# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2194939'
loop_
_audit_author_name
_audit_author_address
'Shouhei Katao'
;Nara Institute of Science and Technology (NAIST)
Japan
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_audit_creation_date             2021-09-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H9 P S2'
_chemical_formula_sum            'C17 H9 P S2'
_chemical_formula_weight         308.33
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.6391(6)
_cell_length_b                   3.90201(15)
_cell_length_c                   23.5802(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.7137(12)
_cell_angle_gamma                90
_cell_volume                     1327.64(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11242
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14081
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.408
_diffrn_reflns_theta_max         24.408
_diffrn_reflns_theta_min         2.429
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Rigaku curved IP area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'Imaging plate area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku VariMax RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              'MicroMax 007'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1790
_reflns_number_total             2190
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0545P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1084
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C16(H16), C3(H3), C5(H5), C9(H9), C4(H4), C15(H15), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.95724(4) 0.13433(17) 0.58166(3) 0.0269(2) Uani 1 1 d . . . . .
S2 S 0.78740(5) 0.67764(18) 0.37455(3) 0.0272(2) Uani 1 1 d . . . . .
P1 P 0.68024(5) 0.54417(18) 0.53330(3) 0.0250(2) Uani 1 1 d . . . . .
C6 C 0.80521(17) 0.2400(6) 0.62396(12) 0.0228(6) Uani 1 1 d . . . . .
C7 C 0.78540(17) 0.3678(6) 0.56518(12) 0.0214(6) Uani 1 1 d . . . . .
C2 C 0.92709(19) -0.0410(6) 0.69254(12) 0.0268(7) Uani 1 1 d . . . . .
H2 H 0.987831 -0.133408 0.701666 0.032 Uiso 1 1 calc R U . . .
C11 C 0.70311(17) 0.6293(6) 0.46499(12) 0.0214(6) Uani 1 1 d . . . . .
C12 C 0.63765(17) 0.7876(6) 0.41902(12) 0.0232(6) Uani 1 1 d . . . . .
C16 C 0.62076(19) 0.9688(7) 0.31869(12) 0.0287(7) Uani 1 1 d . . . . .
H16 H 0.645599 0.991998 0.284178 0.034 Uiso 1 1 calc R U . . .
C1 C 0.89518(18) 0.1030(6) 0.63827(12) 0.0245(7) Uani 1 1 d . . . . .
C3 C 0.86830(18) -0.0446(7) 0.73202(12) 0.0291(7) Uani 1 1 d . . . . .
H3 H 0.888805 -0.140957 0.768976 0.035 Uiso 1 1 calc R U . . .
C5 C 0.74721(19) 0.2323(7) 0.66556(12) 0.0276(7) Uani 1 1 d . . . . .
H5 H 0.686348 0.324266 0.657080 0.033 Uiso 1 1 calc R U . . .
C10 C 0.78834(17) 0.5569(6) 0.44635(12) 0.0231(6) Uani 1 1 d . . . . .
C9 C 0.86463(18) 0.4064(6) 0.48025(12) 0.0249(6) Uani 1 1 d . . . . .
H9 H 0.919010 0.362187 0.464444 0.030 Uiso 1 1 calc R U . . .
C4 C 0.77900(19) 0.0902(7) 0.71906(12) 0.0302(7) Uani 1 1 d . . . . .
H4 H 0.739597 0.084435 0.747192 0.036 Uiso 1 1 calc R U . . .
C17 C 0.67315(18) 0.8249(6) 0.36813(12) 0.0248(6) Uani 1 1 d . . . . .
C15 C 0.53148(19) 1.0762(7) 0.32174(13) 0.0302(7) Uani 1 1 d . . . . .
H15 H 0.494401 1.173126 0.288684 0.036 Uiso 1 1 calc R U . . .
C13 C 0.54648(17) 0.8973(6) 0.42095(12) 0.0269(7) Uani 1 1 d . . . . .
H13 H 0.520631 0.870591 0.455032 0.032 Uiso 1 1 calc R U . . .
C8 C 0.86194(17) 0.3207(6) 0.53677(12) 0.0233(6) Uani 1 1 d . . . . .
C14 C 0.49523(18) 1.0447(7) 0.37232(12) 0.0286(7) Uani 1 1 d . . . . .
H14 H 0.434375 1.125557 0.373539 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 1.741(3) . ?
S1 C8 1.760(3) . ?
S2 C10 1.755(3) . ?
S2 C17 1.751(3) . ?
P1 C7 1.737(3) . ?
P1 C11 1.732(3) . ?
C6 C7 1.455(4) . ?
C6 C1 1.409(4) . ?
C6 C5 1.402(4) . ?
C7 C8 1.411(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.404(4) . ?
C2 C3 1.370(4) . ?
C11 C12 1.458(4) . ?
C11 C10 1.420(4) . ?
C12 C17 1.393(4) . ?
C12 C13 1.410(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.400(4) . ?
C16 C15 1.386(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.385(4) . ?
C10 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.381(4) . ?
C4 H4 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(3) . ?
C14 H14 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
C1 S1 C8 91.54(13) . . ?
C17 S2 C10 91.34(13) . . ?
C11 P1 C7 100.50(12) . . ?
C1 C6 C7 112.7(2) . . ?
C5 C6 C7 128.8(2) . . ?
C5 C6 C1 118.5(3) . . ?
C6 C7 P1 124.57(19) . . ?
C8 C7 P1 124.2(2) . . ?
C8 C7 C6 111.2(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C3 C2 C1 118.2(3) . . ?
C12 C11 P1 124.5(2) . . ?
C10 C11 P1 124.6(2) . . ?
C10 C11 C12 110.8(2) . . ?
C17 C12 C11 113.0(2) . . ?
C17 C12 C13 119.3(2) . . ?
C13 C12 C11 127.7(3) . . ?
C17 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
C15 C16 C17 117.8(3) . . ?
C6 C1 S1 112.2(2) . . ?
C2 C1 S1 126.2(2) . . ?
C2 C1 C6 121.6(3) . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.3(3) . . ?
C4 C3 H3 119.3 . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.1 . . ?
C11 C10 S2 112.4(2) . . ?
C9 C10 S2 122.9(2) . . ?
C9 C10 C11 124.7(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C12 C17 S2 112.4(2) . . ?
C12 C17 C16 121.8(2) . . ?
C16 C17 S2 125.8(2) . . ?
C16 C15 H15 119.4 . . ?
C16 C15 C14 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 H13 120.6 . . ?
C7 C8 S1 112.4(2) . . ?
C9 C8 S1 122.1(2) . . ?
C9 C8 C7 125.5(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 H14 119.5 . . ?

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
S2 C10 C9 C8 179.14(19) . . . . ?
P1 C7 C8 S1 -179.84(13) . . . . ?
P1 C7 C8 C9 0.0(4) . . . . ?
P1 C11 C12 C17 -179.53(18) . . . . ?
P1 C11 C12 C13 -0.2(4) . . . . ?
P1 C11 C10 S2 -179.87(13) . . . . ?
P1 C11 C10 C9 0.4(4) . . . . ?
C6 C7 C8 S1 -1.5(3) . . . . ?
C6 C7 C8 C9 178.3(2) . . . . ?
C6 C5 C4 C3 0.2(4) . . . . ?
C7 P1 C11 C12 -179.1(2) . . . . ?
C7 P1 C11 C10 0.4(2) . . . . ?
C7 C6 C1 S1 1.1(3) . . . . ?
C7 C6 C1 C2 -178.5(2) . . . . ?
C7 C6 C5 C4 178.3(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C11 P1 C7 C6 -178.6(2) . . . . ?
C11 P1 C7 C8 -0.6(2) . . . . ?
C11 C12 C17 S2 -1.1(3) . . . . ?
C11 C12 C17 C16 179.4(2) . . . . ?
C11 C12 C13 C14 179.6(2) . . . . ?
C11 C10 C9 C8 -1.2(4) . . . . ?
C12 C11 C10 S2 -0.3(3) . . . . ?
C12 C11 C10 C9 179.9(2) . . . . ?
C12 C13 C14 C15 1.8(4) . . . . ?
C16 C15 C14 C13 -1.5(4) . . . . ?
C1 S1 C8 C7 1.9(2) . . . . ?
C1 S1 C8 C9 -177.9(2) . . . . ?
C1 C6 C7 P1 178.55(18) . . . . ?
C1 C6 C7 C8 0.3(3) . . . . ?
C1 C6 C5 C4 -0.4(4) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C3 C2 C1 S1 -179.8(2) . . . . ?
C3 C2 C1 C6 -0.2(4) . . . . ?
C5 C6 C7 P1 -0.2(4) . . . . ?
C5 C6 C7 C8 -178.5(3) . . . . ?
C5 C6 C1 S1 -180.0(2) . . . . ?
C5 C6 C1 C2 0.4(4) . . . . ?
C10 S2 C17 C12 0.8(2) . . . . ?
C10 S2 C17 C16 -179.8(2) . . . . ?
C10 C11 C12 C17 0.9(3) . . . . ?
C10 C11 C12 C13 -179.7(2) . . . . ?
C10 C9 C8 S1 -179.24(19) . . . . ?
C10 C9 C8 C7 1.0(4) . . . . ?
C17 S2 C10 C11 -0.2(2) . . . . ?
C17 S2 C10 C9 179.5(2) . . . . ?
C17 C12 C13 C14 -1.1(4) . . . . ?
C17 C16 C15 C14 0.5(4) . . . . ?
C15 C16 C17 S2 -179.1(2) . . . . ?
C15 C16 C17 C12 0.3(4) . . . . ?
C13 C12 C17 S2 179.45(18) . . . . ?
C13 C12 C17 C16 0.0(4) . . . . ?
C8 S1 C1 C6 -1.7(2) . . . . ?
C8 S1 C1 C2 177.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2194940'
loop_
_audit_author_name
_audit_author_address
'Shouhei Katao'
;Nara Institute of Science and Technology (NAIST)
Japan
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H10 S2'
_chemical_formula_sum            'C18 H10 S2'
_chemical_formula_weight         290.38
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   26.5674(11)
_cell_length_b                   3.90265(14)
_cell_length_c                   12.4158(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1287.32(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16216
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18872
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.067
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Rigaku curved IP area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'Imaging plate area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku VariMax RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              'MicroMax 007'
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2678
_reflns_number_total             2917
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 1121 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+0.5709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1081
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C1(H1), C5(H5), C10(H10), C6(H6), C16(H16), C15(H15),
 C14(H14), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.45396(4) 0.5955(3) 0.69711(8) 0.0216(2) Uani 1 1 d . . . . .
S2 S 0.65952(4) 0.3608(3) 0.63639(8) 0.0236(3) Uani 1 1 d . . . . .
C3 C 0.42378(16) 0.7885(11) 0.5871(3) 0.0211(9) Uani 1 1 d . . . . .
C8 C 0.45734(15) 0.8736(10) 0.5042(3) 0.0194(8) Uani 1 1 d . . . . .
C4 C 0.37220(16) 0.8575(11) 0.5788(4) 0.0243(9) Uani 1 1 d . . . . .
H4 H 0.349773 0.798964 0.635437 0.029 Uiso 1 1 calc R U . . .
C9 C 0.50873(16) 0.7658(11) 0.5277(3) 0.0198(8) Uani 1 1 d . . . . .
C7 C 0.43885(16) 1.0349(11) 0.4117(3) 0.0212(9) Uani 1 1 d . . . . .
H7 H 0.461156 1.096361 0.355072 0.025 Uiso 1 1 calc R U . . .
C1 C 0.55729(16) 0.4831(11) 0.6710(3) 0.0234(9) Uani 1 1 d . . . . .
H1 H 0.559397 0.381763 0.740460 0.028 Uiso 1 1 calc R U . . .
C5 C 0.35479(16) 1.0125(12) 0.4862(4) 0.0244(9) Uani 1 1 d . . . . .
H5 H 0.319838 1.057859 0.478675 0.029 Uiso 1 1 calc R U . . .
C2 C 0.51216(15) 0.6129(10) 0.6308(3) 0.0195(8) Uani 1 1 d . . . . .
C10 C 0.55124(15) 0.7874(11) 0.4629(3) 0.0206(9) Uani 1 1 d . . . . .
H10 H 0.549345 0.892111 0.393906 0.025 Uiso 1 1 calc R U . . .
C6 C 0.38795(16) 1.1044(11) 0.4029(3) 0.0242(9) Uani 1 1 d . . . . .
H6 H 0.375350 1.214882 0.340288 0.029 Uiso 1 1 calc R U . . .
C18 C 0.59914(16) 0.5099(11) 0.6039(4) 0.0217(9) Uani 1 1 d . . . . .
C11 C 0.59667(15) 0.6538(10) 0.5000(3) 0.0194(8) Uani 1 1 d . . . . .
C12 C 0.64503(16) 0.6392(10) 0.4453(4) 0.0211(9) Uani 1 1 d . . . . .
C16 C 0.73157(17) 0.4442(11) 0.4732(4) 0.0281(10) Uani 1 1 d . . . . .
H16 H 0.756576 0.344839 0.518133 0.034 Uiso 1 1 calc R U . . .
C15 C 0.74297(17) 0.5480(11) 0.3697(4) 0.0275(10) Uani 1 1 d . . . . .
H15 H 0.776202 0.518490 0.343039 0.033 Uiso 1 1 calc R U . . .
C17 C 0.68244(16) 0.4889(11) 0.5101(3) 0.0237(9) Uani 1 1 d . . . . .
C14 C 0.70632(17) 0.6957(12) 0.3038(4) 0.0283(10) Uani 1 1 d . . . . .
H14 H 0.714799 0.764465 0.232684 0.034 Uiso 1 1 calc R U . . .
C13 C 0.65769(16) 0.7427(12) 0.3413(4) 0.0237(9) Uani 1 1 d . . . . .
H13 H 0.633019 0.845212 0.296274 0.028 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 C3 1.754(4) . ?
S1 C2 1.753(4) . ?
S2 C18 1.753(4) . ?
S2 C17 1.754(5) . ?
C3 C8 1.401(6) . ?
C3 C4 1.400(6) . ?
C8 C9 1.458(6) . ?
C8 C7 1.400(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(6) . ?
C9 C2 1.416(6) . ?
C9 C10 1.390(6) . ?
C7 H7 0.9500 . ?
C7 C6 1.384(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.394(6) . ?
C1 C18 1.394(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.394(6) . ?
C6 H6 0.9500 . ?
C18 C11 1.408(6) . ?
C11 C12 1.455(6) . ?
C12 C17 1.407(6) . ?
C12 C13 1.393(6) . ?
C16 H16 0.9500 . ?
C16 C15 1.381(7) . ?
C16 C17 1.395(6) . ?
C15 H15 0.9500 . ?
C15 C14 1.397(7) . ?
C14 H14 0.9500 . ?
C14 C13 1.386(6) . ?
C13 H13 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
C2 S1 C3 91.2(2) . . ?
C18 S2 C17 91.0(2) . . ?
C8 C3 S1 112.5(3) . . ?
C4 C3 S1 126.0(3) . . ?
C4 C3 C8 121.5(4) . . ?
C3 C8 C9 112.4(4) . . ?
C7 C8 C3 119.1(4) . . ?
C7 C8 C9 128.5(4) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 H4 120.8 . . ?
C2 C9 C8 111.3(4) . . ?
C10 C9 C8 128.9(4) . . ?
C10 C9 C2 119.8(4) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.7(4) . . ?
C6 C7 H7 120.1 . . ?
C2 C1 H1 121.8 . . ?
C18 C1 H1 121.8 . . ?
C18 C1 C2 116.4(4) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C9 C2 S1 112.6(3) . . ?
C1 C2 S1 125.2(3) . . ?
C1 C2 C9 122.2(4) . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.3(4) . . ?
C11 C10 H10 120.3 . . ?
C7 C6 C5 120.3(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C1 C18 S2 124.6(3) . . ?
C1 C18 C11 122.7(4) . . ?
C11 C18 S2 112.7(3) . . ?
C10 C11 C18 119.5(4) . . ?
C10 C11 C12 128.7(4) . . ?
C18 C11 C12 111.8(4) . . ?
C17 C12 C11 111.9(4) . . ?
C13 C12 C11 129.4(4) . . ?
C13 C12 C17 118.7(4) . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.3(4) . . ?
C17 C16 H16 120.8 . . ?
C16 C15 H15 119.5 . . ?
C16 C15 C14 120.9(4) . . ?
C14 C15 H15 119.5 . . ?
C12 C17 S2 112.7(3) . . ?
C16 C17 S2 125.7(3) . . ?
C16 C17 C12 121.7(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 C15 120.5(5) . . ?
C13 C14 H14 119.7 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13 120.1 . . ?

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
S1 C3 C8 C9 2.8(5) . . . . ?
S1 C3 C8 C7 -179.0(3) . . . . ?
S1 C3 C4 C5 179.8(3) . . . . ?
S2 C18 C11 C10 -179.3(3) . . . . ?
S2 C18 C11 C12 0.6(5) . . . . ?
C3 S1 C2 C9 0.6(3) . . . . ?
C3 S1 C2 C1 -177.3(4) . . . . ?
C3 C8 C9 C2 -2.3(5) . . . . ?
C3 C8 C9 C10 175.9(4) . . . . ?
C3 C8 C7 C6 -0.6(6) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
C8 C3 C4 C5 0.1(6) . . . . ?
C8 C9 C2 S1 0.8(4) . . . . ?
C8 C9 C2 C1 178.8(4) . . . . ?
C8 C9 C10 C11 -177.2(4) . . . . ?
C8 C7 C6 C5 -0.3(6) . . . . ?
C4 C3 C8 C9 -177.5(4) . . . . ?
C4 C3 C8 C7 0.8(6) . . . . ?
C4 C5 C6 C7 1.2(7) . . . . ?
C9 C8 C7 C6 177.3(4) . . . . ?
C9 C10 C11 C18 -2.1(6) . . . . ?
C9 C10 C11 C12 178.0(4) . . . . ?
C7 C8 C9 C2 179.7(4) . . . . ?
C7 C8 C9 C10 -2.2(7) . . . . ?
C1 C18 C11 C10 2.3(7) . . . . ?
C1 C18 C11 C12 -177.8(4) . . . . ?
C2 S1 C3 C8 -2.0(3) . . . . ?
C2 S1 C3 C4 178.3(4) . . . . ?
C2 C9 C10 C11 0.8(6) . . . . ?
C2 C1 C18 S2 -179.3(3) . . . . ?
C2 C1 C18 C11 -1.1(7) . . . . ?
C10 C9 C2 S1 -177.5(3) . . . . ?
C10 C9 C2 C1 0.5(6) . . . . ?
C10 C11 C12 C17 179.1(4) . . . . ?
C10 C11 C12 C13 -2.6(7) . . . . ?
C18 S2 C17 C12 -0.3(3) . . . . ?
C18 S2 C17 C16 -178.6(4) . . . . ?
C18 C1 C2 S1 177.4(3) . . . . ?
C18 C1 C2 C9 -0.3(6) . . . . ?
C18 C11 C12 C17 -0.8(5) . . . . ?
C18 C11 C12 C13 177.6(4) . . . . ?
C11 C12 C17 S2 0.6(5) . . . . ?
C11 C12 C17 C16 179.1(4) . . . . ?
C11 C12 C13 C14 -178.1(4) . . . . ?
C16 C15 C14 C13 0.3(7) . . . . ?
C15 C16 C17 S2 177.5(3) . . . . ?
C15 C16 C17 C12 -0.8(6) . . . . ?
C15 C14 C13 C12 -0.6(7) . . . . ?
C17 S2 C18 C1 178.1(4) . . . . ?
C17 S2 C18 C11 -0.2(3) . . . . ?
C17 C12 C13 C14 0.2(6) . . . . ?
C17 C16 C15 C14 0.3(7) . . . . ?
C13 C12 C17 S2 -177.9(3) . . . . ?
C13 C12 C17 C16 0.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
