(E)-2-[1-(4-Fluoro-phen-yl)pent-1-en-3-yl-idene]malononitrile.

The title mol-ecule, C(14)H(11)FN(2), is approximately planar except the ethyl group, the maximum atomic deviation being 0.105 (5) Å. The fluoro-phenyl ring and 2-propyl-idene-malononitrile unit are located on the opposite sides of the C=C double bond, showing an E configuration.

Related literature

The title compound is a diene reagent in Diels–Alder reactions. For the use of malononitrile-containing compounds as building blocks in organic synthesis, see: Liu et al. (2002 ▶); Sepiol & Milart (1985 ▶); Zhang et al. (2003 ▶). For related structures, see: Kang & Chen (2009 ▶).

Experimental

Crystal data

C14H11FN2

M = 226.25

Monoclinic,

a = 7.6504 (2) Å

b = 12.4989 (3) Å

c = 12.7787 (3) Å

β = 98.375 (2)°

V = 1208.89 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.70 mm−1

T = 291 K

0.42 × 0.38 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.758, T max = 0.808

5033 measured reflections

2148 independent reflections

1956 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.117

S = 1.06

2148 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035884/xu5286sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035884/xu5286Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035884/xu5286Isup3.cml

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

C14H11FN2	F(000) = 472
Mr = 226.25	Dx = 1.243 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 3458 reflections
a = 7.6504 (2) Å	θ = 3.5–71.8°
b = 12.4989 (3) Å	µ = 0.70 mm−1
c = 12.7787 (3) Å	T = 291 K
β = 98.375 (2)°	Block, yellow
V = 1208.89 (5) Å3	0.42 × 0.38 × 0.32 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	2148 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1956 reflections with I > 2σ(I)
mirror	Rint = 0.014
Detector resolution: 15.9149 pixels mm-1	θmax = 67.1°, θmin = 5.0°
ω scans	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→11
Tmin = 0.758, Tmax = 0.808	l = −15→13
5033 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0672P)2 + 0.0976P] where P = (Fo2 + 2Fc2)/3
2148 reflections	(Δ/σ)max = 0.005
155 parameters	Δρmax = 0.10 e Å−3
0 restraints	Δρmin = −0.14 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
C11	0.29662 (18)	−0.17966 (10)	0.91075 (11)	0.0583 (3)
F1	0.17654 (14)	0.52071 (7)	0.95680 (10)	0.0992 (4)
C9	0.49407 (15)	−0.06063 (10)	0.82906 (9)	0.0500 (3)
C4	0.36822 (15)	0.23270 (9)	0.86946 (9)	0.0483 (3)
N1	0.18077 (18)	−0.19553 (12)	0.95555 (12)	0.0819 (4)
C5	0.45722 (17)	0.32820 (10)	0.85718 (11)	0.0595 (3)
H5	0.5624	0.3264	0.8288	0.071*
C13	0.65462 (17)	−0.04859 (10)	0.77465 (10)	0.0571 (3)
H13A	0.6384	0.0122	0.7270	0.069*
H13B	0.6677	−0.1120	0.7327	0.069*
C3	0.21017 (16)	0.23790 (10)	0.91178 (9)	0.0515 (3)
H3	0.1477	0.1754	0.9201	0.062*
C14	0.82131 (18)	−0.03252 (13)	0.85331 (12)	0.0704 (4)
H14A	0.8075	0.0290	0.8964	0.106*
H14B	0.9199	−0.0217	0.8158	0.106*
H14C	0.8420	−0.0947	0.8975	0.106*
C12	0.53656 (19)	−0.25427 (10)	0.83029 (11)	0.0611 (4)
C7	0.44770 (16)	0.13350 (9)	0.83921 (10)	0.0520 (3)
H7	0.5433	0.1410	0.8024	0.062*
C10	0.44336 (16)	−0.16038 (9)	0.85528 (10)	0.0523 (3)
C2	0.14552 (18)	0.33429 (10)	0.94140 (11)	0.0593 (3)
H2	0.0406	0.3374	0.9700	0.071*
C1	0.23896 (19)	0.42570 (10)	0.92788 (12)	0.0633 (4)
C8	0.40019 (15)	0.03307 (9)	0.85783 (9)	0.0509 (3)
H8	0.3012	0.0228	0.8912	0.061*
C6	0.39336 (19)	0.42521 (10)	0.88608 (12)	0.0658 (4)
H6	0.4536	0.4885	0.8774	0.079*
N2	0.6121 (2)	−0.32851 (10)	0.81089 (12)	0.0867 (5)

	U11	U22	U33	U12	U13	U23
C11	0.0574 (7)	0.0436 (6)	0.0741 (8)	−0.0017 (5)	0.0100 (6)	0.0036 (5)
F1	0.1059 (7)	0.0510 (5)	0.1490 (10)	0.0130 (5)	0.0465 (7)	−0.0189 (5)
C9	0.0499 (6)	0.0461 (6)	0.0545 (6)	0.0027 (5)	0.0096 (5)	−0.0024 (5)
C4	0.0484 (6)	0.0419 (6)	0.0560 (6)	0.0011 (5)	0.0119 (5)	0.0056 (5)
N1	0.0709 (8)	0.0697 (8)	0.1101 (10)	−0.0068 (6)	0.0300 (7)	0.0134 (7)
C5	0.0540 (7)	0.0479 (7)	0.0808 (9)	−0.0026 (5)	0.0244 (6)	0.0060 (6)
C13	0.0607 (7)	0.0498 (7)	0.0650 (7)	0.0045 (5)	0.0232 (6)	−0.0012 (5)
C3	0.0504 (6)	0.0452 (6)	0.0602 (7)	−0.0003 (5)	0.0131 (5)	0.0067 (5)
C14	0.0541 (7)	0.0799 (10)	0.0803 (9)	0.0043 (6)	0.0203 (6)	0.0063 (7)
C12	0.0687 (8)	0.0465 (7)	0.0672 (8)	0.0053 (6)	0.0064 (6)	−0.0044 (6)
C7	0.0501 (6)	0.0472 (7)	0.0617 (7)	0.0028 (5)	0.0179 (5)	0.0031 (5)
C10	0.0539 (7)	0.0426 (6)	0.0606 (7)	0.0020 (5)	0.0091 (5)	−0.0019 (5)
C2	0.0557 (7)	0.0562 (8)	0.0694 (8)	0.0066 (5)	0.0203 (6)	0.0020 (6)
C1	0.0691 (8)	0.0453 (7)	0.0774 (8)	0.0094 (6)	0.0166 (6)	−0.0048 (6)
C8	0.0503 (6)	0.0436 (6)	0.0615 (7)	0.0018 (5)	0.0170 (5)	0.0013 (5)
C6	0.0701 (8)	0.0417 (7)	0.0878 (9)	−0.0069 (6)	0.0190 (7)	0.0015 (6)
N2	0.1048 (11)	0.0568 (8)	0.0969 (10)	0.0233 (7)	0.0096 (8)	−0.0131 (6)

C11—N1	1.1404 (18)	C3—C2	1.3762 (17)
C11—C10	1.4326 (19)	C3—H3	0.9300
F1—C1	1.3514 (15)	C14—H14A	0.9600
C9—C10	1.3620 (17)	C14—H14B	0.9600
C9—C8	1.4489 (16)	C14—H14C	0.9600
C9—C13	1.5045 (17)	C12—N2	1.1393 (18)
C4—C5	1.3943 (16)	C12—C10	1.4331 (17)
C4—C3	1.3961 (16)	C7—C8	1.3378 (16)
C4—C7	1.4577 (16)	C7—H7	0.9300
C5—C6	1.3777 (18)	C2—C1	1.372 (2)
C5—H5	0.9300	C2—H2	0.9300
C13—C14	1.518 (2)	C1—C6	1.365 (2)
C13—H13A	0.9700	C8—H8	0.9300
C13—H13B	0.9700	C6—H6	0.9300
N1—C11—C10	179.39 (16)	C13—C14—H14C	109.5
C10—C9—C8	120.53 (11)	H14A—C14—H14C	109.5
C10—C9—C13	119.09 (11)	H14B—C14—H14C	109.5
C8—C9—C13	120.31 (10)	N2—C12—C10	179.37 (16)
C5—C4—C3	117.93 (11)	C8—C7—C4	128.05 (11)
C5—C4—C7	117.97 (11)	C8—C7—H7	116.0
C3—C4—C7	124.09 (10)	C4—C7—H7	116.0
C6—C5—C4	121.68 (12)	C9—C10—C11	123.19 (11)
C6—C5—H5	119.2	C9—C10—C12	121.73 (12)
C4—C5—H5	119.2	C11—C10—C12	115.07 (11)
C9—C13—C14	111.77 (11)	C1—C2—C3	118.66 (12)
C9—C13—H13A	109.3	C1—C2—H2	120.7
C14—C13—H13A	109.3	C3—C2—H2	120.7
C9—C13—H13B	109.3	F1—C1—C6	118.11 (12)
C14—C13—H13B	109.3	F1—C1—C2	119.08 (12)
H13A—C13—H13B	107.9	C6—C1—C2	122.81 (11)
C2—C3—C4	120.90 (11)	C7—C8—C9	123.76 (11)
C2—C3—H3	119.5	C7—C8—H8	118.1
C4—C3—H3	119.5	C9—C8—H8	118.1
C13—C14—H14A	109.5	C1—C6—C5	118.00 (12)
C13—C14—H14B	109.5	C1—C6—H6	121.0
H14A—C14—H14B	109.5	C5—C6—H6	121.0
C3—C4—C5—C6	0.4 (2)	C13—C9—C10—C12	−1.42 (19)
C7—C4—C5—C6	−178.49 (13)	C4—C3—C2—C1	0.4 (2)
C10—C9—C13—C14	−91.40 (14)	C3—C2—C1—F1	−179.96 (13)
C8—C9—C13—C14	85.53 (14)	C3—C2—C1—C6	0.1 (2)
C5—C4—C3—C2	−0.66 (19)	C4—C7—C8—C9	−176.65 (12)
C7—C4—C3—C2	178.11 (12)	C10—C9—C8—C7	176.67 (12)
C5—C4—C7—C8	169.58 (13)	C13—C9—C8—C7	−0.22 (19)
C3—C4—C7—C8	−9.2 (2)	F1—C1—C6—C5	179.66 (14)
C8—C9—C10—C11	0.61 (19)	C2—C1—C6—C5	−0.4 (2)
C13—C9—C10—C11	177.53 (12)	C4—C5—C6—C1	0.2 (2)
C8—C9—C10—C12	−178.34 (11)