# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_xieshaol_0622
_database_code_depnum_ccdc_archive 'CCDC 2034797'
loop_
_audit_author_name
_audit_author_address
'Xie Shaolei' 'Lanzhou University'
_audit_update_record             
;
2020-09-30 deposited with the CCDC.	2020-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-09-30
_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         'C27 H22 F O2 P'
_chemical_formula_sum            'C27 H22 F O2 P'
_chemical_formula_weight         428.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.1721(4)
_cell_length_b                   9.7020(3)
_cell_length_c                   14.1513(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.467(4)
_cell_angle_gamma                90
_cell_volume                     1316.74(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1673
_cell_measurement_temperature    294.82(10)
_cell_measurement_theta_max      66.0090
_cell_measurement_theta_min      9.2110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82855
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.081
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8594
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.578
_diffrn_reflns_theta_max         66.578
_diffrn_reflns_theta_min         4.611
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.82(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_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    -24.00  11.00   1.00    1.00    --    0.00 106.00  69.00   35
  2  ω      4.00  67.00   1.00    1.00    --    0.00  77.00 -90.00   63
  3  ω     -8.00  95.00   1.00    2.00    --   54.00 -19.00 -90.00  103
  4  ω     85.00 178.00   1.00    4.00    --  108.00  38.00-180.00   93
  5  ω     88.00 127.00   1.00    4.00    --  108.00 -50.00 -30.00   39
  6  ω     89.00 116.00   1.00    4.00    --  108.00-111.00  90.00   27
  7  ω     62.00 136.00   1.00    4.00    --  108.00 -77.00   0.00   74
  8  ω     52.00 107.00   1.00    4.00    --  108.00-113.00-118.00   55
  9  ω     87.00 132.00   1.00    4.00    --  108.00 -77.00-180.00   45
 10  ω     65.00  91.00   1.00    2.00    --   54.00-125.00-180.00   26
 11  ω     36.00 124.00   1.00    4.00    --  108.00 -38.00-180.00   88
 12  ω     78.00 120.00   1.00    2.00    --   54.00  57.00-120.00   42
 13  ω    104.00 129.00   1.00    4.00    --  108.00 111.00  30.00   25
 14  ω    112.00 147.00   1.00    4.00    --  108.00 111.00 120.00   35
 15  ω    116.00 167.00   1.00    4.00    --  108.00  38.00 120.00   51
 16  ω    112.00 146.00   1.00    4.00    --  108.00 178.00 -90.00   34
 17  ω     70.00  96.00   1.00    4.00    --  108.00 178.00 -90.00   26
 18  ω     35.00 124.00   1.00    4.00    --  108.00 -25.00   0.00   89
 19  ω     49.00 130.00   1.00    4.00    --  108.00 -50.00  90.00   81
 20  ω     43.00  84.00   1.00    4.00    --  108.00 -50.00 -30.00   41
 21  ω     37.00 103.00   1.00    2.00    --   54.00-125.00  30.00   66
 22  ω     36.00 104.00   1.00    4.00    --  108.00-111.00   0.00   68
 23  ω     -1.00  84.00   1.00    2.00    --   54.00 -77.00  60.00   85
 24  ω    -11.00  80.00   1.00    2.00    --   54.00 -38.00  90.00   91
 25  ω    -15.00  11.00   1.00    2.00    --   54.00 -57.00  90.00   26
 26  ω    -33.00  19.00   1.00    1.00    --    0.00 -57.00 -30.00   52
 27  ω      1.00  73.00   1.00    2.00    --   54.00 -57.00-150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0286739000
_diffrn_orient_matrix_UB_12      0.1441526000
_diffrn_orient_matrix_UB_13      -0.0344956000
_diffrn_orient_matrix_UB_21      0.0369221000
_diffrn_orient_matrix_UB_22      0.0534070000
_diffrn_orient_matrix_UB_23      0.1082558000
_diffrn_orient_matrix_UB_31      0.1536435000
_diffrn_orient_matrix_UB_32      -0.0397839000
_diffrn_orient_matrix_UB_33      0.0206115000
_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         0.879
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3642
_reflns_number_total             4657
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1315 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4657
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.81921(10) -0.17767(11) -0.18557(7) 0.0514(2) Uani 1 1 d . . . . .
F1 F -1.0719(2) -0.1463(2) -0.17884(16) 0.0544(6) Uani 1 1 d . . . . .
O1 O -0.7393(3) -0.2035(4) -0.2542(2) 0.0703(9) Uani 1 1 d . . . . .
O2 O -0.9679(3) -0.4349(3) -0.2771(3) 0.0728(9) Uani 1 1 d . . . . .
C1 C -1.0500(4) -0.3582(4) -0.2593(3) 0.0508(9) Uani 1 1 d . . . . .
C2 C -1.1844(4) -0.4074(4) -0.2523(3) 0.0533(10) Uani 1 1 d . . . . .
C3 C -1.3005(4) -0.3233(5) -0.2640(3) 0.0586(10) Uani 1 1 d . . . . .
H3 H -1.295978 -0.229710 -0.276905 0.070 Uiso 1 1 calc R U . . .
C4 C -1.4215(4) -0.3781(6) -0.2565(4) 0.0698(13) Uani 1 1 d . . . . .
H4 H -1.498223 -0.321207 -0.265446 0.084 Uiso 1 1 calc R U . . .
C5 C -1.4309(5) -0.5160(6) -0.2361(4) 0.0738(14) Uani 1 1 d . . . . .
C6 C -1.1958(5) -0.5468(5) -0.2336(3) 0.0668(12) Uani 1 1 d . . . . .
H6 H -1.120608 -0.605022 -0.226761 0.080 Uiso 1 1 calc R U . . .
C7 C -1.3163(5) -0.5996(6) -0.2251(4) 0.0776(15) Uani 1 1 d . . . . .
H7 H -1.321313 -0.692915 -0.211782 0.093 Uiso 1 1 calc R U . . .
C8 C -1.5618(6) -0.5758(7) -0.2239(5) 0.106(2) Uani 1 1 d . . . . .
H8A H -1.541462 -0.608472 -0.156547 0.159 Uiso 1 1 calc R U . . .
H8B H -1.594506 -0.650958 -0.269909 0.159 Uiso 1 1 calc R U . . .
H8C H -1.632418 -0.505808 -0.237650 0.159 Uiso 1 1 calc R U . . .
C9 C -1.0124(4) -0.2037(4) -0.2461(3) 0.0477(9) Uani 1 1 d . . . . .
C10 C -1.0651(4) -0.1288(4) -0.3452(3) 0.0568(11) Uani 1 1 d . . . . .
C11 C -1.0254(5) -0.1722(7) -0.4249(3) 0.0813(14) Uani 1 1 d . . . . .
H11 H -0.969384 -0.249640 -0.419071 0.098 Uiso 1 1 calc R U . . .
C12 C -1.0718(7) -0.0965(8) -0.5153(4) 0.107(2) Uani 1 1 d . . . . .
H12 H -1.043269 -0.122459 -0.568701 0.129 Uiso 1 1 calc R U . . .
C13 C -1.1578(7) 0.0141(9) -0.5249(5) 0.116(3) Uani 1 1 d . . . . .
H13 H -1.189692 0.061543 -0.585432 0.139 Uiso 1 1 calc R U . . .
C14 C -1.1971(7) 0.0553(8) -0.4469(6) 0.111(2) Uani 1 1 d . . . . .
H14 H -1.254644 0.131777 -0.453671 0.133 Uiso 1 1 calc R U . . .
C15 C -1.1519(5) -0.0163(5) -0.3567(4) 0.0792(15) Uani 1 1 d . . . . .
H15 H -1.180407 0.011836 -0.303796 0.095 Uiso 1 1 calc R U . . .
C16 C -0.8142(4) -0.0018(4) -0.1462(3) 0.0505(9) Uani 1 1 d . . . . .
C17 C -0.8000(4) 0.0384(5) -0.0499(3) 0.0661(11) Uani 1 1 d . . . . .
H17 H -0.790700 -0.028148 -0.000771 0.079 Uiso 1 1 calc R U . . .
C18 C -0.7993(5) 0.1778(6) -0.0252(4) 0.0761(14) Uani 1 1 d . . . . .
H18 H -0.787487 0.204125 0.040281 0.091 Uiso 1 1 calc R U . . .
C19 C -0.8163(5) 0.2758(5) -0.0983(4) 0.0764(14) Uani 1 1 d . . . . .
H19 H -0.818071 0.368599 -0.082316 0.092 Uiso 1 1 calc R U . . .
C20 C -0.8306(5) 0.2384(5) -0.1944(4) 0.0708(13) Uani 1 1 d . . . . .
H20 H -0.841546 0.305365 -0.243460 0.085 Uiso 1 1 calc R U . . .
C21 C -0.8286(4) 0.0996(5) -0.2181(3) 0.0635(11) Uani 1 1 d . . . . .
H21 H -0.837027 0.074190 -0.283234 0.076 Uiso 1 1 calc R U . . .
C22 C -0.7667(4) -0.2842(5) -0.0746(3) 0.0565(10) Uani 1 1 d . . . . .
C23 C -0.6289(5) -0.3261(6) -0.0400(4) 0.0766(14) Uani 1 1 d . . . . .
H23 H -0.568008 -0.300078 -0.073362 0.092 Uiso 1 1 calc R U . . .
C24 C -0.5830(6) -0.4081(7) 0.0458(4) 0.0956(19) Uani 1 1 d . . . . .
H24 H -0.490157 -0.435486 0.069927 0.115 Uiso 1 1 calc R U . . .
C25 C -0.6699(7) -0.4488(6) 0.0948(4) 0.0920(18) Uani 1 1 d . . . . .
H25 H -0.637131 -0.505447 0.150730 0.110 Uiso 1 1 calc R U . . .
C26 C -0.8065(6) -0.4066(6) 0.0621(4) 0.0829(16) Uani 1 1 d . . . . .
H26 H -0.866502 -0.433321 0.095997 0.100 Uiso 1 1 calc R U . . .
C27 C -0.8538(5) -0.3231(5) -0.0226(3) 0.0683(12) Uani 1 1 d . . . . .
H27 H -0.945895 -0.292982 -0.044500 0.082 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 1.481(3) . ?
P1 C9 1.880(4) . ?
P1 C16 1.791(4) . ?
P1 C22 1.806(4) . ?
F1 C9 1.402(4) . ?
O2 C1 1.207(5) . ?
C1 C2 1.483(5) . ?
C1 C9 1.543(6) . ?
C2 C3 1.399(6) . ?
C2 C6 1.390(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(7) . ?
C5 C7 1.385(7) . ?
C5 C8 1.514(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.370(6) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.510(5) . ?
C10 C11 1.385(6) . ?
C10 C15 1.379(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.412(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.354(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(6) . ?
C16 C21 1.387(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.367(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.390(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(6) . ?
C22 C27 1.380(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.396(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.351(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.372(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.393(6) . ?
C27 H27 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 C9 113.43(17) . . ?
O1 P1 C16 113.6(2) . . ?
O1 P1 C22 113.9(2) . . ?
C16 P1 C9 100.74(18) . . ?
C16 P1 C22 107.76(19) . . ?
C22 P1 C9 106.29(18) . . ?
O2 C1 C2 122.3(4) . . ?
O2 C1 C9 117.6(4) . . ?
C2 C1 C9 120.1(4) . . ?
C3 C2 C1 124.4(4) . . ?
C6 C2 C1 117.6(4) . . ?
C6 C2 C3 118.0(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(5) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C7 118.5(4) . . ?
C4 C5 C8 121.4(5) . . ?
C7 C5 C8 120.1(5) . . ?
C2 C6 H6 119.5 . . ?
C7 C6 C2 120.9(5) . . ?
C7 C6 H6 119.5 . . ?
C5 C7 H7 119.5 . . ?
C6 C7 C5 121.0(5) . . ?
C6 C7 H7 119.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F1 C9 P1 105.1(2) . . ?
F1 C9 C1 108.8(3) . . ?
F1 C9 C10 109.8(3) . . ?
C1 C9 P1 111.4(3) . . ?
C10 C9 P1 110.6(3) . . ?
C10 C9 C1 111.0(3) . . ?
C11 C10 C9 120.0(4) . . ?
C15 C10 C9 120.4(4) . . ?
C15 C10 C11 119.5(5) . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.7(6) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(7) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(6) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(7) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.5(6) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 P1 124.0(3) . . ?
C17 C16 C21 118.4(4) . . ?
C21 C16 P1 117.5(3) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.7(5) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(5) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.7(5) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.5(4) . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 121.1(4) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 P1 116.5(4) . . ?
C27 C22 P1 124.3(3) . . ?
C27 C22 C23 119.1(4) . . ?
C22 C23 H23 120.6 . . ?
C22 C23 C24 118.7(5) . . ?
C24 C23 H23 120.6 . . ?
C23 C24 H24 119.1 . . ?
C25 C24 C23 121.8(5) . . ?
C25 C24 H24 119.1 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.1(5) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.5 . . ?
C25 C26 C27 119.0(6) . . ?
C27 C26 H26 120.5 . . ?
C22 C27 C26 121.3(5) . . ?
C22 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?

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 C9 C10 C11 67.6(4) . . . . ?
P1 C9 C10 C15 -111.9(4) . . . . ?
P1 C16 C17 C18 -178.9(3) . . . . ?
P1 C16 C21 C20 177.8(3) . . . . ?
P1 C22 C23 C24 179.7(4) . . . . ?
P1 C22 C27 C26 179.4(4) . . . . ?
F1 C9 C10 C11 -176.9(4) . . . . ?
F1 C9 C10 C15 3.7(5) . . . . ?
O1 P1 C9 F1 -167.3(2) . . . . ?
O1 P1 C9 C1 75.0(3) . . . . ?
O1 P1 C9 C10 -48.9(3) . . . . ?
O1 P1 C16 C17 -138.9(3) . . . . ?
O1 P1 C16 C21 42.5(4) . . . . ?
O1 P1 C22 C23 29.4(4) . . . . ?
O1 P1 C22 C27 -151.8(4) . . . . ?
O2 C1 C2 C3 -158.5(4) . . . . ?
O2 C1 C2 C6 20.9(6) . . . . ?
O2 C1 C9 P1 -34.2(5) . . . . ?
O2 C1 C9 F1 -149.6(4) . . . . ?
O2 C1 C9 C10 89.5(4) . . . . ?
C1 C2 C3 C4 179.8(4) . . . . ?
C1 C2 C6 C7 179.3(4) . . . . ?
C1 C9 C10 C11 -56.5(5) . . . . ?
C1 C9 C10 C15 124.0(4) . . . . ?
C2 C1 C9 P1 147.2(3) . . . . ?
C2 C1 C9 F1 31.8(5) . . . . ?
C2 C1 C9 C10 -89.1(4) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
C2 C6 C7 C5 0.8(8) . . . . ?
C3 C2 C6 C7 -1.2(7) . . . . ?
C3 C4 C5 C7 -1.3(8) . . . . ?
C3 C4 C5 C8 177.6(5) . . . . ?
C4 C5 C7 C6 0.4(8) . . . . ?
C6 C2 C3 C4 0.3(6) . . . . ?
C8 C5 C7 C6 -178.5(5) . . . . ?
C9 P1 C16 C17 99.4(4) . . . . ?
C9 P1 C16 C21 -79.2(3) . . . . ?
C9 P1 C22 C23 155.0(4) . . . . ?
C9 P1 C22 C27 -26.1(4) . . . . ?
C9 C1 C2 C3 20.0(6) . . . . ?
C9 C1 C2 C6 -160.5(4) . . . . ?
C9 C10 C11 C12 -177.4(4) . . . . ?
C9 C10 C15 C14 178.0(5) . . . . ?
C10 C11 C12 C13 -2.3(9) . . . . ?
C11 C10 C15 C14 -1.4(8) . . . . ?
C11 C12 C13 C14 1.8(10) . . . . ?
C12 C13 C14 C15 -1.1(11) . . . . ?
C13 C14 C15 C10 0.9(10) . . . . ?
C15 C10 C11 C12 2.1(7) . . . . ?
C16 P1 C9 F1 -45.6(3) . . . . ?
C16 P1 C9 C1 -163.2(3) . . . . ?
C16 P1 C9 C10 72.9(3) . . . . ?
C16 P1 C22 C23 -97.7(4) . . . . ?
C16 P1 C22 C27 81.2(4) . . . . ?
C16 C17 C18 C19 1.5(7) . . . . ?
C17 C16 C21 C20 -0.9(6) . . . . ?
C17 C18 C19 C20 -1.5(7) . . . . ?
C18 C19 C20 C21 0.3(7) . . . . ?
C19 C20 C21 C16 0.9(7) . . . . ?
C21 C16 C17 C18 -0.3(7) . . . . ?
C22 P1 C9 F1 66.7(3) . . . . ?
C22 P1 C9 C1 -50.9(3) . . . . ?
C22 P1 C9 C10 -174.9(3) . . . . ?
C22 P1 C16 C17 -11.7(4) . . . . ?
C22 P1 C16 C21 169.7(3) . . . . ?
C22 C23 C24 C25 0.9(9) . . . . ?
C23 C22 C27 C26 -1.8(8) . . . . ?
C23 C24 C25 C26 -1.7(10) . . . . ?
C24 C25 C26 C27 0.8(9) . . . . ?
C25 C26 C27 C22 1.0(8) . . . . ?
C27 C22 C23 C24 0.8(8) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 -0.126 0.500 268.7 63.7 ?

_olex2_date_sample_data_collection 2020-06-22
_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 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.719
####################################################################### 
# 
# 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_xieshl_0715
_database_code_depnum_ccdc_archive 'CCDC 2034806'
loop_
_audit_author_name
_audit_author_address
'Xie Shaolei' 'Lanzhou University'
_audit_update_record             
;
2020-09-30 deposited with the CCDC.	2020-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-07-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H Cl3, C27 H22 F O2 P'
_chemical_formula_sum            'C28 H23 Cl3 F O2 P'
_chemical_formula_weight         547.78
_chemical_absolute_configuration ad
_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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.9203(2)
_cell_length_b                   9.7787(2)
_cell_length_c                   13.8908(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.935(2)
_cell_angle_gamma                90
_cell_volume                     1307.85(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6001
_cell_measurement_temperature    172.90(10)
_cell_measurement_theta_max      69.8150
_cell_measurement_theta_min      9.6150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44062
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10492
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        66.582
_diffrn_reflns_theta_max         66.582
_diffrn_reflns_theta_min         4.592
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.90(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 110.00   1.00    1.00    --   54.00  57.00  60.00   74
  2  ω     87.00 115.00   1.00    1.00    --  108.00  50.00 -30.00   28
  3  ω    118.00 178.00   1.00    1.00    --  108.00  77.00 -60.00   60
  4  ω    146.00 172.00   1.00    1.00    --  108.00  44.00 -94.54   26
  5  ω    148.00 174.00   1.00    1.00    --  108.00  50.00-150.00   26
  6  ω    121.00 177.00   1.00    1.00    --  108.00  77.00-180.00   56
  7  ω    140.00 178.00   1.00    1.00    --  108.00  50.00 -30.00   38
  8  ω     96.00 122.00   1.00    1.00    --  108.00  50.00-120.00   26
  9  ω     87.00 113.00   1.00    1.00    --  108.00  50.00 -60.00   26
 10  ω     86.00 112.00   1.00    1.00    --  108.00  63.00 -60.00   26
 11  ω     84.00 110.00   1.00    1.00    --  108.00  38.00 -60.00   26
 12  ω     86.00 112.00   1.00    1.00    --  108.00  63.00 -30.00   26
 13  ω     78.00 103.00   1.00    1.00    --  108.00  77.00 -60.00   25
 14  ω     82.00 112.00   1.00    1.00    --  108.00  38.00 -30.00   30
 15  ω     82.00 176.00   1.00    1.00    --  108.00  38.00   0.00   94
 16  ω     87.00 113.00   1.00    1.00    --  108.00  50.00-150.00   26
 17  ω     89.00 150.00   1.00    1.00    --  108.00  63.00-120.00   61
 18  ω     83.00 113.00   1.00    1.00    --  108.00  69.00-152.78   30
 19  ω     79.00 105.00   1.00    1.00    --  108.00  77.00-120.00   26
 20  ω     84.00 110.00   1.00    1.00    --  108.00  38.00 -90.00   26
 21  ω     83.00 108.00   1.00    1.00    --  108.00  38.00-120.00   25
 22  ω     80.00 106.00   1.00    1.00    --  108.00  77.00-150.00   26
 23  ω     79.00 177.00   1.00    1.00    --  108.00  75.00-101.76   98
 24  ω     85.00 111.00   1.00    1.00    --  108.00  44.00 -94.54   26
 25  ω     78.00 104.00   1.00    1.00    --  108.00  77.00 -90.00   26
 26  ω     78.00 104.00   1.00    1.00    --  108.00  77.00 -30.00   26
 27  ω     77.00 109.00   1.00    1.00    --  108.00  25.00 -90.00   32
 28  ω     55.00 136.00   1.00    1.00    --  108.00 -25.00-180.00   81
 29  ω     76.00 102.00   1.00    1.00    --  108.00-111.00-120.00   26
 30  ω     57.00 129.00   1.00    1.00    --  108.00 -63.00-150.00   72
 31  ω     44.00  70.00   1.00    1.00    --  108.00-111.00-120.00   26
 32  ω     23.00  65.00   1.00    1.00    --   54.00 -38.00-150.00   42
 33  ω     41.00  68.00   1.00    1.00    --    0.00   0.00 -60.00   27
 34  ω     32.00 118.00   1.00    1.00    --   54.00  19.00  30.00   86
 35  ω     54.00  86.00   1.00    1.00    --   54.00  77.00 -60.00   32
 36  ω     32.00  98.00   1.00    1.00    --   54.00  77.00 -90.00   66
 37  ω     29.00  54.00   1.00    1.00    --    0.00  77.00   0.00   25
 38  ω     24.00  57.00   1.00    1.00    --   54.00  77.00-120.00   33
 39  ω     65.00 115.00   1.00    1.00    --  108.00 178.00 -30.00   50
 40  ω    -20.00  12.00   1.00    1.00    --    0.00  77.00   0.00   32
 41  ω    -10.00  69.00   1.00    1.00    --   54.00 -57.00  90.00   79
 42  ω     36.00  78.00   1.00    1.00    --  108.00-111.00 120.00   42
 43  ω    -55.00  -7.00   1.00    1.00    --    0.00 -57.00 -30.00   48
 44  ω     -5.00  71.00   1.00    1.00    --   54.00 -57.00-180.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1586424000
_diffrn_orient_matrix_UB_12      0.0062077000
_diffrn_orient_matrix_UB_13      -0.0137028000
_diffrn_orient_matrix_UB_21      0.0153066000
_diffrn_orient_matrix_UB_22      -0.0647216000
_diffrn_orient_matrix_UB_23      0.1031376000
_diffrn_orient_matrix_UB_31      0.0139304000
_diffrn_orient_matrix_UB_32      0.1435442000
_diffrn_orient_matrix_UB_33      0.0472349000
_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         0.809
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                4335
_reflns_number_total             4451
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1854 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(9)
_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     317
_refine_ls_number_reflns         4451
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.047
_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)+(0.0656P)²+0.5059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl -0.75766(13) -0.22260(19) -0.52166(11) 0.0662(5) Uani 1 1 d . . . . .
Cl2 Cl -1.01860(15) -0.1849(2) -0.65811(12) 0.0776(5) Uani 1 1 d . . . . .
Cl3 Cl -0.9305(3) 0.0100(2) -0.50311(15) 0.0902(7) Uani 1 1 d . . . . .
C28 C -0.8757(5) -0.1002(6) -0.5837(3) 0.0422(11) Uani 1 1 d . . . . .
H28 H -0.830740 -0.046334 -0.626643 0.051 Uiso 1 1 calc R U . . .
P1 P -0.30541(8) -0.45441(10) -0.18244(6) 0.0174(2) Uani 1 1 d . . . . .
F3 F -0.5681(2) -0.4859(2) -0.17845(14) 0.0207(5) Uani 1 1 d . . . . .
O1 O -0.2137(3) -0.4317(3) -0.25088(19) 0.0255(6) Uani 1 1 d . . . . .
O2 O -0.4341(3) -0.1904(3) -0.2531(2) 0.0269(6) Uani 1 1 d . . . . .
C1 C -0.4944(3) -0.4219(4) -0.2409(2) 0.0171(7) Uani 1 1 d . . . . .
C2 C -0.5269(3) -0.2680(4) -0.2463(2) 0.0181(7) Uani 1 1 d . . . . .
C3 C -0.6680(3) -0.2186(4) -0.2434(2) 0.0186(7) Uani 1 1 d . . . . .
C4 C -0.7860(4) -0.3027(4) -0.2658(3) 0.0235(8) Uani 1 1 d . . . . .
H4 H -0.778477 -0.394205 -0.282015 0.028 Uiso 1 1 calc R U . . .
C5 C -0.9155(4) -0.2472(5) -0.2634(3) 0.0271(9) Uani 1 1 d . . . . .
H5 H -0.994076 -0.302492 -0.278068 0.033 Uiso 1 1 calc R U . . .
C6 C -0.9278(4) -0.1110(5) -0.2394(3) 0.0288(9) Uani 1 1 d . . . . .
C7 C -0.8100(4) -0.0295(5) -0.2180(3) 0.0307(9) Uani 1 1 d . . . . .
H7 H -0.817534 0.062001 -0.201857 0.037 Uiso 1 1 calc R U . . .
C8 C -0.6809(4) -0.0823(4) -0.2205(3) 0.0261(8) Uani 1 1 d . . . . .
H8 H -0.603037 -0.026001 -0.206637 0.031 Uiso 1 1 calc R U . . .
C9 C -1.0675(5) -0.0511(6) -0.2378(4) 0.0466(13) Uani 1 1 d . . . . .
H9A H -1.107388 -0.008856 -0.300571 0.070 Uiso 1 1 calc R U . . .
H9B H -1.056087 0.016051 -0.186084 0.070 Uiso 1 1 calc R U . . .
H9C H -1.127795 -0.122534 -0.225771 0.070 Uiso 1 1 calc R U . . .
C10 C -0.5379(4) -0.4839(4) -0.3441(2) 0.0217(8) Uani 1 1 d . . . . .
C11 C -0.6321(4) -0.5900(5) -0.3644(3) 0.0330(9) Uani 1 1 d . . . . .
H11 H -0.667059 -0.627737 -0.313912 0.040 Uiso 1 1 calc R U . . .
C12 C -0.6748(5) -0.6405(6) -0.4605(4) 0.0488(14) Uani 1 1 d . . . . .
H12 H -0.738701 -0.711680 -0.474501 0.059 Uiso 1 1 calc R U . . .
C13 C -0.6215(6) -0.5844(7) -0.5356(3) 0.0514(15) Uani 1 1 d . . . . .
H13 H -0.651484 -0.616864 -0.600174 0.062 Uiso 1 1 calc R U . . .
C14 C -0.5256(6) -0.4819(6) -0.5151(3) 0.0467(14) Uani 1 1 d . . . . .
H14 H -0.488426 -0.446889 -0.565376 0.056 Uiso 1 1 calc R U . . .
C15 C -0.4832(5) -0.4296(5) -0.4199(3) 0.0326(10) Uani 1 1 d . . . . .
H15 H -0.418752 -0.358881 -0.406413 0.039 Uiso 1 1 calc R U . . .
C16 C -0.3083(3) -0.6307(4) -0.1444(3) 0.0188(7) Uani 1 1 d . . . . .
C17 C -0.3304(4) -0.7298(4) -0.2181(3) 0.0230(8) Uani 1 1 d . . . . .
H17 H -0.341754 -0.703981 -0.284042 0.028 Uiso 1 1 calc R U . . .
C18 C -0.3356(4) -0.8669(4) -0.1943(3) 0.0278(8) Uani 1 1 d . . . . .
H18 H -0.353328 -0.932385 -0.244331 0.033 Uiso 1 1 calc R U . . .
C19 C -0.3143(4) -0.9064(5) -0.0962(3) 0.0295(9) Uani 1 1 d . . . . .
H19 H -0.316676 -0.998548 -0.080080 0.035 Uiso 1 1 calc R U . . .
C20 C -0.2895(4) -0.8080(5) -0.0218(3) 0.0310(9) Uani 1 1 d . . . . .
H20 H -0.274027 -0.834548 0.044236 0.037 Uiso 1 1 calc R U . . .
C21 C -0.2878(4) -0.6699(5) -0.0459(3) 0.0251(8) Uani 1 1 d . . . . .
H21 H -0.273024 -0.604096 0.003935 0.030 Uiso 1 1 calc R U . . .
C22 C -0.2634(4) -0.3490(4) -0.0724(3) 0.0209(7) Uani 1 1 d . . . . .
C23 C -0.1307(4) -0.2950(5) -0.0439(3) 0.0307(9) Uani 1 1 d . . . . .
H23 H -0.065104 -0.316006 -0.079493 0.037 Uiso 1 1 calc R U . . .
C24 C -0.0961(4) -0.2092(6) 0.0384(3) 0.0412(11) Uani 1 1 d . . . . .
H24 H -0.006668 -0.173848 0.058295 0.049 Uiso 1 1 calc R U . . .
C25 C -0.1942(5) -0.1761(5) 0.0907(3) 0.0372(10) Uani 1 1 d . . . . .
H25 H -0.171609 -0.116686 0.144421 0.045 Uiso 1 1 calc R U . . .
C26 C -0.3248(4) -0.2315(5) 0.0628(3) 0.0318(9) Uani 1 1 d . . . . .
H26 H -0.390180 -0.210540 0.098579 0.038 Uiso 1 1 calc R U . . .
C27 C -0.3601(4) -0.3178(5) -0.0176(3) 0.0278(9) Uani 1 1 d . . . . .
H27 H -0.448742 -0.355498 -0.035412 0.033 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
Cl1 C28 1.750(5) . ?
Cl2 C28 1.748(6) . ?
Cl3 C28 1.733(5) . ?
C28 H28 0.9800 . ?
P1 O1 1.482(2) . ?
P1 C1 1.882(3) . ?
P1 C16 1.805(4) . ?
P1 C22 1.807(4) . ?
F3 C1 1.408(4) . ?
O2 C2 1.215(4) . ?
C1 C2 1.537(5) . ?
C1 C10 1.520(5) . ?
C2 C3 1.490(5) . ?
C3 C4 1.403(5) . ?
C3 C8 1.384(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(6) . ?
C6 C7 1.387(6) . ?
C6 C9 1.509(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(5) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.380(6) . ?
C10 C15 1.400(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.364(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(5) . ?
C16 C21 1.389(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.393(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.384(5) . ?
C22 C27 1.395(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.393(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.386(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.371(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.376(6) . ?
C27 H27 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
Cl1 C28 H28 108.6 . . ?
Cl2 C28 Cl1 108.6(3) . . ?
Cl2 C28 H28 108.6 . . ?
Cl3 C28 Cl1 112.6(3) . . ?
Cl3 C28 Cl2 109.9(3) . . ?
Cl3 C28 H28 108.6 . . ?
O1 P1 C1 113.55(15) . . ?
O1 P1 C16 112.73(16) . . ?
O1 P1 C22 113.87(17) . . ?
C16 P1 C1 101.70(15) . . ?
C16 P1 C22 108.33(17) . . ?
C22 P1 C1 105.73(16) . . ?
F3 C1 P1 105.7(2) . . ?
F3 C1 C2 109.4(3) . . ?
F3 C1 C10 109.4(3) . . ?
C2 C1 P1 111.2(2) . . ?
C10 C1 P1 111.5(2) . . ?
C10 C1 C2 109.6(3) . . ?
O2 C2 C1 117.5(3) . . ?
O2 C2 C3 122.3(3) . . ?
C3 C2 C1 120.2(3) . . ?
C4 C3 C2 122.9(3) . . ?
C8 C3 C2 117.3(3) . . ?
C8 C3 C4 119.8(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 C9 120.7(4) . . ?
C7 C6 C9 120.2(4) . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.1(4) . . ?
C8 C7 H7 119.5 . . ?
C3 C8 C7 120.0(4) . . ?
C3 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 121.1(3) . . ?
C11 C10 C15 119.8(4) . . ?
C15 C10 C1 119.0(3) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(5) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(5) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(5) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 120.2 . . ?
C14 C15 C10 119.6(5) . . ?
C14 C15 H15 120.2 . . ?
C17 C16 P1 117.5(3) . . ?
C17 C16 C21 119.6(4) . . ?
C21 C16 P1 122.9(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.8(4) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 119.8(4) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 P1 118.0(3) . . ?
C23 C22 C27 119.5(4) . . ?
C27 C22 P1 122.5(3) . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.6(4) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.7(4) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.7(4) . . ?
C27 C26 H26 119.7 . . ?
C22 C27 H27 119.9 . . ?
C26 C27 C22 120.2(4) . . ?
C26 C27 H27 119.9 . . ?

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 C1 C2 O2 29.0(4) . . . . ?
P1 C1 C2 C3 -151.1(2) . . . . ?
P1 C1 C10 C11 114.2(4) . . . . ?
P1 C1 C10 C15 -67.1(4) . . . . ?
P1 C16 C17 C18 -179.2(3) . . . . ?
P1 C16 C21 C20 -179.1(3) . . . . ?
P1 C22 C23 C24 177.6(4) . . . . ?
P1 C22 C27 C26 -176.8(3) . . . . ?
F3 C1 C2 O2 145.3(3) . . . . ?
F3 C1 C2 C3 -34.8(4) . . . . ?
F3 C1 C10 C11 -2.3(5) . . . . ?
F3 C1 C10 C15 176.3(3) . . . . ?
O1 P1 C1 F3 162.8(2) . . . . ?
O1 P1 C1 C2 -78.6(3) . . . . ?
O1 P1 C1 C10 44.1(3) . . . . ?
O1 P1 C16 C17 -49.2(3) . . . . ?
O1 P1 C16 C21 129.9(3) . . . . ?
O1 P1 C22 C23 -21.5(4) . . . . ?
O1 P1 C22 C27 156.9(3) . . . . ?
O2 C2 C3 C4 160.0(3) . . . . ?
O2 C2 C3 C8 -17.9(5) . . . . ?
C1 P1 C16 C17 72.8(3) . . . . ?
C1 P1 C16 C21 -108.1(3) . . . . ?
C1 P1 C22 C23 -146.9(3) . . . . ?
C1 P1 C22 C27 31.5(4) . . . . ?
C1 C2 C3 C4 -19.9(5) . . . . ?
C1 C2 C3 C8 162.2(3) . . . . ?
C1 C10 C11 C12 177.1(4) . . . . ?
C1 C10 C15 C14 -177.8(4) . . . . ?
C2 C1 C10 C11 -122.2(4) . . . . ?
C2 C1 C10 C15 56.4(4) . . . . ?
C2 C3 C4 C5 -178.6(3) . . . . ?
C2 C3 C8 C7 179.0(3) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C3 C8 C7 1.0(6) . . . . ?
C4 C5 C6 C7 0.3(6) . . . . ?
C4 C5 C6 C9 179.4(4) . . . . ?
C5 C6 C7 C8 0.0(6) . . . . ?
C6 C7 C8 C3 -0.7(6) . . . . ?
C8 C3 C4 C5 -0.7(5) . . . . ?
C9 C6 C7 C8 -179.1(4) . . . . ?
C10 C1 C2 O2 -94.8(4) . . . . ?
C10 C1 C2 C3 85.1(4) . . . . ?
C10 C11 C12 C13 0.4(7) . . . . ?
C11 C10 C15 C14 0.9(6) . . . . ?
C11 C12 C13 C14 1.3(7) . . . . ?
C12 C13 C14 C15 -2.0(7) . . . . ?
C13 C14 C15 C10 0.9(7) . . . . ?
C15 C10 C11 C12 -1.5(6) . . . . ?
C16 P1 C1 F3 41.5(2) . . . . ?
C16 P1 C1 C2 160.1(2) . . . . ?
C16 P1 C1 C10 -77.3(3) . . . . ?
C16 P1 C22 C23 104.8(3) . . . . ?
C16 P1 C22 C27 -76.9(4) . . . . ?
C16 C17 C18 C19 -2.0(5) . . . . ?
C17 C16 C21 C20 0.0(5) . . . . ?
C17 C18 C19 C20 0.8(6) . . . . ?
C18 C19 C20 C21 0.9(6) . . . . ?
C19 C20 C21 C16 -1.3(6) . . . . ?
C21 C16 C17 C18 1.6(5) . . . . ?
C22 P1 C1 F3 -71.6(2) . . . . ?
C22 P1 C1 C2 47.0(3) . . . . ?
C22 P1 C1 C10 169.6(2) . . . . ?
C22 P1 C16 C17 -176.1(3) . . . . ?
C22 P1 C16 C21 3.0(3) . . . . ?
C22 C23 C24 C25 -0.9(7) . . . . ?
C23 C22 C27 C26 1.6(6) . . . . ?
C23 C24 C25 C26 1.9(7) . . . . ?
C24 C25 C26 C27 -1.1(7) . . . . ?
C25 C26 C27 C22 -0.6(7) . . . . ?
C27 C22 C23 C24 -0.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.041
_oxdiff_exptl_absorpt_empirical_full_min 0.544
####################################################################### 
# 
# 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_xieshl_284-7
_database_code_depnum_ccdc_archive 'CCDC 2034802'
loop_
_audit_author_name
_audit_author_address
'Xie Shaolei' 'Lanzhou University'
_audit_update_record             
;
2020-09-30 deposited with the CCDC.	2020-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-09-28
_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         'C26 H19 Br F O2 P'
_chemical_formula_sum            'C26 H19 Br F O2 P'
_chemical_formula_weight         493.29
_chemical_absolute_configuration ad
_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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.20266(14)
_cell_length_b                   17.5076(3)
_cell_length_c                   19.9155(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2162.71(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2152
_cell_measurement_temperature    293.30(10)
_cell_measurement_theta_max      69.6550
_cell_measurement_theta_min      10.0880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.539
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62837
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4949
_diffrn_reflns_point_group_measured_fraction_full 0.851
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        66.571
_diffrn_reflns_theta_max         66.571
_diffrn_reflns_theta_min         4.440
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.30(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    101.00 173.00   1.00    1.00    --  108.00 111.00  60.00   72
  2  ω     86.00 170.00   1.00    1.00    --  108.00  38.00-120.00   84
  3  ω     87.00 126.00   1.00    1.00    --   54.00  38.00-180.00   39
  4  ω     72.00 117.00   1.00    1.00    --   54.00  57.00 -90.00   45
  5  ω     26.00  51.00   1.00    1.00    --    0.00  57.00-180.00   25
  6  ω     -5.00  22.00   1.00    1.00    --    0.00  57.00-120.00   27
  7  ω    -19.00  17.00   1.00    1.00    --    0.00  57.00-180.00   36
  8  ω     53.00 120.00   1.00    1.00    --  108.00 -50.00  90.00   67
  9  ω     81.00 112.00   1.00    1.00    --  108.00-111.00 -90.00   31
 10  ω     68.00 101.00   1.00    1.00    --  108.00-111.00-150.00   33
 11  ω     58.00  84.00   1.00    1.00    --   54.00-125.00-150.00   26
 12  ω    -11.00  72.00   1.00    1.00    --   54.00 -57.00-150.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0152831000
_diffrn_orient_matrix_UB_12      0.0415201000
_diffrn_orient_matrix_UB_13      -0.0680583000
_diffrn_orient_matrix_UB_21      -0.0165863000
_diffrn_orient_matrix_UB_22      -0.0775211000
_diffrn_orient_matrix_UB_23      -0.0362132000
_diffrn_orient_matrix_UB_31      -0.2473127000
_diffrn_orient_matrix_UB_32      0.0027011000
_diffrn_orient_matrix_UB_33      0.0066173000
_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         0.465
_reflns_Friedel_fraction_full    0.644
_reflns_Friedel_fraction_max     0.644
_reflns_number_gt                2931
_reflns_number_total             3261
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.040
_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)+(0.0452P)²+0.0900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0877
_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:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br 1.06720(12) 0.19813(3) 0.56650(3) 0.0794(2) Uani 1 1 d . . . . .
P1 P 0.49027(16) 0.62100(6) 0.71262(5) 0.0381(2) Uani 1 1 d . . . . .
F1 F 0.8430(4) 0.56805(13) 0.65716(13) 0.0445(6) Uani 1 1 d . . . . .
O1 O 0.2549(5) 0.6292(2) 0.70475(18) 0.0585(9) Uani 1 1 d . . . . .
O2 O 0.3548(5) 0.47123(18) 0.6594(2) 0.0640(10) Uani 1 1 d . . . . .
C1 C 0.6208(6) 0.5650(2) 0.6437(2) 0.0369(9) Uani 1 1 d . . . . .
C2 C 0.5428(7) 0.4813(2) 0.6445(2) 0.0414(10) Uani 1 1 d . . . . .
C3 C 0.6815(7) 0.4159(2) 0.6256(2) 0.0376(9) Uani 1 1 d . . . . .
C4 C 0.5939(8) 0.3435(2) 0.6353(2) 0.0475(10) Uani 1 1 d . . . . .
H4 H 0.457533 0.338740 0.654247 0.057 Uiso 1 1 calc R U . . .
C5 C 0.7056(9) 0.2789(2) 0.6172(2) 0.0550(13) Uani 1 1 d . . . . .
H5 H 0.646077 0.230684 0.623672 0.066 Uiso 1 1 calc R U . . .
C6 C 0.9084(9) 0.2870(2) 0.5893(2) 0.0515(11) Uani 1 1 d . . . . .
C7 C 0.9969(8) 0.3575(3) 0.5781(2) 0.0529(11) Uani 1 1 d . . . . .
H7 H 1.131844 0.361671 0.558115 0.064 Uiso 1 1 calc R U . . .
C8 C 0.8853(7) 0.4222(2) 0.5966(2) 0.0487(11) Uani 1 1 d . . . . .
H8 H 0.945989 0.470120 0.589641 0.058 Uiso 1 1 calc R U . . .
C9 C 0.5794(7) 0.6008(2) 0.5757(2) 0.0390(9) Uani 1 1 d . . . . .
C10 C 0.7402(8) 0.6443(3) 0.5452(2) 0.0488(11) Uani 1 1 d . . . . .
H10 H 0.872609 0.651065 0.566280 0.059 Uiso 1 1 calc R U . . .
C11 C 0.7011(10) 0.6776(3) 0.4830(2) 0.0629(14) Uani 1 1 d . . . . .
H11 H 0.808240 0.706541 0.462531 0.076 Uiso 1 1 calc R U . . .
C12 C 0.5070(11) 0.6682(3) 0.4517(2) 0.0667(15) Uani 1 1 d . . . . .
H12 H 0.483195 0.690306 0.409833 0.080 Uiso 1 1 calc R U . . .
C13 C 0.3478(10) 0.6265(3) 0.4817(3) 0.0655(14) Uani 1 1 d . . . . .
H13 H 0.215690 0.620454 0.460281 0.079 Uiso 1 1 calc R U . . .
C14 C 0.3820(8) 0.5931(3) 0.5440(2) 0.0522(11) Uani 1 1 d . . . . .
H14 H 0.272097 0.565416 0.564470 0.063 Uiso 1 1 calc R U . . .
C15 C 0.6200(7) 0.7131(2) 0.71105(19) 0.0381(9) Uani 1 1 d . . . . .
C16 C 0.8253(7) 0.7277(2) 0.7346(2) 0.0429(10) Uani 1 1 d . . . . .
H16 H 0.911948 0.687478 0.748893 0.052 Uiso 1 1 calc R U . . .
C17 C 0.9033(8) 0.8019(2) 0.7373(2) 0.0518(11) Uani 1 1 d . . . . .
H17 H 1.041016 0.811364 0.753701 0.062 Uiso 1 1 calc R U . . .
C18 C 0.7765(9) 0.8615(3) 0.7155(2) 0.0581(13) Uani 1 1 d . . . . .
H18 H 0.828317 0.911278 0.717533 0.070 Uiso 1 1 calc R U . . .
C19 C 0.5747(10) 0.8476(3) 0.6909(2) 0.0603(13) Uani 1 1 d . . . . .
H19 H 0.490633 0.887952 0.675551 0.072 Uiso 1 1 calc R U . . .
C20 C 0.4945(8) 0.7737(3) 0.6887(2) 0.0492(11) Uani 1 1 d . . . . .
H20 H 0.356498 0.764778 0.672228 0.059 Uiso 1 1 calc R U . . .
C21 C 0.5690(7) 0.5743(2) 0.7900(2) 0.0393(9) Uani 1 1 d . . . . .
C22 C 0.7712(8) 0.5437(2) 0.8035(2) 0.0520(11) Uani 1 1 d . . . . .
H22 H 0.877829 0.544306 0.770646 0.062 Uiso 1 1 calc R U . . .
C23 C 0.8134(10) 0.5124(3) 0.8659(3) 0.0588(13) Uani 1 1 d . . . . .
H23 H 0.947986 0.491125 0.874484 0.071 Uiso 1 1 calc R U . . .
C24 C 0.6603(12) 0.5124(3) 0.9150(3) 0.0689(17) Uani 1 1 d . . . . .
H24 H 0.691268 0.492134 0.957045 0.083 Uiso 1 1 calc R U . . .
C25 C 0.4597(11) 0.5426(3) 0.9021(3) 0.0669(16) Uani 1 1 d . . . . .
H25 H 0.356163 0.542666 0.935852 0.080 Uiso 1 1 calc R U . . .
C26 C 0.4091(9) 0.5728(2) 0.8398(2) 0.0501(11) Uani 1 1 d . . . . .
H26 H 0.271791 0.591764 0.831204 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
Br1 C6 1.896(4) . ?
P1 O1 1.475(3) . ?
P1 C1 1.871(4) . ?
P1 C15 1.802(4) . ?
P1 C21 1.812(4) . ?
F1 C1 1.405(4) . ?
O2 C2 1.216(5) . ?
C1 C2 1.544(5) . ?
C1 C9 1.514(6) . ?
C2 C3 1.481(6) . ?
C3 C4 1.392(6) . ?
C3 C8 1.395(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(7) . ?
C6 C7 1.369(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(6) . ?
C9 C14 1.384(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.366(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(6) . ?
C15 C20 1.390(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.377(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.366(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(7) . ?
C21 C26 1.403(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.363(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.375(9) . ?
C25 H25 0.9300 . ?
C25 C26 1.384(7) . ?
C26 H26 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 C1 113.67(19) . . ?
O1 P1 C15 110.7(2) . . ?
O1 P1 C21 113.6(2) . . ?
C15 P1 C1 105.22(18) . . ?
C15 P1 C21 107.33(18) . . ?
C21 P1 C1 105.73(18) . . ?
F1 C1 P1 105.4(3) . . ?
F1 C1 C2 110.0(3) . . ?
F1 C1 C9 108.7(3) . . ?
C2 C1 P1 110.7(3) . . ?
C9 C1 P1 111.5(3) . . ?
C9 C1 C2 110.4(3) . . ?
O2 C2 C1 116.2(4) . . ?
O2 C2 C3 120.4(4) . . ?
C3 C2 C1 123.4(4) . . ?
C4 C3 C2 116.3(4) . . ?
C4 C3 C8 118.9(4) . . ?
C8 C3 C2 124.8(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.7(4) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 Br1 119.0(3) . . ?
C7 C6 Br1 119.5(4) . . ?
C7 C6 C5 121.5(4) . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.8(4) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 120.1(4) . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C1 119.6(4) . . ?
C14 C9 C1 121.2(4) . . ?
C14 C9 C10 119.2(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(5) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(5) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(5) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.1(5) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 P1 124.9(3) . . ?
C16 C15 C20 118.9(4) . . ?
C20 C15 P1 116.0(3) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.5(4) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.9(5) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.1(4) . . ?
C19 C20 H20 119.9 . . ?
C22 C21 P1 125.5(3) . . ?
C22 C21 C26 119.6(4) . . ?
C26 C21 P1 114.8(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.8(5) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.8(5) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.8(5) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.4 . . ?
C24 C25 C26 121.3(5) . . ?
C26 C25 H25 119.4 . . ?
C21 C26 H26 120.7 . . ?
C25 C26 C21 118.7(5) . . ?
C25 C26 H26 120.7 . . ?

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
Br1 C6 C7 C8 -177.9(4) . . . . ?
P1 C1 C2 O2 36.6(5) . . . . ?
P1 C1 C2 C3 -146.1(3) . . . . ?
P1 C1 C9 C10 101.6(4) . . . . ?
P1 C1 C9 C14 -76.5(4) . . . . ?
P1 C15 C16 C17 -173.7(3) . . . . ?
P1 C15 C20 C19 174.7(3) . . . . ?
P1 C21 C22 C23 177.2(3) . . . . ?
P1 C21 C26 C25 -176.0(3) . . . . ?
F1 C1 C2 O2 152.6(4) . . . . ?
F1 C1 C2 C3 -30.0(5) . . . . ?
F1 C1 C9 C10 -14.2(5) . . . . ?
F1 C1 C9 C14 167.8(4) . . . . ?
O1 P1 C1 F1 175.9(3) . . . . ?
O1 P1 C1 C2 -65.2(3) . . . . ?
O1 P1 C1 C9 58.1(3) . . . . ?
O1 P1 C15 C16 161.6(4) . . . . ?
O1 P1 C15 C20 -13.5(4) . . . . ?
O1 P1 C21 C22 164.4(4) . . . . ?
O1 P1 C21 C26 -18.0(4) . . . . ?
O2 C2 C3 C4 -8.8(7) . . . . ?
O2 C2 C3 C8 168.1(5) . . . . ?
C1 P1 C15 C16 -75.2(4) . . . . ?
C1 P1 C15 C20 109.7(3) . . . . ?
C1 P1 C21 C22 39.0(4) . . . . ?
C1 P1 C21 C26 -143.4(3) . . . . ?
C1 C2 C3 C4 173.9(4) . . . . ?
C1 C2 C3 C8 -9.2(7) . . . . ?
C1 C9 C10 C11 -179.5(4) . . . . ?
C1 C9 C14 C13 179.9(4) . . . . ?
C2 C1 C9 C10 -134.9(4) . . . . ?
C2 C1 C9 C14 47.1(5) . . . . ?
C2 C3 C4 C5 177.7(4) . . . . ?
C2 C3 C8 C7 -177.0(4) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C4 C3 C8 C7 -0.2(7) . . . . ?
C4 C5 C6 Br1 178.3(3) . . . . ?
C4 C5 C6 C7 -1.4(7) . . . . ?
C5 C6 C7 C8 1.8(7) . . . . ?
C6 C7 C8 C3 -1.0(7) . . . . ?
C8 C3 C4 C5 0.6(7) . . . . ?
C9 C1 C2 O2 -87.4(5) . . . . ?
C9 C1 C2 C3 90.0(5) . . . . ?
C9 C10 C11 C12 0.2(7) . . . . ?
C10 C9 C14 C13 1.9(7) . . . . ?
C10 C11 C12 C13 0.7(8) . . . . ?
C11 C12 C13 C14 -0.3(8) . . . . ?
C12 C13 C14 C9 -1.0(7) . . . . ?
C14 C9 C10 C11 -1.4(6) . . . . ?
C15 P1 C1 F1 54.7(3) . . . . ?
C15 P1 C1 C2 173.5(3) . . . . ?
C15 P1 C1 C9 -63.1(3) . . . . ?
C15 P1 C21 C22 -72.9(4) . . . . ?
C15 P1 C21 C26 104.7(3) . . . . ?
C15 C16 C17 C18 -0.8(7) . . . . ?
C16 C15 C20 C19 -0.7(6) . . . . ?
C16 C17 C18 C19 -0.5(7) . . . . ?
C17 C18 C19 C20 1.1(7) . . . . ?
C18 C19 C20 C15 -0.5(7) . . . . ?
C20 C15 C16 C17 1.3(6) . . . . ?
C21 P1 C1 F1 -58.7(3) . . . . ?
C21 P1 C1 C2 60.1(3) . . . . ?
C21 P1 C1 C9 -176.5(3) . . . . ?
C21 P1 C15 C16 37.1(4) . . . . ?
C21 P1 C15 C20 -138.0(3) . . . . ?
C21 C22 C23 C24 -1.2(7) . . . . ?
C22 C21 C26 C25 1.8(6) . . . . ?
C22 C23 C24 C25 1.2(8) . . . . ?
C23 C24 C25 C26 0.3(8) . . . . ?
C24 C25 C26 C21 -1.8(7) . . . . ?
C26 C21 C22 C23 -0.3(7) . . . . ?

_olex2_date_sample_data_collection 2020-09-25
_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 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.740
####################################################################### 
# 
# 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_xieshl_245-91
_database_code_depnum_ccdc_archive 'CCDC 2034801'
loop_
_audit_author_name
_audit_author_address
'Xie Shaolei' 'Lanzhou University'
_audit_update_record             
;
2020-09-30 deposited with the CCDC.	2020-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-09-28
_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         'C26 H20 F O2 P'
_chemical_formula_sum            'C26 H20 F O2 P'
_chemical_formula_weight         414.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.2255(5)
_cell_length_b                   12.6121(7)
_cell_length_c                   18.2822(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2127.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1659
_cell_measurement_temperature    293.57(10)
_cell_measurement_theta_max      68.4380
_cell_measurement_theta_min      4.2450
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    1.380
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78875
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5258
_diffrn_reflns_point_group_measured_fraction_full 0.820
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        66.565
_diffrn_reflns_theta_max         66.565
_diffrn_reflns_theta_min         4.259
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.57(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  37.00   1.00    1.00    --    0.00  57.00  30.00   28
  2  ω     36.00 121.00   1.00    1.00    --   54.00  57.00 120.00   85
  3  ω    149.00 176.00   1.00    1.50    --  108.00 111.00 150.00   27
  4  ω     48.00 133.00   1.00    1.50    --  108.00 -77.00  60.00   85
  5  ω    105.00 133.00   1.00    1.50    --  108.00 -38.00-120.00   28
  6  ω     37.00  77.00   1.00    1.50    --  108.00 -38.00-120.00   40
  7  ω     24.00  66.00   1.00    1.00    --   54.00-125.00-150.00   42
  8  ω     23.00  54.00   1.00    1.00    --   54.00-125.00 -90.00   31
  9  ω    -19.00  16.00   1.00    1.00    --    0.00 -57.00-120.00   35
 10  ω    -69.00 -37.00   1.00    1.00    --    0.00 -57.00-120.00   32
 11  ω      2.00  56.00   1.00    1.00    --   54.00 -99.00 120.00   54
 12  ω     38.00 125.00   1.00    1.50    --  108.00 -38.00 150.00   87
 13  ω    100.00 146.00   1.00    1.50    --  108.00 111.00-120.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0471230000
_diffrn_orient_matrix_UB_12      0.0654028000
_diffrn_orient_matrix_UB_13      -0.0670771000
_diffrn_orient_matrix_UB_21      -0.0961290000
_diffrn_orient_matrix_UB_22      -0.0925535000
_diffrn_orient_matrix_UB_23      -0.0257299000
_diffrn_orient_matrix_UB_31      -0.1279863000
_diffrn_orient_matrix_UB_32      0.0454973000
_diffrn_orient_matrix_UB_33      0.0442008000
_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         0.436
_reflns_Friedel_fraction_full    0.582
_reflns_Friedel_fraction_max     0.582
_reflns_number_gt                2726
_reflns_number_total             3076
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.269
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 704 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0810
_refine_ls_restrained_S_all      1.085
_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)+(0.1530P)²+1.0880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2258
_refine_ls_wR_factor_ref         0.2369
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C7) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C4(H4), C5(H5), C6(H6), C10(H10), C14(H14), C13(H13),
 C12(H12), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22),
  C23(H23), C24(H24), C25(H25), C26(H26)
3.b Fitted hexagon refined as free rotating group:
 C7(C8,C3,C4,C5,C6), C10(C9,C14,C13,C12,C11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.45491(18) -0.37597(12) -0.21084(10) 0.0459(5) Uani 1 1 d . . . . .
F1 F -0.4205(4) -0.5687(3) -0.1589(2) 0.0528(10) Uani 1 1 d . . . . .
O1 O -0.4835(6) -0.2660(4) -0.1872(3) 0.0594(14) Uani 1 1 d . . . . .
O2 O -0.7232(6) -0.4131(4) -0.1214(4) 0.0723(17) Uani 1 1 d . . . . .
C1 C -0.4833(7) -0.4762(6) -0.1353(4) 0.0468(15) Uani 1 1 d . . . . .
C2 C -0.6456(8) -0.4906(6) -0.1197(4) 0.0511(17) Uani 1 1 d . . . . .
C7 C -0.6881(7) -0.7781(3) -0.0646(3) 0.076(3) Uani 1 1 d G U . . .
H7 H -0.632949 -0.834276 -0.046882 0.091 Uiso 1 1 calc R U . . .
C8 C -0.6230(5) -0.6807(4) -0.0784(3) 0.0589(19) Uani 1 1 d G . . . .
H8 H -0.524430 -0.671715 -0.069872 0.071 Uiso 1 1 calc R U . . .
C3 C -0.7054(5) -0.5968(3) -0.1049(3) 0.0518(17) Uani 1 1 d G . . . .
C4 C -0.8528(5) -0.6103(4) -0.1177(3) 0.070(2) Uani 1 1 d G . . . .
H4 H -0.907903 -0.554214 -0.135404 0.084 Uiso 1 1 calc R U . . .
C5 C -0.9178(5) -0.7077(5) -0.1039(4) 0.085(3) Uani 1 1 d G U . . .
H5 H -1.016425 -0.716774 -0.112414 0.103 Uiso 1 1 calc R U . . .
C6 C -0.8354(7) -0.7916(4) -0.0774(3) 0.084(3) Uani 1 1 d G U . . .
H6 H -0.878951 -0.856805 -0.068153 0.101 Uiso 1 1 calc R U . . .
C10 C -0.2654(6) -0.4752(4) -0.0506(3) 0.075(3) Uani 1 1 d G . . . .
H10 H -0.226005 -0.528954 -0.079127 0.090 Uiso 1 1 calc R U . . .
C9 C -0.4028(5) -0.4360(4) -0.0662(3) 0.0539(17) Uani 1 1 d G . . . .
C14 C -0.4617(5) -0.3556(5) -0.0235(3) 0.070(2) Uani 1 1 d G . . . .
H14 H -0.553582 -0.329406 -0.034008 0.084 Uiso 1 1 calc R U . . .
C13 C -0.3833(8) -0.3145(5) 0.0349(3) 0.095(3) Uani 1 1 d G U . . .
H13 H -0.422686 -0.260728 0.063438 0.114 Uiso 1 1 calc R U . . .
C12 C -0.2459(8) -0.3537(5) 0.0505(3) 0.091(3) Uani 1 1 d G U . . .
H12 H -0.193450 -0.326162 0.089603 0.110 Uiso 1 1 calc R U . . .
C11 C -0.1870(5) -0.4340(5) 0.0078(4) 0.085(3) Uani 1 1 d G U . . .
H11 H -0.095108 -0.460275 0.018322 0.102 Uiso 1 1 calc R U . . .
C15 C -0.5633(7) -0.4187(5) -0.2875(4) 0.0470(14) Uani 1 1 d . . . . .
C16 C -0.5803(8) -0.5240(5) -0.3088(4) 0.0486(16) Uani 1 1 d . . . . .
H16 H -0.538279 -0.578115 -0.281536 0.058 Uiso 1 1 calc R U . . .
C17 C -0.6601(9) -0.5474(7) -0.3706(4) 0.064(2) Uani 1 1 d . . . . .
H17 H -0.674239 -0.617797 -0.384024 0.077 Uiso 1 1 calc R U . . .
C18 C -0.7196(9) -0.4670(8) -0.4130(5) 0.070(2) Uani 1 1 d . . . . .
H18 H -0.771255 -0.482691 -0.455294 0.084 Uiso 1 1 calc R U . . .
C19 C -0.7007(9) -0.3667(9) -0.3916(5) 0.072(2) Uani 1 1 d . . . . .
H19 H -0.740362 -0.313317 -0.420393 0.086 Uiso 1 1 calc R U . . .
C20 C -0.6261(8) -0.3372(6) -0.3293(5) 0.0583(19) Uani 1 1 d . . . . .
H20 H -0.617788 -0.266450 -0.315568 0.070 Uiso 1 1 calc R U . . .
C21 C -0.2661(7) -0.3982(6) -0.2349(4) 0.0507(17) Uani 1 1 d . . . . .
C22 C -0.2203(9) -0.4848(7) -0.2740(5) 0.064(2) Uani 1 1 d . . . . .
H22 H -0.287522 -0.532846 -0.292387 0.077 Uiso 1 1 calc R U . . .
C23 C -0.0741(10) -0.5002(9) -0.2861(6) 0.080(2) Uani 1 1 d . . . . .
H23 H -0.042818 -0.559816 -0.311525 0.096 Uiso 1 1 calc R U . . .
C24 C 0.0226(9) -0.4301(10) -0.2614(5) 0.079(3) Uani 1 1 d . . . . .
H24 H 0.120765 -0.441817 -0.269616 0.095 Uiso 1 1 calc R U . . .
C25 C -0.0195(10) -0.3430(10) -0.2248(7) 0.089(3) Uani 1 1 d . . . . .
H25 H 0.049366 -0.294420 -0.208664 0.106 Uiso 1 1 calc R U . . .
C26 C -0.1646(9) -0.3253(7) -0.2111(5) 0.068(2) Uani 1 1 d . . . . .
H26 H -0.193939 -0.264808 -0.186007 0.082 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 1.477(5) . ?
P1 C1 1.890(7) . ?
P1 C15 1.803(7) . ?
P1 C21 1.819(7) . ?
F1 C1 1.373(8) . ?
O2 C2 1.212(9) . ?
C1 C2 1.535(10) . ?
C1 C9 1.550(8) . ?
C2 C3 1.474(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.3900 . ?
C7 C6 1.3900 . ?
C8 H8 0.9300 . ?
C8 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C6 1.3900 . ?
C6 H6 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.3900 . ?
C10 C11 1.3900 . ?
C9 C14 1.3900 . ?
C14 H14 0.9300 . ?
C14 C13 1.3900 . ?
C13 H13 0.9300 . ?
C13 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C11 1.3900 . ?
C11 H11 0.9300 . ?
C15 C16 1.393(9) . ?
C15 C20 1.406(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(10) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(12) . ?
C18 H18 0.9300 . ?
C18 C19 1.336(14) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(11) . ?
C21 C26 1.382(11) . ?
C22 H22 0.9300 . ?
C22 C23 1.380(13) . ?
C23 H23 0.9300 . ?
C23 C24 1.334(14) . ?
C24 H24 0.9300 . ?
C24 C25 1.344(15) . ?
C25 H25 0.9300 . ?
C25 C26 1.380(14) . ?
C26 H26 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 C1 112.9(3) . . ?
O1 P1 C15 114.2(3) . . ?
O1 P1 C21 112.7(3) . . ?
C15 P1 C1 106.9(3) . . ?
C15 P1 C21 107.3(3) . . ?
C21 P1 C1 101.9(3) . . ?
F1 C1 P1 106.2(4) . . ?
F1 C1 C2 111.7(6) . . ?
F1 C1 C9 109.4(5) . . ?
C2 C1 P1 110.5(5) . . ?
C2 C1 C9 110.8(6) . . ?
C9 C1 P1 108.1(4) . . ?
O2 C2 C1 118.4(7) . . ?
O2 C2 C3 121.1(6) . . ?
C3 C2 C1 120.5(6) . . ?
C8 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C3 120.0 . . ?
C3 C8 H8 120.0 . . ?
C8 C3 C2 123.4(4) . . ?
C8 C3 C4 120.0 . . ?
C4 C3 C2 116.6(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C9 C1 119.3(4) . . ?
C14 C9 C1 120.6(4) . . ?
C14 C9 C10 120.0 . . ?
C9 C14 H14 120.0 . . ?
C9 C14 C13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C16 C15 P1 124.4(5) . . ?
C16 C15 C20 119.9(7) . . ?
C20 C15 P1 115.6(5) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(7) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.7(8) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.8 . . ?
C19 C18 C17 118.5(8) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 H19 117.9 . . ?
C18 C19 C20 124.1(9) . . ?
C20 C19 H19 117.9 . . ?
C15 C20 H20 121.4 . . ?
C19 C20 C15 117.2(8) . . ?
C19 C20 H20 121.4 . . ?
C22 C21 P1 122.9(6) . . ?
C22 C21 C26 119.0(7) . . ?
C26 C21 P1 118.0(6) . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.7(8) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.4(10) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.1(9) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.2(9) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 120.3 . . ?
C25 C26 C21 119.5(9) . . ?
C25 C26 H26 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 O2 -38.7(9) . . . . ?
P1 C1 C2 C3 139.7(5) . . . . ?
P1 C1 C9 C10 -97.7(4) . . . . ?
P1 C1 C9 C14 77.3(5) . . . . ?
P1 C15 C16 C17 -176.8(6) . . . . ?
P1 C15 C20 C19 175.2(6) . . . . ?
P1 C21 C22 C23 -175.6(8) . . . . ?
P1 C21 C26 C25 176.3(8) . . . . ?
F1 C1 C2 O2 -156.7(7) . . . . ?
F1 C1 C2 C3 21.7(9) . . . . ?
F1 C1 C9 C10 17.6(6) . . . . ?
F1 C1 C9 C14 -167.5(4) . . . . ?
O1 P1 C1 F1 -165.8(4) . . . . ?
O1 P1 C1 C2 72.9(6) . . . . ?
O1 P1 C1 C9 -48.5(5) . . . . ?
O1 P1 C15 C16 -164.6(6) . . . . ?
O1 P1 C15 C20 19.0(7) . . . . ?
O1 P1 C21 C22 -164.3(6) . . . . ?
O1 P1 C21 C26 17.1(7) . . . . ?
O2 C2 C3 C8 -157.8(7) . . . . ?
O2 C2 C3 C4 21.1(9) . . . . ?
C1 P1 C15 C16 -39.1(7) . . . . ?
C1 P1 C15 C20 144.6(6) . . . . ?
C1 P1 C21 C22 74.4(7) . . . . ?
C1 P1 C21 C26 -104.1(7) . . . . ?
C1 C2 C3 C8 23.9(9) . . . . ?
C1 C2 C3 C4 -157.2(6) . . . . ?
C1 C9 C14 C13 -174.9(5) . . . . ?
C2 C1 C9 C10 141.1(5) . . . . ?
C2 C1 C9 C14 -43.9(7) . . . . ?
C2 C3 C4 C5 -178.9(5) . . . . ?
C7 C8 C3 C2 178.8(6) . . . . ?
C7 C8 C3 C4 0.0 . . . . ?
C8 C7 C6 C5 0.0 . . . . ?
C8 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C6 C7 C8 C3 0.0 . . . . ?
C10 C9 C14 C13 0.0 . . . . ?
C9 C1 C2 O2 81.1(8) . . . . ?
C9 C1 C2 C3 -100.6(7) . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C9 C14 C13 C12 0.0 . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
C13 C12 C11 C10 0.0 . . . . ?
C11 C10 C9 C1 175.0(5) . . . . ?
C11 C10 C9 C14 0.0 . . . . ?
C15 P1 C1 F1 67.8(5) . . . . ?
C15 P1 C1 C2 -53.4(6) . . . . ?
C15 P1 C1 C9 -174.8(4) . . . . ?
C15 P1 C21 C22 -37.7(7) . . . . ?
C15 P1 C21 C26 143.7(6) . . . . ?
C15 C16 C17 C18 2.1(12) . . . . ?
C16 C15 C20 C19 -1.3(11) . . . . ?
C16 C17 C18 C19 -1.6(13) . . . . ?
C17 C18 C19 C20 -0.4(14) . . . . ?
C18 C19 C20 C15 1.8(14) . . . . ?
C20 C15 C16 C17 -0.6(11) . . . . ?
C21 P1 C1 F1 -44.6(5) . . . . ?
C21 P1 C1 C2 -165.9(5) . . . . ?
C21 P1 C1 C9 72.7(5) . . . . ?
C21 P1 C15 C16 69.7(7) . . . . ?
C21 P1 C15 C20 -106.7(6) . . . . ?
C21 C22 C23 C24 -1.6(16) . . . . ?
C22 C21 C26 C25 -2.3(13) . . . . ?
C22 C23 C24 C25 -0.4(17) . . . . ?
C23 C24 C25 C26 1.0(17) . . . . ?
C24 C25 C26 C21 0.4(16) . . . . ?
C26 C21 C22 C23 2.9(13) . . . . ?

_olex2_date_sample_data_collection 2020-09-25
_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.778
####################################################################### 
# 
# 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_xieshl_284-8
_database_code_depnum_ccdc_archive 'CCDC 2034803'
loop_
_audit_author_name
_audit_author_address
'Xie Shaolei' 'Lanzhou University'
_audit_update_record             
;
2020-09-30 deposited with the CCDC.	2020-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-09-30
_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         'C26 H19 Br F O2 P'
_chemical_formula_sum            'C26 H19 Br F O2 P'
_chemical_formula_weight         493.29
_chemical_absolute_configuration ad
_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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.2073(3)
_cell_length_b                   17.5063(6)
_cell_length_c                   19.9264(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2165.31(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1814
_cell_measurement_temperature    293.44(10)
_cell_measurement_theta_max      68.9330
_cell_measurement_theta_min      5.0310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79802
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5000
_diffrn_reflns_point_group_measured_fraction_full 0.829
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        66.556
_diffrn_reflns_theta_max         66.556
_diffrn_reflns_theta_min         4.438
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.44(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  58.00   1.00    1.00    --    0.00  57.00 120.00   27
  2  ω     33.00 123.00   1.00    2.00    --   54.00  57.00 -30.00   90
  3  ω    136.00 174.00   1.00    3.00    --  108.00  38.00 -30.00   38
  4  ω    118.00 144.00   1.00    3.00    --  108.00 107.00  62.00   26
  5  ω    118.00 144.00   1.00    3.00    --  108.00 111.00 120.00   26
  6  ω     39.00 130.00   1.00    3.00    --  108.00 -50.00 150.00   91
  7  ω     41.00  97.00   1.00    3.00    --  108.00-111.00 120.00   56
  8  ω     40.00 129.00   1.00    3.00    --  108.00 -63.00 -90.00   89
  9  ω     47.00 104.00   1.00    2.00    --   54.00-125.00-120.00   57
 10  ω     66.00  93.00   1.00    2.00    --   54.00  57.00-180.00   27
 11  ω    -66.00 -14.00   1.00    1.00    --    0.00 -57.00 150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0389473000
_diffrn_orient_matrix_UB_12      0.0832283000
_diffrn_orient_matrix_UB_13      -0.0220141000
_diffrn_orient_matrix_UB_21      0.0794462000
_diffrn_orient_matrix_UB_22      0.0196862000
_diffrn_orient_matrix_UB_23      0.0712082000
_diffrn_orient_matrix_UB_31      0.2318256000
_diffrn_orient_matrix_UB_32      -0.0206600000
_diffrn_orient_matrix_UB_33      -0.0206757000
_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         0.465
_reflns_Friedel_fraction_full    0.628
_reflns_Friedel_fraction_max     0.628
_reflns_number_gt                2650
_reflns_number_total             3181
_reflns_odcompleteness_completeness 97.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 731 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.044(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      0.991
_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)+(0.0305P)²+0.0956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0778
_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:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br -0.06758(12) -0.19831(3) -0.06649(4) 0.0808(2) Uani 1 1 d . . . . .
P1 P 0.50978(18) -0.62110(6) -0.21252(6) 0.0396(3) Uani 1 1 d . . . . .
F1 F 0.1570(4) -0.56824(14) -0.15734(14) 0.0451(6) Uani 1 1 d . . . . .
O1 O 0.6444(5) -0.47157(19) -0.1595(2) 0.0662(11) Uani 1 1 d . . . . .
O2 O 0.7455(5) -0.6290(2) -0.20442(18) 0.0590(9) Uani 1 1 d . . . . .
C1 C 0.3798(7) -0.5648(2) -0.1435(2) 0.0379(10) Uani 1 1 d . . . . .
C2 C 0.4567(7) -0.4814(2) -0.1446(2) 0.0414(10) Uani 1 1 d . . . . .
C3 C 0.3184(7) -0.4159(2) -0.1257(2) 0.0398(11) Uani 1 1 d . . . . .
C4 C 0.1155(8) -0.4222(3) -0.0970(3) 0.0492(12) Uani 1 1 d . . . . .
H4 H 0.054642 -0.470165 -0.090384 0.059 Uiso 1 1 calc R U . . .
C5 C 0.0039(8) -0.3576(2) -0.0783(2) 0.0529(12) Uani 1 1 d . . . . .
H5 H -0.130672 -0.361980 -0.058186 0.063 Uiso 1 1 calc R U . . .
C6 C 0.0913(9) -0.2867(2) -0.0894(2) 0.0507(12) Uani 1 1 d . . . . .
C7 C 0.2940(9) -0.2790(3) -0.1175(2) 0.0568(14) Uani 1 1 d . . . . .
H7 H 0.353963 -0.230940 -0.124055 0.068 Uiso 1 1 calc R U . . .
C8 C 0.4046(9) -0.3437(2) -0.1354(2) 0.0489(12) Uani 1 1 d . . . . .
H8 H 0.540733 -0.338947 -0.154396 0.059 Uiso 1 1 calc R U . . .
C9 C 0.4206(7) -0.6010(2) -0.0756(2) 0.0393(10) Uani 1 1 d . . . . .
C10 C 0.6173(9) -0.5928(3) -0.0441(2) 0.0533(13) Uani 1 1 d . . . . .
H10 H 0.726587 -0.564925 -0.064560 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6520(10) -0.6262(3) 0.0183(3) 0.0666(15) Uani 1 1 d . . . . .
H11 H 0.783971 -0.619993 0.039664 0.080 Uiso 1 1 calc R U . . .
C12 C 0.4932(11) -0.6680(3) 0.0482(3) 0.0668(17) Uani 1 1 d . . . . .
H12 H 0.517744 -0.690332 0.089895 0.080 Uiso 1 1 calc R U . . .
C13 C 0.2982(11) -0.6772(3) 0.0173(3) 0.0644(16) Uani 1 1 d . . . . .
H13 H 0.190572 -0.705672 0.037989 0.077 Uiso 1 1 calc R U . . .
C14 C 0.2600(9) -0.6438(3) -0.0456(2) 0.0504(12) Uani 1 1 d . . . . .
H14 H 0.127955 -0.650343 -0.066931 0.061 Uiso 1 1 calc R U . . .
C15 C 0.4319(8) -0.5740(2) -0.2899(2) 0.0430(10) Uani 1 1 d . . . . .
C16 C 0.2306(9) -0.5436(3) -0.3035(2) 0.0518(12) Uani 1 1 d . . . . .
H16 H 0.123579 -0.544232 -0.270893 0.062 Uiso 1 1 calc R U . . .
C17 C 0.1898(11) -0.5126(3) -0.3657(3) 0.0623(16) Uani 1 1 d . . . . .
H17 H 0.055560 -0.491043 -0.374202 0.075 Uiso 1 1 calc R U . . .
C18 C 0.3420(12) -0.5127(3) -0.4152(3) 0.0702(19) Uani 1 1 d . . . . .
H18 H 0.310092 -0.492810 -0.457310 0.084 Uiso 1 1 calc R U . . .
C19 C 0.5437(12) -0.5424(3) -0.4022(3) 0.0710(18) Uani 1 1 d . . . . .
H19 H 0.648708 -0.542056 -0.435437 0.085 Uiso 1 1 calc R U . . .
C20 C 0.5900(9) -0.5728(2) -0.3396(3) 0.0534(12) Uani 1 1 d . . . . .
H20 H 0.726296 -0.592461 -0.330770 0.064 Uiso 1 1 calc R U . . .
C21 C 0.3814(7) -0.7133(2) -0.2113(2) 0.0380(10) Uani 1 1 d . . . . .
C22 C 0.1744(8) -0.7279(3) -0.2346(2) 0.0434(11) Uani 1 1 d . . . . .
H22 H 0.087408 -0.687630 -0.248479 0.052 Uiso 1 1 calc R U . . .
C23 C 0.0971(9) -0.8019(3) -0.2372(2) 0.0533(12) Uani 1 1 d . . . . .
H23 H -0.040810 -0.811220 -0.253487 0.064 Uiso 1 1 calc R U . . .
C24 C 0.2227(10) -0.8618(3) -0.2158(3) 0.0598(15) Uani 1 1 d . . . . .
H24 H 0.171505 -0.911635 -0.218330 0.072 Uiso 1 1 calc R U . . .
C25 C 0.4249(10) -0.8473(3) -0.1907(3) 0.0626(15) Uani 1 1 d . . . . .
H25 H 0.508843 -0.887530 -0.175105 0.075 Uiso 1 1 calc R U . . .
C26 C 0.5047(8) -0.7740(3) -0.1882(2) 0.0505(12) Uani 1 1 d . . . . .
H26 H 0.641786 -0.765130 -0.171095 0.061 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
Br1 C6 1.891(4) . ?
P1 O2 1.479(3) . ?
P1 C1 1.875(4) . ?
P1 C15 1.813(5) . ?
P1 C21 1.800(4) . ?
F1 C1 1.412(5) . ?
O1 C2 1.215(6) . ?
C1 C2 1.535(5) . ?
C1 C9 1.514(6) . ?
C2 C3 1.481(6) . ?
C3 C4 1.388(7) . ?
C3 C8 1.386(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(6) . ?
C6 C7 1.383(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(6) . ?
C9 C14 1.383(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.365(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.368(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.404(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(7) . ?
C15 C20 1.395(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.365(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.389(6) . ?
C21 C26 1.388(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.374(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.375(8) . ?
C25 H25 0.9300 . ?
C25 C26 1.376(7) . ?
C26 H26 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
O2 P1 C1 113.3(2) . . ?
O2 P1 C15 113.5(2) . . ?
O2 P1 C21 110.6(2) . . ?
C15 P1 C1 105.7(2) . . ?
C21 P1 C1 105.72(19) . . ?
C21 P1 C15 107.5(2) . . ?
F1 C1 P1 104.8(3) . . ?
F1 C1 C2 110.0(3) . . ?
F1 C1 C9 108.7(4) . . ?
C2 C1 P1 110.8(3) . . ?
C9 C1 P1 111.3(3) . . ?
C9 C1 C2 111.1(4) . . ?
O1 C2 C1 115.9(4) . . ?
O1 C2 C3 120.5(4) . . ?
C3 C2 C1 123.5(4) . . ?
C4 C3 C2 124.7(4) . . ?
C4 C3 C8 118.7(4) . . ?
C8 C3 C2 116.6(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 Br1 119.7(4) . . ?
C5 C6 C7 120.9(4) . . ?
C7 C6 Br1 119.5(4) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.7(5) . . ?
C8 C7 H7 120.6 . . ?
C3 C8 H8 119.2 . . ?
C7 C8 C3 121.6(5) . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C1 120.7(4) . . ?
C10 C9 C14 119.8(4) . . ?
C14 C9 C1 119.5(4) . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(5) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 119.3(5) . . ?
C9 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 P1 125.6(4) . . ?
C16 C15 C20 119.3(5) . . ?
C20 C15 P1 115.0(4) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.7(5) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.5(6) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.5(5) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.1(6) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 119.9(6) . . ?
C19 C20 H20 120.0 . . ?
C22 C21 P1 124.7(3) . . ?
C26 C21 P1 116.5(3) . . ?
C26 C21 C22 118.7(4) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(4) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.4(5) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.3(5) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 120.9(5) . . ?
C26 C25 H25 119.5 . . ?
C21 C26 H26 119.9 . . ?
C25 C26 C21 120.2(5) . . ?
C25 C26 H26 119.9 . . ?

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
Br1 C6 C7 C8 -178.3(4) . . . . ?
P1 C1 C2 O1 -36.9(6) . . . . ?
P1 C1 C2 C3 146.0(4) . . . . ?
P1 C1 C9 C10 77.3(4) . . . . ?
P1 C1 C9 C14 -101.7(4) . . . . ?
P1 C15 C16 C17 -176.9(4) . . . . ?
P1 C15 C20 C19 176.1(4) . . . . ?
P1 C21 C22 C23 174.0(4) . . . . ?
P1 C21 C26 C25 -174.8(4) . . . . ?
F1 C1 C2 O1 -152.3(5) . . . . ?
F1 C1 C2 C3 30.6(6) . . . . ?
F1 C1 C9 C10 -167.8(4) . . . . ?
F1 C1 C9 C14 13.2(5) . . . . ?
O1 C2 C3 C4 -168.3(5) . . . . ?
O1 C2 C3 C8 8.9(7) . . . . ?
O2 P1 C1 F1 -175.9(3) . . . . ?
O2 P1 C1 C2 65.4(4) . . . . ?
O2 P1 C1 C9 -58.6(4) . . . . ?
O2 P1 C15 C16 -164.4(4) . . . . ?
O2 P1 C15 C20 18.9(4) . . . . ?
O2 P1 C21 C22 -162.4(4) . . . . ?
O2 P1 C21 C26 14.3(4) . . . . ?
C1 P1 C15 C16 -39.6(4) . . . . ?
C1 P1 C15 C20 143.6(3) . . . . ?
C1 P1 C21 C22 74.6(4) . . . . ?
C1 P1 C21 C26 -108.7(4) . . . . ?
C1 C2 C3 C4 8.6(7) . . . . ?
C1 C2 C3 C8 -174.1(4) . . . . ?
C1 C9 C10 C11 179.7(4) . . . . ?
C1 C9 C14 C13 -179.9(4) . . . . ?
C2 C1 C9 C10 -46.7(5) . . . . ?
C2 C1 C9 C14 134.4(4) . . . . ?
C2 C3 C4 C5 176.8(5) . . . . ?
C2 C3 C8 C7 -177.6(5) . . . . ?
C3 C4 C5 C6 1.4(8) . . . . ?
C4 C3 C8 C7 -0.3(7) . . . . ?
C4 C5 C6 Br1 177.7(4) . . . . ?
C4 C5 C6 C7 -1.9(8) . . . . ?
C5 C6 C7 C8 1.3(8) . . . . ?
C6 C7 C8 C3 -0.2(8) . . . . ?
C8 C3 C4 C5 -0.3(7) . . . . ?
C9 C1 C2 O1 87.3(6) . . . . ?
C9 C1 C2 C3 -89.8(5) . . . . ?
C9 C10 C11 C12 0.8(8) . . . . ?
C10 C9 C14 C13 1.1(7) . . . . ?
C10 C11 C12 C13 -0.2(8) . . . . ?
C11 C12 C13 C14 0.1(8) . . . . ?
C12 C13 C14 C9 -0.6(7) . . . . ?
C14 C9 C10 C11 -1.3(7) . . . . ?
C15 P1 C1 F1 59.2(3) . . . . ?
C15 P1 C1 C2 -59.4(3) . . . . ?
C15 P1 C1 C9 176.5(3) . . . . ?
C15 P1 C21 C22 -37.9(4) . . . . ?
C15 P1 C21 C26 138.8(4) . . . . ?
C15 C16 C17 C18 1.7(8) . . . . ?
C16 C15 C20 C19 -0.9(7) . . . . ?
C16 C17 C18 C19 -2.0(9) . . . . ?
C17 C18 C19 C20 0.8(8) . . . . ?
C18 C19 C20 C15 0.6(8) . . . . ?
C20 C15 C16 C17 -0.2(7) . . . . ?
C21 P1 C1 F1 -54.6(3) . . . . ?
C21 P1 C1 C2 -173.3(3) . . . . ?
C21 P1 C1 C9 62.7(3) . . . . ?
C21 P1 C15 C16 72.9(4) . . . . ?
C21 P1 C15 C20 -103.9(4) . . . . ?
C21 C22 C23 C24 1.0(7) . . . . ?
C22 C21 C26 C25 2.1(7) . . . . ?
C22 C23 C24 C25 1.1(8) . . . . ?
C23 C24 C25 C26 -1.7(8) . . . . ?
C24 C25 C26 C21 0.0(8) . . . . ?
C26 C21 C22 C23 -2.6(7) . . . . ?

_olex2_date_sample_data_collection 2020-09-25
_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 1.585
_oxdiff_exptl_absorpt_empirical_full_min 0.802
####################################################################### 
# 
# 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_xieshl_308_3
_database_code_depnum_ccdc_archive 'CCDC 2034804'
loop_
_audit_author_name
_audit_author_address
'Xie Shaolei' 'Lanzhou University'
_audit_update_record             
;
2020-09-30 deposited with the CCDC.	2020-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-08-19
_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         'C27 H22 F O2 P'
_chemical_formula_sum            'C27 H22 F O2 P'
_chemical_formula_weight         428.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.4706(7)
_cell_length_b                   12.3535(14)
_cell_length_c                   19.120(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2236.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2173
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.3070
_cell_measurement_theta_min      4.6570
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    1.328
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38664
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5293
_diffrn_reflns_point_group_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         4.261
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     83.00 178.00   1.00    2.50    --  108.00  38.00  60.00   95
  2  ω     77.00 110.00   1.00    2.50    --  108.00  25.00-120.00   33
  3  ω     82.00 148.00   1.00    2.50    --  108.00  38.00-180.00   66
  4  ω     69.00 121.00   1.00    1.00    --   54.00  57.00-180.00   52
  5  ω     37.00  69.00   1.00    1.00    --    0.00  57.00-180.00   32
  6  ω     41.00 124.00   1.00    1.00    --   54.00  77.00-120.00   83
  7  ω    121.00 148.00   1.00    2.50    --  108.00 178.00-180.00   27
  8  ω     64.00  91.00   1.00    2.50    --  108.00 178.00-180.00   27
  9  ω    -67.00 -42.00   1.00    1.00    --    0.00 150.00 -50.00   25
 10  ω    -50.00  -5.00   1.00    1.00    --    0.00 -57.00-120.00   45
 11  ω     42.00 103.00   1.00    1.00    --   54.00-125.00 -30.00   61
 12  ω     36.00 116.00   1.00    2.50    --  108.00-111.00 120.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1462359000
_diffrn_orient_matrix_UB_12      0.0417664000
_diffrn_orient_matrix_UB_13      0.0228298000
_diffrn_orient_matrix_UB_21      0.0366014000
_diffrn_orient_matrix_UB_22      0.0255912000
_diffrn_orient_matrix_UB_23      -0.0766777000
_diffrn_orient_matrix_UB_31      -0.0613628000
_diffrn_orient_matrix_UB_32      0.1147586000
_diffrn_orient_matrix_UB_33      0.0088368000
_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         0.555
_reflns_Friedel_fraction_full    0.733
_reflns_Friedel_fraction_max     0.733
_reflns_number_gt                2774
_reflns_number_total             3477
_reflns_odcompleteness_completeness 98.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 858 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.098
_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)+(0.0777P)²+0.9837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1728
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C26(H26), C19(H19), C25(H25), C20(H20), C10(H10), C14(H14), C6(H6), C5(H5),
 C4(H4), C3(H3), C2(H2), C17(H17), C13(H13), C21(H21), C18(H18), C24(H24),
 C27(H27), C23(H23), C11(H11)
2.b Fitted hexagon refined as free rotating group:
 C6(C5,C4,C3,C2,C1)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.40330(15) 0.53908(11) 0.23486(9) 0.0614(4) Uani 1 1 d . . . . .
F1 F 0.5235(4) 0.3833(2) 0.16245(18) 0.0705(9) Uani 1 1 d . . . . .
O1 O 0.2880(5) 0.5690(5) 0.0931(3) 0.1051(18) Uani 1 1 d . . . . .
O2 O 0.3717(5) 0.6557(3) 0.2364(3) 0.0770(12) Uani 1 1 d . . . . .
C26 C -0.0022(7) 0.4494(6) 0.2704(4) 0.0861(19) Uani 1 1 d . . . . .
H26 H -0.085067 0.485116 0.282573 0.103 Uiso 1 1 calc R U . . .
C19 C 0.7140(7) 0.4665(8) 0.4144(4) 0.090(2) Uani 1 1 d . . . . .
H19 H 0.773212 0.453932 0.452297 0.109 Uiso 1 1 calc R U . . .
C25 C -0.0032(7) 0.3399(6) 0.2615(4) 0.0839(19) Uani 1 1 d . . . . .
H25 H -0.086785 0.301248 0.266911 0.101 Uiso 1 1 calc R U . . .
C8 C 0.4845(6) 0.4928(4) 0.1508(3) 0.0617(14) Uani 1 1 d . . . . .
C20 C 0.6722(6) 0.3827(6) 0.3728(3) 0.0726(17) Uani 1 1 d . . . . .
H20 H 0.705159 0.313125 0.381743 0.087 Uiso 1 1 calc R U . . .
C10 C 0.6025(7) 0.6623(5) 0.1092(3) 0.0689(15) Uani 1 1 d . . . . .
H10 H 0.514347 0.695441 0.108939 0.083 Uiso 1 1 calc R U . . .
C14 C 0.7473(6) 0.5098(6) 0.1323(4) 0.0799(19) Uani 1 1 d . . . . .
H14 H 0.758208 0.438690 0.147349 0.096 Uiso 1 1 calc R U . . .
C6 C 0.4980(4) 0.3550(4) 0.0154(2) 0.089(2) Uani 1 1 d G . . . .
H6 H 0.576311 0.355660 0.044732 0.106 Uiso 1 1 calc R U . . .
C5 C 0.4962(6) 0.2883(4) -0.0431(3) 0.105(3) Uani 1 1 d G . . . .
H5 H 0.573440 0.244287 -0.052956 0.126 Uiso 1 1 calc R U . . .
C4 C 0.3792(8) 0.2873(5) -0.0869(2) 0.124(4) Uani 1 1 d G . . . .
H4 H 0.378005 0.242609 -0.126106 0.149 Uiso 1 1 calc R U . . .
C3 C 0.2638(6) 0.3530(6) -0.0722(3) 0.139(4) Uani 1 1 d G . . . .
H3 H 0.185439 0.352303 -0.101568 0.167 Uiso 1 1 calc R U . . .
C2 C 0.2655(5) 0.4197(5) -0.0137(3) 0.110(3) Uani 1 1 d G . . . .
H2 H 0.188306 0.463677 -0.003881 0.132 Uiso 1 1 calc R U . . .
C1 C 0.3826(5) 0.4207(4) 0.0301(2) 0.0728(17) Uani 1 1 d G . . . .
C12 C 0.8535(7) 0.6741(7) 0.0878(4) 0.085(2) Uani 1 1 d . . . . .
C9 C 0.6146(6) 0.5559(5) 0.1312(3) 0.0619(14) Uani 1 1 d . . . . .
C17 C 0.5764(7) 0.5895(5) 0.3443(4) 0.0799(19) Uani 1 1 d . . . . .
H17 H 0.545635 0.659592 0.335232 0.096 Uiso 1 1 calc R U . . .
C13 C 0.8637(7) 0.5682(7) 0.1112(4) 0.090(2) Uani 1 1 d . . . . .
H13 H 0.952089 0.535486 0.112759 0.108 Uiso 1 1 calc R U . . .
C7 C 0.3752(6) 0.4967(5) 0.0905(4) 0.0704(16) Uani 1 1 d . . . . .
C15 C 0.9800(9) 0.7357(9) 0.0628(5) 0.126(3) Uani 1 1 d . . . . .
H15A H 0.990399 0.726091 0.013271 0.188 Uiso 1 1 calc R U . . .
H15B H 1.062900 0.709222 0.086169 0.188 Uiso 1 1 calc R U . . .
H15C H 0.967928 0.811166 0.073081 0.188 Uiso 1 1 calc R U . . .
C21 C 0.5804(7) 0.4007(5) 0.3170(3) 0.0656(15) Uani 1 1 d . . . . .
H21 H 0.552098 0.342792 0.289216 0.079 Uiso 1 1 calc R U . . .
C22 C 0.2470(5) 0.4551(5) 0.2453(3) 0.0618(13) Uani 1 1 d . . . . .
C18 C 0.6675(8) 0.5710(7) 0.3998(5) 0.100(3) Uani 1 1 d . . . . .
H18 H 0.697758 0.628618 0.427298 0.120 Uiso 1 1 calc R U . . .
C24 C 0.1195(8) 0.2868(6) 0.2444(4) 0.093(2) Uani 1 1 d . . . . .
H24 H 0.118320 0.212400 0.237224 0.111 Uiso 1 1 calc R U . . .
C27 C 0.1219(6) 0.5083(5) 0.2613(4) 0.0775(17) Uani 1 1 d . . . . .
H27 H 0.120928 0.583227 0.266020 0.093 Uiso 1 1 calc R U . . .
C23 C 0.2455(7) 0.3438(5) 0.2379(4) 0.0791(18) Uani 1 1 d . . . . .
H23 H 0.329025 0.306906 0.228575 0.095 Uiso 1 1 calc R U . . .
C11 C 0.7192(7) 0.7197(6) 0.0879(4) 0.0784(18) Uani 1 1 d . . . . .
H11 H 0.708054 0.790931 0.073170 0.094 Uiso 1 1 calc R U . . .
C16 C 0.5302(6) 0.5053(5) 0.3021(3) 0.0603(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.472(4) . ?
P1 C8 1.872(6) . ?
P1 C22 1.818(6) . ?
P1 C16 1.809(6) . ?
F1 C8 1.420(6) . ?
O1 C7 1.217(7) . ?
C26 H26 0.9300 . ?
C26 C25 1.364(9) . ?
C26 C27 1.392(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.364(10) . ?
C19 C18 1.392(11) . ?
C25 H25 0.9300 . ?
C25 C24 1.373(10) . ?
C8 C9 1.506(8) . ?
C8 C7 1.550(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.394(9) . ?
C10 H10 0.9300 . ?
C10 C9 1.385(8) . ?
C10 C11 1.374(8) . ?
C14 H14 0.9300 . ?
C14 C9 1.380(8) . ?
C14 C13 1.378(10) . ?
C6 H6 0.9300 . ?
C6 C5 1.3900 . ?
C6 C1 1.3900 . ?
C5 H5 0.9300 . ?
C5 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C2 1.3900 . ?
C2 H2 0.9300 . ?
C2 C1 1.3900 . ?
C1 C7 1.490(8) . ?
C12 C13 1.386(10) . ?
C12 C15 1.497(10) . ?
C12 C11 1.392(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(11) . ?
C17 C16 1.387(8) . ?
C13 H13 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C21 H21 0.9300 . ?
C21 C16 1.406(8) . ?
C22 C27 1.390(8) . ?
C22 C23 1.382(8) . ?
C18 H18 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.391(9) . ?
C27 H27 0.9300 . ?
C23 H23 0.9300 . ?
C11 H11 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
O2 P1 C8 113.6(3) . . ?
O2 P1 C22 113.0(3) . . ?
O2 P1 C16 110.3(3) . . ?
C22 P1 C8 104.7(3) . . ?
C16 P1 C8 105.5(3) . . ?
C16 P1 C22 109.3(3) . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.6(6) . . ?
C27 C26 H26 119.7 . . ?
C20 C19 H19 120.1 . . ?
C20 C19 C18 119.7(7) . . ?
C18 C19 H19 120.1 . . ?
C26 C25 H25 120.1 . . ?
C26 C25 C24 119.8(6) . . ?
C24 C25 H25 120.1 . . ?
F1 C8 P1 105.2(4) . . ?
F1 C8 C9 108.6(4) . . ?
F1 C8 C7 108.7(5) . . ?
C9 C8 P1 113.0(4) . . ?
C9 C8 C7 110.2(5) . . ?
C7 C8 P1 110.8(4) . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(7) . . ?
C21 C20 H20 119.8 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C11 C10 C9 120.9(6) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C9 120.5(7) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C1 C6 H6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C6 C1 C7 124.2(4) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 C7 115.8(4) . . ?
C13 C12 C15 121.8(7) . . ?
C13 C12 C11 116.4(6) . . ?
C11 C12 C15 121.8(8) . . ?
C10 C9 C8 120.0(5) . . ?
C14 C9 C8 121.9(6) . . ?
C14 C9 C10 118.2(6) . . ?
C18 C17 H17 119.4 . . ?
C18 C17 C16 121.2(7) . . ?
C16 C17 H17 119.4 . . ?
C14 C13 C12 122.2(7) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
O1 C7 C8 116.5(6) . . ?
O1 C7 C1 121.7(6) . . ?
C1 C7 C8 121.7(5) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C16 120.8(6) . . ?
C16 C21 H21 119.6 . . ?
C27 C22 P1 116.7(5) . . ?
C23 C22 P1 124.4(4) . . ?
C23 C22 C27 119.0(6) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.2(7) . . ?
C17 C18 H18 119.9 . . ?
C25 C24 H24 119.8 . . ?
C25 C24 C23 120.4(7) . . ?
C23 C24 H24 119.8 . . ?
C26 C27 H27 120.0 . . ?
C22 C27 C26 120.0(6) . . ?
C22 C27 H27 120.0 . . ?
C22 C23 C24 120.2(6) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C10 C11 C12 121.8(7) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C17 C16 P1 116.8(5) . . ?
C17 C16 C21 117.7(6) . . ?
C21 C16 P1 125.5(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 C8 C9 C10 -71.0(6) . . . . ?
P1 C8 C9 C14 111.1(6) . . . . ?
P1 C8 C7 O1 33.7(7) . . . . ?
P1 C8 C7 C1 -150.3(4) . . . . ?
P1 C22 C27 C26 -179.8(6) . . . . ?
P1 C22 C23 C24 -177.7(6) . . . . ?
F1 C8 C9 C10 172.6(5) . . . . ?
F1 C8 C9 C14 -5.4(8) . . . . ?
F1 C8 C7 O1 148.9(6) . . . . ?
F1 C8 C7 C1 -35.1(7) . . . . ?
O2 P1 C8 F1 172.7(3) . . . . ?
O2 P1 C8 C9 54.3(5) . . . . ?
O2 P1 C8 C7 -70.0(5) . . . . ?
O2 P1 C22 C27 -7.1(6) . . . . ?
O2 P1 C22 C23 172.4(6) . . . . ?
O2 P1 C16 C17 0.8(6) . . . . ?
O2 P1 C16 C21 177.8(5) . . . . ?
C26 C25 C24 C23 1.6(12) . . . . ?
C19 C20 C21 C16 0.5(9) . . . . ?
C25 C26 C27 C22 -2.1(12) . . . . ?
C25 C24 C23 C22 -3.1(12) . . . . ?
C8 P1 C22 C27 -131.3(5) . . . . ?
C8 P1 C22 C23 48.3(6) . . . . ?
C8 P1 C16 C17 123.8(5) . . . . ?
C8 P1 C16 C21 -59.2(5) . . . . ?
C20 C19 C18 C17 1.6(12) . . . . ?
C20 C21 C16 P1 -176.2(5) . . . . ?
C20 C21 C16 C17 0.7(8) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C1 C7 O1 163.5(5) . . . . ?
C6 C1 C7 C8 -12.3(7) . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C5 C6 C1 C7 -178.6(5) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C3 C2 C1 C7 178.7(4) . . . . ?
C2 C1 C7 O1 -15.2(7) . . . . ?
C2 C1 C7 C8 169.1(4) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C9 C8 C7 O1 -92.2(7) . . . . ?
C9 C8 C7 C1 83.8(6) . . . . ?
C9 C10 C11 C12 -0.3(11) . . . . ?
C9 C14 C13 C12 -0.5(12) . . . . ?
C13 C14 C9 C8 177.2(7) . . . . ?
C13 C14 C9 C10 -0.8(10) . . . . ?
C13 C12 C11 C10 -0.9(11) . . . . ?
C7 C8 C9 C10 53.5(7) . . . . ?
C7 C8 C9 C14 -124.4(6) . . . . ?
C15 C12 C13 C14 -178.0(8) . . . . ?
C15 C12 C11 C10 178.5(7) . . . . ?
C22 P1 C8 F1 -63.5(4) . . . . ?
C22 P1 C8 C9 178.1(4) . . . . ?
C22 P1 C8 C7 53.8(4) . . . . ?
C22 P1 C16 C17 -124.0(5) . . . . ?
C22 P1 C16 C21 53.0(6) . . . . ?
C18 C19 C20 C21 -1.7(11) . . . . ?
C18 C17 C16 P1 176.4(6) . . . . ?
C18 C17 C16 C21 -0.8(9) . . . . ?
C27 C26 C25 C24 1.0(12) . . . . ?
C27 C22 C23 C24 1.9(11) . . . . ?
C23 C22 C27 C26 0.6(10) . . . . ?
C11 C10 C9 C8 -176.8(6) . . . . ?
C11 C10 C9 C14 1.2(10) . . . . ?
C11 C12 C13 C14 1.3(11) . . . . ?
C16 P1 C8 F1 51.8(4) . . . . ?
C16 P1 C8 C9 -66.6(4) . . . . ?
C16 P1 C8 C7 169.1(4) . . . . ?
C16 P1 C22 C27 116.1(5) . . . . ?
C16 P1 C22 C23 -64.4(6) . . . . ?
C16 C17 C18 C19 -0.4(11) . . . . ?

_olex2_date_sample_data_collection 2020-08-16
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.860
_oxdiff_exptl_absorpt_empirical_full_min 0.545
####################################################################### 
# 
# 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_xieshl_0720
_database_code_depnum_ccdc_archive 'CCDC 2034807'
loop_
_audit_author_name
_audit_author_address
'Xie Shaolei' 'Lanzhou University'
_audit_update_record             
;
2020-09-30 deposited with the CCDC.	2020-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-07-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H19 F2 O2 P, C3 H6 O'
_chemical_formula_sum            'C29 H25 F2 O3 P'
_chemical_formula_weight         490.46
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.0306(3)
_cell_length_b                   9.5877(2)
_cell_length_c                   14.0740(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.455(3)
_cell_angle_gamma                90
_cell_volume                     1276.22(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3288
_cell_measurement_temperature    292.31(10)
_cell_measurement_theta_max      69.6870
_cell_measurement_theta_min      10.3570
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    1.318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64348
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6930
_diffrn_reflns_point_group_measured_fraction_full 0.850
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.871
_diffrn_reflns_theta_min         4.675
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.31(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_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  15.00   1.00    1.00    --   54.00 -57.00   0.00   27
  2  ω     37.00  73.00   1.00    1.00    --   54.00 -57.00   0.00   36
  3  ω     51.00  84.00   1.00    1.00    --   54.00 -99.00   0.00   33
  4  ω     56.00 114.00   1.00    1.00    --  108.00-111.00  90.00   58
  5  ω     50.00 106.00   1.00    1.00    --  108.00-111.00   0.00   56
  6  ω     40.00 118.00   1.00    1.00    --  108.00 -50.00 120.00   78
  7  ω     89.00 159.00   1.00    1.00    --  108.00  63.00  60.00   70
  8  ω     88.00 150.00   1.00    1.00    --  108.00  63.00   0.00   62
  9  ω    101.00 160.00   1.00    1.00    --  108.00 111.00 -90.00   59
 10  ω     36.00 128.00   1.00    1.00    --  108.00 -38.00-150.00   92
 11  ω     31.00 117.00   1.00    1.00    --   54.00  77.00 -60.00   86
 12  ω     18.00  52.00   1.00    1.00    --    0.00  57.00-150.00   34
 13  ω    -24.00  35.00   1.00    1.00    --    0.00  38.00-180.00   59
 14  ω    -15.00  82.00   1.00    1.00    --   54.00 -77.00-180.00   97
 15  ω     21.00  56.00   1.00    1.00    --    0.00  57.00  30.00   35
 16  ω     -2.00  24.00   1.00    1.00    --    0.00 -84.00 -10.00   26
 17  ω     17.00  73.00   1.00    1.00    --   54.00 -38.00-180.00   56
 18  ω     42.00  80.00   1.00    1.00    --   54.00  57.00 120.00   38
 19  ω     30.00  67.00   1.00    1.00    --   54.00  38.00 120.00   37
 20  ω     32.00 101.00   1.00    1.00    --   54.00  38.00-180.00   69
 21  ω     38.00  91.00   1.00    1.00    --   54.00  77.00-180.00   53
 22  ω     86.00 111.00   1.00    1.00    --   54.00-125.00-180.00   25
 23  ω     56.00  89.00   1.00    1.00    --  108.00 -63.00-120.00   33
 24  ω     36.00  80.00   1.00    1.00    --  108.00 -25.00 -60.00   44
 25  ω     91.00 116.00   1.00    1.00    --  108.00  50.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0937311000
_diffrn_orient_matrix_UB_12      -0.0084177000
_diffrn_orient_matrix_UB_13      0.0670922000
_diffrn_orient_matrix_UB_21      0.1024684000
_diffrn_orient_matrix_UB_22      0.0979461000
_diffrn_orient_matrix_UB_23      0.0771556000
_diffrn_orient_matrix_UB_31      -0.0851260000
_diffrn_orient_matrix_UB_32      0.1270774000
_diffrn_orient_matrix_UB_33      -0.0550114000
_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         0.588
_reflns_Friedel_fraction_full    0.681
_reflns_Friedel_fraction_max     0.657
_reflns_number_gt                3687
_reflns_number_total             4006
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1293 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(15)
_refine_ls_extinction_coef       0.0077(8)
_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   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.053
_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)+(0.0550P)²+0.0239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0976
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.67506(7) -0.32392(8) -0.30899(5) 0.0381(2) Uani 1 1 d . . . . .
F1 F 0.0677(3) -0.6935(4) -0.2754(2) 0.1044(10) Uani 1 1 d . . . . .
F2 F -0.41844(17) -0.28200(18) -0.31435(12) 0.0423(4) Uani 1 1 d . . . . .
O1 O -0.5180(3) -0.5843(3) -0.22284(19) 0.0582(6) Uani 1 1 d . . . . .
O2 O -0.7546(2) -0.3532(3) -0.23967(16) 0.0546(7) Uani 1 1 d . . . . .
C1 C -0.3006(3) -0.5466(3) -0.2495(2) 0.0404(7) Uani 1 1 d . . . . .
C2 C -0.2894(4) -0.6841(4) -0.2755(3) 0.0566(9) Uani 1 1 d . . . . .
H2 H -0.366322 -0.743707 -0.286841 0.068 Uiso 1 1 calc R U . . .
C3 C -0.1647(4) -0.7337(5) -0.2847(3) 0.0722(12) Uani 1 1 d . . . . .
H3 H -0.157040 -0.825671 -0.303143 0.087 Uiso 1 1 calc R U . . .
C4 C -0.0531(4) -0.6439(5) -0.2659(3) 0.0661(11) Uani 1 1 d . . . . .
C5 C -0.0581(4) -0.5096(4) -0.2388(3) 0.0562(9) Uani 1 1 d . . . . .
H5 H 0.020629 -0.451981 -0.225605 0.067 Uiso 1 1 calc R U . . .
C6 C -0.1841(3) -0.4600(4) -0.2314(2) 0.0455(7) Uani 1 1 d . . . . .
H6 H -0.190507 -0.367219 -0.214088 0.055 Uiso 1 1 calc R U . . .
C7 C -0.4368(3) -0.5009(3) -0.2393(2) 0.0393(7) Uani 1 1 d . . . . .
C8 C -0.4785(3) -0.3474(3) -0.24879(19) 0.0348(6) Uani 1 1 d . . . . .
C9 C -0.4272(3) -0.2753(3) -0.1471(2) 0.0412(7) Uani 1 1 d . . . . .
C10 C -0.4672(4) -0.3264(5) -0.0683(2) 0.0581(9) Uani 1 1 d . . . . .
H10 H -0.523919 -0.405502 -0.077998 0.070 Uiso 1 1 calc R U . . .
C11 C -0.4237(5) -0.2611(6) 0.0242(3) 0.0761(13) Uani 1 1 d . . . . .
H11 H -0.452794 -0.295421 0.075861 0.091 Uiso 1 1 calc R U . . .
C12 C -0.3385(5) -0.1468(6) 0.0407(3) 0.0801(15) Uani 1 1 d . . . . .
H12 H -0.308223 -0.104032 0.103566 0.096 Uiso 1 1 calc R U . . .
C13 C -0.2981(5) -0.0957(6) -0.0357(4) 0.0833(14) Uani 1 1 d . . . . .
H13 H -0.239704 -0.017772 -0.024438 0.100 Uiso 1 1 calc R U . . .
C14 C -0.3431(4) -0.1587(4) -0.1313(3) 0.0595(9) Uani 1 1 d . . . . .
H14 H -0.316244 -0.121867 -0.183352 0.071 Uiso 1 1 calc R U . . .
C15 C -0.6869(3) -0.1436(3) -0.3474(2) 0.0407(7) Uani 1 1 d . . . . .
C16 C -0.6873(4) -0.0437(4) -0.2761(3) 0.0580(10) Uani 1 1 d . . . . .
H16 H -0.682531 -0.071015 -0.211636 0.070 Uiso 1 1 calc R U . . .
C17 C -0.6948(5) 0.0966(4) -0.3009(3) 0.0732(12) Uani 1 1 d . . . . .
H17 H -0.693190 0.163474 -0.252661 0.088 Uiso 1 1 calc R U . . .
C18 C -0.7045(5) 0.1372(4) -0.3964(3) 0.0706(11) Uani 1 1 d . . . . .
H18 H -0.710157 0.231423 -0.412919 0.085 Uiso 1 1 calc R U . . .
C19 C -0.7058(4) 0.0397(4) -0.4672(3) 0.0651(10) Uani 1 1 d . . . . .
H19 H -0.713693 0.067628 -0.532121 0.078 Uiso 1 1 calc R U . . .
C20 C -0.6955(4) -0.1004(4) -0.4428(2) 0.0544(9) Uani 1 1 d . . . . .
H20 H -0.694389 -0.166152 -0.491126 0.065 Uiso 1 1 calc R U . . .
C21 C -0.7280(3) -0.4289(3) -0.4217(2) 0.0428(7) Uani 1 1 d . . . . .
C22 C -0.8653(4) -0.4746(4) -0.4565(3) 0.0608(10) Uani 1 1 d . . . . .
H22 H -0.926182 -0.451684 -0.421516 0.073 Uiso 1 1 calc R U . . .
C23 C -0.9145(5) -0.5546(5) -0.5435(3) 0.0747(12) Uani 1 1 d . . . . .
H23 H -1.008315 -0.583668 -0.567001 0.090 Uiso 1 1 calc R U . . .
C24 C -0.8252(5) -0.5904(4) -0.5943(3) 0.0713(12) Uani 1 1 d . . . . .
H24 H -0.857551 -0.645740 -0.651764 0.086 Uiso 1 1 calc R U . . .
C25 C -0.6884(5) -0.5452(4) -0.5611(3) 0.0673(11) Uani 1 1 d . . . . .
H25 H -0.628204 -0.569113 -0.596400 0.081 Uiso 1 1 calc R U . . .
C26 C -0.6388(4) -0.4645(4) -0.4755(2) 0.0557(9) Uani 1 1 d . . . . .
H26 H -0.545581 -0.433684 -0.453582 0.067 Uiso 1 1 calc R U . . .
O3 O 0.0292(5) -0.6408(7) 0.1562(3) 0.152(2) Uani 1 1 d . . . . .
C27 C -0.0689(5) -0.5984(7) 0.0899(3) 0.0816(14) Uani 1 1 d . . . . .
C28 C -0.0779(9) -0.4513(8) 0.0643(7) 0.169(3) Uani 1 1 d . . . . .
H28A H -0.004638 -0.401356 0.114412 0.254 Uiso 1 1 calc R U . . .
H28B H -0.168489 -0.415809 0.061872 0.254 Uiso 1 1 calc R U . . .
H28C H -0.066586 -0.439383 -0.000309 0.254 Uiso 1 1 calc R U . . .
C29 C -0.1901(9) -0.6847(9) 0.0302(5) 0.150(3) Uani 1 1 d . . . . .
H29A H -0.155891 -0.769303 0.010031 0.225 Uiso 1 1 calc R U . . .
H29B H -0.245118 -0.633899 -0.028567 0.225 Uiso 1 1 calc R U . . .
H29C H -0.248007 -0.706850 0.070415 0.225 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.478(2) . ?
P1 C8 1.883(3) . ?
P1 C15 1.803(3) . ?
P1 C21 1.803(3) . ?
F1 C4 1.349(4) . ?
F2 C8 1.406(3) . ?
O1 C7 1.217(4) . ?
C1 C2 1.382(5) . ?
C1 C6 1.387(5) . ?
C1 C7 1.487(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(6) . ?
C4 C5 1.349(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.524(4) . ?
C8 C9 1.517(4) . ?
C9 C10 1.389(5) . ?
C9 C14 1.373(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.361(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.360(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.406(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(5) . ?
C15 C20 1.381(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.362(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(5) . ?
C21 C26 1.394(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.388(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.364(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.364(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.378(5) . ?
C26 H26 0.9300 . ?
O3 C27 1.180(5) . ?
C27 C28 1.451(9) . ?
C27 C29 1.479(8) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 C8 113.27(12) . . ?
O2 P1 C15 112.53(14) . . ?
O2 P1 C21 114.14(15) . . ?
C15 P1 C8 101.78(13) . . ?
C21 P1 C8 106.65(14) . . ?
C21 P1 C15 107.53(14) . . ?
C2 C1 C6 118.8(3) . . ?
C2 C1 C7 117.7(3) . . ?
C6 C1 C7 123.5(3) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.5(4) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3 120.9 . . ?
F1 C4 C3 117.6(4) . . ?
C5 C4 F1 118.9(4) . . ?
C5 C4 C3 123.5(3) . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.0(4) . . ?
C6 C5 H5 121.0 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
O1 C7 C1 121.3(3) . . ?
O1 C7 C8 118.0(3) . . ?
C1 C7 C8 120.7(3) . . ?
F2 C8 P1 105.35(17) . . ?
F2 C8 C7 108.9(2) . . ?
F2 C8 C9 109.3(2) . . ?
C7 C8 P1 111.8(2) . . ?
C9 C8 P1 110.21(18) . . ?
C9 C8 C7 111.1(2) . . ?
C10 C9 C8 119.7(3) . . ?
C14 C9 C8 121.4(3) . . ?
C14 C9 C10 118.9(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.1(4) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 C13 119.3(4) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 P1 117.4(3) . . ?
C20 C15 P1 123.8(3) . . ?
C20 C15 C16 118.8(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.6(3) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 P1 117.4(3) . . ?
C22 C21 C26 118.5(3) . . ?
C26 C21 P1 124.1(3) . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.8(4) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 119.9(4) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.1(4) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.5(4) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 H26 119.9 . . ?
C25 C26 C21 120.2(4) . . ?
C25 C26 H26 119.9 . . ?
O3 C27 C28 119.8(7) . . ?
O3 C27 C29 124.6(7) . . ?
C28 C27 C29 115.6(5) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C8 C9 C10 67.8(3) . . . . ?
P1 C8 C9 C14 -111.2(3) . . . . ?
P1 C15 C16 C17 179.3(3) . . . . ?
P1 C15 C20 C19 179.3(3) . . . . ?
P1 C21 C22 C23 179.2(3) . . . . ?
P1 C21 C26 C25 -179.9(3) . . . . ?
F1 C4 C5 C6 178.8(3) . . . . ?
F2 C8 C9 C10 -176.8(3) . . . . ?
F2 C8 C9 C14 4.1(4) . . . . ?
O1 C7 C8 P1 -34.3(3) . . . . ?
O1 C7 C8 F2 -150.3(3) . . . . ?
O1 C7 C8 C9 89.2(3) . . . . ?
O2 P1 C8 F2 -165.13(17) . . . . ?
O2 P1 C8 C7 76.8(2) . . . . ?
O2 P1 C8 C9 -47.3(2) . . . . ?
O2 P1 C15 C16 37.0(3) . . . . ?
O2 P1 C15 C20 -143.0(3) . . . . ?
O2 P1 C21 C22 28.7(3) . . . . ?
O2 P1 C21 C26 -152.2(3) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C1 C7 C8 P1 145.9(2) . . . . ?
C1 C7 C8 F2 29.9(3) . . . . ?
C1 C7 C8 C9 -90.6(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C2 C1 C7 O1 22.5(4) . . . . ?
C2 C1 C7 C8 -157.7(3) . . . . ?
C2 C3 C4 F1 -179.8(4) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C6 C1 C2 C3 -0.9(5) . . . . ?
C6 C1 C7 O1 -155.5(3) . . . . ?
C6 C1 C7 C8 24.3(4) . . . . ?
C7 C1 C2 C3 -179.0(3) . . . . ?
C7 C1 C6 C5 177.8(3) . . . . ?
C7 C8 C9 C10 -56.6(4) . . . . ?
C7 C8 C9 C14 124.3(3) . . . . ?
C8 P1 C15 C16 -84.6(3) . . . . ?
C8 P1 C15 C20 95.4(3) . . . . ?
C8 P1 C21 C22 154.5(3) . . . . ?
C8 P1 C21 C26 -26.3(3) . . . . ?
C8 C9 C10 C11 -178.9(3) . . . . ?
C8 C9 C14 C13 -179.9(3) . . . . ?
C9 C10 C11 C12 -1.2(6) . . . . ?
C10 C9 C14 C13 1.0(5) . . . . ?
C10 C11 C12 C13 1.0(7) . . . . ?
C11 C12 C13 C14 0.2(7) . . . . ?
C12 C13 C14 C9 -1.2(6) . . . . ?
C14 C9 C10 C11 0.2(5) . . . . ?
C15 P1 C8 F2 -44.1(2) . . . . ?
C15 P1 C8 C7 -162.17(19) . . . . ?
C15 P1 C8 C9 73.8(2) . . . . ?
C15 P1 C21 C22 -96.9(3) . . . . ?
C15 P1 C21 C26 82.2(3) . . . . ?
C15 C16 C17 C18 1.2(7) . . . . ?
C16 C15 C20 C19 -0.7(5) . . . . ?
C16 C17 C18 C19 -0.5(7) . . . . ?
C17 C18 C19 C20 -0.9(7) . . . . ?
C18 C19 C20 C15 1.4(6) . . . . ?
C20 C15 C16 C17 -0.6(6) . . . . ?
C21 P1 C8 F2 68.5(2) . . . . ?
C21 P1 C8 C7 -49.6(2) . . . . ?
C21 P1 C8 C9 -173.7(2) . . . . ?
C21 P1 C15 C16 163.5(3) . . . . ?
C21 P1 C15 C20 -16.5(3) . . . . ?
C21 C22 C23 C24 1.0(6) . . . . ?
C22 C21 C26 C25 -0.8(6) . . . . ?
C22 C23 C24 C25 -1.4(7) . . . . ?
C23 C24 C25 C26 0.7(7) . . . . ?
C24 C25 C26 C21 0.4(6) . . . . ?
C26 C21 C22 C23 0.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.631
_oxdiff_exptl_absorpt_empirical_full_min 0.617
####################################################################### 
# 
# 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_xieshl_190_392_2
_database_code_depnum_ccdc_archive 'CCDC 2034799'
loop_
_audit_author_name
_audit_author_address
'Xie Shaolei' 'Lanzhou University'
_audit_update_record             
;
2020-09-30 deposited with the CCDC.	2020-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-08-19
_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         'C18 H18 F O2 P'
_chemical_formula_sum            'C18 H18 F O2 P'
_chemical_formula_weight         316.29
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0210(6)
_cell_length_b                   9.7257(8)
_cell_length_c                   11.0936(8)
_cell_angle_alpha                81.880(6)
_cell_angle_beta                 81.526(6)
_cell_angle_gamma                66.712(8)
_cell_volume                     782.94(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4044
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8520
_cell_measurement_theta_min      4.9220
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.836
_exptl_absorpt_coefficient_mu    1.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32615
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7365
_diffrn_reflns_point_group_measured_fraction_full 0.768
_diffrn_reflns_point_group_measured_fraction_max 0.768
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         4.046
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00  78.00   1.00    2.00    --   54.00 -77.00  90.00   48
  2  ω     48.00  91.00   1.00    2.00    --   54.00 -23.00  42.00   43
  3  ω     78.00 146.00   1.00    4.00    --  108.00 -91.00  90.00   68
  4  ω     62.00 115.00   1.00    4.00    --  108.00-111.00 -90.00   53
  5  ω     93.00 145.00   1.00    4.00    --  108.00 -91.00 -90.00   52
  6  ω    104.00 176.00   1.00    4.00    --  108.00  38.00-150.00   72
  7  ω    100.00 149.00   1.00    4.00    --  108.00 111.00 -30.00   49
  8  ω     96.00 159.00   1.00    4.00    --  108.00  38.00 -30.00   63
  9  ω     94.00 122.00   1.00    2.00    --   54.00  57.00-120.00   28
 10  ω     79.00 164.00   1.00    4.00    --  108.00  77.00 -90.00   85
 11  ω     86.00 177.00   1.00    4.00    --  108.00  50.00-120.00   91
 12  ω     55.00 126.00   1.00    4.00    --  108.00 -38.00 -90.00   71
 13  ω     51.00 128.00   1.00    4.00    --  108.00 -50.00  60.00   77
 14  ω     37.00 103.00   1.00    4.00    --  108.00-111.00  90.00   66
 15  ω     36.00  63.00   1.00    4.00    --  108.00 -91.00  90.00   27
 16  ω     -2.00  45.00   1.00    2.00    --   54.00 -23.00  42.00   47
 17  ω    -13.00  22.00   1.00    1.00    --    0.00  57.00  30.00   35
 18  ω    -13.00  37.00   1.00    2.00    --   54.00 -57.00 -90.00   50
 19  ω      7.00  80.00   1.00    2.00    --   54.00 -99.00 -90.00   73
 20  ω     43.00 125.00   1.00    4.00    --  108.00 -63.00-150.00   82
 21  ω     38.00 123.00   1.00    2.00    --   54.00  57.00-150.00   85
 22  ω     42.00  69.00   1.00    1.00    --    0.00  57.00  30.00   27
 23  ω    -19.00  20.00   1.00    1.00    --    0.00 -57.00-120.00   39
 24  ω    -16.00  81.00   1.00    2.00    --   54.00 -77.00   0.00   97
 25  ω    -63.00 -37.00   1.00    1.00    --    0.00 -57.00-120.00   26
 26  ω     19.00  45.00   1.00    1.00    --    0.00  57.00-120.00   26
 27  ω    -25.00   7.00   1.00    1.00    --    0.00  19.00-180.00   32
 28  ω     34.00  60.00   1.00    1.00    --    0.00  19.00-180.00   26
 29  ω    -17.00   9.00   1.00    1.00    --    0.00  57.00-120.00   26
 30  ω    -18.00   9.00   1.00    1.00    --   24.00 106.00 179.94   27
 31  ω     -2.00  23.00   1.00    2.00    --   36.00  92.00   8.71   25
 32  ω     -6.00  19.00   1.00    2.00    --   36.00  99.00 -95.83   25
 33  ω      2.00  27.00   1.00    2.00    --   40.00  92.00-173.00   25
 34  ω     12.00  37.00   1.00    2.00    --   44.00  81.00 117.43   25
 35  ω     16.00  41.00   1.00    2.00    --   48.00  80.00   0.36   25
 36  ω     20.00  45.00   1.00    2.00    --   52.00  80.00 102.29   25
 37  ω     21.00  46.00   1.00    2.00    --   52.00  79.00 156.41   25
 38  ω     90.00 116.00   1.00    2.00    --   54.00  77.00  60.00   26
 39  ω     24.00  67.00   1.00    2.00    --   54.00  77.00  60.00   43
 40  ω     25.00  51.00   1.00    2.00    --   54.00  77.00 -60.00   26
 41  ω     26.00  52.00   1.00    2.00    --   54.00  77.00-120.00   26
 42  ω     42.00  73.00   1.00    2.00    --   54.00 -57.00 120.00   31
 43  ω     30.00  62.00   1.00    2.00    --   56.00  75.00-154.85   32
 44  ω     99.00 125.00   1.00    2.00    --   60.00  57.00 117.55   26
 45  ω    104.00 129.00   1.00    2.00    --   60.00  71.00 -27.26   25
 46  ω     34.00  72.00   1.00    2.00    --   60.00  71.00 -27.26   38
 47  ω     40.00  65.00   1.00    2.00    --   60.00  57.00 117.55   25
 48  ω     34.00  60.00   1.00    2.00    --   60.00  70.00 -96.81   26
 49  ω     40.00  74.00   1.00    2.00    --   64.00  71.00  19.87   34
 50  ω     78.00 127.00   1.00    2.00    --   64.00  71.00  19.87   49
 51  ω     42.00  69.00   1.00    2.00    --   64.00  62.00 122.77   27
 52  ω     48.00  79.00   1.00    2.00    --   68.00  61.00 -49.85   31
 53  ω     48.00  87.00   1.00    2.00    --   68.00  53.00-160.59   39
 54  ω     45.00  71.00   1.00    2.00    --   68.00  47.00  38.82   26
 55  ω     41.00  71.00   1.00    2.00    --   68.00  74.00 130.68   30
 56  ω     50.00  76.00   1.00    2.00    --   72.00  66.00 -99.44   26
 57  ω     55.00 100.00   1.00    2.00    --   76.00  62.00 160.70   45
 58  ω     59.00  89.00   1.00    2.00    --   80.00  46.00 145.00   30
 59  ω     78.00 104.00   1.00    4.00    --  108.00  77.00 -30.00   26
 60  ω     83.00 110.00   1.00    4.00    --  108.00  38.00  30.00   27
 61  ω     79.00 105.00   1.00    4.00    --  108.00  77.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1729671000
_diffrn_orient_matrix_UB_12      0.0363687000
_diffrn_orient_matrix_UB_13      -0.0219499000
_diffrn_orient_matrix_UB_21      0.1169857000
_diffrn_orient_matrix_UB_22      -0.1662954000
_diffrn_orient_matrix_UB_23      0.0344374000
_diffrn_orient_matrix_UB_31      0.0238178000
_diffrn_orient_matrix_UB_32      -0.0318253000
_diffrn_orient_matrix_UB_33      -0.1349472000
_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         0.542
_reflns_Friedel_fraction_full    0.540
_reflns_Friedel_fraction_max     0.540
_reflns_number_gt                3984
_reflns_number_total             4258
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 1286 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.061
_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)+(0.1069P)²+0.4491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1694
_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 Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C4(H4A,H4B), C23(H23A,H23B), C21(H21A,
 H21B), C22(H22A,H22B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C18(H18), C17(H17),
 C16(H16), C15(H15), C26(H26), C27(H27), C29(H29), C28(H28), C30(H30), C32(H32),
  C33(H33), C34(H34), C35(H35), C36(H36)
2.c Fitted hexagon refined as free rotating group:
 C7(C8,C9,C10,C11,C12), C13(C18,C17,C16,C15,C14), C25(C26,C27,C29,C28,C30),
 C32(C33,C34,C35,C36,C31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.23909(17) 0.70216(14) 0.50654(12) 0.0383(4) Uani 1 1 d . . . . .
F1 F 0.0346(6) 0.6848(5) 0.7100(4) 0.0628(13) Uani 1 1 d . . . . .
O1 O -0.0020(8) 0.4630(6) 0.6309(6) 0.0809(15) Uani 1 1 d . . . . .
O2 O 0.2424(7) 0.7181(6) 0.3724(4) 0.0505(13) Uani 1 1 d . . . . .
C7 C 0.4113(5) 0.5257(4) 0.5608(4) 0.0417(17) Uani 1 1 d G . . . .
C8 C 0.4303(7) 0.4710(5) 0.6828(3) 0.053(2) Uani 1 1 d G . . . .
H8 H 0.345245 0.522370 0.743961 0.063 Uiso 1 1 calc R U . . .
C9 C 0.5763(8) 0.3396(6) 0.7134(4) 0.0554(19) Uani 1 1 d G . . . .
H9 H 0.588938 0.302982 0.795101 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7033(6) 0.2628(5) 0.6220(5) 0.059(2) Uani 1 1 d G . . . .
H10 H 0.801013 0.174818 0.642549 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6844(6) 0.3174(5) 0.5000(5) 0.059(2) Uani 1 1 d G . . . .
H11 H 0.769396 0.266039 0.438855 0.071 Uiso 1 1 calc R U . . .
C12 C 0.5384(7) 0.4489(5) 0.4694(3) 0.0470(18) Uani 1 1 d G . . . .
H12 H 0.525704 0.485428 0.387712 0.056 Uiso 1 1 calc R U . . .
C3 C -0.0698(12) 0.5785(10) 0.4300(9) 0.064(2) Uani 1 1 d . . . . .
H3A H -0.096890 0.492031 0.420779 0.077 Uiso 1 1 calc R U . . .
H3B H 0.029771 0.579976 0.369150 0.077 Uiso 1 1 calc R U . . .
C13 C 0.2125(7) 0.9900(5) 0.4867(4) 0.053(2) Uani 1 1 d G . . . .
H13 H 0.168067 0.994829 0.412711 0.063 Uiso 1 1 calc R U . . .
C18 C 0.2277(9) 1.1162(4) 0.5213(5) 0.071(3) Uani 1 1 d G . . . .
H18 H 0.193506 1.205348 0.470410 0.085 Uiso 1 1 calc R U . . .
C17 C 0.2941(10) 1.1090(5) 0.6318(6) 0.065(2) Uani 1 1 d G . . . .
H17 H 0.304278 1.193424 0.654968 0.078 Uiso 1 1 calc R U . . .
C16 C 0.3452(9) 0.9758(6) 0.7078(5) 0.066(3) Uani 1 1 d G . . . .
H16 H 0.389611 0.970981 0.781827 0.079 Uiso 1 1 calc R U . . .
C15 C 0.3300(8) 0.8496(5) 0.6733(4) 0.057(2) Uani 1 1 d G . . . .
H15 H 0.364173 0.760461 0.724131 0.069 Uiso 1 1 calc R U . . .
C14 C 0.2636(7) 0.8568(4) 0.5627(4) 0.0386(16) Uani 1 1 d G . . . .
C1 C 0.0160(10) 0.7002(8) 0.5863(7) 0.0453(18) Uani 1 1 d . . . . .
C5 C -0.2095(14) 0.8632(11) 0.4326(10) 0.074(3) Uani 1 1 d . . . . .
H5A H -0.118614 0.879601 0.370810 0.089 Uiso 1 1 calc R U . . .
H5B H -0.322926 0.950097 0.426077 0.089 Uiso 1 1 calc R U . . .
C6 C -0.1475(10) 0.8463(8) 0.5588(8) 0.057(2) Uani 1 1 d . . . . .
H6A H -0.248821 0.850260 0.619860 0.068 Uiso 1 1 calc R U . . .
H6B H -0.115594 0.930793 0.566295 0.068 Uiso 1 1 calc R U . . .
C2 C -0.0151(10) 0.5663(8) 0.5545(8) 0.0479(18) Uani 1 1 d . . . . .
C4 C -0.2377(13) 0.7221(12) 0.4100(10) 0.072(3) Uani 1 1 d . . . . .
H4A H -0.340371 0.714376 0.464628 0.087 Uiso 1 1 calc R U . . .
H4B H -0.267182 0.732180 0.326664 0.087 Uiso 1 1 calc R U . . .
P2 P 0.03874(18) 0.24377(14) 0.10579(12) 0.0388(4) Uani 1 1 d . . . . .
F2 F 0.2356(6) 0.2789(6) -0.0967(4) 0.0644(13) Uani 1 1 d . . . . .
O4 O 0.4893(7) 0.0298(6) -0.0297(6) 0.0768(15) Uani 1 1 d . . . . .
O3 O 0.0372(7) 0.2255(5) 0.2417(4) 0.0483(13) Uani 1 1 d . . . . .
C23 C 0.3479(13) 0.3590(10) 0.1942(9) 0.063(2) Uani 1 1 d . . . . .
H23A H 0.250516 0.348844 0.253249 0.075 Uiso 1 1 calc R U . . .
H23B H 0.371301 0.443894 0.212618 0.075 Uiso 1 1 calc R U . . .
C25 C -0.1387(5) 0.4152(4) 0.0517(4) 0.0382(16) Uani 1 1 d G . . . .
C26 C -0.1604(7) 0.4675(6) -0.0705(4) 0.055(2) Uani 1 1 d G . . . .
H26 H -0.076673 0.415097 -0.131691 0.066 Uiso 1 1 calc R U . . .
C27 C -0.3073(9) 0.5982(6) -0.1012(4) 0.070(2) Uani 1 1 d G . . . .
H27 H -0.321848 0.633252 -0.182986 0.083 Uiso 1 1 calc R U . . .
C29 C -0.4325(7) 0.6766(5) -0.0097(6) 0.068(3) Uani 1 1 d G . . . .
H29 H -0.530790 0.764051 -0.030302 0.082 Uiso 1 1 calc R U . . .
C28 C -0.4108(7) 0.6243(6) 0.1125(5) 0.062(2) Uani 1 1 d G . . . .
H28 H -0.494559 0.676695 0.173678 0.074 Uiso 1 1 calc R U . . .
C30 C -0.2639(7) 0.4936(5) 0.1432(4) 0.0513(19) Uani 1 1 d G . . . .
H30 H -0.249385 0.458539 0.224975 0.062 Uiso 1 1 calc R U . . .
C21 C 0.4867(12) 0.0851(8) 0.1747(8) 0.060(2) Uani 1 1 d . . . . .
H21A H 0.600304 -0.002385 0.175027 0.072 Uiso 1 1 calc R U . . .
H21B H 0.399181 0.063374 0.236449 0.072 Uiso 1 1 calc R U . . .
C32 C 0.0730(7) -0.0489(5) 0.1248(4) 0.054(2) Uani 1 1 d G . . . .
H32 H 0.118404 -0.053806 0.198411 0.064 Uiso 1 1 calc R U . . .
C33 C 0.0557(9) -0.1746(4) 0.0911(5) 0.064(2) Uani 1 1 d G . . . .
H33 H 0.089555 -0.263597 0.142121 0.077 Uiso 1 1 calc R U . . .
C34 C -0.0122(10) -0.1672(5) -0.0189(5) 0.067(3) Uani 1 1 d G . . . .
H34 H -0.023797 -0.251327 -0.041514 0.080 Uiso 1 1 calc R U . . .
C35 C -0.0629(10) -0.0342(6) -0.0952(5) 0.071(3) Uani 1 1 d G . . . .
H35 H -0.108301 -0.029265 -0.168860 0.085 Uiso 1 1 calc R U . . .
C36 C -0.0456(9) 0.0915(5) -0.0615(5) 0.062(2) Uani 1 1 d G . . . .
H36 H -0.079453 0.180528 -0.112573 0.074 Uiso 1 1 calc R U . . .
C31 C 0.0223(8) 0.0842(4) 0.0485(5) 0.0447(18) Uani 1 1 d G . . . .
C22 C 0.5184(14) 0.2178(11) 0.2073(11) 0.079(3) Uani 1 1 d . . . . .
H22A H 0.619383 0.230398 0.153772 0.094 Uiso 1 1 calc R U . . .
H22B H 0.549549 0.199970 0.290922 0.094 Uiso 1 1 calc R U . . .
C19 C 0.2537(11) 0.2581(9) 0.0301(7) 0.0447(17) Uani 1 1 d . . . . .
C24 C 0.2866(14) 0.3899(9) 0.0677(9) 0.061(2) Uani 1 1 d . . . . .
H24A H 0.378863 0.409992 0.009408 0.074 Uiso 1 1 calc R U . . .
H24B H 0.174902 0.478916 0.065129 0.074 Uiso 1 1 calc R U . . .
C20 C 0.4176(11) 0.1128(9) 0.0524(7) 0.053(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.472(5) . ?
P1 C7 1.815(4) . ?
P1 C14 1.795(4) . ?
P1 C1 1.882(8) . ?
F1 C1 1.383(8) . ?
O1 C2 1.201(9) . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?
C10 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 C12 1.3900 . ?
C12 H12 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.485(11) . ?
C3 C4 1.525(13) . ?
C13 H13 0.9300 . ?
C13 C18 1.3900 . ?
C13 C14 1.3900 . ?
C18 H18 0.9300 . ?
C18 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C16 1.3900 . ?
C16 H16 0.9300 . ?
C16 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C1 C6 1.535(10) . ?
C1 C2 1.515(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.519(12) . ?
C5 C4 1.535(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
P2 O3 1.491(5) . ?
P2 C25 1.805(4) . ?
P2 C31 1.815(4) . ?
P2 C19 1.851(8) . ?
F2 C19 1.413(8) . ?
O4 C20 1.224(9) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C22 1.514(13) . ?
C23 C24 1.506(12) . ?
C25 C26 1.3900 . ?
C25 C30 1.3900 . ?
C26 H26 0.9300 . ?
C26 C27 1.3900 . ?
C27 H27 0.9300 . ?
C27 C29 1.3900 . ?
C29 H29 0.9300 . ?
C29 C28 1.3900 . ?
C28 H28 0.9300 . ?
C28 C30 1.3900 . ?
C30 H30 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.510(12) . ?
C21 C20 1.491(10) . ?
C32 H32 0.9300 . ?
C32 C33 1.3900 . ?
C32 C31 1.3900 . ?
C33 H33 0.9300 . ?
C33 C34 1.3900 . ?
C34 H34 0.9300 . ?
C34 C35 1.3900 . ?
C35 H35 0.9300 . ?
C35 C36 1.3900 . ?
C36 H36 0.9300 . ?
C36 C31 1.3900 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C19 C24 1.529(11) . ?
C19 C20 1.522(11) . ?
C24 H24A 0.9700 . ?
C24 H24B 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
O2 P1 C7 111.6(3) . . ?
O2 P1 C14 112.4(3) . . ?
O2 P1 C1 112.4(3) . . ?
C7 P1 C1 105.2(3) . . ?
C14 P1 C7 110.2(2) . . ?
C14 P1 C1 104.5(3) . . ?
C8 C7 P1 125.3(3) . . ?
C8 C7 C12 120.0 . . ?
C12 C7 P1 114.5(3) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 H12 120.0 . . ?
H3A C3 H3B 108.2 . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C2 C3 C4 109.9(7) . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C18 C13 H13 120.0 . . ?
C18 C13 C14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C18 H18 120.0 . . ?
C13 C18 C17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C13 C14 P1 115.5(3) . . ?
C15 C14 P1 124.5(3) . . ?
C15 C14 C13 120.0 . . ?
F1 C1 P1 105.4(5) . . ?
F1 C1 C6 108.0(6) . . ?
F1 C1 C2 109.3(6) . . ?
C6 C1 P1 113.3(6) . . ?
C2 C1 P1 110.1(5) . . ?
C2 C1 C6 110.5(6) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 C4 110.6(7) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C1 C6 H6A 108.7 . . ?
C1 C6 H6B 108.7 . . ?
C5 C6 C1 114.2(7) . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
O1 C2 C3 125.0(7) . . ?
O1 C2 C1 119.1(7) . . ?
C3 C2 C1 115.8(7) . . ?
C3 C4 C5 112.6(7) . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
O3 P2 C25 112.6(3) . . ?
O3 P2 C31 111.8(3) . . ?
O3 P2 C19 111.2(3) . . ?
C25 P2 C31 109.7(2) . . ?
C25 P2 C19 104.7(3) . . ?
C31 P2 C19 106.4(3) . . ?
H23A C23 H23B 107.8 . . ?
C22 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
C24 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C24 C23 C22 112.6(8) . . ?
C26 C25 P2 125.2(3) . . ?
C26 C25 C30 120.0 . . ?
C30 C25 P2 114.8(3) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C27 C26 120.0 . . ?
C29 C27 H27 120.0 . . ?
C27 C29 H29 120.0 . . ?
C27 C29 C28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C28 H28 120.0 . . ?
C29 C28 C30 120.0 . . ?
C30 C28 H28 120.0 . . ?
C25 C30 H30 120.0 . . ?
C28 C30 C25 120.0 . . ?
C28 C30 H30 120.0 . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
C20 C21 C22 112.3(7) . . ?
C33 C32 H32 120.0 . . ?
C33 C32 C31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 120.0 . . ?
C31 C36 C35 120.0 . . ?
C31 C36 H36 120.0 . . ?
C32 C31 P2 116.1(3) . . ?
C36 C31 P2 123.8(3) . . ?
C36 C31 C32 120.0 . . ?
C23 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C21 C22 C23 109.9(7) . . ?
C21 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
F2 C19 P2 105.5(5) . . ?
F2 C19 C24 109.6(6) . . ?
F2 C19 C20 107.0(6) . . ?
C24 C19 P2 112.9(6) . . ?
C20 C19 P2 111.8(5) . . ?
C20 C19 C24 109.9(6) . . ?
C23 C24 C19 112.1(7) . . ?
C23 C24 H24A 109.2 . . ?
C23 C24 H24B 109.2 . . ?
C19 C24 H24A 109.2 . . ?
C19 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
O4 C20 C21 123.9(8) . . ?
O4 C20 C19 119.9(7) . . ?
C21 C20 C19 116.1(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C7 C8 C9 -175.1(4) . . . . ?
P1 C7 C12 C11 175.6(4) . . . . ?
P1 C1 C6 C5 75.5(8) . . . . ?
P1 C1 C2 O1 108.1(8) . . . . ?
P1 C1 C2 C3 -75.0(7) . . . . ?
F1 C1 C6 C5 -168.2(7) . . . . ?
F1 C1 C2 O1 -7.2(9) . . . . ?
F1 C1 C2 C3 169.7(6) . . . . ?
O2 P1 C7 C8 -173.0(3) . . . . ?
O2 P1 C7 C12 11.6(4) . . . . ?
O2 P1 C14 C13 23.8(4) . . . . ?
O2 P1 C14 C15 -155.7(4) . . . . ?
O2 P1 C1 F1 -180.0(4) . . . . ?
O2 P1 C1 C6 -62.1(6) . . . . ?
O2 P1 C1 C2 62.2(6) . . . . ?
C7 P1 C14 C13 148.9(3) . . . . ?
C7 P1 C14 C15 -30.5(4) . . . . ?
C7 P1 C1 F1 58.3(5) . . . . ?
C7 P1 C1 C6 176.2(5) . . . . ?
C7 P1 C1 C2 -59.5(5) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
C13 C18 C17 C16 0.0 . . . . ?
C18 C13 C14 P1 -179.4(4) . . . . ?
C18 C13 C14 C15 0.0 . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
C17 C16 C15 C14 0.0 . . . . ?
C16 C15 C14 P1 179.4(4) . . . . ?
C16 C15 C14 C13 0.0 . . . . ?
C14 P1 C7 C8 61.4(4) . . . . ?
C14 P1 C7 C12 -114.0(3) . . . . ?
C14 P1 C1 F1 -57.8(5) . . . . ?
C14 P1 C1 C6 60.0(6) . . . . ?
C14 P1 C1 C2 -175.6(5) . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C1 P1 C7 C8 -50.8(4) . . . . ?
C1 P1 C7 C12 133.9(3) . . . . ?
C1 P1 C14 C13 -98.5(4) . . . . ?
C1 P1 C14 C15 82.1(4) . . . . ?
C6 C1 C2 O1 -125.9(8) . . . . ?
C6 C1 C2 C3 51.0(9) . . . . ?
C6 C5 C4 C3 -54.0(11) . . . . ?
C2 C3 C4 C5 55.0(11) . . . . ?
C2 C1 C6 C5 -48.6(9) . . . . ?
C4 C3 C2 O1 122.4(9) . . . . ?
C4 C3 C2 C1 -54.3(9) . . . . ?
C4 C5 C6 C1 51.0(10) . . . . ?
P2 C25 C26 C27 177.2(4) . . . . ?
P2 C25 C30 C28 -177.5(4) . . . . ?
P2 C19 C24 C23 75.4(8) . . . . ?
P2 C19 C20 O4 105.3(8) . . . . ?
P2 C19 C20 C21 -77.7(7) . . . . ?
F2 C19 C24 C23 -167.4(7) . . . . ?
F2 C19 C20 O4 -9.6(9) . . . . ?
F2 C19 C20 C21 167.3(6) . . . . ?
O3 P2 C25 C26 174.4(3) . . . . ?
O3 P2 C25 C30 -8.2(4) . . . . ?
O3 P2 C31 C32 -21.3(4) . . . . ?
O3 P2 C31 C36 155.2(4) . . . . ?
O3 P2 C19 F2 -178.5(4) . . . . ?
O3 P2 C19 C24 -58.8(7) . . . . ?
O3 P2 C19 C20 65.7(6) . . . . ?
C25 P2 C31 C32 -147.0(3) . . . . ?
C25 P2 C31 C36 29.5(4) . . . . ?
C25 P2 C19 F2 -56.6(5) . . . . ?
C25 P2 C19 C24 63.0(6) . . . . ?
C25 P2 C19 C20 -172.5(5) . . . . ?
C25 C26 C27 C29 0.0 . . . . ?
C26 C25 C30 C28 0.0 . . . . ?
C26 C27 C29 C28 0.0 . . . . ?
C27 C29 C28 C30 0.0 . . . . ?
C29 C28 C30 C25 0.0 . . . . ?
C30 C25 C26 C27 0.0 . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C33 C32 C31 P2 176.7(4) . . . . ?
C33 C32 C31 C36 0.0 . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C31 0.0 . . . . ?
C35 C36 C31 P2 -176.4(5) . . . . ?
C35 C36 C31 C32 0.0 . . . . ?
C31 P2 C25 C26 -60.4(4) . . . . ?
C31 P2 C25 C30 117.0(3) . . . . ?
C31 P2 C19 F2 59.6(5) . . . . ?
C31 P2 C19 C24 179.2(5) . . . . ?
C31 P2 C19 C20 -56.3(6) . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C22 C23 C24 C19 56.7(10) . . . . ?
C22 C21 C20 O4 125.9(9) . . . . ?
C22 C21 C20 C19 -50.9(10) . . . . ?
C19 P2 C25 C26 53.4(4) . . . . ?
C19 P2 C25 C30 -129.2(3) . . . . ?
C19 P2 C31 C32 100.3(4) . . . . ?
C19 P2 C31 C36 -83.2(4) . . . . ?
C24 C23 C22 C21 -56.8(11) . . . . ?
C24 C19 C20 O4 -128.5(8) . . . . ?
C24 C19 C20 C21 48.4(9) . . . . ?
C20 C21 C22 C23 52.8(12) . . . . ?
C20 C19 C24 C23 -50.1(9) . . . . ?

_olex2_date_sample_data_collection 2020-08-16
_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 3.014
_oxdiff_exptl_absorpt_empirical_full_min 0.477
