(E)-N′-(3,4-Dimethoxy­benzyl­idene)-2,4-dihydroxy­benzohydrazide methanol solvate

Zhang, Q.-L.; Yin, L.-Z.; Deng, X.-M.; Liu, S.-C.; Song, D.-G.

doi:10.1107/S1600536809035752

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2392-o2393

doi:10.1107/S1600536809035752

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(E)-N′-(3,4-Dimethoxybenzylidene)-2,4-dihydroxybenzohydrazide methanol solvate

Qiao-Ling Zhang,^a Li-Zi Yin,^a Xu-Ming Deng,^a Song-Cai Liu ^a ^* and De-Guang Song ^a ^*

^aCollege of Animal Science and Veterinary Medicine, Jilin University, Changchun 130062, People's Republic of China
^*Correspondence e-mail: liusongcai09@163.com,

(Received 2 September 2009; accepted 4 September 2009; online 9 September 2009)

The title compound, C₁₆H₁₆N₂O₅·CH₃OH, was obtained from a condensation reaction of 3,4-dimethoxybenzaldehyde and 2,4-dihydroxybenzohydrazide. The non-H atoms of the Schiff base molecule are approximately coplanar (r.m.s. deviation = 0.043 Å) and the dihedral angle between the two benzene rings is 1.6 (1)°. The molecule adopts an E configuration with respect to the C=N double bond. An intramolecular O—H⋯O hydrogen bond is observed. The Schiff base and methanol molecules are linked into a two-dimensional network parallel to (10 $[\overline{1}]$ ) by intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds.

Related literature

For background to Schiff base compounds, hydrazone compounds and their biological properties, see: Kucukguzel et al. (2006 ); Khattab et al. (2005 ); Karthikeyan et al. (2006 ); Okabe et al. (1993 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see: Shan et al. (2008 ); Fun et al. (2008 ); Ma et al. (2008 ); Diao et al. (2008a ,b ); Ejsmont et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₅·CH₄O
M_r = 348.35
Monoclinic, P 2₁ /n
a = 8.497 (1) Å
b = 17.431 (2) Å
c = 11.933 (2) Å
β = 102.93 (2)°
V = 1722.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.25 × 0.23 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.975, T_max = 0.977
10465 measured reflections
3732 independent reflections
2017 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.129
S = 1.03
3732 reflections
235 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.90 (1)	2.217 (10)	3.108 (2)	170 (2)
O6—H6⋯N2ⁱⁱ	0.82	2.55	3.133 (2)	129
O6—H6⋯O3ⁱⁱ	0.82	2.02	2.807 (2)	161
O2—H2⋯O6ⁱⁱⁱ	0.82	1.79	2.599 (2)	171
O1—H1⋯O3	0.82	1.80	2.534 (2)	148
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x+1, y, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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 global, I. DOI: 10.1107/S1600536809035752/ci2900sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035752/ci2900Isup2.hkl

checkCIF report

Comment top

Hydrazones and Schiff bases have been attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab et al., 2005; Karthikeyan et al., 2006; Okabe et al., 1993). Recently, a large number of hydrazone derivatives have been prepared and structurally characterized (Shan et al., 2008; Fun et al., 2008; Ma et al., 2008; Diao et al., 2008a,b; Ejsmont et al., 2008). As part of the ongoing study, we report herein the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The compound consists of a Schiff base molecule and a methanol molecule. The dihedral angle between the two benzene rings is 1.6 (1)°. The Schiff base molecule displays an E configuration about the C═N bond. The bond lengths are typical (Allen et al., 1987). The molecules are linked into a two-dimensional network parallel to the (101) by intermolecular N—H···O, O—H···N, and O—H···O hydrogen bonds (Fig. 2 and Table 1).

Related literature top

For background to Schiff base compounds, hydrazone compounds and their biological properties, see: Kucukguzel et al. (2006); Khattab et al. (2005); Karthikeyan et al. (2006); Okabe et al. (1993). For bond-length data, see: Allen et al. (1987). For related structures, see: Shan et al. (2008); Fun et al. (2008); Ma et al. (2008); Diao et al. (2008a,b); Ejsmont et al. (2008).

Experimental top

3,4-Dimethoxybenzaldehyde (1.0 mmol, 166.2 mg) was dissolved in methanol (50 ml), then 2,4-dihydroxybenzohydrazide (1.0 mmol, 168.2 mg) was added slowly into the solution, and the mixture was kept at reflux with continuous stirring for 1 h. After the solution had cooled to room temperature colourless crystallites appeared. The crystallites were filtered and washed with methanol for three times. Recrystallization from an absolute methanol yielded block-shaped single crystals of the title compound.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. The dashed line indicates an intramolecular hydrogen bond.
	Fig. 2. The molecular packing of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

(E)-N'-(3,4-Dimethoxybenzylidene)-2,4-dihydroxybenzohydrazide methanol solvate top

Crystal data top

C₁₆H₁₆N₂O₅·CH₄O	F(000) = 736
M_r = 348.35	D_x = 1.343 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1327 reflections
a = 8.497 (1) Å	θ = 2.3–24.5°
b = 17.431 (2) Å	µ = 0.10 mm⁻¹
c = 11.933 (2) Å	T = 298 K
β = 102.93 (2)°	Block, colourless
V = 1722.6 (4) Å³	0.25 × 0.23 × 0.23 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3732 independent reflections
Radiation source: fine-focus sealed tube	2017 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.975, T_max = 0.977	k = −20→22
10465 measured reflections	l = −15→7

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0522P)² + 0.0211P] where P = (F_o² + 2F_c²)/3
3732 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₅·CH₄O	V = 1722.6 (4) Å³
M_r = 348.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.497 (1) Å	µ = 0.10 mm⁻¹
b = 17.431 (2) Å	T = 298 K
c = 11.933 (2) Å	0.25 × 0.23 × 0.23 mm
β = 102.93 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3732 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2017 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.977	R_int = 0.043
10465 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	1 restraint
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.15 e Å⁻³
3732 reflections	Δρ_min = −0.19 e Å⁻³
235 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
N1	0.9655 (2)	0.08862 (10)	0.61461 (15)	0.0408 (4)
N2	0.8536 (2)	0.03538 (10)	0.56016 (14)	0.0414 (4)
O1	1.2219 (2)	0.05972 (9)	0.95309 (12)	0.0623 (5)
H1	1.1561	0.0316	0.9118	0.093*
O2	1.52034 (18)	0.28449 (9)	0.94432 (11)	0.0499 (4)
H2	1.5442	0.3149	0.8984	0.075*
O3	1.01873 (19)	0.01674 (9)	0.77490 (12)	0.0544 (4)
O4	0.42243 (18)	−0.17176 (9)	0.40757 (13)	0.0562 (4)
O5	0.29676 (18)	−0.13286 (8)	0.19882 (13)	0.0582 (5)
O6	0.6296 (2)	0.37824 (9)	0.81028 (13)	0.0639 (5)
H6	0.5949	0.4222	0.8007	0.096*
C1	1.1618 (2)	0.13446 (11)	0.77945 (16)	0.0379 (5)
C2	1.2479 (3)	0.12222 (12)	0.89285 (17)	0.0419 (5)
C3	1.3640 (3)	0.17364 (13)	0.94638 (17)	0.0445 (5)
H3	1.4178	0.1655	1.0223	0.053*
C4	1.4008 (2)	0.23680 (12)	0.88820 (17)	0.0393 (5)
C5	1.3173 (3)	0.25089 (12)	0.77654 (17)	0.0461 (6)
H5	1.3401	0.2942	0.7375	0.055*
C6	1.2005 (2)	0.20011 (12)	0.72414 (17)	0.0442 (6)
H6A	1.1450	0.2098	0.6490	0.053*
C7	1.0444 (2)	0.07663 (12)	0.72359 (17)	0.0401 (5)
C8	0.7848 (2)	0.05124 (12)	0.45725 (18)	0.0412 (5)
H8	0.8152	0.0956	0.4242	0.049*
C9	0.6598 (2)	0.00287 (11)	0.38858 (17)	0.0373 (5)
C10	0.6063 (2)	−0.06345 (11)	0.43485 (17)	0.0408 (5)
H10	0.6532	−0.0781	0.5098	0.049*
C11	0.4845 (2)	−0.10693 (11)	0.36970 (18)	0.0414 (5)
C12	0.4150 (2)	−0.08531 (12)	0.25628 (18)	0.0434 (5)
C13	0.4679 (3)	−0.02028 (12)	0.21043 (18)	0.0479 (6)
H13	0.4218	−0.0057	0.1353	0.057*
C14	0.5908 (3)	0.02357 (12)	0.27733 (17)	0.0443 (5)
H14	0.6267	0.0674	0.2463	0.053*
C15	0.4975 (3)	−0.19856 (14)	0.5184 (2)	0.0648 (7)
H15A	0.6088	−0.2100	0.5209	0.097*
H15B	0.4437	−0.2441	0.5353	0.097*
H15C	0.4912	−0.1597	0.5743	0.097*
C16	0.2220 (3)	−0.11211 (15)	0.0836 (2)	0.0661 (7)
H16A	0.1795	−0.0610	0.0826	0.099*
H16B	0.1358	−0.1473	0.0539	0.099*
H16C	0.3004	−0.1141	0.0369	0.099*
C17	0.6766 (4)	0.35311 (16)	0.7103 (2)	0.0814 (9)
H17A	0.7812	0.3736	0.7093	0.122*
H17B	0.5995	0.3705	0.6436	0.122*
H17C	0.6812	0.2981	0.7099	0.122*
H1A	0.979 (2)	0.1297 (8)	0.5719 (15)	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0420 (10)	0.0382 (11)	0.0393 (11)	−0.0067 (9)	0.0028 (8)	−0.0003 (8)
N2	0.0418 (10)	0.0372 (11)	0.0433 (11)	−0.0048 (8)	0.0056 (8)	−0.0044 (8)
O1	0.0787 (13)	0.0582 (11)	0.0429 (10)	−0.0152 (9)	−0.0014 (8)	0.0154 (8)
O2	0.0562 (10)	0.0511 (10)	0.0370 (9)	−0.0089 (8)	−0.0011 (7)	−0.0071 (7)
O3	0.0647 (11)	0.0474 (10)	0.0475 (10)	−0.0106 (8)	0.0049 (8)	0.0089 (7)
O4	0.0589 (10)	0.0405 (9)	0.0654 (11)	−0.0096 (8)	0.0057 (8)	0.0064 (8)
O5	0.0585 (10)	0.0475 (10)	0.0598 (11)	−0.0110 (8)	−0.0056 (8)	−0.0038 (8)
O6	0.0943 (14)	0.0413 (10)	0.0577 (11)	−0.0014 (10)	0.0201 (9)	−0.0022 (8)
C1	0.0427 (12)	0.0373 (12)	0.0311 (12)	0.0030 (10)	0.0031 (9)	0.0000 (9)
C2	0.0522 (13)	0.0417 (13)	0.0321 (12)	0.0043 (11)	0.0099 (10)	0.0038 (10)
C3	0.0528 (13)	0.0486 (14)	0.0286 (12)	0.0043 (11)	0.0012 (10)	−0.0003 (10)
C4	0.0408 (12)	0.0401 (13)	0.0340 (12)	0.0023 (10)	0.0023 (9)	−0.0099 (10)
C5	0.0559 (14)	0.0419 (14)	0.0354 (13)	−0.0025 (11)	−0.0005 (10)	0.0033 (10)
C6	0.0521 (13)	0.0445 (14)	0.0297 (12)	−0.0002 (11)	−0.0043 (10)	0.0016 (10)
C7	0.0419 (12)	0.0399 (13)	0.0367 (13)	0.0026 (10)	0.0048 (10)	0.0000 (10)
C8	0.0415 (12)	0.0352 (12)	0.0453 (14)	−0.0023 (10)	0.0063 (10)	−0.0015 (10)
C9	0.0368 (12)	0.0316 (12)	0.0419 (13)	−0.0005 (9)	0.0053 (9)	−0.0040 (9)
C10	0.0418 (12)	0.0368 (13)	0.0416 (13)	0.0029 (10)	0.0047 (10)	−0.0026 (10)
C11	0.0424 (12)	0.0294 (12)	0.0530 (14)	0.0006 (10)	0.0116 (10)	−0.0015 (10)
C12	0.0414 (12)	0.0339 (12)	0.0513 (15)	−0.0027 (10)	0.0026 (10)	−0.0103 (10)
C13	0.0506 (14)	0.0445 (14)	0.0446 (14)	−0.0028 (11)	0.0022 (11)	−0.0019 (11)
C14	0.0482 (13)	0.0377 (13)	0.0449 (14)	−0.0052 (10)	0.0059 (10)	0.0011 (10)
C15	0.0699 (17)	0.0456 (15)	0.0781 (19)	−0.0015 (13)	0.0147 (14)	0.0184 (13)
C16	0.0569 (15)	0.0674 (18)	0.0628 (18)	−0.0137 (14)	−0.0104 (12)	−0.0078 (13)
C17	0.114 (3)	0.072 (2)	0.0633 (19)	−0.0190 (18)	0.0304 (17)	−0.0166 (15)

Geometric parameters (Å, º) top

N1—C7	1.339 (3)	C5—H5	0.93
N1—N2	1.382 (2)	C6—H6A	0.93
N1—H1A	0.901 (9)	C8—C9	1.456 (3)
N2—C8	1.267 (2)	C8—H8	0.93
O1—C2	1.350 (2)	C9—C14	1.374 (3)
O1—H1	0.82	C9—C10	1.400 (3)
O2—C4	1.367 (2)	C10—C11	1.375 (3)
O2—H2	0.82	C10—H10	0.93
O3—C7	1.254 (2)	C11—C12	1.402 (3)
O4—C11	1.366 (2)	C12—C13	1.377 (3)
O4—C15	1.413 (3)	C13—C14	1.393 (3)
O5—C12	1.363 (2)	C13—H13	0.93
O5—C16	1.426 (3)	C14—H14	0.93
O6—C17	1.410 (3)	C15—H15A	0.96
O6—H6	0.82	C15—H15B	0.96
C1—C6	1.397 (3)	C15—H15C	0.96
C1—C2	1.403 (3)	C16—H16A	0.96
C1—C7	1.469 (3)	C16—H16B	0.96
C2—C3	1.380 (3)	C16—H16C	0.96
C3—C4	1.374 (3)	C17—H17A	0.96
C3—H3	0.93	C17—H17B	0.96
C4—C5	1.384 (3)	C17—H17C	0.96
C5—C6	1.372 (3)

C7—N1—N2	119.58 (17)	C10—C9—C8	121.09 (19)
C7—N1—H1A	125.0 (14)	C11—C10—C9	120.1 (2)
N2—N1—H1A	115.4 (13)	C11—C10—H10	119.9
C8—N2—N1	115.41 (17)	C9—C10—H10	119.9
C2—O1—H1	109.5	O4—C11—C10	124.5 (2)
C4—O2—H2	109.5	O4—C11—C12	115.55 (18)
C11—O4—C15	117.13 (17)	C10—C11—C12	119.9 (2)
C12—O5—C16	116.74 (18)	O5—C12—C13	124.7 (2)
C17—O6—H6	109.5	O5—C12—C11	115.22 (19)
C6—C1—C2	116.94 (18)	C13—C12—C11	120.03 (19)
C6—C1—C7	123.76 (18)	C12—C13—C14	119.6 (2)
C2—C1—C7	119.21 (18)	C12—C13—H13	120.2
O1—C2—C3	117.58 (19)	C14—C13—H13	120.2
O1—C2—C1	121.59 (19)	C9—C14—C13	120.9 (2)
C3—C2—C1	120.83 (19)	C9—C14—H14	119.6
C4—C3—C2	120.42 (19)	C13—C14—H14	119.6
C4—C3—H3	119.8	O4—C15—H15A	109.5
C2—C3—H3	119.8	O4—C15—H15B	109.5
O2—C4—C3	117.89 (18)	H15A—C15—H15B	109.5
O2—C4—C5	121.9 (2)	O4—C15—H15C	109.5
C3—C4—C5	120.2 (2)	H15A—C15—H15C	109.5
C6—C5—C4	119.1 (2)	H15B—C15—H15C	109.5
C6—C5—H5	120.4	O5—C16—H16A	109.5
C4—C5—H5	120.4	O5—C16—H16B	109.5
C5—C6—C1	122.43 (19)	H16A—C16—H16B	109.5
C5—C6—H6A	118.8	O5—C16—H16C	109.5
C1—C6—H6A	118.8	H16A—C16—H16C	109.5
O3—C7—N1	120.01 (19)	H16B—C16—H16C	109.5
O3—C7—C1	121.63 (19)	O6—C17—H17A	109.5
N1—C7—C1	118.35 (19)	O6—C17—H17B	109.5
N2—C8—C9	122.7 (2)	H17A—C17—H17B	109.5
N2—C8—H8	118.7	O6—C17—H17C	109.5
C9—C8—H8	118.7	H17A—C17—H17C	109.5
C14—C9—C10	119.45 (18)	H17B—C17—H17C	109.5
C14—C9—C8	119.44 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.90 (1)	2.22 (1)	3.108 (2)	170 (2)
O6—H6···N2ⁱⁱ	0.82	2.55	3.133 (2)	129
O6—H6···O3ⁱⁱ	0.82	2.02	2.807 (2)	161
O2—H2···O6ⁱⁱⁱ	0.82	1.79	2.599 (2)	171
O1—H1···O3	0.82	1.80	2.534 (2)	148

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₅·CH₄O
M_r	348.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.497 (1), 17.431 (2), 11.933 (2)
β (°)	102.93 (2)
V (Å³)	1722.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.23 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.975, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	10465, 3732, 2017
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.129, 1.03
No. of reflections	3732
No. of parameters	235
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)	0.15, −0.19

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.90 (1)	2.217 (10)	3.108 (2)	170 (2)
O6—H6···N2ⁱⁱ	0.82	2.55	3.133 (2)	129
O6—H6···O3ⁱⁱ	0.82	2.02	2.807 (2)	161
O2—H2···O6ⁱⁱⁱ	0.82	1.79	2.599 (2)	171
O1—H1···O3	0.82	1.80	2.534 (2)	148

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2392-o2393

doi:10.1107/S1600536809035752

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

(E)-N′-(3,4-Di­meth­oxy­benzyl­­idene)-2,4-di­hydroxy­benzohydrazide methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(E)-N′-(3,4-Dimethoxybenzylidene)-2,4-dihydroxybenzohydrazide methanol solvate