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
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.004 Å
- R factor = 0.057
- wR factor = 0.150
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.04 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl1 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl2 PLAT432_ALERT_2_C Short Inter X...Y Contact O8 .. C18 .. 3.01 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
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. |