# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_bau25
_database_code_depnum_ccdc_archive 'CCDC 2018541'
loop_
_audit_author_name
_audit_author_address
'Helge Mueller-Bunz'
;University College Dublin, School of Chemistry
Republic of Ireland
;
_audit_update_record             
;
2020-07-23 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 F3 N O3 S'
_chemical_formula_sum            'C18 H18 F3 N O3 S'
_chemical_formula_weight         385.39

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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.6871(3)
_cell_length_b                   8.6686(4)
_cell_length_c                   18.3693(7)
_cell_angle_alpha                81.037(4)
_cell_angle_beta                 88.297(4)
_cell_angle_gamma                87.959(4)
_cell_volume                     893.70(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3083
_cell_measurement_theta_min      4.8410
_cell_measurement_theta_max      76.5350

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.531
_exptl_crystal_size_mid          0.366
_exptl_crystal_size_min          0.109
_exptl_absorpt_coefficient_mu    2.054
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_reflns_number            7693
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.876
_diffrn_reflns_theta_max         76.741
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3684
_reflns_number_gt                3246
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0719P)²+0.5252P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3684
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0431(4) 0.7004(2) 0.24717(11) 0.0269(4) Uani 1 1 d . . . . .
C2 C 1.1973(4) 0.8002(3) 0.20549(13) 0.0386(5) Uani 1 1 d . . . . .
H2 H 1.326592 0.839803 0.227612 0.046 Uiso 1 1 calc R U . . .
C3 C 1.1588(5) 0.8415(4) 0.13035(15) 0.0507(7) Uani 1 1 d . . . . .
H3 H 1.263613 0.909201 0.100703 0.061 Uiso 1 1 calc R U . . .
C4 C 0.9702(5) 0.7848(3) 0.09872(13) 0.0481(6) Uani 1 1 d . . . . .
H4 H 0.945479 0.814086 0.047436 0.058 Uiso 1 1 calc R U . . .
C5 C 0.8156(5) 0.6852(3) 0.14115(14) 0.0430(6) Uani 1 1 d . . . . .
H5 H 0.685890 0.646271 0.118939 0.052 Uiso 1 1 calc R U . . .
C6 C 0.8512(4) 0.6428(3) 0.21593(12) 0.0346(5) Uani 1 1 d . . . . .
H6 H 0.746003 0.575322 0.245523 0.042 Uiso 1 1 calc R U . . .
S S 1.08625(8) 0.64561(5) 0.34306(3) 0.02381(15) Uani 1 1 d . . . . .
O1 O 1.3188(2) 0.69003(19) 0.35937(9) 0.0343(4) Uani 1 1 d . . . . .
O2 O 1.0268(3) 0.48457(16) 0.36313(8) 0.0304(3) Uani 1 1 d . . . . .
C7 C 0.8733(3) 0.7636(2) 0.38220(11) 0.0235(4) Uani 1 1 d . . . . .
H7A H 0.915919 0.874458 0.369472 0.028 Uiso 1 1 calc R U . . .
H7B H 0.718552 0.752059 0.360665 0.028 Uiso 1 1 calc R U . . .
C8 C 0.8524(3) 0.7211(2) 0.46581(11) 0.0254(4) Uani 1 1 d . . . . .
H8A H 1.008721 0.723602 0.487820 0.031 Uiso 1 1 calc R U . . .
H8B H 0.792259 0.614360 0.479229 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6831(3) 0.8392(2) 0.49486(11) 0.0253(4) Uani 1 1 d . . . . .
H9A H 0.758010 0.941939 0.488375 0.030 Uiso 1 1 calc R U . . .
H9B H 0.539535 0.850906 0.465062 0.030 Uiso 1 1 calc R U . . .
N N 0.6155(3) 0.79516(18) 0.57234(9) 0.0235(3) Uani 1 1 d . . . . .
C10 C 0.4238(3) 0.6860(2) 0.58834(12) 0.0277(4) Uani 1 1 d . . . . .
H10A H 0.272486 0.743763 0.582945 0.042 Uiso 1 1 calc R U . . .
H10B H 0.436108 0.630771 0.638932 0.042 Uiso 1 1 calc R U . . .
H10C H 0.434400 0.610202 0.553873 0.042 Uiso 1 1 calc R U . . .
O3 O 0.9344(2) 0.90803(16) 0.60994(8) 0.0291(3) Uani 1 1 d . . . . .
C11 C 0.7473(3) 0.8390(2) 0.62437(11) 0.0234(4) Uani 1 1 d . . . . .
C12 C 0.6571(3) 0.8097(2) 0.70269(11) 0.0246(4) Uani 1 1 d . . . . .
C13 C 0.8003(4) 0.7318(3) 0.75755(12) 0.0310(4) Uani 1 1 d . . . . .
H13 H 0.950936 0.691727 0.744692 0.037 Uiso 1 1 calc R U . . .
C14 C 0.7257(4) 0.7121(3) 0.83071(12) 0.0360(5) Uani 1 1 d . . . . .
H14 H 0.822327 0.655783 0.867740 0.043 Uiso 1 1 calc R U . . .
C15 C 0.5086(4) 0.7753(3) 0.84969(12) 0.0326(5) Uani 1 1 d . . . . .
C18 C 0.4246(5) 0.7569(3) 0.92859(13) 0.0413(5) Uani 1 1 d . . . . .
F1A F 0.2416(4) 0.6687(3) 0.94186(10) 0.0730(9) Uani 0.890(5) 1 d . . P A 1
F2A F 0.3653(8) 0.8907(3) 0.94982(13) 0.1005(14) Uani 0.890(5) 1 d . . P A 1
F3A F 0.5852(4) 0.6919(5) 0.97545(10) 0.1013(13) Uani 0.890(5) 1 d . . P A 1
F1B F 0.188(3) 0.796(2) 0.9343(9) 0.058(5) Uiso 0.110(5) 1 d . . P A 2
F2B F 0.510(3) 0.838(2) 0.9655(8) 0.046(4) Uiso 0.110(5) 1 d . . P A 2
F3B F 0.448(3) 0.6164(18) 0.9623(9) 0.058(5) Uiso 0.110(5) 1 d . . P A 2
C16 C 0.3655(4) 0.8557(3) 0.79562(12) 0.0335(5) Uani 1 1 d . . . . .
H16 H 0.218707 0.900675 0.808864 0.040 Uiso 1 1 calc R U . . .
C17 C 0.4377(4) 0.8702(2) 0.72245(12) 0.0295(4) Uani 1 1 d . . . . .
H17 H 0.337184 0.921631 0.685275 0.035 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
C1 C2 1.383(3) . ?
C1 C6 1.391(3) . ?
C1 S 1.773(2) . ?
C2 C3 1.393(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
S O2 1.4369(15) . ?
S O1 1.4431(15) . ?
S C7 1.7661(19) . ?
C7 C8 1.525(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.526(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N 1.459(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N C11 1.340(2) . ?
N C10 1.462(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O3 C11 1.241(2) . ?
C11 C12 1.500(3) . ?
C12 C13 1.390(3) . ?
C12 C17 1.396(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 C18 1.499(3) . ?
C18 F2B 1.174(16) . ?
C18 F3B 1.282(16) . ?
C18 F1A 1.308(3) . ?
C18 F2A 1.310(3) . ?
C18 F3A 1.324(3) . ?
C18 F1B 1.379(17) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
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
C2 C1 C6 121.6(2) . . ?
C2 C1 S 119.77(17) . . ?
C6 C1 S 118.67(16) . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O2 S O1 118.07(9) . . ?
O2 S C7 108.94(9) . . ?
O1 S C7 109.54(9) . . ?
O2 S C1 108.24(9) . . ?
O1 S C1 108.33(10) . . ?
C7 S C1 102.59(9) . . ?
C8 C7 S 112.45(13) . . ?
C8 C7 H7A 109.1 . . ?
S C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
S C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 108.38(15) . . ?
C7 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N C9 C8 113.47(16) . . ?
N C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
N C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 N C9 119.42(16) . . ?
C11 N C10 123.57(17) . . ?
C9 N C10 116.44(16) . . ?
N C10 H10A 109.5 . . ?
N C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 N 122.75(18) . . ?
O3 C11 C12 119.10(17) . . ?
N C11 C12 118.08(17) . . ?
C13 C12 C17 119.09(19) . . ?
C13 C12 C11 119.82(18) . . ?
C17 C12 C11 120.90(18) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 C18 119.0(2) . . ?
C14 C15 C18 120.7(2) . . ?
F2B C18 F3B 106.9(11) . . ?
F1A C18 F2A 106.7(3) . . ?
F1A C18 F3A 105.3(3) . . ?
F2A C18 F3A 105.3(3) . . ?
F2B C18 F1B 102.4(11) . . ?
F3B C18 F1B 105.5(11) . . ?
F2B C18 C15 116.3(8) . . ?
F3B C18 C15 113.2(8) . . ?
F1A C18 C15 113.0(2) . . ?
F2A C18 C15 112.6(2) . . ?
F3A C18 C15 113.3(2) . . ?
F1B C18 C15 111.5(7) . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C12 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.8(3) . . . . ?
S C1 C2 C3 -179.87(19) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
S C1 C6 C5 179.83(18) . . . . ?
C2 C1 S O2 -142.45(17) . . . . ?
C6 C1 S O2 38.48(18) . . . . ?
C2 C1 S O1 -13.3(2) . . . . ?
C6 C1 S O1 167.61(16) . . . . ?
C2 C1 S C7 102.48(18) . . . . ?
C6 C1 S C7 -76.60(18) . . . . ?
O2 S C7 C8 57.43(16) . . . . ?
O1 S C7 C8 -73.09(16) . . . . ?
C1 S C7 C8 171.99(14) . . . . ?
S C7 C8 C9 174.46(13) . . . . ?
C7 C8 C9 N 169.57(15) . . . . ?
C8 C9 N C11 88.6(2) . . . . ?
C8 C9 N C10 -83.0(2) . . . . ?
C9 N C11 O3 -4.5(3) . . . . ?
C10 N C11 O3 166.45(17) . . . . ?
C9 N C11 C12 172.40(16) . . . . ?
C10 N C11 C12 -16.6(3) . . . . ?
O3 C11 C12 C13 -54.9(3) . . . . ?
N C11 C12 C13 128.0(2) . . . . ?
O3 C11 C12 C17 120.1(2) . . . . ?
N C11 C12 C17 -57.0(2) . . . . ?
C17 C12 C13 C14 1.0(3) . . . . ?
C11 C12 C13 C14 176.04(18) . . . . ?
C12 C13 C14 C15 -2.1(3) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C13 C14 C15 C18 -179.4(2) . . . . ?
C16 C15 C18 F2B -103.7(10) . . . . ?
C14 C15 C18 F2B 76.7(10) . . . . ?
C16 C15 C18 F3B 132.0(10) . . . . ?
C14 C15 C18 F3B -47.7(10) . . . . ?
C16 C15 C18 F1A 66.6(3) . . . . ?
C14 C15 C18 F1A -113.0(3) . . . . ?
C16 C15 C18 F2A -54.3(4) . . . . ?
C14 C15 C18 F2A 126.1(3) . . . . ?
C16 C15 C18 F3A -173.7(3) . . . . ?
C14 C15 C18 F3A 6.6(4) . . . . ?
C16 C15 C18 F1B 13.2(9) . . . . ?
C14 C15 C18 F1B -166.4(9) . . . . ?
C14 C15 C16 C17 1.3(3) . . . . ?
C18 C15 C16 C17 -178.3(2) . . . . ?
C15 C16 C17 C12 -2.5(3) . . . . ?
C13 C12 C17 C16 1.3(3) . . . . ?
C11 C12 C17 C16 -173.69(19) . . . . ?

_refine_diff_density_max         0.835
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.063

