# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ZRY01-sad
_database_code_depnum_ccdc_archive 'CCDC 1986367'
loop_
_audit_author_name
_audit_author_address
Luqing-ZRY
;The Cambridge Crystallographic Data Center
China
;
_audit_update_record             
;
2020-02-26 deposited with the CCDC.	2020-04-30 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            'C17 H17 F6 N2 P'
_chemical_formula_weight         394.29

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'
N N 0.0311 0.0180 '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'
P P 0.2955 0.4335 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.8004(9)
_cell_length_b                   11.9948(15)
_cell_length_c                   21.500(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.373(4)
_cell_angle_gamma                90
_cell_volume                     1746.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9590
_cell_measurement_theta_min      4.13
_cell_measurement_theta_max      74.57

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    2.005
_shelx_estimated_absorpt_T_min   0.501
_shelx_estimated_absorpt_T_max   0.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.501
_exptl_absorpt_correction_T_max  0.585
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker, 2005)'
_exptl_absorpt_special_details   
;
about 2 hours for data collection, 
with scale.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            24274
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.131
_diffrn_reflns_theta_max         74.619
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3487
_reflns_number_gt                3291
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1159P)²+3.0033P] 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         3487
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.2315
_refine_ls_wR_factor_gt          0.2292
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_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
P1 P 0.64661(15) 0.26856(8) 0.17043(4) 0.0475(3) Uani 1 1 d . . . . .
F1 F 0.5376(4) 0.1667(2) 0.13538(11) 0.0634(7) Uani 1 1 d . . . . .
F2 F 0.8432(5) 0.2326(3) 0.1430(2) 0.1169(15) Uani 1 1 d . . . . .
F3 F 0.7015(7) 0.1896(2) 0.22895(14) 0.1057(14) Uani 1 1 d . . . . .
F4 F 0.5940(7) 0.3473(3) 0.11385(13) 0.1097(14) Uani 1 1 d . . . . .
F5 F 0.7539(5) 0.3705(2) 0.20739(11) 0.0717(8) Uani 1 1 d . . . . .
F6 F 0.4563(5) 0.3027(3) 0.20150(19) 0.1020(12) Uani 1 1 d . . . . .
N1 N 0.8742(4) 0.8249(2) 0.64652(13) 0.0353(6) Uani 1 1 d . . . . .
N2 N 0.6519(4) 0.3365(2) 0.34547(12) 0.0389(6) Uani 1 1 d . . . . .
H2 H 0.6328 0.3215 0.3053 0.047 Uiso 1 1 calc R U . . .
C1 C 0.7620(9) 0.9544(5) 0.7248(3) 0.114(3) Uani 1 1 d . . . . .
H1C H 0.6441 0.9757 0.6977 0.171 Uiso 1 1 calc R U . . .
H1B H 0.8052 1.0175 0.7517 0.171 Uiso 1 1 calc R U . . .
H1A H 0.7309 0.8908 0.7508 0.171 Uiso 1 1 calc R U . . .
C2 C 0.9172(6) 0.9240(3) 0.6871(2) 0.0567(10) Uani 1 1 d . . . . .
H2A H 1.0386 0.9092 0.7150 0.068 Uiso 1 1 calc R U . . .
H2B H 0.9444 0.9883 0.6603 0.068 Uiso 1 1 calc R U . . .
C3 C 0.8788(5) 0.7209(3) 0.67082(15) 0.0369(7) Uani 1 1 d . . . . .
H3 H 0.9041 0.7115 0.7147 0.044 Uiso 1 1 calc R U . . .
C4 C 0.8481(5) 0.6296(3) 0.63386(15) 0.0387(7) Uani 1 1 d . . . . .
H4 H 0.8545 0.5577 0.6525 0.046 Uiso 1 1 calc R U . . .
C5 C 0.8080(4) 0.6385(3) 0.57004(15) 0.0361(7) Uani 1 1 d . . . . .
C8 C 0.7763(4) 0.5353(3) 0.53334(15) 0.0371(7) Uani 1 1 d . . . . .
H8 H 0.7899 0.4663 0.5550 0.045 Uiso 1 1 calc R U . . .
C9 C 0.7303(4) 0.5322(3) 0.47240(15) 0.0368(7) Uani 1 1 d . . . . .
H9 H 0.7159 0.6018 0.4513 0.044 Uiso 1 1 calc R U . . .
C11 C 0.7000(4) 0.4333(2) 0.43476(14) 0.0331(6) Uani 1 1 d . . . . .
C12 C 0.6954(4) 0.3154(2) 0.45018(13) 0.0307(6) Uani 1 1 d . . . . .
C13 C 0.7106(5) 0.2542(3) 0.50531(15) 0.0388(7) Uani 1 1 d . . . . .
H13 H 0.7293 0.2905 0.5447 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6978(6) 0.1387(3) 0.50166(19) 0.0500(9) Uani 1 1 d . . . . .
H14 H 0.7062 0.0963 0.5391 0.060 Uiso 1 1 calc R U . . .
C15 C 0.6730(5) 0.0838(3) 0.4446(2) 0.0520(9) Uani 1 1 d . . . . .
H15 H 0.6676 0.0047 0.4439 0.062 Uiso 1 1 calc R U . . .
C10 C 0.6721(5) 0.4401(3) 0.37064(15) 0.0392(7) Uani 1 1 d . . . . .
H10 H 0.6676 0.5075 0.3474 0.047 Uiso 1 1 calc R U . . .
C17 C 0.6662(4) 0.2585(3) 0.39282(14) 0.0328(6) Uani 1 1 d . . . . .
C16 C 0.6560(4) 0.1421(3) 0.38872(18) 0.0430(8) Uani 1 1 d . . . . .
H16 H 0.6383 0.1050 0.3496 0.052 Uiso 1 1 calc R U . . .
C6 C 0.8033(4) 0.7462(3) 0.54492(15) 0.0400(7) Uani 1 1 d . . . . .
H6 H 0.7764 0.7566 0.5012 0.048 Uiso 1 1 calc R U . . .
C7 C 0.8376(4) 0.8373(3) 0.58369(17) 0.0407(7) Uani 1 1 d . . . . .
H7 H 0.8357 0.9100 0.5661 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F4 1.555(3) . ?
P1 F6 1.566(3) . ?
P1 F2 1.572(4) . ?
P1 F1 1.583(2) . ?
P1 F3 1.591(3) . ?
P1 F5 1.597(2) . ?
N1 C3 1.351(4) . ?
N1 C7 1.359(4) . ?
N1 C2 1.488(4) . ?
N2 C10 1.357(4) . ?
N2 C17 1.380(4) . ?
N2 H2 0.8800 . ?
C1 C2 1.437(6) . ?
C1 H1C 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1A 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.358(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(5) . ?
C5 C8 1.473(4) . ?
C8 C9 1.319(5) . ?
C8 H8 0.9500 . ?
C9 C11 1.440(4) . ?
C9 H9 0.9500 . ?
C11 C10 1.376(4) . ?
C11 C12 1.453(4) . ?
C12 C13 1.390(4) . ?
C12 C17 1.407(4) . ?
C13 C14 1.389(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(6) . ?
C15 H15 0.9500 . ?
C10 H10 0.9500 . ?
C17 C16 1.400(4) . ?
C16 H16 0.9500 . ?
C6 C7 1.382(5) . ?
C6 H6 0.9500 . ?
C7 H7 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
F4 P1 F6 92.1(2) . . ?
F4 P1 F2 90.8(3) . . ?
F6 P1 F2 176.8(2) . . ?
F4 P1 F1 91.90(15) . . ?
F6 P1 F1 92.06(18) . . ?
F2 P1 F1 89.23(16) . . ?
F4 P1 F3 179.13(17) . . ?
F6 P1 F3 87.7(2) . . ?
F2 P1 F3 89.4(3) . . ?
F1 P1 F3 88.96(15) . . ?
F4 P1 F5 89.16(16) . . ?
F6 P1 F5 86.84(18) . . ?
F2 P1 F5 91.81(17) . . ?
F1 P1 F5 178.50(15) . . ?
F3 P1 F5 89.98(15) . . ?
C3 N1 C7 118.8(3) . . ?
C3 N1 C2 121.0(3) . . ?
C7 N1 C2 120.2(3) . . ?
C10 N2 C17 109.2(3) . . ?
C10 N2 H2 125.4 . . ?
C17 N2 H2 125.4 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1C C1 H1B 109.5 . . ?
C2 C1 H1A 109.5 . . ?
H1C C1 H1A 109.5 . . ?
H1B C1 H1A 109.5 . . ?
C1 C2 N1 114.8(3) . . ?
C1 C2 H2A 108.6 . . ?
N1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
N1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.5 . . ?
N1 C3 C4 121.4(3) . . ?
N1 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 116.8(3) . . ?
C4 C5 C8 118.3(3) . . ?
C6 C5 C8 124.9(3) . . ?
C9 C8 C5 124.4(3) . . ?
C9 C8 H8 117.8 . . ?
C5 C8 H8 117.8 . . ?
C8 C9 C11 126.1(3) . . ?
C8 C9 H9 116.9 . . ?
C11 C9 H9 116.9 . . ?
C10 C11 C9 120.9(3) . . ?
C10 C11 C12 106.4(3) . . ?
C9 C11 C12 132.7(3) . . ?
C13 C12 C17 119.0(3) . . ?
C13 C12 C11 135.0(3) . . ?
C17 C12 C11 106.0(3) . . ?
C14 C13 C12 118.6(3) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C13 121.7(3) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
N2 C10 C11 110.1(3) . . ?
N2 C10 H10 124.9 . . ?
C11 C10 H10 124.9 . . ?
N2 C17 C16 129.1(3) . . ?
N2 C17 C12 108.2(3) . . ?
C16 C17 C12 122.7(3) . . ?
C15 C16 C17 116.7(3) . . ?
C15 C16 H16 121.7 . . ?
C17 C16 H16 121.7 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
N1 C7 C6 121.2(3) . . ?
N1 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?

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
C3 N1 C2 C1 -74.5(6) . . . . ?
C7 N1 C2 C1 108.4(5) . . . . ?
C7 N1 C3 C4 0.1(4) . . . . ?
C2 N1 C3 C4 -177.1(3) . . . . ?
N1 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C3 C4 C5 C8 -179.9(3) . . . . ?
C4 C5 C8 C9 177.6(3) . . . . ?
C6 C5 C8 C9 -3.3(5) . . . . ?
C5 C8 C9 C11 179.4(3) . . . . ?
C8 C9 C11 C10 -173.4(3) . . . . ?
C8 C9 C11 C12 5.0(5) . . . . ?
C10 C11 C12 C13 -178.7(3) . . . . ?
C9 C11 C12 C13 2.7(6) . . . . ?
C10 C11 C12 C17 0.6(3) . . . . ?
C9 C11 C12 C17 -178.0(3) . . . . ?
C17 C12 C13 C14 0.5(4) . . . . ?
C11 C12 C13 C14 179.6(3) . . . . ?
C12 C13 C14 C15 0.9(5) . . . . ?
C13 C14 C15 C16 -1.3(5) . . . . ?
C17 N2 C10 C11 0.0(3) . . . . ?
C9 C11 C10 N2 178.4(3) . . . . ?
C12 C11 C10 N2 -0.4(3) . . . . ?
C10 N2 C17 C16 -179.4(3) . . . . ?
C10 N2 C17 C12 0.4(3) . . . . ?
C13 C12 C17 N2 178.8(3) . . . . ?
C11 C12 C17 N2 -0.6(3) . . . . ?
C13 C12 C17 C16 -1.4(4) . . . . ?
C11 C12 C17 C16 179.2(3) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
N2 C17 C16 C15 -179.3(3) . . . . ?
C12 C17 C16 C15 1.0(4) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C8 C5 C6 C7 -179.2(3) . . . . ?
C3 N1 C7 C6 0.8(4) . . . . ?
C2 N1 C7 C6 178.0(3) . . . . ?
C5 C6 C7 N1 -0.8(4) . . . . ?

_refine_diff_density_max         0.883
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.077

