Dimorphism and inclusion compounds of N,N'-di(benzenesulfonyl)-p-phenylenediamine

Crystal structures of a new polymorph of N,N'-(p-phenyl­ene)bis(benzenesulfonamide) (C₁₈H₁₆N₂O₄S₂) and of two inclusion compounds with acetone [(CH₃)₂CO] and dimethylsulfoxide [2(CH₃)₂SO], respectively, have been determined at 150 K. For a more reliable comparison, the structure of the already known polymorph of N,N'-di(benzenesulfonyl)-p-phenylenediamine has been redetermined under identical conditions. In addition, the phase transformation behavior has been examined by differential scanning calorimetry and the crystallization conditions of both polymorphs including their formation by weathering of the inclusion compounds were investigated.

Computing details

For all compounds, program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993).

(bock497)

Crystal data

C18H16N2O4S2	F(000) = 404
Mr = 388.45	Dx = 1.449 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 90 reflections
a = 9.0603 (11) Å	θ = 7.5–20.5°
b = 10.6109 (13) Å	µ = 0.33 mm^−1
c = 9.4613 (14) Å	T = 150 K
β = 101.893 (6)°	Block, colourless
V = 890.1 (2) Å^3	0.65 × 0.50 × 0.45 mm
Z = 2

Data collection

Siemens P4 four circle diffractometer	Rint = 0.014
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.3°
Graphite monochromator	h = 0→12
ω scan	k = 0→14
2712 measured reflections	l = −12→12
2571 independent reflections	4 standard reflections every 100 reflections
2214 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters not defined?
wR(F^2) = 0.107	Calculated w = 1/[σ^2(Fo^2) + (0.053P)^2 + 0.4032P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2571 reflections	Δρmax = 0.41 e Å^−3
123 parameters	Δρmin = −0.33 e Å^−3
0 restraints	Extinction correction: SHELXL93, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0076 (25)

Special details

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.19689 (4)	0.06385 (3)	0.40541 (4)	0.02635 (12)
N1	0.03348 (14)	0.05207 (12)	0.29630 (13)	0.0277 (2)
H1N	−0.024 (2)	0.014 (2)	0.335 (2)	0.044 (6)*
O1	0.16160 (13)	0.07952 (10)	0.54561 (11)	0.0315 (2)
O2	0.28135 (14)	0.15882 (11)	0.35154 (13)	0.0381 (3)
C1	0.0209 (2)	0.02470 (13)	0.14668 (14)	0.0258 (3)
C2	0.0831 (2)	0.10503 (13)	0.0582 (2)	0.0292 (3)
H2	0.1396 (2)	0.17671 (13)	0.0979 (2)	0.035*
C3	−0.0618 (2)	−0.07955 (13)	0.0882 (2)	0.0290 (3)
H3	−0.1042 (2)	−0.13394 (13)	0.1490 (2)	0.035*
C10	0.2890 (2)	−0.08114 (14)	0.4015 (2)	0.0302 (3)
C11	0.4110 (2)	−0.0897 (2)	0.3357 (2)	0.0493 (5)
H11	0.4474 (2)	−0.0174 (2)	0.2944 (2)	0.059*
C12	0.4795 (3)	−0.2062 (3)	0.3311 (3)	0.0692 (7)
H12	0.5628 (3)	−0.2145 (3)	0.2852 (3)	0.083*
C13	0.4266 (3)	−0.3097 (2)	0.3931 (3)	0.0639 (7)
H13	0.4740 (3)	−0.3892 (2)	0.3891 (3)	0.077*
C14	0.3069 (3)	−0.3001 (2)	0.4605 (3)	0.0580 (6)
H14	0.2725 (3)	−0.3720 (2)	0.5039 (3)	0.070*
C15	0.2365 (2)	−0.1849 (2)	0.4649 (2)	0.0445 (4)
H15	0.1531 (2)	−0.1771 (2)	0.5109 (2)	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0313 (2)	0.0253 (2)	0.0254 (2)	−0.00404 (12)	0.01263 (12)	−0.00185 (12)
N1	0.0299 (6)	0.0298 (6)	0.0260 (6)	−0.0015 (5)	0.0118 (4)	0.0013 (4)
O1	0.0401 (6)	0.0316 (5)	0.0264 (5)	−0.0043 (4)	0.0150 (4)	−0.0055 (4)
O2	0.0429 (6)	0.0367 (6)	0.0373 (6)	−0.0136 (5)	0.0146 (5)	0.0026 (5)
C1	0.0305 (7)	0.0238 (6)	0.0253 (6)	0.0006 (5)	0.0109 (5)	0.0029 (5)
C2	0.0369 (7)	0.0227 (6)	0.0297 (7)	−0.0054 (5)	0.0111 (6)	0.0027 (5)
C3	0.0360 (7)	0.0251 (6)	0.0281 (6)	−0.0046 (5)	0.0120 (5)	0.0052 (5)
C10	0.0282 (6)	0.0336 (7)	0.0291 (7)	0.0016 (5)	0.0065 (5)	−0.0062 (5)
C11	0.0425 (9)	0.0676 (13)	0.0423 (9)	0.0104 (9)	0.0189 (8)	−0.0044 (9)
C12	0.0525 (12)	0.099 (2)	0.0575 (13)	0.0324 (13)	0.0141 (10)	−0.0212 (13)
C13	0.0599 (13)	0.0551 (13)	0.0669 (14)	0.0274 (11)	−0.0097 (11)	−0.0233 (11)
C14	0.0562 (12)	0.0344 (9)	0.0768 (15)	0.0076 (8)	−0.0020 (11)	−0.0058 (9)
C15	0.0406 (9)	0.0310 (8)	0.0627 (12)	0.0011 (7)	0.0126 (8)	0.0010 (8)

Geometric parameters (Å, º)

S1—O2	1.4218 (11)	C3—C2^i	1.386 (2)
S1—O1	1.4367 (10)	C10—C11	1.378 (2)
S1—N1	1.6259 (13)	C10—C15	1.384 (2)
S1—C10	1.755 (2)	C11—C12	1.388 (3)
N1—C1	1.426 (2)	C12—C13	1.377 (4)
C1—C3	1.386 (2)	C13—C14	1.371 (4)
C1—C2	1.392 (2)	C14—C15	1.383 (3)
C2—C3^i	1.386 (2)
O2—S1—O1	119.18 (7)	C3^i—C2—C1	119.43 (13)
O2—S1—N1	108.29 (7)	C2^i—C3—C1	120.49 (12)
O1—S1—N1	104.38 (7)	C11—C10—C15	121.5 (2)
O2—S1—C10	108.68 (8)	C11—C10—S1	119.78 (14)
O1—S1—C10	108.57 (7)	C15—C10—S1	118.73 (12)
N1—S1—C10	107.11 (7)	C10—C11—C12	118.6 (2)
C1—N1—S1	121.44 (10)	C13—C12—C11	120.0 (2)
C3—C1—C2	120.08 (13)	C14—C13—C12	121.1 (2)
C3—C1—N1	118.99 (12)	C13—C14—C15	119.6 (2)
C2—C1—N1	120.83 (13)	C14—C15—C10	119.2 (2)
O2—S1—N1—C1	57.40 (13)	O2—S1—C10—C15	172.49 (14)
O1—S1—N1—C1	−174.66 (11)	O1—S1—C10—C15	41.5 (2)
C10—S1—N1—C1	−59.64 (12)	N1—S1—C10—C15	−70.72 (15)
S1—N1—C1—C3	123.22 (13)	C15—C10—C11—C12	1.4 (3)
S1—N1—C1—C2	−60.5 (2)	S1—C10—C11—C12	−178.5 (2)
C3—C1—C2—C3^i	−0.2 (2)	C10—C11—C12—C13	−0.8 (3)
N1—C1—C2—C3^i	−176.44 (14)	C11—C12—C13—C14	−0.3 (4)
C2—C1—C3—C2^i	0.2 (2)	C12—C13—C14—C15	0.8 (3)
N1—C1—C3—C2^i	176.51 (14)	C13—C14—C15—C10	−0.3 (3)
O2—S1—C10—C11	−7.6 (2)	C11—C10—C15—C14	−0.8 (3)
O1—S1—C10—C11	−138.69 (14)	S1—C10—C15—C14	179.0 (2)
N1—S1—C10—C11	109.13 (15)

Symmetry code: (i) −x, −y, −z.

(bock336)

Crystal data

C18H16N2O4S2	F(000) = 404
Mr = 388.45	Dx = 1.442 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 65 reflections
a = 10.6449 (6) Å	θ = 8.5–21°
b = 6.4510 (4) Å	µ = 0.32 mm^−1
c = 13.1061 (7) Å	T = 150 K
β = 96.195 (4)°	Block, colourless
V = 894.74 (9) Å^3	0.60 × 0.50 × 0.40 mm
Z = 2

Data collection

Siemens P4 four circle diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 2.3°
Graphite monochromator	h = 0→13
ω scan	k = 0→8
2052 measured reflections	l = −16→16
1949 independent reflections	4 standard reflections every 100 reflections
1768 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters not defined?
S = 1.03	Calculated w = 1/[σ^2(Fo^2) + (0.046P)^2 + 0.4377P] where P = (Fo^2 + 2Fc^2)/3
1949 reflections	(Δ/σ)max < 0.001
122 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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 (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.07891 (3)	−0.23748 (5)	−0.24886 (3)	0.02054 (13)
O1	−0.17907 (11)	−0.17754 (18)	−0.18943 (8)	0.0295 (3)
O2	0.00405 (11)	−0.08355 (17)	−0.28258 (9)	0.0298 (3)
N1	−0.15026 (11)	−0.35186 (19)	−0.35074 (9)	0.0202 (3)
H1N	−0.2050 (18)	−0.442 (3)	−0.3321 (15)	0.031 (5)*
C1	−0.07293 (13)	−0.4289 (2)	−0.42612 (10)	0.0184 (3)
C2	−0.03847 (14)	−0.2944 (2)	−0.50061 (11)	0.0225 (3)
H2	−0.0649	−0.1537	−0.5008	0.027*
C3	−0.03471 (14)	−0.6352 (2)	−0.42482 (11)	0.0219 (3)
H3	−0.0584	−0.7270	−0.3735	0.026*
C10	0.01136 (13)	−0.4294 (2)	−0.17907 (11)	0.0213 (3)
C11	0.14201 (15)	−0.4314 (3)	−0.17670 (12)	0.0309 (4)
H11	0.1849	−0.3257	−0.2096	0.037*
C12	0.20876 (16)	−0.5926 (3)	−0.12480 (14)	0.0390 (4)
H12	0.2982	−0.5971	−0.1222	0.047*
C13	0.14586 (19)	−0.7453 (3)	−0.07722 (14)	0.0397 (4)
H13	0.1923	−0.8545	−0.0422	0.048*
C14	0.01509 (18)	−0.7406 (3)	−0.08010 (13)	0.0351 (4)
H14	−0.0277	−0.8464	−0.0471	0.042*
C15	−0.05286 (15)	−0.5821 (2)	−0.13098 (12)	0.0266 (3)
H15	−0.1423	−0.5777	−0.1330	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0224 (2)	0.0182 (2)	0.0219 (2)	0.00205 (12)	0.00632 (13)	−0.00142 (12)
O1	0.0311 (6)	0.0304 (6)	0.0289 (6)	0.0110 (5)	0.0114 (5)	−0.0013 (5)
O2	0.0356 (6)	0.0211 (5)	0.0336 (6)	−0.0061 (5)	0.0078 (5)	−0.0018 (4)
N1	0.0181 (6)	0.0218 (6)	0.0214 (6)	−0.0017 (5)	0.0053 (5)	0.0008 (5)
C1	0.0172 (6)	0.0206 (7)	0.0174 (6)	−0.0018 (5)	0.0018 (5)	0.0000 (5)
C2	0.0275 (7)	0.0160 (6)	0.0243 (7)	0.0014 (6)	0.0047 (6)	0.0025 (5)
C3	0.0264 (7)	0.0191 (6)	0.0210 (6)	−0.0019 (6)	0.0059 (5)	0.0046 (5)
C10	0.0215 (7)	0.0229 (7)	0.0195 (6)	0.0033 (5)	0.0016 (5)	−0.0037 (5)
C11	0.0228 (8)	0.0410 (9)	0.0294 (8)	0.0010 (7)	0.0053 (6)	−0.0029 (7)
C12	0.0248 (8)	0.0568 (12)	0.0344 (9)	0.0146 (8)	−0.0015 (7)	−0.0078 (8)
C13	0.0451 (10)	0.0401 (10)	0.0312 (8)	0.0178 (8)	−0.0078 (8)	−0.0033 (7)
C14	0.0439 (10)	0.0284 (8)	0.0310 (8)	0.0005 (7)	−0.0055 (7)	0.0040 (7)
C15	0.0256 (7)	0.0270 (7)	0.0264 (7)	−0.0004 (6)	−0.0004 (6)	0.0005 (6)

Geometric parameters (Å, º)

S1—O2	1.4303 (11)	C3—C2^i	1.390 (2)
S1—O1	1.4395 (11)	C10—C11	1.388 (2)
S1—N1	1.6388 (13)	C10—C15	1.389 (2)
S1—C10	1.7614 (15)	C11—C12	1.394 (3)
N1—C1	1.441 (2)	C12—C13	1.378 (3)
C1—C2	1.385 (2)	C13—C14	1.389 (3)
C1—C3	1.391 (2)	C14—C15	1.382 (2)
C2—C3^i	1.390 (2)
O2—S1—O1	119.92 (7)	C1—C2—C3^i	120.12 (13)
O2—S1—N1	107.95 (7)	C2^i—C3—C1	119.29 (13)
O1—S1—N1	104.87 (7)	C11—C10—C15	121.62 (14)
O2—S1—C10	109.14 (7)	C11—C10—S1	120.51 (12)
O1—S1—C10	107.59 (7)	C15—C10—S1	117.81 (11)
N1—S1—C10	106.59 (7)	C10—C11—C12	118.4 (2)
C1—N1—S1	117.72 (9)	C13—C12—C11	120.5 (2)
C2—C1—C3	120.59 (13)	C12—C13—C14	120.5 (2)
C2—C1—N1	118.78 (13)	C15—C14—C13	120.0 (2)
C3—C1—N1	120.63 (12)	C14—C15—C10	119.1 (2)
O2—S1—N1—C1	50.71 (12)	O2—S1—C10—C15	173.69 (11)
O1—S1—N1—C1	179.65 (10)	O1—S1—C10—C15	42.09 (13)
C10—S1—N1—C1	−66.43 (12)	N1—S1—C10—C15	−69.96 (13)
S1—N1—C1—C2	−85.08 (14)	C15—C10—C11—C12	0.3 (2)
S1—N1—C1—C3	95.62 (14)	S1—C10—C11—C12	−176.74 (12)
C3—C1—C2—C3^i	0.1 (2)	C10—C11—C12—C13	0.0 (3)
N1—C1—C2—C3^i	−179.16 (13)	C11—C12—C13—C14	−0.1 (3)
C2—C1—C3—C2^i	−0.1 (2)	C12—C13—C14—C15	0.0 (3)
N1—C1—C3—C2^i	179.15 (13)	C13—C14—C15—C10	0.2 (2)
O2—S1—C10—C11	−9.14 (14)	C11—C10—C15—C14	−0.4 (2)
O1—S1—C10—C11	−140.75 (13)	S1—C10—C15—C14	176.71 (12)
N1—S1—C10—C11	107.20 (13)

Symmetry code: (i) −x, −y−1, −z−1.

(bock503)

Crystal data

C18H16N2O4S2·CO(CH3)2	F(000) = 936
Mr = 446.53	Dx = 1.443 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 90 reflections
a = 17.503 (2) Å	θ = 10–19°
b = 7.7310 (9) Å	µ = 0.30 mm^−1
c = 15.188 (2) Å	T = 150 K
V = 2055.1 (4) Å^3	Block, colourless
Z = 4	0.70 × 0.65 × 0.40 mm

Data collection

Siemens P4 four circle diffractometer	Rint = 0.020
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.3°
Graphite monochromator	h = −1→21
ω scan	k = −1→9
2658 measured reflections	l = −1→18
2016 independent reflections	4 standard reflections every 100 reflections
1564 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters not defined?
wR(F^2) = 0.114	Calculated w = 1/[σ^2(Fo^2) + (0.0446P)^2 + 2.2606P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2013 reflections	Δρmax = 0.39 e Å^−3
144 parameters	Δρmin = −0.33 e Å^−3
3 restraints	Extinction correction: SHELXL93, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (7)

Special details

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 on F² for ALL reflections except for 3 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.16553 (3)	0.14541 (7)	0.50034 (4)	0.0244 (2)
O1	0.24182 (9)	0.1232 (2)	0.46828 (12)	0.0342 (4)
O2	0.10893 (9)	0.0208 (2)	0.47845 (11)	0.0313 (4)
N1	0.13919 (10)	0.3334 (2)	0.46212 (13)	0.0224 (4)
H1N	0.1759 (14)	0.401 (3)	0.4564 (16)	0.024 (7)*
C1	0.06814 (11)	0.4140 (3)	0.48302 (13)	0.0201 (4)
C2	0.06696 (12)	0.5911 (3)	0.4939 (2)	0.0257 (5)
H2	0.11325 (12)	0.6547 (3)	0.4896 (2)	0.031*
C3	0.00039 (13)	0.3229 (3)	0.4891 (2)	0.0280 (5)
H3	0.00027 (13)	0.2009 (3)	0.4816 (2)	0.034*
C10	0.16958 (14)	0.1617 (3)	0.6154 (2)	0.0310 (6)
C11	0.1123 (2)	0.0894 (4)	0.6663 (2)	0.0403 (6)
H11	0.0704 (2)	0.0321 (4)	0.6394 (2)	0.048*
C12	0.1170 (2)	0.1018 (4)	0.7566 (2)	0.0561 (9)
H12	0.0780 (2)	0.0535 (4)	0.7925 (2)	0.067*
C13	0.1782 (2)	0.1838 (4)	0.7948 (2)	0.0636 (10)
H13	0.1814 (2)	0.1909 (4)	0.8572 (2)	0.076*
C14	0.2345 (2)	0.2552 (4)	0.7444 (2)	0.0612 (10)
H14	0.2762 (2)	0.3126 (4)	0.7718 (2)	0.073*
C15	0.2311 (2)	0.2443 (4)	0.6536 (2)	0.0451 (7)
H15	0.2704 (2)	0.2929 (4)	0.6181 (2)	0.054*
C20	0.5000	0.1442 (4)	0.7500	0.0374 (9)
O3	0.5259 (7)	0.2894 (11)	0.7307 (8)	0.043 (2)*	0.25
C21	0.4197 (3)	0.1024 (8)	0.7301 (4)	0.0487 (14)*	0.50
H21A	0.4085 (3)	−0.0160 (8)	0.7493 (4)	0.073*	0.50
H21B	0.4110 (3)	0.1120 (8)	0.6665 (4)	0.073*	0.50
H21C	0.3861 (3)	0.1834 (8)	0.7612 (4)	0.073*	0.50
O3'	0.4786 (7)	0.2927 (11)	0.7365 (8)	0.046 (3)*	0.25
C21'	0.4481 (4)	−0.0029 (9)	0.7343 (5)	0.062 (2)*	0.50
H21D	0.4780 (4)	−0.1093 (9)	0.7281 (5)	0.093*	0.50
H21E	0.4189 (4)	0.0174 (9)	0.6801 (5)	0.093*	0.50
H21F	0.4128 (4)	−0.0144 (9)	0.7840 (5)	0.093*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0180 (3)	0.0195 (3)	0.0356 (3)	0.0028 (2)	0.0004 (2)	−0.0003 (2)
O1	0.0191 (8)	0.0290 (8)	0.0544 (10)	0.0058 (7)	0.0052 (8)	−0.0013 (8)
O2	0.0242 (8)	0.0228 (8)	0.0467 (10)	−0.0009 (7)	0.0012 (7)	−0.0054 (7)
N1	0.0142 (9)	0.0215 (9)	0.0314 (10)	−0.0006 (8)	0.0015 (8)	0.0038 (8)
C1	0.0154 (10)	0.0226 (10)	0.0222 (10)	0.0023 (8)	−0.0003 (8)	0.0028 (8)
C2	0.0145 (10)	0.0228 (11)	0.0399 (13)	−0.0030 (8)	0.0008 (9)	0.0028 (10)
C3	0.0211 (11)	0.0186 (10)	0.0441 (14)	−0.0011 (9)	−0.0010 (10)	−0.0006 (10)
C10	0.0355 (13)	0.0230 (11)	0.0345 (13)	0.0035 (10)	−0.0060 (11)	0.0065 (10)
C11	0.0404 (15)	0.0383 (14)	0.0424 (15)	0.0006 (12)	−0.0027 (12)	0.0119 (12)
C12	0.069 (2)	0.055 (2)	0.044 (2)	0.001 (2)	−0.001 (2)	0.018 (2)
C13	0.102 (3)	0.052 (2)	0.036 (2)	0.001 (2)	−0.020 (2)	0.0156 (14)
C14	0.087 (3)	0.046 (2)	0.051 (2)	−0.011 (2)	−0.030 (2)	0.008 (2)
C15	0.051 (2)	0.0332 (14)	0.051 (2)	−0.0082 (13)	−0.0154 (14)	0.0097 (13)
C20	0.047 (2)	0.024 (2)	0.042 (2)	0.000	−0.002 (2)	0.000

Geometric parameters (Å, º)

S1—O2	1.421 (2)	C13—C14	1.365 (5)
S1—O1	1.432 (2)	C14—C15	1.383 (4)
S1—N1	1.631 (2)	C20—O3'^ii	1.225 (9)
S1—C10	1.754 (3)	C20—O3'	1.225 (9)
N1—C1	1.427 (3)	C20—O3	1.246 (9)
C1—C2	1.379 (3)	C20—O3^ii	1.246 (9)
C1—C3	1.382 (3)	C20—C21	1.474 (6)
C2—C3^i	1.378 (3)	C20—C21^ii	1.474 (6)
C3—C2^i	1.378 (3)	C20—C21'	1.475 (7)
C10—C15	1.380 (4)	C20—C21'^ii	1.475 (7)
C10—C11	1.383 (4)	O3—O3^ii	1.08 (2)
C11—C12	1.377 (4)	O3—C21^ii	1.831 (13)
C12—C13	1.373 (5)	O3'—O3'^ii	0.85 (2)
O2—S1—O1	119.30 (10)	C13—C14—C15	120.2 (3)
O2—S1—N1	108.87 (10)	C10—C15—C14	118.7 (3)
O1—S1—N1	104.44 (10)	O3'^ii—C20—O3'	40.7 (9)
O2—S1—C10	108.05 (11)	O3—C20—O3^ii	51.4 (10)
O1—S1—C10	108.06 (11)	O3—C20—C21	119.8 (7)
N1—S1—C10	107.59 (11)	O3^ii—C20—C21	84.2 (6)
C1—N1—S1	123.8 (2)	O3—C20—C21^ii	84.2 (6)
C2—C1—C3	119.0 (2)	O3^ii—C20—C21^ii	119.8 (7)
C2—C1—N1	118.2 (2)	C21—C20—C21^ii	154.7 (6)
C3—C1—N1	122.7 (2)	O3'^ii—C20—C21'	159.7 (7)
C3^i—C2—C1	121.0 (2)	O3'—C20—C21'	120.5 (6)
C2^i—C3—C1	120.0 (2)	O3'^ii—C20—C21'^ii	120.5 (6)
C15—C10—C11	121.2 (3)	O3'—C20—C21'^ii	159.7 (7)
C15—C10—S1	118.9 (2)	C21'—C20—C21'^ii	79.1 (6)
C11—C10—S1	119.9 (2)	O3^ii—O3—C20	64.3 (5)
C12—C11—C10	119.0 (3)	O3^ii—O3—C21^ii	105.1 (9)
C13—C12—C11	120.0 (3)	C20—O3—C21^ii	53.2 (4)
C14—C13—C12	120.9 (3)	O3'^ii—O3'—C20	69.6 (5)
O2—S1—N1—C1	56.0 (2)	C13—C14—C15—C10	0.6 (5)
O1—S1—N1—C1	−175.5 (2)	O3'^ii—C20—O3—O3^ii	−50.0 (18)
C10—S1—N1—C1	−60.8 (2)	O3'—C20—O3—O3^ii	28.8 (9)
S1—N1—C1—C2	142.8 (2)	O3^ii—C20—O3—O3^ii	0.000 (3)
S1—N1—C1—C3	−40.0 (3)	C21—C20—O3—O3^ii	52.6 (15)
C3—C1—C2—C3^i	0.2 (4)	C21^ii—C20—O3—O3^ii	−136.1 (13)
N1—C1—C2—C3^i	177.6 (2)	C21'—C20—O3—O3^ii	83.6 (17)
C2—C1—C3—C2^i	−0.2 (4)	C21'^ii—C20—O3—O3^ii	−146.9 (10)
N1—C1—C3—C2^i	−177.4 (2)	O3'^ii—C20—O3—C21^ii	86 (3)
O2—S1—C10—C15	165.7 (2)	O3'—C20—O3—C21^ii	164.9 (14)
O1—S1—C10—C15	35.3 (2)	O3^ii—C20—O3—C21^ii	136.1 (13)
N1—S1—C10—C15	−76.9 (2)	C21—C20—O3—C21^ii	−171.3 (3)
O2—S1—C10—C11	−13.2 (2)	C21^ii—C20—O3—C21^ii	0.0
O1—S1—C10—C11	−143.5 (2)	C21'—C20—O3—C21^ii	−140.3 (12)
N1—S1—C10—C11	104.2 (2)	C21'^ii—C20—O3—C21^ii	−10.8 (6)
C15—C10—C11—C12	0.4 (4)	O3'^ii—C20—O3'—O3'^ii	0.000 (4)
S1—C10—C11—C12	179.2 (2)	O3—C20—O3'—O3'^ii	−36.9 (11)
C10—C11—C12—C13	−0.5 (5)	O3^ii—C20—O3'—O3'^ii	73 (2)
C11—C12—C13—C14	0.6 (5)	C21—C20—O3'—O3'^ii	163.8 (19)
C12—C13—C14—C15	−0.7 (5)	C21^ii—C20—O3'—O3'^ii	−19 (2)
C11—C10—C15—C14	−0.5 (4)	C21'—C20—O3'—O3'^ii	169.7 (15)
S1—C10—C15—C14	−179.3 (2)	C21'^ii—C20—O3'—O3'^ii	−26 (4)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, y, −z+3/2.

(bock510)

Crystal data

C18H16N2O4S2·2[SO(CH3)2]	Z = 2
Mr = 544.70	F(000) = 572
Triclinic, P1	Dx = 1.383 Mg m^−3
a = 8.4277 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.0779 (14) Å	Cell parameters from 94 reflections
c = 13.401 (2) Å	θ = 8.5–21°
α = 116.532 (6)°	µ = 0.40 mm^−1
β = 97.10 (2)°	T = 150 K
γ = 90.425 (15)°	Block, colourless
V = 1308.1 (3) Å^3	0.80 × 0.60 × 0.45 mm

Data collection

Siemens P4 four circle diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 29.0°, θmin = 2.8°
Graphite monochromator	h = 0→11
ω scan	k = −15→15
6714 measured reflections	l = −18→18
6312 independent reflections	4 standard reflections every 100 reflections
5457 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters not defined?
wR(F^2) = 0.146	Calculated w = 1/[σ^2(Fo^2) + (0.075P)^2 + 1.2556P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
6312 reflections	Δρmax = 0.76 e Å^−3
324 parameters	Δρmin = −0.50 e Å^−3
6 restraints	Extinction correction: SHELXL93, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (17)

Special details

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 on F² for ALL reflections except for 2 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	−0.09919 (6)	0.25445 (5)	−0.07086 (4)	0.02925 (14)
O1	−0.1965 (2)	0.17004 (16)	−0.16852 (15)	0.0404 (4)
O2	−0.1409 (2)	0.37065 (15)	−0.02263 (17)	0.0440 (4)
N1	−0.0961 (2)	0.21628 (16)	0.02952 (16)	0.0286 (4)
H1N	−0.057 (4)	0.268 (3)	0.088 (3)	0.056 (10)*
C1	−0.0483 (2)	0.10617 (17)	0.01288 (16)	0.0245 (4)
C2	0.0840 (2)	0.09869 (17)	0.08167 (16)	0.0269 (4)
H2	0.1416	0.1668	0.1381	0.032*
C3	−0.1328 (3)	0.00618 (18)	−0.06919 (17)	0.0278 (4)
H3	−0.2238	0.0102	−0.1165	0.033*
C10	0.0977 (3)	0.25045 (19)	−0.10287 (17)	0.0288 (4)
C11	0.1902 (3)	0.3513 (2)	−0.0675 (2)	0.0431 (6)
H11	0.1484	0.4232	−0.0264	0.052*
C12	0.3451 (4)	0.3454 (3)	−0.0930 (3)	0.0563 (8)
H12	0.4093	0.4141	−0.0708	0.068*
C13	0.4067 (3)	0.2417 (3)	−0.1498 (2)	0.0528 (8)
H13	0.5140	0.2390	−0.1652	0.063*
C14	0.3147 (3)	0.1415 (3)	−0.1846 (2)	0.0473 (6)
H14	0.3585	0.0699	−0.2237	0.057*
C15	0.1582 (3)	0.1451 (2)	−0.16259 (19)	0.0357 (5)
H15	0.0929	0.0762	−0.1881	0.043*
S3	0.03824 (11)	0.49728 (7)	0.30326 (7)	0.0458 (2)	0.80
S3'	0.1855 (5)	0.4674 (3)	0.2857 (3)	0.0517 (8)*	0.20
O5	0.0625 (3)	0.37340 (17)	0.23687 (18)	0.0681 (7)
C41	0.1669 (4)	0.5458 (3)	0.4299 (2)	0.0566 (8)
H41A	0.1071	0.5874	0.4928	0.085*
H41B	0.2534	0.5971	0.4312	0.085*
H41C	0.2127	0.4803	0.4370	0.085*
C42	0.1380 (6)	0.5716 (3)	0.2436 (3)	0.0775 (12)
H42A	0.0668	0.6256	0.2322	0.116*
H42B	0.1671	0.5167	0.1709	0.116*
H42C	0.2352	0.6138	0.2945	0.116*
S2	0.39871 (6)	−0.69356 (4)	0.54782 (4)	0.02850 (14)
O3	0.4117 (2)	−0.61185 (15)	0.50525 (16)	0.0412 (4)
O4	0.4423 (2)	−0.65901 (15)	0.66526 (13)	0.0387 (4)
N2	0.5100 (2)	−0.79607 (17)	0.47802 (17)	0.0289 (4)
H2N	0.504 (4)	−0.805 (3)	0.419 (3)	0.044 (9)*
C21	0.5034 (2)	−0.89900 (18)	0.48996 (16)	0.0245 (4)
C22	0.4272 (2)	−0.99911 (19)	0.40221 (16)	0.0267 (4)
H22	0.3771	−0.9982	0.3351	0.032*
C23	0.5762 (2)	−0.90057 (19)	0.58807 (17)	0.0277 (4)
H23	0.6282	−0.8324	0.6484	0.033*
C30	0.2023 (2)	−0.75723 (18)	0.50796 (18)	0.0277 (4)
C31	0.1203 (3)	−0.7749 (2)	0.40505 (19)	0.0364 (5)
H31	0.1658	−0.7478	0.3591	0.044*
C32	−0.0294 (3)	−0.8328 (3)	0.3706 (2)	0.0471 (7)
H32	−0.0875	−0.8459	0.3001	0.057*
C33	−0.0951 (3)	−0.8716 (2)	0.4373 (3)	0.0492 (7)
H33	−0.1983	−0.9112	0.4125	0.059*
C34	−0.0127 (3)	−0.8536 (2)	0.5397 (3)	0.0458 (6)
H34	−0.0587	−0.8810	0.5852	0.055*
C35	0.1371 (3)	−0.7956 (2)	0.5763 (2)	0.0365 (5)
H35	0.1945	−0.7821	0.6472	0.044*
S4	0.59352 (12)	−0.79142 (11)	0.20448 (9)	0.0571 (3)	0.80
S4'	0.4746 (3)	−0.7585 (2)	0.2199 (2)	0.0335 (5)*	0.20
O6	0.4925 (3)	−0.8476 (2)	0.25020 (18)	0.0669 (7)
C51	0.5116 (5)	−0.8239 (5)	0.0712 (3)	0.0918 (16)
H51A	0.5893	−0.8613	0.0196	0.138*
H51B	0.4153	−0.8757	0.0500	0.138*
H51C	0.4825	−0.7534	0.0668	0.138*
C52	0.5901 (12)	−0.6488 (5)	0.2729 (6)	0.219 (6)
H52A	0.6993	−0.6135	0.2898	0.328*
H52B	0.5229	−0.6218	0.2256	0.328*
H52C	0.5459	−0.6274	0.3433	0.328*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0309 (3)	0.0244 (3)	0.0349 (3)	0.00325 (19)	0.00115 (19)	0.0164 (2)
O1	0.0366 (9)	0.0429 (10)	0.0409 (9)	−0.0034 (7)	−0.0104 (7)	0.0224 (8)
O2	0.0506 (11)	0.0313 (9)	0.0582 (11)	0.0141 (8)	0.0130 (8)	0.0259 (8)
N1	0.0350 (9)	0.0209 (9)	0.0295 (9)	0.0005 (7)	0.0055 (7)	0.0108 (7)
C1	0.0293 (9)	0.0202 (9)	0.0246 (8)	−0.0023 (7)	0.0047 (7)	0.0104 (7)
C2	0.0307 (10)	0.0218 (9)	0.0251 (9)	−0.0067 (8)	−0.0003 (7)	0.0090 (7)
C3	0.0296 (10)	0.0249 (10)	0.0270 (9)	−0.0048 (8)	−0.0020 (7)	0.0117 (8)
C10	0.0318 (10)	0.0288 (11)	0.0278 (9)	−0.0006 (8)	0.0011 (7)	0.0152 (8)
C11	0.0482 (14)	0.0337 (13)	0.0433 (13)	−0.0075 (11)	0.0031 (11)	0.0148 (10)
C12	0.0509 (16)	0.065 (2)	0.0500 (16)	−0.0248 (15)	−0.0008 (12)	0.0253 (14)
C13	0.0356 (13)	0.089 (2)	0.0395 (13)	0.0000 (14)	0.0053 (10)	0.0342 (15)
C14	0.0476 (14)	0.0632 (18)	0.0359 (12)	0.0155 (13)	0.0154 (11)	0.0240 (12)
C15	0.0433 (12)	0.0348 (12)	0.0302 (10)	0.0036 (10)	0.0082 (9)	0.0149 (9)
S3	0.0463 (4)	0.0289 (4)	0.0500 (5)	−0.0002 (3)	−0.0060 (3)	0.0102 (3)
O5	0.117 (2)	0.0248 (10)	0.0448 (11)	−0.0067 (11)	−0.0217 (12)	0.0085 (8)
C41	0.079 (2)	0.0364 (14)	0.0421 (14)	−0.0007 (14)	−0.0005 (14)	0.0094 (11)
C42	0.139 (4)	0.0429 (18)	0.0563 (19)	0.003 (2)	0.015 (2)	0.0274 (15)
S2	0.0317 (3)	0.0230 (3)	0.0306 (3)	−0.00167 (19)	0.00175 (19)	0.01270 (19)
O3	0.0489 (10)	0.0288 (9)	0.0518 (10)	−0.0026 (7)	0.0057 (8)	0.0238 (8)
O4	0.0450 (9)	0.0338 (9)	0.0298 (8)	−0.0008 (7)	−0.0016 (7)	0.0095 (7)
N2	0.0297 (9)	0.0297 (9)	0.0320 (9)	0.0009 (7)	0.0068 (7)	0.0175 (7)
C21	0.0208 (8)	0.0271 (10)	0.0286 (9)	0.0011 (7)	0.0054 (7)	0.0146 (8)
C22	0.0257 (9)	0.0301 (10)	0.0246 (9)	0.0005 (8)	0.0015 (7)	0.0132 (8)
C23	0.0260 (9)	0.0281 (10)	0.0260 (9)	−0.0016 (8)	0.0010 (7)	0.0104 (8)
C30	0.0281 (9)	0.0223 (10)	0.0325 (10)	0.0035 (8)	0.0046 (7)	0.0120 (8)
C31	0.0356 (11)	0.0379 (13)	0.0325 (11)	0.0047 (9)	0.0023 (9)	0.0138 (9)
C32	0.0343 (12)	0.0493 (15)	0.0413 (13)	0.0064 (11)	−0.0032 (10)	0.0079 (11)
C33	0.0267 (11)	0.0426 (14)	0.0624 (17)	−0.0004 (10)	0.0101 (11)	0.0086 (12)
C34	0.0380 (13)	0.0416 (14)	0.0622 (17)	0.0026 (11)	0.0190 (12)	0.0245 (12)
C35	0.0369 (12)	0.0373 (13)	0.0408 (12)	0.0052 (10)	0.0101 (9)	0.0213 (10)
S4	0.0468 (5)	0.0857 (8)	0.0552 (5)	−0.0068 (5)	−0.0043 (4)	0.0493 (5)
O6	0.113 (2)	0.0544 (13)	0.0433 (11)	−0.0083 (13)	0.0178 (12)	0.0293 (10)
C51	0.084 (3)	0.150 (5)	0.053 (2)	−0.034 (3)	−0.0018 (18)	0.059 (3)
C52	0.477 (17)	0.059 (3)	0.110 (5)	−0.068 (6)	0.128 (8)	0.009 (3)

Geometric parameters (Å, º)

S1—O1	1.4265 (18)	S2—O4	1.4266 (17)
S1—O2	1.4273 (18)	S2—O3	1.4275 (18)
S1—N1	1.628 (2)	S2—N2	1.633 (2)
S1—C10	1.760 (2)	S2—C30	1.756 (2)
N1—C1	1.424 (3)	N2—C21	1.426 (3)
C1—C2	1.390 (3)	C21—C23	1.389 (3)
C1—C3	1.391 (3)	C21—C22	1.391 (3)
C2—C3^i	1.378 (3)	C22—C23^ii	1.376 (3)
C3—C2^i	1.378 (3)	C23—C22^ii	1.376 (3)
C10—C11	1.380 (3)	C30—C31	1.382 (3)
C10—C15	1.388 (3)	C30—C35	1.387 (3)
C11—C12	1.384 (4)	C31—C32	1.381 (4)
C12—C13	1.370 (5)	C32—C33	1.374 (4)
C13—C14	1.373 (5)	C33—C34	1.377 (4)
C14—C15	1.384 (4)	C34—C35	1.382 (4)
S3—S3'	1.321 (4)	S4—S4'	1.101 (3)
S3—O5	1.490 (2)	S4—O6	1.470 (2)
S3—C41	1.741 (3)	S4—C52	1.674 (6)
S3—C42	1.773 (4)	S4—C51	1.691 (4)
S3'—O5	1.452 (4)	S4'—O6	1.399 (4)
S3'—C42	1.726 (5)	S4'—C52	1.552 (7)
S3'—C41	1.765 (5)	S4'—C51	1.853 (5)
O1—S1—O2	119.85 (12)	O4—S2—O3	119.71 (11)
O1—S1—N1	108.10 (11)	O4—S2—N2	108.56 (11)
O2—S1—N1	105.29 (11)	O3—S2—N2	105.40 (11)
O1—S1—C10	107.29 (11)	O4—S2—C30	108.11 (11)
O2—S1—C10	108.64 (11)	O3—S2—C30	109.07 (11)
N1—S1—C10	107.04 (10)	N2—S2—C30	105.05 (10)
C1—N1—S1	120.60 (14)	C21—N2—S2	118.74 (14)
C2—C1—C3	119.32 (19)	C23—C21—C22	119.6 (2)
C2—C1—N1	119.15 (18)	C23—C21—N2	120.28 (19)
C3—C1—N1	121.52 (19)	C22—C21—N2	120.07 (18)
C3^i—C2—C1	120.92 (18)	C23^ii—C22—C21	120.44 (18)
C2^i—C3—C1	119.76 (19)	C22^ii—C23—C21	119.92 (19)
C11—C10—C15	121.0 (2)	C31—C30—C35	121.5 (2)
C11—C10—S1	119.95 (19)	C31—C30—S2	118.81 (18)
C15—C10—S1	119.07 (17)	C35—C30—S2	119.53 (17)
C10—C11—C12	118.7 (3)	C32—C31—C30	118.4 (2)
C13—C12—C11	120.7 (3)	C33—C32—C31	120.7 (3)
C12—C13—C14	120.6 (3)	C32—C33—C34	120.5 (2)
C13—C14—C15	119.9 (3)	C33—C34—C35	119.9 (3)
C14—C15—C10	119.2 (2)	C34—C35—C30	118.9 (2)
S3'—S3—O5	61.85 (19)	S4'—S4—O6	64.04 (19)
S3'—S3—C41	68.82 (19)	S4'—S4—C52	64.2 (3)
O5—S3—C41	106.74 (14)	O6—S4—C52	111.0 (2)
S3'—S3—C42	66.0 (2)	S4'—S4—C51	80.1 (2)
O5—S3—C42	106.79 (17)	O6—S4—C51	108.91 (18)
C41—S3—C42	97.81 (19)	C52—S4—C51	103.6 (4)
S3—S3'—O5	64.8 (2)	S4—S4'—O6	70.9 (2)
S3—S3'—C42	69.7 (2)	S4—S4'—C52	76.1 (3)
O5—S3'—C42	111.0 (3)	O6—S4'—C52	123.0 (4)
S3—S3'—C41	66.90 (19)	S4—S4'—C51	64.1 (2)
O5—S3'—C41	107.3 (3)	O6—S4'—C51	103.9 (3)
C42—S3'—C41	98.7 (2)	C52—S4'—C51	101.6 (3)
S3'—O5—S3	53.36 (17)	S4'—O6—S4	45.03 (14)
S3—C41—S3'	44.28 (15)	S4—C51—S4'	35.82 (12)
S3'—C42—S3	44.36 (15)	S4'—C52—S4	39.67 (17)
O1—S1—N1—C1	54.80 (19)	O4—S2—N2—C21	59.60 (19)
O2—S1—N1—C1	−175.99 (17)	O3—S2—N2—C21	−171.00 (16)
C10—S1—N1—C1	−60.49 (19)	C30—S2—N2—C21	−55.85 (18)
S1—N1—C1—C2	119.49 (19)	S2—N2—C21—C23	−74.0 (2)
S1—N1—C1—C3	−61.7 (2)	S2—N2—C21—C22	107.5 (2)
C3—C1—C2—C3^i	0.3 (3)	C23—C21—C22—C23^ii	−0.1 (3)
N1—C1—C2—C3^i	179.20 (19)	N2—C21—C22—C23^ii	178.34 (19)
C2—C1—C3—C2^i	−0.3 (3)	C22—C21—C23—C22^ii	0.1 (3)
N1—C1—C3—C2^i	−179.17 (19)	N2—C21—C23—C22^ii	−178.34 (18)
O1—S1—C10—C11	139.1 (2)	O4—S2—C30—C31	165.92 (18)
O2—S1—C10—C11	8.1 (2)	O3—S2—C30—C31	34.3 (2)
N1—S1—C10—C11	−105.1 (2)	N2—S2—C30—C31	−78.3 (2)
O1—S1—C10—C15	−41.7 (2)	O4—S2—C30—C35	−18.4 (2)
O2—S1—C10—C15	−172.63 (18)	O3—S2—C30—C35	−150.09 (19)
N1—S1—C10—C15	74.13 (19)	N2—S2—C30—C35	97.34 (19)
C15—C10—C11—C12	0.2 (4)	C35—C30—C31—C32	−0.4 (4)
S1—C10—C11—C12	179.4 (2)	S2—C30—C31—C32	175.17 (19)
C10—C11—C12—C13	−1.6 (4)	C30—C31—C32—C33	0.1 (4)
C11—C12—C13—C14	1.4 (4)	C31—C32—C33—C34	−0.1 (4)
C12—C13—C14—C15	0.2 (4)	C32—C33—C34—C35	0.3 (4)
C13—C14—C15—C10	−1.6 (4)	C33—C34—C35—C30	−0.6 (4)
C11—C10—C15—C14	1.4 (4)	C31—C30—C35—C34	0.6 (4)
S1—C10—C15—C14	−177.82 (18)	S2—C30—C35—C34	−174.92 (19)
C41—S3—S3'—O5	123.9 (2)	C52—S4—S4'—O6	−132.7 (3)
C42—S3—S3'—O5	−126.7 (2)	C51—S4—S4'—O6	116.8 (2)
O5—S3—S3'—C42	126.7 (2)	O6—S4—S4'—C52	132.7 (3)
C41—S3—S3'—C42	−109.4 (2)	C51—S4—S4'—C52	−110.5 (3)
O5—S3—S3'—C41	−123.9 (2)	O6—S4—S4'—C51	−116.8 (2)
C42—S3—S3'—C41	109.4 (2)	C52—S4—S4'—C51	110.5 (3)
C42—S3'—O5—S3	−53.7 (2)	C52—S4'—O6—S4	−58.2 (3)
C41—S3'—O5—S3	53.1 (2)	C51—S4'—O6—S4	55.78 (19)
C41—S3—O5—S3'	−53.9 (2)	C52—S4—O6—S4'	45.1 (4)
C42—S3—O5—S3'	49.9 (2)	C51—S4—O6—S4'	−68.4 (3)
O5—S3—C41—S3'	49.8 (2)	O6—S4—C51—S4'	58.0 (2)
C42—S3—C41—S3'	−60.4 (2)	C52—S4—C51—S4'	−60.2 (3)
O5—S3'—C41—S3	−51.9 (2)	O6—S4'—C51—S4	−60.4 (2)
C42—S3'—C41—S3	63.5 (2)	C52—S4'—C51—S4	68.2 (4)
O5—S3'—C42—S3	51.0 (2)	O6—S4'—C52—S4	55.8 (3)
C41—S3'—C42—S3	−61.34 (19)	C51—S4'—C52—S4	−59.3 (2)
O5—S3—C42—S3'	−47.6 (2)	O6—S4—C52—S4'	−45.0 (3)
C41—S3—C42—S3'	62.6 (2)	C51—S4—C52—S4'	71.7 (2)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y−2, −z+1.