#------------------------------------------------------------------------------
#$Date: 2024-04-05 02:17:35 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290915 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/50/7715059.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_7715059
loop_
_publ_author_name
'Ogawa, Mana'
'Usami, Sayaka'
'Takahama, Ryo'
'Iwamoto, Kazuko'
'Nabeta, Tomomi'
'Kawashima, Shin'
'Kojima, Ryoichi'
'Ohyama, Junya'
'Hayakawa, Teruaki'
'Nabae, Yuta'
'Moriya, Makoto'
_publ_section_title
;
 One-pot gram-scale rapid synthesis of MN₄ complexes with
 14-membered ring macrocyclic ligand as a precursor for carbon-based ORR
 and CO₂RR catalysts.
;
_journal_issue                   10
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4426
_journal_page_last               4431
_journal_paper_doi               10.1039/d3dt04129h
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C24 H12 Cu N6, 2(C F3 O3 S)'
_chemical_formula_sum            'C26 H12 Cu F6 N6 O6 S2'
_chemical_formula_weight         746.08
_chemical_name_systematic        '[Cu(H2HAM)(OTf)2]'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-12
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-10-12 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.020(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5956(2)
_cell_length_b                   18.2474(4)
_cell_length_c                   8.9518(2)
_cell_measurement_reflns_used    11340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3040
_cell_measurement_theta_min      2.2230
_cell_volume                     1349.54(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -44.00   0.50   10.00    --    5.00  45.00 120.00   80
  2  ω     57.00  94.00   0.50   10.00    --    5.00  45.00 120.00   74
  3  ω     -9.00  16.00   0.50   10.00    --    5.00  45.00 120.00   50
  4  ω    -65.00 -38.00   0.50   10.00    --    5.00  45.00   0.00   54
  5  ω     58.00  92.00   0.50   10.00    --    5.00  45.00   0.00   68
  6  ω    -33.00   2.00   0.50   10.00    --    5.00  45.00  90.00   70
  7  ω     69.00  94.00   0.50   10.00    --    5.00  45.00  90.00   50
  8  ω    -96.00  82.00   0.50   10.00    --   -7.10  45.00  30.00  356
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17249
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.216
_diffrn_reflns_theta_min         2.232
_exptl_absorpt_coefficient_mu    1.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_description       block
_exptl_crystal_F_000             746
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0408
_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)+(0.0653P)²+0.8613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3225
_reflns_number_total             3486
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt04129h2.cif
_cod_data_source_block           201109-tkh-n-aza-cu-otf-meoh
_cod_depositor_comments
'Adding full bibliography for 7715057--7715059.cif.'
_cod_database_code               7715059
_shelx_shelxl_version_number     2018/3
_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
2.a Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00J(H00J), C00L(H00L), C00N(H00N), C00O(H00O)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cu Cu 0.500000 0.500000 0.500000 0.02206(12) Uani 1 2 d S . P . .
S002 S 0.68006(5) 0.63563(2) 0.80824(5) 0.02218(13) Uani 1 1 d . . . . .
F003 F 0.41880(15) 0.70078(7) 0.64344(17) 0.0394(3) Uani 1 1 d . . . . .
F004 F 0.63100(18) 0.76687(7) 0.68631(18) 0.0428(3) Uani 1 1 d . . . . .
O005 O 0.5848(2) 0.59261(8) 0.88686(17) 0.0325(3) Uani 1 1 d . . . . .
O006 O 0.68756(18) 0.60487(8) 0.66205(18) 0.0305(3) Uani 1 1 d . . . . .
F007 F 0.5190(2) 0.74886(9) 0.86813(18) 0.0580(5) Uani 1 1 d . . . . .
N008 N 0.33242(18) 0.51562(8) 0.59730(18) 0.0194(3) Uani 1 1 d . . . . .
N009 N 0.43466(19) 0.44034(9) 0.81468(18) 0.0213(3) Uani 1 1 d . . . . .
N00A N 0.61364(18) 0.43539(8) 0.65907(17) 0.0194(3) Uani 1 1 d . . . . .
O00B O 0.82972(19) 0.66287(11) 0.9064(2) 0.0450(4) Uani 1 1 d . . . . .
C00C C 0.5765(2) 0.41584(9) 0.7868(2) 0.0199(3) Uani 1 1 d . . . . .
C00D C 0.3196(2) 0.48869(10) 0.7303(2) 0.0201(3) Uani 1 1 d . . . . .
C00E C 0.7511(2) 0.41057(9) 0.6280(2) 0.0192(3) Uani 1 1 d . . . . .
C00F C 0.2204(2) 0.56370(9) 0.5131(2) 0.0193(3) Uani 1 1 d . . . . .
C00G C 0.8587(2) 0.36237(10) 0.7246(2) 0.0226(4) Uani 1 1 d . . . . .
C00H C 0.0877(2) 0.58801(10) 0.5595(2) 0.0229(4) Uani 1 1 d . . . . .
C00I C 0.6825(2) 0.36871(10) 0.8951(2) 0.0233(4) Uani 1 1 d . . . . .
H00I H 0.658572 0.355723 0.986789 0.028 Uiso 1 1 calc R U . . .
C00J C 0.8196(2) 0.34248(10) 0.8645(2) 0.0252(4) Uani 1 1 d . . . . .
H00J H 0.888121 0.311391 0.935415 0.030 Uiso 1 1 calc R U . . .
C00K C 0.0044(2) 0.66237(11) 0.3235(2) 0.0288(4) Uani 1 1 d . . . . .
C00L C 0.0747(2) 0.55886(11) 0.7040(2) 0.0267(4) Uani 1 1 d . . . . .
H00L H -0.010966 0.573198 0.742054 0.032 Uiso 1 1 calc R U . . .
C00M C 0.5560(2) 0.71730(11) 0.7494(2) 0.0250(4) Uani 1 1 d . . . . .
C00N C 0.1865(2) 0.51021(11) 0.7867(2) 0.0251(4) Uani 1 1 d . . . . .
H00N H 0.175903 0.491131 0.879729 0.030 Uiso 1 1 calc R U . . .
C00O C -0.0206(2) 0.63885(12) 0.4605(3) 0.0296(4) Uani 1 1 d . . . . .
H00O H -0.109611 0.656215 0.489855 0.036 Uiso 1 1 calc R U . . .
H009 H 0.416(3) 0.4288(14) 0.897(3) 0.025(6) 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'
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'
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'
S S 0.1246 0.1234 '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
N008 Cu N008 180.0 3_666 . ?
N00A Cu N008 92.73(6) 3_666 3_666 ?
N00A Cu N008 92.73(6) . . ?
N00A Cu N008 87.27(6) 3_666 . ?
N00A Cu N008 87.27(6) . 3_666 ?
N00A Cu N00A 180.0 . 3_666 ?
O005 S002 C00M 102.66(9) . . ?
O006 S002 O005 113.75(9) . . ?
O006 S002 C00M 103.02(9) . . ?
O00B S002 O005 114.97(11) . . ?
O00B S002 O006 115.76(11) . . ?
O00B S002 C00M 104.38(10) . . ?
C00D N008 Cu 128.32(13) . . ?
C00D N008 C00F 121.02(15) . . ?
C00F N008 Cu 110.61(12) . . ?
C00D N009 C00C 129.75(15) . . ?
C00C N00A Cu 128.38(12) . . ?
C00C N00A C00E 121.18(15) . . ?
C00E N00A Cu 110.42(11) . . ?
N009 C00C C00I 120.17(16) . . ?
N00A C00C N009 120.35(16) . . ?
N00A C00C C00I 119.47(17) . . ?
N008 C00D N009 120.33(16) . . ?
N008 C00D C00N 119.41(17) . . ?
N009 C00D C00N 120.26(17) . . ?
N00A C00E C00F 116.12(15) . 3_666 ?
N00A C00E C00G 123.25(16) . . ?
C00G C00E C00F 120.62(16) . 3_666 ?
N008 C00F C00E 115.55(15) . 3_666 ?
N008 C00F C00H 123.51(17) . . ?
C00H C00F C00E 120.93(16) . 3_666 ?
C00E C00G C00J 115.35(17) . . ?
C00E C00G C00K 118.21(18) . 3_666 ?
C00J C00G C00K 126.43(17) . 3_666 ?
C00F C00H C00L 115.25(17) . . ?
C00F C00H C00O 117.92(18) . . ?
C00L C00H C00O 126.83(17) . . ?
C00J C00I C00C 120.02(17) . . ?
C00I C00J C00G 120.66(17) . . ?
C00O C00K C00G 120.98(17) . 3_666 ?
C00N C00L C00H 120.83(17) . . ?
F003 C00M S002 110.73(13) . . ?
F004 C00M S002 111.49(14) . . ?
F004 C00M F003 106.93(16) . . ?
F007 C00M S002 112.02(13) . . ?
F007 C00M F003 108.08(18) . . ?
F007 C00M F004 107.37(18) . . ?
C00L C00N C00D 119.98(18) . . ?
C00K C00O C00H 121.30(18) . . ?
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
Cu N008 1.8992(15) 3_666 ?
Cu N008 1.8992(15) . ?
Cu N00A 1.8984(14) 3_666 ?
Cu N00A 1.8984(14) . ?
S002 O005 1.4489(15) . ?
S002 O006 1.4416(15) . ?
S002 O00B 1.4319(16) . ?
S002 C00M 1.824(2) . ?
F003 C00M 1.328(2) . ?
F004 C00M 1.325(2) . ?
F007 C00M 1.322(2) . ?
N008 C00D 1.320(2) . ?
N008 C00F 1.366(2) . ?
N009 C00C 1.384(2) . ?
N009 C00D 1.384(2) . ?
N00A C00C 1.318(2) . ?
N00A C00E 1.363(2) . ?
C00C C00I 1.422(2) . ?
C00D C00N 1.428(3) . ?
C00E C00F 1.431(2) 3_666 ?
C00E C00G 1.391(2) . ?
C00F C00H 1.390(2) . ?
C00G C00J 1.430(3) . ?
C00G C00K 1.433(3) 3_666 ?
C00H C00L 1.431(3) . ?
C00H C00O 1.434(3) . ?
C00I C00J 1.368(3) . ?
C00K C00O 1.372(3) . ?
C00L C00N 1.367(3) . ?
