(1S*,4S*,5R*,8R*)-4,8-Di­phenyl-3,7-dioxa­bi­cyclo­[3.3.0]­octan-2-one

Gelbrich, T.; Hursthouse, M.B.

doi:10.1107/S1600536801008170

(1S,4S,5R,8R)-4,8-Diphenyl-3,7-dioxabicyclo[3.3.0]octan-2-one

The title compound, C₁₈H₁₆O₃, (I), was prepared in the course of studies towards the synthesis of furofuran ligands and was reported previously [Brown & Hinks (1998). Chem. Commun. pp. 1895-1896]. The compound is a a model system, where both oxygenated aromatic rings that are present in the natural products have been substituted by a simple phenyl group.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008170/cv6025sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008170/cv6025Isup2.hkl Contains datablock I

CCDC reference: 170753

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Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R factor = 0.051
wR factor = 0.109
Data-to-parameter ratio = 12.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

NO COMMENT

Experimental top

The furofuranone was recrystallized from Et₂O/hexanes as colourless crystals.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

Figures top

Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids.

(1S*,4S*,5R*,8R*)-4,8-Diphenyl-3,7-dioxabicyclo[3.3.0]octan-2-one top

Crystal data top

C₁₈H₁₆O₃	F(000) = 1184
M_r = 280.31	D_x = 1.342 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.416 (1) Å	Cell parameters from 8593 reflections
b = 7.520 (1) Å	θ = 2.9–25.2°
c = 19.487 (1) Å	µ = 0.09 mm⁻¹
β = 117.86 (1)°	T = 150 K
V = 2774.7 (3) Å³	Block, colourless
Z = 8	0.30 × 0.20 × 0.15 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	2489 independent reflections
Radiation source: Nonius FR591 rotating anode	1822 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ϕ and ω scans to fill Ewald sphere	θ_max = 25.3°, θ_min = 2.9°
Absorption correction: multi-scan (Blessing, 1997)	h = −24→25
T_min = 0.973, T_max = 0.987	k = −9→8
7164 measured reflections	l = −23→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0009P)² + 5.P] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.003
2489 reflections	Δρ_max = 0.25 e Å⁻³
207 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0062 (5)

Crystal data top

C₁₈H₁₆O₃	V = 2774.7 (3) Å³
M_r = 280.31	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.416 (1) Å	µ = 0.09 mm⁻¹
b = 7.520 (1) Å	T = 150 K
c = 19.487 (1) Å	0.30 × 0.20 × 0.15 mm
β = 117.86 (1)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2489 independent reflections
Absorption correction: multi-scan (Blessing, 1997)	1822 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.987	R_int = 0.067
7164 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 0.97	Δρ_max = 0.25 e Å⁻³
2489 reflections	Δρ_min = −0.22 e Å⁻³
207 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.07450 (7)	0.2916 (2)	0.34285 (9)	0.0348 (4)
O2	0.22067 (7)	0.0174 (2)	0.46476 (9)	0.0354 (4)
O3	0.00184 (7)	0.0704 (2)	0.33285 (9)	0.0382 (4)
C1	0.05818 (11)	0.1159 (3)	0.33989 (12)	0.0302 (5)
C2	0.11744 (11)	0.0022 (3)	0.34348 (13)	0.0315 (5)
H2	0.0998	−0.0823	0.2987	0.046 (7)*
C3	0.17074 (10)	0.1339 (3)	0.33991 (13)	0.0312 (5)
H3	0.1720	0.1287	0.2893	0.037 (6)*
C4	0.14588 (10)	0.3167 (3)	0.35418 (13)	0.0302 (5)
H4	0.1767	0.3511	0.4095	0.023 (5)*
C5	0.16173 (10)	−0.0976 (3)	0.42139 (13)	0.0315 (5)
H5	0.1805	−0.2086	0.4094	0.028 (5)*
C6	0.24032 (11)	0.0813 (3)	0.40766 (14)	0.0371 (6)
H6A	0.2637	−0.0133	0.3926	0.044 (7)*
H6B	0.2725	0.1847	0.4276	0.040 (6)*
C7	0.08997 (11)	0.5192 (3)	0.23582 (13)	0.0350 (6)
H7	0.0452	0.4661	0.2210	0.042 (6)*
C8	0.09694 (12)	0.6527 (3)	0.19024 (14)	0.0409 (6)
H8	0.0567	0.6921	0.1448	0.044 (7)*
C9	0.16205 (12)	0.7277 (3)	0.21082 (15)	0.0410 (6)
H9	0.1666	0.8167	0.1788	0.042 (6)*
C10	0.22031 (12)	0.6746 (3)	0.27718 (15)	0.0396 (6)
H10	0.2651	0.7269	0.2913	0.042 (6)*
C11	0.21346 (11)	0.5436 (3)	0.32364 (14)	0.0360 (6)
H11	0.2536	0.5082	0.3701	0.034 (6)*
C12	0.14846 (11)	0.4642 (3)	0.30268 (13)	0.0299 (5)
C13	0.11114 (11)	−0.3256 (3)	0.47345 (15)	0.0408 (6)
H13	0.1217	−0.4113	0.4445	0.050 (7)*
C14	0.08009 (13)	−0.3801 (3)	0.51884 (17)	0.0519 (7)
H14	0.0699	−0.5022	0.5212	0.076 (9)*
C15	0.06434 (12)	−0.2559 (3)	0.56027 (15)	0.0451 (6)
H15	0.0435	−0.2923	0.5916	0.063 (8)*
C16	0.07874 (11)	−0.0796 (3)	0.55638 (13)	0.0392 (6)
H16	0.0674	0.0057	0.5848	0.065 (8)*
C17	0.10979 (11)	−0.0244 (3)	0.51127 (13)	0.0337 (5)
H17	0.1194	0.0981	0.5087	0.038 (6)*
C18	0.12677 (10)	−0.1495 (3)	0.46991 (12)	0.0296 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0270 (8)	0.0444 (9)	0.0465 (10)	0.0046 (7)	0.0283 (8)	0.0013 (7)
O2	0.0220 (8)	0.0508 (10)	0.0411 (10)	0.0004 (7)	0.0212 (7)	0.0031 (7)
O3	0.0243 (8)	0.0625 (11)	0.0359 (9)	−0.0014 (7)	0.0207 (7)	0.0014 (8)
C1	0.0246 (11)	0.0493 (14)	0.0230 (12)	0.0006 (10)	0.0163 (10)	−0.0008 (10)
C2	0.0278 (11)	0.0422 (13)	0.0348 (13)	−0.0013 (9)	0.0234 (10)	−0.0050 (10)
C3	0.0285 (12)	0.0399 (12)	0.0387 (13)	0.0015 (9)	0.0269 (11)	−0.0023 (10)
C4	0.0228 (11)	0.0424 (13)	0.0327 (13)	0.0013 (9)	0.0192 (10)	−0.0041 (10)
C5	0.0238 (11)	0.0390 (13)	0.0409 (13)	0.0017 (9)	0.0227 (10)	−0.0020 (10)
C6	0.0279 (12)	0.0450 (14)	0.0533 (16)	0.0044 (10)	0.0313 (12)	0.0052 (11)
C7	0.0278 (12)	0.0402 (13)	0.0419 (14)	−0.0050 (10)	0.0203 (11)	−0.0033 (10)
C8	0.0367 (14)	0.0466 (14)	0.0395 (15)	−0.0004 (11)	0.0179 (12)	0.0020 (11)
C9	0.0439 (15)	0.0425 (14)	0.0526 (16)	−0.0018 (11)	0.0358 (14)	0.0006 (12)
C10	0.0315 (13)	0.0448 (14)	0.0566 (17)	−0.0054 (10)	0.0323 (13)	−0.0075 (12)
C11	0.0243 (12)	0.0481 (14)	0.0417 (14)	0.0032 (10)	0.0205 (11)	−0.0023 (11)
C12	0.0271 (11)	0.0355 (12)	0.0380 (13)	0.0002 (9)	0.0242 (11)	−0.0062 (10)
C13	0.0369 (13)	0.0411 (14)	0.0598 (17)	0.0092 (10)	0.0355 (13)	0.0052 (11)
C14	0.0507 (16)	0.0444 (16)	0.082 (2)	0.0097 (12)	0.0494 (16)	0.0166 (14)
C15	0.0364 (14)	0.0622 (17)	0.0509 (16)	0.0089 (12)	0.0324 (13)	0.0129 (13)
C16	0.0245 (12)	0.0631 (16)	0.0375 (14)	−0.0006 (11)	0.0207 (11)	−0.0058 (12)
C17	0.0252 (11)	0.0439 (14)	0.0385 (14)	−0.0022 (10)	0.0202 (11)	−0.0053 (10)
C18	0.0191 (10)	0.0397 (13)	0.0346 (13)	0.0055 (9)	0.0163 (10)	0.0021 (10)

Geometric parameters (Å, º) top

O1—C1	1.361 (3)	C7—H7	0.9500
O1—C4	1.451 (2)	C8—C9	1.379 (3)
O2—C5	1.435 (2)	C8—H8	0.9500
O2—C6	1.444 (2)	C9—C10	1.371 (3)
O3—C1	1.199 (2)	C9—H9	0.9500
C1—C2	1.505 (3)	C10—C11	1.391 (3)
C2—C3	1.537 (3)	C10—H10	0.9500
C2—C5	1.556 (3)	C11—C12	1.389 (3)
C2—H2	1.0000	C11—H11	0.9500
C3—C6	1.510 (3)	C13—C18	1.376 (3)
C3—C4	1.546 (3)	C13—C14	1.394 (3)
C3—H3	1.0000	C13—H13	0.9500
C4—C12	1.514 (3)	C14—C15	1.376 (3)
C4—H4	1.0000	C14—H14	0.9500
C5—C18	1.506 (3)	C15—C16	1.372 (3)
C5—H5	1.0000	C15—H15	0.9500
C6—H6A	0.9900	C16—C17	1.391 (3)
C6—H6B	0.9900	C16—H16	0.9500
C7—C12	1.383 (3)	C17—C18	1.393 (3)
C7—C8	1.394 (3)	C17—H17	0.9500

C1—O1—C4	111.34 (15)	C12—C7—H7	120.1
C5—O2—C6	103.87 (16)	C8—C7—H7	120.1
O3—C1—O1	120.45 (19)	C9—C8—C7	120.3 (2)
O3—C1—C2	128.7 (2)	C9—C8—H8	119.9
O1—C1—C2	110.84 (16)	C7—C8—H8	119.9
C1—C2—C3	105.06 (17)	C10—C9—C8	120.4 (2)
C1—C2—C5	115.83 (17)	C10—C9—H9	119.8
C3—C2—C5	103.17 (17)	C8—C9—H9	119.8
C1—C2—H2	110.8	C9—C10—C11	119.6 (2)
C3—C2—H2	110.8	C9—C10—H10	120.2
C5—C2—H2	110.8	C11—C10—H10	120.2
C6—C3—C2	104.00 (17)	C12—C11—C10	120.6 (2)
C6—C3—C4	110.95 (18)	C12—C11—H11	119.7
C2—C3—C4	103.84 (15)	C10—C11—H11	119.7
C6—C3—H3	112.5	C7—C12—C11	119.4 (2)
C2—C3—H3	112.5	C7—C12—C4	123.08 (18)
C4—C3—H3	112.5	C11—C12—C4	117.5 (2)
O1—C4—C12	110.89 (16)	C18—C13—C14	120.9 (2)
O1—C4—C3	106.50 (16)	C18—C13—H13	119.5
C12—C4—C3	114.20 (16)	C14—C13—H13	119.5
O1—C4—H4	108.4	C15—C14—C13	119.6 (2)
C12—C4—H4	108.4	C15—C14—H14	120.2
C3—C4—H4	108.4	C13—C14—H14	120.2
O2—C5—C18	110.18 (17)	C16—C15—C14	120.1 (2)
O2—C5—C2	104.57 (16)	C16—C15—H15	120.0
C18—C5—C2	118.83 (16)	C14—C15—H15	120.0
O2—C5—H5	107.6	C15—C16—C17	120.6 (2)
C18—C5—H5	107.6	C15—C16—H16	119.7
C2—C5—H5	107.6	C17—C16—H16	119.7
O2—C6—C3	103.71 (15)	C16—C17—C18	119.7 (2)
O2—C6—H6A	111.0	C16—C17—H17	120.1
C3—C6—H6A	111.0	C18—C17—H17	120.1
O2—C6—H6B	111.0	C13—C18—C17	119.1 (2)
C3—C6—H6B	111.0	C13—C18—C5	119.00 (19)
H6A—C6—H6B	109.0	C17—C18—C5	121.9 (2)
C12—C7—C8	119.7 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆O₃
M_r	280.31
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	21.416 (1), 7.520 (1), 19.487 (1)
β (°)	117.86 (1)
V (Å³)	2774.7 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (Blessing, 1997)
T_min, T_max	0.973, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	7164, 2489, 1822
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.109, 0.97
No. of reflections	2489
No. of parameters	207
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.22

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1990).

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(1S*,4S*,5R*,8R*)-4,8-Di­phenyl-3,7-dioxa­bi­cyclo­[3.3.0]­octan-2-one

Supporting information

Key indicators

checkCIF results

(1S,4S,5R,8R)-4,8-Diphenyl-3,7-dioxabicyclo[3.3.0]octan-2-one