# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_678-1_2
_database_code_depnum_ccdc_archive 'CCDC 2223859'
loop_
_audit_author_name
_audit_author_address
cxq
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-12-02 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;
_audit_creation_date             2022-12-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H20 F O2 P'
_chemical_formula_sum            'C28 H20 F O2 P'
_chemical_formula_weight         438.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   12.9054(3)
_cell_length_b                   15.6356(3)
_cell_length_c                   11.0833(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.718(2)
_cell_angle_gamma                90
_cell_volume                     2152.80(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5619
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.4540
_cell_measurement_theta_min      2.7920
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    1.397
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8405
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.832
_diffrn_reflns_theta_min         3.558
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -23.00   1.00    1.50    --  -40.73 -38.00 -30.00   27
  2  ω    -34.00  66.00   1.00    1.50    --   40.73 -77.00 -60.00  100
  3  ω     35.00 132.00   1.00    3.00    --  107.58 -45.00 -60.00   97
  4  ω    124.00 149.00   1.00    3.00    --  107.58  45.00-180.00   25
  5  ω     94.00 150.00   1.00    3.00    --  107.58 125.00 -90.00   56
  6  ω     95.00 142.00   1.00    3.00    --  107.58 125.00   0.00   47
  7  ω     90.00 177.00   1.00    3.00    --  107.58  61.00  90.00   87
  8  ω     31.00 137.00   1.00    3.00    --  107.58 -77.00 -90.00  106
  9  ω    -65.00  19.00   1.00    1.50    --  -40.73  38.00 150.00   84
 10  ω   -111.00 -71.00   1.00    1.50    --  -40.73 -38.00 -30.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0170776000
_diffrn_orient_matrix_UB_12      0.0857283000
_diffrn_orient_matrix_UB_13      -0.0603405000
_diffrn_orient_matrix_UB_21      0.0963544000
_diffrn_orient_matrix_UB_22      -0.0386260000
_diffrn_orient_matrix_UB_23      -0.0382908000
_diffrn_orient_matrix_UB_31      -0.0761891000
_diffrn_orient_matrix_UB_32      -0.0294200000
_diffrn_orient_matrix_UB_33      -0.1254389000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3837
_reflns_number_total             4247
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.088
_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)+(0.0523P)²+1.1535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1130
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(F1B)=1-FVAR(1)
 Sof(F1)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24),
  C25(H25), C26(H26), C27(H27), C28(H28)
;
_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 0.76981(3) 0.69736(3) 0.35926(4) 0.01968(13) Uani 1 1 d . . . . .
F1 F 0.50719(11) 0.92805(9) 0.09906(13) 0.0337(4) Uani 0.801(3) 1 d . . P A 1
F1B F 0.6742(5) 0.9823(4) 0.1162(6) 0.0396(18) Uani 0.199(3) 1 d . . P A 2
O1 O 0.68240(11) 0.92318(9) 0.19238(13) 0.0329(3) Uani 1 1 d . . . . .
O2 O 0.75901(10) 0.68422(9) 0.48828(11) 0.0276(3) Uani 1 1 d . . . . .
C C 0.58715(13) 0.87996(12) 0.16520(17) 0.0249(4) Uani 1 1 d . . . . .
C1 C 0.50264(14) 0.74575(12) 0.21275(16) 0.0238(4) Uani 1 1 d . . . . .
C2 C 0.49915(15) 0.69183(13) 0.31181(18) 0.0291(4) Uani 1 1 d . . . . .
H2 H 0.556206 0.693092 0.386849 0.035 Uiso 1 1 calc R U . . .
C3 C 0.41328(15) 0.63634(14) 0.30209(18) 0.0317(4) Uani 1 1 d . . . . .
H3 H 0.412921 0.598945 0.369532 0.038 Uiso 1 1 calc R U . . .
C4 C 0.32796(15) 0.63521(13) 0.19431(19) 0.0309(4) Uani 1 1 d . . . . .
H4 H 0.269489 0.596930 0.187501 0.037 Uiso 1 1 calc R U . . .
C5 C 0.32878(15) 0.69030(13) 0.09693(19) 0.0313(4) Uani 1 1 d . . . . .
H5 H 0.269616 0.690946 0.023970 0.038 Uiso 1 1 calc R U . . .
C6 C 0.41550(14) 0.74465(13) 0.10507(17) 0.0279(4) Uani 1 1 d . . . . .
H6 H 0.415732 0.781461 0.036949 0.034 Uiso 1 1 calc R U . . .
C7 C 0.59470(14) 0.80312(12) 0.22018(16) 0.0244(4) Uani 1 1 d . . . . .
C9 C 0.70816(13) 0.79389(11) 0.28503(15) 0.0208(3) Uani 1 1 d . . . . .
C10 C 0.75765(14) 0.86945(11) 0.26573(16) 0.0224(3) Uani 1 1 d . . . . .
C11 C 0.86804(14) 0.90134(11) 0.30498(17) 0.0237(4) Uani 1 1 d . . . . .
C12 C 0.93361(15) 0.88373(12) 0.42446(17) 0.0263(4) Uani 1 1 d . . . . .
H12 H 0.905018 0.854617 0.483511 0.032 Uiso 1 1 calc R U . . .
C13 C 1.04074(16) 0.90872(13) 0.4572(2) 0.0336(4) Uani 1 1 d . . . . .
H13 H 1.085887 0.895516 0.538061 0.040 Uiso 1 1 calc R U . . .
C14 C 1.08203(16) 0.95283(14) 0.3724(2) 0.0382(5) Uani 1 1 d . . . . .
H14 H 1.155912 0.968485 0.394335 0.046 Uiso 1 1 calc R U . . .
C15 C 1.01596(17) 0.97418(14) 0.2557(2) 0.0371(5) Uani 1 1 d . . . . .
H15 H 1.043731 1.006494 0.198880 0.044 Uiso 1 1 calc R U . . .
C16 C 0.90922(16) 0.94839(13) 0.22173(19) 0.0304(4) Uani 1 1 d . . . . .
H16 H 0.863989 0.962849 0.141427 0.036 Uiso 1 1 calc R U . . .
C17 C 0.90920(13) 0.69477(11) 0.35656(16) 0.0207(3) Uani 1 1 d . . . . .
C18 C 0.98265(14) 0.66465(12) 0.46469(17) 0.0260(4) Uani 1 1 d . . . . .
H18 H 0.958742 0.649077 0.535547 0.031 Uiso 1 1 calc R U . . .
C19 C 1.09100(15) 0.65739(14) 0.46890(18) 0.0315(4) Uani 1 1 d . . . . .
H19 H 1.141062 0.636629 0.542490 0.038 Uiso 1 1 calc R U . . .
C20 C 1.12585(15) 0.68042(14) 0.36576(19) 0.0322(4) Uani 1 1 d . . . . .
H20 H 1.199998 0.676096 0.369084 0.039 Uiso 1 1 calc R U . . .
C21 C 1.05283(15) 0.70980(13) 0.25760(18) 0.0288(4) Uani 1 1 d . . . . .
H21 H 1.077154 0.725397 0.187051 0.035 Uiso 1 1 calc R U . . .
C22 C 0.94414(14) 0.71651(12) 0.25199(16) 0.0239(4) Uani 1 1 d . . . . .
H22 H 0.894032 0.735781 0.177409 0.029 Uiso 1 1 calc R U . . .
C23 C 0.70914(13) 0.61282(12) 0.25199(17) 0.0250(4) Uani 1 1 d . . . . .
C24 C 0.68981(16) 0.53489(13) 0.3017(2) 0.0344(4) Uani 1 1 d . . . . .
H24 H 0.705359 0.527637 0.389931 0.041 Uiso 1 1 calc R U . . .
C25 C 0.64730(18) 0.46710(14) 0.2212(3) 0.0457(6) Uani 1 1 d . . . . .
H25 H 0.634178 0.413510 0.254717 0.055 Uiso 1 1 calc R U . . .
C26 C 0.62446(16) 0.47801(15) 0.0935(2) 0.0445(6) Uani 1 1 d . . . . .
H26 H 0.594720 0.431962 0.039200 0.053 Uiso 1 1 calc R U . . .
C27 C 0.64422(15) 0.55477(15) 0.0437(2) 0.0382(5) Uani 1 1 d . . . . .
H27 H 0.628677 0.561332 -0.044630 0.046 Uiso 1 1 calc R U . . .
C28 C 0.68698(14) 0.62310(13) 0.12222(18) 0.0287(4) Uani 1 1 d . . . . .
H28 H 0.700935 0.676142 0.087860 0.034 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 1.4881(13) . ?
P1 C9 1.7981(18) . ?
P1 C17 1.8077(17) . ?
P1 C23 1.8082(19) . ?
F1 C 1.326(2) . ?
F1B O1 1.237(6) . ?
O1 C 1.363(2) . ?
O1 C10 1.372(2) . ?
C C7 1.339(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.401(2) . ?
C1 C7 1.473(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C9 1.453(2) . ?
C9 C10 1.387(2) . ?
C10 C11 1.460(2) . ?
C11 C12 1.392(3) . ?
C11 C16 1.393(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(2) . ?
C17 C22 1.395(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(3) . ?
C23 C28 1.398(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.398(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.376(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.374(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.394(3) . ?
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
O2 P1 C9 114.24(8) . . ?
O2 P1 C17 111.44(8) . . ?
O2 P1 C23 113.22(8) . . ?
C9 P1 C17 109.28(8) . . ?
C9 P1 C23 104.70(8) . . ?
C17 P1 C23 103.20(8) . . ?
F1B O1 C 108.3(3) . . ?
F1B O1 C10 141.1(3) . . ?
C O1 C10 106.18(14) . . ?
F1 C O1 111.18(16) . . ?
F1 C C7 135.28(18) . . ?
C7 C O1 113.22(15) . . ?
C2 C1 C6 118.27(17) . . ?
C2 C1 C7 121.45(16) . . ?
C6 C1 C7 120.28(17) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.80(17) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.33(19) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.45(18) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.45(18) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.65(18) . . ?
C5 C6 H6 119.7 . . ?
C C7 C1 124.26(17) . . ?
C C7 C9 104.69(16) . . ?
C9 C7 C1 131.04(17) . . ?
C7 C9 P1 124.84(13) . . ?
C10 C9 P1 128.35(13) . . ?
C10 C9 C7 106.48(15) . . ?
O1 C10 C9 109.35(15) . . ?
O1 C10 C11 116.38(16) . . ?
C9 C10 C11 134.27(16) . . ?
C12 C11 C10 120.56(16) . . ?
C12 C11 C16 119.46(17) . . ?
C16 C11 C10 119.97(17) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.93(18) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.18(19) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.14(18) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.95(19) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.21(19) . . ?
C15 C16 H16 119.9 . . ?
C18 C17 P1 116.20(13) . . ?
C18 C17 C22 119.96(16) . . ?
C22 C17 P1 123.74(13) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.99(17) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.96(18) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.20(17) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.29(17) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 120.2 . . ?
C21 C22 C17 119.57(17) . . ?
C21 C22 H22 120.2 . . ?
C24 C23 P1 118.24(15) . . ?
C24 C23 C28 120.08(18) . . ?
C28 C23 P1 121.60(15) . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.6(2) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0(2) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.7(2) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.3(2) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 H28 120.3 . . ?
C27 C28 C23 119.4(2) . . ?
C27 C28 H28 120.3 . . ?

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 C9 C10 O1 172.73(12) . . . . ?
P1 C9 C10 C11 -6.8(3) . . . . ?
P1 C17 C18 C19 177.51(15) . . . . ?
P1 C17 C22 C21 -177.86(14) . . . . ?
P1 C23 C24 C25 -177.25(15) . . . . ?
P1 C23 C28 C27 177.40(14) . . . . ?
F1 C C7 C1 3.4(3) . . . . ?
F1 C C7 C9 -175.6(2) . . . . ?
F1B O1 C C7 164.2(3) . . . . ?
F1B O1 C10 C9 -152.6(5) . . . . ?
F1B O1 C10 C11 27.0(6) . . . . ?
O1 C C7 C1 176.03(16) . . . . ?
O1 C C7 C9 -3.0(2) . . . . ?
O1 C10 C11 C12 142.15(17) . . . . ?
O1 C10 C11 C16 -39.1(2) . . . . ?
O2 P1 C9 C7 -83.12(16) . . . . ?
O2 P1 C9 C10 104.42(16) . . . . ?
O2 P1 C17 C18 12.41(16) . . . . ?
O2 P1 C17 C22 -171.10(14) . . . . ?
O2 P1 C23 C24 -19.46(17) . . . . ?
O2 P1 C23 C28 163.85(14) . . . . ?
C O1 C10 C9 -0.91(19) . . . . ?
C O1 C10 C11 178.69(15) . . . . ?
C C7 C9 P1 -171.58(13) . . . . ?
C C7 C9 C10 2.26(19) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C1 C7 C9 P1 9.5(3) . . . . ?
C1 C7 C9 C10 -176.67(18) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C2 C1 C7 C -147.28(19) . . . . ?
C2 C1 C7 C9 31.5(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C6 C1 C2 C3 2.3(3) . . . . ?
C6 C1 C7 C 32.3(3) . . . . ?
C6 C1 C7 C9 -148.96(19) . . . . ?
C7 C1 C2 C3 -178.14(18) . . . . ?
C7 C1 C6 C5 179.50(17) . . . . ?
C7 C9 C10 O1 -0.83(19) . . . . ?
C7 C9 C10 C11 179.67(18) . . . . ?
C9 P1 C17 C18 139.62(14) . . . . ?
C9 P1 C17 C22 -43.90(17) . . . . ?
C9 P1 C23 C24 -144.52(15) . . . . ?
C9 P1 C23 C28 38.79(16) . . . . ?
C9 C10 C11 C12 -38.4(3) . . . . ?
C9 C10 C11 C16 140.3(2) . . . . ?
C10 O1 C F1 176.99(15) . . . . ?
C10 O1 C C7 2.5(2) . . . . ?
C10 C11 C12 C13 175.01(17) . . . . ?
C10 C11 C16 C15 -175.89(18) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C11 C16 C15 2.8(3) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
C13 C14 C15 C16 -2.6(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C16 C11 C12 C13 -3.7(3) . . . . ?
C17 P1 C9 C7 151.28(14) . . . . ?
C17 P1 C9 C10 -21.18(18) . . . . ?
C17 P1 C23 C24 101.14(15) . . . . ?
C17 P1 C23 C28 -75.55(16) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C17 C22 C21 -1.5(3) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 0.1(3) . . . . ?
C20 C21 C22 C17 1.0(3) . . . . ?
C22 C17 C18 C19 0.9(3) . . . . ?
C23 P1 C9 C7 41.30(16) . . . . ?
C23 P1 C9 C10 -131.17(16) . . . . ?
C23 P1 C17 C18 -109.40(14) . . . . ?
C23 P1 C17 C22 67.09(16) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C24 C23 C28 C27 0.8(3) . . . . ?
C24 C25 C26 C27 0.8(3) . . . . ?
C25 C26 C27 C28 -0.5(3) . . . . ?
C26 C27 C28 C23 -0.2(3) . . . . ?
C28 C23 C24 C25 -0.5(3) . . . . ?

_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 2.185
_oxdiff_exptl_absorpt_empirical_full_min 0.558
####################################################################### 
# 
# 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_1726
_database_code_depnum_ccdc_archive 'CCDC 2284384'
loop_
_audit_author_name
_audit_author_address
cxq
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;
_audit_creation_date             2023-07-25
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 F4 O2 P'
_chemical_formula_sum            'C23 H15 F4 O2 P'
_chemical_formula_weight         430.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   16.8764(3)
_cell_length_b                   20.6631(4)
_cell_length_c                   11.3864(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.772(2)
_cell_angle_gamma                90
_cell_volume                     3966.00(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6717
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.3000
_cell_measurement_theta_min      3.3560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16062
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.562
_diffrn_reflns_theta_min         2.621
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  29.00   1.00    1.00    --  -40.73  38.00 -90.00   47
  2  ω     25.00  65.00   1.00    1.00    --   40.73 -38.00-120.00   40
  3  ω     62.00  96.00   1.00    1.00    --   40.73-125.00-120.00   34
  4  ω     53.00  93.00   1.00    1.00    --  106.95 -94.00-180.00   40
  5  ω     56.00 107.00   1.00    1.00    --  106.95 -94.00-120.00   51
  6  ω     36.00 122.00   1.00    1.00    --  106.95 -30.00-180.00   86
  7  ω    114.00 170.00   1.00    1.00    --  106.95  45.00-180.00   56
  8  ω    128.00 174.00   1.00    1.00    --  106.95 125.00-120.00   46
  9  ω    149.00 176.00   1.00    1.00    --  106.95  15.00  30.00   27
 10  ω     57.00 113.00   1.00    1.00    --  106.95  15.00  30.00   56
 11  ω     37.00 121.00   1.00    1.00    --  106.95-125.00 120.00   84
 12  ω    -63.00 -25.00   1.00    1.00    --  -40.73  38.00 -90.00   38
 13  ω    -62.00  32.00   1.00    1.00    --  -40.73  57.00 120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0500825000
_diffrn_orient_matrix_UB_12      0.0617555000
_diffrn_orient_matrix_UB_13      0.0122935000
_diffrn_orient_matrix_UB_21      -0.0764172000
_diffrn_orient_matrix_UB_22      -0.0407818000
_diffrn_orient_matrix_UB_23      -0.0108964000
_diffrn_orient_matrix_UB_31      0.0027797000
_diffrn_orient_matrix_UB_32      -0.0088638000
_diffrn_orient_matrix_UB_33      0.1344680000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6251
_reflns_number_total             7786
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         7786
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.078
_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)+(0.0661P)²+0.4095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1415
_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), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38),
 C39(H39), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45)
;
_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 0.34573(3) 0.75553(3) 0.73221(4) 0.02351(14) Uani 1 1 d . . . . .
F1 F 0.36142(11) 0.60259(8) 0.76118(13) 0.0551(4) Uani 1 1 d . . . . .
F2 F 0.32689(11) 0.57293(8) 0.58717(15) 0.0613(5) Uani 1 1 d . . . . .
F3 F 0.43974(12) 0.54507(8) 0.66190(19) 0.0739(6) Uani 1 1 d . . . . .
F7 F 0.51568(9) 0.60431(7) 0.47430(13) 0.0466(4) Uani 1 1 d . . . . .
O1 O 0.36255(9) 0.74877(8) 0.86005(13) 0.0313(4) Uani 1 1 d . . . . .
O2 O 0.51477(9) 0.70978(8) 0.51109(13) 0.0303(3) Uani 1 1 d . . . . .
C1 C 0.25486(12) 0.71654(10) 0.68061(18) 0.0258(4) Uani 1 1 d . . . . .
C2 C 0.19763(13) 0.70335(11) 0.76117(19) 0.0311(5) Uani 1 1 d . . . . .
H2 H 0.207828 0.712793 0.842145 0.037 Uiso 1 1 calc R U . . .
C3 C 0.12581(14) 0.67644(12) 0.7232(2) 0.0349(5) Uani 1 1 d . . . . .
H3 H 0.086337 0.668434 0.778122 0.042 Uiso 1 1 calc R U . . .
C4 C 0.11101(14) 0.66110(12) 0.6060(2) 0.0372(5) Uani 1 1 d . . . . .
H4 H 0.062051 0.641816 0.580477 0.045 Uiso 1 1 calc R U . . .
C5 C 0.16831(15) 0.67415(13) 0.5260(2) 0.0380(6) Uani 1 1 d . . . . .
H5 H 0.158381 0.663823 0.445307 0.046 Uiso 1 1 calc R U . . .
C6 C 0.23991(13) 0.70210(12) 0.56263(19) 0.0314(5) Uani 1 1 d . . . . .
H6 H 0.278633 0.711344 0.507161 0.038 Uiso 1 1 calc R U . . .
C7 C 0.33066(12) 0.83895(11) 0.68939(18) 0.0260(4) Uani 1 1 d . . . . .
C8 C 0.32456(15) 0.88373(12) 0.7801(2) 0.0356(5) Uani 1 1 d . . . . .
H8 H 0.332608 0.870467 0.859688 0.043 Uiso 1 1 calc R U . . .
C9 C 0.30668(17) 0.94775(13) 0.7536(2) 0.0451(6) Uani 1 1 d . . . . .
H9 H 0.301990 0.978314 0.815163 0.054 Uiso 1 1 calc R U . . .
C10 C 0.29571(17) 0.96714(12) 0.6385(2) 0.0450(6) Uani 1 1 d . . . . .
H10 H 0.283953 1.011137 0.620835 0.054 Uiso 1 1 calc R U . . .
C11 C 0.30175(15) 0.92282(12) 0.5484(2) 0.0373(5) Uani 1 1 d . . . . .
H11 H 0.293979 0.936577 0.469113 0.045 Uiso 1 1 calc R U . . .
C12 C 0.31897(13) 0.85873(11) 0.57277(19) 0.0294(5) Uani 1 1 d . . . . .
H12 H 0.322817 0.828395 0.510611 0.035 Uiso 1 1 calc R U . . .
C13 C 0.47500(12) 0.75284(10) 0.58150(18) 0.0251(4) Uani 1 1 d . . . . .
C14 C 0.50416(12) 0.81924(11) 0.57678(19) 0.0291(5) Uani 1 1 d . . . . .
C15 C 0.51697(14) 0.85343(12) 0.6812(2) 0.0375(5) Uani 1 1 d . . . . .
H15 H 0.505273 0.834067 0.754032 0.045 Uiso 1 1 calc R U . . .
C16 C 0.54679(17) 0.91572(13) 0.6786(3) 0.0484(7) Uani 1 1 d . . . . .
H16 H 0.555187 0.939360 0.749674 0.058 Uiso 1 1 calc R U . . .
C17 C 0.56441(18) 0.94362(14) 0.5726(3) 0.0553(8) Uani 1 1 d . . . . .
H17 H 0.585341 0.986278 0.571161 0.066 Uiso 1 1 calc R U . . .
C18 C 0.55177(18) 0.90988(14) 0.4689(3) 0.0518(7) Uani 1 1 d . . . . .
H18 H 0.563716 0.929436 0.396373 0.062 Uiso 1 1 calc R U . . .
C19 C 0.52163(15) 0.84743(12) 0.4703(2) 0.0373(5) Uani 1 1 d . . . . .
H19 H 0.512994 0.824100 0.398939 0.045 Uiso 1 1 calc R U . . .
C20 C 0.48365(14) 0.65191(11) 0.5319(2) 0.0329(5) Uani 1 1 d . . . . .
C21 C 0.42704(13) 0.65285(11) 0.60991(18) 0.0284(5) Uani 1 1 d . . . . .
C22 C 0.38856(16) 0.59383(12) 0.6551(2) 0.0379(5) Uani 1 1 d . . . . .
C23 C 0.41968(12) 0.72101(10) 0.64206(17) 0.0245(4) Uani 1 1 d . . . . .
P2 P 0.86441(3) 0.75769(3) 0.05741(4) 0.02484(14) Uani 1 1 d . . . . .
F4 F 0.74579(9) 0.88677(8) 0.23977(17) 0.0593(5) Uani 1 1 d . . . . .
F5 F 0.71242(10) 0.86161(9) 0.06137(15) 0.0574(4) Uani 1 1 d . . . . .
F6 F 0.62732(9) 0.85645(9) 0.19579(15) 0.0557(4) Uani 1 1 d . . . . .
F8 F 0.62530(11) 0.74810(9) 0.33351(18) 0.0703(6) Uani 1 1 d . . . . .
O5 O 0.70634(10) 0.67557(9) 0.26143(16) 0.0427(4) Uani 1 1 d . . . . .
O6 O 0.84855(9) 0.75353(8) -0.07115(13) 0.0339(4) Uani 1 1 d . . . . .
C24 C 0.72379(13) 0.77601(12) 0.1950(2) 0.0342(5) Uani 1 1 d . . . . .
C25 C 0.68344(15) 0.73690(14) 0.2635(2) 0.0445(6) Uani 1 1 d . . . . .
C26 C 0.78267(12) 0.73399(11) 0.14479(18) 0.0271(4) Uani 1 1 d . . . . .
C27 C 0.76733(13) 0.67290(12) 0.18453(19) 0.0311(5) Uani 1 1 d . . . . .
C28 C 0.79795(13) 0.60832(11) 0.1663(2) 0.0328(5) Uani 1 1 d . . . . .
C29 C 0.79215(15) 0.56159(13) 0.2545(2) 0.0410(6) Uani 1 1 d . . . . .
H29 H 0.766766 0.571959 0.324752 0.049 Uiso 1 1 calc R U . . .
C30 C 0.82327(17) 0.50039(13) 0.2397(2) 0.0477(7) Uani 1 1 d . . . . .
H30 H 0.819139 0.468828 0.299726 0.057 Uiso 1 1 calc R U . . .
C31 C 0.86008(18) 0.48511(14) 0.1385(3) 0.0520(7) Uani 1 1 d . . . . .
H31 H 0.882816 0.443429 0.129727 0.062 Uiso 1 1 calc R U . . .
C32 C 0.86422(17) 0.53030(13) 0.0489(2) 0.0471(6) Uani 1 1 d . . . . .
H32 H 0.888623 0.519119 -0.021774 0.057 Uiso 1 1 calc R U . . .
C33 C 0.83302(15) 0.59145(12) 0.0621(2) 0.0373(5) Uani 1 1 d . . . . .
H33 H 0.835402 0.622095 0.000154 0.045 Uiso 1 1 calc R U . . .
C34 C 0.94944(12) 0.70969(10) 0.10836(18) 0.0251(4) Uani 1 1 d . . . . .
C35 C 1.00703(13) 0.69789(11) 0.02761(19) 0.0307(5) Uani 1 1 d . . . . .
H35 H 0.999450 0.712834 -0.051033 0.037 Uiso 1 1 calc R U . . .
C36 C 1.07575(14) 0.66421(12) 0.0619(2) 0.0370(5) Uani 1 1 d . . . . .
H36 H 1.115234 0.656706 0.006801 0.044 Uiso 1 1 calc R U . . .
C37 C 1.08682(14) 0.64165(12) 0.1758(2) 0.0383(6) Uani 1 1 d . . . . .
H37 H 1.133353 0.618145 0.199048 0.046 Uiso 1 1 calc R U . . .
C38 C 1.02915(14) 0.65375(12) 0.2558(2) 0.0350(5) Uani 1 1 d . . . . .
H38 H 1.036486 0.638259 0.334101 0.042 Uiso 1 1 calc R U . . .
C39 C 0.96103(13) 0.68804(11) 0.22331(18) 0.0279(4) Uani 1 1 d . . . . .
H39 H 0.922498 0.696688 0.279365 0.033 Uiso 1 1 calc R U . . .
C40 C 0.89116(12) 0.83851(11) 0.10542(18) 0.0274(5) Uani 1 1 d . . . . .
C41 C 0.91269(13) 0.85194(11) 0.2222(2) 0.0319(5) Uani 1 1 d . . . . .
H41 H 0.909634 0.819122 0.280253 0.038 Uiso 1 1 calc R U . . .
C42 C 0.93854(15) 0.91323(13) 0.2535(2) 0.0413(6) Uani 1 1 d . . . . .
H42 H 0.954351 0.922241 0.333025 0.050 Uiso 1 1 calc R U . . .
C43 C 0.94161(17) 0.96169(14) 0.1698(3) 0.0503(7) Uani 1 1 d . . . . .
H43 H 0.959274 1.003806 0.191943 0.060 Uiso 1 1 calc R U . . .
C44 C 0.91896(16) 0.94869(13) 0.0541(3) 0.0468(6) Uani 1 1 d . . . . .
H44 H 0.920264 0.982058 -0.003130 0.056 Uiso 1 1 calc R U . . .
C45 C 0.89438(14) 0.88716(12) 0.0214(2) 0.0363(5) Uani 1 1 d . . . . .
H45 H 0.879683 0.878130 -0.058492 0.044 Uiso 1 1 calc R U . . .
C46 C 0.70321(15) 0.84478(14) 0.1733(2) 0.0428(6) Uani 1 1 d . . . . .


_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 1.4761(15) . ?
P1 C1 1.805(2) . ?
P1 C7 1.806(2) . ?
P1 C23 1.801(2) . ?
F1 C22 1.324(3) . ?
F2 C22 1.338(3) . ?
F3 C22 1.327(3) . ?
F7 C20 1.313(3) . ?
O2 C13 1.392(2) . ?
O2 C20 1.332(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.387(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(3) . ?
C7 C12 1.394(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.459(3) . ?
C13 C23 1.357(3) . ?
C14 C15 1.391(3) . ?
C14 C19 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.336(3) . ?
C21 C22 1.485(3) . ?
C21 C23 1.462(3) . ?
P2 O6 1.4778(16) . ?
P2 C26 1.807(2) . ?
P2 C34 1.816(2) . ?
P2 C40 1.808(2) . ?
F4 C46 1.338(3) . ?
F5 C46 1.338(3) . ?
F6 C46 1.340(3) . ?
F8 C25 1.315(3) . ?
O5 C25 1.325(3) . ?
O5 C27 1.384(3) . ?
C24 C25 1.333(4) . ?
C24 C26 1.457(3) . ?
C24 C46 1.481(4) . ?
C26 C27 1.370(3) . ?
C27 C28 1.449(3) . ?
C28 C29 1.400(3) . ?
C28 C33 1.396(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.383(4) . ?
C30 H30 0.9500 . ?
C30 C31 1.372(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.387(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.380(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.391(3) . ?
C34 C39 1.388(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.392(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.382(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.387(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.385(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.390(3) . ?
C40 C45 1.390(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.381(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.385(4) . ?
C43 H43 0.9500 . ?
C43 C44 1.380(4) . ?
C44 H44 0.9500 . ?
C44 C45 1.383(4) . ?
C45 H45 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 C1 113.49(10) . . ?
O1 P1 C7 111.99(10) . . ?
O1 P1 C23 114.77(9) . . ?
C1 P1 C7 103.40(10) . . ?
C23 P1 C1 103.82(10) . . ?
C23 P1 C7 108.46(10) . . ?
C20 O2 C13 105.45(17) . . ?
C2 C1 P1 118.62(16) . . ?
C6 C1 P1 121.54(16) . . ?
C6 C1 C2 119.8(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C8 C7 P1 116.60(17) . . ?
C12 C7 P1 123.26(17) . . ?
C12 C7 C8 119.9(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 120.3 . . ?
C11 C12 C7 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
O2 C13 C14 114.02(18) . . ?
C23 C13 O2 110.21(18) . . ?
C23 C13 C14 135.7(2) . . ?
C15 C14 C13 119.0(2) . . ?
C19 C14 C13 120.8(2) . . ?
C19 C14 C15 120.1(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 120.2 . . ?
C18 C19 C14 119.5(2) . . ?
C18 C19 H19 120.2 . . ?
F7 C20 O2 114.1(2) . . ?
F7 C20 C21 131.9(2) . . ?
O2 C20 C21 114.0(2) . . ?
C20 C21 C22 123.9(2) . . ?
C20 C21 C23 104.6(2) . . ?
C23 C21 C22 131.3(2) . . ?
F1 C22 F2 106.1(2) . . ?
F1 C22 F3 107.7(2) . . ?
F1 C22 C21 112.3(2) . . ?
F2 C22 C21 113.92(19) . . ?
F3 C22 F2 105.9(2) . . ?
F3 C22 C21 110.4(2) . . ?
C13 C23 P1 127.61(17) . . ?
C13 C23 C21 105.71(19) . . ?
C21 C23 P1 126.43(16) . . ?
O6 P2 C26 115.03(9) . . ?
O6 P2 C34 112.77(10) . . ?
O6 P2 C40 112.58(10) . . ?
C26 P2 C34 106.77(10) . . ?
C26 P2 C40 105.66(10) . . ?
C40 P2 C34 103.06(10) . . ?
C25 O5 C27 105.99(19) . . ?
C25 C24 C26 104.2(2) . . ?
C25 C24 C46 123.9(2) . . ?
C26 C24 C46 131.7(2) . . ?
F8 C25 O5 113.9(2) . . ?
F8 C25 C24 131.7(3) . . ?
O5 C25 C24 114.3(2) . . ?
C24 C26 P2 127.43(18) . . ?
C27 C26 P2 126.37(18) . . ?
C27 C26 C24 106.0(2) . . ?
O5 C27 C28 114.1(2) . . ?
C26 C27 O5 109.3(2) . . ?
C26 C27 C28 136.6(2) . . ?
C29 C28 C27 119.7(2) . . ?
C33 C28 C27 121.3(2) . . ?
C33 C28 C29 119.0(2) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.2(2) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.2(3) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.2(3) . . ?
C32 C31 H31 119.9 . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.2(3) . . ?
C33 C32 H32 119.9 . . ?
C28 C33 H33 120.0 . . ?
C32 C33 C28 120.1(2) . . ?
C32 C33 H33 120.0 . . ?
C35 C34 P2 116.81(16) . . ?
C39 C34 P2 123.39(16) . . ?
C39 C34 C35 119.7(2) . . ?
C34 C35 H35 120.0 . . ?
C34 C35 C36 120.1(2) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.3(2) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 120.4 . . ?
C36 C37 C38 119.2(2) . . ?
C38 C37 H37 120.4 . . ?
C37 C38 H38 119.5 . . ?
C39 C38 C37 121.1(2) . . ?
C39 C38 H38 119.5 . . ?
C34 C39 H39 120.2 . . ?
C38 C39 C34 119.6(2) . . ?
C38 C39 H39 120.2 . . ?
C41 C40 P2 121.59(17) . . ?
C41 C40 C45 119.8(2) . . ?
C45 C40 P2 118.52(17) . . ?
C40 C41 H41 120.2 . . ?
C42 C41 C40 119.7(2) . . ?
C42 C41 H41 120.2 . . ?
C41 C42 H42 119.8 . . ?
C41 C42 C43 120.5(2) . . ?
C43 C42 H42 119.8 . . ?
C42 C43 H43 120.1 . . ?
C44 C43 C42 119.9(3) . . ?
C44 C43 H43 120.1 . . ?
C43 C44 H44 119.9 . . ?
C43 C44 C45 120.1(2) . . ?
C45 C44 H44 119.9 . . ?
C40 C45 H45 120.0 . . ?
C44 C45 C40 120.0(2) . . ?
C44 C45 H45 120.0 . . ?
F4 C46 F5 106.6(2) . . ?
F4 C46 F6 105.5(2) . . ?
F4 C46 C24 114.4(2) . . ?
F5 C46 F6 106.9(2) . . ?
F5 C46 C24 111.8(2) . . ?
F6 C46 C24 111.1(2) . . ?

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 C1 C2 C3 176.79(18) . . . . ?
P1 C1 C6 C5 -177.81(19) . . . . ?
P1 C7 C8 C9 -174.9(2) . . . . ?
P1 C7 C12 C11 174.98(18) . . . . ?
F7 C20 C21 C22 3.5(4) . . . . ?
F7 C20 C21 C23 179.1(2) . . . . ?
O1 P1 C1 C2 20.7(2) . . . . ?
O1 P1 C1 C6 -161.99(18) . . . . ?
O1 P1 C7 C8 -9.4(2) . . . . ?
O1 P1 C7 C12 175.71(17) . . . . ?
O1 P1 C23 C13 -105.1(2) . . . . ?
O1 P1 C23 C21 81.5(2) . . . . ?
O2 C13 C14 C15 -134.6(2) . . . . ?
O2 C13 C14 C19 43.2(3) . . . . ?
O2 C13 C23 P1 -172.70(14) . . . . ?
O2 C13 C23 C21 1.8(2) . . . . ?
O2 C20 C21 C22 -174.5(2) . . . . ?
O2 C20 C21 C23 1.2(3) . . . . ?
C1 P1 C7 C8 113.12(18) . . . . ?
C1 P1 C7 C12 -61.7(2) . . . . ?
C1 P1 C23 C13 130.50(19) . . . . ?
C1 P1 C23 C21 -42.9(2) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C7 P1 C1 C2 -100.86(19) . . . . ?
C7 P1 C1 C6 76.5(2) . . . . ?
C7 P1 C23 C13 21.0(2) . . . . ?
C7 P1 C23 C21 -152.41(18) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C7 -0.3(4) . . . . ?
C12 C7 C8 C9 0.2(4) . . . . ?
C13 O2 C20 F7 -178.46(18) . . . . ?
C13 O2 C20 C21 -0.2(2) . . . . ?
C13 C14 C15 C16 178.1(2) . . . . ?
C13 C14 C19 C18 -177.9(2) . . . . ?
C14 C13 C23 P1 10.5(4) . . . . ?
C14 C13 C23 C21 -175.0(2) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C15 C14 C19 C18 -0.1(4) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C17 C18 C19 C14 0.1(4) . . . . ?
C19 C14 C15 C16 0.3(4) . . . . ?
C20 O2 C13 C14 176.45(18) . . . . ?
C20 O2 C13 C23 -1.1(2) . . . . ?
C20 C21 C22 F1 153.4(2) . . . . ?
C20 C21 C22 F2 -85.9(3) . . . . ?
C20 C21 C22 F3 33.1(3) . . . . ?
C20 C21 C23 P1 172.77(16) . . . . ?
C20 C21 C23 C13 -1.8(2) . . . . ?
C22 C21 C23 P1 -12.0(3) . . . . ?
C22 C21 C23 C13 173.4(2) . . . . ?
C23 P1 C1 C2 145.95(18) . . . . ?
C23 P1 C1 C6 -36.7(2) . . . . ?
C23 P1 C7 C8 -137.10(17) . . . . ?
C23 P1 C7 C12 48.0(2) . . . . ?
C23 C13 C14 C15 42.1(4) . . . . ?
C23 C13 C14 C19 -140.1(3) . . . . ?
C23 C21 C22 F1 -21.1(4) . . . . ?
C23 C21 C22 F2 99.6(3) . . . . ?
C23 C21 C22 F3 -141.3(2) . . . . ?
P2 C26 C27 O5 171.86(15) . . . . ?
P2 C26 C27 C28 -8.4(4) . . . . ?
P2 C34 C35 C36 176.82(18) . . . . ?
P2 C34 C39 C38 -177.54(17) . . . . ?
P2 C40 C41 C42 175.03(18) . . . . ?
P2 C40 C45 C44 -176.34(19) . . . . ?
O5 C27 C28 C29 -26.8(3) . . . . ?
O5 C27 C28 C33 152.9(2) . . . . ?
O6 P2 C26 C24 -95.7(2) . . . . ?
O6 P2 C26 C27 89.6(2) . . . . ?
O6 P2 C34 C35 25.9(2) . . . . ?
O6 P2 C34 C39 -157.80(18) . . . . ?
O6 P2 C40 C41 -176.36(17) . . . . ?
O6 P2 C40 C45 -0.1(2) . . . . ?
C24 C26 C27 O5 -3.8(2) . . . . ?
C24 C26 C27 C28 176.0(2) . . . . ?
C25 O5 C27 C26 2.6(3) . . . . ?
C25 O5 C27 C28 -177.2(2) . . . . ?
C25 C24 C26 P2 -172.09(18) . . . . ?
C25 C24 C26 C27 3.5(3) . . . . ?
C25 C24 C46 F4 98.2(3) . . . . ?
C25 C24 C46 F5 -140.4(3) . . . . ?
C25 C24 C46 F6 -21.1(4) . . . . ?
C26 P2 C34 C35 153.16(17) . . . . ?
C26 P2 C34 C39 -30.5(2) . . . . ?
C26 P2 C40 C41 57.3(2) . . . . ?
C26 P2 C40 C45 -126.40(18) . . . . ?
C26 C24 C25 F8 177.4(3) . . . . ?
C26 C24 C25 O5 -2.0(3) . . . . ?
C26 C24 C46 F4 -87.9(3) . . . . ?
C26 C24 C46 F5 33.4(4) . . . . ?
C26 C24 C46 F6 152.7(2) . . . . ?
C26 C27 C28 C29 153.4(3) . . . . ?
C26 C27 C28 C33 -26.8(4) . . . . ?
C27 O5 C25 F8 -179.8(2) . . . . ?
C27 O5 C25 C24 -0.2(3) . . . . ?
C27 C28 C29 C30 -178.1(2) . . . . ?
C27 C28 C33 C32 177.7(2) . . . . ?
C28 C29 C30 C31 0.1(4) . . . . ?
C29 C28 C33 C32 -2.6(4) . . . . ?
C29 C30 C31 C32 -2.0(4) . . . . ?
C30 C31 C32 C33 1.6(4) . . . . ?
C31 C32 C33 C28 0.8(4) . . . . ?
C33 C28 C29 C30 2.2(4) . . . . ?
C34 P2 C26 C24 138.34(19) . . . . ?
C34 P2 C26 C27 -36.4(2) . . . . ?
C34 P2 C40 C41 -54.6(2) . . . . ?
C34 P2 C40 C45 121.72(18) . . . . ?
C34 C35 C36 C37 0.8(4) . . . . ?
C35 C34 C39 C38 -1.3(3) . . . . ?
C35 C36 C37 C38 -0.9(4) . . . . ?
C36 C37 C38 C39 -0.1(4) . . . . ?
C37 C38 C39 C34 1.2(4) . . . . ?
C39 C34 C35 C36 0.3(3) . . . . ?
C40 P2 C26 C24 29.1(2) . . . . ?
C40 P2 C26 C27 -145.61(19) . . . . ?
C40 P2 C34 C35 -95.78(18) . . . . ?
C40 P2 C34 C39 80.5(2) . . . . ?
C40 C41 C42 C43 1.3(4) . . . . ?
C41 C40 C45 C44 0.0(3) . . . . ?
C41 C42 C43 C44 -0.2(4) . . . . ?
C42 C43 C44 C45 -1.0(4) . . . . ?
C43 C44 C45 C40 1.1(4) . . . . ?
C45 C40 C41 C42 -1.2(3) . . . . ?
C46 C24 C25 F8 -7.3(5) . . . . ?
C46 C24 C25 O5 173.2(2) . . . . ?
C46 C24 C26 P2 13.2(4) . . . . ?
C46 C24 C26 C27 -171.2(2) . . . . ?

_olex2_date_sample_data_collection 2023-07-24
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.610
