A second monoclinic polymorph of S-­(4-tolyl) 4-toluenethiosulfonate at 150 and 293 K

The title compound, C₁₄H₁₄O₂S₂, contains discrete mol­ecules and is a polymorph of a structure reported previously by Caputo, Palumbo, Nardelli & Pelizzi [Gazz. Chim. Ital. (1984), 114, 421-430]. The present structure contains no intermolecular C-H...O hydrogen bonds, whereas in the previous polymorph, the mol­ecules are linked into continuous chains by such interactions.

Computing details

For both compounds, data collection: Kappa-CCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

(Ia) S-(4-tolyl) 4-toluenethiosulfonate at 150 K

Crystal data

C14H14O2S2	F(000) = 584
Mr = 278.37	Dx = 1.418 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.1835 (11) Å	Cell parameters from 2266 reflections
b = 6.5050 (4) Å	θ = 1.5–25.0°
c = 15.2171 (9) Å	µ = 0.40 mm^−1
β = 92.217 (4)°	T = 150 K
V = 1304.02 (16) Å^3	Lath, colourless
Z = 4	0.30 × 0.20 × 0.15 mm

Data collection

Nonius Kappa-CCD diffractometer	2266 independent reflections
Radiation source: fine-focus sealed X-ray tube	1849 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ scans and ω scans with κ offsets	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −15→15
Tmin = 0.890, Tmax = 0.943	k = −7→7
7404 measured reflections	l = −17→18

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.056P)^2 + 0.9064P] where P = (Fo^2 + 2Fc^2)/3
2266 reflections	(Δ/σ)max = 0.003
173 parameters	Δρmax = 0.33 e Å^−3
3 restraints	Δρmin = −0.44 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.22172 (4)	0.25543 (9)	0.63560 (4)	0.0220 (2)
S2	0.37885 (5)	0.25166 (9)	0.66447 (4)	0.0248 (2)
O11	0.21343 (14)	0.3765 (3)	0.55591 (10)	0.0268 (4)	0.9375
O12	0.18324 (13)	0.0511 (3)	0.63586 (11)	0.0255 (4)	0.9375
C11	0.16805 (17)	0.3932 (4)	0.72206 (14)	0.0216 (5)
C12	0.13586 (17)	0.5946 (4)	0.70731 (15)	0.0238 (5)
C13	0.09846 (18)	0.7063 (4)	0.77633 (16)	0.0259 (5)
C14	0.09586 (17)	0.6222 (4)	0.86083 (15)	0.0267 (6)
C15	0.12682 (18)	0.4195 (4)	0.87332 (15)	0.0261 (6)
C16	0.16187 (18)	0.3030 (4)	0.80478 (15)	0.0243 (5)
C17	0.0638 (2)	0.7514 (4)	0.93730 (18)	0.0373 (7)
C21	0.38350 (17)	0.0886 (4)	0.75802 (14)	0.0217 (5)
C22	0.36020 (18)	−0.1190 (4)	0.74939 (15)	0.0239 (5)
C23	0.35424 (18)	−0.2400 (4)	0.82388 (16)	0.0249 (6)
C24	0.37296 (17)	−0.1587 (4)	0.90763 (15)	0.0252 (5)
C25	0.39986 (18)	0.0471 (4)	0.91482 (15)	0.0253 (5)
C26	0.40537 (18)	0.1708 (4)	0.84125 (15)	0.0241 (5)
C27	0.3631 (2)	−0.2916 (5)	0.98831 (17)	0.0372 (7)
O21	0.393 (2)	0.4675 (9)	0.6771 (14)	0.030*	0.0625
O22	0.409 (2)	0.144 (3)	0.5880 (10)	0.030*	0.0625
H12	0.1395	0.6546	0.6506	0.029*
H13	0.0742	0.8421	0.7662	0.031*
H15	0.1238	0.3598	0.9301	0.031*
H16	0.1814	0.1638	0.8139	0.029*
H17A	0.0567	0.6637	0.9890	0.056*	0.70 (3)
H17B	−0.0013	0.8176	0.9223	0.056*	0.70 (3)
H17C	0.1153	0.8570	0.9503	0.056*	0.70 (3)
H17D	0.0571	0.8952	0.9187	0.056*	0.30 (3)
H17E	0.1151	0.7413	0.9854	0.056*	0.30 (3)
H17F	−0.0015	0.7019	0.9574	0.056*	0.30 (3)
H22	0.3484	−0.1775	0.6927	0.029*
H23	0.3371	−0.3812	0.8177	0.030*
H25	0.4148	0.1041	0.9713	0.030*
H26	0.4240	0.3113	0.8474	0.029*
H27A	0.3514	−0.2041	1.0394	0.056*	0.61 (3)
H27B	0.4258	−0.3705	0.9988	0.056*	0.61 (3)
H27C	0.3059	−0.3862	0.9791	0.056*	0.61 (3)
H27D	0.3706	−0.4364	0.9721	0.056*	0.39 (3)
H27E	0.2963	−0.2701	1.0127	0.056*	0.39 (3)
H27F	0.4161	−0.2543	1.0324	0.056*	0.39 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0229 (4)	0.0247 (4)	0.0183 (3)	0.0004 (2)	−0.0009 (2)	0.0009 (2)
S2	0.0219 (4)	0.0300 (4)	0.0227 (3)	−0.0006 (2)	0.0028 (2)	0.0036 (2)
O11	0.0321 (10)	0.0312 (11)	0.0170 (8)	0.0013 (8)	−0.0006 (7)	0.0045 (7)
O12	0.0249 (10)	0.0229 (10)	0.0287 (9)	−0.0032 (7)	−0.0013 (7)	−0.0018 (7)
C11	0.0176 (12)	0.0251 (13)	0.0220 (11)	−0.0016 (9)	0.0002 (9)	0.0000 (10)
C12	0.0196 (12)	0.0263 (13)	0.0253 (12)	−0.0034 (10)	−0.0026 (9)	0.0042 (10)
C13	0.0188 (12)	0.0260 (13)	0.0327 (13)	−0.0006 (10)	−0.0012 (10)	−0.0015 (11)
C14	0.0158 (12)	0.0348 (15)	0.0295 (13)	−0.0040 (10)	0.0004 (9)	−0.0051 (11)
C15	0.0195 (12)	0.0380 (15)	0.0210 (11)	−0.0030 (11)	0.0016 (9)	0.0036 (10)
C16	0.0187 (12)	0.0274 (13)	0.0268 (12)	−0.0020 (10)	−0.0007 (9)	0.0043 (10)
C17	0.0298 (16)	0.0476 (19)	0.0348 (15)	0.0013 (12)	0.0040 (12)	−0.0118 (12)
C21	0.0148 (11)	0.0269 (13)	0.0236 (12)	0.0016 (9)	0.0030 (9)	0.0004 (10)
C22	0.0225 (12)	0.0265 (13)	0.0227 (12)	0.0025 (10)	−0.0012 (9)	−0.0036 (10)
C23	0.0203 (13)	0.0228 (13)	0.0314 (13)	0.0003 (9)	−0.0011 (10)	0.0007 (10)
C24	0.0172 (12)	0.0335 (15)	0.0249 (12)	0.0027 (10)	0.0005 (9)	0.0044 (11)
C25	0.0222 (13)	0.0319 (14)	0.0217 (12)	0.0044 (10)	−0.0009 (9)	−0.0033 (10)
C26	0.0209 (12)	0.0241 (13)	0.0269 (12)	0.0024 (10)	−0.0016 (10)	−0.0026 (10)
C27	0.0376 (16)	0.0441 (17)	0.0298 (14)	−0.0006 (13)	0.0005 (12)	0.0107 (12)

Geometric parameters (Å, º)

S1—O11	1.4464 (17)	C17—H17D	0.9800
S1—O12	1.4226 (18)	C17—H17E	0.9800
S1—C11	1.763 (2)	C17—H17F	0.9800
S1—S2	2.1011 (9)	C21—C22	1.390 (3)
S2—O21	1.428 (3)	C21—C26	1.395 (3)
S2—O22	1.429 (3)	C22—C23	1.385 (3)
S2—C21	1.774 (2)	C22—H22	0.9500
C11—C12	1.393 (3)	C23—C24	1.393 (3)
C11—C16	1.394 (3)	C23—H23	0.9500
C12—C13	1.383 (3)	C24—C25	1.388 (4)
C12—H12	0.9500	C24—C27	1.511 (3)
C13—C14	1.399 (3)	C25—C26	1.383 (3)
C13—H13	0.9500	C25—H25	0.9500
C14—C15	1.391 (4)	C26—H26	0.9500
C14—C17	1.509 (3)	C27—H27A	0.9800
C15—C16	1.383 (3)	C27—H27B	0.9800
C15—H15	0.9500	C27—H27C	0.9800
C16—H16	0.9500	C27—H27D	0.9800
C17—H17A	0.9800	C27—H27E	0.9800
C17—H17B	0.9800	C27—H27F	0.9800
C17—H17C	0.9800
O11—S1—O12	119.70 (11)	C14—C17—H17F	109.5
C11—S1—O11	109.23 (11)	H17A—C17—H17F	56.3
C11—S1—O12	108.63 (11)	H17B—C17—H17F	56.3
S1—S2—C21	100.25 (8)	H17C—C17—H17F	141.1
O11—S1—S2	102.92 (8)	H17D—C17—H17F	109.5
O12—S1—S2	109.72 (8)	H17E—C17—H17F	109.5
C11—S1—S2	105.71 (8)	C22—C21—C26	119.7 (2)
O21—S2—O22	123.6 (8)	C22—C21—S2	120.28 (17)
O21—S2—C21	118.6 (9)	C26—C21—S2	119.92 (19)
O22—S2—C21	111.0 (9)	C23—C22—C21	119.6 (2)
O21—S2—S1	97.8 (11)	C23—C22—H22	120.2
O22—S2—S1	98.1 (11)	C21—C22—H22	120.2
C12—C11—C16	120.9 (2)	C22—C23—C24	121.3 (2)
C12—C11—S1	119.12 (17)	C22—C23—H23	119.4
C16—C11—S1	119.93 (19)	C24—C23—H23	119.4
C13—C12—C11	119.1 (2)	C25—C24—C23	118.3 (2)
C13—C12—H12	120.4	C25—C24—C27	121.2 (2)
C11—C12—H12	120.4	C23—C24—C27	120.6 (2)
C12—C13—C14	121.0 (2)	C26—C25—C24	121.2 (2)
C12—C13—H13	119.5	C26—C25—H25	119.4
C14—C13—H13	119.5	C24—C25—H25	119.4
C15—C14—C13	118.6 (2)	C25—C26—C21	119.8 (2)
C15—C14—C17	120.8 (2)	C25—C26—H26	120.1
C13—C14—C17	120.6 (2)	C21—C26—H26	120.1
C16—C15—C14	121.4 (2)	C24—C27—H27A	109.5
C16—C15—H15	119.3	C24—C27—H27B	109.5
C14—C15—H15	119.3	H27A—C27—H27B	109.5
C15—C16—C11	118.9 (2)	C24—C27—H27C	109.5
C15—C16—H16	120.6	H27A—C27—H27C	109.5
C11—C16—H16	120.6	H27B—C27—H27C	109.5
C14—C17—H17A	109.5	C24—C27—H27D	109.5
C14—C17—H17B	109.5	H27A—C27—H27D	141.1
H17A—C17—H17B	109.5	H27B—C27—H27D	56.3
C14—C17—H17C	109.5	H27C—C27—H27D	56.3
H17A—C17—H17C	109.5	C24—C27—H27E	109.5
H17B—C17—H17C	109.5	H27A—C27—H27E	56.3
C14—C17—H17D	109.5	H27B—C27—H27E	141.1
H17A—C17—H17D	141.1	H27C—C27—H27E	56.3
H17B—C17—H17D	56.3	H27D—C27—H27E	109.5
H17C—C17—H17D	56.3	C24—C27—H27F	109.5
C14—C17—H17E	109.5	H27A—C27—H27F	56.3
H17A—C17—H17E	56.3	H27B—C27—H27F	56.3
H17B—C17—H17E	141.1	H27C—C27—H27F	141.1
H17C—C17—H17E	56.3	H27D—C27—H27F	109.5
H17D—C17—H17E	109.5	H27E—C27—H27F	109.5
S1—S2—C21—C22	68.56 (19)	C12—C13—C14—C17	174.4 (2)
S1—S2—C21—C26	−108.05 (18)	C13—C14—C15—C16	1.5 (3)
S2—S1—C11—C12	104.09 (18)	C17—C14—C15—C16	−176.2 (2)
S2—S1—C11—C16	−73.5 (2)	C14—C15—C16—C11	1.4 (4)
O11—S1—S2—C21	−176.52 (11)	C12—C11—C16—C15	−2.5 (3)
O12—S1—S2—C21	−48.04 (11)	S1—C11—C16—C15	175.01 (18)
C11—S1—S2—C21	68.92 (12)	O21—S2—C21—C22	173.4 (12)
O12—S1—S2—O21	−169.1 (9)	O22—S2—C21—C22	−34.3 (12)
O11—S1—S2—O21	62.4 (9)	O21—S2—C21—C26	−3.2 (12)
C11—S1—S2—O21	−52.2 (9)	O22—S2—C21—C26	149.1 (11)
O12—S1—S2—O22	65.1 (9)	C26—C21—C22—C23	3.0 (3)
O11—S1—S2—O22	−63.3 (9)	S2—C21—C22—C23	−173.58 (18)
C11—S1—S2—O22	−177.9 (9)	C21—C22—C23—C24	−1.2 (4)
O12—S1—C11—C12	−138.22 (19)	C22—C23—C24—C25	−1.2 (3)
O11—S1—C11—C12	−6.0 (2)	C22—C23—C24—C27	178.2 (2)
O12—S1—C11—C16	44.2 (2)	C23—C24—C25—C26	1.8 (3)
O11—S1—C11—C16	176.40 (19)	C27—C24—C25—C26	−177.7 (2)
C16—C11—C12—C13	0.8 (3)	C24—C25—C26—C21	0.1 (3)
S1—C11—C12—C13	−176.78 (18)	C22—C21—C26—C25	−2.5 (3)
C11—C12—C13—C14	2.2 (3)	S2—C21—C26—C25	174.12 (18)
C12—C13—C14—C15	−3.3 (3)

(Ib) S-(4-tolyl) 4-toluenethiosulfonate at 293 K

Crystal data

C14H14O2S2	F(000) = 584
Mr = 278.37	Dx = 1.376 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.3579 (7) Å	Cell parameters from 2633 reflections
b = 6.6176 (4) Å	θ = 1.5–26.1°
c = 15.2123 (11) Å	µ = 0.39 mm^−1
β = 92.1322 (19)°	T = 293 K
V = 1343.79 (14) Å^3	Plate, colourless
Z = 4	0.10 × 0.10 × 0.05 mm

Data collection

Nonius Kappa-CCD diffractometer	2633 independent reflections
Radiation source: fine-focus sealed X-ray tube	1451 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
φ scans and ω scans with κ offsets	θmax = 26.1°, θmin = 1.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −15→15
Tmin = 0.962, Tmax = 0.981	k = −7→8
9656 measured reflections	l = −16→18

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0752P)^2] where P = (Fo^2 + 2Fc^2)/3
2633 reflections	(Δ/σ)max = 0.002
173 parameters	Δρmax = 0.32 e Å^−3
3 restraints	Δρmin = −0.32 e Å^−3

Special details

Experimental. Kappa CCD diffractometer using the following programs. Collect: Data collection software, is a graphical user interface written by Enraf–Nonius which encompasses the following programs. DENZO (Otwinowski & Minor, 1997) an indexing and data collection software package and a scaling package, SCALEPACK, both of which programs are produced by the company HKL. Absorption corrections are performed by the SORTAV package (Blessing, 1995 & 1997). High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. Low temperature data are collected using an Oxford Cryosystems cryostream.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.22084 (6)	0.25607 (12)	0.63556 (5)	0.0516 (3)
S2	0.37588 (6)	0.25138 (13)	0.66376 (5)	0.0577 (3)
O11	0.21256 (16)	0.3729 (4)	0.55599 (14)	0.0642 (7)	0.96
O12	0.18280 (16)	0.0557 (3)	0.63676 (15)	0.0621 (6)	0.96
C11	0.1684 (2)	0.3933 (5)	0.72145 (19)	0.0471 (8)
C12	0.1380 (2)	0.5921 (5)	0.7075 (2)	0.0538 (8)
C13	0.1018 (2)	0.7025 (5)	0.7758 (2)	0.0577 (9)
C14	0.0974 (2)	0.6212 (6)	0.8594 (2)	0.0577 (9)
C15	0.1263 (2)	0.4218 (5)	0.8720 (2)	0.0590 (9)
C16	0.1607 (2)	0.3065 (5)	0.8041 (2)	0.0547 (8)
C17	0.0643 (3)	0.7483 (6)	0.9351 (3)	0.0821 (12)
C21	0.3814 (2)	0.0896 (5)	0.75637 (19)	0.0474 (7)
C22	0.3615 (2)	−0.1153 (5)	0.7476 (2)	0.0531 (8)
C23	0.3577 (2)	−0.2366 (5)	0.8208 (2)	0.0568 (9)
C24	0.3742 (2)	−0.1589 (6)	0.9046 (2)	0.0537 (8)
C25	0.3980 (2)	0.0438 (5)	0.9118 (2)	0.0556 (8)
C26	0.4016 (2)	0.1672 (5)	0.8396 (2)	0.0548 (8)
C27	0.3666 (3)	−0.2917 (6)	0.9845 (2)	0.0804 (12)
O21	0.393 (3)	0.4639 (12)	0.672 (2)	0.030*	0.04
O22	0.397 (3)	0.145 (4)	0.5846 (13)	0.030*	0.04
H12	0.1423	0.6502	0.6521	0.065*
H13	0.0798	0.8341	0.7658	0.069*
H15	0.1223	0.3645	0.9276	0.071*
H16	0.1786	0.1722	0.8134	0.066*
H17A	0.0568	0.6641	0.9859	0.123*	0.59 (4)
H17B	0.0013	0.8113	0.9196	0.123*	0.59 (4)
H17C	0.1136	0.8504	0.9483	0.123*	0.59 (4)
H17D	0.0577	0.8865	0.9166	0.123*	0.41 (4)
H17E	0.1131	0.7392	0.9829	0.123*	0.41 (4)
H17F	0.0009	0.7001	0.9542	0.123*	0.41 (4)
H22	0.3507	−0.1709	0.6919	0.064*
H23	0.3437	−0.3735	0.8139	0.068*
H25	0.4120	0.0982	0.9673	0.067*
H26	0.4177	0.3031	0.8466	0.066*
H27A	0.3609	−0.2089	1.0359	0.121*	0.57 (5)
H27B	0.4255	−0.3744	0.9909	0.121*	0.57 (5)
H27C	0.3085	−0.3766	0.9778	0.121*	0.57 (5)
H27D	0.3690	−0.4310	0.9671	0.121*	0.43 (5)
H27E	0.3045	−0.2655	1.0122	0.121*	0.43 (5)
H27F	0.4214	−0.2633	1.0253	0.121*	0.43 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0557 (5)	0.0568 (5)	0.0421 (5)	−0.0021 (4)	−0.0022 (3)	0.0031 (4)
S2	0.0523 (5)	0.0700 (6)	0.0510 (6)	−0.0035 (4)	0.0064 (4)	0.0088 (4)
O11	0.0758 (15)	0.0736 (17)	0.0427 (14)	0.0051 (12)	−0.0027 (11)	0.0117 (12)
O12	0.0631 (14)	0.0552 (15)	0.0674 (16)	−0.0079 (11)	−0.0064 (11)	−0.0033 (12)
C11	0.0440 (16)	0.054 (2)	0.0432 (19)	−0.0040 (14)	0.0000 (13)	0.0054 (15)
C12	0.0556 (19)	0.060 (2)	0.045 (2)	−0.0062 (15)	−0.0027 (14)	0.0099 (17)
C13	0.0523 (19)	0.052 (2)	0.068 (3)	−0.0014 (15)	−0.0013 (16)	−0.0007 (18)
C14	0.0463 (17)	0.073 (3)	0.054 (2)	−0.0072 (16)	0.0015 (14)	−0.0047 (18)
C15	0.0508 (18)	0.078 (3)	0.049 (2)	−0.0037 (17)	0.0041 (14)	0.0098 (19)
C16	0.0487 (17)	0.062 (2)	0.053 (2)	−0.0027 (15)	0.0039 (15)	0.0114 (17)
C17	0.067 (2)	0.107 (3)	0.073 (3)	0.006 (2)	0.0070 (19)	−0.018 (2)
C21	0.0418 (16)	0.056 (2)	0.0447 (19)	0.0015 (14)	0.0016 (13)	−0.0021 (15)
C22	0.0556 (18)	0.059 (2)	0.044 (2)	0.0041 (15)	−0.0034 (14)	−0.0080 (17)
C23	0.062 (2)	0.047 (2)	0.060 (2)	0.0012 (15)	−0.0110 (16)	−0.0028 (18)
C24	0.0456 (17)	0.065 (2)	0.050 (2)	0.0037 (15)	0.0008 (14)	0.0099 (17)
C25	0.0566 (18)	0.065 (2)	0.045 (2)	0.0067 (16)	−0.0026 (14)	−0.0067 (18)
C26	0.0578 (19)	0.0504 (19)	0.056 (2)	0.0010 (15)	−0.0025 (16)	−0.0027 (18)
C27	0.088 (3)	0.095 (3)	0.058 (3)	−0.001 (2)	−0.0039 (19)	0.020 (2)

Geometric parameters (Å, º)

S1—O12	1.420 (2)	C17—H17D	0.9600
S1—O11	1.437 (2)	C17—H17E	0.9600
S1—C11	1.758 (3)	C17—H17F	0.9600
S1—S2	2.0995 (11)	C21—C26	1.384 (4)
S2—O21	1.431 (3)	C21—C22	1.387 (4)
S2—O22	1.431 (3)	C22—C23	1.376 (4)
S2—C21	1.769 (3)	C22—H22	0.9300
C11—C16	1.389 (4)	C23—C24	1.384 (4)
C11—C12	1.391 (4)	C23—H23	0.9300
C12—C13	1.374 (4)	C24—C25	1.382 (4)
C12—H12	0.9300	C24—C27	1.508 (4)
C13—C14	1.384 (4)	C25—C26	1.371 (4)
C13—H13	0.9300	C25—H25	0.9300
C14—C15	1.386 (5)	C26—H26	0.9300
C14—C17	1.506 (5)	C27—H27A	0.9600
C15—C16	1.377 (4)	C27—H27B	0.9600
C15—H15	0.9300	C27—H27C	0.9600
C16—H16	0.9300	C27—H27D	0.9600
C17—H17A	0.9600	C27—H27E	0.9600
C17—H17B	0.9600	C27—H27F	0.9600
C17—H17C	0.9600
O12—S1—O11	119.79 (14)	C14—C17—H17F	109.5
O12—S1—C11	108.65 (14)	H17A—C17—H17F	56.3
O11—S1—C11	109.14 (15)	H17B—C17—H17F	56.3
O12—S1—S2	109.53 (10)	H17C—C17—H17F	141.1
O11—S1—S2	102.97 (10)	H17D—C17—H17F	109.5
C11—S1—S2	105.85 (10)	H17E—C17—H17F	109.5
O21—S2—O22	121.5 (8)	C26—C21—C22	118.8 (3)
O21—S2—C21	121.5 (14)	C26—C21—S2	120.3 (3)
O22—S2—C21	111.6 (13)	C22—C21—S2	120.8 (2)
O21—S2—S1	99.3 (16)	C23—C22—C21	120.3 (3)
O22—S2—S1	93.2 (15)	C23—C22—H22	119.8
C21—S2—S1	100.55 (10)	C21—C22—H22	119.8
C16—C11—C12	119.9 (3)	C22—C23—C24	121.3 (3)
C16—C11—S1	120.3 (2)	C22—C23—H23	119.4
C12—C11—S1	119.8 (2)	C24—C23—H23	119.4
C13—C12—C11	119.8 (3)	C25—C24—C23	117.6 (3)
C13—C12—H12	120.1	C25—C24—C27	121.6 (3)
C11—C12—H12	120.1	C23—C24—C27	120.8 (3)
C12—C13—C14	121.1 (3)	C26—C25—C24	121.9 (3)
C12—C13—H13	119.5	C26—C25—H25	119.0
C14—C13—H13	119.5	C24—C25—H25	119.0
C13—C14—C15	118.4 (3)	C25—C26—C21	120.1 (3)
C13—C14—C17	120.6 (3)	C25—C26—H26	120.0
C15—C14—C17	120.9 (3)	C21—C26—H26	120.0
C16—C15—C14	121.5 (3)	C24—C27—H27A	109.5
C16—C15—H15	119.2	C24—C27—H27B	109.5
C14—C15—H15	119.2	H27A—C27—H27B	109.5
C15—C16—C11	119.2 (3)	C24—C27—H27C	109.5
C15—C16—H16	120.4	H27A—C27—H27C	109.5
C11—C16—H16	120.4	H27B—C27—H27C	109.5
C14—C17—H17A	109.5	C24—C27—H27D	109.5
C14—C17—H17B	109.5	H27A—C27—H27D	141.1
H17A—C17—H17B	109.5	H27B—C27—H27D	56.3
C14—C17—H17C	109.5	H27C—C27—H27D	56.3
H17A—C17—H17C	109.5	C24—C27—H27E	109.5
H17B—C17—H17C	109.5	H27A—C27—H27E	56.3
C14—C17—H17D	109.5	H27B—C27—H27E	141.1
H17A—C17—H17D	141.1	H27C—C27—H27E	56.3
H17B—C17—H17D	56.3	H27D—C27—H27E	109.5
H17C—C17—H17D	56.3	C24—C27—H27F	109.5
C14—C17—H17E	109.5	H27A—C27—H27F	56.3
H17A—C17—H17E	56.3	H27B—C27—H27F	56.3
H17B—C17—H17E	141.1	H27C—C27—H27F	141.1
H17C—C17—H17E	56.3	H27D—C27—H27F	109.5
H17D—C17—H17E	109.5	H27E—C27—H27F	109.5
O12—S1—S2—O21	−171.7 (13)	C17—C14—C15—C16	−177.2 (3)
O11—S1—S2—O21	59.8 (13)	C14—C15—C16—C11	1.2 (4)
C11—S1—S2—O21	−54.7 (13)	C12—C11—C16—C15	−2.3 (4)
O12—S1—S2—O22	65.7 (13)	S1—C11—C16—C15	175.2 (2)
O11—S1—S2—O22	−62.8 (13)	O21—S2—C21—C26	0.9 (18)
C11—S1—S2—O22	−177.3 (13)	O22—S2—C21—C26	155.3 (16)
O12—S1—S2—C21	−46.97 (15)	S1—S2—C21—C26	−106.9 (2)
O11—S1—S2—C21	−175.48 (15)	O21—S2—C21—C22	178.2 (18)
C11—S1—S2—C21	69.99 (15)	O22—S2—C21—C22	−27.4 (16)
O12—S1—C11—C16	43.1 (3)	S1—S2—C21—C22	70.4 (2)
O11—S1—C11—C16	175.4 (2)	C26—C21—C22—C23	2.9 (4)
S2—S1—C11—C16	−74.4 (2)	S2—C21—C22—C23	−174.5 (2)
O12—S1—C11—C12	−139.4 (2)	C21—C22—C23—C24	−0.6 (4)
O11—S1—C11—C12	−7.1 (3)	C22—C23—C24—C25	−2.1 (4)
S2—S1—C11—C12	103.1 (2)	C22—C23—C24—C27	178.0 (3)
C16—C11—C12—C13	0.8 (4)	C23—C24—C25—C26	2.4 (4)
S1—C11—C12—C13	−176.7 (2)	C27—C24—C25—C26	−177.7 (3)
C11—C12—C13—C14	1.8 (4)	C24—C25—C26—C21	−0.2 (4)
C12—C13—C14—C15	−2.9 (4)	C22—C21—C26—C25	−2.5 (4)
C12—C13—C14—C17	175.7 (3)	S2—C21—C26—C25	174.9 (2)
C13—C14—C15—C16	1.3 (4)