(E)-(4-Bromo­benzyl­idene)amino cyclo­propane­carboxyl­ate

Liu, X.-H.; Tan, C.-X.; Weng, J.-Q.; Liu, H.-J.

doi:10.1107/S1600536812002048

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o493

doi:10.1107/S1600536812002048

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(E)-(4-Bromobenzylidene)amino cyclopropanecarboxylate

Xing-Hai Liu,^a,^b Cheng-Xia Tan,^b Jian-Quan Weng ^b and Hui-Jun Liu ^b ^*

^aKey Laboratory of Pesticide Chemistry and Applications, Ministry of Agriculture, Beijing, People's Republic of China, and ^bCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: xhliu@zjut.edu.cn

(Received 8 November 2011; accepted 17 January 2012; online 21 January 2012)

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).

Experimental

Crystal data

C₁₁H₁₀BrNO₂
M_r = 268.11
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.082
S = 0.96
1862 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002048/ds2156sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812002048/ds2156Isup3.cml

checkCIF report

Related literature top

For details of the synthesis, see: Liu et al. (2011a). For the KARI activities [define KARI] of related compounds, see: Liu et al. (2009a,b, 2010, 2011b,d). For a related structure, see: Liu et al. (2011c).

Experimental top

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.

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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. 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. The crystal packing for (I).

(E)-(4-Bromobenzylidene)amino cyclopropanecarboxylate top

Crystal data top

C₁₁H₁₀BrNO₂	F(000) = 536
M_r = 268.11	D_x = 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

Data collection top

Rigaku Saturn diffractometer	1862 independent reflections
Radiation source: rotating anode	1320 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.096
ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −15→14
T_min = 0.577, T_max = 0.654	k = −15→16
5989 measured reflections	l = −6→5

Refinement top

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(F_o²) + (0.0236P)²] where P = (F_o² + 2F_c²)/3
1862 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

C₁₁H₁₀BrNO₂	V = 1058.3 (4) Å³
M_r = 268.11	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.209 (3) Å	µ = 3.86 mm⁻¹
b = 13.789 (3) Å	T = 113 K
c = 5.8714 (12) Å	0.16 × 0.14 × 0.12 mm
β = 98.27 (3)°

Data collection top

Rigaku Saturn diffractometer	1862 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1320 reflections with I > 2σ(I)
T_min = 0.577, T_max = 0.654	R_int = 0.096
5989 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 0.96	Δρ_max = 0.67 e Å⁻³
1862 reflections	Δρ_min = −0.74 e Å⁻³
136 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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀BrNO₂
M_r	268.11
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	13.209 (3), 13.789 (3), 5.8714 (12)
β (°)	98.27 (3)
V (Å³)	1058.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.86
Crystal size (mm)	0.16 × 0.14 × 0.12

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.577, 0.654
No. of measured, independent and observed [I > 2σ(I)] reflections	5989, 1862, 1320
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.082, 0.96
No. of reflections	1862
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.74

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

Acknowledgements

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

References

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