# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_falck4_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2038759'
loop_
_audit_author_name
_audit_author_address
'Muhammed Yousufuddin' 'University of North Texas at Dallas'
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H25 N O3 S'
_chemical_formula_sum            'C20 H25 N O3 S'
_chemical_formula_weight         359.47

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'

_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                   9.3481(14)
_cell_length_b                   11.8624(17)
_cell_length_c                   17.695(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.756(4)
_cell_angle_gamma                90
_cell_volume                     1927.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      31.90

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.662
_exptl_crystal_size_mid          0.367
_exptl_crystal_size_min          0.186
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28839
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.196
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5885
_reflns_number_gt                4278
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²] 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         5885
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1804
_refine_ls_wR_factor_gt          0.1623
_refine_ls_goodness_of_fit_ref   1.248
_refine_ls_restrained_S_all      1.248
_refine_ls_shift/su_max          0.055
_refine_ls_shift/su_mean         0.001

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
S1 S 0.27716(4) 0.55136(3) 0.19779(2) 0.04609(14) Uani 1 1 d . . . . .
O1 O 0.24363(14) 0.62215(9) 0.25754(7) 0.0657(4) Uani 1 1 d . . . . .
O2 O 0.32079(14) 0.60246(11) 0.13219(7) 0.0691(4) Uani 1 1 d . . . . .
O3 O 0.25525(11) 0.30653(10) 0.30144(6) 0.0551(3) Uani 1 1 d . . . . .
N1 N 0.40863(12) 0.46831(9) 0.23641(7) 0.0397(3) Uani 1 1 d . . . . .
C1 C 0.12300(14) 0.46881(11) 0.16148(8) 0.0394(3) Uani 1 1 d . . . . .
C2 C 0.02545(16) 0.43915(14) 0.20868(8) 0.0500(4) Uani 1 1 d . . . . .
H2 H 0.0399 0.4641 0.2594 0.060 Uiso 1 1 calc R U . . .
C3 C -0.09287(16) 0.37233(15) 0.17955(9) 0.0541(4) Uani 1 1 d . . . . .
H3 H -0.1571 0.3518 0.2114 0.065 Uiso 1 1 calc R U . . .
C4 C -0.11841(15) 0.33494(13) 0.10367(9) 0.0484(3) Uani 1 1 d . . . . .
C5 C -0.02047(16) 0.36604(13) 0.05773(8) 0.0468(3) Uani 1 1 d . . . . .
H5 H -0.0355 0.3418 0.0069 0.056 Uiso 1 1 calc R U . . .
C6 C 0.09968(15) 0.43255(12) 0.08590(8) 0.0431(3) Uani 1 1 d . . . . .
H6 H 0.1643 0.4527 0.0541 0.052 Uiso 1 1 calc R U . . .
C7 C -0.2486(2) 0.26444(19) 0.07171(13) 0.0735(5) Uani 1 1 d . . . . .
H7A H -0.2849 0.2291 0.1132 0.110 Uiso 1 1 calc R U . . .
H7B H -0.2213 0.2076 0.0385 0.110 Uiso 1 1 calc R U . . .
H7C H -0.3230 0.3114 0.0430 0.110 Uiso 1 1 calc R U . . .
C8 C 0.44048(14) 0.44455(10) 0.32008(8) 0.0370(3) Uani 1 1 d . . . . .
H8 H 0.3803 0.4960 0.3441 0.044 Uiso 1 1 calc R U . . .
C9 C 0.40032(14) 0.32479(12) 0.34037(8) 0.0415(3) Uani 1 1 d . . . . .
H9 H 0.4653 0.2708 0.3218 0.050 Uiso 1 1 calc R U . . .
C10 C 0.41063(18) 0.31001(15) 0.42637(9) 0.0563(4) Uani 1 1 d . . . . .
H10A H 0.3523 0.3672 0.4455 0.068 Uiso 1 1 calc R U . . .
H10B H 0.5109 0.3194 0.4523 0.068 Uiso 1 1 calc R U . . .
C11 C 0.3568(2) 0.19344(16) 0.44380(10) 0.0629(5) Uani 1 1 d . . . . .
H11A H 0.4231 0.1365 0.4312 0.075 Uiso 1 1 calc R U . . .
H11B H 0.3546 0.1875 0.4982 0.075 Uiso 1 1 calc R U . . .
C12 C 0.20539(19) 0.17314(17) 0.39732(11) 0.0656(5) Uani 1 1 d . . . . .
H12A H 0.1763 0.0959 0.4041 0.079 Uiso 1 1 calc R U . . .
H12B H 0.1362 0.2226 0.4153 0.079 Uiso 1 1 calc R U . . .
C13 C 0.2049(2) 0.19543(16) 0.31310(11) 0.0692(5) Uani 1 1 d . . . . .
H13A H 0.2669 0.1408 0.2942 0.083 Uiso 1 1 calc R U . . .
H13B H 0.1068 0.1863 0.2840 0.083 Uiso 1 1 calc R U . . .
C14 C 0.59906(14) 0.47528(11) 0.35136(8) 0.0392(3) Uani 1 1 d . . . . .
C15 C 0.63204(19) 0.58691(15) 0.36943(11) 0.0643(5) Uani 1 1 d . . . . .
H15 H 0.5576 0.6399 0.3647 0.077 Uiso 1 1 calc R U . . .
C16 C 0.7744(2) 0.62033(18) 0.39439(15) 0.0871(7) Uani 1 1 d . . . . .
H16 H 0.7948 0.6959 0.4056 0.104 Uiso 1 1 calc R U . . .
C17 C 0.8854(2) 0.54465(19) 0.40284(12) 0.0740(6) Uani 1 1 d . . . . .
H17 H 0.9808 0.5680 0.4201 0.089 Uiso 1 1 calc R U . . .
C18 C 0.85508(19) 0.43362(19) 0.38573(12) 0.0697(5) Uani 1 1 d . . . . .
H18 H 0.9304 0.3813 0.3910 0.084 Uiso 1 1 calc R U . . .
C19 C 0.71211(16) 0.39865(14) 0.36046(10) 0.0559(4) Uani 1 1 d . . . . .
H19 H 0.6925 0.3229 0.3496 0.067 Uiso 1 1 calc R U . . .
C20 C 0.47384(19) 0.39660(15) 0.18569(10) 0.0580(4) Uani 1 1 d . . . . .
H20A H 0.5677 0.3715 0.2120 0.087 Uiso 1 1 calc R U . . .
H20B H 0.4847 0.4383 0.1406 0.087 Uiso 1 1 calc R U . . .
H20C H 0.4123 0.3325 0.1709 0.087 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
S1 O1 1.4301(12) . ?
S1 O2 1.4346(12) . ?
S1 N1 1.6231(11) . ?
S1 C1 1.7615(14) . ?
O3 C9 1.4184(16) . ?
O3 C13 1.4275(19) . ?
N1 C20 1.4508(19) . ?
N1 C8 1.4818(17) . ?
C1 C6 1.383(2) . ?
C1 C2 1.392(2) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(2) . ?
C4 C7 1.498(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C14 1.5266(17) . ?
C8 C9 1.5292(18) . ?
C8 H8 0.9800 . ?
C9 C10 1.517(2) . ?
C9 H9 0.9800 . ?
C10 C11 1.523(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.518(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.513(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.380(2) . ?
C14 C15 1.383(2) . ?
C15 C16 1.380(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.358(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 O2 118.99(8) . . ?
O1 S1 N1 107.36(6) . . ?
O2 S1 N1 106.85(7) . . ?
O1 S1 C1 108.59(7) . . ?
O2 S1 C1 106.06(7) . . ?
N1 S1 C1 108.65(6) . . ?
C9 O3 C13 112.47(12) . . ?
C20 N1 C8 118.51(11) . . ?
C20 N1 S1 117.91(10) . . ?
C8 N1 S1 122.09(9) . . ?
C6 C1 C2 119.93(13) . . ?
C6 C1 S1 119.75(11) . . ?
C2 C1 S1 120.31(11) . . ?
C3 C2 C1 119.36(14) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.64(14) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.96(14) . . ?
C5 C4 C7 120.48(15) . . ?
C3 C4 C7 121.55(14) . . ?
C4 C5 C6 121.40(13) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.70(13) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C14 108.50(10) . . ?
N1 C8 C9 113.51(11) . . ?
C14 C8 C9 113.64(11) . . ?
N1 C8 H8 106.9 . . ?
C14 C8 H8 106.9 . . ?
C9 C8 H8 106.9 . . ?
O3 C9 C10 110.21(11) . . ?
O3 C9 C8 106.40(11) . . ?
C10 C9 C8 111.74(12) . . ?
O3 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
C8 C9 H9 109.5 . . ?
C9 C10 C11 110.28(14) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 110.14(14) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 109.72(14) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O3 C13 C12 111.31(15) . . ?
O3 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
O3 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C19 C14 C15 118.07(14) . . ?
C19 C14 C8 123.75(12) . . ?
C15 C14 C8 118.15(13) . . ?
C16 C15 C14 120.59(18) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 121.08(18) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.30(17) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C19 120.30(19) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 120.65(16) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4



