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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520621008441/lo5094sup1.cif
Contains datablocks 1, 2, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621008441/lo50941sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621008441/lo50942sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621008441/lo50943sup4.hkl
Contains datablock 3

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Portable Document Format (PDF) file https://doi.org/10.1107/S2052520621008441/lo5094sup5.pdf
Details of materials and instrumentation. Tables S1 and S2

CCDC references: 2052695; 2052696; 2052697

Computing details top

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).

(1) top
Crystal data top
C56H54Cu4N12O24·2(ClO4)·2(CH4O)F(000) = 1832
Mr = 1796.25Dx = 1.744 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 15.2568 (4) ÅCell parameters from 9913 reflections
b = 14.5155 (4) Åθ = 2.4–26.7°
c = 15.4550 (4) ŵ = 1.41 mm1
β = 92.086 (1)°T = 173 K
V = 3420.40 (16) Å3BLOCK
Z = 20.24 × 0.22 × 0.19 mm
Data collection top
Bruker D8 Venture
diffractometer
6759 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
phi and ω scansθmax = 26.7°, θmin = 2.3°
Absorption correction: multi-scan
SADABS
h = 1919
Tmin = 0.659, Tmax = 0.745k = 1818
43196 measured reflectionsl = 1917
7259 independent reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.036H 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 reflectionsΔρmax = 1.76 e Å3
530 parametersΔρmin = 0.84 e Å3
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
xyzUiso*/UeqOcc. (<1)
Cu10.91994 (2)0.42705 (2)0.47503 (2)0.02062 (8)
Cu20.81008 (2)0.54391 (2)0.32847 (2)0.02363 (8)
O10.99904 (11)0.50320 (11)0.40949 (10)0.0237 (3)
O21.1402 (2)0.4285 (2)0.04653 (15)0.0771 (9)
O31.16494 (17)0.2965 (2)0.10245 (15)0.0596 (7)
O41.01646 (12)0.26020 (12)0.53252 (11)0.0319 (4)
O50.84267 (13)0.27639 (12)0.58260 (11)0.0326 (4)
O60.82819 (11)0.51845 (11)0.45155 (10)0.0234 (3)
O70.82668 (13)0.75794 (13)0.31108 (12)0.0368 (4)
O80.76207 (13)0.64490 (14)0.17251 (12)0.0362 (4)
O90.84128 (12)0.41440 (12)0.31032 (11)0.0289 (4)
O100.98332 (17)0.2922 (2)0.04492 (18)0.0700 (8)
O111.0022 (2)0.1669 (2)0.0280 (2)0.0813 (10)
O120.66230 (13)0.52197 (16)0.33764 (13)0.0429 (5)
H120.6317 (12)0.519 (2)0.2890 (9)0.064*
N11.14247 (17)0.3761 (2)0.10805 (15)0.0464 (7)
N21.00387 (13)0.32580 (14)0.46466 (12)0.0241 (4)
N30.83437 (13)0.36773 (13)0.55317 (13)0.0239 (4)
N40.80778 (14)0.68020 (14)0.36246 (13)0.0266 (4)
N50.80502 (15)0.56364 (16)0.20435 (13)0.0308 (5)
N60.97630 (18)0.2464 (2)0.0207 (2)0.0582 (8)
C11.03816 (15)0.47239 (17)0.34105 (14)0.0225 (4)
C21.06584 (15)0.37967 (17)0.33332 (15)0.0238 (5)
C31.10456 (16)0.34945 (19)0.25788 (16)0.0295 (5)
H31.12490.28790.25310.035*
C41.11278 (16)0.4105 (2)0.19058 (15)0.0325 (6)
C51.09085 (17)0.5031 (2)0.19807 (16)0.0339 (6)
H51.09980.54440.15150.041*
C61.05612 (16)0.53422 (19)0.27343 (16)0.0290 (5)
H61.04410.59800.28010.035*
C71.05748 (15)0.31437 (17)0.40359 (15)0.0255 (5)
H71.09330.26080.40440.031*
C80.95615 (19)0.18486 (18)0.52274 (19)0.0357 (6)
H8A0.96280.14410.57390.043*
H8B0.97120.14850.47110.043*
C90.86210 (18)0.21537 (18)0.51311 (18)0.0329 (6)
H9A0.85220.24730.45700.039*
H9B0.82290.16110.51410.039*
C100.77784 (16)0.41121 (17)0.59732 (15)0.0267 (5)
H100.74880.37800.64080.032*
C110.75547 (15)0.50714 (17)0.58532 (15)0.0251 (5)
C120.78022 (15)0.55751 (16)0.51221 (15)0.0226 (4)
C130.75395 (15)0.65006 (17)0.50536 (15)0.0257 (5)
C140.70756 (17)0.69077 (18)0.57170 (16)0.0308 (5)
H140.69310.75430.56750.037*
C150.68193 (18)0.6416 (2)0.64357 (17)0.0337 (6)
C160.70581 (17)0.54948 (19)0.64842 (16)0.0312 (5)
H160.68780.51390.69620.037*
C170.6318 (2)0.6874 (2)0.7139 (2)0.0503 (8)
H17A0.67300.71010.75910.076*
H17B0.59170.64280.73900.076*
H17C0.59790.73920.68940.076*
C180.77861 (16)0.70874 (17)0.43431 (16)0.0275 (5)
H180.77260.77340.44170.033*
C190.88018 (18)0.7363 (2)0.24016 (19)0.0384 (6)
H19A0.91650.68150.25470.046*
H19B0.92010.78840.22940.046*
C200.8249 (2)0.7173 (2)0.15990 (19)0.0418 (7)
H20A0.79340.77420.14220.050*
H20B0.86350.69960.11250.050*
C210.83001 (18)0.5104 (2)0.14403 (16)0.0352 (6)
H210.82380.53190.08610.042*
C220.86678 (17)0.4204 (2)0.15805 (17)0.0328 (6)
C230.86576 (16)0.37506 (18)0.23964 (16)0.0288 (5)
C240.89341 (18)0.28137 (19)0.24222 (19)0.0356 (6)
H240.88770.24700.29410.043*
C250.92804 (19)0.2396 (2)0.1715 (2)0.0429 (7)
H250.94750.17750.17500.051*
C260.93441 (18)0.2888 (2)0.0946 (2)0.0432 (7)
C270.90222 (18)0.3760 (2)0.08640 (18)0.0403 (7)
H270.90370.40680.03220.048*
C280.6151 (2)0.4694 (2)0.3978 (2)0.0492 (8)
H28A0.56200.44430.36900.074*
H28B0.59870.50890.44600.074*
H28C0.65190.41870.41990.074*
Cl10.33320 (6)0.56949 (6)0.12328 (6)0.0574 (2)
O130.5620 (4)0.4776 (6)0.1930 (4)0.0611 (19)0.547 (15)
H130.51550.50840.18820.092*0.547 (15)
O13A0.5677 (6)0.5340 (13)0.1909 (6)0.095 (4)0.453 (15)
H13A0.51930.55630.17390.143*0.453 (15)
O140.4164 (6)0.6041 (7)0.1665 (8)0.091 (3)0.547 (15)
O14A0.4202 (6)0.5912 (10)0.1198 (11)0.101 (4)0.453 (15)
O150.3299 (8)0.6125 (6)0.0459 (4)0.074 (3)0.547 (15)
O15A0.2779 (9)0.5877 (6)0.0419 (5)0.081 (3)0.453 (15)
O160.3268 (2)0.47310 (17)0.13361 (18)0.0745 (9)
O170.2807 (3)0.6142 (2)0.1861 (2)0.0921 (11)
C290.6033 (3)0.4814 (3)0.1205 (3)0.0741 (12)
H29A0.56220.46800.07190.111*0.547 (15)
H29B0.65070.43590.12170.111*0.547 (15)
H29C0.62800.54320.11340.111*0.547 (15)
H29D0.56100.48080.07130.111*0.453 (15)
H29E0.61490.41810.13980.111*0.453 (15)
H29F0.65810.50990.10290.111*0.453 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02309 (14)0.02021 (14)0.01900 (14)0.00196 (10)0.00665 (10)0.00251 (10)
Cu20.02706 (15)0.02623 (15)0.01779 (14)0.00225 (11)0.00347 (11)0.00262 (11)
O10.0279 (8)0.0235 (8)0.0201 (7)0.0011 (6)0.0084 (6)0.0002 (6)
O20.102 (2)0.107 (2)0.0236 (11)0.0061 (18)0.0272 (13)0.0058 (13)
O30.0575 (15)0.0799 (19)0.0425 (13)0.0120 (13)0.0197 (11)0.0205 (12)
O40.0345 (9)0.0309 (9)0.0304 (9)0.0043 (7)0.0020 (7)0.0136 (7)
O50.0458 (11)0.0240 (9)0.0291 (9)0.0049 (8)0.0159 (8)0.0082 (7)
O60.0264 (8)0.0260 (8)0.0181 (7)0.0047 (7)0.0059 (6)0.0024 (6)
O70.0501 (12)0.0258 (9)0.0348 (10)0.0026 (8)0.0049 (8)0.0107 (8)
O80.0383 (10)0.0411 (11)0.0291 (9)0.0041 (8)0.0004 (8)0.0109 (8)
O90.0344 (9)0.0287 (9)0.0240 (8)0.0003 (7)0.0044 (7)0.0019 (7)
O100.0537 (15)0.108 (2)0.0501 (15)0.0144 (15)0.0230 (12)0.0359 (16)
O110.0686 (18)0.079 (2)0.098 (2)0.0049 (15)0.0267 (16)0.0525 (18)
O120.0349 (11)0.0584 (13)0.0353 (11)0.0004 (9)0.0018 (8)0.0060 (10)
N10.0354 (13)0.079 (2)0.0259 (12)0.0005 (13)0.0115 (10)0.0095 (13)
N20.0274 (10)0.0231 (10)0.0221 (9)0.0013 (8)0.0037 (8)0.0044 (8)
N30.0277 (10)0.0195 (9)0.0247 (10)0.0010 (8)0.0054 (8)0.0050 (8)
N40.0294 (10)0.0246 (10)0.0258 (10)0.0009 (8)0.0002 (8)0.0078 (8)
N50.0328 (11)0.0367 (12)0.0231 (10)0.0028 (9)0.0039 (8)0.0060 (9)
N60.0394 (15)0.078 (2)0.0582 (19)0.0093 (15)0.0135 (13)0.0406 (17)
C10.0200 (10)0.0304 (12)0.0172 (10)0.0014 (9)0.0016 (8)0.0006 (9)
C20.0208 (11)0.0296 (12)0.0212 (11)0.0010 (9)0.0032 (9)0.0027 (9)
C30.0227 (11)0.0378 (14)0.0284 (12)0.0002 (10)0.0049 (9)0.0074 (10)
C40.0244 (12)0.0555 (17)0.0182 (11)0.0026 (11)0.0075 (9)0.0051 (11)
C50.0289 (13)0.0531 (17)0.0201 (11)0.0028 (12)0.0053 (10)0.0089 (11)
C60.0260 (12)0.0355 (13)0.0259 (12)0.0005 (10)0.0038 (9)0.0065 (10)
C70.0238 (11)0.0252 (11)0.0276 (12)0.0019 (9)0.0026 (9)0.0028 (9)
C80.0429 (15)0.0238 (12)0.0414 (15)0.0041 (11)0.0132 (12)0.0062 (11)
C90.0385 (14)0.0241 (12)0.0368 (14)0.0045 (10)0.0117 (11)0.0004 (10)
C100.0281 (12)0.0300 (12)0.0225 (11)0.0010 (10)0.0078 (9)0.0037 (9)
C110.0239 (11)0.0290 (12)0.0227 (11)0.0034 (9)0.0041 (9)0.0005 (9)
C120.0205 (11)0.0271 (12)0.0202 (11)0.0021 (9)0.0016 (8)0.0020 (9)
C130.0254 (11)0.0285 (12)0.0231 (11)0.0030 (9)0.0010 (9)0.0010 (9)
C140.0330 (13)0.0301 (13)0.0294 (12)0.0089 (10)0.0001 (10)0.0046 (10)
C150.0336 (13)0.0422 (15)0.0254 (12)0.0118 (11)0.0043 (10)0.0053 (11)
C160.0322 (13)0.0400 (14)0.0218 (11)0.0064 (11)0.0070 (10)0.0015 (10)
C170.064 (2)0.0543 (19)0.0338 (15)0.0271 (16)0.0167 (14)0.0030 (14)
C180.0283 (12)0.0235 (11)0.0306 (12)0.0032 (9)0.0032 (10)0.0004 (10)
C190.0300 (13)0.0437 (16)0.0419 (15)0.0029 (12)0.0068 (11)0.0173 (13)
C200.0458 (16)0.0469 (17)0.0335 (14)0.0026 (13)0.0092 (12)0.0173 (13)
C210.0345 (14)0.0509 (16)0.0205 (12)0.0029 (12)0.0058 (10)0.0022 (11)
C220.0287 (13)0.0438 (15)0.0262 (12)0.0050 (11)0.0057 (10)0.0069 (11)
C230.0229 (11)0.0354 (13)0.0283 (12)0.0039 (10)0.0030 (9)0.0064 (10)
C240.0317 (13)0.0338 (14)0.0413 (15)0.0045 (11)0.0021 (11)0.0099 (12)
C250.0321 (14)0.0410 (16)0.0557 (18)0.0038 (12)0.0027 (13)0.0212 (14)
C260.0293 (13)0.0570 (19)0.0439 (16)0.0078 (13)0.0088 (12)0.0281 (15)
C270.0335 (14)0.0584 (19)0.0296 (13)0.0092 (13)0.0080 (11)0.0135 (13)
C280.0446 (17)0.0513 (19)0.0523 (19)0.0155 (14)0.0078 (14)0.0079 (15)
Cl10.0605 (5)0.0420 (4)0.0715 (6)0.0092 (4)0.0254 (4)0.0297 (4)
O130.056 (3)0.067 (4)0.059 (3)0.011 (3)0.015 (2)0.017 (3)
O13A0.065 (5)0.160 (10)0.060 (4)0.001 (6)0.013 (3)0.016 (6)
O140.100 (5)0.069 (4)0.107 (7)0.003 (4)0.030 (5)0.025 (5)
O14A0.060 (4)0.107 (7)0.138 (9)0.003 (4)0.050 (6)0.066 (7)
O150.106 (7)0.062 (4)0.055 (3)0.003 (4)0.010 (4)0.023 (3)
O15A0.111 (8)0.053 (4)0.077 (5)0.014 (4)0.032 (5)0.028 (3)
O160.126 (3)0.0364 (13)0.0611 (17)0.0134 (15)0.0021 (17)0.0067 (12)
O170.123 (3)0.073 (2)0.083 (2)0.034 (2)0.045 (2)0.0097 (17)
C290.068 (3)0.063 (3)0.090 (3)0.010 (2)0.017 (2)0.004 (2)
Geometric parameters (Å, º) top
Cu1—O11.9477 (16)C10—C111.444 (3)
Cu1—O1i2.3618 (17)C11—C121.409 (3)
Cu1—O61.9530 (16)C11—C161.399 (3)
Cu1—N21.960 (2)C12—C131.405 (3)
Cu1—N32.0048 (19)C13—C141.398 (3)
Cu2—O61.9476 (16)C13—C181.450 (3)
Cu2—O91.9618 (18)C14—H140.9500
Cu2—O122.286 (2)C14—C151.388 (4)
Cu2—N42.048 (2)C15—C161.388 (4)
Cu2—N51.938 (2)C15—C171.507 (4)
O1—Cu1i2.3618 (17)C16—H160.9500
O1—C11.312 (3)C17—H17A0.9800
O2—N11.217 (4)C17—H17B0.9800
O3—N11.209 (4)C17—H17C0.9800
O4—N21.424 (2)C18—H180.9500
O4—C81.434 (3)C19—H19A0.9900
O5—N31.406 (2)C19—H19B0.9900
O5—C91.431 (3)C19—C201.500 (4)
O6—C121.336 (3)C20—H20A0.9900
O7—N41.415 (3)C20—H20B0.9900
O7—C191.425 (3)C21—H210.9500
O8—N51.428 (3)C21—C221.435 (4)
O8—C201.440 (4)C22—C231.423 (4)
O9—C231.299 (3)C22—C271.407 (4)
O10—N61.220 (4)C23—C241.424 (4)
O11—N61.223 (5)C24—H240.9500
O12—H120.872 (9)C24—C251.372 (4)
O12—C281.419 (4)C25—H250.9500
N1—C41.457 (3)C25—C261.393 (5)
N2—C71.282 (3)C26—C271.362 (5)
N3—C101.285 (3)C27—H270.9500
N4—C181.280 (3)C28—H28A0.9800
N5—C211.279 (3)C28—H28B0.9800
N6—C261.465 (4)C28—H28C0.9800
C1—C21.417 (3)Cl1—O141.500 (9)
C1—C61.412 (3)Cl1—O14A1.368 (9)
C2—C31.397 (3)Cl1—O151.348 (5)
C2—C71.451 (3)Cl1—O15A1.512 (8)
C3—H30.9500Cl1—O161.412 (3)
C3—C41.375 (4)Cl1—O171.436 (3)
C4—C51.391 (4)O13—H130.8401
C5—H50.9500O13—C291.307 (8)
C5—C61.373 (4)O13A—H13A0.8400
C6—H60.9500O13A—C291.451 (11)
C7—H70.9500C29—H29A0.9800
C8—H8A0.9900C29—H29B0.9800
C8—H8B0.9900C29—H29C0.9800
C8—C91.504 (4)C29—H29D0.9800
C9—H9A0.9900C29—H29E0.9800
C9—H9B0.9900C29—H29F0.9800
C10—H100.9500
O1—Cu1—O1i80.36 (6)C16—C11—C12119.9 (2)
O1—Cu1—O688.36 (7)O6—C12—C11120.8 (2)
O1—Cu1—N287.94 (7)O6—C12—C13121.0 (2)
O1—Cu1—N3170.57 (7)C13—C12—C11118.2 (2)
O6—Cu1—O1i101.60 (6)C12—C13—C18122.5 (2)
O6—Cu1—N2163.80 (8)C14—C13—C12120.0 (2)
O6—Cu1—N385.73 (7)C14—C13—C18117.3 (2)
N2—Cu1—O1i93.31 (7)C13—C14—H14118.8
N2—Cu1—N399.73 (8)C15—C14—C13122.3 (2)
N3—Cu1—O1i93.63 (7)C15—C14—H14118.8
O6—Cu2—O986.06 (7)C14—C15—C17121.1 (3)
O6—Cu2—O1291.04 (7)C16—C15—C14117.2 (2)
O6—Cu2—N486.32 (7)C16—C15—C17121.7 (3)
O9—Cu2—O1296.91 (8)C11—C16—H16118.9
O9—Cu2—N4165.70 (8)C15—C16—C11122.2 (2)
N4—Cu2—O1295.31 (8)C15—C16—H16118.9
N5—Cu2—O6173.61 (8)C15—C17—H17A109.5
N5—Cu2—O990.07 (8)C15—C17—H17B109.5
N5—Cu2—O1294.48 (8)C15—C17—H17C109.5
N5—Cu2—N496.36 (9)H17A—C17—H17B109.5
Cu1—O1—Cu1i99.64 (6)H17A—C17—H17C109.5
C1—O1—Cu1122.31 (15)H17B—C17—H17C109.5
C1—O1—Cu1i120.97 (14)N4—C18—C13125.1 (2)
N2—O4—C8111.31 (19)N4—C18—H18117.5
N3—O5—C9111.07 (17)C13—C18—H18117.5
Cu2—O6—Cu1112.68 (8)O7—C19—H19A109.5
C12—O6—Cu1124.40 (14)O7—C19—H19B109.5
C12—O6—Cu2122.88 (14)O7—C19—C20110.8 (2)
N4—O7—C19112.9 (2)H19A—C19—H19B108.1
N5—O8—C20110.5 (2)C20—C19—H19A109.5
C23—O9—Cu2128.31 (17)C20—C19—H19B109.5
Cu2—O12—H12116.9 (13)O8—C20—C19112.3 (2)
C28—O12—Cu2129.85 (19)O8—C20—H20A109.1
C28—O12—H12105.4 (14)O8—C20—H20B109.1
O2—N1—C4118.0 (3)C19—C20—H20A109.1
O3—N1—O2122.8 (3)C19—C20—H20B109.1
O3—N1—C4119.2 (3)H20A—C20—H20B107.9
O4—N2—Cu1120.80 (14)N5—C21—H21117.8
C7—N2—Cu1126.41 (17)N5—C21—C22124.4 (2)
C7—N2—O4112.52 (19)C22—C21—H21117.8
O5—N3—Cu1123.16 (14)C23—C22—C21122.6 (2)
C10—N3—Cu1124.99 (17)C27—C22—C21117.3 (3)
C10—N3—O5110.23 (18)C27—C22—C23120.2 (3)
O7—N4—Cu2128.35 (15)O9—C23—C22123.7 (2)
C18—N4—Cu2123.03 (17)O9—C23—C24119.3 (2)
C18—N4—O7108.2 (2)C22—C23—C24117.0 (2)
O8—N5—Cu2117.66 (15)C23—C24—H24119.3
C21—N5—Cu2129.0 (2)C25—C24—C23121.5 (3)
C21—N5—O8113.1 (2)C25—C24—H24119.3
O10—N6—O11123.5 (3)C24—C25—H25120.2
O10—N6—C26118.3 (3)C24—C25—C26119.5 (3)
O11—N6—C26118.2 (4)C26—C25—H25120.2
O1—C1—C2122.5 (2)C25—C26—N6119.7 (3)
O1—C1—C6119.1 (2)C27—C26—N6118.9 (3)
C6—C1—C2118.3 (2)C27—C26—C25121.4 (3)
C1—C2—C7121.5 (2)C22—C27—H27120.0
C3—C2—C1120.3 (2)C26—C27—C22120.0 (3)
C3—C2—C7118.1 (2)C26—C27—H27120.0
C2—C3—H3120.6O12—C28—H28A109.5
C4—C3—C2118.8 (2)O12—C28—H28B109.5
C4—C3—H3120.6O12—C28—H28C109.5
C3—C4—N1118.8 (3)H28A—C28—H28B109.5
C3—C4—C5122.0 (2)H28A—C28—H28C109.5
C5—C4—N1119.1 (2)H28B—C28—H28C109.5
C4—C5—H5120.3O14A—Cl1—O15A116.1 (6)
C6—C5—C4119.3 (2)O14A—Cl1—O16107.7 (6)
C6—C5—H5120.3O14A—Cl1—O17119.2 (8)
C1—C6—H6119.7O15—Cl1—O14104.0 (5)
C5—C6—C1120.7 (2)O15—Cl1—O16124.0 (4)
C5—C6—H6119.7O15—Cl1—O17112.8 (3)
N2—C7—C2122.9 (2)O16—Cl1—O14110.0 (4)
N2—C7—H7118.6O16—Cl1—O15A103.2 (4)
C2—C7—H7118.6O16—Cl1—O17109.19 (19)
O4—C8—H8A109.0O17—Cl1—O1491.8 (5)
O4—C8—H8B109.0O17—Cl1—O15A100.1 (5)
O4—C8—C9113.1 (2)C29—O13—H13109.5
H8A—C8—H8B107.8C29—O13A—H13A108.4
C9—C8—H8A109.0O13—C29—H29A109.5
C9—C8—H8B109.0O13—C29—H29B109.5
O5—C9—C8109.3 (2)O13—C29—H29C109.5
O5—C9—H9A109.8O13A—C29—H29D109.5
O5—C9—H9B109.8O13A—C29—H29E109.5
C8—C9—H9A109.8O13A—C29—H29F109.5
C8—C9—H9B109.8H29A—C29—H29B109.5
H9A—C9—H9B108.3H29A—C29—H29C109.5
N3—C10—H10117.8H29B—C29—H29C109.5
N3—C10—C11124.4 (2)H29D—C29—H29E109.5
C11—C10—H10117.8H29D—C29—H29F109.5
C12—C11—C10122.3 (2)H29E—C29—H29F109.5
C16—C11—C10117.7 (2)
Cu1i—O1—C1—C293.6 (2)C1—C2—C7—N220.9 (4)
Cu1—O1—C1—C234.1 (3)C2—C1—C6—C57.0 (4)
Cu1i—O1—C1—C684.4 (2)C2—C3—C4—N1172.1 (2)
Cu1—O1—C1—C6148.02 (18)C2—C3—C4—C55.7 (4)
Cu1—O6—C12—C1135.1 (3)C3—C2—C7—N2160.9 (2)
Cu1—O6—C12—C13144.14 (18)C3—C4—C5—C63.0 (4)
Cu1—N2—C7—C22.8 (3)C4—C5—C6—C13.5 (4)
Cu1—N3—C10—C1112.4 (4)C6—C1—C2—C34.2 (3)
Cu2—O6—C12—C11142.36 (18)C6—C1—C2—C7173.9 (2)
Cu2—O6—C12—C1338.4 (3)C7—C2—C3—C4179.8 (2)
Cu2—O9—C23—C225.8 (4)C8—O4—N2—Cu188.3 (2)
Cu2—O9—C23—C24174.20 (17)C8—O4—N2—C797.3 (2)
Cu2—N4—C18—C138.2 (3)C9—O5—N3—Cu146.3 (2)
Cu2—N5—C21—C221.4 (4)C9—O5—N3—C10147.6 (2)
O1—C1—C2—C3177.8 (2)C10—C11—C12—O61.9 (4)
O1—C1—C2—C74.0 (3)C10—C11—C12—C13178.8 (2)
O1—C1—C6—C5175.0 (2)C10—C11—C16—C15179.1 (2)
O2—N1—C4—C3172.0 (3)C11—C12—C13—C142.5 (3)
O2—N1—C4—C55.8 (4)C11—C12—C13—C18177.8 (2)
O3—N1—C4—C35.1 (4)C12—C11—C16—C152.3 (4)
O3—N1—C4—C5177.0 (3)C12—C13—C14—C153.4 (4)
O4—N2—C7—C2171.3 (2)C12—C13—C18—N416.9 (4)
O4—C8—C9—O552.3 (3)C13—C14—C15—C161.3 (4)
O5—N3—C10—C11178.2 (2)C13—C14—C15—C17179.8 (3)
O6—C12—C13—C14176.8 (2)C14—C13—C18—N4167.7 (2)
O6—C12—C13—C181.5 (4)C14—C15—C16—C111.5 (4)
O7—N4—C18—C13178.3 (2)C16—C11—C12—O6179.5 (2)
O7—C19—C20—O856.2 (3)C16—C11—C12—C130.2 (3)
O8—N5—C21—C22173.5 (2)C17—C15—C16—C11177.3 (3)
O9—C23—C24—C25173.4 (2)C18—C13—C14—C15178.9 (2)
O10—N6—C26—C25177.8 (3)C19—O7—N4—Cu222.4 (3)
O10—N6—C26—C272.3 (4)C19—O7—N4—C18164.6 (2)
O11—N6—C26—C252.3 (4)C20—O8—N5—Cu295.3 (2)
O11—N6—C26—C27177.5 (3)C20—O8—N5—C2189.1 (3)
N1—C4—C5—C6174.8 (2)C21—C22—C23—O98.3 (4)
N2—O4—C8—C953.1 (3)C21—C22—C23—C24171.7 (2)
N3—O5—C9—C8107.5 (2)C21—C22—C27—C26177.0 (3)
N3—C10—C11—C1213.4 (4)C22—C23—C24—C256.6 (4)
N3—C10—C11—C16168.0 (2)C23—C22—C27—C261.0 (4)
N4—O7—C19—C2093.9 (3)C23—C24—C25—C261.7 (4)
N5—O8—C20—C1954.5 (3)C24—C25—C26—N6176.2 (3)
N5—C21—C22—C2310.7 (4)C24—C25—C26—C273.9 (4)
N5—C21—C22—C27171.3 (3)C25—C26—C27—C224.2 (4)
N6—C26—C27—C22175.9 (2)C27—C22—C23—O9173.8 (2)
C1—C2—C3—C42.0 (4)C27—C22—C23—C246.2 (4)
Symmetry code: (i) x+2, y+1, z+1.
(2) top
Crystal data top
C58H58Cu4N12O24·2(NO3)·2(C2H6O)F(000) = 1824
Mr = 1777.48Dx = 1.690 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 15.1553 (6) ÅCell parameters from 3115 reflections
b = 15.2135 (6) Åθ = 2.1–25.2°
c = 15.1959 (6) ŵ = 1.31 mm1
β = 94.292 (1)°T = 173 K
V = 3493.8 (2) Å3Block
Z = 20.17 × 0.14 × 0.13 mm
Data collection top
Bruker D8 Venture
diffractometer
Rint = 0.044
Absorption correction: multi-scanθmax = 26.8°, θmin = 2.3°
Tmin = 0.81, Tmax = 0.85h = 1919
35111 measured reflectionsk = 1919
7413 independent reflectionsl = 1919
5276 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.052H-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 reflectionsΔρmax = 0.23 e Å3
509 parametersΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
C10.33791 (18)0.5227 (2)1.03790 (19)0.0335 (7)
C20.32845 (19)0.6117 (2)1.06068 (19)0.0340 (7)
C30.25315 (19)0.6403 (2)1.10234 (18)0.0380 (7)
H30.2453370.7003761.1168290.046*
C40.19249 (19)0.5787 (2)1.12082 (19)0.0371 (7)
C50.20186 (18)0.4897 (2)1.10392 (18)0.0342 (7)
H50.1592700.4484671.1209780.041*
C60.2745 (2)0.4627 (2)1.0618 (2)0.0377 (7)
H60.2814830.4021591.0487740.045*
C70.3959 (2)0.6771 (2)1.0472 (2)0.0400 (8)
H70.3931230.7316931.0772100.048*
C80.5085 (2)0.8015 (2)0.9450 (2)0.0379 (7)
H8A0.5580210.8439990.9511810.045*
H8B0.4538310.8326760.9588620.045*
C90.49813 (19)0.76860 (19)0.8513 (2)0.0380 (7)
H9A0.4423660.7348710.8418370.046*
H9B0.4950730.8191180.8100940.046*
C100.58975 (19)0.5846 (2)0.7724 (2)0.0358 (7)
H100.6300500.6181990.7412270.043*
C110.58350 (19)0.4919 (2)0.75353 (19)0.0360 (7)
C120.51482 (19)0.43971 (19)0.78010 (19)0.0328 (6)
C130.51294 (19)0.3513 (2)0.75695 (19)0.0379 (8)
C140.5808 (2)0.3159 (2)0.7100 (2)0.0396 (8)
H140.5794970.2551250.6955500.048*
C150.65043 (19)0.3682 (2)0.68396 (19)0.0375 (7)
C160.64744 (19)0.4567 (2)0.7040 (2)0.0355 (7)
H160.6909700.4945910.6828740.043*
C170.7222 (2)0.3281 (2)0.6334 (2)0.0455 (8)
H17A0.7646950.3737690.6195990.068*
H17B0.6959450.3022790.5785060.068*
H17C0.7527720.2822890.6693290.068*
C180.44666 (19)0.2905 (2)0.78443 (19)0.0356 (7)
H180.4579870.2294940.7785240.043*
C190.26186 (19)0.2536 (2)0.89600 (19)0.0379 (7)
H19A0.2766460.3079070.9298110.045*
H19B0.2589490.2045070.9384720.045*
C200.17413 (19)0.2642 (2)0.8456 (2)0.0415 (8)
H20A0.1570100.2076520.8168840.050*
H20B0.1290960.2787480.8872460.050*
C210.1416 (2)0.4602 (2)0.8401 (2)0.0380 (8)
H210.0840540.4351740.8384430.046*
C220.15151 (19)0.5496 (2)0.86787 (19)0.0366 (7)
C230.2306 (2)0.5988 (2)0.85973 (19)0.0361 (7)
C240.22802 (19)0.6905 (2)0.8787 (2)0.0374 (7)
H240.2771820.7265190.8677300.045*
C250.15494 (19)0.7272 (2)0.91294 (19)0.0381 (7)
H250.1544350.7881970.9264900.046*
C260.0827 (2)0.6761 (2)0.9275 (2)0.0419 (8)
C270.0784 (2)0.5907 (2)0.9026 (2)0.0390 (8)
H270.0256170.5582200.9085580.047*
C280.3976 (3)0.5074 (2)0.5471 (2)0.0626 (11)
H28A0.4424540.4612240.5564560.094*
H28B0.4253230.5608990.5261520.094*
H28C0.3513760.4877100.5029340.094*
C290.3589 (2)0.5255 (2)0.6292 (2)0.0469 (9)
H29A0.3088770.5669530.6183880.056*
H29B0.4035590.5535640.6710060.056*
C300.0982 (2)0.5265 (2)0.6231 (2)0.0500 (9)
H30A0.0643780.4789500.6482420.075*
H30B0.0598510.5778280.6122500.075*
H30C0.1482650.5423430.6646430.075*
C310.1323 (2)0.4961 (2)0.5370 (2)0.0482 (9)
H31A0.0820690.4837340.4932800.058*
H31B0.1693570.5425250.5128080.058*
Cu10.47140 (2)0.56651 (2)0.91649 (2)0.03352 (11)
Cu20.32899 (2)0.43912 (2)0.81502 (2)0.03459 (11)
N10.11334 (17)0.6093 (2)1.16244 (17)0.0427 (7)
N20.45940 (15)0.66496 (15)0.99640 (16)0.0343 (6)
N30.54430 (15)0.62579 (15)0.82910 (16)0.0341 (6)
N40.37470 (16)0.31276 (15)0.81575 (16)0.0352 (6)
N50.20406 (16)0.41196 (16)0.81750 (16)0.0382 (6)
N60.00632 (17)0.71417 (19)0.96823 (17)0.0423 (7)
N70.1785 (2)0.36510 (18)0.3330 (2)0.0481 (7)
O10.40638 (12)0.49447 (12)0.99615 (12)0.0341 (5)
O20.06763 (15)0.55226 (16)1.19597 (16)0.0539 (6)
O30.09506 (15)0.68610 (16)1.16139 (15)0.0521 (6)
O40.52541 (13)0.73042 (13)1.00717 (13)0.0389 (5)
O50.57089 (13)0.71405 (13)0.83391 (13)0.0387 (5)
O60.45305 (12)0.47279 (13)0.82991 (13)0.0360 (5)
O70.32853 (13)0.23625 (13)0.83797 (14)0.0403 (5)
O80.17448 (13)0.33125 (13)0.77977 (14)0.0399 (5)
O90.30322 (13)0.56362 (12)0.83457 (13)0.0350 (5)
O100.05610 (15)0.66677 (15)0.98053 (15)0.0505 (6)
O110.00997 (14)0.79181 (15)0.98864 (14)0.0492 (6)
O120.32757 (13)0.44537 (13)0.66761 (13)0.0392 (5)
H12B0.2659830.4354940.6431340.047*
O130.18392 (14)0.41751 (14)0.55423 (14)0.0448 (6)
H130.1993780.3970150.5064070.067*
O140.23843 (15)0.37232 (16)0.39305 (15)0.0544 (6)
O150.19887 (15)0.35885 (16)0.25515 (16)0.0574 (6)
O160.09853 (15)0.36182 (14)0.34977 (14)0.0484 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0226 (15)0.047 (2)0.0299 (17)0.0073 (14)0.0047 (14)0.0050 (14)
C20.0302 (16)0.044 (2)0.0276 (16)0.0030 (14)0.0025 (13)0.0045 (14)
C30.0373 (17)0.049 (2)0.0279 (17)0.0046 (15)0.0048 (14)0.0052 (14)
C40.0294 (16)0.0549 (15)0.0280 (16)0.0111 (15)0.0081 (14)0.0057 (14)
C50.0265 (15)0.0457 (14)0.0311 (16)0.0080 (13)0.0071 (14)0.0083 (13)
C60.0375 (18)0.0415 (19)0.0346 (18)0.0036 (14)0.0053 (15)0.0081 (14)
C70.0369 (18)0.043 (2)0.0395 (19)0.0030 (14)0.0017 (16)0.0010 (14)
C80.0378 (17)0.0352 (18)0.0412 (18)0.0070 (14)0.0059 (15)0.0007 (14)
C90.0376 (17)0.0370 (18)0.0394 (18)0.0044 (14)0.0033 (15)0.0099 (14)
C100.0271 (15)0.043 (2)0.0372 (18)0.0059 (13)0.0029 (14)0.0097 (14)
C110.0336 (16)0.045 (2)0.0295 (17)0.0058 (12)0.0054 (14)0.0052 (14)
C120.0306 (15)0.0400 (18)0.0268 (15)0.0039 (12)0.0057 (13)0.0068 (13)
C130.0294 (16)0.049 (2)0.0334 (17)0.0023 (14)0.0108 (14)0.0084 (15)
C140.0363 (17)0.0437 (19)0.0367 (18)0.0131 (15)0.0120 (15)0.0093 (14)
C150.0316 (16)0.051 (2)0.0306 (17)0.0103 (14)0.0095 (14)0.0095 (14)
C160.0295 (16)0.043 (2)0.0358 (17)0.0027 (13)0.0117 (14)0.0035 (14)
C170.0403 (18)0.052 (2)0.046 (2)0.0071 (15)0.0139 (16)0.0120 (16)
C180.0309 (16)0.0388 (18)0.0354 (17)0.0062 (14)0.0084 (14)0.0106 (14)
C190.0397 (18)0.0437 (19)0.0312 (17)0.0146 (14)0.0098 (15)0.0102 (14)
C200.0349 (17)0.0394 (19)0.052 (2)0.0105 (14)0.0163 (16)0.0082 (16)
C210.0309 (17)0.045 (2)0.0385 (18)0.0079 (14)0.0074 (15)0.0074 (14)
C220.0348 (17)0.044 (2)0.0323 (17)0.0086 (14)0.0068 (14)0.0060 (14)
C230.0341 (17)0.0450 (19)0.0290 (17)0.0025 (15)0.0018 (14)0.0084 (14)
C240.0321 (17)0.0408 (19)0.0375 (18)0.0058 (14)0.0086 (15)0.0083 (14)
C250.0386 (17)0.0407 (19)0.0331 (18)0.0121 (15)0.0096 (15)0.0085 (14)
C260.0404 (19)0.047 (2)0.0393 (19)0.0120 (15)0.0087 (16)0.0082 (15)
C270.0357 (17)0.045 (2)0.0374 (18)0.0094 (14)0.0099 (15)0.0073 (15)
C280.073 (3)0.054 (2)0.064 (3)0.018 (2)0.028 (2)0.0161 (19)
C290.053 (2)0.046 (2)0.039 (2)0.0086 (17)0.0106 (17)0.0102 (16)
C300.049 (2)0.052 (2)0.048 (2)0.0097 (17)0.0065 (18)0.0083 (17)
C310.046 (2)0.046 (2)0.050 (2)0.0148 (16)0.0121 (17)0.0067 (16)
Cu10.0306 (2)0.0389 (2)0.0319 (2)0.00670 (16)0.00786 (17)0.00623 (16)
Cu20.0294 (2)0.0392 (2)0.0357 (2)0.00614 (16)0.00610 (17)0.00706 (17)
N10.0350 (15)0.056 (2)0.0389 (16)0.0030 (15)0.0138 (13)0.0124 (14)
N20.0294 (13)0.0387 (15)0.0337 (14)0.0065 (11)0.0047 (12)0.0060 (11)
N30.0333 (14)0.0336 (15)0.0357 (14)0.0082 (11)0.0055 (12)0.0080 (11)
N40.0363 (14)0.0335 (15)0.0369 (15)0.0047 (11)0.0089 (12)0.0077 (11)
N50.0377 (15)0.0382 (16)0.0396 (15)0.0064 (12)0.0085 (13)0.0101 (12)
N60.0390 (16)0.0447 (18)0.0441 (17)0.0095 (14)0.0097 (13)0.0116 (13)
N70.0527 (19)0.0490 (18)0.0412 (18)0.0131 (14)0.0059 (17)0.0157 (13)
O10.0314 (11)0.0410 (13)0.0313 (11)0.0037 (9)0.0112 (9)0.0085 (9)
O20.0411 (13)0.0646 (17)0.0581 (16)0.0069 (12)0.0175 (12)0.0152 (12)
O30.0499 (14)0.0556 (16)0.0528 (15)0.0184 (12)0.0165 (12)0.0113 (12)
O40.0368 (11)0.0434 (13)0.0353 (12)0.0079 (10)0.0057 (10)0.0047 (10)
O50.0363 (11)0.0360 (13)0.0454 (13)0.0038 (10)0.0134 (10)0.0061 (10)
O60.0293 (11)0.0421 (12)0.0372 (12)0.0073 (9)0.0062 (10)0.0017 (10)
O70.0360 (12)0.0408 (13)0.0446 (13)0.0108 (10)0.0076 (10)0.0067 (10)
O80.0343 (12)0.0401 (13)0.0456 (13)0.0076 (9)0.0055 (10)0.0092 (10)
O90.0277 (10)0.0387 (12)0.0375 (12)0.0047 (9)0.0038 (9)0.0065 (9)
O100.0416 (13)0.0560 (15)0.0557 (15)0.0037 (12)0.0152 (12)0.0170 (12)
O110.0517 (14)0.0473 (15)0.0501 (14)0.0166 (11)0.0135 (12)0.0091 (12)
O120.0371 (12)0.0471 (14)0.0319 (11)0.0077 (10)0.0077 (10)0.0071 (9)
O130.0411 (13)0.0475 (14)0.0440 (13)0.0099 (10)0.0079 (11)0.0084 (11)
O140.0463 (14)0.0674 (17)0.0476 (14)0.0090 (12)0.0095 (13)0.0089 (12)
O150.0554 (15)0.0668 (17)0.0512 (16)0.0173 (12)0.0122 (13)0.0104 (13)
O160.0432 (14)0.0529 (15)0.0508 (14)0.0095 (11)0.0143 (12)0.0097 (11)
Geometric parameters (Å, º) top
C1—C21.406 (4)C21—N51.265 (4)
C1—C61.393 (4)C22—C231.427 (4)
C1—O11.328 (3)C22—C271.409 (4)
C2—C31.415 (4)C23—C241.425 (4)
C2—C71.453 (4)C23—O91.307 (3)
C3—H30.9500C24—H240.9500
C3—C41.357 (4)C24—C251.377 (4)
C4—C51.387 (4)C25—H250.9500
C4—N11.473 (4)C25—C261.374 (4)
C5—H50.9500C26—C271.354 (4)
C5—C61.377 (4)C26—N61.472 (4)
C6—H60.9500C27—H270.9500
C7—H70.9500C28—H28A0.9800
C7—N21.291 (4)C28—H28B0.9800
C8—H8A0.9900C28—H28C0.9800
C8—H8B0.9900C28—C291.445 (5)
C8—C91.507 (4)C29—H29A0.9900
C8—O41.446 (3)C29—H29B0.9900
C9—H9A0.9900C29—O121.447 (4)
C9—H9B0.9900C30—H30A0.9800
C9—O51.421 (3)C30—H30B0.9800
C10—H100.9500C30—H30C0.9800
C10—C111.440 (4)C30—C311.515 (4)
C10—N31.303 (4)C31—H31A0.9900
C11—C121.393 (4)C31—H31B0.9900
C11—C161.379 (4)C31—O131.443 (4)
C12—C131.390 (4)Cu1—N21.945 (2)
C12—O61.345 (3)Cu1—N32.004 (2)
C13—C141.402 (4)Cu1—O1i2.3845 (19)
C13—C181.450 (4)Cu1—O11.9535 (18)
C14—H140.9500Cu1—O61.946 (2)
C14—C151.403 (4)Cu2—N42.043 (2)
C15—C161.381 (4)Cu2—N51.941 (2)
C15—C171.507 (4)Cu2—O61.9455 (19)
C16—H160.9500Cu2—O91.961 (2)
C17—H17A0.9800Cu2—O122.240 (2)
C17—H17B0.9800N1—O21.244 (3)
C17—H17C0.9800N1—O31.200 (3)
C18—H180.9500N2—O41.412 (3)
C18—N41.268 (3)N3—O51.402 (3)
C19—H19A0.9900N4—O71.412 (3)
C19—H19B0.9900N5—O81.414 (3)
C19—C201.493 (4)N6—O101.215 (3)
C19—O71.415 (3)N6—O111.222 (3)
C20—H20A0.9900N7—O141.244 (3)
C20—H20B0.9900N7—O151.249 (3)
C20—O81.429 (4)N7—O161.257 (3)
C21—H210.9500O12—H12B0.9900
C21—C221.428 (4)O13—H130.8400
C6—C1—C2118.8 (3)C26—C25—C24120.2 (3)
O1—C1—C2121.8 (3)C26—C25—H25119.9
O1—C1—C6119.4 (3)C25—C26—N6120.4 (3)
C1—C2—C3120.4 (3)C27—C26—C25121.4 (3)
C1—C2—C7122.6 (3)C27—C26—N6118.1 (3)
C3—C2—C7116.9 (3)C22—C27—H27119.7
C2—C3—H3121.2C26—C27—C22120.5 (3)
C4—C3—C2117.5 (3)C26—C27—H27119.7
C4—C3—H3121.2H28A—C28—H28B109.5
C3—C4—C5123.7 (3)H28A—C28—H28C109.5
C3—C4—N1117.1 (3)H28B—C28—H28C109.5
C5—C4—N1119.1 (3)C29—C28—H28A109.5
C4—C5—H5120.9C29—C28—H28B109.5
C6—C5—C4118.3 (3)C29—C28—H28C109.5
C6—C5—H5120.9C28—C29—H29A109.5
C1—C6—H6119.4C28—C29—H29B109.5
C5—C6—C1121.1 (3)C28—C29—O12110.8 (3)
C5—C6—H6119.4H29A—C29—H29B108.1
C2—C7—H7118.3O12—C29—H29A109.5
N2—C7—C2123.4 (3)O12—C29—H29B109.5
N2—C7—H7118.3H30A—C30—H30B109.5
H8A—C8—H8B107.9H30A—C30—H30C109.5
C9—C8—H8A109.3H30B—C30—H30C109.5
C9—C8—H8B109.3C31—C30—H30A109.5
O4—C8—H8A109.3C31—C30—H30B109.5
O4—C8—H8B109.3C31—C30—H30C109.5
O4—C8—C9111.7 (2)C30—C31—H31A110.1
C8—C9—H9A109.7C30—C31—H31B110.1
C8—C9—H9B109.7H31A—C31—H31B108.4
H9A—C9—H9B108.2O13—C31—C30108.1 (3)
O5—C9—C8110.0 (2)O13—C31—H31A110.1
O5—C9—H9A109.7O13—C31—H31B110.1
O5—C9—H9B109.7N2—Cu1—N398.58 (10)
C11—C10—H10117.5N2—Cu1—O1i93.27 (8)
N3—C10—H10117.5N2—Cu1—O188.29 (9)
N3—C10—C11124.9 (3)N2—Cu1—O6166.15 (9)
C12—C11—C10122.7 (3)N3—Cu1—O1i95.75 (8)
C16—C11—C10116.8 (3)O1—Cu1—N3172.59 (9)
C16—C11—C12120.5 (3)O1—Cu1—O1i81.00 (8)
C13—C12—C11118.7 (3)O6—Cu1—N386.54 (9)
O6—C12—C11121.1 (3)O6—Cu1—O187.40 (8)
O6—C12—C13120.2 (3)O6—Cu1—O1i99.04 (8)
C12—C13—C14119.9 (3)N4—Cu2—O1291.33 (9)
C12—C13—C18123.1 (3)N5—Cu2—N497.49 (10)
C14—C13—C18116.8 (3)N5—Cu2—O6171.65 (9)
C13—C14—H14119.3N5—Cu2—O989.83 (9)
C13—C14—C15121.4 (3)N5—Cu2—O1295.28 (9)
C15—C14—H14119.3O6—Cu2—N485.57 (9)
C14—C15—C17120.1 (3)O6—Cu2—O985.97 (8)
C16—C15—C14116.9 (3)O6—Cu2—O1292.41 (8)
C16—C15—C17122.9 (3)O9—Cu2—N4168.30 (9)
C11—C16—H16118.8O9—Cu2—O1297.09 (8)
C15—C16—C11122.4 (3)O2—N1—C4116.8 (3)
C15—C16—H16118.8O3—N1—C4119.8 (3)
C15—C17—H17A109.5O3—N1—O2123.4 (3)
C15—C17—H17B109.5C7—N2—Cu1126.3 (2)
C15—C17—H17C109.5C7—N2—O4112.5 (2)
H17A—C17—H17B109.5O4—N2—Cu1121.11 (17)
H17A—C17—H17C109.5C10—N3—Cu1124.5 (2)
H17B—C17—H17C109.5C10—N3—O5109.3 (2)
C13—C18—H18117.6O5—N3—Cu1124.53 (17)
N4—C18—C13124.9 (3)C18—N4—Cu2123.3 (2)
N4—C18—H18117.6C18—N4—O7109.0 (2)
H19A—C19—H19B108.1O7—N4—Cu2127.09 (17)
C20—C19—H19A109.5C21—N5—Cu2129.2 (2)
C20—C19—H19B109.5C21—N5—O8113.1 (2)
O7—C19—H19A109.5O8—N5—Cu2117.21 (17)
O7—C19—H19B109.5O10—N6—C26118.5 (3)
O7—C19—C20110.5 (2)O10—N6—O11123.8 (3)
C19—C20—H20A109.0O11—N6—C26117.7 (3)
C19—C20—H20B109.0O14—N7—O15118.8 (3)
H20A—C20—H20B107.8O14—N7—O16121.1 (3)
O8—C20—C19112.7 (2)O15—N7—O16120.0 (3)
O8—C20—H20A109.0C1—O1—Cu1i117.54 (16)
O8—C20—H20B109.0C1—O1—Cu1124.26 (18)
C22—C21—H21117.7Cu1—O1—Cu1i99.00 (8)
N5—C21—H21117.7N2—O4—C8111.2 (2)
N5—C21—C22124.6 (3)N3—O5—C9110.2 (2)
C23—C22—C21123.0 (3)C12—O6—Cu1125.76 (17)
C27—C22—C21117.7 (3)C12—O6—Cu2122.92 (17)
C27—C22—C23119.2 (3)Cu1—O6—Cu2111.07 (9)
C24—C23—C22117.5 (3)N4—O7—C19112.7 (2)
O9—C23—C22122.8 (3)N5—O8—C20110.7 (2)
O9—C23—C24119.8 (3)C23—O9—Cu2128.45 (19)
C23—C24—H24119.7C29—O12—Cu2117.40 (17)
C25—C24—C23120.6 (3)C29—O12—H12B107.7
C25—C24—H24119.7Cu2—O12—H12B107.9
C24—C25—H25119.9C31—O13—H13109.5
Symmetry code: (i) x+1, y+1, z+2.
(3) top
Crystal data top
C29H30Br2Cu2N6O12·CHCl3F(000) = 2112
Mr = 1060.86Dx = 1.796 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 14.3330 (4) ÅCell parameters from 9688 reflections
b = 17.1049 (4) Åθ = 2.4–26.7°
c = 16.3502 (5) ŵ = 3.39 mm1
β = 101.859 (2)°T = 173 K
V = 3922.93 (19) Å3Block
Z = 40.26 × 0.24 × 0.23 mm
Data collection top
Bruker D8 Venture
diffractometer
7711 reflections with I > 2σ(I)
φ and ω scansRint = 0.048
Absorption correction: multi-scan
SADABS
θmax = 26.8°, θmin = 2.4°
Tmin = 0.607, Tmax = 0.745h = 1818
35876 measured reflectionsk = 2121
8303 independent reflectionsl = 2020
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH 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 = 1.06Δρmax = 0.55 e Å3
8303 reflectionsΔρmin = 0.56 e Å3
540 parametersAbsolute structure: Refined as an inversion twin.
119 restraintsAbsolute 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
xyzUiso*/UeqOcc. (<1)
Br10.51014 (3)0.58335 (3)0.61276 (3)0.03264 (11)
Br20.19557 (4)0.61898 (3)0.46705 (3)0.03903 (13)
C10.2776 (3)0.5489 (2)0.6849 (3)0.0211 (8)
C20.2944 (3)0.6299 (3)0.6963 (3)0.0265 (9)
H20.3241820.6579310.6585180.032*
C30.2678 (3)0.6688 (3)0.7620 (3)0.0295 (9)
H30.2795610.7232270.7694750.035*
C40.2238 (3)0.6279 (3)0.8172 (3)0.0285 (9)
C50.2077 (3)0.5493 (3)0.8094 (3)0.0263 (9)
H50.1785530.5224180.8484770.032*
C60.2344 (3)0.5082 (3)0.7432 (3)0.0241 (8)
C70.2082 (3)0.4266 (3)0.7363 (3)0.0259 (9)
H70.1738340.4067370.7757130.031*
C80.1670 (4)0.2608 (3)0.6147 (3)0.0351 (10)
H8A0.1667240.2959390.5664770.042*
H8B0.1035440.2357860.6072990.042*
C90.2414 (5)0.2001 (3)0.6178 (4)0.0437 (13)
H9A0.2342100.1604370.6601450.052*
H9B0.2320490.1736290.5628850.052*
C100.3989 (4)0.2706 (3)0.5298 (3)0.0294 (10)
H100.4161650.2169750.5306810.035*
C110.4321 (3)0.3206 (2)0.4706 (3)0.0257 (9)
C120.4114 (3)0.4013 (2)0.4620 (3)0.0209 (8)
C130.4465 (3)0.4427 (3)0.3995 (3)0.0225 (8)
C140.4989 (3)0.4030 (3)0.3492 (3)0.0293 (10)
H140.5208640.4314380.3069020.035*
C150.5204 (4)0.3233 (3)0.3581 (3)0.0329 (10)
C160.4870 (3)0.2839 (3)0.4193 (3)0.0317 (10)
H160.5012820.2298380.4273210.038*
C170.5778 (5)0.2837 (4)0.3036 (4)0.0501 (15)
H17A0.5422900.2842220.2456300.075*
H17B0.5902920.2295000.3221520.075*
H17C0.6384020.3113300.3074080.075*
C180.4301 (3)0.5248 (3)0.3803 (3)0.0246 (9)
H180.4471200.5429080.3304470.030*
C190.4090 (5)0.7128 (3)0.4357 (3)0.0423 (13)
H19A0.4783620.7117900.4594890.051*
H19B0.3744690.7100390.4821390.051*
C200.3831 (4)0.7857 (3)0.3864 (3)0.0400 (12)
H20A0.3181350.7809750.3515610.048*
H20B0.3841170.8308370.4244730.048*
C210.4823 (4)0.8735 (3)0.2372 (3)0.0354 (11)
H210.5178680.8291350.2265000.042*
C220.4829 (4)0.9450 (3)0.1864 (3)0.0350 (11)
C230.5251 (4)0.9412 (3)0.1161 (4)0.0369 (11)
C240.5307 (4)1.0068 (3)0.0679 (4)0.0447 (13)
H240.5614941.0038040.0218010.054*
C250.4915 (4)1.0767 (3)0.0866 (4)0.0452 (13)
H250.4947751.1220390.0536670.054*
C260.4479 (4)1.0792 (3)0.1536 (4)0.0476 (14)
C270.4433 (4)1.0149 (3)0.2061 (4)0.0432 (12)
H270.4142911.0191020.2531360.052*
C280.6058 (7)0.3466 (8)0.6739 (7)0.106 (4)
H28A0.5738770.3233870.6207190.159*
H28B0.6559630.3111820.7022740.159*
H28C0.6342460.3967300.6633850.159*
C290.5371 (5)0.3590 (4)0.7262 (5)0.0617 (17)
H29A0.5719340.3757400.7821630.074*
H29B0.5062920.3083350.7331740.074*
Cu10.31508 (4)0.39953 (3)0.60575 (3)0.02174 (11)
Cu20.34921 (3)0.55862 (3)0.52622 (3)0.02157 (12)
N10.1933 (3)0.6696 (3)0.8857 (3)0.0370 (10)
N20.2271 (3)0.3789 (2)0.6818 (2)0.0254 (8)
N30.3480 (3)0.2930 (2)0.5814 (2)0.0290 (8)
N40.3954 (3)0.5754 (2)0.4226 (2)0.0237 (7)
N50.4353 (3)0.8702 (2)0.2947 (3)0.0360 (9)
N60.4047 (5)1.1524 (3)0.1733 (4)0.0648 (16)
O10.2997 (2)0.51216 (17)0.62030 (18)0.0234 (6)
O20.2051 (3)0.7402 (2)0.8909 (3)0.0527 (11)
O30.1578 (3)0.6307 (2)0.9351 (2)0.0466 (9)
O40.1857 (3)0.30552 (19)0.6911 (2)0.0371 (8)
O50.3381 (3)0.23237 (19)0.6384 (2)0.0387 (8)
O60.3608 (2)0.43761 (16)0.50914 (18)0.0217 (6)
O70.3831 (2)0.64799 (17)0.38000 (19)0.0294 (7)
O80.4513 (3)0.7971 (2)0.3342 (2)0.0400 (8)
O90.5600 (3)0.8715 (2)0.0983 (3)0.0432 (9)
H90.6012640.8784560.0692210.065*
O100.3725 (5)1.1552 (3)0.2370 (5)0.0880 (19)
O110.4049 (5)1.2086 (3)0.1261 (4)0.0887 (19)
O120.4629 (3)0.4161 (2)0.6960 (2)0.0373 (8)
H120.4972 (19)0.4563 (19)0.681 (3)0.056*
C300.7369 (11)0.4317 (14)0.8697 (15)0.100 (7)0.492 (7)
H300.7253210.3843820.8331610.120*0.492 (7)
C30A0.7911 (14)0.5079 (9)0.8951 (12)0.087 (5)0.508 (7)
H30A0.8525970.5361300.8973410.104*0.508 (7)
Cl0A0.8598 (5)0.4390 (7)0.9319 (6)0.140 (3)0.492 (7)
Cl10.7239 (12)0.5184 (11)0.8160 (12)0.207 (5)0.492 (7)
Cl1A0.7173 (3)0.5183 (3)0.7967 (3)0.0605 (11)0.508 (7)
Cl20.6614 (4)0.4379 (4)0.9445 (4)0.115 (2)0.492 (7)
Cl2A0.7357 (5)0.5416 (6)0.9723 (5)0.149 (3)0.508 (7)
Cl30.8109 (9)0.4065 (4)0.9040 (6)0.139 (3)0.508 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0400 (2)0.0315 (2)0.0275 (2)0.0132 (2)0.00937 (18)0.00038 (18)
Br20.0448 (3)0.0460 (3)0.0307 (2)0.0171 (2)0.0180 (2)0.0093 (2)
C10.0231 (19)0.025 (2)0.0170 (19)0.0012 (16)0.0078 (15)0.0019 (16)
C20.035 (2)0.023 (2)0.024 (2)0.0019 (17)0.0113 (17)0.0014 (16)
C30.036 (2)0.022 (2)0.030 (2)0.0010 (18)0.0085 (18)0.0070 (17)
C40.029 (2)0.036 (2)0.021 (2)0.0055 (19)0.0078 (17)0.0076 (18)
C50.029 (2)0.036 (2)0.018 (2)0.0010 (18)0.0121 (16)0.0009 (17)
C60.029 (2)0.026 (2)0.0196 (19)0.0000 (17)0.0088 (16)0.0004 (16)
C70.032 (2)0.031 (2)0.018 (2)0.0031 (18)0.0125 (17)0.0061 (16)
C80.051 (3)0.028 (2)0.031 (2)0.018 (2)0.020 (2)0.0027 (18)
C90.075 (4)0.021 (2)0.044 (3)0.013 (2)0.033 (3)0.000 (2)
C100.047 (3)0.019 (2)0.025 (2)0.0086 (19)0.0136 (19)0.0021 (16)
C110.037 (2)0.0214 (19)0.020 (2)0.0062 (17)0.0098 (17)0.0007 (16)
C120.024 (2)0.022 (2)0.0174 (19)0.0006 (16)0.0057 (16)0.0027 (15)
C130.0250 (19)0.028 (2)0.0162 (19)0.0001 (16)0.0086 (15)0.0026 (15)
C140.035 (2)0.035 (2)0.021 (2)0.0061 (19)0.0149 (19)0.0024 (18)
C150.042 (3)0.035 (2)0.026 (2)0.016 (2)0.0160 (19)0.0017 (19)
C160.041 (3)0.029 (2)0.027 (2)0.016 (2)0.0119 (19)0.0014 (18)
C170.067 (4)0.054 (3)0.038 (3)0.031 (3)0.031 (3)0.009 (3)
C180.031 (2)0.028 (2)0.018 (2)0.0017 (17)0.0110 (17)0.0015 (16)
C190.080 (4)0.022 (2)0.028 (2)0.011 (2)0.020 (2)0.0001 (19)
C200.065 (4)0.022 (2)0.041 (3)0.002 (2)0.029 (3)0.0022 (19)
C210.036 (3)0.029 (2)0.044 (3)0.001 (2)0.014 (2)0.000 (2)
C220.035 (2)0.029 (2)0.043 (3)0.006 (2)0.013 (2)0.004 (2)
C230.033 (2)0.036 (2)0.042 (3)0.002 (2)0.009 (2)0.003 (2)
C240.045 (3)0.047 (3)0.044 (3)0.007 (2)0.017 (2)0.012 (2)
C250.051 (3)0.032 (3)0.052 (3)0.003 (2)0.007 (3)0.015 (2)
C260.050 (3)0.030 (3)0.063 (4)0.000 (2)0.013 (3)0.008 (2)
C270.047 (3)0.036 (3)0.050 (3)0.001 (2)0.019 (3)0.006 (2)
C280.073 (6)0.145 (10)0.100 (7)0.019 (6)0.018 (5)0.027 (7)
C290.067 (4)0.047 (3)0.068 (5)0.007 (3)0.008 (3)0.003 (3)
Cu10.0332 (3)0.0155 (2)0.0206 (2)0.0021 (2)0.0150 (2)0.00117 (19)
Cu20.0332 (3)0.0172 (2)0.0180 (2)0.0013 (2)0.01399 (19)0.00117 (19)
N10.039 (2)0.044 (3)0.029 (2)0.0091 (19)0.0110 (17)0.0119 (18)
N20.038 (2)0.0190 (17)0.0236 (18)0.0072 (15)0.0156 (15)0.0024 (14)
N30.044 (2)0.0194 (17)0.0266 (19)0.0019 (16)0.0149 (16)0.0079 (14)
N40.0357 (19)0.0175 (16)0.0209 (18)0.0006 (14)0.0129 (15)0.0042 (13)
N50.046 (2)0.0224 (18)0.041 (2)0.0027 (17)0.0115 (19)0.0050 (16)
N60.080 (4)0.030 (2)0.089 (5)0.008 (3)0.030 (4)0.008 (3)
O10.0337 (16)0.0200 (14)0.0202 (14)0.0023 (12)0.0144 (12)0.0003 (11)
O20.070 (3)0.040 (2)0.053 (2)0.008 (2)0.026 (2)0.0211 (19)
O30.056 (2)0.059 (2)0.0305 (19)0.0118 (19)0.0217 (17)0.0060 (17)
O40.064 (2)0.0249 (16)0.0310 (18)0.0197 (16)0.0291 (16)0.0034 (13)
O50.058 (2)0.0237 (16)0.0396 (19)0.0035 (15)0.0225 (17)0.0181 (14)
O60.0315 (15)0.0167 (13)0.0206 (15)0.0011 (12)0.0140 (12)0.0001 (11)
O70.053 (2)0.0182 (14)0.0205 (15)0.0011 (13)0.0167 (14)0.0050 (11)
O80.051 (2)0.0258 (17)0.048 (2)0.0005 (15)0.0194 (17)0.0135 (15)
O90.051 (2)0.0347 (19)0.052 (2)0.0019 (16)0.0289 (19)0.0009 (16)
O100.120 (5)0.043 (3)0.115 (5)0.025 (3)0.056 (4)0.004 (3)
O110.124 (5)0.035 (2)0.109 (5)0.016 (3)0.027 (4)0.025 (3)
O120.044 (2)0.0334 (18)0.0342 (19)0.0009 (15)0.0078 (16)0.0008 (15)
C300.074 (11)0.118 (17)0.104 (16)0.044 (12)0.006 (11)0.043 (14)
C30A0.090 (12)0.069 (10)0.092 (13)0.006 (9)0.002 (10)0.008 (9)
Cl0A0.078 (3)0.174 (7)0.148 (6)0.002 (4)0.024 (4)0.021 (6)
Cl10.183 (9)0.228 (10)0.204 (10)0.036 (8)0.026 (8)0.041 (9)
Cl1A0.0417 (17)0.081 (3)0.060 (2)0.0033 (17)0.0151 (15)0.0030 (17)
Cl20.099 (4)0.135 (5)0.121 (5)0.052 (3)0.042 (3)0.057 (4)
Cl2A0.101 (4)0.226 (8)0.115 (5)0.019 (5)0.011 (4)0.035 (5)
Cl30.193 (8)0.089 (4)0.127 (6)0.003 (5)0.017 (6)0.024 (4)
Geometric parameters (Å, º) top
Br1—Cu22.4819 (7)C20—O81.437 (6)
Br2—Cu22.4445 (7)C21—H210.9500
C1—C21.412 (6)C21—C221.480 (7)
C1—C61.422 (6)C21—N51.264 (7)
C1—O11.322 (5)C22—C231.405 (8)
C2—H20.9500C22—C271.390 (8)
C2—C31.382 (6)C23—C241.384 (7)
C3—H30.9500C23—O91.348 (6)
C3—C41.390 (7)C24—H240.9500
C4—C51.367 (7)C24—C251.381 (8)
C4—N11.469 (5)C25—H250.9500
C5—H50.9500C25—C261.370 (9)
C5—C61.408 (6)C26—C271.404 (8)
C6—C71.443 (6)C26—N61.461 (8)
C7—H70.9500C27—H270.9500
C7—N21.279 (6)C28—H28A0.9800
C8—H8A0.9900C28—H28B0.9800
C8—H8B0.9900C28—H28C0.9800
C8—C91.482 (8)C28—C291.446 (12)
C8—O41.442 (6)C29—H29A0.9900
C9—H9A0.9900C29—H29B0.9900
C9—H9B0.9900C29—O121.454 (8)
C9—O51.465 (7)Cu1—N21.976 (4)
C10—H100.9500Cu1—N31.943 (4)
C10—C111.443 (6)Cu1—O11.959 (3)
C10—N31.282 (6)Cu1—O61.943 (3)
C11—C121.413 (6)Cu1—O122.337 (4)
C11—C161.410 (6)Cu2—N41.962 (4)
C12—C131.418 (6)Cu2—O11.987 (3)
C12—O61.317 (5)Cu2—O62.100 (3)
C13—C141.400 (6)N1—O21.220 (6)
C13—C181.447 (6)N1—O31.233 (6)
C14—H140.9500N2—O41.410 (4)
C14—C151.398 (7)N3—O51.421 (4)
C15—C161.371 (7)N4—O71.417 (4)
C15—C171.494 (6)N5—O81.404 (5)
C16—H160.9500N6—O101.225 (8)
C17—H17A0.9800N6—O111.233 (7)
C17—H17B0.9800O9—H90.8400
C17—H17C0.9800O12—H120.906 (14)
C18—H180.9500C30—H301.0000
C18—N41.272 (6)C30—Cl0A1.848 (19)
C19—H19A0.9900C30—Cl11.71 (3)
C19—H19B0.9900C30—Cl21.79 (2)
C19—C201.490 (7)C30A—H30A1.0000
C19—O71.433 (6)C30A—Cl1A1.74 (2)
C20—H20A0.9900C30A—Cl2A1.722 (18)
C20—H20B0.9900C30A—Cl31.758 (16)
C2—C1—C6118.5 (4)C25—C24—C23120.2 (5)
O1—C1—C2120.7 (4)C25—C24—H24119.9
O1—C1—C6120.8 (4)C24—C25—H25120.8
C1—C2—H2119.7C26—C25—C24118.5 (5)
C3—C2—C1120.6 (4)C26—C25—H25120.8
C3—C2—H2119.7C25—C26—C27123.4 (5)
C2—C3—H3120.1C25—C26—N6119.1 (5)
C2—C3—C4119.8 (4)C27—C26—N6117.5 (6)
C4—C3—H3120.1C22—C27—C26117.4 (5)
C3—C4—N1119.8 (4)C22—C27—H27121.3
C5—C4—C3121.7 (4)C26—C27—H27121.3
C5—C4—N1118.5 (4)H28A—C28—H28B109.5
C4—C5—H5120.2H28A—C28—H28C109.5
C4—C5—C6119.6 (4)H28B—C28—H28C109.5
C6—C5—H5120.2C29—C28—H28A109.5
C1—C6—C7124.3 (4)C29—C28—H28B109.5
C5—C6—C1119.8 (4)C29—C28—H28C109.5
C5—C6—C7115.7 (4)C28—C29—H29A108.3
C6—C7—H7117.2C28—C29—H29B108.3
N2—C7—C6125.6 (4)C28—C29—O12116.0 (7)
N2—C7—H7117.2H29A—C29—H29B107.4
H8A—C8—H8B108.2O12—C29—H29A108.3
C9—C8—H8A109.7O12—C29—H29B108.3
C9—C8—H8B109.7N2—Cu1—O12103.70 (15)
O4—C8—H8A109.7N3—Cu1—N2100.05 (15)
O4—C8—H8B109.7N3—Cu1—O1169.97 (14)
O4—C8—C9109.7 (5)N3—Cu1—O1290.91 (16)
C8—C9—H9A109.1O1—Cu1—N289.85 (13)
C8—C9—H9B109.1O1—Cu1—O1285.06 (13)
H9A—C9—H9B107.8O6—Cu1—N2159.56 (14)
O5—C9—C8112.6 (4)O6—Cu1—N390.64 (14)
O5—C9—H9A109.1O6—Cu1—O180.45 (11)
O5—C9—H9B109.1O6—Cu1—O1293.41 (13)
C11—C10—H10117.4Br2—Cu2—Br1144.07 (3)
N3—C10—H10117.4N4—Cu2—Br191.63 (11)
N3—C10—C11125.1 (4)N4—Cu2—Br291.86 (11)
C12—C11—C10123.6 (4)N4—Cu2—O1164.60 (13)
C16—C11—C10115.9 (4)N4—Cu2—O688.83 (13)
C16—C11—C12120.5 (4)O1—Cu2—Br193.70 (9)
C11—C12—C13117.5 (4)O1—Cu2—Br292.27 (9)
O6—C12—C11122.2 (4)O1—Cu2—O676.08 (11)
O6—C12—C13120.3 (4)O6—Cu2—Br198.87 (9)
C12—C13—C18125.1 (4)O6—Cu2—Br2116.95 (9)
C14—C13—C12119.6 (4)O2—N1—C4118.3 (4)
C14—C13—C18115.3 (4)O2—N1—O3124.0 (4)
C13—C14—H14118.5O3—N1—C4117.8 (4)
C15—C14—C13123.0 (4)C7—N2—Cu1125.4 (3)
C15—C14—H14118.5C7—N2—O4109.8 (3)
C14—C15—C17121.1 (4)O4—N2—Cu1124.3 (3)
C16—C15—C14117.0 (4)C10—N3—Cu1127.6 (3)
C16—C15—C17122.0 (4)C10—N3—O5111.1 (3)
C11—C16—H16118.8O5—N3—Cu1119.3 (3)
C15—C16—C11122.4 (4)C18—N4—Cu2127.5 (3)
C15—C16—H16118.8C18—N4—O7110.6 (3)
C15—C17—H17A109.5O7—N4—Cu2121.6 (3)
C15—C17—H17B109.5C21—N5—O8108.7 (4)
C15—C17—H17C109.5O10—N6—C26118.2 (5)
H17A—C17—H17B109.5O10—N6—O11123.4 (6)
H17A—C17—H17C109.5O11—N6—C26118.4 (6)
H17B—C17—H17C109.5C1—O1—Cu1128.0 (3)
C13—C18—H18116.3C1—O1—Cu2127.6 (3)
N4—C18—C13127.4 (4)Cu1—O1—Cu2103.44 (13)
N4—C18—H18116.3N2—O4—C8112.7 (3)
H19A—C19—H19B108.5N3—O5—C9110.0 (4)
C20—C19—H19A110.2C12—O6—Cu1129.5 (3)
C20—C19—H19B110.2C12—O6—Cu2127.7 (2)
O7—C19—H19A110.2Cu1—O6—Cu299.97 (12)
O7—C19—H19B110.2N4—O7—C19112.0 (3)
O7—C19—C20107.5 (4)N5—O8—C20109.1 (4)
C19—C20—H20A110.1C23—O9—H9109.5
C19—C20—H20B110.1C29—O12—Cu1129.7 (4)
H20A—C20—H20B108.4C29—O12—H12102 (2)
O8—C20—C19108.1 (4)Cu1—O12—H12113 (2)
O8—C20—H20A110.1Cl0A—C30—H30114.0
O8—C20—H20B110.1Cl1—C30—H30114.0
C22—C21—H21119.3Cl1—C30—Cl0A102.4 (13)
N5—C21—H21119.3Cl1—C30—Cl2106.3 (13)
N5—C21—C22121.3 (5)Cl2—C30—H30114.0
C23—C22—C21118.3 (5)Cl2—C30—Cl0A105.1 (13)
C27—C22—C21122.1 (5)Cl1A—C30A—H30A110.3
C27—C22—C23119.6 (5)Cl1A—C30A—Cl3103.5 (9)
C24—C23—C22120.9 (5)Cl2A—C30A—H30A110.3
O9—C23—C22117.3 (5)Cl2A—C30A—Cl1A111.0 (10)
O9—C23—C24121.8 (5)Cl2A—C30A—Cl3111.2 (13)
C23—C24—H24119.9Cl3—C30A—H30A110.3
 

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