# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_KA973_0m
_database_code_depnum_ccdc_archive 'CCDC 2004626'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2020-05-19 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 F3 N2 O2 S'
_chemical_formula_sum            'C15 H13 F3 N2 O2 S'
_chemical_formula_weight         342.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.0991(2)
_cell_length_b                   12.9247(2)
_cell_length_c                   10.4969(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.4740(7)
_cell_angle_gamma                90
_cell_volume                     1614.12(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8612
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      30.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5651
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18639
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.525
_diffrn_reflns_theta_max         30.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4444
_reflns_number_gt                3063
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²+0.8264P] 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         4444
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1791
_refine_ls_wR_factor_gt          0.1570
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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
C1 C 0.16511(17) 0.59666(18) 0.6599(2) 0.0490(5) Uani 1 1 d . . . . .
C2 C 0.10877(17) 0.49504(19) 0.6617(2) 0.0528(5) Uani 1 1 d . . . . .
C3 C 0.0403(2) 0.4580(3) 0.7436(3) 0.0773(8) Uani 1 1 d . . . . .
H3 H 0.023425 0.497873 0.811281 0.093 Uiso 1 1 calc R U . . .
C4 C -0.0017(3) 0.3590(3) 0.7201(4) 0.0959(13) Uani 1 1 d . . . . .
H4 H -0.048292 0.331807 0.773135 0.115 Uiso 1 1 calc R U . . .
C5 C 0.0232(3) 0.3005(3) 0.6214(5) 0.0950(13) Uani 1 1 d . . . . .
H5 H -0.006294 0.234016 0.608854 0.114 Uiso 1 1 calc R U . . .
C6 C 0.0919(2) 0.3379(2) 0.5387(4) 0.0765(9) Uani 1 1 d . . . . .
H6 H 0.108847 0.297897 0.471188 0.092 Uiso 1 1 calc R U . . .
C7 C 0.13383(17) 0.43683(17) 0.5613(3) 0.0523(5) Uani 1 1 d . . . . .
C8 C 0.20658(17) 0.49937(18) 0.4912(2) 0.0493(5) Uani 1 1 d . . . . .
C9 C 0.2866(2) 0.67933(19) 0.5171(3) 0.0579(6) Uani 1 1 d . . . . .
H9A H 0.264913 0.742764 0.555425 0.069 Uiso 1 1 calc R U . . .
H9AB H 0.268681 0.686883 0.423693 0.069 Uiso 1 1 calc R U . . .
C10 C 0.41209(19) 0.6638(2) 0.5579(2) 0.0548(6) Uani 1 1 d . . . . .
H10A H 0.450994 0.721987 0.527928 0.066 Uiso 1 1 calc R U . . .
H10B H 0.434119 0.601872 0.516665 0.066 Uiso 1 1 calc R U . . .
C11 C 0.44834(17) 0.65360(16) 0.7035(2) 0.0442(4) Uani 1 1 d . . . . .
H11A H 0.400827 0.602718 0.734961 0.053 Uiso 1 1 calc R U . . .
H11B H 0.436373 0.719357 0.743445 0.053 Uiso 1 1 calc R U . . .
C12 C 0.57078(17) 0.62188(16) 0.7466(2) 0.0428(4) Uani 1 1 d . . . . .
H12 H 0.582104 0.558239 0.699880 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6186(2) 0.82444(19) 0.7685(3) 0.0607(6) Uani 1 1 d . . . . .
C14 C 0.5941(2) 0.5960(2) 0.8903(2) 0.0604(6) Uani 1 1 d . . . . .
H14A H 0.601999 0.660379 0.938537 0.072 Uiso 1 1 calc R U . . .
H14B H 0.528864 0.560453 0.910709 0.072 Uiso 1 1 calc R U . . .
C15 C 0.6945(3) 0.5316(3) 0.9372(3) 0.0745(8) Uani 1 1 d . . . . .
N1 N 0.22189(14) 0.59348(14) 0.55609(18) 0.0451(4) Uani 1 1 d . . . . .
N2 N 0.5859(3) 0.89658(19) 0.8119(3) 0.0920(9) Uani 1 1 d . . . . .
O1 O 0.16444(17) 0.66948(16) 0.7312(2) 0.0739(6) Uani 1 1 d . . . . .
O2 O 0.24567(17) 0.47831(17) 0.3965(2) 0.0742(6) Uani 1 1 d . . . . .
F1 F 0.6993(2) 0.5031(2) 1.0590(2) 0.1314(10) Uani 1 1 d . . . . .
F2 F 0.79100(18) 0.5742(2) 0.9295(3) 0.1395(11) Uani 1 1 d . . . . .
F3 F 0.6953(3) 0.4450(2) 0.8714(3) 0.1421(11) Uani 1 1 d . . . . .
S1 S 0.66987(5) 0.71908(5) 0.70405(6) 0.0550(2) 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 O1 1.204(3) . ?
C1 N1 1.390(3) . ?
C1 C2 1.482(3) . ?
C2 C7 1.373(4) . ?
C2 C3 1.383(4) . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.485(3) . ?
C8 O2 1.207(3) . ?
C8 N1 1.390(3) . ?
C9 N1 1.459(3) . ?
C9 C10 1.514(3) . ?
C9 H9A 0.9700 . ?
C9 H9AB 0.9700 . ?
C10 C11 1.517(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.524(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C14 1.521(3) . ?
C12 S1 1.847(2) . ?
C12 H12 0.9800 . ?
C13 N2 1.140(4) . ?
C13 S1 1.688(3) . ?
C14 C15 1.480(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 F2 1.307(4) . ?
C15 F3 1.316(4) . ?
C15 F1 1.322(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
O1 C1 N1 124.8(2) . . ?
O1 C1 C2 129.0(2) . . ?
N1 C1 C2 106.13(19) . . ?
C7 C2 C3 121.9(3) . . ?
C7 C2 C1 108.0(2) . . ?
C3 C2 C1 130.0(3) . . ?
C4 C3 C2 116.9(4) . . ?
C4 C3 H3 121.6 . . ?
C2 C3 H3 121.6 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 117.2(3) . . ?
C7 C6 H6 121.4 . . ?
C5 C6 H6 121.4 . . ?
C2 C7 C6 120.9(3) . . ?
C2 C7 C8 108.4(2) . . ?
C6 C7 C8 130.7(3) . . ?
O2 C8 N1 124.3(2) . . ?
O2 C8 C7 129.9(2) . . ?
N1 C8 C7 105.78(19) . . ?
N1 C9 C10 112.41(19) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9AB 109.1 . . ?
C10 C9 H9AB 109.1 . . ?
H9A C9 H9AB 107.9 . . ?
C9 C10 C11 112.8(2) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 114.18(18) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C14 C12 C11 110.40(18) . . ?
C14 C12 S1 112.23(16) . . ?
C11 C12 S1 112.58(14) . . ?
C14 C12 H12 107.1 . . ?
C11 C12 H12 107.1 . . ?
S1 C12 H12 107.1 . . ?
N2 C13 S1 178.6(3) . . ?
C15 C14 C12 116.5(2) . . ?
C15 C14 H14A 108.2 . . ?
C12 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
C12 C14 H14B 108.2 . . ?
H14A C14 H14B 107.3 . . ?
F2 C15 F3 103.5(3) . . ?
F2 C15 F1 107.1(3) . . ?
F3 C15 F1 105.5(3) . . ?
F2 C15 C14 115.5(3) . . ?
F3 C15 C14 112.8(3) . . ?
F1 C15 C14 111.6(3) . . ?
C8 N1 C1 111.65(19) . . ?
C8 N1 C9 124.0(2) . . ?
C1 N1 C9 124.33(19) . . ?
C13 S1 C12 98.63(11) . . ?

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
O1 C1 C2 C7 -180.0(2) . . . . ?
N1 C1 C2 C7 0.1(2) . . . . ?
O1 C1 C2 C3 0.9(4) . . . . ?
N1 C1 C2 C3 -179.0(2) . . . . ?
C7 C2 C3 C4 0.2(4) . . . . ?
C1 C2 C3 C4 179.2(2) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C3 C2 C7 C6 -0.5(4) . . . . ?
C1 C2 C7 C6 -179.7(2) . . . . ?
C3 C2 C7 C8 178.8(2) . . . . ?
C1 C2 C7 C8 -0.3(2) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C5 C6 C7 C8 -178.9(2) . . . . ?
C2 C7 C8 O2 -178.6(2) . . . . ?
C6 C7 C8 O2 0.7(4) . . . . ?
C2 C7 C8 N1 0.5(2) . . . . ?
C6 C7 C8 N1 179.7(2) . . . . ?
N1 C9 C10 C11 -60.1(3) . . . . ?
C9 C10 C11 C12 171.31(19) . . . . ?
C10 C11 C12 C14 -170.4(2) . . . . ?
C10 C11 C12 S1 63.3(2) . . . . ?
C11 C12 C14 C15 160.0(2) . . . . ?
S1 C12 C14 C15 -73.5(3) . . . . ?
C12 C14 C15 F2 65.1(4) . . . . ?
C12 C14 C15 F3 -53.7(4) . . . . ?
C12 C14 C15 F1 -172.2(3) . . . . ?
O2 C8 N1 C1 178.7(2) . . . . ?
C7 C8 N1 C1 -0.4(2) . . . . ?
O2 C8 N1 C9 0.6(3) . . . . ?
C7 C8 N1 C9 -178.55(18) . . . . ?
O1 C1 N1 C8 -179.7(2) . . . . ?
C2 C1 N1 C8 0.3(2) . . . . ?
O1 C1 N1 C9 -1.6(3) . . . . ?
C2 C1 N1 C9 178.35(18) . . . . ?
C10 C9 N1 C8 -78.5(3) . . . . ?
C10 C9 N1 C1 103.6(3) . . . . ?
C14 C12 S1 C13 -73.43(19) . . . . ?
C11 C12 S1 C13 51.86(18) . . . . ?

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.051

