# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_d8v18488
_database_code_depnum_ccdc_archive 'CCDC 1911058'
loop_
_audit_author_name
_audit_author_address
'Xuebing Leng'
;Shanghai institute of Organic Chemistry
China
;
_audit_update_record             
;
2019-04-18 deposited with the CCDC.	2019-05-21 downloaded from the CCDC.
;
_audit_creation_date             2018-06-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C2 Cu F6, C24 H20 P'
_chemical_formula_sum            'C26 H20 Cu F6 P'
_chemical_formula_weight         540.93
_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'
Cu Cu 0.3201 1.2651 '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'

_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.5529(6)
_cell_length_b                   7.3629(3)
_cell_length_c                   19.8862(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2277.26(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5195
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    1.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0735 before and 0.0504 after correction. The Ratio of minimum to maximum transmission is 0.8576. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12640
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.431
_diffrn_ambient_temperature      170.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2132
_reflns_number_total             2612
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.959
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.114
_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     156
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0459
_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)+(0.0873P)²+1.7865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1500
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed U12: P1(0)
 Fixed U23: P1(0)
 Fixed Uiso: H3(0.035) H4(0.04) H5(0.04) H6(0.04) H7(0.035) H9(0.036)
 H10(0.043) H11(0.046) H12(0.046) H13(0.037)
 Fixed X: Cu1(0.5) P1(0.5) H3(0.5471) H4(0.4752) H5(0.3273) H6(0.2517)
 H7(0.3234) H9(0.4049) H10(0.313) H11(0.2797) H12(0.3376) H13(0.4295)
 Fixed Y: Cu1(0.5) H3(0.7626) H4(0.9528) H5(0.9177) H6(0.6933) H7(0.4979)
 H9(0.1529) H10(-0.0467) H11(-0.0005) H12(0.2473) H13(0.4479)
 Fixed Z: Cu1(0.5) P1(0.75) H3(0.6675) H4(0.5921) H5(0.575) H6(0.6326)
 H7(0.7057) H9(0.7132) H10(0.7694) H11(0.8824) H12(0.9399) H13(0.8848)
;
_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
Cu1 Cu 0.5000 0.5000 0.5000 0.0333(2) Uani 1 2 d S T P . .
F1 F 0.39141(12) 0.2817(3) 0.57907(9) 0.0473(5) Uani 1 1 d . . . . .
F2 F 0.39207(17) 0.1978(4) 0.47650(14) 0.0853(10) Uani 1 1 d . . . . .
F3 F 0.32093(14) 0.4333(4) 0.50585(11) 0.0634(6) Uani 1 1 d . . . . .
C1 C 0.40013(19) 0.3496(4) 0.51462(14) 0.0370(6) Uani 1 1 d . . . . .
P1 P 0.5000 0.46619(13) 0.7500 0.0206(2) Uani 1 2 d S T P . .
C2 C 0.44238(15) 0.6109(3) 0.69328(11) 0.0224(5) Uani 1 1 d . . . . .
C3 C 0.48723(16) 0.7473(4) 0.65985(14) 0.0293(6) Uani 1 1 d . . . . .
H3 H 0.5471 0.7626 0.6675 0.035 Uiso 1 1 calc R . . . .
C4 C 0.44452(19) 0.8608(4) 0.61548(13) 0.0330(6) Uani 1 1 d . . . . .
H4 H 0.4752 0.9528 0.5921 0.040 Uiso 1 1 calc R . . . .
C5 C 0.35667(18) 0.8398(4) 0.60534(14) 0.0336(6) Uani 1 1 d . . . . .
H5 H 0.3273 0.9177 0.5750 0.040 Uiso 1 1 calc R . . . .
C6 C 0.31192(17) 0.7060(4) 0.63927(14) 0.0333(6) Uani 1 1 d . . . . .
H6 H 0.2517 0.6933 0.6326 0.040 Uiso 1 1 calc R . . . .
C7 C 0.35424(16) 0.5907(4) 0.68288(13) 0.0288(5) Uani 1 1 d . . . . .
H7 H 0.3234 0.4979 0.7057 0.035 Uiso 1 1 calc R . . . .
C8 C 0.42681(15) 0.3196(3) 0.79418(12) 0.0234(5) Uani 1 1 d . . . . .
C9 C 0.39149(18) 0.1719(4) 0.75927(14) 0.0301(6) Uani 1 1 d . . . . .
H9 H 0.4049 0.1529 0.7132 0.036 Uiso 1 1 calc R . . . .
C10 C 0.33699(17) 0.0540(4) 0.79271(16) 0.0358(6) Uani 1 1 d . . . . .
H10 H 0.3130 -0.0467 0.7694 0.043 Uiso 1 1 calc R . . . .
C11 C 0.31706(18) 0.0815(4) 0.85979(16) 0.0382(7) Uani 1 1 d . . . . .
H11 H 0.2797 -0.0005 0.8824 0.046 Uiso 1 1 calc R . . . .
C12 C 0.35149(19) 0.2283(4) 0.89396(15) 0.0384(7) Uani 1 1 d . . . . .
H12 H 0.3376 0.2473 0.9399 0.046 Uiso 1 1 calc R . . . .
C13 C 0.40607(17) 0.3471(4) 0.86127(14) 0.0311(6) Uani 1 1 d . . . . .
H13 H 0.4295 0.4479 0.8848 0.037 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0316(3) 0.0407(3) 0.0275(3) 0.00540(19) 0.00098(17) -0.0112(2)
F1 0.0524(11) 0.0463(10) 0.0433(10) 0.0120(8) 0.0113(8) -0.0108(9)
F2 0.0864(17) 0.0884(18) 0.0813(16) -0.0536(15) 0.0447(14) -0.0517(15)
F3 0.0326(11) 0.0814(16) 0.0763(15) 0.0256(12) -0.0056(9) -0.0089(11)
C1 0.0388(16) 0.0412(16) 0.0310(13) -0.0003(12) 0.0046(11) -0.0105(13)
P1 0.0189(5) 0.0217(4) 0.0211(5) 0.000 -0.0014(3) 0.000
C2 0.0221(11) 0.0216(11) 0.0236(11) -0.0027(9) -0.0041(9) 0.0022(9)
C3 0.0242(12) 0.0295(13) 0.0341(14) 0.0017(11) -0.0010(10) -0.0002(10)
C4 0.0386(15) 0.0277(13) 0.0328(13) 0.0036(10) 0.0013(11) 0.0045(11)
C5 0.0398(15) 0.0299(13) 0.0310(13) -0.0015(11) -0.0090(11) 0.0120(12)
C6 0.0239(13) 0.0345(14) 0.0416(14) -0.0069(12) -0.0100(11) 0.0078(11)
C7 0.0240(12) 0.0287(13) 0.0337(13) -0.0016(11) -0.0014(10) 0.0018(10)
C8 0.0225(11) 0.0221(11) 0.0257(11) 0.0011(9) -0.0020(9) -0.0006(9)
C9 0.0301(13) 0.0271(13) 0.0332(13) -0.0029(10) -0.0029(10) -0.0018(11)
C10 0.0285(14) 0.0271(13) 0.0517(17) 0.0014(12) -0.0089(12) -0.0053(11)
C11 0.0301(14) 0.0326(14) 0.0519(17) 0.0136(13) 0.0010(13) -0.0053(11)
C12 0.0405(16) 0.0429(16) 0.0319(14) 0.0069(12) 0.0049(12) -0.0048(13)
C13 0.0355(14) 0.0302(13) 0.0276(12) 0.0002(10) -0.0007(11) -0.0045(11)

_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
Cu1 C1 1.930(3) 5_666 ?
Cu1 C1 1.930(3) . ?
F1 C1 1.382(3) . ?
F2 C1 1.356(4) . ?
F3 C1 1.388(4) . ?
P1 C2 1.792(2) . ?
P1 C2 1.792(2) 3_656 ?
P1 C8 1.798(2) . ?
P1 C8 1.798(2) 3_656 ?
C2 C3 1.392(4) . ?
C2 C7 1.394(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.403(3) . ?
C8 C13 1.387(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(4) . ?
C13 H13 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
C1 Cu1 C1 180.0 5_666 . ?
F1 C1 Cu1 115.2(2) . . ?
F1 C1 F3 100.9(2) . . ?
F2 C1 Cu1 117.6(2) . . ?
F2 C1 F1 102.2(3) . . ?
F2 C1 F3 102.3(3) . . ?
F3 C1 Cu1 116.1(2) . . ?
C2 P1 C2 107.03(15) 3_656 . ?
C2 P1 C8 111.47(10) . 3_656 ?
C2 P1 C8 110.36(11) . . ?
C2 P1 C8 110.36(11) 3_656 3_656 ?
C2 P1 C8 111.47(10) 3_656 . ?
C8 P1 C8 106.22(16) 3_656 . ?
C3 C2 P1 118.63(18) . . ?
C3 C2 C7 119.9(2) . . ?
C7 C2 P1 121.44(19) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 120.1 . . ?
C6 C7 C2 119.7(2) . . ?
C6 C7 H7 120.1 . . ?
C9 C8 P1 118.14(19) . . ?
C13 C8 P1 121.98(19) . . ?
C13 C8 C9 119.9(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.2(3) . . ?
C12 C13 H13 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
