#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/05/4310527.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_4310527
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                102.56(2)
_cell_angle_beta                 96.54(5)
_cell_angle_gamma                102.59(6)
_cell_formula_units_Z            2
_cell_length_a                   10.190(12)
_cell_length_b                   10.848(6)
_cell_length_c                   13.395(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1390(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.760
_diffrn_measured_fraction_theta_max 0.760
_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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2970
_diffrn_reflns_theta_full        22.48
_diffrn_reflns_theta_max         22.48
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.910
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_refine_diff_density_max         0.714
_refine_diff_density_min         -1.209
_refine_diff_density_rms         0.163
_refine_ls_extinction_coef       0.000(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   2.316
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.316
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0814
_refine_ls_shift/su_max          5.147
_refine_ls_shift/su_mean         0.028
_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          0.1981
_refine_ls_wR_factor_ref         0.2208
_reflns_number_gt                2293
_reflns_number_total             2754
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic034964dsi20030813_090632_05.cif
_cod_data_source_block           aa1
_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_cell_volume        1390.1(19)
_cod_database_code               4310527
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 0.0273(7) Uani 1 2 d S . .
O1 O 0.3310(10) 0.5508(6) 0.5078(5) 0.053(3) Uani 1 1 d . . .
C1 C 0.1692(17) 0.6690(10) 0.4915(8) 0.048(4) Uani 1 1 d . . .
F1 F 0.1473(9) 0.7875(6) 0.4935(6) 0.080(3) Uani 1 1 d . . .
F2 F 0.1113(8) 0.5955(6) 0.3948(4) 0.058(2) Uani 1 1 d . . .
F3 F 0.0941(8) 0.6198(6) 0.5559(4) 0.054(2) Uani 1 1 d . . .
C2 C 0.3109(15) 0.6662(9) 0.5170(7) 0.039(4) Uani 1 1 d . . .
C3 C 0.4187(16) 0.7832(9) 0.5532(7) 0.038(4) Uani 1 1 d . . .
H3 H 0.3948 0.8622 0.5594 0.22(11) Uiso 1 1 calc R . .
C4 C 0.5511(15) 0.7881(10) 0.5788(7) 0.033(3) Uani 1 1 d . . .
C5 C 0.6470(18) 0.9212(12) 0.6235(9) 0.058(4) Uani 1 1 d . . .
F4 F 0.6881(12) 0.9411(8) 0.7210(6) 0.124(4) Uani 1 1 d . . .
F5 F 0.7504(17) 0.9347(11) 0.5811(14) 0.224(10) Uani 1 1 d . . .
F6 F 0.5958(10) 1.0200(7) 0.6134(7) 0.109(4) Uani 1 1 d . . .
O2 O 0.6077(8) 0.6964(7) 0.5744(5) 0.039(2) Uani 1 1 d . . .
Cu2 Cu 0.0000 0.0000 0.0000 0.0284(7) Uani 1 2 d S . .
O3 O 0.1502(7) -0.0117(5) -0.0749(4) 0.0252(18) Uani 1 1 d . . .
C6 C 0.3418(12) -0.0630(8) -0.1308(7) 0.033(3) Uani 1 1 d . . .
F7 F 0.2863(7) -0.0876(6) -0.2292(4) 0.055(2) Uani 1 1 d . . .
F8 F 0.4281(8) -0.1405(6) -0.1252(5) 0.055(2) Uani 1 1 d . . .
F9 F 0.4237(7) 0.0590(5) -0.1071(4) 0.0445(18) Uani 1 1 d . . .
C7 C 0.2369(10) -0.0735(7) -0.0608(6) 0.016(2) Uani 1 1 d . . .
C8 C 0.2505(13) -0.1487(8) 0.0115(7) 0.035(3) Uani 1 1 d . . .
H8 H 0.3228 -0.1879 0.0159 0.00(2) Uiso 1 1 calc R . .
C9 C 0.1521(13) -0.1633(8) 0.0770(7) 0.027(3) Uani 1 1 d . . .
C10 C 0.1658(15) -0.2537(9) 0.1486(8) 0.035(3) Uani 1 1 d . . .
F10 F 0.2934(9) -0.2521(6) 0.1783(5) 0.056(2) Uani 1 1 d . . .
F11 F 0.1131(8) -0.2231(6) 0.2337(4) 0.057(2) Uani 1 1 d . . .
F12 F 0.1028(8) -0.3766(5) 0.1000(5) 0.059(2) Uani 1 1 d . . .
O4 O 0.0484(8) -0.1186(5) 0.0822(4) 0.028(2) Uani 1 1 d . . .
O01 O 0.4928(8) 0.5711(6) 0.3602(5) 0.042(2) Uani 1 1 d . . .
N1 N 0.5499(10) 0.5392(7) 0.2796(6) 0.038(3) Uani 1 1 d . . .
C01 C 0.6722(11) 0.6248(8) 0.2614(8) 0.031(3) Uani 1 1 d . . .
C011 C 0.7843(14) 0.6733(10) 0.3584(8) 0.045(3) Uani 1 1 d . . .
H111 H 0.7436 0.6684 0.4191 0.33(18) Uiso 1 1 calc R . .
H112 H 0.8313 0.7620 0.3639 0.6(4) Uiso 1 1 calc R . .
H113 H 0.8479 0.6196 0.3527 0.6(3) Uiso 1 1 calc R . .
C012 C 0.6308(17) 0.7426(9) 0.2316(10) 0.053(4) Uani 1 1 d . . .
H121 H 0.5400 0.7424 0.2446 0.13(8) Uiso 1 1 calc R . .
H122 H 0.6335 0.7365 0.1593 0.8(6) Uiso 1 1 calc R . .
H123 H 0.6931 0.8220 0.2724 0.16(8) Uiso 1 1 calc R . .
C02 C 0.7095(12) 0.5335(8) 0.1668(7) 0.033(3) Uani 1 1 d . . .
C021 C 0.7593(13) 0.5967(10) 0.0841(8) 0.046(3) Uani 1 1 d . . .
H211 H 0.7740 0.5317 0.0282 0.03(3) Uiso 1 1 calc R . .
H212 H 0.8434 0.6616 0.1128 0.03(3) Uiso 1 1 calc R . .
H213 H 0.6923 0.6372 0.0583 0.03(3) Uiso 1 1 calc R . .
C022 C 0.8016(13) 0.4518(9) 0.2000(8) 0.044(3) Uani 1 1 d . . .
H221 H 0.8027 0.3829 0.1416 0.04(3) Uiso 1 1 calc R . .
H222 H 0.7680 0.4151 0.2540 0.03(2) Uiso 1 1 calc R . .
H223 H 0.8925 0.5058 0.2253 0.02(2) Uiso 1 1 calc R . .
N2 N 0.5747(9) 0.4396(6) 0.1257(6) 0.029(2) Uani 1 1 d . . .
O02 O 0.5463(9) 0.3600(5) 0.0345(5) 0.044(2) Uani 1 1 d . . .
C03 C 0.4832(12) 0.4403(8) 0.1942(7) 0.029(3) Uani 1 1 d . . .
C04 C 0.3564(11) 0.3561(7) 0.1841(6) 0.021(3) Uani 1 1 d . . .
C05 C 0.2883(13) 0.2409(8) 0.1037(7) 0.029(3) Uani 1 1 d . . .
H05 H 0.371(11) 0.205(10) 0.052(8) 0.05(3) Uiso 1 1 d . . .
N3 N 0.1682(11) 0.1864(7) 0.1223(5) 0.031(3) Uani 1 1 d . . .
N4 N 0.1530(9) 0.2653(7) 0.2131(5) 0.025(2) Uani 1 1 d . . .
C41 C 0.0398(14) 0.2304(10) 0.2611(7) 0.046(4) Uani 1 1 d . . .
H411 H 0.0688 0.2505 0.3348 0.11(5) Uiso 1 1 calc R . .
H412 H -0.0011 0.1386 0.2355 0.26(13) Uiso 1 1 calc R . .
H413 H -0.0256 0.2782 0.2459 0.11(6) Uiso 1 1 calc R . .
C06 C 0.2652(11) 0.3661(8) 0.2513(7) 0.025(3) Uani 1 1 d . . .
H06 H 0.279(9) 0.449(8) 0.311(6) 0.03(2) 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(2) . 2_666 ?
O1 Cu1 O2 91.0(3) . 2_666 ?
O1 Cu1 O2 89.0(3) 2_666 2_666 ?
O1 Cu1 O2 89.0(3) . . ?
O1 Cu1 O2 91.0(3) 2_666 . ?
O2 Cu1 O2 180.0(3) 2_666 . ?
O1 Cu1 O01 83.2(3) . . ?
O1 Cu1 O01 96.8(3) 2_666 . ?
O2 Cu1 O01 96.0(2) 2_666 . ?
O2 Cu1 O01 84.0(2) . . ?
O1 Cu1 O01 96.8(3) . 2_666 ?
O1 Cu1 O01 83.2(3) 2_666 2_666 ?
O2 Cu1 O01 84.0(2) 2_666 2_666 ?
O2 Cu1 O01 96.0(2) . 2_666 ?
O01 Cu1 O01 180.000(2) . 2_666 ?
C2 O1 Cu1 128.0(9) . . ?
F3 C1 F1 106.7(10) . . ?
F3 C1 F2 106.0(11) . . ?
F1 C1 F2 104.8(9) . . ?
F3 C1 C2 111.0(9) . . ?
F1 C1 C2 115.7(11) . . ?
F2 C1 C2 112.0(10) . . ?
O1 C2 C3 123.0(13) . . ?
O1 C2 C1 114.9(10) . . ?
C3 C2 C1 122.1(10) . . ?
C4 C3 C2 125.3(11) . . ?
O2 C4 C3 129.0(10) . . ?
O2 C4 C5 113.9(13) . . ?
C3 C4 C5 117.1(11) . . ?
F5 C5 F4 107.4(16) . . ?
F5 C5 F6 105.0(14) . . ?
F4 C5 F6 105.6(11) . . ?
F5 C5 C4 111.4(11) . . ?
F4 C5 C4 111.6(11) . . ?
F6 C5 C4 115.2(13) . . ?
C4 O2 Cu1 121.5(8) . . ?
O3 Cu2 O3 180.0(3) . 2 ?
O3 Cu2 O4 92.0(3) . . ?
O3 Cu2 O4 88.0(3) 2 . ?
O3 Cu2 O4 88.0(3) . 2 ?
O3 Cu2 O4 92.0(3) 2 2 ?
O4 Cu2 O4 180.0(5) . 2 ?
O3 Cu2 N3 95.9(3) . 2 ?
O3 Cu2 N3 84.1(3) 2 2 ?
O4 Cu2 N3 89.7(2) . 2 ?
O4 Cu2 N3 90.3(2) 2 2 ?
O3 Cu2 N3 84.1(3) . . ?
O3 Cu2 N3 95.9(3) 2 . ?
O4 Cu2 N3 90.3(2) . . ?
O4 Cu2 N3 89.7(2) 2 . ?
N3 Cu2 N3 180.0(4) 2 . ?
C7 O3 Cu2 126.3(6) . . ?
F7 C6 F9 105.9(7) . . ?
F7 C6 F8 107.2(8) . . ?
F9 C6 F8 104.5(9) . . ?
F7 C6 C7 112.4(9) . . ?
F9 C6 C7 111.0(7) . . ?
F8 C6 C7 115.1(8) . . ?
O3 C7 C8 129.2(10) . . ?
O3 C7 C6 113.8(8) . . ?
C8 C7 C6 117.0(9) . . ?
C9 C8 C7 118.6(10) . . ?
O4 C9 C8 129.9(9) . . ?
O4 C9 C10 113.5(10) . . ?
C8 C9 C10 116.5(10) . . ?
F10 C10 F11 107.1(9) . . ?
F10 C10 F12 106.5(9) . . ?
F11 C10 F12 107.5(10) . . ?
F10 C10 C9 112.2(10) . . ?
F11 C10 C9 112.7(9) . . ?
F12 C10 C9 110.6(8) . . ?
C9 O4 Cu2 123.9(6) . . ?
N1 O01 Cu1 128.6(6) . . ?
O01 N1 C03 122.1(10) . . ?
O01 N1 C01 122.1(7) . . ?
C03 N1 C01 113.9(9) . . ?
N1 C01 C012 107.8(10) . . ?
N1 C01 C011 111.7(9) . . ?
C012 C01 C011 109.6(8) . . ?
N1 C01 C02 101.3(7) . . ?
C012 C01 C02 111.7(9) . . ?
C011 C01 C02 114.4(10) . . ?
N2 C02 C021 110.2(8) . . ?
N2 C02 C022 104.6(7) . . ?
C021 C02 C022 111.9(10) . . ?
N2 C02 C01 99.9(8) . . ?
C021 C02 C01 116.2(8) . . ?
C022 C02 C01 112.6(8) . . ?
O02 N2 C03 122.4(8) . . ?
O02 N2 C02 123.0(9) . . ?
C03 N2 C02 114.6(7) . . ?
N1 C03 N2 104.5(9) . . ?
N1 C03 C04 126.6(10) . . ?
N2 C03 C04 128.7(8) . . ?
C06 C04 C03 126.4(8) . . ?
C06 C04 C05 103.8(9) . . ?
C03 C04 C05 129.7(10) . . ?
N3 C05 C04 111.5(9) . . ?
C05 N3 N4 105.4(8) . . ?
C05 N3 Cu2 124.5(6) . . ?
N4 N3 Cu2 129.5(7) . . ?
C06 N4 N3 111.1(9) . . ?
C06 N4 C41 127.6(8) . . ?
N3 N4 C41 120.9(8) . . ?
N4 C06 C04 108.1(8) . . ?
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 1.926(9) . ?
Cu1 O1 1.926(9) 2_666 ?
Cu1 O2 2.132(8) 2_666 ?
Cu1 O2 2.132(8) . ?
Cu1 O01 2.174(7) . ?
Cu1 O01 2.174(7) 2_666 ?
O1 C2 1.293(12) . ?
C1 F3 1.336(14) . ?
C1 F1 1.347(12) . ?
C1 F2 1.354(12) . ?
C1 C2 1.454(17) . ?
C2 C3 1.435(16) . ?
C3 C4 1.340(16) . ?
C4 O2 1.249(13) . ?
C4 C5 1.508(17) . ?
C5 F5 1.249(17) . ?
C5 F4 1.281(13) . ?
C5 F6 1.315(15) . ?
Cu2 O3 1.936(7) . ?
Cu2 O3 1.936(7) 2 ?
Cu2 O4 1.970(6) . ?
Cu2 O4 1.970(6) 2 ?
Cu2 N3 2.473(8) 2 ?
Cu2 N3 2.473(8) . ?
O3 C7 1.242(10) . ?
C6 F7 1.319(10) . ?
C6 F9 1.350(11) . ?
C6 F8 1.349(11) . ?
C6 C7 1.502(14) . ?
C7 C8 1.408(13) . ?
C8 C9 1.412(15) . ?
C9 O4 1.257(12) . ?
C9 C10 1.530(13) . ?
C10 F10 1.310(13) . ?
C10 F11 1.324(12) . ?
C10 F12 1.329(12) . ?
O01 N1 1.300(11) . ?
N1 C03 1.376(12) . ?
N1 C01 1.463(14) . ?
C01 C012 1.545(13) . ?
C01 C011 1.540(14) . ?
C01 C02 1.568(13) . ?
C02 N2 1.484(14) . ?
C02 C021 1.504(14) . ?
C02 C022 1.518(14) . ?
N2 O02 1.294(9) . ?
N2 C03 1.380(13) . ?
C03 C04 1.384(15) . ?
C04 C06 1.370(14) . ?
C04 C05 1.439(12) . ?
C05 N3 1.314(14) . ?
N3 N4 1.373(10) . ?
N4 C06 1.357(12) . ?
N4 C41 1.404(15) . ?
