# 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_8362
_database_code_depnum_ccdc_archive 'CCDC 2131663'
loop_
_audit_author_name
_audit_author_address
cxq
;Nanjing Tech University
China
;
_audit_update_record             
;
2021-12-30 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_audit_creation_date             2021-11-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H21 F2 O2 P'
_chemical_formula_sum            'C28 H21 F2 O2 P'
_chemical_formula_weight         458.42
_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                   6.1385(4)
_cell_length_b                   11.7600(8)
_cell_length_c                   17.0258(11)
_cell_angle_alpha                104.208(6)
_cell_angle_beta                 96.087(5)
_cell_angle_gamma                103.597(6)
_cell_volume                     1140.47(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3164
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.8450
_cell_measurement_theta_min      3.4550
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70484
_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    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.927
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(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 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  34.00   1.00    1.20    --   11.90 -57.00-150.00   89
  2  ω    -15.00  78.00   1.00    1.20    --   11.90  77.00 120.00   93
  3  ω    -16.00  85.00   1.00    1.20    --   11.90  57.00   0.00  101
;
_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      0.0390788000
_diffrn_orient_matrix_UB_12      0.0574407000
_diffrn_orient_matrix_UB_13      0.0299917000
_diffrn_orient_matrix_UB_21      -0.0278778000
_diffrn_orient_matrix_UB_22      -0.0284356000
_diffrn_orient_matrix_UB_23      0.0312114000
_diffrn_orient_matrix_UB_31      0.1107626000
_diffrn_orient_matrix_UB_32      -0.0083409000
_diffrn_orient_matrix_UB_33      0.0055393000
_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                3269
_reflns_number_total             4016
_reflns_odcompleteness_completeness 99.96
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4016
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.047
_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)+(0.0418P)²+0.2532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1041
_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), 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 0.15806(9) 0.68786(4) 0.71389(3) 0.01845(15) Uani 1 1 d . . . . .
F1 F -0.0203(2) 1.05871(11) 0.94491(7) 0.0408(4) Uani 1 1 d . . . . .
F2 F -0.0534(2) 1.13163(11) 0.84184(7) 0.0342(3) Uani 1 1 d . . . . .
O1 O 0.3699(2) 0.79233(11) 0.77302(7) 0.0198(3) Uani 1 1 d . . . . .
O2 O -0.0681(2) 0.70427(12) 0.72507(8) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.4729(3) 0.77193(17) 0.90931(12) 0.0225(5) Uani 1 1 d . . . . .
C2 C 0.3985(4) 0.75997(19) 0.98192(12) 0.0290(5) Uani 1 1 d . . . . .
H2 H 0.280479 0.792167 0.998143 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4974(4) 0.7011(2) 1.03000(13) 0.0356(6) Uani 1 1 d . . . . .
H3 H 0.446646 0.694300 1.078643 0.043 Uiso 1 1 calc R U . . .
C4 C 0.6714(4) 0.6521(2) 1.00649(14) 0.0387(6) Uani 1 1 d . . . . .
H4 H 0.736224 0.611044 1.038634 0.046 Uiso 1 1 calc R U . . .
C5 C 0.7485(4) 0.6642(2) 0.93527(13) 0.0358(6) Uani 1 1 d . . . . .
H5 H 0.867521 0.632315 0.919821 0.043 Uiso 1 1 calc R U . . .
C6 C 0.6509(4) 0.72348(19) 0.88637(13) 0.0278(5) Uani 1 1 d . . . . .
H6 H 0.703901 0.731005 0.838206 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3653(3) 0.83432(17) 0.85726(11) 0.0213(4) Uani 1 1 d . . . . .
C8 C 0.2756(4) 0.92598(18) 0.88432(12) 0.0244(5) Uani 1 1 d . . . . .
H8 H 0.281277 0.950793 0.940916 0.029 Uiso 1 1 calc R U . . .
C9 C 0.1692(3) 0.99310(17) 0.83700(12) 0.0229(5) Uani 1 1 d . . . . .
C10 C 0.0388(4) 1.05644(18) 0.87218(12) 0.0265(5) Uani 1 1 d . . . . .
C11 C 0.2174(3) 1.00327(17) 0.75470(12) 0.0229(5) Uani 1 1 d . . . . .
C12 C 0.0435(4) 0.97418(19) 0.68844(13) 0.0297(5) Uani 1 1 d . . . . .
H12 H -0.106405 0.944330 0.694285 0.036 Uiso 1 1 calc R U . . .
C13 C 0.0917(5) 0.9893(2) 0.61353(14) 0.0404(6) Uani 1 1 d . . . . .
H13 H -0.026131 0.969469 0.569236 0.048 Uiso 1 1 calc R U . . .
C14 C 0.3122(5) 1.0334(2) 0.60413(14) 0.0422(6) Uani 1 1 d . . . . .
H14 H 0.343735 1.043602 0.553674 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4861(4) 1.0624(2) 0.66952(15) 0.0404(6) Uani 1 1 d . . . . .
H15 H 0.635750 1.092218 0.663351 0.049 Uiso 1 1 calc R U . . .
C16 C 0.4391(4) 1.04727(19) 0.74434(14) 0.0316(5) Uani 1 1 d . . . . .
H16 H 0.557725 1.066877 0.788329 0.038 Uiso 1 1 calc R U . . .
C17 C 0.2283(3) 0.69465(17) 0.61548(11) 0.0194(4) Uani 1 1 d . . . . .
C18 C 0.0473(4) 0.66497(18) 0.55099(12) 0.0270(5) Uani 1 1 d . . . . .
H18 H -0.101252 0.640843 0.560027 0.032 Uiso 1 1 calc R U . . .
C19 C 0.0867(4) 0.6711(2) 0.47377(13) 0.0360(6) Uani 1 1 d . . . . .
H19 H -0.034780 0.651440 0.430801 0.043 Uiso 1 1 calc R U . . .
C20 C 0.3067(4) 0.7065(2) 0.46055(13) 0.0375(6) Uani 1 1 d . . . . .
H20 H 0.333502 0.711660 0.408625 0.045 Uiso 1 1 calc R U . . .
C21 C 0.4871(4) 0.7342(2) 0.52356(14) 0.0368(6) Uani 1 1 d . . . . .
H21 H 0.635246 0.757013 0.513869 0.044 Uiso 1 1 calc R U . . .
C22 C 0.4492(4) 0.72823(19) 0.60143(13) 0.0276(5) Uani 1 1 d . . . . .
H22 H 0.571395 0.746681 0.643952 0.033 Uiso 1 1 calc R U . . .
C23 C 0.1864(3) 0.54695(16) 0.73076(11) 0.0179(4) Uani 1 1 d . . . . .
C24 C 0.3740(4) 0.50264(18) 0.71410(12) 0.0250(5) Uani 1 1 d . . . . .
H24 H 0.492764 0.547864 0.695459 0.030 Uiso 1 1 calc R U . . .
C25 C 0.3815(4) 0.39138(18) 0.72551(13) 0.0276(5) Uani 1 1 d . . . . .
H25 H 0.504856 0.361103 0.713585 0.033 Uiso 1 1 calc R U . . .
C26 C 0.2086(4) 0.32486(19) 0.75432(13) 0.0317(5) Uani 1 1 d . . . . .
H26 H 0.215412 0.250041 0.761915 0.038 Uiso 1 1 calc R U . . .
C27 C 0.0247(4) 0.3690(2) 0.77199(14) 0.0334(5) Uani 1 1 d . . . . .
H27 H -0.091646 0.324304 0.792005 0.040 Uiso 1 1 calc R U . . .
C28 C 0.0137(4) 0.47940(18) 0.75993(12) 0.0264(5) Uani 1 1 d . . . . .
H28 H -0.110949 0.508658 0.771509 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.6056(14) . ?
P1 O2 1.4712(13) . ?
P1 C17 1.7894(19) . ?
P1 C23 1.7937(18) . ?
F1 C10 1.323(2) . ?
F2 C10 1.329(2) . ?
O1 C7 1.403(2) . ?
C1 C2 1.390(3) . ?
C1 C6 1.395(3) . ?
C1 C7 1.477(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.329(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.464(3) . ?
C9 C10 1.310(3) . ?
C9 C11 1.490(3) . ?
C11 C12 1.383(3) . ?
C11 C16 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.390(3) . ?
C17 C22 1.384(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.399(3) . ?
C23 C28 1.383(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.380(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.374(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.380(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.379(3) . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C17 100.15(8) . . ?
O1 P1 C23 106.12(8) . . ?
O2 P1 O1 115.52(8) . . ?
O2 P1 C17 114.10(8) . . ?
O2 P1 C23 111.17(9) . . ?
C17 P1 C23 108.97(8) . . ?
C7 O1 P1 119.87(12) . . ?
C2 C1 C6 118.66(17) . . ?
C2 C1 C7 120.75(17) . . ?
C6 C1 C7 120.59(17) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.75(19) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.64(19) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C1 114.57(15) . . ?
C8 C7 O1 119.89(16) . . ?
C8 C7 C1 125.50(18) . . ?
C7 C8 H8 115.7 . . ?
C7 C8 C9 128.69(18) . . ?
C9 C8 H8 115.7 . . ?
C8 C9 C11 123.93(17) . . ?
C10 C9 C8 117.84(18) . . ?
C10 C9 C11 117.96(17) . . ?
F1 C10 F2 107.98(15) . . ?
C9 C10 F1 125.98(17) . . ?
C9 C10 F2 126.03(18) . . ?
C12 C11 C9 121.31(19) . . ?
C12 C11 C16 118.73(19) . . ?
C16 C11 C9 119.91(18) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.7(2) . . ?
C15 C16 H16 119.6 . . ?
C18 C17 P1 116.75(15) . . ?
C22 C17 P1 123.60(15) . . ?
C22 C17 C18 119.65(18) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 119.5(2) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C24 C23 P1 122.39(15) . . ?
C28 C23 P1 118.28(14) . . ?
C28 C23 C24 119.32(17) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.54(19) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.62(19) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.08(19) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.1 . . ?
C28 C27 C26 119.9(2) . . ?
C28 C27 H27 120.1 . . ?
C23 C28 H28 119.7 . . ?
C27 C28 C23 120.53(18) . . ?
C27 C28 H28 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C7 C1 93.47(18) . . . . ?
P1 O1 C7 C8 -88.6(2) . . . . ?
P1 C17 C18 C19 178.25(15) . . . . ?
P1 C17 C22 C21 -178.20(16) . . . . ?
P1 C23 C24 C25 -177.58(15) . . . . ?
P1 C23 C28 C27 178.39(16) . . . . ?
O1 P1 C17 C18 -149.29(15) . . . . ?
O1 P1 C17 C22 30.19(17) . . . . ?
O1 P1 C23 C24 -61.74(17) . . . . ?
O1 P1 C23 C28 119.42(16) . . . . ?
O1 C7 C8 C9 1.5(4) . . . . ?
O2 P1 O1 C7 45.46(14) . . . . ?
O2 P1 C17 C18 -25.27(18) . . . . ?
O2 P1 C17 C22 154.21(15) . . . . ?
O2 P1 C23 C24 171.91(15) . . . . ?
O2 P1 C23 C28 -6.93(18) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C7 C8 C9 179.2(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C2 C1 C7 O1 -150.51(18) . . . . ?
C2 C1 C7 C8 31.7(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C1 C7 O1 29.3(3) . . . . ?
C6 C1 C7 C8 -148.5(2) . . . . ?
C7 C1 C2 C3 179.5(2) . . . . ?
C7 C1 C6 C5 -179.4(2) . . . . ?
C7 C8 C9 C10 161.8(2) . . . . ?
C7 C8 C9 C11 -24.3(4) . . . . ?
C8 C9 C10 F1 -5.4(3) . . . . ?
C8 C9 C10 F2 173.16(19) . . . . ?
C8 C9 C11 C12 127.6(2) . . . . ?
C8 C9 C11 C16 -55.0(3) . . . . ?
C9 C11 C12 C13 177.22(18) . . . . ?
C9 C11 C16 C15 -177.14(18) . . . . ?
C10 C9 C11 C12 -58.4(3) . . . . ?
C10 C9 C11 C16 118.9(2) . . . . ?
C11 C9 C10 F1 -179.67(19) . . . . ?
C11 C9 C10 F2 -1.2(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C11 C16 C15 0.3(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C16 C11 C12 C13 -0.1(3) . . . . ?
C17 P1 O1 C7 168.50(12) . . . . ?
C17 P1 C23 C24 45.31(19) . . . . ?
C17 P1 C23 C28 -133.52(16) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C17 C22 C21 1.3(3) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 C22 -0.8(3) . . . . ?
C20 C21 C22 C17 -0.3(3) . . . . ?
C22 C17 C18 C19 -1.3(3) . . . . ?
C23 P1 O1 C7 -78.21(13) . . . . ?
C23 P1 C17 C18 99.62(16) . . . . ?
C23 P1 C17 C22 -80.89(18) . . . . ?
C23 C24 C25 C26 -1.1(3) . . . . ?
C24 C23 C28 C27 -0.5(3) . . . . ?
C24 C25 C26 C27 0.1(3) . . . . ?
C25 C26 C27 C28 0.6(3) . . . . ?
C26 C27 C28 C23 -0.5(3) . . . . ?
C28 C23 C24 C25 1.2(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 1.324
_oxdiff_exptl_absorpt_empirical_full_min 0.634
####################################################################### 
# 
# 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_862
_database_code_depnum_ccdc_archive 'CCDC 2249356'
loop_
_audit_author_name
_audit_author_address
cxq
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_audit_creation_date             2023-03-17
_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         'C36 H26 F2 N3 O4 P'
_chemical_formula_sum            'C36 H26 F2 N3 O4 P'
_chemical_formula_weight         633.57
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.6060(3)
_cell_length_b                   16.1758(4)
_cell_length_c                   14.0833(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.198(2)
_cell_angle_gamma                90
_cell_volume                     3067.89(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6919
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      74.0360
_cell_measurement_theta_min      4.1490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60786
_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    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       16
_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       -17
_diffrn_reflns_number            12151
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.167
_diffrn_reflns_theta_min         4.187
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(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 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  69.00   1.00    1.00    --   40.92  77.00 -90.00   57
  2  ω    111.00 177.00   1.00    1.58    --  108.20  45.00 -90.00   66
  3  ω    107.00 133.00   1.00    1.58    --  108.20 101.00 101.00   26
  4  ω     47.00 135.00   1.00    1.58    --  108.20 -61.00  90.00   88
  5  ω     68.00 100.00   1.00    1.58    --  108.20 -94.00  60.00   32
  6  ω     36.00 121.00   1.00    1.58    --  108.20-125.00   0.00   85
  7  ω     53.00  79.00   1.00    1.00    --   40.92-125.00  60.00   26
  8  ω     26.00  52.00   1.00    1.58    --  108.20 -94.00  60.00   26
  9  ω     23.00  95.00   1.00    1.00    --   40.92-125.00-150.00   72
 10  ω     70.00 107.00   1.00    1.58    --  108.20 -94.00-180.00   37
 11  ω     36.00 110.00   1.00    1.58    --  108.20 -45.00-180.00   74
 12  ω   -112.00 -14.00   1.00    1.00    --  -40.92 -57.00 -60.00   98
;
_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      -0.0730273000
_diffrn_orient_matrix_UB_12      0.0595513000
_diffrn_orient_matrix_UB_13      -0.0592911000
_diffrn_orient_matrix_UB_21      0.0787629000
_diffrn_orient_matrix_UB_22      0.0690560000
_diffrn_orient_matrix_UB_23      0.0140519000
_diffrn_orient_matrix_UB_31      0.0394203000
_diffrn_orient_matrix_UB_32      -0.0275997000
_diffrn_orient_matrix_UB_33      -0.0921393000
_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                5303
_reflns_number_total             6063
_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         0.337
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00099(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6063
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.025
_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)+(0.0545P)²+0.9764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1131
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26),
  C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34),
 C35(H35), C36(H36)
;
_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 0.71050(3) 0.36327(3) 0.47021(3) 0.02913(12) Uani 1 1 d . . . . .
F1 F 0.55536(8) 0.59563(7) 0.31951(6) 0.0403(3) Uani 1 1 d . . . . .
F2 F 0.68022(8) 0.63099(7) 0.24885(7) 0.0428(3) Uani 1 1 d . . . . .
O1 O 0.58872(10) 0.63898(9) -0.06799(8) 0.0418(3) Uani 1 1 d . . . . .
O2 O 0.44468(11) 0.70117(9) 0.19841(9) 0.0476(3) Uani 1 1 d . . . . .
O3 O 0.78188(9) 0.36409(10) 0.40096(8) 0.0432(3) Uani 1 1 d . . . . .
O4 O 0.61359(8) 0.41970(7) 0.43833(7) 0.0281(2) Uani 1 1 d . . . . .
N1 N 0.58221(10) 0.57086(10) 0.07567(9) 0.0330(3) Uani 1 1 d . . . . .
N2 N 0.53559(10) 0.58756(9) 0.15825(9) 0.0315(3) Uani 1 1 d . . . . .
N3 N 0.50385(10) 0.68982(9) 0.05210(9) 0.0332(3) Uani 1 1 d . . . . .
C1 C 0.64873(12) 0.50395(11) 0.07599(11) 0.0317(3) Uani 1 1 d . . . . .
C2 C 0.68156(14) 0.47856(12) -0.00891(12) 0.0385(4) Uani 1 1 d . . . . .
H2 H 0.656631 0.504095 -0.068215 0.046 Uiso 1 1 calc R U . . .
C3 C 0.75077(16) 0.41580(13) -0.00541(14) 0.0452(5) Uani 1 1 d . . . . .
H3 H 0.773284 0.398056 -0.062905 0.054 Uiso 1 1 calc R U . . .
C4 C 0.78783(15) 0.37837(13) 0.08070(15) 0.0462(5) Uani 1 1 d . . . . .
H4 H 0.836579 0.336144 0.082434 0.055 Uiso 1 1 calc R U . . .
C5 C 0.75342(13) 0.40282(12) 0.16438(13) 0.0396(4) Uani 1 1 d . . . . .
H5 H 0.778003 0.376534 0.223317 0.048 Uiso 1 1 calc R U . . .
C6 C 0.68353(12) 0.46523(11) 0.16284(11) 0.0315(3) Uani 1 1 d . . . . .
C7 C 0.64250(11) 0.48828(11) 0.25394(10) 0.0305(3) Uani 1 1 d . . . . .
H7 H 0.696978 0.484694 0.309527 0.037 Uiso 1 1 calc R U . . .
C8 C 0.60362(12) 0.57555(11) 0.24585(11) 0.0320(4) Uani 1 1 d . . . . .
C9 C 0.48912(12) 0.66607(12) 0.14307(11) 0.0347(4) Uani 1 1 d . . . . .
C10 C 0.56259(12) 0.63376(11) 0.01041(11) 0.0329(4) Uani 1 1 d . . . . .
C11 C 0.46616(12) 0.76550(12) 0.00771(12) 0.0345(4) Uani 1 1 d . . . . .
C12 C 0.47351(14) 0.83789(13) 0.06075(14) 0.0424(4) Uani 1 1 d . . . . .
H12 H 0.505238 0.838036 0.125368 0.051 Uiso 1 1 calc R U . . .
C13 C 0.43399(16) 0.91001(14) 0.01834(17) 0.0515(5) Uani 1 1 d . . . . .
H13 H 0.436611 0.959658 0.054637 0.062 Uiso 1 1 calc R U . . .
C14 C 0.39071(15) 0.91009(15) -0.07662(17) 0.0546(6) Uani 1 1 d . . . . .
H14 H 0.364564 0.959923 -0.105704 0.065 Uiso 1 1 calc R U . . .
C15 C 0.38550(14) 0.83833(15) -0.12884(15) 0.0509(5) Uani 1 1 d . . . . .
H15 H 0.356658 0.839077 -0.194366 0.061 Uiso 1 1 calc R U . . .
C16 C 0.42180(13) 0.76450(13) -0.08728(13) 0.0408(4) Uani 1 1 d . . . . .
H16 H 0.416361 0.714521 -0.123073 0.049 Uiso 1 1 calc R U . . .
C17 C 0.55950(11) 0.43131(11) 0.27134(11) 0.0299(3) Uani 1 1 d . . . . .
H17 H 0.512314 0.416792 0.217548 0.036 Uiso 1 1 calc R U . . .
C18 C 0.54682(11) 0.39972(10) 0.35565(10) 0.0267(3) Uani 1 1 d . . . . .
C19 C 0.45853(11) 0.35284(10) 0.37322(11) 0.0282(3) Uani 1 1 d . . . . .
C20 C 0.42347(13) 0.36065(11) 0.46099(12) 0.0345(4) Uani 1 1 d . . . . .
H20 H 0.461075 0.390434 0.511859 0.041 Uiso 1 1 calc R U . . .
C21 C 0.33386(14) 0.32505(14) 0.47420(13) 0.0445(4) Uani 1 1 d . . . . .
H21 H 0.309959 0.330933 0.534014 0.053 Uiso 1 1 calc R U . . .
C22 C 0.27922(14) 0.28121(14) 0.40127(14) 0.0457(5) Uani 1 1 d . . . . .
H22 H 0.217135 0.257929 0.410356 0.055 Uiso 1 1 calc R U . . .
C23 C 0.31468(14) 0.27103(13) 0.31472(13) 0.0417(4) Uani 1 1 d . . . . .
H23 H 0.277419 0.239929 0.264806 0.050 Uiso 1 1 calc R U . . .
C24 C 0.40434(13) 0.30606(12) 0.30063(12) 0.0351(4) Uani 1 1 d . . . . .
H24 H 0.428989 0.298216 0.241469 0.042 Uiso 1 1 calc R U . . .
C25 C 0.66400(13) 0.26221(11) 0.48899(12) 0.0354(4) Uani 1 1 d . . . . .
C26 C 0.61784(15) 0.24428(13) 0.56836(15) 0.0448(4) Uani 1 1 d . . . . .
H26 H 0.612950 0.285260 0.615781 0.054 Uiso 1 1 calc R U . . .
C27 C 0.57890(19) 0.16578(16) 0.5777(2) 0.0666(7) Uani 1 1 d . . . . .
H27 H 0.547315 0.152525 0.631717 0.080 Uiso 1 1 calc R U . . .
C28 C 0.5865(2) 0.10684(15) 0.5074(3) 0.0807(10) Uani 1 1 d . . . . .
H28 H 0.559272 0.053339 0.513322 0.097 Uiso 1 1 calc R U . . .
C29 C 0.6331(2) 0.12483(15) 0.4291(2) 0.0722(8) Uani 1 1 d . . . . .
H29 H 0.637736 0.083828 0.381697 0.087 Uiso 1 1 calc R U . . .
C30 C 0.67255(17) 0.20171(13) 0.41973(15) 0.0511(5) Uani 1 1 d . . . . .
H30 H 0.705623 0.213918 0.366378 0.061 Uiso 1 1 calc R U . . .
C31 C 0.75466(12) 0.40837(10) 0.58432(11) 0.0305(3) Uani 1 1 d . . . . .
C32 C 0.85060(13) 0.38848(14) 0.62507(12) 0.0427(4) Uani 1 1 d . . . . .
H32 H 0.889620 0.352311 0.592610 0.051 Uiso 1 1 calc R U . . .
C33 C 0.88945(16) 0.42158(17) 0.71342(14) 0.0542(6) Uani 1 1 d . . . . .
H33 H 0.954891 0.407579 0.741818 0.065 Uiso 1 1 calc R U . . .
C34 C 0.83345(18) 0.47447(14) 0.75973(14) 0.0542(6) Uani 1 1 d . . . . .
H34 H 0.861054 0.498202 0.819307 0.065 Uiso 1 1 calc R U . . .
C35 C 0.7373(2) 0.49353(15) 0.72051(15) 0.0620(6) Uani 1 1 d . . . . .
H35 H 0.698253 0.529185 0.753606 0.074 Uiso 1 1 calc R U . . .
C36 C 0.69812(17) 0.46029(14) 0.63254(13) 0.0498(5) Uani 1 1 d . . . . .
H36 H 0.632012 0.473293 0.605244 0.060 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 O3 1.4712(12) . ?
P1 O4 1.6139(11) . ?
P1 C25 1.7861(19) . ?
P1 C31 1.7889(16) . ?
F1 C8 1.3442(18) . ?
F2 C8 1.3710(19) . ?
O1 C10 1.210(2) . ?
O2 C9 1.196(2) . ?
O4 C18 1.4085(18) . ?
N1 N2 1.4278(17) . ?
N1 C1 1.410(2) . ?
N1 C10 1.371(2) . ?
N2 C8 1.446(2) . ?
N2 C9 1.421(2) . ?
N3 C9 1.379(2) . ?
N3 C10 1.393(2) . ?
N3 C11 1.435(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.395(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 C7 1.517(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.506(3) . ?
C7 C17 1.505(2) . ?
C11 C12 1.385(3) . ?
C11 C16 1.387(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.371(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.326(2) . ?
C18 C19 1.471(2) . ?
C19 C20 1.393(2) . ?
C19 C24 1.395(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.376(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(3) . ?
C25 C30 1.398(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.389(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.389(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.378(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.369(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.387(2) . ?
C31 C36 1.381(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.388(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.371(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.381(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.386(3) . ?
C36 H36 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
O3 P1 O4 113.63(7) . . ?
O3 P1 C25 112.80(9) . . ?
O3 P1 C31 115.02(8) . . ?
O4 P1 C25 105.44(7) . . ?
O4 P1 C31 100.12(7) . . ?
C25 P1 C31 108.72(8) . . ?
C18 O4 P1 120.35(10) . . ?
C1 N1 N2 120.13(13) . . ?
C10 N1 N2 109.81(13) . . ?
C10 N1 C1 129.41(13) . . ?
N1 N2 C8 111.39(12) . . ?
C9 N2 N1 106.64(12) . . ?
C9 N2 C8 117.73(14) . . ?
C9 N3 C10 112.23(14) . . ?
C9 N3 C11 123.49(15) . . ?
C10 N3 C11 124.23(13) . . ?
C2 C1 N1 120.42(15) . . ?
C6 C1 N1 118.99(14) . . ?
C6 C1 C2 120.56(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.05(17) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.93(17) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.66(18) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.60(17) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 120.75(15) . . ?
C5 C6 C1 119.16(15) . . ?
C5 C6 C7 120.04(15) . . ?
C6 C7 H7 109.1 . . ?
C8 C7 C6 109.51(13) . . ?
C8 C7 H7 109.1 . . ?
C17 C7 C6 111.25(14) . . ?
C17 C7 H7 109.1 . . ?
C17 C7 C8 108.82(13) . . ?
F1 C8 F2 105.73(13) . . ?
F1 C8 N2 107.59(13) . . ?
F1 C8 C7 111.90(13) . . ?
F2 C8 N2 109.26(13) . . ?
F2 C8 C7 110.70(13) . . ?
N2 C8 C7 111.45(14) . . ?
O2 C9 N2 125.57(16) . . ?
O2 C9 N3 128.84(18) . . ?
N3 C9 N2 105.56(14) . . ?
O1 C10 N1 127.50(17) . . ?
O1 C10 N3 126.87(16) . . ?
N1 C10 N3 105.62(13) . . ?
C12 C11 N3 119.50(15) . . ?
C12 C11 C16 121.20(18) . . ?
C16 C11 N3 119.30(17) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.09(19) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 120.92(19) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 118.4(2) . . ?
C11 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C7 C17 H17 117.3 . . ?
C18 C17 C7 125.33(14) . . ?
C18 C17 H17 117.3 . . ?
O4 C18 C19 115.16(12) . . ?
C17 C18 O4 120.05(14) . . ?
C17 C18 C19 124.25(14) . . ?
C20 C19 C18 119.59(15) . . ?
C20 C19 C24 119.18(15) . . ?
C24 C19 C18 121.01(14) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.07(16) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.43(16) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.00(17) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.17(17) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 120.0 . . ?
C23 C24 C19 120.08(16) . . ?
C23 C24 H24 120.0 . . ?
C26 C25 P1 121.38(14) . . ?
C26 C25 C30 120.50(19) . . ?
C30 C25 P1 118.09(16) . . ?
C25 C26 H26 120.3 . . ?
C25 C26 C27 119.3(2) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 120.3 . . ?
C28 C27 C26 119.4(3) . . ?
C28 C27 H27 120.3 . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 121.0(2) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.1(2) . . ?
C30 C29 H29 120.0 . . ?
C25 C30 H30 120.1 . . ?
C29 C30 C25 119.7(2) . . ?
C29 C30 H30 120.1 . . ?
C32 C31 P1 116.93(14) . . ?
C36 C31 P1 123.40(14) . . ?
C36 C31 C32 119.67(16) . . ?
C31 C32 H32 120.1 . . ?
C31 C32 C33 119.82(19) . . ?
C33 C32 H32 120.1 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.0(2) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 119.7 . . ?
C33 C34 C35 120.55(18) . . ?
C35 C34 H34 119.7 . . ?
C34 C35 H35 120.2 . . ?
C34 C35 C36 119.5(2) . . ?
C36 C35 H35 120.2 . . ?
C31 C36 C35 120.4(2) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O4 C18 C17 -90.66(17) . . . . ?
P1 O4 C18 C19 97.45(14) . . . . ?
P1 C25 C26 C27 177.13(16) . . . . ?
P1 C25 C30 C29 -176.55(16) . . . . ?
P1 C31 C32 C33 179.83(16) . . . . ?
P1 C31 C36 C35 -179.56(18) . . . . ?
O3 P1 O4 C18 64.56(13) . . . . ?
O3 P1 C25 C26 162.54(14) . . . . ?
O3 P1 C25 C30 -19.40(17) . . . . ?
O3 P1 C31 C32 -43.45(17) . . . . ?
O3 P1 C31 C36 137.11(17) . . . . ?
O4 P1 C25 C26 -72.91(15) . . . . ?
O4 P1 C25 C30 105.16(14) . . . . ?
O4 P1 C31 C32 -165.64(14) . . . . ?
O4 P1 C31 C36 14.92(18) . . . . ?
O4 C18 C19 C20 26.8(2) . . . . ?
O4 C18 C19 C24 -158.62(15) . . . . ?
N1 N2 C8 F1 177.58(13) . . . . ?
N1 N2 C8 F2 63.25(18) . . . . ?
N1 N2 C8 C7 -59.40(17) . . . . ?
N1 N2 C9 O2 -178.16(17) . . . . ?
N1 N2 C9 N3 3.76(17) . . . . ?
N1 C1 C2 C3 176.53(17) . . . . ?
N1 C1 C6 C5 -176.13(16) . . . . ?
N1 C1 C6 C7 6.5(2) . . . . ?
N2 N1 C1 C2 169.14(15) . . . . ?
N2 N1 C1 C6 -12.8(2) . . . . ?
N2 N1 C10 O1 -178.44(17) . . . . ?
N2 N1 C10 N3 0.06(18) . . . . ?
N3 C11 C12 C13 -177.84(16) . . . . ?
N3 C11 C16 C15 179.79(16) . . . . ?
C1 N1 N2 C8 39.5(2) . . . . ?
C1 N1 N2 C9 169.19(14) . . . . ?
C1 N1 C10 O1 11.0(3) . . . . ?
C1 N1 C10 N3 -170.54(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C6 C7 C8 -25.8(2) . . . . ?
C1 C6 C7 C17 94.55(19) . . . . ?
C2 C1 C6 C5 1.9(3) . . . . ?
C2 C1 C6 C7 -175.48(16) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 176.77(17) . . . . ?
C5 C6 C7 C8 156.83(16) . . . . ?
C5 C6 C7 C17 -82.82(19) . . . . ?
C6 C1 C2 C3 -1.5(3) . . . . ?
C6 C7 C8 F1 172.31(13) . . . . ?
C6 C7 C8 F2 -70.03(16) . . . . ?
C6 C7 C8 N2 51.79(17) . . . . ?
C6 C7 C17 C18 137.81(17) . . . . ?
C7 C17 C18 O4 0.8(3) . . . . ?
C7 C17 C18 C19 171.87(15) . . . . ?
C8 N2 C9 O2 -52.2(2) . . . . ?
C8 N2 C9 N3 129.72(14) . . . . ?
C8 C7 C17 C18 -101.45(19) . . . . ?
C9 N2 C8 F1 53.98(18) . . . . ?
C9 N2 C8 F2 -60.35(18) . . . . ?
C9 N2 C8 C7 177.00(13) . . . . ?
C9 N3 C10 O1 -179.01(17) . . . . ?
C9 N3 C10 N1 2.48(19) . . . . ?
C9 N3 C11 C12 43.3(2) . . . . ?
C9 N3 C11 C16 -135.83(17) . . . . ?
C10 N1 N2 C8 -132.11(15) . . . . ?
C10 N1 N2 C9 -2.42(18) . . . . ?
C10 N1 C1 C2 -21.1(3) . . . . ?
C10 N1 C1 C6 156.95(17) . . . . ?
C10 N3 C9 O2 178.06(19) . . . . ?
C10 N3 C9 N2 -3.95(19) . . . . ?
C10 N3 C11 C12 -133.94(18) . . . . ?
C10 N3 C11 C16 46.9(2) . . . . ?
C11 N3 C9 O2 0.5(3) . . . . ?
C11 N3 C9 N2 178.52(14) . . . . ?
C11 N3 C10 O1 -1.5(3) . . . . ?
C11 N3 C10 N1 179.99(15) . . . . ?
C11 C12 C13 C14 -2.1(3) . . . . ?
C12 C11 C16 C15 0.7(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C11 -1.9(3) . . . . ?
C16 C11 C12 C13 1.3(3) . . . . ?
C17 C7 C8 F1 50.49(17) . . . . ?
C17 C7 C8 F2 168.15(12) . . . . ?
C17 C7 C8 N2 -70.02(16) . . . . ?
C17 C18 C19 C20 -144.67(18) . . . . ?
C17 C18 C19 C24 29.9(3) . . . . ?
C18 C19 C20 C21 172.05(17) . . . . ?
C18 C19 C24 C23 -171.75(16) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C19 C24 C23 2.8(3) . . . . ?
C20 C21 C22 C23 1.3(3) . . . . ?
C21 C22 C23 C24 -1.1(3) . . . . ?
C22 C23 C24 C19 -1.0(3) . . . . ?
C24 C19 C20 C21 -2.6(3) . . . . ?
C25 P1 O4 C18 -59.48(12) . . . . ?
C25 P1 C31 C32 84.12(15) . . . . ?
C25 P1 C31 C36 -95.32(18) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C26 C25 C30 C29 1.5(3) . . . . ?
C26 C27 C28 C29 0.7(4) . . . . ?
C27 C28 C29 C30 -0.1(4) . . . . ?
C28 C29 C30 C25 -1.0(3) . . . . ?
C30 C25 C26 C27 -0.9(3) . . . . ?
C31 P1 O4 C18 -172.27(11) . . . . ?
C31 P1 C25 C26 33.72(17) . . . . ?
C31 P1 C25 C30 -148.22(14) . . . . ?
C31 C32 C33 C34 -0.7(3) . . . . ?
C32 C31 C36 C35 1.0(3) . . . . ?
C32 C33 C34 C35 1.8(4) . . . . ?
C33 C34 C35 C36 -1.5(4) . . . . ?
C34 C35 C36 C31 0.1(4) . . . . ?
C36 C31 C32 C33 -0.7(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 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.497
