N'-[(E)-2,3-Dihy-droxy-benzyl-idene]-2-meth-oxy-benzohydrazide.

The title compound, C15H14N2O4 adopts an E conformation about the azomethine double bond. Intra-molecular N-H⋯O and O-H⋯N hydrogen bonds generate S(6) rings and help to establish the molecular conformation. The dihedral angle between the benzene rings is 17.84 (10)°. In the crystal, mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds into a two-dimensional network with a herring-bone pattern arranged parallel to the bc plane.

Related literature

For applications and the biological activity of Schiff bases, see: Panneerselvam et al. (2009 ▶); Khan et al. (2009 ▶); Jarahpour et al. (2007 ▶). For related structures, see: Baharudin et al. (2012 ▶); Taha et al. (2012 ▶); Promdet et al. (2011 ▶).

Experimental

Crystal data

C15H14N2O4

M = 286.28

Orthorhombic,

a = 14.1479 (17) Å

b = 8.6567 (11) Å

c = 22.570 (3) Å

V = 2764.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 273 K

0.56 × 0.18 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.945, T max = 0.996

15288 measured reflections

2574 independent reflections

1658 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.03

2574 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042390/pv2594sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042390/pv2594Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042390/pv2594Isup3.cml

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

C15H14N2O4	F(000) = 1200
Mr = 286.28	Dx = 1.376 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1873 reflections
a = 14.1479 (17) Å	θ = 2.9–22.2°
b = 8.6567 (11) Å	µ = 0.10 mm−1
c = 22.570 (3) Å	T = 273 K
V = 2764.2 (6) Å3	Plate, colorles
Z = 8	0.56 × 0.18 × 0.04 mm

Bruker SMART APEX CCD area-detector diffractometer	2574 independent reflections
Radiation source: fine-focus sealed tube	1658 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scan	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→17
Tmin = 0.945, Tmax = 0.996	k = −10→10
15288 measured reflections	l = −27→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.050P)2 + 0.1101P] where P = (Fo2 + 2Fc2)/3
2574 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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
O1	0.14939 (10)	−0.02998 (18)	0.40701 (6)	0.0774 (5)
O2	0.43755 (10)	−0.00963 (18)	0.38297 (7)	0.0813 (5)
O3	−0.04853 (10)	0.35880 (19)	0.18114 (7)	0.0812 (5)
H3A	−0.0756 (18)	0.407 (3)	0.1500 (12)	0.124 (11)*
O4	0.04345 (10)	0.21110 (17)	0.26425 (7)	0.0705 (4)
H4A	0.0826 (17)	0.178 (3)	0.2896 (11)	0.106 (9)*
N1	0.26779 (14)	0.08816 (19)	0.35803 (7)	0.0591 (5)
H1A	0.3313 (16)	0.098 (3)	0.3523 (9)	0.087 (8)*
N2	0.20663 (11)	0.16136 (18)	0.31942 (7)	0.0569 (4)
C1	0.26911 (17)	−0.1677 (2)	0.48710 (9)	0.0752 (6)
H1B	0.2044	−0.1659	0.4943	0.090*
C2	0.3267 (2)	−0.2513 (3)	0.52416 (10)	0.0900 (7)
H2B	0.3011	−0.3049	0.5560	0.108*
C3	0.4220 (2)	−0.2550 (3)	0.51384 (11)	0.0924 (8)
H3B	0.4611	−0.3115	0.5389	0.111*
C4	0.46035 (17)	−0.1762 (3)	0.46702 (10)	0.0793 (7)
H4B	0.5252	−0.1801	0.4603	0.095*
C5	0.40271 (15)	−0.0908 (2)	0.42963 (9)	0.0628 (5)
C6	0.30501 (15)	−0.0859 (2)	0.43918 (8)	0.0575 (5)
C7	0.23441 (15)	−0.0071 (2)	0.40039 (8)	0.0576 (5)
C8	0.24524 (13)	0.2483 (2)	0.28070 (8)	0.0572 (5)
H8A	0.3106	0.2591	0.2809	0.069*
C9	0.19093 (12)	0.3307 (2)	0.23652 (8)	0.0498 (5)
C10	0.23670 (14)	0.4340 (2)	0.19876 (8)	0.0623 (5)
H10A	0.3015	0.4492	0.2026	0.075*
C11	0.18796 (15)	0.5134 (2)	0.15615 (9)	0.0661 (6)
H11A	0.2194	0.5829	0.1317	0.079*
C12	0.09193 (14)	0.4901 (2)	0.14946 (8)	0.0585 (5)
H12A	0.0588	0.5437	0.1204	0.070*
C13	0.04530 (13)	0.3880 (2)	0.18569 (8)	0.0532 (5)
C14	0.09401 (12)	0.3093 (2)	0.23002 (7)	0.0494 (5)
C15	0.53330 (16)	−0.0285 (3)	0.36517 (11)	0.0872 (7)
H15A	0.5444	0.0292	0.3295	0.131*
H15B	0.5458	−0.1359	0.3581	0.131*
H15C	0.5743	0.0086	0.3959	0.131*

	U11	U22	U33	U12	U13	U23
O1	0.0578 (10)	0.1019 (12)	0.0724 (10)	−0.0083 (8)	−0.0062 (7)	−0.0100 (8)
O2	0.0576 (10)	0.0926 (11)	0.0937 (11)	0.0069 (8)	0.0005 (8)	0.0279 (9)
O3	0.0449 (9)	0.1000 (12)	0.0987 (12)	−0.0024 (7)	−0.0091 (8)	0.0351 (10)
O4	0.0515 (9)	0.0821 (10)	0.0779 (10)	−0.0071 (7)	0.0010 (7)	0.0256 (8)
N1	0.0526 (11)	0.0636 (11)	0.0611 (10)	0.0055 (9)	−0.0122 (9)	−0.0064 (9)
N2	0.0563 (10)	0.0587 (10)	0.0558 (10)	0.0057 (8)	−0.0112 (8)	−0.0083 (8)
C1	0.0884 (17)	0.0784 (15)	0.0588 (13)	−0.0058 (13)	0.0001 (12)	−0.0060 (12)
C2	0.123 (2)	0.0840 (17)	0.0635 (15)	0.0011 (17)	−0.0016 (15)	0.0123 (13)
C3	0.120 (2)	0.0834 (17)	0.0741 (16)	0.0164 (17)	−0.0178 (15)	0.0069 (14)
C4	0.0828 (17)	0.0764 (15)	0.0787 (15)	0.0075 (12)	−0.0191 (13)	0.0026 (14)
C5	0.0692 (15)	0.0594 (12)	0.0597 (12)	−0.0002 (11)	−0.0112 (11)	−0.0026 (11)
C6	0.0672 (14)	0.0543 (11)	0.0512 (12)	−0.0023 (10)	−0.0087 (10)	−0.0108 (10)
C7	0.0594 (14)	0.0605 (12)	0.0528 (12)	−0.0033 (10)	−0.0059 (10)	−0.0153 (10)
C8	0.0467 (11)	0.0611 (11)	0.0638 (12)	−0.0008 (10)	−0.0078 (10)	−0.0143 (11)
C9	0.0457 (11)	0.0503 (10)	0.0533 (11)	−0.0015 (8)	0.0004 (8)	−0.0113 (9)
C10	0.0489 (12)	0.0679 (13)	0.0700 (13)	−0.0115 (10)	0.0054 (10)	−0.0082 (11)
C11	0.0723 (14)	0.0613 (13)	0.0648 (13)	−0.0153 (11)	0.0126 (11)	0.0012 (11)
C12	0.0644 (13)	0.0547 (11)	0.0565 (11)	0.0022 (10)	0.0021 (10)	0.0014 (10)
C13	0.0439 (11)	0.0541 (11)	0.0616 (12)	0.0017 (9)	0.0016 (9)	0.0011 (10)
C14	0.0465 (11)	0.0487 (10)	0.0531 (11)	−0.0023 (8)	0.0063 (9)	−0.0007 (9)
C15	0.0601 (15)	0.0902 (17)	0.1112 (19)	0.0038 (12)	0.0052 (13)	0.0059 (15)

O1—C7	1.228 (2)	C4—C5	1.387 (3)
O2—C5	1.359 (2)	C4—H4B	0.9300
O2—C15	1.422 (2)	C5—C6	1.400 (3)
O3—C13	1.355 (2)	C6—C7	1.493 (3)
O3—H3A	0.90 (3)	C8—C9	1.447 (2)
O4—C14	1.353 (2)	C8—H8A	0.9300
O4—H4A	0.85 (2)	C9—C14	1.392 (2)
N1—C7	1.348 (2)	C9—C10	1.395 (2)
N1—N2	1.382 (2)	C10—C11	1.368 (3)
N1—H1A	0.91 (2)	C10—H10A	0.9300
N2—C8	1.276 (2)	C11—C12	1.382 (3)
C1—C2	1.373 (3)	C11—H11A	0.9300
C1—C6	1.389 (3)	C12—C13	1.373 (2)
C1—H1B	0.9300	C12—H12A	0.9300
C2—C3	1.368 (3)	C13—C14	1.393 (2)
C2—H2B	0.9300	C15—H15A	0.9600
C3—C4	1.370 (3)	C15—H15B	0.9600
C3—H3B	0.9300	C15—H15C	0.9600
C5—O2—C15	120.34 (17)	N2—C8—C9	122.37 (17)
C13—O3—H3A	113.0 (17)	N2—C8—H8A	118.8
C14—O4—H4A	104.7 (17)	C9—C8—H8A	118.8
C7—N1—N2	120.55 (18)	C14—C9—C10	118.61 (17)
C7—N1—H1A	120.2 (14)	C14—C9—C8	122.01 (16)
N2—N1—H1A	119.1 (14)	C10—C9—C8	119.38 (17)
C8—N2—N1	115.74 (17)	C11—C10—C9	121.16 (19)
C2—C1—C6	121.7 (2)	C11—C10—H10A	119.4
C2—C1—H1B	119.1	C9—C10—H10A	119.4
C6—C1—H1B	119.1	C10—C11—C12	119.95 (18)
C3—C2—C1	119.5 (2)	C10—C11—H11A	120.0
C3—C2—H2B	120.2	C12—C11—H11A	120.0
C1—C2—H2B	120.2	C13—C12—C11	120.08 (18)
C2—C3—C4	120.7 (2)	C13—C12—H12A	120.0
C2—C3—H3B	119.7	C11—C12—H12A	120.0
C4—C3—H3B	119.7	O3—C13—C12	123.07 (17)
C3—C4—C5	120.1 (2)	O3—C13—C14	116.58 (17)
C3—C4—H4B	119.9	C12—C13—C14	120.34 (17)
C5—C4—H4B	119.9	O4—C14—C9	123.01 (16)
O2—C5—C4	122.3 (2)	O4—C14—C13	117.13 (16)
O2—C5—C6	117.50 (17)	C9—C14—C13	119.84 (16)
C4—C5—C6	120.2 (2)	O2—C15—H15A	109.5
C1—C6—C5	117.72 (19)	O2—C15—H15B	109.5
C1—C6—C7	116.4 (2)	H15A—C15—H15B	109.5
C5—C6—C7	125.77 (19)	O2—C15—H15C	109.5
O1—C7—N1	121.88 (19)	H15A—C15—H15C	109.5
O1—C7—C6	120.7 (2)	H15B—C15—H15C	109.5
N1—C7—C6	117.45 (19)
C7—N1—N2—C8	−179.58 (16)	C5—C6—C7—N1	−11.4 (3)
C6—C1—C2—C3	−0.2 (3)	N1—N2—C8—C9	178.90 (14)
C1—C2—C3—C4	0.0 (4)	N2—C8—C9—C14	−6.0 (3)
C2—C3—C4—C5	0.4 (4)	N2—C8—C9—C10	174.56 (16)
C15—O2—C5—C4	9.8 (3)	C14—C9—C10—C11	0.1 (3)
C15—O2—C5—C6	−170.20 (18)	C8—C9—C10—C11	179.55 (16)
C3—C4—C5—O2	179.4 (2)	C9—C10—C11—C12	−0.9 (3)
C3—C4—C5—C6	−0.6 (3)	C10—C11—C12—C13	0.3 (3)
C2—C1—C6—C5	−0.1 (3)	C11—C12—C13—O3	−179.38 (18)
C2—C1—C6—C7	176.70 (19)	C11—C12—C13—C14	1.1 (3)
O2—C5—C6—C1	−179.52 (17)	C10—C9—C14—O4	179.63 (16)
C4—C5—C6—C1	0.5 (3)	C8—C9—C14—O4	0.2 (3)
O2—C5—C6—C7	4.1 (3)	C10—C9—C14—C13	1.2 (2)
C4—C5—C6—C7	−175.94 (17)	C8—C9—C14—C13	−178.16 (16)
N2—N1—C7—O1	−1.4 (3)	O3—C13—C14—O4	0.1 (2)
N2—N1—C7—C6	178.09 (14)	C12—C13—C14—O4	179.65 (16)
C1—C6—C7—O1	−8.4 (3)	O3—C13—C14—C9	178.57 (16)
C5—C6—C7—O1	168.06 (18)	C12—C13—C14—C9	−1.9 (3)
C1—C6—C7—N1	172.13 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.91 (2)	1.90 (2)	2.608 (2)	133 (2)
O3—H3A···O1i	0.90 (3)	1.75 (3)	2.631 (2)	167 (2)
O4—H4A···N2	0.85 (2)	1.89 (2)	2.658 (2)	151 (2)
C8—H8A···O3ii	0.93	2.33	3.189 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.91 (2)	1.90 (2)	2.608 (2)	133 (2)
O3—H3A⋯O1i	0.90 (3)	1.75 (3)	2.631 (2)	167 (2)
O4—H4A⋯N2	0.85 (2)	1.89 (2)	2.658 (2)	151 (2)
C8—H8A⋯O3ii	0.93	2.33	3.189 (2)	153

Symmetry codes: (i) ; (ii) .