# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_2o
_database_code_depnum_ccdc_archive 'CCDC 2452875'
loop_
_audit_author_name
_audit_author_address
'Daichi Kitagawa'
;Osaka Metropolitan University
Japan
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2025-06-09 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         'C28 H22 F2 N2 S2'
_chemical_formula_sum            'C28 H22 F2 N2 S2'
_chemical_formula_weight         488.59

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.29400(10)
_cell_length_b                   22.7558(2)
_cell_length_c                   9.15490(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.8389(8)
_cell_angle_gamma                90
_cell_volume                     2349.96(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    10893
_cell_measurement_theta_min      3.8550
_cell_measurement_theta_max      76.5040

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.351
_shelx_estimated_absorpt_T_min   0.386
_shelx_estimated_absorpt_T_max   0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            15980
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.885
_diffrn_reflns_theta_max         77.237
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4792
_reflns_number_gt                4427
_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       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_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)+(0.0367P)²+0.9059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4792
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0777
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
F1 F -0.12684(7) 0.72693(3) 0.66104(8) 0.02210(17) Uani 1 1 d . . . . .
F2 F -0.16554(7) 0.68349(4) 0.38959(9) 0.02575(18) Uani 1 1 d . . . . .
N1 N 0.26437(9) 0.64142(5) 0.85102(11) 0.0160(2) Uani 1 1 d . . . . .
N2 N 0.12951(10) 0.51721(5) 0.34846(11) 0.0164(2) Uani 1 1 d . . . . .
C1 C 0.19239(12) 0.48724(6) 0.71629(14) 0.0186(3) Uani 1 1 d . . . . .
H1 H 0.1143 0.4944 0.6681 0.028 Uiso 1 1 calc R U . . .
H2 H 0.1856 0.4569 0.7915 0.028 Uiso 1 1 calc R U . . .
H3 H 0.2474 0.4739 0.6437 0.028 Uiso 1 1 calc R U . . .
C2 C 0.23799(11) 0.54293(6) 0.78595(13) 0.0159(2) Uani 1 1 d . . . . .
C3 C 0.20928(11) 0.60046(5) 0.75807(13) 0.0150(2) Uani 1 1 d . . . . .
C4 C 0.33556(11) 0.61640(6) 0.94873(13) 0.0164(2) Uani 1 1 d . . . . .
C5 C 0.40861(11) 0.64731(6) 1.06282(13) 0.0168(2) Uani 1 1 d . . . . .
C6 C 0.36848(12) 0.69902(6) 1.12927(14) 0.0202(3) Uani 1 1 d . . . . .
C7 C 0.44374(13) 0.72609(6) 1.23458(15) 0.0239(3) Uani 1 1 d . . . . .
H4 H 0.4181 0.7610 1.2802 0.029 Uiso 1 1 calc R U . . .
C8 C 0.55477(13) 0.70348(6) 1.27467(15) 0.0242(3) Uani 1 1 d . . . . .
H5 H 0.6045 0.7231 1.3458 0.029 Uiso 1 1 calc R U . . .
C9 C 0.59283(12) 0.65205(6) 1.21042(16) 0.0237(3) Uani 1 1 d . . . . .
H6 H 0.6683 0.6360 1.2381 0.028 Uiso 1 1 calc R U . . .
C10 C 0.51978(12) 0.62433(6) 1.10546(15) 0.0206(3) Uani 1 1 d . . . . .
H7 H 0.5458 0.5891 1.0617 0.025 Uiso 1 1 calc R U . . .
C11 C 0.24772(14) 0.72519(7) 1.09531(18) 0.0306(3) Uani 1 1 d . . . . .
H8 H 0.2311 0.7549 1.1690 0.046 Uiso 1 1 calc R U . . .
H9 H 0.1876 0.6941 1.0964 0.046 Uiso 1 1 calc R U . . .
H10 H 0.2459 0.7436 0.9984 0.046 Uiso 1 1 calc R U . . .
C12 C 0.11909(11) 0.62325(5) 0.64903(13) 0.0148(2) Uani 1 1 d . . . . .
C13 C 0.04257(11) 0.66662(5) 0.69943(13) 0.0163(2) Uani 1 1 d . . . . .
H11 H 0.0558 0.6824 0.7950 0.020 Uiso 1 1 calc R U . . .
C14 C -0.05111(11) 0.68644(5) 0.61190(14) 0.0168(2) Uani 1 1 d . . . . .
C15 C -0.07070(11) 0.66423(6) 0.47198(14) 0.0184(3) Uani 1 1 d . . . . .
C16 C 0.00533(12) 0.62360(6) 0.41766(14) 0.0179(3) Uani 1 1 d . . . . .
H12 H -0.0079 0.6094 0.3207 0.021 Uiso 1 1 calc R U . . .
C17 C 0.10267(11) 0.60290(5) 0.50438(13) 0.0157(2) Uani 1 1 d . . . . .
C18 C 0.38921(12) 0.60490(6) 0.50899(15) 0.0221(3) Uani 1 1 d . . . . .
H13 H 0.3485 0.6419 0.5284 0.033 Uiso 1 1 calc R U . . .
H14 H 0.4545 0.6124 0.4448 0.033 Uiso 1 1 calc R U . . .
H15 H 0.4208 0.5880 0.6014 0.033 Uiso 1 1 calc R U . . .
C19 C 0.30344(12) 0.56273(6) 0.43617(13) 0.0175(3) Uani 1 1 d . . . . .
C20 C 0.18243(11) 0.56119(5) 0.43329(13) 0.0157(2) Uani 1 1 d . . . . .
C21 C 0.20780(11) 0.48345(6) 0.29001(13) 0.0166(2) Uani 1 1 d . . . . .
C22 C 0.17319(11) 0.43658(6) 0.18445(13) 0.0165(2) Uani 1 1 d . . . . .
C23 C 0.06583(12) 0.44570(6) 0.10394(13) 0.0169(2) Uani 1 1 d . . . . .
H16 H 0.0208 0.4800 0.1213 0.020 Uiso 1 1 calc R U . . .
C24 C 0.02411(12) 0.40561(6) -0.00037(13) 0.0180(3) Uani 1 1 d . . . . .
H17 H -0.0487 0.4125 -0.0541 0.022 Uiso 1 1 calc R U . . .
C25 C 0.08981(12) 0.35525(6) -0.02560(14) 0.0195(3) Uani 1 1 d . . . . .
H18 H 0.0628 0.3277 -0.0979 0.023 Uiso 1 1 calc R U . . .
C26 C 0.19500(12) 0.34548(6) 0.05544(15) 0.0204(3) Uani 1 1 d . . . . .
H19 H 0.2387 0.3107 0.0383 0.025 Uiso 1 1 calc R U . . .
C27 C 0.23862(12) 0.38511(6) 0.16135(14) 0.0197(3) Uani 1 1 d . . . . .
C28 C 0.35131(13) 0.37029(7) 0.24898(18) 0.0295(3) Uani 1 1 d . . . . .
H20 H 0.3703 0.3287 0.2355 0.044 Uiso 1 1 calc R U . . .
H21 H 0.3405 0.3780 0.3528 0.044 Uiso 1 1 calc R U . . .
H22 H 0.4163 0.3946 0.2156 0.044 Uiso 1 1 calc R U . . .
S1 S 0.33913(3) 0.54001(2) 0.93366(3) 0.01765(9) Uani 1 1 d . . . . .
S2 S 0.35348(3) 0.50480(2) 0.33398(3) 0.01841(9) 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
F1 C14 1.3493(14) . ?
F2 C15 1.3522(15) . ?
N1 C4 1.3037(16) . ?
N1 C3 1.3884(16) . ?
N2 C21 1.3058(17) . ?
N2 C20 1.3841(16) . ?
C1 C2 1.4985(17) . ?
C2 C3 1.3697(18) . ?
C2 S1 1.7276(12) . ?
C3 C12 1.4840(17) . ?
C4 C5 1.4768(17) . ?
C4 S1 1.7445(13) . ?
C5 C10 1.3976(18) . ?
C5 C6 1.4098(18) . ?
C6 C7 1.3964(19) . ?
C6 C11 1.5064(19) . ?
C7 C8 1.388(2) . ?
C8 C9 1.388(2) . ?
C9 C10 1.3868(19) . ?
C12 C13 1.4048(18) . ?
C12 C17 1.4065(17) . ?
C13 C14 1.3715(18) . ?
C14 C15 1.3847(19) . ?
C15 C16 1.3717(19) . ?
C16 C17 1.4051(18) . ?
C17 C20 1.4812(18) . ?
C18 C19 1.4966(18) . ?
C19 C20 1.3661(18) . ?
C19 S2 1.7275(13) . ?
C21 C22 1.4789(17) . ?
C21 S2 1.7435(13) . ?
C22 C23 1.4029(18) . ?
C22 C27 1.4063(18) . ?
C23 C24 1.3862(18) . ?
C24 C25 1.3908(19) . ?
C25 C26 1.3870(19) . ?
C26 C27 1.3961(19) . ?
C27 C28 1.5086(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
C4 N1 C3 111.70(11) . . ?
C21 N2 C20 111.89(11) . . ?
C3 C2 C1 130.98(11) . . ?
C3 C2 S1 108.90(9) . . ?
C1 C2 S1 120.04(9) . . ?
C2 C3 N1 115.64(11) . . ?
C2 C3 C12 127.42(11) . . ?
N1 C3 C12 116.71(11) . . ?
N1 C4 C5 125.54(12) . . ?
N1 C4 S1 113.38(9) . . ?
C5 C4 S1 121.08(9) . . ?
C10 C5 C6 119.69(12) . . ?
C10 C5 C4 118.82(11) . . ?
C6 C5 C4 121.50(12) . . ?
C7 C6 C5 117.93(12) . . ?
C7 C6 C11 118.82(12) . . ?
C5 C6 C11 123.23(12) . . ?
C8 C7 C6 122.02(13) . . ?
C9 C8 C7 119.69(13) . . ?
C10 C9 C8 119.41(13) . . ?
C9 C10 C5 121.25(12) . . ?
C13 C12 C17 119.08(11) . . ?
C13 C12 C3 115.95(11) . . ?
C17 C12 C3 124.92(11) . . ?
C14 C13 C12 120.56(11) . . ?
F1 C14 C13 120.87(11) . . ?
F1 C14 C15 118.87(11) . . ?
C13 C14 C15 120.25(12) . . ?
F2 C15 C16 120.60(12) . . ?
F2 C15 C14 118.92(12) . . ?
C16 C15 C14 120.48(12) . . ?
C15 C16 C17 120.50(12) . . ?
C16 C17 C12 118.98(12) . . ?
C16 C17 C20 116.26(11) . . ?
C12 C17 C20 124.75(11) . . ?
C20 C19 C18 130.53(12) . . ?
C20 C19 S2 108.89(10) . . ?
C18 C19 S2 120.58(10) . . ?
C19 C20 N2 115.67(11) . . ?
C19 C20 C17 127.21(11) . . ?
N2 C20 C17 117.04(11) . . ?
N2 C21 C22 121.99(11) . . ?
N2 C21 S2 113.07(10) . . ?
C22 C21 S2 124.59(10) . . ?
C23 C22 C27 119.42(12) . . ?
C23 C22 C21 115.48(11) . . ?
C27 C22 C21 125.11(12) . . ?
C24 C23 C22 121.33(12) . . ?
C23 C24 C25 119.39(12) . . ?
C26 C25 C24 119.55(12) . . ?
C25 C26 C27 122.10(12) . . ?
C26 C27 C22 118.19(12) . . ?
C26 C27 C28 118.97(12) . . ?
C22 C27 C28 122.82(12) . . ?
C2 S1 C4 90.38(6) . . ?
C19 S2 C21 90.42(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 N1 176.09(12) . . . . ?
S1 C2 C3 N1 -0.54(14) . . . . ?
C1 C2 C3 C12 1.8(2) . . . . ?
S1 C2 C3 C12 -174.82(10) . . . . ?
C4 N1 C3 C2 0.59(16) . . . . ?
C4 N1 C3 C12 175.51(11) . . . . ?
C3 N1 C4 C5 179.31(12) . . . . ?
C3 N1 C4 S1 -0.35(13) . . . . ?
N1 C4 C5 C10 -145.82(13) . . . . ?
S1 C4 C5 C10 33.82(16) . . . . ?
N1 C4 C5 C6 34.38(19) . . . . ?
S1 C4 C5 C6 -145.99(11) . . . . ?
C10 C5 C6 C7 1.20(19) . . . . ?
C4 C5 C6 C7 -179.00(12) . . . . ?
C10 C5 C6 C11 -176.96(13) . . . . ?
C4 C5 C6 C11 2.8(2) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C11 C6 C7 C8 178.04(14) . . . . ?
C6 C7 C8 C9 -0.8(2) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C9 C10 C5 0.2(2) . . . . ?
C6 C5 C10 C9 -1.2(2) . . . . ?
C4 C5 C10 C9 178.98(12) . . . . ?
C2 C3 C12 C13 133.13(13) . . . . ?
N1 C3 C12 C13 -41.10(15) . . . . ?
C2 C3 C12 C17 -44.0(2) . . . . ?
N1 C3 C12 C17 141.73(12) . . . . ?
C17 C12 C13 C14 3.77(18) . . . . ?
C3 C12 C13 C14 -173.57(11) . . . . ?
C12 C13 C14 F1 178.18(11) . . . . ?
C12 C13 C14 C15 -0.58(19) . . . . ?
F1 C14 C15 F2 -0.49(18) . . . . ?
C13 C14 C15 F2 178.30(11) . . . . ?
F1 C14 C15 C16 179.12(11) . . . . ?
C13 C14 C15 C16 -2.09(19) . . . . ?
F2 C15 C16 C17 -178.91(11) . . . . ?
C14 C15 C16 C17 1.5(2) . . . . ?
C15 C16 C17 C12 1.73(19) . . . . ?
C15 C16 C17 C20 -177.30(12) . . . . ?
C13 C12 C17 C16 -4.30(18) . . . . ?
C3 C12 C17 C16 172.79(12) . . . . ?
C13 C12 C17 C20 174.63(11) . . . . ?
C3 C12 C17 C20 -8.3(2) . . . . ?
C18 C19 C20 N2 176.90(13) . . . . ?
S2 C19 C20 N2 -2.45(14) . . . . ?
C18 C19 C20 C17 0.2(2) . . . . ?
S2 C19 C20 C17 -179.11(10) . . . . ?
C21 N2 C20 C19 2.32(16) . . . . ?
C21 N2 C20 C17 179.34(11) . . . . ?
C16 C17 C20 C19 133.18(14) . . . . ?
C12 C17 C20 C19 -45.8(2) . . . . ?
C16 C17 C20 N2 -43.45(16) . . . . ?
C12 C17 C20 N2 137.59(12) . . . . ?
C20 N2 C21 C22 -174.52(11) . . . . ?
C20 N2 C21 S2 -1.04(13) . . . . ?
N2 C21 C22 C23 26.57(18) . . . . ?
S2 C21 C22 C23 -146.13(10) . . . . ?
N2 C21 C22 C27 -153.03(13) . . . . ?
S2 C21 C22 C27 34.27(18) . . . . ?
C27 C22 C23 C24 -1.44(19) . . . . ?
C21 C22 C23 C24 178.93(11) . . . . ?
C22 C23 C24 C25 0.14(19) . . . . ?
C23 C24 C25 C26 0.99(19) . . . . ?
C24 C25 C26 C27 -0.8(2) . . . . ?
C25 C26 C27 C22 -0.5(2) . . . . ?
C25 C26 C27 C28 177.71(13) . . . . ?
C23 C22 C27 C26 1.59(19) . . . . ?
C21 C22 C27 C26 -178.83(12) . . . . ?
C23 C22 C27 C28 -176.53(13) . . . . ?
C21 C22 C27 C28 3.1(2) . . . . ?
C3 C2 S1 C4 0.27(10) . . . . ?
C1 C2 S1 C4 -176.79(11) . . . . ?
N1 C4 S1 C2 0.05(10) . . . . ?
C5 C4 S1 C2 -179.63(11) . . . . ?
C20 C19 S2 C21 1.49(10) . . . . ?
C18 C19 S2 C21 -177.93(11) . . . . ?
N2 C21 S2 C19 -0.27(10) . . . . ?
C22 C21 S2 C19 173.00(11) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.045


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_4o
_database_code_depnum_ccdc_archive 'CCDC 2452877'
loop_
_audit_author_name
_audit_author_address
'Daichi Kitagawa'
;Osaka Metropolitan University
Japan
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2025-06-09 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         'C32 H30 F2 N2 S2'
_chemical_formula_sum            'C32 H30 F2 N2 S2'
_chemical_formula_weight         544.70

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'
N N 0.0311 0.0180 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.0612(3)
_cell_length_b                   12.19120(10)
_cell_length_c                   13.5755(2)
_cell_angle_alpha                90
_cell_angle_beta                 121.113(2)
_cell_angle_gamma                90
_cell_volume                     2700.86(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    7790
_cell_measurement_theta_min      4.5090
_cell_measurement_theta_max      78.4980

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    2.100
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92282
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            11688
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.527
_diffrn_reflns_theta_max         79.379
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2875
_reflns_number_gt                2709
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_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)+(0.0385P)²+2.9698P] 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         2875
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.31903(9) 0.57112(12) -0.04462(11) 0.0207(3) Uani 1 1 d . . . . .
H1 H 0.3565 0.6328 -0.0280 0.031 Uiso 1 1 calc R U . . .
H2 H 0.2633 0.5990 -0.0750 0.031 Uiso 1 1 calc R U . . .
H3 H 0.3199 0.5229 -0.1017 0.031 Uiso 1 1 calc R U . . .
C2 C 0.34550(7) 0.50786(11) 0.06389(11) 0.0149(3) Uani 1 1 d . . . . .
C3 C 0.40676(7) 0.52842(10) 0.17503(11) 0.0134(2) Uani 1 1 d . . . . .
C4 C 0.36349(7) 0.37167(10) 0.20876(10) 0.0131(2) Uani 1 1 d . . . . .
C5 C 0.35294(8) 0.27749(10) 0.26846(11) 0.0135(2) Uani 1 1 d . . . . .
C6 C 0.41937(8) 0.22381(10) 0.36192(11) 0.0139(2) Uani 1 1 d . . . . .
C7 C 0.40193(8) 0.13824(11) 0.41465(12) 0.0187(3) Uani 1 1 d . . . . .
H4 H 0.4461 0.1019 0.4786 0.022 Uiso 1 1 calc R U . . .
C8 C 0.32240(9) 0.10461(11) 0.37678(12) 0.0207(3) Uani 1 1 d . . . . .
H5 H 0.3126 0.0466 0.4149 0.025 Uiso 1 1 calc R U . . .
C9 C 0.25712(8) 0.15620(11) 0.28277(12) 0.0192(3) Uani 1 1 d . . . . .
H6 H 0.2025 0.1328 0.2552 0.023 Uiso 1 1 calc R U . . .
C10 C 0.27252(8) 0.24220(11) 0.22968(11) 0.0160(3) Uani 1 1 d . . . . .
H7 H 0.2279 0.2780 0.1659 0.019 Uiso 1 1 calc R U . . .
C11 C 0.50825(7) 0.25521(10) 0.40821(11) 0.0145(2) Uani 1 1 d . . . . .
H8 H 0.5104 0.3007 0.3485 0.017 Uiso 1 1 calc R U . . .
C12 C 0.54003(8) 0.32539(12) 0.51672(12) 0.0211(3) Uani 1 1 d . . . . .
H9 H 0.5067 0.3920 0.4981 0.032 Uiso 1 1 calc R U . . .
H10 H 0.5972 0.3456 0.5459 0.032 Uiso 1 1 calc R U . . .
H11 H 0.5364 0.2835 0.5756 0.032 Uiso 1 1 calc R U . . .
C13 C 0.56268(9) 0.15451(12) 0.43198(14) 0.0256(3) Uani 1 1 d . . . . .
H12 H 0.5690 0.1151 0.4990 0.038 Uiso 1 1 calc R U . . .
H13 H 0.6166 0.1779 0.4473 0.038 Uiso 1 1 calc R U . . .
H14 H 0.5373 0.1060 0.3648 0.038 Uiso 1 1 calc R U . . .
C14 C 0.45695(8) 0.62988(10) 0.21352(10) 0.0139(2) Uani 1 1 d . . . . .
C15 C 0.41563(8) 0.73022(11) 0.17865(11) 0.0164(3) Uani 1 1 d . . . . .
H15 H 0.3577 0.7311 0.1296 0.020 Uiso 1 1 calc R U . . .
C16 C 0.45792(9) 0.82782(11) 0.21452(12) 0.0188(3) Uani 1 1 d . . . . .
S1 S 0.29831(2) 0.38610(2) 0.06036(2) 0.01409(10) Uani 1 1 d . . . . .
F1 F 0.41698(5) 0.92400(7) 0.18163(8) 0.0270(2) Uani 1 1 d . . . . .
N1 N 0.41664(6) 0.45111(9) 0.25608(9) 0.0133(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
C1 C2 1.5004(17) . ?
C2 C3 1.3718(18) . ?
C2 S1 1.7234(13) . ?
C3 N1 1.3857(16) . ?
C3 C14 1.4838(17) . ?
C4 N1 1.3055(16) . ?
C4 C5 1.4779(17) . ?
C4 S1 1.7454(12) . ?
C5 C10 1.4065(18) . ?
C5 C6 1.4075(18) . ?
C6 C7 1.3989(18) . ?
C6 C11 1.5205(17) . ?
C7 C8 1.3874(19) . ?
C8 C9 1.390(2) . ?
C9 C10 1.3869(19) . ?
C11 C13 1.5303(18) . ?
C11 C12 1.5319(18) . ?
C14 C15 1.3984(18) . ?
C15 C16 1.3772(19) . ?
C16 F1 1.3503(15) . ?

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
C3 C2 C1 130.48(12) . . ?
C3 C2 S1 108.87(9) . . ?
C1 C2 S1 120.63(10) . . ?
C2 C3 N1 115.99(11) . . ?
C2 C3 C14 124.55(11) . . ?
N1 C3 C14 119.28(11) . . ?
N1 C4 C5 126.68(11) . . ?
N1 C4 S1 113.69(9) . . ?
C5 C4 S1 119.60(9) . . ?
C10 C5 C6 119.60(12) . . ?
C10 C5 C4 117.60(11) . . ?
C6 C5 C4 122.79(11) . . ?
C7 C6 C5 117.84(12) . . ?
C7 C6 C11 119.01(11) . . ?
C5 C6 C11 123.14(11) . . ?
C8 C7 C6 122.26(12) . . ?
C7 C8 C9 119.67(12) . . ?
C10 C9 C8 119.33(12) . . ?
C9 C10 C5 121.28(12) . . ?
C6 C11 C13 111.99(11) . . ?
C6 C11 C12 109.91(10) . . ?
C13 C11 C12 110.93(11) . . ?
C15 C14 C3 117.53(11) . . ?
C16 C15 C14 120.78(12) . . ?
F1 C16 C15 120.05(12) . . ?
C2 S1 C4 90.27(6) . . ?
C4 N1 C3 111.19(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 N1 -178.43(13) . . . . ?
S1 C2 C3 N1 -0.23(14) . . . . ?
C1 C2 C3 C14 6.6(2) . . . . ?
S1 C2 C3 C14 -175.22(10) . . . . ?
N1 C4 C5 C10 141.08(13) . . . . ?
S1 C4 C5 C10 -36.67(15) . . . . ?
N1 C4 C5 C6 -38.16(19) . . . . ?
S1 C4 C5 C6 144.09(11) . . . . ?
C10 C5 C6 C7 -1.63(18) . . . . ?
C4 C5 C6 C7 177.59(12) . . . . ?
C10 C5 C6 C11 178.96(11) . . . . ?
C4 C5 C6 C11 -1.82(19) . . . . ?
C5 C6 C7 C8 0.9(2) . . . . ?
C11 C6 C7 C8 -179.61(12) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C10 -1.3(2) . . . . ?
C8 C9 C10 C5 0.6(2) . . . . ?
C6 C5 C10 C9 0.89(19) . . . . ?
C4 C5 C10 C9 -178.38(12) . . . . ?
C7 C6 C11 C13 45.02(16) . . . . ?
C5 C6 C11 C13 -135.58(13) . . . . ?
C7 C6 C11 C12 -78.76(15) . . . . ?
C5 C6 C11 C12 100.65(14) . . . . ?
C2 C3 C14 C15 48.40(18) . . . . ?
N1 C3 C14 C15 -126.43(13) . . . . ?
C3 C14 C15 C16 177.59(12) . . . . ?
C14 C15 C16 F1 -178.91(12) . . . . ?
C3 C2 S1 C4 0.52(10) . . . . ?
C1 C2 S1 C4 178.93(11) . . . . ?
N1 C4 S1 C2 -0.74(10) . . . . ?
C5 C4 S1 C2 177.28(10) . . . . ?
C5 C4 N1 C3 -177.13(11) . . . . ?
S1 C4 N1 C3 0.73(13) . . . . ?
C2 C3 N1 C4 -0.32(16) . . . . ?
C14 C3 N1 C4 174.95(11) . . . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.049


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_5o
_database_code_depnum_ccdc_archive 'CCDC 2452878'
loop_
_audit_author_name
_audit_author_address
'Daichi Kitagawa'
;Osaka Metropolitan University
Japan
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2025-06-09 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         'C34 H34 F2 N2 S2'
_chemical_formula_sum            'C34 H34 F2 N2 S2'
_chemical_formula_weight         572.75

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'
N N 0.0311 0.0180 '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'

_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                   14.52300(10)
_cell_length_b                   10.63980(10)
_cell_length_c                   19.0421(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.6399(8)
_cell_angle_gamma                90
_cell_volume                     2941.21(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    16399
_cell_measurement_theta_min      3.7530
_cell_measurement_theta_max      78.5430

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.953
_shelx_estimated_absorpt_T_min   0.662
_shelx_estimated_absorpt_T_max   0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            25746
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.776
_diffrn_reflns_theta_max         79.805
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6240
_reflns_number_gt                5776
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_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)+(0.0361P)²+2.2224P] 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         6240
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
F1 F -0.07146(6) 0.34220(10) 0.03369(5) 0.0293(2) Uani 1 1 d . . . . .
F2 F -0.05652(7) 0.12108(10) -0.03475(6) 0.0310(2) Uani 1 1 d . . . . .
C1 C 0.34092(12) 0.42234(16) -0.08713(8) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.3844 0.3527 -0.0918 0.037 Uiso 1 1 calc R U . . .
H2 H 0.3658 0.4977 -0.1093 0.037 Uiso 1 1 calc R U . . .
H3 H 0.2819 0.4000 -0.1101 0.037 Uiso 1 1 calc R U . . .
C2 C 0.32658(11) 0.44771(15) -0.01092(8) 0.0211(3) Uani 1 1 d . . . . .
C3 C 0.25724(11) 0.41088(14) 0.03192(8) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.33776(11) 0.52132(15) 0.11118(8) 0.0206(3) Uani 1 1 d . . . . .
C5 C 0.37090(10) 0.57003(15) 0.18059(8) 0.0204(3) Uani 1 1 d . . . . .
C6 C 0.33571(10) 0.67804(15) 0.21310(8) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.36634(12) 0.69950(16) 0.28289(9) 0.0257(3) Uani 1 1 d . . . . .
H25 H 0.3421 0.7692 0.3075 0.031 Uiso 1 1 calc R U . . .
C8 C 0.43042(13) 0.62306(17) 0.31713(9) 0.0288(4) Uani 1 1 d . . . . .
H26 H 0.4485 0.6405 0.3645 0.035 Uiso 1 1 calc R U . . .
C9 C 0.46832(12) 0.52134(17) 0.28283(9) 0.0280(4) Uani 1 1 d . . . . .
H27 H 0.5141 0.4705 0.3054 0.034 Uiso 1 1 calc R U . . .
C10 C 0.43778(11) 0.49571(16) 0.21474(9) 0.0244(3) Uani 1 1 d . . . . .
H28 H 0.4629 0.4260 0.1907 0.029 Uiso 1 1 calc R U . . .
C11 C 0.26470(11) 0.76791(15) 0.17884(9) 0.0235(3) Uani 1 1 d . . . . .
C12 C 0.27487(13) 0.78445(17) 0.09937(9) 0.0303(4) Uani 1 1 d . . . . .
H4 H 0.3393 0.8029 0.0894 0.045 Uiso 1 1 calc R U . . .
H5 H 0.2358 0.8541 0.0828 0.045 Uiso 1 1 calc R U . . .
H6 H 0.2560 0.7069 0.0752 0.045 Uiso 1 1 calc R U . . .
C13 C 0.16771(12) 0.71678(18) 0.19288(11) 0.0323(4) Uani 1 1 d . . . . .
H7 H 0.1214 0.7730 0.1716 0.048 Uiso 1 1 calc R U . . .
H8 H 0.1590 0.7121 0.2437 0.048 Uiso 1 1 calc R U . . .
H9 H 0.1611 0.6327 0.1723 0.048 Uiso 1 1 calc R U . . .
C14 C 0.27489(13) 0.90050(16) 0.21063(10) 0.0291(4) Uani 1 1 d . . . . .
H10 H 0.3379 0.9307 0.2046 0.044 Uiso 1 1 calc R U . . .
H11 H 0.2618 0.8974 0.2608 0.044 Uiso 1 1 calc R U . . .
H12 H 0.2314 0.9577 0.1867 0.044 Uiso 1 1 calc R U . . .
C15 C 0.17734(11) 0.32939(14) 0.01321(8) 0.0188(3) Uani 1 1 d . . . . .
C16 C 0.08988(11) 0.37169(15) 0.03222(8) 0.0210(3) Uani 1 1 d . . . . .
H29 H 0.0840 0.4491 0.0566 0.025 Uiso 1 1 calc R U . . .
C17 C 0.01272(11) 0.30155(15) 0.01572(8) 0.0222(3) Uani 1 1 d . . . . .
C18 C 0.02033(11) 0.18851(15) -0.01964(8) 0.0231(3) Uani 1 1 d . . . . .
C19 C 0.10504(11) 0.14433(15) -0.03815(8) 0.0228(3) Uani 1 1 d . . . . .
H30 H 0.1095 0.0668 -0.0626 0.027 Uiso 1 1 calc R U . . .
C20 C 0.18507(11) 0.21310(14) -0.02122(8) 0.0194(3) Uani 1 1 d . . . . .
C21 C 0.37296(13) 0.17242(17) 0.07291(9) 0.0292(4) Uani 1 1 d . . . . .
H13 H 0.4121 0.2473 0.0770 0.044 Uiso 1 1 calc R U . . .
H14 H 0.4048 0.1007 0.0950 0.044 Uiso 1 1 calc R U . . .
H15 H 0.3149 0.1876 0.0965 0.044 Uiso 1 1 calc R U . . .
C22 C 0.35325(11) 0.14424(15) -0.00332(8) 0.0233(3) Uani 1 1 d . . . . .
C23 C 0.27372(11) 0.15776(14) -0.04281(8) 0.0195(3) Uani 1 1 d . . . . .
C24 C 0.35735(11) 0.06900(14) -0.12530(8) 0.0206(3) Uani 1 1 d . . . . .
C25 C 0.38488(10) 0.01256(14) -0.19284(8) 0.0196(3) Uani 1 1 d . . . . .
C26 C 0.35131(10) -0.10438(14) -0.21854(8) 0.0197(3) Uani 1 1 d . . . . .
C27 C 0.38011(11) -0.13962(15) -0.28534(8) 0.0236(3) Uani 1 1 d . . . . .
H31 H 0.3582 -0.2167 -0.3047 0.028 Uiso 1 1 calc R U . . .
C28 C 0.43918(12) -0.06689(16) -0.32443(9) 0.0268(3) Uani 1 1 d . . . . .
H32 H 0.4558 -0.0937 -0.3699 0.032 Uiso 1 1 calc R U . . .
C29 C 0.47399(12) 0.04462(17) -0.29732(9) 0.0271(3) Uani 1 1 d . . . . .
H33 H 0.5158 0.0938 -0.3232 0.032 Uiso 1 1 calc R U . . .
C30 C 0.44664(11) 0.08317(15) -0.23148(9) 0.0239(3) Uani 1 1 d . . . . .
H34 H 0.4705 0.1593 -0.2123 0.029 Uiso 1 1 calc R U . . .
C31 C 0.28521(11) -0.19062(15) -0.17888(8) 0.0218(3) Uani 1 1 d . . . . .
C32 C 0.31121(13) -0.20284(16) -0.10018(9) 0.0279(4) Uani 1 1 d . . . . .
H16 H 0.3766 -0.2248 -0.0947 0.042 Uiso 1 1 calc R U . . .
H17 H 0.2737 -0.2688 -0.0792 0.042 Uiso 1 1 calc R U . . .
H18 H 0.2999 -0.1227 -0.0766 0.042 Uiso 1 1 calc R U . . .
C33 C 0.18643(12) -0.13974(17) -0.18774(9) 0.0277(3) Uani 1 1 d . . . . .
H19 H 0.1835 -0.0547 -0.1682 0.042 Uiso 1 1 calc R U . . .
H20 H 0.1441 -0.1947 -0.1629 0.042 Uiso 1 1 calc R U . . .
H21 H 0.1687 -0.1374 -0.2378 0.042 Uiso 1 1 calc R U . . .
C34 C 0.28607(12) -0.32465(15) -0.20946(9) 0.0264(3) Uani 1 1 d . . . . .
H22 H 0.2635 -0.3226 -0.2584 0.040 Uiso 1 1 calc R U . . .
H23 H 0.2462 -0.3790 -0.1820 0.040 Uiso 1 1 calc R U . . .
H24 H 0.3491 -0.3576 -0.2074 0.040 Uiso 1 1 calc R U . . .
S1 S 0.40432(3) 0.53718(4) 0.03793(2) 0.02310(10) Uani 1 1 d . . . . .
S2 S 0.43673(3) 0.08148(4) -0.05613(2) 0.02461(10) Uani 1 1 d . . . . .
N1 N 0.26381(9) 0.45348(12) 0.10089(7) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.27605(9) 0.11294(12) -0.11125(7) 0.0198(3) 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
F1 C17 1.3501(18) . ?
F2 C18 1.3508(18) . ?
C1 C2 1.497(2) . ?
C2 C3 1.371(2) . ?
C2 S1 1.7280(16) . ?
C3 N1 1.3901(19) . ?
C3 C15 1.484(2) . ?
C4 N1 1.304(2) . ?
C4 C5 1.487(2) . ?
C4 S1 1.7280(16) . ?
C5 C10 1.398(2) . ?
C5 C6 1.408(2) . ?
C6 C7 1.408(2) . ?
C6 C11 1.538(2) . ?
C7 C8 1.385(3) . ?
C8 C9 1.386(3) . ?
C9 C10 1.385(2) . ?
C11 C12 1.535(2) . ?
C11 C13 1.540(2) . ?
C11 C14 1.541(2) . ?
C15 C16 1.405(2) . ?
C15 C20 1.406(2) . ?
C16 C17 1.375(2) . ?
C17 C18 1.384(2) . ?
C18 C19 1.372(2) . ?
C19 C20 1.403(2) . ?
C20 C23 1.484(2) . ?
C21 C22 1.502(2) . ?
C22 C23 1.368(2) . ?
C22 S2 1.7311(16) . ?
C23 N2 1.3891(19) . ?
C24 N2 1.305(2) . ?
C24 C25 1.485(2) . ?
C24 S2 1.7306(16) . ?
C25 C30 1.396(2) . ?
C25 C26 1.418(2) . ?
C26 C27 1.401(2) . ?
C26 C31 1.541(2) . ?
C27 C28 1.388(2) . ?
C28 C29 1.384(2) . ?
C29 C30 1.388(2) . ?
C31 C33 1.538(2) . ?
C31 C32 1.540(2) . ?
C31 C34 1.541(2) . ?

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
C3 C2 C1 130.56(15) . . ?
C3 C2 S1 108.48(12) . . ?
C1 C2 S1 120.96(12) . . ?
C2 C3 N1 115.92(14) . . ?
C2 C3 C15 127.36(14) . . ?
N1 C3 C15 116.71(13) . . ?
N1 C4 C5 124.80(14) . . ?
N1 C4 S1 114.21(12) . . ?
C5 C4 S1 120.61(11) . . ?
C10 C5 C6 120.87(15) . . ?
C10 C5 C4 114.78(14) . . ?
C6 C5 C4 124.26(14) . . ?
C7 C6 C5 116.01(15) . . ?
C7 C6 C11 119.30(14) . . ?
C5 C6 C11 124.63(14) . . ?
C8 C7 C6 122.61(16) . . ?
C7 C8 C9 120.49(16) . . ?
C10 C9 C8 118.28(16) . . ?
C9 C10 C5 121.56(16) . . ?
C12 C11 C6 114.03(13) . . ?
C12 C11 C13 109.02(14) . . ?
C6 C11 C13 108.20(13) . . ?
C12 C11 C14 105.75(14) . . ?
C6 C11 C14 110.31(13) . . ?
C13 C11 C14 109.47(14) . . ?
C16 C15 C20 119.13(14) . . ?
C16 C15 C3 117.23(13) . . ?
C20 C15 C3 123.63(14) . . ?
C17 C16 C15 120.27(15) . . ?
F1 C17 C16 120.41(15) . . ?
F1 C17 C18 119.14(14) . . ?
C16 C17 C18 120.45(15) . . ?
F2 C18 C19 120.30(15) . . ?
F2 C18 C17 119.22(15) . . ?
C19 C18 C17 120.47(15) . . ?
C18 C19 C20 120.34(15) . . ?
C19 C20 C15 119.29(14) . . ?
C19 C20 C23 116.67(14) . . ?
C15 C20 C23 124.02(14) . . ?
C23 C22 C21 130.17(15) . . ?
C23 C22 S2 108.41(12) . . ?
C21 C22 S2 121.41(12) . . ?
C22 C23 N2 115.91(14) . . ?
C22 C23 C20 127.95(14) . . ?
N2 C23 C20 116.14(13) . . ?
N2 C24 C25 126.18(14) . . ?
N2 C24 S2 113.80(11) . . ?
C25 C24 S2 120.02(12) . . ?
C30 C25 C26 120.67(14) . . ?
C30 C25 C24 115.60(14) . . ?
C26 C25 C24 123.73(14) . . ?
C27 C26 C25 116.06(14) . . ?
C27 C26 C31 119.46(14) . . ?
C25 C26 C31 124.47(14) . . ?
C28 C27 C26 122.88(15) . . ?
C29 C28 C27 120.19(15) . . ?
C28 C29 C30 118.65(15) . . ?
C29 C30 C25 121.46(15) . . ?
C33 C31 C26 109.20(13) . . ?
C33 C31 C32 109.77(14) . . ?
C26 C31 C32 112.84(13) . . ?
C33 C31 C34 107.57(14) . . ?
C26 C31 C34 110.74(13) . . ?
C32 C31 C34 106.57(13) . . ?
C4 S1 C2 90.50(7) . . ?
C24 S2 C22 90.53(8) . . ?
C4 N1 C3 110.88(13) . . ?
C24 N2 C23 111.21(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 N1 -178.65(15) . . . . ?
S1 C2 C3 N1 1.12(17) . . . . ?
C1 C2 C3 C15 2.5(3) . . . . ?
S1 C2 C3 C15 -177.78(13) . . . . ?
N1 C4 C5 C10 95.83(19) . . . . ?
S1 C4 C5 C10 -76.68(17) . . . . ?
N1 C4 C5 C6 -80.6(2) . . . . ?
S1 C4 C5 C6 106.91(16) . . . . ?
C10 C5 C6 C7 -4.9(2) . . . . ?
C4 C5 C6 C7 171.29(14) . . . . ?
C10 C5 C6 C11 177.81(14) . . . . ?
C4 C5 C6 C11 -6.0(2) . . . . ?
C5 C6 C7 C8 2.9(2) . . . . ?
C11 C6 C7 C8 -179.70(15) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 -2.5(3) . . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
C6 C5 C10 C9 3.5(2) . . . . ?
C4 C5 C10 C9 -173.09(15) . . . . ?
C7 C6 C11 C12 148.09(15) . . . . ?
C5 C6 C11 C12 -34.7(2) . . . . ?
C7 C6 C11 C13 -90.44(18) . . . . ?
C5 C6 C11 C13 86.75(18) . . . . ?
C7 C6 C11 C14 29.3(2) . . . . ?
C5 C6 C11 C14 -153.54(15) . . . . ?
C2 C3 C15 C16 -131.57(17) . . . . ?
N1 C3 C15 C16 49.54(19) . . . . ?
C2 C3 C15 C20 49.3(2) . . . . ?
N1 C3 C15 C20 -129.61(15) . . . . ?
C20 C15 C16 C17 -1.6(2) . . . . ?
C3 C15 C16 C17 179.19(14) . . . . ?
C15 C16 C17 F1 -179.76(13) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
F1 C17 C18 F2 -0.6(2) . . . . ?
C16 C17 C18 F2 179.53(14) . . . . ?
F1 C17 C18 C19 -179.53(14) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
F2 C18 C19 C20 -178.71(14) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 C15 -1.7(2) . . . . ?
C18 C19 C20 C23 179.55(14) . . . . ?
C16 C15 C20 C19 2.4(2) . . . . ?
C3 C15 C20 C19 -178.47(14) . . . . ?
C16 C15 C20 C23 -178.98(14) . . . . ?
C3 C15 C20 C23 0.2(2) . . . . ?
C21 C22 C23 N2 -174.81(16) . . . . ?
S2 C22 C23 N2 3.86(18) . . . . ?
C21 C22 C23 C20 4.4(3) . . . . ?
S2 C22 C23 C20 -176.90(13) . . . . ?
C19 C20 C23 C22 -132.54(17) . . . . ?
C15 C20 C23 C22 48.8(2) . . . . ?
C19 C20 C23 N2 46.70(19) . . . . ?
C15 C20 C23 N2 -131.95(15) . . . . ?
N2 C24 C25 C30 110.85(18) . . . . ?
S2 C24 C25 C30 -68.96(17) . . . . ?
N2 C24 C25 C26 -68.4(2) . . . . ?
S2 C24 C25 C26 111.77(15) . . . . ?
C30 C25 C26 C27 -3.1(2) . . . . ?
C24 C25 C26 C27 176.10(14) . . . . ?
C30 C25 C26 C31 178.24(14) . . . . ?
C24 C25 C26 C31 -2.5(2) . . . . ?
C25 C26 C27 C28 1.1(2) . . . . ?
C31 C26 C27 C28 179.75(15) . . . . ?
C26 C27 C28 C29 1.4(3) . . . . ?
C27 C28 C29 C30 -1.7(3) . . . . ?
C28 C29 C30 C25 -0.4(3) . . . . ?
C26 C25 C30 C29 2.9(2) . . . . ?
C24 C25 C30 C29 -176.38(15) . . . . ?
C27 C26 C31 C33 -99.42(17) . . . . ?
C25 C26 C31 C33 79.14(18) . . . . ?
C27 C26 C31 C32 138.21(15) . . . . ?
C25 C26 C31 C32 -43.2(2) . . . . ?
C27 C26 C31 C34 18.8(2) . . . . ?
C25 C26 C31 C34 -162.58(14) . . . . ?
N1 C4 S1 C2 0.78(13) . . . . ?
C5 C4 S1 C2 174.04(13) . . . . ?
C3 C2 S1 C4 -1.03(12) . . . . ?
C1 C2 S1 C4 178.77(14) . . . . ?
N2 C24 S2 C22 2.54(13) . . . . ?
C25 C24 S2 C22 -177.63(13) . . . . ?
C23 C22 S2 C24 -3.46(13) . . . . ?
C21 C22 S2 C24 175.35(15) . . . . ?
C5 C4 N1 C3 -173.21(14) . . . . ?
S1 C4 N1 C3 -0.28(17) . . . . ?
C2 C3 N1 C4 -0.58(19) . . . . ?
C15 C3 N1 C4 178.45(13) . . . . ?
C25 C24 N2 C23 179.37(14) . . . . ?
S2 C24 N2 C23 -0.81(17) . . . . ?
C22 C23 N2 C24 -2.1(2) . . . . ?
C20 C23 N2 C24 178.59(13) . . . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.052


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_3o
_database_code_depnum_ccdc_archive 'CCDC 2452876'
loop_
_audit_author_name
_audit_author_address
'Daichi Kitagawa'
;Osaka Metropolitan University
Japan
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2025-06-09 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         'C30 H26 F2 N2 S2'
_chemical_formula_sum            'C30 H26 F2 N2 S2'
_chemical_formula_weight         516.65

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'
N N 0.0311 0.0180 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.4157(5)
_cell_length_b                   10.96810(10)
_cell_length_c                   13.8257(3)
_cell_angle_alpha                90
_cell_angle_beta                 121.068(3)
_cell_angle_gamma                90
_cell_volume                     2521.89(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    10816
_cell_measurement_theta_min      4.8110
_cell_measurement_theta_max      79.6640

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.220
_shelx_estimated_absorpt_T_min   0.665
_shelx_estimated_absorpt_T_max   0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            16622
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.830
_diffrn_reflns_theta_max         79.614
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2677
_reflns_number_gt                2552
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_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)+(0.0338P)²+2.7746P] 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         2677
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.32441(9) 0.58597(13) -0.03680(11) 0.0258(3) Uani 1 1 d . . . . .
H1 H 0.3567 0.6603 -0.0198 0.039 Uiso 1 1 calc R U . . .
H1A H 0.2675 0.6078 -0.0722 0.039 Uiso 1 1 calc R U . . .
H1B H 0.3321 0.5347 -0.0885 0.039 Uiso 1 1 calc R U . . .
C2 C 0.35032(7) 0.51754(12) 0.07016(11) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.40957(7) 0.54261(11) 0.17894(10) 0.0161(2) Uani 1 1 d . . . . .
C4 C 0.36943(7) 0.36719(11) 0.21368(10) 0.0161(2) Uani 1 1 d . . . . .
C5 C 0.35996(8) 0.26315(11) 0.27380(10) 0.0174(2) Uani 1 1 d . . . . .
C6 C 0.42581(8) 0.20602(11) 0.36632(11) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.40977(9) 0.11190(12) 0.42018(12) 0.0241(3) Uani 1 1 d . . . . .
H7 H 0.4535 0.0731 0.4836 0.029 Uiso 1 1 calc R U . . .
C8 C 0.33224(10) 0.07325(13) 0.38418(13) 0.0276(3) Uani 1 1 d . . . . .
H8 H 0.3234 0.0091 0.4227 0.033 Uiso 1 1 calc R U . . .
C9 C 0.26747(9) 0.12855(13) 0.29167(12) 0.0262(3) Uani 1 1 d . . . . .
H9 H 0.2141 0.1021 0.2660 0.031 Uiso 1 1 calc R U . . .
C10 C 0.28152(8) 0.22284(13) 0.23716(11) 0.0215(3) Uani 1 1 d . . . . .
H10 H 0.2373 0.2609 0.1739 0.026 Uiso 1 1 calc R U . . .
C11 C 0.51247(8) 0.24153(12) 0.41302(11) 0.0203(3) Uani 1 1 d . . . . .
H11 H 0.5167 0.2908 0.3563 0.024 Uiso 1 1 calc R U . . .
H11A H 0.5453 0.1670 0.4280 0.024 Uiso 1 1 calc R U . . .
C12 C 0.54536(9) 0.31475(15) 0.52191(12) 0.0279(3) Uani 1 1 d . . . . .
H12 H 0.5155 0.3915 0.5061 0.042 Uiso 1 1 calc R U . . .
H12A H 0.6024 0.3324 0.5524 0.042 Uiso 1 1 calc R U . . .
H12B H 0.5392 0.2675 0.5772 0.042 Uiso 1 1 calc R U . . .
C13 C 0.45779(8) 0.65629(11) 0.21539(10) 0.0164(2) Uani 1 1 d . . . . .
C14 C 0.41705(8) 0.76783(12) 0.18183(11) 0.0205(3) Uani 1 1 d . . . . .
H14 H 0.3601 0.7688 0.1351 0.025 Uiso 1 1 calc R U . . .
C15 C 0.45880(9) 0.87629(12) 0.21592(12) 0.0237(3) Uani 1 1 d . . . . .
N1 N 0.42026(6) 0.45725(9) 0.25959(9) 0.0156(2) Uani 1 1 d . . . . .
S1 S 0.30602(2) 0.38058(3) 0.06784(2) 0.01832(10) Uani 1 1 d . . . . .
F1 F 0.41878(6) 0.98330(7) 0.18271(8) 0.0342(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
C1 C2 1.4951(18) . ?
C2 C3 1.3694(18) . ?
C2 S1 1.7231(13) . ?
C3 N1 1.3872(16) . ?
C3 C13 1.4826(17) . ?
C4 N1 1.3061(16) . ?
C4 C5 1.4780(17) . ?
C4 S1 1.7438(13) . ?
C5 C6 1.4056(19) . ?
C5 C10 1.4054(18) . ?
C6 C7 1.3988(18) . ?
C6 C11 1.5095(18) . ?
C7 C8 1.386(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.3871(19) . ?
C11 C12 1.5255(19) . ?
C13 C14 1.3996(17) . ?
C14 C15 1.378(2) . ?
C15 F1 1.3506(15) . ?

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
C3 C2 C1 130.44(12) . . ?
C3 C2 S1 108.90(9) . . ?
C1 C2 S1 120.62(10) . . ?
C2 C3 N1 116.09(11) . . ?
C2 C3 C13 124.57(11) . . ?
N1 C3 C13 119.21(11) . . ?
N1 C4 C5 126.35(11) . . ?
N1 C4 S1 113.81(9) . . ?
C5 C4 S1 119.78(9) . . ?
C6 C5 C10 119.69(12) . . ?
C6 C5 C4 122.50(11) . . ?
C10 C5 C4 117.80(12) . . ?
C7 C6 C5 117.76(12) . . ?
C7 C6 C11 117.91(12) . . ?
C5 C6 C11 124.32(11) . . ?
C8 C7 C6 122.24(13) . . ?
C7 C8 C9 119.82(13) . . ?
C10 C9 C8 119.21(13) . . ?
C9 C10 C5 121.27(13) . . ?
C6 C11 C12 111.37(11) . . ?
C14 C13 C3 118.21(11) . . ?
C15 C14 C13 120.60(13) . . ?
F1 C15 C14 120.01(13) . . ?
C4 N1 C3 110.96(10) . . ?
C2 S1 C4 90.24(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 N1 -177.83(13) . . . . ?
S1 C2 C3 N1 -0.35(14) . . . . ?
C1 C2 C3 C13 6.3(2) . . . . ?
S1 C2 C3 C13 -176.18(10) . . . . ?
N1 C4 C5 C6 -39.02(19) . . . . ?
S1 C4 C5 C6 143.82(10) . . . . ?
N1 C4 C5 C10 139.66(13) . . . . ?
S1 C4 C5 C10 -37.50(15) . . . . ?
C10 C5 C6 C7 -1.48(18) . . . . ?
C4 C5 C6 C7 177.18(11) . . . . ?
C10 C5 C6 C11 -179.95(12) . . . . ?
C4 C5 C6 C11 -1.30(19) . . . . ?
C5 C6 C7 C8 1.0(2) . . . . ?
C11 C6 C7 C8 179.57(13) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
C8 C9 C10 C5 0.1(2) . . . . ?
C6 C5 C10 C9 0.98(19) . . . . ?
C4 C5 C10 C9 -177.73(12) . . . . ?
C7 C6 C11 C12 -75.02(15) . . . . ?
C5 C6 C11 C12 103.45(15) . . . . ?
C2 C3 C13 C14 49.88(17) . . . . ?
N1 C3 C13 C14 -125.84(12) . . . . ?
C2 C3 C13 C13 -131.95(16) . . . 2_655 ?
N1 C3 C13 C13 52.34(19) . . . 2_655 ?
C13 C13 C14 C15 0.0(2) 2_655 . . . ?
C3 C13 C14 C15 178.23(12) . . . . ?
C13 C14 C15 F1 179.84(11) . . . . ?
C13 C14 C15 C15 -0.4(2) . . . 2_655 ?
C5 C4 N1 C3 -176.47(11) . . . . ?
S1 C4 N1 C3 0.83(13) . . . . ?
C2 C3 N1 C4 -0.31(15) . . . . ?
C13 C3 N1 C4 175.76(11) . . . . ?
C3 C2 S1 C4 0.66(10) . . . . ?
C1 C2 S1 C4 178.43(11) . . . . ?
N1 C4 S1 C2 -0.89(10) . . . . ?
C5 C4 S1 C2 176.61(10) . . . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.047


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_6o
_database_code_depnum_ccdc_archive 'CCDC 2452879'
loop_
_audit_author_name
_audit_author_address
'Daichi Kitagawa'
;Osaka Metropolitan University
Japan
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2025-06-09 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         'C30 H26 F2 N2 S2'
_chemical_formula_sum            'C30 H26 F2 N2 S2'
_chemical_formula_weight         516.65

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

_cell_length_a                   21.4133(3)
_cell_length_b                   13.7635(2)
_cell_length_c                   8.96300(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2641.59(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    6382
_cell_measurement_theta_min      3.8060
_cell_measurement_theta_max      77.1240

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.119
_shelx_estimated_absorpt_T_min   0.363
_shelx_estimated_absorpt_T_max   0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            9817
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.818
_diffrn_reflns_theta_max         77.342
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2712
_reflns_number_gt                2491
_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       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_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)+(0.0531P)²+1.0188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2712
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 -0.06160(6) 0.30984(11) 0.45763(16) 0.0234(3) Uani 1 1 d . . . . .
H1 H -0.0760 0.3615 0.3907 0.035 Uiso 1 1 calc R U . . .
H2 H -0.0738 0.3254 0.5603 0.035 Uiso 1 1 calc R U . . .
H3 H -0.0806 0.2480 0.4280 0.035 Uiso 1 1 calc R U . . .
C2 C 0.00808(6) 0.30178(10) 0.44830(14) 0.0185(3) Uani 1 1 d . . . . .
C3 C 0.04461(6) 0.23235(9) 0.38289(14) 0.0170(3) Uani 1 1 d . . . . .
C4 C 0.12139(6) 0.32190(10) 0.47618(13) 0.0171(3) Uani 1 1 d . . . . .
C5 C 0.18583(6) 0.35408(10) 0.51304(14) 0.0177(3) Uani 1 1 d . . . . .
C6 C 0.22052(6) 0.29992(10) 0.61646(15) 0.0214(3) Uani 1 1 d . . . . .
C7 C 0.28142(7) 0.32983(11) 0.64890(16) 0.0264(3) Uani 1 1 d . . . . .
H4 H 0.3058 0.2936 0.7179 0.032 Uiso 1 1 calc R U . . .
C8 C 0.30664(7) 0.41140(12) 0.58193(17) 0.0279(3) Uani 1 1 d . . . . .
H5 H 0.3480 0.4311 0.6057 0.033 Uiso 1 1 calc R U . . .
C9 C 0.27182(7) 0.46454(11) 0.48013(16) 0.0246(3) Uani 1 1 d . . . . .
H6 H 0.2895 0.5204 0.4345 0.029 Uiso 1 1 calc R U . . .
C10 C 0.21091(6) 0.43670(10) 0.44394(15) 0.0198(3) Uani 1 1 d . . . . .
C11 C 0.17523(7) 0.49348(12) 0.32868(17) 0.0289(3) Uani 1 1 d . . . . .
H7 H 0.1612 0.4496 0.2494 0.043 Uiso 1 1 calc R U . . .
H8 H 0.2023 0.5437 0.2860 0.043 Uiso 1 1 calc R U . . .
H9 H 0.1389 0.5242 0.3755 0.043 Uiso 1 1 calc R U . . .
C12 C 0.19314(8) 0.21323(11) 0.69552(17) 0.0305(3) Uani 1 1 d . . . . .
H10 H 0.1949 0.1564 0.6297 0.046 Uiso 1 1 calc R U . . .
H11 H 0.1496 0.2267 0.7218 0.046 Uiso 1 1 calc R U . . .
H12 H 0.2171 0.2001 0.7865 0.046 Uiso 1 1 calc R U . . .
C13 C 0.02257(6) 0.14291(9) 0.30698(14) 0.0173(3) Uani 1 1 d . . . . .
C14 C 0.04663(7) 0.05421(10) 0.35776(16) 0.0211(3) Uani 1 1 d . . . . .
H13 H 0.0787 0.0535 0.4309 0.025 Uiso 1 1 calc R U . . .
C15 C 0.02377(7) -0.03187(10) 0.30184(16) 0.0229(3) Uani 1 1 d . . . . .
S1 S 0.05582(2) 0.38593(2) 0.53460(4) 0.02042(12) Uani 1 1 d . . . . .
F1 F 0.04668(4) -0.11743(6) 0.35092(11) 0.0316(2) Uani 1 1 d . . . . .
N1 N 0.10850(5) 0.24369(8) 0.40100(12) 0.0174(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
C1 C2 1.4986(18) . ?
C2 C3 1.3669(19) . ?
C2 S1 1.7276(13) . ?
C3 N1 1.3866(17) . ?
C3 C13 1.4836(18) . ?
C4 N1 1.2996(18) . ?
C4 C5 1.4864(17) . ?
C4 S1 1.7385(13) . ?
C5 C10 1.4017(19) . ?
C5 C6 1.4023(19) . ?
C6 C7 1.398(2) . ?
C6 C12 1.507(2) . ?
C7 C8 1.383(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.3977(19) . ?
C10 C11 1.5039(19) . ?
C13 C14 1.4010(19) . ?
C13 C13 1.406(3) 4 ?
C14 C15 1.376(2) . ?
C15 F1 1.3494(15) . ?
C15 C15 1.378(3) 4 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 130.20(13) . . ?
C3 C2 S1 108.79(10) . . ?
C1 C2 S1 120.96(10) . . ?
C2 C3 N1 115.83(12) . . ?
C2 C3 C13 126.49(12) . . ?
N1 C3 C13 117.45(11) . . ?
N1 C4 C5 124.00(12) . . ?
N1 C4 S1 113.86(10) . . ?
C5 C4 S1 122.12(10) . . ?
C10 C5 C6 121.36(12) . . ?
C10 C5 C4 119.94(12) . . ?
C6 C5 C4 118.70(12) . . ?
C7 C6 C5 118.36(13) . . ?
C7 C6 C12 119.89(13) . . ?
C5 C6 C12 121.72(12) . . ?
C8 C7 C6 120.87(13) . . ?
C7 C8 C9 120.25(13) . . ?
C8 C9 C10 120.65(14) . . ?
C9 C10 C5 118.51(13) . . ?
C9 C10 C11 119.41(13) . . ?
C5 C10 C11 122.04(12) . . ?
C14 C13 C13 119.25(8) . 4 ?
C14 C13 C3 117.20(11) . . ?
C13 C13 C3 123.49(7) 4 . ?
C15 C14 C13 120.06(13) . . ?
F1 C15 C14 120.21(13) . . ?
F1 C15 C15 119.23(8) . 4 ?
C14 C15 C15 120.54(8) . 4 ?
C2 S1 C4 90.18(6) . . ?
C4 N1 C3 111.31(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 N1 -176.73(13) . . . . ?
S1 C2 C3 N1 0.73(14) . . . . ?
C1 C2 C3 C13 -2.4(2) . . . . ?
S1 C2 C3 C13 175.05(10) . . . . ?
N1 C4 C5 C10 109.95(15) . . . . ?
S1 C4 C5 C10 -71.40(15) . . . . ?
N1 C4 C5 C6 -69.58(17) . . . . ?
S1 C4 C5 C6 109.07(13) . . . . ?
C10 C5 C6 C7 -0.4(2) . . . . ?
C4 C5 C6 C7 179.07(12) . . . . ?
C10 C5 C6 C12 177.70(13) . . . . ?
C4 C5 C6 C12 -2.78(19) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C12 C6 C7 C8 -177.50(13) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C9 C10 C5 0.1(2) . . . . ?
C8 C9 C10 C11 -177.61(13) . . . . ?
C6 C5 C10 C9 0.05(19) . . . . ?
C4 C5 C10 C9 -179.47(12) . . . . ?
C6 C5 C10 C11 177.73(13) . . . . ?
C4 C5 C10 C11 -1.79(19) . . . . ?
C2 C3 C13 C14 -124.82(15) . . . . ?
N1 C3 C13 C14 49.42(16) . . . . ?
C2 C3 C13 C13 52.3(2) . . . 4 ?
N1 C3 C13 C13 -133.44(16) . . . 4 ?
C13 C13 C14 C15 -3.4(2) 4 . . . ?
C3 C13 C14 C15 173.88(12) . . . . ?
C13 C14 C15 F1 -179.76(12) . . . . ?
C13 C14 C15 C15 -1.4(2) . . . 4 ?
C3 C2 S1 C4 0.13(10) . . . . ?
C1 C2 S1 C4 177.87(12) . . . . ?
N1 C4 S1 C2 -1.02(10) . . . . ?
C5 C4 S1 C2 -179.80(11) . . . . ?
C5 C4 N1 C3 -179.67(12) . . . . ?
S1 C4 N1 C3 1.58(14) . . . . ?
C2 C3 N1 C4 -1.52(16) . . . . ?
C13 C3 N1 C4 -176.37(11) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.056


_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_7o
_database_code_depnum_ccdc_archive 'CCDC 2452880'
loop_
_audit_author_name
_audit_author_address
'Daichi Kitagawa'
;Osaka Metropolitan University
Japan
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2025-06-09 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         'C44 H54 F2 N2 S2'
_chemical_formula_sum            'C44 H54 F2 N2 S2'
_chemical_formula_weight         713.01

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.6733(3)
_cell_length_b                   13.4099(3)
_cell_length_c                   13.5210(3)
_cell_angle_alpha                76.6459(18)
_cell_angle_beta                 74.5390(19)
_cell_angle_gamma                85.3589(19)
_cell_volume                     1984.37(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    17328
_cell_measurement_theta_min      3.4580
_cell_measurement_theta_max      77.2750

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             764
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.539
_shelx_estimated_absorpt_T_min   0.615
_shelx_estimated_absorpt_T_max   0.748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            26282
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.388
_diffrn_reflns_theta_max         77.577
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8121
_reflns_number_gt                7407
_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       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_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)+(0.0399P)²+0.5842P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8121
_refine_ls_number_parameters     465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
F1 F 0.35517(7) -0.02084(6) 0.16246(5) 0.02478(16) Uani 1 1 d . . . . .
F2 F 0.22244(7) -0.17368(5) 0.30032(6) 0.02407(16) Uani 1 1 d . . . . .
N1 N 0.34563(9) 0.25789(7) 0.36684(7) 0.01630(19) Uani 1 1 d . . . . .
N2 N 0.15547(9) -0.08105(7) 0.66071(7) 0.01665(19) Uani 1 1 d . . . . .
S1 S 0.44571(3) 0.27050(2) 0.51015(2) 0.01916(8) Uani 1 1 d . . . . .
S2 S 0.02943(2) 0.05729(2) 0.74528(2) 0.01803(7) Uani 1 1 d . . . . .
C1 C 0.40723(11) 0.06186(9) 0.59969(9) 0.0205(2) Uani 1 1 d . . . . .
H1 H 0.3984 -0.0013 0.5780 0.031 Uiso 1 1 calc R U . . .
H2 H 0.3467 0.0651 0.6649 0.031 Uiso 1 1 calc R U . . .
H3 H 0.4865 0.0625 0.6114 0.031 Uiso 1 1 calc R U . . .
C2 C 0.39210(10) 0.15258(9) 0.51524(9) 0.0173(2) Uani 1 1 d . . . . .
C3 C 0.34200(10) 0.16135(9) 0.43287(9) 0.0156(2) Uani 1 1 d . . . . .
C4 C 0.39668(10) 0.32331(9) 0.39817(9) 0.0171(2) Uani 1 1 d . . . . .
C5 C 0.42292(10) 0.43188(9) 0.34425(9) 0.0167(2) Uani 1 1 d . . . . .
C6 C 0.51366(11) 0.45261(9) 0.24998(9) 0.0182(2) Uani 1 1 d . . . . .
C7 C 0.54536(11) 0.55403(9) 0.20495(9) 0.0191(2) Uani 1 1 d . . . . .
H4 H 0.6050 0.5688 0.1405 0.023 Uiso 1 1 calc R U . . .
C8 C 0.49233(10) 0.63457(9) 0.25138(9) 0.0173(2) Uani 1 1 d . . . . .
C9 C 0.40087(10) 0.61222(9) 0.34268(9) 0.0172(2) Uani 1 1 d . . . . .
H5 H 0.3621 0.6668 0.3736 0.021 Uiso 1 1 calc R U . . .
C10 C 0.36420(10) 0.51201(9) 0.39038(9) 0.0167(2) Uani 1 1 d . . . . .
C11 C 0.26245(10) 0.49365(9) 0.48993(9) 0.0185(2) Uani 1 1 d . . . . .
H6 H 0.2420 0.4195 0.5079 0.022 Uiso 1 1 calc R U . . .
C12 C 0.29898(12) 0.51695(11) 0.58235(10) 0.0258(3) Uani 1 1 d . . . . .
H7 H 0.3165 0.5899 0.5677 0.039 Uiso 1 1 calc R U . . .
H8 H 0.3699 0.4759 0.5926 0.039 Uiso 1 1 calc R U . . .
H9 H 0.2340 0.5000 0.6462 0.039 Uiso 1 1 calc R U . . .
C13 C 0.15185(12) 0.55685(12) 0.47240(11) 0.0319(3) Uani 1 1 d . . . . .
H10 H 0.1283 0.5397 0.4141 0.048 Uiso 1 1 calc R U . . .
H11 H 0.1695 0.6300 0.4554 0.048 Uiso 1 1 calc R U . . .
H12 H 0.0869 0.5414 0.5364 0.048 Uiso 1 1 calc R U . . .
C14 C 0.53522(11) 0.74348(9) 0.20467(9) 0.0194(2) Uani 1 1 d . . . . .
H13 H 0.4896 0.7879 0.2525 0.023 Uiso 1 1 calc R U . . .
C15 C 0.66743(12) 0.75020(10) 0.19902(10) 0.0252(3) Uani 1 1 d . . . . .
H14 H 0.7151 0.7137 0.1464 0.038 Uiso 1 1 calc R U . . .
H15 H 0.6816 0.7189 0.2679 0.038 Uiso 1 1 calc R U . . .
H16 H 0.6902 0.8223 0.1792 0.038 Uiso 1 1 calc R U . . .
C16 C 0.51055(13) 0.78400(10) 0.09662(10) 0.0256(3) Uani 1 1 d . . . . .
H17 H 0.4252 0.7808 0.1030 0.038 Uiso 1 1 calc R U . . .
H18 H 0.5547 0.7419 0.0479 0.038 Uiso 1 1 calc R U . . .
H19 H 0.5359 0.8552 0.0697 0.038 Uiso 1 1 calc R U . . .
C17 C 0.57871(11) 0.36787(9) 0.19749(10) 0.0214(2) Uani 1 1 d . . . . .
H20 H 0.5537 0.3007 0.2466 0.026 Uiso 1 1 calc R U . . .
C18 C 0.71326(13) 0.37398(11) 0.17632(12) 0.0314(3) Uani 1 1 d . . . . .
H21 H 0.7408 0.4374 0.1250 0.047 Uiso 1 1 calc R U . . .
H22 H 0.7514 0.3149 0.1484 0.047 Uiso 1 1 calc R U . . .
H23 H 0.7341 0.3736 0.2420 0.047 Uiso 1 1 calc R U . . .
C19 C 0.54315(14) 0.37048(12) 0.09623(12) 0.0351(3) Uani 1 1 d . . . . .
H24 H 0.5830 0.3137 0.0651 0.053 Uiso 1 1 calc R U . . .
H25 H 0.5667 0.4357 0.0466 0.053 Uiso 1 1 calc R U . . .
H26 H 0.4568 0.3637 0.1120 0.053 Uiso 1 1 calc R U . . .
C20 C 0.29672(10) 0.07606(8) 0.40200(9) 0.0154(2) Uani 1 1 d . . . . .
C21 C 0.34000(10) 0.06930(9) 0.29633(9) 0.0170(2) Uani 1 1 d . . . . .
H27 H 0.3880 0.1220 0.2474 0.020 Uiso 1 1 calc R U . . .
C22 C 0.31297(10) -0.01348(9) 0.26361(9) 0.0183(2) Uani 1 1 d . . . . .
C23 C 0.24495(11) -0.09180(9) 0.33458(10) 0.0186(2) Uani 1 1 d . . . . .
C24 C 0.19888(11) -0.08577(9) 0.43774(9) 0.0191(2) Uani 1 1 d . . . . .
H28 H 0.1518 -0.1397 0.4857 0.023 Uiso 1 1 calc R U . . .
C25 C 0.22124(10) -0.00014(9) 0.47248(9) 0.0164(2) Uani 1 1 d . . . . .
C26 C 0.07795(11) 0.19443(9) 0.54802(9) 0.0205(2) Uani 1 1 d . . . . .
H29 H 0.0893 0.1909 0.4744 0.031 Uiso 1 1 calc R U . . .
H30 H 0.1359 0.2409 0.5527 0.031 Uiso 1 1 calc R U . . .
H31 H -0.0027 0.2200 0.5752 0.031 Uiso 1 1 calc R U . . .
C27 C 0.09516(10) 0.08973(9) 0.61176(9) 0.0171(2) Uani 1 1 d . . . . .
C28 C 0.15820(10) 0.00640(9) 0.58173(9) 0.0160(2) Uani 1 1 d . . . . .
C29 C 0.09239(10) -0.06517(9) 0.75132(9) 0.0162(2) Uani 1 1 d . . . . .
C30 C 0.07622(10) -0.14181(8) 0.85289(9) 0.0157(2) Uani 1 1 d . . . . .
C31 C 0.00042(10) -0.22511(9) 0.87397(9) 0.0176(2) Uani 1 1 d . . . . .
C32 C -0.00825(11) -0.29838(9) 0.96755(9) 0.0194(2) Uani 1 1 d . . . . .
H32 H -0.0586 -0.3550 0.9823 0.023 Uiso 1 1 calc R U . . .
C33 C 0.05428(11) -0.29132(9) 1.03992(9) 0.0193(2) Uani 1 1 d . . . . .
C34 C 0.12598(11) -0.20660(9) 1.01822(9) 0.0186(2) Uani 1 1 d . . . . .
H33 H 0.1676 -0.2000 1.0679 0.022 Uiso 1 1 calc R U . . .
C35 C 0.13840(10) -0.13125(9) 0.92572(9) 0.0166(2) Uani 1 1 d . . . . .
C36 C 0.22113(10) -0.04246(9) 0.90619(9) 0.0175(2) Uani 1 1 d . . . . .
H34 H 0.2120 0.0069 0.8408 0.021 Uiso 1 1 calc R U . . .
C37 C 0.18622(13) 0.01470(11) 0.99586(10) 0.0285(3) Uani 1 1 d . . . . .
H35 H 0.1898 -0.0328 1.0620 0.043 Uiso 1 1 calc R U . . .
H36 H 0.1052 0.0428 1.0014 0.043 Uiso 1 1 calc R U . . .
H37 H 0.2413 0.0707 0.9816 0.043 Uiso 1 1 calc R U . . .
C38 C 0.35073(12) -0.07932(11) 0.88656(12) 0.0298(3) Uani 1 1 d . . . . .
H38 H 0.3697 -0.1150 0.8284 0.045 Uiso 1 1 calc R U . . .
H39 H 0.3633 -0.1263 0.9502 0.045 Uiso 1 1 calc R U . . .
H40 H 0.4025 -0.0203 0.8685 0.045 Uiso 1 1 calc R U . . .
C39 C 0.04514(12) -0.37424(9) 1.13970(9) 0.0233(3) Uani 1 1 d . . . . .
H41 H -0.0079 -0.4285 1.1381 0.028 Uiso 1 1 calc R U . . .
C40 C -0.01078(13) -0.33213(11) 1.23801(10) 0.0286(3) Uani 1 1 d . . . . .
H42 H -0.0862 -0.2968 1.2316 0.043 Uiso 1 1 calc R U . . .
H43 H 0.0434 -0.2838 1.2454 0.043 Uiso 1 1 calc R U . . .
H44 H -0.0254 -0.3888 1.3000 0.043 Uiso 1 1 calc R U . . .
C41 C 0.16598(14) -0.42429(11) 1.14530(11) 0.0335(3) Uani 1 1 d . . . . .
H45 H 0.2191 -0.3731 1.1492 0.050 Uiso 1 1 calc R U . . .
H46 H 0.2003 -0.4518 1.0823 0.050 Uiso 1 1 calc R U . . .
H47 H 0.1562 -0.4801 1.2079 0.050 Uiso 1 1 calc R U . . .
C42 C -0.06842(11) -0.23758(9) 0.79669(9) 0.0198(2) Uani 1 1 d . . . . .
H48 H -0.0727 -0.1691 0.7488 0.024 Uiso 1 1 calc R U . . .
C43 C -0.00153(12) -0.31172(10) 0.72871(10) 0.0258(3) Uani 1 1 d . . . . .
H49 H 0.0095 -0.3783 0.7741 0.039 Uiso 1 1 calc R U . . .
H50 H 0.0763 -0.2838 0.6881 0.039 Uiso 1 1 calc R U . . .
H51 H -0.0476 -0.3204 0.6805 0.039 Uiso 1 1 calc R U . . .
C44 C -0.19619(12) -0.27219(11) 0.85104(11) 0.0271(3) Uani 1 1 d . . . . .
H52 H -0.2370 -0.2239 0.8940 0.041 Uiso 1 1 calc R U . . .
H53 H -0.1948 -0.3408 0.8960 0.041 Uiso 1 1 calc R U . . .
H54 H -0.2384 -0.2740 0.7978 0.041 Uiso 1 1 calc R U . . .


_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
F1 C22 1.3484(13) . ?
F2 C23 1.3548(13) . ?
N1 C4 1.3019(15) . ?
N1 C3 1.3891(14) . ?
N2 C29 1.3049(15) . ?
N2 C28 1.3879(14) . ?
S1 C2 1.7274(12) . ?
S1 C4 1.7386(12) . ?
S2 C27 1.7292(11) . ?
S2 C29 1.7373(12) . ?
C1 C2 1.4987(16) . ?
C2 C3 1.3682(16) . ?
C3 C20 1.4824(16) . ?
C4 C5 1.4858(16) . ?
C5 C10 1.4057(16) . ?
C5 C6 1.4100(16) . ?
C6 C7 1.3914(16) . ?
C6 C17 1.5222(16) . ?
C7 C8 1.3934(17) . ?
C8 C9 1.3899(16) . ?
C8 C14 1.5186(15) . ?
C9 C10 1.3966(16) . ?
C10 C11 1.5249(16) . ?
C11 C12 1.5254(17) . ?
C11 C13 1.5279(18) . ?
C14 C16 1.5312(17) . ?
C14 C15 1.5338(17) . ?
C17 C18 1.5251(19) . ?
C17 C19 1.5254(19) . ?
C20 C21 1.4044(16) . ?
C20 C25 1.4060(16) . ?
C21 C22 1.3731(17) . ?
C22 C23 1.3847(17) . ?
C23 C24 1.3735(17) . ?
C24 C25 1.4037(16) . ?
C25 C28 1.4837(16) . ?
C26 C27 1.4973(16) . ?
C27 C28 1.3683(16) . ?
C29 C30 1.4896(15) . ?
C30 C35 1.4066(16) . ?
C30 C31 1.4109(16) . ?
C31 C32 1.3965(16) . ?
C31 C42 1.5218(16) . ?
C32 C33 1.3907(17) . ?
C33 C34 1.3951(17) . ?
C33 C39 1.5224(16) . ?
C34 C35 1.3963(16) . ?
C35 C36 1.5248(16) . ?
C36 C38 1.5261(17) . ?
C36 C37 1.5293(17) . ?
C39 C41 1.525(2) . ?
C39 C40 1.5285(18) . ?
C42 C44 1.5330(17) . ?
C42 C43 1.5352(17) . ?

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
C4 N1 C3 111.31(10) . . ?
C29 N2 C28 111.10(10) . . ?
C2 S1 C4 90.42(6) . . ?
C27 S2 C29 90.34(5) . . ?
C3 C2 C1 131.00(11) . . ?
C3 C2 S1 108.66(8) . . ?
C1 C2 S1 120.33(9) . . ?
C2 C3 N1 115.89(10) . . ?
C2 C3 C20 126.05(10) . . ?
N1 C3 C20 117.72(10) . . ?
N1 C4 C5 126.71(10) . . ?
N1 C4 S1 113.71(8) . . ?
C5 C4 S1 119.42(8) . . ?
C10 C5 C6 120.73(10) . . ?
C10 C5 C4 120.46(10) . . ?
C6 C5 C4 118.66(10) . . ?
C7 C6 C5 118.43(11) . . ?
C7 C6 C17 119.38(10) . . ?
C5 C6 C17 122.18(10) . . ?
C6 C7 C8 122.07(11) . . ?
C9 C8 C7 118.23(11) . . ?
C9 C8 C14 120.95(10) . . ?
C7 C8 C14 120.81(10) . . ?
C8 C9 C10 122.05(11) . . ?
C9 C10 C5 118.40(10) . . ?
C9 C10 C11 119.01(10) . . ?
C5 C10 C11 122.60(10) . . ?
C10 C11 C12 111.26(10) . . ?
C10 C11 C13 111.10(10) . . ?
C12 C11 C13 110.47(11) . . ?
C8 C14 C16 111.22(10) . . ?
C8 C14 C15 110.87(10) . . ?
C16 C14 C15 111.30(10) . . ?
C6 C17 C18 112.01(10) . . ?
C6 C17 C19 110.47(11) . . ?
C18 C17 C19 110.78(11) . . ?
C21 C20 C25 119.36(10) . . ?
C21 C20 C3 116.27(10) . . ?
C25 C20 C3 124.23(10) . . ?
C22 C21 C20 120.08(11) . . ?
F1 C22 C21 120.33(11) . . ?
F1 C22 C23 119.17(10) . . ?
C21 C22 C23 120.48(11) . . ?
F2 C23 C24 120.38(11) . . ?
F2 C23 C22 119.02(10) . . ?
C24 C23 C22 120.58(11) . . ?
C23 C24 C25 120.14(11) . . ?
C24 C25 C20 119.15(10) . . ?
C24 C25 C28 117.08(10) . . ?
C20 C25 C28 123.71(10) . . ?
C28 C27 C26 130.17(10) . . ?
C28 C27 S2 108.63(8) . . ?
C26 C27 S2 121.19(9) . . ?
C27 C28 N2 116.05(10) . . ?
C27 C28 C25 125.80(10) . . ?
N2 C28 C25 118.02(10) . . ?
N2 C29 C30 124.68(10) . . ?
N2 C29 S2 113.86(8) . . ?
C30 C29 S2 121.44(8) . . ?
C35 C30 C31 120.84(10) . . ?
C35 C30 C29 119.59(10) . . ?
C31 C30 C29 119.56(10) . . ?
C32 C31 C30 118.17(11) . . ?
C32 C31 C42 120.11(10) . . ?
C30 C31 C42 121.71(10) . . ?
C33 C32 C31 122.30(11) . . ?
C32 C33 C34 118.19(11) . . ?
C32 C33 C39 120.78(11) . . ?
C34 C33 C39 121.03(11) . . ?
C33 C34 C35 121.95(11) . . ?
C34 C35 C30 118.51(10) . . ?
C34 C35 C36 118.88(10) . . ?
C30 C35 C36 122.59(10) . . ?
C35 C36 C38 110.95(10) . . ?
C35 C36 C37 111.30(10) . . ?
C38 C36 C37 112.01(11) . . ?
C33 C39 C41 111.56(11) . . ?
C33 C39 C40 111.45(10) . . ?
C41 C39 C40 110.30(11) . . ?
C31 C42 C44 112.70(10) . . ?
C31 C42 C43 110.23(10) . . ?
C44 C42 C43 110.91(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 S1 C2 C3 0.19(9) . . . . ?
C4 S1 C2 C1 178.96(10) . . . . ?
C1 C2 C3 N1 -178.38(11) . . . . ?
S1 C2 C3 N1 0.22(13) . . . . ?
C1 C2 C3 C20 -5.3(2) . . . . ?
S1 C2 C3 C20 173.32(9) . . . . ?
C4 N1 C3 C2 -0.67(14) . . . . ?
C4 N1 C3 C20 -174.36(10) . . . . ?
C3 N1 C4 C5 176.18(11) . . . . ?
C3 N1 C4 S1 0.80(12) . . . . ?
C2 S1 C4 N1 -0.59(9) . . . . ?
C2 S1 C4 C5 -176.34(10) . . . . ?
N1 C4 C5 C10 113.30(14) . . . . ?
S1 C4 C5 C10 -71.55(13) . . . . ?
N1 C4 C5 C6 -71.18(16) . . . . ?
S1 C4 C5 C6 103.97(11) . . . . ?
C10 C5 C6 C7 1.34(17) . . . . ?
C4 C5 C6 C7 -174.16(11) . . . . ?
C10 C5 C6 C17 -179.67(11) . . . . ?
C4 C5 C6 C17 4.83(17) . . . . ?
C5 C6 C7 C8 1.54(18) . . . . ?
C17 C6 C7 C8 -177.48(11) . . . . ?
C6 C7 C8 C9 -3.31(18) . . . . ?
C6 C7 C8 C14 175.39(11) . . . . ?
C7 C8 C9 C10 2.28(17) . . . . ?
C14 C8 C9 C10 -176.42(11) . . . . ?
C8 C9 C10 C5 0.46(17) . . . . ?
C8 C9 C10 C11 -179.47(11) . . . . ?
C6 C5 C10 C9 -2.30(17) . . . . ?
C4 C5 C10 C9 173.12(10) . . . . ?
C6 C5 C10 C11 177.63(11) . . . . ?
C4 C5 C10 C11 -6.96(17) . . . . ?
C9 C10 C11 C12 -68.42(14) . . . . ?
C5 C10 C11 C12 111.66(12) . . . . ?
C9 C10 C11 C13 55.11(15) . . . . ?
C5 C10 C11 C13 -124.81(13) . . . . ?
C9 C8 C14 C16 -115.24(12) . . . . ?
C7 C8 C14 C16 66.08(15) . . . . ?
C9 C8 C14 C15 120.35(12) . . . . ?
C7 C8 C14 C15 -58.33(15) . . . . ?
C7 C6 C17 C18 52.32(15) . . . . ?
C5 C6 C17 C18 -126.66(13) . . . . ?
C7 C6 C17 C19 -71.69(15) . . . . ?
C5 C6 C17 C19 109.33(14) . . . . ?
C2 C3 C20 C21 -127.65(12) . . . . ?
N1 C3 C20 C21 45.34(14) . . . . ?
C2 C3 C20 C25 47.96(17) . . . . ?
N1 C3 C20 C25 -139.05(11) . . . . ?
C25 C20 C21 C22 -2.92(17) . . . . ?
C3 C20 C21 C22 172.91(10) . . . . ?
C20 C21 C22 F1 -179.40(10) . . . . ?
C20 C21 C22 C23 -1.25(17) . . . . ?
F1 C22 C23 F2 -0.13(17) . . . . ?
C21 C22 C23 F2 -178.30(10) . . . . ?
F1 C22 C23 C24 -178.83(11) . . . . ?
C21 C22 C23 C24 3.00(18) . . . . ?
F2 C23 C24 C25 -179.18(10) . . . . ?
C22 C23 C24 C25 -0.50(18) . . . . ?
C23 C24 C25 C20 -3.65(17) . . . . ?
C23 C24 C25 C28 173.61(11) . . . . ?
C21 C20 C25 C24 5.33(17) . . . . ?
C3 C20 C25 C24 -170.15(11) . . . . ?
C21 C20 C25 C28 -171.75(11) . . . . ?
C3 C20 C25 C28 12.77(18) . . . . ?
C29 S2 C27 C28 0.54(9) . . . . ?
C29 S2 C27 C26 -179.99(10) . . . . ?
C26 C27 C28 N2 -179.32(11) . . . . ?
S2 C27 C28 N2 0.10(13) . . . . ?
C26 C27 C28 C25 -3.7(2) . . . . ?
S2 C27 C28 C25 175.73(9) . . . . ?
C29 N2 C28 C27 -0.94(14) . . . . ?
C29 N2 C28 C25 -176.92(10) . . . . ?
C24 C25 C28 C27 -129.95(12) . . . . ?
C20 C25 C28 C27 47.18(17) . . . . ?
C24 C25 C28 N2 45.60(15) . . . . ?
C20 C25 C28 N2 -137.27(11) . . . . ?
C28 N2 C29 C30 -177.06(10) . . . . ?
C28 N2 C29 S2 1.34(12) . . . . ?
C27 S2 C29 N2 -1.12(9) . . . . ?
C27 S2 C29 C30 177.35(10) . . . . ?
N2 C29 C30 C35 104.24(14) . . . . ?
S2 C29 C30 C35 -74.06(13) . . . . ?
N2 C29 C30 C31 -74.60(15) . . . . ?
S2 C29 C30 C31 107.11(11) . . . . ?
C35 C30 C31 C32 -1.96(17) . . . . ?
C29 C30 C31 C32 176.86(10) . . . . ?
C35 C30 C31 C42 179.52(10) . . . . ?
C29 C30 C31 C42 -1.66(17) . . . . ?
C30 C31 C32 C33 0.42(18) . . . . ?
C42 C31 C32 C33 178.96(11) . . . . ?
C31 C32 C33 C34 1.31(18) . . . . ?
C31 C32 C33 C39 -178.32(11) . . . . ?
C32 C33 C34 C35 -1.58(18) . . . . ?
C39 C33 C34 C35 178.06(11) . . . . ?
C33 C34 C35 C30 0.09(18) . . . . ?
C33 C34 C35 C36 -178.29(11) . . . . ?
C31 C30 C35 C34 1.72(17) . . . . ?
C29 C30 C35 C34 -177.10(10) . . . . ?
C31 C30 C35 C36 -179.96(10) . . . . ?
C29 C30 C35 C36 1.22(16) . . . . ?
C34 C35 C36 C38 68.73(14) . . . . ?
C30 C35 C36 C38 -109.59(13) . . . . ?
C34 C35 C36 C37 -56.72(14) . . . . ?
C30 C35 C36 C37 124.96(12) . . . . ?
C32 C33 C39 C41 119.91(13) . . . . ?
C34 C33 C39 C41 -59.72(16) . . . . ?
C32 C33 C39 C40 -116.30(13) . . . . ?
C34 C33 C39 C40 64.07(16) . . . . ?
C32 C31 C42 C44 43.06(15) . . . . ?
C30 C31 C42 C44 -138.45(12) . . . . ?
C32 C31 C42 C43 -81.44(14) . . . . ?
C30 C31 C42 C43 97.05(13) . . . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.042


_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_chemical_absolute_configuration ?
