2,4-Dihydr-oxy-N'-(2-hydr-oxy-4-methoxy-benzyl-idene)benzohydrazide.

In the title compound, C(15)H(14)N(2)O(5), the dihedral angle between the two benzene rings is 4.3 (3)° and the mol-ecule adopts an E configuration with respect to the C=N bond. Intra-molecular O-H⋯N and N-H⋯O hydrogen bonds are observed. In the crystal structure, the mol-ecules are linked through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds to form layers parallel to the ac plane.

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 ▶); Cukurovali et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Lin & Sang (2009 ▶); Suleiman Gwaram et al. (2010 ▶); Li & Ban (2009 ▶); Lo & Ng (2009 ▶); Ning & Xu (2009 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C15H14N2O5

M = 302.28

Monoclinic,

a = 10.560 (3) Å

b = 12.752 (3) Å

c = 11.313 (2) Å

β = 112.853 (3)°

V = 1403.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.30 × 0.27 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.968, T max = 0.973

7972 measured reflections

3030 independent reflections

1023 reflections with I > 2σ(I)

R int = 0.127

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.182

S = 0.74

3030 reflections

206 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.28 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/S1600536810012420/ci5074sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012420/ci5074Isup2.hkl

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

C15H14N2O5	F(000) = 632
Mr = 302.28	Dx = 1.430 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 691 reflections
a = 10.560 (3) Å	θ = 2.5–24.5°
b = 12.752 (3) Å	µ = 0.11 mm−1
c = 11.313 (2) Å	T = 298 K
β = 112.853 (3)°	Block, colourless
V = 1403.8 (6) Å3	0.30 × 0.27 × 0.25 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3030 independent reflections
Radiation source: fine-focus sealed tube	1023 reflections with I > 2σ(I)
graphite	Rint = 0.127
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→13
Tmin = 0.968, Tmax = 0.973	k = −16→16
7972 measured reflections	l = −14→9

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 0.74	w = 1/[σ2(Fo2) + (0.0795P)2] where P = (Fo2 + 2Fc2)/3
3030 reflections	(Δ/σ)max = 0.001
206 parameters	Δρmax = 0.24 e Å−3
1 restraint	Δρmin = −0.28 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
N1	0.6400 (2)	0.2494 (2)	0.3907 (3)	0.0457 (8)
N2	0.4991 (3)	0.2654 (2)	0.3472 (3)	0.0472 (8)
O1	0.8985 (2)	0.2824 (2)	0.5431 (3)	0.0609 (8)
H1	0.8162	0.2961	0.5104	0.091*
O2	1.2425 (2)	0.08925 (18)	0.4832 (2)	0.0563 (7)
O3	0.5297 (2)	0.36628 (17)	0.5199 (2)	0.0504 (7)
O4	0.23759 (19)	0.21715 (19)	0.2060 (2)	0.0505 (7)
H4	0.1705	0.1952	0.1455	0.076*
O5	−0.1093 (2)	0.4346 (2)	0.2541 (3)	0.0650 (8)
H5	−0.1518	0.4218	0.1778	0.097*
C1	0.8268 (3)	0.1629 (3)	0.3636 (3)	0.0391 (9)
C2	0.9293 (3)	0.2101 (3)	0.4705 (3)	0.0407 (9)
C3	1.0660 (3)	0.1834 (3)	0.5062 (3)	0.0446 (9)
H3	1.1327	0.2147	0.5775	0.054*
C4	1.1035 (3)	0.1099 (3)	0.4356 (3)	0.0432 (9)
C5	1.0068 (3)	0.0628 (3)	0.3298 (4)	0.0478 (10)
H5A	1.0325	0.0140	0.2822	0.057*
C6	0.8696 (3)	0.0899 (3)	0.2955 (4)	0.0492 (10)
H6	0.8038	0.0580	0.2242	0.059*
C7	1.2890 (3)	0.0103 (3)	0.4192 (4)	0.0709 (13)
H7A	1.2419	−0.0543	0.4179	0.106*
H7B	1.3861	0.0002	0.4639	0.106*
H7C	1.2700	0.0322	0.3328	0.106*
C8	0.6814 (3)	0.1853 (3)	0.3265 (3)	0.0435 (9)
H8	0.6174	0.1524	0.2548	0.052*
C9	0.4506 (3)	0.3273 (3)	0.4183 (4)	0.0415 (9)
C10	0.3002 (3)	0.3483 (2)	0.3673 (3)	0.0374 (9)
C11	0.1983 (3)	0.2962 (3)	0.2647 (3)	0.0370 (8)
C12	0.0617 (3)	0.3252 (2)	0.2260 (3)	0.0419 (9)
H12	−0.0052	0.2916	0.1569	0.050*
C13	0.0249 (3)	0.4037 (3)	0.2898 (4)	0.0437 (9)
C14	0.1218 (3)	0.4546 (3)	0.3917 (4)	0.0519 (10)
H14	0.0958	0.5076	0.4343	0.062*
C15	0.2581 (3)	0.4264 (2)	0.4305 (4)	0.0457 (9)
H15	0.3235	0.4603	0.5004	0.055*
H2	0.443 (3)	0.241 (3)	0.2685 (18)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0189 (15)	0.0627 (19)	0.050 (2)	0.0027 (12)	0.0073 (13)	−0.0013 (16)
N2	0.0205 (15)	0.068 (2)	0.048 (2)	0.0037 (13)	0.0070 (14)	−0.0070 (17)
O1	0.0297 (13)	0.0741 (17)	0.0720 (19)	0.0085 (13)	0.0121 (13)	−0.0242 (16)
O2	0.0291 (13)	0.0700 (17)	0.0685 (19)	0.0128 (11)	0.0176 (12)	−0.0086 (15)
O3	0.0308 (12)	0.0562 (15)	0.0506 (17)	0.0006 (11)	0.0010 (12)	−0.0063 (14)
O4	0.0261 (12)	0.0640 (16)	0.0546 (18)	0.0019 (12)	0.0083 (12)	−0.0129 (14)
O5	0.0297 (13)	0.0760 (18)	0.082 (2)	0.0135 (13)	0.0131 (13)	−0.0088 (17)
C1	0.0244 (17)	0.049 (2)	0.042 (2)	−0.0017 (15)	0.0103 (16)	0.0014 (19)
C2	0.0298 (18)	0.045 (2)	0.049 (2)	0.0039 (16)	0.0172 (17)	−0.0038 (19)
C3	0.0260 (18)	0.057 (2)	0.047 (2)	0.0004 (16)	0.0100 (16)	−0.008 (2)
C4	0.0302 (18)	0.051 (2)	0.054 (2)	0.0027 (16)	0.0217 (18)	0.003 (2)
C5	0.042 (2)	0.051 (2)	0.054 (3)	0.0009 (17)	0.0217 (19)	−0.010 (2)
C6	0.033 (2)	0.058 (2)	0.054 (2)	−0.0082 (17)	0.0142 (18)	−0.010 (2)
C7	0.050 (3)	0.082 (3)	0.085 (3)	0.024 (2)	0.031 (2)	−0.002 (3)
C8	0.0288 (19)	0.053 (2)	0.043 (2)	−0.0066 (15)	0.0084 (17)	0.0018 (19)
C9	0.0279 (18)	0.045 (2)	0.045 (2)	0.0013 (15)	0.0074 (18)	0.0103 (19)
C10	0.0237 (17)	0.044 (2)	0.043 (2)	0.0015 (15)	0.0110 (16)	0.0066 (18)
C11	0.0264 (17)	0.0429 (19)	0.041 (2)	−0.0007 (15)	0.0123 (16)	0.0046 (18)
C12	0.0237 (17)	0.047 (2)	0.049 (2)	−0.0006 (15)	0.0072 (16)	0.0019 (19)
C13	0.0239 (17)	0.048 (2)	0.056 (2)	0.0062 (15)	0.0119 (17)	0.006 (2)
C14	0.040 (2)	0.049 (2)	0.067 (3)	0.0041 (17)	0.021 (2)	−0.008 (2)
C15	0.0331 (19)	0.045 (2)	0.053 (2)	−0.0009 (16)	0.0104 (17)	−0.004 (2)

N1—C8	1.278 (4)	C4—C5	1.374 (4)
N1—N2	1.389 (3)	C5—C6	1.390 (4)
N2—C9	1.362 (4)	C5—H5A	0.93
N2—H2	0.911 (10)	C6—H6	0.93
O1—C2	1.355 (4)	C7—H7A	0.96
O1—H1	0.82	C7—H7B	0.96
O2—C4	1.378 (3)	C7—H7C	0.96
O2—C7	1.434 (4)	C8—H8	0.93
O3—C9	1.232 (4)	C9—C10	1.488 (4)
O4—C11	1.357 (4)	C10—C15	1.397 (4)
O4—H4	0.82	C10—C11	1.406 (4)
O5—C13	1.372 (3)	C11—C12	1.386 (4)
O5—H5	0.82	C12—C13	1.375 (4)
C1—C6	1.390 (4)	C12—H12	0.93
C1—C2	1.407 (4)	C13—C14	1.372 (4)
C1—C8	1.455 (4)	C14—C15	1.380 (4)
C2—C3	1.382 (4)	C14—H14	0.93
C3—C4	1.385 (4)	C15—H15	0.93
C3—H3	0.93
C8—N1—N2	116.6 (3)	H7A—C7—H7B	109.5
C9—N2—N1	118.2 (3)	O2—C7—H7C	109.5
C9—N2—H2	122 (2)	H7A—C7—H7C	109.5
N1—N2—H2	120 (2)	H7B—C7—H7C	109.5
C2—O1—H1	109.5	N1—C8—C1	121.1 (3)
C4—O2—C7	117.3 (3)	N1—C8—H8	119.4
C11—O4—H4	109.5	C1—C8—H8	119.4
C13—O5—H5	109.5	O3—C9—N2	120.7 (3)
C6—C1—C2	117.1 (3)	O3—C9—C10	121.6 (3)
C6—C1—C8	120.3 (3)	N2—C9—C10	117.7 (3)
C2—C1—C8	122.5 (3)	C15—C10—C11	117.8 (3)
O1—C2—C3	117.4 (3)	C15—C10—C9	115.7 (3)
O1—C2—C1	121.7 (3)	C11—C10—C9	126.5 (3)
C3—C2—C1	120.9 (3)	O4—C11—C12	121.5 (3)
C2—C3—C4	119.9 (3)	O4—C11—C10	118.3 (3)
C2—C3—H3	120.0	C12—C11—C10	120.2 (3)
C4—C3—H3	120.0	C13—C12—C11	120.0 (3)
C5—C4—O2	125.1 (3)	C13—C12—H12	120.0
C5—C4—C3	121.0 (3)	C11—C12—H12	120.0
O2—C4—C3	113.8 (3)	O5—C13—C14	117.4 (3)
C4—C5—C6	118.4 (3)	O5—C13—C12	121.6 (3)
C4—C5—H5A	120.8	C14—C13—C12	121.0 (3)
C6—C5—H5A	120.8	C13—C14—C15	119.3 (3)
C5—C6—C1	122.7 (3)	C13—C14—H14	120.4
C5—C6—H6	118.7	C15—C14—H14	120.4
C1—C6—H6	118.7	C14—C15—C10	121.6 (3)
O2—C7—H7A	109.5	C14—C15—H15	119.2
O2—C7—H7B	109.5	C10—C15—H15	119.2

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.635 (3)	145
N2—H2···O4	0.91 (1)	2.03 (3)	2.670 (3)	126 (3)
N2—H2···O1i	0.91 (1)	2.43 (2)	3.240 (4)	149 (3)
O5—H5···O2ii	0.82	2.05	2.865 (4)	172
O4—H4···O3i	0.82	1.79	2.607 (3)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.92	2.635 (3)	145
N2—H2⋯O4	0.91 (1)	2.03 (3)	2.670 (3)	126 (3)
N2—H2⋯O1i	0.91 (1)	2.43 (2)	3.240 (4)	149 (3)
O5—H5⋯O2ii	0.82	2.05	2.865 (4)	172
O4—H4⋯O3i	0.82	1.79	2.607 (3)	174

Symmetry codes: (i) ; (ii) .