# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_korn1
_database_code_depnum_ccdc_archive 'CCDC 2022503'
loop_
_audit_author_name
_audit_author_address
'Khalil Abboud'
;University of Florida
United States of America
;
# end Validation Reply Form

_audit_update_record             
;
2020-08-10 deposited with the CCDC.	2020-09-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT201_korn1               
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 4 Report
RESPONSE: disordered atoms are refined with isotropic displacement parameters.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N3 O S2'
_chemical_formula_weight         371.51

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                   13.387(3)
_cell_length_b                   5.4878(11)
_cell_length_c                   24.641(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.130(6)
_cell_angle_gamma                90
_cell_volume                     1810.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.83

_exptl_crystal_description       needles
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   0.4874
_exptl_transmission_factor_max   0.5631
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.306
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_process_details   
'based on measured indexed crystal faces, Bruker SHELXTL2014 (Sheldrick, 2014)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            35779
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.521
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4153
_reflns_number_gt                3443
_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 APEX3 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'

_refine_special_details          
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and   
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C).
Methyl ones were allowed to rotate around the corresponding C---C.

The molecule has its end thiophene disordered and refined in two parts.  Their
 geometries are kept similar using a number of SADI commands.  Their SOF were
 fixed at 0.82 and 0.18 in the final cycles of refinements.  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0121P)²+4.0066P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4153
_refine_ls_number_parameters     217
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.003
_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
S1 S 0.12224(6) 1.07208(14) 0.51499(3) 0.01870(16) Uiso 0.82 1 d D . P A 1
C1 C 0.0918(3) 1.3184(6) 0.55303(16) 0.01870(16) Uiso 0.82 1 d D . P A 1
H1A H 0.0252 1.3739 0.5579 0.022 Uiso 0.82 1 calc R U P A 1
C2 C 0.17363(19) 1.4294(7) 0.57617(18) 0.01870(16) Uiso 0.82 1 d D . P A 1
H2A H 0.1702 1.5662 0.5997 0.022 Uiso 0.82 1 calc R U P A 1
C3 C 0.2627(3) 1.3152(6) 0.56058(14) 0.01870(16) Uiso 0.82 1 d D . P A 1
H3A H 0.3269 1.3689 0.5719 0.022 Uiso 0.82 1 calc R U P A 1
S1' S 0.2768(3) 1.3503(7) 0.56874(16) 0.0204(8) Uiso 0.18 1 d D . P A 2
C1' C 0.1549(5) 1.430(3) 0.5743(8) 0.0204(8) Uiso 0.18 1 d D . P A 2
H1'A H 0.1340 1.5736 0.5925 0.024 Uiso 0.18 1 calc R U P A 2
C2' C 0.0877(11) 1.270(3) 0.5502(7) 0.0204(8) Uiso 0.18 1 d D . P A 2
H2'A H 0.0180 1.2561 0.5567 0.024 Uiso 0.18 1 calc R U P A 2
C3' C 0.1455(4) 1.134(3) 0.5145(5) 0.0204(8) Uiso 0.18 1 d D . P A 2
H3'A H 0.1173 1.0575 0.4834 0.024 Uiso 0.18 1 calc R U P A 2
S2 S 0.20952(4) 0.64649(11) 0.44266(2) 0.01629(13) Uani 1 1 d . . . . .
O1 O 0.49238(12) 0.7089(3) 0.45706(8) 0.0249(4) Uani 1 1 d . . . . .
N1 N 0.37907(14) 0.4583(4) 0.41549(8) 0.0160(4) Uani 1 1 d . . . . .
N2 N 0.30801(17) -0.0851(4) 0.32019(10) 0.0286(5) Uani 1 1 d . . . . .
N3 N 0.03873(16) 0.2744(4) 0.38177(10) 0.0284(5) Uani 1 1 d . . . . .
C4 C 0.24753(15) 1.1148(4) 0.52669(9) 0.0163(5) Uani 1 1 d D . . . .
C5 C 0.32459(17) 0.9702(4) 0.50335(9) 0.0172(5) Uani 1 1 d . . . . .
H5A H 0.3907 1.0143 0.5135 0.021 Uiso 1 1 calc R U . . .
C6 C 0.31741(16) 0.7801(4) 0.46902(9) 0.0166(5) Uani 1 1 d . . . . .
C7 C 0.40627(17) 0.6552(4) 0.44827(9) 0.0177(5) Uani 1 1 d . . . . .
C8 C 0.27933(16) 0.4296(4) 0.40732(9) 0.0150(4) Uani 1 1 d . . . . .
C9 C 0.23039(17) 0.2595(4) 0.37687(9) 0.0170(5) Uani 1 1 d . . . . .
C10 C 0.27496(18) 0.0703(5) 0.34534(10) 0.0203(5) Uani 1 1 d . . . . .
C11 C 0.12365(18) 0.2638(4) 0.37841(10) 0.0200(5) Uani 1 1 d . . . . .
C12 C 0.45821(17) 0.3076(4) 0.39095(9) 0.0174(5) Uani 1 1 d . . . . .
H12A H 0.4363 0.1353 0.3903 0.021 Uiso 1 1 calc R U . . .
H12B H 0.5192 0.3178 0.4136 0.021 Uiso 1 1 calc R U . . .
C13 C 0.48266(17) 0.3891(4) 0.33353(9) 0.0193(5) Uani 1 1 d . . . . .
H13A H 0.5159 0.5502 0.3349 0.023 Uiso 1 1 calc R U . . .
H13B H 0.4198 0.4074 0.3127 0.023 Uiso 1 1 calc R U . . .
C14 C 0.55036(17) 0.2087(5) 0.30455(10) 0.0206(5) Uani 1 1 d . . . . .
H14A H 0.5525 0.2523 0.2656 0.025 Uiso 1 1 calc R U . . .
H14B H 0.5203 0.0444 0.3074 0.025 Uiso 1 1 calc R U . . .
C15 C 0.65698(17) 0.1966(5) 0.32595(10) 0.0205(5) Uani 1 1 d . . . . .
H15A H 0.6893 0.3573 0.3210 0.025 Uiso 1 1 calc R U . . .
H15B H 0.6556 0.1604 0.3653 0.025 Uiso 1 1 calc R U . . .
C16 C 0.71841(17) 0.0030(5) 0.29717(10) 0.0202(5) Uani 1 1 d . . . . .
H16A H 0.7134 0.0297 0.2575 0.024 Uiso 1 1 calc R U . . .
H16B H 0.6894 -0.1589 0.3051 0.024 Uiso 1 1 calc R U . . .
C17 C 0.82847(17) 0.0013(4) 0.31336(10) 0.0192(5) Uani 1 1 d . . . . .
H17A H 0.8597 0.1562 0.3017 0.023 Uiso 1 1 calc R U . . .
H17B H 0.8337 -0.0085 0.3534 0.023 Uiso 1 1 calc R U . . .
C18 C 0.88535(18) -0.2102(4) 0.28846(10) 0.0206(5) Uani 1 1 d . . . . .
H18A H 0.8787 -0.2021 0.2485 0.025 Uiso 1 1 calc R U . . .
H18B H 0.8547 -0.3649 0.3007 0.025 Uiso 1 1 calc R U . . .
C19 C 0.99586(18) -0.2126(5) 0.30326(10) 0.0230(5) Uani 1 1 d . . . . .
H19A H 1.0279 -0.3551 0.2868 0.034 Uiso 1 1 calc R U . . .
H19B H 1.0032 -0.2206 0.3428 0.034 Uiso 1 1 calc R U . . .
H19C H 1.0276 -0.0638 0.2897 0.034 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 C1 1.695(3) . ?
S1 C4 1.717(2) . ?
C1 C2 1.376(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.401(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.396(3) . ?
C3 H3A 0.9500 . ?
S1' C1' 1.695(6) . ?
S1' C4 1.702(3) . ?
C1' C2' 1.390(4) . ?
C1' H1'A 0.9500 . ?
C2' C3' 1.391(4) . ?
C2' H2'A 0.9500 . ?
C3' C4 1.402(4) . ?
C3' H3'A 0.9500 . ?
S2 C6 1.744(2) . ?
S2 C8 1.747(2) . ?
O1 C7 1.209(3) . ?
N1 C8 1.359(3) . ?
N1 C7 1.397(3) . ?
N1 C12 1.475(3) . ?
N2 C10 1.144(3) . ?
N3 C11 1.142(3) . ?
C4 C5 1.424(3) . ?
C5 C6 1.347(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.466(3) . ?
C8 C9 1.365(3) . ?
C9 C10 1.428(3) . ?
C9 C11 1.430(3) . ?
C12 C13 1.520(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.521(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.522(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.520(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.526(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.518(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.523(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 S1 C4 91.96(14) . . ?
C2 C1 S1 113.0(3) . . ?
C2 C1 H1A 123.5 . . ?
S1 C1 H1A 123.5 . . ?
C1 C2 C3 111.4(3) . . ?
C1 C2 H2A 124.3 . . ?
C3 C2 H2A 124.3 . . ?
C4 C3 C2 113.2(3) . . ?
C4 C3 H3A 123.4 . . ?
C2 C3 H3A 123.4 . . ?
C1' S1' C4 91.4(5) . . ?
C2' C1' S1' 115.1(11) . . ?
C2' C1' H1'A 122.4 . . ?
S1' C1' H1'A 122.4 . . ?
C1' C2' C3' 104.4(14) . . ?
C1' C2' H2'A 127.8 . . ?
C3' C2' H2'A 127.8 . . ?
C2' C3' C4 116.5(11) . . ?
C2' C3' H3'A 121.7 . . ?
C4 C3' H3'A 121.7 . . ?
C6 S2 C8 91.63(11) . . ?
C8 N1 C7 115.47(19) . . ?
C8 N1 C12 125.50(19) . . ?
C7 N1 C12 118.97(18) . . ?
C3 C4 C5 125.2(2) . . ?
C3' C4 C5 131.4(6) . . ?
C3' C4 S1' 107.3(6) . . ?
C5 C4 S1' 120.2(2) . . ?
C3 C4 S1 110.40(19) . . ?
C5 C4 S1 124.37(16) . . ?
C6 C5 C4 129.4(2) . . ?
C6 C5 H5A 115.3 . . ?
C4 C5 H5A 115.3 . . ?
C5 C6 C7 121.6(2) . . ?
C5 C6 S2 128.13(18) . . ?
C7 C6 S2 110.23(17) . . ?
O1 C7 N1 122.6(2) . . ?
O1 C7 C6 126.7(2) . . ?
N1 C7 C6 110.65(19) . . ?
N1 C8 C9 129.1(2) . . ?
N1 C8 S2 111.95(17) . . ?
C9 C8 S2 118.92(17) . . ?
C8 C9 C10 126.6(2) . . ?
C8 C9 C11 116.9(2) . . ?
C10 C9 C11 116.5(2) . . ?
N2 C10 C9 177.9(3) . . ?
N3 C11 C9 176.7(3) . . ?
N1 C12 C13 111.91(19) . . ?
N1 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N1 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 112.05(19) . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 115.2(2) . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C16 C15 C14 112.1(2) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 113.9(2) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 112.6(2) . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C19 113.4(2) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         1.113
_refine_diff_density_min         -1.241
_refine_diff_density_rms         0.070

