(1RS,2RS,6SR,8SR)-2-Methyl-8-(phenyl­sulfonyl)­bi­cyclo­[4.2.0]­octan-1-ol

The title compound, C₁₅H₂₀O₃S, shows a conformational arrangement of the phenyl ring that permits hydrogen-bonded dimers to be disposed about a centre of symmetry.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.053
• wR factor = 0.174
• Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.15 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C4
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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

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

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Computing details

Data collection: MSC/AFC-7 Diffractometer Control Software for Windows (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC-7 Diffractometer Control Software for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON.

(1RS,2RS,6SR,8SR)-2-Methyl-8-(phenylsulfonyl)bicyclo[4.2.0]octan-1-ol

Crystal data

C15H20O3S	F(000) = 600
Mr = 280.38	Dx = 1.217 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 24 reflections
a = 12.328 (6) Å	θ = 12.8–16.0°
b = 10.362 (4) Å	µ = 0.21 mm^−1
c = 12.149 (2) Å	T = 295 K
β = 99.60 (3)°	Prismatic, colorless
V = 1530.2 (10) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Rigaku AFC7R diffractometer	Rint = 0.067
Radiation source: Rigaku rotating anode	θmax = 27.5°, θmin = 2.6°
Graphite monochromator	h = −7→16
ω–2θ scans	k = 0→13
3987 measured reflections	l = −15→15
3516 independent reflections	3 standard reflections every 150 reflections
1717 reflections with I > 2σ(I)	intensity decay: 0.04%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.174	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0801P)^2] where P = (Fo^2 + 2Fc^2)/3
3516 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Experimental. The scan width was (1.73 + 0.30tanθ)° with an ω scan speed of 32° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S1	1.00472 (7)	0.23346 (7)	0.97401 (7)	0.0400 (2)
O1	0.80786 (18)	0.4144 (2)	1.00962 (19)	0.0547 (8)
O2	1.04527 (19)	0.3640 (2)	0.98511 (19)	0.0524 (8)
O3	1.08393 (18)	0.1299 (2)	0.98802 (18)	0.0511 (8)
C1	0.8366 (3)	0.3199 (3)	1.0922 (3)	0.0476 (11)
C2	0.7296 (3)	0.2644 (4)	1.1213 (4)	0.0712 (16)
C3	0.6894 (5)	0.3539 (6)	1.2090 (6)	0.116 (3)
C4	0.7761 (6)	0.3549 (7)	1.3144 (5)	0.129 (3)
C5	0.8815 (5)	0.4138 (5)	1.2966 (4)	0.103 (2)
C6	0.9210 (3)	0.3577 (3)	1.1938 (3)	0.0587 (11)
C7	0.9729 (3)	0.2230 (3)	1.1925 (3)	0.0563 (11)
C8	0.9148 (3)	0.2058 (3)	1.0704 (3)	0.0430 (10)
C9	0.9238 (3)	0.2163 (3)	0.8407 (3)	0.0413 (9)
C10	0.8915 (3)	0.3247 (3)	0.7759 (3)	0.0587 (12)
C11	0.8317 (4)	0.3078 (4)	0.6704 (3)	0.0731 (16)
C12	0.8065 (3)	0.1852 (4)	0.6301 (3)	0.0702 (14)
C13	0.8379 (3)	0.0796 (4)	0.6946 (3)	0.0663 (14)
C14	0.8958 (3)	0.0948 (3)	0.8007 (3)	0.0554 (11)
C21	0.6449 (4)	0.2387 (5)	1.0187 (5)	0.108 (3)
H1	0.87170	0.46700	1.00580	0.0630*
H2	0.74700	0.18380	1.15730	0.0800*
H6	0.96960	0.41890	1.17210	0.0710*
H8	0.87530	0.12580	1.05740	0.0510*
H10	0.91070	0.40880	0.80540	0.0680*
H11	0.80990	0.38130	0.62490	0.0870*
H12	0.76660	0.17440	0.55630	0.0850*
H13	0.82010	−0.00420	0.66690	0.0830*
H14	0.91850	0.02200	0.84640	0.0660*
H31	0.62110	0.32260	1.22240	0.1410*
H32	0.67940	0.43830	1.17610	0.1410*
H41	0.74620	0.40770	1.36720	0.1590*
H42	0.78600	0.27090	1.34050	0.1590*
H51	0.93270	0.39250	1.36000	0.1370*
H52	0.87120	0.50130	1.28710	0.1370*
H71	0.95100	0.16360	1.24440	0.0670*
H72	1.05120	0.22430	1.20140	0.0670*
H211	0.62360	0.31940	0.98370	0.1300*
H212	0.58200	0.20020	1.04180	0.1300*
H213	0.67440	0.18440	0.97040	0.1300*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0431 (4)	0.0344 (4)	0.0418 (4)	−0.0008 (4)	0.0054 (3)	−0.0012 (3)
O1	0.0469 (13)	0.0493 (13)	0.0682 (15)	0.0036 (10)	0.0103 (11)	0.0194 (11)
O2	0.0601 (14)	0.0368 (11)	0.0593 (14)	−0.0112 (11)	0.0072 (11)	−0.0022 (10)
O3	0.0543 (13)	0.0465 (13)	0.0516 (13)	0.0117 (10)	0.0063 (11)	−0.0010 (10)
C1	0.0523 (19)	0.0433 (17)	0.0488 (19)	0.0045 (15)	0.0129 (15)	0.0104 (15)
C2	0.061 (2)	0.073 (3)	0.085 (3)	−0.002 (2)	0.028 (2)	0.024 (2)
C3	0.097 (4)	0.141 (5)	0.132 (5)	0.027 (4)	0.080 (4)	0.035 (4)
C4	0.152 (6)	0.155 (6)	0.099 (4)	0.025 (5)	0.072 (4)	−0.004 (4)
C5	0.137 (5)	0.113 (4)	0.065 (3)	0.047 (4)	0.030 (3)	−0.014 (3)
C6	0.075 (2)	0.0494 (19)	0.051 (2)	0.0091 (18)	0.0088 (18)	−0.0076 (16)
C7	0.072 (2)	0.054 (2)	0.0425 (18)	0.0084 (19)	0.0082 (16)	0.0074 (15)
C8	0.0528 (19)	0.0327 (16)	0.0440 (17)	−0.0021 (14)	0.0095 (14)	0.0044 (12)
C9	0.0430 (16)	0.0415 (17)	0.0394 (16)	−0.0021 (14)	0.0069 (13)	0.0003 (13)
C10	0.070 (2)	0.048 (2)	0.055 (2)	−0.0039 (18)	0.0013 (18)	0.0117 (16)
C11	0.081 (3)	0.073 (3)	0.058 (2)	0.004 (2)	−0.010 (2)	0.022 (2)
C12	0.067 (2)	0.090 (3)	0.048 (2)	−0.005 (2)	−0.0070 (19)	−0.002 (2)
C13	0.078 (3)	0.061 (2)	0.053 (2)	−0.007 (2)	−0.0093 (19)	−0.0077 (18)
C14	0.069 (2)	0.0422 (18)	0.052 (2)	−0.0014 (17)	0.0010 (17)	−0.0034 (15)
C21	0.057 (3)	0.130 (5)	0.136 (5)	−0.025 (3)	0.013 (3)	0.039 (4)

Geometric parameters (Å, º)

S1—O2	1.441 (2)	C13—C14	1.374 (5)
S1—O3	1.442 (2)	C2—H2	0.9505
S1—C8	1.765 (4)	C3—H31	0.9415
S1—C9	1.764 (4)	C3—H32	0.9609
O1—C1	1.404 (4)	C4—H41	0.9621
O1—H1	0.9648	C4—H42	0.9274
C1—C2	1.533 (5)	C5—H51	0.9371
C1—C8	1.576 (5)	C5—H52	0.9201
C1—C6	1.527 (5)	C6—H6	0.9398
C2—C21	1.510 (7)	C7—H71	0.9519
C2—C3	1.555 (8)	C7—H72	0.9533
C3—C4	1.525 (10)	C8—H8	0.9610
C4—C5	1.484 (10)	C10—H10	0.9569
C5—C6	1.529 (6)	C11—H11	0.9530
C6—C7	1.537 (5)	C12—H12	0.9546
C7—C8	1.546 (5)	C13—H13	0.9438
C9—C14	1.373 (5)	C14—H14	0.9507
C9—C10	1.391 (5)	C21—H211	0.9549
C10—C11	1.379 (5)	C21—H212	0.9549
C11—C12	1.378 (6)	C21—H213	0.9297
C12—C13	1.364 (6)
S1···H1	2.9842	H1···H6	2.2302
S1···H6	3.1653	H1···O2^ii	2.0221
O1···O2	3.036 (4)	H2···C7	2.7760
O1···C9	3.383 (4)	H2···H8	2.2307
O1···C10	3.312 (5)	H2···H42	2.3754
O1···C13^i	3.291 (5)	H2···H71	2.5692
O1···O2^ii	2.918 (3)	H2···H52^vii	2.5464
O2···C6	3.174 (5)	H6···S1	3.1653
O2···O1^ii	2.918 (3)	H6···O2	2.6573
O2···O2^ii	3.075 (3)	H6···H1	2.2302
O2···O1	3.036 (4)	H6···H10^ii	2.3033
O1···H213	2.8901	H8···C21	3.0351
O1···H12^i	2.9150	H8···H2	2.2307
O1···H211	2.4474	H8···H213	2.5975
O1···H13^i	2.5828	H8···O3^iv	2.7694
O1···H32	2.7800	H10···O2	2.5547
O2···H10	2.5547	H10···H6^ii	2.3033
O2···H1	2.4414	H12···O1^vi	2.9150
O2···H6	2.6573	H12···O2^viii	2.7503
O2···H1^ii	2.0221	H13···O1^vi	2.5828
O2···H12^iii	2.7503	H14···O3	2.6831
O3···H14	2.6831	H14···O3^iv	2.5583
O3···H72	2.8616	H14···C7^iv	2.9448
O3···H8^iv	2.7694	H31···H212	2.5104
O3···H14^iv	2.5583	H31···C9^ix	3.0513
O3···H41^v	2.6996	H32···O1	2.7800
C6···O2	3.174 (5)	H32···C6	3.0661
C9···O1	3.383 (4)	H41···O3^ix	2.6996
C10···O1	3.312 (5)	H42···H2	2.3754
C13···O1^vi	3.291 (5)	H52···H2^x	2.5464
C2···H71	3.0685	H71···C2	3.0685
C6···H32	3.0661	H71···H2	2.5692
C7···H14^iv	2.9448	H72···O3	2.8616
C7···H2	2.7760	H211···O1	2.4474
C8···H213	3.0179	H212···H31	2.5104
C9···H31^v	3.0513	H213···O1	2.8901
C21···H8	3.0351	H213···C8	3.0179
H1···S1	2.9842	H213···H8	2.5975
H1···O2	2.4414
O2—S1—O3	118.05 (14)	C4—C3—H32	111.49
O2—S1—C8	109.69 (15)	H31—C3—H32	109.21
O2—S1—C9	108.36 (15)	C3—C4—H41	105.72
O3—S1—C8	106.78 (15)	C3—C4—H42	108.33
O3—S1—C9	107.55 (15)	C5—C4—H41	107.79
C8—S1—C9	105.74 (18)	C5—C4—H42	111.55
C1—O1—H1	108.52	H41—C4—H42	110.42
O1—C1—C2	107.6 (3)	C4—C5—H51	105.64
O1—C1—C6	117.1 (3)	C4—C5—H52	108.53
C2—C1—C6	114.0 (3)	C6—C5—H51	108.62
C2—C1—C8	109.3 (3)	C6—C5—H52	109.16
O1—C1—C8	119.4 (3)	H51—C5—H52	113.27
C6—C1—C8	88.6 (3)	C1—C6—H6	109.07
C1—C2—C21	112.3 (4)	C5—C6—H6	106.10
C3—C2—C21	114.5 (4)	C7—C6—H6	108.91
C1—C2—C3	108.6 (4)	C6—C7—H71	114.58
C2—C3—C4	108.7 (5)	C6—C7—H72	113.67
C3—C4—C5	112.9 (5)	C8—C7—H71	115.07
C4—C5—C6	111.6 (4)	C8—C7—H72	114.12
C1—C6—C7	89.3 (3)	H71—C7—H72	109.13
C5—C6—C7	122.9 (3)	S1—C8—H8	112.84
C1—C6—C5	119.4 (4)	C1—C8—H8	111.56
C6—C7—C8	89.3 (3)	C7—C8—H8	113.46
S1—C8—C1	117.3 (2)	C9—C10—H10	119.59
C1—C8—C7	87.2 (3)	C11—C10—H10	121.62
S1—C8—C7	112.1 (3)	C10—C11—H11	119.53
S1—C9—C10	120.2 (3)	C12—C11—H11	120.37
C10—C9—C14	120.6 (3)	C11—C12—H12	119.48
S1—C9—C14	119.2 (3)	C13—C12—H12	119.87
C9—C10—C11	118.8 (3)	C12—C13—H13	120.43
C10—C11—C12	120.1 (4)	C14—C13—H13	119.56
C11—C12—C13	120.7 (3)	C9—C14—H14	119.26
C12—C13—C14	120.0 (4)	C13—C14—H14	120.87
C9—C14—C13	119.8 (3)	C2—C21—H211	108.30
C1—C2—H2	107.39	C2—C21—H212	108.34
C3—C2—H2	106.38	C2—C21—H213	109.77
C21—C2—H2	107.26	H211—C21—H212	108.68
C2—C3—H31	108.03	H211—C21—H213	110.88
C2—C3—H32	106.93	H212—C21—H213	110.79
C4—C3—H31	112.27
O2—S1—C8—C1	37.6 (3)	C2—C1—C6—C7	92.7 (3)
O2—S1—C8—C7	−61.0 (3)	C8—C1—C6—C5	−146.0 (3)
O3—S1—C8—C1	166.6 (2)	O1—C1—C6—C7	−140.6 (3)
O3—S1—C8—C7	68.0 (2)	C8—C1—C2—C21	−87.5 (4)
C9—S1—C8—C1	−79.0 (3)	O1—C1—C6—C5	91.3 (4)
C9—S1—C8—C7	−177.7 (2)	C2—C1—C6—C5	−35.4 (4)
O2—S1—C9—C10	−12.3 (4)	C21—C2—C3—C4	171.6 (5)
O2—S1—C9—C14	165.9 (3)	C1—C2—C3—C4	−62.1 (6)
O3—S1—C9—C10	−141.0 (3)	C2—C3—C4—C5	65.2 (7)
O3—S1—C9—C14	37.2 (3)	C3—C4—C5—C6	−49.4 (7)
C8—S1—C9—C10	105.2 (3)	C4—C5—C6—C1	34.9 (6)
C8—S1—C9—C14	−76.6 (3)	C4—C5—C6—C7	−75.4 (6)
C8—C1—C2—C3	144.8 (4)	C5—C6—C7—C8	143.5 (4)
O1—C1—C2—C3	−84.0 (4)	C1—C6—C7—C8	18.3 (3)
O1—C1—C2—C21	43.7 (4)	C6—C7—C8—S1	100.7 (3)
C6—C1—C2—C3	47.5 (5)	C6—C7—C8—C1	−17.7 (3)
C6—C1—C2—C21	175.2 (3)	S1—C9—C10—C11	177.6 (3)
C8—C1—C6—C7	−17.9 (3)	C10—C9—C14—C13	1.8 (6)
O1—C1—C8—S1	24.9 (4)	C14—C9—C10—C11	−0.6 (6)
O1—C1—C8—C7	138.4 (3)	S1—C9—C14—C13	−176.5 (3)
C2—C1—C8—S1	149.4 (3)	C9—C10—C11—C12	−1.1 (6)
C2—C1—C8—C7	−97.1 (3)	C10—C11—C12—C13	1.6 (6)
C6—C1—C8—S1	−95.7 (3)	C11—C12—C13—C14	−0.4 (6)
C6—C1—C8—C7	17.8 (3)	C12—C13—C14—C9	−1.3 (6)

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+2, −y+1, −z+2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+2, −y, −z+2; (v) x+1/2, −y+1/2, z−1/2; (vi) −x+3/2, y−1/2, −z+3/2; (vii) −x+3/2, y−1/2, −z+5/2; (viii) x−1/2, −y+1/2, z−1/2; (ix) x−1/2, −y+1/2, z+1/2; (x) −x+3/2, y+1/2, −z+5/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.96	2.44	3.036 (4)	120
O1—H1···O2^ii	0.96	2.02	2.918 (3)	154
C10—H10···O2	0.9600	2.5500	2.935 (5)	104.00
C13—H13···O1^vi	0.9400	2.5800	3.291 (5)	132.00
C14—H14···O3^iv	0.9500	2.5600	3.444 (4)	155.00

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