5,11-Ditosyl-5H,11H-dibenzo[b,f][1,5]diazo-cine-6,12-dione acetic acid hemisolvate.

The mol-ecular structure of the title compound, C28H22N2O6S2·0.5CH3COOH, is built up from three fused rings, two six and one eight membered. The eight-membered ring shows a boat conformation and the dihedral angle between the two benzene groups attached thereto is 66.43 (11)°, resulting in a V-shaped geometry. Two tosyl substituents are bound to the N atoms. The planes through the tolyl rings are roughly perpendicular, as indicated by the dihedral angle of 82.44 (12)°. In the crystal, the mol-ecule and its inversion-related symmetry-equivalent are linked to the acetic acid solvent mol-ecule by non-classical O-H⋯O and C-H⋯O hydrogen bonds. Two half-occupied acetic acid solvent mol-ecules are disordered at the same site and linked by a center of symmetry.

Related literature

For the pharmacological activity of sulfonamides, see: Brzozowski et al. (2010 ▶); Drew (2000 ▶); Garaj et al. (2005 ▶). For their anti­proliferative activity, see: Abbassi et al. (2012 ▶); Bouissane et al. (2006 ▶); Lopez et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C28H22N2O6S2·0.5C2H4O2

M = 576.62

Triclinic,

a = 8.6933 (11) Å

b = 11.1746 (18) Å

c = 14.8051 (19) Å

α = 87.042 (4)°

β = 74.370 (5)°

γ = 75.097 (4)°

V = 1338.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.41 × 0.35 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer

19664 measured reflections

5446 independent reflections

4262 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.02

5446 reflections

370 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536813007903/im2423sup1.cif

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

C28H22N2O6S2·0.5C2H4O2	Z = 2
Mr = 576.62	F(000) = 600
Triclinic, P1	Dx = 1.431 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6933 (11) Å	Cell parameters from 5446 reflections
b = 11.1746 (18) Å	θ = 2.4–26.4°
c = 14.8051 (19) Å	µ = 0.25 mm−1
α = 87.042 (4)°	T = 296 K
β = 74.370 (5)°	Prismatic, colourless
γ = 75.097 (4)°	0.41 × 0.35 × 0.27 mm
V = 1338.2 (3) Å3

Bruker X8 APEX diffractometer	4262 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 26.4°, θmin = 2.4°
φ and ω scans	h = −10→8
19664 measured reflections	k = −13→13
5447 independent reflections	l = −18→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.7987P] where P = (Fo2 + 2Fc2)/3
5446 reflections	(Δ/σ)max = 0.001
370 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.47 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	Occ. (<1)
C1	0.1314 (2)	0.04736 (19)	0.66644 (14)	0.0182 (4)
C2	0.1389 (3)	−0.0156 (2)	0.58638 (15)	0.0243 (5)
H2	0.1228	0.0280	0.5331	0.029*
C3	0.1703 (3)	−0.1427 (2)	0.58609 (16)	0.0325 (5)
H3	0.1734	−0.1850	0.5329	0.039*
C4	0.1973 (3)	−0.2080 (2)	0.66490 (16)	0.0352 (6)
H4	0.2197	−0.2940	0.6642	0.042*
C5	0.1909 (3)	−0.1454 (2)	0.74484 (15)	0.0247 (5)
H5	0.2103	−0.1896	0.7973	0.030*
C6	0.1555 (2)	−0.01681 (19)	0.74673 (14)	0.0176 (4)
C7	0.1413 (2)	0.04925 (19)	0.83511 (14)	0.0169 (4)
C8	−0.1527 (2)	0.13023 (18)	0.83944 (13)	0.0152 (4)
C9	−0.2611 (2)	0.06755 (18)	0.89469 (14)	0.0171 (4)
H9	−0.2425	0.0310	0.9499	0.021*
C10	−0.3982 (2)	0.06016 (19)	0.86638 (14)	0.0205 (4)
H10	−0.4706	0.0166	0.9021	0.025*
C11	−0.4279 (3)	0.1172 (2)	0.78530 (14)	0.0224 (5)
H11	−0.5206	0.1123	0.7672	0.027*
C12	−0.3208 (2)	0.1815 (2)	0.73125 (14)	0.0209 (4)
H12	−0.3419	0.2204	0.6772	0.025*
C13	−0.1806 (2)	0.18787 (18)	0.75783 (14)	0.0175 (4)
C14	−0.0645 (3)	0.2544 (2)	0.69667 (15)	0.0232 (5)
C15	0.2483 (3)	0.24962 (19)	0.48932 (14)	0.0194 (4)
C16	0.1234 (3)	0.3396 (2)	0.46486 (16)	0.0274 (5)
H16	0.0445	0.3938	0.5101	0.033*
C17	0.1187 (3)	0.3471 (2)	0.37219 (17)	0.0303 (5)
H17	0.0352	0.4066	0.3552	0.036*
C18	0.2361 (3)	0.2677 (2)	0.30412 (15)	0.0250 (5)
C19	0.3592 (3)	0.1785 (2)	0.33051 (16)	0.0278 (5)
H19	0.4384	0.1247	0.2852	0.033*
C20	0.3662 (3)	0.1682 (2)	0.42303 (15)	0.0268 (5)
H20	0.4485	0.1078	0.4402	0.032*
C21	0.2294 (3)	0.2763 (2)	0.20329 (17)	0.0356 (6)
H21A	0.3194	0.2144	0.1662	0.053*
H21B	0.2377	0.3570	0.1804	0.053*
H21C	0.1267	0.2630	0.1991	0.053*
C22	0.1091 (2)	0.31288 (19)	0.92998 (14)	0.0195 (4)
C23	0.0855 (3)	0.4133 (2)	0.87229 (18)	0.0333 (6)
H23	−0.0072	0.4346	0.8492	0.040*
C24	0.2022 (3)	0.4814 (2)	0.8495 (2)	0.0395 (6)
H24	0.1867	0.5494	0.8111	0.047*
C25	0.3419 (3)	0.4508 (2)	0.88264 (18)	0.0324 (6)
C26	0.3612 (3)	0.3508 (2)	0.94126 (17)	0.0292 (5)
H26	0.4532	0.3301	0.9650	0.035*
C27	0.2464 (3)	0.2812 (2)	0.96518 (15)	0.0239 (5)
H27	0.2611	0.2139	1.0044	0.029*
C28	0.4722 (3)	0.5229 (3)	0.8558 (2)	0.0508 (8)
H28A	0.4406	0.5887	0.8150	0.076*
H28B	0.5760	0.4687	0.8241	0.076*
H28C	0.4827	0.5571	0.9113	0.076*
O8	0.4362 (4)	0.5295 (3)	0.47416 (19)	0.0648 (8)	0.50
H8	0.3384	0.5054	0.5060	0.097*	0.50
C29	0.4362 (4)	0.5295 (3)	0.47416 (19)	0.0648 (8)	0.50
C30	0.4689 (5)	0.4823 (4)	0.3786 (3)	0.0253 (9)	0.50
H30A	0.3799	0.5254	0.3529	0.038*	0.50
H30B	0.4762	0.3951	0.3790	0.038*	0.50
H30C	0.5707	0.4971	0.3408	0.038*	0.50
O7	0.3037 (5)	0.5905 (3)	0.5167 (3)	0.0489 (10)	0.50
N1	0.0986 (2)	0.18137 (16)	0.66594 (12)	0.0186 (4)
N2	−0.00829 (19)	0.13646 (15)	0.86839 (11)	0.0164 (4)
O1	0.25131 (17)	0.03120 (13)	0.87404 (10)	0.0209 (3)
O2	−0.1071 (2)	0.36032 (16)	0.67434 (14)	0.0436 (5)
O3	0.2235 (2)	0.36337 (15)	0.64412 (11)	0.0315 (4)
O4	0.40207 (18)	0.15004 (16)	0.61277 (11)	0.0303 (4)
O5	−0.20005 (18)	0.30902 (15)	0.96957 (11)	0.0310 (4)
O6	−0.0125 (2)	0.15277 (15)	1.04057 (10)	0.0287 (4)
S1	0.25694 (6)	0.24198 (5)	0.60663 (4)	0.02218 (14)
S2	−0.04108 (6)	0.22883 (5)	0.96340 (4)	0.02004 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0126 (10)	0.0221 (11)	0.0204 (10)	−0.0069 (8)	−0.0035 (8)	0.0043 (8)
C2	0.0239 (11)	0.0320 (12)	0.0178 (10)	−0.0102 (10)	−0.0045 (9)	0.0051 (9)
C3	0.0425 (14)	0.0328 (13)	0.0190 (11)	−0.0085 (11)	−0.0029 (10)	−0.0051 (9)
C4	0.0491 (16)	0.0214 (12)	0.0251 (12)	−0.0001 (11)	−0.0009 (11)	−0.0022 (9)
C5	0.0255 (12)	0.0243 (12)	0.0178 (10)	0.0008 (9)	−0.0021 (9)	0.0038 (9)
C6	0.0110 (9)	0.0225 (11)	0.0175 (10)	−0.0033 (8)	−0.0022 (8)	0.0030 (8)
C7	0.0134 (10)	0.0202 (10)	0.0186 (10)	−0.0086 (8)	−0.0038 (8)	0.0069 (8)
C8	0.0105 (9)	0.0169 (10)	0.0200 (10)	−0.0036 (8)	−0.0066 (8)	−0.0015 (8)
C9	0.0145 (10)	0.0211 (10)	0.0168 (10)	−0.0056 (8)	−0.0051 (8)	0.0009 (8)
C10	0.0139 (10)	0.0264 (11)	0.0235 (11)	−0.0101 (9)	−0.0042 (8)	0.0016 (9)
C11	0.0160 (10)	0.0329 (12)	0.0224 (11)	−0.0096 (9)	−0.0085 (8)	0.0006 (9)
C12	0.0176 (10)	0.0272 (12)	0.0196 (10)	−0.0046 (9)	−0.0093 (8)	0.0036 (8)
C13	0.0132 (10)	0.0168 (10)	0.0223 (10)	−0.0036 (8)	−0.0049 (8)	0.0013 (8)
C14	0.0197 (11)	0.0251 (12)	0.0279 (11)	−0.0085 (9)	−0.0097 (9)	0.0078 (9)
C15	0.0216 (11)	0.0240 (11)	0.0187 (10)	−0.0144 (9)	−0.0092 (8)	0.0095 (8)
C16	0.0365 (13)	0.0183 (11)	0.0285 (12)	−0.0044 (10)	−0.0131 (10)	0.0013 (9)
C17	0.0431 (14)	0.0190 (11)	0.0345 (13)	−0.0049 (10)	−0.0237 (11)	0.0059 (9)
C18	0.0340 (13)	0.0258 (12)	0.0243 (11)	−0.0173 (10)	−0.0149 (10)	0.0079 (9)
C19	0.0229 (11)	0.0371 (13)	0.0230 (11)	−0.0092 (10)	−0.0043 (9)	0.0027 (10)
C20	0.0164 (11)	0.0371 (13)	0.0271 (12)	−0.0072 (10)	−0.0075 (9)	0.0094 (10)
C21	0.0499 (16)	0.0386 (14)	0.0274 (12)	−0.0171 (12)	−0.0204 (11)	0.0054 (10)
C22	0.0189 (10)	0.0189 (10)	0.0235 (10)	−0.0088 (8)	−0.0062 (8)	−0.0018 (8)
C23	0.0315 (13)	0.0292 (13)	0.0463 (15)	−0.0118 (11)	−0.0201 (11)	0.0097 (11)
C24	0.0443 (16)	0.0269 (13)	0.0523 (16)	−0.0172 (12)	−0.0155 (13)	0.0126 (12)
C25	0.0271 (13)	0.0231 (12)	0.0455 (15)	−0.0120 (10)	−0.0002 (11)	−0.0082 (10)
C26	0.0215 (11)	0.0292 (12)	0.0418 (14)	−0.0104 (10)	−0.0111 (10)	−0.0081 (10)
C27	0.0258 (12)	0.0239 (11)	0.0278 (11)	−0.0102 (9)	−0.0127 (9)	−0.0005 (9)
C28	0.0350 (15)	0.0342 (15)	0.081 (2)	−0.0223 (13)	0.0026 (14)	−0.0080 (14)
O8	0.0622 (18)	0.081 (2)	0.0552 (17)	−0.0210 (16)	−0.0189 (14)	−0.0014 (15)
C29	0.0622 (18)	0.081 (2)	0.0552 (17)	−0.0210 (16)	−0.0189 (14)	−0.0014 (15)
C30	0.020 (2)	0.024 (2)	0.031 (2)	−0.0067 (18)	−0.0053 (18)	0.0017 (18)
O7	0.042 (2)	0.036 (2)	0.048 (2)	0.0165 (18)	0.0000 (18)	−0.0187 (18)
N1	0.0158 (9)	0.0224 (9)	0.0197 (9)	−0.0085 (7)	−0.0056 (7)	0.0066 (7)
N2	0.0119 (8)	0.0215 (9)	0.0184 (8)	−0.0061 (7)	−0.0063 (6)	−0.0018 (7)
O1	0.0144 (7)	0.0274 (8)	0.0258 (8)	−0.0099 (6)	−0.0107 (6)	0.0090 (6)
O2	0.0271 (9)	0.0274 (10)	0.0717 (13)	−0.0078 (7)	−0.0091 (9)	0.0254 (9)
O3	0.0396 (10)	0.0400 (10)	0.0240 (8)	−0.0280 (8)	−0.0070 (7)	0.0044 (7)
O4	0.0172 (8)	0.0515 (11)	0.0263 (8)	−0.0142 (7)	−0.0102 (6)	0.0159 (7)
O5	0.0176 (8)	0.0341 (9)	0.0403 (10)	−0.0046 (7)	−0.0046 (7)	−0.0164 (7)
O6	0.0370 (9)	0.0392 (9)	0.0173 (8)	−0.0229 (8)	−0.0071 (7)	0.0027 (7)
S1	0.0199 (3)	0.0336 (3)	0.0191 (3)	−0.0163 (2)	−0.0078 (2)	0.0087 (2)
S2	0.0173 (3)	0.0259 (3)	0.0197 (3)	−0.0102 (2)	−0.0041 (2)	−0.0039 (2)

C1—C2	1.387 (3)	C18—C21	1.507 (3)
C1—C6	1.393 (3)	C19—C20	1.385 (3)
C1—N1	1.451 (3)	C19—H19	0.9300
C2—C3	1.376 (3)	C20—H20	0.9300
C2—H2	0.9300	C21—H21A	0.9600
C3—C4	1.386 (3)	C21—H21B	0.9600
C3—H3	0.9300	C21—H21C	0.9600
C4—C5	1.387 (3)	C22—C23	1.381 (3)
C4—H4	0.9300	C22—C27	1.386 (3)
C5—C6	1.390 (3)	C22—S2	1.751 (2)
C5—H5	0.9300	C23—C24	1.382 (3)
C6—C7	1.496 (3)	C23—H23	0.9300
C7—O1	1.214 (2)	C24—C25	1.386 (4)
C7—N2	1.392 (3)	C24—H24	0.9300
C8—C9	1.383 (3)	C25—C26	1.382 (3)
C8—C13	1.390 (3)	C25—C28	1.511 (3)
C8—N2	1.450 (2)	C26—C27	1.382 (3)
C9—C10	1.388 (3)	C26—H26	0.9300
C9—H9	0.9300	C27—H27	0.9300
C10—C11	1.385 (3)	C28—H28A	0.9600
C10—H10	0.9300	C28—H28B	0.9600
C11—C12	1.380 (3)	C28—H28C	0.9600
C11—H11	0.9300	O8—O7	1.199 (4)
C12—C13	1.397 (3)	O8—C30	1.465 (5)
C12—H12	0.9300	O8—O8i	1.510 (5)
C13—C14	1.488 (3)	O8—H8	0.9518
C14—O2	1.203 (3)	C30—H30A	0.9600
C14—N1	1.407 (3)	C30—H30B	0.9600
C15—C20	1.382 (3)	C30—H30C	0.9600
C15—C16	1.391 (3)	O7—H8	0.9283
C15—S1	1.755 (2)	N1—S1	1.7000 (17)
C16—C17	1.381 (3)	N2—S2	1.7052 (17)
C16—H16	0.9300	O3—S1	1.4215 (17)
C17—C18	1.384 (3)	O4—S1	1.4287 (16)
C17—H17	0.9300	O5—S2	1.4229 (16)
C18—C19	1.389 (3)	O6—S2	1.4260 (16)
C2—C1—C6	120.69 (19)	C18—C21—H21B	109.5
C2—C1—N1	119.37 (18)	H21A—C21—H21B	109.5
C6—C1—N1	119.95 (18)	C18—C21—H21C	109.5
C3—C2—C1	119.8 (2)	H21A—C21—H21C	109.5
C3—C2—H2	120.1	H21B—C21—H21C	109.5
C1—C2—H2	120.1	C23—C22—C27	120.87 (19)
C2—C3—C4	120.2 (2)	C23—C22—S2	119.55 (16)
C2—C3—H3	119.9	C27—C22—S2	119.52 (16)
C4—C3—H3	119.9	C22—C23—C24	118.8 (2)
C3—C4—C5	120.1 (2)	C22—C23—H23	120.6
C3—C4—H4	119.9	C24—C23—H23	120.6
C5—C4—H4	119.9	C23—C24—C25	121.6 (2)
C4—C5—C6	120.2 (2)	C23—C24—H24	119.2
C4—C5—H5	119.9	C25—C24—H24	119.2
C6—C5—H5	119.9	C26—C25—C24	118.4 (2)
C5—C6—C1	118.95 (19)	C26—C25—C28	119.8 (2)
C5—C6—C7	119.38 (17)	C24—C25—C28	121.8 (2)
C1—C6—C7	121.67 (18)	C27—C26—C25	121.2 (2)
O1—C7—N2	122.21 (19)	C27—C26—H26	119.4
O1—C7—C6	123.48 (18)	C25—C26—H26	119.4
N2—C7—C6	114.29 (16)	C26—C27—C22	119.2 (2)
C9—C8—C13	121.32 (17)	C26—C27—H27	120.4
C9—C8—N2	118.90 (17)	C22—C27—H27	120.4
C13—C8—N2	119.78 (17)	C25—C28—H28A	109.5
C8—C9—C10	118.93 (18)	C25—C28—H28B	109.5
C8—C9—H9	120.5	H28A—C28—H28B	109.5
C10—C9—H9	120.5	C25—C28—H28C	109.5
C11—C10—C9	120.46 (19)	H28A—C28—H28C	109.5
C11—C10—H10	119.8	H28B—C28—H28C	109.5
C9—C10—H10	119.8	O7—O8—C30	122.8 (3)
C12—C11—C10	120.37 (18)	O7—O8—O8i	119.8 (4)
C12—C11—H11	119.8	C30—O8—O8i	115.6 (3)
C10—C11—H11	119.8	O7—O8—H8	49.5
C11—C12—C13	119.90 (18)	C30—O8—H8	102.6
C11—C12—H12	120.0	O8i—O8—H8	106.1
C13—C12—H12	120.0	O8—C30—H30A	108.4
C8—C13—C12	119.01 (18)	O8—C30—H30B	110.4
C8—C13—C14	122.23 (17)	H30A—C30—H30B	109.5
C12—C13—C14	118.75 (18)	O8—C30—H30C	109.6
O2—C14—N1	123.2 (2)	H30A—C30—H30C	109.5
O2—C14—C13	123.0 (2)	H30B—C30—H30C	109.5
N1—C14—C13	113.85 (17)	O8—O7—H8	51.3
C20—C15—C16	121.33 (19)	C14—N1—C1	119.97 (16)
C20—C15—S1	119.85 (16)	C14—N1—S1	122.16 (14)
C16—C15—S1	118.81 (17)	C1—N1—S1	116.64 (13)
C17—C16—C15	118.7 (2)	C7—N2—C8	120.46 (16)
C17—C16—H16	120.6	C7—N2—S2	120.92 (13)
C15—C16—H16	120.6	C8—N2—S2	116.82 (13)
C16—C17—C18	121.2 (2)	O3—S1—O4	120.61 (10)
C16—C17—H17	119.4	O3—S1—N1	106.68 (9)
C18—C17—H17	119.4	O4—S1—N1	104.34 (9)
C17—C18—C19	118.8 (2)	O3—S1—C15	110.00 (10)
C17—C18—C21	120.8 (2)	O4—S1—C15	108.42 (10)
C19—C18—C21	120.4 (2)	N1—S1—C15	105.68 (9)
C20—C19—C18	121.2 (2)	O5—S2—O6	119.90 (10)
C20—C19—H19	119.4	O5—S2—N2	103.20 (8)
C18—C19—H19	119.4	O6—S2—N2	109.03 (9)
C15—C20—C19	118.7 (2)	O5—S2—C22	109.77 (10)
C15—C20—H20	120.7	O6—S2—C22	109.15 (10)
C19—C20—H20	120.7	N2—S2—C22	104.62 (9)
C18—C21—H21A	109.5
C6—C1—C2—C3	0.1 (3)	C24—C25—C26—C27	1.2 (4)
N1—C1—C2—C3	179.86 (19)	C28—C25—C26—C27	−178.4 (2)
C1—C2—C3—C4	−1.2 (4)	C25—C26—C27—C22	−0.4 (3)
C2—C3—C4—C5	0.7 (4)	C23—C22—C27—C26	−0.5 (3)
C3—C4—C5—C6	0.8 (4)	S2—C22—C27—C26	−177.60 (17)
C4—C5—C6—C1	−1.8 (3)	O2—C14—N1—C1	−158.1 (2)
C4—C5—C6—C7	177.1 (2)	C13—C14—N1—C1	20.7 (3)
C2—C1—C6—C5	1.4 (3)	O2—C14—N1—S1	8.8 (3)
N1—C1—C6—C5	−178.39 (18)	C13—C14—N1—S1	−172.40 (14)
C2—C1—C6—C7	−177.50 (18)	C2—C1—N1—C14	92.5 (2)
N1—C1—C6—C7	2.7 (3)	C6—C1—N1—C14	−87.8 (2)
C5—C6—C7—O1	57.8 (3)	C2—C1—N1—S1	−75.2 (2)
C1—C6—C7—O1	−123.3 (2)	C6—C1—N1—S1	104.62 (18)
C5—C6—C7—N2	−123.7 (2)	O1—C7—N2—C8	−160.90 (18)
C1—C6—C7—N2	55.2 (2)	C6—C7—N2—C8	20.6 (2)
C13—C8—C9—C10	1.5 (3)	O1—C7—N2—S2	3.3 (3)
N2—C8—C9—C10	−179.16 (17)	C6—C7—N2—S2	−175.14 (13)
C8—C9—C10—C11	−1.6 (3)	C9—C8—N2—C7	93.3 (2)
C9—C10—C11—C12	0.5 (3)	C13—C8—N2—C7	−87.3 (2)
C10—C11—C12—C13	0.7 (3)	C9—C8—N2—S2	−71.5 (2)
C9—C8—C13—C12	−0.3 (3)	C13—C8—N2—S2	107.86 (18)
N2—C8—C13—C12	−179.68 (18)	C14—N1—S1—O3	34.98 (18)
C9—C8—C13—C14	−179.19 (19)	C1—N1—S1—O3	−157.71 (14)
N2—C8—C13—C14	1.5 (3)	C14—N1—S1—O4	163.68 (16)
C11—C12—C13—C8	−0.8 (3)	C1—N1—S1—O4	−29.01 (16)
C11—C12—C13—C14	178.13 (19)	C14—N1—S1—C15	−82.08 (18)
C8—C13—C14—O2	−125.5 (2)	C1—N1—S1—C15	85.23 (15)
C12—C13—C14—O2	55.7 (3)	C20—C15—S1—O3	137.50 (17)
C8—C13—C14—N1	55.7 (3)	C16—C15—S1—O3	−41.45 (19)
C12—C13—C14—N1	−123.1 (2)	C20—C15—S1—O4	3.7 (2)
C20—C15—C16—C17	−0.2 (3)	C16—C15—S1—O4	−175.27 (16)
S1—C15—C16—C17	178.73 (17)	C20—C15—S1—N1	−107.71 (18)
C15—C16—C17—C18	−0.5 (3)	C16—C15—S1—N1	73.34 (18)
C16—C17—C18—C19	0.6 (3)	C7—N2—S2—O5	175.75 (15)
C16—C17—C18—C21	179.7 (2)	C8—N2—S2—O5	−19.48 (16)
C17—C18—C19—C20	−0.1 (3)	C7—N2—S2—O6	−55.75 (17)
C21—C18—C19—C20	−179.2 (2)	C8—N2—S2—O6	109.02 (15)
C16—C15—C20—C19	0.7 (3)	C7—N2—S2—C22	60.89 (17)
S1—C15—C20—C19	−178.24 (17)	C8—N2—S2—C22	−134.34 (15)
C18—C19—C20—C15	−0.5 (3)	C23—C22—S2—O5	−31.5 (2)
C27—C22—C23—C24	0.5 (4)	C27—C22—S2—O5	145.58 (17)
S2—C22—C23—C24	177.5 (2)	C23—C22—S2—O6	−164.81 (18)
C22—C23—C24—C25	0.4 (4)	C27—C22—S2—O6	12.3 (2)
C23—C24—C25—C26	−1.3 (4)	C23—C22—S2—N2	78.6 (2)
C23—C24—C25—C28	178.3 (3)	C27—C22—S2—N2	−104.27 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O3	0.95	2.66	3.460 (3)	142
C30—H30C···O3i	0.96	2.71	3.473 (5)	136
C16—H16···O2	0.93	2.49	3.190 (3)	132
C11—H11···O4ii	0.93	2.54	3.241 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O3	0.95	2.66	3.460 (3)	142
C30—H30C⋯O3i	0.96	2.71	3.473 (5)	136
C16—H16⋯O2	0.93	2.49	3.190 (3)	132
C11—H11⋯O4ii	0.93	2.54	3.241 (2)	133

Symmetry codes: (i) ; (ii) .