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

Abstract

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.

Full text

Page 1

N0 0 0-(3,4-Dimethoxybenzylidene)aceto-
hydrazide
Bao-Cheng Zhou,a,b* Lu-Ping Lv,cWen-Bo Yu,cWei-Wei
Licand Xian-Chao Hud
aDepartment of Applied Chemistry, Zhejiang Sci-tech University, Hangzhou 310018,
People’s Republic of China,bKey Laboratory of Advanced Textile Materials and
Manufacturing Technology, Ministry of Education, Zhejiang Sci-Tech University,
Hangzhou 310018, People’s Republic of China,cDepartment of Chemical
Engineering, Hangzhou Vocational and Technical College, Hangzhou 310018,
People’s Republic of China, anddResearch Center of Analysis and Measurement,
Zhejiang University of Technology, Hangzhou 310014, People’s Republic of China
Correspondence e-mail: zjlgzbc@126.com
Received 7 July 2009; accepted 20 July 2009
Key indicators: single-crystal X-ray study; T = 223 K; mean ?(C–C) = 0.004 A ˚;
R factor = 0.036; wR factor = 0.110; data-to-parameter ratio = 7.1.
The asymmetric unit of the title compound, C11H14N2O3,
containstwo independent molecules with close conformations;
the C
N—N—C torsion angle is 176.4 (1)?in both molecules.
In the crystal, intermolecular N—H???O and C—H???O
hydrogen bonds link the molecules into chains running along
the [011] 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
Mr= 222.24
Triclinic, P1
a = 8.339 (3) A˚
b = 8.349 (3) A˚
c = 8.663 (3) A˚
? = 94.717 (12)?
? = 95.210 (8)?
? = 94.298 (12)?
V = 596.6 (3) A˚3
Z = 2
Mo K? radiation
? = 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)
Tmin= 0.987, Tmax= 0.990
3236 measured reflections
2054 independent reflections
1890 reflections with I > 2?(I)
Rint= 0.017
Refinement
R[F2> 2?(F2)] = 0.036
wR(F2) = 0.110
S = 1.12
2054 reflections
290 parameters
3 restraints
H-atom parameters constrained
??max= 0.18 e A˚?3
??min= ?0.15 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
N2—H2???O4i
N2—H2???O5i
C7—H7???O6
C12—H12B???O3ii
C12—H12C???O6iii
C16—H18???O2iv
N4—H4???O3v
Symmetry codes: (i) x;y þ 1;z; (ii) x;y ? 1;z ? 1; (iii) x ? 1;y ? 1;z; (iv) x ? 1;y;z ? 1;
(v) x;y;z ? 1.
D—HH???AD???AD—H???A
0.86
0.86
0.93
0.96
0.96
0.93
0.86
2.11
2.54
2.52
2.51
2.45
2.45
2.08
2.950 (3)
3.154 (3)
3.372 (3)
3.434 (4)
3.367 (4)
3.244 (3)
2.907 (3)
165
129
152
162
159
144
161
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,
SHELXTL (Sheldrick, 2008); software used to prepare material for
publication: SHELXTL.
2008); molecular graphics:
The authors thank Zhejiang Sci-tech University and the
Science and Technology Project of Zhejiang Province for
financial support (grant No. 2007 F70077) .
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: CV2586).
References
Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,
Wisconsin, USA.
Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal Chim. Acta, 343, 145–153.
Li, Y.-F. & Jian, F.-F. (2008). Acta Cryst. E64, o2409.
Offe, H. A., Siefen, W. & Domagk, G. (1952). Z. Naturforsch. Teil B, 7, 446–
447.
Richardson, D., Baker, E., Ponka, P., Wilairat, P., Vitolo, M. L. & Webb, J.
(1988). Thalassemia: Pathophysiology and Management, Part B, p. 81. New
York: Alan R. Liss.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Tamboura, F. B., Gaye, M., Sall, A. S., Barry, A. H. & Bah, Y. (2009). Acta
Cryst. E65, m160–m161.
organic compounds
o1964
Zhou et al.
doi:10.1107/S1600536809028608
Acta Cryst. (2009). E65, o1964
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

Page 2

supplementary materials

Page 3

supplementary materials
sup-1
Acta Cryst. (2009). E65, o1964 [ doi:10.1107/S1600536809028608 ]
N'-(3,4-Dimethoxybenzylidene)acetohydrazide
B.-C. Zhou, L.-P. Lv, W.-B. Yu, W.-W. Li and X.-C. Hu
Comment
Schiff bases have attracted much attention due to their possible analytical applications (Cimerman et al., 1997). They are
also important ligands, which have been reported to have mild bacteriostatic activity and potential oral iron-chelating drugs
for genetic disorders such as thalassemia (Offe et al., 1952; Richardson et al., 1988). Metal complexes based on Schiff
bases have received considerable attention because they can be utilized as model compounds of active centres in various
complexes (Tamboura et al., 2009). We report here the crystal structure of the title compound.
The title compound (Fig. 1) crystallizes with two independent molecules in the asymmetric unit. The side chains in the two
independent molecules have the same orientations, with the C═N—N—C torsion angle being 176.4 (1)° in both molecules.
The N1/N2//O3/C9/C10/C11 and N3/N4/O6/C20/C21/C22 planes form dihedral angles of 6.00 (5)° and 4.38 (9)°, respect-
ively, with the C2—C7 and C13—C18 planes. The dihedral angle between the two independent benzene rings is 79.39 (7)°.
The bond lengths and angles are comparable to those observed for N'-[1-(4-methoxyphenyl)ethylidene]acetohydrazide (Li
et al., 2008).
In the crystal structure, the molecules are linked into chains running along the [01-1] by N—H···O and C—H···O hydrogen
bonds(Table 1).
Experimental
3,4-Methoxybenzaldehyde (1.66 g, 0.01 mol) and acetohydrazide (0.74 g, 0.01 mol) were dissolved in stirred methanol (25
ml) and left for 2.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the
title compound in 85% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol
solution at room temperature (m.p. 468–470 K).
Refinement
H atoms were positioned geometrically (N-H = 0.86 Å and C-H = 0.93 or 0.96 Å) and refined using a riding model, with
Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(Cmethyl). In the absence of significant anomalous scatterers, 1140 Friedel pairs were
averaged.

Page 4

supplementary materials
sup-2
Figures
Fig. 1. The content of asymmetric unit of the title compound. Displacement ellipsoids are
drawn at the 30% probability level.
N'-(3,4-Dimethoxybenzylidene)acetohydrazide
Crystal data
C11H14N2O3
Mr = 222.24
Z = 2
F000 = 236
Dx = 1.237 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 2054 reflections
θ = 2.4–25.0º
µ = 0.09 mm−1
T = 223 K
Block, colourless
0.24 × 0.21 × 0.19 mm
Triclinic, P1
Hall symbol: P 1
a = 8.339 (3) Å
b = 8.349 (3) Å
c = 8.663 (3) Å
α = 94.717 (12)º
β = 95.210 (8)º
γ = 94.298 (12)º
V = 596.6 (3) Å3
Data collection
Bruker SMART CCD area-detector
diffractometer
Radiation source: fine-focus sealed tube
Monochromator: graphite
T = 223 K
φ and ω scans
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
Tmin = 0.987, Tmax = 0.990
3236 measured reflections
2054 independent reflections
1890 reflections with I > 2σ(I)
Rint = 0.017
θmax = 25.0º
θmin = 2.4º
h = −9→9
k = −9→9
l = −10→9
Refinement
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
wR(F2) = 0.110
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0737P)2 + 0.0315P]

Page 5

supplementary materials
sup-3
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.18 e Å−3
Δρmin = −0.15 e Å−3
Extinction correction: SHELXL97 (Sheldrick, 2008),
Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
S = 1.12
2054 reflections
290 parameters
3 restraints
Primary atom site location: structure-invariant direct
methods
Extinction coefficient: 0.101 (14)
Special details
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, convention-
al 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 calculat-
ing 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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
0.0007 (2)
0.2416 (3)
0.6714 (3)
−0.0291 (3)
0.0775 (3)
0.0686
0.8549 (3)
0.2418 (3)
0.2086 (3)
0.1580 (3)
0.4783 (3)
0.1933 (3)
0.2816
0.4492 (3)
0.2566 (3)
0.1872
0.0956 (3)
0.7255 (3)
0.3061 (4)
0.2861
0.4882 (3)
0.4221
0.1279 (4)
0.0619
y
−0.4436 (3)
−0.2594 (3)
0.0884 (3)
0.4482 (3)
0.4780 (3)
0.5156
0.0361 (3)
0.2632 (3)
0.3943 (3)
−0.1968 (3)
0.5122 (3)
−0.0476 (4)
0.0189
0.2834 (3)
0.4016 (3)
0.4136
0.0041 (4)
0.1177 (4)
0.3708 (4)
0.4097
0.2291 (4)
0.2488
0.1605 (4)
0.1854
z
0.6700 (2)
0.8028 (3)
1.2796 (3)
1.2193 (3)
0.9931 (3)
0.9036
1.0637 (3)
0.5009 (3)
1.0364 (3)
0.6814 (3)
0.5771 (3)
0.6295 (3)
0.6767
0.9661 (3)
0.4235 (3)
0.3465
0.5047 (3)
1.0226 (3)
0.9334 (3)
0.8365
1.1140 (3)
1.1932
0.4428 (3)
0.3571
Uiso*/Ueq
0.0538 (6)
0.0604 (6)
0.0691 (7)
0.0668 (7)
0.0520 (6)
0.062*
0.0659 (7)
0.0473 (6)
0.0476 (6)
0.0428 (6)
0.0796 (8)
0.0449 (6)
0.054*
0.0460 (7)
0.0508 (6)
0.061*
0.0456 (7)
0.0479 (7)
0.0474 (7)
0.057*
0.0476 (7)
0.057*
0.0497 (7)
0.060*
O4
O5
O2
O3
N2
H2
O1
N3
N1
C15
O6
C18
H17
C6
N4
H4
C17
C2
C9
H9
C5
H6
C20
H20