(E)-N'-(4-Hydroxy-benzyl-idene)-4-hydroxy-benzohydrazide methanol solvate.

The title compound, C(14)H(12)N(2)O(3)·CH(4)O, consists of a Schiff base mol-ecule and a methanol mol-ecule of crystallization. The Schiff base mol-ecule is nearly planar, the dihedral angle between the planes of the two benzene rings being 7.2 (2)°. The mol-ecule exists in the trans configuration with respect to the methyl-idene unit. In the crystal structure, the Schiff base and methanol mol-ecules are linked through O-H⋯O, N-H⋯O and O-H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related crystal structures, see: Ban & Li (2008a ▶,b ▶); Li & Ban (2009a ▶,b ▶); Yehye et al. (2008 ▶); Fun, Patil, Jebas et al. (2008 ▶); Fun, Patil, Rao et al. (2008 ▶); Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C14H12N2O3·CH4O

M = 288.30

Monoclinic,

a = 12.927 (1) Å

b = 9.277 (1) Å

c = 11.946 (2) Å

β = 100.147 (1)°

V = 1410.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.30 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.971, T max = 0.973

8435 measured reflections

3064 independent reflections

2382 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 1.06

3064 reflections

197 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020078/wn2329sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020078/wn2329Isup2.hkl

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

C14H12N2O3·CH4O	F(000) = 608
Mr = 288.30	Dx = 1.358 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2955 reflections
a = 12.927 (1) Å	θ = 2.7–29.4°
b = 9.277 (1) Å	µ = 0.10 mm−1
c = 11.946 (2) Å	T = 298 K
β = 100.147 (1)°	Block, colorless
V = 1410.2 (3) Å3	0.30 × 0.30 × 0.28 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3064 independent reflections
Radiation source: fine-focus sealed tube	2382 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→16
Tmin = 0.971, Tmax = 0.973	k = −11→11
8435 measured reflections	l = −15→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0556P)2 + 0.2974P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3064 reflections	Δρmax = 0.22 e Å−3
197 parameters	Δρmin = −0.17 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0112 (19)

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.

	x	y	z	Uiso*/Ueq
N1	0.70137 (9)	0.02841 (13)	0.10898 (10)	0.0378 (3)
N2	0.78657 (9)	0.08908 (13)	0.07052 (10)	0.0383 (3)
O1	0.30453 (8)	−0.37263 (12)	0.13979 (9)	0.0485 (3)
H1	0.2840	−0.3402	0.1959	0.073*
O2	0.80648 (8)	0.24758 (12)	0.21426 (9)	0.0475 (3)
O3	1.21247 (9)	0.40526 (14)	0.01129 (11)	0.0588 (4)
H3	1.2348	0.4747	0.0508	0.088*
O4	0.79337 (10)	0.50038 (13)	0.33324 (9)	0.0565 (3)
H4	0.8007	0.4286	0.2953	0.085*
C1	0.56666 (10)	−0.15101 (15)	0.07692 (11)	0.0352 (3)
C2	0.52247 (11)	−0.11701 (16)	0.17196 (12)	0.0413 (4)
H2	0.5519	−0.0441	0.2208	0.050*
C3	0.43564 (11)	−0.19027 (17)	0.19437 (12)	0.0410 (3)
H3A	0.4071	−0.1669	0.2582	0.049*
C4	0.39100 (10)	−0.29833 (15)	0.12210 (11)	0.0342 (3)
C5	0.43415 (12)	−0.33417 (17)	0.02789 (13)	0.0429 (4)
H5	0.4046	−0.4072	−0.0208	0.052*
C6	0.52155 (11)	−0.26075 (17)	0.00652 (12)	0.0432 (4)
H6	0.5507	−0.2857	−0.0566	0.052*
C7	0.65706 (11)	−0.07482 (16)	0.04877 (12)	0.0392 (3)
H7	0.6834	−0.1026	−0.0156	0.047*
C8	0.83705 (10)	0.19889 (15)	0.12912 (12)	0.0347 (3)
C9	0.93302 (10)	0.25557 (14)	0.09212 (11)	0.0341 (3)
C10	0.98624 (11)	0.36828 (16)	0.15352 (13)	0.0420 (4)
H10	0.9590	0.4089	0.2133	0.050*
C11	1.07881 (12)	0.42096 (17)	0.12748 (13)	0.0443 (4)
H11	1.1135	0.4966	0.1694	0.053*
C12	1.11995 (11)	0.36095 (16)	0.03881 (13)	0.0403 (3)
C13	1.06694 (12)	0.25061 (17)	−0.02465 (13)	0.0451 (4)
H13	1.0938	0.2116	−0.0853	0.054*
C14	0.97452 (11)	0.19819 (16)	0.00163 (12)	0.0413 (4)
H14	0.9394	0.1238	−0.0414	0.050*
C15	0.74278 (19)	0.6095 (2)	0.26152 (16)	0.0737 (6)
H15A	0.7498	0.6999	0.3012	0.111*
H15B	0.6696	0.5862	0.2397	0.111*
H15C	0.7745	0.6166	0.1948	0.111*
H2A	0.8014 (16)	0.059 (2)	0.0042 (11)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0316 (6)	0.0421 (7)	0.0427 (6)	−0.0080 (5)	0.0150 (5)	0.0011 (5)
N2	0.0346 (6)	0.0438 (7)	0.0406 (7)	−0.0115 (5)	0.0174 (5)	−0.0034 (5)
O1	0.0437 (6)	0.0549 (7)	0.0533 (7)	−0.0208 (5)	0.0262 (5)	−0.0121 (5)
O2	0.0476 (6)	0.0488 (6)	0.0528 (6)	−0.0110 (5)	0.0271 (5)	−0.0127 (5)
O3	0.0459 (6)	0.0687 (8)	0.0696 (8)	−0.0257 (6)	0.0318 (6)	−0.0206 (6)
O4	0.0673 (8)	0.0592 (7)	0.0440 (6)	0.0072 (6)	0.0124 (5)	−0.0073 (5)
C1	0.0315 (7)	0.0377 (7)	0.0382 (7)	−0.0047 (6)	0.0111 (6)	0.0015 (6)
C2	0.0394 (8)	0.0447 (8)	0.0421 (8)	−0.0109 (6)	0.0135 (6)	−0.0096 (6)
C3	0.0390 (8)	0.0501 (9)	0.0379 (7)	−0.0068 (6)	0.0178 (6)	−0.0062 (6)
C4	0.0297 (7)	0.0365 (7)	0.0387 (7)	−0.0042 (5)	0.0123 (6)	0.0025 (6)
C5	0.0427 (8)	0.0450 (8)	0.0445 (8)	−0.0149 (7)	0.0170 (6)	−0.0126 (7)
C6	0.0441 (8)	0.0498 (9)	0.0405 (8)	−0.0097 (7)	0.0213 (7)	−0.0085 (7)
C7	0.0364 (7)	0.0452 (8)	0.0392 (7)	−0.0076 (6)	0.0154 (6)	−0.0015 (6)
C8	0.0319 (7)	0.0348 (7)	0.0395 (7)	−0.0012 (6)	0.0122 (6)	0.0009 (6)
C9	0.0306 (7)	0.0351 (7)	0.0382 (7)	−0.0029 (5)	0.0106 (6)	0.0015 (6)
C10	0.0396 (8)	0.0460 (8)	0.0440 (8)	−0.0073 (6)	0.0174 (6)	−0.0085 (6)
C11	0.0404 (8)	0.0463 (8)	0.0487 (9)	−0.0146 (7)	0.0144 (7)	−0.0118 (7)
C12	0.0339 (7)	0.0438 (8)	0.0462 (8)	−0.0084 (6)	0.0148 (6)	0.0001 (6)
C13	0.0423 (8)	0.0507 (9)	0.0475 (8)	−0.0093 (7)	0.0217 (7)	−0.0115 (7)
C14	0.0390 (8)	0.0413 (8)	0.0462 (8)	−0.0117 (6)	0.0146 (6)	−0.0097 (6)
C15	0.1079 (17)	0.0625 (12)	0.0508 (11)	−0.0016 (11)	0.0144 (11)	0.0044 (9)

N1—C7	1.2718 (18)	C5—C6	1.3810 (19)
N1—N2	1.3853 (15)	C5—H5	0.9300
N2—C8	1.3390 (18)	C6—H6	0.9300
N2—H2A	0.892 (9)	C7—H7	0.9300
O1—C4	1.3611 (16)	C8—C9	1.4846 (18)
O1—H1	0.8200	C9—C10	1.3881 (19)
O2—C8	1.2395 (16)	C9—C14	1.3943 (19)
O3—C12	1.3587 (16)	C10—C11	1.3780 (19)
O3—H3	0.8200	C10—H10	0.9300
O4—C15	1.410 (2)	C11—C12	1.383 (2)
O4—H4	0.8200	C11—H11	0.9300
C1—C6	1.382 (2)	C12—C13	1.382 (2)
C1—C2	1.3939 (19)	C13—C14	1.376 (2)
C1—C7	1.4549 (18)	C13—H13	0.9300
C2—C3	1.3782 (19)	C14—H14	0.9300
C2—H2	0.9300	C15—H15A	0.9600
C3—C4	1.381 (2)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600
C4—C5	1.3817 (19)
C7—N1—N2	115.06 (11)	O2—C8—N2	120.65 (12)
C8—N2—N1	118.58 (11)	O2—C8—C9	121.28 (13)
C8—N2—H2A	122.8 (14)	N2—C8—C9	118.01 (11)
N1—N2—H2A	118.4 (14)	C10—C9—C14	118.34 (12)
C4—O1—H1	109.5	C10—C9—C8	118.16 (12)
C12—O3—H3	109.5	C14—C9—C8	123.46 (12)
C15—O4—H4	109.5	C11—C10—C9	121.15 (13)
C6—C1—C2	118.21 (12)	C11—C10—H10	119.4
C6—C1—C7	119.15 (12)	C9—C10—H10	119.4
C2—C1—C7	122.64 (13)	C10—C11—C12	119.76 (14)
C3—C2—C1	120.74 (13)	C10—C11—H11	120.1
C3—C2—H2	119.6	C12—C11—H11	120.1
C1—C2—H2	119.6	O3—C12—C13	117.65 (13)
C2—C3—C4	120.09 (12)	O3—C12—C11	122.48 (13)
C2—C3—H3A	120.0	C13—C12—C11	119.87 (13)
C4—C3—H3A	120.0	C14—C13—C12	120.20 (13)
O1—C4—C3	122.32 (12)	C14—C13—H13	119.9
O1—C4—C5	117.71 (13)	C12—C13—H13	119.9
C3—C4—C5	119.97 (12)	C13—C14—C9	120.66 (13)
C6—C5—C4	119.52 (13)	C13—C14—H14	119.7
C6—C5—H5	120.2	C9—C14—H14	119.7
C4—C5—H5	120.2	O4—C15—H15A	109.5
C5—C6—C1	121.46 (13)	O4—C15—H15B	109.5
C5—C6—H6	119.3	H15A—C15—H15B	109.5
C1—C6—H6	119.3	O4—C15—H15C	109.5
N1—C7—C1	122.36 (13)	H15A—C15—H15C	109.5
N1—C7—H7	118.8	H15B—C15—H15C	109.5
C1—C7—H7	118.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.90	2.6877 (14)	160
O1—H1···N1i	0.82	2.61	3.1521 (16)	125
O3—H3···O1ii	0.82	1.90	2.7156 (15)	172
O4—H4···O2	0.82	1.95	2.7629 (15)	173
N2—H2A···O4iii	0.89 (1)	2.10 (1)	2.9695 (16)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.90	2.6877 (14)	160
O1—H1⋯N1i	0.82	2.61	3.1521 (16)	125
O3—H3⋯O1ii	0.82	1.90	2.7156 (15)	172
O4—H4⋯O2	0.82	1.95	2.7629 (15)	173
N2—H2A⋯O4iii	0.892 (9)	2.100 (11)	2.9695 (16)	164.6 (19)

Symmetry codes: (i) ; (ii) ; (iii) .