# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_AD371_KJ_OrthoP
_database_code_depnum_ccdc_archive 'CCDC 1990459'
loop_
_audit_author_name
_audit_author_address
'Ana de Bettencourt-Dias'
;University of Nevada, Reno
United States of America
;
_audit_update_record             
;
2020-03-14 deposited with the CCDC.	2020-04-29 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            'C23 H27 N3 O2 S2'
_chemical_formula_weight         441.59

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   7.6657(2)
_cell_length_b                   17.2855(5)
_cell_length_c                   17.1528(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2272.84(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      26.39

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.950
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6468
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS SHELXL-97 (Sheldrick, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19209
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.673
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4573
_reflns_number_gt                4451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.977

_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 SMART (Bruker, 2001)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 2001)'
_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)+(0.0595P)²+0.4712P] 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_abs_structure_details 
;
 Flack x determined using 2047 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4573
_refine_ls_number_parameters     276
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_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
S2 S 0.54344(7) 0.60131(4) 0.50337(4) 0.01767(16) Uani 1 1 d . . . A 1
C5 C 0.3419(3) 0.64559(15) 0.51500(14) 0.0164(5) Uani 1 1 d . . . A 1
C6 C 0.3256(3) 0.67619(17) 0.58860(15) 0.0186(5) Uani 1 1 d . . . A 1
H6 H 0.224570 0.702794 0.606160 0.022 Uiso 1 1 calc R U . A 1
C7 C 0.4748(3) 0.66397(16) 0.63545(16) 0.0174(5) Uani 1 1 d . . . A 1
H7 H 0.483960 0.681466 0.687797 0.021 Uiso 1 1 calc R U . A 1
C8 C 0.6046(3) 0.62450(16) 0.59797(15) 0.0155(5) Uani 1 1 d . . . A 1
C9 C 0.7700(3) 0.59605(15) 0.63109(15) 0.0157(5) Uani 1 1 d . . . A 1
C10 C 0.8516(3) 0.63645(16) 0.69170(14) 0.0160(5) Uani 1 1 d . . . A 1
H10 H 0.805813 0.684133 0.710132 0.019 Uiso 1 1 calc R U . A 1
C11 C 0.8461(3) 0.52727(16) 0.60591(14) 0.0164(5) Uani 1 1 d . . . A 1
H11 H 0.796143 0.499167 0.563875 0.020 Uiso 1 1 calc R U . A 1
C12 C 0.9960(3) 0.49990(15) 0.64272(14) 0.0147(5) Uani 1 1 d . . . A 1
C13 C 1.0023(3) 0.60461(15) 0.72425(14) 0.0144(5) Uani 1 1 d . . . A 1
C14 C 1.0593(3) 0.42080(16) 0.61953(14) 0.0152(5) Uani 1 1 d . . . A 1
C15 C 1.1001(3) 0.65223(15) 0.78488(14) 0.0150(5) Uani 1 1 d . . . A 1
C16 C 1.3742(3) 0.45474(16) 0.63875(16) 0.0197(5) Uani 1 1 d . . . A 1
H16A H 1.331215 0.508451 0.633019 0.024 Uiso 1 1 calc R U . A 1
H16B H 1.464353 0.446023 0.598378 0.024 Uiso 1 1 calc R U . A 1
C17 C 1.4566(4) 0.4456(2) 0.7188(2) 0.0297(7) Uani 1 1 d . . . A 1
H17A H 1.368820 0.455565 0.759055 0.045 Uiso 1 1 calc R U . A 1
H17B H 1.552796 0.482533 0.724328 0.045 Uiso 1 1 calc R U . A 1
H17C H 1.501383 0.392802 0.724493 0.045 Uiso 1 1 calc R U . A 1
C18 C 1.2726(3) 0.31952(16) 0.61048(15) 0.0197(5) Uani 1 1 d . . . A 1
H18A H 1.399635 0.315002 0.601094 0.024 Uiso 1 1 calc R U . A 1
H18B H 1.211615 0.302352 0.562646 0.024 Uiso 1 1 calc R U . A 1
C19 C 1.2221(4) 0.26674(17) 0.67742(16) 0.0233(6) Uani 1 1 d . . . A 1
H19A H 1.288327 0.281159 0.724092 0.035 Uiso 1 1 calc R U . A 1
H19B H 1.248448 0.213006 0.663512 0.035 Uiso 1 1 calc R U . A 1
H19C H 1.097020 0.271960 0.687911 0.035 Uiso 1 1 calc R U . A 1
C20 C 1.2110(4) 0.67000(19) 0.91554(16) 0.0269(6) Uani 1 1 d . . . A 1
H20A H 1.157012 0.662900 0.967485 0.032 Uiso 1 1 calc R U . A 1
H20B H 1.203227 0.725511 0.901754 0.032 Uiso 1 1 calc R U . A 1
C21 C 1.4017(5) 0.6458(3) 0.9189(2) 0.0472(10) Uani 1 1 d . . . A 1
H21A H 1.409448 0.591075 0.933540 0.071 Uiso 1 1 calc R U . A 1
H21B H 1.463056 0.677297 0.957646 0.071 Uiso 1 1 calc R U . A 1
H21C H 1.455439 0.653312 0.867597 0.071 Uiso 1 1 calc R U . A 1
C22 C 1.0265(4) 0.55436(19) 0.88509(16) 0.0272(6) Uani 1 1 d . . . A 1
H22A H 1.095652 0.530507 0.927485 0.033 Uiso 1 1 calc R U . A 1
H22B H 1.018725 0.516576 0.841850 0.033 Uiso 1 1 calc R U . A 1
C23 C 0.8442(5) 0.5720(2) 0.9149(2) 0.0408(9) Uani 1 1 d . . . A 1
H23A H 0.850595 0.612203 0.955081 0.061 Uiso 1 1 calc R U . A 1
H23B H 0.792935 0.525024 0.937125 0.061 Uiso 1 1 calc R U . A 1
H23C H 0.771496 0.590259 0.871618 0.061 Uiso 1 1 calc R U . A 1
N1 N 1.0746(3) 0.53779(13) 0.70197(12) 0.0153(4) Uani 1 1 d . . . A 1
N2 N 1.2292(3) 0.40112(13) 0.62561(12) 0.0163(5) Uani 1 1 d . . . A 1
N3 N 1.1156(3) 0.62396(14) 0.85761(12) 0.0185(5) Uani 1 1 d . . . A 1
O1 O 0.9479(2) 0.37400(12) 0.59679(12) 0.0207(4) Uani 1 1 d . . . A 1
O2 O 1.1611(3) 0.71453(12) 0.76440(10) 0.0231(4) Uani 1 1 d . . . A 1
S1A S 0.00619(13) 0.67302(7) 0.46563(7) 0.0273(3) Uani 0.800(3) 1 d D . P A 1
C1A C -0.0433(6) 0.6645(3) 0.3682(2) 0.0247(7) Uani 0.800(3) 1 d D . P A 1
H1A H -0.155470 0.674374 0.346826 0.030 Uiso 0.800(3) 1 calc R U P A 1
C2A C 0.0970(5) 0.6418(3) 0.3254(3) 0.0247(7) Uani 0.800(3) 1 d D . P A 1
H2A H 0.092770 0.632747 0.270757 0.030 Uiso 0.800(3) 1 calc R U P A 1
C3A C 0.2467(8) 0.6333(5) 0.3698(4) 0.0247(7) Uani 0.800(3) 1 d D . P A 1
H3A H 0.356387 0.618728 0.348583 0.030 Uiso 0.800(3) 1 calc R U P A 1
C4A C 0.2194(3) 0.64873(16) 0.45098(14) 0.0182(5) Uani 0.800(3) 1 d D . P A 1
S1B S 0.2711(7) 0.6300(5) 0.3617(4) 0.0273(3) Uani 0.200(3) 1 d D . P A 2
C1B C 0.055(2) 0.6507(14) 0.3308(14) 0.0247(7) Uani 0.200(3) 1 d D . P A 2
H1B H 0.018178 0.647428 0.278000 0.030 Uiso 0.200(3) 1 calc R U P A 2
C2B C -0.052(3) 0.6715(13) 0.3899(10) 0.0247(7) Uani 0.200(3) 1 d D . P A 2
H2B H -0.175439 0.673775 0.386632 0.030 Uiso 0.200(3) 1 calc R U P A 2
C3B C 0.046(2) 0.6892(14) 0.4569(11) 0.0247(7) Uani 0.200(3) 1 d D . P A 2
H3B H 0.008711 0.721233 0.498705 0.030 Uiso 0.200(3) 1 calc R U P A 2
C4B C 0.2194(3) 0.64873(16) 0.45098(14) 0.0182(5) Uani 0.200(3) 1 d D . 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
S2 C8 1.736(3) . ?
S2 C5 1.735(2) . ?
C5 C6 1.374(4) . ?
C5 C4A 1.446(3) . ?
C6 C7 1.414(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.367(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.474(3) . ?
C9 C11 1.393(4) . ?
C9 C10 1.400(4) . ?
C10 C13 1.396(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9500 . ?
C12 N1 1.351(3) . ?
C12 C14 1.505(4) . ?
C13 N1 1.337(3) . ?
C13 C15 1.524(3) . ?
C14 O1 1.239(3) . ?
C14 N2 1.350(3) . ?
C15 O2 1.225(3) . ?
C15 N3 1.345(3) . ?
C16 N2 1.465(3) . ?
C16 C17 1.519(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N2 1.472(4) . ?
C18 C19 1.517(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N3 1.468(3) . ?
C20 C21 1.522(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N3 1.462(4) . ?
C22 C23 1.519(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
S1A C4A 1.706(3) . ?
S1A C1A 1.720(4) . ?
C1A C2A 1.360(5) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.386(8) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.434(7) . ?
C3A H3A 0.9500 . ?
S1B C4B 1.614(7) . ?
S1B C1B 1.776(17) . ?
C1B C2B 1.352(18) . ?
C1B H1B 0.9500 . ?
C2B C3B 1.40(2) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.507(19) . ?
C3B H3B 0.9500 . ?

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
C8 S2 C5 91.77(12) . . ?
C6 C5 C4A 128.6(2) . . ?
C6 C5 S2 110.87(19) . . ?
C4A C5 S2 120.50(19) . . ?
C5 C6 C7 113.0(2) . . ?
C5 C6 H6 123.5 . . ?
C7 C6 H6 123.5 . . ?
C8 C7 C6 113.3(2) . . ?
C8 C7 H7 123.3 . . ?
C6 C7 H7 123.3 . . ?
C7 C8 C9 127.7(2) . . ?
C7 C8 S2 111.01(19) . . ?
C9 C8 S2 121.02(19) . . ?
C11 C9 C10 118.0(2) . . ?
C11 C9 C8 121.7(2) . . ?
C10 C9 C8 120.3(2) . . ?
C13 C10 C9 118.0(2) . . ?
C13 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C9 C11 C12 119.6(2) . . ?
C9 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
N1 C12 C11 123.0(2) . . ?
N1 C12 C14 119.7(2) . . ?
C11 C12 C14 117.0(2) . . ?
N1 C13 C10 124.7(2) . . ?
N1 C13 C15 117.2(2) . . ?
C10 C13 C15 117.9(2) . . ?
O1 C14 N2 121.6(3) . . ?
O1 C14 C12 117.0(2) . . ?
N2 C14 C12 121.3(2) . . ?
O2 C15 N3 123.5(2) . . ?
O2 C15 C13 117.8(2) . . ?
N3 C15 C13 118.7(2) . . ?
N2 C16 C17 112.9(2) . . ?
N2 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
N2 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 112.7(2) . . ?
N2 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N2 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
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 . . ?
N3 C20 C21 110.8(3) . . ?
N3 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C23 111.9(3) . . ?
N3 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
N3 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 N1 C12 116.7(2) . . ?
C14 N2 C16 125.8(2) . . ?
C14 N2 C18 116.5(2) . . ?
C16 N2 C18 117.5(2) . . ?
C15 N3 C22 123.9(2) . . ?
C15 N3 C20 118.3(2) . . ?
C22 N3 C20 117.4(2) . . ?
C4A S1A C1A 92.7(2) . . ?
C2A C1A S1A 112.0(4) . . ?
C2A C1A H1A 124.0 . . ?
S1A C1A H1A 124.0 . . ?
C1A C2A C3A 112.9(6) . . ?
C1A C2A H2A 123.6 . . ?
C3A C2A H2A 123.6 . . ?
C2A C3A C4A 113.2(6) . . ?
C2A C3A H3A 123.4 . . ?
C4A C3A H3A 123.4 . . ?
C3A C4A C5 129.5(3) . . ?
C3A C4A S1A 109.2(3) . . ?
C5 C4A S1A 121.32(19) . . ?
C4B S1B C1B 90.8(10) . . ?
C2B C1B S1B 113.2(18) . . ?
C2B C1B H1B 123.4 . . ?
S1B C1B H1B 123.4 . . ?
C1B C2B C3B 110.4(19) . . ?
C1B C2B H2B 124.8 . . ?
C3B C2B H2B 124.8 . . ?
C2B C3B C4B 108.3(16) . . ?
C2B C3B H3B 125.8 . . ?
C4B C3B H3B 125.8 . . ?
C3B C4B S1B 111.9(8) . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.060

