# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_3na
_database_code_depnum_ccdc_archive 'CCDC 2250260'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-17
_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         '2(C22 H16 F N3 O2)'
_chemical_formula_sum            'C44 H32 F2 N6 O4'
_chemical_formula_weight         746.75
_chemical_absolute_configuration ?
_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'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   18.2786(2)
_cell_length_b                   11.9317(2)
_cell_length_c                   16.8004(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3664.08(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8355
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2570
_cell_measurement_theta_min      4.3900
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.858
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13760
_diffrn_reflns_point_group_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         4.425
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_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    -54.00 -28.00   1.00    1.34    --  -35.62 159.00  17.00   26
  2  ω    -22.00  34.00   1.00    1.34    --   35.62 -10.00 -74.00   56
  3  ω    113.00 141.00   1.00    5.36    --  107.12 138.00 122.00   28
  4  ω     48.00 145.00   1.00    5.36    --  107.12 -10.00 -74.00   97
  5  ω    110.00 174.00   1.00    5.36    --  107.12 118.00-135.00   64
  6  ω    -81.00 -23.00   1.00    1.34    --  -35.62 -57.00  60.00   58
  7  ω     41.00  74.00   1.00    1.34    --   35.62 -99.00 -60.00   33
  8  ω    -17.00  62.00   1.00    1.34    --   35.62 -77.00 -60.00   79
  9  ω     40.00  98.00   1.00    5.36    --  107.12 -95.00-180.00   58
 10  ω     55.00 119.00   1.00    5.36    --  107.12 -45.00-120.00   64
 11  ω     74.00 103.00   1.00    5.36    --  107.12 -95.00-150.00   29
 12  ω    105.00 157.00   1.00    5.36    --  107.12 111.00   0.00   52
 13  ω     28.00  53.00   1.00    1.34    --   35.87-118.00 138.00   25
 14  ω    -65.00 -40.00   1.00    1.34    --  -35.87 118.00-135.00   25
 15  ω   -103.00 -60.00   1.00    1.34    --  -35.87 -57.00-120.00   43
 16  ω   -103.00 -19.00   1.00    1.34    --  -35.87 -57.00 -30.00   84
 17  ω    -91.00 -66.00   1.00    1.34    --  -35.87 159.00  17.00   25
 18  ω   -103.00 -64.00   1.00    1.34    --  -35.87 -57.00 150.00   39
 19  ω    -53.00  31.00   1.00    1.34    --  -35.87  57.00-120.00   84
;
_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      -0.0112946000
_diffrn_orient_matrix_UB_12      0.1278659000
_diffrn_orient_matrix_UB_13      -0.0030018000
_diffrn_orient_matrix_UB_21      -0.0023980000
_diffrn_orient_matrix_UB_22      0.0037723000
_diffrn_orient_matrix_UB_23      0.0916307000
_diffrn_orient_matrix_UB_31      0.0834887000
_diffrn_orient_matrix_UB_32      0.0174151000
_diffrn_orient_matrix_UB_33      0.0022308000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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         0.652
_reflns_Friedel_fraction_full    0.702
_reflns_Friedel_fraction_max     0.702
_reflns_number_gt                5287
_reflns_number_total             5541
_reflns_odcompleteness_completeness 99.92
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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         0.446
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.40(12)
_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     509
_refine_ls_number_reflns         5541
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.047
_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)+(0.0868P)²+0.7611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1316
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), N4(H4A), C24(H24), C25(H25), C26(H26),
 C27(H27), C33(H33), C34(H34), C35(H35), C38(H38), C39(H39), C40(H40), C41(H41)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C44(H44A,H44B,H44C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_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
F1 F 0.85134(13) 0.8665(2) 0.79666(15) 0.0491(6) Uani 1 1 d . . . . .
O1 O 0.87755(13) 0.7224(2) 0.53733(16) 0.0368(6) Uani 1 1 d . . . . .
H1 H 0.909337 0.701310 0.506315 0.055 Uiso 1 1 calc R U . . .
O2 O 0.75833(16) 0.6786(3) 0.79807(17) 0.0431(7) Uani 1 1 d . . . . .
N1 N 0.80343(16) 0.5556(2) 0.6476(2) 0.0324(7) Uani 1 1 d . . . . .
H1A H 0.836991 0.552846 0.683456 0.039 Uiso 1 1 calc R U . . .
N2 N 0.71591(15) 0.6260(3) 0.57049(19) 0.0284(6) Uani 1 1 d . . . . .
N3 N 0.68798(16) 0.8236(3) 0.7512(2) 0.0360(7) Uani 1 1 d . . . . .
C1 C 0.77792(19) 0.4659(3) 0.6030(2) 0.0306(7) Uani 1 1 d . . . . .
C2 C 0.7981(2) 0.3545(3) 0.6003(3) 0.0428(10) Uani 1 1 d . . . . .
H2 H 0.833873 0.325720 0.633906 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7629(3) 0.2884(3) 0.5460(3) 0.0505(11) Uani 1 1 d . . . . .
H3 H 0.774989 0.212860 0.542608 0.061 Uiso 1 1 calc R U . . .
C4 C 0.7094(3) 0.3315(4) 0.4958(3) 0.0527(12) Uani 1 1 d . . . . .
H4 H 0.687339 0.284332 0.458886 0.063 Uiso 1 1 calc R U . . .
C5 C 0.6882(2) 0.4428(4) 0.4994(3) 0.0432(10) Uani 1 1 d . . . . .
H5 H 0.652002 0.470952 0.466067 0.052 Uiso 1 1 calc R U . . .
C6 C 0.72339(19) 0.5108(3) 0.5548(2) 0.0315(8) Uani 1 1 d . . . . .
C7 C 0.76618(17) 0.6478(3) 0.6248(2) 0.0243(7) Uani 1 1 d . . . . .
C8 C 0.78045(16) 0.7592(3) 0.6641(2) 0.0231(7) Uani 1 1 d . . . . .
C9 C 0.86249(16) 0.7835(3) 0.6694(2) 0.0247(7) Uani 1 1 d . . . . .
C10 C 0.89460(19) 0.8331(3) 0.7352(2) 0.0312(8) Uani 1 1 d . . . . .
C11 C 0.9693(2) 0.8514(4) 0.7429(3) 0.0449(10) Uani 1 1 d . . . . .
H11 H 0.988828 0.883498 0.788641 0.054 Uiso 1 1 calc R U . . .
C12 C 1.0135(2) 0.8202(4) 0.6803(3) 0.0461(10) Uani 1 1 d . . . . .
H12 H 1.063809 0.830257 0.684248 0.055 Uiso 1 1 calc R U . . .
C13 C 0.98468(19) 0.7746(4) 0.6121(3) 0.0378(9) Uani 1 1 d . . . . .
H13 H 1.015537 0.754013 0.570613 0.045 Uiso 1 1 calc R U . . .
C14 C 0.90893(18) 0.7588(3) 0.6048(2) 0.0285(7) Uani 1 1 d . . . . .
C15 C 0.73647(17) 0.8535(3) 0.6264(2) 0.0270(7) Uani 1 1 d . . . . .
C16 C 0.7437(2) 0.9067(3) 0.5543(2) 0.0337(8) Uani 1 1 d . . . . .
H16 H 0.780343 0.886149 0.518720 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6948(2) 0.9919(3) 0.5359(3) 0.0463(10) Uani 1 1 d . . . . .
H17 H 0.698303 1.028524 0.487215 0.056 Uiso 1 1 calc R U . . .
C18 C 0.6408(2) 1.0229(4) 0.5895(3) 0.0522(12) Uani 1 1 d . . . . .
H18 H 0.607945 1.079055 0.575599 0.063 Uiso 1 1 calc R U . . .
C19 C 0.6348(2) 0.9725(4) 0.6627(3) 0.0479(11) Uani 1 1 d . . . . .
H19 H 0.599309 0.995109 0.698972 0.057 Uiso 1 1 calc R U . . .
C20 C 0.68285(18) 0.8872(3) 0.6806(2) 0.0328(8) Uani 1 1 d . . . . .
C21 C 0.74338(18) 0.7469(3) 0.7477(2) 0.0296(7) Uani 1 1 d . . . . .
C22 C 0.6431(3) 0.8403(5) 0.8216(3) 0.0560(12) Uani 1 1 d . . . . .
H22A H 0.593493 0.819250 0.810104 0.084 Uiso 1 1 calc R U . . .
H22B H 0.644588 0.917800 0.836902 0.084 Uiso 1 1 calc R U . . .
H22C H 0.661450 0.794907 0.864341 0.084 Uiso 1 1 calc R U . . .
F2 F 0.59717(17) 0.6245(3) 0.19310(15) 0.0609(8) Uani 1 1 d . . . . .
O3 O 0.63218(15) 0.7289(3) 0.46080(16) 0.0399(6) Uani 1 1 d . . . . .
H3A H 0.661093 0.713802 0.496559 0.060 Uiso 1 1 calc R U . . .
O4 O 0.5067(2) 0.8119(3) 0.2067(2) 0.0646(10) Uani 1 1 d . . . . .
N4 N 0.56750(17) 0.9175(3) 0.3583(2) 0.0337(7) Uani 1 1 d . . . . .
H4A H 0.604198 0.915426 0.326347 0.040 Uiso 1 1 calc R U . . .
N5 N 0.47157(16) 0.8584(2) 0.42833(19) 0.0305(6) Uani 1 1 d . . . . .
N6 N 0.4366(2) 0.6656(4) 0.2492(3) 0.0565(11) Uani 1 1 d . . . . .
C23 C 0.54267(18) 1.0103(3) 0.3984(2) 0.0302(7) Uani 1 1 d . . . . .
C24 C 0.5654(2) 1.1216(3) 0.3990(3) 0.0395(9) Uani 1 1 d . . . . .
H24 H 0.604456 1.146129 0.368174 0.047 Uiso 1 1 calc R U . . .
C25 C 0.5270(2) 1.1933(3) 0.4475(3) 0.0459(10) Uani 1 1 d . . . . .
H25 H 0.540722 1.268322 0.449719 0.055 Uiso 1 1 calc R U . . .
C26 C 0.4679(2) 1.1569(3) 0.4936(3) 0.0453(10) Uani 1 1 d . . . . .
H26 H 0.443571 1.207639 0.526189 0.054 Uiso 1 1 calc R U . . .
C27 C 0.4452(2) 1.0466(4) 0.4913(3) 0.0436(10) Uani 1 1 d . . . . .
H27 H 0.405672 1.022635 0.521754 0.052 Uiso 1 1 calc R U . . .
C28 C 0.48258(19) 0.9726(3) 0.4426(2) 0.0293(7) Uani 1 1 d . . . . .
C29 C 0.52411(18) 0.8298(3) 0.3780(2) 0.0275(7) Uani 1 1 d . . . . .
C30 C 0.53173(19) 0.7189(3) 0.3365(2) 0.0305(8) Uani 1 1 d . . . . .
C31 C 0.6123(2) 0.6878(3) 0.3250(2) 0.0292(7) Uani 1 1 d . . . . .
C32 C 0.6417(2) 0.6465(3) 0.2550(2) 0.0392(9) Uani 1 1 d . . . . .
C33 C 0.7153(3) 0.6233(4) 0.2441(3) 0.0515(11) Uani 1 1 d . . . . .
H33 H 0.732854 0.596851 0.195700 0.062 Uiso 1 1 calc R U . . .
C34 C 0.7612(2) 0.6409(4) 0.3074(3) 0.0535(12) Uani 1 1 d . . . . .
H34 H 0.810996 0.627331 0.301435 0.064 Uiso 1 1 calc R U . . .
C35 C 0.7355(2) 0.6781(4) 0.3792(3) 0.0451(10) Uani 1 1 d . . . . .
H35 H 0.767826 0.689855 0.421109 0.054 Uiso 1 1 calc R U . . .
C36 C 0.6612(2) 0.6983(3) 0.3899(2) 0.0331(8) Uani 1 1 d . . . . .
C37 C 0.4859(2) 0.6259(3) 0.3721(3) 0.0343(8) Uani 1 1 d . . . . .
C38 C 0.4908(2) 0.5689(3) 0.4426(3) 0.0458(10) Uani 1 1 d . . . . .
H38 H 0.527978 0.585210 0.478557 0.055 Uiso 1 1 calc R U . . .
C39 C 0.4396(3) 0.4862(4) 0.4597(4) 0.0663(16) Uani 1 1 d . . . . .
H39 H 0.441657 0.448572 0.508097 0.080 Uiso 1 1 calc R U . . .
C40 C 0.3858(3) 0.4597(5) 0.4057(5) 0.080(2) Uani 1 1 d . . . . .
H40 H 0.351972 0.404168 0.418172 0.096 Uiso 1 1 calc R U . . .
C41 C 0.3810(3) 0.5138(5) 0.3331(5) 0.075(2) Uani 1 1 d . . . . .
H41 H 0.345243 0.494702 0.296091 0.090 Uiso 1 1 calc R U . . .
C42 C 0.4313(2) 0.5973(4) 0.3175(3) 0.0484(11) Uani 1 1 d . . . . .
C43 C 0.4921(2) 0.7400(4) 0.2551(3) 0.0407(9) Uani 1 1 d . . . . .
C44 C 0.3898(4) 0.6586(7) 0.1797(4) 0.101(3) Uani 1 1 d . . . . .
H44A H 0.401446 0.592123 0.150060 0.151 Uiso 1 1 calc R U . . .
H44B H 0.397352 0.723274 0.146691 0.151 Uiso 1 1 calc R U . . .
H44C H 0.339543 0.655750 0.196203 0.151 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
F1 C10 1.360(4) . ?
O1 H1 0.8200 . ?
O1 C14 1.343(4) . ?
O2 C21 1.206(5) . ?
N1 H1A 0.8600 . ?
N1 C1 1.387(5) . ?
N1 C7 1.350(4) . ?
N2 C6 1.405(5) . ?
N2 C7 1.321(4) . ?
N3 C20 1.412(5) . ?
N3 C21 1.366(5) . ?
N3 C22 1.454(5) . ?
C1 C2 1.380(5) . ?
C1 C6 1.391(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(5) . ?
C7 C8 1.507(4) . ?
C8 C9 1.530(4) . ?
C8 C15 1.520(4) . ?
C8 C21 1.567(5) . ?
C9 C10 1.384(5) . ?
C9 C14 1.409(5) . ?
C10 C11 1.389(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.403(5) . ?
C15 C16 1.374(6) . ?
C15 C20 1.397(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
F2 C32 1.347(5) . ?
O3 H3A 0.8200 . ?
O3 C36 1.353(5) . ?
O4 C43 1.212(6) . ?
N4 H4A 0.8600 . ?
N4 C23 1.373(5) . ?
N4 C29 1.354(5) . ?
N5 C28 1.398(4) . ?
N5 C29 1.324(5) . ?
N6 C42 1.411(7) . ?
N6 C43 1.351(6) . ?
N6 C44 1.452(6) . ?
C23 C24 1.391(5) . ?
C23 C28 1.400(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.374(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.398(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.380(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.384(5) . ?
C29 C30 1.503(5) . ?
C30 C31 1.531(5) . ?
C30 C37 1.513(5) . ?
C30 C43 1.567(5) . ?
C31 C32 1.383(5) . ?
C31 C36 1.416(5) . ?
C32 C33 1.384(6) . ?
C33 H33 0.9300 . ?
C33 C34 1.371(8) . ?
C34 H34 0.9300 . ?
C34 C35 1.369(7) . ?
C35 H35 0.9300 . ?
C35 C36 1.391(5) . ?
C37 C38 1.368(6) . ?
C37 C42 1.398(6) . ?
C38 H38 0.9300 . ?
C38 C39 1.391(6) . ?
C39 H39 0.9300 . ?
C39 C40 1.375(10) . ?
C40 H40 0.9300 . ?
C40 C41 1.383(10) . ?
C41 H41 0.9300 . ?
C41 C42 1.380(7) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?

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
C14 O1 H1 109.5 . . ?
C1 N1 H1A 126.1 . . ?
C7 N1 H1A 126.1 . . ?
C7 N1 C1 107.8(3) . . ?
C7 N2 C6 104.8(3) . . ?
C20 N3 C22 124.9(3) . . ?
C21 N3 C20 111.9(3) . . ?
C21 N3 C22 123.0(4) . . ?
N1 C1 C6 105.0(3) . . ?
C2 C1 N1 132.1(4) . . ?
C2 C1 C6 122.9(4) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 C1 116.9(4) . . ?
C3 C2 H2 121.6 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(4) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.7(4) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 121.3 . . ?
C4 C5 C6 117.3(4) . . ?
C6 C5 H5 121.3 . . ?
C1 C6 N2 109.7(3) . . ?
C1 C6 C5 119.7(4) . . ?
C5 C6 N2 130.6(4) . . ?
N1 C7 C8 120.5(3) . . ?
N2 C7 N1 112.7(3) . . ?
N2 C7 C8 126.6(3) . . ?
C7 C8 C9 111.2(3) . . ?
C7 C8 C15 112.2(3) . . ?
C7 C8 C21 103.6(3) . . ?
C9 C8 C21 112.9(3) . . ?
C15 C8 C9 113.7(3) . . ?
C15 C8 C21 102.4(3) . . ?
C10 C9 C8 122.9(3) . . ?
C10 C9 C14 116.7(3) . . ?
C14 C9 C8 120.4(3) . . ?
F1 C10 C9 119.0(3) . . ?
F1 C10 C11 117.1(3) . . ?
C9 C10 C11 123.9(4) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 C10 117.6(4) . . ?
C12 C11 H11 121.2 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.3(4) . . ?
C14 C13 H13 119.8 . . ?
O1 C14 C9 117.4(3) . . ?
O1 C14 C13 122.6(3) . . ?
C13 C14 C9 120.0(3) . . ?
C16 C15 C8 131.1(3) . . ?
C16 C15 C20 120.6(3) . . ?
C20 C15 C8 108.2(3) . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.2(4) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(4) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.5(4) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 121.1 . . ?
C18 C19 C20 117.9(4) . . ?
C20 C19 H19 121.1 . . ?
C15 C20 N3 110.2(3) . . ?
C19 C20 N3 128.5(4) . . ?
C19 C20 C15 121.2(4) . . ?
O2 C21 N3 126.2(3) . . ?
O2 C21 C8 126.5(3) . . ?
N3 C21 C8 107.2(3) . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C36 O3 H3A 109.5 . . ?
C23 N4 H4A 126.0 . . ?
C29 N4 H4A 126.0 . . ?
C29 N4 C23 108.0(3) . . ?
C29 N5 C28 104.8(3) . . ?
C42 N6 C44 125.5(5) . . ?
C43 N6 C42 111.8(4) . . ?
C43 N6 C44 122.7(5) . . ?
N4 C23 C24 132.4(3) . . ?
N4 C23 C28 105.1(3) . . ?
C24 C23 C28 122.4(3) . . ?
C23 C24 H24 121.7 . . ?
C25 C24 C23 116.5(4) . . ?
C25 C24 H24 121.7 . . ?
C24 C25 H25 119.0 . . ?
C24 C25 C26 121.9(4) . . ?
C26 C25 H25 119.0 . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 120.9(4) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 120.8 . . ?
C26 C27 C28 118.4(4) . . ?
C28 C27 H27 120.8 . . ?
N5 C28 C23 109.6(3) . . ?
C27 C28 N5 130.7(4) . . ?
C27 C28 C23 119.8(3) . . ?
N4 C29 C30 120.8(3) . . ?
N5 C29 N4 112.5(3) . . ?
N5 C29 C30 126.2(3) . . ?
C29 C30 C31 111.2(3) . . ?
C29 C30 C37 114.2(3) . . ?
C29 C30 C43 102.8(3) . . ?
C31 C30 C43 111.9(3) . . ?
C37 C30 C31 113.8(3) . . ?
C37 C30 C43 102.0(3) . . ?
C32 C31 C30 124.6(3) . . ?
C32 C31 C36 116.2(3) . . ?
C36 C31 C30 119.2(3) . . ?
F2 C32 C31 119.4(4) . . ?
F2 C32 C33 116.5(4) . . ?
C31 C32 C33 124.1(4) . . ?
C32 C33 H33 121.3 . . ?
C34 C33 C32 117.5(4) . . ?
C34 C33 H33 121.3 . . ?
C33 C34 H34 119.2 . . ?
C35 C34 C33 121.5(4) . . ?
C35 C34 H34 119.2 . . ?
C34 C35 H35 119.8 . . ?
C34 C35 C36 120.4(4) . . ?
C36 C35 H35 119.8 . . ?
O3 C36 C31 117.1(3) . . ?
O3 C36 C35 122.9(4) . . ?
C35 C36 C31 120.1(4) . . ?
C38 C37 C30 132.1(4) . . ?
C38 C37 C42 119.5(4) . . ?
C42 C37 C30 108.3(4) . . ?
C37 C38 H38 120.4 . . ?
C37 C38 C39 119.2(5) . . ?
C39 C38 H38 120.4 . . ?
C38 C39 H39 119.7 . . ?
C40 C39 C38 120.6(6) . . ?
C40 C39 H39 119.7 . . ?
C39 C40 H40 119.3 . . ?
C39 C40 C41 121.3(5) . . ?
C41 C40 H40 119.3 . . ?
C40 C41 H41 121.3 . . ?
C42 C41 C40 117.5(5) . . ?
C42 C41 H41 121.3 . . ?
C37 C42 N6 110.1(4) . . ?
C41 C42 N6 128.1(5) . . ?
C41 C42 C37 121.9(6) . . ?
O4 C43 N6 125.5(4) . . ?
O4 C43 C30 126.7(4) . . ?
N6 C43 C30 107.8(4) . . ?
N6 C44 H44A 109.5 . . ?
N6 C44 H44B 109.5 . . ?
N6 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

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
F1 C10 C11 C12 -178.6(4) . . . . ?
N1 C1 C2 C3 -177.4(4) . . . . ?
N1 C1 C6 N2 -0.3(4) . . . . ?
N1 C1 C6 C5 177.2(3) . . . . ?
N1 C7 C8 C9 47.7(4) . . . . ?
N1 C7 C8 C15 176.4(3) . . . . ?
N1 C7 C8 C21 -73.9(4) . . . . ?
N2 C7 C8 C9 -136.6(3) . . . . ?
N2 C7 C8 C15 -7.9(5) . . . . ?
N2 C7 C8 C21 101.8(4) . . . . ?
C1 N1 C7 N2 2.4(4) . . . . ?
C1 N1 C7 C8 178.6(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C1 C6 N2 -179.4(4) . . . . ?
C2 C1 C6 C5 -2.0(6) . . . . ?
C2 C3 C4 C5 -1.3(7) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 N2 177.6(4) . . . . ?
C4 C5 C6 C1 0.7(6) . . . . ?
C6 N2 C7 N1 -2.4(4) . . . . ?
C6 N2 C7 C8 -178.4(3) . . . . ?
C6 C1 C2 C3 1.5(6) . . . . ?
C7 N1 C1 C2 177.9(4) . . . . ?
C7 N1 C1 C6 -1.2(4) . . . . ?
C7 N2 C6 C1 1.6(4) . . . . ?
C7 N2 C6 C5 -175.5(4) . . . . ?
C7 C8 C9 C10 -140.4(3) . . . . ?
C7 C8 C9 C14 41.7(4) . . . . ?
C7 C8 C15 C16 -72.4(4) . . . . ?
C7 C8 C15 C20 109.9(3) . . . . ?
C7 C8 C21 O2 60.1(4) . . . . ?
C7 C8 C21 N3 -116.3(3) . . . . ?
C8 C9 C10 F1 -3.0(5) . . . . ?
C8 C9 C10 C11 177.0(4) . . . . ?
C8 C9 C14 O1 5.3(5) . . . . ?
C8 C9 C14 C13 -175.9(3) . . . . ?
C8 C15 C16 C17 -179.6(3) . . . . ?
C8 C15 C20 N3 0.4(4) . . . . ?
C8 C15 C20 C19 179.6(3) . . . . ?
C9 C8 C15 C16 55.0(5) . . . . ?
C9 C8 C15 C20 -122.6(3) . . . . ?
C9 C8 C21 O2 -60.3(5) . . . . ?
C9 C8 C21 N3 123.2(3) . . . . ?
C9 C10 C11 C12 1.4(6) . . . . ?
C10 C9 C14 O1 -172.7(3) . . . . ?
C10 C9 C14 C13 6.1(5) . . . . ?
C10 C11 C12 C13 1.2(7) . . . . ?
C11 C12 C13 C14 0.1(7) . . . . ?
C12 C13 C14 O1 174.9(4) . . . . ?
C12 C13 C14 C9 -3.9(6) . . . . ?
C14 C9 C10 F1 175.0(3) . . . . ?
C14 C9 C10 C11 -5.0(6) . . . . ?
C15 C8 C9 C10 91.6(4) . . . . ?
C15 C8 C9 C14 -86.3(4) . . . . ?
C15 C8 C21 O2 177.0(4) . . . . ?
C15 C8 C21 N3 0.5(3) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
C16 C15 C20 N3 -177.6(3) . . . . ?
C16 C15 C20 C19 1.6(5) . . . . ?
C16 C17 C18 C19 1.4(6) . . . . ?
C17 C18 C19 C20 -1.9(6) . . . . ?
C18 C19 C20 N3 179.5(4) . . . . ?
C18 C19 C20 C15 0.4(6) . . . . ?
C20 N3 C21 O2 -176.8(4) . . . . ?
C20 N3 C21 C8 -0.3(4) . . . . ?
C20 C15 C16 C17 -2.1(5) . . . . ?
C21 N3 C20 C15 0.0(4) . . . . ?
C21 N3 C20 C19 -179.2(4) . . . . ?
C21 C8 C9 C10 -24.5(4) . . . . ?
C21 C8 C9 C14 157.6(3) . . . . ?
C21 C8 C15 C16 177.2(3) . . . . ?
C21 C8 C15 C20 -0.5(3) . . . . ?
C22 N3 C20 C15 176.8(4) . . . . ?
C22 N3 C20 C19 -2.4(6) . . . . ?
C22 N3 C21 O2 6.4(6) . . . . ?
C22 N3 C21 C8 -177.2(3) . . . . ?
F2 C32 C33 C34 -177.5(4) . . . . ?
N4 C23 C24 C25 -179.9(4) . . . . ?
N4 C23 C28 N5 -0.4(4) . . . . ?
N4 C23 C28 C27 179.0(4) . . . . ?
N4 C29 C30 C31 42.3(5) . . . . ?
N4 C29 C30 C37 172.8(3) . . . . ?
N4 C29 C30 C43 -77.6(4) . . . . ?
N5 C29 C30 C31 -146.5(3) . . . . ?
N5 C29 C30 C37 -16.0(5) . . . . ?
N5 C29 C30 C43 93.6(4) . . . . ?
C23 N4 C29 N5 0.4(4) . . . . ?
C23 N4 C29 C30 172.8(3) . . . . ?
C23 C24 C25 C26 -0.4(7) . . . . ?
C24 C23 C28 N5 178.2(4) . . . . ?
C24 C23 C28 C27 -2.4(6) . . . . ?
C24 C25 C26 C27 -0.8(7) . . . . ?
C25 C26 C27 C28 0.4(7) . . . . ?
C26 C27 C28 N5 -179.5(4) . . . . ?
C26 C27 C28 C23 1.1(6) . . . . ?
C28 N5 C29 N4 -0.6(4) . . . . ?
C28 N5 C29 C30 -172.5(3) . . . . ?
C28 C23 C24 C25 2.0(6) . . . . ?
C29 N4 C23 C24 -178.3(4) . . . . ?
C29 N4 C23 C28 0.0(4) . . . . ?
C29 N5 C28 C23 0.7(4) . . . . ?
C29 N5 C28 C27 -178.7(4) . . . . ?
C29 C30 C31 C32 -134.6(4) . . . . ?
C29 C30 C31 C36 47.1(5) . . . . ?
C29 C30 C37 C38 -69.8(5) . . . . ?
C29 C30 C37 C42 112.0(4) . . . . ?
C29 C30 C43 O4 57.2(5) . . . . ?
C29 C30 C43 N6 -120.8(4) . . . . ?
C30 C31 C32 F2 -4.4(6) . . . . ?
C30 C31 C32 C33 177.0(4) . . . . ?
C30 C31 C36 O3 4.3(5) . . . . ?
C30 C31 C36 C35 -175.5(4) . . . . ?
C30 C37 C38 C39 179.6(4) . . . . ?
C30 C37 C42 N6 -1.0(5) . . . . ?
C30 C37 C42 C41 179.4(4) . . . . ?
C31 C30 C37 C38 59.4(5) . . . . ?
C31 C30 C37 C42 -118.8(4) . . . . ?
C31 C30 C43 O4 -62.1(6) . . . . ?
C31 C30 C43 N6 119.8(4) . . . . ?
C31 C32 C33 C34 1.1(7) . . . . ?
C32 C31 C36 O3 -174.2(3) . . . . ?
C32 C31 C36 C35 6.1(5) . . . . ?
C32 C33 C34 C35 1.1(7) . . . . ?
C33 C34 C35 C36 0.5(7) . . . . ?
C34 C35 C36 O3 176.1(4) . . . . ?
C34 C35 C36 C31 -4.2(6) . . . . ?
C36 C31 C32 F2 173.9(3) . . . . ?
C36 C31 C32 C33 -4.7(6) . . . . ?
C37 C30 C31 C32 94.6(4) . . . . ?
C37 C30 C31 C36 -83.7(4) . . . . ?
C37 C30 C43 O4 175.8(4) . . . . ?
C37 C30 C43 N6 -2.2(4) . . . . ?
C37 C38 C39 C40 1.8(7) . . . . ?
C38 C37 C42 N6 -179.5(4) . . . . ?
C38 C37 C42 C41 0.9(6) . . . . ?
C38 C39 C40 C41 0.0(8) . . . . ?
C39 C40 C41 C42 -1.4(8) . . . . ?
C40 C41 C42 N6 -178.6(5) . . . . ?
C40 C41 C42 C37 0.9(7) . . . . ?
C42 N6 C43 O4 -176.3(5) . . . . ?
C42 N6 C43 C30 1.8(5) . . . . ?
C42 C37 C38 C39 -2.3(6) . . . . ?
C43 N6 C42 C37 -0.6(5) . . . . ?
C43 N6 C42 C41 179.0(5) . . . . ?
C43 C30 C31 C32 -20.3(5) . . . . ?
C43 C30 C31 C36 161.4(3) . . . . ?
C43 C30 C37 C38 -179.9(4) . . . . ?
C43 C30 C37 C42 1.9(4) . . . . ?
C44 N6 C42 C37 178.9(5) . . . . ?
C44 N6 C42 C41 -1.5(9) . . . . ?
C44 N6 C43 O4 4.2(8) . . . . ?
C44 N6 C43 C30 -177.7(5) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 56 electrons were 
found in a volume of 128Å³ in 1 void per unit cell. 
This is consistent with the presence of 
1.4[H2O] per Asymmetric Unit 
which account for 56 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.027 0.443 0.200 16.1 7.2 '0.7 H2O'
2 -0.027 0.557 0.700 16.1 7.2 '0.7 H2O'
3 0.226 0.575 0.310 16.1 6.0 '0.7 H2O'
4 0.274 0.075 0.810 16.1 6.0 '0.7 H2O'
5 0.473 -0.057 0.700 16.1 7.2 '0.7 H2O'
6 0.527 0.057 0.200 16.1 7.2 '0.7 H2O'
7 0.726 -0.075 0.310 16.1 6.0 '0.7 H2O'
8 0.774 0.425 0.810 16.1 6.0 '0.7 H2O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_platon_squeeze_void_probe_radius 1.20
_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 2.225
_oxdiff_exptl_absorpt_empirical_full_min 0.429
####################################################################### 
# 
# 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_3ae
_database_code_depnum_ccdc_archive 'CCDC 2250263'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-09-16
_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         'C22 H16 Cl N3 O2'
_chemical_formula_sum            'C22 H16 Cl N3 O2'
_chemical_formula_weight         389.83
_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 0.0181 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'
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      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                   10.0502(4)
_cell_length_b                   11.7456(4)
_cell_length_c                   13.2442(5)
_cell_angle_alpha                109.804(4)
_cell_angle_beta                 100.969(3)
_cell_angle_gamma                104.033(3)
_cell_volume                     1362.01(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5537
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3100
_cell_measurement_theta_min      4.2170
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.790
_exptl_absorpt_coefficient_mu    1.374
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.42a (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    0.951
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_recrystallization_method 
'The crystals were growth by means of slow evaporation of DMSO at RT.'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10914
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.450
_diffrn_reflns_theta_min         3.717
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    1.00    --  -35.62  84.00   7.00   99
  2  ω    -16.00  66.00   1.00    1.00    --   35.62 -84.00-112.00   82
  3  ω     39.00 138.00   1.00    1.33    --  107.12 -84.00-112.00   99
  4  ω     98.00 175.00   1.00    1.33    --  107.12  84.00   7.00   77
  5  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00   0.00   73
  6  ω   -107.00  -6.00   1.00    1.00    --  -35.62 -19.00-120.00  101
  7  ω     17.00 105.00   1.00    1.00    --   35.62  38.00-120.00   88
  8  ω      9.00 103.00   1.00    1.00    --   35.62  77.00 120.00   94
  9  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00 150.00   74
 10  ω     60.00 103.00   1.00    1.00    --   35.62 178.00-180.00   43
 11  ω     33.00  61.00   1.00    1.00    --   35.62 -77.00   0.00   28
 12  ω    -31.00  -4.00   1.00    1.00    --   35.62 -77.00   0.00   27
 13  ω     89.00 152.00   1.00    1.33    --  107.12  61.00 -90.00   63
 14  ω    146.00 172.00   1.00    1.33    --  107.12  30.00  30.00   26
 15  ω     53.00 125.00   1.00    1.33    --  107.12 -61.00-150.00   72
 16  ω     38.00  78.00   1.00    1.33    --  107.12 -95.00 150.00   40
 17  ω     39.00 113.00   1.00    1.33    --  107.12-111.00-150.00   74
 18  ω     63.00  89.00   1.00    1.33    --  107.12 178.00  90.00   26
 19  ω     86.00 133.00   1.00    1.33    --  107.12  30.00  30.00   47
 20  ω     82.00 129.00   1.00    1.33    --  107.12 -30.00 -90.00   47
 21  ω     83.00 108.00   1.00    1.33    --  107.12 -95.00 -30.00   25
 22  ω     75.00 123.00   1.00    1.33    --  107.12 -30.00   0.00   48
 23  ω     38.00 123.00   1.00    1.33    --  107.12 -30.00 120.00   85
 24  ω     40.00  65.00   1.00    1.33    --  107.12 -30.00   0.00   25
 25  ω     39.00 110.00   1.00    1.33    --  107.12 -95.00  60.00   71
 26  ω     43.00  73.00   1.00    1.33    --  107.12 -30.00 -90.00   30
 27  ω    102.00 167.00   1.00    1.33    --  107.12 111.00-150.00   65
 28  ω     40.00  69.00   1.00    1.33    --  107.12 -95.00-120.00   29
 29  ω     85.00 110.00   1.00    1.33    --  107.12 -95.00-120.00   25
 30  ω    103.00 176.00   1.00    1.33    --  107.12  45.00 -60.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4246
_reflns_number_total             5158
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_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         0.827
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0079(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         5158
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0822
_refine_ls_restrained_S_all      1.074
_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)+(0.0959P)²+1.9621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2267
_refine_ls_wR_factor_ref         0.2348
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
3. Rigid body (RIGU) restrains
 C14, C13, C12, C11, C10, C9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19)
4.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
4.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.97169(13) 0.08527(15) 0.38181(11) 0.0907(5) Uani 1 1 d . . . . .
O1 O 0.4987(3) 0.3246(3) 0.7191(2) 0.0589(7) Uani 1 1 d . . . . .
O2 O 0.6831(4) 0.4617(3) 0.6002(3) 0.0951(12) Uani 1 1 d . U . . .
H2 H 0.706508 0.490898 0.555628 0.143 Uiso 1 1 calc R U . . .
N1 N 0.6616(3) 0.2096(3) 0.8352(2) 0.0419(6) Uani 1 1 d . . . . .
H1 H 0.603340 0.251236 0.850613 0.050 Uiso 1 1 calc R U . . .
N2 N 0.8196(3) 0.1401(3) 0.7547(2) 0.0446(6) Uani 1 1 d . . . . .
N3 N 0.4939(3) 0.1914(3) 0.5443(2) 0.0444(6) Uani 1 1 d . . . . .
C1 C 0.6983(3) 0.1292(3) 0.8830(3) 0.0421(7) Uani 1 1 d . . . . .
C2 C 0.6519(4) 0.0882(4) 0.9604(3) 0.0541(9) Uani 1 1 d . . . . .
H2A H 0.585649 0.116734 0.993291 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7104(4) 0.0011(4) 0.9865(4) 0.0623(10) Uani 1 1 d . . . . .
H3 H 0.682540 -0.029319 1.038147 0.075 Uiso 1 1 calc R U . . .
C4 C 0.8091(5) -0.0405(4) 0.9365(4) 0.0636(11) Uani 1 1 d . . . . .
H4 H 0.845039 -0.099075 0.954980 0.076 Uiso 1 1 calc R U . . .
C5 C 0.8550(4) 0.0022(4) 0.8610(3) 0.0570(10) Uani 1 1 d . . . . .
H5 H 0.922624 -0.025458 0.829429 0.068 Uiso 1 1 calc R U . . .
C6 C 0.7980(3) 0.0883(3) 0.8323(3) 0.0425(7) Uani 1 1 d . . . . .
C7 C 0.7348(3) 0.2103(3) 0.7593(3) 0.0396(7) Uani 1 1 d . . . . .
C8 C 0.7174(3) 0.2826(3) 0.6846(3) 0.0395(7) Uani 1 1 d . . . . .
C9 C 0.8200(4) 0.4218(3) 0.7417(3) 0.0438(7) Uani 1 1 d . . . . .
C10 C 0.7966(5) 0.5080(4) 0.6946(4) 0.0703(12) Uani 1 1 d . . . . .
C11 C 0.8838(6) 0.6343(4) 0.7454(5) 0.096(2) Uani 1 1 d . . . . .
H11 H 0.865631 0.691970 0.715378 0.116 Uiso 1 1 calc R U . . .
C12 C 0.9985(5) 0.6764(4) 0.8409(4) 0.0807(14) Uani 1 1 d . . . . .
H12 H 1.057432 0.761882 0.874923 0.097 Uiso 1 1 calc R U . . .
C13 C 1.0242(5) 0.5909(4) 0.8849(4) 0.0655(10) Uani 1 1 d . . . . .
H13 H 1.101858 0.618103 0.948313 0.079 Uiso 1 1 calc R U . . .
C14 C 0.9359(4) 0.4657(3) 0.8357(3) 0.0486(8) Uani 1 1 d . . . . .
H14 H 0.954630 0.408864 0.866581 0.058 Uiso 1 1 calc R U . . .
C15 C 0.5951(3) 0.1557(3) 0.4922(3) 0.0407(7) Uani 1 1 d . . . . .
C16 C 0.5720(4) 0.0807(3) 0.3812(3) 0.0510(9) Uani 1 1 d . . . . .
H16 H 0.480538 0.045677 0.329945 0.061 Uiso 1 1 calc R U . . .
C17 C 0.6900(4) 0.0585(4) 0.3476(3) 0.0560(9) Uani 1 1 d . . . . .
H17 H 0.677826 0.006970 0.273300 0.067 Uiso 1 1 calc R U . . .
C18 C 0.8250(4) 0.1133(4) 0.4251(3) 0.0548(9) Uani 1 1 d . . . . .
C19 C 0.8472(4) 0.1873(3) 0.5374(3) 0.0462(8) Uani 1 1 d . . . . .
H19 H 0.938392 0.221596 0.588993 0.055 Uiso 1 1 calc R U . . .
C20 C 0.7308(3) 0.2086(3) 0.5702(3) 0.0399(7) Uani 1 1 d . . . . .
C21 C 0.5577(4) 0.2739(3) 0.6542(3) 0.0447(8) Uani 1 1 d . . . . .
C22 C 0.3432(4) 0.1588(4) 0.4868(4) 0.0602(10) Uani 1 1 d . . . . .
H22A H 0.334587 0.194816 0.431689 0.090 Uiso 1 1 calc R U . . .
H22B H 0.295621 0.192860 0.540353 0.090 Uiso 1 1 calc R U . . .
H22C H 0.299713 0.067224 0.450282 0.090 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 C18 1.743(4) . ?
O1 C21 1.209(4) . ?
O2 H2 0.8200 . ?
O2 C10 1.362(5) . ?
N1 H1 0.8600 . ?
N1 C1 1.384(4) . ?
N1 C7 1.354(4) . ?
N2 C6 1.385(4) . ?
N2 C7 1.317(4) . ?
N3 C15 1.402(4) . ?
N3 C21 1.363(4) . ?
N3 C22 1.449(4) . ?
C1 C2 1.381(5) . ?
C1 C6 1.399(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.402(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.398(5) . ?
C7 C8 1.520(5) . ?
C8 C9 1.535(4) . ?
C8 C20 1.521(4) . ?
C8 C21 1.548(4) . ?
C9 C10 1.399(5) . ?
C9 C14 1.377(5) . ?
C10 C11 1.375(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(5) . ?
C15 C20 1.390(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(5) . ?
C18 C19 1.385(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 O2 H2 109.5 . . ?
C1 N1 H1 126.6 . . ?
C7 N1 H1 126.6 . . ?
C7 N1 C1 106.9(3) . . ?
C7 N2 C6 104.0(3) . . ?
C15 N3 C22 124.9(3) . . ?
C21 N3 C15 111.4(3) . . ?
C21 N3 C22 123.3(3) . . ?
N1 C1 C6 104.5(3) . . ?
C2 C1 N1 132.2(3) . . ?
C2 C1 C6 123.3(3) . . ?
C1 C2 H2A 121.9 . . ?
C1 C2 C3 116.1(4) . . ?
C3 C2 H2A 121.9 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 121.9(4) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.5(4) . . ?
C6 C5 H5 120.8 . . ?
N2 C6 C1 110.8(3) . . ?
N2 C6 C5 130.1(3) . . ?
C5 C6 C1 119.0(3) . . ?
N1 C7 C8 122.8(3) . . ?
N2 C7 N1 113.8(3) . . ?
N2 C7 C8 123.3(3) . . ?
C7 C8 C9 111.9(3) . . ?
C7 C8 C20 110.0(3) . . ?
C7 C8 C21 106.9(3) . . ?
C9 C8 C21 112.4(3) . . ?
C20 C8 C9 113.3(3) . . ?
C20 C8 C21 101.7(3) . . ?
C10 C9 C8 118.5(3) . . ?
C14 C9 C8 123.3(3) . . ?
C14 C9 C10 118.2(3) . . ?
O2 C10 C9 117.1(3) . . ?
O2 C10 C11 122.9(4) . . ?
C11 C10 C9 120.0(4) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(5) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(4) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.6(4) . . ?
C13 C14 H14 119.2 . . ?
C16 C15 N3 127.9(3) . . ?
C16 C15 C20 122.0(3) . . ?
C20 C15 N3 110.1(3) . . ?
C15 C16 H16 121.0 . . ?
C15 C16 C17 117.9(3) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 Cl1 119.3(3) . . ?
C17 C18 C19 122.0(3) . . ?
C19 C18 Cl1 118.7(3) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 C18 118.0(3) . . ?
C20 C19 H19 121.0 . . ?
C15 C20 C8 108.3(3) . . ?
C19 C20 C8 131.4(3) . . ?
C19 C20 C15 120.2(3) . . ?
O1 C21 N3 126.4(3) . . ?
O1 C21 C8 125.6(3) . . ?
N3 C21 C8 107.8(3) . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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 C18 C19 C20 180.0(3) . . . . ?
O2 C10 C11 C12 -179.6(6) . . . . ?
N1 C1 C2 C3 177.6(4) . . . . ?
N1 C1 C6 N2 -1.0(4) . . . . ?
N1 C1 C6 C5 -178.7(3) . . . . ?
N1 C7 C8 C9 88.0(4) . . . . ?
N1 C7 C8 C20 -145.1(3) . . . . ?
N1 C7 C8 C21 -35.4(4) . . . . ?
N2 C7 C8 C9 -93.6(4) . . . . ?
N2 C7 C8 C20 33.3(4) . . . . ?
N2 C7 C8 C21 142.9(3) . . . . ?
N3 C15 C16 C17 179.5(3) . . . . ?
N3 C15 C20 C8 1.7(4) . . . . ?
N3 C15 C20 C19 -179.3(3) . . . . ?
C1 N1 C7 N2 -1.7(4) . . . . ?
C1 N1 C7 C8 176.8(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C1 C6 N2 177.3(3) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C3 C4 C5 C6 -1.3(6) . . . . ?
C4 C5 C6 N2 -176.1(4) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C6 N2 C7 N1 1.0(4) . . . . ?
C6 N2 C7 C8 -177.5(3) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C7 N1 C1 C2 -176.5(4) . . . . ?
C7 N1 C1 C6 1.5(3) . . . . ?
C7 N2 C6 C1 0.1(4) . . . . ?
C7 N2 C6 C5 177.4(4) . . . . ?
C7 C8 C9 C10 -166.7(4) . . . . ?
C7 C8 C9 C14 14.7(5) . . . . ?
C7 C8 C20 C15 107.3(3) . . . . ?
C7 C8 C20 C19 -71.5(4) . . . . ?
C7 C8 C21 O1 68.0(4) . . . . ?
C7 C8 C21 N3 -107.3(3) . . . . ?
C8 C9 C10 O2 -0.1(7) . . . . ?
C8 C9 C10 C11 178.1(5) . . . . ?
C8 C9 C14 C13 -179.3(4) . . . . ?
C9 C8 C20 C15 -126.7(3) . . . . ?
C9 C8 C20 C19 54.5(5) . . . . ?
C9 C8 C21 O1 -55.1(5) . . . . ?
C9 C8 C21 N3 129.5(3) . . . . ?
C9 C10 C11 C12 2.4(10) . . . . ?
C10 C9 C14 C13 2.0(6) . . . . ?
C10 C11 C12 C13 -0.2(10) . . . . ?
C11 C12 C13 C14 -1.0(8) . . . . ?
C12 C13 C14 C9 0.1(7) . . . . ?
C14 C9 C10 O2 178.6(4) . . . . ?
C14 C9 C10 C11 -3.3(7) . . . . ?
C15 N3 C21 O1 177.0(3) . . . . ?
C15 N3 C21 C8 -7.6(4) . . . . ?
C15 C16 C17 C18 -1.0(6) . . . . ?
C16 C15 C20 C8 -178.5(3) . . . . ?
C16 C15 C20 C19 0.5(5) . . . . ?
C16 C17 C18 Cl1 -179.7(3) . . . . ?
C16 C17 C18 C19 2.1(6) . . . . ?
C17 C18 C19 C20 -1.8(6) . . . . ?
C18 C19 C20 C8 179.3(3) . . . . ?
C18 C19 C20 C15 0.6(5) . . . . ?
C20 C8 C9 C10 68.3(4) . . . . ?
C20 C8 C9 C14 -110.4(4) . . . . ?
C20 C8 C21 O1 -176.6(3) . . . . ?
C20 C8 C21 N3 8.0(3) . . . . ?
C20 C15 C16 C17 -0.2(5) . . . . ?
C21 N3 C15 C16 -175.8(3) . . . . ?
C21 N3 C15 C20 3.9(4) . . . . ?
C21 C8 C9 C10 -46.4(5) . . . . ?
C21 C8 C9 C14 135.0(3) . . . . ?
C21 C8 C20 C15 -5.8(3) . . . . ?
C21 C8 C20 C19 175.4(4) . . . . ?
C22 N3 C15 C16 -3.1(6) . . . . ?
C22 N3 C15 C20 176.7(3) . . . . ?
C22 N3 C21 O1 4.1(6) . . . . ?
C22 N3 C21 C8 179.5(3) . . . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.004 0.500 0.496 526 170 '3 CHCl3'

_platon_squeeze_void_probe_radius 1.20
_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
;
