(E)-4-Hy-droxy-N'-(3,4,5-trimeth-oxy-benzyl-idene)benzohydrazide.

The title benzohydrazide derivative, C(17)H(18)N(2)O(5), exists in a trans conformation with respect to the C=N double bond. The dihedral angle between the benzene rings is 19.41 (5)°. The two meth-oxy groups at the meta positions of the trimeth-oxy-benzene group are almost coplanar with the ring [C-O-C-C = 1.62 (16) and 178.33 (10)°], whereas the third meth-oxy group, at the para position, is (+)-synclinal with the ring. In the crystal, mol-ecules are linked by N-H⋯O and bifurcated O-H⋯(N,O) hydrogen bonds, as well as weak C-H⋯O inter-actions, into sheets lying parallel to the ac plane. A C-H⋯π inter-action also occurs.

Related literature

For a related structure and background references to benzohydrazide derivatives, see: Fun et al. (2011 ▶). For related structures, see: Li & Ban (2009 ▶); Zhang (2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H18N2O5

M = 330.33

Orthorhombic,

a = 14.4623 (8) Å

b = 10.9202 (6) Å

c = 19.5592 (10) Å

V = 3089.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 297 K

0.39 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.979

20210 measured reflections

4500 independent reflections

3777 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.03

4500 reflections

228 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.32 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/S1600536811041535/hb6444sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041535/hb6444Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041535/hb6444Isup3.cml

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

C17H18N2O5	Dx = 1.421 Mg m−3
Mr = 330.33	Melting point = 533–532 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4500 reflections
a = 14.4623 (8) Å	θ = 2.1–30.0°
b = 10.9202 (6) Å	µ = 0.11 mm−1
c = 19.5592 (10) Å	T = 297 K
V = 3089.0 (3) Å3	Block, colorless
Z = 8	0.39 × 0.21 × 0.20 mm
F(000) = 1392

Bruker SMART APEXII CCD diffractometer	4500 independent reflections
Radiation source: fine-focus sealed tube	3777 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 8.33 pixels mm-1	θmax = 30.0°, θmin = 2.1°
ω scans	h = −18→20
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→14
Tmin = 0.960, Tmax = 0.979	l = −27→27
20210 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0512P)2 + 1.5827P] where P = (Fo2 + 2Fc2)/3
4500 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.32 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	0.02505 (5)	1.10904 (8)	0.80535 (4)	0.01825 (17)
O2	−0.32653 (6)	1.14816 (8)	0.61694 (4)	0.01926 (18)
H1O2	−0.3790 (16)	1.119 (2)	0.6311 (11)	0.051 (6)*
O3	0.32914 (5)	0.88335 (8)	1.01826 (4)	0.01920 (18)
O4	0.29967 (5)	0.71610 (8)	1.11552 (4)	0.01747 (17)
O5	0.13085 (6)	0.63448 (8)	1.14433 (4)	0.01937 (18)
N1	−0.06135 (6)	0.96981 (9)	0.86248 (5)	0.01526 (18)
H1N1	−0.1150 (12)	0.9362 (16)	0.8709 (9)	0.029 (4)*
N2	0.01401 (6)	0.94312 (9)	0.90309 (5)	0.01538 (18)
C1	−0.12442 (7)	1.07047 (10)	0.76129 (5)	0.0147 (2)
C2	−0.11500 (7)	1.16838 (11)	0.71558 (6)	0.0165 (2)
H2A	−0.0627	1.2178	0.7178	0.020*
C3	−0.18213 (8)	1.19281 (11)	0.66718 (6)	0.0167 (2)
H3A	−0.1747	1.2578	0.6369	0.020*
C4	−0.26122 (7)	1.11954 (10)	0.66390 (5)	0.0155 (2)
C5	−0.26994 (7)	1.01888 (11)	0.70742 (6)	0.0163 (2)
H5A	−0.3212	0.9678	0.7039	0.020*
C6	−0.20211 (7)	0.99504 (10)	0.75593 (6)	0.0162 (2)
H6A	−0.2085	0.9283	0.7851	0.019*
C7	−0.04843 (7)	1.05222 (10)	0.81117 (5)	0.0142 (2)
C8	−0.00007 (7)	0.87131 (10)	0.95390 (6)	0.0155 (2)
H8A	−0.0592	0.8419	0.9630	0.019*
C9	0.07833 (7)	0.83586 (10)	0.99769 (5)	0.0144 (2)
C10	0.16646 (7)	0.88419 (10)	0.98592 (5)	0.0154 (2)
H10A	0.1756	0.9421	0.9517	0.019*
C11	0.24005 (7)	0.84492 (10)	1.02576 (5)	0.0153 (2)
C12	0.22580 (7)	0.75942 (10)	1.07816 (5)	0.0152 (2)
C13	0.13721 (7)	0.71439 (10)	1.09113 (5)	0.0153 (2)
C14	0.06307 (7)	0.75202 (10)	1.05023 (5)	0.0155 (2)
H14A	0.0040	0.7213	1.0580	0.019*
C15	0.34575 (8)	0.97270 (12)	0.96645 (6)	0.0208 (2)
H15A	0.4092	0.9982	0.9682	0.031*
H15B	0.3064	1.0422	0.9739	0.031*
H15C	0.3328	0.9379	0.9224	0.031*
C16	0.33986 (12)	0.80230 (13)	1.16153 (8)	0.0366 (4)
H16A	0.4044	0.7842	1.1672	0.055*
H16B	0.3093	0.7973	1.2050	0.055*
H16C	0.3330	0.8834	1.1433	0.055*
C17	0.04118 (8)	0.58866 (12)	1.16066 (6)	0.0221 (2)
H17A	0.0450	0.5378	1.2006	0.033*
H17B	0.0181	0.5414	1.1230	0.033*
H17C	0.0001	0.6560	1.1694	0.033*

	U11	U22	U33	U12	U13	U23
O1	0.0125 (3)	0.0233 (4)	0.0190 (4)	−0.0017 (3)	0.0000 (3)	0.0030 (3)
O2	0.0142 (4)	0.0264 (4)	0.0172 (4)	−0.0013 (3)	−0.0031 (3)	0.0046 (3)
O3	0.0124 (4)	0.0266 (4)	0.0186 (4)	−0.0017 (3)	−0.0006 (3)	0.0051 (3)
O4	0.0140 (3)	0.0186 (4)	0.0197 (4)	0.0021 (3)	−0.0051 (3)	0.0012 (3)
O5	0.0163 (4)	0.0222 (4)	0.0197 (4)	−0.0015 (3)	−0.0027 (3)	0.0078 (3)
N1	0.0108 (4)	0.0191 (4)	0.0158 (4)	−0.0002 (3)	−0.0020 (3)	0.0032 (3)
N2	0.0124 (4)	0.0185 (4)	0.0152 (4)	0.0024 (3)	−0.0027 (3)	−0.0001 (3)
C1	0.0121 (4)	0.0184 (5)	0.0135 (4)	0.0012 (4)	0.0003 (3)	0.0009 (4)
C2	0.0139 (5)	0.0193 (5)	0.0164 (5)	−0.0026 (4)	0.0002 (4)	0.0015 (4)
C3	0.0164 (5)	0.0187 (5)	0.0150 (5)	−0.0016 (4)	0.0001 (4)	0.0033 (4)
C4	0.0134 (4)	0.0197 (5)	0.0134 (4)	0.0016 (4)	0.0004 (4)	0.0000 (4)
C5	0.0132 (4)	0.0180 (5)	0.0176 (5)	−0.0014 (4)	−0.0002 (4)	0.0012 (4)
C6	0.0147 (5)	0.0170 (5)	0.0167 (5)	0.0003 (4)	0.0003 (4)	0.0031 (4)
C7	0.0124 (4)	0.0167 (5)	0.0134 (4)	0.0021 (4)	0.0011 (3)	−0.0001 (4)
C8	0.0132 (4)	0.0177 (5)	0.0157 (5)	0.0007 (4)	−0.0011 (4)	−0.0008 (4)
C9	0.0135 (4)	0.0157 (5)	0.0138 (4)	0.0017 (4)	−0.0009 (3)	−0.0015 (4)
C10	0.0142 (5)	0.0182 (5)	0.0139 (4)	0.0002 (4)	0.0003 (4)	0.0008 (4)
C11	0.0124 (4)	0.0184 (5)	0.0152 (4)	0.0002 (4)	0.0008 (4)	−0.0010 (4)
C12	0.0132 (4)	0.0173 (5)	0.0151 (4)	0.0028 (4)	−0.0016 (3)	0.0001 (4)
C13	0.0160 (5)	0.0163 (5)	0.0136 (4)	0.0010 (4)	−0.0010 (4)	0.0005 (4)
C14	0.0132 (4)	0.0172 (5)	0.0160 (5)	0.0000 (4)	−0.0006 (4)	0.0002 (4)
C15	0.0168 (5)	0.0258 (6)	0.0199 (5)	−0.0023 (4)	0.0012 (4)	0.0046 (4)
C16	0.0504 (9)	0.0268 (7)	0.0326 (7)	0.0135 (6)	−0.0256 (7)	−0.0118 (6)
C17	0.0182 (5)	0.0249 (6)	0.0233 (6)	−0.0036 (4)	−0.0010 (4)	0.0079 (5)

O1—C7	1.2358 (13)	C5—H5A	0.9300
O2—C4	1.3542 (13)	C6—H6A	0.9300
O2—H1O2	0.87 (2)	C8—C9	1.4727 (14)
O3—C11	1.3630 (13)	C8—H8A	0.9300
O3—C15	1.4270 (14)	C9—C14	1.3939 (15)
O4—C12	1.3780 (12)	C9—C10	1.3986 (15)
O4—C16	1.4262 (15)	C10—C11	1.3871 (15)
O5—C13	1.3611 (13)	C10—H10A	0.9300
O5—C17	1.4262 (14)	C11—C12	1.4016 (15)
N1—C7	1.3608 (14)	C12—C13	1.3957 (15)
N1—N2	1.3797 (12)	C13—C14	1.3995 (15)
N1—H1N1	0.874 (18)	C14—H14A	0.9300
N2—C8	1.2821 (15)	C15—H15A	0.9600
C1—C6	1.3971 (15)	C15—H15B	0.9600
C1—C2	1.4004 (15)	C15—H15C	0.9600
C1—C7	1.4831 (14)	C16—H16A	0.9600
C2—C3	1.3820 (15)	C16—H16B	0.9600
C2—H2A	0.9300	C16—H16C	0.9600
C3—C4	1.3974 (15)	C17—H17A	0.9600
C3—H3A	0.9300	C17—H17B	0.9600
C4—C5	1.3959 (15)	C17—H17C	0.9600
C5—C6	1.3894 (15)
C4—O2—H1O2	108.0 (14)	C10—C9—C8	120.44 (10)
C11—O3—C15	116.49 (9)	C11—C10—C9	119.34 (10)
C12—O4—C16	115.09 (9)	C11—C10—H10A	120.3
C13—O5—C17	117.23 (9)	C9—C10—H10A	120.3
C7—N1—N2	117.12 (9)	O3—C11—C10	124.72 (10)
C7—N1—H1N1	122.6 (11)	O3—C11—C12	115.01 (9)
N2—N1—H1N1	120.2 (11)	C10—C11—C12	120.26 (10)
C8—N2—N1	116.75 (9)	O4—C12—C13	119.62 (10)
C6—C1—C2	118.72 (10)	O4—C12—C11	120.16 (9)
C6—C1—C7	124.48 (10)	C13—C12—C11	120.17 (10)
C2—C1—C7	116.77 (10)	O5—C13—C12	115.27 (9)
C3—C2—C1	121.09 (10)	O5—C13—C14	125.00 (10)
C3—C2—H2A	119.5	C12—C13—C14	119.73 (10)
C1—C2—H2A	119.5	C9—C14—C13	119.54 (10)
C2—C3—C4	119.73 (10)	C9—C14—H14A	120.2
C2—C3—H3A	120.1	C13—C14—H14A	120.2
C4—C3—H3A	120.1	O3—C15—H15A	109.5
O2—C4—C5	122.16 (10)	O3—C15—H15B	109.5
O2—C4—C3	118.03 (10)	H15A—C15—H15B	109.5
C5—C4—C3	119.79 (10)	O3—C15—H15C	109.5
C6—C5—C4	120.01 (10)	H15A—C15—H15C	109.5
C6—C5—H5A	120.0	H15B—C15—H15C	109.5
C4—C5—H5A	120.0	O4—C16—H16A	109.5
C5—C6—C1	120.57 (10)	O4—C16—H16B	109.5
C5—C6—H6A	119.7	H16A—C16—H16B	109.5
C1—C6—H6A	119.7	O4—C16—H16C	109.5
O1—C7—N1	121.20 (10)	H16A—C16—H16C	109.5
O1—C7—C1	120.61 (10)	H16B—C16—H16C	109.5
N1—C7—C1	118.18 (9)	O5—C17—H17A	109.5
N2—C8—C9	119.29 (10)	O5—C17—H17B	109.5
N2—C8—H8A	120.4	H17A—C17—H17B	109.5
C9—C8—H8A	120.4	O5—C17—H17C	109.5
C14—C9—C10	120.90 (10)	H17A—C17—H17C	109.5
C14—C9—C8	118.65 (10)	H17B—C17—H17C	109.5
C7—N1—N2—C8	175.78 (10)	C8—C9—C10—C11	−176.91 (10)
C6—C1—C2—C3	1.83 (17)	C15—O3—C11—C10	1.62 (16)
C7—C1—C2—C3	179.98 (10)	C15—O3—C11—C12	−178.52 (10)
C1—C2—C3—C4	0.52 (17)	C9—C10—C11—O3	178.62 (10)
C2—C3—C4—O2	178.38 (10)	C9—C10—C11—C12	−1.23 (16)
C2—C3—C4—C5	−2.91 (17)	C16—O4—C12—C13	−111.02 (14)
O2—C4—C5—C6	−178.41 (10)	C16—O4—C12—C11	71.28 (15)
C3—C4—C5—C6	2.94 (16)	O3—C11—C12—O4	−2.99 (15)
C4—C5—C6—C1	−0.57 (17)	C10—C11—C12—O4	176.88 (10)
C2—C1—C6—C5	−1.80 (16)	O3—C11—C12—C13	179.33 (10)
C7—C1—C6—C5	−179.80 (10)	C10—C11—C12—C13	−0.80 (17)
N2—N1—C7—O1	−6.63 (15)	C17—O5—C13—C12	178.33 (10)
N2—N1—C7—C1	172.15 (9)	C17—O5—C13—C14	−1.93 (16)
C6—C1—C7—O1	167.40 (11)	O4—C12—C13—O5	4.06 (15)
C2—C1—C7—O1	−10.63 (15)	C11—C12—C13—O5	−178.24 (10)
C6—C1—C7—N1	−11.39 (16)	O4—C12—C13—C14	−175.69 (10)
C2—C1—C7—N1	170.58 (10)	C11—C12—C13—C14	2.00 (16)
N1—N2—C8—C9	177.83 (9)	C10—C9—C14—C13	−0.90 (16)
N2—C8—C9—C14	−176.20 (10)	C8—C9—C14—C13	178.12 (10)
N2—C8—C9—C10	2.83 (16)	O5—C13—C14—C9	179.12 (10)
C14—C9—C10—C11	2.10 (16)	C12—C13—C14—C9	−1.15 (16)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1i	0.87 (2)	1.87 (2)	2.6646 (11)	152 (2)
O2—H1O2···N2i	0.87 (2)	2.56 (2)	3.2381 (13)	136.2 (18)
N1—H1N1···O4ii	0.874 (17)	2.088 (17)	2.8891 (12)	152.0 (16)
C6—H6A···O4ii	0.93	2.51	3.4116 (14)	165
C16—H16B···Cg1iii	0.96	2.63	3.4572 (17)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1i	0.87 (2)	1.87 (2)	2.6646 (11)	152 (2)
O2—H1O2⋯N2i	0.87 (2)	2.56 (2)	3.2381 (13)	136.2 (18)
N1—H1N1⋯O4ii	0.874 (17)	2.088 (17)	2.8891 (12)	152.0 (16)
C6—H6A⋯O4ii	0.93	2.51	3.4116 (14)	165
C16—H16B⋯Cg1iii	0.96	2.63	3.4572 (17)	145

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