N′-(5-Bromo-2-methoxy­benzyl­idene)-4-hydroxy­benzohydrazide methanol solvate

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

doi:10.1107/S1600536809022983

organic compounds

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Volume 65| Part 7| July 2009| Page o1650

doi:10.1107/S1600536809022983

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N′-(5-Bromo-2-methoxybenzylidene)-4-hydroxybenzohydrazide methanol solvate

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

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

(Received 13 June 2009; accepted 15 June 2009; online 20 June 2009)

In the title hydrazone compound, C₁₅H₁₃BrN₂O₃·CH₃OH, the methanol solvate is linked to the benzohydrazide molecule through O—H⋯N and O—H⋯O hydrogen bonds. The benzohydrazide molecule adopts an E configuration about the C=N double bond. The molecule is twisted, with a dihedral angle between the two substituted benzene rings of 35.7 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O and O—H⋯O hydrogen bonds, forming layers parallel to the ac plane.

Related literature

For the biological properties of the hydrazone compounds, see: Khattab (2005 ); Küçükgüzel et al. (2003 ); Çukurovalı et al. (2006 ). For the structures of hydrazone derivatives, 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

C₁₅H₁₃BrN₂O₃·CH₄O
M_r = 381.23
Orthorhombic, P b c a
a = 11.1886 (7) Å
b = 14.4464 (9) Å
c = 20.5927 (13) Å
V = 3328.5 (4) Å³
Z = 8
Mo Kα radiation
μ = 2.49 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.598, T_max = 0.636
19306 measured reflections
3638 independent reflections
2234 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.179
S = 1.06
3638 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.95 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⋯O3ⁱ	0.89 (4)	2.16 (5)	3.009 (4)	158 (5)
O4—H4⋯N1	0.82	2.64	3.239 (5)	131
O4—H4⋯O2	0.82	1.96	2.729 (4)	157
O3—H3⋯O4ⁱⁱ	0.82	1.78	2.602 (5)	175
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536809022983/at2817sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022983/at2817Isup2.hkl

checkCIF report

Comment top

Hydrazone and Schiff base compounds derived from the reaction of aldehydes with hydrazides have been widely investigated both for their crystal structures and biological properties (Khattab et al., 2005; Küçükgüzel et al., 2003; Çukurovalı et al., 2006). In the last few years, 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). However, the hydrazone compounds derived the 5-bromo-2-methoxybenzaldehyde have never been reported. In this paper, the crystal structure of the title new hydrazone compound, (I), derived from the reaction of 5-bromo-2-methoxybenzaldehyde and 4-hydroxybenzohydrazide, is reported.

The molecular structure of (I) is shown as Fig. 1. The compound consists of a hydrazone molecule and a methanol molecule of crystallization. The methanol molecule is linked to the hydrazone molecule through intramolecular O–H···N and O–H···O hydrogen bonds, Table 1. The hydrazone molecule adopts an E configuration about the C═N double bond. The molecule is twisted, with the dihedral angle between the C1—C6 and C10—C15 benzene rings of 35.7 (2)°. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure of the compound, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds, Table 1, forming layers parallel to the ac plane, as shown in Fig. 2.

Related literature top

For the biological properties of the hydrazone compounds, see: Khattab et al. (2005); Küçükgüzel et al. (2003); Çukurovalı et al. (2006). For the structures of hydrazone derivatives, 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

5-Bromo-2-methoxybenzaldehyde (1.0 mmol, 215.0 mg) and 4-hydroxybenzohydrazide (1.0 mmol, 152.2 mg) were mixed and refluxed in methanol (50 ml). The mixture was stirred for 1 h to give a clear colourless solution. Colourless crystals of (I) were formed by slow evaporation of the solution in air for a few 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of (I). Hydrogen atoms not involved in hydrogen bonding have been omitted. Hydrogen bonds are shown as dashed lines.

N'-(5-Bromo-2-methoxybenzylidene)-4-hydroxybenzohydrazide methanol solvate top

Crystal data top

C₁₅H₁₃BrN₂O₃·CH₄O	F(000) = 1552
M_r = 381.23	D_x = 1.522 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3350 reflections
a = 11.1886 (7) Å	θ = 2.5–24.5°
b = 14.4464 (9) Å	µ = 2.49 mm⁻¹
c = 20.5927 (13) Å	T = 298 K
V = 3328.5 (4) Å³	Block, colourless
Z = 8	0.23 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3638 independent reflections
Radiation source: fine-focus sealed tube	2234 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.598, T_max = 0.636	k = −18→15
19306 measured reflections	l = −23→26

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0849P)² + 4.4269P] where P = (F_o² + 2F_c²)/3
3638 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.95 e Å⁻³
1 restraint	Δρ_min = −0.83 e Å⁻³

Crystal data top

C₁₅H₁₃BrN₂O₃·CH₄O	V = 3328.5 (4) Å³
M_r = 381.23	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.1886 (7) Å	µ = 2.49 mm⁻¹
b = 14.4464 (9) Å	T = 298 K
c = 20.5927 (13) Å	0.23 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3638 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2234 reflections with I > 2σ(I)
T_min = 0.598, T_max = 0.636	R_int = 0.054
19306 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	1 restraint
wR(F²) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.95 e Å⁻³
3638 reflections	Δρ_min = −0.83 e Å⁻³
214 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	0.82955 (5)	0.03436 (5)	0.73273 (2)	0.0699 (3)
N1	0.7667 (3)	0.1520 (3)	0.48426 (15)	0.0388 (8)
N2	0.7226 (3)	0.1789 (3)	0.42463 (16)	0.0396 (8)
O1	1.1184 (3)	0.1179 (3)	0.49400 (17)	0.0591 (9)
O2	0.5326 (3)	0.1584 (2)	0.45803 (13)	0.0472 (8)
O3	0.4288 (3)	0.2326 (3)	0.16133 (13)	0.0499 (9)
H3	0.4694	0.2697	0.1408	0.075*
O4	0.5525 (4)	0.1537 (3)	0.59007 (15)	0.0589 (10)
H4	0.5657	0.1611	0.5512	0.088*
C1	0.9352 (4)	0.1136 (3)	0.54842 (19)	0.0365 (9)
C2	1.0590 (4)	0.0944 (3)	0.5493 (2)	0.0422 (10)
C3	1.1097 (4)	0.0555 (3)	0.6035 (2)	0.0488 (12)
H3A	1.1908	0.0415	0.6034	0.059*
C4	1.0431 (5)	0.0369 (4)	0.6572 (2)	0.0521 (12)
H4A	1.0784	0.0104	0.6936	0.062*
C5	0.9219 (4)	0.0579 (3)	0.6571 (2)	0.0412 (10)
C6	0.8690 (4)	0.0949 (3)	0.6038 (2)	0.0381 (10)
H6	0.7876	0.1078	0.6044	0.046*
C7	1.2442 (5)	0.1054 (5)	0.4918 (3)	0.0724 (17)
H7A	1.2804	0.1366	0.5279	0.109*
H7B	1.2748	0.1307	0.4520	0.109*
H7C	1.2625	0.0406	0.4939	0.109*
C8	0.8794 (4)	0.1474 (3)	0.48878 (19)	0.0387 (10)
H8	0.9269	0.1655	0.4540	0.046*
C9	0.6031 (4)	0.1770 (3)	0.41462 (18)	0.0348 (9)
C10	0.5622 (3)	0.1963 (3)	0.34754 (18)	0.0324 (9)
C11	0.6285 (4)	0.2436 (3)	0.30120 (19)	0.0366 (9)
H11	0.7031	0.2670	0.3123	0.044*
C12	0.5861 (4)	0.2567 (3)	0.23906 (18)	0.0400 (10)
H12	0.6320	0.2882	0.2086	0.048*
C13	0.4747 (4)	0.2226 (3)	0.22221 (19)	0.0373 (10)
C14	0.4067 (4)	0.1763 (3)	0.26778 (19)	0.0408 (10)
H14	0.3320	0.1531	0.2566	0.049*
C15	0.4499 (4)	0.1648 (3)	0.3298 (2)	0.0397 (10)
H15	0.4026	0.1351	0.3606	0.048*
H2	0.777 (4)	0.182 (4)	0.393 (2)	0.080*
C16	0.5253 (6)	0.0617 (4)	0.6017 (3)	0.0657 (15)
H16A	0.5874	0.0231	0.5844	0.099*
H16B	0.4508	0.0466	0.5811	0.099*
H16C	0.5187	0.0516	0.6476	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0692 (4)	0.1010 (5)	0.0395 (3)	−0.0096 (3)	0.0019 (2)	0.0223 (3)
N1	0.039 (2)	0.051 (2)	0.0270 (17)	−0.0015 (17)	−0.0030 (14)	0.0055 (15)
N2	0.037 (2)	0.057 (2)	0.0242 (17)	0.0008 (18)	0.0011 (14)	0.0086 (16)
O1	0.0380 (18)	0.086 (3)	0.053 (2)	0.0017 (18)	0.0135 (15)	0.0008 (18)
O2	0.0429 (17)	0.071 (2)	0.0277 (15)	−0.0026 (16)	0.0035 (13)	0.0088 (14)
O3	0.0448 (18)	0.077 (2)	0.0283 (15)	−0.0177 (17)	−0.0081 (13)	0.0087 (15)
O4	0.080 (3)	0.067 (2)	0.0300 (16)	0.007 (2)	0.0109 (16)	−0.0003 (15)
C1	0.032 (2)	0.045 (3)	0.032 (2)	−0.0008 (19)	−0.0022 (17)	−0.0001 (18)
C2	0.036 (2)	0.048 (3)	0.042 (2)	0.002 (2)	0.0020 (19)	−0.006 (2)
C3	0.033 (2)	0.057 (3)	0.056 (3)	0.005 (2)	−0.006 (2)	−0.003 (2)
C4	0.049 (3)	0.059 (3)	0.048 (3)	0.005 (2)	−0.014 (2)	0.008 (2)
C5	0.044 (3)	0.043 (3)	0.037 (2)	−0.006 (2)	−0.0039 (19)	0.0031 (19)
C6	0.031 (2)	0.048 (3)	0.035 (2)	−0.0042 (19)	−0.0032 (17)	0.0042 (19)
C7	0.040 (3)	0.086 (4)	0.091 (4)	0.002 (3)	0.022 (3)	−0.005 (4)
C8	0.037 (2)	0.049 (3)	0.030 (2)	−0.002 (2)	0.0032 (17)	0.0052 (18)
C9	0.037 (2)	0.041 (2)	0.0264 (19)	0.0014 (19)	0.0022 (16)	0.0027 (17)
C10	0.032 (2)	0.039 (2)	0.0266 (19)	0.0022 (18)	0.0013 (16)	0.0025 (16)
C11	0.032 (2)	0.049 (3)	0.029 (2)	−0.0019 (19)	−0.0015 (16)	0.0012 (19)
C12	0.036 (2)	0.058 (3)	0.026 (2)	−0.008 (2)	0.0002 (17)	0.0042 (18)
C13	0.037 (2)	0.048 (3)	0.0275 (19)	−0.0042 (19)	−0.0018 (17)	0.0002 (18)
C14	0.031 (2)	0.054 (3)	0.037 (2)	−0.007 (2)	−0.0029 (18)	0.007 (2)
C15	0.035 (2)	0.051 (3)	0.033 (2)	−0.003 (2)	0.0062 (17)	0.0095 (19)
C16	0.071 (4)	0.059 (4)	0.067 (4)	0.004 (3)	0.010 (3)	0.006 (3)

Geometric parameters (Å, º) top

Br1—C5	1.899 (4)	C5—C6	1.357 (6)
N1—C8	1.266 (6)	C6—H6	0.9300
N1—N2	1.379 (4)	C7—H7A	0.9600
N2—C9	1.354 (6)	C7—H7B	0.9600
N2—H2	0.89 (4)	C7—H7C	0.9600
O1—C2	1.362 (5)	C8—H8	0.9300
O1—C7	1.420 (6)	C9—C10	1.481 (5)
O2—C9	1.222 (5)	C10—C15	1.385 (6)
O3—C13	1.363 (5)	C10—C11	1.388 (6)
O3—H3	0.8200	C11—C12	1.378 (5)
O4—C16	1.385 (6)	C11—H11	0.9300
O4—H4	0.8200	C12—C13	1.384 (6)
C1—C6	1.386 (6)	C12—H12	0.9300
C1—C2	1.413 (6)	C13—C14	1.381 (6)
C1—C8	1.462 (6)	C14—C15	1.377 (6)
C2—C3	1.371 (6)	C14—H14	0.9300
C3—C4	1.361 (7)	C15—H15	0.9300
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.389 (7)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600

C8—N1—N2	115.9 (3)	N1—C8—C1	120.3 (4)
C9—N2—N1	118.9 (3)	N1—C8—H8	119.8
C9—N2—H2	124 (4)	C1—C8—H8	119.8
N1—N2—H2	115 (4)	O2—C9—N2	122.0 (4)
C2—O1—C7	118.6 (4)	O2—C9—C10	121.7 (4)
C13—O3—H3	109.5	N2—C9—C10	116.3 (3)
C16—O4—H4	109.5	C15—C10—C11	117.7 (4)
C6—C1—C2	118.3 (4)	C15—C10—C9	117.6 (3)
C6—C1—C8	121.9 (4)	C11—C10—C9	124.7 (4)
C2—C1—C8	119.7 (4)	C12—C11—C10	121.5 (4)
O1—C2—C3	125.5 (4)	C12—C11—H11	119.3
O1—C2—C1	114.7 (4)	C10—C11—H11	119.3
C3—C2—C1	119.8 (4)	C11—C12—C13	119.6 (4)
C4—C3—C2	121.0 (4)	C11—C12—H12	120.2
C4—C3—H3A	119.5	C13—C12—H12	120.2
C2—C3—H3A	119.5	O3—C13—C14	117.9 (4)
C3—C4—C5	119.4 (4)	O3—C13—C12	122.2 (4)
C3—C4—H4A	120.3	C14—C13—C12	119.9 (4)
C5—C4—H4A	120.3	C15—C14—C13	119.7 (4)
C6—C5—C4	120.8 (4)	C15—C14—H14	120.1
C6—C5—Br1	119.8 (3)	C13—C14—H14	120.1
C4—C5—Br1	119.4 (3)	C14—C15—C10	121.5 (4)
C5—C6—C1	120.6 (4)	C14—C15—H15	119.2
C5—C6—H6	119.7	C10—C15—H15	119.2
C1—C6—H6	119.7	O4—C16—H16A	109.5
O1—C7—H7A	109.5	O4—C16—H16B	109.5
O1—C7—H7B	109.5	H16A—C16—H16B	109.5
H7A—C7—H7B	109.5	O4—C16—H16C	109.5
O1—C7—H7C	109.5	H16A—C16—H16C	109.5
H7A—C7—H7C	109.5	H16B—C16—H16C	109.5
H7B—C7—H7C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.89 (4)	2.16 (5)	3.009 (4)	158 (5)
O4—H4···N1	0.82	2.64	3.239 (5)	131
O4—H4···O2	0.82	1.96	2.729 (4)	157
O3—H3···O4ⁱⁱ	0.82	1.78	2.602 (5)	175

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃BrN₂O₃·CH₄O
M_r	381.23
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	11.1886 (7), 14.4464 (9), 20.5927 (13)
V (Å³)	3328.5 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.49
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.598, 0.636
No. of measured, independent and observed [I > 2σ(I)] reflections	19306, 3638, 2234
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.179, 1.06
No. of reflections	3638
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)	0.95, −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···O3ⁱ	0.89 (4)	2.16 (5)	3.009 (4)	158 (5)
O4—H4···N1	0.82	2.64	3.239 (5)	131.0
O4—H4···O2	0.82	1.96	2.729 (4)	157.0
O3—H3···O4ⁱⁱ	0.82	1.78	2.602 (5)	175.1

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

Acknowledgements

We are gratefully acknowledge Chifeng University for research funding.

References

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Volume 65| Part 7| July 2009| Page o1650

doi:10.1107/S1600536809022983

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

N′-(5-Bromo-2-meth­oxy­benzyl­­idene)-4-hy­droxy­benzohydrazide methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(5-Bromo-2-methoxybenzylidene)-4-hydroxybenzohydrazide methanol solvate