#------------------------------------------------------------------------------
#$Date: 2021-10-06 17:43:37 +0200 (Wed 06 de Oct de 2021) $
#$Revision: 269734 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/80/7708058.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_7708058
loop_
_publ_author_name
'DeLaney, Christopher'
'Sheng, Yan'
'Pectol, D. Chase'
'Vantansever, Erol'
'Zhang, Hanyuan'
'Bhuvanesh, Nattamai'
'Salas, Isaiah'
'Liu, Wenshe R.'
'Fierke, Carol F.'
'Darensbourg, Marcetta Y.'
_publ_section_title
;
 Zinc thiotropolone combinations as inhibitors of the SARS-CoV-2 main
 protease.
;
_journal_issue                   35
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12226
_journal_page_last               12233
_journal_paper_doi               10.1039/d1dt02499j
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C14 H10 O2 S2 Zn'
_chemical_formula_sum            'C14 H10 O2 S2 Zn'
_chemical_formula_weight         339.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-21 deposited with the CCDC.	2021-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.036(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5612(6)
_cell_length_b                   12.5681(10)
_cell_length_c                   13.8362(11)
_cell_measurement_reflns_used    9138
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      33.105
_cell_measurement_theta_min      2.990
_cell_volume                     1294.73(18)
_computing_cell_refinement
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_reduction
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22216
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.106
_diffrn_reflns_theta_min         2.990
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.211
_exptl_absorpt_correction_T_max  0.3399
_exptl_absorpt_correction_T_min  0.1826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1394 before and 0.0750 after correction. The Ratio of minimum to maximum transmission is 0.5372. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.507
_exptl_crystal_size_mid          0.342
_exptl_crystal_size_min          0.206
_refine_diff_density_max         1.444
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         2400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0499
_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)+(0.0609P)²+6.3255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2243
_reflns_number_total             2400
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt02499j2.cif
_cod_data_source_block           zn2merc
_cod_depositor_comments
'Adding full bibliography for 7708058--7708059.cif.'
_cod_database_code               7708058
_shelx_shelxl_version_number     2018/3
_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_max   0.659
_shelx_estimated_absorpt_t_min   0.400
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Zn1 Zn 0.500000 0.56608(3) 0.250000 0.01691(13) Uani 1 2 d S T P . .
S1 S 0.71426(8) 0.49740(5) 0.36887(5) 0.01799(15) Uani 1 1 d . . . . .
O1 O 0.4303(3) 0.66030(16) 0.35311(14) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.6665(3) 0.57830(19) 0.46296(17) 0.0154(4) Uani 1 1 d . . . . .
C2 C 0.5232(3) 0.65709(19) 0.43933(17) 0.0159(4) Uani 1 1 d . . . . .
C3 C 0.4794(4) 0.7354(2) 0.50591(19) 0.0197(4) Uani 1 1 d . . . . .
H3 H 0.390607 0.784845 0.477074 0.024 Uiso 1 1 calc R . . . .
C4 C 0.5417(4) 0.7528(2) 0.6039(2) 0.0250(5) Uani 1 1 d . . . . .
H4 H 0.485777 0.809804 0.632122 0.030 Uiso 1 1 calc R . . . .
C5 C 0.6752(4) 0.6990(3) 0.6684(2) 0.0271(6) Uani 1 1 d . . . . .
H5 H 0.699045 0.723219 0.734420 0.033 Uiso 1 1 calc R . . . .
C6 C 0.7753(4) 0.6143(3) 0.64511(19) 0.0263(6) Uani 1 1 d . . . . .
H6 H 0.860083 0.586932 0.698067 0.032 Uiso 1 1 calc R . . . .
C7 C 0.7711(4) 0.5624(2) 0.55521(19) 0.0208(5) Uani 1 1 d . . . . .
H7 H 0.855054 0.505813 0.557510 0.025 Uiso 1 1 calc R . . . .
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'
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'
Zn Zn 0.2839 1.4301 '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
_geom_angle_publ_flag
S1 Zn1 S1 135.27(4) 2_655 . ?
O1 Zn1 S1 87.23(6) 2_655 2_655 ?
O1 Zn1 S1 87.23(6) . . ?
O1 Zn1 S1 120.01(6) 2_655 . ?
O1 Zn1 S1 120.01(6) . 2_655 ?
O1 Zn1 O1 107.16(12) . 2_655 ?
C1 S1 Zn1 96.02(8) . . ?
C2 O1 Zn1 118.64(17) . . ?
C2 C1 S1 118.11(17) . . ?
C7 C1 S1 116.3(2) . . ?
C7 C1 C2 125.6(2) . . ?
O1 C2 C1 119.8(2) . . ?
O1 C2 C3 115.5(2) . . ?
C3 C2 C1 124.7(2) . . ?
C2 C3 H3 114.0 . . ?
C4 C3 C2 132.0(3) . . ?
C4 C3 H3 114.0 . . ?
C3 C4 H4 115.2 . . ?
C3 C4 C5 129.6(3) . . ?
C5 C4 H4 115.2 . . ?
C4 C5 H5 116.9 . . ?
C6 C5 C4 126.1(3) . . ?
C6 C5 H5 116.9 . . ?
C5 C6 H6 115.1 . . ?
C5 C6 C7 129.8(3) . . ?
C7 C6 H6 115.1 . . ?
C1 C7 C6 131.9(3) . . ?
C1 C7 H7 114.0 . . ?
C6 C7 H7 114.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 S1 2.2685(6) 2_655 ?
Zn1 S1 2.2685(6) . ?
Zn1 O1 1.9944(19) . ?
Zn1 O1 1.9944(19) 2_655 ?
S1 C1 1.739(3) . ?
O1 C2 1.275(3) . ?
C1 C2 1.462(3) . ?
C1 C7 1.394(3) . ?
C2 C3 1.426(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.400(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.400(4) . ?
C7 H7 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 S1 C1 C2 -0.94(18) . . . . ?
Zn1 S1 C1 C7 179.61(18) . . . . ?
Zn1 O1 C2 C1 -5.7(3) . . . . ?
Zn1 O1 C2 C3 172.65(17) . . . . ?
S1 C1 C2 O1 4.3(3) . . . . ?
S1 C1 C2 C3 -173.90(19) . . . . ?
S1 C1 C7 C6 177.2(3) . . . . ?
O1 C2 C3 C4 175.9(3) . . . . ?
C1 C2 C3 C4 -5.8(4) . . . . ?
C2 C1 C7 C6 -2.2(5) . . . . ?
C2 C3 C4 C5 2.5(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C5 C6 C7 C1 -0.6(5) . . . . ?
C7 C1 C2 O1 -176.3(2) . . . . ?
C7 C1 C2 C3 5.5(4) . . . . ?
