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#$Date: 2021-10-07 11:32:55 +0300 (Thu, 07 Oct 2021) $
#$Revision: 269847 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/48/1564883.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_1564883
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 H14 Cu N4 O5 S2'
_chemical_formula_weight         385.90
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                95.449(3)
_cell_angle_beta                 104.276(3)
_cell_angle_gamma                96.167(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2792(7)
_cell_length_b                   9.7671(9)
_cell_length_c                   10.1282(9)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.91
_cell_volume                     688.27(11)
_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 0.999
_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  0.0376
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33902
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.574
_diffrn_reflns_theta_min         2.092
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    1.917
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.082
_exptl_transmission_factor_max   .
_exptl_transmission_factor_min   .
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.938
_refine_diff_density_rms         0.307
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         4212
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0266
_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)+(0.0648P)²+0.2394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3808
_reflns_number_total             4212
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            7.cif
_cod_data_source_block           7
_cod_database_code               1564883
_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   0.849
_shelx_estimated_absorpt_t_max   0.859
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 0.41674(3) 0.30082(2) 0.68135(2) 0.00748(8) Uani 1 1 d . . . . .
S2 S 0.72334(6) 0.22423(5) 0.82813(4) 0.00844(10) Uani 1 1 d . . . . .
S1 S 0.22600(7) 0.52816(5) 0.41901(4) 0.01025(11) Uani 1 1 d . . . . .
O1 O 0.6097(2) 0.33632(14) 0.86486(13) 0.0106(3) Uani 1 1 d . . . . .
O2 O 0.5945(2) 0.15635(14) 0.69101(13) 0.0112(3) Uani 1 1 d . . . . .
O4 O 0.7497(2) 0.12712(14) 0.92886(13) 0.0122(3) Uani 1 1 d . . . . .
O3 O 0.9056(2) 0.28780(16) 0.81008(15) 0.0154(3) Uani 1 1 d . . . . .
O5 O 0.1977(2) 0.17020(16) 0.74959(15) 0.0154(3) Uani 1 1 d D . . . .
H5 H 0.096(3) 0.208(3) 0.751(3) 0.036(9) Uiso 1 1 d D . . . .
N3 N 0.3251(2) 0.48167(17) 0.69480(16) 0.0096(3) Uani 1 1 d . . . . .
N4 N 0.2515(2) 0.68993(16) 0.65221(16) 0.0104(3) Uani 1 1 d . . . . .
N1 N 0.3119(2) 0.26500(16) 0.48225(16) 0.0092(3) Uani 1 1 d . . . . .
N2 N 0.2086(2) 0.28944(16) 0.26241(16) 0.0095(3) Uani 1 1 d . . . . .
C5 C 0.2718(3) 0.56210(18) 0.59767(18) 0.0087(3) Uani 1 1 d . . . . .
C6 C 0.3366(3) 0.5620(2) 0.81829(19) 0.0120(3) Uani 1 1 d . . . . .
H6 H 0.3702 0.5319 0.9065 0.014 Uiso 1 1 calc R U . . .
C7 C 0.2923(3) 0.6902(2) 0.79278(19) 0.0130(4) Uani 1 1 d . . . . .
H7 H 0.2899 0.7654 0.8588 0.016 Uiso 1 1 calc R U . . .
C8 C 0.1956(3) 0.8064(2) 0.5769(2) 0.0157(4) Uani 1 1 d . . . . .
H8A H 0.2438 0.8028 0.4946 0.024 Uiso 1 1 calc R U . . .
H8B H 0.2499 0.8941 0.6358 0.024 Uiso 1 1 calc R U . . .
H8C H 0.0558 0.8000 0.5499 0.024 Uiso 1 1 calc R U . . .
C1 C 0.2509(3) 0.35242(19) 0.39301(18) 0.0089(3) Uani 1 1 d . . . . .
C2 C 0.3074(3) 0.13951(19) 0.40338(19) 0.0113(3) Uani 1 1 d . . . . .
H2 H 0.3424 0.0566 0.4386 0.014 Uiso 1 1 calc R U . . .
C3 C 0.2452(3) 0.15393(19) 0.2682(2) 0.0119(3) Uani 1 1 d . . . . .
H3 H 0.2298 0.0845 0.1926 0.014 Uiso 1 1 calc R U . . .
C4 C 0.1471(3) 0.3538(2) 0.13656(19) 0.0128(4) Uani 1 1 d . . . . .
H4A H 0.0720 0.4280 0.1534 0.019 Uiso 1 1 calc R U . . .
H4B H 0.0684 0.2837 0.0631 0.019 Uiso 1 1 calc R U . . .
H4C H 0.2597 0.3929 0.1091 0.019 Uiso 1 1 calc R U . . .
C9 C 0.2567(3) 0.0943(2) 0.8643(2) 0.0173(4) Uani 1 1 d . . . . .
H9A H 0.3598 0.0422 0.8507 0.026 Uiso 1 1 calc R U . . .
H9B H 0.1478 0.0296 0.8713 0.026 Uiso 1 1 calc R U . . .
H9C H 0.3027 0.1593 0.9490 0.026 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
N1 Cu1 N3 93.40(6) . .
N1 Cu1 O2 95.31(6) . .
N3 Cu1 O2 160.84(7) . .
N1 Cu1 O1 159.78(7) . .
N3 Cu1 O1 95.41(6) . .
O2 Cu1 O1 71.29(6) . .
N1 Cu1 O5 100.35(6) . .
N3 Cu1 O5 100.82(6) . .
O2 Cu1 O5 94.35(6) . .
O1 Cu1 O5 95.82(6) . .
N1 Cu1 S2 128.15(5) . .
N3 Cu1 S2 128.54(5) . .
O2 Cu1 S2 35.82(4) . .
O1 Cu1 S2 35.75(4) . .
O5 Cu1 S2 99.70(4) . .
O4 S2 O3 112.14(9) . .
O4 S2 O1 111.56(8) . .
O3 S2 O1 109.74(9) . .
O4 S2 O2 111.60(8) . .
O3 S2 O2 110.09(8) . .
O1 S2 O2 101.19(8) . .
O4 S2 Cu1 131.24(6) . .
O3 S2 Cu1 116.62(6) . .
O1 S2 Cu1 50.84(5) . .
O2 S2 Cu1 50.83(5) . .
C1 S1 C5 102.97(8) . .
S2 O1 Cu1 93.40(7) . .
S2 O2 Cu1 93.35(7) . .
C9 O5 Cu1 119.43(12) . .
C9 O5 H5 113(2) . .
Cu1 O5 H5 114(2) . .
C5 N3 C6 105.78(15) . .
C5 N3 Cu1 129.37(13) . .
C6 N3 Cu1 123.99(13) . .
C5 N4 C7 107.07(15) . .
C5 N4 C8 126.78(16) . .
C7 N4 C8 126.15(16) . .
C1 N1 C2 105.68(15) . .
C1 N1 Cu1 129.59(13) . .
C2 N1 Cu1 124.38(13) . .
C1 N2 C3 107.34(16) . .
C1 N2 C4 126.87(16) . .
C3 N2 C4 125.68(16) . .
N3 C5 N4 111.26(16) . .
N3 C5 S1 130.72(14) . .
N4 C5 S1 118.02(14) . .
C7 C6 N3 109.25(16) . .
C7 C6 H6 125.4 . .
N3 C6 H6 125.4 . .
C6 C7 N4 106.63(16) . .
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 . .
N1 C1 N2 111.07(16) . .
N1 C1 S1 130.82(14) . .
N2 C1 S1 118.09(14) . .
C3 C2 N1 109.42(17) . .
C3 C2 H2 125.3 . .
N1 C2 H2 125.3 . .
C2 C3 N2 106.49(16) . .
C2 C3 H3 126.8 . .
N2 C3 H3 126.8 . .
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 . .
O5 C9 H9A 109.5 . .
O5 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
O5 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 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 1.9547(16) .
Cu1 N3 1.9587(16) .
Cu1 O2 2.0078(13) .
Cu1 O1 2.0083(13) .
Cu1 O5 2.2186(15) .
Cu1 S2 2.5854(5) .
S2 O4 1.4504(14) .
S2 O3 1.4638(15) .
S2 O1 1.5133(14) .
S2 O2 1.5156(14) .
S1 C1 1.7473(19) .
S1 C5 1.7493(18) .
O5 C9 1.439(2) .
O5 H5 0.863(18) .
N3 C5 1.326(2) .
N3 C6 1.391(2) .
N4 C5 1.355(2) .
N4 C7 1.380(2) .
N4 C8 1.467(2) .
N1 C1 1.332(2) .
N1 C2 1.391(2) .
N2 C1 1.352(2) .
N2 C3 1.382(2) .
N2 C4 1.467(2) .
C6 C7 1.359(3) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C2 C3 1.358(3) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 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
O5 H5 O3 0.863(18) 1.86(2) 2.692(2) 163(3) 1_455
C6 H6 O1 0.95 2.50 3.183(2) 128.6 2_667
C7 H7 O4 0.95 2.40 3.288(2) 155.9 2_667
C2 H2 O2 0.95 2.50 3.167(2) 127.4 2_656
C3 H3 O4 0.95 2.34 3.246(2) 159.1 2_656
