N'-(2,5-Dihydroxy-benzyl-idene)-2-hydr-oxy-3-methyl-benzohydrazide.

In the title compound, C(15)H(14)N(2)O(4), the dihedral angle between the two benzene rings is 4.1 (2)°. The mol-ecule adopts an E configuration with respect to the C=N bond. There are intra-molecular O-H⋯N and O-H⋯O hydrogen bonds in the mol-ecule. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 ▶); Cukurovali et al. (2006 ▶). For the crystal structures of hydrazones, see: Mohd Lair et al. (2009 ▶); Lin & Sang (2009 ▶); Suleiman Gwaram et al. (2010 ▶). For hydrazone compounds recently reported by us, see: Han & Zhao (2010a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). For similar compounds, see: Li & Ban (2009 ▶); Lo & Ng (2009 ▶); Ning & Xu (2009 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C15H14N2O4

M = 286.28

Monoclinic,

a = 13.333 (2) Å

b = 7.316 (1) Å

c = 13.738 (2) Å

β = 94.742 (2)°

V = 1335.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.25 × 0.23 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.974, T max = 0.977

7636 measured reflections

3002 independent reflections

1457 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.136

S = 0.82

3002 reflections

197 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.26 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/S1600536810013395/om2333sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013395/om2333Isup2.hkl

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

C15H14N2O4	F(000) = 600
Mr = 286.28	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.333 (2) Å	Cell parameters from 1316 reflections
b = 7.316 (1) Å	θ = 2.7–24.5°
c = 13.738 (2) Å	µ = 0.11 mm−1
β = 94.742 (2)°	T = 298 K
V = 1335.5 (3) Å3	Block, colorless
Z = 4	0.25 × 0.23 × 0.22 mm

Bruker SMART CCD area-detector diffractometer	3002 independent reflections
Radiation source: fine-focus sealed tube	1457 reflections with I > 2σ(I)
graphite	Rint = 0.087
ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→16
Tmin = 0.974, Tmax = 0.977	k = −9→9
7636 measured reflections	l = −11→17

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 0.82	w = 1/[σ2(Fo2) + (0.0615P)2] where P = (Fo2 + 2Fc2)/3
3002 reflections	(Δ/σ)max = 0.001
197 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.26 e Å−3

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 > 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	0.25674 (12)	0.4205 (2)	0.31421 (10)	0.0660 (5)
H1	0.2036	0.3785	0.2893	0.099*
O2	0.12591 (10)	0.3298 (2)	0.17731 (10)	0.0530 (4)
O3	−0.10549 (10)	0.1488 (2)	0.03610 (9)	0.0528 (4)
H3	−0.0498	0.1958	0.0467	0.079*
O4	−0.22237 (11)	0.1219 (2)	−0.35891 (9)	0.0555 (4)
H4	−0.1937	0.2007	−0.3888	0.083*
N1	0.15386 (12)	0.3685 (2)	0.01891 (11)	0.0451 (4)
H1A	0.1913 (15)	0.405 (3)	−0.0290 (12)	0.080*
N2	0.06052 (11)	0.2950 (2)	−0.00814 (11)	0.0441 (4)
C1	0.28436 (13)	0.4534 (3)	0.14397 (13)	0.0401 (5)
C2	0.31477 (14)	0.4737 (3)	0.24325 (14)	0.0447 (5)
C3	0.40822 (15)	0.5532 (3)	0.27436 (15)	0.0513 (6)
C4	0.46896 (16)	0.6081 (3)	0.20408 (17)	0.0573 (6)
H4A	0.5310	0.6606	0.2235	0.069*
C5	0.44147 (15)	0.5884 (3)	0.10597 (16)	0.0570 (6)
H5	0.4846	0.6271	0.0602	0.068*
C6	0.34987 (14)	0.5113 (3)	0.07559 (14)	0.0496 (5)
H6	0.3315	0.4976	0.0092	0.060*
C7	0.43835 (18)	0.5770 (4)	0.38160 (16)	0.0771 (8)
H7A	0.5062	0.6219	0.3903	0.116*
H7B	0.4342	0.4615	0.4142	0.116*
H7C	0.3939	0.6628	0.4088	0.116*
C8	0.18276 (14)	0.3793 (3)	0.11571 (14)	0.0412 (5)
C9	0.03111 (14)	0.2882 (3)	−0.09837 (14)	0.0436 (5)
H9	0.0720	0.3335	−0.1444	0.052*
C10	−0.06605 (13)	0.2097 (3)	−0.12963 (13)	0.0385 (5)
C11	−0.13067 (14)	0.1425 (3)	−0.06259 (13)	0.0404 (5)
C12	−0.22281 (14)	0.0702 (3)	−0.09566 (15)	0.0470 (5)
H12	−0.2653	0.0246	−0.0511	0.056*
C13	−0.25242 (14)	0.0648 (3)	−0.19390 (14)	0.0462 (5)
H13	−0.3150	0.0168	−0.2152	0.055*
C14	−0.18970 (14)	0.1304 (3)	−0.26101 (13)	0.0413 (5)
C15	−0.09706 (13)	0.2005 (3)	−0.22897 (13)	0.0418 (5)
H15	−0.0544	0.2425	−0.2743	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0648 (10)	0.0952 (13)	0.0377 (8)	−0.0074 (9)	0.0018 (7)	0.0016 (8)
O2	0.0484 (8)	0.0677 (10)	0.0431 (8)	−0.0063 (7)	0.0044 (7)	0.0013 (7)
O3	0.0568 (9)	0.0703 (10)	0.0313 (8)	−0.0052 (8)	0.0034 (6)	0.0003 (7)
O4	0.0528 (9)	0.0748 (12)	0.0365 (8)	−0.0068 (7)	−0.0098 (7)	−0.0039 (7)
N1	0.0382 (9)	0.0598 (12)	0.0362 (10)	−0.0042 (8)	−0.0040 (7)	−0.0021 (8)
N2	0.0398 (9)	0.0505 (11)	0.0403 (10)	−0.0002 (7)	−0.0068 (7)	−0.0037 (8)
C1	0.0392 (10)	0.0443 (12)	0.0356 (11)	0.0047 (9)	−0.0037 (9)	−0.0008 (9)
C2	0.0458 (11)	0.0502 (13)	0.0375 (11)	0.0054 (10)	−0.0001 (9)	0.0005 (9)
C3	0.0493 (12)	0.0555 (14)	0.0463 (13)	0.0090 (10)	−0.0138 (10)	−0.0075 (11)
C4	0.0376 (11)	0.0633 (16)	0.0685 (16)	0.0023 (10)	−0.0098 (11)	−0.0054 (12)
C5	0.0404 (12)	0.0762 (16)	0.0538 (14)	−0.0035 (11)	0.0004 (10)	0.0049 (12)
C6	0.0447 (11)	0.0667 (15)	0.0364 (11)	0.0021 (11)	−0.0031 (9)	−0.0001 (10)
C7	0.0754 (16)	0.098 (2)	0.0525 (15)	0.0085 (14)	−0.0247 (13)	−0.0169 (14)
C8	0.0413 (11)	0.0435 (12)	0.0378 (11)	0.0035 (9)	−0.0024 (9)	−0.0022 (9)
C9	0.0392 (11)	0.0523 (13)	0.0389 (12)	0.0015 (9)	0.0011 (9)	−0.0034 (10)
C10	0.0371 (10)	0.0439 (12)	0.0342 (11)	0.0028 (9)	0.0005 (8)	−0.0039 (9)
C11	0.0456 (11)	0.0445 (12)	0.0305 (11)	0.0037 (9)	−0.0006 (9)	−0.0016 (9)
C12	0.0446 (11)	0.0514 (13)	0.0456 (12)	−0.0002 (9)	0.0082 (10)	0.0012 (10)
C13	0.0354 (10)	0.0516 (13)	0.0505 (13)	−0.0042 (9)	−0.0023 (9)	−0.0051 (10)
C14	0.0399 (11)	0.0492 (12)	0.0337 (11)	0.0042 (9)	−0.0039 (9)	−0.0035 (9)
C15	0.0381 (11)	0.0549 (13)	0.0323 (11)	0.0000 (9)	0.0024 (8)	−0.0023 (9)

O1—C2	1.351 (2)	C4—H4A	0.9300
O1—H1	0.8200	C5—C6	1.378 (3)
O2—C8	1.236 (2)	C5—H5	0.9300
O3—C11	1.370 (2)	C6—H6	0.9300
O3—H3	0.8200	C7—H7A	0.9600
O4—C14	1.380 (2)	C7—H7B	0.9600
O4—H4	0.8200	C7—H7C	0.9600
N1—C8	1.356 (2)	C9—C10	1.449 (3)
N1—N2	1.378 (2)	C9—H9	0.9300
N1—H1A	0.899 (19)	C10—C15	1.395 (2)
N2—C9	1.270 (2)	C10—C11	1.401 (3)
C1—C2	1.398 (2)	C11—C12	1.379 (3)
C1—C6	1.400 (3)	C12—C13	1.375 (3)
C1—C8	1.481 (3)	C12—H12	0.9300
C2—C3	1.409 (3)	C13—C14	1.381 (3)
C3—C4	1.371 (3)	C13—H13	0.9300
C3—C7	1.505 (3)	C14—C15	1.376 (2)
C4—C5	1.375 (3)	C15—H15	0.9300
C2—O1—H1	109.5	C3—C7—H7C	109.5
C11—O3—H3	109.5	H7A—C7—H7C	109.5
C14—O4—H4	109.5	H7B—C7—H7C	109.5
C8—N1—N2	117.67 (16)	O2—C8—N1	120.92 (18)
C8—N1—H1A	124.8 (15)	O2—C8—C1	121.82 (17)
N2—N1—H1A	117.5 (15)	N1—C8—C1	117.26 (18)
C9—N2—N1	118.55 (16)	N2—C9—C10	120.09 (18)
C2—C1—C6	118.40 (17)	N2—C9—H9	120.0
C2—C1—C8	118.67 (18)	C10—C9—H9	120.0
C6—C1—C8	122.87 (17)	C15—C10—C11	118.53 (17)
O1—C2—C1	122.42 (18)	C15—C10—C9	119.64 (18)
O1—C2—C3	116.41 (18)	C11—C10—C9	121.83 (17)
C1—C2—C3	121.17 (19)	O3—C11—C12	118.53 (18)
C4—C3—C2	117.80 (18)	O3—C11—C10	121.64 (17)
C4—C3—C7	122.02 (19)	C12—C11—C10	119.82 (17)
C2—C3—C7	120.2 (2)	C13—C12—C11	120.65 (19)
C3—C4—C5	122.33 (19)	C13—C12—H12	119.7
C3—C4—H4A	118.8	C11—C12—H12	119.7
C5—C4—H4A	118.8	C12—C13—C14	120.31 (17)
C4—C5—C6	119.8 (2)	C12—C13—H13	119.8
C4—C5—H5	120.1	C14—C13—H13	119.8
C6—C5—H5	120.1	C15—C14—O4	122.08 (18)
C5—C6—C1	120.46 (19)	C15—C14—C13	119.55 (17)
C5—C6—H6	119.8	O4—C14—C13	118.36 (16)
C1—C6—H6	119.8	C14—C15—C10	121.11 (18)
C3—C7—H7A	109.5	C14—C15—H15	119.4
C3—C7—H7B	109.5	C10—C15—H15	119.4
H7A—C7—H7B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.82	2.5452 (19)	147
O3—H3···N2	0.82	1.85	2.576 (2)	146
O4—H4···O3i	0.82	1.97	2.774 (2)	169
N1—H1A···O4ii	0.90 (2)	2.27 (2)	3.072 (2)	148 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.82	2.5452 (19)	147
O3—H3⋯N2	0.82	1.85	2.576 (2)	146
O4—H4⋯O3i	0.82	1.97	2.774 (2)	169
N1—H1A⋯O4ii	0.90 (2)	2.27 (2)	3.072 (2)	148 (2)

Symmetry codes: (i) ; (ii) .