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#$Date: 2021-10-07 11:24:27 +0300 (Thu, 07 Oct 2021) $
#$Revision: 269842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/48/1564878.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_1564878
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 H24 Cu N10 O8 S2'
_chemical_formula_weight         612.11
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.436(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6291(9)
_cell_length_b                   13.5838(16)
_cell_length_c                   10.3684(11)
_cell_measurement_reflns_used    9629
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.17
_cell_measurement_theta_min      2.50
_cell_volume                     1195.2(2)
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0390
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26649
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.830
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             630
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.056
_exptl_transmission_factor_max   .
_exptl_transmission_factor_min   .
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0253
_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)+(0.0257P)²+0.8480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0609
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2490
_reflns_number_total             2734
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            2.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1564878
_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.
;
_shelx_estimated_absorpt_t_min   0.872
_shelx_estimated_absorpt_t_max   0.938
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 0.5000 0.5000 0.5000 0.01088(8) Uani 1 2 d S . P . .
S1 S 0.74697(5) 0.65912(3) 0.35221(4) 0.01452(9) Uani 1 1 d . . . . .
O1W O 0.39800(13) 0.66733(9) 0.45511(11) 0.0185(2) Uani 1 1 d D . . . .
H1A H 0.461(2) 0.7152(15) 0.478(2) 0.040(7) Uiso 1 1 d D . . . .
H1B H 0.354(3) 0.6756(18) 0.3740(17) 0.045(7) Uiso 1 1 d D . . . .
O2 O 0.61456(14) 0.83176(9) 0.51776(11) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.83444(14) 0.85189(10) 0.65416(12) 0.0251(3) Uani 1 1 d . . . . .
O4 O 0.63145(17) 0.79263(10) 0.72263(12) 0.0312(3) Uani 1 1 d . . . . .
N1 N 0.57338(14) 0.48839(9) 0.32664(12) 0.0121(3) Uani 1 1 d . . . . .
N2 N 0.69452(15) 0.51967(9) 0.16042(12) 0.0127(3) Uani 1 1 d . . . . .
N3 N 0.71146(14) 0.55876(9) 0.57622(12) 0.0123(3) Uani 1 1 d . . . . .
N4 N 0.94066(15) 0.63419(10) 0.58805(12) 0.0146(3) Uani 1 1 d . . . . .
N5 N 0.69355(16) 0.82482(10) 0.63165(13) 0.0158(3) Uani 1 1 d . . . . .
C1 C 0.66692(17) 0.55046(11) 0.27812(14) 0.0118(3) Uani 1 1 d . . . . .
C2 C 0.61476(18) 0.43195(12) 0.13275(15) 0.0154(3) Uani 1 1 d . . . . .
H2 H 0.6109 0.3927 0.0564 0.018 Uiso 1 1 calc R U . . .
C3 C 0.54284(17) 0.41267(11) 0.23633(14) 0.0142(3) Uani 1 1 d . . . . .
H3 H 0.4812 0.3560 0.2453 0.017 Uiso 1 1 calc R U . . .
C4 C 0.79370(19) 0.56756(12) 0.07795(15) 0.0164(3) Uani 1 1 d . . . . .
H4A H 0.7274 0.6069 0.0102 0.025 Uiso 1 1 calc R U . . .
H4B H 0.8496 0.5173 0.0363 0.025 Uiso 1 1 calc R U . . .
H4C H 0.8704 0.6105 0.1323 0.025 Uiso 1 1 calc R U . . .
C5 C 0.80065(17) 0.61339(11) 0.51206(14) 0.0123(3) Uani 1 1 d . . . . .
C6 C 0.80039(18) 0.54401(12) 0.69949(15) 0.0150(3) Uani 1 1 d . . . . .
H6 H 0.7686 0.5064 0.7674 0.018 Uiso 1 1 calc R U . . .
C7 C 0.94040(18) 0.59156(12) 0.70861(15) 0.0171(3) Uani 1 1 d . . . . .
H7 H 1.0221 0.5948 0.7834 0.021 Uiso 1 1 calc R U . . .
C8 C 1.06994(19) 0.69121(14) 0.55141(17) 0.0220(4) Uani 1 1 d . . . . .
H8A H 1.0675 0.6848 0.4569 0.033 Uiso 1 1 calc R U . . .
H8B H 1.1707 0.6664 0.5994 0.033 Uiso 1 1 calc R U . . .
H8C H 1.0582 0.7607 0.5733 0.033 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'
S S 0.1246 0.1234 '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
N3 Cu1 N3 180.0 3_666 .
N3 Cu1 N1 91.58(5) 3_666 .
N3 Cu1 N1 88.42(5) . .
N3 Cu1 N1 88.42(5) 3_666 3_666
N3 Cu1 N1 91.58(5) . 3_666
N1 Cu1 N1 180.00(6) . 3_666
N3 Cu1 O1W 88.61(5) 3_666 3_666
N3 Cu1 O1W 91.39(5) . 3_666
N1 Cu1 O1W 86.38(4) . 3_666
N1 Cu1 O1W 93.62(4) 3_666 3_666
N3 Cu1 O1W 91.39(5) 3_666 .
N3 Cu1 O1W 88.61(5) . .
N1 Cu1 O1W 93.62(4) . .
N1 Cu1 O1W 86.38(4) 3_666 .
O1W Cu1 O1W 180.0 3_666 .
C1 S1 C5 97.59(7) . .
Cu1 O1W H1A 117.8(16) . .
Cu1 O1W H1B 112.6(16) . .
H1A O1W H1B 108(2) . .
C1 N1 C3 105.66(12) . .
C1 N1 Cu1 126.76(10) . .
C3 N1 Cu1 127.52(10) . .
C1 N2 C2 106.98(12) . .
C1 N2 C4 127.30(13) . .
C2 N2 C4 125.69(13) . .
C5 N3 C6 105.59(12) . .
C5 N3 Cu1 126.08(10) . .
C6 N3 Cu1 128.08(10) . .
C5 N4 C7 107.08(12) . .
C5 N4 C8 127.16(13) . .
C7 N4 C8 125.76(13) . .
O4 N5 O3 119.92(14) . .
O4 N5 O2 120.26(14) . .
O3 N5 O2 119.81(13) . .
N1 C1 N2 111.37(13) . .
N1 C1 S1 126.08(11) . .
N2 C1 S1 122.55(11) . .
C3 C2 N2 106.50(13) . .
C3 C2 H2 126.8 . .
N2 C2 H2 126.8 . .
C2 C3 N1 109.46(14) . .
C2 C3 H3 125.3 . .
N1 C3 H3 125.3 . .
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 111.30(13) . .
N3 C5 S1 126.36(11) . .
N4 C5 S1 122.29(11) . .
C7 C6 N3 109.48(14) . .
C7 C6 H6 125.3 . .
N3 C6 H6 125.3 . .
C6 C7 N4 106.52(13) . .
C6 C7 H7 126.7 . .
N4 C7 H7 126.7 . .
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 N3 2.0171(12) 3_666
Cu1 N3 2.0171(12) .
Cu1 N1 2.0172(12) .
Cu1 N1 2.0172(12) 3_666
Cu1 O1W 2.4514(12) 3_666
Cu1 O1W 2.4514(12) .
S1 C1 1.7474(15) .
S1 C5 1.7520(15) .
O1W H1A 0.853(16) .
O1W H1B 0.865(16) .
O2 N5 1.2554(17) .
O3 N5 1.2510(18) .
O4 N5 1.2455(18) .
N1 C1 1.3277(19) .
N1 C3 1.3837(19) .
N2 C1 1.3514(19) .
N2 C2 1.380(2) .
N2 C4 1.4669(19) .
N3 C5 1.3308(19) .
N3 C6 1.3811(19) .
N4 C5 1.3473(19) .
N4 C7 1.378(2) .
N4 C8 1.464(2) .
C2 C3 1.360(2) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C6 C7 1.358(2) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
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
O1W H1A O2 0.853(16) 2.058(16) 2.9092(17) 176(2) .
O1W H1B O3 0.865(16) 2.286(18) 3.0799(17) 153(2) 4_575
O1W H1B O4 0.865(16) 2.291(18) 3.0640(18) 149(2) 4_575
C2 H2 O3 0.95 2.38 3.271(2) 155.8 2_645
C3 H3 O4 0.95 2.29 3.233(2) 171.2 3_666
