#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:20:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178809 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/63/4106314.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4106314
loop_
_publ_author_name
'Ilya Popov'
'Sergey Lindeman'
'Olafs Daugulis'
_publ_section_title
;
 Copper-Catalyzed Arylation of 1H-Perfluoroalkanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9286
_journal_page_last               9289
_journal_paper_doi               10.1021/ja2041942
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C2 Cl Cu F5, K, 3(C6 H12 N2 O)'
_chemical_formula_sum            'C20 H36 Cl Cu F5 K N6 O3'
_chemical_formula_weight         641.64
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-01-06
_audit_creation_method
;
  Olex2 1.1-beta
  (compiled 2010.12.31 svn.r1581, GUI svn.r3426)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   26.038(4)
_cell_length_b                   26.038(4)
_cell_length_c                   21.702(4)
_cell_measurement_reflns_used    8129
_cell_measurement_temperature    223.15
_cell_measurement_theta_max      2.57
_cell_measurement_theta_min      24.89
_cell_volume                     12742(4)
_computing_cell_refinement       'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_data_collection       'APEX2 v1.0-27 (Bruker-Nonius, 2005)'
_computing_data_reduction        'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'smtbx-flip (Bourhis, 2008)'
_diffrn_ambient_temperature      223.15
_diffrn_detector_area_resol_mean 4K
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9105
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.56
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SAINT v7.12A'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       'hexagonal column'
_exptl_crystal_F_000             5976
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.335
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0847P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                4279
_reflns_number_total             4994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2041942_si_002.cif
_cod_data_source_block           olaf
_cod_database_code               4106314
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 'x+2/3, y+1/3, z+1/3'
5 '-y+2/3, x-y+1/3, z+1/3'
6 '-x+y+2/3, -x+1/3, z+1/3'
7 'x+1/3, y+2/3, z+2/3'
8 '-y+1/3, x-y+2/3, z+2/3'
9 '-x+y+1/3, -x+2/3, z+2/3'
10 '-x, -y, -z'
11 'y, -x+y, -z'
12 'x-y, x, -z'
13 '-x+2/3, -y+1/3, -z+1/3'
14 'y+2/3, -x+y+1/3, -z+1/3'
15 'x-y+2/3, x+1/3, -z+1/3'
16 '-x+1/3, -y+2/3, -z+2/3'
17 'y+1/3, -x+y+2/3, -z+2/3'
18 'x-y+1/3, x+2/3, -z+2/3'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.59462(3) 0.98346(3) 0.25845(3) 0.0525(2) Uani 1 1 d .
Cl1 Cl 0.52056(6) 0.99454(7) 0.25893(9) 0.0685(5) Uani 1 1 d .
F1 F 0.6706(2) 0.9475(3) 0.3096(3) 0.136(2) Uani 1 1 d .
F2 F 0.6639(2) 0.9363(2) 0.2109(3) 0.120(2) Uani 1 1 d .
F3 F 0.76648(15) 1.01868(19) 0.24756(19) 0.0770(11) Uani 1 1 d .
F4 F 0.72977(19) 1.0649(2) 0.2945(3) 0.121(2) Uani 1 1 d .
F5 F 0.7210(2) 1.0545(3) 0.1970(3) 0.133(2) Uani 1 1 d .
C19 C 0.6629(3) 0.9738(3) 0.2585(3) 0.0671(16) Uani 1 1 d .
C20 C 0.7193(3) 1.0262(3) 0.2495(3) 0.0639(16) Uani 1 1 d .
K1 K 1.0000 1.0000 0.5000 0.0257(4) Uani 1 6 d S
K2 K 1.0000 1.0000 0.33471(5) 0.0256(3) Uani 1 3 d S
K3 K 1.0000 1.0000 0.16565(6) 0.0281(3) Uani 1 3 d S
K4 K 1.0000 1.0000 0.0000 0.0284(4) Uani 1 6 d S
O1 O 0.90691(13) 0.96789(14) 0.41751(13) 0.0335(7) Uani 1 1 d .
O2 O 0.92206(13) 0.91266(14) 0.25171(14) 0.0404(8) Uani 1 1 d .
O3 O 0.93278(13) 1.02551(15) 0.08191(13) 0.0403(7) Uani 1 1 d .
N1 N 0.80621(17) 0.91967(17) 0.41626(18) 0.0382(9) Uani 1 1 d .
N2 N 0.86158(16) 1.02253(17) 0.41947(18) 0.0379(9) Uani 1 1 d .
N3 N 0.85115(18) 0.81640(18) 0.25365(17) 0.0402(9) Uani 1 1 d .
N4 N 0.82599(18) 0.89025(18) 0.2453(2) 0.0431(10) Uani 1 1 d .
N5 N 0.83213(17) 0.97303(17) 0.07725(16) 0.0369(8) Uani 1 1 d .
N6 N 0.88325(17) 1.07596(16) 0.08403(17) 0.0367(9) Uani 1 1 d .
C1 C 0.86025(19) 0.9699(2) 0.41726(18) 0.0304(9) Uani 1 1 d .
C2 C 0.7503(2) 0.9190(2) 0.4177(2) 0.0469(12) Uani 1 1 d .
H2A H 0.7216 0.8851 0.4423 0.056 Uiso 1 1 calc R
H2B H 0.7346 0.9141 0.3757 0.056 Uiso 1 1 calc R
C3 C 0.7570(2) 0.9746(2) 0.4446(3) 0.0524(13) Uani 1 1 d .
H3A H 0.7630 0.9748 0.4892 0.063 Uiso 1 1 calc R
H3B H 0.7207 0.9762 0.4374 0.063 Uiso 1 1 calc R
C4 C 0.8083(2) 1.0277(2) 0.4165(3) 0.0488(12) Uani 1 1 d .
H4A H 0.7994 1.0315 0.3735 0.059 Uiso 1 1 calc R
H4B H 0.8152 1.0634 0.4386 0.059 Uiso 1 1 calc R
C5 C 0.8038(2) 0.8628(2) 0.4119(3) 0.0493(12) Uani 1 1 d .
H5A H 0.8190 0.8554 0.4497 0.074 Uiso 1 1 calc R
H5B H 0.8277 0.8634 0.3774 0.074 Uiso 1 1 calc R
H5C H 0.7630 0.8316 0.4058 0.074 Uiso 1 1 calc R
C6 C 0.9190(2) 1.0771(2) 0.4199(2) 0.0402(10) Uani 1 1 d .
H6A H 0.9396 1.0794 0.4580 0.060 Uiso 1 1 calc R
H6B H 0.9130 1.1109 0.4170 0.060 Uiso 1 1 calc R
H6C H 0.9424 1.0771 0.3852 0.060 Uiso 1 1 calc R
C7 C 0.86819(19) 0.87456(18) 0.24992(18) 0.0306(9) Uani 1 1 d .
C8 C 0.7885(2) 0.7696(2) 0.2533(2) 0.0513(13) Uani 1 1 d .
H8A H 0.7739 0.7603 0.2958 0.062 Uiso 1 1 calc R
H8B H 0.7847 0.7336 0.2347 0.062 Uiso 1 1 calc R
C9 C 0.7518(2) 0.7893(2) 0.2175(3) 0.0552(13) Uani 1 1 d .
H9A H 0.7097 0.7595 0.2212 0.066 Uiso 1 1 calc R
H9B H 0.7627 0.7933 0.1738 0.066 Uiso 1 1 calc R
C10 C 0.7624(2) 0.8483(3) 0.2424(3) 0.0560(14) Uani 1 1 d .
H10A H 0.7433 0.8640 0.2154 0.067 Uiso 1 1 calc R
H10B H 0.7450 0.8428 0.2836 0.067 Uiso 1 1 calc R
C11 C 0.8934(2) 0.7963(2) 0.2591(2) 0.0516(12) Uani 1 1 d .
H11A H 0.9327 0.8286 0.2491 0.077 Uiso 1 1 calc R
H11B H 0.8828 0.7636 0.2309 0.077 Uiso 1 1 calc R
H11C H 0.8932 0.7832 0.3010 0.077 Uiso 1 1 calc R
C12 C 0.8438(3) 0.9518(2) 0.2493(2) 0.0482(12) Uani 1 1 d .
H12A H 0.8783 0.9718 0.2759 0.072 Uiso 1 1 calc R
H12B H 0.8116 0.9559 0.2663 0.072 Uiso 1 1 calc R
H12C H 0.8536 0.9693 0.2086 0.072 Uiso 1 1 calc R
C13 C 0.88444(19) 1.0253(2) 0.08129(17) 0.0314(10) Uani 1 1 d .
C14 C 0.7747(2) 0.9710(2) 0.0831(2) 0.0462(11) Uani 1 1 d .
H14A H 0.7645 0.9696 0.1268 0.055 Uiso 1 1 calc R
H14B H 0.7436 0.9351 0.0631 0.055 Uiso 1 1 calc R
C15 C 0.7784(2) 1.0250(2) 0.0534(2) 0.0482(12) Uani 1 1 d .
H15A H 0.7850 1.0246 0.0090 0.058 Uiso 1 1 calc R
H15B H 0.7412 1.0250 0.0596 0.058 Uiso 1 1 calc R
C16 C 0.8287(2) 1.0794(2) 0.0818(2) 0.0454(11) Uani 1 1 d .
H16A H 0.8360 1.1143 0.0578 0.055 Uiso 1 1 calc R
H16B H 0.8178 1.0842 0.1237 0.055 Uiso 1 1 calc R
C17 C 0.8330(2) 0.9177(2) 0.0803(2) 0.0492(12) Uani 1 1 d .
H17A H 0.8653 0.9208 0.0554 0.074 Uiso 1 1 calc R
H17B H 0.7957 0.8856 0.0649 0.074 Uiso 1 1 calc R
H17C H 0.8384 0.9097 0.1228 0.074 Uiso 1 1 calc R
C18 C 0.9381(2) 1.1320(2) 0.0892(3) 0.0532(13) Uani 1 1 d .
H18A H 0.9593 1.1412 0.0504 0.080 Uiso 1 1 calc R
H18B H 0.9624 1.1294 0.1216 0.080 Uiso 1 1 calc R
H18C H 0.9292 1.1631 0.0992 0.080 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C19 Cu1 Cl1 179.5(2) . .
F1 C19 Cu1 116.4(5) . .
F1 C19 F2 100.8(6) . .
F1 C19 C20 104.5(6) . .
F2 C19 Cu1 115.1(5) . .
F2 C19 C20 101.0(6) . .
C20 C19 Cu1 116.8(5) . .
F3 C20 F5 105.8(5) . .
F3 C20 C19 116.3(6) . .
F4 C20 F3 106.2(5) . .
F4 C20 F5 105.6(6) . .
F4 C20 C19 110.3(6) . .
F5 C20 C19 111.9(6) . .
K2 K1 K2 180.0 . 10_776
O1 K1 K2 130.01(6) 3_675 10_776
O1 K1 K2 49.99(6) 12_656 10_776
O1 K1 K2 130.01(6) 2_765 10_776
O1 K1 K2 49.99(6) 11_566 10_776
O1 K1 K2 49.99(6) 10_776 10_776
O1 K1 K2 130.01(6) . 10_776
O1 K1 K2 49.99(6) 3_675 .
O1 K1 K2 130.01(6) 12_656 .
O1 K1 K2 49.99(6) 2_765 .
O1 K1 K2 130.01(6) 11_566 .
O1 K1 K2 130.01(6) 10_776 .
O1 K1 K2 49.99(6) . .
O1 K1 O1 83.10(8) 2_765 3_675
O1 K1 O1 96.90(8) 11_566 3_675
O1 K1 O1 96.90(8) 10_776 3_675
O1 K1 O1 83.10(8) . 3_675
O1 K1 O1 96.90(8) 2_765 12_656
O1 K1 O1 83.10(8) 11_566 12_656
O1 K1 O1 83.10(8) 10_776 12_656
O1 K1 O1 83.10(8) 10_776 11_566
O1 K1 O1 180.00(9) 11_566 2_765
O1 K1 O1 96.90(8) 10_776 2_765
O1 K1 O1 180.00(11) 12_656 3_675
O1 K1 O1 96.90(8) . 12_656
O1 K1 O1 96.90(8) . 11_566
O1 K1 O1 180.0 . 10_776
O1 K1 O1 83.10(8) . 2_765
K1 K2 K3 180.0 . .
O1 K2 K1 49.88(6) . .
O1 K2 K1 49.88(6) 3_675 .
O1 K2 K1 49.88(6) 2_765 .
O1 K2 K3 130.12(6) . .
O1 K2 K3 130.12(6) 3_675 .
O1 K2 K3 130.12(6) 2_765 .
O1 K2 O1 82.94(9) . 2_765
O1 K2 O1 82.94(9) 3_675 2_765
O1 K2 O1 82.94(9) . 3_675
O1 K2 O2 90.15(9) 2_765 2_765
O1 K2 O2 104.64(9) 3_675 2_765
O1 K2 O2 90.15(9) 3_675 3_675
O1 K2 O2 169.10(10) 2_765 3_675
O1 K2 O2 169.10(10) . 2_765
O1 K2 O2 104.64(9) 2_765 .
O1 K2 O2 104.64(9) . 3_675
O1 K2 O2 90.15(9) . .
O1 K2 O2 169.10(10) 3_675 .
O2 K2 K1 129.80(7) 3_675 .
O2 K2 K1 129.80(7) . .
O2 K2 K1 129.80(7) 2_765 .
O2 K2 K3 50.20(7) . .
O2 K2 K3 50.20(7) 2_765 .
O2 K2 K3 50.20(7) 3_675 .
O2 K2 O2 83.42(10) 3_675 2_765
O2 K2 O2 83.42(10) . 2_765
O2 K2 O2 83.42(10) . 3_675
K4 K3 K2 180.0 . .
O2 K3 K2 49.18(6) 3_675 .
O2 K3 K2 49.18(6) 2_765 .
O2 K3 K2 49.18(6) . .
O2 K3 K4 130.82(6) . .
O2 K3 K4 130.82(6) 2_765 .
O2 K3 K4 130.82(6) 3_675 .
O2 K3 O2 81.90(9) . 3_675
O2 K3 O2 81.90(9) 2_765 3_675
O2 K3 O2 81.90(9) . 2_765
O3 K3 K2 130.07(6) 2_765 .
O3 K3 K2 130.07(6) 3_675 .
O3 K3 K2 130.07(6) . .
O3 K3 K4 49.93(6) 2_765 .
O3 K3 K4 49.93(6) 3_675 .
O3 K3 K4 49.93(6) . .
O3 K3 O2 88.30(9) . 3_675
O3 K3 O2 109.32(9) 3_675 3_675
O3 K3 O2 88.30(9) 3_675 2_765
O3 K3 O2 163.99(10) 2_765 3_675
O3 K3 O2 163.99(10) . 2_765
O3 K3 O2 109.32(9) 2_765 2_765
O3 K3 O2 163.99(10) 3_675 .
O3 K3 O2 88.30(9) 2_765 .
O3 K3 O2 109.32(9) . .
O3 K3 O3 83.01(10) . 3_675
O3 K3 O3 83.01(10) 2_765 3_675
O3 K3 O3 83.01(10) 2_765 .
K3 K4 K3 180.0 10_775 .
O3 K4 K3 129.45(6) 10_775 .
O3 K4 K3 50.55(6) . .
O3 K4 K3 50.55(6) 3_675 .
O3 K4 K3 129.45(6) 12_655 .
O3 K4 K3 50.55(6) 2_765 .
O3 K4 K3 129.45(6) 11_565 .
O3 K4 K3 50.55(6) 10_775 10_775
O3 K4 K3 129.45(6) . 10_775
O3 K4 K3 129.45(6) 3_675 10_775
O3 K4 K3 50.55(6) 12_655 10_775
O3 K4 K3 129.45(6) 2_765 10_775
O3 K4 K3 50.55(6) 11_565 10_775
O3 K4 O3 96.06(9) 3_675 10_775
O3 K4 O3 83.94(9) 12_655 10_775
O3 K4 O3 96.06(9) 2_765 10_775
O3 K4 O3 83.94(9) 11_565 10_775
O3 K4 O3 83.94(9) 3_675 .
O3 K4 O3 96.06(9) 12_655 .
O3 K4 O3 83.94(9) 2_765 .
O3 K4 O3 96.06(9) 2_765 12_655
O3 K4 O3 180.0 12_655 3_675
O3 K4 O3 83.94(9) 2_765 3_675
O3 K4 O3 180.0 . 10_775
O3 K4 O3 96.06(9) 11_565 .
O3 K4 O3 83.94(9) 11_565 12_655
O3 K4 O3 180.0 11_565 2_765
O3 K4 O3 96.06(9) 11_565 3_675
K1 O1 K2 80.13(8) . .
C1 O1 K1 135.5(3) . .
C1 O1 K2 134.9(3) . .
K2 O2 K3 80.62(8) . .
C7 O2 K2 137.0(3) . .
C7 O2 K3 132.9(3) . .
K4 O3 K3 79.52(8) . .
C13 O3 K3 138.1(3) . .
C13 O3 K4 137.5(3) . .
C1 N1 C2 124.1(4) . .
C1 N1 C5 118.5(4) . .
C2 N1 C5 117.3(4) . .
C1 N2 C4 123.1(4) . .
C1 N2 C6 118.7(4) . .
C6 N2 C4 117.9(4) . .
C7 N3 C8 122.4(4) . .
C7 N3 C11 122.0(4) . .
C11 N3 C8 115.6(4) . .
C7 N4 C10 124.5(4) . .
C7 N4 C12 118.4(4) . .
C12 N4 C10 116.9(4) . .
C13 N5 C14 121.3(4) . .
C13 N5 C17 119.0(4) . .
C17 N5 C14 118.5(4) . .
C13 N6 C16 124.0(4) . .
C13 N6 C18 120.1(4) . .
C18 N6 C16 115.9(4) . .
O1 C1 N1 121.5(4) . .
O1 C1 N2 120.8(4) . .
N2 C1 N1 117.7(4) . .
N1 C2 H2A 109.3 . .
N1 C2 H2B 109.3 . .
N1 C2 C3 111.6(4) . .
H2A C2 H2B 108.0 . .
C3 C2 H2A 109.3 . .
C3 C2 H2B 109.3 . .
C2 C3 H3A 109.4 . .
C2 C3 H3B 109.4 . .
C2 C3 C4 111.0(4) . .
H3A C3 H3B 108.0 . .
C4 C3 H3A 109.4 . .
C4 C3 H3B 109.4 . .
N2 C4 C3 110.4(4) . .
N2 C4 H4A 109.6 . .
N2 C4 H4B 109.6 . .
C3 C4 H4A 109.6 . .
C3 C4 H4B 109.6 . .
H4A C4 H4B 108.1 . .
N1 C5 H5A 109.5 . .
N1 C5 H5B 109.5 . .
N1 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N2 C6 H6A 109.5 . .
N2 C6 H6B 109.5 . .
N2 C6 H6C 109.5 . .
H6A C6 H6B 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
O2 C7 N3 119.8(4) . .
O2 C7 N4 121.4(4) . .
N3 C7 N4 118.8(4) . .
N3 C8 H8A 109.5 . .
N3 C8 H8B 109.5 . .
N3 C8 C9 110.5(4) . .
H8A C8 H8B 108.1 . .
C9 C8 H8A 109.5 . .
C9 C8 H8B 109.5 . .
C8 C9 H9A 109.7 . .
C8 C9 H9B 109.7 . .
C8 C9 C10 109.6(4) . .
H9A C9 H9B 108.2 . .
C10 C9 H9A 109.7 . .
C10 C9 H9B 109.7 . .
N4 C10 C9 109.6(4) . .
N4 C10 H10A 109.7 . .
N4 C10 H10B 109.7 . .
C9 C10 H10A 109.7 . .
C9 C10 H10B 109.7 . .
H10A C10 H10B 108.2 . .
N3 C11 H11A 109.5 . .
N3 C11 H11B 109.5 . .
N3 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N4 C12 H12A 109.5 . .
N4 C12 H12B 109.5 . .
N4 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O3 C13 N5 120.2(4) . .
O3 C13 N6 120.9(4) . .
N6 C13 N5 118.9(4) . .
N5 C14 H14A 109.7 . .
N5 C14 H14B 109.7 . .
N5 C14 C15 109.8(4) . .
H14A C14 H14B 108.2 . .
C15 C14 H14A 109.7 . .
C15 C14 H14B 109.7 . .
C14 C15 H15A 109.9 . .
C14 C15 H15B 109.9 . .
H15A C15 H15B 108.3 . .
C16 C15 C14 108.9(4) . .
C16 C15 H15A 109.9 . .
C16 C15 H15B 109.9 . .
N6 C16 C15 111.8(4) . .
N6 C16 H16A 109.3 . .
N6 C16 H16B 109.3 . .
C15 C16 H16A 109.3 . .
C15 C16 H16B 109.3 . .
H16A C16 H16B 107.9 . .
N5 C17 H17A 109.5 . .
N5 C17 H17B 109.5 . .
N5 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N6 C18 H18A 109.5 . .
N6 C18 H18B 109.5 . .
N6 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl1 2.0875(15) .
Cu1 C19 1.916(6) .
F1 C19 1.368(8) .
F2 C19 1.431(8) .
F3 C20 1.338(7) .
F4 C20 1.329(8) .
F5 C20 1.347(8) .
C19 C20 1.434(10) .
K1 O1 2.784(3) 10_776
K1 O1 2.784(3) 2_765
K1 O1 2.784(3) 11_566
K1 O1 2.784(3) 12_656
K1 O1 2.784(3) 3_675
K1 O1 2.784(3) .
K2 O1 2.789(3) 3_675
K2 O1 2.789(3) .
K2 O1 2.789(3) 2_765
K2 O2 2.814(3) .
K2 O2 2.814(3) 3_675
K2 O2 2.814(3) 2_765
K3 O2 2.857(3) 3_675
K3 O2 2.857(3) 2_765
K3 O2 2.857(3) .
K3 O3 2.823(3) 3_675
K3 O3 2.823(3) .
K3 O3 2.823(3) 2_765
K4 O3 2.797(3) 11_565
K4 O3 2.797(3) 2_765
K4 O3 2.798(3) 12_655
K4 O3 2.798(3) 10_775
K4 O3 2.798(3) .
K4 O3 2.798(3) 3_675
O1 C1 1.242(5) .
O2 C7 1.250(5) .
O3 C13 1.256(5) .
N1 C1 1.361(6) .
N1 C2 1.449(6) .
N1 C5 1.453(7) .
N2 C1 1.354(6) .
N2 C4 1.460(6) .
N2 C6 1.458(6) .
N3 C7 1.351(6) .
N3 C8 1.468(7) .
N3 C11 1.440(7) .
N4 C7 1.354(6) .
N4 C10 1.459(7) .
N4 C12 1.430(6) .
N5 C13 1.365(6) .
N5 C14 1.474(7) .
N5 C17 1.453(7) .
N6 C13 1.336(6) .
N6 C16 1.467(6) .
N6 C18 1.448(6) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 C3 1.487(7) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 C4 1.489(7) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C5 H5C 0.9700 .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C6 H6C 0.9700 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 C9 1.505(8) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 C10 1.519(8) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 H11C 0.9700 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 H12C 0.9700 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 C15 1.507(7) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 C16 1.498(7) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 H17C 0.9700 .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 H18C 0.9700 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
Cu1 C19 C20 F3 -177.8(5) .
Cu1 C19 C20 F4 61.3(7) .
Cu1 C19 C20 F5 -56.0(7) .
F1 C19 C20 F3 52.1(8) .
F1 C19 C20 F4 -68.8(7) .
F1 C19 C20 F5 173.9(5) .
F2 C19 C20 F3 -52.2(7) .
F2 C19 C20 F4 -173.1(5) .
F2 C19 C20 F5 69.6(7) .
K1 O1 C1 N1 -115.0(4) .
K1 O1 C1 N2 63.4(6) .
K2 O1 C1 N1 112.9(4) .
K2 O1 C1 N2 -68.7(6) .
K2 O2 C7 N3 -110.2(5) .
K2 O2 C7 N4 68.7(6) .
K3 O2 C7 N3 117.9(4) .
K3 O2 C7 N4 -63.2(6) .
K3 O3 C13 N5 -75.9(5) .
K3 O3 C13 N6 104.6(5) .
K4 O3 C13 N5 68.2(6) .
K4 O3 C13 N6 -111.3(5) .
O1 K1 O1 K2 138.08(3) 11_566
O1 K1 O1 K2 -41.92(3) 2_765
O1 K1 O1 K2 41.92(3) 3_675
O1 K1 O1 K2 -138.08(3) 12_656
O1 K1 O1 C1 -105.8(5) 3_675
O1 K1 O1 C1 74.2(5) 12_656
O1 K1 O1 C1 -9.7(4) 11_566
O1 K1 O1 C1 170.3(4) 2_765
O1 K2 O1 K1 41.86(4) 2_765
O1 K2 O1 K1 -41.86(4) 3_675
O1 K2 O1 C1 106.2(5) 3_675
O1 K2 O1 C1 -170.0(5) 2_765
O1 K2 O2 K3 146.77(9) .
O1 K2 O2 K3 96.3(5) 3_675
O1 K2 O2 K3 -130.48(8) 2_765
O1 K2 O2 C7 83.1(5) 2_765
O1 K2 O2 C7 -50.2(8) 3_675
O1 K2 O2 C7 0.3(5) .
O2 K2 O1 K1 146.59(9) .
O2 K2 O1 K1 -130.16(8) 3_675
O2 K2 O1 K1 92.9(5) 2_765
O2 K2 O1 C1 -65.3(4) .
O2 K2 O1 C1 17.9(4) 3_675
O2 K2 O1 C1 -119.0(6) 2_765
O2 K2 O2 K3 -42.05(4) 2_765
O2 K2 O2 K3 42.05(4) 3_675
O2 K2 O2 C7 -104.4(5) 3_675
O2 K2 O2 C7 171.5(5) 2_765
O2 K3 O2 K2 -41.45(3) 3_675
O2 K3 O2 K2 41.45(3) 2_765
O2 K3 O2 C7 107.6(5) 3_675
O2 K3 O2 C7 -169.5(4) 2_765
O2 K3 O3 K4 -127.61(8) .
O2 K3 O3 K4 99.5(3) 2_765
O2 K3 O3 K4 151.59(9) 3_675
O2 K3 O3 C13 28.6(5) .
O2 K3 O3 C13 -104.3(5) 2_765
O2 K3 O3 C13 -52.2(5) 3_675
O3 K3 O2 K2 94.2(3) 3_675
O3 K3 O2 K2 -126.77(9) .
O3 K3 O2 K2 151.24(9) 2_765
O3 K3 O2 C7 -116.7(5) 3_675
O3 K3 O2 C7 22.3(4) .
O3 K3 O2 C7 -59.7(4) 2_765
O3 K3 O3 K4 -41.89(4) 2_765
O3 K3 O3 K4 41.89(4) 3_675
O3 K3 O3 C13 114.3(5) 2_765
O3 K3 O3 C13 -161.9(5) 3_675
O3 K4 O3 K3 -137.74(4) 11_565
O3 K4 O3 K3 -42.26(4) 3_675
O3 K4 O3 K3 42.26(4) 2_765
O3 K4 O3 K3 137.74(4) 12_655
O3 K4 O3 C13 -114.2(5) 2_765
O3 K4 O3 C13 65.8(5) 11_565
O3 K4 O3 C13 -18.8(5) 12_655
O3 K4 O3 C13 161.2(5) 3_675
N1 C2 C3 C4 47.9(6) .
N3 C8 C9 C10 -53.6(6) .
N5 C14 C15 C16 -55.8(5) .
C1 N1 C2 C3 -22.4(7) .
C1 N2 C4 C3 31.0(7) .
C2 N1 C1 O1 178.1(4) .
C2 N1 C1 N2 -0.3(7) .
C2 C3 C4 N2 -51.7(6) .
C4 N2 C1 O1 177.2(4) .
C4 N2 C1 N1 -4.4(7) .
C5 N1 C1 O1 -3.4(7) .
C5 N1 C1 N2 178.1(4) .
C5 N1 C2 C3 159.1(4) .
C6 N2 C1 O1 2.2(6) .
C6 N2 C1 N1 -179.4(4) .
C6 N2 C4 C3 -154.0(4) .
C7 N3 C8 C9 29.1(7) .
C7 N4 C10 C9 -24.5(7) .
C8 N3 C7 O2 178.5(4) .
C8 N3 C7 N4 -0.4(6) .
C8 C9 C10 N4 51.1(6) .
C10 N4 C7 O2 179.3(4) .
C10 N4 C7 N3 -1.8(7) .
C11 N3 C7 O2 -0.6(6) .
C11 N3 C7 N4 -179.5(4) .
C11 N3 C8 C9 -151.8(4) .
C12 N4 C7 O2 -6.7(7) .
C12 N4 C7 N3 172.1(4) .
C12 N4 C10 C9 161.4(5) .
C13 N5 C14 C15 36.6(6) .
C13 N6 C16 C15 -21.1(6) .
C14 N5 C13 O3 173.4(4) .
C14 N5 C13 N6 -7.2(6) .
C14 C15 C16 N6 48.7(6) .
C16 N6 C13 O3 178.2(4) .
C16 N6 C13 N5 -1.3(7) .
C17 N5 C13 O3 6.5(6) .
C17 N5 C13 N6 -174.0(4) .
C17 N5 C14 C15 -156.5(4) .
C18 N6 C13 O3 -1.4(7) .
C18 N6 C13 N5 179.1(4) .
C18 N6 C16 C15 158.6(5) .
