#------------------------------------------------------------------------------
#$Date: 2019-11-15 11:40:50 +0200 (Fri, 15 Nov 2019) $
#$Revision: 227875 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/51/7235130.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_7235130
loop_
_publ_author_name
'N. A. Artiukhova'
'G. V. Romanenko'
'A. S. Bogomyakov'
'I. Yu. Barskaya'
'S. L. Veber'
'M. V. Fedin'
'K. Yu. Maryunina'
'K. Inoue'
'V. I. Ovcharenko'
_publ_section_title
;
 Cu(ii) complex with nitronyl nitroxide whose paramagnetism is suppressed
 by temperature decrease and/or pressure increase
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              11157
_journal_page_last               11163
_journal_paper_doi               10.1039/C6TC03216H
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C26 H25 Cu F12 N4 O6'
_chemical_formula_weight         781.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 111.680(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.481(2)
_cell_length_b                   14.380(2)
_cell_length_c                   16.521(3)
_cell_measurement_reflns_used    2338
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      22.71
_cell_measurement_theta_min      2.45
_cell_volume                     2976.2(8)
_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-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_unetI/netI     0.1339
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15246
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.194
_diffrn_reflns_theta_min         1.676
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_description       bulk
_exptl_crystal_F_000             1576
_exptl_crystal_preparation       'Magnetic properties'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.016
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         5608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0892P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1989
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3007
_reflns_number_total             5608
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-4-11157.cif
_cod_data_source_block           87b-110
_cod_original_cell_volume        2976.1(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7235130
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.82819(6) 0.54458(5) 0.69781(5) 0.0232(2) Uani 1 1 d . . . . .
O1 O 0.7590(3) 0.5523(3) 0.5539(3) 0.0298(10) Uani 1 1 d . . . . .
C1 C 0.6243(5) 0.5619(5) 0.4135(4) 0.0331(17) Uani 1 1 d . . . . .
F1 F 0.649(3) 0.638(2) 0.3769(13) 0.053(7) Uani 0.5 1 d . . P A 1
F2 F 0.518(2) 0.5454(17) 0.3759(18) 0.034(5) Uani 0.5 1 d . . P A 1
F3 F 0.667(2) 0.487(2) 0.3925(13) 0.071(9) Uani 0.5 1 d . . P A 1
F1A F 0.672(3) 0.618(2) 0.3775(19) 0.079(12) Uani 0.5 1 d . . P A 2
F2A F 0.525(3) 0.5738(17) 0.374(2) 0.045(7) Uani 0.5 1 d . . P A 2
F3A F 0.655(3) 0.4803(18) 0.3959(19) 0.076(10) Uani 0.5 1 d . . P A 2
C2 C 0.6644(5) 0.5756(4) 0.5132(4) 0.0281(15) Uani 1 1 d . . . . .
C3 C 0.5920(5) 0.6161(4) 0.5456(4) 0.0285(15) Uani 1 1 d . . . . .
H3A H 0.5213 0.6282 0.5064 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6200(5) 0.6393(4) 0.6335(4) 0.0278(15) Uani 1 1 d . . . . .
C5 C 0.5389(5) 0.6898(4) 0.6612(4) 0.0321(16) Uani 1 1 d . . . . .
F4 F 0.5233(3) 0.6468(3) 0.7266(2) 0.0454(10) Uani 1 1 d . . . . .
F5 F 0.5730(3) 0.7765(3) 0.6885(3) 0.0467(11) Uani 1 1 d . . . . .
F6 F 0.4429(3) 0.6998(3) 0.5975(2) 0.0422(10) Uani 1 1 d . . . . .
O2 O 0.7073(3) 0.6249(3) 0.6958(3) 0.0297(11) Uani 1 1 d . . . . .
O3 O 0.9511(3) 0.4641(3) 0.7057(3) 0.0278(10) Uani 1 1 d . . . . .
C6 C 1.1262(5) 0.4089(5) 0.7458(4) 0.0323(16) Uani 1 1 d . . . . .
F8 F 1.2226(3) 0.4122(3) 0.8052(3) 0.0688(15) Uani 1 1 d . . . . .
F7 F 1.0997(4) 0.3189(3) 0.7336(3) 0.0627(13) Uani 1 1 d . . . . .
F9 F 1.1329(3) 0.4373(3) 0.6723(3) 0.0597(13) Uani 1 1 d . . . . .
C7 C 1.0417(5) 0.4637(4) 0.7676(4) 0.0262(15) Uani 1 1 d . . . . .
C8 C 1.0734(5) 0.5057(4) 0.8485(4) 0.0283(15) Uani 1 1 d . . . . .
H8A H 1.1462 0.5008 0.8861 0.034 Uiso 1 1 calc R U . . .
C9 C 1.0029(5) 0.5555(4) 0.8779(4) 0.0241(14) Uani 1 1 d . . . . .
C10 C 1.0555(6) 0.6109(5) 0.9630(5) 0.0404(18) Uani 1 1 d . . . . .
F10 F 1.0631(4) 0.6999(3) 0.9433(3) 0.0583(12) Uani 1 1 d . . . . .
F11 F 1.1525(3) 0.5818(3) 1.0124(2) 0.0520(12) Uani 1 1 d . . . . .
F12 F 0.9959(3) 0.6077(3) 1.0123(2) 0.0471(11) Uani 1 1 d . . . . .
O4 O 0.9053(3) 0.5628(3) 0.8439(3) 0.0264(10) Uani 1 1 d . . . . .
O1R O 0.5763(3) 0.1550(3) 0.7879(3) 0.0266(10) Uani 1 1 d . . . . .
N2R N 0.5808(4) 0.2199(3) 0.8446(3) 0.0237(12) Uani 1 1 d . . . . .
C3R C 0.5113(5) 0.2158(4) 0.8982(4) 0.0232(14) Uani 1 1 d . . . . .
C4R C 0.3943(5) 0.2243(4) 0.8351(4) 0.0286(15) Uani 1 1 d . . . . .
H4RA H 0.3846 0.1969 0.7777 0.034 Uiso 1 1 calc R U . . .
H4RB H 0.3716 0.2902 0.8268 0.034 Uiso 1 1 calc R U . . .
C5R C 0.3300(5) 0.1692(5) 0.8800(4) 0.0341(16) Uani 1 1 d . . . . .
H5RA H 0.2819 0.2114 0.8957 0.041 Uiso 1 1 calc R U . . .
H5RB H 0.2865 0.1203 0.8406 0.041 Uiso 1 1 calc R U . . .
C6R C 0.4122(5) 0.1256(4) 0.9619(4) 0.0285(15) Uani 1 1 d . . . . .
H6RA H 0.3898 0.0625 0.9720 0.034 Uiso 1 1 calc R U . . .
H6RB H 0.4224 0.1645 1.0138 0.034 Uiso 1 1 calc R U . . .
C7R C 0.5153(5) 0.1219(4) 0.9416(4) 0.0268(15) Uani 1 1 d . . . . .
H7RA H 0.5796 0.1160 0.9955 0.032 Uiso 1 1 calc R U . . .
H7RB H 0.5136 0.0700 0.9017 0.032 Uiso 1 1 calc R U . . .
C8R C 0.5555(5) 0.3011(4) 0.9590(4) 0.0238(14) Uani 1 1 d . . . . .
C9R C 0.4759(5) 0.3585(4) 0.9863(4) 0.0273(15) Uani 1 1 d . . . . .
H9RA H 0.4652 0.4208 0.9589 0.033 Uiso 1 1 calc R U . . .
H9RB H 0.4060 0.3266 0.9681 0.033 Uiso 1 1 calc R U . . .
C10A C 0.5247(5) 0.3670(5) 1.0849(4) 0.0364(17) Uani 1 1 d . . . . .
H10C H 0.5054 0.4271 1.1044 0.044 Uiso 1 1 calc R U . . .
H10D H 0.5005 0.3157 1.1132 0.044 Uiso 1 1 calc R U . . .
C11A C 0.6434(5) 0.3612(5) 1.1058(4) 0.0361(17) Uani 1 1 d . . . . .
H11C H 0.6824 0.3452 1.1678 0.043 Uiso 1 1 calc R U . . .
H11D H 0.6716 0.4205 1.0926 0.043 Uiso 1 1 calc R U . . .
C12R C 0.6515(5) 0.2837(4) 1.0462(4) 0.0283(15) Uani 1 1 d . . . . .
H12A H 0.6457 0.2221 1.0708 0.034 Uiso 1 1 calc R U . . .
H12B H 0.7201 0.2871 1.0373 0.034 Uiso 1 1 calc R U . . .
N13R N 0.5978(4) 0.3581(3) 0.9026(3) 0.0256(12) Uani 1 1 d . . . . .
O14R O 0.6205(3) 0.4446(3) 0.9158(3) 0.0304(11) Uani 1 1 d . . . . .
C15R C 0.6178(5) 0.3061(4) 0.8419(4) 0.0220(14) Uani 1 1 d . . . . .
C16R C 0.6649(4) 0.3402(4) 0.7829(4) 0.0243(14) Uani 1 1 d . . . . .
C17R C 0.7097(4) 0.4275(4) 0.7803(4) 0.0251(15) Uani 1 1 d . . . . .
H17A H 0.7146 0.4763 0.8204 0.030 Uiso 1 1 calc R U . . .
N18R N 0.7444(4) 0.4336(3) 0.7149(3) 0.0267(12) Uani 1 1 d . . . . .
N19R N 0.7235(4) 0.3480(3) 0.6750(3) 0.0241(12) Uani 1 1 d . . . . .
C20R C 0.7562(5) 0.3280(4) 0.6004(4) 0.0312(16) Uani 1 1 d . . . . .
H20A H 0.8303 0.3500 0.6144 0.037 Uiso 1 1 calc R U . . .
H20B H 0.7093 0.3628 0.5487 0.037 Uiso 1 1 calc R U . . .
C21R C 0.7501(5) 0.2260(4) 0.5792(4) 0.0321(16) Uani 1 1 d . . . . .
H21A H 0.7723 0.2159 0.5297 0.048 Uiso 1 1 calc R U . . .
H21B H 0.7974 0.1915 0.6298 0.048 Uiso 1 1 calc R U . . .
H21C H 0.6765 0.2043 0.5642 0.048 Uiso 1 1 calc R U . . .
C22R C 0.6751(4) 0.2912(4) 0.7125(4) 0.0231(14) Uani 1 1 d . . . . .
H22A H 0.6520 0.2294 0.6952 0.028 Uiso 1 1 calc R U . . .
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
O3 Cu1 O2 177.40(17) . .
O3 Cu1 O1R 88.26(17) . 2_656
O2 Cu1 O1R 91.67(17) . 2_656
O3 Cu1 N18R 91.48(18) . .
O2 Cu1 N18R 87.96(18) . .
O1R Cu1 N18R 166.28(18) 2_656 .
O3 Cu1 O1 96.30(15) . .
O2 Cu1 O1 86.29(16) . .
O1R Cu1 O1 94.85(15) 2_656 .
N18R Cu1 O1 98.81(18) . .
O3 Cu1 O4 87.37(15) . .
O2 Cu1 O4 90.09(15) . .
O1R Cu1 O4 76.12(15) 2_656 .
N18R Cu1 O4 90.16(18) . .
O1 Cu1 O4 170.18(15) . .
C2 O1 Cu1 122.2(4) . .
F2A C1 F1A 107(2) . .
F2A C1 F3A 111.9(19) . .
F1A C1 F3A 102(2) . .
F3 C1 F1 110(2) . .
F3 C1 F2 102.9(19) . .
F1 C1 F2 109.1(19) . .
F2A C1 C2 114.4(16) . .
F1A C1 C2 111.7(13) . .
F3 C1 C2 111.6(10) . .
F3A C1 C2 109.6(14) . .
F1 C1 C2 109.1(11) . .
F2 C1 C2 114.0(15) . .
O1 C2 C3 128.5(6) . .
O1 C2 C1 115.2(6) . .
C3 C2 C1 116.2(6) . .
O1 C2 Cu1 37.6(3) . .
C3 C2 Cu1 91.6(4) . .
C1 C2 Cu1 151.9(4) . .
C4 C3 C2 122.4(6) . .
O2 C4 C3 128.4(6) . .
O2 C4 C5 113.0(6) . .
C3 C4 C5 118.6(6) . .
O2 C4 Cu1 32.0(3) . .
C3 C4 Cu1 96.9(4) . .
C5 C4 Cu1 144.1(4) . .
F4 C5 F6 107.0(5) . .
F4 C5 F5 107.3(5) . .
F6 C5 F5 106.0(5) . .
F4 C5 C4 111.7(5) . .
F6 C5 C4 114.0(5) . .
F5 C5 C4 110.4(5) . .
C4 O2 Cu1 128.4(4) . .
C7 O3 Cu1 125.9(4) . .
F9 C6 F7 105.4(6) . .
F9 C6 F8 107.1(6) . .
F7 C6 F8 106.5(5) . .
F9 C6 C7 111.6(5) . .
F7 C6 C7 110.6(5) . .
F8 C6 C7 115.1(5) . .
O3 C7 C8 129.7(6) . .
O3 C7 C6 113.0(5) . .
C8 C7 C6 117.3(5) . .
O3 C7 Cu1 33.5(3) . .
C8 C7 Cu1 96.7(4) . .
C6 C7 Cu1 145.3(4) . .
C7 C8 C9 123.1(6) . .
O4 C9 C8 129.0(6) . .
O4 C9 C10 115.3(6) . .
C8 C9 C10 115.7(5) . .
O4 C9 Cu1 41.1(3) . .
C8 C9 Cu1 90.8(4) . .
C10 C9 Cu1 148.0(4) . .
F11 C10 F10 107.8(6) . .
F11 C10 F12 106.9(6) . .
F10 C10 F12 107.4(6) . .
F11 C10 C9 114.5(6) . .
F10 C10 C9 108.9(6) . .
F12 C10 C9 111.1(6) . .
C9 O4 Cu1 118.0(4) . .
N2R O1R Cu1 128.6(3) . 2_646
O1R N2R C15R 123.7(5) . .
O1R N2R C3R 121.2(5) . .
C15R N2R C3R 111.9(5) . .
O1R N2R Cu1 31.5(2) . 2_646
C15R N2R Cu1 125.5(4) . 2_646
C3R N2R Cu1 120.0(3) . 2_646
N2R C3R C7R 113.0(5) . .
N2R C3R C4R 107.5(5) . .
C7R C3R C4R 103.8(5) . .
N2R C3R C8R 100.1(4) . .
C7R C3R C8R 117.1(5) . .
C4R C3R C8R 115.2(5) . .
C3R C4R C5R 104.4(5) . .
C6R C5R C4R 106.4(5) . .
C5R C6R C7R 103.8(5) . .
C3R C7R C6R 101.2(5) . .
N13R C8R C9R 110.6(5) . .
N13R C8R C3R 99.9(4) . .
C9R C8R C3R 117.9(5) . .
N13R C8R C12R 106.5(5) . .
C9R C8R C12R 104.2(5) . .
C3R C8R C12R 117.3(5) . .
C10A C9R C8R 106.4(5) . .
C11A C10A C9R 104.1(5) . .
C10A C11A C12R 102.5(5) . .
C11A C12R C8R 104.3(5) . .
O14R N13R C15R 124.2(5) . .
O14R N13R C8R 123.1(5) . .
C15R N13R C8R 112.5(5) . .
N2R C15R N13R 107.9(5) . .
N2R C15R C16R 126.9(5) . .
N13R C15R C16R 125.1(5) . .
C17R C16R C22R 104.4(5) . .
C17R C16R C15R 129.1(6) . .
C22R C16R C15R 126.5(6) . .
N18R C17R C16R 111.6(6) . .
N18R C17R Cu1 35.0(3) . .
C16R C17R Cu1 146.2(5) . .
C17R N18R N19R 105.0(5) . .
C17R N18R Cu1 123.0(4) . .
N19R N18R Cu1 131.4(4) . .
C22R N19R N18R 112.0(5) . .
C22R N19R C20R 127.9(5) . .
N18R N19R C20R 120.1(5) . .
C22R N19R Cu1 140.9(4) . .
N18R N19R Cu1 29.3(2) . .
C20R N19R Cu1 90.9(3) . .
N19R C20R C21R 112.1(5) . .
N19R C22R C16R 106.9(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O3 1.985(4) .
Cu1 O2 1.988(4) .
Cu1 O1R 2.002(4) 2_656
Cu1 N18R 2.034(5) .
Cu1 O1 2.213(4) .
Cu1 O4 2.263(4) .
O1 C2 1.248(7) .
C1 F2A 1.27(3) .
C1 F1A 1.30(3) .
C1 F3 1.32(3) .
C1 F3A 1.31(3) .
C1 F1 1.35(3) .
C1 F2 1.35(3) .
C1 C2 1.545(9) .
C2 C3 1.402(8) .
C3 C4 1.398(8) .
C4 O2 1.261(7) .
C4 C5 1.518(9) .
C5 F4 1.327(7) .
C5 F6 1.341(7) .
C5 F5 1.347(7) .
O3 C7 1.271(7) .
C6 F9 1.316(7) .
C6 F7 1.338(7) .
C6 F8 1.307(7) .
C6 C7 1.533(9) .
C7 C8 1.383(8) .
C8 C9 1.412(8) .
C9 O4 1.229(7) .
C9 C10 1.542(9) .
C10 F11 1.328(8) .
C10 F10 1.334(8) .
C10 F12 1.340(7) .
O1R N2R 1.308(6) .
O1R Cu1 2.002(4) 2_646
N2R C15R 1.343(7) .
N2R C3R 1.509(7) .
N2R Cu1 2.997(5) 2_646
C3R C7R 1.520(8) .
C3R C4R 1.542(8) .
C3R C8R 1.558(8) .
C4R C5R 1.550(8) .
C5R C6R 1.531(8) .
C6R C7R 1.547(8) .
C8R N13R 1.503(7) .
C8R C9R 1.547(8) .
C8R C12R 1.561(8) .
C9R C10A 1.521(8) .
C10A C11A 1.509(9) .
C11A C12R 1.517(8) .
N13R O14R 1.280(6) .
N13R C15R 1.355(7) .
C15R C16R 1.433(8) .
C16R C17R 1.401(8) .
C16R C22R 1.408(8) .
C17R N18R 1.331(7) .
N18R N19R 1.375(6) .
N19R C22R 1.333(7) .
N19R C20R 1.482(7) .
C20R C21R 1.503(8) .
