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A new chiral catalyst for the enantioselective Diels–Alder reaction has been synthesized, namely [(4S,4′S)-4,4′,5,5′-tetra­hydro-4,4′-diiso­propyl-2,2′-(di­benzyl­methyl­ene)­dioxazole-κ2N,N′]­bis(tri­fluoro­methanesulfonato-κO)copper(II) tetra­hy­dro­furan solvate, [Cu(CF3O3S)2(C27H34N2O2)]·C4H8O. It is used in a model study for comparing solid-phase and solution-phase catalyst activity.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009303/ac6005sup1.cif
Contains datablocks global, 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009303/ac60054sup2.hkl
Contains datablock 4

CCDC reference: 189307

Key indicators

  • Single-crystal X-ray study
  • T = 91 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.027
  • wR factor = 0.064
  • Data-to-parameter ratio = 24.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 31.50 From the CIF: _reflns_number_total 11771 Count of symmetry unique reflns 6810 Completeness (_total/calc) 172.85% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4961 Fraction of Friedel pairs measured 0.728 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97.

[(4S,4'S)-4,4',5,5'-Tetrahydro-4,4'-diisopropyl-2,2'- (dibenzylmethylene)dioxazole-κ2N,N']bis(trifluoromethanesulfonato- kO)copper(II) tetrahydrofuran solvate top
Crystal data top
[Cu(CF3O3S)2(C27H34N2O2)]·C4H8ODx = 1.522 Mg m3
Mr = 852.35Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 973 reflections
a = 10.5996 (14) Åθ = 2.2–30.0°
b = 17.933 (2) ŵ = 0.78 mm1
c = 19.575 (3) ÅT = 91 K
V = 3720.7 (8) Å3Plate, green
Z = 40.43 × 0.17 × 0.09 mm
F(000) = 1764
Data collection top
Bruker SMART 1000
diffractometer
11771 independent reflections
Radiation source: normal-focus sealed tube10510 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 8.3 pixels mm-1θmax = 31.5°, θmin = 2.1°
ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
k = 2525
Tmin = 0.729, Tmax = 0.932l = 2827
50497 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.064 w = 1/[σ2(Fo2) + (0.032P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.003
11771 reflectionsΔρmax = 0.33 e Å3
482 parametersΔρmin = 0.26 e Å3
0 restraintsAbsolute structure: Flack (1983), 0000 Friedel reflections
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.000 (5)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.854914 (16)0.833187 (9)0.212901 (9)0.01497 (4)
S10.93307 (4)0.75223 (2)0.33046 (2)0.02292 (8)
S20.98609 (3)0.73964 (2)0.092744 (19)0.01842 (7)
F10.83270 (13)0.85891 (7)0.40413 (6)0.0454 (3)
F21.00934 (14)0.81915 (8)0.44212 (7)0.0602 (4)
F30.84239 (16)0.75288 (7)0.45427 (6)0.0611 (4)
F41.18682 (9)0.82274 (5)0.11382 (6)0.0323 (2)
F51.20362 (10)0.71183 (6)0.15220 (6)0.0362 (3)
F61.21410 (10)0.73199 (7)0.04414 (6)0.0411 (3)
O10.49764 (10)0.86349 (6)0.13682 (6)0.0202 (2)
O20.71960 (11)1.03582 (6)0.27600 (7)0.0288 (3)
O30.98163 (10)0.81408 (5)0.28784 (6)0.0212 (2)
O40.81038 (11)0.72923 (7)0.30791 (6)0.0277 (3)
O51.02406 (13)0.69641 (7)0.34555 (8)0.0402 (3)
O60.94007 (10)0.75323 (6)0.16258 (5)0.0203 (2)
O70.97486 (11)0.66284 (7)0.07358 (6)0.0299 (3)
O80.94825 (11)0.79518 (7)0.04462 (6)0.0291 (3)
N10.69081 (11)0.82858 (6)0.16839 (6)0.0153 (2)
N20.82320 (11)0.93289 (6)0.24650 (6)0.0174 (2)
C10.64452 (14)0.76432 (7)0.12695 (7)0.0165 (2)
H10.69900.75910.08550.020*
C20.51287 (15)0.79086 (8)0.10469 (9)0.0231 (3)
H2A0.50780.79510.05430.028*
H2B0.44700.75580.12050.028*
C30.60443 (13)0.87801 (8)0.17029 (8)0.0166 (3)
C40.60324 (14)0.95422 (8)0.20295 (8)0.0199 (3)
C50.72112 (14)0.97013 (8)0.24304 (8)0.0203 (3)
C60.83785 (16)1.03886 (10)0.31526 (10)0.0331 (4)
H6A0.82271.02740.36400.040*
H6B0.87751.08870.31160.040*
C70.92030 (14)0.97926 (8)0.28200 (8)0.0196 (3)
H70.96440.94920.31780.024*
C80.64520 (14)0.69021 (7)0.16616 (7)0.0173 (2)
H80.73320.68170.18290.021*
C90.61360 (17)0.62757 (8)0.11636 (9)0.0270 (4)
H9A0.61880.57950.14000.040*
H9B0.67380.62830.07830.040*
H9C0.52790.63470.09870.040*
C100.55838 (15)0.68985 (9)0.22830 (8)0.0239 (3)
H10A0.57220.73530.25510.036*
H10B0.57680.64610.25660.036*
H10C0.47030.68800.21310.036*
C111.01588 (15)1.01139 (8)0.23135 (8)0.0213 (3)
H110.97381.05200.20480.026*
C121.12617 (16)1.04531 (9)0.27125 (9)0.0280 (4)
H12A1.09361.08040.30530.042*
H12B1.18231.07170.23970.042*
H12C1.17321.00550.29430.042*
C131.06329 (16)0.95254 (9)0.18103 (9)0.0249 (3)
H13A1.09320.90880.20630.037*
H13B1.13270.97330.15400.037*
H13C0.99430.93780.15060.037*
C140.59315 (15)1.01419 (8)0.14458 (9)0.0233 (3)
H14A0.51261.00650.12000.028*
H14B0.58981.06420.16590.028*
C150.69870 (15)1.01336 (8)0.09345 (9)0.0218 (3)
C160.79508 (16)1.06637 (9)0.09590 (9)0.0247 (3)
H160.79251.10430.12980.030*
C170.89372 (17)1.06473 (9)0.05023 (9)0.0288 (4)
H170.95751.10190.05240.035*
C180.90068 (17)1.00904 (10)0.00077 (9)0.0282 (3)
H180.97001.00720.03000.034*
C190.80441 (18)0.95599 (9)0.00303 (9)0.0274 (3)
H190.80760.91790.03680.033*
C200.70477 (17)0.95884 (9)0.04213 (8)0.0255 (3)
H200.63890.92320.03840.031*
C210.48320 (15)0.96113 (9)0.24858 (9)0.0250 (3)
H21A0.49161.00630.27720.030*
H21B0.40910.96840.21850.030*
C220.45762 (14)0.89515 (9)0.29488 (9)0.0241 (3)
C230.53722 (16)0.87752 (11)0.34926 (9)0.0299 (4)
H230.60890.90780.35810.036*
C240.51289 (19)0.81638 (11)0.39051 (9)0.0352 (4)
H240.56870.80450.42690.042*
C250.40649 (19)0.77221 (11)0.37870 (9)0.0337 (4)
H250.38950.73040.40700.040*
C260.32603 (16)0.78981 (10)0.32546 (10)0.0320 (4)
H260.25300.76040.31740.038*
C270.35240 (15)0.85054 (9)0.28390 (9)0.0284 (3)
H270.29720.86190.24710.034*
C280.9030 (2)0.79827 (11)0.41210 (9)0.0354 (4)
C291.15691 (14)0.75273 (8)0.10168 (8)0.0207 (3)
O100.31077 (11)1.01305 (6)0.08637 (6)0.0257 (2)
C300.2864 (2)1.08983 (10)0.07124 (11)0.0411 (5)
H30A0.36231.12030.08050.049*
H30B0.21631.10860.09990.049*
C310.25159 (17)1.09448 (11)0.00328 (10)0.0365 (4)
H31A0.28451.14070.02440.044*
H31B0.15911.09220.00980.044*
C320.3162 (2)1.02563 (11)0.03220 (10)0.0438 (5)
H32A0.27511.00850.07480.053*
H32B0.40681.03490.04110.053*
C330.2978 (2)0.97045 (10)0.02505 (9)0.0355 (4)
H33A0.21310.94730.02250.043*
H33B0.36240.93060.02300.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01326 (7)0.01309 (7)0.01857 (8)0.00066 (6)0.00130 (6)0.00126 (7)
S10.02389 (18)0.01886 (16)0.02601 (19)0.00422 (14)0.00848 (15)0.00549 (15)
S20.01462 (15)0.01936 (16)0.02128 (17)0.00053 (13)0.00044 (13)0.00356 (13)
F10.0604 (8)0.0447 (6)0.0310 (6)0.0010 (6)0.0109 (6)0.0045 (5)
F20.0657 (9)0.0673 (9)0.0477 (7)0.0240 (8)0.0279 (7)0.0101 (7)
F30.1059 (12)0.0556 (8)0.0218 (5)0.0375 (8)0.0000 (7)0.0077 (5)
F40.0245 (5)0.0205 (5)0.0518 (6)0.0056 (4)0.0024 (4)0.0024 (4)
F50.0218 (5)0.0381 (6)0.0487 (7)0.0011 (4)0.0069 (5)0.0178 (5)
F60.0240 (5)0.0599 (7)0.0393 (6)0.0006 (5)0.0130 (5)0.0160 (5)
O10.0143 (5)0.0183 (5)0.0281 (6)0.0022 (4)0.0050 (4)0.0038 (4)
O20.0214 (5)0.0221 (5)0.0430 (7)0.0034 (4)0.0033 (5)0.0172 (5)
O30.0216 (5)0.0174 (4)0.0247 (5)0.0020 (4)0.0049 (5)0.0036 (4)
O40.0256 (6)0.0321 (6)0.0255 (6)0.0102 (5)0.0054 (5)0.0011 (5)
O50.0388 (7)0.0271 (6)0.0548 (9)0.0032 (6)0.0144 (6)0.0156 (6)
O60.0192 (5)0.0192 (5)0.0226 (5)0.0024 (4)0.0044 (4)0.0008 (4)
O70.0268 (6)0.0249 (5)0.0380 (6)0.0042 (5)0.0044 (5)0.0128 (5)
O80.0265 (6)0.0382 (7)0.0226 (6)0.0057 (5)0.0033 (5)0.0054 (5)
N10.0151 (5)0.0136 (5)0.0172 (5)0.0001 (4)0.0006 (4)0.0024 (5)
N20.0163 (6)0.0154 (5)0.0203 (6)0.0018 (4)0.0008 (5)0.0020 (5)
C10.0161 (6)0.0150 (5)0.0184 (6)0.0008 (5)0.0022 (5)0.0028 (5)
C20.0208 (7)0.0185 (7)0.0299 (8)0.0015 (6)0.0080 (6)0.0053 (6)
C30.0140 (6)0.0173 (6)0.0186 (7)0.0010 (5)0.0008 (5)0.0000 (5)
C40.0153 (6)0.0160 (6)0.0285 (8)0.0022 (5)0.0001 (6)0.0046 (6)
C50.0191 (7)0.0177 (6)0.0240 (7)0.0013 (5)0.0021 (6)0.0041 (6)
C60.0229 (8)0.0342 (9)0.0422 (10)0.0021 (7)0.0045 (7)0.0205 (8)
C70.0192 (7)0.0177 (6)0.0219 (7)0.0016 (5)0.0015 (6)0.0066 (6)
C80.0167 (6)0.0148 (5)0.0202 (6)0.0003 (5)0.0006 (6)0.0010 (5)
C90.0357 (9)0.0181 (7)0.0272 (8)0.0020 (6)0.0004 (7)0.0046 (6)
C100.0227 (7)0.0238 (7)0.0252 (8)0.0050 (6)0.0040 (6)0.0011 (6)
C110.0206 (7)0.0180 (6)0.0254 (8)0.0029 (5)0.0037 (6)0.0009 (5)
C120.0251 (8)0.0262 (7)0.0325 (9)0.0083 (6)0.0040 (6)0.0039 (6)
C130.0238 (7)0.0244 (7)0.0266 (8)0.0048 (6)0.0023 (6)0.0027 (6)
C140.0202 (7)0.0150 (6)0.0347 (9)0.0026 (5)0.0045 (6)0.0002 (6)
C150.0208 (7)0.0159 (6)0.0285 (8)0.0017 (5)0.0047 (6)0.0036 (6)
C160.0264 (8)0.0192 (7)0.0286 (8)0.0027 (6)0.0031 (7)0.0015 (6)
C170.0283 (8)0.0272 (8)0.0309 (9)0.0083 (6)0.0023 (7)0.0025 (7)
C180.0307 (8)0.0304 (8)0.0234 (8)0.0046 (7)0.0007 (7)0.0041 (7)
C190.0370 (9)0.0225 (7)0.0227 (8)0.0021 (7)0.0025 (7)0.0010 (6)
C200.0294 (8)0.0190 (7)0.0280 (8)0.0048 (6)0.0053 (7)0.0020 (6)
C210.0164 (7)0.0227 (7)0.0359 (9)0.0039 (6)0.0042 (7)0.0084 (7)
C220.0174 (7)0.0281 (7)0.0267 (8)0.0021 (6)0.0063 (6)0.0089 (7)
C230.0246 (8)0.0393 (9)0.0258 (8)0.0064 (7)0.0034 (6)0.0093 (7)
C240.0336 (9)0.0515 (12)0.0203 (8)0.0062 (8)0.0028 (7)0.0027 (7)
C250.0368 (10)0.0384 (9)0.0260 (9)0.0062 (8)0.0125 (7)0.0043 (7)
C260.0252 (8)0.0334 (9)0.0374 (10)0.0064 (7)0.0092 (7)0.0096 (8)
C270.0182 (6)0.0327 (8)0.0342 (8)0.0029 (6)0.0036 (7)0.0081 (7)
C280.0471 (11)0.0350 (9)0.0242 (9)0.0160 (8)0.0097 (8)0.0035 (7)
C290.0174 (6)0.0197 (6)0.0249 (7)0.0010 (6)0.0020 (6)0.0001 (6)
O100.0248 (6)0.0246 (5)0.0277 (6)0.0010 (4)0.0032 (5)0.0025 (5)
C300.0532 (12)0.0274 (9)0.0428 (11)0.0109 (9)0.0023 (10)0.0036 (8)
C310.0244 (9)0.0427 (10)0.0425 (11)0.0027 (8)0.0027 (8)0.0149 (9)
C320.0642 (15)0.0383 (10)0.0290 (10)0.0173 (10)0.0082 (9)0.0019 (8)
C330.0487 (12)0.0284 (9)0.0295 (9)0.0095 (8)0.0045 (8)0.0058 (7)
Geometric parameters (Å, º) top
Cu1—N21.9344 (12)C11—C121.532 (2)
Cu1—N11.9471 (12)C11—H111.0000
Cu1—O61.9598 (10)C12—H12A0.9800
Cu1—O32.0183 (11)C12—H12B0.9800
S1—O51.4210 (13)C12—H12C0.9800
S1—O41.4340 (12)C13—H13A0.9800
S1—O31.4802 (11)C13—H13B0.9800
S1—C281.827 (2)C13—H13C0.9800
S2—O81.4283 (12)C14—C151.501 (2)
S2—O71.4322 (12)C14—H14A0.9900
S2—O61.4718 (11)C14—H14B0.9900
S2—C291.8341 (16)C15—C161.396 (2)
F1—C281.328 (2)C15—C201.403 (2)
F2—C281.325 (2)C16—C171.376 (2)
F3—C281.325 (2)C16—H160.9500
F4—C291.3166 (17)C17—C181.393 (2)
F5—C291.3270 (18)C17—H170.9500
F6—C291.3320 (18)C18—C191.397 (2)
O1—C31.3335 (17)C18—H180.9500
O1—C21.4554 (18)C19—C201.378 (3)
O2—C51.3432 (17)C19—H190.9500
O2—C61.471 (2)C20—H200.9500
N1—C31.2750 (18)C21—C221.515 (2)
N1—C11.4923 (17)C21—H21A0.9900
N2—C51.2734 (19)C21—H21B0.9900
N2—C71.4946 (18)C22—C271.389 (2)
C1—C81.5347 (19)C22—C231.395 (2)
C1—C21.537 (2)C23—C241.386 (3)
C1—H11.0000C23—H230.9500
C2—H2A0.9900C24—C251.397 (3)
C2—H2B0.9900C24—H240.9500
C3—C41.509 (2)C25—C261.383 (3)
C4—C51.503 (2)C25—H250.9500
C4—C211.559 (2)C26—C271.388 (3)
C4—C141.573 (2)C26—H260.9500
C6—C71.526 (2)C27—H270.9500
C6—H6A0.9900O10—C331.429 (2)
C6—H6B0.9900O10—C301.432 (2)
C7—C111.530 (2)C30—C311.507 (3)
C7—H71.0000C30—H30A0.9900
C8—C91.525 (2)C30—H30B0.9900
C8—C101.525 (2)C31—C321.521 (3)
C8—H81.0000C31—H31A0.9900
C9—H9A0.9800C31—H31B0.9900
C9—H9B0.9800C32—C331.508 (3)
C9—H9C0.9800C32—H32A0.9900
C10—H10A0.9800C32—H32B0.9900
C10—H10B0.9800C33—H33A0.9900
C10—H10C0.9800C33—H33B0.9900
C11—C131.528 (2)
N2—Cu1—N192.07 (5)H12B—C12—H12C109.5
N2—Cu1—O6157.99 (5)C11—C13—H13A109.5
N1—Cu1—O698.95 (5)C11—C13—H13B109.5
N2—Cu1—O391.46 (5)H13A—C13—H13B109.5
N1—Cu1—O3155.85 (5)C11—C13—H13C109.5
O6—Cu1—O386.25 (5)H13A—C13—H13C109.5
O5—S1—O4118.48 (8)H13B—C13—H13C109.5
O5—S1—O3114.14 (8)C15—C14—C4115.27 (12)
O4—S1—O3110.94 (7)C15—C14—H14A108.5
O5—S1—C28104.77 (9)C4—C14—H14A108.5
O4—S1—C28103.95 (8)C15—C14—H14B108.5
O3—S1—C28102.42 (7)C4—C14—H14B108.5
O8—S2—O7118.32 (8)H14A—C14—H14B107.5
O8—S2—O6113.83 (7)C16—C15—C20117.73 (16)
O7—S2—O6112.02 (7)C16—C15—C14121.04 (15)
O8—S2—C29104.53 (7)C20—C15—C14121.22 (14)
O7—S2—C29103.30 (7)C17—C16—C15121.27 (15)
O6—S2—C29102.56 (7)C17—C16—H16119.4
C3—O1—C2107.04 (11)C15—C16—H16119.4
C5—O2—C6105.85 (12)C16—C17—C18120.48 (15)
S1—O3—Cu1107.78 (6)C16—C17—H17119.8
S2—O6—Cu1137.79 (7)C18—C17—H17119.8
C3—N1—C1108.46 (11)C17—C18—C19119.11 (16)
C3—N1—Cu1126.80 (10)C17—C18—H18120.4
C1—N1—Cu1124.73 (9)C19—C18—H18120.4
C5—N2—C7108.54 (12)C20—C19—C18120.02 (16)
C5—N2—Cu1127.90 (10)C20—C19—H19120.0
C7—N2—Cu1123.55 (9)C18—C19—H19120.0
N1—C1—C8113.28 (11)C19—C20—C15121.35 (15)
N1—C1—C2102.32 (11)C19—C20—H20119.3
C8—C1—C2114.47 (12)C15—C20—H20119.3
N1—C1—H1108.8C22—C21—C4115.26 (12)
C8—C1—H1108.8C22—C21—H21A108.5
C2—C1—H1108.8C4—C21—H21A108.5
O1—C2—C1104.79 (11)C22—C21—H21B108.5
O1—C2—H2A110.8C4—C21—H21B108.5
C1—C2—H2A110.8H21A—C21—H21B107.5
O1—C2—H2B110.8C27—C22—C23118.24 (16)
C1—C2—H2B110.8C27—C22—C21120.06 (15)
H2A—C2—H2B108.9C23—C22—C21121.70 (15)
N1—C3—O1117.35 (12)C24—C23—C22120.77 (16)
N1—C3—C4130.40 (13)C24—C23—H23119.6
O1—C3—C4112.20 (12)C22—C23—H23119.6
C5—C4—C3112.72 (12)C23—C24—C25120.15 (18)
C5—C4—C21111.36 (13)C23—C24—H24119.9
C3—C4—C21108.75 (12)C25—C24—H24119.9
C5—C4—C14107.82 (12)C26—C25—C24119.54 (18)
C3—C4—C14108.19 (12)C26—C25—H25120.2
C21—C4—C14107.83 (12)C24—C25—H25120.2
N2—C5—O2116.40 (14)C25—C26—C27119.77 (16)
N2—C5—C4129.40 (13)C25—C26—H26120.1
O2—C5—C4114.04 (12)C27—C26—H26120.1
O2—C6—C7103.83 (12)C26—C27—C22121.53 (17)
O2—C6—H6A111.0C26—C27—H27119.2
C7—C6—H6A111.0C22—C27—H27119.2
O2—C6—H6B111.0F2—C28—F3108.05 (16)
C7—C6—H6B111.0F2—C28—F1107.35 (15)
H6A—C6—H6B109.0F3—C28—F1107.70 (18)
N2—C7—C6101.17 (12)F2—C28—S1111.55 (15)
N2—C7—C11111.35 (12)F3—C28—S1110.60 (13)
C6—C7—C11113.06 (13)F1—C28—S1111.42 (12)
N2—C7—H7110.3F4—C29—F5107.62 (13)
C6—C7—H7110.3F4—C29—F6108.02 (13)
C11—C7—H7110.3F5—C29—F6107.82 (12)
C9—C8—C10111.97 (12)F4—C29—S2112.14 (10)
C9—C8—C1108.49 (12)F5—C29—S2111.63 (10)
C10—C8—C1113.56 (12)F6—C29—S2109.44 (11)
C9—C8—H8107.5C33—O10—C30108.83 (14)
C10—C8—H8107.5O10—C30—C31107.32 (16)
C1—C8—H8107.5O10—C30—H30A110.3
C8—C9—H9A109.5C31—C30—H30A110.3
C8—C9—H9B109.5O10—C30—H30B110.3
H9A—C9—H9B109.5C31—C30—H30B110.3
C8—C9—H9C109.5H30A—C30—H30B108.5
H9A—C9—H9C109.5C30—C31—C32101.84 (16)
H9B—C9—H9C109.5C30—C31—H31A111.4
C8—C10—H10A109.5C32—C31—H31A111.4
C8—C10—H10B109.5C30—C31—H31B111.4
H10A—C10—H10B109.5C32—C31—H31B111.4
C8—C10—H10C109.5H31A—C31—H31B109.3
H10A—C10—H10C109.5C33—C32—C31101.42 (16)
H10B—C10—H10C109.5C33—C32—H32A111.5
C13—C11—C7112.04 (12)C31—C32—H32A111.5
C13—C11—C12110.60 (13)C33—C32—H32B111.5
C7—C11—C12108.93 (13)C31—C32—H32B111.5
C13—C11—H11108.4H32A—C32—H32B109.3
C7—C11—H11108.4O10—C33—C32105.12 (14)
C12—C11—H11108.4O10—C33—H33A110.7
C11—C12—H12A109.5C32—C33—H33A110.7
C11—C12—H12B109.5O10—C33—H33B110.7
H12A—C12—H12B109.5C32—C33—H33B110.7
C11—C12—H12C109.5H33A—C33—H33B108.8
H12A—C12—H12C109.5
O5—S1—O3—Cu1133.43 (8)O2—C6—C7—N219.77 (17)
O4—S1—O3—Cu13.54 (9)O2—C6—C7—C1199.40 (15)
C28—S1—O3—Cu1113.95 (8)N1—C1—C8—C9172.39 (12)
N2—Cu1—O3—S1117.04 (7)C2—C1—C8—C970.80 (16)
N1—Cu1—O3—S118.71 (15)N1—C1—C8—C1062.42 (16)
O6—Cu1—O3—S184.88 (7)C2—C1—C8—C1054.39 (16)
O8—S2—O6—Cu18.89 (13)N2—C7—C11—C1346.52 (17)
O7—S2—O6—Cu1146.45 (10)C6—C7—C11—C13159.63 (14)
C29—S2—O6—Cu1103.41 (10)N2—C7—C11—C12169.21 (12)
N2—Cu1—O6—S250.49 (19)C6—C7—C11—C1277.68 (17)
N1—Cu1—O6—S268.64 (11)C5—C4—C14—C1562.29 (16)
O3—Cu1—O6—S2135.09 (10)C3—C4—C14—C1559.89 (17)
N2—Cu1—N1—C33.27 (13)C21—C4—C14—C15177.35 (13)
O6—Cu1—N1—C3164.15 (12)C4—C14—C15—C16102.73 (17)
O3—Cu1—N1—C394.94 (16)C4—C14—C15—C2076.49 (19)
N2—Cu1—N1—C1178.11 (11)C20—C15—C16—C170.9 (2)
O6—Cu1—N1—C117.23 (11)C14—C15—C16—C17178.34 (15)
O3—Cu1—N1—C183.68 (15)C15—C16—C17—C181.0 (3)
N1—Cu1—N2—C56.91 (14)C16—C17—C18—C191.7 (3)
O6—Cu1—N2—C5127.21 (15)C17—C18—C19—C200.5 (3)
O3—Cu1—N2—C5149.20 (14)C18—C19—C20—C151.4 (3)
N1—Cu1—N2—C7173.13 (12)C16—C15—C20—C192.1 (2)
O6—Cu1—N2—C752.8 (2)C14—C15—C20—C19177.15 (15)
O3—Cu1—N2—C730.77 (12)C5—C4—C21—C2278.31 (16)
C3—N1—C1—C8122.31 (13)C3—C4—C21—C2246.50 (18)
Cu1—N1—C1—C856.52 (15)C14—C4—C21—C22163.59 (13)
C3—N1—C1—C21.43 (15)C4—C21—C22—C27113.08 (16)
Cu1—N1—C1—C2179.73 (10)C4—C21—C22—C2367.2 (2)
C3—O1—C2—C11.83 (15)C27—C22—C23—C241.0 (2)
N1—C1—C2—O11.92 (14)C21—C22—C23—C24179.23 (15)
C8—C1—C2—O1121.02 (13)C22—C23—C24—C251.1 (3)
C1—N1—C3—O10.33 (18)C23—C24—C25—C260.2 (3)
Cu1—N1—C3—O1179.13 (9)C24—C25—C26—C270.7 (3)
C1—N1—C3—C4177.82 (14)C25—C26—C27—C220.8 (2)
Cu1—N1—C3—C43.4 (2)C23—C22—C27—C260.1 (2)
C2—O1—C3—N11.02 (18)C21—C22—C27—C26179.83 (15)
C2—O1—C3—C4176.92 (12)O5—S1—C28—F251.17 (15)
N1—C3—C4—C54.6 (2)O4—S1—C28—F2176.17 (13)
O1—C3—C4—C5177.85 (13)O3—S1—C28—F268.25 (14)
N1—C3—C4—C21128.56 (17)O5—S1—C28—F369.12 (16)
O1—C3—C4—C2153.85 (16)O4—S1—C28—F355.89 (16)
N1—C3—C4—C14114.57 (17)O3—S1—C28—F3171.47 (14)
O1—C3—C4—C1463.02 (16)O5—S1—C28—F1171.12 (13)
C7—N2—C5—O26.04 (19)O4—S1—C28—F163.87 (14)
Cu1—N2—C5—O2173.93 (11)O3—S1—C28—F151.71 (14)
C7—N2—C5—C4168.98 (15)O8—S2—C29—F450.29 (13)
Cu1—N2—C5—C411.1 (2)O7—S2—C29—F4174.68 (11)
C6—O2—C5—N27.8 (2)O6—S2—C29—F468.74 (12)
C6—O2—C5—C4176.44 (14)O8—S2—C29—F5171.15 (11)
C3—C4—C5—N28.6 (2)O7—S2—C29—F564.46 (12)
C21—C4—C5—N2131.13 (17)O6—S2—C29—F552.12 (12)
C14—C4—C5—N2110.76 (18)O8—S2—C29—F669.57 (12)
C3—C4—C5—O2176.30 (13)O7—S2—C29—F654.83 (12)
C21—C4—C5—O253.75 (17)O6—S2—C29—F6171.40 (10)
C14—C4—C5—O264.36 (17)C33—O10—C30—C312.2 (2)
C5—O2—C6—C717.44 (18)O10—C30—C31—C3225.1 (2)
C5—N2—C7—C616.30 (17)C30—C31—C32—C3337.1 (2)
Cu1—N2—C7—C6163.67 (11)C30—O10—C33—C3222.2 (2)
C5—N2—C7—C11104.09 (15)C31—C32—C33—O1037.1 (2)
Cu1—N2—C7—C1175.94 (15)
 

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