A family of rare structurally different homometal multinuclear CuII bis(salamo)-based complexes, [Cu4(L)2(MeOH)2](ClO4)2·2MeOH (1), [Cu4(L)2(EtOH)2](NO3)2·2EtOH (2) and [Cu2(HL)(EtOH)Br2]·CHCl3 (3), has been successfully synthesized by the reactions of cupric salts with a bis(salamo)-based multidentate chelate ligand (H3L). The salamo-based ligand [R-CH=N—O—(CH2)n—O—N=CH—R] is a new type of salen-based analog. Complexes (1) and (2) are isostructural structures, and crystallize in monoclinic space group P21/n with centrosymmetric spiral structures, where the main structures contain two fully deprotonated ligand (L)3− units, a charged tetranuclear CuII folding center and two coordinated solvent molecules. Complex (3) crystallizes in monoclinic space group Cc and consists of two CuII cations, one incompletely deprotonated ligand (HL)2− unit and one coordinated ethanol molecule, and forms a novel homo-binuclear CuII complex structure due to Br− counter anions. Complexes (1)–(3) have zero-dimensional cluster-based structures and are further assembled into three-dimensional frameworks via intermolecular interactions. Because of the different solvents and counter anions which have a significant influence on the structures of complexes (1)–(3), the interactions were quantitatively evaluated by Hirshfeld surfaces analyses. Complexes (1)–(3) have been characterized by elemental analyses, IR spectra, UV–vis spectra and X-ray crystallography analyses. In addition, fluorescence properties are evaluated and DFT calculations are performed.
Supporting information
CCDC references: 2052695; 2052696; 2052697
Cell refinement: SAINT V8.38A (?, 2016) for (3). Data reduction: SAINT V8.38A (?, 2016) for (3). For all structures, program(s) used to solve structure: olex2.solve (Bourhis et al., 2015). Program(s) used to refine structure: olex2.refine (Bourhis et al., 2015) for (1), (2); SHELXL (Sheldrick, 2015) for (3). For all structures, molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
Crystal data top
C56H54Cu4N12O24·2(ClO4)·2(CH4O) | F(000) = 1832 |
Mr = 1796.25 | Dx = 1.744 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 15.2568 (4) Å | Cell parameters from 9913 reflections |
b = 14.5155 (4) Å | θ = 2.4–26.7° |
c = 15.4550 (4) Å | µ = 1.41 mm−1 |
β = 92.086 (1)° | T = 173 K |
V = 3420.40 (16) Å3 | BLOCK |
Z = 2 | 0.24 × 0.22 × 0.19 mm |
Data collection top
Bruker D8 Venture diffractometer | 6759 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
phi and ω scans | θmax = 26.7°, θmin = 2.3° |
Absorption correction: multi-scan SADABS | h = −19→19 |
Tmin = 0.659, Tmax = 0.745 | k = −18→18 |
43196 measured reflections | l = −19→17 |
7259 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.034P)2 + 5.5923P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
7259 reflections | Δρmax = 1.76 e Å−3 |
530 parameters | Δρmin = −0.84 e Å−3 |
24 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.91994 (2) | 0.42705 (2) | 0.47503 (2) | 0.02062 (8) | |
Cu2 | 0.81008 (2) | 0.54391 (2) | 0.32847 (2) | 0.02363 (8) | |
O1 | 0.99904 (11) | 0.50320 (11) | 0.40949 (10) | 0.0237 (3) | |
O2 | 1.1402 (2) | 0.4285 (2) | 0.04653 (15) | 0.0771 (9) | |
O3 | 1.16494 (17) | 0.2965 (2) | 0.10245 (15) | 0.0596 (7) | |
O4 | 1.01646 (12) | 0.26020 (12) | 0.53252 (11) | 0.0319 (4) | |
O5 | 0.84267 (13) | 0.27639 (12) | 0.58260 (11) | 0.0326 (4) | |
O6 | 0.82819 (11) | 0.51845 (11) | 0.45155 (10) | 0.0234 (3) | |
O7 | 0.82668 (13) | 0.75794 (13) | 0.31108 (12) | 0.0368 (4) | |
O8 | 0.76207 (13) | 0.64490 (14) | 0.17251 (12) | 0.0362 (4) | |
O9 | 0.84128 (12) | 0.41440 (12) | 0.31032 (11) | 0.0289 (4) | |
O10 | 0.98332 (17) | 0.2922 (2) | −0.04492 (18) | 0.0700 (8) | |
O11 | 1.0022 (2) | 0.1669 (2) | 0.0280 (2) | 0.0813 (10) | |
O12 | 0.66230 (13) | 0.52197 (16) | 0.33764 (13) | 0.0429 (5) | |
H12 | 0.6317 (12) | 0.519 (2) | 0.2890 (9) | 0.064* | |
N1 | 1.14247 (17) | 0.3761 (2) | 0.10805 (15) | 0.0464 (7) | |
N2 | 1.00387 (13) | 0.32580 (14) | 0.46466 (12) | 0.0241 (4) | |
N3 | 0.83437 (13) | 0.36773 (13) | 0.55317 (13) | 0.0239 (4) | |
N4 | 0.80778 (14) | 0.68020 (14) | 0.36246 (13) | 0.0266 (4) | |
N5 | 0.80502 (15) | 0.56364 (16) | 0.20435 (13) | 0.0308 (5) | |
N6 | 0.97630 (18) | 0.2464 (2) | 0.0207 (2) | 0.0582 (8) | |
C1 | 1.03816 (15) | 0.47239 (17) | 0.34105 (14) | 0.0225 (4) | |
C2 | 1.06584 (15) | 0.37967 (17) | 0.33332 (15) | 0.0238 (5) | |
C3 | 1.10456 (16) | 0.34945 (19) | 0.25788 (16) | 0.0295 (5) | |
H3 | 1.1249 | 0.2879 | 0.2531 | 0.035* | |
C4 | 1.11278 (16) | 0.4105 (2) | 0.19058 (15) | 0.0325 (6) | |
C5 | 1.09085 (17) | 0.5031 (2) | 0.19807 (16) | 0.0339 (6) | |
H5 | 1.0998 | 0.5444 | 0.1515 | 0.041* | |
C6 | 1.05612 (16) | 0.53422 (19) | 0.27343 (16) | 0.0290 (5) | |
H6 | 1.0441 | 0.5980 | 0.2801 | 0.035* | |
C7 | 1.05748 (15) | 0.31437 (17) | 0.40359 (15) | 0.0255 (5) | |
H7 | 1.0933 | 0.2608 | 0.4044 | 0.031* | |
C8 | 0.95615 (19) | 0.18486 (18) | 0.52274 (19) | 0.0357 (6) | |
H8A | 0.9628 | 0.1441 | 0.5739 | 0.043* | |
H8B | 0.9712 | 0.1485 | 0.4711 | 0.043* | |
C9 | 0.86210 (18) | 0.21537 (18) | 0.51311 (18) | 0.0329 (6) | |
H9A | 0.8522 | 0.2473 | 0.4570 | 0.039* | |
H9B | 0.8229 | 0.1611 | 0.5141 | 0.039* | |
C10 | 0.77784 (16) | 0.41121 (17) | 0.59732 (15) | 0.0267 (5) | |
H10 | 0.7488 | 0.3780 | 0.6408 | 0.032* | |
C11 | 0.75547 (15) | 0.50714 (17) | 0.58532 (15) | 0.0251 (5) | |
C12 | 0.78022 (15) | 0.55751 (16) | 0.51221 (15) | 0.0226 (4) | |
C13 | 0.75395 (15) | 0.65006 (17) | 0.50536 (15) | 0.0257 (5) | |
C14 | 0.70756 (17) | 0.69077 (18) | 0.57170 (16) | 0.0308 (5) | |
H14 | 0.6931 | 0.7543 | 0.5675 | 0.037* | |
C15 | 0.68193 (18) | 0.6416 (2) | 0.64357 (17) | 0.0337 (6) | |
C16 | 0.70581 (17) | 0.54948 (19) | 0.64842 (16) | 0.0312 (5) | |
H16 | 0.6878 | 0.5139 | 0.6962 | 0.037* | |
C17 | 0.6318 (2) | 0.6874 (2) | 0.7139 (2) | 0.0503 (8) | |
H17A | 0.6730 | 0.7101 | 0.7591 | 0.076* | |
H17B | 0.5917 | 0.6428 | 0.7390 | 0.076* | |
H17C | 0.5979 | 0.7392 | 0.6894 | 0.076* | |
C18 | 0.77861 (16) | 0.70874 (17) | 0.43431 (16) | 0.0275 (5) | |
H18 | 0.7726 | 0.7734 | 0.4417 | 0.033* | |
C19 | 0.88018 (18) | 0.7363 (2) | 0.24016 (19) | 0.0384 (6) | |
H19A | 0.9165 | 0.6815 | 0.2547 | 0.046* | |
H19B | 0.9201 | 0.7884 | 0.2294 | 0.046* | |
C20 | 0.8249 (2) | 0.7173 (2) | 0.15990 (19) | 0.0418 (7) | |
H20A | 0.7934 | 0.7742 | 0.1422 | 0.050* | |
H20B | 0.8635 | 0.6996 | 0.1125 | 0.050* | |
C21 | 0.83001 (18) | 0.5104 (2) | 0.14403 (16) | 0.0352 (6) | |
H21 | 0.8238 | 0.5319 | 0.0861 | 0.042* | |
C22 | 0.86678 (17) | 0.4204 (2) | 0.15805 (17) | 0.0328 (6) | |
C23 | 0.86576 (16) | 0.37506 (18) | 0.23964 (16) | 0.0288 (5) | |
C24 | 0.89341 (18) | 0.28137 (19) | 0.24222 (19) | 0.0356 (6) | |
H24 | 0.8877 | 0.2470 | 0.2941 | 0.043* | |
C25 | 0.92804 (19) | 0.2396 (2) | 0.1715 (2) | 0.0429 (7) | |
H25 | 0.9475 | 0.1775 | 0.1750 | 0.051* | |
C26 | 0.93441 (18) | 0.2888 (2) | 0.0946 (2) | 0.0432 (7) | |
C27 | 0.90222 (18) | 0.3760 (2) | 0.08640 (18) | 0.0403 (7) | |
H27 | 0.9037 | 0.4068 | 0.0322 | 0.048* | |
C28 | 0.6151 (2) | 0.4694 (2) | 0.3978 (2) | 0.0492 (8) | |
H28A | 0.5620 | 0.4443 | 0.3690 | 0.074* | |
H28B | 0.5987 | 0.5089 | 0.4460 | 0.074* | |
H28C | 0.6519 | 0.4187 | 0.4199 | 0.074* | |
Cl1 | 0.33320 (6) | 0.56949 (6) | 0.12328 (6) | 0.0574 (2) | |
O13 | 0.5620 (4) | 0.4776 (6) | 0.1930 (4) | 0.0611 (19) | 0.547 (15) |
H13 | 0.5155 | 0.5084 | 0.1882 | 0.092* | 0.547 (15) |
O13A | 0.5677 (6) | 0.5340 (13) | 0.1909 (6) | 0.095 (4) | 0.453 (15) |
H13A | 0.5193 | 0.5563 | 0.1739 | 0.143* | 0.453 (15) |
O14 | 0.4164 (6) | 0.6041 (7) | 0.1665 (8) | 0.091 (3) | 0.547 (15) |
O14A | 0.4202 (6) | 0.5912 (10) | 0.1198 (11) | 0.101 (4) | 0.453 (15) |
O15 | 0.3299 (8) | 0.6125 (6) | 0.0459 (4) | 0.074 (3) | 0.547 (15) |
O15A | 0.2779 (9) | 0.5877 (6) | 0.0419 (5) | 0.081 (3) | 0.453 (15) |
O16 | 0.3268 (2) | 0.47310 (17) | 0.13361 (18) | 0.0745 (9) | |
O17 | 0.2807 (3) | 0.6142 (2) | 0.1861 (2) | 0.0921 (11) | |
C29 | 0.6033 (3) | 0.4814 (3) | 0.1205 (3) | 0.0741 (12) | |
H29A | 0.5622 | 0.4680 | 0.0719 | 0.111* | 0.547 (15) |
H29B | 0.6507 | 0.4359 | 0.1217 | 0.111* | 0.547 (15) |
H29C | 0.6280 | 0.5432 | 0.1134 | 0.111* | 0.547 (15) |
H29D | 0.5610 | 0.4808 | 0.0713 | 0.111* | 0.453 (15) |
H29E | 0.6149 | 0.4181 | 0.1398 | 0.111* | 0.453 (15) |
H29F | 0.6581 | 0.5099 | 0.1029 | 0.111* | 0.453 (15) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.02309 (14) | 0.02021 (14) | 0.01900 (14) | 0.00196 (10) | 0.00665 (10) | 0.00251 (10) |
Cu2 | 0.02706 (15) | 0.02623 (15) | 0.01779 (14) | 0.00225 (11) | 0.00347 (11) | 0.00262 (11) |
O1 | 0.0279 (8) | 0.0235 (8) | 0.0201 (7) | −0.0011 (6) | 0.0084 (6) | 0.0002 (6) |
O2 | 0.102 (2) | 0.107 (2) | 0.0236 (11) | 0.0061 (18) | 0.0272 (13) | 0.0058 (13) |
O3 | 0.0575 (15) | 0.0799 (19) | 0.0425 (13) | 0.0120 (13) | 0.0197 (11) | −0.0205 (12) |
O4 | 0.0345 (9) | 0.0309 (9) | 0.0304 (9) | 0.0043 (7) | 0.0020 (7) | 0.0136 (7) |
O5 | 0.0458 (11) | 0.0240 (9) | 0.0291 (9) | 0.0049 (8) | 0.0159 (8) | 0.0082 (7) |
O6 | 0.0264 (8) | 0.0260 (8) | 0.0181 (7) | 0.0047 (7) | 0.0059 (6) | 0.0024 (6) |
O7 | 0.0501 (12) | 0.0258 (9) | 0.0348 (10) | −0.0026 (8) | 0.0049 (8) | 0.0107 (8) |
O8 | 0.0383 (10) | 0.0411 (11) | 0.0291 (9) | 0.0041 (8) | −0.0004 (8) | 0.0109 (8) |
O9 | 0.0344 (9) | 0.0287 (9) | 0.0240 (8) | 0.0003 (7) | 0.0044 (7) | −0.0019 (7) |
O10 | 0.0537 (15) | 0.108 (2) | 0.0501 (15) | −0.0144 (15) | 0.0230 (12) | −0.0359 (16) |
O11 | 0.0686 (18) | 0.079 (2) | 0.098 (2) | 0.0049 (15) | 0.0267 (16) | −0.0525 (18) |
O12 | 0.0349 (11) | 0.0584 (13) | 0.0353 (11) | 0.0004 (9) | 0.0018 (8) | 0.0060 (10) |
N1 | 0.0354 (13) | 0.079 (2) | 0.0259 (12) | −0.0005 (13) | 0.0115 (10) | −0.0095 (13) |
N2 | 0.0274 (10) | 0.0231 (10) | 0.0221 (9) | 0.0013 (8) | 0.0037 (8) | 0.0044 (8) |
N3 | 0.0277 (10) | 0.0195 (9) | 0.0247 (10) | 0.0010 (8) | 0.0054 (8) | 0.0050 (8) |
N4 | 0.0294 (10) | 0.0246 (10) | 0.0258 (10) | −0.0009 (8) | −0.0002 (8) | 0.0078 (8) |
N5 | 0.0328 (11) | 0.0367 (12) | 0.0231 (10) | 0.0028 (9) | 0.0039 (8) | 0.0060 (9) |
N6 | 0.0394 (15) | 0.078 (2) | 0.0582 (19) | −0.0093 (15) | 0.0135 (13) | −0.0406 (17) |
C1 | 0.0200 (10) | 0.0304 (12) | 0.0172 (10) | −0.0014 (9) | 0.0016 (8) | −0.0006 (9) |
C2 | 0.0208 (11) | 0.0296 (12) | 0.0212 (11) | −0.0010 (9) | 0.0032 (9) | −0.0027 (9) |
C3 | 0.0227 (11) | 0.0378 (14) | 0.0284 (12) | 0.0002 (10) | 0.0049 (9) | −0.0074 (10) |
C4 | 0.0244 (12) | 0.0555 (17) | 0.0182 (11) | −0.0026 (11) | 0.0075 (9) | −0.0051 (11) |
C5 | 0.0289 (13) | 0.0531 (17) | 0.0201 (11) | −0.0028 (12) | 0.0053 (10) | 0.0089 (11) |
C6 | 0.0260 (12) | 0.0355 (13) | 0.0259 (12) | 0.0005 (10) | 0.0038 (9) | 0.0065 (10) |
C7 | 0.0238 (11) | 0.0252 (11) | 0.0276 (12) | 0.0019 (9) | 0.0026 (9) | −0.0028 (9) |
C8 | 0.0429 (15) | 0.0238 (12) | 0.0414 (15) | 0.0041 (11) | 0.0132 (12) | 0.0062 (11) |
C9 | 0.0385 (14) | 0.0241 (12) | 0.0368 (14) | −0.0045 (10) | 0.0117 (11) | −0.0004 (10) |
C10 | 0.0281 (12) | 0.0300 (12) | 0.0225 (11) | −0.0010 (10) | 0.0078 (9) | 0.0037 (9) |
C11 | 0.0239 (11) | 0.0290 (12) | 0.0227 (11) | 0.0034 (9) | 0.0041 (9) | 0.0005 (9) |
C12 | 0.0205 (11) | 0.0271 (12) | 0.0202 (11) | 0.0021 (9) | 0.0016 (8) | −0.0020 (9) |
C13 | 0.0254 (11) | 0.0285 (12) | 0.0231 (11) | 0.0030 (9) | −0.0010 (9) | −0.0010 (9) |
C14 | 0.0330 (13) | 0.0301 (13) | 0.0294 (12) | 0.0089 (10) | 0.0001 (10) | −0.0046 (10) |
C15 | 0.0336 (13) | 0.0422 (15) | 0.0254 (12) | 0.0118 (11) | 0.0043 (10) | −0.0053 (11) |
C16 | 0.0322 (13) | 0.0400 (14) | 0.0218 (11) | 0.0064 (11) | 0.0070 (10) | 0.0015 (10) |
C17 | 0.064 (2) | 0.0543 (19) | 0.0338 (15) | 0.0271 (16) | 0.0167 (14) | −0.0030 (14) |
C18 | 0.0283 (12) | 0.0235 (11) | 0.0306 (12) | 0.0032 (9) | −0.0032 (10) | 0.0004 (10) |
C19 | 0.0300 (13) | 0.0437 (16) | 0.0419 (15) | −0.0029 (12) | 0.0068 (11) | 0.0173 (13) |
C20 | 0.0458 (16) | 0.0469 (17) | 0.0335 (14) | 0.0026 (13) | 0.0092 (12) | 0.0173 (13) |
C21 | 0.0345 (14) | 0.0509 (16) | 0.0205 (12) | −0.0029 (12) | 0.0058 (10) | 0.0022 (11) |
C22 | 0.0287 (13) | 0.0438 (15) | 0.0262 (12) | −0.0050 (11) | 0.0057 (10) | −0.0069 (11) |
C23 | 0.0229 (11) | 0.0354 (13) | 0.0283 (12) | −0.0039 (10) | 0.0030 (9) | −0.0064 (10) |
C24 | 0.0317 (13) | 0.0338 (14) | 0.0413 (15) | −0.0045 (11) | 0.0021 (11) | −0.0099 (12) |
C25 | 0.0321 (14) | 0.0410 (16) | 0.0557 (18) | −0.0038 (12) | 0.0027 (13) | −0.0212 (14) |
C26 | 0.0293 (13) | 0.0570 (19) | 0.0439 (16) | −0.0078 (13) | 0.0088 (12) | −0.0281 (15) |
C27 | 0.0335 (14) | 0.0584 (19) | 0.0296 (13) | −0.0092 (13) | 0.0080 (11) | −0.0135 (13) |
C28 | 0.0446 (17) | 0.0513 (19) | 0.0523 (19) | −0.0155 (14) | 0.0078 (14) | −0.0079 (15) |
Cl1 | 0.0605 (5) | 0.0420 (4) | 0.0715 (6) | 0.0092 (4) | 0.0254 (4) | 0.0297 (4) |
O13 | 0.056 (3) | 0.067 (4) | 0.059 (3) | −0.011 (3) | −0.015 (2) | 0.017 (3) |
O13A | 0.065 (5) | 0.160 (10) | 0.060 (4) | 0.001 (6) | −0.013 (3) | 0.016 (6) |
O14 | 0.100 (5) | 0.069 (4) | 0.107 (7) | −0.003 (4) | 0.030 (5) | 0.025 (5) |
O14A | 0.060 (4) | 0.107 (7) | 0.138 (9) | −0.003 (4) | 0.050 (6) | 0.066 (7) |
O15 | 0.106 (7) | 0.062 (4) | 0.055 (3) | 0.003 (4) | 0.010 (4) | 0.023 (3) |
O15A | 0.111 (8) | 0.053 (4) | 0.077 (5) | −0.014 (4) | −0.032 (5) | 0.028 (3) |
O16 | 0.126 (3) | 0.0364 (13) | 0.0611 (17) | 0.0134 (15) | 0.0021 (17) | 0.0067 (12) |
O17 | 0.123 (3) | 0.073 (2) | 0.083 (2) | 0.034 (2) | 0.045 (2) | 0.0097 (17) |
C29 | 0.068 (3) | 0.063 (3) | 0.090 (3) | −0.010 (2) | −0.017 (2) | −0.004 (2) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.9477 (16) | C10—C11 | 1.444 (3) |
Cu1—O1i | 2.3618 (17) | C11—C12 | 1.409 (3) |
Cu1—O6 | 1.9530 (16) | C11—C16 | 1.399 (3) |
Cu1—N2 | 1.960 (2) | C12—C13 | 1.405 (3) |
Cu1—N3 | 2.0048 (19) | C13—C14 | 1.398 (3) |
Cu2—O6 | 1.9476 (16) | C13—C18 | 1.450 (3) |
Cu2—O9 | 1.9618 (18) | C14—H14 | 0.9500 |
Cu2—O12 | 2.286 (2) | C14—C15 | 1.388 (4) |
Cu2—N4 | 2.048 (2) | C15—C16 | 1.388 (4) |
Cu2—N5 | 1.938 (2) | C15—C17 | 1.507 (4) |
O1—Cu1i | 2.3618 (17) | C16—H16 | 0.9500 |
O1—C1 | 1.312 (3) | C17—H17A | 0.9800 |
O2—N1 | 1.217 (4) | C17—H17B | 0.9800 |
O3—N1 | 1.209 (4) | C17—H17C | 0.9800 |
O4—N2 | 1.424 (2) | C18—H18 | 0.9500 |
O4—C8 | 1.434 (3) | C19—H19A | 0.9900 |
O5—N3 | 1.406 (2) | C19—H19B | 0.9900 |
O5—C9 | 1.431 (3) | C19—C20 | 1.500 (4) |
O6—C12 | 1.336 (3) | C20—H20A | 0.9900 |
O7—N4 | 1.415 (3) | C20—H20B | 0.9900 |
O7—C19 | 1.425 (3) | C21—H21 | 0.9500 |
O8—N5 | 1.428 (3) | C21—C22 | 1.435 (4) |
O8—C20 | 1.440 (4) | C22—C23 | 1.423 (4) |
O9—C23 | 1.299 (3) | C22—C27 | 1.407 (4) |
O10—N6 | 1.220 (4) | C23—C24 | 1.424 (4) |
O11—N6 | 1.223 (5) | C24—H24 | 0.9500 |
O12—H12 | 0.872 (9) | C24—C25 | 1.372 (4) |
O12—C28 | 1.419 (4) | C25—H25 | 0.9500 |
N1—C4 | 1.457 (3) | C25—C26 | 1.393 (5) |
N2—C7 | 1.282 (3) | C26—C27 | 1.362 (5) |
N3—C10 | 1.285 (3) | C27—H27 | 0.9500 |
N4—C18 | 1.280 (3) | C28—H28A | 0.9800 |
N5—C21 | 1.279 (3) | C28—H28B | 0.9800 |
N6—C26 | 1.465 (4) | C28—H28C | 0.9800 |
C1—C2 | 1.417 (3) | Cl1—O14 | 1.500 (9) |
C1—C6 | 1.412 (3) | Cl1—O14A | 1.368 (9) |
C2—C3 | 1.397 (3) | Cl1—O15 | 1.348 (5) |
C2—C7 | 1.451 (3) | Cl1—O15A | 1.512 (8) |
C3—H3 | 0.9500 | Cl1—O16 | 1.412 (3) |
C3—C4 | 1.375 (4) | Cl1—O17 | 1.436 (3) |
C4—C5 | 1.391 (4) | O13—H13 | 0.8401 |
C5—H5 | 0.9500 | O13—C29 | 1.307 (8) |
C5—C6 | 1.373 (4) | O13A—H13A | 0.8400 |
C6—H6 | 0.9500 | O13A—C29 | 1.451 (11) |
C7—H7 | 0.9500 | C29—H29A | 0.9800 |
C8—H8A | 0.9900 | C29—H29B | 0.9800 |
C8—H8B | 0.9900 | C29—H29C | 0.9800 |
C8—C9 | 1.504 (4) | C29—H29D | 0.9800 |
C9—H9A | 0.9900 | C29—H29E | 0.9800 |
C9—H9B | 0.9900 | C29—H29F | 0.9800 |
C10—H10 | 0.9500 | | |
| | | |
O1—Cu1—O1i | 80.36 (6) | C16—C11—C12 | 119.9 (2) |
O1—Cu1—O6 | 88.36 (7) | O6—C12—C11 | 120.8 (2) |
O1—Cu1—N2 | 87.94 (7) | O6—C12—C13 | 121.0 (2) |
O1—Cu1—N3 | 170.57 (7) | C13—C12—C11 | 118.2 (2) |
O6—Cu1—O1i | 101.60 (6) | C12—C13—C18 | 122.5 (2) |
O6—Cu1—N2 | 163.80 (8) | C14—C13—C12 | 120.0 (2) |
O6—Cu1—N3 | 85.73 (7) | C14—C13—C18 | 117.3 (2) |
N2—Cu1—O1i | 93.31 (7) | C13—C14—H14 | 118.8 |
N2—Cu1—N3 | 99.73 (8) | C15—C14—C13 | 122.3 (2) |
N3—Cu1—O1i | 93.63 (7) | C15—C14—H14 | 118.8 |
O6—Cu2—O9 | 86.06 (7) | C14—C15—C17 | 121.1 (3) |
O6—Cu2—O12 | 91.04 (7) | C16—C15—C14 | 117.2 (2) |
O6—Cu2—N4 | 86.32 (7) | C16—C15—C17 | 121.7 (3) |
O9—Cu2—O12 | 96.91 (8) | C11—C16—H16 | 118.9 |
O9—Cu2—N4 | 165.70 (8) | C15—C16—C11 | 122.2 (2) |
N4—Cu2—O12 | 95.31 (8) | C15—C16—H16 | 118.9 |
N5—Cu2—O6 | 173.61 (8) | C15—C17—H17A | 109.5 |
N5—Cu2—O9 | 90.07 (8) | C15—C17—H17B | 109.5 |
N5—Cu2—O12 | 94.48 (8) | C15—C17—H17C | 109.5 |
N5—Cu2—N4 | 96.36 (9) | H17A—C17—H17B | 109.5 |
Cu1—O1—Cu1i | 99.64 (6) | H17A—C17—H17C | 109.5 |
C1—O1—Cu1 | 122.31 (15) | H17B—C17—H17C | 109.5 |
C1—O1—Cu1i | 120.97 (14) | N4—C18—C13 | 125.1 (2) |
N2—O4—C8 | 111.31 (19) | N4—C18—H18 | 117.5 |
N3—O5—C9 | 111.07 (17) | C13—C18—H18 | 117.5 |
Cu2—O6—Cu1 | 112.68 (8) | O7—C19—H19A | 109.5 |
C12—O6—Cu1 | 124.40 (14) | O7—C19—H19B | 109.5 |
C12—O6—Cu2 | 122.88 (14) | O7—C19—C20 | 110.8 (2) |
N4—O7—C19 | 112.9 (2) | H19A—C19—H19B | 108.1 |
N5—O8—C20 | 110.5 (2) | C20—C19—H19A | 109.5 |
C23—O9—Cu2 | 128.31 (17) | C20—C19—H19B | 109.5 |
Cu2—O12—H12 | 116.9 (13) | O8—C20—C19 | 112.3 (2) |
C28—O12—Cu2 | 129.85 (19) | O8—C20—H20A | 109.1 |
C28—O12—H12 | 105.4 (14) | O8—C20—H20B | 109.1 |
O2—N1—C4 | 118.0 (3) | C19—C20—H20A | 109.1 |
O3—N1—O2 | 122.8 (3) | C19—C20—H20B | 109.1 |
O3—N1—C4 | 119.2 (3) | H20A—C20—H20B | 107.9 |
O4—N2—Cu1 | 120.80 (14) | N5—C21—H21 | 117.8 |
C7—N2—Cu1 | 126.41 (17) | N5—C21—C22 | 124.4 (2) |
C7—N2—O4 | 112.52 (19) | C22—C21—H21 | 117.8 |
O5—N3—Cu1 | 123.16 (14) | C23—C22—C21 | 122.6 (2) |
C10—N3—Cu1 | 124.99 (17) | C27—C22—C21 | 117.3 (3) |
C10—N3—O5 | 110.23 (18) | C27—C22—C23 | 120.2 (3) |
O7—N4—Cu2 | 128.35 (15) | O9—C23—C22 | 123.7 (2) |
C18—N4—Cu2 | 123.03 (17) | O9—C23—C24 | 119.3 (2) |
C18—N4—O7 | 108.2 (2) | C22—C23—C24 | 117.0 (2) |
O8—N5—Cu2 | 117.66 (15) | C23—C24—H24 | 119.3 |
C21—N5—Cu2 | 129.0 (2) | C25—C24—C23 | 121.5 (3) |
C21—N5—O8 | 113.1 (2) | C25—C24—H24 | 119.3 |
O10—N6—O11 | 123.5 (3) | C24—C25—H25 | 120.2 |
O10—N6—C26 | 118.3 (3) | C24—C25—C26 | 119.5 (3) |
O11—N6—C26 | 118.2 (4) | C26—C25—H25 | 120.2 |
O1—C1—C2 | 122.5 (2) | C25—C26—N6 | 119.7 (3) |
O1—C1—C6 | 119.1 (2) | C27—C26—N6 | 118.9 (3) |
C6—C1—C2 | 118.3 (2) | C27—C26—C25 | 121.4 (3) |
C1—C2—C7 | 121.5 (2) | C22—C27—H27 | 120.0 |
C3—C2—C1 | 120.3 (2) | C26—C27—C22 | 120.0 (3) |
C3—C2—C7 | 118.1 (2) | C26—C27—H27 | 120.0 |
C2—C3—H3 | 120.6 | O12—C28—H28A | 109.5 |
C4—C3—C2 | 118.8 (2) | O12—C28—H28B | 109.5 |
C4—C3—H3 | 120.6 | O12—C28—H28C | 109.5 |
C3—C4—N1 | 118.8 (3) | H28A—C28—H28B | 109.5 |
C3—C4—C5 | 122.0 (2) | H28A—C28—H28C | 109.5 |
C5—C4—N1 | 119.1 (2) | H28B—C28—H28C | 109.5 |
C4—C5—H5 | 120.3 | O14A—Cl1—O15A | 116.1 (6) |
C6—C5—C4 | 119.3 (2) | O14A—Cl1—O16 | 107.7 (6) |
C6—C5—H5 | 120.3 | O14A—Cl1—O17 | 119.2 (8) |
C1—C6—H6 | 119.7 | O15—Cl1—O14 | 104.0 (5) |
C5—C6—C1 | 120.7 (2) | O15—Cl1—O16 | 124.0 (4) |
C5—C6—H6 | 119.7 | O15—Cl1—O17 | 112.8 (3) |
N2—C7—C2 | 122.9 (2) | O16—Cl1—O14 | 110.0 (4) |
N2—C7—H7 | 118.6 | O16—Cl1—O15A | 103.2 (4) |
C2—C7—H7 | 118.6 | O16—Cl1—O17 | 109.19 (19) |
O4—C8—H8A | 109.0 | O17—Cl1—O14 | 91.8 (5) |
O4—C8—H8B | 109.0 | O17—Cl1—O15A | 100.1 (5) |
O4—C8—C9 | 113.1 (2) | C29—O13—H13 | 109.5 |
H8A—C8—H8B | 107.8 | C29—O13A—H13A | 108.4 |
C9—C8—H8A | 109.0 | O13—C29—H29A | 109.5 |
C9—C8—H8B | 109.0 | O13—C29—H29B | 109.5 |
O5—C9—C8 | 109.3 (2) | O13—C29—H29C | 109.5 |
O5—C9—H9A | 109.8 | O13A—C29—H29D | 109.5 |
O5—C9—H9B | 109.8 | O13A—C29—H29E | 109.5 |
C8—C9—H9A | 109.8 | O13A—C29—H29F | 109.5 |
C8—C9—H9B | 109.8 | H29A—C29—H29B | 109.5 |
H9A—C9—H9B | 108.3 | H29A—C29—H29C | 109.5 |
N3—C10—H10 | 117.8 | H29B—C29—H29C | 109.5 |
N3—C10—C11 | 124.4 (2) | H29D—C29—H29E | 109.5 |
C11—C10—H10 | 117.8 | H29D—C29—H29F | 109.5 |
C12—C11—C10 | 122.3 (2) | H29E—C29—H29F | 109.5 |
C16—C11—C10 | 117.7 (2) | | |
| | | |
Cu1i—O1—C1—C2 | 93.6 (2) | C1—C2—C7—N2 | 20.9 (4) |
Cu1—O1—C1—C2 | −34.1 (3) | C2—C1—C6—C5 | 7.0 (4) |
Cu1i—O1—C1—C6 | −84.4 (2) | C2—C3—C4—N1 | −172.1 (2) |
Cu1—O1—C1—C6 | 148.02 (18) | C2—C3—C4—C5 | 5.7 (4) |
Cu1—O6—C12—C11 | −35.1 (3) | C3—C2—C7—N2 | −160.9 (2) |
Cu1—O6—C12—C13 | 144.14 (18) | C3—C4—C5—C6 | −3.0 (4) |
Cu1—N2—C7—C2 | 2.8 (3) | C4—C5—C6—C1 | −3.5 (4) |
Cu1—N3—C10—C11 | 12.4 (4) | C6—C1—C2—C3 | −4.2 (3) |
Cu2—O6—C12—C11 | 142.36 (18) | C6—C1—C2—C7 | 173.9 (2) |
Cu2—O6—C12—C13 | −38.4 (3) | C7—C2—C3—C4 | 179.8 (2) |
Cu2—O9—C23—C22 | −5.8 (4) | C8—O4—N2—Cu1 | 88.3 (2) |
Cu2—O9—C23—C24 | 174.20 (17) | C8—O4—N2—C7 | −97.3 (2) |
Cu2—N4—C18—C13 | 8.2 (3) | C9—O5—N3—Cu1 | −46.3 (2) |
Cu2—N5—C21—C22 | 1.4 (4) | C9—O5—N3—C10 | 147.6 (2) |
O1—C1—C2—C3 | 177.8 (2) | C10—C11—C12—O6 | −1.9 (4) |
O1—C1—C2—C7 | −4.0 (3) | C10—C11—C12—C13 | 178.8 (2) |
O1—C1—C6—C5 | −175.0 (2) | C10—C11—C16—C15 | 179.1 (2) |
O2—N1—C4—C3 | 172.0 (3) | C11—C12—C13—C14 | 2.5 (3) |
O2—N1—C4—C5 | −5.8 (4) | C11—C12—C13—C18 | 177.8 (2) |
O3—N1—C4—C3 | −5.1 (4) | C12—C11—C16—C15 | −2.3 (4) |
O3—N1—C4—C5 | 177.0 (3) | C12—C13—C14—C15 | −3.4 (4) |
O4—N2—C7—C2 | −171.3 (2) | C12—C13—C18—N4 | 16.9 (4) |
O4—C8—C9—O5 | −52.3 (3) | C13—C14—C15—C16 | 1.3 (4) |
O5—N3—C10—C11 | 178.2 (2) | C13—C14—C15—C17 | −179.8 (3) |
O6—C12—C13—C14 | −176.8 (2) | C14—C13—C18—N4 | −167.7 (2) |
O6—C12—C13—C18 | −1.5 (4) | C14—C15—C16—C11 | 1.5 (4) |
O7—N4—C18—C13 | −178.3 (2) | C16—C11—C12—O6 | 179.5 (2) |
O7—C19—C20—O8 | −56.2 (3) | C16—C11—C12—C13 | 0.2 (3) |
O8—N5—C21—C22 | −173.5 (2) | C17—C15—C16—C11 | −177.3 (3) |
O9—C23—C24—C25 | −173.4 (2) | C18—C13—C14—C15 | −178.9 (2) |
O10—N6—C26—C25 | −177.8 (3) | C19—O7—N4—Cu2 | −22.4 (3) |
O10—N6—C26—C27 | 2.3 (4) | C19—O7—N4—C18 | 164.6 (2) |
O11—N6—C26—C25 | 2.3 (4) | C20—O8—N5—Cu2 | 95.3 (2) |
O11—N6—C26—C27 | −177.5 (3) | C20—O8—N5—C21 | −89.1 (3) |
N1—C4—C5—C6 | 174.8 (2) | C21—C22—C23—O9 | −8.3 (4) |
N2—O4—C8—C9 | −53.1 (3) | C21—C22—C23—C24 | 171.7 (2) |
N3—O5—C9—C8 | 107.5 (2) | C21—C22—C27—C26 | −177.0 (3) |
N3—C10—C11—C12 | 13.4 (4) | C22—C23—C24—C25 | 6.6 (4) |
N3—C10—C11—C16 | −168.0 (2) | C23—C22—C27—C26 | 1.0 (4) |
N4—O7—C19—C20 | 93.9 (3) | C23—C24—C25—C26 | −1.7 (4) |
N5—O8—C20—C19 | −54.5 (3) | C24—C25—C26—N6 | 176.2 (3) |
N5—C21—C22—C23 | 10.7 (4) | C24—C25—C26—C27 | −3.9 (4) |
N5—C21—C22—C27 | −171.3 (3) | C25—C26—C27—C22 | 4.2 (4) |
N6—C26—C27—C22 | −175.9 (2) | C27—C22—C23—O9 | 173.8 (2) |
C1—C2—C3—C4 | −2.0 (4) | C27—C22—C23—C24 | −6.2 (4) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Crystal data top
C58H58Cu4N12O24·2(NO3)·2(C2H6O) | F(000) = 1824 |
Mr = 1777.48 | Dx = 1.690 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 15.1553 (6) Å | Cell parameters from 3115 reflections |
b = 15.2135 (6) Å | θ = 2.1–25.2° |
c = 15.1959 (6) Å | µ = 1.31 mm−1 |
β = 94.292 (1)° | T = 173 K |
V = 3493.8 (2) Å3 | Block |
Z = 2 | 0.17 × 0.14 × 0.13 mm |
Data collection top
Bruker D8 Venture diffractometer | Rint = 0.044 |
Absorption correction: multi-scan | θmax = 26.8°, θmin = 2.3° |
Tmin = 0.81, Tmax = 0.85 | h = −19→19 |
35111 measured reflections | k = −19→19 |
7413 independent reflections | l = −19→19 |
5276 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
7413 reflections | Δρmax = 0.23 e Å−3 |
509 parameters | Δρmin = −0.24 e Å−3 |
2 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.33791 (18) | 0.5227 (2) | 1.03790 (19) | 0.0335 (7) | |
C2 | 0.32845 (19) | 0.6117 (2) | 1.06068 (19) | 0.0340 (7) | |
C3 | 0.25315 (19) | 0.6403 (2) | 1.10234 (18) | 0.0380 (7) | |
H3 | 0.245337 | 0.700376 | 1.116829 | 0.046* | |
C4 | 0.19249 (19) | 0.5787 (2) | 1.12082 (19) | 0.0371 (7) | |
C5 | 0.20186 (18) | 0.4897 (2) | 1.10392 (18) | 0.0342 (7) | |
H5 | 0.159270 | 0.448467 | 1.120978 | 0.041* | |
C6 | 0.2745 (2) | 0.4627 (2) | 1.0618 (2) | 0.0377 (7) | |
H6 | 0.281483 | 0.402159 | 1.048774 | 0.045* | |
C7 | 0.3959 (2) | 0.6771 (2) | 1.0472 (2) | 0.0400 (8) | |
H7 | 0.393123 | 0.731693 | 1.077210 | 0.048* | |
C8 | 0.5085 (2) | 0.8015 (2) | 0.9450 (2) | 0.0379 (7) | |
H8A | 0.558021 | 0.843999 | 0.951181 | 0.045* | |
H8B | 0.453831 | 0.832676 | 0.958862 | 0.045* | |
C9 | 0.49813 (19) | 0.76860 (19) | 0.8513 (2) | 0.0380 (7) | |
H9A | 0.442366 | 0.734871 | 0.841837 | 0.046* | |
H9B | 0.495073 | 0.819118 | 0.810094 | 0.046* | |
C10 | 0.58975 (19) | 0.5846 (2) | 0.7724 (2) | 0.0358 (7) | |
H10 | 0.630050 | 0.618199 | 0.741227 | 0.043* | |
C11 | 0.58350 (19) | 0.4919 (2) | 0.75353 (19) | 0.0360 (7) | |
C12 | 0.51482 (19) | 0.43971 (19) | 0.78010 (19) | 0.0328 (6) | |
C13 | 0.51294 (19) | 0.3513 (2) | 0.75695 (19) | 0.0379 (8) | |
C14 | 0.5808 (2) | 0.3159 (2) | 0.7100 (2) | 0.0396 (8) | |
H14 | 0.579497 | 0.255125 | 0.695550 | 0.048* | |
C15 | 0.65043 (19) | 0.3682 (2) | 0.68396 (19) | 0.0375 (7) | |
C16 | 0.64744 (19) | 0.4567 (2) | 0.7040 (2) | 0.0355 (7) | |
H16 | 0.690970 | 0.494591 | 0.682874 | 0.043* | |
C17 | 0.7222 (2) | 0.3281 (2) | 0.6334 (2) | 0.0455 (8) | |
H17A | 0.764695 | 0.373769 | 0.619599 | 0.068* | |
H17B | 0.695945 | 0.302279 | 0.578506 | 0.068* | |
H17C | 0.752772 | 0.282289 | 0.669329 | 0.068* | |
C18 | 0.44666 (19) | 0.2905 (2) | 0.78443 (19) | 0.0356 (7) | |
H18 | 0.457987 | 0.229494 | 0.778524 | 0.043* | |
C19 | 0.26186 (19) | 0.2536 (2) | 0.89600 (19) | 0.0379 (7) | |
H19A | 0.276646 | 0.307907 | 0.929811 | 0.045* | |
H19B | 0.258949 | 0.204507 | 0.938472 | 0.045* | |
C20 | 0.17413 (19) | 0.2642 (2) | 0.8456 (2) | 0.0415 (8) | |
H20A | 0.157010 | 0.207652 | 0.816884 | 0.050* | |
H20B | 0.129096 | 0.278748 | 0.887246 | 0.050* | |
C21 | 0.1416 (2) | 0.4602 (2) | 0.8401 (2) | 0.0380 (8) | |
H21 | 0.084054 | 0.435174 | 0.838443 | 0.046* | |
C22 | 0.15151 (19) | 0.5496 (2) | 0.86787 (19) | 0.0366 (7) | |
C23 | 0.2306 (2) | 0.5988 (2) | 0.85973 (19) | 0.0361 (7) | |
C24 | 0.22802 (19) | 0.6905 (2) | 0.8787 (2) | 0.0374 (7) | |
H24 | 0.277182 | 0.726519 | 0.867730 | 0.045* | |
C25 | 0.15494 (19) | 0.7272 (2) | 0.91294 (19) | 0.0381 (7) | |
H25 | 0.154435 | 0.788197 | 0.926490 | 0.046* | |
C26 | 0.0827 (2) | 0.6761 (2) | 0.9275 (2) | 0.0419 (8) | |
C27 | 0.0784 (2) | 0.5907 (2) | 0.9026 (2) | 0.0390 (8) | |
H27 | 0.025617 | 0.558220 | 0.908558 | 0.047* | |
C28 | 0.3976 (3) | 0.5074 (2) | 0.5471 (2) | 0.0626 (11) | |
H28A | 0.442454 | 0.461224 | 0.556456 | 0.094* | |
H28B | 0.425323 | 0.560899 | 0.526152 | 0.094* | |
H28C | 0.351376 | 0.487710 | 0.502934 | 0.094* | |
C29 | 0.3589 (2) | 0.5255 (2) | 0.6292 (2) | 0.0469 (9) | |
H29A | 0.308877 | 0.566953 | 0.618388 | 0.056* | |
H29B | 0.403559 | 0.553564 | 0.671006 | 0.056* | |
C30 | 0.0982 (2) | 0.5265 (2) | 0.6231 (2) | 0.0500 (9) | |
H30A | 0.064378 | 0.478950 | 0.648242 | 0.075* | |
H30B | 0.059851 | 0.577828 | 0.612250 | 0.075* | |
H30C | 0.148265 | 0.542343 | 0.664643 | 0.075* | |
C31 | 0.1323 (2) | 0.4961 (2) | 0.5370 (2) | 0.0482 (9) | |
H31A | 0.082069 | 0.483734 | 0.493280 | 0.058* | |
H31B | 0.169357 | 0.542525 | 0.512808 | 0.058* | |
Cu1 | 0.47140 (2) | 0.56651 (2) | 0.91649 (2) | 0.03352 (11) | |
Cu2 | 0.32899 (2) | 0.43912 (2) | 0.81502 (2) | 0.03459 (11) | |
N1 | 0.11334 (17) | 0.6093 (2) | 1.16244 (17) | 0.0427 (7) | |
N2 | 0.45940 (15) | 0.66496 (15) | 0.99640 (16) | 0.0343 (6) | |
N3 | 0.54430 (15) | 0.62579 (15) | 0.82910 (16) | 0.0341 (6) | |
N4 | 0.37470 (16) | 0.31276 (15) | 0.81575 (16) | 0.0352 (6) | |
N5 | 0.20406 (16) | 0.41196 (16) | 0.81750 (16) | 0.0382 (6) | |
N6 | 0.00632 (17) | 0.71417 (19) | 0.96823 (17) | 0.0423 (7) | |
N7 | 0.1785 (2) | 0.36510 (18) | 0.3330 (2) | 0.0481 (7) | |
O1 | 0.40638 (12) | 0.49447 (12) | 0.99615 (12) | 0.0341 (5) | |
O2 | 0.06763 (15) | 0.55226 (16) | 1.19597 (16) | 0.0539 (6) | |
O3 | 0.09506 (15) | 0.68610 (16) | 1.16139 (15) | 0.0521 (6) | |
O4 | 0.52541 (13) | 0.73042 (13) | 1.00717 (13) | 0.0389 (5) | |
O5 | 0.57089 (13) | 0.71405 (13) | 0.83391 (13) | 0.0387 (5) | |
O6 | 0.45305 (12) | 0.47279 (13) | 0.82991 (13) | 0.0360 (5) | |
O7 | 0.32853 (13) | 0.23625 (13) | 0.83797 (14) | 0.0403 (5) | |
O8 | 0.17448 (13) | 0.33125 (13) | 0.77977 (14) | 0.0399 (5) | |
O9 | 0.30322 (13) | 0.56362 (12) | 0.83457 (13) | 0.0350 (5) | |
O10 | −0.05610 (15) | 0.66677 (15) | 0.98053 (15) | 0.0505 (6) | |
O11 | 0.00997 (14) | 0.79181 (15) | 0.98864 (14) | 0.0492 (6) | |
O12 | 0.32757 (13) | 0.44537 (13) | 0.66761 (13) | 0.0392 (5) | |
H12B | 0.265983 | 0.435494 | 0.643134 | 0.047* | |
O13 | 0.18392 (14) | 0.41751 (14) | 0.55423 (14) | 0.0448 (6) | |
H13 | 0.199378 | 0.397015 | 0.506407 | 0.067* | |
O14 | 0.23843 (15) | 0.37232 (16) | 0.39305 (15) | 0.0544 (6) | |
O15 | 0.19887 (15) | 0.35885 (16) | 0.25515 (16) | 0.0574 (6) | |
O16 | 0.09853 (15) | 0.36182 (14) | 0.34977 (14) | 0.0484 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0226 (15) | 0.047 (2) | 0.0299 (17) | 0.0073 (14) | −0.0047 (14) | −0.0050 (14) |
C2 | 0.0302 (16) | 0.044 (2) | 0.0276 (16) | 0.0030 (14) | −0.0025 (13) | 0.0045 (14) |
C3 | 0.0373 (17) | 0.049 (2) | 0.0279 (17) | 0.0046 (15) | 0.0048 (14) | −0.0052 (14) |
C4 | 0.0294 (16) | 0.0549 (15) | 0.0280 (16) | 0.0111 (15) | 0.0081 (14) | −0.0057 (14) |
C5 | 0.0265 (15) | 0.0457 (14) | 0.0311 (16) | −0.0080 (13) | 0.0071 (14) | 0.0083 (13) |
C6 | 0.0375 (18) | 0.0415 (19) | 0.0346 (18) | −0.0036 (14) | 0.0053 (15) | −0.0081 (14) |
C7 | 0.0369 (18) | 0.043 (2) | 0.0395 (19) | 0.0030 (14) | 0.0017 (16) | 0.0010 (14) |
C8 | 0.0378 (17) | 0.0352 (18) | 0.0412 (18) | −0.0070 (14) | 0.0059 (15) | −0.0007 (14) |
C9 | 0.0376 (17) | 0.0370 (18) | 0.0394 (18) | 0.0044 (14) | 0.0033 (15) | 0.0099 (14) |
C10 | 0.0271 (15) | 0.043 (2) | 0.0372 (18) | 0.0059 (13) | 0.0029 (14) | 0.0097 (14) |
C11 | 0.0336 (16) | 0.045 (2) | 0.0295 (17) | 0.0058 (12) | 0.0054 (14) | −0.0052 (14) |
C12 | 0.0306 (15) | 0.0400 (18) | 0.0268 (15) | 0.0039 (12) | −0.0057 (13) | −0.0068 (13) |
C13 | 0.0294 (16) | 0.049 (2) | 0.0334 (17) | −0.0023 (14) | −0.0108 (14) | −0.0084 (15) |
C14 | 0.0363 (17) | 0.0437 (19) | 0.0367 (18) | 0.0131 (15) | −0.0120 (15) | −0.0093 (14) |
C15 | 0.0316 (16) | 0.051 (2) | 0.0306 (17) | 0.0103 (14) | 0.0095 (14) | −0.0095 (14) |
C16 | 0.0295 (16) | 0.043 (2) | 0.0358 (17) | −0.0027 (13) | 0.0117 (14) | 0.0035 (14) |
C17 | 0.0403 (18) | 0.052 (2) | 0.046 (2) | 0.0071 (15) | 0.0139 (16) | −0.0120 (16) |
C18 | 0.0309 (16) | 0.0388 (18) | 0.0354 (17) | 0.0062 (14) | −0.0084 (14) | −0.0106 (14) |
C19 | 0.0397 (18) | 0.0437 (19) | 0.0312 (17) | −0.0146 (14) | 0.0098 (15) | 0.0102 (14) |
C20 | 0.0349 (17) | 0.0394 (19) | 0.052 (2) | −0.0105 (14) | 0.0163 (16) | −0.0082 (16) |
C21 | 0.0309 (17) | 0.045 (2) | 0.0385 (18) | −0.0079 (14) | 0.0074 (15) | −0.0074 (14) |
C22 | 0.0348 (17) | 0.044 (2) | 0.0323 (17) | 0.0086 (14) | 0.0068 (14) | 0.0060 (14) |
C23 | 0.0341 (17) | 0.0450 (19) | 0.0290 (17) | 0.0025 (15) | 0.0018 (14) | 0.0084 (14) |
C24 | 0.0321 (17) | 0.0408 (19) | 0.0375 (18) | −0.0058 (14) | −0.0086 (15) | 0.0083 (14) |
C25 | 0.0386 (17) | 0.0407 (19) | 0.0331 (18) | 0.0121 (15) | −0.0096 (15) | 0.0085 (14) |
C26 | 0.0404 (19) | 0.047 (2) | 0.0393 (19) | 0.0120 (15) | 0.0087 (16) | 0.0082 (15) |
C27 | 0.0357 (17) | 0.045 (2) | 0.0374 (18) | −0.0094 (14) | 0.0099 (15) | 0.0073 (15) |
C28 | 0.073 (3) | 0.054 (2) | 0.064 (3) | −0.018 (2) | 0.028 (2) | 0.0161 (19) |
C29 | 0.053 (2) | 0.046 (2) | 0.039 (2) | −0.0086 (17) | −0.0106 (17) | 0.0102 (16) |
C30 | 0.049 (2) | 0.052 (2) | 0.048 (2) | 0.0097 (17) | −0.0065 (18) | −0.0083 (17) |
C31 | 0.046 (2) | 0.046 (2) | 0.050 (2) | 0.0148 (16) | −0.0121 (17) | 0.0067 (16) |
Cu1 | 0.0306 (2) | 0.0389 (2) | 0.0319 (2) | −0.00670 (16) | 0.00786 (17) | 0.00623 (16) |
Cu2 | 0.0294 (2) | 0.0392 (2) | 0.0357 (2) | −0.00614 (16) | 0.00610 (17) | −0.00706 (17) |
N1 | 0.0350 (15) | 0.056 (2) | 0.0389 (16) | 0.0030 (15) | 0.0138 (13) | −0.0124 (14) |
N2 | 0.0294 (13) | 0.0387 (15) | 0.0337 (14) | −0.0065 (11) | −0.0047 (12) | 0.0060 (11) |
N3 | 0.0333 (14) | 0.0336 (15) | 0.0357 (14) | −0.0082 (11) | 0.0055 (12) | 0.0080 (11) |
N4 | 0.0363 (14) | 0.0335 (15) | 0.0369 (15) | −0.0047 (11) | 0.0089 (12) | 0.0077 (11) |
N5 | 0.0377 (15) | 0.0382 (16) | 0.0396 (15) | −0.0064 (12) | 0.0085 (13) | −0.0101 (12) |
N6 | 0.0390 (16) | 0.0447 (18) | 0.0441 (17) | 0.0095 (14) | 0.0097 (13) | −0.0116 (13) |
N7 | 0.0527 (19) | 0.0490 (18) | 0.0412 (18) | −0.0131 (14) | −0.0059 (17) | 0.0157 (13) |
O1 | 0.0314 (11) | 0.0410 (13) | 0.0313 (11) | 0.0037 (9) | 0.0112 (9) | 0.0085 (9) |
O2 | 0.0411 (13) | 0.0646 (17) | 0.0581 (16) | −0.0069 (12) | 0.0175 (12) | −0.0152 (12) |
O3 | 0.0499 (14) | 0.0556 (16) | 0.0528 (15) | 0.0184 (12) | 0.0165 (12) | −0.0113 (12) |
O4 | 0.0368 (11) | 0.0434 (13) | 0.0353 (12) | −0.0079 (10) | −0.0057 (10) | 0.0047 (10) |
O5 | 0.0363 (11) | 0.0360 (13) | 0.0454 (13) | −0.0038 (10) | 0.0134 (10) | 0.0061 (10) |
O6 | 0.0293 (11) | 0.0421 (12) | 0.0372 (12) | −0.0073 (9) | 0.0062 (10) | −0.0017 (10) |
O7 | 0.0360 (12) | 0.0408 (13) | 0.0446 (13) | −0.0108 (10) | 0.0076 (10) | −0.0067 (10) |
O8 | 0.0343 (12) | 0.0401 (13) | 0.0456 (13) | −0.0076 (9) | 0.0055 (10) | −0.0092 (10) |
O9 | 0.0277 (10) | 0.0387 (12) | 0.0375 (12) | −0.0047 (9) | −0.0038 (9) | 0.0065 (9) |
O10 | 0.0416 (13) | 0.0560 (15) | 0.0557 (15) | −0.0037 (12) | 0.0152 (12) | −0.0170 (12) |
O11 | 0.0517 (14) | 0.0473 (15) | 0.0501 (14) | 0.0166 (11) | 0.0135 (12) | −0.0091 (12) |
O12 | 0.0371 (12) | 0.0471 (14) | 0.0319 (11) | −0.0077 (10) | −0.0077 (10) | 0.0071 (9) |
O13 | 0.0411 (13) | 0.0475 (14) | 0.0440 (13) | −0.0099 (10) | −0.0079 (11) | −0.0084 (11) |
O14 | 0.0463 (14) | 0.0674 (17) | 0.0476 (14) | −0.0090 (12) | −0.0095 (13) | 0.0089 (12) |
O15 | 0.0554 (15) | 0.0668 (17) | 0.0512 (16) | −0.0173 (12) | 0.0122 (13) | 0.0104 (13) |
O16 | 0.0432 (14) | 0.0529 (15) | 0.0508 (14) | −0.0095 (11) | 0.0143 (12) | 0.0097 (11) |
Geometric parameters (Å, º) top
C1—C2 | 1.406 (4) | C21—N5 | 1.265 (4) |
C1—C6 | 1.393 (4) | C22—C23 | 1.427 (4) |
C1—O1 | 1.328 (3) | C22—C27 | 1.409 (4) |
C2—C3 | 1.415 (4) | C23—C24 | 1.425 (4) |
C2—C7 | 1.453 (4) | C23—O9 | 1.307 (3) |
C3—H3 | 0.9500 | C24—H24 | 0.9500 |
C3—C4 | 1.357 (4) | C24—C25 | 1.377 (4) |
C4—C5 | 1.387 (4) | C25—H25 | 0.9500 |
C4—N1 | 1.473 (4) | C25—C26 | 1.374 (4) |
C5—H5 | 0.9500 | C26—C27 | 1.354 (4) |
C5—C6 | 1.377 (4) | C26—N6 | 1.472 (4) |
C6—H6 | 0.9500 | C27—H27 | 0.9500 |
C7—H7 | 0.9500 | C28—H28A | 0.9800 |
C7—N2 | 1.291 (4) | C28—H28B | 0.9800 |
C8—H8A | 0.9900 | C28—H28C | 0.9800 |
C8—H8B | 0.9900 | C28—C29 | 1.445 (5) |
C8—C9 | 1.507 (4) | C29—H29A | 0.9900 |
C8—O4 | 1.446 (3) | C29—H29B | 0.9900 |
C9—H9A | 0.9900 | C29—O12 | 1.447 (4) |
C9—H9B | 0.9900 | C30—H30A | 0.9800 |
C9—O5 | 1.421 (3) | C30—H30B | 0.9800 |
C10—H10 | 0.9500 | C30—H30C | 0.9800 |
C10—C11 | 1.440 (4) | C30—C31 | 1.515 (4) |
C10—N3 | 1.303 (4) | C31—H31A | 0.9900 |
C11—C12 | 1.393 (4) | C31—H31B | 0.9900 |
C11—C16 | 1.379 (4) | C31—O13 | 1.443 (4) |
C12—C13 | 1.390 (4) | Cu1—N2 | 1.945 (2) |
C12—O6 | 1.345 (3) | Cu1—N3 | 2.004 (2) |
C13—C14 | 1.402 (4) | Cu1—O1i | 2.3845 (19) |
C13—C18 | 1.450 (4) | Cu1—O1 | 1.9535 (18) |
C14—H14 | 0.9500 | Cu1—O6 | 1.946 (2) |
C14—C15 | 1.403 (4) | Cu2—N4 | 2.043 (2) |
C15—C16 | 1.381 (4) | Cu2—N5 | 1.941 (2) |
C15—C17 | 1.507 (4) | Cu2—O6 | 1.9455 (19) |
C16—H16 | 0.9500 | Cu2—O9 | 1.961 (2) |
C17—H17A | 0.9800 | Cu2—O12 | 2.240 (2) |
C17—H17B | 0.9800 | N1—O2 | 1.244 (3) |
C17—H17C | 0.9800 | N1—O3 | 1.200 (3) |
C18—H18 | 0.9500 | N2—O4 | 1.412 (3) |
C18—N4 | 1.268 (3) | N3—O5 | 1.402 (3) |
C19—H19A | 0.9900 | N4—O7 | 1.412 (3) |
C19—H19B | 0.9900 | N5—O8 | 1.414 (3) |
C19—C20 | 1.493 (4) | N6—O10 | 1.215 (3) |
C19—O7 | 1.415 (3) | N6—O11 | 1.222 (3) |
C20—H20A | 0.9900 | N7—O14 | 1.244 (3) |
C20—H20B | 0.9900 | N7—O15 | 1.249 (3) |
C20—O8 | 1.429 (4) | N7—O16 | 1.257 (3) |
C21—H21 | 0.9500 | O12—H12B | 0.9900 |
C21—C22 | 1.428 (4) | O13—H13 | 0.8400 |
| | | |
C6—C1—C2 | 118.8 (3) | C26—C25—C24 | 120.2 (3) |
O1—C1—C2 | 121.8 (3) | C26—C25—H25 | 119.9 |
O1—C1—C6 | 119.4 (3) | C25—C26—N6 | 120.4 (3) |
C1—C2—C3 | 120.4 (3) | C27—C26—C25 | 121.4 (3) |
C1—C2—C7 | 122.6 (3) | C27—C26—N6 | 118.1 (3) |
C3—C2—C7 | 116.9 (3) | C22—C27—H27 | 119.7 |
C2—C3—H3 | 121.2 | C26—C27—C22 | 120.5 (3) |
C4—C3—C2 | 117.5 (3) | C26—C27—H27 | 119.7 |
C4—C3—H3 | 121.2 | H28A—C28—H28B | 109.5 |
C3—C4—C5 | 123.7 (3) | H28A—C28—H28C | 109.5 |
C3—C4—N1 | 117.1 (3) | H28B—C28—H28C | 109.5 |
C5—C4—N1 | 119.1 (3) | C29—C28—H28A | 109.5 |
C4—C5—H5 | 120.9 | C29—C28—H28B | 109.5 |
C6—C5—C4 | 118.3 (3) | C29—C28—H28C | 109.5 |
C6—C5—H5 | 120.9 | C28—C29—H29A | 109.5 |
C1—C6—H6 | 119.4 | C28—C29—H29B | 109.5 |
C5—C6—C1 | 121.1 (3) | C28—C29—O12 | 110.8 (3) |
C5—C6—H6 | 119.4 | H29A—C29—H29B | 108.1 |
C2—C7—H7 | 118.3 | O12—C29—H29A | 109.5 |
N2—C7—C2 | 123.4 (3) | O12—C29—H29B | 109.5 |
N2—C7—H7 | 118.3 | H30A—C30—H30B | 109.5 |
H8A—C8—H8B | 107.9 | H30A—C30—H30C | 109.5 |
C9—C8—H8A | 109.3 | H30B—C30—H30C | 109.5 |
C9—C8—H8B | 109.3 | C31—C30—H30A | 109.5 |
O4—C8—H8A | 109.3 | C31—C30—H30B | 109.5 |
O4—C8—H8B | 109.3 | C31—C30—H30C | 109.5 |
O4—C8—C9 | 111.7 (2) | C30—C31—H31A | 110.1 |
C8—C9—H9A | 109.7 | C30—C31—H31B | 110.1 |
C8—C9—H9B | 109.7 | H31A—C31—H31B | 108.4 |
H9A—C9—H9B | 108.2 | O13—C31—C30 | 108.1 (3) |
O5—C9—C8 | 110.0 (2) | O13—C31—H31A | 110.1 |
O5—C9—H9A | 109.7 | O13—C31—H31B | 110.1 |
O5—C9—H9B | 109.7 | N2—Cu1—N3 | 98.58 (10) |
C11—C10—H10 | 117.5 | N2—Cu1—O1i | 93.27 (8) |
N3—C10—H10 | 117.5 | N2—Cu1—O1 | 88.29 (9) |
N3—C10—C11 | 124.9 (3) | N2—Cu1—O6 | 166.15 (9) |
C12—C11—C10 | 122.7 (3) | N3—Cu1—O1i | 95.75 (8) |
C16—C11—C10 | 116.8 (3) | O1—Cu1—N3 | 172.59 (9) |
C16—C11—C12 | 120.5 (3) | O1—Cu1—O1i | 81.00 (8) |
C13—C12—C11 | 118.7 (3) | O6—Cu1—N3 | 86.54 (9) |
O6—C12—C11 | 121.1 (3) | O6—Cu1—O1 | 87.40 (8) |
O6—C12—C13 | 120.2 (3) | O6—Cu1—O1i | 99.04 (8) |
C12—C13—C14 | 119.9 (3) | N4—Cu2—O12 | 91.33 (9) |
C12—C13—C18 | 123.1 (3) | N5—Cu2—N4 | 97.49 (10) |
C14—C13—C18 | 116.8 (3) | N5—Cu2—O6 | 171.65 (9) |
C13—C14—H14 | 119.3 | N5—Cu2—O9 | 89.83 (9) |
C13—C14—C15 | 121.4 (3) | N5—Cu2—O12 | 95.28 (9) |
C15—C14—H14 | 119.3 | O6—Cu2—N4 | 85.57 (9) |
C14—C15—C17 | 120.1 (3) | O6—Cu2—O9 | 85.97 (8) |
C16—C15—C14 | 116.9 (3) | O6—Cu2—O12 | 92.41 (8) |
C16—C15—C17 | 122.9 (3) | O9—Cu2—N4 | 168.30 (9) |
C11—C16—H16 | 118.8 | O9—Cu2—O12 | 97.09 (8) |
C15—C16—C11 | 122.4 (3) | O2—N1—C4 | 116.8 (3) |
C15—C16—H16 | 118.8 | O3—N1—C4 | 119.8 (3) |
C15—C17—H17A | 109.5 | O3—N1—O2 | 123.4 (3) |
C15—C17—H17B | 109.5 | C7—N2—Cu1 | 126.3 (2) |
C15—C17—H17C | 109.5 | C7—N2—O4 | 112.5 (2) |
H17A—C17—H17B | 109.5 | O4—N2—Cu1 | 121.11 (17) |
H17A—C17—H17C | 109.5 | C10—N3—Cu1 | 124.5 (2) |
H17B—C17—H17C | 109.5 | C10—N3—O5 | 109.3 (2) |
C13—C18—H18 | 117.6 | O5—N3—Cu1 | 124.53 (17) |
N4—C18—C13 | 124.9 (3) | C18—N4—Cu2 | 123.3 (2) |
N4—C18—H18 | 117.6 | C18—N4—O7 | 109.0 (2) |
H19A—C19—H19B | 108.1 | O7—N4—Cu2 | 127.09 (17) |
C20—C19—H19A | 109.5 | C21—N5—Cu2 | 129.2 (2) |
C20—C19—H19B | 109.5 | C21—N5—O8 | 113.1 (2) |
O7—C19—H19A | 109.5 | O8—N5—Cu2 | 117.21 (17) |
O7—C19—H19B | 109.5 | O10—N6—C26 | 118.5 (3) |
O7—C19—C20 | 110.5 (2) | O10—N6—O11 | 123.8 (3) |
C19—C20—H20A | 109.0 | O11—N6—C26 | 117.7 (3) |
C19—C20—H20B | 109.0 | O14—N7—O15 | 118.8 (3) |
H20A—C20—H20B | 107.8 | O14—N7—O16 | 121.1 (3) |
O8—C20—C19 | 112.7 (2) | O15—N7—O16 | 120.0 (3) |
O8—C20—H20A | 109.0 | C1—O1—Cu1i | 117.54 (16) |
O8—C20—H20B | 109.0 | C1—O1—Cu1 | 124.26 (18) |
C22—C21—H21 | 117.7 | Cu1—O1—Cu1i | 99.00 (8) |
N5—C21—H21 | 117.7 | N2—O4—C8 | 111.2 (2) |
N5—C21—C22 | 124.6 (3) | N3—O5—C9 | 110.2 (2) |
C23—C22—C21 | 123.0 (3) | C12—O6—Cu1 | 125.76 (17) |
C27—C22—C21 | 117.7 (3) | C12—O6—Cu2 | 122.92 (17) |
C27—C22—C23 | 119.2 (3) | Cu1—O6—Cu2 | 111.07 (9) |
C24—C23—C22 | 117.5 (3) | N4—O7—C19 | 112.7 (2) |
O9—C23—C22 | 122.8 (3) | N5—O8—C20 | 110.7 (2) |
O9—C23—C24 | 119.8 (3) | C23—O9—Cu2 | 128.45 (19) |
C23—C24—H24 | 119.7 | C29—O12—Cu2 | 117.40 (17) |
C25—C24—C23 | 120.6 (3) | C29—O12—H12B | 107.7 |
C25—C24—H24 | 119.7 | Cu2—O12—H12B | 107.9 |
C24—C25—H25 | 119.9 | C31—O13—H13 | 109.5 |
Symmetry code: (i) −x+1, −y+1, −z+2. |
Crystal data top
C29H30Br2Cu2N6O12·CHCl3 | F(000) = 2112 |
Mr = 1060.86 | Dx = 1.796 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.3330 (4) Å | Cell parameters from 9688 reflections |
b = 17.1049 (4) Å | θ = 2.4–26.7° |
c = 16.3502 (5) Å | µ = 3.39 mm−1 |
β = 101.859 (2)° | T = 173 K |
V = 3922.93 (19) Å3 | Block |
Z = 4 | 0.26 × 0.24 × 0.23 mm |
Data collection top
Bruker D8 Venture diffractometer | 7711 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.048 |
Absorption correction: multi-scan SADABS | θmax = 26.8°, θmin = 2.4° |
Tmin = 0.607, Tmax = 0.745 | h = −18→18 |
35876 measured reflections | k = −21→21 |
8303 independent reflections | l = −20→20 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.0373P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.068 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.55 e Å−3 |
8303 reflections | Δρmin = −0.56 e Å−3 |
540 parameters | Absolute structure: Refined as an inversion twin. |
119 restraints | Absolute structure parameter: 0.023 (8) |
Primary atom site location: iterative | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Br1 | 0.51014 (3) | 0.58335 (3) | 0.61276 (3) | 0.03264 (11) | |
Br2 | 0.19557 (4) | 0.61898 (3) | 0.46705 (3) | 0.03903 (13) | |
C1 | 0.2776 (3) | 0.5489 (2) | 0.6849 (3) | 0.0211 (8) | |
C2 | 0.2944 (3) | 0.6299 (3) | 0.6963 (3) | 0.0265 (9) | |
H2 | 0.324182 | 0.657931 | 0.658518 | 0.032* | |
C3 | 0.2678 (3) | 0.6688 (3) | 0.7620 (3) | 0.0295 (9) | |
H3 | 0.279561 | 0.723227 | 0.769475 | 0.035* | |
C4 | 0.2238 (3) | 0.6279 (3) | 0.8172 (3) | 0.0285 (9) | |
C5 | 0.2077 (3) | 0.5493 (3) | 0.8094 (3) | 0.0263 (9) | |
H5 | 0.178553 | 0.522418 | 0.848477 | 0.032* | |
C6 | 0.2344 (3) | 0.5082 (3) | 0.7432 (3) | 0.0241 (8) | |
C7 | 0.2082 (3) | 0.4266 (3) | 0.7363 (3) | 0.0259 (9) | |
H7 | 0.173834 | 0.406737 | 0.775713 | 0.031* | |
C8 | 0.1670 (4) | 0.2608 (3) | 0.6147 (3) | 0.0351 (10) | |
H8A | 0.166724 | 0.295939 | 0.566477 | 0.042* | |
H8B | 0.103544 | 0.235786 | 0.607299 | 0.042* | |
C9 | 0.2414 (5) | 0.2001 (3) | 0.6178 (4) | 0.0437 (13) | |
H9A | 0.234210 | 0.160437 | 0.660145 | 0.052* | |
H9B | 0.232049 | 0.173629 | 0.562885 | 0.052* | |
C10 | 0.3989 (4) | 0.2706 (3) | 0.5298 (3) | 0.0294 (10) | |
H10 | 0.416165 | 0.216975 | 0.530681 | 0.035* | |
C11 | 0.4321 (3) | 0.3206 (2) | 0.4706 (3) | 0.0257 (9) | |
C12 | 0.4114 (3) | 0.4013 (2) | 0.4620 (3) | 0.0209 (8) | |
C13 | 0.4465 (3) | 0.4427 (3) | 0.3995 (3) | 0.0225 (8) | |
C14 | 0.4989 (3) | 0.4030 (3) | 0.3492 (3) | 0.0293 (10) | |
H14 | 0.520864 | 0.431438 | 0.306902 | 0.035* | |
C15 | 0.5204 (4) | 0.3233 (3) | 0.3581 (3) | 0.0329 (10) | |
C16 | 0.4870 (3) | 0.2839 (3) | 0.4193 (3) | 0.0317 (10) | |
H16 | 0.501282 | 0.229838 | 0.427321 | 0.038* | |
C17 | 0.5778 (5) | 0.2837 (4) | 0.3036 (4) | 0.0501 (15) | |
H17A | 0.542290 | 0.284222 | 0.245630 | 0.075* | |
H17B | 0.590292 | 0.229500 | 0.322152 | 0.075* | |
H17C | 0.638402 | 0.311330 | 0.307408 | 0.075* | |
C18 | 0.4301 (3) | 0.5248 (3) | 0.3803 (3) | 0.0246 (9) | |
H18 | 0.447120 | 0.542908 | 0.330447 | 0.030* | |
C19 | 0.4090 (5) | 0.7128 (3) | 0.4357 (3) | 0.0423 (13) | |
H19A | 0.478362 | 0.711790 | 0.459489 | 0.051* | |
H19B | 0.374469 | 0.710039 | 0.482139 | 0.051* | |
C20 | 0.3831 (4) | 0.7857 (3) | 0.3864 (3) | 0.0400 (12) | |
H20A | 0.318135 | 0.780975 | 0.351561 | 0.048* | |
H20B | 0.384117 | 0.830837 | 0.424473 | 0.048* | |
C21 | 0.4823 (4) | 0.8735 (3) | 0.2372 (3) | 0.0354 (11) | |
H21 | 0.517868 | 0.829135 | 0.226500 | 0.042* | |
C22 | 0.4829 (4) | 0.9450 (3) | 0.1864 (3) | 0.0350 (11) | |
C23 | 0.5251 (4) | 0.9412 (3) | 0.1161 (4) | 0.0369 (11) | |
C24 | 0.5307 (4) | 1.0068 (3) | 0.0679 (4) | 0.0447 (13) | |
H24 | 0.561494 | 1.003804 | 0.021801 | 0.054* | |
C25 | 0.4915 (4) | 1.0767 (3) | 0.0866 (4) | 0.0452 (13) | |
H25 | 0.494775 | 1.122039 | 0.053667 | 0.054* | |
C26 | 0.4479 (4) | 1.0792 (3) | 0.1536 (4) | 0.0476 (14) | |
C27 | 0.4433 (4) | 1.0149 (3) | 0.2061 (4) | 0.0432 (12) | |
H27 | 0.414291 | 1.019102 | 0.253136 | 0.052* | |
C28 | 0.6058 (7) | 0.3466 (8) | 0.6739 (7) | 0.106 (4) | |
H28A | 0.573877 | 0.323387 | 0.620719 | 0.159* | |
H28B | 0.655963 | 0.311182 | 0.702274 | 0.159* | |
H28C | 0.634246 | 0.396730 | 0.663385 | 0.159* | |
C29 | 0.5371 (5) | 0.3590 (4) | 0.7262 (5) | 0.0617 (17) | |
H29A | 0.571934 | 0.375740 | 0.782163 | 0.074* | |
H29B | 0.506292 | 0.308335 | 0.733174 | 0.074* | |
Cu1 | 0.31508 (4) | 0.39953 (3) | 0.60575 (3) | 0.02174 (11) | |
Cu2 | 0.34921 (3) | 0.55862 (3) | 0.52622 (3) | 0.02157 (12) | |
N1 | 0.1933 (3) | 0.6696 (3) | 0.8857 (3) | 0.0370 (10) | |
N2 | 0.2271 (3) | 0.3789 (2) | 0.6818 (2) | 0.0254 (8) | |
N3 | 0.3480 (3) | 0.2930 (2) | 0.5814 (2) | 0.0290 (8) | |
N4 | 0.3954 (3) | 0.5754 (2) | 0.4226 (2) | 0.0237 (7) | |
N5 | 0.4353 (3) | 0.8702 (2) | 0.2947 (3) | 0.0360 (9) | |
N6 | 0.4047 (5) | 1.1524 (3) | 0.1733 (4) | 0.0648 (16) | |
O1 | 0.2997 (2) | 0.51216 (17) | 0.62030 (18) | 0.0234 (6) | |
O2 | 0.2051 (3) | 0.7402 (2) | 0.8909 (3) | 0.0527 (11) | |
O3 | 0.1578 (3) | 0.6307 (2) | 0.9351 (2) | 0.0466 (9) | |
O4 | 0.1857 (3) | 0.30552 (19) | 0.6911 (2) | 0.0371 (8) | |
O5 | 0.3381 (3) | 0.23237 (19) | 0.6384 (2) | 0.0387 (8) | |
O6 | 0.3608 (2) | 0.43761 (16) | 0.50914 (18) | 0.0217 (6) | |
O7 | 0.3831 (2) | 0.64799 (17) | 0.38000 (19) | 0.0294 (7) | |
O8 | 0.4513 (3) | 0.7971 (2) | 0.3342 (2) | 0.0400 (8) | |
O9 | 0.5600 (3) | 0.8715 (2) | 0.0983 (3) | 0.0432 (9) | |
H9 | 0.601264 | 0.878456 | 0.069221 | 0.065* | |
O10 | 0.3725 (5) | 1.1552 (3) | 0.2370 (5) | 0.0880 (19) | |
O11 | 0.4049 (5) | 1.2086 (3) | 0.1261 (4) | 0.0887 (19) | |
O12 | 0.4629 (3) | 0.4161 (2) | 0.6960 (2) | 0.0373 (8) | |
H12 | 0.4972 (19) | 0.4563 (19) | 0.681 (3) | 0.056* | |
C30 | 0.7369 (11) | 0.4317 (14) | 0.8697 (15) | 0.100 (7) | 0.492 (7) |
H30 | 0.725321 | 0.384382 | 0.833161 | 0.120* | 0.492 (7) |
C30A | 0.7911 (14) | 0.5079 (9) | 0.8951 (12) | 0.087 (5) | 0.508 (7) |
H30A | 0.852597 | 0.536130 | 0.897341 | 0.104* | 0.508 (7) |
Cl0A | 0.8598 (5) | 0.4390 (7) | 0.9319 (6) | 0.140 (3) | 0.492 (7) |
Cl1 | 0.7239 (12) | 0.5184 (11) | 0.8160 (12) | 0.207 (5) | 0.492 (7) |
Cl1A | 0.7173 (3) | 0.5183 (3) | 0.7967 (3) | 0.0605 (11) | 0.508 (7) |
Cl2 | 0.6614 (4) | 0.4379 (4) | 0.9445 (4) | 0.115 (2) | 0.492 (7) |
Cl2A | 0.7357 (5) | 0.5416 (6) | 0.9723 (5) | 0.149 (3) | 0.508 (7) |
Cl3 | 0.8109 (9) | 0.4065 (4) | 0.9040 (6) | 0.139 (3) | 0.508 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0400 (2) | 0.0315 (2) | 0.0275 (2) | −0.0132 (2) | 0.00937 (18) | 0.00038 (18) |
Br2 | 0.0448 (3) | 0.0460 (3) | 0.0307 (2) | 0.0171 (2) | 0.0180 (2) | 0.0093 (2) |
C1 | 0.0231 (19) | 0.025 (2) | 0.0170 (19) | 0.0012 (16) | 0.0078 (15) | −0.0019 (16) |
C2 | 0.035 (2) | 0.023 (2) | 0.024 (2) | 0.0019 (17) | 0.0113 (17) | 0.0014 (16) |
C3 | 0.036 (2) | 0.022 (2) | 0.030 (2) | 0.0010 (18) | 0.0085 (18) | −0.0070 (17) |
C4 | 0.029 (2) | 0.036 (2) | 0.021 (2) | 0.0055 (19) | 0.0078 (17) | −0.0076 (18) |
C5 | 0.029 (2) | 0.036 (2) | 0.018 (2) | 0.0010 (18) | 0.0121 (16) | 0.0009 (17) |
C6 | 0.029 (2) | 0.026 (2) | 0.0196 (19) | 0.0000 (17) | 0.0088 (16) | 0.0004 (16) |
C7 | 0.032 (2) | 0.031 (2) | 0.018 (2) | −0.0031 (18) | 0.0125 (17) | 0.0061 (16) |
C8 | 0.051 (3) | 0.028 (2) | 0.031 (2) | −0.018 (2) | 0.020 (2) | −0.0027 (18) |
C9 | 0.075 (4) | 0.021 (2) | 0.044 (3) | −0.013 (2) | 0.033 (3) | 0.000 (2) |
C10 | 0.047 (3) | 0.019 (2) | 0.025 (2) | 0.0086 (19) | 0.0136 (19) | 0.0021 (16) |
C11 | 0.037 (2) | 0.0214 (19) | 0.020 (2) | 0.0062 (17) | 0.0098 (17) | 0.0007 (16) |
C12 | 0.024 (2) | 0.022 (2) | 0.0174 (19) | 0.0006 (16) | 0.0057 (16) | −0.0027 (15) |
C13 | 0.0250 (19) | 0.028 (2) | 0.0162 (19) | 0.0001 (16) | 0.0086 (15) | −0.0026 (15) |
C14 | 0.035 (2) | 0.035 (2) | 0.021 (2) | 0.0061 (19) | 0.0149 (19) | 0.0024 (18) |
C15 | 0.042 (3) | 0.035 (2) | 0.026 (2) | 0.016 (2) | 0.0160 (19) | 0.0017 (19) |
C16 | 0.041 (3) | 0.029 (2) | 0.027 (2) | 0.016 (2) | 0.0119 (19) | 0.0014 (18) |
C17 | 0.067 (4) | 0.054 (3) | 0.038 (3) | 0.031 (3) | 0.031 (3) | 0.009 (3) |
C18 | 0.031 (2) | 0.028 (2) | 0.018 (2) | −0.0017 (17) | 0.0110 (17) | 0.0015 (16) |
C19 | 0.080 (4) | 0.022 (2) | 0.028 (2) | −0.011 (2) | 0.020 (2) | −0.0001 (19) |
C20 | 0.065 (4) | 0.022 (2) | 0.041 (3) | −0.002 (2) | 0.029 (3) | 0.0022 (19) |
C21 | 0.036 (3) | 0.029 (2) | 0.044 (3) | −0.001 (2) | 0.014 (2) | 0.000 (2) |
C22 | 0.035 (2) | 0.029 (2) | 0.043 (3) | −0.006 (2) | 0.013 (2) | 0.004 (2) |
C23 | 0.033 (2) | 0.036 (2) | 0.042 (3) | −0.002 (2) | 0.009 (2) | 0.003 (2) |
C24 | 0.045 (3) | 0.047 (3) | 0.044 (3) | −0.007 (2) | 0.017 (2) | 0.012 (2) |
C25 | 0.051 (3) | 0.032 (3) | 0.052 (3) | −0.003 (2) | 0.007 (3) | 0.015 (2) |
C26 | 0.050 (3) | 0.030 (3) | 0.063 (4) | 0.000 (2) | 0.013 (3) | 0.008 (2) |
C27 | 0.047 (3) | 0.036 (3) | 0.050 (3) | −0.001 (2) | 0.019 (3) | 0.006 (2) |
C28 | 0.073 (6) | 0.145 (10) | 0.100 (7) | 0.019 (6) | 0.018 (5) | −0.027 (7) |
C29 | 0.067 (4) | 0.047 (3) | 0.068 (5) | 0.007 (3) | 0.008 (3) | 0.003 (3) |
Cu1 | 0.0332 (3) | 0.0155 (2) | 0.0206 (2) | −0.0021 (2) | 0.0150 (2) | 0.00117 (19) |
Cu2 | 0.0332 (3) | 0.0172 (2) | 0.0180 (2) | −0.0013 (2) | 0.01399 (19) | 0.00117 (19) |
N1 | 0.039 (2) | 0.044 (3) | 0.029 (2) | 0.0091 (19) | 0.0110 (17) | −0.0119 (18) |
N2 | 0.038 (2) | 0.0190 (17) | 0.0236 (18) | −0.0072 (15) | 0.0156 (15) | 0.0024 (14) |
N3 | 0.044 (2) | 0.0194 (17) | 0.0266 (19) | 0.0019 (16) | 0.0149 (16) | 0.0079 (14) |
N4 | 0.0357 (19) | 0.0175 (16) | 0.0209 (18) | −0.0006 (14) | 0.0129 (15) | 0.0042 (13) |
N5 | 0.046 (2) | 0.0224 (18) | 0.041 (2) | −0.0027 (17) | 0.0115 (19) | 0.0050 (16) |
N6 | 0.080 (4) | 0.030 (2) | 0.089 (5) | 0.008 (3) | 0.030 (4) | 0.008 (3) |
O1 | 0.0337 (16) | 0.0200 (14) | 0.0202 (14) | −0.0023 (12) | 0.0144 (12) | −0.0003 (11) |
O2 | 0.070 (3) | 0.040 (2) | 0.053 (2) | 0.008 (2) | 0.026 (2) | −0.0211 (19) |
O3 | 0.056 (2) | 0.059 (2) | 0.0305 (19) | 0.0118 (19) | 0.0217 (17) | −0.0060 (17) |
O4 | 0.064 (2) | 0.0249 (16) | 0.0310 (18) | −0.0197 (16) | 0.0291 (16) | −0.0034 (13) |
O5 | 0.058 (2) | 0.0237 (16) | 0.0396 (19) | 0.0035 (15) | 0.0225 (17) | 0.0181 (14) |
O6 | 0.0315 (15) | 0.0167 (13) | 0.0206 (15) | −0.0011 (12) | 0.0140 (12) | 0.0001 (11) |
O7 | 0.053 (2) | 0.0182 (14) | 0.0205 (15) | −0.0011 (13) | 0.0167 (14) | 0.0050 (11) |
O8 | 0.051 (2) | 0.0258 (17) | 0.048 (2) | 0.0005 (15) | 0.0194 (17) | 0.0135 (15) |
O9 | 0.051 (2) | 0.0347 (19) | 0.052 (2) | −0.0019 (16) | 0.0289 (19) | 0.0009 (16) |
O10 | 0.120 (5) | 0.043 (3) | 0.115 (5) | 0.025 (3) | 0.056 (4) | 0.004 (3) |
O11 | 0.124 (5) | 0.035 (2) | 0.109 (5) | 0.016 (3) | 0.027 (4) | 0.025 (3) |
O12 | 0.044 (2) | 0.0334 (18) | 0.0342 (19) | −0.0009 (15) | 0.0078 (16) | −0.0008 (15) |
C30 | 0.074 (11) | 0.118 (17) | 0.104 (16) | 0.044 (12) | 0.006 (11) | 0.043 (14) |
C30A | 0.090 (12) | 0.069 (10) | 0.092 (13) | −0.006 (9) | −0.002 (10) | −0.008 (9) |
Cl0A | 0.078 (3) | 0.174 (7) | 0.148 (6) | 0.002 (4) | −0.024 (4) | 0.021 (6) |
Cl1 | 0.183 (9) | 0.228 (10) | 0.204 (10) | 0.036 (8) | 0.026 (8) | 0.041 (9) |
Cl1A | 0.0417 (17) | 0.081 (3) | 0.060 (2) | −0.0033 (17) | 0.0151 (15) | 0.0030 (17) |
Cl2 | 0.099 (4) | 0.135 (5) | 0.121 (5) | 0.052 (3) | 0.042 (3) | 0.057 (4) |
Cl2A | 0.101 (4) | 0.226 (8) | 0.115 (5) | 0.019 (5) | 0.011 (4) | −0.035 (5) |
Cl3 | 0.193 (8) | 0.089 (4) | 0.127 (6) | 0.003 (5) | 0.017 (6) | 0.024 (4) |
Geometric parameters (Å, º) top
Br1—Cu2 | 2.4819 (7) | C20—O8 | 1.437 (6) |
Br2—Cu2 | 2.4445 (7) | C21—H21 | 0.9500 |
C1—C2 | 1.412 (6) | C21—C22 | 1.480 (7) |
C1—C6 | 1.422 (6) | C21—N5 | 1.264 (7) |
C1—O1 | 1.322 (5) | C22—C23 | 1.405 (8) |
C2—H2 | 0.9500 | C22—C27 | 1.390 (8) |
C2—C3 | 1.382 (6) | C23—C24 | 1.384 (7) |
C3—H3 | 0.9500 | C23—O9 | 1.348 (6) |
C3—C4 | 1.390 (7) | C24—H24 | 0.9500 |
C4—C5 | 1.367 (7) | C24—C25 | 1.381 (8) |
C4—N1 | 1.469 (5) | C25—H25 | 0.9500 |
C5—H5 | 0.9500 | C25—C26 | 1.370 (9) |
C5—C6 | 1.408 (6) | C26—C27 | 1.404 (8) |
C6—C7 | 1.443 (6) | C26—N6 | 1.461 (8) |
C7—H7 | 0.9500 | C27—H27 | 0.9500 |
C7—N2 | 1.279 (6) | C28—H28A | 0.9800 |
C8—H8A | 0.9900 | C28—H28B | 0.9800 |
C8—H8B | 0.9900 | C28—H28C | 0.9800 |
C8—C9 | 1.482 (8) | C28—C29 | 1.446 (12) |
C8—O4 | 1.442 (6) | C29—H29A | 0.9900 |
C9—H9A | 0.9900 | C29—H29B | 0.9900 |
C9—H9B | 0.9900 | C29—O12 | 1.454 (8) |
C9—O5 | 1.465 (7) | Cu1—N2 | 1.976 (4) |
C10—H10 | 0.9500 | Cu1—N3 | 1.943 (4) |
C10—C11 | 1.443 (6) | Cu1—O1 | 1.959 (3) |
C10—N3 | 1.282 (6) | Cu1—O6 | 1.943 (3) |
C11—C12 | 1.413 (6) | Cu1—O12 | 2.337 (4) |
C11—C16 | 1.410 (6) | Cu2—N4 | 1.962 (4) |
C12—C13 | 1.418 (6) | Cu2—O1 | 1.987 (3) |
C12—O6 | 1.317 (5) | Cu2—O6 | 2.100 (3) |
C13—C14 | 1.400 (6) | N1—O2 | 1.220 (6) |
C13—C18 | 1.447 (6) | N1—O3 | 1.233 (6) |
C14—H14 | 0.9500 | N2—O4 | 1.410 (4) |
C14—C15 | 1.398 (7) | N3—O5 | 1.421 (4) |
C15—C16 | 1.371 (7) | N4—O7 | 1.417 (4) |
C15—C17 | 1.494 (6) | N5—O8 | 1.404 (5) |
C16—H16 | 0.9500 | N6—O10 | 1.225 (8) |
C17—H17A | 0.9800 | N6—O11 | 1.233 (7) |
C17—H17B | 0.9800 | O9—H9 | 0.8400 |
C17—H17C | 0.9800 | O12—H12 | 0.906 (14) |
C18—H18 | 0.9500 | C30—H30 | 1.0000 |
C18—N4 | 1.272 (6) | C30—Cl0A | 1.848 (19) |
C19—H19A | 0.9900 | C30—Cl1 | 1.71 (3) |
C19—H19B | 0.9900 | C30—Cl2 | 1.79 (2) |
C19—C20 | 1.490 (7) | C30A—H30A | 1.0000 |
C19—O7 | 1.433 (6) | C30A—Cl1A | 1.74 (2) |
C20—H20A | 0.9900 | C30A—Cl2A | 1.722 (18) |
C20—H20B | 0.9900 | C30A—Cl3 | 1.758 (16) |
| | | |
C2—C1—C6 | 118.5 (4) | C25—C24—C23 | 120.2 (5) |
O1—C1—C2 | 120.7 (4) | C25—C24—H24 | 119.9 |
O1—C1—C6 | 120.8 (4) | C24—C25—H25 | 120.8 |
C1—C2—H2 | 119.7 | C26—C25—C24 | 118.5 (5) |
C3—C2—C1 | 120.6 (4) | C26—C25—H25 | 120.8 |
C3—C2—H2 | 119.7 | C25—C26—C27 | 123.4 (5) |
C2—C3—H3 | 120.1 | C25—C26—N6 | 119.1 (5) |
C2—C3—C4 | 119.8 (4) | C27—C26—N6 | 117.5 (6) |
C4—C3—H3 | 120.1 | C22—C27—C26 | 117.4 (5) |
C3—C4—N1 | 119.8 (4) | C22—C27—H27 | 121.3 |
C5—C4—C3 | 121.7 (4) | C26—C27—H27 | 121.3 |
C5—C4—N1 | 118.5 (4) | H28A—C28—H28B | 109.5 |
C4—C5—H5 | 120.2 | H28A—C28—H28C | 109.5 |
C4—C5—C6 | 119.6 (4) | H28B—C28—H28C | 109.5 |
C6—C5—H5 | 120.2 | C29—C28—H28A | 109.5 |
C1—C6—C7 | 124.3 (4) | C29—C28—H28B | 109.5 |
C5—C6—C1 | 119.8 (4) | C29—C28—H28C | 109.5 |
C5—C6—C7 | 115.7 (4) | C28—C29—H29A | 108.3 |
C6—C7—H7 | 117.2 | C28—C29—H29B | 108.3 |
N2—C7—C6 | 125.6 (4) | C28—C29—O12 | 116.0 (7) |
N2—C7—H7 | 117.2 | H29A—C29—H29B | 107.4 |
H8A—C8—H8B | 108.2 | O12—C29—H29A | 108.3 |
C9—C8—H8A | 109.7 | O12—C29—H29B | 108.3 |
C9—C8—H8B | 109.7 | N2—Cu1—O12 | 103.70 (15) |
O4—C8—H8A | 109.7 | N3—Cu1—N2 | 100.05 (15) |
O4—C8—H8B | 109.7 | N3—Cu1—O1 | 169.97 (14) |
O4—C8—C9 | 109.7 (5) | N3—Cu1—O12 | 90.91 (16) |
C8—C9—H9A | 109.1 | O1—Cu1—N2 | 89.85 (13) |
C8—C9—H9B | 109.1 | O1—Cu1—O12 | 85.06 (13) |
H9A—C9—H9B | 107.8 | O6—Cu1—N2 | 159.56 (14) |
O5—C9—C8 | 112.6 (4) | O6—Cu1—N3 | 90.64 (14) |
O5—C9—H9A | 109.1 | O6—Cu1—O1 | 80.45 (11) |
O5—C9—H9B | 109.1 | O6—Cu1—O12 | 93.41 (13) |
C11—C10—H10 | 117.4 | Br2—Cu2—Br1 | 144.07 (3) |
N3—C10—H10 | 117.4 | N4—Cu2—Br1 | 91.63 (11) |
N3—C10—C11 | 125.1 (4) | N4—Cu2—Br2 | 91.86 (11) |
C12—C11—C10 | 123.6 (4) | N4—Cu2—O1 | 164.60 (13) |
C16—C11—C10 | 115.9 (4) | N4—Cu2—O6 | 88.83 (13) |
C16—C11—C12 | 120.5 (4) | O1—Cu2—Br1 | 93.70 (9) |
C11—C12—C13 | 117.5 (4) | O1—Cu2—Br2 | 92.27 (9) |
O6—C12—C11 | 122.2 (4) | O1—Cu2—O6 | 76.08 (11) |
O6—C12—C13 | 120.3 (4) | O6—Cu2—Br1 | 98.87 (9) |
C12—C13—C18 | 125.1 (4) | O6—Cu2—Br2 | 116.95 (9) |
C14—C13—C12 | 119.6 (4) | O2—N1—C4 | 118.3 (4) |
C14—C13—C18 | 115.3 (4) | O2—N1—O3 | 124.0 (4) |
C13—C14—H14 | 118.5 | O3—N1—C4 | 117.8 (4) |
C15—C14—C13 | 123.0 (4) | C7—N2—Cu1 | 125.4 (3) |
C15—C14—H14 | 118.5 | C7—N2—O4 | 109.8 (3) |
C14—C15—C17 | 121.1 (4) | O4—N2—Cu1 | 124.3 (3) |
C16—C15—C14 | 117.0 (4) | C10—N3—Cu1 | 127.6 (3) |
C16—C15—C17 | 122.0 (4) | C10—N3—O5 | 111.1 (3) |
C11—C16—H16 | 118.8 | O5—N3—Cu1 | 119.3 (3) |
C15—C16—C11 | 122.4 (4) | C18—N4—Cu2 | 127.5 (3) |
C15—C16—H16 | 118.8 | C18—N4—O7 | 110.6 (3) |
C15—C17—H17A | 109.5 | O7—N4—Cu2 | 121.6 (3) |
C15—C17—H17B | 109.5 | C21—N5—O8 | 108.7 (4) |
C15—C17—H17C | 109.5 | O10—N6—C26 | 118.2 (5) |
H17A—C17—H17B | 109.5 | O10—N6—O11 | 123.4 (6) |
H17A—C17—H17C | 109.5 | O11—N6—C26 | 118.4 (6) |
H17B—C17—H17C | 109.5 | C1—O1—Cu1 | 128.0 (3) |
C13—C18—H18 | 116.3 | C1—O1—Cu2 | 127.6 (3) |
N4—C18—C13 | 127.4 (4) | Cu1—O1—Cu2 | 103.44 (13) |
N4—C18—H18 | 116.3 | N2—O4—C8 | 112.7 (3) |
H19A—C19—H19B | 108.5 | N3—O5—C9 | 110.0 (4) |
C20—C19—H19A | 110.2 | C12—O6—Cu1 | 129.5 (3) |
C20—C19—H19B | 110.2 | C12—O6—Cu2 | 127.7 (2) |
O7—C19—H19A | 110.2 | Cu1—O6—Cu2 | 99.97 (12) |
O7—C19—H19B | 110.2 | N4—O7—C19 | 112.0 (3) |
O7—C19—C20 | 107.5 (4) | N5—O8—C20 | 109.1 (4) |
C19—C20—H20A | 110.1 | C23—O9—H9 | 109.5 |
C19—C20—H20B | 110.1 | C29—O12—Cu1 | 129.7 (4) |
H20A—C20—H20B | 108.4 | C29—O12—H12 | 102 (2) |
O8—C20—C19 | 108.1 (4) | Cu1—O12—H12 | 113 (2) |
O8—C20—H20A | 110.1 | Cl0A—C30—H30 | 114.0 |
O8—C20—H20B | 110.1 | Cl1—C30—H30 | 114.0 |
C22—C21—H21 | 119.3 | Cl1—C30—Cl0A | 102.4 (13) |
N5—C21—H21 | 119.3 | Cl1—C30—Cl2 | 106.3 (13) |
N5—C21—C22 | 121.3 (5) | Cl2—C30—H30 | 114.0 |
C23—C22—C21 | 118.3 (5) | Cl2—C30—Cl0A | 105.1 (13) |
C27—C22—C21 | 122.1 (5) | Cl1A—C30A—H30A | 110.3 |
C27—C22—C23 | 119.6 (5) | Cl1A—C30A—Cl3 | 103.5 (9) |
C24—C23—C22 | 120.9 (5) | Cl2A—C30A—H30A | 110.3 |
O9—C23—C22 | 117.3 (5) | Cl2A—C30A—Cl1A | 111.0 (10) |
O9—C23—C24 | 121.8 (5) | Cl2A—C30A—Cl3 | 111.2 (13) |
C23—C24—H24 | 119.9 | Cl3—C30A—H30A | 110.3 |