(E)-1-Bromo-4-(2-nitro-prop-1-en-yl)benzene.

The title compound, C(9)H(8)BrNO(2), which was synthesized by the condensation of 4-bromo-benzaldehyde with nitro-ethane, possesses a trans configuration. The dihedral angle between the benzene ring and the mean plane of the double bond is 7.31 (3)°. The crystal structure is stabilized by short inter-molecular Br⋯O contacts [3.168 (4) Å].

Related literature

For general background to nitro­alkenes as inter­mediates in the preparation of numerous products including insecticides and pharmacologically active substances, see: Boelle et al. (1998 ▶); Vallejos et al. (2005 ▶). For related structures, see: Boys et al. (1993 ▶); Mugnoli et al. (1991 ▶).

Experimental

Crystal data

C9H8BrNO2

M = 242.07

Triclinic,

a = 6.9787 (5) Å

b = 7.4123 (5) Å

c = 9.7659 (6) Å

α = 105.435 (2)°

β = 95.087 (2)°

γ = 104.323 (2)°

V = 465.31 (5) Å3

Z = 2

Mo Kα radiation

μ = 4.38 mm−1

T = 296 K

0.21 × 0.19 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.388, T max = 0.703

4605 measured reflections

2112 independent reflections

1303 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.00

2112 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.71 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048910/zq2017sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048910/zq2017Isup2.hkl

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

C9H8BrNO2	Z = 2
Mr = 242.07	F(000) = 240
Triclinic, P1	Dx = 1.728 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9787 (5) Å	Cell parameters from 3184 reflections
b = 7.4123 (5) Å	θ = 3.1–27.4°
c = 9.7659 (6) Å	µ = 4.38 mm−1
α = 105.435 (2)°	T = 296 K
β = 95.087 (2)°	Platelet, yellow
γ = 104.323 (2)°	0.21 × 0.19 × 0.08 mm
V = 465.31 (5) Å3

Rigaku R-AXIS RAPID diffractometer	2112 independent reflections
Radiation source: rolling anode	1303 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→8
Tmin = 0.388, Tmax = 0.703	l = −12→12
4605 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.012P)2 + 0.950P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2112 reflections	Δρmax = 0.46 e Å−3
120 parameters	Δρmin = −0.71 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0149 (13)

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	0.90197 (7)	0.24927 (9)	0.09032 (5)	0.0754 (2)
N1	0.2076 (6)	0.2311 (6)	0.7592 (4)	0.0660 (10)
O1	0.2341 (5)	0.2609 (6)	0.8891 (4)	0.0937 (12)
O2	0.0411 (5)	0.1719 (7)	0.6875 (4)	0.1038 (14)
C8	0.3870 (6)	0.2659 (6)	0.6875 (4)	0.0514 (9)
C1	0.7334 (6)	0.2408 (6)	0.2327 (4)	0.0567 (10)
C5	0.4097 (6)	0.1824 (7)	0.2989 (4)	0.0631 (12)
H5	0.2712	0.1456	0.2720	0.076*
C7	0.3513 (6)	0.2154 (7)	0.5461 (4)	0.0594 (11)
H7	0.2165	0.1633	0.5051	0.071*
C4	0.4907 (6)	0.2283 (6)	0.4430 (4)	0.0524 (10)
C3	0.6976 (6)	0.2770 (8)	0.4767 (5)	0.0776 (15)
H3	0.7569	0.3055	0.5720	0.093*
C9	0.5777 (7)	0.3501 (9)	0.7900 (5)	0.0825 (16)
H9A	0.6349	0.2476	0.7987	0.099*
H9B	0.5528	0.4165	0.8825	0.099*
H9C	0.6694	0.4409	0.7555	0.099*
C2	0.8179 (6)	0.2840 (8)	0.3723 (5)	0.0742 (14)
H2	0.9565	0.3183	0.3976	0.089*
C6	0.5299 (6)	0.1901 (7)	0.1943 (4)	0.0680 (13)
H6	0.4727	0.1609	0.0985	0.082*

	U11	U22	U33	U12	U13	U23
Br1	0.0560 (3)	0.1058 (5)	0.0598 (3)	0.0136 (2)	0.0153 (2)	0.0237 (3)
N1	0.055 (2)	0.081 (3)	0.055 (2)	0.0147 (19)	0.0103 (18)	0.014 (2)
O1	0.076 (2)	0.142 (4)	0.056 (2)	0.019 (2)	0.0205 (17)	0.025 (2)
O2	0.0467 (19)	0.173 (4)	0.074 (2)	0.017 (2)	0.0114 (17)	0.020 (2)
C8	0.045 (2)	0.056 (3)	0.050 (2)	0.0112 (18)	0.0092 (17)	0.0142 (19)
C1	0.052 (2)	0.066 (3)	0.052 (2)	0.013 (2)	0.0100 (19)	0.019 (2)
C5	0.042 (2)	0.087 (3)	0.050 (2)	0.012 (2)	−0.0015 (18)	0.012 (2)
C7	0.043 (2)	0.077 (3)	0.051 (2)	0.015 (2)	0.0032 (17)	0.012 (2)
C4	0.042 (2)	0.064 (3)	0.048 (2)	0.0140 (19)	0.0039 (16)	0.013 (2)
C3	0.050 (2)	0.134 (5)	0.044 (2)	0.024 (3)	−0.0013 (19)	0.022 (3)
C9	0.052 (3)	0.122 (5)	0.055 (3)	0.008 (3)	0.003 (2)	0.015 (3)
C2	0.038 (2)	0.123 (4)	0.055 (3)	0.018 (2)	0.0015 (19)	0.022 (3)
C6	0.047 (2)	0.103 (4)	0.045 (2)	0.013 (2)	0.0013 (18)	0.017 (2)

Br1—C1	1.902 (4)	C7—C4	1.466 (5)
N1—O2	1.214 (5)	C7—H7	0.9300
N1—O1	1.217 (4)	C4—C3	1.385 (6)
N1—C8	1.488 (5)	C3—C2	1.380 (6)
C8—C7	1.314 (5)	C3—H3	0.9300
C8—C9	1.478 (6)	C9—H9A	0.9600
C1—C2	1.357 (6)	C9—H9B	0.9600
C1—C6	1.366 (6)	C9—H9C	0.9600
C5—C6	1.381 (6)	C2—H2	0.9300
C5—C4	1.388 (5)	C6—H6	0.9300
C5—H5	0.9300
O2—N1—O1	122.1 (4)	C5—C4—C7	117.7 (4)
O2—N1—C8	119.7 (4)	C2—C3—C4	121.6 (4)
O1—N1—C8	118.2 (4)	C2—C3—H3	119.2
C7—C8—C9	130.9 (4)	C4—C3—H3	119.2
C7—C8—N1	115.8 (4)	C8—C9—H9A	109.5
C9—C8—N1	113.2 (3)	C8—C9—H9B	109.5
C2—C1—C6	120.5 (4)	H9A—C9—H9B	109.5
C2—C1—Br1	119.2 (3)	C8—C9—H9C	109.5
C6—C1—Br1	120.3 (3)	H9A—C9—H9C	109.5
C6—C5—C4	121.6 (4)	H9B—C9—H9C	109.5
C6—C5—H5	119.2	C1—C2—C3	119.9 (4)
C4—C5—H5	119.2	C1—C2—H2	120.0
C8—C7—C4	130.1 (4)	C3—C2—H2	120.0
C8—C7—H7	115.0	C1—C6—C5	119.5 (4)
C4—C7—H7	115.0	C1—C6—H6	120.2
C3—C4—C5	116.9 (4)	C5—C6—H6	120.2
C3—C4—C7	125.4 (4)
O2—N1—C8—C7	−4.8 (6)	C8—C7—C4—C5	−173.5 (5)
O1—N1—C8—C7	174.2 (5)	C5—C4—C3—C2	1.5 (8)
O2—N1—C8—C9	176.1 (5)	C7—C4—C3—C2	179.4 (5)
O1—N1—C8—C9	−4.9 (6)	C6—C1—C2—C3	−0.1 (8)
C9—C8—C7—C4	−0.7 (9)	Br1—C1—C2—C3	−179.5 (4)
N1—C8—C7—C4	−179.7 (4)	C4—C3—C2—C1	−0.6 (8)
C6—C5—C4—C3	−1.8 (7)	C2—C1—C6—C5	−0.2 (8)
C6—C5—C4—C7	−179.8 (4)	Br1—C1—C6—C5	179.2 (4)
C8—C7—C4—C3	8.7 (8)	C4—C5—C6—C1	1.1 (8)