# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_r20200910c
_database_code_depnum_ccdc_archive 'CCDC 2082526'
loop_
_audit_author_name
_audit_author_address
'Shumei Xia'
;Nankai University
China
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2021-09-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H26 P4 Pd'
_chemical_formula_sum            'C27 H26 P4 Pd'
_chemical_formula_weight         580.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.4671(5)
_cell_length_b                   10.5451(6)
_cell_length_c                   14.4131(7)
_cell_angle_alpha                88.379(4)
_cell_angle_beta                 80.098(4)
_cell_angle_gamma                73.608(5)
_cell_volume                     1215.92(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8122
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      32.5950
_cell_measurement_theta_min      1.9910
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.819
_exptl_absorpt_coefficient_mu    1.041
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12663
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.014
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_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   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0765750000
_diffrn_orient_matrix_UB_12      0.0113794000
_diffrn_orient_matrix_UB_13      -0.0214282000
_diffrn_orient_matrix_UB_21      -0.0443504000
_diffrn_orient_matrix_UB_22      0.0544018000
_diffrn_orient_matrix_UB_23      -0.0241295000
_diffrn_orient_matrix_UB_31      -0.0048897000
_diffrn_orient_matrix_UB_32      0.0427676000
_diffrn_orient_matrix_UB_33      0.0381497000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4150
_reflns_number_total             4961
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.941
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4961
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.057
_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)+(0.0423P)²+3.6411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1177
_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:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27)
;
_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
Pd1 Pd 0.59806(4) 0.33586(3) 0.24421(2) 0.01587(12) Uani 1 1 d . . . . .
P1 P 0.74032(14) 0.48792(11) 0.21518(8) 0.0176(2) Uani 1 1 d . . . . .
P2 P 0.82697(13) 0.18633(11) 0.27806(8) 0.0170(2) Uani 1 1 d . . . . .
P3 P 0.45783(13) 0.17084(10) 0.27266(8) 0.0159(2) Uani 1 1 d . . . . .
P4 P 0.34468(14) 0.49508(11) 0.23080(10) 0.0250(3) Uani 1 1 d . . . . .
C1 C 0.6432(6) 0.6268(4) 0.1474(3) 0.0222(10) Uani 1 1 d . . . . .
C2 C 0.6245(6) 0.6021(5) 0.0558(4) 0.0306(11) Uani 1 1 d . . . . .
H2 H 0.664427 0.514557 0.030269 0.037 Uiso 1 1 calc R . . . .
C3 C 0.5479(7) 0.7045(5) 0.0018(4) 0.0340(12) Uani 1 1 d . . . . .
H3 H 0.534449 0.687726 -0.060318 0.041 Uiso 1 1 calc R . . . .
C4 C 0.4914(7) 0.8316(5) 0.0399(4) 0.0358(13) Uani 1 1 d . . . . .
H4 H 0.439815 0.902333 0.003025 0.043 Uiso 1 1 calc R . . . .
C5 C 0.5085(7) 0.8574(5) 0.1300(4) 0.0344(12) Uani 1 1 d . . . . .
H5 H 0.467207 0.945023 0.155441 0.041 Uiso 1 1 calc R . . . .
C6 C 0.5871(6) 0.7542(5) 0.1841(4) 0.0282(11) Uani 1 1 d . . . . .
H6 H 0.601793 0.771712 0.245874 0.034 Uiso 1 1 calc R . . . .
C7 C 0.7582(6) 0.5559(4) 0.3260(3) 0.0213(9) Uani 1 1 d . . . . .
C8 C 0.9009(8) 0.5829(7) 0.3420(4) 0.0557(19) Uani 1 1 d . . . . .
H8 H 0.994921 0.569831 0.292910 0.067 Uiso 1 1 calc R . . . .
C9 C 0.9074(9) 0.6291(9) 0.4295(5) 0.074(3) Uani 1 1 d . . . . .
H9 H 1.007549 0.645755 0.439900 0.089 Uiso 1 1 calc R . . . .
C10 C 0.7760(7) 0.6513(5) 0.5007(4) 0.0382(13) Uani 1 1 d . . . . .
H10 H 0.782893 0.683356 0.560409 0.046 Uiso 1 1 calc R . . . .
C11 C 0.6341(7) 0.6267(6) 0.4851(4) 0.0468(15) Uani 1 1 d . . . . .
H11 H 0.539833 0.642892 0.534188 0.056 Uiso 1 1 calc R . . . .
C12 C 0.6247(7) 0.5782(7) 0.3982(4) 0.0473(16) Uani 1 1 d . . . . .
H12 H 0.524677 0.560228 0.388850 0.057 Uiso 1 1 calc R . . . .
C13 C 0.9521(6) 0.4291(5) 0.1471(3) 0.0244(10) Uani 1 1 d . . . . .
H13A H 0.942962 0.432341 0.079452 0.029 Uiso 1 1 calc R . . . .
H13B H 1.014044 0.492524 0.158031 0.029 Uiso 1 1 calc R . . . .
C14 C 1.0578(6) 0.2906(5) 0.1664(4) 0.0285(11) Uani 1 1 d . . . . .
H14A H 1.045454 0.228124 0.119947 0.034 Uiso 1 1 calc R . . . .
H14B H 1.176586 0.290357 0.155179 0.034 Uiso 1 1 calc R . . . .
C15 C 1.0172(5) 0.2386(5) 0.2645(3) 0.0237(10) Uani 1 1 d . . . . .
H15A H 1.003030 0.308772 0.311979 0.028 Uiso 1 1 calc R . . . .
H15B H 1.111435 0.162804 0.275897 0.028 Uiso 1 1 calc R . . . .
C16 C 0.8928(5) 0.0351(4) 0.2071(3) 0.0211(9) Uani 1 1 d . . . . .
C17 C 0.8276(6) 0.0266(5) 0.1267(4) 0.0301(11) Uani 1 1 d . . . . .
H17 H 0.740578 0.098293 0.110699 0.036 Uiso 1 1 calc R . . . .
C18 C 0.8880(7) -0.0852(5) 0.0697(4) 0.0399(14) Uani 1 1 d . . . . .
H18 H 0.843075 -0.090184 0.014310 0.048 Uiso 1 1 calc R . . . .
C19 C 1.0142(7) -0.1903(5) 0.0929(4) 0.0367(13) Uani 1 1 d . . . . .
H19 H 1.054912 -0.267613 0.053810 0.044 Uiso 1 1 calc R . . . .
C20 C 1.0803(7) -0.1832(5) 0.1718(4) 0.0402(14) Uani 1 1 d . . . . .
H20 H 1.167668 -0.255166 0.187234 0.048 Uiso 1 1 calc R . . . .
C21 C 1.0197(6) -0.0703(5) 0.2297(4) 0.0344(12) Uani 1 1 d . . . . .
H21 H 1.065381 -0.065529 0.284868 0.041 Uiso 1 1 calc R . . . .
C22 C 0.7890(5) 0.1405(4) 0.4004(3) 0.0209(9) Uani 1 1 d . . . . .
C23 C 0.7331(6) 0.0309(5) 0.4264(3) 0.0263(10) Uani 1 1 d . . . . .
H23 H 0.721356 -0.025344 0.379233 0.032 Uiso 1 1 calc R . . . .
C24 C 0.6946(6) 0.0031(5) 0.5201(4) 0.0317(11) Uani 1 1 d . . . . .
H24 H 0.658719 -0.073329 0.537188 0.038 Uiso 1 1 calc R . . . .
C25 C 0.7075(7) 0.0847(5) 0.5887(4) 0.0342(12) Uani 1 1 d . . . . .
H25 H 0.678408 0.065563 0.653175 0.041 Uiso 1 1 calc R . . . .
C26 C 0.7626(8) 0.1944(6) 0.5651(4) 0.0428(14) Uani 1 1 d . . . . .
H26 H 0.773133 0.250183 0.612909 0.051 Uiso 1 1 calc R . . . .
C27 C 0.8027(7) 0.2230(5) 0.4699(4) 0.0334(12) Uani 1 1 d . . . . .
H27 H 0.839466 0.299012 0.452981 0.040 Uiso 1 1 calc R . . . .


_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
Pd1 P1 2.2529(11) . ?
Pd1 P2 2.2445(11) . ?
Pd1 P3 2.3589(10) . ?
Pd1 P4 2.3558(11) . ?
P1 C1 1.814(5) . ?
P1 C7 1.816(5) . ?
P1 C13 1.834(5) . ?
P2 C15 1.823(4) . ?
P2 C16 1.816(4) . ?
P2 C22 1.814(5) . ?
C1 C2 1.397(7) . ?
C1 C6 1.379(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(7) . ?
C7 C12 1.370(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.349(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.354(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(8) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.528(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.522(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.381(7) . ?
C16 C21 1.386(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.363(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.394(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(6) . ?
C22 C27 1.386(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.378(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.367(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.379(7) . ?
C26 H26 0.9500 . ?
C26 C27 1.401(7) . ?
C27 H27 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
P1 Pd1 P3 177.99(4) . . ?
P1 Pd1 P4 91.36(4) . . ?
P2 Pd1 P1 90.62(4) . . ?
P2 Pd1 P3 87.68(4) . . ?
P2 Pd1 P4 172.25(5) . . ?
P4 Pd1 P3 90.47(4) . . ?
C1 P1 Pd1 114.40(15) . . ?
C1 P1 C7 106.6(2) . . ?
C1 P1 C13 102.6(2) . . ?
C7 P1 Pd1 109.42(15) . . ?
C7 P1 C13 107.2(2) . . ?
C13 P1 Pd1 115.92(15) . . ?
C15 P2 Pd1 116.54(15) . . ?
C16 P2 Pd1 114.74(15) . . ?
C16 P2 C15 102.7(2) . . ?
C22 P2 Pd1 109.41(14) . . ?
C22 P2 C15 105.2(2) . . ?
C22 P2 C16 107.4(2) . . ?
C2 C1 P1 118.2(4) . . ?
C6 C1 P1 121.9(4) . . ?
C6 C1 C2 119.8(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(5) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(5) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(5) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.7(5) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 P1 123.2(4) . . ?
C12 C7 P1 118.6(4) . . ?
C12 C7 C8 118.2(5) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(5) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 118.9 . . ?
C10 C9 C8 122.1(6) . . ?
C10 C9 H9 118.9 . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.4(5) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(5) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 120.6(5) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
P1 C13 H13A 107.8 . . ?
P1 C13 H13B 107.8 . . ?
H13A C13 H13B 107.2 . . ?
C14 C13 P1 117.9(3) . . ?
C14 C13 H13A 107.8 . . ?
C14 C13 H13B 107.8 . . ?
C13 C14 H14A 108.2 . . ?
C13 C14 H14B 108.2 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 C13 116.2(4) . . ?
C15 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
P2 C15 H15A 109.4 . . ?
P2 C15 H15B 109.4 . . ?
C14 C15 P2 111.3(3) . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 P2 121.1(3) . . ?
C17 C16 C21 119.2(4) . . ?
C21 C16 P2 119.5(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(5) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(5) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(5) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.9(5) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 120.1(5) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 P2 121.5(4) . . ?
C27 C22 P2 119.1(4) . . ?
C27 C22 C23 119.2(4) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.4(5) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(5) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.5(5) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.3 . . ?
C25 C26 C27 119.4(5) . . ?
C27 C26 H26 120.3 . . ?
C22 C27 C26 120.1(5) . . ?
C22 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?

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
Pd1 P1 C1 C2 -62.9(4) . . . . ?
Pd1 P1 C1 C6 116.6(4) . . . . ?
Pd1 P1 C7 C8 139.7(5) . . . . ?
Pd1 P1 C7 C12 -38.4(5) . . . . ?
Pd1 P1 C13 C14 -38.1(4) . . . . ?
Pd1 P2 C15 C14 -54.2(4) . . . . ?
Pd1 P2 C16 C17 13.0(4) . . . . ?
Pd1 P2 C16 C21 -172.0(3) . . . . ?
Pd1 P2 C22 C23 94.1(4) . . . . ?
Pd1 P2 C22 C27 -80.5(4) . . . . ?
P1 C1 C2 C3 178.7(4) . . . . ?
P1 C1 C6 C5 -178.1(4) . . . . ?
P1 C7 C8 C9 -177.1(6) . . . . ?
P1 C7 C12 C11 178.3(5) . . . . ?
P1 C13 C14 C15 -26.8(6) . . . . ?
P2 C16 C17 C18 175.0(4) . . . . ?
P2 C16 C21 C20 -175.1(4) . . . . ?
P2 C22 C23 C24 -175.7(4) . . . . ?
P2 C22 C27 C26 175.5(4) . . . . ?
C1 P1 C7 C8 -96.1(5) . . . . ?
C1 P1 C7 C12 85.8(5) . . . . ?
C1 P1 C13 C14 -163.5(4) . . . . ?
C1 C2 C3 C4 0.4(8) . . . . ?
C2 C1 C6 C5 1.4(7) . . . . ?
C2 C3 C4 C5 -0.6(8) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C4 C5 C6 C1 -1.5(8) . . . . ?
C6 C1 C2 C3 -0.8(7) . . . . ?
C7 P1 C1 C2 176.0(4) . . . . ?
C7 P1 C1 C6 -4.5(4) . . . . ?
C7 P1 C13 C14 84.4(4) . . . . ?
C7 C8 C9 C10 -1.2(13) . . . . ?
C8 C7 C12 C11 0.0(9) . . . . ?
C8 C9 C10 C11 0.2(12) . . . . ?
C9 C10 C11 C12 0.8(10) . . . . ?
C10 C11 C12 C7 -1.0(10) . . . . ?
C12 C7 C8 C9 1.0(10) . . . . ?
C13 P1 C1 C2 63.5(4) . . . . ?
C13 P1 C1 C6 -117.0(4) . . . . ?
C13 P1 C7 C8 13.3(5) . . . . ?
C13 P1 C7 C12 -164.9(4) . . . . ?
C13 C14 C15 P2 76.0(5) . . . . ?
C15 P2 C16 C17 -114.5(4) . . . . ?
C15 P2 C16 C21 60.5(4) . . . . ?
C15 P2 C22 C23 -140.0(4) . . . . ?
C15 P2 C22 C27 45.5(4) . . . . ?
C16 P2 C15 C14 72.2(4) . . . . ?
C16 P2 C22 C23 -31.0(4) . . . . ?
C16 P2 C22 C27 154.4(4) . . . . ?
C16 C17 C18 C19 0.4(8) . . . . ?
C17 C16 C21 C20 0.0(8) . . . . ?
C17 C18 C19 C20 -0.6(8) . . . . ?
C18 C19 C20 C21 0.6(8) . . . . ?
C19 C20 C21 C16 -0.3(8) . . . . ?
C21 C16 C17 C18 -0.1(8) . . . . ?
C22 P2 C15 C14 -175.6(3) . . . . ?
C22 P2 C16 C17 134.8(4) . . . . ?
C22 P2 C16 C21 -50.2(4) . . . . ?
C22 C23 C24 C25 1.4(7) . . . . ?
C23 C22 C27 C26 0.8(8) . . . . ?
C23 C24 C25 C26 -1.3(8) . . . . ?
C24 C25 C26 C27 1.0(9) . . . . ?
C25 C26 C27 C22 -0.8(9) . . . . ?
C27 C22 C23 C24 -1.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.086
_oxdiff_exptl_absorpt_empirical_full_min 0.479
####################################################################### 
# 
# 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_2010227289-1
_database_code_depnum_ccdc_archive 'CCDC 2082527'
loop_
_audit_author_name
_audit_author_address
'Shumei Xia'
;Nankai University
China
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2021-09-09 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 F6 O2'
_chemical_formula_sum            'C17 H10 F6 O2'
_chemical_formula_weight         360.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.5094(3)
_cell_length_b                   15.2120(8)
_cell_length_c                   18.2863(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.429(6)
_cell_angle_gamma                90
_cell_volume                     1522.92(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3160
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.3280
_cell_measurement_theta_min      3.6760
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10535
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.389
_diffrn_reflns_theta_min         3.621
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  19.00   1.00    6.00    --    0.10 -77.00-120.00   64
  2  ω    -77.00 -22.00   1.00    6.00    --    0.10 -38.00-120.00   55
  3  ω      1.00  61.00   1.00    6.00    --    0.10  57.00   0.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0864257000
_diffrn_orient_matrix_UB_12      -0.0301265000
_diffrn_orient_matrix_UB_13      0.0116304000
_diffrn_orient_matrix_UB_21      -0.0241230000
_diffrn_orient_matrix_UB_22      -0.0160504000
_diffrn_orient_matrix_UB_23      -0.0364987000
_diffrn_orient_matrix_UB_31      0.0934654000
_diffrn_orient_matrix_UB_32      -0.0317846000
_diffrn_orient_matrix_UB_33      0.0074562000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3229
_reflns_number_total             4010
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.073
_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)+(0.0424P)²+0.4759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1026
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00M(H00M), C00N(H00N)
2.b Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_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
F1 F 0.4261(2) 0.45111(6) 0.68098(5) 0.0443(3) Uani 1 1 d . . . . .
F2 F 0.3522(2) 0.52818(6) 0.58277(6) 0.0475(3) Uani 1 1 d . . . . .
F3 F 0.7207(2) 0.49500(7) 0.62282(6) 0.0500(3) Uani 1 1 d . . . . .
F4 F 1.28755(17) 0.38688(6) 0.25230(5) 0.0325(2) Uani 1 1 d . . . . .
F5 F 0.99128(18) 0.37637(8) 0.16781(5) 0.0461(3) Uani 1 1 d . . . . .
F6 F 1.2811(2) 0.28098(7) 0.17556(6) 0.0475(3) Uani 1 1 d . . . . .
O1 O 0.11012(17) 0.09659(6) 0.51633(5) 0.0213(2) Uani 1 1 d . . . . .
O2 O 0.24406(17) -0.00042(6) 0.43813(5) 0.0212(2) Uani 1 1 d . . . . .
H004 H 0.133223 -0.030326 0.451440 0.032 Uiso 1 1 calc GR . . . .
C1 C 0.2463(2) 0.07701(8) 0.47041(6) 0.0155(2) Uani 1 1 d . . . . .
C2 C 0.4238(2) 0.14157(8) 0.44582(6) 0.0153(2) Uani 1 1 d . . . . .
C3 C 0.5504(2) 0.12025(8) 0.38962(7) 0.0169(2) Uani 1 1 d . . . . .
H00D H 0.534319 0.062327 0.373549 0.020 Uiso 1 1 calc R . . . .
C4 C 0.7109(2) 0.17593(8) 0.35002(6) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.6894(2) 0.26766(9) 0.34627(7) 0.0198(3) Uani 1 1 d . . . . .
H00H H 0.578584 0.296181 0.372902 0.024 Uiso 1 1 calc R . . . .
C6 C 0.8317(2) 0.31618(9) 0.30325(7) 0.0208(3) Uani 1 1 d . . . . .
H00G H 0.815010 0.376973 0.300700 0.025 Uiso 1 1 calc R . . . .
C7 C 0.9998(2) 0.27412(9) 0.26383(6) 0.0186(2) Uani 1 1 d . . . . .
C8 C 1.0266(2) 0.18359(9) 0.26766(7) 0.0212(3) Uani 1 1 d . . . . .
H00M H 1.141409 0.155621 0.242157 0.025 Uiso 1 1 calc R . . . .
C9 C 0.8805(2) 0.13492(9) 0.30990(7) 0.0197(2) Uani 1 1 d . . . . .
H00I H 0.895866 0.074043 0.311500 0.024 Uiso 1 1 calc R . . . .
C10 C 1.1407(2) 0.32856(9) 0.21497(7) 0.0228(3) Uani 1 1 d . . . . .
C11 C 0.4409(2) 0.22580(8) 0.48744(6) 0.0153(2) Uani 1 1 d . . . . .
C12 C 0.6514(2) 0.24462(8) 0.53423(7) 0.0187(2) Uani 1 1 d . . . . .
H00A H 0.781425 0.205296 0.538280 0.022 Uiso 1 1 calc R . . . .
C13 C 0.6679(2) 0.32195(9) 0.57491(7) 0.0221(3) Uani 1 1 d . . . . .
H00K H 0.808062 0.334212 0.606487 0.026 Uiso 1 1 calc R . . . .
C14 C 0.4740(3) 0.38087(8) 0.56820(7) 0.0220(3) Uani 1 1 d . . . . .
C15 C 0.2642(2) 0.36319(9) 0.52167(8) 0.0241(3) Uani 1 1 d . . . . .
H00N H 0.135592 0.403126 0.517119 0.029 Uiso 1 1 calc R . . . .
C16 C 0.2472(2) 0.28542(9) 0.48186(7) 0.0206(3) Uani 1 1 d . . . . .
H00J H 0.105239 0.272868 0.451138 0.025 Uiso 1 1 calc R . . . .
C17 C 0.4932(3) 0.46349(9) 0.61324(8) 0.0310(3) 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
F1 C17 1.3450(17) . ?
F2 C17 1.336(2) . ?
F3 C17 1.3348(19) . ?
F4 C10 1.3356(16) . ?
F5 C10 1.3385(17) . ?
F6 C10 1.3288(16) . ?
O1 C1 1.2241(15) . ?
O2 C1 1.3168(15) . ?
C2 C1 1.4902(16) . ?
C2 C3 1.3447(17) . ?
C4 C3 1.4722(16) . ?
C4 C5 1.4014(18) . ?
C4 C9 1.3979(17) . ?
C6 C5 1.3844(18) . ?
C7 C6 1.3912(18) . ?
C7 C8 1.3859(19) . ?
C7 C10 1.4975(17) . ?
C9 C8 1.3898(18) . ?
C11 C2 1.4879(16) . ?
C11 C12 1.3915(17) . ?
C11 C16 1.3956(17) . ?
C12 C13 1.3894(18) . ?
C13 C14 1.3889(19) . ?
C14 C15 1.383(2) . ?
C14 C17 1.4999(18) . ?
C16 C15 1.3868(19) . ?

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 C1 O2 123.32(11) . . ?
O1 C1 C2 121.33(11) . . ?
O2 C1 C2 115.33(10) . . ?
C3 C2 C1 119.05(11) . . ?
C3 C2 C11 126.15(11) . . ?
C11 C2 C1 114.79(10) . . ?
C2 C3 C4 128.96(11) . . ?
C5 C4 C3 123.01(11) . . ?
C9 C4 C3 118.36(11) . . ?
C9 C4 C5 118.46(11) . . ?
C6 C5 C4 120.56(12) . . ?
C5 C6 C7 120.09(12) . . ?
C6 C7 C10 118.32(12) . . ?
C8 C7 C6 120.27(12) . . ?
C8 C7 C10 121.35(12) . . ?
C7 C8 C9 119.50(12) . . ?
C8 C9 C4 121.10(12) . . ?
F4 C10 F5 105.19(12) . . ?
F4 C10 C7 112.78(10) . . ?
F5 C10 C7 111.24(11) . . ?
F6 C10 F4 106.45(11) . . ?
F6 C10 F5 107.45(11) . . ?
F6 C10 C7 113.23(12) . . ?
C12 C11 C2 119.49(11) . . ?
C12 C11 C16 119.29(11) . . ?
C16 C11 C2 121.20(11) . . ?
C13 C12 C11 120.23(12) . . ?
C14 C13 C12 119.70(12) . . ?
C13 C14 C17 119.08(13) . . ?
C15 C14 C13 120.69(12) . . ?
C15 C14 C17 120.23(13) . . ?
C14 C15 C16 119.45(12) . . ?
C15 C16 C11 120.64(12) . . ?
F1 C17 C14 112.25(11) . . ?
F2 C17 F1 106.26(12) . . ?
F2 C17 C14 112.72(13) . . ?
F3 C17 F1 106.28(14) . . ?
F3 C17 F2 106.49(12) . . ?
F3 C17 C14 112.35(12) . . ?

_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 1.268
_oxdiff_exptl_absorpt_empirical_full_min 0.842
