# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_DOT(SMALL)1137
_audit_block_doi                 10.5517/ccdc.csd.cc2j234w
_database_code_depnum_ccdc_archive 'CCDC 2325717'
loop_
_audit_author_name
_audit_author_address
'GAVIN CHIT TSUI'
;Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2024-01-16 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 Cu F10 P'
_chemical_formula_weight         640.95

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   18.025(4)
_cell_length_b                   7.2972(18)
_cell_length_c                   22.077(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.088(6)
_cell_angle_gamma                90
_cell_volume                     2690.8(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    330
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.957
_shelx_estimated_absorpt_T_min   0.701
_shelx_estimated_absorpt_T_max   0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6265
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15426
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.439
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2432
_reflns_number_gt                1483
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1593P)²+5.5800P] 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         2432
_refine_ls_number_parameters     202
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0898
_refine_ls_wR_factor_ref         0.2839
_refine_ls_wR_factor_gt          0.2473
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.067
_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
Cu1 Cu 0.750000 0.750000 1.000000 0.1363(10) Uani 1 2 d S . P . .
P1 P 0.500000 0.8157(3) 0.750000 0.0384(6) Uani 1 2 d S T P . .
C1 C 0.5855(3) 0.9620(8) 0.7663(3) 0.0444(14) Uani 1 1 d . . . . .
C2 C 0.6517(3) 0.9469(9) 0.8239(3) 0.0567(16) Uani 1 1 d . . . . .
H2A H 0.653194 0.860070 0.855149 0.068 Uiso 1 1 calc R U . . .
C3 C 0.7167(4) 1.0654(11) 0.8340(4) 0.075(2) Uani 1 1 d . . . . .
H3A H 0.762028 1.057227 0.872238 0.090 Uiso 1 1 calc R U . . .
C4 C 0.7129(4) 1.1937(11) 0.7872(4) 0.078(2) Uani 1 1 d . . . . .
H4A H 0.755670 1.273209 0.794268 0.093 Uiso 1 1 calc R U . . .
C5 C 0.6469(4) 1.2052(9) 0.7305(4) 0.073(2) Uani 1 1 d . . . . .
H5A H 0.645400 1.291207 0.698986 0.087 Uiso 1 1 calc R U . . .
C6 C 0.5836(4) 1.0920(9) 0.7199(3) 0.0604(17) Uani 1 1 d . . . . .
H6A H 0.538696 1.101554 0.681428 0.072 Uiso 1 1 calc R U . . .
C7 C 0.4888(3) 0.6685(8) 0.6823(3) 0.0422(13) Uani 1 1 d . . . . .
C8 C 0.5390(3) 0.6772(9) 0.6482(3) 0.0493(14) Uani 1 1 d . . . . .
H8A H 0.579115 0.765608 0.659210 0.059 Uiso 1 1 calc R U . . .
C9 C 0.5305(4) 0.5582(10) 0.5989(3) 0.0647(18) Uani 1 1 d . . . . .
H9A H 0.564948 0.564623 0.576409 0.078 Uiso 1 1 calc R U . . .
C10 C 0.4704(5) 0.4265(9) 0.5819(3) 0.0649(18) Uani 1 1 d . . . . .
H10A H 0.464472 0.345118 0.548031 0.078 Uiso 1 1 calc R U . . .
C11 C 0.4203(4) 0.4169(9) 0.6149(3) 0.0655(18) Uani 1 1 d . . . . .
H11A H 0.379439 0.330243 0.603053 0.079 Uiso 1 1 calc R U . . .
C12 C 0.4298(3) 0.5350(9) 0.6659(3) 0.0538(15) Uani 1 1 d . . . . .
H12A H 0.396606 0.525253 0.689392 0.065 Uiso 1 1 calc R U . . .
C13 C 0.8109(10) 0.664(2) 0.9508(9) 0.071(7) Uani 0.46(3) 1 d D U P A 1
C14 C 0.8613(12) 0.494(3) 0.9807(10) 0.092(8) Uani 0.46(3) 1 d D U P A 1
C13' C 0.869(2) 0.629(6) 0.986(2) 0.203(16) Uani 0.54(3) 1 d D U P A 3
C14' C 0.796(2) 0.510(6) 0.9505(19) 0.196(15) Uani 0.54(3) 1 d D U P A 3
F1 F 0.7690(3) 0.5817(10) 0.8860(2) 0.126(2) Uani 1 1 d . . . . .
F2 F 0.8776(4) 0.7677(8) 0.9532(4) 0.148(3) Uani 1 1 d . . . . .
F3 F 0.7987(5) 0.3587(9) 0.9761(4) 0.160(3) Uani 1 1 d . . . . .
F4 F 0.8988(5) 0.4361(10) 0.9422(4) 0.167(3) Uani 1 1 d . . . . .
F5 F 0.9072(3) 0.5409(9) 1.0436(2) 0.121(2) 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
Cu1 C13 1.918(15) . ?
Cu1 C13 1.918(15) 7_667 ?
Cu1 C14' 2.37(4) . ?
Cu1 C14' 2.37(4) 7_667 ?
Cu1 C13' 2.44(4) 7_667 ?
Cu1 C13' 2.44(4) . ?
P1 C7 1.789(6) . ?
P1 C7 1.789(6) 2_656 ?
P1 C1 1.796(6) 2_656 ?
P1 C1 1.796(6) . ?
C1 C2 1.382(8) . ?
C1 C6 1.387(8) . ?
C2 C3 1.404(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(11) . ?
C3 H3A 0.9300 . ?
C4 C5 1.368(10) . ?
C4 H4A 0.9300 . ?
C5 C6 1.356(9) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.379(8) . ?
C7 C12 1.387(8) . ?
C8 C9 1.356(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.390(10) . ?
C9 H9A 0.9300 . ?
C10 C11 1.359(10) . ?
C10 H10A 0.9300 . ?
C11 C12 1.376(9) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 F2 1.404(18) . ?
C13 F1 1.472(19) . ?
C13 C14 1.529(10) . ?
C14 F4 1.34(2) . ?
C14 F5 1.36(2) . ?
C14 F3 1.48(2) . ?
C13' F5 1.35(5) . ?
C13' F2 1.29(5) . ?
C13' C14' 1.526(10) . ?
C14' F1 1.42(4) . ?
C14' F3 1.23(4) . ?
C14' F4 2.01(4) . ?

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
C13 Cu1 C13 179.999(11) . 7_667 ?
C13 Cu1 C14' 151.1(10) . 7_667 ?
C13 Cu1 C14' 28.9(10) 7_667 7_667 ?
C14' Cu1 C14' 179.999(19) . 7_667 ?
C13 Cu1 C13' 154.9(10) . 7_667 ?
C13 Cu1 C13' 25.1(10) 7_667 7_667 ?
C14' Cu1 C13' 37.0(5) . . ?
C14' Cu1 C13' 143.0(5) 7_667 . ?
C13' Cu1 C13' 180.000(18) 7_667 . ?
C7 P1 C7 106.2(4) . 2_656 ?
C7 P1 C1 111.8(2) . 2_656 ?
C7 P1 C1 110.1(2) 2_656 2_656 ?
C7 P1 C1 110.1(2) . . ?
C7 P1 C1 111.8(2) 2_656 . ?
C1 P1 C1 107.1(4) 2_656 . ?
C2 C1 C6 120.4(5) . . ?
C2 C1 P1 121.1(4) . . ?
C6 C1 P1 118.5(4) . . ?
C1 C2 C3 118.5(6) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 H2A 120.7 . . ?
C4 C3 C2 119.7(7) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C5 C4 C3 120.6(6) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C6 C5 C4 120.4(7) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C1 120.3(6) . . ?
C5 C6 H6A 119.9 . . ?
C1 C6 H6A 119.9 . . ?
C8 C7 C12 119.1(5) . . ?
C8 C7 P1 122.5(4) . . ?
C12 C7 P1 118.3(4) . . ?
C9 C8 C7 120.6(6) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C8 C9 C10 120.0(6) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C11 C10 C9 120.0(6) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C10 C11 C12 120.1(6) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C11 C12 C7 120.1(6) . . ?
C11 C12 H12A 120.0 . . ?
C7 C12 H12A 120.0 . . ?
F2 C13 F1 112.0(12) . . ?
F2 C13 C14 93.4(14) . . ?
F1 C13 C14 95.4(13) . . ?
F2 C13 Cu1 117.8(11) . . ?
F1 C13 Cu1 119.4(10) . . ?
C14 C13 Cu1 113.2(12) . . ?
F4 C14 F5 117.8(15) . . ?
F4 C14 F3 107.3(15) . . ?
F5 C14 F3 113.1(15) . . ?
F4 C14 C13 110.0(14) . . ?
F5 C14 C13 105.9(15) . . ?
F3 C14 C13 101.5(14) . . ?
F5 C13' F2 141(3) . . ?
F5 C13' C14' 105(3) . . ?
F2 C13' C14' 115(4) . . ?
F5 C13' Cu1 103(2) . . ?
F2 C13' Cu1 95(2) . . ?
C14' C13' Cu1 69(2) . . ?
F1 C14' F3 137(3) . . ?
F1 C14' C13' 102(3) . . ?
F3 C14' C13' 113(4) . . ?
F1 C14' F4 89(2) . . ?
F3 C14' F4 85(2) . . ?
C13' C14' F4 63(2) . . ?
F1 C14' Cu1 98(2) . . ?
F3 C14' Cu1 114(2) . . ?
C13' C14' Cu1 74(2) . . ?
F4 C14' Cu1 137.3(18) . . ?

_refine_diff_density_max         0.724
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.099



