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In the title compound, C30H22, the bi­phenyl and naphthyl substituents are each planar to within 0.03 Å. They extend from the cubane like the wings of a butterfly, with a slight dihedral angle of 9.4 (2)° between their planes. In the crystal structure, the naphthyl groups form close-packed stacks, with cubyls and bi­phenyls extending alternately to the right and the left.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017483/ob6273sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017483/ob6273Isup2.hkl
Contains datablock I

CCDC reference: 222856

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.062
  • wR factor = 0.168
  • Data-to-parameter ratio = 7.3

checkCIF/PLATON results

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Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda -0.2133 Proportion of unique data used 1.0000 Ratio reflections to parameters 7.3297 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ... 7.33 PLAT320_ALERT_2_C Check Hybridisation of C1 in Main Residue ? PLAT320_ALERT_2_C Check Hybridisation of C3 in Main Residue ? PLAT320_ALERT_2_C Check Hybridisation of C4 in Main Residue ? PLAT320_ALERT_2_C Check Hybridisation of C5 in Main Residue ? PLAT320_ALERT_2_C Check Hybridisation of C7 in Main Residue ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang.. 8 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ...... 16
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 68.78 From the CIF: _reflns_number_total 2001 Count of symmetry unique reflns 2002 Completeness (_total/calc) 99.95% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title molecule, (I), was synthesized by Eaton et al. (1999) along with 1-(p-biphenyl)-4'-(2-naphthyl)-p-[2]cubyl, and a series of other polycubyl molecules to study the properties of cubanes that are linked together at the 1 and 4 positions. Because poly-1,4-cubanes are semi-rigid rod-like structures, the distances between two terminal substituents are fixed, even in solution, making them useful for studying the distance dependence of intramolecular electron-transfer reactions. Paulson et al. (1993) studied the electron-transfer reaction of the title compound by irradiating the molecules (in solution) with high-energy electrons and photometrically observing electron transfer in the anionic form of (I). They found that using cubane as a spacer enhanced the electron transfer rate between the biphenyl and naphthyl groups. Compared to the electron transfer between the same substituents on cyclohexane spacers, the rate of transfer was measured to be 10±3 times larger for the cubane compound. Stronger bond-to-bond couplings and a larger number of pathways are offered as explanations for the enhanced coupling through cubane spacers. Increasing the distance by doubling or tripling the number of cubyl or cyclohexyl spacers leads to an exponential decline in transfer rate with distance; the fall-off with distance was similar for both types of spacer.

The biphenyl groups of (I) are nearly planar, with all C atoms fitting a least-squares plane to within a full range of ±0.031 Å (Fig. 1 and Table 1). The average torsion angle of the biphenyl linkage is 2.1°, versus an average of 23.4° for 772 similar biphenyl linkages (all those with four H atoms adjacent to the central linkage bond) found in the Cambridge Structural Database (Version 5.24; Allen, 2002). The naphthyl groups are even more closely planar; their C atoms fit a least-squares plane to within ±0.007 Å.

The title molecule, (I), has a complex supramolecular assembly. Looking down the a axis (Fig. 2), one can see stacks of intercalated biphenyl groups at the ends of the cell, and a close-packed stack of naphthyl substituents in the center of the cell. There is a twofold screw axis along b which goes through the central naphthyl stack. Fig. 3 illustrates an end-on view of a naphthyl stack, showing that is actually a herring-bone stack, not a stack wherein all planes are parallel. Despite the presence of the close-packed naphthyl stacks and slightly looser biphenyl stacks there are no intermolecular contacts that are significantly less than the sum of van der Waals radii.

Experimental top

The crystals were provided by Philip Eaton and Todd Emrick of the University of Chicago. Details of the synthesis of the title molecule, (I), from 1,4-diiodocubane, p-biphenyllithium and naphthalene-1,4-oxide were reported by Eaton et al. (1999). Crystals were grown by slow evaporation from an n-octane solution.

Refinement top

Although the space group is acentric, with Mo Kα radiation and only carbon and hydrogen elements there is no basis for determining the absolute configuration. Friedel equivalents were merged, and the `handedness' displayed by the structure (if any) is purely arbitrary. The Flack (1983) parameter, before merging, refined to a value of 2(5). All H atoms were found in difference Fourier maps, but during the refinement they were placed at ideal (SHELXTL) tetrahedral or trigonal positions. They were riding on their bonded neighbors during the refinement, with periodic reidealization, and their displacement parameters were set to be isotropic, with a value equal to 1.2Ueq of the neighboring C atom.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 25% probability level.
[Figure 2] Fig. 2. A packing diagram of (I), looking down the short a axis, illustrating the close-packed naphthyl groups and the intercalated biphenyl groups.
[Figure 3] Fig. 3. A space-filled diagram illustrating an edge-on view of the close-packed stacks of naphthyl groups. The biphenyl rings have been omitted for clarity and the cubanes are represented by large labeled spheres.
1-(p-biphenyl)-4'-(2-napthyl)cubane top
Crystal data top
C30H22F(000) = 404
Mr = 382.48Dx = 1.276 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 22 reflections
a = 5.9788 (4) Åθ = 6.2–42.2°
b = 7.579 (1) ŵ = 0.55 mm1
c = 22.044 (1) ÅT = 294 K
β = 94.570 (8)°Thin lath, colorless
V = 995.71 (15) Å30.52 × 0.16 × 0.02 mm
Z = 2
Data collection top
Siemens P4
diffractometer
1271 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 68.8°, θmin = 4.0°
ω scansh = 77
Absorption correction: integration
(Wuensch et al., 1965)
k = 91
Tmin = 0.847, Tmax = 0.988l = 026
2001 measured reflections3 standard reflections every 97 reflections
2001 independent reflections intensity decay: none
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062 w = 1/[σ2(Fo2) + (0.0582P)2 + 0.2164P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.168(Δ/σ)max = 0.002
S = 1.08Δρmax = 0.17 e Å3
2001 reflectionsΔρmin = 0.19 e Å3
273 parametersExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
7 restraintsExtinction coefficient: 0.0034 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: see text
Secondary atom site location: structure-invariant direct methods
Crystal data top
C30H22V = 995.71 (15) Å3
Mr = 382.48Z = 2
Monoclinic, P21Cu Kα radiation
a = 5.9788 (4) ŵ = 0.55 mm1
b = 7.579 (1) ÅT = 294 K
c = 22.044 (1) Å0.52 × 0.16 × 0.02 mm
β = 94.570 (8)°
Data collection top
Siemens P4
diffractometer
1271 reflections with I > 2σ(I)
Absorption correction: integration
(Wuensch et al., 1965)
Rint = 0.038
Tmin = 0.847, Tmax = 0.9883 standard reflections every 97 reflections
2001 measured reflections intensity decay: none
2001 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0627 restraints
wR(F2) = 0.168H-atom parameters constrained
S = 1.08Δρmax = 0.17 e Å3
2001 reflectionsΔρmin = 0.19 e Å3
273 parametersAbsolute structure: see text
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 > 2σ(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
xyzUiso*/Ueq
C11.1372 (9)0.8394 (10)0.3325 (2)0.0527 (15)
C21.1800 (12)0.6999 (11)0.2828 (3)0.073 (2)
H2A1.25730.58720.29060.088*
C31.2549 (10)0.8428 (11)0.2393 (2)0.0686 (19)
H3A1.38880.83650.21650.082*
C41.0094 (10)0.8620 (10)0.2106 (2)0.0548 (15)
C50.9345 (12)0.7187 (10)0.2554 (3)0.070 (2)
H5A0.83340.62020.24420.084*
C60.8926 (9)0.8608 (13)0.3032 (3)0.068 (2)
H6A0.75880.86690.32600.081*
C70.9657 (11)1.0056 (10)0.2597 (3)0.0657 (19)
H7A0.88841.11820.25170.079*
C81.2112 (12)0.9841 (10)0.2875 (3)0.0658 (19)
H8A1.31261.08230.29900.079*
C1A0.7824 (9)0.8760 (9)0.0197 (2)0.0490 (13)
C2A0.9826 (10)0.7938 (9)0.0406 (2)0.0619 (18)
H2AA1.06800.73740.01290.074*
C3A1.0565 (11)0.7943 (9)0.1014 (2)0.0627 (18)
H3AA1.19190.73950.11360.075*
C4A0.9363 (10)0.8737 (10)0.1450 (2)0.0553 (16)
C5A0.7383 (10)0.9570 (10)0.1244 (3)0.0634 (18)
H5AA0.65441.01480.15210.076*
C6A0.6633 (10)0.9557 (10)0.0635 (3)0.0608 (18)
H6AA0.52761.01030.05160.073*
C1B0.6999 (9)0.8777 (8)0.0457 (2)0.0478 (13)
C2B0.8221 (12)0.8024 (10)0.0894 (3)0.074 (2)
H2BA0.95910.74940.07770.089*
C3B0.7447 (12)0.8043 (12)0.1505 (3)0.086 (3)
H3BA0.82920.75070.17900.103*
C4B0.5461 (12)0.8839 (12)0.1693 (3)0.077 (2)
H4BA0.49640.88840.21030.092*
C5B0.4242 (12)0.9556 (11)0.1269 (3)0.079 (2)
H5BA0.28701.00780.13880.095*
C6B0.4978 (10)0.9533 (10)0.0663 (3)0.0665 (19)
H6BA0.40901.00420.03830.080*
C1C1.0753 (9)0.8718 (9)0.4430 (2)0.0485 (14)
H1CA0.93580.92190.43210.058*
C2C1.2093 (9)0.8218 (8)0.3984 (2)0.0485 (15)
C3C1.4193 (9)0.7448 (9)0.4153 (3)0.0584 (17)
H3CA1.51010.70890.38530.070*
C4C1.4920 (10)0.7219 (8)0.4749 (3)0.0546 (15)
H4CA1.63280.67310.48490.065*
C5C1.4256 (10)0.7481 (8)0.5842 (2)0.0585 (17)
H5CA1.56430.69750.59550.070*
C6C1.2907 (11)0.7991 (11)0.6277 (3)0.069 (2)
H6CA1.33820.78390.66860.083*
C7C1.0822 (10)0.8738 (10)0.6116 (2)0.0637 (17)
H7CA0.99040.90620.64190.076*
C8C1.0104 (10)0.9003 (9)0.5520 (2)0.0548 (16)
H8CA0.87170.95280.54200.066*
C9C1.1454 (8)0.8485 (8)0.5053 (2)0.0417 (12)
C10C1.3566 (9)0.7712 (8)0.5214 (2)0.0481 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.060 (3)0.056 (4)0.043 (3)0.007 (4)0.010 (3)0.001 (3)
C20.103 (6)0.067 (4)0.050 (4)0.011 (4)0.011 (4)0.001 (3)
C30.072 (4)0.090 (5)0.047 (3)0.006 (4)0.020 (3)0.001 (4)
C40.069 (4)0.057 (4)0.039 (3)0.003 (4)0.012 (3)0.003 (3)
C50.095 (5)0.068 (5)0.047 (4)0.025 (4)0.001 (3)0.002 (3)
C60.056 (3)0.102 (6)0.048 (3)0.008 (5)0.018 (3)0.006 (4)
C70.087 (5)0.065 (4)0.046 (3)0.018 (4)0.007 (3)0.002 (3)
C80.088 (5)0.069 (4)0.040 (3)0.024 (4)0.003 (3)0.000 (3)
C1A0.058 (3)0.046 (3)0.044 (3)0.000 (3)0.013 (2)0.004 (3)
C2A0.071 (4)0.067 (4)0.047 (3)0.024 (4)0.007 (3)0.005 (3)
C3A0.077 (4)0.065 (4)0.047 (3)0.021 (4)0.008 (3)0.000 (3)
C4A0.067 (4)0.058 (4)0.043 (3)0.002 (4)0.014 (3)0.001 (3)
C5A0.061 (4)0.084 (5)0.048 (3)0.004 (4)0.021 (3)0.007 (4)
C6A0.054 (3)0.076 (5)0.054 (3)0.017 (4)0.011 (3)0.003 (3)
C1B0.051 (3)0.042 (3)0.051 (3)0.003 (3)0.006 (2)0.003 (3)
C2B0.083 (5)0.086 (6)0.053 (3)0.020 (4)0.001 (3)0.009 (4)
C3B0.099 (5)0.111 (7)0.046 (3)0.020 (5)0.002 (3)0.018 (4)
C4B0.086 (5)0.079 (6)0.063 (4)0.006 (5)0.017 (4)0.001 (4)
C5B0.073 (4)0.092 (6)0.072 (4)0.016 (5)0.006 (4)0.014 (4)
C6B0.065 (4)0.082 (5)0.052 (3)0.018 (4)0.007 (3)0.007 (4)
C1C0.048 (3)0.052 (4)0.046 (3)0.003 (3)0.006 (2)0.001 (3)
C2C0.050 (3)0.054 (4)0.042 (3)0.006 (3)0.008 (2)0.005 (3)
C3C0.053 (3)0.065 (5)0.060 (4)0.010 (3)0.017 (3)0.007 (3)
C4C0.050 (3)0.051 (4)0.063 (4)0.002 (3)0.006 (3)0.003 (3)
C5C0.062 (4)0.057 (4)0.055 (3)0.005 (4)0.008 (3)0.010 (3)
C6C0.078 (4)0.084 (6)0.044 (3)0.001 (4)0.001 (3)0.015 (4)
C7C0.071 (4)0.077 (5)0.044 (3)0.001 (4)0.010 (3)0.000 (4)
C8C0.055 (3)0.064 (4)0.046 (3)0.005 (3)0.006 (2)0.004 (3)
C9C0.044 (3)0.041 (3)0.041 (3)0.002 (3)0.001 (2)0.001 (3)
C10C0.046 (3)0.046 (3)0.052 (3)0.003 (3)0.000 (2)0.003 (3)
Geometric parameters (Å, º) top
C1—C2C1.487 (7)C6A—H6AA0.9300
C1—C21.559 (9)C1B—C2B1.378 (8)
C1—C61.560 (8)C1B—C6B1.381 (7)
C1—C81.566 (9)C2B—C3B1.390 (7)
C2—C31.535 (9)C2B—H2BA0.9300
C2—C51.549 (10)C3B—C4B1.366 (9)
C2—H2A0.9800C3B—H3BA0.9300
C3—C81.546 (9)C4B—C5B1.345 (9)
C3—C41.559 (8)C4B—H4BA0.9300
C3—H3A0.9800C5B—C6B1.373 (8)
C4—C4A1.480 (7)C5B—H5BA0.9300
C4—C51.558 (9)C6B—H6BA0.9300
C4—C71.573 (9)C1C—C2C1.370 (7)
C5—C61.540 (10)C1C—C9C1.415 (6)
C5—H5A0.9800C1C—H1CA0.9300
C6—C71.542 (10)C2C—C3C1.408 (8)
C6—H6A0.9800C3C—C4C1.360 (7)
C7—C81.553 (9)C3C—H3CA0.9300
C7—H7A0.9800C4C—C10C1.407 (7)
C8—H8A0.9800C4C—H4CA0.9300
C1A—C6A1.385 (7)C5C—C6C1.359 (8)
C1A—C2A1.395 (8)C5C—C10C1.423 (7)
C1A—C1B1.485 (7)C5C—H5CA0.9300
C2A—C3A1.378 (7)C6C—C7C1.389 (8)
C2A—H2AA0.9300C6C—H6CA0.9300
C3A—C4A1.382 (7)C7C—C8C1.365 (7)
C3A—H3AA0.9300C7C—H7CA0.9300
C4A—C5A1.386 (8)C8C—C9C1.414 (7)
C5A—C6A1.380 (7)C8C—H8CA0.9300
C5A—H5AA0.9300C9C—C10C1.411 (7)
C2C—C1—C2125.1 (6)C3A—C4A—C5A116.7 (5)
C2C—C1—C6127.1 (5)C3A—C4A—C4121.6 (6)
C2—C1—C688.8 (5)C5A—C4A—C4121.7 (5)
C2C—C1—C8127.3 (6)C6A—C5A—C4A121.2 (6)
C2—C1—C887.6 (4)C6A—C5A—H5AA119.4
C6—C1—C888.1 (5)C4A—C5A—H5AA119.4
C3—C2—C590.4 (5)C5A—C6A—C1A122.5 (6)
C3—C2—C191.9 (6)C5A—C6A—H6AA118.8
C5—C2—C190.5 (5)C1A—C6A—H6AA118.8
C3—C2—H2A124.6C2B—C1B—C6B116.2 (5)
C5—C2—H2A124.6C2B—C1B—C1A121.4 (5)
C1—C2—H2A124.6C6B—C1B—C1A122.4 (5)
C2—C3—C889.2 (4)C1B—C2B—C3B121.3 (7)
C2—C3—C490.4 (5)C1B—C2B—H2BA119.4
C8—C3—C490.5 (5)C3B—C2B—H2BA119.4
C2—C3—H3A125.2C4B—C3B—C2B120.8 (7)
C8—C3—H3A125.2C4B—C3B—H3BA119.6
C4—C3—H3A125.2C2B—C3B—H3BA119.6
C4A—C4—C5125.7 (6)C5B—C4B—C3B118.3 (7)
C4A—C4—C3126.8 (5)C5B—C4B—H4BA120.8
C5—C4—C389.2 (5)C3B—C4B—H4BA120.8
C4A—C4—C7125.4 (6)C4B—C5B—C6B121.4 (7)
C5—C4—C788.5 (4)C4B—C5B—H5BA119.3
C3—C4—C789.2 (5)C6B—C5B—H5BA119.3
C6—C5—C289.9 (5)C5B—C6B—C1B122.0 (6)
C6—C5—C491.0 (6)C5B—C6B—H6BA119.0
C2—C5—C490.0 (5)C1B—C6B—H6BA119.0
C6—C5—H5A125.1C2C—C1C—C9C121.1 (5)
C2—C5—H5A125.1C2C—C1C—H1CA119.4
C4—C5—H5A125.1C9C—C1C—H1CA119.4
C5—C6—C790.2 (4)C1C—C2C—C3C119.0 (5)
C5—C6—C190.7 (5)C1C—C2C—C1122.3 (5)
C7—C6—C191.7 (5)C3C—C2C—C1118.7 (5)
C5—C6—H6A124.6C4C—C3C—C2C121.3 (6)
C7—C6—H6A124.6C4C—C3C—H3CA119.4
C1—C6—H6A124.6C2C—C3C—H3CA119.4
C6—C7—C889.2 (5)C3C—C4C—C10C120.8 (6)
C6—C7—C490.3 (5)C3C—C4C—H4CA119.6
C8—C7—C489.8 (5)C10C—C4C—H4CA119.6
C6—C7—H7A125.4C6C—C5C—C10C120.7 (6)
C8—C7—H7A125.4C6C—C5C—H5CA119.7
C4—C7—H7A125.4C10C—C5C—H5CA119.7
C3—C8—C790.5 (5)C5C—C6C—C7C120.4 (6)
C3—C8—C191.2 (5)C5C—C6C—H6CA119.8
C7—C8—C191.0 (5)C7C—C6C—H6CA119.8
C3—C8—H8A124.6C8C—C7C—C6C120.9 (6)
C7—C8—H8A124.6C8C—C7C—H7CA119.6
C1—C8—H8A124.6C6C—C7C—H7CA119.6
C6A—C1A—C2A116.1 (5)C7C—C8C—C9C120.4 (6)
C6A—C1A—C1B121.6 (5)C7C—C8C—H8CA119.8
C2A—C1A—C1B122.3 (5)C9C—C8C—H8CA119.8
C3A—C2A—C1A121.4 (6)C10C—C9C—C8C118.9 (5)
C3A—C2A—H2AA119.3C10C—C9C—C1C119.1 (5)
C1A—C2A—H2AA119.3C8C—C9C—C1C122.0 (5)
C2A—C3A—C4A122.2 (6)C4C—C10C—C9C118.8 (5)
C2A—C3A—H3AA118.9C4C—C10C—C5C122.5 (6)
C4A—C3A—H3AA118.9C9C—C10C—C5C118.7 (5)
C2C—C1—C2—C3134.8 (6)C2C—C1—C8—C7136.3 (6)
C6—C1—C2—C388.8 (5)C2—C1—C8—C789.8 (5)
C8—C1—C2—C30.7 (5)C6—C1—C8—C70.9 (5)
C2C—C1—C2—C5134.8 (6)C6A—C1A—C2A—C3A0.6 (9)
C6—C1—C2—C51.6 (5)C1B—C1A—C2A—C3A179.8 (7)
C8—C1—C2—C589.8 (5)C1A—C2A—C3A—C4A0.9 (11)
C5—C2—C3—C889.8 (5)C2A—C3A—C4A—C5A1.4 (11)
C1—C2—C3—C80.7 (5)C2A—C3A—C4A—C4175.5 (6)
C5—C2—C3—C40.7 (6)C5—C4—C4A—C3A91.9 (9)
C1—C2—C3—C491.2 (5)C3—C4—C4A—C3A29.1 (12)
C2—C3—C4—C4A135.2 (7)C7—C4—C4A—C3A149.9 (7)
C8—C3—C4—C4A135.5 (7)C5—C4—C4A—C5A84.8 (9)
C2—C3—C4—C50.7 (6)C3—C4—C4A—C5A154.2 (7)
C8—C3—C4—C588.5 (5)C7—C4—C4A—C5A33.4 (10)
C2—C3—C4—C789.2 (5)C3A—C4A—C5A—C6A1.8 (11)
C8—C3—C4—C70.0 (6)C4—C4A—C5A—C6A175.1 (7)
C3—C2—C5—C690.3 (6)C4A—C5A—C6A—C1A1.7 (11)
C1—C2—C5—C61.6 (5)C2A—C1A—C6A—C5A1.0 (10)
C3—C2—C5—C40.7 (6)C1B—C1A—C6A—C5A179.4 (7)
C1—C2—C5—C492.6 (6)C6A—C1A—C1B—C2B178.2 (7)
C4A—C4—C5—C6134.1 (6)C2A—C1A—C1B—C2B2.2 (10)
C3—C4—C5—C689.2 (5)C6A—C1A—C1B—C6B2.0 (10)
C7—C4—C5—C60.0 (5)C2A—C1A—C1B—C6B177.6 (7)
C4A—C4—C5—C2136.0 (6)C6B—C1B—C2B—C3B0.3 (11)
C3—C4—C5—C20.7 (6)C1A—C1B—C2B—C3B179.9 (7)
C7—C4—C5—C290.0 (5)C1B—C2B—C3B—C4B1.2 (12)
C2—C5—C6—C790.0 (5)C2B—C3B—C4B—C5B2.0 (12)
C4—C5—C6—C70.0 (5)C3B—C4B—C5B—C6B1.5 (12)
C2—C5—C6—C11.6 (5)C4B—C5B—C6B—C1B0.0 (12)
C4—C5—C6—C191.6 (5)C2B—C1B—C6B—C5B0.8 (10)
C2C—C1—C6—C5133.3 (7)C1A—C1B—C6B—C5B179.4 (7)
C2—C1—C6—C51.6 (5)C9C—C1C—C2C—C3C0.5 (10)
C8—C1—C6—C589.3 (5)C9C—C1C—C2C—C1178.0 (6)
C2C—C1—C6—C7136.4 (7)C2—C1—C2C—C1C139.1 (7)
C2—C1—C6—C788.6 (5)C6—C1—C2C—C1C19.0 (11)
C8—C1—C6—C70.9 (5)C8—C1—C2C—C1C102.6 (8)
C5—C6—C7—C889.8 (5)C2—C1—C2C—C3C38.4 (9)
C1—C6—C7—C80.9 (5)C6—C1—C2C—C3C158.4 (7)
C5—C6—C7—C40.0 (5)C8—C1—C2C—C3C79.9 (8)
C1—C6—C7—C490.7 (5)C1C—C2C—C3C—C4C1.0 (10)
C4A—C4—C7—C6134.3 (6)C1—C2C—C3C—C4C178.6 (6)
C5—C4—C7—C60.0 (5)C2C—C3C—C4C—C10C1.4 (10)
C3—C4—C7—C689.2 (5)C10C—C5C—C6C—C7C0.4 (11)
C4A—C4—C7—C8136.5 (6)C5C—C6C—C7C—C8C1.2 (12)
C5—C4—C7—C889.3 (5)C6C—C7C—C8C—C9C1.4 (11)
C3—C4—C7—C80.0 (6)C7C—C8C—C9C—C10C0.8 (9)
C2—C3—C8—C790.4 (5)C7C—C8C—C9C—C1C179.2 (7)
C4—C3—C8—C70.0 (6)C2C—C1C—C9C—C10C0.5 (9)
C2—C3—C8—C10.7 (5)C2C—C1C—C9C—C8C179.6 (6)
C4—C3—C8—C191.1 (5)C3C—C4C—C10C—C9C1.3 (9)
C6—C7—C8—C390.3 (6)C3C—C4C—C10C—C5C179.4 (6)
C4—C7—C8—C30.0 (6)C8C—C9C—C10C—C4C179.2 (6)
C6—C7—C8—C10.9 (5)C1C—C9C—C10C—C4C0.8 (8)
C4—C7—C8—C191.3 (5)C8C—C9C—C10C—C5C0.1 (8)
C2C—C1—C8—C3133.2 (6)C1C—C9C—C10C—C5C179.9 (6)
C2—C1—C8—C30.6 (5)C6C—C5C—C10C—C4C179.3 (6)
C6—C1—C8—C389.5 (5)C6C—C5C—C10C—C9C0.1 (9)

Experimental details

Crystal data
Chemical formulaC30H22
Mr382.48
Crystal system, space groupMonoclinic, P21
Temperature (K)294
a, b, c (Å)5.9788 (4), 7.579 (1), 22.044 (1)
β (°) 94.570 (8)
V3)995.71 (15)
Z2
Radiation typeCu Kα
µ (mm1)0.55
Crystal size (mm)0.52 × 0.16 × 0.02
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correctionIntegration
(Wuensch et al., 1965)
Tmin, Tmax0.847, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
2001, 2001, 1271
Rint0.038
(sin θ/λ)max1)0.605
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.168, 1.08
No. of reflections2001
No. of parameters273
No. of restraints7
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.19
Absolute structureSee text

Computer programs: XSCANS (Siemens, 1996), XSCANS, SHELXTL (Sheldrick, 1997), SHELXS97 (Sheldrick, 1990), SHELXTL.

Selected geometric parameters (Å, º) top
C1—C21.559 (9)C3—C41.559 (8)
C1—C61.560 (8)C4—C51.558 (9)
C1—C81.566 (9)C4—C71.573 (9)
C2—C31.535 (9)C5—C61.540 (10)
C2—C51.549 (10)C6—C71.542 (10)
C3—C81.546 (9)C7—C81.553 (9)
C2A—C1A—C1B—C2B2.2 (10)C6A—C1A—C1B—C6B2.0 (10)
 

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