# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_cjh_5452_0ma
_database_code_depnum_ccdc_archive 'CCDC 2334395'
_audit_update_record             
;
2024-02-21 deposited with the CCDC.	2024-12-01 downloaded from the CCDC.
;
_audit_creation_date             2023-09-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 F3 N2 O'
_chemical_formula_sum            'C18 H13 F3 N2 O'
_chemical_formula_weight         330.30
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   16.2399(12)
_cell_length_b                   47.800(4)
_cell_length_c                   8.1006(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6288.2(9)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    294.00
_cell_measurement_theta_max      67.786
_cell_measurement_theta_min      3.699
_shelx_estimated_absorpt_T_max   0.846
_shelx_estimated_absorpt_T_min   0.782
_exptl_absorpt_coefficient_mu    0.959
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1286 before and 0.0683 after correction.
The Ratio of minimum to maximum transmission is 0.8562.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       57
_diffrn_reflns_limit_k_min       -57
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27508
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.742
_diffrn_reflns_theta_min         3.699
_diffrn_ambient_temperature      294.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2729
_reflns_number_total             2873
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1160 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+2.8909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1033
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), N007(H007), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.52042(11) 0.39569(4) 0.3810(3) 0.0515(5) Uani 1 1 d . . . . .
F002 F 0.49616(12) 0.44936(5) 0.5358(3) 0.0791(6) Uani 1 1 d . . . . .
N003 N 0.42615(14) 0.36387(5) 0.4659(3) 0.0484(6) Uani 1 1 d . . . . .
H003 H 0.374751 0.360602 0.482769 0.058 Uiso 1 1 calc R U . . .
F004 F 0.50717(13) 0.45689(5) 0.2782(4) 0.0954(8) Uani 1 1 d . . . . .
F005 F 0.42540(14) 0.48196(4) 0.4238(5) 0.1124(12) Uani 1 1 d . . . . .
C006 C 0.44814(16) 0.38904(6) 0.4031(3) 0.0440(6) Uani 1 1 d . . . . .
N007 N 0.30808(15) 0.44784(5) 0.3341(4) 0.0615(7) Uani 1 1 d . . . . .
H007 H 0.296707 0.465408 0.332061 0.074 Uiso 1 1 calc R U . . .
C008 C 0.29549(17) 0.40110(6) 0.3187(3) 0.0464(6) Uani 1 1 d . . . . .
C009 C 0.37904(16) 0.40790(6) 0.3649(4) 0.0451(6) Uani 1 1 d . . . . .
C00A C 0.38344(16) 0.43662(6) 0.3691(4) 0.0521(7) Uani 1 1 d . . . . .
C00B C 0.51692(18) 0.29683(6) 0.6282(4) 0.0517(7) Uani 1 1 d . . . . .
C00C C 0.48281(16) 0.34304(6) 0.5045(4) 0.0476(6) Uani 1 1 d . . . . .
H00C H 0.537767 0.345754 0.476462 0.057 Uiso 1 1 calc R U . . .
C00D C 0.46156(18) 0.31947(6) 0.5798(4) 0.0520(7) Uani 1 1 d . . . . .
H00D H 0.406007 0.317134 0.604022 0.062 Uiso 1 1 calc R U . . .
C00E C 0.25310(18) 0.42649(6) 0.3024(4) 0.0542(7) Uani 1 1 d . . . . .
C00F C 0.25353(19) 0.37630(7) 0.2825(4) 0.0551(7) Uani 1 1 d . . . . .
H00F H 0.280160 0.359105 0.288284 0.066 Uiso 1 1 calc R U . . .
C00G C 0.1721(2) 0.37795(8) 0.2381(5) 0.0670(9) Uani 1 1 d . . . . .
H00G H 0.143712 0.361577 0.213503 0.080 Uiso 1 1 calc R U . . .
C00H C 0.16984(19) 0.42813(8) 0.2599(5) 0.0670(9) Uani 1 1 d . . . . .
H00H H 0.142618 0.445211 0.253253 0.080 Uiso 1 1 calc R U . . .
C00I C 0.4532(2) 0.45592(7) 0.4018(6) 0.0683(9) Uani 1 1 d . . . . .
C00J C 0.4850(2) 0.27418(6) 0.7159(5) 0.0642(8) Uani 1 1 d . . . . .
H00J H 0.428869 0.273439 0.738008 0.077 Uiso 1 1 calc R U . . .
C00K C 0.6007(2) 0.29670(7) 0.5935(5) 0.0703(10) Uani 1 1 d . . . . .
H00K H 0.623503 0.311305 0.532962 0.084 Uiso 1 1 calc R U . . .
C00L C 0.1305(2) 0.40355(8) 0.2289(5) 0.0705(10) Uani 1 1 d . . . . .
H00L H 0.074940 0.403771 0.200979 0.085 Uiso 1 1 calc R U . . .
C00M C 0.5355(3) 0.25284(7) 0.7705(5) 0.0821(12) Uani 1 1 d . . . . .
H00M H 0.513291 0.238114 0.830969 0.099 Uiso 1 1 calc R U . . .
C00N C 0.6509(3) 0.27506(9) 0.6479(7) 0.0982(15) Uani 1 1 d . . . . .
H00N H 0.706933 0.275388 0.624472 0.118 Uiso 1 1 calc R U . . .
C00O C 0.6184(3) 0.25329(9) 0.7357(6) 0.0950(14) Uani 1 1 d . . . . .
H00O H 0.652190 0.238828 0.771885 0.114 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
O001 C006 1.229(3) . ?
F002 C00I 1.328(5) . ?
N003 H003 0.8600 . ?
N003 C006 1.355(4) . ?
N003 C00C 1.391(3) . ?
F004 C00I 1.331(5) . ?
F005 C00I 1.336(4) . ?
C006 C009 1.472(4) . ?
N007 H007 0.8600 . ?
N007 C00A 1.366(4) . ?
N007 C00E 1.380(4) . ?
C008 C009 1.445(4) . ?
C008 C00E 1.401(4) . ?
C008 C00F 1.399(4) . ?
C009 C00A 1.375(4) . ?
C00A C00I 1.485(4) . ?
C00B C00D 1.461(4) . ?
C00B C00J 1.395(4) . ?
C00B C00K 1.389(4) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.327(4) . ?
C00D H00D 0.9300 . ?
C00E C00H 1.397(4) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.373(4) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.400(5) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.361(5) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.381(5) . ?
C00K H00K 0.9300 . ?
C00K C00N 1.389(5) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00O 1.376(7) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.367(7) . ?
C00O H00O 0.9300 . ?

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
C006 N003 H003 118.5 . . ?
C006 N003 C00C 123.1(2) . . ?
C00C N003 H003 118.5 . . ?
O001 C006 N003 122.4(2) . . ?
O001 C006 C009 122.6(2) . . ?
N003 C006 C009 115.0(2) . . ?
C00A N007 H007 125.4 . . ?
C00A N007 C00E 109.1(2) . . ?
C00E N007 H007 125.4 . . ?
C00E C008 C009 106.9(2) . . ?
C00F C008 C009 134.6(3) . . ?
C00F C008 C00E 118.3(3) . . ?
C008 C009 C006 129.2(3) . . ?
C00A C009 C006 124.5(2) . . ?
C00A C009 C008 106.2(2) . . ?
N007 C00A C009 109.9(2) . . ?
N007 C00A C00I 118.5(3) . . ?
C009 C00A C00I 131.6(3) . . ?
C00J C00B C00D 118.9(3) . . ?
C00K C00B C00D 123.5(3) . . ?
C00K C00B C00J 117.6(3) . . ?
N003 C00C H00C 118.7 . . ?
C00D C00C N003 122.6(2) . . ?
C00D C00C H00C 118.7 . . ?
C00B C00D H00D 116.8 . . ?
C00C C00D C00B 126.3(3) . . ?
C00C C00D H00D 116.8 . . ?
N007 C00E C008 107.8(2) . . ?
N007 C00E C00H 129.1(3) . . ?
C00H C00E C008 123.2(3) . . ?
C008 C00F H00F 120.8 . . ?
C00G C00F C008 118.4(3) . . ?
C00G C00F H00F 120.8 . . ?
C00F C00G H00G 119.0 . . ?
C00F C00G C00L 122.0(3) . . ?
C00L C00G H00G 119.0 . . ?
C00E C00H H00H 121.6 . . ?
C00L C00H C00E 116.8(3) . . ?
C00L C00H H00H 121.6 . . ?
F002 C00I F004 106.1(3) . . ?
F002 C00I F005 106.7(3) . . ?
F002 C00I C00A 113.6(3) . . ?
F004 C00I F005 106.9(3) . . ?
F004 C00I C00A 112.9(3) . . ?
F005 C00I C00A 110.2(3) . . ?
C00B C00J H00J 119.5 . . ?
C00M C00J C00B 121.1(3) . . ?
C00M C00J H00J 119.5 . . ?
C00B C00K H00K 119.5 . . ?
C00N C00K C00B 120.9(4) . . ?
C00N C00K H00K 119.5 . . ?
C00G C00L H00L 119.4 . . ?
C00H C00L C00G 121.2(3) . . ?
C00H C00L H00L 119.4 . . ?
C00J C00M H00M 119.9 . . ?
C00O C00M C00J 120.2(4) . . ?
C00O C00M H00M 119.9 . . ?
C00K C00N H00N 119.8 . . ?
C00O C00N C00K 120.4(4) . . ?
C00O C00N H00N 119.8 . . ?
C00M C00O H00O 120.1 . . ?
C00N C00O C00M 119.8(4) . . ?
C00N C00O H00O 120.1 . . ?

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
O001 C006 C009 C008 152.1(3) . . . . ?
O001 C006 C009 C00A -28.6(4) . . . . ?
N003 C006 C009 C008 -28.5(4) . . . . ?
N003 C006 C009 C00A 150.8(3) . . . . ?
N003 C00C C00D C00B -178.5(3) . . . . ?
C006 N003 C00C C00D 173.7(3) . . . . ?
C006 C009 C00A N007 -177.5(3) . . . . ?
C006 C009 C00A C00I 3.3(6) . . . . ?
N007 C00A C00I F002 132.3(3) . . . . ?
N007 C00A C00I F004 -106.8(4) . . . . ?
N007 C00A C00I F005 12.6(5) . . . . ?
N007 C00E C00H C00L 177.5(4) . . . . ?
C008 C009 C00A N007 1.9(4) . . . . ?
C008 C009 C00A C00I -177.3(4) . . . . ?
C008 C00E C00H C00L -2.1(5) . . . . ?
C008 C00F C00G C00L -0.2(5) . . . . ?
C009 C008 C00E N007 1.0(3) . . . . ?
C009 C008 C00E C00H -179.4(3) . . . . ?
C009 C008 C00F C00G -178.4(3) . . . . ?
C009 C00A C00I F002 -48.5(5) . . . . ?
C009 C00A C00I F004 72.4(5) . . . . ?
C009 C00A C00I F005 -168.2(4) . . . . ?
C00A N007 C00E C008 0.2(4) . . . . ?
C00A N007 C00E C00H -179.4(3) . . . . ?
C00B C00J C00M C00O -1.4(6) . . . . ?
C00B C00K C00N C00O 0.6(7) . . . . ?
C00C N003 C006 O001 -2.6(4) . . . . ?
C00C N003 C006 C009 177.9(3) . . . . ?
C00D C00B C00J C00M -177.2(3) . . . . ?
C00D C00B C00K C00N 177.6(4) . . . . ?
C00E N007 C00A C009 -1.4(4) . . . . ?
C00E N007 C00A C00I 178.0(3) . . . . ?
C00E C008 C009 C006 177.6(3) . . . . ?
C00E C008 C009 C00A -1.8(3) . . . . ?
C00E C008 C00F C00G -2.2(4) . . . . ?
C00E C00H C00L C00G -0.4(5) . . . . ?
C00F C008 C009 C006 -5.9(5) . . . . ?
C00F C008 C009 C00A 174.7(3) . . . . ?
C00F C008 C00E N007 -176.2(3) . . . . ?
C00F C008 C00E C00H 3.4(5) . . . . ?
C00F C00G C00L C00H 1.6(6) . . . . ?
C00J C00B C00D C00C 176.0(3) . . . . ?
C00J C00B C00K C00N -1.5(6) . . . . ?
C00J C00M C00O C00N 0.5(7) . . . . ?
C00K C00B C00D C00C -3.1(5) . . . . ?
C00K C00B C00J C00M 1.9(5) . . . . ?
C00K C00N C00O C00M -0.1(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cjh_633_0ma
_database_code_depnum_ccdc_archive 'CCDC 2334396'
_audit_update_record             
;
2024-02-21 deposited with the CCDC.	2024-12-01 downloaded from the CCDC.
;
_audit_creation_date             2023-11-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 Br F3 N2 O2 S'
_chemical_formula_sum            'C18 H16 Br F3 N2 O2 S'
_chemical_formula_weight         461.30
_chemical_melting_point          ?
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'
Br Br -0.6763 1.2805 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   16.5134(7)
_cell_length_b                   8.0265(4)
_cell_length_c                   16.5356(7)
_cell_angle_alpha                90
_cell_angle_beta                 117.207(2)
_cell_angle_gamma                90
_cell_volume                     1949.22(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1915
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      67.297
_cell_measurement_theta_min      9.628
_shelx_estimated_absorpt_T_max   0.482
_shelx_estimated_absorpt_T_min   0.414
_exptl_absorpt_coefficient_mu    4.278
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1429 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.5629.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30846
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.272
_diffrn_reflns_theta_min         6.026
_diffrn_ambient_temperature      295.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3284
_reflns_number_total             3476
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0609P)²+1.8786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1292
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Br1A-C16 \\sim Br1B-C16
 with sigma of 0.02
3. Others
 Sof(Br1B)=1-FVAR(1)
 Sof(Br1A)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C14(H14), C17(H17), C5(H5), C15(H15), C18(H18), C1(H1), C4(H4),
 C2(H2A), C3(H3)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1A Br 0.8481(4) 0.5723(7) 0.6045(4) 0.0585(9) Uani 0.47(4) 1 d D . P A 1
S1 S 0.35539(5) 0.44897(8) 0.75092(5) 0.0374(2) Uani 1 1 d . . . . .
O2 O 0.49566(17) 0.4014(2) 0.69190(19) 0.0556(6) Uani 1 1 d . . . . .
O1 O 0.28771(15) 0.5263(3) 0.77142(17) 0.0536(6) Uani 1 1 d . . . . .
F3 F 0.4355(2) 0.6375(3) 0.93042(15) 0.0894(9) Uani 1 1 d . . . . .
N1 N 0.42326(18) 0.8960(3) 0.75932(18) 0.0427(6) Uani 1 1 d . . . . .
N2 N 0.56141(18) 0.6563(3) 0.7321(2) 0.0462(6) Uani 1 1 d . . . . .
H2 H 0.562979 0.747075 0.760471 0.055 Uiso 1 1 calc R U . . .
F1 F 0.4295(3) 0.8955(4) 0.92060(18) 0.1139(12) Uani 1 1 d . . . . .
F2 F 0.54956(18) 0.7719(6) 0.94402(17) 0.1256(14) Uani 1 1 d . . . . .
C12 C 0.4964(2) 0.5406(3) 0.7238(2) 0.0399(6) Uani 1 1 d . . . . .
C13 C 0.6256(2) 0.6399(3) 0.6985(2) 0.0392(6) Uani 1 1 d . . . . .
C7 C 0.43227(19) 0.7537(3) 0.79611(19) 0.0366(6) Uani 1 1 d . . . . .
C6 C 0.3937(2) 0.9140(3) 0.6646(2) 0.0445(7) Uani 1 1 d . . . . .
C14 C 0.6075(2) 0.5515(4) 0.6197(2) 0.0472(7) Uani 1 1 d . . . . .
H14 H 0.551466 0.499258 0.587374 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4337(2) 0.5905(3) 0.7567(2) 0.0375(6) Uani 1 1 d . . . . .
C8 C 0.4609(2) 0.7635(4) 0.8974(2) 0.0477(7) Uani 1 1 d . . . . .
C17 C 0.7743(2) 0.7085(4) 0.7152(2) 0.0499(7) Uani 1 1 d . . . . .
H17 H 0.830037 0.761985 0.746574 0.060 Uiso 1 1 calc R U . . .
C16 C 0.7554(2) 0.6183(4) 0.6379(2) 0.0466(7) Uani 1 1 d D . . . .
C5 C 0.4465(3) 1.0109(4) 0.6373(3) 0.0575(9) Uani 1 1 d . . . . .
H5 H 0.501419 1.055160 0.680421 0.069 Uiso 1 1 calc R U . . .
C15 C 0.6723(2) 0.5412(5) 0.5894(2) 0.0503(8) Uani 1 1 d . . . . .
H15 H 0.660116 0.482516 0.536590 0.060 Uiso 1 1 calc R U . . .
C18 C 0.7094(2) 0.7184(4) 0.7454(2) 0.0485(7) Uani 1 1 d . . . . .
H18 H 0.721835 0.778463 0.797880 0.058 Uiso 1 1 calc R U . . .
C10 C 0.4059(3) 0.2777(4) 0.8228(3) 0.0553(8) Uani 1 1 d . . . . .
H10A H 0.430776 0.312799 0.885074 0.083 Uiso 1 1 calc R U . . .
H10B H 0.453702 0.233552 0.811316 0.083 Uiso 1 1 calc R U . . .
H10C H 0.360809 0.193109 0.811280 0.083 Uiso 1 1 calc R U . . .
C1 C 0.3110(3) 0.8531(5) 0.6010(2) 0.0589(9) Uani 1 1 d . . . . .
H1 H 0.275132 0.789558 0.619246 0.071 Uiso 1 1 calc R U . . .
C11 C 0.3022(2) 0.3562(5) 0.6426(2) 0.0588(9) Uani 1 1 d . . . . .
H11A H 0.259324 0.274225 0.641271 0.088 Uiso 1 1 calc R U . . .
H11B H 0.347390 0.303763 0.629862 0.088 Uiso 1 1 calc R U . . .
H11C H 0.271013 0.440098 0.597644 0.088 Uiso 1 1 calc R U . . .
C4 C 0.4174(4) 1.0413(5) 0.5461(3) 0.0776(13) Uani 1 1 d . . . . .
H4 H 0.453474 1.103634 0.527663 0.093 Uiso 1 1 calc R U . . .
C2 C 0.2815(4) 0.8870(6) 0.5096(3) 0.0823(13) Uani 1 1 d . . . . .
H2A H 0.225450 0.847160 0.466407 0.099 Uiso 1 1 calc R U . . .
C3 C 0.3354(4) 0.9802(6) 0.4826(3) 0.0861(14) Uani 1 1 d . . . . .
H3 H 0.316005 1.001285 0.421165 0.103 Uiso 1 1 calc R U . . .
Br1B Br 0.8460(3) 0.613(2) 0.5961(5) 0.0801(16) Uani 0.53(4) 1 d 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
Br1A C16 1.886(6) . ?
S1 O1 1.448(2) . ?
S1 C9 1.691(3) . ?
S1 C10 1.759(3) . ?
S1 C11 1.759(3) . ?
O2 C12 1.234(3) . ?
F3 C8 1.306(4) . ?
N1 C7 1.270(4) . ?
N1 C6 1.420(4) . ?
N2 H2 0.8600 . ?
N2 C12 1.378(4) . ?
N2 C13 1.411(4) . ?
F1 C8 1.312(4) . ?
F2 C8 1.308(4) . ?
C12 C9 1.430(4) . ?
C13 C14 1.391(4) . ?
C13 C18 1.391(4) . ?
C7 C9 1.468(4) . ?
C7 C8 1.520(4) . ?
C6 C5 1.388(5) . ?
C6 C1 1.378(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.375(5) . ?
C17 C18 1.375(4) . ?
C16 C15 1.380(5) . ?
C16 Br1B 1.915(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.379(6) . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C1 H1 0.9300 . ?
C1 C2 1.386(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C3 1.369(7) . ?
C2 H2A 0.9300 . ?
C2 C3 1.384(7) . ?
C3 H3 0.9300 . ?

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
O1 S1 C9 110.56(14) . . ?
O1 S1 C10 110.82(16) . . ?
O1 S1 C11 109.91(17) . . ?
C9 S1 C10 111.88(16) . . ?
C9 S1 C11 110.77(17) . . ?
C10 S1 C11 102.65(19) . . ?
C7 N1 C6 121.8(2) . . ?
C12 N2 H2 117.0 . . ?
C12 N2 C13 126.1(2) . . ?
C13 N2 H2 117.0 . . ?
O2 C12 N2 120.6(3) . . ?
O2 C12 C9 123.3(3) . . ?
N2 C12 C9 116.1(2) . . ?
C14 C13 N2 122.6(3) . . ?
C18 C13 N2 118.3(3) . . ?
C18 C13 C14 119.1(3) . . ?
N1 C7 C9 127.7(3) . . ?
N1 C7 C8 113.0(2) . . ?
C9 C7 C8 118.4(2) . . ?
C5 C6 N1 117.8(3) . . ?
C1 C6 N1 121.8(3) . . ?
C1 C6 C5 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C12 C9 S1 117.3(2) . . ?
C12 C9 C7 125.5(2) . . ?
C7 C9 S1 117.2(2) . . ?
F3 C8 F1 104.9(3) . . ?
F3 C8 F2 106.3(3) . . ?
F3 C8 C7 115.0(3) . . ?
F1 C8 C7 113.5(3) . . ?
F2 C8 F1 105.7(3) . . ?
F2 C8 C7 110.7(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C18 C17 C16 119.0(3) . . ?
C17 C16 Br1A 120.4(3) . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 Br1B 117.7(4) . . ?
C15 C16 Br1A 117.9(3) . . ?
C15 C16 Br1B 121.0(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 H5 120.1 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.9(3) . . ?
C17 C18 H18 119.6 . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C1 H1 120.2 . . ?
C6 C1 C2 119.6(4) . . ?
C2 C1 H1 120.2 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.9 . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 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
Br1A C16 C15 C14 170.4(3) . . . . ?
O2 C12 C9 S1 0.1(4) . . . . ?
O2 C12 C9 C7 179.3(3) . . . . ?
O1 S1 C9 C12 -169.9(2) . . . . ?
O1 S1 C9 C7 10.7(3) . . . . ?
N1 C7 C9 S1 -122.5(3) . . . . ?
N1 C7 C9 C12 58.2(5) . . . . ?
N1 C7 C8 F3 152.7(3) . . . . ?
N1 C7 C8 F1 31.8(4) . . . . ?
N1 C7 C8 F2 -86.8(4) . . . . ?
N1 C6 C5 C4 -175.6(3) . . . . ?
N1 C6 C1 C2 174.1(3) . . . . ?
N2 C12 C9 S1 -177.9(2) . . . . ?
N2 C12 C9 C7 1.4(4) . . . . ?
N2 C13 C14 C15 179.2(3) . . . . ?
N2 C13 C18 C17 -179.2(3) . . . . ?
C12 N2 C13 C14 31.8(5) . . . . ?
C12 N2 C13 C18 -149.6(3) . . . . ?
C13 N2 C12 O2 7.0(5) . . . . ?
C13 N2 C12 C9 -174.9(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C7 N1 C6 C5 -127.7(3) . . . . ?
C7 N1 C6 C1 59.0(4) . . . . ?
C6 N1 C7 C9 13.7(5) . . . . ?
C6 N1 C7 C8 -177.7(3) . . . . ?
C6 C5 C4 C3 1.8(6) . . . . ?
C6 C1 C2 C3 0.6(7) . . . . ?
C14 C13 C18 C17 -0.5(5) . . . . ?
C9 C7 C8 F3 -37.5(4) . . . . ?
C9 C7 C8 F1 -158.4(3) . . . . ?
C9 C7 C8 F2 83.0(4) . . . . ?
C8 C7 C9 S1 69.4(3) . . . . ?
C8 C7 C9 C12 -109.9(3) . . . . ?
C17 C16 C15 C14 -1.3(5) . . . . ?
C16 C17 C18 C13 -0.5(5) . . . . ?
C5 C6 C1 C2 1.0(5) . . . . ?
C5 C4 C3 C2 -0.2(7) . . . . ?
C18 C13 C14 C15 0.6(5) . . . . ?
C18 C17 C16 Br1A -170.1(3) . . . . ?
C18 C17 C16 C15 1.4(5) . . . . ?
C18 C17 C16 Br1B 178.2(7) . . . . ?
C10 S1 C9 C12 66.0(3) . . . . ?
C10 S1 C9 C7 -113.3(3) . . . . ?
C1 C6 C5 C4 -2.2(5) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C11 S1 C9 C12 -47.8(3) . . . . ?
C11 S1 C9 C7 132.8(2) . . . . ?
Br1B C16 C15 C14 -178.0(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
