# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_testt1
_database_code_depnum_ccdc_archive 'CCDC 2264158'
loop_
_audit_author_name
_audit_author_address
'Hazel Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2023-05-19 deposited with the CCDC.	2023-06-26 downloaded from the CCDC.
;
_audit_creation_date             2023-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 F4 N2 O2, 2(C H Cl3)'
_chemical_formula_sum            'C22 H22 Cl6 F4 N2 O2'
_chemical_formula_weight         635.11
_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'
N N 0.0061 0.0033 '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'

_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                   5.7583(2)
_cell_length_b                   10.0636(4)
_cell_length_c                   12.6561(5)
_cell_angle_alpha                66.9880(10)
_cell_angle_beta                 86.9530(10)
_cell_angle_gamma                87.6390(10)
_cell_volume                     673.93(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.916
_cell_measurement_theta_min      3.302
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0986 before and 0.0422 after correction.
The Ratio of minimum to maximum transmission is 0.8443.
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    1.565
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.268
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38662
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.952
_diffrn_reflns_theta_min         1.750
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON III C7'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CPAD
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Venture dual source kappa CPAD'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω-scan'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\uS microsource'
_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                3004
_reflns_number_total             3236
_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 v8.39.0 (Bruker, 2018)'
_computing_data_collection       'Bruker SC-XRD Suite'
_computing_data_reduction        'SAINT v8.39.0 (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.032
_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)+(0.0252P)²+0.4852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0693
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
_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
O1 O 0.39679(16) 0.33718(10) 0.62253(8) 0.01884(19) Uani 1 1 d . . . . .
C1 C -0.0819(2) 0.22554(13) 0.50147(11) 0.0159(2) Uani 1 1 d . . . . .
H1A H -0.238363 0.259852 0.517278 0.019 Uiso 1 1 calc R U . . .
H1B H -0.063640 0.122879 0.553729 0.019 Uiso 1 1 calc R U . . .
N1 N 0.09570(18) 0.31049(11) 0.52501(9) 0.0135(2) Uani 1 1 d . . . . .
F1 F 0.43237(17) 0.06610(9) 0.75181(8) 0.0315(2) Uani 1 1 d . . . . .
F2 F 0.39713(16) 0.04311(9) 0.58926(7) 0.02805(19) Uani 1 1 d . . . . .
C2 C -0.0635(2) 0.23761(13) 0.37829(11) 0.0157(2) Uani 1 1 d . . . . .
C3 C 0.1327(2) 0.18328(13) 0.33791(11) 0.0178(2) Uani 1 1 d . . . . .
H3 H 0.255643 0.138672 0.387926 0.021 Uiso 1 1 calc R U . . .
C4 C 0.1496(2) 0.19400(15) 0.22494(12) 0.0217(3) Uani 1 1 d . . . . .
H4 H 0.284050 0.156888 0.197999 0.026 Uiso 1 1 calc R U . . .
C5 C -0.0296(3) 0.25887(16) 0.15126(12) 0.0248(3) Uani 1 1 d . . . . .
H5 H -0.018220 0.265736 0.074144 0.030 Uiso 1 1 calc R U . . .
C6 C -0.2250(3) 0.31352(16) 0.19072(13) 0.0256(3) Uani 1 1 d . . . . .
H6 H -0.347626 0.358088 0.140509 0.031 Uiso 1 1 calc R U . . .
C7 C -0.2418(2) 0.30319(15) 0.30378(12) 0.0210(3) Uani 1 1 d . . . . .
H7 H -0.375796 0.341156 0.330289 0.025 Uiso 1 1 calc R U . . .
C8 C 0.2616(2) 0.25971(13) 0.60231(10) 0.0145(2) Uani 1 1 d . . . . .
C9 C 0.2886(2) 0.09451(14) 0.66458(11) 0.0183(2) Uani 1 1 d . . . . .
H9 H 0.134386 0.048732 0.692873 0.022 Uiso 1 1 calc R U . . .
C10 C 0.0743(2) 0.46756(12) 0.46386(10) 0.0137(2) Uani 1 1 d . . . . .
H10A H 0.001685 0.490482 0.389403 0.016 Uiso 1 1 calc R U . . .
H10B H 0.230684 0.510124 0.448143 0.016 Uiso 1 1 calc R U . . .
Cl1 Cl 0.76193(7) 0.43970(4) 0.84217(3) 0.03179(10) Uani 1 1 d . . . . .
Cl2 Cl 0.46202(8) 0.20198(5) 0.96702(4) 0.04269(12) Uani 1 1 d . . . . .
Cl3 Cl 0.89520(7) 0.15037(5) 0.86480(4) 0.03866(11) Uani 1 1 d . . . . .
C11 C 0.6608(2) 0.27319(15) 0.85018(11) 0.0202(3) Uani 1 1 d . . . . .
H11 H 0.581015 0.288884 0.777850 0.024 Uiso 1 1 calc R U . . .


_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
O1 C8 1.2274(15) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 N1 1.4728(15) . ?
C1 C2 1.5139(17) . ?
N1 C8 1.3412(16) . ?
N1 C10 1.4664(15) . ?
F1 C9 1.3479(15) . ?
F2 C9 1.3647(15) . ?
C2 C3 1.3941(18) . ?
C2 C7 1.3923(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3895(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.5417(17) . ?
C9 H9 1.0000 . ?
C10 C10 1.527(2) 2_566 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
Cl1 C11 1.7602(14) . ?
Cl2 C11 1.7522(14) . ?
Cl3 C11 1.7588(14) . ?
C11 H11 1.0000 . ?

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
H1A C1 H1B 107.9 . . ?
N1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
N1 C1 C2 111.95(10) . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C8 N1 C1 126.66(10) . . ?
C8 N1 C10 117.37(10) . . ?
C10 N1 C1 115.76(10) . . ?
C3 C2 C1 120.32(11) . . ?
C7 C2 C1 120.58(11) . . ?
C7 C2 C3 119.10(12) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.39(12) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.17(13) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.76(13) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.11(13) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.46(13) . . ?
C6 C7 H7 119.8 . . ?
O1 C8 N1 123.58(11) . . ?
O1 C8 C9 118.85(11) . . ?
N1 C8 C9 117.52(11) . . ?
F1 C9 F2 106.88(10) . . ?
F1 C9 C8 108.35(10) . . ?
F1 C9 H9 111.3 . . ?
F2 C9 C8 107.66(10) . . ?
F2 C9 H9 111.3 . . ?
C8 C9 H9 111.3 . . ?
N1 C10 C10 110.04(12) . 2_566 ?
N1 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C10 C10 H10A 109.7 2_566 . ?
C10 C10 H10B 109.7 2_566 . ?
H10A C10 H10B 108.2 . . ?
Cl1 C11 H11 108.9 . . ?
Cl2 C11 Cl1 110.19(7) . . ?
Cl2 C11 Cl3 109.70(8) . . ?
Cl2 C11 H11 108.9 . . ?
Cl3 C11 Cl1 110.26(7) . . ?
Cl3 C11 H11 108.9 . . ?

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
O1 C8 C9 F1 13.48(16) . . . . ?
O1 C8 C9 F2 -101.78(13) . . . . ?
C1 N1 C8 O1 -175.73(11) . . . . ?
C1 N1 C8 C9 7.03(18) . . . . ?
C1 N1 C10 C10 91.08(14) . . . 2_566 ?
C1 C2 C3 C4 179.86(11) . . . . ?
C1 C2 C7 C6 -179.68(12) . . . . ?
N1 C1 C2 C3 64.94(14) . . . . ?
N1 C1 C2 C7 -114.94(13) . . . . ?
N1 C8 C9 F1 -169.15(11) . . . . ?
N1 C8 C9 F2 75.60(14) . . . . ?
C2 C1 N1 C8 -119.60(13) . . . . ?
C2 C1 N1 C10 65.87(13) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C2 C7 C6 0.43(19) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
C7 C2 C3 C4 -0.25(19) . . . . ?
C8 N1 C10 C10 -83.98(15) . . . 2_566 ?
C10 N1 C8 O1 -1.28(17) . . . . ?
C10 N1 C8 C9 -178.52(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
