(1S,2R,2'S)- and (1S,2S,2'S)-1-phenyl-2-phenyl­thio-2-(tetra­hydro­pyran-2'-yl­thio)­ethanol diastereoisomers at 193 K

In the synthesis of 1-phenyl-2-phenyl­thio-2-(tetra­hydro­pyran-2-yl­thio)­ethanol, C₁₉H₂₂O₂S₂, four diastereoisomers are formed. Two non-centrosymmetric enantiomeric forms which crystallize in space groups P2₁2₁2₁ and Pna2₁ are presented. The former has an intramolecular hydrogen bond between the hydroxyl group and the O atom of the tetra­hydro­pyran ring. In the latter isomer, the hydroxyl group forms an intermolecular hydrogen bond to the O atom of the tetra­hydro­pyran­yl group of a neighbouring mol­ecule, joining the mol­ecules into chains in the c-axis direction; the O...O distances are 2.962 (4) and 2.764 (3) Å, respectively. The tetra­hydro­pyran rings are in chair conformations in both isomers and the S side chain has an equatorial orientation in the former, but an axial orientation in the latter mol­ecule.

Computing details

For both compounds, data collection: AFC7S Software (Molecular Structure Corporation, 1996); cell refinement: AFC7S Software; data reduction: TEXSAN (Molecular Structure Corporation, 1993); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C19H22O2S2	Dx = 1.301 Mg m^−3
Mr = 346.49	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 5.3170 (11) Å	θ = 4–10°
b = 16.642 (3) Å	µ = 0.31 mm^−1
c = 19.998 (4) Å	T = 193 K
V = 1769.5 (6) Å^3	Prismatic, colourless
Z = 4	0.31 × 0.22 × 0.16 mm
F(000) = 736

Data collection

Rigaku AFC7S diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 26.5°, θmin = 2.7°
Graphite monochromator	h = 0→6
ω/2θ scans	k = 0→20
2057 measured reflections	l = 0→24
2057 independent reflections	3 standard reflections every 100 reflections
1850 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.105	Calculated w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.7649P] where P = (Fo^2 + 2Fc^2)/3'
S = 1.03	(Δ/σ)max < 0.001
2057 reflections	Δρmax = 0.29 e Å^−3
208 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.22 (13)

Special details

Experimental. The HPLC separation experiments were performed with an ISCO model 2350 liquid chromatograph equipped with a Shimadzu SPD-6 A UV spectrophotometric detector and a Shimadzu C—R6A Chromatopac. Components were monitored measuring the absorption at 254 nm. The column used was Lichrocart Si 60 (250 × 10 mm ID), 5 µm. The mobile phase was 2% ethyl acetate in dichloromethane; flow rate, 7 ml min^-1.

¹H, ¹³C and DEPT spectra were taken for samples in CDCl₃ with a Varian Gemini 200 and the HMQC spectra with Varian INOVA 300 spectrometer with SiMe₄ as an internal reference. The assigments are based on chemical shift data and DEPT and HMQC measurements. The melting points were determined in an open capillary tube with an Electrothermal apparatus and are uncorrected.

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
S1	1.26462 (17)	0.47735 (5)	0.00516 (4)	0.0363 (2)
S2	0.88768 (19)	0.60495 (5)	0.04884 (4)	0.0384 (2)
O1	0.7835 (7)	0.48305 (15)	0.15859 (12)	0.0597 (9)
H1A	0.8064	0.5303	0.1721	0.090*
O2	1.0779 (6)	0.63379 (14)	0.16727 (12)	0.0482 (7)
C1	0.9723 (6)	0.49922 (18)	0.04820 (15)	0.0304 (7)
H1B	0.8363	0.4705	0.0232	0.036*
C2	0.9880 (8)	0.45946 (19)	0.11838 (15)	0.0366 (8)
H2A	1.1479	0.4766	0.1405	0.044*
C3	1.1852 (6)	0.50034 (18)	−0.07910 (14)	0.0308 (7)
C4	1.3445 (8)	0.5496 (2)	−0.11490 (17)	0.0402 (8)
H4A	1.4859	0.5735	−0.0938	0.048*
C5	1.2957 (9)	0.5638 (2)	−0.18224 (19)	0.0496 (10)
H5A	1.4079	0.5962	−0.2076	0.060*
C6	1.0872 (8)	0.5315 (2)	−0.21240 (16)	0.0439 (9)
H6A	1.0522	0.5428	−0.2580	0.053*
C7	0.9292 (8)	0.4827 (2)	−0.17626 (17)	0.0437 (9)
H7A	0.7846	0.4603	−0.1970	0.052*
C8	0.9795 (7)	0.4658 (2)	−0.10961 (16)	0.0392 (8)
H8A	0.8728	0.4307	−0.0852	0.047*
C9	0.9842 (7)	0.36797 (19)	0.11338 (16)	0.0351 (8)
C10	0.7932 (8)	0.3282 (2)	0.0798 (2)	0.0482 (10)
H10A	0.6619	0.3578	0.0591	0.058*
C11	0.7943 (9)	0.2447 (2)	0.0765 (2)	0.0530 (10)
H11A	0.6658	0.2176	0.0524	0.064*
C12	0.9786 (8)	0.2013 (2)	0.1076 (2)	0.0481 (10)
H12A	0.9745	0.1442	0.1063	0.058*
C13	1.1693 (9)	0.2400 (2)	0.1406 (2)	0.0536 (11)
H13A	1.2992	0.2098	0.1615	0.064*
C14	1.1722 (8)	0.3240 (2)	0.14358 (17)	0.0427 (9)
H14A	1.3043	0.3509	0.1665	0.051*
C15	1.1346 (8)	0.6476 (2)	0.09864 (17)	0.0384 (8)
H15A	1.2974	0.6208	0.0873	0.046*
C16	1.1559 (9)	0.7374 (2)	0.08451 (18)	0.0495 (10)
H16A	1.2022	0.7460	0.0371	0.059*
H16B	0.9918	0.7638	0.0927	0.059*
C17	1.3556 (10)	0.7739 (2)	0.1299 (2)	0.0594 (11)
H17A	1.5233	0.7537	0.1166	0.071*
H17B	1.3556	0.8331	0.1245	0.071*
C18	1.3075 (11)	0.7532 (2)	0.2021 (2)	0.0634 (13)
H18A	1.1539	0.7810	0.2178	0.076*
H18B	1.4505	0.7715	0.2299	0.076*
C19	1.2748 (12)	0.6630 (2)	0.2097 (2)	0.0631 (14)
H19A	1.4344	0.6357	0.1982	0.076*
H19B	1.2344	0.6503	0.2568	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0327 (4)	0.0421 (4)	0.0340 (4)	0.0067 (4)	0.0005 (4)	0.0015 (4)
S2	0.0409 (5)	0.0312 (4)	0.0431 (4)	0.0064 (4)	−0.0027 (4)	0.0017 (3)
O1	0.089 (2)	0.0382 (13)	0.0519 (14)	0.0061 (18)	0.0324 (17)	0.0001 (12)
O2	0.072 (2)	0.0333 (12)	0.0394 (12)	−0.0010 (15)	0.0013 (15)	−0.0010 (10)
C1	0.0284 (16)	0.0301 (15)	0.0327 (15)	0.0046 (14)	0.0016 (14)	−0.0008 (13)
C2	0.050 (2)	0.0276 (16)	0.0323 (15)	0.0022 (17)	0.0043 (17)	0.0010 (13)
C3	0.0342 (18)	0.0276 (14)	0.0306 (14)	0.0073 (14)	0.0028 (13)	−0.0019 (12)
C4	0.039 (2)	0.0384 (18)	0.0428 (17)	−0.0074 (17)	0.0002 (17)	−0.0015 (15)
C5	0.059 (3)	0.043 (2)	0.0464 (18)	−0.006 (2)	0.010 (2)	0.0096 (16)
C6	0.054 (2)	0.0451 (19)	0.0325 (15)	0.004 (2)	−0.0005 (18)	0.0005 (15)
C7	0.045 (2)	0.048 (2)	0.0381 (16)	−0.003 (2)	−0.0038 (17)	−0.0099 (16)
C8	0.040 (2)	0.0385 (18)	0.0396 (17)	−0.0101 (17)	0.0044 (17)	−0.0017 (14)
C9	0.043 (2)	0.0299 (16)	0.0326 (15)	−0.0017 (16)	0.0030 (16)	0.0008 (13)
C10	0.039 (2)	0.0381 (19)	0.067 (2)	0.0046 (19)	−0.008 (2)	0.0081 (17)
C11	0.045 (2)	0.043 (2)	0.072 (2)	−0.008 (2)	−0.007 (2)	−0.0025 (18)
C12	0.052 (2)	0.0294 (17)	0.063 (2)	0.0003 (18)	0.002 (2)	−0.0012 (17)
C13	0.062 (3)	0.0367 (19)	0.062 (2)	0.007 (2)	−0.008 (2)	0.0010 (18)
C14	0.052 (3)	0.0338 (17)	0.0424 (17)	−0.0026 (18)	−0.0079 (19)	−0.0009 (14)
C15	0.041 (2)	0.0314 (16)	0.0426 (17)	0.0022 (17)	0.0024 (18)	0.0012 (14)
C16	0.061 (3)	0.0361 (18)	0.051 (2)	−0.006 (2)	−0.004 (2)	0.0064 (16)
C17	0.057 (3)	0.039 (2)	0.082 (3)	−0.001 (2)	−0.014 (3)	−0.002 (2)
C18	0.082 (4)	0.040 (2)	0.069 (3)	−0.001 (2)	−0.021 (3)	−0.0125 (19)
C19	0.097 (4)	0.039 (2)	0.053 (2)	0.010 (3)	−0.022 (3)	−0.0084 (17)

Geometric parameters (Å, º)

S1—C3	1.779 (3)	C6—C7	1.374 (5)
S1—C1	1.814 (3)	C7—C8	1.388 (5)
S2—C15	1.794 (4)	C9—C14	1.378 (5)
S2—C1	1.816 (3)	C9—C10	1.386 (5)
O1—C2	1.408 (5)	C10—C11	1.391 (5)
O2—C15	1.424 (4)	C11—C12	1.367 (6)
O2—C19	1.433 (5)	C12—C13	1.371 (6)
C1—C2	1.554 (4)	C13—C14	1.400 (5)
C2—C9	1.526 (4)	C15—C16	1.525 (5)
C3—C8	1.378 (5)	C16—C17	1.523 (6)
C3—C4	1.379 (5)	C17—C18	1.508 (6)
C4—C5	1.392 (5)	C18—C19	1.518 (5)
C5—C6	1.372 (6)
C3—S1—C1	101.71 (15)	C3—C8—C7	119.6 (3)
C15—S2—C1	101.86 (16)	C14—C9—C10	119.4 (3)
C15—O2—C19	111.2 (3)	C14—C9—C2	119.4 (3)
C2—C1—S1	107.3 (2)	C10—C9—C2	121.2 (3)
C2—C1—S2	114.8 (2)	C9—C10—C11	119.8 (4)
S1—C1—S2	114.20 (17)	C12—C11—C10	120.6 (4)
O1—C2—C9	107.8 (3)	C11—C12—C13	120.1 (4)
O1—C2—C1	110.8 (3)	C12—C13—C14	119.9 (4)
C9—C2—C1	111.4 (3)	C9—C14—C13	120.2 (4)
C8—C3—C4	120.4 (3)	O2—C15—C16	110.6 (3)
C8—C3—S1	121.2 (3)	O2—C15—S2	108.4 (3)
C4—C3—S1	118.3 (3)	C16—C15—S2	109.8 (3)
C3—C4—C5	119.3 (4)	C17—C16—C15	109.4 (3)
C6—C5—C4	120.6 (4)	C18—C17—C16	111.2 (4)
C5—C6—C7	119.6 (3)	C17—C18—C19	110.0 (3)
C6—C7—C8	120.5 (4)	O2—C19—C18	111.1 (4)
C3—S1—C1—C2	164.2 (2)	O1—C2—C9—C10	67.3 (4)
C3—S1—C1—S2	−67.4 (2)	C1—C2—C9—C10	−54.5 (5)
C15—S2—C1—C2	58.9 (3)	C14—C9—C10—C11	−0.5 (6)
C15—S2—C1—S1	−65.6 (2)	C2—C9—C10—C11	−179.6 (4)
S1—C1—C2—O1	171.7 (2)	C9—C10—C11—C12	1.7 (7)
S2—C1—C2—O1	43.6 (4)	C10—C11—C12—C13	−2.1 (6)
S1—C1—C2—C9	−68.3 (3)	C11—C12—C13—C14	1.3 (6)
S2—C1—C2—C9	163.6 (3)	C10—C9—C14—C13	−0.4 (6)
C1—S1—C3—C8	−54.0 (3)	C2—C9—C14—C13	178.8 (3)
C1—S1—C3—C4	130.3 (3)	C12—C13—C14—C9	0.0 (6)
C8—C3—C4—C5	−0.2 (5)	C19—O2—C15—C16	−62.4 (4)
S1—C3—C4—C5	175.5 (3)	C19—O2—C15—S2	177.2 (2)
C3—C4—C5—C6	2.1 (6)	C1—S2—C15—O2	−80.0 (3)
C4—C5—C6—C7	−2.0 (6)	C1—S2—C15—C16	159.1 (3)
C5—C6—C7—C8	−0.1 (6)	O2—C15—C16—C17	57.1 (5)
C4—C3—C8—C7	−1.8 (5)	S2—C15—C16—C17	176.8 (3)
S1—C3—C8—C7	−177.4 (3)	C15—C16—C17—C18	−52.5 (5)
C6—C7—C8—C3	2.0 (6)	C16—C17—C18—C19	52.1 (6)
O1—C2—C9—C14	−111.8 (4)	C15—O2—C19—C18	61.9 (5)
C1—C2—C9—C14	126.4 (4)	C17—C18—C19—O2	−56.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.84	2.25	2.962 (4)	143

(II)

Crystal data

C19H22O2S2	Dx = 1.326 Mg m^−3
Mr = 346.49	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 25 reflections
a = 16.699 (3) Å	θ = 4–10°
b = 18.507 (4) Å	µ = 0.31 mm^−1
c = 5.6150 (11) Å	T = 193 K
V = 1735.3 (6) Å^3	Prismatic, colourless
Z = 4	0.38 × 0.26 × 0.22 mm
F(000) = 736

Data collection

Rigaku AFC7S diffractometer	Rint = 0.070
Radiation source: fine-focus sealed tube	θmax = 26.5°, θmin = 2.5°
Graphite monochromator	h = −20→20
ω/2θ scans	k = −23→23
7318 measured reflections	l = 0→7
1955 independent reflections	3 standard reflections every 100 reflections
1842 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.083	Calculated w = 1/[σ^2(Fo^2) + (0.0535P)^2 + 0.1178P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
1955 reflections	Δρmax = 0.25 e Å^−3
212 parameters	Δρmin = −0.43 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

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
S1	0.23623 (4)	0.70736 (3)	0.17049 (13)	0.03011 (16)
S2	0.38132 (4)	0.64424 (3)	0.39707 (13)	0.02748 (16)
O1	0.37724 (12)	0.79253 (10)	0.0716 (4)	0.0320 (5)
H1B	0.4084 (19)	0.7668 (18)	0.035 (8)	0.046 (10)*
O2	0.46600 (11)	0.71428 (8)	0.7459 (3)	0.0290 (4)
C1	0.31414 (13)	0.72258 (11)	0.3906 (5)	0.0245 (5)
H1C	0.2892	0.7292	0.5511	0.029*
C2	0.35963 (15)	0.79237 (12)	0.3199 (5)	0.0252 (5)
H2A	0.4112	0.7940	0.4101	0.030*
C3	0.16364 (14)	0.65281 (11)	0.3183 (5)	0.0242 (5)
C4	0.17452 (15)	0.61730 (13)	0.5342 (5)	0.0285 (5)
H4B	0.2235	0.6219	0.6189	0.034*
C5	0.11303 (15)	0.57505 (14)	0.6243 (5)	0.0346 (6)
H5A	0.1204	0.5505	0.7713	0.041*
C6	0.04094 (16)	0.56805 (14)	0.5035 (6)	0.0378 (6)
H6A	−0.0009	0.5393	0.5677	0.045*
C7	0.03066 (16)	0.60348 (13)	0.2885 (6)	0.0339 (6)
H7B	−0.0183	0.5986	0.2038	0.041*
C8	0.09133 (15)	0.64597 (12)	0.1964 (5)	0.0300 (6)
H8B	0.0837	0.6706	0.0496	0.036*
C9	0.31300 (14)	0.86086 (11)	0.3734 (5)	0.0240 (5)
C10	0.26004 (14)	0.89072 (13)	0.2068 (5)	0.0286 (5)
H10C	0.2510	0.8670	0.0592	0.034*
C11	0.22089 (16)	0.95500 (14)	0.2578 (6)	0.0338 (6)
H11C	0.1847	0.9749	0.1451	0.041*
C12	0.23407 (16)	0.99016 (14)	0.4702 (6)	0.0357 (7)
H12B	0.2076	1.0345	0.5022	0.043*
C13	0.28526 (16)	0.96144 (13)	0.6358 (5)	0.0356 (6)
H13B	0.2936	0.9856	0.7829	0.043*
C14	0.32537 (16)	0.89631 (13)	0.5884 (5)	0.0296 (6)
H14B	0.3609	0.8765	0.7033	0.036*
C15	0.42028 (15)	0.65086 (12)	0.7034 (5)	0.0262 (5)
H15B	0.3728	0.6530	0.8118	0.031*
C16	0.46675 (16)	0.58295 (13)	0.7683 (6)	0.0346 (6)
H16B	0.4722	0.5802	0.9436	0.041*
H16C	0.4362	0.5400	0.7150	0.041*
C17	0.54955 (15)	0.58140 (13)	0.6559 (7)	0.0382 (6)
H17B	0.5445	0.5755	0.4813	0.046*
H17C	0.5801	0.5397	0.7187	0.046*
C18	0.59453 (16)	0.65137 (15)	0.7110 (7)	0.0403 (7)
H18C	0.6055	0.6548	0.8839	0.048*
H18D	0.6463	0.6522	0.6250	0.048*
C19	0.54267 (15)	0.71439 (13)	0.6321 (5)	0.0324 (6)
H19A	0.5706	0.7602	0.6693	0.039*
H19B	0.5351	0.7120	0.4574	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0326 (3)	0.0331 (3)	0.0247 (3)	−0.0056 (2)	−0.0049 (3)	0.0032 (3)
S2	0.0314 (3)	0.0225 (3)	0.0286 (3)	0.0036 (2)	−0.0006 (3)	−0.0045 (3)
O1	0.0367 (11)	0.0294 (9)	0.0298 (10)	0.0070 (8)	0.0112 (9)	0.0004 (8)
O2	0.0349 (9)	0.0249 (8)	0.0272 (9)	0.0041 (7)	0.0015 (8)	−0.0063 (7)
C1	0.0269 (11)	0.0226 (10)	0.0240 (11)	0.0027 (8)	−0.0024 (11)	−0.0020 (10)
C2	0.0264 (12)	0.0246 (11)	0.0247 (12)	0.0014 (9)	0.0011 (10)	0.0004 (10)
C3	0.0267 (12)	0.0189 (10)	0.0269 (12)	−0.0005 (8)	0.0003 (10)	−0.0032 (10)
C4	0.0330 (13)	0.0271 (12)	0.0253 (12)	0.0054 (10)	−0.0037 (11)	−0.0021 (11)
C5	0.0409 (14)	0.0296 (12)	0.0331 (15)	0.0063 (10)	0.0034 (12)	0.0036 (12)
C6	0.0355 (14)	0.0287 (13)	0.0492 (17)	0.0020 (10)	0.0081 (14)	0.0006 (13)
C7	0.0290 (13)	0.0285 (12)	0.0443 (16)	0.0009 (10)	−0.0066 (12)	−0.0069 (12)
C8	0.0341 (13)	0.0257 (12)	0.0301 (14)	0.0030 (9)	−0.0035 (12)	−0.0030 (11)
C9	0.0266 (11)	0.0207 (10)	0.0245 (12)	−0.0022 (8)	0.0030 (10)	0.0015 (10)
C10	0.0322 (12)	0.0287 (11)	0.0251 (14)	0.0017 (9)	0.0019 (11)	−0.0002 (11)
C11	0.0360 (13)	0.0311 (13)	0.0344 (14)	0.0061 (10)	0.0025 (12)	0.0071 (11)
C12	0.0412 (15)	0.0226 (12)	0.0434 (17)	0.0013 (10)	0.0184 (13)	0.0005 (12)
C13	0.0507 (15)	0.0283 (12)	0.0278 (14)	−0.0076 (11)	0.0107 (13)	−0.0065 (11)
C14	0.0370 (14)	0.0308 (12)	0.0210 (12)	−0.0042 (10)	0.0022 (10)	−0.0010 (10)
C15	0.0261 (12)	0.0259 (11)	0.0267 (12)	0.0022 (8)	0.0024 (10)	0.0013 (10)
C16	0.0362 (14)	0.0286 (12)	0.0389 (15)	−0.0002 (10)	−0.0033 (13)	0.0086 (12)
C17	0.0371 (13)	0.0287 (12)	0.0490 (16)	0.0101 (10)	−0.0005 (15)	−0.0048 (13)
C18	0.0273 (13)	0.0441 (16)	0.0496 (19)	0.0008 (10)	0.0027 (13)	−0.0059 (14)
C19	0.0355 (13)	0.0297 (12)	0.0319 (14)	−0.0087 (9)	0.0049 (12)	−0.0031 (11)

Geometric parameters (Å, º)

S1—C3	1.783 (2)	C6—C7	1.385 (5)
S1—C1	1.816 (3)	C7—C8	1.383 (4)
S2—C1	1.834 (2)	C9—C14	1.389 (4)
S2—C15	1.843 (3)	C9—C10	1.401 (4)
O1—C2	1.425 (3)	C10—C11	1.387 (4)
O2—C15	1.420 (3)	C11—C12	1.376 (4)
O2—C19	1.431 (3)	C12—C13	1.370 (4)
C1—C2	1.550 (3)	C13—C14	1.404 (3)
C2—C9	1.518 (3)	C15—C16	1.521 (3)
C3—C4	1.391 (4)	C16—C17	1.520 (4)
C3—C8	1.394 (4)	C17—C18	1.529 (4)
C4—C5	1.386 (4)	C18—C19	1.519 (4)
C5—C6	1.388 (4)
C3—S1—C1	104.95 (12)	C7—C8—C3	120.2 (3)
C1—S2—C15	100.48 (12)	C14—C9—C10	119.2 (2)
C15—O2—C19	114.04 (18)	C14—C9—C2	119.3 (2)
C2—C1—S1	107.81 (18)	C10—C9—C2	121.4 (2)
C2—C1—S2	111.34 (16)	C11—C10—C9	119.9 (3)
S1—C1—S2	109.22 (12)	C12—C11—C10	120.6 (3)
O1—C2—C9	107.3 (2)	C13—C12—C11	120.3 (2)
O1—C2—C1	110.7 (2)	C12—C13—C14	120.1 (3)
C9—C2—C1	113.2 (2)	C9—C14—C13	119.9 (2)
C4—C3—C8	119.9 (2)	O2—C15—C16	111.6 (2)
C4—C3—S1	125.77 (19)	O2—C15—S2	113.66 (17)
C8—C3—S1	114.3 (2)	C16—C15—S2	110.40 (18)
C3—C4—C5	119.2 (2)	C17—C16—C15	112.4 (2)
C6—C5—C4	121.1 (3)	C16—C17—C18	110.3 (2)
C5—C6—C7	119.3 (3)	C19—C18—C17	108.1 (2)
C8—C7—C6	120.3 (3)	O2—C19—C18	112.3 (2)
C3—S1—C1—C2	−156.81 (15)	O1—C2—C9—C10	33.5 (3)
C3—S1—C1—S2	82.08 (15)	C1—C2—C9—C10	−88.9 (3)
C15—S2—C1—C2	86.5 (2)	C14—C9—C10—C11	0.1 (4)
C15—S2—C1—S1	−154.53 (13)	C2—C9—C10—C11	−177.3 (2)
S1—C1—C2—O1	−45.4 (2)	C9—C10—C11—C12	0.5 (4)
S2—C1—C2—O1	74.4 (3)	C10—C11—C12—C13	−1.0 (4)
S1—C1—C2—C9	75.2 (2)	C11—C12—C13—C14	0.8 (4)
S2—C1—C2—C9	−165.03 (19)	C10—C9—C14—C13	−0.3 (3)
C1—S1—C3—C4	−12.9 (2)	C2—C9—C14—C13	177.2 (2)
C1—S1—C3—C8	168.43 (18)	C12—C13—C14—C9	−0.1 (4)
C8—C3—C4—C5	0.4 (3)	C19—O2—C15—C16	54.1 (3)
S1—C3—C4—C5	−178.25 (19)	C19—O2—C15—S2	−71.6 (2)
C3—C4—C5—C6	−0.4 (4)	C1—S2—C15—O2	−64.06 (18)
C4—C5—C6—C7	0.5 (4)	C1—S2—C15—C16	169.66 (17)
C5—C6—C7—C8	−0.7 (4)	O2—C15—C16—C17	−50.8 (3)
C6—C7—C8—C3	0.7 (4)	S2—C15—C16—C17	76.7 (3)
C4—C3—C8—C7	−0.6 (4)	C15—C16—C17—C18	52.1 (4)
S1—C3—C8—C7	178.24 (19)	C16—C17—C18—C19	−54.3 (4)
O1—C2—C9—C14	−143.9 (2)	C15—O2—C19—C18	−59.2 (3)
C1—C2—C9—C14	93.6 (3)	C17—C18—C19—O2	57.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O2^i	0.74 (3)	2.12 (4)	2.764 (3)	146 (4)

Symmetry code: (i) x, y, z−1.