# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_kb615_0m
_database_code_depnum_ccdc_archive 'CCDC 2217740'
loop_
_audit_author_name
_audit_author_address
'Suresh R N'
;University of Mysore
India
;
_audit_update_record             
;
2022-11-06 deposited with the CCDC.	2023-01-25 downloaded from the CCDC.
;
_audit_creation_date             2022-11-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N O2 S'
_chemical_formula_sum            'C17 H13 N O2 S'
_chemical_formula_weight         295.34
_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'
S S 0.1246 0.1234 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4137(6)
_cell_length_b                   5.5560(3)
_cell_length_c                   21.0115(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.6231(19)
_cell_angle_gamma                90
_cell_volume                     1447.66(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8791
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.8565
_cell_measurement_theta_min      3.2855
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23098
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.482
_diffrn_reflns_theta_min         1.642
_diffrn_ambient_temperature      294.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2775
_reflns_number_total             4251
_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 (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.021
_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)+(0.0432P)²+0.4472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.49538(14) 0.7550(3) 0.36238(8) 0.0568(4) Uani 1 1 d . . . . .
C2 C 0.46056(15) 0.7105(3) 0.42334(8) 0.0607(5) Uani 1 1 d . . . . .
H2 H 0.485930 0.804223 0.457502 0.073 Uiso 1 1 calc R U . . .
C3 C 0.38872(15) 0.5280(3) 0.43278(7) 0.0597(5) Uani 1 1 d . . . . .
H3 H 0.366365 0.499813 0.473761 0.072 Uiso 1 1 calc R U . . .
C4 C 0.34783(13) 0.3825(3) 0.38296(7) 0.0517(4) Uani 1 1 d . . . . .
C5 C 0.38303(14) 0.4315(3) 0.32186(7) 0.0594(4) Uani 1 1 d . . . . .
H5 H 0.357259 0.339309 0.287504 0.071 Uiso 1 1 calc R U . . .
C6 C 0.45479(16) 0.6133(4) 0.31208(8) 0.0660(5) Uani 1 1 d . . . . .
H6 H 0.476891 0.642790 0.271104 0.079 Uiso 1 1 calc R U . . .
C7 C 0.27241(14) 0.1888(3) 0.39809(7) 0.0575(4) Uani 1 1 d . . . . .
C8 C 0.21537(12) 0.0413(3) 0.34757(7) 0.0513(4) Uani 1 1 d . . . . .
C9 C 0.10965(14) -0.2656(3) 0.29419(8) 0.0594(4) Uani 1 1 d . . . . .
H9 H 0.067394 -0.395248 0.280353 0.071 Uiso 1 1 calc R U . . .
C10 C 0.15308(12) -0.1002(3) 0.25453(7) 0.0474(3) Uani 1 1 d . . . . .
C11 C 0.14134(12) -0.0936(3) 0.18424(7) 0.0473(3) Uani 1 1 d . . . . .
C12 C 0.08406(18) -0.2668(4) 0.15040(9) 0.0754(6) Uani 1 1 d . . . . .
H12 H 0.051978 -0.391822 0.172050 0.090 Uiso 1 1 calc R U . . .
C13 C 0.0735(2) -0.2576(5) 0.08468(10) 0.0877(7) Uani 1 1 d . . . . .
H13 H 0.034780 -0.376885 0.062595 0.105 Uiso 1 1 calc R U . . .
C14 C 0.11906(16) -0.0762(4) 0.05209(9) 0.0732(5) Uani 1 1 d . . . . .
H14 H 0.112295 -0.071304 0.007841 0.088 Uiso 1 1 calc R U . . .
C15 C 0.17482(18) 0.0987(4) 0.08488(9) 0.0778(6) Uani 1 1 d . . . . .
H15 H 0.205348 0.224948 0.062918 0.093 Uiso 1 1 calc R U . . .
C16 C 0.18639(16) 0.0897(4) 0.15069(8) 0.0656(5) Uani 1 1 d . . . . .
H16 H 0.225224 0.209593 0.172458 0.079 Uiso 1 1 calc R U . . .
C17 C 0.61050(17) 1.0815(4) 0.39634(10) 0.0775(6) Uani 1 1 d . . . . .
H17A H 0.662140 1.188574 0.378843 0.116 Uiso 1 1 calc R U . . .
H17B H 0.645278 0.985889 0.429330 0.116 Uiso 1 1 calc R U . . .
H17C H 0.553493 1.173582 0.413844 0.116 Uiso 1 1 calc R U . . .
N1 N 0.21290(10) 0.0744(2) 0.28588(6) 0.0497(3) Uani 1 1 d . . . . .
O1 O 0.25354(13) 0.1371(3) 0.45332(5) 0.0836(4) Uani 1 1 d . . . . .
O2 O 0.56678(11) 0.9276(3) 0.34730(6) 0.0730(4) Uani 1 1 d . . . . .
S1 S 0.14243(4) -0.20475(10) 0.37160(2) 0.06490(17) Uani 1 1 d . . . . .


_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
C1 C2 1.393(2) . ?
C1 C6 1.394(2) . ?
C1 O2 1.353(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(2) . ?
C4 C5 1.402(2) . ?
C4 C7 1.471(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.368(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.494(2) . ?
C7 O1 1.2284(19) . ?
C8 N1 1.3082(18) . ?
C8 S1 1.7277(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(2) . ?
C9 S1 1.6926(19) . ?
C10 C11 1.478(2) . ?
C10 N1 1.372(2) . ?
C11 C12 1.375(2) . ?
C11 C16 1.372(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.357(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.362(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 O2 1.427(2) . ?

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
C2 C1 C6 118.72(18) . . ?
O2 C1 C2 125.13(16) . . ?
O2 C1 C6 116.15(16) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.72(16) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.36(15) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 117.08(17) . . ?
C3 C4 C7 118.28(14) . . ?
C5 C4 C7 124.64(15) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.89(16) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.22(16) . . ?
C5 C6 H6 119.4 . . ?
C4 C7 C8 122.26(13) . . ?
O1 C7 C4 121.74(16) . . ?
O1 C7 C8 115.99(18) . . ?
C7 C8 S1 117.67(11) . . ?
N1 C8 C7 128.01(16) . . ?
N1 C8 S1 114.33(13) . . ?
C10 C9 H9 124.2 . . ?
C10 C9 S1 111.55(14) . . ?
S1 C9 H9 124.2 . . ?
C9 C10 C11 127.02(15) . . ?
C9 C10 N1 113.72(14) . . ?
N1 C10 C11 119.26(13) . . ?
C12 C11 C10 121.62(15) . . ?
C16 C11 C10 120.54(14) . . ?
C16 C11 C12 117.84(15) . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.94(18) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.59(19) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.26(17) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.46(18) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.90(17) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
C8 N1 C10 111.35(14) . . ?
C1 O2 C17 119.15(16) . . ?
C9 S1 C8 89.04(8) . . ?

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
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
C2 C1 O2 C17 -0.9(3) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C4 C7 179.07(15) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C3 C4 C7 C8 173.31(14) . . . . ?
C3 C4 C7 O1 -7.5(2) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C7 C8 N1 -8.2(3) . . . . ?
C4 C7 C8 S1 171.94(12) . . . . ?
C5 C4 C7 C8 -7.3(2) . . . . ?
C5 C4 C7 O1 171.84(17) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C6 C1 O2 C17 179.16(16) . . . . ?
C7 C4 C5 C6 -178.98(16) . . . . ?
C7 C8 N1 C10 179.22(15) . . . . ?
C7 C8 S1 C9 -179.21(13) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C9 C10 C11 C16 177.47(17) . . . . ?
C9 C10 N1 C8 0.43(19) . . . . ?
C10 C9 S1 C8 -0.66(13) . . . . ?
C10 C11 C12 C13 179.8(2) . . . . ?
C10 C11 C16 C15 -179.32(18) . . . . ?
C11 C10 N1 C8 -179.73(13) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C12 C11 C16 C15 -0.3(3) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
N1 C8 S1 C9 0.95(13) . . . . ?
N1 C10 C11 C12 178.70(16) . . . . ?
N1 C10 C11 C16 -2.3(2) . . . . ?
O1 C7 C8 N1 172.55(16) . . . . ?
O1 C7 C8 S1 -7.3(2) . . . . ?
O2 C1 C2 C3 -179.19(16) . . . . ?
O2 C1 C6 C5 179.24(16) . . . . ?
S1 C8 N1 C10 -0.96(17) . . . . ?
S1 C9 C10 C11 -179.53(13) . . . . ?
S1 C9 C10 N1 0.28(18) . . . . ?

_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_kb548_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2221383'
loop_
_audit_author_name
_audit_author_address
'Suresh R N'
;University of Mysore
India
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-01-25 downloaded from the CCDC.
;
_audit_creation_date             2022-11-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 F2 O2 S'
_chemical_formula_sum            'C16 H12 F2 O2 S'
_chemical_formula_weight         306.32
_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 0.0033 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'
F F 0.0171 0.0103 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   31.4723(3)
_cell_length_b                   8.4394(5)
_cell_length_c                   5.347(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1420.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6060
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.4985
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            17152
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.790
_diffrn_reflns_theta_min         2.499
_diffrn_ambient_temperature      294.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2769
_reflns_number_total             4415
_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 (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 980 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4415
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.028
_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)+(0.0612P)²+0.1307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1340
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.57066(12) 0.4137(5) 0.4471(7) 0.0732(10) Uani 1 1 d . . . . .
H1 H 0.564123 0.476591 0.584663 0.088 Uiso 1 1 calc R U . . .
C2 C 0.53936(11) 0.3550(5) 0.2982(8) 0.0731(10) Uani 1 1 d . . . . .
C3 C 0.54761(12) 0.2662(6) 0.0934(8) 0.0844(12) Uani 1 1 d . . . . .
H3 H 0.525503 0.227534 -0.004607 0.101 Uiso 1 1 calc R U . . .
C4 C 0.58933(11) 0.2336(4) 0.0317(7) 0.0711(9) Uani 1 1 d . . . . .
H4 H 0.595344 0.175076 -0.111380 0.085 Uiso 1 1 calc R U . . .
C5 C 0.62213(9) 0.2871(4) 0.1803(6) 0.0528(7) Uani 1 1 d . . . . .
C6 C 0.61235(11) 0.3779(4) 0.3897(6) 0.0662(8) Uani 1 1 d . . . . .
H6 H 0.634100 0.414866 0.492026 0.079 Uiso 1 1 calc R U . . .
C7 C 0.66605(10) 0.2412(4) 0.1143(6) 0.0571(7) Uani 1 1 d . . . . .
C8 C 0.70110(10) 0.2831(4) 0.2970(7) 0.0655(9) Uani 1 1 d . . . . .
H8A H 0.692519 0.254060 0.465056 0.079 Uiso 1 1 calc R U . . .
H8B H 0.706084 0.396487 0.293595 0.079 Uiso 1 1 calc R U . . .
C9 C 0.78054(10) 0.2570(4) 0.4681(7) 0.0652(8) Uani 1 1 d . . . . .
H9A H 0.781066 0.371809 0.458672 0.078 Uiso 1 1 calc R U . . .
H9B H 0.767613 0.227534 0.626074 0.078 Uiso 1 1 calc R U . . .
C10 C 0.82535(11) 0.1946(4) 0.4589(6) 0.0589(7) Uani 1 1 d . . . . .
C11 C 0.85728(10) 0.2658(4) 0.6268(5) 0.0547(7) Uani 1 1 d . . . . .
C12 C 0.90024(11) 0.2441(4) 0.5764(7) 0.0724(10) Uani 1 1 d . . . . .
H12 H 0.908354 0.182084 0.440794 0.087 Uiso 1 1 calc R U . . .
C13 C 0.93085(11) 0.3128(5) 0.7237(9) 0.0808(10) Uani 1 1 d . . . . .
H13 H 0.959544 0.299982 0.687475 0.097 Uiso 1 1 calc R U . . .
C14 C 0.91801(11) 0.4009(5) 0.9261(7) 0.0729(10) Uani 1 1 d . . . . .
C15 C 0.87663(11) 0.4248(4) 0.9846(7) 0.0661(8) Uani 1 1 d . . . . .
H15 H 0.869026 0.484867 1.123312 0.079 Uiso 1 1 calc R U . . .
C16 C 0.84598(10) 0.3575(4) 0.8327(6) 0.0612(8) Uani 1 1 d . . . . .
H16 H 0.817396 0.373823 0.868664 0.073 Uiso 1 1 calc R U . . .
O1 O 0.67421(8) 0.1675(3) -0.0747(5) 0.0749(7) Uani 1 1 d . . . . .
O2 O 0.83455(8) 0.0904(3) 0.3129(6) 0.0842(8) Uani 1 1 d . . . . .
S1 S 0.74923(3) 0.18024(11) 0.2160(2) 0.0643(3) Uani 1 1 d . . . . .
F1 F 0.49848(6) 0.3889(4) 0.3568(6) 0.1056(8) Uani 1 1 d . . . . .
F2 F 0.94866(7) 0.4679(3) 1.0716(5) 0.0995(8) Uani 1 1 d . . . . .


_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
C1 H1 0.9300 . ?
C1 C2 1.360(5) . ?
C1 C6 1.381(5) . ?
C2 C3 1.353(6) . ?
C2 F1 1.355(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(4) . ?
C5 C6 1.392(4) . ?
C5 C7 1.478(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.515(4) . ?
C7 O1 1.214(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 S1 1.798(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.506(4) . ?
C9 S1 1.791(4) . ?
C10 C11 1.476(5) . ?
C10 O2 1.211(4) . ?
C11 C12 1.391(4) . ?
C11 C16 1.392(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(6) . ?
C14 C15 1.354(5) . ?
C14 F2 1.362(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(5) . ?
C16 H16 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
C2 C1 H1 120.7 . . ?
C2 C1 C6 118.6(3) . . ?
C6 C1 H1 120.7 . . ?
C3 C2 C1 122.5(3) . . ?
C3 C2 F1 119.1(4) . . ?
F1 C2 C1 118.4(4) . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.1(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 C7 118.5(3) . . ?
C6 C5 C7 122.9(3) . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C5 C7 C8 117.8(3) . . ?
O1 C7 C5 122.0(3) . . ?
O1 C7 C8 120.1(3) . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C7 C8 S1 110.2(2) . . ?
H8A C8 H8B 108.1 . . ?
S1 C8 H8A 109.6 . . ?
S1 C8 H8B 109.6 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C10 C9 S1 111.3(2) . . ?
S1 C9 H9A 109.4 . . ?
S1 C9 H9B 109.4 . . ?
C11 C10 C9 118.4(3) . . ?
O2 C10 C9 119.9(3) . . ?
O2 C10 C11 121.7(3) . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 C16 118.4(3) . . ?
C16 C11 C10 122.3(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.3(3) . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 123.0(3) . . ?
C15 C14 F2 119.2(4) . . ?
F2 C14 C13 117.8(3) . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C16 118.3(3) . . ?
C16 C15 H15 120.8 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 119.5 . . ?
C9 S1 C8 96.18(15) . . ?

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
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C1 C6 C5 1.6(6) . . . . ?
C2 C3 C4 C5 1.8(7) . . . . ?
C3 C4 C5 C6 -1.7(6) . . . . ?
C3 C4 C5 C7 176.5(3) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
C4 C5 C7 C8 -172.4(3) . . . . ?
C4 C5 C7 O1 5.1(5) . . . . ?
C5 C7 C8 S1 167.4(2) . . . . ?
C6 C1 C2 C3 -1.5(6) . . . . ?
C6 C1 C2 F1 179.2(3) . . . . ?
C6 C5 C7 C8 5.7(5) . . . . ?
C6 C5 C7 O1 -176.9(3) . . . . ?
C7 C5 C6 C1 -178.1(3) . . . . ?
C7 C8 S1 C9 -179.3(3) . . . . ?
C9 C10 C11 C12 -162.1(3) . . . . ?
C9 C10 C11 C16 16.5(5) . . . . ?
C10 C9 S1 C8 -179.4(3) . . . . ?
C10 C11 C12 C13 177.9(3) . . . . ?
C10 C11 C16 C15 -179.0(3) . . . . ?
C11 C12 C13 C14 1.4(6) . . . . ?
C12 C11 C16 C15 -0.4(5) . . . . ?
C12 C13 C14 C15 -0.9(6) . . . . ?
C12 C13 C14 F2 179.7(4) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C11 0.8(5) . . . . ?
C16 C11 C12 C13 -0.8(5) . . . . ?
O1 C7 C8 S1 -10.1(4) . . . . ?
O2 C10 C11 C12 16.6(5) . . . . ?
O2 C10 C11 C16 -164.8(3) . . . . ?
S1 C9 C10 C11 170.0(2) . . . . ?
S1 C9 C10 O2 -8.7(5) . . . . ?
F1 C2 C3 C4 179.1(4) . . . . ?
F2 C14 C15 C16 179.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
