# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_ff1
_database_code_depnum_ccdc_archive 'CCDC 2301193'
loop_
_audit_author_name
_audit_author_address
'Zeqi Jiang'
;NBC institution
China
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2024-03-27 downloaded from the CCDC.
;
_audit_creation_date             2023-10-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 N O3 P S'
_chemical_formula_sum            'C19 H18 N O3 P S'
_chemical_formula_weight         371.37
_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'
O O 0.0492 0.0322 '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           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                   17.3863(7)
_cell_length_b                   8.7024(3)
_cell_length_c                   12.2510(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.256(2)
_cell_angle_gamma                90
_cell_volume                     1811.36(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7082
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.78
_cell_measurement_theta_min      5.21
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.574
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6160
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1356 before and 0.0770 after correction.
The Ratio of minimum to maximum transmission is 0.8177.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19403
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.122
_diffrn_reflns_theta_min         5.207
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2988
_reflns_number_total             3426
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.060
_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)+(0.0529P)²+0.5038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1023
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00G(H00G), C00I(H00I), C00J(H00J), C00L(H00N),
 C00M(H00O), C00N(H00P), C00O(H00Q), C00P(H00R)
2.c Idealised Me refined as rotating group:
 C00H(H00C,H00F,H00H), C00K(H00K,H00L,H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S001 S 0.37446(2) 0.68333(5) 0.37970(3) 0.02612(14) Uani 1 1 d . . . . .
P002 P 0.21353(2) 0.52782(5) 0.31694(4) 0.02371(14) Uani 1 1 d . . . . .
O003 O 0.52930(7) 0.81334(15) 0.46545(10) 0.0295(3) Uani 1 1 d . . . . .
O004 O 0.21623(8) 0.59402(16) 0.20639(11) 0.0339(3) Uani 1 1 d . . . . .
O005 O 0.55574(8) 0.69694(17) 0.63321(11) 0.0366(3) Uani 1 1 d . . . . .
N006 N 0.32288(8) 0.50881(18) 0.51725(12) 0.0264(3) Uani 1 1 d . . . . .
C007 C 0.20542(10) 0.3219(2) 0.31747(15) 0.0266(4) Uani 1 1 d . . . . .
C008 C 0.30421(10) 0.5675(2) 0.41622(14) 0.0242(4) Uani 1 1 d . . . . .
C009 C 0.39645(10) 0.5562(2) 0.57186(14) 0.0253(4) Uani 1 1 d . . . . .
C00A C 0.43339(10) 0.6518(2) 0.50918(14) 0.0250(4) Uani 1 1 d . . . . .
C00B C 0.51221(10) 0.7208(2) 0.54428(14) 0.0258(4) Uani 1 1 d . . . . .
C00C C 0.13518(10) 0.6003(2) 0.37762(15) 0.0266(4) Uani 1 1 d . . . . .
C00D C 0.18244(11) 0.2439(2) 0.40459(16) 0.0310(4) Uani 1 1 d . . . . .
H00D H 0.168486 0.299903 0.464074 0.037 Uiso 1 1 calc R U . . .
C00E C 0.14660(11) 0.6814(2) 0.47763(16) 0.0322(4) Uani 1 1 d . . . . .
H00E H 0.198368 0.697031 0.520341 0.039 Uiso 1 1 calc R U . . .
C00F C 0.60739(10) 0.8850(2) 0.49363(16) 0.0325(4) Uani 1 1 d . . . . .
H00A H 0.648655 0.805169 0.512419 0.039 Uiso 1 1 calc R U . . .
H00B H 0.611086 0.953807 0.558888 0.039 Uiso 1 1 calc R U . . .
C00G C 0.22608(11) 0.2391(2) 0.23100(16) 0.0318(4) Uani 1 1 d . . . . .
H00G H 0.242670 0.291526 0.171996 0.038 Uiso 1 1 calc R U . . .
C00H C 0.42791(12) 0.5002(2) 0.68774(15) 0.0343(4) Uani 1 1 d . . . . .
H00C H 0.385571 0.450709 0.716411 0.051 Uiso 1 1 calc R U . . .
H00F H 0.448693 0.587202 0.735811 0.051 Uiso 1 1 calc R U . . .
H00H H 0.470145 0.425814 0.687171 0.051 Uiso 1 1 calc R U . . .
C00I C 0.05884(11) 0.5792(3) 0.31565(18) 0.0422(5) Uani 1 1 d . . . . .
H00I H 0.050293 0.522872 0.247704 0.051 Uiso 1 1 calc R U . . .
C00J C 0.08271(13) 0.7394(3) 0.51502(19) 0.0437(5) Uani 1 1 d . . . . .
H00J H 0.090555 0.793382 0.583913 0.052 Uiso 1 1 calc R U . . .
C00K C 0.61832(11) 0.9748(2) 0.39398(16) 0.0344(4) Uani 1 1 d . . . . .
H00K H 0.614675 0.905570 0.330014 0.052 Uiso 1 1 calc R U . . .
H00L H 0.670164 1.024195 0.410303 0.052 Uiso 1 1 calc R U . . .
H00M H 0.577287 1.053629 0.376319 0.052 Uiso 1 1 calc R U . . .
C00L C 0.19959(12) 0.0040(2) 0.3175(2) 0.0409(5) Uani 1 1 d . . . . .
H00N H 0.197338 -0.105107 0.317233 0.049 Uiso 1 1 calc R U . . .
C00M C 0.22248(12) 0.0802(2) 0.23087(19) 0.0400(5) Uani 1 1 d . . . . .
H00O H 0.235770 0.023597 0.171164 0.048 Uiso 1 1 calc R U . . .
C00N C 0.17989(12) 0.0853(2) 0.40462(19) 0.0389(5) Uani 1 1 d . . . . .
H00P H 0.164652 0.032173 0.464385 0.047 Uiso 1 1 calc R U . . .
C00O C -0.00446(13) 0.6399(3) 0.3529(2) 0.0564(7) Uani 1 1 d . . . . .
H00Q H -0.056341 0.627104 0.309812 0.068 Uiso 1 1 calc R U . . .
C00P C 0.00773(13) 0.7188(3) 0.4523(2) 0.0533(6) Uani 1 1 d . . . . .
H00R H -0.035962 0.759558 0.477942 0.064 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
S001 C008 1.7145(17) . ?
S001 C00A 1.7180(17) . ?
P002 O004 1.4815(13) . ?
P002 C007 1.7976(19) . ?
P002 C008 1.8084(17) . ?
P002 C00C 1.7992(18) . ?
O003 C00B 1.339(2) . ?
O003 C00F 1.467(2) . ?
O005 C00B 1.205(2) . ?
N006 C008 1.314(2) . ?
N006 C009 1.375(2) . ?
C007 C00D 1.393(3) . ?
C007 C00G 1.390(3) . ?
C009 C00A 1.380(3) . ?
C009 C00H 1.491(2) . ?
C00A C00B 1.474(2) . ?
C00C C00E 1.391(3) . ?
C00C C00I 1.394(3) . ?
C00D H00D 0.9500 . ?
C00D C00N 1.381(3) . ?
C00E H00E 0.9500 . ?
C00E C00J 1.384(3) . ?
C00F H00A 0.9900 . ?
C00F H00B 0.9900 . ?
C00F C00K 1.495(3) . ?
C00G H00G 0.9500 . ?
C00G C00M 1.384(3) . ?
C00H H00C 0.9800 . ?
C00H H00F 0.9800 . ?
C00H H00H 0.9800 . ?
C00I H00I 0.9500 . ?
C00I C00O 1.383(3) . ?
C00J H00J 0.9500 . ?
C00J C00P 1.377(3) . ?
C00K H00K 0.9800 . ?
C00K H00L 0.9800 . ?
C00K H00M 0.9800 . ?
C00L H00N 0.9500 . ?
C00L C00M 1.379(3) . ?
C00L C00N 1.384(3) . ?
C00M H00O 0.9500 . ?
C00N H00P 0.9500 . ?
C00O H00Q 0.9500 . ?
C00O C00P 1.375(3) . ?
C00P H00R 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
C008 S001 C00A 89.05(8) . . ?
O004 P002 C007 114.12(8) . . ?
O004 P002 C008 110.39(8) . . ?
O004 P002 C00C 114.52(8) . . ?
C007 P002 C008 104.24(8) . . ?
C007 P002 C00C 106.34(8) . . ?
C00C P002 C008 106.47(8) . . ?
C00B O003 C00F 114.97(14) . . ?
C008 N006 C009 111.09(15) . . ?
C00D C007 P002 121.61(14) . . ?
C00G C007 P002 118.75(14) . . ?
C00G C007 C00D 119.58(18) . . ?
S001 C008 P002 120.29(10) . . ?
N006 C008 S001 115.28(13) . . ?
N006 C008 P002 124.39(13) . . ?
N006 C009 C00A 113.89(15) . . ?
N006 C009 C00H 118.72(16) . . ?
C00A C009 C00H 127.38(16) . . ?
C009 C00A S001 110.69(13) . . ?
C009 C00A C00B 126.65(16) . . ?
C00B C00A S001 122.66(13) . . ?
O003 C00B C00A 111.69(15) . . ?
O005 C00B O003 124.24(16) . . ?
O005 C00B C00A 124.06(17) . . ?
C00E C00C P002 124.25(14) . . ?
C00E C00C C00I 119.21(17) . . ?
C00I C00C P002 116.45(15) . . ?
C007 C00D H00D 119.9 . . ?
C00N C00D C007 120.12(18) . . ?
C00N C00D H00D 119.9 . . ?
C00C C00E H00E 119.9 . . ?
C00J C00E C00C 120.14(18) . . ?
C00J C00E H00E 119.9 . . ?
O003 C00F H00A 110.2 . . ?
O003 C00F H00B 110.2 . . ?
O003 C00F C00K 107.56(15) . . ?
H00A C00F H00B 108.5 . . ?
C00K C00F H00A 110.2 . . ?
C00K C00F H00B 110.2 . . ?
C007 C00G H00G 120.0 . . ?
C00M C00G C007 119.99(18) . . ?
C00M C00G H00G 120.0 . . ?
C009 C00H H00C 109.5 . . ?
C009 C00H H00F 109.5 . . ?
C009 C00H H00H 109.5 . . ?
H00C C00H H00F 109.5 . . ?
H00C C00H H00H 109.5 . . ?
H00F C00H H00H 109.5 . . ?
C00C C00I H00I 119.9 . . ?
C00O C00I C00C 120.1(2) . . ?
C00O C00I H00I 119.9 . . ?
C00E C00J H00J 120.0 . . ?
C00P C00J C00E 119.9(2) . . ?
C00P C00J H00J 120.0 . . ?
C00F C00K H00K 109.5 . . ?
C00F C00K H00L 109.5 . . ?
C00F C00K H00M 109.5 . . ?
H00K C00K H00L 109.5 . . ?
H00K C00K H00M 109.5 . . ?
H00L C00K H00M 109.5 . . ?
C00M C00L H00N 119.8 . . ?
C00M C00L C00N 120.45(19) . . ?
C00N C00L H00N 119.8 . . ?
C00G C00M H00O 120.0 . . ?
C00L C00M C00G 119.98(19) . . ?
C00L C00M H00O 120.0 . . ?
C00D C00N C00L 119.87(19) . . ?
C00D C00N H00P 120.1 . . ?
C00L C00N H00P 120.1 . . ?
C00I C00O H00Q 120.0 . . ?
C00P C00O C00I 120.0(2) . . ?
C00P C00O H00Q 120.0 . . ?
C00J C00P H00R 119.7 . . ?
C00O C00P C00J 120.6(2) . . ?
C00O C00P H00R 119.7 . . ?

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
S001 C00A C00B O003 2.5(2) . . . . ?
S001 C00A C00B O005 -177.64(15) . . . . ?
P002 C007 C00D C00N -177.36(15) . . . . ?
P002 C007 C00G C00M 178.23(14) . . . . ?
P002 C00C C00E C00J 176.77(17) . . . . ?
P002 C00C C00I C00O -175.9(2) . . . . ?
O004 P002 C007 C00D -163.55(14) . . . . ?
O004 P002 C007 C00G 19.37(17) . . . . ?
O004 P002 C008 S001 5.77(14) . . . . ?
O004 P002 C008 N006 -171.84(15) . . . . ?
O004 P002 C00C C00E -117.56(16) . . . . ?
O004 P002 C00C C00I 58.97(18) . . . . ?
N006 C009 C00A S001 0.3(2) . . . . ?
N006 C009 C00A C00B -179.84(16) . . . . ?
C007 P002 C008 S001 128.73(11) . . . . ?
C007 P002 C008 N006 -48.88(17) . . . . ?
C007 P002 C00C C00E 115.44(16) . . . . ?
C007 P002 C00C C00I -68.02(17) . . . . ?
C007 C00D C00N C00L -0.5(3) . . . . ?
C007 C00G C00M C00L -1.0(3) . . . . ?
C008 S001 C00A C009 -0.09(14) . . . . ?
C008 S001 C00A C00B -179.93(15) . . . . ?
C008 P002 C007 C00D 75.96(16) . . . . ?
C008 P002 C007 C00G -101.12(15) . . . . ?
C008 P002 C00C C00E 4.72(18) . . . . ?
C008 P002 C00C C00I -178.75(16) . . . . ?
C008 N006 C009 C00A -0.5(2) . . . . ?
C008 N006 C009 C00H -179.63(16) . . . . ?
C009 N006 C008 S001 0.4(2) . . . . ?
C009 N006 C008 P002 178.10(13) . . . . ?
C009 C00A C00B O003 -177.27(17) . . . . ?
C009 C00A C00B O005 2.5(3) . . . . ?
C00A S001 C008 P002 -177.99(12) . . . . ?
C00A S001 C008 N006 -0.17(15) . . . . ?
C00B O003 C00F C00K 176.23(15) . . . . ?
C00C P002 C007 C00D -36.32(17) . . . . ?
C00C P002 C007 C00G 146.59(14) . . . . ?
C00C P002 C008 S001 -119.08(11) . . . . ?
C00C P002 C008 N006 63.31(17) . . . . ?
C00C C00E C00J C00P -1.0(3) . . . . ?
C00C C00I C00O C00P -1.3(4) . . . . ?
C00D C007 C00G C00M 1.1(3) . . . . ?
C00E C00C C00I C00O 0.8(3) . . . . ?
C00E C00J C00P C00O 0.5(4) . . . . ?
C00F O003 C00B O005 0.9(3) . . . . ?
C00F O003 C00B C00A -179.24(15) . . . . ?
C00G C007 C00D C00N -0.3(3) . . . . ?
C00H C009 C00A S001 179.42(16) . . . . ?
C00H C009 C00A C00B -0.7(3) . . . . ?
C00I C00C C00E C00J 0.3(3) . . . . ?
C00I C00O C00P C00J 0.6(4) . . . . ?
C00M C00L C00N C00D 0.6(3) . . . . ?
C00N C00L C00M C00G 0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
