1,1,1-Tris(phenyl­sulfonyl­oxymeth­yl)ethane

Fujihara, T.; Shioji, E.; Nagasawa, A.

doi:10.1107/S1600536807035507

1,1,1-Tris(phenylsulfonyloxymethyl)ethane

T. Fujihara, E. Shioji and A. Nagasawa

In the crystal structure of the title compound, C₂₃H₂₄O₉S₃, intermolecular C—H

O hydrogen bonds are found, which link the molecules into a three-dimensional network. Weak C—H

π interactions are also present in the structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035507/at2347sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035507/at2347Isup2.hkl Contains datablock I

CCDC reference: 657861

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Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
R factor = 0.052
wR factor = 0.126
Data-to-parameter ratio = 18.2

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No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.88 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

We report here the title compound, (I) which is the precursor compound for branched acyclic polyamine ligands of the metal cage complexes (Geue & Searle, 1983). The structure of (I), with the atom-numbering scheme, is shown in Fig. 1. The C—C distances in phenyl ring [1.372 (4) - 1.392 (3) Å] are within normal ranges for aromatic systems. The phenyl rings (C6—C11, C12—C17 and C18—C23) are planar, with a largest deviation of 0.0108 (19) Å from the plane being that of atom C12. The S-Csp² bond lengths, viz. S1—C6 [1.754 (2) Å], S2—C12 [1.757 (2) Å] and S3—C18 [1.756 (2) Å], agree with the general S—Csp² bond length (1.75 Å, Allen et al., 1987). Other S—C, S—O, S═O bond lengths are comparable to those found in related structures in that they all contain the p-toluenesulfonyl groups (Kakeya et al., 2006, Manivannan et al., 2005). Analysis of the crystal packing of the title compound shows the existence of the hydrogen-bonding interactions (C—H···O and C—H···π, where Cg1 is the centroid of the ring formed by C12—C17), which connect the neighbouring molecules to form a three-dimensional network as shown in Fig. 2 and Table 1.

Related literature top

Intermolecular C—H···π interactions are also found in the crystal structure of the analogous sulfonate compound (Kakeya et al., 2006). The bond lengths and angles are comparable with those found in related aromatic sulfonates (Kakeya et al., 2006; Manivannan et al., 2005).

For related literature, see: Allen et al. (1987); Fleischer et al. (1971); Geue & Searle (1983).

Experimental top

The title compound (I) was synthesized according to the previously reported method of Fleischer et al. (1971). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution in acetone at 298 K. ¹H NMR (CDCl₃, δ, p.p.m.): 7.54–7.7.84 (m, 15H, C₆H₅), 3.82 (s, 6H, CH₂), 0.92 (s, 3H, CH₃). Analysis calculated for C₂₃H₂₄O₉S₃: C 28.32, H 4.75%. Found: C 51.07, H 4.32%.

Structure description top

For related literature, see: Allen et al. (1987); Fleischer et al. (1971); Geue & Searle (1983).

Computing details top

Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.

Figures top

	Fig. 1. A perspective view of the title compound with the atom-numbering scheme. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. A molecular packing diagram of (I).

1,1,1-Tris(phenylsulfonyloxymethyl)ethane top

Crystal data top

C₂₃H₂₄O₉S₃	Z = 2
M_r = 540.60	F(000) = 564
Triclinic, P1	D_x = 1.469 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8962 (5) Å	Cell parameters from 2403 reflections
b = 14.6650 (14) Å	θ = 2.4–27.7°
c = 15.1812 (14) Å	µ = 0.36 mm⁻¹
α = 69.164 (2)°	T = 173 K
β = 85.096 (3)°	Plate, colourless
γ = 87.685 (2)°	0.21 × 0.12 × 0.11 mm
V = 1222.28 (19) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5782 independent reflections
Radiation source: fine-focus sealed tube	4717 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 8.366 pixels mm^-1	θ_max = 27.9°, θ_min = 1.4°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −19→13
T_min = 0.919, T_max = 0.962	l = −19→19
9027 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.056P)² + 0.5823P] where P = (F_o² + 2F_c²)/3
5782 reflections	(Δ/σ)_max < 0.001
317 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₃H₂₄O₉S₃	γ = 87.685 (2)°
M_r = 540.60	V = 1222.28 (19) Å³
Triclinic, P1	Z = 2
a = 5.8962 (5) Å	Mo Kα radiation
b = 14.6650 (14) Å	µ = 0.36 mm⁻¹
c = 15.1812 (14) Å	T = 173 K
α = 69.164 (2)°	0.21 × 0.12 × 0.11 mm
β = 85.096 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5782 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4717 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.962	R_int = 0.026
9027 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	Δρ_max = 0.52 e Å⁻³
5782 reflections	Δρ_min = −0.34 e Å⁻³
317 parameters

Special details top

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 2.4060 (0.0064) x + 3.1536 (0.0154) y + 13.2033 (0.0089) z = 14.2134 (0.0208)

* 0.0092 (0.0018) C18 * -0.0072 (0.0020) C19 * -0.0003 (0.0022) C20 * 0.0059 (0.0020) C21 * -0.0040 (0.0019) C22 * -0.0036 (0.0018) C23

Rms deviation of fitted atoms = 0.0058

2.1818 (0.0070) x + 13.2877 (0.0075) y + 8.9329 (0.0152) z = 14.2436 (0.0115)

Angle to previous plane (with approximate e.s.d.) = 73.42 (0.09)

* -0.0108 (0.0019) C12 * 0.0080 (0.0019) C13 * 0.0012 (0.0022) C14 * -0.0077 (0.0023) C15 * 0.0050 (0.0024) C16 * 0.0043 (0.0022) C17

Rms deviation of fitted atoms = 0.0069

2.2980 (0.0056) x - 1.4353 (0.0147) y + 12.8260 (0.0084) z = 4.7002 (0.0133)

Angle to previous plane (with approximate e.s.d.) = 73.71 (0.09)

* -0.0005 (0.0016) C6 * -0.0065 (0.0017) C7 * 0.0069 (0.0017) C8 * -0.0001 (0.0018) C9 * -0.0069 (0.0017) C10 * 0.0071 (0.0016) C11

Rms deviation of fitted atoms = 0.0056

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6339 (4)	0.79403 (17)	0.70459 (17)	0.0265 (5)
H1A	0.6937	0.7421	0.6823	0.040*
H1B	0.6493	0.7743	0.7726	0.040*
H1C	0.7197	0.8539	0.6711	0.040*
C2	0.3810 (4)	0.81257 (15)	0.68526 (15)	0.0191 (4)
C3	0.3718 (4)	0.85520 (16)	0.57846 (15)	0.0212 (4)
H3A	0.4453	0.9199	0.5529	0.025*
H3B	0.4542	0.8118	0.5491	0.025*
C4	0.2474 (4)	0.71808 (15)	0.72799 (16)	0.0215 (4)
H4A	0.2671	0.6880	0.7965	0.026*
H4B	0.0833	0.7311	0.7193	0.026*
C5	0.2762 (4)	0.88670 (16)	0.72637 (15)	0.0231 (5)
H5A	0.3603	0.9488	0.6995	0.028*
H5B	0.1154	0.8998	0.7113	0.028*
C6	0.1352 (4)	0.78195 (16)	0.42971 (15)	0.0216 (4)
C7	0.3463 (4)	0.76503 (17)	0.38950 (17)	0.0275 (5)
H7	0.4632	0.8122	0.3728	0.033*
C8	0.3819 (5)	0.67742 (18)	0.37438 (18)	0.0332 (6)
H8	0.5257	0.6638	0.3482	0.040*
C9	0.2103 (5)	0.61014 (18)	0.39704 (18)	0.0345 (6)
H9	0.2365	0.5508	0.3857	0.041*
C10	0.0002 (5)	0.62803 (17)	0.43616 (18)	0.0318 (6)
H10	−0.1177	0.5815	0.4509	0.038*
C11	−0.0376 (4)	0.71391 (16)	0.45363 (16)	0.0265 (5)
H11	−0.1802	0.7262	0.4817	0.032*
C12	0.2772 (4)	0.47976 (16)	0.81194 (17)	0.0278 (5)
C13	0.4939 (4)	0.43840 (18)	0.82266 (19)	0.0350 (6)
H13	0.6065	0.4559	0.7710	0.042*
C14	0.5435 (5)	0.3711 (2)	0.9099 (2)	0.0449 (7)
H14	0.6903	0.3416	0.9182	0.054*
C15	0.3801 (6)	0.3473 (2)	0.9842 (2)	0.0522 (8)
H15	0.4141	0.3007	1.0436	0.063*
C16	0.1677 (6)	0.3903 (2)	0.9735 (2)	0.0553 (9)
H16	0.0570	0.3740	1.0258	0.066*
C17	0.1142 (5)	0.4573 (2)	0.8869 (2)	0.0433 (7)
H17	−0.0324	0.4871	0.8794	0.052*
C18	0.1555 (4)	1.00176 (17)	0.86626 (16)	0.0243 (5)
C19	0.3510 (5)	1.0291 (2)	0.8941 (2)	0.0393 (6)
H19	0.4608	0.9816	0.9243	0.047*
C20	0.3843 (5)	1.1268 (2)	0.8774 (2)	0.0459 (7)
H20	0.5169	1.1467	0.8968	0.055*
C21	0.2256 (5)	1.19530 (19)	0.83256 (19)	0.0387 (6)
H21	0.2489	1.2623	0.8217	0.046*
C22	0.0341 (5)	1.16772 (19)	0.80351 (19)	0.0383 (6)
H22	−0.0734	1.2157	0.7719	0.046*
C23	−0.0027 (4)	1.07034 (18)	0.82008 (18)	0.0317 (5)
H23	−0.1349	1.0509	0.8000	0.038*
O1	0.1335 (2)	0.86482 (11)	0.55679 (10)	0.0215 (3)
O2	0.2426 (3)	0.96243 (11)	0.39114 (11)	0.0297 (4)
O3	−0.1545 (3)	0.91299 (12)	0.44856 (12)	0.0284 (4)
O4	0.3364 (3)	0.65333 (11)	0.67915 (11)	0.0245 (3)
O5	0.3164 (3)	0.51765 (13)	0.63121 (13)	0.0398 (5)
O6	−0.0313 (3)	0.57333 (13)	0.70084 (14)	0.0396 (5)
O7	0.2905 (3)	0.84512 (11)	0.82898 (11)	0.0275 (4)
O8	0.1688 (3)	0.82379 (13)	0.98686 (12)	0.0374 (4)
O9	−0.1156 (3)	0.86594 (13)	0.86820 (13)	0.0374 (4)
S1	0.08321 (9)	0.89170 (4)	0.45003 (4)	0.02113 (14)
S2	0.20808 (10)	0.55550 (4)	0.69854 (4)	0.02768 (15)
S3	0.10533 (10)	0.87705 (4)	0.89391 (4)	0.02641 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0219 (11)	0.0250 (12)	0.0312 (13)	−0.0008 (9)	−0.0027 (9)	−0.0081 (10)
C2	0.0213 (10)	0.0164 (10)	0.0199 (10)	−0.0007 (8)	−0.0028 (8)	−0.0064 (8)
C3	0.0190 (10)	0.0209 (11)	0.0221 (11)	−0.0017 (8)	−0.0015 (8)	−0.0056 (9)
C4	0.0229 (11)	0.0149 (10)	0.0260 (11)	0.0009 (8)	0.0014 (9)	−0.0073 (8)
C5	0.0328 (12)	0.0173 (10)	0.0197 (11)	0.0019 (9)	−0.0041 (9)	−0.0068 (8)
C6	0.0260 (11)	0.0188 (10)	0.0208 (11)	0.0036 (8)	−0.0040 (9)	−0.0080 (8)
C7	0.0290 (12)	0.0272 (12)	0.0279 (12)	0.0002 (10)	0.0001 (10)	−0.0124 (10)
C8	0.0375 (14)	0.0298 (13)	0.0332 (14)	0.0090 (11)	−0.0020 (11)	−0.0136 (11)
C9	0.0551 (17)	0.0216 (12)	0.0292 (13)	0.0068 (11)	−0.0076 (12)	−0.0116 (10)
C10	0.0409 (14)	0.0218 (12)	0.0316 (13)	−0.0051 (10)	−0.0056 (11)	−0.0072 (10)
C11	0.0282 (12)	0.0236 (12)	0.0255 (12)	0.0001 (9)	−0.0032 (9)	−0.0058 (9)
C12	0.0329 (13)	0.0172 (11)	0.0323 (13)	−0.0037 (9)	−0.0063 (10)	−0.0063 (9)
C13	0.0337 (14)	0.0279 (13)	0.0374 (14)	−0.0028 (10)	−0.0053 (11)	−0.0036 (11)
C14	0.0437 (16)	0.0350 (15)	0.0467 (17)	0.0000 (12)	−0.0177 (13)	0.0001 (13)
C15	0.067 (2)	0.0383 (17)	0.0391 (17)	−0.0107 (15)	−0.0143 (15)	0.0047 (13)
C16	0.062 (2)	0.053 (2)	0.0383 (17)	−0.0103 (16)	0.0093 (15)	−0.0034 (14)
C17	0.0398 (16)	0.0391 (16)	0.0446 (17)	−0.0010 (12)	0.0047 (13)	−0.0086 (13)
C18	0.0292 (12)	0.0256 (11)	0.0201 (11)	0.0010 (9)	−0.0012 (9)	−0.0109 (9)
C19	0.0356 (14)	0.0334 (14)	0.0510 (17)	0.0028 (11)	−0.0141 (12)	−0.0154 (13)
C20	0.0412 (16)	0.0418 (16)	0.061 (2)	−0.0094 (13)	−0.0080 (14)	−0.0246 (15)
C21	0.0562 (18)	0.0252 (13)	0.0355 (15)	−0.0045 (12)	0.0013 (13)	−0.0122 (11)
C22	0.0503 (17)	0.0278 (13)	0.0344 (14)	0.0083 (12)	−0.0075 (12)	−0.0080 (11)
C23	0.0327 (13)	0.0328 (13)	0.0329 (13)	0.0046 (11)	−0.0086 (10)	−0.0147 (11)
O1	0.0203 (8)	0.0230 (8)	0.0207 (8)	0.0009 (6)	−0.0007 (6)	−0.0072 (6)
O2	0.0393 (10)	0.0206 (8)	0.0259 (9)	−0.0031 (7)	0.0009 (7)	−0.0046 (7)
O3	0.0272 (9)	0.0280 (9)	0.0300 (9)	0.0079 (7)	−0.0074 (7)	−0.0101 (7)
O4	0.0288 (8)	0.0147 (7)	0.0303 (9)	−0.0003 (6)	0.0009 (7)	−0.0092 (6)
O5	0.0616 (12)	0.0262 (9)	0.0383 (11)	0.0076 (9)	−0.0140 (9)	−0.0181 (8)
O6	0.0321 (10)	0.0276 (9)	0.0570 (13)	−0.0027 (8)	−0.0163 (9)	−0.0093 (9)
O7	0.0380 (9)	0.0248 (8)	0.0217 (8)	0.0081 (7)	−0.0061 (7)	−0.0105 (7)
O8	0.0578 (12)	0.0288 (9)	0.0216 (9)	0.0023 (8)	−0.0039 (8)	−0.0040 (7)
O9	0.0359 (10)	0.0357 (10)	0.0401 (11)	−0.0089 (8)	−0.0011 (8)	−0.0125 (8)
S1	0.0250 (3)	0.0169 (3)	0.0208 (3)	0.0024 (2)	−0.0028 (2)	−0.0058 (2)
S2	0.0335 (3)	0.0164 (3)	0.0345 (3)	−0.0003 (2)	−0.0101 (3)	−0.0091 (2)
S3	0.0344 (3)	0.0226 (3)	0.0220 (3)	−0.0006 (2)	−0.0021 (2)	−0.0075 (2)

Geometric parameters (Å, º) top

C1—C2	1.539 (3)	C13—C14	1.388 (4)
C1—H1A	0.9800	C13—H13	0.9500
C1—H1B	0.9800	C14—C15	1.372 (4)
C1—H1C	0.9800	C14—H14	0.9500
C2—C3	1.521 (3)	C15—C16	1.375 (5)
C2—C5	1.522 (3)	C15—H15	0.9500
C2—C4	1.524 (3)	C16—C17	1.385 (4)
C3—O1	1.461 (2)	C16—H16	0.9500
C3—H3A	0.9900	C17—H17	0.9500
C3—H3B	0.9900	C18—C23	1.381 (3)
C4—O4	1.456 (3)	C18—C19	1.382 (3)
C4—H4A	0.9900	C18—S3	1.756 (2)
C4—H4B	0.9900	C19—C20	1.382 (4)
C5—O7	1.466 (3)	C19—H19	0.9500
C5—H5A	0.9900	C20—C21	1.376 (4)
C5—H5B	0.9900	C20—H20	0.9500
C6—C11	1.388 (3)	C21—C22	1.372 (4)
C6—C7	1.392 (3)	C21—H21	0.9500
C6—S1	1.754 (2)	C22—C23	1.382 (4)
C7—C8	1.388 (3)	C22—H22	0.9500
C7—H7	0.9500	C23—H23	0.9500
C8—C9	1.376 (4)	O1—S1	1.5775 (16)
C8—H8	0.9500	O2—S1	1.4263 (16)
C9—C10	1.384 (4)	O3—S1	1.4239 (16)
C9—H9	0.9500	O4—S2	1.5706 (16)
C10—C11	1.382 (3)	O5—S2	1.4228 (19)
C10—H10	0.9500	O6—S2	1.4247 (19)
C11—H11	0.9500	O7—S3	1.5765 (17)
C12—C17	1.379 (4)	O8—S3	1.4228 (18)
C12—C13	1.389 (3)	O9—S3	1.4231 (19)
C12—S2	1.757 (2)

C2—C1—H1A	109.5	C12—C13—H13	120.5
C2—C1—H1B	109.5	C15—C14—C13	119.9 (3)
H1A—C1—H1B	109.5	C15—C14—H14	120.0
C2—C1—H1C	109.5	C13—C14—H14	120.0
H1A—C1—H1C	109.5	C14—C15—C16	120.7 (3)
H1B—C1—H1C	109.5	C14—C15—H15	119.7
C3—C2—C5	108.18 (17)	C16—C15—H15	119.7
C3—C2—C4	111.32 (17)	C15—C16—C17	120.4 (3)
C5—C2—C4	108.81 (17)	C15—C16—H16	119.8
C3—C2—C1	106.74 (17)	C17—C16—H16	119.8
C5—C2—C1	111.14 (18)	C12—C17—C16	118.9 (3)
C4—C2—C1	110.63 (18)	C12—C17—H17	120.6
O1—C3—C2	108.46 (16)	C16—C17—H17	120.6
O1—C3—H3A	110.0	C23—C18—C19	121.2 (2)
C2—C3—H3A	110.0	C23—C18—S3	119.94 (19)
O1—C3—H3B	110.0	C19—C18—S3	118.86 (19)
C2—C3—H3B	110.0	C20—C19—C18	119.0 (3)
H3A—C3—H3B	108.4	C20—C19—H19	120.5
O4—C4—C2	106.97 (16)	C18—C19—H19	120.5
O4—C4—H4A	110.3	C21—C20—C19	120.1 (3)
C2—C4—H4A	110.3	C21—C20—H20	120.0
O4—C4—H4B	110.3	C19—C20—H20	120.0
C2—C4—H4B	110.3	C22—C21—C20	120.6 (3)
H4A—C4—H4B	108.6	C22—C21—H21	119.7
O7—C5—C2	107.36 (17)	C20—C21—H21	119.7
O7—C5—H5A	110.2	C21—C22—C23	120.2 (3)
C2—C5—H5A	110.2	C21—C22—H22	119.9
O7—C5—H5B	110.2	C23—C22—H22	119.9
C2—C5—H5B	110.2	C18—C23—C22	119.0 (2)
H5A—C5—H5B	108.5	C18—C23—H23	120.5
C11—C6—C7	121.4 (2)	C22—C23—H23	120.5
C11—C6—S1	118.83 (17)	C3—O1—S1	117.30 (13)
C7—C6—S1	119.79 (17)	C4—O4—S2	118.34 (13)
C8—C7—C6	118.3 (2)	C5—O7—S3	118.26 (14)
C8—C7—H7	120.8	O3—S1—O2	120.24 (10)
C6—C7—H7	120.8	O3—S1—O1	104.44 (9)
C9—C8—C7	120.5 (2)	O2—S1—O1	109.50 (9)
C9—C8—H8	119.7	O3—S1—C6	109.04 (10)
C7—C8—H8	119.7	O2—S1—C6	108.75 (10)
C8—C9—C10	120.7 (2)	O1—S1—C6	103.57 (9)
C8—C9—H9	119.6	O5—S2—O6	120.25 (12)
C10—C9—H9	119.6	O5—S2—O4	103.92 (10)
C11—C10—C9	119.8 (2)	O6—S2—O4	109.54 (10)
C11—C10—H10	120.1	O5—S2—C12	108.62 (11)
C9—C10—H10	120.1	O6—S2—C12	108.60 (12)
C10—C11—C6	119.3 (2)	O4—S2—C12	104.83 (10)
C10—C11—H11	120.4	O8—S3—O9	120.10 (11)
C6—C11—H11	120.4	O8—S3—O7	103.38 (10)
C17—C12—C13	121.1 (2)	O9—S3—O7	109.48 (10)
C17—C12—S2	120.2 (2)	O8—S3—C18	109.52 (11)
C13—C12—S2	118.53 (19)	O9—S3—C18	108.91 (11)
C14—C13—C12	119.0 (3)	O7—S3—C18	104.22 (10)
C14—C13—H13	120.5

C5—C2—C3—O1	−65.9 (2)	C21—C22—C23—C18	0.1 (4)
C4—C2—C3—O1	53.6 (2)	C2—C3—O1—S1	−170.43 (13)
C1—C2—C3—O1	174.42 (16)	C2—C4—O4—S2	−171.61 (14)
C3—C2—C4—O4	54.6 (2)	C2—C5—O7—S3	−151.65 (15)
C5—C2—C4—O4	173.71 (17)	C3—O1—S1—O3	−169.93 (14)
C1—C2—C4—O4	−63.9 (2)	C3—O1—S1—O2	−39.92 (17)
C3—C2—C5—O7	−178.97 (17)	C3—O1—S1—C6	75.94 (16)
C4—C2—C5—O7	60.0 (2)	C11—C6—S1—O3	−26.1 (2)
C1—C2—C5—O7	−62.1 (2)	C7—C6—S1—O3	153.34 (18)
C11—C6—C7—C8	−0.5 (4)	C11—C6—S1—O2	−158.96 (18)
S1—C6—C7—C8	179.99 (18)	C7—C6—S1—O2	20.5 (2)
C6—C7—C8—C9	1.2 (4)	C11—C6—S1—O1	84.64 (19)
C7—C8—C9—C10	−0.7 (4)	C7—C6—S1—O1	−95.88 (19)
C8—C9—C10—C11	−0.7 (4)	C4—O4—S2—O5	171.92 (16)
C9—C10—C11—C6	1.3 (4)	C4—O4—S2—O6	42.22 (18)
C7—C6—C11—C10	−0.7 (3)	C4—O4—S2—C12	−74.13 (17)
S1—C6—C11—C10	178.72 (18)	C17—C12—S2—O5	−139.7 (2)
C17—C12—C13—C14	2.0 (4)	C13—C12—S2—O5	36.1 (2)
S2—C12—C13—C14	−173.8 (2)	C17—C12—S2—O6	−7.3 (3)
C12—C13—C14—C15	−0.8 (4)	C13—C12—S2—O6	168.50 (19)
C13—C14—C15—C16	−0.7 (5)	C17—C12—S2—O4	109.7 (2)
C14—C15—C16—C17	1.1 (5)	C13—C12—S2—O4	−74.5 (2)
C13—C12—C17—C16	−1.6 (4)	C5—O7—S3—O8	179.79 (15)
S2—C12—C17—C16	174.1 (2)	C5—O7—S3—O9	50.67 (18)
C15—C16—C17—C12	0.1 (5)	C5—O7—S3—C18	−65.71 (17)
C23—C18—C19—C20	1.7 (4)	C23—C18—S3—O8	−137.7 (2)
S3—C18—C19—C20	−176.2 (2)	C19—C18—S3—O8	40.3 (2)
C18—C19—C20—C21	−0.8 (5)	C23—C18—S3—O9	−4.5 (2)
C19—C20—C21—C22	−0.4 (5)	C19—C18—S3—O9	173.4 (2)
C20—C21—C22—C23	0.8 (4)	C23—C18—S3—O7	112.2 (2)
C19—C18—C23—C22	−1.4 (4)	C19—C18—S3—O7	−69.8 (2)
S3—C18—C23—C22	176.55 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···O2ⁱ	0.98	2.53	3.426 (3)	152
C10—H10···O5ⁱⁱ	0.95	2.59	3.361 (3)	138
C14—H14···O8ⁱⁱⁱ	0.95	2.49	3.222 (3)	134
C21—H21···Cg1^iv	0.95	2.92	3.766 (9)	149

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₄O₉S₃
M_r	540.60
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	5.8962 (5), 14.6650 (14), 15.1812 (14)
α, β, γ (°)	69.164 (2), 85.096 (3), 87.685 (2)
V (Å³)	1222.28 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.21 × 0.12 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.919, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	9027, 5782, 4717
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.126, 1.03
No. of reflections	5782
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.34

Computer programs: SMART-W2K/NT (Bruker, 2003), SAINT-W2K/NT (Bruker, 2003), SAINT-W2K/NT, SHELXTL-NT (Bruker, 2003), SHELXTL-NT, ORTEP-3 for Windows (Farrugia, 1997).