(1R,4R,7S)-1,7-Dimethyl-7-(phenyl-sulfonyl-meth-yl)spiro-[bicyclo-[2.2.1]heptane-2,2'-1,3-dioxolane].

In the title compound, C(18)H(24)O(4)S, 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 = 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

Δρmax = 0.18 e Å−3

Δρmin = −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.

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

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

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

C18H24O4S	F000 = 720
Mr = 336.43	Dx = 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

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

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0351P)2 + 0.3259P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.036	(Δ/σ)max = 0.001
wR(F2) = 0.083	Δρmax = 0.18 e Å−3
S = 1.01	Δρmin = −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

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
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)

	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)

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)