# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_hl-der-m_auto
_database_code_depnum_ccdc_archive 'CCDC 2260119'
loop_
_audit_author_name
_audit_author_address
'Lei Huang'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2023-02-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H24 O5 S'
_chemical_formula_sum            'C29 H24 O5 S'
_chemical_formula_weight         484.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O1S1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2396(3)
_cell_length_b                   7.38829(13)
_cell_length_c                   27.2180(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.5426(19)
_cell_angle_gamma                90
_cell_volume                     2458.90(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3866
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7370
_cell_measurement_theta_min      5.9580
_shelx_estimated_absorpt_T_max   0.746
_shelx_estimated_absorpt_T_min   0.708
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8851
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.842
_diffrn_reflns_theta_min         3.898
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -61.00   1.00    4.00    --  -41.76 125.00 150.00   26
  2  ω    -65.00  33.00   1.00    4.00    --  -41.76  38.00 -90.00   98
  3  ω    -66.00  26.00   1.00    4.00    --  -41.76  38.00-180.00   92
  4  ω    130.00 162.00   1.00   10.00    --  106.05 125.00 -30.00   32
  5  ω     79.00 176.00   1.00   10.00    --  106.05  30.00 150.00   97
  6  ω     38.00  99.00   1.00   10.00    --  106.05-125.00 -60.00   61
  7  ω     66.00 112.00   1.00   10.00    --  106.05-125.00-150.00   46
  8  ω     87.00 159.00   1.00   10.00    --  106.05  30.00-120.00   72
  9  ω    111.00 148.00   1.00   10.00    --  106.05  77.00-120.00   37
 10  ω     61.00 116.00   1.00   10.00    --  106.05-130.00 170.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0593750000
_diffrn_orient_matrix_UB_12      -0.0212011000
_diffrn_orient_matrix_UB_13      0.0507775000
_diffrn_orient_matrix_UB_21      -0.1044599000
_diffrn_orient_matrix_UB_22      0.0600000000
_diffrn_orient_matrix_UB_23      0.0250506000
_diffrn_orient_matrix_UB_31      -0.0379238000
_diffrn_orient_matrix_UB_32      -0.1985405000
_diffrn_orient_matrix_UB_33      0.0021232000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3821
_reflns_number_total             4740
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00051(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.3061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1250
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C15(H15)
1.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
1.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C11(H11), C9(H9), C27(H27), C21(H21), C17(H17), C5(H5),
 C24(H24), C3(H3), C26(H26), C25(H25), C20(H20), C19(H19), C18(H18), C1(H1),
 C2(H2), C6(H6)
1.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.75312(4) 0.55285(6) 0.36001(2) 0.04969(15) Uani 1 1 d . . . . .
O2 O 0.86794(12) 0.5548(2) 0.35145(5) 0.0626(4) Uani 1 1 d . . . . .
O1 O 0.79967(13) 0.76726(17) 0.50663(5) 0.0620(4) Uani 1 1 d . . . . .
O3 O 0.69256(15) 0.3919(2) 0.34839(6) 0.0710(4) Uani 1 1 d . . . . .
O5 O 0.93188(18) 0.9293(3) 0.29938(6) 0.0915(6) Uani 1 1 d . . . . .
O4 O 0.88256(18) 0.9554(3) 0.37727(6) 0.0877(6) Uani 1 1 d . . . . .
C13 C 0.79429(14) 0.5007(2) 0.46093(6) 0.0410(4) Uani 1 1 d . . . . .
C8 C 0.88996(14) 0.5337(2) 0.54824(7) 0.0440(4) Uani 1 1 d . . . . .
C12 C 0.80731(16) 0.3210(2) 0.45290(7) 0.0483(4) Uani 1 1 d . . . . .
H12 H 0.7771 0.2799 0.4230 0.058 Uiso 1 1 calc R U . . .
C15 C 0.73511(14) 0.6222(2) 0.42296(6) 0.0433(4) Uani 1 1 d . . . . .
H15 H 0.7702 0.7411 0.4263 0.052 Uiso 1 1 calc R U . . .
C14 C 0.82664(14) 0.6063(2) 0.50527(6) 0.0429(4) Uani 1 1 d . . . . .
C7 C 0.91335(16) 0.6686(3) 0.58891(7) 0.0515(4) Uani 1 1 d . . . . .
H7A H 0.9259 0.7867 0.5746 0.062 Uiso 1 1 calc R U . . .
H7B H 0.9796 0.6332 0.6073 0.062 Uiso 1 1 calc R U . . .
C16 C 0.61511(16) 0.6540(3) 0.43172(7) 0.0523(4) Uani 1 1 d . . . . .
C10 C 0.91324(17) 0.2037(3) 0.52623(8) 0.0551(5) Uani 1 1 d . . . . .
H10 H 0.9451 0.0989 0.5393 0.066 Uiso 1 1 calc R U . . .
C4 C 0.82017(17) 0.6819(3) 0.62370(7) 0.0547(5) Uani 1 1 d . . . . .
C11 C 0.85919(17) 0.1851(2) 0.48237(8) 0.0540(5) Uani 1 1 d . . . . .
H11 H 0.8554 0.0682 0.4698 0.065 Uiso 1 1 calc R U . . .
C9 C 0.92795(16) 0.3619(3) 0.55512(7) 0.0507(4) Uani 1 1 d . . . . .
H9 H 0.9711 0.3457 0.5838 0.061 Uiso 1 1 calc R U . . .
C22 C 0.68993(18) 0.7316(3) 0.32558(7) 0.0539(5) Uani 1 1 d . . . . .
C23 C 0.7473(2) 0.8875(3) 0.31452(7) 0.0618(5) Uani 1 1 d . . . . .
C28 C 0.8597(2) 0.9259(3) 0.33495(8) 0.0712(7) Uani 1 1 d . . . . .
C27 C 0.5831(2) 0.7066(4) 0.30816(9) 0.0729(6) Uani 1 1 d . . . . .
H27 H 0.5453 0.6017 0.3158 0.088 Uiso 1 1 calc R U . . .
C21 C 0.54181(19) 0.5120(4) 0.43271(10) 0.0717(6) Uani 1 1 d . . . . .
H21 H 0.5664 0.3937 0.4293 0.086 Uiso 1 1 calc R U . . .
C17 C 0.5784(2) 0.8293(4) 0.43778(9) 0.0695(6) Uani 1 1 d . . . . .
H17 H 0.6270 0.9259 0.4371 0.083 Uiso 1 1 calc R U . . .
C5 C 0.7429(2) 0.8179(4) 0.61952(10) 0.0770(7) Uani 1 1 d . . . . .
H5 H 0.7475 0.9039 0.5947 0.092 Uiso 1 1 calc R U . . .
C24 C 0.6950(3) 1.0172(4) 0.28472(9) 0.0873(9) Uani 1 1 d . . . . .
H24 H 0.7323 1.1218 0.2764 0.105 Uiso 1 1 calc R U . . .
C3 C 0.8121(3) 0.5596(4) 0.66115(10) 0.0845(8) Uani 1 1 d . . . . .
H3 H 0.8642 0.4685 0.6652 0.101 Uiso 1 1 calc R U . . .
C26 C 0.5331(3) 0.8394(5) 0.27928(10) 0.0977(10) Uani 1 1 d . . . . .
H26 H 0.4610 0.8247 0.2678 0.117 Uiso 1 1 calc R U . . .
C25 C 0.5892(3) 0.9925(5) 0.26749(11) 0.1046(12) Uani 1 1 d . . . . .
H25 H 0.5553 1.0802 0.2477 0.126 Uiso 1 1 calc R U . . .
C20 C 0.4318(2) 0.5450(6) 0.43868(12) 0.0972(10) Uani 1 1 d . . . . .
H20 H 0.3824 0.4493 0.4386 0.117 Uiso 1 1 calc R U . . .
C19 C 0.3958(2) 0.7189(6) 0.44464(12) 0.1042(12) Uani 1 1 d . . . . .
H19 H 0.3219 0.7410 0.4486 0.125 Uiso 1 1 calc R U . . .
C18 C 0.4679(2) 0.8599(5) 0.44488(11) 0.0944(10) Uani 1 1 d . . . . .
H18 H 0.4430 0.9772 0.4498 0.113 Uiso 1 1 calc R U . . .
C1 C 0.6508(3) 0.7027(6) 0.68803(14) 0.1171(12) Uani 1 1 d . . . . .
H1 H 0.5933 0.7080 0.7092 0.140 Uiso 1 1 calc R U . . .
C2 C 0.7271(3) 0.5699(5) 0.69324(13) 0.1169(13) Uani 1 1 d . . . . .
H2 H 0.7224 0.4855 0.7184 0.140 Uiso 1 1 calc R U . . .
C6 C 0.6590(3) 0.8277(5) 0.65175(13) 0.1060(11) Uani 1 1 d . . . . .
H6 H 0.6079 0.9205 0.6486 0.127 Uiso 1 1 calc R U . . .
C29 C 1.0415(3) 0.9737(6) 0.31495(14) 0.1316(16) Uani 1 1 d . . . . .
H29A H 1.0889 0.9548 0.2882 0.197 Uiso 1 1 calc R U . . .
H29B H 1.0644 0.8979 0.3421 0.197 Uiso 1 1 calc R U . . .
H29C H 1.0450 1.0983 0.3249 0.197 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
S1 O2 1.4348(16) . ?
S1 O3 1.4292(15) . ?
S1 C15 1.8112(18) . ?
S1 C22 1.776(2) . ?
O1 C14 1.235(2) . ?
O5 C28 1.339(3) . ?
O5 C29 1.427(4) . ?
O4 C28 1.193(3) . ?
C13 C12 1.356(2) . ?
C13 C15 1.527(2) . ?
C13 C14 1.477(2) . ?
C8 C14 1.475(2) . ?
C8 C7 1.508(3) . ?
C8 C9 1.361(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.417(3) . ?
C15 H15 0.9800 . ?
C15 C16 1.517(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C4 1.517(3) . ?
C16 C21 1.381(3) . ?
C16 C17 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.346(3) . ?
C10 C9 1.416(3) . ?
C4 C5 1.381(3) . ?
C4 C3 1.369(3) . ?
C11 H11 0.9300 . ?
C9 H9 0.9300 . ?
C22 C23 1.389(3) . ?
C22 C27 1.384(3) . ?
C23 C28 1.488(4) . ?
C23 C24 1.393(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.383(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.385(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.393(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.369(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.390(4) . ?
C26 H26 0.9300 . ?
C26 C25 1.368(5) . ?
C25 H25 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.371(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.365(5) . ?
C18 H18 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.357(5) . ?
C1 C6 1.359(5) . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

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
O2 S1 C15 108.18(9) . . ?
O2 S1 C22 108.26(10) . . ?
O3 S1 O2 118.33(10) . . ?
O3 S1 C15 111.18(9) . . ?
O3 S1 C22 106.99(10) . . ?
C22 S1 C15 102.72(8) . . ?
C28 O5 C29 115.5(2) . . ?
C12 C13 C15 121.48(17) . . ?
C12 C13 C14 128.32(17) . . ?
C14 C13 C15 110.13(14) . . ?
C14 C8 C7 114.66(15) . . ?
C9 C8 C14 127.77(17) . . ?
C9 C8 C7 117.57(17) . . ?
C13 C12 H12 114.5 . . ?
C13 C12 C11 130.92(19) . . ?
C11 C12 H12 114.5 . . ?
S1 C15 H15 105.7 . . ?
C13 C15 S1 113.56(12) . . ?
C13 C15 H15 105.7 . . ?
C16 C15 S1 110.60(12) . . ?
C16 C15 C13 114.71(15) . . ?
C16 C15 H15 105.7 . . ?
O1 C14 C13 118.10(16) . . ?
O1 C14 C8 117.29(16) . . ?
C8 C14 C13 124.61(15) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C8 C7 C4 112.17(16) . . ?
H7A C7 H7B 107.9 . . ?
C4 C7 H7A 109.2 . . ?
C4 C7 H7B 109.2 . . ?
C21 C16 C15 121.34(19) . . ?
C21 C16 C17 119.6(2) . . ?
C17 C16 C15 119.04(19) . . ?
C11 C10 H10 115.8 . . ?
C11 C10 C9 128.48(17) . . ?
C9 C10 H10 115.8 . . ?
C5 C4 C7 121.8(2) . . ?
C3 C4 C7 120.2(2) . . ?
C3 C4 C5 118.0(2) . . ?
C12 C11 H11 115.8 . . ?
C10 C11 C12 128.32(18) . . ?
C10 C11 H11 115.8 . . ?
C8 C9 C10 131.21(18) . . ?
C8 C9 H9 114.4 . . ?
C10 C9 H9 114.4 . . ?
C23 C22 S1 121.20(17) . . ?
C27 C22 S1 117.66(17) . . ?
C27 C22 C23 121.1(2) . . ?
C22 C23 C28 123.06(19) . . ?
C22 C23 C24 118.2(3) . . ?
C24 C23 C28 118.7(2) . . ?
O5 C28 C23 111.2(2) . . ?
O4 C28 O5 124.1(3) . . ?
O4 C28 C23 124.7(2) . . ?
C22 C27 H27 120.4 . . ?
C26 C27 C22 119.2(3) . . ?
C26 C27 H27 120.4 . . ?
C16 C21 H21 119.9 . . ?
C16 C21 C20 120.3(3) . . ?
C20 C21 H21 119.9 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 H24 119.6 . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C27 C26 H26 119.8 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H25 119.8 . . ?
C21 C20 H20 120.1 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.1 . . ?
C20 C19 H19 119.8 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C2 C1 H1 120.2 . . ?
C2 C1 C6 119.6(3) . . ?
C6 C1 H1 120.2 . . ?
C3 C2 H2 119.8 . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2 119.8 . . ?
C5 C6 H6 119.8 . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 H6 119.8 . . ?
O5 C29 H29A 109.5 . . ?
O5 C29 H29B 109.5 . . ?
O5 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

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
S1 C15 C16 C21 70.0(2) . . . . ?
S1 C15 C16 C17 -108.58(19) . . . . ?
S1 C22 C23 C28 -7.1(3) . . . . ?
S1 C22 C23 C24 175.94(17) . . . . ?
S1 C22 C27 C26 -177.0(2) . . . . ?
O2 S1 C15 C13 -59.09(14) . . . . ?
O2 S1 C15 C16 170.29(13) . . . . ?
O2 S1 C22 C23 -28.39(19) . . . . ?
O2 S1 C22 C27 148.60(17) . . . . ?
O3 S1 C15 C13 72.43(15) . . . . ?
O3 S1 C15 C16 -58.19(15) . . . . ?
O3 S1 C22 C23 -156.96(16) . . . . ?
O3 S1 C22 C27 20.0(2) . . . . ?
C13 C12 C11 C10 -2.6(4) . . . . ?
C13 C15 C16 C21 -60.0(2) . . . . ?
C13 C15 C16 C17 121.4(2) . . . . ?
C8 C7 C4 C5 -98.4(2) . . . . ?
C8 C7 C4 C3 83.0(3) . . . . ?
C12 C13 C15 S1 -32.6(2) . . . . ?
C12 C13 C15 C16 95.9(2) . . . . ?
C12 C13 C14 O1 -174.46(19) . . . . ?
C12 C13 C14 C8 6.0(3) . . . . ?
C15 S1 C22 C23 85.89(17) . . . . ?
C15 S1 C22 C27 -97.11(18) . . . . ?
C15 C13 C12 C11 179.53(19) . . . . ?
C15 C13 C14 O1 2.6(2) . . . . ?
C15 C13 C14 C8 -176.92(16) . . . . ?
C15 C16 C21 C20 -177.2(2) . . . . ?
C15 C16 C17 C18 178.7(2) . . . . ?
C14 C13 C12 C11 -3.7(3) . . . . ?
C14 C13 C15 S1 150.06(12) . . . . ?
C14 C13 C15 C16 -81.40(18) . . . . ?
C14 C8 C7 C4 85.3(2) . . . . ?
C14 C8 C9 C10 -4.7(3) . . . . ?
C7 C8 C14 O1 0.2(2) . . . . ?
C7 C8 C14 C13 179.71(16) . . . . ?
C7 C8 C9 C10 174.82(19) . . . . ?
C7 C4 C5 C6 -179.7(3) . . . . ?
C7 C4 C3 C2 -179.9(3) . . . . ?
C16 C21 C20 C19 -1.3(5) . . . . ?
C16 C17 C18 C19 -1.6(4) . . . . ?
C4 C5 C6 C1 -0.4(5) . . . . ?
C4 C3 C2 C1 -0.4(6) . . . . ?
C11 C10 C9 C8 2.7(4) . . . . ?
C9 C8 C14 O1 179.67(19) . . . . ?
C9 C8 C14 C13 -0.8(3) . . . . ?
C9 C8 C7 C4 -94.3(2) . . . . ?
C9 C10 C11 C12 3.1(4) . . . . ?
C22 S1 C15 C13 -173.44(13) . . . . ?
C22 S1 C15 C16 55.94(15) . . . . ?
C22 C23 C28 O5 115.0(2) . . . . ?
C22 C23 C28 O4 -67.0(3) . . . . ?
C22 C23 C24 C25 1.0(4) . . . . ?
C22 C27 C26 C25 0.9(4) . . . . ?
C23 C22 C27 C26 0.0(3) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C28 C23 C24 C25 -176.1(2) . . . . ?
C27 C22 C23 C28 176.0(2) . . . . ?
C27 C22 C23 C24 -1.0(3) . . . . ?
C27 C26 C25 C24 -0.9(5) . . . . ?
C21 C16 C17 C18 0.1(3) . . . . ?
C21 C20 C19 C18 -0.2(5) . . . . ?
C17 C16 C21 C20 1.4(4) . . . . ?
C5 C4 C3 C2 1.5(5) . . . . ?
C24 C23 C28 O5 -68.0(3) . . . . ?
C24 C23 C28 O4 109.9(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C20 C19 C18 C17 1.7(5) . . . . ?
C2 C1 C6 C5 1.5(7) . . . . ?
C6 C1 C2 C3 -1.2(7) . . . . ?
C29 O5 C28 O4 -0.8(4) . . . . ?
C29 O5 C28 C23 177.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.752
####################################################################### 
# 
# 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_hl-1_autored
_database_code_depnum_ccdc_archive 'CCDC 2260124'
loop_
_audit_author_name
_audit_author_address
'Lei Huang'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C F3 O3 S, C24 H26 N O'
_chemical_formula_sum            'C25 H26 F3 N O4 S'
_chemical_formula_weight         493.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20h20o2s1f3
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2016(2)
_cell_length_b                   16.5260(2)
_cell_length_c                   11.22516(19)
_cell_angle_alpha                90
_cell_angle_beta                 103.2304(16)
_cell_angle_gamma                90
_cell_volume                     2745.15(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8960
_cell_measurement_theta_min      3.9880
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.737
_exptl_absorpt_coefficient_mu    1.474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10398
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.989
_diffrn_reflns_theta_min         4.010
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -22.00   1.00    3.00    --  -41.76 -57.00-150.00   93
  2  ω    -62.00  31.00   1.00    3.00    --  -41.76  38.00-180.00   93
  3  ω     39.00  71.00   1.00    3.00    --   41.76 -99.00-180.00   32
  4  ω    152.00 178.00   1.00    6.00    --  106.05  77.00   0.00   26
  5  ω     42.00 112.00   1.00    6.00    --  106.05-125.00 120.00   70
  6  ω     87.00 175.00   1.00    6.00    --  106.05  30.00  30.00   88
  7  ω     59.00  85.00   1.00    6.00    --  106.05-125.00-180.00   26
  8  ω     32.00 133.00   1.00    6.00    --  106.05 -30.00-150.00  101
  9  ω     41.00 138.00   1.00    6.00    --  106.05 -77.00  90.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0772890000
_diffrn_orient_matrix_UB_12      0.0020908000
_diffrn_orient_matrix_UB_13      -0.1158262000
_diffrn_orient_matrix_UB_21      -0.0689590000
_diffrn_orient_matrix_UB_22      0.0114991000
_diffrn_orient_matrix_UB_23      0.0800447000
_diffrn_orient_matrix_UB_31      0.0103061000
_diffrn_orient_matrix_UB_32      0.0924904000
_diffrn_orient_matrix_UB_33      -0.0073906000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4538
_reflns_number_total             5335
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0793P)²+0.6118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1555
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C6(H6)
1.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C15(H15), C8(H8), C14(H14), C11(H11), C17(H17), C12(H12),
 C13(H13), C21(H21), C18(H18), C19(H19), C20(H20), C10(H10)
1.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.08284(3) 0.33580(3) 0.28979(5) 0.05965(18) Uani 1 1 d . . . . .
O1 O 0.39310(9) 0.53213(8) 0.48291(14) 0.0644(4) Uani 1 1 d . . . . .
N1 N 0.14402(10) 0.56930(9) 0.33045(14) 0.0504(4) Uani 1 1 d . . . . .
O4 O -0.02489(12) 0.39163(11) 0.36572(17) 0.0857(5) Uani 1 1 d . . . . .
C6 C 0.17084(11) 0.48255(10) 0.37850(16) 0.0462(4) Uani 1 1 d . . . . .
H6 H 0.1288 0.4445 0.3279 0.055 Uiso 1 1 calc R U . . .
C2 C 0.35360(12) 0.41232(11) 0.57717(17) 0.0493(4) Uani 1 1 d . . . . .
O2 O -0.03824(15) 0.27486(11) 0.2367(2) 0.1006(6) Uani 1 1 d . . . . .
C7 C 0.26547(12) 0.46076(10) 0.36776(16) 0.0471(4) Uani 1 1 d . . . . .
C5 C 0.16337(12) 0.47188(11) 0.51061(17) 0.0516(4) Uani 1 1 d . . . . .
H5A H 0.2027 0.5102 0.5628 0.062 Uiso 1 1 calc R U . . .
H5B H 0.1018 0.4821 0.5170 0.062 Uiso 1 1 calc R U . . .
C3 C 0.27539(13) 0.36133(11) 0.58160(19) 0.0560(4) Uani 1 1 d . . . . .
H3 H 0.2860 0.3080 0.6073 0.067 Uiso 1 1 calc R U . . .
C1 C 0.34166(12) 0.47526(10) 0.47912(17) 0.0490(4) Uani 1 1 d . . . . .
F1 F -0.07263(19) 0.43107(14) 0.1090(2) 0.1399(8) Uani 1 1 d . . . . .
C4 C 0.19018(13) 0.38694(12) 0.55102(19) 0.0573(5) Uani 1 1 d . . . . .
H4 H 0.1446 0.3502 0.5549 0.069 Uiso 1 1 calc R U . . .
C15 C 0.43862(13) 0.40221(12) 0.64383(17) 0.0543(4) Uani 1 1 d . . . . .
H15 H 0.4806 0.4385 0.6261 0.065 Uiso 1 1 calc R U . . .
O3 O -0.15579(15) 0.30742(16) 0.3367(2) 0.1147(8) Uani 1 1 d . . . . .
C8 C 0.28884(13) 0.42244(12) 0.27431(18) 0.0565(4) Uani 1 1 d . . . . .
H8 H 0.3507 0.4150 0.2835 0.068 Uiso 1 1 calc R U . . .
F2 F -0.19022(18) 0.35594(19) 0.07601(19) 0.1595(10) Uani 1 1 d . . . . .
C9 C 0.23288(14) 0.39026(12) 0.15983(19) 0.0585(5) Uani 1 1 d . . . . .
C23 C 0.04989(13) 0.58755(13) 0.3443(2) 0.0655(5) Uani 1 1 d . . . . .
H23A H 0.0101 0.5444 0.3090 0.098 Uiso 1 1 calc R U . . .
H23B H 0.0294 0.6373 0.3031 0.098 Uiso 1 1 calc R U . . .
H23C H 0.0501 0.5925 0.4295 0.098 Uiso 1 1 calc R U . . .
F3 F -0.1814(2) 0.45653(16) 0.1958(2) 0.1619(11) Uani 1 1 d . . . . .
C22 C 0.20656(14) 0.63306(11) 0.3977(2) 0.0648(5) Uani 1 1 d . . . . .
H22A H 0.2046 0.6326 0.4826 0.097 Uiso 1 1 calc R U . . .
H22B H 0.1879 0.6852 0.3633 0.097 Uiso 1 1 calc R U . . .
H22C H 0.2671 0.6222 0.3901 0.097 Uiso 1 1 calc R U . . .
C16 C 0.47533(14) 0.34372(13) 0.73915(18) 0.0597(5) Uani 1 1 d . . . . .
C24 C 0.14394(19) 0.57443(15) 0.1974(2) 0.0749(6) Uani 1 1 d . . . . .
H24A H 0.2040 0.5652 0.1866 0.112 Uiso 1 1 calc R U . . .
H24B H 0.1239 0.6272 0.1670 0.112 Uiso 1 1 calc R U . . .
H24C H 0.1039 0.5342 0.1531 0.112 Uiso 1 1 calc R U . . .
C14 C 0.26235(19) 0.40074(17) 0.0522(2) 0.0784(7) Uani 1 1 d . . . . .
H14 H 0.3161 0.4280 0.0538 0.094 Uiso 1 1 calc R U . . .
C11 C 0.10385(19) 0.31752(16) 0.0441(3) 0.0840(7) Uani 1 1 d . . . . .
H11 H 0.0503 0.2897 0.0416 0.101 Uiso 1 1 calc R U . . .
C17 C 0.42506(18) 0.30407(17) 0.8106(2) 0.0782(7) Uani 1 1 d . . . . .
H17 H 0.3636 0.3148 0.7991 0.094 Uiso 1 1 calc R U . . .
C12 C 0.1327(2) 0.32878(18) -0.0610(3) 0.0902(8) Uani 1 1 d . . . . .
H12 H 0.0993 0.3084 -0.1348 0.108 Uiso 1 1 calc R U . . .
C13 C 0.2115(2) 0.3705(2) -0.0573(2) 0.0950(9) Uani 1 1 d . . . . .
H13 H 0.2309 0.3786 -0.1291 0.114 Uiso 1 1 calc R U . . .
C21 C 0.56786(17) 0.32817(19) 0.7618(2) 0.0864(8) Uani 1 1 d . . . . .
H21 H 0.6033 0.3562 0.7182 0.104 Uiso 1 1 calc R U . . .
C25 C -0.1350(2) 0.3971(2) 0.1599(3) 0.0937(8) Uani 1 1 d . . . . .
C18 C 0.4657(3) 0.2489(2) 0.8985(3) 0.1056(10) Uani 1 1 d . . . . .
H18 H 0.4317 0.2230 0.9463 0.127 Uiso 1 1 calc R U . . .
C19 C 0.5566(3) 0.2322(2) 0.9154(3) 0.1185(12) Uani 1 1 d . . . . .
H19 H 0.5833 0.1937 0.9729 0.142 Uiso 1 1 calc R U . . .
C20 C 0.6076(2) 0.2716(2) 0.8484(3) 0.1160(12) Uani 1 1 d . . . . .
H20 H 0.6690 0.2604 0.8609 0.139 Uiso 1 1 calc R U . . .
C10 C 0.15339(17) 0.34707(13) 0.1545(2) 0.0720(6) Uani 1 1 d . . . . .
H10 H 0.1334 0.3380 0.2257 0.086 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
S1 O4 1.4179(16) . ?
S1 O2 1.4188(19) . ?
S1 O3 1.4124(19) . ?
S1 C25 1.804(3) . ?
O1 C1 1.217(2) . ?
N1 C6 1.553(2) . ?
N1 C23 1.505(2) . ?
N1 C22 1.502(2) . ?
N1 C24 1.496(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.514(2) . ?
C6 C5 1.523(3) . ?
C2 C3 1.467(3) . ?
C2 C1 1.495(2) . ?
C2 C15 1.347(3) . ?
C7 C1 1.516(3) . ?
C7 C8 1.341(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.503(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.331(3) . ?
F1 C25 1.337(4) . ?
C4 H4 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.455(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.469(3) . ?
F2 C25 1.301(4) . ?
C9 C14 1.392(3) . ?
C9 C10 1.393(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
F3 C25 1.323(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C16 C17 1.392(3) . ?
C16 C21 1.395(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C13 1.387(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.362(4) . ?
C11 C10 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(4) . ?
C13 H13 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.384(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.362(5) . ?
C20 H20 0.9300 . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O2 115.05(13) . . ?
O4 S1 C25 102.59(13) . . ?
O2 S1 C25 102.93(14) . . ?
O3 S1 O4 115.13(13) . . ?
O3 S1 O2 114.35(15) . . ?
O3 S1 C25 104.51(16) . . ?
C23 N1 C6 109.24(14) . . ?
C22 N1 C6 112.80(13) . . ?
C22 N1 C23 108.38(16) . . ?
C24 N1 C6 109.83(14) . . ?
C24 N1 C23 107.94(17) . . ?
C24 N1 C22 108.53(17) . . ?
N1 C6 H6 107.8 . . ?
C7 C6 N1 111.75(13) . . ?
C7 C6 H6 107.8 . . ?
C7 C6 C5 109.50(14) . . ?
C5 C6 N1 111.89(14) . . ?
C5 C6 H6 107.8 . . ?
C3 C2 C1 117.50(16) . . ?
C15 C2 C3 126.26(17) . . ?
C15 C2 C1 115.76(16) . . ?
C6 C7 C1 117.21(15) . . ?
C8 C7 C6 126.95(17) . . ?
C8 C7 C1 115.49(16) . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C4 C5 C6 109.06(16) . . ?
C4 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
C2 C3 H3 118.1 . . ?
C4 C3 C2 123.84(17) . . ?
C4 C3 H3 118.1 . . ?
O1 C1 C2 122.87(17) . . ?
O1 C1 C7 120.96(16) . . ?
C2 C1 C7 115.98(15) . . ?
C5 C4 H4 118.1 . . ?
C3 C4 C5 123.76(17) . . ?
C3 C4 H4 118.1 . . ?
C2 C15 H15 114.8 . . ?
C2 C15 C16 130.43(18) . . ?
C16 C15 H15 114.8 . . ?
C7 C8 H8 114.7 . . ?
C7 C8 C9 130.64(18) . . ?
C9 C8 H8 114.7 . . ?
C14 C9 C8 118.5(2) . . ?
C14 C9 C10 118.3(2) . . ?
C10 C9 C8 123.12(19) . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C16 C15 124.6(2) . . ?
C17 C16 C21 118.2(2) . . ?
C21 C16 C15 117.2(2) . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C12 C11 H11 119.7 . . ?
C12 C11 C10 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(3) . . ?
C13 C12 H12 120.2 . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.6 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
F1 C25 S1 110.9(2) . . ?
F2 C25 S1 112.5(2) . . ?
F2 C25 F1 108.3(3) . . ?
F2 C25 F3 108.0(3) . . ?
F3 C25 S1 109.7(2) . . ?
F3 C25 F1 107.4(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.8 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.0 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?

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
N1 C6 C7 C1 94.25(17) . . . . ?
N1 C6 C7 C8 -92.9(2) . . . . ?
N1 C6 C5 C4 179.99(14) . . . . ?
O4 S1 C25 F1 56.9(2) . . . . ?
O4 S1 C25 F2 178.3(2) . . . . ?
O4 S1 C25 F3 -61.5(3) . . . . ?
C6 C7 C1 O1 -104.7(2) . . . . ?
C6 C7 C1 C2 80.21(19) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C6 C5 C4 C3 76.9(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C2 C15 C16 C17 -23.9(4) . . . . ?
C2 C15 C16 C21 157.7(2) . . . . ?
O2 S1 C25 F1 -62.9(2) . . . . ?
O2 S1 C25 F2 58.6(3) . . . . ?
O2 S1 C25 F3 178.7(2) . . . . ?
C7 C6 C5 C4 -55.55(19) . . . . ?
C7 C8 C9 C14 139.2(2) . . . . ?
C7 C8 C9 C10 -43.3(3) . . . . ?
C5 C6 C7 C1 -30.3(2) . . . . ?
C5 C6 C7 C8 142.60(18) . . . . ?
C3 C2 C1 O1 162.56(19) . . . . ?
C3 C2 C1 C7 -22.4(2) . . . . ?
C3 C2 C15 C16 -3.4(3) . . . . ?
C1 C2 C3 C4 -33.4(3) . . . . ?
C1 C2 C15 C16 -175.3(2) . . . . ?
C1 C7 C8 C9 172.08(19) . . . . ?
C15 C2 C3 C4 154.9(2) . . . . ?
C15 C2 C1 O1 -24.8(3) . . . . ?
C15 C2 C1 C7 150.20(17) . . . . ?
C15 C16 C17 C18 179.5(3) . . . . ?
C15 C16 C21 C20 -178.1(3) . . . . ?
O3 S1 C25 F1 177.4(2) . . . . ?
O3 S1 C25 F2 -61.2(3) . . . . ?
O3 S1 C25 F3 59.0(3) . . . . ?
C8 C7 C1 O1 81.6(2) . . . . ?
C8 C7 C1 C2 -93.5(2) . . . . ?
C8 C9 C14 C13 179.5(2) . . . . ?
C8 C9 C10 C11 -179.4(2) . . . . ?
C9 C14 C13 C12 -1.2(4) . . . . ?
C23 N1 C6 C7 -179.63(15) . . . . ?
C23 N1 C6 C5 -56.43(19) . . . . ?
C22 N1 C6 C7 -59.0(2) . . . . ?
C22 N1 C6 C5 64.2(2) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C16 C21 C20 C19 -2.1(6) . . . . ?
C24 N1 C6 C7 62.2(2) . . . . ?
C24 N1 C6 C5 -174.64(17) . . . . ?
C14 C9 C10 C11 -1.9(3) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C17 C16 C21 C20 3.5(4) . . . . ?
C17 C18 C19 C20 2.0(6) . . . . ?
C12 C11 C10 C9 1.2(4) . . . . ?
C21 C16 C17 C18 -2.2(4) . . . . ?
C18 C19 C20 C21 -0.7(6) . . . . ?
C10 C9 C14 C13 1.9(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.500 1.000 202.8 45.5 ?
2 0.500 1.000 0.500 202.8 45.5 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.789
