#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/05/4310531.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_4310531
loop_
_publ_author_name
'Sergei Fokin'
'Victor Ovcharenko'
'Galina Romanenko'
'Vladimir Ikorskii'
_publ_section_title
;
 Problem of a Wide Variety of Products in the Cu(hfac)2-Nitroxide System
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              969
_journal_page_last               977
_journal_paper_doi               10.1021/ic034964d
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C21.5 H20 Cl Cu F12 N4 O6'
_chemical_formula_weight         757.41
_space_group_IT_number           167
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3 2"c'
_symmetry_space_group_name_H-M   'R -3 c :H'
_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                120.00
_cell_formula_units_Z            36
_cell_length_a                   22.581(3)
_cell_length_b                   22.581(3)
_cell_length_c                   64.185(13)
_cell_measurement_temperature    293(2)
_cell_volume                     28343(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.1094
_diffrn_reflns_av_sigmaI/netI    0.3942
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       69
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4147
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.890
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             13644
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.000000(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.621
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         4107
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.622
_refine_ls_R_factor_all          0.2569
_refine_ls_R_factor_gt           0.0845
_refine_ls_shift/su_max          2.683
_refine_ls_shift/su_mean         0.157
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1353P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2479
_reflns_number_gt                886
_reflns_number_total             4107
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic034964dsi20030813_090632_09.cif
_cod_data_source_block           qqsp
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_original_formula_sum        'C21.50 H20 Cl Cu F12 N4 O6'
_cod_database_code               4310531
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.41488(3) 0.12953(3) 0.002668(13) 0.0765(3) Uani 1 1 d . . .
O1 O 0.42917(15) 0.08780(15) 0.02499(5) 0.0746(14) Uani 1 1 d . . .
C1 C 0.4709(3) 0.0692(3) 0.05555(11) 0.124(3) Uani 1 1 d . . .
F1 F 0.50005(17) 0.03664(16) 0.04681(8) 0.191(2) Uani 1 1 d . . .
F2 F 0.4138(2) 0.02315(18) 0.06341(8) 0.206(2) Uani 1 1 d . . .
F3 F 0.51018(17) 0.09684(15) 0.07234(7) 0.1678(18) Uani 1 1 d . . .
C2 C 0.46201(19) 0.11290(19) 0.03997(9) 0.0629(18) Uani 1 1 d . . .
C3 C 0.5006(2) 0.1842(2) 0.04555(9) 0.086(2) Uani 1 1 d . . .
H3A H 0.5173(12) 0.1932(12) 0.0600(5) 0.013(9) Uiso 1 1 d . . .
C4 C 0.5004(2) 0.2324(2) 0.03196(8) 0.071(2) Uani 1 1 d . . .
C5 C 0.5316(3) 0.3067(3) 0.04175(15) 0.276(4) Uani 1 1 d . . .
F4 F 0.50367(19) 0.33353(16) 0.03845(10) 0.311(3) Uani 1 1 d . . .
F5 F 0.57372(19) 0.32169(16) 0.05526(7) 0.176(2) Uani 1 1 d . . .
F6 F 0.5828(3) 0.3432(2) 0.02399(13) 0.311(5) Uani 1 1 d . . .
O2 O 0.47229(13) 0.22159(14) 0.01520(6) 0.0737(14) Uani 1 1 d . . .
O3 O 0.39433(12) 0.17018(14) -0.02018(6) 0.0704(14) Uani 1 1 d . . .
C6 C 0.4001(3) 0.2278(3) -0.04972(12) 0.136(4) Uani 1 1 d . . .
F7 F 0.43652(16) 0.25732(18) -0.06638(7) 0.178(2) Uani 1 1 d . . .
F8 F 0.39222(15) 0.27636(15) -0.04056(7) 0.1465(17) Uani 1 1 d . . .
F9 F 0.34113(15) 0.18259(16) -0.05711(7) 0.1571(18) Uani 1 1 d . . .
C7 C 0.42926(19) 0.1963(2) -0.03442(9) 0.070(2) Uani 1 1 d . . .
C8 C 0.4875(3) 0.2002(2) -0.04170(9) 0.090(3) Uani 1 1 d . . .
H8A H 0.5102(11) 0.2242(11) -0.0481(4) 0.000(8) Uiso 1 1 d . . .
C9 C 0.5232(2) 0.1728(2) -0.02990(8) 0.067(2) Uani 1 1 d . . .
C10 C 0.5898(3) 0.1846(3) -0.03915(11) 0.133(3) Uani 1 1 d . . .
F10 F 0.63322(17) 0.1913(3) -0.02406(8) 0.224(3) Uani 1 1 d . . .
F11 F 0.62193(17) 0.23117(19) -0.05165(8) 0.184(2) Uani 1 1 d . . .
F12 F 0.5843(2) 0.1298(2) -0.04624(10) 0.261(3) Uani 1 1 d . . .
O4 O 0.50513(13) 0.14160(15) -0.01393(6) 0.0856(15) Uani 1 1 d . . .
O01 O 0.33609(13) 0.14631(14) 0.02464(7) 0.1120(18) Uani 1 1 d . . .
N1 N 0.27622(17) 0.13000(16) 0.03087(7) 0.0794(18) Uani 1 1 d . . .
C01 C 0.2286(2) 0.0698(2) 0.04591(9) 0.071(2) Uani 1 1 d . . .
C011 C 0.2616(2) 0.0910(3) 0.06541(10) 0.119(3) Uani 1 1 d . . .
H01A H 0.3045 0.0917 0.0656 0.18(3) Uiso 1 1 d R . .
H01B H 0.2692 0.1358 0.0685 0.33(5) Uiso 1 1 d R . .
H01C H 0.2317 0.0592 0.0757 0.120(19) Uiso 1 1 d R . .
C012 C 0.2352(3) 0.0097(2) 0.03909(12) 0.147(4) Uani 1 1 d . . .
H01D H 0.2802 0.0172 0.0420 0.30(4) Uiso 1 1 d R . .
H01E H 0.2019 -0.0303 0.0464 0.064(13) Uiso 1 1 d R . .
H01F H 0.2266 0.0032 0.0244 0.19(3) Uiso 1 1 d R . .
C02 C 0.1614(2) 0.0668(2) 0.04084(9) 0.085(2) Uani 1 1 d . . .
C021 C 0.1212(3) 0.0226(3) 0.02295(10) 0.144(3) Uani 1 1 d . . .
H02A H 0.0788 0.0225 0.0219 0.119(19) Uiso 1 1 d R . .
H02B H 0.1475 0.0414 0.0105 0.58(10) Uiso 1 1 d R . .
H02C H 0.1121 -0.0235 0.0248 0.063(13) Uiso 1 1 d R . .
C022 C 0.1212(2) 0.0488(2) 0.05997(10) 0.106(3) Uani 1 1 d . . .
H02D H 0.0784 0.0465 0.0570 0.16(2) Uiso 1 1 d R . .
H02E H 0.1128 0.0050 0.0648 0.14(2) Uiso 1 1 d R . .
H02F H 0.1450 0.0825 0.0706 0.22(3) Uiso 1 1 d R . .
N2 N 0.18409(17) 0.14071(17) 0.03679(9) 0.105(2) Uani 1 1 d . . .
O02 O 0.14397(14) 0.16385(16) 0.03573(9) 0.156(2) Uani 1 1 d . . .
C03 C 0.2481(2) 0.1719(2) 0.02790(10) 0.081(2) Uani 1 1 d . . .
C04 C 0.28316(19) 0.2387(2) 0.02030(9) 0.078(2) Uani 1 1 d . . .
C05 C 0.2579(2) 0.2845(2) 0.01713(10) 0.085(2) Uani 1 1 d . . .
H05A H 0.2229(15) 0.2776(15) 0.0258(5) 0.050(12) Uiso 1 1 d . . .
N3 N 0.30639(16) 0.34365(16) 0.01013(8) 0.092(2) Uani 1 1 d . . .
N4 N 0.36278(16) 0.33751(17) 0.00648(9) 0.098(2) Uani 1 1 d . . .
C041 C 0.4284(2) 0.3930(2) -0.00157(10) 0.108(3) Uani 1 1 d . . .
H04A H 0.4225 0.4304 -0.0060 0.14(2) Uiso 1 1 d R . .
H04B H 0.4605 0.4077 0.0097 0.082(15) Uiso 1 1 d R . .
H04C H 0.4452 0.3781 -0.0130 0.28(4) Uiso 1 1 d R . .
C06 C 0.3506(2) 0.2773(2) 0.01406(11) 0.118(3) Uani 1 1 d . . .
H06A H 0.3829 0.2633 0.0150 0.000(8) Uiso 1 1 calc R . .
Cl Cl 0.62013(19) -0.0149(2) 0.07032(9) 0.440(4) Uani 1 1 d D . .
C1A C 0.6667 -0.0440(4) 0.0833 0.346(7) Uani 1 2 d SD . .
H1AB H 0.7050(19) -0.053(2) 0.0721(7) 0.129(18) Uiso 1 1 d . . .
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'
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'
F F 0.0171 0.0103 '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'
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
_geom_angle_publ_flag
O1 Cu O3 176.57(12) . . ?
O1 Cu O2 91.78(14) . . ?
O3 Cu O2 89.79(14) . . ?
O1 Cu N3 92.34(16) . 20 ?
O3 Cu N3 85.72(15) . 20 ?
O2 Cu N3 171.47(13) . 20 ?
O1 Cu O4 93.00(15) . . ?
O3 Cu O4 90.07(14) . . ?
O2 Cu O4 89.26(12) . . ?
N3 Cu O4 97.98(13) 20 . ?
O1 Cu O01 87.56(15) . . ?
O3 Cu O01 89.88(14) . . ?
O2 Cu O01 75.47(11) . . ?
N3 Cu O01 97.25(12) 20 . ?
O4 Cu O01 164.73(10) . . ?
C2 O1 Cu 128.7(3) . . ?
F2 C1 F1 107.0(5) . . ?
F2 C1 F3 102.9(5) . . ?
F1 C1 F3 101.7(5) . . ?
F2 C1 C2 112.7(5) . . ?
F1 C1 C2 110.6(5) . . ?
F3 C1 C2 120.6(5) . . ?
O1 C2 C3 128.8(5) . . ?
O1 C2 C1 119.5(4) . . ?
C3 C2 C1 111.6(5) . . ?
O1 C2 Cu 31.7(2) . . ?
C3 C2 Cu 97.1(3) . . ?
C1 C2 Cu 151.0(3) . . ?
C4 C3 C2 118.7(5) . . ?
C4 C3 Cu 62.0(3) . . ?
C2 C3 Cu 56.6(3) . . ?
O2 C4 C3 127.2(4) . . ?
O2 C4 C5 118.3(5) . . ?
C3 C4 C5 113.8(5) . . ?
O2 C4 Cu 34.8(2) . . ?
C3 C4 Cu 92.4(3) . . ?
C5 C4 Cu 151.7(4) . . ?
F4 C5 F5 125.3(8) . . ?
F4 C5 F6 92.7(7) . . ?
F5 C5 F6 96.1(5) . . ?
F4 C5 C4 115.8(6) . . ?
F5 C5 C4 116.9(6) . . ?
F6 C5 C4 95.2(6) . . ?
C4 O2 Cu 124.9(3) . . ?
C7 O3 Cu 125.8(3) . . ?
F9 C6 F7 103.8(6) . . ?
F9 C6 F8 107.6(5) . . ?
F7 C6 F8 104.5(5) . . ?
F9 C6 C7 112.1(5) . . ?
F7 C6 C7 116.8(5) . . ?
F8 C6 C7 111.3(6) . . ?
O3 C7 C8 134.2(6) . . ?
O3 C7 C6 113.5(5) . . ?
C8 C7 C6 112.0(5) . . ?
O3 C7 Cu 34.3(3) . . ?
C8 C7 Cu 100.3(4) . . ?
C6 C7 Cu 147.7(4) . . ?
C7 C8 C9 121.3(5) . . ?
O4 C9 C8 126.8(5) . . ?
O4 C9 C10 117.4(6) . . ?
C8 C9 C10 115.8(5) . . ?
O4 C9 Cu 39.0(3) . . ?
C8 C9 Cu 88.0(3) . . ?
C10 C9 Cu 156.0(4) . . ?
F11 C10 F12 109.2(7) . . ?
F11 C10 F10 106.9(5) . . ?
F12 C10 F10 94.5(7) . . ?
F11 C10 C9 121.2(7) . . ?
F12 C10 C9 111.5(5) . . ?
F10 C10 C9 110.2(6) . . ?
C9 O4 Cu 120.9(4) . . ?
N1 O01 Cu 152.3(3) . . ?
O01 N1 C03 122.6(4) . . ?
O01 N1 C01 127.6(4) . . ?
C03 N1 C01 109.0(4) . . ?
C011 C01 C012 106.8(5) . . ?
C011 C01 C02 123.4(5) . . ?
C012 C01 C02 116.5(4) . . ?
C011 C01 N1 103.6(3) . . ?
C012 C01 N1 105.6(4) . . ?
C02 C01 N1 98.2(4) . . ?
C022 C02 C021 112.0(4) . . ?
C022 C02 N2 106.0(5) . . ?
C021 C02 N2 111.5(5) . . ?
C022 C02 C01 107.5(5) . . ?
C021 C02 C01 116.8(5) . . ?
N2 C02 C01 102.1(3) . . ?
O02 N2 C03 123.9(4) . . ?
O02 N2 C02 123.7(3) . . ?
C03 N2 C02 109.1(4) . . ?
N2 C03 N1 108.4(4) . . ?
N2 C03 C04 125.5(5) . . ?
N1 C03 C04 125.4(4) . . ?
C06 C04 C03 129.3(5) . . ?
C06 C04 C05 102.4(4) . . ?
C03 C04 C05 128.3(4) . . ?
N3 C05 C04 110.9(4) . . ?
N3 C05 Cu 36.0(3) . 21 ?
C04 C05 Cu 145.1(3) . 21 ?
C05 N3 N4 107.5(4) . . ?
C05 N3 Cu 122.0(3) . 21 ?
N4 N3 Cu 126.8(3) . 21 ?
C06 N4 N3 108.2(4) . . ?
C06 N4 C041 126.9(4) . . ?
N3 N4 C041 124.3(4) . . ?
C06 N4 Cu 139.4(3) . 21 ?
N3 N4 Cu 32.4(2) . 21 ?
C041 N4 Cu 93.7(3) . 21 ?
N4 C06 C04 110.3(5) . . ?
Cl C1A Cl 92.5(5) . 18_654 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu O1 1.830(4) . ?
Cu O3 1.906(4) . ?
Cu O2 1.988(3) . ?
Cu N3 2.062(4) 20 ?
Cu O4 2.193(3) . ?
Cu O01 2.444(4) . ?
O1 C2 1.173(6) . ?
C1 F2 1.288(6) . ?
C1 F1 1.330(8) . ?
C1 F3 1.336(7) . ?
C1 C2 1.488(9) . ?
C2 C3 1.440(6) . ?
C3 C4 1.396(8) . ?
C4 O2 1.211(6) . ?
C4 C5 1.589(8) . ?
C5 F4 1.092(9) . ?
C5 F5 1.204(9) . ?
C5 F6 1.537(11) . ?
O3 C7 1.158(6) . ?
C6 F9 1.297(6) . ?
C6 F7 1.309(8) . ?
C6 F8 1.332(8) . ?
C6 C7 1.541(9) . ?
C7 C8 1.357(8) . ?
C8 C9 1.452(9) . ?
C9 O4 1.194(6) . ?
C9 C10 1.510(9) . ?
C10 F11 1.230(7) . ?
C10 F12 1.266(9) . ?
C10 F10 1.332(9) . ?
O01 N1 1.275(5) . ?
N1 C03 1.390(7) . ?
N1 C01 1.573(6) . ?
C01 C011 1.413(8) . ?
C01 C012 1.503(8) . ?
C01 C02 1.522(7) . ?
C02 C022 1.459(8) . ?
C02 C021 1.495(8) . ?
C02 N2 1.502(6) . ?
N2 O02 1.254(6) . ?
N2 C03 1.376(6) . ?
C03 C04 1.395(6) . ?
C04 C06 1.383(6) . ?
C04 C05 1.423(8) . ?
C05 N3 1.312(5) . ?
C05 Cu 2.974(5) 21 ?
N3 N4 1.368(6) . ?
N3 Cu 2.062(4) 21 ?
N4 C06 1.337(7) . ?
N4 C041 1.474(5) . ?
N4 Cu 3.084(4) 21 ?
Cl C1A 1.710(7) . ?
C1A Cl 1.710(7) 18_654 ?
