(1SR,2RS,3SR,5SR,6RS)-6-[(Z)-1-Acet-oxy-2-phenyl-ethen-yl]-3-eth-oxy-2-phenyl-bicyclo-[3.1.0]hexan-1-yl acetate.

The mol-ecule of the title compound, C(26)H(28)O(5), is chiral with five stereogenic centres; however, the centrosymmetric triclinic group gives a racemic crystal. The fused ring system adopta boat conformation in which the cyclo-propane ring plane is roughly perpendicular to the styryl group plane, forming a dihedral angle of 74.78 (19)°. The dihedral angle between the two benzene rings is 77.24 (6)°.

Related literature

For related structures, see: Li et al. (2008 ▶); Zhang et al. (2008 ▶). For general backgound to the bicyclo­[3.1.0]hexane unit, see: Donaldson (2001 ▶); Ezzitouni & Marquez (1997 ▶); Hanessian et al. (1995 ▶); Monn et al. (1997 ▶).

Experimental

Crystal data

C26H28O5

M = 420.48

Triclinic,

a = 5.8585 (14) Å

b = 12.368 (3) Å

c = 15.852 (4) Å

α = 73.170 (6)°

β = 88.967 (9)°

γ = 81.761 (7)°

V = 1087.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 103 K

0.43 × 0.37 × 0.10 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

10211 measured reflections

4888 independent reflections

2841 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.076

S = 0.94

4888 reflections

277 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrystalClear (Rigaku, 2008) ▶; cell refinement: CrystalClear ▶; data reduction: CrystalClear ▶; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001760/kp2298sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001760/kp2298Isup2.hkl

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

C26H28O5	Z = 2
Mr = 420.48	F(000) = 448
Triclinic, P1	Dx = 1.284 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8585 (14) Å	Cell parameters from 3076 reflections
b = 12.368 (3) Å	θ = 3.3–27.5°
c = 15.852 (4) Å	µ = 0.09 mm−1
α = 73.170 (6)°	T = 103 K
β = 88.967 (9)°	Platelet, colourless
γ = 81.761 (7)°	0.43 × 0.37 × 0.10 mm
V = 1087.7 (4) Å3

Rigaku AFC10/Saturn724+ diffractometer	2841 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.053
graphite	θmax = 27.5°, θmin = 3.4°
Detector resolution: 28.5714 pixels mm-1	h = −7→7
φ and ω scans	k = −15→16
10211 measured reflections	l = −20→20
4888 independent reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0012P)2] where P = (Fo2 + 2Fc2)/3
4888 reflections	(Δ/σ)max < 0.001
277 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.32 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. 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	0.21125 (19)	0.60902 (10)	0.37934 (8)	0.0188 (3)
O2	0.45865 (19)	0.47059 (9)	0.15005 (8)	0.0165 (3)
O3	0.1062 (2)	0.41550 (10)	0.16972 (9)	0.0256 (3)
O4	0.34585 (18)	0.21945 (9)	0.34813 (8)	0.0171 (3)
O5	0.5217 (2)	0.17190 (10)	0.48169 (8)	0.0232 (3)
C20	0.4622 (3)	0.76441 (14)	0.12130 (12)	0.0190 (4)
H20	0.5858	0.7499	0.1629	0.023*
C19	0.4674 (3)	0.84861 (14)	0.04176 (12)	0.0234 (5)
H19	0.5936	0.8907	0.0291	0.028*
C18	0.2871 (3)	0.87087 (15)	−0.01919 (13)	0.0273 (5)
H18	0.2879	0.9290	−0.0736	0.033*
C17	0.1075 (3)	0.80827 (15)	−0.00027 (13)	0.0281 (5)
H17	−0.0155	0.8225	−0.0421	0.034*
C16	0.1049 (3)	0.72458 (14)	0.07945 (12)	0.0227 (5)
H16	−0.0210	0.6823	0.0918	0.027*
C15	0.2822 (3)	0.70114 (14)	0.14168 (12)	0.0167 (4)
C2	0.2748 (3)	0.60988 (13)	0.22886 (11)	0.0157 (4)
H2	0.1132	0.5928	0.2392	0.019*
C3	0.3613 (3)	0.64292 (14)	0.30821 (12)	0.0172 (4)
H3	0.3576	0.7276	0.2917	0.021*
C4	0.6121 (3)	0.58431 (14)	0.32826 (12)	0.0187 (4)
H4B	0.7208	0.6388	0.3026	0.022*
H4A	0.6422	0.5548	0.3927	0.022*
C5	0.6408 (3)	0.48698 (14)	0.28685 (11)	0.0162 (4)
H5	0.7961	0.4607	0.2668	0.019*
C1	0.4341 (3)	0.50053 (14)	0.23016 (12)	0.0151 (4)
C6	0.4684 (3)	0.40331 (13)	0.31560 (11)	0.0159 (4)
H6	0.3671	0.4142	0.3648	0.019*
C7	0.5228 (3)	0.28429 (14)	0.31184 (12)	0.0165 (4)
C8	0.7029 (3)	0.23893 (14)	0.27441 (11)	0.0170 (4)
H8	0.8082	0.2900	0.2483	0.020*
C21	0.7645 (3)	0.12233 (14)	0.26717 (11)	0.0170 (4)
C22	0.6235 (3)	0.03660 (14)	0.29030 (12)	0.0223 (5)
H22	0.4741	0.0525	0.3120	0.027*
C23	0.6990 (3)	−0.07128 (15)	0.28197 (13)	0.0267 (5)
H23	0.6016	−0.1287	0.2987	0.032*
C24	0.9144 (3)	−0.09582 (16)	0.24957 (13)	0.0270 (5)
H24	0.9652	−0.1698	0.2438	0.032*
C25	1.0556 (3)	−0.01220 (15)	0.22559 (13)	0.0260 (5)
H25	1.2032	−0.0282	0.2025	0.031*
C26	0.9818 (3)	0.09516 (15)	0.23522 (12)	0.0213 (4)
H26	1.0818	0.1515	0.2197	0.026*
C11	0.2788 (3)	0.42436 (14)	0.12820 (13)	0.0197 (4)
C12	0.3253 (3)	0.38905 (16)	0.04671 (13)	0.0330 (5)
H12A	0.2224	0.3345	0.0432	0.050*
H12B	0.4861	0.3531	0.0482	0.050*
H12C	0.2980	0.4563	−0.0050	0.050*
C13	0.2398 (3)	0.66215 (15)	0.44723 (12)	0.0233 (5)
H13B	0.2472	0.7445	0.4205	0.028*
H13A	0.3856	0.6268	0.4809	0.028*
C14	0.0379 (3)	0.64685 (15)	0.50811 (12)	0.0252 (5)
H14B	−0.1054	0.6839	0.4747	0.038*
H14C	0.0576	0.6815	0.5553	0.038*
H14A	0.0306	0.5652	0.5338	0.038*
C9	0.3658 (3)	0.16383 (15)	0.43626 (13)	0.0232 (3)
C10	0.1810 (3)	0.09224 (14)	0.46514 (12)	0.0238 (5)
H10A	0.2242	0.0190	0.4527	0.036*
H10B	0.0368	0.1314	0.4332	0.036*
H10C	0.1596	0.0789	0.5286	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0232 (7)	0.0222 (7)	0.0138 (7)	−0.0053 (5)	0.0043 (6)	−0.0089 (5)
O2	0.0212 (7)	0.0178 (7)	0.0129 (7)	−0.0046 (5)	0.0043 (5)	−0.0074 (5)
O3	0.0225 (8)	0.0344 (8)	0.0250 (9)	−0.0116 (6)	0.0070 (6)	−0.0136 (6)
O4	0.0179 (7)	0.0180 (7)	0.0145 (7)	−0.0047 (5)	0.0036 (5)	−0.0027 (5)
O5	0.0286 (7)	0.0221 (6)	0.0192 (7)	−0.0072 (5)	0.0001 (5)	−0.0048 (5)
C20	0.0194 (11)	0.0189 (10)	0.0188 (11)	−0.0030 (8)	0.0000 (8)	−0.0055 (8)
C19	0.0256 (11)	0.0197 (10)	0.0247 (12)	−0.0077 (8)	0.0051 (9)	−0.0042 (8)
C18	0.0338 (12)	0.0198 (10)	0.0227 (12)	−0.0022 (9)	0.0013 (10)	0.0015 (8)
C17	0.0280 (12)	0.0317 (12)	0.0213 (13)	−0.0041 (10)	−0.0042 (9)	−0.0022 (9)
C16	0.0177 (10)	0.0239 (10)	0.0252 (12)	−0.0052 (8)	−0.0006 (9)	−0.0041 (9)
C15	0.0208 (10)	0.0139 (9)	0.0169 (11)	−0.0004 (8)	0.0028 (8)	−0.0079 (8)
C2	0.0177 (10)	0.0164 (9)	0.0154 (11)	−0.0055 (8)	0.0046 (8)	−0.0074 (8)
C3	0.0213 (11)	0.0168 (9)	0.0155 (11)	−0.0062 (8)	0.0031 (8)	−0.0062 (8)
C4	0.0177 (10)	0.0176 (10)	0.0215 (11)	−0.0019 (8)	0.0002 (8)	−0.0069 (8)
C5	0.0138 (10)	0.0177 (10)	0.0184 (11)	−0.0030 (8)	0.0032 (8)	−0.0073 (8)
C1	0.0195 (10)	0.0160 (9)	0.0113 (10)	−0.0027 (8)	0.0037 (8)	−0.0064 (7)
C6	0.0199 (10)	0.0165 (9)	0.0120 (10)	−0.0038 (8)	0.0056 (8)	−0.0048 (7)
C7	0.0172 (10)	0.0178 (10)	0.0135 (10)	−0.0050 (8)	0.0002 (8)	−0.0019 (8)
C8	0.0166 (10)	0.0173 (9)	0.0170 (11)	−0.0050 (8)	0.0017 (8)	−0.0035 (8)
C21	0.0186 (10)	0.0169 (10)	0.0147 (11)	−0.0017 (8)	−0.0016 (8)	−0.0040 (8)
C22	0.0187 (11)	0.0208 (10)	0.0288 (13)	−0.0017 (8)	0.0017 (9)	−0.0099 (9)
C23	0.0288 (12)	0.0196 (10)	0.0340 (13)	−0.0059 (9)	0.0003 (10)	−0.0104 (9)
C24	0.0286 (12)	0.0195 (10)	0.0351 (14)	0.0035 (9)	−0.0056 (10)	−0.0143 (9)
C25	0.0194 (11)	0.0274 (11)	0.0326 (13)	0.0034 (9)	−0.0017 (9)	−0.0139 (9)
C26	0.0209 (11)	0.0208 (10)	0.0223 (12)	−0.0031 (8)	0.0003 (9)	−0.0065 (8)
C11	0.0254 (12)	0.0168 (10)	0.0185 (11)	−0.0076 (8)	0.0024 (9)	−0.0056 (8)
C12	0.0468 (14)	0.0389 (13)	0.0250 (13)	−0.0217 (11)	0.0146 (10)	−0.0207 (10)
C13	0.0324 (12)	0.0245 (11)	0.0157 (11)	−0.0038 (9)	0.0010 (9)	−0.0104 (8)
C14	0.0306 (12)	0.0274 (11)	0.0188 (12)	0.0013 (9)	0.0018 (9)	−0.0114 (9)
C9	0.0286 (7)	0.0221 (6)	0.0192 (7)	−0.0072 (5)	0.0001 (5)	−0.0048 (5)
C10	0.0272 (11)	0.0192 (10)	0.0232 (12)	−0.0074 (8)	0.0055 (9)	−0.0014 (8)

O1—C3	1.420 (2)	C1—C6	1.523 (2)
O1—C13	1.4372 (19)	C6—C7	1.479 (2)
O2—C11	1.363 (2)	C6—H6	1.0000
O2—C1	1.4215 (19)	C7—C8	1.334 (2)
O3—C11	1.198 (2)	C8—C21	1.473 (2)
O4—C9	1.366 (2)	C8—H8	0.9500
O4—C7	1.414 (2)	C21—C26	1.394 (2)
O5—C9	1.2057 (18)	C21—C22	1.398 (2)
C20—C15	1.381 (2)	C22—C23	1.387 (2)
C20—C19	1.387 (2)	C22—H22	0.9500
C20—H20	0.9500	C23—C24	1.381 (3)
C19—C18	1.387 (2)	C23—H23	0.9500
C19—H19	0.9500	C24—C25	1.380 (2)
C18—C17	1.373 (2)	C24—H24	0.9500
C18—H18	0.9500	C25—C26	1.387 (2)
C17—C16	1.384 (2)	C25—H25	0.9500
C17—H17	0.9500	C26—H26	0.9500
C16—C15	1.386 (2)	C11—C12	1.488 (2)
C16—H16	0.9500	C12—H12A	0.9800
C15—C2	1.515 (2)	C12—H12B	0.9800
C2—C1	1.524 (2)	C12—H12C	0.9800
C2—C3	1.545 (2)	C13—C14	1.511 (3)
C2—H2	1.0000	C13—H13B	0.9900
C3—C4	1.538 (2)	C13—H13A	0.9900
C3—H3	1.0000	C14—H14B	0.9800
C4—C5	1.518 (2)	C14—H14C	0.9800
C4—H4B	0.9900	C14—H14A	0.9800
C4—H4A	0.9900	C9—C10	1.479 (2)
C5—C1	1.482 (2)	C10—H10A	0.9800
C5—C6	1.519 (2)	C10—H10B	0.9800
C5—H5	1.0000	C10—H10C	0.9800
C3—O1—C13	112.11 (13)	C1—C6—H6	115.3
C11—O2—C1	114.87 (14)	C8—C7—O4	120.48 (15)
C9—O4—C7	116.41 (12)	C8—C7—C6	127.71 (17)
C15—C20—C19	121.78 (16)	O4—C7—C6	111.64 (15)
C15—C20—H20	119.1	C7—C8—C21	130.31 (17)
C19—C20—H20	119.1	C7—C8—H8	114.8
C20—C19—C18	119.51 (18)	C21—C8—H8	114.8
C20—C19—H19	120.2	C26—C21—C22	117.45 (16)
C18—C19—H19	120.2	C26—C21—C8	117.21 (16)
C17—C18—C19	119.49 (18)	C22—C21—C8	125.33 (17)
C17—C18—H18	120.3	C23—C22—C21	120.89 (18)
C19—C18—H18	120.3	C23—C22—H22	119.6
C18—C17—C16	120.24 (17)	C21—C22—H22	119.6
C18—C17—H17	119.9	C24—C23—C22	120.54 (18)
C16—C17—H17	119.9	C24—C23—H23	119.7
C17—C16—C15	121.40 (18)	C22—C23—H23	119.7
C17—C16—H16	119.3	C25—C24—C23	119.54 (17)
C15—C16—H16	119.3	C25—C24—H24	120.2
C20—C15—C16	117.56 (17)	C23—C24—H24	120.2
C20—C15—C2	121.91 (15)	C24—C25—C26	119.97 (19)
C16—C15—C2	120.53 (16)	C24—C25—H25	120.0
C15—C2—C1	111.54 (15)	C26—C25—H25	120.0
C15—C2—C3	113.55 (14)	C25—C26—C21	121.60 (17)
C1—C2—C3	103.93 (12)	C25—C26—H26	119.2
C15—C2—H2	109.2	C21—C26—H26	119.2
C1—C2—H2	109.2	O3—C11—O2	123.27 (17)
C3—C2—H2	109.2	O3—C11—C12	125.48 (17)
O1—C3—C4	113.68 (14)	O2—C11—C12	111.24 (16)
O1—C3—C2	108.36 (13)	C11—C12—H12A	109.5
C4—C3—C2	106.92 (14)	C11—C12—H12B	109.5
O1—C3—H3	109.3	H12A—C12—H12B	109.5
C4—C3—H3	109.3	C11—C12—H12C	109.5
C2—C3—H3	109.3	H12A—C12—H12C	109.5
C5—C4—C3	106.17 (13)	H12B—C12—H12C	109.5
C5—C4—H4B	110.5	O1—C13—C14	108.95 (14)
C3—C4—H4B	110.5	O1—C13—H13B	109.9
C5—C4—H4A	110.5	C14—C13—H13B	109.9
C3—C4—H4A	110.5	O1—C13—H13A	109.9
H4B—C4—H4A	108.7	C14—C13—H13A	109.9
C1—C5—C4	107.90 (14)	H13B—C13—H13A	108.3
C1—C5—C6	60.96 (10)	C13—C14—H14B	109.5
C4—C5—C6	115.09 (16)	C13—C14—H14C	109.5
C1—C5—H5	119.6	H14B—C14—H14C	109.5
C4—C5—H5	119.6	C13—C14—H14A	109.5
C6—C5—H5	119.6	H14B—C14—H14A	109.5
O2—C1—C5	119.36 (14)	H14C—C14—H14A	109.5
O2—C1—C6	117.08 (14)	O5—C9—O4	122.20 (18)
C5—C1—C6	60.72 (10)	O5—C9—C10	126.33 (18)
O2—C1—C2	117.65 (13)	O4—C9—C10	111.43 (14)
C5—C1—C2	110.21 (14)	C9—C10—H10A	109.5
C6—C1—C2	119.07 (15)	C9—C10—H10B	109.5
C7—C6—C5	121.31 (16)	H10A—C10—H10B	109.5
C7—C6—C1	119.45 (15)	C9—C10—H10C	109.5
C5—C6—C1	58.32 (11)	H10A—C10—H10C	109.5
C7—C6—H6	115.3	H10B—C10—H10C	109.5
C5—C6—H6	115.3
C15—C20—C19—C18	0.3 (3)	C15—C2—C1—C6	173.81 (14)
C20—C19—C18—C17	−0.8 (3)	C3—C2—C1—C6	51.09 (19)
C19—C18—C17—C16	0.8 (3)	C1—C5—C6—C7	107.50 (18)
C18—C17—C16—C15	−0.4 (3)	C4—C5—C6—C7	−155.14 (15)
C19—C20—C15—C16	0.0 (3)	C4—C5—C6—C1	97.36 (16)
C19—C20—C15—C2	−179.41 (17)	O2—C1—C6—C7	−0.5 (2)
C17—C16—C15—C20	0.0 (3)	C5—C1—C6—C7	−110.66 (18)
C17—C16—C15—C2	179.45 (17)	C2—C1—C6—C7	151.20 (15)
C20—C15—C2—C1	−77.7 (2)	O2—C1—C6—C5	110.16 (16)
C16—C15—C2—C1	102.84 (19)	C2—C1—C6—C5	−98.13 (17)
C20—C15—C2—C3	39.3 (2)	C9—O4—C7—C8	94.3 (2)
C16—C15—C2—C3	−140.13 (17)	C9—O4—C7—C6	−90.12 (17)
C13—O1—C3—C4	76.72 (17)	C5—C6—C7—C8	−9.5 (3)
C13—O1—C3—C2	−164.57 (12)	C1—C6—C7—C8	59.3 (2)
C15—C2—C3—O1	137.72 (15)	C5—C6—C7—O4	175.32 (14)
C1—C2—C3—O1	−100.89 (15)	C1—C6—C7—O4	−115.93 (17)
C15—C2—C3—C4	−99.37 (17)	O4—C7—C8—C21	−4.1 (3)
C1—C2—C3—C4	22.01 (18)	C6—C7—C8—C21	−178.87 (15)
O1—C3—C4—C5	99.09 (17)	C7—C8—C21—C26	−170.96 (17)
C2—C3—C4—C5	−20.44 (18)	C7—C8—C21—C22	8.6 (3)
C3—C4—C5—C1	10.56 (19)	C26—C21—C22—C23	0.3 (3)
C3—C4—C5—C6	−55.11 (19)	C8—C21—C22—C23	−179.20 (16)
C11—O2—C1—C5	144.83 (15)	C21—C22—C23—C24	−0.8 (3)
C11—O2—C1—C6	74.86 (18)	C22—C23—C24—C25	0.2 (3)
C11—O2—C1—C2	−77.26 (18)	C23—C24—C25—C26	0.9 (3)
C4—C5—C1—O2	144.23 (15)	C24—C25—C26—C21	−1.3 (3)
C6—C5—C1—O2	−106.47 (17)	C22—C21—C26—C25	0.7 (3)
C4—C5—C1—C6	−109.30 (17)	C8—C21—C26—C25	−179.71 (16)
C4—C5—C1—C2	3.5 (2)	C1—O2—C11—O3	4.4 (2)
C6—C5—C1—C2	112.78 (17)	C1—O2—C11—C12	−176.47 (14)
C15—C2—C1—O2	−34.6 (2)	C3—O1—C13—C14	165.68 (14)
C3—C2—C1—O2	−157.36 (14)	C7—O4—C9—O5	2.2 (3)
C15—C2—C1—C5	106.86 (16)	C7—O4—C9—C10	−175.71 (14)
C3—C2—C1—C5	−15.86 (19)