# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_pyg201005
_audit_block_doi                 10.5517/ccdc.csd.cc29kwkb
_database_code_depnum_ccdc_archive 'CCDC 2132352'
loop_
_audit_author_name
_audit_author_address
'xiaofeng li'
;southwest university
China
;
_audit_update_record             
;
2022-01-03 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_audit_creation_date             2020-10-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 F6 O4 P'
_chemical_formula_sum            'C17 H19 F6 O4 P'
_chemical_formula_weight         432.29
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 P1'
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                   6.48901(10)
_cell_length_b                   9.77517(14)
_cell_length_c                   15.33782(18)
_cell_angle_alpha                90
_cell_angle_beta                 100.8299(13)
_cell_angle_gamma                90
_cell_volume                     955.57(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6729
_cell_measurement_temperature    291.28(10)
_cell_measurement_theta_max      71.6660
_cell_measurement_theta_min      5.3810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9473
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.807
_diffrn_reflns_theta_min         5.395
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.28(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  33.00   1.00    1.00    --  -35.97   0.00 150.00  138
  2  ω    -53.00  31.00   1.00    1.00    --  -35.97  57.00   0.00   84
  3  ω     24.00  90.00   1.00    1.00    --   35.97-126.00  60.00   66
  4  ω     24.00  90.00   1.00    1.00    --   35.97-126.00 120.00   66
  5  ω     38.00 129.00   1.00    1.68    --  107.97 -30.00 150.00   91
  6  ω     87.00 178.00   1.00    1.68    --  107.97  30.00 -30.00   91
  7  ω     40.00 125.00   1.00    1.68    --  107.97 -45.00   0.00   85
  8  ω    101.00 178.00   1.00    1.68    --  107.97 112.00-120.00   77
  9  ω     57.00 150.00   1.00    1.68    --  107.97 178.00 -90.00   93
 10  ω     70.00 178.00   1.00    1.68    --  107.97  15.00-120.00  108
 11  ω    101.00 178.00   1.00    1.68    --  107.97 112.00 -90.00   77
 12  ω    -63.00  32.00   1.00    1.00    --  -35.97  77.00-120.00   95
 13  ω   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00 120.00   84
 14  ω   -104.00  -9.00   1.00    1.00    --  -35.97 -77.00  30.00   95
 15  ω     70.00 178.00   1.00    1.68    --  107.97  15.00  90.00  108
 16  ω     39.00 110.00   1.00    1.68    --  107.97 -95.00 -60.00   71
 17  ω     81.00 176.00   1.00    1.68    --  107.97  77.00 150.00   95
 18  ω     91.00 176.00   1.00    1.68    --  107.97  45.00   0.00   85
 19  ω     39.00 110.00   1.00    1.68    --  107.97 -95.00-150.00   71
 20  ω     81.00 176.00   1.00    1.68    --  107.97  77.00 120.00   95
 21  ω    -53.00  31.00   1.00    1.00    --  -35.97  57.00-180.00   84
 22  ω      9.00 104.00   1.00    1.00    --   35.97  77.00-150.00   95
 23  ω      9.00 104.00   1.00    1.00    --   35.97  77.00 -60.00   95
 24  ω     87.00 162.00   1.00    1.68    --  107.97  30.00 -90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0197747000
_diffrn_orient_matrix_UB_12      -0.0182800000
_diffrn_orient_matrix_UB_13      -0.1009852000
_diffrn_orient_matrix_UB_21      -0.2157756000
_diffrn_orient_matrix_UB_22      0.0710116000
_diffrn_orient_matrix_UB_23      -0.0150401000
_diffrn_orient_matrix_UB_31      0.1071759000
_diffrn_orient_matrix_UB_32      0.1395036000
_diffrn_orient_matrix_UB_33      -0.0055938000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.686
_reflns_Friedel_fraction_full    0.797
_reflns_Friedel_fraction_max     0.772
_reflns_number_gt                3225
_reflns_number_total             3314
_reflns_odcompleteness_completeness 99.94
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1273 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   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.030
_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)+(0.1000P)²+0.1476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1355
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C13(H13)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P -0.62189(14) -0.49012(10) -0.66346(5) 0.0538(3) Uani 1 1 d . . . . .
O1 O -0.8331(5) -0.2165(3) -0.5939(2) 0.0667(8) Uani 1 1 d . . . . .
F4 F -1.2657(4) -0.5820(5) -0.1330(2) 0.1005(12) Uani 1 1 d . . . . .
O3 O -0.6122(6) -0.3748(4) -0.7321(2) 0.0800(10) Uani 1 1 d . . . . .
F6 F -1.0325(7) -0.7326(4) -0.0990(3) 0.1070(13) Uani 1 1 d . . . . .
C9 C -0.8204(5) -0.3281(4) -0.5596(2) 0.0430(7) Uani 1 1 d . . . . .
F3 F -0.4829(8) -0.2625(6) 0.01518(19) 0.1274(18) Uani 1 1 d . . . . .
F2 F -0.3060(5) -0.2649(6) -0.0871(3) 0.133(2) Uani 1 1 d . . . . .
C3 C -0.6215(5) -0.4120(4) -0.5563(2) 0.0410(6) Uani 1 1 d . . . . .
H3 H -0.504227 -0.347148 -0.546196 0.049 Uiso 1 1 calc R . . . .
C11 C -0.6488(6) -0.3620(4) -0.2135(2) 0.0487(7) Uani 1 1 d . . . . .
H11 H -0.556575 -0.309978 -0.239516 0.058 Uiso 1 1 calc R . . . .
O4 O -0.8600(6) -0.5332(5) -0.6892(2) 0.0889(13) Uani 1 1 d . . . . .
F5 F -1.0573(6) -0.5767(6) -0.0079(2) 0.1168(16) Uani 1 1 d . . . . .
C10 C -0.7871(5) -0.4517(4) -0.2653(2) 0.0457(7) Uani 1 1 d . . . . .
C15 C -0.9226(5) -0.5274(4) -0.2241(2) 0.0484(8) Uani 1 1 d . . . . .
H15 H -1.016626 -0.587759 -0.257445 0.058 Uiso 1 1 calc R . . . .
C13 C -0.7815(6) -0.4252(5) -0.0828(2) 0.0525(8) Uani 1 1 d . . . . .
H13 H -0.779180 -0.416555 -0.022283 0.063 Uiso 1 1 calc R . . . .
F1 F -0.5459(9) -0.1242(4) -0.0883(3) 0.1365(19) Uani 1 1 d . . . . .
C12 C -0.6477(6) -0.3497(4) -0.1234(2) 0.0517(8) Uani 1 1 d . . . . .
C16 C -0.4960(7) -0.2514(6) -0.0705(3) 0.0684(12) Uani 1 1 d . . . . .
C4 C -0.5743(6) -0.5195(4) -0.4827(2) 0.0512(8) Uani 1 1 d . . . . .
H4A H -0.437223 -0.558566 -0.483437 0.061 Uiso 1 1 calc R . . . .
H4B H -0.676602 -0.592582 -0.495816 0.061 Uiso 1 1 calc R . . . .
C5 C -0.5771(5) -0.4660(4) -0.3890(2) 0.0513(8) Uani 1 1 d . . . . .
H5A H -0.482700 -0.521203 -0.346466 0.062 Uiso 1 1 calc R . . . .
H5B H -0.524636 -0.372877 -0.384332 0.062 Uiso 1 1 calc R . . . .
C14 C -0.9196(5) -0.5141(4) -0.1339(2) 0.0517(8) Uani 1 1 d . . . . .
C17 C -1.0682(7) -0.5991(6) -0.0927(3) 0.0680(12) Uani 1 1 d . . . . .
C6 C -0.7953(5) -0.4683(4) -0.3645(2) 0.0460(7) Uani 1 1 d . . . . .
H6 H -0.855500 -0.558696 -0.380986 0.055 Uiso 1 1 calc R . . . .
C7 C -0.9470(5) -0.3625(5) -0.4148(2) 0.0553(9) Uani 1 1 d . . . . .
H7A H -0.888537 -0.271819 -0.401706 0.066 Uiso 1 1 calc R . . . .
H7B H -1.078399 -0.366729 -0.393375 0.066 Uiso 1 1 calc R . . . .
C8 C -0.9923(5) -0.3836(5) -0.5166(2) 0.0571(10) Uani 1 1 d . . . . .
H8A H -1.008954 -0.480599 -0.529384 0.069 Uiso 1 1 calc R . . . .
H8B H -1.123189 -0.338610 -0.541794 0.069 Uiso 1 1 calc R . . . .
C2 C -0.9473(11) -0.5966(9) -0.7703(4) 0.109(2) Uani 1 1 d . . . . .
H2A H -0.919723 -0.541587 -0.818663 0.164 Uiso 1 1 calc GR . . . .
H2B H -1.096148 -0.605879 -0.774436 0.164 Uiso 1 1 calc GR . . . .
H2C H -0.885688 -0.685366 -0.772946 0.164 Uiso 1 1 calc GR . . . .
C1 C -0.4209(10) -0.3355(8) -0.7579(5) 0.0951(18) Uani 1 1 d . . . . .
H1A H -0.450141 -0.299825 -0.817209 0.143 Uiso 1 1 calc GR . . . .
H1B H -0.330662 -0.413769 -0.755669 0.143 Uiso 1 1 calc GR . . . .
H1C H -0.352908 -0.266509 -0.718028 0.143 Uiso 1 1 calc GR . . . .
O2 O -0.4685(7) -0.5982(4) -0.6622(2) 0.0791(10) 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 O3 1.552(4) . ?
P1 C3 1.812(3) . ?
P1 O4 1.578(4) . ?
P1 O2 1.449(3) . ?
O1 C9 1.207(5) . ?
F4 C17 1.324(5) . ?
O3 C1 1.424(7) . ?
F6 C17 1.332(7) . ?
C9 C3 1.522(4) . ?
C9 C8 1.501(5) . ?
F3 C16 1.306(5) . ?
F2 C16 1.311(6) . ?
C3 C4 1.532(5) . ?
C11 C10 1.392(5) . ?
C11 C12 1.386(5) . ?
O4 C2 1.409(6) . ?
F5 C17 1.309(6) . ?
C10 C15 1.389(5) . ?
C10 C6 1.521(4) . ?
C15 C14 1.386(5) . ?
C13 C12 1.374(5) . ?
C13 C14 1.381(6) . ?
F1 C16 1.301(7) . ?
C12 C16 1.501(5) . ?
C4 C5 1.533(4) . ?
C5 C6 1.532(5) . ?
C14 C17 1.499(5) . ?
C6 C7 1.532(5) . ?
C7 C8 1.547(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 P1 C3 108.41(19) . . ?
O3 P1 O4 100.7(2) . . ?
O4 P1 C3 100.03(17) . . ?
O2 P1 O3 115.1(2) . . ?
O2 P1 C3 114.27(18) . . ?
O2 P1 O4 116.5(3) . . ?
C1 O3 P1 122.2(4) . . ?
O1 C9 C3 119.3(3) . . ?
O1 C9 C8 121.5(3) . . ?
C8 C9 C3 119.1(3) . . ?
C9 C3 P1 109.9(2) . . ?
C9 C3 C4 116.4(3) . . ?
C4 C3 P1 110.2(2) . . ?
C12 C11 C10 120.3(3) . . ?
C2 O4 P1 123.4(4) . . ?
C11 C10 C6 122.4(3) . . ?
C15 C10 C11 118.1(3) . . ?
C15 C10 C6 119.5(3) . . ?
C14 C15 C10 120.9(3) . . ?
C12 C13 C14 118.7(3) . . ?
C11 C12 C16 118.3(4) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 C16 120.4(3) . . ?
F3 C16 F2 107.6(4) . . ?
F3 C16 C12 113.7(4) . . ?
F2 C16 C12 112.1(4) . . ?
F1 C16 F3 104.9(5) . . ?
F1 C16 F2 105.2(5) . . ?
F1 C16 C12 112.7(4) . . ?
C3 C4 C5 114.9(3) . . ?
C6 C5 C4 113.5(3) . . ?
C15 C14 C17 118.6(4) . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 C17 120.7(4) . . ?
F4 C17 F6 104.8(5) . . ?
F4 C17 C14 112.1(4) . . ?
F6 C17 C14 112.2(4) . . ?
F5 C17 F4 108.0(4) . . ?
F5 C17 F6 105.0(5) . . ?
F5 C17 C14 114.0(4) . . ?
C10 C6 C5 112.5(3) . . ?
C10 C6 C7 109.3(3) . . ?
C5 C6 C7 113.8(3) . . ?
C6 C7 C8 113.6(3) . . ?
C9 C8 C7 112.3(3) . . ?

_shelx_SHELXL_version_number     2017/1

_olex2_date_sample_data_collection 2020-10-05
_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 1.437
_oxdiff_exptl_absorpt_empirical_full_min 0.707
