# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_A20272O_014
_database_code_depnum_ccdc_archive 'CCDC 2057463'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;Institute for Basic Science
South Korea
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-03-31 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         ?
_chemical_formula_sum            'C17 H20 Cl N O3 S'
_chemical_formula_weight         353.85

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'
Cl Cl 0.1484 0.1585 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.8411(2)
_cell_length_b                   15.3599(4)
_cell_length_c                   17.0637(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.7506(11)
_cell_angle_gamma                90
_cell_volume                     1761.56(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.09

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.349
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7026
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29939
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.324
_diffrn_reflns_theta_max         27.113
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3858
_reflns_number_gt                3357
_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       'Bruker APEX software'
_computing_cell_refinement       'Bruker APEX software'
_computing_data_reduction        'Bruker APEX software'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.7695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3858
_refine_ls_number_parameters     237
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.064
_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
Cl1 Cl 0.95386(7) 0.49686(3) 0.88681(2) 0.04639(14) Uani 1 1 d . . . . .
C2 C 0.7596(2) 0.49972(9) 0.80510(9) 0.0277(3) Uani 1 1 d . . . . .
C3 C 0.8034(2) 0.48318(10) 0.73046(9) 0.0298(3) Uani 1 1 d . . . . .
H3 H 0.935754 0.469927 0.724928 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6527(2) 0.48615(9) 0.66405(8) 0.0263(3) Uani 1 1 d . . . . .
H4 H 0.680327 0.475672 0.612341 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4602(2) 0.50468(8) 0.67418(8) 0.0206(3) Uani 1 1 d . . . . .
C6 C 0.4170(2) 0.52063(10) 0.74899(8) 0.0271(3) Uani 1 1 d . . . . .
H6 H 0.284252 0.532875 0.754753 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5689(2) 0.51860(10) 0.81559(9) 0.0313(3) Uani 1 1 d . . . . .
H7 H 0.542066 0.529970 0.867277 0.038 Uiso 1 1 calc R U . . .
S8 S 0.26927(5) 0.50926(2) 0.58890(2) 0.02053(10) Uani 1 1 d . . . . .
O9 O 0.08852(14) 0.53592(7) 0.61436(6) 0.0287(2) Uani 1 1 d . . . . .
O10 O 0.33847(15) 0.56075(6) 0.52895(6) 0.0272(2) Uani 1 1 d . . . . .
C12 C 0.2334(2) 0.40125(9) 0.55034(8) 0.0233(3) Uani 1 1 d . . . . .
H12A H 0.138918 0.403064 0.498801 0.028 Uiso 1 1 calc R U . . .
H12B H 0.361847 0.378883 0.539896 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1542(2) 0.33842(9) 0.60614(9) 0.0288(3) Uani 1 1 d . . . . .
H13 H 0.046(3) 0.3673(12) 0.6277(11) 0.043 Uiso 1 1 d . U . . .
C14 C 0.0688(2) 0.25707(9) 0.56146(9) 0.0282(3) Uani 1 1 d . . . . .
C15 C -0.1331(2) 0.24913(10) 0.53333(11) 0.0399(4) Uani 1 1 d . . . . .
H15 H -0.221491 0.294566 0.541420 0.048 Uiso 1 1 calc R U . . .
C16 C -0.2051(3) 0.17389(11) 0.49312(12) 0.0464(5) Uani 1 1 d . . . . .
H16 H -0.344385 0.169592 0.474014 0.056 Uiso 1 1 calc R U . . .
N17 N -0.0913(2) 0.10730(9) 0.47960(8) 0.0409(3) Uani 1 1 d . . . . .
C18 C 0.1029(3) 0.11592(10) 0.50725(10) 0.0369(4) Uani 1 1 d . . . . .
H18 H 0.187758 0.069368 0.498533 0.044 Uiso 1 1 calc R U . . .
C19 C 0.1892(2) 0.18852(10) 0.54797(9) 0.0324(3) Uani 1 1 d . . . . .
H19 H 0.329025 0.191121 0.566324 0.039 Uiso 1 1 calc R U . . .
O20 O 0.31655(18) 0.31988(7) 0.66806(6) 0.0375(3) Uani 1 1 d . . . . .
C21 C 0.2636(4) 0.27453(14) 0.73477(11) 0.0506(5) Uani 1 1 d . . . . .
H21A H 0.155(4) 0.3081(17) 0.7522(15) 0.076 Uiso 1 1 d . U . . .
H21B H 0.210(4) 0.2165(18) 0.7157(14) 0.076 Uiso 1 1 d . U . . .
C22 C 0.4434(4) 0.26968(15) 0.79969(12) 0.0530(7) Uani 0.882(5) 1 d . U P A 1
H22A H 0.408467 0.237349 0.845353 0.064 Uiso 0.882(5) 1 calc R U P A 1
H22B H 0.481831 0.329440 0.818133 0.064 Uiso 0.882(5) 1 calc R U P A 1
C23 C 0.6186(5) 0.22634(16) 0.77489(13) 0.0599(8) Uani 0.882(5) 1 d . U P A 1
H23A H 0.652141 0.258034 0.728641 0.072 Uiso 0.882(5) 1 calc R U P A 1
H23B H 0.580988 0.166194 0.757378 0.072 Uiso 0.882(5) 1 calc R U P A 1
C24 C 0.8028(13) 0.2230(4) 0.8410(4) 0.0703(19) Uani 0.882(5) 1 d . U P A 1
H24A H 0.910910 0.193371 0.821229 0.105 Uiso 0.882(5) 1 calc R U P A 1
H24B H 0.771522 0.191000 0.886812 0.105 Uiso 0.882(5) 1 calc R U P A 1
H24C H 0.844150 0.282341 0.857353 0.105 Uiso 0.882(5) 1 calc R U P A 1
C22B C 0.467(2) 0.2197(10) 0.7751(9) 0.033(4) Uiso 0.118(5) 1 d . . P A 2
H22C H 0.439437 0.185926 0.821316 0.040 Uiso 0.118(5) 1 calc R U P A 2
H22D H 0.500151 0.177834 0.735473 0.040 Uiso 0.118(5) 1 calc R U P A 2
C23B C 0.645(2) 0.2792(10) 0.8028(9) 0.034(4) Uiso 0.118(5) 1 d . . P A 2
H23C H 0.677901 0.307961 0.754879 0.041 Uiso 0.118(5) 1 calc R U P A 2
H23D H 0.602543 0.325459 0.836264 0.041 Uiso 0.118(5) 1 calc R U P A 2
C24B C 0.825(7) 0.243(3) 0.846(2) 0.044(7) Uani 0.118(5) 1 d . U P A 2
H24D H 0.936467 0.281515 0.842543 0.066 Uiso 0.118(5) 1 calc R U P A 2
H24E H 0.847877 0.185757 0.823737 0.066 Uiso 0.118(5) 1 calc R U P A 2
H24F H 0.813452 0.235799 0.902297 0.066 Uiso 0.118(5) 1 calc R U 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
Cl1 C2 1.7381(14) . ?
C2 C7 1.380(2) . ?
C2 C3 1.385(2) . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3887(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3850(19) . ?
C5 S8 1.7663(13) . ?
C6 C7 1.390(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
S8 O10 1.4411(10) . ?
S8 O9 1.4442(10) . ?
S8 C12 1.7847(13) . ?
C12 C13 1.5244(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O20 1.4117(18) . ?
C13 C14 1.522(2) . ?
C13 H13 0.993(19) . ?
C14 C15 1.381(2) . ?
C14 C19 1.382(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 N17 1.331(2) . ?
C16 H16 0.9500 . ?
N17 C18 1.331(2) . ?
C18 C19 1.386(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O20 C21 1.437(2) . ?
C21 C22 1.495(3) . ?
C21 C22B 1.662(15) . ?
C21 H21A 0.99(3) . ?
C21 H21B 0.99(3) . ?
C22 C23 1.499(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.527(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C22B C23B 1.53(2) . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
C23B C24B 1.42(5) . ?
C23B H23C 0.9900 . ?
C23B H23D 0.9900 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?

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
C7 C2 C3 121.98(13) . . ?
C7 C2 Cl1 120.08(11) . . ?
C3 C2 Cl1 117.95(12) . . ?
C4 C3 C2 119.42(14) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 118.93(13) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.44(13) . . ?
C6 C5 S8 119.99(11) . . ?
C4 C5 S8 118.57(10) . . ?
C5 C6 C7 119.58(13) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C6 118.65(13) . . ?
C2 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
O10 S8 O9 118.10(6) . . ?
O10 S8 C5 108.44(6) . . ?
O9 S8 C5 107.86(6) . . ?
O10 S8 C12 106.81(6) . . ?
O9 S8 C12 107.94(6) . . ?
C5 S8 C12 107.24(6) . . ?
C13 C12 S8 113.49(10) . . ?
C13 C12 H12A 108.9 . . ?
S8 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
S8 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
O20 C13 C14 112.59(12) . . ?
O20 C13 C12 105.88(12) . . ?
C14 C13 C12 110.78(12) . . ?
O20 C13 H13 110.5(11) . . ?
C14 C13 H13 108.0(11) . . ?
C12 C13 H13 109.0(11) . . ?
C15 C14 C19 117.62(14) . . ?
C15 C14 C13 120.80(14) . . ?
C19 C14 C13 121.58(14) . . ?
C14 C15 C16 119.04(16) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N17 C16 C15 124.11(16) . . ?
N17 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
C18 N17 C16 116.07(14) . . ?
N17 C18 C19 124.15(15) . . ?
N17 C18 H18 117.9 . . ?
C19 C18 H18 117.9 . . ?
C14 C19 C18 119.00(15) . . ?
C14 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C13 O20 C21 114.29(14) . . ?
O20 C21 C22 108.49(17) . . ?
O20 C21 C22B 105.0(5) . . ?
O20 C21 H21A 107.3(15) . . ?
C22 C21 H21A 111.2(14) . . ?
C22B C21 H21A 138.9(15) . . ?
O20 C21 H21B 107.8(14) . . ?
C22 C21 H21B 113.5(14) . . ?
C22B C21 H21B 84.8(15) . . ?
H21A C21 H21B 108(2) . . ?
C21 C22 C23 113.78(19) . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C23 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 C24 113.5(4) . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23B C22B C21 112.5(11) . . ?
C23B C22B H22C 109.1 . . ?
C21 C22B H22C 109.1 . . ?
C23B C22B H22D 109.1 . . ?
C21 C22B H22D 109.1 . . ?
H22C C22B H22D 107.8 . . ?
C24B C23B C22B 119(2) . . ?
C24B C23B H23C 107.5 . . ?
C22B C23B H23C 107.5 . . ?
C24B C23B H23D 107.5 . . ?
C22B C23B H23D 107.5 . . ?
H23C C23B H23D 107.0 . . ?
C23B C24B H24D 109.5 . . ?
C23B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C23B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?

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
C7 C2 C3 C4 0.5(2) . . . . ?
Cl1 C2 C3 C4 -179.10(11) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C3 C4 C5 S8 179.44(11) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
S8 C5 C6 C7 -178.71(11) . . . . ?
C3 C2 C7 C6 0.2(2) . . . . ?
Cl1 C2 C7 C6 179.81(12) . . . . ?
C5 C6 C7 C2 -0.6(2) . . . . ?
C6 C5 S8 O10 132.41(11) . . . . ?
C4 C5 S8 O10 -46.68(12) . . . . ?
C6 C5 S8 O9 3.43(13) . . . . ?
C4 C5 S8 O9 -175.65(11) . . . . ?
C6 C5 S8 C12 -112.59(12) . . . . ?
C4 C5 S8 C12 68.32(12) . . . . ?
O10 S8 C12 C13 -178.44(10) . . . . ?
O9 S8 C12 C13 -50.50(12) . . . . ?
C5 S8 C12 C13 65.48(12) . . . . ?
S8 C12 C13 O20 -74.72(13) . . . . ?
S8 C12 C13 C14 162.93(10) . . . . ?
O20 C13 C14 C15 144.05(15) . . . . ?
C12 C13 C14 C15 -97.60(17) . . . . ?
O20 C13 C14 C19 -35.54(19) . . . . ?
C12 C13 C14 C19 82.81(17) . . . . ?
C19 C14 C15 C16 -0.2(2) . . . . ?
C13 C14 C15 C16 -179.82(16) . . . . ?
C14 C15 C16 N17 0.2(3) . . . . ?
C15 C16 N17 C18 -0.1(3) . . . . ?
C16 N17 C18 C19 -0.1(3) . . . . ?
C15 C14 C19 C18 0.1(2) . . . . ?
C13 C14 C19 C18 179.69(14) . . . . ?
N17 C18 C19 C14 0.1(3) . . . . ?
C14 C13 O20 C21 -69.91(17) . . . . ?
C12 C13 O20 C21 168.90(14) . . . . ?
C13 O20 C21 C22 -172.65(15) . . . . ?
C13 O20 C21 C22B 153.3(6) . . . . ?
O20 C21 C22 C23 -57.3(2) . . . . ?
C21 C22 C23 C24 179.0(3) . . . . ?
O20 C21 C22B C23B 59.7(11) . . . . ?
C21 C22B C23B C24B 173(2) . . . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.040
























####################################################################### 
# 
# 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_A20275O_014
_database_code_depnum_ccdc_archive 'CCDC 2057471'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;Institute for Basic Science
South Korea
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-03-31 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         'C19 H14 F3 N O2 S'
_chemical_formula_sum            'C19 H14 F3 N O2 S'
_chemical_formula_weight         377.37

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                   15.1971(18)
_cell_length_b                   15.1809(16)
_cell_length_c                   7.5348(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.371(4)
_cell_angle_gamma                90
_cell_volume                     1724.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8719
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      26.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5838
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40338
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.1085
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.005
_diffrn_reflns_theta_max         26.474
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3551
_reflns_number_gt                3012
_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       'Bruker APEXIII'
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+11.5275P] 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         3551
_refine_ls_number_parameters     311
_refine_ls_number_restraints     421
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.1108
_refine_ls_wR_factor_ref         0.2055
_refine_ls_wR_factor_gt          0.1984
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.010
_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 0.8335(5) 0.4341(6) 1.1187(9) 0.0531(19) Uani 1 1 d . . . . .
H1A H 0.801341 0.469828 1.197645 0.080 Uiso 1 1 calc R U . . .
H1B H 0.887724 0.464878 1.096891 0.080 Uiso 1 1 calc R U . . .
H1C H 0.848971 0.377168 1.175598 0.080 Uiso 1 1 calc R U . . .
C2 C 0.7748(4) 0.4192(4) 0.9414(7) 0.0296(13) Uani 1 1 d . . . . .
C3 C 0.7985(4) 0.3579(4) 0.8193(8) 0.0322(13) Uani 1 1 d . . . . .
H3 H 0.850761 0.323882 0.848700 0.039 Uiso 1 1 calc R U . . .
C4 C 0.7480(3) 0.3455(4) 0.6574(7) 0.0252(11) Uani 1 1 d . . . . .
H4 H 0.765059 0.303297 0.575132 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6713(3) 0.3954(3) 0.6146(7) 0.0190(10) Uani 1 1 d . . . . .
C6 C 0.6454(3) 0.4555(3) 0.7363(7) 0.0229(11) Uani 1 1 d . . . . .
H6 H 0.592118 0.488215 0.708525 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6978(4) 0.4675(3) 0.8986(7) 0.0258(12) Uani 1 1 d . . . . .
H7 H 0.680798 0.509337 0.981498 0.031 Uiso 1 1 calc R U . . .
S8 S 0.60715(8) 0.38052(8) 0.40597(16) 0.0184(3) Uani 1 1 d . . . . .
O9 O 0.6627(2) 0.3417(3) 0.2880(5) 0.0277(9) Uani 1 1 d . . . . .
O10 O 0.5621(2) 0.4618(2) 0.3562(5) 0.0260(8) Uani 1 1 d . . . . .
C11 C 0.5253(3) 0.3011(3) 0.4430(6) 0.0156(10) Uani 1 1 d . . . . .
C12 C 0.5449(4) 0.2129(3) 0.4301(7) 0.0240(11) Uani 1 1 d . . . . .
H12 H 0.601490 0.193864 0.404931 0.029 Uiso 1 1 calc R U . . .
C13 C 0.4794(4) 0.1537(4) 0.4551(7) 0.0276(12) Uani 1 1 d . . . . .
H13 H 0.492851 0.092795 0.448515 0.033 Uiso 1 1 calc R U . . .
N14 N 0.3985(3) 0.1758(3) 0.4879(6) 0.0240(10) Uani 1 1 d . . . . .
C15 C 0.3794(3) 0.2623(3) 0.5003(6) 0.0193(10) Uani 1 1 d . . . . .
C16 C 0.4426(3) 0.3267(3) 0.4801(6) 0.0191(10) Uani 1 1 d . . . . .
H16 H 0.428911 0.387357 0.491651 0.023 Uiso 1 1 calc R U . . .
C17 C 0.2870(3) 0.2830(3) 0.5295(7) 0.0224(11) Uani 1 1 d . . . . .
C18 C 0.2546(4) 0.3686(4) 0.5174(8) 0.0332(13) Uani 1 1 d . . . . .
H18 H 0.293141 0.415463 0.495025 0.040 Uiso 1 1 calc R U . . .
C19 C 0.1675(4) 0.3869(5) 0.5374(9) 0.0400(15) Uani 1 1 d . . . . .
H19 H 0.146443 0.445870 0.526675 0.048 Uiso 1 1 calc R U . . .
C20 C 0.1111(4) 0.3206(4) 0.5725(8) 0.0320(13) Uani 1 1 d . . . . .
C21 C 0.1427(4) 0.2348(4) 0.5875(8) 0.0346(14) Uani 1 1 d . . . . .
H21 H 0.104116 0.188164 0.611228 0.042 Uiso 1 1 calc R U . . .
C22 C 0.2294(4) 0.2171(4) 0.5683(8) 0.0304(13) Uani 1 1 d . . . . .
H22 H 0.250513 0.158260 0.581793 0.036 Uiso 1 1 calc R U . . .
C23 C 0.0164(19) 0.3418(16) 0.593(4) 0.038(2) Uani 0.550(15) 1 d D U P A 1
F24 F -0.0225(6) 0.3918(11) 0.4626(14) 0.052(2) Uani 0.550(15) 1 d D U P A 1
F25 F 0.0133(7) 0.3880(9) 0.7505(16) 0.043(2) Uani 0.550(15) 1 d D U P A 1
F26 F -0.0331(6) 0.2700(6) 0.608(2) 0.045(2) Uani 0.550(15) 1 d D U P A 1
C23B C 0.020(6) 0.333(4) 0.604(11) 0.041(3) Uani 0.252(13) 1 d . U P A 2
F24B F -0.0320(12) 0.3422(18) 0.441(3) 0.049(3) Uani 0.252(13) 1 d . U P A 2
F25B F 0.0070(15) 0.4090(14) 0.685(3) 0.044(3) Uani 0.252(13) 1 d . U P A 2
F26B F -0.0196(15) 0.2698(15) 0.686(3) 0.047(3) Uani 0.252(13) 1 d . U P A 2
C23C C 0.016(2) 0.3489(17) 0.594(4) 0.042(3) Uani 0.197(13) 1 d D U P A 3
F24C F -0.0133(15) 0.4254(15) 0.527(4) 0.045(4) Uani 0.197(13) 1 d D U P A 3
F25C F 0.0110(18) 0.351(2) 0.776(2) 0.046(4) Uani 0.197(13) 1 d D U P A 3
F26C F -0.0413(17) 0.2867(16) 0.530(4) 0.047(4) Uani 0.197(13) 1 d D U P A 3


_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 1.525(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.383(8) . ?
C2 C3 1.388(8) . ?
C3 C4 1.368(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(7) . ?
C5 S8 1.755(5) . ?
C6 C7 1.383(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
S8 O9 1.430(4) . ?
S8 O10 1.438(4) . ?
S8 C11 1.780(5) . ?
C11 C16 1.377(7) . ?
C11 C12 1.378(7) . ?
C12 C13 1.371(8) . ?
C12 H12 0.9500 . ?
C13 N14 1.328(7) . ?
C13 H13 0.9500 . ?
N14 C15 1.351(6) . ?
C15 C16 1.393(7) . ?
C15 C17 1.483(7) . ?
C16 H16 0.9500 . ?
C17 C22 1.384(7) . ?
C17 C18 1.389(7) . ?
C18 C19 1.380(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.370(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(9) . ?
C20 C23B 1.44(8) . ?
C20 C23 1.50(3) . ?
C20 C23C 1.53(3) . ?
C21 C22 1.371(8) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 F24 1.32(2) . ?
C23 F26 1.34(3) . ?
C23 F25 1.38(3) . ?
C23B F25B 1.33(8) . ?
C23B F26B 1.33(8) . ?
C23B F24B 1.38(8) . ?
C23C F24C 1.32(2) . ?
C23C F26C 1.34(3) . ?
C23C F25C 1.38(3) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.9(5) . . ?
C7 C2 C1 120.5(6) . . ?
C3 C2 C1 120.6(6) . . ?
C4 C3 C2 121.4(5) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.4(5) . . ?
C6 C5 S8 120.3(4) . . ?
C4 C5 S8 119.3(4) . . ?
C7 C6 C5 119.4(5) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C2 120.7(5) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
O9 S8 O10 119.4(2) . . ?
O9 S8 C5 107.8(2) . . ?
O10 S8 C5 108.3(2) . . ?
O9 S8 C11 107.4(2) . . ?
O10 S8 C11 107.6(2) . . ?
C5 S8 C11 105.4(2) . . ?
C16 C11 C12 120.0(4) . . ?
C16 C11 S8 121.0(4) . . ?
C12 C11 S8 119.0(4) . . ?
C13 C12 C11 117.4(5) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
N14 C13 C12 124.4(5) . . ?
N14 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
C13 N14 C15 118.1(4) . . ?
N14 C15 C16 121.2(5) . . ?
N14 C15 C17 115.6(4) . . ?
C16 C15 C17 123.2(4) . . ?
C11 C16 C15 118.9(4) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C22 C17 C18 117.5(5) . . ?
C22 C17 C15 121.0(5) . . ?
C18 C17 C15 121.5(5) . . ?
C19 C18 C17 121.2(5) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 120.4(6) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 119.2(5) . . ?
C19 C20 C23B 125(3) . . ?
C21 C20 C23B 116(3) . . ?
C19 C20 C23 119.6(10) . . ?
C21 C20 C23 121.3(10) . . ?
C19 C20 C23C 115.7(11) . . ?
C21 C20 C23C 125.2(11) . . ?
C22 C21 C20 120.2(5) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 121.5(5) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
F24 C23 F26 109(2) . . ?
F24 C23 F25 106.6(18) . . ?
F26 C23 F25 105.1(19) . . ?
F24 C23 C20 112.8(19) . . ?
F26 C23 C20 113.0(17) . . ?
F25 C23 C20 109.6(19) . . ?
F25B C23B F26B 108(6) . . ?
F25B C23B F24B 103(4) . . ?
F26B C23B F24B 104(6) . . ?
F25B C23B C20 113(6) . . ?
F26B C23B C20 119(5) . . ?
F24B C23B C20 109(6) . . ?
F24C C23C F26C 108(2) . . ?
F24C C23C F25C 107(2) . . ?
F26C C23C F25C 105(2) . . ?
F24C C23C C20 119(2) . . ?
F26C C23C C20 110(2) . . ?
F25C C23C C20 107(2) . . ?

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
C7 C2 C3 C4 1.0(9) . . . . ?
C1 C2 C3 C4 -178.1(6) . . . . ?
C2 C3 C4 C5 0.0(9) . . . . ?
C3 C4 C5 C6 -1.5(8) . . . . ?
C3 C4 C5 S8 179.3(4) . . . . ?
C4 C5 C6 C7 2.0(7) . . . . ?
S8 C5 C6 C7 -178.7(4) . . . . ?
C5 C6 C7 C2 -1.0(8) . . . . ?
C3 C2 C7 C6 -0.5(8) . . . . ?
C1 C2 C7 C6 178.7(5) . . . . ?
C6 C5 S8 O9 159.4(4) . . . . ?
C4 C5 S8 O9 -21.4(5) . . . . ?
C6 C5 S8 O10 28.8(5) . . . . ?
C4 C5 S8 O10 -151.9(4) . . . . ?
C6 C5 S8 C11 -86.1(4) . . . . ?
C4 C5 S8 C11 93.1(4) . . . . ?
O9 S8 C11 C16 -151.0(4) . . . . ?
O10 S8 C11 C16 -21.2(4) . . . . ?
C5 S8 C11 C16 94.3(4) . . . . ?
O9 S8 C11 C12 27.5(4) . . . . ?
O10 S8 C11 C12 157.3(4) . . . . ?
C5 S8 C11 C12 -87.2(4) . . . . ?
C16 C11 C12 C13 0.1(7) . . . . ?
S8 C11 C12 C13 -178.4(4) . . . . ?
C11 C12 C13 N14 1.1(8) . . . . ?
C12 C13 N14 C15 -1.0(8) . . . . ?
C13 N14 C15 C16 -0.3(7) . . . . ?
C13 N14 C15 C17 177.5(4) . . . . ?
C12 C11 C16 C15 -1.3(7) . . . . ?
S8 C11 C16 C15 177.2(4) . . . . ?
N14 C15 C16 C11 1.4(7) . . . . ?
C17 C15 C16 C11 -176.2(4) . . . . ?
N14 C15 C17 C22 9.4(7) . . . . ?
C16 C15 C17 C22 -172.9(5) . . . . ?
N14 C15 C17 C18 -170.0(5) . . . . ?
C16 C15 C17 C18 7.8(8) . . . . ?
C22 C17 C18 C19 -2.1(9) . . . . ?
C15 C17 C18 C19 177.3(5) . . . . ?
C17 C18 C19 C20 1.0(10) . . . . ?
C18 C19 C20 C21 -0.1(9) . . . . ?
C18 C19 C20 C23B 177(4) . . . . ?
C18 C19 C20 C23 -179.8(14) . . . . ?
C18 C19 C20 C23C 179.4(14) . . . . ?
C19 C20 C21 C22 0.3(9) . . . . ?
C23B C20 C21 C22 -177(4) . . . . ?
C23 C20 C21 C22 -179.9(14) . . . . ?
C23C C20 C21 C22 -179.1(16) . . . . ?
C20 C21 C22 C17 -1.5(9) . . . . ?
C18 C17 C22 C21 2.4(8) . . . . ?
C15 C17 C22 C21 -177.0(5) . . . . ?
C19 C20 C23 F24 49(3) . . . . ?
C21 C20 C23 F24 -130.9(16) . . . . ?
C19 C20 C23 F26 173.3(14) . . . . ?
C21 C20 C23 F26 -6(3) . . . . ?
C19 C20 C23 F25 -69.8(18) . . . . ?
C21 C20 C23 F25 110.4(16) . . . . ?
C19 C20 C23B F25B -33(7) . . . . ?
C21 C20 C23B F25B 144(4) . . . . ?
C19 C20 C23B F26B -161(4) . . . . ?
C21 C20 C23B F26B 16(8) . . . . ?
C19 C20 C23B F24B 81(5) . . . . ?
C21 C20 C23B F24B -102(4) . . . . ?
C19 C20 C23C F24C 20(3) . . . . ?
C21 C20 C23C F24C -160(2) . . . . ?
C19 C20 C23C F26C 145.8(19) . . . . ?
C21 C20 C23C F26C -35(3) . . . . ?
C19 C20 C23C F25C -101(2) . . . . ?
C21 C20 C23C F25C 78(2) . . . . ?

_refine_diff_density_max         0.558
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.097
























