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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2963.
Published online 2009 October 31. doi:  10.1107/S1600536809045012
PMCID: PMC2970978

Methyl 3-benzyl­idenecarbazate

Abstract

In the crystal of the title compound, C9H10N2O2, the mol­ecules are linked by N—H(...)O hydrogen bonds, generating S(4) chains propagating in [010].

Related literature

For background to Schiff bases, see: Cimerman et al. (1997 [triangle]).

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Object name is e-65-o2963-scheme1.jpg

Experimental

Crystal data

  • C9H10N2O2
  • M r = 178.19
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2963-efi1.jpg
  • a = 12.278 (3) Å
  • b = 7.8035 (16) Å
  • c = 19.466 (4) Å
  • V = 1865.1 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.25 × 0.21 × 0.19 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 16349 measured reflections
  • 2132 independent reflections
  • 1693 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.147
  • S = 1.08
  • 2132 reflections
  • 119 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045012/hb5195sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045012/hb5195Isup2.hkl

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

Acknowledgments

The authors thank the Science Foundation of Weifang University (No. 2009Z24).

supplementary crystallographic information

Experimental

A mixture of benzaldehyde (0.1 mol), and methyl carbazate (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.089 mol, yield 89%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H = 0.97 Å, and with Uiso = 1.2–1.5Ueq.

Figures

Fig. 1.
The structure of the title compound showing 30% probability displacement ellipsoids.

Crystal data

C9H10N2O2F(000) = 752
Mr = 178.19Dx = 1.269 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1984 reflections
a = 12.278 (3) Åθ = 3.5–27.5°
b = 7.8035 (16) ŵ = 0.09 mm1
c = 19.466 (4) ÅT = 293 K
V = 1865.1 (7) Å3Block, colourless
Z = 80.25 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer1693 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
graphiteθmax = 27.5°, θmin = 3.3°
[var phi] and ω scansh = −15→15
16349 measured reflectionsk = −10→8
2132 independent reflectionsl = −25→25

Refinement

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) = 0.147w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
2132 reflectionsΔρmax = 0.23 e Å3
119 parametersΔρmin = −0.18 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: 0.011 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O20.87392 (7)0.13497 (11)0.52542 (4)0.0522 (3)
N20.72993 (8)0.24691 (12)0.62265 (4)0.0434 (3)
O10.85158 (9)0.38853 (12)0.47171 (5)0.0613 (3)
C30.65739 (9)0.31376 (15)0.66062 (6)0.0443 (3)
H3A0.61840.40770.64450.053*
N10.74972 (9)0.33172 (13)0.56166 (5)0.0505 (3)
H1A0.71250.42070.55040.061*
C40.63373 (10)0.24621 (14)0.72925 (5)0.0418 (3)
C20.82860 (10)0.27174 (15)0.52044 (5)0.0434 (3)
C90.70485 (10)0.13562 (16)0.76285 (6)0.0508 (3)
H9A0.76780.09860.74080.061*
C70.58904 (13)0.13493 (19)0.86228 (7)0.0599 (4)
H7A0.57470.09880.90690.072*
C50.54021 (11)0.29976 (18)0.76341 (6)0.0532 (3)
H5A0.49220.37470.74190.064*
C80.68246 (13)0.08046 (19)0.82877 (6)0.0596 (4)
H8A0.73040.00630.85080.072*
C60.51809 (12)0.24207 (18)0.82934 (7)0.0607 (4)
H6A0.45450.27650.85130.073*
C10.93760 (15)0.3429 (2)0.42527 (8)0.0764 (5)
H1B0.94840.43380.39280.115*
H1C0.91840.23970.40130.115*
H1D1.00360.32460.45070.115*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O20.0572 (6)0.0453 (5)0.0541 (5)0.0041 (4)0.0082 (4)0.0034 (3)
N20.0465 (6)0.0427 (6)0.0410 (5)0.0010 (4)0.0018 (4)0.0047 (4)
O10.0771 (7)0.0523 (6)0.0546 (5)0.0022 (5)0.0182 (4)0.0139 (4)
C30.0451 (6)0.0414 (6)0.0464 (6)0.0032 (5)−0.0009 (4)0.0013 (5)
N10.0609 (6)0.0439 (6)0.0467 (6)0.0103 (4)0.0078 (4)0.0111 (4)
C40.0426 (6)0.0396 (6)0.0431 (6)−0.0032 (4)0.0012 (4)−0.0018 (5)
C20.0485 (7)0.0411 (6)0.0406 (6)−0.0053 (5)−0.0008 (4)0.0020 (4)
C90.0478 (7)0.0529 (7)0.0517 (7)0.0042 (5)0.0020 (5)0.0018 (5)
C70.0777 (9)0.0568 (8)0.0452 (7)−0.0139 (7)0.0074 (6)−0.0002 (5)
C50.0488 (7)0.0525 (7)0.0584 (7)0.0036 (5)0.0066 (5)0.0004 (5)
C80.0678 (9)0.0585 (8)0.0526 (7)−0.0012 (6)−0.0053 (6)0.0085 (5)
C60.0614 (8)0.0595 (8)0.0613 (8)−0.0038 (6)0.0204 (6)−0.0057 (6)
C10.0882 (11)0.0756 (10)0.0652 (9)−0.0041 (8)0.0305 (8)0.0085 (8)

Geometric parameters (Å, °)

O2—C21.2075 (15)C9—H9A0.9300
N2—C31.2694 (15)C7—C61.367 (2)
N2—N11.3808 (13)C7—C81.386 (2)
O1—C21.3453 (14)C7—H7A0.9300
O1—C11.4351 (18)C5—C61.3868 (17)
C3—C41.4653 (16)C5—H5A0.9300
C3—H3A0.9300C8—H8A0.9300
N1—C21.3420 (16)C6—H6A0.9300
N1—H1A0.8600C1—H1B0.9600
C4—C91.3911 (18)C1—H1C0.9600
C4—C51.3912 (17)C1—H1D0.9600
C9—C81.3811 (18)
C3—N2—N1115.28 (10)C6—C7—H7A120.2
C2—O1—C1115.48 (11)C8—C7—H7A120.2
N2—C3—C4121.47 (11)C6—C5—C4120.43 (13)
N2—C3—H3A119.3C6—C5—H5A119.8
C4—C3—H3A119.3C4—C5—H5A119.8
C2—N1—N2118.29 (10)C9—C8—C7120.42 (13)
C2—N1—H1A120.9C9—C8—H8A119.8
N2—N1—H1A120.9C7—C8—H8A119.8
C9—C4—C5118.66 (11)C7—C6—C5120.52 (13)
C9—C4—C3121.84 (11)C7—C6—H6A119.7
C5—C4—C3119.43 (11)C5—C6—H6A119.7
O2—C2—N1126.35 (10)O1—C1—H1B109.5
O2—C2—O1123.97 (11)O1—C1—H1C109.5
N1—C2—O1109.67 (10)H1B—C1—H1C109.5
C8—C9—C4120.35 (12)O1—C1—H1D109.5
C8—C9—H9A119.8H1B—C1—H1D109.5
C4—C9—H9A119.8H1C—C1—H1D109.5
C6—C7—C8119.60 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.042.8986 (15)179

Symmetry codes: (i) −x+3/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5195).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography