# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_mo_vipa_mami980_1_p21n
_database_code_depnum_ccdc_archive 'CCDC 2410335'
loop_
_audit_author_name
_audit_author_address
'Alexander Prado-Roler'
;University of Vienna
Austria
;
_audit_update_record             
;
2024-12-14 deposited with the CCDC.	2025-06-06 downloaded from the CCDC.
;
_audit_creation_date             2024-11-25
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.11.02 svn.r19aeb66f for OlexSys, GUI svn.r7078)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H5 Cl4 F'
_chemical_formula_sum            'C8 H5 Cl4 F'
_chemical_formula_weight         261.92
_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'
Cl Cl 0.1484 0.1585 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.8894(3)
_cell_length_b                   6.0908(3)
_cell_length_c                   16.5497(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.434(2)
_cell_angle_gamma                90
_cell_volume                     990.58(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6263
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.552
_cell_measurement_theta_min      2.533
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_T_max  0.5645
_exptl_absorpt_correction_T_min  0.5352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0512 before and 0.0366 after correction.
The Ratio of minimum to maximum transmission is 0.9481.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10830
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_min         2.292
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.962
_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_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2415
_reflns_number_total             2927
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0233
_refine_ls_restrained_S_all      1.120
_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)+(0.0256P)²+0.2204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0596
_refine_special_details          
;
_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All F(H) groups
2. Restrained distances
 F1B-C1
 1.38 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1B) = Uanis(F1A)
4. Others
 Sof(H1B)=Sof(F1B)=1-FVAR(1)
 Sof(F1A)=Sof(H1A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.35875(3) 0.25531(5) 0.42849(2) 0.02229(8) Uani 1 1 d . . . . .
Cl2 Cl 0.66849(3) 0.11043(5) 0.09073(2) 0.01644(8) Uani 1 1 d . . . . .
Cl3 Cl 0.68660(3) -0.32807(6) 0.02586(2) 0.02267(8) Uani 1 1 d . . . . .
Cl4 Cl 0.77557(3) -0.24426(5) 0.19502(2) 0.01768(8) Uani 1 1 d . . . . .
F1A F 0.49685(8) -0.44474(12) 0.14126(5) 0.0207(2) Uani 0.969(2) 1 d . . P A 1
C1 C 0.50728(12) -0.21934(19) 0.13222(8) 0.0154(2) Uani 1 1 d D . . . .
H1B H 0.516034 -0.374546 0.151816 0.018 Uiso 0.031(2) 1 calc R U P A 2
C2 C 0.46846(11) -0.10572(19) 0.20686(7) 0.0131(2) Uani 1 1 d . . . . .
C3 C 0.40546(11) 0.0999(2) 0.19902(8) 0.0135(2) Uani 1 1 d . . . . .
H3 H 0.386546 0.164453 0.146721 0.016 Uiso 1 1 calc R U . . .
C4 C 0.37028(11) 0.21048(19) 0.26697(8) 0.0143(2) Uani 1 1 d . . . . .
H4 H 0.328430 0.350931 0.261773 0.017 Uiso 1 1 calc R U . . .
C5 C 0.39747(11) 0.1118(2) 0.34270(8) 0.0144(2) Uani 1 1 d . . . . .
C6 C 0.45591(11) -0.0951(2) 0.35186(8) 0.0159(2) Uani 1 1 d . . . . .
H6 H 0.471073 -0.161725 0.403991 0.019 Uiso 1 1 calc R U . . .
C7 C 0.49185(12) -0.2031(2) 0.28349(8) 0.0147(2) Uani 1 1 d . . . . .
H7 H 0.532658 -0.344291 0.288927 0.018 Uiso 1 1 calc R U . . .
C8 C 0.65413(12) -0.17325(19) 0.11287(7) 0.0139(2) Uani 1 1 d . . . . .
F1B F 0.426(3) -0.242(4) 0.0689(13) 0.0207(2) Uani 0.031(2) 1 d D . P A 2
H1A H 0.448(2) -0.185(3) 0.0840(13) 0.025 Uiso 0.969(2) 1 d . U P A 1


_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
Cl1 C5 1.7458(12) . ?
Cl2 C8 1.7752(12) . ?
Cl3 C8 1.7802(12) . ?
Cl4 C8 1.7641(12) . ?
F1A C1 1.3861(14) . ?
C1 H1B 1.0000 . ?
C1 C2 1.5028(17) . ?
C1 C8 1.5474(16) . ?
C1 F1B 1.257(17) . ?
C1 H1A 0.96(2) . ?
C2 C3 1.3982(17) . ?
C2 C7 1.3956(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3883(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3888(18) . ?
C5 C6 1.3875(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3892(18) . ?
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
F1A C1 C2 109.78(10) . . ?
F1A C1 C8 106.56(10) . . ?
F1A C1 H1A 105.2(12) . . ?
C2 C1 H1B 100.9 . . ?
C2 C1 C8 114.75(10) . . ?
C2 C1 H1A 113.2(12) . . ?
C8 C1 H1B 100.9 . . ?
C8 C1 H1A 106.7(12) . . ?
F1B C1 H1B 100.9 . . ?
F1B C1 C2 122.5(13) . . ?
F1B C1 C8 112.2(13) . . ?
C3 C2 C1 119.24(11) . . ?
C7 C2 C1 121.31(11) . . ?
C7 C2 C3 119.45(11) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.59(11) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.70(11) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 Cl1 118.64(9) . . ?
C6 C5 Cl1 119.50(10) . . ?
C6 C5 C4 121.86(11) . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.85(11) . . ?
C7 C6 H6 120.6 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.50(11) . . ?
C6 C7 H7 119.8 . . ?
Cl2 C8 Cl3 108.83(7) . . ?
Cl4 C8 Cl2 109.53(6) . . ?
Cl4 C8 Cl3 108.94(6) . . ?
C1 C8 Cl2 108.54(8) . . ?
C1 C8 Cl3 109.26(8) . . ?
C1 C8 Cl4 111.69(9) . . ?

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
Cl1 C5 C6 C7 -177.10(9) . . . . ?
F1A C1 C2 C3 -147.69(10) . . . . ?
F1A C1 C2 C7 31.15(15) . . . . ?
F1A C1 C8 Cl2 174.32(8) . . . . ?
F1A C1 C8 Cl3 55.78(11) . . . . ?
F1A C1 C8 Cl4 -64.82(11) . . . . ?
C1 C2 C3 C4 -179.00(10) . . . . ?
C1 C2 C7 C6 179.67(10) . . . . ?
C2 C1 C8 Cl2 -63.96(12) . . . . ?
C2 C1 C8 Cl3 177.50(9) . . . . ?
C2 C1 C8 Cl4 56.90(12) . . . . ?
C2 C3 C4 C5 -0.73(16) . . . . ?
C3 C2 C7 C6 -1.49(17) . . . . ?
C3 C4 C5 Cl1 177.74(8) . . . . ?
C3 C4 C5 C6 -1.36(17) . . . . ?
C4 C5 C6 C7 2.00(17) . . . . ?
C5 C6 C7 C2 -0.54(17) . . . . ?
C7 C2 C3 C4 2.14(17) . . . . ?
C8 C1 C2 C3 92.36(13) . . . . ?
C8 C1 C2 C7 -88.80(13) . . . . ?
F1B C1 C2 C3 -49.5(14) . . . . ?
F1B C1 C2 C7 129.3(14) . . . . ?
F1B C1 C8 Cl2 81.8(13) . . . . ?
F1B C1 C8 Cl3 -36.7(13) . . . . ?
F1B C1 C8 Cl4 -157.3(13) . . . . ?

