# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_0922-56
_database_code_depnum_ccdc_archive 'CCDC 2090628'
loop_
_audit_author_name
_audit_author_address
'xiujie jiang'
;Anhui university
China
;
_audit_update_record             
;
2021-06-17 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
_audit_creation_date             2021-05-17
_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         'F6 P, C29 H21 N2'
_chemical_formula_sum            'C29 H21 F6 N2 P'
_chemical_formula_weight         542.45
_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'
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                   10.285
_cell_length_b                   8.039
_cell_length_c                   29.472
_cell_angle_alpha                90
_cell_angle_beta                 99.66
_cell_angle_gamma                90
_cell_volume                     2402.2
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4523
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      4.36
_cell_measurement_theta_max      69.59
_shelx_estimated_absorpt_T_max   0.853
_shelx_estimated_absorpt_T_min   0.639
_exptl_absorpt_coefficient_mu    1.638
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0941
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10428
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         69.935
_diffrn_reflns_theta_min         4.361
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2555
_reflns_number_total             4356
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.355
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.012
_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)+(0.0709P)²+1.1414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1620
_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:
 C00C(H00C), C00F(H00F), C00H(H00H), C00I(H00I), C00K(H00K), C00M(H00M),
 C00N(H00N), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011)
2.b Idealised Me refined as rotating group:
 C012(H01A,H01B,H01C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
P001 P -0.24418(10) 0.28914(14) 0.54690(4) 0.0209(3) Uani 1 1 d . . . . .
F002 F -0.3593(2) 0.4206(3) 0.53172(8) 0.0288(6) Uani 1 1 d . . . . .
F003 F -0.2757(2) 0.2040(3) 0.49707(8) 0.0314(6) Uani 1 1 d . . . . .
F004 F -0.3471(3) 0.1649(3) 0.56430(8) 0.0332(6) Uani 1 1 d . . . . .
F005 F -0.1427(3) 0.4117(3) 0.52834(10) 0.0410(7) Uani 1 1 d . . . . .
F006 F -0.2128(3) 0.3721(3) 0.59633(9) 0.0400(7) Uani 1 1 d . . . . .
F007 F -0.1283(3) 0.1579(3) 0.56131(9) 0.0409(7) Uani 1 1 d . . . . .
N008 N -0.2516(3) 0.8012(4) 0.53683(11) 0.0212(8) Uani 1 1 d . . . . .
N009 N 0.6827(3) 0.9378(5) 0.68283(12) 0.0273(9) Uani 1 1 d . . . . .
C00A C 0.4953(4) 0.7817(5) 0.71355(13) 0.0168(8) Uani 1 1 d . . . . .
C00B C 0.6484(4) 0.7151(5) 0.78741(13) 0.0156(8) Uani 1 1 d . . . . .
C00C C 0.3488(4) 0.8658(5) 0.64049(13) 0.0178(9) Uani 1 1 d . . . . .
H00C H 0.420045 0.920207 0.631480 0.021 Uiso 1 1 calc R . . . .
C00D C 0.3662(4) 0.7831(5) 0.68297(12) 0.0145(8) Uani 1 1 d . . . . .
C00E C 0.8858(4) 0.6498(5) 0.80547(13) 0.0174(9) Uani 1 1 d . . . . .
C00F C 0.1354(4) 0.7080(5) 0.66675(13) 0.0178(8) Uani 1 1 d . . . . .
H00F H 0.063316 0.655781 0.675855 0.021 Uiso 1 1 calc R . . . .
C00G C 0.7824(4) 0.8031(5) 0.86104(13) 0.0197(9) Uani 1 1 d . . . . .
C00H C 0.7604(4) 0.5520(5) 0.73266(13) 0.0183(9) Uani 1 1 d . . . . .
H00H H 0.681941 0.545280 0.711812 0.022 Uiso 1 1 calc R . . . .
C00I C 0.8927(4) 0.7347(5) 0.84706(13) 0.0190(9) Uani 1 1 d . . . . .
H00I H 0.974161 0.745695 0.866041 0.023 Uiso 1 1 calc R . . . .
C00J C -0.0084(4) 0.7894(5) 0.59384(13) 0.0169(8) Uani 1 1 d . . . . .
C00K C 0.9986(4) 0.5712(5) 0.79320(15) 0.0219(9) Uani 1 1 d . . . . .
H00K H 1.078763 0.578065 0.813139 0.026 Uiso 1 1 calc R . . . .
C00L C 0.6570(4) 0.7915(5) 0.83133(13) 0.0180(8) Uani 1 1 d . . . . .
C00M C 0.5214(4) 0.7168(5) 0.75682(13) 0.0167(8) Uani 1 1 d . . . . .
H00M H 0.450908 0.668442 0.767988 0.020 Uiso 1 1 calc R . . . .
C00N C -0.0194(4) 0.7941(5) 0.54586(14) 0.0216(9) Uani 1 1 d . . . . .
H00N H 0.056347 0.793593 0.532512 0.026 Uiso 1 1 calc R . . . .
C00O C 0.7624(4) 0.6413(5) 0.77463(13) 0.0170(8) Uani 1 1 d . . . . .
C00P C 0.2561(4) 0.7041(5) 0.69550(13) 0.0180(8) Uani 1 1 d . . . . .
H00P H 0.264343 0.648445 0.723507 0.022 Uiso 1 1 calc R . . . .
C00Q C -0.2448(4) 0.7962(5) 0.58212(14) 0.0216(9) Uani 1 1 d . . . . .
H00Q H -0.322396 0.797220 0.594385 0.026 Uiso 1 1 calc R . . . .
C00R C 0.6008(4) 0.8660(5) 0.69635(13) 0.0188(9) Uani 1 1 d . . . . .
C00S C -0.1392(4) 0.7995(5) 0.51877(14) 0.0221(9) Uani 1 1 d . . . . .
H00S H -0.144374 0.801961 0.486971 0.027 Uiso 1 1 calc R . . . .
C00T C -0.1260(4) 0.7893(5) 0.61138(13) 0.0184(8) Uani 1 1 d . . . . .
H00T H -0.124059 0.784652 0.643016 0.022 Uiso 1 1 calc R . . . .
C00U C 0.1197(4) 0.7890(5) 0.62413(13) 0.0174(8) Uani 1 1 d . . . . .
C00V C 0.8696(4) 0.4770(5) 0.72242(14) 0.0227(9) Uani 1 1 d . . . . .
H00V H 0.864944 0.418222 0.695006 0.027 Uiso 1 1 calc R . . . .
C00W C 0.2293(4) 0.8682(5) 0.61205(14) 0.0185(9) Uani 1 1 d . . . . .
H00W H 0.221007 0.923826 0.584054 0.022 Uiso 1 1 calc R . . . .
C00X C 0.5569(5) 0.9359(5) 0.88866(15) 0.0296(11) Uani 1 1 d . . . . .
H00X H 0.481931 0.976545 0.898684 0.036 Uiso 1 1 calc R . . . .
C00Y C 0.5448(4) 0.8573(5) 0.84763(13) 0.0209(9) Uani 1 1 d . . . . .
H00Y H 0.461759 0.846007 0.829725 0.025 Uiso 1 1 calc R . . . .
C00Z C 0.9924(4) 0.4874(5) 0.75352(14) 0.0239(10) Uani 1 1 d . . . . .
H00Z H 1.067385 0.436251 0.746246 0.029 Uiso 1 1 calc R . . . .
C010 C 0.6811(5) 0.9572(6) 0.91646(15) 0.0319(11) Uani 1 1 d . . . . .
H010 H 0.688168 1.015836 0.943965 0.038 Uiso 1 1 calc R . . . .
C011 C 0.7903(5) 0.8923(5) 0.90320(14) 0.0270(10) Uani 1 1 d . . . . .
H011 H 0.871830 0.906105 0.921925 0.032 Uiso 1 1 calc R . . . .
C012 C -0.3809(4) 0.8084(6) 0.50637(15) 0.0268(10) Uani 1 1 d . . . . .
H01A H -0.414348 0.697583 0.500432 0.040 Uiso 1 1 calc GR . . . .
H01B H -0.371182 0.860637 0.477848 0.040 Uiso 1 1 calc GR . . . .
H01C H -0.441462 0.871502 0.521018 0.040 Uiso 1 1 calc GR . . . .


_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
P001 F002 1.594(3) . ?
P001 F003 1.603(3) . ?
P001 F004 1.601(3) . ?
P001 F005 1.597(3) . ?
P001 F006 1.585(3) . ?
P001 F007 1.595(3) . ?
N008 C00Q 1.326(5) . ?
N008 C00S 1.351(5) . ?
N008 C012 1.476(5) . ?
N009 C00R 1.146(5) . ?
C00A C00D 1.474(5) . ?
C00A C00M 1.362(5) . ?
C00A C00R 1.441(6) . ?
C00B C00L 1.422(5) . ?
C00B C00M 1.458(5) . ?
C00B C00O 1.420(5) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.402(5) . ?
C00C C00W 1.367(5) . ?
C00D C00P 1.401(5) . ?
C00E C00I 1.394(6) . ?
C00E C00K 1.421(6) . ?
C00E C00O 1.433(5) . ?
C00F H00F 0.9300 . ?
C00F C00P 1.380(5) . ?
C00F C00U 1.400(6) . ?
C00G C00I 1.385(6) . ?
C00G C00L 1.435(5) . ?
C00G C011 1.425(6) . ?
C00H H00H 0.9300 . ?
C00H C00O 1.427(5) . ?
C00H C00V 1.353(6) . ?
C00I H00I 0.9300 . ?
C00J C00N 1.400(6) . ?
C00J C00T 1.393(5) . ?
C00J C00U 1.463(5) . ?
C00K H00K 0.9300 . ?
C00K C00Z 1.342(6) . ?
C00L C00Y 1.424(6) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00N C00S 1.351(5) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00T 1.373(5) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00U C00W 1.391(6) . ?
C00V H00V 0.9300 . ?
C00V C00Z 1.433(6) . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
C00X C00Y 1.351(6) . ?
C00X C010 1.408(7) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C010 H010 0.9300 . ?
C010 C011 1.354(7) . ?
C011 H011 0.9300 . ?
C012 H01A 0.9600 . ?
C012 H01B 0.9600 . ?
C012 H01C 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
F002 P001 F003 89.99(14) . . ?
F002 P001 F004 90.22(14) . . ?
F002 P001 F005 89.55(14) . . ?
F002 P001 F007 179.09(16) . . ?
F004 P001 F003 89.11(14) . . ?
F005 P001 F003 89.58(14) . . ?
F005 P001 F004 178.66(15) . . ?
F006 P001 F002 90.34(14) . . ?
F006 P001 F003 179.60(16) . . ?
F006 P001 F004 90.66(15) . . ?
F006 P001 F005 90.66(16) . . ?
F006 P001 F007 90.35(14) . . ?
F007 P001 F003 89.33(14) . . ?
F007 P001 F004 90.38(15) . . ?
F007 P001 F005 89.84(15) . . ?
C00Q N008 C00S 119.5(3) . . ?
C00Q N008 C012 120.2(4) . . ?
C00S N008 C012 120.3(3) . . ?
C00M C00A C00D 126.2(4) . . ?
C00M C00A C00R 117.9(3) . . ?
C00R C00A C00D 115.8(3) . . ?
C00L C00B C00M 118.1(3) . . ?
C00O C00B C00L 119.6(3) . . ?
C00O C00B C00M 122.3(3) . . ?
C00D C00C H00C 119.3 . . ?
C00W C00C H00C 119.3 . . ?
C00W C00C C00D 121.4(4) . . ?
C00C C00D C00A 121.1(3) . . ?
C00P C00D C00A 121.4(3) . . ?
C00P C00D C00C 117.5(3) . . ?
C00I C00E C00K 121.2(4) . . ?
C00I C00E C00O 119.4(4) . . ?
C00K C00E C00O 119.4(4) . . ?
C00P C00F H00F 119.4 . . ?
C00P C00F C00U 121.2(4) . . ?
C00U C00F H00F 119.4 . . ?
C00I C00G C00L 119.4(4) . . ?
C00I C00G C011 122.0(4) . . ?
C011 C00G C00L 118.6(4) . . ?
C00O C00H H00H 119.1 . . ?
C00V C00H H00H 119.1 . . ?
C00V C00H C00O 121.7(4) . . ?
C00E C00I H00I 118.9 . . ?
C00G C00I C00E 122.2(4) . . ?
C00G C00I H00I 118.9 . . ?
C00N C00J C00U 121.9(3) . . ?
C00T C00J C00N 116.6(3) . . ?
C00T C00J C00U 121.5(3) . . ?
C00E C00K H00K 119.2 . . ?
C00Z C00K C00E 121.6(4) . . ?
C00Z C00K H00K 119.2 . . ?
C00B C00L C00G 119.7(4) . . ?
C00B C00L C00Y 122.5(4) . . ?
C00Y C00L C00G 117.8(4) . . ?
C00A C00M C00B 126.7(4) . . ?
C00A C00M H00M 116.6 . . ?
C00B C00M H00M 116.6 . . ?
C00J C00N H00N 119.7 . . ?
C00S C00N C00J 120.6(4) . . ?
C00S C00N H00N 119.7 . . ?
C00B C00O C00E 119.6(4) . . ?
C00B C00O C00H 123.2(3) . . ?
C00H C00O C00E 117.2(4) . . ?
C00D C00P H00P 119.6 . . ?
C00F C00P C00D 120.7(4) . . ?
C00F C00P H00P 119.6 . . ?
N008 C00Q H00Q 119.2 . . ?
N008 C00Q C00T 121.6(4) . . ?
C00T C00Q H00Q 119.2 . . ?
N009 C00R C00A 177.8(5) . . ?
N008 C00S C00N 121.5(4) . . ?
N008 C00S H00S 119.2 . . ?
C00N C00S H00S 119.2 . . ?
C00J C00T H00T 119.9 . . ?
C00Q C00T C00J 120.2(4) . . ?
C00Q C00T H00T 119.9 . . ?
C00F C00U C00J 120.3(4) . . ?
C00W C00U C00F 117.8(4) . . ?
C00W C00U C00J 121.9(4) . . ?
C00H C00V H00V 119.8 . . ?
C00H C00V C00Z 120.4(4) . . ?
C00Z C00V H00V 119.8 . . ?
C00C C00W C00U 121.4(4) . . ?
C00C C00W H00W 119.3 . . ?
C00U C00W H00W 119.3 . . ?
C00Y C00X H00X 119.5 . . ?
C00Y C00X C010 121.1(4) . . ?
C010 C00X H00X 119.5 . . ?
C00L C00Y H00Y 119.4 . . ?
C00X C00Y C00L 121.2(4) . . ?
C00X C00Y H00Y 119.4 . . ?
C00K C00Z C00V 119.7(4) . . ?
C00K C00Z H00Z 120.2 . . ?
C00V C00Z H00Z 120.2 . . ?
C00X C010 H010 120.0 . . ?
C011 C010 C00X 120.0(4) . . ?
C011 C010 H010 120.0 . . ?
C00G C011 H011 119.4 . . ?
C010 C011 C00G 121.1(4) . . ?
C010 C011 H011 119.4 . . ?
N008 C012 H01A 109.5 . . ?
N008 C012 H01B 109.5 . . ?
N008 C012 H01C 109.5 . . ?
H01A C012 H01B 109.5 . . ?
H01A C012 H01C 109.5 . . ?
H01B C012 H01C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_0514-1
_database_code_depnum_ccdc_archive 'CCDC 2090629'
loop_
_audit_author_name
_audit_author_address
'xiujie jiang'
;Anhui university
China
;
_audit_update_record             
;
2021-06-17 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
_audit_creation_date             2021-05-17
_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         'F6 P, C29 H23 N2 O2'
_chemical_formula_sum            'C29 H23 F6 N2 O2 P'
_chemical_formula_weight         576.46
_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      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                   9.1654(6)
_cell_length_b                   11.5906(7)
_cell_length_c                   12.2355(8)
_cell_angle_alpha                96.138(5)
_cell_angle_beta                 97.787(5)
_cell_angle_gamma                91.155(5)
_cell_volume                     1279.65(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5966
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      28.84
_cell_measurement_theta_max      68.98
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.640
_exptl_absorpt_coefficient_mu    1.632
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10292
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.533
_diffrn_reflns_theta_min         3.838
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3896
_reflns_number_total             4539
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         1.229
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         4539
_refine_ls_number_restraints     120
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0786
_refine_ls_restrained_S_all      1.077
_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)+(0.1756P)²+0.8522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2154
_refine_ls_wR_factor_ref         0.2348
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 P001-F2 \\sim P001-F00B \\sim P001-F008 \\sim P001-F00C \\sim P001-F002 \\sim
P001-F4 \\sim P001-F0 ~
 P001-F006 \\sim P001-F007 \\sim P001-F1 \\sim P001-F004 \\sim P001-F3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F00C \\sim F00B \\sim F4 \\sim F002 \\sim F2 \\sim F008 \\sim F3 \\sim F004
\\sim F1 \\sim F007 \\sim F0 \\sim F006: within 2A with sigma of 0.001 and
sigma for terminal atoms of 0.002
4. Others
 Sof(F0)=Sof(F1)=Sof(F00C)=Sof(F2)=Sof(F3)=Sof(F4)=1-FVAR(1)
 Sof(F002)=Sof(F004)=Sof(F006)=Sof(F007)=Sof(F008)=Sof(F00B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C00M(H00M)
5.b Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00L(H00L), C00N(H00N), C00P(H00P), C00Q(H00Q), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C014(H014)
5.c X=CH2 refined with riding coordinates:
 N009(H00A,H00B)
5.d Idealised Me refined as rotating group:
 C013(H01A,H01B,H01C)
;
_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
P001 P 0.82353(9) 0.84961(7) 0.79437(6) 0.0327(3) Uani 1 1 d D . . . .
F002 F 0.7937(19) 0.9782(11) 0.8472(15) 0.034(2) Uani 0.631(9) 1 d D U P A 1
O003 O 0.3369(2) 0.48601(16) 0.51821(16) 0.0254(5) Uani 1 1 d . . . . .
F004 F 0.8437(9) 0.7160(5) 0.7498(5) 0.0441(10) Uani 0.631(9) 1 d D U P A 1
O005 O 0.3495(2) 0.73744(18) 0.72016(18) 0.0337(5) Uani 1 1 d . . . . .
F006 F 0.7088(9) 0.8072(5) 0.8732(7) 0.0447(11) Uani 0.631(9) 1 d D U P A 1
F007 F 0.6978(6) 0.8609(6) 0.6937(4) 0.0431(10) Uani 0.631(9) 1 d D U P A 1
F008 F 0.9501(5) 0.8356(5) 0.9009(4) 0.0419(10) Uani 0.631(9) 1 d D U P A 1
N009 N 0.5247(3) 0.6155(2) 0.6739(2) 0.0289(6) Uani 1 1 d . . . . .
H00A H 0.592342 0.650729 0.722230 0.035 Uiso 1 1 calc R . . . .
H00B H 0.545358 0.555533 0.631756 0.035 Uiso 1 1 calc R . . . .
N00A N -0.2582(3) 1.0026(2) 0.1606(2) 0.0308(6) Uani 1 1 d . . . . .
F00B F 0.9472(6) 0.8937(4) 0.7288(4) 0.0444(8) Uani 0.631(9) 1 d D U P A 1
C00C C -0.0999(3) 0.8576(2) 0.2961(2) 0.0248(6) Uani 1 1 d . . . . .
C00D C -0.0100(3) 0.7843(2) 0.3679(2) 0.0241(6) Uani 1 1 d . . . . .
C00E C 0.1719(3) 0.6511(2) 0.5063(2) 0.0237(6) Uani 1 1 d . . . . .
C00F C 0.3886(3) 0.6536(2) 0.6643(2) 0.0251(6) Uani 1 1 d . . . . .
C00G C 0.2703(3) 0.4502(2) 0.8020(2) 0.0281(6) Uani 1 1 d . . . . .
C00H C 0.2772(3) 0.5829(2) 0.5771(2) 0.0240(6) Uani 1 1 d . . . . .
C00I C 0.3051(3) 0.4083(2) 0.6968(2) 0.0256(6) Uani 1 1 d . . . . .
C00J C 0.1553(3) 0.6263(3) 0.3907(2) 0.0284(6) Uani 1 1 d . . . . .
H00J H 0.205023 0.565010 0.359082 0.034 Uiso 1 1 calc R . . . .
C00K C 0.4015(3) 0.3169(2) 0.6842(2) 0.0282(6) Uani 1 1 d . . . . .
C00L C 0.0918(3) 0.7393(3) 0.5516(2) 0.0280(6) Uani 1 1 d . . . . .
H00L H 0.098216 0.754564 0.628360 0.034 Uiso 1 1 calc R . . . .
C00M C 0.2377(3) 0.4620(2) 0.5969(2) 0.0239(6) Uani 1 1 d . . . . .
H00M H 0.138416 0.432796 0.564615 0.029 Uiso 1 1 calc R . . . .
C00N C -0.2775(3) 1.0059(2) 0.2683(2) 0.0293(6) Uani 1 1 d . . . . .
H00N H -0.343865 1.056577 0.296763 0.035 Uiso 1 1 calc R . . . .
C00O C 0.3423(4) 0.4020(3) 0.8982(3) 0.0347(7) Uani 1 1 d . . . . .
C00P C 0.0663(3) 0.6917(3) 0.3232(2) 0.0277(6) Uani 1 1 d . . . . .
H00P H 0.056797 0.673782 0.246596 0.033 Uiso 1 1 calc R . . . .
C00Q C 0.0020(3) 0.8052(3) 0.4840(2) 0.0282(6) Uani 1 1 d . . . . .
H00Q H -0.051016 0.864218 0.516024 0.034 Uiso 1 1 calc R . . . .
C00R C 0.4762(3) 0.2727(3) 0.7819(3) 0.0337(7) Uani 1 1 d . . . . .
C00S C -0.2001(3) 0.9352(2) 0.3357(2) 0.0282(6) Uani 1 1 d . . . . .
H00S H -0.214585 0.938792 0.409779 0.034 Uiso 1 1 calc R . . . .
C00T C -0.0854(4) 0.8562(3) 0.1829(2) 0.0331(7) Uani 1 1 d . . . . .
H00T H -0.021545 0.805369 0.151404 0.040 Uiso 1 1 calc R . . . .
C00U C 0.4286(3) 0.2621(3) 0.5776(3) 0.0320(7) Uani 1 1 d . . . . .
H00U H 0.379712 0.287139 0.513143 0.038 Uiso 1 1 calc R . . . .
C00V C 0.1656(3) 0.5376(3) 0.8180(3) 0.0321(7) Uani 1 1 d . . . . .
H00V H 0.117508 0.569366 0.756911 0.039 Uiso 1 1 calc R . . . .
C00W C -0.1651(4) 0.9298(3) 0.1189(2) 0.0368(7) Uani 1 1 d . . . . .
H00W H -0.153400 0.928412 0.044493 0.044 Uiso 1 1 calc R . . . .
C00X C 0.1350(4) 0.5750(3) 0.9211(3) 0.0400(8) Uani 1 1 d . . . . .
H00X H 0.066087 0.631969 0.929741 0.048 Uiso 1 1 calc R . . . .
C00Y C 0.4446(4) 0.3167(3) 0.8857(3) 0.0379(8) Uani 1 1 d . . . . .
H00Y H 0.493308 0.288341 0.948560 0.045 Uiso 1 1 calc R . . . .
C00Z C 0.3068(4) 0.4458(3) 1.0054(3) 0.0435(9) Uani 1 1 d . . . . .
H00Z H 0.353639 0.416568 1.068408 0.052 Uiso 1 1 calc R . . . .
C010 C 0.5785(4) 0.1821(3) 0.7684(3) 0.0415(8) Uani 1 1 d . . . . .
H010 H 0.628977 0.154369 0.830840 0.050 Uiso 1 1 calc R . . . .
C011 C 0.5240(4) 0.1750(3) 0.5697(3) 0.0423(8) Uani 1 1 d . . . . .
H011 H 0.537852 0.139989 0.500087 0.051 Uiso 1 1 calc R . . . .
C012 C 0.2074(5) 0.5279(3) 1.0164(3) 0.0462(9) Uani 1 1 d . . . . .
H012 H 0.185507 0.554498 1.086520 0.055 Uiso 1 1 calc R . . . .
C013 C -0.3369(4) 1.0836(3) 0.0891(3) 0.0420(8) Uani 1 1 d . . . . .
H01A H -0.431570 1.098399 0.111883 0.063 Uiso 1 1 calc GR . . . .
H01B H -0.349624 1.049610 0.013234 0.063 Uiso 1 1 calc GR . . . .
H01C H -0.280341 1.155287 0.095972 0.063 Uiso 1 1 calc GR . . . .
C014 C 0.6030(4) 0.1362(3) 0.6660(4) 0.0465(9) Uani 1 1 d . . . . .
H014 H 0.671976 0.079081 0.658929 0.056 Uiso 1 1 calc R . . . .
F0 F 0.6638(10) 0.8674(10) 0.7200(8) 0.0425(14) Uani 0.369(9) 1 d D U P A 2
F1 F 0.8426(16) 0.7307(9) 0.7197(8) 0.0443(14) Uani 0.369(9) 1 d D U P A 2
F00C F 0.8966(10) 0.9176(7) 0.7037(6) 0.0426(10) Uani 0.369(9) 1 d D U P A 2
F2 F 0.9728(10) 0.8379(10) 0.8687(7) 0.0443(11) Uani 0.369(9) 1 d D U P A 2
F3 F 0.7198(17) 0.7817(10) 0.8608(13) 0.0449(11) Uani 0.369(9) 1 d D U P A 2
F4 F 0.820(4) 0.9759(18) 0.862(3) 0.033(2) Uani 0.369(9) 1 d D U P A 2


_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
P001 F002 1.604(8) . ?
P001 F004 1.609(6) . ?
P001 F006 1.623(6) . ?
P001 F007 1.587(5) . ?
P001 F008 1.648(5) . ?
P001 F00B 1.581(4) . ?
P001 F0 1.645(9) . ?
P001 F1 1.596(10) . ?
P001 F00C 1.634(7) . ?
P001 F2 1.553(9) . ?
P001 F3 1.581(11) . ?
P001 F4 1.604(13) . ?
O003 C00H 1.427(3) . ?
O003 C00M 1.455(3) . ?
O005 C00F 1.215(4) . ?
N009 C00F 1.326(4) . ?
N00A C00N 1.350(4) . ?
N00A C00W 1.325(4) . ?
N00A C013 1.483(4) . ?
C00C C00D 1.471(4) . ?
C00C C00S 1.395(4) . ?
C00C C00T 1.408(4) . ?
C00D C00P 1.396(4) . ?
C00D C00Q 1.404(4) . ?
C00E C00H 1.503(4) . ?
C00E C00J 1.400(4) . ?
C00E C00L 1.382(4) . ?
C00F C00H 1.529(4) . ?
C00G C00I 1.406(4) . ?
C00G C00O 1.441(4) . ?
C00G C00V 1.427(4) . ?
C00H C00M 1.493(4) . ?
C00I C00K 1.402(4) . ?
C00I C00M 1.496(4) . ?
C00J C00P 1.377(4) . ?
C00K C00R 1.443(4) . ?
C00K C00U 1.444(4) . ?
C00L C00Q 1.386(4) . ?
C00N C00S 1.365(4) . ?
C00O C00Y 1.387(5) . ?
C00O C00Z 1.437(5) . ?
C00R C00Y 1.388(5) . ?
C00R C010 1.432(5) . ?
C00T C00W 1.373(4) . ?
C00U C011 1.352(5) . ?
C00V C00X 1.357(4) . ?
C00X C012 1.428(5) . ?
C00Z C012 1.339(6) . ?
C010 C014 1.357(6) . ?
C011 C014 1.417(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
F002 P001 F004 174.4(9) . . ?
F002 P001 F006 85.3(9) . . ?
F002 P001 F008 90.1(5) . . ?
F004 P001 F006 89.1(3) . . ?
F004 P001 F008 88.9(3) . . ?
F006 P001 F008 84.7(4) . . ?
F007 P001 F002 90.2(5) . . ?
F007 P001 F004 90.7(3) . . ?
F007 P001 F006 93.4(4) . . ?
F007 P001 F008 178.1(3) . . ?
F00B P001 F002 93.0(9) . . ?
F00B P001 F004 92.5(3) . . ?
F00B P001 F006 174.1(4) . . ?
F00B P001 F007 92.3(2) . . ?
F00B P001 F008 89.6(2) . . ?
F1 P001 F0 90.5(6) . . ?
F1 P001 F00C 88.2(4) . . ?
F1 P001 F4 172.9(17) . . ?
F00C P001 F0 86.2(4) . . ?
F2 P001 F0 177.2(5) . . ?
F2 P001 F1 92.3(6) . . ?
F2 P001 F00C 94.3(4) . . ?
F2 P001 F3 98.9(7) . . ?
F2 P001 F4 85.8(10) . . ?
F3 P001 F0 80.7(7) . . ?
F3 P001 F1 88.7(5) . . ?
F3 P001 F00C 166.5(7) . . ?
F3 P001 F4 98.4(17) . . ?
F4 P001 F0 91.5(10) . . ?
F4 P001 F00C 85.1(16) . . ?
C00H O003 C00M 62.40(16) . . ?
C00N N00A C013 120.2(3) . . ?
C00W N00A C00N 120.3(3) . . ?
C00W N00A C013 119.5(3) . . ?
C00S C00C C00D 122.8(2) . . ?
C00S C00C C00T 115.9(3) . . ?
C00T C00C C00D 121.3(3) . . ?
C00P C00D C00C 121.3(2) . . ?
C00P C00D C00Q 117.7(3) . . ?
C00Q C00D C00C 121.0(2) . . ?
C00J C00E C00H 119.3(2) . . ?
C00L C00E C00H 122.1(2) . . ?
C00L C00E C00J 118.6(3) . . ?
O005 C00F N009 124.5(3) . . ?
O005 C00F C00H 120.1(2) . . ?
N009 C00F C00H 115.3(2) . . ?
C00I C00G C00O 118.8(3) . . ?
C00I C00G C00V 123.0(3) . . ?
C00V C00G C00O 118.3(3) . . ?
O003 C00H C00E 114.7(2) . . ?
O003 C00H C00F 114.5(2) . . ?
O003 C00H C00M 59.71(16) . . ?
C00E C00H C00F 116.2(2) . . ?
C00M C00H C00E 120.9(2) . . ?
C00M C00H C00F 117.9(2) . . ?
C00G C00I C00M 119.4(3) . . ?
C00K C00I C00G 121.0(3) . . ?
C00K C00I C00M 119.6(3) . . ?
C00P C00J C00E 120.8(3) . . ?
C00I C00K C00R 119.1(3) . . ?
C00I C00K C00U 123.4(3) . . ?
C00R C00K C00U 117.5(3) . . ?
C00E C00L C00Q 120.7(3) . . ?
O003 C00M C00H 57.89(16) . . ?
O003 C00M C00I 115.9(2) . . ?
C00H C00M C00I 122.4(2) . . ?
N00A C00N C00S 120.4(3) . . ?
C00Y C00O C00G 119.8(3) . . ?
C00Y C00O C00Z 121.8(3) . . ?
C00Z C00O C00G 118.4(3) . . ?
C00J C00P C00D 121.1(3) . . ?
C00L C00Q C00D 121.0(3) . . ?
C00Y C00R C00K 119.4(3) . . ?
C00Y C00R C010 121.8(3) . . ?
C010 C00R C00K 118.8(3) . . ?
C00N C00S C00C 121.6(3) . . ?
C00W C00T C00C 120.2(3) . . ?
C011 C00U C00K 121.1(3) . . ?
C00X C00V C00G 121.0(3) . . ?
N00A C00W C00T 121.6(3) . . ?
C00V C00X C012 120.7(3) . . ?
C00O C00Y C00R 121.7(3) . . ?
C012 C00Z C00O 121.2(3) . . ?
C014 C010 C00R 121.1(3) . . ?
C00U C011 C014 121.1(3) . . ?
C00Z C012 C00X 120.5(3) . . ?
C010 C014 C011 120.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
