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#$Date: 2021-10-07 11:36:58 +0300 (Thu, 07 Oct 2021) $
#$Revision: 269850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/48/1564886.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_1564886
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            'C9 H16 Cu N5 O4 S2'
_chemical_formula_weight         385.93
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.539(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.3614(8)
_cell_length_b                   13.9033(7)
_cell_length_c                   6.9472(3)
_cell_measurement_reflns_used    9509
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.19
_cell_measurement_theta_min      2.52
_cell_volume                     1562.81(13)
_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 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0312
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            45916
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.989
_diffrn_reflns_theta_min         2.518
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    1.686
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_description       column
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.566
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.167
_exptl_transmission_factor_max   .
_exptl_transmission_factor_min   .
_refine_diff_density_max         1.369
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         4546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0282
_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)+(0.0292P)²+1.9117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0711
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4219
_reflns_number_total             4546
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            10.cif
_cod_data_source_block           10
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1564886
_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   0.449
_shelx_estimated_absorpt_t_max   0.766
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
Cu1 Cu 0.29974(2) 0.71305(2) 0.77265(3) 0.01635(6) Uani 1 1 d . . . . .
S1 S 0.23807(2) 0.81407(3) 0.54013(6) 0.01717(8) Uani 1 1 d . . . . .
S2 S 0.42567(2) 0.65057(3) 0.78724(5) 0.01722(8) Uani 1 1 d . . . . .
N3 N 0.50255(8) 0.62671(9) 0.46662(19) 0.0153(2) Uani 1 1 d . . . . .
N4 N 0.37609(8) 0.57771(10) 0.42034(19) 0.0160(2) Uani 1 1 d . . . . .
H4 H 0.3254 0.5640 0.4397 0.019 Uiso 1 1 calc R U . . .
N2 N 0.10832(9) 0.68603(11) 0.4622(2) 0.0218(3) Uani 1 1 d . . . . .
H2 H 0.1379 0.6341 0.4949 0.026 Uiso 1 1 calc R U . . .
N1 N 0.07352(8) 0.83458(11) 0.4094(2) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.13764(9) 0.77611(12) 0.4715(2) 0.0172(3) Uani 1 1 d . . . . .
C5 C 0.43401(9) 0.61948(11) 0.5522(2) 0.0137(3) Uani 1 1 d . . . . .
C6 C 0.48695(10) 0.58999(12) 0.2792(2) 0.0193(3) Uani 1 1 d . . . . .
H6 H 0.5249 0.5870 0.1884 0.023 Uiso 1 1 calc R U . . .
C7 C 0.40797(10) 0.55941(12) 0.2496(2) 0.0194(3) Uani 1 1 d . . . . .
H7 H 0.3796 0.5309 0.1344 0.023 Uiso 1 1 calc R U . . .
C2 C 0.00263(10) 0.77990(15) 0.3601(3) 0.0257(4) Uani 1 1 d . . . . .
H2A H -0.0511 0.8033 0.3120 0.031 Uiso 1 1 calc R U . . .
C8 C 0.57913(10) 0.67272(13) 0.5529(3) 0.0226(3) Uani 1 1 d . . . . .
H8A H 0.5732 0.7427 0.5408 0.034 Uiso 1 1 calc R U . . .
H8B H 0.6243 0.6512 0.4853 0.034 Uiso 1 1 calc R U . . .
H8C H 0.5914 0.6553 0.6909 0.034 Uiso 1 1 calc R U . . .
C3 C 0.02454(11) 0.68718(16) 0.3935(3) 0.0273(4) Uani 1 1 d . . . . .
H3 H -0.0109 0.6329 0.3735 0.033 Uiso 1 1 calc R U . . .
C4 C 0.08020(11) 0.93880(14) 0.3914(3) 0.0278(4) Uani 1 1 d . . . . .
H4A H 0.0925 0.9675 0.5213 0.042 Uiso 1 1 calc R U . . .
H4B H 0.0279 0.9646 0.3245 0.042 Uiso 1 1 calc R U . . .
H4C H 0.1247 0.9542 0.3164 0.042 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
S2 Cu1 S1 125.944(17) . .
S2 Cu1 S1 114.737(16) . 4_576
S1 Cu1 S1 118.787(17) . 4_576
C1 S1 Cu1 108.24(6) . .
C1 S1 Cu1 104.11(5) . 4_575
Cu1 S1 Cu1 105.999(18) . 4_575
C5 S2 Cu1 105.03(5) . .
C5 N3 C6 109.70(13) . .
C5 N3 C8 124.95(14) . .
C6 N3 C8 125.19(14) . .
C5 N4 C7 110.12(13) . .
C5 N4 H4 124.9 . .
C7 N4 H4 124.9 . .
C1 N2 C3 109.60(16) . .
C1 N2 H2 125.2 . .
C3 N2 H2 125.2 . .
C1 N1 C2 109.36(15) . .
C1 N1 C4 124.20(15) . .
C2 N1 C4 126.41(15) . .
N2 C1 N1 107.02(14) . .
N2 C1 S1 128.27(13) . .
N1 C1 S1 124.67(13) . .
N4 C5 N3 106.23(13) . .
N4 C5 S2 127.49(12) . .
N3 C5 S2 126.16(12) . .
C7 C6 N3 107.35(14) . .
C7 C6 H6 126.3 . .
N3 C6 H6 126.3 . .
C6 C7 N4 106.58(14) . .
C6 C7 H7 126.7 . .
N4 C7 H7 126.7 . .
C3 C2 N1 106.88(15) . .
C3 C2 H2A 126.6 . .
N1 C2 H2A 126.6 . .
N3 C8 H8A 109.5 . .
N3 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N3 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C2 C3 N2 107.14(16) . .
C2 C3 H3 126.4 . .
N2 C3 H3 126.4 . .
N1 C4 H4A 109.5 . .
N1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
N1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 S2 2.2243(4) .
Cu1 S1 2.2620(4) .
Cu1 S1 2.2738(4) 4_576
S1 C1 1.7243(16) .
S1 Cu1 2.2739(4) 4_575
S2 C5 1.7143(15) .
N3 C5 1.3487(19) .
N3 C6 1.387(2) .
N3 C8 1.455(2) .
N4 C5 1.3477(19) .
N4 C7 1.388(2) .
N4 H4 0.8800 .
N2 C1 1.339(2) .
N2 C3 1.383(2) .
N2 H2 0.8800 .
N1 C1 1.347(2) .
N1 C2 1.387(2) .
N1 C4 1.460(2) .
C6 C7 1.347(2) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C2 C3 1.349(3) .
C2 H2A 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C3 H3 0.9500 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
