# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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. 
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data_6145f
_database_code_depnum_ccdc_archive 'CCDC 2143596'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2022-01-21 deposited with the CCDC.	2022-05-05 downloaded from the CCDC.
;
_audit_creation_date             2019-10-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        SAV-18
_chemical_formula_moiety         'C17 H14 Br F2 N3 O3 S'
_chemical_formula_sum            'C17 H14 Br F2 N3 O3 S'
_chemical_formula_weight         458.28
_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 0.0033 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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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'
Br Br -0.2901 2.4595 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4327(4)
_cell_length_b                   7.6898(6)
_cell_length_c                   18.8782(14)
_cell_angle_alpha                90.654(4)
_cell_angle_beta                 91.728(4)
_cell_angle_gamma                103.495(4)
_cell_volume                     907.47(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6464
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.10
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.618
_exptl_absorpt_coefficient_mu    2.423
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6154
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1135 before and 0.0661 after correction. The Ratio of minimum to maximum transmission is 0.8249. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33623
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.724
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3301
_reflns_number_total             4393
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.736
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.009
_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)+(0.0342P)²+0.6512P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0841
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3A), C5(H5), C7(H7), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Br Br 0.32292(4) 0.97021(4) 0.11297(2) 0.02263(9) Uani 1 1 d . . . . .
S S -0.28324(11) 0.76786(9) -0.45913(4) 0.01920(16) Uani 1 1 d . . . . .
F1 F -0.2028(3) 0.7437(2) -0.27621(8) 0.0241(4) Uani 1 1 d . . . . .
F2 F 0.3165(3) 0.4094(2) -0.24832(9) 0.0304(4) Uani 1 1 d . . . . .
O1 O 0.3111(3) 0.7492(3) -0.17655(11) 0.0292(5) Uani 1 1 d . . . . .
O2 O -0.0648(3) 0.8066(3) -0.47932(11) 0.0273(5) Uani 1 1 d . . . . .
O3 O -0.4501(3) 0.7290(3) -0.51368(10) 0.0256(5) Uani 1 1 d . . . . .
N1 N -0.3424(3) 0.5332(3) -0.08002(12) 0.0197(5) Uani 1 1 d . . . . .
H1 H -0.4761 0.4780 -0.0732 0.024 Uiso 1 1 calc R . . . .
N2 N -0.2502(3) 0.6592(3) 0.03680(12) 0.0199(5) Uani 1 1 d . . . . .
N3 N -0.3311(4) 0.5918(3) -0.40865(12) 0.0183(5) Uani 1 1 d . . . . .
H3 H -0.4367 0.5932 -0.3819 0.022 Uiso 1 1 d R . . . .
C1 C -0.0321(4) 0.6350(4) -0.13366(14) 0.0175(6) Uani 1 1 d . . . . .
C2 C -0.0047(4) 0.6990(4) -0.06133(14) 0.0168(6) Uani 1 1 d . . . . .
C3 C 0.1597(4) 0.8022(4) -0.01856(14) 0.0184(6) Uani 1 1 d . . . . .
H3A H 0.2977 0.8502 -0.0362 0.022 Uiso 1 1 calc R . . . .
C4 C 0.1115(4) 0.8310(4) 0.05057(14) 0.0185(6) Uani 1 1 d . . . . .
C5 C -0.0908(4) 0.7597(4) 0.07658(15) 0.0213(6) Uani 1 1 d . . . . .
H5 H -0.1162 0.7836 0.1246 0.026 Uiso 1 1 calc R . . . .
C6 C -0.2034(4) 0.6322(4) -0.02988(14) 0.0165(6) Uani 1 1 d . . . . .
C7 C -0.2405(4) 0.5349(4) -0.14100(14) 0.0181(6) Uani 1 1 d . . . . .
H7 H -0.3030 0.4754 -0.1836 0.022 Uiso 1 1 calc R . . . .
C8 C 0.1271(4) 0.6649(4) -0.18691(14) 0.0198(6) Uani 1 1 d . . . . .
C9 C 0.0606(4) 0.5804(4) -0.25959(14) 0.0181(6) Uani 1 1 d . . . . .
C10 C -0.1006(4) 0.6226(4) -0.30155(14) 0.0171(6) Uani 1 1 d . . . . .
C11 C -0.1587(4) 0.5485(4) -0.36839(14) 0.0176(6) Uani 1 1 d . . . . .
C12 C -0.0506(4) 0.4283(4) -0.39469(15) 0.0207(6) Uani 1 1 d . . . . .
H12 H -0.0868 0.3778 -0.4409 0.025 Uiso 1 1 calc R . . . .
C13 C 0.1106(4) 0.3798(4) -0.35465(16) 0.0231(6) Uani 1 1 d . . . . .
H13 H 0.1838 0.2953 -0.3724 0.028 Uiso 1 1 calc R . . . .
C14 C 0.1614(4) 0.4578(4) -0.28844(15) 0.0207(6) Uani 1 1 d . . . . .
C15 C -0.3233(5) 0.9448(4) -0.40577(15) 0.0216(6) Uani 1 1 d . . . . .
H15A H -0.2125 0.9683 -0.3670 0.026 Uiso 1 1 calc R . . . .
H15B H -0.3026 1.0537 -0.4347 0.026 Uiso 1 1 calc R . . . .
C16 C -0.5411(5) 0.9127(4) -0.37344(17) 0.0298(7) Uani 1 1 d . . . . .
H16A H -0.5753 0.7933 -0.3516 0.036 Uiso 1 1 calc R . . . .
H16B H -0.6513 0.9148 -0.4110 0.036 Uiso 1 1 calc R . . . .
C17 C -0.5439(6) 1.0556(5) -0.31754(18) 0.0415(9) Uani 1 1 d . . . . .
H17A H -0.5076 1.1737 -0.3391 0.062 Uiso 1 1 calc GR . . . .
H17B H -0.4390 1.0499 -0.2794 0.062 Uiso 1 1 calc GR . . . .
H17C H -0.6868 1.0354 -0.2980 0.062 Uiso 1 1 calc GR . . . .


_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
Br C4 1.891(3) . ?
S O2 1.431(2) . ?
S O3 1.4414(19) . ?
S N3 1.640(2) . ?
S C15 1.755(3) . ?
F1 C10 1.350(3) . ?
F2 C14 1.357(3) . ?
O1 C8 1.218(3) . ?
N1 C6 1.375(3) . ?
N1 C7 1.341(4) . ?
N2 C5 1.335(3) . ?
N2 C6 1.329(3) . ?
N3 C11 1.430(3) . ?
C1 C2 1.438(4) . ?
C1 C7 1.383(4) . ?
C1 C8 1.439(4) . ?
C2 C3 1.394(3) . ?
C2 C6 1.413(4) . ?
C3 C4 1.378(4) . ?
C4 C5 1.396(4) . ?
C8 C9 1.517(4) . ?
C9 C10 1.386(4) . ?
C9 C14 1.379(4) . ?
C10 C11 1.383(4) . ?
C11 C12 1.377(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.377(4) . ?
C15 C16 1.514(4) . ?
C16 C17 1.518(5) . ?

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 S O3 118.95(13) . . ?
O2 S N3 109.59(12) . . ?
O2 S C15 108.86(13) . . ?
O3 S N3 104.66(12) . . ?
O3 S C15 108.46(13) . . ?
N3 S C15 105.50(13) . . ?
C7 N1 C6 108.7(2) . . ?
C6 N2 C5 115.2(2) . . ?
C11 N3 S 119.38(18) . . ?
C2 C1 C8 126.9(2) . . ?
C7 C1 C2 106.1(2) . . ?
C7 C1 C8 127.1(2) . . ?
C3 C2 C1 136.8(2) . . ?
C3 C2 C6 117.4(2) . . ?
C6 C2 C1 105.8(2) . . ?
C4 C3 C2 116.5(2) . . ?
C3 C4 Br 119.90(19) . . ?
C3 C4 C5 121.8(2) . . ?
C5 C4 Br 118.3(2) . . ?
N2 C5 C4 122.8(3) . . ?
N1 C6 C2 108.5(2) . . ?
N2 C6 N1 125.2(2) . . ?
N2 C6 C2 126.3(2) . . ?
N1 C7 C1 110.9(2) . . ?
O1 C8 C1 124.1(3) . . ?
O1 C8 C9 118.7(2) . . ?
C1 C8 C9 117.1(2) . . ?
C10 C9 C8 122.9(3) . . ?
C14 C9 C8 121.3(2) . . ?
C14 C9 C10 115.8(2) . . ?
F1 C10 C9 118.2(2) . . ?
F1 C10 C11 118.7(2) . . ?
C11 C10 C9 123.0(3) . . ?
C10 C11 N3 120.9(3) . . ?
C12 C11 N3 120.6(2) . . ?
C12 C11 C10 118.5(3) . . ?
C11 C12 C13 120.9(3) . . ?
C14 C13 C12 118.0(3) . . ?
F2 C14 C9 117.6(2) . . ?
F2 C14 C13 118.6(3) . . ?
C13 C14 C9 123.8(3) . . ?
C16 C15 S 114.7(2) . . ?
C15 C16 C17 110.3(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.88 1.98 2.841(3) 166.9 2_465
C3 H3A Br 0.95 2.94 3.876(3) 168.3 2_675
C7 H7 F2 0.95 2.64 3.388(3) 136.0 1_455
C12 H12 O2 0.95 2.43 3.178(4) 135.3 2_564
C15 H15A F1 0.99 2.46 3.083(3) 120.8 .

_olex2_submission_special_instructions 'No special instructions were received'

#END---------------------------------------------------------------------------


