# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_18
_database_code_depnum_ccdc_archive 'CCDC 1827462'
_audit_update_record             
;
2018-03-05 deposited with the CCDC.
2018-05-04 downloaded from the CCDC.
;
_audit_creation_date             2017-02-07
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C19 H13 Br F3 N O3 S'
_chemical_formula_moiety         'C19 H13 Br F3 N O3 S'
_chemical_formula_weight         472.28
_chemical_melting_point          ?
_chemical_absolute_configuration 'ad '

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      hexagonal
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
_space_group_IT_number           169
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -Y,+X-Y,1/3+Z
3 -X+Y,-X,2/3+Z
4 -X,-Y,1/2+Z
5 +Y,-X+Y,5/6+Z
6 +X-Y,+X,1/6+Z
#------------------------------------------------------------------------------
_cell_length_a                   16.963(3)
_cell_length_b                   16.963(3)
_cell_length_c                   11.4256(18)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_volume                     2847.2(8)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    6702
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1416.00
_exptl_absorpt_coefficient_mu    2.331
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_T_max  0.792

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            27554
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_min         2.258
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3460
_reflns_number_gt                3073
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0970
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3460
_refine_ls_number_parameters     253
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0601P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.27
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1319 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(5)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br19 Br 0.78436(5) 0.79725(5) 0.04763(7) 0.0365(2) Uani 1 1 d . . . . .
S7 S 0.61209(10) 0.76207(10) 0.81923(14) 0.0230(3) Uani 1 1 d . . . . .
F1 F 0.4010(2) 0.7432(2) 0.5618(3) 0.0320(9) Uani 1 1 d . . . . .
F2 F 0.4258(2) 0.8089(3) 0.3920(4) 0.0371(9) Uani 1 1 d . . . . .
F3 F 0.4664(2) 0.7090(2) 0.4261(3) 0.0312(9) Uani 1 1 d . . . . .
O2 O 0.4840(3) 0.9571(3) 0.7478(4) 0.0358(12) Uani 1 1 d . . . . .
O15 O 0.6711(3) 0.7325(3) 0.6239(4) 0.0280(10) Uani 1 1 d . . . . .
O31 O 0.8765(6) 0.9558(5) 0.6241(8) 0.113(3) Uani 1 1 d . . . . .
N1 N 0.5320(3) 0.8535(3) 0.7634(5) 0.0213(11) Uani 1 1 d . . . . .
C2 C 0.5152(4) 0.9156(4) 0.7016(6) 0.0247(14) Uani 1 1 d . . . . .
C3 C 0.5447(4) 0.9303(4) 0.5741(5) 0.0268(14) Uani 1 1 d . . . . .
H3A H 0.6044 0.9870 0.5689 0.032 Uiso 1 1 calc R U . . .
H3B H 0.5005 0.9402 0.5291 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5532(4) 0.8539(4) 0.5140(5) 0.0225(14) Uani 1 1 d . . . . .
H4 H 0.5929 0.8801 0.4435 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5984(4) 0.8177(4) 0.5961(5) 0.0206(13) Uani 1 1 d . . . . .
C6 C 0.5791(4) 0.8141(4) 0.7138(6) 0.0205(12) Uani 1 1 d . . . . .
C8 C 0.5578(4) 0.7898(4) 0.9290(6) 0.0231(14) Uani 1 1 d . . . . .
C9 C 0.5522(4) 0.7669(4) 1.0461(6) 0.0292(14) Uani 1 1 d . . . . .
H9 H 0.5802 0.7342 1.0746 0.035 Uiso 1 1 calc R U . . .
C10 C 0.5041(4) 0.7930(4) 1.1218(6) 0.0324(16) Uani 1 1 d . . . . .
H10 H 0.4999 0.7787 1.2028 0.039 Uiso 1 1 calc R U . . .
C11 C 0.4629(4) 0.8396(5) 1.0784(6) 0.0316(16) Uani 1 1 d . . . . .
H11 H 0.4302 0.8564 1.1307 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4676(4) 0.8626(4) 0.9610(6) 0.0289(15) Uani 1 1 d . . . . .
H12 H 0.4382 0.8939 0.9324 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5169(4) 0.8380(4) 0.8866(6) 0.0247(13) Uani 1 1 d . . . . .
C14 C 0.4624(4) 0.7787(4) 0.4745(6) 0.0277(15) Uani 1 1 d . . . . .
C15 C 0.6504(4) 0.7759(4) 0.5557(6) 0.0242(13) Uani 1 1 d . . . . .
C16 C 0.6792(4) 0.7827(4) 0.4301(5) 0.0226(13) Uani 1 1 d . . . . .
C17 C 0.7301(4) 0.8674(4) 0.3739(6) 0.0239(13) Uani 1 1 d . . . . .
H17 H 0.7423 0.9216 0.4134 0.029 Uiso 1 1 calc R U . . .
C18 C 0.7628(4) 0.8721(4) 0.2608(6) 0.0264(14) Uani 1 1 d . . . . .
H18 H 0.7979 0.9293 0.2231 0.032 Uiso 1 1 calc R U . . .
C19 C 0.7428(4) 0.7913(4) 0.2038(6) 0.0269(14) Uani 1 1 d . . . . .
C20 C 0.6925(4) 0.7070(4) 0.2578(5) 0.0233(13) Uani 1 1 d . . . . .
H20 H 0.6793 0.6528 0.2174 0.028 Uiso 1 1 calc R U . . .
C21 C 0.6616(4) 0.7029(4) 0.3716(6) 0.0223(13) Uani 1 1 d . . . . .
H21 H 0.6284 0.6457 0.4099 0.027 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br19 C19 1.903(7) . ?
S7 C6 1.742(6) . ?
S7 C8 1.754(6) . ?
F1 C14 1.347(7) . ?
F2 C14 1.361(7) . ?
F3 C14 1.337(7) . ?
O2 C2 1.194(7) . ?
O15 C15 1.237(7) . ?
N1 C6 1.393(7) . ?
N1 C2 1.411(8) . ?
N1 C13 1.430(9) . ?
C2 C3 1.519(9) . ?
C3 C4 1.535(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C14 1.497(9) . ?
C4 C5 1.521(8) . ?
C4 H4 1.0000 . ?
C5 C6 1.379(9) . ?
C5 C15 1.457(8) . ?
C8 C9 1.383(10) . ?
C8 C13 1.397(9) . ?
C9 C10 1.405(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(9) . ?
C12 H12 0.9500 . ?
C15 C16 1.501(9) . ?
C16 C21 1.402(9) . ?
C16 C17 1.407(8) . ?
C17 C18 1.392(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.399(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(9) . ?
C20 C21 1.391(9) . ?
C20 H20 0.9500 . ?
C21 H21 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
C6 S7 C8 90.8(3) . . ?
C6 N1 C2 122.2(5) . . ?
C6 N1 C13 113.9(5) . . ?
C2 N1 C13 123.0(5) . . ?
O2 C2 N1 122.2(6) . . ?
O2 C2 C3 122.2(6) . . ?
N1 C2 C3 115.5(5) . . ?
C2 C3 C4 116.9(5) . . ?
C2 C3 H3A 108.1 . . ?
C4 C3 H3A 108.1 . . ?
C2 C3 H3B 108.1 . . ?
C4 C3 H3B 108.1 . . ?
H3A C3 H3B 107.3 . . ?
C14 C4 C5 110.7(5) . . ?
C14 C4 C3 111.3(5) . . ?
C5 C4 C3 110.2(5) . . ?
C14 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C3 C4 H4 108.2 . . ?
C6 C5 C15 118.4(5) . . ?
C6 C5 C4 117.6(5) . . ?
C15 C5 C4 123.5(6) . . ?
C5 C6 N1 123.8(6) . . ?
C5 C6 S7 124.6(4) . . ?
N1 C6 S7 111.6(5) . . ?
C9 C8 C13 121.1(6) . . ?
C9 C8 S7 126.0(5) . . ?
C13 C8 S7 112.9(5) . . ?
C8 C9 C10 118.4(6) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 120.0(7) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 122.2(6) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C13 117.7(6) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C12 C13 C8 120.7(6) . . ?
C12 C13 N1 128.6(6) . . ?
C8 C13 N1 110.7(5) . . ?
F3 C14 F1 106.3(5) . . ?
F3 C14 F2 106.3(5) . . ?
F1 C14 F2 106.6(5) . . ?
F3 C14 C4 113.1(5) . . ?
F1 C14 C4 113.2(5) . . ?
F2 C14 C4 110.9(5) . . ?
O15 C15 C5 120.8(6) . . ?
O15 C15 C16 118.0(5) . . ?
C5 C15 C16 121.2(5) . . ?
C21 C16 C17 119.6(6) . . ?
C21 C16 C15 118.5(5) . . ?
C17 C16 C15 121.7(5) . . ?
C18 C17 C16 120.4(6) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 118.7(6) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C20 C19 C18 121.7(6) . . ?
C20 C19 Br19 119.5(5) . . ?
C18 C19 Br19 118.9(5) . . ?
C19 C20 C21 119.3(6) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C20 C21 C16 120.3(6) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 O2 -171.5(5) . . . . ?
C13 N1 C2 O2 -2.7(9) . . . . ?
C6 N1 C2 C3 5.0(8) . . . . ?
C13 N1 C2 C3 173.8(5) . . . . ?
O2 C2 C3 C4 -160.2(6) . . . . ?
N1 C2 C3 C4 23.3(7) . . . . ?
C2 C3 C4 C14 81.1(7) . . . . ?
C2 C3 C4 C5 -42.0(7) . . . . ?
C14 C4 C5 C6 -88.1(7) . . . . ?
C3 C4 C5 C6 35.4(7) . . . . ?
C14 C4 C5 C15 83.4(7) . . . . ?
C3 C4 C5 C15 -153.1(5) . . . . ?
C15 C5 C6 N1 178.3(5) . . . . ?
C4 C5 C6 N1 -9.8(8) . . . . ?
C15 C5 C6 S7 -0.4(8) . . . . ?
C4 C5 C6 S7 171.6(4) . . . . ?
C2 N1 C6 C5 -12.6(8) . . . . ?
C13 N1 C6 C5 177.7(5) . . . . ?
C2 N1 C6 S7 166.2(4) . . . . ?
C13 N1 C6 S7 -3.5(6) . . . . ?
C8 S7 C6 C5 -178.8(5) . . . . ?
C8 S7 C6 N1 2.4(4) . . . . ?
C6 S7 C8 C9 178.2(6) . . . . ?
C6 S7 C8 C13 -0.7(5) . . . . ?
C13 C8 C9 C10 0.2(9) . . . . ?
S7 C8 C9 C10 -178.6(5) . . . . ?
C8 C9 C10 C11 0.7(9) . . . . ?
C9 C10 C11 C12 -0.4(10) . . . . ?
C10 C11 C12 C13 -0.8(10) . . . . ?
C11 C12 C13 C8 1.7(9) . . . . ?
C11 C12 C13 N1 -180.0(6) . . . . ?
C9 C8 C13 C12 -1.4(9) . . . . ?
S7 C8 C13 C12 177.5(5) . . . . ?
C9 C8 C13 N1 180.0(5) . . . . ?
S7 C8 C13 N1 -1.1(6) . . . . ?
C6 N1 C13 C12 -175.5(6) . . . . ?
C2 N1 C13 C12 14.9(9) . . . . ?
C6 N1 C13 C8 3.0(7) . . . . ?
C2 N1 C13 C8 -166.7(5) . . . . ?
C5 C4 C14 F3 -54.5(7) . . . . ?
C3 C4 C14 F3 -177.3(5) . . . . ?
C5 C4 C14 F1 66.4(7) . . . . ?
C3 C4 C14 F1 -56.4(7) . . . . ?
C5 C4 C14 F2 -173.8(5) . . . . ?
C3 C4 C14 F2 63.4(7) . . . . ?
C6 C5 C15 O15 5.2(9) . . . . ?
C4 C5 C15 O15 -166.3(6) . . . . ?
C6 C5 C15 C16 -175.9(5) . . . . ?
C4 C5 C15 C16 12.7(9) . . . . ?
O15 C15 C16 C21 48.7(8) . . . . ?
C5 C15 C16 C21 -130.3(6) . . . . ?
O15 C15 C16 C17 -125.5(6) . . . . ?
C5 C15 C16 C17 55.5(8) . . . . ?
C21 C16 C17 C18 0.1(9) . . . . ?
C15 C16 C17 C18 174.3(6) . . . . ?
C16 C17 C18 C19 0.9(9) . . . . ?
C17 C18 C19 C20 -0.8(9) . . . . ?
C17 C18 C19 Br19 178.2(5) . . . . ?
C18 C19 C20 C21 -0.4(9) . . . . ?
Br19 C19 C20 C21 -179.4(4) . . . . ?
C19 C20 C21 C16 1.5(9) . . . . ?
C17 C16 C21 C20 -1.4(9) . . . . ?
C15 C16 C21 C20 -175.7(5) . . . . ?

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

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


