organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N′-(3-Meth­oxy­benzyl­­idene)aceto­hydrazide

aDepartment of Chemical Engineering, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China, and bResearch Center of Analysis and Measurement, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
*Correspondence e-mail: zgdhxc@126.com

(Received 20 July 2009; accepted 21 July 2009; online 25 July 2009)

In the title mol­ecule, C10H12N2O2, the acetohydrazide group is planar within 0.012 (1) Å and forms a dihedral angle of 5.25 (8)° with the benzene ring. The meth­oxy group is coplanar with the attached benzene ring [C—O—C—C = 0.1 (2)°]. The mol­ecule adopts a trans configuration with respect to the C=N double bond. In the crystal, mol­ecules are linked into centrosymmetric dimers by N—H⋯O hydrogen bonds and these dimers are linked into a ribbon-like structure along [110] by C—H⋯O hydrogen bonds. In addition, an inter­molecular C—H⋯π inter­action is observed.

Related literature

For general background to the analytical applications of Schiff bases, see: Cimerman et al. (1997[Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145-153.]). For their mild bacteriostatic activity and potential use as oral iron-chelating drugs for genetic disorders such as thalassemia, see: Offe et al. (1952[Offe, H. A., Siefen, W. & Domagk, G. (1952). Z. Naturforsch. Teil B, 7, 446-447.]); Richardson et al. (1988[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.]). For related structures, see: Li & Jian (2008[Li, Y.-F. & Jian, F.-F. (2008). Acta Cryst. E64, o2409.]); Tamboura et al. (2009[Tamboura, F. B., Gaye, M., Sall, A. S., Barry, A. H. & Bah, Y. (2009). Acta Cryst. E65, m160-m161.]).

[Scheme 1]

Experimental

Crystal data
  • C10H12N2O2

  • Mr = 192.22

  • Monoclinic, P 21 /c

  • a = 12.394 (4) Å

  • b = 5.7278 (19) Å

  • c = 15.017 (5) Å

  • β = 107.126 (4)°

  • V = 1018.8 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 223 K

  • 0.23 × 0.22 × 0.18 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.982, Tmax = 0.985

  • 4871 measured reflections

  • 1768 independent reflections

  • 1502 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.116

  • S = 1.07

  • 1768 reflections

  • 130 parameters

  • H-atom parameters constrained

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O2i 0.86 2.04 2.8846 (19) 169
C1—H1B⋯O2ii 0.96 2.49 3.350 (2) 148
C3—H3⋯Cg1iii 0.93 2.83 3.544 (2) 134
Symmetry codes: (i) -x+1, -y-1, -z+1; (ii) x+1, y+1, z; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]. Cg1 is the centroid of the C2-C7 ring.

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Schiff bases have attracted much attention due to the possibility of their analytical applications (Cimerman et al., 1997). They are also important ligands, which have been reported to have mild bacteriostatic activity and are used as 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 (Fig. 1).

The acetohydrazide group is planar and it forms a dihedral angle of 5.25 (8)° with the benzene ring. The methoxy group is coplanar with the attached benzene ring [C1—O1—C2—C3 = 0.1 (2)°]. The molecule adopts a trans configuration with respect to the CN bond. Bond lengths and angles are comparable to those observed for N'-[1-(4-methoxyphenyl)ethylidene]acetohydrazide (Li & Jian, 2008).

The molecules are linked by N—H···O hydrogen bonds into a centrosymmetric dimer. These dimers are linked into a ribbon-like structure along the [110] by C—H···O hydrogen bonds (Table 1 and Fig.2). In addition, an intermolecular C—H···π interaction is observed

Related literature top

For general background to the analytical applications of Schiff bases, see: Cimerman et al. (1997). For their mild bacteriostatic activity and potential use as oral iron-chelating drugs for genetic disorders such as thalassemia, see: Offe et al. (1952); Richardson et al. (1988). For related structures, see: Li & Jian (2008); Tamboura et al. (2009). Cg1 is the centroid of the C2-C7 ring.

Experimental top

3-Methoxybenzaldehyde (1.36 g, 0.01 mol) and acetohydrazide (0.74 g, 0.01 mol) were dissolved in stirred methanol (20 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 83% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 485–487 K).

Refinement top

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). A rotating group model was used for the methyl groups.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level.
[Figure 2] Fig. 2. Part of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.
N'-(3-Methoxybenzylidene)acetohydrazide top
Crystal data top
C10H12N2O2F(000) = 408
Mr = 192.22Dx = 1.253 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1768 reflections
a = 12.394 (4) Åθ = 1.7–25.0°
b = 5.7278 (19) ŵ = 0.09 mm1
c = 15.017 (5) ÅT = 223 K
β = 107.126 (4)°Block, colourless
V = 1018.8 (6) Å30.23 × 0.22 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1768 independent reflections
Radiation source: fine-focus sealed tube1502 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ϕ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1314
Tmin = 0.982, Tmax = 0.985k = 66
4871 measured reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0591P)2 + 0.1504P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
1768 reflectionsΔρmax = 0.14 e Å3
130 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.013 (3)
Crystal data top
C10H12N2O2V = 1018.8 (6) Å3
Mr = 192.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.394 (4) ŵ = 0.09 mm1
b = 5.7278 (19) ÅT = 223 K
c = 15.017 (5) Å0.23 × 0.22 × 0.18 mm
β = 107.126 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1768 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
1502 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.985Rint = 0.025
4871 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.07Δρmax = 0.14 e Å3
1768 reflectionsΔρmin = 0.15 e Å3
130 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.15806 (15)0.4646 (4)0.61337 (12)0.0650 (5)
H1A1.12610.61490.59280.097*
H1B1.21830.43310.58690.097*
H1C1.18700.46370.68010.097*
C20.97784 (11)0.3121 (3)0.61264 (9)0.0406 (4)
C30.96000 (13)0.4924 (3)0.66739 (10)0.0450 (4)
H31.01370.60940.68760.054*
C40.86019 (12)0.4960 (3)0.69187 (11)0.0479 (4)
H40.84750.61750.72860.057*
C50.77987 (12)0.3247 (3)0.66313 (10)0.0449 (4)
H50.71360.33080.68010.054*
C60.79857 (11)0.1412 (2)0.60826 (9)0.0376 (4)
C70.89771 (11)0.1359 (3)0.58332 (9)0.0403 (4)
H70.91080.01420.54680.048*
C80.71693 (11)0.0482 (3)0.57784 (10)0.0407 (4)
H80.72910.16190.53760.049*
C90.46526 (12)0.2813 (3)0.59895 (10)0.0466 (4)
C100.43657 (15)0.1051 (3)0.66193 (13)0.0635 (5)
H10A0.36280.13750.66740.095*
H10B0.43750.04840.63650.095*
H10C0.49110.11320.72240.095*
N10.62907 (10)0.0599 (2)0.60576 (8)0.0427 (3)
N20.55938 (10)0.2483 (2)0.57366 (8)0.0465 (4)
H20.57650.34660.53670.056*
O11.07271 (9)0.2889 (2)0.58390 (7)0.0574 (4)
O20.40548 (9)0.4534 (2)0.57006 (8)0.0591 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0562 (10)0.0801 (13)0.0614 (10)0.0309 (9)0.0216 (8)0.0073 (9)
C20.0391 (8)0.0426 (9)0.0388 (8)0.0071 (6)0.0093 (6)0.0021 (6)
C30.0440 (8)0.0366 (8)0.0478 (8)0.0091 (7)0.0031 (6)0.0001 (6)
C40.0470 (9)0.0380 (9)0.0542 (9)0.0020 (7)0.0081 (7)0.0084 (7)
C50.0377 (8)0.0437 (9)0.0514 (9)0.0026 (7)0.0100 (6)0.0012 (7)
C60.0360 (7)0.0351 (8)0.0378 (7)0.0017 (6)0.0048 (5)0.0032 (6)
C70.0435 (8)0.0387 (8)0.0379 (7)0.0055 (6)0.0108 (6)0.0030 (6)
C80.0386 (8)0.0383 (8)0.0422 (8)0.0028 (6)0.0075 (6)0.0007 (6)
C90.0398 (8)0.0500 (9)0.0491 (9)0.0076 (7)0.0117 (6)0.0014 (7)
C100.0608 (10)0.0665 (12)0.0693 (11)0.0092 (9)0.0285 (8)0.0101 (9)
N10.0372 (7)0.0398 (7)0.0481 (7)0.0070 (5)0.0076 (5)0.0003 (5)
N20.0399 (7)0.0439 (8)0.0555 (8)0.0116 (6)0.0139 (5)0.0073 (6)
O10.0510 (7)0.0670 (8)0.0596 (7)0.0240 (6)0.0249 (5)0.0157 (6)
O20.0502 (7)0.0620 (8)0.0693 (7)0.0217 (6)0.0241 (5)0.0108 (6)
Geometric parameters (Å, º) top
C1—O11.4326 (19)C6—C71.3863 (19)
C1—H1A0.96C6—C81.4623 (19)
C1—H1B0.96C7—H70.93
C1—H1C0.96C8—N11.2786 (19)
C2—O11.3730 (17)C8—H80.93
C2—C31.378 (2)C9—O21.2328 (18)
C2—C71.3929 (19)C9—N21.3423 (19)
C3—C41.391 (2)C9—C101.496 (2)
C3—H30.93C10—H10A0.96
C4—C51.374 (2)C10—H10B0.96
C4—H40.93C10—H10C0.96
C5—C61.396 (2)N1—N21.3774 (17)
C5—H50.93N2—H20.86
O1—C1—H1A109.5C6—C7—C2120.32 (13)
O1—C1—H1B109.5C6—C7—H7119.8
H1A—C1—H1B109.5C2—C7—H7119.8
O1—C1—H1C109.5N1—C8—C6120.94 (13)
H1A—C1—H1C109.5N1—C8—H8119.5
H1B—C1—H1C109.5C6—C8—H8119.5
O1—C2—C3124.24 (13)O2—C9—N2119.69 (14)
O1—C2—C7115.31 (13)O2—C9—C10122.14 (14)
C3—C2—C7120.45 (13)N2—C9—C10118.17 (14)
C2—C3—C4118.71 (13)C9—C10—H10A109.5
C2—C3—H3120.6C9—C10—H10B109.5
C4—C3—H3120.6H10A—C10—H10B109.5
C5—C4—C3121.68 (14)C9—C10—H10C109.5
C5—C4—H4119.2H10A—C10—H10C109.5
C3—C4—H4119.2H10B—C10—H10C109.5
C4—C5—C6119.47 (14)C8—N1—N2115.66 (12)
C4—C5—H5120.3C9—N2—N1121.26 (13)
C6—C5—H5120.3C9—N2—H2119.4
C7—C6—C5119.36 (13)N1—N2—H2119.4
C7—C6—C8119.09 (13)C2—O1—C1117.24 (13)
C5—C6—C8121.54 (13)
O1—C2—C3—C4179.97 (13)C3—C2—C7—C60.6 (2)
C7—C2—C3—C40.6 (2)C7—C6—C8—N1174.14 (12)
C2—C3—C4—C50.2 (2)C5—C6—C8—N14.7 (2)
C3—C4—C5—C60.3 (2)C6—C8—N1—N2178.96 (11)
C4—C5—C6—C70.3 (2)O2—C9—N2—N1178.98 (13)
C4—C5—C6—C8178.48 (13)C10—C9—N2—N11.1 (2)
C5—C6—C7—C20.1 (2)C8—N1—N2—C9179.20 (12)
C8—C6—C7—C2178.92 (12)C3—C2—O1—C10.1 (2)
O1—C2—C7—C6179.96 (12)C7—C2—O1—C1179.27 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.042.8846 (19)169
C1—H1B···O2ii0.962.493.350 (2)148
C3—H3···Cg1iii0.932.833.544 (2)134
Symmetry codes: (i) x+1, y1, z+1; (ii) x+1, y+1, z; (iii) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H12N2O2
Mr192.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)223
a, b, c (Å)12.394 (4), 5.7278 (19), 15.017 (5)
β (°) 107.126 (4)
V3)1018.8 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.23 × 0.22 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.982, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
4871, 1768, 1502
Rint0.025
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.116, 1.07
No. of reflections1768
No. of parameters130
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.15

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.042.8846 (19)169
C1—H1B···O2ii0.962.493.350 (2)148
C3—H3···Cg1iii0.932.833.544 (2)134
Symmetry codes: (i) x+1, y1, z+1; (ii) x+1, y+1, z; (iii) x, y1/2, z+1/2.
 

Acknowledgements

The authors thank the Science and Technology Project of Zhejiang Province (grant No. 2007 F70077) and Hangzhou Vocational and Technical College for financial support.

References

First citationBruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153.  CrossRef CAS Web of Science Google Scholar
First citationLi, Y.-F. & Jian, F.-F. (2008). Acta Cryst. E64, o2409.  Web of Science CrossRef IUCr Journals Google Scholar
First citationOffe, H. A., Siefen, W. & Domagk, G. (1952). Z. Naturforsch. Teil B, 7, 446–447.  Google Scholar
First citationRichardson, 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.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTamboura, F. B., Gaye, M., Sall, A. S., Barry, A. H. & Bah, Y. (2009). Acta Cryst. E65, m160–m161.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
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