# Electronic Supplementary Material (ESI) 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_ljl-hh-0924
_database_code_depnum_ccdc_archive 'CCDC 2313314'
loop_
_audit_author_name
_audit_author_address
'Hua Huang'
;Chengdu university of TCM
China
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_audit_creation_date             2022-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Cl O2 P'
_chemical_formula_sum            'C22 H20 Cl O2 P'
_chemical_formula_weight         382.80
_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'
Cl Cl 0.3639 0.7018 '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'

_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                   5.74906(11)
_cell_length_b                   19.4433(5)
_cell_length_c                   17.5592(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.9972(18)
_cell_angle_gamma                90
_cell_volume                     1958.00(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3591
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.0920
_cell_measurement_theta_min      5.1690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10742
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.318
_diffrn_reflns_theta_min         4.548
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00   3.00   1.00    4.68    --  -34.98 -19.00 150.00  110
  2  ω     23.00  90.00   1.00    4.68    --   34.98-125.00  30.00   67
  3  ω    -33.00  53.00   1.00    4.68    --   34.98 -57.00  60.00   86
  4  ω      6.00 104.00   1.00    4.68    --   34.98  77.00 -90.00   98
  5  ω      1.00  75.00   1.00    4.68    --   34.98 -99.00-120.00   74
  6  ω     13.00 106.00   1.00    4.68    --   34.98  38.00  30.00   93
  7  ω     87.00 177.00   1.00   18.73    --  106.90  45.00-120.00   90
  8  ω     36.00 113.00   1.00   18.73    --  106.90-111.00 -90.00   77
  9  ω    100.00 178.00   1.00   18.73    --  106.90 111.00 150.00   78
 10  ω     36.00 113.00   1.00   18.73    --  106.90-111.00-120.00   77
 11  ω     81.00 178.00   1.00   18.73    --  106.90  30.00-150.00   97
 12  ω     36.00 113.00   1.00   18.73    --  106.90-111.00  60.00   77
 13  ω     81.00 178.00   1.00   18.73    --  106.90  30.00 -60.00   97
 14  ω     41.00 110.00   1.00   18.73    --  106.90 -94.00  90.00   69
 15  ω     44.00 126.00   1.00   18.73    --  106.90 -45.00  60.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0237675000
_diffrn_orient_matrix_UB_12      -0.0453122000
_diffrn_orient_matrix_UB_13      0.0720600000
_diffrn_orient_matrix_UB_21      -0.0339780000
_diffrn_orient_matrix_UB_22      0.0638682000
_diffrn_orient_matrix_UB_23      0.0499998000
_diffrn_orient_matrix_UB_31      -0.2654000000
_diffrn_orient_matrix_UB_32      -0.0122243000
_diffrn_orient_matrix_UB_33      -0.0061534000
_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                3033
_reflns_number_total             3732
_reflns_odcompleteness_completeness 99.92
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.458
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3732
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      1.019
_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)+(0.1300P)²+0.2018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1865
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00C(H00C,H00D), C00I(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00D(H00E), C00E(H00F), C00F(H00G),
 C00H(H00H), C00J(H00K), C00K(H00L), C00L(H00M), C00M(H00N), C00N(H00O),
 C00O(H00P), C00P(H00Q), C00Q(H00R)
2.c Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_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
P01 P 0.70377(9) 0.49699(3) 0.67821(3) 0.0410(2) Uani 1 1 d . . . . .
Cl02 Cl 0.4808(2) 0.94289(5) 0.58218(7) 0.0972(4) Uani 1 1 d . . . . .
O003 O 0.4532(3) 0.50518(9) 0.65182(10) 0.0504(4) Uani 1 1 d . . . . .
O004 O 0.3490(3) 0.58138(12) 0.51728(12) 0.0648(5) Uani 1 1 d . . . . .
H004 H 0.3625 0.5618 0.5587 0.097 Uiso 1 1 calc GR . . . .
C005 C 0.6548(4) 0.71717(13) 0.56403(12) 0.0450(5) Uani 1 1 d . . . . .
C006 C 0.7058(4) 0.64248(13) 0.55891(12) 0.0436(5) Uani 1 1 d . . . . .
C007 C 0.7669(4) 0.54028(13) 0.76861(13) 0.0470(5) Uani 1 1 d . . . . .
C008 C 0.7840(4) 0.40752(13) 0.69014(13) 0.0464(5) Uani 1 1 d . . . . .
C009 C 0.8122(4) 0.76327(14) 0.59953(15) 0.0539(6) Uani 1 1 d . . . . .
H009 H 0.9563 0.7473 0.6195 0.065 Uiso 1 1 calc R . . . .
C00A C 0.6043(5) 0.58701(17) 0.79146(17) 0.0623(7) Uani 1 1 d . . . . .
H00A H 0.4667 0.5944 0.7615 0.075 Uiso 1 1 calc R . . . .
C00B C 0.8530(4) 0.61104(13) 0.60956(13) 0.0461(5) Uani 1 1 d . . . . .
H00B H 0.9335 0.6389 0.6455 0.055 Uiso 1 1 calc R . . . .
C00C C 0.5727(5) 0.60234(14) 0.49611(14) 0.0534(6) Uani 1 1 d . . . . .
H00C H 0.5542 0.6306 0.4506 0.064 Uiso 1 1 calc R . . . .
H00D H 0.6621 0.5620 0.4840 0.064 Uiso 1 1 calc R . . . .
C00D C 0.3897(5) 0.81250(17) 0.5400(2) 0.0679(8) Uani 1 1 d . . . . .
H00E H 0.2466 0.8292 0.5201 0.081 Uiso 1 1 calc R . . . .
C00E C 0.9710(5) 0.52958(17) 0.81305(17) 0.0627(7) Uani 1 1 d . . . . .
H00F H 1.0818 0.4986 0.7977 0.075 Uiso 1 1 calc R . . . .
C00F C 0.4432(5) 0.74335(15) 0.53391(17) 0.0589(6) Uani 1 1 d . . . . .
H00G H 0.3354 0.7139 0.5091 0.071 Uiso 1 1 calc R . . . .
C00G C 0.5498(6) 0.85621(15) 0.57587(16) 0.0622(7) Uani 1 1 d . . . . .
C00H C 0.7594(6) 0.83245(16) 0.60592(17) 0.0639(7) Uani 1 1 d . . . . .
H00H H 0.8662 0.8624 0.6305 0.077 Uiso 1 1 calc R . . . .
C00I C 0.9019(4) 0.53565(13) 0.61442(14) 0.0476(5) Uani 1 1 d . . . . .
H00I H 1.0620 0.5279 0.6337 0.057 Uiso 1 1 calc R . . . .
H00J H 0.8797 0.5150 0.5642 0.057 Uiso 1 1 calc R . . . .
C00J C 0.8475(6) 0.6121(2) 0.90302(19) 0.0822(11) Uani 1 1 d . . . . .
H00K H 0.8752 0.6365 0.9483 0.099 Uiso 1 1 calc R . . . .
C00K C 1.0087(6) 0.5657(2) 0.8810(2) 0.0810(10) Uani 1 1 d . . . . .
H00L H 1.1447 0.5583 0.9118 0.097 Uiso 1 1 calc R . . . .
C00L C 0.6384(5) 0.36549(17) 0.72824(19) 0.0670(7) Uani 1 1 d . . . . .
H00M H 0.5089 0.3842 0.7495 0.080 Uiso 1 1 calc R . . . .
C00M C 0.8720(7) 0.26732(17) 0.7039(2) 0.0764(9) Uani 1 1 d . . . . .
H00N H 0.9011 0.2204 0.7079 0.092 Uiso 1 1 calc R . . . .
C00N C 0.9762(6) 0.37924(18) 0.6599(2) 0.0792(10) Uani 1 1 d . . . . .
H00O H 1.0784 0.4071 0.6350 0.095 Uiso 1 1 calc R . . . .
C00O C 0.6472(6) 0.6227(2) 0.8589(2) 0.0796(10) Uani 1 1 d . . . . .
H00P H 0.5382 0.6542 0.8743 0.096 Uiso 1 1 calc R . . . .
C00P C 0.6820(7) 0.29592(18) 0.7352(2) 0.0799(9) Uani 1 1 d . . . . .
H00Q H 0.5823 0.2682 0.7613 0.096 Uiso 1 1 calc R . . . .
C00Q C 1.0177(7) 0.3094(2) 0.6665(3) 0.0915(12) Uani 1 1 d . . . . .
H00R H 1.1470 0.2906 0.6452 0.110 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
P01 O003 1.4909(17) . ?
P01 C007 1.811(2) . ?
P01 C008 1.808(3) . ?
P01 C00I 1.815(2) . ?
Cl02 C00G 1.737(3) . ?
O004 H004 0.8200 . ?
O004 C00C 1.423(3) . ?
C005 C006 1.486(3) . ?
C005 C009 1.390(4) . ?
C005 C00F 1.389(3) . ?
C006 C00B 1.333(3) . ?
C006 C00C 1.514(3) . ?
C007 C00A 1.383(4) . ?
C007 C00E 1.379(4) . ?
C008 C00L 1.376(4) . ?
C008 C00N 1.374(4) . ?
C009 H009 0.9300 . ?
C009 C00H 1.385(4) . ?
C00A H00A 0.9300 . ?
C00A C00O 1.380(4) . ?
C00B H00B 0.9300 . ?
C00B C00I 1.494(4) . ?
C00C H00C 0.9700 . ?
C00C H00D 0.9700 . ?
C00D H00E 0.9300 . ?
C00D C00F 1.385(4) . ?
C00D C00G 1.373(5) . ?
C00E H00F 0.9300 . ?
C00E C00K 1.388(4) . ?
C00F H00G 0.9300 . ?
C00G C00H 1.362(5) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9700 . ?
C00I H00J 0.9700 . ?
C00J H00K 0.9300 . ?
C00J C00K 1.369(5) . ?
C00J C00O 1.357(5) . ?
C00K H00L 0.9300 . ?
C00L H00M 0.9300 . ?
C00L C00P 1.380(5) . ?
C00M H00N 0.9300 . ?
C00M C00P 1.375(5) . ?
C00M C00Q 1.370(5) . ?
C00N H00O 0.9300 . ?
C00N C00Q 1.382(5) . ?
C00O H00P 0.9300 . ?
C00P H00Q 0.9300 . ?
C00Q H00R 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 P01 C007 110.68(11) . . ?
O003 P01 C008 111.83(11) . . ?
O003 P01 C00I 113.48(10) . . ?
C007 P01 C00I 104.61(12) . . ?
C008 P01 C007 108.16(11) . . ?
C008 P01 C00I 107.70(11) . . ?
C00C O004 H004 109.5 . . ?
C009 C005 C006 122.2(2) . . ?
C00F C005 C006 120.4(2) . . ?
C00F C005 C009 117.4(2) . . ?
C005 C006 C00C 117.1(2) . . ?
C00B C006 C005 121.8(2) . . ?
C00B C006 C00C 121.0(2) . . ?
C00A C007 P01 117.5(2) . . ?
C00E C007 P01 122.5(2) . . ?
C00E C007 C00A 120.0(3) . . ?
C00L C008 P01 118.0(2) . . ?
C00N C008 P01 123.1(2) . . ?
C00N C008 C00L 118.9(3) . . ?
C005 C009 H009 119.2 . . ?
C00H C009 C005 121.5(2) . . ?
C00H C009 H009 119.2 . . ?
C007 C00A H00A 120.2 . . ?
C00O C00A C007 119.7(3) . . ?
C00O C00A H00A 120.2 . . ?
C006 C00B H00B 116.7 . . ?
C006 C00B C00I 126.6(2) . . ?
C00I C00B H00B 116.7 . . ?
O004 C00C C006 112.2(2) . . ?
O004 C00C H00C 109.2 . . ?
O004 C00C H00D 109.2 . . ?
C006 C00C H00C 109.2 . . ?
C006 C00C H00D 109.2 . . ?
H00C C00C H00D 107.9 . . ?
C00F C00D H00E 120.3 . . ?
C00G C00D H00E 120.3 . . ?
C00G C00D C00F 119.4(3) . . ?
C007 C00E H00F 120.5 . . ?
C007 C00E C00K 119.1(3) . . ?
C00K C00E H00F 120.5 . . ?
C005 C00F H00G 119.3 . . ?
C00D C00F C005 121.3(3) . . ?
C00D C00F H00G 119.3 . . ?
C00D C00G Cl02 118.8(2) . . ?
C00H C00G Cl02 120.3(3) . . ?
C00H C00G C00D 120.9(3) . . ?
C009 C00H H00H 120.3 . . ?
C00G C00H C009 119.4(3) . . ?
C00G C00H H00H 120.3 . . ?
P01 C00I H00I 110.0 . . ?
P01 C00I H00J 110.0 . . ?
C00B C00I P01 108.54(16) . . ?
C00B C00I H00I 110.0 . . ?
C00B C00I H00J 110.0 . . ?
H00I C00I H00J 108.4 . . ?
C00K C00J H00K 119.9 . . ?
C00O C00J H00K 119.9 . . ?
C00O C00J C00K 120.2(3) . . ?
C00E C00K H00L 119.7 . . ?
C00J C00K C00E 120.5(3) . . ?
C00J C00K H00L 119.7 . . ?
C008 C00L H00M 119.6 . . ?
C008 C00L C00P 120.8(3) . . ?
C00P C00L H00M 119.6 . . ?
C00P C00M H00N 120.7 . . ?
C00Q C00M H00N 120.7 . . ?
C00Q C00M C00P 118.6(3) . . ?
C008 C00N H00O 120.0 . . ?
C008 C00N C00Q 120.0(3) . . ?
C00Q C00N H00O 120.0 . . ?
C00A C00O H00P 119.8 . . ?
C00J C00O C00A 120.5(3) . . ?
C00J C00O H00P 119.8 . . ?
C00L C00P H00Q 119.8 . . ?
C00M C00P C00L 120.4(3) . . ?
C00M C00P H00Q 119.8 . . ?
C00M C00Q C00N 121.3(3) . . ?
C00M C00Q H00R 119.4 . . ?
C00N C00Q H00R 119.4 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.644
