# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2305323'
loop_
_audit_author_name
_audit_author_address
'Guangping Sun'
;Nantong University
China
;
_audit_update_record             
;
2023-11-02 deposited with the CCDC.	2023-12-29 downloaded from the CCDC.
;
_audit_creation_date             2023-03-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 N O P S'
_chemical_formula_sum            'C19 H14 N O P S'
_chemical_formula_weight         335.34
_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'
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.385(2)
_cell_length_b                   10.473(3)
_cell_length_c                   10.511(3)
_cell_angle_alpha                109.339(3)
_cell_angle_beta                 92.044(3)
_cell_angle_gamma                102.717(3)
_cell_volume                     843.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.497
_cell_measurement_theta_min      2.396
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0399 before and 0.0309 after correction.
The Ratio of minimum to maximum transmission is 0.9383.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24318
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.862
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3532
_reflns_number_total             3858
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3858
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.098
_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)+(0.0465P)²+0.2808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0970
_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:
 C008(H008), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N)
;
_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
P001 P 0.38710(4) 0.79370(3) 0.73429(3) 0.02965(10) Uani 1 1 d . . . . .
S002 S 0.25312(5) 0.64809(4) 0.92659(4) 0.04868(12) Uani 1 1 d . . . . .
O003 O 0.32463(13) 0.90357(10) 0.83391(10) 0.0411(2) Uani 1 1 d . . . . .
N004 N 0.39852(18) 0.52693(13) 0.72353(14) 0.0461(3) Uani 1 1 d . . . . .
C005 C 0.60561(16) 0.84102(13) 0.73203(14) 0.0333(3) Uani 1 1 d . . . . .
C006 C 0.29068(16) 0.74361(15) 0.56353(14) 0.0354(3) Uani 1 1 d . . . . .
C007 C 0.34935(16) 0.63914(14) 0.78128(13) 0.0337(3) Uani 1 1 d . . . . .
C008 C 0.69648(19) 0.95326(16) 0.84146(15) 0.0416(3) Uani 1 1 d . . . . .
H008 H 0.6435 1.0031 0.9101 0.050 Uiso 1 1 calc R U . . .
C009 C 0.3601(2) 0.43648(15) 0.79536(17) 0.0459(4) Uani 1 1 d . . . . .
C00A C 0.2810(2) 0.48482(17) 0.90918(17) 0.0470(4) Uani 1 1 d . . . . .
C00B C 0.6838(2) 0.76687(18) 0.6290(2) 0.0547(4) Uani 1 1 d . . . . .
H00B H 0.6232 0.6922 0.5554 0.066 Uiso 1 1 calc R U . . .
C00C C 0.8663(2) 0.9903(2) 0.8476(2) 0.0564(4) Uani 1 1 d . . . . .
H00C H 0.9277 1.0654 0.9205 0.068 Uiso 1 1 calc R U . . .
C00D C 0.2107(3) 0.6094(2) 0.48380(18) 0.0608(5) Uani 1 1 d . . . . .
H00D H 0.2116 0.5357 0.5143 0.073 Uiso 1 1 calc R U . . .
C00E C 0.2891(3) 0.8512(2) 0.51527(19) 0.0596(5) Uani 1 1 d . . . . .
H00E H 0.3428 0.9423 0.5683 0.072 Uiso 1 1 calc R U . . .
C00F C 0.9442(2) 0.9169(2) 0.7468(3) 0.0688(6) Uani 1 1 d . . . . .
H00F H 1.0584 0.9420 0.7519 0.083 Uiso 1 1 calc R U . . .
C00G C 0.3985(3) 0.3066(2) 0.7625(3) 0.0739(6) Uani 1 1 d . . . . .
H00G H 0.4523 0.2732 0.6871 0.089 Uiso 1 1 calc R U . . .
C00H C 0.3543(4) 0.2298(2) 0.8451(3) 0.0865(9) Uani 1 1 d . . . . .
H00H H 0.3781 0.1431 0.8245 0.104 Uiso 1 1 calc R U . . .
C00I C 0.8546(2) 0.8063(2) 0.6380(3) 0.0742(6) Uani 1 1 d . . . . .
H00I H 0.9088 0.7573 0.5698 0.089 Uiso 1 1 calc R U . . .
C00J C 0.2376(3) 0.4046(2) 0.9919(2) 0.0739(6) Uani 1 1 d . . . . .
H00J H 0.1844 0.4364 1.0679 0.089 Uiso 1 1 calc R U . . .
C00K C 0.1283(3) 0.5844(3) 0.3574(2) 0.0838(8) Uani 1 1 d . . . . .
H00K H 0.0730 0.4938 0.3042 0.101 Uiso 1 1 calc R U . . .
C00L C 0.2760(3) 0.2782(3) 0.9573(3) 0.0865(9) Uani 1 1 d . . . . .
H00L H 0.2484 0.2236 1.0110 0.104 Uiso 1 1 calc R U . . .
C00M C 0.2081(3) 0.8243(3) 0.3888(2) 0.0788(7) Uani 1 1 d . . . . .
H00M H 0.2083 0.8971 0.3566 0.095 Uiso 1 1 calc R U . . .
C00N C 0.1276(3) 0.6904(3) 0.3109(2) 0.0787(7) Uani 1 1 d . . . . .
H00N H 0.0725 0.6722 0.2260 0.094 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
P001 O003 1.4837(10) . ?
P001 C005 1.7927(15) . ?
P001 C006 1.7991(14) . ?
P001 C007 1.8108(14) . ?
S002 C007 1.7375(14) . ?
S002 C00A 1.7274(18) . ?
N004 C007 1.2954(18) . ?
N004 C009 1.3884(19) . ?
C005 C008 1.390(2) . ?
C005 C00B 1.387(2) . ?
C006 C00D 1.376(2) . ?
C006 C00E 1.383(2) . ?
C008 H008 0.9300 . ?
C008 C00C 1.384(2) . ?
C009 C00A 1.389(3) . ?
C009 C00G 1.401(2) . ?
C00A C00J 1.402(2) . ?
C00B H00B 0.9300 . ?
C00B C00I 1.391(3) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.367(3) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.391(3) . ?
C00E H00E 0.9300 . ?
C00E C00M 1.382(3) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.376(3) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.375(3) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.373(4) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00L 1.365(4) . ?
C00K H00K 0.9300 . ?
C00K C00N 1.354(4) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.370(4) . ?
C00N H00N 0.9300 . ?

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
O003 P001 C005 113.32(6) . . ?
O003 P001 C006 113.23(6) . . ?
O003 P001 C007 109.39(7) . . ?
C005 P001 C006 107.90(6) . . ?
C005 P001 C007 104.87(6) . . ?
C006 P001 C007 107.66(6) . . ?
C00A S002 C007 88.39(7) . . ?
C007 N004 C009 109.83(13) . . ?
C008 C005 P001 117.21(11) . . ?
C00B C005 P001 122.26(11) . . ?
C00B C005 C008 120.48(14) . . ?
C00D C006 P001 124.67(12) . . ?
C00D C006 C00E 119.04(15) . . ?
C00E C006 P001 116.13(12) . . ?
S002 C007 P001 116.66(8) . . ?
N004 C007 P001 126.33(11) . . ?
N004 C007 S002 116.77(10) . . ?
C005 C008 H008 120.2 . . ?
C00C C008 C005 119.54(16) . . ?
C00C C008 H008 120.2 . . ?
N004 C009 C00A 115.00(14) . . ?
N004 C009 C00G 124.93(18) . . ?
C00A C009 C00G 120.05(17) . . ?
C009 C00A S002 110.01(11) . . ?
C009 C00A C00J 120.77(19) . . ?
C00J C00A S002 129.21(17) . . ?
C005 C00B H00B 120.6 . . ?
C005 C00B C00I 118.75(17) . . ?
C00I C00B H00B 120.6 . . ?
C008 C00C H00C 119.9 . . ?
C00F C00C C008 120.23(17) . . ?
C00F C00C H00C 119.9 . . ?
C006 C00D H00D 120.1 . . ?
C006 C00D C00K 119.72(19) . . ?
C00K C00D H00D 120.1 . . ?
C006 C00E H00E 119.8 . . ?
C00M C00E C006 120.47(19) . . ?
C00M C00E H00E 119.8 . . ?
C00C C00F H00F 119.8 . . ?
C00C C00F C00I 120.41(17) . . ?
C00I C00F H00F 119.8 . . ?
C009 C00G H00G 121.0 . . ?
C00H C00G C009 118.0(2) . . ?
C00H C00G H00G 121.0 . . ?
C00G C00H H00H 119.2 . . ?
C00L C00H C00G 121.6(2) . . ?
C00L C00H H00H 119.2 . . ?
C00B C00I H00I 119.7 . . ?
C00F C00I C00B 120.60(19) . . ?
C00F C00I H00I 119.7 . . ?
C00A C00J H00J 121.0 . . ?
C00L C00J C00A 118.0(2) . . ?
C00L C00J H00J 121.0 . . ?
C00D C00K H00K 119.6 . . ?
C00N C00K C00D 120.8(2) . . ?
C00N C00K H00K 119.6 . . ?
C00H C00L H00L 119.2 . . ?
C00J C00L C00H 121.59(19) . . ?
C00J C00L H00L 119.2 . . ?
C00E C00M H00M 120.0 . . ?
C00N C00M C00E 119.9(2) . . ?
C00N C00M H00M 120.0 . . ?
C00K C00N C00M 120.01(18) . . ?
C00K C00N H00N 120.0 . . ?
C00M C00N H00N 120.0 . . ?

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
P001 C005 C008 C00C 177.23(12) . . . . ?
P001 C005 C00B C00I -176.99(16) . . . . ?
P001 C006 C00D C00K 174.48(18) . . . . ?
P001 C006 C00E C00M -175.59(18) . . . . ?
S002 C00A C00J C00L -178.88(15) . . . . ?
O003 P001 C005 C008 15.80(13) . . . . ?
O003 P001 C005 C00B -166.63(13) . . . . ?
O003 P001 C006 C00D -123.95(16) . . . . ?
O003 P001 C006 C00E 51.40(15) . . . . ?
O003 P001 C007 S002 -0.25(10) . . . . ?
O003 P001 C007 N004 -174.39(13) . . . . ?
N004 C009 C00A S002 0.24(18) . . . . ?
N004 C009 C00A C00J -179.02(16) . . . . ?
N004 C009 C00G C00H 178.98(19) . . . . ?
C005 P001 C006 C00D 109.80(16) . . . . ?
C005 P001 C006 C00E -74.85(14) . . . . ?
C005 P001 C007 S002 121.60(8) . . . . ?
C005 P001 C007 N004 -52.55(14) . . . . ?
C005 C008 C00C C00F -0.1(3) . . . . ?
C005 C00B C00I C00F -0.2(3) . . . . ?
C006 P001 C005 C008 142.00(11) . . . . ?
C006 P001 C005 C00B -40.43(15) . . . . ?
C006 P001 C007 S002 -123.67(8) . . . . ?
C006 P001 C007 N004 62.18(15) . . . . ?
C006 C00D C00K C00N 0.9(4) . . . . ?
C006 C00E C00M C00N 0.5(4) . . . . ?
C007 P001 C005 C008 -103.44(11) . . . . ?
C007 P001 C005 C00B 74.13(15) . . . . ?
C007 P001 C006 C00D -2.90(17) . . . . ?
C007 P001 C006 C00E 172.45(13) . . . . ?
C007 S002 C00A C009 -0.14(12) . . . . ?
C007 S002 C00A C00J 179.04(18) . . . . ?
C007 N004 C009 C00A -0.2(2) . . . . ?
C007 N004 C009 C00G -178.72(17) . . . . ?
C008 C005 C00B C00I 0.5(3) . . . . ?
C008 C00C C00F C00I 0.4(3) . . . . ?
C009 N004 C007 P001 174.25(11) . . . . ?
C009 N004 C007 S002 0.11(17) . . . . ?
C009 C00A C00J C00L 0.2(3) . . . . ?
C009 C00G C00H C00L -0.5(4) . . . . ?
C00A S002 C007 P001 -174.70(9) . . . . ?
C00A S002 C007 N004 0.02(13) . . . . ?
C00A C009 C00G C00H 0.6(3) . . . . ?
C00A C00J C00L C00H -0.1(3) . . . . ?
C00B C005 C008 C00C -0.4(2) . . . . ?
C00C C00F C00I C00B -0.3(4) . . . . ?
C00D C006 C00E C00M 0.0(3) . . . . ?
C00D C00K C00N C00M -0.3(4) . . . . ?
C00E C006 C00D C00K -0.7(3) . . . . ?
C00E C00M C00N C00K -0.4(4) . . . . ?
C00G C009 C00A S002 178.81(15) . . . . ?
C00G C009 C00A C00J -0.5(3) . . . . ?
C00G C00H C00L C00J 0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
