# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_200715_s1_mj
_database_code_depnum_ccdc_archive 'CCDC 2033728'
loop_
_audit_author_name
_audit_author_address
'Bo Han'
;Chengdu University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2020-09-24 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2020-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H20 Cl F3 N2 O2'
_chemical_formula_sum            'C26 H20 Cl F3 N2 O2'
_chemical_formula_weight         484.89
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3cl1
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.1617(4)
_cell_length_b                   24.6313(11)
_cell_length_c                   11.5178(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.993(5)
_cell_angle_gamma                90
_cell_volume                     2314.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2740
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8360
_cell_measurement_theta_min      3.6290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10939
_diffrn_reflns_point_group_measured_fraction_full 0.746
_diffrn_reflns_point_group_measured_fraction_max 0.591
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.410
_diffrn_reflns_theta_min         2.995
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   13.00   1.0000    3.7500
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -99.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -12.00   88.00   1.0000    3.7500
omega____ theta____ kappa____ phi______ frames
    -       17.6648   19.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega    3.00   87.00   1.0000    3.7500
omega____ theta____ kappa____ phi______ frames
    -       17.6648   38.0000    0.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0129223000
_diffrn_orient_matrix_UB_12      0.0094782000
_diffrn_orient_matrix_UB_13      -0.0577496000
_diffrn_orient_matrix_UB_21      0.0842015000
_diffrn_orient_matrix_UB_22      0.0068463000
_diffrn_orient_matrix_UB_23      -0.0022510000
_diffrn_orient_matrix_UB_31      0.0172997000
_diffrn_orient_matrix_UB_32      -0.0263419000
_diffrn_orient_matrix_UB_33      -0.0213010000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.385
_reflns_Friedel_fraction_full    0.482
_reflns_Friedel_fraction_max     0.336
_reflns_number_gt                5383
_reflns_number_total             7552
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1392 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         7552
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.025
_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)+(0.0579P)²+0.0296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1220
_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), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C18(H18A,H18B), C20(H20A,H20B), C36(H36A,H36B), C44(H44A,
 H44B), C46(H46A,H46B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14), C16(H16), C17(H17),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C30(H30), C31(H31), C32(H32),
  C33(H33), C39(H39), C40(H40), C42(H42), C43(H43), C48(H48), C49(H49),
 C50(H50), C51(H51), C52(H52)
;
_atom_sites_solution_hydrogens   geom
_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
Cl1 Cl 0.3791(3) 0.76772(7) 0.47114(18) 0.1458(9) Uani 1 1 d . . . . .
F1 F 0.1415(6) 0.39459(15) 0.4487(3) 0.1249(14) Uani 1 1 d . . . . .
F2 F 0.3511(7) 0.36196(19) 0.5281(5) 0.1528(18) Uani 1 1 d . . . . .
F3 F 0.1181(8) 0.32412(15) 0.5482(4) 0.163(2) Uani 1 1 d . . . . .
O1 O -0.0577(4) 0.51540(13) 0.6488(3) 0.0647(8) Uani 1 1 d . . . . .
O2 O 0.4506(6) 0.4196(2) 0.7933(3) 0.1156(17) Uani 1 1 d . . . . .
N1 N 0.0244(3) 0.53157(13) 0.4636(3) 0.0416(7) Uani 1 1 d . . . . .
N2 N 0.2609(5) 0.45261(16) 0.6599(3) 0.0612(10) Uani 1 1 d . . . . .
C1 C 0.0459(5) 0.51651(16) 0.5757(3) 0.0458(9) Uani 1 1 d . . . . .
C2 C 0.2298(4) 0.50255(17) 0.5951(3) 0.0437(9) Uani 1 1 d . . . . .
C3 C 0.2888(4) 0.50242(15) 0.4742(3) 0.0387(8) Uani 1 1 d . . . . .
C4 C 0.4357(5) 0.48541(17) 0.4289(4) 0.0481(10) Uani 1 1 d . . . . .
H4 H 0.5179 0.4705 0.4771 0.058 Uiso 1 1 calc R . . . .
C5 C 0.4577(5) 0.49099(16) 0.3107(4) 0.0471(10) Uani 1 1 d . . . . .
H5 H 0.5549 0.4793 0.2791 0.057 Uiso 1 1 calc R . . . .
C6 C 0.3369(5) 0.51360(16) 0.2398(3) 0.0462(9) Uani 1 1 d . . . . .
H6 H 0.3558 0.5184 0.1613 0.055 Uiso 1 1 calc R . . . .
C7 C 0.1876(5) 0.52936(16) 0.2829(3) 0.0439(9) Uani 1 1 d . . . . .
H7 H 0.1051 0.5438 0.2344 0.053 Uiso 1 1 calc R . . . .
C8 C 0.1660(4) 0.52292(14) 0.3998(3) 0.0365(8) Uani 1 1 d . . . . .
C9 C 0.3089(5) 0.54589(19) 0.6797(4) 0.0553(11) Uani 1 1 d . . . . .
H9 H 0.2328 0.5505 0.7429 0.066 Uiso 1 1 calc R . . . .
C10 C 0.4552(6) 0.5139(3) 0.7305(4) 0.0830(17) Uani 1 1 d . . . . .
H10A H 0.5486 0.5169 0.6810 0.100 Uiso 1 1 calc R . . . .
H10B H 0.4866 0.5270 0.8075 0.100 Uiso 1 1 calc R . . . .
C11 C 0.3961(7) 0.4572(3) 0.7353(4) 0.0843(18) Uani 1 1 d . . . . .
C12 C 0.3362(5) 0.60119(19) 0.6305(4) 0.0525(11) Uani 1 1 d . . . . .
C13 C 0.2448(6) 0.6442(2) 0.6680(4) 0.0632(12) Uani 1 1 d . . . . .
H13 H 0.1697 0.6384 0.7256 0.076 Uiso 1 1 calc R . . . .
C14 C 0.2608(7) 0.6956(2) 0.6229(5) 0.0757(15) Uani 1 1 d . . . . .
H14 H 0.1996 0.7244 0.6509 0.091 Uiso 1 1 calc R . . . .
C15 C 0.3675(7) 0.7036(2) 0.5368(5) 0.0803(16) Uani 1 1 d . . . . .
C16 C 0.4626(8) 0.6627(3) 0.5001(6) 0.101(2) Uani 1 1 d . . . . .
H16 H 0.5380 0.6692 0.4430 0.121 Uiso 1 1 calc R . . . .
C17 C 0.4491(6) 0.6126(2) 0.5457(5) 0.0821(17) Uani 1 1 d . . . . .
H17 H 0.5166 0.5850 0.5200 0.099 Uiso 1 1 calc R . . . .
C18 C 0.1683(8) 0.4046(2) 0.6495(5) 0.0834(17) Uani 1 1 d . . . . .
H18A H 0.0532 0.4143 0.6509 0.100 Uiso 1 1 calc R . . . .
H18B H 0.1928 0.3824 0.7174 0.100 Uiso 1 1 calc R . . . .
C19 C 0.1931(10) 0.3711(2) 0.5452(6) 0.0939(19) Uani 1 1 d . . . . .
C20 C -0.1346(4) 0.54623(17) 0.4107(4) 0.0518(11) Uani 1 1 d . . . . .
H20A H -0.2181 0.5411 0.4676 0.062 Uiso 1 1 calc R . . . .
H20B H -0.1590 0.5217 0.3465 0.062 Uiso 1 1 calc R . . . .
C21 C -0.1446(4) 0.60357(16) 0.3666(3) 0.0440(9) Uani 1 1 d . . . . .
C22 C -0.0523(6) 0.64532(19) 0.4167(4) 0.0620(12) Uani 1 1 d . . . . .
H22 H 0.0230 0.6376 0.4768 0.074 Uiso 1 1 calc R . . . .
C23 C -0.0706(7) 0.6975(2) 0.3789(6) 0.0848(16) Uani 1 1 d . . . . .
H23 H -0.0095 0.7251 0.4144 0.102 Uiso 1 1 calc R . . . .
C24 C -0.1787(8) 0.7094(2) 0.2886(5) 0.0823(16) Uani 1 1 d . . . . .
H24 H -0.1910 0.7449 0.2624 0.099 Uiso 1 1 calc R . . . .
C25 C -0.2684(7) 0.6683(3) 0.2375(5) 0.0842(18) Uani 1 1 d . . . . .
H25 H -0.3422 0.6761 0.1764 0.101 Uiso 1 1 calc R . . . .
C26 C -0.2504(5) 0.6160(2) 0.2752(4) 0.0608(12) Uani 1 1 d . . . . .
H26 H -0.3106 0.5884 0.2386 0.073 Uiso 1 1 calc R . . . .
Cl2 Cl 1.1931(2) 0.15016(6) 0.26627(15) 0.0976(5) Uani 1 1 d . . . . .
F4 F 0.7065(4) 0.55453(12) -0.0470(3) 0.0922(10) Uani 1 1 d . . . . .
F5 F 0.6694(5) 0.48584(17) 0.0532(4) 0.1308(16) Uani 1 1 d . . . . .
F6 F 0.8841(5) 0.53150(19) 0.0810(3) 0.152(2) Uani 1 1 d . . . . .
O3 O 0.8630(4) 0.35250(12) -0.1928(2) 0.0610(8) Uani 1 1 d . . . . .
O4 O 1.2051(4) 0.49991(12) -0.0458(3) 0.0596(8) Uani 1 1 d . . . . .
N3 N 0.7130(4) 0.33486(13) -0.0326(3) 0.0445(8) Uani 1 1 d . . . . .
N4 N 0.9867(4) 0.44212(13) -0.0381(3) 0.0412(7) Uani 1 1 d . . . . .
C27 C 0.8392(5) 0.35640(16) -0.0901(4) 0.0452(9) Uani 1 1 d . . . . .
C28 C 0.9511(4) 0.38688(15) -0.0010(3) 0.0381(8) Uani 1 1 d . . . . .
C29 C 0.8590(4) 0.38138(15) 0.1091(3) 0.0386(8) Uani 1 1 d . . . . .
C30 C 0.8897(5) 0.40172(17) 0.2185(3) 0.0484(10) Uani 1 1 d . . . . .
H30 H 0.9802 0.4238 0.2340 0.058 Uiso 1 1 calc R . . . .
C31 C 0.7836(6) 0.3888(2) 0.3053(4) 0.0593(12) Uani 1 1 d . . . . .
H31 H 0.8030 0.4019 0.3802 0.071 Uiso 1 1 calc R . . . .
C32 C 0.6494(6) 0.3565(2) 0.2809(5) 0.0681(14) Uani 1 1 d . . . . .
H32 H 0.5786 0.3484 0.3400 0.082 Uiso 1 1 calc R . . . .
C33 C 0.6171(5) 0.33605(19) 0.1722(4) 0.0604(12) Uani 1 1 d . . . . .
H33 H 0.5263 0.3140 0.1569 0.072 Uiso 1 1 calc R . . . .
C34 C 0.7225(4) 0.34895(15) 0.0864(3) 0.0427(9) Uani 1 1 d . . . . .
C35 C 1.1245(4) 0.36046(15) 0.0018(3) 0.0411(9) Uani 1 1 d . . . . .
H35 H 1.1462 0.3503 -0.0785 0.049 Uiso 1 1 calc R . . . .
C36 C 1.2370(5) 0.40797(16) 0.0313(4) 0.0491(10) Uani 1 1 d . . . . .
H36A H 1.2523 0.4121 0.1148 0.059 Uiso 1 1 calc R . . . .
H36B H 1.3432 0.4032 -0.0026 0.059 Uiso 1 1 calc R . . . .
C37 C 1.1487(5) 0.45575(17) -0.0208(4) 0.0467(10) Uani 1 1 d . . . . .
C38 C 1.1407(4) 0.30903(15) 0.0728(3) 0.0405(9) Uani 1 1 d . . . . .
C39 C 1.1910(5) 0.30807(18) 0.1888(4) 0.0524(10) Uani 1 1 d . . . . .
H39 H 1.2164 0.3404 0.2269 0.063 Uiso 1 1 calc R . . . .
C40 C 1.2039(6) 0.2594(2) 0.2486(4) 0.0643(13) Uani 1 1 d . . . . .
H40 H 1.2372 0.2593 0.3267 0.077 Uiso 1 1 calc R . . . .
C41 C 1.1677(5) 0.2112(2) 0.1931(5) 0.0606(12) Uani 1 1 d . . . . .
C42 C 1.1138(6) 0.2110(2) 0.0808(5) 0.0670(13) Uani 1 1 d . . . . .
H42 H 1.0851 0.1784 0.0445 0.080 Uiso 1 1 calc R . . . .
C43 C 1.1012(5) 0.25990(17) 0.0195(4) 0.0564(11) Uani 1 1 d . . . . .
H43 H 1.0659 0.2596 -0.0581 0.068 Uiso 1 1 calc R . . . .
C44 C 0.8680(5) 0.47936(16) -0.0867(4) 0.0483(10) Uani 1 1 d . . . . .
H44A H 0.7848 0.4589 -0.1301 0.058 Uiso 1 1 calc R . . . .
H44B H 0.9217 0.5030 -0.1409 0.058 Uiso 1 1 calc R . . . .
C45 C 0.7869(6) 0.5133(2) 0.0004(4) 0.0658(13) Uani 1 1 d . . . . .
C46 C 0.5886(5) 0.30001(18) -0.0867(4) 0.0577(12) Uani 1 1 d . . . . .
H46A H 0.5787 0.3083 -0.1689 0.069 Uiso 1 1 calc R . . . .
H46B H 0.4838 0.3076 -0.0529 0.069 Uiso 1 1 calc R . . . .
C47 C 0.6273(5) 0.24070(16) -0.0717(4) 0.0495(10) Uani 1 1 d . . . . .
C48 C 0.7339(7) 0.21562(19) -0.1448(5) 0.0730(14) Uani 1 1 d . . . . .
H48 H 0.7786 0.2355 -0.2047 0.088 Uiso 1 1 calc R . . . .
C49 C 0.7748(8) 0.1625(3) -0.1312(7) 0.104(2) Uani 1 1 d . . . . .
H49 H 0.8458 0.1463 -0.1822 0.125 Uiso 1 1 calc R . . . .
C50 C 0.7123(10) 0.1329(2) -0.0431(7) 0.100(2) Uani 1 1 d . . . . .
H50 H 0.7422 0.0968 -0.0324 0.120 Uiso 1 1 calc R . . . .
C51 C 0.6037(9) 0.1574(2) 0.0301(5) 0.091(2) Uani 1 1 d . . . . .
H51 H 0.5583 0.1373 0.0893 0.110 Uiso 1 1 calc R . . . .
C52 C 0.5620(6) 0.2114(2) 0.0159(5) 0.0715(14) Uani 1 1 d . . . . .
H52 H 0.4897 0.2277 0.0659 0.086 Uiso 1 1 calc R . . . .


_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 C15 1.756(6) . ?
F1 C19 1.310(7) . ?
F2 C19 1.330(8) . ?
F3 C19 1.311(7) . ?
O1 C1 1.215(4) . ?
O2 C11 1.217(6) . ?
N1 C1 1.349(5) . ?
N1 C8 1.407(4) . ?
N1 C20 1.460(4) . ?
N2 C2 1.456(5) . ?
N2 C11 1.385(7) . ?
N2 C18 1.406(7) . ?
C1 C2 1.548(5) . ?
C2 C3 1.489(5) . ?
C2 C9 1.569(6) . ?
C3 C4 1.389(5) . ?
C3 C8 1.391(5) . ?
C4 C5 1.387(5) . ?
C5 C6 1.376(5) . ?
C6 C7 1.387(5) . ?
C7 C8 1.373(5) . ?
C9 C10 1.529(6) . ?
C9 C12 1.495(6) . ?
C10 C11 1.480(9) . ?
C12 C13 1.374(6) . ?
C12 C17 1.394(7) . ?
C13 C14 1.377(7) . ?
C14 C15 1.357(7) . ?
C15 C16 1.347(8) . ?
C16 C17 1.347(8) . ?
C18 C19 1.476(8) . ?
C20 C21 1.502(6) . ?
C21 C22 1.388(6) . ?
C21 C26 1.373(5) . ?
C22 C23 1.364(7) . ?
C23 C24 1.372(8) . ?
C24 C25 1.370(8) . ?
C25 C26 1.367(8) . ?
Cl2 C41 1.733(5) . ?
F4 C45 1.318(5) . ?
F5 C45 1.336(6) . ?
F6 C45 1.282(5) . ?
O3 C27 1.210(5) . ?
O4 C37 1.220(5) . ?
N3 C27 1.352(5) . ?
N3 C34 1.414(5) . ?
N3 C46 1.453(5) . ?
N4 C28 1.459(5) . ?
N4 C37 1.372(5) . ?
N4 C44 1.434(5) . ?
C27 C28 1.544(5) . ?
C28 C29 1.503(5) . ?
C28 C35 1.557(5) . ?
C29 C30 1.371(5) . ?
C29 C34 1.389(5) . ?
C30 C31 1.382(6) . ?
C31 C32 1.375(7) . ?
C32 C33 1.367(7) . ?
C33 C34 1.370(6) . ?
C35 C36 1.519(5) . ?
C35 C38 1.511(5) . ?
C36 C37 1.495(6) . ?
C38 C39 1.384(5) . ?
C38 C43 1.390(6) . ?
C39 C40 1.385(6) . ?
C40 C41 1.377(7) . ?
C41 C42 1.351(7) . ?
C42 C43 1.398(7) . ?
C44 C45 1.480(6) . ?
C46 C47 1.503(6) . ?
C47 C48 1.377(6) . ?
C47 C52 1.365(6) . ?
C48 C49 1.357(7) . ?
C49 C50 1.363(9) . ?
C50 C51 1.382(9) . ?
C51 C52 1.382(8) . ?

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
C1 N1 C8 112.1(3) . . ?
C1 N1 C20 123.5(3) . . ?
C8 N1 C20 123.6(3) . . ?
C11 N2 C2 111.9(4) . . ?
C11 N2 C18 122.4(4) . . ?
C18 N2 C2 125.7(4) . . ?
O1 C1 N1 126.8(4) . . ?
O1 C1 C2 126.2(4) . . ?
N1 C1 C2 107.0(3) . . ?
N2 C2 C1 114.3(3) . . ?
N2 C2 C3 114.9(3) . . ?
N2 C2 C9 101.3(3) . . ?
C1 C2 C9 108.3(3) . . ?
C3 C2 C1 102.0(3) . . ?
C3 C2 C9 116.3(3) . . ?
C4 C3 C2 131.5(3) . . ?
C4 C3 C8 119.4(3) . . ?
C8 C3 C2 109.0(3) . . ?
C5 C4 C3 118.8(4) . . ?
C6 C5 C4 120.6(4) . . ?
C5 C6 C7 121.4(4) . . ?
C8 C7 C6 117.6(3) . . ?
C3 C8 N1 108.7(3) . . ?
C7 C8 N1 129.1(3) . . ?
C7 C8 C3 122.2(3) . . ?
C10 C9 C2 100.7(4) . . ?
C12 C9 C2 116.6(3) . . ?
C12 C9 C10 119.3(4) . . ?
C11 C10 C9 104.4(4) . . ?
O2 C11 N2 123.4(7) . . ?
O2 C11 C10 128.7(6) . . ?
N2 C11 C10 107.9(4) . . ?
C13 C12 C9 119.6(4) . . ?
C13 C12 C17 116.3(5) . . ?
C17 C12 C9 124.1(4) . . ?
C12 C13 C14 122.1(5) . . ?
C15 C14 C13 118.7(5) . . ?
C14 C15 Cl1 119.3(5) . . ?
C16 C15 Cl1 119.8(5) . . ?
C16 C15 C14 120.9(6) . . ?
C17 C16 C15 120.4(5) . . ?
C16 C17 C12 121.5(5) . . ?
N2 C18 C19 116.8(5) . . ?
F1 C19 F2 103.5(6) . . ?
F1 C19 F3 106.0(6) . . ?
F1 C19 C18 113.3(5) . . ?
F2 C19 C18 112.1(6) . . ?
F3 C19 F2 108.0(6) . . ?
F3 C19 C18 113.2(5) . . ?
N1 C20 C21 114.3(3) . . ?
C22 C21 C20 122.3(4) . . ?
C26 C21 C20 119.6(4) . . ?
C26 C21 C22 118.1(4) . . ?
C23 C22 C21 120.9(5) . . ?
C22 C23 C24 120.2(6) . . ?
C25 C24 C23 119.2(5) . . ?
C26 C25 C24 120.7(5) . . ?
C25 C26 C21 120.7(5) . . ?
C27 N3 C34 111.2(3) . . ?
C27 N3 C46 123.7(3) . . ?
C34 N3 C46 125.1(3) . . ?
C37 N4 C28 112.7(3) . . ?
C37 N4 C44 122.3(3) . . ?
C44 N4 C28 124.9(3) . . ?
O3 C27 N3 126.8(4) . . ?
O3 C27 C28 125.2(4) . . ?
N3 C27 C28 108.0(3) . . ?
N4 C28 C27 112.2(3) . . ?
N4 C28 C29 116.2(3) . . ?
N4 C28 C35 101.9(3) . . ?
C27 C28 C35 109.1(3) . . ?
C29 C28 C27 102.4(3) . . ?
C29 C28 C35 115.2(3) . . ?
C30 C29 C28 131.5(3) . . ?
C30 C29 C34 120.2(3) . . ?
C34 C29 C28 108.3(3) . . ?
C29 C30 C31 118.8(4) . . ?
C32 C31 C30 120.0(4) . . ?
C33 C32 C31 121.8(4) . . ?
C32 C33 C34 118.0(4) . . ?
C29 C34 N3 109.9(3) . . ?
C33 C34 N3 128.9(4) . . ?
C33 C34 C29 121.2(4) . . ?
C36 C35 C28 103.0(3) . . ?
C38 C35 C28 115.1(3) . . ?
C38 C35 C36 118.9(3) . . ?
C37 C36 C35 103.7(3) . . ?
O4 C37 N4 123.6(4) . . ?
O4 C37 C36 128.0(4) . . ?
N4 C37 C36 108.4(3) . . ?
C39 C38 C35 123.7(4) . . ?
C39 C38 C43 117.9(4) . . ?
C43 C38 C35 118.5(4) . . ?
C38 C39 C40 120.7(4) . . ?
C41 C40 C39 120.2(4) . . ?
C40 C41 Cl2 120.1(4) . . ?
C42 C41 Cl2 119.5(4) . . ?
C42 C41 C40 120.4(4) . . ?
C41 C42 C43 119.7(5) . . ?
C38 C43 C42 121.1(4) . . ?
N4 C44 C45 114.2(3) . . ?
F4 C45 F5 103.0(4) . . ?
F4 C45 C44 112.5(4) . . ?
F5 C45 C44 111.6(4) . . ?
F6 C45 F4 108.5(4) . . ?
F6 C45 F5 106.5(5) . . ?
F6 C45 C44 114.1(4) . . ?
N3 C46 C47 112.6(3) . . ?
C48 C47 C46 120.0(4) . . ?
C52 C47 C46 120.9(4) . . ?
C52 C47 C48 119.1(4) . . ?
C49 C48 C47 121.3(5) . . ?
C48 C49 C50 120.3(6) . . ?
C49 C50 C51 119.0(5) . . ?
C52 C51 C50 120.5(6) . . ?
C47 C52 C51 119.7(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
