Dimethyl biphenyl-4,4'-dicarboxyl-ate.

The asymmetric unit of the title compound, C(16)H(14)O(4), consists of one half-mol-ecule of an essentially planar biphenyl-dicarboxylic acid ester, with the complete molecule generated by an inversion centre. The maximum deviation from a least-squares plane through all non-H atoms occurs for the peripheric methyl groups and amounts to 0.124 (2) Å. The solid represents a typical mol-ecular crystal without classical hydrogen bonds. The shortest inter-molecular contacts do not differ significantly from the sum of the van der Waals radii of the atoms involved.

Related literature

For standard van der Waals radii, see: Bondi (1964 ▶). For related structures, see: Li & Brisse (1994 ▶); Marsh & Clemente (2007 ▶); Tashiro et al. (1990 ▶).

Experimental

Crystal data

C16H14O4

M = 270.27

Orthorhombic,

a = 7.1358 (9) Å

b = 5.9752 (8) Å

c = 29.709 (4) Å

V = 1266.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.11 × 0.06 × 0.01 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

14661 measured reflections

1585 independent reflections

1242 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.142

S = 1.08

1585 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023605/hg2528sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023605/hg2528Isup2.hkl

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

C16H14O4	F(000) = 568
Mr = 270.27	Dx = 1.417 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2384 reflections
a = 7.1358 (9) Å	θ = 2.7–27.9°
b = 5.9752 (8) Å	µ = 0.10 mm−1
c = 29.709 (4) Å	T = 100 K
V = 1266.7 (3) Å3	Plate, colourless
Z = 4	0.11 × 0.06 × 0.01 mm

Bruker SMART CCD area-detector diffractometer	1242 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
graphite	θmax = 28.4°, θmin = 2.7°
ω scans	h = −9→9
14661 measured reflections	k = −8→7
1585 independent reflections	l = −39→39

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.07P)2 + 0.4P] where P = (Fo2 + 2Fc2)/3
1585 reflections	(Δ/σ)max < 0.001
92 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.43822 (17)	0.51545 (19)	0.16205 (4)	0.0236 (3)
O2	0.55690 (18)	0.1972 (2)	0.19068 (4)	0.0299 (3)
C1	0.49919 (19)	0.0457 (2)	0.02340 (4)	0.0127 (3)
C2	0.42227 (19)	0.2566 (2)	0.03299 (5)	0.0152 (3)
H2	0.3706	0.3428	0.0092	0.018*
C3	0.41984 (19)	0.3421 (2)	0.07637 (5)	0.0155 (3)
H3	0.3675	0.4857	0.0819	0.019*
C4	0.49395 (19)	0.2179 (3)	0.11195 (5)	0.0153 (3)
C5	0.5698 (2)	0.0075 (2)	0.10315 (5)	0.0171 (3)
H5	0.6194	−0.0791	0.1272	0.021*
C6	0.5736 (2)	−0.0766 (2)	0.05963 (5)	0.0165 (3)
H6	0.6274	−0.2195	0.0542	0.020*
C7	0.4997 (2)	0.3039 (3)	0.15895 (5)	0.0178 (3)
C8	0.4498 (3)	0.6139 (3)	0.20658 (6)	0.0271 (4)
H8A	0.3676	0.5318	0.2272	0.041*
H8B	0.4104	0.7708	0.2052	0.041*
H8C	0.5793	0.6055	0.2174	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0335 (7)	0.0195 (6)	0.0177 (6)	0.0065 (5)	−0.0029 (5)	−0.0049 (4)
O2	0.0465 (8)	0.0260 (7)	0.0172 (6)	0.0084 (6)	−0.0047 (5)	0.0001 (5)
C1	0.0095 (6)	0.0129 (7)	0.0157 (7)	−0.0016 (5)	0.0015 (5)	0.0009 (5)
C2	0.0142 (7)	0.0144 (7)	0.0170 (7)	0.0016 (5)	−0.0017 (5)	0.0024 (5)
C3	0.0129 (7)	0.0133 (7)	0.0204 (8)	0.0013 (5)	−0.0006 (5)	−0.0008 (5)
C4	0.0142 (7)	0.0166 (7)	0.0152 (7)	−0.0012 (6)	0.0013 (5)	0.0003 (5)
C5	0.0170 (8)	0.0168 (7)	0.0174 (7)	0.0021 (6)	−0.0009 (6)	0.0023 (5)
C6	0.0172 (7)	0.0131 (7)	0.0193 (7)	0.0028 (5)	0.0009 (6)	0.0005 (5)
C7	0.0180 (8)	0.0181 (8)	0.0173 (7)	−0.0009 (6)	0.0007 (6)	0.0000 (5)
C8	0.0343 (10)	0.0261 (9)	0.0210 (8)	0.0033 (7)	−0.0019 (7)	−0.0092 (7)

O1—C7	1.3409 (19)	C3—H3	0.95
O1—C8	1.4502 (19)	C4—C5	1.394 (2)
O2—C7	1.2093 (18)	C4—C7	1.488 (2)
C1—C2	1.4035 (19)	C5—C6	1.387 (2)
C1—C6	1.4052 (19)	C5—H5	0.95
C1—C1i	1.494 (3)	C6—H6	0.95
C2—C3	1.386 (2)	C8—H8A	0.98
C2—H2	0.95	C8—H8B	0.98
C3—C4	1.395 (2)	C8—H8C	0.98
C7—O1—C8	115.23 (12)	C6—C5—H5	119.7
C2—C1—C6	117.32 (13)	C4—C5—H5	119.7
C2—C1—C1i	121.35 (15)	C5—C6—C1	121.21 (13)
C6—C1—C1i	121.33 (16)	C5—C6—H6	119.4
C3—C2—C1	121.64 (13)	C1—C6—H6	119.4
C3—C2—H2	119.2	O2—C7—O1	123.63 (14)
C1—C2—H2	119.2	O2—C7—C4	123.96 (14)
C2—C3—C4	120.23 (13)	O1—C7—C4	112.39 (13)
C2—C3—H3	119.9	O1—C8—H8A	109.5
C4—C3—H3	119.9	O1—C8—H8B	109.5
C5—C4—C3	118.99 (14)	H8A—C8—H8B	109.5
C5—C4—C7	118.47 (13)	O1—C8—H8C	109.5
C3—C4—C7	122.52 (13)	H8A—C8—H8C	109.5
C6—C5—C4	120.60 (14)	H8B—C8—H8C	109.5