# Supplementary Information (SI) for ChemComm.
# 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_AS048B_polymorph1_major
_database_code_depnum_ccdc_archive 'CCDC 2394325'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;

#============================================================================== 

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H21 F3 N), O4 S, 4(H2 O)'
_chemical_formula_sum            'C28 H50 F6 N2 O8 S'
_chemical_formula_weight         688.76

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'
N N 0.0061 0.0033 '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'

_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                   15.9823(5)
_cell_length_b                   10.6216(3)
_cell_length_c                   21.5922(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.1193(10)
_cell_angle_gamma                90
_cell_volume                     3483.67(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9862
_cell_measurement_theta_min      2.3398
_cell_measurement_theta_max      28.1411

_exptl_crystal_description       'thin plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7091
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_source            'microfocus sealed tube'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            104065
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.985
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7991
_reflns_number_gt                5810
_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       'Bruker Instrument Service v8.5.0.11 RC8'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+1.7431P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7991
_refine_ls_number_parameters     604
_refine_ls_number_restraints     761
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.088
_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
S1 S 0.50053(3) 0.24934(4) 0.51077(2) 0.02763(11) Uani 1 1 d . . . . .
O1 O 0.42314(8) 0.24948(12) 0.45184(6) 0.0352(3) Uani 1 1 d . . . . .
O2 O 0.58244(8) 0.25317(12) 0.49314(6) 0.0345(3) Uani 1 1 d . . . . .
O3 O 0.49632(9) 0.36031(13) 0.54978(7) 0.0416(3) Uani 1 1 d . . . . .
O4 O 0.50056(9) 0.13390(13) 0.54777(7) 0.0434(3) Uani 1 1 d . . . . .
O5 O 0.60175(9) 0.44641(14) 0.41425(7) 0.0403(3) Uani 1 1 d D . . . .
HO5A H 0.5923(17) 0.387(2) 0.4393(11) 0.061 Uiso 1 1 d D U . . .
HO5B H 0.5855(16) 0.5161(19) 0.4289(12) 0.061 Uiso 1 1 d D U . . .
O6 O 0.47684(10) 0.40055(17) 0.29894(7) 0.0498(4) Uani 1 1 d D . . . .
HO6A H 0.5228(14) 0.413(3) 0.3334(11) 0.075 Uiso 1 1 d D U . . .
HO6B H 0.4781(19) 0.454(2) 0.2690(12) 0.075 Uiso 1 1 d D U . . .
O7 O 0.52594(10) 0.09759(18) 0.31205(7) 0.0496(4) Uani 1 1 d D . . . .
HO7A H 0.4815(15) 0.088(3) 0.3273(13) 0.074 Uiso 1 1 d D U . . .
HO7B H 0.519(2) 0.175(2) 0.2978(17) 0.074 Uiso 0.8 1 d D U P . .
HO7C H 0.505(9) 0.070(13) 0.273(3) 0.074 Uiso 0.2 1 d D U P . .
O8 O 0.40009(9) 0.04783(14) 0.36811(7) 0.0390(3) Uani 1 1 d D . . . .
HO8A H 0.4160(16) -0.0198(19) 0.3905(11) 0.059 Uiso 1 1 d D U . . .
HO8B H 0.4056(17) 0.107(2) 0.3966(10) 0.059 Uiso 1 1 d D U . . .
F1A F 0.9885(5) 0.8834(9) 0.8145(4) 0.080(2) Uani 0.444(3) 1 d D U P A 1
F2A F 0.9029(6) 0.8647(9) 0.8699(4) 0.076(2) Uani 0.444(3) 1 d D U P A 1
F3A F 1.0072(5) 0.7296(6) 0.8840(4) 0.091(2) Uani 0.444(3) 1 d D U P A 1
F1B F 0.9543(5) 0.9132(7) 0.8076(5) 0.073(2) Uani 0.393(3) 1 d D U P A 2
F2B F 0.9205(9) 0.8189(12) 0.8848(5) 0.088(3) Uani 0.393(3) 1 d D U P A 2
F3B F 1.0325(4) 0.7600(7) 0.8535(5) 0.082(2) Uani 0.393(3) 1 d D U P A 2
F1C F 0.9090(12) 0.9096(13) 0.8399(10) 0.098(4) Uani 0.163(3) 1 d D U P A 3
F2C F 0.9656(12) 0.7500(17) 0.8960(5) 0.072(3) Uani 0.163(3) 1 d D U P A 3
F3C F 1.0248(10) 0.812(2) 0.8270(8) 0.080(4) Uani 0.163(3) 1 d D U P A 3
F4A F -0.0446(4) 0.7873(6) 0.6125(4) 0.077(2) Uani 0.515(3) 1 d D U P B 1
F5A F 0.0656(5) 0.7201(7) 0.6921(3) 0.076(2) Uani 0.515(3) 1 d D U P B 1
F6A F 0.0233(4) 0.6217(5) 0.6011(3) 0.0552(13) Uani 0.515(3) 1 d D U P B 1
F4B F -0.0240(8) 0.8045(12) 0.6436(7) 0.074(3) Uani 0.284(3) 1 d D U P B 2
F5B F 0.0820(10) 0.6745(13) 0.6854(5) 0.072(3) Uani 0.284(3) 1 d D U P B 2
F6B F -0.0026(8) 0.6439(12) 0.5896(7) 0.081(3) Uani 0.284(3) 1 d D U P B 2
F4C F -0.0489(6) 0.7526(13) 0.5782(6) 0.074(3) Uani 0.201(3) 1 d D U P B 3
F5C F 0.0222(10) 0.7898(13) 0.6790(6) 0.078(3) Uani 0.201(3) 1 d D U P B 3
F6C F 0.0493(9) 0.6199(10) 0.6322(7) 0.075(3) Uani 0.201(3) 1 d D U P B 3
N1 N 0.62619(10) 0.52251(15) 0.61611(7) 0.0291(3) Uani 1 1 d D . . . .
HN1A H 0.6021(13) 0.543(2) 0.6482(9) 0.039(6) Uiso 1 1 d D . . . .
HN1B H 0.5907(12) 0.4609(17) 0.5913(9) 0.039(6) Uiso 1 1 d D . . . .
HN1C H 0.6198(14) 0.5952(17) 0.5920(10) 0.046(6) Uiso 1 1 d D . . . .
N2 N 0.36947(10) 0.97265(15) 0.55390(7) 0.0287(3) Uani 1 1 d D . . . .
HN2A H 0.3930(13) 0.950(2) 0.5967(8) 0.041(6) Uiso 1 1 d D . . . .
HN2B H 0.3730(15) 0.9012(17) 0.5311(10) 0.047(6) Uiso 1 1 d D . . . .
HN2C H 0.4093(13) 1.0295(18) 0.5458(10) 0.044(6) Uiso 1 1 d D . . . .
C1 C 0.71725(11) 0.46846(16) 0.64272(8) 0.0284(4) Uani 1 1 d D . . . .
C2 C 0.77469(11) 0.55765(17) 0.69344(8) 0.0294(4) Uani 1 1 d . . . . .
C3 C 0.85922(12) 0.5187(2) 0.72861(10) 0.0402(4) Uani 1 1 d . . . . .
H3 H 0.878526 0.437113 0.721153 0.048 Uiso 1 1 calc R U . . .
C4 C 0.91560(14) 0.5963(2) 0.77415(10) 0.0470(5) Uani 1 1 d . . . . .
H4 H 0.973201 0.568130 0.797533 0.056 Uiso 1 1 calc R U . . .
C5 C 0.88823(14) 0.7144(2) 0.78563(10) 0.0425(5) Uani 1 1 d . . . . .
C6 C 0.80511(14) 0.75582(19) 0.75040(10) 0.0407(4) Uani 1 1 d . . . . .
H6 H 0.786465 0.837929 0.757624 0.049 Uiso 1 1 calc R U . . .
C7 C 0.74895(13) 0.67799(18) 0.70464(9) 0.0357(4) Uani 1 1 d . . . . .
H7 H 0.691970 0.707366 0.680556 0.043 Uiso 1 1 calc R U . . .
C8 C 0.94763(17) 0.7984(3) 0.83570(12) 0.0599(6) Uani 1 1 d D . . . .
C9A C 0.75576(13) 0.44845(19) 0.58620(9) 0.0304(4) Uani 0.974(3) 1 d D U P C 1
H9A H 0.809973 0.397383 0.602728 0.036 Uiso 0.974(3) 1 calc R U P C 1
H9B H 0.713030 0.398244 0.552095 0.036 Uiso 0.974(3) 1 calc R U P C 1
C10A C 0.77813(13) 0.56582(18) 0.55430(10) 0.0358(5) Uani 0.974(3) 1 d D U P C
1
H10A H 0.818940 0.619408 0.587842 0.043 Uiso 0.974(3) 1 calc R U P C 1
H10B H 0.723795 0.614743 0.533924 0.043 Uiso 0.974(3) 1 calc R U P C 1
C11A C 0.82077(15) 0.5304(2) 0.50266(10) 0.0426(5) Uani 0.974(3) 1 d D U P C 1
H11A H 0.872152 0.476855 0.522219 0.064 Uiso 0.974(3) 1 calc R U P C 1
H11B H 0.839376 0.606975 0.485272 0.064 Uiso 0.974(3) 1 calc R U P C 1
H11C H 0.778205 0.484565 0.467262 0.064 Uiso 0.974(3) 1 calc R U P C 1
C9B C 0.745(4) 0.497(8) 0.581(2) 0.032(3) Uani 0.026(3) 1 d D U P C 2
H9C H 0.698220 0.464900 0.542691 0.038 Uiso 0.026(3) 1 calc R U P C 2
H9D H 0.747312 0.589299 0.576498 0.038 Uiso 0.026(3) 1 calc R U P C 2
C10B C 0.832(4) 0.444(6) 0.579(2) 0.033(3) Uani 0.026(3) 1 d D U P C 2
H10C H 0.834298 0.352938 0.589200 0.040 Uiso 0.026(3) 1 calc R U P C 2
H10D H 0.880505 0.486085 0.611893 0.040 Uiso 0.026(3) 1 calc R U P C 2
C11B C 0.844(4) 0.461(8) 0.512(3) 0.037(6) Uani 0.026(3) 1 d D U P C 2
H11D H 0.832843 0.380753 0.488331 0.056 Uiso 0.026(3) 1 calc R U P C 2
H11E H 0.905014 0.487369 0.517784 0.056 Uiso 0.026(3) 1 calc R U P C 2
H11F H 0.803472 0.524955 0.487434 0.056 Uiso 0.026(3) 1 calc R U P C 2
C12 C 0.70772(12) 0.33867(17) 0.67117(9) 0.0326(4) Uani 1 1 d . . . . .
H12A H 0.669796 0.286177 0.635538 0.039 Uiso 1 1 calc R U . . .
H12B H 0.766607 0.298746 0.685596 0.039 Uiso 1 1 calc R U . . .
C13 C 0.67029(15) 0.33415(19) 0.72762(10) 0.0427(5) Uani 1 1 d . . . . .
H13A H 0.611518 0.374430 0.714488 0.051 Uiso 1 1 calc R U . . .
H13B H 0.709100 0.382070 0.764861 0.051 Uiso 1 1 calc R U . . .
C14 C 0.66230(18) 0.1993(2) 0.74854(11) 0.0538(6) Uani 1 1 d . . . . .
H14A H 0.619997 0.153759 0.712882 0.081 Uiso 1 1 calc R U . . .
H14B H 0.641862 0.199219 0.786883 0.081 Uiso 1 1 calc R U . . .
H14C H 0.719886 0.158024 0.759348 0.081 Uiso 1 1 calc R U . . .
C15 C 0.28057(11) 1.03470(16) 0.53832(8) 0.0282(3) Uani 1 1 d . . . . .
C16 C 0.21876(11) 0.95378(16) 0.56255(8) 0.0289(4) Uani 1 1 d . . . . .
C17 C 0.23620(12) 0.82927(17) 0.58195(9) 0.0343(4) Uani 1 1 d . . . . .
H17 H 0.289950 0.791786 0.581432 0.041 Uiso 1 1 calc R U . . .
C18 C 0.17661(13) 0.75927(18) 0.60197(10) 0.0381(4) Uani 1 1 d . . . . .
H18 H 0.189632 0.674255 0.615112 0.046 Uiso 1 1 calc R U . . .
C19 C 0.09784(13) 0.81230(19) 0.60299(10) 0.0386(4) Uani 1 1 d . . . . .
C20 C 0.07851(13) 0.9351(2) 0.58239(11) 0.0430(5) Uani 1 1 d . . . . .
H20 H 0.024069 0.971633 0.581950 0.052 Uiso 1 1 calc R U . . .
C21 C 0.13847(12) 1.00461(19) 0.56245(10) 0.0383(4) Uani 1 1 d . . . . .
H21 H 0.124627 1.088960 0.548345 0.046 Uiso 1 1 calc R U . . .
C22 C 0.03555(16) 0.7372(2) 0.62721(13) 0.0547(6) Uani 1 1 d D . . . .
C23 C 0.29635(12) 1.16483(17) 0.57099(8) 0.0317(4) Uani 1 1 d . . . . .
H23A H 0.337486 1.211815 0.553432 0.038 Uiso 1 1 calc R U . . .
H23B H 0.239777 1.211103 0.557981 0.038 Uiso 1 1 calc R U . . .
C24 C 0.33305(15) 1.16660(19) 0.64508(9) 0.0410(5) Uani 1 1 d . . . . .
H24A H 0.289521 1.128943 0.663720 0.049 Uiso 1 1 calc R U . . .
H24B H 0.387294 1.115037 0.659264 0.049 Uiso 1 1 calc R U . . .
C25 C 0.35376(17) 1.2995(2) 0.67043(11) 0.0526(6) Uani 1 1 d . . . . .
H25A H 0.400539 1.334255 0.655044 0.079 Uiso 1 1 calc R U . . .
H25B H 0.373311 1.298505 0.718181 0.079 Uiso 1 1 calc R U . . .
H25C H 0.300850 1.351697 0.654489 0.079 Uiso 1 1 calc R U . . .
C26 C 0.24381(12) 1.05221(17) 0.46390(8) 0.0313(4) Uani 1 1 d . . . . .
H26A H 0.192195 1.108912 0.454467 0.038 Uiso 1 1 calc R U . . .
H26B H 0.289126 1.095471 0.449174 0.038 Uiso 1 1 calc R U . . .
C27 C 0.21608(13) 0.93341(18) 0.42333(9) 0.0379(4) Uani 1 1 d . . . . .
H27A H 0.170627 0.888697 0.437278 0.045 Uiso 1 1 calc R U . . .
H27B H 0.267452 0.876771 0.430730 0.045 Uiso 1 1 calc R U . . .
C28 C 0.17947(14) 0.9648(2) 0.35093(9) 0.0436(5) Uani 1 1 d . . . . .
H28A H 0.132451 1.027404 0.344143 0.065 Uiso 1 1 calc R U . . .
H28B H 0.155795 0.888200 0.326398 0.065 Uiso 1 1 calc R U . . .
H28C H 0.226648 0.998808 0.335757 0.065 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4625(13) . ?
S1 O4 1.4633(13) . ?
S1 O1 1.4730(12) . ?
S1 O2 1.4732(13) . ?
O5 HO5A 0.873(16) . ?
O5 HO5B 0.876(16) . ?
O6 HO6A 0.878(17) . ?
O6 HO6B 0.865(17) . ?
O7 HO7A 0.877(17) . ?
O7 HO7B 0.870(18) . ?
O7 HO7C 0.86(2) . ?
O8 HO8A 0.859(16) . ?
O8 HO8B 0.862(16) . ?
F1A C8 1.280(7) . ?
F2A C8 1.371(7) . ?
F3A C8 1.382(6) . ?
F1B C8 1.381(8) . ?
F2B C8 1.284(9) . ?
F3B C8 1.352(6) . ?
F1C C8 1.349(11) . ?
F2C C8 1.345(11) . ?
F3C C8 1.313(11) . ?
F4A C22 1.331(6) . ?
F5A C22 1.344(6) . ?
F6A C22 1.339(6) . ?
F4B C22 1.324(10) . ?
F5B C22 1.412(10) . ?
F6B C22 1.306(10) . ?
F4C C22 1.442(9) . ?
F5C C22 1.325(9) . ?
F6C C22 1.263(10) . ?
N1 C1 1.503(2) . ?
N1 HN1A 0.916(15) . ?
N1 HN1B 0.921(15) . ?
N1 HN1C 0.920(16) . ?
N2 C15 1.506(2) . ?
N2 HN2A 0.916(15) . ?
N2 HN2B 0.915(16) . ?
N2 HN2C 0.932(16) . ?
C1 C2 1.521(2) . ?
C1 C12 1.536(2) . ?
C1 C9A 1.543(2) . ?
C1 C9B 1.56(2) . ?
C2 C7 1.387(3) . ?
C2 C3 1.391(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 C8 1.492(3) . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9A C10A 1.520(3) . ?
C9A H9A 0.9900 . ?
C9A H9B 0.9900 . ?
C10A C11A 1.524(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C9B C10B 1.51(2) . ?
C9B H9C 0.9900 . ?
C9B H9D 0.9900 . ?
C10B C11B 1.52(2) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12 C13 1.516(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.519(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.520(2) . ?
C15 C23 1.537(2) . ?
C15 C26 1.541(2) . ?
C16 C17 1.389(3) . ?
C16 C21 1.392(2) . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(3) . ?
C19 C22 1.492(3) . ?
C20 C21 1.380(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C23 C24 1.523(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.513(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.521(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.526(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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
O3 S1 O4 110.68(9) . . ?
O3 S1 O1 108.67(8) . . ?
O4 S1 O1 109.27(8) . . ?
O3 S1 O2 109.28(8) . . ?
O4 S1 O2 108.34(8) . . ?
O1 S1 O2 110.59(8) . . ?
HO5A O5 HO5B 105(2) . . ?
HO6A O6 HO6B 109(3) . . ?
HO7A O7 HO7B 102(3) . . ?
HO7A O7 HO7C 102(10) . . ?
HO8A O8 HO8B 105(2) . . ?
C1 N1 HN1A 112.6(13) . . ?
C1 N1 HN1B 107.4(13) . . ?
HN1A N1 HN1B 106.1(18) . . ?
C1 N1 HN1C 117.5(14) . . ?
HN1A N1 HN1C 103.6(19) . . ?
HN1B N1 HN1C 109.1(19) . . ?
C15 N2 HN2A 113.8(14) . . ?
C15 N2 HN2B 117.0(14) . . ?
HN2A N2 HN2B 104.3(19) . . ?
C15 N2 HN2C 109.0(13) . . ?
HN2A N2 HN2C 105.8(19) . . ?
HN2B N2 HN2C 106.1(19) . . ?
N1 C1 C2 109.47(14) . . ?
N1 C1 C12 106.93(14) . . ?
C2 C1 C12 112.57(14) . . ?
N1 C1 C9A 109.10(14) . . ?
C2 C1 C9A 110.81(15) . . ?
C12 C1 C9A 107.83(14) . . ?
N1 C1 C9B 96(2) . . ?
C2 C1 C9B 103(3) . . ?
C12 C1 C9B 127(3) . . ?
C7 C2 C3 118.00(17) . . ?
C7 C2 C1 123.65(16) . . ?
C3 C2 C1 118.28(16) . . ?
C4 C3 C2 121.27(19) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.75(18) . . ?
C4 C5 C8 120.6(2) . . ?
C6 C5 C8 119.7(2) . . ?
C5 C6 C7 120.14(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 120.90(18) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
F3C C8 F2C 104.8(9) . . ?
F3C C8 F1C 112.3(11) . . ?
F2C C8 F1C 103.5(10) . . ?
F2B C8 F3B 112.5(6) . . ?
F1A C8 F2A 103.8(6) . . ?
F2B C8 F1B 107.7(7) . . ?
F3B C8 F1B 100.6(5) . . ?
F1A C8 F3A 109.5(5) . . ?
F2A C8 F3A 102.6(5) . . ?
F1A C8 C5 116.3(5) . . ?
F2B C8 C5 113.5(6) . . ?
F3C C8 C5 112.2(8) . . ?
F2C C8 C5 111.7(6) . . ?
F1C C8 C5 111.8(6) . . ?
F3B C8 C5 112.5(3) . . ?
F2A C8 C5 112.1(5) . . ?
F1B C8 C5 109.2(4) . . ?
F3A C8 C5 111.4(3) . . ?
C10A C9A C1 116.97(16) . . ?
C10A C9A H9A 108.1 . . ?
C1 C9A H9A 108.1 . . ?
C10A C9A H9B 108.1 . . ?
C1 C9A H9B 108.1 . . ?
H9A C9A H9B 107.3 . . ?
C9A C10A C11A 110.54(17) . . ?
C9A C10A H10A 109.5 . . ?
C11A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C11A C10A H10B 109.5 . . ?
H10A C10A H10B 108.1 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10B C9B C1 118(4) . . ?
C10B C9B H9C 107.8 . . ?
C1 C9B H9C 107.8 . . ?
C10B C9B H9D 107.8 . . ?
C1 C9B H9D 107.8 . . ?
H9C C9B H9D 107.1 . . ?
C9B C10B C11B 113(3) . . ?
C9B C10B H10C 109.1 . . ?
C11B C10B H10C 109.1 . . ?
C9B C10B H10D 109.1 . . ?
C11B C10B H10D 109.1 . . ?
H10C C10B H10D 107.8 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C13 C12 C1 117.56(15) . . ?
C13 C12 H12A 107.9 . . ?
C1 C12 H12A 107.9 . . ?
C13 C12 H12B 107.9 . . ?
C1 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
C12 C13 C14 111.07(17) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 110.15(14) . . ?
N2 C15 C23 106.40(14) . . ?
C16 C15 C23 112.46(14) . . ?
N2 C15 C26 108.25(14) . . ?
C16 C15 C26 110.45(14) . . ?
C23 C15 C26 108.97(14) . . ?
C17 C16 C21 117.92(17) . . ?
C17 C16 C15 123.46(16) . . ?
C21 C16 C15 118.55(16) . . ?
C18 C17 C16 120.95(17) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.34(18) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 119.47(18) . . ?
C20 C19 C22 120.73(19) . . ?
C18 C19 C22 119.79(19) . . ?
C21 C20 C19 119.86(18) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C16 121.43(18) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
F6B C22 F4B 109.9(8) . . ?
F6C C22 F5C 114.4(9) . . ?
F4A C22 F6A 105.2(4) . . ?
F4A C22 F5A 108.0(5) . . ?
F6A C22 F5A 105.8(4) . . ?
F6B C22 F5B 102.1(8) . . ?
F4B C22 F5B 103.8(7) . . ?
F6C C22 F4C 105.8(8) . . ?
F5C C22 F4C 102.2(7) . . ?
F6C C22 C19 116.1(7) . . ?
F6B C22 C19 114.9(8) . . ?
F4B C22 C19 114.8(7) . . ?
F5C C22 C19 111.7(5) . . ?
F4A C22 C19 113.5(4) . . ?
F6A C22 C19 111.6(4) . . ?
F5A C22 C19 112.1(4) . . ?
F5B C22 C19 109.9(7) . . ?
F4C C22 C19 104.8(6) . . ?
C24 C23 C15 116.62(15) . . ?
C24 C23 H23A 108.1 . . ?
C15 C23 H23A 108.1 . . ?
C24 C23 H23B 108.1 . . ?
C15 C23 H23B 108.1 . . ?
H23A C23 H23B 107.3 . . ?
C25 C24 C23 111.16(17) . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C15 116.66(15) . . ?
C27 C26 H26A 108.1 . . ?
C15 C26 H26A 108.1 . . ?
C27 C26 H26B 108.1 . . ?
C15 C26 H26B 108.1 . . ?
H26A C26 H26B 107.3 . . ?
C26 C27 C28 111.05(16) . . ?
C26 C27 H27A 109.4 . . ?
C28 C27 H27A 109.4 . . ?
C26 C27 H27B 109.4 . . ?
C28 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C7 -9.2(2) . . . . ?
C12 C1 C2 C7 -127.99(18) . . . . ?
C9A C1 C2 C7 111.2(2) . . . . ?
C9B C1 C2 C7 92(2) . . . . ?
N1 C1 C2 C3 173.72(16) . . . . ?
C12 C1 C2 C3 54.9(2) . . . . ?
C9A C1 C2 C3 -65.9(2) . . . . ?
C9B C1 C2 C3 -85(2) . . . . ?
C7 C2 C3 C4 1.0(3) . . . . ?
C1 C2 C3 C4 178.29(19) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C3 C4 C5 C8 178.7(2) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C8 C5 C6 C7 -178.9(2) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C3 C2 C7 C6 -1.3(3) . . . . ?
C1 C2 C7 C6 -178.39(18) . . . . ?
C4 C5 C8 F1A 99.5(6) . . . . ?
C6 C5 C8 F1A -80.3(6) . . . . ?
C4 C5 C8 F2B -113.1(7) . . . . ?
C6 C5 C8 F2B 67.1(7) . . . . ?
C4 C5 C8 F3C 53.0(12) . . . . ?
C6 C5 C8 F3C -126.9(12) . . . . ?
C4 C5 C8 F2C -64.3(11) . . . . ?
C6 C5 C8 F2C 115.8(11) . . . . ?
C4 C5 C8 F1C -179.8(13) . . . . ?
C6 C5 C8 F1C 0.3(13) . . . . ?
C4 C5 C8 F3B 16.1(6) . . . . ?
C6 C5 C8 F3B -163.8(6) . . . . ?
C4 C5 C8 F2A -141.3(5) . . . . ?
C6 C5 C8 F2A 38.9(6) . . . . ?
C4 C5 C8 F1B 126.8(5) . . . . ?
C6 C5 C8 F1B -53.1(5) . . . . ?
C4 C5 C8 F3A -26.9(6) . . . . ?
C6 C5 C8 F3A 153.2(6) . . . . ?
N1 C1 C9A C10A 69.2(2) . . . . ?
C2 C1 C9A C10A -51.4(2) . . . . ?
C12 C1 C9A C10A -174.98(16) . . . . ?
C1 C9A C10A C11A 176.33(17) . . . . ?
N1 C1 C9B C10B -172(6) . . . . ?
C2 C1 C9B C10B 76(7) . . . . ?
C12 C1 C9B C10B -56(8) . . . . ?
C1 C9B C10B C11B 171(6) . . . . ?
N1 C1 C12 C13 -62.4(2) . . . . ?
C2 C1 C12 C13 57.8(2) . . . . ?
C9A C1 C12 C13 -179.64(17) . . . . ?
C9B C1 C12 C13 -174(3) . . . . ?
C1 C12 C13 C14 178.10(18) . . . . ?
N2 C15 C16 C17 -13.7(2) . . . . ?
C23 C15 C16 C17 -132.25(18) . . . . ?
C26 C15 C16 C17 105.77(19) . . . . ?
N2 C15 C16 C21 169.47(16) . . . . ?
C23 C15 C16 C21 51.0(2) . . . . ?
C26 C15 C16 C21 -71.0(2) . . . . ?
C21 C16 C17 C18 -1.5(3) . . . . ?
C15 C16 C17 C18 -178.32(17) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C17 C18 C19 C20 1.5(3) . . . . ?
C17 C18 C19 C22 -177.6(2) . . . . ?
C18 C19 C20 C21 -1.5(3) . . . . ?
C22 C19 C20 C21 177.6(2) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?
C17 C16 C21 C20 1.5(3) . . . . ?
C15 C16 C21 C20 178.47(18) . . . . ?
C20 C19 C22 F6C 165.9(8) . . . . ?
C18 C19 C22 F6C -15.0(8) . . . . ?
C20 C19 C22 F6B 111.6(6) . . . . ?
C18 C19 C22 F6B -69.4(7) . . . . ?
C20 C19 C22 F4B -17.4(7) . . . . ?
C18 C19 C22 F4B 161.7(7) . . . . ?
C20 C19 C22 F5C -60.4(9) . . . . ?
C18 C19 C22 F5C 118.7(9) . . . . ?
C20 C19 C22 F4A 15.0(5) . . . . ?
C18 C19 C22 F4A -165.9(4) . . . . ?
C20 C19 C22 F6A 133.8(3) . . . . ?
C18 C19 C22 F6A -47.2(4) . . . . ?
C20 C19 C22 F5A -107.7(4) . . . . ?
C18 C19 C22 F5A 71.3(4) . . . . ?
C20 C19 C22 F5B -133.9(6) . . . . ?
C18 C19 C22 F5B 45.1(6) . . . . ?
C20 C19 C22 F4C 49.6(6) . . . . ?
C18 C19 C22 F4C -131.4(6) . . . . ?
N2 C15 C23 C24 -63.4(2) . . . . ?
C16 C15 C23 C24 57.3(2) . . . . ?
C26 C15 C23 C24 -179.90(16) . . . . ?
C15 C23 C24 C25 174.44(18) . . . . ?
N2 C15 C26 C27 70.1(2) . . . . ?
C16 C15 C26 C27 -50.6(2) . . . . ?
C23 C15 C26 C27 -174.60(16) . . . . ?
C15 C26 C27 C28 178.92(16) . . . . ?

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
N1 HN1A O6 0.916(15) 2.039(16) 2.936(2) 166.2(19) 3_666 yes
N1 HN1B O3 0.921(15) 1.838(16) 2.735(2) 163.8(19) . yes
N1 HN1C O1 0.920(16) 1.919(17) 2.814(2) 164(2) 3_666 yes
N2 HN2A O7 0.916(15) 2.056(16) 2.953(2) 166.1(19) 3_666 yes
N2 HN2B O2 0.915(16) 1.924(17) 2.804(2) 160(2) 3_666 yes
N2 HN2C O4 0.932(16) 1.822(16) 2.741(2) 168(2) 1_565 yes
O5 HO5A O2 0.873(16) 1.875(17) 2.7451(19) 174(3) . yes
O5 HO5B O3 0.876(16) 2.004(18) 2.834(2) 158(2) 3_666 yes
O6 HO6A O5 0.878(17) 1.842(18) 2.707(2) 168(3) . yes
O6 HO6B O7 0.865(17) 2.308(18) 3.172(3) 177(3) 2_655 yes
O7 HO7A O8 0.877(17) 1.834(18) 2.703(2) 171(3) . yes
O7 HO7B O6 0.870(18) 2.49(2) 3.303(3) 155(3) . yes
O7 HO7C O6 0.86(2) 2.45(9) 3.172(3) 142(13) 2_645 yes
O8 HO8A O4 0.859(16) 1.980(18) 2.7843(19) 156(2) 3_656 yes
O8 HO8B O1 0.862(16) 1.896(17) 2.7528(19) 172(2) . yes

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.050



####################################################################### 
# 
# 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_AS048C_polymorph2_minor
_database_code_depnum_ccdc_archive 'CCDC 2394326'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;

#============================================================================== 

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 F3 N, 0.5(O4 S), H2 O'
_chemical_formula_sum            'C14 H23 F3 N O3 S0.50'
_chemical_formula_weight         326.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'

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

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

_cell_length_a                   29.6157(17)
_cell_length_b                   8.9695(5)
_cell_length_c                   12.2342(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3249.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      5.9766
_cell_measurement_theta_max      74.4819

_exptl_crystal_description       'flat rod'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             1384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    1.560
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_source            'microfocus sealed tube'
_diffrn_source_power             0.06
_diffrn_source_current           1.1
_diffrn_source_voltage           50
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            17526
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.152
_diffrn_reflns_theta_max         74.571
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3303
_reflns_number_gt                3199
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_max     0.951
_reflns_Friedel_fraction_full    0.960

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker Instrument Service v8.5.0.11 RC8'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+1.0236P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.11(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3303
_refine_ls_number_parameters     265
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.076
_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
S1 S 0.000000 0.57969(8) 0.23708(5) 0.02543(16) Uani 1 2 d S T P . .
O1 O 0.000000 0.5207(3) 0.35104(16) 0.0337(5) Uani 1 2 d S T P . .
O2 O -0.0444(2) 0.5571(7) 0.1925(5) 0.0384(13) Uani 0.5 1 d . . P . .
O3 O 0.01222(10) 0.7394(4) 0.2407(3) 0.0451(10) Uani 0.5 1 d . . P . .
O4 O 0.0344(2) 0.5019(8) 0.1719(6) 0.0495(15) Uani 0.5 1 d . . P . .
O5 O 0.0099(4) 0.8510(5) 0.4583(4) 0.076(4) Uani 0.5 1 d D . P . .
HO5A H 0.000000 0.784(6) 0.498(5) 0.115 Uiso 1 2 d DS U P . .
HO5B H 0.015(3) 0.811(8) 0.401(4) 0.115 Uiso 0.5 1 d D U P . .
O6 O 0.000000 0.1436(3) 0.53118(17) 0.0343(5) Uani 1 2 d DS T P . .
HO6A H 0.000000 0.155(5) 0.5955(18) 0.051 Uiso 1 2 d DS U P . .
HO6B H 0.000000 0.057(2) 0.518(4) 0.051 Uiso 1 2 d DS U P . .
F1A F 0.2204(6) -0.0974(13) 0.7226(11) 0.056(3) Uani 0.5 1 d D U P A 1
F2A F 0.2374(5) 0.0982(15) 0.8102(10) 0.059(3) Uani 0.5 1 d D U P A 1
F3A F 0.2759(7) 0.034(3) 0.6716(19) 0.068(4) Uani 0.5 1 d D U P A 1
F1B F 0.2269(6) -0.1002(12) 0.7115(12) 0.059(3) Uani 0.5 1 d D U P A 2
F2B F 0.2312(4) 0.0844(16) 0.8178(10) 0.058(3) Uani 0.5 1 d D U P A 2
F3B F 0.2775(7) 0.067(2) 0.6865(18) 0.055(3) Uani 0.5 1 d D U P A 2
N1 N 0.06308(5) 0.37544(19) 0.47759(13) 0.0234(3) Uani 1 1 d D . . . .
HN1A H 0.0504(9) 0.288(2) 0.485(2) 0.035 Uiso 1 1 d D U . . .
HN1B H 0.0473(9) 0.428(3) 0.431(2) 0.035 Uiso 1 1 d D U . . .
HN1C H 0.0623(9) 0.419(3) 0.5412(17) 0.035 Uiso 1 1 d D U . . .
C1 C 0.10978(6) 0.3666(2) 0.42929(14) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.14126(7) 0.2811(2) 0.50564(16) 0.0249(4) Uani 1 1 d . . . . .
C3 C 0.18323(7) 0.2356(3) 0.46616(17) 0.0352(5) Uani 1 1 d . . . . .
H3 H 0.191121 0.257126 0.392565 0.042 Uiso 1 1 calc R U . . .
C4 C 0.21372(7) 0.1598(3) 0.53175(19) 0.0354(5) Uani 1 1 d . . . . .
H4 H 0.241953 0.128388 0.502953 0.042 Uiso 1 1 calc R U . . .
C5 C 0.20270(7) 0.1302(2) 0.63951(17) 0.0276(4) Uani 1 1 d . . . . .
C6 C 0.16146(7) 0.1753(3) 0.68059(17) 0.0323(4) Uani 1 1 d . . . . .
H6 H 0.153995 0.155249 0.754661 0.039 Uiso 1 1 calc R U . . .
C7 C 0.13079(7) 0.2500(2) 0.61412(16) 0.0295(4) Uani 1 1 d . . . . .
H7 H 0.102453 0.280127 0.643057 0.035 Uiso 1 1 calc R U . . .
C8 C 0.23435(7) 0.0445(3) 0.7115(2) 0.0362(5) Uani 1 1 d . . . . .
C9 C 0.12639(7) 0.5279(2) 0.41354(16) 0.0289(4) Uani 1 1 d . . . . .
H9A H 0.156210 0.524813 0.377048 0.035 Uiso 1 1 calc R U . . .
H9B H 0.105230 0.579592 0.363672 0.035 Uiso 1 1 calc R U . . .
C10 C 0.13082(9) 0.6203(3) 0.51788(19) 0.0367(5) Uani 1 1 d . . . . .
H10A H 0.100751 0.630194 0.552461 0.044 Uiso 1 1 calc R U . . .
H10B H 0.150837 0.567448 0.569852 0.044 Uiso 1 1 calc R U . . .
C11 C 0.14986(11) 0.7745(3) 0.4957(2) 0.0492(6) Uani 1 1 d . . . . .
H11A H 0.179439 0.765193 0.460413 0.074 Uiso 1 1 calc R U . . .
H11B H 0.153141 0.828556 0.564818 0.074 Uiso 1 1 calc R U . . .
H11C H 0.129286 0.829215 0.447448 0.074 Uiso 1 1 calc R U . . .
C12 C 0.10421(7) 0.2888(2) 0.31792(16) 0.0309(4) Uani 1 1 d . . . . .
H12A H 0.082059 0.345927 0.274092 0.037 Uiso 1 1 calc R U . . .
H12B H 0.133476 0.292858 0.278921 0.037 Uiso 1 1 calc R U . . .
C13 C 0.08880(10) 0.1269(3) 0.3229(2) 0.0454(6) Uani 1 1 d . . . . .
H13A H 0.114978 0.063029 0.341363 0.054 Uiso 1 1 calc R U . . .
H13B H 0.066201 0.115965 0.382004 0.054 Uiso 1 1 calc R U . . .
C14 C 0.06843(11) 0.0736(4) 0.2170(3) 0.0649(9) Uani 1 1 d . . . . .
H14A H 0.042004 0.134683 0.199151 0.097 Uiso 1 1 calc R U . . .
H14B H 0.059212 -0.030864 0.224541 0.097 Uiso 1 1 calc R U . . .
H14C H 0.090821 0.082212 0.158337 0.097 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.439(7) . ?
S1 O4 1.471(7) . ?
S1 O3 1.478(3) . ?
S1 O1 1.491(2) . ?
O5 HO5A 0.83(2) . ?
O5 HO5B 0.80(2) . ?
O6 HO6A 0.79(2) . ?
O6 HO6B 0.80(2) . ?
F1A C8 1.345(12) . ?
F2A C8 1.303(11) . ?
F3A C8 1.33(2) . ?
F1B C8 1.317(11) . ?
F2B C8 1.353(11) . ?
F3B C8 1.33(2) . ?
N1 C1 1.506(2) . ?
N1 HN1A 0.875(18) . ?
N1 HN1B 0.872(18) . ?
N1 HN1C 0.872(18) . ?
C1 C2 1.526(3) . ?
C1 C12 1.539(3) . ?
C1 C9 1.540(3) . ?
C2 C7 1.391(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 C8 1.498(3) . ?
C6 C7 1.391(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.528(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.518(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.524(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.508(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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 O4 111.2(4) . . ?
O2 S1 O3 111.8(3) . . ?
O4 S1 O3 107.8(3) . . ?
O2 S1 O1 107.7(3) . . ?
O4 S1 O1 109.8(3) . . ?
O3 S1 O1 108.44(17) . . ?
HO5A O5 HO5B 104(5) . . ?
HO6A O6 HO6B 109(4) . . ?
C1 N1 HN1A 112.6(19) . . ?
C1 N1 HN1B 105.4(19) . . ?
HN1A N1 HN1B 108(3) . . ?
C1 N1 HN1C 113.4(18) . . ?
HN1A N1 HN1C 108(3) . . ?
HN1B N1 HN1C 109(2) . . ?
N1 C1 C2 110.32(15) . . ?
N1 C1 C12 105.83(15) . . ?
C2 C1 C12 112.31(16) . . ?
N1 C1 C9 107.01(16) . . ?
C2 C1 C9 110.71(16) . . ?
C12 C1 C9 110.42(16) . . ?
C7 C2 C3 118.08(18) . . ?
C7 C2 C1 123.24(17) . . ?
C3 C2 C1 118.64(17) . . ?
C4 C3 C2 121.57(19) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 119.92(19) . . ?
C6 C5 C8 119.32(19) . . ?
C4 C5 C8 120.7(2) . . ?
C5 C6 C7 120.38(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 120.57(18) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
F2A C8 F3A 107.7(11) . . ?
F1B C8 F3B 108.3(12) . . ?
F2A C8 F1A 106.1(9) . . ?
F3A C8 F1A 104.6(12) . . ?
F1B C8 F2B 104.4(9) . . ?
F3B C8 F2B 104.3(10) . . ?
F2A C8 C5 113.5(7) . . ?
F1B C8 C5 113.6(7) . . ?
F3A C8 C5 113.7(12) . . ?
F3B C8 C5 112.8(11) . . ?
F1A C8 C5 110.7(6) . . ?
F2B C8 C5 112.7(6) . . ?
C10 C9 C1 115.63(16) . . ?
C10 C9 H9A 108.4 . . ?
C1 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C1 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C11 C10 C9 112.1(2) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C1 115.36(17) . . ?
C13 C12 H12A 108.4 . . ?
C1 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C1 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C12 112.8(2) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C7 -14.6(3) . . . . ?
C12 C1 C2 C7 -132.4(2) . . . . ?
C9 C1 C2 C7 103.6(2) . . . . ?
N1 C1 C2 C3 167.48(19) . . . . ?
C12 C1 C2 C3 49.7(3) . . . . ?
C9 C1 C2 C3 -74.2(2) . . . . ?
C7 C2 C3 C4 0.9(4) . . . . ?
C1 C2 C3 C4 178.9(2) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 C8 178.2(2) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C8 C5 C6 C7 -177.5(2) . . . . ?
C3 C2 C7 C6 -0.2(3) . . . . ?
C1 C2 C7 C6 -178.1(2) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C6 C5 C8 F2A -43.6(7) . . . . ?
C4 C5 C8 F2A 138.7(7) . . . . ?
C6 C5 C8 F1B 86.0(9) . . . . ?
C4 C5 C8 F1B -91.8(9) . . . . ?
C6 C5 C8 F3A -167.1(9) . . . . ?
C4 C5 C8 F3A 15.2(9) . . . . ?
C6 C5 C8 F3B -150.3(9) . . . . ?
C4 C5 C8 F3B 31.9(10) . . . . ?
C6 C5 C8 F1A 75.6(8) . . . . ?
C4 C5 C8 F1A -102.2(8) . . . . ?
C6 C5 C8 F2B -32.5(7) . . . . ?
C4 C5 C8 F2B 149.7(7) . . . . ?
N1 C1 C9 C10 62.0(2) . . . . ?
C2 C1 C9 C10 -58.2(2) . . . . ?
C12 C1 C9 C10 176.77(17) . . . . ?
C1 C9 C10 C11 176.8(2) . . . . ?
N1 C1 C12 C13 -65.7(2) . . . . ?
C2 C1 C12 C13 54.7(2) . . . . ?
C9 C1 C12 C13 178.79(19) . . . . ?
C1 C12 C13 C14 159.8(2) . . . . ?

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
N1 HN1A O6 0.875(18) 2.06(2) 2.871(2) 155(3) . yes
N1 HN1B O1 0.872(18) 1.902(19) 2.754(2) 165(3) . yes
N1 HN1C O2 0.872(18) 1.94(2) 2.754(7) 155(3) 2_565 yes
N1 HN1C O4 0.872(18) 1.93(2) 2.753(7) 156(3) 3_565 yes
O5 HO5B O3 0.80(2) 2.07(3) 2.845(5) 164(10) . yes
O6 HO6A O3 0.79(2) 2.05(2) 2.793(4) 157(4) 2_565 yes
O6 HO6A O3 0.79(2) 2.05(2) 2.793(4) 157(4) 3_565 yes
O6 HO6B O5 0.80(2) 2.01(2) 2.788(5) 167(4) 1_545 yes
O6 HO6B O5 0.80(2) 2.01(2) 2.788(5) 167(4) 4_545 yes

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.037



