organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1551

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

(Received 20 April 2012; accepted 23 April 2012; online 28 April 2012)

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)[Fun, H.-K., Quah, C. K. & Wu, D. (2012). Acta Cryst. E68, accepted [IS5123].]. For the preparation, see: Wu et al. (2012)[Wu, D., Wang, L., Xu, K., Song, J., Fun, H-K., Xu, J. & Zhang, Y. (2012). Chem. Commun. 48, 1168-1170.].

[Scheme 1]

Experimental

Crystal data
  • C22H16O4

  • Mr = 344.35

  • Orthorhombic, P b c a

  • a = 21.2454 (15) Å

  • b = 13.2363 (7) Å

  • c = 12.1954 (7) Å

  • V = 3429.5 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.27 × 0.22 × 0.08 mm

Data collection
  • Bruker SMART APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.993

  • 67362 measured reflections

  • 5014 independent reflections

  • 2961 reflections with I > 2σ(I)

  • Rint = 0.075

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.113

  • S = 0.99

  • 5014 reflections

  • 235 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

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)°.

Related literature top

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 top

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 column chromatography 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).

Refinement top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms.
1-Phenylethane-1,2-diyl 1,1'-biphenyl-2,2'-dicarboxylate top
Crystal data top
C22H16O4F(000) = 1440
Mr = 344.35Dx = 1.334 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 6139 reflections
a = 21.2454 (15) Åθ = 2.5–24.0°
b = 13.2363 (7) ŵ = 0.09 mm1
c = 12.1954 (7) ÅT = 296 K
V = 3429.5 (4) Å3Plate, colourless
Z = 80.27 × 0.22 × 0.08 mm
Data collection top
Bruker SMART APEXII DUO CCD
diffractometer
5014 independent reflections
Radiation source: fine-focus sealed tube2961 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
ϕ and ω scansθmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 2929
Tmin = 0.976, Tmax = 0.993k = 1818
67362 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-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 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C22H16O4V = 3429.5 (4) Å3
Mr = 344.35Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 21.2454 (15) ŵ = 0.09 mm1
b = 13.2363 (7) ÅT = 296 K
c = 12.1954 (7) Å0.27 × 0.22 × 0.08 mm
Data collection top
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 = 0.993Rint = 0.075
67362 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 0.99Δρmax = 0.16 e Å3
5014 reflectionsΔρmin = 0.16 e Å3
235 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.26894 (5)0.00729 (8)0.06424 (9)0.0525 (3)
O20.28774 (4)0.14794 (8)0.03621 (8)0.0431 (2)
O30.18085 (5)0.27892 (8)0.05404 (9)0.0517 (3)
O40.25786 (5)0.22593 (9)0.16930 (8)0.0494 (3)
C10.07994 (7)0.07069 (12)0.06878 (12)0.0481 (4)
H1A0.04150.07320.03230.058*
C20.08085 (7)0.06903 (14)0.18225 (13)0.0551 (4)
H2A0.04320.07080.22110.066*
C30.13733 (8)0.06473 (13)0.23800 (13)0.0525 (4)
H3A0.13780.06280.31420.063*
C40.19297 (7)0.06329 (12)0.18020 (12)0.0461 (4)
H4A0.23110.06110.21770.055*
C50.19263 (6)0.06515 (10)0.06611 (11)0.0375 (3)
C60.13535 (6)0.06867 (11)0.00836 (11)0.0382 (3)
C70.13142 (6)0.07071 (11)0.11413 (11)0.0397 (3)
C80.09627 (7)0.00380 (13)0.16669 (14)0.0492 (4)
H8A0.07570.05240.12500.059*
C90.09149 (8)0.00670 (14)0.27979 (15)0.0587 (5)
H9A0.06770.05690.31340.070*
C100.12184 (8)0.06460 (15)0.34267 (14)0.0602 (5)
H10A0.11850.06250.41870.072*
C110.15715 (7)0.13905 (14)0.29305 (12)0.0511 (4)
H11A0.17810.18660.33570.061*
C120.16148 (6)0.14330 (11)0.17924 (11)0.0404 (3)
C130.19893 (7)0.22471 (12)0.12604 (12)0.0417 (3)
C140.30724 (7)0.26949 (13)0.10300 (13)0.0508 (4)
H14A0.29000.32010.05390.061*
H14B0.33860.30140.14930.061*
C150.33672 (6)0.18389 (12)0.03764 (12)0.0433 (3)
H15A0.34920.12930.08740.052*
C160.25324 (6)0.06640 (11)0.00485 (12)0.0384 (3)
C170.39237 (6)0.21678 (12)0.02917 (12)0.0446 (3)
C180.45246 (7)0.18547 (15)0.00219 (14)0.0592 (4)
H18A0.45870.14390.05830.071*
C190.50365 (8)0.21590 (18)0.06533 (17)0.0737 (6)
H19A0.54410.19570.04600.088*
C200.49468 (9)0.27522 (16)0.15542 (18)0.0722 (6)
H20A0.52880.29360.19890.087*
C210.43562 (10)0.30752 (16)0.18154 (16)0.0706 (5)
H21A0.42980.34910.24220.085*
C220.38446 (8)0.27928 (14)0.11904 (14)0.0584 (4)
H22A0.34450.30240.13740.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0485 (6)0.0438 (6)0.0653 (7)0.0023 (5)0.0063 (5)0.0075 (5)
O20.0387 (5)0.0468 (6)0.0439 (5)0.0077 (4)0.0023 (4)0.0004 (5)
O30.0564 (6)0.0452 (6)0.0536 (6)0.0025 (5)0.0006 (5)0.0029 (5)
O40.0434 (5)0.0608 (7)0.0440 (6)0.0064 (5)0.0021 (4)0.0075 (5)
C10.0363 (7)0.0583 (10)0.0498 (9)0.0033 (7)0.0002 (6)0.0030 (8)
C20.0455 (8)0.0677 (12)0.0521 (10)0.0073 (8)0.0113 (7)0.0018 (8)
C30.0584 (9)0.0594 (10)0.0398 (8)0.0107 (8)0.0029 (7)0.0032 (7)
C40.0472 (8)0.0479 (9)0.0432 (8)0.0070 (7)0.0058 (6)0.0062 (7)
C50.0382 (7)0.0333 (7)0.0410 (7)0.0027 (6)0.0011 (6)0.0038 (6)
C60.0365 (7)0.0378 (7)0.0405 (7)0.0013 (6)0.0019 (6)0.0027 (6)
C70.0333 (6)0.0443 (8)0.0416 (7)0.0052 (6)0.0023 (6)0.0020 (6)
C80.0420 (7)0.0500 (9)0.0557 (9)0.0000 (7)0.0016 (7)0.0073 (8)
C90.0511 (9)0.0685 (12)0.0566 (10)0.0000 (9)0.0052 (8)0.0228 (9)
C100.0563 (9)0.0838 (14)0.0405 (8)0.0066 (10)0.0045 (7)0.0124 (9)
C110.0483 (8)0.0649 (11)0.0400 (8)0.0051 (8)0.0009 (7)0.0021 (8)
C120.0361 (6)0.0463 (8)0.0387 (7)0.0056 (6)0.0028 (6)0.0005 (6)
C130.0427 (7)0.0434 (8)0.0391 (7)0.0019 (6)0.0035 (6)0.0107 (7)
C140.0436 (8)0.0549 (10)0.0539 (9)0.0118 (7)0.0041 (7)0.0081 (8)
C150.0376 (7)0.0486 (8)0.0437 (8)0.0068 (6)0.0042 (6)0.0024 (7)
C160.0365 (6)0.0354 (7)0.0433 (7)0.0013 (6)0.0053 (6)0.0055 (6)
C170.0389 (7)0.0483 (9)0.0467 (8)0.0072 (7)0.0008 (6)0.0089 (7)
C180.0435 (8)0.0797 (13)0.0544 (10)0.0010 (8)0.0062 (7)0.0063 (9)
C190.0367 (8)0.1048 (17)0.0796 (14)0.0100 (10)0.0000 (9)0.0220 (13)
C200.0571 (10)0.0842 (14)0.0752 (13)0.0311 (10)0.0176 (10)0.0184 (11)
C210.0758 (12)0.0676 (13)0.0682 (12)0.0184 (10)0.0152 (10)0.0050 (10)
C220.0521 (9)0.0604 (11)0.0626 (11)0.0031 (8)0.0051 (8)0.0048 (9)
Geometric parameters (Å, º) top
O1—C161.1972 (17)C9—H9A0.9300
O2—C161.3596 (17)C10—C111.378 (2)
O2—C151.4562 (16)C10—H10A0.9300
O3—C131.1973 (17)C11—C121.392 (2)
O4—C131.3586 (17)C11—H11A0.9300
O4—C141.4446 (18)C12—C131.488 (2)
C1—C21.384 (2)C14—C151.520 (2)
C1—C61.3891 (19)C14—H14A0.9700
C1—H1A0.9300C14—H14B0.9700
C2—C31.380 (2)C15—C171.5003 (19)
C2—H2A0.9300C15—H15A0.9800
C3—C41.376 (2)C17—C181.382 (2)
C3—H3A0.9300C17—C221.383 (2)
C4—C51.3916 (19)C18—C191.392 (2)
C4—H4A0.9300C18—H18A0.9300
C5—C61.4068 (18)C19—C201.364 (3)
C5—C161.4888 (19)C19—H19A0.9300
C6—C71.4965 (19)C20—C211.363 (3)
C7—C81.393 (2)C20—H20A0.9300
C7—C121.400 (2)C21—C221.379 (2)
C8—C91.384 (2)C21—H21A0.9300
C8—H8A0.9300C22—H22A0.9300
C9—C101.376 (3)
C16—O2—C15118.08 (11)C7—C12—C13119.56 (12)
C13—O4—C14117.17 (12)O3—C13—O4124.98 (14)
C2—C1—C6121.21 (14)O3—C13—C12125.60 (13)
C2—C1—H1A119.4O4—C13—C12109.39 (13)
C6—C1—H1A119.4O4—C14—C15107.18 (13)
C3—C2—C1120.35 (14)O4—C14—H14A110.3
C3—C2—H2A119.8C15—C14—H14A110.3
C1—C2—H2A119.8O4—C14—H14B110.3
C4—C3—C2119.66 (14)C15—C14—H14B110.3
C4—C3—H3A120.2H14A—C14—H14B108.5
C2—C3—H3A120.2O2—C15—C17108.79 (11)
C3—C4—C5120.49 (14)O2—C15—C14105.86 (11)
C3—C4—H4A119.8C17—C15—C14113.15 (13)
C5—C4—H4A119.8O2—C15—H15A109.6
C4—C5—C6120.37 (13)C17—C15—H15A109.6
C4—C5—C16119.83 (12)C14—C15—H15A109.6
C6—C5—C16119.77 (12)O1—C16—O2124.52 (13)
C1—C6—C5117.92 (13)O1—C16—C5125.93 (13)
C1—C6—C7118.80 (12)O2—C16—C5109.50 (12)
C5—C6—C7123.27 (12)C18—C17—C22118.70 (15)
C8—C7—C12117.99 (13)C18—C17—C15120.77 (15)
C8—C7—C6118.44 (13)C22—C17—C15120.53 (14)
C12—C7—C6123.57 (13)C17—C18—C19120.21 (18)
C9—C8—C7121.17 (16)C17—C18—H18A119.9
C9—C8—H8A119.4C19—C18—H18A119.9
C7—C8—H8A119.4C20—C19—C18120.20 (18)
C10—C9—C8120.13 (16)C20—C19—H19A119.9
C10—C9—H9A119.9C18—C19—H19A119.9
C8—C9—H9A119.9C21—C20—C19119.83 (17)
C9—C10—C11120.04 (15)C21—C20—H20A120.1
C9—C10—H10A120.0C19—C20—H20A120.1
C11—C10—H10A120.0C20—C21—C22120.74 (19)
C10—C11—C12120.17 (16)C20—C21—H21A119.6
C10—C11—H11A119.9C22—C21—H21A119.6
C12—C11—H11A119.9C21—C22—C17120.28 (17)
C11—C12—C7120.49 (14)C21—C22—H22A119.9
C11—C12—C13119.94 (14)C17—C22—H22A119.9
C6—C1—C2—C30.4 (3)C11—C12—C13—O3129.03 (16)
C1—C2—C3—C40.8 (3)C7—C12—C13—O351.7 (2)
C2—C3—C4—C50.6 (3)C11—C12—C13—O453.03 (17)
C3—C4—C5—C60.1 (2)C7—C12—C13—O4126.21 (13)
C3—C4—C5—C16178.33 (15)C13—O4—C14—C1592.18 (15)
C2—C1—C6—C50.2 (2)C16—O2—C15—C17141.79 (12)
C2—C1—C6—C7179.94 (15)C16—O2—C15—C1496.32 (14)
C4—C5—C6—C10.3 (2)O4—C14—C15—O265.31 (15)
C16—C5—C6—C1177.94 (14)O4—C14—C15—C17175.64 (12)
C4—C5—C6—C7179.93 (14)C15—O2—C16—O118.96 (19)
C16—C5—C6—C71.8 (2)C15—O2—C16—C5158.71 (11)
C1—C6—C7—C856.42 (19)C4—C5—C16—O1124.59 (16)
C5—C6—C7—C8123.83 (15)C6—C5—C16—O157.1 (2)
C1—C6—C7—C12123.92 (16)C4—C5—C16—O257.78 (17)
C5—C6—C7—C1255.8 (2)C6—C5—C16—O2120.49 (14)
C12—C7—C8—C90.5 (2)O2—C15—C17—C18132.03 (15)
C6—C7—C8—C9179.19 (14)C14—C15—C17—C18110.62 (17)
C7—C8—C9—C100.2 (3)O2—C15—C17—C2248.06 (19)
C8—C9—C10—C110.1 (3)C14—C15—C17—C2269.29 (19)
C9—C10—C11—C121.0 (2)C22—C17—C18—C190.6 (3)
C10—C11—C12—C71.6 (2)C15—C17—C18—C19179.52 (16)
C10—C11—C12—C13179.13 (14)C17—C18—C19—C201.3 (3)
C8—C7—C12—C111.4 (2)C18—C19—C20—C212.2 (3)
C6—C7—C12—C11178.28 (13)C19—C20—C21—C221.3 (3)
C8—C7—C12—C13179.39 (13)C20—C21—C22—C170.6 (3)
C6—C7—C12—C131.0 (2)C18—C17—C22—C211.5 (3)
C14—O4—C13—O321.5 (2)C15—C17—C22—C21178.61 (16)
C14—O4—C13—C12156.50 (12)

Experimental details

Crystal data
Chemical formulaC22H16O4
Mr344.35
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)21.2454 (15), 13.2363 (7), 12.1954 (7)
V3)3429.5 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.27 × 0.22 × 0.08
Data collection
DiffractometerBruker SMART APEXII DUO CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.976, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
67362, 5014, 2961
Rint0.075
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.113, 0.99
No. of reflections5014
No. of parameters235
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.16

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

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

First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFun, H.-K., Quah, C. K. & Wu, D. (2012). Acta Cryst. E68, accepted [IS5123].  CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWu, D., Wang, L., Xu, K., Song, J., Fun, H-K., Xu, J. & Zhang, Y. (2012). Chem. Commun. 48, 1168–1170.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1551
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