N,N'-Diphenyl-9,10-dioxo-9,10-di-hydro-anthracene-2,7-disulfonamide.

The title mol-ecule, C26H18N2O6S2, has an overall Z-shaped conformation, in which the benzene rings are inclined to the anthra-quinone mean plane by 60.60 (9) and 50.66 (13)°. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the bc plane.

Related literature

For applications of sulfonamide derivitives, see: Valeur & Leray (2000 ▶); Chen et al. (2000 ▶); Kuljit & Subodh (2011 ▶). For applications of anthra­quinone derivitives, see: Lu et al. (2006 ▶); Liu et al. (2011 ▶). For details of the synthesis, see: Kuljit & Subodh (2011 ▶); Zeng & King (2002 ▶). For a related structure, see: Li et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C26H18N2O6S2

M = 518.54

Monoclinic,

a = 10.247 (4) Å

b = 6.395 (2) Å

c = 36.265 (12) Å

β = 104.511 (12)°

V = 2300.6 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.26 × 0.17 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.931, T max = 0.962

12233 measured reflections

4512 independent reflections

1965 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.146

S = 1.00

4512 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.32 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813017303/cv5417sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017303/cv5417Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017303/cv5417Isup3.cml

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

C26H18N2O6S2	F(000) = 1072
Mr = 518.54	Dx = 1.497 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 620 reflections
a = 10.247 (4) Å	θ = 2.7–17.7°
b = 6.395 (2) Å	µ = 0.28 mm−1
c = 36.265 (12) Å	T = 293 K
β = 104.511 (12)°	Needle, yellow
V = 2300.6 (14) Å3	0.26 × 0.17 × 0.14 mm
Z = 4

Bruker APEXII CCD diffractometer	4512 independent reflections
Radiation source: fine-focus sealed tube	1965 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
φ and ω scans	θmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→12
Tmin = 0.931, Tmax = 0.962	k = −7→7
12233 measured reflections	l = −44→44

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3
4512 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.32 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
S1	0.58554 (13)	0.18230 (18)	0.79332 (3)	0.0572 (4)
S2	0.28393 (12)	1.46829 (17)	0.92991 (3)	0.0563 (4)
O1	0.6506 (3)	−0.0105 (4)	0.80672 (8)	0.0677 (9)
O2	0.4492 (3)	0.1852 (4)	0.77093 (8)	0.0677 (9)
O3	0.3522 (3)	0.8677 (5)	0.83377 (8)	0.0714 (10)
O4	0.7155 (3)	0.6645 (5)	0.96336 (7)	0.0645 (9)
O5	0.2258 (3)	1.5295 (4)	0.89183 (7)	0.0634 (9)
O6	0.3526 (3)	1.6176 (4)	0.95722 (8)	0.0720 (9)
N1	0.6729 (4)	0.3019 (5)	0.76842 (9)	0.0580 (10)
H1B	0.6322	0.3522	0.7466	0.070*
N2	0.1695 (3)	1.3670 (5)	0.94892 (9)	0.0566 (10)
H2B	0.1538	1.4248	0.9688	0.068*
C1	0.8998 (6)	0.1581 (8)	0.77943 (12)	0.0693 (14)
H1A	0.8636	0.0292	0.7703	0.083*
C2	1.0385 (7)	0.1863 (11)	0.79121 (14)	0.0858 (17)
H2A	1.0954	0.0752	0.7896	0.103*
C3	1.0928 (6)	0.3734 (12)	0.80505 (14)	0.0867 (18)
H3A	1.1858	0.3900	0.8129	0.104*
C4	1.0079 (7)	0.5385 (10)	0.80733 (13)	0.0823 (16)
H4A	1.0444	0.6671	0.8165	0.099*
C5	0.8700 (6)	0.5145 (8)	0.79609 (12)	0.0665 (13)
H5A	0.8138	0.6253	0.7984	0.080*
C6	0.8160 (5)	0.3270 (8)	0.78157 (11)	0.0556 (12)
C7	0.6861 (4)	0.2840 (7)	0.86814 (11)	0.0547 (12)
H7A	0.7385	0.1643	0.8693	0.066*
C8	0.5946 (4)	0.3395 (7)	0.83429 (11)	0.0472 (11)
C9	0.5143 (4)	0.5151 (6)	0.83231 (11)	0.0481 (11)
H9A	0.4528	0.5501	0.8096	0.058*
C10	0.5262 (4)	0.6392 (6)	0.86460 (11)	0.0455 (11)
C11	0.6200 (4)	0.5845 (6)	0.89853 (11)	0.0452 (11)
C12	0.6987 (4)	0.4077 (7)	0.90007 (12)	0.0512 (11)
H12A	0.7603	0.3719	0.9227	0.061*
C13	0.6374 (4)	0.7168 (7)	0.93335 (12)	0.0489 (11)
C14	0.5571 (4)	0.9119 (6)	0.93028 (11)	0.0455 (11)
C15	0.4591 (4)	0.9599 (6)	0.89736 (11)	0.0438 (10)
C16	0.4378 (4)	0.8243 (7)	0.86281 (11)	0.0502 (11)
C17	0.3778 (4)	1.1325 (7)	0.89652 (11)	0.0503 (11)
H17A	0.3115	1.1640	0.8746	0.060*
C18	0.3949 (4)	1.2593 (6)	0.92850 (11)	0.0478 (11)
C19	0.4951 (4)	1.2139 (7)	0.96133 (11)	0.0551 (12)
H19A	0.5071	1.2998	0.9826	0.066*
C20	0.5760 (4)	1.0420 (7)	0.96214 (11)	0.0538 (12)
H20A	0.6434	1.0121	0.9839	0.065*
C21	0.0947 (4)	1.1849 (7)	0.93340 (12)	0.0488 (11)
C22	0.0754 (5)	1.0319 (8)	0.95845 (12)	0.0642 (13)
H22A	0.1091	1.0515	0.9845	0.077*
C23	0.0068 (5)	0.8506 (8)	0.94520 (17)	0.0824 (16)
H23A	−0.0066	0.7488	0.9622	0.099*
C24	−0.0416 (5)	0.8218 (8)	0.90673 (17)	0.0739 (15)
H24A	−0.0871	0.6993	0.8975	0.089*
C25	−0.0229 (5)	0.9733 (8)	0.88214 (14)	0.0710 (14)
H25A	−0.0551	0.9522	0.8561	0.085*
C26	0.0431 (4)	1.1582 (8)	0.89523 (12)	0.0626 (13)
H26A	0.0521	1.2626	0.8782	0.075*

	U11	U22	U33	U12	U13	U23
S1	0.0700 (9)	0.0481 (7)	0.0503 (7)	−0.0020 (7)	0.0094 (6)	−0.0015 (6)
S2	0.0659 (8)	0.0510 (7)	0.0529 (8)	−0.0088 (7)	0.0166 (6)	−0.0050 (6)
O1	0.095 (2)	0.0398 (18)	0.0637 (19)	0.0054 (17)	0.0110 (18)	0.0079 (15)
O2	0.065 (2)	0.061 (2)	0.0660 (19)	−0.0071 (17)	−0.0047 (17)	−0.0067 (16)
O3	0.083 (2)	0.079 (2)	0.0415 (18)	0.0234 (19)	−0.0047 (17)	−0.0046 (16)
O4	0.066 (2)	0.078 (2)	0.0431 (18)	0.0071 (18)	0.0017 (16)	0.0034 (16)
O5	0.081 (2)	0.0580 (19)	0.0484 (18)	0.0018 (17)	0.0117 (17)	0.0043 (15)
O6	0.086 (2)	0.057 (2)	0.066 (2)	−0.0179 (18)	0.0065 (18)	−0.0195 (16)
N1	0.076 (3)	0.061 (2)	0.0359 (19)	0.001 (2)	0.013 (2)	0.0038 (18)
N2	0.063 (2)	0.062 (2)	0.051 (2)	−0.006 (2)	0.027 (2)	−0.0133 (18)
C1	0.087 (4)	0.074 (4)	0.048 (3)	0.012 (3)	0.021 (3)	−0.002 (3)
C2	0.088 (5)	0.118 (5)	0.059 (3)	0.035 (4)	0.032 (3)	0.017 (4)
C3	0.071 (4)	0.138 (6)	0.050 (3)	−0.007 (4)	0.014 (3)	0.018 (4)
C4	0.093 (5)	0.099 (5)	0.053 (3)	−0.012 (4)	0.015 (3)	0.006 (3)
C5	0.083 (4)	0.065 (4)	0.054 (3)	0.007 (3)	0.022 (3)	0.001 (3)
C6	0.079 (4)	0.054 (3)	0.035 (2)	0.007 (3)	0.018 (2)	0.001 (2)
C7	0.057 (3)	0.056 (3)	0.051 (3)	−0.001 (2)	0.012 (2)	0.002 (2)
C8	0.048 (3)	0.051 (3)	0.045 (3)	−0.006 (2)	0.015 (2)	−0.001 (2)
C9	0.047 (3)	0.052 (3)	0.041 (2)	−0.004 (2)	0.003 (2)	0.005 (2)
C10	0.051 (3)	0.049 (3)	0.036 (2)	−0.006 (2)	0.011 (2)	0.004 (2)
C11	0.045 (3)	0.049 (3)	0.041 (3)	−0.009 (2)	0.011 (2)	0.006 (2)
C12	0.048 (3)	0.060 (3)	0.044 (3)	−0.006 (2)	0.008 (2)	0.007 (2)
C13	0.045 (3)	0.057 (3)	0.041 (3)	−0.009 (2)	0.004 (2)	0.008 (2)
C14	0.046 (3)	0.051 (3)	0.037 (2)	−0.011 (2)	0.007 (2)	0.004 (2)
C15	0.052 (3)	0.044 (3)	0.036 (2)	−0.009 (2)	0.013 (2)	0.004 (2)
C16	0.055 (3)	0.056 (3)	0.038 (2)	−0.001 (2)	0.009 (2)	0.005 (2)
C17	0.054 (3)	0.056 (3)	0.040 (3)	−0.010 (2)	0.008 (2)	0.005 (2)
C18	0.050 (3)	0.050 (3)	0.044 (3)	−0.011 (2)	0.010 (2)	0.000 (2)
C19	0.066 (3)	0.058 (3)	0.041 (3)	−0.013 (3)	0.012 (2)	−0.009 (2)
C20	0.053 (3)	0.064 (3)	0.039 (3)	−0.007 (3)	0.001 (2)	0.000 (2)
C21	0.045 (3)	0.051 (3)	0.051 (3)	−0.001 (2)	0.013 (2)	−0.002 (2)
C22	0.064 (3)	0.077 (4)	0.051 (3)	−0.002 (3)	0.012 (3)	0.000 (3)
C23	0.085 (4)	0.072 (4)	0.095 (4)	−0.011 (3)	0.032 (4)	0.017 (3)
C24	0.065 (4)	0.060 (3)	0.100 (4)	−0.012 (3)	0.028 (3)	−0.005 (3)
C25	0.063 (3)	0.078 (4)	0.073 (3)	−0.010 (3)	0.019 (3)	−0.014 (3)
C26	0.064 (3)	0.070 (3)	0.052 (3)	−0.008 (3)	0.010 (3)	−0.002 (3)

S1—O1	1.428 (3)	C9—C10	1.394 (5)
S1—O2	1.430 (3)	C9—H9A	0.9300
S1—N1	1.615 (4)	C10—C11	1.402 (5)
S1—C8	1.777 (4)	C10—C16	1.482 (6)
S2—O5	1.415 (3)	C11—C12	1.382 (5)
S2—O6	1.428 (3)	C11—C13	1.493 (5)
S2—N2	1.636 (3)	C12—H12A	0.9300
S2—C18	1.764 (4)	C13—C14	1.483 (5)
O3—C16	1.222 (4)	C14—C15	1.388 (5)
O4—C13	1.225 (4)	C14—C20	1.398 (5)
N1—C6	1.433 (5)	C15—C17	1.379 (5)
N1—H1B	0.8600	C15—C16	1.494 (5)
N2—C21	1.429 (5)	C17—C18	1.390 (5)
N2—H2B	0.8600	C17—H17A	0.9300
C1—C2	1.390 (7)	C18—C19	1.394 (5)
C1—C6	1.394 (6)	C19—C20	1.372 (5)
C1—H1A	0.9300	C19—H19A	0.9300
C2—C3	1.361 (7)	C20—H20A	0.9300
C2—H2A	0.9300	C21—C26	1.363 (5)
C3—C4	1.383 (7)	C21—C22	1.383 (6)
C3—H3A	0.9300	C22—C23	1.379 (6)
C4—C5	1.378 (6)	C22—H22A	0.9300
C4—H4A	0.9300	C23—C24	1.371 (6)
C5—C6	1.370 (6)	C23—H23A	0.9300
C5—H5A	0.9300	C24—C25	1.362 (6)
C7—C12	1.382 (5)	C24—H24A	0.9300
C7—C8	1.391 (5)	C25—C26	1.386 (6)
C7—H7A	0.9300	C25—H25A	0.9300
C8—C9	1.384 (5)	C26—H26A	0.9300
O1—S1—O2	120.75 (19)	C12—C11—C10	120.3 (4)
O1—S1—N1	108.8 (2)	C12—C11—C13	119.0 (4)
O2—S1—N1	106.02 (19)	C10—C11—C13	120.7 (4)
O1—S1—C8	106.36 (19)	C11—C12—C7	120.3 (4)
O2—S1—C8	107.9 (2)	C11—C12—H12A	119.9
N1—S1—C8	106.22 (19)	C7—C12—H12A	119.9
O5—S2—O6	120.37 (19)	O4—C13—C14	121.6 (4)
O5—S2—N2	110.50 (18)	O4—C13—C11	120.6 (4)
O6—S2—N2	104.67 (19)	C14—C13—C11	117.8 (4)
O5—S2—C18	107.33 (19)	C15—C14—C20	120.0 (4)
O6—S2—C18	108.5 (2)	C15—C14—C13	121.3 (4)
N2—S2—C18	104.34 (18)	C20—C14—C13	118.7 (4)
C6—N1—S1	122.1 (3)	C17—C15—C14	120.0 (4)
C6—N1—H1B	119.0	C17—C15—C16	119.0 (4)
S1—N1—H1B	119.0	C14—C15—C16	121.0 (4)
C21—N2—S2	121.8 (3)	O3—C16—C10	121.2 (4)
C21—N2—H2B	119.1	O3—C16—C15	120.9 (4)
S2—N2—H2B	119.1	C10—C16—C15	117.9 (4)
C2—C1—C6	118.6 (5)	C15—C17—C18	120.0 (4)
C2—C1—H1A	120.7	C15—C17—H17A	120.0
C6—C1—H1A	120.7	C18—C17—H17A	120.0
C3—C2—C1	121.3 (6)	C17—C18—C19	120.2 (4)
C3—C2—H2A	119.3	C17—C18—S2	121.2 (3)
C1—C2—H2A	119.3	C19—C18—S2	118.4 (3)
C2—C3—C4	119.2 (6)	C20—C19—C18	119.8 (4)
C2—C3—H3A	120.4	C20—C19—H19A	120.1
C4—C3—H3A	120.4	C18—C19—H19A	120.1
C5—C4—C3	120.7 (6)	C19—C20—C14	120.1 (4)
C5—C4—H4A	119.6	C19—C20—H20A	120.0
C3—C4—H4A	119.6	C14—C20—H20A	120.0
C6—C5—C4	119.8 (5)	C26—C21—C22	119.7 (4)
C6—C5—H5A	120.1	C26—C21—N2	122.4 (4)
C4—C5—H5A	120.1	C22—C21—N2	117.9 (4)
C5—C6—C1	120.3 (5)	C23—C22—C21	120.7 (4)
C5—C6—N1	120.5 (5)	C23—C22—H22A	119.7
C1—C6—N1	119.2 (5)	C21—C22—H22A	119.7
C12—C7—C8	119.6 (4)	C24—C23—C22	119.4 (5)
C12—C7—H7A	120.2	C24—C23—H23A	120.3
C8—C7—H7A	120.2	C22—C23—H23A	120.3
C9—C8—C7	120.9 (4)	C25—C24—C23	119.8 (5)
C9—C8—S1	120.7 (3)	C25—C24—H24A	120.1
C7—C8—S1	118.4 (3)	C23—C24—H24A	120.1
C8—C9—C10	119.5 (4)	C24—C25—C26	121.3 (5)
C8—C9—H9A	120.3	C24—C25—H25A	119.4
C10—C9—H9A	120.3	C26—C25—H25A	119.4
C9—C10—C11	119.5 (4)	C21—C26—C25	119.1 (5)
C9—C10—C16	119.6 (4)	C21—C26—H26A	120.4
C11—C10—C16	121.0 (4)	C25—C26—H26A	120.4
O1—S1—N1—C6	−47.7 (4)	C11—C13—C14—C15	6.4 (6)
O2—S1—N1—C6	−179.0 (3)	O4—C13—C14—C20	2.6 (6)
C8—S1—N1—C6	66.5 (4)	C11—C13—C14—C20	−177.5 (4)
O5—S2—N2—C21	60.2 (3)	C20—C14—C15—C17	−1.9 (6)
O6—S2—N2—C21	−168.9 (3)	C13—C14—C15—C17	174.1 (4)
C18—S2—N2—C21	−54.9 (3)	C20—C14—C15—C16	179.5 (4)
C6—C1—C2—C3	0.8 (7)	C13—C14—C15—C16	−4.5 (6)
C1—C2—C3—C4	−0.1 (8)	C9—C10—C16—O3	1.8 (6)
C2—C3—C4—C5	0.6 (8)	C11—C10—C16—O3	−177.0 (4)
C3—C4—C5—C6	−1.7 (7)	C9—C10—C16—C15	−176.6 (4)
C4—C5—C6—C1	2.4 (7)	C11—C10—C16—C15	4.7 (6)
C4—C5—C6—N1	−177.6 (4)	C17—C15—C16—O3	2.0 (6)
C2—C1—C6—C5	−1.9 (7)	C14—C15—C16—O3	−179.4 (4)
C2—C1—C6—N1	178.1 (4)	C17—C15—C16—C10	−179.7 (4)
S1—N1—C6—C5	−102.5 (4)	C14—C15—C16—C10	−1.1 (6)
S1—N1—C6—C1	77.5 (5)	C14—C15—C17—C18	0.6 (6)
C12—C7—C8—C9	−1.1 (6)	C16—C15—C17—C18	179.3 (4)
C12—C7—C8—S1	177.7 (3)	C15—C17—C18—C19	0.7 (6)
O1—S1—C8—C9	−164.6 (3)	C15—C17—C18—S2	−174.6 (3)
O2—S1—C8—C9	−33.8 (4)	O5—S2—C18—C17	−24.7 (4)
N1—S1—C8—C9	79.5 (4)	O6—S2—C18—C17	−156.2 (3)
O1—S1—C8—C7	16.5 (4)	N2—S2—C18—C17	92.6 (4)
O2—S1—C8—C7	147.4 (3)	O5—S2—C18—C19	160.0 (3)
N1—S1—C8—C7	−99.3 (3)	O6—S2—C18—C19	28.4 (4)
C7—C8—C9—C10	0.7 (6)	N2—S2—C18—C19	−82.7 (3)
S1—C8—C9—C10	−178.1 (3)	C17—C18—C19—C20	−0.7 (6)
C8—C9—C10—C11	0.3 (6)	S2—C18—C19—C20	174.7 (3)
C8—C9—C10—C16	−178.4 (4)	C18—C19—C20—C14	−0.6 (6)
C9—C10—C11—C12	−0.8 (6)	C15—C14—C20—C19	1.9 (6)
C16—C10—C11—C12	177.9 (4)	C13—C14—C20—C19	−174.2 (4)
C9—C10—C11—C13	178.6 (4)	S2—N2—C21—C26	−43.2 (5)
C16—C10—C11—C13	−2.7 (6)	S2—N2—C21—C22	136.7 (3)
C10—C11—C12—C7	0.3 (6)	C26—C21—C22—C23	1.3 (7)
C13—C11—C12—C7	−179.1 (4)	N2—C21—C22—C23	−178.6 (4)
C8—C7—C12—C11	0.6 (6)	C21—C22—C23—C24	0.6 (7)
C12—C11—C13—O4	−3.5 (6)	C22—C23—C24—C25	−0.8 (8)
C10—C11—C13—O4	177.2 (4)	C23—C24—C25—C26	−0.7 (8)
C12—C11—C13—C14	176.6 (4)	C22—C21—C26—C25	−2.8 (7)
C10—C11—C13—C14	−2.8 (6)	N2—C21—C26—C25	177.0 (4)
O4—C13—C14—C15	−173.5 (4)	C24—C25—C26—C21	2.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O4i	0.86	2.55	3.110 (4)	123
N1—H1B···O2ii	0.86	2.32	2.952 (5)	131
C19—H19A···O6iii	0.93	2.35	3.164 (5)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O4i	0.86	2.55	3.110 (4)	123
N1—H1B⋯O2ii	0.86	2.32	2.952 (5)	131
C19—H19A⋯O6iii	0.93	2.35	3.164 (5)	146

Symmetry codes: (i) ; (ii) ; (iii) .