# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
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data_pro83_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2126128'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold '
;Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California
United States of America
;
_audit_update_record             
;
2021-12-03 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
_audit_creation_date             2017-06-02
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 N P S2'
_chemical_formula_sum            'C15 H10 N P S2'
_chemical_formula_weight         299.33
_chemical_absolute_configuration ad
_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 0.0181 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'
P P 0.2955 0.4335 '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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.1771(4)
_cell_length_b                   5.7977(3)
_cell_length_c                   13.7003(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.684(4)
_cell_angle_gamma                90
_cell_volume                     649.46(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1675
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.632
_cell_measurement_theta_min      3.226
_shelx_estimated_absorpt_T_max   0.871
_shelx_estimated_absorpt_T_min   0.351
_exptl_absorpt_coefficient_mu    4.726
_exptl_absorpt_correction_T_max  0.3207
_exptl_absorpt_correction_T_min  0.1886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0775 before and 0.0450 after correction. The Ratio of minimum to maximum transmission is 0.5881. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2535
_diffrn_reflns_point_group_measured_fraction_full 0.786
_diffrn_reflns_point_group_measured_fraction_max 0.786
_diffrn_reflns_theta_full        66.981
_diffrn_reflns_theta_max         66.981
_diffrn_reflns_theta_min         3.226
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker MicroStar FR-592'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.475
_reflns_Friedel_fraction_full    0.568
_reflns_Friedel_fraction_max     0.568
_reflns_number_gt                1695
_reflns_number_total             1814
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX3 v2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 543 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1814
_refine_ls_number_restraints     71
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.042
_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)+(0.0702P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1034
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C5-C4
 1.5 with sigma of 0.02
 C4-C3
 1.4 with sigma of 0.02
 C3-C2 = C2A-C1A = C2-C1 = C3A-C2A
 1.4 with sigma of 0.02
 S1-C1 = S1A-C1A
 1.75 with sigma of 0.02
 C4-C3A
 1.4 with sigma of 0.02
 S1-C4
 1.75 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3A) = Uanis(S1)
Uanis(C3) = Uanis(S1A)
Uanis(C1A) = Uanis(C2)
Uanis(C1) = Uanis(C2A)
4. Rigid body (RIGU) restrains
 C3, S1A, C2, C1A, C1, C2A, S1, C3A, C4
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(C1A)=Sof(H1AA)=Sof(S1A)=1-FVAR(1)
 Sof(S1)=Sof(C1)=Sof(H1A)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
  C15(H15), C3A(H3A), C2A(H2A), C1A(H1AA)
;
_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 0.5319(4) 0.3628(3) 0.86436(13) 0.0361(5) Uani 0.848(7) 1 d D U P A 1
S2 S 0.63316(15) 0.64226(19) 0.57580(8) 0.0349(3) Uani 1 1 d . . . . .
P1 P 0.79061(16) 0.7455(2) 0.35149(9) 0.0350(3) Uani 1 1 d . . . . .
N1 N 0.9111(5) 0.3345(8) 0.3733(3) 0.0344(9) Uani 1 1 d . . . . .
H1 H 0.935419 0.200034 0.399451 0.041 Uiso 1 1 calc R . . . .
C1 C 0.4086(10) 0.5513(16) 0.9273(6) 0.0354(14) Uani 0.848(7) 1 d D U P A 1
H1A H 0.371529 0.526379 0.991874 0.042 Uiso 0.848(7) 1 calc R . P A 1
C2 C 0.3713(15) 0.7397(18) 0.8727(8) 0.0362(18) Uani 0.848(7) 1 d D U P A 1
H2 H 0.308529 0.865407 0.896214 0.043 Uiso 0.848(7) 1 calc R . P A 1
C3 C 0.434(3) 0.731(3) 0.7780(13) 0.0378(18) Uani 0.848(7) 1 d D U P A 1
H3 H 0.414683 0.845909 0.730052 0.045 Uiso 0.848(7) 1 calc R . P A 1
C4 C 0.5291(6) 0.5347(9) 0.7618(3) 0.0340(10) Uani 1 1 d D U . . .
C5 C 0.6164(6) 0.4612(9) 0.6755(4) 0.0326(10) Uani 1 1 d D . . . .
C6 C 0.6982(6) 0.2598(10) 0.6608(4) 0.0328(10) Uani 1 1 d . . . . .
H6 H 0.702471 0.138392 0.707370 0.039 Uiso 1 1 calc R . . . .
C7 C 0.7759(6) 0.2495(10) 0.5697(4) 0.0353(10) Uani 1 1 d . . . . .
H7 H 0.836820 0.119797 0.548391 0.042 Uiso 1 1 calc R . . . .
C8 C 0.7551(5) 0.4435(9) 0.5153(4) 0.0322(10) Uani 1 1 d . . . . .
C9 C 0.8189(6) 0.4937(9) 0.4194(4) 0.0345(11) Uani 1 1 d . . . . .
C10 C 0.9640(6) 0.3995(9) 0.2820(3) 0.0346(11) Uani 1 1 d . . . . .
C11 C 0.9100(6) 0.6194(9) 0.2557(4) 0.0347(10) Uani 1 1 d . . . . .
C12 C 0.9515(6) 0.7043(9) 0.1624(4) 0.0362(12) Uani 1 1 d . . . . .
H12 H 0.912553 0.850550 0.141217 0.043 Uiso 1 1 calc R . . . .
C13 C 1.0486(7) 0.5737(10) 0.1028(4) 0.0407(12) Uani 1 1 d . . . . .
H13 H 1.079438 0.632736 0.041036 0.049 Uiso 1 1 calc R . . . .
C14 C 1.1025(6) 0.3551(10) 0.1317(4) 0.0374(11) Uani 1 1 d . . . . .
H14 H 1.168457 0.266764 0.088995 0.045 Uiso 1 1 calc R . . . .
C15 C 1.0610(6) 0.2656(10) 0.2219(4) 0.0351(11) Uani 1 1 d . . . . .
H15 H 1.097759 0.117397 0.241982 0.042 Uiso 1 1 calc R . . . .
C3A C 0.529(10) 0.400(9) 0.846(3) 0.0361(5) Uani 0.152(7) 1 d D U P A 2
H3A H 0.579993 0.253320 0.852986 0.043 Uiso 0.152(7) 1 calc R . P A 2
C2A C 0.443(7) 0.516(10) 0.919(4) 0.0354(14) Uani 0.152(7) 1 d D U P A 2
H2A H 0.445157 0.471567 0.986158 0.042 Uiso 0.152(7) 1 calc R . P A 2
C1A C 0.355(10) 0.702(13) 0.883(4) 0.0362(18) Uani 0.152(7) 1 d D U P A 2
H1AA H 0.266502 0.776717 0.913913 0.043 Uiso 0.152(7) 1 calc R . P A 2
S1A S 0.436(5) 0.772(4) 0.7693(17) 0.0378(18) Uani 0.152(7) 1 d D U 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
S1 C1 1.725(6) . ?
S1 C4 1.723(5) . ?
S2 C5 1.730(5) . ?
S2 C8 1.740(5) . ?
P1 C9 1.745(6) . ?
P1 C11 1.800(5) . ?
N1 H1 0.8800 . ?
N1 C9 1.353(7) . ?
N1 C10 1.380(6) . ?
C1 H1A 0.9500 . ?
C1 C2 1.357(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.402(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(13) . ?
C4 C5 1.451(6) . ?
C4 C3A 1.40(2) . ?
C4 S1A 1.577(19) . ?
C5 C6 1.362(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.409(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.359(8) . ?
C8 C9 1.449(7) . ?
C10 C11 1.395(8) . ?
C10 C15 1.387(7) . ?
C11 C12 1.415(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.374(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.397(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(7) . ?
C15 H15 0.9500 . ?
C3A H3A 0.9500 . ?
C3A C2A 1.40(3) . ?
C2A H2A 0.9500 . ?
C2A C1A 1.39(3) . ?
C1A H1AA 0.9500 . ?
C1A S1A 1.75(2) . ?

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
C4 S1 C1 92.2(3) . . ?
C5 S2 C8 91.5(2) . . ?
C9 P1 C11 88.8(2) . . ?
C9 N1 H1 122.6 . . ?
C9 N1 C10 114.8(4) . . ?
C10 N1 H1 122.6 . . ?
S1 C1 H1A 124.3 . . ?
C2 C1 S1 111.3(6) . . ?
C2 C1 H1A 124.3 . . ?
C1 C2 H2 123.3 . . ?
C1 C2 C3 113.4(9) . . ?
C3 C2 H2 123.3 . . ?
C2 C3 H3 123.5 . . ?
C4 C3 C2 112.9(10) . . ?
C4 C3 H3 123.5 . . ?
C3 C4 S1 110.0(6) . . ?
C3 C4 C5 130.5(6) . . ?
C5 C4 S1 119.5(4) . . ?
C5 C4 S1A 123.4(7) . . ?
C3A C4 C5 121(2) . . ?
C3A C4 S1A 116(2) . . ?
C4 C5 S2 120.6(4) . . ?
C6 C5 S2 111.1(3) . . ?
C6 C5 C4 128.3(4) . . ?
C5 C6 H6 123.4 . . ?
C5 C6 C7 113.2(5) . . ?
C7 C6 H6 123.4 . . ?
C6 C7 H7 123.3 . . ?
C8 C7 C6 113.3(5) . . ?
C8 C7 H7 123.3 . . ?
C7 C8 S2 110.8(3) . . ?
C7 C8 C9 128.3(5) . . ?
C9 C8 S2 120.9(4) . . ?
N1 C9 P1 113.1(4) . . ?
N1 C9 C8 119.7(5) . . ?
C8 C9 P1 127.2(4) . . ?
N1 C10 C11 112.4(4) . . ?
N1 C10 C15 124.9(5) . . ?
C15 C10 C11 122.6(5) . . ?
C10 C11 P1 110.8(4) . . ?
C10 C11 C12 118.2(4) . . ?
C12 C11 P1 130.9(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.5(5) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 121.1 . . ?
C14 C15 C10 117.9(5) . . ?
C14 C15 H15 121.1 . . ?
C4 C3A H3A 125.4 . . ?
C4 C3A C2A 109(4) . . ?
C2A C3A H3A 125.4 . . ?
C3A C2A H2A 123.9 . . ?
C1A C2A C3A 112(5) . . ?
C1A C2A H2A 123.9 . . ?
C2A C1A H1AA 126.2 . . ?
C2A C1A S1A 108(4) . . ?
S1A C1A H1AA 126.2 . . ?
C4 S1A C1A 92(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
