N′-(3,5-Dibromo-2-hy­droxy­benzyl­idene)-4-nitro­benzohydrazide methanol monosolvate

Zhou, X.; Gao, S.-T.; Ma, J.-J.

doi:10.1107/S1600536811031187

organic compounds

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Volume 67| Part 9| September 2011| Page o2275

doi:10.1107/S1600536811031187

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N′-(3,5-Dibromo-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol monosolvate

Xin Zhou,^a Shu-Tao Gao ^a and Jing-Jun Ma ^a ^*

^aHebei Key Laboratory of Bioinorganic Chemistry, College of Sciences, Agricultural University of Hebei, Baoding 071001, People's Republic of China
^*Correspondence e-mail: majingjun71@yahoo.cn

(Received 23 July 2011; accepted 2 August 2011; online 11 August 2011)

The title compound, C₁₄H₉Br₂N₃O₄·CH₄O, was obtained as the product of the reaction of 3,5-dibromosalicylaldehyde with 4-nitrobenzohydrazide in methanol. The benzohydrazide molecule is nearly planar, with a maximum deviation of 0.126 (2) Å. The mean planes of the two benzene rings make a dihedral angle of 9.3 (3)°. Intramolecular O—H⋯N and O—H⋯Br interactions are observed in the benzohydrazide molecule. In the crystal, pairs of adjacent benzohydrazide molecules are linked by two methanol molecules through intermolecular O—H⋯O and N—H⋯O hydrogen bonds, forming a dimer.

Related literature

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011 ); Horiuchi et al. (2009 ). For coordination compounds involving benzohydrazides, see: El-Dissouky et al. (2010 ); Zhang et al. (2010 ). For standard bond lengths, see: Allen et al. (1987 ). For related structures, see: Suleiman Gwaram et al. (2010 ); Dai & Mao (2010 ); Ban (2010 ).

Experimental

Crystal data

C₁₄H₉Br₂N₃O₄·CH₄O
M_r = 475.10
Monoclinic, P 2₁ /c
a = 7.576 (2) Å
b = 13.602 (2) Å
c = 17.230 (3) Å
β = 106.816 (3)°
V = 1699.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 4.80 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.327, T_max = 0.357
10168 measured reflections
3685 independent reflections
2011 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.103
S = 1.00
3685 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.52 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	1.94	2.642 (5)	143
N2—H2⋯O5ⁱ	0.90	1.91	2.800 (5)	169
O5—H5⋯O2ⁱⁱ	0.82	2.24	2.991 (6)	153
O5—H5⋯Br2	0.82	3.09	3.708 (4)	134
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811031187/qm2019sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031187/qm2019Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031187/qm2019Isup3.cml

checkCIF report

Comment top

Benzohydrazide compounds are well known for their biological activities (El-Sayed et al., 2011; Horiuchi et al., 2009). In addition, benzohydrazide compounds have also been used as versatile ligands in coordination chemistry (El-Dissouky et al., 2010). As a contribution to a structural study on hydrazone compounds, we present here the crystal structure of the title compound.

The compound contains a benzohydrazide molecule and a methanol molecule, as shown in Fig. 1. The bond distances and angles are within normal ranges (Allen et al., 1987) and are agree well with the corresponding bond distances and angles reported in closely related compounds (Suleiman Gwaram et al., 2010; Dai & Mao, 2010; Ban, 2010). The benzohydrazide molecule is nearly planar, with a maximum deviation of 0.126 (2) Å. The mean planes of the two benzene rings make a dihedral angle of 9.3 (3)°.

In the crystal structure of the title compound, the adjacent two benzohydrazide molecules are linked by two methanol molecules through intermolecular O—H···O and N—H···O hydrogen bonds, to form a dimer (Table 1, Fig. 2).

Related literature top

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011); Horiuchi et al. (2009). For coordination compounds involving benzohydrazides, see: El-Dissouky et al. (2010); Zhang et al. (2010). For standard bond lengths, see: Allen et al. (1987). For similar compounds, see: Suleiman Gwaram et al. (2010); Dai & Mao (2010); Ban (2010).

Experimental top

To a methanol solution (20 ml) of 3,5-dibromosalicylaldehyde (0.1 mmol, 28.0 mg) and 4-nitrobenzohydrazide (0.1 mmol, 18.1 mg), a few drops of acetic acid were added. The mixture was refluxed for 1 h and then cooled to room temperature. The white crystalline solid was collected by filtration, washed with cold methanol and dried in air. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution of the product in air.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not related to the hydrogen bonding are omitted for clarity.

N'-(3,5-Dibromo-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol monosolvate top

Crystal data top

C₁₄H₉Br₂N₃O₄·CH₄O	F(000) = 936
M_r = 475.10	D_x = 1.857 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.576 (2) Å	Cell parameters from 1293 reflections
b = 13.602 (2) Å	θ = 2.5–24.5°
c = 17.230 (3) Å	µ = 4.80 mm⁻¹
β = 106.816 (3)°	T = 298 K
V = 1699.6 (6) Å³	Block, yellow
Z = 4	0.30 × 0.27 × 0.27 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3685 independent reflections
Radiation source: fine-focus sealed tube	2011 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ω scans	θ_max = 27.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
T_min = 0.327, T_max = 0.357	k = −15→17
10168 measured reflections	l = −22→13

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) = 0.103	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.P)²] where P = (F_o² + 2F_c²)/3
3685 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₄H₉Br₂N₃O₄·CH₄O	V = 1699.6 (6) Å³
M_r = 475.10	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.576 (2) Å	µ = 4.80 mm⁻¹
b = 13.602 (2) Å	T = 298 K
c = 17.230 (3) Å	0.30 × 0.27 × 0.27 mm
β = 106.816 (3)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3685 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2011 reflections with I > 2σ(I)
T_min = 0.327, T_max = 0.357	R_int = 0.075
10168 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.00	Δρ_max = 0.53 e Å⁻³
3685 reflections	Δρ_min = −0.52 e Å⁻³
227 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	0.83099 (8)	1.22176 (4)	0.84550 (4)	0.0533 (2)
Br2	0.79926 (8)	0.82702 (4)	0.94026 (3)	0.0492 (2)
O1	0.5709 (5)	1.1483 (2)	0.6907 (2)	0.0470 (10)
H1	0.5200	1.1265	0.6454	0.056*
O2	0.2149 (5)	1.1321 (3)	0.4660 (2)	0.0584 (11)
O3	−0.3295 (6)	0.8090 (4)	0.1561 (3)	0.0822 (16)
O4	−0.3194 (7)	0.9500 (4)	0.1026 (3)	0.0953 (17)
N1	0.3873 (5)	1.0128 (3)	0.5892 (2)	0.0384 (11)
N2	0.2818 (5)	0.9780 (3)	0.5145 (2)	0.0404 (11)
H2	0.3046	0.9146	0.5048	0.048*
N3	−0.2750 (6)	0.8932 (5)	0.1592 (3)	0.0576 (15)
C1	0.5601 (6)	0.9761 (3)	0.7247 (3)	0.0320 (12)
C2	0.6184 (6)	1.0736 (4)	0.7435 (3)	0.0321 (12)
C3	0.7351 (6)	1.0935 (4)	0.8209 (3)	0.0355 (13)
C4	0.7889 (6)	1.0222 (4)	0.8791 (3)	0.0383 (13)
H4	0.8662	1.0374	0.9303	0.046*
C5	0.7259 (6)	0.9266 (4)	0.8603 (3)	0.0355 (12)
C6	0.6146 (6)	0.9041 (3)	0.7845 (3)	0.0347 (12)
H6	0.5747	0.8397	0.7727	0.042*
C7	0.4506 (7)	0.9483 (4)	0.6443 (3)	0.0388 (13)
H7	0.4256	0.8821	0.6323	0.047*
C8	0.1984 (7)	1.0439 (4)	0.4568 (3)	0.0365 (13)
C9	0.0789 (6)	0.9994 (4)	0.3795 (3)	0.0326 (12)
C10	0.0309 (7)	1.0598 (4)	0.3111 (3)	0.0397 (13)
H10	0.0768	1.1235	0.3141	0.048*
C11	−0.0849 (7)	1.0247 (4)	0.2391 (3)	0.0429 (14)
H11	−0.1175	1.0645	0.1932	0.052*
C12	−0.1505 (7)	0.9317 (4)	0.2361 (3)	0.0417 (14)
C13	−0.1068 (7)	0.8708 (4)	0.3030 (3)	0.0498 (15)
H13	−0.1535	0.8072	0.2993	0.060*
C14	0.0068 (7)	0.9054 (4)	0.3751 (3)	0.0419 (14)
H14	0.0352	0.8656	0.4209	0.050*
O5	0.4000 (5)	0.7107 (3)	0.9877 (2)	0.0612 (11)
H5	0.5128	0.7097	0.9988	0.073*
C15	0.3336 (8)	0.8036 (4)	0.9540 (4)	0.0627 (18)
H15A	0.3740	0.8154	0.9069	0.094*
H15B	0.3807	0.8542	0.9934	0.094*
H15C	0.2013	0.8039	0.9389	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0592 (4)	0.0348 (4)	0.0627 (4)	−0.0076 (3)	0.0125 (3)	−0.0113 (3)
Br2	0.0522 (4)	0.0489 (4)	0.0435 (4)	0.0081 (3)	0.0087 (3)	0.0129 (3)
O1	0.064 (2)	0.031 (2)	0.038 (2)	0.0028 (18)	0.0037 (19)	0.0001 (17)
O2	0.086 (3)	0.027 (2)	0.050 (3)	0.004 (2)	−0.001 (2)	−0.0070 (19)
O3	0.072 (3)	0.088 (4)	0.073 (3)	−0.020 (3)	0.000 (3)	−0.039 (3)
O4	0.111 (4)	0.104 (4)	0.042 (3)	0.017 (3)	−0.023 (3)	−0.004 (3)
N1	0.035 (2)	0.043 (3)	0.034 (3)	0.001 (2)	0.006 (2)	−0.008 (2)
N2	0.051 (3)	0.033 (3)	0.033 (3)	0.004 (2)	0.006 (2)	−0.007 (2)
N3	0.042 (3)	0.086 (5)	0.037 (3)	0.010 (3)	−0.001 (3)	−0.022 (3)
C1	0.032 (3)	0.028 (3)	0.034 (3)	−0.001 (2)	0.007 (2)	−0.001 (2)
C2	0.032 (3)	0.034 (3)	0.029 (3)	0.008 (2)	0.008 (2)	0.005 (2)
C3	0.033 (3)	0.032 (3)	0.042 (3)	−0.002 (2)	0.013 (3)	−0.007 (2)
C4	0.032 (3)	0.044 (4)	0.032 (3)	0.003 (2)	−0.001 (2)	−0.010 (3)
C5	0.035 (3)	0.033 (3)	0.037 (3)	0.003 (2)	0.008 (3)	0.005 (2)
C6	0.040 (3)	0.026 (3)	0.037 (3)	−0.001 (2)	0.011 (3)	−0.002 (2)
C7	0.045 (3)	0.035 (3)	0.035 (3)	−0.001 (3)	0.010 (3)	−0.005 (3)
C8	0.036 (3)	0.039 (4)	0.034 (3)	0.002 (3)	0.009 (3)	−0.003 (3)
C9	0.035 (3)	0.029 (3)	0.035 (3)	0.007 (2)	0.013 (3)	0.000 (2)
C10	0.044 (3)	0.035 (3)	0.039 (3)	0.008 (3)	0.010 (3)	−0.002 (3)
C11	0.045 (3)	0.053 (4)	0.031 (3)	0.015 (3)	0.011 (3)	0.009 (3)
C12	0.029 (3)	0.057 (4)	0.037 (3)	0.000 (3)	0.006 (3)	−0.012 (3)
C13	0.058 (4)	0.043 (4)	0.043 (4)	−0.006 (3)	0.006 (3)	−0.004 (3)
C14	0.045 (3)	0.037 (3)	0.038 (3)	−0.004 (3)	0.004 (3)	0.003 (3)
O5	0.050 (2)	0.056 (3)	0.070 (3)	−0.007 (2)	0.004 (2)	0.014 (2)
C15	0.058 (4)	0.048 (4)	0.079 (5)	0.002 (3)	0.015 (4)	0.007 (3)

Geometric parameters (Å, º) top

Br1—C3	1.890 (5)	C5—C6	1.368 (6)
Br2—C5	1.898 (5)	C6—H6	0.9300
O1—C2	1.341 (5)	C7—H7	0.9300
O1—H1	0.8200	C8—C9	1.505 (6)
O2—C8	1.212 (5)	C9—C14	1.383 (6)
O3—N3	1.214 (6)	C9—C10	1.396 (6)
O4—N3	1.213 (6)	C10—C11	1.381 (7)
N1—C7	1.280 (6)	C10—H10	0.9300
N1—N2	1.389 (5)	C11—C12	1.355 (7)
N2—C8	1.352 (6)	C11—H11	0.9300
N2—H2	0.9035	C12—C13	1.379 (7)
N3—C12	1.483 (6)	C13—C14	1.374 (7)
C1—C6	1.395 (6)	C13—H13	0.9300
C1—C2	1.406 (6)	C14—H14	0.9300
C1—C7	1.444 (6)	O5—C15	1.420 (6)
C2—C3	1.398 (6)	O5—H5	0.8200
C3—C4	1.369 (6)	C15—H15A	0.9600
C4—C5	1.390 (6)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600

C2—O1—H1	109.4	O2—C8—N2	123.5 (5)
C7—N1—N2	116.4 (4)	O2—C8—C9	121.8 (5)
C8—N2—N1	118.5 (4)	N2—C8—C9	114.7 (5)
C8—N2—H2	124.8	C14—C9—C10	119.7 (5)
N1—N2—H2	114.0	C14—C9—C8	123.2 (5)
O4—N3—O3	123.7 (5)	C10—C9—C8	117.0 (5)
O4—N3—C12	116.8 (6)	C11—C10—C9	119.8 (5)
O3—N3—C12	119.5 (6)	C11—C10—H10	120.1
C6—C1—C2	119.1 (4)	C9—C10—H10	120.1
C6—C1—C7	119.3 (5)	C12—C11—C10	119.2 (5)
C2—C1—C7	121.5 (4)	C12—C11—H11	120.4
O1—C2—C3	118.2 (4)	C10—C11—H11	120.4
O1—C2—C1	123.6 (4)	C11—C12—C13	122.2 (5)
C3—C2—C1	118.2 (4)	C11—C12—N3	119.6 (5)
C4—C3—C2	122.2 (5)	C13—C12—N3	118.2 (5)
C4—C3—Br1	118.4 (4)	C14—C13—C12	119.1 (5)
C2—C3—Br1	119.3 (4)	C14—C13—H13	120.5
C3—C4—C5	118.9 (4)	C12—C13—H13	120.5
C3—C4—H4	120.6	C13—C14—C9	120.0 (5)
C5—C4—H4	120.6	C13—C14—H14	120.0
C6—C5—C4	120.5 (4)	C9—C14—H14	120.0
C6—C5—Br2	120.2 (4)	C15—O5—H5	109.4
C4—C5—Br2	119.3 (4)	O5—C15—H15A	109.5
C5—C6—C1	121.1 (5)	O5—C15—H15B	109.5
C5—C6—H6	119.4	H15A—C15—H15B	109.5
C1—C6—H6	119.4	O5—C15—H15C	109.5
N1—C7—C1	121.3 (5)	H15A—C15—H15C	109.5
N1—C7—H7	119.4	H15B—C15—H15C	109.5
C1—C7—H7	119.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.94	2.642 (5)	143
N2—H2···O5ⁱ	0.90	1.91	2.800 (5)	169
O5—H5···O2ⁱⁱ	0.82	2.24	2.991 (6)	153
O5—H5···Br2	0.82	3.09	3.708 (4)	134

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₉Br₂N₃O₄·CH₄O
M_r	475.10
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.576 (2), 13.602 (2), 17.230 (3)
β (°)	106.816 (3)
V (Å³)	1699.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.80
Crystal size (mm)	0.30 × 0.27 × 0.27

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.327, 0.357
No. of measured, independent and observed [I > 2σ(I)] reflections	10168, 3685, 2011
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.103, 1.00
No. of reflections	3685
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.52

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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	1.94	2.642 (5)	142.6
N2—H2···O5ⁱ	0.90	1.91	2.800 (5)	169.1
O5—H5···O2ⁱⁱ	0.82	2.24	2.991 (6)	152.5
O5—H5···Br2	0.82	3.09	3.708 (4)	134.3

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, y−1/2, −z+3/2.

Acknowledgements

This project was sponsored by the Natural Development Foundation of Hebei Province (B2011204051), the Development Foundation of the Department of Education of Hebei Province (2010137) and the Research Development Foundation of the Agricultural University of Hebei.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orphen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Ban, H.-Y. (2010). Acta Cryst. E66, o3240. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dai, C.-H. & Mao, F.-L. (2010). Acta Cryst. E66, o2942. Web of Science CSD CrossRef IUCr Journals Google Scholar
El-Dissouky, A., Al-Fulaij, O., Awad, M. K. & Rizk, S. (2010). J. Coord. Chem. 63, 330–345. Web of Science CrossRef CAS Google Scholar
El-Sayed, M. A. A., Abdel-Aziz, N. I., Abdel-Aziz, A. A. M., El-Azab, A. S., Asiri, Y. A. & ElTahir, K. E. H. (2011). Bioorg. Med. Chem. 19, 3416–3424. Web of Science CAS PubMed Google Scholar
Horiuchi, T., Nagata, M., KitagawaB, M., Akahane, K. & Uoto, K. (2009). Bioorg. Med. Chem. 17, 7850–7860. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suleiman Gwaram, N., Khaledi, H., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2010). Acta Cryst. E66, o721. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, S.-P., Wei, Y. & Shao, S.-C. (2010). Acta Cryst. E66, m1635. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Page o2275

doi:10.1107/S1600536811031187

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-(3,5-Di­bromo-2-hy­dr­oxy­benzyl­­idene)-4-nitro­benzohydrazide methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(3,5-Dibromo-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol monosolvate