# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_20190520a_0m
_database_code_depnum_ccdc_archive 'CCDC 1917241'
loop_
_audit_author_name
_audit_author_address
chu
;IAS
China
;
_audit_update_record             
;
2019-05-20 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;
_audit_creation_date             2019-05-20
_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         'C26 H16 F5 O2 P'
_chemical_formula_sum            'C26 H16 F5 O2 P'
_chemical_formula_weight         486.36
_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'
P P 0.1023 0.0942 '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                   10.260(5)
_cell_length_b                   10.582(5)
_cell_length_c                   11.990(6)
_cell_angle_alpha                75.682(13)
_cell_angle_beta                 76.268(12)
_cell_angle_gamma                62.415(12)
_cell_volume                     1106.6(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9321
_cell_measurement_temperature    148.63
_cell_measurement_theta_max      23.01
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1251 before and 0.0764 after correction. The Ratio of minimum to maximum transmission is 0.8775. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            98394
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.200
_diffrn_ambient_temperature      148.63
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3413
_reflns_number_total             5047
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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         0.384
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5047
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      1.157
_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)+(0.0495P)²+1.1829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1804
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F004) \\sim Ueq, Uanis(F005) \\sim Ueq, Uanis(F006) \\sim Ueq,
Uanis(F007) \\sim Ueq, Uanis(F00E) \\sim Ueq, Uanis(C00X) \\sim Ueq,
Uanis(C00Y) \\sim Ueq, Uanis(C0AA) \\sim Ueq, Uanis(C00Z) \\sim Ueq, Uanis(F0)
\\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq,
Uanis(F00F) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 F004, F005, F006, F007, F00E, C00X, C00Y, C0AA, C00Z
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F004, F005, F006, F007, F00E, C00X, C00Y, C0AA, C00Z, F0, F1, F2, F3, F00F
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: F004(0.5) F005(0.5) F006(0.5) F007(0.5) F00E(0.5) C00X(0.5)
 C00Y(0.5) C0AA(0.5) C00Z(0.5) F0(0.5) F1(0.5) F2(0.5) F3(0.5) F00F(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W)
;
_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 0.37375(9) 0.30328(10) 0.15002(7) 0.0547(3) Uani 1 1 d . . . . .
O002 O 0.5498(2) 0.2185(2) 0.4398(2) 0.0634(6) Uani 1 1 d . . . . .
O003 O 0.5018(3) 0.2763(3) 0.0564(2) 0.0719(7) Uani 1 1 d . . . . .
F004 F 0.636(2) 0.013(2) 0.2336(18) 0.162(6) Uani 0.5 1 d . U P A 1
F005 F 0.8107(15) 0.1044(17) 0.2230(13) 0.104(4) Uani 0.5 1 d . U P A 1
F006 F 0.6400(17) -0.0751(16) 0.4312(12) 0.129(5) Uani 0.5 1 d . U P A 1
F007 F 0.8260(19) -0.0127(18) 0.4282(12) 0.114(4) Uani 0.5 1 d . U P A 1
C008 C 0.3424(3) 0.3975(3) 0.3728(2) 0.0480(7) Uani 1 1 d . . . . .
C009 C 0.4260(3) 0.3423(3) 0.4619(3) 0.0491(7) Uani 1 1 d . . . . .
C00A C 0.3018(3) 0.1705(3) 0.1786(3) 0.0528(7) Uani 1 1 d . . . . .
C00B C 0.3913(3) 0.4019(3) 0.5643(3) 0.0517(7) Uani 1 1 d . . . . .
C00C C 0.2236(4) 0.4764(4) 0.1195(2) 0.0529(7) Uani 1 1 d . . . . .
C00D C 0.2615(4) 0.5314(3) 0.5698(3) 0.0550(7) Uani 1 1 d . . . . .
F00E F 0.8420(12) -0.1669(11) 0.3292(11) 0.114(4) Uani 0.5 1 d . U P A 1
C00F C 0.4198(3) 0.2990(3) 0.2878(3) 0.0525(7) Uani 1 1 d . . . . .
C00G C 0.3333(4) 0.0907(4) 0.0920(3) 0.0624(8) Uani 1 1 d . . . . .
H00G H 0.388429 0.109748 0.019470 0.075 Uiso 1 1 calc R . . . .
C00H C 0.2589(4) 0.5924(4) 0.0721(3) 0.0622(9) Uani 1 1 d . . . . .
H00H H 0.359570 0.577874 0.058553 0.075 Uiso 1 1 calc R . . . .
C00I C 0.2191(4) 0.1431(4) 0.2832(3) 0.0655(9) Uani 1 1 d . . . . .
H00I H 0.196808 0.196626 0.343670 0.079 Uiso 1 1 calc R . . . .
C00J C 0.1746(4) 0.5909(4) 0.4772(3) 0.0644(9) Uani 1 1 d . . . . .
H00J H 0.087477 0.678978 0.482267 0.077 Uiso 1 1 calc R . . . .
C00K C 0.2112(4) 0.5268(4) 0.3813(3) 0.0601(8) Uani 1 1 d . . . . .
H00K H 0.149731 0.568343 0.321763 0.072 Uiso 1 1 calc R . . . .
C00L C 0.5419(4) 0.1958(4) 0.3339(3) 0.0640(9) Uani 1 1 d . . . . .
C00M C 0.0761(4) 0.4998(4) 0.1371(3) 0.0702(9) Uani 1 1 d . . . . .
H00M H 0.050512 0.421157 0.167912 0.084 Uiso 1 1 calc R . . . .
C00N C 0.2216(4) 0.5978(4) 0.6693(3) 0.0666(9) Uani 1 1 d . . . . .
H00N H 0.135731 0.686918 0.674497 0.080 Uiso 1 1 calc R . . . .
C00O C 0.4761(4) 0.3391(4) 0.6567(3) 0.0665(9) Uani 1 1 d . . . . .
H00O H 0.563665 0.251179 0.652616 0.080 Uiso 1 1 calc R . . . .
C00P C 0.2856(4) -0.0161(4) 0.1097(4) 0.0710(10) Uani 1 1 d . . . . .
H00P H 0.310127 -0.071815 0.050315 0.085 Uiso 1 1 calc R . . . .
C00Q C 0.1490(5) 0.7275(4) 0.0448(3) 0.0757(11) Uani 1 1 d . . . . .
H00Q H 0.173909 0.806300 0.012156 0.091 Uiso 1 1 calc R . . . .
C00R C 0.3052(5) 0.5353(5) 0.7575(3) 0.0736(10) Uani 1 1 d . . . . .
H00R H 0.276671 0.581256 0.823796 0.088 Uiso 1 1 calc R . . . .
C00S C 0.1687(4) 0.0380(4) 0.3000(3) 0.0734(10) Uani 1 1 d . . . . .
H00S H 0.110575 0.020489 0.371254 0.088 Uiso 1 1 calc R . . . .
C00T C 0.2032(4) -0.0414(4) 0.2125(4) 0.0734(10) Uani 1 1 d . . . . .
H00T H 0.169298 -0.113998 0.224246 0.088 Uiso 1 1 calc R . . . .
C00U C 0.4315(5) 0.4053(4) 0.7523(3) 0.0749(10) Uani 1 1 d . . . . .
H00U H 0.487231 0.362328 0.815546 0.090 Uiso 1 1 calc R . . . .
C00V C 0.0032(5) 0.7500(4) 0.0642(4) 0.0845(12) Uani 1 1 d . . . . .
H00V H -0.072490 0.844364 0.045707 0.101 Uiso 1 1 calc R . . . .
C00W C -0.0335(5) 0.6365(5) 0.1102(4) 0.0889(13) Uani 1 1 d . . . . .
H00W H -0.134552 0.652142 0.123394 0.107 Uiso 1 1 calc R . . . .
C00X C 0.6782(8) 0.0760(8) 0.2791(5) 0.0431(14) Uani 0.5 1 d . U P A 1
C00Y C 0.7564(8) -0.0507(7) 0.3755(6) 0.0608(16) Uani 0.5 1 d . U P A 1
C0AA C 0.6500(13) 0.0392(13) 0.3244(10) 0.088(3) Uani 0.5 1 d . U P A 2
C00Z C 0.7990(12) 0.0115(14) 0.3169(10) 0.103(3) Uani 0.5 1 d . U P A 2
F0 F 0.6206(16) 0.0029(15) 0.2253(11) 0.089(2) Uani 0.5 1 d . U P A 2
F1 F 0.6771(17) -0.0862(18) 0.4586(11) 0.096(3) Uani 0.5 1 d . U P A 2
F2 F 0.8370(16) 0.0301(18) 0.4036(15) 0.115(4) Uani 0.5 1 d . U P A 2
F3 F 0.7688(14) 0.1064(18) 0.2030(12) 0.107(3) Uani 0.5 1 d . U P A 2
F00F F 0.8899(11) -0.1359(13) 0.3041(12) 0.109(3) Uani 0.5 1 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 O003 1.476(2) . ?
P001 C00A 1.799(3) . ?
P001 C00C 1.785(4) . ?
P001 C00F 1.808(3) . ?
O002 C009 1.368(3) . ?
O002 C00L 1.376(4) . ?
F004 C00X 1.223(17) . ?
F005 C00X 1.495(13) . ?
F006 C00Y 1.327(17) . ?
F007 C00Y 1.296(16) . ?
C008 C009 1.373(4) . ?
C008 C00F 1.459(4) . ?
C008 C00K 1.412(4) . ?
C009 C00B 1.413(4) . ?
C00A C00G 1.385(4) . ?
C00A C00I 1.386(4) . ?
C00B C00D 1.403(4) . ?
C00B C00O 1.409(4) . ?
C00C C00H 1.389(4) . ?
C00C C00M 1.387(5) . ?
C00D C00J 1.424(5) . ?
C00D C00N 1.415(4) . ?
F00E C00Y 1.303(13) . ?
C00F C00L 1.354(5) . ?
C00G C00P 1.381(5) . ?
C00H C00Q 1.369(5) . ?
C00I C00S 1.385(5) . ?
C00J C00K 1.366(4) . ?
C00L C00X 1.525(7) . ?
C00L C0AA 1.523(12) . ?
C00M C00W 1.377(5) . ?
C00N C00R 1.361(5) . ?
C00O C00U 1.366(5) . ?
C00P C00T 1.363(5) . ?
C00Q C00V 1.372(6) . ?
C00R C00U 1.388(6) . ?
C00S C00T 1.384(5) . ?
C00V C00W 1.372(6) . ?
C00X C00Y 1.567(10) . ?
C0AA C00Z 1.402(16) . ?
C0AA F0 1.468(15) . ?
C0AA F1 1.800(17) . ?
C0AA F3 1.887(18) . ?
C00Z F2 1.279(17) . ?
C00Z F3 1.48(2) . ?
C00Z F00F 1.424(16) . ?

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
O003 P001 C00A 113.09(14) . . ?
O003 P001 C00C 112.43(16) . . ?
O003 P001 C00F 112.58(15) . . ?
C00A P001 C00F 104.96(14) . . ?
C00C P001 C00A 107.48(15) . . ?
C00C P001 C00F 105.72(14) . . ?
C009 O002 C00L 105.6(2) . . ?
C009 C008 C00F 106.3(3) . . ?
C009 C008 C00K 118.0(3) . . ?
C00K C008 C00F 135.7(3) . . ?
O002 C009 C008 110.8(2) . . ?
O002 C009 C00B 123.4(3) . . ?
C008 C009 C00B 125.8(3) . . ?
C00G C00A P001 118.0(3) . . ?
C00G C00A C00I 118.8(3) . . ?
C00I C00A P001 123.2(2) . . ?
C00D C00B C009 115.0(3) . . ?
C00D C00B C00O 120.6(3) . . ?
C00O C00B C009 124.4(3) . . ?
C00H C00C P001 117.3(3) . . ?
C00M C00C P001 123.8(3) . . ?
C00M C00C C00H 118.9(3) . . ?
C00B C00D C00J 119.8(3) . . ?
C00B C00D C00N 117.8(3) . . ?
C00N C00D C00J 122.3(3) . . ?
C008 C00F P001 130.8(2) . . ?
C00L C00F P001 124.6(2) . . ?
C00L C00F C008 104.6(3) . . ?
C00P C00G C00A 120.9(3) . . ?
C00Q C00H C00C 120.1(3) . . ?
C00S C00I C00A 120.2(3) . . ?
C00K C00J C00D 122.8(3) . . ?
C00J C00K C008 118.5(3) . . ?
O002 C00L C00X 116.7(4) . . ?
O002 C00L C0AA 106.2(5) . . ?
C00F C00L O002 112.7(3) . . ?
C00F C00L C00X 129.9(4) . . ?
C00F C00L C0AA 137.9(5) . . ?
C00W C00M C00C 120.4(3) . . ?
C00R C00N C00D 120.6(3) . . ?
C00U C00O C00B 119.6(4) . . ?
C00T C00P C00G 119.8(3) . . ?
C00H C00Q C00V 120.5(4) . . ?
C00N C00R C00U 121.1(3) . . ?
C00T C00S C00I 119.8(4) . . ?
C00P C00T C00S 120.4(3) . . ?
C00O C00U C00R 120.3(3) . . ?
C00Q C00V C00W 120.1(4) . . ?
C00V C00W C00M 120.0(4) . . ?
F004 C00X F005 121.0(12) . . ?
F004 C00X C00L 108.2(11) . . ?
F004 C00X C00Y 98.9(12) . . ?
F005 C00X C00L 118.5(8) . . ?
F005 C00X C00Y 96.6(8) . . ?
C00L C00X C00Y 110.5(5) . . ?
F006 C00Y C00X 98.6(8) . . ?
F007 C00Y F006 120.9(11) . . ?
F007 C00Y F00E 113.4(11) . . ?
F007 C00Y C00X 109.9(9) . . ?
F00E C00Y F006 103.3(10) . . ?
F00E C00Y C00X 109.4(8) . . ?
C00L C0AA F1 116.5(9) . . ?
C00L C0AA F3 88.6(8) . . ?
C00Z C0AA C00L 113.4(10) . . ?
C00Z C0AA F0 113.0(10) . . ?
C00Z C0AA F1 85.8(10) . . ?
C00Z C0AA F3 51.1(8) . . ?
F0 C0AA C00L 107.3(9) . . ?
F0 C0AA F1 119.7(11) . . ?
F0 C0AA F3 80.4(8) . . ?
F1 C0AA F3 136.7(9) . . ?
C0AA C00Z F3 81.6(9) . . ?
C0AA C00Z F00F 108.6(11) . . ?
F2 C00Z C0AA 117.2(12) . . ?
F2 C00Z F3 129.2(14) . . ?
F2 C00Z F00F 105.7(12) . . ?
F00F C00Z F3 111.9(11) . . ?
C00Z F3 C0AA 47.3(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
