# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_LM-01-169
_database_code_depnum_ccdc_archive 'CCDC 2332940'
loop_
_audit_author_name
_audit_author_address
'Sonia Mallet-Ladeira'
;Universite Paul Sabatier
France
;
_audit_update_record             
;
2024-02-14 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C26 H19 O P'
_chemical_formula_sum            'C26 H19 O P'
_chemical_formula_weight         378.38

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5610(7)
_cell_length_b                   8.7992(7)
_cell_length_c                   23.2962(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.14(3)
_cell_angle_gamma                90
_cell_volume                     1959.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.43

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             792

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6683
_exptl_absorpt_correction_T_max  0.7454

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  triumph
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_number            27187
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.146
_diffrn_reflns_theta_max         26.435
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.97
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.97
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.97
_reflns_Friedel_coverage         0
_reflns_number_total             3910
_reflns_number_gt                3533
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2019/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+0.6121P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3910
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
C1 C 0.72540(13) 0.27936(16) 0.40167(6) 0.0330(3) Uani 1 1 d . . . . .
C2 C 0.81584(15) 0.31167(18) 0.44685(7) 0.0414(3) Uani 1 1 d . . . . .
H2 H 0.786044 0.372039 0.478335 0.05 Uiso 1 1 calc R U . . .
C3 C 0.95200(16) 0.2531(2) 0.44484(8) 0.0515(4) Uani 1 1 d . . . . .
H3 H 1.015417 0.273288 0.475359 0.062 Uiso 1 1 calc R U . . .
C4 C 0.99475(16) 0.1656(2) 0.39840(8) 0.0541(5) Uani 1 1 d . . . . .
H4 H 1.08732 0.12641 0.397586 0.065 Uiso 1 1 calc R U . . .
C5 C 0.90409(16) 0.1344(2) 0.35310(7) 0.0469(4) Uani 1 1 d . . . . .
H5 H 0.934558 0.074911 0.321491 0.056 Uiso 1 1 calc R U . . .
C6 C 0.76844(14) 0.19127(17) 0.35454(6) 0.0359(3) Uani 1 1 d . . . . .
C7 C 0.65904(15) 0.17152(16) 0.31075(6) 0.0355(3) Uani 1 1 d . . . . .
H7 H 0.673803 0.112773 0.27709 0.043 Uiso 1 1 calc R U . . .
C8 C 0.53597(13) 0.24214(15) 0.32129(5) 0.0302(3) Uani 1 1 d . . . . .
C9 C 0.40899(13) 0.24284(15) 0.28592(5) 0.0305(3) Uani 1 1 d . . . . .
C10 C 0.40034(16) 0.16953(19) 0.23268(7) 0.0428(4) Uani 1 1 d . . . . .
H10 H 0.48063 0.120052 0.217665 0.051 Uiso 1 1 calc R U . . .
C11 C 0.27680(16) 0.1679(2) 0.20154(6) 0.0445(4) Uani 1 1 d . . . . .
H11 H 0.274576 0.117607 0.165466 0.053 Uiso 1 1 calc R U . . .
C12 C 0.15500(14) 0.23822(16) 0.22169(5) 0.0319(3) Uani 1 1 d . . . . .
C13 C 0.16564(15) 0.31593(18) 0.27373(6) 0.0383(3) Uani 1 1 d . . . . .
H13 H 0.086215 0.36831 0.288102 0.046 Uiso 1 1 calc R U . . .
C14 C 0.28923(15) 0.31864(17) 0.30501(6) 0.0367(3) Uani 1 1 d . . . . .
H14 H 0.292617 0.373183 0.340174 0.044 Uiso 1 1 calc R U . . .
C15 C 0.01980(14) 0.22950(16) 0.18976(6) 0.0348(3) Uani 1 1 d . . . . .
C16 C 0.00204(18) 0.12886(19) 0.14366(7) 0.0441(4) Uani 1 1 d . . . . .
H16 H 0.078128 0.067247 0.131649 0.053 Uiso 1 1 calc R U . . .
C17 C -0.12593(19) 0.1183(2) 0.11529(7) 0.0538(4) Uani 1 1 d . . . . .
H17 H -0.135871 0.049384 0.084147 0.065 Uiso 1 1 calc R U . . .
C18 C -0.23851(18) 0.2060(2) 0.13163(8) 0.0536(5) Uani 1 1 d . . . . .
H18 H -0.325666 0.197294 0.112237 0.064 Uiso 1 1 calc R U . . .
C19 C -0.22260(17) 0.3071(2) 0.17671(8) 0.0507(4) Uani 1 1 d . . . . .
H19 H -0.299081 0.368906 0.18814 0.061 Uiso 1 1 calc R U . . .
C20 C -0.09531(16) 0.31863(19) 0.20536(7) 0.0431(4) Uani 1 1 d . . . . .
H20 H -0.086239 0.388552 0.236217 0.052 Uiso 1 1 calc R U . . .
C21 C 0.43803(12) 0.23111(15) 0.43989(5) 0.0289(3) Uani 1 1 d . . . . .
C22 C 0.38959(17) 0.30614(19) 0.48830(7) 0.0454(4) Uani 1 1 d . . . . .
H22 H 0.412691 0.40997 0.494238 0.054 Uiso 1 1 calc R U . . .
C23 C 0.30747(18) 0.2300(2) 0.52812(7) 0.0516(4) Uani 1 1 d . . . . .
H23 H 0.275976 0.281574 0.561507 0.062 Uiso 1 1 calc R U . . .
C24 C 0.27153(15) 0.08057(19) 0.51946(6) 0.0417(3) Uani 1 1 d . . . . .
H24 H 0.214583 0.029103 0.546586 0.05 Uiso 1 1 calc R U . . .
C25 C 0.31853(17) 0.00557(18) 0.47120(7) 0.0425(3) Uani 1 1 d . . . . .
H25 H 0.293402 -0.097659 0.465151 0.051 Uiso 1 1 calc R U . . .
C26 C 0.40206(15) 0.07946(16) 0.43149(6) 0.0366(3) Uani 1 1 d . . . . .
H26 H 0.434719 0.02668 0.398572 0.044 Uiso 1 1 calc R U . . .
O1 O 0.51949(10) 0.50302(11) 0.39400(4) 0.0360(2) Uani 1 1 d . . . . .
P1 P 0.54648(3) 0.33703(4) 0.39081(2) 0.02800(13) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.390(2) . ?
C1 C6 1.406(2) . ?
C1 P1 1.8016(13) . ?
C2 C3 1.401(2) . ?
C2 H2 0.95 . ?
C3 C4 1.390(3) . ?
C3 H3 0.95 . ?
C4 C5 1.391(3) . ?
C4 H4 0.95 . ?
C5 C6 1.391(2) . ?
C5 H5 0.95 . ?
C6 C7 1.470(2) . ?
C7 C8 1.3537(19) . ?
C7 H7 0.95 . ?
C8 C9 1.4656(18) . ?
C8 P1 1.8247(13) . ?
C9 C14 1.3987(19) . ?
C9 C10 1.4001(19) . ?
C10 C11 1.385(2) . ?
C10 H10 0.95 . ?
C11 C12 1.401(2) . ?
C11 H11 0.95 . ?
C12 C13 1.395(2) . ?
C12 C15 1.4918(18) . ?
C13 C14 1.387(2) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 C20 1.400(2) . ?
C15 C16 1.402(2) . ?
C16 C17 1.392(2) . ?
C16 H16 0.95 . ?
C17 C18 1.379(3) . ?
C17 H17 0.95 . ?
C18 C19 1.384(3) . ?
C18 H18 0.95 . ?
C19 C20 1.390(2) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
C21 C22 1.387(2) . ?
C21 C26 1.392(2) . ?
C21 P1 1.8047(14) . ?
C22 C23 1.389(2) . ?
C22 H22 0.95 . ?
C23 C24 1.374(2) . ?
C23 H23 0.95 . ?
C24 C25 1.380(2) . ?
C24 H24 0.95 . ?
C25 C26 1.386(2) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
O1 P1 1.4852(10) . ?

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
C2 C1 C6 121.41(13) . . ?
C2 C1 P1 129.61(12) . . ?
C6 C1 P1 108.97(10) . . ?
C1 C2 C3 118.42(16) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 120.31(16) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.03(15) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.36(17) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 119.46(14) . . ?
C5 C6 C7 127.08(15) . . ?
C1 C6 C7 113.46(12) . . ?
C8 C7 C6 115.93(13) . . ?
C8 C7 H7 122 . . ?
C6 C7 H7 122 . . ?
C7 C8 C9 128.25(12) . . ?
C7 C8 P1 108.97(10) . . ?
C9 C8 P1 122.74(10) . . ?
C14 C9 C10 117.05(13) . . ?
C14 C9 C8 120.06(12) . . ?
C10 C9 C8 122.89(12) . . ?
C11 C10 C9 121.15(14) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 121.91(13) . . ?
C10 C11 H11 119 . . ?
C12 C11 H11 119 . . ?
C13 C12 C11 116.67(13) . . ?
C13 C12 C15 121.31(13) . . ?
C11 C12 C15 122.02(13) . . ?
C14 C13 C12 121.67(13) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C9 121.46(13) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C20 C15 C16 117.31(14) . . ?
C20 C15 C12 121.50(13) . . ?
C16 C15 C12 121.18(14) . . ?
C17 C16 C15 120.70(16) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 121.13(17) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 118.99(15) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C20 120.38(17) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 121.48(16) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
C22 C21 C26 119.19(13) . . ?
C22 C21 P1 117.56(11) . . ?
C26 C21 P1 123.25(10) . . ?
C21 C22 C23 120.25(15) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.34(14) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.71(14) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.59(14) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 119.91(13) . . ?
C25 C26 H26 120 . . ?
C21 C26 H26 120 . . ?
O1 P1 C1 115.78(6) . . ?
O1 P1 C21 112.09(6) . . ?
C1 P1 C21 108.20(6) . . ?
O1 P1 C8 119.03(6) . . ?
C1 P1 C8 92.63(7) . . ?
C21 P1 C8 107.19(6) . . ?




# END of CIF
