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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Jan 21;68(Pt 2):o493. doi: 10.1107/S1600536812002048

(E)-(4-Bromo­benzyl­idene)amino cyclo­propane­carboxyl­ate

Xing-Hai Liu a,b, Cheng-Xia Tan b, Jian-Quan Weng b, Hui-Jun Liu b,*
PMCID: PMC3275239  PMID: 22347095

Abstract

In the title compound, C11H10BrNO2, the dihedral angle between the benzene and cyclo­propane ring planes is 49.4 (3)°. The C—C—N—O torsion angle is −175.1 (3)°, which indicates that the C=N double bond is in the E configuration.

Related literature

For details of the synthesis, see: Liu et al. (2011a ▶). For the KARI (ketol–acid reductoisomerase) activity of related compounds, see: Liu et al. (2009a ▶,b ▶, 2010 ▶, 2011b ▶,c ▶,d ▶). For related structures, see: Liu et al. (2011a ▶,c ▶). graphic file with name e-68-0o493-scheme1.jpg

Experimental

Crystal data

  • C11H10BrNO2

  • M r = 268.11

  • Monoclinic, Inline graphic

  • a = 13.209 (3) Å

  • b = 13.789 (3) Å

  • c = 5.8714 (12) Å

  • β = 98.27 (3)°

  • V = 1058.3 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.86 mm−1

  • T = 113 K

  • 0.16 × 0.14 × 0.12 mm

Data collection

  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.577, T max = 0.654

  • 5989 measured reflections

  • 1862 independent reflections

  • 1320 reflections with I > 2σ(I)

  • R int = 0.096

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038

  • wR(F 2) = 0.082

  • S = 0.96

  • 1862 reflections

  • 136 parameters

  • H-atom parameters constrained

  • Δρmax = 0.67 e Å−3

  • Δρmin = −0.74 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002048/ds2156sup1.cif

e-68-0o493-sup1.cif (15.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002048/ds2156Isup2.hkl

e-68-0o493-Isup2.hkl (91.7KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812002048/ds2156Isup3.cml

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

Acknowledgments

This work was supported financially by the Scientific Research Fund of Zhejiang Education Department (Y201018479).

supplementary crystallographic information

Experimental

To a solution of 4-bromobenzaldehyde oxime (7.50 mmol in 25 ml THF) and 7.5 mmol Et3N, was added the cyclopropanecarbonyl chloride. Then the mixture was vigorously stirred at room temperature for overnight. The corresponding product precipitated immediately. Compound was dissolved in hot alcohol and the resulting solution was allowed to stand in air at room temperature to give single crystal.

Refinement

All the H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

Fig. 2.

Fig. 2.

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The crystal packing for (I).

Crystal data

C11H10BrNO2 F(000) = 536
Mr = 268.11 Dx = 1.683 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 2894 reflections
a = 13.209 (3) Å θ = 2.2–27.5°
b = 13.789 (3) Å µ = 3.86 mm−1
c = 5.8714 (12) Å T = 113 K
β = 98.27 (3)° Prism, colorless
V = 1058.3 (4) Å3 0.16 × 0.14 × 0.12 mm
Z = 4
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Data collection

Rigaku Saturn diffractometer 1862 independent reflections
Radiation source: rotating anode 1320 reflections with I > 2σ(I)
confocal Rint = 0.096
ω scans θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) h = −15→14
Tmin = 0.577, Tmax = 0.654 k = −15→16
5989 measured reflections l = −6→5
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082 H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0236P)2] where P = (Fo2 + 2Fc2)/3
1862 reflections (Δ/σ)max < 0.001
136 parameters Δρmax = 0.67 e Å−3
0 restraints Δρmin = −0.74 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Br1 0.63851 (3) 0.63645 (3) 1.06308 (6) 0.02820 (17)
O1 1.21657 (17) 0.58865 (18) 0.7082 (4) 0.0204 (6)
O2 1.20566 (19) 0.68074 (19) 0.3851 (4) 0.0246 (6)
N1 1.1064 (2) 0.5958 (2) 0.6861 (5) 0.0207 (7)
C1 0.9529 (3) 0.6535 (2) 1.1289 (6) 0.0183 (9)
H1 1.0055 0.6740 1.2410 0.022*
C2 0.8530 (3) 0.6600 (2) 1.1709 (6) 0.0206 (9)
H2 0.8381 0.6849 1.3094 0.025*
C3 0.7756 (3) 0.6286 (2) 1.0033 (6) 0.0181 (9)
C4 0.7967 (3) 0.5906 (3) 0.7961 (6) 0.0167 (8)
H4 0.7441 0.5693 0.6849 0.020*
C5 0.8972 (3) 0.5849 (3) 0.7583 (6) 0.0177 (8)
H5 0.9122 0.5592 0.6205 0.021*
C6 0.9762 (3) 0.6170 (2) 0.9223 (6) 0.0160 (8)
C7 1.0830 (3) 0.6136 (2) 0.8868 (6) 0.0164 (8)
H7 1.1344 0.6243 1.0100 0.020*
C8 1.2549 (3) 0.6312 (3) 0.5280 (6) 0.0187 (9)
C9 1.3629 (3) 0.6058 (3) 0.5407 (6) 0.0215 (9)
H9 1.3922 0.5636 0.6676 0.026*
C10 1.4024 (3) 0.5931 (3) 0.3108 (6) 0.0291 (10)
H10A 1.4536 0.5436 0.3005 0.035*
H10B 1.3543 0.6027 0.1714 0.035*
C11 1.4328 (3) 0.6793 (3) 0.4557 (6) 0.0287 (10)
H11A 1.4036 0.7414 0.4038 0.034*
H11B 1.5028 0.6823 0.5328 0.034*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Br1 0.0195 (3) 0.0277 (3) 0.0407 (3) 0.00510 (17) 0.0154 (2) 0.00313 (19)
O1 0.0144 (14) 0.0227 (16) 0.0259 (14) 0.0002 (12) 0.0085 (11) 0.0042 (12)
O2 0.0247 (16) 0.0239 (16) 0.0252 (14) 0.0030 (13) 0.0040 (12) 0.0030 (12)
N1 0.0111 (17) 0.026 (2) 0.0274 (17) 0.0028 (14) 0.0087 (14) −0.0021 (15)
C1 0.022 (2) 0.012 (2) 0.0204 (19) 0.0001 (16) 0.0028 (16) 0.0003 (15)
C2 0.026 (2) 0.015 (2) 0.0227 (19) 0.0055 (17) 0.0118 (17) −0.0024 (16)
C3 0.019 (2) 0.011 (2) 0.026 (2) 0.0020 (16) 0.0096 (17) 0.0032 (16)
C4 0.0088 (19) 0.013 (2) 0.028 (2) 0.0003 (16) 0.0012 (15) −0.0015 (17)
C5 0.021 (2) 0.016 (2) 0.0172 (18) 0.0015 (17) 0.0063 (16) 0.0006 (16)
C6 0.017 (2) 0.012 (2) 0.0206 (19) 0.0013 (15) 0.0054 (16) 0.0020 (15)
C7 0.012 (2) 0.012 (2) 0.025 (2) 0.0015 (15) 0.0013 (16) 0.0026 (15)
C8 0.020 (2) 0.016 (2) 0.0197 (19) −0.0078 (16) 0.0029 (17) −0.0065 (17)
C9 0.017 (2) 0.024 (2) 0.0259 (19) 0.0019 (18) 0.0098 (16) 0.0054 (17)
C10 0.023 (2) 0.035 (3) 0.032 (2) 0.001 (2) 0.0157 (18) −0.004 (2)
C11 0.020 (2) 0.036 (3) 0.032 (2) −0.009 (2) 0.0099 (18) 0.002 (2)
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Geometric parameters (Å, °)

Br1—C3 1.896 (4) C5—C6 1.386 (5)
O1—C8 1.369 (4) C5—H5 0.9300
O1—N1 1.445 (3) C6—C7 1.456 (5)
O2—C8 1.199 (4) C7—H7 0.9300
N1—C7 1.285 (4) C8—C9 1.460 (5)
C1—C2 1.379 (5) C9—C11 1.504 (5)
C1—C6 1.389 (5) C9—C10 1.525 (5)
C1—H1 0.9300 C9—H9 0.9800
C2—C3 1.383 (5) C10—C11 1.483 (5)
C2—H2 0.9300 C10—H10A 0.9700
C3—C4 1.390 (5) C10—H10B 0.9700
C4—C5 1.379 (4) C11—H11A 0.9700
C4—H4 0.9300 C11—H11B 0.9700
C8—O1—N1 112.4 (3) C6—C7—H7 119.9
C7—N1—O1 107.6 (3) O2—C8—O1 124.1 (3)
C2—C1—C6 121.2 (3) O2—C8—C9 126.9 (3)
C2—C1—H1 119.4 O1—C8—C9 109.0 (3)
C6—C1—H1 119.4 C8—C9—C11 117.6 (3)
C1—C2—C3 118.8 (3) C8—C9—C10 116.0 (3)
C1—C2—H2 120.6 C11—C9—C10 58.6 (2)
C3—C2—H2 120.6 C8—C9—H9 117.2
C2—C3—C4 121.3 (3) C11—C9—H9 117.2
C2—C3—Br1 118.6 (3) C10—C9—H9 117.2
C4—C3—Br1 120.1 (3) C11—C10—C9 60.0 (2)
C5—C4—C3 118.8 (3) C11—C10—H10A 117.8
C5—C4—H4 120.6 C9—C10—H10A 117.8
C3—C4—H4 120.6 C11—C10—H10B 117.8
C4—C5—C6 121.0 (3) C9—C10—H10B 117.8
C4—C5—H5 119.5 H10A—C10—H10B 114.9
C6—C5—H5 119.5 C10—C11—C9 61.4 (2)
C5—C6—C1 118.9 (3) C10—C11—H11A 117.6
C5—C6—C7 122.6 (3) C9—C11—H11A 117.6
C1—C6—C7 118.5 (3) C10—C11—H11B 117.6
N1—C7—C6 120.2 (3) C9—C11—H11B 117.6
N1—C7—H7 119.9 H11A—C11—H11B 114.7
C8—O1—N1—C7 −140.2 (3) O1—N1—C7—C6 −175.1 (3)
C6—C1—C2—C3 0.5 (5) C5—C6—C7—N1 11.9 (5)
C1—C2—C3—C4 0.4 (5) C1—C6—C7—N1 −168.3 (3)
C1—C2—C3—Br1 179.4 (3) N1—O1—C8—O2 10.1 (5)
C2—C3—C4—C5 −0.4 (5) N1—O1—C8—C9 −169.7 (3)
Br1—C3—C4—C5 −179.4 (3) O2—C8—C9—C11 32.6 (5)
C3—C4—C5—C6 −0.4 (5) O1—C8—C9—C11 −147.6 (3)
C4—C5—C6—C1 1.2 (5) O2—C8—C9—C10 −33.9 (5)
C4—C5—C6—C7 −179.0 (3) O1—C8—C9—C10 145.9 (3)
C2—C1—C6—C5 −1.2 (5) C8—C9—C10—C11 107.8 (4)
C2—C1—C6—C7 179.0 (3) C8—C9—C11—C10 −105.1 (4)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2156).

References

  1. Liu, X.-H., Chen, P.-Q., Wang, B.-L., Dong, W.-L., Li, Y.-H., Xie, X.-Q. & Li, Z.-M. (2010). Chem. Biol. Drug Des. 75, 228–232. [DOI] [PubMed]
  2. Liu, X.-H., Pan, L., Tan, C.-X., Weng, J.-Q., Wang, B.-L. & Li, Z.-M. (2011a). Pest. Biochem. Physiol. 101, 143–147.
  3. Liu, X.-H., Shi, Y.-X., Ma, Y., He, G.-R., Dong, W.-L., Zhang, C.-Y., Wang, B.-L., Wang, S.-H., Li, B.-J. & Li, Z.-M. (2009a). Chem. Biol. Drug Des. 73, 320–327. [DOI] [PubMed]
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  8. Rigaku/MSC (2005). CrystalClear Rigaku/MSC Inc. The Woodlands, Texas, USA.
  9. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002048/ds2156sup1.cif

e-68-0o493-sup1.cif (15.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002048/ds2156Isup2.hkl

e-68-0o493-Isup2.hkl (91.7KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812002048/ds2156Isup3.cml

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

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

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