9,10-Dioxoanthracene-1,4-diyl bis-(4-methyl-benzene-sulfonate).

The title mol-ecule, C(28)H(20)O(8)S(2), 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 mol-ecules 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 = 548.56

Triclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.02

5616 reflections

343 parameters

346 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015814/cv5268sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812015814/cv5268Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H20O8S2	Z = 2
Mr = 548.56	F(000) = 568
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0564P)2 + 0.3809P] where P = (Fo2 + 2Fc2)/3
5616 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.28 e Å−3
346 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .