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#$Date: 2021-10-07 11:27:23 +0300 (Thu, 07 Oct 2021) $
#$Revision: 269844 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/48/1564880.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_1564880
loop_
_publ_author_name
'Murphy, Jaime M.'
'Gaertner, Andrea A.E.'
'Owen, Amanda M.'
'Struder, Samantha'
'McMillen, Colin D.'
'Wetzler, Modi'
'Brumaghim, Julia L.'
_publ_section_title
;
 Coordination complexes of methimazole with copper: Controlling redox
 reactions and sulfur extrusion
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119568
_journal_paper_doi               10.1016/j.ica.2020.119568
_journal_volume                  507
_journal_year                    2020
_chemical_formula_sum            'C16 H26 Cu N8 O10 S4'
_chemical_formula_weight         682.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                84.5081(19)
_cell_angle_beta                 87.5770(19)
_cell_angle_gamma                89.586(2)
_cell_formula_units_Z            1
_cell_length_a                   8.0915(4)
_cell_length_b                   8.6847(5)
_cell_length_c                   9.5541(5)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.52
_cell_volume                     667.71(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29160
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.531
_diffrn_reflns_theta_min         2.143
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    1.197
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_description       column
_exptl_crystal_F_000             351
_exptl_crystal_size_max          0.339
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.046
_exptl_transmission_factor_max   .
_exptl_transmission_factor_min   .
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0518P)²+0.2618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3698
_reflns_number_total             4055
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            4.cif
_cod_data_source_block           4
_cod_database_code               1564880
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_min   0.687
_shelx_estimated_absorpt_t_max   0.947
loop_
_space_group_symop_operation_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_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 0.500000 0.000000 0.500000 0.02651(9) Uani 1 2 d S . P . .
S1 S 0.18536(5) 0.28011(5) 0.43590(5) 0.03337(10) Uani 1 1 d . . . . .
S2 S 0.99160(5) 0.14516(6) 0.81448(5) 0.03757(11) Uani 1 1 d . . . . .
O1 O 0.8476(2) 0.1443(2) 0.92726(19) 0.0613(5) Uani 1 1 d . . . . .
H1 H 0.840447 0.058183 0.970511 0.092 Uiso 1 1 calc R U . . .
O2 O 1.14134(18) 0.1068(2) 0.88996(17) 0.0533(4) Uani 1 1 d . . . . .
O3 O 0.9916(3) 0.2998(2) 0.7462(2) 0.0711(5) Uani 1 1 d . . . . .
O4 O 0.9547(2) 0.0293(2) 0.72236(19) 0.0624(5) Uani 1 1 d . . . . .
O5W O 0.78755(17) 0.09000(16) 0.45847(17) 0.0417(3) Uani 1 1 d D . . . .
H5A H 0.844(4) 0.059(4) 0.392(2) 0.072(10) Uiso 1 1 d D . . . .
H5B H 0.839(3) 0.085(4) 0.534(2) 0.066(9) Uiso 1 1 d D . . . .
N1 N 0.43997(16) 0.11797(16) 0.31812(14) 0.0288(3) Uani 1 1 d . . . . .
N2 N 0.3045(2) 0.27240(17) 0.16558(15) 0.0357(3) Uani 1 1 d . . . . .
N3 N 0.45103(16) 0.19285(15) 0.59556(14) 0.0284(2) Uani 1 1 d . . . . .
N4 N 0.34812(18) 0.42248(16) 0.63109(16) 0.0333(3) Uani 1 1 d . . . . .
C1 C 0.31703(19) 0.21918(17) 0.30194(16) 0.0278(3) Uani 1 1 d . . . . .
C2 C 0.5110(2) 0.1081(2) 0.18560(18) 0.0357(3) Uani 1 1 d . . . . .
H2 H 0.602068 0.047325 0.164422 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4268(3) 0.2010(2) 0.09111(19) 0.0416(4) Uani 1 1 d . . . . .
H3 H 0.447799 0.214036 -0.005738 0.050 Uiso 1 1 calc R U . . .
C4 C 0.1794(4) 0.3798(3) 0.1074(3) 0.0586(6) Uani 1 1 d . . . . .
H4A H 0.074910 0.327892 0.109268 0.088 Uiso 1 1 calc R U . . .
H4B H 0.211651 0.415674 0.012069 0.088 Uiso 1 1 calc R U . . .
H4C H 0.169673 0.466315 0.162700 0.088 Uiso 1 1 calc R U . . .
C5 C 0.33597(18) 0.29748(17) 0.55922(16) 0.0267(3) Uani 1 1 d . . . . .
C6 C 0.5417(2) 0.2557(2) 0.69457(18) 0.0352(3) Uani 1 1 d . . . . .
H6 H 0.632263 0.209191 0.738414 0.042 Uiso 1 1 calc R U . . .
C7 C 0.4781(2) 0.3960(2) 0.7180(2) 0.0390(4) Uani 1 1 d . . . . .
H7 H 0.515417 0.461941 0.781011 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2427(3) 0.5602(2) 0.6221(3) 0.0493(5) Uani 1 1 d . . . . .
H8A H 0.215490 0.586897 0.525918 0.074 Uiso 1 1 calc R U . . .
H8B H 0.300402 0.644610 0.655735 0.074 Uiso 1 1 calc R U . . .
H8C H 0.143000 0.539540 0.678607 0.074 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'
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'
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
N1 Cu1 N1 180.0 . 2_656
N1 Cu1 N3 88.09(5) . .
N1 Cu1 N3 91.91(5) 2_656 .
N1 Cu1 N3 91.91(5) . 2_656
N1 Cu1 N3 88.09(5) 2_656 2_656
N3 Cu1 N3 180.0 . 2_656
C5 S1 C1 97.21(7) . .
O3 S2 O4 113.42(13) . .
O3 S2 O2 113.27(12) . .
O4 S2 O2 111.41(12) . .
O3 S2 O1 104.39(12) . .
O4 S2 O1 107.10(12) . .
O2 S2 O1 106.56(10) . .
S2 O1 H1 109.5 . .
H5A O5W H5B 112(3) . .
C1 N1 C2 105.96(13) . .
C1 N1 Cu1 125.77(11) . .
C2 N1 Cu1 128.23(11) . .
C1 N2 C3 106.90(14) . .
C1 N2 C4 126.47(17) . .
C3 N2 C4 126.57(17) . .
C5 N3 C6 105.80(13) . .
C5 N3 Cu1 125.50(11) . .
C6 N3 Cu1 128.04(11) . .
C5 N4 C7 106.94(14) . .
C5 N4 C8 127.38(17) . .
C7 N4 C8 125.67(16) . .
N1 C1 N2 111.10(14) . .
N1 C1 S1 126.17(12) . .
N2 C1 S1 122.73(12) . .
C3 C2 N1 109.07(16) . .
C3 C2 H2 125.5 . .
N1 C2 H2 125.5 . .
C2 C3 N2 106.95(15) . .
C2 C3 H3 126.5 . .
N2 C3 H3 126.5 . .
N2 C4 H4A 109.5 . .
N2 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
N2 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
N3 C5 N4 111.14(14) . .
N3 C5 S1 126.02(12) . .
N4 C5 S1 122.84(12) . .
C7 C6 N3 109.18(15) . .
C7 C6 H6 125.4 . .
N3 C6 H6 125.4 . .
C6 C7 N4 106.94(15) . .
C6 C7 H7 126.5 . .
N4 C7 H7 126.5 . .
N4 C8 H8A 109.5 . .
N4 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N4 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.0072(13) .
Cu1 N1 2.0072(13) 2_656
Cu1 N3 2.0120(13) .
Cu1 N3 2.0120(13) 2_656
S1 C5 1.7476(16) .
S1 C1 1.7491(16) .
S2 O3 1.4356(19) .
S2 O4 1.4393(18) .
S2 O2 1.4564(15) .
S2 O1 1.5528(16) .
O1 H1 0.8200 .
O5W H5A 0.830(17) .
O5W H5B 0.840(17) .
N1 C1 1.3268(19) .
N1 C2 1.378(2) .
N2 C1 1.348(2) .
N2 C3 1.373(3) .
N2 C4 1.462(2) .
N3 C5 1.3296(19) .
N3 C6 1.376(2) .
N4 C5 1.345(2) .
N4 C7 1.372(2) .
N4 C8 1.462(2) .
C2 C3 1.355(3) .
C2 H2 0.9300 .
C3 H3 0.9300 .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C6 C7 1.354(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
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
O1 H1 O2 0.82 1.87 2.663(3) 162.2 2_757
O5W H5A O4 0.830(17) 2.10(2) 2.901(2) 161(3) 2_756
O5W H5B O4 0.840(17) 2.083(18) 2.913(2) 170(3) .
