# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_YYB0370
_audit_block_doi                 10.5517/ccdc.csd.cc1p2cvz
_database_code_depnum_ccdc_archive 'CCDC 1551421'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H28 F3 N O4 S'
_chemical_formula_weight         627.65

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'
S S 0.1246 0.1234 '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'
F F 0.0171 0.0103 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4929(4)
_cell_length_b                   10.5985(5)
_cell_length_c                   30.6529(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.628(2)
_cell_angle_gamma                90
_cell_volume                     3074.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    504
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6969
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43778
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.034
_diffrn_reflns_theta_max         25.248
_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             5568
_reflns_number_gt                4582
_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 KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0627P)²+1.3181P] 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_number_reflns         5568
_refine_ls_number_parameters     434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.003
_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
N1 N 0.76658(18) 0.44751(16) 0.16518(5) 0.0470(4) Uani 1 1 d . . . . .
S1 S 0.78771(5) 0.39677(5) 0.21738(2) 0.04585(16) Uani 1 1 d . . . . .
O1 O 1.04096(18) -0.09658(15) 0.11627(7) 0.0712(5) Uani 1 1 d . . . . .
O2 O 0.85898(15) 0.27946(15) 0.21658(5) 0.0576(4) Uani 1 1 d . . . . .
O3 O 0.84876(16) 0.49888(15) 0.24214(5) 0.0593(4) Uani 1 1 d . . . . .
O4 O 0.48862(18) 0.86968(15) 0.09748(5) 0.0641(4) Uani 1 1 d . . . . .
C1 C 1.0661(2) -0.3168(2) 0.11969(8) 0.0560(5) Uani 1 1 d . . . . .
C2 C 1.1407(4) -0.3505(3) 0.08510(10) 0.0867(9) Uani 1 1 d . . . . .
H2B H 1.1213 -0.3109 0.0582 0.104 Uiso 1 1 calc R U . . .
C3 C 1.2435(4) -0.4414(3) 0.08940(13) 0.0979(10) Uani 1 1 d . . . . .
H3B H 1.2933 -0.4621 0.0655 0.118 Uiso 1 1 calc R U . . .
C4 C 1.2731(3) -0.5004(3) 0.12731(14) 0.0901(10) Uani 1 1 d . . . . .
H4A H 1.3444 -0.5607 0.1302 0.108 Uiso 1 1 calc R U . . .
C5 C 1.1977(4) -0.4715(3) 0.16180(12) 0.1008(11) Uani 1 1 d . . . . .
H5A H 1.2170 -0.5130 0.1883 0.121 Uiso 1 1 calc R U . . .
C6 C 1.0920(4) -0.3804(3) 0.15786(9) 0.0791(8) Uani 1 1 d . . . . .
H6A H 1.0391 -0.3631 0.1814 0.095 Uiso 1 1 calc R U . . .
C7 C 0.9613(3) -0.2113(2) 0.11641(10) 0.0702(7) Uani 1 1 d . . . . .
H7A H 0.8997 -0.2187 0.0897 0.084 Uiso 1 1 calc R U . . .
H7B H 0.9037 -0.2129 0.1411 0.084 Uiso 1 1 calc R U . . .
C8 C 0.9701(2) 0.0148(2) 0.11889(8) 0.0556(5) Uani 1 1 d . . . . .
C9 C 0.8264(3) 0.0264(2) 0.11998(9) 0.0662(7) Uani 1 1 d . . . . .
H9A H 0.7693 -0.0451 0.1184 0.079 Uiso 1 1 calc R U . . .
C10 C 0.7668(2) 0.1447(2) 0.12338(9) 0.0630(6) Uani 1 1 d . . . . .
H10A H 0.6694 0.1518 0.1242 0.076 Uiso 1 1 calc R U . . .
C11 C 0.8484(2) 0.25170(19) 0.12564(7) 0.0475(5) Uani 1 1 d . . . . .
C12 C 0.9925(3) 0.2386(2) 0.12439(10) 0.0682(7) Uani 1 1 d . . . . .
H12A H 1.0497 0.3100 0.1257 0.082 Uiso 1 1 calc R U . . .
C13 C 1.0528(3) 0.1213(2) 0.12117(10) 0.0730(8) Uani 1 1 d . . . . .
H13A H 1.1503 0.1140 0.1205 0.088 Uiso 1 1 calc R U . . .
C14 C 0.7815(2) 0.37762(19) 0.12680(6) 0.0456(5) Uani 1 1 d . . . . .
C15 C 0.7281(2) 0.4485(2) 0.09243(7) 0.0494(5) Uani 1 1 d . . . . .
C16 C 0.7338(4) 0.4171(2) 0.04550(8) 0.0691(7) Uani 1 1 d . . . . .
C17 C 0.6722(2) 0.56457(19) 0.10823(6) 0.0440(4) Uani 1 1 d . . . . .
C18 C 0.6032(2) 0.6680(2) 0.08755(7) 0.0498(5) Uani 1 1 d . . . . .
H18A H 0.5871 0.6712 0.0572 0.060 Uiso 1 1 calc R U . . .
C19 C 0.5602(2) 0.7645(2) 0.11319(7) 0.0493(5) Uani 1 1 d . . . . .
C20 C 0.5890(2) 0.7612(2) 0.15871(7) 0.0534(5) Uani 1 1 d . . . . .
H20A H 0.5607 0.8286 0.1754 0.064 Uiso 1 1 calc R U . . .
C21 C 0.6577(2) 0.6616(2) 0.17931(7) 0.0530(5) Uani 1 1 d . . . . .
H21A H 0.6770 0.6606 0.2095 0.064 Uiso 1 1 calc R U . . .
C22 C 0.6978(2) 0.56212(19) 0.15360(6) 0.0436(4) Uani 1 1 d . . . . .
C23 C 0.6145(2) 0.3740(2) 0.23195(7) 0.0497(5) Uani 1 1 d . . . . .
C24 C 0.5565(2) 0.4562(3) 0.25998(8) 0.0639(6) Uani 1 1 d . . . . .
H24A H 0.6077 0.5251 0.2714 0.077 Uiso 1 1 calc R U . . .
C25 C 0.4194(3) 0.4344(3) 0.27103(10) 0.0843(9) Uani 1 1 d . . . . .
H25A H 0.3795 0.4896 0.2901 0.101 Uiso 1 1 calc R U . . .
C26 C 0.3416(3) 0.3342(4) 0.25464(12) 0.0901(10) Uani 1 1 d . . . . .
C27 C 0.4026(3) 0.2534(3) 0.22699(12) 0.0910(10) Uani 1 1 d . . . . .
H27A H 0.3508 0.1848 0.2155 0.109 Uiso 1 1 calc R U . . .
C28 C 0.5395(3) 0.2707(3) 0.21553(9) 0.0699(7) Uani 1 1 d . . . . .
H28A H 0.5800 0.2138 0.1971 0.084 Uiso 1 1 calc R U . . .
C29 C 0.1921(3) 0.3129(5) 0.26752(17) 0.148(2) Uani 1 1 d . . . . .
H29A H 0.1533 0.2388 0.2531 0.221 Uiso 1 1 calc R U . . .
H29B H 0.1940 0.3019 0.2986 0.221 Uiso 1 1 calc R U . . .
H29C H 0.1346 0.3847 0.2589 0.221 Uiso 1 1 calc R U . . .
C30 C 0.4462(3) 0.8736(3) 0.05199(8) 0.0725(7) Uani 1 1 d . . . . .
H30A H 0.3901 0.7996 0.0438 0.087 Uiso 1 1 calc R U . . .
H30B H 0.5289 0.8735 0.0354 0.087 Uiso 1 1 calc R U . . .
C31 C 0.3608(3) 0.9904(2) 0.04171(8) 0.0622(6) Uani 1 1 d . . . . .
C32 C 0.2408(3) 0.9865(3) 0.01491(11) 0.0862(9) Uani 1 1 d . . . . .
H32A H 0.2081 0.9091 0.0040 0.103 Uiso 1 1 calc R U . . .
C33 C 0.1659(4) 1.0936(4) 0.00335(13) 0.1017(11) Uani 1 1 d . . . . .
H33A H 0.0841 1.0878 -0.0154 0.122 Uiso 1 1 calc R U . . .
C34 C 0.2093(4) 1.2064(3) 0.01874(12) 0.0909(10) Uani 1 1 d . . . . .
H34A H 0.1569 1.2785 0.0113 0.109 Uiso 1 1 calc R U . . .
C35 C 0.3291(4) 1.2146(3) 0.04503(13) 0.1006(11) Uani 1 1 d . . . . .
H35A H 0.3609 1.2928 0.0555 0.121 Uiso 1 1 calc R U . . .
C36 C 0.4054(4) 1.1065(3) 0.05655(12) 0.0946(10) Uani 1 1 d . . . . .
H36A H 0.4884 1.1130 0.0747 0.114 Uiso 1 1 calc R U . . .
F1 F 0.728(2) 0.2993(7) 0.0372(2) 0.119(5) Uani 0.473(18) 1 d . . P A 1
F2 F 0.8488(10) 0.4658(18) 0.0306(3) 0.137(7) Uani 0.473(18) 1 d . . P A 1
F3 F 0.6292(11) 0.4639(11) 0.02095(17) 0.103(4) Uani 0.473(18) 1 d . . P A 1
F1' F 0.6115(11) 0.375(2) 0.0288(3) 0.183(7) Uani 0.527(18) 1 d . . P A 2
F2' F 0.8211(16) 0.3301(12) 0.0362(2) 0.128(5) Uani 0.527(18) 1 d . . P A 2
F3' F 0.759(2) 0.5104(5) 0.0218(2) 0.151(7) Uani 0.527(18) 1 d . . 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
N1 C14 1.407(3) . ?
N1 C22 1.411(3) . ?
N1 S1 1.6845(16) . ?
S1 O2 1.4166(16) . ?
S1 O3 1.4186(16) . ?
S1 C23 1.755(2) . ?
O1 C8 1.364(3) . ?
O1 C7 1.432(3) . ?
O4 C19 1.373(2) . ?
O4 C30 1.421(3) . ?
C1 C6 1.355(3) . ?
C1 C2 1.369(4) . ?
C1 C7 1.495(3) . ?
C2 C3 1.370(4) . ?
C3 C4 1.329(5) . ?
C4 C5 1.358(5) . ?
C5 C6 1.391(4) . ?
C8 C9 1.373(3) . ?
C8 C13 1.374(3) . ?
C9 C10 1.383(3) . ?
C10 C11 1.373(3) . ?
C11 C12 1.378(3) . ?
C11 C14 1.480(3) . ?
C12 C13 1.375(3) . ?
C14 C15 1.359(3) . ?
C15 C17 1.439(3) . ?
C15 C16 1.482(3) . ?
C16 F3' 1.261(6) . ?
C16 F1 1.274(7) . ?
C16 F2' 1.287(7) . ?
C16 F3 1.295(6) . ?
C16 F1' 1.310(8) . ?
C16 F2 1.322(7) . ?
C17 C22 1.393(3) . ?
C17 C18 1.402(3) . ?
C18 C19 1.372(3) . ?
C19 C20 1.400(3) . ?
C20 C21 1.369(3) . ?
C21 C22 1.387(3) . ?
C23 C24 1.370(3) . ?
C23 C28 1.379(3) . ?
C24 C25 1.390(4) . ?
C25 C26 1.366(5) . ?
C26 C27 1.366(5) . ?
C26 C29 1.520(4) . ?
C27 C28 1.385(4) . ?
C30 C31 1.499(3) . ?
C31 C32 1.350(4) . ?
C31 C36 1.367(4) . ?
C32 C33 1.371(4) . ?
C33 C34 1.338(5) . ?
C34 C35 1.343(5) . ?
C35 C36 1.386(4) . ?

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
C14 N1 C22 108.60(15) . . ?
C14 N1 S1 127.86(14) . . ?
C22 N1 S1 122.07(13) . . ?
O2 S1 O3 120.25(10) . . ?
O2 S1 N1 106.52(9) . . ?
O3 S1 N1 106.07(9) . . ?
O2 S1 C23 110.00(10) . . ?
O3 S1 C23 108.63(10) . . ?
N1 S1 C23 104.09(9) . . ?
C8 O1 C7 118.09(18) . . ?
C19 O4 C30 117.49(18) . . ?
C6 C1 C2 118.0(2) . . ?
C6 C1 C7 120.2(2) . . ?
C2 C1 C7 121.7(2) . . ?
C1 C2 C3 121.2(3) . . ?
C4 C3 C2 120.9(3) . . ?
C3 C4 C5 119.1(3) . . ?
C4 C5 C6 120.7(3) . . ?
C1 C6 C5 119.9(3) . . ?
O1 C7 C1 106.66(19) . . ?
O1 C8 C9 125.1(2) . . ?
O1 C8 C13 115.5(2) . . ?
C9 C8 C13 119.4(2) . . ?
C8 C9 C10 119.8(2) . . ?
C11 C10 C9 121.3(2) . . ?
C10 C11 C12 118.2(2) . . ?
C10 C11 C14 120.32(19) . . ?
C12 C11 C14 121.37(19) . . ?
C13 C12 C11 120.9(2) . . ?
C8 C13 C12 120.4(2) . . ?
C15 C14 N1 107.49(18) . . ?
C15 C14 C11 127.92(19) . . ?
N1 C14 C11 124.57(17) . . ?
C14 C15 C17 109.66(18) . . ?
C14 C15 C16 126.0(2) . . ?
C17 C15 C16 124.22(19) . . ?
F3' C16 F2' 106.1(6) . . ?
F1 C16 F3 104.0(6) . . ?
F3' C16 F1' 104.4(6) . . ?
F2' C16 F1' 103.5(6) . . ?
F1 C16 F2 109.6(6) . . ?
F3 C16 F2 105.4(6) . . ?
F3' C16 C15 113.9(3) . . ?
F1 C16 C15 114.2(5) . . ?
F2' C16 C15 116.8(4) . . ?
F3 C16 C15 113.1(3) . . ?
F1' C16 C15 110.9(4) . . ?
F2 C16 C15 110.1(4) . . ?
C22 C17 C18 120.24(19) . . ?
C22 C17 C15 106.32(17) . . ?
C18 C17 C15 133.43(19) . . ?
C19 C18 C17 118.25(19) . . ?
C18 C19 O4 124.48(19) . . ?
C18 C19 C20 120.63(19) . . ?
O4 C19 C20 114.89(19) . . ?
C21 C20 C19 121.7(2) . . ?
C20 C21 C22 117.81(19) . . ?
C21 C22 C17 121.29(19) . . ?
C21 C22 N1 130.83(18) . . ?
C17 C22 N1 107.88(17) . . ?
C24 C23 C28 120.8(2) . . ?
C24 C23 S1 120.28(18) . . ?
C28 C23 S1 118.90(19) . . ?
C23 C24 C25 118.6(3) . . ?
C26 C25 C24 121.9(3) . . ?
C25 C26 C27 118.2(3) . . ?
C25 C26 C29 120.5(4) . . ?
C27 C26 C29 121.3(4) . . ?
C26 C27 C28 121.8(3) . . ?
C23 C28 C27 118.7(3) . . ?
O4 C30 C31 109.7(2) . . ?
C32 C31 C36 117.0(2) . . ?
C32 C31 C30 121.2(2) . . ?
C36 C31 C30 121.7(2) . . ?
C31 C32 C33 121.8(3) . . ?
C34 C33 C32 120.7(3) . . ?
C33 C34 C35 119.4(3) . . ?
C34 C35 C36 119.9(3) . . ?
C31 C36 C35 121.2(3) . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.042

_shelxl_version_number           2014/6



