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#$Date: 2021-10-07 11:34:17 +0300 (Thu, 07 Oct 2021) $
#$Revision: 269848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/48/1564884.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_1564884
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            'C11 H19 Cu N4 O5.5 S3.5'
_chemical_formula_weight         471.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/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                 96.3480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4725(4)
_cell_length_b                   9.4873(3)
_cell_length_c                   15.3776(5)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.67
_cell_volume                     1808.48(10)
_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 0.999
_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  0.0387
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22581
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         2.665
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    1.645
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_description       tabular
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.031
_exptl_transmission_factor_max   .
_exptl_transmission_factor_min   .
_refine_diff_density_max         1.737
_refine_diff_density_min         -1.850
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0427
_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)+(0.0142P)²+8.1499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2805
_reflns_number_total             3276
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            8.cif
_cod_data_source_block           8
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_original_formula_sum        'C11 H19 Cu N4 O5.50 S3.50'
_cod_database_code               1564884
_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   0.518
_shelx_estimated_absorpt_t_max   0.951
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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 0.66696(4) 0.69778(5) 0.48807(3) 0.01944(13) Uani 1 1 d . . . . .
S1 S 0.49885(8) 0.41655(10) 0.36994(7) 0.0259(2) Uani 1 1 d . . . . .
S2 S 0.74451(8) 0.86172(11) 0.61400(7) 0.0291(3) Uani 1 1 d . . . . .
O1 O 0.7819(2) 0.7168(3) 0.58815(18) 0.0272(6) Uani 1 1 d . . . . .
O2 O 0.6472(2) 0.8824(3) 0.54655(18) 0.0264(6) Uani 1 1 d . . . . .
N1 N 0.5318(2) 0.7016(3) 0.4100(2) 0.0186(7) Uani 1 1 d . . . . .
N3 N 0.6891(2) 0.4954(3) 0.4731(2) 0.0181(7) Uani 1 1 d . . . . .
O3 O 0.7123(3) 0.8591(4) 0.7010(2) 0.0463(9) Uani 1 1 d . . . . .
N2 N 0.3874(2) 0.6464(3) 0.3200(2) 0.0207(7) Uani 1 1 d . . . . .
N4 N 0.6659(2) 0.2700(3) 0.4412(2) 0.0218(7) Uani 1 1 d . . . . .
O4 O 0.8271(2) 0.9668(3) 0.6034(2) 0.0452(9) Uani 1 1 d . . . . .
C5 C 0.6252(3) 0.4003(4) 0.4305(2) 0.0181(8) Uani 1 1 d . . . . .
C1 C 0.4764(3) 0.5981(4) 0.3682(2) 0.0170(8) Uani 1 1 d . . . . .
C2 C 0.4739(3) 0.8228(4) 0.3865(3) 0.0260(9) Uani 1 1 d . . . . .
H2 H 0.4933 0.9151 0.4063 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3030(3) 0.5623(4) 0.2708(3) 0.0274(9) Uani 1 1 d . . . . .
H4A H 0.3237 0.4626 0.2735 0.041 Uiso 1 1 calc R U . . .
H4B H 0.2939 0.5933 0.2096 0.041 Uiso 1 1 calc R U . . .
H4C H 0.2350 0.5747 0.2962 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7748(3) 0.4192(4) 0.5149(3) 0.0232(9) Uani 1 1 d . . . . .
H6 H 0.8339 0.4582 0.5513 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6191(3) 0.1411(4) 0.4006(3) 0.0314(10) Uani 1 1 d . . . . .
H8A H 0.5408 0.1415 0.4028 0.047 Uiso 1 1 calc R U . . .
H8B H 0.6507 0.0588 0.4323 0.047 Uiso 1 1 calc R U . . .
H8C H 0.6343 0.1367 0.3394 0.047 Uiso 1 1 calc R U . . .
C7 C 0.7609(3) 0.2808(4) 0.4957(3) 0.0271(9) Uani 1 1 d . . . . .
H7 H 0.8076 0.2058 0.5158 0.032 Uiso 1 1 calc R U . . .
C3 C 0.3859(3) 0.7903(4) 0.3314(3) 0.0289(9) Uani 1 1 d . . . . .
H3 H 0.3330 0.8542 0.3055 0.035 Uiso 1 1 calc R U . . .
S4 S 0.0000 0.4716(3) 0.2500 0.0886(9) Uani 1 2 d S TU P . .
C11 C 0.0720(6) 0.3533(7) 0.1919(4) 0.085(2) Uani 1 1 d . U . . .
H11A H 0.1114 0.4052 0.1504 0.128 Uiso 1 1 calc R U . . .
H11B H 0.0219 0.2871 0.1599 0.128 Uiso 1 1 calc R U . . .
H11C H 0.1233 0.3011 0.2328 0.128 Uiso 1 1 calc R U . . .
O6 O 0.0434(5) 0.5724(8) 0.2911(5) 0.0458(15) Uani 0.5 1 d . U P A -1
O5 O 0.7608(2) 0.7867(3) 0.3832(2) 0.0338(7) Uani 1 1 d . U . . .
S3A S 0.85421(11) 0.89545(16) 0.40297(12) 0.0318(5) Uani 0.687(4) 1 d . U P B 2
C9A C 0.9663(6) 0.8072(9) 0.4591(5) 0.0359(19) Uani 0.687(4) 1 d . U P B 2
H9A H 0.9490 0.7787 0.5172 0.054 Uiso 0.687(4) 1 calc R U P B 2
H9B H 1.0287 0.8706 0.4653 0.054 Uiso 0.687(4) 1 calc R U P B 2
H9C H 0.9833 0.7235 0.4259 0.054 Uiso 0.687(4) 1 calc R U P B 2
C10A C 0.9074(6) 0.9113(8) 0.3015(5) 0.0467(18) Uani 0.687(4) 1 d . U P B 2
H10A H 0.9227 0.8173 0.2796 0.070 Uiso 0.687(4) 1 calc R U P B 2
H10B H 0.9742 0.9666 0.3094 0.070 Uiso 0.687(4) 1 calc R U P B 2
H10C H 0.8547 0.9589 0.2594 0.070 Uiso 0.687(4) 1 calc R U P B 2
S3B S 0.8619(2) 0.8205(3) 0.34561(19) 0.0206(10) Uani 0.313(4) 1 d . U P B 3
C9B C 0.9603(15) 0.749(2) 0.4299(12) 0.036(3) Uani 0.313(4) 1 d . U P B 3
H9B1 H 0.9487 0.7897 0.4866 0.054 Uiso 0.313(4) 1 calc R U P B 3
H9B2 H 1.0332 0.7721 0.4163 0.054 Uiso 0.313(4) 1 calc R U P B 3
H9B3 H 0.9522 0.6463 0.4323 0.054 Uiso 0.313(4) 1 calc R U P B 3
C10B C 0.8833(10) 1.0008(14) 0.3717(9) 0.030(3) Uani 0.313(4) 1 d . U P B 3
H10D H 0.8350 1.0587 0.3318 0.045 Uiso 0.313(4) 1 calc R U P B 3
H10E H 0.9584 1.0257 0.3656 0.045 Uiso 0.313(4) 1 calc R U P B 3
H10F H 0.8685 1.0178 0.4320 0.045 Uiso 0.313(4) 1 calc R U P B 3
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'
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'
O O 0.0106 0.0060 '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 N1 93.95(13) . .
N3 Cu1 O1 94.65(12) . .
N1 Cu1 O1 165.65(12) . .
N3 Cu1 O2 160.00(12) . .
N1 Cu1 O2 96.85(12) . .
O1 Cu1 O2 71.73(11) . .
N3 Cu1 O5 101.05(12) . .
N1 Cu1 O5 91.97(12) . .
O1 Cu1 O5 97.62(11) . .
O2 Cu1 O5 95.36(12) . .
C1 S1 C5 103.26(17) . .
O3 S2 O4 113.0(2) . .
O3 S2 O1 110.66(19) . .
O4 S2 O1 110.45(18) . .
O3 S2 O2 110.65(18) . .
O4 S2 O2 110.87(18) . .
O1 S2 O2 100.56(15) . .
S2 O1 Cu1 93.96(13) . .
S2 O2 Cu1 93.73(13) . .
C1 N1 C2 105.0(3) . .
C1 N1 Cu1 130.6(3) . .
C2 N1 Cu1 124.3(3) . .
C5 N3 C6 105.4(3) . .
C5 N3 Cu1 129.8(2) . .
C6 N3 Cu1 124.6(3) . .
C1 N2 C3 106.9(3) . .
C1 N2 C4 127.0(3) . .
C3 N2 C4 126.0(3) . .
C5 N4 C7 107.2(3) . .
C5 N4 C8 126.2(3) . .
C7 N4 C8 126.7(3) . .
N3 C5 N4 111.6(3) . .
N3 C5 S1 131.3(3) . .
N4 C5 S1 117.0(3) . .
N1 C1 N2 111.6(3) . .
N1 C1 S1 130.5(3) . .
N2 C1 S1 117.8(3) . .
C3 C2 N1 109.9(3) . .
C3 C2 H2 125.1 . .
N1 C2 H2 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 . .
C7 C6 N3 109.3(3) . .
C7 C6 H6 125.3 . .
N3 C6 H6 125.3 . .
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 . .
C6 C7 N4 106.6(3) . .
C6 C7 H7 126.7 . .
N4 C7 H7 126.7 . .
C2 C3 N2 106.6(3) . .
C2 C3 H3 126.7 . .
N2 C3 H3 126.7 . .
O6 S4 C11 122.5(4) . .
O6 S4 C11 117.2(4) . 2
C11 S4 C11 99.9(6) . 2
S4 C11 H11A 109.5 . .
S4 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
S4 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
S3B O5 Cu1 153.0(2) . .
S3A O5 Cu1 122.82(18) . .
O5 S3A C10A 103.2(3) . .
O5 S3A C9A 108.3(3) . .
C10A S3A C9A 96.7(4) . .
S3A C9A H9A 109.5 . .
S3A C9A H9B 109.5 . .
H9A C9A H9B 109.5 . .
S3A C9A H9C 109.5 . .
H9A C9A H9C 109.5 . .
H9B C9A H9C 109.5 . .
S3A C10A H10A 109.5 . .
S3A C10A H10B 109.5 . .
H10A C10A H10B 109.5 . .
S3A C10A H10C 109.5 . .
H10A C10A H10C 109.5 . .
H10B C10A H10C 109.5 . .
O5 S3B C10B 103.6(5) . .
O5 S3B C9B 100.3(7) . .
C10B S3B C9B 97.3(8) . .
S3B C9B H9B1 109.5 . .
S3B C9B H9B2 109.5 . .
H9B1 C9B H9B2 109.5 . .
S3B C9B H9B3 109.5 . .
H9B1 C9B H9B3 109.5 . .
H9B2 C9B H9B3 109.5 . .
S3B C10B H10D 109.5 . .
S3B C10B H10E 109.5 . .
H10D C10B H10E 109.5 . .
S3B C10B H10F 109.5 . .
H10D C10B H10F 109.5 . .
H10E C10B H10F 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 1.957(3) .
Cu1 N1 1.959(3) .
Cu1 O1 1.992(3) .
Cu1 O2 1.997(3) .
Cu1 O5 2.259(3) .
S1 C1 1.744(4) .
S1 C5 1.746(4) .
S2 O3 1.439(3) .
S2 O4 1.455(3) .
S2 O1 1.518(3) .
S2 O2 1.519(3) .
N1 C1 1.326(5) .
N1 C2 1.385(5) .
N3 C5 1.328(5) .
N3 C6 1.388(5) .
N2 C1 1.345(5) .
N2 C3 1.377(5) .
N2 C4 1.463(5) .
N4 C5 1.339(5) .
N4 C7 1.378(5) .
N4 C8 1.465(5) .
C2 C3 1.346(5) .
C2 H2 0.9500 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C6 C7 1.353(6) .
C6 H6 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C7 H7 0.9500 .
C3 H3 0.9500 .
S4 O6 1.237(7) .
S4 C11 1.744(6) .
S4 C11 1.744(6) 2
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
O5 S3B 1.479(4) .
O5 S3A 1.561(3) .
S3A C10A 1.768(8) .
S3A C9A 1.770(7) .
C9A H9A 0.9800 .
C9A H9B 0.9800 .
C9A H9C 0.9800 .
C10A H10A 0.9800 .
C10A H10B 0.9800 .
C10A H10C 0.9800 .
S3B C10B 1.771(14) .
S3B C9B 1.815(18) .
C9B H9B1 0.9800 .
C9B H9B2 0.9800 .
C9B H9B3 0.9800 .
C10B H10D 0.9800 .
C10B H10E 0.9800 .
C10B H10F 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
C4 H4C O6 0.98 2.38 3.289(7) 153.5 .
C8 H8C O3 0.98 2.44 3.399(6) 167.3 4_565
C7 H7 O4 0.95 2.63 3.464(5) 146.1 1_545
C10A H10C O3 0.98 2.57 3.496(8) 158.1 4_575
C10A H10C O4 0.98 2.49 3.309(8) 141.2 4_575
C10B H10D O3 0.98 2.51 3.459(14) 162.4 4_575
