# Supplementary Information (SI) for Organic & Biomolecular 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_1
_database_code_depnum_ccdc_archive 'CCDC 2260087'
loop_
_audit_author_name
_audit_author_address
'ming li' 'Northwest Normal Law University'
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 N2 P'
_chemical_formula_sum            'C20 H15 N2 P'
_chemical_formula_weight         314.31
_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'
N N 0.0061 0.0033 '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'

_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                   6.0016(4)
_cell_length_b                   11.8760(7)
_cell_length_c                   11.5703(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.548(2)
_cell_angle_gamma                90
_cell_volume                     824.64(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1778
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      3.39
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0583 before and 0.0290 after correction.
The Ratio of minimum to maximum transmission is 0.8997.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4916
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.513
_diffrn_reflns_theta_min         3.395
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.775
_reflns_Friedel_fraction_max     0.693
_reflns_number_gt                2740
_reflns_number_total             3887
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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         0.150
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 890 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.034
_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)+(0.0330P)²+0.0707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.1008
_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:
 C004(H004), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), 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 0.55992(14) 0.67080(8) 0.30613(7) 0.0556(2) Uani 1 1 d . . . . .
N002 N 0.4817(4) 0.4631(2) 0.2657(2) 0.0503(6) Uani 1 1 d . . . . .
N003 N 0.3332(4) 0.5160(2) 0.1949(2) 0.0543(7) Uani 1 1 d . . . . .
C004 C 0.7366(6) 0.3982(3) 0.4899(3) 0.0547(8) Uani 1 1 d . . . . .
H004 H 0.604248 0.357956 0.482859 0.066 Uiso 1 1 calc R U . . .
C005 C 0.7788(5) 0.4880(2) 0.4163(3) 0.0457(7) Uani 1 1 d . . . . .
C006 C 0.3562(6) 0.6258(2) 0.2059(3) 0.0509(8) Uani 1 1 d . . . . .
C007 C 0.4863(5) 0.3419(2) 0.2588(3) 0.0507(8) Uani 1 1 d . . . . .
C008 C 0.6159(5) 0.5304(2) 0.3311(3) 0.0458(7) Uani 1 1 d . . . . .
C009 C 1.0887(6) 0.4274(3) 0.5854(3) 0.0639(9) Uani 1 1 d . . . . .
H009 H 1.192536 0.406353 0.641509 0.077 Uiso 1 1 calc R U . . .
C00A C 0.2593(8) 0.8139(3) 0.1274(3) 0.0753(11) Uani 1 1 d . . . . .
H00A H 0.392151 0.841283 0.158378 0.090 Uiso 1 1 calc R U . . .
C00B C 0.3066(6) 0.2823(3) 0.2984(3) 0.0671(10) Uani 1 1 d . . . . .
H00B H 0.184376 0.319230 0.329500 0.081 Uiso 1 1 calc R U . . .
C00C C 0.9787(5) 0.5465(3) 0.4301(3) 0.0553(8) Uani 1 1 d . . . . .
H00C H 1.010075 0.606750 0.381564 0.066 Uiso 1 1 calc R U . . .
C00D C 1.1301(5) 0.5161(3) 0.5145(3) 0.0643(9) Uani 1 1 d . . . . .
H00D H 1.261860 0.556606 0.523100 0.077 Uiso 1 1 calc R U . . .
C00E C 0.6672(6) 0.2899(3) 0.2131(3) 0.0663(9) Uani 1 1 d . . . . .
H00E H 0.788014 0.331491 0.186942 0.080 Uiso 1 1 calc R U . . .
C00F C 0.2075(6) 0.7010(3) 0.1393(3) 0.0549(8) Uani 1 1 d . . . . .
C00G C 0.8914(6) 0.3689(3) 0.5734(3) 0.0626(9) Uani 1 1 d . . . . .
H00G H 0.862328 0.308694 0.622387 0.075 Uiso 1 1 calc R U . . .
C00H C 0.0085(5) 0.6624(4) 0.0921(3) 0.0659(9) Uani 1 1 d . . . . .
H00H H -0.030261 0.586973 0.099578 0.079 Uiso 1 1 calc R U . . .
C00I C 0.6668(7) 0.1732(4) 0.2063(3) 0.0825(11) Uani 1 1 d . . . . .
H00I H 0.788630 0.135979 0.175176 0.099 Uiso 1 1 calc R U . . .
C00J C 0.3116(7) 0.1670(4) 0.2911(4) 0.0836(11) Uani 1 1 d . . . . .
H00J H 0.191645 0.125320 0.317944 0.100 Uiso 1 1 calc R U . . .
C00K C 0.4904(9) 0.1127(3) 0.2448(4) 0.0886(15) Uani 1 1 d . . . . .
H00K H 0.491307 0.034539 0.239620 0.106 Uiso 1 1 calc R U . . .
C00L C 0.1165(9) 0.8866(4) 0.0700(4) 0.0948(15) Uani 1 1 d . . . . .
H00L H 0.153618 0.962283 0.063108 0.114 Uiso 1 1 calc R U . . .
C00M C -0.1332(7) 0.7358(4) 0.0337(3) 0.0823(12) Uani 1 1 d . . . . .
H00M H -0.265516 0.709123 0.001400 0.099 Uiso 1 1 calc R U . . .
C00N C -0.0785(8) 0.8479(4) 0.0233(4) 0.0894(14) Uani 1 1 d . . . . .
H00N H -0.174174 0.897038 -0.015271 0.107 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 C006 1.760(3) . ?
P001 C008 1.725(3) . ?
N002 N003 1.359(3) . ?
N002 C007 1.442(4) . ?
N002 C008 1.360(4) . ?
N003 C006 1.318(4) . ?
C004 H004 0.9300 . ?
C004 C005 1.390(4) . ?
C004 C00G 1.378(4) . ?
C005 C008 1.471(4) . ?
C005 C00C 1.394(4) . ?
C006 C00F 1.475(4) . ?
C007 C00B 1.372(5) . ?
C007 C00E 1.360(5) . ?
C009 H009 0.9300 . ?
C009 C00D 1.360(5) . ?
C009 C00G 1.378(5) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.383(5) . ?
C00A C00L 1.381(5) . ?
C00B H00B 0.9300 . ?
C00B C00J 1.372(6) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.376(5) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00I 1.389(6) . ?
C00F C00H 1.386(5) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00H C00M 1.389(5) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.358(6) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.366(6) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00N 1.364(6) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.376(6) . ?
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
C008 P001 C006 87.13(15) . . ?
N003 N002 C007 116.2(2) . . ?
N003 N002 C008 116.5(3) . . ?
C008 N002 C007 127.3(3) . . ?
C006 N003 N002 109.4(3) . . ?
C005 C004 H004 120.1 . . ?
C00G C004 H004 120.1 . . ?
C00G C004 C005 119.8(3) . . ?
C004 C005 C008 123.3(3) . . ?
C004 C005 C00C 118.3(3) . . ?
C00C C005 C008 118.2(3) . . ?
N003 C006 P001 115.8(2) . . ?
N003 C006 C00F 119.1(3) . . ?
C00F C006 P001 125.0(2) . . ?
C00B C007 N002 118.7(3) . . ?
C00E C007 N002 119.3(3) . . ?
C00E C007 C00B 121.9(3) . . ?
N002 C008 P001 111.2(2) . . ?
N002 C008 C005 123.9(3) . . ?
C005 C008 P001 124.8(2) . . ?
C00D C009 H009 120.3 . . ?
C00D C009 C00G 119.4(3) . . ?
C00G C009 H009 120.3 . . ?
C00F C00A H00A 119.5 . . ?
C00L C00A H00A 119.5 . . ?
C00L C00A C00F 121.0(4) . . ?
C007 C00B H00B 120.8 . . ?
C007 C00B C00J 118.4(4) . . ?
C00J C00B H00B 120.8 . . ?
C005 C00C H00C 119.6 . . ?
C00D C00C C005 120.8(3) . . ?
C00D C00C H00C 119.6 . . ?
C009 C00D C00C 120.5(3) . . ?
C009 C00D H00D 119.7 . . ?
C00C C00D H00D 119.7 . . ?
C007 C00E H00E 120.9 . . ?
C007 C00E C00I 118.3(4) . . ?
C00I C00E H00E 120.9 . . ?
C00A C00F C006 120.2(3) . . ?
C00A C00F C00H 118.3(3) . . ?
C00H C00F C006 121.4(3) . . ?
C004 C00G C009 121.0(3) . . ?
C004 C00G H00G 119.5 . . ?
C009 C00G H00G 119.5 . . ?
C00F C00H H00H 119.8 . . ?
C00F C00H C00M 120.4(4) . . ?
C00M C00H H00H 119.8 . . ?
C00E C00I H00I 119.6 . . ?
C00K C00I C00E 120.7(4) . . ?
C00K C00I H00I 119.6 . . ?
C00B C00J H00J 119.6 . . ?
C00K C00J C00B 120.9(4) . . ?
C00K C00J H00J 119.6 . . ?
C00I C00K C00J 119.8(4) . . ?
C00I C00K H00K 120.1 . . ?
C00J C00K H00K 120.1 . . ?
C00A C00L H00L 119.8 . . ?
C00N C00L C00A 120.4(4) . . ?
C00N C00L H00L 119.8 . . ?
C00H C00M H00M 119.9 . . ?
C00N C00M C00H 120.3(4) . . ?
C00N C00M H00M 119.9 . . ?
C00L C00N C00M 119.7(4) . . ?
C00L C00N H00N 120.1 . . ?
C00M C00N H00N 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
P001 C006 C00F C00A 18.2(5) . . . . ?
P001 C006 C00F C00H -158.7(3) . . . . ?
N002 N003 C006 P001 -1.0(4) . . . . ?
N002 N003 C006 C00F -178.4(3) . . . . ?
N002 C007 C00B C00J 179.7(3) . . . . ?
N002 C007 C00E C00I -179.4(3) . . . . ?
N003 N002 C007 C00B -68.7(4) . . . . ?
N003 N002 C007 C00E 111.0(3) . . . . ?
N003 N002 C008 P001 0.0(3) . . . . ?
N003 N002 C008 C005 177.1(3) . . . . ?
N003 C006 C00F C00A -164.7(4) . . . . ?
N003 C006 C00F C00H 18.4(5) . . . . ?
C004 C005 C008 P001 136.2(3) . . . . ?
C004 C005 C008 N002 -40.5(5) . . . . ?
C004 C005 C00C C00D -0.1(5) . . . . ?
C005 C004 C00G C009 0.0(5) . . . . ?
C005 C00C C00D C009 0.8(5) . . . . ?
C006 P001 C008 N002 -0.5(2) . . . . ?
C006 P001 C008 C005 -177.5(3) . . . . ?
C006 C00F C00H C00M 177.4(3) . . . . ?
C007 N002 N003 C006 -176.6(3) . . . . ?
C007 N002 C008 P001 176.8(3) . . . . ?
C007 N002 C008 C005 -6.1(5) . . . . ?
C007 C00B C00J C00K -0.4(6) . . . . ?
C007 C00E C00I C00K -0.2(6) . . . . ?
C008 P001 C006 N003 0.8(3) . . . . ?
C008 P001 C006 C00F 178.1(3) . . . . ?
C008 N002 N003 C006 0.6(4) . . . . ?
C008 N002 C007 C00B 114.5(4) . . . . ?
C008 N002 C007 C00E -65.8(5) . . . . ?
C008 C005 C00C C00D 174.9(3) . . . . ?
C00A C00F C00H C00M 0.5(5) . . . . ?
C00A C00L C00N C00M 0.0(7) . . . . ?
C00B C007 C00E C00I 0.3(5) . . . . ?
C00B C00J C00K C00I 0.6(6) . . . . ?
C00C C005 C008 P001 -38.6(4) . . . . ?
C00C C005 C008 N002 144.8(3) . . . . ?
C00D C009 C00G C004 0.7(5) . . . . ?
C00E C007 C00B C00J 0.0(5) . . . . ?
C00E C00I C00K C00J -0.3(6) . . . . ?
C00F C00A C00L C00N -0.4(8) . . . . ?
C00F C00H C00M C00N -0.8(6) . . . . ?
C00G C004 C005 C008 -175.1(3) . . . . ?
C00G C004 C005 C00C -0.3(5) . . . . ?
C00G C009 C00D C00C -1.1(5) . . . . ?
C00H C00M C00N C00L 0.5(7) . . . . ?
C00L C00A C00F C006 -176.9(4) . . . . ?
C00L C00A C00F C00H 0.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
