# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2019

####################################################################### 
# 
# 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_P1-PF6
_database_code_depnum_ccdc_archive 'CCDC 1873171'
loop_
_audit_author_name
_audit_author_address
P1-PF6
; the Cambridge Structural Database
China
;
_audit_update_record             
;
2018-10-14 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H21 Br2 F6 N2 P'
_chemical_formula_weight         702.27

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   29.7525(17)
_cell_length_b                   5.9838(3)
_cell_length_c                   15.5910(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.639(2)
_cell_angle_gamma                90
_cell_volume                     2744.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    175(2)
_cell_measurement_reflns_used    10184
_cell_measurement_theta_min      2.997
_cell_measurement_theta_max      25.242

_exptl_crystal_description       Prism
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    3.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6079
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      175(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15694
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.770
_diffrn_reflns_theta_max         25.385
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5034
_reflns_number_gt                3685
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5034
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1379
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.33113(2) 0.34793(8) 0.43345(3) 0.03863(18) Uani 1 1 d . . . . .
Br2 Br 0.54481(2) 1.72676(10) 0.93869(3) 0.04544(19) Uani 1 1 d . . . . .
N1 N 0.14988(13) 1.8177(6) 0.7207(2) 0.0261(8) Uani 1 1 d . . . . .
N2 N 0.35544(12) 1.2460(6) 0.7088(2) 0.0201(7) Uani 1 1 d . . . . .
C1 C 0.15723(16) 1.7026(8) 0.6502(3) 0.0292(10) Uani 1 1 d . . . . .
H1A H 0.1344 1.6981 0.6007 0.035 Uiso 1 1 calc R U . . .
C2 C 0.19745(14) 1.5912(7) 0.6490(3) 0.0233(9) Uani 1 1 d . . . . .
H2B H 0.2021 1.5106 0.5986 0.028 Uiso 1 1 calc R U . . .
C3 C 0.23165(15) 1.5946(7) 0.7209(3) 0.0231(9) Uani 1 1 d . . . . .
C4 C 0.22271(18) 1.7176(8) 0.7923(3) 0.0349(11) Uani 1 1 d . . . . .
H4A H 0.2449 1.7252 0.8428 0.042 Uiso 1 1 calc R U . . .
C5 C 0.18209(17) 1.8281(8) 0.7905(3) 0.0318(11) Uani 1 1 d . . . . .
H5A H 0.1768 1.9130 0.8395 0.038 Uiso 1 1 calc R U . . .
C6 C 0.31583(14) 1.1683(7) 0.6665(2) 0.0185(9) Uani 1 1 d . . . . .
C7 C 0.27463(15) 1.2772(7) 0.6717(3) 0.0234(9) Uani 1 1 d . . . . .
H7A H 0.2469 1.2183 0.6420 0.028 Uiso 1 1 calc R U . . .
C8 C 0.27452(15) 1.4712(7) 0.7202(2) 0.0205(9) Uani 1 1 d . . . . .
C9 C 0.31555(14) 1.5499(7) 0.7636(2) 0.0199(9) Uani 1 1 d . . . . .
H9A H 0.3164 1.6814 0.7979 0.024 Uiso 1 1 calc R U . . .
C10 C 0.35590(14) 1.4331(7) 0.7563(2) 0.0206(9) Uani 1 1 d . . . . .
C11 C 0.10534(16) 1.9342(8) 0.7202(3) 0.0350(11) Uani 1 1 d . . . . .
H11A H 0.1027 1.9839 0.7798 0.042 Uiso 1 1 calc R U . . .
H11B H 0.1043 2.0685 0.6829 0.042 Uiso 1 1 calc R U . . .
C12 C 0.06622(16) 1.7850(7) 0.6876(3) 0.0267(10) Uani 1 1 d . . . . .
C13 C 0.05987(16) 1.5831(8) 0.7285(3) 0.0284(10) Uani 1 1 d . . . . .
H13A H 0.0806 1.5402 0.7781 0.034 Uiso 1 1 calc R U . . .
C14 C 0.02411(16) 1.4448(8) 0.6984(3) 0.0340(11) Uani 1 1 d . . . . .
H14A H 0.0208 1.3056 0.7261 0.041 Uiso 1 1 calc R U . . .
C15 C -0.00684(17) 1.5079(10) 0.6283(3) 0.0419(13) Uani 1 1 d . . . . .
H15A H -0.0318 1.4130 0.6079 0.050 Uiso 1 1 calc R U . . .
C16 C -0.00188(19) 1.7064(10) 0.5880(3) 0.0464(14) Uani 1 1 d . . . . .
H16A H -0.0238 1.7502 0.5402 0.056 Uiso 1 1 calc R U . . .
C17 C 0.03475(19) 1.8452(9) 0.6158(3) 0.0397(13) Uani 1 1 d . . . . .
H17A H 0.0384 1.9810 0.5860 0.048 Uiso 1 1 calc R U . . .
C18 C 0.31871(14) 0.9674(7) 0.6122(2) 0.0196(9) Uani 1 1 d . . . . .
C19 C 0.36098(15) 0.8690(7) 0.6073(3) 0.0245(9) Uani 1 1 d . . . . .
H19A H 0.3875 0.9282 0.6412 0.029 Uiso 1 1 calc R U . . .
C20 C 0.36476(17) 0.6877(7) 0.5542(3) 0.0293(10) Uani 1 1 d . . . . .
H20A H 0.3938 0.6254 0.5503 0.035 Uiso 1 1 calc R U . . .
C21 C 0.32624(16) 0.5977(7) 0.5068(2) 0.0234(9) Uani 1 1 d . . . . .
C22 C 0.28371(16) 0.6862(7) 0.5119(3) 0.0258(10) Uani 1 1 d . . . . .
H22A H 0.2572 0.6199 0.4804 0.031 Uiso 1 1 calc R U . . .
C23 C 0.28011(15) 0.8723(7) 0.5633(2) 0.0224(9) Uani 1 1 d . . . . .
H23A H 0.2511 0.9364 0.5653 0.027 Uiso 1 1 calc R U . . .
C24 C 0.40108(14) 1.5097(7) 0.7984(2) 0.0219(9) Uani 1 1 d . . . . .
C25 C 0.43902(17) 1.3743(8) 0.7969(3) 0.0338(11) Uani 1 1 d . . . . .
H25A H 0.4355 1.2340 0.7682 0.041 Uiso 1 1 calc R U . . .
C26 C 0.48188(17) 1.4406(9) 0.8368(3) 0.0410(13) Uani 1 1 d . . . . .
H26A H 0.5075 1.3478 0.8343 0.049 Uiso 1 1 calc R U . . .
C27 C 0.48680(16) 1.6416(8) 0.8798(3) 0.0276(10) Uani 1 1 d . . . . .
C28 C 0.45029(18) 1.7852(8) 0.8803(3) 0.0379(12) Uani 1 1 d . . . . .
H28A H 0.4543 1.9265 0.9082 0.046 Uiso 1 1 calc R U . . .
C29 C 0.40779(17) 1.7183(8) 0.8392(3) 0.0347(11) Uani 1 1 d . . . . .
H29A H 0.3826 1.8163 0.8388 0.042 Uiso 1 1 calc R U . . .
P1 P 0.15071(4) 0.3459(2) 0.96151(8) 0.0310(3) Uani 1 1 d . . . . .
F1 F 0.15826(13) 0.3547(5) 1.06498(17) 0.0576(10) Uani 1 1 d . . . . .
F2 F 0.14578(13) 0.3398(6) 0.85770(18) 0.0612(10) Uani 1 1 d . . . . .
F3 F 0.19820(11) 0.2185(6) 0.96671(19) 0.0555(9) Uani 1 1 d . . . . .
F4 F 0.10400(11) 0.4752(6) 0.9576(2) 0.0674(10) Uani 1 1 d . . . . .
F5 F 0.17624(11) 0.5813(5) 0.96097(19) 0.0511(8) Uani 1 1 d . . . . .
F6 F 0.12689(14) 0.1112(6) 0.9623(3) 0.0783(12) 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
Br1 C21 1.901(4) . ?
Br2 C27 1.899(4) . ?
N1 C5 1.339(6) . ?
N1 C1 1.342(6) . ?
N1 C11 1.497(6) . ?
N2 C10 1.342(5) . ?
N2 C6 1.344(5) . ?
C1 C2 1.372(6) . ?
C2 C3 1.395(6) . ?
C3 C4 1.393(6) . ?
C3 C8 1.475(6) . ?
C4 C5 1.374(7) . ?
C6 C7 1.401(6) . ?
C6 C18 1.481(5) . ?
C7 C8 1.386(6) . ?
C8 C9 1.386(6) . ?
C9 C10 1.408(6) . ?
C10 C24 1.477(6) . ?
C11 C12 1.494(7) . ?
C12 C13 1.392(6) . ?
C12 C17 1.395(6) . ?
C13 C14 1.374(7) . ?
C14 C15 1.372(7) . ?
C15 C16 1.362(8) . ?
C16 C17 1.387(8) . ?
C18 C23 1.400(6) . ?
C18 C19 1.401(6) . ?
C19 C20 1.380(6) . ?
C20 C21 1.377(6) . ?
C21 C22 1.385(6) . ?
C22 C23 1.386(6) . ?
C24 C25 1.393(6) . ?
C24 C29 1.402(6) . ?
C25 C26 1.390(7) . ?
C26 C27 1.374(7) . ?
C27 C28 1.386(7) . ?
C28 C29 1.388(7) . ?
P1 F6 1.574(4) . ?
P1 F4 1.584(3) . ?
P1 F1 1.596(3) . ?
P1 F3 1.597(3) . ?
P1 F5 1.601(3) . ?
P1 F2 1.603(3) . ?

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
C5 N1 C1 120.3(4) . . ?
C5 N1 C11 120.5(4) . . ?
C1 N1 C11 119.2(4) . . ?
C10 N2 C6 119.7(4) . . ?
N1 C1 C2 120.7(4) . . ?
C1 C2 C3 120.9(4) . . ?
C4 C3 C2 116.4(4) . . ?
C4 C3 C8 122.6(4) . . ?
C2 C3 C8 120.9(4) . . ?
C5 C4 C3 120.7(4) . . ?
N1 C5 C4 120.9(4) . . ?
N2 C6 C7 121.4(4) . . ?
N2 C6 C18 116.1(4) . . ?
C7 C6 C18 122.4(4) . . ?
C8 C7 C6 119.6(4) . . ?
C7 C8 C9 118.5(4) . . ?
C7 C8 C3 119.7(4) . . ?
C9 C8 C3 121.7(4) . . ?
C8 C9 C10 119.4(4) . . ?
N2 C10 C9 121.3(4) . . ?
N2 C10 C24 115.9(4) . . ?
C9 C10 C24 122.7(4) . . ?
C12 C11 N1 111.5(4) . . ?
C13 C12 C17 118.1(5) . . ?
C13 C12 C11 121.0(4) . . ?
C17 C12 C11 120.9(4) . . ?
C14 C13 C12 121.2(4) . . ?
C15 C14 C13 119.9(5) . . ?
C16 C15 C14 120.1(5) . . ?
C15 C16 C17 120.8(5) . . ?
C16 C17 C12 119.8(5) . . ?
C23 C18 C19 118.0(4) . . ?
C23 C18 C6 121.9(4) . . ?
C19 C18 C6 120.1(4) . . ?
C20 C19 C18 121.2(4) . . ?
C21 C20 C19 119.6(4) . . ?
C20 C21 C22 121.0(4) . . ?
C20 C21 Br1 119.8(3) . . ?
C22 C21 Br1 119.2(3) . . ?
C21 C22 C23 119.4(4) . . ?
C22 C23 C18 120.9(4) . . ?
C25 C24 C29 117.7(4) . . ?
C25 C24 C10 119.8(4) . . ?
C29 C24 C10 122.4(4) . . ?
C26 C25 C24 121.2(4) . . ?
C27 C26 C25 119.4(5) . . ?
C26 C27 C28 121.3(4) . . ?
C26 C27 Br2 119.6(4) . . ?
C28 C27 Br2 119.2(3) . . ?
C27 C28 C29 118.6(4) . . ?
C28 C29 C24 121.6(4) . . ?
F6 P1 F4 92.4(2) . . ?
F6 P1 F1 90.9(2) . . ?
F4 P1 F1 90.7(2) . . ?
F6 P1 F3 88.3(2) . . ?
F4 P1 F3 179.0(2) . . ?
F1 P1 F3 88.59(18) . . ?
F6 P1 F5 178.5(2) . . ?
F4 P1 F5 89.1(2) . . ?
F1 P1 F5 88.94(18) . . ?
F3 P1 F5 90.20(19) . . ?
F6 P1 F2 90.9(2) . . ?
F4 P1 F2 91.5(2) . . ?
F1 P1 F2 177.1(2) . . ?
F3 P1 F2 89.22(18) . . ?
F5 P1 F2 89.22(18) . . ?

_refine_diff_density_max         1.122
_refine_diff_density_min         -1.025
_refine_diff_density_rms         0.084

