#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/05/4310525.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_4310525
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                102.930(10)
_cell_angle_beta                 95.170(10)
_cell_angle_gamma                102.720(10)
_cell_formula_units_Z            2
_cell_length_a                   10.2310(10)
_cell_length_b                   11.104(2)
_cell_length_c                   13.751(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1469.2(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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       't\2t 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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0303
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5455
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_T_max  0.3648
_exptl_absorpt_correction_T_min  0.3022
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0177(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         5139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0705P)²+1.1369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1392
_reflns_number_gt                4294
_reflns_number_total             5139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic034964dsi20030813_090632_03.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               4310525
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 0.0561(2) Uani 1 2 d S . .
O1 O 0.3260(3) 0.5460(2) 0.49775(19) 0.0641(6) Uani 1 1 d . . .
C1 C 0.1688(5) 0.6661(5) 0.4818(5) 0.0951(15) Uani 1 1 d . . .
F1 F 0.1566(4) 0.7783(4) 0.4796(5) 0.193(2) Uani 1 1 d . . .
F2 F 0.1108(4) 0.5886(5) 0.3966(3) 0.1514(16) Uani 1 1 d . . .
F3 F 0.0952(4) 0.6297(5) 0.5483(4) 0.1590(16) Uani 1 1 d . . .
C2 C 0.3144(4) 0.6579(4) 0.5082(3) 0.0665(9) Uani 1 1 d . . .
C3 C 0.4131(5) 0.7689(4) 0.5415(4) 0.0786(12) Uani 1 1 d . . .
H3 H 0.391(5) 0.837(5) 0.551(4) 0.095(16) Uiso 1 1 d . . .
C4 C 0.5467(5) 0.7710(4) 0.5678(3) 0.0705(10) Uani 1 1 d . . .
C5 C 0.6453(6) 0.9002(5) 0.6114(5) 0.1023(17) Uani 1 1 d . . .
F4 F 0.6824(6) 0.9209(4) 0.7058(4) 0.203(3) Uani 1 1 d . . .
F5 F 0.7546(7) 0.9069(5) 0.5776(7) 0.278(5) Uani 1 1 d . . .
F6 F 0.6070(5) 0.9950(3) 0.5996(5) 0.204(3) Uani 1 1 d . . .
O2 O 0.5987(3) 0.6783(2) 0.56208(19) 0.0680(7) Uani 1 1 d . . .
Cu2 Cu 0.0000 0.0000 0.0000 0.0552(2) Uani 1 2 d S . .
O3 O 0.1503(2) -0.0113(2) -0.07563(18) 0.0529(5) Uani 1 1 d . . .
C6 C 0.3450(3) -0.0605(3) -0.1304(3) 0.0603(9) Uani 1 1 d . . .
F7 F 0.2893(3) -0.0949(4) -0.2239(2) 0.1283(13) Uani 1 1 d . . .
F8 F 0.4339(3) -0.1264(3) -0.1189(3) 0.1188(12) Uani 1 1 d . . .
F9 F 0.4148(3) 0.0576(2) -0.1153(2) 0.0957(8) Uani 1 1 d . . .
C7 C 0.2391(3) -0.0703(3) -0.0593(2) 0.0486(7) Uani 1 1 d . . .
C8 C 0.2497(3) -0.1382(3) 0.0119(3) 0.0549(8) Uani 1 1 d . . .
H8 H 0.317(4) -0.180(4) 0.014(3) 0.060(10) Uiso 1 1 d . . .
C9 C 0.1536(3) -0.1529(3) 0.0774(3) 0.0504(7) Uani 1 1 d . . .
C10 C 0.1717(4) -0.2344(4) 0.1504(3) 0.0686(10) Uani 1 1 d . . .
F10 F 0.2973(3) -0.2279(4) 0.1813(3) 0.1172(11) Uani 1 1 d . . .
F11 F 0.1124(3) -0.2066(3) 0.2302(2) 0.1135(10) Uani 1 1 d . . .
F12 F 0.1134(4) -0.3550(3) 0.1067(3) 0.1151(10) Uani 1 1 d . . .
O4 O 0.0505(2) -0.1104(2) 0.08204(18) 0.0554(5) Uani 1 1 d . . .
O01 O 0.4938(2) 0.5628(2) 0.34858(18) 0.0625(6) Uani 1 1 d . . .
N1 N 0.5476(3) 0.5308(2) 0.2686(2) 0.0514(6) Uani 1 1 d . . .
C01 C 0.6733(3) 0.6153(3) 0.2488(3) 0.0572(8) Uani 1 1 d . . .
C011 C 0.7786(5) 0.6605(5) 0.3427(4) 0.0760(11) Uani 1 1 d . . .
H111 H 0.744(5) 0.718(4) 0.393(4) 0.085(14) Uiso 1 1 d . . .
H112 H 0.800(5) 0.592(4) 0.364(3) 0.082(14) Uiso 1 1 d . . .
H113 H 0.858(5) 0.714(4) 0.324(3) 0.076(12) Uiso 1 1 d . . .
C012 C 0.6279(6) 0.7283(4) 0.2226(5) 0.0797(12) Uani 1 1 d . . .
H121 H 0.596(4) 0.767(4) 0.278(3) 0.076(13) Uiso 1 1 d . . .
H122 H 0.708(5) 0.792(5) 0.213(4) 0.094(15) Uiso 1 1 d . . .
H123 H 0.566(6) 0.705(5) 0.164(4) 0.107(18) Uiso 1 1 d . . .
C02 C 0.7087(3) 0.5249(3) 0.1576(3) 0.0553(8) Uani 1 1 d . . .
C021 C 0.7555(5) 0.5865(5) 0.0748(4) 0.0774(12) Uani 1 1 d . . .
H211 H 0.775(5) 0.523(5) 0.028(4) 0.097(17) Uiso 1 1 d . . .
H212 H 0.682(6) 0.618(5) 0.047(4) 0.108(17) Uiso 1 1 d . . .
H213 H 0.829(4) 0.660(4) 0.103(3) 0.069(11) Uiso 1 1 d . . .
C022 C 0.8051(5) 0.4487(5) 0.1869(5) 0.0759(11) Uani 1 1 d . . .
H221 H 0.815(4) 0.388(4) 0.133(4) 0.080(14) Uiso 1 1 d . . .
H222 H 0.893(5) 0.505(4) 0.217(3) 0.085(13) Uiso 1 1 d . . .
H223 H 0.775(5) 0.402(5) 0.234(4) 0.090(15) Uiso 1 1 d . . .
N2 N 0.5735(3) 0.4314(2) 0.1186(2) 0.0499(6) Uani 1 1 d . . .
O02 O 0.5495(2) 0.3521(2) 0.03253(18) 0.0606(6) Uani 1 1 d . . .
C03 C 0.4899(3) 0.4346(3) 0.1885(2) 0.0479(7) Uani 1 1 d . . .
C04 C 0.3574(3) 0.3508(3) 0.1793(2) 0.0470(7) Uani 1 1 d . . .
C05 C 0.2920(3) 0.2421(3) 0.1024(3) 0.0504(7) Uani 1 1 d . . .
H05 H 0.317(3) 0.210(3) 0.047(3) 0.046(9) Uiso 1 1 d . . .
N3 N 0.1711(3) 0.1891(3) 0.1210(2) 0.0539(6) Uani 1 1 d . . .
N4 N 0.1580(3) 0.2629(3) 0.2102(2) 0.0570(7) Uani 1 1 d . . .
C41 C 0.0395(5) 0.2318(7) 0.2588(4) 0.0861(15) Uani 1 1 d . . .
H411 H 0.058(6) 0.276(6) 0.318(5) 0.13(2) Uiso 1 1 d . . .
H412 H -0.024(6) 0.253(5) 0.217(5) 0.12(2) Uiso 1 1 d . . .
H413 H 0.014(5) 0.147(5) 0.249(4) 0.088(16) Uiso 1 1 d . . .
C06 C 0.2664(3) 0.3602(4) 0.2462(3) 0.0571(8) Uani 1 1 d . . .
H06 H 0.271(4) 0.417(4) 0.304(3) 0.062(10) 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 180.000(1) . 2_666 ?
O1 Cu1 O2 88.62(11) . 2_666 ?
O1 Cu1 O2 91.38(11) 2_666 2_666 ?
O1 Cu1 O2 91.38(11) . . ?
O1 Cu1 O2 88.62(11) 2_666 . ?
O2 Cu1 O2 180.0 2_666 . ?
O1 Cu1 O01 80.91(10) . . ?
O1 Cu1 O01 99.09(10) 2_666 . ?
O2 Cu1 O01 94.92(10) 2_666 . ?
O2 Cu1 O01 85.08(10) . . ?
O1 Cu1 O01 99.09(10) . 2_666 ?
O1 Cu1 O01 80.91(10) 2_666 2_666 ?
O2 Cu1 O01 85.08(10) 2_666 2_666 ?
O2 Cu1 O01 94.92(10) . 2_666 ?
O01 Cu1 O01 180.000(1) . 2_666 ?
C2 O1 Cu1 123.6(3) . . ?
F1 C1 F2 108.2(6) . . ?
F1 C1 F3 106.9(5) . . ?
F2 C1 F3 104.8(5) . . ?
F1 C1 C2 114.5(5) . . ?
F2 C1 C2 112.0(4) . . ?
F3 C1 C2 109.8(5) . . ?
O1 C2 C3 128.3(4) . . ?
O1 C2 C1 113.4(4) . . ?
C3 C2 C1 118.3(4) . . ?
C2 C3 C4 122.4(4) . . ?
O2 C4 C3 128.0(4) . . ?
O2 C4 C5 114.5(4) . . ?
C3 C4 C5 117.6(4) . . ?
F6 C5 F5 106.1(7) . . ?
F6 C5 F4 105.9(6) . . ?
F5 C5 F4 102.3(7) . . ?
F6 C5 C4 117.0(5) . . ?
F5 C5 C4 112.1(5) . . ?
F4 C5 C4 112.3(5) . . ?
C4 O2 Cu1 124.0(3) . . ?
O3 Cu2 O3 180.00(12) 2 . ?
O3 Cu2 O4 92.35(9) 2 2 ?
O3 Cu2 O4 87.65(9) . 2 ?
O3 Cu2 O4 87.65(9) 2 . ?
O3 Cu2 O4 92.35(9) . . ?
O4 Cu2 O4 180.00(16) 2 . ?
O3 Cu2 N3 95.82(9) 2 . ?
O3 Cu2 N3 84.18(9) . . ?
O4 Cu2 N3 91.29(9) 2 . ?
O4 Cu2 N3 88.71(9) . . ?
C7 O3 Cu2 124.8(2) . . ?
F7 C6 F8 108.6(4) . . ?
F7 C6 F9 105.8(4) . . ?
F8 C6 F9 105.7(3) . . ?
F7 C6 C7 111.6(3) . . ?
F8 C6 C7 113.8(3) . . ?
F9 C6 C7 110.8(3) . . ?
O3 C7 C8 128.3(3) . . ?
O3 C7 C6 112.5(3) . . ?
C8 C7 C6 119.2(3) . . ?
C7 C8 C9 121.6(3) . . ?
O4 C9 C8 128.2(3) . . ?
O4 C9 C10 114.5(3) . . ?
C8 C9 C10 117.3(3) . . ?
F10 C10 F11 107.8(4) . . ?
F10 C10 F12 107.0(4) . . ?
F11 C10 F12 105.2(4) . . ?
F10 C10 C9 113.9(3) . . ?
F11 C10 C9 112.6(3) . . ?
F12 C10 C9 109.8(3) . . ?
C9 O4 Cu2 124.6(2) . . ?
N1 O01 Cu1 132.1(2) . . ?
O01 N1 C03 125.3(3) . . ?
O01 N1 C01 121.5(3) . . ?
C03 N1 C01 112.2(3) . . ?
N1 C01 C011 109.9(3) . . ?
N1 C01 C012 105.2(3) . . ?
C011 C01 C012 110.5(4) . . ?
N1 C01 C02 100.7(2) . . ?
C011 C01 C02 115.9(3) . . ?
C012 C01 C02 113.6(4) . . ?
N2 C02 C021 109.1(3) . . ?
N2 C02 C022 106.4(3) . . ?
C021 C02 C022 110.9(4) . . ?
N2 C02 C01 100.9(2) . . ?
C021 C02 C01 115.1(3) . . ?
C022 C02 C01 113.6(3) . . ?
O02 N2 C03 125.6(3) . . ?
O02 N2 C02 122.3(3) . . ?
C03 N2 C02 111.8(3) . . ?
N1 C03 N2 109.0(3) . . ?
N1 C03 C04 124.6(3) . . ?
N2 C03 C04 126.4(3) . . ?
C06 C04 C05 104.1(3) . . ?
C06 C04 C03 126.9(3) . . ?
C05 C04 C03 129.0(3) . . ?
N3 C05 C04 111.5(3) . . ?
C05 N3 N4 104.9(3) . . ?
C05 N3 Cu2 124.9(2) . . ?
N4 N3 Cu2 130.01(19) . . ?
C06 N4 N3 112.0(3) . . ?
C06 N4 C41 126.5(3) . . ?
N3 N4 C41 121.5(3) . . ?
N4 C06 C04 107.6(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 1.957(3) . ?
Cu1 O1 1.957(3) 2_666 ?
Cu1 O2 1.969(2) 2_666 ?
Cu1 O2 1.969(2) . ?
Cu1 O01 2.339(3) . ?
Cu1 O01 2.339(3) 2_666 ?
O1 C2 1.251(4) . ?
C1 F1 1.286(6) . ?
C1 F2 1.289(7) . ?
C1 F3 1.312(7) . ?
C1 C2 1.528(7) . ?
C2 C3 1.365(6) . ?
C3 C4 1.377(6) . ?
C4 O2 1.249(5) . ?
C4 C5 1.518(6) . ?
C5 F6 1.239(7) . ?
C5 F5 1.242(8) . ?
C5 F4 1.273(7) . ?
Cu2 O3 1.943(2) 2 ?
Cu2 O3 1.943(2) . ?
Cu2 O4 1.959(2) 2 ?
Cu2 O4 1.959(2) . ?
Cu2 N3 2.557(3) . ?
O3 C7 1.264(4) . ?
C6 F7 1.295(5) . ?
C6 F8 1.306(4) . ?
C6 F9 1.308(4) . ?
C6 C7 1.525(5) . ?
C7 C8 1.373(5) . ?
C8 C9 1.399(5) . ?
C9 O4 1.247(4) . ?
C9 C10 1.520(5) . ?
C10 F10 1.297(4) . ?
C10 F11 1.310(5) . ?
C10 F12 1.317(5) . ?
O01 N1 1.288(4) . ?
N1 C03 1.335(4) . ?
N1 C01 1.501(4) . ?
C01 C011 1.517(5) . ?
C01 C012 1.532(5) . ?
C01 C02 1.546(5) . ?
C02 N2 1.505(4) . ?
C02 C021 1.515(5) . ?
C02 C022 1.516(5) . ?
N2 O02 1.273(3) . ?
N2 C03 1.343(4) . ?
C03 C04 1.443(4) . ?
C04 C06 1.370(5) . ?
C04 C05 1.403(4) . ?
C05 N3 1.321(4) . ?
N3 N4 1.350(4) . ?
N4 C06 1.332(4) . ?
N4 C41 1.450(5) . ?
