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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1429.
Published online 2010 May 22. doi:  10.1107/S160053681001799X
PMCID: PMC2979553

Methyl 3-(4-methyl­benzyl­idene)carbazate

Abstract

The title compound, C10H12N2O2, was prepared by the reaction of methyl carbazate and 4-methyl­benzaldehyde. The dihedral angle between the benzene ring and the carbazate fragment is 20.86 (10)°. In the crystal structure, mol­ecules are linked by inter­molecular N—H(...)O hydrogen bonds.

Related literature

For background to Schiff bases, see: Cimerman et al. (1997 [triangle]). For C=N bond lengths, see: Girgis (2006 [triangle]). For a related structure, see: Li et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1429-scheme1.jpg

Experimental

Crystal data

  • C10H12N2O2
  • M r = 192.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1429-efi1.jpg
  • a = 10.038 (2) Å
  • b = 13.308 (3) Å
  • c = 7.7923 (16) Å
  • β = 99.71 (3)°
  • V = 1026.1 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.22 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • 9493 measured reflections
  • 2322 independent reflections
  • 1528 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.175
  • S = 1.06
  • 2322 reflections
  • 127 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.23 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/S160053681001799X/hg2684sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001799X/hg2684Isup2.hkl

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

supplementary crystallographic information

Comment

Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman, et al., 1997). As part of our search for new Schiff base compounds we synthesized the title compound (I), and describe its structure here.

The molcular structure of (I) is shown in Fig. 1. The C8—N2 bond length of 1.273 (2)Å is comparable with C—N double bond [1.281 (2) Å] reported (Girgis, 2006). In the crystal structure, molecules are linked by intermolecular N—H···O hydrogen bonds.

Experimental

A mixture of methyl carbazate (0.1 mol), and 4-methylbenzaldehyde (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.085 mol, yield 85%). Single crystals suitable for X-ray measurements 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 distances = 0.93-0.97 Å; N—H = 0.86Å and with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(Cmethyl).

Figures

Fig. 1.
The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C10H12N2O2F(000) = 408
Mr = 192.22Dx = 1.244 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1798 reflections
a = 10.038 (2) Åθ = 3.5–25.2°
b = 13.308 (3) ŵ = 0.09 mm1
c = 7.7923 (16) ÅT = 293 K
β = 99.71 (3)°Blcok, colorless
V = 1026.1 (4) Å30.22 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1528 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
graphiteθmax = 27.5°, θmin = 3.1°
phi and ω scansh = −13→12
9493 measured reflectionsk = −17→17
2322 independent reflectionsl = −9→10

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.1077P)2] where P = (Fo2 + 2Fc2)/3
2322 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.23 e Å3

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, 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
O20.44060 (12)0.82548 (9)0.19195 (16)0.0656 (4)
C90.55062 (16)0.81674 (12)0.1159 (2)0.0531 (4)
N20.75692 (13)0.73089 (10)0.14969 (17)0.0559 (4)
O10.56744 (12)0.86340 (9)−0.01208 (15)0.0636 (4)
C50.95735 (16)0.62998 (12)0.1941 (2)0.0540 (4)
N10.63541 (14)0.74964 (11)0.20247 (18)0.0617 (4)
H1A0.61410.71840.29060.074*
C80.82561 (17)0.66004 (13)0.2311 (2)0.0580 (4)
H8A0.79030.62610.31760.070*
C31.15344 (17)0.65532 (14)0.0599 (2)0.0661 (5)
H3A1.20040.6951−0.00780.079*
C21.20961 (17)0.56483 (14)0.1252 (2)0.0623 (5)
C71.13692 (18)0.50763 (15)0.2245 (2)0.0683 (5)
H7A1.17190.44650.26920.082*
C61.01357 (17)0.53927 (13)0.2585 (2)0.0629 (5)
H6A0.96680.49920.32600.076*
C41.02987 (18)0.68754 (13)0.0931 (2)0.0647 (5)
H4A0.99470.74840.04750.078*
C100.3380 (2)0.89244 (15)0.1047 (3)0.0789 (6)
H10A0.26300.89380.16650.118*
H10B0.30800.8693−0.01200.118*
H10C0.37490.95890.10170.118*
C11.3469 (2)0.53239 (18)0.0914 (3)0.0857 (6)
H1B1.36990.46870.14630.128*
H1C1.41310.58150.13830.128*
H1D1.34490.5263−0.03170.128*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O20.0612 (7)0.0707 (8)0.0700 (8)0.0078 (5)0.0254 (6)0.0082 (6)
C90.0607 (10)0.0489 (8)0.0527 (9)−0.0029 (7)0.0181 (8)−0.0056 (7)
N20.0573 (8)0.0566 (8)0.0561 (8)0.0004 (6)0.0165 (6)−0.0012 (6)
O10.0813 (9)0.0577 (7)0.0566 (7)0.0059 (6)0.0251 (6)0.0061 (5)
C50.0561 (9)0.0530 (9)0.0517 (9)−0.0046 (7)0.0059 (7)−0.0048 (7)
N10.0632 (9)0.0686 (9)0.0580 (9)0.0076 (7)0.0241 (7)0.0119 (7)
C80.0613 (10)0.0600 (10)0.0535 (9)−0.0063 (8)0.0121 (8)0.0016 (7)
C30.0633 (10)0.0656 (11)0.0719 (12)−0.0027 (8)0.0187 (9)0.0010 (8)
C20.0575 (9)0.0670 (11)0.0597 (10)0.0026 (8)0.0025 (8)−0.0105 (8)
C70.0672 (11)0.0635 (11)0.0698 (11)0.0086 (8)−0.0011 (9)0.0068 (8)
C60.0629 (10)0.0635 (10)0.0606 (10)−0.0035 (8)0.0052 (8)0.0096 (8)
C40.0675 (11)0.0547 (9)0.0736 (12)0.0034 (8)0.0169 (9)0.0050 (8)
C100.0678 (12)0.0721 (12)0.0987 (15)0.0134 (9)0.0196 (11)0.0115 (11)
C10.0677 (12)0.1015 (15)0.0883 (14)0.0137 (11)0.0145 (10)−0.0081 (12)

Geometric parameters (Å, °)

O2—C91.343 (2)C3—H3A0.9300
O2—C101.442 (2)C2—C71.379 (3)
C9—O11.2108 (19)C2—C11.509 (3)
C9—N11.335 (2)C7—C61.375 (2)
N2—C81.273 (2)C7—H7A0.9300
N2—N11.3742 (19)C6—H6A0.9300
C5—C41.389 (2)C4—H4A0.9300
C5—C61.390 (2)C10—H10A0.9600
C5—C81.456 (2)C10—H10B0.9600
N1—H1A0.8600C10—H10C0.9600
C8—H8A0.9300C1—H1B0.9600
C3—C41.378 (2)C1—H1C0.9600
C3—C21.389 (3)C1—H1D0.9600
C9—O2—C10114.86 (13)C6—C7—H7A119.4
O1—C9—N1126.40 (15)C2—C7—H7A119.4
O1—C9—O2123.93 (15)C7—C6—C5121.34 (17)
N1—C9—O2109.67 (14)C7—C6—H6A119.3
C8—N2—N1114.77 (14)C5—C6—H6A119.3
C4—C5—C6117.63 (16)C3—C4—C5120.62 (17)
C4—C5—C8122.74 (16)C3—C4—H4A119.7
C6—C5—C8119.61 (16)C5—C4—H4A119.7
C9—N1—N2119.52 (13)O2—C10—H10A109.5
C9—N1—H1A120.2O2—C10—H10B109.5
N2—N1—H1A120.2H10A—C10—H10B109.5
N2—C8—C5122.59 (16)O2—C10—H10C109.5
N2—C8—H8A118.7H10A—C10—H10C109.5
C5—C8—H8A118.7H10B—C10—H10C109.5
C4—C3—C2121.59 (17)C2—C1—H1B109.5
C4—C3—H3A119.2C2—C1—H1C109.5
C2—C3—H3A119.2H1B—C1—H1C109.5
C7—C2—C3117.61 (17)C2—C1—H1D109.5
C7—C2—C1121.67 (17)H1B—C1—H1D109.5
C3—C2—C1120.70 (18)H1C—C1—H1D109.5
C6—C7—C2121.21 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.002.8615 (18)176

Symmetry codes: (i) x, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2684).

References

  • Bruker (1997). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153.
  • Girgis, A. S. (2006). J. Chem. Res. pp. 81–85.
  • Li, Y.-F., Liu, H.-X. & Jian, F.-F. (2009). Acta Cryst. E65, o2959. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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