Benzene-1,2,3-triyl tris­(benzene­sulfonate)

Xiao, Z.-P.; Li, H.-Q.; Shi, L.; Fang, R.-Q.; Zhu, H.-L.

doi:10.1107/S1600536807043887

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Benzene-1,2,3-triyl tris(benzenesulfonate)

Z.-P. Xiao, H.-Q. Li, L. Shi, R.-Q. Fang and H.-L. Zhu

The title compound, C₂₄H₁₈O₉S₃, crystallizes with two molecules per asymmetric unit, with distinctly different conformations, as quantified by the C-O-S-C torsion angles.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043887/hb2522sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043887/hb2522Isup2.hkl Contains datablock I

CCDC reference: 663817

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
R factor = 0.044
wR factor = 0.116
Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.89
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.97
           From the CIF: _reflns_number_total               5130
           Count of symmetry unique reflns         4843
           Completeness (_total/calc)            105.93%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       287
           Fraction of Friedel pairs measured     0.059
           Are heavy atom types Z>Si present        yes
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         49

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

   3 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Benzenesulfonates are important protecting groups (Schuda & Price, 1987) and intermediates (Andersen et al., 1982) in organic synthesis. Benzenesulfonate itself shows some biological acitivities (Linusson et al., 2001). We new report the structure of the title compound, (I), which crystallizes with two molecules in the asymmetric unit. The bond distances and angles in both molecules are normal (Allen et al., 1995)

In the C1 molecule, the three pendant benzene rings and the central benzene ring form a cage-like arrangement (Fig. 1). In the second molecule, the cage is opened because of one benzene ring (C31—C36) turned to the opposite direction. This is reflected in the different C—O—S—C torsion angles for the two molecules (Table 1).

Related literature top

For background, see: Andersen et al. (1982); Linusson et al. (2001); Schuda & Price (1987). For reference structural data, see: Allen et al. (1995).

Experimental top

Benzenesulfonyl chloride (23 ml, 180 mmol) was added dropwise to a solution of pyrogallol (6.3 g, 50 mmol) in Et₃N (80 ml) and CH₂Cl₂ (100 ml) at 273 K with stirring. After one hour, the residue was filtered, washed with petrol ether (20 ml × 3) and water (20 ml × 3) to yield the pale yellow title compound in a yield of 90%. Colorless blocks of (I) were grown by diffusion of petroleum ether into an AcOEt solution.

Structure description top

For background, see: Andersen et al. (1982); Linusson et al. (2001); Schuda & Price (1987). For reference structural data, see: Allen et al. (1995).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level (H atoms omitted for clarity).

Benzene-1,2,3-triyl tris(benzenesulfonate) top

Crystal data top

C₂₄H₁₈O₉S₃	F(000) = 1128
M_r = 546.57	D_x = 1.495 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3107 reflections
a = 8.8100 (18) Å	θ = 1.1–25.4°
b = 31.318 (6) Å	µ = 0.36 mm⁻¹
c = 9.0460 (18) Å	T = 298 K
β = 103.42 (3)°	Block, colorless
V = 2427.7 (8) Å³	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4818 independent reflections
Radiation source: fine-focus sealed tube	3932 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 26.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = 0→10
T_min = 0.932, T_max = 0.965	k = 0→38
5130 measured reflections	l = −11→10

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0547P)² + 0.956P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.115	(Δ/σ)_max = 0.001
S = 1.09	Δρ_max = 0.26 e Å⁻³
4818 reflections	Δρ_min = −0.32 e Å⁻³
650 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
49 restraints	Extinction coefficient: 0.0127 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 156 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.02 (9)

Crystal data top

C₂₄H₁₈O₉S₃	V = 2427.7 (8) Å³
M_r = 546.57	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 8.8100 (18) Å	µ = 0.36 mm⁻¹
b = 31.318 (6) Å	T = 298 K
c = 9.0460 (18) Å	0.20 × 0.20 × 0.10 mm
β = 103.42 (3)°

Data collection top

Bruker SMART CCD diffractometer	4818 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3932 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.965	R_int = 0.021
5130 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.115	Δρ_max = 0.26 e Å⁻³
S = 1.09	Δρ_min = −0.32 e Å⁻³
4818 reflections	Absolute structure: Flack (1983), 156 Friedel pairs
650 parameters	Absolute structure parameter: 0.02 (9)
49 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2796 (6)	0.97922 (17)	0.2690 (5)	0.0422 (13)
C2	0.2819 (5)	0.96220 (15)	0.4103 (5)	0.0386 (11)
C3	0.3283 (6)	0.92003 (16)	0.4382 (6)	0.0449 (13)
C4	0.3653 (7)	0.8952 (2)	0.3245 (6)	0.0550 (15)
H4	0.3934	0.8667	0.3426	0.066*
C5	0.3597 (7)	0.91325 (19)	0.1846 (7)	0.0594 (17)
H5	0.3837	0.8966	0.1079	0.071*
C6	0.3194 (7)	0.95559 (19)	0.1555 (6)	0.0526 (15)
H6	0.3192	0.9678	0.0617	0.063*
C7	−0.0573 (6)	1.01924 (16)	0.2242 (6)	0.0416 (12)
C8	−0.1279 (7)	0.98070 (17)	0.1759 (7)	0.0527 (15)
H8	−0.0956	0.9645	0.1026	0.063*
C9	−0.2480 (7)	0.9667 (2)	0.2390 (8)	0.0657 (18)
H9	−0.2992	0.9412	0.2069	0.079*
C10	−0.2912 (7)	0.9909 (2)	0.3499 (8)	0.0621 (17)
H10	−0.3720	0.9815	0.3919	0.075*
C11	−0.2178 (7)	1.02861 (19)	0.3995 (7)	0.0557 (16)
H11	−0.2478	1.0443	0.4752	0.067*
C12	−0.0996 (7)	1.04307 (18)	0.3366 (6)	0.0502 (14)
H12	−0.0487	1.0686	0.3694	0.060*
C13	0.2727 (6)	1.06295 (17)	0.6259 (5)	0.0408 (12)
C14	0.3127 (7)	1.09213 (17)	0.5274 (7)	0.0550 (15)
H14	0.3865	1.0853	0.4724	0.066*
C15	0.2417 (8)	1.1315 (2)	0.5118 (8)	0.072 (2)
H15	0.2659	1.1513	0.4445	0.086*
C16	0.1348 (8)	1.1414 (2)	0.5956 (8)	0.075 (2)
H16	0.0869	1.1681	0.5840	0.090*
C17	0.0975 (8)	1.1125 (2)	0.6964 (8)	0.073 (2)
H17	0.0262	1.1198	0.7535	0.087*
C18	0.1669 (7)	1.07252 (19)	0.7122 (7)	0.0568 (16)
H18	0.1427	1.0526	0.7795	0.068*
C19	0.0667 (6)	0.89228 (17)	0.6361 (6)	0.0474 (13)
C20	−0.0660 (6)	0.87825 (19)	0.5367 (7)	0.0556 (15)
H20	−0.0606	0.8578	0.4635	0.067*
C21	−0.2081 (7)	0.8951 (2)	0.5475 (8)	0.0647 (17)
H21	−0.2992	0.8859	0.4808	0.078*
C22	−0.2156 (7)	0.9250 (2)	0.6556 (7)	0.0684 (18)
H22	−0.3121	0.9352	0.6648	0.082*
C23	−0.0816 (7)	0.9401 (2)	0.7509 (7)	0.072 (2)
H23	−0.0872	0.9616	0.8203	0.086*
C24	0.0621 (7)	0.9233 (2)	0.7433 (7)	0.0605 (17)
H24	0.1534	0.9327	0.8091	0.073*
C25	0.5994 (6)	0.78725 (16)	0.8570 (5)	0.0423 (13)
C26	0.6434 (7)	0.80936 (18)	0.7417 (6)	0.0497 (14)
H26	0.6764	0.8376	0.7563	0.060*
C27	0.6383 (7)	0.78949 (18)	0.6056 (6)	0.0535 (15)
H27	0.6686	0.8046	0.5287	0.064*
C28	0.5895 (7)	0.74777 (17)	0.5794 (6)	0.0472 (13)
H28	0.5875	0.7345	0.4870	0.057*
C29	0.5436 (6)	0.72644 (16)	0.6953 (5)	0.0390 (12)
C30	0.5464 (6)	0.74536 (15)	0.8328 (5)	0.0364 (11)
C31	0.8991 (6)	0.81516 (17)	1.1089 (6)	0.0512 (14)
C32	1.0032 (8)	0.8323 (2)	1.0314 (8)	0.0697 (19)
H32	0.9755	0.8556	0.9670	0.084*
C33	1.1494 (8)	0.8140 (3)	1.0523 (10)	0.086 (3)
H33	1.2217	0.8253	1.0029	0.104*
C34	1.1887 (9)	0.7792 (3)	1.1452 (9)	0.088 (3)
H34	1.2871	0.7670	1.1578	0.106*
C35	1.0832 (8)	0.7622 (3)	1.2198 (8)	0.080 (2)
H35	1.1104	0.7385	1.2824	0.096*
C36	0.9368 (7)	0.78024 (19)	1.2019 (7)	0.0601 (16)
H36	0.8650	0.7689	1.2521	0.072*
C37	0.5128 (6)	0.64779 (17)	1.0596 (5)	0.0427 (12)
C38	0.4055 (7)	0.6402 (2)	1.1456 (7)	0.0577 (16)
H38	0.3805	0.6613	1.2084	0.069*
C39	0.3362 (9)	0.6005 (2)	1.1361 (9)	0.080 (2)
H39	0.2634	0.5947	1.1932	0.096*
C40	0.3736 (9)	0.5696 (2)	1.0433 (9)	0.082 (2)
H40	0.3257	0.5430	1.0377	0.098*
C41	0.4813 (9)	0.5776 (2)	0.9586 (8)	0.075 (2)
H41	0.5063	0.5565	0.8960	0.090*
C42	0.5522 (7)	0.61703 (18)	0.9665 (7)	0.0571 (16)
H42	0.6255	0.6227	0.9098	0.068*
C43	0.1977 (6)	0.69222 (15)	0.6702 (5)	0.0394 (12)
C44	0.1502 (6)	0.73387 (16)	0.6415 (6)	0.0488 (14)
H44	0.1898	0.7505	0.5741	0.059*
C45	0.0424 (7)	0.7504 (2)	0.7151 (7)	0.0598 (17)
H45	0.0082	0.7784	0.6965	0.072*
C46	−0.0147 (7)	0.7257 (2)	0.8159 (7)	0.0609 (17)
H46	−0.0878	0.7370	0.8646	0.073*
C47	0.0361 (7)	0.6843 (2)	0.8446 (7)	0.0588 (17)
H47	−0.0024	0.6679	0.9132	0.071*
C48	0.1439 (7)	0.66703 (19)	0.7725 (6)	0.0507 (14)
H48	0.1793	0.6392	0.7924	0.061*
O1	0.2479 (4)	1.02316 (13)	0.2505 (4)	0.0481 (10)
O2	0.2327 (4)	0.98597 (12)	0.5206 (4)	0.0436 (9)
O3	0.3503 (4)	0.90587 (14)	0.5870 (5)	0.0548 (10)
O4	0.0723 (5)	1.01793 (18)	−0.0037 (5)	0.0674 (12)
O5	0.0995 (6)	1.08356 (15)	0.1488 (6)	0.0724 (13)
O6	0.5018 (4)	1.01278 (16)	0.5969 (5)	0.0618 (12)
O7	0.3547 (6)	0.99497 (14)	0.7888 (4)	0.0620 (12)
O8	0.2226 (6)	0.83636 (16)	0.5216 (7)	0.0864 (16)
O9	0.3271 (6)	0.8596 (2)	0.7861 (6)	0.0960 (19)
O10	0.5939 (5)	0.80350 (13)	0.9990 (4)	0.0519 (10)
O11	0.4876 (4)	0.72388 (13)	0.9426 (4)	0.0423 (9)
O12	0.4998 (4)	0.68312 (12)	0.6795 (4)	0.0432 (9)
O13	0.7046 (6)	0.87594 (15)	0.9994 (6)	0.0819 (15)
O14	0.6723 (6)	0.84022 (18)	1.2304 (5)	0.0802 (15)
O15	0.7514 (4)	0.69465 (15)	1.0327 (5)	0.0612 (12)
O16	0.5972 (6)	0.71699 (15)	1.2124 (4)	0.0651 (12)
O17	0.3137 (5)	0.69192 (15)	0.4325 (4)	0.0594 (11)
O18	0.3319 (5)	0.62518 (13)	0.5817 (5)	0.0642 (12)
S1	0.08707 (18)	1.03852 (5)	0.13813 (17)	0.0502 (4)
S2	0.35990 (15)	1.01224 (5)	0.64660 (15)	0.0432 (3)
S3	0.2467 (2)	0.86794 (5)	0.6354 (2)	0.0633 (4)
S4	0.71387 (19)	0.83832 (5)	1.08912 (19)	0.0580 (4)
S5	0.60581 (15)	0.69739 (5)	1.07434 (14)	0.0426 (3)
S6	0.33127 (17)	0.67046 (5)	0.57364 (16)	0.0454 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.029 (3)	0.048 (3)	0.050 (3)	−0.006 (2)	0.012 (2)	−0.004 (3)
C2	0.027 (2)	0.042 (3)	0.048 (3)	−0.006 (2)	0.013 (2)	−0.008 (2)
C3	0.032 (3)	0.047 (3)	0.054 (3)	−0.005 (2)	0.008 (2)	−0.005 (3)
C4	0.044 (3)	0.052 (4)	0.068 (4)	0.003 (3)	0.011 (3)	−0.010 (3)
C5	0.049 (3)	0.066 (4)	0.066 (4)	0.003 (3)	0.017 (3)	−0.025 (3)
C6	0.042 (3)	0.073 (4)	0.045 (3)	−0.001 (3)	0.014 (2)	−0.006 (3)
C7	0.036 (3)	0.045 (3)	0.044 (3)	−0.001 (2)	0.011 (2)	0.007 (2)
C8	0.057 (4)	0.045 (3)	0.061 (4)	−0.003 (3)	0.025 (3)	−0.010 (3)
C9	0.060 (4)	0.055 (4)	0.091 (5)	−0.010 (3)	0.034 (4)	−0.006 (4)
C10	0.047 (4)	0.064 (4)	0.085 (5)	−0.003 (3)	0.033 (3)	0.007 (4)
C11	0.053 (4)	0.058 (4)	0.061 (4)	0.012 (3)	0.023 (3)	0.004 (3)
C12	0.052 (3)	0.043 (3)	0.055 (3)	0.000 (3)	0.012 (3)	−0.003 (3)
C13	0.036 (3)	0.045 (3)	0.040 (3)	−0.006 (2)	0.008 (2)	−0.006 (2)
C14	0.056 (4)	0.048 (4)	0.062 (4)	−0.013 (3)	0.018 (3)	−0.001 (3)
C15	0.073 (5)	0.054 (4)	0.079 (5)	−0.016 (4)	0.000 (4)	0.008 (4)
C16	0.067 (5)	0.056 (4)	0.086 (5)	0.006 (4)	−0.017 (4)	−0.011 (4)
C17	0.061 (4)	0.084 (6)	0.073 (5)	0.021 (4)	0.016 (4)	−0.019 (4)
C18	0.062 (4)	0.062 (4)	0.051 (3)	0.009 (3)	0.022 (3)	−0.001 (3)
C19	0.041 (3)	0.048 (3)	0.050 (3)	−0.003 (3)	0.006 (2)	0.008 (3)
C20	0.063 (4)	0.045 (3)	0.054 (3)	−0.004 (3)	0.004 (3)	−0.003 (3)
C21	0.049 (4)	0.059 (4)	0.079 (4)	−0.004 (3)	0.000 (3)	−0.001 (3)
C22	0.052 (4)	0.076 (5)	0.079 (5)	0.003 (4)	0.019 (3)	0.009 (4)
C23	0.090 (5)	0.074 (5)	0.060 (4)	0.002 (4)	0.033 (4)	−0.013 (4)
C24	0.056 (4)	0.072 (4)	0.051 (3)	−0.011 (3)	0.006 (3)	−0.006 (3)
C25	0.035 (3)	0.053 (4)	0.037 (3)	0.007 (2)	0.004 (2)	−0.006 (2)
C26	0.054 (3)	0.035 (3)	0.059 (4)	−0.002 (3)	0.011 (3)	0.003 (3)
C27	0.054 (3)	0.064 (4)	0.046 (3)	0.000 (3)	0.018 (3)	0.016 (3)
C28	0.050 (3)	0.053 (4)	0.039 (3)	−0.001 (3)	0.013 (2)	−0.002 (2)
C29	0.038 (3)	0.039 (3)	0.041 (3)	0.003 (2)	0.011 (2)	−0.002 (2)
C30	0.031 (3)	0.042 (3)	0.036 (3)	0.010 (2)	0.007 (2)	0.007 (2)
C31	0.049 (3)	0.050 (4)	0.051 (3)	0.000 (3)	0.005 (3)	−0.012 (3)
C32	0.077 (5)	0.060 (4)	0.075 (5)	−0.018 (4)	0.024 (4)	−0.007 (4)
C33	0.063 (5)	0.100 (7)	0.103 (6)	−0.022 (5)	0.035 (4)	−0.032 (5)
C34	0.053 (4)	0.108 (7)	0.095 (6)	0.003 (5)	0.002 (4)	−0.032 (5)
C35	0.082 (5)	0.078 (5)	0.067 (4)	0.021 (4)	−0.007 (4)	−0.002 (4)
C36	0.060 (4)	0.065 (4)	0.053 (3)	0.001 (3)	0.009 (3)	0.004 (3)
C37	0.043 (3)	0.047 (3)	0.037 (3)	0.003 (3)	0.007 (2)	0.004 (2)
C38	0.054 (4)	0.067 (4)	0.057 (4)	−0.007 (3)	0.022 (3)	0.006 (3)
C39	0.063 (4)	0.088 (6)	0.086 (5)	−0.020 (4)	0.011 (4)	0.018 (5)
C40	0.077 (5)	0.047 (4)	0.098 (6)	−0.015 (4)	−0.025 (4)	0.018 (4)
C41	0.090 (6)	0.045 (4)	0.074 (5)	0.010 (4)	−0.014 (4)	−0.011 (3)
C42	0.060 (4)	0.059 (4)	0.050 (3)	0.016 (3)	0.008 (3)	−0.002 (3)
C43	0.037 (3)	0.042 (3)	0.039 (3)	−0.002 (2)	0.007 (2)	−0.008 (2)
C44	0.048 (3)	0.046 (3)	0.055 (3)	0.002 (3)	0.019 (3)	−0.001 (3)
C45	0.054 (4)	0.055 (4)	0.074 (4)	0.010 (3)	0.022 (3)	−0.005 (3)
C46	0.045 (3)	0.072 (5)	0.073 (4)	−0.001 (3)	0.027 (3)	−0.016 (4)
C47	0.051 (4)	0.069 (4)	0.061 (4)	−0.016 (3)	0.024 (3)	0.000 (3)
C48	0.055 (4)	0.049 (3)	0.049 (3)	−0.005 (3)	0.014 (3)	0.001 (3)
O1	0.040 (2)	0.056 (3)	0.049 (2)	−0.0062 (18)	0.0113 (17)	−0.0005 (19)
O2	0.0356 (19)	0.054 (2)	0.0437 (19)	−0.0046 (17)	0.0146 (16)	−0.0118 (17)
O3	0.040 (2)	0.060 (3)	0.062 (3)	0.0002 (19)	0.0061 (18)	0.006 (2)
O4	0.066 (3)	0.097 (4)	0.043 (2)	−0.011 (3)	0.020 (2)	0.010 (2)
O5	0.073 (3)	0.053 (3)	0.095 (3)	−0.006 (2)	0.027 (3)	0.025 (2)
O6	0.033 (2)	0.076 (3)	0.078 (3)	−0.002 (2)	0.0172 (19)	−0.024 (2)
O7	0.083 (3)	0.057 (3)	0.042 (2)	0.000 (2)	0.007 (2)	0.002 (2)
O8	0.088 (4)	0.051 (3)	0.133 (5)	−0.003 (3)	0.050 (3)	−0.017 (3)
O9	0.069 (3)	0.117 (5)	0.100 (4)	0.027 (3)	0.016 (3)	0.061 (4)
O10	0.056 (2)	0.052 (2)	0.047 (2)	0.0027 (19)	0.0097 (18)	−0.0092 (19)
O11	0.038 (2)	0.049 (2)	0.043 (2)	0.0048 (17)	0.0151 (16)	0.0050 (17)
O12	0.041 (2)	0.043 (2)	0.046 (2)	0.0035 (17)	0.0112 (16)	−0.0060 (16)
O13	0.098 (4)	0.045 (3)	0.091 (3)	0.012 (3)	−0.003 (3)	−0.009 (2)
O14	0.076 (3)	0.096 (4)	0.066 (3)	0.011 (3)	0.013 (2)	−0.041 (3)
O15	0.039 (2)	0.079 (3)	0.068 (3)	0.006 (2)	0.0169 (19)	0.021 (2)
O16	0.092 (3)	0.059 (3)	0.042 (2)	−0.013 (2)	0.011 (2)	−0.0043 (19)
O17	0.064 (3)	0.071 (3)	0.044 (2)	0.005 (2)	0.0125 (19)	−0.007 (2)
O18	0.069 (3)	0.041 (2)	0.085 (3)	−0.003 (2)	0.022 (2)	−0.020 (2)
S1	0.0505 (8)	0.0540 (9)	0.0484 (8)	−0.0048 (7)	0.0160 (7)	0.0123 (7)
S2	0.0375 (7)	0.0471 (8)	0.0446 (7)	−0.0002 (6)	0.0091 (6)	−0.0057 (6)
S3	0.0542 (9)	0.0539 (10)	0.0823 (11)	0.0079 (7)	0.0171 (8)	0.0175 (9)
S4	0.0629 (10)	0.0482 (9)	0.0586 (9)	0.0092 (8)	0.0051 (8)	−0.0169 (7)
S5	0.0408 (7)	0.0524 (9)	0.0346 (6)	−0.0024 (6)	0.0087 (5)	0.0025 (6)
S6	0.0471 (8)	0.0456 (8)	0.0444 (7)	0.0016 (6)	0.0125 (6)	−0.0107 (6)

Geometric parameters (Å, º) top

C1—C6	1.375 (6)	C29—C30	1.373 (5)
C1—C2	1.381 (5)	C29—O12	1.409 (6)
C1—O1	1.406 (7)	C30—O11	1.395 (6)
C2—C3	1.388 (6)	C31—C36	1.373 (6)
C2—O2	1.392 (6)	C31—C32	1.385 (6)
C3—C4	1.387 (6)	C31—S4	1.757 (6)
C3—O3	1.388 (6)	C32—C33	1.383 (7)
C4—C5	1.377 (6)	C32—H32	0.9300
C4—H4	0.9300	C33—C34	1.370 (7)
C5—C6	1.382 (6)	C33—H33	0.9300
C5—H5	0.9300	C34—C35	1.376 (7)
C6—H6	0.9300	C34—H34	0.9300
C7—C12	1.381 (6)	C35—C36	1.383 (6)
C7—C8	1.382 (6)	C35—H35	0.9300
C7—S1	1.745 (5)	C36—H36	0.9300
C8—C9	1.385 (6)	C37—C42	1.376 (6)
C8—H8	0.9300	C37—C38	1.377 (6)
C9—C10	1.379 (6)	C37—S5	1.747 (6)
C9—H9	0.9300	C38—C39	1.378 (6)
C10—C11	1.370 (6)	C38—H38	0.9300
C10—H10	0.9300	C39—C40	1.372 (7)
C11—C12	1.374 (6)	C39—H39	0.9300
C11—H11	0.9300	C40—C41	1.375 (7)
C12—H12	0.9300	C40—H40	0.9300
C13—C14	1.378 (6)	C41—C42	1.378 (6)
C13—C18	1.381 (6)	C41—H41	0.9300
C13—S2	1.755 (5)	C42—H42	0.9300
C14—C15	1.374 (6)	C43—C44	1.376 (6)
C14—H14	0.9300	C43—C48	1.381 (6)
C15—C16	1.375 (7)	C43—S6	1.757 (5)
C15—H15	0.9300	C44—C45	1.381 (6)
C16—C17	1.377 (7)	C44—H44	0.9300
C16—H16	0.9300	C45—C46	1.377 (6)
C17—C18	1.387 (6)	C45—H45	0.9300
C17—H17	0.9300	C46—C47	1.376 (6)
C18—H18	0.9300	C46—H46	0.9300
C19—C20	1.371 (6)	C47—C48	1.381 (6)
C19—C24	1.380 (6)	C47—H47	0.9300
C19—S3	1.761 (6)	C48—H48	0.9300
C20—C21	1.382 (6)	O1—S1	1.614 (4)
C20—H20	0.9300	O2—S2	1.624 (4)
C21—C22	1.368 (6)	O3—S3	1.619 (4)
C21—H21	0.9300	O4—S1	1.415 (5)
C22—C23	1.374 (6)	O5—S1	1.416 (5)
C22—H22	0.9300	O6—S2	1.423 (4)
C23—C24	1.388 (6)	O7—S2	1.406 (4)
C23—H23	0.9300	O8—S3	1.407 (6)
C24—H24	0.9300	O9—S3	1.408 (5)
C25—C26	1.380 (6)	O10—S4	1.603 (4)
C25—O10	1.392 (6)	O11—S5	1.618 (4)
C25—C30	1.393 (6)	O12—S6	1.618 (4)
C26—C27	1.371 (6)	O13—S4	1.422 (5)
C26—H26	0.9300	O14—S4	1.410 (5)
C27—C28	1.379 (6)	O15—S5	1.421 (4)
C27—H27	0.9300	O16—S5	1.409 (4)
C28—C29	1.380 (6)	O17—S6	1.419 (4)
C28—H28	0.9300	O18—S6	1.420 (4)

C6—C1—C2	122.1 (5)	C33—C32—C31	118.3 (7)
C6—C1—O1	121.0 (5)	C33—C32—H32	120.8
C2—C1—O1	116.6 (4)	C31—C32—H32	120.8
C1—C2—C3	118.4 (5)	C34—C33—C32	120.6 (7)
C1—C2—O2	121.1 (4)	C34—C33—H33	119.7
C3—C2—O2	120.4 (4)	C32—C33—H33	119.7
C4—C3—O3	122.4 (5)	C33—C34—C35	120.3 (7)
C4—C3—C2	120.6 (5)	C33—C34—H34	119.8
O3—C3—C2	116.7 (4)	C35—C34—H34	119.8
C5—C4—C3	119.2 (6)	C34—C35—C36	120.2 (7)
C5—C4—H4	120.4	C34—C35—H35	119.9
C3—C4—H4	120.4	C36—C35—H35	119.9
C4—C5—C6	121.4 (5)	C31—C36—C35	118.9 (6)
C4—C5—H5	119.3	C31—C36—H36	120.5
C6—C5—H5	119.3	C35—C36—H36	120.5
C1—C6—C5	118.2 (5)	C42—C37—C38	121.9 (6)
C1—C6—H6	120.9	C42—C37—S5	119.3 (4)
C5—C6—H6	120.9	C38—C37—S5	118.8 (4)
C12—C7—C8	121.8 (5)	C37—C38—C39	118.2 (6)
C12—C7—S1	119.4 (4)	C37—C38—H38	120.9
C8—C7—S1	118.9 (4)	C39—C38—H38	120.9
C7—C8—C9	118.4 (5)	C40—C39—C38	120.6 (7)
C7—C8—H8	120.8	C40—C39—H39	119.7
C9—C8—H8	120.8	C38—C39—H39	119.7
C10—C9—C8	119.5 (6)	C39—C40—C41	120.5 (7)
C10—C9—H9	120.2	C39—C40—H40	119.8
C8—C9—H9	120.2	C41—C40—H40	119.8
C11—C10—C9	121.5 (6)	C40—C41—C42	119.9 (6)
C11—C10—H10	119.3	C40—C41—H41	120.1
C9—C10—H10	119.3	C42—C41—H41	120.1
C10—C11—C12	119.6 (6)	C37—C42—C41	118.9 (6)
C10—C11—H11	120.2	C37—C42—H42	120.6
C12—C11—H11	120.2	C41—C42—H42	120.6
C11—C12—C7	119.1 (5)	C44—C43—C48	122.1 (5)
C11—C12—H12	120.4	C44—C43—S6	118.9 (4)
C7—C12—H12	120.4	C48—C43—S6	119.0 (4)
C14—C13—C18	121.9 (5)	C43—C44—C45	118.6 (5)
C14—C13—S2	119.9 (4)	C43—C44—H44	120.7
C18—C13—S2	118.2 (4)	C45—C44—H44	120.7
C15—C14—C13	118.9 (6)	C46—C45—C44	120.4 (6)
C15—C14—H14	120.6	C46—C45—H45	119.8
C13—C14—H14	120.6	C44—C45—H45	119.8
C14—C15—C16	120.0 (6)	C47—C46—C45	120.1 (6)
C14—C15—H15	120.0	C47—C46—H46	120.0
C16—C15—H15	120.0	C45—C46—H46	120.0
C15—C16—C17	121.0 (7)	C46—C47—C48	120.7 (6)
C15—C16—H16	119.5	C46—C47—H47	119.7
C17—C16—H16	119.5	C48—C47—H47	119.7
C16—C17—C18	119.7 (6)	C47—C48—C43	118.2 (5)
C16—C17—H17	120.2	C47—C48—H48	120.9
C18—C17—H17	120.2	C43—C48—H48	120.9
C13—C18—C17	118.5 (6)	C1—O1—S1	119.2 (3)
C13—C18—H18	120.8	C2—O2—S2	119.7 (3)
C17—C18—H18	120.8	C3—O3—S3	122.4 (3)
C20—C19—C24	121.8 (5)	C25—O10—S4	123.9 (4)
C20—C19—S3	119.4 (4)	C30—O11—S5	119.4 (3)
C24—C19—S3	118.7 (4)	C29—O12—S6	119.2 (3)
C19—C20—C21	118.7 (5)	O4—S1—O5	120.3 (3)
C19—C20—H20	120.7	O4—S1—O1	108.5 (3)
C21—C20—H20	120.7	O5—S1—O1	102.2 (3)
C22—C21—C20	120.4 (6)	O4—S1—C7	108.9 (3)
C22—C21—H21	119.8	O5—S1—C7	111.5 (3)
C20—C21—H21	119.8	O1—S1—C7	103.9 (2)
C21—C22—C23	120.5 (6)	O7—S2—O6	120.7 (3)
C21—C22—H22	119.7	O7—S2—O2	106.4 (2)
C23—C22—H22	119.7	O6—S2—O2	107.3 (2)
C22—C23—C24	119.9 (6)	O7—S2—C13	109.8 (3)
C22—C23—H23	120.0	O6—S2—C13	110.5 (3)
C24—C23—H23	120.0	O2—S2—C13	99.8 (2)
C19—C24—C23	118.6 (6)	O8—S3—O9	122.3 (4)
C19—C24—H24	120.7	O8—S3—O3	108.5 (3)
C23—C24—H24	120.7	O9—S3—O3	102.1 (3)
C26—C25—O10	126.1 (5)	O8—S3—C19	108.9 (3)
C26—C25—C30	119.8 (5)	O9—S3—C19	109.1 (3)
O10—C25—C30	114.0 (4)	O3—S3—C19	104.4 (2)
C27—C26—C25	119.6 (5)	O14—S4—O13	119.3 (3)
C27—C26—H26	120.2	O14—S4—O10	102.1 (3)
C25—C26—H26	120.2	O13—S4—O10	109.2 (3)
C26—C27—C28	121.9 (5)	O14—S4—C31	110.9 (3)
C26—C27—H27	119.0	O13—S4—C31	109.2 (3)
C28—C27—H27	119.0	O10—S4—C31	105.0 (2)
C27—C28—C29	117.5 (5)	O16—S5—O15	119.9 (3)
C27—C28—H28	121.2	O16—S5—O11	105.8 (3)
C29—C28—H28	121.2	O15—S5—O11	107.6 (2)
C30—C29—C28	122.2 (5)	O16—S5—C37	109.5 (2)
C30—C29—O12	117.0 (4)	O15—S5—C37	111.2 (3)
C28—C29—O12	120.7 (4)	O11—S5—C37	100.9 (2)
C29—C30—C25	118.9 (5)	O17—S6—O18	121.2 (3)
C29—C30—O11	120.4 (4)	O17—S6—O12	108.0 (2)
C25—C30—O11	120.6 (4)	O18—S6—O12	102.8 (3)
C36—C31—C32	121.7 (6)	O17—S6—C43	108.5 (2)
C36—C31—S4	118.5 (4)	O18—S6—C43	110.9 (3)
C32—C31—S4	119.8 (5)	O12—S6—C43	103.9 (2)

C6—C1—C2—C3	1.0 (7)	C44—C45—C46—C47	0.4 (10)
O1—C1—C2—C3	−173.5 (4)	C45—C46—C47—C48	−0.4 (10)
C6—C1—C2—O2	−176.4 (5)	C46—C47—C48—C43	−0.6 (9)
O1—C1—C2—O2	9.2 (7)	C44—C43—C48—C47	1.6 (8)
C1—C2—C3—C4	−2.6 (7)	S6—C43—C48—C47	−178.5 (5)
O2—C2—C3—C4	174.8 (5)	C6—C1—O1—S1	72.7 (6)
C1—C2—C3—O3	171.2 (4)	C2—C1—O1—S1	−112.8 (4)
O2—C2—C3—O3	−11.5 (7)	C1—C2—O2—S2	−94.4 (5)
O3—C3—C4—C5	−171.5 (5)	C3—C2—O2—S2	88.3 (5)
C2—C3—C4—C5	1.9 (8)	C4—C3—O3—S3	−69.1 (6)
C3—C4—C5—C6	0.5 (9)	C2—C3—O3—S3	117.3 (5)
C2—C1—C6—C5	1.3 (8)	C26—C25—O10—S4	−34.4 (7)
O1—C1—C6—C5	175.5 (5)	C30—C25—O10—S4	149.2 (4)
C4—C5—C6—C1	−2.1 (9)	C29—C30—O11—S5	95.4 (5)
C12—C7—C8—C9	2.4 (9)	C25—C30—O11—S5	−88.7 (5)
S1—C7—C8—C9	−176.6 (5)	C30—C29—O12—S6	108.0 (5)
C7—C8—C9—C10	−1.5 (10)	C28—C29—O12—S6	−75.3 (6)
C8—C9—C10—C11	−0.1 (11)	C1—O1—S1—O4	−51.2 (4)
C9—C10—C11—C12	0.8 (11)	C1—O1—S1—O5	−179.3 (4)
C10—C11—C12—C7	0.1 (9)	C1—O1—S1—C7	64.6 (4)
C8—C7—C12—C11	−1.7 (9)	C12—C7—S1—O4	−159.5 (5)
S1—C7—C12—C11	177.3 (5)	C8—C7—S1—O4	19.6 (6)
C18—C13—C14—C15	−1.8 (9)	C12—C7—S1—O5	−24.3 (6)
S2—C13—C14—C15	179.3 (5)	C8—C7—S1—O5	154.7 (5)
C13—C14—C15—C16	1.1 (10)	C12—C7—S1—O1	85.0 (5)
C14—C15—C16—C17	0.3 (11)	C8—C7—S1—O1	−96.0 (5)
C15—C16—C17—C18	−1.0 (11)	C2—O2—S2—O7	−118.0 (4)
C14—C13—C18—C17	1.1 (9)	C2—O2—S2—O6	12.6 (4)
S2—C13—C18—C17	−180.0 (5)	C2—O2—S2—C13	127.8 (4)
C16—C17—C18—C13	0.3 (10)	C14—C13—S2—O7	156.0 (5)
C24—C19—C20—C21	−1.6 (9)	C18—C13—S2—O7	−22.9 (5)
S3—C19—C20—C21	174.4 (5)	C14—C13—S2—O6	20.4 (5)
C19—C20—C21—C22	−0.2 (10)	C18—C13—S2—O6	−158.5 (4)
C20—C21—C22—C23	2.7 (11)	C14—C13—S2—O2	−92.4 (5)
C21—C22—C23—C24	−3.6 (11)	C18—C13—S2—O2	88.7 (5)
C20—C19—C24—C23	0.8 (10)	C3—O3—S3—O8	39.5 (5)
S3—C19—C24—C23	−175.3 (5)	C3—O3—S3—O9	169.9 (4)
C22—C23—C24—C19	1.8 (10)	C3—O3—S3—C19	−76.5 (4)
O10—C25—C26—C27	−177.9 (5)	C20—C19—S3—O8	1.4 (6)
C30—C25—C26—C27	−1.7 (8)	C24—C19—S3—O8	177.6 (5)
C25—C26—C27—C28	0.3 (9)	C20—C19—S3—O9	−134.4 (5)
C26—C27—C28—C29	0.7 (9)	C24—C19—S3—O9	41.8 (6)
C27—C28—C29—C30	−0.3 (8)	C20—C19—S3—O3	117.1 (5)
C27—C28—C29—O12	−176.8 (5)	C24—C19—S3—O3	−66.7 (5)
C28—C29—C30—C25	−1.0 (8)	C25—O10—S4—O14	−173.2 (4)
O12—C29—C30—C25	175.6 (4)	C25—O10—S4—O13	59.5 (5)
C28—C29—C30—O11	174.9 (5)	C25—O10—S4—C31	−57.5 (5)
O12—C29—C30—O11	−8.5 (7)	C36—C31—S4—O14	41.4 (6)
C26—C25—C30—C29	2.0 (8)	C32—C31—S4—O14	−138.4 (5)
O10—C25—C30—C29	178.7 (4)	C36—C31—S4—O13	174.9 (5)
C26—C25—C30—O11	−173.9 (5)	C32—C31—S4—O13	−5.0 (6)
O10—C25—C30—O11	2.7 (7)	C36—C31—S4—O10	−68.1 (5)
C36—C31—C32—C33	−1.4 (10)	C32—C31—S4—O10	112.0 (5)
S4—C31—C32—C33	178.5 (5)	C30—O11—S5—O16	117.9 (4)
C31—C32—C33—C34	1.2 (11)	C30—O11—S5—O15	−11.3 (4)
C32—C33—C34—C35	−0.4 (12)	C30—O11—S5—C37	−128.0 (4)
C33—C34—C35—C36	−0.2 (12)	C42—C37—S5—O16	−157.0 (5)
C32—C31—C36—C35	0.8 (9)	C38—C37—S5—O16	20.9 (5)
S4—C31—C36—C35	−179.1 (5)	C42—C37—S5—O15	−22.1 (5)
C34—C35—C36—C31	0.0 (11)	C38—C37—S5—O15	155.8 (4)
C42—C37—C38—C39	−0.3 (9)	C42—C37—S5—O11	91.7 (5)
S5—C37—C38—C39	−178.2 (5)	C38—C37—S5—O11	−90.3 (5)
C37—C38—C39—C40	0.0 (11)	C29—O12—S6—O17	48.9 (4)
C38—C39—C40—C41	0.2 (12)	C29—O12—S6—O18	178.1 (3)
C39—C40—C41—C42	−0.1 (11)	C29—O12—S6—C43	−66.2 (4)
C38—C37—C42—C41	0.4 (9)	C44—C43—S6—O17	−27.4 (5)
S5—C37—C42—C41	178.3 (5)	C48—C43—S6—O17	152.7 (4)
C40—C41—C42—C37	−0.2 (10)	C44—C43—S6—O18	−162.8 (4)
C48—C43—C44—C45	−1.6 (9)	C48—C43—S6—O18	17.3 (5)
S6—C43—C44—C45	178.5 (5)	C44—C43—S6—O12	87.4 (5)
C43—C44—C45—C46	0.6 (10)	C48—C43—S6—O12	−92.5 (5)

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈O₉S₃
M_r	546.57
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	8.8100 (18), 31.318 (6), 9.0460 (18)
β (°)	103.42 (3)
V (Å³)	2427.7 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.932, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	5130, 4818, 3932
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.115, 1.09
No. of reflections	4818
No. of parameters	650
No. of restraints	49
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.32
Absolute structure	Flack (1983), 156 Friedel pairs
Absolute structure parameter	0.02 (9)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

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