2-[(E)-4-(2-Bromo-phen-yl)but-3-en-2-yl-idene]malononitrile.

The title compound, C(13)H(19)BrN(2), is planar structure except for the methyl H atoms, the maximum atomic deviation for the non-H atoms being 0.100 (1) Å. The bromo-phenyl and isopropanylidenemalononitrile units are located on opposite sides of the C=C bond, showing an E configuration.

Related literature

For the use of malononitrile-containing compounds as building blocks in syntheses, see: Liu et al. (2002 ▶); Sepiol & Milart (1985 ▶); Zhang et al. (2003 ▶). For a related structure, see: Chen & Kang (2010 ▶).

Experimental

Crystal data

C13H9BrN2

M = 273.13

Triclinic,

a = 7.0353 (7) Å

b = 7.0765 (5) Å

c = 13.3229 (8) Å

α = 82.192 (6)°

β = 76.628 (8)°

γ = 66.038 (9)°

V = 589.03 (8) Å3

Z = 2

Cu Kα radiation

μ = 4.52 mm−1

T = 291 K

0.36 × 0.32 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.293, T max = 0.410

4500 measured reflections

2062 independent reflections

1923 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.06

2062 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.55 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049536/xu5097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049536/xu5097Isup2.hkl

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

C13H9BrN2	Z = 2
Mr = 273.13	F(000) = 272
Triclinic, P1	Dx = 1.540 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.0353 (7) Å	Cell parameters from 3664 reflections
b = 7.0765 (5) Å	θ = 6.8–71.9°
c = 13.3229 (8) Å	µ = 4.52 mm−1
α = 82.192 (6)°	T = 291 K
β = 76.628 (8)°	Block, yellow
γ = 66.038 (9)°	0.36 × 0.32 × 0.24 mm
V = 589.03 (8) Å3

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	2062 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1923 reflections with I > 2σ(I)
mirror	Rint = 0.024
Detector resolution: 7.9575 pixels mm-1	θmax = 67.0°, θmin = 6.8°
ω scans	h = −8→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −8→8
Tmin = 0.293, Tmax = 0.410	l = −15→15
4500 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0759P)2 + 0.0933P] where P = (Fo2 + 2Fc2)/3
2062 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.55 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	0.67339 (5)	0.15902 (4)	0.54256 (2)	0.06643 (19)
C8	0.8775 (4)	−0.3609 (4)	0.7789 (2)	0.0493 (6)
H8	0.8557	−0.3515	0.8499	0.059*
N2	1.2571 (5)	−1.0939 (4)	0.7188 (2)	0.0735 (8)
C11	1.0519 (4)	−0.7373 (4)	0.7984 (2)	0.0455 (5)
C4	0.5298 (5)	0.2647 (5)	0.8955 (2)	0.0598 (7)
H4	0.4994	0.2887	0.9655	0.072*
C13	1.0087 (4)	−0.7342 (4)	0.9092 (2)	0.0527 (6)
C5	0.6402 (5)	0.0655 (4)	0.8620 (2)	0.0563 (6)
H5	0.6835	−0.0433	0.9103	0.068*
C9	0.9905 (4)	−0.5636 (4)	0.7362 (2)	0.0461 (5)
C7	0.8037 (4)	−0.1879 (4)	0.7217 (2)	0.0516 (6)
H7	0.8277	−0.2024	0.6510	0.062*
C2	0.5107 (4)	0.3937 (4)	0.7208 (3)	0.0563 (7)
H2	0.4684	0.5041	0.6732	0.068*
C10	1.0389 (5)	−0.5797 (5)	0.6211 (2)	0.0584 (7)
H10A	1.1160	−0.7222	0.6044	0.088*
H10B	1.1228	−0.5013	0.5895	0.088*
H10C	0.9087	−0.5260	0.5958	0.088*
C6	0.6889 (4)	0.0226 (4)	0.7573 (2)	0.0478 (6)
N1	0.9737 (5)	−0.7329 (5)	0.9974 (2)	0.0749 (8)
C3	0.4644 (4)	0.4289 (4)	0.8242 (3)	0.0604 (7)
H3	0.3891	0.5629	0.8466	0.072*
C12	1.1667 (4)	−0.9376 (4)	0.7555 (2)	0.0532 (6)
C1	0.6206 (4)	0.1936 (4)	0.6873 (2)	0.0496 (6)

	U11	U22	U33	U12	U13	U23
Br1	0.0880 (3)	0.0444 (2)	0.0549 (3)	−0.01383 (17)	−0.01666 (17)	0.00310 (15)
C8	0.0616 (14)	0.0331 (13)	0.0509 (14)	−0.0141 (11)	−0.0134 (11)	−0.0042 (10)
N2	0.0868 (17)	0.0364 (14)	0.0813 (19)	−0.0086 (12)	−0.0094 (14)	−0.0120 (13)
C11	0.0542 (12)	0.0334 (12)	0.0467 (13)	−0.0140 (10)	−0.0109 (10)	−0.0024 (10)
C4	0.0712 (16)	0.0478 (15)	0.0555 (16)	−0.0208 (13)	−0.0032 (13)	−0.0105 (12)
C13	0.0673 (15)	0.0354 (13)	0.0519 (17)	−0.0138 (11)	−0.0196 (12)	0.0028 (11)
C5	0.0706 (16)	0.0384 (14)	0.0559 (16)	−0.0179 (12)	−0.0128 (12)	0.0009 (12)
C9	0.0549 (12)	0.0336 (12)	0.0481 (14)	−0.0145 (10)	−0.0117 (10)	−0.0024 (10)
C7	0.0654 (14)	0.0336 (13)	0.0522 (15)	−0.0145 (11)	−0.0141 (11)	−0.0015 (11)
C2	0.0583 (14)	0.0329 (13)	0.0699 (19)	−0.0105 (11)	−0.0140 (13)	0.0022 (12)
C10	0.0780 (17)	0.0425 (15)	0.0469 (15)	−0.0169 (13)	−0.0093 (13)	−0.0031 (11)
C6	0.0539 (13)	0.0318 (12)	0.0551 (15)	−0.0140 (10)	−0.0119 (11)	0.0003 (10)
N1	0.105 (2)	0.0617 (17)	0.0521 (17)	−0.0232 (15)	−0.0236 (14)	0.0012 (12)
C3	0.0602 (15)	0.0371 (14)	0.076 (2)	−0.0120 (11)	−0.0060 (13)	−0.0109 (13)
C12	0.0629 (15)	0.0354 (14)	0.0566 (16)	−0.0150 (12)	−0.0122 (12)	0.0011 (12)
C1	0.0508 (12)	0.0359 (13)	0.0575 (15)	−0.0125 (10)	−0.0116 (11)	0.0009 (11)

Br1—C1	1.908 (3)	C5—H5	0.9300
C8—C7	1.327 (4)	C9—C10	1.502 (4)
C8—C9	1.449 (4)	C7—C6	1.461 (4)
C8—H8	0.9300	C7—H7	0.9300
N2—C12	1.140 (4)	C2—C3	1.373 (5)
C11—C9	1.358 (4)	C2—C1	1.387 (4)
C11—C12	1.437 (4)	C2—H2	0.9300
C11—C13	1.438 (4)	C10—H10A	0.9600
C4—C5	1.383 (4)	C10—H10B	0.9600
C4—C3	1.390 (5)	C10—H10C	0.9600
C4—H4	0.9300	C6—C1	1.412 (4)
C13—N1	1.144 (4)	C3—H3	0.9300
C5—C6	1.401 (4)
C7—C8—C9	123.3 (3)	C3—C2—C1	120.0 (3)
C7—C8—H8	118.4	C3—C2—H2	120.0
C9—C8—H8	118.4	C1—C2—H2	120.0
C9—C11—C12	120.8 (2)	C9—C10—H10A	109.5
C9—C11—C13	123.1 (2)	C9—C10—H10B	109.5
C12—C11—C13	116.1 (2)	H10A—C10—H10B	109.5
C5—C4—C3	119.7 (3)	C9—C10—H10C	109.5
C5—C4—H4	120.2	H10A—C10—H10C	109.5
C3—C4—H4	120.2	H10B—C10—H10C	109.5
N1—C13—C11	179.5 (3)	C5—C6—C1	116.6 (2)
C4—C5—C6	121.9 (3)	C5—C6—C7	122.1 (2)
C4—C5—H5	119.0	C1—C6—C7	121.3 (3)
C6—C5—H5	119.0	C2—C3—C4	120.2 (3)
C11—C9—C8	121.1 (2)	C2—C3—H3	119.9
C11—C9—C10	120.0 (2)	C4—C3—H3	119.9
C8—C9—C10	119.0 (2)	N2—C12—C11	178.1 (3)
C8—C7—C6	127.4 (3)	C2—C1—C6	121.5 (3)
C8—C7—H7	116.3	C2—C1—Br1	117.1 (2)
C6—C7—H7	116.3	C6—C1—Br1	121.4 (2)
C9—C11—C13—N1	131 (44)	C8—C7—C6—C5	−0.8 (5)
C12—C11—C13—N1	−49 (45)	C8—C7—C6—C1	179.5 (3)
C3—C4—C5—C6	−0.1 (5)	C1—C2—C3—C4	0.9 (4)
C12—C11—C9—C8	−179.0 (2)	C5—C4—C3—C2	−0.5 (5)
C13—C11—C9—C8	0.7 (4)	C9—C11—C12—N2	−6(10)
C12—C11—C9—C10	1.1 (4)	C13—C11—C12—N2	175 (10)
C13—C11—C9—C10	−179.1 (3)	C3—C2—C1—C6	−0.6 (4)
C7—C8—C9—C11	−176.0 (3)	C3—C2—C1—Br1	178.9 (2)
C7—C8—C9—C10	3.8 (4)	C5—C6—C1—C2	0.0 (4)
C9—C8—C7—C6	−179.9 (3)	C7—C6—C1—C2	179.7 (3)
C4—C5—C6—C1	0.4 (4)	C5—C6—C1—Br1	−179.5 (2)
C4—C5—C6—C7	−179.4 (3)	C7—C6—C1—Br1	0.2 (3)