4-Hydr-oxy-N'-(4-methoxy-benzyl-idene)benzohydrazide.

The title compound, C(15)H(14)N(2)O(3), was synthesized by the reaction of 4-methoxy-benzaldehyde with 4-hydroxy-benzohydrazide in methanol. The mol-ecule adopts an E configuration about the C=N bond. The two benzene rings make a dihedral angle of 46.6 (2)°. In the crystal structure, mol-ecules are linked into a two-dimensional network parallel to (001) through O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the anti­bacterial activity of hydrazone compounds, see: Cukurovali et al. (2006 ▶). For crystal structures of hydrazone compounds, see: Abdul Alhadi et al. (2009 ▶); Mohd Lair et al. (2009 ▶); Cao & Lu (2009 ▶); Qu & Cao (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14N2O3

M = 270.28

Orthorhombic,

a = 11.947 (2) Å

b = 7.555 (1) Å

c = 29.452 (2) Å

V = 2658.3 (6) Å3

Z = 8

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

15205 measured reflections

2897 independent reflections

2030 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.04

2897 reflections

187 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.15 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/S1600536809030621/ci2875sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030621/ci2875Isup2.hkl

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

C15H14N2O3	F(000) = 1136
Mr = 270.28	Dx = 1.351 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2853 reflections
a = 11.947 (2) Å	θ = 2.6–25.0°
b = 7.555 (1) Å	µ = 0.10 mm−1
c = 29.452 (2) Å	T = 298 K
V = 2658.3 (6) Å3	Block, colourless
Z = 8	0.20 × 0.20 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	2897 independent reflections
Radiation source: fine-focus sealed tube	2030 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 27.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→15
Tmin = 0.981, Tmax = 0.984	k = −9→9
15205 measured reflections	l = −33→37

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0418P)2 + 0.5702P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2897 reflections	Δρmax = 0.18 e Å−3
187 parameters	Δρmin = −0.15 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (7)

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	0.77001 (10)	0.20495 (17)	0.58903 (4)	0.0428 (3)
N2	0.75665 (11)	0.28526 (17)	0.63096 (4)	0.0427 (3)
O1	0.93859 (13)	0.00418 (19)	0.39100 (4)	0.0755 (4)
O2	0.60541 (8)	0.11510 (14)	0.64634 (3)	0.0460 (3)
O3	0.61014 (9)	0.54911 (17)	0.82831 (3)	0.0535 (3)
H3	0.5439	0.5709	0.8329	0.080*
C1	0.86784 (12)	0.2014 (2)	0.51899 (5)	0.0407 (4)
C2	0.79314 (13)	0.0874 (2)	0.49804 (5)	0.0487 (4)
H2	0.7279	0.0556	0.5132	0.058*
C3	0.81269 (14)	0.0203 (2)	0.45558 (5)	0.0535 (4)
H3A	0.7616	−0.0568	0.4423	0.064*
C4	0.90936 (15)	0.0683 (2)	0.43253 (5)	0.0518 (4)
C5	0.98315 (15)	0.1872 (2)	0.45215 (6)	0.0567 (5)
H5	1.0465	0.2232	0.4363	0.068*
C6	0.96304 (14)	0.2522 (2)	0.49499 (6)	0.0498 (4)
H6	1.0135	0.3308	0.5081	0.060*
C7	0.8819 (2)	−0.1482 (3)	0.37488 (7)	0.0800 (6)
H7A	0.8849	−0.2396	0.3975	0.120*
H7B	0.9171	−0.1893	0.3476	0.120*
H7C	0.8052	−0.1190	0.3687	0.120*
C8	0.84886 (12)	0.2682 (2)	0.56475 (5)	0.0426 (4)
H8	0.8944	0.3574	0.5763	0.051*
C9	0.67022 (11)	0.23670 (19)	0.65719 (5)	0.0363 (3)
C10	0.65784 (11)	0.33283 (19)	0.70077 (5)	0.0359 (3)
C11	0.74372 (12)	0.3390 (2)	0.73227 (5)	0.0418 (4)
H11	0.8139	0.2948	0.7247	0.050*
C12	0.72609 (12)	0.4102 (2)	0.77481 (5)	0.0460 (4)
H12	0.7839	0.4114	0.7960	0.055*
C13	0.62246 (12)	0.4800 (2)	0.78614 (5)	0.0391 (4)
C14	0.53678 (12)	0.4772 (2)	0.75443 (5)	0.0414 (4)
H14	0.4675	0.5261	0.7615	0.050*
C15	0.55430 (12)	0.4021 (2)	0.71250 (5)	0.0422 (4)
H15	0.4958	0.3977	0.6917	0.051*
H2A	0.8008 (14)	0.3787 (19)	0.6374 (6)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0453 (7)	0.0455 (8)	0.0375 (7)	−0.0003 (6)	0.0089 (6)	−0.0040 (6)
N2	0.0450 (7)	0.0437 (7)	0.0393 (7)	−0.0044 (6)	0.0098 (6)	−0.0066 (6)
O1	0.1010 (11)	0.0751 (10)	0.0503 (8)	−0.0109 (8)	0.0234 (7)	−0.0152 (6)
O2	0.0436 (6)	0.0499 (7)	0.0447 (6)	−0.0074 (5)	0.0081 (5)	−0.0078 (5)
O3	0.0464 (6)	0.0737 (8)	0.0404 (6)	0.0078 (6)	0.0045 (5)	−0.0117 (5)
C1	0.0425 (8)	0.0401 (8)	0.0396 (8)	0.0018 (7)	0.0081 (6)	0.0033 (6)
C2	0.0471 (9)	0.0513 (10)	0.0478 (9)	−0.0039 (8)	0.0096 (7)	0.0015 (7)
C3	0.0601 (11)	0.0542 (10)	0.0464 (9)	−0.0064 (8)	0.0015 (8)	−0.0035 (8)
C4	0.0642 (11)	0.0501 (10)	0.0412 (9)	0.0023 (9)	0.0109 (8)	0.0001 (7)
C5	0.0597 (10)	0.0585 (11)	0.0519 (10)	−0.0062 (9)	0.0217 (8)	−0.0006 (8)
C6	0.0501 (9)	0.0482 (9)	0.0512 (9)	−0.0069 (8)	0.0115 (7)	−0.0013 (7)
C7	0.1133 (17)	0.0747 (14)	0.0520 (11)	−0.0059 (14)	0.0008 (11)	−0.0156 (10)
C8	0.0411 (8)	0.0418 (9)	0.0449 (8)	−0.0003 (7)	0.0058 (7)	0.0002 (7)
C9	0.0356 (7)	0.0365 (8)	0.0369 (8)	0.0022 (6)	0.0015 (6)	0.0018 (6)
C10	0.0359 (7)	0.0355 (8)	0.0363 (7)	−0.0006 (6)	0.0051 (6)	0.0011 (6)
C11	0.0320 (7)	0.0495 (9)	0.0438 (8)	0.0056 (7)	0.0050 (6)	−0.0003 (7)
C12	0.0364 (8)	0.0616 (11)	0.0401 (8)	0.0057 (7)	−0.0030 (6)	−0.0039 (7)
C13	0.0401 (8)	0.0411 (8)	0.0360 (8)	0.0000 (7)	0.0059 (6)	0.0005 (6)
C14	0.0319 (7)	0.0442 (9)	0.0480 (9)	0.0034 (6)	0.0056 (6)	−0.0051 (7)
C15	0.0339 (8)	0.0477 (9)	0.0449 (8)	0.0021 (7)	−0.0019 (6)	−0.0039 (7)

N1—C8	1.2758 (18)	C5—H5	0.93
N1—N2	1.3850 (16)	C6—H6	0.93
N2—C9	1.3408 (18)	C7—H7A	0.96
N2—H2A	0.901 (9)	C7—H7B	0.96
O1—C4	1.3610 (19)	C7—H7C	0.96
O1—C7	1.418 (2)	C8—H8	0.93
O2—C9	1.2431 (17)	C9—C10	1.4822 (19)
O3—C13	1.3554 (17)	C10—C11	1.3841 (19)
O3—H3	0.82	C10—C15	1.3868 (19)
C1—C2	1.385 (2)	C11—C12	1.3797 (19)
C1—C6	1.393 (2)	C11—H11	0.93
C1—C8	1.457 (2)	C12—C13	1.386 (2)
C2—C3	1.370 (2)	C12—H12	0.93
C2—H2	0.93	C13—C14	1.386 (2)
C3—C4	1.388 (2)	C14—C15	1.375 (2)
C3—H3A	0.93	C14—H14	0.93
C4—C5	1.385 (2)	C15—H15	0.93
C5—C6	1.375 (2)
C8—N1—N2	114.89 (13)	O1—C7—H7C	109.5
C9—N2—N1	118.86 (13)	H7A—C7—H7C	109.5
C9—N2—H2A	123.0 (12)	H7B—C7—H7C	109.5
N1—N2—H2A	117.5 (12)	N1—C8—C1	120.25 (14)
C4—O1—C7	117.85 (15)	N1—C8—H8	119.9
C13—O3—H3	109.5	C1—C8—H8	119.9
C2—C1—C6	118.11 (14)	O2—C9—N2	122.26 (13)
C2—C1—C8	121.81 (13)	O2—C9—C10	121.50 (12)
C6—C1—C8	120.08 (14)	N2—C9—C10	116.22 (13)
C3—C2—C1	121.80 (15)	C11—C10—C15	118.78 (13)
C3—C2—H2	119.1	C11—C10—C9	121.54 (12)
C1—C2—H2	119.1	C15—C10—C9	119.31 (13)
C2—C3—C4	119.46 (16)	C12—C11—C10	120.58 (13)
C2—C3—H3A	120.3	C12—C11—H11	119.7
C4—C3—H3A	120.3	C10—C11—H11	119.7
O1—C4—C5	116.26 (15)	C11—C12—C13	120.21 (13)
O1—C4—C3	124.07 (16)	C11—C12—H12	119.9
C5—C4—C3	119.67 (15)	C13—C12—H12	119.9
C6—C5—C4	120.22 (15)	O3—C13—C14	122.91 (13)
C6—C5—H5	119.9	O3—C13—C12	117.64 (13)
C4—C5—H5	119.9	C14—C13—C12	119.44 (13)
C5—C6—C1	120.67 (16)	C15—C14—C13	119.94 (13)
C5—C6—H6	119.7	C15—C14—H14	120.0
C1—C6—H6	119.7	C13—C14—H14	120.0
O1—C7—H7A	109.5	C14—C15—C10	121.01 (13)
O1—C7—H7B	109.5	C14—C15—H15	119.5
H7A—C7—H7B	109.5	C10—C15—H15	119.5

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2i	0.82	1.91	2.7271 (15)	171
N2—H2A···O2ii	0.90 (1)	2.12 (1)	3.0216 (17)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2i	0.82	1.91	2.7271 (15)	171
N2—H2A⋯O2ii	0.90 (1)	2.12 (1)	3.0216 (17)	173 (2)

Symmetry codes: (i) ; (ii) .