#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/05/4310526.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_4310526
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 H19 Cu F12 N4 O6'
_chemical_formula_weight         714.94
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.000(10)
_cell_angle_beta                 96.030(10)
_cell_angle_gamma                102.630(10)
_cell_formula_units_Z            2
_cell_length_a                   10.2020(10)
_cell_length_b                   10.885(2)
_cell_length_c                   13.610(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1418.0(4)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '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  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4949
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  0.5874
_exptl_absorpt_correction_T_min  0.4611
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0086(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         4688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0380
_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)+(0.0566P)²+1.2538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                3985
_reflns_number_total             4688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic034964dsi20030813_090632_04.cif
_cod_data_source_block           aa
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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_database_code               4310526
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.5000 0.02794(16) Uani 1 2 d S . .
O1 O 0.3262(2) 0.54738(19) 0.50078(16) 0.0345(5) Uani 1 1 d . . .
C1 C 0.1668(4) 0.6689(3) 0.4873(3) 0.0491(9) Uani 1 1 d . . .
F1 F 0.1537(3) 0.7876(2) 0.4906(3) 0.0966(10) Uani 1 1 d . . .
F2 F 0.1099(2) 0.5939(3) 0.39526(19) 0.0697(7) Uani 1 1 d . . .
F3 F 0.0938(2) 0.6248(3) 0.5532(2) 0.0745(7) Uani 1 1 d . . .
C2 C 0.3150(3) 0.6625(3) 0.5134(2) 0.0355(7) Uani 1 1 d . . .
C3 C 0.4137(4) 0.7773(3) 0.5483(3) 0.0416(8) Uani 1 1 d . . .
H3 H 0.392(4) 0.851(4) 0.556(3) 0.049(10) Uiso 1 1 d . . .
C4 C 0.5495(3) 0.7785(3) 0.5750(2) 0.0377(7) Uani 1 1 d . . .
C5 C 0.6509(4) 0.9102(3) 0.6199(3) 0.0525(9) Uani 1 1 d . . .
F4 F 0.6831(4) 0.9313(3) 0.7184(2) 0.1190(14) Uani 1 1 d . . .
F5 F 0.7639(4) 0.9161(3) 0.5873(4) 0.177(2) Uani 1 1 d . . .
F6 F 0.6083(3) 1.0085(2) 0.6055(3) 0.1174(14) Uani 1 1 d . . .
O2 O 0.6015(2) 0.6836(2) 0.56748(16) 0.0380(5) Uani 1 1 d . . .
Cu2 Cu 0.0000 0.0000 0.0000 0.02641(15) Uani 1 2 d S . .
O3 O 0.15037(18) -0.01223(18) -0.07572(15) 0.0272(4) Uani 1 1 d . . .
C6 C 0.3455(3) -0.0628(3) -0.1299(2) 0.0315(7) Uani 1 1 d . . .
F7 F 0.2873(2) -0.0929(3) -0.22650(16) 0.0624(6) Uani 1 1 d . . .
F8 F 0.4302(2) -0.1375(2) -0.1218(2) 0.0648(7) Uani 1 1 d . . .
F9 F 0.42041(19) 0.05771(18) -0.10925(17) 0.0505(5) Uani 1 1 d . . .
C7 C 0.2382(2) -0.0740(2) -0.0592(2) 0.0259(6) Uani 1 1 d . . .
C8 C 0.2486(3) -0.1447(3) 0.0123(2) 0.0312(7) Uani 1 1 d . . .
H8 H 0.308(3) -0.187(3) 0.015(2) 0.028(8) Uiso 1 1 d . . .
C9 C 0.1529(3) -0.1593(3) 0.0776(2) 0.0273(6) Uani 1 1 d . . .
C10 C 0.1690(3) -0.2461(3) 0.1499(3) 0.0370(7) Uani 1 1 d . . .
F10 F 0.2980(2) -0.2417(2) 0.18051(19) 0.0613(6) Uani 1 1 d . . .
F11 F 0.1135(2) -0.2151(2) 0.23269(17) 0.0570(6) Uani 1 1 d . . .
F12 F 0.1067(2) -0.36940(19) 0.10327(18) 0.0588(6) Uani 1 1 d . . .
O4 O 0.05048(18) -0.11448(18) 0.08289(15) 0.0281(4) Uani 1 1 d . . .
O01 O 0.4939(2) 0.57159(19) 0.35377(16) 0.0345(5) Uani 1 1 d . . .
N1 N 0.5485(2) 0.5384(2) 0.27340(19) 0.0292(5) Uani 1 1 d . . .
C01 C 0.6750(3) 0.6248(3) 0.2547(2) 0.0313(6) Uani 1 1 d . . .
C011 C 0.7815(3) 0.6704(4) 0.3511(3) 0.0410(8) Uani 1 1 d . . .
H111 H 0.750(4) 0.726(3) 0.404(3) 0.042(9) Uiso 1 1 d . . .
H112 H 0.808(4) 0.603(4) 0.375(3) 0.046(10) Uiso 1 1 d . . .
H113 H 0.860(4) 0.720(3) 0.333(3) 0.039(9) Uiso 1 1 d . . .
C012 C 0.6306(4) 0.7406(3) 0.2278(4) 0.0446(9) Uani 1 1 d . . .
H121 H 0.597(4) 0.779(3) 0.283(3) 0.043(10) Uiso 1 1 d . . .
H122 H 0.714(4) 0.800(4) 0.214(3) 0.052(10) Uiso 1 1 d . . .
H123 H 0.565(4) 0.719(3) 0.167(3) 0.041(9) Uiso 1 1 d . . .
C02 C 0.7104(3) 0.5317(3) 0.1628(2) 0.0295(6) Uani 1 1 d . . .
C021 C 0.7594(4) 0.5948(4) 0.0805(3) 0.0427(8) Uani 1 1 d . . .
H211 H 0.782(4) 0.529(4) 0.034(3) 0.061(12) Uiso 1 1 d . . .
H212 H 0.692(4) 0.635(3) 0.051(3) 0.042(9) Uiso 1 1 d . . .
H213 H 0.830(4) 0.660(4) 0.108(3) 0.054(11) Uiso 1 1 d . . .
C022 C 0.8052(3) 0.4517(3) 0.1944(3) 0.0409(8) Uani 1 1 d . . .
H221 H 0.813(4) 0.384(4) 0.138(3) 0.046(10) Uiso 1 1 d . . .
H222 H 0.889(4) 0.506(4) 0.222(3) 0.046(10) Uiso 1 1 d . . .
H223 H 0.773(4) 0.406(4) 0.249(3) 0.047(10) Uiso 1 1 d . . .
N2 N 0.5735(2) 0.4374(2) 0.12123(18) 0.0269(5) Uani 1 1 d . . .
O02 O 0.54853(19) 0.35748(19) 0.03283(15) 0.0315(5) Uani 1 1 d . . .
C03 C 0.4894(3) 0.4408(3) 0.1907(2) 0.0261(6) Uani 1 1 d . . .
C04 C 0.3559(3) 0.3554(2) 0.1799(2) 0.0252(6) Uani 1 1 d . . .
C05 C 0.2906(3) 0.2425(3) 0.1025(2) 0.0269(6) Uani 1 1 d . . .
H05 H 0.319(3) 0.205(3) 0.044(2) 0.021(7) Uiso 1 1 d . . .
N3 N 0.1692(2) 0.1883(2) 0.12108(18) 0.0275(5) Uani 1 1 d . . .
N4 N 0.1565(2) 0.2659(2) 0.21082(18) 0.0297(5) Uani 1 1 d . . .
C41 C 0.0384(3) 0.2326(4) 0.2599(3) 0.0450(9) Uani 1 1 d . . .
H411 H 0.059(4) 0.277(4) 0.326(3) 0.054(11) Uiso 1 1 d . . .
H412 H -0.030(5) 0.252(4) 0.225(3) 0.058(12) Uiso 1 1 d . . .
H413 H 0.015(4) 0.143(4) 0.252(3) 0.051(11) Uiso 1 1 d . . .
C06 C 0.2648(3) 0.3656(3) 0.2475(2) 0.0296(6) Uani 1 1 d . . .
H06 H 0.267(3) 0.422(3) 0.306(3) 0.029(8) 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'
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 Cu1 O1 180.0 2_666 . ?
O1 Cu1 O2 88.85(9) 2_666 . ?
O1 Cu1 O2 91.15(9) . . ?
O1 Cu1 O2 91.15(9) 2_666 2_666 ?
O1 Cu1 O2 88.85(9) . 2_666 ?
O2 Cu1 O2 180.0 . 2_666 ?
O1 Cu1 O01 98.45(8) 2_666 . ?
O1 Cu1 O01 81.55(8) . . ?
O2 Cu1 O01 84.07(8) . . ?
O2 Cu1 O01 95.93(8) 2_666 . ?
O1 Cu1 O01 81.55(8) 2_666 2_666 ?
O1 Cu1 O01 98.45(8) . 2_666 ?
O2 Cu1 O01 95.93(8) . 2_666 ?
O2 Cu1 O01 84.07(8) 2_666 2_666 ?
O01 Cu1 O01 180.0 . 2_666 ?
C2 O1 Cu1 123.6(2) . . ?
F1 C1 F2 107.9(3) . . ?
F1 C1 F3 107.4(3) . . ?
F2 C1 F3 106.8(3) . . ?
F1 C1 C2 113.6(3) . . ?
F2 C1 C2 111.2(3) . . ?
F3 C1 C2 109.7(3) . . ?
O1 C2 C3 129.3(3) . . ?
O1 C2 C1 112.4(3) . . ?
C3 C2 C1 118.3(3) . . ?
C2 C3 C4 121.3(3) . . ?
O2 C4 C3 128.2(3) . . ?
O2 C4 C5 114.0(3) . . ?
C3 C4 C5 117.8(3) . . ?
F5 C5 F6 107.7(4) . . ?
F5 C5 F4 104.3(4) . . ?
F6 C5 F4 106.0(4) . . ?
F5 C5 C4 112.6(3) . . ?
F6 C5 C4 114.9(3) . . ?
F4 C5 C4 110.7(3) . . ?
C4 O2 Cu1 123.8(2) . . ?
O3 Cu2 O3 180.00(10) . 2 ?
O3 Cu2 O4 87.69(8) . 2 ?
O3 Cu2 O4 92.31(8) 2 2 ?
O3 Cu2 O4 92.31(8) . . ?
O3 Cu2 O4 87.69(8) 2 . ?
O4 Cu2 O4 180.00(14) 2 . ?
O3 Cu2 N3 84.27(8) . . ?
O3 Cu2 N3 95.73(8) 2 . ?
O4 Cu2 N3 90.95(8) 2 . ?
O4 Cu2 N3 89.05(8) . . ?
C7 O3 Cu2 124.56(19) . . ?
F9 C6 F7 106.6(3) . . ?
F9 C6 F8 106.8(2) . . ?
F7 C6 F8 108.0(3) . . ?
F9 C6 C7 110.7(2) . . ?
F7 C6 C7 111.0(2) . . ?
F8 C6 C7 113.5(2) . . ?
O3 C7 C8 128.8(3) . . ?
O3 C7 C6 112.2(2) . . ?
C8 C7 C6 119.0(2) . . ?
C7 C8 C9 121.3(3) . . ?
O4 C9 C8 128.5(3) . . ?
O4 C9 C10 114.2(2) . . ?
C8 C9 C10 117.2(2) . . ?
F11 C10 F10 107.4(3) . . ?
F11 C10 F12 106.6(3) . . ?
F10 C10 F12 107.3(3) . . ?
F11 C10 C9 112.4(2) . . ?
F10 C10 C9 112.8(2) . . ?
F12 C10 C9 110.0(3) . . ?
C9 O4 Cu2 124.38(19) . . ?
N1 O01 Cu1 129.78(17) . . ?
O01 N1 C03 125.3(2) . . ?
O01 N1 C01 121.6(2) . . ?
C03 N1 C01 112.0(2) . . ?
N1 C01 C011 109.7(3) . . ?
N1 C01 C012 105.6(2) . . ?
C011 C01 C012 110.7(3) . . ?
N1 C01 C02 100.6(2) . . ?
C011 C01 C02 115.5(3) . . ?
C012 C01 C02 113.8(3) . . ?
N2 C02 C021 109.3(2) . . ?
N2 C02 C022 106.2(2) . . ?
C021 C02 C022 111.4(3) . . ?
N2 C02 C01 100.7(2) . . ?
C021 C02 C01 114.9(3) . . ?
C022 C02 C01 113.4(3) . . ?
O02 N2 C03 125.7(2) . . ?
O02 N2 C02 122.1(2) . . ?
C03 N2 C02 112.0(2) . . ?
N1 C03 N2 109.0(2) . . ?
N1 C03 C04 124.5(3) . . ?
N2 C03 C04 126.5(2) . . ?
C06 C04 C05 104.2(2) . . ?
C06 C04 C03 126.5(2) . . ?
C05 C04 C03 129.2(3) . . ?
N3 C05 C04 111.3(3) . . ?
C05 N3 N4 104.8(2) . . ?
C05 N3 Cu2 124.65(19) . . ?
N4 N3 Cu2 130.18(16) . . ?
C06 N4 N3 112.2(2) . . ?
C06 N4 C41 126.7(3) . . ?
N3 N4 C41 120.9(2) . . ?
N4 C06 C04 107.4(3) . . ?
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
Cu1 O1 1.953(2) 2_666 ?
Cu1 O1 1.953(2) . ?
Cu1 O2 1.995(2) . ?
Cu1 O2 1.995(2) 2_666 ?
Cu1 O01 2.295(2) . ?
Cu1 O01 2.295(2) 2_666 ?
O1 C2 1.257(4) . ?
C1 F1 1.319(4) . ?
C1 F2 1.324(4) . ?
C1 F3 1.328(4) . ?
C1 C2 1.537(4) . ?
C2 C3 1.372(5) . ?
C3 C4 1.391(5) . ?
C4 O2 1.250(4) . ?
C4 C5 1.524(5) . ?
C5 F5 1.272(5) . ?
C5 F6 1.285(5) . ?
C5 F4 1.301(5) . ?
Cu2 O3 1.9475(19) . ?
Cu2 O3 1.9475(19) 2 ?
Cu2 O4 1.9702(19) 2 ?
Cu2 O4 1.9702(19) . ?
Cu2 N3 2.496(2) . ?
O3 C7 1.263(3) . ?
C6 F9 1.317(3) . ?
C6 F7 1.321(4) . ?
C6 F8 1.322(3) . ?
C6 C7 1.534(4) . ?
C7 C8 1.379(4) . ?
C8 C9 1.396(4) . ?
C9 O4 1.248(3) . ?
C9 C10 1.529(4) . ?
C10 F11 1.323(4) . ?
C10 F10 1.325(3) . ?
C10 F12 1.329(4) . ?
O01 N1 1.294(3) . ?
N1 C03 1.341(4) . ?
N1 C01 1.503(4) . ?
C01 C011 1.524(4) . ?
C01 C012 1.532(4) . ?
C01 C02 1.552(4) . ?
C02 N2 1.507(3) . ?
C02 C021 1.512(5) . ?
C02 C022 1.525(4) . ?
N2 O02 1.279(3) . ?
N2 C03 1.342(4) . ?
C03 C04 1.443(4) . ?
C04 C06 1.379(4) . ?
C04 C05 1.406(4) . ?
C05 N3 1.326(4) . ?
N3 N4 1.356(3) . ?
N4 C06 1.328(4) . ?
N4 C41 1.454(4) . ?
