####################################################################### 
# 
# 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_xu_220307
_database_code_depnum_ccdc_archive 'CCDC 2166424'
loop_
_audit_author_name
_audit_author_address
'Shibo Xu'
;Osaka University
Japan
;
_audit_update_record             
;
2022-04-14 deposited with the CCDC.	2022-09-06 downloaded from the CCDC.
;
_audit_creation_date             2022-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H18 O P, 2(C H Cl3)'
_chemical_formula_sum            'C30 H20 Cl6 O P'
_chemical_formula_weight         640.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C60 H40 O2 P2 Cl12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.0941(3)
_cell_length_b                   10.4249(3)
_cell_length_c                   15.3161(3)
_cell_angle_alpha                73.955(2)
_cell_angle_beta                 87.469(2)
_cell_angle_gamma                73.633(3)
_cell_volume                     1485.17(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9019
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.0410
_cell_measurement_theta_min      2.0970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             650
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
11 -3 -11 0.1830
12 5 12 0.1467
1 7 21 0.1166
-14 -3 -7 0.1390
0 -7 -21 0.1184
10 -4 -13 0.1745
5 12 -8 0.1234
-5 12 5 0.1668
-9 -7 12 0.1013
0 -13 1 0.0676
0 0 -21 0.1190
-9 4 -12 0.1421
2 14 11 0.1216
11 12 2 0.1490
8 13 12 0.1407

_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.219
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
11.0998 -3.3280 -10.7033 0.1207 -0.0021 0.9927
12.1882 4.5752 11.8483 0.9513 -0.0240 0.3074
1.4321 7.3576 20.9510 0.7902 -0.0208 -0.6124
-13.5155 -2.8415 -6.7377 -0.8328 0.0207 -0.5531
-0.4791 -7.3046 -20.8984 -0.7462 0.0198 0.6655
10.0608 -3.9626 -12.8324 0.0009 -0.0091 1.0000
5.1947 11.6332 -7.6854 -0.0248 -0.9791 0.2017
-4.5177 12.0554 4.9662 -0.0194 -0.7279 -0.6854
-9.0028 -6.9689 12.2974 0.0186 0.7572 -0.6529
-0.2619 -13.3514 1.3762 0.0249 0.9587 0.2835
-0.0136 0.1300 -20.9129 -0.7200 -0.4961 0.5079
-9.0625 3.9829 -11.8639 -0.8064 -0.5660 -0.3377
1.8713 13.9379 11.1704 0.4786 -0.7049 -0.5112
10.9002 12.0830 2.1530 0.5668 -0.7730 0.2826
7.8918 12.9910 12.1350 0.7777 -0.6079 -0.1599

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23449
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.050
_diffrn_reflns_theta_min         2.104
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.827
_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  66.00   0.50    1.21    --   -8.66  57.00  30.00  194
  2  ω     -1.00  24.00   0.50    1.21    --    9.13 -57.00  90.00   50
  3  ω    -25.00   6.00   0.50    1.21    --   -8.66 -81.00 -26.00   62
  4  ω    -29.00  41.00   0.50    1.21    --   -8.66  81.00  95.00  140
  5  ω    -33.00   2.00   0.50    1.21    --    9.13 109.00 -20.11   70
  6  ω    -41.00 -15.00   0.50    1.21    --    9.13 -57.00  90.00   52
  7  ω    -83.00 -45.00   0.50    1.21    --   -8.66 -81.00 -26.00   76
  8  ω    -26.00  49.00   0.50    1.21    --    9.13 -99.00 -30.00  150
  9  ω    -26.00  25.00   0.50    1.21    --   -8.66 -99.00-180.00  102
 10  ω    -16.00   9.00   0.50    1.21    --    9.13 -99.00-180.00   50
 11  ω    -25.00  46.00   0.50    1.21    --    9.13 -99.00-120.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0442975000
_diffrn_orient_matrix_UB_12      0.0008159000
_diffrn_orient_matrix_UB_13      0.0344042000
_diffrn_orient_matrix_UB_21      0.0014522000
_diffrn_orient_matrix_UB_22      -0.0694306000
_diffrn_orient_matrix_UB_23      0.0232892000
_diffrn_orient_matrix_UB_31      0.0583641000
_diffrn_orient_matrix_UB_32      -0.0248980000
_diffrn_orient_matrix_UB_33      -0.0244778000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5103
_reflns_number_total             7207
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.395
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         7207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      1.113
_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)+(0.0797P)²+1.0362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.1847
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C36(H36), C32(H32)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C30(H30), C29(H29), C26(H26), C17(H17), C8(H8), C5(H5), C18(H18),
 C21(H21), C6(H6), C7(H7), C20(H20), C19(H19), C15(H15), C11(H11), C13(H13),
 C14(H14), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.66235(7) 0.34160(7) 0.77342(4) 0.02754(18) Uani 1 1 d . . . . .
Cl34 Cl 0.69880(12) -0.04710(11) 0.96136(6) 0.0664(3) Uani 1 1 d . . . . .
Cl31 Cl 0.81244(12) -0.20962(14) 0.83635(8) 0.0784(3) Uani 1 1 d . . . . .
Cl38 Cl 1.18145(12) 0.14977(13) 0.68386(8) 0.0787(3) Uani 1 1 d . . . . .
Cl35 Cl 1.04847(12) -0.05591(13) 0.68056(10) 0.0833(4) Uani 1 1 d . . . . .
Cl33 Cl 0.51989(13) -0.08119(14) 0.83244(10) 0.0918(4) Uani 1 1 d . . . . .
Cl37 Cl 1.11561(14) -0.01884(15) 0.85293(9) 0.0935(4) Uani 1 1 d . . . . .
O22 O 0.7470(2) 0.20426(19) 0.76319(13) 0.0342(4) Uani 1 1 d . . . . .
C28 C 0.9694(2) 0.6575(2) 0.54338(16) 0.0245(5) Uani 1 1 d . . . . .
C27 C 0.9555(2) 0.5319(2) 0.53022(16) 0.0234(5) Uani 1 1 d . . . . .
C24 C 0.8529(2) 0.4716(2) 0.57599(16) 0.0244(5) Uani 1 1 d . . . . .
C25 C 1.1587(3) 0.6544(3) 0.44023(17) 0.0265(5) Uani 1 1 d . . . . .
H25 H 1.226422 0.694142 0.411522 0.032 Uiso 1 1 calc R . . . .
C23 C 0.7635(3) 0.5404(3) 0.63239(16) 0.0258(5) Uani 1 1 d . . . . .
C30 C 0.7798(3) 0.6618(3) 0.64530(17) 0.0298(5) Uani 1 1 d . . . . .
H30 H 0.721380 0.705094 0.683753 0.036 Uiso 1 1 calc R . . . .
C29 C 0.8806(3) 0.7195(3) 0.60240(17) 0.0297(5) Uani 1 1 d . . . . .
H29 H 0.889885 0.800458 0.612708 0.036 Uiso 1 1 calc R . . . .
C4 C 0.4133(3) 0.4907(3) 0.70981(17) 0.0290(5) Uani 1 1 d . . . . .
C26 C 1.0733(3) 0.7162(3) 0.49614(17) 0.0278(5) Uani 1 1 d . . . . .
H26 H 1.082145 0.798624 0.504188 0.033 Uiso 1 1 calc R . . . .
C3 C 0.5124(3) 0.5561(3) 0.65205(17) 0.0266(5) Uani 1 1 d . . . . .
C16 C 0.4663(3) 0.6827(3) 0.57439(17) 0.0284(5) Uani 1 1 d . . . . .
C2 C 0.6462(3) 0.4898(3) 0.67536(16) 0.0261(5) Uani 1 1 d . . . . .
C9 C 0.4781(3) 0.3727(3) 0.77953(17) 0.0294(5) Uani 1 1 d . . . . .
C10 C 0.7235(3) 0.3818(3) 0.86837(17) 0.0322(6) Uani 1 1 d . . . . .
C17 C 0.5150(3) 0.6819(3) 0.48775(17) 0.0299(5) Uani 1 1 d . . . . .
H17 H 0.573981 0.600926 0.478290 0.036 Uiso 1 1 calc R . . . .
C8 C 0.4015(3) 0.2976(3) 0.83827(18) 0.0348(6) Uani 1 1 d . . . . .
H8 H 0.445147 0.219651 0.884599 0.042 Uiso 1 1 calc R . . . .
C5 C 0.2705(3) 0.5329(3) 0.69951(19) 0.0359(6) Uani 1 1 d . . . . .
H5 H 0.226368 0.611605 0.653852 0.043 Uiso 1 1 calc R . . . .
C18 C 0.4762(3) 0.8010(3) 0.41588(19) 0.0370(6) Uani 1 1 d . . . . .
H18 H 0.508733 0.799461 0.358313 0.044 Uiso 1 1 calc R . . . .
C21 C 0.3784(3) 0.8053(3) 0.5868(2) 0.0376(6) Uani 1 1 d . . . . .
H21 H 0.344559 0.807260 0.644049 0.045 Uiso 1 1 calc R . . . .
C6 C 0.1941(3) 0.4561(3) 0.7583(2) 0.0407(7) Uani 1 1 d . . . . .
H6 H 0.098300 0.483259 0.751206 0.049 Uiso 1 1 calc R . . . .
C7 C 0.2584(3) 0.3402(3) 0.8271(2) 0.0399(7) Uani 1 1 d . . . . .
H7 H 0.205777 0.290499 0.866190 0.048 Uiso 1 1 calc R . . . .
C20 C 0.3410(3) 0.9241(3) 0.5148(2) 0.0457(7) Uani 1 1 d . . . . .
H20 H 0.283078 1.005822 0.523927 0.055 Uiso 1 1 calc R . . . .
C19 C 0.3896(3) 0.9217(3) 0.4291(2) 0.0430(7) Uani 1 1 d . . . . .
H19 H 0.363745 1.001476 0.380649 0.052 Uiso 1 1 calc R . . . .
C15 C 0.6457(4) 0.4854(4) 0.9036(3) 0.0576(9) Uani 1 1 d . . . . .
H15 H 0.558942 0.538429 0.877848 0.069 Uiso 1 1 calc R . . . .
C36 C 1.0632(4) 0.0620(4) 0.7390(3) 0.0549(9) Uani 1 1 d . . . . .
H36 H 0.972867 0.130123 0.736592 0.066 Uiso 1 1 calc R . . . .
C11 C 0.8537(4) 0.3059(4) 0.9051(3) 0.0597(10) Uani 1 1 d . . . . .
H11 H 0.906840 0.235593 0.881404 0.072 Uiso 1 1 calc R . . . .
C32 C 0.6839(4) -0.0666(4) 0.8525(2) 0.0547(9) Uani 1 1 d . . . . .
H32 H 0.695646 0.017024 0.808028 0.066 Uiso 1 1 calc R . . . .
C13 C 0.8275(4) 0.4334(5) 1.0149(3) 0.0634(10) Uani 1 1 d . . . . .
H13 H 0.861373 0.449240 1.065274 0.076 Uiso 1 1 calc R . . . .
C14 C 0.6974(5) 0.5107(5) 0.9781(3) 0.0726(12) Uani 1 1 d . . . . .
H14 H 0.644385 0.579648 1.002988 0.087 Uiso 1 1 calc R . . . .
C12 C 0.9051(4) 0.3355(5) 0.9782(3) 0.0743(13) Uani 1 1 d . . . . .
H12 H 0.994138 0.286788 1.001631 0.089 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 O22 1.4924(19) . ?
P1 C2 1.807(3) . ?
P1 C9 1.798(3) . ?
P1 C10 1.798(3) . ?
Cl34 C32 1.753(4) . ?
Cl31 C32 1.748(4) . ?
Cl38 C36 1.754(4) . ?
Cl35 C36 1.749(4) . ?
Cl33 C32 1.752(4) . ?
Cl37 C36 1.747(4) . ?
C28 C27 1.424(3) . ?
C28 C29 1.401(4) . ?
C28 C26 1.431(3) . ?
C27 C27 1.427(5) 2_766 ?
C27 C24 1.421(3) . ?
C24 C25 1.440(3) 2_766 ?
C24 C23 1.408(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.348(4) . ?
C23 C30 1.388(4) . ?
C23 C2 1.484(3) . ?
C30 H30 0.9300 . ?
C30 C29 1.377(4) . ?
C29 H29 0.9300 . ?
C4 C3 1.490(3) . ?
C4 C9 1.402(4) . ?
C4 C5 1.386(4) . ?
C26 H26 0.9300 . ?
C3 C16 1.486(3) . ?
C3 C2 1.345(4) . ?
C16 C17 1.396(4) . ?
C16 C21 1.391(4) . ?
C9 C8 1.382(4) . ?
C10 C15 1.371(4) . ?
C10 C11 1.380(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.390(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.383(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(4) . ?
C7 H7 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.385(5) . ?
C19 H19 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.393(5) . ?
C36 H36 0.9800 . ?
C11 H11 0.9300 . ?
C11 C12 1.396(5) . ?
C32 H32 0.9800 . ?
C13 H13 0.9300 . ?
C13 C14 1.383(6) . ?
C13 C12 1.341(6) . ?
C14 H14 0.9300 . ?
C12 H12 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
O22 P1 C2 116.56(11) . . ?
O22 P1 C9 118.33(12) . . ?
O22 P1 C10 111.69(12) . . ?
C9 P1 C2 92.36(12) . . ?
C10 P1 C2 107.79(12) . . ?
C10 P1 C9 108.29(12) . . ?
C27 C28 C26 119.1(2) . . ?
C29 C28 C27 118.7(2) . . ?
C29 C28 C26 122.2(2) . . ?
C28 C27 C27 119.4(3) . 2_766 ?
C24 C27 C28 120.3(2) . . ?
C24 C27 C27 120.4(3) . 2_766 ?
C27 C24 C25 118.4(2) . 2_766 ?
C23 C24 C27 118.8(2) . . ?
C23 C24 C25 122.8(2) . 2_766 ?
C24 C25 H25 119.3 2_766 . ?
C26 C25 C24 121.4(2) . 2_766 ?
C26 C25 H25 119.3 . . ?
C24 C23 C2 121.3(2) . . ?
C30 C23 C24 120.1(2) . . ?
C30 C23 C2 118.5(2) . . ?
C23 C30 H30 119.3 . . ?
C29 C30 C23 121.4(2) . . ?
C29 C30 H30 119.3 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.6(2) . . ?
C30 C29 H29 119.7 . . ?
C9 C4 C3 113.3(2) . . ?
C5 C4 C3 127.0(2) . . ?
C5 C4 C9 119.6(2) . . ?
C28 C26 H26 119.3 . . ?
C25 C26 C28 121.4(2) . . ?
C25 C26 H26 119.3 . . ?
C16 C3 C4 122.4(2) . . ?
C2 C3 C4 114.4(2) . . ?
C2 C3 C16 123.2(2) . . ?
C17 C16 C3 120.2(2) . . ?
C21 C16 C3 121.1(2) . . ?
C21 C16 C17 118.7(2) . . ?
C23 C2 P1 124.73(18) . . ?
C3 C2 P1 110.64(19) . . ?
C3 C2 C23 124.3(2) . . ?
C4 C9 P1 109.27(19) . . ?
C8 C9 P1 129.8(2) . . ?
C8 C9 C4 120.9(3) . . ?
C15 C10 P1 122.0(2) . . ?
C15 C10 C11 120.0(3) . . ?
C11 C10 P1 118.0(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C9 C8 H8 120.5 . . ?
C9 C8 C7 119.1(3) . . ?
C7 C8 H8 120.5 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(3) . . ?
C6 C5 H5 120.4 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.5(3) . . ?
C20 C21 H21 119.7 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.5 . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C21 C20 H20 119.9 . . ?
C21 C20 C19 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C10 C15 H15 120.2 . . ?
C10 C15 C14 119.6(4) . . ?
C14 C15 H15 120.2 . . ?
Cl38 C36 H36 108.5 . . ?
Cl35 C36 Cl38 108.6(2) . . ?
Cl35 C36 H36 108.5 . . ?
Cl37 C36 Cl38 110.1(2) . . ?
Cl37 C36 Cl35 112.5(2) . . ?
Cl37 C36 H36 108.5 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
Cl34 C32 H32 107.9 . . ?
Cl31 C32 Cl34 111.4(2) . . ?
Cl31 C32 Cl33 110.41(19) . . ?
Cl31 C32 H32 107.9 . . ?
Cl33 C32 Cl34 111.1(2) . . ?
Cl33 C32 H32 107.9 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 119.9(4) . . ?
C13 C14 H14 120.0 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.769
####################################################################### 
# 
# 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_201205_saito_1
_database_code_depnum_ccdc_archive 'CCDC 2174057'
loop_
_audit_author_name
_audit_author_address
'Shibo Xu'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-21 deposited with the CCDC.	2022-09-06 downloaded from the CCDC.
;
_audit_creation_date             2020-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 O P'
_chemical_formula_sum            'C22 H19 O P'
_chemical_formula_weight         330.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H19 P O'
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                   12.5743(3)
_cell_length_b                   11.3680(2)
_cell_length_c                   11.7601(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.369(2)
_cell_angle_gamma                90
_cell_volume                     1678.14(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6381
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      73.4350
_cell_measurement_theta_min      3.4870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.472
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -8 0.1860
7 -4 0 0.0551
0 0 8 0.2018
-7 4 0 0.0511
5 6 0 0.0278
-5 -6 0 0.0482
2 7 -3 0.0766
1 -6 4 0.1360
-5 3 5 0.1411

_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.079
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.2230 -0.1655 -7.6284 0.7326 -0.0189 0.6804
6.5401 -4.3949 0.0579 0.6658 -0.0173 -0.7459
-0.2935 0.2130 7.6289 -0.7399 0.0191 -0.6725
-6.5462 4.3993 0.1096 -0.6820 0.0178 0.7311
5.2095 5.6686 0.1084 -0.0259 -0.9968 -0.0755
-5.0876 -5.7662 0.0360 0.0259 0.9985 0.0474
1.7124 6.6727 -2.9256 -0.0221 -0.8511 0.5245
0.6224 -6.1123 4.1934 0.0161 0.6199 -0.7845
-4.9505 3.3376 5.2541 -0.9969 0.0259 0.0745

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13235
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.194
_diffrn_reflns_theta_min         3.521
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00 -22.00   0.50    0.05    --  -42.93  89.00 118.00   50
  2  ω    -96.00 -23.00   0.50    0.05    --  -42.93 125.00  90.00  146
  3  ω    -76.00 -35.00   0.50    0.05    -- -106.00 125.00 -30.00   82
  4  ω    -85.00 -59.00   0.50    0.05    -- -106.00 125.00-120.00   52
  5  ω   -128.00 -28.00   0.50    0.05    -- -106.00  37.00-180.00  200
  6  ω    -85.00 -26.00   0.50    0.05    -- -106.00  19.00-150.00  118
  7  ω    -63.00 -26.00   0.50    0.05    -- -106.00  19.00 -60.00   74
  8  ω   -108.00 -83.00   0.50    0.05    -- -106.00 -57.00  30.00   50
  9  ω   -127.00-102.00   0.50    0.05    -- -106.00 -89.00   2.00   50
 10  ω   -130.00 -84.00   0.50    0.05    -- -106.00 -99.00  60.00   92
 11  ω   -115.00 -70.00   0.50    0.05    --  -42.93-125.00  60.00   90
 12  ω   -115.00 -84.00   0.50    0.05    --  -42.93-125.00 -30.00   62
 13  ω    -30.00  58.00   0.50    0.05    --   42.93 -89.00   2.00  176
 14  ω     32.00  57.00   0.50    0.05    --   76.50 -89.00   2.00   50
 15  ω     89.00 114.00   0.50    0.05    --   76.50  89.00 118.00   50
 16  ω     72.00 117.00   0.50    0.05    --   42.93 125.00  30.00   90
 17  ω     80.00 115.00   0.50    0.05    --   42.93 125.00-150.00   70
 18  ω    -95.00 -69.00   0.50    0.05    -- -106.00  77.00 150.00   52
 19  ω   -118.00 -61.00   0.50    0.05    -- -106.00  89.00 118.00  114
 20  ω   -126.00 -28.00   0.50    0.05    -- -106.00  37.00  30.00  196
 21  ω   -131.00-106.00   0.50    0.05    -- -106.00  77.00 150.00   50
 22  ω   -129.00 -50.00   0.50    0.05    -- -106.00  77.00  90.00  158
 23  ω   -132.00-107.00   0.50    0.05    -- -106.00  19.00 -60.00   50
 24  ω   -114.00 -40.00   0.50    0.05    -- -106.00  77.00-120.00  148
 25  ω   -135.00-106.00   0.50    0.05    -- -106.00  19.00-150.00   58
 26  ω   -170.00-144.00   0.50    0.05    -- -106.00 -57.00  30.00   52
 27  ω   -170.00-135.00   0.50    0.05    -- -106.00 -37.00  60.00   70
 28  ω   -173.00-133.00   0.50    0.05    -- -106.00 -99.00  60.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0622882000
_diffrn_orient_matrix_UB_12      -0.0600299000
_diffrn_orient_matrix_UB_13      -0.0929116000
_diffrn_orient_matrix_UB_21      -0.0747269000
_diffrn_orient_matrix_UB_22      -0.1072222000
_diffrn_orient_matrix_UB_23      0.0026264000
_diffrn_orient_matrix_UB_31      -0.0747993000
_diffrn_orient_matrix_UB_32      0.0571935000
_diffrn_orient_matrix_UB_33      -0.0926215000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3075
_reflns_number_total             3366
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_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         0.344
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.064
_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)+(0.0543P)²+0.7919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1094
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C15(H15), C18(H18), C17(H17), C20(H20), C5(H5), C2(H2),
 C6(H6), C13(H13), C21(H21), C14(H14), C12(H12)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.80990(3) 0.20539(3) 0.33843(3) 0.01734(13) Uani 1 1 d . . . . .
O23 O 0.82526(9) 0.10314(10) 0.41643(10) 0.0236(3) Uani 1 1 d . . . . .
C8 C 0.82075(12) 0.40727(13) 0.48770(12) 0.0188(3) Uani 1 1 d . . . . .
H8 H 0.884338 0.380221 0.522750 0.023 Uiso 1 1 calc R . . . .
C16 C 0.54539(12) 0.33229(14) 0.16761(13) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.92486(12) 0.22857(14) 0.25616(12) 0.0178(3) Uani 1 1 d . . . . .
C4 C 0.67615(12) 0.38436(14) 0.34206(12) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.77130(12) 0.34451(13) 0.39903(13) 0.0181(3) Uani 1 1 d . . . . .
C11 C 0.93113(13) 0.32125(14) 0.17886(14) 0.0218(3) Uani 1 1 d . . . . .
H11 H 0.876558 0.376436 0.171551 0.026 Uiso 1 1 calc R . . . .
C3 C 0.63685(12) 0.30409(14) 0.24785(13) 0.0189(3) Uani 1 1 d . . . . .
C15 C 1.00622(12) 0.14516(14) 0.26544(13) 0.0209(3) Uani 1 1 d . . . . .
H15 H 1.002568 0.083516 0.317058 0.025 Uiso 1 1 calc R . . . .
C7 C 0.77480(13) 0.51206(14) 0.52485(13) 0.0208(3) Uani 1 1 d . . . . .
C19 C 0.37636(12) 0.38397(13) 0.00623(13) 0.0200(3) Uani 1 1 d . . . . .
C18 C 0.36412(12) 0.39691(14) 0.12278(14) 0.0214(3) Uani 1 1 d . . . . .
H18 H 0.299272 0.422875 0.147570 0.026 Uiso 1 1 calc R . . . .
C17 C 0.44690(12) 0.37176(14) 0.20239(13) 0.0212(3) Uani 1 1 d . . . . .
H17 H 0.436868 0.381208 0.279578 0.025 Uiso 1 1 calc R . . . .
C20 C 0.47455(13) 0.34422(14) -0.02823(13) 0.0223(3) Uani 1 1 d . . . . .
H20 H 0.484401 0.334583 -0.105431 0.027 Uiso 1 1 calc R . . . .
C5 C 0.63197(12) 0.48949(14) 0.37670(13) 0.0211(3) Uani 1 1 d . . . . .
H5 H 0.570255 0.518549 0.339287 0.025 Uiso 1 1 calc R . . . .
C2 C 0.69651(12) 0.20648(14) 0.23845(13) 0.0200(3) Uani 1 1 d . . . . .
H2 H 0.680737 0.146648 0.186212 0.024 Uiso 1 1 calc R . . . .
C6 C 0.68103(12) 0.55130(14) 0.46830(13) 0.0222(3) Uani 1 1 d . . . . .
H6 H 0.650103 0.620692 0.492146 0.027 Uiso 1 1 calc R . . . .
C13 C 1.09926(13) 0.24669(16) 0.12252(14) 0.0251(4) Uani 1 1 d . . . . .
H13 H 1.157732 0.252837 0.077999 0.030 Uiso 1 1 calc R . . . .
C21 C 0.55739(13) 0.31894(15) 0.05067(14) 0.0221(3) Uani 1 1 d . . . . .
H21 H 0.622045 0.292678 0.025647 0.026 Uiso 1 1 calc R . . . .
C14 C 1.09275(13) 0.15401(15) 0.19769(14) 0.0242(3) Uani 1 1 d . . . . .
H14 H 1.146294 0.097505 0.202966 0.029 Uiso 1 1 calc R . . . .
C22 C 0.28707(13) 0.41288(15) -0.08023(14) 0.0251(3) Uani 1 1 d . . . . .
H22A H 0.233027 0.353357 -0.078616 0.038 Uiso 1 1 calc GR . . . .
H22B H 0.314227 0.415881 -0.154787 0.038 Uiso 1 1 calc GR . . . .
H22C H 0.257055 0.487827 -0.062415 0.038 Uiso 1 1 calc GR . . . .
C12 C 1.01882(14) 0.33110(15) 0.11288(14) 0.0251(4) Uani 1 1 d . . . . .
H12 H 1.023821 0.393684 0.062551 0.030 Uiso 1 1 calc R . . . .
C24 C 0.82684(14) 0.57950(15) 0.62341(14) 0.0268(4) Uani 1 1 d . . . . .
H24A H 0.831876 0.530197 0.689785 0.040 Uiso 1 1 calc GR . . . .
H24B H 0.784870 0.647710 0.638365 0.040 Uiso 1 1 calc GR . . . .
H24C H 0.896927 0.603559 0.604879 0.040 Uiso 1 1 calc GR . . . .


_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 O23 1.4863(11) . ?
P1 C10 1.8054(15) . ?
P1 C9 1.8125(16) . ?
P1 C2 1.7940(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(2) . ?
C8 C7 1.405(2) . ?
C16 C3 1.479(2) . ?
C16 C17 1.401(2) . ?
C16 C21 1.400(2) . ?
C10 C11 1.397(2) . ?
C10 C15 1.394(2) . ?
C4 C9 1.411(2) . ?
C4 C3 1.497(2) . ?
C4 C5 1.389(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(2) . ?
C3 C2 1.348(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.390(2) . ?
C7 C6 1.393(2) . ?
C7 C24 1.507(2) . ?
C19 C18 1.396(2) . ?
C19 C20 1.397(2) . ?
C19 C22 1.506(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.388(2) . ?
C17 H17 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.384(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(2) . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.381(3) . ?
C13 C12 1.394(3) . ?
C21 H21 0.9300 . ?
C14 H14 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C12 H12 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
O23 P1 C10 111.45(7) . . ?
O23 P1 C9 117.89(7) . . ?
O23 P1 C2 118.64(7) . . ?
C10 P1 C9 108.95(7) . . ?
C2 P1 C10 106.16(7) . . ?
C2 P1 C9 91.77(7) . . ?
C9 C8 H8 120.1 . . ?
C9 C8 C7 119.85(14) . . ?
C7 C8 H8 120.1 . . ?
C17 C16 C3 123.41(14) . . ?
C21 C16 C3 118.58(14) . . ?
C21 C16 C17 118.01(14) . . ?
C11 C10 P1 122.44(12) . . ?
C15 C10 P1 117.75(12) . . ?
C15 C10 C11 119.65(14) . . ?
C9 C4 C3 112.93(13) . . ?
C5 C4 C9 118.65(14) . . ?
C5 C4 C3 128.41(14) . . ?
C8 C9 P1 128.95(12) . . ?
C8 C9 C4 121.62(14) . . ?
C4 C9 P1 109.43(11) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.08(15) . . ?
C12 C11 H11 120.0 . . ?
C16 C3 C4 123.41(14) . . ?
C2 C3 C16 122.80(14) . . ?
C2 C3 C4 113.68(14) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 120.10(15) . . ?
C14 C15 H15 120.0 . . ?
C8 C7 C24 120.18(15) . . ?
C6 C7 C8 118.38(14) . . ?
C6 C7 C24 121.44(15) . . ?
C18 C19 C20 117.99(14) . . ?
C18 C19 C22 121.27(14) . . ?
C20 C19 C22 120.74(14) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 C19 121.25(14) . . ?
C17 C18 H18 119.4 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.65(14) . . ?
C18 C17 H17 119.7 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.06(14) . . ?
C21 C20 H20 119.5 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.49(15) . . ?
C6 C5 H5 120.3 . . ?
P1 C2 H2 123.9 . . ?
C3 C2 P1 112.13(12) . . ?
C3 C2 H2 123.9 . . ?
C7 C6 C5 121.97(15) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.48(15) . . ?
C12 C13 H13 119.8 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 121.04(14) . . ?
C20 C21 H21 119.5 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.02(15) . . ?
C13 C14 H14 120.0 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C12 C13 119.66(15) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C7 C24 H24A 109.5 . . ?
C7 C24 H24B 109.5 . . ?
C7 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_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 1.518
_oxdiff_exptl_absorpt_empirical_full_min 0.633
