organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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(E)-(2,4-Di­chloro­benzyl­­idene)amino cyclo­propane­carboxyl­ate

aCollege of Chemistry and Chemical Engineering, Beifang University of Nationalities, Yinchuan 750021, People's Republic of China
*Correspondence e-mail: aseonliu@gmail.com

(Received 10 April 2012; accepted 23 April 2012; online 2 May 2012)

In the title compound C11H9Cl2NO2, the dihedral angle between the benzene and cyclo­propane ring planes is 89.95 (13)°. The carbon­yl–oxime grouping is almost coplanar with the benzene ring [dihedral angle = 4.08 (6)°]. In the crystal, mol­ecules are linked by C—H⋯O inter­actions into [100] chains.

Related literature

For further synthetic details, see: Liu et al. (2011b[Liu, X.-H., Pan, L., Tan, C.-X., Weng, J.-Q., Wang, B.-L. & Li, Z.-M. (2011b). Pest. Biochem. Physiol. 101, 143-147.], 2012[Liu, X.-H., Tan, C.-X., Weng, J.-Q. & Liu, H.-J. (2012). Acta Cryst. E68, o493.]). For related structures, see: Liu & Liu (2011[Liu, X.-F. & Liu, X.-H. (2011). Acta Cryst. E67, o202.]) Liu et al. (2011d[Liu, H.-J., Weng, J.-Q., Tan, C.-X. & Liu, X.-H. (2011d). Acta Cryst. E67, o1940.]). For the biological activity of related compounds, see: Liu et al. (2010[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.], 2011a[Liu, X. H., Jian, Q. W. & Tan, C. X. (2011a). Asian J. Chem. 23, 4064-4066.],c[Liu, X. H., Tan, C. X. & Jian, Q. W. (2011c). Phosphorus Sulfur Silicon, 186, 552-557.]).

[Scheme 1]

Experimental

Crystal data
  • C11H9Cl2NO2

  • Mr = 258.09

  • Triclinic, [P \overline 1]

  • a = 6.4381 (13) Å

  • b = 7.6030 (15) Å

  • c = 11.956 (2) Å

  • α = 94.90 (3)°

  • β = 100.42 (3)°

  • γ = 102.70 (3)°

  • V = 556.71 (19) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.57 mm−1

  • T = 113 K

  • 0.24 × 0.20 × 0.10 mm

Data collection
  • Rigaku Saturn CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA.]) Tmin = 0.876, Tmax = 0.946

  • 3737 measured reflections

  • 1937 independent reflections

  • 1563 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.027

  • wR(F2) = 0.076

  • S = 1.03

  • 1937 reflections

  • 145 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1B⋯O1i 0.97 2.57 3.5008 (19) 161
Symmetry code: (i) x-1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Related literature top

For further synthetic details, see: Liu et al. (2011b, 2012). For related structures, see: Liu & Liu (2011) Liu et al. (2011d). For the biological activity of related compounds, see: Liu et al. (2010, 2011a,c).

Experimental top

Dropwised the cyclopropanecarbonyl chloride to 2,4-dichlorobenzaldehyde oxime (7.50 mmol in 25 ml THF) and 7.5 mmol Et3N, then vigorously stirred at ambient 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 colourless blocks of the title compound.

Refinement top

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).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: SHELXL97 (Sheldrick, 2008.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
(E)-(2,4-Dichlorobenzylidene)amino cyclopropanecarboxylate top
Crystal data top
C11H9Cl2NO2Z = 2
Mr = 258.09F(000) = 264
Triclinic, P1Dx = 1.540 Mg m3
a = 6.4381 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.6030 (15) ÅCell parameters from 1887 reflections
c = 11.956 (2) Åθ = 1.8–27.9°
α = 94.90 (3)°µ = 0.57 mm1
β = 100.42 (3)°T = 113 K
γ = 102.70 (3)°Block, coloress
V = 556.71 (19) Å30.24 × 0.20 × 0.10 mm
Data collection top
Rigaku Saturn CCD
diffractometer
1937 independent reflections
Radiation source: rotating anode1563 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.030
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
h = 77
Tmin = 0.876, Tmax = 0.946k = 96
3737 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0407P)2]
where P = (Fo2 + 2Fc2)/3
1937 reflections(Δ/σ)max = 0.001
145 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C11H9Cl2NO2γ = 102.70 (3)°
Mr = 258.09V = 556.71 (19) Å3
Triclinic, P1Z = 2
a = 6.4381 (13) ÅMo Kα radiation
b = 7.6030 (15) ŵ = 0.57 mm1
c = 11.956 (2) ÅT = 113 K
α = 94.90 (3)°0.24 × 0.20 × 0.10 mm
β = 100.42 (3)°
Data collection top
Rigaku Saturn CCD
diffractometer
1937 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
1563 reflections with I > 2σ(I)
Tmin = 0.876, Tmax = 0.946Rint = 0.030
3737 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 1.03Δρmax = 0.24 e Å3
1937 reflectionsΔρmin = 0.21 e Å3
145 parameters
Special details top

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) top
xyzUiso*/Ueq
Cl10.32359 (6)0.70035 (5)0.47089 (3)0.02317 (14)
Cl21.15092 (6)0.98054 (6)0.68823 (4)0.02531 (14)
O10.08882 (17)0.30779 (16)0.94813 (9)0.0263 (3)
O20.00692 (16)0.37138 (15)0.76492 (9)0.0186 (3)
N10.2306 (2)0.46280 (18)0.78101 (11)0.0202 (3)
C10.3868 (2)0.2548 (2)0.94150 (14)0.0217 (4)
H1A0.29710.32931.01060.026*
H1B0.53480.26890.92340.026*
C20.3504 (3)0.0724 (2)0.91336 (14)0.0208 (4)
H2A0.47640.02490.87830.025*
H2B0.23880.03540.96550.025*
C30.2777 (2)0.2198 (2)0.84222 (14)0.0198 (4)
H30.36290.21130.76440.024*
C40.0426 (2)0.3004 (2)0.86199 (13)0.0177 (4)
C50.2637 (2)0.5304 (2)0.69054 (14)0.0177 (4)
H50.15110.51290.62680.021*
C60.4823 (2)0.6365 (2)0.68810 (14)0.0164 (4)
C70.5265 (3)0.7218 (2)0.59348 (13)0.0168 (4)
C80.7305 (2)0.8271 (2)0.59131 (13)0.0188 (4)
H80.75660.88360.52750.023*
C90.8947 (2)0.8453 (2)0.68750 (14)0.0187 (4)
C100.8595 (3)0.7612 (2)0.78232 (14)0.0196 (4)
H100.97250.77360.84530.024*
C110.6539 (2)0.6579 (2)0.78256 (14)0.0177 (4)
H110.62930.60160.84660.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0227 (2)0.0314 (3)0.0143 (2)0.00420 (18)0.00140 (17)0.00786 (18)
Cl20.0192 (2)0.0275 (2)0.0273 (3)0.00120 (17)0.00716 (17)0.00581 (18)
O10.0182 (6)0.0425 (8)0.0166 (7)0.0021 (5)0.0021 (5)0.0121 (6)
O20.0123 (5)0.0267 (6)0.0165 (6)0.0012 (5)0.0038 (4)0.0082 (5)
N10.0117 (6)0.0267 (8)0.0213 (8)0.0005 (6)0.0039 (5)0.0072 (6)
C10.0179 (8)0.0266 (9)0.0221 (10)0.0051 (7)0.0073 (7)0.0061 (7)
C20.0191 (8)0.0226 (9)0.0198 (9)0.0004 (7)0.0059 (7)0.0054 (7)
C30.0151 (8)0.0264 (9)0.0160 (9)0.0002 (7)0.0027 (7)0.0059 (7)
C40.0187 (8)0.0201 (8)0.0162 (9)0.0045 (7)0.0070 (7)0.0059 (7)
C50.0178 (8)0.0218 (9)0.0145 (9)0.0048 (7)0.0041 (7)0.0056 (7)
C60.0184 (8)0.0158 (8)0.0162 (9)0.0042 (6)0.0061 (7)0.0031 (6)
C70.0185 (8)0.0193 (8)0.0134 (9)0.0070 (6)0.0019 (6)0.0024 (6)
C80.0244 (9)0.0189 (9)0.0165 (10)0.0057 (7)0.0100 (7)0.0071 (7)
C90.0181 (8)0.0170 (8)0.0223 (9)0.0038 (7)0.0082 (7)0.0024 (7)
C100.0189 (8)0.0226 (9)0.0183 (9)0.0077 (7)0.0022 (7)0.0040 (7)
C110.0194 (8)0.0206 (9)0.0166 (9)0.0079 (7)0.0065 (7)0.0073 (7)
Geometric parameters (Å, º) top
Cl1—C71.7477 (16)C3—C41.470 (2)
Cl2—C91.7394 (16)C3—H30.9800
O1—C41.1976 (18)C5—C61.467 (2)
O2—C41.3800 (19)C5—H50.9300
O2—N11.4253 (16)C6—C71.394 (2)
N1—C51.269 (2)C6—C111.401 (2)
C1—C21.478 (2)C7—C81.385 (2)
C1—C31.517 (2)C8—C91.389 (2)
C1—H1A0.9700C8—H80.9300
C1—H1B0.9700C9—C101.378 (2)
C2—C31.508 (2)C10—C111.383 (2)
C2—H2A0.9700C10—H100.9300
C2—H2B0.9700C11—H110.9300
C4—O2—N1112.18 (11)O2—C4—C3109.31 (12)
C5—N1—O2109.05 (12)N1—C5—C6118.94 (14)
C2—C1—C360.45 (11)N1—C5—H5120.5
C2—C1—H1A117.7C6—C5—H5120.5
C3—C1—H1A117.7C7—C6—C11117.60 (14)
C2—C1—H1B117.7C7—C6—C5121.71 (14)
C3—C1—H1B117.7C11—C6—C5120.69 (15)
H1A—C1—H1B114.8C8—C7—C6122.37 (14)
C1—C2—C361.08 (11)C8—C7—Cl1116.74 (13)
C1—C2—H2A117.7C6—C7—Cl1120.89 (12)
C3—C2—H2A117.7C7—C8—C9117.79 (15)
C1—C2—H2B117.7C7—C8—H8121.1
C3—C2—H2B117.7C9—C8—H8121.1
H2A—C2—H2B114.8C10—C9—C8121.89 (15)
C4—C3—C2116.62 (14)C10—C9—Cl2119.36 (12)
C4—C3—C1115.92 (13)C8—C9—Cl2118.75 (13)
C2—C3—C158.47 (11)C9—C10—C11119.14 (14)
C4—C3—H3117.5C9—C10—H10120.4
C2—C3—H3117.5C11—C10—H10120.4
C1—C3—H3117.5C10—C11—C6121.20 (15)
O1—C4—O2123.97 (14)C10—C11—H11119.4
O1—C4—C3126.72 (15)C6—C11—H11119.4
C4—O2—N1—C5177.60 (13)C5—C6—C7—C8177.96 (16)
C1—C2—C3—C4105.44 (16)C11—C6—C7—Cl1179.11 (13)
C2—C1—C3—C4106.64 (16)C5—C6—C7—Cl12.0 (2)
N1—O2—C4—O13.1 (2)C6—C7—C8—C90.4 (3)
N1—O2—C4—C3176.04 (13)Cl1—C7—C8—C9179.65 (12)
C2—C3—C4—O125.6 (3)C7—C8—C9—C100.6 (3)
C1—C3—C4—O140.4 (2)C7—C8—C9—Cl2178.69 (13)
C2—C3—C4—O2155.33 (15)C8—C9—C10—C111.1 (3)
C1—C3—C4—O2138.66 (14)Cl2—C9—C10—C11178.24 (13)
O2—N1—C5—C6178.12 (13)C9—C10—C11—C60.5 (3)
N1—C5—C6—C7176.72 (16)C7—C6—C11—C100.5 (2)
N1—C5—C6—C112.2 (3)C5—C6—C11—C10178.44 (16)
C11—C6—C7—C81.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O1i0.972.573.5008 (19)161
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC11H9Cl2NO2
Mr258.09
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)6.4381 (13), 7.6030 (15), 11.956 (2)
α, β, γ (°)94.90 (3), 100.42 (3), 102.70 (3)
V3)556.71 (19)
Z2
Radiation typeMo Kα
µ (mm1)0.57
Crystal size (mm)0.24 × 0.20 × 0.10
Data collection
DiffractometerRigaku Saturn CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.876, 0.946
No. of measured, independent and
observed [I > 2σ(I)] reflections
3737, 1937, 1563
Rint0.030
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.076, 1.03
No. of reflections1937
No. of parameters145
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.21

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O1i0.972.573.5008 (19)161
Symmetry code: (i) x1, y, z.
 

Acknowledgements

This research work was supported by the Research Program of Beifang University of Nationalities (2010Y047) and the Key Laboratory of Chemical Technology of the SEAC (2010SY16).

References

First citationLiu, 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.  Web of Science CrossRef CAS PubMed Google Scholar
First citationLiu, X. H., Jian, Q. W. & Tan, C. X. (2011a). Asian J. Chem. 23, 4064–4066.  CAS Google Scholar
First citationLiu, X.-F. & Liu, X.-H. (2011). Acta Cryst. E67, o202.  Web of Science CrossRef IUCr Journals Google Scholar
First citationLiu, X.-H., Pan, L., Tan, C.-X., Weng, J.-Q., Wang, B.-L. & Li, Z.-M. (2011b). Pest. Biochem. Physiol. 101, 143–147.  Web of Science CrossRef CAS Google Scholar
First citationLiu, X. H., Tan, C. X. & Jian, Q. W. (2011c). Phosphorus Sulfur Silicon, 186, 552–557.  Web of Science CrossRef CAS Google Scholar
First citationLiu, X.-H., Tan, C.-X., Weng, J.-Q. & Liu, H.-J. (2012). Acta Cryst. E68, o493.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLiu, H.-J., Weng, J.-Q., Tan, C.-X. & Liu, X.-H. (2011d). Acta Cryst. E67, o1940.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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