Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615012929/wq3091sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012929/wq3091Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012929/wq3091IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012929/wq3091IIIsup4.hkl |
CCDC references: 1410674; 1410673; 1410672
For all compounds, data collection: (CrysAlis PRO; Agilent, 2013); cell refinement: (CrysAlis PRO; Agilent, 2013); data reduction: (CrysAlis PRO; Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Cu(C25H18N6O2S2)](CF3SO3)·0.6CH2Cl2 | F(000) = 3082 |
Mr = 762.14 | Dx = 1.620 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.7107 Å |
a = 16.4083 (9) Å | Cell parameters from 5497 reflections |
b = 17.639 (2) Å | θ = 3.7–28.4° |
c = 21.6604 (13) Å | µ = 1.07 mm−1 |
β = 94.477 (6)° | T = 100 K |
V = 6250.1 (9) Å3 | Block, clear light red |
Z = 8 | 0.10 × 0.07 × 0.05 mm |
Agilent SuperNova Dual Source diffractometer with an Eos detector | 6389 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 4855 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.036 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 26.4°, θmin = 3.0° |
ω scans | h = −20→19 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −22→20 |
Tmin = 0.805, Tmax = 1.000 | l = −27→27 |
19669 measured reflections |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0785P)2 + 19.968P] where P = (Fo2 + 2Fc2)/3 |
6389 reflections | (Δ/σ)max = 0.001 |
433 parameters | Δρmax = 1.12 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | −0.0315 (2) | 0.6238 (2) | 0.64414 (18) | 0.0283 (8) | |
C2 | −0.0416 (2) | 0.7027 (2) | 0.64602 (19) | 0.0345 (9) | |
H2 | −0.0171 | 0.7333 | 0.6178 | 0.041* | |
C3 | −0.0873 (3) | 0.7348 (3) | 0.6892 (2) | 0.0396 (10) | |
H3 | −0.0934 | 0.7872 | 0.6902 | 0.047* | |
C4 | −0.1252 (3) | 0.6897 (3) | 0.73216 (19) | 0.0385 (10) | |
H4 | −0.1561 | 0.7126 | 0.7612 | 0.046* | |
C5 | −0.1171 (2) | 0.6123 (3) | 0.73161 (19) | 0.0356 (9) | |
H5 | −0.1426 | 0.5829 | 0.7601 | 0.043* | |
C6 | −0.0697 (2) | 0.5768 (2) | 0.68752 (18) | 0.0307 (9) | |
C7 | −0.0583 (2) | 0.4976 (2) | 0.68532 (18) | 0.0327 (9) | |
H7 | −0.0839 | 0.4660 | 0.7123 | 0.039* | |
C8 | −0.0094 (2) | 0.4677 (2) | 0.64322 (18) | 0.0308 (9) | |
H8 | 0.0000 | 0.4158 | 0.6417 | 0.037* | |
C9 | 0.0267 (2) | 0.5177 (2) | 0.60201 (18) | 0.0272 (8) | |
C10 | 0.0794 (2) | 0.4922 (2) | 0.55591 (18) | 0.0277 (8) | |
C11 | 0.1519 (2) | 0.4229 (2) | 0.50228 (18) | 0.0299 (8) | |
C12 | 0.2504 (3) | 0.3709 (3) | 0.41701 (19) | 0.0363 (10) | |
H12A | 0.2147 | 0.3933 | 0.3842 | 0.044* | |
H12B | 0.2905 | 0.4084 | 0.4320 | 0.044* | |
C13 | 0.2924 (3) | 0.3009 (3) | 0.3938 (2) | 0.0378 (10) | |
H13A | 0.3249 | 0.2779 | 0.4282 | 0.045* | |
H13B | 0.2510 | 0.2645 | 0.3792 | 0.045* | |
C14 | 0.3469 (3) | 0.3168 (3) | 0.3424 (2) | 0.0424 (11) | |
H14A | 0.3143 | 0.3404 | 0.3084 | 0.051* | |
H14B | 0.3667 | 0.2689 | 0.3275 | 0.051* | |
C15 | 0.4877 (3) | 0.3178 (3) | 0.41623 (19) | 0.0366 (10) | |
C16 | 0.5819 (2) | 0.2907 (2) | 0.48572 (19) | 0.0325 (9) | |
C17 | 0.6537 (2) | 0.2945 (2) | 0.52948 (18) | 0.0313 (9) | |
C18 | 0.7030 (3) | 0.3595 (2) | 0.5387 (2) | 0.0370 (10) | |
H18 | 0.6907 | 0.4041 | 0.5170 | 0.044* | |
C19 | 0.7696 (3) | 0.3549 (2) | 0.5806 (2) | 0.0390 (10) | |
H19 | 0.8032 | 0.3969 | 0.5880 | 0.047* | |
C20 | 0.7873 (3) | 0.2867 (2) | 0.61261 (18) | 0.0339 (9) | |
C21 | 0.8558 (3) | 0.2775 (3) | 0.65626 (19) | 0.0403 (11) | |
H21 | 0.8902 | 0.3185 | 0.6658 | 0.048* | |
C22 | 0.8717 (3) | 0.2093 (3) | 0.68438 (19) | 0.0414 (11) | |
H22 | 0.9173 | 0.2039 | 0.7124 | 0.050* | |
C23 | 0.8192 (3) | 0.1464 (3) | 0.6711 (2) | 0.0389 (10) | |
H23 | 0.8308 | 0.1000 | 0.6902 | 0.047* | |
C24 | 0.7518 (2) | 0.1539 (2) | 0.63057 (18) | 0.0323 (9) | |
H24 | 0.7170 | 0.1128 | 0.6228 | 0.039* | |
C25 | 0.7344 (2) | 0.2237 (2) | 0.60031 (17) | 0.0305 (9) | |
C26 | 0.2043 (3) | 0.0684 (3) | 0.2419 (2) | 0.0450 (11) | |
Cu1 | 0.08010 (3) | 0.64655 (3) | 0.53552 (2) | 0.03214 (17) | |
F2 | 0.13753 (17) | 0.03386 (19) | 0.25902 (14) | 0.0605 (8) | |
F3 | 0.2366 (2) | 0.02553 (19) | 0.19965 (13) | 0.0639 (9) | |
F1 | 0.17975 (18) | 0.13373 (17) | 0.21422 (13) | 0.0558 (8) | |
N1 | 0.01596 (18) | 0.59258 (18) | 0.60146 (14) | 0.0272 (7) | |
N2 | 0.11272 (19) | 0.53696 (18) | 0.51713 (15) | 0.0278 (7) | |
N3 | 0.1610 (2) | 0.49120 (19) | 0.48135 (15) | 0.0303 (7) | |
N5 | 0.53763 (19) | 0.23046 (19) | 0.47625 (15) | 0.0309 (7) | |
N4 | 0.4745 (2) | 0.2478 (2) | 0.43043 (16) | 0.0355 (8) | |
N6 | 0.66716 (19) | 0.22884 (19) | 0.55879 (15) | 0.0293 (7) | |
O1 | 0.10084 (16) | 0.41860 (15) | 0.54919 (12) | 0.0306 (6) | |
O2 | 0.55465 (18) | 0.34928 (16) | 0.44887 (14) | 0.0367 (7) | |
O4 | 0.3441 (2) | 0.1240 (2) | 0.28194 (16) | 0.0497 (8) | |
O5 | 0.2958 (2) | 0.01170 (18) | 0.33211 (15) | 0.0446 (8) | |
O3 | 0.2312 (2) | 0.1334 (2) | 0.34759 (16) | 0.0524 (9) | |
S3 | 0.19173 (7) | 0.33790 (6) | 0.47979 (5) | 0.0388 (3) | |
S2 | 0.43429 (7) | 0.37731 (7) | 0.36357 (6) | 0.0441 (3) | |
S1 | 0.27757 (7) | 0.08669 (6) | 0.30868 (5) | 0.0375 (3) | |
C27 | 0.4216 (5) | 0.4481 (5) | 0.5928 (5) | 0.054 (2) | 0.40 |
H27A | 0.3766 | 0.4183 | 0.6062 | 0.065* | 0.40 |
H27B | 0.4165 | 0.4988 | 0.6093 | 0.065* | 0.40 |
Cl1 | 0.51537 (14) | 0.40773 (13) | 0.62610 (11) | 0.0602 (6) | 0.40 |
Cl2 | 0.41209 (19) | 0.45324 (19) | 0.51679 (12) | 0.0493 (7) | 0.40 |
C27' | 0.4216 (5) | 0.4481 (5) | 0.5928 (5) | 0.054 (2) | 0.20 |
H27C | 0.3817 | 0.4561 | 0.6229 | 0.065* | 0.20 |
H27D | 0.4299 | 0.4944 | 0.5699 | 0.065* | 0.20 |
Cl1' | 0.51537 (14) | 0.40773 (13) | 0.62610 (11) | 0.0602 (6) | 0.20 |
Cl2' | 0.3989 (4) | 0.3701 (5) | 0.5448 (3) | 0.068 (2) | 0.20 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0244 (18) | 0.024 (2) | 0.038 (2) | −0.0023 (16) | 0.0071 (16) | 0.0019 (16) |
C2 | 0.036 (2) | 0.026 (2) | 0.043 (2) | −0.0012 (18) | 0.0124 (18) | 0.0056 (18) |
C3 | 0.040 (2) | 0.030 (2) | 0.050 (2) | 0.002 (2) | 0.0138 (19) | 0.0027 (19) |
C4 | 0.036 (2) | 0.041 (3) | 0.040 (2) | 0.004 (2) | 0.0136 (18) | −0.0009 (19) |
C5 | 0.033 (2) | 0.037 (3) | 0.038 (2) | −0.0054 (19) | 0.0110 (17) | 0.0035 (19) |
C6 | 0.0251 (19) | 0.032 (2) | 0.036 (2) | −0.0047 (17) | 0.0073 (16) | 0.0047 (17) |
C7 | 0.030 (2) | 0.031 (2) | 0.038 (2) | −0.0069 (18) | 0.0065 (16) | 0.0105 (17) |
C8 | 0.029 (2) | 0.022 (2) | 0.042 (2) | −0.0038 (17) | 0.0065 (17) | 0.0061 (17) |
C9 | 0.0251 (18) | 0.020 (2) | 0.0366 (19) | −0.0041 (16) | 0.0061 (15) | 0.0040 (16) |
C10 | 0.0268 (19) | 0.018 (2) | 0.039 (2) | −0.0007 (16) | 0.0048 (16) | 0.0026 (16) |
C11 | 0.036 (2) | 0.020 (2) | 0.035 (2) | −0.0001 (17) | 0.0080 (16) | 0.0006 (16) |
C12 | 0.043 (2) | 0.027 (2) | 0.040 (2) | 0.0033 (19) | 0.0127 (18) | 0.0024 (18) |
C13 | 0.042 (2) | 0.028 (2) | 0.045 (2) | 0.0006 (19) | 0.0076 (19) | −0.0006 (18) |
C14 | 0.050 (3) | 0.036 (3) | 0.041 (2) | 0.009 (2) | 0.008 (2) | 0.001 (2) |
C15 | 0.039 (2) | 0.029 (2) | 0.044 (2) | 0.0043 (19) | 0.0164 (19) | 0.0073 (18) |
C16 | 0.039 (2) | 0.019 (2) | 0.042 (2) | 0.0006 (18) | 0.0197 (18) | 0.0058 (17) |
C17 | 0.040 (2) | 0.021 (2) | 0.036 (2) | −0.0005 (17) | 0.0203 (17) | 0.0004 (16) |
C18 | 0.051 (3) | 0.020 (2) | 0.042 (2) | −0.0044 (19) | 0.021 (2) | 0.0025 (17) |
C19 | 0.054 (3) | 0.024 (2) | 0.042 (2) | −0.014 (2) | 0.022 (2) | −0.0061 (18) |
C20 | 0.041 (2) | 0.029 (2) | 0.035 (2) | −0.0062 (19) | 0.0209 (18) | −0.0045 (17) |
C21 | 0.045 (2) | 0.038 (3) | 0.040 (2) | −0.016 (2) | 0.0175 (19) | −0.0079 (19) |
C22 | 0.042 (2) | 0.047 (3) | 0.036 (2) | −0.005 (2) | 0.0099 (18) | −0.004 (2) |
C23 | 0.044 (2) | 0.033 (3) | 0.042 (2) | −0.004 (2) | 0.0166 (19) | −0.0003 (19) |
C24 | 0.037 (2) | 0.024 (2) | 0.038 (2) | −0.0069 (18) | 0.0142 (17) | −0.0010 (16) |
C25 | 0.037 (2) | 0.024 (2) | 0.0332 (19) | −0.0031 (17) | 0.0205 (17) | −0.0026 (16) |
C26 | 0.049 (3) | 0.035 (3) | 0.052 (3) | 0.009 (2) | 0.013 (2) | 0.005 (2) |
Cu1 | 0.0355 (3) | 0.0168 (3) | 0.0459 (3) | −0.0023 (2) | 0.0147 (2) | 0.0060 (2) |
F2 | 0.0525 (17) | 0.063 (2) | 0.0649 (18) | −0.0121 (15) | −0.0005 (14) | 0.0120 (15) |
F3 | 0.081 (2) | 0.060 (2) | 0.0509 (16) | 0.0222 (17) | 0.0042 (15) | −0.0134 (14) |
F1 | 0.0624 (18) | 0.0471 (18) | 0.0587 (17) | 0.0150 (15) | 0.0093 (14) | 0.0121 (14) |
N1 | 0.0243 (16) | 0.0215 (18) | 0.0364 (17) | −0.0023 (14) | 0.0068 (13) | 0.0026 (13) |
N2 | 0.0273 (16) | 0.0183 (17) | 0.0389 (17) | −0.0005 (13) | 0.0110 (14) | 0.0017 (13) |
N3 | 0.0365 (18) | 0.0194 (18) | 0.0367 (17) | 0.0027 (14) | 0.0128 (14) | 0.0014 (14) |
N5 | 0.0325 (17) | 0.0224 (18) | 0.0397 (18) | 0.0022 (14) | 0.0153 (14) | 0.0057 (14) |
N4 | 0.0351 (18) | 0.0253 (19) | 0.048 (2) | 0.0009 (15) | 0.0127 (15) | 0.0081 (15) |
N6 | 0.0340 (17) | 0.0196 (17) | 0.0370 (17) | −0.0026 (14) | 0.0191 (14) | −0.0001 (13) |
O1 | 0.0372 (15) | 0.0169 (14) | 0.0392 (15) | −0.0029 (12) | 0.0116 (12) | 0.0042 (11) |
O2 | 0.0442 (17) | 0.0211 (16) | 0.0464 (16) | 0.0004 (13) | 0.0147 (13) | 0.0064 (12) |
O4 | 0.0508 (19) | 0.037 (2) | 0.063 (2) | −0.0019 (16) | 0.0172 (16) | 0.0071 (16) |
O5 | 0.0569 (19) | 0.0268 (17) | 0.0504 (18) | 0.0023 (15) | 0.0051 (15) | 0.0037 (14) |
O3 | 0.057 (2) | 0.042 (2) | 0.060 (2) | 0.0087 (17) | 0.0156 (17) | −0.0102 (16) |
S3 | 0.0546 (7) | 0.0206 (5) | 0.0434 (6) | 0.0070 (5) | 0.0176 (5) | 0.0039 (4) |
S2 | 0.0463 (6) | 0.0326 (7) | 0.0552 (7) | 0.0061 (5) | 0.0158 (5) | 0.0170 (5) |
S1 | 0.0432 (6) | 0.0234 (6) | 0.0471 (6) | 0.0031 (5) | 0.0121 (5) | 0.0002 (4) |
C27 | 0.046 (5) | 0.027 (4) | 0.091 (6) | −0.009 (4) | 0.017 (4) | 0.011 (4) |
Cl1 | 0.0572 (13) | 0.0475 (13) | 0.0741 (14) | −0.0047 (10) | −0.0052 (11) | 0.0160 (11) |
Cl2 | 0.0547 (17) | 0.060 (2) | 0.0329 (13) | 0.0178 (15) | −0.0012 (12) | −0.0099 (13) |
C27' | 0.046 (5) | 0.027 (4) | 0.091 (6) | −0.009 (4) | 0.017 (4) | 0.011 (4) |
Cl1' | 0.0572 (13) | 0.0475 (13) | 0.0741 (14) | −0.0047 (10) | −0.0052 (11) | 0.0160 (11) |
Cl2' | 0.058 (4) | 0.078 (5) | 0.066 (4) | −0.020 (4) | 0.001 (3) | 0.015 (4) |
C1—N1 | 1.370 (5) | C16—C17 | 1.454 (6) |
C1—C2 | 1.403 (6) | C17—N6 | 1.331 (5) |
C1—C6 | 1.433 (5) | C17—C18 | 1.409 (6) |
C2—C3 | 1.367 (6) | C18—C19 | 1.368 (7) |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.405 (6) | C19—C20 | 1.407 (6) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.373 (7) | C20—C21 | 1.421 (6) |
C4—H4 | 0.9300 | C20—C25 | 1.422 (6) |
C5—C6 | 1.422 (6) | C21—C22 | 1.365 (7) |
C5—H5 | 0.9300 | C21—H21 | 0.9300 |
C6—C7 | 1.411 (6) | C22—C23 | 1.420 (6) |
C7—C8 | 1.366 (6) | C22—H22 | 0.9300 |
C7—H7 | 0.9300 | C23—C24 | 1.364 (6) |
C8—C9 | 1.417 (5) | C23—H23 | 0.9300 |
C8—H8 | 0.9300 | C24—C25 | 1.414 (6) |
C9—N1 | 1.332 (5) | C24—H24 | 0.9300 |
C9—C10 | 1.444 (5) | C25—N6 | 1.371 (5) |
C10—N2 | 1.304 (5) | C26—F3 | 1.329 (5) |
C10—O1 | 1.356 (5) | C26—F2 | 1.331 (5) |
C11—N3 | 1.300 (5) | C26—F1 | 1.346 (5) |
C11—O1 | 1.368 (5) | C26—S1 | 1.836 (5) |
C11—S3 | 1.721 (4) | Cu1—N5i | 2.046 (3) |
C12—C13 | 1.519 (6) | Cu1—N2 | 2.053 (3) |
C12—S3 | 1.822 (4) | Cu1—N1 | 2.071 (3) |
C12—H12A | 0.9700 | Cu1—N6i | 2.071 (3) |
C12—H12B | 0.9700 | N2—N3 | 1.405 (4) |
C13—C14 | 1.508 (6) | N5—N4 | 1.411 (5) |
C13—H13A | 0.9700 | N5—Cu1ii | 2.046 (3) |
C13—H13B | 0.9700 | N6—Cu1ii | 2.071 (3) |
C14—S2 | 1.818 (5) | O4—S1 | 1.435 (3) |
C14—H14A | 0.9700 | O5—S1 | 1.440 (3) |
C14—H14B | 0.9700 | O3—S1 | 1.438 (3) |
C15—N4 | 1.295 (6) | C27—Cl2 | 1.644 (10) |
C15—O2 | 1.376 (5) | C27—Cl1 | 1.794 (9) |
C15—S2 | 1.736 (4) | C27—H27A | 0.9700 |
C16—N5 | 1.294 (5) | C27—H27B | 0.9700 |
C16—O2 | 1.360 (5) | ||
N1—C1—C2 | 119.5 (4) | C18—C19—C20 | 120.1 (4) |
N1—C1—C6 | 120.7 (4) | C18—C19—H19 | 120.0 |
C2—C1—C6 | 119.7 (4) | C20—C19—H19 | 120.0 |
C3—C2—C1 | 120.2 (4) | C19—C20—C21 | 123.2 (4) |
C3—C2—H2 | 119.9 | C19—C20—C25 | 118.4 (4) |
C1—C2—H2 | 119.9 | C21—C20—C25 | 118.4 (4) |
C2—C3—C4 | 120.9 (4) | C22—C21—C20 | 120.7 (4) |
C2—C3—H3 | 119.6 | C22—C21—H21 | 119.6 |
C4—C3—H3 | 119.6 | C20—C21—H21 | 119.6 |
C5—C4—C3 | 120.6 (4) | C21—C22—C23 | 120.5 (4) |
C5—C4—H4 | 119.7 | C21—C22—H22 | 119.8 |
C3—C4—H4 | 119.7 | C23—C22—H22 | 119.8 |
C4—C5—C6 | 120.1 (4) | C24—C23—C22 | 120.2 (4) |
C4—C5—H5 | 119.9 | C24—C23—H23 | 119.9 |
C6—C5—H5 | 119.9 | C22—C23—H23 | 119.9 |
C7—C6—C5 | 122.6 (4) | C23—C24—C25 | 120.5 (4) |
C7—C6—C1 | 119.0 (4) | C23—C24—H24 | 119.8 |
C5—C6—C1 | 118.4 (4) | C25—C24—H24 | 119.8 |
C8—C7—C6 | 119.4 (4) | N6—C25—C24 | 119.0 (4) |
C8—C7—H7 | 120.3 | N6—C25—C20 | 121.3 (4) |
C6—C7—H7 | 120.3 | C24—C25—C20 | 119.7 (4) |
C7—C8—C9 | 118.4 (4) | F3—C26—F2 | 108.2 (4) |
C7—C8—H8 | 120.8 | F3—C26—F1 | 107.6 (4) |
C9—C8—H8 | 120.8 | F2—C26—F1 | 107.0 (4) |
N1—C9—C8 | 124.1 (4) | F3—C26—S1 | 111.7 (3) |
N1—C9—C10 | 112.9 (3) | F2—C26—S1 | 111.3 (3) |
C8—C9—C10 | 123.0 (4) | F1—C26—S1 | 110.8 (4) |
N2—C10—O1 | 112.7 (3) | N5i—Cu1—N2 | 129.84 (13) |
N2—C10—C9 | 124.1 (4) | N5i—Cu1—N1 | 126.79 (12) |
O1—C10—C9 | 123.2 (3) | N2—Cu1—N1 | 81.67 (13) |
N3—C11—O1 | 113.8 (3) | N5i—Cu1—N6i | 80.81 (14) |
N3—C11—S3 | 130.7 (3) | N2—Cu1—N6i | 121.46 (13) |
O1—C11—S3 | 115.5 (3) | N1—Cu1—N6i | 122.16 (12) |
C13—C12—S3 | 105.5 (3) | C9—N1—C1 | 118.3 (3) |
C13—C12—H12A | 110.6 | C9—N1—Cu1 | 112.8 (2) |
S3—C12—H12A | 110.6 | C1—N1—Cu1 | 128.8 (3) |
C13—C12—H12B | 110.6 | C10—N2—N3 | 106.8 (3) |
S3—C12—H12B | 110.6 | C10—N2—Cu1 | 108.5 (3) |
H12A—C12—H12B | 108.8 | N3—N2—Cu1 | 144.5 (2) |
C14—C13—C12 | 113.8 (4) | C11—N3—N2 | 104.8 (3) |
C14—C13—H13A | 108.8 | C16—N5—N4 | 107.8 (3) |
C12—C13—H13A | 108.8 | C16—N5—Cu1ii | 109.5 (3) |
C14—C13—H13B | 108.8 | N4—N5—Cu1ii | 142.5 (3) |
C12—C13—H13B | 108.8 | C15—N4—N5 | 104.3 (3) |
H13A—C13—H13B | 107.7 | C17—N6—C25 | 117.7 (3) |
C13—C14—S2 | 115.1 (3) | C17—N6—Cu1ii | 114.1 (3) |
C13—C14—H14A | 108.5 | C25—N6—Cu1ii | 128.2 (3) |
S2—C14—H14A | 108.5 | C10—O1—C11 | 101.9 (3) |
C13—C14—H14B | 108.5 | C16—O2—C15 | 102.0 (3) |
S2—C14—H14B | 108.5 | C11—S3—C12 | 99.7 (2) |
H14A—C14—H14B | 107.5 | C15—S2—C14 | 99.1 (2) |
N4—C15—O2 | 113.8 (4) | O4—S1—O3 | 115.4 (2) |
N4—C15—S2 | 130.4 (4) | O4—S1—O5 | 114.8 (2) |
O2—C15—S2 | 115.8 (3) | O3—S1—O5 | 115.1 (2) |
N5—C16—O2 | 112.1 (4) | O4—S1—C26 | 103.6 (2) |
N5—C16—C17 | 123.9 (4) | O3—S1—C26 | 102.6 (2) |
O2—C16—C17 | 124.0 (4) | O5—S1—C26 | 102.8 (2) |
N6—C17—C18 | 124.7 (4) | Cl2—C27—Cl1 | 115.9 (5) |
N6—C17—C16 | 111.5 (4) | Cl2—C27—H27A | 108.3 |
C18—C17—C16 | 123.9 (4) | Cl1—C27—H27A | 108.3 |
C19—C18—C17 | 117.8 (4) | Cl2—C27—H27B | 108.3 |
C19—C18—H18 | 121.1 | Cl1—C27—H27B | 108.3 |
C17—C18—H18 | 121.1 | H27A—C27—H27B | 107.4 |
N1—C1—C2—C3 | −178.6 (4) | N6i—Cu1—N1—C1 | 56.7 (4) |
C6—C1—C2—C3 | 0.3 (6) | O1—C10—N2—N3 | −0.4 (4) |
C1—C2—C3—C4 | −0.3 (7) | C9—C10—N2—N3 | 178.4 (3) |
C2—C3—C4—C5 | 0.0 (7) | O1—C10—N2—Cu1 | −177.0 (2) |
C3—C4—C5—C6 | 0.3 (6) | C9—C10—N2—Cu1 | 1.8 (5) |
C4—C5—C6—C7 | 179.1 (4) | N5i—Cu1—N2—C10 | −133.4 (3) |
C4—C5—C6—C1 | −0.2 (6) | N1—Cu1—N2—C10 | −1.6 (3) |
N1—C1—C6—C7 | −0.6 (6) | N6i—Cu1—N2—C10 | 121.1 (3) |
C2—C1—C6—C7 | −179.5 (4) | N5i—Cu1—N2—N3 | 52.2 (5) |
N1—C1—C6—C5 | 178.8 (3) | N1—Cu1—N2—N3 | −176.1 (4) |
C2—C1—C6—C5 | −0.1 (6) | N6i—Cu1—N2—N3 | −53.3 (5) |
C5—C6—C7—C8 | −177.5 (4) | O1—C11—N3—N2 | 0.4 (4) |
C1—C6—C7—C8 | 1.9 (6) | S3—C11—N3—N2 | 179.0 (3) |
C6—C7—C8—C9 | −1.6 (6) | C10—N2—N3—C11 | 0.0 (4) |
C7—C8—C9—N1 | −0.1 (6) | Cu1—N2—N3—C11 | 174.5 (4) |
C7—C8—C9—C10 | 179.8 (4) | O2—C16—N5—N4 | −0.8 (4) |
N1—C9—C10—N2 | −0.7 (5) | C17—C16—N5—N4 | −179.3 (3) |
C8—C9—C10—N2 | 179.4 (4) | O2—C16—N5—Cu1ii | −177.9 (2) |
N1—C9—C10—O1 | 178.0 (3) | C17—C16—N5—Cu1ii | 3.6 (5) |
C8—C9—C10—O1 | −1.9 (6) | O2—C15—N4—N5 | −0.1 (4) |
S3—C12—C13—C14 | −178.2 (3) | S2—C15—N4—N5 | −179.6 (3) |
C12—C13—C14—S2 | 64.0 (5) | C16—N5—N4—C15 | 0.5 (4) |
N5—C16—C17—N6 | −0.7 (5) | Cu1ii—N5—N4—C15 | 176.1 (3) |
O2—C16—C17—N6 | −179.0 (3) | C18—C17—N6—C25 | −0.9 (5) |
N5—C16—C17—C18 | 178.4 (4) | C16—C17—N6—C25 | 178.2 (3) |
O2—C16—C17—C18 | 0.1 (6) | C18—C17—N6—Cu1ii | 178.2 (3) |
N6—C17—C18—C19 | 0.2 (6) | C16—C17—N6—Cu1ii | −2.6 (4) |
C16—C17—C18—C19 | −178.9 (4) | C24—C25—N6—C17 | −177.9 (3) |
C17—C18—C19—C20 | 0.4 (6) | C20—C25—N6—C17 | 1.1 (5) |
C18—C19—C20—C21 | 179.3 (4) | C24—C25—N6—Cu1ii | 3.1 (5) |
C18—C19—C20—C25 | −0.2 (6) | C20—C25—N6—Cu1ii | −177.9 (3) |
C19—C20—C21—C22 | −177.7 (4) | N2—C10—O1—C11 | 0.6 (4) |
C25—C20—C21—C22 | 1.8 (6) | C9—C10—O1—C11 | −178.3 (4) |
C20—C21—C22—C23 | −0.9 (6) | N3—C11—O1—C10 | −0.6 (4) |
C21—C22—C23—C24 | −0.6 (6) | S3—C11—O1—C10 | −179.5 (3) |
C22—C23—C24—C25 | 1.3 (6) | N5—C16—O2—C15 | 0.7 (4) |
C23—C24—C25—N6 | 178.6 (3) | C17—C16—O2—C15 | 179.2 (4) |
C23—C24—C25—C20 | −0.4 (6) | N4—C15—O2—C16 | −0.3 (4) |
C19—C20—C25—N6 | −0.6 (5) | S2—C15—O2—C16 | 179.2 (3) |
C21—C20—C25—N6 | 179.9 (3) | N3—C11—S3—C12 | −0.5 (5) |
C19—C20—C25—C24 | 178.4 (4) | O1—C11—S3—C12 | 178.2 (3) |
C21—C20—C25—C24 | −1.1 (5) | C13—C12—S3—C11 | 177.9 (3) |
C8—C9—N1—C1 | 1.4 (6) | N4—C15—S2—C14 | 7.6 (5) |
C10—C9—N1—C1 | −178.5 (3) | O2—C15—S2—C14 | −171.9 (3) |
C8—C9—N1—Cu1 | 179.1 (3) | C13—C14—S2—C15 | 65.7 (4) |
C10—C9—N1—Cu1 | −0.8 (4) | F3—C26—S1—O4 | 59.3 (4) |
C2—C1—N1—C9 | 177.9 (4) | F2—C26—S1—O4 | −179.6 (3) |
C6—C1—N1—C9 | −1.0 (5) | F1—C26—S1—O4 | −60.7 (4) |
C2—C1—N1—Cu1 | 0.6 (5) | F3—C26—S1—O3 | 179.6 (3) |
C6—C1—N1—Cu1 | −178.3 (3) | F2—C26—S1—O3 | −59.2 (4) |
N5i—Cu1—N1—C9 | 135.7 (3) | F1—C26—S1—O3 | 59.7 (4) |
N2—Cu1—N1—C9 | 1.4 (3) | F3—C26—S1—O5 | −60.6 (4) |
N6i—Cu1—N1—C9 | −120.7 (3) | F2—C26—S1—O5 | 60.6 (4) |
N5i—Cu1—N1—C1 | −46.9 (4) | F1—C26—S1—O5 | 179.5 (3) |
N2—Cu1—N1—C1 | 178.8 (3) |
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x+1/2, y−1/2, z. |
[Cu2(C26H20N6O2S2)2](BF4)2·1.5CH2Cl2·CH4O | Z = 1 |
Mr = 1485.33 | F(000) = 753 |
Triclinic, P1 | Dx = 1.559 Mg m−3 |
a = 11.1554 (8) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 11.5090 (9) Å | Cell parameters from 3813 reflections |
c = 13.6722 (11) Å | θ = 3.6–26.5° |
α = 68.550 (8)° | µ = 1.01 mm−1 |
β = 81.603 (6)° | T = 100 K |
γ = 76.089 (6)° | Plate, clear light orange |
V = 1582.6 (2) Å3 | 0.21 × 0.15 × 0.02 mm |
Agilent SuperNova Dual Source diffractometer with an Eos detector | 6460 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 4665 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.037 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 26.4°, θmin = 2.9° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −14→14 |
Tmin = 0.727, Tmax = 1.000 | l = −16→17 |
12689 measured reflections |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0997P)2 + 1.9848P] where P = (Fo2 + 2Fc2)/3 |
6460 reflections | (Δ/σ)max = 0.002 |
487 parameters | Δρmax = 1.43 e Å−3 |
34 restraints | Δρmin = −0.48 e Å−3 |
Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
B1 | 0.9522 (8) | 0.4239 (9) | 0.1419 (7) | 0.041 (3) | 0.50 |
B2 | 0.5000 | 1.0000 | 1.0000 | 0.0326 (16) | |
C1 | −0.0941 (4) | 1.1288 (4) | 1.0411 (3) | 0.0291 (9) | |
C2 | −0.2128 (4) | 1.1011 (4) | 1.0727 (4) | 0.0360 (11) | |
H2 | −0.2697 | 1.1214 | 1.0227 | 0.043* | |
C3 | −0.2443 (5) | 1.0444 (5) | 1.1769 (4) | 0.0439 (12) | |
H3 | −0.3228 | 1.0259 | 1.1972 | 0.053* | |
C4 | −0.1599 (5) | 1.0134 (5) | 1.2542 (4) | 0.0453 (13) | |
H4 | −0.1837 | 0.9758 | 1.3248 | 0.054* | |
C5 | −0.0434 (5) | 1.0379 (4) | 1.2265 (4) | 0.0396 (11) | |
H5 | 0.0118 | 1.0167 | 1.2780 | 0.048* | |
C6 | −0.0068 (4) | 1.0958 (4) | 1.1191 (4) | 0.0334 (10) | |
C7 | 0.1123 (4) | 1.1214 (4) | 1.0853 (4) | 0.0358 (11) | |
H7 | 0.1707 | 1.1006 | 1.1342 | 0.043* | |
C8 | 0.1423 (4) | 1.1770 (4) | 0.9802 (4) | 0.0332 (10) | |
H8 | 0.2206 | 1.1950 | 0.9565 | 0.040* | |
C9 | 0.0517 (4) | 1.2059 (4) | 0.9096 (3) | 0.0296 (9) | |
C10 | 0.0729 (4) | 1.2651 (4) | 0.7962 (3) | 0.0289 (9) | |
C11 | 0.1645 (4) | 1.3357 (5) | 0.6468 (4) | 0.0366 (11) | |
C12 | 0.2231 (5) | 1.4265 (5) | 0.4380 (4) | 0.0472 (13) | |
H12A | 0.1432 | 1.4819 | 0.4418 | 0.057* | |
H12B | 0.2750 | 1.4760 | 0.3832 | 0.057* | |
C13 | 0.2055 (5) | 1.3176 (5) | 0.4077 (4) | 0.0455 (12) | |
H13A | 0.1639 | 1.3528 | 0.3425 | 0.055* | |
H13B | 0.1520 | 1.2693 | 0.4617 | 0.055* | |
C14 | 0.3263 (5) | 1.2267 (5) | 0.3935 (4) | 0.0469 (13) | |
H14A | 0.3814 | 1.2741 | 0.3406 | 0.056* | |
H14B | 0.3669 | 1.1876 | 0.4592 | 0.056* | |
C15 | 0.2996 (5) | 1.1232 (5) | 0.3594 (4) | 0.0477 (13) | |
H15A | 0.2634 | 1.1615 | 0.2917 | 0.057* | |
H15B | 0.2415 | 1.0782 | 0.4104 | 0.057* | |
C16 | 0.3865 (4) | 0.9176 (5) | 0.3029 (4) | 0.0361 (11) | |
C17 | 0.3920 (4) | 0.7692 (4) | 0.2457 (3) | 0.0331 (10) | |
C18 | 0.4356 (4) | 0.6592 (4) | 0.2110 (3) | 0.0343 (10) | |
C19 | 0.5598 (5) | 0.5973 (6) | 0.2077 (4) | 0.0482 (13) | |
H19 | 0.6211 | 0.6268 | 0.2258 | 0.058* | |
C20 | 0.5886 (5) | 0.4942 (6) | 0.1778 (5) | 0.0573 (16) | |
H20 | 0.6702 | 0.4502 | 0.1767 | 0.069* | |
C21 | 0.4943 (5) | 0.4526 (5) | 0.1478 (4) | 0.0491 (14) | |
C22 | 0.3707 (5) | 0.5232 (4) | 0.1494 (4) | 0.0368 (11) | |
C23 | 0.2739 (6) | 0.4871 (5) | 0.1186 (4) | 0.0484 (13) | |
H23 | 0.1931 | 0.5333 | 0.1195 | 0.058* | |
C24 | 0.3013 (7) | 0.3822 (5) | 0.0872 (5) | 0.0593 (17) | |
H24 | 0.2384 | 0.3584 | 0.0657 | 0.071* | |
C25 | 0.4215 (8) | 0.3111 (5) | 0.0871 (5) | 0.069 (2) | |
H25 | 0.4372 | 0.2394 | 0.0673 | 0.083* | |
C26 | 0.5157 (7) | 0.3447 (5) | 0.1153 (5) | 0.0627 (18) | |
H26 | 0.5955 | 0.2968 | 0.1135 | 0.075* | |
C27 | 0.8604 (10) | 0.2512 (15) | 0.4852 (19) | 0.063 (5) | 0.50 |
H27A | 0.8967 | 0.3211 | 0.4365 | 0.075* | 0.50 |
H27B | 0.8614 | 0.2533 | 0.5553 | 0.075* | 0.50 |
C28 | 0.9396 (16) | 0.3811 (15) | 0.1973 (14) | 0.084 (5) | 0.50 |
H28A | 0.9368 | 0.3595 | 0.2722 | 0.127* | 0.50 |
H28B | 1.0206 | 0.3469 | 0.1726 | 0.127* | 0.50 |
H28C | 0.8793 | 0.3459 | 0.1800 | 0.127* | 0.50 |
C27' | 0.8070 (16) | 0.268 (3) | 0.3937 (11) | 0.063 (5) | 0.25 |
H27C | 0.7926 | 0.3560 | 0.3458 | 0.075* | 0.25 |
H27D | 0.8646 | 0.2178 | 0.3572 | 0.075* | 0.25 |
Cl1 | 0.9543 (4) | 0.1122 (4) | 0.4801 (3) | 0.0832 (11) | 0.50 |
Cl2 | 0.7078 (5) | 0.2804 (5) | 0.4571 (4) | 0.1066 (15) | 0.50 |
Cl1' | 0.6702 (5) | 0.2176 (5) | 0.4186 (4) | 0.0469 (13) | 0.25 |
Cl2' | 0.8778 (6) | 0.2622 (8) | 0.4995 (6) | 0.0486 (17) | 0.25 |
Cu1 | 0.17336 (5) | 0.74743 (5) | 0.18837 (5) | 0.0344 (2) | |
F1 | 0.885 (2) | 0.500 (2) | 0.1974 (16) | 0.100 (7) | 0.50 |
F2 | 1.0100 (8) | 0.5000 (9) | 0.0527 (6) | 0.092 (3) | 0.50 |
F3 | 1.0390 (6) | 0.3304 (6) | 0.2065 (5) | 0.0524 (15) | 0.50 |
F4 | 0.8734 (6) | 0.3674 (6) | 0.1137 (6) | 0.0619 (19) | 0.50 |
F5 | 0.5381 (10) | 1.0164 (9) | 1.0826 (7) | 0.099 (3) | 0.50 |
F6 | 0.4451 (7) | 0.9003 (7) | 1.0327 (6) | 0.067 (2) | 0.50 |
F7 | 0.6029 (6) | 0.9793 (7) | 0.9324 (6) | 0.069 (2) | 0.50 |
F8 | 0.4267 (7) | 1.1114 (7) | 0.9391 (6) | 0.079 (2) | 0.50 |
N1 | −0.0099 (3) | 1.3038 (3) | 0.7288 (3) | 0.0327 (8) | |
N2 | 0.0500 (4) | 1.3506 (4) | 0.6289 (3) | 0.0377 (9) | |
N3 | −0.0629 (3) | 1.1840 (3) | 0.9361 (3) | 0.0266 (8) | |
N4 | 0.3424 (3) | 0.6261 (3) | 0.1831 (3) | 0.0302 (8) | |
N5 | 0.2788 (3) | 0.8281 (3) | 0.2460 (3) | 0.0307 (8) | |
N6 | 0.2734 (4) | 0.9278 (4) | 0.2842 (3) | 0.0356 (9) | |
O1 | 0.1875 (3) | 1.2811 (3) | 0.7509 (2) | 0.0333 (7) | |
O2 | 0.4683 (3) | 0.8191 (3) | 0.2815 (3) | 0.0380 (8) | |
O3 | 0.915 (3) | 0.507 (2) | 0.1515 (17) | 0.097 (8) | 0.50 |
H3A | 0.8865 | 0.5265 | 0.0944 | 0.146* | 0.50 |
S1 | 0.29281 (12) | 1.37416 (14) | 0.56289 (10) | 0.0454 (3) | |
S2 | 0.44522 (12) | 1.01202 (13) | 0.35022 (11) | 0.0442 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
B1 | 0.038 (5) | 0.040 (5) | 0.041 (5) | −0.007 (4) | 0.001 (4) | −0.013 (4) |
B2 | 0.025 (4) | 0.035 (4) | 0.040 (4) | −0.002 (3) | 0.001 (3) | −0.019 (3) |
C1 | 0.032 (2) | 0.024 (2) | 0.034 (2) | 0.0005 (17) | −0.0018 (19) | −0.0171 (19) |
C2 | 0.031 (2) | 0.032 (2) | 0.043 (3) | 0.0036 (19) | 0.000 (2) | −0.018 (2) |
C3 | 0.038 (3) | 0.042 (3) | 0.049 (3) | −0.003 (2) | 0.007 (2) | −0.020 (2) |
C4 | 0.050 (3) | 0.041 (3) | 0.036 (3) | 0.003 (2) | 0.002 (2) | −0.012 (2) |
C5 | 0.044 (3) | 0.037 (3) | 0.035 (3) | 0.003 (2) | −0.008 (2) | −0.013 (2) |
C6 | 0.037 (3) | 0.028 (2) | 0.036 (2) | 0.0046 (19) | −0.006 (2) | −0.017 (2) |
C7 | 0.033 (2) | 0.037 (2) | 0.038 (3) | 0.002 (2) | −0.012 (2) | −0.015 (2) |
C8 | 0.026 (2) | 0.035 (2) | 0.043 (3) | −0.0017 (19) | −0.009 (2) | −0.019 (2) |
C9 | 0.030 (2) | 0.029 (2) | 0.032 (2) | −0.0014 (18) | −0.0034 (18) | −0.0163 (19) |
C10 | 0.025 (2) | 0.028 (2) | 0.036 (2) | −0.0023 (17) | −0.0016 (18) | −0.0157 (19) |
C11 | 0.036 (3) | 0.041 (3) | 0.032 (3) | −0.007 (2) | −0.007 (2) | −0.011 (2) |
C12 | 0.042 (3) | 0.061 (3) | 0.037 (3) | −0.014 (3) | −0.003 (2) | −0.012 (3) |
C13 | 0.038 (3) | 0.064 (3) | 0.037 (3) | −0.007 (3) | −0.009 (2) | −0.019 (3) |
C14 | 0.045 (3) | 0.058 (3) | 0.041 (3) | −0.016 (3) | −0.002 (2) | −0.018 (3) |
C15 | 0.043 (3) | 0.062 (3) | 0.047 (3) | −0.013 (3) | −0.007 (2) | −0.026 (3) |
C16 | 0.035 (3) | 0.044 (3) | 0.030 (2) | −0.013 (2) | −0.005 (2) | −0.010 (2) |
C17 | 0.030 (2) | 0.043 (3) | 0.027 (2) | −0.010 (2) | −0.0080 (18) | −0.008 (2) |
C18 | 0.028 (2) | 0.041 (3) | 0.027 (2) | 0.002 (2) | −0.0012 (18) | −0.009 (2) |
C19 | 0.025 (2) | 0.067 (4) | 0.045 (3) | 0.003 (2) | −0.007 (2) | −0.016 (3) |
C20 | 0.038 (3) | 0.063 (4) | 0.050 (3) | 0.020 (3) | −0.006 (3) | −0.013 (3) |
C21 | 0.052 (3) | 0.040 (3) | 0.036 (3) | 0.010 (2) | 0.006 (2) | −0.007 (2) |
C22 | 0.043 (3) | 0.028 (2) | 0.031 (2) | −0.001 (2) | 0.004 (2) | −0.0061 (19) |
C23 | 0.058 (4) | 0.040 (3) | 0.051 (3) | −0.010 (3) | 0.008 (3) | −0.024 (3) |
C24 | 0.087 (5) | 0.041 (3) | 0.055 (4) | −0.022 (3) | 0.020 (3) | −0.026 (3) |
C25 | 0.117 (6) | 0.029 (3) | 0.050 (4) | −0.001 (3) | 0.013 (4) | −0.018 (3) |
C26 | 0.079 (5) | 0.038 (3) | 0.045 (3) | 0.021 (3) | 0.007 (3) | −0.010 (3) |
C27 | 0.060 (6) | 0.079 (6) | 0.059 (6) | −0.030 (4) | −0.010 (4) | −0.023 (4) |
C28 | 0.072 (11) | 0.068 (10) | 0.087 (13) | −0.003 (9) | 0.010 (10) | −0.009 (10) |
C27' | 0.060 (6) | 0.079 (6) | 0.059 (6) | −0.030 (4) | −0.010 (4) | −0.023 (4) |
Cl1 | 0.083 (2) | 0.129 (3) | 0.0497 (17) | −0.055 (2) | 0.0073 (16) | −0.0284 (18) |
Cl2 | 0.104 (3) | 0.109 (3) | 0.078 (2) | −0.046 (2) | −0.022 (2) | 0.023 (2) |
Cl1' | 0.044 (3) | 0.057 (3) | 0.039 (3) | −0.033 (2) | −0.008 (2) | 0.000 (2) |
Cl2' | 0.040 (3) | 0.089 (5) | 0.031 (3) | −0.033 (3) | −0.003 (2) | −0.026 (3) |
Cu1 | 0.0253 (3) | 0.0394 (4) | 0.0416 (4) | −0.0007 (2) | −0.0082 (2) | −0.0188 (3) |
F1 | 0.094 (8) | 0.079 (9) | 0.157 (19) | −0.019 (6) | 0.013 (11) | −0.084 (13) |
F2 | 0.065 (5) | 0.110 (7) | 0.068 (5) | −0.022 (5) | −0.009 (4) | 0.011 (5) |
F3 | 0.049 (4) | 0.065 (4) | 0.046 (4) | −0.019 (3) | −0.011 (3) | −0.016 (3) |
F4 | 0.046 (4) | 0.056 (4) | 0.099 (5) | 0.010 (3) | −0.024 (4) | −0.051 (4) |
F5 | 0.154 (9) | 0.103 (6) | 0.072 (6) | −0.061 (7) | −0.022 (6) | −0.039 (5) |
F6 | 0.080 (5) | 0.067 (4) | 0.056 (4) | −0.046 (4) | −0.006 (4) | −0.003 (4) |
F7 | 0.034 (3) | 0.077 (5) | 0.060 (4) | 0.013 (3) | 0.005 (3) | −0.002 (4) |
F8 | 0.052 (4) | 0.063 (4) | 0.077 (5) | 0.017 (4) | 0.014 (4) | 0.003 (4) |
N1 | 0.030 (2) | 0.033 (2) | 0.034 (2) | −0.0022 (16) | −0.0043 (16) | −0.0124 (17) |
N2 | 0.036 (2) | 0.043 (2) | 0.032 (2) | −0.0080 (18) | −0.0017 (17) | −0.0103 (18) |
N3 | 0.0268 (19) | 0.0236 (17) | 0.032 (2) | −0.0001 (14) | −0.0053 (15) | −0.0142 (15) |
N4 | 0.0259 (19) | 0.0298 (19) | 0.0292 (19) | −0.0004 (15) | −0.0021 (15) | −0.0069 (16) |
N5 | 0.028 (2) | 0.0300 (19) | 0.035 (2) | −0.0012 (16) | −0.0079 (16) | −0.0136 (16) |
N6 | 0.036 (2) | 0.040 (2) | 0.035 (2) | −0.0073 (18) | −0.0079 (17) | −0.0162 (18) |
O1 | 0.0270 (16) | 0.0407 (18) | 0.0332 (17) | −0.0071 (14) | −0.0017 (13) | −0.0141 (14) |
O2 | 0.0293 (17) | 0.0470 (19) | 0.0384 (19) | −0.0081 (15) | −0.0076 (14) | −0.0133 (15) |
O3 | 0.15 (2) | 0.036 (7) | 0.110 (16) | −0.003 (10) | −0.046 (14) | −0.028 (9) |
S1 | 0.0382 (7) | 0.0649 (9) | 0.0371 (7) | −0.0176 (6) | 0.0002 (5) | −0.0189 (6) |
S2 | 0.0400 (7) | 0.0553 (8) | 0.0455 (7) | −0.0160 (6) | −0.0075 (6) | −0.0210 (6) |
B1—F4 | 1.378 (7) | C18—N4 | 1.336 (6) |
B1—F1 | 1.385 (8) | C18—C19 | 1.400 (7) |
B1—F3 | 1.389 (7) | C19—C20 | 1.347 (8) |
B1—F2 | 1.390 (7) | C19—H19 | 0.9300 |
B1—H3A | 1.2309 | C20—C21 | 1.419 (9) |
B2—F6i | 1.332 (6) | C20—H20 | 0.9300 |
B2—F6 | 1.332 (6) | C21—C22 | 1.424 (7) |
B2—F5 | 1.352 (7) | C21—C26 | 1.424 (8) |
B2—F5i | 1.352 (7) | C22—N4 | 1.375 (6) |
B2—F8i | 1.385 (7) | C22—C23 | 1.412 (8) |
B2—F8 | 1.385 (7) | C23—C24 | 1.378 (7) |
B2—F7i | 1.396 (6) | C23—H23 | 0.9300 |
B2—F7 | 1.396 (6) | C24—C25 | 1.393 (10) |
C1—N3 | 1.371 (6) | C24—H24 | 0.9300 |
C1—C2 | 1.405 (6) | C25—C26 | 1.351 (10) |
C1—C6 | 1.435 (6) | C25—H25 | 0.9300 |
C2—C3 | 1.365 (7) | C26—H26 | 0.9300 |
C2—H2 | 0.9300 | C27—Cl1 | 1.708 (10) |
C3—C4 | 1.408 (7) | C27—Cl2 | 1.725 (9) |
C3—H3 | 0.9300 | C27—H27A | 0.9700 |
C4—C5 | 1.366 (8) | C27—H27B | 0.9700 |
C4—H4 | 0.9300 | C28—O3 | 1.33 (3) |
C5—C6 | 1.416 (7) | C28—H28A | 0.9600 |
C5—H5 | 0.9300 | C28—H28B | 0.9600 |
C6—C7 | 1.406 (7) | C28—H28C | 0.9600 |
C7—C8 | 1.370 (7) | C27'—Cl1' | 1.709 (10) |
C7—H7 | 0.9300 | C27'—Cl2' | 1.718 (10) |
C8—C9 | 1.397 (6) | C27'—H27C | 0.9700 |
C8—H8 | 0.9300 | C27'—H27D | 0.9700 |
C9—N3 | 1.335 (6) | Cl1—Cl1ii | 2.423 (10) |
C9—C10 | 1.456 (6) | Cu1—N5 | 2.048 (4) |
C10—N1 | 1.285 (6) | Cu1—N3iii | 2.049 (3) |
C10—O1 | 1.361 (5) | Cu1—N4 | 2.069 (4) |
C11—N2 | 1.295 (6) | Cu1—N1iii | 2.093 (4) |
C11—O1 | 1.364 (5) | F1—H3A | 1.3268 |
C11—S1 | 1.737 (5) | F2—F2iv | 1.489 (18) |
C12—C13 | 1.517 (7) | F2—H3A | 1.4182 |
C12—S1 | 1.815 (5) | F5—F6i | 1.528 (11) |
C12—H12A | 0.9700 | F5—F8i | 1.553 (12) |
C12—H12B | 0.9700 | F5—F7i | 1.603 (12) |
C13—C14 | 1.531 (7) | F6—F8i | 1.497 (10) |
C13—H13A | 0.9700 | F6—F5i | 1.528 (11) |
C13—H13B | 0.9700 | F6—F7i | 1.577 (11) |
C14—C15 | 1.530 (7) | F7—F6i | 1.577 (11) |
C14—H14A | 0.9700 | F7—F5i | 1.603 (12) |
C14—H14B | 0.9700 | F7—F8i | 1.715 (10) |
C15—S2 | 1.830 (6) | F8—F6i | 1.497 (10) |
C15—H15A | 0.9700 | F8—F5i | 1.553 (12) |
C15—H15B | 0.9700 | F8—F7i | 1.715 (10) |
C16—N6 | 1.293 (6) | N1—N2 | 1.404 (5) |
C16—O2 | 1.368 (6) | N1—Cu1iii | 2.093 (4) |
C16—S2 | 1.735 (5) | N3—Cu1iii | 2.049 (3) |
C17—N5 | 1.282 (6) | N5—N6 | 1.411 (5) |
C17—O2 | 1.362 (5) | O3—H3A | 0.8200 |
C17—C18 | 1.463 (6) | ||
F4—B1—F1 | 109.3 (12) | O2—C17—C18 | 123.0 (4) |
F4—B1—F3 | 109.6 (7) | N4—C18—C19 | 124.7 (4) |
F1—B1—F3 | 108.4 (13) | N4—C18—C17 | 111.5 (4) |
F4—B1—F2 | 110.3 (8) | C19—C18—C17 | 123.8 (5) |
F1—B1—F2 | 108.3 (11) | C20—C19—C18 | 118.5 (5) |
F3—B1—F2 | 110.8 (7) | C20—C19—H19 | 120.7 |
F4—B1—H3A | 86.5 | C18—C19—H19 | 120.7 |
F1—B1—H3A | 60.6 | C19—C20—C21 | 119.9 (5) |
F3—B1—H3A | 163.4 | C19—C20—H20 | 120.0 |
F2—B1—H3A | 65.2 | C21—C20—H20 | 120.0 |
F6i—B2—F6 | 180.000 (3) | C20—C21—C22 | 118.4 (5) |
F6i—B2—F5 | 69.4 (5) | C20—C21—C26 | 124.0 (6) |
F6—B2—F5 | 110.6 (5) | C22—C21—C26 | 117.7 (6) |
F6i—B2—F5i | 110.6 (5) | N4—C22—C23 | 118.5 (4) |
F6—B2—F5i | 69.4 (5) | N4—C22—C21 | 120.9 (5) |
F5—B2—F5i | 180.000 (5) | C23—C22—C21 | 120.6 (5) |
F6i—B2—F8i | 113.1 (5) | C24—C23—C22 | 118.7 (6) |
F6—B2—F8i | 66.9 (5) | C24—C23—H23 | 120.6 |
F5—B2—F8i | 69.1 (6) | C22—C23—H23 | 120.6 |
F5i—B2—F8i | 110.9 (6) | C23—C24—C25 | 121.2 (6) |
F6i—B2—F8 | 66.9 (5) | C23—C24—H24 | 119.4 |
F6—B2—F8 | 113.1 (5) | C25—C24—H24 | 119.4 |
F5—B2—F8 | 110.9 (6) | C26—C25—C24 | 121.0 (5) |
F5i—B2—F8 | 69.1 (6) | C26—C25—H25 | 119.5 |
F8i—B2—F8 | 180.000 (3) | C24—C25—H25 | 119.5 |
F6i—B2—F7i | 109.4 (5) | C25—C26—C21 | 120.8 (6) |
F6—B2—F7i | 70.6 (5) | C25—C26—H26 | 119.6 |
F5—B2—F7i | 71.3 (5) | C21—C26—H26 | 119.6 |
F5i—B2—F7i | 108.7 (5) | Cl1—C27—Cl2 | 118.0 (8) |
F8i—B2—F7i | 103.9 (4) | Cl1—C27—H27A | 107.8 |
F8—B2—F7i | 76.1 (4) | Cl2—C27—H27A | 107.8 |
F6i—B2—F7 | 70.6 (5) | Cl1—C27—H27B | 107.8 |
F6—B2—F7 | 109.4 (5) | Cl2—C27—H27B | 107.8 |
F5—B2—F7 | 108.7 (5) | H27A—C27—H27B | 107.2 |
F5i—B2—F7 | 71.3 (5) | O3—C28—H28A | 109.5 |
F8i—B2—F7 | 76.1 (4) | O3—C28—H28B | 109.5 |
F8—B2—F7 | 103.9 (4) | H28A—C28—H28B | 109.5 |
F7i—B2—F7 | 180.000 (2) | O3—C28—H28C | 109.5 |
N3—C1—C2 | 119.4 (4) | H28A—C28—H28C | 109.5 |
N3—C1—C6 | 121.2 (4) | H28B—C28—H28C | 109.5 |
C2—C1—C6 | 119.4 (4) | Cl1'—C27'—Cl2' | 117.6 (9) |
C3—C2—C1 | 119.9 (5) | Cl1'—C27'—H27C | 107.9 |
C3—C2—H2 | 120.0 | Cl2'—C27'—H27C | 107.9 |
C1—C2—H2 | 120.0 | Cl1'—C27'—H27D | 107.9 |
C2—C3—C4 | 121.1 (5) | Cl2'—C27'—H27D | 107.9 |
C2—C3—H3 | 119.5 | H27C—C27'—H27D | 107.2 |
C4—C3—H3 | 119.5 | C27—Cl1—Cl1ii | 162.2 (9) |
C5—C4—C3 | 120.7 (5) | N5—Cu1—N3iii | 133.56 (14) |
C5—C4—H4 | 119.7 | N5—Cu1—N4 | 80.91 (14) |
C3—C4—H4 | 119.7 | N3iii—Cu1—N4 | 120.30 (14) |
C4—C5—C6 | 119.9 (5) | N5—Cu1—N1iii | 120.47 (15) |
C4—C5—H5 | 120.0 | N3iii—Cu1—N1iii | 81.60 (15) |
C6—C5—H5 | 120.0 | N4—Cu1—N1iii | 126.66 (14) |
C7—C6—C5 | 122.7 (4) | B1—F1—H3A | 53.9 |
C7—C6—C1 | 118.3 (4) | B1—F2—F2iv | 119.2 (10) |
C5—C6—C1 | 118.9 (4) | B1—F2—H3A | 52.0 |
C8—C7—C6 | 120.0 (4) | F2iv—F2—H3A | 101.5 |
C8—C7—H7 | 120.0 | B2—F5—F6i | 54.7 (4) |
C6—C7—H7 | 120.0 | B2—F5—F8i | 56.4 (4) |
C7—C8—C9 | 117.9 (4) | F6i—F5—F8i | 94.8 (6) |
C7—C8—H8 | 121.0 | B2—F5—F7i | 55.6 (4) |
C9—C8—H8 | 121.0 | F6i—F5—F7i | 90.7 (6) |
N3—C9—C8 | 125.3 (4) | F8i—F5—F7i | 87.9 (6) |
N3—C9—C10 | 111.9 (4) | B2—F6—F8i | 58.3 (4) |
C8—C9—C10 | 122.8 (4) | B2—F6—F5i | 55.9 (4) |
N1—C10—O1 | 113.0 (4) | F8i—F6—F5i | 96.3 (6) |
N1—C10—C9 | 125.4 (4) | B2—F6—F7i | 56.6 (4) |
O1—C10—C9 | 121.6 (4) | F8i—F6—F7i | 90.8 (5) |
N2—C11—O1 | 113.7 (4) | F5i—F6—F7i | 91.9 (5) |
N2—C11—S1 | 131.7 (4) | B2—F7—F6i | 52.8 (3) |
O1—C11—S1 | 114.5 (3) | B2—F7—F5i | 53.0 (4) |
C13—C12—S1 | 113.5 (4) | F6i—F7—F5i | 87.9 (5) |
C13—C12—H12A | 108.9 | B2—F7—F8i | 51.6 (3) |
S1—C12—H12A | 108.9 | F6i—F7—F8i | 87.0 (5) |
C13—C12—H12B | 108.9 | F5i—F7—F8i | 85.5 (5) |
S1—C12—H12B | 108.9 | B2—F8—F6i | 54.9 (4) |
H12A—C12—H12B | 107.7 | B2—F8—F5i | 54.4 (4) |
C12—C13—C14 | 113.9 (4) | F6i—F8—F5i | 92.6 (6) |
C12—C13—H13A | 108.8 | B2—F8—F7i | 52.2 (3) |
C14—C13—H13A | 108.8 | F6i—F8—F7i | 87.5 (5) |
C12—C13—H13B | 108.8 | F5i—F8—F7i | 86.0 (5) |
C14—C13—H13B | 108.8 | C10—N1—N2 | 106.9 (4) |
H13A—C13—H13B | 107.7 | C10—N1—Cu1iii | 107.1 (3) |
C15—C14—C13 | 110.1 (4) | N2—N1—Cu1iii | 145.5 (3) |
C15—C14—H14A | 109.6 | C11—N2—N1 | 104.9 (4) |
C13—C14—H14A | 109.6 | C9—N3—C1 | 117.3 (4) |
C15—C14—H14B | 109.6 | C9—N3—Cu1iii | 113.8 (3) |
C13—C14—H14B | 109.6 | C1—N3—Cu1iii | 128.7 (3) |
H14A—C14—H14B | 108.2 | C18—N4—C22 | 117.5 (4) |
C14—C15—S2 | 108.6 (4) | C18—N4—Cu1 | 113.8 (3) |
C14—C15—H15A | 110.0 | C22—N4—Cu1 | 128.6 (3) |
S2—C15—H15A | 110.0 | C17—N5—N6 | 107.0 (3) |
C14—C15—H15B | 110.0 | C17—N5—Cu1 | 109.9 (3) |
S2—C15—H15B | 110.0 | N6—N5—Cu1 | 143.0 (3) |
H15A—C15—H15B | 108.3 | C16—N6—N5 | 104.3 (4) |
N6—C16—O2 | 114.3 (4) | C10—O1—C11 | 101.5 (3) |
N6—C16—S2 | 128.4 (4) | C17—O2—C16 | 101.1 (3) |
O2—C16—S2 | 117.4 (3) | C28—O3—H3A | 109.7 |
N5—C17—O2 | 113.2 (4) | C11—S1—C12 | 98.8 (2) |
N5—C17—C18 | 123.7 (4) | C16—S2—C15 | 97.2 (2) |
N3—C1—C2—C3 | 179.0 (4) | F6i—B2—F7—F5i | −120.9 (5) |
C6—C1—C2—C3 | 0.6 (6) | F6—B2—F7—F5i | 59.1 (5) |
C1—C2—C3—C4 | 0.4 (7) | F5—B2—F7—F5i | 180.000 (4) |
C2—C3—C4—C5 | −0.9 (7) | F8i—B2—F7—F5i | 118.1 (6) |
C3—C4—C5—C6 | 0.4 (7) | F8—B2—F7—F5i | −61.9 (6) |
C4—C5—C6—C7 | −178.8 (4) | F7i—B2—F7—F5i | 33 (100) |
C4—C5—C6—C1 | 0.6 (6) | F6i—B2—F7—F8i | 121.1 (5) |
N3—C1—C6—C7 | 0.0 (6) | F6—B2—F7—F8i | −58.9 (5) |
C2—C1—C6—C7 | 178.3 (4) | F5—B2—F7—F8i | 61.9 (6) |
N3—C1—C6—C5 | −179.4 (4) | F5i—B2—F7—F8i | −118.1 (6) |
C2—C1—C6—C5 | −1.1 (6) | F8—B2—F7—F8i | 180.000 (4) |
C5—C6—C7—C8 | 179.7 (4) | F7i—B2—F7—F8i | −85 (100) |
C1—C6—C7—C8 | 0.3 (6) | F6—B2—F8—F6i | 180.000 (2) |
C6—C7—C8—C9 | −0.3 (6) | F5—B2—F8—F6i | 55.1 (6) |
C7—C8—C9—N3 | 0.2 (7) | F5i—B2—F8—F6i | −124.9 (6) |
C7—C8—C9—C10 | 180.0 (4) | F8i—B2—F8—F6i | −120 (100) |
N3—C9—C10—N1 | 6.2 (6) | F7i—B2—F8—F6i | 118.5 (6) |
C8—C9—C10—N1 | −173.6 (4) | F7—B2—F8—F6i | −61.5 (6) |
N3—C9—C10—O1 | −171.6 (4) | F6i—B2—F8—F5i | 124.9 (6) |
C8—C9—C10—O1 | 8.6 (6) | F6—B2—F8—F5i | −55.1 (6) |
S1—C12—C13—C14 | −61.6 (5) | F5—B2—F8—F5i | 180.000 (5) |
C12—C13—C14—C15 | −178.1 (4) | F8i—B2—F8—F5i | 5 (100) |
C13—C14—C15—S2 | −177.0 (4) | F7i—B2—F8—F5i | −116.5 (6) |
N5—C17—C18—N4 | −2.0 (6) | F7—B2—F8—F5i | 63.5 (6) |
O2—C17—C18—N4 | 177.8 (4) | F6i—B2—F8—F7i | −118.5 (6) |
N5—C17—C18—C19 | 178.0 (5) | F6—B2—F8—F7i | 61.5 (6) |
O2—C17—C18—C19 | −2.2 (7) | F5—B2—F8—F7i | −63.5 (6) |
N4—C18—C19—C20 | −2.3 (8) | F5i—B2—F8—F7i | 116.5 (6) |
C17—C18—C19—C20 | 177.7 (5) | F8i—B2—F8—F7i | 122 (100) |
C18—C19—C20—C21 | 1.6 (8) | F7—B2—F8—F7i | 180.000 (4) |
C19—C20—C21—C22 | 0.7 (8) | O1—C10—N1—N2 | −0.1 (5) |
C19—C20—C21—C26 | −179.9 (5) | C9—C10—N1—N2 | −178.2 (4) |
C20—C21—C22—N4 | −2.5 (7) | O1—C10—N1—Cu1iii | 173.8 (3) |
C26—C21—C22—N4 | 178.0 (4) | C9—C10—N1—Cu1iii | −4.2 (5) |
C20—C21—C22—C23 | 178.9 (5) | O1—C11—N2—N1 | 0.7 (5) |
C26—C21—C22—C23 | −0.6 (7) | S1—C11—N2—N1 | −178.5 (4) |
N4—C22—C23—C24 | −178.5 (5) | C10—N1—N2—C11 | −0.3 (5) |
C21—C22—C23—C24 | 0.1 (8) | Cu1iii—N1—N2—C11 | −170.0 (4) |
C22—C23—C24—C25 | 1.0 (8) | C8—C9—N3—C1 | 0.1 (6) |
C23—C24—C25—C26 | −1.7 (9) | C10—C9—N3—C1 | −179.7 (3) |
C24—C25—C26—C21 | 1.1 (9) | C8—C9—N3—Cu1iii | 175.3 (3) |
C20—C21—C26—C25 | −179.5 (6) | C10—C9—N3—Cu1iii | −4.5 (4) |
C22—C21—C26—C25 | 0.0 (8) | C2—C1—N3—C9 | −178.5 (4) |
Cl2—C27—Cl1—Cl1ii | −68 (3) | C6—C1—N3—C9 | −0.2 (5) |
F4—B1—F2—F2iv | −5.6 (15) | C2—C1—N3—Cu1iii | 7.1 (5) |
F1—B1—F2—F2iv | −125.3 (16) | C6—C1—N3—Cu1iii | −174.6 (3) |
F3—B1—F2—F2iv | 115.9 (11) | C19—C18—N4—C22 | 0.5 (7) |
F6—B2—F5—F6i | 180.000 (4) | C17—C18—N4—C22 | −179.6 (4) |
F5i—B2—F5—F6i | 139 (100) | C19—C18—N4—Cu1 | −175.9 (4) |
F8i—B2—F5—F6i | 126.3 (6) | C17—C18—N4—Cu1 | 4.0 (5) |
F8—B2—F5—F6i | −53.7 (6) | C23—C22—N4—C18 | −179.5 (4) |
F7i—B2—F5—F6i | −120.1 (5) | C21—C22—N4—C18 | 2.0 (6) |
F7—B2—F5—F6i | 59.9 (6) | C23—C22—N4—Cu1 | −3.7 (6) |
F6i—B2—F5—F8i | −126.3 (6) | C21—C22—N4—Cu1 | 177.7 (3) |
F6—B2—F5—F8i | 53.7 (6) | N5—Cu1—N4—C18 | −3.8 (3) |
F5i—B2—F5—F8i | 12 (100) | N3iii—Cu1—N4—C18 | 131.8 (3) |
F8—B2—F5—F8i | 180.000 (7) | N1iii—Cu1—N4—C18 | −125.2 (3) |
F7i—B2—F5—F8i | 113.5 (5) | N5—Cu1—N4—C22 | −179.7 (4) |
F7—B2—F5—F8i | −66.5 (5) | N3iii—Cu1—N4—C22 | −44.1 (4) |
F6i—B2—F5—F7i | 120.1 (5) | N1iii—Cu1—N4—C22 | 58.9 (4) |
F6—B2—F5—F7i | −59.9 (5) | O2—C17—N5—N6 | 0.3 (5) |
F5i—B2—F5—F7i | −101 (100) | C18—C17—N5—N6 | −179.9 (4) |
F8i—B2—F5—F7i | −113.5 (5) | O2—C17—N5—Cu1 | 179.0 (3) |
F8—B2—F5—F7i | 66.5 (5) | C18—C17—N5—Cu1 | −1.2 (5) |
F7—B2—F5—F7i | 180.000 (3) | N3iii—Cu1—N5—C17 | −121.0 (3) |
F6i—B2—F6—F8i | 97 (100) | N4—Cu1—N5—C17 | 2.6 (3) |
F5—B2—F6—F8i | −54.9 (7) | N1iii—Cu1—N5—C17 | 130.0 (3) |
F5i—B2—F6—F8i | 125.1 (7) | N3iii—Cu1—N5—N6 | 56.9 (5) |
F8—B2—F6—F8i | 180.000 (2) | N4—Cu1—N5—N6 | −179.5 (5) |
F7i—B2—F6—F8i | −115.3 (5) | N1iii—Cu1—N5—N6 | −52.1 (5) |
F7—B2—F6—F8i | 64.7 (5) | O2—C16—N6—N5 | −0.5 (5) |
F6i—B2—F6—F5i | −28 (100) | S2—C16—N6—N5 | 179.3 (4) |
F5—B2—F6—F5i | 180.000 (4) | C17—N5—N6—C16 | 0.1 (5) |
F8i—B2—F6—F5i | −125.1 (7) | Cu1—N5—N6—C16 | −177.8 (4) |
F8—B2—F6—F5i | 54.9 (7) | N1—C10—O1—C11 | 0.5 (5) |
F7i—B2—F6—F5i | 119.7 (6) | C9—C10—O1—C11 | 178.6 (4) |
F7—B2—F6—F5i | −60.3 (6) | N2—C11—O1—C10 | −0.8 (5) |
F6i—B2—F6—F7i | −148 (100) | S1—C11—O1—C10 | 178.5 (3) |
F5—B2—F6—F7i | 60.3 (6) | N5—C17—O2—C16 | −0.5 (5) |
F5i—B2—F6—F7i | −119.7 (6) | C18—C17—O2—C16 | 179.7 (4) |
F8i—B2—F6—F7i | 115.3 (5) | N6—C16—O2—C17 | 0.6 (5) |
F8—B2—F6—F7i | −64.7 (5) | S2—C16—O2—C17 | −179.2 (3) |
F7—B2—F6—F7i | 180.000 (2) | N2—C11—S1—C12 | −6.2 (5) |
F6—B2—F7—F6i | 180.000 (2) | O1—C11—S1—C12 | 174.7 (4) |
F5—B2—F7—F6i | −59.1 (5) | C13—C12—S1—C11 | −76.2 (4) |
F5i—B2—F7—F6i | 120.9 (5) | N6—C16—S2—C15 | −1.2 (5) |
F8i—B2—F7—F6i | −121.1 (5) | O2—C16—S2—C15 | 178.5 (4) |
F8—B2—F7—F6i | 58.9 (5) | C14—C15—S2—C16 | −176.1 (4) |
F7i—B2—F7—F6i | 154 (100) |
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+2, −y, −z+1; (iii) −x, −y+2, −z+1; (iv) −x+2, −y+1, −z. |
[Cu2(C26H20N6O2S2)2](ClO4)2·2CH2Cl2·CH4O | Z = 1 |
Mr = 1553.07 | F(000) = 790 |
Triclinic, P1 | Dx = 1.618 Mg m−3 |
a = 11.2499 (11) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 11.5798 (11) Å | Cell parameters from 1468 reflections |
c = 13.6976 (15) Å | θ = 3.6–21.5° |
α = 67.635 (10)° | µ = 1.12 mm−1 |
β = 81.106 (9)° | T = 100 K |
γ = 75.524 (8)° | Plate, yellow |
V = 1594.3 (3) Å3 | 0.16 × 0.10 × 0.02 mm |
Agilent SuperNova Dual Source diffractometer with an Eos detector | 6039 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3134 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.068 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 25.7°, θmin = 2.9° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −13→14 |
Tmin = 0.949, Tmax = 1.000 | l = −15→16 |
11239 measured reflections |
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)] = 0.086 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.251 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1066P)2] where P = (Fo2 + 2Fc2)/3 |
6039 reflections | (Δ/σ)max < 0.001 |
488 parameters | Δρmax = 1.08 e Å−3 |
17 restraints | Δρmin = −0.70 e Å−3 |
Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.6280 (7) | 0.9767 (7) | 0.3469 (6) | 0.046 (2) | |
C2 | 0.7198 (9) | 1.0121 (7) | 0.3798 (6) | 0.055 (2) | |
H2 | 0.8005 | 0.9662 | 0.3797 | 0.067* | |
C3 | 0.6914 (10) | 1.1146 (8) | 0.4124 (7) | 0.071 (3) | |
H3 | 0.7525 | 1.1358 | 0.4369 | 0.085* | |
C4 | 0.5705 (13) | 1.1881 (9) | 0.4093 (9) | 0.085 (4) | |
H4 | 0.5534 | 1.2608 | 0.4270 | 0.101* | |
C5 | 0.4812 (12) | 1.1535 (9) | 0.3811 (8) | 0.085 (4) | |
H5 | 0.4015 | 1.2012 | 0.3829 | 0.102* | |
C6 | 0.5013 (9) | 1.0467 (8) | 0.3481 (6) | 0.060 (3) | |
C7 | 0.4109 (9) | 1.0082 (9) | 0.3152 (8) | 0.070 (3) | |
H7 | 0.3298 | 1.0532 | 0.3142 | 0.084* | |
C8 | 0.4412 (7) | 0.9067 (8) | 0.2853 (6) | 0.056 (2) | |
H8 | 0.3815 | 0.8793 | 0.2648 | 0.067* | |
C9 | 0.5670 (6) | 0.8410 (7) | 0.2856 (6) | 0.0399 (18) | |
C10 | 0.6110 (6) | 0.7348 (7) | 0.2498 (6) | 0.0390 (18) | |
C11 | 0.6185 (7) | 0.5859 (7) | 0.1938 (6) | 0.0434 (19) | |
C12 | 0.7036 (7) | 0.3786 (8) | 0.1423 (7) | 0.053 (2) | |
H12A | 0.7646 | 0.4217 | 0.0936 | 0.063* | |
H12B | 0.7356 | 0.3379 | 0.2119 | 0.063* | |
C13 | 0.6778 (7) | 0.2789 (7) | 0.1062 (7) | 0.050 (2) | |
H13A | 0.6395 | 0.3210 | 0.0393 | 0.060* | |
H13B | 0.6208 | 0.2325 | 0.1577 | 0.060* | |
C14 | 0.7975 (7) | 0.1837 (8) | 0.0929 (6) | 0.048 (2) | |
H14A | 0.8521 | 0.2300 | 0.0383 | 0.057* | |
H14B | 0.8385 | 0.1466 | 0.1586 | 0.057* | |
C15 | 1.2239 (7) | 0.9225 (7) | −0.0640 (6) | 0.048 (2) | |
H15A | 1.1458 | 0.9810 | −0.0616 | 0.058* | |
H15B | 1.2773 | 0.9696 | −0.1193 | 0.058* | |
C16 | 1.1638 (7) | 0.8341 (7) | 0.1450 (6) | 0.0390 (18) | |
C17 | 1.0725 (6) | 0.7642 (6) | 0.2957 (6) | 0.0378 (18) | |
C18 | 1.0496 (6) | 0.7059 (6) | 0.4091 (6) | 0.0356 (17) | |
C19 | 1.1391 (6) | 0.6756 (6) | 0.4811 (6) | 0.0356 (17) | |
H19 | 1.2170 | 0.6931 | 0.4572 | 0.043* | |
C20 | 1.1096 (6) | 0.6205 (6) | 0.5860 (6) | 0.0385 (18) | |
H20 | 1.1677 | 0.6000 | 0.6348 | 0.046* | |
C21 | 0.9922 (7) | 0.5946 (6) | 0.6210 (6) | 0.0377 (18) | |
C22 | 0.9558 (7) | 0.5375 (7) | 0.7285 (6) | 0.045 (2) | |
H22 | 1.0109 | 0.5161 | 0.7798 | 0.054* | |
C23 | 0.8416 (7) | 0.5134 (7) | 0.7579 (6) | 0.048 (2) | |
H23 | 0.8192 | 0.4758 | 0.8294 | 0.058* | |
C24 | 0.7554 (7) | 0.5444 (7) | 0.6820 (7) | 0.050 (2) | |
H24 | 0.6776 | 0.5260 | 0.7036 | 0.060* | |
C25 | 0.7871 (6) | 0.6020 (7) | 0.5758 (7) | 0.0413 (19) | |
H25 | 0.7298 | 0.6243 | 0.5261 | 0.050* | |
C26 | 0.9061 (6) | 0.6273 (6) | 0.5424 (6) | 0.0372 (18) | |
C27 | 0.1362 (12) | 0.2382 (16) | 0.039 (3) | 0.145 (6) | 0.630 (6) |
H27A | 0.1196 | 0.2134 | −0.0171 | 0.174* | 0.630 (6) |
H27B | 0.1052 | 0.1808 | 0.1047 | 0.174* | 0.630 (6) |
C28 | 0.066 (3) | 0.116 (3) | 0.287 (3) | 0.123 (13) | 0.50 |
H28A | −0.0200 | 0.1559 | 0.2868 | 0.185* | 0.50 |
H28B | 0.0964 | 0.1202 | 0.2164 | 0.185* | 0.50 |
H28C | 0.1106 | 0.1587 | 0.3114 | 0.185* | 0.50 |
Cl1 | 0.0450 (4) | 0.0756 (7) | 0.3597 (5) | 0.0512 (13) | 0.50 |
Cl2 | 0.5000 | 0.5000 | 0.5000 | 0.0448 (7) | |
Cl3 | 0.2924 (6) | 0.2066 (7) | 0.0425 (5) | 0.154 (3) | 0.630 (6) |
Cl4 | 0.0483 (5) | 0.3867 (6) | 0.0207 (4) | 0.114 (2) | 0.630 (6) |
C27' | 0.186 (2) | 0.234 (4) | 0.1104 (15) | 0.145 (6) | 0.370 (6) |
H27C | 0.1293 | 0.2915 | 0.1412 | 0.174* | 0.370 (6) |
H27D | 0.1955 | 0.1485 | 0.1628 | 0.174* | 0.370 (6) |
Cl3' | 0.3244 (12) | 0.2776 (12) | 0.0791 (9) | 0.161 (4) | 0.370 (6) |
Cl4' | 0.1245 (11) | 0.2386 (14) | 0.0009 (10) | 0.136 (4) | 0.370 (6) |
Cu1 | 0.82680 (7) | 0.75212 (8) | 0.31192 (7) | 0.0409 (3) | |
N1 | 0.7250 (5) | 0.6744 (5) | 0.2502 (5) | 0.0370 (15) | |
N2 | 0.7308 (5) | 0.5751 (6) | 0.2122 (5) | 0.0434 (16) | |
N3 | 0.6580 (5) | 0.8743 (5) | 0.3147 (4) | 0.0373 (15) | |
N4 | 0.9354 (5) | 0.6829 (5) | 0.4375 (5) | 0.0320 (14) | |
N5 | 0.9904 (5) | 0.8031 (5) | 0.2275 (5) | 0.0382 (15) | |
N6 | 1.0508 (5) | 0.8484 (6) | 0.1277 (5) | 0.0421 (15) | |
O2 | 0.5374 (4) | 0.6848 (5) | 0.2138 (4) | 0.0453 (14) | |
O3 | 1.1857 (4) | 0.7785 (4) | 0.2503 (4) | 0.0393 (12) | |
O4 | 0.1237 (10) | 0.1271 (10) | 0.3936 (11) | 0.067 (4) | 0.50 |
O5 | −0.0137 (12) | −0.0094 (13) | 0.4502 (11) | 0.078 (4) | 0.50 |
O6 | −0.0466 (10) | 0.1727 (10) | 0.2964 (9) | 0.054 (3) | 0.50 |
O7 | 0.1137 (19) | 0.003 (2) | 0.2983 (19) | 0.071 (6) | 0.50 |
O8 | 0.5976 (11) | 0.4737 (16) | 0.4306 (12) | 0.100 (6) | 0.50 |
O9 | 0.547 (2) | 0.502 (3) | 0.5845 (14) | 0.158 (9) | 0.50 |
O10 | 0.4399 (18) | 0.4042 (16) | 0.5362 (12) | 0.103 (6) | 0.50 |
O11 | 0.4313 (16) | 0.6181 (14) | 0.4412 (15) | 0.122 (7) | 0.50 |
O1M | 0.080 (3) | −0.006 (3) | 0.3509 (19) | 0.115 (10) | 0.50 |
H1M | 0.0877 | −0.0512 | 0.3152 | 0.172* | 0.50 |
S1 | 0.56145 (18) | 0.4933 (2) | 0.14653 (18) | 0.0543 (6) | |
S2 | 1.29163 (18) | 0.8690 (2) | 0.06107 (17) | 0.0533 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.060 (5) | 0.027 (4) | 0.035 (5) | 0.003 (4) | −0.003 (4) | −0.002 (3) |
C2 | 0.086 (7) | 0.033 (4) | 0.048 (5) | −0.009 (4) | 0.006 (5) | −0.019 (4) |
C3 | 0.118 (9) | 0.042 (5) | 0.054 (6) | −0.022 (6) | 0.010 (5) | −0.022 (4) |
C4 | 0.146 (12) | 0.024 (5) | 0.064 (7) | 0.005 (6) | 0.006 (7) | −0.014 (4) |
C5 | 0.121 (10) | 0.045 (6) | 0.053 (7) | 0.022 (6) | 0.017 (6) | −0.010 (5) |
C6 | 0.077 (7) | 0.038 (5) | 0.037 (5) | 0.022 (5) | 0.007 (4) | −0.007 (4) |
C7 | 0.053 (6) | 0.059 (6) | 0.068 (7) | 0.023 (5) | −0.010 (5) | −0.010 (5) |
C8 | 0.027 (4) | 0.064 (6) | 0.052 (6) | 0.015 (4) | −0.009 (4) | −0.008 (4) |
C9 | 0.038 (4) | 0.039 (4) | 0.034 (4) | 0.005 (4) | −0.004 (3) | −0.012 (3) |
C10 | 0.033 (4) | 0.046 (4) | 0.035 (4) | −0.008 (4) | −0.011 (3) | −0.009 (3) |
C11 | 0.038 (4) | 0.046 (5) | 0.046 (5) | −0.009 (4) | −0.008 (4) | −0.014 (4) |
C12 | 0.048 (5) | 0.063 (5) | 0.055 (6) | −0.012 (4) | −0.009 (4) | −0.028 (4) |
C13 | 0.045 (5) | 0.055 (5) | 0.049 (5) | −0.016 (4) | −0.007 (4) | −0.010 (4) |
C14 | 0.040 (4) | 0.062 (5) | 0.039 (5) | −0.010 (4) | −0.009 (4) | −0.014 (4) |
C15 | 0.056 (5) | 0.049 (5) | 0.038 (5) | −0.011 (4) | −0.010 (4) | −0.012 (4) |
C16 | 0.043 (4) | 0.040 (4) | 0.036 (5) | 0.000 (4) | −0.010 (4) | −0.018 (3) |
C17 | 0.036 (4) | 0.031 (4) | 0.050 (5) | −0.001 (3) | −0.006 (4) | −0.020 (3) |
C18 | 0.032 (4) | 0.030 (4) | 0.047 (5) | 0.003 (3) | −0.010 (3) | −0.020 (3) |
C19 | 0.025 (4) | 0.035 (4) | 0.047 (5) | 0.000 (3) | −0.005 (3) | −0.018 (3) |
C20 | 0.034 (4) | 0.041 (4) | 0.044 (5) | 0.001 (4) | −0.011 (3) | −0.022 (4) |
C21 | 0.047 (5) | 0.024 (4) | 0.042 (5) | 0.001 (3) | −0.006 (4) | −0.016 (3) |
C22 | 0.043 (5) | 0.039 (4) | 0.051 (5) | 0.005 (4) | −0.012 (4) | −0.019 (4) |
C23 | 0.048 (5) | 0.043 (5) | 0.045 (5) | 0.008 (4) | −0.007 (4) | −0.017 (4) |
C24 | 0.039 (5) | 0.047 (5) | 0.064 (6) | −0.001 (4) | 0.006 (4) | −0.027 (4) |
C25 | 0.034 (4) | 0.034 (4) | 0.054 (5) | 0.007 (3) | −0.009 (4) | −0.020 (4) |
C26 | 0.033 (4) | 0.026 (4) | 0.052 (5) | 0.002 (3) | −0.005 (4) | −0.017 (3) |
C27 | 0.134 (8) | 0.204 (9) | 0.109 (12) | −0.063 (7) | −0.017 (7) | −0.049 (8) |
C28 | 0.07 (2) | 0.13 (3) | 0.14 (3) | −0.01 (2) | 0.00 (2) | −0.03 (3) |
Cl1 | 0.048 (3) | 0.047 (3) | 0.073 (4) | −0.011 (3) | −0.006 (3) | −0.036 (3) |
Cl2 | 0.0365 (15) | 0.0434 (16) | 0.060 (2) | −0.0084 (14) | 0.0004 (14) | −0.0260 (14) |
Cl3 | 0.175 (5) | 0.158 (6) | 0.110 (4) | −0.106 (4) | −0.069 (4) | 0.039 (4) |
Cl4 | 0.131 (5) | 0.169 (6) | 0.070 (3) | −0.083 (4) | 0.026 (3) | −0.052 (3) |
C27' | 0.134 (8) | 0.204 (9) | 0.109 (12) | −0.063 (7) | −0.017 (7) | −0.049 (8) |
Cl3' | 0.186 (6) | 0.158 (7) | 0.117 (6) | −0.096 (5) | −0.058 (5) | 0.031 (5) |
Cl4' | 0.129 (7) | 0.197 (9) | 0.104 (10) | −0.065 (6) | −0.018 (6) | −0.056 (7) |
Cu1 | 0.0297 (5) | 0.0432 (6) | 0.0517 (7) | 0.0010 (4) | −0.0122 (4) | −0.0208 (5) |
N1 | 0.030 (3) | 0.034 (3) | 0.048 (4) | 0.001 (3) | −0.014 (3) | −0.017 (3) |
N2 | 0.037 (4) | 0.049 (4) | 0.051 (4) | −0.001 (3) | −0.010 (3) | −0.028 (3) |
N3 | 0.039 (3) | 0.032 (3) | 0.035 (4) | 0.001 (3) | −0.005 (3) | −0.009 (3) |
N4 | 0.027 (3) | 0.026 (3) | 0.043 (4) | 0.004 (3) | −0.007 (3) | −0.015 (3) |
N5 | 0.039 (3) | 0.033 (3) | 0.040 (4) | −0.009 (3) | −0.006 (3) | −0.009 (3) |
N6 | 0.039 (4) | 0.047 (4) | 0.041 (4) | −0.007 (3) | −0.003 (3) | −0.018 (3) |
O2 | 0.030 (3) | 0.047 (3) | 0.060 (4) | −0.004 (2) | −0.020 (2) | −0.015 (3) |
O3 | 0.032 (3) | 0.041 (3) | 0.045 (3) | −0.008 (2) | −0.005 (2) | −0.014 (2) |
O4 | 0.053 (7) | 0.045 (6) | 0.114 (11) | 0.009 (6) | −0.034 (7) | −0.042 (7) |
O5 | 0.065 (8) | 0.080 (9) | 0.083 (12) | −0.005 (7) | −0.022 (8) | −0.022 (9) |
O6 | 0.054 (7) | 0.051 (7) | 0.056 (8) | −0.004 (6) | −0.026 (6) | −0.014 (6) |
O7 | 0.081 (11) | 0.067 (13) | 0.092 (17) | −0.021 (9) | 0.008 (11) | −0.060 (14) |
O8 | 0.038 (7) | 0.109 (12) | 0.092 (12) | 0.025 (8) | 0.017 (7) | −0.003 (9) |
O9 | 0.26 (3) | 0.22 (2) | 0.078 (14) | −0.17 (2) | −0.007 (14) | −0.068 (14) |
O10 | 0.145 (15) | 0.096 (11) | 0.076 (11) | −0.088 (12) | −0.046 (10) | 0.013 (9) |
O11 | 0.087 (12) | 0.067 (10) | 0.125 (15) | 0.034 (9) | 0.033 (10) | 0.013 (10) |
O1M | 0.21 (3) | 0.071 (16) | 0.08 (2) | −0.036 (17) | −0.017 (17) | −0.037 (15) |
S1 | 0.0433 (12) | 0.0646 (14) | 0.0649 (15) | −0.0132 (11) | −0.0180 (10) | −0.0274 (11) |
S2 | 0.0460 (12) | 0.0725 (15) | 0.0473 (14) | −0.0215 (11) | −0.0024 (10) | −0.0225 (11) |
C1—N3 | 1.367 (9) | C23—H23 | 0.9300 |
C1—C2 | 1.391 (11) | C24—C25 | 1.381 (11) |
C1—C6 | 1.454 (11) | C24—H24 | 0.9300 |
C2—C3 | 1.370 (11) | C25—C26 | 1.412 (10) |
C2—H2 | 0.9300 | C25—H25 | 0.9300 |
C3—C4 | 1.410 (14) | C26—N4 | 1.357 (9) |
C3—H3 | 0.9300 | C27—Cl4 | 1.703 (10) |
C4—C5 | 1.325 (15) | C27—Cl3 | 1.708 (10) |
C4—H4 | 0.9300 | C27—H27A | 0.9700 |
C5—C6 | 1.428 (14) | C27—H27B | 0.9700 |
C5—H5 | 0.9300 | C28—O1M | 1.33 (4) |
C6—C7 | 1.398 (13) | C28—H28A | 0.9600 |
C7—C8 | 1.338 (13) | C28—H28B | 0.9600 |
C7—H7 | 0.9300 | C28—H28C | 0.9600 |
C8—C9 | 1.429 (9) | Cl1—O4 | 1.399 (12) |
C8—H8 | 0.9300 | Cl1—O7 | 1.421 (9) |
C9—N3 | 1.340 (9) | Cl1—O6 | 1.426 (12) |
C9—C10 | 1.441 (10) | Cl1—O5 | 1.444 (16) |
C10—N1 | 1.297 (8) | Cl1—H1M | 1.7303 |
C10—O2 | 1.359 (8) | Cl2—O10 | 1.336 (13) |
C11—N2 | 1.293 (8) | Cl2—O10ii | 1.336 (13) |
C11—O2 | 1.363 (9) | Cl2—O9 | 1.352 (15) |
C11—S1 | 1.727 (8) | Cl2—O9ii | 1.352 (15) |
C12—C13 | 1.520 (11) | Cl2—O8ii | 1.390 (13) |
C12—S1 | 1.814 (8) | Cl2—O8 | 1.390 (13) |
C12—H12A | 0.9700 | Cl2—O11 | 1.394 (12) |
C12—H12B | 0.9700 | Cl2—O11ii | 1.394 (13) |
C13—C14 | 1.548 (11) | Cl4—Cl4iii | 2.453 (14) |
C13—H13A | 0.9700 | C27'—Cl3' | 1.699 (10) |
C13—H13B | 0.9700 | C27'—Cl4' | 1.724 (10) |
C14—C15i | 1.509 (10) | C27'—H27C | 0.9700 |
C14—H14A | 0.9700 | C27'—H27D | 0.9700 |
C14—H14B | 0.9700 | Cu1—N4 | 2.051 (5) |
C15—C14i | 1.509 (10) | Cu1—N1 | 2.057 (6) |
C15—S2 | 1.806 (7) | Cu1—N3 | 2.070 (5) |
C15—H15A | 0.9700 | Cu1—N5 | 2.106 (6) |
C15—H15B | 0.9700 | N1—N2 | 1.416 (8) |
C16—N6 | 1.287 (8) | N5—N6 | 1.398 (8) |
C16—O3 | 1.371 (8) | O5—O5iv | 1.55 (3) |
C16—S2 | 1.726 (8) | O7—H1M | 0.7036 |
C17—N5 | 1.291 (8) | O8—O10ii | 1.59 (2) |
C17—O3 | 1.348 (8) | O8—O9ii | 1.61 (2) |
C17—C18 | 1.449 (10) | O8—O11ii | 1.70 (2) |
C18—N4 | 1.345 (8) | O9—O11ii | 1.51 (3) |
C18—C19 | 1.406 (9) | O9—O10ii | 1.61 (2) |
C19—C20 | 1.358 (10) | O9—O8ii | 1.61 (2) |
C19—H19 | 0.9300 | O10—O11ii | 1.47 (2) |
C20—C21 | 1.399 (9) | O10—O8ii | 1.59 (2) |
C20—H20 | 0.9300 | O10—O9ii | 1.61 (2) |
C21—C22 | 1.408 (10) | O11—O10ii | 1.47 (2) |
C21—C26 | 1.439 (10) | O11—O9ii | 1.51 (3) |
C22—C23 | 1.350 (10) | O11—O8ii | 1.70 (2) |
C22—H22 | 0.9300 | O1M—H1M | 0.8200 |
C23—C24 | 1.416 (10) | ||
N3—C1—C2 | 119.2 (7) | O1M—C28—H28C | 109.5 |
N3—C1—C6 | 120.3 (8) | H28A—C28—H28C | 109.5 |
C2—C1—C6 | 120.5 (8) | H28B—C28—H28C | 109.5 |
C3—C2—C1 | 120.0 (9) | O4—Cl1—O7 | 109.9 (11) |
C3—C2—H2 | 120.0 | O4—Cl1—O6 | 111.8 (7) |
C1—C2—H2 | 120.0 | O7—Cl1—O6 | 108.1 (14) |
C2—C3—C4 | 120.8 (10) | O4—Cl1—O5 | 109.8 (9) |
C2—C3—H3 | 119.6 | O7—Cl1—O5 | 107.8 (13) |
C4—C3—H3 | 119.6 | O6—Cl1—O5 | 109.5 (7) |
C5—C4—C3 | 120.0 (10) | O4—Cl1—H1M | 126.3 |
C5—C4—H4 | 120.0 | O7—Cl1—H1M | 23.2 |
C3—C4—H4 | 120.0 | O6—Cl1—H1M | 110.1 |
C4—C5—C6 | 123.2 (11) | O5—Cl1—H1M | 85.7 |
C4—C5—H5 | 118.4 | O10—Cl2—O10ii | 180.000 (3) |
C6—C5—H5 | 118.4 | O10—Cl2—O9 | 106.7 (10) |
C7—C6—C5 | 125.5 (10) | O10ii—Cl2—O9 | 73.3 (10) |
C7—C6—C1 | 119.1 (8) | O10—Cl2—O9ii | 73.3 (10) |
C5—C6—C1 | 115.4 (10) | O10ii—Cl2—O9ii | 106.7 (10) |
C8—C7—C6 | 120.0 (8) | O9—Cl2—O9ii | 180.000 (4) |
C8—C7—H7 | 120.0 | O10—Cl2—O8ii | 71.1 (10) |
C6—C7—H7 | 120.0 | O10ii—Cl2—O8ii | 108.9 (10) |
C7—C8—C9 | 118.8 (9) | O9—Cl2—O8ii | 71.9 (12) |
C7—C8—H8 | 120.6 | O9ii—Cl2—O8ii | 108.1 (12) |
C9—C8—H8 | 120.6 | O10—Cl2—O8 | 108.9 (10) |
N3—C9—C8 | 124.0 (7) | O10ii—Cl2—O8 | 71.1 (10) |
N3—C9—C10 | 112.4 (6) | O9—Cl2—O8 | 108.1 (12) |
C8—C9—C10 | 123.5 (7) | O9ii—Cl2—O8 | 71.9 (12) |
N1—C10—O2 | 112.3 (7) | O8ii—Cl2—O8 | 180.000 (3) |
N1—C10—C9 | 123.9 (6) | O10—Cl2—O11 | 115.1 (9) |
O2—C10—C9 | 123.8 (6) | O10ii—Cl2—O11 | 64.9 (9) |
N2—C11—O2 | 114.2 (7) | O9—Cl2—O11 | 113.3 (13) |
N2—C11—S1 | 128.3 (6) | O9ii—Cl2—O11 | 66.7 (13) |
O2—C11—S1 | 117.6 (5) | O8ii—Cl2—O11 | 75.4 (8) |
C13—C12—S1 | 108.8 (5) | O8—Cl2—O11 | 104.6 (8) |
C13—C12—H12A | 109.9 | O10—Cl2—O11ii | 64.9 (9) |
S1—C12—H12A | 109.9 | O10ii—Cl2—O11ii | 115.1 (9) |
C13—C12—H12B | 109.9 | O9—Cl2—O11ii | 66.7 (13) |
S1—C12—H12B | 109.9 | O9ii—Cl2—O11ii | 113.3 (13) |
H12A—C12—H12B | 108.3 | O8ii—Cl2—O11ii | 104.6 (8) |
C12—C13—C14 | 111.3 (6) | O8—Cl2—O11ii | 75.4 (8) |
C12—C13—H13A | 109.4 | O11—Cl2—O11ii | 180.0 (16) |
C14—C13—H13A | 109.4 | C27—Cl4—Cl4iii | 170.7 (9) |
C12—C13—H13B | 109.4 | Cl3'—C27'—Cl4' | 111.7 (12) |
C14—C13—H13B | 109.4 | Cl3'—C27'—H27C | 109.3 |
H13A—C13—H13B | 108.0 | Cl4'—C27'—H27C | 109.3 |
C15i—C14—C13 | 113.5 (6) | Cl3'—C27'—H27D | 109.3 |
C15i—C14—H14A | 108.9 | Cl4'—C27'—H27D | 109.3 |
C13—C14—H14A | 108.9 | H27C—C27'—H27D | 107.9 |
C15i—C14—H14B | 108.9 | N4—Cu1—N1 | 134.8 (2) |
C13—C14—H14B | 108.9 | N4—Cu1—N3 | 120.6 (2) |
H14A—C14—H14B | 107.7 | N1—Cu1—N3 | 81.0 (2) |
C14i—C15—S2 | 114.2 (5) | N4—Cu1—N5 | 81.9 (2) |
C14i—C15—H15A | 108.7 | N1—Cu1—N5 | 118.6 (2) |
S2—C15—H15A | 108.7 | N3—Cu1—N5 | 126.6 (2) |
C14i—C15—H15B | 108.7 | C10—N1—N2 | 107.0 (5) |
S2—C15—H15B | 108.7 | C10—N1—Cu1 | 109.2 (5) |
H15A—C15—H15B | 107.6 | N2—N1—Cu1 | 143.7 (4) |
N6—C16—O3 | 113.0 (6) | C11—N2—N1 | 104.4 (6) |
N6—C16—S2 | 132.2 (6) | C9—N3—C1 | 117.7 (6) |
O3—C16—S2 | 114.7 (5) | C9—N3—Cu1 | 113.3 (5) |
N5—C17—O3 | 112.9 (7) | C1—N3—Cu1 | 128.9 (5) |
N5—C17—C18 | 124.8 (7) | C18—N4—C26 | 117.3 (6) |
O3—C17—C18 | 122.3 (6) | C18—N4—Cu1 | 112.8 (5) |
N4—C18—C19 | 124.0 (7) | C26—N4—Cu1 | 129.7 (4) |
N4—C18—C17 | 113.2 (6) | C17—N5—N6 | 106.6 (6) |
C19—C18—C17 | 122.8 (7) | C17—N5—Cu1 | 107.0 (5) |
C20—C19—C18 | 118.7 (7) | N6—N5—Cu1 | 145.8 (4) |
C20—C19—H19 | 120.6 | C16—N6—N5 | 105.5 (6) |
C18—C19—H19 | 120.6 | C10—O2—C11 | 102.1 (5) |
C19—C20—C21 | 120.2 (6) | C17—O3—C16 | 101.9 (5) |
C19—C20—H20 | 119.9 | Cl1—O5—O5iv | 107.5 (13) |
C21—C20—H20 | 119.9 | Cl1—O7—H1M | 103.9 |
C20—C21—C22 | 123.1 (7) | Cl2—O8—O10ii | 52.9 (8) |
C20—C21—C26 | 117.8 (7) | Cl2—O8—O9ii | 53.0 (7) |
C22—C21—C26 | 119.2 (7) | O10ii—O8—O9ii | 84.9 (11) |
C23—C22—C21 | 120.7 (7) | Cl2—O8—O11ii | 52.4 (6) |
C23—C22—H22 | 119.7 | O10ii—O8—O11ii | 88.9 (11) |
C21—C22—H22 | 119.7 | O9ii—O8—O11ii | 87.6 (11) |
C22—C23—C24 | 121.2 (8) | Cl2—O9—O11ii | 58.0 (9) |
C22—C23—H23 | 119.4 | Cl2—O9—O10ii | 52.9 (8) |
C24—C23—H23 | 119.4 | O11ii—O9—O10ii | 95.3 (13) |
C25—C24—C23 | 119.9 (7) | Cl2—O9—O8ii | 55.2 (9) |
C25—C24—H24 | 120.1 | O11ii—O9—O8ii | 89.8 (12) |
C23—C24—H24 | 120.1 | O10ii—O9—O8ii | 87.2 (13) |
C24—C25—C26 | 120.3 (7) | Cl2—O10—O11ii | 59.4 (8) |
C24—C25—H25 | 119.9 | Cl2—O10—O8ii | 56.0 (7) |
C26—C25—H25 | 119.9 | O11ii—O10—O8ii | 92.3 (11) |
N4—C26—C25 | 119.2 (6) | Cl2—O10—O9ii | 53.8 (7) |
N4—C26—C21 | 122.1 (6) | O11ii—O10—O9ii | 96.5 (14) |
C25—C26—C21 | 118.8 (7) | O8ii—O10—O9ii | 88.2 (12) |
Cl4—C27—Cl3 | 122.0 (11) | Cl2—O11—O10ii | 55.6 (8) |
Cl4—C27—H27A | 106.8 | Cl2—O11—O9ii | 55.3 (9) |
Cl3—C27—H27A | 106.8 | O10ii—O11—O9ii | 92.8 (13) |
Cl4—C27—H27B | 106.8 | Cl2—O11—O8ii | 52.2 (6) |
Cl3—C27—H27B | 106.8 | O10ii—O11—O8ii | 88.5 (12) |
H27A—C27—H27B | 106.7 | O9ii—O11—O8ii | 87.2 (12) |
O1M—C28—H28A | 109.5 | C28—O1M—H1M | 109.0 |
O1M—C28—H28B | 109.5 | C11—S1—C12 | 97.6 (4) |
H28A—C28—H28B | 109.5 | C16—S2—C15 | 99.0 (4) |
N3—C1—C2—C3 | −180.0 (7) | N3—Cu1—N5—N6 | −67.8 (9) |
C6—C1—C2—C3 | −0.8 (12) | O3—C16—N6—N5 | 1.7 (8) |
C1—C2—C3—C4 | −2.4 (13) | S2—C16—N6—N5 | −179.6 (6) |
C2—C3—C4—C5 | 4.4 (15) | C17—N5—N6—C16 | −0.8 (7) |
C3—C4—C5—C6 | −3.0 (17) | Cu1—N5—N6—C16 | −169.8 (6) |
C4—C5—C6—C7 | −178.4 (11) | N1—C10—O2—C11 | 0.9 (8) |
C4—C5—C6—C1 | −0.1 (14) | C9—C10—O2—C11 | −177.8 (7) |
N3—C1—C6—C7 | −0.3 (11) | N2—C11—O2—C10 | −1.3 (8) |
C2—C1—C6—C7 | −179.5 (8) | S1—C11—O2—C10 | 179.5 (5) |
N3—C1—C6—C5 | −178.8 (7) | N5—C17—O3—C16 | 1.3 (7) |
C2—C1—C6—C5 | 2.0 (11) | C18—C17—O3—C16 | 178.9 (6) |
C5—C6—C7—C8 | 179.6 (8) | N6—C16—O3—C17 | −1.9 (8) |
C1—C6—C7—C8 | 1.3 (13) | S2—C16—O3—C17 | 179.2 (5) |
C6—C7—C8—C9 | −1.3 (13) | O4—Cl1—O5—O5iv | 10.8 (15) |
C7—C8—C9—N3 | 0.4 (12) | O7—Cl1—O5—O5iv | 130.4 (16) |
C7—C8—C9—C10 | −176.7 (8) | O6—Cl1—O5—O5iv | −112.2 (12) |
N3—C9—C10—N1 | 2.9 (10) | O10—Cl2—O8—O10ii | 180.000 (2) |
C8—C9—C10—N1 | −179.7 (7) | O9—Cl2—O8—O10ii | −64.5 (12) |
N3—C9—C10—O2 | −178.5 (6) | O9ii—Cl2—O8—O10ii | 115.5 (12) |
C8—C9—C10—O2 | −1.1 (11) | O8ii—Cl2—O8—O10ii | 159 (100) |
S1—C12—C13—C14 | 175.8 (5) | O11—Cl2—O8—O10ii | 56.5 (11) |
C12—C13—C14—C15i | 176.2 (6) | O11ii—Cl2—O8—O10ii | −123.5 (11) |
N5—C17—C18—N4 | 6.7 (10) | O10—Cl2—O8—O9ii | 64.5 (12) |
O3—C17—C18—N4 | −170.6 (6) | O10ii—Cl2—O8—O9ii | −115.5 (12) |
N5—C17—C18—C19 | −174.0 (7) | O9—Cl2—O8—O9ii | 180.000 (2) |
O3—C17—C18—C19 | 8.7 (10) | O8ii—Cl2—O8—O9ii | 43 (100) |
N4—C18—C19—C20 | −0.4 (10) | O11—Cl2—O8—O9ii | −59.0 (13) |
C17—C18—C19—C20 | −179.7 (6) | O11ii—Cl2—O8—O9ii | 121.0 (13) |
C18—C19—C20—C21 | 0.1 (10) | O10—Cl2—O8—O11ii | −56.5 (11) |
C19—C20—C21—C22 | 179.9 (6) | O10ii—Cl2—O8—O11ii | 123.5 (11) |
C19—C20—C21—C26 | 0.5 (10) | O9—Cl2—O8—O11ii | 59.0 (13) |
C20—C21—C22—C23 | −179.4 (7) | O9ii—Cl2—O8—O11ii | −121.0 (13) |
C26—C21—C22—C23 | 0.0 (10) | O8ii—Cl2—O8—O11ii | −78 (100) |
C21—C22—C23—C24 | 0.2 (11) | O11—Cl2—O8—O11ii | 180.000 (4) |
C22—C23—C24—C25 | −1.0 (11) | O10—Cl2—O9—O11ii | 52.4 (13) |
C23—C24—C25—C26 | 1.6 (11) | O10ii—Cl2—O9—O11ii | −127.6 (13) |
C24—C25—C26—N4 | 179.4 (6) | O9ii—Cl2—O9—O11ii | −37 (100) |
C24—C25—C26—C21 | −1.4 (10) | O8ii—Cl2—O9—O11ii | 115.4 (11) |
C20—C21—C26—N4 | −0.8 (10) | O8—Cl2—O9—O11ii | −64.6 (11) |
C22—C21—C26—N4 | 179.8 (6) | O11—Cl2—O9—O11ii | 180.000 (4) |
C20—C21—C26—C25 | 180.0 (6) | O10—Cl2—O9—O10ii | 180.000 (3) |
C22—C21—C26—C25 | 0.6 (9) | O9ii—Cl2—O9—O10ii | 91 (100) |
Cl3—C27—Cl4—Cl4iii | 28 (9) | O8ii—Cl2—O9—O10ii | −117.0 (12) |
O2—C10—N1—N2 | −0.2 (8) | O8—Cl2—O9—O10ii | 63.0 (12) |
C9—C10—N1—N2 | 178.5 (7) | O11—Cl2—O9—O10ii | −52.4 (13) |
O2—C10—N1—Cu1 | −177.5 (5) | O11ii—Cl2—O9—O10ii | 127.6 (13) |
C9—C10—N1—Cu1 | 1.2 (9) | O10—Cl2—O9—O8ii | −63.0 (12) |
N4—Cu1—N1—C10 | 121.5 (5) | O10ii—Cl2—O9—O8ii | 117.0 (12) |
N3—Cu1—N1—C10 | −3.1 (5) | O9ii—Cl2—O9—O8ii | −152 (100) |
N5—Cu1—N1—C10 | −130.0 (5) | O8—Cl2—O9—O8ii | 180.000 (2) |
N4—Cu1—N1—N2 | −54.1 (9) | O11—Cl2—O9—O8ii | 64.6 (11) |
N3—Cu1—N1—N2 | −178.8 (8) | O11ii—Cl2—O9—O8ii | −115.4 (11) |
N5—Cu1—N1—N2 | 54.3 (8) | O10ii—Cl2—O10—O11ii | 87 (100) |
O2—C11—N2—N1 | 1.2 (8) | O9—Cl2—O10—O11ii | −53.5 (15) |
S1—C11—N2—N1 | −179.7 (6) | O9ii—Cl2—O10—O11ii | 126.5 (15) |
C10—N1—N2—C11 | −0.6 (8) | O8ii—Cl2—O10—O11ii | −117.0 (12) |
Cu1—N1—N2—C11 | 175.1 (6) | O8—Cl2—O10—O11ii | 63.0 (12) |
C8—C9—N3—C1 | 0.5 (11) | O11—Cl2—O10—O11ii | 180.000 (2) |
C10—C9—N3—C1 | 177.9 (6) | O10ii—Cl2—O10—O8ii | −156 (100) |
C8—C9—N3—Cu1 | 177.2 (6) | O9—Cl2—O10—O8ii | 63.5 (14) |
C10—C9—N3—Cu1 | −5.4 (8) | O9ii—Cl2—O10—O8ii | −116.5 (14) |
C2—C1—N3—C9 | 178.7 (7) | O8—Cl2—O10—O8ii | 180.000 (2) |
C6—C1—N3—C9 | −0.5 (10) | O11—Cl2—O10—O8ii | −63.0 (12) |
C2—C1—N3—Cu1 | 2.6 (10) | O11ii—Cl2—O10—O8ii | 117.0 (12) |
C6—C1—N3—Cu1 | −176.6 (5) | O10ii—Cl2—O10—O9ii | −40 (100) |
N4—Cu1—N3—C9 | −132.5 (5) | O9—Cl2—O10—O9ii | 180.000 (4) |
N1—Cu1—N3—C9 | 4.9 (5) | O8ii—Cl2—O10—O9ii | 116.5 (14) |
N5—Cu1—N3—C9 | 124.0 (5) | O8—Cl2—O10—O9ii | −63.5 (14) |
N4—Cu1—N3—C1 | 43.7 (7) | O11—Cl2—O10—O9ii | 53.5 (15) |
N1—Cu1—N3—C1 | −178.9 (6) | O11ii—Cl2—O10—O9ii | −126.5 (15) |
N5—Cu1—N3—C1 | −59.8 (7) | O10—Cl2—O11—O10ii | 180.000 (2) |
C19—C18—N4—C26 | 0.1 (9) | O9—Cl2—O11—O10ii | 56.9 (14) |
C17—C18—N4—C26 | 179.4 (6) | O9ii—Cl2—O11—O10ii | −123.1 (14) |
C19—C18—N4—Cu1 | 175.7 (5) | O8ii—Cl2—O11—O10ii | 119.4 (13) |
C17—C18—N4—Cu1 | −5.0 (7) | O8—Cl2—O11—O10ii | −60.6 (13) |
C25—C26—N4—C18 | 179.7 (6) | O11ii—Cl2—O11—O10ii | −47 (100) |
C21—C26—N4—C18 | 0.5 (9) | O10—Cl2—O11—O9ii | −56.9 (14) |
C25—C26—N4—Cu1 | 5.0 (9) | O10ii—Cl2—O11—O9ii | 123.1 (14) |
C21—C26—N4—Cu1 | −174.2 (5) | O9—Cl2—O11—O9ii | 180.000 (5) |
N1—Cu1—N4—C18 | 125.1 (5) | O8ii—Cl2—O11—O9ii | −117.5 (13) |
N3—Cu1—N4—C18 | −125.5 (4) | O8—Cl2—O11—O9ii | 62.5 (13) |
N5—Cu1—N4—C18 | 2.4 (4) | O11ii—Cl2—O11—O9ii | 76 (100) |
N1—Cu1—N4—C26 | −60.0 (7) | O10—Cl2—O11—O8ii | 60.6 (13) |
N3—Cu1—N4—C26 | 49.4 (6) | O10ii—Cl2—O11—O8ii | −119.4 (13) |
N5—Cu1—N4—C26 | 177.3 (6) | O9—Cl2—O11—O8ii | −62.5 (13) |
O3—C17—N5—N6 | −0.4 (8) | O9ii—Cl2—O11—O8ii | 117.5 (13) |
C18—C17—N5—N6 | −177.9 (6) | O8—Cl2—O11—O8ii | 180.000 (5) |
O3—C17—N5—Cu1 | 173.2 (4) | O11ii—Cl2—O11—O8ii | −167 (100) |
C18—C17—N5—Cu1 | −4.3 (8) | N2—C11—S1—C12 | 3.7 (8) |
N4—Cu1—N5—C17 | 0.9 (5) | O2—C11—S1—C12 | −177.2 (6) |
N1—Cu1—N5—C17 | −136.3 (5) | C13—C12—S1—C11 | 177.7 (6) |
N3—Cu1—N5—C17 | 123.2 (5) | N6—C16—S2—C15 | −4.3 (8) |
N4—Cu1—N5—N6 | 169.9 (8) | O3—C16—S2—C15 | 174.4 (5) |
N1—Cu1—N5—N6 | 32.7 (8) | C14i—C15—S2—C16 | −75.4 (6) |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z; (iv) −x, −y, −z+1. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register