# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_Pbca_a
_database_code_depnum_ccdc_archive 'CCDC 1963994'
loop_
_audit_author_name
_audit_author_address
'lingbing ge'
;University of Electronic Science and Technology of China
China
;
_audit_update_record             
;
2020-03-19 deposited with the CCDC.	2022-08-02 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            'C32 H24 N2 O2 S2'
_chemical_formula_weight         532.65

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   14.187(3)
_cell_length_b                   13.429(4)
_cell_length_c                   27.488(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5237(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    4381
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.70

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             2224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59227
_diffrn_reflns_av_unetI/netI     0.0893
_diffrn_reflns_av_R_equivalents  0.1795
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.063
_diffrn_reflns_theta_max         28.560
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6608
_reflns_number_gt                3646
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0668P)²+5.6444P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0062(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6608
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1837
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
S1 S 0.54567(6) 0.64926(8) 0.50681(3) 0.0396(3) Uani 1 1 d . . . . .
C1 C 0.78820(19) 0.4546(2) 0.75773(11) 0.0221(6) Uani 1 1 d . . . . .
N1 N 0.55509(16) 0.4734(2) 0.70579(9) 0.0263(6) Uani 1 1 d . . . . .
H1 H 0.502435 0.460054 0.721406 0.032 Uiso 1 1 calc R U . . .
O1 O 0.87417(13) 0.46524(19) 0.76001(8) 0.0317(5) Uani 1 1 d . . . . .
S2 S 0.57066(9) 0.69759(9) 0.88494(4) 0.0607(4) Uani 1 1 d . . . . .
C2 C 0.72878(18) 0.4778(2) 0.71624(10) 0.0202(6) Uani 1 1 d . . . . .
N2 N 0.71151(17) 0.6998(2) 0.67995(9) 0.0264(6) Uani 1 1 d . . . . .
H2 H 0.701826 0.754419 0.662971 0.032 Uiso 1 1 calc R U . . .
O2 O 0.84223(14) 0.38444(17) 0.63417(8) 0.0283(5) Uani 1 1 d . . . . .
C7 C 0.6709(2) 0.3828(3) 0.87795(12) 0.0292(7) Uani 1 1 d . . . . .
H7 H 0.683179 0.366104 0.910942 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7462(2) 0.4013(2) 0.84626(11) 0.0269(7) Uani 1 1 d . . . . .
H6 H 0.809597 0.398747 0.857395 0.032 Uiso 1 1 calc R U . . .
C5 C 0.72582(19) 0.4233(2) 0.79870(10) 0.0224(6) Uani 1 1 d . . . . .
C4 C 0.63289(19) 0.4287(2) 0.78218(10) 0.0213(6) Uani 1 1 d . . . . .
C3 C 0.63608(18) 0.4606(2) 0.73000(10) 0.0203(6) Uani 1 1 d . . . . .
C8 C 0.5791(2) 0.3885(3) 0.86165(11) 0.0289(7) Uani 1 1 d . . . . .
H8 H 0.528914 0.375960 0.883716 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5583(2) 0.4124(2) 0.81300(11) 0.0253(7) Uani 1 1 d . . . . .
H9 H 0.495041 0.417128 0.801885 0.030 Uiso 1 1 calc R U . . .
C10 C 0.76660(18) 0.5252(2) 0.67251(10) 0.0211(6) Uani 1 1 d . . . . .
C11 C 0.81984(18) 0.4738(2) 0.63561(11) 0.0215(6) Uani 1 1 d . . . . .
C12 C 0.83909(19) 0.5465(2) 0.59547(11) 0.0230(6) Uani 1 1 d . . . . .
C13 C 0.79579(19) 0.6367(2) 0.60809(11) 0.0229(6) Uani 1 1 d . . . . .
C14 C 0.75416(19) 0.6232(2) 0.65730(10) 0.0212(6) Uani 1 1 d . . . . .
C15 C 0.7964(2) 0.7159(3) 0.57632(12) 0.0291(7) Uani 1 1 d . . . . .
H15 H 0.765588 0.776623 0.584249 0.035 Uiso 1 1 calc R U . . .
C16 C 0.8436(2) 0.7044(3) 0.53206(12) 0.0329(8) Uani 1 1 d . . . . .
H16 H 0.845187 0.758456 0.509759 0.040 Uiso 1 1 calc R U . . .
C17 C 0.8879(2) 0.6162(3) 0.52001(12) 0.0344(8) Uani 1 1 d . . . . .
H17 H 0.920446 0.610924 0.489902 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8855(2) 0.5341(3) 0.55185(11) 0.0305(7) Uani 1 1 d . . . . .
H18 H 0.914694 0.472677 0.543606 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6809(2) 0.6993(2) 0.72928(12) 0.0277(7) Uani 1 1 d . . . . .
C20 C 0.7425(2) 0.6750(2) 0.76634(11) 0.0307(7) Uani 1 1 d . . . . .
H20 H 0.806344 0.659962 0.759003 0.037 Uiso 1 1 calc R U . . .
C21 C 0.7115(3) 0.6725(3) 0.81452(12) 0.0345(8) Uani 1 1 d . . . . .
H21 H 0.754056 0.654992 0.839773 0.041 Uiso 1 1 calc R U . . .
C22 C 0.6183(3) 0.6955(3) 0.82563(13) 0.0393(9) Uani 1 1 d . . . . .
C23 C 0.5577(3) 0.7231(3) 0.78824(15) 0.0442(9) Uani 1 1 d . . . . .
H23 H 0.494538 0.741057 0.795557 0.053 Uiso 1 1 calc R U . . .
C24 C 0.5885(2) 0.7248(3) 0.74040(14) 0.0374(8) Uani 1 1 d . . . . .
H24 H 0.546369 0.743503 0.715161 0.045 Uiso 1 1 calc R U . . .
C25 C 0.6637(4) 0.6490(4) 0.92233(15) 0.0725(16) Uani 1 1 d . . . . .
H25A H 0.680268 0.581894 0.911273 0.109 Uiso 1 1 calc R U . . .
H25B H 0.642512 0.646221 0.956240 0.109 Uiso 1 1 calc R U . . .
H25C H 0.718994 0.692422 0.919883 0.109 Uiso 1 1 calc R U . . .
C26 C 0.54732(18) 0.5067(2) 0.65699(11) 0.0227(6) Uani 1 1 d . . . . .
C27 C 0.4894(2) 0.5868(3) 0.64603(12) 0.0292(7) Uani 1 1 d . . . . .
H27 H 0.449779 0.614302 0.670454 0.035 Uiso 1 1 calc R U . . .
C28 C 0.4890(2) 0.6269(3) 0.59965(12) 0.0315(7) Uani 1 1 d . . . . .
H28 H 0.449274 0.681906 0.592506 0.038 Uiso 1 1 calc R U . . .
C29 C 0.5463(2) 0.5873(3) 0.56335(11) 0.0289(7) Uani 1 1 d . . . . .
C30 C 0.5984(2) 0.5016(3) 0.57350(11) 0.0271(7) Uani 1 1 d . . . . .
H30 H 0.634046 0.470612 0.548477 0.032 Uiso 1 1 calc R U . . .
C31 C 0.59822(19) 0.4616(2) 0.61996(11) 0.0246(6) Uani 1 1 d . . . . .
H31 H 0.633237 0.402825 0.626505 0.030 Uiso 1 1 calc R U . . .
C32 C 0.6305(2) 0.5826(3) 0.47151(12) 0.0413(9) Uani 1 1 d . . . . .
H32A H 0.633793 0.611443 0.438798 0.062 Uiso 1 1 calc R U . . .
H32B H 0.611706 0.512551 0.469217 0.062 Uiso 1 1 calc R U . . .
H32C H 0.692382 0.587333 0.487134 0.062 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 C29 1.763(3) . ?
S1 C32 1.786(4) . ?
C1 O1 1.230(3) . ?
C1 C2 1.452(4) . ?
C1 C5 1.493(4) . ?
N1 C3 1.339(4) . ?
N1 C26 1.418(4) . ?
N1 H1 0.8800 . ?
S2 C22 1.765(4) . ?
S2 C25 1.795(6) . ?
C2 C3 1.388(4) . ?
C2 C10 1.462(4) . ?
N2 C14 1.347(4) . ?
N2 C19 1.424(4) . ?
N2 H2 0.8800 . ?
O2 C11 1.243(4) . ?
C7 C8 1.380(4) . ?
C7 C6 1.401(4) . ?
C7 H7 0.9500 . ?
C6 C5 1.371(4) . ?
C6 H6 0.9500 . ?
C5 C4 1.396(4) . ?
C4 C9 1.373(4) . ?
C4 C3 1.498(4) . ?
C8 C9 1.407(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C14 1.392(4) . ?
C10 C11 1.441(4) . ?
C11 C12 1.498(4) . ?
C12 C18 1.378(4) . ?
C12 C13 1.401(4) . ?
C13 C15 1.377(4) . ?
C13 C14 1.487(4) . ?
C15 C16 1.397(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.409(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.381(4) . ?
C19 C24 1.388(4) . ?
C20 C21 1.396(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(6) . ?
C23 C24 1.386(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.387(4) . ?
C26 C31 1.387(4) . ?
C27 C28 1.384(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.393(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.396(5) . ?
C30 C31 1.385(4) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
C29 S1 C32 103.83(17) . . ?
O1 C1 C2 126.2(3) . . ?
O1 C1 C5 125.6(3) . . ?
C2 C1 C5 108.0(2) . . ?
C3 N1 C26 125.3(2) . . ?
C3 N1 H1 117.4 . . ?
C26 N1 H1 117.4 . . ?
C22 S2 C25 104.0(2) . . ?
C3 C2 C1 107.5(2) . . ?
C3 C2 C10 130.1(3) . . ?
C1 C2 C10 121.7(2) . . ?
C14 N2 C19 125.0(3) . . ?
C14 N2 H2 117.5 . . ?
C19 N2 H2 117.5 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C5 C6 C7 118.0(3) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 C1 130.9(3) . . ?
C4 C5 C1 107.4(2) . . ?
C9 C4 C5 121.3(3) . . ?
C9 C4 C3 131.3(3) . . ?
C5 C4 C3 107.3(2) . . ?
N1 C3 C2 131.0(3) . . ?
N1 C3 C4 119.1(2) . . ?
C2 C3 C4 109.7(2) . . ?
C7 C8 C9 121.3(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 117.5(3) . . ?
C4 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
C14 C10 C11 107.9(3) . . ?
C14 C10 C2 127.7(3) . . ?
C11 C10 C2 124.3(3) . . ?
O2 C11 C10 128.3(3) . . ?
O2 C11 C12 124.0(3) . . ?
C10 C11 C12 107.6(3) . . ?
C18 C12 C13 122.0(3) . . ?
C18 C12 C11 130.5(3) . . ?
C13 C12 C11 107.5(2) . . ?
C15 C13 C12 120.5(3) . . ?
C15 C13 C14 132.3(3) . . ?
C12 C13 C14 107.1(3) . . ?
N2 C14 C10 129.8(3) . . ?
N2 C14 C13 120.4(3) . . ?
C10 C14 C13 109.8(3) . . ?
C13 C15 C16 118.0(3) . . ?
C13 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 121.5(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C12 C18 C17 117.2(3) . . ?
C12 C18 H18 121.4 . . ?
C17 C18 H18 121.4 . . ?
C20 C19 C24 119.5(3) . . ?
C20 C19 N2 120.7(3) . . ?
C24 C19 N2 119.8(3) . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 118.9(3) . . ?
C23 C22 S2 116.2(3) . . ?
C21 C22 S2 124.8(3) . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C19 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
S2 C25 H25A 109.5 . . ?
S2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
S2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C31 119.2(3) . . ?
C27 C26 N1 119.8(3) . . ?
C31 C26 N1 121.0(3) . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 120.6(3) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C30 118.7(3) . . ?
C28 C29 S1 116.7(3) . . ?
C30 C29 S1 124.6(3) . . ?
C31 C30 C29 120.2(3) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C26 120.5(3) . . ?
C30 C31 H31 119.7 . . ?
C26 C31 H31 119.7 . . ?
S1 C32 H32A 109.5 . . ?
S1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
S1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_CHENGDU_NEUTRAL_0m
_database_code_depnum_ccdc_archive 'CCDC 1991442'
loop_
_audit_author_name
_audit_author_address
'lingbing ge'
;University of Electronic Science and Technology of China
China
;
_audit_update_record             
;
2020-03-19 deposited with the CCDC.	2022-08-02 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            'C32 H24 N2 O2 S2'
_chemical_formula_weight         532.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   4.880(3)
_cell_length_b                   10.531(6)
_cell_length_c                   12.724(7)
_cell_angle_alpha                105.72(2)
_cell_angle_beta                 91.51(2)
_cell_angle_gamma                99.05(3)
_cell_volume                     620.0(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    178(2)
_cell_measurement_reflns_used    366
_cell_measurement_theta_min      28.84
_cell_measurement_theta_max      67.75

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             278
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.224
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4008
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      178(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6684
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.618
_diffrn_reflns_theta_max         65.036
_diffrn_reflns_theta_full        65.036
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2098
_reflns_number_gt                1551
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0800P)²+2.2000P] 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         2098
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0987
_refine_ls_wR_factor_ref         0.2482
_refine_ls_wR_factor_gt          0.2318
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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
S1 S 0.8065(3) 0.86319(18) 0.03736(14) 0.0729(6) Uani 1 1 d . . . . .
O1 O 0.1383(8) 0.6231(4) 0.7155(3) 0.0632(10) Uani 1 1 d . . . . .
N1 N 0.2751(9) 0.5727(5) 0.3408(4) 0.0609(12) Uani 1 1 d . . . . .
H1A H 0.163469 0.496921 0.308941 0.073 Uiso 1 1 calc R U . . .
C1 C 0.9321(10) 0.8794(6) 0.5753(5) 0.0608(15) Uani 1 1 d . . . . .
H1 H 1.092671 0.932402 0.559046 0.073 Uiso 1 1 calc R U . . .
C2 C 0.8807(11) 0.8917(6) 0.6817(5) 0.0619(14) Uani 1 1 d . . . . .
H2 H 1.002426 0.953806 0.738568 0.074 Uiso 1 1 calc R U . . .
C3 C 0.6466(11) 0.8123(6) 0.7076(5) 0.0601(14) Uani 1 1 d . . . . .
H3 H 0.608123 0.818465 0.781420 0.072 Uiso 1 1 calc R U . . .
C4 C 0.4783(10) 0.7267(6) 0.6232(5) 0.0541(13) Uani 1 1 d . . . . .
C5 C 0.5244(10) 0.7145(6) 0.5146(5) 0.0535(13) Uani 1 1 d . . . . .
C6 C 0.7563(10) 0.7912(6) 0.4893(5) 0.0582(14) Uani 1 1 d . . . . .
H6 H 0.794930 0.784100 0.415340 0.070 Uiso 1 1 calc R U . . .
C9 C 0.2246(10) 0.6277(6) 0.6259(4) 0.0526(12) Uani 1 1 d . . . . .
C8 C 0.1241(10) 0.5541(5) 0.5169(4) 0.0501(12) Uani 1 1 d . . . . .
C7 C 0.2993(10) 0.6088(6) 0.4484(5) 0.0545(13) Uani 1 1 d . . . . .
C10 C 0.4100(11) 0.6430(6) 0.2707(5) 0.0586(14) Uani 1 1 d . . . . .
C11 C 0.3758(11) 0.7719(6) 0.2755(5) 0.0623(15) Uani 1 1 d . . . . .
H11 H 0.266060 0.817124 0.329074 0.075 Uiso 1 1 calc R U . . .
C12 C 0.4990(11) 0.8356(6) 0.2033(5) 0.0616(14) Uani 1 1 d . . . . .
H12 H 0.474615 0.924565 0.207679 0.074 Uiso 1 1 calc R U . . .
C13 C 0.6585(10) 0.7708(6) 0.1244(5) 0.0582(14) Uani 1 1 d . . . . .
C14 C 0.6863(11) 0.6401(6) 0.1171(5) 0.0621(15) Uani 1 1 d . . . . .
H14 H 0.790911 0.593931 0.061908 0.074 Uiso 1 1 calc R U . . .
C15 C 0.5624(11) 0.5762(6) 0.1899(5) 0.0617(14) Uani 1 1 d . . . . .
H15 H 0.581911 0.486307 0.184380 0.074 Uiso 1 1 calc R U . . .
C16 C 1.0069(13) 0.7532(8) -0.0455(6) 0.0773(19) Uani 1 1 d . . . . .
H00A H 1.098449 0.795902 -0.097865 0.116 Uiso 1 1 calc R U . . .
H00E H 0.884715 0.669945 -0.085339 0.116 Uiso 1 1 calc R U . . .
H16 H 1.147976 0.733215 0.001006 0.116 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 C13 1.760(5) . ?
S1 C16 1.777(7) . ?
O1 C9 1.236(6) . ?
N1 C7 1.314(7) . ?
N1 C10 1.419(7) . ?
N1 H1A 0.8800 . ?
C1 C2 1.359(8) . ?
C1 C6 1.395(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.407(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.355(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(8) . ?
C4 C9 1.495(7) . ?
C5 C6 1.382(7) . ?
C5 C7 1.488(8) . ?
C6 H6 0.9500 . ?
C9 C8 1.423(8) . ?
C8 C7 1.408(7) . ?
C8 C8 1.491(10) 2_566 ?
C10 C11 1.379(9) . ?
C10 C15 1.385(8) . ?
C11 C12 1.374(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(9) . ?
C14 C15 1.384(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H00A 0.9800 . ?
C16 H00E 0.9800 . ?
C16 H16 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
C13 S1 C16 103.1(3) . . ?
C7 N1 C10 126.9(5) . . ?
C7 N1 H1A 116.6 . . ?
C10 N1 H1A 116.6 . . ?
C2 C1 C6 122.0(5) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C1 C2 C3 119.9(6) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 117.5(5) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 123.4(5) . . ?
C3 C4 C9 129.2(5) . . ?
C5 C4 C9 107.3(5) . . ?
C6 C5 C4 119.0(5) . . ?
C6 C5 C7 134.1(5) . . ?
C4 C5 C7 106.9(4) . . ?
C5 C6 C1 118.2(5) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
O1 C9 C8 131.7(5) . . ?
O1 C9 C4 118.8(5) . . ?
C8 C9 C4 109.4(4) . . ?
C7 C8 C9 105.8(5) . . ?
C7 C8 C8 127.4(6) . 2_566 ?
C9 C8 C8 126.8(6) . 2_566 ?
N1 C7 C8 126.0(5) . . ?
N1 C7 C5 123.4(5) . . ?
C8 C7 C5 110.5(5) . . ?
C11 C10 C15 119.3(5) . . ?
C11 C10 N1 121.8(5) . . ?
C15 C10 N1 118.7(6) . . ?
C12 C11 C10 120.6(6) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.4(6) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.2(5) . . ?
C14 C13 S1 124.7(4) . . ?
C12 C13 S1 116.1(5) . . ?
C13 C14 C15 120.3(6) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.1(6) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
S1 C16 H00A 109.5 . . ?
S1 C16 H00E 109.5 . . ?
H00A C16 H00E 109.5 . . ?
S1 C16 H16 109.5 . . ?
H00A C16 H16 109.5 . . ?
H00E C16 H16 109.5 . . ?

_refine_diff_density_max         0.673
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.110

