2-Hy-droxy-N'-(4-hy-droxy-benzyl-idene)-3-methyl-benzohydrazide.

The title compound, C(15)H(14)N(2)O(3), was prepared by condensing 4-hy-droxy-benzaldehyde and 2-hy-droxy-3-methyl-benzo-hydra-zide in methanol. The two benzene rings make a dihedral angle of 19.03 (11)°. An intra-molecular O-H⋯O hydrogen bond is observed. The crystal structure is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds and C-H⋯O inter-actions, which lead to the formation of a three-dimensional network.

Related literature

For the crystal structures of similar hydrazone compounds, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶); Zhi et al. (2011 ▶); Huang & Wu (2010 ▶).

Experimental

Crystal data

C15H14N2O3

M = 270.28

Orthorhombic,

a = 7.3872 (17) Å

b = 13.012 (2) Å

c = 13.592 (2) Å

V = 1306.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.981, T max = 0.984

6296 measured reflections

2663 independent reflections

1953 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.103

S = 0.99

2663 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.13 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: 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 datablock(s) global, I. DOI: 10.1107/S1600536811055930/su2356sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055930/su2356Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055930/su2356Isup3.cml

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

C15H14N2O3	F(000) = 568
Mr = 270.28	Dx = 1.374 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1375 reflections
a = 7.3872 (17) Å	θ = 2.6–24.5°
b = 13.012 (2) Å	µ = 0.10 mm−1
c = 13.592 (2) Å	T = 298 K
V = 1306.5 (4) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	2663 independent reflections
Radiation source: fine-focus sealed tube	1953 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 26.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→8
Tmin = 0.981, Tmax = 0.984	k = −13→16
6296 measured reflections	l = −17→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0494P)2] where P = (Fo2 + 2Fc2)/3
2663 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.13 e Å−3
0 restraints	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	0.0995 (3)	0.79013 (12)	0.51891 (12)	0.0453 (5)
N2	0.1159 (3)	0.72214 (12)	0.44083 (12)	0.0455 (5)
H2A	0.1404	0.7437	0.3825	0.055*
O1	0.1126 (2)	1.18743 (10)	0.79368 (10)	0.0516 (4)
H1	0.0544	1.1672	0.8412	0.077*
O2	0.0499 (2)	0.59172 (10)	0.54350 (10)	0.0523 (5)
O3	0.1334 (3)	0.40715 (11)	0.49251 (11)	0.0600 (5)
H3	0.1016	0.4528	0.5303	0.090*
C1	0.1268 (3)	0.96163 (14)	0.57681 (14)	0.0376 (5)
C2	0.0866 (3)	0.93585 (16)	0.67358 (15)	0.0430 (6)
H2	0.0608	0.8679	0.6894	0.052*
C3	0.0846 (3)	1.00949 (16)	0.74632 (14)	0.0433 (6)
H3A	0.0602	0.9908	0.8110	0.052*
C4	0.1188 (3)	1.11133 (14)	0.72333 (15)	0.0395 (5)
C5	0.1604 (3)	1.13823 (17)	0.62779 (15)	0.0479 (6)
H5	0.1856	1.2063	0.6121	0.057*
C6	0.1646 (3)	1.06390 (16)	0.55602 (16)	0.0457 (6)
H6	0.1935	1.0826	0.4919	0.055*
C7	0.1324 (3)	0.88408 (15)	0.49972 (15)	0.0424 (5)
H7	0.1604	0.9034	0.4356	0.051*
C8	0.0922 (3)	0.62132 (15)	0.45912 (15)	0.0410 (5)
C9	0.1136 (3)	0.54807 (15)	0.37750 (14)	0.0393 (5)
C10	0.1344 (3)	0.44378 (16)	0.39901 (15)	0.0437 (5)
C11	0.1573 (3)	0.37050 (17)	0.32441 (17)	0.0487 (6)
C12	0.1510 (3)	0.40437 (19)	0.22839 (17)	0.0541 (6)
H12	0.1634	0.3569	0.1777	0.065*
C13	0.1266 (3)	0.50748 (19)	0.20530 (17)	0.0537 (6)
H13	0.1215	0.5281	0.1399	0.064*
C14	0.1101 (3)	0.57847 (17)	0.27877 (15)	0.0465 (5)
H14	0.0964	0.6476	0.2630	0.056*
C15	0.1874 (4)	0.26079 (17)	0.35184 (19)	0.0692 (8)
H15A	0.2038	0.2206	0.2933	0.104*
H15B	0.0842	0.2357	0.3875	0.104*
H15C	0.2934	0.2555	0.3924	0.104*

	U11	U22	U33	U12	U13	U23
N1	0.0612 (13)	0.0413 (10)	0.0334 (10)	0.0007 (9)	0.0050 (9)	−0.0060 (7)
N2	0.0655 (13)	0.0413 (10)	0.0297 (9)	0.0004 (9)	0.0056 (10)	−0.0025 (8)
O1	0.0721 (12)	0.0415 (8)	0.0411 (8)	−0.0051 (8)	0.0055 (8)	−0.0065 (7)
O2	0.0801 (12)	0.0455 (9)	0.0312 (8)	−0.0016 (8)	0.0081 (8)	0.0011 (7)
O3	0.0948 (13)	0.0435 (9)	0.0416 (9)	0.0010 (10)	0.0016 (10)	0.0033 (7)
C1	0.0427 (12)	0.0367 (11)	0.0335 (11)	0.0039 (10)	−0.0002 (10)	0.0008 (9)
C2	0.0518 (14)	0.0346 (11)	0.0427 (12)	−0.0004 (10)	0.0029 (11)	0.0039 (10)
C3	0.0576 (16)	0.0410 (12)	0.0313 (11)	0.0001 (10)	0.0038 (11)	0.0010 (9)
C4	0.0436 (13)	0.0366 (11)	0.0383 (12)	0.0026 (10)	0.0018 (11)	−0.0053 (9)
C5	0.0598 (15)	0.0362 (11)	0.0475 (14)	−0.0068 (10)	0.0091 (12)	0.0031 (10)
C6	0.0579 (15)	0.0453 (13)	0.0339 (11)	0.0019 (11)	0.0046 (12)	0.0053 (10)
C7	0.0469 (13)	0.0434 (13)	0.0368 (12)	0.0037 (11)	0.0051 (11)	−0.0005 (10)
C8	0.0458 (13)	0.0425 (12)	0.0347 (12)	−0.0010 (10)	−0.0004 (11)	0.0019 (9)
C9	0.0429 (12)	0.0411 (11)	0.0340 (11)	−0.0024 (10)	−0.0009 (11)	−0.0042 (9)
C10	0.0491 (14)	0.0453 (12)	0.0365 (12)	−0.0060 (11)	−0.0005 (11)	−0.0023 (10)
C11	0.0458 (14)	0.0508 (14)	0.0495 (14)	−0.0061 (11)	0.0031 (11)	−0.0102 (11)
C12	0.0519 (15)	0.0624 (16)	0.0481 (14)	−0.0065 (12)	0.0039 (12)	−0.0237 (12)
C13	0.0602 (16)	0.0687 (16)	0.0322 (12)	−0.0023 (14)	0.0010 (12)	−0.0033 (11)
C14	0.0520 (14)	0.0515 (13)	0.0360 (12)	0.0003 (11)	−0.0003 (11)	0.0011 (10)
C15	0.083 (2)	0.0445 (14)	0.0800 (19)	−0.0051 (13)	0.0022 (16)	−0.0157 (13)

N1—C7	1.273 (2)	C5—H5	0.9300
N1—N2	1.387 (2)	C6—H6	0.9300
N2—C8	1.347 (2)	C7—H7	0.9300
N2—H2A	0.8600	C8—C9	1.471 (3)
O1—C4	1.377 (2)	C9—C10	1.397 (3)
O1—H1	0.8200	C9—C14	1.399 (3)
O2—C8	1.249 (2)	C10—C11	1.402 (3)
O3—C10	1.357 (2)	C11—C12	1.378 (3)
O3—H3	0.8200	C11—C15	1.492 (3)
C1—C6	1.389 (3)	C12—C13	1.390 (3)
C1—C2	1.389 (3)	C12—H12	0.9300
C1—C7	1.455 (3)	C13—C14	1.366 (3)
C2—C3	1.377 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.385 (3)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.380 (3)	C15—H15C	0.9600
C5—C6	1.374 (3)
C7—N1—N2	116.04 (18)	O2—C8—N2	120.15 (18)
C8—N2—N1	117.96 (17)	O2—C8—C9	121.28 (18)
C8—N2—H2A	121.0	N2—C8—C9	118.56 (18)
N1—N2—H2A	121.0	C10—C9—C14	118.51 (19)
C4—O1—H1	109.5	C10—C9—C8	118.92 (18)
C10—O3—H3	109.5	C14—C9—C8	122.55 (18)
C6—C1—C2	117.84 (18)	O3—C10—C9	122.45 (19)
C6—C1—C7	120.81 (18)	O3—C10—C11	116.04 (19)
C2—C1—C7	121.34 (18)	C9—C10—C11	121.5 (2)
C3—C2—C1	120.93 (18)	C12—C11—C10	117.6 (2)
C3—C2—H2	119.5	C12—C11—C15	123.2 (2)
C1—C2—H2	119.5	C10—C11—C15	119.2 (2)
C2—C3—C4	120.13 (19)	C11—C12—C13	121.8 (2)
C2—C3—H3A	119.9	C11—C12—H12	119.1
C4—C3—H3A	119.9	C13—C12—H12	119.1
O1—C4—C5	118.58 (18)	C14—C13—C12	120.0 (2)
O1—C4—C3	121.69 (18)	C14—C13—H13	120.0
C5—C4—C3	119.73 (18)	C12—C13—H13	120.0
C6—C5—C4	119.64 (19)	C13—C14—C9	120.6 (2)
C6—C5—H5	120.2	C13—C14—H14	119.7
C4—C5—H5	120.2	C9—C14—H14	119.7
C5—C6—C1	121.70 (19)	C11—C15—H15A	109.5
C5—C6—H6	119.1	C11—C15—H15B	109.5
C1—C6—H6	119.1	H15A—C15—H15B	109.5
N1—C7—C1	120.85 (19)	C11—C15—H15C	109.5
N1—C7—H7	119.6	H15A—C15—H15C	109.5
C1—C7—H7	119.6	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.86	2.575 (2)	146
O1—H1···O2i	0.82	2.00	2.809 (2)	167
N2—H2A···O1ii	0.86	2.36	3.067 (2)	139
C3—H3A···O2i	0.93	2.51	3.208 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.86	2.575 (2)	146
O1—H1⋯O2i	0.82	2.00	2.809 (2)	167
N2—H2A⋯O1ii	0.86	2.36	3.067 (2)	139
C3—H3A⋯O2i	0.93	2.51	3.208 (2)	132

Symmetry codes: (i) ; (ii) .