# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_3m
_database_code_depnum_ccdc_archive 'CCDC 2061451'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2021-02-06 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;
_audit_creation_date             2021-02-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C21 H17 F N2 O2), C H Cl3'
_chemical_formula_sum            'C43 H35 Cl3 F2 N4 O4'
_chemical_formula_weight         816.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 F1 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   27.3194(10)
_cell_length_b                   9.9217(2)
_cell_length_c                   18.9017(7)
_cell_angle_alpha                90
_cell_angle_beta                 131.359(6)
_cell_angle_gamma                90
_cell_volume                     3845.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5536
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2850
_cell_measurement_theta_min      4.3120
_shelx_estimated_absorpt_T_max   0.777
_shelx_estimated_absorpt_T_min   0.619
_exptl_absorpt_coefficient_mu    2.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9180
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.417
_diffrn_reflns_theta_min         4.312
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -18.00   1.00    4.84    --  -35.62 -49.00 177.00   86
  2  ω    -53.00  32.00   1.00    4.84    --  -35.62  49.00 -34.00   85
  3  ω    -14.00  11.00   1.00    4.84    --   35.62 -49.00 177.00   25
  4  ω     48.00 101.00   1.00    4.84    --   35.62  49.00 -34.00   53
  5  ω     42.00 124.00   1.00   19.35    --  107.12 -49.00 177.00   82
  6  ω     90.00 163.00   1.00   19.35    --  107.12  49.00 -34.00   73
  7  ω   -105.00 -35.00   1.00    4.84    --  -35.62-178.00  60.00   70
  8  ω   -108.00 -56.00   1.00    4.84    --  -35.62-178.00 150.00   52
  9  ω     23.00 101.00   1.00    4.84    --   35.62  38.00 120.00   78
 10  ω     57.00  82.00   1.00    4.84    --   35.62 178.00-150.00   25
 11  ω    106.00 151.00   1.00   19.35    --  107.12  61.00  90.00   45
 12  ω     38.00  87.00   1.00   19.35    --  107.12 -95.00   0.00   49
 13  ω     91.00 175.00   1.00   19.35    --  107.12  45.00 -90.00   84
 14  ω     87.00 125.00   1.00   19.35    --  107.12 -45.00  30.00   38
 15  ω    127.00 176.00   1.00   19.35    --  107.12  45.00-150.00   49
 16  ω     40.00 133.00   1.00   19.35    --  107.12 -77.00  90.00   93
 17  ω    100.00 126.00   1.00   19.35    --  107.12  45.00-150.00   26
 18  ω     39.00  72.00   1.00   19.35    --  107.12 -45.00  30.00   33
 19  ω     87.00 113.00   1.00   19.35    --  107.12-111.00-150.00   26
 20  ω     38.00  64.00   1.00   19.35    --  107.12-111.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0733794000
_diffrn_orient_matrix_UB_12      -0.0295097000
_diffrn_orient_matrix_UB_13      -0.0781622000
_diffrn_orient_matrix_UB_21      0.0144252000
_diffrn_orient_matrix_UB_22      -0.0889129000
_diffrn_orient_matrix_UB_23      -0.0512012000
_diffrn_orient_matrix_UB_31      0.0070947000
_diffrn_orient_matrix_UB_32      -0.1238789000
_diffrn_orient_matrix_UB_33      0.0552874000
_diffrn_oxdiff_digest_frames     
;
01695228e0516c1721678eb34954d9546500029be59
;
_diffrn_oxdiff_digest_hkl        
;
01958da5eb48271ec35b38f2b5111998b2cb18
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3268
_reflns_number_total             3671
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²+2.4218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1343
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2A-C22
 1.73 with sigma of 0.02
 H22_$1-C22_$1
 0.95 with sigma of 0.02
 H22-Cl1
 1.91 with sigma of 0.02
3. Rigid bond restraints
 Cl2, Cl2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(Cl2A) \\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(Cl2A) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl1) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(Cl2A)=1-FVAR(1)
 Sof(Cl2)=FVAR(1)
 Fixed Sof: Cl1(0.5) H22(0.5) C22(0.5)
6.a Ternary CH refined with riding coordinates:
 C17(H17)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15)
6.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C 0.40893(7) 0.34458(16) 0.39126(11) 0.0359(3) Uani 1 1 d . . . . .
F1 F 0.45702(6) 0.23540(12) 0.53652(7) 0.0620(3) Uani 1 1 d . . . . .
N1 N 0.44347(6) 0.11335(13) 0.40410(10) 0.0421(3) Uani 1 1 d . . . . .
H1 H 0.4853 0.1065 0.4448 0.051 Uiso 1 1 calc R . . . .
O1 O 0.42168(6) -0.09013(13) 0.43404(10) 0.0577(4) Uani 1 1 d . . . . .
C2 C 0.43380(8) 0.34922(18) 0.48331(12) 0.0453(4) Uani 1 1 d . . . . .
N2 N 0.41071(6) 0.22991(13) 0.34682(9) 0.0356(3) Uani 1 1 d . . . . .
O2 O 0.29636(5) 0.26622(11) 0.21863(7) 0.0360(3) Uani 1 1 d . . . . .
C3 C 0.43549(10) 0.4646(2) 0.52479(13) 0.0564(5) Uani 1 1 d . . . . .
H3 H 0.4532 0.4633 0.5870 0.068 Uiso 1 1 calc R . . . .
C4 C 0.41064(11) 0.5829(2) 0.47355(14) 0.0569(5) Uani 1 1 d . . . . .
H4 H 0.4116 0.6619 0.5009 0.068 Uiso 1 1 calc R . . . .
C5 C 0.38437(9) 0.58241(17) 0.38123(13) 0.0464(4) Uani 1 1 d . . . . .
H5 H 0.3667 0.6615 0.3462 0.056 Uiso 1 1 calc R . . . .
C6 C 0.38368(7) 0.46636(15) 0.33928(11) 0.0366(3) Uani 1 1 d . . . . .
C7 C 0.35135(7) 0.46832(15) 0.23805(11) 0.0364(3) Uani 1 1 d . . . . .
C8 C 0.36013(8) 0.57533(17) 0.19602(12) 0.0419(4) Uani 1 1 d . . . . .
C9 C 0.40766(9) 0.67756(19) 0.24915(15) 0.0531(5) Uani 1 1 d . . . . .
H9 H 0.4352 0.6766 0.3145 0.064 Uiso 1 1 calc R . . . .
C10 C 0.41373(11) 0.7779(2) 0.20563(18) 0.0659(6) Uani 1 1 d . . . . .
H10 H 0.4455 0.8439 0.2419 0.079 Uiso 1 1 calc R . . . .
C11 C 0.37288(13) 0.7824(2) 0.10750(19) 0.0731(7) Uani 1 1 d . . . . .
H11 H 0.3768 0.8523 0.0788 0.088 Uiso 1 1 calc R . . . .
C12 C 0.32754(13) 0.6851(2) 0.05426(17) 0.0672(6) Uani 1 1 d . . . . .
H12 H 0.3009 0.6883 -0.0110 0.081 Uiso 1 1 calc R . . . .
C13 C 0.31985(10) 0.57832(19) 0.09614(14) 0.0506(4) Uani 1 1 d . . . . .
C14 C 0.27323(11) 0.4759(2) 0.04104(13) 0.0569(5) Uani 1 1 d . . . . .
H14 H 0.2464 0.4790 -0.0242 0.068 Uiso 1 1 calc R . . . .
C15 C 0.26687(9) 0.37239(18) 0.08181(12) 0.0479(4) Uani 1 1 d . . . . .
H15 H 0.2364 0.3045 0.0449 0.057 Uiso 1 1 calc R . . . .
C16 C 0.30685(7) 0.36961(15) 0.18008(11) 0.0362(3) Uani 1 1 d . . . . .
C17 C 0.34595(7) 0.17005(15) 0.26583(11) 0.0346(3) Uani 1 1 d . . . . .
H17 H 0.3490 0.1306 0.2214 0.042 Uiso 1 1 calc R . . . .
C18 C 0.33372(7) 0.05748(15) 0.30751(11) 0.0380(3) Uani 1 1 d . . . . .
C19 C 0.40405(8) 0.01566(16) 0.38954(12) 0.0408(4) Uani 1 1 d . . . . .
C20 C 0.30320(8) 0.10875(18) 0.34748(13) 0.0464(4) Uani 1 1 d . . . . .
H20A H 0.3264 0.1870 0.3857 0.070 Uiso 1 1 calc GR . . . .
H20B H 0.3057 0.0395 0.3852 0.070 Uiso 1 1 calc GR . . . .
H20C H 0.2583 0.1318 0.2965 0.070 Uiso 1 1 calc GR . . . .
C21 C 0.29397(9) -0.05817(18) 0.23865(14) 0.0520(4) Uani 1 1 d . . . . .
H21A H 0.2510 -0.0266 0.1859 0.078 Uiso 1 1 calc GR . . . .
H21B H 0.2908 -0.1295 0.2698 0.078 Uiso 1 1 calc GR . . . .
H21C H 0.3150 -0.0913 0.2168 0.078 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.47898(10) 0.62523(15) 0.73999(16) 0.1028(6) Uani 0.5 1 d D U P A .
Cl2 Cl 0.5485(5) 0.8768(5) 0.8445(2) 0.138(2) Uani 0.694(18) 1 d . U P A 1
Cl2A Cl 0.5756(4) 0.8319(17) 0.8496(4) 0.118(3) Uani 0.306(18) 1 d D U P A 2
H22 H 0.469(3) 0.773(3) 0.792(4) 0.10(2) Uiso 0.5 1 d D . P . .
C22 C 0.4892(3) 0.7718(6) 0.7649(4) 0.0755(13) Uani 0.5 1 d D . P . .


_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
C1 C2 1.389(2) . ?
C1 N2 1.434(2) . ?
C1 C6 1.416(2) . ?
F1 C2 1.359(2) . ?
N1 H1 0.8600 . ?
N1 N2 1.4248(17) . ?
N1 C19 1.335(2) . ?
O1 C19 1.227(2) . ?
C2 C3 1.371(3) . ?
N2 C17 1.4990(19) . ?
O2 C16 1.3931(19) . ?
O2 C17 1.3945(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(2) . ?
C6 C7 1.486(2) . ?
C7 C8 1.438(2) . ?
C7 C16 1.370(2) . ?
C8 C9 1.414(3) . ?
C8 C13 1.425(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.397(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.354(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.419(3) . ?
C13 C14 1.410(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.362(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.401(2) . ?
C17 H17 0.9800 . ?
C17 C18 1.526(2) . ?
C18 C19 1.527(2) . ?
C18 C20 1.535(2) . ?
C18 C21 1.524(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
Cl1 Cl1 0.942(4) 2_656 ?
Cl1 Cl2A 2.441(14) 2_656 ?
Cl1 C22 1.497(6) . ?
Cl1 C22 1.729(5) 2_656 ?
Cl2 C22 1.901(6) 2_656 ?
Cl2 C22 1.659(7) . ?
Cl2A Cl1 2.441(13) 2_656 ?
Cl2A C22 1.870(7) . ?
Cl2A C22 1.763(9) 2_656 ?
C22 Cl1 1.729(5) 2_656 ?
C22 Cl2 1.901(6) 2_656 ?
C22 Cl2A 1.763(9) 2_656 ?
C22 H22 0.955(19) . ?
C22 C22 1.054(9) 2_656 ?

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
C2 C1 N2 125.61(14) . . ?
C2 C1 C6 116.85(15) . . ?
C6 C1 N2 117.39(14) . . ?
N2 N1 H1 122.7 . . ?
C19 N1 H1 122.7 . . ?
C19 N1 N2 114.60(12) . . ?
F1 C2 C1 120.16(16) . . ?
F1 C2 C3 116.61(16) . . ?
C3 C2 C1 123.22(16) . . ?
C1 N2 C17 116.01(11) . . ?
N1 N2 C1 116.50(13) . . ?
N1 N2 C17 100.33(11) . . ?
C16 O2 C17 112.95(11) . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.55(17) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.22(17) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.55(17) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 120.47(14) . . ?
C5 C6 C1 119.59(15) . . ?
C5 C6 C7 119.72(14) . . ?
C8 C7 C6 123.15(14) . . ?
C16 C7 C6 118.60(14) . . ?
C16 C7 C8 118.02(15) . . ?
C9 C8 C7 123.18(16) . . ?
C9 C8 C13 117.96(16) . . ?
C13 C8 C7 118.85(16) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.99(19) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 119.0(2) . . ?
C14 C13 C8 119.58(16) . . ?
C14 C13 C12 121.39(19) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.08(17) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.07(17) . . ?
C16 C15 H15 120.5 . . ?
O2 C16 C15 117.28(14) . . ?
C7 C16 O2 119.24(14) . . ?
C7 C16 C15 123.27(15) . . ?
N2 C17 H17 108.8 . . ?
N2 C17 C18 106.04(12) . . ?
O2 C17 N2 111.98(12) . . ?
O2 C17 H17 108.8 . . ?
O2 C17 C18 112.31(12) . . ?
C18 C17 H17 108.8 . . ?
C17 C18 C19 99.51(12) . . ?
C17 C18 C20 112.77(13) . . ?
C19 C18 C20 108.57(14) . . ?
C21 C18 C17 112.69(14) . . ?
C21 C18 C19 111.79(14) . . ?
C21 C18 C20 110.96(14) . . ?
N1 C19 C18 108.33(13) . . ?
O1 C19 N1 125.56(15) . . ?
O1 C19 C18 126.10(15) . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl1 Cl1 Cl2A 107.6(4) 2_656 2_656 ?
Cl1 Cl1 C22 87.1(2) 2_656 . ?
Cl1 Cl1 C22 59.9(2) 2_656 2_656 ?
C22 Cl1 Cl2A 49.8(4) 2_656 2_656 ?
C22 Cl1 Cl2A 45.9(4) . 2_656 ?
C22 Cl1 C22 37.3(3) . 2_656 ?
C22 Cl2 C22 33.6(3) . 2_656 ?
C22 Cl2A Cl1 44.9(3) . 2_656 ?
C22 Cl2A Cl1 37.5(3) 2_656 2_656 ?
C22 Cl2A C22 33.6(3) 2_656 . ?
Cl1 C22 Cl1 32.99(17) . 2_656 ?
Cl1 C22 Cl2 109.6(3) . 2_656 ?
Cl1 C22 Cl2 109.4(3) 2_656 2_656 ?
Cl1 C22 Cl2 139.7(5) . . ?
Cl1 C22 Cl2A 85.3(6) 2_656 . ?
Cl1 C22 Cl2A 110.5(4) 2_656 2_656 ?
Cl1 C22 Cl2A 96.6(6) . 2_656 ?
Cl1 C22 Cl2A 116.5(7) . . ?
Cl1 C22 H22 97.0(17) . . ?
Cl1 C22 H22 121(2) 2_656 . ?
Cl2 C22 Cl1 110.6(5) . 2_656 ?
Cl2 C22 Cl2 98.3(4) . 2_656 ?
Cl2 C22 H22 94(3) . . ?
Cl2 C22 H22 119(3) 2_656 . ?
Cl2A C22 Cl2A 128.1(9) 2_656 . ?
Cl2A C22 H22 112(3) . . ?
Cl2A C22 H22 101(4) 2_656 . ?
C22 C22 Cl1 59.3(2) 2_656 2_656 ?
C22 C22 Cl1 83.4(2) 2_656 . ?
C22 C22 Cl2 85.9(6) 2_656 . ?
C22 C22 Cl2 60.6(5) 2_656 2_656 ?
C22 C22 Cl2A 78.8(6) 2_656 2_656 ?
C22 C22 Cl2A 67.6(6) 2_656 . ?
C22 C22 H22 179(3) 2_656 . ?

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
C1 C2 C3 C4 1.0(3) . . . . ?
C1 N2 C17 O2 29.28(17) . . . . ?
C1 N2 C17 C18 -93.54(14) . . . . ?
C1 C6 C7 C8 -140.07(15) . . . . ?
C1 C6 C7 C16 45.6(2) . . . . ?
F1 C2 C3 C4 -177.86(18) . . . . ?
N1 N2 C17 O2 155.69(12) . . . . ?
N1 N2 C17 C18 32.87(14) . . . . ?
C2 C1 N2 N1 -2.9(2) . . . . ?
C2 C1 N2 C17 114.88(17) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C2 C1 C6 C7 -175.12(14) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
N2 C1 C2 F1 -6.5(2) . . . . ?
N2 C1 C2 C3 174.61(17) . . . . ?
N2 C1 C6 C5 -176.31(14) . . . . ?
N2 C1 C6 C7 9.0(2) . . . . ?
N2 N1 C19 O1 -176.18(17) . . . . ?
N2 N1 C19 C18 4.6(2) . . . . ?
N2 C17 C18 C19 -30.21(15) . . . . ?
N2 C17 C18 C20 84.66(15) . . . . ?
N2 C17 C18 C21 -148.76(13) . . . . ?
O2 C17 C18 C19 -152.82(13) . . . . ?
O2 C17 C18 C20 -37.95(18) . . . . ?
O2 C17 C18 C21 88.63(16) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
C4 C5 C6 C7 176.33(17) . . . . ?
C5 C6 C7 C8 45.3(2) . . . . ?
C5 C6 C7 C16 -129.09(16) . . . . ?
C6 C1 C2 F1 177.98(14) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C1 N2 N1 172.55(12) . . . . ?
C6 C1 N2 C17 -69.67(17) . . . . ?
C6 C7 C8 C9 10.1(2) . . . . ?
C6 C7 C8 C13 -170.83(15) . . . . ?
C6 C7 C16 O2 -4.0(2) . . . . ?
C6 C7 C16 C15 170.58(15) . . . . ?
C7 C8 C9 C10 -179.51(18) . . . . ?
C7 C8 C13 C12 178.84(17) . . . . ?
C7 C8 C13 C14 -1.0(3) . . . . ?
C8 C7 C16 O2 -178.69(13) . . . . ?
C8 C7 C16 C15 -4.1(2) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C8 C13 C14 C15 -1.3(3) . . . . ?
C9 C8 C13 C12 -2.0(3) . . . . ?
C9 C8 C13 C14 178.14(18) . . . . ?
C9 C10 C11 C12 -1.5(4) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C8 1.0(3) . . . . ?
C11 C12 C13 C14 -179.2(2) . . . . ?
C12 C13 C14 C15 178.9(2) . . . . ?
C13 C8 C9 C10 1.4(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 O2 176.55(16) . . . . ?
C14 C15 C16 C7 1.8(3) . . . . ?
C16 O2 C17 N2 60.88(16) . . . . ?
C16 O2 C17 C18 -179.93(12) . . . . ?
C16 C7 C8 C9 -175.52(16) . . . . ?
C16 C7 C8 C13 3.6(2) . . . . ?
C17 O2 C16 C7 -76.57(17) . . . . ?
C17 O2 C16 C15 108.51(16) . . . . ?
C17 C18 C19 N1 16.24(17) . . . . ?
C17 C18 C19 O1 -163.00(18) . . . . ?
C19 N1 N2 C1 102.48(16) . . . . ?
C19 N1 N2 C17 -23.60(17) . . . . ?
C20 C18 C19 N1 -101.81(16) . . . . ?
C20 C18 C19 O1 79.0(2) . . . . ?
C21 C18 C19 N1 135.47(16) . . . . ?
C21 C18 C19 O1 -43.8(2) . . . . ?
Cl1 Cl1 C22 Cl2 -35.3(7) 2_656 . . . ?
Cl1 Cl1 C22 Cl2 95.7(5) 2_656 . . 2_656 ?
Cl1 Cl1 C22 Cl2A 118.1(5) 2_656 . . 2_656 ?
Cl1 Cl1 C22 Cl2A -20.7(4) 2_656 . . . ?
Cl1 Cl1 C22 C22 40.2(6) 2_656 . . 2_656 ?
Cl1 Cl2A C22 Cl1 11.1(2) 2_656 . . . ?
Cl1 Cl2A C22 Cl2A -112.5(7) 2_656 . . 2_656 ?
Cl1 Cl2A C22 C22 -58.7(3) 2_656 . . 2_656 ?
Cl2A Cl1 C22 Cl1 -118.1(5) 2_656 . . 2_656 ?
Cl2A Cl1 C22 Cl2A -138.8(5) 2_656 . . . ?
Cl2A Cl1 C22 C22 -77.8(7) 2_656 . . 2_656 ?
C22 Cl1 C22 Cl1 -40.2(6) 2_656 . . 2_656 ?
C22 Cl1 C22 Cl2 -75.6(8) 2_656 . . . ?
C22 Cl1 C22 Cl2 55.5(6) 2_656 . . 2_656 ?
C22 Cl1 C22 Cl2A 77.8(7) 2_656 . . 2_656 ?
C22 Cl1 C22 Cl2A -60.9(6) 2_656 . . . ?
C22 Cl2 C22 Cl1 74.7(6) 2_656 . . . ?
C22 Cl2 C22 Cl1 55.0(4) 2_656 . . 2_656 ?
C22 Cl2 C22 Cl2 -59.4(4) 2_656 . . 2_656 ?
C22 Cl2A C22 Cl1 69.8(4) 2_656 . . . ?
C22 Cl2A C22 Cl1 58.7(3) 2_656 . . 2_656 ?
C22 Cl2A C22 Cl2A -53.8(10) 2_656 . . 2_656 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_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 1.362
_oxdiff_exptl_absorpt_empirical_full_min 0.753
