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

The asymmetric unit of the title compound, C(11)H(14)N(2)O(3), contains two independent mol-ecules with close conformations; the C=N-N-C torsion angle is 176.4 (1)° in both mol-ecules. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into chains running along the [01] direction.

Related literature

For general background to the applications of 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

Triclinic,

a = 8.339 (3) Å

b = 8.349 (3) Å

c = 8.663 (3) Å

α = 94.717 (12)°

β = 95.210 (8)°

γ = 94.298 (12)°

V = 596.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 223 K

0.24 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.987, T max = 0.990

3236 measured reflections

2054 independent reflections

1890 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.110

S = 1.12

2054 reflections

290 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.15 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/S1600536809028608/cv2586sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028608/cv2586Isup2.hkl

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

C11H14N2O3	Z = 2
Mr = 222.24	F(000) = 236
Triclinic, P1	Dx = 1.237 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.339 (3) Å	Cell parameters from 2054 reflections
b = 8.349 (3) Å	θ = 2.4–25.0°
c = 8.663 (3) Å	µ = 0.09 mm−1
α = 94.717 (12)°	T = 223 K
β = 95.210 (8)°	Block, colourless
γ = 94.298 (12)°	0.24 × 0.21 × 0.19 mm
V = 596.6 (3) Å3

Bruker SMART CCD area-detector diffractometer	2054 independent reflections
Radiation source: fine-focus sealed tube	1890 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
Tmin = 0.987, Tmax = 0.990	k = −9→9
3236 measured reflections	l = −10→9

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0737P)2 + 0.0315P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2054 reflections	Δρmax = 0.18 e Å−3
290 parameters	Δρmin = −0.15 e Å−3
3 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: 0.101 (14)

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
O4	0.0007 (2)	−0.4436 (3)	0.6700 (2)	0.0538 (6)
O5	0.2416 (3)	−0.2594 (3)	0.8028 (3)	0.0604 (6)
O2	0.6714 (3)	0.0884 (3)	1.2796 (3)	0.0691 (7)
O3	−0.0291 (3)	0.4482 (3)	1.2193 (3)	0.0668 (7)
N2	0.0775 (3)	0.4780 (3)	0.9931 (3)	0.0520 (6)
H2	0.0686	0.5156	0.9036	0.062*
O1	0.8549 (3)	0.0361 (3)	1.0637 (3)	0.0659 (7)
N3	0.2418 (3)	0.2632 (3)	0.5009 (3)	0.0473 (6)
N1	0.2086 (3)	0.3943 (3)	1.0364 (3)	0.0476 (6)
C15	0.1580 (3)	−0.1968 (3)	0.6814 (3)	0.0428 (6)
O6	0.4783 (3)	0.5122 (3)	0.5771 (3)	0.0796 (8)
C18	0.1933 (3)	−0.0476 (4)	0.6295 (3)	0.0449 (6)
H17	0.2816	0.0189	0.6767	0.054*
C6	0.4492 (3)	0.2834 (3)	0.9661 (3)	0.0460 (7)
N4	0.2566 (3)	0.4016 (3)	0.4235 (3)	0.0508 (6)
H4	0.1872	0.4136	0.3465	0.061*
C17	0.0956 (3)	0.0041 (4)	0.5047 (3)	0.0456 (7)
C2	0.7255 (3)	0.1177 (4)	1.0226 (3)	0.0479 (7)
C9	0.3061 (4)	0.3708 (4)	0.9334 (3)	0.0474 (7)
H9	0.2861	0.4097	0.8365	0.057*
C5	0.4882 (3)	0.2291 (4)	1.1140 (3)	0.0476 (7)
H6	0.4221	0.2488	1.1932	0.057*
C20	0.1279 (4)	0.1605 (4)	0.4428 (3)	0.0497 (7)
H20	0.0619	0.1854	0.3571	0.060*
C10	−0.0362 (4)	0.5003 (3)	1.0920 (3)	0.0484 (7)
C14	−0.0720 (4)	−0.2478 (4)	0.4888 (4)	0.0535 (7)
H14	−0.1612	−0.3137	0.4425	0.064*
C13	0.0239 (3)	−0.2980 (3)	0.6102 (3)	0.0446 (7)
C7	0.5492 (4)	0.2542 (4)	0.8501 (3)	0.0508 (7)
H7	0.5252	0.2903	0.7526	0.061*
C16	−0.0345 (4)	−0.0966 (4)	0.4350 (4)	0.0556 (8)
H18	−0.0980	−0.0638	0.3515	0.067*
C11	−0.1735 (4)	0.5935 (5)	1.0337 (4)	0.0623 (8)
H11A	−0.1585	0.6212	0.9303	0.093*
H11B	−0.1758	0.6903	1.1012	0.093*
H11C	−0.2737	0.5286	1.0324	0.093*
C4	0.6230 (4)	0.1474 (4)	1.1414 (3)	0.0495 (7)
C3	0.6859 (4)	0.1710 (4)	0.8788 (4)	0.0548 (8)
H3	0.7517	0.1510	0.7994	0.066*
C21	0.3770 (4)	0.5174 (4)	0.4662 (3)	0.0524 (7)
C12	−0.1272 (4)	−0.5549 (5)	0.5953 (4)	0.0641 (9)
H12A	−0.1310	−0.6517	0.6478	0.096*
H12B	−0.1082	−0.5803	0.4887	0.096*
H12C	−0.2282	−0.5072	0.5992	0.096*
C22	0.3783 (5)	0.6553 (4)	0.3640 (5)	0.0694 (9)
H22A	0.2882	0.6378	0.2856	0.104*
H22B	0.4771	0.6615	0.3151	0.104*
H22C	0.3704	0.7545	0.4263	0.104*
C8	0.5745 (5)	0.1116 (5)	1.4029 (4)	0.0672 (9)
H5A	0.6225	0.0673	1.4932	0.101*
H5B	0.4687	0.0584	1.3734	0.101*
H5C	0.5660	0.2248	1.4263	0.101*
C1	0.9669 (5)	0.0112 (5)	0.9511 (5)	0.0775 (11)
H1A	1.0525	−0.0478	0.9934	0.116*
H1B	1.0112	0.1136	0.9244	0.116*
H1C	0.9125	−0.0489	0.8596	0.116*
C19	0.3937 (5)	−0.1813 (5)	0.8631 (5)	0.0800 (12)
H16A	0.4381	−0.2371	0.9475	0.120*
H16B	0.3805	−0.0720	0.9001	0.120*
H16C	0.4656	−0.1820	0.7826	0.120*

	U11	U22	U33	U12	U13	U23
O4	0.0553 (11)	0.0539 (13)	0.0528 (12)	−0.0019 (9)	−0.0015 (9)	0.0211 (10)
O5	0.0625 (12)	0.0572 (13)	0.0598 (12)	−0.0038 (10)	−0.0176 (10)	0.0294 (10)
O2	0.0710 (15)	0.1024 (19)	0.0436 (11)	0.0453 (14)	0.0073 (10)	0.0281 (12)
O3	0.0708 (15)	0.0814 (16)	0.0526 (13)	0.0172 (12)	0.0043 (11)	0.0239 (12)
N2	0.0547 (13)	0.0591 (15)	0.0458 (14)	0.0141 (11)	−0.0031 (12)	0.0261 (12)
O1	0.0580 (13)	0.0810 (16)	0.0649 (15)	0.0280 (12)	0.0127 (11)	0.0158 (12)
N3	0.0566 (14)	0.0477 (14)	0.0414 (13)	0.0132 (11)	0.0059 (11)	0.0173 (11)
N1	0.0507 (13)	0.0483 (14)	0.0447 (13)	0.0096 (10)	−0.0062 (11)	0.0161 (10)
C15	0.0420 (14)	0.0495 (16)	0.0393 (14)	0.0100 (12)	0.0007 (11)	0.0161 (12)
O6	0.0796 (17)	0.0751 (17)	0.0801 (18)	0.0006 (13)	−0.0203 (14)	0.0187 (14)
C18	0.0451 (14)	0.0492 (16)	0.0418 (14)	0.0081 (12)	0.0012 (11)	0.0125 (12)
C6	0.0512 (15)	0.0472 (16)	0.0384 (14)	0.0000 (12)	−0.0047 (12)	0.0102 (12)
N4	0.0613 (14)	0.0500 (14)	0.0431 (13)	0.0082 (11)	−0.0015 (11)	0.0199 (11)
C17	0.0505 (16)	0.0472 (16)	0.0422 (15)	0.0143 (12)	0.0045 (12)	0.0128 (12)
C2	0.0483 (16)	0.0502 (17)	0.0464 (16)	0.0092 (13)	0.0046 (13)	0.0073 (13)
C9	0.0559 (16)	0.0490 (16)	0.0377 (14)	0.0054 (12)	−0.0041 (12)	0.0151 (12)
C5	0.0508 (16)	0.0535 (17)	0.0398 (14)	0.0120 (13)	0.0009 (12)	0.0089 (12)
C20	0.0583 (17)	0.0485 (17)	0.0444 (15)	0.0142 (13)	−0.0010 (13)	0.0150 (13)
C10	0.0560 (17)	0.0440 (16)	0.0443 (16)	0.0034 (12)	−0.0055 (14)	0.0100 (12)
C14	0.0471 (15)	0.0567 (18)	0.0551 (18)	0.0026 (13)	−0.0091 (13)	0.0126 (14)
C13	0.0463 (15)	0.0473 (16)	0.0425 (15)	0.0068 (12)	0.0039 (12)	0.0154 (12)
C7	0.0595 (18)	0.0554 (17)	0.0379 (14)	0.0002 (14)	0.0021 (13)	0.0138 (13)
C16	0.0579 (17)	0.0571 (19)	0.0532 (18)	0.0137 (14)	−0.0092 (14)	0.0207 (15)
C11	0.063 (2)	0.063 (2)	0.0614 (19)	0.0159 (16)	0.0004 (16)	0.0106 (16)
C4	0.0532 (16)	0.0593 (18)	0.0381 (15)	0.0133 (14)	−0.0005 (12)	0.0137 (13)
C3	0.0588 (17)	0.0587 (18)	0.0487 (17)	0.0019 (14)	0.0106 (14)	0.0117 (14)
C21	0.0583 (18)	0.0516 (18)	0.0488 (17)	0.0116 (14)	0.0021 (14)	0.0097 (13)
C12	0.066 (2)	0.065 (2)	0.060 (2)	−0.0107 (16)	0.0014 (16)	0.0203 (16)
C22	0.085 (2)	0.0533 (19)	0.071 (2)	0.0030 (17)	0.0061 (19)	0.0154 (17)
C8	0.081 (2)	0.087 (2)	0.0413 (17)	0.0353 (19)	0.0107 (16)	0.0201 (16)
C1	0.063 (2)	0.078 (3)	0.099 (3)	0.0206 (18)	0.031 (2)	0.010 (2)
C19	0.073 (2)	0.073 (2)	0.088 (3)	−0.0081 (18)	−0.037 (2)	0.033 (2)

O4—C13	1.367 (3)	C5—H6	0.9300
O4—C12	1.431 (4)	C20—H20	0.9300
O5—C15	1.370 (3)	C10—C11	1.505 (4)
O5—C19	1.417 (4)	C14—C13	1.376 (4)
O2—C4	1.370 (3)	C14—C16	1.405 (4)
O2—C8	1.407 (4)	C14—H14	0.9300
O3—C10	1.216 (4)	C7—C3	1.393 (5)
N2—C10	1.348 (4)	C7—H7	0.9300
N2—N1	1.380 (3)	C16—H18	0.9300
N2—H2	0.8600	C11—H11A	0.9600
O1—C2	1.355 (4)	C11—H11B	0.9600
O1—C1	1.424 (5)	C11—H11C	0.9600
N3—C20	1.270 (4)	C3—H3	0.9300
N3—N4	1.385 (3)	C21—O6	1.225 (4)
N1—C9	1.274 (4)	C21—C22	1.510 (5)
C15—C18	1.379 (4)	C12—H12A	0.9600
C15—C13	1.412 (4)	C12—H12B	0.9600
O6—C21	1.225 (4)	C12—H12C	0.9600
C18—C17	1.410 (4)	C22—H22A	0.9600
C18—H17	0.9300	C22—H22B	0.9600
C6—C7	1.381 (4)	C22—H22C	0.9600
C6—C5	1.413 (4)	C8—H5A	0.9600
C6—C9	1.463 (4)	C8—H5B	0.9600
N4—C21	1.345 (4)	C8—H5C	0.9600
N4—H4	0.8600	C1—H1A	0.9600
C17—C16	1.381 (4)	C1—H1B	0.9600
C17—C20	1.468 (4)	C1—H1C	0.9600
C2—C3	1.377 (4)	C19—H16A	0.9600
C2—C4	1.415 (4)	C19—H16B	0.9600
C9—H9	0.9300	C19—H16C	0.9600
C5—C4	1.370 (4)
C13—O4—C12	117.5 (2)	C17—C16—H18	119.6
C15—O5—C19	118.3 (2)	C14—C16—H18	119.6
C4—O2—C8	117.6 (2)	C10—C11—H11A	109.5
C10—N2—N1	119.6 (2)	C10—C11—H11B	109.5
C10—N2—H2	120.2	H11A—C11—H11B	109.5
N1—N2—H2	120.2	C10—C11—H11C	109.5
C2—O1—C1	117.2 (3)	H11A—C11—H11C	109.5
C20—N3—N4	114.6 (2)	H11B—C11—H11C	109.5
C9—N1—N2	115.8 (2)	C5—C4—O2	125.2 (3)
O5—C15—C18	125.6 (3)	C5—C4—C2	120.5 (2)
O5—C15—C13	114.2 (2)	O2—C4—C2	114.3 (2)
C18—C15—C13	120.2 (2)	C2—C3—C7	121.2 (3)
C15—C18—C17	120.0 (3)	C2—C3—H3	119.4
C15—C18—H17	120.0	C7—C3—H3	119.4
C17—C18—H17	120.0	O6—C21—N4	123.7 (3)
C7—C6—C5	119.2 (3)	O6—C21—N4	123.7 (3)
C7—C6—C9	119.3 (2)	O6—C21—C22	122.4 (3)
C5—C6—C9	121.5 (3)	O6—C21—C22	122.4 (3)
C21—N4—N3	121.4 (2)	N4—C21—C22	114.0 (3)
C21—N4—H4	119.3	O4—C12—H12A	109.5
N3—N4—H4	119.3	O4—C12—H12B	109.5
C16—C17—C18	119.3 (2)	H12A—C12—H12B	109.5
C16—C17—C20	118.0 (2)	O4—C12—H12C	109.5
C18—C17—C20	122.7 (3)	H12A—C12—H12C	109.5
O1—C2—C3	126.3 (3)	H12B—C12—H12C	109.5
O1—C2—C4	115.0 (2)	C21—C22—H22A	109.5
C3—C2—C4	118.6 (3)	C21—C22—H22B	109.5
N1—C9—C6	120.6 (2)	H22A—C22—H22B	109.5
N1—C9—H9	119.7	C21—C22—H22C	109.5
C6—C9—H9	119.7	H22A—C22—H22C	109.5
C4—C5—C6	120.3 (3)	H22B—C22—H22C	109.5
C4—C5—H6	119.8	O2—C8—H5A	109.5
C6—C5—H6	119.8	O2—C8—H5B	109.5
N3—C20—C17	122.9 (3)	H5A—C8—H5B	109.5
N3—C20—H20	118.5	O2—C8—H5C	109.5
C17—C20—H20	118.5	H5A—C8—H5C	109.5
O3—C10—N2	122.5 (3)	H5B—C8—H5C	109.5
O3—C10—C11	122.2 (3)	O1—C1—H1A	109.5
N2—C10—C11	115.3 (3)	O1—C1—H1B	109.5
C13—C14—C16	119.6 (3)	H1A—C1—H1B	109.5
C13—C14—H14	120.2	O1—C1—H1C	109.5
C16—C14—H14	120.2	H1A—C1—H1C	109.5
O4—C13—C14	124.7 (2)	H1B—C1—H1C	109.5
O4—C13—C15	115.3 (2)	O5—C19—H16A	109.5
C14—C13—C15	120.0 (2)	O5—C19—H16B	109.5
C6—C7—C3	120.2 (3)	H16A—C19—H16B	109.5
C6—C7—H7	119.9	O5—C19—H16C	109.5
C3—C7—H7	119.9	H16A—C19—H16C	109.5
C17—C16—C14	120.9 (2)	H16B—C19—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4i	0.86	2.11	2.950 (3)	165
N2—H2···O5i	0.86	2.54	3.154 (3)	129
C7—H7···O6	0.93	2.52	3.372 (3)	152
C12—H12B···O3ii	0.96	2.51	3.434 (4)	162
C12—H12C···O6iii	0.96	2.45	3.367 (4)	159
C16—H18···O2iv	0.93	2.45	3.244 (3)	144
N4—H4···O3v	0.86	2.08	2.907 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4i	0.86	2.11	2.950 (3)	165
N2—H2⋯O5i	0.86	2.54	3.154 (3)	129
C7—H7⋯O6	0.93	2.52	3.372 (3)	152
C12—H12B⋯O3ii	0.96	2.51	3.434 (4)	162
C12—H12C⋯O6iii	0.96	2.45	3.367 (4)	159
C16—H18⋯O2iv	0.93	2.45	3.244 (3)	144
N4—H4⋯O3v	0.86	2.08	2.907 (3)	161

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