# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_IIB
_database_code_depnum_ccdc_archive 'CCDC 2065142'
loop_
_audit_author_name
_audit_author_address
'Jozef Kozisek'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2021-02-25 deposited with the CCDC.	2021-04-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 O S2'
_chemical_formula_sum            'C24 H22 O S2'
_chemical_formula_weight         390.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   41.2198(6)
_cell_length_b                   5.82020(10)
_cell_length_c                   8.0162(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.9880(10)
_cell_angle_gamma                90
_cell_volume                     1922.86(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    56134
_cell_measurement_temperature    100
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      72.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.583

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_absorpt_correction_T_min  0.1050
_exptl_absorpt_correction_T_max  0.1630

_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             824
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.090
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            33369
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.897
_diffrn_reflns_theta_min         3.217
_diffrn_ambient_temperature      100


_diffrn_detector                 HPAD
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris 300K Pilatus3R'
_diffrn_measurement_details      
;
 1615 frames, detector distance = 40 mm
;
_diffrn_measurement_device       '4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_target            Cu
_diffrn_source_type              'Xenocs Cu tube'
_diffrn_source_voltage           50
_reflns_d_resolution_high        0.811
_reflns_d_resolution_low         13.320


_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.937

_reflns_number_gt                3392
_reflns_number_total             3522
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'



_refine_diff_density_max         0.348
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00150(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+1.1706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0788
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
C1 C 0.65328(3) 0.5981(3) 0.87159(18) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.63249(3) 0.4492(3) 0.98071(19) 0.0265(3) Uani 1 1 d . . . . .
H2A H 0.643578 0.426122 1.087113 0.032 Uiso 1 1 calc R . . . .
H2B H 0.629756 0.300085 0.928366 0.032 Uiso 1 1 calc R . . . .
C3 C 0.59925(3) 0.5529(3) 1.0112(2) 0.0328(4) Uani 1 1 d . . . . .
H3A H 0.586455 0.545191 0.908621 0.039 Uiso 1 1 calc R . . . .
H3B H 0.601877 0.713674 1.040192 0.039 Uiso 1 1 calc R . . . .
C4 C 0.58082(4) 0.4325(4) 1.1493(2) 0.0378(4) Uani 1 1 d . . . . .
H4A H 0.578614 0.270987 1.121656 0.045 Uiso 1 1 calc R . . . .
H4B H 0.593338 0.443536 1.252579 0.045 Uiso 1 1 calc R . . . .
C5 C 0.54730(4) 0.5336(4) 1.1761(2) 0.0475(5) Uani 1 1 d . . . . .
H5A H 0.534120 0.510425 1.076069 0.057 Uiso 1 1 calc R . . . .
H5B H 0.549307 0.697812 1.194240 0.057 Uiso 1 1 calc R . . . .
C6 C 0.53027(5) 0.4260(6) 1.3241(3) 0.0745(8) Uani 1 1 d . . . . .
H6A H 0.528697 0.262893 1.308069 0.112 Uiso 1 1 calc GR . . . .
H6B H 0.508898 0.489958 1.332842 0.112 Uiso 1 1 calc GR . . . .
H6C H 0.542479 0.457358 1.424569 0.112 Uiso 1 1 calc GR . . . .
C7 C 0.68375(3) 0.5020(3) 0.80800(17) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.69841(3) 0.2930(3) 0.83020(18) 0.0204(3) Uani 1 1 d . . . . .
H8 H 0.689176 0.172283 0.888720 0.025 Uiso 1 1 calc R . . . .
C9 C 0.72909(3) 0.2804(2) 0.75458(17) 0.0193(3) Uani 1 1 d . . . . .
H9 H 0.742273 0.150781 0.758776 0.023 Uiso 1 1 calc R . . . .
C10 C 0.73737(3) 0.4800(2) 0.67424(16) 0.0169(3) Uani 1 1 d . . . . .
C11 C 0.76671(3) 0.5382(2) 0.58610(16) 0.0166(3) Uani 1 1 d . . . . .
C12 C 0.77378(3) 0.7409(3) 0.50767(17) 0.0190(3) Uani 1 1 d . . . . .
H12 H 0.759409 0.863849 0.500810 0.023 Uiso 1 1 calc R . . . .
C13 C 0.80495(3) 0.7445(3) 0.43845(17) 0.0185(3) Uani 1 1 d . . . . .
H13 H 0.813137 0.870186 0.381168 0.022 Uiso 1 1 calc R . . . .
C14 C 0.82205(3) 0.5455(2) 0.46351(16) 0.0157(3) Uani 1 1 d . . . . .
C15 C 0.85511(3) 0.4908(2) 0.41166(16) 0.0149(3) Uani 1 1 d . . . . .
C16 C 0.87279(3) 0.6443(2) 0.31776(16) 0.0154(3) Uani 1 1 d . . . . .
H16 H 0.863175 0.781392 0.283689 0.019 Uiso 1 1 calc R . . . .
C17 C 0.92374(3) 0.7552(2) 0.17801(16) 0.0163(3) Uani 1 1 d . . . . .
H17 H 0.914614 0.894406 0.144916 0.020 Uiso 1 1 calc R . . . .
C18 C 0.95499(3) 0.7041(2) 0.13530(17) 0.0180(3) Uani 1 1 d . . . . .
H18 H 0.966846 0.808587 0.073164 0.022 Uiso 1 1 calc R . . . .
C19 C 0.96929(3) 0.4940(2) 0.18505(16) 0.0184(3) Uani 1 1 d . . . . .
H19 H 0.990483 0.460523 0.155454 0.022 Uiso 1 1 calc R . . . .
C20 C 0.95200(3) 0.3394(2) 0.27679(16) 0.0172(3) Uani 1 1 d . . . . .
H20 H 0.961662 0.201894 0.309572 0.021 Uiso 1 1 calc R . . . .
C21 C 0.90107(3) 0.2295(2) 0.41657(16) 0.0156(3) Uani 1 1 d . . . . .
H21 H 0.910198 0.090074 0.449138 0.019 Uiso 1 1 calc R . . . .
C22 C 0.86999(3) 0.2798(2) 0.46029(16) 0.0162(3) Uani 1 1 d . . . . .
H22 H 0.858350 0.174603 0.522842 0.019 Uiso 1 1 calc R . . . .
C23 C 0.90515(3) 0.5976(2) 0.27232(16) 0.0147(3) Uani 1 1 d . . . . .
C24 C 0.91962(3) 0.3862(2) 0.32242(16) 0.0146(3) Uani 1 1 d . . . . .
O1 O 0.64637(3) 0.7976(2) 0.83951(15) 0.0317(3) Uani 1 1 d . . . . .
S1 S 0.70736(2) 0.68503(6) 0.69157(4) 0.01975(11) Uani 1 1 d . . . . .
S2 S 0.79901(2) 0.34940(6) 0.57452(4) 0.01707(11) 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
C1 C2 1.508(2) . ?
C1 C7 1.4738(18) . ?
C1 O1 1.2221(19) . ?
C2 C3 1.521(2) . ?
C3 C4 1.524(2) . ?
C4 C5 1.520(2) . ?
C5 C6 1.524(3) . ?
C7 C8 1.368(2) . ?
C7 S1 1.7274(14) . ?
C8 C9 1.4139(19) . ?
C9 C10 1.374(2) . ?
C10 C11 1.4513(18) . ?
C10 S1 1.7260(13) . ?
C11 C12 1.370(2) . ?
C11 S2 1.7303(13) . ?
C12 C13 1.4087(18) . ?
C13 C14 1.3691(19) . ?
C14 C15 1.4665(17) . ?
C14 S2 1.7394(13) . ?
C15 C16 1.3836(19) . ?
C15 C22 1.4238(19) . ?
C16 C23 1.4150(18) . ?
C17 C18 1.3710(19) . ?
C17 C23 1.4213(18) . ?
C18 C19 1.412(2) . ?
C19 C20 1.3695(19) . ?
C20 C24 1.4164(18) . ?
C21 C22 1.3659(18) . ?
C21 C24 1.4165(18) . ?
C23 C24 1.4223(19) . ?

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
C7 C1 C2 118.61(13) . . ?
O1 C1 C2 122.36(13) . . ?
O1 C1 C7 118.97(13) . . ?
C1 C2 C3 112.81(13) . . ?
C2 C3 C4 113.34(14) . . ?
C5 C4 C3 112.97(16) . . ?
C4 C5 C6 112.51(18) . . ?
C1 C7 S1 116.39(11) . . ?
C8 C7 C1 132.00(13) . . ?
C8 C7 S1 111.52(10) . . ?
C7 C8 C9 112.74(13) . . ?
C10 C9 C8 112.84(13) . . ?
C9 C10 C11 129.89(13) . . ?
C9 C10 S1 111.26(10) . . ?
C11 C10 S1 118.82(11) . . ?
C10 C11 S2 121.75(11) . . ?
C12 C11 C10 127.59(12) . . ?
C12 C11 S2 110.62(10) . . ?
C11 C12 C13 113.35(12) . . ?
C14 C13 C12 113.60(13) . . ?
C13 C14 C15 128.37(12) . . ?
C13 C14 S2 110.24(10) . . ?
C15 C14 S2 121.39(10) . . ?
C16 C15 C14 120.98(12) . . ?
C16 C15 C22 118.51(12) . . ?
C22 C15 C14 120.49(12) . . ?
C15 C16 C23 121.59(12) . . ?
C18 C17 C23 120.69(13) . . ?
C17 C18 C19 120.43(13) . . ?
C20 C19 C18 120.14(12) . . ?
C19 C20 C24 120.90(13) . . ?
C22 C21 C24 121.07(12) . . ?
C21 C22 C15 121.07(12) . . ?
C16 C23 C17 122.17(12) . . ?
C16 C23 C24 119.08(12) . . ?
C17 C23 C24 118.75(12) . . ?
C20 C24 C21 122.26(12) . . ?
C20 C24 C23 119.07(12) . . ?
C21 C24 C23 118.67(11) . . ?
C10 S1 C7 91.63(7) . . ?
C11 S2 C14 92.19(6) . . ?

####################################################################### 
# 
# 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_IIC
_database_code_depnum_ccdc_archive 'CCDC 2065143'
loop_
_audit_author_name
_audit_author_address
'Jozef Kozisek'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2021-02-25 deposited with the CCDC.	2021-04-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_IIC                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01541 Ang.
RESPONSE: High R-value due to low quality of the crystal
;
_vrf_PLAT930_IIC                 
;
PROBLEM: FCF-based   Twin Law ( 1 0 0)[ 4 0 1] Est.d BASF       0.10 Check
RESPONSE: Data of crystal structure IIC was integrated up to four orientation matrices. No improvement. Single crystal consists of small domains shifted in one direction.
;
# Added during the CSD deposition process: Thursday 25 February 2021 09:57 AM
# end Validation Reply Form

_audit_creation_date             2021-02-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H11 F15 O S2'
_chemical_formula_sum            'C26 H11 F15 O S2'
_chemical_formula_weight         688.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   29.2832(8)
_cell_length_b                   5.93510(10)
_cell_length_c                   14.6720(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.692(2)
_cell_angle_gamma                90
_cell_volume                     2527.03(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    72452
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.50
_cell_measurement_theta_min      3.05
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.175

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_absorpt_correction_T_min  0.0503
_exptl_absorpt_correction_T_max  0.3355

_exptl_crystal_density_diffrn    1.810
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1368
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            83979
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        65.090
_diffrn_reflns_theta_max         65.090
_diffrn_reflns_theta_min         3.046
_diffrn_ambient_temperature      100


_diffrn_detector                 HPAD
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris 300K Pilatus3R'
_diffrn_measurement_details      
;
 1615 frames, detector distance = 40 mm
;
_diffrn_measurement_device       '4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_target            Cu
_diffrn_source_type              'Xenocs Cu tube'
_diffrn_source_voltage           50
_reflns_d_resolution_high        0.811
_reflns_d_resolution_low         13.320




_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996

_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3533
_reflns_number_total             4270
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'

_refine_diff_density_max         0.957
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.140
_refine_ls_extinction_coef       0.00082(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.1209
_refine_ls_restrained_S_all      1.092
_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)+(0.0693P)²+43.4537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2959
_refine_ls_wR_factor_ref         0.3036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S1 S 0.66814(9) 0.7377(4) 0.14343(16) 0.0461(7) Uani 1 1 d . . . . .
S2 S 0.55939(9) 0.8539(4) 0.12855(16) 0.0451(7) Uani 1 1 d . . . . .
F1 F 0.8240(2) 0.8914(11) 0.2032(4) 0.0602(16) Uani 1 1 d . . . . .
F2 F 0.8375(2) 0.5458(11) 0.1619(4) 0.0601(17) Uani 1 1 d . . . . .
F3 F 0.7878(2) 0.4231(11) 0.3188(4) 0.0573(16) Uani 1 1 d . . . . .
F4 F 0.8051(2) 0.7679(10) 0.3635(4) 0.0527(15) Uani 1 1 d . . . . .
F5 F 0.8732(2) 0.3151(11) 0.3129(4) 0.0632(17) Uani 1 1 d . . . . .
F6 F 0.8964(2) 0.6669(12) 0.3233(4) 0.0605(16) Uani 1 1 d . . . . .
F7 F 0.8370(2) 0.4015(12) 0.4835(4) 0.0601(17) Uani 1 1 d . . . . .
F8 F 0.8805(2) 0.7001(10) 0.4928(4) 0.0602(16) Uani 1 1 d . . . . .
F9 F 0.9047(2) 0.1296(10) 0.4794(4) 0.0665(18) Uani 1 1 d . . . . .
F10 F 0.9511(2) 0.3915(13) 0.4421(5) 0.0677(18) Uani 1 1 d . . . . .
F11 F 0.8993(2) 0.4054(12) 0.6423(4) 0.0646(18) Uani 1 1 d . . . . .
F12 F 0.9594(2) 0.5752(11) 0.6024(5) 0.0664(18) Uani 1 1 d . . . . .
F13 F 0.9409(3) 0.0090(12) 0.6526(5) 0.075(2) Uani 1 1 d . . . . .
F14 F 0.9985(3) 0.1431(13) 0.5894(5) 0.076(2) Uani 1 1 d . . . . .
F15 F 0.9860(3) 0.2620(12) 0.7231(5) 0.074(2) Uani 1 1 d . . . . .
O1 O 0.7510(3) 0.4769(13) 0.1147(5) 0.059(2) Uani 1 1 d . . . . .
C1 C 0.7243(4) 0.8027(19) 0.1811(7) 0.050(3) Uani 1 1 d . . . . .
C2 C 0.7282(4) 1.0077(17) 0.2258(7) 0.048(2) Uani 1 1 d . . . . .
H2 H 0.756063 1.069543 0.251927 0.058 Uiso 1 1 calc R . . . .
C3 C 0.6855(4) 1.1120(19) 0.2276(7) 0.052(3) Uani 1 1 d . . . . .
H3 H 0.682076 1.251921 0.254412 0.062 Uiso 1 1 calc R . . . .
C4 C 0.6490(4) 0.9869(17) 0.1857(6) 0.044(2) Uani 1 1 d . . . . .
C5 C 0.6013(4) 1.0406(17) 0.1762(6) 0.047(2) Uani 1 1 d . . . . .
C6 C 0.5802(4) 1.2377(16) 0.2008(6) 0.043(2) Uani 1 1 d . . . . .
H6 H 0.596514 1.358868 0.229045 0.051 Uiso 1 1 calc R . . . .
C7 C 0.5331(4) 1.2371(16) 0.1798(6) 0.044(2) Uani 1 1 d . . . . .
H7 H 0.514874 1.359407 0.191493 0.053 Uiso 1 1 calc R . . . .
C8 C 0.5148(4) 1.0392(16) 0.1395(6) 0.044(2) Uani 1 1 d . . . . .
C9 C 0.7594(4) 0.6439(18) 0.1637(7) 0.049(2) Uani 1 1 d . . . . .
C10 C 0.8099(4) 0.6724(19) 0.2071(7) 0.053(3) Uani 1 1 d . . . . .
C11 C 0.8171(4) 0.5943(18) 0.3114(7) 0.048(2) Uani 1 1 d . . . . .
C12 C 0.8656(4) 0.5202(19) 0.3484(7) 0.050(3) Uani 1 1 d . . . . .
C13 C 0.8749(4) 0.4920(19) 0.4568(7) 0.051(3) Uani 1 1 d . . . . .
C14 C 0.9159(4) 0.3487(18) 0.4921(7) 0.051(3) Uani 1 1 d . . . . .
C15 C 0.9351(4) 0.3835(19) 0.5948(8) 0.055(3) Uani 1 1 d . . . . .
C16 C 0.9656(5) 0.193(2) 0.6365(9) 0.067(3) Uani 1 1 d . . . . .
C17 C 0.4668(3) 0.9770(16) 0.1086(6) 0.041(2) Uani 1 1 d . . . . .
C18 C 0.4305(4) 1.1221(17) 0.1221(6) 0.045(2) Uani 1 1 d . . . . .
H18 H 0.437304 1.260173 0.150712 0.054 Uiso 1 1 calc R . . . .
C19 C 0.3480(4) 1.2136(18) 0.1064(6) 0.045(2) Uani 1 1 d . . . . .
H19 H 0.354286 1.353617 0.133656 0.054 Uiso 1 1 calc R . . . .
C20 C 0.3040(4) 1.154(2) 0.0793(7) 0.054(3) Uani 1 1 d . . . . .
H20 H 0.280356 1.252778 0.088835 0.065 Uiso 1 1 calc R . . . .
C21 C 0.2931(4) 0.9420(17) 0.0362(7) 0.049(2) Uani 1 1 d . . . . .
H21 H 0.262622 0.903129 0.016611 0.059 Uiso 1 1 calc R . . . .
C22 C 0.3279(4) 0.7961(19) 0.0238(7) 0.050(3) Uani 1 1 d . . . . .
H22 H 0.320711 0.656312 -0.002971 0.060 Uiso 1 1 calc R . . . .
C23 C 0.4112(4) 0.7114(16) 0.0380(6) 0.047(2) Uani 1 1 d . . . . .
H23 H 0.404670 0.572584 0.009877 0.056 Uiso 1 1 calc R . . . .
C24 C 0.4557(4) 0.7651(17) 0.0646(7) 0.045(2) Uani 1 1 d . . . . .
H24 H 0.478988 0.665356 0.054462 0.055 Uiso 1 1 calc R . . . .
C25 C 0.3855(4) 1.0667(17) 0.0943(6) 0.043(2) Uani 1 1 d . . . . .
C26 C 0.3742(4) 0.8529(18) 0.0504(6) 0.046(2) 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
S1 C1 1.708(11) . ?
S1 C4 1.725(10) . ?
S2 C5 1.730(10) . ?
S2 C8 1.732(10) . ?
F1 C10 1.367(12) . ?
F2 C10 1.341(12) . ?
F3 C11 1.343(11) . ?
F4 C11 1.356(11) . ?
F5 C12 1.354(12) . ?
F6 C12 1.341(12) . ?
F7 C13 1.336(12) . ?
F8 C13 1.344(12) . ?
F9 C14 1.348(12) . ?
F10 C14 1.368(12) . ?
F11 C15 1.339(13) . ?
F12 C15 1.339(13) . ?
F13 C16 1.349(15) . ?
F14 C16 1.294(14) . ?
F15 C16 1.390(14) . ?
O1 C9 1.229(13) . ?
C1 C2 1.380(15) . ?
C1 C9 1.441(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(15) . ?
C4 C5 1.423(14) . ?
C5 C6 1.393(14) . ?
C6 H6 0.9300 . ?
C6 C7 1.372(14) . ?
C7 H7 0.9300 . ?
C7 C8 1.390(14) . ?
C8 C17 1.465(14) . ?
C9 C10 1.541(15) . ?
C10 C11 1.586(14) . ?
C11 C12 1.516(15) . ?
C12 C13 1.586(15) . ?
C13 C14 1.506(15) . ?
C14 C15 1.549(15) . ?
C15 C16 1.517(16) . ?
C17 C18 1.401(14) . ?
C17 C24 1.431(14) . ?
C18 H18 0.9300 . ?
C18 C25 1.368(14) . ?
C19 H19 0.9300 . ?
C19 C20 1.344(15) . ?
C19 C25 1.431(14) . ?
C20 H20 0.9300 . ?
C20 C21 1.427(15) . ?
C21 H21 0.9300 . ?
C21 C22 1.368(15) . ?
C22 H22 0.9300 . ?
C22 C26 1.399(14) . ?
C23 H23 0.9300 . ?
C23 C24 1.347(14) . ?
C23 C26 1.403(14) . ?
C24 H24 0.9300 . ?
C25 C26 1.441(14) . ?

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
C1 S1 C4 92.0(5) . . ?
C5 S2 C8 93.4(5) . . ?
C2 C1 S1 111.5(8) . . ?
C2 C1 C9 130.2(10) . . ?
C9 C1 S1 118.3(9) . . ?
C1 C2 H2 123.7 . . ?
C1 C2 C3 112.5(10) . . ?
C3 C2 H2 123.7 . . ?
C2 C3 H3 123.4 . . ?
C4 C3 C2 113.2(10) . . ?
C4 C3 H3 123.4 . . ?
C3 C4 S1 110.7(8) . . ?
C3 C4 C5 128.0(10) . . ?
C5 C4 S1 121.2(8) . . ?
C4 C5 S2 122.0(8) . . ?
C6 C5 S2 109.1(8) . . ?
C6 C5 C4 128.9(9) . . ?
C5 C6 H6 123.0 . . ?
C7 C6 C5 114.1(9) . . ?
C7 C6 H6 123.0 . . ?
C6 C7 H7 122.7 . . ?
C6 C7 C8 114.6(9) . . ?
C8 C7 H7 122.7 . . ?
C7 C8 S2 108.9(8) . . ?
C7 C8 C17 130.1(9) . . ?
C17 C8 S2 121.0(7) . . ?
O1 C9 C1 122.6(10) . . ?
O1 C9 C10 115.8(10) . . ?
C1 C9 C10 121.5(10) . . ?
F1 C10 C9 111.4(9) . . ?
F1 C10 C11 108.5(8) . . ?
F2 C10 F1 107.9(8) . . ?
F2 C10 C9 110.0(9) . . ?
F2 C10 C11 107.7(9) . . ?
C9 C10 C11 111.2(8) . . ?
F3 C11 F4 108.3(8) . . ?
F3 C11 C10 107.2(8) . . ?
F3 C11 C12 109.2(9) . . ?
F4 C11 C10 108.2(9) . . ?
F4 C11 C12 108.5(8) . . ?
C12 C11 C10 115.3(8) . . ?
F5 C12 C11 108.5(8) . . ?
F5 C12 C13 106.0(9) . . ?
F6 C12 F5 109.1(8) . . ?
F6 C12 C11 110.2(9) . . ?
F6 C12 C13 108.2(8) . . ?
C11 C12 C13 114.7(8) . . ?
F7 C13 F8 108.5(9) . . ?
F7 C13 C12 107.3(8) . . ?
F7 C13 C14 109.1(9) . . ?
F8 C13 C12 107.0(9) . . ?
F8 C13 C14 109.5(9) . . ?
C14 C13 C12 115.3(9) . . ?
F9 C14 F10 106.9(9) . . ?
F9 C14 C13 109.2(9) . . ?
F9 C14 C15 108.3(8) . . ?
F10 C14 C13 109.5(9) . . ?
F10 C14 C15 107.2(9) . . ?
C13 C14 C15 115.4(9) . . ?
F11 C15 C14 108.2(9) . . ?
F11 C15 C16 108.7(10) . . ?
F12 C15 F11 108.5(9) . . ?
F12 C15 C14 108.3(9) . . ?
F12 C15 C16 108.7(10) . . ?
C16 C15 C14 114.3(10) . . ?
F13 C16 F15 104.6(10) . . ?
F13 C16 C15 111.9(11) . . ?
F14 C16 F13 111.2(11) . . ?
F14 C16 F15 107.3(11) . . ?
F14 C16 C15 113.3(10) . . ?
F15 C16 C15 108.0(10) . . ?
C18 C17 C8 121.0(9) . . ?
C18 C17 C24 118.3(9) . . ?
C24 C17 C8 120.7(9) . . ?
C17 C18 H18 119.0 . . ?
C25 C18 C17 121.9(10) . . ?
C25 C18 H18 119.0 . . ?
C20 C19 H19 119.2 . . ?
C20 C19 C25 121.7(10) . . ?
C25 C19 H19 119.2 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.7(11) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.5(11) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C26 121.4(11) . . ?
C26 C22 H22 119.3 . . ?
C24 C23 H23 118.1 . . ?
C24 C23 C26 123.8(10) . . ?
C26 C23 H23 118.1 . . ?
C17 C24 H24 120.3 . . ?
C23 C24 C17 119.4(9) . . ?
C23 C24 H24 120.3 . . ?
C18 C25 C19 122.8(10) . . ?
C18 C25 C26 120.0(9) . . ?
C19 C25 C26 117.3(9) . . ?
C22 C26 C23 123.8(10) . . ?
C22 C26 C25 119.5(10) . . ?
C23 C26 C25 116.7(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
