N′-(5-Bromo-2-hy­droxy­benzyl­idene)-3-nitro­benzohydrazide methanol mono­solvate

Tang, C.-B.

doi:10.1107/S1600536811042553

organic compounds

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Volume 67| Part 11| November 2011| Page o3002

doi:10.1107/S1600536811042553

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N′-(5-Bromo-2-hydroxybenzylidene)-3-nitrobenzohydrazide methanol monosolvate

Chun-Bao Tang ^a ^*

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

(Received 10 October 2011; accepted 14 October 2011; online 22 October 2011)

In the title compound, C₁₄H₁₀BrN₃O₄·CH₄O, the dihedral angle between the two benzene rings in the hydrazone molecule is 5.8 (3)° and an intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. An O—H⋯O hydrogen bond occurs between the hydrazone molecule and the methanol solvent molecule. In the crystal, the components are linked by intermolecular N—H⋯O hydrogen bonds, forming chains along the a 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 , 2011 ). For reference bond-length data, see: Allen et al. (1987 ) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₀BrN₃O₄·CH₄O
M_r = 396.20
Triclinic, $[P \overline 1]$
a = 6.701 (2) Å
b = 9.492 (3) Å
c = 13.011 (3) Å
α = 105.866 (2)°
β = 92.535 (2)°
γ = 94.496 (2)°
V = 791.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.63 mm⁻¹
T = 298 K
0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.726, T_max = 0.779
6325 measured reflections
3356 independent reflections
1142 reflections with I > 2σ(I)
R_int = 0.109

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.236
S = 0.93
3356 reflections
223 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5ⁱ	0.90 (1)	2.04 (5)	2.854 (10)	150 (9)
O5—H5⋯O2	0.82	1.90	2.701 (10)	166
O1—H1⋯N1	0.82	1.99	2.700 (10)	144
Symmetry code: (i) x+1, y, 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811042553/qm2037sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042553/qm2037Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811042553/qm2037Isup3.cml

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 title new hydrazone compound (Fig. 1).

The compound contains a hydrazone molecule and a methanol molecule of crystallization. The dihedral angle between the two benzene rings in the hydrazone molecule is 5.8 (3)°. An intramolecular O—H···N hydrogen bond generates a S(6) ring motif in the hydrazone molecule (Bernstein et al., 1995). Bond lengths in the compound are normal (Allen et al., 1987) and comparable to those in the similar compounds the author has reported previously (Tang, 2010; Tang, 2011). In the crystal structure, the hydrazone molecules are linked by the methanol molecules through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the a 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, 2011). For reference bond-length data, see: Allen et al. (1987) and for hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

5-Bromo-2-hydroxybenzaldehyde (0.1 mmol, 20.1 mg) and 3-nitrobenzohydrazide (0.1 mmol, 18.1 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear yellow solution. Yellow needle-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.

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 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 and hydrogen bonds are drawn as dashed lines.
	Fig. 2. Molecular packing of the title compound, with hydrogen bonds shown as dashed lines.

N'-(5-Bromo-2-hydroxybenzylidene)-3-nitrobenzohydrazide methanol monosolvate top

Crystal data top

C₁₄H₁₀BrN₃O₄·CH₄O	Z = 2
M_r = 396.20	F(000) = 400
Triclinic, P1	D_x = 1.662 Mg m⁻³
a = 6.701 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.492 (3) Å	Cell parameters from 850 reflections
c = 13.011 (3) Å	θ = 2.6–24.3°
α = 105.866 (2)°	µ = 2.63 mm⁻¹
β = 92.535 (2)°	T = 298 K
γ = 94.496 (2)°	Cut from needle, yellow
V = 791.7 (4) Å³	0.13 × 0.12 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3356 independent reflections
Radiation source: fine-focus sealed tube	1142 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.109
ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.726, T_max = 0.779	k = −12→11
6325 measured reflections	l = −16→16

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.236	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ²(F_o²) + (0.0975P)²] where P = (F_o² + 2F_c²)/3
3356 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.56 e Å⁻³
1 restraint	Δρ_min = −0.83 e Å⁻³

Crystal data top

C₁₄H₁₀BrN₃O₄·CH₄O	γ = 94.496 (2)°
M_r = 396.20	V = 791.7 (4) Å³
Triclinic, P1	Z = 2
a = 6.701 (2) Å	Mo Kα radiation
b = 9.492 (3) Å	µ = 2.63 mm⁻¹
c = 13.011 (3) Å	T = 298 K
α = 105.866 (2)°	0.13 × 0.12 × 0.10 mm
β = 92.535 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3356 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1142 reflections with I > 2σ(I)
T_min = 0.726, T_max = 0.779	R_int = 0.109
6325 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	1 restraint
wR(F²) = 0.236	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	Δρ_max = 0.56 e Å⁻³
3356 reflections	Δρ_min = −0.83 e Å⁻³
223 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	0.86686 (17)	−0.35734 (12)	−0.00940 (10)	0.0719 (6)
N1	0.6581 (10)	0.3028 (8)	0.2164 (6)	0.048 (2)
N2	0.7644 (11)	0.4381 (8)	0.2533 (7)	0.053 (2)
N3	0.6919 (17)	1.0932 (11)	0.4149 (7)	0.065 (3)
O1	0.3298 (9)	0.1075 (7)	0.1801 (6)	0.065 (2)
H1	0.3900	0.1899	0.2010	0.097*
O2	0.4839 (9)	0.5566 (7)	0.2601 (7)	0.075 (2)
O3	0.5095 (13)	1.0768 (8)	0.4134 (7)	0.083 (3)
O4	0.7862 (12)	1.2078 (9)	0.4478 (7)	0.095 (3)
O5	0.1684 (10)	0.3998 (8)	0.3110 (8)	0.080 (2)
H5	0.2535	0.4451	0.2858	0.119*
C1	0.6692 (13)	0.0452 (9)	0.1409 (7)	0.040 (2)
C2	0.4602 (13)	0.0083 (10)	0.1402 (7)	0.045 (3)
C3	0.3811 (13)	−0.1355 (10)	0.0995 (8)	0.052 (3)
H3	0.2446	−0.1599	0.1019	0.062*
C4	0.5030 (15)	−0.2441 (10)	0.0548 (8)	0.058 (3)
H4	0.4491	−0.3409	0.0255	0.069*
C5	0.7013 (14)	−0.2068 (10)	0.0547 (8)	0.051 (3)
C6	0.7845 (13)	−0.0647 (10)	0.0954 (7)	0.045 (3)
H6	0.9214	−0.0428	0.0920	0.054*
C7	0.7583 (13)	0.1925 (10)	0.1837 (8)	0.049 (3)
H7	0.8975	0.2089	0.1880	0.058*
C8	0.6684 (15)	0.5605 (10)	0.2710 (8)	0.050 (3)
C9	0.7917 (13)	0.7039 (10)	0.3036 (8)	0.047 (3)
C10	0.6934 (13)	0.8259 (11)	0.3455 (7)	0.048 (3)
H10	0.5569	0.8164	0.3553	0.058*
C11	0.7981 (15)	0.9610 (10)	0.3723 (8)	0.050 (3)
C12	1.0014 (16)	0.9800 (12)	0.3593 (8)	0.061 (3)
H12	1.0697	1.0735	0.3782	0.073*
C13	1.0973 (15)	0.8607 (13)	0.3191 (9)	0.069 (3)
H13	1.2341	0.8716	0.3102	0.082*
C14	0.9956 (14)	0.7203 (12)	0.2903 (8)	0.060 (3)
H14	1.0640	0.6382	0.2623	0.071*
C15	0.2258 (18)	0.4128 (14)	0.4176 (12)	0.100 (5)
H15A	0.2783	0.5124	0.4524	0.149*
H15B	0.3272	0.3478	0.4208	0.149*
H15C	0.1116	0.3873	0.4530	0.149*
H2	0.893 (5)	0.462 (11)	0.280 (8)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0633 (8)	0.0472 (7)	0.0991 (11)	0.0263 (5)	0.0049 (6)	0.0041 (6)
N1	0.037 (5)	0.039 (5)	0.066 (6)	0.010 (4)	−0.003 (4)	0.010 (4)
N2	0.037 (5)	0.034 (5)	0.079 (6)	0.006 (4)	−0.003 (4)	−0.001 (4)
N3	0.078 (7)	0.050 (6)	0.065 (7)	0.014 (6)	−0.008 (6)	0.011 (5)
O1	0.046 (4)	0.040 (4)	0.105 (6)	0.014 (3)	0.000 (4)	0.011 (4)
O2	0.027 (4)	0.058 (5)	0.138 (7)	0.009 (3)	−0.002 (4)	0.027 (5)
O3	0.072 (6)	0.063 (5)	0.116 (7)	0.032 (4)	0.010 (5)	0.018 (5)
O4	0.089 (6)	0.045 (5)	0.133 (8)	0.013 (5)	−0.015 (5)	−0.003 (5)
O5	0.041 (5)	0.057 (5)	0.135 (8)	0.006 (4)	−0.005 (5)	0.019 (5)
C1	0.033 (5)	0.035 (6)	0.053 (7)	0.006 (4)	0.000 (5)	0.013 (5)
C2	0.038 (6)	0.041 (6)	0.061 (7)	0.019 (5)	0.014 (5)	0.019 (5)
C3	0.034 (5)	0.037 (6)	0.080 (8)	0.003 (5)	0.001 (5)	0.009 (5)
C4	0.060 (7)	0.024 (5)	0.085 (9)	0.004 (5)	−0.008 (6)	0.009 (5)
C5	0.040 (6)	0.039 (6)	0.068 (8)	0.006 (5)	−0.003 (5)	0.005 (5)
C6	0.030 (5)	0.041 (6)	0.061 (7)	0.006 (4)	0.002 (5)	0.009 (5)
C7	0.033 (5)	0.052 (7)	0.064 (7)	0.012 (5)	−0.001 (5)	0.020 (6)
C8	0.045 (7)	0.042 (6)	0.065 (8)	0.016 (5)	0.003 (5)	0.014 (5)
C9	0.034 (6)	0.044 (6)	0.064 (7)	0.015 (5)	0.000 (5)	0.017 (5)
C10	0.034 (5)	0.059 (7)	0.055 (7)	0.018 (5)	0.002 (5)	0.017 (5)
C11	0.056 (7)	0.036 (6)	0.051 (7)	0.004 (5)	−0.004 (5)	0.002 (5)
C12	0.058 (8)	0.057 (7)	0.063 (8)	−0.002 (6)	−0.011 (6)	0.016 (6)
C13	0.039 (6)	0.072 (8)	0.088 (9)	0.011 (6)	−0.005 (6)	0.011 (7)
C14	0.035 (6)	0.064 (8)	0.069 (8)	0.006 (5)	−0.002 (5)	0.001 (6)
C15	0.087 (10)	0.090 (10)	0.109 (12)	0.017 (8)	−0.023 (9)	0.008 (9)

Geometric parameters (Å, º) top

Br1—C5	1.910 (9)	C4—C5	1.348 (12)
N1—C7	1.273 (10)	C4—H4	0.9300
N1—N2	1.370 (10)	C5—C6	1.370 (11)
N2—C8	1.342 (11)	C6—H6	0.9300
N2—H2	0.901 (10)	C7—H7	0.9300
N3—O4	1.175 (10)	C8—C9	1.481 (13)
N3—O3	1.219 (10)	C9—C10	1.370 (12)
N3—C11	1.477 (12)	C9—C14	1.387 (12)
O1—C2	1.349 (9)	C10—C11	1.360 (12)
O1—H1	0.8200	C10—H10	0.9300
O2—C8	1.235 (10)	C11—C12	1.384 (13)
O5—C15	1.392 (13)	C12—C13	1.338 (13)
O5—H5	0.8200	C12—H12	0.9300
C1—C6	1.366 (11)	C13—C14	1.393 (13)
C1—C2	1.416 (12)	C13—H13	0.9300
C1—C7	1.427 (12)	C14—H14	0.9300
C2—C3	1.375 (12)	C15—H15A	0.9600
C3—C4	1.383 (12)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600

C7—N1—N2	117.1 (8)	C1—C7—H7	118.2
C8—N2—N1	119.9 (8)	O2—C8—N2	122.4 (9)
C8—N2—H2	109 (7)	O2—C8—C9	119.9 (8)
N1—N2—H2	130 (7)	N2—C8—C9	117.7 (8)
O4—N3—O3	123.5 (10)	C10—C9—C14	119.5 (9)
O4—N3—C11	118.9 (10)	C10—C9—C8	116.8 (8)
O3—N3—C11	117.6 (9)	C14—C9—C8	123.7 (9)
C2—O1—H1	109.5	C11—C10—C9	119.1 (9)
C15—O5—H5	109.5	C11—C10—H10	120.4
C6—C1—C2	117.8 (8)	C9—C10—H10	120.4
C6—C1—C7	120.2 (8)	C10—C11—C12	122.3 (9)
C2—C1—C7	122.0 (8)	C10—C11—N3	119.4 (9)
O1—C2—C3	116.6 (8)	C12—C11—N3	118.3 (9)
O1—C2—C1	123.4 (8)	C13—C12—C11	118.4 (10)
C3—C2—C1	120.0 (8)	C13—C12—H12	120.8
C2—C3—C4	120.5 (9)	C11—C12—H12	120.8
C2—C3—H3	119.7	C12—C13—C14	121.1 (10)
C4—C3—H3	119.7	C12—C13—H13	119.5
C5—C4—C3	118.7 (9)	C14—C13—H13	119.5
C5—C4—H4	120.6	C9—C14—C13	119.5 (10)
C3—C4—H4	120.6	C9—C14—H14	120.2
C4—C5—C6	122.0 (9)	C13—C14—H14	120.2
C4—C5—Br1	118.2 (7)	O5—C15—H15A	109.5
C6—C5—Br1	119.7 (7)	O5—C15—H15B	109.5
C1—C6—C5	120.9 (8)	H15A—C15—H15B	109.5
C1—C6—H6	119.6	O5—C15—H15C	109.5
C5—C6—H6	119.6	H15A—C15—H15C	109.5
N1—C7—C1	123.7 (8)	H15B—C15—H15C	109.5
N1—C7—H7	118.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5ⁱ	0.90 (1)	2.04 (5)	2.854 (10)	150 (9)
O5—H5···O2	0.82	1.90	2.701 (10)	166
O1—H1···N1	0.82	1.99	2.700 (10)	144

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀BrN₃O₄·CH₄O
M_r	396.20
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.701 (2), 9.492 (3), 13.011 (3)
α, β, γ (°)	105.866 (2), 92.535 (2), 94.496 (2)
V (Å³)	791.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.63
Crystal size (mm)	0.13 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.726, 0.779
No. of measured, independent and observed [I > 2σ(I)] reflections	6325, 3356, 1142
R_int	0.109
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.236, 0.93
No. of reflections	3356
No. of parameters	223
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.83

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···O5ⁱ	0.901 (10)	2.04 (5)	2.854 (10)	150 (9)
O5—H5···O2	0.82	1.90	2.701 (10)	166.3
O1—H1···N1	0.82	1.99	2.700 (10)	144.3

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

Acknowledgements

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

References

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3002

doi:10.1107/S1600536811042553

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

N′-(5-Bromo-2-hy­dr­oxy­benzyl­­idene)-3-nitro­benzohydrazide methanol mono­solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(5-Bromo-2-hydroxybenzylidene)-3-nitrobenzohydrazide methanol monosolvate