(1R,2R,4S,5S)-1,2,4,8,8-Penta­methyl-3-thiabicyclo­[3.2.1]octane 3,3-dioxide

The title compound, C₁₂H₂₂O₂S, contains four chiral C atoms, which have been assigned. There are inter­molecular C—H...O inter­actions in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.087
• Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A    ..  O2      ..       2.62 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.28
           From the CIF: _reflns_number_total               2981
           Count of symmetry unique reflns         1778
           Completeness (_total/calc)            167.66%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1203
           Fraction of Friedel pairs measured     0.677
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

(1R,2R,4S,5S)-1,2,4,8,8-pentamethyl-3-thiabicyclo[3.2.1]octane 3,3-dioxide

Crystal data

C12H22O2S	Dx = 1.232 Mg m^−3
Mr = 230.36	Melting point: 374.2 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3357 reflections
a = 7.9967 (6) Å	θ = 2.4–27.3°
b = 10.6591 (8) Å	µ = 0.24 mm^−1
c = 14.5696 (10) Å	T = 293 K
V = 1241.88 (16) Å^3	Block, colorless
Z = 4	0.32 × 0.26 × 0.26 mm
F(000) = 504

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2981 independent reflections
Radiation source: fine-focus sealed tube	2530 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→7
Tmin = 0.93, Tmax = 0.94	k = −13→14
7787 measured reflections	l = −19→19

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.048P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.087	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.25 e Å^−3
2981 reflections	Δρmin = −0.17 e Å^−3
142 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.132 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.03 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2135 (2)	0.47098 (14)	0.54548 (10)	0.0401 (4)
C2	0.0917 (2)	0.58297 (14)	0.53401 (10)	0.0416 (3)
H2	0.1532	0.6583	0.5527	0.050*
C3	−0.0176 (2)	0.50733 (17)	0.71181 (11)	0.0459 (4)
H3	0.0358	0.5748	0.7469	0.055*
C4	0.1153 (2)	0.40750 (15)	0.69377 (11)	0.0431 (4)
H4	0.1467	0.3685	0.7522	0.052*
C5	0.0579 (3)	0.30437 (16)	0.62680 (13)	0.0553 (5)
H5A	0.1052	0.2239	0.6440	0.066*
H5B	−0.0630	0.2974	0.6269	0.066*
C6	0.1211 (3)	0.34441 (15)	0.53148 (12)	0.0522 (5)
H6A	0.0281	0.3547	0.4894	0.063*
H6B	0.1967	0.2818	0.5067	0.063*
C7	0.2738 (2)	0.45953 (15)	0.64728 (10)	0.0402 (4)
C8	0.4132 (3)	0.36038 (19)	0.65725 (13)	0.0609 (5)
H8A	0.5154	0.3926	0.6319	0.091*
H8B	0.3816	0.2855	0.6250	0.091*
H8C	0.4294	0.3413	0.7210	0.091*
C9	0.3436 (2)	0.58064 (18)	0.68883 (12)	0.0534 (4)
H9A	0.3648	0.5682	0.7530	0.080*
H9B	0.2637	0.6471	0.6811	0.080*
H9C	0.4459	0.6026	0.6584	0.080*
C10	0.3572 (2)	0.4894 (2)	0.47655 (12)	0.0606 (5)
H10A	0.3157	0.4781	0.4153	0.091*
H10B	0.4436	0.4291	0.4885	0.091*
H10C	0.4018	0.5726	0.4828	0.091*
C11	0.0290 (3)	0.6068 (2)	0.43614 (12)	0.0625 (5)
H11A	0.1201	0.6356	0.3987	0.094*
H11B	−0.0572	0.6694	0.4373	0.094*
H11C	−0.0150	0.5303	0.4111	0.094*
C12	−0.1667 (2)	0.4612 (2)	0.76782 (13)	0.0693 (6)
H12A	−0.2177	0.3913	0.7372	0.104*
H12B	−0.2469	0.5277	0.7740	0.104*
H12C	−0.1294	0.4356	0.8276	0.104*
O1	−0.1465 (2)	0.70070 (15)	0.62453 (12)	0.0811 (5)
O2	−0.21053 (16)	0.49101 (16)	0.56484 (9)	0.0688 (4)
S1	−0.09118 (6)	0.57445 (4)	0.60622 (3)	0.04958 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0422 (8)	0.0399 (8)	0.0383 (8)	−0.0004 (7)	0.0037 (7)	−0.0023 (6)
C2	0.0434 (8)	0.0409 (8)	0.0405 (7)	−0.0036 (8)	−0.0013 (7)	0.0020 (6)
C3	0.0370 (8)	0.0610 (11)	0.0398 (8)	−0.0023 (8)	0.0030 (7)	−0.0018 (7)
C4	0.0448 (9)	0.0445 (9)	0.0401 (7)	−0.0043 (8)	−0.0001 (7)	0.0056 (6)
C5	0.0623 (12)	0.0400 (8)	0.0638 (11)	−0.0104 (8)	0.0009 (9)	0.0005 (8)
C6	0.0644 (12)	0.0413 (9)	0.0508 (9)	−0.0045 (9)	−0.0006 (9)	−0.0116 (7)
C7	0.0368 (8)	0.0442 (9)	0.0395 (8)	0.0003 (7)	0.0012 (7)	0.0014 (6)
C8	0.0498 (10)	0.0707 (12)	0.0620 (11)	0.0157 (10)	0.0033 (10)	0.0094 (9)
C9	0.0468 (9)	0.0632 (11)	0.0500 (9)	−0.0141 (9)	−0.0070 (8)	−0.0015 (9)
C10	0.0559 (11)	0.0771 (13)	0.0488 (9)	0.0046 (10)	0.0150 (8)	0.0020 (9)
C11	0.0628 (12)	0.0767 (13)	0.0479 (9)	−0.0033 (10)	−0.0073 (9)	0.0167 (9)
C12	0.0487 (11)	0.1062 (18)	0.0530 (10)	−0.0087 (12)	0.0115 (9)	0.0044 (11)
O1	0.0828 (11)	0.0750 (10)	0.0854 (10)	0.0382 (9)	0.0066 (9)	−0.0007 (8)
O2	0.0388 (7)	0.1035 (11)	0.0641 (7)	−0.0131 (8)	−0.0084 (6)	0.0057 (7)
S1	0.0400 (2)	0.0594 (3)	0.0493 (2)	0.0077 (2)	0.0004 (2)	0.00021 (19)

Geometric parameters (Å, º)

C1—C10	1.538 (2)	C7—C9	1.531 (2)
C1—C2	1.550 (2)	C7—C8	1.543 (2)
C1—C6	1.552 (2)	C8—H8A	0.9600
C1—C7	1.564 (2)	C8—H8B	0.9600
C2—C11	1.533 (2)	C8—H8C	0.9600
C2—S1	1.804 (2)	C9—H9A	0.9600
C2—H2	0.9800	C9—H9B	0.9600
C3—C12	1.526 (2)	C9—H9C	0.9600
C3—C4	1.527 (2)	C10—H10A	0.9600
C3—S1	1.796 (2)	C10—H10B	0.9600
C3—H3	0.9800	C10—H10C	0.9600
C4—C5	1.540 (2)	C11—H11A	0.9600
C4—C7	1.541 (2)	C11—H11B	0.9600
C4—H4	0.9800	C11—H11C	0.9600
C5—C6	1.538 (3)	C12—H12A	0.9600
C5—H5A	0.9700	C12—H12B	0.9600
C5—H5B	0.9700	C12—H12C	0.9600
C6—H6A	0.9700	O1—S1	1.441 (2)
C6—H6B	0.9700	O2—S1	1.437 (2)
C10—C1—C2	107.5 (1)	C9—C7—C1	114.9 (1)
C10—C1—C6	112.4 (1)	C4—C7—C1	101.0 (1)
C2—C1—C6	110.9 (1)	C8—C7—C1	111.4 (1)
C10—C1—C7	113.5 (1)	C7—C8—H8A	109.5
C2—C1—C7	110.9 (1)	C7—C8—H8B	109.5
C6—C1—C7	101.8 (1)	H8A—C8—H8B	109.5
C11—C2—C1	115.7 (1)	C7—C8—H8C	109.5
C11—C2—S1	106.6 (1)	H8A—C8—H8C	109.5
C1—C2—S1	114.1 (1)	H8B—C8—H8C	109.5
C11—C2—H2	106.6	C7—C9—H9A	109.5
C1—C2—H2	106.6	C7—C9—H9B	109.5
S1—C2—H2	106.6	H9A—C9—H9B	109.5
C12—C3—C4	114.3 (1)	C7—C9—H9C	109.5
C12—C3—S1	109.3 (1)	H9A—C9—H9C	109.5
C4—C3—S1	111.0 (1)	H9B—C9—H9C	109.5
C12—C3—H3	107.3	C1—C10—H10A	109.5
C4—C3—H3	107.3	C1—C10—H10B	109.5
S1—C3—H3	107.3	H10A—C10—H10B	109.5
C3—C4—C5	113.5 (1)	C1—C10—H10C	109.5
C3—C4—C7	113.4 (1)	H10A—C10—H10C	109.5
C5—C4—C7	102.9 (1)	H10B—C10—H10C	109.5
C3—C4—H4	108.9	C2—C11—H11A	109.5
C5—C4—H4	108.9	C2—C11—H11B	109.5
C7—C4—H4	108.9	H11A—C11—H11B	109.5
C6—C5—C4	106.0 (1)	C2—C11—H11C	109.5
C6—C5—H5A	110.5	H11A—C11—H11C	109.5
C4—C5—H5A	110.5	H11B—C11—H11C	109.5
C6—C5—H5B	110.5	C3—C12—H12A	109.5
C4—C5—H5B	110.5	C3—C12—H12B	109.5
H5A—C5—H5B	108.7	H12A—C12—H12B	109.5
C5—C6—C1	106.2 (1)	C3—C12—H12C	109.5
C5—C6—H6A	110.5	H12A—C12—H12C	109.5
C1—C6—H6A	110.5	H12B—C12—H12C	109.5
C5—C6—H6B	110.5	O2—S1—O1	116.9 (1)
C1—C6—H6B	110.5	O2—S1—C3	109.3 (1)
H6A—C6—H6B	108.7	O1—S1—C3	108.3 (1)
C9—C7—C4	115.4 (1)	O2—S1—C2	109.0 (1)
C9—C7—C8	106.1 (1)	O1—S1—C2	108.0 (1)
C4—C7—C8	107.8 (1)	C3—S1—C2	104.7 (1)
C10—C1—C2—C11	53.2 (2)	C10—C1—C7—C9	69.6 (2)
C6—C1—C2—C11	−70.0 (2)	C2—C1—C7—C9	−51.5 (2)
C7—C1—C2—C11	177.8 (2)	C6—C1—C7—C9	−169.4 (1)
C10—C1—C2—S1	177.4 (1)	C10—C1—C7—C4	−165.4 (1)
C6—C1—C2—S1	54.2 (1)	C2—C1—C7—C4	73.5 (2)
C7—C1—C2—S1	−58.0 (1)	C6—C1—C7—C4	−44.4 (2)
C12—C3—C4—C5	69.8 (2)	C10—C1—C7—C8	−51.1 (2)
S1—C3—C4—C5	−54.3 (2)	C2—C1—C7—C8	−172.2 (1)
C12—C3—C4—C7	−173.1 (1)	C6—C1—C7—C8	69.9 (2)
S1—C3—C4—C7	62.7 (2)	C12—C3—S1—O2	−47.4 (2)
C3—C4—C5—C6	95.3 (2)	C4—C3—S1—O2	79.6 (1)
C7—C4—C5—C6	−27.8 (2)	C12—C3—S1—O1	80.9 (2)
C4—C5—C6—C1	−0.3 (2)	C4—C3—S1—O1	−152.1 (1)
C10—C1—C6—C5	149.3 (2)	C12—C3—S1—C2	−164.0 (1)
C2—C1—C6—C5	−90.3 (2)	C4—C3—S1—C2	−37.0 (1)
C7—C1—C6—C5	27.6 (2)	C11—C2—S1—O2	48.7 (2)
C3—C4—C7—C9	46.3 (2)	C1—C2—S1—O2	−80.2 (1)
C5—C4—C7—C9	169.3 (1)	C11—C2—S1—O1	−79.2 (1)
C3—C4—C7—C8	164.7 (1)	C1—C2—S1—O1	151.9 (1)
C5—C4—C7—C8	−72.3 (2)	C11—C2—S1—C3	165.6 (1)
C3—C4—C7—C1	−78.4 (2)	C1—C2—S1—C3	36.6 (1)
C5—C4—C7—C1	44.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^i	0.98	2.53	3.454 (2)	156
C8—H8A···O2^ii	0.96	2.62	3.578 (2)	177
C11—H11A···O1^iii	0.96	2.58	3.424 (3)	147

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) x+1, y, z; (iii) x+1/2, −y+3/2, −z+1.