(E)-N'-(3,4-Dimethoxy-benzyl-idene)-2,4-dihydroxy-benzohydrazide methanol solvate.

The title compound, C(16)H(16)N(2)O(5)·CH(3)OH, was obtained from a condensation reaction of 3,4-dimethoxy-benzaldehyde and 2,4-dihydroxy-benzohydrazide. The non-H atoms of the Schiff base mol-ecule are approximately coplanar (r.m.s. deviation = 0.043 Å) and the dihedral angle between the two benzene rings is 1.6 (1)°. The mol-ecule adopts an E configuration with respect to the C=N double bond. An intra-molecular O-H⋯O hydrogen bond is observed. The Schiff base and methanol mol-ecules are linked into a two-dimensional network parallel to (10) by inter-molecular 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 = 348.35

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.129

S = 1.03

3732 reflections

235 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035752/ci2900sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H16N2O5·CH4O	F(000) = 736
Mr = 348.35	Dx = 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

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

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 = 1.02	w = 1/[σ2(Fo2) + (0.0522P)2 + 0.0211P] where P = (Fo2 + 2Fc2)/3
3732 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .