(5SR,6RS)-6-Phenyl-5-(phenyl­sulfonylacetyl)­bi­cyclo­[2.2.1]­hept-2-ene

The title compound, C₂₁H₂₀O₃S, was obtained from the Diels-Alder reaction of 4-phenyl-1-phenyl­sulfonyl-3-buten-2-one and cyclo­penta­diene, catalyzed by a titanium reagent. This mol­ecule is an endo-cyclo­adduct isomer.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.103
• Data-to-parameter ratio = 10.9

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: Please provide missing details; software used to prepare material for publication: CrystalStructure.

(5SR,6RS)-6-Phenyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene

Crystal data

C21H20O3S	Z = 2
Mr = 352.45	F(000) = 372.00
Triclinic, P1	Dx = 1.351 Mg m^−3
Hall symbol: -P 1	Melting point: 114 K
a = 8.6363 (3) Å	Mo Kα radiation, λ = 0.7107 Å
b = 9.6144 (3) Å	Cell parameters from 3777 reflections
c = 12.0887 (4) Å	θ = 3.4–27.5°
α = 107.319 (1)°	µ = 0.20 mm^−1
β = 104.509 (1)°	T = 297 K
γ = 104.8535 (9)°	Chunk, colourless
V = 866.19 (5) Å^3	0.40 × 0.35 × 0.28 mm

Data collection

Rigaku RAXIS-RAPID diffractometer	2686 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.014
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.857, Tmax = 0.945	k = −12→12
16666 measured reflections	l = −15→13
3939 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = (4Fo^2)/[0.0016Fo^2 + 3σ(Fo^2)]
wR(F^2) = 0.103	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.22 e Å^−3
2689 reflections	Δρmin = −0.47 e Å^−3
246 parameters

Special details

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.73894 (6)	0.26591 (5)	1.05507 (4)	0.0446 (1)
O1	1.0066 (2)	0.1685 (2)	0.9258 (1)	0.0641 (4)
O2	0.6423 (2)	0.2280 (2)	1.1297 (1)	0.0646 (5)
O3	0.9051 (2)	0.3846 (1)	1.1141 (1)	0.0629 (4)
C1	0.7555 (2)	0.0873 (2)	0.9701 (1)	0.0418 (4)
C2	0.8550 (2)	0.0961 (2)	0.8828 (1)	0.0395 (4)
C3	0.7559 (2)	0.0062 (2)	0.7468 (1)	0.0352 (4)
C4	0.6658 (2)	−0.1721 (2)	0.7160 (1)	0.0432 (4)
C5	0.8071 (2)	−0.2268 (2)	0.7644 (2)	0.0488 (5)
C6	0.8995 (3)	−0.2266 (2)	0.6924 (2)	0.0505 (5)
C7	0.8228 (2)	−0.1723 (2)	0.5943 (1)	0.0437 (5)
C8	0.6325 (2)	−0.2372 (2)	0.5763 (1)	0.0480 (5)
C9	0.8665 (2)	0.0054 (2)	0.6627 (1)	0.0361 (4)
C10	0.8361 (2)	0.0979 (2)	0.5828 (1)	0.0356 (4)
C11	0.7567 (2)	0.0302 (2)	0.4542 (1)	0.0461 (5)
C12	0.7344 (2)	0.1201 (2)	0.3859 (2)	0.0521 (5)
C13	0.7900 (2)	0.2794 (2)	0.4431 (2)	0.0537 (6)
C14	0.8685 (3)	0.3489 (2)	0.5705 (2)	0.0518 (5)
C15	0.8907 (2)	0.2584 (2)	0.6386 (1)	0.0437 (5)
C16	0.6146 (2)	0.3137 (2)	0.9428 (1)	0.0408 (4)
C17	0.6921 (3)	0.3865 (2)	0.8774 (2)	0.0514 (5)
C18	0.5931 (3)	0.4247 (2)	0.7908 (2)	0.0642 (7)
C19	0.4220 (3)	0.3954 (2)	0.7734 (2)	0.0653 (6)
C20	0.3483 (3)	0.3260 (2)	0.8402 (2)	0.0630 (6)
C21	0.4431 (2)	0.2832 (2)	0.9246 (2)	0.0507 (5)
H1	0.8097	0.0521	1.0269	0.051*
H2	0.6451	0.0157	0.9232	0.050*
H3	0.6739	0.0480	0.7219	0.043*
H4	0.5706	−0.1974	0.7391	0.049*
H5	0.8279	−0.2537	0.8331	0.059*
H6	0.9941	−0.2573	0.6995	0.065*
H7	0.8512	−0.2001	0.5236	0.053*
H8	0.5850	−0.3455	0.5397	0.053*
H9	0.5667	−0.1955	0.5318	0.052*
H10	0.9811	0.0497	0.7139	0.042*
H11	0.7160	−0.0778	0.4140	0.052*
H12	0.6836	0.0719	0.3001	0.063*
H13	0.7735	0.3386	0.3958	0.072*
H14	0.9083	0.4569	0.6103	0.065*
H15	0.9405	0.3053	0.7245	0.053*
H16	0.8085	0.4091	0.8925	0.063*
H17	0.6416	0.4693	0.7433	0.080*
H18	0.3569	0.4257	0.7177	0.073*
H19	0.2328	0.3060	0.8279	0.069*
H20	0.3928	0.2330	0.9686	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0539 (3)	0.0453 (3)	0.0340 (2)	0.0189 (2)	0.0192 (2)	0.0105 (2)
O1	0.0442 (7)	0.081 (1)	0.0418 (7)	0.0025 (7)	0.0151 (6)	0.0068 (7)
O2	0.092 (1)	0.082 (1)	0.0494 (7)	0.0466 (9)	0.0471 (7)	0.0328 (7)
O3	0.0583 (8)	0.0494 (8)	0.0528 (7)	0.0132 (6)	0.0022 (6)	0.0019 (6)
C1	0.050 (1)	0.0394 (9)	0.0369 (8)	0.0149 (8)	0.0199 (8)	0.0137 (7)
C2	0.0421 (9)	0.0376 (9)	0.0393 (8)	0.0131 (7)	0.0187 (7)	0.0129 (7)
C3	0.0356 (8)	0.0363 (8)	0.0362 (8)	0.0135 (7)	0.0161 (7)	0.0140 (7)
C4	0.0418 (9)	0.0386 (9)	0.0433 (9)	0.0047 (7)	0.0194 (7)	0.0125 (7)
C5	0.060 (1)	0.0357 (9)	0.053 (1)	0.0143 (8)	0.0239 (9)	0.0196 (8)
C6	0.062 (1)	0.0394 (9)	0.061 (1)	0.0257 (8)	0.0295 (9)	0.0215 (8)
C7	0.054 (1)	0.0375 (9)	0.0412 (8)	0.0160 (8)	0.0248 (8)	0.0111 (7)
C8	0.052 (1)	0.0358 (9)	0.0434 (9)	0.0043 (8)	0.0185 (8)	0.0070 (8)
C9	0.0360 (8)	0.0351 (8)	0.0355 (8)	0.0107 (7)	0.0165 (7)	0.0101 (7)
C10	0.0345 (8)	0.0371 (8)	0.0360 (8)	0.0115 (7)	0.0175 (7)	0.0124 (7)
C11	0.050 (1)	0.0415 (9)	0.0393 (8)	0.0092 (8)	0.0170 (8)	0.0114 (8)
C12	0.052 (1)	0.065 (1)	0.0403 (9)	0.0184 (9)	0.0174 (8)	0.0242 (9)
C13	0.053 (1)	0.064 (1)	0.064 (1)	0.028 (1)	0.0293 (9)	0.039 (1)
C14	0.059 (1)	0.040 (1)	0.063 (1)	0.0195 (9)	0.0296 (9)	0.0215 (9)
C15	0.051 (1)	0.0384 (9)	0.0419 (9)	0.0152 (8)	0.0208 (8)	0.0121 (7)
C16	0.0475 (9)	0.0350 (8)	0.0379 (8)	0.0127 (7)	0.0195 (7)	0.0095 (7)
C17	0.058 (1)	0.047 (1)	0.055 (1)	0.0170 (9)	0.0291 (9)	0.0194 (9)
C18	0.095 (2)	0.048 (1)	0.057 (1)	0.024 (1)	0.033 (1)	0.026 (1)
C19	0.080 (2)	0.048 (1)	0.053 (1)	0.028 (1)	0.004 (1)	0.0116 (9)
C20	0.051 (1)	0.052 (1)	0.068 (1)	0.0156 (9)	0.009 (1)	0.011 (1)
C21	0.048 (1)	0.045 (1)	0.055 (1)	0.0111 (8)	0.0219 (8)	0.0148 (9)

Geometric parameters (Å, º)

S1—O2	1.435 (2)	C9—C10	1.516 (3)
S1—O3	1.426 (1)	C9—H10	0.930
S1—C1	1.781 (2)	C10—C11	1.395 (2)
S1—C16	1.761 (2)	C10—C15	1.380 (2)
O1—C2	1.203 (2)	C11—C12	1.376 (3)
C1—C2	1.526 (3)	C11—H11	0.930
C1—H1	0.930	C12—C13	1.372 (3)
C1—H2	0.930	C12—H12	0.930
C2—C3	1.501 (2)	C13—C14	1.382 (3)
C3—C4	1.572 (2)	C13—H13	0.930
C3—C9	1.560 (3)	C14—C15	1.380 (3)
C3—H3	0.930	C14—H14	0.930
C4—C5	1.505 (3)	C15—H15	0.930
C4—C8	1.537 (2)	C16—C17	1.384 (3)
C4—H4	0.930	C16—C21	1.380 (3)
C5—C6	1.320 (3)	C17—C18	1.379 (3)
C5—H5	0.930	C17—H16	0.930
C6—C7	1.506 (3)	C18—C19	1.379 (4)
C6—H6	0.930	C18—H17	0.930
C7—C8	1.533 (3)	C19—C20	1.366 (4)
C7—C9	1.555 (2)	C19—H18	0.930
C7—H7	0.930	C20—C21	1.373 (3)
C8—H8	0.930	C20—H19	0.930
C8—H9	0.930	C21—H20	0.930
O2—S1—O3	119.09 (8)	C4—C8—C7	93.5 (1)
O2—S1—C1	105.24 (9)	C10—C9—H10	108.1
O2—S1—C16	108.7 (1)	C10—C9—C3	113.4 (2)
O3—S1—C1	109.31 (9)	C10—C9—C7	117.0 (1)
O3—S1—C16	108.54 (9)	H10—C9—C3	107.8
C1—S1—C16	105.11 (8)	H10—C9—C7	108.3
C2—C1—H1	107.8	C3—C9—C7	101.7 (1)
C2—C1—H2	108.0	C11—C10—C15	117.3 (2)
C2—C1—S1	115.8 (1)	C11—C10—C9	123.6 (1)
H1—C1—H2	109.5	C15—C10—C9	119.1 (1)
H1—C1—S1	107.8	C12—C11—H11	119.4
H2—C1—S1	107.9	C12—C11—C10	121.2 (2)
C3—C2—O1	124.0 (2)	H11—C11—C10	119.3
C3—C2—C1	116.8 (1)	C13—C12—H12	120.0
O1—C2—C1	119.2 (1)	C13—C12—C11	120.6 (2)
C4—C3—C9	103.3 (1)	H12—C12—C11	119.3
C4—C3—H3	109.6	C14—C13—H13	121.2
C4—C3—C2	111.8 (2)	C14—C13—C12	119.1 (2)
C9—C3—H3	108.5	H13—C13—C12	119.7
C9—C3—C2	114.8 (1)	C15—C14—H14	119.9
H3—C3—C2	108.7	C15—C14—C13	120.1 (2)
C5—C4—C8	101.2 (2)	H14—C14—C13	120.0
C5—C4—H4	116.5	H15—C15—C10	118.4
C5—C4—C3	105.5 (1)	H15—C15—C14	119.8
C8—C4—H4	116.2	C10—C15—C14	121.7 (1)
C8—C4—C3	99.2 (1)	C17—C16—C21	121.1 (2)
H4—C4—C3	115.8	C17—C16—S1	119.4 (2)
C6—C5—H5	126.0	C21—C16—S1	119.5 (2)
C6—C5—C4	107.0 (2)	C18—C17—H16	121.3
H5—C5—C4	126.9	C18—C17—C16	118.6 (2)
C7—C6—H6	125.6	H16—C17—C16	120.1
C7—C6—C5	108.4 (2)	C19—C18—H17	119.8
H6—C6—C5	126.0	C19—C18—C17	120.3 (2)
C8—C7—C9	101.1 (2)	H17—C18—C17	119.9
C8—C7—H7	116.6	C20—C19—H18	119.5
C8—C7—C6	100.6 (2)	C20—C19—C18	120.3 (2)
C9—C7—H7	115.4	H18—C19—C18	120.2
C9—C7—C6	105.5 (1)	C21—C20—H19	119.5
H7—C7—C6	115.5	C21—C20—C19	120.4 (2)
H8—C8—H9	109.5	H19—C20—C19	120.0
H8—C8—C4	113.2	H20—C21—C16	119.9
H8—C8—C7	113.2	H20—C21—C20	120.8
H9—C8—C4	114.0	C16—C21—C20	119.2 (2)
H9—C8—C7	112.9
O2—S1—C1—C2	−179.6 (1)	C1—S1—C16—C21	100.7 (1)
O3—S1—C1—C2	−50.6 (1)	S1—C1—C2—O1	67.4 (2)
C16—S1—C1—C2	65.7 (1)	S1—C1—C2—C3	−115.3 (2)
O2—S1—C16—C17	166.0 (1)	O1—C2—C3—C4	120.2 (2)
O2—S1—C16—C21	−11.6 (1)	O1—C2—C3—C9	3.0 (3)
O3—S1—C16—C17	35.2 (2)	C1—C2—C3—C4	−57.0 (2)
O3—S1—C16—C21	−142.5 (1)	C1—C2—C3—C9	−174.2 (2)
C1—S1—C16—C17	−81.7 (1)