(E)-4-Meth-oxy-N'-(3,4,5-trihy-droxy-benzyl-idene)benzohydrazide methanol monosolvate.

The title compound, C(15)H(14)N(2)O(5)·CH(3)OH, displays an E conformation about the azomethine double bond [C=N = 1.277 (2) Å] and the benzene rings are inclined to one another by 18.28 (9)°. An intra-molecular O-H⋯O hydrogen bond occurs between the para-OH group and one of the meta-O atoms of the 3,4,5-trihy-droxy-benzyl-idene group. In the crystal, the components are linked into a three dimensional network by O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds.

Related literature

For the biological activity of benzohydrazides see: Khan et al. (2012 ▶). For a related structure, see: Bao & Wei (2008 ▶).

Experimental

Crystal data

C15H14N2O5·CH4O

M = 334.32

Monoclinic,

a = 11.1846 (7) Å

b = 11.1909 (7) Å

c = 13.1806 (8) Å

β = 110.368 (1)°

V = 1546.61 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.20 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.978, T max = 0.991

8994 measured reflections

2787 independent reflections

2230 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.03

2787 reflections

239 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036550/hb6938sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036550/hb6938Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036550/hb6938Isup3.cml

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

C15H14N2O5·CH4O	F(000) = 704
Mr = 334.32	Dx = 1.436 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.1846 (7) Å	Cell parameters from 506 reflections
b = 11.1909 (7) Å	θ = 2.9–18.7°
c = 13.1806 (8) Å	µ = 0.11 mm−1
β = 110.368 (1)°	T = 298 K
V = 1546.61 (17) Å3	Plate, colourless
Z = 4	0.20 × 0.14 × 0.08 mm

Bruker SMART APEX CCD diffractometer	2787 independent reflections
Radiation source: fine-focus sealed tube	2230 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scan	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
Tmin = 0.978, Tmax = 0.991	k = −13→13
8994 measured reflections	l = −15→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.3148P] where P = (Fo2 + 2Fc2)/3
2787 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.23 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
O1	0.01454 (13)	0.88419 (13)	−0.45071 (12)	0.0441 (4)
O2	−0.21003 (12)	0.80276 (13)	−0.45786 (12)	0.0444 (4)
O3	−0.23582 (12)	0.64930 (13)	−0.31207 (12)	0.0433 (4)
O4	0.27016 (11)	0.46606 (12)	0.13725 (10)	0.0392 (4)
O5	0.84976 (13)	0.48797 (14)	0.44630 (12)	0.0565 (5)
N1	0.23081 (13)	0.59842 (13)	−0.03975 (12)	0.0316 (4)
N2	0.35158 (14)	0.57371 (14)	0.03333 (13)	0.0324 (4)
C1	−0.00733 (16)	0.64529 (15)	−0.21803 (15)	0.0310 (4)
H1C	−0.0151	0.5926	−0.1661	0.037*
C2	−0.11475 (15)	0.68460 (15)	−0.30027 (15)	0.0302 (4)
C3	−0.10337 (15)	0.76480 (15)	−0.37722 (15)	0.0303 (4)
C4	0.01662 (17)	0.80498 (15)	−0.37121 (15)	0.0309 (4)
C5	0.12434 (16)	0.76476 (16)	−0.29044 (15)	0.0334 (4)
H5A	0.2045	0.7907	−0.2875	0.040*
C6	0.11294 (15)	0.68481 (15)	−0.21292 (14)	0.0297 (4)
C7	0.22964 (16)	0.64711 (16)	−0.12773 (15)	0.0319 (4)
H7A	0.3070	0.6591	−0.1379	0.038*
C8	0.36450 (15)	0.51158 (14)	0.12353 (14)	0.0285 (4)
C9	0.49511 (16)	0.50096 (15)	0.20356 (14)	0.0298 (4)
C10	0.52163 (17)	0.41047 (16)	0.28054 (16)	0.0351 (4)
H10A	0.4584	0.3553	0.2779	0.042*
C11	0.63947 (17)	0.40068 (17)	0.36061 (16)	0.0383 (5)
H11A	0.6558	0.3382	0.4101	0.046*
C12	0.73406 (17)	0.48409 (17)	0.36761 (16)	0.0395 (5)
C13	0.71055 (18)	0.57266 (18)	0.28968 (17)	0.0449 (5)
H13A	0.7745	0.6267	0.2919	0.054*
C14	0.59328 (17)	0.58108 (16)	0.20925 (16)	0.0385 (5)
H14A	0.5788	0.6411	0.1576	0.046*
C15	0.8744 (2)	0.4109 (2)	0.53777 (18)	0.0556 (6)
H15A	0.9566	0.4291	0.5901	0.083*
H15B	0.8731	0.3292	0.5150	0.083*
H15C	0.8100	0.4225	0.5696	0.083*
O6	0.47061 (15)	0.26843 (15)	0.01508 (15)	0.0603 (5)
C16	0.4983 (3)	0.1595 (2)	0.0630 (2)	0.0762 (8)
H16A	0.5879	0.1439	0.0822	0.114*
H16B	0.4507	0.0991	0.0136	0.114*
H16C	0.4759	0.1583	0.1270	0.114*
H2B	0.4110 (19)	0.6045 (17)	0.0225 (16)	0.034 (5)*
H2A	−0.190 (2)	0.846 (2)	−0.496 (2)	0.058 (8)*
H1A	0.083 (2)	0.897 (2)	−0.448 (2)	0.057 (8)*
H3A	−0.238 (2)	0.609 (2)	−0.257 (2)	0.059 (7)*
H6A	0.384 (3)	0.274 (3)	−0.010 (2)	0.093 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0267 (7)	0.0576 (9)	0.0482 (10)	0.0040 (6)	0.0133 (7)	0.0264 (7)
O2	0.0245 (7)	0.0606 (9)	0.0436 (9)	0.0040 (6)	0.0062 (6)	0.0261 (7)
O3	0.0233 (7)	0.0627 (9)	0.0404 (9)	−0.0039 (6)	0.0067 (6)	0.0198 (7)
O4	0.0273 (7)	0.0557 (8)	0.0321 (8)	−0.0078 (6)	0.0073 (6)	0.0068 (6)
O5	0.0318 (7)	0.0713 (10)	0.0498 (10)	−0.0093 (7)	−0.0066 (7)	0.0251 (8)
N1	0.0213 (7)	0.0384 (8)	0.0298 (9)	0.0029 (6)	0.0024 (7)	0.0042 (7)
N2	0.0179 (7)	0.0440 (9)	0.0319 (9)	−0.0009 (6)	0.0045 (7)	0.0084 (7)
C1	0.0292 (9)	0.0379 (9)	0.0239 (10)	0.0006 (7)	0.0066 (8)	0.0051 (7)
C2	0.0221 (8)	0.0372 (9)	0.0305 (11)	−0.0005 (7)	0.0082 (8)	0.0019 (8)
C3	0.0226 (8)	0.0376 (9)	0.0283 (10)	0.0052 (7)	0.0059 (8)	0.0058 (8)
C4	0.0301 (9)	0.0340 (9)	0.0307 (10)	0.0025 (7)	0.0131 (8)	0.0072 (8)
C5	0.0213 (8)	0.0413 (10)	0.0367 (11)	0.0002 (7)	0.0090 (8)	0.0054 (8)
C6	0.0245 (9)	0.0354 (9)	0.0266 (10)	0.0026 (7)	0.0054 (8)	0.0005 (7)
C7	0.0231 (9)	0.0403 (9)	0.0310 (11)	0.0000 (7)	0.0077 (8)	0.0021 (8)
C8	0.0257 (9)	0.0309 (8)	0.0281 (10)	−0.0005 (7)	0.0084 (8)	−0.0019 (7)
C9	0.0269 (9)	0.0331 (9)	0.0269 (10)	0.0007 (7)	0.0064 (8)	0.0004 (7)
C10	0.0290 (9)	0.0371 (9)	0.0372 (12)	−0.0044 (7)	0.0091 (9)	0.0045 (8)
C11	0.0340 (10)	0.0402 (10)	0.0365 (12)	0.0021 (8)	0.0069 (9)	0.0127 (8)
C12	0.0264 (9)	0.0493 (11)	0.0361 (12)	0.0001 (8)	0.0024 (9)	0.0078 (9)
C13	0.0303 (10)	0.0509 (11)	0.0460 (13)	−0.0109 (8)	0.0037 (9)	0.0118 (10)
C14	0.0338 (10)	0.0419 (10)	0.0340 (12)	−0.0040 (8)	0.0046 (9)	0.0112 (8)
C15	0.0387 (12)	0.0720 (15)	0.0424 (14)	−0.0027 (10)	−0.0030 (10)	0.0214 (11)
O6	0.0305 (8)	0.0738 (11)	0.0694 (12)	−0.0075 (7)	0.0084 (8)	0.0217 (9)
C16	0.0721 (18)	0.0712 (17)	0.091 (2)	−0.0080 (14)	0.0349 (17)	0.0196 (16)

O1—C4	1.366 (2)	C6—C7	1.457 (2)
O1—H1A	0.77 (3)	C7—H7A	0.9300
O2—C3	1.360 (2)	C8—C9	1.479 (2)
O2—H2A	0.78 (3)	C9—C10	1.391 (2)
O3—C2	1.366 (2)	C9—C14	1.399 (2)
O3—H3A	0.86 (3)	C10—C11	1.376 (3)
O4—C8	1.240 (2)	C10—H10A	0.9300
O5—C12	1.348 (2)	C11—C12	1.390 (3)
O5—C15	1.429 (2)	C11—H11A	0.9300
N1—C7	1.277 (2)	C12—C13	1.385 (3)
N1—N2	1.3867 (19)	C13—C14	1.373 (3)
N2—C8	1.341 (2)	C13—H13A	0.9300
N2—H2B	0.80 (2)	C14—H14A	0.9300
C1—C2	1.380 (2)	C15—H15A	0.9600
C1—C6	1.395 (2)	C15—H15B	0.9600
C1—H1C	0.9300	C15—H15C	0.9600
C2—C3	1.393 (2)	O6—C16	1.358 (3)
C3—C4	1.391 (2)	O6—H6A	0.91 (3)
C4—C5	1.376 (2)	C16—H16A	0.9600
C5—C6	1.397 (3)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C4—O1—H1A	109.2 (18)	C10—C9—C14	117.61 (16)
C3—O2—H2A	108.8 (18)	C10—C9—C8	119.06 (15)
C2—O3—H3A	111.6 (16)	C14—C9—C8	123.27 (16)
C12—O5—C15	118.75 (15)	C11—C10—C9	121.43 (16)
C7—N1—N2	114.55 (14)	C11—C10—H10A	119.3
C8—N2—N1	119.84 (15)	C9—C10—H10A	119.3
C8—N2—H2B	122.6 (14)	C10—C11—C12	120.08 (17)
N1—N2—H2B	117.2 (14)	C10—C11—H11A	120.0
C2—C1—C6	119.86 (16)	C12—C11—H11A	120.0
C2—C1—H1C	120.1	O5—C12—C13	115.53 (16)
C6—C1—H1C	120.1	O5—C12—C11	125.27 (17)
O3—C2—C1	123.67 (16)	C13—C12—C11	119.19 (17)
O3—C2—C3	116.20 (15)	C14—C13—C12	120.36 (17)
C1—C2—C3	120.13 (15)	C14—C13—H13A	119.8
O2—C3—C4	120.65 (16)	C12—C13—H13A	119.8
O2—C3—C2	119.50 (15)	C13—C14—C9	121.22 (17)
C4—C3—C2	119.84 (16)	C13—C14—H14A	119.4
O1—C4—C5	125.59 (16)	C9—C14—H14A	119.4
O1—C4—C3	114.04 (16)	O5—C15—H15A	109.5
C5—C4—C3	120.37 (16)	O5—C15—H15B	109.5
C4—C5—C6	119.81 (16)	H15A—C15—H15B	109.5
C4—C5—H5A	120.1	O5—C15—H15C	109.5
C6—C5—H5A	120.1	H15A—C15—H15C	109.5
C1—C6—C5	119.98 (16)	H15B—C15—H15C	109.5
C1—C6—C7	122.38 (16)	C16—O6—H6A	106.1 (19)
C5—C6—C7	117.64 (15)	O6—C16—H16A	109.5
N1—C7—C6	123.15 (16)	O6—C16—H16B	109.5
N1—C7—H7A	118.4	H16A—C16—H16B	109.5
C6—C7—H7A	118.4	O6—C16—H16C	109.5
O4—C8—N2	120.50 (16)	H16A—C16—H16C	109.5
O4—C8—C9	122.83 (16)	H16B—C16—H16C	109.5
N2—C8—C9	116.67 (15)
C7—N1—N2—C8	−173.13 (16)	C5—C6—C7—N1	162.91 (17)
C6—C1—C2—O3	179.17 (17)	N1—N2—C8—O4	7.0 (3)
C6—C1—C2—C3	−0.9 (3)	N1—N2—C8—C9	−173.02 (15)
O3—C2—C3—O2	−0.1 (3)	O4—C8—C9—C10	19.5 (3)
C1—C2—C3—O2	179.97 (16)	N2—C8—C9—C10	−160.50 (16)
O3—C2—C3—C4	−179.83 (17)	O4—C8—C9—C14	−157.59 (18)
C1—C2—C3—C4	0.2 (3)	N2—C8—C9—C14	22.5 (3)
O2—C3—C4—O1	0.9 (3)	C14—C9—C10—C11	0.9 (3)
C2—C3—C4—O1	−179.34 (16)	C8—C9—C10—C11	−176.26 (17)
O2—C3—C4—C5	−178.95 (17)	C9—C10—C11—C12	1.7 (3)
C2—C3—C4—C5	0.8 (3)	C15—O5—C12—C13	171.0 (2)
O1—C4—C5—C6	179.03 (17)	C15—O5—C12—C11	−8.2 (3)
C3—C4—C5—C6	−1.2 (3)	C10—C11—C12—O5	175.53 (19)
C2—C1—C6—C5	0.5 (3)	C10—C11—C12—C13	−3.6 (3)
C2—C1—C6—C7	179.59 (16)	O5—C12—C13—C14	−176.38 (19)
C4—C5—C6—C1	0.5 (3)	C11—C12—C13—C14	2.8 (3)
C4—C5—C6—C7	−178.63 (16)	C12—C13—C14—C9	−0.2 (3)
N2—N1—C7—C6	−177.28 (15)	C10—C9—C14—C13	−1.7 (3)
C1—C6—C7—N1	−16.2 (3)	C8—C9—C14—C13	175.34 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4i	0.77 (3)	2.52 (2)	3.165 (2)	142 (2)
O1—H1A···N1i	0.77 (2)	2.36 (3)	3.040 (2)	147 (2)
O2—H2A···O1	0.79 (2)	2.20 (2)	2.643 (2)	117 (2)
O2—H2A···O4ii	0.79 (2)	2.22 (2)	2.877 (2)	142 (2)
O3—H3A···O4iii	0.86 (2)	1.93 (2)	2.782 (2)	170 (2)
O6—H6A···O2iv	0.91 (3)	1.87 (3)	2.771 (2)	171 (2)
N2—H2B···O6v	0.80 (2)	2.12 (2)	2.893 (2)	162 (2)
C7—H7A···O6v	0.93	2.58	3.297 (3)	134
C14—H14A···O6v	0.93	2.37	3.259 (3)	159
C15—H15A···O5vi	0.96	2.55	3.224 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4i	0.77 (3)	2.52 (2)	3.165 (2)	142 (2)
O1—H1A⋯N1i	0.77 (2)	2.36 (3)	3.040 (2)	147 (2)
O2—H2A⋯O1	0.79 (2)	2.20 (2)	2.643 (2)	117 (2)
O2—H2A⋯O4ii	0.79 (2)	2.22 (2)	2.877 (2)	142 (2)
O3—H3A⋯O4iii	0.86 (2)	1.93 (2)	2.782 (2)	170 (2)
O6—H6A⋯O2iv	0.91 (3)	1.87 (3)	2.771 (2)	171 (2)
N2—H2B⋯O6v	0.80 (2)	2.12 (2)	2.893 (2)	162 (2)
C7—H7A⋯O6v	0.93	2.58	3.297 (3)	134
C14—H14A⋯O6v	0.93	2.37	3.259 (3)	159
C15—H15A⋯O5vi	0.96	2.55	3.224 (3)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .