# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_shelxl
_audit_block_doi                 10.5517/ccdc.csd.cc21bmrs
_database_code_depnum_ccdc_archive 'CCDC 1887055'
_audit_update_record             
;
2018-12-23 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 F3 N O4 S'
_chemical_formula_weight         373.34

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'
S S 0.3331 0.5567 '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'

_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                   7.91930(10)
_cell_length_b                   15.3744(2)
_cell_length_c                   16.4929(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2008.08(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    5287
_cell_measurement_theta_min      5.3450
_cell_measurement_theta_max      70.9610

_exptl_crystal_description       blcok
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.853
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.697
_exptl_absorpt_correction_T_min  0.66893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(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, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            6685
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.931
_diffrn_reflns_theta_max         71.101
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3761
_reflns_number_gt                3655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.947
_reflns_Friedel_fraction_full    0.988

_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 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_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)+(0.0796P)²+0.0962P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1500 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.001(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3761
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.08615(8) 0.47466(5) 0.27748(5) 0.0694(3) Uani 1 1 d . . . . .
O4 O 0.4299(2) 0.31690(11) 0.24365(12) 0.0550(4) Uani 1 1 d . . . . .
F3 F 0.4332(3) 0.40544(17) 0.09747(10) 0.0941(7) Uani 1 1 d . . . . .
F1 F 0.6216(3) 0.45235(19) 0.17948(12) 0.0940(7) Uani 1 1 d . . . . .
F2 F 0.4030(4) 0.52740(14) 0.15622(15) 0.0992(7) Uani 1 1 d . . . . .
N1 N 0.1848(2) 0.39580(12) 0.22542(12) 0.0464(4) Uani 1 1 d . . . . .
O2 O -0.0559(3) 0.4383(2) 0.3174(2) 0.1049(11) Uani 1 1 d . . . . .
C3 C 0.1396(3) 0.30466(15) 0.24975(14) 0.0490(5) Uani 1 1 d . . . . .
H3 H 0.1275 0.3013 0.3088 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3689(3) 0.40273(14) 0.23899(13) 0.0448(5) Uani 1 1 d . . . . .
O3 O 0.0589(4) 0.54714(17) 0.2259(2) 0.1060(11) Uani 1 1 d . . . . .
C8 C 0.3973(3) 0.45317(14) 0.31702(13) 0.0445(4) Uani 1 1 d . . . . .
C9 C 0.2531(3) 0.49479(18) 0.34358(19) 0.0585(6) Uani 1 1 d . . . . .
C4 C 0.2952(4) 0.25619(15) 0.22371(16) 0.0552(6) Uani 1 1 d . . . . .
C13 C 0.5437(3) 0.45905(18) 0.36168(16) 0.0531(5) Uani 1 1 d . . . . .
H13 H 0.6418 0.4322 0.3434 0.064 Uiso 1 1 calc R U . . .
O1 O -0.1269(5) 0.2700(3) 0.0750(2) 0.1207(12) Uani 1 1 d . . . . .
C16 C 0.4576(4) 0.4471(2) 0.16672(17) 0.0662(7) Uani 1 1 d . . . . .
C2 C -0.0211(4) 0.2729(2) 0.20925(19) 0.0654(7) Uani 1 1 d . . . . .
H2A H -0.0525 0.2174 0.2328 0.079 Uiso 1 1 calc R U . . .
H2B H -0.1112 0.3138 0.2207 0.079 Uiso 1 1 calc R U . . .
C5 C 0.2959(5) 0.2377(2) 0.13347(19) 0.0740(9) Uani 1 1 d . . . . .
H5 H 0.3984 0.2240 0.1091 0.089 Uiso 1 1 calc R U . . .
C1 C -0.0063(5) 0.2623(2) 0.1196(2) 0.0750(9) Uani 1 1 d . . . . .
C10 C 0.2507(4) 0.5427(2) 0.4145(2) 0.0788(9) Uani 1 1 d . . . . .
H10 H 0.1532 0.5709 0.4317 0.095 Uiso 1 1 calc R U . . .
C12 C 0.5448(4) 0.5053(2) 0.43425(18) 0.0632(7) Uani 1 1 d . . . . .
C6 C 0.1607(6) 0.2399(2) 0.0879(2) 0.0802(10) Uani 1 1 d . . . . .
H6 H 0.1712 0.2267 0.0331 0.096 Uiso 1 1 calc R U . . .
C11 C 0.3981(5) 0.5471(2) 0.4589(2) 0.0800(9) Uani 1 1 d . . . . .
H11 H 0.3993 0.5791 0.5068 0.096 Uiso 1 1 calc R U . . .
C15 C 0.3302(6) 0.1737(2) 0.2709(3) 0.0942(13) Uani 1 1 d . . . . .
H15A H 0.4417 0.1532 0.2584 0.141 Uiso 1 1 calc R U . . .
H15B H 0.2490 0.1301 0.2562 0.141 Uiso 1 1 calc R U . . .
H15C H 0.3221 0.1855 0.3279 0.141 Uiso 1 1 calc R U . . .
C14 C 0.7017(6) 0.5101(3) 0.4853(2) 0.0925(11) Uani 1 1 d . . . . .
H14A H 0.7224 0.4545 0.5098 0.139 Uiso 1 1 calc R U . . .
H14B H 0.6869 0.5531 0.5269 0.139 Uiso 1 1 calc R U . . .
H14C H 0.7961 0.5258 0.4518 0.139 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 1.418(3) . ?
S1 O3 1.419(3) . ?
S1 N1 1.678(2) . ?
S1 C9 1.741(3) . ?
O4 C7 1.407(3) . ?
O4 C4 1.456(3) . ?
F3 C16 1.323(4) . ?
F1 C16 1.319(4) . ?
F2 C16 1.320(4) . ?
N1 C7 1.479(3) . ?
N1 C3 1.501(3) . ?
C3 C4 1.502(4) . ?
C3 C2 1.518(3) . ?
C3 H3 0.9800 . ?
C7 C8 1.519(3) . ?
C7 C16 1.542(4) . ?
C8 C13 1.376(3) . ?
C8 C9 1.381(3) . ?
C9 C10 1.382(4) . ?
C4 C15 1.513(4) . ?
C4 C5 1.515(4) . ?
C13 C12 1.392(4) . ?
C13 H13 0.9300 . ?
O1 C1 1.210(5) . ?
C2 C1 1.492(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C6 1.308(5) . ?
C5 H5 0.9300 . ?
C1 C6 1.463(6) . ?
C10 C11 1.380(5) . ?
C10 H10 0.9300 . ?
C12 C11 1.389(5) . ?
C12 C14 1.503(4) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 117.9(2) . . ?
O2 S1 N1 108.76(14) . . ?
O3 S1 N1 109.35(17) . . ?
O2 S1 C9 112.45(17) . . ?
O3 S1 C9 110.58(17) . . ?
N1 S1 C9 95.48(11) . . ?
C7 O4 C4 109.69(17) . . ?
C7 N1 C3 105.17(17) . . ?
C7 N1 S1 109.22(14) . . ?
C3 N1 S1 115.26(16) . . ?
N1 C3 C4 101.02(18) . . ?
N1 C3 C2 112.5(2) . . ?
C4 C3 C2 113.7(2) . . ?
N1 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
O4 C7 N1 106.22(18) . . ?
O4 C7 C8 112.41(19) . . ?
N1 C7 C8 108.13(18) . . ?
O4 C7 C16 107.5(2) . . ?
N1 C7 C16 111.3(2) . . ?
C8 C7 C16 111.2(2) . . ?
C13 C8 C9 119.8(2) . . ?
C13 C8 C7 127.7(2) . . ?
C9 C8 C7 112.5(2) . . ?
C8 C9 C10 121.8(3) . . ?
C8 C9 S1 110.31(19) . . ?
C10 C9 S1 127.9(2) . . ?
O4 C4 C3 102.63(17) . . ?
O4 C4 C15 106.7(2) . . ?
C3 C4 C15 114.8(3) . . ?
O4 C4 C5 109.8(2) . . ?
C3 C4 C5 112.2(2) . . ?
C15 C4 C5 110.3(3) . . ?
C8 C13 C12 119.9(2) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
F1 C16 F2 106.6(3) . . ?
F1 C16 F3 108.1(3) . . ?
F2 C16 F3 107.0(3) . . ?
F1 C16 C7 110.6(2) . . ?
F2 C16 C7 111.5(3) . . ?
F3 C16 C7 112.7(2) . . ?
C1 C2 C3 113.9(3) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C6 C5 C4 123.7(3) . . ?
C6 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
O1 C1 C6 121.3(4) . . ?
O1 C1 C2 121.9(4) . . ?
C6 C1 C2 116.8(3) . . ?
C11 C10 C9 117.7(3) . . ?
C11 C10 H10 121.2 . . ?
C9 C10 H10 121.2 . . ?
C11 C12 C13 118.9(3) . . ?
C11 C12 C14 120.3(3) . . ?
C13 C12 C14 120.8(3) . . ?
C5 C6 C1 122.8(3) . . ?
C5 C6 H6 118.6 . . ?
C1 C6 H6 118.6 . . ?
C10 C11 C12 121.9(3) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 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
O2 S1 N1 C7 -135.2(2) . . . . ?
O3 S1 N1 C7 94.8(2) . . . . ?
C9 S1 N1 C7 -19.2(2) . . . . ?
O2 S1 N1 C3 -17.1(2) . . . . ?
O3 S1 N1 C3 -147.1(2) . . . . ?
C9 S1 N1 C3 98.87(19) . . . . ?
C7 N1 C3 C4 -34.6(2) . . . . ?
S1 N1 C3 C4 -154.98(15) . . . . ?
C7 N1 C3 C2 -156.2(2) . . . . ?
S1 N1 C3 C2 83.4(2) . . . . ?
C4 O4 C7 N1 6.9(2) . . . . ?
C4 O4 C7 C8 125.0(2) . . . . ?
C4 O4 C7 C16 -112.4(2) . . . . ?
C3 N1 C7 O4 18.0(2) . . . . ?
S1 N1 C7 O4 142.28(15) . . . . ?
C3 N1 C7 C8 -102.9(2) . . . . ?
S1 N1 C7 C8 21.4(2) . . . . ?
C3 N1 C7 C16 134.7(2) . . . . ?
S1 N1 C7 C16 -101.0(2) . . . . ?
O4 C7 C8 C13 47.9(3) . . . . ?
N1 C7 C8 C13 164.8(2) . . . . ?
C16 C7 C8 C13 -72.7(3) . . . . ?
O4 C7 C8 C9 -130.6(2) . . . . ?
N1 C7 C8 C9 -13.6(3) . . . . ?
C16 C7 C8 C9 108.9(3) . . . . ?
C13 C8 C9 C10 -0.1(4) . . . . ?
C7 C8 C9 C10 178.5(3) . . . . ?
C13 C8 C9 S1 -178.6(2) . . . . ?
C7 C8 C9 S1 0.0(3) . . . . ?
O2 S1 C9 C8 124.3(2) . . . . ?
O3 S1 C9 C8 -101.7(3) . . . . ?
N1 S1 C9 C8 11.4(2) . . . . ?
O2 S1 C9 C10 -54.1(4) . . . . ?
O3 S1 C9 C10 80.0(4) . . . . ?
N1 S1 C9 C10 -167.0(3) . . . . ?
C7 O4 C4 C3 -28.8(2) . . . . ?
C7 O4 C4 C15 -149.9(3) . . . . ?
C7 O4 C4 C5 90.6(2) . . . . ?
N1 C3 C4 O4 38.0(2) . . . . ?
C2 C3 C4 O4 158.7(2) . . . . ?
N1 C3 C4 C15 153.3(3) . . . . ?
C2 C3 C4 C15 -86.0(3) . . . . ?
N1 C3 C4 C5 -79.8(3) . . . . ?
C2 C3 C4 C5 40.9(3) . . . . ?
C9 C8 C13 C12 1.4(4) . . . . ?
C7 C8 C13 C12 -177.0(2) . . . . ?
O4 C7 C16 F1 -63.7(3) . . . . ?
N1 C7 C16 F1 -179.6(2) . . . . ?
C8 C7 C16 F1 59.7(3) . . . . ?
O4 C7 C16 F2 177.8(2) . . . . ?
N1 C7 C16 F2 61.9(3) . . . . ?
C8 C7 C16 F2 -58.8(3) . . . . ?
O4 C7 C16 F3 57.5(3) . . . . ?
N1 C7 C16 F3 -58.4(3) . . . . ?
C8 C7 C16 F3 -179.0(2) . . . . ?
N1 C3 C2 C1 66.4(3) . . . . ?
C4 C3 C2 C1 -47.6(3) . . . . ?
O4 C4 C5 C6 -132.1(3) . . . . ?
C3 C4 C5 C6 -18.7(4) . . . . ?
C15 C4 C5 C6 110.6(4) . . . . ?
C3 C2 C1 O1 -151.6(3) . . . . ?
C3 C2 C1 C6 30.0(4) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
S1 C9 C10 C11 177.7(3) . . . . ?
C8 C13 C12 C11 -2.0(4) . . . . ?
C8 C13 C12 C14 178.0(3) . . . . ?
C4 C5 C6 C1 1.2(6) . . . . ?
O1 C1 C6 C5 174.6(4) . . . . ?
C2 C1 C6 C5 -7.0(5) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?
C13 C12 C11 C10 1.4(6) . . . . ?
C14 C12 C11 C10 -178.6(4) . . . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.058 0.250 0.500 212.9 54.8
2 0.008 0.750 0.000 212.9 54.5
_platon_squeeze_details          
;
;

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4



