Literature DB >> 22719402

(E)-(2,4-Dichloro-benzyl-idene)amino cyclo-propane-carboxyl-ate.

Abstract

In the title compound C(11)H(9)Cl(2)NO(2), the dihedral angle between the benzene and cyclo-propane ring planes is 89.95 (13)°. The carbon-yl-oxime grouping is almost coplanar with the benzene ring [dihedral angle = 4.08 (6)°]. In the crystal, mol-ecules are linked by C-H⋯O inter-actions into [100] chains.

Entities: Chemical Disease Gene

Year: 2012 PMID： 22719402 PMCID： PMC3379204 DOI： 10.1107/S1600536812018016

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

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

Crystal data

C11H9Cl2NO2 M = 258.09 Triclinic, 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 ▶) T min = 0.876, T max = 0.946 3737 measured reflections 1937 independent reflections 1563 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.027 wR(F 2) = 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 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: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018016/hb6735sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018016/hb6735Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812018016/hb6735Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₁H₉Cl₂NO₂	Z = 2
M_r = 258.09	F(000) = 264
Triclinic, P1	D_x = 1.540 Mg m⁻³
a = 6.4381 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6030 (15) Å	Cell parameters from 1887 reflections
c = 11.956 (2) Å	θ = 1.8–27.9°
α = 94.90 (3)°	µ = 0.57 mm⁻¹
β = 100.42 (3)°	T = 113 K
γ = 102.70 (3)°	Block, coloress
V = 556.71 (19) Å³	0.24 × 0.20 × 0.10 mm

Rigaku Saturn CCD diffractometer	1937 independent reflections
Radiation source: rotating anode	1563 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.030
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −7→7
T_min = 0.876, T_max = 0.946	k = −9→6
3737 measured reflections	l = −14→14

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0407P)²] where P = (F_o² + 2F_c²)/3
1937 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
Cl1	0.32359 (6)	0.70035 (5)	0.47089 (3)	0.02317 (14)
Cl2	1.15092 (6)	0.98054 (6)	0.68823 (4)	0.02531 (14)
O1	0.08882 (17)	0.30779 (16)	0.94813 (9)	0.0263 (3)
O2	0.00692 (16)	0.37138 (15)	0.76492 (9)	0.0186 (3)
N1	0.2306 (2)	0.46280 (18)	0.78101 (11)	0.0202 (3)
C1	−0.3868 (2)	0.2548 (2)	0.94150 (14)	0.0217 (4)
H1A	−0.2971	0.3293	1.0106	0.026*
H1B	−0.5348	0.2689	0.9234	0.026*
C2	−0.3504 (3)	0.0724 (2)	0.91336 (14)	0.0208 (4)
H2A	−0.4764	−0.0249	0.8783	0.025*
H2B	−0.2388	0.0354	0.9655	0.025*
C3	−0.2777 (2)	0.2198 (2)	0.84222 (14)	0.0198 (4)
H3	−0.3629	0.2113	0.7644	0.024*
C4	−0.0426 (2)	0.3004 (2)	0.86199 (13)	0.0177 (4)
C5	0.2637 (2)	0.5304 (2)	0.69054 (14)	0.0177 (4)
H5	0.1511	0.5129	0.6268	0.021*
C6	0.4823 (2)	0.6365 (2)	0.68810 (14)	0.0164 (4)
C7	0.5265 (3)	0.7218 (2)	0.59348 (13)	0.0168 (4)
C8	0.7305 (2)	0.8271 (2)	0.59131 (13)	0.0188 (4)
H8	0.7566	0.8836	0.5275	0.023*
C9	0.8947 (2)	0.8453 (2)	0.68750 (14)	0.0187 (4)
C10	0.8595 (3)	0.7612 (2)	0.78232 (14)	0.0196 (4)
H10	0.9725	0.7736	0.8453	0.024*
C11	0.6539 (2)	0.6579 (2)	0.78256 (14)	0.0177 (4)
H11	0.6293	0.6016	0.8466	0.021*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0227 (2)	0.0314 (3)	0.0143 (2)	0.00420 (18)	0.00140 (17)	0.00786 (18)
Cl2	0.0192 (2)	0.0275 (2)	0.0273 (3)	−0.00120 (17)	0.00716 (17)	0.00581 (18)
O1	0.0182 (6)	0.0425 (8)	0.0166 (7)	0.0021 (5)	0.0021 (5)	0.0121 (6)
O2	0.0123 (5)	0.0267 (6)	0.0165 (6)	0.0012 (5)	0.0038 (4)	0.0082 (5)
N1	0.0117 (6)	0.0267 (8)	0.0213 (8)	0.0005 (6)	0.0039 (5)	0.0072 (6)
C1	0.0179 (8)	0.0266 (9)	0.0221 (10)	0.0051 (7)	0.0073 (7)	0.0061 (7)
C2	0.0191 (8)	0.0226 (9)	0.0198 (9)	0.0004 (7)	0.0059 (7)	0.0054 (7)
C3	0.0151 (8)	0.0264 (9)	0.0160 (9)	0.0002 (7)	0.0027 (7)	0.0059 (7)
C4	0.0187 (8)	0.0201 (8)	0.0162 (9)	0.0045 (7)	0.0070 (7)	0.0059 (7)
C5	0.0178 (8)	0.0218 (9)	0.0145 (9)	0.0048 (7)	0.0041 (7)	0.0056 (7)
C6	0.0184 (8)	0.0158 (8)	0.0162 (9)	0.0042 (6)	0.0061 (7)	0.0031 (6)
C7	0.0185 (8)	0.0193 (8)	0.0134 (9)	0.0070 (6)	0.0019 (6)	0.0024 (6)
C8	0.0244 (9)	0.0189 (9)	0.0165 (10)	0.0057 (7)	0.0100 (7)	0.0071 (7)
C9	0.0181 (8)	0.0170 (8)	0.0223 (9)	0.0038 (7)	0.0082 (7)	0.0024 (7)
C10	0.0189 (8)	0.0226 (9)	0.0183 (9)	0.0077 (7)	0.0022 (7)	0.0040 (7)
C11	0.0194 (8)	0.0206 (9)	0.0166 (9)	0.0079 (7)	0.0065 (7)	0.0073 (7)

Cl1—C7	1.7477 (16)	C3—C4	1.470 (2)
Cl2—C9	1.7394 (16)	C3—H3	0.9800
O1—C4	1.1976 (18)	C5—C6	1.467 (2)
O2—C4	1.3800 (19)	C5—H5	0.9300
O2—N1	1.4253 (16)	C6—C7	1.394 (2)
N1—C5	1.269 (2)	C6—C11	1.401 (2)
C1—C2	1.478 (2)	C7—C8	1.385 (2)
C1—C3	1.517 (2)	C8—C9	1.389 (2)
C1—H1A	0.9700	C8—H8	0.9300
C1—H1B	0.9700	C9—C10	1.378 (2)
C2—C3	1.508 (2)	C10—C11	1.383 (2)
C2—H2A	0.9700	C10—H10	0.9300
C2—H2B	0.9700	C11—H11	0.9300

C4—O2—N1	112.18 (11)	O2—C4—C3	109.31 (12)
C5—N1—O2	109.05 (12)	N1—C5—C6	118.94 (14)
C2—C1—C3	60.45 (11)	N1—C5—H5	120.5
C2—C1—H1A	117.7	C6—C5—H5	120.5
C3—C1—H1A	117.7	C7—C6—C11	117.60 (14)
C2—C1—H1B	117.7	C7—C6—C5	121.71 (14)
C3—C1—H1B	117.7	C11—C6—C5	120.69 (15)
H1A—C1—H1B	114.8	C8—C7—C6	122.37 (14)
C1—C2—C3	61.08 (11)	C8—C7—Cl1	116.74 (13)
C1—C2—H2A	117.7	C6—C7—Cl1	120.89 (12)
C3—C2—H2A	117.7	C7—C8—C9	117.79 (15)
C1—C2—H2B	117.7	C7—C8—H8	121.1
C3—C2—H2B	117.7	C9—C8—H8	121.1
H2A—C2—H2B	114.8	C10—C9—C8	121.89 (15)
C4—C3—C2	116.62 (14)	C10—C9—Cl2	119.36 (12)
C4—C3—C1	115.92 (13)	C8—C9—Cl2	118.75 (13)
C2—C3—C1	58.47 (11)	C9—C10—C11	119.14 (14)
C4—C3—H3	117.5	C9—C10—H10	120.4
C2—C3—H3	117.5	C11—C10—H10	120.4
C1—C3—H3	117.5	C10—C11—C6	121.20 (15)
O1—C4—O2	123.97 (14)	C10—C11—H11	119.4
O1—C4—C3	126.72 (15)	C6—C11—H11	119.4

C4—O2—N1—C5	−177.60 (13)	C5—C6—C7—C8	177.96 (16)
C1—C2—C3—C4	105.44 (16)	C11—C6—C7—Cl1	179.11 (13)
C2—C1—C3—C4	−106.64 (16)	C5—C6—C7—Cl1	−2.0 (2)
N1—O2—C4—O1	−3.1 (2)	C6—C7—C8—C9	0.4 (3)
N1—O2—C4—C3	176.04 (13)	Cl1—C7—C8—C9	−179.65 (12)
C2—C3—C4—O1	−25.6 (3)	C7—C8—C9—C10	0.6 (3)
C1—C3—C4—O1	40.4 (2)	C7—C8—C9—Cl2	−178.69 (13)
C2—C3—C4—O2	155.33 (15)	C8—C9—C10—C11	−1.1 (3)
C1—C3—C4—O2	−138.66 (14)	Cl2—C9—C10—C11	178.24 (13)
O2—N1—C5—C6	178.12 (13)	C9—C10—C11—C6	0.5 (3)
N1—C5—C6—C7	−176.72 (16)	C7—C6—C11—C10	0.5 (2)
N1—C5—C6—C11	2.2 (3)	C5—C6—C11—C10	−178.44 (16)
C11—C6—C7—C8	−1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1ⁱ	0.97	2.57	3.5008 (19)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1ⁱ	0.97	2.57	3.5008 (19)	161

Symmetry code: (i) .

5 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

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