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

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

data_yimingj_0702_auto
_database_code_depnum_ccdc_archive 'CCDC 2112791'
loop_
_audit_author_name
_audit_author_address
'Mingjun Yi' 'Lanzhou university'
_audit_update_record             
;
2021-09-29 deposited with the CCDC.	2021-11-15 downloaded from the CCDC.
;
_audit_creation_date             2021-07-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 F3 N O P'
_chemical_formula_sum            'C23 H21 F3 N O P'
_chemical_formula_weight         415.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.80270(10)
_cell_length_b                   20.2100(2)
_cell_length_c                   11.48090(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.0740(10)
_cell_angle_gamma                90
_cell_volume                     1989.54(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9770
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.1570
_cell_measurement_theta_min      4.5120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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    1.387
_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  0.0299
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13733
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.137
_diffrn_reflns_theta_min         4.375
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     70.00 118.00   0.50    0.05    --   46.32  55.00  65.00   96
  2  ω    149.00 174.00   0.50    0.05    --  104.25  61.00 -30.00   50
  3  ω     92.00 175.00   0.50    0.05    --  104.25  45.00   0.00  166
  4  ω     93.00 118.00   0.50    0.05    --  104.25  61.00 -30.00   50
  5  ω     97.00 154.00   0.50    0.05    --  104.25  55.00  65.00  114
  6  ω    121.00 147.00   0.50    0.05    --  104.25 125.00 120.00   52
  7  ω     84.00 117.00   0.50    0.05    --  104.25 125.00 120.00   66
  8  ω     50.00 101.00   0.50    0.05    --  104.25 -77.00-180.00  102
  9  ω     37.00  64.00   0.50    0.05    --  104.25 -61.00-180.00   54
 10  ω     46.00  72.00   0.50    0.05    --  104.25 -61.00-120.00   52
 11  ω     32.00  64.00   0.50    0.05    --  104.25 -55.00 -78.00   64
 12  ω    -25.00  61.00   0.50    0.05    --   46.32 -55.00 -78.00  172
 13  ω    -49.00  26.00   0.50    0.05    --  -46.32  55.00  65.00  150
 14  ω    -64.00 -29.00   0.50    0.05    -- -102.00  61.00 120.00   70
 15  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -60.00   80
 16  ω    -66.00 -31.00   0.50    0.05    -- -102.00  61.00-180.00   70
 17  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00-150.00   80
 18  ω    -67.00 -35.00   0.50    0.05    -- -102.00  61.00 -90.00   64
 19  ω    -59.00 -30.00   0.50    0.05    -- -102.00  55.00  65.00   58
 20  ω   -119.00 -75.00   0.50    0.05    --  -46.32 -55.00 -78.00   88
 21  ω   -174.00-145.00   0.50    0.05    -- -102.00 -55.00 -78.00   58
 22  ω   -173.00-133.00   0.50    0.05    -- -102.00 -45.00   0.00   80
 23  ω   -115.00 -90.00   0.50    0.05    -- -102.00 -45.00   0.00   50
 24  ω   -118.00 -75.00   0.50    0.05    --  -46.32-125.00  30.00   86
 25  ω   -111.00 -74.00   0.50    0.05    --  -46.32-125.00  60.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1166156000
_diffrn_orient_matrix_UB_12      0.0499475000
_diffrn_orient_matrix_UB_13      0.0721094000
_diffrn_orient_matrix_UB_21      -0.0811723000
_diffrn_orient_matrix_UB_22      -0.0058269000
_diffrn_orient_matrix_UB_23      0.1051567000
_diffrn_orient_matrix_UB_31      0.1099063000
_diffrn_orient_matrix_UB_32      -0.0573278000
_diffrn_orient_matrix_UB_33      0.0520739000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3591
_reflns_number_total             3952
_reflns_odcompleteness_completeness 99.86
_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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3952
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+0.8027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1012
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F00T) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F00K)
\\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F00I) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F00I(0.5) F00K(0.5) F00T(0.5) F1(0.5) F3(0.5) F4(0.5)
4.a Ternary CH refined with riding coordinates:
 C1(H1)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C007(H007), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.12445(4) 0.75623(2) 0.51694(3) 0.02442(12) Uani 1 1 d . . . . .
F00I F 0.5319(6) 0.4848(3) 0.1287(4) 0.084(2) Uani 0.5 1 d . U P A 2
F00K F 0.7064(7) 0.5450(3) 0.2247(6) 0.102(2) Uani 0.5 1 d . U P A 2
F00T F 0.6551(6) 0.4553(3) 0.2947(4) 0.0895(18) Uani 0.5 1 d . U P A 2
F1 F 0.5734(7) 0.44188(17) 0.2348(6) 0.102(2) Uani 0.5 1 d . U P A 1
F3 F 0.7265(5) 0.5207(3) 0.2762(5) 0.089(2) Uani 0.5 1 d . U P A 1
F4 F 0.5616(7) 0.5208(3) 0.1178(4) 0.094(2) Uani 0.5 1 d . U P A 1
O1 O 0.08498(12) 0.73633(5) 0.63168(9) 0.0306(2) Uani 1 1 d . . . . .
N1 N 0.12181(14) 0.63146(6) 0.42952(11) 0.0270(3) Uani 1 1 d . . . . .
C1 C 0.05375(16) 0.69685(7) 0.39472(13) 0.0250(3) Uani 1 1 d . . . . .
H1 H 0.079508 0.712224 0.318661 0.030 Uiso 1 1 calc R U . . .
C2 C -0.12225(17) 0.68490(8) 0.37753(14) 0.0299(3) Uani 1 1 d . . . . .
H2A H -0.176922 0.725963 0.391356 0.036 Uiso 1 1 calc R U . . .
H2B H -0.168285 0.668224 0.296111 0.036 Uiso 1 1 calc R U . . .
C3 C -0.13096(17) 0.63267(8) 0.47217(15) 0.0318(3) Uani 1 1 d . . . . .
H3A H -0.124503 0.653340 0.551318 0.038 Uiso 1 1 calc R U . . .
H3B H -0.228874 0.606898 0.449779 0.038 Uiso 1 1 calc R U . . .
C4 C 0.01079(18) 0.58893(7) 0.47329(15) 0.0317(3) Uani 1 1 d . . . . .
H4A H 0.056782 0.573060 0.555267 0.038 Uiso 1 1 calc R U . . .
H4B H -0.018627 0.550174 0.420254 0.038 Uiso 1 1 calc R U . . .
C5 C 0.24002(16) 0.60337(7) 0.38533(13) 0.0261(3) Uani 1 1 d . . . . .
C6 C 0.32502(18) 0.63893(8) 0.31550(14) 0.0305(3) Uani 1 1 d . . . . .
H6 H 0.305130 0.684739 0.300947 0.037 Uiso 1 1 calc R U . . .
C7 C 0.43684(18) 0.60768(8) 0.26816(14) 0.0333(3) Uani 1 1 d . . . . .
H7 H 0.491421 0.632160 0.219932 0.040 Uiso 1 1 calc R U . . .
C007 C 0.27995(17) 0.53656(7) 0.40981(14) 0.0291(3) Uani 1 1 d . . . . .
H007 H 0.228220 0.512005 0.459888 0.035 Uiso 1 1 calc R U . . .
C8 C 0.47115(18) 0.54083(8) 0.28986(14) 0.0318(3) Uani 1 1 d . U . . .
C9 C 0.39263(18) 0.50599(8) 0.36261(14) 0.0316(3) Uani 1 1 d . . . . .
H9 H 0.416789 0.460731 0.379967 0.038 Uiso 1 1 calc R U . . .
C10 C 0.5847(2) 0.50682(9) 0.23242(16) 0.0392(4) Uani 1 1 d . . . . .
C11 C 0.33265(17) 0.76175(7) 0.53365(13) 0.0274(3) Uani 1 1 d . . . . .
C12 C 0.40423(19) 0.80613(8) 0.46985(15) 0.0345(3) Uani 1 1 d . . . . .
H12 H 0.342853 0.835281 0.413252 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5662(2) 0.80740(9) 0.48969(16) 0.0402(4) Uani 1 1 d . . . . .
H13 H 0.615495 0.837658 0.446687 0.048 Uiso 1 1 calc R U . . .
C14 C 0.65572(19) 0.76484(9) 0.57169(16) 0.0399(4) Uani 1 1 d . . . . .
H14 H 0.766179 0.765932 0.584740 0.048 Uiso 1 1 calc R U . . .
C15 C 0.58494(19) 0.72059(9) 0.63491(16) 0.0397(4) Uani 1 1 d . . . . .
H15 H 0.646810 0.691344 0.691052 0.048 Uiso 1 1 calc R U . . .
C16 C 0.42396(18) 0.71901(8) 0.61622(15) 0.0336(3) Uani 1 1 d . . . . .
H16 H 0.375544 0.688726 0.659769 0.040 Uiso 1 1 calc R U . . .
C17 C 0.03433(16) 0.83388(7) 0.46290(13) 0.0269(3) Uani 1 1 d . . . . .
C18 C 0.01312(19) 0.85470(8) 0.34465(14) 0.0333(3) Uani 1 1 d . . . . .
H18 H 0.054101 0.829318 0.289196 0.040 Uiso 1 1 calc R U . . .
C19 C -0.0681(2) 0.91265(8) 0.30829(15) 0.0392(4) Uani 1 1 d . . . . .
H19 H -0.081821 0.927065 0.227822 0.047 Uiso 1 1 calc R U . . .
C20 C -0.12932(19) 0.94966(8) 0.38807(16) 0.0382(4) Uani 1 1 d . . . . .
H20 H -0.185994 0.988986 0.361986 0.046 Uiso 1 1 calc R U . . .
C21 C -0.10818(19) 0.92952(8) 0.50572(16) 0.0368(4) Uani 1 1 d . . . . .
H21 H -0.149700 0.955105 0.560631 0.044 Uiso 1 1 calc R U . . .
C22 C -0.02624(18) 0.87192(8) 0.54339(14) 0.0310(3) Uani 1 1 d . . . . .
H22 H -0.011201 0.858231 0.624357 0.037 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 1.4916(11) . ?
P1 C1 1.8443(15) . ?
P1 C11 1.8025(15) . ?
P1 C17 1.8040(15) . ?
F00I C10 1.258(5) . ?
F00K C10 1.339(6) . ?
F00T C10 1.334(4) . ?
F1 C10 1.317(4) . ?
F3 C10 1.267(5) . ?
F4 C10 1.315(5) . ?
N1 C1 1.4685(18) . ?
N1 C4 1.4726(18) . ?
N1 C5 1.3789(19) . ?
C1 H1 1.0000 . ?
C1 C2 1.5360(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.529(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.527(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.411(2) . ?
C5 C007 1.408(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.380(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.395(2) . ?
C007 H007 0.9500 . ?
C007 C9 1.379(2) . ?
C8 C9 1.390(2) . ?
C8 C10 1.485(2) . ?
C9 H9 0.9500 . ?
C11 C12 1.395(2) . ?
C11 C16 1.395(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(2) . ?
C17 C22 1.397(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(2) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C1 112.99(6) . . ?
O1 P1 C11 110.92(7) . . ?
O1 P1 C17 111.48(7) . . ?
C11 P1 C1 106.34(7) . . ?
C11 P1 C17 109.88(7) . . ?
C17 P1 C1 104.95(6) . . ?
C1 N1 C4 110.90(11) . . ?
C5 N1 C1 124.46(12) . . ?
C5 N1 C4 119.97(12) . . ?
P1 C1 H1 111.0 . . ?
N1 C1 P1 109.38(9) . . ?
N1 C1 H1 111.0 . . ?
N1 C1 C2 103.36(11) . . ?
C2 C1 P1 110.92(10) . . ?
C2 C1 H1 111.0 . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 C1 103.21(11) . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 C2 103.50(12) . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
N1 C4 C3 105.26(12) . . ?
N1 C4 H4A 110.7 . . ?
N1 C4 H4B 110.7 . . ?
C3 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C6 122.73(13) . . ?
N1 C5 C007 119.78(13) . . ?
C007 C5 C6 117.49(13) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.52(14) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.19(15) . . ?
C8 C7 H7 119.4 . . ?
C5 C007 H007 119.3 . . ?
C9 C007 C5 121.36(14) . . ?
C9 C007 H007 119.3 . . ?
C7 C8 C10 120.63(15) . . ?
C9 C8 C7 118.75(14) . . ?
C9 C8 C10 120.57(15) . . ?
C007 C9 C8 120.58(15) . . ?
C007 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
F00I C10 F00K 105.7(4) . . ?
F00I C10 F00T 105.0(4) . . ?
F00I C10 C8 116.3(3) . . ?
F00K C10 C8 113.0(3) . . ?
F00T C10 F00K 101.8(4) . . ?
F00T C10 C8 113.6(2) . . ?
F1 C10 C8 113.0(2) . . ?
F3 C10 F1 106.6(4) . . ?
F3 C10 F4 105.4(4) . . ?
F3 C10 C8 115.0(3) . . ?
F4 C10 F1 103.8(4) . . ?
F4 C10 C8 112.2(3) . . ?
C12 C11 P1 123.57(12) . . ?
C16 C11 P1 116.72(12) . . ?
C16 C11 C12 119.71(14) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.57(16) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.29(16) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.26(15) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.96(16) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.21(15) . . ?
C15 C16 H16 119.9 . . ?
C18 C17 P1 123.33(11) . . ?
C18 C17 C22 119.43(14) . . ?
C22 C17 P1 117.07(12) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.66(15) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.62(16) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.09(15) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.84(15) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.35(15) . . ?
C21 C22 H22 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 -83.02(12) . . . . ?
P1 C11 C12 C13 179.25(12) . . . . ?
P1 C11 C16 C15 -179.49(13) . . . . ?
P1 C17 C18 C19 174.96(13) . . . . ?
P1 C17 C22 C21 -174.80(12) . . . . ?
O1 P1 C1 N1 -58.76(11) . . . . ?
O1 P1 C1 C2 54.61(11) . . . . ?
O1 P1 C11 C12 -148.36(13) . . . . ?
O1 P1 C11 C16 31.14(14) . . . . ?
O1 P1 C17 C18 -160.83(12) . . . . ?
O1 P1 C17 C22 14.45(13) . . . . ?
N1 C1 C2 C3 34.10(14) . . . . ?
N1 C5 C6 C7 -176.63(14) . . . . ?
N1 C5 C007 C9 177.01(14) . . . . ?
C1 P1 C11 C12 88.42(14) . . . . ?
C1 P1 C11 C16 -92.08(13) . . . . ?
C1 P1 C17 C18 -38.18(14) . . . . ?
C1 P1 C17 C22 137.10(11) . . . . ?
C1 N1 C4 C3 -3.52(16) . . . . ?
C1 N1 C5 C6 10.2(2) . . . . ?
C1 N1 C5 C007 -169.95(13) . . . . ?
C1 C2 C3 C4 -36.40(15) . . . . ?
C2 C3 C4 N1 24.93(16) . . . . ?
C4 N1 C1 P1 98.98(12) . . . . ?
C4 N1 C1 C2 -19.22(15) . . . . ?
C4 N1 C5 C6 163.67(14) . . . . ?
C4 N1 C5 C007 -16.4(2) . . . . ?
C5 N1 C1 P1 -105.45(14) . . . . ?
C5 N1 C1 C2 136.35(14) . . . . ?
C5 N1 C4 C3 -160.34(13) . . . . ?
C5 C6 C7 C8 -1.3(2) . . . . ?
C5 C007 C9 C8 0.5(2) . . . . ?
C6 C5 C007 C9 -3.1(2) . . . . ?
C6 C7 C8 C9 -1.3(2) . . . . ?
C6 C7 C8 C10 176.25(15) . . . . ?
C7 C8 C9 C007 1.7(2) . . . . ?
C7 C8 C10 F00I -84.7(4) . . . . ?
C7 C8 C10 F00K 37.8(4) . . . . ?
C7 C8 C10 F00T 153.2(4) . . . . ?
C7 C8 C10 F1 -162.6(4) . . . . ?
C7 C8 C10 F3 74.7(4) . . . . ?
C7 C8 C10 F4 -45.7(4) . . . . ?
C007 C5 C6 C7 3.5(2) . . . . ?
C9 C8 C10 F00I 92.8(4) . . . . ?
C9 C8 C10 F00K -144.7(4) . . . . ?
C9 C8 C10 F00T -29.3(4) . . . . ?
C9 C8 C10 F1 14.9(4) . . . . ?
C9 C8 C10 F3 -107.8(4) . . . . ?
C9 C8 C10 F4 131.8(4) . . . . ?
C10 C8 C9 C007 -175.85(15) . . . . ?
C11 P1 C1 N1 63.14(11) . . . . ?
C11 P1 C1 C2 176.51(10) . . . . ?
C11 P1 C17 C18 75.78(14) . . . . ?
C11 P1 C17 C22 -108.94(12) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C16 C11 C12 C13 -0.2(2) . . . . ?
C17 P1 C1 N1 179.57(9) . . . . ?
C17 P1 C1 C2 -67.06(11) . . . . ?
C17 P1 C11 C12 -24.64(15) . . . . ?
C17 P1 C11 C16 154.85(12) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C17 C22 C21 0.7(2) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C17 -0.4(2) . . . . ?
C22 C17 C18 C19 -0.2(2) . . . . ?

_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 1.472
_oxdiff_exptl_absorpt_empirical_full_min 0.654
