organic compounds
1-Phenylethane-1,2-diyl 1,1′-biphenyl-2,2′-dicarboxylate
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, People's Republic of China
*Correspondence e-mail: hkfun@usm.my
In the title compound, C22H16O4, the 7-phenyl ring is inclined at dihedral angles of 36.73 (9) and 69.37 (9)° with respect to the biphenyl benzene rings. The two benzene rings of the biphenyl unit form a dihedral angle of 55.99 (8)°. There are no significant hydrogen bonds observed in the crystal of this compound.
Related literature
For a related structure, references to other similar structures and chemical and biological background, see: Fun et al. (2012). For the preparation, see: Wu et al. (2012).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812018065/hb6748sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812018065/hb6748Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812018065/hb6748Isup3.cml
The title compound was the major diastereoisomer of the photoreaction products of 9,10-phenanthrenedione with styrene via a photocycloaddition-photooxidation sequence. The compound was purified by flash
with ethyl acetate/petroleum ether (1:9) as eluents. Colourless plates of the title compound was obtained from slow evaporation of an acetone and petroleum ether solution (1:10).All H atoms were positioned geometrically and refined using a riding model with C–H = 0.93-0.98 Å and Uiso(H) = 1.2 Ueq(C).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms. |
C22H16O4 | F(000) = 1440 |
Mr = 344.35 | Dx = 1.334 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 6139 reflections |
a = 21.2454 (15) Å | θ = 2.5–24.0° |
b = 13.2363 (7) Å | µ = 0.09 mm−1 |
c = 12.1954 (7) Å | T = 296 K |
V = 3429.5 (4) Å3 | Plate, colourless |
Z = 8 | 0.27 × 0.22 × 0.08 mm |
Bruker SMART APEXII DUO CCD diffractometer | 5014 independent reflections |
Radiation source: fine-focus sealed tube | 2961 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
ϕ and ω scans | θmax = 30.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −29→29 |
Tmin = 0.976, Tmax = 0.993 | k = −18→18 |
67362 measured reflections | l = −17→17 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0382P)2 + 0.8815P] where P = (Fo2 + 2Fc2)/3 |
5014 reflections | (Δ/σ)max = 0.001 |
235 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C22H16O4 | V = 3429.5 (4) Å3 |
Mr = 344.35 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 21.2454 (15) Å | µ = 0.09 mm−1 |
b = 13.2363 (7) Å | T = 296 K |
c = 12.1954 (7) Å | 0.27 × 0.22 × 0.08 mm |
Bruker SMART APEXII DUO CCD diffractometer | 5014 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2961 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.993 | Rint = 0.075 |
67362 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.16 e Å−3 |
5014 reflections | Δρmin = −0.16 e Å−3 |
235 parameters |
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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.26894 (5) | 0.00729 (8) | −0.06424 (9) | 0.0525 (3) | |
O2 | 0.28774 (4) | 0.14794 (8) | 0.03621 (8) | 0.0431 (2) | |
O3 | 0.18085 (5) | 0.27892 (8) | −0.05404 (9) | 0.0517 (3) | |
O4 | 0.25786 (5) | 0.22593 (9) | −0.16930 (8) | 0.0494 (3) | |
C1 | 0.07994 (7) | 0.07069 (12) | 0.06878 (12) | 0.0481 (4) | |
H1A | 0.0415 | 0.0732 | 0.0323 | 0.058* | |
C2 | 0.08085 (7) | 0.06903 (14) | 0.18225 (13) | 0.0551 (4) | |
H2A | 0.0432 | 0.0708 | 0.2211 | 0.066* | |
C3 | 0.13733 (8) | 0.06473 (13) | 0.23800 (13) | 0.0525 (4) | |
H3A | 0.1378 | 0.0628 | 0.3142 | 0.063* | |
C4 | 0.19297 (7) | 0.06329 (12) | 0.18020 (12) | 0.0461 (4) | |
H4A | 0.2311 | 0.0611 | 0.2177 | 0.055* | |
C5 | 0.19263 (6) | 0.06515 (10) | 0.06611 (11) | 0.0375 (3) | |
C6 | 0.13535 (6) | 0.06867 (11) | 0.00836 (11) | 0.0382 (3) | |
C7 | 0.13142 (6) | 0.07071 (11) | −0.11413 (11) | 0.0397 (3) | |
C8 | 0.09627 (7) | −0.00380 (13) | −0.16669 (14) | 0.0492 (4) | |
H8A | 0.0757 | −0.0524 | −0.1250 | 0.059* | |
C9 | 0.09149 (8) | −0.00670 (14) | −0.27979 (15) | 0.0587 (5) | |
H9A | 0.0677 | −0.0569 | −0.3134 | 0.070* | |
C10 | 0.12184 (8) | 0.06460 (15) | −0.34267 (14) | 0.0602 (5) | |
H10A | 0.1185 | 0.0625 | −0.4187 | 0.072* | |
C11 | 0.15715 (7) | 0.13905 (14) | −0.29305 (12) | 0.0511 (4) | |
H11A | 0.1781 | 0.1866 | −0.3357 | 0.061* | |
C12 | 0.16148 (6) | 0.14330 (11) | −0.17924 (11) | 0.0404 (3) | |
C13 | 0.19893 (7) | 0.22471 (12) | −0.12604 (12) | 0.0417 (3) | |
C14 | 0.30724 (7) | 0.26949 (13) | −0.10300 (13) | 0.0508 (4) | |
H14A | 0.2900 | 0.3201 | −0.0539 | 0.061* | |
H14B | 0.3386 | 0.3014 | −0.1493 | 0.061* | |
C15 | 0.33672 (6) | 0.18389 (12) | −0.03764 (12) | 0.0433 (3) | |
H15A | 0.3492 | 0.1293 | −0.0874 | 0.052* | |
C16 | 0.25324 (6) | 0.06640 (11) | 0.00485 (12) | 0.0384 (3) | |
C17 | 0.39237 (6) | 0.21678 (12) | 0.02917 (12) | 0.0446 (3) | |
C18 | 0.45246 (7) | 0.18547 (15) | 0.00219 (14) | 0.0592 (4) | |
H18A | 0.4587 | 0.1439 | −0.0583 | 0.071* | |
C19 | 0.50365 (8) | 0.21590 (18) | 0.06533 (17) | 0.0737 (6) | |
H19A | 0.5441 | 0.1957 | 0.0460 | 0.088* | |
C20 | 0.49468 (9) | 0.27522 (16) | 0.15542 (18) | 0.0722 (6) | |
H20A | 0.5288 | 0.2936 | 0.1989 | 0.087* | |
C21 | 0.43562 (10) | 0.30752 (16) | 0.18154 (16) | 0.0706 (5) | |
H21A | 0.4298 | 0.3491 | 0.2422 | 0.085* | |
C22 | 0.38446 (8) | 0.27928 (14) | 0.11904 (14) | 0.0584 (4) | |
H22A | 0.3445 | 0.3024 | 0.1374 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0485 (6) | 0.0438 (6) | 0.0653 (7) | 0.0023 (5) | 0.0063 (5) | −0.0075 (5) |
O2 | 0.0387 (5) | 0.0468 (6) | 0.0439 (5) | −0.0077 (4) | 0.0023 (4) | 0.0004 (5) |
O3 | 0.0564 (6) | 0.0452 (6) | 0.0536 (6) | 0.0025 (5) | −0.0006 (5) | −0.0029 (5) |
O4 | 0.0434 (5) | 0.0608 (7) | 0.0440 (6) | −0.0064 (5) | −0.0021 (4) | 0.0075 (5) |
C1 | 0.0363 (7) | 0.0583 (10) | 0.0498 (9) | −0.0033 (7) | −0.0002 (6) | 0.0030 (8) |
C2 | 0.0455 (8) | 0.0677 (12) | 0.0521 (10) | −0.0073 (8) | 0.0113 (7) | 0.0018 (8) |
C3 | 0.0584 (9) | 0.0594 (10) | 0.0398 (8) | −0.0107 (8) | 0.0029 (7) | 0.0032 (7) |
C4 | 0.0472 (8) | 0.0479 (9) | 0.0432 (8) | −0.0070 (7) | −0.0058 (6) | 0.0062 (7) |
C5 | 0.0382 (7) | 0.0333 (7) | 0.0410 (7) | −0.0027 (6) | −0.0011 (6) | 0.0038 (6) |
C6 | 0.0365 (7) | 0.0378 (7) | 0.0405 (7) | −0.0013 (6) | −0.0019 (6) | 0.0027 (6) |
C7 | 0.0333 (6) | 0.0443 (8) | 0.0416 (7) | 0.0052 (6) | −0.0023 (6) | −0.0020 (6) |
C8 | 0.0420 (7) | 0.0500 (9) | 0.0557 (9) | 0.0000 (7) | −0.0016 (7) | −0.0073 (8) |
C9 | 0.0511 (9) | 0.0685 (12) | 0.0566 (10) | 0.0000 (9) | −0.0052 (8) | −0.0228 (9) |
C10 | 0.0563 (9) | 0.0838 (14) | 0.0405 (8) | 0.0066 (10) | −0.0045 (7) | −0.0124 (9) |
C11 | 0.0483 (8) | 0.0649 (11) | 0.0400 (8) | 0.0051 (8) | −0.0009 (7) | 0.0021 (8) |
C12 | 0.0361 (6) | 0.0463 (8) | 0.0387 (7) | 0.0056 (6) | −0.0028 (6) | 0.0005 (6) |
C13 | 0.0427 (7) | 0.0434 (8) | 0.0391 (7) | 0.0019 (6) | −0.0035 (6) | 0.0107 (7) |
C14 | 0.0436 (8) | 0.0549 (10) | 0.0539 (9) | −0.0118 (7) | −0.0041 (7) | 0.0081 (8) |
C15 | 0.0376 (7) | 0.0486 (8) | 0.0437 (8) | −0.0068 (6) | 0.0042 (6) | 0.0024 (7) |
C16 | 0.0365 (6) | 0.0354 (7) | 0.0433 (7) | 0.0013 (6) | −0.0053 (6) | 0.0055 (6) |
C17 | 0.0389 (7) | 0.0483 (9) | 0.0467 (8) | −0.0072 (7) | 0.0008 (6) | 0.0089 (7) |
C18 | 0.0435 (8) | 0.0797 (13) | 0.0544 (10) | −0.0010 (8) | 0.0062 (7) | 0.0063 (9) |
C19 | 0.0367 (8) | 0.1048 (17) | 0.0796 (14) | −0.0100 (10) | 0.0000 (9) | 0.0220 (13) |
C20 | 0.0571 (10) | 0.0842 (14) | 0.0752 (13) | −0.0311 (10) | −0.0176 (10) | 0.0184 (11) |
C21 | 0.0758 (12) | 0.0676 (13) | 0.0682 (12) | −0.0184 (10) | −0.0152 (10) | −0.0050 (10) |
C22 | 0.0521 (9) | 0.0604 (11) | 0.0626 (11) | −0.0031 (8) | −0.0051 (8) | −0.0048 (9) |
O1—C16 | 1.1972 (17) | C9—H9A | 0.9300 |
O2—C16 | 1.3596 (17) | C10—C11 | 1.378 (2) |
O2—C15 | 1.4562 (16) | C10—H10A | 0.9300 |
O3—C13 | 1.1973 (17) | C11—C12 | 1.392 (2) |
O4—C13 | 1.3586 (17) | C11—H11A | 0.9300 |
O4—C14 | 1.4446 (18) | C12—C13 | 1.488 (2) |
C1—C2 | 1.384 (2) | C14—C15 | 1.520 (2) |
C1—C6 | 1.3891 (19) | C14—H14A | 0.9700 |
C1—H1A | 0.9300 | C14—H14B | 0.9700 |
C2—C3 | 1.380 (2) | C15—C17 | 1.5003 (19) |
C2—H2A | 0.9300 | C15—H15A | 0.9800 |
C3—C4 | 1.376 (2) | C17—C18 | 1.382 (2) |
C3—H3A | 0.9300 | C17—C22 | 1.383 (2) |
C4—C5 | 1.3916 (19) | C18—C19 | 1.392 (2) |
C4—H4A | 0.9300 | C18—H18A | 0.9300 |
C5—C6 | 1.4068 (18) | C19—C20 | 1.364 (3) |
C5—C16 | 1.4888 (19) | C19—H19A | 0.9300 |
C6—C7 | 1.4965 (19) | C20—C21 | 1.363 (3) |
C7—C8 | 1.393 (2) | C20—H20A | 0.9300 |
C7—C12 | 1.400 (2) | C21—C22 | 1.379 (2) |
C8—C9 | 1.384 (2) | C21—H21A | 0.9300 |
C8—H8A | 0.9300 | C22—H22A | 0.9300 |
C9—C10 | 1.376 (3) | ||
C16—O2—C15 | 118.08 (11) | C7—C12—C13 | 119.56 (12) |
C13—O4—C14 | 117.17 (12) | O3—C13—O4 | 124.98 (14) |
C2—C1—C6 | 121.21 (14) | O3—C13—C12 | 125.60 (13) |
C2—C1—H1A | 119.4 | O4—C13—C12 | 109.39 (13) |
C6—C1—H1A | 119.4 | O4—C14—C15 | 107.18 (13) |
C3—C2—C1 | 120.35 (14) | O4—C14—H14A | 110.3 |
C3—C2—H2A | 119.8 | C15—C14—H14A | 110.3 |
C1—C2—H2A | 119.8 | O4—C14—H14B | 110.3 |
C4—C3—C2 | 119.66 (14) | C15—C14—H14B | 110.3 |
C4—C3—H3A | 120.2 | H14A—C14—H14B | 108.5 |
C2—C3—H3A | 120.2 | O2—C15—C17 | 108.79 (11) |
C3—C4—C5 | 120.49 (14) | O2—C15—C14 | 105.86 (11) |
C3—C4—H4A | 119.8 | C17—C15—C14 | 113.15 (13) |
C5—C4—H4A | 119.8 | O2—C15—H15A | 109.6 |
C4—C5—C6 | 120.37 (13) | C17—C15—H15A | 109.6 |
C4—C5—C16 | 119.83 (12) | C14—C15—H15A | 109.6 |
C6—C5—C16 | 119.77 (12) | O1—C16—O2 | 124.52 (13) |
C1—C6—C5 | 117.92 (13) | O1—C16—C5 | 125.93 (13) |
C1—C6—C7 | 118.80 (12) | O2—C16—C5 | 109.50 (12) |
C5—C6—C7 | 123.27 (12) | C18—C17—C22 | 118.70 (15) |
C8—C7—C12 | 117.99 (13) | C18—C17—C15 | 120.77 (15) |
C8—C7—C6 | 118.44 (13) | C22—C17—C15 | 120.53 (14) |
C12—C7—C6 | 123.57 (13) | C17—C18—C19 | 120.21 (18) |
C9—C8—C7 | 121.17 (16) | C17—C18—H18A | 119.9 |
C9—C8—H8A | 119.4 | C19—C18—H18A | 119.9 |
C7—C8—H8A | 119.4 | C20—C19—C18 | 120.20 (18) |
C10—C9—C8 | 120.13 (16) | C20—C19—H19A | 119.9 |
C10—C9—H9A | 119.9 | C18—C19—H19A | 119.9 |
C8—C9—H9A | 119.9 | C21—C20—C19 | 119.83 (17) |
C9—C10—C11 | 120.04 (15) | C21—C20—H20A | 120.1 |
C9—C10—H10A | 120.0 | C19—C20—H20A | 120.1 |
C11—C10—H10A | 120.0 | C20—C21—C22 | 120.74 (19) |
C10—C11—C12 | 120.17 (16) | C20—C21—H21A | 119.6 |
C10—C11—H11A | 119.9 | C22—C21—H21A | 119.6 |
C12—C11—H11A | 119.9 | C21—C22—C17 | 120.28 (17) |
C11—C12—C7 | 120.49 (14) | C21—C22—H22A | 119.9 |
C11—C12—C13 | 119.94 (14) | C17—C22—H22A | 119.9 |
C6—C1—C2—C3 | −0.4 (3) | C11—C12—C13—O3 | 129.03 (16) |
C1—C2—C3—C4 | 0.8 (3) | C7—C12—C13—O3 | −51.7 (2) |
C2—C3—C4—C5 | −0.6 (3) | C11—C12—C13—O4 | −53.03 (17) |
C3—C4—C5—C6 | 0.1 (2) | C7—C12—C13—O4 | 126.21 (13) |
C3—C4—C5—C16 | 178.33 (15) | C13—O4—C14—C15 | 92.18 (15) |
C2—C1—C6—C5 | −0.2 (2) | C16—O2—C15—C17 | −141.79 (12) |
C2—C1—C6—C7 | −179.94 (15) | C16—O2—C15—C14 | 96.32 (14) |
C4—C5—C6—C1 | 0.3 (2) | O4—C14—C15—O2 | −65.31 (15) |
C16—C5—C6—C1 | −177.94 (14) | O4—C14—C15—C17 | 175.64 (12) |
C4—C5—C6—C7 | −179.93 (14) | C15—O2—C16—O1 | 18.96 (19) |
C16—C5—C6—C7 | 1.8 (2) | C15—O2—C16—C5 | −158.71 (11) |
C1—C6—C7—C8 | −56.42 (19) | C4—C5—C16—O1 | 124.59 (16) |
C5—C6—C7—C8 | 123.83 (15) | C6—C5—C16—O1 | −57.1 (2) |
C1—C6—C7—C12 | 123.92 (16) | C4—C5—C16—O2 | −57.78 (17) |
C5—C6—C7—C12 | −55.8 (2) | C6—C5—C16—O2 | 120.49 (14) |
C12—C7—C8—C9 | 0.5 (2) | O2—C15—C17—C18 | 132.03 (15) |
C6—C7—C8—C9 | −179.19 (14) | C14—C15—C17—C18 | −110.62 (17) |
C7—C8—C9—C10 | 0.2 (3) | O2—C15—C17—C22 | −48.06 (19) |
C8—C9—C10—C11 | 0.1 (3) | C14—C15—C17—C22 | 69.29 (19) |
C9—C10—C11—C12 | −1.0 (2) | C22—C17—C18—C19 | 0.6 (3) |
C10—C11—C12—C7 | 1.6 (2) | C15—C17—C18—C19 | −179.52 (16) |
C10—C11—C12—C13 | −179.13 (14) | C17—C18—C19—C20 | 1.3 (3) |
C8—C7—C12—C11 | −1.4 (2) | C18—C19—C20—C21 | −2.2 (3) |
C6—C7—C12—C11 | 178.28 (13) | C19—C20—C21—C22 | 1.3 (3) |
C8—C7—C12—C13 | 179.39 (13) | C20—C21—C22—C17 | 0.6 (3) |
C6—C7—C12—C13 | −1.0 (2) | C18—C17—C22—C21 | −1.5 (3) |
C14—O4—C13—O3 | 21.5 (2) | C15—C17—C22—C21 | 178.61 (16) |
C14—O4—C13—C12 | −156.50 (12) |
Experimental details
Crystal data | |
Chemical formula | C22H16O4 |
Mr | 344.35 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 296 |
a, b, c (Å) | 21.2454 (15), 13.2363 (7), 12.1954 (7) |
V (Å3) | 3429.5 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.27 × 0.22 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEXII DUO CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.976, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 67362, 5014, 2961 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.113, 0.99 |
No. of reflections | 5014 |
No. of parameters | 235 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.16 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Acknowledgements
HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). Financial support from the National Natural Science Foundation of China (20972067) is acknowledged.
References
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Quah, C. K. & Wu, D. (2012). Acta Cryst. E68, accepted [IS5123]. CrossRef IUCr Journals Google Scholar
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As part of our ongoing synthetic and structural studies of bis-lactones containing a biaryl motif (Wu et al., 2012; Fun et al. 2012), we now report the structure of the title compound, (I).
In the title compound, Fig. 1, the terminal benzene ring (C17-C22) inclines at dihedral angles of 36.73 (9) and 69.37 (9)° with the other two benzene rings (C1-C6 and C7-C12), respectively. The two benzene rings form a dihedral angle of 55.99 (8)°.