# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_dan
_database_code_depnum_ccdc_archive 'CCDC 2024116'
loop_
_audit_author_name
_audit_author_address
Xue-Qiang
;Nanjing Tech
China
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2023-02-04 downloaded from the CCDC.
;
_audit_creation_date             2020-08-19
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 F5 O2 P'
_chemical_formula_sum            'C24 H16 F5 O2 P'
_chemical_formula_weight         462.34
_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 0.0033 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'
F F 0.0171 0.0103 '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      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                   18.8874(14)
_cell_length_b                   6.1813(5)
_cell_length_c                   17.2323(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.402(6)
_cell_angle_gamma                90
_cell_volume                     2011.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3255
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.8580
_cell_measurement_theta_min      2.5670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69081
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8029
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.157
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00  21.00   1.00    1.20    --  -11.43 -77.00  90.00  109
  2  ω    -51.00 -24.00   1.00    1.20    --  -11.43 104.00 -44.00   27
  3  ω     38.00  99.00   1.00    1.20    --   12.05-178.00 -30.00   61
;
_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      0.0032267000
_diffrn_orient_matrix_UB_12      -0.1060596000
_diffrn_orient_matrix_UB_13      0.0153990000
_diffrn_orient_matrix_UB_21      0.0360794000
_diffrn_orient_matrix_UB_22      -0.0026528000
_diffrn_orient_matrix_UB_23      -0.0104928000
_diffrn_orient_matrix_UB_31      0.0099548000
_diffrn_orient_matrix_UB_32      0.0436317000
_diffrn_orient_matrix_UB_33      0.0367223000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2956
_reflns_number_total             3550
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.053
_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)+(0.0444P)²+0.8541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1029
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_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 0.77360(3) 0.27653(9) 0.76762(3) 0.01742(16) Uani 1 1 d . . . . .
F1 F 0.53681(7) 0.8407(2) 0.74820(7) 0.0363(4) Uani 1 1 d . . . . .
F2 F 0.59405(7) 1.0704(2) 0.67565(8) 0.0367(4) Uani 1 1 d . . . . .
F3 F 0.55483(7) 0.8407(3) 0.54783(7) 0.0389(4) Uani 1 1 d . . . . .
F4 F 0.46765(7) 0.9428(3) 0.61622(7) 0.0435(4) Uani 1 1 d . . . . .
F5 F 0.50117(8) 0.6105(3) 0.61801(8) 0.0474(4) Uani 1 1 d . . . . .
O1 O 0.78259(8) 0.0737(2) 0.72288(8) 0.0224(3) Uani 1 1 d . . . . .
O2 O 0.68780(7) 0.7424(2) 0.63484(7) 0.0182(3) Uani 1 1 d . . . . .
C1 C 0.87805(11) 0.6078(4) 0.78521(11) 0.0199(5) Uani 1 1 d . . . . .
H1 H 0.846733 0.706442 0.762362 0.024 Uiso 1 1 calc R U . . .
C2 C 0.94612(11) 0.6721(4) 0.80750(11) 0.0231(5) Uani 1 1 d . . . . .
H2 H 0.960355 0.813968 0.798915 0.028 Uiso 1 1 calc R U . . .
C3 C 0.99278(12) 0.5277(4) 0.84221(12) 0.0252(5) Uani 1 1 d . . . . .
H3 H 1.038348 0.571895 0.856427 0.030 Uiso 1 1 calc R U . . .
C4 C 0.97166(11) 0.3178(4) 0.85577(12) 0.0259(5) Uani 1 1 d . . . . .
H4 H 1.002765 0.220923 0.879949 0.031 Uiso 1 1 calc R U . . .
C5 C 0.90449(11) 0.2512(4) 0.83353(11) 0.0223(5) Uani 1 1 d . . . . .
H5 H 0.890603 0.109358 0.842721 0.027 Uiso 1 1 calc R U . . .
C6 C 0.85715(11) 0.3948(3) 0.79736(11) 0.0182(5) Uani 1 1 d . . . . .
C7 C 0.72711(11) 0.2309(3) 0.85671(11) 0.0181(5) Uani 1 1 d . . . . .
C8 C 0.69831(12) 0.0280(4) 0.86906(12) 0.0247(5) Uani 1 1 d . . . . .
H8 H 0.703253 -0.080072 0.832026 0.030 Uiso 1 1 calc R U . . .
C9 C 0.66220(12) -0.0146(4) 0.93640(13) 0.0289(5) Uani 1 1 d . . . . .
H9 H 0.642772 -0.150785 0.944350 0.035 Uiso 1 1 calc R U . . .
C10 C 0.65500(11) 0.1447(4) 0.99164(12) 0.0255(5) Uani 1 1 d . . . . .
H10 H 0.630395 0.116170 1.036595 0.031 Uiso 1 1 calc R U . . .
C11 C 0.68425(11) 0.3463(4) 0.98033(12) 0.0252(5) Uani 1 1 d . . . . .
H11 H 0.679455 0.453264 1.017800 0.030 Uiso 1 1 calc R U . . .
C12 C 0.72076(11) 0.3902(4) 0.91334(11) 0.0216(5) Uani 1 1 d . . . . .
H12 H 0.740997 0.525663 0.906197 0.026 Uiso 1 1 calc R U . . .
C13 C 0.72346(10) 0.4836(3) 0.71815(11) 0.0170(4) Uani 1 1 d . . . . .
C14 C 0.65560(11) 0.5618(3) 0.74011(11) 0.0200(5) Uani 1 1 d . . . . .
H14 H 0.629380 0.514253 0.781787 0.024 Uiso 1 1 calc R U . . .
C15 C 0.63706(11) 0.7161(3) 0.68934(11) 0.0185(5) Uani 1 1 d . . . . .
C16 C 0.74063(10) 0.5990(3) 0.65288(11) 0.0174(4) Uani 1 1 d . . . . .
C17 C 0.80010(10) 0.5995(3) 0.59994(11) 0.0179(5) Uani 1 1 d . . . . .
C18 C 0.81671(11) 0.7887(4) 0.55999(11) 0.0201(5) Uani 1 1 d . . . . .
H18 H 0.791836 0.915450 0.569503 0.024 Uiso 1 1 calc R U . . .
C19 C 0.86998(11) 0.7886(4) 0.50635(11) 0.0214(5) Uani 1 1 d . . . . .
H19 H 0.880089 0.914062 0.478997 0.026 Uiso 1 1 calc R U . . .
C20 C 0.90807(11) 0.6026(4) 0.49341(11) 0.0221(5) Uani 1 1 d . . . . .
H20 H 0.943999 0.602780 0.457465 0.026 Uiso 1 1 calc R U . . .
C21 C 0.89295(11) 0.4154(4) 0.53383(11) 0.0220(5) Uani 1 1 d . . . . .
H21 H 0.919173 0.290589 0.525365 0.026 Uiso 1 1 calc R U . . .
C22 C 0.83890(11) 0.4128(4) 0.58689(11) 0.0207(5) Uani 1 1 d . . . . .
H22 H 0.828676 0.286389 0.613646 0.025 Uiso 1 1 calc R U . . .
C23 C 0.57491(11) 0.8600(4) 0.68287(12) 0.0236(5) Uani 1 1 d . . . . .
C24 C 0.52329(12) 0.8133(4) 0.61498(12) 0.0284(5) 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 1.4835(15) . ?
P1 C6 1.802(2) . ?
P1 C7 1.809(2) . ?
P1 C13 1.795(2) . ?
F1 C23 1.356(2) . ?
F2 C23 1.356(3) . ?
F3 C24 1.325(2) . ?
F4 C24 1.322(3) . ?
F5 C24 1.323(3) . ?
O2 C15 1.368(2) . ?
O2 C16 1.365(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.391(3) . ?
C1 C6 1.392(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(3) . ?
C7 C8 1.386(3) . ?
C7 C12 1.393(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.429(3) . ?
C13 C16 1.377(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.335(3) . ?
C15 C23 1.475(3) . ?
C16 C17 1.464(3) . ?
C17 C18 1.397(3) . ?
C17 C22 1.389(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.387(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.532(3) . ?

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 C6 112.34(9) . . ?
O1 P1 C7 111.93(9) . . ?
O1 P1 C13 114.92(9) . . ?
C6 P1 C7 105.17(9) . . ?
C13 P1 C6 107.08(10) . . ?
C13 P1 C7 104.63(9) . . ?
C16 O2 C15 106.69(15) . . ?
C2 C1 H1 120.3 . . ?
C2 C1 C6 119.5(2) . . ?
C6 C1 H1 120.3 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 P1 126.20(16) . . ?
C1 C6 C5 119.2(2) . . ?
C5 C6 P1 114.57(16) . . ?
C8 C7 P1 118.15(16) . . ?
C8 C7 C12 119.41(19) . . ?
C12 C7 P1 122.42(16) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.1(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 120.1 . . ?
C11 C12 C7 119.9(2) . . ?
C11 C12 H12 120.1 . . ?
C14 C13 P1 125.55(15) . . ?
C16 C13 P1 128.68(16) . . ?
C16 C13 C14 105.77(18) . . ?
C13 C14 H14 126.6 . . ?
C15 C14 C13 106.89(18) . . ?
C15 C14 H14 126.6 . . ?
O2 C15 C23 116.52(17) . . ?
C14 C15 O2 110.95(18) . . ?
C14 C15 C23 132.52(19) . . ?
O2 C16 C13 109.68(17) . . ?
O2 C16 C17 115.09(17) . . ?
C13 C16 C17 135.22(19) . . ?
C18 C17 C16 119.62(19) . . ?
C22 C17 C16 120.98(19) . . ?
C22 C17 C18 119.36(18) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.10(19) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 120.1 . . ?
C21 C22 C17 119.8(2) . . ?
C21 C22 H22 120.1 . . ?
F1 C23 C15 108.77(17) . . ?
F1 C23 C24 106.06(17) . . ?
F2 C23 F1 107.97(18) . . ?
F2 C23 C15 111.82(18) . . ?
F2 C23 C24 106.07(18) . . ?
C15 C23 C24 115.75(18) . . ?
F3 C24 C23 110.58(18) . . ?
F4 C24 F3 108.12(18) . . ?
F4 C24 F5 108.75(19) . . ?
F4 C24 C23 111.39(19) . . ?
F5 C24 F3 107.8(2) . . ?
F5 C24 C23 110.14(19) . . ?

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 C7 C8 C9 -179.96(17) . . . . ?
P1 C7 C12 C11 179.72(16) . . . . ?
P1 C13 C14 C15 179.24(15) . . . . ?
P1 C13 C16 O2 -179.53(14) . . . . ?
P1 C13 C16 C17 1.6(4) . . . . ?
F1 C23 C24 F3 176.34(18) . . . . ?
F1 C23 C24 F4 56.1(2) . . . . ?
F1 C23 C24 F5 -64.7(2) . . . . ?
F2 C23 C24 F3 61.7(2) . . . . ?
F2 C23 C24 F4 -58.6(2) . . . . ?
F2 C23 C24 F5 -179.33(17) . . . . ?
O1 P1 C6 C1 128.06(17) . . . . ?
O1 P1 C6 C5 -49.76(17) . . . . ?
O1 P1 C7 C8 -7.5(2) . . . . ?
O1 P1 C7 C12 171.08(16) . . . . ?
O1 P1 C13 C14 113.39(17) . . . . ?
O1 P1 C13 C16 -66.5(2) . . . . ?
O2 C15 C23 F1 -169.03(17) . . . . ?
O2 C15 C23 F2 -49.9(2) . . . . ?
O2 C15 C23 C24 71.7(2) . . . . ?
O2 C16 C17 C18 28.2(3) . . . . ?
O2 C16 C17 C22 -149.72(18) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C1 C6 P1 -176.12(15) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 P1 176.79(15) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C6 P1 C7 C8 -129.76(17) . . . . ?
C6 P1 C7 C12 48.8(2) . . . . ?
C6 P1 C13 C14 -121.06(18) . . . . ?
C6 P1 C13 C16 59.1(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C7 P1 C6 C1 -109.95(18) . . . . ?
C7 P1 C6 C5 72.23(17) . . . . ?
C7 P1 C13 C14 -9.8(2) . . . . ?
C7 P1 C13 C16 170.37(19) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C7 C12 C11 -1.7(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C7 0.9(3) . . . . ?
C12 C7 C8 C9 1.4(3) . . . . ?
C13 P1 C6 C1 1.0(2) . . . . ?
C13 P1 C6 C5 -176.84(14) . . . . ?
C13 P1 C7 C8 117.57(17) . . . . ?
C13 P1 C7 C12 -63.85(19) . . . . ?
C13 C14 C15 O2 0.9(2) . . . . ?
C13 C14 C15 C23 -177.8(2) . . . . ?
C13 C16 C17 C18 -153.0(2) . . . . ?
C13 C16 C17 C22 29.1(3) . . . . ?
C14 C13 C16 O2 0.6(2) . . . . ?
C14 C13 C16 C17 -178.3(2) . . . . ?
C14 C15 C23 F1 9.5(3) . . . . ?
C14 C15 C23 F2 128.7(2) . . . . ?
C14 C15 C23 C24 -109.7(3) . . . . ?
C15 O2 C16 C13 -0.1(2) . . . . ?
C15 O2 C16 C17 179.04(17) . . . . ?
C15 C23 C24 F3 -63.0(3) . . . . ?
C15 C23 C24 F4 176.79(18) . . . . ?
C15 C23 C24 F5 56.0(2) . . . . ?
C16 O2 C15 C14 -0.5(2) . . . . ?
C16 O2 C15 C23 178.36(17) . . . . ?
C16 C13 C14 C15 -0.9(2) . . . . ?
C16 C17 C18 C19 -176.15(18) . . . . ?
C16 C17 C22 C21 177.13(18) . . . . ?
C17 C18 C19 C20 -1.5(3) . . . . ?
C18 C17 C22 C21 -0.8(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C20 C21 C22 C17 -0.5(3) . . . . ?
C22 C17 C18 C19 1.8(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.702
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shuang
_database_code_depnum_ccdc_archive 'CCDC 2024117'
loop_
_audit_author_name
_audit_author_address
Xue-Qiang
;Nanjing Tech
China
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2023-02-04 downloaded from the CCDC.
;
_audit_creation_date             2020-08-19
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H25 F5 O3 P2'
_chemical_formula_sum            'C36 H25 F5 O3 P2'
_chemical_formula_weight         662.50
_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 0.0033 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'
F F 0.0171 0.0103 '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                   11.3450(6)
_cell_length_b                   12.0953(6)
_cell_length_c                   14.1162(7)
_cell_angle_alpha                89.245(4)
_cell_angle_beta                 77.498(4)
_cell_angle_gamma                62.787(5)
_cell_volume                     1673.56(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7374
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.1460
_cell_measurement_theta_min      2.9510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60556
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14757
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.063
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  57.00   1.00    1.20    --  -11.43  57.00 150.00   96
  2  ω    -75.00  19.00   1.00    1.20    --  -11.43 -77.00-120.00   94
  3  ω    -19.00   7.00   1.00    1.20    --   12.05 -99.00-180.00   26
  4  ω    -83.00  17.00   1.00    1.20    --  -11.43 -57.00   0.00  100
  5  ω    -20.00   5.00   1.00    1.20    --  -11.27 -99.00-180.00   25
  6  ω    -20.00   5.00   1.00    4.00    --  -11.35 -99.00-180.00   25
  7  ω    -12.00  13.00   1.00    4.00    --  -11.35 -37.00-180.00   25
  8  ω    -12.00  13.00   1.00    8.00    --  -11.27 -37.00  90.00   25
;
_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      0.0498565000
_diffrn_orient_matrix_UB_12      -0.0137178000
_diffrn_orient_matrix_UB_13      0.0273201000
_diffrn_orient_matrix_UB_21      -0.0239526000
_diffrn_orient_matrix_UB_22      0.0648303000
_diffrn_orient_matrix_UB_23      0.0110713000
_diffrn_orient_matrix_UB_31      -0.0466508000
_diffrn_orient_matrix_UB_32      -0.0000996000
_diffrn_orient_matrix_UB_33      0.0424981000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4577
_reflns_number_total             5685
_reflns_odcompleteness_completeness 95.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5685
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.068
_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)+(0.1015P)²+0.3064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1719
_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), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
;
_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 0.89948(6) 0.45053(6) 0.78302(5) 0.0192(2) Uani 1 1 d . . . . .
P2 P 0.59937(6) 0.76790(6) 0.78874(5) 0.0223(2) Uani 1 1 d . . . . .
F1 F 0.46339(15) 0.61273(15) 0.56390(15) 0.0416(5) Uani 1 1 d . . . . .
F2 F 0.40329(14) 0.77010(15) 0.66822(13) 0.0370(4) Uani 1 1 d . . . . .
F3 F 0.5230(2) 0.86908(19) 0.52989(18) 0.0611(6) Uani 1 1 d . . . . .
F4 F 0.38247(17) 0.82307(18) 0.48403(17) 0.0546(5) Uani 1 1 d . . . . .
F5 F 0.5981(2) 0.7065(2) 0.43003(16) 0.0719(7) Uani 1 1 d . . . . .
O1 O 0.79741(16) 0.48528(15) 0.87783(14) 0.0246(4) Uani 1 1 d . . . . .
O2 O 0.72007(16) 0.51841(16) 0.56058(14) 0.0244(4) Uani 1 1 d . . . . .
O3 O 0.54917(18) 0.88081(16) 0.73481(15) 0.0314(5) Uani 1 1 d . . . . .
C1 C 1.0257(2) 0.5015(2) 0.7793(2) 0.0218(6) Uani 1 1 d . . . . .
C2 C 1.0834(3) 0.5405(3) 0.6963(2) 0.0288(6) Uani 1 1 d . . . . .
H2 H 1.053820 0.544623 0.639241 0.035 Uiso 1 1 calc R U . . .
C3 C 1.1845(3) 0.5729(3) 0.6998(2) 0.0332(7) Uani 1 1 d . . . . .
H3 H 1.223709 0.598173 0.644723 0.040 Uiso 1 1 calc R U . . .
C4 C 1.2278(3) 0.5679(3) 0.7849(2) 0.0353(7) Uani 1 1 d . . . . .
H4 H 1.295373 0.590539 0.786882 0.042 Uiso 1 1 calc R U . . .
C5 C 1.1712(3) 0.5293(3) 0.8669(2) 0.0313(7) Uani 1 1 d . . . . .
H5 H 1.200710 0.525552 0.923955 0.038 Uiso 1 1 calc R U . . .
C6 C 1.0701(2) 0.4961(2) 0.8637(2) 0.0257(6) Uani 1 1 d . . . . .
H6 H 1.032005 0.469961 0.918797 0.031 Uiso 1 1 calc R U . . .
C7 C 0.9924(2) 0.2825(2) 0.7550(2) 0.0219(6) Uani 1 1 d . . . . .
C8 C 0.9150(3) 0.2201(2) 0.7584(2) 0.0277(6) Uani 1 1 d . . . . .
H8 H 0.820768 0.265240 0.768232 0.033 Uiso 1 1 calc R U . . .
C9 C 0.9782(3) 0.0905(3) 0.7471(2) 0.0335(7) Uani 1 1 d . . . . .
H9 H 0.926503 0.048719 0.748378 0.040 Uiso 1 1 calc R U . . .
C10 C 1.1179(3) 0.0237(3) 0.7339(3) 0.0386(8) Uani 1 1 d . . . . .
H10 H 1.159931 -0.063111 0.727632 0.046 Uiso 1 1 calc R U . . .
C11 C 1.1956(3) 0.0851(3) 0.7301(2) 0.0345(7) Uani 1 1 d . . . . .
H11 H 1.289818 0.039564 0.720521 0.041 Uiso 1 1 calc R U . . .
C12 C 1.1328(2) 0.2149(2) 0.7404(2) 0.0285(6) Uani 1 1 d . . . . .
H12 H 1.185020 0.256403 0.737587 0.034 Uiso 1 1 calc R U . . .
C13 C 0.9276(2) 0.3322(2) 0.5448(2) 0.0224(6) Uani 1 1 d . . . . .
C14 C 0.8785(3) 0.2573(2) 0.5100(2) 0.0288(6) Uani 1 1 d . . . . .
H14 H 0.785084 0.284453 0.522943 0.035 Uiso 1 1 calc R U . . .
C15 C 0.9676(3) 0.1438(3) 0.4566(2) 0.0348(7) Uani 1 1 d . . . . .
H15 H 0.934302 0.094514 0.433923 0.042 Uiso 1 1 calc R U . . .
C16 C 1.1069(3) 0.1035(3) 0.4370(2) 0.0367(7) Uani 1 1 d . . . . .
H16 H 1.167079 0.026382 0.401817 0.044 Uiso 1 1 calc R U . . .
C17 C 1.1567(3) 0.1767(3) 0.4692(2) 0.0372(8) Uani 1 1 d . . . . .
H17 H 1.250191 0.149612 0.455011 0.045 Uiso 1 1 calc R U . . .
C18 C 1.0672(2) 0.2915(2) 0.5231(2) 0.0262(6) Uani 1 1 d . . . . .
H18 H 1.101131 0.340920 0.544691 0.031 Uiso 1 1 calc R U . . .
C19 C 0.8292(2) 0.4520(2) 0.6009(2) 0.0219(6) Uani 1 1 d . . . . .
C20 C 0.8127(2) 0.5141(2) 0.68703(19) 0.0184(5) Uani 1 1 d . . . . .
C21 C 0.6844(2) 0.6304(2) 0.6999(2) 0.0208(6) Uani 1 1 d . . . . .
C22 C 0.6343(2) 0.6244(2) 0.6220(2) 0.0235(6) Uani 1 1 d . . . . .
C23 C 0.7124(2) 0.7717(2) 0.8592(2) 0.0246(6) Uani 1 1 d . . . . .
C24 C 0.6908(3) 0.7591(2) 0.9578(2) 0.0312(7) Uani 1 1 d . . . . .
H24 H 0.624731 0.736209 0.987444 0.037 Uiso 1 1 calc R U . . .
C25 C 0.7671(3) 0.7803(3) 1.0131(3) 0.0377(7) Uani 1 1 d . . . . .
H25 H 0.750929 0.773414 1.079810 0.045 Uiso 1 1 calc R U . . .
C26 C 0.8670(3) 0.8116(3) 0.9686(3) 0.0405(8) Uani 1 1 d . . . . .
H26 H 0.919500 0.824346 1.005278 0.049 Uiso 1 1 calc R U . . .
C27 C 0.8894(3) 0.8240(3) 0.8703(3) 0.0408(8) Uani 1 1 d . . . . .
H27 H 0.957261 0.844764 0.840882 0.049 Uiso 1 1 calc R U . . .
C28 C 0.8120(3) 0.8059(2) 0.8147(2) 0.0322(7) Uani 1 1 d . . . . .
H28 H 0.826022 0.816445 0.748571 0.039 Uiso 1 1 calc R U . . .
C29 C 0.4639(2) 0.7523(2) 0.8716(2) 0.0241(6) Uani 1 1 d . . . . .
C30 C 0.4759(2) 0.6374(2) 0.8987(2) 0.0263(6) Uani 1 1 d . . . . .
H30 H 0.556651 0.564678 0.874696 0.032 Uiso 1 1 calc R U . . .
C31 C 0.3674(2) 0.6317(3) 0.9613(2) 0.0284(6) Uani 1 1 d . . . . .
H31 H 0.375248 0.554869 0.979483 0.034 Uiso 1 1 calc R U . . .
C32 C 0.2472(3) 0.7397(3) 0.9969(2) 0.0324(7) Uani 1 1 d . . . . .
H32 H 0.174072 0.735178 1.038437 0.039 Uiso 1 1 calc R U . . .
C33 C 0.2353(3) 0.8534(3) 0.9713(3) 0.0395(8) Uani 1 1 d . . . . .
H33 H 0.154592 0.925828 0.996165 0.047 Uiso 1 1 calc R U . . .
C34 C 0.3436(3) 0.8609(3) 0.9082(2) 0.0367(8) Uani 1 1 d . . . . .
H34 H 0.335482 0.938056 0.890777 0.044 Uiso 1 1 calc R U . . .
C35 C 0.5024(2) 0.6961(2) 0.5916(2) 0.0293(7) Uani 1 1 d . . . . .
C36 C 0.5021(3) 0.7750(3) 0.5065(3) 0.0380(8) 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 1.4858(18) . ?
P1 C1 1.791(2) . ?
P1 C7 1.810(2) . ?
P1 C20 1.804(3) . ?
P2 O3 1.489(2) . ?
P2 C21 1.825(3) . ?
P2 C23 1.801(3) . ?
P2 C29 1.802(3) . ?
F1 C35 1.363(3) . ?
F2 C35 1.347(3) . ?
F3 C36 1.323(4) . ?
F4 C36 1.319(3) . ?
F5 C36 1.314(4) . ?
O2 C19 1.373(3) . ?
O2 C22 1.366(3) . ?
C1 C2 1.399(4) . ?
C1 C6 1.381(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(4) . ?
C7 C12 1.386(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.400(4) . ?
C13 C18 1.387(3) . ?
C13 C19 1.464(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.393(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(4) . ?
C20 C21 1.466(3) . ?
C21 C22 1.360(4) . ?
C22 C35 1.502(4) . ?
C23 C24 1.379(4) . ?
C23 C28 1.399(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.379(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.375(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.383(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.389(4) . ?
C29 C34 1.389(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.380(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.382(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.371(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.391(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.525(4) . ?

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 114.00(11) . . ?
O1 P1 C7 110.88(11) . . ?
O1 P1 C20 109.31(11) . . ?
C1 P1 C7 105.99(11) . . ?
C1 P1 C20 109.13(12) . . ?
C20 P1 C7 107.28(12) . . ?
O3 P2 C21 108.02(12) . . ?
O3 P2 C23 110.80(12) . . ?
O3 P2 C29 113.08(11) . . ?
C23 P2 C21 111.48(11) . . ?
C23 P2 C29 107.32(13) . . ?
C29 P2 C21 106.09(11) . . ?
C22 O2 C19 106.9(2) . . ?
C2 C1 P1 124.0(2) . . ?
C6 C1 P1 116.15(19) . . ?
C6 C1 C2 119.8(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.7(3) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 P1 116.73(18) . . ?
C12 C7 P1 123.2(2) . . ?
C12 C7 C8 119.7(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.0(2) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C19 118.6(2) . . ?
C18 C13 C14 119.0(2) . . ?
C18 C13 C19 122.4(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.2(3) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
O2 C19 C13 113.1(2) . . ?
C20 C19 O2 110.1(2) . . ?
C20 C19 C13 136.7(2) . . ?
C19 C20 P1 127.28(19) . . ?
C19 C20 C21 106.3(2) . . ?
C21 C20 P1 124.21(19) . . ?
C20 C21 P2 133.4(2) . . ?
C22 C21 P2 121.63(18) . . ?
C22 C21 C20 104.8(2) . . ?
O2 C22 C35 111.3(2) . . ?
C21 C22 O2 111.8(2) . . ?
C21 C22 C35 136.5(2) . . ?
C24 C23 P2 121.62(19) . . ?
C24 C23 C28 119.7(3) . . ?
C28 C23 P2 118.0(2) . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.4(3) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.7(3) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.2(3) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 119.6 . . ?
C26 C27 C28 120.7(3) . . ?
C28 C27 H27 119.6 . . ?
C23 C28 H28 120.4 . . ?
C27 C28 C23 119.2(3) . . ?
C27 C28 H28 120.4 . . ?
C30 C29 P2 122.63(19) . . ?
C34 C29 P2 117.4(2) . . ?
C34 C29 C30 120.0(2) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.8(2) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.2(2) . . ?
C32 C31 H31 119.9 . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.3(2) . . ?
C33 C32 H32 119.9 . . ?
C32 C33 H33 119.9 . . ?
C32 C33 C34 120.3(3) . . ?
C34 C33 H33 119.9 . . ?
C29 C34 C33 119.5(3) . . ?
C29 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
F1 C35 C22 108.2(2) . . ?
F1 C35 C36 105.6(3) . . ?
F2 C35 F1 106.40(19) . . ?
F2 C35 C22 110.1(3) . . ?
F2 C35 C36 108.2(2) . . ?
C22 C35 C36 117.7(2) . . ?
F3 C36 C35 110.7(3) . . ?
F4 C36 F3 107.5(2) . . ?
F4 C36 C35 109.9(2) . . ?
F5 C36 F3 108.9(3) . . ?
F5 C36 F4 109.5(3) . . ?
F5 C36 C35 110.3(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 -177.1(2) . . . . ?
P1 C1 C6 C5 177.7(2) . . . . ?
P1 C7 C8 C9 -173.8(2) . . . . ?
P1 C7 C12 C11 172.8(2) . . . . ?
P1 C20 C21 P2 22.2(3) . . . . ?
P1 C20 C21 C22 -162.00(17) . . . . ?
P2 C21 C22 O2 174.47(16) . . . . ?
P2 C21 C22 C35 -14.2(4) . . . . ?
P2 C23 C24 C25 -170.6(2) . . . . ?
P2 C23 C28 C27 172.4(2) . . . . ?
P2 C29 C30 C31 -178.9(2) . . . . ?
P2 C29 C34 C33 179.0(3) . . . . ?
F1 C35 C36 F3 172.6(2) . . . . ?
F1 C35 C36 F4 54.0(3) . . . . ?
F1 C35 C36 F5 -66.8(3) . . . . ?
F2 C35 C36 F3 59.0(3) . . . . ?
F2 C35 C36 F4 -59.6(3) . . . . ?
F2 C35 C36 F5 179.6(2) . . . . ?
O1 P1 C1 C2 -145.2(2) . . . . ?
O1 P1 C1 C6 37.4(2) . . . . ?
O1 P1 C7 C8 52.6(3) . . . . ?
O1 P1 C7 C12 -120.8(2) . . . . ?
O1 P1 C20 C19 -129.9(2) . . . . ?
O1 P1 C20 C21 30.9(2) . . . . ?
O2 C19 C20 P1 161.85(16) . . . . ?
O2 C19 C20 C21 -1.7(3) . . . . ?
O2 C22 C35 F1 41.2(3) . . . . ?
O2 C22 C35 F2 157.1(2) . . . . ?
O2 C22 C35 C36 -78.2(3) . . . . ?
O3 P2 C21 C20 135.7(2) . . . . ?
O3 P2 C21 C22 -39.6(2) . . . . ?
O3 P2 C23 C24 126.1(2) . . . . ?
O3 P2 C23 C28 -44.7(2) . . . . ?
O3 P2 C29 C30 153.1(2) . . . . ?
O3 P2 C29 C34 -26.4(3) . . . . ?
C1 P1 C7 C8 176.8(2) . . . . ?
C1 P1 C7 C12 3.4(3) . . . . ?
C1 P1 C20 C19 104.8(2) . . . . ?
C1 P1 C20 C21 -94.4(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C7 P1 C1 C2 92.5(2) . . . . ?
C7 P1 C1 C6 -84.8(2) . . . . ?
C7 P1 C20 C19 -9.6(2) . . . . ?
C7 P1 C20 C21 151.21(19) . . . . ?
C7 C8 C9 C10 1.0(5) . . . . ?
C8 C7 C12 C11 -0.5(4) . . . . ?
C8 C9 C10 C11 -1.2(5) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C7 0.2(5) . . . . ?
C12 C7 C8 C9 -0.1(4) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C13 C19 C20 P1 -13.8(4) . . . . ?
C13 C19 C20 C21 -177.4(3) . . . . ?
C14 C13 C18 C17 -1.3(4) . . . . ?
C14 C13 C19 O2 -44.2(3) . . . . ?
C14 C13 C19 C20 131.4(3) . . . . ?
C14 C15 C16 C17 -0.9(5) . . . . ?
C15 C16 C17 C18 0.9(5) . . . . ?
C16 C17 C18 C13 0.2(5) . . . . ?
C18 C13 C14 C15 1.3(4) . . . . ?
C18 C13 C19 O2 134.4(3) . . . . ?
C18 C13 C19 C20 -50.1(4) . . . . ?
C19 O2 C22 C21 1.0(3) . . . . ?
C19 O2 C22 C35 -172.6(2) . . . . ?
C19 C13 C14 C15 179.8(3) . . . . ?
C19 C13 C18 C17 -179.8(3) . . . . ?
C19 C20 C21 P2 -173.61(19) . . . . ?
C19 C20 C21 C22 2.2(3) . . . . ?
C20 P1 C1 C2 -22.7(3) . . . . ?
C20 P1 C1 C6 159.93(19) . . . . ?
C20 P1 C7 C8 -66.7(2) . . . . ?
C20 P1 C7 C12 119.9(2) . . . . ?
C20 C21 C22 O2 -2.0(3) . . . . ?
C20 C21 C22 C35 169.3(3) . . . . ?
C21 P2 C23 C24 -113.5(2) . . . . ?
C21 P2 C23 C28 75.6(2) . . . . ?
C21 P2 C29 C30 34.9(3) . . . . ?
C21 P2 C29 C34 -144.6(2) . . . . ?
C21 C22 C35 F1 -130.1(3) . . . . ?
C21 C22 C35 F2 -14.2(4) . . . . ?
C21 C22 C35 C36 110.4(4) . . . . ?
C22 O2 C19 C13 177.29(19) . . . . ?
C22 O2 C19 C20 0.6(3) . . . . ?
C22 C35 C36 F3 -66.6(3) . . . . ?
C22 C35 C36 F4 174.8(2) . . . . ?
C22 C35 C36 F5 54.0(4) . . . . ?
C23 P2 C21 C20 13.7(3) . . . . ?
C23 P2 C21 C22 -161.6(2) . . . . ?
C23 P2 C29 C30 -84.4(3) . . . . ?
C23 P2 C29 C34 96.1(3) . . . . ?
C23 C24 C25 C26 -1.4(4) . . . . ?
C24 C23 C28 C27 1.4(4) . . . . ?
C24 C25 C26 C27 1.2(4) . . . . ?
C25 C26 C27 C28 0.3(4) . . . . ?
C26 C27 C28 C23 -1.6(4) . . . . ?
C28 C23 C24 C25 0.1(4) . . . . ?
C29 P2 C21 C20 -102.8(2) . . . . ?
C29 P2 C21 C22 81.9(2) . . . . ?
C29 P2 C23 C24 2.2(2) . . . . ?
C29 P2 C23 C28 -168.6(2) . . . . ?
C29 C30 C31 C32 0.1(5) . . . . ?
C30 C29 C34 C33 -0.6(5) . . . . ?
C30 C31 C32 C33 -0.8(5) . . . . ?
C31 C32 C33 C34 0.8(5) . . . . ?
C32 C33 C34 C29 -0.1(5) . . . . ?
C34 C29 C30 C31 0.6(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 1.000 0.000 242.2 52.6 ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.462
_oxdiff_exptl_absorpt_empirical_full_min 0.593
