# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_11095
_database_code_depnum_ccdc_archive 'CCDC 2193492'
loop_
_audit_author_name
_audit_author_address
'Rongqiang Tian'
;Zhengzhou University
China
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-10-12 downloaded from the CCDC.
;
_audit_creation_date             2022-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H22 N O P S'
_chemical_formula_sum            'C20 H23 N O P S'
_chemical_formula_weight         356.42
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     ' '
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.43300(10)
_cell_length_b                   11.85120(10)
_cell_length_c                   14.09910(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.0950(10)
_cell_angle_gamma                90
_cell_volume                     1909.08(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5533
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      73.3620
_cell_measurement_theta_min      3.1640
_shelx_estimated_absorpt_T_max   0.652
_shelx_estimated_absorpt_T_min   0.652
_exptl_absorpt_coefficient_mu    2.334
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9165
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.563
_diffrn_reflns_theta_min         4.876
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00   0.00   0.50    0.50    --    0.00 -57.00-150.00   66
  2  ω    -84.00 -36.00   0.50    0.50    --    0.00 -57.00-150.00   96
  3  ω    -89.00 -44.00   0.50    0.50    --    0.00 -38.00  90.00   90
  4  ω    -30.00  28.00   0.50    0.50    --    0.00 -38.00  90.00  116
  5  ω      9.00 128.00   0.50    0.50    --   98.80 -61.00-180.00  238
  6  ω     81.00 186.00   0.50    0.50    --   98.80  45.00  90.00  210
  7  ω    145.00 170.00   0.50    0.50    --   98.80   0.00  90.00   50
  8  ω     40.00  77.00   0.50    0.50    --   98.80 -45.00  30.00   74
  9  ω     24.00 127.00   0.50    0.50    --   98.80   0.00  90.00  206
 10  ω     83.00 120.00   0.50    0.50    --   98.80 -45.00  30.00   74
 11  ω     77.00 103.00   0.50    0.50    --   98.80 -82.00 150.00   52
 12  ω     28.00 126.00   0.50    0.50    --   98.80 -82.00 179.79  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1335571000
_diffrn_orient_matrix_UB_12      -0.0167943000
_diffrn_orient_matrix_UB_13      0.0007245000
_diffrn_orient_matrix_UB_21      0.0075336000
_diffrn_orient_matrix_UB_22      -0.0130417000
_diffrn_orient_matrix_UB_23      0.1087579000
_diffrn_orient_matrix_UB_31      -0.0167591000
_diffrn_orient_matrix_UB_32      0.1282653000
_diffrn_orient_matrix_UB_33      0.0112083000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3432
_reflns_number_total             3760
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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         0.234
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.066
_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)+(0.0523P)²+0.3990P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0945
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C14(H14A,H14B,H14C)
;
_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 0.41046(4) 0.12690(3) 0.33992(3) 0.04981(14) Uani 1 1 d . . . . .
P1 P 0.36671(3) 0.27935(3) 0.30094(2) 0.02878(11) Uani 1 1 d . . . . .
O1 O 0.42083(9) 0.31089(10) 0.05263(7) 0.0395(3) Uani 1 1 d . . . . .
N1 N 0.54764(10) 0.30743(11) 0.07122(8) 0.0343(3) Uani 1 1 d . . . . .
C1 C 0.28476(13) 0.47312(12) 0.38932(10) 0.0354(3) Uani 1 1 d . . . . .
H1 H 0.2510 0.4918 0.3304 0.042 Uiso 1 1 calc R . . . .
C2 C 0.26989(15) 0.54339(14) 0.46703(12) 0.0448(4) Uani 1 1 d . . . . .
H2 H 0.2257 0.6089 0.4601 0.054 Uiso 1 1 calc R . . . .
C3 C 0.32064(16) 0.51599(16) 0.55430(12) 0.0503(4) Uani 1 1 d . . . . .
H3 H 0.3105 0.5631 0.6061 0.060 Uiso 1 1 calc R . . . .
C4 C 0.38631(15) 0.41913(18) 0.56497(11) 0.0509(4) Uani 1 1 d . . . . .
H4 H 0.4209 0.4014 0.6238 0.061 Uiso 1 1 calc R . . . .
C5 C 0.40101(13) 0.34806(15) 0.48834(11) 0.0403(3) Uani 1 1 d . . . . .
H5 H 0.4449 0.2824 0.4960 0.048 Uiso 1 1 calc R . . . .
C6 C 0.35035(11) 0.37466(11) 0.40012(9) 0.0294(3) Uani 1 1 d . . . . .
C7 C 0.23775(12) 0.29156(13) 0.22667(11) 0.0375(3) Uani 1 1 d . . . . .
H7 H 0.1648 0.2659 0.2444 0.045 Uiso 1 1 calc R . . . .
C8 C 0.25543(12) 0.34059(12) 0.14383(10) 0.0346(3) Uani 1 1 d . . . . .
C9 C 0.16463(15) 0.35475(16) 0.06489(13) 0.0504(4) Uani 1 1 d . . . . .
H9A H 0.1544 0.4336 0.0512 0.076 Uiso 1 1 calc GR . . . .
H9B H 0.0917 0.3233 0.0839 0.076 Uiso 1 1 calc GR . . . .
H9C H 0.1898 0.3164 0.0092 0.076 Uiso 1 1 calc GR . . . .
C10 C 0.38816(14) 0.50504(14) 0.10278(11) 0.0411(3) Uani 1 1 d . . . . .
H10A H 0.4681 0.5236 0.0912 0.062 Uiso 1 1 calc GR . . . .
H10B H 0.3614 0.5500 0.1543 0.062 Uiso 1 1 calc GR . . . .
H10C H 0.3405 0.5201 0.0467 0.062 Uiso 1 1 calc GR . . . .
C11 C 0.37935(12) 0.38103(12) 0.12815(9) 0.0301(3) Uani 1 1 d . . . . .
C12 C 0.46031(11) 0.34965(11) 0.21521(9) 0.0249(3) Uani 1 1 d . . . . .
H12 H 0.4951 0.4180 0.2434 0.030 Uiso 1 1 calc R . . . .
C13 C 0.55608(11) 0.27569(11) 0.17294(9) 0.0276(3) Uani 1 1 d . . . . .
H13 H 0.5368 0.1957 0.1804 0.033 Uiso 1 1 calc R . . . .
C14 C 0.58908(15) 0.21808(17) 0.01047(11) 0.0508(5) Uani 1 1 d . . . . .
H14A H 0.5448 0.1506 0.0207 0.076 Uiso 1 1 calc GR . . . .
H14B H 0.6704 0.2039 0.0253 0.076 Uiso 1 1 calc GR . . . .
H14C H 0.5795 0.2406 -0.0547 0.076 Uiso 1 1 calc GR . . . .
C15 C 0.67885(11) 0.29846(11) 0.21196(9) 0.0275(3) Uani 1 1 d . . . . .
C16 C 0.74338(14) 0.38875(15) 0.18060(12) 0.0436(4) Uani 1 1 d . . . . .
H16 H 0.7110 0.4368 0.1346 0.052 Uiso 1 1 calc R . . . .
C17 C 0.85596(14) 0.40856(16) 0.21691(14) 0.0522(4) Uani 1 1 d . . . . .
H17 H 0.8991 0.4685 0.1940 0.063 Uiso 1 1 calc R . . . .
C18 C 0.90389(14) 0.34003(17) 0.28651(12) 0.0482(4) Uani 1 1 d . . . . .
H18 H 0.9788 0.3543 0.3116 0.058 Uiso 1 1 calc R . . . .
C19 C 0.84062(15) 0.25020(17) 0.31893(12) 0.0501(4) Uani 1 1 d . . . . .
H19 H 0.8728 0.2035 0.3661 0.060 Uiso 1 1 calc R . . . .
C20 C 0.72876(14) 0.22902(14) 0.28141(11) 0.0399(3) Uani 1 1 d . . . . .
H20 H 0.6869 0.1675 0.3031 0.048 Uiso 1 1 calc R . . . .


_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 P1 1.9485(5) . ?
P1 C6 1.8127(14) . ?
P1 C7 1.7828(15) . ?
P1 C12 1.8425(13) . ?
O1 N1 1.4644(14) . ?
O1 C11 1.4446(15) . ?
N1 C13 1.4824(16) . ?
N1 C14 1.4523(19) . ?
C1 H1 0.9300 . ?
C1 C2 1.392(2) . ?
C1 C6 1.392(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.327(2) . ?
C8 C9 1.503(2) . ?
C8 C11 1.5194(19) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 C11 1.517(2) . ?
C11 C12 1.5552(17) . ?
C12 H12 0.9800 . ?
C12 C13 1.5395(17) . ?
C13 H13 0.9800 . ?
C13 C15 1.5130(18) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.381(2) . ?
C15 C20 1.3860(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(2) . ?
C20 H20 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
C6 P1 S1 113.13(5) . . ?
C6 P1 C12 107.65(6) . . ?
C7 P1 S1 116.05(5) . . ?
C7 P1 C6 107.22(7) . . ?
C7 P1 C12 93.77(7) . . ?
C12 P1 S1 117.07(4) . . ?
C11 O1 N1 103.52(9) . . ?
O1 N1 C13 102.08(10) . . ?
C14 N1 O1 104.89(11) . . ?
C14 N1 C13 111.99(12) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.75(14) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.12(16) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.23(15) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.20(15) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.13(15) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 P1 120.54(10) . . ?
C5 C6 P1 119.86(11) . . ?
C5 C6 C1 119.57(13) . . ?
P1 C7 H7 123.1 . . ?
C8 C7 P1 113.78(11) . . ?
C8 C7 H7 123.1 . . ?
C7 C8 C9 125.26(15) . . ?
C7 C8 C11 116.05(12) . . ?
C9 C8 C11 118.65(14) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
O1 C11 C8 104.99(11) . . ?
O1 C11 C10 110.93(12) . . ?
O1 C11 C12 104.01(10) . . ?
C8 C11 C12 109.94(11) . . ?
C10 C11 C8 114.23(12) . . ?
C10 C11 C12 112.03(11) . . ?
P1 C12 H12 110.1 . . ?
C11 C12 P1 106.42(9) . . ?
C11 C12 H12 110.1 . . ?
C13 C12 P1 115.78(9) . . ?
C13 C12 C11 103.99(10) . . ?
C13 C12 H12 110.1 . . ?
N1 C13 C12 102.01(10) . . ?
N1 C13 H13 110.1 . . ?
N1 C13 C15 109.46(11) . . ?
C12 C13 H13 110.1 . . ?
C15 C13 C12 114.91(11) . . ?
C15 C13 H13 110.1 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 121.40(12) . . ?
C16 C15 C20 118.37(13) . . ?
C20 C15 C13 120.23(13) . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.79(15) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.29(16) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.66(15) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.11(15) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.76(15) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.285
_oxdiff_exptl_absorpt_empirical_full_min 0.759
