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#$Date: 2021-10-07 11:35:34 +0300 (Thu, 07 Oct 2021) $
#$Revision: 269849 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/48/1564885.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_1564885
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_absolute_configuration ad
_chemical_formula_sum            'C10 H13 Cu N5 O4 S2'
_chemical_formula_weight         394.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_Hall           'C -2y'
_space_group_name_H-M_alt        'C 1 m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 99.2339(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6665(7)
_cell_length_b                   12.4100(7)
_cell_length_c                   4.8699(3)
_cell_measurement_reflns_used    3891
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.68
_cell_measurement_theta_min      3.26
_cell_volume                     755.59(8)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4690
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         3.259
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    1.746
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_description       column
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   .
_exptl_transmission_factor_min   .
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 616 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.054(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1609
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0339
_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)+(0.0270P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0602
_reflns_Friedel_coverage         0.969
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                1461
_reflns_number_total             1609
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            9.cif
_cod_data_source_block           9
_cod_original_sg_symbol_H-M      'C m'
_cod_database_code               1564885
_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   0.709
_shelx_estimated_absorpt_t_max   0.930
_exptl_absorpt_special_details   .
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, 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 0.62315(5) 0.500000 0.40848(8) 0.0184(3) Uani 1 2 d S T P . .
S1 S 0.82389(17) 0.500000 -0.0351(4) 0.0274(5) Uani 1 2 d S T P . .
S2 S 0.48227(14) 0.500000 0.7336(3) 0.0167(4) Uani 1 2 d S T P . .
O1 O 0.5383(3) 0.4060(3) 0.6243(6) 0.0208(9) Uani 1 1 d . . . . .
O2 O 0.3700(4) 0.500000 0.6199(10) 0.0235(12) Uani 1 2 d S T P . .
O3 O 0.4978(4) 0.500000 1.0352(10) 0.0270(11) Uani 1 2 d S T P . .
N1 N 0.7181(3) 0.6153(3) 0.3192(8) 0.0200(9) Uani 1 1 d . . . . .
N2 N 0.8547(3) 0.6993(3) 0.1923(8) 0.0234(9) Uani 1 1 d . . . . .
C1 C 0.7972(4) 0.6075(4) 0.1737(10) 0.0202(11) Uani 1 1 d . . . . .
C2 C 0.8095(4) 0.7694(4) 0.3585(10) 0.0276(12) Uani 1 1 d . . . . .
H2 H 0.832167 0.840789 0.407463 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7268(4) 0.7163(4) 0.4377(10) 0.0266(12) Uani 1 1 d . . . . .
H3 H 0.681201 0.744386 0.557414 0.032 Uiso 1 1 calc R U . . .
C4 C 0.9507(4) 0.7206(5) 0.0718(10) 0.0340(13) Uani 1 1 d . . . . .
H4A H 1.004277 0.664970 0.132578 0.051 Uiso 1 1 calc R U . . .
H4B H 0.979458 0.791402 0.133374 0.051 Uiso 1 1 calc R U . . .
H4C H 0.932841 0.719685 -0.131575 0.051 Uiso 1 1 calc R U . . .
N3 N 0.0455(10) 0.500000 0.544(2) 0.101(4) Uani 1 2 d S T P . .
C5 C 0.1070(8) 0.500000 0.734(2) 0.044(3) Uani 1 2 d S TU P . .
C6 C 0.1849(8) 0.500000 0.976(2) 0.080(4) Uani 1 2 d S T P . .
H6A H 0.188978 0.571872 1.060359 0.120 Uiso 0.5 1 calc R U P A -1
H6B H 0.254553 0.480893 0.926803 0.120 Uiso 0.5 1 calc R U P A -1
H6C H 0.165232 0.447235 1.108721 0.120 Uiso 0.5 1 calc R U P A -1
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 93.6(2) . 2_565
N1 Cu1 O1 160.72(14) . .
N1 Cu1 O1 95.24(14) 2_565 .
N1 Cu1 O1 95.24(14) . 2_565
N1 Cu1 O1 160.72(14) 2_565 2_565
O1 Cu1 O1 71.56(17) . 2_565
N1 Cu1 O3 101.67(15) . 1_554
N1 Cu1 O3 101.67(15) 2_565 1_554
O1 Cu1 O3 93.26(14) . 1_554
O1 Cu1 O3 93.26(14) 2_565 1_554
N1 Cu1 S2 130.37(11) . .
N1 Cu1 S2 130.37(12) 2_565 .
O1 Cu1 S2 35.85(9) . .
O1 Cu1 S2 35.85(9) 2_565 .
O3 Cu1 S2 91.64(13) 1_554 .
C1 S1 C1 99.9(3) 2_565 .
O2 S2 O3 110.8(3) . .
O2 S2 O1 110.88(18) . .
O3 S2 O1 111.25(18) . .
O2 S2 O1 110.88(18) . 2_565
O3 S2 O1 111.25(18) . 2_565
O1 S2 O1 101.5(3) . 2_565
O2 S2 Cu1 120.2(2) . .
O3 S2 Cu1 129.0(2) . .
O1 S2 Cu1 50.87(12) . .
O1 S2 Cu1 50.87(12) 2_565 .
S2 O1 Cu1 93.28(16) . .
S2 O3 Cu1 142.6(3) . 1_556
C1 N1 C3 105.9(4) . .
C1 N1 Cu1 127.7(3) . .
C3 N1 Cu1 125.6(3) . .
C1 N2 C2 107.7(4) . .
C1 N2 C4 127.1(4) . .
C2 N2 C4 125.1(4) . .
N1 C1 N2 110.6(4) . .
N1 C1 S1 127.1(4) . .
N2 C1 S1 122.2(4) . .
C3 C2 N2 106.0(4) . .
C3 C2 H2 127.0 . .
N2 C2 H2 127.0 . .
C2 C3 N1 109.8(5) . .
C2 C3 H3 125.1 . .
N1 C3 H3 125.1 . .
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 C6 179.9(13) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 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 1.962(4) .
Cu1 N1 1.962(4) 2_565
Cu1 O1 1.996(3) .
Cu1 O1 1.996(3) 2_565
Cu1 O3 2.213(5) 1_554
Cu1 S2 2.5687(18) .
S1 C1 1.743(5) 2_565
S1 C1 1.743(5) .
S2 O2 1.440(5) .
S2 O3 1.450(5) .
S2 O1 1.507(3) .
S2 O1 1.507(3) 2_565
N1 C1 1.321(6) .
N1 C3 1.378(6) .
N2 C1 1.347(6) .
N2 C2 1.374(6) .
N2 C4 1.456(6) .
C2 C3 1.346(7) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
N3 C5 1.109(14) .
C5 C6 1.409(14) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 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
C2 H2 O2 0.95 2.25 3.176(5) 165.9 3
C4 H4B O3 0.98 2.65 3.528(6) 149.3 3_554
C6 H6B O2 0.98 2.27 3.133(11) 146.9 .
