N,N′-Diphenyl-9,10-dioxo-9,10-di­hydro­anthracene-2,7-disulfonamide

Yuan, W.-G.; Zhang, H.-L.

doi:10.1107/S1600536813017303

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1172

https://doi.org/10.1107/S1600536813017303

Open

access

N,N′-Diphenyl-9,10-dioxo-9,10-dihydroanthracene-2,7-disulfonamide

Wei-Guan Yuan ^a ^* and Hong-Ling Zhang ^a

^aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, School of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: yuanweiguan_1@cwnu.edu.cn

(Received 7 June 2013; accepted 23 June 2013; online 29 June 2013)

The title molecule, C₂₆H₁₈N₂O₆S₂, has an overall Z-shaped conformation, in which the benzene rings are inclined to the anthraquinone mean plane by 60.60 (9) and 50.66 (13)°. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link the molecules 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_r = 518.54
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.059
wR(F²) = 0.146
S = 1.00
4512 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) -x+1, -y+2, -z+2; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+3, -z+2.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813017303/cv5417sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813017303/cv5417Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813017303/cv5417Isup3.cml

checkCIF report

Comment top

In recent years, sulfonamide and its derivatives attract more attention due to their applications in molecular recognition (Kuljit et al., 2011). They can be used as fluorescent sensors to detect heavy metal ions (Chen et al., 2000) in view of good sensitivity, high selectivity, fast response and convenient observation (Valeur & Leray, 2000). Normally, a fluorescent sensor consists of a receptor for recognition and a fluorophore for signaling the recognition event. Anthraquinone and many of its derivatives are analogous to naphthalene dyes, therefore, they have been extensively explored as fluorescence probes in various chemical and biological systems (Lu et al., 2006; Liu et al., 2011). Herein, we report the synthesis and crystal structure of the title compound, (I), in which the anthraquinone fragment acts as a fluorophore.

In (I) (Fig. 1), the bond lengths and angles are normal (Allen et al., 1987) and correspond well to those observed in the related compound (Li et al., 2009). Two benzene rings are inclined to the anthraquinone mean plane at 60.60 (9)° and 50.66 (13)°, respectively. In the crystal, intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to bc plane.

Related literature top

For applications of sulfonamide derivitives, see: Valeur & Leray (2000); Chen et al. (2000); Kuljit et al. (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 top

A mixture of aniline (372 mg, 4 mmol) and triethylamine(8 mmol) in dry dichloroethane(20 ml) was stirred at RT, then, the solution of N,N^'– bisphenyl- 9,10- dioxo-9,10-dihydro-2,7- anthracenedisulfonyl chloride (977 mg, 2.2 mmol) in dry dichloroethane (30 ml) was added during 5 min, the mixture was stirred at RT for 8 h under nitrogen in air. Then the solvent was removed completely under vacuum and the solid washed with water yielding the title compound (Kuljit et al.,2011; Zeng et al.,2002). Yellow needlelike single crystals suitable for X-ray diffraction were obtained by volatilizing dichloromethane slowly.

Structure description top

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

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

N,N'-Diphenyl-9,10-dioxo-9,10-dihydroanthracene-2,7-disulfonamide top

Crystal data top

C₂₆H₁₈N₂O₆S₂	F(000) = 1072
M_r = 518.54	D_x = 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

Data collection top

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

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.040P)²] where P = (F_o² + 2F_c²)/3
4512 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₆H₁₈N₂O₆S₂	V = 2300.6 (14) Å³
M_r = 518.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.247 (4) Å	µ = 0.28 mm⁻¹
b = 6.395 (2) Å	T = 293 K
c = 36.265 (12) Å	0.26 × 0.17 × 0.14 mm
β = 104.511 (12)°

Data collection top

Bruker APEXII CCD diffractometer	4512 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1965 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.962	R_int = 0.088
12233 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.00	Δρ_max = 0.33 e Å⁻³
4512 reflections	Δρ_min = −0.32 e Å⁻³
325 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, −y+3, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈N₂O₆S₂
M_r	518.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.247 (4), 6.395 (2), 36.265 (12)
β (°)	104.511 (12)
V (Å³)	2300.6 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.26 × 0.17 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.931, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	12233, 4512, 1965
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.146, 1.00
No. of reflections	4512
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.32

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, −y+3, −z+2.

Acknowledgements

The authors thank the Scientific Researching Fund Projects of China West Normal University (grant No. 06B003).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, L. P., Yang, L. T., Li, H. W., Gao, Y., Deng, D. Y., Wu, Y. Q. & Ma, L. J. (2000). Inorg. Chem. 50, 10028—0032. Google Scholar
Kuljit, K. & Subodh, K. (2011). Dalton Trans. 40, 2451–2458. Web of Science PubMed Google Scholar
Li, H. W., Li, Y., Dang, Y. Q., Ma, L. J., Wu, Y. Q. & Hou, G. F. (2009). Chem. Commun. 29, 4453–4455. Web of Science CSD CrossRef Google Scholar
Liu, Y. L., Sun, Y., Du, J., Lv, X., Zhao, Y., Chen, M. L., Wang, P. & Guo, W. (2011). Org. Biomol. Chem. 9, 432–437. Web of Science CrossRef CAS PubMed Google Scholar
Lu, Z. K., Lord, S. J., Wang, H., Moerner, W. E. & Twieg, R. J. (2006). J. Org. Chem. 71, 9651–9657. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Valeur, B. & Leray, I. (2000). Coord Chem. Rev. 205, 3–40. Web of Science CrossRef CAS Google Scholar
Zeng, B. B. & King, S. B. (2002). Synthesis, 16, 2335–2337. Google Scholar