# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_uch202_a
_audit_block_doi                 10.5517/ccdc.csd.cc2hnjk8
_database_code_depnum_ccdc_archive 'CCDC 2313640'
loop_
_audit_author_name
_audit_author_address
'Ryotaro Shiromae'
;Ryukoku University
Japan
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H18 F6 N2 S2'
_chemical_formula_weight         572.57

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.59620(10)
_cell_length_b                   9.2091(2)
_cell_length_c                   42.8057(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.6450(10)
_cell_angle_gamma                90
_cell_volume                     2594.97(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    147017
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.57

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.496
_exptl_crystal_size_mid          0.383
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8770
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoKa
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            147014
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_theta_min         2.408
_diffrn_reflns_theta_max         27.568
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5978
_reflns_number_gt                5326
_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_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0659P)²+1.4693P] 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         5978
_refine_ls_number_parameters     392
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_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
C1 C 0.9614(4) 0.3012(2) 0.48700(5) 0.0522(5) Uani 1 1 d . . . . .
H1 H 0.8707 0.3781 0.4898 0.063 Uiso 1 1 calc R U . . .
C2 C 1.1333(4) 0.2866(3) 0.50704(5) 0.0601(6) Uani 1 1 d . . . . .
H2 H 1.1599 0.3540 0.5233 0.072 Uiso 1 1 calc R U . . .
C3 C 1.2659(4) 0.1724(3) 0.50310(6) 0.0643(6) Uani 1 1 d . . . . .
H3 H 1.3841 0.1632 0.5164 0.077 Uiso 1 1 calc R U . . .
C4 C 1.2245(4) 0.0732(3) 0.47988(7) 0.0775(9) Uani 1 1 d . . . . .
H4 H 1.3134 -0.0053 0.4776 0.093 Uiso 1 1 calc R U . . .
C5 C 1.0534(4) 0.0869(3) 0.45972(6) 0.0656(7) Uani 1 1 d . . . . .
H5 H 1.0261 0.0174 0.4439 0.079 Uiso 1 1 calc R U . . .
C6 C 0.9225(3) 0.2023(2) 0.46275(4) 0.0439(4) Uani 1 1 d . . . . .
C7 C 0.7438(3) 0.2225(2) 0.44085(4) 0.0424(4) Uani 1 1 d . . . . .
C8 C 0.4968(3) 0.33421(19) 0.41317(4) 0.0380(4) Uani 1 1 d . . . . .
C9 C 0.4562(3) 0.1975(2) 0.40196(5) 0.0478(5) Uani 1 1 d . . . . .
C10 C 0.2930(4) 0.1456(2) 0.37868(7) 0.0675(7) Uani 1 1 d . . . . .
H10A H 0.1873 0.2186 0.3762 0.101 Uiso 1 1 calc R U . . .
H10B H 0.2357 0.0559 0.3861 0.101 Uiso 1 1 calc R U . . .
H10C H 0.3505 0.1287 0.3587 0.101 Uiso 1 1 calc R U . . .
C11 C 0.3902(3) 0.46820(18) 0.40380(4) 0.0352(3) Uani 1 1 d . . . . .
C12 C 0.3442(4) 0.5766(2) 0.42836(5) 0.0528(5) Uani 1 1 d . . . . .
C13 C 0.1895(4) 0.6775(2) 0.41234(5) 0.0528(5) Uani 1 1 d . . . . .
C14 C 0.2196(3) 0.66030(19) 0.37759(4) 0.0412(4) Uani 1 1 d . . . . .
C15 C 0.3289(2) 0.51733(17) 0.37515(4) 0.0323(3) Uani 1 1 d . . . . .
C16 C 0.7495(3) 0.3827(3) 0.35413(5) 0.0569(6) Uani 1 1 d . . . . .
H16A H 0.7595 0.4519 0.3712 0.085 Uiso 1 1 calc R U . . .
H16B H 0.8595 0.3991 0.3405 0.085 Uiso 1 1 calc R U . . .
H16C H 0.7587 0.2848 0.3625 0.085 Uiso 1 1 calc R U . . .
C17 C 0.5504(3) 0.4017(2) 0.33586(4) 0.0399(4) Uani 1 1 d . . . . .
C18 C 0.3694(2) 0.45920(18) 0.34417(4) 0.0322(3) Uani 1 1 d . . . . .
C19 C 0.2759(3) 0.41387(19) 0.29455(4) 0.0349(3) Uani 1 1 d . . . . .
C20 C 0.1499(3) 0.40901(19) 0.26497(4) 0.0356(3) Uani 1 1 d . . . . .
C21 C 0.2106(3) 0.3248(2) 0.23942(5) 0.0452(4) Uani 1 1 d . . . . .
H21 H 0.3322 0.2714 0.2414 0.054 Uiso 1 1 calc R U . . .
C22 C 0.0940(3) 0.3206(2) 0.21197(5) 0.0504(5) Uani 1 1 d . . . . .
H22 H 0.1353 0.2633 0.1953 0.060 Uiso 1 1 calc R U . . .
C23 C -0.0878(3) 0.4010(2) 0.20822(4) 0.0441(4) Uani 1 1 d . . . . .
C24 C -0.2121(4) 0.3996(3) 0.17974(5) 0.0619(6) Uani 1 1 d . . . . .
H24 H -0.1740 0.3429 0.1628 0.074 Uiso 1 1 calc R U . . .
C25 C -0.3847(4) 0.4794(3) 0.17687(6) 0.0670(7) Uani 1 1 d . . . . .
H25 H -0.4646 0.4784 0.1579 0.080 Uiso 1 1 calc R U . . .
C26 C -0.4459(4) 0.5639(3) 0.20196(6) 0.0589(6) Uani 1 1 d . . . . .
H26 H -0.5665 0.6183 0.1997 0.071 Uiso 1 1 calc R U . . .
C27 C -0.3312(3) 0.5674(2) 0.22968(5) 0.0487(4) Uani 1 1 d . . . . .
H27 H -0.3733 0.6242 0.2463 0.058 Uiso 1 1 calc R U . . .
C28 C -0.1498(3) 0.48604(19) 0.23346(4) 0.0381(4) Uani 1 1 d . . . . .
C29 C -0.0267(3) 0.48709(19) 0.26179(4) 0.0374(4) Uani 1 1 d . . . . .
H29 H -0.0671 0.5425 0.2788 0.045 Uiso 1 1 calc R U . . .
F1A F 0.5156(3) 0.66099(19) 0.43558(5) 0.0716(8) Uani 0.868(5) 1 d . . P A 1
F2A F 0.2915(5) 0.5203(3) 0.45468(4) 0.0799(9) Uani 0.868(5) 1 d . . P A 1
F1B F 0.410(3) 0.5916(16) 0.4562(3) 0.080(6) Uani 0.132(5) 1 d . . P A 2
F2B F 0.114(3) 0.5020(13) 0.4409(4) 0.089(6) Uani 0.132(5) 1 d . . P A 2
F3A F 0.1935(5) 0.8123(2) 0.42211(5) 0.0732(8) Uani 0.863(5) 1 d . U P B 3
F4A F 0.0006(3) 0.6210(2) 0.41715(4) 0.0738(7) Uani 0.863(5) 1 d . U P B 3
F3B F 0.362(4) 0.8068(15) 0.4189(3) 0.097(6) Uani 0.137(5) 1 d . U P B 4
F4B F 0.054(3) 0.764(2) 0.4230(4) 0.097(6) Uani 0.137(5) 1 d . U P B 4
F5 F 0.3357(3) 0.77098(13) 0.36783(4) 0.0718(4) Uani 1 1 d . . . . .
F6 F 0.0437(2) 0.67100(16) 0.36044(3) 0.0721(4) Uani 1 1 d . . . . .
N1 N 0.6564(2) 0.34722(16) 0.43545(3) 0.0391(3) Uani 1 1 d . . . . .
N2 N 0.2164(2) 0.46698(16) 0.32066(3) 0.0338(3) Uani 1 1 d . . . . .
S1 S 0.63055(10) 0.07937(5) 0.41959(2) 0.05649(17) Uani 1 1 d . . . . .
S2 S 0.52464(7) 0.35236(6) 0.29699(2) 0.04785(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
C1 C2 1.384(3) . ?
C1 C6 1.392(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.385(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.364(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.471(3) . ?
C7 N1 1.299(2) . ?
C7 S1 1.743(2) . ?
C8 C9 1.368(3) . ?
C8 N1 1.380(2) . ?
C8 C11 1.464(2) . ?
C9 C10 1.497(3) . ?
C9 S1 1.722(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 C15 1.345(2) . ?
C11 C12 1.495(3) . ?
C12 F1B 1.252(11) . ?
C12 F2A 1.307(3) . ?
C12 F1A 1.391(3) . ?
C12 C13 1.512(3) . ?
C12 F2B 1.777(16) . ?
C13 F4B 1.306(13) . ?
C13 F3A 1.309(3) . ?
C13 F4A 1.378(3) . ?
C13 C14 1.521(3) . ?
C13 F3B 1.659(14) . ?
C14 F6 1.337(2) . ?
C14 F5 1.357(2) . ?
C14 C15 1.508(2) . ?
C15 C18 1.470(2) . ?
C16 C17 1.496(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 C18 1.373(2) . ?
C17 S2 1.7226(19) . ?
C18 N2 1.381(2) . ?
C19 N2 1.303(2) . ?
C19 C20 1.470(2) . ?
C19 S2 1.7327(17) . ?
C20 C29 1.369(2) . ?
C20 C21 1.419(2) . ?
C21 C22 1.363(3) . ?
C21 H21 0.9400 . ?
C22 C23 1.409(3) . ?
C22 H22 0.9400 . ?
C23 C28 1.416(3) . ?
C23 C24 1.426(3) . ?
C24 C25 1.354(4) . ?
C24 H24 0.9400 . ?
C25 C26 1.406(4) . ?
C25 H25 0.9400 . ?
C26 C27 1.366(3) . ?
C26 H26 0.9400 . ?
C27 C28 1.412(3) . ?
C27 H27 0.9400 . ?
C28 C29 1.416(3) . ?
C29 H29 0.9400 . ?

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
C2 C1 C6 120.25(19) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.11(19) . . ?
C5 C6 C7 121.23(18) . . ?
C1 C6 C7 119.66(17) . . ?
N1 C7 C6 123.64(17) . . ?
N1 C7 S1 113.92(14) . . ?
C6 C7 S1 122.44(14) . . ?
C9 C8 N1 116.48(16) . . ?
C9 C8 C11 126.88(16) . . ?
N1 C8 C11 116.64(15) . . ?
C8 C9 C10 130.02(18) . . ?
C8 C9 S1 108.50(14) . . ?
C10 C9 S1 121.47(15) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C11 C8 130.14(16) . . ?
C15 C11 C12 110.74(15) . . ?
C8 C11 C12 119.06(15) . . ?
F2A C12 F1A 106.7(2) . . ?
F1B C12 C11 132.2(6) . . ?
F2A C12 C11 114.7(2) . . ?
F1A C12 C11 109.34(19) . . ?
F1B C12 C13 123.2(6) . . ?
F2A C12 C13 115.2(2) . . ?
F1A C12 C13 105.82(19) . . ?
C11 C12 C13 104.64(16) . . ?
F1B C12 F2B 90.3(11) . . ?
C11 C12 F2B 99.7(5) . . ?
C13 C12 F2B 79.1(6) . . ?
F3A C13 F4A 108.1(2) . . ?
F4B C13 C12 132.6(7) . . ?
F3A C13 C12 116.0(2) . . ?
F4A C13 C12 106.9(2) . . ?
F4B C13 C14 122.8(7) . . ?
F3A C13 C14 114.2(2) . . ?
F4A C13 C14 106.41(19) . . ?
C12 C13 C14 104.66(16) . . ?
F4B C13 F3B 88.8(13) . . ?
C12 C13 F3B 85.9(7) . . ?
C14 C13 F3B 96.3(6) . . ?
F6 C14 F5 105.24(16) . . ?
F6 C14 C15 115.38(15) . . ?
F5 C14 C15 110.67(16) . . ?
F6 C14 C13 111.49(17) . . ?
F5 C14 C13 109.51(17) . . ?
C15 C14 C13 104.56(15) . . ?
C11 C15 C18 129.70(15) . . ?
C11 C15 C14 110.35(15) . . ?
C18 C15 C14 119.70(14) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C16 131.19(17) . . ?
C18 C17 S2 108.53(13) . . ?
C16 C17 S2 120.24(14) . . ?
C17 C18 N2 116.01(15) . . ?
C17 C18 C15 125.77(15) . . ?
N2 C18 C15 118.17(14) . . ?
N2 C19 C20 124.44(15) . . ?
N2 C19 S2 114.01(13) . . ?
C20 C19 S2 121.53(13) . . ?
C29 C20 C21 119.37(16) . . ?
C29 C20 C19 120.03(16) . . ?
C21 C20 C19 120.59(16) . . ?
C22 C21 C20 120.56(18) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.83(18) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C28 119.26(17) . . ?
C22 C23 C24 122.13(19) . . ?
C28 C23 C24 118.61(19) . . ?
C25 C24 C23 120.5(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.8(2) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C27 C26 C25 120.4(2) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 120.4(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C23 119.33(17) . . ?
C27 C28 C29 122.02(17) . . ?
C23 C28 C29 118.65(17) . . ?
C20 C29 C28 121.32(16) . . ?
C20 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C7 N1 C8 110.88(15) . . ?
C19 N2 C18 111.05(14) . . ?
C9 S1 C7 90.18(9) . . ?
C17 S2 C19 90.39(8) . . ?

_refine_diff_density_max         0.504
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_uch203_a
_audit_block_doi                 10.5517/ccdc.csd.cc2hnn61
_database_code_depnum_ccdc_archive 'CCDC 2313753'
loop_
_audit_author_name
_audit_author_address
'Ryotaro Shiromae'
;Ryukoku University
Japan
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H18 F6 N2 S2'
_chemical_formula_weight         572.57

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.59250(10)
_cell_length_b                   9.2167(2)
_cell_length_c                   42.8136(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.6330(10)
_cell_angle_gamma                90
_cell_volume                     2596.17(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    146012
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      27.56

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.496
_exptl_crystal_size_mid          0.383
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8770
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoKa
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            145973
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_theta_min         2.407
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5981
_reflns_number_gt                5275
_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_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0763P)²+1.9541P] 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         5981
_refine_ls_number_parameters     392
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1560
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.068
_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
C1 C 0.9622(4) 0.3016(3) 0.48678(6) 0.0550(6) Uani 1 1 d . . . . .
H1 H 0.8725 0.3778 0.4895 0.066 Uiso 1 1 calc R U . . .
C2 C 1.1341(5) 0.2869(3) 0.50681(7) 0.0639(7) Uani 1 1 d . . . . .
H2 H 1.1612 0.3535 0.5229 0.077 Uiso 1 1 calc R U . . .
C3 C 1.2661(5) 0.1715(4) 0.50276(7) 0.0664(8) Uani 1 1 d . . . . .
H3 H 1.3835 0.1620 0.5158 0.080 Uiso 1 1 calc R U . . .
C4 C 1.2233(5) 0.0730(4) 0.47973(8) 0.0815(11) Uani 1 1 d . . . . .
H4 H 1.3106 -0.0050 0.4774 0.098 Uiso 1 1 calc R U . . .
C5 C 1.0524(5) 0.0868(3) 0.45967(7) 0.0690(9) Uani 1 1 d . . . . .
H5 H 1.0243 0.0177 0.4442 0.083 Uiso 1 1 calc R U . . .
C6 C 0.9228(4) 0.2031(3) 0.46258(5) 0.0458(5) Uani 1 1 d . . . . .
C7 C 0.7444(4) 0.2232(3) 0.44078(5) 0.0443(5) Uani 1 1 d . . . . .
C8 C 0.4973(3) 0.3357(2) 0.41312(5) 0.0399(5) Uani 1 1 d . . . . .
C9 C 0.4560(4) 0.1985(3) 0.40189(6) 0.0504(6) Uani 1 1 d . . . . .
C10 C 0.2927(5) 0.1473(3) 0.37868(8) 0.0707(9) Uani 1 1 d . . . . .
H10A H 0.1881 0.2197 0.3763 0.106 Uiso 1 1 calc R U . . .
H10B H 0.2357 0.0586 0.3860 0.106 Uiso 1 1 calc R U . . .
H10C H 0.3493 0.1308 0.3589 0.106 Uiso 1 1 calc R U . . .
C11 C 0.3908(3) 0.4695(2) 0.40382(5) 0.0369(4) Uani 1 1 d . . . . .
C12 C 0.3459(5) 0.5779(3) 0.42832(6) 0.0547(6) Uani 1 1 d . . . . .
C13 C 0.1904(4) 0.6789(3) 0.41239(6) 0.0549(6) Uani 1 1 d . . . . .
C14 C 0.2200(4) 0.6614(2) 0.37758(5) 0.0431(5) Uani 1 1 d . . . . .
C15 C 0.3294(3) 0.5188(2) 0.37517(5) 0.0340(4) Uani 1 1 d . . . . .
C16 C 0.7499(3) 0.3831(4) 0.35408(7) 0.0590(7) Uani 1 1 d . . . . .
H16A H 0.7617 0.4533 0.3707 0.089 Uiso 1 1 calc R U . . .
H16B H 0.8587 0.3966 0.3405 0.089 Uiso 1 1 calc R U . . .
H16C H 0.7574 0.2871 0.3628 0.089 Uiso 1 1 calc R U . . .
C17 C 0.5506(3) 0.4023(3) 0.33585(5) 0.0416(5) Uani 1 1 d . . . . .
C18 C 0.3694(3) 0.4602(2) 0.34417(5) 0.0342(4) Uani 1 1 d . . . . .
C19 C 0.2757(3) 0.4148(2) 0.29462(5) 0.0363(4) Uani 1 1 d . . . . .
C20 C 0.1502(3) 0.4099(2) 0.26507(5) 0.0369(4) Uani 1 1 d . . . . .
C21 C 0.2109(4) 0.3258(3) 0.23950(6) 0.0469(5) Uani 1 1 d . . . . .
H21 H 0.3313 0.2731 0.2415 0.056 Uiso 1 1 calc R U . . .
C22 C 0.0942(4) 0.3216(3) 0.21210(6) 0.0527(6) Uani 1 1 d . . . . .
H22 H 0.1351 0.2650 0.1957 0.063 Uiso 1 1 calc R U . . .
C23 C -0.0872(4) 0.4017(3) 0.20831(5) 0.0458(5) Uani 1 1 d . . . . .
C24 C -0.2117(5) 0.4007(3) 0.17981(6) 0.0632(7) Uani 1 1 d . . . . .
H24 H -0.1741 0.3448 0.1630 0.076 Uiso 1 1 calc R U . . .
C25 C -0.3842(5) 0.4806(4) 0.17703(7) 0.0687(8) Uani 1 1 d . . . . .
H25 H -0.4634 0.4796 0.1583 0.082 Uiso 1 1 calc R U . . .
C26 C -0.4450(4) 0.5647(3) 0.20202(7) 0.0603(7) Uani 1 1 d . . . . .
H26 H -0.5643 0.6186 0.1997 0.072 Uiso 1 1 calc R U . . .
C27 C -0.3307(4) 0.5681(3) 0.22974(6) 0.0503(5) Uani 1 1 d . . . . .
H27 H -0.3726 0.6241 0.2462 0.060 Uiso 1 1 calc R U . . .
C28 C -0.1496(3) 0.4871(2) 0.23351(5) 0.0394(4) Uani 1 1 d . . . . .
C29 C -0.0265(3) 0.4880(2) 0.26187(5) 0.0384(4) Uani 1 1 d . . . . .
H29 H -0.0666 0.5428 0.2787 0.046 Uiso 1 1 calc R U . . .
F1A F 0.5167(3) 0.6623(2) 0.43547(5) 0.0747(9) Uani 0.872(6) 1 d . . P A 1
F2A F 0.2933(6) 0.5219(3) 0.45472(5) 0.0842(12) Uani 0.872(6) 1 d . . P A 1
F1B F 0.407(4) 0.5940(18) 0.4562(3) 0.077(6) Uani 0.128(6) 1 d . . P A 2
F2B F 0.115(4) 0.5041(16) 0.4410(5) 0.090(8) Uani 0.128(6) 1 d . . P A 2
F3A F 0.1948(6) 0.8135(2) 0.42212(5) 0.0765(9) Uani 0.872(5) 1 d . U P B 3
F4A F 0.0016(3) 0.6222(3) 0.41730(5) 0.0775(8) Uani 0.872(5) 1 d . U P B 3
F3B F 0.368(4) 0.8053(17) 0.4188(4) 0.088(6) Uani 0.128(5) 1 d . U P B 4
F4B F 0.052(3) 0.763(2) 0.4234(4) 0.088(5) Uani 0.128(5) 1 d . U P B 4
F5 F 0.3360(3) 0.77184(16) 0.36771(4) 0.0740(5) Uani 1 1 d . . . . .
F6 F 0.0434(3) 0.6719(2) 0.36055(4) 0.0745(5) Uani 1 1 d . . . . .
N1 N 0.6570(3) 0.3483(2) 0.43544(4) 0.0404(4) Uani 1 1 d . . . . .
N2 N 0.2166(2) 0.46837(19) 0.32068(4) 0.0351(4) Uani 1 1 d . . . . .
S1 S 0.63026(12) 0.08037(7) 0.41954(2) 0.0593(2) Uani 1 1 d . . . . .
S2 S 0.52475(9) 0.35315(8) 0.29699(2) 0.04994(18) 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 1.384(4) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.466(3) . ?
C7 N1 1.302(3) . ?
C7 S1 1.744(2) . ?
C8 C9 1.374(3) . ?
C8 N1 1.381(3) . ?
C8 C11 1.462(3) . ?
C9 C10 1.495(4) . ?
C9 S1 1.722(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C15 1.346(3) . ?
C11 C12 1.492(3) . ?
C12 F1B 1.246(14) . ?
C12 F2A 1.309(4) . ?
C12 F1A 1.387(4) . ?
C12 C13 1.514(4) . ?
C12 F2B 1.784(19) . ?
C13 F3A 1.309(3) . ?
C13 F4B 1.312(16) . ?
C13 F4A 1.378(4) . ?
C13 C14 1.524(3) . ?
C13 F3B 1.661(16) . ?
C14 F6 1.337(3) . ?
C14 F5 1.357(3) . ?
C14 C15 1.506(3) . ?
C15 C18 1.472(3) . ?
C16 C17 1.496(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.376(3) . ?
C17 S2 1.722(2) . ?
C18 N2 1.380(2) . ?
C19 N2 1.302(3) . ?
C19 C20 1.468(3) . ?
C19 S2 1.735(2) . ?
C20 C29 1.369(3) . ?
C20 C21 1.419(3) . ?
C21 C22 1.362(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.406(4) . ?
C22 H22 0.9300 . ?
C23 C28 1.417(3) . ?
C23 C24 1.426(3) . ?
C24 C25 1.354(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.400(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.365(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.409(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.417(3) . ?
C29 H29 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
C2 C1 C6 120.3(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 121.1(2) . . ?
C1 C6 C7 119.7(2) . . ?
N1 C7 C6 123.5(2) . . ?
N1 C7 S1 113.92(17) . . ?
C6 C7 S1 122.59(17) . . ?
C9 C8 N1 116.44(19) . . ?
C9 C8 C11 126.9(2) . . ?
N1 C8 C11 116.70(18) . . ?
C8 C9 C10 129.9(2) . . ?
C8 C9 S1 108.44(17) . . ?
C10 C9 S1 121.64(19) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C11 C8 130.1(2) . . ?
C15 C11 C12 110.66(19) . . ?
C8 C11 C12 119.12(19) . . ?
F2A C12 F1A 106.6(3) . . ?
F1B C12 C11 133.5(8) . . ?
F2A C12 C11 114.7(2) . . ?
F1A C12 C11 109.7(2) . . ?
F1B C12 C13 121.8(8) . . ?
F2A C12 C13 115.0(3) . . ?
F1A C12 C13 105.7(2) . . ?
C11 C12 C13 104.70(19) . . ?
F1B C12 F2B 89.0(13) . . ?
C11 C12 F2B 99.8(6) . . ?
C13 C12 F2B 78.8(8) . . ?
F3A C13 F4A 108.3(3) . . ?
F3A C13 C12 116.0(3) . . ?
F4B C13 C12 132.1(8) . . ?
F4A C13 C12 106.9(2) . . ?
F3A C13 C14 114.2(2) . . ?
F4B C13 C14 123.4(8) . . ?
F4A C13 C14 106.4(2) . . ?
C12 C13 C14 104.51(19) . . ?
F4B C13 F3B 91.3(14) . . ?
C12 C13 F3B 84.7(8) . . ?
C14 C13 F3B 96.0(7) . . ?
F6 C14 F5 105.3(2) . . ?
F6 C14 C15 115.47(18) . . ?
F5 C14 C15 110.58(19) . . ?
F6 C14 C13 111.4(2) . . ?
F5 C14 C13 109.6(2) . . ?
C15 C14 C13 104.52(18) . . ?
C11 C15 C18 129.55(19) . . ?
C11 C15 C14 110.50(18) . . ?
C18 C15 C14 119.73(18) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C16 131.2(2) . . ?
C18 C17 S2 108.54(16) . . ?
C16 C17 S2 120.19(17) . . ?
C17 C18 N2 115.98(18) . . ?
C17 C18 C15 125.74(18) . . ?
N2 C18 C15 118.23(17) . . ?
N2 C19 C20 124.57(18) . . ?
N2 C19 S2 114.06(15) . . ?
C20 C19 S2 121.33(15) . . ?
C29 C20 C21 119.4(2) . . ?
C29 C20 C19 119.96(19) . . ?
C21 C20 C19 120.7(2) . . ?
C22 C21 C20 120.5(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C28 119.3(2) . . ?
C22 C23 C24 122.3(2) . . ?
C28 C23 C24 118.4(2) . . ?
C25 C24 C23 120.4(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.9(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C27 C26 C25 120.5(3) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 120.3(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C29 122.0(2) . . ?
C27 C28 C23 119.4(2) . . ?
C29 C28 C23 118.6(2) . . ?
C20 C29 C28 121.31(19) . . ?
C20 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C7 N1 C8 110.87(18) . . ?
C19 N2 C18 111.09(17) . . ?
C9 S1 C7 90.29(11) . . ?
C17 S2 C19 90.32(10) . . ?

_refine_diff_density_max         0.510
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.071

