3-Bromo-N′-(3,5-dibromo-2-hydroxy­benzyl­idene)benzohydrazide methanol solvate

Wei, Y.-J.; Wang, F.-W.; Zhu, Q.-Y.

doi:10.1107/S1600536809007466

organic compounds

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Volume 65| Part 4| April 2009| Page o688

doi:10.1107/S1600536809007466

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3-Bromo-N′-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide methanol solvate

Yi-Jun Wei,^a ^* Feng-Wu Wang ^a and Qi-Yong Zhu ^a

^aDepartment of Chemistry, Huainan Normal College, Huainan 232001, People's Republic of China
^*Correspondence e-mail: huainanweiyijun@163.com

(Received 28 February 2009; accepted 28 February 2009; online 6 March 2009)

The title compound, C₁₄H₉Br₃N₂O₂·CH₄O, was prepared by the reaction of 3,5-dibromo-2-hydroxybenzaldehyde and 3-bromobenzohydrazide in methanol. The asymmetric unit of the crystal consists of a Schiff base molecule and a methanol molecule of crystallization. The dihedral angle between the two benzene rings is 5.5 (2)°. An intramolecular O—H⋯N hydrogen bond is observed. In the crystal structure, pairs of adjacent Schiff base molecules are linked by two methanol molecules through intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the synthesis of Schiff bases, see: Annigeri et al. (2002 ); Lodeiro et al. (2003 ); Rao et al. (2003 ). For related structures, see: Bao & Wei (2008 ); Odabaşoğlu et al. (2007 ); Wang et al. (2006 ); Wei et al. (2008 ); Yathirajan et al. (2007 ); Yehye et al. (2008 ); Zhu et al. (2009 ).

Experimental

Crystal data

C₁₄H₉Br₃N₂O₂·CH₄O
M_r = 509.00
Triclinic, $[P \overline 1]$
a = 8.900 (1) Å
b = 9.366 (1) Å
c = 11.392 (2) Å
α = 95.043 (2)°
β = 111.048 (2)°
γ = 99.584 (2)°
V = 862.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 7.03 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.216, T_max = 0.245
5016 measured reflections
3606 independent reflections
2582 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.084
S = 1.03
3606 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.61 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	1.84	2.559 (3)	145
O3—H3⋯O2ⁱ	0.82	1.97	2.767 (4)	164
N2—H2⋯O3ⁱⁱ	0.90 (3)	1.986 (18)	2.848 (4)	160 (4)
Symmetry codes: (i) x, y, z+1; (ii) -x+2, -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 global, I. DOI: 10.1107/S1600536809007466/sj2587sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007466/sj2587Isup2.hkl

checkCIF report

Comment top

Schiff bases are readily synthesized by the reaction of aldehydes with primary amines (Lodeiro et al., 2003; Annigeri et al., 2002; Rao et al., 2003). We have previously reported some Schiff bases and their complexes (Wei et al., 2008; Wang et al., 2006). In this paper, the preparation and crystal structure of the new Schiff base title compound (I), Fig 1, is reported.

The C═N bond length in the title molecule is comparable with those observed in other Schiff bases (Yehye et al., 2008; Odabaşoğlu et al., 2007; Yathirajan et al., 2007). All bond lengths are within normal ranges and are comparable to those observed in the related compounds (Zhu et al., 2009; Bao & Wei, 2008). The dihedral angle between C1—C6 and C9—C14 phenyl rings is 5.5 (2)°, indicating that the molecule is nearly coplanar. An intramolecular O1—H1···N1 hydrogen bond is observed and may contribute to the overall planarity of the molecule.

In the crystal structure, pairs of adjacent Schiff base molecules are linked by two methanol molecules through intermolecular N2—H2···O3 and O3—H3···O2 hydrogen bonds, Table 1, Fig. 2.

Related literature top

For the synthesis of Schiff bases, see: Annigeri et al. (2002); Lodeiro et al. (2003); Rao et al. (2003). For related structures, see: Bao & Wei (2008); Odabaşoğlu et al. (2007); Wang et al. (2006); Wei et al. (2008); Yathirajan et al. (2007); Yehye et al. (2008); Zhu et al. (2009).

Experimental top

3,5-Dibromo-2-hydroxybenzaldehyde (1.0 mmol) and 3-bromobenzohydrazide (1.0 mmol) were dissolved in methanol (30 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. After keeping this solution in air for a week, colourless block-shaped crystals were formed.

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 title compound, showing 30% probability displacement ellipsoids. The dashed line indicates an intramolecular hydrogen bond.
	Fig. 2. Molecular packing of the title compound. Hydrogen bonds are shown as dashed lines.

(I) top

Crystal data top

C₁₄H₉Br₃N₂O₂·CH₄O	Z = 2
M_r = 509.00	F(000) = 492
Triclinic, P1	D_x = 1.960 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.900 (1) Å	Cell parameters from 1965 reflections
b = 9.366 (1) Å	θ = 2.5–28.0°
c = 11.392 (2) Å	µ = 7.03 mm⁻¹
α = 95.043 (2)°	T = 298 K
β = 111.048 (2)°	Block, colorless
γ = 99.584 (2)°	0.23 × 0.20 × 0.20 mm
V = 862.6 (2) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2582 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.216, T_max = 0.245	k = −11→11
5016 measured reflections	l = −12→14

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0368P)² + 0.2522P] where P = (F_o² + 2F_c²)/3
3606 reflections	(Δ/σ)_max = 0.001
214 parameters	Δρ_max = 0.45 e Å⁻³
1 restraint	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₁₄H₉Br₃N₂O₂·CH₄O	γ = 99.584 (2)°
M_r = 509.00	V = 862.6 (2) Å³
Triclinic, P1	Z = 2
a = 8.900 (1) Å	Mo Kα radiation
b = 9.366 (1) Å	µ = 7.03 mm⁻¹
c = 11.392 (2) Å	T = 298 K
α = 95.043 (2)°	0.23 × 0.20 × 0.20 mm
β = 111.048 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3606 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2582 reflections with I > 2σ(I)
T_min = 0.216, T_max = 0.245	R_int = 0.019
5016 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.45 e Å⁻³
3606 reflections	Δρ_min = −0.61 e Å⁻³
214 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	0.70334 (5)	1.00574 (5)	−0.37638 (4)	0.07063 (16)
Br2	1.39490 (6)	1.16831 (6)	−0.18075 (5)	0.08319 (19)
Br3	1.13101 (5)	0.31103 (4)	0.49994 (3)	0.05564 (13)
O1	0.7708 (3)	0.8094 (3)	−0.1804 (2)	0.0524 (6)
H1	0.7891	0.7546	−0.1269	0.079*
O2	0.6880 (3)	0.5145 (3)	−0.0140 (2)	0.0564 (7)
O3	0.7124 (3)	0.4000 (3)	0.7628 (2)	0.0634 (7)
H3	0.6886	0.4388	0.8192	0.095*
N1	0.9495 (3)	0.7027 (3)	0.0069 (2)	0.0402 (6)
N2	0.9553 (4)	0.6172 (3)	0.0991 (3)	0.0410 (6)
C1	1.0672 (4)	0.8813 (3)	−0.0850 (3)	0.0351 (7)
C2	0.9137 (4)	0.8887 (4)	−0.1748 (3)	0.0378 (7)
C3	0.9096 (4)	0.9860 (4)	−0.2607 (3)	0.0425 (8)
C4	1.0505 (4)	1.0671 (4)	−0.2633 (3)	0.0449 (8)
H4	1.0450	1.1288	−0.3236	0.054*
C5	1.2002 (4)	1.0569 (4)	−0.1762 (3)	0.0460 (8)
C6	1.2101 (4)	0.9668 (4)	−0.0856 (3)	0.0424 (8)
H6	1.3121	0.9632	−0.0251	0.051*
C7	1.0795 (4)	0.7865 (3)	0.0117 (3)	0.0389 (8)
H7	1.1807	0.7877	0.0755	0.047*
C8	0.8112 (4)	0.5247 (4)	0.0818 (3)	0.0388 (7)
C9	0.8101 (4)	0.4374 (3)	0.1852 (3)	0.0365 (7)
C10	0.6573 (4)	0.3690 (4)	0.1800 (3)	0.0487 (9)
H10	0.5620	0.3809	0.1160	0.058*
C11	0.6468 (5)	0.2827 (5)	0.2705 (4)	0.0607 (11)
H11	0.5442	0.2361	0.2670	0.073*
C12	0.7878 (5)	0.2654 (4)	0.3657 (4)	0.0538 (10)
H12	0.7811	0.2077	0.4268	0.065*
C13	0.9373 (4)	0.3341 (4)	0.3692 (3)	0.0407 (8)
C14	0.9518 (4)	0.4212 (3)	0.2807 (3)	0.0375 (7)
H14	1.0550	0.4679	0.2853	0.045*
C15	0.5947 (6)	0.4070 (6)	0.6437 (4)	0.0784 (14)
H15A	0.5748	0.5045	0.6420	0.118*
H15B	0.4939	0.3389	0.6291	0.118*
H15C	0.6346	0.3822	0.5784	0.118*
H2	1.054 (3)	0.617 (5)	0.159 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0520 (3)	0.0897 (3)	0.0683 (3)	0.0262 (2)	0.0085 (2)	0.0444 (2)
Br2	0.0529 (3)	0.0928 (4)	0.0939 (4)	−0.0098 (2)	0.0193 (2)	0.0505 (3)
Br3	0.0528 (2)	0.0679 (3)	0.0421 (2)	0.01579 (19)	0.00793 (17)	0.02572 (18)
O1	0.0349 (13)	0.0634 (17)	0.0562 (15)	0.0067 (11)	0.0111 (12)	0.0302 (13)
O2	0.0364 (14)	0.0847 (19)	0.0458 (14)	0.0112 (13)	0.0087 (12)	0.0325 (13)
O3	0.0423 (15)	0.087 (2)	0.0534 (15)	0.0155 (14)	0.0067 (13)	0.0188 (15)
N1	0.0430 (16)	0.0410 (16)	0.0396 (14)	0.0114 (13)	0.0152 (13)	0.0199 (12)
N2	0.0402 (16)	0.0463 (16)	0.0387 (15)	0.0110 (13)	0.0132 (13)	0.0220 (13)
C1	0.0383 (18)	0.0363 (17)	0.0315 (16)	0.0076 (14)	0.0131 (14)	0.0099 (13)
C2	0.0372 (18)	0.0398 (18)	0.0363 (17)	0.0108 (15)	0.0117 (15)	0.0102 (14)
C3	0.042 (2)	0.047 (2)	0.0378 (18)	0.0150 (16)	0.0109 (16)	0.0151 (15)
C4	0.052 (2)	0.043 (2)	0.0396 (18)	0.0100 (17)	0.0146 (17)	0.0175 (15)
C5	0.044 (2)	0.044 (2)	0.049 (2)	0.0008 (16)	0.0177 (17)	0.0164 (16)
C6	0.0371 (18)	0.0434 (19)	0.0422 (18)	0.0056 (15)	0.0094 (15)	0.0138 (15)
C7	0.0406 (19)	0.0391 (19)	0.0357 (17)	0.0119 (15)	0.0094 (15)	0.0144 (14)
C8	0.0369 (18)	0.0457 (19)	0.0398 (18)	0.0155 (15)	0.0159 (16)	0.0195 (15)
C9	0.0392 (18)	0.0391 (18)	0.0346 (16)	0.0115 (14)	0.0151 (15)	0.0124 (14)
C10	0.0339 (19)	0.061 (2)	0.054 (2)	0.0124 (17)	0.0155 (17)	0.0246 (18)
C11	0.042 (2)	0.077 (3)	0.073 (3)	0.0102 (19)	0.028 (2)	0.039 (2)
C12	0.052 (2)	0.062 (2)	0.059 (2)	0.0154 (19)	0.0278 (19)	0.0336 (19)
C13	0.0411 (19)	0.046 (2)	0.0342 (16)	0.0104 (16)	0.0113 (15)	0.0130 (15)
C14	0.0329 (17)	0.0427 (19)	0.0374 (17)	0.0066 (14)	0.0135 (14)	0.0118 (14)
C15	0.052 (3)	0.115 (4)	0.056 (2)	0.010 (3)	0.005 (2)	0.034 (3)

Geometric parameters (Å, º) top

Br1—C3	1.886 (3)	C4—H4	0.9300
Br2—C5	1.889 (3)	C5—C6	1.378 (4)
Br3—C13	1.891 (3)	C6—H6	0.9300
O1—C2	1.339 (4)	C7—H7	0.9300
O1—H1	0.8200	C8—C9	1.494 (4)
O2—C8	1.221 (4)	C9—C14	1.381 (4)
O3—C15	1.400 (4)	C9—C10	1.381 (5)
O3—H3	0.8200	C10—C11	1.385 (5)
N1—C7	1.265 (4)	C10—H10	0.9300
N1—N2	1.367 (3)	C11—C12	1.378 (5)
N2—C8	1.361 (4)	C11—H11	0.9300
N2—H2	0.90 (3)	C12—C13	1.364 (5)
C1—C6	1.388 (5)	C12—H12	0.9300
C1—C2	1.399 (4)	C13—C14	1.378 (4)
C1—C7	1.461 (4)	C14—H14	0.9300
C2—C3	1.390 (4)	C15—H15A	0.9600
C3—C4	1.365 (5)	C15—H15B	0.9600
C4—C5	1.370 (5)	C15—H15C	0.9600

C2—O1—H1	109.5	O2—C8—N2	121.2 (3)
C15—O3—H3	109.5	O2—C8—C9	121.5 (3)
C7—N1—N2	120.2 (3)	N2—C8—C9	117.2 (3)
C8—N2—N1	115.8 (3)	C14—C9—C10	120.4 (3)
C8—N2—H2	125 (3)	C14—C9—C8	123.2 (3)
N1—N2—H2	118 (3)	C10—C9—C8	116.4 (3)
C6—C1—C2	120.0 (3)	C9—C10—C11	119.6 (3)
C6—C1—C7	119.1 (3)	C9—C10—H10	120.2
C2—C1—C7	120.8 (3)	C11—C10—H10	120.2
O1—C2—C3	118.5 (3)	C12—C11—C10	120.3 (3)
O1—C2—C1	123.4 (3)	C12—C11—H11	119.8
C3—C2—C1	118.1 (3)	C10—C11—H11	119.8
C4—C3—C2	121.7 (3)	C13—C12—C11	119.0 (3)
C4—C3—Br1	119.5 (2)	C13—C12—H12	120.5
C2—C3—Br1	118.8 (3)	C11—C12—H12	120.5
C3—C4—C5	119.5 (3)	C12—C13—C14	122.0 (3)
C3—C4—H4	120.2	C12—C13—Br3	119.2 (3)
C5—C4—H4	120.2	C14—C13—Br3	118.8 (2)
C4—C5—C6	120.8 (3)	C13—C14—C9	118.6 (3)
C4—C5—Br2	119.4 (3)	C13—C14—H14	120.7
C6—C5—Br2	119.8 (3)	C9—C14—H14	120.7
C5—C6—C1	119.7 (3)	O3—C15—H15A	109.5
C5—C6—H6	120.2	O3—C15—H15B	109.5
C1—C6—H6	120.2	H15A—C15—H15B	109.5
N1—C7—C1	118.6 (3)	O3—C15—H15C	109.5
N1—C7—H7	120.7	H15A—C15—H15C	109.5
C1—C7—H7	120.7	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.559 (3)	145
O3—H3···O2ⁱ	0.82	1.97	2.767 (4)	164
N2—H2···O3ⁱⁱ	0.90 (3)	1.99 (2)	2.848 (4)	160 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₉Br₃N₂O₂·CH₄O
M_r	509.00
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.900 (1), 9.366 (1), 11.392 (2)
α, β, γ (°)	95.043 (2), 111.048 (2), 99.584 (2)
V (Å³)	862.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	7.03
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.216, 0.245
No. of measured, independent and observed [I > 2σ(I)] reflections	5016, 3606, 2582
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.084, 1.03
No. of reflections	3606
No. of parameters	214
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)	0.45, −0.61

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	1.84	2.559 (3)	145.1
O3—H3···O2ⁱ	0.82	1.97	2.767 (4)	163.6
N2—H2···O3ⁱⁱ	0.90 (3)	1.986 (18)	2.848 (4)	160 (4)

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

Acknowledgements

The authors thank the Natural Science Foundation of the Education Office of Anhui Province, China, for financial support (grant No. KJ2007A126ZC).

References

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Volume 65| Part 4| April 2009| Page o688

doi:10.1107/S1600536809007466

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

3-Bromo-N′-(3,5-di­bromo-2-hy­droxy­benzyl­­idene)benzohydrazide methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Bromo-N′-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide methanol solvate