2-[5,5-Di­methyl-3-(2-p-tolyl-vinyl)-cyclo­hex-2-enyl­idene]-malono­nitrile

Kolev, T.; Yancheva, D.; Schürmann, M.; Kleb, D.-C.; Preut, H.; Spiteller, M.

doi:10.1107/S1600536802015891

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2-[5,5-Dimethyl-3-(2-p-tolyl-vinyl)-cyclohex-2-enylidene]-malononitrile

T. Kolev, D. Yancheva, M. Schürmann, D.-C. Kleb, H. Preut and M. Spiteller

The crystal structure of the title compound, C₂₀H₂₀N₂, contains two independent molecules in the asymmetric unit. These molecules differ significantly only in the torsion angles of the dimethylcyclohexene moieties, which have twisted conformations. The molecules are nearly planar except for the C(CH₃)₂ groups.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802015891/cv6143sup1.cif Contains datablocks I, ccd1755
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802015891/cv6143Isup2.hkl Contains datablock I

CCDC reference: 198954

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.082
Data-to-parameter ratio = 19.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(7)   -   C(7')  =       1.42 Ang.

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(27)  -   C(27') =       1.43 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(27') -   C(28)  =       1.44 Ang.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 4 Alert Level C = Please check

Comment top

In the course of our investigations on organic electro-optical, non-linear optical and photorefractive materials we determined the crystal structure of the title compound, (I). As a result of its solvatochromism, it is expected to be a good candidate for photorefractive and electro-optical applications.

The conversion of basic 2-(3,5,5-trimethyl-cyclohex-2-enylidene)-malononitrile into the corresponding 2-[5,5-dimethyl-3-(2-p-tolyl-vinyl)-cyclohex-2-enylidene]-malononitrile is a way to enhance the charge-transfer transition on the molecular level – a requisite for the design of efficient second- and third-order non-linear optical materials.

The crystal contains no classical H-bonds, but C11—H11···N21 [H···A = 2.62, D···A = 3.391 (2) Å, D—H···A = 141°] is a possible non-classical H-bond.

The dihedral angle between the least-squares planes through atoms C1, C2, C3, C11, C12 and through C13, C14, C15, C16, C17, C18 is 8.24 (9)°, whereas the corresponding angle in the other molecule in the asymmetric unit is only 3.74 (9)°

Experimental top

The title compound was synthesized for the first time, according to a general procedure described by Lemke (1970): 3.72 g (20 mmol) 2-(3,5,5-trimethyl-cyclohex-2-enylidene)-malononitrile and 3.71 ml (20 mmol) 4-methyl-benzaldehyde were dissolved in 80 ml dry toluene by continuous stirring and heating under reflux for 60 min. Piperidine (1 ml) was used as a catalyst. After a few minutes, the solution became dark red. The bright-yellow precipitate was obtained after evaporation of the solvent. The product was filtered and washed with ethanol and recrystallized from ethyl acetate. Yield of the recrystallized product: 33%; melting point: 428–429 K. UV-vis(EtOH): λ_max (log ε) = 270.5 nm (3.702), 398.5 nm (4.329).

The purity of the compound was confirmed by elemental analysis, IR, UV–vis and mass spectrometry. Crystals were grown from ethyl acetate by slow evaporation at room temperature over a period of a week.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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), PLATON (Spek, 2001).

Figures top

Fig. 1. : View of the title compound, showing the labelling of all non-H atoms. Displacement ellipsoids are shown at 50% probability levels. H atoms are omitted for clarity.

(I) top

Crystal data top

C₂₀H₂₀N₂	F(000) = 1232
M_r = 288.38	D_x = 1.095 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.5270 (3) Å	Cell parameters from 62924 reflections
b = 16.1781 (3) Å	θ = 3.0–27.5°
c = 16.3616 (4) Å	µ = 0.06 mm⁻¹
β = 102.3807 (9)°	T = 291 K
V = 3497.32 (13) Å³	Block, orange
Z = 8	0.50 × 0.40 × 0.32 mm

Data collection top

Nonius KappaCCD diffractometer	2602 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −17→17
332 frames via ω–rotation (Δω=1%) and two times 50 s per frame (7 sets at different κ–angles) scans	k = −20→20
62924 measured reflections	l = −21→20
7998 independent reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.020P)²] where P = (F_o² + 2F_c²)/3
7998 reflections	(Δ/σ)_max = 0.004
403 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₀H₂₀N₂	V = 3497.32 (13) Å³
M_r = 288.38	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.5270 (3) Å	µ = 0.06 mm⁻¹
b = 16.1781 (3) Å	T = 291 K
c = 16.3616 (4) Å	0.50 × 0.40 × 0.32 mm
β = 102.3807 (9)°

Data collection top

Nonius KappaCCD diffractometer	2602 reflections with I > 2σ(I)
62924 measured reflections	R_int = 0.021
7998 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.11 e Å⁻³
7998 reflections	Δρ_min = −0.16 e Å⁻³
403 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N11	1.37461 (12)	1.07691 (10)	0.20345 (10)	0.1155 (6)
N12	1.04516 (14)	1.04989 (11)	0.12227 (13)	0.1379 (7)
C1	1.19046 (11)	1.22876 (11)	0.17206 (9)	0.0604 (4)
C2	1.09392 (11)	1.26751 (10)	0.15643 (9)	0.0680 (5)
H2	1.0367	1.2342	0.1437	0.082*
C3	1.08103 (11)	1.34968 (11)	0.15904 (9)	0.0623 (4)
C4	1.17014 (11)	1.40573 (9)	0.17793 (9)	0.0728 (5)
H4A	1.1829	1.4205	0.2367	0.087*
H4B	1.1539	1.4561	0.1457	0.087*
C5	1.26668 (11)	1.36884 (10)	0.15884 (10)	0.0642 (4)
C6	1.28160 (10)	1.28266 (9)	0.19747 (9)	0.0667 (4)
H6A	1.3387	1.2564	0.1808	0.080*
H6B	1.2978	1.2878	0.2579	0.080*
C7'	1.19918 (13)	1.14513 (12)	0.16686 (10)	0.0703 (5)
C7	1.29627 (16)	1.10696 (10)	0.18646 (11)	0.0831 (6)
C8	1.11342 (17)	1.09183 (13)	0.14237 (13)	0.0931 (6)
C9	1.25917 (11)	1.36340 (10)	0.06422 (10)	0.0894 (5)
H9A	1.2023	1.3296	0.0394	0.134*
H9B	1.3200	1.3393	0.0536	0.134*
H9C	1.2505	1.4178	0.0404	0.134*
C10	1.35787 (11)	1.42245 (10)	0.19752 (10)	0.1041 (6)
H10A	1.4179	1.3995	0.1842	0.156*
H10B	1.3652	1.4240	0.2572	0.156*
H10C	1.3478	1.4775	0.1755	0.156*
C11	0.97749 (12)	1.38139 (10)	0.14388 (9)	0.0728 (5)
H11	0.9258	1.3431	0.1272	0.087*
C12	0.94999 (12)	1.45826 (11)	0.15134 (9)	0.0735 (5)
H12	1.0018	1.4968	0.1664	0.088*
C13	0.84572 (11)	1.49007 (11)	0.13833 (9)	0.0618 (4)
C14	0.76117 (13)	1.44029 (10)	0.10865 (9)	0.0742 (5)
H14	0.7698	1.3852	0.0955	0.089*
C15	0.66467 (12)	1.47273 (12)	0.09870 (9)	0.0777 (5)
H15	0.6091	1.4387	0.0794	0.093*
C16	0.64903 (12)	1.55413 (13)	0.11672 (10)	0.0707 (5)
C17	0.73269 (14)	1.60248 (10)	0.14484 (9)	0.0733 (5)
H17	0.7240	1.6579	0.1568	0.088*
C18	0.82856 (12)	1.57138 (11)	0.15581 (9)	0.0693 (5)
H18	0.8834	1.6059	0.1755	0.083*
C19	0.54425 (11)	1.59006 (11)	0.10691 (11)	0.1130 (7)
H19A	0.5363	1.6125	0.1595	0.170*
H19B	0.4948	1.5475	0.0894	0.170*
H19C	0.5349	1.6331	0.0656	0.170*
N21	0.85430 (12)	1.20647 (10)	0.17807 (12)	0.1281 (7)
N22	0.53030 (14)	1.23723 (10)	0.09187 (12)	0.1345 (7)
C21	0.66978 (11)	1.05270 (11)	0.13122 (9)	0.0607 (4)
C22	0.57310 (11)	1.01495 (10)	0.11321 (9)	0.0648 (4)
H22	0.5167	1.0486	0.0958	0.078*
C23	0.55808 (11)	0.93317 (10)	0.11985 (9)	0.0593 (4)
C24	0.64602 (10)	0.87616 (9)	0.14470 (9)	0.0664 (4)
H24A	0.6301	0.8242	0.1151	0.080*
H24B	0.6558	0.8648	0.2041	0.080*
C25	0.74496 (11)	0.90951 (9)	0.12691 (10)	0.0612 (4)
C26	0.76026 (10)	0.99808 (9)	0.15887 (9)	0.0660 (4)
H26A	0.7776	0.9971	0.2195	0.079*
H26B	0.8171	1.0219	0.1397	0.079*
C27'	0.68112 (13)	1.13673 (12)	0.12954 (10)	0.0708 (5)
C27	0.77752 (16)	1.17541 (11)	0.15513 (12)	0.0871 (6)
C28	0.59609 (16)	1.19229 (12)	0.10832 (12)	0.0893 (6)
C29	0.83399 (10)	0.85649 (9)	0.17207 (10)	0.0927 (6)
H29A	0.8255	0.8008	0.1514	0.139*
H29B	0.8361	0.8567	0.2311	0.139*
H29C	0.8961	0.8787	0.1620	0.139*
C30	0.74160 (11)	0.90711 (9)	0.03272 (10)	0.0907 (5)
H30A	0.7330	0.8511	0.0132	0.136*
H30B	0.8037	0.9288	0.0222	0.136*
H30C	0.6859	0.9400	0.0038	0.136*
C31	0.45442 (11)	0.90331 (10)	0.10517 (9)	0.0688 (5)
H31	0.4038	0.9428	0.0904	0.083*
C32	0.42446 (12)	0.82642 (10)	0.11044 (9)	0.0736 (5)
H32	0.4752	0.7870	0.1250	0.088*
C33	0.32006 (12)	0.79614 (12)	0.09597 (9)	0.0666 (5)
C34	0.23642 (13)	0.84819 (11)	0.07418 (9)	0.0804 (5)
H34	0.2459	0.9044	0.0667	0.097*
C35	0.13982 (13)	0.81694 (14)	0.06364 (10)	0.0876 (6)
H35	0.0851	0.8527	0.0487	0.105*
C36	0.12179 (14)	0.73462 (15)	0.07453 (10)	0.0792 (6)
C37	0.20395 (16)	0.68380 (11)	0.09348 (11)	0.0892 (6)
H37	0.1940	0.6274	0.0992	0.107*
C38	0.30084 (13)	0.71359 (12)	0.10440 (10)	0.0825 (5)
H38	0.3549	0.6770	0.1178	0.099*
C39	0.01594 (11)	0.70198 (12)	0.06891 (10)	0.1205 (7)
H39A	0.0017	0.6999	0.1239	0.181*
H39B	0.0107	0.6474	0.0453	0.181*
H39C	−0.0318	0.7378	0.0340	0.181*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.1170 (13)	0.1041 (13)	0.1325 (15)	0.0537 (11)	0.0425 (12)	0.0315 (11)
N12	0.1369 (17)	0.0865 (15)	0.182 (2)	−0.0126 (12)	0.0168 (14)	0.0068 (13)
C1	0.0638 (11)	0.0640 (13)	0.0563 (11)	0.0118 (10)	0.0191 (9)	0.0075 (9)
C2	0.0613 (11)	0.0594 (13)	0.0867 (13)	0.0066 (9)	0.0234 (9)	0.0078 (10)
C3	0.0559 (11)	0.0627 (12)	0.0723 (12)	0.0089 (10)	0.0230 (9)	0.0075 (10)
C4	0.0705 (11)	0.0646 (12)	0.0852 (12)	0.0082 (10)	0.0208 (10)	0.0023 (9)
C5	0.0559 (11)	0.0664 (12)	0.0712 (13)	−0.0013 (9)	0.0156 (9)	0.0070 (10)
C6	0.0624 (11)	0.0746 (13)	0.0634 (11)	0.0120 (10)	0.0144 (9)	0.0047 (10)
C7'	0.0800 (13)	0.0602 (13)	0.0744 (12)	0.0200 (12)	0.0248 (10)	0.0065 (10)
C7	0.1055 (15)	0.0654 (14)	0.0840 (14)	0.0240 (12)	0.0328 (13)	0.0132 (10)
C8	0.1029 (17)	0.0639 (16)	0.1135 (17)	0.0066 (12)	0.0253 (14)	0.0101 (13)
C9	0.0793 (12)	0.1126 (15)	0.0819 (14)	0.0044 (10)	0.0302 (10)	0.0250 (11)
C10	0.0774 (12)	0.0970 (15)	0.1324 (17)	−0.0158 (11)	0.0106 (11)	0.0005 (12)
C11	0.0743 (13)	0.0586 (13)	0.0887 (13)	0.0076 (10)	0.0245 (10)	0.0088 (10)
C12	0.0726 (12)	0.0708 (14)	0.0802 (13)	0.0003 (11)	0.0230 (9)	0.0051 (11)
C13	0.0462 (11)	0.0758 (14)	0.0639 (12)	0.0095 (10)	0.0128 (9)	0.0092 (10)
C14	0.0737 (12)	0.0701 (12)	0.0752 (12)	0.0131 (11)	0.0082 (10)	−0.0059 (10)
C15	0.0598 (12)	0.0867 (15)	0.0822 (13)	0.0033 (11)	0.0054 (10)	−0.0014 (11)
C16	0.0606 (12)	0.0791 (14)	0.0723 (12)	0.0123 (11)	0.0142 (10)	0.0107 (11)
C17	0.0770 (12)	0.0649 (13)	0.0836 (13)	0.0176 (11)	0.0298 (10)	0.0131 (10)
C18	0.0730 (13)	0.0615 (13)	0.0785 (12)	0.0023 (10)	0.0274 (10)	0.0060 (10)
C19	0.0696 (12)	0.1343 (18)	0.1311 (17)	0.0363 (12)	0.0124 (11)	0.0072 (13)
N21	0.1130 (14)	0.0941 (14)	0.1878 (19)	−0.0431 (11)	0.0557 (13)	−0.0135 (12)
N22	0.1422 (17)	0.0913 (14)	0.1758 (18)	0.0354 (11)	0.0467 (14)	0.0109 (12)
C21	0.0639 (11)	0.0596 (13)	0.0624 (11)	−0.0020 (10)	0.0224 (9)	−0.0031 (9)
C22	0.0559 (11)	0.0632 (12)	0.0764 (12)	−0.0004 (10)	0.0167 (9)	−0.0017 (10)
C23	0.0531 (10)	0.0604 (12)	0.0667 (11)	−0.0024 (10)	0.0180 (8)	−0.0030 (9)
C24	0.0619 (11)	0.0590 (11)	0.0796 (12)	−0.0029 (9)	0.0178 (9)	0.0000 (9)
C25	0.0572 (11)	0.0578 (12)	0.0702 (12)	0.0030 (9)	0.0174 (9)	−0.0058 (9)
C26	0.0590 (11)	0.0672 (12)	0.0741 (11)	−0.0073 (9)	0.0194 (9)	−0.0073 (10)
C27'	0.0764 (13)	0.0584 (13)	0.0839 (13)	−0.0067 (11)	0.0314 (10)	0.0011 (11)
C27	0.0995 (15)	0.0586 (13)	0.1149 (17)	−0.0135 (12)	0.0490 (14)	0.0021 (11)
C28	0.1078 (17)	0.0629 (15)	0.1046 (16)	0.0004 (12)	0.0395 (14)	−0.0024 (12)
C29	0.0715 (11)	0.0831 (13)	0.1232 (16)	0.0144 (10)	0.0205 (10)	0.0006 (11)
C30	0.0983 (13)	0.0908 (14)	0.0921 (15)	−0.0007 (10)	0.0408 (11)	−0.0169 (11)
C31	0.0647 (12)	0.0634 (12)	0.0801 (12)	0.0008 (9)	0.0197 (9)	0.0003 (10)
C32	0.0709 (12)	0.0699 (13)	0.0832 (13)	0.0007 (10)	0.0235 (10)	−0.0023 (10)
C33	0.0506 (11)	0.0791 (14)	0.0732 (12)	−0.0094 (11)	0.0202 (9)	−0.0061 (10)
C34	0.0669 (12)	0.0886 (14)	0.0857 (13)	−0.0114 (12)	0.0163 (10)	0.0147 (10)
C35	0.0628 (13)	0.1206 (19)	0.0773 (13)	−0.0042 (12)	0.0107 (10)	0.0159 (12)
C36	0.0642 (13)	0.1130 (18)	0.0617 (12)	−0.0252 (14)	0.0165 (10)	−0.0129 (12)
C37	0.0890 (14)	0.0825 (15)	0.1050 (16)	−0.0297 (14)	0.0408 (12)	−0.0234 (12)
C38	0.0717 (13)	0.0720 (15)	0.1112 (15)	−0.0085 (10)	0.0363 (11)	−0.0139 (11)
C39	0.0783 (13)	0.181 (2)	0.1025 (15)	−0.0537 (13)	0.0208 (11)	−0.0208 (13)

Geometric parameters (Å, º) top

N11—C7	1.1446 (18)	N21—C27	1.1424 (19)
N12—C8	1.136 (2)	N22—C28	1.136 (2)
C1—C7'	1.3623 (18)	C21—C27'	1.3690 (18)
C1—C2	1.4215 (18)	C21—C22	1.4160 (18)
C1—C6	1.4945 (17)	C21—C26	1.4987 (17)
C2—C3	1.3426 (17)	C22—C23	1.3465 (17)
C2—H2	0.9300	C22—H22	0.9300
C3—C11	1.4619 (18)	C23—C31	1.4535 (18)
C3—C4	1.4870 (17)	C23—C24	1.4911 (17)
C4—C5	1.5277 (17)	C24—C25	1.5279 (17)
C4—H4A	0.9700	C24—H24A	0.9700
C4—H4B	0.9700	C24—H24B	0.9700
C5—C6	1.5262 (17)	C25—C26	1.5242 (17)
C5—C10	1.5297 (17)	C25—C30	1.5324 (18)
C5—C9	1.5320 (18)	C25—C29	1.5332 (17)
C6—H6A	0.9700	C26—H26A	0.9700
C6—H6B	0.9700	C26—H26B	0.9700
C7'—C7	1.424 (2)	C27'—C27	1.426 (2)
C7'—C8	1.432 (2)	C27'—C28	1.442 (2)
C9—H9A	0.9600	C29—H29A	0.9600
C9—H9B	0.9600	C29—H29B	0.9600
C9—H9C	0.9600	C29—H29C	0.9600
C10—H10A	0.9600	C30—H30A	0.9600
C10—H10B	0.9600	C30—H30B	0.9600
C10—H10C	0.9600	C30—H30C	0.9600
C11—C12	1.3114 (17)	C31—C32	1.3168 (17)
C11—H11	0.9300	C31—H31	0.9300
C12—C13	1.4734 (19)	C32—C33	1.4653 (19)
C12—H12	0.9300	C32—H32	0.9300
C13—C18	1.3764 (18)	C33—C38	1.3731 (19)
C13—C14	1.3979 (18)	C33—C34	1.3940 (19)
C14—C15	1.3838 (18)	C34—C35	1.3770 (19)
C14—H14	0.9300	C34—H34	0.9300
C15—C16	1.3757 (19)	C35—C36	1.372 (2)
C15—H15	0.9300	C35—H35	0.9300
C16—C17	1.3716 (18)	C36—C37	1.364 (2)
C16—C19	1.5083 (19)	C36—C39	1.5104 (19)
C17—C18	1.3665 (18)	C37—C38	1.3717 (19)
C17—H17	0.9300	C37—H37	0.9300
C18—H18	0.9300	C38—H38	0.9300
C19—H19A	0.9600	C39—H39A	0.9600
C19—H19B	0.9600	C39—H39B	0.9600
C19—H19C	0.9600	C39—H39C	0.9600

C7'—C1—C2	121.01 (16)	C27'—C21—C22	121.78 (15)
C7'—C1—C6	121.31 (15)	C27'—C21—C26	120.25 (15)
C2—C1—C6	117.64 (15)	C22—C21—C26	117.81 (15)
C3—C2—C1	123.47 (15)	C23—C22—C21	123.76 (15)
C3—C2—H2	118.3	C23—C22—H22	118.1
C1—C2—H2	118.3	C21—C22—H22	118.1
C2—C3—C11	117.92 (15)	C22—C23—C31	118.04 (15)
C2—C3—C4	120.36 (14)	C22—C23—C24	120.29 (14)
C11—C3—C4	121.71 (15)	C31—C23—C24	121.63 (14)
C3—C4—C5	114.18 (13)	C23—C24—C25	114.19 (13)
C3—C4—H4A	108.7	C23—C24—H24A	108.7
C5—C4—H4A	108.7	C25—C24—H24A	108.7
C3—C4—H4B	108.7	C23—C24—H24B	108.7
C5—C4—H4B	108.7	C25—C24—H24B	108.7
H4A—C4—H4B	107.6	H24A—C24—H24B	107.6
C6—C5—C4	108.37 (12)	C26—C25—C24	109.07 (12)
C6—C5—C10	108.86 (13)	C26—C25—C30	109.97 (12)
C4—C5—C10	110.05 (14)	C24—C25—C30	110.14 (12)
C6—C5—C9	109.90 (13)	C26—C25—C29	109.01 (12)
C4—C5—C9	110.77 (12)	C24—C25—C29	109.89 (13)
C10—C5—C9	108.88 (13)	C30—C25—C29	108.75 (13)
C1—C6—C5	112.94 (12)	C21—C26—C25	114.13 (12)
C1—C6—H6A	109.0	C21—C26—H26A	108.7
C5—C6—H6A	109.0	C25—C26—H26A	108.7
C1—C6—H6B	109.0	C21—C26—H26B	108.7
C5—C6—H6B	109.0	C25—C26—H26B	108.7
H6A—C6—H6B	107.8	H26A—C26—H26B	107.6
C1—C7'—C7	120.30 (17)	C21—C27'—C27	121.95 (17)
C1—C7'—C8	122.67 (17)	C21—C27'—C28	122.46 (16)
C7—C7'—C8	117.03 (17)	C27—C27'—C28	115.41 (16)
N11—C7—C7'	178.9 (2)	N21—C27—C27'	177.9 (2)
N12—C8—C7'	179.4 (3)	N22—C28—C27'	178.8 (2)
C5—C9—H9A	109.5	C25—C29—H29A	109.5
C5—C9—H9B	109.5	C25—C29—H29B	109.5
H9A—C9—H9B	109.5	H29A—C29—H29B	109.5
C5—C9—H9C	109.5	C25—C29—H29C	109.5
H9A—C9—H9C	109.5	H29A—C29—H29C	109.5
H9B—C9—H9C	109.5	H29B—C29—H29C	109.5
C5—C10—H10A	109.5	C25—C30—H30A	109.5
C5—C10—H10B	109.5	C25—C30—H30B	109.5
H10A—C10—H10B	109.5	H30A—C30—H30B	109.5
C5—C10—H10C	109.5	C25—C30—H30C	109.5
H10A—C10—H10C	109.5	H30A—C30—H30C	109.5
H10B—C10—H10C	109.5	H30B—C30—H30C	109.5
C12—C11—C3	126.70 (16)	C32—C31—C23	127.06 (16)
C12—C11—H11	116.7	C32—C31—H31	116.5
C3—C11—H11	116.7	C23—C31—H31	116.5
C11—C12—C13	126.84 (16)	C31—C32—C33	127.21 (16)
C11—C12—H12	116.6	C31—C32—H32	116.4
C13—C12—H12	116.6	C33—C32—H32	116.4
C18—C13—C14	117.45 (14)	C38—C33—C34	116.90 (15)
C18—C13—C12	120.17 (16)	C38—C33—C32	120.37 (17)
C14—C13—C12	122.39 (17)	C34—C33—C32	122.73 (17)
C15—C14—C13	120.22 (16)	C35—C34—C33	120.44 (17)
C15—C14—H14	119.9	C35—C34—H34	119.8
C13—C14—H14	119.9	C33—C34—H34	119.8
C16—C15—C14	121.49 (16)	C36—C35—C34	122.02 (18)
C16—C15—H15	119.3	C36—C35—H35	119.0
C14—C15—H15	119.3	C34—C35—H35	119.0
C17—C16—C15	117.65 (16)	C37—C36—C35	117.12 (17)
C17—C16—C19	120.32 (18)	C37—C36—C39	121.3 (2)
C15—C16—C19	122.03 (17)	C35—C36—C39	121.6 (2)
C18—C17—C16	121.71 (16)	C36—C37—C38	121.81 (18)
C18—C17—H17	119.1	C36—C37—H37	119.1
C16—C17—H17	119.1	C38—C37—H37	119.1
C17—C18—C13	121.48 (15)	C37—C38—C33	121.66 (16)
C17—C18—H18	119.3	C37—C38—H38	119.2
C13—C18—H18	119.3	C33—C38—H38	119.2
C16—C19—H19A	109.5	C36—C39—H39A	109.5
C16—C19—H19B	109.5	C36—C39—H39B	109.5
H19A—C19—H19B	109.5	H39A—C39—H39B	109.5
C16—C19—H19C	109.5	C36—C39—H39C	109.5
H19A—C19—H19C	109.5	H39A—C39—H39C	109.5
H19B—C19—H19C	109.5	H39B—C39—H39C	109.5

C7'—C1—C2—C3	−178.61 (15)	C27'—C21—C22—C23	−175.12 (15)
C6—C1—C2—C3	3.6 (2)	C26—C21—C22—C23	0.3 (2)
C1—C2—C3—C11	−178.41 (14)	C21—C22—C23—C31	175.69 (13)
C1—C2—C3—C4	0.8 (2)	C21—C22—C23—C24	−2.1 (2)
C2—C3—C4—C5	23.3 (2)	C22—C23—C24—C25	−23.4 (2)
C11—C3—C4—C5	−157.48 (13)	C31—C23—C24—C25	158.86 (13)
C3—C4—C5—C6	−48.76 (17)	C23—C24—C25—C26	47.71 (17)
C3—C4—C5—C10	−167.69 (13)	C23—C24—C25—C30	−73.06 (16)
C3—C4—C5—C9	71.87 (17)	C23—C24—C25—C29	167.16 (12)
C7'—C1—C6—C5	150.42 (14)	C27'—C21—C26—C25	−157.49 (14)
C2—C1—C6—C5	−31.84 (18)	C22—C21—C26—C25	27.04 (19)
C4—C5—C6—C1	52.81 (17)	C24—C25—C26—C21	−49.54 (17)
C10—C5—C6—C1	172.48 (13)	C30—C25—C26—C21	71.34 (15)
C9—C5—C6—C1	−68.36 (15)	C29—C25—C26—C21	−169.52 (12)
C2—C1—C7'—C7	−177.09 (14)	C22—C21—C27'—C27	174.05 (15)
C6—C1—C7'—C7	0.6 (2)	C26—C21—C27'—C27	−1.2 (2)
C2—C1—C7'—C8	2.6 (2)	C22—C21—C27'—C28	−0.9 (2)
C6—C1—C7'—C8	−179.72 (15)	C26—C21—C27'—C28	−176.17 (15)
C2—C3—C11—C12	173.25 (16)	C22—C23—C31—C32	−178.41 (15)
C4—C3—C11—C12	−6.0 (2)	C24—C23—C31—C32	−0.7 (2)
C3—C11—C12—C13	−178.22 (14)	C23—C31—C32—C33	179.77 (14)
C11—C12—C13—C18	174.14 (16)	C31—C32—C33—C38	−179.65 (16)
C11—C12—C13—C14	−5.6 (2)	C31—C32—C33—C34	−0.3 (3)
C18—C13—C14—C15	−0.7 (2)	C38—C33—C34—C35	1.3 (2)
C12—C13—C14—C15	178.98 (14)	C32—C33—C34—C35	−178.10 (15)
C13—C14—C15—C16	0.6 (2)	C33—C34—C35—C36	0.5 (3)
C14—C15—C16—C17	0.2 (2)	C34—C35—C36—C37	−2.3 (3)
C14—C15—C16—C19	−179.42 (14)	C34—C35—C36—C39	175.55 (15)
C15—C16—C17—C18	−0.8 (2)	C35—C36—C37—C38	2.4 (3)
C19—C16—C17—C18	178.80 (14)	C39—C36—C37—C38	−175.46 (15)
C16—C17—C18—C13	0.7 (2)	C36—C37—C38—C33	−0.7 (3)
C14—C13—C18—C17	0.1 (2)	C34—C33—C38—C37	−1.2 (2)
C12—C13—C18—C17	−179.60 (14)	C32—C33—C38—C37	178.20 (15)

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀N₂
M_r	288.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	13.5270 (3), 16.1781 (3), 16.3616 (4)
β (°)	102.3807 (9)
V (Å³)	3497.32 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.50 × 0.40 × 0.32

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	62924, 7998, 2602
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.082, 0.96
No. of reflections	7998
No. of parameters	403
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.16

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1991), SHELXL97, PARST95 (Nardelli, 1995), PLATON (Spek, 2001).

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