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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2938.
Published online 2009 October 31. doi:  10.1107/S1600536809044614
PMCID: PMC2971419

Ethyl 3-[1-(4-bromo­phen­yl)eth­ylidene]carbazate

Abstract

In the crystal of the title compound, C10H11BrN2O2, the mol­ecules are linked by N—H(...)O hydrogen bonds, forming S(4) chains propagating in [100]. A C—H(...)O inter­action also occurs.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-o2938-scheme1.jpg

Experimental

Crystal data

  • C10H11BrN2O2
  • M r = 271.11
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2938-efi1.jpg
  • a = 7.6810 (15) Å
  • b = 5.9520 (12) Å
  • c = 24.750 (5) Å
  • V = 1131.5 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.62 mm−1
  • T = 293 K
  • 0.25 × 0.20 × 0.19 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: none
  • 10040 measured reflections
  • 2583 independent reflections
  • 1675 reflections with I > 2σ(I)
  • R int = 0.116

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.152
  • S = 1.02
  • 2583 reflections
  • 140 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.45 e Å−3
  • Δρmin = −0.54 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1254 Friedel pairs
  • Flack parameter: −0.008 (16)

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/S1600536809044614/hb5186sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044614/hb5186Isup2.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

Experimental

A mixture of 1-(4-bromophenyl)ethanone (0.1 mol), and methyl carbazate (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.085 mol, yield 85%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Refinement

The N-bound H atom was located in a difference map and freely refined. The other H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances=0.97 Å, and with Uiso=1.2–1.5Ueq.

Figures

Fig. 1.
The structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

C10H11BrN2O2Dx = 1.591 Mg m3
Mr = 271.11Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 1982 reflections
a = 7.6810 (15) Åθ = 3.6–27.5°
b = 5.9520 (12) ŵ = 3.62 mm1
c = 24.750 (5) ÅT = 293 K
V = 1131.5 (4) Å3Block, colourless
Z = 40.25 × 0.20 × 0.19 mm
F(000) = 544

Data collection

Bruker SMART CCD diffractometer1675 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.116
graphiteθmax = 27.5°, θmin = 3.3°
ω scansh = −9→8
10040 measured reflectionsk = −7→7
2583 independent reflectionsl = −31→32

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.152w = 1/[σ2(Fo2) + (0.068P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.054
2583 reflectionsΔρmax = 0.45 e Å3
140 parametersΔρmin = −0.54 e Å3
1 restraintAbsolute structure: Flack (1983), 1254 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.008 (16)

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
Br10.44214 (8)0.19577 (12)0.58046 (2)0.0815 (3)
C80.3535 (7)0.2162 (9)0.5091 (2)0.0584 (13)
C10.0415 (10)−0.3211 (12)0.1630 (3)0.080 (2)
H1A−0.0495−0.31710.13640.120*
H1B0.0344−0.45900.18300.120*
H1C0.1526−0.31210.14540.120*
N10.1035 (6)0.0551 (8)0.27043 (18)0.0548 (10)
C70.3861 (7)0.0435 (10)0.4736 (2)0.0600 (12)
H7A0.4517−0.07980.48450.072*
C20.1408 (6)−0.1185 (9)0.23832 (19)0.0515 (11)
O20.0223 (6)−0.1363 (9)0.19887 (18)0.0724 (12)
C90.2600 (7)0.4010 (9)0.4932 (2)0.0610 (12)
H9A0.23850.51770.51720.073*
C40.1498 (6)0.2404 (8)0.3496 (2)0.0463 (10)
C50.2249 (6)0.2378 (8)0.4043 (2)0.0470 (10)
N20.1849 (5)0.0686 (7)0.31978 (17)0.0509 (9)
C100.1984 (6)0.4113 (9)0.4408 (2)0.0542 (11)
H10A0.13740.53810.42970.065*
C60.3215 (7)0.0544 (9)0.4220 (2)0.0552 (12)
H6A0.3428−0.06370.39830.066*
O10.2632 (5)−0.2456 (6)0.24299 (17)0.0611 (9)
C30.0382 (7)0.4343 (10)0.3314 (3)0.0633 (14)
H3A0.00010.40900.29500.095*
H3B0.10470.57070.33290.095*
H3C−0.06130.44690.35470.095*
H1D0.017 (13)0.111 (17)0.276 (4)0.10 (3)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1019 (5)0.0934 (5)0.0491 (3)−0.0009 (3)−0.0070 (4)−0.0089 (4)
C80.057 (3)0.067 (3)0.051 (3)−0.003 (2)0.007 (2)−0.008 (2)
C10.099 (5)0.077 (5)0.063 (4)−0.003 (3)−0.014 (3)−0.023 (3)
N10.049 (2)0.066 (3)0.050 (2)0.004 (2)−0.0056 (19)−0.007 (2)
C70.063 (3)0.060 (3)0.057 (3)0.010 (2)−0.006 (2)−0.008 (2)
C20.050 (3)0.059 (3)0.045 (2)−0.006 (2)−0.003 (2)−0.003 (2)
O20.070 (2)0.085 (3)0.062 (3)0.011 (2)−0.024 (2)−0.020 (2)
C90.073 (3)0.055 (3)0.056 (3)0.004 (3)0.008 (2)−0.015 (3)
C40.040 (2)0.051 (2)0.049 (3)−0.0062 (19)0.0064 (19)−0.001 (2)
C50.039 (2)0.047 (2)0.055 (3)−0.0015 (18)0.0064 (19)−0.004 (2)
N20.048 (2)0.057 (2)0.047 (2)0.0031 (17)0.0013 (16)−0.002 (2)
C100.055 (3)0.045 (3)0.063 (3)0.0062 (19)0.003 (2)−0.007 (2)
C60.058 (3)0.057 (3)0.051 (3)0.009 (2)0.003 (2)−0.009 (2)
O10.055 (2)0.064 (2)0.065 (2)0.0031 (18)−0.0094 (16)−0.0121 (18)
C30.061 (3)0.058 (3)0.070 (4)0.008 (2)−0.007 (2)−0.002 (3)

Geometric parameters (Å, °)

Br1—C81.896 (6)C2—O21.339 (6)
C8—C91.372 (8)C9—C101.380 (7)
C8—C71.376 (7)C9—H9A0.9300
C1—O21.421 (8)C4—N21.289 (6)
C1—H1A0.9600C4—C51.473 (7)
C1—H1B0.9600C4—C31.507 (7)
C1—H1C0.9600C5—C101.387 (7)
N1—C21.335 (7)C5—C61.391 (7)
N1—N21.374 (6)C10—H10A0.9300
N1—H1D0.75 (10)C6—H6A0.9300
C7—C61.371 (7)C3—H3A0.9600
C7—H7A0.9300C3—H3B0.9600
C2—O11.212 (6)C3—H3C0.9600
C9—C8—C7120.7 (5)C10—C9—H9A120.5
C9—C8—Br1120.5 (4)N2—C4—C5115.8 (4)
C7—C8—Br1118.8 (4)N2—C4—C3123.8 (5)
O2—C1—H1A109.5C5—C4—C3120.4 (4)
O2—C1—H1B109.5C10—C5—C6117.2 (5)
H1A—C1—H1B109.5C10—C5—C4122.3 (4)
O2—C1—H1C109.5C6—C5—C4120.5 (4)
H1A—C1—H1C109.5C4—N2—N1117.4 (4)
H1B—C1—H1C109.5C9—C10—C5121.9 (5)
C2—N1—N2118.5 (4)C9—C10—H10A119.1
C2—N1—H1D129 (7)C5—C10—H10A119.1
N2—N1—H1D103 (7)C7—C6—C5121.6 (5)
C8—C7—C6119.6 (5)C7—C6—H6A119.2
C8—C7—H7A120.2C5—C6—H6A119.2
C6—C7—H7A120.2C4—C3—H3A109.5
O1—C2—N1126.4 (5)C4—C3—H3B109.5
O1—C2—O2123.2 (5)H3A—C3—H3B109.5
N1—C2—O2110.4 (5)C4—C3—H3C109.5
C2—O2—C1116.5 (5)H3A—C3—H3C109.5
C8—C9—C10119.0 (5)H3B—C3—H3C109.5
C8—C9—H9A120.5
C9—C8—C7—C6−1.3 (8)C3—C4—C5—C6177.1 (5)
Br1—C8—C7—C6179.3 (4)C5—C4—N2—N1173.9 (4)
N2—N1—C2—O1−15.0 (8)C3—C4—N2—N1−5.5 (7)
N2—N1—C2—O2164.9 (5)C2—N1—N2—C4178.4 (5)
O1—C2—O2—C12.8 (9)C8—C9—C10—C51.5 (8)
N1—C2—O2—C1−177.1 (6)C6—C5—C10—C9−2.0 (8)
C7—C8—C9—C100.2 (8)C4—C5—C10—C9175.8 (4)
Br1—C8—C9—C10179.5 (4)C8—C7—C6—C50.8 (8)
N2—C4—C5—C10180.0 (4)C10—C5—C6—C70.8 (7)
C3—C4—C5—C10−0.6 (7)C4—C5—C6—C7−177.0 (5)
N2—C4—C5—C6−2.3 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1D···O1i0.76 (10)2.26 (10)2.929 (6)148 (10)
C3—H3A···O1i0.962.433.242 (8)142

Symmetry codes: (i) x−1/2, −y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5186).

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.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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