(1R,4R,7S)-1,7-Dimethyl-7-(phenyl­sulfonyl­meth­yl)spiro­[bicyclo­[2.2.1]heptane-2,2′-1,3-dioxolane]

Ya-Wen Wang; Yu Peng

doi:10.1107/S1600536807058084

. 2007 Dec 6;64(Pt 1):o57. doi: 10.1107/S1600536807058084

(1R,4R,7S)-1,7-Dimethyl-7-(phenylsulfonylmethyl)spiro[bicyclo[2.2.1]heptane-2,2′-1,3-dioxolane]

Ya-Wen Wang ^a, Yu Peng ^a,^*

PMCID: PMC2915015 PMID: 21200933

Abstract

In the title compound, C₁₈H₂₄O₄S, the chiral bicyclo[2.2.1]heptane group is not symmetrical due to the influence of the substituents. The angle between the three-atom bridge plane and the four-atom planes of the boat-shaped six-membered ring are 55.07 (19) and 56.24 (19)°. The bridgehead angle is 92.75 (17)°.

Related literature

For related literature, see: Antczak et al. (1987 ▶); García Martínez et al. (2004 ▶); Gorichko et al. (2002 ▶); Kuo & Money (1988 ▶); Money (1985 ▶); Tanyeli et al. (2004 ▶); Trost et al. (1979 ▶); Vaillancourt & Albizati (1993 ▶). For related structures, see: Bear & Trotter (1975 ▶); Cullen et al. (1988 ▶); Komarov et al. (1997 ▶); Takasu et al. (2000 ▶).

Experimental

Crystal data

C₁₈H₂₄O₄S
M _r = 336.43
Orthorhombic,
a = 10.5420 (2) Å
b = 11.7946 (2) Å
c = 13.2997 (3) Å
V = 1653.67 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 294 (2) K
0.22 × 0.20 × 0.12 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: none
8969 measured reflections
3080 independent reflections
2595 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.083
S = 1.01
3080 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), 1307 Friedel pairs
Flack parameter: 0.09 (9)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807058084/hg2344sup1.cif

e-64-00o57-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807058084/hg2344Isup2.hkl

e-64-00o57-Isup2.hkl^{(151.2KB, hkl)}

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

Acknowledgments

We acknowledge financial support from the Research Fund for the New Faculty at the State Key Laboratory of Applied Organic Chemstry.

supplementary crystallographic information

Comment

The uniqueness of the bicyclic structure of camphor is illustrated by a wide variety of intriguing structure transformations that frequently involve fascinating rearrangement processes (Money, 1985; García Martínez et al., 2004). Studies towards these transformations have produced much chemical knowledge on theoretical and mechanistic aspects of organic chemistry in the past century and offered synthetically useful chiral building blocks (Kuo & Money, 1988; Vaillancourt & Albizati, 1993) and chiral ligands (Tanyeli et al., 2004; Gorichko et al., 2002; Komarov et al., 1997) from readily available natural camphor. Some related X-ray structures (Beta & Trotter, 1975; Cullen et al., 1988; Takasu et al., 2000; Antczak et al., 1987) have been obtained.

The chiral bicyclo[2.2.1]heptane group is not symmetrical due to the influence of the substituents. The angles between the three-atom bridge plane, C10, C13, C14 and the four-atom planes (C9, C10, C14, C18 and C10, C11, C12, C14) of the boat-shaped six-membered ring are 55.07 (19) and 56.24 (19)° while the bridgehead angle is 92.75 (17)°.

Experimental

The title compound was prepared by the reaction of sodium benzenesulfinate with (+)-8-bromocamphor (Bear & Trotter, 1975) ketal through the literature method (Trost et al., 1979). Single crystals suitable for X-ray determination were obtained by slow evaporation of a EtOAc solution over a period of several days. IR (film): 3063, 2961, 2883, 1586, 1478, 1448, 1306, 1145, 1084, 1053, 1023, 972, 742, 691 cm^-1; ¹H NMR (400 MHz, CDCl₃): 7.93 (d, J=7.2 Hz, 2H), 7.65 (t, J=8.5 Hz, 1H), 7.56 (t, J=8.0 Hz, 2H), 4.12 (d, J=14.7 Hz, 1H), 3.91–3.86 (m, 1H), 3.84–3.81(m, 1H), 3.76–3.70 (m, 2H), 2.90 (d, J=14.7 Hz, 1H), 2.11 (dt, J=3.4, 13.7 Hz, 1H), 1.94–1.89 (m, 1H), 1.77–1.75 (m, 1H), 1.52 (d, J=13.9 Hz, 1H), 1.37–1.26 (m, 3H), 1.23 (s, 3H), 0.89 (s, 3H) p.p.m.; EIMS m/z (%): 336 (M⁺, 0.6), 321 (3.3), 272 (1), 235 (1), 181 (38), 125 (3), 109 (14), 95 (100); HRMS (ESI): calcd. for C₁₈H₂₅SO₄₊ [M+H]₊: 337.1468, found: 337.1460.

Figures

Fig. 1. — The independent components of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C₁₈H₂₄O₄S	F₀₀₀ = 720
M_r = 336.43	D_x = 1.351 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2482 reflections
a = 10.5420 (2) Å	θ = 2.3–22.9º
b = 11.7946 (2) Å	µ = 0.21 mm⁻¹
c = 13.2997 (3) Å	T = 294 (2) K
V = 1653.67 (6) Å³	Block, colorless
Z = 4	0.22 × 0.20 × 0.12 mm

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Data collection

Bruker APEX CCD area-detector diffractometer	2595 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Monochromator: graphite	θ_max = 25.5º
T = 294(2) K	θ_min = 2.3º
phi and ω scans	h = −12→10
Absorption correction: none	k = −14→14
8969 measured reflections	l = −14→16
3080 independent reflections

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Refinement

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0351P)² + 0.3259P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.036	(Δ/σ)_max = 0.001
wR(F²) = 0.083	Δρ_max = 0.18 e Å⁻³
S = 1.01	Δρ_min = −0.20 e Å⁻³
3080 reflections	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
211 parameters	Extinction coefficient: 0.0024 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1307 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.09 (9)
Hydrogen site location: inferred from neighbouring sites

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Special details

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.

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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
C1	0.8521 (3)	0.4745 (2)	0.8698 (2)	0.0553 (7)
H1	0.9141	0.4185	0.8671	0.066*
C2	0.7480 (3)	0.4684 (2)	0.8078 (2)	0.0573 (8)
H2	0.7396	0.4083	0.7630	0.069*
C3	0.6567 (3)	0.5508 (2)	0.81181 (19)	0.0559 (7)
H3	0.5869	0.5464	0.7693	0.067*
C4	0.6670 (2)	0.6412 (2)	0.87884 (18)	0.0460 (6)
H4	0.6050	0.6972	0.8814	0.055*
C5	0.7711 (2)	0.64549 (17)	0.94106 (17)	0.0366 (5)
C6	0.8644 (3)	0.5640 (2)	0.93635 (18)	0.0458 (6)
H6	0.9353	0.5690	0.9777	0.055*
C7	0.9448 (3)	1.1891 (2)	1.1304 (2)	0.0520 (7)
H7A	1.0316	1.2009	1.1088	0.062*
H7B	0.9416	1.1890	1.2033	0.062*
C8	0.8581 (3)	1.2769 (2)	1.08728 (18)	0.0543 (7)
H8A	0.7817	1.2846	1.1273	0.065*
H8B	0.8999	1.3500	1.0829	0.065*
C9	0.8317 (2)	1.11268 (18)	0.99706 (16)	0.0393 (6)
C10	0.8975 (2)	1.06072 (19)	0.90376 (17)	0.0386 (6)
C11	0.8356 (3)	1.1177 (2)	0.81204 (18)	0.0526 (7)
H11A	0.8811	1.0990	0.7509	0.063*
H11B	0.8342	1.1995	0.8199	0.063*
C12	0.7000 (3)	1.0694 (2)	0.80945 (18)	0.0545 (7)
H12A	0.6838	1.0296	0.7469	0.065*
H12B	0.6373	1.1289	0.8177	0.065*
C13	0.8356 (2)	0.93875 (18)	0.89830 (16)	0.0352 (5)
C14	0.6987 (2)	0.9872 (2)	0.89958 (17)	0.0420 (6)
H14	0.6319	0.9295	0.8967	0.050*
C15	1.0411 (2)	1.0690 (2)	0.9064 (2)	0.0567 (7)
H15C	1.0757	1.0343	0.8472	0.085*
H15A	1.0726	1.0307	0.9650	0.085*
H15B	1.0657	1.1474	0.9087	0.085*
C16	0.8700 (3)	0.8742 (2)	0.80203 (17)	0.0474 (6)
H16B	0.9595	0.8591	0.8013	0.071*
H16C	0.8478	0.9192	0.7445	0.071*
H16A	0.8242	0.8039	0.8000	0.071*
C17	0.8764 (2)	0.86578 (17)	0.98851 (17)	0.0353 (5)
H17B	0.8897	0.9172	1.0444	0.042*
H17A	0.9587	0.8340	0.9719	0.042*
C18	0.6982 (2)	1.0590 (2)	0.99592 (17)	0.0440 (6)
H18B	0.6847	1.0121	1.0549	0.053*
H18A	0.6329	1.1168	0.9933	0.053*
O1	0.65482 (17)	0.79178 (14)	1.05340 (14)	0.0596 (5)
O2	0.8532 (2)	0.70566 (14)	1.11702 (12)	0.0606 (5)
O3	0.83048 (18)	1.23328 (13)	0.99050 (12)	0.0545 (5)
O4	0.89416 (16)	1.08703 (13)	1.08999 (11)	0.0438 (4)
S1	0.78162 (6)	0.75224 (5)	1.03435 (4)	0.04187 (16)

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Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0658 (19)	0.0410 (14)	0.0590 (17)	0.0034 (14)	0.0122 (16)	−0.0026 (13)
C2	0.077 (2)	0.0501 (16)	0.0452 (15)	−0.0175 (16)	0.0103 (15)	−0.0074 (12)
C3	0.0596 (18)	0.0666 (18)	0.0417 (14)	−0.0257 (17)	−0.0051 (13)	0.0071 (13)
C4	0.0445 (15)	0.0467 (14)	0.0468 (15)	−0.0053 (12)	0.0025 (12)	0.0061 (11)
C5	0.0384 (13)	0.0340 (12)	0.0375 (12)	−0.0076 (11)	0.0056 (11)	0.0016 (9)
C6	0.0477 (16)	0.0437 (13)	0.0461 (15)	−0.0036 (13)	−0.0010 (12)	−0.0001 (11)
C7	0.0631 (18)	0.0451 (14)	0.0476 (15)	−0.0054 (14)	−0.0085 (13)	−0.0096 (13)
C8	0.0682 (18)	0.0419 (15)	0.0529 (15)	0.0028 (13)	−0.0070 (14)	−0.0101 (11)
C9	0.0514 (15)	0.0297 (11)	0.0368 (12)	0.0014 (11)	−0.0056 (11)	0.0007 (9)
C10	0.0434 (14)	0.0358 (12)	0.0366 (13)	−0.0043 (11)	0.0009 (11)	0.0030 (10)
C11	0.080 (2)	0.0418 (14)	0.0361 (13)	−0.0009 (15)	−0.0051 (13)	0.0042 (11)
C12	0.067 (2)	0.0502 (15)	0.0459 (15)	0.0102 (14)	−0.0169 (14)	−0.0006 (12)
C13	0.0398 (13)	0.0350 (11)	0.0307 (11)	−0.0037 (10)	0.0021 (10)	0.0001 (10)
C14	0.0392 (14)	0.0460 (13)	0.0407 (13)	0.0013 (11)	−0.0061 (11)	−0.0040 (11)
C15	0.0490 (16)	0.0571 (17)	0.0639 (18)	−0.0137 (13)	0.0117 (14)	−0.0007 (15)
C16	0.0586 (17)	0.0426 (14)	0.0411 (14)	−0.0023 (13)	0.0081 (12)	−0.0013 (11)
C17	0.0338 (12)	0.0321 (11)	0.0400 (13)	−0.0032 (10)	0.0017 (10)	−0.0028 (9)
C18	0.0429 (15)	0.0452 (13)	0.0439 (13)	0.0074 (12)	0.0008 (11)	−0.0031 (11)
O1	0.0523 (11)	0.0550 (10)	0.0717 (12)	−0.0074 (9)	0.0261 (10)	−0.0081 (9)
O2	0.0968 (15)	0.0496 (10)	0.0354 (9)	−0.0141 (10)	−0.0086 (10)	0.0099 (8)
O3	0.0854 (13)	0.0322 (9)	0.0459 (9)	0.0029 (9)	−0.0093 (9)	−0.0005 (7)
O4	0.0614 (11)	0.0349 (9)	0.0351 (9)	−0.0056 (8)	−0.0094 (8)	−0.0003 (7)
S1	0.0523 (4)	0.0367 (3)	0.0367 (3)	−0.0066 (3)	0.0075 (3)	0.0005 (3)

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Geometric parameters (Å, °)

C1—C2	1.375 (4)	C10—C13	1.581 (3)
C1—C6	1.383 (3)	C11—C12	1.540 (4)
C1—H1	0.9300	C11—H11A	0.9700
C2—C3	1.368 (4)	C11—H11B	0.9700
C2—H2	0.9300	C12—C14	1.542 (3)
C3—C4	1.394 (4)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.375 (3)	C13—C16	1.533 (3)
C4—H4	0.9300	C13—C17	1.538 (3)
C5—C6	1.377 (3)	C13—C14	1.553 (3)
C5—S1	1.771 (2)	C14—C18	1.536 (3)
C6—H6	0.9300	C14—H14	0.9800
C7—O4	1.422 (3)	C15—H15C	0.9600
C7—C8	1.496 (3)	C15—H15A	0.9600
C7—H7A	0.9700	C15—H15B	0.9600
C7—H7B	0.9700	C16—H16B	0.9600
C8—O3	1.417 (3)	C16—H16C	0.9600
C8—H8A	0.9700	C16—H16A	0.9600
C8—H8B	0.9700	C17—S1	1.779 (2)
C9—O3	1.425 (3)	C17—H17B	0.9700
C9—O4	1.433 (3)	C17—H17A	0.9700
C9—C18	1.543 (3)	C18—H18B	0.9700
C9—C10	1.548 (3)	C18—H18A	0.9700
C10—C15	1.517 (3)	O1—S1	1.4383 (18)
C10—C11	1.538 (3)	O2—S1	1.4422 (18)

C2—C1—C6	119.9 (3)	C11—C12—H12A	111.2
C2—C1—H1	120.1	C14—C12—H12A	111.2
C6—C1—H1	120.1	C11—C12—H12B	111.2
C3—C2—C1	120.0 (2)	C14—C12—H12B	111.2
C3—C2—H2	120.0	H12A—C12—H12B	109.1
C1—C2—H2	120.0	C16—C13—C17	107.93 (18)
C2—C3—C4	120.9 (3)	C16—C13—C14	114.30 (19)
C2—C3—H3	119.5	C17—C13—C14	117.21 (19)
C4—C3—H3	119.5	C16—C13—C10	113.13 (18)
C5—C4—C3	118.3 (2)	C17—C13—C10	110.99 (18)
C5—C4—H4	120.8	C14—C13—C10	92.75 (17)
C3—C4—H4	120.8	C18—C14—C12	107.56 (18)
C4—C5—C6	121.1 (2)	C18—C14—C13	102.43 (18)
C4—C5—S1	119.86 (18)	C12—C14—C13	102.4 (2)
C6—C5—S1	118.91 (18)	C18—C14—H14	114.4
C5—C6—C1	119.7 (3)	C12—C14—H14	114.4
C5—C6—H6	120.2	C13—C14—H14	114.4
C1—C6—H6	120.2	C10—C15—H15C	109.5
O4—C7—C8	102.25 (19)	C10—C15—H15A	109.5
O4—C7—H7A	111.3	H15C—C15—H15A	109.5
C8—C7—H7A	111.3	C10—C15—H15B	109.5
O4—C7—H7B	111.3	H15C—C15—H15B	109.5
C8—C7—H7B	111.3	H15A—C15—H15B	109.5
H7A—C7—H7B	109.2	C13—C16—H16B	109.5
O3—C8—C7	102.85 (19)	C13—C16—H16C	109.5
O3—C8—H8A	111.2	H16B—C16—H16C	109.5
C7—C8—H8A	111.2	C13—C16—H16A	109.5
O3—C8—H8B	111.2	H16B—C16—H16A	109.5
C7—C8—H8B	111.2	H16C—C16—H16A	109.5
H8A—C8—H8B	109.1	C13—C17—S1	122.12 (16)
O3—C9—O4	105.53 (17)	C13—C17—H17B	106.8
O3—C9—C18	113.6 (2)	S1—C17—H17B	106.8
O4—C9—C18	109.93 (18)	C13—C17—H17A	106.8
O3—C9—C10	110.50 (18)	S1—C17—H17A	106.8
O4—C9—C10	113.71 (18)	H17B—C17—H17A	106.6
C18—C9—C10	103.77 (18)	C14—C18—C9	103.38 (19)
C15—C10—C11	114.4 (2)	C14—C18—H18B	111.1
C15—C10—C9	113.7 (2)	C9—C18—H18B	111.1
C11—C10—C9	105.84 (19)	C14—C18—H18A	111.1
C15—C10—C13	118.1 (2)	C9—C18—H18A	111.1
C11—C10—C13	100.76 (18)	H18B—C18—H18A	109.1
C9—C10—C13	102.27 (17)	C8—O3—C9	107.78 (17)
C10—C11—C12	104.44 (19)	C7—O4—C9	108.65 (17)
C10—C11—H11A	110.9	O1—S1—O2	118.38 (12)
C12—C11—H11A	110.9	O1—S1—C5	107.19 (11)
C10—C11—H11B	110.9	O2—S1—C5	107.22 (10)
C12—C11—H11B	110.9	O1—S1—C17	109.78 (11)
H11A—C11—H11B	108.9	O2—S1—C17	104.73 (11)
C11—C12—C14	102.9 (2)	C5—S1—C17	109.29 (10)

C6—C1—C2—C3	0.0 (4)	C11—C12—C14—C13	−35.5 (2)
C1—C2—C3—C4	−0.4 (4)	C16—C13—C14—C18	−172.69 (19)
C2—C3—C4—C5	−0.1 (4)	C17—C13—C14—C18	59.6 (2)
C3—C4—C5—C6	1.2 (3)	C10—C13—C14—C18	−55.74 (19)
C3—C4—C5—S1	−174.85 (17)	C16—C13—C14—C12	−61.3 (2)
C4—C5—C6—C1	−1.7 (4)	C17—C13—C14—C12	170.99 (18)
S1—C5—C6—C1	174.40 (19)	C10—C13—C14—C12	55.66 (19)
C2—C1—C6—C5	1.1 (4)	C16—C13—C17—S1	−81.5 (2)
O4—C7—C8—O3	−35.5 (3)	C14—C13—C17—S1	49.2 (3)
O3—C9—C10—C15	76.8 (2)	C10—C13—C17—S1	153.97 (16)
O4—C9—C10—C15	−41.6 (3)	C12—C14—C18—C9	−69.3 (2)
C18—C9—C10—C15	−161.0 (2)	C13—C14—C18—C9	38.2 (2)
O3—C9—C10—C11	−49.6 (2)	O3—C9—C18—C14	117.2 (2)
O4—C9—C10—C11	−168.02 (19)	O4—C9—C18—C14	−124.85 (18)
C18—C9—C10—C11	72.6 (2)	C10—C9—C18—C14	−2.9 (2)
O3—C9—C10—C13	−154.66 (19)	C7—C8—O3—C9	31.9 (3)
O4—C9—C10—C13	86.9 (2)	O4—C9—O3—C8	−15.7 (3)
C18—C9—C10—C13	−32.5 (2)	C18—C9—O3—C8	104.8 (2)
C15—C10—C11—C12	164.0 (2)	C10—C9—O3—C8	−139.0 (2)
C9—C10—C11—C12	−69.9 (2)	C8—C7—O4—C9	26.9 (3)
C13—C10—C11—C12	36.2 (2)	O3—C9—O4—C7	−8.1 (2)
C10—C11—C12—C14	−1.0 (3)	C18—C9—O4—C7	−131.0 (2)
C15—C10—C13—C16	−62.9 (3)	C10—C9—O4—C7	113.2 (2)
C11—C10—C13—C16	62.4 (2)	C4—C5—S1—O1	21.5 (2)
C9—C10—C13—C16	171.40 (19)	C6—C5—S1—O1	−154.61 (18)
C15—C10—C13—C17	58.6 (3)	C4—C5—S1—O2	149.62 (19)
C11—C10—C13—C17	−176.12 (19)	C6—C5—S1—O2	−26.5 (2)
C9—C10—C13—C17	−67.1 (2)	C4—C5—S1—C17	−97.4 (2)
C15—C10—C13—C14	179.1 (2)	C6—C5—S1—C17	86.5 (2)
C11—C10—C13—C14	−55.55 (19)	C13—C17—S1—O1	−52.6 (2)
C9—C10—C13—C14	53.46 (19)	C13—C17—S1—O2	179.28 (18)
C11—C12—C14—C18	72.0 (2)	C13—C17—S1—C5	64.7 (2)

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2344).

References

Antczak, K., Kingston, J. F. & Fallis, A. G. (1987). Can. J. Chem.65, 114–123.
Bear, C. A. & Trotter, J. (1975). Acta Cryst. B31, 903–904.
Bruker (2000). SAINT (Version 6.12), SMART (Version 5.050), and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.
Cullen, W. R., Rettig, S. J., Trotter, J. & Wickenheisher, E. B. (1988). Can. J. Chem.66, 2007–2013.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
García Martínez, A., Teso Vilar, E., García Fraile, A., de la Moya Cerero, S., Diaz Morillo, C. & Pérez Morillo, R. (2004). J. Org. Chem.69, 7348–7351.
Gorichko, M. V., Grygorenko, O. O. & Komarov, I. V. (2002). Tetrahedron Lett.43, 9411–9412.
Komarov, I. V., Gorichko, M. V. & Komilov, M. Y. (1997). Tetrahedron Asymmetry, 8, 435–445.
Kuo, D. L. & Money, T. (1988). Can. J. Chem.66, 1794–1804.
Money, T. (1985). Nat. Prod. Rep.2, 253–289. [DOI] [PubMed]
Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
Takasu, K., Mizutani, S., Noguchi, M., Makita, K. & Ihara, M. (2000). J. Org. Chem.65, 4112–4119. [DOI] [PubMed]
Tanyeli, C., Akhmedov, I. M. & Işık, M. (2004). Tetrahedron Lett.45, 5799–5801.
Trost, B. M., Bernstein, P. R. & Funfschilling, P. C. (1979). J. Am. Chem. Soc.101, 4378–4980.
Vaillancourt, V. & Albizati, K. F. (1993). J. Am. Chem. Soc.115, 3499–1502.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807058084/hg2344sup1.cif

e-64-00o57-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807058084/hg2344Isup2.hkl

e-64-00o57-Isup2.hkl^{(151.2KB, hkl)}

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

[bb1] Antczak, K., Kingston, J. F. & Fallis, A. G. (1987). Can. J. Chem.65, 114–123.

[bb2] Bear, C. A. & Trotter, J. (1975). Acta Cryst. B31, 903–904.

[bb3] Bruker (2000). SAINT (Version 6.12), SMART (Version 5.050), and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.

[bb4] Cullen, W. R., Rettig, S. J., Trotter, J. & Wickenheisher, E. B. (1988). Can. J. Chem.66, 2007–2013.

[bb16] Flack, H. D. (1983). Acta Cryst. A39, 876–881.

[bb5] García Martínez, A., Teso Vilar, E., García Fraile, A., de la Moya Cerero, S., Diaz Morillo, C. & Pérez Morillo, R. (2004). J. Org. Chem.69, 7348–7351.

[bb6] Gorichko, M. V., Grygorenko, O. O. & Komarov, I. V. (2002). Tetrahedron Lett.43, 9411–9412.

[bb7] Komarov, I. V., Gorichko, M. V. & Komilov, M. Y. (1997). Tetrahedron Asymmetry, 8, 435–445.

[bb8] Kuo, D. L. & Money, T. (1988). Can. J. Chem.66, 1794–1804.

[bb9] Money, T. (1985). Nat. Prod. Rep.2, 253–289. [DOI] [PubMed]

[bb10] Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473.

[bb11] Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.

[bb12] Takasu, K., Mizutani, S., Noguchi, M., Makita, K. & Ihara, M. (2000). J. Org. Chem.65, 4112–4119. [DOI] [PubMed]

[bb13] Tanyeli, C., Akhmedov, I. M. & Işık, M. (2004). Tetrahedron Lett.45, 5799–5801.

[bb14] Trost, B. M., Bernstein, P. R. & Funfschilling, P. C. (1979). J. Am. Chem. Soc.101, 4378–4980.

[bb15] Vaillancourt, V. & Albizati, K. F. (1993). J. Am. Chem. Soc.115, 3499–1502.

PERMALINK

(1R,4R,7S)-1,7-Dimethyl-7-(phenylsulfonylmethyl)spiro[bicyclo[2.2.1]heptane-2,2′-1,3-dioxolane]

Ya-Wen Wang

Yu Peng

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(1R,4R,7S)-1,7-Dimethyl-7-(phenyl­sulfonyl­meth­yl)spiro­[bicyclo­[2.2.1]heptane-2,2′-1,3-dioxolane]

Ya-Wen Wang

Yu Peng

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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Geometric parameters (Å, °)

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(1R,4R,7S)-1,7-Dimethyl-7-(phenylsulfonylmethyl)spiro[bicyclo[2.2.1]heptane-2,2′-1,3-dioxolane]

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)