9,10-Dioxoanthracene-1,4-diyl bis­(4-methyl­benzene­sulfonate)

Teerawatananond, T.; Kerdsamut, C.; Kokpol, S.; Muangsin, N.

doi:10.1107/S1600536812015814

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1423-o1424

doi:10.1107/S1600536812015814

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9,10-Dioxoanthracene-1,4-diyl bis(4-methylbenzenesulfonate)

Thapong Teerawatananond,^a Chiaranan Kerdsamut,^b Sirirat Kokpol ^c and Nongnuj Muangsin ^d ^*

^aResearch Centre for Bioorganic Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand, ^bProgram of Bachelor of Science in Applied Chemistry (BSAC), Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand, ^cComputational Chemistry Unit Cell, Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand, and ^dCenter of Petroleum, Petrochemicals and Advanced Materials, Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand
^*Correspondence e-mail: nongnuj.j@chula.ac.th

(Received 20 March 2012; accepted 11 April 2012; online 18 April 2012)

The title molecule, C₂₈H₂₀O₈S₂, has a T-shaped conformation. The central 9,10-anthraquinone moiety is bow-shaped with the two outer aromatic rings being inclined to one another by 13.99 (11)°. The benzenesulfonate rings are inclined to one another by 47.35 (12)°, and by 34.51 (11) and 17.88 (11)° to the bridging aromatic ring of the 9,10-anthraquinone moiety. In the crystal, C—H⋯O interactions link the molecules into ribbons in [100].

Related literature

For background to the structures of anthraquinones and their biological activity, see: Zielske (1987 ); Yatsenko et al. (2000 ); Huang et al. (2004 ); Meng et al. (2005 ); García-Sosa et al. (2006 ); Cho et al. (2006 ); Carland et al. (2010 ). For related structures, see: Swaminathan & Nigam (1967 ); Cao et al. (2007 ).

Experimental

Crystal data

C₂₈H₂₀O₈S₂
M_r = 548.56
Triclinic, $[P \overline 1]$
a = 9.6796 (2) Å
b = 10.9426 (3) Å
c = 13.1833 (4) Å
α = 111.122 (1)°
β = 90.961 (1)°
γ = 107.190 (1)°
V = 1232.41 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.35 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.912, T_max = 0.948
12983 measured reflections
5616 independent reflections
3997 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.127
S = 1.02
5616 reflections
343 parameters
346 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O4ⁱ	0.93	2.48	3.333 (3)	153
C3—H3⋯O8ⁱⁱ	0.93	2.49	3.245 (3)	139
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812015814/cv5268sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015814/cv5268Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812015814/cv5268Isup3.cml

checkCIF report

Comment top

Anthraquinone and its derivatives have been studies in the many fields, for example, antimicrobial and antibiotic activity (García-Sosa et al., 2006), anticancer agents (Huang, et al., 2004; Carland et al., 2010). Additionally, both of unsubstituted and substituted anthraquinone play an important role in various photochemical and colorimetric sensor systems (Cho et al., 2006). The natural extracts or synthetic anthraquinones have been used in the field of dyes and pigments (Meng et al., 2005; Yatsenko et al., 2000; Cao et al., 2007).

1,4-Bis(hydroxy)anthraquinone is one of an important anthraquinone starting materials for preparation the various anthraquinone dyes and pigments (Zielske, 1987). In this work, we report the intermediate of an anthraquinone dye with the two symmetric tosylate substituents.

The molecular structure of 1,4-bis(tosyloxy)anthraquinone consisting of the two tosylate groups substituted at 1,4-positions of anthraquinone core, has a dragonfly-like conformation with the stranded 9,10-anthraquinone fragment. The anthraquinone plane is distorted by 0.1814 Å from the mean plane defined by 16 atoms becuase of the steric effect of two substitued tosyl groups. The O1 and O2 atoms were deviatated from the anthraquinone mean plane with the distances of -0.2736 (16) Å and -0.1467 (15) Å, respectively, which are respectively in the normal range for the distortion of oxyquinone reported for 1,4-bis(hydroxy)anthraquinone (Swaminathan et al., 1967). Additionally, the moderate intermolecular hydrogen bonds of sp²C—H···O have been investigated between the hydrogen atom bound the aromatic carbon inside quinone ring, and the oxygen atom at the sulfonate group in the p-toluenesulfonate moiety as Figure 2. The distance of C(7)—H(7)···O(4) is 3.333 (3) Å and C(3)—H(3)···O(8) is 3.245 (3) Å that showed in the Table 1. In the crystal structure, non-classical intermolecular C—H···O hydrogen bonds link molecules into ribbons in [100].

Related literature top

For background to the structures of anthraquinones and their biological activity, see: Zielske (1987); Yatsenko et al. (2000); Huang et al. (2004); Meng et al. (2005); García-Sosa et al. (2006); Cho et al. (2006); Carland et al. (2010). For related structures, see: Swaminathan & Nigam (1967); Cao et al. (2007).

Experimental top

1,4-Bis(tosyloxy)anthraquinone was prepared by a stirred solution of 1,4-bis(hydroxyl)anthraquinone or quinizarin (0.241 g, 1.00 mmol) in 25 mL of dry dichloromethane was added triethylamine (0.205 g, 2.03 mmol) and p-toluenesulfonyl chloride (0.383 g, 2.01 mmol). The solution was stirred at room temperature for 24 hours. The precipitate was filtered off and then washed with water and dried over magnesium sulfate. Filtration of slurry gave a bright yellow-green solid. The final product was recrystallized in hexane:dichloromethane using slow evaporation which was suitable for X-ray diffraction analysis. Additionally, ¹H of 1,4-bis(tosyloxy)anthraquinone were recorded in CDCl₃ solution on a Varian Mercury Plus 400 spectrometer. ¹H NMR spectrum (δ, ppm): 7.94-8.02 (2H,m); 7.69-7.91 (6H,m); 7.45 (2H,s); 7.24-7.33 (4H,m); 2.35 (6H,s) (Zielske et al., 1987).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

9,10-Dioxoanthracene-1,4-diyl bis(4-methylbenzenesulfonate) top

Crystal data top

C₂₈H₂₀O₈S₂	Z = 2
M_r = 548.56	F(000) = 568
Triclinic, P1	D_x = 1.478 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6796 (2) Å	Cell parameters from 3943 reflections
b = 10.9426 (3) Å	θ = 2.6–27.1°
c = 13.1833 (4) Å	µ = 0.27 mm⁻¹
α = 111.122 (1)°	T = 296 K
β = 90.961 (1)°	Block, yellow–orange
γ = 107.190 (1)°	0.35 × 0.20 × 0.20 mm
V = 1232.41 (6) Å³

Data collection top

Bruker APEXII CCD diffractometer	5616 independent reflections
Radiation source: fine-focus sealed tube	3997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→12
T_min = 0.912, T_max = 0.948	k = −14→14
12983 measured reflections	l = −17→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0564P)² + 0.3809P] where P = (F_o² + 2F_c²)/3
5616 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.28 e Å⁻³
346 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₈H₂₀O₈S₂	γ = 107.190 (1)°
M_r = 548.56	V = 1232.41 (6) Å³
Triclinic, P1	Z = 2
a = 9.6796 (2) Å	Mo Kα radiation
b = 10.9426 (3) Å	µ = 0.27 mm⁻¹
c = 13.1833 (4) Å	T = 296 K
α = 111.122 (1)°	0.35 × 0.20 × 0.20 mm
β = 90.961 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5616 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3997 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.948	R_int = 0.031
12983 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	346 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.02	Δρ_max = 0.28 e Å⁻³
5616 reflections	Δρ_min = −0.30 e Å⁻³
343 parameters

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	0.0724 (2)	−0.3607 (2)	0.30321 (17)	0.0455 (5)
C2	0.2026 (2)	−0.2898 (2)	0.37289 (19)	0.0540 (5)
H2	0.2612	−0.3377	0.3859	0.065*
C3	0.2451 (2)	−0.1479 (2)	0.42300 (19)	0.0526 (5)
H3	0.3337	−0.0992	0.4688	0.063*
C4	0.1559 (2)	−0.07826 (19)	0.40504 (16)	0.0410 (4)
C4A	0.0214 (2)	−0.14744 (19)	0.33781 (15)	0.0381 (4)
C5	−0.3343 (2)	−0.0885 (3)	0.2748 (2)	0.0572 (6)
H5	−0.3097	0.0060	0.3157	0.069*
C5A	−0.2305 (2)	−0.1552 (2)	0.26945 (16)	0.0441 (4)
C6	−0.4726 (3)	−0.1623 (3)	0.2197 (2)	0.0700 (7)
H6	−0.5425	−0.1183	0.2251	0.084*
C7	−0.5085 (3)	−0.3014 (3)	0.1565 (2)	0.0713 (7)
H7	−0.6016	−0.3501	0.1173	0.086*
C8	−0.4074 (3)	−0.3691 (3)	0.1510 (2)	0.0616 (6)
H8	−0.4325	−0.4632	0.1084	0.074*
C8A	−0.2675 (2)	−0.2962 (2)	0.20916 (17)	0.0457 (5)
C9	−0.1623 (2)	−0.3716 (2)	0.20721 (17)	0.0465 (5)
C9A	−0.0210 (2)	−0.29290 (19)	0.28346 (16)	0.0404 (4)
C10	−0.0799 (2)	−0.0713 (2)	0.32586 (16)	0.0426 (4)
C11	−0.0130 (2)	−0.7359 (2)	0.09847 (17)	0.0465 (5)
C12	−0.0189 (3)	−0.8400 (2)	0.13582 (17)	0.0508 (5)
H12	0.0487	−0.8251	0.1935	0.061*
C13	−0.1266 (3)	−0.9662 (2)	0.08608 (19)	0.0571 (6)
H13	−0.1306	−1.0367	0.1107	0.068*
C14	−0.2286 (3)	−0.9906 (2)	0.00061 (19)	0.0575 (6)
C15	−0.2168 (3)	−0.8849 (3)	−0.0367 (2)	0.0693 (7)
H15	−0.2822	−0.9008	−0.0961	0.083*
C16	−0.1114 (3)	−0.7576 (2)	0.0115 (2)	0.0619 (6)
H16	−0.1063	−0.6875	−0.0139	0.074*
C17	−0.3479 (3)	−1.1281 (3)	−0.0518 (2)	0.0844 (9)
H17A	−0.3392	−1.1883	−0.0159	0.127*
H17B	−0.3392	−1.1692	−0.1282	0.127*
H17C	−0.4413	−1.1144	−0.0447	0.127*
C18	0.3179 (2)	0.32113 (19)	0.50215 (16)	0.0406 (4)
C19	0.4237 (2)	0.4068 (2)	0.59098 (17)	0.0491 (5)
H19	0.4989	0.3777	0.6082	0.059*
C20	0.4172 (3)	0.5357 (2)	0.65400 (19)	0.0552 (5)
H20	0.4894	0.5940	0.7133	0.066*
C21	0.3059 (2)	0.5800 (2)	0.6309 (2)	0.0533 (5)
C22	0.2026 (3)	0.4927 (2)	0.5408 (2)	0.0627 (6)
H22	0.1280	0.5223	0.5234	0.075*
C23	0.2062 (2)	0.3635 (2)	0.4759 (2)	0.0568 (6)
H23	0.1350	0.3061	0.4158	0.068*
C24	0.2962 (3)	0.7192 (2)	0.7032 (3)	0.0808 (9)
H24A	0.3768	0.7652	0.7615	0.121*
H24B	0.2062	0.7065	0.7337	0.121*
H24C	0.2995	0.7744	0.6603	0.121*
O1	−0.19121 (19)	−0.49172 (16)	0.14755 (15)	0.0704 (5)
O2	−0.04323 (17)	0.05362 (15)	0.36092 (15)	0.0641 (4)
O3	0.03027 (16)	−0.50532 (13)	0.25827 (12)	0.0530 (4)
O4	0.14116 (19)	−0.49740 (17)	0.09439 (14)	0.0711 (5)
O5	0.24035 (19)	−0.58494 (17)	0.21518 (16)	0.0765 (5)
O6	0.19989 (14)	0.06504 (13)	0.46365 (11)	0.0434 (3)
O7	0.2846 (2)	0.12386 (17)	0.30826 (13)	0.0737 (5)
O8	0.46239 (17)	0.14656 (16)	0.45212 (16)	0.0697 (5)
S1	0.32770 (6)	0.15885 (5)	0.42096 (4)	0.04743 (15)
S2	0.11835 (6)	−0.57384 (5)	0.16304 (5)	0.05089 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0499 (11)	0.0367 (10)	0.0512 (12)	0.0144 (9)	0.0099 (9)	0.0180 (9)
C2	0.0514 (12)	0.0494 (12)	0.0672 (14)	0.0226 (10)	0.0022 (11)	0.0240 (11)
C3	0.0479 (12)	0.0505 (12)	0.0569 (13)	0.0156 (10)	−0.0032 (10)	0.0186 (10)
C4	0.0441 (10)	0.0368 (10)	0.0396 (10)	0.0109 (8)	0.0060 (8)	0.0135 (8)
C4A	0.0397 (10)	0.0376 (10)	0.0388 (10)	0.0116 (8)	0.0063 (8)	0.0173 (8)
C5	0.0518 (13)	0.0649 (14)	0.0626 (14)	0.0238 (11)	0.0065 (10)	0.0291 (12)
C5A	0.0416 (10)	0.0503 (11)	0.0449 (11)	0.0135 (9)	0.0056 (8)	0.0244 (9)
C6	0.0480 (13)	0.0900 (19)	0.0858 (19)	0.0270 (13)	0.0071 (12)	0.0454 (16)
C7	0.0408 (13)	0.0908 (19)	0.0818 (18)	0.0077 (13)	−0.0053 (12)	0.0438 (16)
C8	0.0501 (13)	0.0571 (14)	0.0672 (15)	0.0024 (11)	−0.0046 (11)	0.0246 (12)
C8A	0.0405 (10)	0.0500 (11)	0.0461 (11)	0.0073 (9)	0.0040 (8)	0.0236 (9)
C9	0.0465 (11)	0.0404 (11)	0.0471 (11)	0.0076 (9)	0.0052 (9)	0.0158 (9)
C9A	0.0403 (10)	0.0390 (10)	0.0413 (10)	0.0106 (8)	0.0073 (8)	0.0164 (8)
C10	0.0428 (11)	0.0412 (11)	0.0455 (11)	0.0130 (9)	0.0052 (8)	0.0188 (9)
C11	0.0506 (11)	0.0455 (11)	0.0435 (11)	0.0206 (9)	0.0048 (9)	0.0130 (9)
C12	0.0610 (13)	0.0517 (12)	0.0408 (11)	0.0234 (10)	0.0063 (10)	0.0148 (9)
C13	0.0756 (16)	0.0475 (12)	0.0499 (13)	0.0205 (11)	0.0191 (11)	0.0198 (10)
C14	0.0603 (14)	0.0511 (13)	0.0481 (13)	0.0153 (11)	0.0129 (10)	0.0061 (10)
C15	0.0736 (17)	0.0646 (15)	0.0578 (15)	0.0224 (13)	−0.0144 (12)	0.0108 (12)
C16	0.0776 (17)	0.0521 (13)	0.0565 (14)	0.0241 (12)	−0.0045 (12)	0.0195 (11)
C17	0.0779 (19)	0.0662 (17)	0.0752 (19)	0.0004 (14)	0.0121 (15)	0.0069 (14)
C18	0.0389 (10)	0.0387 (10)	0.0435 (10)	0.0094 (8)	0.0053 (8)	0.0174 (8)
C19	0.0446 (11)	0.0488 (12)	0.0517 (12)	0.0149 (9)	−0.0005 (9)	0.0173 (10)
C20	0.0555 (13)	0.0462 (12)	0.0507 (13)	0.0090 (10)	−0.0001 (10)	0.0097 (10)
C21	0.0504 (12)	0.0403 (11)	0.0685 (15)	0.0115 (9)	0.0218 (11)	0.0218 (10)
C22	0.0486 (13)	0.0565 (14)	0.0903 (18)	0.0228 (11)	0.0054 (12)	0.0318 (13)
C23	0.0488 (12)	0.0510 (13)	0.0645 (14)	0.0116 (10)	−0.0071 (10)	0.0194 (11)
C24	0.0789 (19)	0.0469 (14)	0.111 (2)	0.0224 (13)	0.0374 (17)	0.0217 (14)
O1	0.0628 (11)	0.0473 (9)	0.0759 (12)	0.0118 (8)	−0.0066 (9)	0.0008 (8)
O2	0.0574 (10)	0.0394 (8)	0.0900 (12)	0.0142 (7)	−0.0070 (8)	0.0204 (8)
O3	0.0605 (9)	0.0348 (7)	0.0639 (9)	0.0163 (7)	0.0168 (7)	0.0181 (7)
O4	0.0729 (11)	0.0681 (11)	0.0697 (11)	0.0077 (9)	0.0174 (9)	0.0350 (9)
O5	0.0566 (10)	0.0625 (11)	0.0955 (14)	0.0258 (8)	−0.0134 (9)	0.0091 (9)
O6	0.0448 (8)	0.0353 (7)	0.0423 (7)	0.0068 (6)	0.0057 (6)	0.0108 (6)
O7	0.1037 (14)	0.0592 (10)	0.0436 (9)	0.0113 (9)	0.0181 (9)	0.0147 (7)
O8	0.0432 (9)	0.0529 (9)	0.1090 (14)	0.0186 (7)	0.0147 (9)	0.0240 (9)
S1	0.0476 (3)	0.0408 (3)	0.0491 (3)	0.0111 (2)	0.0124 (2)	0.0141 (2)
S2	0.0477 (3)	0.0467 (3)	0.0563 (3)	0.0174 (2)	0.0067 (2)	0.0158 (2)

Geometric parameters (Å, º) top

C1—C2	1.379 (3)	C13—C14	1.381 (3)
C1—O3	1.399 (2)	C13—H13	0.9300
C1—C9A	1.401 (3)	C14—C15	1.387 (4)
C2—C3	1.375 (3)	C14—C17	1.507 (3)
C2—H2	0.9300	C15—C16	1.373 (3)
C3—C4	1.376 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—H16	0.9300
C4—C4A	1.396 (3)	C17—H17A	0.9600
C4—O6	1.399 (2)	C17—H17B	0.9600
C4A—C9A	1.413 (3)	C17—H17C	0.9600
C4A—C10	1.500 (3)	C18—C19	1.379 (3)
C5—C6	1.370 (3)	C18—C23	1.380 (3)
C5—C5A	1.395 (3)	C18—S1	1.744 (2)
C5—H5	0.9300	C19—C20	1.376 (3)
C5A—C8A	1.385 (3)	C19—H19	0.9300
C5A—C10	1.484 (3)	C20—C21	1.375 (3)
C6—C7	1.376 (4)	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.378 (3)
C7—C8	1.380 (4)	C21—C24	1.510 (3)
C7—H7	0.9300	C22—C23	1.375 (3)
C8—C8A	1.394 (3)	C22—H22	0.9300
C8—H8	0.9300	C23—H23	0.9300
C8A—C9	1.484 (3)	C24—H24A	0.9600
C9—O1	1.206 (2)	C24—H24B	0.9600
C9—C9A	1.502 (3)	C24—H24C	0.9600
C10—O2	1.209 (2)	O3—S2	1.6126 (15)
C11—C12	1.383 (3)	O4—S2	1.4180 (17)
C11—C16	1.383 (3)	O5—S2	1.4140 (18)
C11—S2	1.740 (2)	O6—S1	1.6094 (14)
C12—C13	1.377 (3)	O7—S1	1.4153 (18)
C12—H12	0.9300	O8—S1	1.4185 (17)

C2—C1—O3	117.61 (18)	C13—C14—C17	121.2 (2)
C2—C1—C9A	122.05 (18)	C15—C14—C17	120.9 (2)
O3—C1—C9A	120.18 (18)	C16—C15—C14	122.0 (2)
C3—C2—C1	119.6 (2)	C16—C15—H15	119.0
C3—C2—H2	120.2	C14—C15—H15	119.0
C1—C2—H2	120.2	C15—C16—C11	118.5 (2)
C2—C3—C4	119.7 (2)	C15—C16—H16	120.7
C2—C3—H3	120.1	C11—C16—H16	120.7
C4—C3—H3	120.1	C14—C17—H17A	109.5
C3—C4—C4A	122.00 (18)	C14—C17—H17B	109.5
C3—C4—O6	117.29 (17)	H17A—C17—H17B	109.5
C4A—C4—O6	120.54 (17)	C14—C17—H17C	109.5
C4—C4A—C9A	118.59 (17)	H17A—C17—H17C	109.5
C4—C4A—C10	121.41 (17)	H17B—C17—H17C	109.5
C9A—C4A—C10	119.96 (17)	C19—C18—C23	120.68 (19)
C6—C5—C5A	119.9 (2)	C19—C18—S1	119.46 (16)
C6—C5—H5	120.0	C23—C18—S1	119.85 (16)
C5A—C5—H5	120.0	C20—C19—C18	119.4 (2)
C8A—C5A—C5	120.04 (19)	C20—C19—H19	120.3
C8A—C5A—C10	121.30 (18)	C18—C19—H19	120.3
C5—C5A—C10	118.63 (19)	C21—C20—C19	121.2 (2)
C5—C6—C7	120.3 (2)	C21—C20—H20	119.4
C5—C6—H6	119.8	C19—C20—H20	119.4
C7—C6—H6	119.8	C20—C21—C22	118.0 (2)
C6—C7—C8	120.4 (2)	C20—C21—C24	120.9 (2)
C6—C7—H7	119.8	C22—C21—C24	121.1 (2)
C8—C7—H7	119.8	C23—C22—C21	122.2 (2)
C7—C8—C8A	119.9 (2)	C23—C22—H22	118.9
C7—C8—H8	120.0	C21—C22—H22	118.9
C8A—C8—H8	120.0	C22—C23—C18	118.4 (2)
C5A—C8A—C8	119.3 (2)	C22—C23—H23	120.8
C5A—C8A—C9	121.30 (18)	C18—C23—H23	120.8
C8—C8A—C9	119.3 (2)	C21—C24—H24A	109.5
O1—C9—C8A	120.74 (19)	C21—C24—H24B	109.5
O1—C9—C9A	122.00 (19)	H24A—C24—H24B	109.5
C8A—C9—C9A	117.25 (17)	C21—C24—H24C	109.5
C1—C9A—C4A	117.97 (17)	H24A—C24—H24C	109.5
C1—C9A—C9	121.38 (17)	H24B—C24—H24C	109.5
C4A—C9A—C9	120.65 (17)	C1—O3—S2	116.74 (12)
O2—C10—C5A	119.98 (18)	C4—O6—S1	116.91 (11)
O2—C10—C4A	122.49 (18)	O7—S1—O8	118.31 (12)
C5A—C10—C4A	117.53 (17)	O7—S1—O6	107.69 (9)
C12—C11—C16	121.1 (2)	O8—S1—O6	108.43 (9)
C12—C11—S2	119.64 (17)	O7—S1—C18	111.86 (11)
C16—C11—S2	119.27 (17)	O8—S1—C18	109.96 (10)
C13—C12—C11	118.8 (2)	O6—S1—C18	98.69 (8)
C13—C12—H12	120.6	O5—S2—O4	119.21 (12)
C11—C12—H12	120.6	O5—S2—O3	107.16 (10)
C12—C13—C14	121.7 (2)	O4—S2—O3	107.48 (10)
C12—C13—H13	119.2	O5—S2—C11	110.58 (10)
C14—C13—H13	119.2	O4—S2—C11	111.42 (11)
C13—C14—C15	117.8 (2)	O3—S2—C11	98.85 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O4ⁱ	0.93	2.48	3.333 (3)	153
C3—H3···O8ⁱⁱ	0.93	2.49	3.245 (3)	139

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₀O₈S₂
M_r	548.56
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.6796 (2), 10.9426 (3), 13.1833 (4)
α, β, γ (°)	111.122 (1), 90.961 (1), 107.190 (1)
V (Å³)	1232.41 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.35 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.912, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	12983, 5616, 3997
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.127, 1.02
No. of reflections	5616
No. of parameters	343
No. of restraints	346
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.30

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O4ⁱ	0.93	2.48	3.333 (3)	153.0
C3—H3···O8ⁱⁱ	0.93	2.49	3.245 (3)	139.0

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

Acknowledgements

We thank the Organizing Commitee for a bursary to attend the XXII IUCr 2011 Congress, the American Crystallographic Association (ACA) for a scholarship to attend the 2009 ACA Summer Course in Small Molecule Crystallography, the 90th Anniversary of Chulalongkorn University Fund (Ratchadaphisek Somphot Endowment Fund), the Thai Government Stimulus Package 2 (TKK2555) project, the Center for Petroleum Petrochemicals and Advanced Materials, and the Research Centre for Bioorganic Chemistry (RCBC), Chulalongkorn University, for financial support.

References

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Volume 68| Part 5| May 2012| Pages o1423-o1424

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