#------------------------------------------------------------------------------
#$Date: 2020-06-05 13:45:29 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252778 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/41/7704122.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_7704122
loop_
_publ_author_name
'Navarro, Yolanda'
'Guedes, Guilherme P.'
'Cano, Joan'
'Ocón, Pilar'
'Iglesias, María José'
'Lloret, Francisco'
'López-Ortiz, Fernando'
_publ_section_title
;
 Synthesis, structural characterization and electrochemical and magnetic
 studies of M(hfac)₂ (M = CuII, CoII) and
 Nd(hfac)₃ complexes of 4-amino-TEMPO.
;
_journal_issue                   19
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6280
_journal_page_last               6294
_journal_paper_doi               10.1039/d0dt00541j
_journal_volume                  49
_journal_year                    2020
_chemical_formula_sum            'C19 H21 Cu F12 N2 O5'
_chemical_formula_weight         648.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-01-16 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.785(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.826(2)
_cell_length_b                   21.226(2)
_cell_length_c                   12.0638(12)
_cell_measurement_reflns_used    2793
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      17.11
_cell_measurement_theta_min      2.32
_cell_volume                     5255.3(9)
_computing_cell_refinement       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_collection       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_reduction        'Bruker Saint (Bruker AXS, 2007)'
_computing_molecular_graphics    'Mercury (Bruno, 2002)'
_computing_publication_material
'WinGX publication routines (Farrugia, 1999) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ-ω scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1146
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11963
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        23.253
_diffrn_reflns_theta_max         23.253
_diffrn_reflns_theta_min         1.380
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_description       Block
_exptl_crystal_F_000             2608
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.044
_refine_diff_density_max         1.094
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         3777
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0810
_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)+(0.1362P)²+15.9715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2203
_refine_ls_wR_factor_ref         0.2403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2837
_reflns_number_total             3777
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00541j2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7704121--7704125.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7704122
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.68471(3) 0.29006(3) 0.04840(6) 0.0370(4) Uani 1 1 d . . . . .
O2 O 0.7531(2) 0.23183(19) 0.1196(4) 0.0389(10) Uani 1 1 d . . . . .
O4 O 0.6296(2) 0.21882(18) -0.0123(4) 0.0457(12) Uani 1 1 d . . . . .
N2 N 0.7469(2) 0.3613(2) 0.0781(4) 0.0334(11) Uani 1 1 d . . . . .
H2A H 0.7860 0.3470 0.0699 0.040 Uiso 1 1 calc R U . . .
H2B H 0.7353 0.3899 0.0245 0.040 Uiso 1 1 calc R U . . .
O5 O 0.6146(2) 0.3496(2) -0.0027(5) 0.0618(15) Uani 1 1 d . . . . .
F1 F 0.8711(3) 0.2263(4) 0.2706(7) 0.147(3) Uani 1 1 d . . . . .
O1 O 0.7521(3) 0.5368(3) 0.4214(5) 0.0872(19) Uani 1 1 d . . . . .
F3 F 0.8314(4) 0.1559(4) 0.3633(5) 0.137(3) Uani 1 1 d . . . . .
C6 C 0.6905(3) 0.4204(3) 0.2076(7) 0.0562(19) Uani 1 1 d . . . . .
H6A H 0.6595 0.3860 0.2038 0.067 Uiso 1 1 calc R U . . .
H6B H 0.6745 0.4494 0.1471 0.067 Uiso 1 1 calc R U . . .
C1 C 0.8134(4) 0.4853(4) 0.3028(7) 0.063(2) Uani 1 1 d . . . . .
C5 C 0.7544(3) 0.3945(3) 0.1887(5) 0.0421(16) Uani 1 1 d . . . . .
H5 H 0.7703 0.3644 0.2488 0.051 Uiso 1 1 calc R U . . .
O3 O 0.6311(3) 0.2756(3) 0.1969(6) 0.0837(18) Uani 1 1 d . . . . .
F2 F 0.8389(4) 0.1421(4) 0.1941(6) 0.152(3) Uani 1 1 d . . . . .
N1 N 0.7503(3) 0.4972(3) 0.3400(5) 0.0570(16) Uani 1 1 d . . . . .
C2 C 0.8576(5) 0.4504(5) 0.3958(8) 0.109(4) Uani 1 1 d . . . . .
H2C H 0.8987 0.4424 0.3729 0.164 Uiso 1 1 calc R U . . .
H2D H 0.8642 0.4757 0.4628 0.164 Uiso 1 1 calc R U . . .
H2E H 0.8376 0.4112 0.4105 0.164 Uiso 1 1 calc R U . . .
C17 C 0.5298(3) 0.2746(3) -0.0517(6) 0.0513(18) Uani 1 1 d . . . . .
H17 H 0.4850 0.2700 -0.0734 0.062 Uiso 1 1 calc R U . . .
C16 C 0.5685(3) 0.2222(3) -0.0420(6) 0.0459(17) Uani 1 1 d . . . . .
C11 C 0.7597(4) 0.2157(3) 0.2224(6) 0.0445(17) Uani 1 1 d . . . . .
C3 C 0.8426(5) 0.5500(4) 0.2832(9) 0.092(3) Uani 1 1 d . . . . .
H3A H 0.8838 0.5444 0.2589 0.138 Uiso 1 1 calc R U . . .
H3B H 0.8135 0.5724 0.2265 0.138 Uiso 1 1 calc R U . . .
H3C H 0.8488 0.5737 0.3520 0.138 Uiso 1 1 calc R U . . .
C18 C 0.5559(3) 0.3350(3) -0.0297(6) 0.0520(18) Uani 1 1 d . . . . .
C12 C 0.7182(5) 0.2209(5) 0.2955(9) 0.094(3) Uani 1 1 d . U . . .
H12 H 0.7350 0.2074 0.3680 0.112 Uiso 1 1 calc R U . . .
C8 C 0.7004(9) 0.4045(6) 0.4174(10) 0.160(7) Uani 1 1 d . . . . .
H8A H 0.6640 0.3761 0.4061 0.240 Uiso 1 1 calc R U . . .
H8B H 0.7400 0.3811 0.4184 0.240 Uiso 1 1 calc R U . . .
H8C H 0.7021 0.4260 0.4878 0.240 Uiso 1 1 calc R U . . .
C7 C 0.6925(4) 0.4543(4) 0.3184(8) 0.076(3) Uani 1 1 d . . . . .
C10 C 0.8219(4) 0.1829(4) 0.2647(6) 0.062(2) Uani 1 1 d . . . . .
C4 C 0.8022(3) 0.4485(3) 0.1938(6) 0.0491(17) Uani 1 1 d . . . . .
H4A H 0.8437 0.4319 0.1811 0.059 Uiso 1 1 calc R U . . .
H4B H 0.7867 0.4774 0.1328 0.059 Uiso 1 1 calc R U . . .
C9 C 0.6315(5) 0.4933(6) 0.3155(12) 0.138(6) Uani 1 1 d . . . . .
H9A H 0.5940 0.4664 0.3017 0.206 Uiso 1 1 calc R U . . .
H9B H 0.6330 0.5143 0.3864 0.206 Uiso 1 1 calc R U . . .
H9C H 0.6288 0.5241 0.2566 0.206 Uiso 1 1 calc R U . . .
C19 C 0.5096(4) 0.3911(4) -0.0409(10) 0.079(3) Uani 1 1 d . . . . .
F9 F 0.4744(2) 0.1629(2) -0.1101(7) 0.127(3) Uani 1 1 d . . . . .
F8 F 0.5642(3) 0.1243(4) -0.1261(10) 0.196(5) Uani 1 1 d . . . . .
F7 F 0.5383(4) 0.1279(3) 0.0312(10) 0.167(4) Uani 1 1 d . . . . .
C15 C 0.5355(4) 0.1606(4) -0.0683(12) 0.091(3) Uani 1 1 d . . . . .
F6 F 0.5783(5) 0.1808(4) 0.3502(8) 0.172(4) Uani 1 1 d . . . . .
C13 C 0.6557(5) 0.2425(4) 0.2820(8) 0.074(2) Uani 1 1 d . U . . .
F4 F 0.6419(4) 0.2296(4) 0.4750(5) 0.124(2) Uani 1 1 d . . . . .
F5 F 0.5645(5) 0.2812(4) 0.3468(13) 0.216(6) Uani 1 1 d . . . . .
C14 C 0.6089(7) 0.2340(6) 0.3654(12) 0.111(4) Uani 1 1 d . . . . .
F10A F 0.4543(8) 0.3782(7) -0.0167(13) 0.098(2) Uani 0.486(6) 1 d . . P A 1
F11A F 0.5012(5) 0.4067(5) -0.1590(13) 0.098(2) Uani 0.486(6) 1 d . . P A 1
F12A F 0.5366(6) 0.4407(6) 0.0071(14) 0.098(2) Uani 0.486(6) 1 d . . P A 1
F10B F 0.4472(7) 0.3789(7) -0.0735(12) 0.098(2) Uani 0.514(6) 1 d . . P A 2
F11B F 0.5251(5) 0.4397(6) -0.0838(13) 0.098(2) Uani 0.514(6) 1 d . . P A 2
F12B F 0.5067(5) 0.4126(5) 0.0745(12) 0.098(2) Uani 0.514(6) 1 d . . P A 2
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'
Cu Cu 0.3201 1.2651 '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'
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
O5 Cu1 O4 91.24(19) . . ?
O5 Cu1 O2 172.6(2) . . ?
O4 Cu1 O2 90.76(18) . . ?
O5 Cu1 N2 89.67(19) . . ?
O4 Cu1 N2 167.7(2) . . ?
O2 Cu1 N2 89.89(18) . . ?
O5 Cu1 O3 84.0(2) . . ?
O4 Cu1 O3 81.7(2) . . ?
O2 Cu1 O3 89.3(2) . . ?
N2 Cu1 O3 110.6(2) . . ?
C11 O2 Cu1 123.0(4) . . ?
C16 O4 Cu1 124.0(4) . . ?
C5 N2 Cu1 119.2(4) . . ?
C18 O5 Cu1 124.7(4) . . ?
C5 C6 C7 114.7(6) . . ?
N1 C1 C4 109.7(6) . . ?
N1 C1 C2 108.5(8) . . ?
C4 C1 C2 112.1(6) . . ?
N1 C1 C3 106.8(6) . . ?
C4 C1 C3 109.5(7) . . ?
C2 C1 C3 110.1(8) . . ?
C6 C5 N2 110.5(5) . . ?
C6 C5 C4 108.2(5) . . ?
N2 C5 C4 111.2(5) . . ?
C13 O3 Cu1 121.4(6) . . ?
O1 N1 C1 115.4(6) . . ?
O1 N1 C7 116.7(6) . . ?
C1 N1 C7 124.9(5) . . ?
C16 C17 C18 121.5(6) . . ?
O4 C16 C17 128.5(6) . . ?
O4 C16 C15 114.6(6) . . ?
C17 C16 C15 116.9(6) . . ?
O2 C11 C12 130.2(8) . . ?
O2 C11 C10 113.9(6) . . ?
C12 C11 C10 115.9(7) . . ?
O5 C18 C17 127.5(6) . . ?
O5 C18 C19 113.9(6) . . ?
C17 C18 C19 118.6(7) . . ?
C11 C12 C13 131.2(10) . . ?
N1 C7 C6 110.2(6) . . ?
N1 C7 C9 108.5(7) . . ?
C6 C7 C9 110.0(8) . . ?
N1 C7 C8 107.4(9) . . ?
C6 C7 C8 109.5(7) . . ?
C9 C7 C8 111.3(10) . . ?
F3 C10 F2 106.8(7) . . ?
F3 C10 F1 104.6(7) . . ?
F2 C10 F1 101.4(8) . . ?
F3 C10 C11 120.4(7) . . ?
F2 C10 C11 113.9(6) . . ?
F1 C10 C11 107.6(7) . . ?
C1 C4 C5 115.4(6) . . ?
F10A C19 F12A 114.8(12) . . ?
F11B C19 F10B 110.9(10) . . ?
F10A C19 F11A 108.3(10) . . ?
F12A C19 F11A 103.1(10) . . ?
F11B C19 F12B 101.2(11) . . ?
F10B C19 F12B 98.4(10) . . ?
F11B C19 C18 119.3(8) . . ?
F10A C19 C18 113.4(10) . . ?
F12A C19 C18 112.3(8) . . ?
F10B C19 C18 116.8(10) . . ?
F11A C19 C18 103.7(9) . . ?
F12B C19 C18 106.6(8) . . ?
F8 C15 F9 109.7(9) . . ?
F8 C15 F7 102.8(9) . . ?
F9 C15 F7 104.6(9) . . ?
F8 C15 C16 114.4(9) . . ?
F9 C15 C16 116.2(7) . . ?
F7 C15 C16 107.9(9) . . ?
O3 C13 C12 121.7(9) . . ?
O3 C13 C14 112.4(10) . . ?
C12 C13 C14 125.8(11) . . ?
F6 C14 F5 108.5(12) . . ?
F6 C14 F4 103.3(10) . . ?
F5 C14 F4 115.0(12) . . ?
F6 C14 C13 111.3(10) . . ?
F5 C14 C13 107.3(10) . . ?
F4 C14 C13 111.5(11) . . ?
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 O5 1.950(4) . ?
Cu1 O4 1.964(4) . ?
Cu1 O2 1.970(4) . ?
Cu1 N2 1.983(5) . ?
Cu1 O3 2.287(7) . ?
O2 C11 1.272(8) . ?
O4 C16 1.263(8) . ?
N2 C5 1.494(7) . ?
O5 C18 1.248(8) . ?
F1 C10 1.371(10) . ?
O1 N1 1.288(7) . ?
F3 C10 1.305(9) . ?
C6 C5 1.493(9) . ?
C6 C7 1.512(10) . ?
C1 N1 1.481(10) . ?
C1 C4 1.513(10) . ?
C1 C2 1.516(11) . ?
C1 C3 1.537(11) . ?
C5 C4 1.513(9) . ?
O3 C13 1.277(11) . ?
F2 C10 1.305(9) . ?
N1 C7 1.496(10) . ?
C17 C16 1.367(9) . ?
C17 C18 1.401(10) . ?
C16 C15 1.486(11) . ?
C11 C12 1.339(12) . ?
C11 C10 1.483(10) . ?
C18 C19 1.524(10) . ?
C12 C13 1.364(13) . ?
C8 C7 1.583(15) . ?
C7 C9 1.513(13) . ?
C19 F11B 1.221(14) . ?
C19 F10A 1.265(18) . ?
C19 F12A 1.285(16) . ?
C19 F10B 1.319(17) . ?
C19 F11A 1.445(17) . ?
C19 F12B 1.476(16) . ?
F9 C15 1.287(9) . ?
F8 C15 1.255(12) . ?
F7 C15 1.379(14) . ?
F6 C14 1.294(13) . ?
C13 C14 1.527(13) . ?
F4 C14 1.386(15) . ?
F5 C14 1.354(15) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O4 0.89 2.44 3.293(6) 160.9 7_655
N2 H2B O1 0.89 2.06 2.887(7) 154.4 6_565
C6 H6A O5 0.97 2.62 3.136(9) 113.2 .
C6 H6A O3 0.97 2.41 3.307(9) 152.7 .
C4 H4A F8 0.97 2.44 3.402(9) 169.2 7_655
C4 H4B O1 0.97 2.55 3.289(9) 133.4 6_565
C9 H9B F11B 0.96 2.53 3.053(15) 114.2 6_566
C9 H9C F2 0.96 2.63 3.223(15) 119.9 4_655
