(E)-(4-Bromo-benzyl-idene)amino cyclo-propane-carboxyl-ate.

In the title compound, C(11)H(10)BrNO(2), the dihedral angle between the benzene and cyclo-propane 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 = 268.11

Monoclinic,

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.

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

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

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

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

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

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

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

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	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*

	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)

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)