# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2332339'
_audit_update_record             
;
2024-10-29 deposited with the CCDC.	2024-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Br2 O2 S4 Zn'
_chemical_formula_weight         641.76

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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   17.3013(15)
_cell_length_b                   4.7563(4)
_cell_length_c                   26.838(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.010(4)
_cell_angle_gamma                90
_cell_volume                     2186.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14535
_cell_measurement_theta_min      2.643
_cell_measurement_theta_max      28.326
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.949
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    5.175
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Oxford Diffaction X-Calibor System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            14535
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_av_R_equivalents  0.1006
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.643
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2719
_reflns_number_gt                1867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  
'SHELXL-2016/6, PLATON, WINGX      (Ferrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+3.6030P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2719
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 -0.09244(15) 0.750000 0.01460(19) Uani 1 2 d S T P . .
O11 O 0.46889(16) 0.1472(6) 0.69168(11) 0.0153(7) Uani 1 1 d . . . . .
C12 C 0.5054(2) 0.1943(9) 0.65456(16) 0.0132(9) Uani 1 1 d . . . . .
C13 C 0.5763(2) 0.0652(9) 0.64617(17) 0.0155(10) Uani 1 1 d . . . . .
H13 H 0.596740 0.129184 0.617959 0.019 Uiso 1 1 calc R U . . .
C14 C 0.6198(2) -0.1406(9) 0.67335(16) 0.0135(9) Uani 1 1 d . . . . .
S15 S 0.60616(6) -0.3127(2) 0.72702(4) 0.0155(3) Uani 1 1 d . . . . .
S16 S 0.70055(6) -0.2400(3) 0.64404(4) 0.0201(3) Uani 1 1 d . . . . .
C17 C 0.7577(3) -0.4643(9) 0.68840(17) 0.0199(10) Uani 1 1 d . . . . .
H17A H 0.769699 -0.367866 0.719948 0.030 Uiso 1 1 calc R U . . .
H17B H 0.805277 -0.513308 0.675901 0.030 Uiso 1 1 calc R U . . .
H17C H 0.728729 -0.632087 0.693130 0.030 Uiso 1 1 calc R U . . .
C21 C 0.4689(2) 0.4047(9) 0.61722(16) 0.0118(9) Uani 1 1 d . . . . .
C22 C 0.3937(3) 0.4982(9) 0.62150(16) 0.0175(10) Uani 1 1 d . . . . .
H22 H 0.369446 0.434571 0.648200 0.021 Uiso 1 1 calc R U . . .
C23 C 0.3543(3) 0.6822(9) 0.58726(16) 0.0186(10) Uani 1 1 d . . . . .
H23 H 0.303824 0.739702 0.590398 0.022 Uiso 1 1 calc R U . . .
C24 C 0.3913(2) 0.7797(9) 0.54818(16) 0.0149(10) Uani 1 1 d . . . . .
C25 C 0.4669(2) 0.6984(9) 0.54412(16) 0.0163(10) Uani 1 1 d . . . . .
H25 H 0.492098 0.770367 0.518456 0.020 Uiso 1 1 calc R U . . .
C26 C 0.5048(3) 0.5107(9) 0.57821(16) 0.0163(10) Uani 1 1 d . . . . .
H26 H 0.555339 0.454141 0.574976 0.020 Uiso 1 1 calc R U . . .
Br24 Br 0.33837(3) 1.02581(10) 0.49948(2) 0.02283(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 O11 1.950(3) 2_656 ?
Zn1 O11 1.950(3) . ?
Zn1 S15 2.2732(11) . ?
Zn1 S15 2.2732(11) 2_656 ?
O11 C12 1.272(5) . ?
C12 C13 1.418(6) . ?
C12 C21 1.493(6) . ?
C13 C14 1.379(6) . ?
C13 H13 0.9300 . ?
C14 S15 1.702(4) . ?
C14 S16 1.761(4) . ?
S16 C17 1.790(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C21 C26 1.385(6) . ?
C21 C22 1.394(6) . ?
C22 C23 1.379(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.383(6) . ?
C24 Br24 1.893(4) . ?
C25 C26 1.377(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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
O11 Zn1 O11 108.48(18) 2_656 . ?
O11 Zn1 S15 110.12(8) 2_656 . ?
O11 Zn1 S15 101.23(9) . . ?
O11 Zn1 S15 101.23(9) 2_656 2_656 ?
O11 Zn1 S15 110.12(8) . 2_656 ?
S15 Zn1 S15 125.11(7) . 2_656 ?
C12 O11 Zn1 128.3(3) . . ?
O11 C12 C13 125.7(4) . . ?
O11 C12 C21 115.7(4) . . ?
C13 C12 C21 118.6(4) . . ?
C14 C13 C12 130.0(4) . . ?
C14 C13 H13 115.0 . . ?
C12 C13 H13 115.0 . . ?
C13 C14 S15 131.3(3) . . ?
C13 C14 S16 111.2(3) . . ?
S15 C14 S16 117.4(2) . . ?
C14 S15 Zn1 102.72(15) . . ?
C14 S16 C17 105.2(2) . . ?
S16 C17 H17A 109.5 . . ?
S16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 C21 C22 117.9(4) . . ?
C26 C21 C12 123.9(4) . . ?
C22 C21 C12 118.1(4) . . ?
C23 C22 C21 121.9(4) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 118.7(4) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C23 C24 C25 120.6(4) . . ?
C23 C24 Br24 120.0(3) . . ?
C25 C24 Br24 119.4(3) . . ?
C26 C25 C24 119.8(4) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C21 121.0(4) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?

_refine_diff_density_max         0.908
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.167

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2332340'
_audit_update_record             
;
2024-10-29 deposited with the CCDC.	2024-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 O4 S4 Zn'
_chemical_formula_weight         463.88

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'
Zn Zn 0.2839 1.4301 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   24.5268(14)
_cell_length_b                   4.7097(3)
_cell_length_c                   16.8095(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.665(3)
_cell_angle_gamma                90
_cell_volume                     1816.80(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13594
_cell_measurement_theta_min      3.551
_cell_measurement_theta_max      25.242

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.830
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.584
_exptl_absorpt_correction_T_max  0.710
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER D8 QUEST area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13594
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.551
_diffrn_reflns_theta_max         28.340
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2266
_reflns_number_gt                1979
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0249P)²+6.8237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2266
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.90791(9) 0.750000 0.02280(12) Uani 1 2 d S T P . .
O11 O 0.43214(7) 0.6652(4) 0.73373(10) 0.0219(4) Uani 1 1 d . . . . .
C12 C 0.38900(11) 0.6291(5) 0.66510(15) 0.0229(5) Uani 1 1 d . . . . .
C13 C 0.37801(12) 0.7693(6) 0.58649(15) 0.0287(6) Uani 1 1 d . . . . .
H13 H 0.343107 0.714710 0.542260 0.034 Uiso 1 1 calc R U . . .
C14 C 0.41064(13) 0.9741(6) 0.56458(16) 0.0325(6) Uani 1 1 d . . . . .
S15 S 0.47425(3) 1.13656(16) 0.62287(5) 0.03396(19) Uani 1 1 d . . . . .
S16A S 0.3699(7) 1.0563(18) 0.4551(3) 0.0353(15) Uani 0.60(3) 1 d . . P A 1
C17A C 0.4184(9) 1.300(3) 0.4308(8) 0.045(3) Uani 0.60(3) 1 d . . P A 1
H17A H 0.420524 1.477371 0.462343 0.067 Uiso 0.60(3) 1 calc R U P A 1
H17B H 0.403773 1.340158 0.369677 0.067 Uiso 0.60(3) 1 calc R U P A 1
H17C H 0.457351 1.215692 0.447239 0.067 Uiso 0.60(3) 1 calc R U P A 1
S16B S 0.3891(6) 1.1051(17) 0.4610(4) 0.0252(12) Uani 0.40(3) 1 d . . P A 2
C17B C 0.4403(8) 1.349(4) 0.4480(11) 0.030(3) Uani 0.40(3) 1 d . . P A 2
H17D H 0.440797 1.521295 0.481189 0.045 Uiso 0.40(3) 1 calc R U P A 2
H17E H 0.429263 1.399290 0.387800 0.045 Uiso 0.40(3) 1 calc R U P A 2
H17F H 0.479149 1.263045 0.467969 0.045 Uiso 0.40(3) 1 calc R U P A 2
C21 C 0.34735(10) 0.4175(6) 0.67082(16) 0.0253(5) Uani 1 1 d . . . B 2
C22 C 0.34825(11) 0.2509(6) 0.73692(17) 0.0267(5) Uani 1 1 d . . . B 2
H22 H 0.377379 0.246313 0.792052 0.032 Uiso 1 1 calc R U . B 2
C23 C 0.29660(13) 0.0842(7) 0.7069(2) 0.0407(8) Uani 1 1 d . . . B 2
H23 H 0.284292 -0.053512 0.738266 0.049 Uiso 1 1 calc R U . B 2
C24 C 0.26887(13) 0.1585(8) 0.6262(2) 0.0499(9) Uani 1 1 d . . . B 2
H24 H 0.233159 0.077533 0.590416 0.060 Uiso 1 1 calc R U . B 2
O25 O 0.29827(8) 0.3654(5) 0.60165(13) 0.0377(5) Uani 1 1 d . . . B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 O11 1.9571(17) . ?
Zn1 O11 1.9571(17) 2_656 ?
Zn1 S15 2.2744(7) 2_656 ?
Zn1 S15 2.2744(7) . ?
O11 C12 1.272(3) . ?
C12 C13 1.415(3) . ?
C12 C21 1.454(4) . ?
C13 C14 1.384(4) . ?
C13 H13 0.9500 . ?
C14 S15 1.703(3) . ?
C14 S16B 1.743(5) . ?
C14 S16A 1.799(5) . ?
S16A C17A 1.802(11) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
S16B C17B 1.772(15) . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C21 C22 1.354(4) . ?
C21 O25 1.369(3) . ?
C22 C23 1.423(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.332(5) . ?
C23 H23 0.9500 . ?
C24 O25 1.360(4) . ?
C24 H24 0.9500 . ?

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
O11 Zn1 O11 108.53(10) . 2_656 ?
O11 Zn1 S15 110.38(5) . 2_656 ?
O11 Zn1 S15 101.81(5) 2_656 2_656 ?
O11 Zn1 S15 101.82(5) . . ?
O11 Zn1 S15 110.38(5) 2_656 . ?
S15 Zn1 S15 123.48(5) 2_656 . ?
C12 O11 Zn1 126.80(17) . . ?
O11 C12 C13 127.4(3) . . ?
O11 C12 C21 114.2(2) . . ?
C13 C12 C21 118.3(2) . . ?
C14 C13 C12 129.5(3) . . ?
C14 C13 H13 115.2 . . ?
C12 C13 H13 115.2 . . ?
C13 C14 S15 131.2(2) . . ?
C13 C14 S16B 120.8(5) . . ?
S15 C14 S16B 108.0(5) . . ?
C13 C14 S16A 104.9(6) . . ?
S15 C14 S16A 123.9(6) . . ?
C14 S15 Zn1 102.83(10) . . ?
C14 S16A C17A 101.3(5) . . ?
S16A C17A H17A 109.5 . . ?
S16A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
S16A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C14 S16B C17B 112.0(6) . . ?
S16B C17B H17D 109.5 . . ?
S16B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
S16B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C22 C21 O25 110.3(2) . . ?
C22 C21 C12 130.0(2) . . ?
O25 C21 C12 119.6(2) . . ?
C21 C22 C23 105.9(3) . . ?
C21 C22 H22 127.1 . . ?
C23 C22 H22 127.1 . . ?
C24 C23 C22 106.7(3) . . ?
C24 C23 H23 126.7 . . ?
C22 C23 H23 126.7 . . ?
C23 C24 O25 111.2(3) . . ?
C23 C24 H24 124.4 . . ?
O25 C24 H24 124.4 . . ?
C24 O25 C21 105.8(2) . . ?

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
C17A H17B O11 0.98 2.61 3.450(11) 143.4 6_575
C17A H17C S15 0.98 2.89 3.695(12) 140.0 5_676
C17B H17E O11 0.98 2.63 3.538(17) 153.5 6_575
C17B H17F S15 0.98 2.90 3.580(17) 127.3 5_676

_refine_diff_density_max         1.369
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.085

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2332341'
_audit_update_record             
;
2024-10-29 deposited with the CCDC.	2024-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 F2 O2 S4 Zn'
_chemical_formula_weight         519.94

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   17.3481(16)
_cell_length_b                   51.429(5)
_cell_length_c                   4.7643(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4250.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16510
_cell_measurement_theta_min      2.833
_cell_measurement_theta_max      25.242

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER D8 QUEST area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16510
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -68
_diffrn_reflns_limit_k_max       68
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.833
_diffrn_reflns_theta_max         28.322
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2640
_reflns_number_gt                2574
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0116P)²+3.7793P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.025(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2640
_refine_ls_number_parameters     134
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0189
_refine_ls_wR_factor_ref         0.0455
_refine_ls_wR_factor_gt          0.0449
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.750000 0.250000 0.14284(7) 0.01821(9) Uani 1 2 d S T P . .
O11 O 0.76869(8) 0.28044(3) 0.3808(4) 0.0197(3) Uani 1 1 d . . . . .
C12 C 0.72389(12) 0.29956(4) 0.4276(5) 0.0173(4) Uani 1 1 d . . . . .
C13 C 0.65130(13) 0.30356(4) 0.3026(5) 0.0219(4) Uani 1 1 d . . . . .
H13 H 0.624596 0.318017 0.368255 0.026 Uiso 1 1 calc R U . . .
C14 C 0.61326(12) 0.28940(4) 0.0972(5) 0.0194(4) Uani 1 1 d . . . . .
S15 S 0.63942(3) 0.26199(2) -0.08013(12) 0.02013(11) Uani 1 1 d . . . . .
S16 S 0.52408(3) 0.30381(2) 0.01099(14) 0.02871(14) Uani 1 1 d . . . . .
C17 C 0.47635(14) 0.28069(5) -0.2118(6) 0.0285(5) Uani 1 1 d . . . . .
H17A H 0.504178 0.279086 -0.385080 0.043 Uiso 1 1 calc R U . . .
H17B H 0.424831 0.286528 -0.249648 0.043 Uiso 1 1 calc R U . . .
H17C H 0.474538 0.264100 -0.119654 0.043 Uiso 1 1 calc R U . . .
C21 C 0.75230(13) 0.31901(4) 0.6364(6) 0.0195(4) Uani 1 1 d . . . . .
C22 C 0.82324(13) 0.31490(4) 0.7659(5) 0.0246(5) Uani 1 1 d . . . . .
H22 H 0.851332 0.300021 0.723207 0.030 Uiso 1 1 calc R U . . .
C23 C 0.85263(15) 0.33255(5) 0.9568(6) 0.0305(6) Uani 1 1 d . . . . .
H23 H 0.900351 0.329810 1.040680 0.037 Uiso 1 1 calc R U . . .
C24 C 0.80975(16) 0.35423(5) 1.0199(6) 0.0326(6) Uani 1 1 d . . . . .
C25 C 0.73988(17) 0.35905(6) 0.9001(8) 0.0440(7) Uani 1 1 d . . . . .
H25 H 0.712101 0.373913 0.946199 0.053 Uiso 1 1 calc R U . . .
C26 C 0.71127(15) 0.34134(5) 0.7087(7) 0.0373(7) Uani 1 1 d . . . . .
H26 H 0.663531 0.344375 0.626114 0.045 Uiso 1 1 calc R U . . .
F27 F 0.83826(11) 0.37136(3) 1.2129(4) 0.0484(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 O11 1.9598(16) . ?
Zn1 O11 1.9599(16) 14_655 ?
Zn1 S15 2.2778(6) . ?
Zn1 S15 2.2778(6) 14_655 ?
O11 C12 1.273(2) . ?
C12 C13 1.408(3) . ?
C12 C21 1.494(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C14 S15 1.705(2) . ?
C14 S16 1.764(2) . ?
S16 C17 1.796(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C21 C22 1.393(3) . ?
C21 C26 1.394(3) . ?
C22 C23 1.382(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.362(4) . ?
C24 F27 1.366(3) . ?
C25 C26 1.381(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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
O11 Zn1 O11 109.32(10) . 14_655 ?
O11 Zn1 S15 101.12(5) . . ?
O11 Zn1 S15 110.28(5) 14_655 . ?
O11 Zn1 S15 110.28(5) . 14_655 ?
O11 Zn1 S15 101.12(5) 14_655 14_655 ?
S15 Zn1 S15 124.40(3) . 14_655 ?
C12 O11 Zn1 128.13(14) . . ?
O11 C12 C13 125.8(2) . . ?
O11 C12 C21 115.62(19) . . ?
C13 C12 C21 118.61(19) . . ?
C14 C13 C12 130.3(2) . . ?
C14 C13 H13 114.8 . . ?
C12 C13 H13 114.8 . . ?
C13 C14 S15 131.09(17) . . ?
C13 C14 S16 111.16(17) . . ?
S15 C14 S16 117.74(12) . . ?
C14 S15 Zn1 102.52(7) . . ?
C14 S16 C17 105.30(11) . . ?
S16 C17 H17A 109.5 . . ?
S16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C21 C26 117.8(2) . . ?
C22 C21 C12 119.00(19) . . ?
C26 C21 C12 123.2(2) . . ?
C23 C22 C21 121.2(2) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 118.5(2) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C25 C24 F27 119.1(3) . . ?
C25 C24 C23 122.5(2) . . ?
F27 C24 C23 118.3(3) . . ?
C24 C25 C26 118.4(2) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C25 C26 C21 121.5(2) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.042

