# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_1600
_database_code_depnum_ccdc_archive 'CCDC 2432548'
loop_
_audit_author_name
_audit_author_address
'Kosuke Katagiri'
;Konan University
Japan
;
_audit_update_record             
;
2025-03-19 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;
_audit_creation_date             2024-11-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H23 O P'
_chemical_formula_sum            'C32 H23 O P'
_chemical_formula_weight         454.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         C32H23OP
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'
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/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                   9.66347(14)
_cell_length_b                   27.2681(3)
_cell_length_c                   9.86176(18)
_cell_angle_alpha                90
_cell_angle_beta                 115.374(2)
_cell_angle_gamma                90
_cell_volume                     2347.92(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7181
_cell_measurement_temperature    173
_cell_measurement_theta_max      76.9550
_cell_measurement_theta_min      5.3270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.205
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13374
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.239
_diffrn_reflns_theta_min         5.222
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00  71.00   0.50    2.35    --    0.00  57.00   0.00   86
  2  ω     34.00  77.00   0.50    2.35    --    0.00  57.00 120.00   86
  3  ω    -22.00  31.00   0.50    2.35    --    0.00  57.00 120.00  106
  4  ω    -20.00  21.00   0.50    2.35    --    0.00  57.00   0.00   82
  5  ω     61.00 128.00   0.50    9.39    --  101.00 -61.00 -90.00  134
  6  ω     73.00 146.00   0.50    9.39    --  101.00  61.00 150.00  146
  7  ω     13.00  55.00   0.50    9.39    --  101.00 -77.00 -60.00   84
  8  ω    124.00 160.00   0.50    9.39    --  101.00  61.00  60.00   72
  9  ω     78.00 116.00   0.50    9.39    --  101.00  61.00  60.00   76
 10  ω     62.00 131.00   0.50    9.39    --  101.00 -77.00 -60.00  138
 11  ω     75.00 190.00   0.50    9.39    --  101.00  61.00  90.00  230
 12  ω     64.00  92.00   0.50    9.39    --  101.00 -30.00  30.00   56
 13  ω    118.00 183.00   0.50    9.39    --  101.00  45.00 150.00  130
 14  ω     90.00 115.00   0.50    9.39    --  101.00 -61.00-180.00   50
 15  ω     17.00  42.00   0.50    9.39    --  101.00 -30.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0318245000
_diffrn_orient_matrix_UB_12      0.0522074000
_diffrn_orient_matrix_UB_13      -0.0392959000
_diffrn_orient_matrix_UB_21      0.1703328000
_diffrn_orient_matrix_UB_22      -0.0131082000
_diffrn_orient_matrix_UB_23      0.0528683000
_diffrn_orient_matrix_UB_31      -0.0332877000
_diffrn_orient_matrix_UB_32      -0.0171609000
_diffrn_orient_matrix_UB_33      -0.1598564000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4340
_reflns_number_total             4795
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.059
_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)+(0.0370P)²+0.9338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0952
_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:
 C26(H26), C14(H14), C6(H6), C5(H5), C9(H9), C22(H22), C2(H2), C19(H19),
 C3(H3), C10(H10), C32(H32), C16(H16), C12(H12), C11(H11), C17(H17), C24(H24),
 C31(H31), C23(H23), C28(H28), C25(H25), C30(H30), C18(H18), C29(H29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
P1 P 0.75852(4) 0.40348(2) 0.64946(4) 0.02430(10) Uani 1 1 d . . . . .
O1 O 0.69659(12) 0.41529(4) 0.48736(11) 0.0331(2) Uani 1 1 d . . . . .
C7 C 0.46886(15) 0.21353(5) 0.72778(15) 0.0251(3) Uani 1 1 d . . . . .
C21 C 0.70822(15) 0.44880(5) 0.75416(15) 0.0259(3) Uani 1 1 d . . . . .
C15 C 0.23488(15) 0.17344(5) 0.71263(15) 0.0273(3) Uani 1 1 d . . . . .
C4 C 0.54993(14) 0.25876(5) 0.71549(15) 0.0249(3) Uani 1 1 d . . . . .
C27 C 0.96406(15) 0.39651(5) 0.73496(16) 0.0268(3) Uani 1 1 d . . . . .
C8 C 0.54531(15) 0.16803(5) 0.76199(15) 0.0259(3) Uani 1 1 d . . . . .
C13 C 0.46215(16) 0.12453(5) 0.76307(15) 0.0273(3) Uani 1 1 d . . . . .
C20 C 0.31468(15) 0.21705(5) 0.70441(15) 0.0262(3) Uani 1 1 d . . . . .
C26 C 0.80370(17) 0.46480(5) 0.89795(17) 0.0336(3) Uani 1 1 d . . . . .
H26 H 0.904494 0.451996 0.948182 0.040 Uiso 1 1 calc R U . . .
C14 C 0.30957(16) 0.12830(5) 0.73922(15) 0.0293(3) Uani 1 1 d . . . . .
H14 H 0.255269 0.099463 0.741117 0.035 Uiso 1 1 calc R U . . .
C6 C 0.65174(16) 0.30903(5) 0.57811(16) 0.0290(3) Uani 1 1 d . . . . .
H6 H 0.675548 0.313276 0.494845 0.035 Uiso 1 1 calc R U . . .
C1 C 0.68354(14) 0.34653(5) 0.68328(15) 0.0242(3) Uani 1 1 d . . . . .
C5 C 0.58566(16) 0.26561(5) 0.59404(16) 0.0293(3) Uani 1 1 d . . . . .
H5 H 0.564552 0.240309 0.521625 0.035 Uiso 1 1 calc R U . . .
C9 C 0.70579(16) 0.16328(5) 0.80070(16) 0.0305(3) Uani 1 1 d . . . . .
H9 H 0.764182 0.191775 0.805234 0.037 Uiso 1 1 calc R U . . .
C22 C 0.56058(16) 0.46824(5) 0.68171(17) 0.0325(3) Uani 1 1 d . . . . .
H22 H 0.494784 0.457558 0.583264 0.039 Uiso 1 1 calc R U . . .
C2 C 0.65118(16) 0.33935(5) 0.80664(15) 0.0286(3) Uani 1 1 d . . . . .
H2 H 0.674493 0.364336 0.880327 0.034 Uiso 1 1 calc R U . . .
C19 C 0.23186(17) 0.26231(5) 0.67026(17) 0.0322(3) Uani 1 1 d . . . . .
H19 H 0.281042 0.291393 0.660656 0.039 Uiso 1 1 calc R U . . .
C3 C 0.58502(16) 0.29583(5) 0.82214(16) 0.0286(3) Uani 1 1 d . . . . .
H3 H 0.563387 0.291268 0.906616 0.034 Uiso 1 1 calc R U . . .
C10 C 0.77579(17) 0.11872(6) 0.83101(17) 0.0350(3) Uani 1 1 d . . . . .
H10 H 0.882392 0.116530 0.857478 0.042 Uiso 1 1 calc R U . . .
C32 C 1.04403(16) 0.37377(5) 0.87307(17) 0.0319(3) Uani 1 1 d . . . . .
H32 H 0.991017 0.362875 0.929358 0.038 Uiso 1 1 calc R U . . .
C16 C 0.07996(16) 0.17766(6) 0.69212(16) 0.0330(3) Uani 1 1 d . . . . .
H16 H 0.026735 0.149134 0.698699 0.040 Uiso 1 1 calc R U . . .
C12 C 0.53994(18) 0.07842(5) 0.79161(17) 0.0335(3) Uani 1 1 d . . . . .
H12 H 0.484802 0.049253 0.788231 0.040 Uiso 1 1 calc R U . . .
C11 C 0.69108(19) 0.07547(6) 0.82348(17) 0.0369(3) Uani 1 1 d . . . . .
H11 H 0.740173 0.044398 0.840751 0.044 Uiso 1 1 calc R U . . .
C17 C 0.00702(17) 0.22171(6) 0.66335(17) 0.0369(3) Uani 1 1 d . . . . .
H17 H -0.095740 0.223745 0.651352 0.044 Uiso 1 1 calc R U . . .
C24 C 0.60470(19) 0.51824(6) 0.89539(19) 0.0385(3) Uani 1 1 d . . . . .
H24 H 0.569337 0.541747 0.944367 0.046 Uiso 1 1 calc R U . . .
C31 C 1.20091(18) 0.36696(6) 0.92871(19) 0.0381(3) Uani 1 1 d . . . . .
H31 H 1.255443 0.351790 1.023650 0.046 Uiso 1 1 calc R U . . .
C23 C 0.50941(18) 0.50292(6) 0.75216(19) 0.0376(3) Uani 1 1 d . . . . .
H23 H 0.409105 0.516109 0.702091 0.045 Uiso 1 1 calc R U . . .
C28 C 1.04327(18) 0.41213(6) 0.65338(18) 0.0367(3) Uani 1 1 d . . . . .
H28 H 0.989805 0.427785 0.559063 0.044 Uiso 1 1 calc R U . . .
C25 C 0.75154(19) 0.49954(6) 0.96814(18) 0.0392(4) Uani 1 1 d . . . . .
H25 H 0.816869 0.510505 1.066388 0.047 Uiso 1 1 calc R U . . .
C30 C 1.27796(18) 0.38217(6) 0.8465(2) 0.0416(4) Uani 1 1 d . . . . .
H30 H 1.385245 0.376988 0.884345 0.050 Uiso 1 1 calc R U . . .
C18 C 0.08363(17) 0.26451(6) 0.65123(18) 0.0373(3) Uani 1 1 d . . . . .
H18 H 0.031366 0.295064 0.629630 0.045 Uiso 1 1 calc R U . . .
C29 C 1.20024(19) 0.40482(7) 0.7099(2) 0.0445(4) Uani 1 1 d . . . . .
H29 H 1.254089 0.415462 0.654115 0.053 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
P1 O1 1.4824(10) . ?
P1 C21 1.8054(14) . ?
P1 C27 1.8047(14) . ?
P1 C1 1.8039(13) . ?
C7 C4 1.4936(18) . ?
C7 C8 1.4090(19) . ?
C7 C20 1.4098(18) . ?
C21 C26 1.390(2) . ?
C21 C22 1.3977(19) . ?
C15 C20 1.4382(19) . ?
C15 C14 1.394(2) . ?
C15 C16 1.4268(19) . ?
C4 C5 1.3939(19) . ?
C4 C3 1.3919(19) . ?
C27 C32 1.391(2) . ?
C27 C28 1.394(2) . ?
C8 C13 1.4355(18) . ?
C8 C9 1.4353(19) . ?
C13 C14 1.394(2) . ?
C13 C12 1.429(2) . ?
C20 C19 1.4305(19) . ?
C26 H26 0.9500 . ?
C26 C25 1.389(2) . ?
C14 H14 0.9500 . ?
C6 H6 0.9500 . ?
C6 C1 1.3938(19) . ?
C6 C5 1.3859(19) . ?
C1 C2 1.3937(18) . ?
C5 H5 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.360(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.3872(19) . ?
C19 H19 0.9500 . ?
C19 C18 1.364(2) . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.419(2) . ?
C32 H32 0.9500 . ?
C32 C31 1.386(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.360(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.358(2) . ?
C11 H11 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.414(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.379(2) . ?
C24 C25 1.384(2) . ?
C31 H31 0.9500 . ?
C31 C30 1.379(2) . ?
C23 H23 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.388(2) . ?
C25 H25 0.9500 . ?
C30 H30 0.9500 . ?
C30 C29 1.376(3) . ?
C18 H18 0.9500 . ?
C29 H29 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
O1 P1 C21 112.63(6) . . ?
O1 P1 C27 112.43(6) . . ?
O1 P1 C1 112.20(6) . . ?
C27 P1 C21 108.48(6) . . ?
C1 P1 C21 104.81(6) . . ?
C1 P1 C27 105.78(6) . . ?
C8 C7 C4 120.46(12) . . ?
C8 C7 C20 120.53(12) . . ?
C20 C7 C4 119.01(12) . . ?
C26 C21 P1 125.09(11) . . ?
C26 C21 C22 119.24(13) . . ?
C22 C21 P1 115.67(11) . . ?
C14 C15 C20 119.59(12) . . ?
C14 C15 C16 121.68(13) . . ?
C16 C15 C20 118.73(13) . . ?
C5 C4 C7 120.80(12) . . ?
C3 C4 C7 120.31(12) . . ?
C3 C4 C5 118.83(12) . . ?
C32 C27 P1 122.88(10) . . ?
C32 C27 C28 119.30(13) . . ?
C28 C27 P1 117.71(11) . . ?
C7 C8 C13 119.45(12) . . ?
C7 C8 C9 122.62(12) . . ?
C9 C8 C13 117.90(12) . . ?
C14 C13 C8 119.52(12) . . ?
C14 C13 C12 121.82(13) . . ?
C12 C13 C8 118.65(13) . . ?
C7 C20 C15 119.28(12) . . ?
C7 C20 C19 122.86(12) . . ?
C19 C20 C15 117.84(12) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 119.91(14) . . ?
C25 C26 H26 120.0 . . ?
C15 C14 C13 121.47(12) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C1 120.53(12) . . ?
C6 C1 P1 118.16(10) . . ?
C2 C1 P1 122.71(10) . . ?
C2 C1 C6 119.09(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.51(12) . . ?
C6 C5 H5 119.7 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.20(13) . . ?
C10 C9 H9 119.4 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.56(14) . . ?
C23 C22 H22 119.7 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.18(13) . . ?
C3 C2 H2 119.9 . . ?
C20 C19 H19 119.4 . . ?
C18 C19 C20 121.27(14) . . ?
C18 C19 H19 119.4 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.84(12) . . ?
C2 C3 H3 119.6 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.63(14) . . ?
C11 C10 H10 119.7 . . ?
C27 C32 H32 119.9 . . ?
C31 C32 C27 120.12(14) . . ?
C31 C32 H32 119.9 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.29(14) . . ?
C17 C16 H16 119.4 . . ?
C13 C12 H12 119.3 . . ?
C11 C12 C13 121.36(14) . . ?
C11 C12 H12 119.3 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.10(14) . . ?
C12 C11 H11 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.22(13) . . ?
C18 C17 H17 119.9 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.36(14) . . ?
C25 C24 H24 119.8 . . ?
C32 C31 H31 119.9 . . ?
C30 C31 C32 120.10(15) . . ?
C30 C31 H31 119.9 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.71(14) . . ?
C24 C23 H23 120.1 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.04(15) . . ?
C29 C28 H28 120.0 . . ?
C26 C25 H25 119.9 . . ?
C24 C25 C26 120.21(15) . . ?
C24 C25 H25 119.9 . . ?
C31 C30 H30 119.8 . . ?
C29 C30 C31 120.34(14) . . ?
C29 C30 H30 119.8 . . ?
C19 C18 C17 120.60(14) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.10(15) . . ?
C30 C29 H29 120.0 . . ?

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
P1 C21 C26 C25 -179.23(12) . . . . ?
P1 C21 C22 C23 179.39(11) . . . . ?
P1 C27 C32 C31 176.18(11) . . . . ?
P1 C27 C28 C29 -175.97(12) . . . . ?
P1 C1 C2 C3 176.10(11) . . . . ?
O1 P1 C21 C26 -142.06(12) . . . . ?
O1 P1 C21 C22 38.35(12) . . . . ?
O1 P1 C27 C32 -163.36(11) . . . . ?
O1 P1 C27 C28 12.63(13) . . . . ?
O1 P1 C1 C6 33.62(13) . . . . ?
O1 P1 C1 C2 -143.94(11) . . . . ?
C7 C4 C5 C6 175.71(13) . . . . ?
C7 C4 C3 C2 -175.73(13) . . . . ?
C7 C8 C13 C14 -3.84(19) . . . . ?
C7 C8 C13 C12 177.33(12) . . . . ?
C7 C8 C9 C10 -179.03(13) . . . . ?
C7 C20 C19 C18 -178.70(14) . . . . ?
C21 P1 C27 C32 71.40(13) . . . . ?
C21 P1 C27 C28 -112.60(12) . . . . ?
C21 P1 C1 C6 156.15(11) . . . . ?
C21 P1 C1 C2 -21.41(13) . . . . ?
C21 C26 C25 C24 0.1(2) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C15 C20 C19 C18 2.3(2) . . . . ?
C15 C16 C17 C18 0.8(2) . . . . ?
C4 C7 C8 C13 -175.74(12) . . . . ?
C4 C7 C8 C9 6.2(2) . . . . ?
C4 C7 C20 C15 178.56(12) . . . . ?
C4 C7 C20 C19 -0.5(2) . . . . ?
C27 P1 C21 C26 -16.95(14) . . . . ?
C27 P1 C21 C22 163.47(10) . . . . ?
C27 P1 C1 C6 -89.31(12) . . . . ?
C27 P1 C1 C2 93.13(12) . . . . ?
C27 C32 C31 C30 -0.8(2) . . . . ?
C27 C28 C29 C30 0.0(2) . . . . ?
C8 C7 C4 C5 71.62(18) . . . . ?
C8 C7 C4 C3 -111.26(15) . . . . ?
C8 C7 C20 C15 -1.3(2) . . . . ?
C8 C7 C20 C19 179.64(13) . . . . ?
C8 C13 C14 C15 0.7(2) . . . . ?
C8 C13 C12 C11 2.7(2) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C13 C8 C9 C10 2.9(2) . . . . ?
C13 C12 C11 C10 0.9(2) . . . . ?
C20 C7 C4 C5 -108.28(15) . . . . ?
C20 C7 C4 C3 68.85(17) . . . . ?
C20 C7 C8 C13 4.1(2) . . . . ?
C20 C7 C8 C9 -173.93(12) . . . . ?
C20 C15 C14 C13 2.2(2) . . . . ?
C20 C15 C16 C17 0.8(2) . . . . ?
C20 C19 C18 C17 -0.6(2) . . . . ?
C26 C21 C22 C23 -0.2(2) . . . . ?
C14 C15 C20 C7 -1.84(19) . . . . ?
C14 C15 C20 C19 177.24(13) . . . . ?
C14 C15 C16 C17 -178.71(14) . . . . ?
C14 C13 C12 C11 -176.06(14) . . . . ?
C6 C1 C2 C3 -1.4(2) . . . . ?
C1 P1 C21 C26 95.68(13) . . . . ?
C1 P1 C21 C22 -83.90(11) . . . . ?
C1 P1 C27 C32 -40.58(13) . . . . ?
C1 P1 C27 C28 135.41(12) . . . . ?
C1 C6 C5 C4 0.0(2) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C5 C4 C3 C2 1.5(2) . . . . ?
C5 C6 C1 P1 -176.21(11) . . . . ?
C5 C6 C1 C2 1.4(2) . . . . ?
C9 C8 C13 C14 174.32(12) . . . . ?
C9 C8 C13 C12 -4.51(19) . . . . ?
C9 C10 C11 C12 -2.6(2) . . . . ?
C22 C21 C26 C25 0.3(2) . . . . ?
C3 C4 C5 C6 -1.5(2) . . . . ?
C32 C27 C28 C29 0.2(2) . . . . ?
C32 C31 C30 C29 0.9(2) . . . . ?
C16 C15 C20 C7 178.60(12) . . . . ?
C16 C15 C20 C19 -2.32(19) . . . . ?
C16 C15 C14 C13 -178.30(13) . . . . ?
C16 C17 C18 C19 -0.9(2) . . . . ?
C12 C13 C14 C15 179.48(13) . . . . ?
C31 C30 C29 C28 -0.5(3) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C28 C27 C32 C31 0.2(2) . . . . ?
C25 C24 C23 C22 0.7(2) . . . . ?

_olex2_exptl_crystal_mounting_method loop
_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 1.187
_oxdiff_exptl_absorpt_empirical_full_min 0.724
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_1505
_database_code_depnum_ccdc_archive 'CCDC 2432549'
loop_
_audit_author_name
_audit_author_address
'Kosuke Katagiri'
;Konan University
Japan
;
_audit_update_record             
;
2025-03-19 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;
_audit_creation_date             2024-11-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H19 O P'
_chemical_formula_sum            'C28 H19 O P'
_chemical_formula_weight         402.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C28H19OP
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'
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                   9.88921(8)
_cell_length_b                   23.15594(18)
_cell_length_c                   8.93733(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.3493(7)
_cell_angle_gamma                90
_cell_volume                     2044.87(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8413
_cell_measurement_temperature    173
_cell_measurement_theta_max      76.6300
_cell_measurement_theta_min      4.4740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11298
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.861
_diffrn_reflns_theta_min         3.818
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     51.00  88.00   0.50    0.50    --    0.00  57.00-150.00   74
  2  ω    -25.00  24.00   0.50    0.50    --    0.00  57.00-150.00   98
  3  ω      2.00  27.00   0.50    0.50    --    0.00 -57.00  90.00   50
  4  ω    -63.00 -16.00   0.50    0.50    --    0.00 -57.00  30.00   94
  5  ω    -88.00  -5.00   0.50    0.50    --    0.00 -57.00  90.00  166
  6  ω     73.00 112.00   0.50    0.50    --  101.00 -61.00 -60.00   78
  7  ω     68.00 106.00   0.50    0.50    --  101.00  77.00  60.00   76
  8  ω     82.00 150.00   0.50    0.50    --  101.00  45.00 120.00  136
  9  ω     20.00 104.00   0.50    0.50    --  101.00 -61.00 150.00  168
 10  ω     14.00 134.00   0.50    0.50    --  101.00 -82.00 150.00  240
 11  ω     12.00 190.00   0.50    0.50    --  101.00  15.00  60.00  356
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1409411000
_diffrn_orient_matrix_UB_12      0.0239363000
_diffrn_orient_matrix_UB_13      0.0458347000
_diffrn_orient_matrix_UB_21      -0.0400115000
_diffrn_orient_matrix_UB_22      0.0019362000
_diffrn_orient_matrix_UB_23      0.1647687000
_diffrn_orient_matrix_UB_31      0.0532309000
_diffrn_orient_matrix_UB_32      -0.0620398000
_diffrn_orient_matrix_UB_33      0.0229901000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3959
_reflns_number_total             4195
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0052(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.048
_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)+(0.0643P)²+0.5579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1119
_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:
 C15(H15), C18(H18), C24(H24), C28(H28), C12(H12), C10(H10), C5(H5), C14(H14),
 C8(H8), C22(H22), C27(H27), C25(H25), C19(H19), C26(H26), C7(H7), C6(H6),
 C20(H20), C21(H21), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
P1 P 0.22152(3) 0.35198(2) 0.69281(4) 0.02182(13) Uani 1 1 d . . . . .
O1 O 0.18121(10) 0.31992(4) 0.82696(11) 0.0307(2) Uani 1 1 d . . . . .
C3 C 0.36307(12) 0.52116(5) 0.83826(14) 0.0219(3) Uani 1 1 d . . . . .
C4 C 0.50109(13) 0.53210(6) 0.81171(14) 0.0233(3) Uani 1 1 d . . . . .
C2 C 0.30139(13) 0.47024(6) 0.77621(14) 0.0231(3) Uani 1 1 d . . . . .
C11 C 0.35681(13) 0.60573(5) 1.00298(15) 0.0246(3) Uani 1 1 d . . . . .
C16 C 0.28875(13) 0.55775(5) 0.93123(14) 0.0224(3) Uani 1 1 d . . . . .
C9 C 0.56658(13) 0.58027(6) 0.88496(14) 0.0248(3) Uani 1 1 d . . . . .
C17 C 0.09775(13) 0.35126(5) 0.53974(15) 0.0239(3) Uani 1 1 d . . . . .
C15 C 0.14863(13) 0.54923(6) 0.95653(15) 0.0264(3) Uani 1 1 d . . . . .
H15 H 0.102440 0.517253 0.911699 0.032 Uiso 1 1 calc R U . . .
C18 C 0.00274(14) 0.39558(6) 0.52147(16) 0.0281(3) Uani 1 1 d . . . . .
H18 H 0.004898 0.427547 0.588144 0.034 Uiso 1 1 calc R U . . .
C1 C 0.25551(13) 0.42536(6) 0.72838(15) 0.0252(3) Uani 1 1 d . . . . .
C24 C 0.43647(14) 0.27624(6) 0.67737(16) 0.0282(3) Uani 1 1 d . . . . .
H24 H 0.392160 0.254489 0.751017 0.034 Uiso 1 1 calc R U . . .
C28 C 0.44230(14) 0.35785(6) 0.50975(16) 0.0286(3) Uani 1 1 d . . . . .
H28 H 0.401271 0.391729 0.468716 0.034 Uiso 1 1 calc R U . . .
C23 C 0.37793(13) 0.32663(6) 0.61972(15) 0.0238(3) Uani 1 1 d . . . . .
C12 C 0.28112(16) 0.64264(6) 1.09649(17) 0.0309(3) Uani 1 1 d . . . . .
H12 H 0.325434 0.674010 1.146397 0.037 Uiso 1 1 calc R U . . .
C10 C 0.49326(14) 0.61532(6) 0.97930(15) 0.0263(3) Uani 1 1 d . . . . .
H10 H 0.537789 0.646699 1.028912 0.032 Uiso 1 1 calc R U . . .
C5 C 0.57868(14) 0.49653(6) 0.71700(15) 0.0287(3) Uani 1 1 d . . . . .
H5 H 0.537360 0.464310 0.667782 0.034 Uiso 1 1 calc R U . . .
C14 C 0.08016(14) 0.58653(6) 1.04447(17) 0.0312(3) Uani 1 1 d . . . . .
H14 H -0.013607 0.580685 1.058182 0.037 Uiso 1 1 calc R U . . .
C8 C 0.70640(14) 0.59084(7) 0.86048(16) 0.0312(3) Uani 1 1 d . . . . .
H8 H 0.750706 0.622669 0.908288 0.037 Uiso 1 1 calc R U . . .
C22 C 0.09292(14) 0.30414(6) 0.44323(17) 0.0306(3) Uani 1 1 d . . . . .
H22 H 0.156483 0.273626 0.456519 0.037 Uiso 1 1 calc R U . . .
C27 C 0.56637(15) 0.33939(7) 0.46024(17) 0.0329(3) Uani 1 1 d . . . . .
H27 H 0.610734 0.360830 0.386042 0.039 Uiso 1 1 calc R U . . .
C25 C 0.56062(15) 0.25796(6) 0.62615(17) 0.0325(3) Uani 1 1 d . . . . .
H25 H 0.600935 0.223545 0.664918 0.039 Uiso 1 1 calc R U . . .
C19 C -0.09481(14) 0.39277(7) 0.40562(17) 0.0324(3) Uani 1 1 d . . . . .
H19 H -0.159374 0.422931 0.392766 0.039 Uiso 1 1 calc R U . . .
C26 C 0.62540(14) 0.28958(7) 0.51934(17) 0.0336(3) Uani 1 1 d . . . . .
H26 H 0.710721 0.277178 0.486226 0.040 Uiso 1 1 calc R U . . .
C7 C 0.77658(14) 0.55579(7) 0.76947(17) 0.0355(3) Uani 1 1 d . . . . .
H7 H 0.869605 0.563107 0.754679 0.043 Uiso 1 1 calc R U . . .
C6 C 0.71164(15) 0.50845(7) 0.69665(17) 0.0352(3) Uani 1 1 d . . . . .
H6 H 0.761608 0.484569 0.632460 0.042 Uiso 1 1 calc R U . . .
C20 C -0.09822(14) 0.34617(7) 0.30888(17) 0.0320(3) Uani 1 1 d . . . . .
H20 H -0.164822 0.344584 0.229316 0.038 Uiso 1 1 calc R U . . .
C21 C -0.00507(15) 0.30173(7) 0.32721(17) 0.0343(3) Uani 1 1 d . . . . .
H21 H -0.008154 0.269711 0.260705 0.041 Uiso 1 1 calc R U . . .
C13 C 0.14723(16) 0.63384(7) 1.11553(17) 0.0342(3) Uani 1 1 d . . . . .
H13 H 0.098424 0.659410 1.176536 0.041 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
P1 O1 1.4788(10) . ?
P1 C17 1.7980(14) . ?
P1 C1 1.7585(14) . ?
P1 C23 1.8019(13) . ?
C3 C4 1.4177(17) . ?
C3 C2 1.4290(18) . ?
C3 C16 1.4138(18) . ?
C4 C9 1.4343(18) . ?
C4 C5 1.4273(19) . ?
C2 C1 1.2053(19) . ?
C11 C16 1.4363(17) . ?
C11 C12 1.4285(19) . ?
C11 C10 1.3922(19) . ?
C16 C15 1.4268(18) . ?
C9 C10 1.3948(19) . ?
C9 C8 1.4299(18) . ?
C17 C18 1.3963(19) . ?
C17 C22 1.3905(19) . ?
C15 H15 0.9500 . ?
C15 C14 1.3660(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.3921(19) . ?
C24 C25 1.394(2) . ?
C28 H28 0.9500 . ?
C28 C23 1.3946(19) . ?
C28 C27 1.3887(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.357(2) . ?
C10 H10 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.363(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.417(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.359(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.391(2) . ?
C27 H27 0.9500 . ?
C27 C26 1.387(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.381(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(2) . ?
C26 H26 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.415(2) . ?
C6 H6 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.386(2) . ?
C21 H21 0.9500 . ?
C13 H13 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
O1 P1 C17 114.49(6) . . ?
O1 P1 C1 113.23(6) . . ?
O1 P1 C23 113.22(6) . . ?
C17 P1 C23 106.79(6) . . ?
C1 P1 C17 105.41(6) . . ?
C1 P1 C23 102.69(6) . . ?
C4 C3 C2 118.76(12) . . ?
C16 C3 C4 121.23(12) . . ?
C16 C3 C2 119.92(11) . . ?
C3 C4 C9 118.85(12) . . ?
C3 C4 C5 122.74(12) . . ?
C5 C4 C9 118.41(12) . . ?
C1 C2 C3 175.99(14) . . ?
C12 C11 C16 118.48(12) . . ?
C10 C11 C16 119.66(12) . . ?
C10 C11 C12 121.86(12) . . ?
C3 C16 C11 118.73(12) . . ?
C3 C16 C15 122.81(12) . . ?
C15 C16 C11 118.46(12) . . ?
C10 C9 C4 119.48(12) . . ?
C10 C9 C8 121.52(13) . . ?
C8 C9 C4 118.99(13) . . ?
C18 C17 P1 121.06(10) . . ?
C22 C17 P1 118.96(10) . . ?
C22 C17 C18 119.89(13) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 C16 120.75(12) . . ?
C14 C15 H15 119.6 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.79(13) . . ?
C19 C18 H18 120.1 . . ?
C2 C1 P1 164.50(12) . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.45(13) . . ?
C25 C24 H24 120.3 . . ?
C23 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C23 119.99(13) . . ?
C24 C23 P1 119.28(10) . . ?
C24 C23 C28 120.03(12) . . ?
C28 C23 P1 120.66(10) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.38(13) . . ?
C13 C12 H12 119.3 . . ?
C11 C10 C9 122.02(12) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.48(14) . . ?
C6 C5 H5 119.8 . . ?
C15 C14 H14 119.6 . . ?
C15 C14 C13 120.84(13) . . ?
C13 C14 H14 119.6 . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.66(14) . . ?
C7 C8 H8 119.7 . . ?
C17 C22 H22 120.0 . . ?
C17 C22 C21 119.94(13) . . ?
C21 C22 H22 120.0 . . ?
C28 C27 H27 120.1 . . ?
C26 C27 C28 119.87(14) . . ?
C26 C27 H27 120.1 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.38(13) . . ?
C26 C25 H25 119.8 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.11(13) . . ?
C20 C19 H19 119.9 . . ?
C27 C26 H26 119.9 . . ?
C25 C26 C27 120.27(13) . . ?
C25 C26 H26 119.9 . . ?
C8 C7 H7 119.9 . . ?
C8 C7 C6 120.29(13) . . ?
C6 C7 H7 119.9 . . ?
C5 C6 C7 121.17(14) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.43(13) . . ?
C21 C20 H20 119.8 . . ?
C22 C21 H21 120.1 . . ?
C20 C21 C22 119.83(13) . . ?
C20 C21 H21 120.1 . . ?
C12 C13 C14 120.06(13) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?

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
P1 C17 C18 C19 -177.55(10) . . . . ?
P1 C17 C22 C21 177.74(11) . . . . ?
O1 P1 C17 C18 93.49(12) . . . . ?
O1 P1 C17 C22 -83.13(12) . . . . ?
O1 P1 C1 C2 59.5(5) . . . . ?
O1 P1 C23 C24 8.89(13) . . . . ?
O1 P1 C23 C28 -169.21(11) . . . . ?
C3 C4 C9 C10 -0.46(18) . . . . ?
C3 C4 C9 C8 178.93(11) . . . . ?
C3 C4 C5 C6 -179.13(13) . . . . ?
C3 C16 C15 C14 -178.42(13) . . . . ?
C4 C3 C16 C11 -1.91(18) . . . . ?
C4 C3 C16 C15 177.84(12) . . . . ?
C4 C9 C10 C11 -1.2(2) . . . . ?
C4 C9 C8 C7 -0.1(2) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C2 C3 C4 C9 -174.37(11) . . . . ?
C2 C3 C4 C5 4.46(19) . . . . ?
C2 C3 C16 C11 174.43(11) . . . . ?
C2 C3 C16 C15 -5.82(19) . . . . ?
C11 C16 C15 C14 1.33(19) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
C16 C3 C4 C9 2.00(18) . . . . ?
C16 C3 C4 C5 -179.16(12) . . . . ?
C16 C11 C12 C13 -1.4(2) . . . . ?
C16 C11 C10 C9 1.3(2) . . . . ?
C16 C15 C14 C13 -1.5(2) . . . . ?
C9 C4 C5 C6 -0.3(2) . . . . ?
C9 C8 C7 C6 0.5(2) . . . . ?
C17 P1 C1 C2 -174.6(4) . . . . ?
C17 P1 C23 C24 -118.03(11) . . . . ?
C17 P1 C23 C28 63.87(12) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C17 C22 C21 C20 -0.5(2) . . . . ?
C15 C14 C13 C12 0.1(2) . . . . ?
C18 C17 C22 C21 1.1(2) . . . . ?
C18 C19 C20 C21 0.4(2) . . . . ?
C1 P1 C17 C18 -31.61(13) . . . . ?
C1 P1 C17 C22 151.77(11) . . . . ?
C1 P1 C23 C24 131.34(11) . . . . ?
C1 P1 C23 C28 -46.76(12) . . . . ?
C24 C25 C26 C27 -1.0(2) . . . . ?
C28 C27 C26 C25 0.7(2) . . . . ?
C23 P1 C17 C18 -140.35(11) . . . . ?
C23 P1 C17 C22 43.03(13) . . . . ?
C23 P1 C1 C2 -63.0(5) . . . . ?
C23 C24 C25 C26 0.2(2) . . . . ?
C23 C28 C27 C26 0.6(2) . . . . ?
C12 C11 C16 C3 179.85(12) . . . . ?
C12 C11 C16 C15 0.08(18) . . . . ?
C12 C11 C10 C9 -178.28(13) . . . . ?
C10 C11 C16 C3 0.26(19) . . . . ?
C10 C11 C16 C15 -179.50(12) . . . . ?
C10 C11 C12 C13 178.15(14) . . . . ?
C10 C9 C8 C7 179.24(13) . . . . ?
C5 C4 C9 C10 -179.34(12) . . . . ?
C5 C4 C9 C8 0.04(18) . . . . ?
C8 C9 C10 C11 179.45(12) . . . . ?
C8 C7 C6 C5 -0.7(2) . . . . ?
C22 C17 C18 C19 -1.0(2) . . . . ?
C27 C28 C23 P1 176.58(11) . . . . ?
C27 C28 C23 C24 -1.5(2) . . . . ?
C25 C24 C23 P1 -177.00(10) . . . . ?
C25 C24 C23 C28 1.1(2) . . . . ?
C19 C20 C21 C22 -0.3(2) . . . . ?

_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 1.208
_oxdiff_exptl_absorpt_empirical_full_min 0.851
####################################################################### 
# 
# 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_1506
_database_code_depnum_ccdc_archive 'CCDC 2432553'
loop_
_audit_author_name
_audit_author_address
'Kosuke Katagiri'
;Konan University
Japan
;
_audit_update_record             
;
2025-03-19 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;
_audit_creation_date             2024-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H19 O P'
_chemical_formula_sum            'C30 H19 O P'
_chemical_formula_weight         426.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H19OP
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'
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                   9.90452(11)
_cell_length_b                   19.8613(2)
_cell_length_c                   11.16039(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.3245(10)
_cell_angle_gamma                90
_cell_volume                     2159.88(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8683
_cell_measurement_temperature    173
_cell_measurement_theta_max      76.7140
_cell_measurement_theta_min      4.4570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.277
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12031
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.128
_diffrn_reflns_theta_min         4.452
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  26.00   0.50    0.50    --    0.00 -37.00 -30.00  154
  2  ω    -14.00  12.00   0.50    0.50    --    0.00  37.00-150.00   52
  3  ω     13.00  88.00   0.50    0.50    --    0.00  19.00 -30.00  150
  4  ω    -20.00   5.00   0.50    0.50    --    0.00  19.00 -30.00   50
  5  ω     34.00  59.00   0.50    0.50    --    0.00  37.00-150.00   50
  6  ω     12.00 128.00   0.50    0.50    --  101.00 -61.00-180.00  232
  7  ω     17.00 114.00   0.50    0.50    --  101.00 -45.00   0.00  194
  8  ω     13.00 130.00   0.50    0.50    --  101.00 -30.00   0.00  234
  9  ω    156.00 190.00   0.50    0.50    --  101.00  45.00  90.00   68
 10  ω    109.00 134.00   0.50    0.50    --  101.00  45.00  90.00   50
 11  ω    108.00 183.00   0.50    0.50    --  101.00  45.00 -60.00  150
 12  ω     93.00 119.00   0.50    0.50    --  101.00 -77.00 150.00   52
 13  ω    151.00 176.00   0.50    0.50    --  101.00  48.00 -37.00   50
 14  ω     16.00  44.00   0.50    0.50    --  101.00 -77.00 150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0895154000
_diffrn_orient_matrix_UB_12      0.0163680000
_diffrn_orient_matrix_UB_13      0.1242067000
_diffrn_orient_matrix_UB_21      0.0949498000
_diffrn_orient_matrix_UB_22      0.0430736000
_diffrn_orient_matrix_UB_23      -0.0641837000
_diffrn_orient_matrix_UB_31      -0.0892510000
_diffrn_orient_matrix_UB_32      0.0624187000
_diffrn_orient_matrix_UB_33      0.0116417000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4109
_reflns_number_total             4410
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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         0.202
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.6881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1083
_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:
 C5(H5), C4(H4), C15(H15), C7(H7), C14(H14), C20(H20), C10(H10), C8(H8),
 C26(H26), C12(H12), C11(H11), C24(H24), C22(H22), C30(H30), C23(H23), C21(H21),
  C27(H27), C29(H29), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
P1 P 0.45876(3) 0.38902(2) 0.15107(3) 0.02766(11) Uani 1 1 d . . . . .
O1 O 0.39979(11) 0.45015(5) 0.08581(9) 0.0359(2) Uani 1 1 d . . . . .
C17 C 0.95755(13) 0.44008(6) 0.62256(11) 0.0239(3) Uani 1 1 d . . . . .
C3 C 0.73071(14) 0.43697(6) 0.49520(11) 0.0264(3) Uani 1 1 d . . . . .
C16 C 0.87249(13) 0.42307(6) 0.51015(11) 0.0240(3) Uani 1 1 d . . . . .
C18 C 1.10115(13) 0.42660(6) 0.64104(12) 0.0256(3) Uani 1 1 d . . . . .
C9 C 1.18637(14) 0.44432(7) 0.75330(12) 0.0299(3) Uani 1 1 d . . . . .
C6 C 0.90003(14) 0.47088(7) 0.71716(11) 0.0278(3) Uani 1 1 d . . . . .
C2 C 0.64068(14) 0.41979(7) 0.38427(12) 0.0293(3) Uani 1 1 d . . . . .
C5 C 0.75892(14) 0.48340(7) 0.69866(12) 0.0314(3) Uani 1 1 d . . . . .
H5 H 0.7198 0.5035 0.7617 0.038 Uiso 1 1 calc R . . . .
C13 C 1.15944(15) 0.39568(7) 0.54784(13) 0.0295(3) Uani 1 1 d . . . . .
C4 C 0.67588(14) 0.46679(7) 0.58962(12) 0.0298(3) Uani 1 1 d . . . . .
H4 H 0.5802 0.4757 0.5785 0.036 Uiso 1 1 calc R . . . .
C25 C 0.32997(14) 0.33171(7) 0.18481(13) 0.0328(3) Uani 1 1 d . . . . .
C1 C 0.56339(15) 0.40476(7) 0.29197(13) 0.0324(3) Uani 1 1 d . . . . .
C19 C 0.57054(14) 0.34323(7) 0.06880(12) 0.0306(3) Uani 1 1 d . . . . .
C15 C 0.93478(15) 0.39274(7) 0.41684(12) 0.0301(3) Uani 1 1 d . . . . .
H15 H 0.8793 0.3814 0.3410 0.036 Uiso 1 1 calc R . . . .
C7 C 0.98920(15) 0.48885(8) 0.82872(12) 0.0356(3) Uani 1 1 d . . . . .
H7 H 0.9517 0.5099 0.8918 0.043 Uiso 1 1 calc R . . . .
C14 C 1.07103(16) 0.38004(7) 0.43488(13) 0.0330(3) Uani 1 1 d . . . . .
H14 H 1.1092 0.3602 0.3710 0.040 Uiso 1 1 calc R . . . .
C20 C 0.62832(15) 0.37753(8) -0.01818(14) 0.0373(3) Uani 1 1 d . . . . .
H20 H 0.6082 0.4238 -0.0337 0.045 Uiso 1 1 calc R . . . .
C10 C 1.32647(15) 0.42986(8) 0.77029(15) 0.0376(3) Uani 1 1 d . . . . .
H10 H 1.3843 0.4419 0.8446 0.045 Uiso 1 1 calc R . . . .
C8 C 1.12513(16) 0.47642(8) 0.84566(13) 0.0367(3) Uani 1 1 d . . . . .
H8 H 1.1815 0.4892 0.9203 0.044 Uiso 1 1 calc R . . . .
C26 C 0.35441(17) 0.28519(8) 0.27986(15) 0.0406(3) Uani 1 1 d . . . . .
H26 H 0.4421 0.2834 0.3308 0.049 Uiso 1 1 calc R . . . .
C12 C 1.30012(16) 0.38186(8) 0.56946(15) 0.0378(3) Uani 1 1 d . . . . .
H12 H 1.3403 0.3610 0.5077 0.045 Uiso 1 1 calc R . . . .
C11 C 1.38170(15) 0.39821(8) 0.68006(16) 0.0403(4) Uani 1 1 d . . . . .
H11 H 1.4767 0.3875 0.6939 0.048 Uiso 1 1 calc R . . . .
C24 C 0.60263(17) 0.27566(8) 0.09236(16) 0.0426(4) Uani 1 1 d . . . . .
H24 H 0.5637 0.2520 0.1519 0.051 Uiso 1 1 calc R . . . .
C22 C 0.74640(17) 0.27676(9) -0.05918(16) 0.0469(4) Uani 1 1 d . . . . .
H22 H 0.8055 0.2539 -0.1039 0.056 Uiso 1 1 calc R . . . .
C30 C 0.20057(17) 0.33416(10) 0.11142(16) 0.0467(4) Uani 1 1 d . . . . .
H30 H 0.1819 0.3658 0.0467 0.056 Uiso 1 1 calc R . . . .
C23 C 0.69153(18) 0.24304(8) 0.02869(18) 0.0487(4) Uani 1 1 d . . . . .
H23 H 0.7147 0.1972 0.0458 0.058 Uiso 1 1 calc R . . . .
C21 C 0.71554(17) 0.34391(10) -0.08232(16) 0.0466(4) Uani 1 1 d . . . . .
H21 H 0.7542 0.3672 -0.1424 0.056 Uiso 1 1 calc R . . . .
C27 C 0.2521(2) 0.24176(9) 0.3005(2) 0.0563(5) Uani 1 1 d . . . . .
H27 H 0.2697 0.2103 0.3655 0.068 Uiso 1 1 calc R . . . .
C29 C 0.09862(19) 0.28985(12) 0.1336(2) 0.0656(6) Uani 1 1 d . . . . .
H29 H 0.0102 0.2914 0.0838 0.079 Uiso 1 1 calc R . . . .
C28 C 0.1250(2) 0.24395(11) 0.2271(2) 0.0666(7) Uani 1 1 d . . . . .
H28 H 0.0551 0.2137 0.2410 0.080 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
P1 O1 1.4810(10) . ?
P1 C25 1.7992(15) . ?
P1 C1 1.7494(15) . ?
P1 C19 1.8056(14) . ?
C17 C16 1.4209(17) . ?
C17 C18 1.4255(18) . ?
C17 C6 1.4246(17) . ?
C3 C16 1.4114(18) . ?
C3 C2 1.4312(18) . ?
C3 C4 1.4005(19) . ?
C16 C15 1.4347(18) . ?
C18 C9 1.4237(18) . ?
C18 C13 1.4170(19) . ?
C9 C10 1.396(2) . ?
C9 C8 1.436(2) . ?
C6 C5 1.3979(19) . ?
C6 C7 1.4364(18) . ?
C2 C1 1.206(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.3811(19) . ?
C13 C14 1.434(2) . ?
C13 C12 1.398(2) . ?
C4 H4 0.9500 . ?
C25 C26 1.395(2) . ?
C25 C30 1.393(2) . ?
C19 C20 1.390(2) . ?
C19 C24 1.393(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.352(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.348(2) . ?
C14 H14 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.388(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(2) . ?
C8 H8 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.381(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C24 H24 0.9500 . ?
C24 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(3) . ?
C22 C21 1.382(3) . ?
C30 H30 0.9500 . ?
C30 C29 1.395(3) . ?
C23 H23 0.9500 . ?
C21 H21 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.374(3) . ?
C29 H29 0.9500 . ?
C29 C28 1.375(4) . ?
C28 H28 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
O1 P1 C25 112.94(7) . . ?
O1 P1 C1 114.42(6) . . ?
O1 P1 C19 112.75(6) . . ?
C25 P1 C19 108.07(6) . . ?
C1 P1 C25 104.65(7) . . ?
C1 P1 C19 103.22(6) . . ?
C16 C17 C18 120.10(12) . . ?
C16 C17 C6 120.25(12) . . ?
C6 C17 C18 119.64(12) . . ?
C16 C3 C2 120.53(12) . . ?
C4 C3 C16 120.37(12) . . ?
C4 C3 C2 119.09(12) . . ?
C17 C16 C15 118.46(12) . . ?
C3 C16 C17 118.55(11) . . ?
C3 C16 C15 122.99(12) . . ?
C9 C18 C17 119.98(12) . . ?
C13 C18 C17 120.16(12) . . ?
C13 C18 C9 119.86(12) . . ?
C18 C9 C8 118.79(12) . . ?
C10 C9 C18 119.12(13) . . ?
C10 C9 C8 122.10(13) . . ?
C17 C6 C7 118.92(12) . . ?
C5 C6 C17 119.27(12) . . ?
C5 C6 C7 121.81(12) . . ?
C1 C2 C3 178.88(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.63(12) . . ?
C4 C5 H5 119.7 . . ?
C18 C13 C14 118.31(13) . . ?
C12 C13 C18 118.88(13) . . ?
C12 C13 C14 122.81(13) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.93(12) . . ?
C5 C4 H4 119.5 . . ?
C26 C25 P1 123.05(12) . . ?
C30 C25 P1 117.84(13) . . ?
C30 C25 C26 119.11(15) . . ?
C2 C1 P1 174.50(14) . . ?
C20 C19 P1 118.35(11) . . ?
C20 C19 C24 119.69(14) . . ?
C24 C19 P1 121.95(12) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 C16 121.19(13) . . ?
C14 C15 H15 119.4 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.30(13) . . ?
C8 C7 H7 119.3 . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.77(12) . . ?
C15 C14 H14 119.1 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.77(15) . . ?
C21 C20 H20 120.1 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.58(14) . . ?
C11 C10 H10 119.7 . . ?
C9 C8 H8 119.3 . . ?
C7 C8 C9 121.36(13) . . ?
C7 C8 H8 119.3 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.53(17) . . ?
C27 C26 H26 119.7 . . ?
C13 C12 H12 119.6 . . ?
C11 C12 C13 120.74(14) . . ?
C11 C12 H12 119.6 . . ?
C10 C11 C12 120.79(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C19 C24 H24 120.1 . . ?
C23 C24 C19 119.84(16) . . ?
C23 C24 H24 120.1 . . ?
C23 C22 H22 120.0 . . ?
C23 C22 C21 120.00(15) . . ?
C21 C22 H22 120.0 . . ?
C25 C30 H30 120.2 . . ?
C25 C30 C29 119.52(19) . . ?
C29 C30 H30 120.2 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.35(16) . . ?
C22 C23 H23 119.8 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.34(16) . . ?
C22 C21 H21 119.8 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C30 C29 H29 119.7 . . ?
C28 C29 C30 120.55(19) . . ?
C28 C29 H29 119.7 . . ?
C27 C28 C29 120.13(18) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?

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
P1 C25 C26 C27 -179.08(12) . . . . ?
P1 C25 C30 C29 179.08(13) . . . . ?
P1 C19 C20 C21 179.50(12) . . . . ?
P1 C19 C24 C23 -178.52(13) . . . . ?
O1 P1 C25 C26 -155.77(12) . . . . ?
O1 P1 C25 C30 24.65(14) . . . . ?
O1 P1 C19 C20 21.87(13) . . . . ?
O1 P1 C19 C24 -159.80(12) . . . . ?
C17 C16 C15 C14 0.43(19) . . . . ?
C17 C18 C9 C10 179.12(12) . . . . ?
C17 C18 C9 C8 -0.73(19) . . . . ?
C17 C18 C13 C14 1.41(19) . . . . ?
C17 C18 C13 C12 -178.74(12) . . . . ?
C17 C6 C5 C4 -0.6(2) . . . . ?
C17 C6 C7 C8 -0.8(2) . . . . ?
C3 C16 C15 C14 -179.80(13) . . . . ?
C16 C17 C18 C9 179.36(11) . . . . ?
C16 C17 C18 C13 -0.54(18) . . . . ?
C16 C17 C6 C5 0.77(19) . . . . ?
C16 C17 C6 C7 -178.62(12) . . . . ?
C16 C3 C4 C5 0.3(2) . . . . ?
C16 C15 C14 C13 0.5(2) . . . . ?
C18 C17 C16 C3 179.83(11) . . . . ?
C18 C17 C16 C15 -0.39(18) . . . . ?
C18 C17 C6 C5 -179.46(12) . . . . ?
C18 C17 C6 C7 1.15(19) . . . . ?
C18 C9 C10 C11 -0.6(2) . . . . ?
C18 C9 C8 C7 1.2(2) . . . . ?
C18 C13 C14 C15 -1.4(2) . . . . ?
C18 C13 C12 C11 -0.2(2) . . . . ?
C9 C18 C13 C14 -178.49(12) . . . . ?
C9 C18 C13 C12 1.36(19) . . . . ?
C9 C10 C11 C12 1.9(2) . . . . ?
C6 C17 C16 C3 -0.41(18) . . . . ?
C6 C17 C16 C15 179.37(12) . . . . ?
C6 C17 C18 C9 -0.41(19) . . . . ?
C6 C17 C18 C13 179.69(12) . . . . ?
C6 C5 C4 C3 0.1(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C2 C3 C16 C17 -179.04(11) . . . . ?
C2 C3 C16 C15 1.19(19) . . . . ?
C2 C3 C4 C5 179.21(13) . . . . ?
C5 C6 C7 C8 179.87(14) . . . . ?
C13 C18 C9 C10 -0.98(19) . . . . ?
C13 C18 C9 C8 179.17(12) . . . . ?
C13 C12 C11 C10 -1.5(2) . . . . ?
C4 C3 C16 C17 -0.11(18) . . . . ?
C4 C3 C16 C15 -179.88(12) . . . . ?
C25 P1 C19 C20 147.40(11) . . . . ?
C25 P1 C19 C24 -34.27(14) . . . . ?
C25 C26 C27 C28 0.1(2) . . . . ?
C25 C30 C29 C28 0.0(3) . . . . ?
C1 P1 C25 C26 -30.70(14) . . . . ?
C1 P1 C25 C30 149.72(12) . . . . ?
C1 P1 C19 C20 -102.12(12) . . . . ?
C1 P1 C19 C24 76.21(14) . . . . ?
C19 P1 C25 C26 78.81(13) . . . . ?
C19 P1 C25 C30 -100.78(12) . . . . ?
C19 C20 C21 C22 -0.7(2) . . . . ?
C19 C24 C23 C22 -1.1(3) . . . . ?
C7 C6 C5 C4 178.75(13) . . . . ?
C14 C13 C12 C11 179.69(13) . . . . ?
C20 C19 C24 C23 -0.2(2) . . . . ?
C10 C9 C8 C7 -178.69(15) . . . . ?
C8 C9 C10 C11 179.21(14) . . . . ?
C26 C25 C30 C29 -0.5(2) . . . . ?
C26 C27 C28 C29 -0.6(3) . . . . ?
C12 C13 C14 C15 178.76(13) . . . . ?
C24 C19 C20 C21 1.1(2) . . . . ?
C30 C25 C26 C27 0.5(2) . . . . ?
C30 C29 C28 C27 0.6(3) . . . . ?
C23 C22 C21 C20 -0.6(3) . . . . ?
C21 C22 C23 C24 1.5(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method loop
_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 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.723
####################################################################### 
# 
# 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_1457
_database_code_depnum_ccdc_archive 'CCDC 2432552'
loop_
_audit_author_name
_audit_author_address
'Kosuke Katagiri'
;Konan University
Japan
;
_audit_update_record             
;
2025-03-19 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;
_audit_creation_date             2023-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H19 O P'
_chemical_formula_sum            'C30 H19 O P'
_chemical_formula_weight         426.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H19OP
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'
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                   8.70743(11)
_cell_length_b                   11.37805(14)
_cell_length_c                   21.6228(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.7870(11)
_cell_angle_gamma                90
_cell_volume                     2131.33(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6335
_cell_measurement_temperature    173
_cell_measurement_theta_max      76.8980
_cell_measurement_theta_min      4.3800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.294
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11624
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.291
_diffrn_reflns_theta_min         4.110
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00   6.00   0.50    0.71    --    0.00  68.00  94.00   54
  2  ω    -88.00 -16.00   0.50    0.71    --    0.00 -57.00-120.00  144
  3  ω    -16.00  88.00   0.50    0.71    --    0.00  57.00 -90.00  208
  4  ω     23.00  48.00   0.50    0.71    --    0.00  68.00  94.00   50
  5  ω     85.00 133.00   0.50    2.84    --  101.00  61.00-150.00   96
  6  ω    139.00 165.00   0.50    2.84    --  101.00  61.00-150.00   52
  7  ω     37.00 113.00   0.50    2.84    --  101.00 -61.00-120.00  152
  8  ω     16.00 127.00   0.50    2.84    --  101.00 -82.00  90.00  222
  9  ω     12.00 128.00   0.50    2.84    --  101.00 -61.00  90.00  232
 10  ω     12.00 166.00   0.50    2.84    --  101.00  15.00  60.00  308
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0358313000
_diffrn_orient_matrix_UB_12      -0.0916055000
_diffrn_orient_matrix_UB_13      0.0490505000
_diffrn_orient_matrix_UB_21      -0.1112240000
_diffrn_orient_matrix_UB_22      0.0872368000
_diffrn_orient_matrix_UB_23      0.0267758000
_diffrn_orient_matrix_UB_31      -0.1340239000
_diffrn_orient_matrix_UB_32      -0.0481899000
_diffrn_orient_matrix_UB_33      -0.0448072000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3841
_reflns_number_total             4366
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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         0.293
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.109
_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)+(0.0675P)²+1.0130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1377
_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:
 C24(H24), C20(H20), C5(H5), C30(H30), C4(H4), C26(H26), C7(H7), C15(H15),
 C8(H8), C22(H22), C21(H21), C12(H12), C27(H27), C14(H14), C23(H23), C10(H10),
 C11(H11), C28(H28), C29(H29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
P1 P 0.40523(5) 0.53110(4) 0.23632(2) 0.02350(14) Uani 1 1 d . . . . .
O1 O 0.35058(16) 0.65308(11) 0.22385(6) 0.0301(3) Uani 1 1 d . . . . .
C17 C 0.8276(2) 0.40752(16) 0.50136(8) 0.0258(4) Uani 1 1 d . . . . .
C16 C 0.7509(2) 0.40804(16) 0.44010(8) 0.0281(4) Uani 1 1 d . . . . .
C18 C 0.9345(2) 0.31664(15) 0.52014(8) 0.0266(4) Uani 1 1 d . . . . .
C25 C 0.5114(2) 0.47684(15) 0.17500(8) 0.0252(4) Uani 1 1 d . . . . .
C19 C 0.2493(2) 0.42999(16) 0.24444(8) 0.0255(4) Uani 1 1 d . . . . .
C6 C 0.8011(2) 0.49942(16) 0.54359(8) 0.0267(4) Uani 1 1 d . . . . .
C24 C 0.1011(2) 0.46813(16) 0.22474(9) 0.0297(4) Uani 1 1 d . . . . .
H24 H 0.0860 0.5435 0.2063 0.036 Uiso 1 1 calc R . . . .
C20 C 0.2710(2) 0.31824(17) 0.27104(9) 0.0309(4) Uani 1 1 d . . . . .
H20 H 0.3720 0.2912 0.2847 0.037 Uiso 1 1 calc R . . . .
C5 C 0.6984(2) 0.59010(17) 0.52381(9) 0.0313(4) Uani 1 1 d . . . . .
H5 H 0.6782 0.6509 0.5520 0.038 Uiso 1 1 calc R . . . .
C2 C 0.5810(2) 0.50933(18) 0.35932(9) 0.0314(4) Uani 1 1 d . . . . .
C30 C 0.5271(2) 0.55232(18) 0.12511(9) 0.0342(4) Uani 1 1 d . . . . .
H30 H 0.4863 0.6298 0.1253 0.041 Uiso 1 1 calc R . . . .
C3 C 0.6525(2) 0.50286(18) 0.42187(8) 0.0296(4) Uani 1 1 d . . . . .
C1 C 0.5223(2) 0.51597(17) 0.30652(9) 0.0317(4) Uani 1 1 d . . . . .
C13 C 0.9635(2) 0.22511(17) 0.47794(9) 0.0309(4) Uani 1 1 d . . . . .
C4 C 0.6263(2) 0.59233(18) 0.46408(9) 0.0324(4) Uani 1 1 d . . . . .
H4 H 0.5584 0.6551 0.4514 0.039 Uiso 1 1 calc R . . . .
C26 C 0.5714(2) 0.36317(17) 0.17413(9) 0.0318(4) Uani 1 1 d . . . . .
H26 H 0.5611 0.3113 0.2079 0.038 Uiso 1 1 calc R . . . .
C7 C 0.8821(2) 0.49744(18) 0.60446(8) 0.0304(4) Uani 1 1 d . . . . .
H7 H 0.8635 0.5576 0.6332 0.037 Uiso 1 1 calc R . . . .
C9 C 1.0154(2) 0.31793(17) 0.58044(8) 0.0292(4) Uani 1 1 d . . . . .
C15 C 0.7789(2) 0.31268(18) 0.39914(9) 0.0328(4) Uani 1 1 d . . . . .
H15 H 0.7261 0.3107 0.3585 0.039 Uiso 1 1 calc R . . . .
C8 C 0.9849(2) 0.41129(18) 0.62187(8) 0.0320(4) Uani 1 1 d . . . . .
H8 H 1.0380 0.4129 0.6625 0.038 Uiso 1 1 calc R . . . .
C22 C -0.0037(2) 0.28702(18) 0.25798(10) 0.0369(5) Uani 1 1 d . . . . .
H22 H -0.0903 0.2383 0.2627 0.044 Uiso 1 1 calc R . . . .
C21 C 0.1440(3) 0.24751(18) 0.27732(10) 0.0362(4) Uani 1 1 d . . . . .
H21 H 0.1582 0.1714 0.2950 0.043 Uiso 1 1 calc R . . . .
C12 C 1.0710(3) 0.13843(18) 0.49685(10) 0.0383(5) Uani 1 1 d . . . . .
H12 H 1.0904 0.0769 0.4690 0.046 Uiso 1 1 calc R . . . .
C27 C 0.6459(2) 0.32596(19) 0.12393(11) 0.0397(5) Uani 1 1 d . . . . .
H27 H 0.6865 0.2485 0.1233 0.048 Uiso 1 1 calc R . . . .
C14 C 0.8789(3) 0.22613(18) 0.41741(9) 0.0350(4) Uani 1 1 d . . . . .
H14 H 0.8939 0.1639 0.3894 0.042 Uiso 1 1 calc R . . . .
C23 C -0.0244(2) 0.39727(19) 0.23183(10) 0.0370(5) Uani 1 1 d . . . . .
H23 H -0.1256 0.4244 0.2187 0.044 Uiso 1 1 calc R . . . .
C10 C 1.1229(2) 0.22885(19) 0.59719(9) 0.0369(5) Uani 1 1 d . . . . .
H10 H 1.1777 0.2293 0.6375 0.044 Uiso 1 1 calc R . . . .
C11 C 1.1501(3) 0.14054(19) 0.55586(11) 0.0419(5) Uani 1 1 d . . . . .
H11 H 1.2234 0.0809 0.5679 0.050 Uiso 1 1 calc R . . . .
C28 C 0.6615(3) 0.4013(2) 0.07479(11) 0.0458(5) Uani 1 1 d . . . . .
H28 H 0.7130 0.3756 0.0405 0.055 Uiso 1 1 calc R . . . .
C29 C 0.6023(3) 0.5138(2) 0.07539(11) 0.0462(5) Uani 1 1 d . . . . .
H29 H 0.6133 0.5651 0.0415 0.055 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
P1 O1 1.4831(13) . ?
P1 C25 1.8003(18) . ?
P1 C19 1.8020(18) . ?
P1 C1 1.750(2) . ?
C17 C16 1.422(2) . ?
C17 C18 1.423(3) . ?
C17 C6 1.422(2) . ?
C16 C3 1.409(3) . ?
C16 C15 1.437(3) . ?
C18 C13 1.424(3) . ?
C18 C9 1.418(3) . ?
C25 C30 1.396(3) . ?
C25 C26 1.396(3) . ?
C19 C24 1.387(3) . ?
C19 C20 1.401(3) . ?
C6 C5 1.404(3) . ?
C6 C7 1.429(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.379(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.378(3) . ?
C2 C3 1.433(3) . ?
C2 C1 1.205(3) . ?
C30 H30 0.9500 . ?
C30 C29 1.386(3) . ?
C3 C4 1.401(3) . ?
C13 C12 1.392(3) . ?
C13 C14 1.435(3) . ?
C4 H4 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.386(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.355(3) . ?
C9 C8 1.431(3) . ?
C9 C10 1.402(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.347(3) . ?
C8 H8 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.386(3) . ?
C22 C23 1.380(3) . ?
C21 H21 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.388(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.382(3) . ?
C14 H14 0.9500 . ?
C23 H23 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.381(3) . ?
C11 H11 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.380(3) . ?
C29 H29 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
O1 P1 C25 111.49(8) . . ?
O1 P1 C19 112.58(8) . . ?
O1 P1 C1 113.45(9) . . ?
C25 P1 C19 107.52(8) . . ?
C1 P1 C25 107.92(9) . . ?
C1 P1 C19 103.39(9) . . ?
C16 C17 C18 120.07(16) . . ?
C16 C17 C6 120.24(17) . . ?
C6 C17 C18 119.67(16) . . ?
C17 C16 C15 118.56(17) . . ?
C3 C16 C17 118.62(17) . . ?
C3 C16 C15 122.81(17) . . ?
C17 C18 C13 120.12(17) . . ?
C9 C18 C17 120.32(16) . . ?
C9 C18 C13 119.55(17) . . ?
C30 C25 P1 117.09(14) . . ?
C26 C25 P1 123.25(14) . . ?
C26 C25 C30 119.60(17) . . ?
C24 C19 P1 117.20(14) . . ?
C24 C19 C20 119.56(17) . . ?
C20 C19 P1 123.20(14) . . ?
C17 C6 C7 118.85(17) . . ?
C5 C6 C17 118.97(16) . . ?
C5 C6 C7 122.17(17) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.41(18) . . ?
C23 C24 H24 119.8 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.42(19) . . ?
C21 C20 H20 120.3 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.00(17) . . ?
C4 C5 H5 119.5 . . ?
C1 C2 C3 179.1(2) . . ?
C25 C30 H30 120.2 . . ?
C29 C30 C25 119.7(2) . . ?
C29 C30 H30 120.2 . . ?
C16 C3 C2 119.83(18) . . ?
C4 C3 C16 120.54(17) . . ?
C4 C3 C2 119.61(18) . . ?
C2 C1 P1 169.21(19) . . ?
C18 C13 C14 118.08(18) . . ?
C12 C13 C18 119.15(18) . . ?
C12 C13 C14 122.77(18) . . ?
C5 C4 C3 120.58(18) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 119.93(19) . . ?
C27 C26 H26 120.0 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.20(17) . . ?
C8 C7 H7 119.4 . . ?
C18 C9 C8 118.49(17) . . ?
C10 C9 C18 119.11(18) . . ?
C10 C9 C8 122.39(18) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 C16 121.07(18) . . ?
C14 C15 H15 119.5 . . ?
C7 C8 C9 121.46(17) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C23 C22 C21 119.84(18) . . ?
C20 C21 C22 120.50(19) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C13 C12 H12 119.5 . . ?
C11 C12 C13 120.96(19) . . ?
C11 C12 H12 119.5 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.02(18) . . ?
C15 C14 H14 119.0 . . ?
C24 C23 C22 120.27(19) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.82(19) . . ?
C11 C10 H10 119.6 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.1(2) . . ?
C29 C28 H28 119.9 . . ?
C30 C29 H29 119.8 . . ?
C28 C29 C30 120.5(2) . . ?
C28 C29 H29 119.8 . . ?

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
P1 C25 C30 C29 -177.46(17) . . . . ?
P1 C25 C26 C27 177.11(15) . . . . ?
P1 C19 C24 C23 -177.39(15) . . . . ?
P1 C19 C20 C21 177.91(15) . . . . ?
O1 P1 C25 C30 -0.70(18) . . . . ?
O1 P1 C25 C26 -177.84(15) . . . . ?
O1 P1 C19 C24 14.30(17) . . . . ?
O1 P1 C19 C20 -163.72(15) . . . . ?
O1 P1 C1 C2 68.7(10) . . . . ?
C17 C16 C3 C2 176.26(17) . . . . ?
C17 C16 C3 C4 -2.4(3) . . . . ?
C17 C16 C15 C14 -1.9(3) . . . . ?
C17 C18 C13 C12 178.66(17) . . . . ?
C17 C18 C13 C14 -1.7(3) . . . . ?
C17 C18 C9 C8 1.0(3) . . . . ?
C17 C18 C9 C10 -178.43(17) . . . . ?
C17 C6 C5 C4 -1.4(3) . . . . ?
C17 C6 C7 C8 1.3(3) . . . . ?
C16 C17 C18 C13 -0.9(3) . . . . ?
C16 C17 C18 C9 177.76(16) . . . . ?
C16 C17 C6 C5 0.0(3) . . . . ?
C16 C17 C6 C7 -178.87(16) . . . . ?
C16 C3 C4 C5 1.0(3) . . . . ?
C16 C15 C14 C13 -0.7(3) . . . . ?
C18 C17 C16 C3 -176.42(17) . . . . ?
C18 C17 C16 C15 2.7(3) . . . . ?
C18 C17 C6 C5 178.31(17) . . . . ?
C18 C17 C6 C7 -0.6(3) . . . . ?
C18 C13 C12 C11 -0.3(3) . . . . ?
C18 C13 C14 C15 2.6(3) . . . . ?
C18 C9 C8 C7 -0.3(3) . . . . ?
C18 C9 C10 C11 -0.2(3) . . . . ?
C25 P1 C19 C24 -108.88(15) . . . . ?
C25 P1 C19 C20 73.10(17) . . . . ?
C25 P1 C1 C2 -167.3(10) . . . . ?
C25 C30 C29 C28 0.2(4) . . . . ?
C25 C26 C27 C28 0.2(3) . . . . ?
C19 P1 C25 C30 123.15(15) . . . . ?
C19 P1 C25 C26 -53.99(17) . . . . ?
C19 P1 C1 C2 -53.6(10) . . . . ?
C19 C24 C23 C22 -0.7(3) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C6 C17 C16 C3 1.8(3) . . . . ?
C6 C17 C16 C15 -179.06(17) . . . . ?
C6 C17 C18 C13 -179.13(16) . . . . ?
C6 C17 C18 C9 -0.5(3) . . . . ?
C6 C5 C4 C3 0.9(3) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C24 C19 C20 C21 -0.1(3) . . . . ?
C20 C19 C24 C23 0.7(3) . . . . ?
C5 C6 C7 C8 -177.59(19) . . . . ?
C2 C3 C4 C5 -177.61(18) . . . . ?
C30 C25 C26 C27 0.0(3) . . . . ?
C3 C16 C15 C14 177.14(19) . . . . ?
C1 P1 C25 C30 -125.93(16) . . . . ?
C1 P1 C25 C26 56.94(18) . . . . ?
C1 P1 C19 C24 137.12(15) . . . . ?
C1 P1 C19 C20 -40.90(17) . . . . ?
C13 C18 C9 C8 179.60(17) . . . . ?
C13 C18 C9 C10 0.2(3) . . . . ?
C13 C12 C11 C10 0.3(3) . . . . ?
C26 C25 C30 C29 -0.2(3) . . . . ?
C26 C27 C28 C29 -0.2(4) . . . . ?
C7 C6 C5 C4 177.43(18) . . . . ?
C9 C18 C13 C12 0.0(3) . . . . ?
C9 C18 C13 C14 179.65(17) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C15 C16 C3 C2 -2.8(3) . . . . ?
C15 C16 C3 C4 178.55(18) . . . . ?
C8 C9 C10 C11 -179.56(19) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C12 C13 C14 C15 -177.8(2) . . . . ?
C27 C28 C29 C30 0.0(4) . . . . ?
C14 C13 C12 C11 -179.9(2) . . . . ?
C23 C22 C21 C20 0.5(3) . . . . ?
C10 C9 C8 C7 179.08(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method loop
_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 1.465
_oxdiff_exptl_absorpt_empirical_full_min 0.702
####################################################################### 
# 
# 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_1478
_database_code_depnum_ccdc_archive 'CCDC 2432550'
loop_
_audit_author_name
_audit_author_address
'Kosuke Katagiri'
;Konan University
Japan
;
_audit_update_record             
;
2025-03-19 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;
_audit_creation_date             2024-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H19 O P'
_chemical_formula_sum            'C28 H19 O P'
_chemical_formula_weight         402.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C28H19OP
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8161(8)
_cell_length_b                   10.1226(5)
_cell_length_c                   11.6958(9)
_cell_angle_alpha                109.508(5)
_cell_angle_beta                 99.186(7)
_cell_angle_gamma                93.455(6)
_cell_volume                     1073.31(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4012
_cell_measurement_temperature    298
_cell_measurement_theta_max      76.5460
_cell_measurement_theta_min      4.0610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9155
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         89.419
_diffrn_reflns_theta_min         4.085
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00  85.00   0.50    0.50    --    0.00  37.00 120.00  110
  2  ω    -87.00 -60.00   0.50    0.50    --    0.00 -57.00 169.00   54
  3  ω    -77.00  27.00   0.50    0.50    --    0.00 -37.00-150.00  208
  4  ω    -27.00  17.00   0.50    0.50    --    0.00  37.00 120.00   88
  5  ω    -89.00 -17.00   0.50    0.50    --    0.00 -57.00 150.00  144
  6  ω     99.00 186.00   0.50    1.39    --  101.00  30.00-120.00  174
  7  ω     12.00 113.00   0.50    1.39    --  101.00 -82.00 -60.00  202
  8  ω     96.00 190.00   0.50    1.39    --  101.00  45.00  90.00  188
  9  ω    103.00 129.00   0.50    1.39    --  101.00 -82.00-150.00   52
 10  ω     51.00 100.00   0.50    1.39    --  101.00 -82.00-150.00   98
 11  ω     76.00 102.00   0.50    1.39    --  101.00 -82.00 150.00   52
 12  ω    116.00 190.00   0.50    1.39    --  101.00  45.00 120.00  148
 13  ω    114.00 186.00   0.50    1.39    --  101.00  45.00-180.00  144
 14  ω     37.00 111.00   0.50    1.39    --  101.00 -61.00-150.00  148
 15  ω     23.00 131.00   0.50    1.39    --  101.00 -82.00  90.00  216
 16  ω     53.00 126.00   0.50    1.39    --  101.00 -61.00  60.00  146
 17  ω     75.00 134.00   0.50    1.39    --  101.00  45.00-150.00  118
 18  ω    140.00 171.00   0.50    1.39    --  101.00  45.00-150.00   62
 19  ω     19.00  44.00   0.50    1.39    --  101.00 -82.00 150.00   50
 20  ω     76.00 115.00   0.50    1.39    --  101.00 -82.00 -30.00   78
 21  ω     19.00 116.00   0.50    1.39    --  101.00 -61.00 -30.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1260722000
_diffrn_orient_matrix_UB_12      0.1152037000
_diffrn_orient_matrix_UB_13      0.0484959000
_diffrn_orient_matrix_UB_21      -0.0845445000
_diffrn_orient_matrix_UB_22      0.0999706000
_diffrn_orient_matrix_UB_23      0.0838766000
_diffrn_orient_matrix_UB_31      0.0511395000
_diffrn_orient_matrix_UB_32      -0.0565416000
_diffrn_orient_matrix_UB_33      0.1043077000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2808
_reflns_number_total             4252
_reflns_odcompleteness_completeness 96.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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         0.389
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0809
_refine_ls_restrained_S_all      1.184
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2471
_refine_ls_wR_factor_ref         0.3249
_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:
 C22(H22), C15(H15), C28(H28), C18(H18), C21(H21), C5(H5), C10(H10), C20(H20),
 C24(H24), C19(H19), C8(H8), C26(H26), C27(H27), C25(H25), C6(H6), C13(H13),
 C14(H14), C12(H12), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
P1 P 0.21999(9) 0.69707(10) 0.20418(9) 0.0635(4) Uani 1 1 d . . . . .
O1 O 0.0800(3) 0.6966(3) 0.1372(3) 0.0834(9) Uani 1 1 d . . . . .
C3 C 0.1707(4) 0.6432(4) 0.5486(4) 0.0621(9) Uani 1 1 d . . . . .
C23 C 0.3357(4) 0.8500(4) 0.2216(4) 0.0639(9) Uani 1 1 d . . . . .
C16 C 0.1934(4) 0.5097(4) 0.5563(4) 0.0664(9) Uani 1 1 d . . . . .
C4 C 0.1134(4) 0.7424(4) 0.6390(4) 0.0670(9) Uani 1 1 d . . . . .
C17 C 0.3000(4) 0.5434(4) 0.1330(4) 0.0618(8) Uani 1 1 d . . . . .
C2 C 0.1991(4) 0.6742(4) 0.4432(4) 0.0650(9) Uani 1 1 d . . . . .
C22 C 0.2210(4) 0.4332(4) 0.0348(4) 0.0715(10) Uani 1 1 d . . . . .
H22 H 0.1279 0.4392 0.0080 0.086 Uiso 1 1 calc R . . . .
C9 C 0.0790(4) 0.7071(5) 0.7405(4) 0.0774(11) Uani 1 1 d . . . . .
C15 C 0.2510(5) 0.4077(5) 0.4676(5) 0.0833(12) Uani 1 1 d . . . . .
H15 H 0.2782 0.4291 0.4026 0.100 Uiso 1 1 calc R . . . .
C28 C 0.4454(4) 0.9088(4) 0.3183(4) 0.0755(11) Uani 1 1 d . . . . .
H28 H 0.4618 0.8708 0.3808 0.091 Uiso 1 1 calc R . . . .
C18 C 0.4382(4) 0.5306(5) 0.1727(4) 0.0794(11) Uani 1 1 d . . . . .
H18 H 0.4920 0.6027 0.2396 0.095 Uiso 1 1 calc R . . . .
C11 C 0.1537(4) 0.4756(5) 0.6563(4) 0.0761(11) Uani 1 1 d . . . . .
C1 C 0.2215(4) 0.6967(4) 0.3532(4) 0.0717(10) Uani 1 1 d . . . . .
C21 C 0.2797(5) 0.3158(4) -0.0228(4) 0.0803(11) Uani 1 1 d . . . . .
H21 H 0.2260 0.2421 -0.0884 0.096 Uiso 1 1 calc R . . . .
C5 C 0.0894(5) 0.8790(4) 0.6358(4) 0.0803(11) Uani 1 1 d . . . . .
H5 H 0.1114 0.9052 0.5712 0.096 Uiso 1 1 calc R . . . .
C10 C 0.0969(5) 0.5741(6) 0.7449(4) 0.0857(12) Uani 1 1 d . . . . .
H10 H 0.0703 0.5499 0.8088 0.103 Uiso 1 1 calc R . . . .
C20 C 0.4165(6) 0.3058(5) 0.0151(5) 0.0872(14) Uani 1 1 d . . . . .
H20 H 0.4561 0.2265 -0.0261 0.105 Uiso 1 1 calc R . . . .
C24 C 0.3134(5) 0.9067(5) 0.1282(5) 0.0837(13) Uani 1 1 d . . . . .
H24 H 0.2408 0.8662 0.0610 0.100 Uiso 1 1 calc R . . . .
C19 C 0.4957(5) 0.4125(5) 0.1139(5) 0.0878(13) Uani 1 1 d . . . . .
H19 H 0.5883 0.4046 0.1408 0.105 Uiso 1 1 calc R . . . .
C8 C 0.0221(5) 0.8106(7) 0.8315(5) 0.1009(16) Uani 1 1 d . . . . .
H8 H -0.0017 0.7893 0.8978 0.121 Uiso 1 1 calc R . . . .
C26 C 0.5089(6) 1.0815(5) 0.2316(6) 0.1014(17) Uani 1 1 d . . . . .
H26 H 0.5670 1.1590 0.2345 0.122 Uiso 1 1 calc R . . . .
C27 C 0.5328(5) 1.0258(5) 0.3233(5) 0.0961(15) Uani 1 1 d . . . . .
H27 H 0.6072 1.0656 0.3891 0.115 Uiso 1 1 calc R . . . .
C25 C 0.3990(6) 1.0228(6) 0.1354(6) 0.1012(16) Uani 1 1 d . . . . .
H25 H 0.3820 1.0622 0.0739 0.121 Uiso 1 1 calc R . . . .
C6 C 0.0352(5) 0.9709(5) 0.7250(5) 0.1006(16) Uani 1 1 d . . . . .
H6 H 0.0196 1.0588 0.7204 0.121 Uiso 1 1 calc R . . . .
C13 C 0.2252(6) 0.2446(6) 0.5748(7) 0.1110(19) Uani 1 1 d . . . . .
H13 H 0.2353 0.1558 0.5798 0.133 Uiso 1 1 calc R . . . .
C14 C 0.2670(6) 0.2778(5) 0.4766(6) 0.1076(17) Uani 1 1 d . . . . .
H14 H 0.3053 0.2117 0.4181 0.129 Uiso 1 1 calc R . . . .
C12 C 0.1713(6) 0.3384(6) 0.6608(6) 0.1006(16) Uani 1 1 d . . . . .
H12 H 0.1449 0.3139 0.7247 0.121 Uiso 1 1 calc R . . . .
C7 C 0.0026(6) 0.9362(7) 0.8234(6) 0.114(2) Uani 1 1 d . . . . .
H7 H -0.0333 1.0016 0.8845 0.137 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
P1 O1 1.468(3) . ?
P1 C23 1.798(4) . ?
P1 C17 1.795(4) . ?
P1 C1 1.742(4) . ?
C3 C16 1.413(5) . ?
C3 C4 1.410(5) . ?
C3 C2 1.433(5) . ?
C23 C28 1.370(6) . ?
C23 C24 1.389(5) . ?
C16 C15 1.416(5) . ?
C16 C11 1.427(5) . ?
C4 C9 1.431(5) . ?
C4 C5 1.429(5) . ?
C17 C22 1.386(5) . ?
C17 C18 1.390(5) . ?
C2 C1 1.198(5) . ?
C22 H22 0.9300 . ?
C22 C21 1.368(6) . ?
C9 C10 1.385(7) . ?
C9 C8 1.435(6) . ?
C15 H15 0.9300 . ?
C15 C14 1.369(6) . ?
C28 H28 0.9300 . ?
C28 C27 1.399(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(6) . ?
C11 C10 1.393(6) . ?
C11 C12 1.427(6) . ?
C21 H21 0.9300 . ?
C21 C20 1.366(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.351(6) . ?
C10 H10 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.373(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.373(7) . ?
C19 H19 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.328(9) . ?
C26 H26 0.9300 . ?
C26 C27 1.365(7) . ?
C26 C25 1.368(8) . ?
C27 H27 0.9300 . ?
C25 H25 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.387(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.412(8) . ?
C13 C12 1.336(8) . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
C7 H7 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
O1 P1 C23 112.43(18) . . ?
O1 P1 C17 113.30(18) . . ?
O1 P1 C1 113.04(19) . . ?
C17 P1 C23 107.87(15) . . ?
C1 P1 C23 105.80(19) . . ?
C1 P1 C17 103.74(18) . . ?
C16 C3 C2 119.0(3) . . ?
C4 C3 C16 121.1(3) . . ?
C4 C3 C2 119.9(3) . . ?
C28 C23 P1 123.8(3) . . ?
C28 C23 C24 119.3(4) . . ?
C24 C23 P1 116.9(3) . . ?
C3 C16 C15 122.7(4) . . ?
C3 C16 C11 118.4(4) . . ?
C15 C16 C11 118.9(4) . . ?
C3 C4 C9 119.3(4) . . ?
C3 C4 C5 123.2(4) . . ?
C5 C4 C9 117.5(4) . . ?
C22 C17 P1 118.7(3) . . ?
C22 C17 C18 118.7(4) . . ?
C18 C17 P1 122.5(3) . . ?
C1 C2 C3 178.3(4) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.1(4) . . ?
C21 C22 H22 119.9 . . ?
C4 C9 C8 118.0(4) . . ?
C10 C9 C4 119.2(4) . . ?
C10 C9 C8 122.7(5) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.7(5) . . ?
C14 C15 H15 119.7 . . ?
C23 C28 H28 119.9 . . ?
C23 C28 C27 120.2(4) . . ?
C27 C28 H28 119.9 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.7 . . ?
C16 C11 C12 118.2(5) . . ?
C10 C11 C16 120.0(4) . . ?
C10 C11 C12 121.7(5) . . ?
C2 C1 P1 166.0(4) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 C22 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(5) . . ?
C6 C5 H5 119.5 . . ?
C9 C10 C11 121.9(4) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C21 C20 H20 119.9 . . ?
C21 C20 C19 120.1(4) . . ?
C19 C20 H20 119.9 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.8(5) . . ?
C25 C24 H24 120.1 . . ?
C18 C19 C20 119.9(4) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C9 C8 H8 119.2 . . ?
C7 C8 C9 121.6(5) . . ?
C7 C8 H8 119.2 . . ?
C27 C26 H26 120.1 . . ?
C27 C26 C25 119.8(4) . . ?
C25 C26 H26 120.1 . . ?
C28 C27 H27 120.1 . . ?
C26 C27 C28 119.9(5) . . ?
C26 C27 H27 120.1 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.0(4) . . ?
C26 C25 H25 119.5 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.1(5) . . ?
C7 C6 H6 119.4 . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(5) . . ?
C15 C14 C13 119.9(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.1(5) . . ?
C13 C12 H12 119.4 . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?

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
P1 C23 C28 C27 178.3(3) . . . . ?
P1 C23 C24 C25 -179.4(3) . . . . ?
P1 C17 C22 C21 178.8(3) . . . . ?
P1 C17 C18 C19 -178.6(3) . . . . ?
O1 P1 C23 C28 151.0(3) . . . . ?
O1 P1 C23 C24 -31.3(3) . . . . ?
O1 P1 C17 C22 -8.0(4) . . . . ?
O1 P1 C17 C18 172.0(3) . . . . ?
O1 P1 C1 C2 46.1(15) . . . . ?
C3 C16 C15 C14 -177.9(4) . . . . ?
C3 C16 C11 C10 -1.4(6) . . . . ?
C3 C16 C11 C12 177.4(4) . . . . ?
C3 C4 C9 C10 -2.8(6) . . . . ?
C3 C4 C9 C8 179.4(4) . . . . ?
C3 C4 C5 C6 -179.5(4) . . . . ?
C23 P1 C17 C22 -133.1(3) . . . . ?
C23 P1 C17 C18 46.9(4) . . . . ?
C23 P1 C1 C2 169.5(14) . . . . ?
C23 C28 C27 C26 0.0(7) . . . . ?
C23 C24 C25 C26 1.9(7) . . . . ?
C16 C3 C4 C9 0.5(6) . . . . ?
C16 C3 C4 C5 179.6(4) . . . . ?
C16 C15 C14 C13 0.3(8) . . . . ?
C16 C11 C10 C9 -1.0(7) . . . . ?
C16 C11 C12 C13 0.9(7) . . . . ?
C4 C3 C16 C15 -179.8(4) . . . . ?
C4 C3 C16 C11 1.5(6) . . . . ?
C4 C9 C10 C11 3.0(7) . . . . ?
C4 C9 C8 C7 -0.6(8) . . . . ?
C4 C5 C6 C7 0.7(8) . . . . ?
C17 P1 C23 C28 -83.4(4) . . . . ?
C17 P1 C23 C24 94.3(3) . . . . ?
C17 P1 C1 C2 -77.1(14) . . . . ?
C17 C22 C21 C20 -0.3(6) . . . . ?
C17 C18 C19 C20 -0.1(7) . . . . ?
C2 C3 C16 C15 3.8(6) . . . . ?
C2 C3 C16 C11 -174.8(3) . . . . ?
C2 C3 C4 C9 176.8(3) . . . . ?
C2 C3 C4 C5 -4.1(6) . . . . ?
C22 C17 C18 C19 1.4(6) . . . . ?
C22 C21 C20 C19 1.7(6) . . . . ?
C9 C4 C5 C6 -0.4(7) . . . . ?
C9 C8 C7 C6 0.9(9) . . . . ?
C15 C16 C11 C10 179.9(4) . . . . ?
C15 C16 C11 C12 -1.3(6) . . . . ?
C28 C23 C24 C25 -1.7(6) . . . . ?
C18 C17 C22 C21 -1.2(6) . . . . ?
C11 C16 C15 C14 0.7(7) . . . . ?
C1 P1 C23 C28 27.2(4) . . . . ?
C1 P1 C23 C24 -155.2(3) . . . . ?
C1 P1 C17 C22 114.9(3) . . . . ?
C1 P1 C17 C18 -65.0(3) . . . . ?
C21 C20 C19 C18 -1.5(7) . . . . ?
C5 C4 C9 C10 178.1(4) . . . . ?
C5 C4 C9 C8 0.3(6) . . . . ?
C5 C6 C7 C8 -0.9(9) . . . . ?
C10 C9 C8 C7 -178.3(5) . . . . ?
C10 C11 C12 C13 179.6(5) . . . . ?
C24 C23 C28 C27 0.7(6) . . . . ?
C8 C9 C10 C11 -179.3(4) . . . . ?
C27 C26 C25 C24 -1.2(8) . . . . ?
C25 C26 C27 C28 0.3(8) . . . . ?
C14 C13 C12 C11 0.2(9) . . . . ?
C12 C11 C10 C9 -179.6(5) . . . . ?
C12 C13 C14 C15 -0.8(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method loop
_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 2.814
_oxdiff_exptl_absorpt_empirical_full_min 0.402
####################################################################### 
# 
# 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_1443
_database_code_depnum_ccdc_archive 'CCDC 2432551'
loop_
_audit_author_name
_audit_author_address
'Kosuke Katagiri'
;Konan Univeristy
Japan
;
_audit_update_record             
;
2025-03-19 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H23 O P'
_chemical_formula_sum            'C34 H23 O P'
_chemical_formula_weight         478.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         C34H23OP
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'
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                   17.2834(4)
_cell_length_b                   9.4529(2)
_cell_length_c                   14.7171(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.788(2)
_cell_angle_gamma                90
_cell_volume                     2369.48(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6449
_cell_measurement_temperature    173
_cell_measurement_theta_max      76.5860
_cell_measurement_theta_min      5.1830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13136
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.415
_diffrn_reflns_theta_min         5.194
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  56.00   0.50   27.10    --    0.00  37.00  90.00   50
  2  ω    -10.00  17.00   0.50   27.10    --    0.00  37.00  90.00   54
  3  ω    -26.00  89.00   0.50   27.10    --    0.00  37.00 150.00  230
  4  ω    -68.00   1.00   0.50   27.10    --    0.00 -37.00-180.00  138
  5  ω     84.00 178.00   0.50  108.42    --  101.00  45.00 -90.00  188
  6  ω     75.00 140.00   0.50  108.42    --  101.00  45.00 150.00  130
  7  ω     74.00 166.00   0.50  108.42    --  101.00  77.00 -60.00  184
  8  ω     75.00 190.00   0.50  108.42    --  101.00  45.00-150.00  230
  9  ω     95.00 178.00   0.50  108.42    --  101.00  45.00-120.00  166
 10  ω     82.00 108.00   0.50  108.42    --  101.00  45.00 120.00   52
 11  ω     61.00 126.00   0.50  108.42    --  101.00 -77.00-180.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0777497000
_diffrn_orient_matrix_UB_12      0.0439410000
_diffrn_orient_matrix_UB_13      -0.0609754000
_diffrn_orient_matrix_UB_21      -0.0457131000
_diffrn_orient_matrix_UB_22      -0.0928967000
_diffrn_orient_matrix_UB_23      0.0585378000
_diffrn_orient_matrix_UB_31      -0.0067989000
_diffrn_orient_matrix_UB_32      0.1264567000
_diffrn_orient_matrix_UB_33      0.0643434000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4160
_reflns_number_total             4881
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.049
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1352
_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:
 C2(H2), C3(H3), C6(H6), C5(H5), C12(H12), C14(H14), C15(H15), C21(H21),
 C18(H18), C31(H31), C20(H20), C8(H8), C16(H16), C30(H30), C11(H11), C17(H17),
 C9(H9), C23(H23), C10(H10), C24(H24), C28(H28), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
P1 P 0.08538(2) 0.19128(4) 0.22236(2) 0.02606(13) Uani 1 1 d . . . . .
O1 O 0.00234(6) 0.23732(12) 0.21257(7) 0.0338(3) Uani 1 1 d . . . . .
C2 C 0.11866(9) 0.47607(16) 0.23255(9) 0.0271(3) Uani 1 1 d . . . . .
H2 H 0.063267 0.486314 0.225290 0.033 Uiso 1 1 calc R U . . .
C3 C 0.16629(9) 0.59570(16) 0.24240(9) 0.0281(3) Uani 1 1 d . . . . .
H3 H 0.143155 0.686991 0.241192 0.034 Uiso 1 1 calc R U . . .
C13 C 0.10686(9) 0.08340(16) 0.12840(9) 0.0279(3) Uani 1 1 d . . . . .
C7 C 0.11525(9) 0.08781(16) 0.32523(10) 0.0279(3) Uani 1 1 d . . . . .
C1 C 0.15166(9) 0.34085(16) 0.23325(9) 0.0265(3) Uani 1 1 d . . . . .
C4 C 0.24770(9) 0.58249(16) 0.25402(9) 0.0285(3) Uani 1 1 d . . . . .
C6 C 0.23327(9) 0.32733(17) 0.24554(10) 0.0310(3) Uani 1 1 d . . . . .
H6 H 0.256477 0.236076 0.247042 0.037 Uiso 1 1 calc R U . . .
C32 C 0.36357(9) 0.72615(16) 0.33257(10) 0.0296(3) Uani 1 1 d . . . . .
C5 C 0.28048(9) 0.44688(17) 0.25556(11) 0.0327(3) Uani 1 1 d . . . . .
H5 H 0.335907 0.436594 0.263594 0.039 Uiso 1 1 calc R U . . .
C19 C 0.29972(9) 0.70940(17) 0.25931(10) 0.0299(3) Uani 1 1 d . . . . .
C33 C 0.41781(9) 0.83813(17) 0.32792(10) 0.0298(3) Uani 1 1 d . . . . .
C12 C 0.17776(10) -0.00649(18) 0.33582(11) 0.0337(3) Uani 1 1 d . . . . .
H12 H 0.205126 -0.023038 0.286044 0.040 Uiso 1 1 calc R U . . .
C14 C 0.06983(10) -0.04846(17) 0.11526(10) 0.0322(3) Uani 1 1 d . . . . .
H14 H 0.039787 -0.082959 0.158926 0.039 Uiso 1 1 calc R U . . .
C22 C 0.40501(10) 0.93681(18) 0.25377(11) 0.0331(3) Uani 1 1 d . . . . .
C15 C 0.07718(10) -0.12851(18) 0.03829(10) 0.0350(4) Uani 1 1 d . . . . .
H15 H 0.051956 -0.217928 0.029318 0.042 Uiso 1 1 calc R U . . .
C34 C 0.48675(9) 0.84936(18) 0.39640(10) 0.0332(3) Uani 1 1 d . . . . .
C21 C 0.33860(10) 0.92089(18) 0.18571(11) 0.0341(4) Uani 1 1 d . . . . .
H21 H 0.328296 0.987928 0.137063 0.041 Uiso 1 1 calc R U . . .
C29 C 0.50024(10) 0.75161(19) 0.47106(11) 0.0364(4) Uani 1 1 d . . . . .
C18 C 0.15200(10) 0.13106(18) 0.06468(10) 0.0334(3) Uani 1 1 d . . . . .
H18 H 0.178202 0.219588 0.073644 0.040 Uiso 1 1 calc R U . . .
C31 C 0.37594(10) 0.63646(18) 0.41234(11) 0.0346(4) Uani 1 1 d . . . . .
H31 H 0.337929 0.566390 0.419104 0.042 Uiso 1 1 calc R U . . .
C20 C 0.28770(9) 0.80869(17) 0.18834(11) 0.0328(3) Uani 1 1 d . . . . .
H20 H 0.243494 0.799080 0.140642 0.039 Uiso 1 1 calc R U . . .
C8 C 0.07505(10) 0.10935(19) 0.39844(11) 0.0365(4) Uani 1 1 d . . . . .
H8 H 0.031521 0.172132 0.391418 0.044 Uiso 1 1 calc R U . . .
C16 C 0.12078(11) -0.07949(18) -0.02537(10) 0.0369(4) Uani 1 1 d . . . . .
H16 H 0.124678 -0.134392 -0.078474 0.044 Uiso 1 1 calc R U . . .
C25 C 0.54295(10) 0.9564(2) 0.38952(12) 0.0389(4) Uani 1 1 d . . . . .
C30 C 0.44048(10) 0.64932(19) 0.47817(11) 0.0368(4) Uani 1 1 d . . . . .
H30 H 0.446298 0.588910 0.530478 0.044 Uiso 1 1 calc R U . . .
C11 C 0.20035(11) -0.07663(19) 0.41900(12) 0.0396(4) Uani 1 1 d . . . . .
H11 H 0.242687 -0.142030 0.426002 0.048 Uiso 1 1 calc R U . . .
C17 C 0.15874(11) 0.04902(19) -0.01214(10) 0.0377(4) Uani 1 1 d . . . . .
H17 H 0.189562 0.081660 -0.055542 0.045 Uiso 1 1 calc R U . . .
C9 C 0.09810(11) 0.0400(2) 0.48112(11) 0.0407(4) Uani 1 1 d . . . . .
H9 H 0.070415 0.055172 0.530778 0.049 Uiso 1 1 calc R U . . .
C23 C 0.46162(11) 1.0481(2) 0.25130(12) 0.0402(4) Uani 1 1 d . . . . .
H23 H 0.452796 1.116467 0.203322 0.048 Uiso 1 1 calc R U . . .
C10 C 0.16087(11) -0.0508(2) 0.49176(11) 0.0408(4) Uani 1 1 d . . . . .
H10 H 0.177386 -0.096280 0.549355 0.049 Uiso 1 1 calc R U . . .
C24 C 0.52671(11) 1.0570(2) 0.31573(12) 0.0428(4) Uani 1 1 d . . . . .
H24 H 0.562853 1.131692 0.312285 0.051 Uiso 1 1 calc R U . . .
C28 C 0.56985(11) 0.7601(2) 0.53449(13) 0.0461(4) Uani 1 1 d . . . . .
H28 H 0.579210 0.695521 0.584606 0.055 Uiso 1 1 calc R U . . .
C26 C 0.61199(11) 0.9603(2) 0.45398(14) 0.0488(5) Uani 1 1 d . . . . .
H26 H 0.650214 1.030908 0.449238 0.059 Uiso 1 1 calc R U . . .
C27 C 0.62557(12) 0.8623(2) 0.52492(14) 0.0515(5) Uani 1 1 d . . . . .
H27 H 0.673501 0.865111 0.567455 0.062 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
P1 O1 1.4832(11) . ?
P1 C13 1.8067(15) . ?
P1 C7 1.8027(15) . ?
P1 C1 1.8095(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(2) . ?
C2 C1 1.399(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(2) . ?
C13 C14 1.399(2) . ?
C13 C18 1.393(2) . ?
C7 C12 1.389(2) . ?
C7 C8 1.393(2) . ?
C1 C6 1.397(2) . ?
C4 C5 1.400(2) . ?
C4 C19 1.493(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.387(2) . ?
C32 C19 1.414(2) . ?
C32 C33 1.423(2) . ?
C32 C31 1.434(2) . ?
C5 H5 0.9500 . ?
C19 C20 1.393(2) . ?
C33 C22 1.424(2) . ?
C33 C34 1.428(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.389(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C22 C21 1.397(2) . ?
C22 C23 1.442(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(2) . ?
C34 C29 1.424(2) . ?
C34 C25 1.418(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.383(2) . ?
C29 C30 1.432(2) . ?
C29 C28 1.394(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.392(2) . ?
C31 H31 0.9500 . ?
C31 C30 1.353(2) . ?
C20 H20 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.380(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(2) . ?
C25 C24 1.434(3) . ?
C25 C26 1.393(2) . ?
C30 H30 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.386(3) . ?
C17 H17 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.371(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.345(3) . ?
C10 H10 0.9500 . ?
C24 H24 0.9500 . ?
C28 H28 0.9500 . ?
C28 C27 1.388(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.386(3) . ?
C27 H27 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
O1 P1 C13 114.37(7) . . ?
O1 P1 C7 112.02(7) . . ?
O1 P1 C1 111.52(7) . . ?
C13 P1 C1 107.43(7) . . ?
C7 P1 C13 105.65(7) . . ?
C7 P1 C1 105.25(7) . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.56(13) . . ?
C1 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.46(14) . . ?
C4 C3 H3 119.8 . . ?
C14 C13 P1 117.38(11) . . ?
C18 C13 P1 122.97(12) . . ?
C18 C13 C14 119.37(14) . . ?
C12 C7 P1 123.28(11) . . ?
C12 C7 C8 119.20(14) . . ?
C8 C7 P1 117.46(12) . . ?
C2 C1 P1 117.52(11) . . ?
C6 C1 P1 123.37(12) . . ?
C6 C1 C2 119.07(14) . . ?
C3 C4 C5 118.77(14) . . ?
C3 C4 C19 121.38(14) . . ?
C5 C4 C19 119.75(13) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.14(14) . . ?
C5 C6 H6 119.9 . . ?
C19 C32 C33 118.78(14) . . ?
C19 C32 C31 123.10(14) . . ?
C33 C32 C31 118.11(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.00(14) . . ?
C6 C5 H5 119.5 . . ?
C32 C19 C4 120.97(14) . . ?
C20 C19 C4 119.36(13) . . ?
C20 C19 C32 119.57(14) . . ?
C32 C33 C22 120.41(14) . . ?
C32 C33 C34 119.92(14) . . ?
C22 C33 C34 119.64(14) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.14(15) . . ?
C11 C12 H12 119.9 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.73(14) . . ?
C15 C14 H14 120.1 . . ?
C33 C22 C23 118.67(15) . . ?
C21 C22 C33 118.71(14) . . ?
C21 C22 C23 122.61(15) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.57(15) . . ?
C16 C15 H15 119.7 . . ?
C29 C34 C33 120.26(15) . . ?
C25 C34 C33 120.14(15) . . ?
C25 C34 C29 119.59(15) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.76(15) . . ?
C20 C21 H21 119.6 . . ?
C34 C29 C30 117.97(15) . . ?
C28 C29 C34 119.26(17) . . ?
C28 C29 C30 122.76(17) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.03(15) . . ?
C17 C18 H18 120.0 . . ?
C32 C31 H31 119.2 . . ?
C30 C31 C32 121.54(15) . . ?
C30 C31 H31 119.2 . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.55(15) . . ?
C21 C20 H20 119.2 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.36(16) . . ?
C9 C8 H8 119.8 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.15(15) . . ?
C17 C16 H16 119.9 . . ?
C34 C25 C24 118.59(15) . . ?
C26 C25 C34 119.20(17) . . ?
C26 C25 C24 122.21(17) . . ?
C29 C30 H30 119.1 . . ?
C31 C30 C29 121.71(15) . . ?
C31 C30 H30 119.1 . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.70(17) . . ?
C10 C11 H11 120.1 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.13(15) . . ?
C16 C17 H17 119.9 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.15(15) . . ?
C10 C9 H9 119.9 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.16(17) . . ?
C24 C23 H23 119.4 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.40(15) . . ?
C9 C10 H10 119.8 . . ?
C25 C24 H24 119.2 . . ?
C23 C24 C25 121.68(16) . . ?
C23 C24 H24 119.2 . . ?
C29 C28 H28 119.8 . . ?
C27 C28 C29 120.46(18) . . ?
C27 C28 H28 119.8 . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.76(18) . . ?
C27 C26 H26 119.6 . . ?
C28 C27 H27 119.7 . . ?
C26 C27 C28 120.67(17) . . ?
C26 C27 H27 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
P1 C13 C14 C15 172.76(12) . . . . ?
P1 C13 C18 C17 -172.48(13) . . . . ?
P1 C7 C12 C11 176.26(13) . . . . ?
P1 C7 C8 C9 -176.01(13) . . . . ?
P1 C1 C6 C5 -178.46(11) . . . . ?
O1 P1 C13 C14 -64.05(14) . . . . ?
O1 P1 C13 C18 109.79(14) . . . . ?
O1 P1 C7 C12 157.30(13) . . . . ?
O1 P1 C7 C8 -25.49(15) . . . . ?
O1 P1 C1 C2 0.85(13) . . . . ?
O1 P1 C1 C6 178.44(11) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C2 C3 C4 C19 176.45(13) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C3 C2 C1 P1 178.77(10) . . . . ?
C3 C2 C1 C6 1.1(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C3 C4 C19 C32 128.53(15) . . . . ?
C3 C4 C19 C20 -55.0(2) . . . . ?
C13 P1 C7 C12 32.15(15) . . . . ?
C13 P1 C7 C8 -150.63(13) . . . . ?
C13 P1 C1 C2 126.92(11) . . . . ?
C13 P1 C1 C6 -55.49(14) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C13 C18 C17 C16 0.0(3) . . . . ?
C7 P1 C13 C14 59.63(13) . . . . ?
C7 P1 C13 C18 -126.54(14) . . . . ?
C7 P1 C1 C2 -120.84(11) . . . . ?
C7 P1 C1 C6 56.76(13) . . . . ?
C7 C12 C11 C10 -0.8(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C1 P1 C13 C14 171.60(11) . . . . ?
C1 P1 C13 C18 -14.56(16) . . . . ?
C1 P1 C7 C12 -81.34(14) . . . . ?
C1 P1 C7 C8 95.87(13) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C1 C6 C5 C4 0.3(2) . . . . ?
C4 C19 C20 C21 -173.91(14) . . . . ?
C32 C19 C20 C21 2.6(2) . . . . ?
C32 C33 C22 C21 -0.4(2) . . . . ?
C32 C33 C22 C23 -179.61(15) . . . . ?
C32 C33 C34 C29 -2.0(2) . . . . ?
C32 C33 C34 C25 176.81(14) . . . . ?
C32 C31 C30 C29 -0.9(3) . . . . ?
C5 C4 C19 C32 -55.1(2) . . . . ?
C5 C4 C19 C20 121.37(16) . . . . ?
C19 C4 C5 C6 -176.34(14) . . . . ?
C19 C32 C33 C22 4.1(2) . . . . ?
C19 C32 C33 C34 -174.05(14) . . . . ?
C19 C32 C31 C30 175.44(16) . . . . ?
C33 C32 C19 C4 171.30(13) . . . . ?
C33 C32 C19 C20 -5.1(2) . . . . ?
C33 C32 C31 C30 -5.3(2) . . . . ?
C33 C22 C21 C20 -2.3(2) . . . . ?
C33 C22 C23 C24 2.1(3) . . . . ?
C33 C34 C29 C30 -4.1(2) . . . . ?
C33 C34 C29 C28 176.73(16) . . . . ?
C33 C34 C25 C24 3.5(2) . . . . ?
C33 C34 C25 C26 -176.18(16) . . . . ?
C12 C7 C8 C9 1.3(2) . . . . ?
C12 C11 C10 C9 2.1(3) . . . . ?
C14 C13 C18 C17 1.2(2) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C22 C33 C34 C29 179.86(14) . . . . ?
C22 C33 C34 C25 -1.3(2) . . . . ?
C22 C21 C20 C19 1.2(2) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C34 C33 C22 C21 177.74(14) . . . . ?
C34 C33 C22 C23 -1.5(2) . . . . ?
C34 C29 C30 C31 5.6(2) . . . . ?
C34 C29 C28 C27 -0.2(3) . . . . ?
C34 C25 C24 C23 -3.0(3) . . . . ?
C34 C25 C26 C27 -0.9(3) . . . . ?
C21 C22 C23 C24 -177.08(17) . . . . ?
C29 C34 C25 C24 -177.66(16) . . . . ?
C29 C34 C25 C26 2.6(3) . . . . ?
C29 C28 C27 C26 2.0(3) . . . . ?
C18 C13 C14 C15 -1.3(2) . . . . ?
C31 C32 C19 C4 -9.5(2) . . . . ?
C31 C32 C19 C20 174.08(15) . . . . ?
C31 C32 C33 C22 -175.20(14) . . . . ?
C31 C32 C33 C34 6.7(2) . . . . ?
C8 C7 C12 C11 -0.9(2) . . . . ?
C8 C9 C10 C11 -1.7(3) . . . . ?
C25 C34 C29 C30 177.06(15) . . . . ?
C25 C34 C29 C28 -2.1(2) . . . . ?
C25 C26 C27 C28 -1.5(3) . . . . ?
C30 C29 C28 C27 -179.33(18) . . . . ?
C23 C22 C21 C20 176.91(16) . . . . ?
C24 C25 C26 C27 179.43(19) . . . . ?
C28 C29 C30 C31 -175.23(18) . . . . ?
C26 C25 C24 C23 176.72(19) . . . . ?

_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 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.871
