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.
Supporting information
CCDC references: 144354; 144355; 144356; 144357
For all compounds, program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993).
Crystal data top
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) Å3 | 0.65 × 0.50 × 0.45 mm |
Z = 2 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters not defined? |
wR(F2) = 0.107 | Calculated w = 1/[σ2(Fo2) + (0.053P)2 + 0.4032P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0076 (25) |
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 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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
S1—O2 | 1.4218 (11) | C3—C2i | 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—C3i | 1.386 (2) | | |
| | | |
O2—S1—O1 | 119.18 (7) | C3i—C2—C1 | 119.43 (13) |
O2—S1—N1 | 108.29 (7) | C2i—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—C3i | −0.2 (2) | C10—C11—C12—C13 | −0.8 (3) |
N1—C1—C2—C3i | −176.44 (14) | C11—C12—C13—C14 | −0.3 (4) |
C2—C1—C3—C2i | 0.2 (2) | C12—C13—C14—C15 | 0.8 (3) |
N1—C1—C3—C2i | 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. |
Crystal data top
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) Å3 | 0.60 × 0.50 × 0.40 mm |
Z = 2 | |
Data collection top
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 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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-atom parameters not defined? |
S = 1.03 | Calculated w = 1/[σ2(Fo2) + (0.046P)2 + 0.4377P] where P = (Fo2 + 2Fc2)/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 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 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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
S1—O2 | 1.4303 (11) | C3—C2i | 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—C3i | 1.390 (2) | | |
| | | |
O2—S1—O1 | 119.92 (7) | C1—C2—C3i | 120.12 (13) |
O2—S1—N1 | 107.95 (7) | C2i—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—C3i | 0.1 (2) | C10—C11—C12—C13 | 0.0 (3) |
N1—C1—C2—C3i | −179.16 (13) | C11—C12—C13—C14 | −0.1 (3) |
C2—C1—C3—C2i | −0.1 (2) | C12—C13—C14—C15 | 0.0 (3) |
N1—C1—C3—C2i | 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. |
Crystal data top
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) Å3 | Block, colourless |
Z = 4 | 0.70 × 0.65 × 0.40 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters not defined? |
wR(F2) = 0.114 | Calculated w = 1/[σ2(Fo2) + (0.0446P)2 + 2.2606P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0071 (7) |
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 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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—O3ii | 1.246 (9) |
C1—C3 | 1.382 (3) | C20—C21 | 1.474 (6) |
C2—C3i | 1.378 (3) | C20—C21ii | 1.474 (6) |
C3—C2i | 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—O3ii | 1.08 (2) |
C11—C12 | 1.377 (4) | O3—C21ii | 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—O3ii | 51.4 (10) |
O1—S1—C10 | 108.06 (11) | O3—C20—C21 | 119.8 (7) |
N1—S1—C10 | 107.59 (11) | O3ii—C20—C21 | 84.2 (6) |
C1—N1—S1 | 123.8 (2) | O3—C20—C21ii | 84.2 (6) |
C2—C1—C3 | 119.0 (2) | O3ii—C20—C21ii | 119.8 (7) |
C2—C1—N1 | 118.2 (2) | C21—C20—C21ii | 154.7 (6) |
C3—C1—N1 | 122.7 (2) | O3'ii—C20—C21' | 159.7 (7) |
C3i—C2—C1 | 121.0 (2) | O3'—C20—C21' | 120.5 (6) |
C2i—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) | O3ii—O3—C20 | 64.3 (5) |
C12—C11—C10 | 119.0 (3) | O3ii—O3—C21ii | 105.1 (9) |
C13—C12—C11 | 120.0 (3) | C20—O3—C21ii | 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—O3ii | −50.0 (18) |
C10—S1—N1—C1 | −60.8 (2) | O3'—C20—O3—O3ii | 28.8 (9) |
S1—N1—C1—C2 | 142.8 (2) | O3ii—C20—O3—O3ii | 0.000 (3) |
S1—N1—C1—C3 | −40.0 (3) | C21—C20—O3—O3ii | 52.6 (15) |
C3—C1—C2—C3i | 0.2 (4) | C21ii—C20—O3—O3ii | −136.1 (13) |
N1—C1—C2—C3i | 177.6 (2) | C21'—C20—O3—O3ii | 83.6 (17) |
C2—C1—C3—C2i | −0.2 (4) | C21'ii—C20—O3—O3ii | −146.9 (10) |
N1—C1—C3—C2i | −177.4 (2) | O3'ii—C20—O3—C21ii | 86 (3) |
O2—S1—C10—C15 | 165.7 (2) | O3'—C20—O3—C21ii | 164.9 (14) |
O1—S1—C10—C15 | 35.3 (2) | O3ii—C20—O3—C21ii | 136.1 (13) |
N1—S1—C10—C15 | −76.9 (2) | C21—C20—O3—C21ii | −171.3 (3) |
O2—S1—C10—C11 | −13.2 (2) | C21ii—C20—O3—C21ii | 0.0 |
O1—S1—C10—C11 | −143.5 (2) | C21'—C20—O3—C21ii | −140.3 (12) |
N1—S1—C10—C11 | 104.2 (2) | C21'ii—C20—O3—C21ii | −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) | O3ii—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) | C21ii—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. |
Crystal data top
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) Å3 | 0.80 × 0.60 × 0.45 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters not defined? |
wR(F2) = 0.146 | Calculated w = 1/[σ2(Fo2) + (0.075P)2 + 1.2556P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0070 (17) |
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 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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C3i | 1.378 (3) | C22—C23ii | 1.376 (3) |
C3—C2i | 1.378 (3) | C23—C22ii | 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) |
C3i—C2—C1 | 120.92 (18) | C23ii—C22—C21 | 120.44 (18) |
C2i—C3—C1 | 119.76 (19) | C22ii—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—C3i | 0.3 (3) | C23—C21—C22—C23ii | −0.1 (3) |
N1—C1—C2—C3i | 179.20 (19) | N2—C21—C22—C23ii | 178.34 (19) |
C2—C1—C3—C2i | −0.3 (3) | C22—C21—C23—C22ii | 0.1 (3) |
N1—C1—C3—C2i | −179.17 (19) | N2—C21—C23—C22ii | −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. |