#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:35:09 +0200 (mar 06 de oct de 2020) $
#$Revision: 257507 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/53/7705390.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_7705390
loop_
_publ_author_name
'Kunert, R.'
'Philouze, C.'
'Berthiol, F.'
'Jarjayes, O.'
'Storr, T.'
'Thomas, F.'
_publ_section_title
;
 Distorted copper(ii) radicals with sterically hindered salens: electronic
 structure and aerobic oxidation of alcohols.
;
_journal_issue                   37
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12990
_journal_page_last               13002
_journal_paper_doi               10.1039/d0dt02524k
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C32 H46 Cu N2 O4'
_chemical_formula_sum            'C32 H46 Cu N2 O4'
_chemical_formula_weight         586.25
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2020-07-07 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   29.373(4)
_cell_length_b                   29.373(4)
_cell_length_c                   20.654(4)
_cell_measurement_reflns_used    30288
_cell_measurement_temperature    200
_cell_measurement_theta_max      24.999
_cell_measurement_theta_min      2.337
_cell_volume                     15432(4)
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'κ-geometry 4 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaAPEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30288
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.337
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.204758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.6119 before and 0.0955 after correction.
The Ratio of minimum to maximum transmission is 0.2048.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_description       needle
_exptl_crystal_F_000             5634
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.668
_refine_diff_density_min         -1.192
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0684
_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)+(0.1481P)²+15.6062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1861
_refine_ls_wR_factor_ref         0.2187
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2269
_reflns_number_total             3013
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt02524k2.cif
_cod_data_source_block           sad
_cod_depositor_comments
'Adding full bibliography for 7705390--7705397.cif.'
_cod_original_cell_volume        15433(5)
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_database_code               7705390
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C3(H3)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C15(H15A,H15B,
 H15C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'y, x, -z+1/2'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'-y, -x, z-1/2'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
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 0.60731(2) 0.66667 0.4167 0.0356(3) Uani 1 2 d S T P . .
O1 O 0.54687(10) 0.63961(11) 0.46986(13) 0.0450(7) Uani 1 1 d . . . . .
O2 O 0.48589(12) 0.49835(10) 0.67065(12) 0.0514(7) Uani 1 1 d . . . . .
N1 N 0.62036(11) 0.60820(11) 0.43440(12) 0.0344(7) Uani 1 1 d . . . . .
C6 C 0.49326(13) 0.59939(14) 0.56215(16) 0.0369(8) Uani 1 1 d . . . . .
C1 C 0.53328(14) 0.60544(14) 0.51676(16) 0.0379(8) Uani 1 1 d . . . . .
C2 C 0.55633(14) 0.57347(13) 0.52438(16) 0.0356(8) Uani 1 1 d . . . . .
C16 C 0.71455(14) 0.63690(14) 0.42345(17) 0.0381(8) Uani 1 1 d . . . . .
H16A H 0.7372 0.6230 0.4083 0.046 Uiso 1 1 calc R . . . .
H16B H 0.7117 0.6324 0.4711 0.046 Uiso 1 1 calc R . . . .
C8 C 0.46401(16) 0.62961(16) 0.5531(2) 0.0494(10) Uani 1 1 d . . . . .
C5 C 0.48171(14) 0.56416(14) 0.61187(16) 0.0401(8) Uani 1 1 d . . . . .
H5 H 0.4570 0.5613 0.6435 0.048 Uiso 1 1 calc R . . . .
C7 C 0.59488(14) 0.57458(13) 0.48063(16) 0.0370(8) Uani 1 1 d . . . . .
H7 H 0.6029 0.5473 0.4860 0.044 Uiso 1 1 calc R . . . .
C4 C 0.50409(15) 0.53235(14) 0.61858(16) 0.0405(8) Uani 1 1 d . . . . .
C11 C 0.50197(19) 0.68915(17) 0.5526(2) 0.0622(12) Uani 1 1 d . . . . .
H11A H 0.5204 0.7000 0.5942 0.093 Uiso 1 1 calc GR . . . .
H11B H 0.4822 0.7074 0.5457 0.093 Uiso 1 1 calc GR . . . .
H11C H 0.5276 0.6981 0.5177 0.093 Uiso 1 1 calc GR . . . .
C14 C 0.65432(15) 0.61389(16) 0.32482(18) 0.0445(9) Uani 1 1 d . . . . .
H14A H 0.6204 0.5867 0.3075 0.067 Uiso 1 1 calc GR . . . .
H14B H 0.6829 0.6150 0.2991 0.067 Uiso 1 1 calc GR . . . .
H14C H 0.6563 0.6482 0.3227 0.067 Uiso 1 1 calc GR . . . .
C13 C 0.65958(14) 0.60110(14) 0.39551(19) 0.0383(9) Uani 1 1 d . . . . .
C3 C 0.54037(15) 0.53622(14) 0.57499(17) 0.0397(8) Uani 1 1 d . . . . .
H3 H 0.5550 0.5139 0.5785 0.048 Uiso 1 1 calc R . . . .
C12 C 0.50156(18) 0.45971(16) 0.67423(19) 0.0495(10) Uani 1 1 d . . . . .
H12A H 0.4907 0.4384 0.6347 0.074 Uiso 1 1 calc GR . . . .
H12B H 0.4849 0.4370 0.7118 0.074 Uiso 1 1 calc GR . . . .
H12C H 0.5399 0.4771 0.6786 0.074 Uiso 1 1 calc GR . . . .
C15 C 0.65002(17) 0.54524(15) 0.3979(2) 0.0508(10) Uani 1 1 d . . . . .
H15A H 0.6594 0.5383 0.4409 0.076 Uiso 1 1 calc GR . . . .
H15B H 0.6717 0.5410 0.3651 0.076 Uiso 1 1 calc GR . . . .
H15C H 0.6128 0.5204 0.3893 0.076 Uiso 1 1 calc GR . . . .
C9 C 0.4334(2) 0.6120(2) 0.4881(2) 0.0681(13) Uani 1 1 d . . . . .
H9A H 0.4580 0.6183 0.4527 0.102 Uiso 1 1 calc GR . . . .
H9B H 0.4155 0.6321 0.4805 0.102 Uiso 1 1 calc GR . . . .
H9C H 0.4074 0.5744 0.4902 0.102 Uiso 1 1 calc GR . . . .
C10 C 0.42407(19) 0.6181(2) 0.6078(3) 0.0657(12) Uani 1 1 d . . . . .
H10A H 0.3990 0.5802 0.6094 0.099 Uiso 1 1 calc GR . . . .
H10B H 0.4051 0.6371 0.5995 0.099 Uiso 1 1 calc GR . . . .
H10C H 0.4426 0.6295 0.6492 0.099 Uiso 1 1 calc GR . . . .
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'
Cu Cu 0.3201 1.2651 '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'
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 86.49(15) . 11_565 ?
O1 Cu1 N1 147.24(12) . 11_565 ?
O1 Cu1 N1 147.24(12) 11_565 . ?
O1 Cu1 N1 94.39(11) . . ?
O1 Cu1 N1 94.39(11) 11_565 11_565 ?
N1 Cu1 N1 101.93(17) 11_565 . ?
C1 O1 Cu1 128.0(2) . . ?
C4 O2 C12 117.0(3) . . ?
C7 N1 Cu1 120.4(2) . . ?
C7 N1 C13 118.4(3) . . ?
C13 N1 Cu1 121.2(2) . . ?
C1 C6 C8 120.7(3) . . ?
C5 C6 C1 117.2(3) . . ?
C5 C6 C8 122.1(3) . . ?
O1 C1 C6 119.6(3) . . ?
O1 C1 C2 121.9(3) . . ?
C2 C1 C6 118.5(3) . . ?
C1 C2 C7 123.3(3) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 C7 115.8(3) . . ?
C16 C16 H16A 107.1 11_565 . ?
C16 C16 H16B 107.1 11_565 . ?
H16A C16 H16B 106.8 . . ?
C13 C16 C16 121.1(3) . 11_565 ?
C13 C16 H16A 107.1 . . ?
C13 C16 H16B 107.1 . . ?
C6 C8 C11 111.4(3) . . ?
C6 C8 C9 108.2(3) . . ?
C6 C8 C10 111.8(3) . . ?
C11 C8 C9 110.1(4) . . ?
C11 C8 C10 107.2(4) . . ?
C10 C8 C9 108.0(4) . . ?
C6 C5 H5 118.0 . . ?
C6 C5 C4 123.9(3) . . ?
C4 C5 H5 118.0 . . ?
N1 C7 C2 128.6(3) . . ?
N1 C7 H7 115.7 . . ?
C2 C7 H7 115.7 . . ?
O2 C4 C5 114.9(3) . . ?
C3 C4 O2 125.6(3) . . ?
C3 C4 C5 119.5(3) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
N1 C13 C16 108.8(3) . . ?
N1 C13 C14 107.3(3) . . ?
N1 C13 C15 113.0(3) . . ?
C16 C13 C14 113.0(3) . . ?
C15 C13 C16 106.9(3) . . ?
C15 C13 C14 108.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.0 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 1.892(2) . ?
Cu1 O1 1.892(2) 11_565 ?
Cu1 N1 1.972(3) 11_565 ?
Cu1 N1 1.972(3) . ?
O1 C1 1.306(4) . ?
O2 C4 1.381(4) . ?
O2 C12 1.424(5) . ?
N1 C7 1.307(4) . ?
N1 C13 1.502(4) . ?
C6 C1 1.443(5) . ?
C6 C8 1.524(5) . ?
C6 C5 1.375(5) . ?
C1 C2 1.415(5) . ?
C2 C7 1.436(5) . ?
C2 C3 1.413(5) . ?
C16 C16 1.540(7) 11_565 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C13 1.532(5) . ?
C8 C11 1.534(6) . ?
C8 C9 1.553(6) . ?
C8 C10 1.538(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.392(6) . ?
C7 H7 0.9500 . ?
C4 C3 1.356(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 C13 1.535(5) . ?
C13 C15 1.521(5) . ?
C3 H3 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.126 1025.3 341.2 ?
2 0.333 0.667 -0.376 1025.3 341.2 ?
3 0.667 0.333 -0.710 1025.3 341.2 ?
