3,3'-Dibenzyl-3,3'-dihydr­oxy-[2,2'-bi-1H-indene]-1,1'-dione

The title compound, C₃₂H₂₄O₄, was synthesized by the reaction of benzyl­magnesium bromide with 2,2'-biindanyl­idene-1,1',3,3'-tetra­one. The mol­ecule lies across a crystallographic inversion centre. The cyclo­pentenone ring adopts a flattened envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.043
• wR factor = 0.121
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

3,3'-Dibenzyl-3,3'-dihydroxy-[2,2'-bi-1H-indene]-1,1'-dione

Crystal data

C32H24O4	F(000) = 992
Mr = 472.51	Dx = 1.299 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2620 reflections
a = 15.576 (6) Å	θ = 2.6–21.4°
b = 9.611 (4) Å	µ = 0.09 mm^−1
c = 16.139 (6) Å	T = 294 K
V = 2416.1 (17) Å^3	Block, yellow
Z = 4	0.22 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2462 independent reflections
Radiation source: fine-focus sealed tube	1482 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→16
Tmin = 0.979, Tmax = 0.989	k = −9→11
12722 measured reflections	l = −20→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0521P)^2 + 0.4227P] where P = (Fo^2 + 2Fc^2)/3
2462 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

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. 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.65842 (8)	0.57513 (15)	0.45300 (9)	0.0652 (4)
O2	0.38464 (8)	0.69523 (17)	0.55169 (9)	0.0574 (4)
H2	0.3606 (17)	0.605 (3)	0.5552 (17)	0.109 (10)*
C1	0.59950 (11)	0.6272 (2)	0.49314 (11)	0.0456 (5)
C2	0.51514 (10)	0.56101 (18)	0.51526 (10)	0.0401 (4)
C3	0.46932 (10)	0.66008 (18)	0.57587 (11)	0.0409 (4)
C4	0.52364 (11)	0.78932 (18)	0.57118 (11)	0.0431 (5)
C5	0.50771 (14)	0.9187 (2)	0.60669 (11)	0.0552 (5)
H5	0.4568	0.9355	0.6350	0.066*
C6	0.56912 (15)	1.0220 (2)	0.59903 (12)	0.0616 (6)
H6	0.5596	1.1082	0.6235	0.074*
C7	0.64517 (15)	0.9990 (2)	0.55510 (13)	0.0671 (6)
H7	0.6850	1.0705	0.5496	0.080*
C8	0.66163 (13)	0.8702 (2)	0.51966 (12)	0.0569 (5)
H8	0.7126	0.8530	0.4915	0.068*
C9	0.59926 (11)	0.7679 (2)	0.52776 (11)	0.0451 (5)
C10	0.46946 (12)	0.6018 (2)	0.66545 (11)	0.0483 (5)
H10A	0.4412	0.6684	0.7014	0.058*
H10B	0.4358	0.5168	0.6664	0.058*
C11	0.55721 (12)	0.5708 (2)	0.70053 (11)	0.0478 (5)
C12	0.59917 (14)	0.4470 (2)	0.68168 (12)	0.0597 (6)
H12	0.5727	0.3826	0.6471	0.072*
C13	0.67921 (17)	0.4186 (3)	0.71337 (15)	0.0814 (8)
H13	0.7069	0.3361	0.6995	0.098*
C14	0.71836 (18)	0.5122 (4)	0.76569 (17)	0.0957 (9)
H14	0.7721	0.4922	0.7877	0.115*
C15	0.67810 (19)	0.6358 (3)	0.78554 (15)	0.0842 (8)
H15	0.7045	0.6989	0.8210	0.101*
C16	0.59848 (15)	0.6649 (2)	0.75245 (12)	0.0632 (6)
H16	0.5719	0.7489	0.7651	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0415 (8)	0.0691 (10)	0.0850 (10)	−0.0017 (7)	0.0180 (7)	−0.0194 (8)
O2	0.0396 (8)	0.0598 (10)	0.0729 (10)	0.0129 (7)	−0.0040 (6)	−0.0072 (8)
C1	0.0374 (11)	0.0557 (12)	0.0437 (10)	0.0003 (9)	0.0007 (8)	−0.0007 (9)
C2	0.0348 (10)	0.0469 (11)	0.0387 (9)	0.0038 (8)	−0.0005 (7)	0.0001 (8)
C3	0.0351 (10)	0.0447 (11)	0.0428 (10)	0.0040 (8)	−0.0002 (8)	−0.0026 (8)
C4	0.0494 (11)	0.0438 (11)	0.0362 (9)	0.0053 (9)	−0.0043 (8)	0.0015 (8)
C5	0.0681 (13)	0.0489 (13)	0.0485 (11)	0.0083 (11)	0.0019 (10)	−0.0024 (9)
C6	0.0827 (16)	0.0405 (12)	0.0617 (14)	−0.0018 (12)	0.0003 (12)	−0.0017 (10)
C7	0.0791 (16)	0.0539 (14)	0.0682 (15)	−0.0170 (12)	−0.0030 (12)	0.0040 (11)
C8	0.0531 (12)	0.0594 (14)	0.0581 (12)	−0.0124 (11)	0.0020 (9)	−0.0008 (10)
C9	0.0453 (11)	0.0480 (11)	0.0420 (10)	−0.0025 (9)	−0.0041 (8)	0.0011 (8)
C10	0.0502 (11)	0.0498 (11)	0.0448 (10)	0.0004 (9)	0.0087 (9)	−0.0030 (8)
C11	0.0555 (12)	0.0511 (12)	0.0367 (10)	−0.0066 (9)	0.0028 (8)	0.0085 (9)
C12	0.0674 (14)	0.0595 (14)	0.0522 (12)	0.0037 (11)	−0.0045 (10)	0.0076 (10)
C13	0.0725 (17)	0.097 (2)	0.0744 (16)	0.0257 (15)	−0.0086 (14)	0.0201 (15)
C14	0.0660 (17)	0.132 (3)	0.089 (2)	−0.0099 (18)	−0.0286 (14)	0.0353 (19)
C15	0.096 (2)	0.093 (2)	0.0634 (15)	−0.0412 (17)	−0.0263 (14)	0.0203 (14)
C16	0.0804 (16)	0.0612 (14)	0.0480 (12)	−0.0116 (12)	−0.0043 (11)	0.0079 (10)

Geometric parameters (Å, º)

O1—C1	1.230 (2)	C8—C9	1.388 (3)
O2—C3	1.416 (2)	C8—H8	0.93
O2—H2	0.94 (3)	C10—C11	1.509 (3)
C1—C9	1.463 (3)	C10—H10A	0.97
C1—C2	1.503 (2)	C10—H10B	0.97
C2—C2^i	1.357 (3)	C11—C16	1.391 (3)
C2—C3	1.540 (2)	C11—C12	1.391 (3)
C3—C4	1.505 (2)	C12—C13	1.375 (3)
C3—C10	1.551 (3)	C12—H12	0.93
C4—C9	1.386 (2)	C13—C14	1.377 (4)
C4—C5	1.392 (3)	C13—H13	0.93
C5—C6	1.384 (3)	C14—C15	1.380 (4)
C5—H5	0.93	C14—H14	0.93
C6—C7	1.398 (3)	C15—C16	1.379 (3)
C6—H6	0.93	C15—H15	0.93
C7—C8	1.387 (3)	C16—H16	0.93
C7—H7	0.93
C3—O2—H2	97.7 (17)	C4—C9—C8	122.49 (18)
O1—C1—C9	125.41 (17)	C4—C9—C1	109.42 (16)
O1—C1—C2	127.22 (18)	C8—C9—C1	128.08 (18)
C9—C1—C2	107.37 (15)	C11—C10—C3	114.99 (14)
C2^i—C2—C1	125.7 (2)	C11—C10—H10A	108.5
C2^i—C2—C3	127.1 (2)	C3—C10—H10A	108.5
C1—C2—C3	107.10 (15)	C11—C10—H10B	108.5
O2—C3—C4	108.23 (15)	C3—C10—H10B	108.5
O2—C3—C2	113.83 (14)	H10A—C10—H10B	107.5
C4—C3—C2	102.58 (14)	C16—C11—C12	118.09 (19)
O2—C3—C10	110.15 (14)	C16—C11—C10	121.10 (19)
C4—C3—C10	110.15 (14)	C12—C11—C10	120.81 (18)
C2—C3—C10	111.59 (14)	C13—C12—C11	121.0 (2)
C9—C4—C5	119.50 (18)	C13—C12—H12	119.5
C9—C4—C3	112.37 (15)	C11—C12—H12	119.5
C5—C4—C3	128.08 (17)	C12—C13—C14	120.0 (3)
C6—C5—C4	118.75 (19)	C12—C13—H13	120.0
C6—C5—H5	120.6	C14—C13—H13	120.0
C4—C5—H5	120.6	C13—C14—C15	120.2 (2)
C5—C6—C7	121.2 (2)	C13—C14—H14	119.9
C5—C6—H6	119.4	C15—C14—H14	119.9
C7—C6—H6	119.4	C16—C15—C14	119.6 (2)
C8—C7—C6	120.4 (2)	C16—C15—H15	120.2
C8—C7—H7	119.8	C14—C15—H15	120.2
C6—C7—H7	119.8	C15—C16—C11	121.1 (2)
C7—C8—C9	117.6 (2)	C15—C16—H16	119.4
C7—C8—H8	121.2	C11—C16—H16	119.4
C9—C8—H8	121.2
O1—C1—C2—C2^i	−9.8 (3)	C3—C4—C9—C8	−176.16 (16)
C9—C1—C2—C2^i	169.7 (2)	C5—C4—C9—C1	−177.29 (16)
O1—C1—C2—C3	172.19 (18)	C3—C4—C9—C1	5.0 (2)
C9—C1—C2—C3	−8.26 (18)	C7—C8—C9—C4	−1.7 (3)
C2^i—C2—C3—O2	−50.7 (3)	C7—C8—C9—C1	176.97 (19)
C1—C2—C3—O2	127.22 (16)	O1—C1—C9—C4	−178.18 (18)
C2^i—C2—C3—C4	−167.4 (2)	C2—C1—C9—C4	2.26 (19)
C1—C2—C3—C4	10.54 (17)	O1—C1—C9—C8	3.0 (3)
C2^i—C2—C3—C10	74.7 (3)	C2—C1—C9—C8	−176.53 (18)
C1—C2—C3—C10	−107.35 (16)	O2—C3—C10—C11	−175.53 (15)
O2—C3—C4—C9	−130.34 (16)	C4—C3—C10—C11	−56.2 (2)
C2—C3—C4—C9	−9.72 (18)	C2—C3—C10—C11	57.0 (2)
C10—C3—C4—C9	109.19 (16)	C3—C10—C11—C16	98.1 (2)
O2—C3—C4—C5	52.2 (2)	C3—C10—C11—C12	−81.8 (2)
C2—C3—C4—C5	172.78 (17)	C16—C11—C12—C13	−0.1 (3)
C10—C3—C4—C5	−68.3 (2)	C10—C11—C12—C13	179.85 (18)
C9—C4—C5—C6	−1.4 (3)	C11—C12—C13—C14	1.1 (3)
C3—C4—C5—C6	175.98 (17)	C12—C13—C14—C15	−1.0 (4)
C4—C5—C6—C7	1.4 (3)	C13—C14—C15—C16	−0.2 (4)
C5—C6—C7—C8	−1.5 (3)	C14—C15—C16—C11	1.2 (3)
C6—C7—C8—C9	1.6 (3)	C12—C11—C16—C15	−1.1 (3)
C5—C4—C9—C8	1.6 (3)	C10—C11—C16—C15	179.01 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.94 (3)	1.76 (3)	2.685 (2)	164 (3)
C5—H5···Cg1^ii	0.93	2.79	3.640 (3)	153

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y+1/2, −z+3/2.