2-{5,5-Di­methyl-3-[2-(2-methoxy­phenyl)­vinyl]­cyclo­hex-2-enyl­idene}malono­nitrile

The title mol­ecule, C₂₀H₂₀N₂O, is nearly planar except for the C(CH₃)₂ group. The disubstituted C atom is displaced by 0.635 (2) Å from the mean plane of the remaining atoms of the cyclo­hexene ring.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.125
• Data-to-parameter ratio = 18.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSMU_01  Alert C The ratio of given/expected absorption coefficient lies
          outside the range 0.99 <> 1.01
          Calculated value of mu =     0.073
          Value of mu given      =     0.070

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(7)   -   C(8)   =       1.43 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(7)   -   C(9)   =       1.43 Ang.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).

(I)

Crystal data

C20H20N2O	Dx = 1.180 Mg m^−3
Mr = 304.38	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 20401 reflections
a = 13.1374 (3) Å	θ = 3.1–27.5°
b = 13.2089 (3) Å	µ = 0.07 mm^−1
c = 19.7506 (4) Å	T = 291 K
V = 3427.33 (13) Å^3	Plate, yellow
Z = 8	0.5 × 0.4 × 0.1 mm
F(000) = 1296

Data collection

Nonius KappaCCD diffractometer	1907 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
Detector resolution: 10 vertical, 18 horizontal pixels mm^-1	h = −17→17
198 frames via ω–rotation (Δω=1°) with 2 sets at different κ–angles and two times 10 s per frame scans	k = −17→17
20402 measured reflections	l = −25→25
3890 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.059P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
3890 reflections	Δρmax = 0.14 e Å^−3
212 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0077 (9)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.46315 (10)	0.23212 (9)	0.72462 (6)	0.0657 (4)
N1	0.93705 (13)	−0.27298 (13)	0.42465 (9)	0.0826 (6)
N2	0.61234 (14)	−0.32673 (13)	0.43363 (8)	0.0771 (5)
C1	0.64207 (12)	−0.02054 (12)	0.57643 (7)	0.0449 (4)
C2	0.65555 (12)	−0.09737 (12)	0.53187 (7)	0.0484 (4)
H2A	0.5982	−0.1309	0.5158	0.058*
C3	0.75271 (12)	−0.12940 (11)	0.50843 (7)	0.0435 (4)
C4	0.84300 (12)	−0.06699 (13)	0.52766 (7)	0.0486 (4)
H4A	0.8510	−0.0124	0.4953	0.058*
H4B	0.9037	−0.1087	0.5257	0.058*
C5	0.83251 (12)	−0.02203 (12)	0.59921 (8)	0.0493 (4)
C6	0.73255 (11)	0.03647 (13)	0.60289 (8)	0.0538 (5)
H6A	0.7198	0.0548	0.6497	0.065*
H6B	0.7397	0.0987	0.5772	0.065*
C7	0.76302 (13)	−0.21379 (12)	0.46917 (7)	0.0466 (4)
C8	0.85982 (15)	−0.24642 (13)	0.44472 (9)	0.0565 (5)
C9	0.67828 (15)	−0.27521 (13)	0.44927 (8)	0.0541 (5)
C10	0.83346 (15)	−0.10775 (14)	0.65131 (8)	0.0728 (6)
H10A	0.8266	−0.0799	0.6960	0.109*
H10B	0.8965	−0.1441	0.6481	0.109*
H10C	0.7778	−0.1530	0.6425	0.109*
C11	0.92227 (13)	0.04892 (15)	0.61252 (9)	0.0742 (6)
H11A	0.9167	0.0766	0.6573	0.111*
H11B	0.9216	0.1029	0.5800	0.111*
H11C	0.9848	0.0118	0.6086	0.111*
C12	0.54031 (12)	0.00338 (12)	0.59807 (7)	0.0492 (4)
H12A	0.4884	−0.0333	0.5775	0.059*
C13	0.51110 (12)	0.07165 (12)	0.64404 (7)	0.0488 (4)
H13A	0.5615	0.1116	0.6635	0.059*
C14	0.40676 (12)	0.08869 (13)	0.66618 (7)	0.0468 (4)
C15	0.32710 (13)	0.02411 (14)	0.64868 (8)	0.0573 (5)
H15A	0.3414	−0.0335	0.6233	0.069*
C16	0.22798 (14)	0.04275 (16)	0.66763 (9)	0.0666 (5)
H16A	0.1764	−0.0018	0.6552	0.080*
C17	0.20584 (15)	0.12745 (18)	0.70494 (9)	0.0699 (6)
H17A	0.1388	0.1411	0.7170	0.084*
C18	0.28212 (15)	0.19223 (16)	0.72462 (8)	0.0654 (5)
H18A	0.2666	0.2493	0.7502	0.079*
C19	0.38256 (14)	0.17281 (14)	0.70640 (8)	0.0519 (5)
C20	0.44540 (17)	0.31847 (15)	0.76664 (9)	0.0814 (6)
H20A	0.5091	0.3505	0.7770	0.122*
H20B	0.4129	0.2974	0.8078	0.122*
H20C	0.4022	0.3655	0.7432	0.122*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0619 (9)	0.0677 (9)	0.0676 (8)	0.0103 (7)	0.0068 (6)	−0.0208 (6)
N1	0.0646 (12)	0.0794 (12)	0.1037 (13)	0.0184 (10)	0.0111 (10)	−0.0235 (10)
N2	0.0811 (13)	0.0677 (11)	0.0823 (11)	−0.0139 (10)	−0.0013 (10)	−0.0082 (9)
C1	0.0404 (10)	0.0466 (10)	0.0476 (9)	0.0030 (8)	0.0057 (8)	0.0000 (8)
C2	0.0395 (10)	0.0527 (10)	0.0530 (9)	−0.0021 (8)	0.0038 (8)	−0.0061 (8)
C3	0.0448 (10)	0.0442 (9)	0.0416 (8)	0.0027 (8)	0.0055 (8)	0.0030 (7)
C4	0.0414 (10)	0.0524 (10)	0.0519 (9)	0.0006 (8)	0.0087 (8)	−0.0015 (8)
C5	0.0362 (10)	0.0600 (11)	0.0516 (10)	−0.0018 (8)	0.0041 (8)	−0.0062 (8)
C6	0.0443 (11)	0.0592 (11)	0.0578 (10)	−0.0025 (9)	0.0049 (8)	−0.0121 (8)
C7	0.0464 (11)	0.0441 (10)	0.0492 (9)	0.0044 (8)	0.0053 (8)	0.0001 (8)
C8	0.0575 (13)	0.0481 (11)	0.0638 (11)	0.0062 (9)	0.0015 (10)	−0.0098 (8)
C9	0.0608 (13)	0.0470 (10)	0.0546 (10)	0.0020 (10)	0.0060 (9)	−0.0039 (8)
C10	0.0618 (13)	0.0975 (15)	0.0591 (11)	0.0087 (11)	0.0003 (9)	0.0113 (11)
C11	0.0466 (12)	0.0922 (15)	0.0837 (12)	−0.0099 (10)	0.0044 (10)	−0.0296 (11)
C12	0.0401 (10)	0.0548 (10)	0.0527 (9)	0.0010 (8)	0.0022 (8)	−0.0065 (8)
C13	0.0427 (10)	0.0541 (11)	0.0497 (9)	0.0051 (8)	−0.0002 (8)	−0.0033 (8)
C14	0.0431 (10)	0.0549 (10)	0.0426 (9)	0.0096 (9)	0.0032 (8)	0.0024 (8)
C15	0.0482 (11)	0.0671 (12)	0.0565 (10)	0.0040 (10)	0.0063 (9)	0.0000 (9)
C16	0.0477 (12)	0.0911 (15)	0.0609 (11)	−0.0004 (10)	0.0069 (9)	0.0080 (11)
C17	0.0460 (13)	0.1059 (17)	0.0577 (11)	0.0175 (12)	0.0121 (10)	0.0129 (11)
C18	0.0618 (14)	0.0829 (14)	0.0516 (10)	0.0247 (12)	0.0111 (10)	−0.0017 (9)
C19	0.0493 (12)	0.0625 (12)	0.0438 (9)	0.0103 (10)	0.0027 (8)	0.0010 (8)
C20	0.0974 (17)	0.0705 (14)	0.0763 (12)	0.0148 (12)	0.0088 (12)	−0.0220 (10)

Geometric parameters (Å, º)

O1—C19	1.365 (2)	C10—H10B	0.9600
O1—C20	1.4296 (19)	C10—H10C	0.9600
N1—C8	1.144 (2)	C11—H11A	0.9600
N2—C9	1.144 (2)	C11—H11B	0.9600
C1—C2	1.355 (2)	C11—H11C	0.9600
C1—C12	1.439 (2)	C12—C13	1.336 (2)
C1—C6	1.501 (2)	C12—H12A	0.9300
C2—C3	1.422 (2)	C13—C14	1.456 (2)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C7	1.365 (2)	C14—C15	1.394 (2)
C3—C4	1.494 (2)	C14—C19	1.402 (2)
C4—C5	1.539 (2)	C15—C16	1.377 (2)
C4—H4A	0.9700	C15—H15A	0.9300
C4—H4B	0.9700	C16—C17	1.371 (3)
C5—C6	1.526 (2)	C16—H16A	0.9300
C5—C11	1.529 (2)	C17—C18	1.374 (3)
C5—C10	1.530 (2)	C17—H17A	0.9300
C6—H6A	0.9700	C18—C19	1.392 (2)
C6—H6B	0.9700	C18—H18A	0.9300
C7—C8	1.427 (2)	C20—H20A	0.9600
C7—C9	1.432 (3)	C20—H20B	0.9600
C10—H10A	0.9600	C20—H20C	0.9600
C19—O1—C20	118.96 (14)	H10B—C10—H10C	109.5
C2—C1—C12	118.62 (14)	C5—C11—H11A	109.5
C2—C1—C6	119.89 (14)	C5—C11—H11B	109.5
C12—C1—C6	121.48 (14)	H11A—C11—H11B	109.5
C1—C2—C3	123.48 (15)	C5—C11—H11C	109.5
C1—C2—H2A	118.3	H11A—C11—H11C	109.5
C3—C2—H2A	118.3	H11B—C11—H11C	109.5
C7—C3—C2	121.14 (15)	C13—C12—C1	128.10 (15)
C7—C3—C4	121.10 (14)	C13—C12—H12A	115.9
C2—C3—C4	117.76 (14)	C1—C12—H12A	115.9
C3—C4—C5	112.05 (12)	C12—C13—C14	125.37 (16)
C3—C4—H4A	109.2	C12—C13—H13A	117.3
C5—C4—H4A	109.2	C14—C13—H13A	117.3
C3—C4—H4B	109.2	C15—C14—C19	117.08 (15)
C5—C4—H4B	109.2	C15—C14—C13	122.52 (15)
H4A—C4—H4B	107.9	C19—C14—C13	120.39 (16)
C6—C5—C11	110.20 (14)	C16—C15—C14	122.22 (17)
C6—C5—C10	110.47 (13)	C16—C15—H15A	118.9
C11—C5—C10	109.37 (14)	C14—C15—H15A	118.9
C6—C5—C4	108.44 (13)	C17—C16—C15	119.51 (18)
C11—C5—C4	108.99 (13)	C17—C16—H16A	120.2
C10—C5—C4	109.35 (13)	C15—C16—H16A	120.2
C1—C6—C5	114.27 (13)	C16—C17—C18	120.37 (17)
C1—C6—H6A	108.7	C16—C17—H17A	119.8
C5—C6—H6A	108.7	C18—C17—H17A	119.8
C1—C6—H6B	108.7	C17—C18—C19	120.25 (18)
C5—C6—H6B	108.7	C17—C18—H18A	119.9
H6A—C6—H6B	107.6	C19—C18—H18A	119.9
C3—C7—C8	121.84 (15)	O1—C19—C18	124.16 (17)
C3—C7—C9	122.78 (15)	O1—C19—C14	115.35 (15)
C8—C7—C9	115.38 (14)	C18—C19—C14	120.49 (18)
N1—C8—C7	179.4 (2)	O1—C20—H20A	109.5
N2—C9—C7	178.0 (2)	O1—C20—H20B	109.5
C5—C10—H10A	109.5	H20A—C20—H20B	109.5
C5—C10—H10B	109.5	O1—C20—H20C	109.5
H10A—C10—H10B	109.5	H20A—C20—H20C	109.5
C5—C10—H10C	109.5	H20B—C20—H20C	109.5
H10A—C10—H10C	109.5
C12—C1—C2—C3	−178.24 (14)	C2—C1—C12—C13	175.90 (15)
C6—C1—C2—C3	0.8 (2)	C6—C1—C12—C13	−3.2 (3)
C1—C2—C3—C7	173.03 (14)	C1—C12—C13—C14	−176.71 (15)
C1—C2—C3—C4	−7.6 (2)	C12—C13—C14—C15	9.9 (2)
C7—C3—C4—C5	−145.22 (14)	C12—C13—C14—C19	−169.69 (15)
C2—C3—C4—C5	35.36 (19)	C19—C14—C15—C16	2.2 (2)
C3—C4—C5—C6	−54.49 (18)	C13—C14—C15—C16	−177.47 (14)
C3—C4—C5—C11	−174.47 (14)	C14—C15—C16—C17	0.1 (3)
C3—C4—C5—C10	66.02 (17)	C15—C16—C17—C18	−1.4 (3)
C2—C1—C6—C5	−23.0 (2)	C16—C17—C18—C19	0.5 (3)
C12—C1—C6—C5	156.10 (13)	C20—O1—C19—C18	1.8 (2)
C11—C5—C6—C1	167.78 (13)	C20—O1—C19—C14	−178.91 (14)
C10—C5—C6—C1	−71.25 (17)	C17—C18—C19—O1	−178.94 (15)
C4—C5—C6—C1	48.56 (18)	C17—C18—C19—C14	1.8 (3)
C2—C3—C7—C8	179.41 (15)	C15—C14—C19—O1	177.62 (13)
C4—C3—C7—C8	0.0 (2)	C13—C14—C19—O1	−2.7 (2)
C2—C3—C7—C9	−0.2 (2)	C15—C14—C19—C18	−3.1 (2)
C4—C3—C7—C9	−179.57 (14)	C13—C14—C19—C18	176.56 (14)