N'-(4-Hydroxy-benzyl-idene)-4-meth-oxybenzohydrazide.

The title compound, C(15)H(14)N(2)O(3), was prepared by the reaction of 4-hydroxy-benzaldehyde and 4-methoxy-benzohydrazide in methanol. The dihedral angle between the two benzene rings is 6.8 (1)°. The meth-oxy group is disordered over two orientations with occupancies of ca 0.63 and 0.37. In the major disorder component, the meth-oxy group is coplanar with the attached ring. In the crystal structure, the mol-ecules are linked into a three-dimensional framework by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the synthesis of Schiff bases, see: Akitsu & Einaga (2006 ▶); Butcher et al. (2005 ▶); Habibi et al. (2007 ▶); Pradeep (2005 ▶). For related Schiff base compounds, see: Wang et al. (2006 ▶); Wei et al. (2006 ▶, 2008a ▶,b ▶); Wei & Wang (2006 ▶); Zhu et al. (2007 ▶). For related structures, see: Odabaşoğlu et al. (2007 ▶); Yathirajan et al. (2007 ▶); Yehye et al. (2008 ▶).

Experimental

Crystal data

C15H14N2O3

M = 270.28

Orthorhombic,

a = 12.342 (2) Å

b = 7.854 (2) Å

c = 27.889 (3) Å

V = 2703.4 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 (2) K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.981

12214 measured reflections

2308 independent reflections

1591 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.135

S = 1.04

2308 reflections

201 parameters

26 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802360X/ci2639sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802360X/ci2639Isup2.hkl

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

C15H14N2O3	F000 = 1136
Mr = 270.28	Dx = 1.328 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2798 reflections
a = 12.342 (2) Å	θ = 2.4–24.1º
b = 7.854 (2) Å	µ = 0.09 mm−1
c = 27.889 (3) Å	T = 296 (2) K
V = 2703.4 (9) Å3	Cut from needle, colourless
Z = 8	0.23 × 0.20 × 0.20 mm

Bruker SMART 1000 CCD area-detector diffractometer	2308 independent reflections
Radiation source: fine-focus sealed tube	1591 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 296(2) K	θmax = 24.7º
ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −14→12
Tmin = 0.979, Tmax = 0.981	k = −9→9
12214 measured reflections	l = −32→29

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0514P)2 + 1.0313P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2308 reflections	Δρmax = 0.24 e Å−3
201 parameters	Δρmin = −0.24 e Å−3
26 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
O1	0.91965 (15)	−0.0226 (3)	0.86782 (6)	0.0813 (6)
H1	0.9779	0.0115	0.8782	0.122*
O2	0.61634 (13)	0.0498 (2)	0.59539 (5)	0.0645 (5)
N1	0.76203 (15)	0.1620 (2)	0.65728 (6)	0.0591 (5)
N2	0.74642 (15)	0.2399 (2)	0.61337 (6)	0.0599 (5)
H2A	0.7848	0.3265	0.6051	0.072*
C1	0.86057 (18)	0.1561 (3)	0.73055 (8)	0.0588 (6)
C2	0.7901 (2)	0.0470 (3)	0.75378 (8)	0.0700 (7)
H2	0.7271	0.0123	0.7383	0.084*
C3	0.8111 (2)	−0.0109 (4)	0.79911 (8)	0.0752 (8)
H3	0.7623	−0.0838	0.8141	0.090*
C4	0.90430 (19)	0.0382 (3)	0.82278 (8)	0.0596 (6)
C5	0.9763 (2)	0.1447 (3)	0.80018 (8)	0.0653 (6)
H5	1.0401	0.1768	0.8155	0.078*
C6	0.9535 (2)	0.2038 (3)	0.75471 (8)	0.0701 (7)
H6	1.0020	0.2777	0.7399	0.084*
C7	0.8374 (2)	0.2223 (3)	0.68288 (8)	0.0673 (7)
H7	0.8792	0.3113	0.6709	0.081*
C8	0.67021 (18)	0.1775 (3)	0.58398 (7)	0.0546 (6)
C9	0.65325 (19)	0.2623 (3)	0.53725 (8)	0.0605 (6)
C10	0.5570 (2)	0.2357 (4)	0.51343 (10)	0.0882 (9)
H10	0.5031	0.1693	0.5274	0.106*
C11	0.5400 (3)	0.3083 (4)	0.46835 (11)	0.1097 (12)
H11	0.4747	0.2901	0.4525	0.132*
C12	0.6183 (4)	0.4056 (4)	0.44727 (10)	0.1047 (12)
C13	0.7138 (3)	0.4305 (4)	0.47006 (9)	0.0938 (10)
H13	0.7678	0.4953	0.4556	0.113*
C14	0.7314 (2)	0.3606 (3)	0.51443 (8)	0.0735 (7)
H14	0.7973	0.3795	0.5297	0.088*
O3	0.6249 (4)	0.4882 (5)	0.40185 (13)	0.0866 (14)	0.630 (7)
C15	0.5326 (4)	0.4557 (6)	0.37318 (19)	0.0891 (18)	0.630 (7)
H15A	0.5397	0.5142	0.3431	0.134*	0.630 (7)
H15B	0.4689	0.4953	0.3895	0.134*	0.630 (7)
H15C	0.5266	0.3355	0.3675	0.134*	0.630 (7)
O3A	0.5470 (5)	0.4517 (9)	0.40930 (19)	0.092 (2)	0.370 (7)
C15A	0.6242 (10)	0.5249 (18)	0.3782 (4)	0.123 (5)	0.370 (7)
H15D	0.5889	0.5632	0.3495	0.185*	0.370 (7)
H15E	0.6781	0.4416	0.3702	0.185*	0.370 (7)
H15F	0.6582	0.6199	0.3938	0.185*	0.370 (7)

	U11	U22	U33	U12	U13	U23
O1	0.0866 (13)	0.0986 (14)	0.0586 (10)	−0.0037 (11)	−0.0139 (9)	0.0213 (10)
O2	0.0700 (10)	0.0642 (10)	0.0593 (9)	−0.0056 (9)	−0.0002 (8)	0.0010 (8)
N1	0.0716 (12)	0.0616 (12)	0.0440 (10)	−0.0018 (10)	−0.0069 (9)	0.0074 (9)
N2	0.0738 (12)	0.0587 (11)	0.0472 (10)	−0.0070 (10)	−0.0092 (10)	0.0078 (8)
C1	0.0698 (15)	0.0560 (13)	0.0507 (12)	−0.0037 (12)	−0.0085 (11)	0.0039 (11)
C2	0.0712 (16)	0.0746 (17)	0.0641 (14)	−0.0120 (14)	−0.0162 (12)	0.0100 (13)
C3	0.0751 (16)	0.0836 (19)	0.0668 (15)	−0.0157 (14)	−0.0104 (13)	0.0229 (14)
C4	0.0702 (15)	0.0594 (14)	0.0491 (13)	0.0066 (12)	−0.0070 (11)	0.0040 (11)
C5	0.0717 (15)	0.0651 (15)	0.0591 (14)	−0.0069 (13)	−0.0155 (12)	0.0025 (12)
C6	0.0786 (17)	0.0702 (17)	0.0615 (14)	−0.0191 (13)	−0.0114 (13)	0.0109 (12)
C7	0.0794 (17)	0.0673 (16)	0.0553 (14)	−0.0134 (13)	−0.0090 (12)	0.0096 (12)
C8	0.0612 (13)	0.0529 (13)	0.0498 (12)	0.0038 (11)	−0.0007 (11)	−0.0037 (10)
C9	0.0812 (17)	0.0507 (13)	0.0495 (12)	0.0051 (12)	−0.0145 (12)	−0.0050 (10)
C10	0.104 (2)	0.0766 (19)	0.0841 (19)	−0.0048 (16)	−0.0388 (17)	0.0022 (15)
C11	0.142 (3)	0.087 (2)	0.099 (2)	0.010 (2)	−0.075 (2)	−0.0072 (19)
C12	0.193 (4)	0.0605 (18)	0.0604 (18)	0.013 (2)	−0.040 (2)	−0.0018 (14)
C13	0.155 (3)	0.0744 (19)	0.0519 (15)	0.0010 (19)	−0.0118 (18)	0.0050 (13)
C14	0.103 (2)	0.0662 (16)	0.0512 (13)	−0.0025 (15)	−0.0111 (13)	0.0014 (12)
O3	0.105 (3)	0.090 (3)	0.064 (2)	−0.025 (2)	−0.024 (2)	0.0248 (19)
C15	0.115 (4)	0.090 (3)	0.063 (3)	0.003 (3)	−0.032 (3)	0.010 (2)
O3A	0.101 (5)	0.116 (5)	0.059 (4)	0.009 (4)	−0.019 (3)	0.019 (3)
C15A	0.137 (8)	0.137 (8)	0.095 (7)	−0.006 (6)	0.002 (7)	0.043 (6)

O1—C4	1.357 (2)	C9—C10	1.377 (3)
O1—H1	0.82	C9—C14	1.389 (3)
O2—C8	1.245 (3)	C10—C11	1.396 (4)
N1—C7	1.265 (3)	C10—H10	0.93
N1—N2	1.382 (2)	C11—C12	1.365 (5)
N2—C8	1.340 (3)	C11—H11	0.93
N2—H2A	0.86	C12—C13	1.354 (5)
C1—C6	1.382 (3)	C12—O3A	1.424 (6)
C1—C2	1.382 (3)	C12—O3	1.426 (4)
C1—C7	1.456 (3)	C13—C14	1.371 (3)
C2—C3	1.368 (3)	C13—H13	0.93
C2—H2	0.93	C14—H14	0.93
C3—C4	1.381 (3)	O3—C15	1.415 (5)
C3—H3	0.93	C15—H15A	0.96
C4—C5	1.373 (3)	C15—H15B	0.96
C5—C6	1.379 (3)	C15—H15C	0.96
C5—H5	0.93	O3A—C15A	1.412 (8)
C6—H6	0.93	C15A—H15D	0.96
C7—H7	0.93	C15A—H15E	0.96
C8—C9	1.479 (3)	C15A—H15F	0.96
C4—O1—H1	109.5	C9—C10—C11	120.1 (3)
C7—N1—N2	115.9 (2)	C9—C10—H10	120.0
C8—N2—N1	118.51 (19)	C11—C10—H10	120.0
C8—N2—H2A	120.7	C12—C11—C10	120.7 (3)
N1—N2—H2A	120.7	C12—C11—H11	119.6
C6—C1—C2	117.5 (2)	C10—C11—H11	119.6
C6—C1—C7	120.7 (2)	C13—C12—C11	119.7 (3)
C2—C1—C7	121.7 (2)	C13—C12—O3A	148.3 (4)
C3—C2—C1	121.3 (2)	C11—C12—O3A	91.4 (4)
C3—C2—H2	119.3	C13—C12—O3	107.6 (3)
C1—C2—H2	119.3	C11—C12—O3	132.7 (3)
C2—C3—C4	120.5 (2)	C12—C13—C14	120.2 (3)
C2—C3—H3	119.8	C12—C13—H13	119.9
C4—C3—H3	119.8	C14—C13—H13	119.9
O1—C4—C5	123.3 (2)	C13—C14—C9	121.8 (3)
O1—C4—C3	117.4 (2)	C13—C14—H14	119.1
C5—C4—C3	119.3 (2)	C9—C14—H14	119.1
C4—C5—C6	119.7 (2)	C15—O3—C12	111.9 (4)
C4—C5—H5	120.2	O3—C15—H15A	109.5
C6—C5—H5	120.2	O3—C15—H15B	109.5
C5—C6—C1	121.7 (2)	H15A—C15—H15B	109.5
C5—C6—H6	119.1	O3—C15—H15C	109.5
C1—C6—H6	119.1	H15A—C15—H15C	109.5
N1—C7—C1	121.7 (2)	H15B—C15—H15C	109.5
N1—C7—H7	119.1	C15A—O3A—C12	98.2 (8)
C1—C7—H7	119.1	O3A—C15A—H15D	109.5
O2—C8—N2	120.9 (2)	O3A—C15A—H15E	109.5
O2—C8—C9	120.8 (2)	H15D—C15A—H15E	109.5
N2—C8—C9	118.3 (2)	O3A—C15A—H15F	109.5
C10—C9—C14	117.5 (2)	H15D—C15A—H15F	109.5
C10—C9—C8	118.6 (2)	H15E—C15A—H15F	109.5
C14—C9—C8	123.8 (2)
C7—N1—N2—C8	177.7 (2)	N2—C8—C9—C14	23.2 (3)
C6—C1—C2—C3	0.4 (4)	C14—C9—C10—C11	−0.9 (4)
C7—C1—C2—C3	−178.2 (2)	C8—C9—C10—C11	−177.4 (2)
C1—C2—C3—C4	−0.3 (4)	C9—C10—C11—C12	0.2 (5)
C2—C3—C4—O1	179.4 (2)	C10—C11—C12—C13	0.8 (5)
C2—C3—C4—C5	−0.6 (4)	C10—C11—C12—O3A	−173.0 (4)
O1—C4—C5—C6	−178.6 (2)	C10—C11—C12—O3	177.2 (4)
C3—C4—C5—C6	1.4 (4)	C11—C12—C13—C14	−1.0 (5)
C4—C5—C6—C1	−1.3 (4)	O3A—C12—C13—C14	167.1 (6)
C2—C1—C6—C5	0.4 (4)	O3—C12—C13—C14	−178.3 (3)
C7—C1—C6—C5	179.0 (2)	C12—C13—C14—C9	0.3 (4)
N2—N1—C7—C1	178.0 (2)	C10—C9—C14—C13	0.6 (4)
C6—C1—C7—N1	169.3 (2)	C8—C9—C14—C13	176.9 (2)
C2—C1—C7—N1	−12.1 (4)	C13—C12—O3—C15	174.2 (4)
N1—N2—C8—O2	−1.7 (3)	C11—C12—O3—C15	−2.5 (7)
N1—N2—C8—C9	179.47 (18)	O3A—C12—O3—C15	−17.1 (5)
O2—C8—C9—C10	20.6 (3)	C13—C12—O3A—C15A	22.4 (11)
N2—C8—C9—C10	−160.5 (2)	C11—C12—O3A—C15A	−167.9 (7)
O2—C8—C9—C14	−155.7 (2)	O3—C12—O3A—C15A	1.4 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86	2.15	3.007 (3)	172
O1—H1···O2ii	0.82	1.88	2.696 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.15	3.007 (3)	172
O1—H1⋯O2ii	0.82	1.88	2.696 (2)	170

Symmetry codes: (i) ; (ii) .