#------------------------------------------------------------------------------
#$Date: 2019-11-26 16:29:30 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243634 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/94/4089408.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_4089408
loop_
_publ_author_name
'Hannigan, Steven F.'
'Lum, June S.'
'Bacon, Jeffrey W.'
'Moore, Curtis'
'Golen, James A.'
'Rheingold, Arnold L.'
'Doerrer, Linda H.'
_publ_section_title
;
 Room Temperature Stable Organocuprate Copper(III) Complex
;
_journal_issue                   12
_journal_name_full               Organometallics
_journal_page_first              3429
_journal_paper_doi               10.1021/om4000538
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C24 H33 Cu F18 K O9'
_chemical_formula_weight         910.14
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.1068(11)
_cell_length_b                   8.5756(4)
_cell_length_c                   18.6294(9)
_cell_measurement_reflns_used    8513
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.38
_cell_volume                     3531.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14706
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  0.8989
_exptl_absorpt_correction_T_min  0.7117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1836
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.479(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         5690
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.4600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                5499
_reflns_number_total             5690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4000538_si_002.cif
_cod_data_source_block           lhd290_compound_2_Cu3_ACIE
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               4089408
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
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 0.353787(11) 0.73955(3) 0.50451(2) 0.01917(8) Uani 1 1 d .
K1 K 0.47375(2) 0.36329(5) 0.49721(3) 0.02042(11) Uani 1 1 d .
F1 F 0.18115(8) 0.8848(3) 0.56515(10) 0.0510(5) Uani 1 1 d .
F2 F 0.17442(8) 0.8387(2) 0.67867(10) 0.0420(4) Uani 1 1 d .
F3 F 0.22664(9) 1.03284(18) 0.64063(11) 0.0488(5) Uani 1 1 d .
F4 F 0.27397(9) 0.7227(2) 0.74645(9) 0.0421(4) Uani 1 1 d .
F5 F 0.32425(9) 0.9198(2) 0.70927(10) 0.0489(5) Uani 1 1 d .
F6 F 0.35412(8) 0.6895(3) 0.68299(11) 0.0482(5) Uani 1 1 d .
F7 F 0.49530(14) 0.7906(3) 0.62142(12) 0.0688(7) Uani 1 1 d .
F8 F 0.54212(9) 0.6126(2) 0.56360(12) 0.0503(5) Uani 1 1 d .
F9 F 0.57285(9) 0.8504(2) 0.55848(13) 0.0556(6) Uani 1 1 d .
F10 F 0.56035(9) 0.8521(2) 0.41430(14) 0.0565(6) Uani 1 1 d .
F11 F 0.53479(9) 0.6112(2) 0.42093(12) 0.0535(6) Uani 1 1 d .
F12 F 0.47596(12) 0.7786(3) 0.36979(12) 0.0692(7) Uani 1 1 d .
F13 F 0.19213(10) 0.6638(3) 0.43668(11) 0.0641(7) Uani 1 1 d .
F14 F 0.17787(9) 0.7373(3) 0.32790(11) 0.0522(6) Uani 1 1 d .
F15 F 0.22671(10) 0.5244(2) 0.35019(12) 0.0609(6) Uani 1 1 d .
F16 F 0.27369(8) 0.8395(2) 0.25288(9) 0.0404(4) Uani 1 1 d .
F17 F 0.32326(10) 0.6316(2) 0.27717(9) 0.0474(5) Uani 1 1 d .
F18 F 0.35918(8) 0.8531(3) 0.30614(11) 0.0480(5) Uani 1 1 d .
O1 O 0.58548(9) 0.2814(2) 0.56620(11) 0.0261(4) Uani 1 1 d .
O2 O 0.57742(9) 0.2408(2) 0.41873(11) 0.0269(5) Uani 1 1 d .
O3 O 0.46967(9) 0.2885(2) 0.34748(12) 0.0296(5) Uani 1 1 d .
O4 O 0.36502(9) 0.2508(2) 0.43207(13) 0.0281(5) Uani 1 1 d .
O5 O 0.36891(8) 0.3266(2) 0.58120(11) 0.0298(5) Uani 1 1 d .
O6 O 0.48124(10) 0.2783(3) 0.64787(12) 0.0319(5) Uani 1 1 d .
O7 O 0.30434(8) 0.8436(2) 0.56691(10) 0.0245(4) Uani 1 1 d .
O8 O 0.43444(7) 0.67910(17) 0.50176(12) 0.0256(4) Uani 1 1 d .
O9 O 0.31629(9) 0.6799(2) 0.42103(11) 0.0315(4) Uani 1 1 d .
C1 C 0.63400(12) 0.2158(4) 0.52590(17) 0.0298(7) Uani 1 1 d .
H1A H 0.6295 0.1011 0.5232 0.036 Uiso 1 1 calc R
H1B H 0.6731 0.2396 0.5494 0.036 Uiso 1 1 calc R
C2 C 0.63260(13) 0.2837(4) 0.45299(18) 0.0318(7) Uani 1 1 d .
H2D H 0.6356 0.3987 0.4560 0.038 Uiso 1 1 calc R
H2E H 0.6674 0.2447 0.4247 0.038 Uiso 1 1 calc R
C3 C 0.57674(14) 0.2765(4) 0.34517(18) 0.0354(7) Uani 1 1 d .
H3A H 0.6120 0.2280 0.3212 0.042 Uiso 1 1 calc R
H3B H 0.5792 0.3908 0.3384 0.042 Uiso 1 1 calc R
C4 C 0.51903(15) 0.2153(4) 0.31294(17) 0.0370(7) Uani 1 1 d .
H4A H 0.5180 0.2380 0.2608 0.044 Uiso 1 1 calc R
H4B H 0.5166 0.1010 0.3195 0.044 Uiso 1 1 calc R
C5 C 0.41342(15) 0.2368(4) 0.31865(19) 0.0366(7) Uani 1 1 d .
H5A H 0.4109 0.1216 0.3213 0.044 Uiso 1 1 calc R
H5B H 0.4102 0.2681 0.2677 0.044 Uiso 1 1 calc R
C6 C 0.36282(13) 0.3081(4) 0.36098(19) 0.0367(8) Uani 1 1 d .
H6A H 0.3669 0.4231 0.3612 0.044 Uiso 1 1 calc R
H6B H 0.3235 0.2811 0.3388 0.044 Uiso 1 1 calc R
C7 C 0.31347(12) 0.3006(3) 0.47290(18) 0.0322(7) Uani 1 1 d .
H7A H 0.2761 0.2567 0.4517 0.039 Uiso 1 1 calc R
H7B H 0.3104 0.4158 0.4716 0.039 Uiso 1 1 calc R
C8 C 0.31979(13) 0.2471(3) 0.54821(19) 0.0304(7) Uani 1 1 d .
H8A H 0.2820 0.2685 0.5749 0.037 Uiso 1 1 calc R
H8B H 0.3272 0.1333 0.5492 0.037 Uiso 1 1 calc R
C9 C 0.37538(17) 0.2854(4) 0.6550(2) 0.0429(8) Uani 1 1 d .
H9A H 0.3761 0.1705 0.6599 0.051 Uiso 1 1 calc R
H9B H 0.3405 0.3258 0.6827 0.051 Uiso 1 1 calc R
C10 C 0.43255(14) 0.3523(4) 0.68401(17) 0.0417(8) Uani 1 1 d .
H10A H 0.4338 0.4662 0.6756 0.050 Uiso 1 1 calc R
H10B H 0.4353 0.3332 0.7363 0.050 Uiso 1 1 calc R
C11 C 0.53836(13) 0.3165(4) 0.67920(16) 0.0348(6) Uani 1 1 d .
H11A H 0.5390 0.2856 0.7304 0.042 Uiso 1 1 calc R
H11B H 0.5456 0.4302 0.6762 0.042 Uiso 1 1 calc R
C12 C 0.58622(14) 0.2302(3) 0.63865(17) 0.0310(7) Uani 1 1 d .
H12A H 0.6264 0.2507 0.6602 0.037 Uiso 1 1 calc R
H12B H 0.5784 0.1166 0.6409 0.037 Uiso 1 1 calc R
C13 C 0.21260(13) 0.8852(3) 0.62664(16) 0.0336(7) Uani 1 1 d .
C14 C 0.26835(14) 0.7787(3) 0.61967(16) 0.0242(6) Uani 1 1 d .
C15 C 0.30441(14) 0.7799(4) 0.69026(17) 0.0319(7) Uani 1 1 d .
C16 C 0.24801(13) 0.6122(3) 0.60439(15) 0.0290(6) Uani 1 1 d .
H16A H 0.2836 0.5446 0.6001 0.043 Uiso 1 1 calc R
H16B H 0.2250 0.6097 0.5595 0.043 Uiso 1 1 calc R
H16C H 0.2224 0.5752 0.6438 0.043 Uiso 1 1 calc R
C17 C 0.52288(16) 0.7610(3) 0.5601(2) 0.0367(8) Uani 1 1 d .
C18 C 0.48028(10) 0.7874(3) 0.49577(19) 0.0240(5) Uani 1 1 d .
C19 C 0.51364(16) 0.7570(4) 0.4252(2) 0.0371(8) Uani 1 1 d .
C20 C 0.45973(12) 0.9580(3) 0.4965(2) 0.0433(8) Uani 1 1 d .
H20A H 0.4325 0.9769 0.4560 0.065 Uiso 1 1 calc R
H20B H 0.4951 1.0263 0.4925 0.065 Uiso 1 1 calc R
H20C H 0.4384 0.9799 0.5416 0.065 Uiso 1 1 calc R
C21 C 0.21869(16) 0.6717(4) 0.37244(17) 0.0427(8) Uani 1 1 d .
C22 C 0.27787(14) 0.7637(3) 0.37747(16) 0.0241(6) Uani 1 1 d .
C23 C 0.30758(15) 0.7702(3) 0.30341(18) 0.0301(7) Uani 1 1 d .
C24 C 0.26503(13) 0.9301(3) 0.40143(15) 0.0293(6) Uani 1 1 d .
H24A H 0.3031 0.9882 0.4045 0.044 Uiso 1 1 calc R
H24B H 0.2455 0.9286 0.4486 0.044 Uiso 1 1 calc R
H24C H 0.2382 0.9806 0.3666 0.044 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'
O O 0.0106 0.0060 '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'
Cu Cu 0.3201 1.2651 '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_3
O7 Cu1 O9 113.88(9) .
O7 Cu1 O8 136.69(9) .
O9 Cu1 O8 109.42(10) .
O5 K1 O8 80.69(5) .
O5 K1 O4 60.40(6) .
O8 K1 O4 94.42(5) .
O5 K1 O3 119.38(6) .
O8 K1 O3 103.44(6) .
O4 K1 O3 58.98(6) .
O5 K1 O1 115.61(6) .
O8 K1 O1 118.83(6) .
O4 K1 O1 146.12(5) .
O3 K1 O1 114.10(6) .
O5 K1 F11 137.71(6) .
O8 K1 F11 57.13(5) .
O4 K1 F11 115.58(7) .
O3 K1 F11 72.58(6) .
O1 K1 F11 89.91(6) .
O5 K1 F8 105.95(6) .
O8 K1 F8 56.21(5) .
O4 K1 F8 150.33(5) .
O3 K1 F8 126.71(6) .
O1 K1 F8 62.65(5) .
F11 K1 F8 54.79(6) .
O5 K1 O6 58.78(6) .
O8 K1 O6 103.15(6) .
O4 K1 O6 111.92(7) .
O3 K1 O6 152.49(6) .
O1 K1 O6 57.12(6) .
F11 K1 O6 129.26(7) .
F8 K1 O6 75.10(6) .
O5 K1 O2 152.42(6) .
O8 K1 O2 126.74(5) .
O4 K1 O2 109.05(6) .
O3 K1 O2 57.00(6) .
O1 K1 O2 57.31(6) .
F11 K1 O2 69.61(5) .
F8 K1 O2 94.02(6) .
O6 K1 O2 110.46(6) .
O5 K1 C20 79.49(6) 1_545
O8 K1 C20 157.07(5) 1_545
O4 K1 C20 65.65(6) 1_545
O3 K1 C20 76.74(8) 1_545
O1 K1 C20 80.47(7) 1_545
F11 K1 C20 140.54(7) 1_545
F8 K1 C20 141.57(7) 1_545
O6 K1 C20 76.03(8) 1_545
O2 K1 C20 73.08(6) 1_545
C17 F8 K1 120.92(17) .
C19 F11 K1 119.68(18) .
C12 O1 C1 111.7(2) .
C12 O1 K1 120.74(17) .
C1 O1 K1 120.54(16) .
C3 O2 C2 112.9(2) .
C3 O2 K1 113.73(17) .
C2 O2 K1 110.81(17) .
C4 O3 C5 111.3(2) .
C4 O3 K1 121.22(17) .
C5 O3 K1 117.66(19) .
C6 O4 C7 111.4(2) .
C6 O4 K1 108.00(16) .
C7 O4 K1 110.00(16) .
C8 O5 C9 112.0(3) .
C8 O5 K1 116.24(17) .
C9 O5 K1 118.74(18) .
C10 O6 C11 112.0(2) .
C10 O6 K1 107.63(16) .
C11 O6 K1 112.80(17) .
C14 O7 Cu1 126.88(16) .
C18 O8 Cu1 121.30(13) .
C18 O8 K1 114.47(12) .
Cu1 O8 K1 124.02(7) .
C22 O9 Cu1 129.25(17) .
O1 C1 C2 108.2(2) .
O2 C2 C1 109.1(2) .
O2 C3 C4 108.8(3) .
O3 C4 C3 108.5(3) .
O3 C5 C6 109.0(3) .
O4 C6 C5 109.0(2) .
O4 C7 C8 109.5(2) .
O5 C8 C7 109.4(2) .
O5 C9 C10 109.8(3) .
O6 C10 C9 107.4(3) .
O6 C11 C12 107.8(2) .
O1 C12 C11 108.6(2) .
F3 C13 F1 106.9(2) .
F3 C13 F2 106.7(2) .
F1 C13 F2 106.8(2) .
F3 C13 C14 113.2(3) .
F1 C13 C14 110.0(2) .
F2 C13 C14 112.7(2) .
O7 C14 C16 114.5(2) .
O7 C14 C15 107.9(2) .
C16 C14 C15 108.6(2) .
O7 C14 C13 106.4(2) .
C16 C14 C13 109.6(2) .
C15 C14 C13 109.8(2) .
F5 C15 F4 106.8(2) .
F5 C15 F6 106.1(2) .
F4 C15 F6 106.1(3) .
F5 C15 C14 114.0(3) .
F4 C15 C14 113.9(3) .
F6 C15 C14 109.4(2) .
F7 C17 F8 106.7(3) .
F7 C17 F9 106.8(3) .
F8 C17 F9 106.3(3) .
F7 C17 C18 111.3(3) .
F8 C17 C18 111.7(2) .
F9 C17 C18 113.6(3) .
O8 C18 C19 108.0(3) .
O8 C18 C20 115.11(18) .
C19 C18 C20 108.3(3) .
O8 C18 C17 106.7(2) .
C19 C18 C17 110.4(2) .
C20 C18 C17 108.3(3) .
F10 C19 F11 107.0(3) .
F10 C19 F12 106.3(3) .
F11 C19 F12 107.5(3) .
F10 C19 C18 113.6(3) .
F11 C19 C18 112.3(3) .
F12 C19 C18 109.8(3) .
C18 C20 K1 157.64(16) 1_565
F13 C21 F15 106.7(3) .
F13 C21 F14 106.2(3) .
F15 C21 F14 106.9(3) .
F13 C21 C22 110.3(3) .
F15 C21 C22 113.0(3) .
F14 C21 C22 113.2(3) .
O9 C22 C24 115.6(2) .
O9 C22 C23 106.6(2) .
C24 C22 C23 108.1(2) .
O9 C22 C21 107.1(2) .
C24 C22 C21 110.0(3) .
C23 C22 C21 109.3(2) .
F17 C23 F16 106.5(2) .
F17 C23 F18 105.4(2) .
F16 C23 F18 105.4(3) .
F17 C23 C22 114.2(3) .
F16 C23 C22 114.2(2) .
F18 C23 C22 110.4(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O7 1.8283(18) .
Cu1 O9 1.8349(19) .
Cu1 O8 1.8576(15) .
K1 O5 2.8141(19) .
K1 O8 2.8456(16) .
K1 O4 2.860(2) .
K1 O3 2.864(2) .
K1 O1 2.872(2) .
K1 F11 2.891(2) .
K1 F8 2.8957(19) .
K1 O6 2.904(2) .
K1 O2 2.914(2) .
K1 C20 3.490(3) 1_545
F1 C13 1.340(4) .
F2 C13 1.346(3) .
F3 C13 1.329(4) .
F4 C15 1.338(4) .
F5 C15 1.325(4) .
F6 C15 1.352(4) .
F7 C17 1.319(4) .
F8 C17 1.343(3) .
F9 C17 1.345(4) .
F10 C19 1.332(4) .
F11 C19 1.337(4) .
F12 C19 1.339(5) .
F13 C21 1.335(4) .
F14 C21 1.349(4) .
F15 C21 1.341(4) .
F16 C23 1.342(4) .
F17 C23 1.331(3) .
F18 C23 1.345(4) .
O1 C12 1.419(4) .
O1 C1 1.425(3) .
O2 C3 1.404(4) .
O2 C2 1.425(4) .
O3 C4 1.414(4) .
O3 C5 1.426(4) .
O4 C6 1.413(4) .
O4 C7 1.435(4) .
O5 C8 1.422(4) .
O5 C9 1.427(4) .
O6 C10 1.419(3) .
O6 C11 1.429(4) .
O7 C14 1.381(3) .
O8 C18 1.379(3) .
O9 C22 1.377(3) .
C1 C2 1.478(5) .
C3 C4 1.504(5) .
C5 C6 1.499(5) .
C7 C8 1.483(5) .
C9 C10 1.489(5) .
C11 C12 1.496(4) .
C13 C14 1.540(4) .
C14 C16 1.524(4) .
C14 C15 1.538(4) .
C17 C18 1.541(4) .
C18 C19 1.530(5) .
C18 C20 1.532(3) .
C20 K1 3.490(3) 1_565
C21 C22 1.530(4) .
C22 C24 1.522(4) .
C22 C23 1.529(4) .
