(E)-N'-(3-Eth-oxy-4-hy-droxy-benzyl-idene)-4-meth-oxy-benzohydrazide.

In the mol-ecule of the title benzohydrazide derivative, C(17)H(18)N(2)O(4), the dihedral angle between the benzene rings is 6.86 (11)°. The meth-oxy group of the 4-meth-oxy-phenyl fragment deviates slightly [C(methyl)-O-C-C = 10.0 (4)°] with respect to the benzene ring, whereas the eth-oxy group of the 3-eth-oxy-4-hy-droxy-phenyl fragment is is almost coplanar [C-O-C-C(methyl) = 178.5 (2)°]. In the crystal, mol-ecules are linked by N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds into a two-dimensional network parallel to the ab plane. C-H⋯π inter-actions and C⋯O [2.980 (3) Å] short contacts are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶); Promdet et al. (2011 ▶). For background and applications to benzohydrazide derivatives, see: Bedia et al. (2006 ▶); Loncle et al. (2004 ▶); Raj et al. (2007 ▶).

Experimental

Crystal data

C17H18N2O4

M = 314.33

Orthorhombic,

a = 5.0607 (9) Å

b = 11.086 (2) Å

c = 27.629 (5) Å

V = 1550.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 297 K

0.56 × 0.10 × 0.07 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.948, T max = 0.993

10252 measured reflections

2637 independent reflections

1921 reflections with I > 2σ(I)

R int = 0.100

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.154

S = 1.04

2637 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.35 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/S1600536812007374/rz2713sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007374/rz2713Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007374/rz2713Isup3.cml

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

C17H18N2O4	Dx = 1.347 Mg m−3
Mr = 314.33	Melting point = 486–488 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2637 reflections
a = 5.0607 (9) Å	θ = 1.5–30.1°
b = 11.086 (2) Å	µ = 0.10 mm−1
c = 27.629 (5) Å	T = 297 K
V = 1550.1 (5) Å3	Needle, colorless
Z = 4	0.56 × 0.10 × 0.07 mm
F(000) = 664

Bruker APEX DUO CCD area-detector diffractometer	2637 independent reflections
Radiation source: sealed tube	1921 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.100
φ and ω scans	θmax = 30.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.948, Tmax = 0.993	k = −15→15
10252 measured reflections	l = −38→29

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0865P)2 + 0.0494P] where P = (Fo2 + 2Fc2)/3
2637 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.35 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	0.7066 (4)	0.1645 (2)	0.40465 (7)	0.0575 (5)
O2	0.2255 (5)	−0.16566 (19)	0.57022 (7)	0.0623 (6)
O3	0.5434 (4)	0.52128 (16)	0.19944 (6)	0.0450 (4)
O4	0.2111 (4)	0.70975 (15)	0.20065 (7)	0.0499 (5)
H1O4	0.2354	0.6755	0.1747	0.075*
N1	0.2812 (5)	0.2287 (2)	0.40261 (8)	0.0445 (5)
H1N1	0.1137	0.2022	0.4041	0.067*
N2	0.3378 (5)	0.30448 (19)	0.36411 (8)	0.0465 (5)
C1	0.4040 (5)	0.0790 (2)	0.46083 (9)	0.0390 (5)
C2	0.5413 (6)	−0.0295 (3)	0.46673 (9)	0.0469 (6)
H2A	0.6794	−0.0482	0.4458	0.056*
C3	0.4754 (7)	−0.1084 (2)	0.50282 (9)	0.0518 (7)
H3A	0.5660	−0.1810	0.5057	0.062*
C4	0.2741 (6)	−0.0809 (2)	0.53512 (9)	0.0460 (6)
C5	0.1377 (7)	0.0268 (3)	0.53087 (10)	0.0516 (7)
H5A	0.0048	0.0464	0.5527	0.062*
C6	0.2019 (6)	0.1050 (2)	0.49356 (10)	0.0471 (6)
H6A	0.1079	0.1766	0.4902	0.057*
C7	0.4803 (5)	0.1604 (2)	0.42070 (9)	0.0415 (5)
C8	0.1489 (6)	0.3765 (2)	0.35246 (9)	0.0439 (6)
H8A	−0.0064	0.3750	0.3705	0.053*
C9	0.1701 (5)	0.4600 (2)	0.31206 (9)	0.0394 (5)
C10	0.3601 (5)	0.4457 (2)	0.27571 (9)	0.0387 (5)
H10A	0.4775	0.3812	0.2770	0.046*
C11	0.3739 (5)	0.5275 (2)	0.23787 (8)	0.0363 (5)
C12	0.2013 (5)	0.6265 (2)	0.23665 (9)	0.0374 (5)
C13	0.0117 (6)	0.6400 (2)	0.27242 (9)	0.0438 (6)
H13A	−0.1046	0.7049	0.2714	0.053*
C14	−0.0044 (6)	0.5566 (2)	0.30982 (9)	0.0455 (6)
H14A	−0.1331	0.5656	0.3336	0.055*
C15	−0.0056 (8)	−0.1503 (4)	0.59944 (11)	0.0733 (10)
H15A	−0.0236	−0.2179	0.6209	0.110*
H15B	−0.1585	−0.1453	0.5790	0.110*
H15C	0.0102	−0.0776	0.6180	0.110*
C16	0.7123 (5)	0.4166 (2)	0.19693 (9)	0.0417 (5)
H16A	0.6065	0.3437	0.1961	0.050*
H16B	0.8265	0.4133	0.2251	0.050*
C17	0.8749 (7)	0.4267 (3)	0.15168 (9)	0.0539 (7)
H17A	0.9934	0.3593	0.1496	0.081*
H17B	0.9749	0.5003	0.1525	0.081*
H17C	0.7603	0.4270	0.1240	0.081*

	U11	U22	U33	U12	U13	U23
O1	0.0414 (11)	0.0677 (13)	0.0635 (12)	0.0013 (10)	0.0107 (10)	0.0136 (11)
O2	0.0805 (16)	0.0535 (11)	0.0528 (10)	−0.0074 (11)	0.0050 (12)	0.0097 (10)
O3	0.0437 (10)	0.0448 (9)	0.0465 (9)	0.0102 (8)	0.0082 (9)	0.0071 (8)
O4	0.0578 (12)	0.0402 (8)	0.0519 (10)	0.0089 (8)	0.0092 (10)	0.0100 (8)
N1	0.0411 (12)	0.0485 (11)	0.0439 (11)	−0.0042 (9)	0.0058 (10)	0.0092 (9)
N2	0.0441 (13)	0.0508 (11)	0.0445 (11)	−0.0076 (10)	0.0024 (11)	0.0059 (10)
C1	0.0379 (13)	0.0411 (11)	0.0380 (12)	−0.0011 (10)	−0.0006 (10)	−0.0033 (9)
C2	0.0437 (15)	0.0510 (13)	0.0461 (13)	0.0085 (11)	0.0032 (12)	−0.0063 (12)
C3	0.0602 (18)	0.0456 (13)	0.0496 (15)	0.0083 (13)	−0.0036 (14)	0.0001 (12)
C4	0.0525 (16)	0.0438 (12)	0.0416 (12)	−0.0070 (12)	−0.0032 (12)	−0.0025 (11)
C5	0.0522 (17)	0.0563 (14)	0.0462 (14)	0.0015 (13)	0.0104 (13)	0.0041 (12)
C6	0.0467 (14)	0.0447 (12)	0.0500 (14)	0.0076 (11)	0.0051 (13)	−0.0009 (11)
C7	0.0383 (13)	0.0431 (11)	0.0431 (12)	−0.0021 (10)	0.0031 (12)	−0.0028 (10)
C8	0.0413 (14)	0.0457 (12)	0.0448 (13)	−0.0052 (11)	0.0028 (11)	0.0008 (10)
C9	0.0387 (13)	0.0383 (10)	0.0411 (12)	−0.0036 (9)	−0.0027 (11)	0.0007 (10)
C10	0.0353 (13)	0.0359 (10)	0.0448 (12)	0.0015 (9)	−0.0023 (10)	0.0017 (9)
C11	0.0321 (11)	0.0354 (10)	0.0415 (11)	−0.0018 (9)	0.0004 (10)	−0.0005 (9)
C12	0.0350 (12)	0.0314 (9)	0.0457 (12)	0.0003 (9)	−0.0014 (11)	0.0010 (9)
C13	0.0419 (14)	0.0344 (11)	0.0549 (14)	0.0030 (10)	0.0051 (13)	−0.0016 (10)
C14	0.0430 (14)	0.0454 (12)	0.0480 (13)	−0.0020 (11)	0.0075 (12)	−0.0017 (11)
C15	0.069 (2)	0.099 (3)	0.0512 (16)	−0.021 (2)	0.0028 (18)	0.0182 (18)
C16	0.0397 (13)	0.0379 (11)	0.0474 (13)	0.0053 (10)	0.0016 (12)	0.0000 (10)
C17	0.0583 (18)	0.0576 (15)	0.0460 (14)	0.0112 (14)	0.0044 (14)	−0.0024 (12)

O1—C7	1.229 (3)	C6—H6A	0.9300
O2—C4	1.373 (3)	C8—C9	1.455 (3)
O2—C15	1.431 (5)	C8—H8A	0.9300
O3—C11	1.366 (3)	C9—C14	1.390 (4)
O3—C16	1.443 (3)	C9—C10	1.400 (4)
O4—C12	1.358 (3)	C10—C11	1.385 (3)
O4—H1O4	0.8198	C10—H10A	0.9300
N1—C7	1.356 (4)	C11—C12	1.403 (3)
N1—N2	1.386 (3)	C12—C13	1.386 (4)
N1—H1N1	0.8977	C13—C14	1.389 (3)
N2—C8	1.286 (4)	C13—H13A	0.9300
C1—C6	1.396 (4)	C14—H14A	0.9300
C1—C2	1.398 (4)	C15—H15A	0.9600
C1—C7	1.481 (3)	C15—H15B	0.9600
C2—C3	1.368 (4)	C15—H15C	0.9600
C2—H2A	0.9300	C16—C17	1.501 (4)
C3—C4	1.388 (4)	C16—H16A	0.9700
C3—H3A	0.9300	C16—H16B	0.9700
C4—C5	1.384 (4)	C17—H17A	0.9600
C5—C6	1.385 (4)	C17—H17B	0.9600
C5—H5A	0.9300	C17—H17C	0.9600
C4—O2—C15	117.6 (3)	C11—C10—C9	120.1 (2)
C11—O3—C16	116.72 (18)	C11—C10—H10A	119.9
C12—O4—H1O4	109.3	C9—C10—H10A	119.9
C7—N1—N2	117.9 (2)	O3—C11—C10	125.8 (2)
C7—N1—H1N1	120.2	O3—C11—C12	114.3 (2)
N2—N1—H1N1	115.3	C10—C11—C12	119.9 (2)
C8—N2—N1	114.5 (2)	O4—C12—C13	118.3 (2)
C6—C1—C2	117.8 (2)	O4—C12—C11	121.8 (2)
C6—C1—C7	123.4 (2)	C13—C12—C11	119.9 (2)
C2—C1—C7	118.8 (2)	C12—C13—C14	119.9 (2)
C3—C2—C1	120.9 (3)	C12—C13—H13A	120.0
C3—C2—H2A	119.5	C14—C13—H13A	120.0
C1—C2—H2A	119.5	C13—C14—C9	120.6 (2)
C2—C3—C4	120.5 (3)	C13—C14—H14A	119.7
C2—C3—H3A	119.8	C9—C14—H14A	119.7
C4—C3—H3A	119.8	O2—C15—H15A	109.5
O2—C4—C5	124.2 (3)	O2—C15—H15B	109.5
O2—C4—C3	115.8 (3)	H15A—C15—H15B	109.5
C5—C4—C3	120.1 (3)	O2—C15—H15C	109.5
C4—C5—C6	119.1 (3)	H15A—C15—H15C	109.5
C4—C5—H5A	120.5	H15B—C15—H15C	109.5
C6—C5—H5A	120.5	O3—C16—C17	107.8 (2)
C5—C6—C1	121.7 (3)	O3—C16—H16A	110.2
C5—C6—H6A	119.2	C17—C16—H16A	110.2
C1—C6—H6A	119.2	O3—C16—H16B	110.2
O1—C7—N1	122.6 (2)	C17—C16—H16B	110.2
O1—C7—C1	122.4 (3)	H16A—C16—H16B	108.5
N1—C7—C1	115.0 (2)	C16—C17—H17A	109.5
N2—C8—C9	122.2 (2)	C16—C17—H17B	109.5
N2—C8—H8A	118.9	H17A—C17—H17B	109.5
C9—C8—H8A	118.9	C16—C17—H17C	109.5
C14—C9—C10	119.5 (2)	H17A—C17—H17C	109.5
C14—C9—C8	118.6 (2)	H17B—C17—H17C	109.5
C10—C9—C8	122.0 (2)
C7—N1—N2—C8	−172.3 (2)	N1—N2—C8—C9	−178.2 (2)
C6—C1—C2—C3	1.4 (4)	N2—C8—C9—C14	−162.0 (3)
C7—C1—C2—C3	−179.0 (3)	N2—C8—C9—C10	18.0 (4)
C1—C2—C3—C4	−1.6 (4)	C14—C9—C10—C11	0.1 (4)
C15—O2—C4—C5	10.0 (4)	C8—C9—C10—C11	−179.9 (2)
C15—O2—C4—C3	−170.4 (3)	C16—O3—C11—C10	3.6 (3)
C2—C3—C4—O2	−179.4 (3)	C16—O3—C11—C12	−175.6 (2)
C2—C3—C4—C5	0.3 (4)	C9—C10—C11—O3	−177.6 (2)
O2—C4—C5—C6	−179.2 (3)	C9—C10—C11—C12	1.6 (4)
C3—C4—C5—C6	1.2 (4)	O3—C11—C12—O4	−1.8 (3)
C4—C5—C6—C1	−1.3 (4)	C10—C11—C12—O4	178.9 (2)
C2—C1—C6—C5	0.1 (4)	O3—C11—C12—C13	177.1 (2)
C7—C1—C6—C5	−179.5 (3)	C10—C11—C12—C13	−2.2 (4)
N2—N1—C7—O1	0.8 (4)	O4—C12—C13—C14	180.0 (2)
N2—N1—C7—C1	−178.3 (2)	C11—C12—C13—C14	1.0 (4)
C6—C1—C7—O1	150.6 (3)	C12—C13—C14—C9	0.7 (4)
C2—C1—C7—O1	−29.0 (4)	C10—C9—C14—C13	−1.2 (4)
C6—C1—C7—N1	−30.2 (4)	C8—C9—C14—C13	178.8 (2)
C2—C1—C7—N1	150.2 (2)	C11—O3—C16—C17	178.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O3	0.82	2.41	2.683 (2)	100
O4—H1O4···O1i	0.82	2.21	2.981 (2)	156
N1—H1N1···O1ii	0.90	2.10	2.994 (3)	172
C10—H10A···O4iii	0.93	2.55	3.462 (3)	168
C16—H16B···Cg1i	0.97	2.68	3.499 (2)	142

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
O4—H1O4⋯O3	0.82	2.41	2.683 (2)	100
O4—H1O4⋯O1i	0.82	2.21	2.981 (2)	156
N1—H1N1⋯O1ii	0.90	2.10	2.994 (3)	172
C10—H10A⋯O4iii	0.93	2.55	3.462 (3)	168
C16—H16B⋯Cg1i	0.97	2.68	3.499 (2)	142

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