Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015703/ci6396sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015703/ci6396Isup2.hkl |
CCDC reference: 248763
Data collection: SMART (Bruker, 1997-1999); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1997-1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C16H11N2S2+·ClO4− | Z = 4 |
Mr = 394.84 | F(000) = 808 |
Triclinic, P1 | Dx = 1.611 Mg m−3 |
Hall symbol: -P 1 | Melting point: not measured K |
a = 10.435 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.199 (2) Å | Cell parameters from 13920 reflections |
c = 15.228 (3) Å | θ = 2.4–28.3° |
α = 86.001 (3)° | µ = 0.52 mm−1 |
β = 73.202 (3)° | T = 100 K |
γ = 72.859 (3)° | Prism, brown |
V = 1627.7 (5) Å3 | 0.44 × 0.39 × 0.14 mm |
Bruker SMART APEX diffractometer | 7974 independent reflections |
Radiation source: sealed tube | 7341 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 28.3°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −13→13 |
Tmin = 0.809, Tmax = 0.933 | k = −14→14 |
16611 measured reflections | l = −20→20 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0637P)2 + 1.8804P] where P = (Fo2 + 2Fc2)/3 |
7973 reflections | (Δ/σ)max = 0.001 |
459 parameters | Δρmax = 0.81 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Experimental. H1 and H19 were found in initial difference maps and refined isotropically. Remaining hydrogen atoms were included in calculated positions with a C—H distance of 0.95 Å and were included in the refinement in riding motion approximation with Uiso = 1.2Ueq of the carrier atom. |
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 | ||
N1 | 0.3818 (2) | 0.8392 (2) | 0.63029 (14) | 0.0190 (4) | |
C1 | 0.4031 (2) | 0.8571 (2) | 0.54117 (16) | 0.0167 (4) | |
C2 | 0.2989 (2) | 0.9411 (2) | 0.50483 (16) | 0.0161 (4) | |
N2 | 0.1791 (2) | 0.99865 (19) | 0.56490 (14) | 0.0160 (4) | |
C3 | 0.1513 (3) | 0.9834 (2) | 0.65796 (16) | 0.0170 (5) | |
C4 | 0.0218 (3) | 1.0453 (2) | 0.71797 (17) | 0.0209 (5) | |
H4 | −0.0511 | 1.0982 | 0.6955 | 0.025* | |
C5 | 0.0037 (3) | 1.0267 (3) | 0.81047 (18) | 0.0236 (5) | |
H5 | −0.0832 | 1.0670 | 0.8528 | 0.028* | |
C6 | 0.1123 (3) | 0.9490 (3) | 0.84319 (17) | 0.0231 (5) | |
H6 | 0.0980 | 0.9393 | 0.9075 | 0.028* | |
C7 | 0.2378 (3) | 0.8870 (2) | 0.78475 (17) | 0.0213 (5) | |
H7 | 0.3101 | 0.8346 | 0.8080 | 0.026* | |
C8 | 0.2585 (3) | 0.9020 (2) | 0.68918 (17) | 0.0181 (5) | |
C9 | 0.5411 (3) | 0.7888 (2) | 0.48366 (16) | 0.0172 (5) | |
C10 | 0.6259 (3) | 0.8240 (2) | 0.40525 (17) | 0.0201 (5) | |
H10 | 0.5975 | 0.8984 | 0.3732 | 0.024* | |
C11 | 0.7599 (3) | 0.7370 (3) | 0.37786 (18) | 0.0226 (5) | |
H11 | 0.8319 | 0.7473 | 0.3257 | 0.027* | |
C12 | 0.7752 (3) | 0.6370 (3) | 0.43382 (19) | 0.0237 (5) | |
H12 | 0.8580 | 0.5690 | 0.4248 | 0.028* | |
S1 | 0.62760 (7) | 0.64819 (6) | 0.52234 (4) | 0.02251 (15) | |
C13 | 0.3131 (3) | 0.9762 (2) | 0.40951 (16) | 0.0183 (5) | |
C14 | 0.2952 (3) | 1.0982 (2) | 0.37840 (17) | 0.0224 (5) | |
H14 | 0.2695 | 1.1694 | 0.4171 | 0.027* | |
C15 | 0.3202 (3) | 1.1030 (3) | 0.2824 (2) | 0.0329 (7) | |
H15 | 0.3159 | 1.1781 | 0.2488 | 0.039* | |
C16 | 0.3508 (3) | 0.9894 (3) | 0.24293 (18) | 0.0277 (6) | |
H16 | 0.3685 | 0.9766 | 0.1790 | 0.033* | |
S2 | 0.35405 (7) | 0.87209 (6) | 0.32061 (4) | 0.02371 (15) | |
Cl1 | 0.90574 (6) | 0.26979 (6) | 0.47879 (4) | 0.01971 (14) | |
O1 | 0.9486 (3) | 0.2278 (2) | 0.38545 (14) | 0.0400 (6) | |
O2 | 0.7576 (2) | 0.3208 (2) | 0.50820 (18) | 0.0421 (6) | |
O3 | 0.9450 (2) | 0.1626 (2) | 0.53456 (15) | 0.0337 (5) | |
O4 | 0.9734 (3) | 0.3597 (2) | 0.48688 (16) | 0.0372 (5) | |
N3 | 0.9071 (2) | 0.3537 (2) | 0.10358 (15) | 0.0199 (4) | |
C17 | 0.9271 (3) | 0.3674 (2) | 0.01425 (17) | 0.0174 (5) | |
C18 | 0.8199 (3) | 0.4472 (2) | −0.02174 (16) | 0.0176 (5) | |
N4 | 0.7011 (2) | 0.5071 (2) | 0.03771 (14) | 0.0178 (4) | |
C19 | 0.6752 (3) | 0.4946 (2) | 0.13053 (17) | 0.0185 (5) | |
C20 | 0.5453 (3) | 0.5557 (3) | 0.19107 (18) | 0.0229 (5) | |
H20 | 0.4718 | 0.6075 | 0.1687 | 0.027* | |
C21 | 0.5279 (3) | 0.5383 (3) | 0.28313 (18) | 0.0244 (5) | |
H21 | 0.4406 | 0.5778 | 0.3253 | 0.029* | |
C22 | 0.6376 (3) | 0.4626 (2) | 0.31621 (17) | 0.0225 (5) | |
H22 | 0.6237 | 0.4537 | 0.3805 | 0.027* | |
C23 | 0.7633 (3) | 0.4019 (2) | 0.25768 (17) | 0.0220 (5) | |
H23 | 0.8362 | 0.3508 | 0.2809 | 0.026* | |
C24 | 0.7838 (3) | 0.4158 (2) | 0.16230 (17) | 0.0176 (5) | |
C25 | 1.0630 (3) | 0.2965 (2) | −0.04288 (17) | 0.0187 (5) | |
C26 | 1.1375 (3) | 0.3103 (2) | −0.13167 (18) | 0.0214 (5) | |
H26 | 1.1032 | 0.3729 | −0.1714 | 0.026* | |
C27 | 1.2704 (3) | 0.2218 (3) | −0.15758 (19) | 0.0254 (5) | |
H27 | 1.3353 | 0.2188 | −0.2164 | 0.031* | |
C28 | 1.2958 (3) | 0.1414 (3) | −0.08971 (19) | 0.0259 (6) | |
H28 | 1.3796 | 0.0753 | −0.0957 | 0.031* | |
S3 | 1.15926 (7) | 0.17294 (7) | 0.00756 (5) | 0.02582 (16) | |
C29 | 0.8312 (3) | 0.4678 (2) | −0.11970 (17) | 0.0192 (5) | |
C30 | 0.8447 (3) | 0.5748 (3) | −0.16891 (19) | 0.0252 (5) | |
H30 | 0.8424 | 0.6500 | −0.1424 | 0.030* | |
C31 | 0.8620 (3) | 0.5581 (3) | −0.2630 (2) | 0.0344 (7) | |
H31 | 0.8756 | 0.6205 | −0.3074 | 0.041* | |
C32 | 0.8574 (3) | 0.4453 (3) | −0.28339 (19) | 0.0314 (6) | |
H32 | 0.8656 | 0.4198 | −0.3434 | 0.038* | |
S4 | 0.83539 (8) | 0.35278 (7) | −0.18999 (5) | 0.02680 (16) | |
Cl2 | 0.59238 (6) | 0.22853 (6) | 0.01024 (4) | 0.02061 (14) | |
O5 | 0.5887 (3) | 0.1883 (2) | −0.07619 (17) | 0.0435 (6) | |
O6 | 0.5234 (2) | 0.1641 (2) | 0.08320 (17) | 0.0421 (6) | |
O7 | 0.5221 (2) | 0.36182 (19) | 0.02118 (16) | 0.0314 (5) | |
O8 | 0.7348 (2) | 0.20932 (19) | 0.00995 (14) | 0.0284 (4) | |
H19 | 0.634 (4) | 0.557 (3) | 0.018 (2) | 0.027 (8)* | |
H1 | 0.114 (4) | 1.049 (3) | 0.546 (2) | 0.027 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0210 (10) | 0.0197 (10) | 0.0149 (10) | −0.0040 (8) | −0.0052 (8) | 0.0011 (8) |
C1 | 0.0180 (11) | 0.0166 (11) | 0.0150 (11) | −0.0046 (9) | −0.0045 (9) | 0.0010 (8) |
C2 | 0.0189 (11) | 0.0158 (11) | 0.0131 (10) | −0.0052 (9) | −0.0040 (9) | 0.0020 (8) |
N2 | 0.0167 (9) | 0.0186 (10) | 0.0127 (9) | −0.0049 (8) | −0.0048 (7) | 0.0027 (7) |
C3 | 0.0206 (11) | 0.0173 (11) | 0.0132 (11) | −0.0070 (9) | −0.0038 (9) | 0.0019 (8) |
C4 | 0.0188 (11) | 0.0234 (12) | 0.0166 (11) | −0.0031 (10) | −0.0025 (9) | 0.0028 (9) |
C5 | 0.0252 (13) | 0.0244 (13) | 0.0157 (12) | −0.0048 (10) | −0.0003 (10) | 0.0016 (9) |
C6 | 0.0285 (13) | 0.0252 (13) | 0.0141 (11) | −0.0078 (11) | −0.0039 (10) | 0.0018 (9) |
C7 | 0.0255 (12) | 0.0246 (13) | 0.0144 (11) | −0.0074 (10) | −0.0072 (10) | 0.0042 (9) |
C8 | 0.0213 (11) | 0.0180 (11) | 0.0152 (11) | −0.0064 (9) | −0.0054 (9) | 0.0022 (9) |
C9 | 0.0170 (11) | 0.0185 (11) | 0.0156 (11) | −0.0038 (9) | −0.0056 (9) | 0.0015 (9) |
C10 | 0.0199 (12) | 0.0232 (12) | 0.0174 (11) | −0.0079 (10) | −0.0043 (9) | 0.0013 (9) |
C11 | 0.0180 (11) | 0.0275 (13) | 0.0223 (12) | −0.0084 (10) | −0.0029 (10) | −0.0022 (10) |
C12 | 0.0174 (11) | 0.0241 (13) | 0.0261 (13) | −0.0019 (10) | −0.0040 (10) | −0.0035 (10) |
S1 | 0.0200 (3) | 0.0214 (3) | 0.0217 (3) | −0.0013 (2) | −0.0045 (2) | 0.0033 (2) |
C13 | 0.0175 (11) | 0.0232 (12) | 0.0117 (10) | −0.0037 (9) | −0.0024 (8) | −0.0004 (9) |
C14 | 0.0261 (13) | 0.0241 (13) | 0.0139 (11) | −0.0043 (10) | −0.0041 (9) | 0.0012 (9) |
C15 | 0.0416 (17) | 0.0323 (15) | 0.0214 (14) | −0.0074 (13) | −0.0091 (12) | 0.0096 (11) |
C16 | 0.0247 (13) | 0.0441 (17) | 0.0116 (11) | −0.0085 (12) | −0.0031 (10) | 0.0034 (11) |
S2 | 0.0249 (3) | 0.0281 (3) | 0.0156 (3) | −0.0059 (3) | −0.0029 (2) | −0.0022 (2) |
Cl1 | 0.0210 (3) | 0.0208 (3) | 0.0194 (3) | −0.0065 (2) | −0.0093 (2) | 0.0050 (2) |
O1 | 0.0663 (16) | 0.0408 (13) | 0.0188 (10) | −0.0197 (12) | −0.0169 (10) | 0.0018 (9) |
O2 | 0.0213 (10) | 0.0402 (13) | 0.0568 (15) | −0.0012 (9) | −0.0105 (10) | 0.0176 (11) |
O3 | 0.0226 (10) | 0.0393 (12) | 0.0322 (11) | −0.0036 (9) | −0.0071 (8) | 0.0215 (9) |
O4 | 0.0457 (13) | 0.0403 (12) | 0.0360 (12) | −0.0245 (11) | −0.0152 (10) | 0.0025 (10) |
N3 | 0.0196 (10) | 0.0224 (11) | 0.0171 (10) | −0.0054 (8) | −0.0053 (8) | 0.0014 (8) |
C17 | 0.0171 (11) | 0.0179 (11) | 0.0178 (11) | −0.0053 (9) | −0.0056 (9) | 0.0014 (9) |
C18 | 0.0191 (11) | 0.0192 (11) | 0.0151 (11) | −0.0068 (9) | −0.0047 (9) | 0.0018 (9) |
N4 | 0.0187 (10) | 0.0189 (10) | 0.0145 (10) | −0.0040 (8) | −0.0044 (8) | 0.0021 (8) |
C19 | 0.0215 (12) | 0.0196 (11) | 0.0145 (11) | −0.0058 (9) | −0.0052 (9) | 0.0000 (9) |
C20 | 0.0204 (12) | 0.0254 (13) | 0.0176 (12) | −0.0017 (10) | −0.0025 (9) | 0.0021 (10) |
C21 | 0.0243 (13) | 0.0261 (13) | 0.0180 (12) | −0.0046 (10) | −0.0013 (10) | −0.0012 (10) |
C22 | 0.0287 (13) | 0.0258 (13) | 0.0145 (11) | −0.0101 (11) | −0.0065 (10) | 0.0027 (9) |
C23 | 0.0257 (13) | 0.0245 (13) | 0.0173 (12) | −0.0070 (10) | −0.0095 (10) | 0.0031 (9) |
C24 | 0.0182 (11) | 0.0182 (11) | 0.0165 (11) | −0.0055 (9) | −0.0050 (9) | 0.0016 (9) |
C25 | 0.0160 (11) | 0.0215 (12) | 0.0176 (11) | −0.0045 (9) | −0.0044 (9) | 0.0015 (9) |
C26 | 0.0197 (12) | 0.0228 (12) | 0.0212 (12) | −0.0072 (10) | −0.0041 (10) | 0.0026 (9) |
C27 | 0.0199 (12) | 0.0287 (14) | 0.0250 (13) | −0.0083 (11) | −0.0003 (10) | −0.0021 (10) |
C28 | 0.0184 (12) | 0.0261 (13) | 0.0281 (14) | −0.0028 (10) | −0.0020 (10) | −0.0023 (11) |
S3 | 0.0194 (3) | 0.0290 (4) | 0.0217 (3) | 0.0004 (3) | −0.0032 (2) | 0.0045 (3) |
C29 | 0.0180 (11) | 0.0227 (12) | 0.0158 (11) | −0.0043 (9) | −0.0047 (9) | −0.0006 (9) |
C30 | 0.0289 (13) | 0.0239 (13) | 0.0221 (13) | −0.0075 (11) | −0.0063 (11) | −0.0003 (10) |
C31 | 0.0369 (16) | 0.0392 (17) | 0.0223 (14) | −0.0081 (13) | −0.0069 (12) | 0.0123 (12) |
C32 | 0.0284 (14) | 0.0466 (18) | 0.0139 (12) | −0.0049 (13) | −0.0039 (10) | 0.0016 (11) |
S4 | 0.0326 (4) | 0.0305 (4) | 0.0167 (3) | −0.0095 (3) | −0.0053 (3) | −0.0013 (2) |
Cl2 | 0.0226 (3) | 0.0209 (3) | 0.0199 (3) | −0.0071 (2) | −0.0086 (2) | 0.0051 (2) |
O5 | 0.0558 (15) | 0.0495 (14) | 0.0343 (13) | −0.0203 (12) | −0.0198 (11) | −0.0063 (11) |
O6 | 0.0350 (12) | 0.0428 (13) | 0.0424 (13) | −0.0143 (10) | −0.0030 (10) | 0.0210 (11) |
O7 | 0.0291 (10) | 0.0233 (10) | 0.0456 (13) | −0.0034 (8) | −0.0206 (10) | 0.0024 (9) |
O8 | 0.0227 (10) | 0.0314 (11) | 0.0305 (11) | −0.0051 (8) | −0.0099 (8) | 0.0034 (8) |
N1—C1 | 1.321 (3) | N3—C17 | 1.320 (3) |
N1—C8 | 1.358 (3) | N3—C24 | 1.353 (3) |
C1—C2 | 1.430 (3) | C17—C18 | 1.431 (3) |
C1—C9 | 1.464 (3) | C17—C25 | 1.455 (3) |
C2—N2 | 1.328 (3) | C18—N4 | 1.324 (3) |
C2—C13 | 1.454 (3) | C18—C29 | 1.469 (3) |
N2—C3 | 1.371 (3) | N4—C19 | 1.366 (3) |
N2—H1 | 0.85 (3) | N4—H19 | 0.87 (3) |
C3—C8 | 1.398 (3) | C19—C24 | 1.402 (3) |
C3—C4 | 1.401 (3) | C19—C20 | 1.405 (3) |
C4—C5 | 1.375 (3) | C20—C21 | 1.368 (4) |
C4—H4 | 0.95 | C20—H20 | 0.95 |
C5—C6 | 1.405 (4) | C21—C22 | 1.408 (4) |
C5—H5 | 0.95 | C21—H21 | 0.95 |
C6—C7 | 1.366 (4) | C22—C23 | 1.364 (4) |
C6—H6 | 0.95 | C22—H22 | 0.95 |
C7—C8 | 1.414 (3) | C23—C24 | 1.410 (3) |
C7—H7 | 0.95 | C23—H23 | 0.95 |
C9—C10 | 1.376 (3) | C25—C26 | 1.375 (3) |
C9—S1 | 1.726 (2) | C25—S3 | 1.730 (3) |
C10—C11 | 1.413 (4) | C26—C27 | 1.411 (4) |
C10—H10 | 0.95 | C26—H26 | 0.95 |
C11—C12 | 1.359 (4) | C27—C28 | 1.355 (4) |
C11—H11 | 0.95 | C27—H27 | 0.95 |
C12—S1 | 1.707 (3) | C28—S3 | 1.704 (3) |
C12—H12 | 0.95 | C28—H28 | 0.95 |
C13—C14 | 1.391 (4) | C29—C30 | 1.389 (4) |
C13—S2 | 1.722 (3) | C29—S4 | 1.714 (3) |
C14—C15 | 1.409 (4) | C30—C31 | 1.410 (4) |
C14—H14 | 0.95 | C30—H30 | 0.95 |
C15—C16 | 1.355 (4) | C31—C32 | 1.339 (5) |
C15—H15 | 0.95 | C31—H31 | 0.95 |
C16—S2 | 1.705 (3) | C32—S4 | 1.702 (3) |
C16—H16 | 0.95 | C32—H32 | 0.95 |
Cl1—O4 | 1.420 (2) | Cl2—O6 | 1.416 (2) |
Cl1—O2 | 1.425 (2) | Cl2—O5 | 1.435 (2) |
Cl1—O1 | 1.430 (2) | Cl2—O8 | 1.436 (2) |
Cl1—O3 | 1.448 (2) | Cl2—O7 | 1.453 (2) |
C1—N1—C8 | 119.5 (2) | C17—N3—C24 | 119.9 (2) |
N1—C1—C2 | 121.6 (2) | N3—C17—C18 | 120.9 (2) |
N1—C1—C9 | 115.4 (2) | N3—C17—C25 | 115.6 (2) |
C2—C1—C9 | 123.0 (2) | C18—C17—C25 | 123.6 (2) |
N2—C2—C1 | 116.7 (2) | N4—C18—C17 | 117.6 (2) |
N2—C2—C13 | 116.2 (2) | N4—C18—C29 | 117.4 (2) |
C1—C2—C13 | 126.9 (2) | C17—C18—C29 | 125.1 (2) |
C2—N2—C3 | 124.1 (2) | C18—N4—C19 | 123.5 (2) |
C2—N2—H1 | 119 (2) | C18—N4—H19 | 120 (2) |
C3—N2—H1 | 117 (2) | C19—N4—H19 | 117 (2) |
N2—C3—C8 | 116.3 (2) | N4—C19—C24 | 116.7 (2) |
N2—C3—C4 | 121.6 (2) | N4—C19—C20 | 121.6 (2) |
C8—C3—C4 | 122.1 (2) | C24—C19—C20 | 121.7 (2) |
C5—C4—C3 | 117.8 (2) | C21—C20—C19 | 118.0 (2) |
C5—C4—H4 | 121.1 | C21—C20—H20 | 121.0 |
C3—C4—H4 | 121.1 | C19—C20—H20 | 121.0 |
C4—C5—C6 | 120.8 (2) | C20—C21—C22 | 120.9 (2) |
C4—C5—H5 | 119.6 | C20—C21—H21 | 119.5 |
C6—C5—H5 | 119.6 | C22—C21—H21 | 119.5 |
C7—C6—C5 | 121.5 (2) | C23—C22—C21 | 121.2 (2) |
C7—C6—H6 | 119.2 | C23—C22—H22 | 119.4 |
C5—C6—H6 | 119.2 | C21—C22—H22 | 119.4 |
C6—C7—C8 | 119.0 (2) | C22—C23—C24 | 119.3 (2) |
C6—C7—H7 | 120.5 | C22—C23—H23 | 120.4 |
C8—C7—H7 | 120.5 | C24—C23—H23 | 120.4 |
N1—C8—C3 | 121.7 (2) | N3—C24—C19 | 121.5 (2) |
N1—C8—C7 | 119.6 (2) | N3—C24—C23 | 119.8 (2) |
C3—C8—C7 | 118.7 (2) | C19—C24—C23 | 118.8 (2) |
C10—C9—C1 | 130.4 (2) | C26—C25—C17 | 132.6 (2) |
C10—C9—S1 | 110.85 (19) | C26—C25—S3 | 110.25 (19) |
C1—C9—S1 | 118.30 (18) | C17—C25—S3 | 117.06 (18) |
C9—C10—C11 | 112.4 (2) | C25—C26—C27 | 112.9 (2) |
C9—C10—H10 | 123.8 | C25—C26—H26 | 123.6 |
C11—C10—H10 | 123.8 | C27—C26—H26 | 123.6 |
C12—C11—C10 | 113.0 (2) | C28—C27—C26 | 112.9 (2) |
C12—C11—H11 | 123.5 | C28—C27—H27 | 123.6 |
C10—C11—H11 | 123.5 | C26—C27—H27 | 123.6 |
C11—C12—S1 | 111.8 (2) | C27—C28—S3 | 111.9 (2) |
C11—C12—H12 | 124.1 | C27—C28—H28 | 124.0 |
S1—C12—H12 | 124.1 | S3—C28—H28 | 124.0 |
C12—S1—C9 | 91.93 (13) | C28—S3—C25 | 92.08 (13) |
C14—C13—C2 | 124.4 (2) | C30—C29—C18 | 127.4 (2) |
C14—C13—S2 | 111.32 (18) | C30—C29—S4 | 110.85 (19) |
C2—C13—S2 | 124.31 (19) | C18—C29—S4 | 121.73 (19) |
C13—C14—C15 | 111.6 (2) | C29—C30—C31 | 111.7 (3) |
C13—C14—H14 | 124.2 | C29—C30—H30 | 124.2 |
C15—C14—H14 | 124.2 | C31—C30—H30 | 124.2 |
C16—C15—C14 | 113.1 (3) | C32—C31—C30 | 113.1 (3) |
C16—C15—H15 | 123.5 | C32—C31—H31 | 123.4 |
C14—C15—H15 | 123.5 | C30—C31—H31 | 123.4 |
C15—C16—S2 | 112.6 (2) | C31—C32—S4 | 112.6 (2) |
C15—C16—H16 | 123.7 | C31—C32—H32 | 123.7 |
S2—C16—H16 | 123.7 | S4—C32—H32 | 123.7 |
C16—S2—C13 | 91.38 (13) | C32—S4—C29 | 91.67 (14) |
O4—Cl1—O2 | 111.08 (15) | O6—Cl2—O5 | 110.55 (16) |
O4—Cl1—O1 | 109.46 (14) | O6—Cl2—O8 | 110.99 (13) |
O2—Cl1—O1 | 109.68 (16) | O5—Cl2—O8 | 109.70 (14) |
O4—Cl1—O3 | 110.06 (14) | O6—Cl2—O7 | 109.50 (14) |
O2—Cl1—O3 | 108.45 (13) | O5—Cl2—O7 | 108.08 (14) |
O1—Cl1—O3 | 108.05 (14) | O8—Cl2—O7 | 107.93 (12) |
C8—N1—C1—C2 | −0.1 (4) | C24—N3—C17—C18 | −0.1 (4) |
C8—N1—C1—C9 | 177.8 (2) | C24—N3—C17—C25 | −179.9 (2) |
N1—C1—C2—N2 | −1.1 (4) | N3—C17—C18—N4 | 0.5 (4) |
C9—C1—C2—N2 | −178.8 (2) | C25—C17—C18—N4 | −179.7 (2) |
N1—C1—C2—C13 | 174.9 (2) | N3—C17—C18—C29 | −179.3 (2) |
C9—C1—C2—C13 | −2.9 (4) | C25—C17—C18—C29 | 0.5 (4) |
C1—C2—N2—C3 | 0.9 (4) | C17—C18—N4—C19 | −1.4 (4) |
C13—C2—N2—C3 | −175.5 (2) | C29—C18—N4—C19 | 178.5 (2) |
C2—N2—C3—C8 | 0.4 (4) | C18—N4—C19—C24 | 1.7 (4) |
C2—N2—C3—C4 | −179.0 (2) | C18—N4—C19—C20 | −177.2 (2) |
N2—C3—C4—C5 | −178.7 (2) | N4—C19—C20—C21 | −180.0 (2) |
C8—C3—C4—C5 | 2.1 (4) | C24—C19—C20—C21 | 1.3 (4) |
C3—C4—C5—C6 | 0.4 (4) | C19—C20—C21—C22 | 0.8 (4) |
C4—C5—C6—C7 | −1.6 (4) | C20—C21—C22—C23 | −1.6 (4) |
C5—C6—C7—C8 | 0.2 (4) | C21—C22—C23—C24 | 0.3 (4) |
C1—N1—C8—C3 | 1.5 (4) | C17—N3—C24—C19 | 0.4 (4) |
C1—N1—C8—C7 | −177.4 (2) | C17—N3—C24—C23 | −179.4 (2) |
N2—C3—C8—N1 | −1.6 (4) | N4—C19—C24—N3 | −1.2 (4) |
C4—C3—C8—N1 | 177.7 (2) | C20—C19—C24—N3 | 177.7 (2) |
N2—C3—C8—C7 | 177.3 (2) | N4—C19—C24—C23 | 178.6 (2) |
C4—C3—C8—C7 | −3.4 (4) | C20—C19—C24—C23 | −2.5 (4) |
C6—C7—C8—N1 | −178.8 (2) | C22—C23—C24—N3 | −178.5 (2) |
C6—C7—C8—C3 | 2.3 (4) | C22—C23—C24—C19 | 1.7 (4) |
N1—C1—C9—C10 | −142.4 (3) | N3—C17—C25—C26 | −158.7 (3) |
C2—C1—C9—C10 | 35.5 (4) | C18—C17—C25—C26 | 21.4 (4) |
N1—C1—C9—S1 | 29.0 (3) | N3—C17—C25—S3 | 18.0 (3) |
C2—C1—C9—S1 | −153.1 (2) | C18—C17—C25—S3 | −161.8 (2) |
C1—C9—C10—C11 | 171.6 (2) | C17—C25—C26—C27 | 176.8 (3) |
S1—C9—C10—C11 | −0.3 (3) | S3—C25—C26—C27 | −0.1 (3) |
C9—C10—C11—C12 | 1.0 (3) | C25—C26—C27—C28 | 0.5 (4) |
C10—C11—C12—S1 | −1.2 (3) | C26—C27—C28—S3 | −0.7 (3) |
C11—C12—S1—C9 | 0.8 (2) | C27—C28—S3—C25 | 0.6 (2) |
C10—C9—S1—C12 | −0.3 (2) | C26—C25—S3—C28 | −0.3 (2) |
C1—C9—S1—C12 | −173.3 (2) | C17—C25—S3—C28 | −177.7 (2) |
N2—C2—C13—C14 | 54.8 (3) | N4—C18—C29—C30 | 72.1 (4) |
C1—C2—C13—C14 | −121.2 (3) | C17—C18—C29—C30 | −108.1 (3) |
N2—C2—C13—S2 | −125.2 (2) | N4—C18—C29—S4 | −110.3 (2) |
C1—C2—C13—S2 | 58.8 (3) | C17—C18—C29—S4 | 69.5 (3) |
C2—C13—C14—C15 | 178.0 (2) | C18—C29—C30—C31 | 176.1 (3) |
S2—C13—C14—C15 | −2.0 (3) | S4—C29—C30—C31 | −1.7 (3) |
C13—C14—C15—C16 | 2.1 (4) | C29—C30—C31—C32 | 1.9 (4) |
C14—C15—C16—S2 | −1.3 (4) | C30—C31—C32—S4 | −1.2 (4) |
C15—C16—S2—C13 | 0.1 (2) | C31—C32—S4—C29 | 0.2 (3) |
C14—C13—S2—C16 | 1.1 (2) | C30—C29—S4—C32 | 0.9 (2) |
C2—C13—S2—C16 | −178.9 (2) | C18—C29—S4—C32 | −177.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···O3i | 0.85 (3) | 1.90 (3) | 2.728 (3) | 166 (3) |
N4—H19···O7ii | 0.87 (3) | 1.85 (3) | 2.718 (3) | 170 (3) |
Symmetry codes: (i) x−1, y+1, z; (ii) −x+1, −y+1, −z. |