# 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_A1CMI
_database_code_depnum_ccdc_archive 'CCDC 2355474'
loop_
_audit_author_name
_audit_author_address
'Connor P. McLoughlin'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 F6 I O3 S2'
_chemical_formula_sum            'C10 H9 F6 I O3 S2'
_chemical_formula_weight         482.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   11.4528(12)
_cell_length_b                   9.0531(9)
_cell_length_c                   14.0965(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.756(2)
_cell_angle_gamma                90
_cell_volume                     1459.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9796
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.47

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.194
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.031
_exptl_absorpt_coefficient_mu    2.554
_shelx_estimated_absorpt_T_min   0.578
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   'Empirical, SADABS (multi-scan)'
_exptl_absorpt_correction_T_min  0.7069
_exptl_absorpt_correction_T_max  0.7899
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12715
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.675
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3344
_reflns_number_gt                3175
_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       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0211P)²+5.2773P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3344
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0645
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
I1 I 0.33694(2) 0.45356(2) 0.34490(2) 0.01965(7) Uani 1 1 d . . . . .
S1 S 0.40149(6) 0.79977(7) 0.34807(5) 0.01256(13) Uani 1 1 d . . . . .
S2 S 0.04349(6) 0.75275(10) 0.63113(5) 0.02095(16) Uani 1 1 d . . . . .
F1 F 0.90180(15) 0.6783(2) 0.37746(13) 0.0246(4) Uani 1 1 d . . . . .
F2 F -0.07437(17) 0.8190(3) 0.66642(15) 0.0374(5) Uani 1 1 d . . . . .
F3 F 0.02648(16) 0.8540(2) 0.53987(14) 0.0251(4) Uani 1 1 d . . . . .
F4 F 0.10953(18) 0.8816(3) 0.68518(16) 0.0383(5) Uani 1 1 d . . . . .
F5 F 0.05279(18) 0.6547(3) 0.72249(13) 0.0356(5) Uani 1 1 d . . . . .
F6 F -0.03181(16) 0.6295(2) 0.57925(14) 0.0277(4) Uani 1 1 d . . . . .
O1 O 0.36531(18) 0.7899(2) 0.24957(14) 0.0170(4) Uani 1 1 d . . . . .
O2 O 0.38344(19) 0.9377(2) 0.39747(15) 0.0184(4) Uani 1 1 d . . . . .
O3 O 0.16155(18) 0.6807(2) 0.59838(14) 0.0181(4) Uani 1 1 d . . . . .
C1 C 0.7859(2) 0.7031(3) 0.3724(2) 0.0177(6) Uani 1 1 d . . . . .
C2 C 0.7398(3) 0.7976(3) 0.4384(2) 0.0188(6) Uani 1 1 d . . . . .
H2 H 0.788615 0.842935 0.486350 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6201(3) 0.8239(3) 0.4323(2) 0.0167(6) Uani 1 1 d . . . . .
H3 H 0.585676 0.887923 0.476498 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5512(2) 0.7558(3) 0.36105(19) 0.0133(5) Uani 1 1 d . . . . .
C5 C 0.5997(2) 0.6604(3) 0.29531(19) 0.0136(5) Uani 1 1 d . . . . .
H5 H 0.551466 0.614899 0.246981 0.016 Uiso 1 1 calc R U . . .
C6 C 0.7191(2) 0.6332(3) 0.3017(2) 0.0160(5) Uani 1 1 d . . . . .
H6 H 0.753963 0.568013 0.258491 0.019 Uiso 1 1 calc R U . . .
C7 C 0.3227(2) 0.6635(3) 0.4122(2) 0.0135(5) Uani 1 1 d . . . . .
C8 C 0.3473(2) 0.6684(3) 0.5226(2) 0.0155(5) Uani 1 1 d . . . . .
H8A H 0.347716 0.570057 0.553335 0.019 Uiso 1 1 calc R U . . .
H8B H 0.417542 0.726086 0.542853 0.019 Uiso 1 1 calc R U . . .
C9 C 0.2319(2) 0.7533(3) 0.5299(2) 0.0158(5) Uani 1 1 d . . . . .
H9 H 0.243298 0.861061 0.542793 0.019 Uiso 1 1 calc R U . . .
C10 C 0.1958(2) 0.7194(3) 0.4256(2) 0.0161(5) Uani 1 1 d . . . . .
H10A H 0.174420 0.808071 0.387487 0.019 Uiso 1 1 calc R U . . .
H10B H 0.135390 0.641672 0.417539 0.019 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
I1 C7 2.134(3) . ?
S1 O1 1.433(2) . ?
S1 O2 1.450(2) . ?
S1 C4 1.761(3) . ?
S1 C7 1.798(3) . ?
S2 F5 1.563(2) . ?
S2 F4 1.568(2) . ?
S2 F6 1.570(2) . ?
S2 F2 1.579(2) . ?
S2 F3 1.584(2) . ?
S2 O3 1.589(2) . ?
F1 C1 1.345(3) . ?
O3 C9 1.444(3) . ?
C1 C6 1.380(4) . ?
C1 C2 1.386(4) . ?
C2 C3 1.390(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(4) . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C10 1.559(4) . ?
C7 C8 1.568(4) . ?
C8 C9 1.537(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.538(4) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
O1 S1 O2 118.57(13) . . ?
O1 S1 C4 108.75(13) . . ?
O2 S1 C4 107.77(13) . . ?
O1 S1 C7 108.41(13) . . ?
O2 S1 C7 105.25(13) . . ?
C4 S1 C7 107.60(13) . . ?
F5 S2 F4 90.56(14) . . ?
F5 S2 F6 89.68(13) . . ?
F4 S2 F6 175.52(12) . . ?
F5 S2 F2 88.94(12) . . ?
F4 S2 F2 87.93(12) . . ?
F6 S2 F2 87.60(12) . . ?
F5 S2 F3 176.69(11) . . ?
F4 S2 F3 90.09(13) . . ?
F6 S2 F3 89.42(11) . . ?
F2 S2 F3 87.84(12) . . ?
F5 S2 O3 88.93(11) . . ?
F4 S2 O3 92.82(12) . . ?
F6 S2 O3 91.66(12) . . ?
F2 S2 O3 177.75(13) . . ?
F3 S2 O3 94.29(11) . . ?
C9 O3 S2 121.12(19) . . ?
F1 C1 C6 118.3(3) . . ?
F1 C1 C2 118.3(3) . . ?
C6 C1 C2 123.4(3) . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 S1 119.4(2) . . ?
C5 C4 S1 119.0(2) . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C10 C7 C8 89.7(2) . . ?
C10 C7 S1 109.34(19) . . ?
C8 C7 S1 114.1(2) . . ?
C10 C7 I1 115.78(19) . . ?
C8 C7 I1 116.90(19) . . ?
S1 C7 I1 109.66(13) . . ?
C9 C8 C7 88.1(2) . . ?
C9 C8 H8A 114.0 . . ?
C7 C8 H8A 114.0 . . ?
C9 C8 H8B 114.0 . . ?
C7 C8 H8B 114.0 . . ?
H8A C8 H8B 111.2 . . ?
O3 C9 C8 109.1(2) . . ?
O3 C9 C10 114.5(2) . . ?
C8 C9 C10 91.6(2) . . ?
O3 C9 H9 113.2 . . ?
C8 C9 H9 113.2 . . ?
C10 C9 H9 113.2 . . ?
C9 C10 C7 88.4(2) . . ?
C9 C10 H10A 113.9 . . ?
C7 C10 H10A 113.9 . . ?
C9 C10 H10B 113.9 . . ?
C7 C10 H10B 113.9 . . ?
H10A C10 H10B 111.1 . . ?

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
F5 S2 O3 C9 -159.2(2) . . . . ?
F4 S2 O3 C9 -68.7(2) . . . . ?
F6 S2 O3 C9 111.1(2) . . . . ?
F3 S2 O3 C9 21.6(2) . . . . ?
F1 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C3 C4 S1 -175.4(2) . . . . ?
O1 S1 C4 C3 147.7(2) . . . . ?
O2 S1 C4 C3 18.0(3) . . . . ?
C7 S1 C4 C3 -95.1(2) . . . . ?
O1 S1 C4 C5 -28.1(3) . . . . ?
O2 S1 C4 C5 -157.8(2) . . . . ?
C7 S1 C4 C5 89.1(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
S1 C4 C5 C6 175.8(2) . . . . ?
F1 C1 C6 C5 -179.0(3) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
O1 S1 C7 C10 -77.4(2) . . . . ?
O2 S1 C7 C10 50.4(2) . . . . ?
C4 S1 C7 C10 165.12(19) . . . . ?
O1 S1 C7 C8 -176.14(19) . . . . ?
O2 S1 C7 C8 -48.3(2) . . . . ?
C4 S1 C7 C8 66.4(2) . . . . ?
O1 S1 C7 I1 50.50(16) . . . . ?
O2 S1 C7 I1 178.32(13) . . . . ?
C4 S1 C7 I1 -66.95(16) . . . . ?
C10 C7 C8 C9 -11.1(2) . . . . ?
S1 C7 C8 C9 100.0(2) . . . . ?
I1 C7 C8 C9 -130.15(19) . . . . ?
S2 O3 C9 C8 172.58(19) . . . . ?
S2 O3 C9 C10 -86.4(3) . . . . ?
C7 C8 C9 O3 128.0(2) . . . . ?
C7 C8 C9 C10 11.3(2) . . . . ?
O3 C9 C10 C7 -123.2(2) . . . . ?
C8 C9 C10 C7 -11.4(2) . . . . ?
C8 C7 C10 C9 11.1(2) . . . . ?
S1 C7 C10 C9 -104.5(2) . . . . ?
I1 C7 C10 C9 131.1(2) . . . . ?

_refine_diff_density_max         1.195
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_YK5F1MI
_database_code_depnum_ccdc_archive 'CCDC 2388014'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2024-09-30 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 Br F3 O3 S'
_chemical_formula_sum            'C11 H10 Br F3 O3 S'
_chemical_formula_weight         359.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.0803(3)
_cell_length_b                   14.0712(8)
_cell_length_c                   15.4400(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1321.00(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    4891
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.23

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    3.306
_shelx_estimated_absorpt_T_min   0.291
_shelx_estimated_absorpt_T_max   0.806
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3096
_exptl_absorpt_correction_T_max  0.5117
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9164
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.958
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3037
_reflns_number_gt                2454
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.999

_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       'Apex3 (2019.11-0) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
24 July, 2024
JF3238 Duo Mo  (YK05)

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+0.5292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_abs_structure_details 
; 
 Flack x determined using 864 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.010(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3037
_refine_ls_number_parameters     245
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.070
_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
Br1 Br 0.03984(9) 0.66094(4) 0.47569(4) 0.03473(17) Uani 1 1 d . . . . .
S1 S 0.1296(2) 0.57813(10) 0.65495(10) 0.0260(3) Uani 1 1 d . . . . .
C1 C 0.2060(9) 0.5701(4) 0.5430(3) 0.0290(13) Uani 1 1 d . . . . .
O1 O 0.2685(6) 0.5104(3) 0.6991(3) 0.0303(9) Uani 1 1 d . . . . .
O2 O -0.1060(6) 0.5667(3) 0.6604(3) 0.0343(10) Uani 1 1 d . . . . .
C2 C 0.4720(17) 0.5787(6) 0.5287(9) 0.0262(19) Uani 0.7 1 d D U P A 1
H2A H 0.515011 0.611546 0.474581 0.031 Uiso 0.7 1 calc R U P A 1
H2B H 0.552583 0.604412 0.579248 0.031 Uiso 0.7 1 calc R U P A 1
C3 C 0.4743(14) 0.4705(6) 0.5224(5) 0.0290(18) Uani 0.7 1 d D U P A 1
H3 H 0.520840 0.439140 0.577615 0.035 Uiso 0.7 1 calc R U P A 1
C4 C 0.2239(15) 0.4687(7) 0.5089(8) 0.032(2) Uani 0.7 1 d D U P A 1
H4A H 0.179908 0.462016 0.447488 0.038 Uiso 0.7 1 calc R U P A 1
H4B H 0.147361 0.421272 0.545488 0.038 Uiso 0.7 1 calc R U P A 1
O5 O 0.6055(10) 0.4419(4) 0.4493(4) 0.0426(15) Uani 0.7 1 d D U P A 1
C6 C 0.6151(15) 0.3489(8) 0.4330(6) 0.059(3) Uani 0.7 1 d D U P A 1
F6 F 0.7615(15) 0.3319(8) 0.3728(6) 0.117(5) Uani 0.7 1 d D U P A 1
F7 F 0.672(2) 0.2996(7) 0.5023(6) 0.098(4) Uani 0.7 1 d D U P A 1
F8 F 0.4268(12) 0.3128(4) 0.4058(4) 0.081(2) Uani 0.7 1 d D . P A 1
C2B C 0.426(4) 0.5477(14) 0.526(3) 0.027(3) Uani 0.3 1 d D U P A 2
H2B1 H 0.524372 0.560756 0.575552 0.032 Uiso 0.3 1 calc R U P A 2
H2B2 H 0.482529 0.578424 0.472783 0.032 Uiso 0.3 1 calc R U P A 2
C3B C 0.378(4) 0.4424(14) 0.5139(11) 0.028(3) Uani 0.3 1 d D U P A 2
H3B H 0.432468 0.402644 0.563133 0.034 Uiso 0.3 1 calc R U P A 2
C4B C 0.130(4) 0.4600(18) 0.518(2) 0.031(3) Uani 0.3 1 d D U P A 2
H4B1 H 0.052117 0.425496 0.564647 0.037 Uiso 0.3 1 calc R U P A 2
H4B2 H 0.052479 0.453835 0.461629 0.037 Uiso 0.3 1 calc R U P A 2
O5B O 0.4263(19) 0.4016(10) 0.4306(8) 0.044(2) Uani 0.3 1 d D U P A 2
C6B C 0.629(4) 0.3680(12) 0.4204(11) 0.059(3) Uani 0.3 1 d D U P A 2
F6B F 0.665(3) 0.3397(19) 0.3406(13) 0.102(6) Uani 0.3 1 d D U P A 2
F7B F 0.669(4) 0.2951(14) 0.4715(19) 0.101(5) Uani 0.3 1 d D U P A 2
F8B F 0.778(2) 0.4332(13) 0.4374(14) 0.118(9) Uani 0.3 1 d D . P A 2
C7 C 0.1973(8) 0.6935(4) 0.6884(3) 0.0218(11) Uani 1 1 d . . . . .
C8 C 0.0407(9) 0.7653(4) 0.6829(4) 0.0290(12) Uani 1 1 d . . . . .
H8 H -0.100799 0.752465 0.659587 0.035 Uiso 1 1 calc R U . . .
C9 C 0.0936(8) 0.8563(4) 0.7119(4) 0.0306(13) Uani 1 1 d . . . . .
H9 H -0.011151 0.906251 0.708062 0.037 Uiso 1 1 calc R U . . .
C10 C 0.2999(9) 0.8734(4) 0.7465(3) 0.0306(13) Uani 1 1 d . . . . .
H10 H 0.335761 0.935457 0.766042 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4544(10) 0.8021(4) 0.7531(3) 0.0298(12) Uani 1 1 d . . . . .
H11 H 0.595042 0.815399 0.776947 0.036 Uiso 1 1 calc R U . . .
C12 C 0.4046(8) 0.7105(4) 0.7247(4) 0.0272(12) Uani 1 1 d . . . . .
H12 H 0.509214 0.660634 0.729912 0.033 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
Br1 C1 1.933(5) . ?
S1 O2 1.444(4) . ?
S1 O1 1.444(4) . ?
S1 C7 1.753(5) . ?
S1 C1 1.793(6) . ?
C1 C2B 1.40(3) . ?
C1 C4 1.525(11) . ?
C1 C2 1.637(11) . ?
C1 C4B 1.66(3) . ?
C2 C3 1.526(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O5 1.440(9) . ?
C3 C4 1.537(12) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
O5 C6 1.334(11) . ?
C6 F6 1.310(8) . ?
C6 F7 1.321(9) . ?
C6 F8 1.321(9) . ?
C2B C3B 1.521(15) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B O5B 1.440(13) . ?
C3B C4B 1.531(16) . ?
C3B H3B 1.0000 . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
O5B C6B 1.33(2) . ?
C6B F6B 1.313(11) . ?
C6B F8B 1.313(11) . ?
C6B F7B 1.316(11) . ?
C7 C8 1.391(7) . ?
C7 C12 1.400(7) . ?
C8 C9 1.395(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 O1 118.6(2) . . ?
O2 S1 C7 108.6(2) . . ?
O1 S1 C7 109.6(2) . . ?
O2 S1 C1 107.8(3) . . ?
O1 S1 C1 105.1(2) . . ?
C7 S1 C1 106.4(3) . . ?
C4 C1 C2 87.3(6) . . ?
C2B C1 C4B 90.7(12) . . ?
C2B C1 S1 116.3(17) . . ?
C4 C1 S1 114.2(5) . . ?
C2 C1 S1 112.4(6) . . ?
C4B C1 S1 102.2(10) . . ?
C2B C1 Br1 123.2(15) . . ?
C4 C1 Br1 118.1(5) . . ?
C2 C1 Br1 113.2(5) . . ?
C4B C1 Br1 110.1(10) . . ?
S1 C1 Br1 109.9(3) . . ?
C3 C2 C1 86.8(5) . . ?
C3 C2 H2A 114.2 . . ?
C1 C2 H2A 114.2 . . ?
C3 C2 H2B 114.2 . . ?
C1 C2 H2B 114.2 . . ?
H2A C2 H2B 111.4 . . ?
O5 C3 C2 109.5(8) . . ?
O5 C3 C4 116.0(8) . . ?
C2 C3 C4 90.9(6) . . ?
O5 C3 H3 112.9 . . ?
C2 C3 H3 112.9 . . ?
C4 C3 H3 112.9 . . ?
C1 C4 C3 90.5(6) . . ?
C1 C4 H4A 113.6 . . ?
C3 C4 H4A 113.6 . . ?
C1 C4 H4B 113.6 . . ?
C3 C4 H4B 113.6 . . ?
H4A C4 H4B 110.8 . . ?
C6 O5 C3 116.4(7) . . ?
F6 C6 F7 107.6(8) . . ?
F6 C6 F8 107.0(8) . . ?
F7 C6 F8 106.4(9) . . ?
F6 C6 O5 110.1(8) . . ?
F7 C6 O5 112.0(8) . . ?
F8 C6 O5 113.5(7) . . ?
C1 C2B C3B 93.4(14) . . ?
C1 C2B H2B1 113.0 . . ?
C3B C2B H2B1 113.0 . . ?
C1 C2B H2B2 113.0 . . ?
C3B C2B H2B2 113.0 . . ?
H2B1 C2B H2B2 110.4 . . ?
O5B C3B C2B 117(2) . . ?
O5B C3B C4B 107.5(17) . . ?
C2B C3B C4B 91.5(14) . . ?
O5B C3B H3B 112.8 . . ?
C2B C3B H3B 112.8 . . ?
C4B C3B H3B 112.8 . . ?
C3B C4B C1 83.4(13) . . ?
C3B C4B H4B1 114.7 . . ?
C1 C4B H4B1 114.7 . . ?
C3B C4B H4B2 114.7 . . ?
C1 C4B H4B2 114.7 . . ?
H4B1 C4B H4B2 111.8 . . ?
C6B O5B C3B 115.9(14) . . ?
F6B C6B F8B 106.7(12) . . ?
F6B C6B F7B 107.3(12) . . ?
F8B C6B F7B 107.4(13) . . ?
F6B C6B O5B 111.7(12) . . ?
F8B C6B O5B 111.5(12) . . ?
F7B C6B O5B 112.0(12) . . ?
C8 C7 C12 121.1(5) . . ?
C8 C7 S1 119.6(4) . . ?
C12 C7 S1 119.2(4) . . ?
C7 C8 C9 119.3(5) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 119.5(5) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 121.4(5) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.1(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 118.6(5) . . ?
C11 C12 H12 120.7 . . ?
C7 C12 H12 120.7 . . ?

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
O2 S1 C1 C2B -159.4(9) . . . . ?
O1 S1 C1 C2B -31.9(9) . . . . ?
C7 S1 C1 C2B 84.3(9) . . . . ?
O2 S1 C1 C4 -80.8(5) . . . . ?
O1 S1 C1 C4 46.7(5) . . . . ?
C7 S1 C1 C4 162.9(5) . . . . ?
O2 S1 C1 C2 -178.2(4) . . . . ?
O1 S1 C1 C2 -50.7(5) . . . . ?
C7 S1 C1 C2 65.4(5) . . . . ?
O2 S1 C1 C4B -62.3(9) . . . . ?
O1 S1 C1 C4B 65.1(9) . . . . ?
C7 S1 C1 C4B -178.7(9) . . . . ?
O2 S1 C1 Br1 54.6(3) . . . . ?
O1 S1 C1 Br1 -177.9(2) . . . . ?
C7 S1 C1 Br1 -61.7(3) . . . . ?
C4 C1 C2 C3 -15.9(8) . . . . ?
S1 C1 C2 C3 99.2(6) . . . . ?
Br1 C1 C2 C3 -135.4(5) . . . . ?
C1 C2 C3 O5 133.8(7) . . . . ?
C1 C2 C3 C4 15.8(8) . . . . ?
C2 C1 C4 C3 15.8(7) . . . . ?
S1 C1 C4 C3 -97.6(6) . . . . ?
Br1 C1 C4 C3 130.8(5) . . . . ?
O5 C3 C4 C1 -129.1(7) . . . . ?
C2 C3 C4 C1 -16.9(8) . . . . ?
C2 C3 O5 C6 -177.1(8) . . . . ?
C4 C3 O5 C6 -76.1(9) . . . . ?
C3 O5 C6 F6 -171.6(8) . . . . ?
C3 O5 C6 F7 -52.0(10) . . . . ?
C3 O5 C6 F8 68.4(9) . . . . ?
C4B C1 C2B C3B -7(2) . . . . ?
S1 C1 C2B C3B 96.6(18) . . . . ?
Br1 C1 C2B C3B -122.3(13) . . . . ?
C1 C2B C3B O5B 119(2) . . . . ?
C1 C2B C3B C4B 8(2) . . . . ?
O5B C3B C4B C1 -126.1(15) . . . . ?
C2B C3B C4B C1 -7(2) . . . . ?
C2B C1 C4B C3B 7(2) . . . . ?
S1 C1 C4B C3B -109.8(12) . . . . ?
Br1 C1 C4B C3B 133.4(11) . . . . ?
C2B C3B O5B C6B 89(2) . . . . ?
C4B C3B O5B C6B -170.1(16) . . . . ?
C3B O5B C6B F6B -174.6(17) . . . . ?
C3B O5B C6B F8B -55.3(18) . . . . ?
C3B O5B C6B F7B 65.0(18) . . . . ?
O2 S1 C7 C8 -24.1(5) . . . . ?
O1 S1 C7 C8 -155.1(4) . . . . ?
C1 S1 C7 C8 91.7(5) . . . . ?
O2 S1 C7 C12 152.4(4) . . . . ?
O1 S1 C7 C12 21.4(5) . . . . ?
C1 S1 C7 C12 -91.7(5) . . . . ?
C12 C7 C8 C9 1.7(9) . . . . ?
S1 C7 C8 C9 178.2(4) . . . . ?
C7 C8 C9 C10 -0.6(8) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
C9 C10 C11 C12 0.0(9) . . . . ?
C10 C11 C12 C7 1.1(8) . . . . ?
C8 C7 C12 C11 -1.9(8) . . . . ?
S1 C7 C12 C11 -178.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2^a H2B^a O2 0.99 2.48 3.278(13) 137. 1_655 yes
C2B^b H2B1^b O2 0.99 2.60 3.53(3) 157. 1_655 yes
C4B^b H4B2^b F8B^b 0.99 1.74 2.50(3) 131. 1_455 yes
C12 H12 F6^a 0.95 2.61 3.115(9) 114. 2_665 yes
C12 H12 F6B^b 0.95 2.62 3.248(16) 124. 2_665 yes

_refine_diff_density_max         0.604
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_yk26_acmi_a
_database_code_depnum_ccdc_archive 'CCDC 2388017'
loop_
_audit_author_name
_audit_author_address
'Yannick Kraemer'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2024-09-30 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-08-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H22 O3.994 S2'
_chemical_formula_sum            'C26 H22 O3.99 S2'
_chemical_formula_weight         462.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   17.9146(4)
_cell_length_b                   9.8344(2)
_cell_length_c                   12.7724(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.3640(10)
_cell_angle_gamma                90
_cell_volume                     2220.25(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    133.00
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.628
_exptl_absorpt_coefficient_mu    2.433
_exptl_absorpt_correction_T_max  0.8042
_exptl_absorpt_correction_T_min  0.7042
_exptl_absorpt_correction_type   'Empirical, SADABS (multi-scan)'
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0768 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.8757.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             968
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0760
0.00 0.00 -1.00 0.1040
0.00 -1.00 0.00 0.0850
0.00 1.00 0.00 0.0070
1.00 0.00 0.00 0.0020
-1.00 0.00 0.00 0.0370

_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.075
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27924
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.276
_diffrn_reflns_theta_min         2.500
_diffrn_ambient_temperature      133.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  Mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3562
_reflns_number_total             4051
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00052(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4051
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.075
_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)+(0.0271P)²+1.4396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0805
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C19(H19), C12(H12), C10(H10), C13(H13), C5(H5), C16(H16), C15(H15),
 C18(H18), C3(H3), C25(H25), C22(H22), C24(H24), C26(H26), C6(H6), C1(H1),
 C2(H2), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   dual
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
S2 S 0.73139(2) 0.37698(4) 0.64268(3) 0.02237(12) Uani 1 1 d . . . . .
S1 S 0.77810(2) 0.18450(4) 0.67608(3) 0.02256(12) Uani 1 1 d . . . . .
O1 O 0.97587(7) 0.12313(13) 0.35108(9) 0.0254(3) Uani 1 1 d . . . . .
O4 O 0.51714(7) 0.34411(14) 0.24306(10) 0.0292(3) Uani 1 1 d . . . . .
O2 O 0.79052(7) 0.46674(13) 0.62197(10) 0.0295(5) Uani 1.000(5) 1 d . . . . .
O3 O 0.69158(7) 0.40454(14) 0.72962(10) 0.0301(5) Uani 0.995(5) 1 d . . . . .
C8 C 0.93422(10) 0.13893(18) 0.43084(13) 0.0213(4) Uani 1 1 d . . . . .
C9 C 0.96090(10) 0.19770(18) 0.52880(13) 0.0228(4) Uani 1 1 d . . . . .
H9 H 1.012015 0.226849 0.545495 0.027 Uiso 1 1 calc R U . . .
C19 C 0.69013(10) 0.37811(18) 0.42795(14) 0.0233(4) Uani 1 1 d . . . . .
H19 H 0.742248 0.392162 0.425229 0.028 Uiso 1 1 calc R U . . .
C17 C 0.56180(10) 0.34974(18) 0.34018(14) 0.0224(4) Uani 1 1 d . . . . .
C14 C 0.66511(10) 0.36400(17) 0.52528(13) 0.0214(4) Uani 1 1 d . . . . .
C4 C 1.08689(10) 0.15196(18) 0.27165(13) 0.0222(4) Uani 1 1 d . . . . .
C12 C 0.81121(10) 0.10721(18) 0.48061(14) 0.0235(4) Uani 1 1 d . . . . .
H12 H 0.760544 0.075478 0.464687 0.028 Uiso 1 1 calc R U . . .
C7 C 1.05296(10) 0.1684(2) 0.37125(14) 0.0247(4) Uani 1 1 d . . . . .
H7A H 1.081981 0.114084 0.429323 0.030 Uiso 1 1 calc R U . . .
H7B H 1.055084 0.265021 0.393218 0.030 Uiso 1 1 calc R U . . .
C10 C 0.91202(10) 0.21338(18) 0.60208(14) 0.0224(4) Uani 1 1 d . . . . .
H10 H 0.929632 0.254944 0.668659 0.027 Uiso 1 1 calc R U . . .
C13 C 0.85945(10) 0.09311(18) 0.40735(14) 0.0233(4) Uani 1 1 d . . . . .
H13 H 0.841777 0.052056 0.340591 0.028 Uiso 1 1 calc R U . . .
C21 C 0.40207(10) 0.34460(19) 0.12293(14) 0.0243(4) Uani 1 1 d . . . . .
C11 C 0.83749(10) 0.16862(18) 0.57857(13) 0.0214(4) Uani 1 1 d . . . . .
C5 C 1.06860(11) 0.04283(19) 0.20283(14) 0.0271(4) Uani 1 1 d . . . . .
H5 H 1.032476 -0.022572 0.216870 0.033 Uiso 1 1 calc R U . . .
C16 C 0.53679(10) 0.33412(19) 0.43708(14) 0.0248(4) Uani 1 1 d . . . . .
H16 H 0.484786 0.318485 0.439631 0.030 Uiso 1 1 calc R U . . .
C15 C 0.58906(10) 0.34173(18) 0.53003(14) 0.0241(4) Uani 1 1 d . . . . .
H15 H 0.572860 0.331730 0.596829 0.029 Uiso 1 1 calc R U . . .
C18 C 0.63838(10) 0.37140(19) 0.33620(14) 0.0244(4) Uani 1 1 d . . . . .
H18 H 0.654741 0.381543 0.269511 0.029 Uiso 1 1 calc R U . . .
C3 C 1.13959(10) 0.24683(19) 0.24918(14) 0.0271(4) Uani 1 1 d . . . . .
H3 H 1.151922 0.322391 0.295071 0.032 Uiso 1 1 calc R U . . .
C25 C 0.32298(11) 0.2570(2) -0.03337(15) 0.0310(4) Uani 1 1 d . . . . .
H25 H 0.291332 0.186993 -0.067191 0.037 Uiso 1 1 calc R U . . .
C22 C 0.41490(11) 0.4603(2) 0.06601(15) 0.0307(4) Uani 1 1 d . . . . .
H22 H 0.446145 0.530851 0.099830 0.037 Uiso 1 1 calc R U . . .
C20 C 0.43654(10) 0.3322(2) 0.23797(15) 0.0294(4) Uani 1 1 d . . . . .
H20A H 0.417497 0.405277 0.280008 0.035 Uiso 1 1 calc R U . . .
H20B H 0.423600 0.243282 0.266567 0.035 Uiso 1 1 calc R U . . .
C24 C 0.33565(10) 0.3725(2) -0.08886(14) 0.0281(4) Uani 1 1 d . . . . .
H24 H 0.312314 0.382814 -0.160713 0.034 Uiso 1 1 calc R U . . .
C26 C 0.35653(10) 0.2428(2) 0.07224(15) 0.0289(4) Uani 1 1 d . . . . .
H26 H 0.348085 0.162493 0.109913 0.035 Uiso 1 1 calc R U . . .
C6 C 1.10328(12) 0.0296(2) 0.11341(15) 0.0320(4) Uani 1 1 d . . . . .
H6 H 1.090393 -0.044573 0.066293 0.038 Uiso 1 1 calc R U . . .
C1 C 1.15644(11) 0.1238(2) 0.09265(15) 0.0311(4) Uani 1 1 d . . . . .
H1 H 1.180405 0.113699 0.031999 0.037 Uiso 1 1 calc R U . . .
C2 C 1.17441(11) 0.2322(2) 0.16022(15) 0.0310(4) Uani 1 1 d . . . . .
H2 H 1.210708 0.297161 0.146020 0.037 Uiso 1 1 calc R U . . .
C23 C 0.38262(11) 0.4737(2) -0.03943(16) 0.0318(4) Uani 1 1 d . . . . .
H23 H 0.392614 0.552305 -0.078079 0.038 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
S2 S1 2.0855(6) . ?
S2 O2 1.4362(13) . ?
S2 O3 1.4398(13) . ?
S2 C14 1.7592(18) . ?
S1 C11 1.7717(17) . ?
O1 C8 1.366(2) . ?
O1 C7 1.434(2) . ?
O4 C17 1.363(2) . ?
O4 C20 1.439(2) . ?
C8 C9 1.390(2) . ?
C8 C13 1.399(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(2) . ?
C19 H19 0.9500 . ?
C19 C14 1.395(2) . ?
C19 C18 1.372(3) . ?
C17 C16 1.392(2) . ?
C17 C18 1.398(2) . ?
C14 C15 1.391(2) . ?
C4 C7 1.505(2) . ?
C4 C5 1.392(3) . ?
C4 C3 1.390(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(2) . ?
C12 C11 1.400(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C11 1.391(2) . ?
C13 H13 0.9500 . ?
C21 C22 1.389(3) . ?
C21 C20 1.503(3) . ?
C21 C26 1.384(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C18 H18 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.390(3) . ?
C25 H25 0.9500 . ?
C25 C24 1.377(3) . ?
C25 C26 1.392(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C24 H24 0.9500 . ?
C24 C23 1.387(3) . ?
C26 H26 0.9500 . ?
C6 H6 0.9500 . ?
C6 C1 1.385(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.376(3) . ?
C2 H2 0.9500 . ?
C23 H23 0.9500 . ?

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 S2 S1 108.18(6) . . ?
O2 S2 O3 119.94(8) . . ?
O2 S2 C14 107.66(8) . . ?
O3 S2 S1 104.23(6) . . ?
O3 S2 C14 108.71(8) . . ?
C14 S2 S1 107.53(6) . . ?
C11 S1 S2 101.72(6) . . ?
C8 O1 C7 117.24(13) . . ?
C17 O4 C20 118.70(14) . . ?
O1 C8 C9 124.67(16) . . ?
O1 C8 C13 115.06(15) . . ?
C9 C8 C13 120.26(16) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.33(16) . . ?
C10 C9 H9 120.3 . . ?
C14 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C18 C19 C14 119.06(16) . . ?
O4 C17 C16 125.34(16) . . ?
O4 C17 C18 114.04(15) . . ?
C16 C17 C18 120.61(16) . . ?
C19 C14 S2 118.82(13) . . ?
C15 C14 S2 120.28(13) . . ?
C15 C14 C19 120.89(16) . . ?
C5 C4 C7 122.03(16) . . ?
C3 C4 C7 118.93(16) . . ?
C3 C4 C5 119.02(16) . . ?
C13 C12 H12 120.2 . . ?
C13 C12 C11 119.51(16) . . ?
C11 C12 H12 120.2 . . ?
O1 C7 C4 108.94(14) . . ?
O1 C7 H7A 109.9 . . ?
O1 C7 H7B 109.9 . . ?
C4 C7 H7A 109.9 . . ?
C4 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.46(16) . . ?
C11 C10 H10 119.8 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.38(16) . . ?
C12 C13 H13 119.8 . . ?
C22 C21 C20 120.06(17) . . ?
C26 C21 C22 118.86(17) . . ?
C26 C21 C20 121.07(17) . . ?
C12 C11 S1 120.87(14) . . ?
C10 C11 S1 119.04(13) . . ?
C10 C11 C12 120.05(16) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.96(18) . . ?
C6 C5 H5 120.0 . . ?
C17 C16 H16 120.5 . . ?
C15 C16 C17 118.96(16) . . ?
C15 C16 H16 120.5 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.00(16) . . ?
C16 C15 H15 120.0 . . ?
C19 C18 C17 120.46(16) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.63(18) . . ?
C2 C3 H3 119.7 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.01(18) . . ?
C26 C25 H25 120.0 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.59(18) . . ?
C23 C22 H22 119.7 . . ?
O4 C20 C21 106.69(14) . . ?
O4 C20 H20A 110.4 . . ?
O4 C20 H20B 110.4 . . ?
C21 C20 H20A 110.4 . . ?
C21 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
C25 C24 H24 120.1 . . ?
C25 C24 C23 119.74(17) . . ?
C23 C24 H24 120.1 . . ?
C21 C26 C25 120.66(18) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C5 C6 H6 119.8 . . ?
C1 C6 C5 120.47(18) . . ?
C1 C6 H6 119.8 . . ?
C6 C1 H1 120.1 . . ?
C2 C1 C6 119.73(17) . . ?
C2 C1 H1 120.1 . . ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.18(18) . . ?
C1 C2 H2 119.9 . . ?
C22 C23 C24 120.11(18) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?

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
S2 S1 C11 C12 -92.67(15) . . . . ?
S2 S1 C11 C10 89.83(14) . . . . ?
S2 C14 C15 C16 178.80(14) . . . . ?
S1 S2 C14 C19 -86.63(14) . . . . ?
S1 S2 C14 C15 94.15(14) . . . . ?
O1 C8 C9 C10 177.27(16) . . . . ?
O1 C8 C13 C12 -178.15(16) . . . . ?
O4 C17 C16 C15 179.69(17) . . . . ?
O4 C17 C18 C19 -179.40(16) . . . . ?
O2 S2 C14 C19 29.73(16) . . . . ?
O2 S2 C14 C15 -149.49(14) . . . . ?
O3 S2 C14 C19 161.09(14) . . . . ?
O3 S2 C14 C15 -18.13(17) . . . . ?
C8 O1 C7 C4 -175.76(14) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
C9 C10 C11 S1 177.56(13) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C19 C14 C15 C16 -0.4(3) . . . . ?
C17 O4 C20 C21 173.63(15) . . . . ?
C17 C16 C15 C14 -0.3(3) . . . . ?
C14 C19 C18 C17 -0.5(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C7 O1 C8 C9 1.2(2) . . . . ?
C7 O1 C8 C13 -179.92(15) . . . . ?
C7 C4 C5 C6 -177.94(17) . . . . ?
C7 C4 C3 C2 177.43(17) . . . . ?
C13 C8 C9 C10 -1.5(3) . . . . ?
C13 C12 C11 S1 -178.30(13) . . . . ?
C13 C12 C11 C10 -0.8(3) . . . . ?
C21 C22 C23 C24 1.4(3) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C5 C4 C7 O1 -36.4(2) . . . . ?
C5 C4 C3 C2 -0.9(3) . . . . ?
C5 C6 C1 C2 -0.8(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C18 C19 C14 S2 -178.42(14) . . . . ?
C18 C19 C14 C15 0.8(3) . . . . ?
C18 C17 C16 C15 0.6(3) . . . . ?
C3 C4 C7 O1 145.33(16) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C25 C24 C23 C22 -1.8(3) . . . . ?
C22 C21 C20 O4 -58.2(2) . . . . ?
C22 C21 C26 C25 -1.2(3) . . . . ?
C20 O4 C17 C16 5.4(3) . . . . ?
C20 O4 C17 C18 -175.47(16) . . . . ?
C20 C21 C22 C23 -179.07(18) . . . . ?
C20 C21 C26 C25 178.01(17) . . . . ?
C24 C25 C26 C21 0.7(3) . . . . ?
C26 C21 C22 C23 0.1(3) . . . . ?
C26 C21 C20 O4 122.62(18) . . . . ?
C26 C25 C24 C23 0.7(3) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'




####################################################################### 
# 
# 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_yk37_final_a
_database_code_depnum_ccdc_archive 'CCDC 2403288'
loop_
_audit_author_name
_audit_author_address
'Yannick Kraemer'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2024-11-16 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-10-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 Br F2 O2 S'
_chemical_formula_sum            'C10 H9 Br F2 O2 S'
_chemical_formula_weight         311.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.0400(11)
_cell_length_b                   8.6290(10)
_cell_length_c                   14.2763(16)
_cell_angle_alpha                90
_cell_angle_beta                 109.979(2)
_cell_angle_gamma                90
_cell_volume                     1162.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8365
_cell_measurement_temperature    90.15
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.454
_shelx_estimated_absorpt_T_min   0.221
_exptl_absorpt_coefficient_mu    3.724
_exptl_absorpt_correction_T_max  0.3287
_exptl_absorpt_correction_T_min  0.2093
_exptl_absorpt_correction_type   'Empirical, SADABS (multi-scan)'
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1345 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.6368.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 -3.00 0.2420
1.00 0.00 3.00 0.2420
-1.00 5.00 2.00 0.2430
1.00 -5.00 -2.00 0.2510
-1.00 0.00 1.00 0.0570
1.00 0.00 -1.00 0.1260
4.00 -2.00 -1.00 0.1960
-1.00 4.00 -4.00 0.2920
1.00 -2.00 2.00 0.2660

_exptl_crystal_size_max          0.582
_exptl_crystal_size_mid          0.484
_exptl_crystal_size_min          0.252
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16237
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.558
_diffrn_reflns_theta_min         2.173
_diffrn_ambient_temperature      90.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Duo APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3119
_reflns_number_total             3553
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.049
_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)+(0.0376P)²+0.3194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0688
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C7(H7), C6(H6), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br 0.65001(2) 0.31212(2) 0.49696(2) 0.02138(6) Uani 1 1 d . . . . .
S1 S 0.40480(4) 0.19536(4) 0.31859(3) 0.01503(8) Uani 1 1 d . . . . .
F1 F 0.63494(13) 0.58977(13) 0.21623(10) 0.0390(3) Uani 1 1 d . . . . .
O2 O 0.32541(13) 0.22986(13) 0.21542(8) 0.0207(2) Uani 1 1 d . . . . .
O1 O 0.47015(13) 0.04490(12) 0.34313(9) 0.0205(2) Uani 1 1 d . . . . .
F2 F 0.03005(14) 0.29531(14) 0.54833(10) 0.0397(3) Uani 1 1 d . . . . .
C5 C 0.29350(16) 0.22629(17) 0.38905(12) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.54457(17) 0.33837(17) 0.35690(12) 0.0165(3) Uani 1 1 d . . . . .
C10 C 0.17946(18) 0.32767(17) 0.35220(13) 0.0202(3) Uani 1 1 d . . . . .
H10 H 0.162960 0.379505 0.290553 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2289(2) 0.1693(2) 0.53255(14) 0.0265(4) Uani 1 1 d . . . . .
H7 H 0.243753 0.116188 0.593589 0.032 Uiso 1 1 calc R U . . .
C2 C 0.62998(18) 0.33037(19) 0.28439(13) 0.0218(3) Uani 1 1 d . . . . .
H2A H 0.732969 0.348115 0.316894 0.026 Uiso 1 1 calc R U . . .
H2B H 0.611433 0.235978 0.242468 0.026 Uiso 1 1 calc R U . . .
C6 C 0.31858(18) 0.14600(19) 0.47809(13) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.396084 0.076152 0.501356 0.026 Uiso 1 1 calc R U . . .
C9 C 0.09015(19) 0.3520(2) 0.40673(15) 0.0256(3) Uani 1 1 d . . . . .
H9 H 0.012534 0.421801 0.383818 0.031 Uiso 1 1 calc R U . . .
C8 C 0.11729(19) 0.2719(2) 0.49531(14) 0.0262(4) Uani 1 1 d . . . . .
C4 C 0.49521(17) 0.50424(17) 0.31910(13) 0.0196(3) Uani 1 1 d . . . . .
H4A H 0.391525 0.519864 0.299023 0.024 Uiso 1 1 calc R U . . .
H4B H 0.547531 0.587407 0.364625 0.024 Uiso 1 1 calc R U . . .
C1 C 0.54763(19) 0.47378(19) 0.23136(14) 0.0237(3) Uani 1 1 d . . . . .
H1 H 0.468530 0.446462 0.168759 0.028 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
Br1 C3 1.9297(16) . ?
S1 O2 1.4460(12) . ?
S1 O1 1.4429(11) . ?
S1 C5 1.7606(16) . ?
S1 C3 1.8074(16) . ?
F1 C1 1.3951(18) . ?
F2 C8 1.354(2) . ?
C5 C10 1.393(2) . ?
C5 C6 1.393(2) . ?
C3 C2 1.555(2) . ?
C3 C4 1.550(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.390(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.391(2) . ?
C7 C8 1.384(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.536(2) . ?
C6 H6 0.9500 . ?
C9 H9 0.9500 . ?
C9 C8 1.384(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C1 1.538(2) . ?
C1 H1 1.0000 . ?

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 C5 108.31(7) . . ?
O2 S1 C3 105.57(7) . . ?
O1 S1 O2 118.64(7) . . ?
O1 S1 C5 108.81(7) . . ?
O1 S1 C3 107.41(7) . . ?
C5 S1 C3 107.60(7) . . ?
C10 C5 S1 118.66(12) . . ?
C6 C5 S1 119.60(12) . . ?
C6 C5 C10 121.72(15) . . ?
S1 C3 Br1 109.13(8) . . ?
C2 C3 Br1 116.90(11) . . ?
C2 C3 S1 108.42(11) . . ?
C4 C3 Br1 117.78(10) . . ?
C4 C3 S1 113.72(11) . . ?
C4 C3 C2 89.58(12) . . ?
C5 C10 H10 120.4 . . ?
C9 C10 C5 119.19(15) . . ?
C9 C10 H10 120.4 . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C8 C7 C6 118.13(16) . . ?
C3 C2 H2A 114.0 . . ?
C3 C2 H2B 114.0 . . ?
H2A C2 H2B 111.2 . . ?
C1 C2 C3 88.05(12) . . ?
C1 C2 H2A 114.0 . . ?
C1 C2 H2B 114.0 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.25(15) . . ?
C7 C6 H6 120.4 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 C10 118.23(16) . . ?
C8 C9 H9 120.9 . . ?
F2 C8 C7 118.28(16) . . ?
F2 C8 C9 118.25(16) . . ?
C7 C8 C9 123.47(16) . . ?
C3 C4 H4A 114.0 . . ?
C3 C4 H4B 114.0 . . ?
H4A C4 H4B 111.2 . . ?
C1 C4 C3 88.17(11) . . ?
C1 C4 H4A 114.0 . . ?
C1 C4 H4B 114.0 . . ?
F1 C1 C2 113.17(14) . . ?
F1 C1 C4 114.30(14) . . ?
F1 C1 H1 112.3 . . ?
C2 C1 C4 90.72(13) . . ?
C2 C1 H1 112.3 . . ?
C4 C1 H1 112.3 . . ?

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
Br1 C3 C2 C1 -135.24(11) . . . . ?
Br1 C3 C4 C1 134.47(12) . . . . ?
S1 C5 C10 C9 179.46(13) . . . . ?
S1 C5 C6 C7 -179.01(13) . . . . ?
S1 C3 C2 C1 100.95(12) . . . . ?
S1 C3 C4 C1 -96.03(12) . . . . ?
O2 S1 C5 C10 -24.12(14) . . . . ?
O2 S1 C5 C6 153.93(13) . . . . ?
O2 S1 C3 Br1 176.05(7) . . . . ?
O2 S1 C3 C2 -55.61(12) . . . . ?
O2 S1 C3 C4 42.32(13) . . . . ?
O1 S1 C5 C10 -154.37(12) . . . . ?
O1 S1 C5 C6 23.69(15) . . . . ?
O1 S1 C3 Br1 -56.44(9) . . . . ?
O1 S1 C3 C2 71.90(12) . . . . ?
O1 S1 C3 C4 169.83(10) . . . . ?
C5 S1 C3 Br1 60.55(9) . . . . ?
C5 S1 C3 C2 -171.11(10) . . . . ?
C5 S1 C3 C4 -73.18(12) . . . . ?
C5 C10 C9 C8 -1.0(3) . . . . ?
C3 S1 C5 C10 89.56(14) . . . . ?
C3 S1 C5 C6 -92.39(14) . . . . ?
C3 C2 C1 F1 131.03(15) . . . . ?
C3 C2 C1 C4 14.10(12) . . . . ?
C3 C4 C1 F1 -130.08(15) . . . . ?
C3 C4 C1 C2 -14.14(12) . . . . ?
C10 C5 C6 C7 -1.0(3) . . . . ?
C10 C9 C8 F2 -179.81(16) . . . . ?
C10 C9 C8 C7 0.2(3) . . . . ?
C2 C3 C4 C1 13.97(13) . . . . ?
C6 C5 C10 C9 1.4(2) . . . . ?
C6 C7 C8 F2 -179.76(17) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C8 C7 C6 C5 0.2(3) . . . . ?
C4 C3 C2 C1 -13.98(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_yk20_acmi_a
_database_code_depnum_ccdc_archive 'CCDC 2388016'
loop_
_audit_author_name
_audit_author_address
'Yannick Kraemer'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2024-09-30 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-07-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 F3 O4 S'
_chemical_formula_sum            'C18 H17 F3 O4 S'
_chemical_formula_weight         386.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   18.4827(6)
_cell_length_b                   8.7216(3)
_cell_length_c                   11.2089(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.3180(10)
_cell_angle_gamma                90
_cell_volume                     1750.74(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9428
_cell_measurement_temperature    133.00
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9377
_exptl_absorpt_correction_T_min  0.8762
_exptl_absorpt_correction_type   'Empirical, SADABS (multi-scan)'
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1124 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.9344.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 0.00 0.0320
-1.00 1.00 1.00 0.0740
1.00 -1.00 -1.00 0.0680
0.00 1.00 -1.00 0.0880
0.00 -1.00 1.00 0.0360
5.00 0.00 -3.00 0.1200
-5.00 0.00 3.00 0.0470
-2.00 1.00 0.00 0.0850
-2.00 0.00 -1.00 0.0410
2.00 0.00 1.00 0.0530
2.00 1.00 -1.00 0.1080
-1.00 -2.00 -2.00 0.0440
1.00 1.00 2.00 0.0520

_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.109
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26827
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.372
_diffrn_reflns_theta_min         2.274
_diffrn_ambient_temperature      133.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  Mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2498
_reflns_number_total             3207
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0053(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3207
_refine_ls_number_restraints     167
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.146
_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)+(0.0609P)²+3.6058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1552
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O1A-C2 \\sim O1-C2
 with sigma of 0.003
 O1-C1 \\sim O1A-C1A
 with sigma of 0.003
 F1A-C1A \\sim F3A-C1A \\sim F1-C1 \\sim F2-C1 \\sim F2A-C1A \\sim F3-C1
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
O1A \\sim O1: within 2A with sigma of 0.003 and sigma for terminal atoms of
0.006 within 2A
F1 \\sim O1 \\sim F3 \\sim F2 \\sim C1 \\sim F1A \\sim F3A \\sim F2A \\sim C1A
\\sim O1A \\sim C2: within 2A with sigma of 0.003 and sigma for terminal atoms
of 0.006 within 2A
4. Others
 Sof(F1A)=Sof(F3A)=Sof(F2A)=Sof(C1A)=Sof(O1A)=1-FVAR(1)
 Sof(F1)=Sof(O1)=Sof(F3)=Sof(F2)=Sof(C1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C5(H5A,H5B), C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C8(H8), C11(H11), C18(H18), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.65406(4) 0.63237(9) 0.30759(7) 0.0250(2) Uani 1 1 d . . . . .
O4 O 0.37283(11) 0.6987(2) 0.45838(19) 0.0233(5) Uani 1 1 d . . . . .
O2 O 0.67407(13) 0.7836(3) 0.2760(2) 0.0334(6) Uani 1 1 d . . . . .
O3 O 0.64120(13) 0.5157(3) 0.2137(2) 0.0395(6) Uani 1 1 d . . . . .
F1 F 0.9992(2) 0.8049(5) 0.6549(4) 0.0576(11) Uani 0.746(4) 1 d D U P A 1
O1 O 0.8996(6) 0.6970(19) 0.5524(11) 0.0495(9) Uani 0.746(4) 1 d D U P A 1
C7 C 0.56751(17) 0.7595(3) 0.4468(3) 0.0238(7) Uani 1 1 d . . . . .
H7 H 0.609154 0.823827 0.479681 0.029 Uiso 1 1 calc R U . . .
C9 C 0.44099(17) 0.6848(3) 0.4336(3) 0.0217(7) Uani 1 1 d . . . . .
C10 C 0.44745(17) 0.5670(3) 0.3522(3) 0.0222(7) Uani 1 1 d . . . . .
H10 H 0.406451 0.500412 0.320976 0.027 Uiso 1 1 calc R U . . .
C8 C 0.50220(17) 0.7790(3) 0.4832(3) 0.0226(7) Uani 1 1 d . . . . .
H8 H 0.498798 0.855808 0.541686 0.027 Uiso 1 1 calc R U . . .
C11 C 0.51352(17) 0.5475(3) 0.3171(3) 0.0227(7) Uani 1 1 d . . . . .
H11 H 0.518308 0.466801 0.262667 0.027 Uiso 1 1 calc R U . . .
C6 C 0.57280(17) 0.6464(3) 0.3620(3) 0.0223(7) Uani 1 1 d . . . . .
C13 C 0.27876(18) 0.8452(3) 0.5201(3) 0.0249(7) Uani 1 1 d . . . . .
C12 C 0.36101(18) 0.8259(4) 0.5332(3) 0.0262(7) Uani 1 1 d . . . . .
H12A H 0.382009 0.920629 0.506478 0.031 Uiso 1 1 calc R U . . .
H12B H 0.386567 0.806545 0.620439 0.031 Uiso 1 1 calc R U . . .
C18 C 0.25149(19) 0.8750(4) 0.6216(3) 0.0322(8) Uani 1 1 d . . . . .
H18 H 0.284729 0.878549 0.701162 0.039 Uiso 1 1 calc R U . . .
C4 C 0.72499(17) 0.5669(4) 0.4326(3) 0.0279(7) Uani 1 1 d . . . . .
H4 H 0.708871 0.471169 0.467864 0.033 Uiso 1 1 calc R U . . .
C5 C 0.80241(18) 0.5442(4) 0.4064(3) 0.0347(8) Uani 1 1 d . . . . .
H5A H 0.814521 0.436308 0.392060 0.042 Uiso 1 1 calc R U . . .
H5B H 0.812350 0.612746 0.341869 0.042 Uiso 1 1 calc R U . . .
C2 C 0.83496(19) 0.6002(5) 0.5373(4) 0.0382(8) Uani 1 1 d D U . . .
F3 F 0.9752(2) 0.5751(5) 0.7047(4) 0.0748(12) Uani 0.746(4) 1 d D U P A 1
C14 C 0.22939(19) 0.8423(4) 0.4046(3) 0.0350(8) Uani 1 1 d . . . . .
H14 H 0.247631 0.824191 0.333694 0.042 Uiso 1 1 calc R U . . .
C3 C 0.76107(19) 0.6791(4) 0.5361(3) 0.0361(8) Uani 1 1 d . . . . .
H3A H 0.758661 0.787976 0.510387 0.043 Uiso 1 1 calc R U . . .
H3B H 0.744359 0.665808 0.612873 0.043 Uiso 1 1 calc R U . . .
C15 C 0.1540(2) 0.8656(5) 0.3918(4) 0.0438(10) Uani 1 1 d . . . . .
H15 H 0.120545 0.861431 0.312410 0.053 Uiso 1 1 calc R U . . .
C16 C 0.1270(2) 0.8949(5) 0.4934(4) 0.0424(9) Uani 1 1 d . . . . .
H16 H 0.075088 0.911448 0.484443 0.051 Uiso 1 1 calc R U . . .
C17 C 0.1757(2) 0.8999(4) 0.6082(4) 0.0423(9) Uani 1 1 d . . . . .
H17 H 0.157394 0.920614 0.678605 0.051 Uiso 1 1 calc R U . . .
F2 F 0.9085(2) 0.7677(5) 0.7350(4) 0.0815(12) Uani 0.746(4) 1 d D U P A 1
C1 C 0.9448(3) 0.7069(4) 0.6578(5) 0.0585(10) Uani 0.746(4) 1 d D U P A 1
F1A F 1.0106(8) 0.7597(18) 0.6274(15) 0.066(2) Uani 0.254(4) 1 d D U P A 2
F3A F 0.9825(6) 0.5443(14) 0.6007(12) 0.0758(18) Uani 0.254(4) 1 d D U P A 2
F2A F 0.9519(7) 0.6362(17) 0.7494(10) 0.0738(18) Uani 0.254(4) 1 d D U P A 2
C1A C 0.9534(9) 0.6713(14) 0.6347(11) 0.0594(11) Uani 0.254(4) 1 d D U P A 2
O1A O 0.8989(16) 0.697(6) 0.543(3) 0.0504(11) Uani 0.254(4) 1 d D U P A 2
H2 H 0.849(2) 0.513(5) 0.597(3) 0.044(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.438(2) . ?
S1 O3 1.441(2) . ?
S1 C6 1.760(3) . ?
S1 C4 1.761(3) . ?
O4 C9 1.361(4) . ?
O4 C12 1.439(4) . ?
F1 C1 1.326(3) . ?
O1 C2 1.439(4) . ?
O1 C1 1.270(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(4) . ?
C7 C6 1.389(4) . ?
C9 C10 1.399(4) . ?
C9 C8 1.397(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(4) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C11 C6 1.388(4) . ?
C13 C12 1.500(4) . ?
C13 C18 1.379(5) . ?
C13 C14 1.387(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C18 H18 0.9500 . ?
C18 C17 1.388(5) . ?
C4 H4 1.0000 . ?
C4 C5 1.543(4) . ?
C4 C3 1.538(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C2 1.521(5) . ?
C2 C3 1.527(5) . ?
C2 O1A 1.438(5) . ?
C2 H2 1.00(4) . ?
F3 C1 1.330(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C16 1.376(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(5) . ?
C17 H17 0.9500 . ?
F2 C1 1.329(3) . ?
F1A C1A 1.327(3) . ?
F3A C1A 1.328(3) . ?
F2A C1A 1.329(3) . ?
C1A O1A 1.269(8) . ?

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 O3 118.32(15) . . ?
O2 S1 C6 108.36(14) . . ?
O2 S1 C4 107.89(15) . . ?
O3 S1 C6 107.58(14) . . ?
O3 S1 C4 107.95(16) . . ?
C6 S1 C4 106.13(15) . . ?
C9 O4 C12 118.0(2) . . ?
C1 O1 C2 119.0(6) . . ?
C8 C7 H7 119.8 . . ?
C8 C7 C6 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
O4 C9 C10 115.5(3) . . ?
O4 C9 C8 124.5(3) . . ?
C8 C9 C10 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C7 C8 C9 119.5(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C6 119.6(3) . . ?
C6 C11 H11 120.2 . . ?
C7 C6 S1 119.8(2) . . ?
C11 C6 S1 119.7(2) . . ?
C11 C6 C7 120.4(3) . . ?
C18 C13 C12 120.6(3) . . ?
C18 C13 C14 118.9(3) . . ?
C14 C13 C12 120.4(3) . . ?
O4 C12 C13 109.0(2) . . ?
O4 C12 H12A 109.9 . . ?
O4 C12 H12B 109.9 . . ?
C13 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C13 C18 H18 119.8 . . ?
C13 C18 C17 120.3(3) . . ?
C17 C18 H18 119.8 . . ?
S1 C4 H4 110.4 . . ?
C5 C4 S1 115.7(2) . . ?
C5 C4 H4 110.4 . . ?
C3 C4 S1 119.5(2) . . ?
C3 C4 H4 110.4 . . ?
C3 C4 C5 88.6(2) . . ?
C4 C5 H5A 114.2 . . ?
C4 C5 H5B 114.2 . . ?
H5A C5 H5B 111.4 . . ?
C2 C5 C4 86.5(3) . . ?
C2 C5 H5A 114.2 . . ?
C2 C5 H5B 114.2 . . ?
O1 C2 C5 114.9(7) . . ?
O1 C2 C3 116.9(9) . . ?
O1 C2 H2 107(2) . . ?
C5 C2 C3 89.8(3) . . ?
C5 C2 H2 112(2) . . ?
C3 C2 H2 115(2) . . ?
O1A C2 C5 110.7(18) . . ?
O1A C2 C3 117(2) . . ?
O1A C2 H2 110(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C4 C3 H3A 114.2 . . ?
C4 C3 H3B 114.2 . . ?
C2 C3 C4 86.5(3) . . ?
C2 C3 H3A 114.2 . . ?
C2 C3 H3B 114.2 . . ?
H3A C3 H3B 111.4 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.5(3) . . ?
C17 C16 H16 120.3 . . ?
C18 C17 H17 119.8 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
F1 C1 F3 108.5(4) . . ?
F1 C1 F2 105.5(4) . . ?
O1 C1 F1 110.4(4) . . ?
O1 C1 F3 115.2(9) . . ?
O1 C1 F2 108.2(10) . . ?
F2 C1 F3 108.6(5) . . ?
F1A C1A F3A 94.6(12) . . ?
F1A C1A F2A 113.6(14) . . ?
F3A C1A F2A 101.1(13) . . ?
O1A C1A F1A 109.5(10) . . ?
O1A C1A F3A 102(3) . . ?
O1A C1A F2A 129(2) . . ?
C1A O1A C2 114.3(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
S1 C4 C5 C2 144.1(3) . . . . ?
S1 C4 C3 C2 -140.6(3) . . . . ?
O4 C9 C10 C11 177.3(3) . . . . ?
O4 C9 C8 C7 -176.6(3) . . . . ?
O2 S1 C6 C7 -45.8(3) . . . . ?
O2 S1 C6 C11 132.2(2) . . . . ?
O2 S1 C4 C5 -64.5(3) . . . . ?
O2 S1 C4 C3 39.5(3) . . . . ?
O3 S1 C6 C7 -174.8(2) . . . . ?
O3 S1 C6 C11 3.2(3) . . . . ?
O3 S1 C4 C5 64.5(3) . . . . ?
O3 S1 C4 C3 168.4(2) . . . . ?
O1 C2 C3 C4 140.0(6) . . . . ?
C9 O4 C12 C13 164.4(2) . . . . ?
C9 C10 C11 C6 -0.8(4) . . . . ?
C10 C9 C8 C7 3.1(4) . . . . ?
C10 C11 C6 S1 -174.6(2) . . . . ?
C10 C11 C6 C7 3.4(4) . . . . ?
C8 C7 C6 S1 175.2(2) . . . . ?
C8 C7 C6 C11 -2.8(4) . . . . ?
C8 C9 C10 C11 -2.5(4) . . . . ?
C6 S1 C4 C5 179.6(2) . . . . ?
C6 S1 C4 C3 -76.5(3) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C13 C18 C17 C16 0.1(6) . . . . ?
C13 C14 C15 C16 1.2(6) . . . . ?
C12 O4 C9 C10 -174.8(3) . . . . ?
C12 O4 C9 C8 5.0(4) . . . . ?
C12 C13 C18 C17 177.0(3) . . . . ?
C12 C13 C14 C15 -177.6(3) . . . . ?
C18 C13 C12 O4 137.4(3) . . . . ?
C18 C13 C14 C15 -1.4(5) . . . . ?
C4 S1 C6 C7 69.8(3) . . . . ?
C4 S1 C6 C11 -112.2(3) . . . . ?
C4 C5 C2 O1 -141.7(9) . . . . ?
C4 C5 C2 C3 -21.9(3) . . . . ?
C4 C5 C2 O1A -141(2) . . . . ?
C5 C4 C3 C2 -21.7(3) . . . . ?
C5 C2 C3 C4 22.0(3) . . . . ?
C5 C2 O1A C1A -137(4) . . . . ?
C2 O1 C1 F1 -177.8(12) . . . . ?
C2 O1 C1 F3 58.8(19) . . . . ?
C2 O1 C1 F2 -62.8(18) . . . . ?
C14 C13 C12 O4 -46.4(4) . . . . ?
C14 C13 C18 C17 0.7(5) . . . . ?
C14 C15 C16 C17 -0.3(6) . . . . ?
C3 C4 C5 C2 21.7(3) . . . . ?
C3 C2 O1A C1A 122(4) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C1 O1 C2 C5 -156.4(13) . . . . ?
C1 O1 C2 C3 100.2(15) . . . . ?
F1A C1A O1A C2 177(3) . . . . ?
F3A C1A O1A C2 77(5) . . . . ?
F2A C1A O1A C2 -38(7) . . . . ?
O1A C2 C3 C4 135.3(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_yk32_acmi_b
_database_code_depnum_ccdc_archive 'CCDC 2388019'
loop_
_audit_author_name
_audit_author_address
'Yannick Kraemer'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2024-09-30 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-09-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 F5 O4 S2'
_chemical_formula_sum            'C17 H17 F5 O4 S2'
_chemical_formula_weight         444.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   19.244(2)
_cell_length_b                   8.8045(10)
_cell_length_c                   11.2480(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.108(3)
_cell_angle_gamma                90
_cell_volume                     1856.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.8411
_exptl_absorpt_correction_type   'Empirical, SADABS (multi-scan)'
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1035 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.9063.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 1.00 2.00 0.1000
4.00 -1.00 1.00 0.0890
3.00 -2.00 -1.00 0.0970
-4.00 1.00 -1.00 0.1120
-3.00 3.00 2.00 0.1070
3.00 -1.00 -2.00 0.1290
1.00 -4.00 -1.00 0.1310
-2.00 -1.00 1.00 0.1070
4.00 3.00 -2.00 0.0600
4.00 0.00 -1.00 0.0750
1.00 0.00 0.00 0.0640
-1.00 0.00 0.00 0.1090
-4.00 -3.00 -2.00 0.1700
-3.00 4.00 1.00 0.0970
-5.00 -2.00 1.00 0.1160
-5.00 -1.00 1.00 0.1200
-3.00 0.00 4.00 0.1210
0.00 -1.00 1.00 0.1210

_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.214
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            40786
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.067
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  Mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4666
_reflns_number_total             5435
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5435
_refine_ls_number_restraints     283
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.066
_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)+(0.0799P)²+0.7058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1447
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 S2A-F6A \\sim S2A-F3A \\sim S2A-F4A \\sim S2A-F2A \\sim S2-F1 \\sim S2-F4
\\sim S2-F3 \\sim S2A-F1A \\sim S2-
 F6 \\sim S2-F2
 with sigma of 0.02
 S2-O3 \\sim S2A-O3A
 with sigma of 0.02
 O3A-C1 \\sim O3-C1
 with sigma of 0.02
3. Restrained angles
 F1-F3-F4
 fixed at 90 with sigma of 0.02
 F3-S2-F1
 fixed at 90 with sigma of 0.02
 F3-S2-F4
 fixed at 90 with sigma of 0.02
 F4-S2-F2
 fixed at 90 with sigma of 0.02
 F2-S2-F1
 fixed at 90 with sigma of 0.02
 F1-S2-F4
 fixed at 180 with sigma of 0.02
 F2-S2-F3
 fixed at 180 with sigma of 0.02
 O3-S2-F6
 fixed at 180 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C1 \\sim O3A \\sim O3 \\sim F3 \\sim F4 \\sim F1A \\sim F6 \\sim F1 \\sim F2A
\\sim F2 \\sim F6A \\sim F4A \\sim F3A: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C1, O3, O3A, F3, F4, F1A, F6, F2A, F6A, F1, F2, F4A, F3A, S2A, S2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(S2A)=Sof(O3A)=Sof(F2A)=Sof(F6A)=Sof(F4A)=Sof(F1A)=Sof(F3A)=1-FVAR(1)
 Sof(S2)=Sof(O3)=Sof(F2)=Sof(F6)=Sof(F4)=Sof(F1)=Sof(F3)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C4(H4)
7.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C2(H2A,H2B), C3(H3A,H3B)
7.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C9(H9), C7(H7), C17(H17), C13(H13), C15(H15), C14(H14),
 C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.64670(2) 0.64070(4) 0.30423(3) 0.03190(11) Uani 1 1 d . . . . .
S2 S 0.94873(8) 0.67179(19) 0.6149(2) 0.0810(6) Uani 0.660(3) 1 d D . P A 1
O5 O 0.37712(6) 0.69951(11) 0.46328(10) 0.0303(2) Uani 1 1 d . . . . .
O1 O 0.66636(7) 0.79303(14) 0.27900(13) 0.0455(3) Uani 1 1 d . . . . .
O4 O 0.63487(7) 0.53148(18) 0.20622(13) 0.0518(3) Uani 1 1 d . . . . .
C5 C 0.56899(8) 0.65026(14) 0.36104(13) 0.0283(3) Uani 1 1 d . . . . .
C8 C 0.44223(7) 0.68639(14) 0.43617(12) 0.0262(2) Uani 1 1 d . . . . .
C10 C 0.56329(8) 0.76281(15) 0.44550(13) 0.0304(3) Uani 1 1 d . . . . .
H10 H 0.602738 0.827479 0.476600 0.037 Uiso 1 1 calc R U . . .
C6 C 0.51229(8) 0.55101(15) 0.31833(12) 0.0291(3) Uani 1 1 d . . . . .
H6 H 0.517071 0.471344 0.263785 0.035 Uiso 1 1 calc R U . . .
C9 C 0.50043(8) 0.78088(14) 0.48431(13) 0.0295(3) Uani 1 1 d . . . . .
H9 H 0.496806 0.856455 0.542889 0.035 Uiso 1 1 calc R U . . .
C7 C 0.44914(7) 0.56905(15) 0.35571(12) 0.0286(3) Uani 1 1 d . . . . .
H7 H 0.410410 0.501768 0.326756 0.034 Uiso 1 1 calc R U . . .
C12 C 0.28790(8) 0.84281(16) 0.53183(15) 0.0329(3) Uani 1 1 d . . . . .
C4 C 0.71377(8) 0.56861(17) 0.42444(15) 0.0360(3) Uani 1 1 d . . . . .
H4 H 0.699459 0.467207 0.451060 0.043 Uiso 1 1 calc R U . . .
C11 C 0.36608(8) 0.82726(17) 0.53735(14) 0.0337(3) Uani 1 1 d . . . . .
H11A H 0.384264 0.921206 0.506724 0.040 Uiso 1 1 calc R U . . .
H11B H 0.392352 0.811253 0.622864 0.040 Uiso 1 1 calc R U . . .
C2 C 0.78960(9) 0.5613(2) 0.40179(19) 0.0473(4) Uani 1 1 d . . . . .
H2A H 0.803988 0.459189 0.379290 0.057 Uiso 1 1 calc R U . . .
H2B H 0.799895 0.640177 0.345487 0.057 Uiso 1 1 calc R U . . .
C17 C 0.26304(11) 0.8518(2) 0.63785(17) 0.0453(4) Uani 1 1 d . . . . .
H17 H 0.295590 0.844341 0.714954 0.054 Uiso 1 1 calc R U . . .
C13 C 0.23980(11) 0.8548(2) 0.42010(18) 0.0490(4) Uani 1 1 d . . . . .
H13 H 0.256282 0.849924 0.346718 0.059 Uiso 1 1 calc R U . . .
O3 O 0.86718(18) 0.7167(4) 0.5778(4) 0.0714(11) Uani 0.660(3) 1 d D U P A 1
C15 C 0.14306(11) 0.8829(2) 0.5212(2) 0.0541(5) Uani 1 1 d . . . . .
H15 H 0.093653 0.896683 0.517516 0.065 Uiso 1 1 calc R U . . .
C14 C 0.16753(12) 0.8739(3) 0.4151(2) 0.0607(6) Uani 1 1 d . . . . .
H14 H 0.134736 0.880805 0.338195 0.073 Uiso 1 1 calc R U . . .
C1 C 0.81529(11) 0.5999(3) 0.5357(2) 0.0522(5) Uani 1 1 d D U . . .
C16 C 0.19064(12) 0.8719(3) 0.6321(2) 0.0552(5) Uani 1 1 d . . . . .
H16 H 0.174017 0.877895 0.705263 0.066 Uiso 1 1 calc R U . . .
C3 C 0.74346(13) 0.6693(3) 0.53586(19) 0.0621(6) Uani 1 1 d . . . . .
H3A H 0.740350 0.779651 0.518495 0.075 Uiso 1 1 calc R U . . .
H3B H 0.725007 0.644285 0.608811 0.075 Uiso 1 1 calc R U . . .
F2 F 0.9391(3) 0.5825(7) 0.7303(4) 0.1260(17) Uani 0.660(3) 1 d D U P A 1
F6 F 1.03100(18) 0.6357(5) 0.6523(5) 0.135(2) Uani 0.660(3) 1 d D U P A 1
F4 F 0.93872(13) 0.5245(4) 0.5420(4) 0.1199(14) Uani 0.660(3) 1 d D U P A 1
F1 F 0.9640(3) 0.8194(6) 0.6821(9) 0.212(4) Uani 0.660(3) 1 d D U P A 1
F3 F 0.9641(2) 0.7629(8) 0.5093(6) 0.211(3) Uani 0.660(3) 1 d D U P A 1
S2A S 0.93869(11) 0.6927(3) 0.6723(3) 0.0519(5) Uani 0.340(3) 1 d D . P A 2
O3A O 0.8857(3) 0.6786(7) 0.5427(5) 0.0523(13) Uani 0.340(3) 1 d D U P A 2
F2A F 0.9280(6) 0.8605(8) 0.6872(11) 0.139(4) Uani 0.340(3) 1 d D U P A 2
F6A F 0.9934(3) 0.7072(8) 0.7962(6) 0.108(2) Uani 0.340(3) 1 d D U P A 2
F4A F 0.8783(3) 0.6735(10) 0.7436(5) 0.113(2) Uani 0.340(3) 1 d D U P A 2
F1A F 1.0023(4) 0.6973(16) 0.6138(8) 0.144(4) Uani 0.340(3) 1 d D U P A 2
F3A F 0.9473(4) 0.5160(6) 0.6779(8) 0.092(2) Uani 0.340(3) 1 d D U P A 2
H1 H 0.8254(14) 0.509(3) 0.593(2) 0.063(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4392(12) . ?
S1 O4 1.4416(13) . ?
S1 C5 1.7564(15) . ?
S1 C4 1.7622(15) . ?
S2 O3 1.580(4) . ?
S2 F2 1.564(5) . ?
S2 F6 1.575(4) . ?
S2 F4 1.523(4) . ?
S2 F1 1.499(5) . ?
S2 F3 1.517(5) . ?
O5 C8 1.3600(17) . ?
O5 C11 1.4438(17) . ?
C5 C10 1.3941(19) . ?
C5 C6 1.3954(19) . ?
C8 C9 1.4017(19) . ?
C8 C7 1.3995(18) . ?
C10 H10 0.9500 . ?
C10 C9 1.385(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(2) . ?
C9 H9 0.9500 . ?
C7 H7 0.9500 . ?
C12 C11 1.498(2) . ?
C12 C17 1.384(2) . ?
C12 C13 1.385(2) . ?
C4 H4 1.0000 . ?
C4 C2 1.539(2) . ?
C4 C3 1.536(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.514(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.391(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(3) . ?
O3 C1 1.437(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.381(3) . ?
C15 C16 1.373(3) . ?
C14 H14 0.9500 . ?
C1 C3 1.512(3) . ?
C1 O3A 1.509(5) . ?
C1 H1 1.01(3) . ?
C16 H16 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
S2A O3A 1.583(6) . ?
S2A F2A 1.506(7) . ?
S2A F6A 1.549(5) . ?
S2A F4A 1.564(6) . ?
S2A F1A 1.517(7) . ?
S2A F3A 1.564(6) . ?

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
O1 S1 O4 118.28(9) . . ?
O1 S1 C5 108.11(7) . . ?
O1 S1 C4 107.90(8) . . ?
O4 S1 C5 108.08(7) . . ?
O4 S1 C4 107.91(8) . . ?
C5 S1 C4 105.90(7) . . ?
F2 S2 O3 92.7(3) . . ?
F2 S2 F6 88.7(3) . . ?
F6 S2 O3 177.1(2) . . ?
F4 S2 O3 94.25(17) . . ?
F4 S2 F2 89.7(3) . . ?
F4 S2 F6 88.2(2) . . ?
F1 S2 O3 89.1(3) . . ?
F1 S2 F2 93.6(5) . . ?
F1 S2 F6 88.3(3) . . ?
F1 S2 F4 175.1(4) . . ?
F1 S2 F3 83.4(5) . . ?
F3 S2 O3 91.1(2) . . ?
F3 S2 F2 175.1(3) . . ?
F3 S2 F6 87.3(3) . . ?
F3 S2 F4 93.0(4) . . ?
C8 O5 C11 117.34(11) . . ?
C10 C5 S1 119.14(11) . . ?
C10 C5 C6 120.23(14) . . ?
C6 C5 S1 120.57(11) . . ?
O5 C8 C9 123.99(12) . . ?
O5 C8 C7 115.81(12) . . ?
C7 C8 C9 120.20(13) . . ?
C5 C10 H10 119.8 . . ?
C9 C10 C5 120.38(13) . . ?
C9 C10 H10 119.8 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.74(13) . . ?
C7 C6 H6 120.1 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.24(12) . . ?
C10 C9 H9 120.4 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.05(12) . . ?
C6 C7 H7 120.0 . . ?
C17 C12 C11 120.64(15) . . ?
C17 C12 C13 119.13(16) . . ?
C13 C12 C11 120.18(15) . . ?
S1 C4 H4 110.4 . . ?
C2 C4 S1 116.44(12) . . ?
C2 C4 H4 110.4 . . ?
C3 C4 S1 119.37(13) . . ?
C3 C4 H4 110.4 . . ?
C3 C4 C2 88.17(14) . . ?
O5 C11 C12 108.98(12) . . ?
O5 C11 H11A 109.9 . . ?
O5 C11 H11B 109.9 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C4 C2 H2A 114.3 . . ?
C4 C2 H2B 114.3 . . ?
H2A C2 H2B 111.4 . . ?
C1 C2 C4 86.20(15) . . ?
C1 C2 H2A 114.3 . . ?
C1 C2 H2B 114.3 . . ?
C12 C17 H17 119.8 . . ?
C12 C17 C16 120.34(18) . . ?
C16 C17 H17 119.8 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.18(18) . . ?
C14 C13 H13 119.9 . . ?
C1 O3 S2 118.8(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C16 C15 C14 119.54(19) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C2 C1 H1 115.1(15) . . ?
O3 C1 C2 122.3(3) . . ?
O3 C1 C3 106.1(2) . . ?
O3 C1 H1 109.5(15) . . ?
C3 C1 C2 89.98(14) . . ?
C3 C1 H1 111.3(15) . . ?
O3A C1 C2 104.0(3) . . ?
O3A C1 C3 128.7(3) . . ?
O3A C1 H1 106.6(15) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 C17 120.40(19) . . ?
C15 C16 H16 119.8 . . ?
C4 C3 H3A 114.3 . . ?
C4 C3 H3B 114.3 . . ?
C1 C3 C4 86.37(16) . . ?
C1 C3 H3A 114.3 . . ?
C1 C3 H3B 114.3 . . ?
H3A C3 H3B 111.4 . . ?
F2A S2A O3A 95.9(5) . . ?
F2A S2A F6A 84.3(5) . . ?
F2A S2A F4A 85.0(6) . . ?
F2A S2A F1A 99.5(7) . . ?
F2A S2A F3A 170.8(7) . . ?
F6A S2A O3A 177.4(4) . . ?
F6A S2A F4A 88.9(4) . . ?
F6A S2A F3A 90.1(4) . . ?
F4A S2A O3A 93.7(3) . . ?
F4A S2A F3A 87.5(5) . . ?
F1A S2A O3A 91.0(4) . . ?
F1A S2A F6A 86.4(4) . . ?
F1A S2A F4A 173.1(6) . . ?
F1A S2A F3A 87.4(6) . . ?
F3A S2A O3A 90.0(4) . . ?
C1 O3A S2A 117.9(4) . . ?

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 C5 C10 C9 174.73(11) . . . . ?
S1 C5 C6 C7 -174.12(10) . . . . ?
S1 C4 C2 C1 144.70(13) . . . . ?
S1 C4 C3 C1 -142.13(14) . . . . ?
S2 O3 C1 C2 -92.3(4) . . . . ?
S2 O3 C1 C3 167.2(3) . . . . ?
O5 C8 C9 C10 -176.55(12) . . . . ?
O5 C8 C7 C6 177.05(12) . . . . ?
O1 S1 C5 C10 -42.25(13) . . . . ?
O1 S1 C5 C6 134.90(12) . . . . ?
O1 S1 C4 C2 -59.53(15) . . . . ?
O1 S1 C4 C3 44.29(17) . . . . ?
O4 S1 C5 C10 -171.39(12) . . . . ?
O4 S1 C5 C6 5.77(14) . . . . ?
O4 S1 C4 C2 69.35(14) . . . . ?
O4 S1 C4 C3 173.17(16) . . . . ?
C5 S1 C4 C2 -175.10(12) . . . . ?
C5 S1 C4 C3 -71.28(16) . . . . ?
C5 C10 C9 C8 -1.1(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C8 O5 C11 C12 166.52(12) . . . . ?
C10 C5 C6 C7 3.0(2) . . . . ?
C6 C5 C10 C9 -2.4(2) . . . . ?
C9 C8 C7 C6 -3.4(2) . . . . ?
C7 C8 C9 C10 4.0(2) . . . . ?
C12 C17 C16 C15 0.0(3) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C4 S1 C5 C10 73.18(12) . . . . ?
C4 S1 C5 C6 -109.67(12) . . . . ?
C4 C2 C1 O3 -132.1(2) . . . . ?
C4 C2 C1 C3 -22.92(16) . . . . ?
C4 C2 C1 O3A -153.0(3) . . . . ?
C11 O5 C8 C9 5.83(19) . . . . ?
C11 O5 C8 C7 -174.69(12) . . . . ?
C11 C12 C17 C16 177.65(17) . . . . ?
C11 C12 C13 C14 -178.02(19) . . . . ?
C2 C4 C3 C1 -22.58(16) . . . . ?
C2 C1 C3 C4 22.96(16) . . . . ?
C2 C1 O3A S2A -162.4(4) . . . . ?
C17 C12 C11 O5 128.01(15) . . . . ?
C17 C12 C13 C14 -0.7(3) . . . . ?
C13 C12 C11 O5 -54.73(19) . . . . ?
C13 C12 C17 C16 0.4(3) . . . . ?
O3 C1 C3 C4 146.8(2) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C16 C15 C14 C13 -0.4(4) . . . . ?
C3 C4 C2 C1 22.55(16) . . . . ?
C3 C1 O3A S2A 96.1(5) . . . . ?
F2 S2 O3 C1 -69.0(5) . . . . ?
F4 S2 O3 C1 20.9(4) . . . . ?
F1 S2 O3 C1 -162.6(6) . . . . ?
F3 S2 O3 C1 114.0(5) . . . . ?
O3A C1 C3 C4 131.0(3) . . . . ?
F2A S2A O3A C1 -107.5(7) . . . . ?
F4A S2A O3A C1 -22.1(6) . . . . ?
F1A S2A O3A C1 152.8(7) . . . . ?
F3A S2A O3A C1 65.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_acmi_yk28_81_a
_database_code_depnum_ccdc_archive 'CCDC 2388015'
loop_
_audit_author_name
_audit_author_address
'Yannick Kraemer'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2024-09-30 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-08-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 F7 O3 S2'
_chemical_formula_sum            'C18 H17 F7 O3 S2'
_chemical_formula_weight         478.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   17.3628(4)
_cell_length_b                   5.49420(10)
_cell_length_c                   21.4770(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.7710(10)
_cell_angle_gamma                90
_cell_volume                     1939.82(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9778
_cell_measurement_temperature    133.00
_cell_measurement_theta_max      72.10
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.896
_shelx_estimated_absorpt_T_min   0.507
_exptl_absorpt_coefficient_mu    3.293
_exptl_absorpt_correction_T_max  0.7303
_exptl_absorpt_correction_T_min  0.6147
_exptl_absorpt_correction_type   'Empirical, SADABS (multi-scan)'
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0819 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.8417.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             976
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.0620
0.00 1.00 0.00 0.1190
-1.00 0.00 -1.00 0.0390
1.00 0.00 1.00 0.0050
-1.00 0.00 1.00 0.0130
1.00 0.00 -1.00 0.0170

_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40894
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.132
_diffrn_reflns_theta_min         2.861
_diffrn_ambient_temperature      133.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  Mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3386
_reflns_number_total             3825
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.120
_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)+(0.0582P)²+1.5250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1096
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F1A-C1 \\sim F2-C1 \\sim F2A-C1 \\sim F3-C1 \\sim F3A-C1 \\sim F1-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
S1 \\sim C1 \\sim F2 \\sim F3 \\sim F1 \\sim F2A \\sim F1A \\sim F3A: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
4. Rigid body (RIGU) restrains
 C1, F2, F3, F1, F2A, F1A, F3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F2A)=Sof(F1A)=Sof(F3A)=1-FVAR(1)
 Sof(F2)=Sof(F3)=Sof(F1)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C12(H12A,H12B)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C18(H18), C14(H14), C16(H16), C17(H17), C15(H15), C8(H8),
 C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S2 S 0.35056(3) 0.25693(9) 0.71488(2) 0.03057(14) Uani 1 1 d . . . . .
S1 S 0.56777(3) 0.31607(9) 0.92633(2) 0.03194(15) Uani 1 1 d . U . . .
F4 F 0.51232(9) 0.1853(3) 0.96308(7) 0.0510(4) Uani 1 1 d . . . . .
F7 F 0.58889(10) 0.5245(3) 0.98152(7) 0.0585(4) Uani 1 1 d . . . . .
F5 F 0.55188(8) 0.0919(2) 0.87544(7) 0.0410(3) Uani 1 1 d . . . . .
F6 F 0.62934(8) 0.4405(3) 0.89263(7) 0.0469(4) Uani 1 1 d . . . . .
O1 O 0.40046(11) 0.0414(3) 0.73039(8) 0.0409(4) Uani 1 1 d . . . . .
O3 O 0.39854(9) 0.7121(3) 0.48233(7) 0.0316(3) Uani 1 1 d . . . . .
O2 O 0.26415(10) 0.2313(3) 0.70079(9) 0.0470(4) Uani 1 1 d . . . . .
C7 C 0.42541(12) 0.3115(4) 0.62103(10) 0.0287(4) Uani 1 1 d . . . . .
H7 H 0.457619 0.174352 0.640286 0.034 Uiso 1 1 calc R U . . .
C11 C 0.32353(12) 0.6104(4) 0.62200(10) 0.0297(4) Uani 1 1 d . . . . .
H11 H 0.286123 0.674950 0.641666 0.036 Uiso 1 1 calc R U . . .
C3 C 0.39796(12) 0.3579(4) 0.84935(10) 0.0319(4) Uani 1 1 d . . . . .
H3A H 0.358949 0.421092 0.870376 0.038 Uiso 1 1 calc R U . . .
H3B H 0.400549 0.177873 0.851049 0.038 Uiso 1 1 calc R U . . .
C2 C 0.48174(12) 0.4836(4) 0.87247(10) 0.0296(4) Uani 1 1 d . . . . .
H2 H 0.477053 0.644500 0.892741 0.036 Uiso 1 1 calc R U . . .
C4 C 0.38694(12) 0.4666(4) 0.78016(10) 0.0273(4) Uani 1 1 d . . . . .
H4 H 0.353747 0.619109 0.772226 0.033 Uiso 1 1 calc R U . . .
C18 C 0.40079(13) 1.1362(4) 0.37235(11) 0.0338(5) Uani 1 1 d . . . . .
H18 H 0.422626 1.249274 0.407020 0.041 Uiso 1 1 calc R U . . .
C1 C 0.65975(15) 0.1434(5) 0.98046(13) 0.0454(5) Uani 1 1 d D U . . .
C14 C 0.32528(14) 0.7749(4) 0.33100(11) 0.0370(5) Uani 1 1 d . . . . .
H14 H 0.295162 0.638033 0.337241 0.044 Uiso 1 1 calc R U . . .
C5 C 0.47890(12) 0.5214(4) 0.80065(10) 0.0291(4) Uani 1 1 d . . . . .
H5A H 0.510528 0.399934 0.784937 0.035 Uiso 1 1 calc R U . . .
H5B H 0.491946 0.689249 0.790591 0.035 Uiso 1 1 calc R U . . .
C12 C 0.34338(13) 0.9001(4) 0.44710(10) 0.0311(4) Uani 1 1 d . . . . .
H12A H 0.353877 1.053264 0.472730 0.037 Uiso 1 1 calc R U . . .
H12B H 0.286392 0.850277 0.440029 0.037 Uiso 1 1 calc R U . . .
C9 C 0.38744(11) 0.6236(4) 0.53817(9) 0.0270(4) Uani 1 1 d . . . . .
C16 C 0.38092(14) 1.0093(4) 0.26140(11) 0.0384(5) Uani 1 1 d . . . . .
H16 H 0.388971 1.034250 0.220157 0.046 Uiso 1 1 calc R U . . .
C6 C 0.36845(11) 0.4040(4) 0.64811(9) 0.0264(4) Uani 1 1 d . . . . .
C17 C 0.41303(15) 1.1716(4) 0.31206(12) 0.0398(5) Uani 1 1 d . . . . .
H17 H 0.443504 1.307714 0.305826 0.048 Uiso 1 1 calc R U . . .
C13 C 0.35705(12) 0.9374(4) 0.38225(10) 0.0287(4) Uani 1 1 d . . . . .
C15 C 0.33701(15) 0.8101(5) 0.27047(11) 0.0417(5) Uani 1 1 d . . . . .
H15 H 0.314970 0.697968 0.235613 0.050 Uiso 1 1 calc R U . . .
C8 C 0.43454(12) 0.4208(4) 0.56607(10) 0.0291(4) Uani 1 1 d . . . . .
H8 H 0.472922 0.358241 0.547116 0.035 Uiso 1 1 calc R U . . .
C10 C 0.33336(12) 0.7224(4) 0.56710(10) 0.0292(4) Uani 1 1 d . . . . .
H10 H 0.303450 0.865208 0.549430 0.035 Uiso 1 1 calc R U . . .
F2 F 0.6840(2) -0.0220(8) 0.94638(15) 0.0761(13) Uani 0.703(7) 1 d D U P A 1
F3 F 0.7193(3) 0.2826(10) 1.0083(3) 0.0626(11) Uani 0.703(7) 1 d D U P A 1
F1 F 0.64084(16) 0.0178(7) 1.0279(2) 0.0608(9) Uani 0.703(7) 1 d D U P A 1
F2A F 0.7111(4) 0.1190(18) 0.9435(4) 0.0713(18) Uani 0.297(7) 1 d D U P A 2
F1A F 0.6438(4) -0.0550(12) 0.9933(5) 0.063(2) Uani 0.297(7) 1 d D U P A 2
F3A F 0.7033(8) 0.290(3) 1.0270(6) 0.074(3) Uani 0.297(7) 1 d D U P A 2


_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
S2 O1 1.4415(16) . ?
S2 O2 1.4387(16) . ?
S2 C4 1.767(2) . ?
S2 C6 1.759(2) . ?
S1 F4 1.5985(15) . ?
S1 F7 1.6033(15) . ?
S1 F5 1.6105(14) . ?
S1 F6 1.6222(14) . ?
S1 C2 1.818(2) . ?
S1 C1 1.899(2) . ?
O3 C12 1.446(2) . ?
O3 C9 1.364(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.395(3) . ?
C7 C8 1.378(3) . ?
C11 H11 0.9500 . ?
C11 C6 1.388(3) . ?
C11 C10 1.388(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.541(3) . ?
C3 C4 1.555(3) . ?
C2 H2 1.0000 . ?
C2 C5 1.541(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.543(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.392(3) . ?
C18 C13 1.385(3) . ?
C1 F2 1.318(4) . ?
C1 F3 1.271(5) . ?
C1 F1 1.356(4) . ?
C1 F2A 1.379(7) . ?
C1 F1A 1.179(6) . ?
C1 F3A 1.315(10) . ?
C14 H14 0.9500 . ?
C14 C13 1.386(3) . ?
C14 C15 1.392(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.501(3) . ?
C9 C8 1.398(3) . ?
C9 C10 1.392(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(3) . ?
C16 C15 1.383(3) . ?
C17 H17 0.9500 . ?
C15 H15 0.9500 . ?
C8 H8 0.9500 . ?
C10 H10 0.9500 . ?

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
O1 S2 C4 108.50(10) . . ?
O1 S2 C6 108.36(10) . . ?
O2 S2 O1 118.48(11) . . ?
O2 S2 C4 108.24(10) . . ?
O2 S2 C6 108.62(10) . . ?
C6 S2 C4 103.63(9) . . ?
F4 S1 F7 89.23(10) . . ?
F4 S1 F5 89.58(9) . . ?
F4 S1 F6 176.15(8) . . ?
F4 S1 C2 92.27(8) . . ?
F4 S1 C1 89.70(10) . . ?
F7 S1 F5 175.11(8) . . ?
F7 S1 F6 90.13(9) . . ?
F7 S1 C2 93.11(9) . . ?
F7 S1 C1 87.53(10) . . ?
F5 S1 F6 90.75(8) . . ?
F5 S1 C2 91.67(8) . . ?
F5 S1 C1 87.72(9) . . ?
F6 S1 C2 91.56(8) . . ?
F6 S1 C1 86.48(10) . . ?
C2 S1 C1 177.94(11) . . ?
C9 O3 C12 117.22(15) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C8 C7 C6 119.39(18) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C6 119.89(18) . . ?
H3A C3 H3B 111.3 . . ?
C2 C3 H3A 114.1 . . ?
C2 C3 H3B 114.1 . . ?
C2 C3 C4 87.06(15) . . ?
C4 C3 H3A 114.1 . . ?
C4 C3 H3B 114.1 . . ?
S1 C2 H2 109.6 . . ?
C3 C2 S1 118.36(15) . . ?
C3 C2 H2 109.6 . . ?
C3 C2 C5 90.86(15) . . ?
C5 C2 S1 117.39(14) . . ?
C5 C2 H2 109.6 . . ?
S2 C4 H4 111.8 . . ?
C3 C4 S2 114.23(14) . . ?
C3 C4 H4 111.8 . . ?
C5 C4 S2 115.23(14) . . ?
C5 C4 C3 90.26(15) . . ?
C5 C4 H4 111.8 . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C13 C18 C17 120.6(2) . . ?
F2 C1 S1 111.15(19) . . ?
F2 C1 F1 105.4(3) . . ?
F3 C1 S1 112.6(3) . . ?
F3 C1 F2 108.6(3) . . ?
F3 C1 F1 108.0(3) . . ?
F1 C1 S1 110.8(2) . . ?
F2A C1 S1 105.6(3) . . ?
F1A C1 S1 113.0(4) . . ?
F1A C1 F2A 106.8(6) . . ?
F1A C1 F3A 120.6(8) . . ?
F3A C1 S1 109.0(7) . . ?
F3A C1 F2A 100.2(7) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C2 C5 C4 87.49(14) . . ?
C2 C5 H5A 114.1 . . ?
C2 C5 H5B 114.1 . . ?
C4 C5 H5A 114.1 . . ?
C4 C5 H5B 114.1 . . ?
H5A C5 H5B 111.3 . . ?
O3 C12 H12A 110.1 . . ?
O3 C12 H12B 110.1 . . ?
O3 C12 C13 107.89(16) . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
O3 C9 C8 115.61(17) . . ?
O3 C9 C10 124.04(18) . . ?
C10 C9 C8 120.34(18) . . ?
C17 C16 H16 119.9 . . ?
C17 C16 C15 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C7 C6 S2 120.51(15) . . ?
C11 C6 S2 118.75(15) . . ?
C11 C6 C7 120.73(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C13 C14 118.92(19) . . ?
C18 C13 C12 120.56(19) . . ?
C14 C13 C12 120.52(19) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C7 C8 C9 120.12(18) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C11 C10 C9 119.42(18) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?

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
S2 C4 C5 C2 -132.74(14) . . . . ?
S1 C2 C5 C4 138.63(15) . . . . ?
F4 S1 C2 C3 -35.34(17) . . . . ?
F4 S1 C2 C5 -142.73(16) . . . . ?
F4 S1 C1 F2 109.9(3) . . . . ?
F4 S1 C1 F3 -128.0(3) . . . . ?
F4 S1 C1 F1 -6.9(3) . . . . ?
F4 S1 C1 F2A 151.5(5) . . . . ?
F4 S1 C1 F1A 35.1(7) . . . . ?
F4 S1 C1 F3A -101.7(7) . . . . ?
F7 S1 C2 C3 -124.69(16) . . . . ?
F7 S1 C2 C5 127.92(17) . . . . ?
F7 S1 C1 F2 -160.9(3) . . . . ?
F7 S1 C1 F3 -38.7(3) . . . . ?
F7 S1 C1 F1 82.3(3) . . . . ?
F7 S1 C1 F2A -119.3(5) . . . . ?
F7 S1 C1 F1A 124.4(7) . . . . ?
F7 S1 C1 F3A -12.5(7) . . . . ?
F5 S1 C2 C3 54.30(16) . . . . ?
F5 S1 C2 C5 -53.09(16) . . . . ?
F5 S1 C1 F2 20.3(3) . . . . ?
F5 S1 C1 F3 142.4(3) . . . . ?
F5 S1 C1 F1 -96.5(3) . . . . ?
F5 S1 C1 F2A 61.9(5) . . . . ?
F5 S1 C1 F1A -54.5(7) . . . . ?
F5 S1 C1 F3A 168.7(7) . . . . ?
F6 S1 C2 C3 145.10(16) . . . . ?
F6 S1 C2 C5 37.71(16) . . . . ?
F6 S1 C1 F2 -70.6(3) . . . . ?
F6 S1 C1 F3 51.5(3) . . . . ?
F6 S1 C1 F1 172.6(3) . . . . ?
F6 S1 C1 F2A -29.0(5) . . . . ?
F6 S1 C1 F1A -145.4(7) . . . . ?
F6 S1 C1 F3A 77.8(7) . . . . ?
O1 S2 C4 C3 -50.80(16) . . . . ?
O1 S2 C4 C5 51.77(17) . . . . ?
O1 S2 C6 C7 -2.02(19) . . . . ?
O1 S2 C6 C11 176.54(16) . . . . ?
O3 C12 C13 C18 -103.0(2) . . . . ?
O3 C12 C13 C14 77.8(2) . . . . ?
O3 C9 C8 C7 -177.32(18) . . . . ?
O3 C9 C10 C11 176.57(19) . . . . ?
O2 S2 C4 C3 78.97(16) . . . . ?
O2 S2 C4 C5 -178.46(14) . . . . ?
O2 S2 C6 C7 -131.96(17) . . . . ?
O2 S2 C6 C11 46.60(19) . . . . ?
C3 C2 C5 C4 15.76(15) . . . . ?
C3 C4 C5 C2 -15.62(16) . . . . ?
C2 C3 C4 S2 133.63(14) . . . . ?
C2 C3 C4 C5 15.62(15) . . . . ?
C4 S2 C6 C7 113.10(17) . . . . ?
C4 S2 C6 C11 -68.34(17) . . . . ?
C4 C3 C2 S1 -137.71(15) . . . . ?
C4 C3 C2 C5 -15.64(15) . . . . ?
C12 O3 C9 C8 171.84(18) . . . . ?
C12 O3 C9 C10 -8.0(3) . . . . ?
C9 O3 C12 C13 -170.12(17) . . . . ?
C6 S2 C4 C3 -165.82(14) . . . . ?
C6 S2 C4 C5 -63.25(16) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C6 C11 C10 C9 1.0(3) . . . . ?
C17 C18 C13 C14 -0.3(3) . . . . ?
C17 C18 C13 C12 -179.6(2) . . . . ?
C17 C16 C15 C14 0.1(4) . . . . ?
C13 C18 C17 C16 0.5(3) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C15 C14 C13 C18 0.0(3) . . . . ?
C15 C14 C13 C12 179.3(2) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C8 C7 C6 S2 175.80(15) . . . . ?
C8 C7 C6 C11 -2.7(3) . . . . ?
C8 C9 C10 C11 -3.3(3) . . . . ?
C10 C11 C6 S2 -176.57(16) . . . . ?
C10 C11 C6 C7 2.0(3) . . . . ?
C10 C9 C8 C7 2.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_yk27_acmi_sd_a
_database_code_depnum_ccdc_archive 'CCDC 2388018'
loop_
_audit_author_name
_audit_author_address
'Yannick Kraemer'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2024-09-30 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-08-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 F3 O3 S'
_chemical_formula_sum            'C20 H15 F3 O3 S'
_chemical_formula_weight         392.38
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.04840(10)
_cell_length_b                   8.56770(10)
_cell_length_c                   25.6907(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1771.54(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9207
_cell_measurement_temperature    133.00
_cell_measurement_theta_max      72.07
_cell_measurement_theta_min      3.44
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.631
_exptl_absorpt_coefficient_mu    2.074
_exptl_absorpt_correction_T_max  0.7374
_exptl_absorpt_correction_T_min  0.6621
_exptl_absorpt_correction_type   'Empirical, SADABS (multi-scan)'
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0786 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.8979.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -1.00 0.0410
0.00 1.00 1.00 0.0240
1.00 0.00 0.00 0.0530
-1.00 0.00 0.00 0.1220
0.00 0.00 1.00 0.0040
0.00 0.00 -1.00 0.0150

_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            29384
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.148
_diffrn_reflns_theta_min         3.441
_diffrn_ambient_temperature      133.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  Mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3215
_reflns_number_total             3492
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1294 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(7)
_refine_ls_extinction_coef       0.00070(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3492
_refine_ls_number_restraints     93
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.091
_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)+(0.0220P)²+0.3959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0678
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F1-C1 \\sim F1A-C1
 with sigma of 0.02
 F3-C1 \\sim F3A-C1
 with sigma of 0.02
 F2-C1 \\sim F2A-C1
 with sigma of 0.02
 F1-C1 \\sim F2A-C1 \\sim F2-C1 \\sim F3A-C1 \\sim F3-C1 \\sim F1A-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C2 \\sim C1 \\sim F1 \\sim F2A \\sim F2 \\sim F3A \\sim F3 \\sim F1A: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F3)=Sof(F2)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C3(H3), C10(H10), C9(H9), C6(H6), C4(H4), C7(H7), C19(H19),
 C13(H13), C12(H12), C16(H16), C18(H18), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.19580(7) 0.96791(7) 0.37982(2) 0.03867(16) Uani 1 1 d . . . . .
O3 O 0.2095(2) 0.4510(2) 0.53002(6) 0.0433(4) Uani 1 1 d . . . . .
O2 O 0.2320(2) 1.1069(2) 0.40924(7) 0.0474(5) Uani 1 1 d . . . . .
F1 F 0.845(4) 1.007(2) 0.2253(10) 0.083(5) Uani 0.44(7) 1 d D U P A 1
O1 O 0.0444(2) 0.9578(3) 0.35033(7) 0.0497(5) Uani 1 1 d . . . . .
F3 F 0.876(3) 0.771(3) 0.2482(10) 0.065(4) Uani 0.44(7) 1 d D U P A 1
F2 F 0.716(4) 0.822(3) 0.1847(7) 0.074(5) Uani 0.44(7) 1 d D U P A 1
C2 C 0.6217(3) 0.8942(3) 0.26781(9) 0.0356(5) Uani 1 1 d . U . . .
C15 C 0.1792(3) 0.1951(3) 0.56405(9) 0.0379(5) Uani 1 1 d . . . . .
C5 C 0.3625(3) 0.9359(3) 0.33594(9) 0.0331(5) Uani 1 1 d . . . . .
C11 C 0.2029(3) 0.5632(3) 0.49284(9) 0.0368(5) Uani 1 1 d . . . . .
C1 C 0.7645(3) 0.8750(3) 0.23117(10) 0.0444(6) Uani 1 1 d D U . . .
C8 C 0.2022(3) 0.8096(3) 0.42325(8) 0.0364(5) Uani 1 1 d . . . . .
C20 C 0.3024(3) 0.2280(3) 0.60013(10) 0.0425(6) Uani 1 1 d . . . . .
H20 H 0.366468 0.320586 0.596725 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4633(3) 0.8488(3) 0.25348(10) 0.0431(6) Uani 1 1 d . . . . .
H3 H 0.444530 0.803618 0.220228 0.052 Uiso 1 1 calc R U . . .
C10 C 0.1342(3) 0.5435(3) 0.44339(9) 0.0404(6) Uani 1 1 d . . . . .
H10 H 0.087742 0.445870 0.433575 0.048 Uiso 1 1 calc R U . . .
C9 C 0.1344(3) 0.6665(3) 0.40899(9) 0.0410(6) Uani 1 1 d . . . . .
H9 H 0.087850 0.653722 0.375271 0.049 Uiso 1 1 calc R U . . .
C14 C 0.1440(3) 0.2994(3) 0.51847(10) 0.0414(6) Uani 1 1 d . . . . .
H14A H 0.197103 0.257113 0.486702 0.050 Uiso 1 1 calc R U . . .
H14B H 0.022753 0.306024 0.512382 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5209(3) 0.9797(3) 0.35072(9) 0.0390(6) Uani 1 1 d . . . . .
H6 H 0.539883 1.024235 0.384059 0.047 Uiso 1 1 calc R U . . .
C4 C 0.3316(3) 0.8693(3) 0.28771(9) 0.0419(6) Uani 1 1 d . . . . .
H4 H 0.222369 0.838365 0.278259 0.050 Uiso 1 1 calc R U . . .
C7 C 0.6512(3) 0.9582(3) 0.31652(9) 0.0399(5) Uani 1 1 d . . . . .
H7 H 0.760709 0.987230 0.326335 0.048 Uiso 1 1 calc R U . . .
C19 C 0.3325(4) 0.1270(4) 0.64113(11) 0.0506(7) Uani 1 1 d . . . . .
H19 H 0.416517 0.150967 0.665856 0.061 Uiso 1 1 calc R U . . .
C13 C 0.2729(3) 0.8285(3) 0.47233(9) 0.0410(6) Uani 1 1 d . . . . .
H13 H 0.320980 0.925620 0.481930 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2727(3) 0.7058(3) 0.50676(9) 0.0411(6) Uani 1 1 d . . . . .
H12 H 0.320638 0.718426 0.540296 0.049 Uiso 1 1 calc R U . . .
C16 C 0.0881(4) 0.0596(4) 0.57004(13) 0.0541(7) Uani 1 1 d . . . . .
H16 H 0.002990 0.035326 0.545728 0.065 Uiso 1 1 calc R U . . .
C18 C 0.2415(4) -0.0080(4) 0.64621(11) 0.0569(8) Uani 1 1 d . . . . .
H18 H 0.263492 -0.077783 0.674110 0.068 Uiso 1 1 calc R U . . .
C17 C 0.1192(4) -0.0414(4) 0.61098(13) 0.0623(8) Uani 1 1 d . . . . .
H17 H 0.055425 -0.134077 0.614598 0.075 Uiso 1 1 calc R U . . .
F1A F 0.8690(19) 0.9960(15) 0.2311(5) 0.056(3) Uani 0.56(7) 1 d D U P A 2
F2A F 0.719(3) 0.863(5) 0.1818(5) 0.078(5) Uani 0.56(7) 1 d D U P A 2
F3A F 0.856(3) 0.752(3) 0.2423(10) 0.081(4) Uani 0.56(7) 1 d D U P A 2


_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 1.4401(19) . ?
S1 O1 1.4374(18) . ?
S1 C5 1.774(2) . ?
S1 C8 1.757(3) . ?
O3 C11 1.356(3) . ?
O3 C14 1.433(3) . ?
F1 C1 1.312(13) . ?
F3 C1 1.335(13) . ?
F2 C1 1.336(14) . ?
C2 C1 1.494(3) . ?
C2 C3 1.383(4) . ?
C2 C7 1.387(3) . ?
C15 C20 1.386(4) . ?
C15 C14 1.500(4) . ?
C15 C16 1.382(4) . ?
C5 C6 1.382(3) . ?
C5 C4 1.387(3) . ?
C11 C10 1.396(3) . ?
C11 C12 1.392(3) . ?
C1 F1A 1.335(9) . ?
C1 F2A 1.322(12) . ?
C1 F3A 1.318(11) . ?
C8 C9 1.391(3) . ?
C8 C13 1.393(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.376(4) . ?
C9 H9 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C7 1.380(3) . ?
C4 H4 0.9500 . ?
C7 H7 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.375(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.374(4) . ?
C12 H12 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.385(4) . ?
C18 H18 0.9500 . ?
C18 C17 1.368(4) . ?
C17 H17 0.9500 . ?

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 C5 107.95(11) . . ?
O2 S1 C8 107.41(10) . . ?
O1 S1 O2 119.86(12) . . ?
O1 S1 C5 107.27(11) . . ?
O1 S1 C8 108.25(13) . . ?
C8 S1 C5 105.20(11) . . ?
C11 O3 C14 118.82(18) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 C7 120.6(2) . . ?
C7 C2 C1 118.7(2) . . ?
C20 C15 C14 122.4(2) . . ?
C16 C15 C20 118.4(3) . . ?
C16 C15 C14 119.2(2) . . ?
C6 C5 S1 118.76(18) . . ?
C6 C5 C4 121.5(2) . . ?
C4 C5 S1 119.73(18) . . ?
O3 C11 C10 124.8(2) . . ?
O3 C11 C12 115.2(2) . . ?
C12 C11 C10 120.0(2) . . ?
F1 C1 F3 106.4(17) . . ?
F1 C1 F2 109.5(15) . . ?
F1 C1 C2 110.9(10) . . ?
F3 C1 F2 105.3(16) . . ?
F3 C1 C2 112.5(12) . . ?
F2 C1 C2 112.0(14) . . ?
F1A C1 C2 113.5(7) . . ?
F2A C1 C2 113.7(11) . . ?
F2A C1 F1A 103.3(14) . . ?
F3A C1 C2 112.4(10) . . ?
F3A C1 F1A 105.7(13) . . ?
F3A C1 F2A 107.5(14) . . ?
C9 C8 S1 120.11(18) . . ?
C9 C8 C13 120.1(2) . . ?
C13 C8 S1 119.80(19) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C11 C10 H10 120.3 . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 H10 120.3 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
O3 C14 C15 107.99(19) . . ?
O3 C14 H14A 110.1 . . ?
O3 C14 H14B 110.1 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C2 C7 H7 120.1 . . ?
C6 C7 C2 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C20 C19 H19 119.9 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.9 . . ?
C8 C13 H13 120.2 . . ?
C12 C13 C8 119.6(2) . . ?
C12 C13 H13 120.2 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 120.9(3) . . ?
C17 C16 H16 119.5 . . ?
C19 C18 H18 120.1 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9 . . ?

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 C5 C6 C7 -178.7(2) . . . . ?
S1 C5 C4 C3 178.5(2) . . . . ?
S1 C8 C9 C10 -177.95(19) . . . . ?
S1 C8 C13 C12 177.90(19) . . . . ?
O3 C11 C10 C9 179.8(2) . . . . ?
O3 C11 C12 C13 -179.8(2) . . . . ?
O2 S1 C5 C6 32.4(2) . . . . ?
O2 S1 C5 C4 -146.9(2) . . . . ?
O2 S1 C8 C9 164.7(2) . . . . ?
O2 S1 C8 C13 -14.3(2) . . . . ?
O1 S1 C5 C6 162.9(2) . . . . ?
O1 S1 C5 C4 -16.5(2) . . . . ?
O1 S1 C8 C9 34.0(2) . . . . ?
O1 S1 C8 C13 -145.0(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C15 C20 C19 C18 0.6(4) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C5 S1 C8 C9 -80.5(2) . . . . ?
C5 S1 C8 C13 100.6(2) . . . . ?
C5 C6 C7 C2 0.5(4) . . . . ?
C11 O3 C14 C15 175.4(2) . . . . ?
C11 C10 C9 C8 0.0(4) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
C1 C2 C7 C6 178.9(2) . . . . ?
C8 S1 C5 C6 -82.0(2) . . . . ?
C8 S1 C5 C4 98.6(2) . . . . ?
C8 C13 C12 C11 0.2(4) . . . . ?
C20 C15 C14 O3 -20.6(3) . . . . ?
C20 C15 C16 C17 -0.2(4) . . . . ?
C20 C19 C18 C17 -0.8(4) . . . . ?
C3 C2 C1 F1 127.0(17) . . . . ?
C3 C2 C1 F3 -113.9(14) . . . . ?
C3 C2 C1 F2 4.4(15) . . . . ?
C3 C2 C1 F1A 139.0(9) . . . . ?
C3 C2 C1 F2A 21.2(19) . . . . ?
C3 C2 C1 F3A -101.1(15) . . . . ?
C3 C2 C7 C6 -1.2(4) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C9 C8 C13 C12 -1.1(4) . . . . ?
C14 O3 C11 C10 0.8(4) . . . . ?
C14 O3 C11 C12 -178.5(2) . . . . ?
C14 C15 C20 C19 -178.9(2) . . . . ?
C14 C15 C16 C17 178.7(3) . . . . ?
C6 C5 C4 C3 -0.9(4) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C7 C2 C1 F1 -53.1(17) . . . . ?
C7 C2 C1 F3 66.0(14) . . . . ?
C7 C2 C1 F2 -175.7(14) . . . . ?
C7 C2 C1 F1A -41.1(9) . . . . ?
C7 C2 C1 F2A -158.8(19) . . . . ?
C7 C2 C1 F3A 78.8(15) . . . . ?
C7 C2 C3 C4 0.9(4) . . . . ?
C19 C18 C17 C16 0.6(5) . . . . ?
C13 C8 C9 C10 1.0(4) . . . . ?
C12 C11 C10 C9 -0.9(4) . . . . ?
C16 C15 C20 C19 0.0(4) . . . . ?
C16 C15 C14 O3 160.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_YK4CMI_A(1)
_database_code_depnum_ccdc_archive 'CCDC 2356231'
loop_
_audit_author_name
_audit_author_address
'Yannick Kraemer'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2024-05-17 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C10 H10 Br F5 O3 S2'
_chemical_formula_sum            'C10 H10 Br F5 O3 S2'
_chemical_formula_weight         417.217
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.38188 2.46625 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
brennan
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
brennan
F 0.01756 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
brennan
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
brennan
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
brennan
S 0.12485 0.12449 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
brennan

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   15.2423(19)
_cell_length_b                   8.1807(10)
_cell_length_c                   12.1223(15)
_cell_angle_alpha                90
_cell_angle_beta                 113.086(2)
_cell_angle_gamma                90
_cell_volume                     1390.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9198
_cell_measurement_temperature    90.15
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.88
_exptl_absorpt_coefficient_mu    3.319
_exptl_absorpt_correction_T_max  0.5629
_exptl_absorpt_correction_T_min  0.4554
_exptl_absorpt_correction_type   'Empirical, SADABS (multi-scan)'
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0847 before and 0.0489 after correction.
The Ratio of minimum to maximum transmission is 0.8090.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.993
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             824.876
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.108
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9981
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12254
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9981
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.88
_diffrn_ambient_temperature      90.15
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -19
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2775
_reflns_number_total             3193
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.5975
_refine_diff_density_min         -0.4400
_refine_diff_density_rms         0.0993
_refine_ls_d_res_high            0.7695
_refine_ls_d_res_low             7.0660
_refine_ls_goodness_of_fit_ref   1.0320
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0248
_refine_ls_restrained_S_all      1.0320
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0196P)²+1.3232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0534
_refine_ls_wR_factor_ref         0.0561
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C3(H3), C6(H6), C2(H2)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br1 Br 0.362386(16) 0.13481(3) 0.700161(18) 0.01920(7) Uani 1.000000 .
S1 S 0.16267(4) 0.26688(6) 0.56017(4) 0.01511(11) Uani 1.000000 .
S2 S 0.37548(4) 0.76177(6) 0.43055(5) 0.01869(12) Uani 1.000000 .
F1 F 0.31627(10) 0.80286(16) 0.50813(12) 0.0239(3) Uani 1.000000 .
F3 F 0.43451(11) 0.73122(17) 0.35163(13) 0.0298(3) Uani 1.000000 .
F4 F 0.27946(10) 0.75157(16) 0.31452(12) 0.0274(3) Uani 1.000000 .
F2 F 0.47064(10) 0.78547(17) 0.54367(12) 0.0285(3) Uani 1.000000 .
F5 F 0.37763(10) 0.95084(16) 0.40446(13) 0.0289(3) Uani 1.000000 .
O2 O 0.11094(11) 0.38387(17) 0.46857(13) 0.0192(3) Uani 1.000000 .
O1 O 0.15713(11) 0.27802(19) 0.67601(13) 0.0207(3) Uani 1.000000 .
O3 O 0.37648(11) 0.57002(18) 0.45396(14) 0.0195(3) Uani 1.000000 .
C5 C 0.09748(15) 0.0471(3) 0.37788(18) 0.0170(4) Uani 1.000000 .
H5 H 0.09551(15) 0.1364(3) 0.32682(18) 0.0203(5) Uiso 1.000000 R
C4 C 0.12919(14) 0.0689(2) 0.50158(18) 0.0142(4) Uani 1.000000 .
C10 C 0.30335(16) 0.3060(3) 0.46508(18) 0.0173(4) Uani 1.000000 .
H10a H 0.36615(16) 0.2642(3) 0.47164(18) 0.0207(5) Uiso 1.000000 R
H10b H 0.25109(16) 0.2602(3) 0.39395(18) 0.0207(5) Uiso 1.000000 R
C1 C 0.07230(16) -0.2377(3) 0.4066(2) 0.0202(5) Uani 1.000000 .
H1 H 0.05274(16) -0.3436(3) 0.3740(2) 0.0243(5) Uiso 1.000000 R
C3 C 0.13236(15) -0.0596(3) 0.57836(19) 0.0175(4) Uani 1.000000 .
H3 H 0.15337(15) -0.0422(3) 0.66229(19) 0.0209(5) Uiso 1.000000 R
C7 C 0.28635(15) 0.2926(3) 0.58274(18) 0.0150(4) Uani 1.000000 .
C9 C 0.29939(16) 0.4922(3) 0.47606(19) 0.0164(4) Uani 1.000000 .
H9 H 0.23549(16) 0.5385(3) 0.42543(19) 0.0197(5) Uiso 1.000000 R
C6 C 0.06885(16) -0.1079(3) 0.33103(19) 0.0191(4) Uani 1.000000 .
H6 H 0.04683(16) -0.1254(3) 0.24700(19) 0.0230(5) Uiso 1.000000 R
C8 C 0.31454(16) 0.4757(3) 0.60915(19) 0.0180(4) Uani 1.000000 .
H8a H 0.26942(16) 0.5407(3) 0.63188(19) 0.0216(5) Uiso 1.000000 R
H8b H 0.38121(16) 0.4933(3) 0.66612(19) 0.0216(5) Uiso 1.000000 R
C2 C 0.10414(16) -0.2137(3) 0.5295(2) 0.0200(5) Uani 1.000000 .
H2 H 0.10662(16) -0.3033(3) 0.5805(2) 0.0241(5) Uiso 1.000000 R


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
Br1 C7 1.934(2) . ?
S1 O2 1.4436(15) . ?
S1 O1 1.4423(15) . ?
S1 C4 1.761(2) . ?
S1 C7 1.808(2) . ?
S2 F1 1.5739(14) . ?
S2 F3 1.5692(14) . ?
S2 F4 1.5852(14) . ?
S2 F2 1.5691(14) . ?
S2 F5 1.5817(14) . ?
S2 O3 1.5931(16) . ?
O3 C9 1.451(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.395(3) . ?
C5 C6 1.389(3) . ?
C4 C3 1.393(3) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C10 C7 1.550(3) . ?
C10 C9 1.532(3) . ?
C1 H1 0.9500 . ?
C1 C6 1.390(3) . ?
C1 C2 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.387(3) . ?
C7 C8 1.557(3) . ?
C9 H9 1.0000 . ?
C9 C8 1.543(3) . ?
C6 H6 0.9500 . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C2 H2 0.9500 . ?

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
O1 S1 O2 118.96(9) . . ?
C4 S1 O2 108.35(9) . . ?
C4 S1 O1 109.41(10) . . ?
C7 S1 O2 105.19(9) . . ?
C7 S1 O1 107.52(9) . . ?
C7 S1 C4 106.73(10) . . ?
F3 S2 F1 176.81(8) . . ?
F4 S2 F1 89.73(8) . . ?
F4 S2 F3 90.07(8) . . ?
F2 S2 F1 90.09(8) . . ?
F2 S2 F3 89.88(8) . . ?
F2 S2 F4 175.86(8) . . ?
F5 S2 F1 88.42(8) . . ?
F5 S2 F3 88.40(8) . . ?
F5 S2 F4 87.62(7) . . ?
F5 S2 F2 88.25(8) . . ?
O3 S2 F1 94.10(8) . . ?
O3 S2 F3 89.08(8) . . ?
O3 S2 F4 92.71(8) . . ?
O3 S2 F2 91.43(8) . . ?
O3 S2 F5 177.46(9) . . ?
C9 O3 S2 120.86(13) . . ?
C4 C5 H5 120.74(12) . . ?
C6 C5 H5 120.74(12) . . ?
C6 C5 C4 118.5(2) . . ?
C5 C4 S1 118.32(16) . . ?
C3 C4 S1 119.74(16) . . ?
C3 C4 C5 121.91(19) . . ?
H10b C10 H10a 111.2 . . ?
C7 C10 H10a 113.99(12) . . ?
C7 C10 H10b 113.99(11) . . ?
C9 C10 H10a 113.99(12) . . ?
C9 C10 H10b 113.99(12) . . ?
C9 C10 C7 87.96(15) . . ?
C6 C1 H1 119.80(13) . . ?
C2 C1 H1 119.80(13) . . ?
C2 C1 C6 120.4(2) . . ?
H3 C3 C4 120.76(12) . . ?
C2 C3 C4 118.48(19) . . ?
C2 C3 H3 120.76(12) . . ?
S1 C7 Br1 108.80(10) . . ?
C10 C7 Br1 117.16(15) . . ?
C10 C7 S1 114.18(15) . . ?
C8 C7 Br1 116.96(14) . . ?
C8 C7 S1 109.28(14) . . ?
C8 C7 C10 89.34(15) . . ?
C10 C9 O3 110.95(17) . . ?
H9 C9 O3 112.66(10) . . ?
H9 C9 C10 112.66(12) . . ?
C8 C9 O3 115.56(17) . . ?
C8 C9 C10 90.51(16) . . ?
C8 C9 H9 112.66(12) . . ?
C1 C6 C5 120.25(19) . . ?
H6 C6 C5 119.88(12) . . ?
H6 C6 C1 119.88(13) . . ?
C9 C8 C7 87.32(15) . . ?
H8a C8 C7 114.10(11) . . ?
H8a C8 C9 114.10(12) . . ?
H8b C8 C7 114.10(11) . . ?
H8b C8 C9 114.10(12) . . ?
H8b C8 H8a 111.3 . . ?
C3 C2 C1 120.4(2) . . ?
H2 C2 C1 119.78(13) . . ?
H2 C2 C3 119.78(12) . . ?

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
Br1 C7 C10 C9 -136.81(19) . . . . ?
Br1 C7 C8 C9 136.87(18) . . . . ?
S1 C4 C5 C6 -178.48(16) . . . . ?
S1 C4 C3 C2 178.99(17) . . . . ?
S1 C7 C10 C9 94.34(17) . . . . ?
S1 C7 C8 C9 -99.01(16) . . . . ?
S2 O3 C9 C10 166.01(16) . . . . ?
S2 O3 C9 C8 -92.83(15) . . . . ?
O3 C9 C10 C7 134.5(2) . . . . ?
O3 C9 C8 C7 -130.3(2) . . . . ?
C5 C4 C3 C2 0.8(2) . . . . ?
C5 C6 C1 C2 0.1(3) . . . . ?
C4 C3 C2 C1 -0.9(2) . . . . ?
C10 C7 C8 C9 16.45(17) . . . . ?
C10 C9 C8 C7 -16.65(16) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
