# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_SS601
_audit_block_doi                 10.5517/ccdc.csd.cc2lq5n5
_database_code_depnum_ccdc_archive 'CCDC 2404597'
loop_
_audit_author_name
_audit_author_address
'Kenta Kato'
;Waseda University
Japan
;
_audit_update_record             
;
2024-11-22 deposited with the CCDC.	2025-06-20 downloaded from the CCDC.
;
_audit_creation_date             2024-11-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 F2 O2 P'
_chemical_formula_sum            'C24 H23 F2 O2 P'
_chemical_formula_weight         412.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N 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'
F F 0.0727 0.0534 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.24160(10)
_cell_length_b                   14.70540(10)
_cell_length_c                   22.9539(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4132.11(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16689
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      75.0690
_cell_measurement_theta_min      3.0270
_shelx_estimated_absorpt_T_max   0.648
_shelx_estimated_absorpt_T_min   0.519
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.213
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -9 -3 0.2486
2 -2 14 0.1492
1 9 -1 0.2090
-2 1 -14 0.1511
7 -3 2 0.1506
4 8 2 0.2359
-3 9 0 0.2395
-8 -1 -2 0.0999
0 -9 -3 0.2599
5 -2 -12 0.2744
2 9 0 0.2120
-5 0 12 0.0821

_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.32
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
-1.4442 -9.1468 -3.3322 -0.0450 -0.1726 0.9840
1.8702 -2.2639 14.0394 0.2286 0.9614 0.1532
0.7682 9.4616 -1.3957 -0.0315 -0.1486 -0.9884
-2.0310 1.0882 -14.3022 -0.2317 -0.9724 -0.0277
7.4052 -3.2070 1.9795 0.9627 0.1808 0.2011
4.2818 7.9825 1.6004 0.4194 0.0747 -0.9047
-2.9504 8.8578 -0.4374 -0.4893 -0.0950 -0.8669
-7.7981 -1.0882 -2.2915 -0.9515 -0.1769 0.2517
-0.0534 -9.3504 -3.0316 0.1305 -0.1459 0.9807
4.7744 -1.5269 -11.6668 0.6464 -0.7536 0.1198
1.5511 9.3614 -0.4629 0.0651 -0.0825 -0.9945
-4.9838 -0.1209 11.5997 -0.6495 0.7584 0.0548

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23326
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.381
_diffrn_reflns_theta_min         3.852
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     55.00  98.00   0.50    0.15    --  108.78 -77.00-150.00   86
  2  ω     67.00 111.00   0.50    0.15    --  108.78-125.00  30.00   88
  3  ω     37.00  96.00   0.50    0.15    --  108.78-128.00  54.00  118
  4  ω     64.00 105.00   0.50    0.15    --  108.78 -95.00  60.00   82
  5  ω     39.00  97.00   0.50    0.15    --  108.78 -77.00  60.00  116
  6  ω     87.00 154.00   0.50    0.15    --  108.78  45.00  60.00  134
  7  ω    -28.00  38.00   0.50    0.05    --  -42.85  19.00 -30.00  132
  8  ω    -26.00  38.00   0.50    0.05    --  -42.85  19.00 -90.00  128
  9  ω    -28.00  38.00   0.50    0.05    --  -42.85  19.00  30.00  132
 10  ω    -51.00 -21.00   0.50    0.15    --  -96.00  45.00 -90.00   60
 11  ω    -46.00 -21.00   0.50    0.15    --  -96.00  45.00   0.00   50
 12  ω    -49.00 -20.00   0.50    0.15    --  -96.00  45.00  60.00   58
 13  ω    -69.00 -27.00   0.50    0.15    --  -96.00  61.00 150.00   84
 14  ω    -72.00 -29.00   0.50    0.15    --  -96.00 119.00  44.00   86
 15  ω    -80.00 -46.00   0.50    0.15    --  -96.00 128.00 129.00   68
 16  ω    -99.00 -56.00   0.50    0.05    --  -42.85 143.00 -60.00   86
 17  ω   -107.00 -41.00   0.50    0.15    --  -96.00 -11.00 117.00  132
 18  ω   -176.00-129.00   0.50    0.15    --  -96.00 -11.00 117.00   94
 19  ω   -143.00 -71.00   0.50    0.15    --  -96.00 -77.00 150.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1247004000
_diffrn_orient_matrix_UB_12      -0.0138349000
_diffrn_orient_matrix_UB_13      -0.0025602000
_diffrn_orient_matrix_UB_21      0.0038592000
_diffrn_orient_matrix_UB_22      -0.0061366000
_diffrn_orient_matrix_UB_23      0.0669741000
_diffrn_orient_matrix_UB_31      -0.0167673000
_diffrn_orient_matrix_UB_32      -0.1036289000
_diffrn_orient_matrix_UB_33      -0.0035632000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3890
_reflns_number_total             4115
_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 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.051
_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)+(0.0383P)²+1.9888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0822
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C14(H14), C5(H5), C7(H7), C18(H18), C20(H20), C16(H16),
 C17(H17), C24(H24), C15(H15), C21(H21), C23(H23), C22(H22)
1.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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 0.15718(2) 0.62531(2) 0.61635(2) 0.01566(9) Uani 1 1 d . . . . .
F1 F 0.16418(6) 0.32973(5) 0.69709(3) 0.02570(18) Uani 1 1 d . . . . .
F2 F 0.03085(6) 0.40632(5) 0.65933(4) 0.02808(18) Uani 1 1 d . . . . .
O2 O 0.16148(7) 0.51816(6) 0.59972(4) 0.01843(18) Uani 1 1 d . . . . .
O1 O 0.26400(7) 0.67092(6) 0.61983(4) 0.02148(19) Uani 1 1 d . . . . .
C3 C 0.32848(10) 0.44258(8) 0.63463(5) 0.0171(2) Uani 1 1 d . . . . .
C4 C 0.38745(10) 0.48113(8) 0.58879(5) 0.0192(2) Uani 1 1 d . . . . .
H4 H 0.350561 0.517307 0.560712 0.023 Uiso 1 1 calc R U . . .
C13 C 0.08392(10) 0.63099(7) 0.68410(5) 0.0166(2) Uani 1 1 d . . . . .
C8 C 0.38638(10) 0.39195(8) 0.67600(5) 0.0201(2) Uani 1 1 d . . . . .
H8 H 0.348854 0.366470 0.708340 0.024 Uiso 1 1 calc R U . . .
C19 C 0.07297(10) 0.66301(8) 0.55728(5) 0.0191(2) Uani 1 1 d . . . . .
C14 C 0.13616(10) 0.66900(8) 0.73221(5) 0.0206(2) Uani 1 1 d . . . . .
H14 H 0.208484 0.691753 0.728635 0.025 Uiso 1 1 calc R U . . .
C5 C 0.49919(10) 0.46735(8) 0.58367(5) 0.0192(2) Uani 1 1 d . . . . .
H5 H 0.537142 0.494213 0.551938 0.023 Uiso 1 1 calc R U . . .
C7 C 0.49784(10) 0.37865(8) 0.67025(5) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.535136 0.343592 0.698765 0.024 Uiso 1 1 calc R U . . .
C2 C 0.20888(10) 0.45329(8) 0.63645(5) 0.0176(2) Uani 1 1 d . . . . .
C18 C -0.02279(10) 0.59880(8) 0.68977(6) 0.0215(3) Uani 1 1 d . . . . .
H18 H -0.059487 0.573983 0.656955 0.026 Uiso 1 1 calc R U . . .
C6 C 0.55721(10) 0.41524(8) 0.62376(5) 0.0179(2) Uani 1 1 d . . . . .
C20 C -0.01355(11) 0.61118(9) 0.53549(6) 0.0231(3) Uani 1 1 d . . . . .
H20 H -0.028680 0.553000 0.551560 0.028 Uiso 1 1 calc R U . . .
C1 C 0.13844(10) 0.39925(8) 0.66339(6) 0.0205(2) Uani 1 1 d . . . . .
C16 C -0.02299(12) 0.64048(9) 0.79103(6) 0.0263(3) Uani 1 1 d . . . . .
H16 H -0.059231 0.643497 0.827573 0.032 Uiso 1 1 calc R U . . .
C9 C 0.67989(10) 0.39682(9) 0.61867(5) 0.0212(3) Uani 1 1 d . . . . .
C17 C -0.07542(11) 0.60297(9) 0.74325(6) 0.0244(3) Uani 1 1 d . . . . .
H17 H -0.147609 0.580025 0.747109 0.029 Uiso 1 1 calc R U . . .
C24 C 0.09572(11) 0.74773(9) 0.53290(6) 0.0253(3) Uani 1 1 d . . . . .
H24 H 0.154444 0.783288 0.547500 0.030 Uiso 1 1 calc R U . . .
C15 C 0.08238(12) 0.67358(9) 0.78537(6) 0.0267(3) Uani 1 1 d . . . . .
H15 H 0.118126 0.699596 0.818111 0.032 Uiso 1 1 calc R U . . .
C21 C -0.07743(12) 0.64471(10) 0.49035(6) 0.0304(3) Uani 1 1 d . . . . .
H21 H -0.136990 0.609857 0.476016 0.036 Uiso 1 1 calc R U . . .
C23 C 0.03230(14) 0.77998(10) 0.48723(6) 0.0329(3) Uani 1 1 d . . . . .
H23 H 0.048427 0.837386 0.470306 0.039 Uiso 1 1 calc R U . . .
C22 C -0.05440(13) 0.72906(10) 0.46611(6) 0.0344(3) Uani 1 1 d . . . . .
H22 H -0.097966 0.751847 0.435129 0.041 Uiso 1 1 calc R U . . .
C12 C 0.69991(12) 0.29374(10) 0.61902(7) 0.0347(3) Uani 1 1 d . . . . .
H12A H 0.677322 0.268513 0.656658 0.052 Uiso 1 1 calc R U . . .
H12B H 0.777785 0.281673 0.612850 0.052 Uiso 1 1 calc R U . . .
H12C H 0.657401 0.265257 0.587784 0.052 Uiso 1 1 calc R U . . .
C10 C 0.72875(12) 0.43404(11) 0.56199(7) 0.0336(3) Uani 1 1 d . . . . .
H10A H 0.692527 0.405423 0.528624 0.050 Uiso 1 1 calc R U . . .
H10B H 0.807099 0.420491 0.560781 0.050 Uiso 1 1 calc R U . . .
H10C H 0.717862 0.500017 0.560337 0.050 Uiso 1 1 calc R U . . .
C11 C 0.73815(12) 0.44137(13) 0.67013(7) 0.0383(4) Uani 1 1 d . . . . .
H11A H 0.726603 0.507282 0.668833 0.057 Uiso 1 1 calc R U . . .
H11B H 0.816551 0.428323 0.667920 0.057 Uiso 1 1 calc R U . . .
H11C H 0.708692 0.417082 0.706651 0.057 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 O2 1.6222(9) . ?
P1 O1 1.4718(9) . ?
P1 C13 1.7970(12) . ?
P1 C19 1.7912(12) . ?
F1 C1 1.3201(15) . ?
F2 C1 1.3244(15) . ?
O2 C2 1.3991(14) . ?
C3 C4 1.3962(17) . ?
C3 C8 1.3995(17) . ?
C3 C2 1.4731(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3878(18) . ?
C13 C14 1.3932(17) . ?
C13 C18 1.3955(17) . ?
C8 H8 0.9500 . ?
C8 C7 1.3847(18) . ?
C19 C20 1.3975(18) . ?
C19 C24 1.3939(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3883(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3923(17) . ?
C7 H7 0.9500 . ?
C7 C6 1.3988(17) . ?
C2 C1 1.3257(18) . ?
C18 H18 0.9500 . ?
C18 C17 1.3877(18) . ?
C6 C9 1.5305(17) . ?
C20 H20 0.9500 . ?
C20 C21 1.3885(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(2) . ?
C16 C15 1.385(2) . ?
C9 C12 1.5355(19) . ?
C9 C10 1.5330(18) . ?
C9 C11 1.5275(19) . ?
C17 H17 0.9500 . ?
C24 H24 0.9500 . ?
C24 C23 1.388(2) . ?
C15 H15 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.388(2) . ?
C23 H23 0.9500 . ?
C23 C22 1.386(2) . ?
C22 H22 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
O2 P1 C13 105.37(5) . . ?
O2 P1 C19 98.11(5) . . ?
O1 P1 O2 115.25(5) . . ?
O1 P1 C13 112.05(5) . . ?
O1 P1 C19 114.29(6) . . ?
C19 P1 C13 110.69(6) . . ?
C2 O2 P1 122.26(7) . . ?
C4 C3 C8 117.74(11) . . ?
C4 C3 C2 119.46(11) . . ?
C8 C3 C2 122.75(11) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.94(11) . . ?
C5 C4 H4 119.5 . . ?
C14 C13 P1 118.38(9) . . ?
C14 C13 C18 119.46(11) . . ?
C18 C13 P1 122.16(9) . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.64(11) . . ?
C7 C8 H8 119.7 . . ?
C20 C19 P1 122.58(10) . . ?
C24 C19 P1 117.75(10) . . ?
C24 C19 C20 119.67(12) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.91(12) . . ?
C15 C14 H14 120.0 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.81(11) . . ?
C6 C5 H5 119.1 . . ?
C8 C7 H7 119.0 . . ?
C8 C7 C6 122.03(11) . . ?
C6 C7 H7 119.0 . . ?
O2 C2 C3 117.90(10) . . ?
C1 C2 O2 114.84(11) . . ?
C1 C2 C3 126.56(11) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.15(12) . . ?
C17 C18 H18 119.9 . . ?
C5 C6 C7 116.80(11) . . ?
C5 C6 C9 123.19(11) . . ?
C7 C6 C9 120.00(11) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.02(13) . . ?
C21 C20 H20 120.0 . . ?
F1 C1 F2 109.83(10) . . ?
F1 C1 C2 125.61(11) . . ?
F2 C1 C2 124.54(12) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.83(12) . . ?
C6 C9 C12 109.33(11) . . ?
C6 C9 C10 112.61(11) . . ?
C10 C9 C12 107.14(12) . . ?
C11 C9 C6 108.86(11) . . ?
C11 C9 C12 110.17(12) . . ?
C11 C9 C10 108.72(12) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.18(12) . . ?
C16 C17 H17 119.9 . . ?
C19 C24 H24 120.1 . . ?
C23 C24 C19 119.79(13) . . ?
C23 C24 H24 120.1 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.47(12) . . ?
C16 C15 H15 119.8 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.12(14) . . ?
C22 C21 H21 119.9 . . ?
C24 C23 H23 119.7 . . ?
C22 C23 C24 120.51(13) . . ?
C22 C23 H23 119.7 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.86(13) . . ?
C23 C22 H22 120.1 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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 O2 C2 C3 -81.76(12) . . . . ?
P1 O2 C2 C1 107.22(11) . . . . ?
P1 C13 C14 C15 -179.31(10) . . . . ?
P1 C13 C18 C17 178.73(10) . . . . ?
P1 C19 C20 C21 178.73(10) . . . . ?
P1 C19 C24 C23 -179.68(10) . . . . ?
O2 P1 C13 C14 120.88(9) . . . . ?
O2 P1 C13 C18 -59.18(11) . . . . ?
O2 P1 C19 C20 37.10(11) . . . . ?
O2 P1 C19 C24 -143.19(10) . . . . ?
O2 C2 C1 F1 175.49(10) . . . . ?
O2 C2 C1 F2 -3.10(18) . . . . ?
O1 P1 O2 C2 65.41(10) . . . . ?
O1 P1 C13 C14 -5.17(11) . . . . ?
O1 P1 C13 C18 174.76(9) . . . . ?
O1 P1 C19 C20 159.59(10) . . . . ?
O1 P1 C19 C24 -20.71(12) . . . . ?
C3 C4 C5 C6 -0.26(19) . . . . ?
C3 C8 C7 C6 0.52(19) . . . . ?
C3 C2 C1 F1 5.4(2) . . . . ?
C3 C2 C1 F2 -173.21(11) . . . . ?
C4 C3 C8 C7 -1.94(18) . . . . ?
C4 C3 C2 O2 -13.98(16) . . . . ?
C4 C3 C2 C1 155.85(12) . . . . ?
C4 C5 C6 C7 -1.17(18) . . . . ?
C4 C5 C6 C9 178.53(11) . . . . ?
C13 P1 O2 C2 -58.65(10) . . . . ?
C13 P1 C19 C20 -72.77(11) . . . . ?
C13 P1 C19 C24 106.93(10) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C13 C18 C17 C16 1.09(19) . . . . ?
C8 C3 C4 C5 1.82(18) . . . . ?
C8 C3 C2 O2 168.57(11) . . . . ?
C8 C3 C2 C1 -21.59(19) . . . . ?
C8 C7 C6 C5 1.05(18) . . . . ?
C8 C7 C6 C9 -178.66(12) . . . . ?
C19 P1 O2 C2 -172.81(9) . . . . ?
C19 P1 C13 C14 -134.03(10) . . . . ?
C19 P1 C13 C18 45.90(11) . . . . ?
C19 C20 C21 C22 1.1(2) . . . . ?
C19 C24 C23 C22 0.8(2) . . . . ?
C14 C13 C18 C17 -1.34(18) . . . . ?
C5 C6 C9 C12 -124.48(13) . . . . ?
C5 C6 C9 C10 -5.51(18) . . . . ?
C5 C6 C9 C11 115.13(14) . . . . ?
C7 C6 C9 C12 55.21(15) . . . . ?
C7 C6 C9 C10 174.18(12) . . . . ?
C7 C6 C9 C11 -65.18(15) . . . . ?
C2 C3 C4 C5 -175.75(11) . . . . ?
C2 C3 C8 C7 175.55(11) . . . . ?
C18 C13 C14 C15 0.76(18) . . . . ?
C20 C19 C24 C23 0.03(19) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C17 C16 C15 C14 -0.3(2) . . . . ?
C24 C19 C20 C21 -0.96(19) . . . . ?
C24 C23 C22 C21 -0.7(2) . . . . ?
C15 C16 C17 C18 -0.2(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 1.595
_oxdiff_exptl_absorpt_empirical_full_min 0.792

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
