# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_uch066_CF3C5F5_before
_audit_block_doi                 10.5517/ccdc.csd.cc28b51v
_database_code_depnum_ccdc_archive 'CCDC 2095136'
loop_
_audit_author_name
_audit_author_address
'yuma nakagawa'
;Ryukoku University
Japan
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H16 F8 N2 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         572.53

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9257(3)
_cell_length_b                   28.2706(15)
_cell_length_c                   12.4537(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.8416(17)
_cell_angle_gamma                90
_cell_volume                     2402.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    391
_cell_measurement_theta_min      3.0493
_cell_measurement_theta_max      21.9077
_cell_measurement_temperature    128.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.064
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160

_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      128.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            17388
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             4211
_reflns_number_gt                3316
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1150
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_number_reflns         4211
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+0.6664P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.352
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0171 0.0103 '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'

_computing_data_collection       ?
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5522(4) 0.62285(10) 0.4294(2) 0.0317(6) Uani d . . . 1.0 . .
H H1A 0.5445 0.6565 0.4469 0.048 Uiso calc U . R 1.0 . .
H H1B 0.4659 0.6048 0.4689 0.048 Uiso calc U . R 1.0 . .
H H1C 0.511 0.6182 0.3509 0.048 Uiso calc U . R 1.0 . .
C C2 0.7586(4) 0.60604(9) 0.4623(2) 0.0252(6) Uani d . . . 1.0 . .
C C3 0.9039(3) 0.59954(9) 0.4013(2) 0.0233(6) Uani d . . . 1.0 . .
C C4 1.0682(3) 0.57261(9) 0.5575(2) 0.0234(6) Uani d . . . 1.0 . .
C C5 1.2266(3) 0.55263(9) 0.6377(2) 0.0223(5) Uani d . . . 1.0 . .
C C6 1.3548(4) 0.51989(9) 0.6043(2) 0.0286(6) Uani d . . . 1.0 . .
H H6 1.3396 0.511 0.5298 0.034 Uiso calc U . R 1.0 . .
C C7 1.5044(4) 0.50030(10) 0.6794(2) 0.0332(6) Uani d . . . 1.0 . .
H H7 1.5918 0.4781 0.6564 0.04 Uiso calc U . R 1.0 . .
C C8 1.5260(4) 0.51316(10) 0.7876(2) 0.0337(7) Uani d . . . 1.0 . .
H H8 1.6286 0.4998 0.839 0.04 Uiso calc U . R 1.0 . .
C C9 1.3992(4) 0.54537(10) 0.8217(2) 0.0315(6) Uani d . . . 1.0 . .
H H9 1.4148 0.554 0.8964 0.038 Uiso calc U . R 1.0 . .
C C10 1.2499(4) 0.56506(9) 0.7476(2) 0.0281(6) Uani d . . . 1.0 . .
H H10 1.1628 0.5871 0.7714 0.034 Uiso calc U . R 1.0 . .
C C11 1.0086(4) 0.71071(11) 0.4133(2) 0.0390(7) Uani d . . . 1.0 . .
H H11A 0.9958 0.6959 0.4829 0.059 Uiso calc U . R 1.0 . .
H H11B 1.0706 0.7418 0.4271 0.059 Uiso calc U . R 1.0 . .
H H11C 1.0897 0.6907 0.3746 0.059 Uiso calc U . R 1.0 . .
C C12 0.8078(4) 0.71657(9) 0.3446(2) 0.0282(6) Uani d . . . 1.0 . .
C C13 0.7106(3) 0.68858(9) 0.26404(19) 0.0247(6) Uani d . . . 1.0 . .
C C14 0.4852(4) 0.74438(9) 0.25759(19) 0.0247(6) Uani d . . . 1.0 . .
C C15 0.2989(4) 0.77001(9) 0.22602(19) 0.0250(6) Uani d . . . 1.0 . .
C C16 0.1535(4) 0.75131(10) 0.1474(2) 0.0329(7) Uani d . . . 1.0 . .
H H16 0.1754 0.7223 0.113 0.039 Uiso calc U . R 1.0 . .
C C17 -0.0233(4) 0.77451(10) 0.1186(2) 0.0393(7) Uani d . . . 1.0 . .
H H17 -0.1218 0.7615 0.0642 0.047 Uiso calc U . R 1.0 . .
C C18 -0.0575(4) 0.81672(10) 0.1689(2) 0.0360(7) Uani d . . . 1.0 . .
H H18 -0.1792 0.8327 0.1492 0.043 Uiso calc U . R 1.0 . .
C C19 0.0860(4) 0.83533(10) 0.2476(3) 0.0409(7) Uani d . . . 1.0 . .
H H19 0.0633 0.8642 0.2824 0.049 Uiso calc U . R 1.0 . .
C C20 0.2634(4) 0.81220(10) 0.2762(2) 0.0362(7) Uani d . . . 1.0 . .
H H20 0.3617 0.8253 0.3306 0.043 Uiso calc U . R 1.0 . .
C C21 0.8853(3) 0.60922(9) 0.2846(2) 0.0246(6) Uani d . . . 1.0 . .
C C22 0.9835(3) 0.57794(9) 0.2131(2) 0.0265(6) Uani d . . . 1.0 . .
C C24 0.7675(4) 0.63485(10) 0.1058(2) 0.0298(6) Uani d . . . 1.0 . .
C C25 0.7856(3) 0.64439(9) 0.2253(2) 0.0254(6) Uani d . . . 1.0 . .
F F1 0.9724(2) 0.53160(6) 0.23344(12) 0.0392(4) Uani d . . . 1.0 . .
F F2 1.1794(2) 0.58795(6) 0.22691(13) 0.0381(4) Uani d . . . 1.0 . .
F F4 0.5812(2) 0.62670(7) 0.05831(15) 0.0590(6) Uani d . . . 1.0 . .
F F5 0.8285(3) 0.67102(6) 0.05065(13) 0.0551(5) Uani d . . . 1.0 . .
F F7 1.0966(3) 0.54486(6) 0.01035(13) 0.0509(5) Uani d . . . 1.0 . .
F F8 0.8931(3) 0.59060(6) -0.09007(12) 0.0453(5) Uani d . . . 1.0 . .
N N1 1.0776(3) 0.58009(7) 0.45489(16) 0.0242(5) Uani d . . . 1.0 . .
N N2 0.5287(3) 0.70483(7) 0.21400(16) 0.0246(5) Uani d . . . 1.0 . .
C C23A 0.8764(8) 0.5864(2) 0.0951(4) 0.0224(12) Uani d . P . 0.776(14) . .
C C26A 1.0093(9) 0.58615(18) 0.0076(3) 0.0297(12) Uani d . P . 0.776(14) . .
F F3A 0.7434(6) 0.55118(17) 0.0657(4) 0.0318(9) Uani d . P . 0.776(14) . .
F F6A 1.1405(4) 0.62020(17) 0.0194(5) 0.0470(14) Uani d . P . 0.776(14) . .
C C23B 0.936(3) 0.6035(9) 0.0971(17) 0.035(5) Uani d . P . 0.224(14) . .
C C26B 0.908(4) 0.5704(7) 0.0107(12) 0.039(6) Uani d . P . 0.224(14) . .
F F3B 1.1034(16) 0.6326(3) 0.0784(16) 0.040(4) Uani d . P . 0.224(14) . .
F F6B 0.758(2) 0.5412(6) 0.023(2) 0.045(4) Uani d . P . 0.224(14) . .
S S1 0.84455(9) 0.58791(2) 0.59338(5) 0.02774(18) Uani d . . . 1.0 . .
S S2 0.66649(10) 0.76495(2) 0.36091(5) 0.03053(19) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.496(4) ?
C2 C3 . 1.373(3) ?
C2 S1 . 1.717(3) ?
C3 N1 . 1.386(3) ?
C3 C21 . 1.464(3) ?
C4 N1 . 1.308(3) ?
C4 C5 . 1.465(3) ?
C4 S1 . 1.738(2) ?
C5 C6 . 1.394(4) ?
C5 C10 . 1.395(4) ?
C6 C7 . 1.387(4) ?
C7 C8 . 1.379(4) ?
C8 C9 . 1.381(4) ?
C9 C10 . 1.380(4) ?
C11 C12 . 1.513(4) ?
C12 C13 . 1.362(4) ?
C12 S2 . 1.714(3) ?
C13 N2 . 1.385(3) ?
C13 C25 . 1.466(4) ?
C14 N2 . 1.301(3) ?
C14 C15 . 1.473(3) ?
C14 S2 . 1.737(2) ?
C15 C16 . 1.384(4) ?
C15 C20 . 1.388(4) ?
C16 C17 . 1.381(4) ?
C17 C18 . 1.387(4) ?
C18 C19 . 1.375(4) ?
C19 C20 . 1.384(4) ?
C21 C25 . 1.355(4) ?
C21 C22 . 1.498(4) ?
C22 F1 . 1.339(3) ?
C22 F2 . 1.368(3) ?
C22 C23A . 1.547(6) ?
C22 C23B . 1.599(18) ?
C24 F5 . 1.339(3) ?
C24 F4 . 1.344(3) ?
C24 C23B . 1.49(2) ?
C24 C25 . 1.497(4) ?
C24 C23A . 1.581(6) ?
F7 C26A . 1.313(4) ?
F7 C26B . 1.496(19) ?
F8 C26A . 1.344(4) ?
F8 C26B . 1.367(16) ?
C23A F3A . 1.362(9) ?
C23A C26A . 1.542(9) ?
C26A F6A . 1.315(8) ?
C23B C26B . 1.41(4) ?
C23B F3B . 1.47(3) ?
C26B F6B . 1.35(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C2 C1 . . 130.4(2) ?
C3 C2 S1 . . 108.55(18) ?
C1 C2 S1 . . 121.00(19) ?
C2 C3 N1 . . 116.4(2) ?
C2 C3 C21 . . 125.2(2) ?
N1 C3 C21 . . 118.3(2) ?
N1 C4 C5 . . 124.9(2) ?
N1 C4 S1 . . 113.99(18) ?
C5 C4 S1 . . 121.14(18) ?
C6 C5 C10 . . 119.2(2) ?
C6 C5 C4 . . 119.6(2) ?
C10 C5 C4 . . 121.3(2) ?
C7 C6 C5 . . 120.2(2) ?
C8 C7 C6 . . 119.9(3) ?
C7 C8 C9 . . 120.4(2) ?
C10 C9 C8 . . 120.2(3) ?
C9 C10 C5 . . 120.2(3) ?
C13 C12 C11 . . 130.1(3) ?
C13 C12 S2 . . 109.31(19) ?
C11 C12 S2 . . 120.6(2) ?
C12 C13 N2 . . 115.8(2) ?
C12 C13 C25 . . 125.4(2) ?
N2 C13 C25 . . 118.7(2) ?
N2 C14 C15 . . 124.5(2) ?
N2 C14 S2 . . 114.02(19) ?
C15 C14 S2 . . 121.47(19) ?
C16 C15 C20 . . 118.9(2) ?
C16 C15 C14 . . 119.9(2) ?
C20 C15 C14 . . 121.1(2) ?
C17 C16 C15 . . 120.5(3) ?
C16 C17 C18 . . 120.3(3) ?
C19 C18 C17 . . 119.5(3) ?
C18 C19 C20 . . 120.3(3) ?
C19 C20 C15 . . 120.5(3) ?
C25 C21 C3 . . 128.9(2) ?
C25 C21 C22 . . 110.5(2) ?
C3 C21 C22 . . 120.5(2) ?
F1 C22 F2 . . 105.45(19) ?
F1 C22 C21 . . 114.7(2) ?
F2 C22 C21 . . 110.1(2) ?
F1 C22 C23A . . 107.3(3) ?
F2 C22 C23A . . 113.1(3) ?
C21 C22 C23A . . 106.3(3) ?
F1 C22 C23B . . 127.2(10) ?
F2 C22 C23B . . 93.7(9) ?
C21 C22 C23B . . 103.1(9) ?
C23A C22 C23B . . 23.3(8) ?
F5 C24 F4 . . 105.6(2) ?
F5 C24 C23B . . 95.5(9) ?
F4 C24 C23B . . 125.1(11) ?
F5 C24 C25 . . 113.1(2) ?
F4 C24 C25 . . 112.3(2) ?
C23B C24 C25 . . 104.3(8) ?
F5 C24 C23A . . 115.0(3) ?
F4 C24 C23A . . 104.5(3) ?
C23B C24 C23A . . 23.7(9) ?
C25 C24 C23A . . 106.3(3) ?
C21 C25 C13 . . 128.5(2) ?
C21 C25 C24 . . 111.0(2) ?
C13 C25 C24 . . 120.4(2) ?
C26A F7 C26B . . 34.0(8) ?
C26A F8 C26B . . 36.0(10) ?
C4 N1 C3 . . 110.5(2) ?
C14 N2 C13 . . 110.8(2) ?
F3A C23A C26A . . 105.4(5) ?
F3A C23A C22 . . 109.6(4) ?
C26A C23A C22 . . 115.0(4) ?
F3A C23A C24 . . 110.2(4) ?
C26A C23A C24 . . 114.4(5) ?
C22 C23A C24 . . 102.2(3) ?
F7 C26A F6A . . 110.0(4) ?
F7 C26A F8 . . 108.0(3) ?
F6A C26A F8 . . 109.2(3) ?
F7 C26A C23A . . 108.3(5) ?
F6A C26A C23A . . 113.7(6) ?
F8 C26A C23A . . 107.6(5) ?
C26B C23B F3B . . 105.(2) ?
C26B C23B C24 . . 116.(2) ?
F3B C23B C24 . . 109.2(15) ?
C26B C23B C22 . . 111.6(19) ?
F3B C23B C22 . . 110.6(13) ?
C24 C23B C22 . . 104.2(12) ?
F6B C26B F8 . . 114.8(15) ?
F6B C26B C23B . . 109.(3) ?
F8 C26B C23B . . 113.7(19) ?
F6B C26B F7 . . 113.0(12) ?
F8 C26B F7 . . 97.2(12) ?
C23B C26B F7 . . 108.(2) ?
C2 S1 C4 . . 90.52(12) ?
C12 S2 C14 . . 90.01(12) ?

####################################################################### 
# 
# 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_ku0166
_audit_block_doi                 10.5517/ccdc.csd.cc28b52w
_database_code_depnum_ccdc_archive 'CCDC 2095137'
loop_
_audit_author_name
_audit_author_address
'yuma nakagawa'
;Ryukoku University
Japan
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H32 F6 N2 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         634.72

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   6.57040(10)
_cell_length_b                   16.6413(3)
_cell_length_c                   28.0569(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.4663(6)
_cell_angle_gamma                90
_cell_volume                     3058.43(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    191
_cell_measurement_theta_min      5.3177
_cell_measurement_theta_max      34.7288
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.036
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320

_exptl_absorpt_coefficient_mu    2.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           CuKa
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            23822
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33

_refine_special_details          
;
;

_reflns_number_total             5298
_reflns_number_gt                5213
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0854
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_number_reflns         5298
_refine_ls_number_parameters     396
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+1.5501P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0311 0.0180 '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'

_computing_data_collection       ?
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1351(2) 0.04668(9) 0.18314(5) 0.0252(3) Uani d . . . 1 . .
H H1A 0.0904 0.0857 0.1583 0.038 Uiso calc U . R 1 . .
H H1B 0.0347 0.0445 0.2072 0.038 Uiso calc U . R 1 . .
H H1C 0.1473 -0.0065 0.1687 0.038 Uiso calc U . R 1 . .
C C2 0.3379(2) 0.07169(8) 0.20644(5) 0.0194(3) Uani d . . . 1 . .
C C3 0.4672(2) 0.13043(8) 0.19351(5) 0.0166(3) Uani d . . . 1 . .
C C4 0.6594(2) 0.08719(8) 0.25638(5) 0.0179(3) Uani d . . . 1 . .
C C5 0.8242(2) 0.08376(8) 0.29474(5) 0.0187(3) Uani d . . . 1 . .
C C6 0.9794(2) 0.14097(8) 0.29773(5) 0.0219(3) Uani d . . . 1 . .
H H6 0.9835 0.1807 0.2735 0.026 Uiso calc U . R 1 . .
C C7 1.1283(2) 0.14060(8) 0.33572(6) 0.0244(3) Uani d . . . 1 . .
H H7 1.2328 0.1801 0.3369 0.029 Uiso calc U . R 1 . .
C C8 1.1278(2) 0.08327(8) 0.37225(5) 0.0227(3) Uani d . . . 1 . .
C C9 0.9730(2) 0.02564(9) 0.36828(5) 0.0242(3) Uani d . . . 1 . .
H H9 0.9689 -0.0144 0.3923 0.029 Uiso calc U . R 1 . .
C C10 0.8258(2) 0.02509(8) 0.33043(5) 0.0229(3) Uani d . . . 1 . .
H H10 0.7243 -0.0157 0.3286 0.027 Uiso calc U . R 1 . .
C C11 1.2871(3) 0.08105(9) 0.41510(6) 0.0294(4) Uani d . . . 1 . .
C C12 1.4534(4) 0.14472(12) 0.41134(9) 0.0544(6) Uani d . . . 1 . .
H H12A 1.5169 0.1379 0.3811 0.082 Uiso calc U . R 1 . .
H H12B 1.5573 0.1386 0.4381 0.082 Uiso calc U . R 1 . .
H H12C 1.3926 0.1984 0.4124 0.082 Uiso calc U . R 1 . .
C C13 1.3923(3) -0.00151(10) 0.41737(6) 0.0319(4) Uani d . . . 1 . .
H H13A 1.2914 -0.0433 0.4226 0.048 Uiso calc U . R 1 . .
H H13B 1.4992 -0.002 0.4438 0.048 Uiso calc U . R 1 . .
H H13C 1.4533 -0.0118 0.3872 0.048 Uiso calc U . R 1 . .
C C14 1.1807(4) 0.09332(13) 0.46142(6) 0.0497(5) Uani d . . . 1 . .
H H14A 1.1199 0.1471 0.4614 0.075 Uiso calc U . R 1 . .
H H14B 1.2809 0.0879 0.489 0.075 Uiso calc U . R 1 . .
H H14C 1.0734 0.0528 0.4634 0.075 Uiso calc U . R 1 . .
C C15 -0.1535(2) 0.32624(9) 0.17305(5) 0.0224(3) Uani d . . . 1 . .
H H15A -0.1782 0.3809 0.161 0.034 Uiso calc U . R 1 . .
H H15B -0.2647 0.3101 0.1923 0.034 Uiso calc U . R 1 . .
H H15C -0.1471 0.2892 0.146 0.034 Uiso calc U . R 1 . .
C C16 0.0447(2) 0.32381(8) 0.20326(5) 0.0159(3) Uani d . . . 1 . .
C C17 0.2297(2) 0.29054(8) 0.19560(4) 0.0142(3) Uani d . . . 1 . .
C C18 0.3131(2) 0.33395(8) 0.26911(5) 0.0149(3) Uani d . . . 1 . .
C C19 0.4375(2) 0.34757(8) 0.31417(5) 0.0152(3) Uani d . . . 1 . .
C C20 0.6175(2) 0.30389(8) 0.32334(5) 0.0184(3) Uani d . . . 1 . .
H H20 0.6603 0.2674 0.3001 0.022 Uiso calc U . R 1 . .
C C21 0.7340(2) 0.31346(8) 0.36619(5) 0.0193(3) Uani d . . . 1 . .
H H21 0.8567 0.2836 0.3717 0.023 Uiso calc U . R 1 . .
C C22 0.6755(2) 0.36617(8) 0.40167(5) 0.0162(3) Uani d . . . 1 . .
C C23 0.4978(2) 0.41063(8) 0.39150(5) 0.0181(3) Uani d . . . 1 . .
H H23 0.456 0.4478 0.4145 0.022 Uiso calc U . R 1 . .
C C24 0.3803(2) 0.40180(8) 0.34846(5) 0.0184(3) Uani d . . . 1 . .
H H24 0.2601 0.433 0.3424 0.022 Uiso calc U . R 1 . .
C C25 0.8041(2) 0.37156(8) 0.44955(5) 0.0191(3) Uani d . . . 1 . .
C C26 0.8168(3) 0.28793(9) 0.47262(5) 0.0263(3) Uani d . . . 1 . .
H H26A 0.6798 0.2703 0.4795 0.04 Uiso calc U . R 1 . .
H H26B 0.9047 0.2903 0.5025 0.04 Uiso calc U . R 1 . .
H H26C 0.874 0.2498 0.4507 0.04 Uiso calc U . R 1 . .
C C27 1.0203(3) 0.39984(12) 0.44074(6) 0.0369(4) Uani d . . . 1 . .
H H27A 1.081 0.3625 0.4189 0.055 Uiso calc U . R 1 . .
H H27B 1.1043 0.4014 0.4712 0.055 Uiso calc U . R 1 . .
H H27C 1.0137 0.4537 0.4266 0.055 Uiso calc U . R 1 . .
C C28 0.7118(3) 0.42882(9) 0.48460(5) 0.0262(3) Uani d . . . 1 . .
H H28A 0.7051 0.4831 0.471 0.039 Uiso calc U . R 1 . .
H H28B 0.7972 0.4293 0.5148 0.039 Uiso calc U . R 1 . .
H H28C 0.574 0.4107 0.4904 0.039 Uiso calc U . R 1 . .
C C29 0.4124(2) 0.18421(8) 0.15241(5) 0.0159(3) Uani d . . . 1 . .
C C30 0.4698(2) 0.16460(8) 0.10294(5) 0.0197(3) Uani d . . . 1 . .
C C31 0.4080(2) 0.23994(8) 0.07331(5) 0.0180(3) Uani d . . . 1 . .
C C32 0.2469(2) 0.28043(8) 0.10243(5) 0.0184(3) Uani d . . . 1 . .
C C33 0.2934(2) 0.24970(8) 0.15241(4) 0.0146(3) Uani d . . . 1 . .
F F1 0.36416(16) 0.09998(5) 0.08439(3) 0.0306(2) Uani d . . . 1 . .
F F2 0.67022(14) 0.14697(6) 0.10122(3) 0.0298(2) Uani d . . . 1 . .
F F3 0.33747(13) 0.22304(5) 0.02816(3) 0.02436(19) Uani d . . . 1 . .
F F4 0.57022(13) 0.28900(5) 0.07154(3) 0.02496(19) Uani d . . . 1 . .
F F5 0.05779(13) 0.25791(6) 0.08394(3) 0.0314(2) Uani d . . . 1 . .
F F6 0.25428(16) 0.36130(5) 0.09881(3) 0.0308(2) Uani d . . . 1 . .
N N1 0.64960(18) 0.13883(7) 0.22105(4) 0.0180(2) Uani d . . . 1 . .
N N2 0.37977(17) 0.29604(7) 0.23275(4) 0.0153(2) Uani d . . . 1 . .
S S1 0.05981(5) 0.36442(2) 0.25996(2) 0.01663(10) Uani d . . . 1 . .
S S2 0.44676(5) 0.02437(2) 0.25678(2) 0.02078(10) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.497(2) ?
C2 C3 . 1.363(2) ?
C2 S2 . 1.7231(14) ?
C3 N1 . 1.3816(18) ?
C3 C29 . 1.4818(19) ?
C4 N1 . 1.3097(18) ?
C4 C5 . 1.4674(19) ?
C4 S2 . 1.7454(14) ?
C5 C6 . 1.393(2) ?
C5 C10 . 1.398(2) ?
C6 C7 . 1.390(2) ?
C7 C8 . 1.400(2) ?
C8 C9 . 1.396(2) ?
C8 C11 . 1.532(2) ?
C9 C10 . 1.380(2) ?
C11 C12 . 1.532(3) ?
C11 C14 . 1.536(3) ?
C11 C13 . 1.537(2) ?
C15 C16 . 1.4979(19) ?
C16 C17 . 1.3680(19) ?
C16 S1 . 1.7242(13) ?
C17 N2 . 1.3810(17) ?
C17 C33 . 1.4780(18) ?
C18 N2 . 1.3039(17) ?
C18 C19 . 1.4685(18) ?
C18 S1 . 1.7397(13) ?
C19 C24 . 1.3919(19) ?
C19 C20 . 1.3951(19) ?
C20 C21 . 1.3830(19) ?
C21 C22 . 1.4027(19) ?
C22 C23 . 1.393(2) ?
C22 C25 . 1.5330(18) ?
C23 C24 . 1.3894(19) ?
C25 C28 . 1.528(2) ?
C25 C26 . 1.535(2) ?
C25 C27 . 1.535(2) ?
C29 C33 . 1.3413(19) ?
C29 C30 . 1.5022(18) ?
C30 F2 . 1.3537(17) ?
C30 F1 . 1.3611(17) ?
C30 C31 . 1.5413(19) ?
C31 F3 . 1.3441(15) ?
C31 F4 . 1.3463(16) ?
C31 C32 . 1.5421(19) ?
C32 F6 . 1.3508(16) ?
C32 F5 . 1.3611(16) ?
C32 C33 . 1.5014(18) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C2 C1 . . 129.45(13) ?
C3 C2 S2 . . 108.56(11) ?
C1 C2 S2 . . 121.98(11) ?
C2 C3 N1 . . 117.10(12) ?
C2 C3 C29 . . 121.45(13) ?
N1 C3 C29 . . 121.44(12) ?
N1 C4 C5 . . 124.78(13) ?
N1 C4 S2 . . 113.95(10) ?
C5 C4 S2 . . 121.15(10) ?
C6 C5 C10 . . 118.00(13) ?
C6 C5 C4 . . 120.84(12) ?
C10 C5 C4 . . 121.11(13) ?
C7 C6 C5 . . 120.76(13) ?
C6 C7 C8 . . 121.52(14) ?
C9 C8 C7 . . 116.93(14) ?
C9 C8 C11 . . 119.66(13) ?
C7 C8 C11 . . 123.40(14) ?
C10 C9 C8 . . 121.91(13) ?
C9 C10 C5 . . 120.84(14) ?
C8 C11 C12 . . 112.14(14) ?
C8 C11 C14 . . 109.43(14) ?
C12 C11 C14 . . 109.89(17) ?
C8 C11 C13 . . 109.38(12) ?
C12 C11 C13 . . 107.46(15) ?
C14 C11 C13 . . 108.45(14) ?
C17 C16 C15 . . 131.74(12) ?
C17 C16 S1 . . 108.41(10) ?
C15 C16 S1 . . 119.78(10) ?
C16 C17 N2 . . 116.45(11) ?
C16 C17 C33 . . 128.83(12) ?
N2 C17 C33 . . 114.72(11) ?
N2 C18 C19 . . 123.37(12) ?
N2 C18 S1 . . 113.66(10) ?
C19 C18 S1 . . 122.95(10) ?
C24 C19 C20 . . 118.75(12) ?
C24 C19 C18 . . 122.21(12) ?
C20 C19 C18 . . 119.03(12) ?
C21 C20 C19 . . 120.26(12) ?
C20 C21 C22 . . 121.69(13) ?
C23 C22 C21 . . 117.29(12) ?
C23 C22 C25 . . 122.99(12) ?
C21 C22 C25 . . 119.71(12) ?
C24 C23 C22 . . 121.46(12) ?
C23 C24 C19 . . 120.51(13) ?
C28 C25 C22 . . 112.40(12) ?
C28 C25 C26 . . 107.77(11) ?
C22 C25 C26 . . 108.95(11) ?
C28 C25 C27 . . 109.34(13) ?
C22 C25 C27 . . 109.32(11) ?
C26 C25 C27 . . 108.99(13) ?
C33 C29 C3 . . 126.66(12) ?
C33 C29 C30 . . 111.39(12) ?
C3 C29 C30 . . 121.64(12) ?
F2 C30 F1 . . 106.48(11) ?
F2 C30 C29 . . 113.25(11) ?
F1 C30 C29 . . 111.58(12) ?
F2 C30 C31 . . 111.90(12) ?
F1 C30 C31 . . 109.36(11) ?
C29 C30 C31 . . 104.31(11) ?
F3 C31 F4 . . 107.95(11) ?
F3 C31 C30 . . 113.27(11) ?
F4 C31 C30 . . 109.71(11) ?
F3 C31 C32 . . 112.95(11) ?
F4 C31 C32 . . 109.44(11) ?
C30 C31 C32 . . 103.44(11) ?
F6 C32 F5 . . 106.43(11) ?
F6 C32 C33 . . 113.81(11) ?
F5 C32 C33 . . 112.08(11) ?
F6 C32 C31 . . 111.41(11) ?
F5 C32 C31 . . 108.77(11) ?
C33 C32 C31 . . 104.34(11) ?
C29 C33 C17 . . 125.17(12) ?
C29 C33 C32 . . 110.68(11) ?
C17 C33 C32 . . 123.98(12) ?
C4 N1 C3 . . 110.24(12) ?
C18 N2 C17 . . 111.05(11) ?
C16 S1 C18 . . 90.43(6) ?
C2 S2 C4 . . 90.14(7) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
####################################################################### 
# 
# 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_uch101_thiamtbu
_audit_block_doi                 10.5517/ccdc.csd.cc28b53x
_database_code_depnum_ccdc_archive 'CCDC 2095138'
loop_
_audit_author_name
_audit_author_address
'yuma nakagawa'
;Ryukoku University
Japan
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H32 F6 N2 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         634.72

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   11.9900(5)
_cell_length_b                   21.3155(10)
_cell_length_c                   12.2134(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.3338(17)
_cell_angle_gamma                90
_cell_volume                     3116.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      2.5382
_cell_measurement_theta_max      24.9765
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320

_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            122967
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             5505
_reflns_number_gt                4684
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1576
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_number_reflns         5505
_refine_ls_number_parameters     396
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0846P)²+4.0631P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.078
_refine_diff_density_min         -0.544
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0171 0.0103 '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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5403(3) 0.38033(16) 1.0650(2) 0.0433(7) Uani d . . . 1 . .
H H1A 0.5106 0.3376 1.0691 0.065 Uiso calc U . R 1 . .
H H1B 0.5034 0.4073 1.1169 0.065 Uiso calc U . R 1 . .
H H1C 0.6209 0.3798 1.0836 0.065 Uiso calc U . R 1 . .
C C2 0.5188(2) 0.40521(12) 0.9511(2) 0.0312(6) Uani d . . . 1 . .
C C3 0.5889(2) 0.40989(11) 0.8677(2) 0.0260(5) Uani d . . . 1 . .
C C4 0.4411(2) 0.45294(12) 0.7810(2) 0.0276(5) Uani d . . . 1 . .
C C5 0.3686(2) 0.48141(11) 0.6930(2) 0.0274(5) Uani d . . . 1 . .
C C6 0.3965(2) 0.47516(12) 0.5843(2) 0.0322(6) Uani d . . . 1 . .
H H6 0.4621 0.4531 0.5672 0.039 Uiso calc U . R 1 . .
C C7 0.3277(2) 0.50132(14) 0.5017(2) 0.0363(6) Uani d . . . 1 . .
H H7 0.3466 0.4974 0.4275 0.044 Uiso calc U . R 1 . .
C C8 0.2313(2) 0.53328(13) 0.5260(2) 0.0339(6) Uani d . . . 1 . .
H H8 0.1848 0.5506 0.4681 0.041 Uiso calc U . R 1 . .
C C9 0.2018(2) 0.54028(12) 0.6333(2) 0.0303(6) Uani d . . . 1 . .
C C10 0.2723(2) 0.51390(12) 0.7162(2) 0.0300(6) Uani d . . . 1 . .
H H10 0.2539 0.5183 0.7904 0.036 Uiso calc U . R 1 . .
C C11 0.0996(2) 0.57846(14) 0.6630(2) 0.0375(7) Uani d . . . 1 . .
C C12 0.1434(3) 0.63907(17) 0.7183(4) 0.0654(10) Uani d . . . 1 . .
H H12A 0.0802 0.6654 0.7367 0.098 Uiso calc U . R 1 . .
H H12B 0.1896 0.6619 0.668 0.098 Uiso calc U . R 1 . .
H H12C 0.1884 0.6286 0.7854 0.098 Uiso calc U . R 1 . .
C C13 0.0264(3) 0.5979(2) 0.5622(3) 0.0777(13) Uani d . . . 1 . .
H H13A 0.0013 0.5604 0.5215 0.117 Uiso calc U . R 1 . .
H H13B 0.0696 0.6246 0.515 0.117 Uiso calc U . R 1 . .
H H13C -0.0387 0.6211 0.5855 0.117 Uiso calc U . R 1 . .
C C14 0.0310(3) 0.5422(2) 0.7395(4) 0.0757(13) Uani d . . . 1 . .
H H14A 0.0042 0.5035 0.7035 0.114 Uiso calc U . R 1 . .
H H14B -0.033 0.5676 0.759 0.114 Uiso calc U . R 1 . .
H H14C 0.0768 0.5317 0.806 0.114 Uiso calc U . R 1 . .
C C15 0.7695(3) 0.22807(16) 1.1090(2) 0.0448(8) Uani d . . . 1 . .
H H15A 0.8331 0.2013 1.093 0.067 Uiso calc U . R 1 . .
H H15B 0.7303 0.2099 1.1697 0.067 Uiso calc U . R 1 . .
H H15C 0.7965 0.2701 1.1296 0.067 Uiso calc U . R 1 . .
C C16 0.6907(2) 0.23249(12) 1.0090(2) 0.0301(6) Uani d . . . 1 . .
C C17 0.6790(2) 0.27651(11) 0.9277(2) 0.0246(5) Uani d . . . 1 . .
C C18 0.5367(2) 0.21569(12) 0.8719(2) 0.0267(5) Uani d . . . 1 . .
C C19 0.4382(2) 0.19316(12) 0.8062(2) 0.0277(5) Uani d . . . 1 . .
C C20 0.3805(2) 0.23480(12) 0.7355(2) 0.0277(5) Uani d . . . 1 . .
H H20 0.4072 0.2766 0.7295 0.033 Uiso calc U . R 1 . .
C C21 0.2852(2) 0.21685(13) 0.6737(2) 0.0314(6) Uani d . . . 1 . .
C C22 0.2495(3) 0.15449(15) 0.6844(2) 0.0428(7) Uani d . . . 1 . .
H H22 0.1849 0.1406 0.6426 0.051 Uiso calc U . R 1 . .
C C23 0.3058(3) 0.11319(15) 0.7539(3) 0.0477(8) Uani d . . . 1 . .
H H23 0.2795 0.0713 0.7596 0.057 Uiso calc U . R 1 . .
C C24 0.4007(3) 0.13188(13) 0.8157(2) 0.0389(7) Uani d . . . 1 . .
H H24 0.4394 0.1032 0.8639 0.047 Uiso calc U . R 1 . .
C C25 0.2178(2) 0.26200(14) 0.5988(2) 0.0361(6) Uani d . . . 1 . .
C C26 0.2081(3) 0.23582(19) 0.4817(3) 0.0581(9) Uani d . . . 1 . .
H H26A 0.1637 0.2646 0.4342 0.087 Uiso calc U . R 1 . .
H H26B 0.1715 0.1947 0.4818 0.087 Uiso calc U . R 1 . .
H H26C 0.2828 0.2314 0.4541 0.087 Uiso calc U . R 1 . .
C C27 0.2708(3) 0.32695(16) 0.5954(3) 0.0521(9) Uani d . . . 1 . .
H H27A 0.2752 0.3451 0.6692 0.078 Uiso calc U . R 1 . .
H H27B 0.2252 0.354 0.5458 0.078 Uiso calc U . R 1 . .
H H27C 0.3462 0.3234 0.5689 0.078 Uiso calc U . R 1 . .
C C28 0.1007(3) 0.26847(18) 0.6415(3) 0.0526(8) Uani d . . . 1 . .
H H28A 0.1065 0.285 0.7165 0.079 Uiso calc U . R 1 . .
H H28B 0.0644 0.2273 0.6412 0.079 Uiso calc U . R 1 . .
H H28C 0.0562 0.2973 0.5941 0.079 Uiso calc U . R 1 . .
C C29 0.7062(2) 0.38909(12) 0.8760(2) 0.0253(5) Uani d . . . 1 . .
C C30 0.7995(2) 0.43303(12) 0.8523(2) 0.0309(6) Uani d . . . 1 . .
C C31 0.9057(2) 0.39323(13) 0.8625(2) 0.0362(6) Uani d . . . 1 . .
C C32 0.8713(2) 0.33352(12) 0.9214(2) 0.0313(6) Uani d . . . 1 . .
C C33 0.7458(2) 0.33310(11) 0.91100(19) 0.0245(5) Uani d . . . 1 . .
F F1 0.80731(17) 0.48096(9) 0.9239(2) 0.0646(6) Uani d . . . 1 . .
F F2 0.78772(15) 0.45975(10) 0.75238(16) 0.0572(6) Uani d . . . 1 . .
F F3 0.99402(16) 0.42133(9) 0.9071(2) 0.0668(6) Uani d . . . 1 . .
F F4 0.93249(18) 0.37641(10) 0.75888(17) 0.0617(6) Uani d . . . 1 . .
F F5 0.91032(16) 0.33876(11) 1.02792(16) 0.0658(6) Uani d . . . 1 . .
F F6 0.91791(15) 0.28223(8) 0.8824(2) 0.0650(6) Uani d . . . 1 . .
N N1 0.54549(17) 0.43734(10) 0.77134(17) 0.0275(5) Uani d . . . 1 . .
N N2 0.59127(17) 0.26674(9) 0.85051(17) 0.0258(5) Uani d . . . 1 . .
S S1 0.39091(6) 0.43534(3) 0.90808(6) 0.0356(2) Uani d . . . 1 . .
S S2 0.58829(6) 0.17664(3) 0.98864(6) 0.0337(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.497(4) ?
C2 C3 . 1.362(4) ?
C2 S1 . 1.717(3) ?
C3 N1 . 1.389(3) ?
C3 C29 . 1.473(3) ?
C4 N1 . 1.307(3) ?
C4 C5 . 1.473(4) ?
C4 S1 . 1.738(3) ?
C5 C10 . 1.389(4) ?
C5 C6 . 1.394(4) ?
C6 C7 . 1.383(4) ?
C7 C8 . 1.388(4) ?
C8 C9 . 1.384(4) ?
C9 C10 . 1.399(4) ?
C9 C11 . 1.533(4) ?
C11 C14 . 1.495(5) ?
C11 C13 . 1.527(5) ?
C11 C12 . 1.536(5) ?
C15 C16 . 1.503(4) ?
C16 C17 . 1.367(4) ?
C16 S2 . 1.718(3) ?
C17 N2 . 1.387(3) ?
C17 C33 . 1.468(3) ?
C18 N2 . 1.304(3) ?
C18 C19 . 1.469(4) ?
C18 S2 . 1.733(3) ?
C19 C24 . 1.388(4) ?
C19 C20 . 1.394(4) ?
C20 C21 . 1.387(4) ?
C21 C22 . 1.405(4) ?
C21 C25 . 1.526(4) ?
C22 C23 . 1.373(5) ?
C23 C24 . 1.387(4) ?
C25 C27 . 1.525(4) ?
C25 C28 . 1.533(4) ?
C25 C26 . 1.534(4) ?
C29 C33 . 1.345(3) ?
C29 C30 . 1.500(4) ?
C30 F1 . 1.344(3) ?
C30 F2 . 1.347(3) ?
C30 C31 . 1.528(4) ?
C31 F3 . 1.308(3) ?
C31 F4 . 1.372(4) ?
C31 C32 . 1.530(4) ?
C32 F6 . 1.328(3) ?
C32 F5 . 1.362(3) ?
C32 C33 . 1.503(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C2 C1 . . 129.8(2) ?
C3 C2 S1 . . 108.84(19) ?
C1 C2 S1 . . 121.3(2) ?
C2 C3 N1 . . 116.6(2) ?
C2 C3 C29 . . 123.8(2) ?
N1 C3 C29 . . 119.6(2) ?
N1 C4 C5 . . 124.5(2) ?
N1 C4 S1 . . 114.12(19) ?
C5 C4 S1 . . 121.34(19) ?
C10 C5 C6 . . 119.4(2) ?
C10 C5 C4 . . 121.2(2) ?
C6 C5 C4 . . 119.4(2) ?
C7 C6 C5 . . 119.4(2) ?
C6 C7 C8 . . 120.7(3) ?
C9 C8 C7 . . 121.1(2) ?
C8 C9 C10 . . 117.7(2) ?
C8 C9 C11 . . 122.2(2) ?
C10 C9 C11 . . 120.0(2) ?
C5 C10 C9 . . 121.8(2) ?
C14 C11 C13 . . 109.4(3) ?
C14 C11 C9 . . 110.5(2) ?
C13 C11 C9 . . 112.5(3) ?
C14 C11 C12 . . 110.3(3) ?
C13 C11 C12 . . 107.0(3) ?
C9 C11 C12 . . 107.0(2) ?
C17 C16 C15 . . 131.8(3) ?
C17 C16 S2 . . 109.16(19) ?
C15 C16 S2 . . 119.0(2) ?
C16 C17 N2 . . 115.6(2) ?
C16 C17 C33 . . 129.1(2) ?
N2 C17 C33 . . 115.3(2) ?
N2 C18 C19 . . 124.0(2) ?
N2 C18 S2 . . 113.97(19) ?
C19 C18 S2 . . 121.97(19) ?
C24 C19 C20 . . 120.0(2) ?
C24 C19 C18 . . 121.0(2) ?
C20 C19 C18 . . 119.0(2) ?
C21 C20 C19 . . 121.7(2) ?
C20 C21 C22 . . 117.2(3) ?
C20 C21 C25 . . 122.9(2) ?
C22 C21 C25 . . 119.9(2) ?
C23 C22 C21 . . 121.5(3) ?
C22 C23 C24 . . 120.7(3) ?
C23 C24 C19 . . 118.9(3) ?
C27 C25 C21 . . 112.5(2) ?
C27 C25 C28 . . 108.6(3) ?
C21 C25 C28 . . 108.4(2) ?
C27 C25 C26 . . 108.3(3) ?
C21 C25 C26 . . 109.8(3) ?
C28 C25 C26 . . 109.2(3) ?
C33 C29 C3 . . 127.3(2) ?
C33 C29 C30 . . 111.3(2) ?
C3 C29 C30 . . 121.3(2) ?
F1 C30 F2 . . 105.5(2) ?
F1 C30 C29 . . 111.9(2) ?
F2 C30 C29 . . 113.5(2) ?
F1 C30 C31 . . 110.1(2) ?
F2 C30 C31 . . 110.6(2) ?
C29 C30 C31 . . 105.3(2) ?
F3 C31 F4 . . 106.1(2) ?
F3 C31 C30 . . 115.5(2) ?
F4 C31 C30 . . 108.0(2) ?
F3 C31 C32 . . 114.8(2) ?
F4 C31 C32 . . 107.5(2) ?
C30 C31 C32 . . 104.7(2) ?
F6 C32 F5 . . 106.3(2) ?
F6 C32 C33 . . 113.9(2) ?
F5 C32 C33 . . 111.6(2) ?
F6 C32 C31 . . 112.7(2) ?
F5 C32 C31 . . 107.1(2) ?
C33 C32 C31 . . 105.1(2) ?
C29 C33 C17 . . 126.0(2) ?
C29 C33 C32 . . 110.7(2) ?
C17 C33 C32 . . 123.0(2) ?
C4 N1 C3 . . 110.2(2) ?
C18 N2 C17 . . 111.0(2) ?
C2 S1 C4 . . 90.28(12) ?
C16 S2 C18 . . 90.24(12) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
