PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1171.
Published online 2009 April 30. doi:  10.1107/S1600536809015311
PMCID: PMC2977836

1,2-Dimethyl-4,5-diphenyl­benzene determined on a Bruker SMART X2S benchtop crystallographic system

Abstract

The title compound, C20H18, has two crystallographically independent mol­ecules in the asymmetric unit. The phenyl substituents of mol­ecule A are twisted away from the plane defined by the central benzene ring by 131.8 (2) and −52.7 (3)°. The phenyl substituents of mol­ecule B are twisted by −133.3 (2) and 50.9 (3)°. Each mol­ecule is stabilized by a pair of intra­molecular C(aryl, sp 2)—H(...)π inter­actions, as well as by several inter­molecular C(methyl, sp 3)—H(...)π inter­actions.

Related literature

For potential applications and utility of the title compound as a synthetic inter­mediate, see: Kharasch et al. (1965 [triangle]); Horiuchi et al. (2008 [triangle]); Amine & Chen (2008 [triangle]); Eaton (2008 [triangle]); Peters & Friedrichsen (1995 [triangle]); Segura & Martín (1999 [triangle]). For the synthesis and related crystal structures, see: Maier et al., (1969 [triangle]); Maeyama & Yonezawa (2003 [triangle]); Brown & Levy (1979 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1171-scheme1.jpg

Experimental

Crystal data

  • C20H18
  • M r = 258.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1171-efi1.jpg
  • a = 9.3033 (7) Å
  • b = 10.7546 (9) Å
  • c = 16.3322 (12) Å
  • α = 93.793 (3)°
  • β = 98.934 (3)°
  • γ = 106.549 (2)°
  • V = 1536.8 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.06 mm−1
  • T = 296 K
  • 0.50 × 0.50 × 0.05 mm

Data collection

  • Bruker SMART X2S diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2007 [triangle]) T min = 0.969, T max = 0.997
  • 15460 measured reflections
  • 5450 independent reflections
  • 3881 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.166
  • S = 0.87
  • 5450 reflections
  • 365 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: GIS (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
C—H(...)π interaction geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015311/fl2245sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015311/fl2245Isup2.hkl

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

Acknowledgments

The authors thank the National Science Foundation for support of this work through the EPSCoR Research Infrastructure Improvement program (award No. 0432060) and The Center for High-rate Nanomanufacturing (CHN, award No. EEC-0425826). The authors also thank Dr Charles F. Campana and Scott Phillips of Bruker AXS for helpful discussions and training.

supplementary crystallographic information

Comment

o-Terphenyl has been utilized as a photochemical precursor to triphenylene (Kharasch et al., (1965)), as part of a cathode active material layer in battery applications (Horiuchi et al., (2008)), as a stabilizing additive in non-aqueous electrolytes (Amine & Chen, (2008)), and as a voltage stabilizer within the insulating layer of power cables (Eaton, (2008)). The title compound, an o-terphenyl derivative, is a potentially interesting synthetic intermediate leading to novel isobenzofuran (Peters & Friedrichsen, (1995)) and/or quinodimethane (Segura & Martín, (1999)) species and was first prepared in 1969 (Maier et al., (1969)). The synthesis of o-terphenyl derivatives was recently reviewed (Maeyama & Yonezawa, (2003)). A crystal structure of unsubstituted o-terphenyl has been published (Brown & Levy, (1979)).

The asymmetric unit of (I) contains two molecules (Fig. 1). The relative rotations of the phenyl substituents at C4 and C5 are influenced by a pair of stabilizing intramolecular C(aryl, sp2)-H···π interactions involving one ortho hydrogen atom on each phenyl substituent and one π bond associated with the ipso carbon of the other phenyl substituent (Fig. 2). The atoms of closest contact (Hortho—Cipso) are separated by 2.784 Å (Table 1). An MM2 force field minimization for a single molecule in a vacuum places the same two atoms 2.80 Å apart indicating that the molecular conformation within the crystal lattice is little influenced by packing forces. There are, e.g., no significant π-π interactions in the crystal structure.

Weaker intermolecular CH···π interactions involving both methyl substituents and π bonds on adjacent molecules help to define the spacing between molecules in the crystal structure (Table 1, Figs. 3–4). There are a total of five unique intermolecular CH···π interactions. Within the asymmetric unit, there is one intermolecular CH···π interaction (H8A1methyl···C16Bortho, 3.014 Å) involving one molecule A and one molecule B (A—B). Additionally, each molecule A and molecule B within the asymmetric unit has two unique CH···π interactions involving other molecules of the same type (2 A—A; 2 B—B). The two type A—A intermolecular CH···π interactions can be described as H7A2methyl-C5Acentral ring (2.892 Å) and H7A3methyl-C12Apara (2.920 Å). The two type B—B intermolecular CH···π interactions can be described as H7B1methyl-C11Bmeta (2.991 Å) and H8B1methyl-C12Bpara (2.943 Å). Figure 3 illustrates the one unique type A—B intermolecular CH···π interaction as well as one type A—A and one type B—B CH···π interaction.

Experimental

The title compound was prepared as illustrated in Fig. 5. An oven-dried glass pressure vessel containing a magnetic stir bar was charged with palladium(II) acetate (0.034 g, 0.152 mmol), 1,2-dibromo-4,5-dimethylbenzene (2 g, 7.58 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.124 g, 0.303 mmol), phenylboronic acid (2.77 g, 22.7 mmol) and powdered, anhydrous potassium phosphate (11.26 g, 53.0 mmol). Dry THF (20 ml) was added and N2 gas was bubbled through the resulting mixture for 15 min. The glass pressure vessel was sealed with a Teflon cap and heated at 75 °C for 20 h with stirring. The reaction mixture was allowed to cool to room temperature after which the mixture was diluted with diethyl ether (30 ml) and washed with water three times. The organic layer was dried over magnesium sulfate and concentrated at reduced pressure. The crude product was purified by flash column chromatography on silica gel using hexane-chloroform (80/20 v/v) as eluent. The title compound, 1,2-dimethyl-4,5-diphenylbenzene, was obtained in 76% isolated yield. 1H NMR (400 MHz, CDCl3) δ 2.35 (s, 6H), 7.11–7.21 (m, 12H); 13C NMR (100 MHz, CDCl3) δ 19.6 (CH3), 126.4 (CH), 128.0 (CH), 130.1 (CH), 132.1 (CH), 136.0 (C), 138.2 (C), 141.7 (C). An X-ray grade crystal was obtained by slow evaporation of a dichloromethane solution.

Figures

Fig. 1.
The molecular structure showing the crystallographic labelling scheme and displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radii.
Fig. 2.
Perspective view of the title molecule showing the two pairs of stabilizing intramolecular C(aryl, sp2)-H···π interactions involving one ortho hydrogen atom on each phenyl substituent and one π bond associated with ...
Fig. 3.
Perspective view of the title molecule showing stabilizing intermolecular C(methyl, sp3)-H···π interactions involving methyl substituents and π bonds associated with carbons of neighboring phenyl substituents. Molecule ...
Fig. 4.
Perspective view of long range packing in the crystal structure.
Fig. 5.
Synthesis of the title compound, 1,2-dimethyl-4,5-diphenylbenzene.

Crystal data

C20H18Z = 4
Mr = 258.34F(000) = 552
Triclinic, P1Dx = 1.117 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3033 (7) ÅCell parameters from 5281 reflections
b = 10.7546 (9) Åθ = 1.3–25.2°
c = 16.3322 (12) ŵ = 0.06 mm1
α = 93.793 (3)°T = 296 K
β = 98.934 (3)°Plate, clear colourless
γ = 106.549 (2)°0.50 × 0.50 × 0.05 mm
V = 1536.8 (2) Å3

Data collection

Bruker SMART X2S diffractometer5450 independent reflections
Radiation source: micro-focus sealed tube3881 reflections with I > 2σ(I)
doubly curved silicon crystalRint = 0.031
ω scansθmax = 25.2°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −11→11
Tmin = 0.969, Tmax = 0.997k = −12→12
15460 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 0.87w = 1/[σ2(Fo2) + (0.1P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3
5450 reflections(Δ/σ)max < 0.001
365 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.32 e Å3

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 (Å2)

xyzUiso*/Ueq
C1A0.6791 (2)1.08007 (18)0.97275 (13)0.0567 (5)
C2A0.6269 (2)1.01769 (19)0.89127 (13)0.0602 (5)
C3A0.6488 (2)0.89721 (19)0.87258 (12)0.0595 (5)
H3A0.61520.85660.81810.071*
C4A0.7186 (2)0.83381 (17)0.93120 (11)0.0527 (4)
C5A0.7660 (2)0.89453 (17)1.01371 (11)0.0507 (4)
C6A0.7463 (2)1.01665 (18)1.03178 (12)0.0555 (5)
H6A0.78001.05771.08620.067*
C7A0.6614 (3)1.2118 (2)0.99848 (16)0.0750 (6)
H7A10.69471.23381.05770.112*
H7A20.55621.20840.98400.112*
H7A30.72211.27680.97010.112*
C8A0.5478 (3)1.0778 (2)0.82374 (16)0.0822 (7)
H8A10.51301.01750.77370.123*
H8A20.61801.15700.81290.123*
H8A30.46231.09700.84180.123*
C9A0.7423 (2)0.70697 (18)0.90456 (11)0.0547 (5)
C10A0.6240 (3)0.6064 (2)0.85743 (14)0.0714 (6)
H10A0.52870.61840.84250.086*
C11A0.6455 (3)0.4888 (2)0.83227 (16)0.0858 (7)
H11A0.56450.42210.80130.103*
C12A0.7859 (3)0.4703 (2)0.85288 (15)0.0788 (7)
H12A0.80060.39150.83520.095*
C13A0.9046 (3)0.5682 (2)0.89956 (14)0.0703 (6)
H13A0.99960.55540.91420.084*
C14A0.8836 (2)0.6858 (2)0.92493 (12)0.0610 (5)
H14A0.96520.75190.95610.073*
C15A0.8283 (2)0.83145 (19)1.08364 (11)0.0543 (5)
C16A0.7485 (3)0.7074 (2)1.09899 (14)0.0686 (6)
H16A0.65610.66251.06460.082*
C17A0.8049 (3)0.6501 (3)1.16471 (17)0.0899 (8)
H17A0.75120.56671.17430.108*
C18A0.9418 (4)0.7172 (4)1.21634 (16)0.0999 (10)
H18A0.97970.67911.26100.120*
C19A1.0214 (3)0.8393 (3)1.20186 (15)0.0925 (8)
H19A1.11370.88371.23650.111*
C20A0.9653 (3)0.8970 (2)1.13604 (13)0.0712 (6)
H20A1.01970.98031.12690.085*
C1B0.2893 (2)1.2264 (2)0.56098 (18)0.0736 (6)
C2B0.3057 (3)1.2009 (2)0.47854 (18)0.0767 (7)
C3B0.2838 (2)1.0722 (2)0.44640 (15)0.0670 (6)
H3B0.29291.05540.39120.080*
C4B0.2488 (2)0.96758 (17)0.49331 (12)0.0534 (4)
C5B0.2360 (2)0.99418 (17)0.57707 (13)0.0549 (5)
C6B0.2545 (2)1.12292 (19)0.60791 (15)0.0670 (6)
H6B0.24291.14000.66270.080*
C7B0.3143 (3)1.3648 (2)0.6001 (2)0.1030 (10)
H7B10.42071.41240.60840.155*
H7B20.28081.36220.65280.155*
H7B30.25701.40730.56370.155*
C8B0.3495 (4)1.3080 (3)0.4225 (2)0.1211 (12)
H8B10.28071.35980.42150.182*
H8B20.34361.26920.36700.182*
H8B30.45171.36240.44370.182*
C9B0.2263 (2)0.83396 (17)0.45237 (11)0.0508 (4)
C10B0.3309 (2)0.8121 (2)0.40513 (13)0.0646 (5)
H10B0.41560.88090.40080.077*
C11B0.3109 (3)0.6904 (3)0.36479 (15)0.0773 (6)
H11B0.38150.67790.33310.093*
C12B0.1874 (3)0.5871 (2)0.37099 (14)0.0756 (7)
H12B0.17480.50490.34380.091*
C13B0.0818 (3)0.6059 (2)0.41787 (13)0.0683 (6)
H13B−0.00170.53630.42250.082*
C14B0.1012 (2)0.72904 (18)0.45784 (12)0.0586 (5)
H14B0.02950.74160.48870.070*
C15B0.2085 (2)0.89099 (18)0.63430 (12)0.0569 (5)
C16B0.2983 (3)0.8077 (2)0.64348 (13)0.0652 (5)
H16B0.37650.81570.61310.078*
C17B0.2728 (3)0.7128 (2)0.69743 (15)0.0832 (7)
H17B0.33360.65750.70280.100*
C18B0.1585 (4)0.7000 (3)0.74299 (16)0.0958 (9)
H18B0.14180.63600.77900.115*
C19B0.0694 (4)0.7813 (3)0.73542 (16)0.0950 (9)
H19B−0.00810.77250.76630.114*
C20B0.0939 (3)0.8768 (2)0.68189 (14)0.0762 (6)
H20B0.03300.93210.67760.091*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C1A0.0489 (10)0.0504 (10)0.0671 (12)0.0102 (8)0.0060 (9)0.0126 (9)
C2A0.0538 (11)0.0589 (11)0.0632 (12)0.0116 (9)0.0017 (9)0.0185 (9)
C3A0.0609 (12)0.0608 (12)0.0490 (10)0.0114 (9)−0.0011 (9)0.0083 (9)
C4A0.0492 (10)0.0530 (10)0.0511 (10)0.0094 (8)0.0043 (8)0.0095 (8)
C5A0.0452 (9)0.0532 (10)0.0506 (10)0.0110 (8)0.0045 (8)0.0102 (8)
C6A0.0526 (10)0.0544 (11)0.0526 (10)0.0096 (8)0.0024 (8)0.0044 (8)
C7A0.0728 (14)0.0597 (13)0.0910 (16)0.0206 (11)0.0075 (12)0.0120 (11)
C8A0.0858 (16)0.0770 (15)0.0801 (15)0.0267 (13)−0.0071 (13)0.0244 (12)
C9A0.0594 (11)0.0552 (11)0.0475 (10)0.0132 (9)0.0098 (8)0.0100 (8)
C10A0.0699 (13)0.0681 (13)0.0691 (13)0.0176 (11)0.0023 (11)−0.0036 (11)
C11A0.0900 (18)0.0720 (15)0.0832 (16)0.0149 (13)0.0075 (13)−0.0150 (12)
C12A0.1027 (19)0.0640 (14)0.0766 (15)0.0291 (13)0.0306 (14)0.0039 (11)
C13A0.0769 (14)0.0765 (14)0.0696 (13)0.0319 (12)0.0289 (12)0.0176 (11)
C14A0.0615 (12)0.0629 (12)0.0588 (11)0.0156 (9)0.0157 (9)0.0114 (9)
C15A0.0542 (11)0.0673 (12)0.0469 (10)0.0264 (9)0.0088 (8)0.0091 (9)
C16A0.0686 (13)0.0759 (14)0.0676 (13)0.0271 (11)0.0139 (10)0.0252 (11)
C17A0.101 (2)0.107 (2)0.0881 (18)0.0555 (17)0.0322 (16)0.0513 (16)
C18A0.113 (2)0.161 (3)0.0649 (15)0.090 (2)0.0245 (16)0.0473 (18)
C19A0.0822 (17)0.145 (3)0.0585 (14)0.0564 (18)−0.0049 (12)0.0087 (16)
C20A0.0644 (13)0.0904 (16)0.0576 (12)0.0285 (12)−0.0011 (10)0.0046 (11)
C1B0.0521 (12)0.0495 (11)0.119 (2)0.0181 (9)0.0116 (12)0.0077 (12)
C2B0.0601 (13)0.0559 (12)0.115 (2)0.0187 (10)0.0071 (13)0.0307 (13)
C3B0.0625 (12)0.0623 (13)0.0765 (14)0.0185 (10)0.0085 (10)0.0205 (10)
C4B0.0445 (10)0.0502 (10)0.0649 (12)0.0148 (8)0.0052 (8)0.0111 (9)
C5B0.0465 (10)0.0493 (10)0.0678 (12)0.0137 (8)0.0096 (9)0.0032 (9)
C6B0.0566 (12)0.0540 (12)0.0895 (15)0.0153 (9)0.0173 (11)−0.0022 (11)
C7B0.0788 (16)0.0497 (13)0.178 (3)0.0202 (12)0.0189 (18)−0.0019 (15)
C8B0.133 (3)0.0742 (17)0.164 (3)0.0323 (17)0.028 (2)0.0610 (19)
C9B0.0499 (10)0.0542 (10)0.0473 (10)0.0179 (8)0.0008 (8)0.0089 (8)
C10B0.0574 (12)0.0755 (14)0.0597 (12)0.0216 (10)0.0056 (9)0.0042 (10)
C11B0.0712 (15)0.0945 (17)0.0694 (14)0.0399 (14)0.0012 (11)−0.0092 (12)
C12B0.0977 (18)0.0681 (14)0.0625 (13)0.0447 (14)−0.0140 (12)−0.0042 (11)
C13B0.0821 (15)0.0544 (12)0.0576 (12)0.0139 (10)−0.0080 (11)0.0087 (9)
C14B0.0613 (12)0.0579 (11)0.0529 (11)0.0146 (9)0.0049 (9)0.0074 (9)
C15B0.0603 (11)0.0493 (10)0.0524 (10)0.0073 (9)0.0053 (9)−0.0031 (8)
C16B0.0709 (13)0.0606 (12)0.0592 (12)0.0185 (10)0.0007 (10)0.0040 (10)
C17B0.109 (2)0.0675 (14)0.0639 (14)0.0247 (13)−0.0077 (14)0.0088 (11)
C18B0.134 (3)0.0789 (17)0.0597 (14)0.0105 (17)0.0105 (16)0.0154 (12)
C19B0.115 (2)0.0932 (19)0.0661 (15)0.0049 (17)0.0355 (15)0.0097 (14)
C20B0.0830 (15)0.0723 (14)0.0707 (14)0.0155 (12)0.0243 (12)−0.0002 (11)

Geometric parameters (Å, °)

C1A—C6A1.389 (3)C1B—C6B1.384 (3)
C1A—C2A1.397 (3)C1B—C2B1.397 (4)
C1A—C7A1.512 (3)C1B—C7B1.519 (3)
C2A—C3A1.390 (3)C2B—C3B1.394 (3)
C2A—C8A1.513 (3)C2B—C8B1.522 (3)
C3A—C4A1.396 (3)C3B—C4B1.394 (3)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.404 (3)C4B—C5B1.409 (3)
C4A—C9A1.491 (3)C4B—C9B1.488 (3)
C5A—C6A1.396 (3)C5B—C6B1.395 (3)
C5A—C15A1.491 (3)C5B—C15B1.490 (3)
C6A—H6A0.9300C6B—H6B0.9300
C7A—H7A10.9600C7B—H7B10.9600
C7A—H7A20.9600C7B—H7B20.9600
C7A—H7A30.9600C7B—H7B30.9600
C8A—H8A10.9600C8B—H8B10.9600
C8A—H8A20.9600C8B—H8B20.9600
C8A—H8A30.9600C8B—H8B30.9600
C9A—C10A1.386 (3)C9B—C14B1.391 (3)
C9A—C14A1.391 (3)C9B—C10B1.391 (3)
C10A—C11A1.382 (3)C10B—C11B1.375 (3)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.371 (4)C11B—C12B1.374 (3)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.371 (3)C12B—C13B1.385 (3)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.381 (3)C13B—C14B1.388 (3)
C13A—H13A0.9300C13B—H13B0.9300
C14A—H14A0.9300C14B—H14B0.9300
C15A—C20A1.386 (3)C15B—C16B1.389 (3)
C15A—C16A1.390 (3)C15B—C20B1.394 (3)
C16A—C17A1.380 (3)C16B—C17B1.386 (3)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.384 (4)C17B—C18B1.371 (4)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.367 (4)C18B—C19B1.364 (4)
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.383 (3)C19B—C20B1.385 (3)
C19A—H19A0.9300C19B—H19B0.9300
C20A—H20A0.9300C20B—H20B0.9300
C6A—C1A—C2A118.28 (18)C6B—C1B—C2B118.5 (2)
C6A—C1A—C7A119.56 (18)C6B—C1B—C7B120.1 (3)
C2A—C1A—C7A122.15 (18)C2B—C1B—C7B121.3 (2)
C3A—C2A—C1A118.55 (17)C3B—C2B—C1B118.8 (2)
C3A—C2A—C8A119.69 (19)C3B—C2B—C8B118.4 (3)
C1A—C2A—C8A121.76 (19)C1B—C2B—C8B122.8 (2)
C2A—C3A—C4A123.52 (18)C2B—C3B—C4B123.0 (2)
C2A—C3A—H3A118.2C2B—C3B—H3B118.5
C4A—C3A—H3A118.2C4B—C3B—H3B118.5
C3A—C4A—C5A117.80 (17)C3B—C4B—C5B118.06 (18)
C3A—C4A—C9A119.66 (17)C3B—C4B—C9B118.42 (18)
C5A—C4A—C9A122.53 (16)C5B—C4B—C9B123.52 (16)
C6A—C5A—C4A118.40 (16)C6B—C5B—C4B118.42 (18)
C6A—C5A—C15A118.50 (16)C6B—C5B—C15B119.01 (18)
C4A—C5A—C15A123.02 (16)C4B—C5B—C15B122.54 (16)
C1A—C6A—C5A123.39 (18)C1B—C6B—C5B123.2 (2)
C1A—C6A—H6A118.3C1B—C6B—H6B118.4
C5A—C6A—H6A118.3C5B—C6B—H6B118.4
C1A—C7A—H7A1109.5C1B—C7B—H7B1109.5
C1A—C7A—H7A2109.5C1B—C7B—H7B2109.5
H7A1—C7A—H7A2109.5H7B1—C7B—H7B2109.5
C1A—C7A—H7A3109.5C1B—C7B—H7B3109.5
H7A1—C7A—H7A3109.5H7B1—C7B—H7B3109.5
H7A2—C7A—H7A3109.5H7B2—C7B—H7B3109.5
C2A—C8A—H8A1109.5C2B—C8B—H8B1109.5
C2A—C8A—H8A2109.5C2B—C8B—H8B2109.5
H8A1—C8A—H8A2109.5H8B1—C8B—H8B2109.5
C2A—C8A—H8A3109.5C2B—C8B—H8B3109.5
H8A1—C8A—H8A3109.5H8B1—C8B—H8B3109.5
H8A2—C8A—H8A3109.5H8B2—C8B—H8B3109.5
C10A—C9A—C14A117.72 (19)C14B—C9B—C10B118.09 (18)
C10A—C9A—C4A120.83 (18)C14B—C9B—C4B122.16 (17)
C14A—C9A—C4A121.45 (17)C10B—C9B—C4B119.72 (17)
C11A—C10A—C9A121.1 (2)C11B—C10B—C9B121.0 (2)
C11A—C10A—H10A119.5C11B—C10B—H10B119.5
C9A—C10A—H10A119.5C9B—C10B—H10B119.5
C12A—C11A—C10A120.2 (2)C10B—C11B—C12B120.5 (2)
C12A—C11A—H11A119.9C10B—C11B—H11B119.7
C10A—C11A—H11A119.9C12B—C11B—H11B119.7
C13A—C12A—C11A119.8 (2)C11B—C12B—C13B119.7 (2)
C13A—C12A—H12A120.1C11B—C12B—H12B120.1
C11A—C12A—H12A120.1C13B—C12B—H12B120.1
C12A—C13A—C14A120.2 (2)C12B—C13B—C14B119.7 (2)
C12A—C13A—H13A119.9C12B—C13B—H13B120.1
C14A—C13A—H13A119.9C14B—C13B—H13B120.1
C13A—C14A—C9A121.0 (2)C13B—C14B—C9B120.9 (2)
C13A—C14A—H14A119.5C13B—C14B—H14B119.5
C9A—C14A—H14A119.5C9B—C14B—H14B119.5
C20A—C15A—C16A118.71 (19)C16B—C15B—C20B117.8 (2)
C20A—C15A—C5A120.54 (18)C16B—C15B—C5B121.12 (18)
C16A—C15A—C5A120.72 (18)C20B—C15B—C5B121.11 (19)
C17A—C16A—C15A120.7 (2)C17B—C16B—C15B120.7 (2)
C17A—C16A—H16A119.7C17B—C16B—H16B119.6
C15A—C16A—H16A119.7C15B—C16B—H16B119.6
C16A—C17A—C18A119.7 (3)C18B—C17B—C16B120.4 (3)
C16A—C17A—H17A120.1C18B—C17B—H17B119.8
C18A—C17A—H17A120.1C16B—C17B—H17B119.8
C19A—C18A—C17A120.1 (2)C19B—C18B—C17B119.9 (3)
C19A—C18A—H18A119.9C19B—C18B—H18B120.0
C17A—C18A—H18A119.9C17B—C18B—H18B120.0
C18A—C19A—C20A120.3 (3)C18B—C19B—C20B120.3 (3)
C18A—C19A—H19A119.8C18B—C19B—H19B119.8
C20A—C19A—H19A119.8C20B—C19B—H19B119.8
C19A—C20A—C15A120.4 (2)C19B—C20B—C15B120.9 (2)
C19A—C20A—H20A119.8C19B—C20B—H20B119.6
C15A—C20A—H20A119.8C15B—C20B—H20B119.6
C6A—C1A—C2A—C3A−1.9 (3)C6B—C1B—C2B—C3B1.2 (3)
C7A—C1A—C2A—C3A179.46 (18)C7B—C1B—C2B—C3B179.0 (2)
C6A—C1A—C2A—C8A178.02 (19)C6B—C1B—C2B—C8B−177.7 (2)
C7A—C1A—C2A—C8A−0.6 (3)C7B—C1B—C2B—C8B0.1 (4)
C1A—C2A—C3A—C4A0.9 (3)C1B—C2B—C3B—C4B−1.2 (3)
C8A—C2A—C3A—C4A−179.04 (19)C8B—C2B—C3B—C4B177.7 (2)
C2A—C3A—C4A—C5A1.3 (3)C2B—C3B—C4B—C5B−0.3 (3)
C2A—C3A—C4A—C9A−177.72 (18)C2B—C3B—C4B—C9B179.45 (18)
C3A—C4A—C5A—C6A−2.5 (3)C3B—C4B—C5B—C6B1.9 (3)
C9A—C4A—C5A—C6A176.55 (16)C9B—C4B—C5B—C6B−177.88 (17)
C3A—C4A—C5A—C15A174.07 (17)C3B—C4B—C5B—C15B−176.16 (18)
C9A—C4A—C5A—C15A−6.9 (3)C9B—C4B—C5B—C15B4.1 (3)
C2A—C1A—C6A—C5A0.7 (3)C2B—C1B—C6B—C5B0.5 (3)
C7A—C1A—C6A—C5A179.40 (18)C7B—C1B—C6B—C5B−177.4 (2)
C4A—C5A—C6A—C1A1.5 (3)C4B—C5B—C6B—C1B−2.0 (3)
C15A—C5A—C6A—C1A−175.20 (17)C15B—C5B—C6B—C1B176.11 (19)
C3A—C4A—C9A—C10A−49.2 (3)C3B—C4B—C9B—C14B−131.5 (2)
C5A—C4A—C9A—C10A131.8 (2)C5B—C4B—C9B—C14B48.3 (3)
C3A—C4A—C9A—C14A129.9 (2)C3B—C4B—C9B—C10B46.9 (2)
C5A—C4A—C9A—C14A−49.1 (3)C5B—C4B—C9B—C10B−133.3 (2)
C14A—C9A—C10A—C11A0.6 (3)C14B—C9B—C10B—C11B0.2 (3)
C4A—C9A—C10A—C11A179.7 (2)C4B—C9B—C10B—C11B−178.27 (18)
C9A—C10A—C11A—C12A−0.8 (4)C9B—C10B—C11B—C12B−0.6 (3)
C10A—C11A—C12A—C13A0.9 (4)C10B—C11B—C12B—C13B0.4 (3)
C11A—C12A—C13A—C14A−0.8 (3)C11B—C12B—C13B—C14B0.3 (3)
C12A—C13A—C14A—C9A0.6 (3)C12B—C13B—C14B—C9B−0.8 (3)
C10A—C9A—C14A—C13A−0.5 (3)C10B—C9B—C14B—C13B0.5 (3)
C4A—C9A—C14A—C13A−179.64 (17)C4B—C9B—C14B—C13B178.92 (17)
C6A—C5A—C15A—C20A−54.4 (2)C6B—C5B—C15B—C16B−127.1 (2)
C4A—C5A—C15A—C20A129.1 (2)C4B—C5B—C15B—C16B50.9 (3)
C6A—C5A—C15A—C16A123.8 (2)C6B—C5B—C15B—C20B51.4 (3)
C4A—C5A—C15A—C16A−52.7 (3)C4B—C5B—C15B—C20B−130.5 (2)
C20A—C15A—C16A—C17A−0.5 (3)C20B—C15B—C16B—C17B0.8 (3)
C5A—C15A—C16A—C17A−178.7 (2)C5B—C15B—C16B—C17B179.38 (18)
C15A—C16A—C17A—C18A0.5 (4)C15B—C16B—C17B—C18B−0.3 (3)
C16A—C17A—C18A—C19A−0.5 (4)C16B—C17B—C18B—C19B−0.2 (4)
C17A—C18A—C19A—C20A0.5 (4)C17B—C18B—C19B—C20B0.0 (4)
C18A—C19A—C20A—C15A−0.5 (4)C18B—C19B—C20B—C15B0.6 (4)
C16A—C15A—C20A—C19A0.5 (3)C16B—C15B—C20B—C19B−1.0 (3)
C5A—C15A—C20A—C19A178.7 (2)C5B—C15B—C20B—C19B−179.6 (2)

Table 1 C—H···π interaction geometry (Å, °)

C–H···πC–HH···πC···πC–H···π
C7A—H7A2···C5A0.962.8923.780154.41
C7A—H7A3···C12A0.962.9203.824157.38
C8A—H8A1···C16B0.963.0143.924158.82
C14A—H14A···C15A0.932.8113.126101.09
C16A—H16A···C9A0.932.8813.16799.24
C7B—H7B1···C11B0.962.9913.666128.53
C8B—H8B1···C12B0.962.9433.809150.67
C14B—H14B···C15B0.932.7843.129103.11
C16B—H16B···C9B0.932.8233.138101.13

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2245).

References

  • Amine, K. & Chen, Z. (2008). US Patent Appl. US 2007-767114.
  • Brown, G. M. & Levy, H. A. (1979). Acta Cryst. B35, 785–788.
  • Bruker (2007). APEX2, GIS, SADABS and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Eaton, R. F. (2008). PCT Int. Appl. WO, 2008112965.
  • Horiuchi, H., Tanaka, T. & Soma, M. (2008). US Patent Appl. US 2008-136831.
  • Kharasch, N., Alston, T. G., Lewis, H. B. & Wolf, W. (1965). Chem. Commun. pp. 242–243.
  • Maeyama, K. & Yonezawa, N. (2003). Recent. Res. Dev. Org. Chem., 7, 53–61.
  • Maier, G., Heep, U., Wiessler, M. & Strasser, M. (1969). Chem. Ber.102, 1928–1936.
  • Peters, O. & Friedrichsen, W. (1995). Trends Heterocycl. Chem.4, 217–259.
  • Segura, J. L. & Martín, N. (1999). Chem. Rev.99, 3199–3246. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography