1,1'-Bicyclo-propyl-1,1'-diyl 1,1'-biphenyl-2,2'-dicarboxyl-ate.

In the title compound, C(20)H(16)O(4), the two benzene rings form a dihedral angle of 45.70 (4)°. In the crystal, mol-ecules are linked via C-H⋯O inter-actions into layers lying parallel to the bc plane.

Related literature

For the background to this study, see the first paper in this series: Fun, Quah, Wu & Zhang (2012 ▶). For related structures in this series, see: Fun, Lim, Quah & Wu (2012 ▶); Fun, Quah & Wu (2012 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the preparation, see: Wu et al. (2012 ▶).

Experimental

Crystal data

C20H16O4

M = 320.33

Monoclinic,

a = 26.3197 (14) Å

b = 9.4184 (5) Å

c = 13.3606 (7) Å

β = 100.092 (1)°

V = 3260.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.43 × 0.34 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.962, T max = 0.985

12233 measured reflections

5234 independent reflections

3687 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.04

5234 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201851X/is5125sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201851X/is5125Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201851X/is5125Isup3.cml

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

C20H16O4	F(000) = 1344
Mr = 320.33	Dx = 1.305 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5289 reflections
a = 26.3197 (14) Å	θ = 2.7–31.1°
b = 9.4184 (5) Å	µ = 0.09 mm−1
c = 13.3606 (7) Å	T = 296 K
β = 100.092 (1)°	Block, colourless
V = 3260.7 (3) Å3	0.43 × 0.34 × 0.17 mm
Z = 8

Bruker SMART APEXII DUO CCD area-detector diffractometer	5234 independent reflections
Radiation source: fine-focus sealed tube	3687 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 31.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −38→30
Tmin = 0.962, Tmax = 0.985	k = −10→13
12233 measured reflections	l = −19→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.6692P] where P = (Fo2 + 2Fc2)/3
5234 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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	0.16306 (3)	0.77985 (9)	0.06344 (6)	0.0449 (2)
O2	0.14795 (3)	0.54239 (8)	0.06055 (6)	0.03836 (18)
O3	0.09630 (3)	0.53439 (9)	0.24353 (7)	0.0472 (2)
O4	0.17759 (3)	0.62505 (9)	0.26443 (6)	0.03936 (19)
C1	−0.00465 (5)	0.77534 (15)	0.06104 (11)	0.0523 (3)
H1A	−0.0238	0.8243	0.1021	0.063*
C2	−0.02987 (5)	0.70956 (16)	−0.02684 (12)	0.0591 (4)
H2A	−0.0656	0.7157	−0.0442	0.071*
C3	−0.00266 (5)	0.63585 (15)	−0.08813 (10)	0.0549 (4)
H3A	−0.0197	0.5930	−0.1473	0.066*
C4	0.05052 (5)	0.62568 (13)	−0.06123 (9)	0.0447 (3)
H4A	0.0691	0.5737	−0.1017	0.054*
C5	0.07625 (4)	0.69263 (11)	0.02585 (8)	0.0354 (2)
C6	0.04899 (4)	0.76921 (12)	0.08875 (9)	0.0390 (2)
C7	0.07330 (4)	0.84548 (12)	0.18338 (9)	0.0412 (3)
C8	0.05919 (5)	0.98669 (15)	0.19508 (13)	0.0598 (4)
H8A	0.0359	1.0299	0.1437	0.072*
C9	0.07889 (6)	1.06313 (17)	0.28054 (15)	0.0731 (5)
H9A	0.0687	1.1568	0.2864	0.088*
C10	0.11352 (6)	1.00248 (18)	0.35741 (14)	0.0687 (5)
H10A	0.1263	1.0542	0.4157	0.082*
C11	0.12910 (5)	0.86488 (16)	0.34756 (10)	0.0521 (3)
H11A	0.1533	0.8245	0.3987	0.063*
C12	0.10904 (4)	0.78468 (13)	0.26178 (9)	0.0387 (2)
C13	0.12509 (4)	0.63393 (12)	0.25576 (7)	0.0357 (2)
C14	0.19823 (4)	0.49827 (13)	0.22704 (9)	0.0429 (3)
C15	0.19826 (4)	0.50931 (12)	0.11551 (8)	0.0384 (2)
C16	0.13365 (4)	0.68165 (12)	0.05129 (7)	0.0343 (2)
C17	0.24439 (5)	0.55872 (15)	0.07486 (10)	0.0489 (3)
H17A	0.2754	0.5802	0.1233	0.059*
H17B	0.2387	0.6182	0.0147	0.059*
C18	0.22764 (5)	0.40633 (15)	0.06318 (11)	0.0538 (3)
H18A	0.2119	0.3740	−0.0040	0.065*
H18B	0.2485	0.3360	0.1046	0.065*
C19	0.19195 (7)	0.36209 (18)	0.27970 (13)	0.0696 (4)
H19A	0.1885	0.2759	0.2393	0.084*
H19B	0.1722	0.3634	0.3346	0.084*
C20	0.24300 (6)	0.4358 (2)	0.29662 (11)	0.0694 (5)
H20A	0.2542	0.4817	0.3617	0.083*
H20B	0.2705	0.3943	0.2665	0.083*

	U11	U22	U33	U12	U13	U23
O1	0.0411 (4)	0.0398 (5)	0.0524 (5)	−0.0053 (3)	0.0041 (3)	0.0041 (4)
O2	0.0387 (4)	0.0360 (4)	0.0382 (4)	0.0023 (3)	0.0007 (3)	−0.0012 (3)
O3	0.0456 (4)	0.0456 (5)	0.0504 (5)	−0.0062 (4)	0.0084 (4)	0.0037 (4)
O4	0.0337 (4)	0.0490 (5)	0.0351 (4)	0.0054 (3)	0.0052 (3)	−0.0027 (3)
C1	0.0362 (6)	0.0546 (8)	0.0642 (8)	0.0055 (5)	0.0043 (5)	0.0055 (6)
C2	0.0369 (6)	0.0623 (9)	0.0709 (9)	−0.0037 (6)	−0.0102 (6)	0.0134 (7)
C3	0.0519 (7)	0.0561 (8)	0.0486 (7)	−0.0126 (6)	−0.0135 (6)	0.0087 (6)
C4	0.0500 (6)	0.0437 (7)	0.0370 (5)	−0.0049 (5)	−0.0017 (5)	0.0032 (5)
C5	0.0360 (5)	0.0331 (5)	0.0351 (5)	−0.0022 (4)	0.0005 (4)	0.0064 (4)
C6	0.0351 (5)	0.0359 (6)	0.0442 (6)	0.0029 (4)	0.0020 (4)	0.0045 (5)
C7	0.0367 (5)	0.0373 (6)	0.0502 (6)	0.0015 (4)	0.0091 (5)	−0.0051 (5)
C8	0.0554 (7)	0.0439 (7)	0.0795 (10)	0.0075 (6)	0.0101 (7)	−0.0091 (7)
C9	0.0669 (9)	0.0481 (8)	0.1057 (13)	0.0041 (7)	0.0188 (9)	−0.0300 (9)
C10	0.0543 (8)	0.0691 (10)	0.0843 (11)	−0.0093 (7)	0.0165 (7)	−0.0430 (9)
C11	0.0368 (6)	0.0655 (9)	0.0539 (7)	−0.0037 (5)	0.0077 (5)	−0.0234 (6)
C12	0.0305 (5)	0.0437 (6)	0.0430 (6)	−0.0016 (4)	0.0099 (4)	−0.0089 (5)
C13	0.0352 (5)	0.0447 (6)	0.0273 (4)	0.0002 (4)	0.0059 (4)	0.0003 (4)
C14	0.0445 (6)	0.0479 (7)	0.0364 (5)	0.0152 (5)	0.0072 (4)	0.0055 (5)
C15	0.0379 (5)	0.0409 (6)	0.0353 (5)	0.0081 (4)	0.0036 (4)	−0.0031 (4)
C16	0.0380 (5)	0.0364 (6)	0.0280 (4)	0.0007 (4)	0.0046 (4)	0.0027 (4)
C17	0.0420 (6)	0.0606 (8)	0.0451 (6)	0.0037 (5)	0.0105 (5)	−0.0069 (6)
C18	0.0544 (7)	0.0559 (8)	0.0505 (7)	0.0153 (6)	0.0079 (5)	−0.0132 (6)
C19	0.0852 (11)	0.0595 (9)	0.0680 (10)	0.0263 (8)	0.0240 (8)	0.0266 (8)
C20	0.0645 (9)	0.0966 (12)	0.0456 (7)	0.0407 (9)	0.0053 (6)	0.0153 (8)

O1—C16	1.1986 (13)	C9—C10	1.373 (2)
O2—C16	1.3641 (13)	C9—H9A	0.9300
O2—C15	1.4314 (12)	C10—C11	1.373 (2)
O3—C13	1.1984 (13)	C10—H10A	0.9300
O4—C13	1.3688 (12)	C11—C12	1.3967 (16)
O4—C14	1.4372 (14)	C11—H11A	0.9300
C1—C2	1.389 (2)	C12—C13	1.4875 (16)
C1—C6	1.3966 (15)	C14—C19	1.486 (2)
C1—H1A	0.9300	C14—C20	1.4883 (16)
C2—C3	1.368 (2)	C14—C15	1.4939 (16)
C2—H2A	0.9300	C15—C18	1.4889 (17)
C3—C4	1.3859 (17)	C15—C17	1.4889 (17)
C3—H3A	0.9300	C17—C18	1.502 (2)
C4—C5	1.3906 (15)	C17—H17A	0.9700
C4—H4A	0.9300	C17—H17B	0.9700
C5—C6	1.3972 (17)	C18—H18A	0.9700
C5—C16	1.4930 (14)	C18—H18B	0.9700
C6—C7	1.4967 (16)	C19—C20	1.494 (3)
C7—C8	1.3970 (18)	C19—H19A	0.9700
C7—C12	1.4017 (16)	C19—H19B	0.9700
C8—C9	1.372 (2)	C20—H20A	0.9700
C8—H8A	0.9300	C20—H20B	0.9700
C16—O2—C15	118.13 (8)	O4—C13—C12	110.23 (9)
C13—O4—C14	117.31 (9)	O4—C14—C19	118.18 (11)
C2—C1—C6	121.11 (13)	O4—C14—C20	114.67 (11)
C2—C1—H1A	119.4	C19—C14—C20	60.30 (11)
C6—C1—H1A	119.4	O4—C14—C15	110.81 (9)
C3—C2—C1	120.63 (12)	C19—C14—C15	123.50 (12)
C3—C2—H2A	119.7	C20—C14—C15	120.79 (11)
C1—C2—H2A	119.7	O2—C15—C18	114.25 (9)
C2—C3—C4	119.39 (12)	O2—C15—C17	119.02 (10)
C2—C3—H3A	120.3	C18—C15—C17	60.56 (9)
C4—C3—H3A	120.3	O2—C15—C14	111.39 (9)
C3—C4—C5	120.48 (13)	C18—C15—C14	120.94 (10)
C3—C4—H4A	119.8	C17—C15—C14	121.91 (10)
C5—C4—H4A	119.8	O1—C16—O2	124.63 (10)
C4—C5—C6	120.75 (10)	O1—C16—C5	125.52 (10)
C4—C5—C16	118.95 (11)	O2—C16—C5	109.84 (9)
C6—C5—C16	120.30 (9)	C15—C17—C18	59.72 (9)
C1—C6—C5	117.62 (11)	C15—C17—H17A	117.8
C1—C6—C7	117.82 (11)	C18—C17—H17A	117.8
C5—C6—C7	124.57 (9)	C15—C17—H17B	117.8
C8—C7—C12	117.51 (11)	C18—C17—H17B	117.8
C8—C7—C6	117.96 (11)	H17A—C17—H17B	114.9
C12—C7—C6	124.52 (10)	C15—C18—C17	59.72 (8)
C9—C8—C7	121.57 (14)	C15—C18—H18A	117.8
C9—C8—H8A	119.2	C17—C18—H18A	117.8
C7—C8—H8A	119.2	C15—C18—H18B	117.8
C8—C9—C10	120.58 (14)	C17—C18—H18B	117.8
C8—C9—H9A	119.7	H18A—C18—H18B	114.9
C10—C9—H9A	119.7	C14—C19—C20	59.92 (10)
C11—C10—C9	119.44 (13)	C14—C19—H19A	117.8
C11—C10—H10A	120.3	C20—C19—H19A	117.8
C9—C10—H10A	120.3	C14—C19—H19B	117.8
C10—C11—C12	120.87 (13)	C20—C19—H19B	117.8
C10—C11—H11A	119.6	H19A—C19—H19B	114.9
C12—C11—H11A	119.6	C14—C20—C19	59.78 (9)
C11—C12—C7	120.00 (11)	C14—C20—H20A	117.8
C11—C12—C13	119.38 (11)	C19—C20—H20A	117.8
C7—C12—C13	120.61 (10)	C14—C20—H20B	117.8
O3—C13—O4	124.64 (11)	C19—C20—H20B	117.8
O3—C13—C12	125.13 (10)	H20A—C20—H20B	114.9
C6—C1—C2—C3	0.6 (2)	C7—C12—C13—O4	123.65 (11)
C1—C2—C3—C4	0.8 (2)	C13—O4—C14—C19	−66.02 (14)
C2—C3—C4—C5	−1.62 (19)	C13—O4—C14—C20	−134.16 (12)
C3—C4—C5—C6	1.13 (17)	C13—O4—C14—C15	84.84 (12)
C3—C4—C5—C16	−178.81 (11)	C16—O2—C15—C18	−132.94 (11)
C2—C1—C6—C5	−1.04 (19)	C16—O2—C15—C17	−64.44 (13)
C2—C1—C6—C7	178.72 (12)	C16—O2—C15—C14	85.60 (12)
C4—C5—C6—C1	0.20 (17)	O4—C14—C15—O2	−54.61 (13)
C16—C5—C6—C1	−179.86 (11)	C19—C14—C15—O2	94.42 (14)
C4—C5—C6—C7	−179.54 (11)	C20—C14—C15—O2	167.13 (12)
C16—C5—C6—C7	0.40 (17)	O4—C14—C15—C18	166.88 (11)
C1—C6—C7—C8	−49.77 (17)	C19—C14—C15—C18	−44.10 (18)
C5—C6—C7—C8	129.97 (13)	C20—C14—C15—C18	28.61 (19)
C1—C6—C7—C12	129.69 (13)	O4—C14—C15—C17	94.44 (13)
C5—C6—C7—C12	−50.56 (18)	C19—C14—C15—C17	−116.54 (15)
C12—C7—C8—C9	−0.9 (2)	C20—C14—C15—C17	−43.82 (18)
C6—C7—C8—C9	178.62 (14)	C15—O2—C16—O1	18.83 (16)
C7—C8—C9—C10	0.3 (3)	C15—O2—C16—C5	−160.13 (9)
C8—C9—C10—C11	1.1 (3)	C4—C5—C16—O1	123.22 (13)
C9—C10—C11—C12	−1.9 (2)	C6—C5—C16—O1	−56.72 (16)
C10—C11—C12—C7	1.3 (2)	C4—C5—C16—O2	−57.83 (13)
C10—C11—C12—C13	−177.34 (13)	C6—C5—C16—O2	122.23 (11)
C8—C7—C12—C11	0.07 (18)	O2—C15—C17—C18	−103.08 (11)
C6—C7—C12—C11	−179.39 (11)	C14—C15—C17—C18	110.12 (12)
C8—C7—C12—C13	178.70 (12)	O2—C15—C18—C17	110.90 (11)
C6—C7—C12—C13	−0.76 (18)	C14—C15—C18—C17	−111.67 (13)
C14—O4—C13—O3	19.37 (15)	O4—C14—C19—C20	−103.86 (13)
C14—O4—C13—C12	−159.59 (9)	C15—C14—C19—C20	109.22 (14)
C11—C12—C13—O3	123.34 (13)	O4—C14—C20—C19	109.65 (13)
C7—C12—C13—O3	−55.30 (16)	C15—C14—C20—C19	−113.56 (15)
C11—C12—C13—O4	−57.71 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O3i	0.93	2.50	3.3410 (16)	151
C4—H4A···O3ii	0.93	2.52	3.4104 (15)	161
C10—H10A···O1iii	0.93	2.57	3.496 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O3i	0.93	2.50	3.3410 (16)	151
C4—H4A⋯O3ii	0.93	2.52	3.4104 (15)	161
C10—H10A⋯O1iii	0.93	2.57	3.496 (2)	174

Symmetry codes: (i) ; (ii) ; (iii) .