(E)-N'-(2,3-Dihy-droxy-benzyl-idene)-4-meth-oxy-benzohydrazide.

The mol-ecule of the title benzohydrazide derivative, C(15)H(14)N(2)O(4), is twisted and exists in a trans conformation with respect to the C=N double bond. The dihedral angle between the benzene rings is 56.86 (9)° and the C atom of the meth-oxy group deviates slightly [C-O-C-C = -10.4 (3)°] from its attached benzene ring. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by N-H⋯O and bifurcated N-H⋯(O,O) hydrogen bonds, as well as weak C-H⋯O inter-actions, into two-dimensional networks lying parallel to the bc plane. A weak C-H⋯π inter-action also occurs.

Related literature

For background to benzohydrides and related structures, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶). For related structures, see: Han & Zhao (2010 ▶); Li & Ban (2009 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H14N2O4

M = 286.28

Monoclinic,

a = 11.6242 (15) Å

b = 9.7516 (13) Å

c = 12.6465 (16) Å

β = 96.409 (2)°

V = 1424.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 297 K

0.34 × 0.22 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.967, T max = 0.992

13930 measured reflections

3768 independent reflections

2203 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.136

S = 1.02

3768 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045740/hb6485sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045740/hb6485Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045740/hb6485Isup3.cml

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

C15H14N2O4	F(000) = 600
Mr = 286.28	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Melting point = 502–503 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.6242 (15) Å	Cell parameters from 3768 reflections
b = 9.7516 (13) Å	θ = 2.6–29.0°
c = 12.6465 (16) Å	µ = 0.10 mm−1
β = 96.409 (2)°	T = 297 K
V = 1424.6 (3) Å3	Block, yellow
Z = 4	0.34 × 0.22 × 0.08 mm

Bruker SMART APEXII CCD diffractometer	3768 independent reflections
Radiation source: fine-focus sealed tube	2203 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: 8.33 pixels mm-1	θmax = 29.0°, θmin = 2.6°
ω scans	h = −14→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→12
Tmin = 0.967, Tmax = 0.992	l = −17→17
13930 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.2931P] where P = (Fo2 + 2Fc2)/3
3768 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.18 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
O1	0.76198 (12)	0.03025 (16)	1.01358 (9)	0.0644 (4)
O2	0.52798 (13)	−0.17500 (15)	0.56417 (11)	0.0716 (4)
O3	0.95302 (12)	0.31125 (15)	1.18591 (10)	0.0573 (4)
H1O3	0.919 (2)	0.266 (3)	1.131 (2)	0.105 (9)*
O4	1.07704 (14)	0.45742 (15)	1.33066 (10)	0.0655 (4)
H1O4	1.134 (2)	0.491 (2)	1.380 (2)	0.092 (8)*
N1	0.86300 (14)	0.15397 (15)	0.90461 (11)	0.0472 (4)
H1N1	0.8895 (16)	0.1593 (18)	0.8436 (15)	0.050 (5)*
N2	0.92453 (13)	0.21946 (15)	0.98936 (10)	0.0457 (4)
C1	0.71751 (15)	−0.00089 (18)	0.82727 (13)	0.0432 (4)
C2	0.68810 (17)	−0.13814 (19)	0.82957 (15)	0.0574 (5)
H2A	0.7107	−0.1896	0.8903	0.069*
C3	0.62568 (18)	−0.2001 (2)	0.74317 (17)	0.0621 (5)
H3A	0.6080	−0.2930	0.7453	0.075*
C4	0.58959 (16)	−0.12397 (19)	0.65375 (14)	0.0516 (5)
C5	0.61520 (18)	0.0146 (2)	0.65158 (14)	0.0548 (5)
H5A	0.5883	0.0672	0.5926	0.066*
C6	0.68036 (17)	0.07452 (19)	0.73656 (13)	0.0514 (5)
H6A	0.6999	0.1668	0.7334	0.062*
C7	0.78258 (15)	0.06096 (18)	0.92317 (12)	0.0445 (4)
C8	1.01140 (16)	0.29144 (17)	0.96886 (13)	0.0451 (4)
H8A	1.0311	0.2950	0.8996	0.054*
C9	1.07959 (15)	0.36759 (16)	1.05231 (12)	0.0417 (4)
C10	1.04835 (15)	0.37551 (17)	1.15543 (13)	0.0426 (4)
C11	1.11564 (16)	0.45196 (17)	1.23312 (13)	0.0464 (4)
C12	1.21434 (17)	0.51668 (18)	1.20748 (15)	0.0525 (5)
H12A	1.2599	0.5662	1.2593	0.063*
C13	1.24602 (18)	0.50867 (19)	1.10575 (16)	0.0569 (5)
H13A	1.3128	0.5527	1.0894	0.068*
C14	1.17932 (17)	0.43587 (18)	1.02824 (14)	0.0512 (5)
H14A	1.2006	0.4321	0.9596	0.061*
C15	0.5152 (2)	−0.3199 (2)	0.5548 (2)	0.0828 (7)
H15A	0.4773	−0.3422	0.4856	0.124*
H15B	0.4697	−0.3528	0.6083	0.124*
H15C	0.5902	−0.3624	0.5642	0.124*

	U11	U22	U33	U12	U13	U23
O1	0.0620 (9)	0.0923 (11)	0.0369 (6)	−0.0148 (8)	−0.0038 (6)	0.0134 (6)
O2	0.0770 (11)	0.0673 (9)	0.0646 (9)	−0.0017 (8)	−0.0194 (7)	−0.0185 (7)
O3	0.0611 (9)	0.0729 (9)	0.0388 (6)	−0.0241 (7)	0.0097 (6)	−0.0122 (6)
O4	0.0805 (11)	0.0773 (10)	0.0381 (7)	−0.0266 (8)	0.0033 (7)	−0.0101 (6)
N1	0.0545 (10)	0.0569 (9)	0.0299 (7)	−0.0064 (7)	0.0029 (6)	−0.0053 (6)
N2	0.0505 (9)	0.0523 (8)	0.0330 (7)	−0.0019 (7)	−0.0011 (6)	−0.0064 (6)
C1	0.0434 (10)	0.0478 (9)	0.0371 (8)	0.0021 (8)	−0.0017 (7)	0.0014 (7)
C2	0.0612 (13)	0.0513 (11)	0.0557 (11)	0.0040 (9)	−0.0112 (9)	0.0120 (8)
C3	0.0671 (14)	0.0444 (10)	0.0707 (12)	−0.0024 (9)	−0.0107 (10)	0.0010 (9)
C4	0.0473 (11)	0.0560 (11)	0.0494 (10)	0.0029 (9)	−0.0036 (8)	−0.0099 (8)
C5	0.0683 (13)	0.0549 (11)	0.0381 (9)	0.0039 (9)	−0.0073 (8)	0.0027 (8)
C6	0.0685 (13)	0.0455 (10)	0.0381 (8)	−0.0016 (9)	−0.0036 (8)	0.0023 (7)
C7	0.0441 (10)	0.0522 (10)	0.0356 (8)	0.0049 (8)	−0.0025 (7)	0.0041 (7)
C8	0.0537 (11)	0.0469 (9)	0.0348 (8)	0.0037 (8)	0.0054 (7)	−0.0022 (7)
C9	0.0448 (10)	0.0406 (9)	0.0391 (8)	0.0025 (7)	0.0021 (7)	0.0012 (7)
C10	0.0448 (10)	0.0431 (9)	0.0392 (8)	−0.0026 (7)	0.0013 (7)	0.0008 (7)
C11	0.0555 (12)	0.0435 (9)	0.0383 (8)	−0.0038 (8)	−0.0029 (8)	0.0006 (7)
C12	0.0561 (12)	0.0438 (10)	0.0545 (10)	−0.0082 (9)	−0.0080 (9)	0.0023 (8)
C13	0.0530 (12)	0.0523 (11)	0.0654 (12)	−0.0090 (9)	0.0066 (9)	0.0067 (9)
C14	0.0554 (12)	0.0507 (10)	0.0487 (10)	−0.0017 (9)	0.0110 (9)	0.0045 (8)
C15	0.0923 (19)	0.0771 (16)	0.0788 (15)	−0.0244 (14)	0.0085 (13)	−0.0273 (13)

O1—C7	1.231 (2)	C4—C5	1.385 (3)
O2—C4	1.365 (2)	C5—C6	1.374 (2)
O2—C15	1.424 (3)	C5—H5A	0.9300
O3—C10	1.365 (2)	C6—H6A	0.9300
O3—H1O3	0.88 (3)	C8—C9	1.451 (2)
O4—C11	1.360 (2)	C8—H8A	0.9300
O4—H1O4	0.91 (3)	C9—C10	1.394 (2)
N1—C7	1.342 (2)	C9—C14	1.400 (2)
N1—N2	1.3773 (18)	C10—C11	1.401 (2)
N1—H1N1	0.863 (19)	C11—C12	1.379 (3)
N2—C8	1.280 (2)	C12—C13	1.379 (3)
C1—C2	1.382 (3)	C12—H12A	0.9300
C1—C6	1.390 (2)	C13—C14	1.377 (3)
C1—C7	1.484 (2)	C13—H13A	0.9300
C2—C3	1.382 (3)	C14—H14A	0.9300
C2—H2A	0.9300	C15—H15A	0.9600
C3—C4	1.379 (3)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600
C4—O2—C15	118.09 (17)	N2—C8—C9	120.83 (15)
C10—O3—H1O3	108.7 (17)	N2—C8—H8A	119.6
C11—O4—H1O4	110.3 (16)	C9—C8—H8A	119.6
C7—N1—N2	119.26 (14)	C10—C9—C14	119.05 (16)
C7—N1—H1N1	121.5 (12)	C10—C9—C8	122.03 (16)
N2—N1—H1N1	117.5 (12)	C14—C9—C8	118.92 (15)
C8—N2—N1	116.72 (14)	O3—C10—C9	122.88 (15)
C2—C1—C6	118.34 (16)	O3—C10—C11	116.98 (15)
C2—C1—C7	118.75 (15)	C9—C10—C11	120.15 (16)
C6—C1—C7	122.85 (16)	O4—C11—C12	124.23 (16)
C3—C2—C1	121.08 (17)	O4—C11—C10	116.24 (16)
C3—C2—H2A	119.5	C12—C11—C10	119.52 (16)
C1—C2—H2A	119.5	C11—C12—C13	120.59 (17)
C4—C3—C2	119.86 (18)	C11—C12—H12A	119.7
C4—C3—H3A	120.1	C13—C12—H12A	119.7
C2—C3—H3A	120.1	C14—C13—C12	120.36 (18)
O2—C4—C3	124.61 (18)	C14—C13—H13A	119.8
O2—C4—C5	115.69 (17)	C12—C13—H13A	119.8
C3—C4—C5	119.71 (17)	C13—C14—C9	120.31 (17)
C6—C5—C4	120.02 (17)	C13—C14—H14A	119.8
C6—C5—H5A	120.0	C9—C14—H14A	119.8
C4—C5—H5A	120.0	O2—C15—H15A	109.5
C5—C6—C1	120.93 (17)	O2—C15—H15B	109.5
C5—C6—H6A	119.5	H15A—C15—H15B	109.5
C1—C6—H6A	119.5	O2—C15—H15C	109.5
O1—C7—N1	122.57 (16)	H15A—C15—H15C	109.5
O1—C7—C1	121.74 (17)	H15B—C15—H15C	109.5
N1—C7—C1	115.67 (14)
C7—N1—N2—C8	169.90 (16)	C6—C1—C7—N1	−40.2 (2)
C6—C1—C2—C3	1.5 (3)	N1—N2—C8—C9	178.17 (15)
C7—C1—C2—C3	178.77 (19)	N2—C8—C9—C10	−5.6 (3)
C1—C2—C3—C4	−1.4 (3)	N2—C8—C9—C14	174.85 (16)
C15—O2—C4—C3	−10.4 (3)	C14—C9—C10—O3	−179.49 (16)
C15—O2—C4—C5	170.0 (2)	C8—C9—C10—O3	1.0 (3)
C2—C3—C4—O2	179.78 (19)	C14—C9—C10—C11	0.6 (3)
C2—C3—C4—C5	−0.6 (3)	C8—C9—C10—C11	−178.97 (16)
O2—C4—C5—C6	−177.74 (19)	O3—C10—C11—O4	−1.8 (2)
C3—C4—C5—C6	2.6 (3)	C9—C10—C11—O4	178.15 (16)
C4—C5—C6—C1	−2.6 (3)	O3—C10—C11—C12	178.61 (16)
C2—C1—C6—C5	0.5 (3)	C9—C10—C11—C12	−1.5 (3)
C7—C1—C6—C5	−176.62 (18)	O4—C11—C12—C13	−178.43 (18)
N2—N1—C7—O1	−0.8 (3)	C10—C11—C12—C13	1.1 (3)
N2—N1—C7—C1	177.88 (14)	C11—C12—C13—C14	0.0 (3)
C2—C1—C7—O1	−38.7 (3)	C12—C13—C14—C9	−0.9 (3)
C6—C1—C7—O1	138.5 (2)	C10—C9—C14—C13	0.6 (3)
C2—C1—C7—N1	142.68 (18)	C8—C9—C14—C13	−179.82 (17)

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N2	0.88 (3)	1.86 (3)	2.6279 (18)	146 (2)
O4—H1O4···O1i	0.92 (2)	1.75 (2)	2.6577 (19)	170 (2)
N1—H1N1···O3ii	0.864 (19)	2.221 (19)	3.083 (2)	175.8 (17)
N1—H1N1···O4ii	0.864 (19)	2.481 (19)	2.961 (2)	115.8 (15)
C5—H5A···O2iii	0.93	2.50	3.413 (2)	166
C2—H2A···Cg1iv	0.93	3.00	3.539 (2)	119

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯N2	0.88 (3)	1.86 (3)	2.6279 (18)	146 (2)
O4—H1O4⋯O1i	0.92 (2)	1.75 (2)	2.6577 (19)	170 (2)
N1—H1N1⋯O3ii	0.864 (19)	2.221 (19)	3.083 (2)	175.8 (17)
N1—H1N1⋯O4ii	0.864 (19)	2.481 (19)	2.961 (2)	115.8 (15)
C5—H5A⋯O2iii	0.93	2.50	3.413 (2)	166
C2—H2A⋯Cg1iv	0.93	3.00	3.539 (2)	119

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .