# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_D8C_23064_0m_4_a
_database_code_depnum_ccdc_archive 'CCDC 2433662'
loop_
_audit_author_name
_audit_author_address
'Michel Grosse'
;Justus Liebig University Giessen
Germany
;
_audit_update_record             
;
2025-03-24 deposited with the CCDC.	2025-12-29 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            'C24 H16 F4'
_chemical_formula_weight         380.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   4.8992(13)
_cell_length_b                   8.306(2)
_cell_length_c                   20.760(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.874(13)
_cell_angle_gamma                90
_cell_volume                     844.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4553
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      29.39

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.649
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.031
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.284011
_exptl_absorpt_correction_T_max  0.745906
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker CMOS-PHOTONIII-C14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            2939
_diffrn_reflns_av_unetI/netI     0.1164
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.641
_diffrn_reflns_theta_max         29.571
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2939
_reflns_number_gt                2120
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'APEX4 v2021.10-0 (Bruker-AXS, 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1523P)²+2.3918P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2939
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1442
_refine_ls_R_factor_gt           0.1086
_refine_ls_wR_factor_ref         0.3015
_refine_ls_wR_factor_gt          0.2769
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
F1 F 0.2481(6) 0.5495(4) 0.72360(14) 0.0219(7) Uani 1 1 d . . . . .
F2 F 0.5039(7) 1.1100(4) 0.60321(15) 0.0260(8) Uani 1 1 d . . . . .
C1 C 0.8460(9) 0.5399(5) 0.5836(2) 0.0130(8) Uani 1 1 d . . . . .
C2 C 0.9092(9) 0.6861(6) 0.5510(2) 0.0146(9) Uani 1 1 d . . . . .
C3 C 1.1177(10) 0.6888(5) 0.4992(2) 0.0140(9) Uani 1 1 d . . . . .
H3A H 1.277303 0.628962 0.514371 0.017 Uiso 1 1 calc R U . . .
H3B H 1.173954 0.799309 0.492489 0.017 Uiso 1 1 calc R U . . .
C4 C 0.9838(9) 0.3831(5) 0.5669(2) 0.0140(9) Uani 1 1 d . . . . .
H4A H 0.951128 0.305247 0.600604 0.017 Uiso 1 1 calc R U . . .
H4B H 1.179252 0.400844 0.565807 0.017 Uiso 1 1 calc R U . . .
C5 C 0.6519(9) 0.5404(5) 0.6305(2) 0.0140(9) Uani 1 1 d . . . . .
H5 H 0.610737 0.444835 0.651476 0.017 Uiso 1 1 calc R U . . .
C6 C 0.5153(9) 0.6833(6) 0.6472(2) 0.0138(9) Uani 1 1 d . . . . .
C7 C 0.5795(10) 0.8296(5) 0.6153(2) 0.0143(9) Uani 1 1 d . . . . .
C8 C 0.7789(10) 0.8268(5) 0.5675(2) 0.0157(9) Uani 1 1 d . . . . .
H8 H 0.823204 0.922000 0.546772 0.019 Uiso 1 1 calc R U . . .
C9 C 0.3132(10) 0.6905(6) 0.6947(2) 0.0161(9) Uani 1 1 d . . . . .
C10 C 0.1835(10) 0.8281(6) 0.7109(2) 0.0196(10) Uani 1 1 d . . . . .
H10 H 0.052553 0.826838 0.742362 0.024 Uiso 1 1 calc R U . . .
C11 C 0.2491(10) 0.9736(6) 0.6797(2) 0.0187(10) Uani 1 1 d . . . . .
H11 H 0.163410 1.069421 0.690442 0.022 Uiso 1 1 calc R U . . .
C12 C 0.4401(10) 0.9706(6) 0.6336(2) 0.0175(9) 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
F1 C9 1.359(6) . ?
F2 C12 1.360(6) . ?
C1 C5 1.383(6) . ?
C1 C2 1.429(6) . ?
C1 C4 1.512(6) . ?
C2 C8 1.380(7) . ?
C2 C3 1.507(6) . ?
C3 C4 1.563(6) 3_766 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.412(6) . ?
C5 H5 0.9300 . ?
C6 C9 1.422(6) . ?
C6 C7 1.423(6) . ?
C7 C12 1.414(7) . ?
C7 C8 1.415(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.356(7) . ?
C10 C11 1.413(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(7) . ?
C11 H11 0.9300 . ?

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
C5 C1 C2 119.7(4) . . ?
C5 C1 C4 119.1(4) . . ?
C2 C1 C4 121.2(4) . . ?
C8 C2 C1 119.5(4) . . ?
C8 C2 C3 119.6(4) . . ?
C1 C2 C3 120.9(4) . . ?
C2 C3 C4 114.6(4) . 3_766 ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 3_766 . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 3_766 . ?
H3A C3 H3B 107.6 . . ?
C1 C4 C3 113.5(4) . 3_766 ?
C1 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 3_766 . ?
C1 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 3_766 . ?
H4A C4 H4B 107.7 . . ?
C1 C5 C6 121.1(4) . . ?
C1 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C9 123.5(4) . . ?
C5 C6 C7 119.4(4) . . ?
C9 C6 C7 117.1(4) . . ?
C12 C7 C8 123.6(4) . . ?
C12 C7 C6 117.8(4) . . ?
C8 C7 C6 118.6(4) . . ?
C2 C8 C7 121.6(4) . . ?
C2 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 F1 119.9(4) . . ?
C10 C9 C6 123.4(4) . . ?
F1 C9 C6 116.7(4) . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 118.6(5) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
F2 C12 C11 119.0(4) . . ?
F2 C12 C7 117.4(4) . . ?
C11 C12 C7 123.6(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
C5 C1 C2 C8 1.1(7) . . . . ?
C4 C1 C2 C8 179.9(4) . . . . ?
C5 C1 C2 C3 -179.4(4) . . . . ?
C4 C1 C2 C3 -0.6(6) . . . . ?
C8 C2 C3 C4 -104.6(5) . . . 3_766 ?
C1 C2 C3 C4 75.9(5) . . . 3_766 ?
C5 C1 C4 C3 105.9(5) . . . 3_766 ?
C2 C1 C4 C3 -72.9(5) . . . 3_766 ?
C2 C1 C5 C6 -0.4(7) . . . . ?
C4 C1 C5 C6 -179.1(4) . . . . ?
C1 C5 C6 C9 179.6(5) . . . . ?
C1 C5 C6 C7 -0.3(6) . . . . ?
C5 C6 C7 C12 -179.5(4) . . . . ?
C9 C6 C7 C12 0.5(6) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
C9 C6 C7 C8 -179.7(4) . . . . ?
C1 C2 C8 C7 -1.2(7) . . . . ?
C3 C2 C8 C7 179.3(4) . . . . ?
C12 C7 C8 C2 -179.7(4) . . . . ?
C6 C7 C8 C2 0.6(7) . . . . ?
C5 C6 C9 C10 179.5(4) . . . . ?
C7 C6 C9 C10 -0.5(7) . . . . ?
C5 C6 C9 F1 -1.6(7) . . . . ?
C7 C6 C9 F1 178.3(4) . . . . ?
F1 C9 C10 C11 -178.8(5) . . . . ?
C6 C9 C10 C11 0.0(7) . . . . ?
C9 C10 C11 C12 0.5(8) . . . . ?
C10 C11 C12 F2 179.8(4) . . . . ?
C10 C11 C12 C7 -0.5(8) . . . . ?
C8 C7 C12 F2 -0.1(7) . . . . ?
C6 C7 C12 F2 179.6(4) . . . . ?
C8 C7 C12 C11 -179.8(5) . . . . ?
C6 C7 C12 C11 0.0(7) . . . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.105



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
