br1	1.899 (7)	C13—C14	1.346 (9)
C3—C4	1.370 (9)	C13—Br4	1.917 (6)
C3—H3	0.94	C14—C15	1.393 (8)
C4—C5	1.387 (10)	C14—H14	0.94
C4—Br2	1.906 (7)	C15—C16	1.445 (9)
C5—C6	1.400 (8)	C16—N3	1.272 (7)
C5—H5	0.94	C16—H16	0.94
C6—C7	1.448 (9)	C17—O6	1.211 (7)
C7—N1	1.286 (7)	C17—O5	1.319 (7)
C7—H7	0.94	C17—N4	1.357 (7)
C8—O2	1.212 (7)	C18—O5	1.460 (7)
C8—O3	1.312 (8)	C18—H18A	0.97
C8—N2	1.355 (8)	C18—H18B	0.97
C9—O3	1.456 (7)	C18—H18C	0.97
C9—H9A	0.97	N1—N2	1.368 (7)
C9—H9B	0.97	N2—H2	0.87
C9—H9C	0.97	N3—N4	1.364 (7)
C10—O4	1.357 (7)	N4—H4	0.87
C10—C11	1.388 (9)	O1—H1	0.83
C10—C15	1.426 (8)	O4—H4A	0.83

O1—C1—C2	118.9 (6)	C11—C12—C13	118.1 (7)
O1—C1—C6	122.2 (6)	C11—C12—H12	120.9
C2—C1—C6	118.9 (6)	C13—C12—H12	120.9
C3—C2—C1	121.3 (7)	C14—C13—C12	122.3 (6)
C3—C2—Br1	119.1 (6)	C14—C13—Br4	119.6 (6)
C1—C2—Br1	119.6 (5)	C12—C13—Br4	118.0 (5)
C4—C3—C2	119.8 (7)	C13—C14—C15	119.8 (6)
C4—C3—H3	120.1	C13—C14—H14	120.1
C2—C3—H3	120.1	C15—C14—H14	120.1
C3—C4—C5	121.0 (6)	C14—C15—C10	119.4 (6)
C3—C4—Br2	121.1 (6)	C14—C15—C16	119.3 (6)
C5—C4—Br2	117.9 (5)	C10—C15—C16	121.3 (6)
C4—C5—C6	119.5 (6)	N3—C16—C15	120.9 (6)
C4—C5—H5	120.3	N3—C16—H16	119.5
C6—C5—H5	120.3	C15—C16—H16	119.5
C5—C6—C1	119.5 (6)	O6—C17—O5	125.5 (6)
C5—C6—C7	118.3 (6)	O6—C17—N4	125.0 (6)
C1—C6—C7	122.2 (6)	O5—C17—N4	109.5 (5)
N1—C7—C6	119.5 (6)	O5—C18—H18A	109.5
N1—C7—H7	120.2	O5—C18—H18B	109.5
C6—C7—H7	120.2	H18A—C18—H18B	109.5
O2—C8—O3	125.8 (6)	O5—C18—H18C	109.5
O2—C8—N2	123.9 (6)	H18A—C18—H18C	109.5
O3—C8—N2	110.4 (5)	H18B—C18—H18C	109.5
O3—C9—H9A	109.5	C7—N1—N2	118.2 (5)
O3—C9—H9B	109.5	C8—N2—N1	118.3 (5)
H9A—C9—H9B	109.5	C8—N2—H2	120.9
O3—C9—H9C	109.5	N1—N2—H2	120.9
H9A—C9—H9C	109.5	C16—N3—N4	118.5 (5)
H9B—C9—H9C	109.5	C17—N4—N3	117.7 (5)
O4—C10—C11	119.4 (6)	C17—N4—H4	121.2
O4—C10—C15	122.1 (6)	N3—N4—H4	121.2
C11—C10—C15	118.5 (6)	C1—O1—H1	109.5
C12—C11—C10	121.8 (6)	C8—O3—C9	116.1 (5)
C12—C11—Br3	119.5 (6)	C10—O4—H4A	109.5
C10—C11—Br3	118.6 (5)	C17—O5—C18	116.5 (5)

O1—C1—C2—C3	179.0 (6)	C11—C12—C13—C14	−0.3 (11)
C6—C1—C2—C3	−0.1 (10)	C11—C12—C13—Br4	177.0 (5)
O1—C1—C2—Br1	1.2 (8)	C12—C13—C14—C15	0.5 (10)
C6—C1—C2—Br1	−177.9 (4)	Br4—C13—C14—C15	−176.8 (5)
C1—C2—C3—C4	0.6 (11)	C13—C14—C15—C10	0.0 (10)
Br1—C2—C3—C4	178.5 (5)	C13—C14—C15—C16	178.2 (6)
C2—C3—C4—C5	0.1 (11)	O4—C10—C15—C14	179.8 (5)
C2—C3—C4—Br2	−179.3 (5)	C11—C10—C15—C14	−0.6 (9)
C3—C4—C5—C6	−1.3 (10)	O4—C10—C15—C16	1.7 (9)
Br2—C4—C5—C6	178.1 (5)	C11—C10—C15—C16	−178.7 (6)
C4—C5—C6—C1	1.8 (9)	C14—C15—C16—N3	−173.7 (6)
C4—C5—C6—C7	−177.7 (6)	C10—C15—C16—N3	4.4 (9)
O1—C1—C6—C5	179.8 (6)	C6—C7—N1—N2	−177.8 (5)
C2—C1—C6—C5	−1.1 (9)	O2—C8—N2—N1	1.6 (10)
O1—C1—C6—C7	−0.7 (9)	O3—C8—N2—N1	−178.3 (5)
C2—C1—C6—C7	178.4 (6)	C7—N1—N2—C8	176.3 (6)
C5—C6—C7—N1	173.9 (6)	C15—C16—N3—N4	177.9 (5)
C1—C6—C7—N1	−5.7 (9)	O6—C17—N4—N3	−2.1 (10)
O4—C10—C11—C12	−179.6 (6)	O5—C17—N4—N3	178.5 (5)
C15—C10—C11—C12	0.8 (10)	C16—N3—N4—C17	−176.3 (6)
O4—C10—C11—Br3	−0.7 (8)	O2—C8—O3—C9	1.5 (10)
C15—C10—C11—Br3	179.7 (4)	N2—C8—O3—C9	−178.6 (6)
C10—C11—C12—C13	−0.4 (10)	O6—C17—O5—C18	−2.5 (10)
Br3—C11—C12—C13	−179.3 (5)	N4—C17—O5—C18	176.9 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.604 (7)	146
N2—H2···O6	0.86	2.01	2.845 (6)	163
N4—H4···O2ⁱ	0.86	2.00	2.828 (6)	161
O4—H4A···N3	0.82	1.89	2.609 (7)	145
C7—H7···O6	0.93	2.56	3.312 (8)	139
C16—H16···O2ⁱ	0.93	2.52	3.282 (8)	139
C9—H9B···Cg1ⁱⁱ	0.97	2.89	3.594 (8)	131
C18—H18C···Cg2ⁱⁱⁱ	0.97	2.89	3.561 (8)	128

Symmetry codes: (i) x, y−1, z; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₉H₈Br₂N₂O₃
M_r	351.99
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	7.6907 (11), 9.9886 (14), 15.503 (2)
α, β, γ (°)	92.254 (6), 95.647 (6), 91.394 (6)
V (Å³)	1183.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.84
Crystal size (mm)	0.22 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.977, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	12305, 4109, 2425
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.175, 1.01
No. of reflections	4109
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.62

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.604 (7)	146
N2—H2···O6	0.86	2.01	2.845 (6)	163
N4—H4···O2ⁱ	0.86	2.00	2.828 (6)	161
O4—H4A···N3	0.82	1.89	2.609 (7)	145
C7—H7···O6	0.93	2.56	3.312 (8)	139
C16—H16···O2ⁱ	0.93	2.52	3.282 (8)	139
C9—H9B···Cg1ⁱⁱ	0.97	2.89	3.594 (8)	131
C18—H18C···Cg2ⁱⁱⁱ	0.97	2.89	3.561 (8)	128

Symmetry codes: (i) x, y−1, z; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank Hangzhou Vocational and Technical College for financial support.

References

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