N'-(4-Hy-droxy-benzyl-idene)-3-meth-oxy-benzohydrazide.

In the title compound, C(15)H(14)N(2)O(3), the dihedral angle between the two benzene rings is 47.9 (3)°. In the crystal, mol-ecules are linked through N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds, forming layers parallel to the ab plane.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶, 2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14N2O3

M = 270.28

Orthorhombic,

a = 13.221 (2) Å

b = 9.5336 (18) Å

c = 21.620 (2) Å

V = 2725.1 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.982

18234 measured reflections

2531 independent reflections

1805 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.117

S = 1.11

2531 reflections

188 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055565/cv5225sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055565/cv5225Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055565/cv5225Isup3.cml

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

C15H14N2O3	Dx = 1.318 Mg m−3
Mr = 270.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2706 reflections
a = 13.221 (2) Å	θ = 2.4–24.6°
b = 9.5336 (18) Å	µ = 0.09 mm−1
c = 21.620 (2) Å	T = 298 K
V = 2725.1 (7) Å3	Cut from needle, colorless
Z = 8	0.23 × 0.21 × 0.20 mm
F(000) = 1136

Bruker SMART CCD area-detector diffractometer	2531 independent reflections
Radiation source: fine-focus sealed tube	1805 reflections with I > 2σ(I)
graphite	Rint = 0.069
ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.979, Tmax = 0.982	k = −11→11
18234 measured reflections	l = −22→26

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.041P)2 + 0.712P] where P = (Fo2 + 2Fc2)/3
2531 reflections	(Δ/σ)max < 0.001
188 parameters	Δρmax = 0.18 e Å−3
2 restraints	Δρmin = −0.20 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 > 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	0.84363 (13)	0.96516 (19)	0.63698 (8)	0.0335 (5)
N2	0.76637 (13)	0.89157 (18)	0.60808 (9)	0.0331 (5)
O1	1.24869 (13)	1.15604 (17)	0.77207 (8)	0.0491 (5)
O2	0.67126 (11)	1.08925 (16)	0.60246 (8)	0.0416 (4)
O3	0.31857 (12)	0.8832 (2)	0.55817 (10)	0.0676 (6)
C1	1.00898 (16)	0.9639 (2)	0.68058 (11)	0.0327 (5)
C2	1.02194 (17)	1.1091 (2)	0.67981 (12)	0.0390 (6)
H2A	0.9757	1.1648	0.6586	0.047*
C3	1.10217 (17)	1.1714 (2)	0.70994 (11)	0.0414 (6)
H3	1.1102	1.2682	0.7084	0.050*
C4	1.17085 (16)	1.0898 (2)	0.74251 (11)	0.0340 (6)
C5	1.16016 (17)	0.9463 (2)	0.74303 (11)	0.0378 (6)
H5	1.2064	0.8911	0.7645	0.045*
C6	1.08096 (16)	0.8842 (2)	0.71180 (12)	0.0384 (6)
H6	1.0755	0.7869	0.7116	0.046*
C7	0.92309 (16)	0.8958 (2)	0.65072 (11)	0.0338 (6)
H7	0.9263	0.8005	0.6416	0.041*
C8	0.68050 (16)	0.9628 (2)	0.59326 (10)	0.0311 (5)
C9	0.59785 (15)	0.8768 (2)	0.56562 (10)	0.0300 (5)
C10	0.49867 (16)	0.9232 (2)	0.57510 (11)	0.0365 (6)
H10	0.4868	1.0042	0.5980	0.044*
C11	0.41857 (17)	0.8491 (3)	0.55060 (12)	0.0429 (6)
C12	0.43747 (19)	0.7307 (3)	0.51536 (13)	0.0495 (7)
H12	0.3837	0.6808	0.4985	0.059*
C13	0.53502 (19)	0.6863 (3)	0.50505 (12)	0.0463 (7)
H13	0.5467	0.6076	0.4807	0.056*
C14	0.61629 (17)	0.7580 (2)	0.53071 (10)	0.0375 (6)
H14	0.6821	0.7266	0.5245	0.045*
C15	0.2946 (2)	1.0000 (4)	0.59606 (15)	0.0752 (10)
H15A	0.3231	0.9867	0.6365	0.113*
H15B	0.2224	1.0087	0.5994	0.113*
H15C	0.3219	1.0838	0.5779	0.113*
H2	0.770 (2)	0.7974 (11)	0.6051 (14)	0.090*
H1	1.276 (2)	1.104 (3)	0.7996 (13)	0.113*

	U11	U22	U33	U12	U13	U23
N1	0.0297 (10)	0.0310 (10)	0.0398 (12)	−0.0013 (9)	−0.0022 (9)	−0.0029 (9)
N2	0.0288 (10)	0.0267 (10)	0.0439 (12)	−0.0026 (9)	−0.0047 (9)	−0.0049 (9)
O1	0.0510 (10)	0.0357 (10)	0.0607 (13)	−0.0157 (8)	−0.0214 (10)	0.0127 (9)
O2	0.0395 (9)	0.0267 (9)	0.0587 (12)	0.0026 (7)	−0.0059 (8)	−0.0060 (8)
O3	0.0298 (10)	0.0944 (16)	0.0784 (15)	−0.0011 (10)	−0.0039 (10)	−0.0058 (13)
C1	0.0298 (12)	0.0289 (12)	0.0393 (14)	0.0024 (10)	0.0001 (11)	0.0002 (11)
C2	0.0347 (13)	0.0336 (13)	0.0486 (16)	0.0032 (11)	−0.0085 (11)	0.0082 (12)
C3	0.0468 (15)	0.0241 (12)	0.0532 (17)	−0.0039 (11)	−0.0067 (13)	0.0065 (12)
C4	0.0332 (12)	0.0319 (12)	0.0370 (14)	−0.0054 (10)	−0.0027 (11)	0.0053 (11)
C5	0.0375 (13)	0.0275 (12)	0.0483 (16)	0.0020 (10)	−0.0085 (12)	0.0070 (11)
C6	0.0391 (13)	0.0218 (12)	0.0544 (17)	−0.0015 (10)	−0.0041 (12)	0.0001 (11)
C7	0.0346 (13)	0.0261 (12)	0.0406 (15)	−0.0007 (10)	−0.0007 (11)	−0.0012 (11)
C8	0.0320 (12)	0.0305 (13)	0.0307 (14)	0.0004 (10)	0.0033 (10)	0.0018 (11)
C9	0.0305 (12)	0.0274 (12)	0.0322 (14)	−0.0029 (9)	−0.0020 (10)	0.0049 (11)
C10	0.0357 (13)	0.0350 (13)	0.0389 (15)	0.0000 (10)	−0.0014 (11)	0.0012 (11)
C11	0.0317 (13)	0.0542 (16)	0.0427 (16)	−0.0045 (12)	−0.0032 (12)	0.0085 (13)
C12	0.0420 (15)	0.0547 (17)	0.0518 (18)	−0.0145 (13)	−0.0148 (13)	0.0015 (14)
C13	0.0521 (16)	0.0382 (14)	0.0486 (17)	−0.0050 (12)	−0.0090 (14)	−0.0092 (12)
C14	0.0356 (13)	0.0344 (13)	0.0426 (15)	−0.0008 (11)	−0.0021 (11)	−0.0028 (12)
C15	0.0442 (17)	0.107 (3)	0.074 (2)	0.0198 (17)	0.0123 (16)	0.008 (2)

N1—C7	1.277 (3)	C5—H5	0.9300
N1—N2	1.388 (2)	C6—H6	0.9300
N2—C8	1.361 (3)	C7—H7	0.9300
N2—H2	0.901 (10)	C8—C9	1.491 (3)
O1—C4	1.366 (3)	C9—C14	1.382 (3)
O1—H1	0.853 (10)	C9—C10	1.399 (3)
O2—C8	1.228 (2)	C10—C11	1.379 (3)
O3—C11	1.371 (3)	C10—H10	0.9300
O3—C15	1.419 (3)	C11—C12	1.384 (4)
C1—C6	1.392 (3)	C12—C13	1.376 (3)
C1—C2	1.395 (3)	C12—H12	0.9300
C1—C7	1.459 (3)	C13—C14	1.389 (3)
C2—C3	1.379 (3)	C13—H13	0.9300
C2—H2A	0.9300	C14—H14	0.9300
C3—C4	1.387 (3)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.376 (3)	C15—H15C	0.9600
C5—C6	1.379 (3)
C7—N1—N2	116.64 (18)	O2—C8—N2	122.3 (2)
C8—N2—N1	117.87 (17)	O2—C8—C9	122.15 (19)
C8—N2—H2	121.7 (19)	N2—C8—C9	115.51 (19)
N1—N2—H2	119.8 (19)	C14—C9—C10	120.3 (2)
C4—O1—H1	112 (2)	C14—C9—C8	122.69 (19)
C11—O3—C15	118.1 (2)	C10—C9—C8	117.0 (2)
C6—C1—C2	117.6 (2)	C11—C10—C9	120.1 (2)
C6—C1—C7	120.3 (2)	C11—C10—H10	120.0
C2—C1—C7	122.1 (2)	C9—C10—H10	120.0
C3—C2—C1	121.1 (2)	O3—C11—C10	125.0 (2)
C3—C2—H2A	119.5	O3—C11—C12	115.7 (2)
C1—C2—H2A	119.5	C10—C11—C12	119.4 (2)
C2—C3—C4	120.1 (2)	C13—C12—C11	120.6 (2)
C2—C3—H3	119.9	C13—C12—H12	119.7
C4—C3—H3	119.9	C11—C12—H12	119.7
O1—C4—C5	122.2 (2)	C12—C13—C14	120.6 (2)
O1—C4—C3	118.13 (19)	C12—C13—H13	119.7
C5—C4—C3	119.6 (2)	C14—C13—H13	119.7
C4—C5—C6	120.1 (2)	C9—C14—C13	119.0 (2)
C4—C5—H5	120.0	C9—C14—H14	120.5
C6—C5—H5	120.0	C13—C14—H14	120.5
C5—C6—C1	121.5 (2)	O3—C15—H15A	109.5
C5—C6—H6	119.3	O3—C15—H15B	109.5
C1—C6—H6	119.3	H15A—C15—H15B	109.5
N1—C7—C1	120.9 (2)	O3—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
N2—H2···O2i	0.90 (1)	2.13 (1)	3.000 (2)	162 (3)
O1—H1···N1ii	0.85 (1)	2.11 (1)	2.959 (2)	176 (3)
O1—H1···O2ii	0.85 (1)	2.53 (3)	2.969 (2)	113 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.90 (1)	2.13 (1)	3.000 (2)	162 (3)
O1—H1⋯N1ii	0.85 (1)	2.11 (1)	2.959 (2)	176 (3)
O1—H1⋯O2ii	0.85 (1)	2.53 (3)	2.969 (2)	113 (3)

Symmetry codes: (i) ; (ii) .