N'-(3,4-Dimethoxy-benzyl-idene)acetohydrazide.

In the title mol-ecule, C(11)H(14)N(2)O(3), the acetohydrazide group is planar 0.084 (1) Å and forms a dihedral angle of 19.7 (1)° with the benzene ring. One of the meth-oxy groups is coplanar with the attached benzene ring within 0.052 (3) Å, whereas the other is slightly twisted [C-O-C-C = 6.3 (3)°]. The mol-ecule adopts a trans configuration with respect to the C=N bond. In the crystal, the mol-ecules are linked into chains along the a axis by N-H⋯O hydrogen bonds and the chains are cross-linked into a three-dimensional network by C-H⋯O hydrogen bonds.

Related literature

For general background to Schiff bases, see: Cimerman et al. (1997 ▶); Offe et al. (1952 ▶); Richardson et al. (1988 ▶). For related structures, see: Li & Jian (2008 ▶); Tamboura et al. (2009 ▶).

Experimental

Crystal data

C11H14N2O3

M = 222.24

Orthorhombic,

a = 8.794 (3) Å

b = 10.920 (3) Å

c = 24.418 (7) Å

V = 2345.0 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 223 K

0.24 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.977, T max = 0.979

11332 measured reflections

2070 independent reflections

1819 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.133

S = 1.10

2070 reflections

149 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027366/ci2855sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027366/ci2855Isup2.hkl

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

C11H14N2O3	F(000) = 944
Mr = 222.24	Dx = 1.259 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2070 reflections
a = 8.794 (3) Å	θ = 1.7–25.0°
b = 10.920 (3) Å	µ = 0.09 mm−1
c = 24.418 (7) Å	T = 223 K
V = 2345.0 (12) Å3	Block, colourless
Z = 8	0.24 × 0.21 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	2070 independent reflections
Radiation source: fine-focus sealed tube	1819 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.977, Tmax = 0.979	k = −12→12
11332 measured reflections	l = −27→28

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.6946P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2070 reflections	Δρmax = 0.15 e Å−3
149 parameters	Δρmin = −0.12 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: 0.0113 (16)

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	−0.00337 (17)	0.67057 (13)	0.22113 (6)	0.0725 (5)
O2	−0.21387 (16)	0.81158 (15)	0.18477 (6)	0.0738 (5)
O3	−0.07522 (17)	1.32783 (14)	0.01901 (7)	0.0735 (5)
C3	−0.0722 (2)	0.83356 (17)	0.16379 (7)	0.0516 (5)
C7	0.1114 (2)	0.93669 (17)	0.10716 (7)	0.0519 (5)
C4	0.0432 (2)	0.75598 (17)	0.18390 (8)	0.0537 (5)
C6	0.2227 (2)	0.8587 (2)	0.12649 (8)	0.0621 (5)
H6	0.3216	0.8663	0.1135	0.074*
C8	−0.0381 (2)	0.92289 (17)	0.12603 (7)	0.0507 (5)
H8	−0.1143	0.9742	0.1130	0.061*
C10	0.0460 (2)	1.29542 (18)	−0.00180 (8)	0.0556 (5)
C5	0.1896 (2)	0.76932 (19)	0.16500 (9)	0.0625 (6)
H5	0.2663	0.7184	0.1780	0.075*
C9	0.1527 (2)	1.03131 (19)	0.06757 (8)	0.0564 (5)
H9	0.2501	1.0303	0.0528	0.068*
C11	0.1217 (3)	1.3670 (2)	−0.04662 (9)	0.0702 (6)
H11A	0.0706	1.3517	−0.0807	0.105*
H11B	0.2261	1.3423	−0.0496	0.105*
H11C	0.1169	1.4528	−0.0382	0.105*
C2	−0.3390 (2)	0.8771 (3)	0.16274 (10)	0.0825 (7)
H2A	−0.3234	0.9633	0.1680	0.124*
H2B	−0.4307	0.8524	0.1810	0.124*
H2C	−0.3476	0.8600	0.1243	0.124*
C1	0.1076 (3)	0.5863 (2)	0.24102 (11)	0.0827 (8)
H1A	0.1518	0.5429	0.2108	0.124*
H1B	0.0601	0.5291	0.2655	0.124*
H1C	0.1857	0.6303	0.2602	0.124*
N2	0.12042 (19)	1.19408 (15)	0.01359 (6)	0.0569 (4)
H2	0.2071	1.1778	−0.0010	0.068*
N1	0.06138 (18)	1.11504 (14)	0.05240 (6)	0.0544 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0779 (10)	0.0661 (9)	0.0736 (10)	−0.0030 (7)	−0.0097 (8)	0.0243 (8)
O2	0.0572 (9)	0.0863 (11)	0.0779 (10)	0.0039 (8)	0.0052 (7)	0.0262 (8)
O3	0.0634 (9)	0.0642 (10)	0.0929 (11)	0.0057 (7)	−0.0005 (8)	0.0069 (8)
C3	0.0533 (11)	0.0536 (11)	0.0479 (10)	−0.0003 (9)	−0.0020 (8)	−0.0001 (8)
C7	0.0581 (11)	0.0515 (11)	0.0462 (10)	0.0034 (9)	−0.0006 (8)	−0.0017 (8)
C4	0.0650 (12)	0.0477 (10)	0.0486 (10)	−0.0021 (9)	−0.0085 (9)	0.0030 (8)
C6	0.0545 (11)	0.0661 (13)	0.0656 (12)	0.0041 (10)	0.0016 (10)	0.0063 (10)
C8	0.0560 (11)	0.0488 (10)	0.0473 (10)	0.0068 (8)	−0.0032 (8)	0.0010 (8)
C10	0.0587 (12)	0.0505 (11)	0.0576 (11)	−0.0049 (9)	−0.0092 (9)	−0.0037 (9)
C5	0.0624 (12)	0.0574 (12)	0.0679 (13)	0.0097 (10)	−0.0096 (10)	0.0071 (10)
C9	0.0559 (11)	0.0605 (12)	0.0529 (10)	0.0042 (10)	0.0022 (9)	0.0027 (9)
C11	0.0918 (16)	0.0530 (12)	0.0659 (13)	−0.0018 (11)	−0.0030 (12)	0.0071 (10)
C2	0.0548 (12)	0.1042 (19)	0.0886 (17)	0.0095 (13)	0.0055 (12)	0.0167 (15)
C1	0.0994 (18)	0.0651 (14)	0.0836 (16)	0.0000 (13)	−0.0244 (14)	0.0224 (13)
N2	0.0577 (9)	0.0551 (10)	0.0578 (9)	0.0008 (8)	0.0040 (8)	0.0078 (8)
N1	0.0572 (9)	0.0525 (9)	0.0536 (9)	−0.0042 (8)	0.0005 (7)	0.0052 (7)

O1—C4	1.365 (2)	C10—C11	1.501 (3)
O1—C1	1.427 (3)	C5—H5	0.93
O2—C3	1.368 (2)	C9—N1	1.272 (2)
O2—C2	1.419 (3)	C9—H9	0.93
O3—C10	1.233 (2)	C11—H11A	0.96
C3—C8	1.375 (3)	C11—H11B	0.96
C3—C4	1.410 (3)	C11—H11C	0.96
C7—C6	1.381 (3)	C2—H2A	0.96
C7—C8	1.401 (3)	C2—H2B	0.96
C7—C9	1.461 (3)	C2—H2C	0.96
C4—C5	1.375 (3)	C1—H1A	0.96
C6—C5	1.386 (3)	C1—H1B	0.96
C6—H6	0.93	C1—H1C	0.96
C8—H8	0.93	N2—N1	1.383 (2)
C10—N2	1.340 (2)	N2—H2	0.86
C4—O1—C1	117.52 (18)	N1—C9—H9	118.5
C3—O2—C2	118.41 (16)	C7—C9—H9	118.5
O2—C3—C8	125.05 (17)	C10—C11—H11A	109.5
O2—C3—C4	114.81 (17)	C10—C11—H11B	109.5
C8—C3—C4	120.14 (18)	H11A—C11—H11B	109.5
C6—C7—C8	119.11 (18)	C10—C11—H11C	109.5
C6—C7—C9	119.09 (18)	H11A—C11—H11C	109.5
C8—C7—C9	121.80 (17)	H11B—C11—H11C	109.5
O1—C4—C5	125.20 (18)	O2—C2—H2A	109.5
O1—C4—C3	115.24 (18)	O2—C2—H2B	109.5
C5—C4—C3	119.55 (18)	H2A—C2—H2B	109.5
C7—C6—C5	121.14 (19)	O2—C2—H2C	109.5
C7—C6—H6	119.4	H2A—C2—H2C	109.5
C5—C6—H6	119.4	H2B—C2—H2C	109.5
C3—C8—C7	120.12 (17)	O1—C1—H1A	109.5
C3—C8—H8	119.9	O1—C1—H1B	109.5
C7—C8—H8	119.9	H1A—C1—H1B	109.5
O3—C10—N2	122.96 (19)	O1—C1—H1C	109.5
O3—C10—C11	122.33 (19)	H1A—C1—H1C	109.5
N2—C10—C11	114.71 (19)	H1B—C1—H1C	109.5
C4—C5—C6	119.93 (19)	C10—N2—N1	121.62 (17)
C4—C5—H5	120.0	C10—N2—H2	119.2
C6—C5—H5	120.0	N1—N2—H2	119.2
N1—C9—C7	122.97 (18)	C9—N1—N2	114.28 (17)
C2—O2—C3—C8	6.3 (3)	C6—C7—C8—C3	0.7 (3)
C2—O2—C3—C4	−173.8 (2)	C9—C7—C8—C3	−179.28 (17)
C1—O1—C4—C5	−1.7 (3)	O1—C4—C5—C6	179.13 (18)
C1—O1—C4—C3	177.38 (18)	C3—C4—C5—C6	0.1 (3)
O2—C3—C4—O1	0.1 (2)	C7—C6—C5—C4	1.1 (3)
C8—C3—C4—O1	−179.94 (16)	C6—C7—C9—N1	−171.95 (19)
O2—C3—C4—C5	179.25 (18)	C8—C7—C9—N1	8.1 (3)
C8—C3—C4—C5	−0.8 (3)	O3—C10—N2—N1	3.4 (3)
C8—C7—C6—C5	−1.5 (3)	C11—C10—N2—N1	−176.62 (17)
C9—C7—C6—C5	178.54 (18)	C7—C9—N1—N2	−178.40 (17)
O2—C3—C8—C7	−179.67 (18)	C10—N2—N1—C9	−171.88 (17)
C4—C3—C8—C7	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.86	1.97	2.803 (2)	164
C1—H1C···O2ii	0.96	2.55	3.435 (3)	153
C11—H11C···O3iii	0.96	2.47	3.425 (3)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.86	1.97	2.803 (2)	164
C1—H1C⋯O2ii	0.96	2.55	3.435 (3)	153
C11—H11C⋯O3iii	0.96	2.47	3.425 (3)	174

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