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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2919.
Published online 2009 October 31. doi:  10.1107/S1600536809044420
PMCID: PMC2971455

Ethyl 3-(2,4-dichloro­benzyl­idene)carbazate

Abstract

The title compound, C10H10Cl2N2O2, was prepared by the reaction of ethyl carbazate and 2,4-dichloro­benzaldehyde. In the crystal structure, mol­ecules are linked by inter­molecular N—H(...)O hydrogen bonds, forming extended chains along [001].

Related literature

For applications of Schiff base compounds, see: Cimerman et al. (1997 [triangle]). For the C=N double-bond length in a related structure, see: Girgis (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2919-scheme1.jpg

Experimental

Crystal data

  • C10H10Cl2N2O2
  • M r = 261.10
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-65-o2919-efi1.jpg
  • a = 18.021 (3) Å
  • c = 14.983 (3) Å
  • V = 4865.8 (14) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.52 mm−1
  • T = 293 K
  • 0.25 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.492, T max = 0.729
  • 21376 measured reflections
  • 2789 independent reflections
  • 2409 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.121
  • S = 1.09
  • 2789 reflections
  • 146 parameters
  • H-atom parameters constrained
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.50 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/S1600536809044420/lh2929sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044420/lh2929Isup2.hkl

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

Acknowledgments

The authors would like to thank the Science Foundation of WeiFang University (No. 2009Z24).

supplementary crystallographic information

Comment

Schiff bases have received considerable attention in the literature and have potential analytical applications (Cimerman et al., 1997). As part of our search for new schiff base compounds we synthesized the title compound (I), and its crystal structure is determined herein.

The molcular structure of (I) is shown in Fig. 1. The C8—N1 bond length of 1.271 (2)Å is comparable with C—N double bond [1.281 (2) Å] reported in a related structure (Girgis, 2006). In the crystal structure, molecules are linked by intermolecular N-H···O hydrogen bonds to form extended chains along [001].

Experimental

A mixture of the 2,4-dichlorobenzaldehyde (0.1 mol), and Ethyl carbazate (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.080 mol, yield 80%). Single crystals suitable for X-ray measurements were obtained by recrystallization of a solution of (I) in 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 molecular structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C10H10Cl2N2O2Dx = 1.426 Mg m3
Mr = 261.10Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 1977 reflections
Hall symbol: -I 4adθ = 3.5–27.4°
a = 18.021 (3) ŵ = 0.52 mm1
c = 14.983 (3) ÅT = 293 K
V = 4865.8 (14) Å3Block, colorless
Z = 160.25 × 0.20 × 0.18 mm
F(000) = 2144

Data collection

Bruker SMART CCD diffractometer2789 independent reflections
Radiation source: fine-focus sealed tube2409 reflections with I > 2σ(I)
graphiteRint = 0.045
[var phi] and ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −23→23
Tmin = 0.492, Tmax = 0.729k = −23→23
21376 measured reflectionsl = −19→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.121w = 1/[σ2(Fo2) + (0.0645P)2 + 2.5907P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
2789 reflectionsΔρmax = 0.37 e Å3
146 parametersΔρmin = −0.49 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: 0.0030 (4)

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
Cl10.22311 (4)0.76326 (3)0.01502 (4)0.0730 (2)
Cl20.09897 (3)0.79872 (3)−0.30581 (4)0.0661 (2)
N20.28329 (7)0.54137 (8)−0.06890 (9)0.0376 (3)
O20.39424 (7)0.41332 (7)0.04214 (8)0.0474 (3)
N10.32058 (8)0.50259 (8)−0.00379 (9)0.0416 (3)
H1A0.32280.51890.05010.050*
O10.34815 (8)0.40718 (7)−0.09813 (8)0.0500 (3)
C80.35371 (9)0.43809 (9)−0.02677 (10)0.0362 (3)
C70.26094 (9)0.60548 (10)−0.04588 (11)0.0411 (4)
H7A0.26950.62240.01190.049*
C40.22188 (8)0.65273 (9)−0.10968 (10)0.0371 (3)
C20.16741 (10)0.67119 (10)−0.25620 (11)0.0440 (4)
H2B0.15680.6534−0.31300.053*
C50.20078 (10)0.72492 (10)−0.08829 (11)0.0441 (4)
C30.20456 (10)0.62758 (9)−0.19537 (11)0.0414 (4)
H3A0.21860.5798−0.21190.050*
C10.14623 (10)0.74200 (10)−0.23128 (12)0.0445 (4)
C60.16227 (11)0.76940 (10)−0.14764 (13)0.0498 (4)
H6A0.14750.8170−0.13140.060*
C90.44238 (11)0.35079 (11)0.02348 (14)0.0538 (5)
H9A0.41730.3167−0.01660.065*
H9B0.45290.32460.07860.065*
C100.51290 (15)0.37543 (18)−0.0177 (2)0.0908 (9)
H10A0.54360.3330−0.02970.136*
H10B0.53830.40830.02250.136*
H10C0.50250.4010−0.07250.136*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1010 (5)0.0595 (3)0.0586 (3)0.0176 (3)−0.0303 (3)−0.0252 (2)
Cl20.0726 (4)0.0565 (3)0.0693 (4)0.0135 (2)−0.0261 (3)0.0084 (2)
N20.0396 (7)0.0420 (7)0.0312 (6)0.0035 (6)−0.0042 (5)0.0013 (5)
O20.0540 (7)0.0566 (7)0.0316 (6)0.0170 (6)−0.0047 (5)0.0045 (5)
N10.0505 (8)0.0476 (8)0.0266 (6)0.0112 (6)−0.0060 (5)−0.0019 (5)
O10.0713 (8)0.0455 (6)0.0332 (6)0.0116 (6)−0.0084 (6)−0.0044 (5)
C80.0401 (8)0.0411 (8)0.0275 (7)0.0010 (6)−0.0002 (6)0.0048 (6)
C70.0445 (8)0.0457 (9)0.0332 (7)0.0056 (7)−0.0035 (6)−0.0033 (7)
C40.0351 (7)0.0399 (8)0.0361 (8)0.0016 (6)−0.0014 (6)−0.0019 (6)
C20.0458 (9)0.0494 (9)0.0367 (8)0.0031 (7)−0.0066 (7)−0.0039 (7)
C50.0477 (9)0.0423 (8)0.0423 (9)0.0029 (7)−0.0076 (7)−0.0086 (7)
C30.0451 (9)0.0403 (8)0.0388 (8)0.0063 (7)−0.0026 (7)−0.0048 (7)
C10.0418 (9)0.0437 (9)0.0481 (9)0.0038 (7)−0.0090 (7)0.0051 (7)
C60.0548 (10)0.0383 (8)0.0562 (11)0.0077 (7)−0.0096 (9)−0.0067 (8)
C90.0595 (11)0.0533 (10)0.0484 (10)0.0185 (9)0.0017 (9)0.0126 (8)
C100.0688 (15)0.106 (2)0.098 (2)0.0277 (14)0.0305 (14)0.0353 (17)

Geometric parameters (Å, °)

Cl1—C51.7421 (17)C2—C31.377 (2)
Cl2—C11.7370 (17)C2—C11.383 (2)
N2—C71.271 (2)C2—H2B0.9300
N2—N11.3755 (18)C5—C61.384 (2)
O2—C81.3412 (19)C3—H3A0.9300
O2—C91.449 (2)C1—C61.378 (3)
N1—C81.351 (2)C6—H6A0.9300
N1—H1A0.8600C9—C101.481 (3)
O1—C81.2097 (19)C9—H9A0.9700
C7—C41.461 (2)C9—H9B0.9700
C7—H7A0.9300C10—H10A0.9600
C4—C51.393 (2)C10—H10B0.9600
C4—C31.397 (2)C10—H10C0.9600
C7—N2—N1115.10 (13)C2—C3—H3A118.9
C8—O2—C9115.87 (14)C4—C3—H3A118.9
C8—N1—N2118.18 (13)C6—C1—C2121.22 (16)
C8—N1—H1A120.9C6—C1—Cl2118.48 (13)
N2—N1—H1A120.9C2—C1—Cl2120.30 (14)
O1—C8—O2124.90 (15)C1—C6—C5118.83 (16)
O1—C8—N1125.78 (15)C1—C6—H6A120.6
O2—C8—N1109.31 (13)C5—C6—H6A120.6
N2—C7—C4120.32 (14)O2—C9—C10111.15 (19)
N2—C7—H7A119.8O2—C9—H9A109.4
C4—C7—H7A119.8C10—C9—H9A109.4
C5—C4—C3116.98 (15)O2—C9—H9B109.4
C5—C4—C7121.69 (14)C10—C9—H9B109.4
C3—C4—C7121.33 (14)H9A—C9—H9B108.0
C3—C2—C1118.81 (16)C9—C10—H10A109.5
C3—C2—H2B120.6C9—C10—H10B109.5
C1—C2—H2B120.6H10A—C10—H10B109.5
C6—C5—C4122.01 (15)C9—C10—H10C109.5
C6—C5—Cl1117.20 (13)H10A—C10—H10C109.5
C4—C5—Cl1120.79 (13)H10B—C10—H10C109.5
C2—C3—C4122.12 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.122.927 (2)156

Symmetry codes: (i) −y+3/4, x+1/4, z+1/4.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2929).

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.
  • Girgis, A. S. (2006). J. Chem. Res.2, 81–83.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • 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