2-{5,5-Dimethyl-3-[2-(pyridin-2-yl)ethen­yl]cyclo­hex-2-enyl­idene}propane­dinitrile

Chen, L.

doi:10.1107/S1600536811001486

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o453

doi:10.1107/S1600536811001486

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2-{5,5-Dimethyl-3-[2-(pyridin-2-yl)ethenyl]cyclohex-2-enylidene}propanedinitrile

Liuqing Chen ^a ^*

^aThe College of Materials Science and Engineering, Taiyuan University of Technology, Taiyuan 030024, People's Republic of China
^*Correspondence e-mail: chenliuqingluck@163.com

(Received 10 January 2011; accepted 11 January 2011; online 22 January 2011)

The molecule of the title compound, C₁₈H₁₇N₃, with the exception of the –C(CH₃)₂ group, is nearly planar [maximum deviation: 0.208 (4), r.m.s. deviation 0.099 (6) Å] and the disubstituted C atom is displaced by 0.679 (2) Å from the mean plane through the remaining non-H atoms. In the crystal, the packing is stabilized by weak C—H⋯π interactions.

Related literature

For the synthesis, see: Lemke (1970 ). For a related structure, see: Kolev et al. (2001 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₁₇N₃
M_r = 275.35
Triclinic, $[P \overline 1]$
a = 8.4910 (17) Å
b = 9.6516 (19) Å
c = 9.6532 (19) Å
α = 89.06 (3)°
β = 70.47 (3)°
γ = 87.02 (3)°
V = 744.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.24 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.982, T_max = 0.993
5037 measured reflections
2617 independent reflections
2076 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 1.07
2617 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯Cg1ⁱ	0.97	2.77	3.6933 (16)	160
Symmetry code: (i) -x+2, -y, -z+2.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001486/dn2652sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001486/dn2652Isup2.hkl

checkCIF report

Comment top

Since discovery of their solvatochromic behaviour (Lemke, 1970), derivatives of 2-(5,5-dimethyl-3-styrylcyclohexenylidene)malononitrile have attracted considerable interest for numerous applications, such as candidates for non-linear optical (NLO), organic light emitting diodes(OLED). As part of our investigations on organic electrooptical materials, 2-(3-(2-vinyl pyridine)-5,5-dimethylcyclohex-2-enylidene)malononitrile (VPDEM)(I) was synthesized according to the general procedure described by Lemke (1970). An X-ray crystal structure determination of (I) was undertaken in order to elucidate the conformation, and the results are presented here.

With the exception of the C(CH₃)₂ group, the molecule of the title compound is nearly planar; the disubstituted C atom being displaced by -0.679 (2) Å from the mean plane of the remaining non-H atoms (Fig. 1). The disubstuted cyclohexene ring has an envelope conformation with puckering parameters: Q= 0.4657 (13) Å, θ= 126.97 (16)° and ϕ= 323.0 (2)° (Cremer & Pople, 1975).The the 2-vinylpyridine is planar with the largest deviation from the plane being -0.0876 (8)Å at C8. The bond distances and angles within the 5,5-dimethylcyclohex-2-enylidene) malononitrile are in agreement with the related 2-(3-(2-(4-Hydroxyphenyl)vinyl)-5,5-dimethylcyclohex-2-en-1-ylidene)-malononitrile (Kolev et al., 2001).

In the crystal, the packing is stabilized by weak C-H···π between the C9 methylene group of the cyclohexene ring and the symmetry related pyridine ring and Van der Waals forces.

Related literature top

For the synthesis, see: Lemke (1970). For a related structure, see: Kolev et al. (2001). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The compound was synthesized in a manner similar to the general procedure described by Lemke (1970). And the preparation of compound 2-(3,5,5,-trimethylcyclohex-2-enylidene)malononitrile was previously reported by Kolev (Kolev, et al. 2001). Malononitrile (1.87 g, 28.3 mmol) and isophorone (3.90 g, 28.3 mmol) were added to a solution of acetic acid (28µl), acetic anhydride (18µl), piperidine (380µl) and DMF (5.0 ml). The mixture was stirred at room temperature for 1 h and then at 80°C for 1 h. Then pyridine-2-carboxaldehyde (3.3789 g, 0.0122 mol) was added, and the reaction mixture was stirred at 80°C for 1 h. The mixture was poured into 200 ml of hot water containing 6 ml concentrated HCl and the precipitate was washed by water for three times. The solid was collected by filtration under reduced pressure and the crystals were grown from an CH₃CN solution by slow evaporation at room temperature over a period of several days with a yield of 63%; ¹H NMR(300 MHz, CDCl₃): 1.03(s, 6H), 2.57(s, 2H), 2.64(s, 2H), 6.95(s,1H), 7.28(d, 2H), 7.64(d, 2H), 7.81~7.87(m, 1H), 8.61(d, 1H); IR(KBr, cm^-1) ν:3404, 2962, 2224, 1609, 1574, 1522, 1462, 1322, 1262, 1210, 1158, 1097, 960, 890, 760; Anal. Calcd. For C₁₈ H₁₇ N₃: C 78.45; H 6.17; N 15.25; Found: C78.41; H 6.17; N 15.22.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. Molecular view of the title compound with the atom labeling for non-H atoms. Displacement ellipsoids are darwn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

2-{5,5-Dimethyl-3-[2-(pyridin-2-yl)ethenyl]cyclohex-2-enylidene}propanedinitrile top

Crystal data top

C₁₈H₁₇N₃	Z = 2
M_r = 275.35	F(000) = 292
Triclinic, P1	D_x = 1.228 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4910 (17) Å	Cell parameters from 3453 reflections
b = 9.6516 (19) Å	θ = 2.5–27.2°
c = 9.6532 (19) Å	µ = 0.07 mm⁻¹
α = 89.06 (3)°	T = 293 K
β = 70.47 (3)°	Block, colorless
γ = 87.02 (3)°	0.24 × 0.20 × 0.10 mm
V = 744.6 (3) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2617 independent reflections
Radiation source: fine-focus sealed tube	2076 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −10→10
T_min = 0.982, T_max = 0.993	k = −11→11
5037 measured reflections	l = −8→11

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0694P)²] where P = (F_o² + 2F_c²)/3
2617 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₁₇N₃	γ = 87.02 (3)°
M_r = 275.35	V = 744.6 (3) Å³
Triclinic, P1	Z = 2
a = 8.4910 (17) Å	Mo Kα radiation
b = 9.6516 (19) Å	µ = 0.07 mm⁻¹
c = 9.6532 (19) Å	T = 293 K
α = 89.06 (3)°	0.24 × 0.20 × 0.10 mm
β = 70.47 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2617 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	2076 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.993	R_int = 0.020
5037 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.07	Δρ_max = 0.23 e Å⁻³
2617 reflections	Δρ_min = −0.20 e Å⁻³
192 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N1	1.27970 (12)	−0.18230 (11)	0.77938 (12)	0.0255 (3)
N2	1.19520 (13)	0.35307 (12)	0.25775 (12)	0.0284 (3)
N3	0.71256 (14)	0.57738 (13)	0.39307 (14)	0.0374 (3)
C1	1.39339 (16)	−0.27762 (14)	0.79280 (15)	0.0301 (4)
H1	1.5036	−0.2707	0.7316	0.036*
C2	1.35746 (17)	−0.38617 (14)	0.89219 (15)	0.0291 (3)
H2	1.4413	−0.4502	0.8967	0.035*
C3	1.19582 (17)	−0.39740 (14)	0.98393 (15)	0.0289 (3)
H3	1.1678	−0.4690	1.0521	0.035*
C4	1.07473 (16)	−0.29945 (14)	0.97293 (14)	0.0245 (3)
H4	0.9644	−0.3042	1.0345	0.029*
C5	1.12001 (14)	−0.19426 (13)	0.86906 (13)	0.0196 (3)
C6	0.99405 (14)	−0.09422 (13)	0.84861 (13)	0.0197 (3)
H6	0.8844	−0.0997	0.9117	0.024*
C7	1.02591 (14)	0.00468 (13)	0.74519 (13)	0.0195 (3)
H7	1.1372	0.0131	0.6873	0.023*
C8	0.90367 (14)	0.09977 (13)	0.71496 (13)	0.0182 (3)
C9	0.72124 (14)	0.09492 (13)	0.80722 (13)	0.0196 (3)
H9A	0.7055	0.1347	0.9028	0.024*
H9B	0.6922	−0.0014	0.8223	0.024*
C10	0.60033 (14)	0.17193 (13)	0.74062 (13)	0.0194 (3)
C11	0.67159 (14)	0.31267 (13)	0.68002 (13)	0.0199 (3)
H11A	0.5989	0.3598	0.6333	0.024*
H11B	0.6737	0.3702	0.7608	0.024*
C12	0.84488 (14)	0.29522 (13)	0.57089 (13)	0.0184 (3)
C13	0.95597 (14)	0.19220 (13)	0.60334 (13)	0.0199 (3)
H13	1.0684	0.1887	0.5455	0.024*
C14	0.57912 (15)	0.08771 (14)	0.61607 (14)	0.0267 (3)
H14A	0.5279	0.0026	0.6546	0.040*
H14B	0.6867	0.0673	0.5435	0.040*
H14C	0.5094	0.1403	0.5717	0.040*
C15	0.42935 (15)	0.19588 (14)	0.85935 (14)	0.0260 (3)
H15A	0.3547	0.2455	0.8181	0.039*
H15B	0.4412	0.2491	0.9382	0.039*
H15C	0.3848	0.1081	0.8964	0.039*
C16	0.89702 (14)	0.37719 (13)	0.44842 (13)	0.0191 (3)
C17	1.06329 (15)	0.36272 (12)	0.34315 (13)	0.0207 (3)
C18	0.79250 (15)	0.48667 (14)	0.41784 (14)	0.0234 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0191 (5)	0.0285 (7)	0.0261 (6)	0.0033 (5)	−0.0046 (5)	0.0038 (5)
N2	0.0253 (6)	0.0333 (7)	0.0253 (6)	−0.0041 (5)	−0.0067 (5)	0.0063 (5)
N3	0.0384 (7)	0.0344 (8)	0.0440 (8)	−0.0003 (6)	−0.0207 (6)	0.0118 (6)
C1	0.0261 (7)	0.0339 (8)	0.0295 (8)	0.0080 (6)	−0.0096 (6)	0.0005 (7)
C2	0.0344 (8)	0.0250 (8)	0.0327 (8)	0.0088 (6)	−0.0190 (7)	−0.0039 (6)
C3	0.0424 (8)	0.0199 (7)	0.0304 (8)	−0.0028 (6)	−0.0201 (7)	0.0067 (6)
C4	0.0263 (7)	0.0245 (8)	0.0240 (7)	−0.0045 (6)	−0.0098 (6)	0.0043 (6)
C5	0.0217 (7)	0.0190 (7)	0.0191 (6)	−0.0012 (5)	−0.0082 (5)	−0.0004 (5)
C6	0.0172 (6)	0.0211 (7)	0.0189 (6)	−0.0006 (5)	−0.0035 (5)	−0.0002 (5)
C7	0.0169 (6)	0.0209 (7)	0.0187 (6)	0.0011 (5)	−0.0036 (5)	0.0000 (5)
C8	0.0188 (6)	0.0185 (7)	0.0161 (6)	−0.0012 (5)	−0.0042 (5)	−0.0021 (5)
C9	0.0189 (6)	0.0198 (7)	0.0173 (6)	−0.0001 (5)	−0.0026 (5)	0.0023 (5)
C10	0.0172 (6)	0.0215 (7)	0.0179 (6)	−0.0017 (5)	−0.0039 (5)	0.0026 (5)
C11	0.0184 (6)	0.0207 (7)	0.0208 (6)	0.0014 (5)	−0.0072 (5)	0.0015 (5)
C12	0.0195 (6)	0.0177 (7)	0.0199 (6)	−0.0035 (5)	−0.0087 (5)	−0.0003 (5)
C13	0.0159 (6)	0.0216 (7)	0.0204 (6)	0.0000 (5)	−0.0040 (5)	0.0010 (5)
C14	0.0266 (7)	0.0306 (8)	0.0239 (7)	−0.0076 (6)	−0.0089 (6)	0.0013 (6)
C15	0.0190 (7)	0.0321 (8)	0.0245 (7)	0.0016 (6)	−0.0049 (6)	0.0055 (6)
C16	0.0185 (6)	0.0196 (7)	0.0204 (7)	−0.0033 (5)	−0.0077 (5)	0.0018 (5)
C17	0.0258 (7)	0.0187 (7)	0.0213 (7)	−0.0050 (5)	−0.0124 (6)	0.0056 (5)
C18	0.0243 (7)	0.0256 (8)	0.0219 (7)	−0.0058 (6)	−0.0095 (6)	0.0053 (6)

Geometric parameters (Å, º) top

N1—C1	1.3352 (17)	C9—H9A	0.9700
N1—C5	1.3526 (16)	C9—H9B	0.9700
N2—C17	1.1476 (16)	C10—C14	1.5267 (17)
N3—C18	1.1507 (17)	C10—C15	1.5284 (17)
C1—C2	1.384 (2)	C10—C11	1.5415 (18)
C1—H1	0.9300	C11—C12	1.4990 (17)
C2—C3	1.3709 (19)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.3895 (18)	C12—C16	1.3694 (18)
C3—H3	0.9300	C12—C13	1.4374 (17)
C4—C5	1.3904 (19)	C13—H13	0.9300
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.4638 (17)	C14—H14B	0.9600
C6—C7	1.3402 (19)	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—C8	1.4490 (17)	C15—H15B	0.9600
C7—H7	0.9300	C15—H15C	0.9600
C8—C13	1.3578 (18)	C16—C18	1.4349 (18)
C8—C9	1.5095 (16)	C16—C17	1.4388 (17)
C9—C10	1.5382 (17)

C1—N1—C5	117.15 (12)	C15—C10—C9	109.57 (10)
N1—C1—C2	124.07 (13)	C14—C10—C11	109.23 (10)
N1—C1—H1	118.0	C15—C10—C11	109.62 (10)
C2—C1—H1	118.0	C9—C10—C11	108.81 (10)
C3—C2—C1	118.69 (12)	C12—C11—C10	111.68 (10)
C3—C2—H2	120.7	C12—C11—H11A	109.3
C1—C2—H2	120.7	C10—C11—H11A	109.3
C2—C3—C4	118.58 (13)	C12—C11—H11B	109.3
C2—C3—H3	120.7	C10—C11—H11B	109.3
C4—C3—H3	120.7	H11A—C11—H11B	107.9
C3—C4—C5	119.43 (12)	C16—C12—C13	121.43 (11)
C3—C4—H4	120.3	C16—C12—C11	121.50 (11)
C5—C4—H4	120.3	C13—C12—C11	117.03 (11)
N1—C5—C4	122.06 (12)	C8—C13—C12	122.75 (11)
N1—C5—C6	117.04 (12)	C8—C13—H13	118.6
C4—C5—C6	120.86 (11)	C12—C13—H13	118.6
C7—C6—C5	124.47 (11)	C10—C14—H14A	109.5
C7—C6—H6	117.8	C10—C14—H14B	109.5
C5—C6—H6	117.8	H14A—C14—H14B	109.5
C6—C7—C8	126.26 (11)	C10—C14—H14C	109.5
C6—C7—H7	116.9	H14A—C14—H14C	109.5
C8—C7—H7	116.9	H14B—C14—H14C	109.5
C13—C8—C7	119.05 (11)	C10—C15—H15A	109.5
C13—C8—C9	121.08 (11)	C10—C15—H15B	109.5
C7—C8—C9	119.87 (11)	H15A—C15—H15B	109.5
C8—C9—C10	114.54 (10)	C10—C15—H15C	109.5
C8—C9—H9A	108.6	H15A—C15—H15C	109.5
C10—C9—H9A	108.6	H15B—C15—H15C	109.5
C8—C9—H9B	108.6	C12—C16—C18	122.74 (11)
C10—C9—H9B	108.6	C12—C16—C17	122.27 (11)
H9A—C9—H9B	107.6	C18—C16—C17	114.97 (11)
C14—C10—C15	108.76 (10)	N2—C17—C16	178.78 (14)
C14—C10—C9	110.84 (10)	N3—C18—C16	177.81 (14)

C13—C8—C9—C10	15.38 (17)	C10—C11—C12—C13	−40.03 (15)
C7—C8—C9—C10	−164.63 (10)	C7—C8—C13—C12	−176.48 (10)
C8—C9—C10—C14	76.11 (13)	C9—C8—C13—C12	3.51 (19)
C8—C9—C10—C15	−163.85 (10)	C11—C12—C13—C8	9.42 (18)
C8—C9—C10—C11	−44.02 (14)	C11—C12—C16—C18	1.62 (19)
C14—C10—C11—C12	−65.09 (13)	C13—C12—C16—C17	1.87 (18)
C9—C10—C11—C12	56.03 (13)	C11—C12—C16—C17	179.46 (11)
C10—C11—C12—C16	142.28 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cg1ⁱ	0.97	2.77	3.6933 (16)	160

Symmetry code: (i) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇N₃
M_r	275.35
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.4910 (17), 9.6516 (19), 9.6532 (19)
α, β, γ (°)	89.06 (3), 70.47 (3), 87.02 (3)
V (Å³)	744.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.24 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.982, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	5037, 2617, 2076
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.07
No. of reflections	2617
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.20

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXTL/PC (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cg1ⁱ	0.97	2.77	3.6933 (16)	160

Symmetry code: (i) −x+2, −y, −z+2.

Acknowledgements

The author acknowledges financial support from the Natural Science Foundation of Shanxi Province (2010021023–2, 2008011008)

References

Bruker (2000). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kolev, T., Glavcheva, Z., Yancheva, D., Schürmann, M., Kleb, D.-C., Preut, H. & Bleckmann, P. (2001). Acta Cryst. E57, o561–o562. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o453

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-{5,5-Di­methyl-3-[2-(pyridin-2-yl)ethen­yl]cyclo­hex-2-enyl­­idene}propane­di­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-{5,5-Dimethyl-3-[2-(pyridin-2-yl)ethenyl]cyclohex-2-enylidene}propanedinitrile