N'-[(E)-4-Hydr-oxy-3-methoxy-benzyl-idene]benzohydrazide.

In the title compound, C(15)H(14)N(2)O(3), the phenyl ring is disordered over two set of sites with an occupancy ratio of 0.810 (3):0.190 (3); the dihedral angle between the two components is 72.3 (4)°. The benzene and phenyl rings are oriented at dihedral angles of 69.18 (8) and 26.0 (5)° (major and minor orientations, respectively), and an intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked by N-H⋯O, O-H⋯O and C-H⋯O inter-actions, generating a three-dimensional network.

Related literature

For related structures, see: Shafiq et al. (2009a ▶,b ▶); Shi (2005 ▶).

Experimental

Crystal data

C15H14N2O3

M = 270.28

Tetragonal,

a = 18.6994 (8) Å

c = 15.7223 (12) Å

V = 5497.6 (5) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.28 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.976, T max = 0.979

15310 measured reflections

3393 independent reflections

1656 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.151

S = 0.99

3393 reflections

214 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (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: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044122/hb5175sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044122/hb5175Isup2.hkl

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

C15H14N2O3	Dx = 1.306 Mg m−3
Mr = 270.28	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 3393 reflections
Hall symbol: -I 4ad	θ = 1.7–28.3°
a = 18.6994 (8) Å	µ = 0.09 mm−1
c = 15.7223 (12) Å	T = 296 K
V = 5497.6 (5) Å3	Prism, colourless
Z = 16	0.28 × 0.24 × 0.22 mm
F(000) = 2272

Bruker Kappa APEXII CCD diffractometer	3393 independent reflections
Radiation source: fine-focus sealed tube	1656 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 1.7°
ω scans	h = −24→24
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −24→24
Tmin = 0.976, Tmax = 0.979	l = −20→20
15310 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.071P)2 + 0.721P] where P = (Fo2 + 2Fc2)/3
3393 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
O1	0.31015 (8)	0.09452 (8)	0.50043 (7)	0.0639 (5)
O2	−0.07897 (8)	−0.13841 (8)	0.63057 (9)	0.0715 (6)
O3	−0.00552 (9)	−0.02825 (9)	0.69117 (8)	0.0751 (6)
N1	0.23647 (9)	0.04528 (9)	0.40397 (9)	0.0577 (6)
N2	0.19267 (9)	0.01533 (10)	0.46558 (9)	0.0578 (6)
C1A	0.32949 (10)	0.12512 (10)	0.35611 (10)	0.0491 (15)	0.813 (3)
C2A	0.29168 (9)	0.15525 (12)	0.28897 (12)	0.0678 (10)	0.813 (3)
C3A	0.32797 (12)	0.19079 (13)	0.22442 (11)	0.0813 (15)	0.813 (3)
C4A	0.40207 (12)	0.19620 (12)	0.22701 (11)	0.0810 (16)	0.813 (3)
C5A	0.43989 (9)	0.16606 (11)	0.29416 (13)	0.0760 (12)	0.813 (3)
C6A	0.40360 (10)	0.13052 (10)	0.35871 (10)	0.0619 (10)	0.813 (3)
C7	0.29070 (11)	0.08778 (10)	0.42620 (10)	0.0495 (7)
C8	0.14721 (12)	−0.02955 (12)	0.43724 (12)	0.0584 (7)
C9	0.09173 (11)	−0.06060 (11)	0.49065 (11)	0.0550 (7)
C10	0.05165 (12)	−0.11712 (12)	0.46193 (12)	0.0638 (8)
C11	−0.00483 (12)	−0.14403 (11)	0.51003 (13)	0.0636 (8)
C12	−0.02232 (11)	−0.11260 (11)	0.58606 (12)	0.0559 (7)
C13	0.01804 (11)	−0.05554 (11)	0.61574 (11)	0.0564 (7)
C14	0.07470 (11)	−0.02999 (11)	0.56916 (11)	0.0576 (7)
C15	0.03358 (16)	0.02801 (17)	0.72880 (14)	0.0990 (11)
C2B	0.3203 (5)	0.1020 (4)	0.2723 (5)	0.059 (4)	0.187 (3)
C3B	0.3506 (6)	0.1424 (5)	0.2075 (4)	0.076 (5)	0.187 (3)
C4B	0.3772 (7)	0.2103 (5)	0.2246 (5)	0.078 (7)	0.187 (3)
C5B	0.3737 (6)	0.2377 (4)	0.3067 (6)	0.092 (6)	0.187 (3)
C6B	0.3434 (5)	0.1973 (4)	0.3716 (4)	0.070 (5)	0.187 (3)
C1B	0.3167 (5)	0.1294 (4)	0.3544 (4)	0.055 (7)	0.187 (3)
H5A	0.48947	0.16967	0.29590	0.0913*	0.813 (3)
H6A	0.42890	0.11036	0.40363	0.0743*	0.813 (3)
H10	0.06233	−0.13774	0.40962	0.0766*
H11	−0.03064	−0.18328	0.49061	0.0763*
H14	0.10184	0.00784	0.58997	0.0691*
H15A	0.03617	0.06754	0.68996	0.1486*
H15B	0.08102	0.01179	0.74192	0.1486*
H15C	0.01014	0.04298	0.78013	0.1486*
H8	0.14959	−0.04294	0.38034	0.0701*
H1	0.22866	0.03642	0.35111	0.0692*
H2	−0.08451	−0.11459	0.67387	0.1072*
H2A	0.24210	0.15164	0.28723	0.0814*	0.813 (3)
H3A	0.30267	0.21096	0.17949	0.0978*	0.813 (3)
H4A	0.42635	0.21997	0.18383	0.0970*	0.813 (3)
H2B	0.30242	0.05661	0.26082	0.0709*	0.187 (3)
H3B	0.35296	0.12407	0.15254	0.0912*	0.187 (3)
H4B	0.39750	0.23733	0.18123	0.0932*	0.187 (3)
H5B	0.39151	0.28312	0.31819	0.1097*	0.187 (3)
H6B	0.34098	0.21565	0.42646	0.0839*	0.187 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0871 (11)	0.0700 (10)	0.0346 (6)	−0.0024 (8)	−0.0072 (6)	−0.0015 (6)
O2	0.0768 (11)	0.0677 (11)	0.0699 (9)	−0.0116 (8)	0.0145 (8)	0.0004 (7)
O3	0.0816 (11)	0.0916 (12)	0.0521 (8)	−0.0187 (9)	0.0146 (7)	−0.0128 (7)
N1	0.0632 (11)	0.0790 (12)	0.0309 (7)	−0.0057 (9)	0.0011 (7)	0.0057 (7)
N2	0.0605 (11)	0.0739 (12)	0.0390 (8)	0.0006 (10)	0.0052 (7)	0.0098 (8)
C1A	0.064 (3)	0.050 (3)	0.0334 (19)	0.0030 (19)	−0.0007 (14)	−0.0007 (18)
C2A	0.0692 (19)	0.083 (2)	0.0512 (14)	−0.0108 (16)	−0.0127 (13)	0.0175 (14)
C3A	0.099 (3)	0.092 (3)	0.0528 (16)	−0.015 (2)	−0.0081 (18)	0.0242 (17)
C4A	0.105 (3)	0.068 (3)	0.070 (2)	−0.017 (2)	0.0224 (19)	−0.0005 (19)
C5A	0.064 (2)	0.077 (2)	0.087 (2)	−0.0071 (16)	0.0126 (16)	−0.0008 (16)
C6A	0.0558 (19)	0.0681 (19)	0.0618 (15)	0.0009 (13)	−0.0030 (12)	0.0011 (12)
C7	0.0602 (13)	0.0538 (12)	0.0346 (9)	0.0093 (10)	−0.0013 (8)	0.0004 (8)
C8	0.0648 (14)	0.0671 (14)	0.0433 (10)	0.0071 (11)	0.0044 (9)	0.0017 (9)
C9	0.0589 (13)	0.0566 (13)	0.0494 (10)	0.0046 (10)	0.0034 (9)	0.0041 (9)
C10	0.0740 (15)	0.0623 (15)	0.0552 (11)	0.0051 (12)	0.0086 (11)	−0.0063 (10)
C11	0.0727 (16)	0.0500 (13)	0.0680 (13)	−0.0021 (11)	0.0014 (11)	−0.0046 (10)
C12	0.0618 (14)	0.0516 (13)	0.0544 (11)	0.0014 (10)	0.0027 (10)	0.0070 (9)
C13	0.0640 (14)	0.0615 (14)	0.0437 (10)	0.0030 (11)	0.0025 (9)	0.0010 (9)
C14	0.0619 (14)	0.0634 (14)	0.0474 (10)	−0.0053 (10)	0.0008 (9)	0.0013 (9)
C15	0.110 (2)	0.127 (2)	0.0599 (14)	−0.0388 (18)	0.0150 (13)	−0.0343 (14)
C2B	0.053 (7)	0.058 (8)	0.067 (7)	−0.013 (6)	0.004 (5)	0.002 (6)
C3B	0.081 (10)	0.089 (11)	0.058 (7)	0.012 (9)	0.008 (6)	0.007 (7)
C4B	0.098 (15)	0.084 (14)	0.051 (9)	−0.001 (11)	0.026 (8)	0.008 (8)
C5B	0.094 (11)	0.063 (9)	0.118 (12)	−0.014 (8)	−0.003 (8)	−0.001 (8)
C6B	0.084 (9)	0.066 (9)	0.060 (6)	−0.011 (7)	0.000 (6)	−0.005 (6)
C1B	0.029 (7)	0.066 (15)	0.071 (14)	−0.016 (7)	−0.013 (7)	−0.013 (11)

O1—C7	1.229 (2)	C9—C14	1.397 (3)
O2—C12	1.358 (2)	C9—C10	1.372 (3)
O3—C13	1.364 (2)	C10—C11	1.393 (3)
O3—C15	1.411 (3)	C11—C12	1.372 (3)
O2—H2	0.8200	C12—C13	1.388 (3)
N1—N2	1.387 (2)	C13—C14	1.374 (3)
N1—C7	1.335 (3)	C2A—H2A	0.9300
N2—C8	1.275 (3)	C2B—H2B	0.9300
N1—H1	0.8600	C3A—H3A	0.9300
C1A—C6A	1.390 (3)	C3B—H3B	0.9300
C1A—C7	1.493 (2)	C4A—H4A	0.9300
C1A—C2A	1.390 (3)	C4B—H4B	0.9300
C1B—C2B	1.390 (10)	C5A—H5A	0.9300
C1B—C6B	1.391 (11)	C5B—H5B	0.9300
C1B—C7	1.455 (7)	C6A—H6A	0.9300
C2A—C3A	1.390 (3)	C6B—H6B	0.9300
C2B—C3B	1.389 (12)	C8—H8	0.9300
C3A—C4A	1.390 (3)	C10—H10	0.9300
C3B—C4B	1.390 (14)	C11—H11	0.9300
C4A—C5A	1.390 (3)	C14—H14	0.9300
C4B—C5B	1.390 (12)	C15—H15B	0.9600
C5A—C6A	1.390 (3)	C15—H15C	0.9600
C5B—C6B	1.390 (12)	C15—H15A	0.9600
C8—C9	1.456 (3)
C13—O3—C15	118.43 (18)	C12—C13—C14	120.50 (17)
C12—O2—H2	109.00	O3—C13—C12	113.85 (18)
N2—N1—C7	120.41 (14)	C9—C14—C13	120.28 (19)
N1—N2—C8	114.55 (15)	C1A—C2A—H2A	120.00
N2—N1—H1	120.00	C3A—C2A—H2A	120.00
C7—N1—H1	120.00	C1B—C2B—H2B	120.00
C2A—C1A—C6A	120.00 (16)	C3B—C2B—H2B	120.00
C2A—C1A—C7	120.21 (17)	C4A—C3A—H3A	120.00
C6A—C1A—C7	119.78 (15)	C2A—C3A—H3A	120.00
C2B—C1B—C6B	120.0 (7)	C4B—C3B—H3B	120.00
C2B—C1B—C7	122.6 (6)	C2B—C3B—H3B	120.00
C6B—C1B—C7	117.2 (5)	C3A—C4A—H4A	120.00
C1A—C2A—C3A	120.00 (17)	C5A—C4A—H4A	120.00
C1B—C2B—C3B	120.0 (7)	C5B—C4B—H4B	120.00
C2A—C3A—C4A	120.01 (18)	C3B—C4B—H4B	120.00
C2B—C3B—C4B	120.1 (7)	C6A—C5A—H5A	120.00
C3A—C4A—C5A	120.00 (18)	C4A—C5A—H5A	120.00
C3B—C4B—C5B	120.0 (8)	C4B—C5B—H5B	120.00
C4A—C5A—C6A	120.00 (17)	C6B—C5B—H5B	120.00
C4B—C5B—C6B	120.0 (8)	C1A—C6A—H6A	120.00
C1A—C6A—C5A	120.00 (16)	C5A—C6A—H6A	120.00
C1B—C6B—C5B	120.0 (6)	C5B—C6B—H6B	120.00
O1—C7—C1A	120.62 (18)	C1B—C6B—H6B	120.00
O1—C7—C1B	125.7 (3)	C9—C8—H8	119.00
O1—C7—N1	122.31 (17)	N2—C8—H8	119.00
N1—C7—C1A	117.02 (14)	C9—C10—H10	120.00
N1—C7—C1B	111.7 (3)	C11—C10—H10	120.00
N2—C8—C9	122.43 (17)	C12—C11—H11	120.00
C8—C9—C10	120.45 (17)	C10—C11—H11	120.00
C8—C9—C14	120.57 (18)	C13—C14—H14	120.00
C10—C9—C14	118.80 (18)	C9—C14—H14	120.00
C9—C10—C11	120.91 (18)	O3—C15—H15C	109.00
C10—C11—C12	119.94 (19)	O3—C15—H15B	109.00
C11—C12—C13	119.53 (19)	H15B—C15—H15C	109.00
O2—C12—C11	118.86 (18)	H15A—C15—H15B	109.00
O2—C12—C13	121.61 (17)	H15A—C15—H15C	109.00
O3—C13—C14	125.62 (18)	O3—C15—H15A	109.00
C15—O3—C13—C12	177.4 (2)	C4A—C5A—C6A—C1A	0.0 (3)
C15—O3—C13—C14	−4.5 (3)	N2—C8—C9—C10	−169.1 (2)
C7—N1—N2—C8	−173.59 (19)	N2—C8—C9—C14	15.8 (3)
N2—N1—C7—O1	10.0 (3)	C8—C9—C10—C11	−175.5 (2)
N2—N1—C7—C1A	−172.51 (17)	C14—C9—C10—C11	−0.3 (3)
N1—N2—C8—C9	−173.17 (18)	C8—C9—C14—C13	174.08 (19)
C6A—C1A—C2A—C3A	0.0 (3)	C10—C9—C14—C13	−1.1 (3)
C7—C1A—C2A—C3A	179.15 (19)	C9—C10—C11—C12	1.9 (3)
C2A—C1A—C6A—C5A	0.0 (3)	C10—C11—C12—O2	178.01 (19)
C7—C1A—C6A—C5A	−179.15 (17)	C10—C11—C12—C13	−2.1 (3)
C2A—C1A—C7—O1	−140.5 (2)	O2—C12—C13—O3	−1.2 (3)
C2A—C1A—C7—N1	42.0 (3)	O2—C12—C13—C14	−179.40 (18)
C6A—C1A—C7—O1	38.6 (3)	C11—C12—C13—O3	178.91 (18)
C6A—C1A—C7—N1	−138.89 (19)	C11—C12—C13—C14	0.7 (3)
C1A—C2A—C3A—C4A	0.0 (3)	O3—C13—C14—C9	−177.09 (19)
C2A—C3A—C4A—C5A	0.0 (3)	C12—C13—C14—C9	0.9 (3)
C3A—C4A—C5A—C6A	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	2.21	2.653 (2)	115
N1—H1···O1i	0.86	2.14	2.8633 (19)	142
O2—H2···O1ii	0.82	2.05	2.773 (2)	146
C2A—H2A···O1i	0.93	2.43	3.165 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	2.21	2.653 (2)	115
N1—H1⋯O1i	0.86	2.14	2.8633 (19)	142
O2—H2⋯O1ii	0.82	2.05	2.773 (2)	146
C2A—H2A⋯O1i	0.93	2.43	3.165 (2)	136

Symmetry codes: (i) ; (ii) .