# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_4-1
_database_code_depnum_ccdc_archive 'CCDC 2190192'
loop_
_audit_author_name
_audit_author_address
'Jiuzhong Huang'
;Gannan Medical University
China
;
_audit_update_record             
;
2022-07-14 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_audit_creation_date             2021-11-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 Cl F2 N O'
_chemical_formula_sum            'C12 H12 Cl F2 N O'
_chemical_formula_weight         259.68
_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                   8.8005(12)
_cell_length_b                   11.8789(16)
_cell_length_c                   12.2138(17)
_cell_angle_alpha                90.098(11)
_cell_angle_beta                 97.747(11)
_cell_angle_gamma                110.017(13)
_cell_volume                     1187.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2221
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.2000
_cell_measurement_theta_min      2.4260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4184
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.421
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00  40.00   1.00    2.50    --   12.05 -57.00  60.00   97
  2  ω    -12.00  76.00   1.00    2.50    --   12.05  73.00 -29.00   88
  3  ω    -11.00  85.00   1.00    2.50    --   12.05  57.00-150.00   96
  4  ω     -2.00  12.00   1.00    6.00    --   11.82 -99.00   0.00   14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0638037000
_diffrn_orient_matrix_UB_12      0.0565710000
_diffrn_orient_matrix_UB_13      0.0045456000
_diffrn_orient_matrix_UB_21      -0.0283384000
_diffrn_orient_matrix_UB_22      0.0163354000
_diffrn_orient_matrix_UB_23      0.0471601000
_diffrn_orient_matrix_UB_31      0.0513821000
_diffrn_orient_matrix_UB_32      -0.0241278000
_diffrn_orient_matrix_UB_33      0.0346309000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3124
_reflns_number_total             4184
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.144
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0787
_refine_ls_restrained_S_all      1.048
_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)+(0.1238P)²+1.3044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2200
_refine_ls_wR_factor_ref         0.2424
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.432(4)
 0.568(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C9(H9), C20(H20)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C14(H14), C16(H16), C17(H17),
 C19(H19), C24(H24)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_atom_sites_solution_hydrogens   geom
_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 0.17512(19) 0.60525(16) 1.25327(12) 0.0471(5) Uani 1 1 d . . . . .
F1 F 0.3845(5) 0.2122(3) 0.7364(3) 0.0520(10) Uani 1 1 d . . . . .
F2 F 0.1513(4) 0.2013(3) 0.6511(3) 0.0466(9) Uani 1 1 d . . . . .
O1 O 0.2408(4) 0.3033(3) 0.8111(3) 0.0337(9) Uani 1 1 d . . . . .
N1 N 0.2975(5) 0.4214(4) 0.5547(4) 0.0289(10) Uani 1 1 d . . . . .
C1 C 0.2861(6) 0.4696(5) 0.9391(4) 0.0243(11) Uani 1 1 d . . . . .
C2 C 0.2077(6) 0.3902(5) 1.0128(5) 0.0343(13) Uani 1 1 d . . . . .
H2 H 0.175530 0.308075 0.996669 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1765(7) 0.4310(6) 1.1102(5) 0.0380(14) Uani 1 1 d . . . . .
H3 H 0.125231 0.377003 1.160202 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2222(6) 0.5532(5) 1.1326(4) 0.0311(12) Uani 1 1 d . . . . .
C5 C 0.3033(6) 0.6350(5) 1.0617(4) 0.0321(13) Uani 1 1 d . . . . .
H5 H 0.335338 0.716967 1.078447 0.039 Uiso 1 1 calc R U . . .
C6 C 0.3360(6) 0.5930(5) 0.9654(4) 0.0274(12) Uani 1 1 d . . . . .
H6 H 0.391841 0.647290 0.917308 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3134(6) 0.4277(4) 0.8333(4) 0.0247(11) Uani 1 1 d . . . . .
C8 C 0.3905(6) 0.4831(5) 0.7532(4) 0.0274(12) Uani 1 1 d . . . . .
H8 H 0.447171 0.565128 0.754024 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3740(6) 0.3948(5) 0.6596(4) 0.0287(12) Uani 1 1 d . . . . .
H9 H 0.483509 0.395979 0.650526 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2846(6) 0.2763(5) 0.7118(5) 0.0315(12) Uani 1 1 d . . . . .
C12 C 0.1352(6) 0.4262(6) 0.5540(5) 0.0363(13) Uani 1 1 d . . . . .
H12A H 0.059718 0.346998 0.561122 0.054 Uiso 1 1 calc R U . . .
H12B H 0.102338 0.456967 0.485698 0.054 Uiso 1 1 calc R U . . .
H12C H 0.135778 0.477781 0.614793 0.054 Uiso 1 1 calc R U . . .
C13 C 0.3084(8) 0.3501(7) 0.4594(5) 0.0440(16) Uani 1 1 d . . . . .
H13A H 0.265455 0.377489 0.392308 0.066 Uiso 1 1 calc R U . . .
H13B H 0.246353 0.267071 0.466218 0.066 Uiso 1 1 calc R U . . .
H13C H 0.420685 0.359124 0.457394 0.066 Uiso 1 1 calc R U . . .
Cl2 Cl 0.17532(18) 0.73702(15) 0.75766(11) 0.0441(4) Uani 1 1 d . . . . .
F3 F 0.1514(4) 1.1193(3) 0.1502(3) 0.0410(8) Uani 1 1 d . . . . .
F4 F 0.3840(4) 1.2280(3) 0.2383(3) 0.0459(9) Uani 1 1 d . . . . .
O2 O 0.2342(4) 1.0637(3) 0.3108(3) 0.0337(9) Uani 1 1 d . . . . .
N2 N 0.2965(5) 0.9690(4) 0.0589(4) 0.0293(10) Uani 1 1 d . . . . .
C11 C 0.2809(5) 0.9225(4) 0.4422(4) 0.0207(10) Uani 1 1 d . . . . .
C14 C 0.3044(6) 0.7727(5) 0.5674(4) 0.0273(11) Uani 1 1 d . . . . .
H14 H 0.341711 0.709870 0.586199 0.033 Uiso 1 1 calc R U . . .
C15 C 0.2184(6) 0.8101(5) 0.6364(4) 0.0278(12) Uani 1 1 d . . . . .
C16 C 0.1641(6) 0.9056(5) 0.6124(4) 0.0333(13) Uani 1 1 d . . . . .
H16 H 0.108018 0.931514 0.660510 0.040 Uiso 1 1 calc R U . . .
C17 C 0.1969(6) 0.9611(5) 0.5137(4) 0.0294(12) Uani 1 1 d . . . . .
H17 H 0.161904 1.025031 0.495319 0.035 Uiso 1 1 calc R U . . .
C18 C 0.3092(5) 0.9775(5) 0.3361(4) 0.0235(11) Uani 1 1 d . . . . .
C19 C 0.3887(6) 0.9624(5) 0.2561(4) 0.0273(11) Uani 1 1 d . . . . .
H19 H 0.447935 0.910683 0.258510 0.033 Uiso 1 1 calc R U . . .
C20 C 0.3718(6) 1.0374(5) 0.1629(4) 0.0260(11) Uani 1 1 d . . . . .
H20 H 0.481234 1.091372 0.153381 0.031 Uiso 1 1 calc R U . . .
C21 C 0.2832(6) 1.1119(5) 0.2138(4) 0.0272(11) Uani 1 1 d . . . . .
C22 C 0.3064(7) 1.0423(6) -0.0374(5) 0.0382(14) Uani 1 1 d . . . . .
H22A H 0.237662 1.089701 -0.034625 0.057 Uiso 1 1 calc R U . . .
H22B H 0.270612 0.991212 -0.103613 0.057 Uiso 1 1 calc R U . . .
H22C H 0.417327 1.094354 -0.037191 0.057 Uiso 1 1 calc R U . . .
C23 C 0.1353(6) 0.8810(5) 0.0586(5) 0.0338(13) Uani 1 1 d . . . . .
H23A H 0.131999 0.839455 0.126099 0.051 Uiso 1 1 calc R U . . .
H23B H 0.110696 0.824492 -0.003213 0.051 Uiso 1 1 calc R U . . .
H23C H 0.056088 0.920459 0.052692 0.051 Uiso 1 1 calc R U . . .
C24 C 0.3351(6) 0.8290(5) 0.4701(4) 0.0247(11) Uani 1 1 d . . . . .
H24 H 0.392791 0.803641 0.422855 0.030 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
Cl1 C4 1.750(5) . ?
F1 C10 1.352(6) . ?
F2 C10 1.330(6) . ?
O1 C7 1.404(6) . ?
O1 C10 1.390(6) . ?
N1 C9 1.453(7) . ?
N1 C12 1.448(7) . ?
N1 C13 1.472(7) . ?
C1 C2 1.378(7) . ?
C1 C6 1.402(7) . ?
C1 C7 1.463(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(8) . ?
C4 C5 1.378(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.314(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.508(7) . ?
C9 H9 0.9800 . ?
C9 C10 1.545(8) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
Cl2 C15 1.738(5) . ?
F3 C21 1.336(6) . ?
F4 C21 1.367(6) . ?
O2 C18 1.410(6) . ?
O2 C21 1.374(6) . ?
N2 C20 1.453(6) . ?
N2 C22 1.459(7) . ?
N2 C23 1.446(7) . ?
C11 C17 1.387(7) . ?
C11 C18 1.465(7) . ?
C11 C24 1.377(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(7) . ?
C14 C24 1.378(7) . ?
C15 C16 1.392(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.392(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.321(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.470(7) . ?
C20 H20 0.9800 . ?
C20 C21 1.543(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24 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
C10 O1 C7 107.5(4) . . ?
C9 N1 C13 113.8(5) . . ?
C12 N1 C9 115.7(4) . . ?
C12 N1 C13 112.5(4) . . ?
C2 C1 C6 118.9(5) . . ?
C2 C1 C7 121.4(5) . . ?
C6 C1 C7 119.7(5) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.8(5) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 Cl1 119.3(4) . . ?
C5 C4 Cl1 119.2(4) . . ?
C5 C4 C3 121.5(5) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.7(5) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.9(5) . . ?
C5 C6 H6 119.6 . . ?
O1 C7 C1 114.1(4) . . ?
C8 C7 O1 112.8(5) . . ?
C8 C7 C1 133.1(5) . . ?
C7 C8 H8 124.8 . . ?
C7 C8 C9 110.4(5) . . ?
C9 C8 H8 124.8 . . ?
N1 C9 C8 113.5(4) . . ?
N1 C9 H9 108.3 . . ?
N1 C9 C10 118.0(4) . . ?
C8 C9 H9 108.3 . . ?
C8 C9 C10 99.8(4) . . ?
C10 C9 H9 108.3 . . ?
F1 C10 O1 106.8(4) . . ?
F1 C10 C9 110.9(4) . . ?
F2 C10 F1 105.5(4) . . ?
F2 C10 O1 107.8(4) . . ?
F2 C10 C9 116.6(5) . . ?
O1 C10 C9 108.7(4) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C21 O2 C18 106.8(4) . . ?
C20 N2 C22 114.0(5) . . ?
C23 N2 C20 115.9(4) . . ?
C23 N2 C22 112.3(4) . . ?
C17 C11 C18 121.0(5) . . ?
C24 C11 C17 119.5(5) . . ?
C24 C11 C18 119.5(5) . . ?
C15 C14 H14 120.3 . . ?
C15 C14 C24 119.4(5) . . ?
C24 C14 H14 120.3 . . ?
C14 C15 Cl2 119.6(4) . . ?
C14 C15 C16 121.9(5) . . ?
C16 C15 Cl2 118.6(4) . . ?
C15 C16 H16 121.2 . . ?
C17 C16 C15 117.5(5) . . ?
C17 C16 H16 121.2 . . ?
C11 C17 C16 121.1(5) . . ?
C11 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
O2 C18 C11 114.7(4) . . ?
C19 C18 O2 111.6(5) . . ?
C19 C18 C11 133.7(5) . . ?
C18 C19 H19 124.2 . . ?
C18 C19 C20 111.6(5) . . ?
C20 C19 H19 124.2 . . ?
N2 C20 C19 113.6(4) . . ?
N2 C20 H20 108.1 . . ?
N2 C20 C21 118.9(4) . . ?
C19 C20 H20 108.1 . . ?
C19 C20 C21 99.5(4) . . ?
C21 C20 H20 108.1 . . ?
F3 C21 F4 105.2(4) . . ?
F3 C21 O2 107.3(4) . . ?
F3 C21 C20 115.6(4) . . ?
F4 C21 O2 107.6(4) . . ?
F4 C21 C20 111.4(4) . . ?
O2 C21 C20 109.3(4) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 C24 C14 120.6(5) . . ?
C11 C24 H24 119.7 . . ?
C14 C24 H24 119.7 . . ?

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 C4 C5 C6 -178.3(4) . . . . ?
O1 C7 C8 C9 1.2(6) . . . . ?
N1 C9 C10 F1 127.3(5) . . . . ?
N1 C9 C10 F2 6.6(7) . . . . ?
N1 C9 C10 O1 -115.5(5) . . . . ?
C1 C2 C3 C4 1.1(9) . . . . ?
C1 C7 C8 C9 -177.7(5) . . . . ?
C2 C1 C6 C5 -1.9(8) . . . . ?
C2 C1 C7 O1 5.4(7) . . . . ?
C2 C1 C7 C8 -175.8(6) . . . . ?
C2 C3 C4 Cl1 177.3(4) . . . . ?
C2 C3 C4 C5 -2.3(9) . . . . ?
C3 C4 C5 C6 1.3(8) . . . . ?
C4 C5 C6 C1 0.8(8) . . . . ?
C6 C1 C2 C3 0.9(8) . . . . ?
C6 C1 C7 O1 -172.7(4) . . . . ?
C6 C1 C7 C8 6.1(9) . . . . ?
C7 O1 C10 F1 112.1(4) . . . . ?
C7 O1 C10 F2 -135.0(4) . . . . ?
C7 O1 C10 C9 -7.7(5) . . . . ?
C7 C1 C2 C3 -177.2(5) . . . . ?
C7 C1 C6 C5 176.2(5) . . . . ?
C7 C8 C9 N1 121.1(5) . . . . ?
C7 C8 C9 C10 -5.4(5) . . . . ?
C8 C9 C10 F1 -109.3(5) . . . . ?
C8 C9 C10 F2 130.0(5) . . . . ?
C8 C9 C10 O1 7.8(5) . . . . ?
C10 O1 C7 C1 -176.7(4) . . . . ?
C10 O1 C7 C8 4.3(6) . . . . ?
C12 N1 C9 C8 -58.2(6) . . . . ?
C12 N1 C9 C10 58.0(6) . . . . ?
C13 N1 C9 C8 169.2(5) . . . . ?
C13 N1 C9 C10 -74.6(6) . . . . ?
Cl2 C15 C16 C17 -178.6(4) . . . . ?
O2 C18 C19 C20 -1.6(6) . . . . ?
N2 C20 C21 F3 -7.9(7) . . . . ?
N2 C20 C21 F4 -127.9(5) . . . . ?
N2 C20 C21 O2 113.2(5) . . . . ?
C11 C18 C19 C20 176.9(5) . . . . ?
C14 C15 C16 C17 1.5(7) . . . . ?
C15 C14 C24 C11 0.4(7) . . . . ?
C15 C16 C17 C11 -0.2(7) . . . . ?
C17 C11 C18 O2 -4.7(6) . . . . ?
C17 C11 C18 C19 176.9(5) . . . . ?
C17 C11 C24 C14 0.9(7) . . . . ?
C18 O2 C21 F3 136.3(4) . . . . ?
C18 O2 C21 F4 -111.0(4) . . . . ?
C18 O2 C21 C20 10.2(5) . . . . ?
C18 C11 C17 C16 177.3(5) . . . . ?
C18 C11 C24 C14 -177.5(4) . . . . ?
C18 C19 C20 N2 -120.3(5) . . . . ?
C18 C19 C20 C21 7.1(5) . . . . ?
C19 C20 C21 F3 -131.7(4) . . . . ?
C19 C20 C21 F4 108.3(4) . . . . ?
C19 C20 C21 O2 -10.5(5) . . . . ?
C21 O2 C18 C11 175.5(4) . . . . ?
C21 O2 C18 C19 -5.7(5) . . . . ?
C22 N2 C20 C19 -169.3(4) . . . . ?
C22 N2 C20 C21 74.2(6) . . . . ?
C23 N2 C20 C19 58.0(6) . . . . ?
C23 N2 C20 C21 -58.5(6) . . . . ?
C24 C11 C17 C16 -1.0(7) . . . . ?
C24 C11 C18 O2 173.7(4) . . . . ?
C24 C11 C18 C19 -4.8(8) . . . . ?
C24 C14 C15 Cl2 178.5(4) . . . . ?
C24 C14 C15 C16 -1.6(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.403
_oxdiff_exptl_absorpt_empirical_full_min 0.629
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.432(4)
2 0.568(4)

