(E)-N'-(3,4-Dimeth-oxy-benzyl-idene)-4-meth-oxy-benzohydrazide.

In the title compound, C(17)H(18)N(2)O(4), the azomethine double bond adopts an E conformation with an N-N-C-C torsion angle of -178.3 (3)°. The benzene rings are almost coplaner, with a dihedral angle of 2.98 (14)° between their mean planes. In the crystal, the molecules are linked by N-H⋯O hydrogen bonds, resulting in chains of mol-ecules lying parallel to the b axis. The structure is further consolidated by rather weak C-H⋯O hydrogen-bonding inter-actions, resulting in six-membered rings about inversion centers linked into chains arranged parallel to the b axis.

Related literature

For the biological activity of benzohydrazides, see: Bayrak et al. (2009 ▶). For the crystal structures of related benzohydrazides, see: Fun et al. (2011 ▶); Lu et al. (2009 ▶.

Experimental

Crystal data

C17H18N2O4

M = 314.33

Monoclinic,

a = 14.191 (2) Å

b = 5.0109 (8) Å

c = 22.535 (4) Å

β = 99.010 (4)°

V = 1582.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 273 K

0.23 × 0.20 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.979, T max = 0.996

8638 measured reflections

2891 independent reflections

1400 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.115

S = 0.96

2891 reflections

216 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.16 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034228/pv2573sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034228/pv2573Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034228/pv2573Isup3.cml

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

C17H18N2O4	F(000) = 664
Mr = 314.33	Dx = 1.319 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 506 reflections
a = 14.191 (2) Å	θ = 2.9–18.7°
b = 5.0109 (8) Å	µ = 0.10 mm−1
c = 22.535 (4) Å	T = 273 K
β = 99.010 (4)°	Plate, colorles
V = 1582.7 (5) Å3	0.23 × 0.20 × 0.04 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2891 independent reflections
Radiation source: fine-focus sealed tube	1400 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.080
ω scan	θmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→16
Tmin = 0.979, Tmax = 0.996	k = −5→5
8638 measured reflections	l = −27→26

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0319P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
2891 reflections	Δρmax = 0.18 e Å−3
216 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (5)

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	0.08439 (16)	0.0973 (5)	0.30744 (8)	0.0533 (7)
O2	0.02249 (17)	−0.2411 (5)	0.37757 (9)	0.0517 (7)
O3	0.27009 (17)	−0.4724 (4)	0.67207 (9)	0.0559 (7)
O4	0.47170 (17)	−0.0216 (5)	0.92189 (8)	0.0597 (7)
N1	0.23561 (18)	−0.0850 (5)	0.58675 (10)	0.0423 (8)
N2	0.2763 (2)	−0.0366 (6)	0.64635 (11)	0.0429 (8)
C1	0.1311 (2)	−0.0799 (6)	0.46462 (12)	0.0383 (8)
H1B	0.1098	−0.2050	0.4900	0.046*
C2	0.0930 (2)	−0.0774 (6)	0.40460 (13)	0.0376 (8)
C3	0.1267 (2)	0.1102 (7)	0.36613 (12)	0.0390 (9)
C4	0.1959 (2)	0.2892 (6)	0.38871 (13)	0.0426 (9)
H4A	0.2185	0.4120	0.3634	0.051*
C5	0.2323 (2)	0.2866 (6)	0.44979 (13)	0.0447 (9)
H5A	0.2784	0.4110	0.4651	0.054*
C6	0.2013 (2)	0.1033 (7)	0.48788 (12)	0.0392 (9)
C7	0.2418 (2)	0.1119 (7)	0.55156 (13)	0.0435 (9)
H7A	0.2732	0.2658	0.5670	0.052*
C8	0.2912 (2)	−0.2397 (7)	0.68566 (13)	0.0380 (8)
C9	0.3389 (2)	−0.1642 (6)	0.74719 (12)	0.0330 (8)
C10	0.4038 (2)	0.0405 (6)	0.75824 (12)	0.0399 (9)
H10A	0.4164	0.1460	0.7265	0.048*
C11	0.4510 (2)	0.0934 (6)	0.81608 (12)	0.0401 (9)
H11A	0.4957	0.2301	0.8226	0.048*
C12	0.4308 (2)	−0.0582 (7)	0.86330 (13)	0.0395 (8)
C13	0.3653 (2)	−0.2629 (7)	0.85314 (13)	0.0468 (9)
H13A	0.3510	−0.3640	0.8852	0.056*
C14	0.3212 (2)	−0.3176 (6)	0.79592 (13)	0.0444 (9)
H14A	0.2787	−0.4597	0.7894	0.053*
C15	0.5404 (3)	0.1858 (7)	0.93508 (14)	0.0697 (12)
H15A	0.5626	0.1906	0.9776	0.105*
H15B	0.5116	0.3540	0.9224	0.105*
H15C	0.5932	0.1527	0.9142	0.105*
C16	−0.0236 (2)	−0.4110 (7)	0.41506 (13)	0.0567 (10)
H16A	−0.0743	−0.5066	0.3909	0.085*
H16B	−0.0494	−0.3050	0.4442	0.085*
H16C	0.0218	−0.5356	0.4353	0.085*
C17	0.1047 (3)	0.3085 (7)	0.26842 (13)	0.0626 (12)
H17A	0.0644	0.2907	0.2302	0.094*
H17B	0.1703	0.2987	0.2630	0.094*
H17C	0.0929	0.4774	0.2860	0.094*
H2A	0.2850 (18)	0.139 (5)	0.6573 (11)	0.030 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0620 (18)	0.0641 (18)	0.0305 (13)	−0.0093 (14)	−0.0034 (11)	0.0056 (12)
O2	0.0634 (18)	0.0525 (16)	0.0359 (13)	−0.0183 (14)	−0.0021 (12)	0.0002 (12)
O3	0.089 (2)	0.0261 (15)	0.0470 (14)	−0.0012 (13)	−0.0073 (12)	−0.0045 (12)
O4	0.0687 (19)	0.0761 (19)	0.0306 (13)	−0.0173 (15)	−0.0034 (11)	0.0017 (12)
N1	0.057 (2)	0.0356 (19)	0.0302 (15)	0.0044 (15)	−0.0065 (13)	−0.0070 (13)
N2	0.071 (2)	0.0230 (18)	0.0297 (15)	−0.0009 (16)	−0.0083 (13)	−0.0061 (14)
C1	0.049 (2)	0.031 (2)	0.0339 (18)	−0.0020 (18)	0.0027 (15)	0.0015 (15)
C2	0.044 (2)	0.034 (2)	0.0320 (18)	−0.0010 (18)	−0.0022 (15)	−0.0040 (16)
C3	0.042 (2)	0.045 (2)	0.0280 (18)	0.0055 (19)	0.0007 (15)	−0.0007 (17)
C4	0.045 (2)	0.045 (2)	0.0366 (19)	−0.0044 (18)	0.0030 (16)	0.0067 (16)
C5	0.049 (2)	0.040 (2)	0.042 (2)	−0.0053 (18)	−0.0050 (17)	−0.0007 (17)
C6	0.046 (2)	0.037 (2)	0.0331 (18)	0.0037 (18)	−0.0003 (16)	0.0000 (16)
C7	0.054 (3)	0.035 (2)	0.038 (2)	−0.0009 (19)	−0.0042 (17)	−0.0055 (17)
C8	0.050 (2)	0.027 (2)	0.0359 (19)	0.0054 (18)	0.0037 (16)	0.0010 (17)
C9	0.041 (2)	0.024 (2)	0.0337 (18)	0.0031 (16)	0.0054 (15)	−0.0005 (15)
C10	0.050 (2)	0.040 (2)	0.0301 (18)	−0.0014 (19)	0.0058 (15)	0.0014 (16)
C11	0.044 (2)	0.040 (2)	0.0349 (19)	−0.0064 (18)	0.0021 (15)	0.0005 (16)
C12	0.039 (2)	0.049 (2)	0.0289 (18)	0.0020 (19)	0.0016 (15)	−0.0004 (17)
C13	0.055 (3)	0.052 (2)	0.0323 (19)	−0.005 (2)	0.0052 (17)	0.0064 (17)
C14	0.055 (3)	0.033 (2)	0.045 (2)	−0.0077 (17)	0.0053 (17)	−0.0008 (17)
C15	0.077 (3)	0.081 (3)	0.043 (2)	−0.015 (3)	−0.015 (2)	−0.004 (2)
C16	0.051 (3)	0.065 (3)	0.054 (2)	−0.013 (2)	0.0067 (18)	−0.005 (2)
C17	0.073 (3)	0.069 (3)	0.045 (2)	0.008 (2)	0.003 (2)	0.018 (2)

O1—C3	1.366 (3)	C7—H7A	0.9300
O1—C17	1.434 (3)	C8—C9	1.493 (4)
O2—C2	1.362 (3)	C9—C10	1.374 (4)
O2—C16	1.428 (3)	C9—C14	1.395 (4)
O3—C8	1.231 (3)	C10—C11	1.394 (4)
O4—C12	1.369 (3)	C10—H10A	0.9300
O4—C15	1.424 (4)	C11—C12	1.373 (4)
N1—C7	1.277 (4)	C11—H11A	0.9300
N1—N2	1.398 (3)	C12—C13	1.379 (4)
N2—C8	1.344 (4)	C13—C14	1.370 (4)
N2—H2A	0.92 (3)	C13—H13A	0.9300
C1—C2	1.376 (4)	C14—H14A	0.9300
C1—C6	1.395 (4)	C15—H15A	0.9600
C1—H1B	0.9300	C15—H15B	0.9600
C2—C3	1.412 (4)	C15—H15C	0.9600
C3—C4	1.367 (4)	C16—H16A	0.9600
C4—C5	1.393 (4)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C5—C6	1.375 (4)	C17—H17A	0.9600
C5—H5A	0.9300	C17—H17B	0.9600
C6—C7	1.460 (4)	C17—H17C	0.9600
C3—O1—C17	117.3 (3)	C9—C10—C11	121.4 (3)
C2—O2—C16	117.9 (2)	C9—C10—H10A	119.3
C12—O4—C15	118.2 (3)	C11—C10—H10A	119.3
C7—N1—N2	113.9 (3)	C12—C11—C10	119.4 (3)
C8—N2—N1	120.0 (3)	C12—C11—H11A	120.3
C8—N2—H2A	123.2 (16)	C10—C11—H11A	120.3
N1—N2—H2A	116.4 (16)	O4—C12—C11	124.4 (3)
C2—C1—C6	120.7 (3)	O4—C12—C13	115.6 (3)
C2—C1—H1B	119.6	C11—C12—C13	120.0 (3)
C6—C1—H1B	119.6	C14—C13—C12	120.1 (3)
O2—C2—C1	125.6 (3)	C14—C13—H13A	119.9
O2—C2—C3	115.0 (3)	C12—C13—H13A	119.9
C1—C2—C3	119.4 (3)	C13—C14—C9	121.2 (3)
O1—C3—C4	124.9 (3)	C13—C14—H14A	119.4
O1—C3—C2	115.0 (3)	C9—C14—H14A	119.4
C4—C3—C2	120.1 (3)	O4—C15—H15A	109.5
C3—C4—C5	119.7 (3)	O4—C15—H15B	109.5
C3—C4—H4A	120.2	H15A—C15—H15B	109.5
C5—C4—H4A	120.2	O4—C15—H15C	109.5
C6—C5—C4	121.2 (3)	H15A—C15—H15C	109.5
C6—C5—H5A	119.4	H15B—C15—H15C	109.5
C4—C5—H5A	119.4	O2—C16—H16A	109.5
C5—C6—C1	118.9 (3)	O2—C16—H16B	109.5
C5—C6—C7	118.6 (3)	H16A—C16—H16B	109.5
C1—C6—C7	122.4 (3)	O2—C16—H16C	109.5
N1—C7—C6	122.2 (3)	H16A—C16—H16C	109.5
N1—C7—H7A	118.9	H16B—C16—H16C	109.5
C6—C7—H7A	118.9	O1—C17—H17A	109.5
O3—C8—N2	123.1 (3)	O1—C17—H17B	109.5
O3—C8—C9	121.9 (3)	H17A—C17—H17B	109.5
N2—C8—C9	114.9 (3)	O1—C17—H17C	109.5
C10—C9—C14	117.8 (3)	H17A—C17—H17C	109.5
C10—C9—C8	123.4 (3)	H17B—C17—H17C	109.5
C14—C9—C8	118.7 (3)
C7—N1—N2—C8	−167.3 (3)	C1—C6—C7—N1	19.1 (5)
C16—O2—C2—C1	7.2 (5)	N1—N2—C8—O3	−0.4 (5)
C16—O2—C2—C3	−171.8 (3)	N1—N2—C8—C9	177.5 (3)
C6—C1—C2—O2	−178.0 (3)	O3—C8—C9—C10	146.6 (3)
C6—C1—C2—C3	1.1 (5)	N2—C8—C9—C10	−31.3 (5)
C17—O1—C3—C4	−8.7 (5)	O3—C8—C9—C14	−29.8 (5)
C17—O1—C3—C2	170.4 (3)	N2—C8—C9—C14	152.3 (3)
O2—C2—C3—O1	−0.7 (4)	C14—C9—C10—C11	0.4 (5)
C1—C2—C3—O1	−179.9 (3)	C8—C9—C10—C11	−176.0 (3)
O2—C2—C3—C4	178.4 (3)	C9—C10—C11—C12	−1.5 (5)
C1—C2—C3—C4	−0.7 (5)	C15—O4—C12—C11	−0.6 (5)
O1—C3—C4—C5	178.6 (3)	C15—O4—C12—C13	179.6 (3)
C2—C3—C4—C5	−0.4 (5)	C10—C11—C12—O4	−179.0 (3)
C3—C4—C5—C6	1.3 (5)	C10—C11—C12—C13	0.8 (5)
C4—C5—C6—C1	−1.0 (5)	O4—C12—C13—C14	−179.3 (3)
C4—C5—C6—C7	−179.6 (3)	C11—C12—C13—C14	0.9 (5)
C2—C1—C6—C5	−0.2 (5)	C12—C13—C14—C9	−2.0 (5)
C2—C1—C6—C7	178.4 (3)	C10—C9—C14—C13	1.4 (5)
N2—N1—C7—C6	−178.3 (3)	C8—C9—C14—C13	177.9 (3)
C5—C6—C7—N1	−162.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.92 (3)	1.99 (3)	2.890 (4)	166 (2)
C15—H15A···O4ii	0.96	2.54	3.357 (4)	143
C17—H17A···O2iii	0.96	2.55	3.505 (4)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.92 (3)	1.99 (3)	2.890 (4)	166 (2)
C15—H15A⋯O4ii	0.96	2.54	3.357 (4)	143
C17—H17A⋯O2iii	0.96	2.55	3.505 (4)	172

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