# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2058334'
loop_
_audit_author_name
_audit_author_address
'Jaime Ponce de Leon'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2021-01-24 deposited with the CCDC.	2021-04-30 downloaded from the CCDC.
;
_audit_creation_date             2020-10-08
_audit_creation_method           
;
Olex2 1.3
(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 H14 F5 P'
_chemical_formula_sum            'C24 H14 F5 P'
_chemical_formula_weight         428.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H14 F5 P'
_chemical_oxdiff_usercomment     'colorless prism'
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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.4654(5)
_cell_length_b                   11.0784(6)
_cell_length_c                   18.2148(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1910.03(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2324
_cell_measurement_temperature    297.5(7)
_cell_measurement_theta_max      27.8970
_cell_measurement_theta_min      4.2300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 5 0.0659
1 0 -5 0.0659
0 -4 -5 0.1055
1 5 0 0.1368
-5 0 -2 0.0741
5 0 2 0.0611
0 -2 5 0.1227
0 2 -5 0.1349

_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.132
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 0.0000 5.0000 -0.1135 0.0467 -0.1686
1.0000 -0.0000 -5.0000 0.1135 -0.0467 0.1686
0.0000 -4.0000 -5.0000 0.2988 -0.1182 -0.0097
1.0000 5.0000 -0.0000 -0.2256 0.1052 0.2149
-5.0000 -0.0000 -2.0000 0.1754 0.3236 -0.1052
5.0000 0.0000 2.0000 -0.1754 -0.3236 0.1052
0.0000 -2.0000 5.0000 -0.0569 -0.0841 -0.2098
-0.0000 2.0000 -5.0000 0.0569 0.0841 0.2098

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7141
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.747
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.659
_diffrn_reflns_theta_min         3.608
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.5(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  58.00   1.00   13.09    --  -10.48  77.00-180.00   92
  2  ω     40.00  85.00   1.00   13.09    --   12.36-178.00  60.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0240716000
_diffrn_orient_matrix_UB_12      -0.0403131000
_diffrn_orient_matrix_UB_13      -0.0275142000
_diffrn_orient_matrix_UB_21      -0.0633812000
_diffrn_orient_matrix_UB_22      0.0337260000
_diffrn_orient_matrix_UB_23      -0.0033342000
_diffrn_orient_matrix_UB_31      0.0319763000
_diffrn_orient_matrix_UB_32      0.0365864000
_diffrn_orient_matrix_UB_33      -0.0273230000
_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         0.540
_reflns_Friedel_fraction_full    0.808
_reflns_Friedel_fraction_max     0.602
_reflns_number_gt                3029
_reflns_number_total             4039
_reflns_odcompleteness_completeness 99.56
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 891 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4039
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.058
_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)+(0.0346P)²+0.2106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0985
_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:
 C14(H14), C20(H20), C15(H15), C18(H18), C5(H5), C4(H4), C24(H24), C2(H2),
 C23(H23), C22(H22), C21(H21), C17(H17), C16(H16), C3(H3)
;
_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 0.40363(9) 0.65589(8) 0.71047(4) 0.0377(2) Uani 1 1 d . . . . .
F1 F 0.4680(2) 0.78431(17) 0.74873(11) 0.0546(6) Uani 1 1 d . . . . .
F5 F 0.1049(2) 0.5076(2) 0.70969(12) 0.0640(6) Uani 1 1 d . . . . .
F2 F 0.5156(3) 0.2838(2) 0.55265(13) 0.0739(8) Uani 1 1 d . . . . .
F4 F 0.0558(3) 0.2929(2) 0.64495(15) 0.0895(9) Uani 1 1 d . . . . .
F3 F 0.2606(3) 0.1832(2) 0.56637(15) 0.0915(9) Uani 1 1 d . . . . .
C7 C 0.4472(3) 0.4493(3) 0.62796(16) 0.0366(7) Uani 1 1 d . . . . .
C11 C 0.2106(4) 0.4547(3) 0.67178(18) 0.0442(8) Uani 1 1 d . . . . .
C6 C 0.5821(4) 0.5150(3) 0.63051(17) 0.0417(8) Uani 1 1 d . . . . .
C13 C 0.2773(4) 0.7479(3) 0.65944(18) 0.0407(8) Uani 1 1 d . . . . .
C1 C 0.5757(3) 0.6217(3) 0.67077(16) 0.0412(8) Uani 1 1 d . . . . .
C14 C 0.2550(4) 0.7257(3) 0.58564(19) 0.0472(9) Uani 1 1 d . . . . .
H14 H 0.301504 0.661548 0.563334 0.057 Uiso 1 1 calc R U . . .
C8 C 0.4179(4) 0.3414(3) 0.59325(18) 0.0486(9) Uani 1 1 d . . . . .
C19 C 0.3661(4) 0.6022(3) 0.80284(17) 0.0413(8) Uani 1 1 d . . . . .
C12 C 0.3406(3) 0.5081(3) 0.66732(17) 0.0376(8) Uani 1 1 d . . . . .
C20 C 0.2441(4) 0.6351(4) 0.84025(19) 0.0545(10) Uani 1 1 d . . . . .
H20 H 0.177081 0.683774 0.817536 0.065 Uiso 1 1 calc R U . . .
C15 C 0.1657(4) 0.7962(4) 0.5445(2) 0.0615(11) Uani 1 1 d . . . . .
H15 H 0.153338 0.780484 0.494781 0.074 Uiso 1 1 calc R U . . .
C10 C 0.1840(4) 0.3446(4) 0.6389(2) 0.0573(11) Uani 1 1 d . . . . .
C18 C 0.2079(4) 0.8452(3) 0.6912(2) 0.0537(9) Uani 1 1 d . . . . .
H18 H 0.222908 0.863193 0.740499 0.064 Uiso 1 1 calc R U . . .
C5 C 0.7099(4) 0.4786(4) 0.5997(2) 0.0572(11) Uani 1 1 d . . . . .
H5 H 0.715443 0.407097 0.573106 0.069 Uiso 1 1 calc R U . . .
C9 C 0.2873(5) 0.2891(4) 0.5996(2) 0.0586(11) Uani 1 1 d . . . . .
C4 C 0.8283(4) 0.5497(5) 0.6090(3) 0.0752(14) Uani 1 1 d . . . . .
H4 H 0.913419 0.525722 0.588093 0.090 Uiso 1 1 calc R U . . .
C24 C 0.4634(5) 0.5297(4) 0.8371(2) 0.0585(11) Uani 1 1 d . . . . .
H24 H 0.545394 0.506973 0.812609 0.070 Uiso 1 1 calc R U . . .
C2 C 0.6955(4) 0.6928(4) 0.6790(2) 0.0611(11) Uani 1 1 d . . . . .
H2 H 0.691076 0.765113 0.704787 0.073 Uiso 1 1 calc R U . . .
C23 C 0.4396(6) 0.4900(4) 0.9086(2) 0.0721(13) Uani 1 1 d . . . . .
H23 H 0.505557 0.440761 0.931720 0.087 Uiso 1 1 calc R U . . .
C22 C 0.3197(6) 0.5233(4) 0.9448(2) 0.0709(14) Uani 1 1 d . . . . .
H22 H 0.303873 0.496959 0.992555 0.085 Uiso 1 1 calc R U . . .
C21 C 0.2229(5) 0.5957(4) 0.9107(2) 0.0645(12) Uani 1 1 d . . . . .
H21 H 0.141381 0.618417 0.935604 0.077 Uiso 1 1 calc R U . . .
C17 C 0.1163(5) 0.9157(4) 0.6501(3) 0.0683(12) Uani 1 1 d . . . . .
H17 H 0.069349 0.980192 0.671827 0.082 Uiso 1 1 calc R U . . .
C16 C 0.0949(5) 0.8901(4) 0.5772(2) 0.0708(12) Uani 1 1 d . . . . .
H16 H 0.032250 0.936536 0.549803 0.085 Uiso 1 1 calc R U . . .
C3 C 0.8227(4) 0.6541(5) 0.6480(3) 0.0784(14) Uani 1 1 d . . . . .
H3 H 0.904083 0.700043 0.654053 0.094 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 F1 1.697(2) . ?
P1 C13 1.826(4) . ?
P1 C1 1.822(3) . ?
P1 C19 1.819(3) . ?
P1 C12 1.911(3) . ?
F5 C11 1.350(4) . ?
F2 C8 1.345(4) . ?
F4 C10 1.347(4) . ?
F3 C9 1.344(4) . ?
C7 C6 1.471(5) . ?
C7 C8 1.380(5) . ?
C7 C12 1.398(5) . ?
C11 C12 1.368(4) . ?
C11 C10 1.382(5) . ?
C6 C1 1.392(5) . ?
C6 C5 1.394(5) . ?
C13 C14 1.383(5) . ?
C13 C18 1.389(5) . ?
C1 C2 1.389(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(5) . ?
C8 C9 1.370(6) . ?
C19 C20 1.389(5) . ?
C19 C24 1.373(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.370(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(6) . ?
C10 C9 1.359(6) . ?
C18 H18 0.9300 . ?
C18 C17 1.387(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.379(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.358(7) . ?
C24 H24 0.9300 . ?
C24 C23 1.392(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(6) . ?
C23 H23 0.9300 . ?
C23 C22 1.363(6) . ?
C22 H22 0.9300 . ?
C22 C21 1.367(6) . ?
C21 H21 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.373(6) . ?
C16 H16 0.9300 . ?
C3 H3 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
F1 P1 C13 88.63(13) . . ?
F1 P1 C1 90.96(14) . . ?
F1 P1 C19 87.96(13) . . ?
F1 P1 C12 177.12(14) . . ?
C13 P1 C12 93.70(15) . . ?
C1 P1 C13 119.98(15) . . ?
C1 P1 C12 86.40(15) . . ?
C19 P1 C13 121.68(16) . . ?
C19 P1 C1 118.27(15) . . ?
C19 P1 C12 92.26(15) . . ?
C8 C7 C6 128.1(3) . . ?
C8 C7 C12 119.6(3) . . ?
C12 C7 C6 112.3(3) . . ?
F5 C11 C12 120.6(3) . . ?
F5 C11 C10 118.1(3) . . ?
C12 C11 C10 121.3(4) . . ?
C1 C6 C7 113.5(3) . . ?
C1 C6 C5 119.7(4) . . ?
C5 C6 C7 126.7(3) . . ?
C14 C13 P1 119.7(3) . . ?
C14 C13 C18 118.1(3) . . ?
C18 C13 P1 122.1(3) . . ?
C6 C1 P1 115.2(3) . . ?
C2 C1 P1 124.7(3) . . ?
C2 C1 C6 120.2(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.6(4) . . ?
C15 C14 H14 119.2 . . ?
F2 C8 C7 121.7(3) . . ?
F2 C8 C9 117.7(3) . . ?
C9 C8 C7 120.6(4) . . ?
C20 C19 P1 122.0(3) . . ?
C24 C19 P1 118.7(3) . . ?
C24 C19 C20 119.2(3) . . ?
C7 C12 P1 112.6(2) . . ?
C11 C12 P1 128.8(3) . . ?
C11 C12 C7 118.5(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.9(4) . . ?
C21 C20 H20 120.1 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.7(4) . . ?
C16 C15 H15 120.2 . . ?
F4 C10 C11 120.3(4) . . ?
F4 C10 C9 119.9(4) . . ?
C9 C10 C11 119.8(4) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.5(4) . . ?
C17 C18 H18 119.8 . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.4(4) . . ?
C4 C5 H5 120.3 . . ?
F3 C9 C8 120.1(4) . . ?
F3 C9 C10 119.8(4) . . ?
C10 C9 C8 120.1(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.3(4) . . ?
C3 C4 H4 119.4 . . ?
C19 C24 H24 120.0 . . ?
C19 C24 C23 120.1(4) . . ?
C23 C24 H24 120.0 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.1(4) . . ?
C3 C2 H2 120.5 . . ?
C24 C23 H23 119.9 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 119.9 . . ?
C23 C22 H22 120.1 . . ?
C23 C22 C21 119.8(4) . . ?
C21 C22 H22 120.1 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.9(4) . . ?
C22 C21 H21 119.5 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 119.9(4) . . ?
C16 C17 H17 120.0 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(4) . . ?
C17 C16 H16 119.9 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 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 C13 C14 C15 -177.0(3) . . . . ?
P1 C13 C18 C17 177.7(3) . . . . ?
P1 C1 C2 C3 177.6(3) . . . . ?
P1 C19 C20 C21 -177.8(3) . . . . ?
P1 C19 C24 C23 178.1(3) . . . . ?
F1 P1 C13 C14 135.1(3) . . . . ?
F1 P1 C13 C18 -41.0(3) . . . . ?
F1 P1 C1 C6 179.4(2) . . . . ?
F1 P1 C1 C2 0.1(3) . . . . ?
F1 P1 C19 C20 82.9(3) . . . . ?
F1 P1 C19 C24 -95.2(3) . . . . ?
F5 C11 C12 P1 1.2(5) . . . . ?
F5 C11 C12 C7 179.5(3) . . . . ?
F5 C11 C10 F4 0.0(5) . . . . ?
F5 C11 C10 C9 179.3(3) . . . . ?
F2 C8 C9 F3 0.6(5) . . . . ?
F2 C8 C9 C10 -178.8(3) . . . . ?
F4 C10 C9 F3 0.6(6) . . . . ?
F4 C10 C9 C8 180.0(3) . . . . ?
C7 C6 C1 P1 -0.2(3) . . . . ?
C7 C6 C1 C2 179.1(3) . . . . ?
C7 C6 C5 C4 -178.2(3) . . . . ?
C7 C8 C9 F3 -179.1(3) . . . . ?
C7 C8 C9 C10 1.5(6) . . . . ?
C11 C10 C9 F3 -178.7(3) . . . . ?
C11 C10 C9 C8 0.7(6) . . . . ?
C6 C7 C8 F2 -3.1(5) . . . . ?
C6 C7 C8 C9 176.5(3) . . . . ?
C6 C7 C12 P1 0.9(3) . . . . ?
C6 C7 C12 C11 -177.7(3) . . . . ?
C6 C1 C2 C3 -1.7(5) . . . . ?
C6 C5 C4 C3 0.4(6) . . . . ?
C13 P1 C1 C6 -91.6(3) . . . . ?
C13 P1 C1 C2 89.1(3) . . . . ?
C13 P1 C19 C20 -4.2(4) . . . . ?
C13 P1 C19 C24 177.6(3) . . . . ?
C13 C14 C15 C16 -1.0(6) . . . . ?
C13 C18 C17 C16 -0.7(6) . . . . ?
C1 P1 C13 C14 44.8(4) . . . . ?
C1 P1 C13 C18 -131.3(3) . . . . ?
C1 P1 C19 C20 172.9(3) . . . . ?
C1 P1 C19 C24 -5.3(3) . . . . ?
C1 C6 C5 C4 -0.6(5) . . . . ?
C1 C2 C3 C4 1.4(7) . . . . ?
C14 C13 C18 C17 1.6(5) . . . . ?
C14 C15 C16 C17 1.9(7) . . . . ?
C8 C7 C6 C1 -179.8(3) . . . . ?
C8 C7 C6 C5 -2.1(5) . . . . ?
C8 C7 C12 P1 -179.7(2) . . . . ?
C8 C7 C12 C11 1.7(5) . . . . ?
C19 P1 C13 C14 -138.2(3) . . . . ?
C19 P1 C13 C18 45.7(3) . . . . ?
C19 P1 C1 C6 91.2(3) . . . . ?
C19 P1 C1 C2 -88.1(3) . . . . ?
C19 C20 C21 C22 -0.5(6) . . . . ?
C19 C24 C23 C22 -0.1(7) . . . . ?
C12 P1 C13 C14 -43.2(3) . . . . ?
C12 P1 C13 C18 140.7(3) . . . . ?
C12 P1 C1 C6 0.6(2) . . . . ?
C12 P1 C1 C2 -178.7(3) . . . . ?
C12 P1 C19 C20 -99.9(3) . . . . ?
C12 P1 C19 C24 81.9(3) . . . . ?
C12 C7 C6 C1 -0.4(4) . . . . ?
C12 C7 C6 C5 177.2(3) . . . . ?
C12 C7 C8 F2 177.6(3) . . . . ?
C12 C7 C8 C9 -2.7(5) . . . . ?
C12 C11 C10 F4 179.0(3) . . . . ?
C12 C11 C10 C9 -1.7(6) . . . . ?
C20 C19 C24 C23 -0.1(6) . . . . ?
C10 C11 C12 P1 -177.8(3) . . . . ?
C10 C11 C12 C7 0.5(5) . . . . ?
C18 C13 C14 C15 -0.8(6) . . . . ?
C18 C17 C16 C15 -1.1(7) . . . . ?
C5 C6 C1 P1 -178.1(3) . . . . ?
C5 C6 C1 C2 1.3(5) . . . . ?
C5 C4 C3 C2 -0.8(7) . . . . ?
C24 C19 C20 C21 0.4(6) . . . . ?
C24 C23 C22 C21 0.1(7) . . . . ?
C23 C22 C21 C20 0.2(7) . . . . ?

_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 1.085
_oxdiff_exptl_absorpt_empirical_full_min 0.897
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2058336'
loop_
_audit_author_name
_audit_author_address
'Jaime Ponce de Leon'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2021-01-24 deposited with the CCDC.	2021-04-30 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.3
(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 H30 F P'
_chemical_formula_sum            'C24 H30 F P'
_chemical_formula_weight         368.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H30 F P'
_chemical_oxdiff_usercomment     'colorless prism'
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'
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/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                   9.4899(4)
_cell_length_b                   11.6773(4)
_cell_length_c                   18.4024(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.701(4)
_cell_angle_gamma                90
_cell_volume                     1989.39(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2333
_cell_measurement_temperature    294
_cell_measurement_theta_max      26.7780
_cell_measurement_theta_min      3.8890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -5 0.1482
1 0 5 0.2212
5 3 -5 0.1141
-5 -3 5 0.1141
0 5 1 0.1476
0 -5 -1 0.1296
4 1 -5 0.0691
-4 -1 5 0.0881

_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.157
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -0.0000 -5.0000 -0.2237 -0.0155 -0.0360
1.0000 0.0000 5.0000 0.2237 0.0155 0.0360
5.0000 3.0000 -5.0000 0.0844 -0.0001 -0.4225
-5.0000 -3.0000 5.0000 -0.0844 0.0001 0.4225
0.0000 5.0000 1.0000 0.0366 0.2822 -0.1133
-0.0000 -5.0000 -1.0000 -0.0366 -0.2822 0.1133
4.0000 1.0000 -5.0000 0.0324 -0.0849 -0.3188
-4.0000 -1.0000 5.0000 -0.0324 0.0849 0.3188

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8723
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.595
_diffrn_reflns_theta_min         3.489
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  33.00   1.00   11.47    --   12.36 -37.00  60.00   92
  2  ω     -1.00  74.00   1.00   11.47    --   12.36  19.00-120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0511466000
_diffrn_orient_matrix_UB_12      0.0004191000
_diffrn_orient_matrix_UB_13      0.0345152000
_diffrn_orient_matrix_UB_21      -0.0248430000
_diffrn_orient_matrix_UB_22      0.0548293000
_diffrn_orient_matrix_UB_23      0.0080694000
_diffrn_orient_matrix_UB_31      -0.0513276000
_diffrn_orient_matrix_UB_32      -0.0261606000
_diffrn_orient_matrix_UB_33      0.0174753000
_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                2982
_reflns_number_total             4641
_reflns_odcompleteness_completeness 98.67
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0561
_refine_ls_restrained_S_all      1.046
_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)+(0.0512P)²+0.7050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1469
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C14(H14A,H14B), C16(H16A,H16B), C24(H24A,H24B), C17(H17A,
 H17B), C15(H15A,H15B), C20(H20A,H20B), C23(H23A,H23B), C21(H21A,H21B),
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C2(H2), C8(H8), C10(H10), C4(H4), C9(H9), C3(H3)
;
_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 0.53070(6) 0.35853(5) 0.21974(3) 0.03669(18) Uani 1 1 d . . . . .
F1 F 0.35965(13) 0.35652(11) 0.23964(7) 0.0473(4) Uani 1 1 d . . . . .
C7 C 0.7185(2) 0.2553(2) 0.14462(12) 0.0416(5) Uani 1 1 d . . . . .
C13 C 0.6148(2) 0.35352(19) 0.32051(12) 0.0379(5) Uani 1 1 d . . . . .
H13 H 0.698785 0.404566 0.328313 0.046 Uiso 1 1 calc R U . . .
C1 C 0.4864(2) 0.22109(19) 0.17229(12) 0.0403(5) Uani 1 1 d . . . . .
C19 C 0.4795(2) 0.49533(19) 0.16991(12) 0.0399(5) Uani 1 1 d . . . . .
H19 H 0.568547 0.528425 0.160335 0.048 Uiso 1 1 calc R U . . .
C6 C 0.5909(3) 0.1809(2) 0.13572(12) 0.0433(6) Uani 1 1 d . . . . .
C12 C 0.7101(2) 0.35004(19) 0.18997(12) 0.0378(5) Uani 1 1 d . . . . .
C11 C 0.8269(3) 0.4246(2) 0.20629(13) 0.0496(6) Uani 1 1 d . . . . .
H11 H 0.823300 0.488035 0.236404 0.059 Uiso 1 1 calc R U . . .
C18 C 0.5239(3) 0.3916(2) 0.37506(12) 0.0492(6) Uani 1 1 d . . . . .
H18A H 0.495981 0.470987 0.365344 0.059 Uiso 1 1 calc R U . . .
H18B H 0.436472 0.345950 0.367047 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5705(3) 0.0766(2) 0.09854(14) 0.0582(7) Uani 1 1 d . . . . .
H5 H 0.637632 0.051339 0.072156 0.070 Uiso 1 1 calc R U . . .
C14 C 0.6732(3) 0.2330(2) 0.33980(13) 0.0506(6) Uani 1 1 d . . . . .
H14A H 0.593377 0.179208 0.330648 0.061 Uiso 1 1 calc R U . . .
H14B H 0.737398 0.212722 0.307482 0.061 Uiso 1 1 calc R U . . .
C2 C 0.3656(3) 0.1538(2) 0.17299(14) 0.0528(6) Uani 1 1 d . . . . .
H2 H 0.295109 0.179909 0.196994 0.063 Uiso 1 1 calc R U . . .
C8 C 0.8406(3) 0.2371(3) 0.11548(14) 0.0572(7) Uani 1 1 d . . . . .
H8 H 0.844955 0.174625 0.084721 0.069 Uiso 1 1 calc R U . . .
C16 C 0.6620(3) 0.2602(2) 0.47368(13) 0.0574(7) Uani 1 1 d . . . . .
H16A H 0.581666 0.207526 0.470103 0.069 Uiso 1 1 calc R U . . .
H16B H 0.718821 0.257774 0.524377 0.069 Uiso 1 1 calc R U . . .
C24 C 0.3811(3) 0.4714(2) 0.09406(13) 0.0548(7) Uani 1 1 d . . . . .
H24A H 0.429127 0.418792 0.066670 0.066 Uiso 1 1 calc R U . . .
H24B H 0.293284 0.434938 0.101148 0.066 Uiso 1 1 calc R U . . .
C17 C 0.6051(3) 0.3794(2) 0.45597(13) 0.0548(7) Uani 1 1 d . . . . .
H17A H 0.685065 0.432983 0.465801 0.066 Uiso 1 1 calc R U . . .
H17B H 0.540724 0.398805 0.488411 0.066 Uiso 1 1 calc R U . . .
C10 C 0.9486(3) 0.4053(3) 0.17808(16) 0.0627(8) Uani 1 1 d . . . . .
H10 H 1.026664 0.455210 0.189892 0.075 Uiso 1 1 calc R U . . .
C15 C 0.7546(3) 0.2229(3) 0.42067(14) 0.0639(8) Uani 1 1 d . . . . .
H15A H 0.784437 0.144034 0.431118 0.077 Uiso 1 1 calc R U . . .
H15B H 0.840772 0.269985 0.428510 0.077 Uiso 1 1 calc R U . . .
C4 C 0.4513(4) 0.0107(2) 0.10061(16) 0.0694(8) Uani 1 1 d . . . . .
H4 H 0.439353 -0.059720 0.076453 0.083 Uiso 1 1 calc R U . . .
C20 C 0.4132(3) 0.5857(2) 0.21154(14) 0.0569(7) Uani 1 1 d . . . . .
H20A H 0.480048 0.603504 0.258087 0.068 Uiso 1 1 calc R U . . .
H20B H 0.325468 0.555592 0.223231 0.068 Uiso 1 1 calc R U . . .
C9 C 0.9547(3) 0.3126(3) 0.13264(16) 0.0660(8) Uani 1 1 d . . . . .
H9 H 1.036304 0.300793 0.113422 0.079 Uiso 1 1 calc R U . . .
C3 C 0.3501(3) 0.0481(2) 0.13799(16) 0.0661(8) Uani 1 1 d . . . . .
H3 H 0.270750 0.002321 0.139883 0.079 Uiso 1 1 calc R U . . .
C23 C 0.3421(4) 0.5799(3) 0.04865(15) 0.0693(8) Uani 1 1 d . . . . .
H23A H 0.427935 0.610172 0.035008 0.083 Uiso 1 1 calc R U . . .
H23B H 0.272450 0.561693 0.003123 0.083 Uiso 1 1 calc R U . . .
C21 C 0.3780(3) 0.6945(2) 0.16572(15) 0.0630(8) Uani 1 1 d . . . . .
H21A H 0.331785 0.749014 0.192776 0.076 Uiso 1 1 calc R U . . .
H21B H 0.466797 0.728733 0.158115 0.076 Uiso 1 1 calc R U . . .
C22 C 0.2795(3) 0.6698(3) 0.09125(17) 0.0695(8) Uani 1 1 d . . . . .
H22A H 0.263724 0.739785 0.062159 0.083 Uiso 1 1 calc R U . . .
H22B H 0.186742 0.643810 0.098821 0.083 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 F1 1.7411(13) . ?
P1 C13 1.852(2) . ?
P1 C1 1.831(2) . ?
P1 C19 1.853(2) . ?
P1 C12 1.903(2) . ?
C7 C6 1.469(3) . ?
C7 C12 1.399(3) . ?
C7 C8 1.396(3) . ?
C13 H13 0.9800 . ?
C13 C18 1.527(3) . ?
C13 C14 1.525(3) . ?
C1 C6 1.396(3) . ?
C1 C2 1.393(3) . ?
C19 H19 0.9800 . ?
C19 C24 1.525(3) . ?
C19 C20 1.519(3) . ?
C6 C5 1.389(3) . ?
C12 C11 1.389(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.385(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.525(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.376(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.523(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.503(4) . ?
C16 C15 1.513(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C23 1.518(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C9 1.377(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C3 1.370(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.522(3) . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C22 1.508(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.507(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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
F1 P1 C13 90.32(8) . . ?
F1 P1 C1 87.80(9) . . ?
F1 P1 C19 87.73(8) . . ?
F1 P1 C12 174.14(9) . . ?
C13 P1 C19 122.09(10) . . ?
C13 P1 C12 94.05(10) . . ?
C1 P1 C13 116.94(10) . . ?
C1 P1 C19 120.79(10) . . ?
C1 P1 C12 86.74(10) . . ?
C19 P1 C12 93.24(10) . . ?
C12 C7 C6 112.37(19) . . ?
C8 C7 C6 126.9(2) . . ?
C8 C7 C12 120.6(2) . . ?
P1 C13 H13 106.6 . . ?
C18 C13 P1 117.89(16) . . ?
C18 C13 H13 106.6 . . ?
C14 C13 P1 108.47(15) . . ?
C14 C13 H13 106.6 . . ?
C14 C13 C18 110.14(19) . . ?
C6 C1 P1 114.30(17) . . ?
C2 C1 P1 126.38(19) . . ?
C2 C1 C6 119.2(2) . . ?
P1 C19 H19 106.6 . . ?
C24 C19 P1 109.67(16) . . ?
C24 C19 H19 106.6 . . ?
C20 C19 P1 116.23(15) . . ?
C20 C19 H19 106.6 . . ?
C20 C19 C24 110.5(2) . . ?
C1 C6 C7 113.7(2) . . ?
C5 C6 C7 126.5(2) . . ?
C5 C6 C1 119.7(2) . . ?
C7 C12 P1 112.63(16) . . ?
C11 C12 P1 128.82(18) . . ?
C11 C12 C7 118.5(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.7 . . ?
C13 C18 H18A 109.2 . . ?
C13 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C17 C18 C13 112.2(2) . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 C13 112.3(2) . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.3 . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C17 C16 C15 111.0(2) . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C19 C24 H24A 109.2 . . ?
C19 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C23 C24 C19 112.2(2) . . ?
C23 C24 H24A 109.2 . . ?
C23 C24 H24B 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C16 C17 C18 112.3(2) . . ?
C16 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 C14 111.5(2) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C19 C20 C21 111.4(2) . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C24 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C22 C23 C24 111.8(2) . . ?
C22 C23 H23A 109.3 . . ?
C22 C23 H23B 109.3 . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 C20 111.1(2) . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C23 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 C23 111.7(2) . . ?
C21 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?

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 C13 C18 C17 178.16(17) . . . . ?
P1 C13 C14 C15 175.74(18) . . . . ?
P1 C1 C6 C7 1.9(2) . . . . ?
P1 C1 C6 C5 179.12(18) . . . . ?
P1 C1 C2 C3 -176.2(2) . . . . ?
P1 C19 C24 C23 -176.77(19) . . . . ?
P1 C19 C20 C21 179.05(19) . . . . ?
P1 C12 C11 C10 -178.68(18) . . . . ?
F1 P1 C13 C18 -21.05(19) . . . . ?
F1 P1 C13 C14 104.93(16) . . . . ?
F1 P1 C1 C6 174.40(17) . . . . ?
F1 P1 C1 C2 -9.0(2) . . . . ?
F1 P1 C19 C24 -77.22(16) . . . . ?
F1 P1 C19 C20 49.00(19) . . . . ?
C7 C6 C5 C4 173.8(2) . . . . ?
C7 C12 C11 C10 0.1(3) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C13 P1 C1 C6 -96.36(18) . . . . ?
C13 P1 C1 C2 80.3(2) . . . . ?
C13 P1 C19 C24 -166.17(15) . . . . ?
C13 P1 C19 C20 -39.9(2) . . . . ?
C13 C18 C17 C16 -54.4(3) . . . . ?
C13 C14 C15 C16 55.6(3) . . . . ?
C1 P1 C13 C18 -108.75(19) . . . . ?
C1 P1 C13 C14 17.2(2) . . . . ?
C1 P1 C19 C24 8.9(2) . . . . ?
C1 P1 C19 C20 135.09(19) . . . . ?
C1 C6 C5 C4 -3.0(4) . . . . ?
C1 C2 C3 C4 -2.0(4) . . . . ?
C19 P1 C13 C18 66.5(2) . . . . ?
C19 P1 C13 C14 -167.55(15) . . . . ?
C19 P1 C1 C6 88.36(19) . . . . ?
C19 P1 C1 C2 -95.0(2) . . . . ?
C19 C24 C23 C22 -53.5(3) . . . . ?
C19 C20 C21 C22 56.4(3) . . . . ?
C6 C7 C12 P1 -4.3(2) . . . . ?
C6 C7 C12 C11 176.8(2) . . . . ?
C6 C7 C8 C9 -176.4(2) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C6 C5 C4 C3 1.3(4) . . . . ?
C12 P1 C13 C18 162.86(19) . . . . ?
C12 P1 C13 C14 -71.16(17) . . . . ?
C12 P1 C1 C6 -3.47(17) . . . . ?
C12 P1 C1 C2 173.2(2) . . . . ?
C12 P1 C19 C24 97.00(17) . . . . ?
C12 P1 C19 C20 -136.78(19) . . . . ?
C12 C7 C6 C1 1.6(3) . . . . ?
C12 C7 C6 C5 -175.3(2) . . . . ?
C12 C7 C8 C9 1.0(4) . . . . ?
C12 C11 C10 C9 0.8(4) . . . . ?
C11 C10 C9 C8 -0.8(4) . . . . ?
C18 C13 C14 C15 -53.9(3) . . . . ?
C5 C4 C3 C2 1.2(4) . . . . ?
C14 C13 C18 C17 53.0(3) . . . . ?
C2 C1 C6 C7 -175.0(2) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
C8 C7 C6 C1 179.2(2) . . . . ?
C8 C7 C6 C5 2.2(4) . . . . ?
C8 C7 C12 P1 177.95(17) . . . . ?
C8 C7 C12 C11 -1.0(3) . . . . ?
C24 C19 C20 C21 -55.2(3) . . . . ?
C24 C23 C22 C21 54.2(4) . . . . ?
C17 C16 C15 C14 -55.2(3) . . . . ?
C15 C16 C17 C18 54.8(3) . . . . ?
C20 C19 C24 C23 53.8(3) . . . . ?
C20 C21 C22 C23 -55.5(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 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.848
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2058335'
loop_
_audit_author_name
_audit_author_address
'Jaime Ponce de Leon'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2021-01-24 deposited with the CCDC.	2021-04-30 downloaded from the CCDC.
;
_audit_creation_date             2021-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 F9 P'
_chemical_formula_sum            'C24 H22 F9 P'
_chemical_formula_weight         512.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H22 F9 P'
_chemical_oxdiff_usercomment     'colorless plate'
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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.5949(5)
_cell_length_b                   17.1989(10)
_cell_length_c                   29.961(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4428.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2229
_cell_measurement_temperature    219.9(4)
_cell_measurement_theta_max      25.1980
_cell_measurement_theta_min      3.6010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2096
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.1375
0 0 -1 0.1095
5 3 -2 0.1466
-5 -3 2 0.1466
0 -1 0 0.0544
0 1 0 0.0114

_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.066
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -0.0000 1.0000 0.0218 -0.0092 -0.0005
-0.0000 0.0000 -1.0000 -0.0218 0.0092 0.0005
5.0000 3.0000 -2.0002 -0.0573 0.0101 -0.4293
-5.0000 -3.0000 2.0002 0.0573 -0.0101 0.4293
-0.0000 -1.0000 -0.0000 -0.0150 -0.0362 0.0130
0.0000 1.0000 0.0000 0.0150 0.0362 -0.0130

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12364
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.714
_diffrn_reflns_theta_min         3.344
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      219.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  74.00   1.00   94.15    --   12.36  37.00-180.00   77
  2  ω    -10.00  24.00   1.00   94.15    --   12.36 -19.00   0.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0116954000
_diffrn_orient_matrix_UB_12      0.0149531000
_diffrn_orient_matrix_UB_13      0.0218167000
_diffrn_orient_matrix_UB_21      -0.0233590000
_diffrn_orient_matrix_UB_22      0.0361737000
_diffrn_orient_matrix_UB_23      -0.0091870000
_diffrn_orient_matrix_UB_31      -0.0782610000
_diffrn_orient_matrix_UB_32      -0.0129998000
_diffrn_orient_matrix_UB_33      -0.0005107000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2489
_reflns_number_total             5253
_reflns_odcompleteness_completeness 98.83
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1505
_refine_ls_R_factor_gt           0.0710
_refine_ls_restrained_S_all      1.041
_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)+(0.0949P)²+1.5579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.2309
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H19(0.5) H19A(0.5) H24C(0.5) H24D(0.5) H24A(0.5) H24B(0.5)
 C21(0.5) H21A(0.5) H21B(0.5) C21A(0.5) H21C(0.5) H21D(0.5) C0AA(0.5) H0AA(0.5)
 H0AB(0.5) C1AA(0.5) H1AA(0.5) H1AB(0.5)
3.a Ternary CH refined with riding coordinates:
 C13(H13), C19(H19), C19(H19A)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C14(H14A,H14B), C15(H15A,
 H15B), C20(H20A,H20B), C22(H22A,H22B), C24(H24C,H24D), C24(H24A,H24B),
 C21(H21A,H21B), C21A(H21C,H21D), C0AA(H0AA,H0AB), C1AA(H1AA,H1AB)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.41669(10) 0.58933(5) 0.38362(3) 0.0541(3) Uani 1 1 d . . . . .
F1 F 0.3304(2) 0.53843(14) 0.42369(8) 0.0804(7) Uani 1 1 d . . . . .
F9 F 0.6600(3) 0.72901(13) 0.37794(10) 0.0865(8) Uani 1 1 d . . . . .
F8 F 0.7658(3) 0.80204(16) 0.30539(13) 0.1254(12) Uani 1 1 d . . . . .
F7 F 0.6621(4) 0.7611(2) 0.22413(12) 0.1416(15) Uani 1 1 d . . . . .
F5 F 0.2963(4) 0.5347(2) 0.21847(12) 0.1300(13) Uani 1 1 d . . . . .
F6 F 0.4653(4) 0.6457(2) 0.21366(10) 0.1246(12) Uani 1 1 d . . . . .
F2 F 0.1887(4) 0.43851(18) 0.38790(14) 0.1290(12) Uani 1 1 d . . . . .
F4 F 0.1008(4) 0.4195(2) 0.23618(15) 0.1618(19) Uani 1 1 d . . . . .
C12 C 0.5043(4) 0.64398(19) 0.33433(12) 0.0530(9) Uani 1 1 d . . . . .
C7 C 0.4528(4) 0.6214(2) 0.29245(13) 0.0598(10) Uani 1 1 d . . . . .
C11 C 0.6090(4) 0.7049(2) 0.33765(16) 0.0652(11) Uani 1 1 d . . . . .
C1 C 0.3161(4) 0.5310(2) 0.34058(15) 0.0622(10) Uani 1 1 d . . . . .
C13 C 0.6074(4) 0.5540(2) 0.40296(13) 0.0594(10) Uani 1 1 d . . . . .
H13 H 0.6857 0.5878 0.3892 0.071 Uiso 1 1 calc R . . . .
F3 F 0.0567(4) 0.36910(19) 0.32073(18) 0.1713(19) Uani 1 1 d . . . . .
C6 C 0.3445(4) 0.5552(2) 0.29610(15) 0.0651(11) Uani 1 1 d . . . . .
C10 C 0.6647(5) 0.7435(3) 0.3016(2) 0.0861(15) Uani 1 1 d . . . . .
C8 C 0.5106(5) 0.6633(3) 0.25527(15) 0.0818(14) Uani 1 1 d . . . . .
C9 C 0.6138(6) 0.7237(3) 0.2613(2) 0.0883(16) Uani 1 1 d . . . . .
C2 C 0.2195(5) 0.4682(3) 0.3475(2) 0.0874(14) Uani 1 1 d . . . . .
C5 C 0.2722(5) 0.5162(3) 0.26124(19) 0.0884(15) Uani 1 1 d . . . . .
C4 C 0.1744(6) 0.4554(4) 0.2699(3) 0.112(2) Uani 1 1 d . . . . .
C3 C 0.1489(6) 0.4297(3) 0.3119(3) 0.107(2) Uani 1 1 d . . . . .
C16 C 0.8288(7) 0.4502(3) 0.4464(2) 0.117(2) Uani 1 1 d . . . . .
H16A H 0.9354 0.4355 0.4529 0.140 Uiso 1 1 calc R . . . .
H16B H 0.7607 0.4133 0.4611 0.140 Uiso 1 1 calc R . . . .
C17 C 0.7988(6) 0.5295(4) 0.46432(18) 0.1029(17) Uani 1 1 d . . . . .
H17A H 0.8746 0.5654 0.4521 0.123 Uiso 1 1 calc R . . . .
H17B H 0.8109 0.5290 0.4965 0.123 Uiso 1 1 calc R . . . .
C18 C 0.6349(6) 0.5573(4) 0.45251(17) 0.1033(17) Uani 1 1 d . . . . .
H18A H 0.5590 0.5248 0.4676 0.124 Uiso 1 1 calc R . . . .
H18B H 0.6212 0.6103 0.4629 0.124 Uiso 1 1 calc R . . . .
C14 C 0.6373(6) 0.4735(3) 0.38546(19) 0.1078(19) Uani 1 1 d . . . . .
H14A H 0.6248 0.4731 0.3533 0.129 Uiso 1 1 calc R . . . .
H14B H 0.5620 0.4377 0.3981 0.129 Uiso 1 1 calc R . . . .
C15 C 0.8025(7) 0.4467(4) 0.3975(3) 0.146(3) Uani 1 1 d . . . . .
H15A H 0.8179 0.3938 0.3872 0.176 Uiso 1 1 calc R . . . .
H15B H 0.8778 0.4796 0.3825 0.176 Uiso 1 1 calc R . . . .
C19 C 0.3149(4) 0.6777(2) 0.40362(13) 0.0617(10) Uani 1 1 d . . . . .
H19 H 0.3757 0.7246 0.3973 0.074 Uiso 0.5 1 calc R . P A 1
H19A H 0.3686 0.7177 0.3861 0.074 Uiso 0.5 1 calc R . P B 2
C20 C 0.1579(6) 0.6833(3) 0.3847(2) 0.112(2) Uani 1 1 d . . . . .
H20A H 0.0960 0.6398 0.3951 0.135 Uiso 1 1 calc R . . . .
H20B H 0.1643 0.6803 0.3524 0.135 Uiso 1 1 calc R . . . .
C22 C 0.0778(7) 0.7597(4) 0.3980(2) 0.124(2) Uani 1 1 d . . . . .
H22A H 0.1320 0.8029 0.3842 0.148 Uiso 1 1 calc R . . . .
H22B H -0.0282 0.7595 0.3869 0.148 Uiso 1 1 calc R . . . .
C24 C 0.0752(8) 0.7710(4) 0.4470(2) 0.123(2) Uani 1 1 d . . . . .
H24C H 0.0323 0.7260 0.4621 0.148 Uiso 0.5 1 calc R . P C 2
H24D H 0.0151 0.8166 0.4551 0.148 Uiso 0.5 1 calc R . P C 2
H24A H 0.0602 0.8260 0.4529 0.148 Uiso 0.5 1 calc R . P D 1
H24B H -0.0147 0.7439 0.4589 0.148 Uiso 0.5 1 calc R . P D 1
C21 C 0.2724(15) 0.6720(9) 0.4552(5) 0.091(4) Uani 0.5 1 d . . P E 1
H21A H 0.1991 0.6299 0.4600 0.110 Uiso 0.5 1 calc R . P E 1
H21B H 0.3655 0.6610 0.4724 0.110 Uiso 0.5 1 calc R . P E 1
C21A C 0.3470(15) 0.7051(8) 0.4489(5) 0.089(4) Uani 0.5 1 d . . P E 2
H21C H 0.4581 0.7130 0.4523 0.106 Uiso 0.5 1 calc R . P E 2
H21D H 0.3149 0.6657 0.4701 0.106 Uiso 0.5 1 calc R . P E 2
C0AA C 0.260(2) 0.7826(9) 0.4593(5) 0.098(5) Uani 0.5 1 d . . P E 2
H0AA H 0.3037 0.8246 0.4417 0.118 Uiso 0.5 1 calc R . P E 2
H0AB H 0.2716 0.7957 0.4906 0.118 Uiso 0.5 1 calc R . P E 2
C1AA C 0.202(3) 0.7471(9) 0.4702(7) 0.116(6) Uani 0.5 1 d . . P E 1
H1AA H 0.1740 0.7422 0.5014 0.140 Uiso 0.5 1 calc R . P E 1
H1AB H 0.2814 0.7873 0.4682 0.140 Uiso 0.5 1 calc R . P E 1


_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 F1 1.661(2) . ?
P1 C12 1.906(4) . ?
P1 C1 1.849(4) . ?
P1 C13 1.842(3) . ?
P1 C19 1.853(4) . ?
F9 C11 1.350(5) . ?
F8 C10 1.335(6) . ?
F7 C9 1.352(5) . ?
F5 C5 1.336(6) . ?
F6 C8 1.341(5) . ?
F2 C2 1.339(6) . ?
F4 C4 1.342(6) . ?
C12 C7 1.386(5) . ?
C12 C11 1.385(5) . ?
C7 C6 1.476(6) . ?
C7 C8 1.416(6) . ?
C11 C10 1.355(6) . ?
C1 C6 1.417(6) . ?
C1 C2 1.377(6) . ?
C13 H13 0.9800 . ?
C13 C18 1.504(6) . ?
C13 C14 1.503(6) . ?
F3 C3 1.335(7) . ?
C6 C5 1.388(6) . ?
C10 C9 1.329(7) . ?
C8 C9 1.378(7) . ?
C2 C3 1.395(8) . ?
C5 C4 1.366(9) . ?
C4 C3 1.353(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.488(7) . ?
C16 C15 1.483(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.529(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.536(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C19 H19 0.9800 . ?
C19 H19A 0.9800 . ?
C19 C20 1.467(6) . ?
C19 C21 1.591(14) . ?
C19 C21A 1.462(15) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C22 1.536(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C24 1.482(8) . ?
C24 H24C 0.9700 . ?
C24 H24D 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C0AA 1.64(2) . ?
C24 C1AA 1.36(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C1AA 1.50(2) . ?
C21A H21C 0.9700 . ?
C21A H21D 0.9700 . ?
C21A C0AA 1.56(2) . ?
C0AA H0AA 0.9700 . ?
C0AA H0AB 0.9700 . ?
C1AA H1AA 0.9700 . ?
C1AA H1AB 0.9700 . ?

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
F1 P1 C12 175.37(15) . . ?
F1 P1 C1 90.53(17) . . ?
F1 P1 C13 89.78(14) . . ?
F1 P1 C19 89.30(16) . . ?
C1 P1 C12 84.95(18) . . ?
C1 P1 C19 116.75(16) . . ?
C13 P1 C12 93.14(16) . . ?
C13 P1 C1 117.15(17) . . ?
C13 P1 C19 126.09(18) . . ?
C19 P1 C12 91.86(16) . . ?
C7 C12 P1 115.9(3) . . ?
C11 C12 P1 125.1(3) . . ?
C11 C12 C7 119.0(4) . . ?
C12 C7 C6 110.5(3) . . ?
C12 C7 C8 117.3(4) . . ?
C8 C7 C6 132.2(4) . . ?
F9 C11 C12 120.5(4) . . ?
F9 C11 C10 116.6(4) . . ?
C10 C11 C12 122.9(5) . . ?
C6 C1 P1 114.6(3) . . ?
C2 C1 P1 127.0(4) . . ?
C2 C1 C6 118.4(4) . . ?
P1 C13 H13 106.5 . . ?
C18 C13 P1 116.0(3) . . ?
C18 C13 H13 106.5 . . ?
C14 C13 P1 110.2(3) . . ?
C14 C13 H13 106.5 . . ?
C14 C13 C18 110.6(4) . . ?
C1 C6 C7 113.9(3) . . ?
C5 C6 C7 126.8(5) . . ?
C5 C6 C1 119.3(4) . . ?
F8 C10 C11 122.1(6) . . ?
C9 C10 F8 119.0(5) . . ?
C9 C10 C11 118.9(5) . . ?
F6 C8 C7 121.0(5) . . ?
F6 C8 C9 118.6(5) . . ?
C9 C8 C7 120.4(5) . . ?
F7 C9 C8 116.7(6) . . ?
C10 C9 F7 121.7(6) . . ?
C10 C9 C8 121.6(4) . . ?
F2 C2 C1 123.7(5) . . ?
F2 C2 C3 115.0(5) . . ?
C1 C2 C3 121.2(6) . . ?
F5 C5 C6 122.5(5) . . ?
F5 C5 C4 117.3(5) . . ?
C4 C5 C6 120.1(6) . . ?
F4 C4 C5 120.0(8) . . ?
F4 C4 C3 118.2(7) . . ?
C3 C4 C5 121.8(5) . . ?
F3 C3 C2 118.6(7) . . ?
F3 C3 C4 122.4(7) . . ?
C4 C3 C2 119.1(5) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C15 C16 C17 111.5(5) . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C16 C17 C18 111.3(4) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C13 C18 C17 111.2(4) . . ?
C13 C18 H18A 109.4 . . ?
C13 C18 H18B 109.4 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 C15 110.6(4) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C16 C15 C14 111.2(5) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
P1 C19 H19 111.2 . . ?
P1 C19 H19A 100.4 . . ?
C20 C19 P1 111.3(3) . . ?
C20 C19 H19 111.2 . . ?
C20 C19 H19A 100.4 . . ?
C20 C19 C21 99.7(6) . . ?
C21 C19 P1 111.8(5) . . ?
C21 C19 H19 111.2 . . ?
C21A C19 P1 118.4(5) . . ?
C21A C19 H19A 100.4 . . ?
C21A C19 C20 120.7(6) . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C19 C20 C22 111.6(4) . . ?
H20A C20 H20B 108.0 . . ?
C22 C20 H20A 109.3 . . ?
C22 C20 H20B 109.3 . . ?
C20 C22 H22A 109.2 . . ?
C20 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C24 C22 C20 112.2(5) . . ?
C24 C22 H22A 109.2 . . ?
C24 C22 H22B 109.2 . . ?
C22 C24 H24C 111.2 . . ?
C22 C24 H24D 111.2 . . ?
C22 C24 H24A 108.0 . . ?
C22 C24 H24B 108.0 . . ?
C22 C24 C0AA 102.9(7) . . ?
H24C C24 H24D 109.1 . . ?
H24A C24 H24B 107.3 . . ?
C0AA C24 H24C 111.2 . . ?
C0AA C24 H24D 111.2 . . ?
C1AA C24 C22 117.0(9) . . ?
C1AA C24 H24A 108.0 . . ?
C1AA C24 H24B 108.0 . . ?
C19 C21 H21A 109.8 . . ?
C19 C21 H21B 109.8 . . ?
H21A C21 H21B 108.3 . . ?
C1AA C21 C19 109.3(11) . . ?
C1AA C21 H21A 109.8 . . ?
C1AA C21 H21B 109.8 . . ?
C19 C21A H21C 109.3 . . ?
C19 C21A H21D 109.3 . . ?
C19 C21A C0AA 111.7(11) . . ?
H21C C21A H21D 107.9 . . ?
C0AA C21A H21C 109.3 . . ?
C0AA C21A H21D 109.3 . . ?
C24 C0AA H0AA 110.0 . . ?
C24 C0AA H0AB 110.0 . . ?
C21A C0AA C24 108.3(11) . . ?
C21A C0AA H0AA 110.0 . . ?
C21A C0AA H0AB 110.0 . . ?
H0AA C0AA H0AB 108.4 . . ?
C24 C1AA C21 115.6(16) . . ?
C24 C1AA H1AA 108.4 . . ?
C24 C1AA H1AB 108.4 . . ?
C21 C1AA H1AA 108.4 . . ?
C21 C1AA H1AB 108.4 . . ?
H1AA C1AA H1AB 107.4 . . ?

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 C12 C7 C6 -3.1(3) . . . . ?
P1 C12 C7 C8 177.3(2) . . . . ?
P1 C12 C11 F9 1.6(5) . . . . ?
P1 C12 C11 C10 -178.0(3) . . . . ?
P1 C1 C6 C7 1.6(4) . . . . ?
P1 C1 C6 C5 -178.8(3) . . . . ?
P1 C1 C2 F2 -2.4(6) . . . . ?
P1 C1 C2 C3 179.1(3) . . . . ?
P1 C13 C18 C17 -177.8(4) . . . . ?
P1 C13 C14 C15 174.4(5) . . . . ?
P1 C19 C20 C22 -175.4(4) . . . . ?
P1 C19 C21 C1AA 175.5(11) . . . . ?
P1 C19 C21A C0AA 176.4(9) . . . . ?
F1 P1 C1 C6 176.4(2) . . . . ?
F1 P1 C1 C2 -3.6(3) . . . . ?
F1 P1 C13 C18 -46.2(4) . . . . ?
F1 P1 C13 C14 80.4(4) . . . . ?
F1 P1 C19 C20 -84.3(4) . . . . ?
F1 P1 C19 C21 26.2(6) . . . . ?
F1 P1 C19 C21A 62.2(7) . . . . ?
F9 C11 C10 F8 0.5(6) . . . . ?
F9 C11 C10 C9 -177.7(4) . . . . ?
F8 C10 C9 F7 0.2(7) . . . . ?
F8 C10 C9 C8 179.4(3) . . . . ?
F5 C5 C4 F4 -3.4(6) . . . . ?
F5 C5 C4 C3 176.5(4) . . . . ?
F6 C8 C9 F7 0.0(6) . . . . ?
F6 C8 C9 C10 -179.2(4) . . . . ?
F2 C2 C3 F3 1.2(6) . . . . ?
F2 C2 C3 C4 -179.6(5) . . . . ?
F4 C4 C3 F3 1.7(8) . . . . ?
F4 C4 C3 C2 -177.5(4) . . . . ?
C12 P1 C1 C6 -2.6(3) . . . . ?
C12 P1 C1 C2 177.4(3) . . . . ?
C12 P1 C13 C18 137.4(4) . . . . ?
C12 P1 C13 C14 -96.0(4) . . . . ?
C12 P1 C19 C20 91.2(4) . . . . ?
C12 P1 C19 C21 -158.3(6) . . . . ?
C12 P1 C19 C21A -122.3(7) . . . . ?
C12 C7 C6 C1 1.0(4) . . . . ?
C12 C7 C6 C5 -178.6(3) . . . . ?
C12 C7 C8 F6 -179.3(3) . . . . ?
C12 C7 C8 C9 0.0(5) . . . . ?
C12 C11 C10 F8 -179.9(3) . . . . ?
C12 C11 C10 C9 1.9(6) . . . . ?
C7 C12 C11 F9 179.1(3) . . . . ?
C7 C12 C11 C10 -0.5(5) . . . . ?
C7 C6 C5 F5 1.2(6) . . . . ?
C7 C6 C5 C4 179.9(3) . . . . ?
C7 C8 C9 F7 -179.3(3) . . . . ?
C7 C8 C9 C10 1.5(6) . . . . ?
C11 C12 C7 C6 179.1(3) . . . . ?
C11 C12 C7 C8 -0.5(5) . . . . ?
C11 C10 C9 F7 178.4(3) . . . . ?
C11 C10 C9 C8 -2.4(7) . . . . ?
C1 P1 C13 C18 -136.7(4) . . . . ?
C1 P1 C13 C14 -10.0(4) . . . . ?
C1 P1 C19 C20 5.9(4) . . . . ?
C1 P1 C19 C21 116.4(6) . . . . ?
C1 P1 C19 C21A 152.4(7) . . . . ?
C1 C6 C5 F5 -178.4(3) . . . . ?
C1 C6 C5 C4 0.2(5) . . . . ?
C1 C2 C3 F3 179.8(4) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
C13 P1 C1 C6 -93.5(3) . . . . ?
C13 P1 C1 C2 86.4(4) . . . . ?
C13 P1 C19 C20 -173.5(4) . . . . ?
C13 P1 C19 C21 -63.0(6) . . . . ?
C13 P1 C19 C21A -27.1(8) . . . . ?
C13 C14 C15 C16 56.4(8) . . . . ?
C6 C7 C8 F6 1.3(6) . . . . ?
C6 C7 C8 C9 -179.5(4) . . . . ?
C6 C1 C2 F2 177.6(4) . . . . ?
C6 C1 C2 C3 -0.9(6) . . . . ?
C6 C5 C4 F4 177.9(3) . . . . ?
C6 C5 C4 C3 -2.2(7) . . . . ?
C8 C7 C6 C1 -179.5(3) . . . . ?
C8 C7 C6 C5 0.8(6) . . . . ?
C2 C1 C6 C7 -178.4(3) . . . . ?
C2 C1 C6 C5 1.3(5) . . . . ?
C5 C4 C3 F3 -178.3(4) . . . . ?
C5 C4 C3 C2 2.5(8) . . . . ?
C16 C17 C18 C13 -55.3(7) . . . . ?
C17 C16 C15 C14 -56.2(8) . . . . ?
C18 C13 C14 C15 -56.0(7) . . . . ?
C14 C13 C18 C17 55.7(6) . . . . ?
C15 C16 C17 C18 55.6(7) . . . . ?
C19 P1 C1 C6 86.9(3) . . . . ?
C19 P1 C1 C2 -93.1(4) . . . . ?
C19 P1 C13 C18 42.7(4) . . . . ?
C19 P1 C13 C14 169.4(3) . . . . ?
C19 C20 C22 C24 -54.5(8) . . . . ?
C19 C21 C1AA C24 56.3(17) . . . . ?
C19 C21A C0AA C24 51.8(14) . . . . ?
C20 C19 C21 C1AA -66.8(13) . . . . ?
C20 C19 C21A C0AA -40.3(14) . . . . ?
C20 C22 C24 C0AA 66.8(8) . . . . ?
C20 C22 C24 C1AA 37.1(12) . . . . ?
C22 C24 C0AA C21A -65.2(12) . . . . ?
C22 C24 C1AA C21 -40.2(17) . . . . ?
C21 C19 C20 C22 66.6(8) . . . . ?
C21A C19 C20 C22 39.1(10) . . . . ?

_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 1.266
_oxdiff_exptl_absorpt_empirical_full_min 0.776
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_preparation       Luminescent
