# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_047-648_auto
_database_code_depnum_ccdc_archive 'CCDC 2488000'
loop_
_audit_author_name
_audit_author_address
'Roman Kuznetsov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2025-09-14 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2025-09-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.571(C18 H14 Cl N3 O2)'
_chemical_formula_sum            'C10.29 H8 Cl0.57 N1.71 O1.14'
_chemical_formula_weight         194.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H14ClN3O3
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.05750(10)
_cell_length_b                   9.68530(10)
_cell_length_c                   9.10770(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.0140(10)
_cell_angle_gamma                90
_cell_volume                     1545.46(3)
_cell_formula_units_Z            7
_cell_measurement_reflns_used    20622
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.2920
_cell_measurement_theta_min      2.5600
_shelx_estimated_absorpt_T_max   0.836
_shelx_estimated_absorpt_T_min   0.736
_exptl_absorpt_coefficient_mu    2.328
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light white'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            30604
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.923
_diffrn_reflns_theta_min         2.522
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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    -26.00  28.00   0.50    0.05    --  -47.34  19.00  30.00  108
  2  ω    -42.00  26.00   0.50    0.05    --  -47.34  37.00  90.00  136
  3  ω    -70.00  25.00   0.50    0.05    --  -47.34  77.00 -30.00  190
  4  ω    -70.00  25.00   0.50    0.05    --  -47.34  77.00 -30.00  190
  5  ω    -26.00  28.00   0.50    0.05    --  -47.34  19.00-120.00  108
  6  ω   -106.00 -33.00   0.50    0.20    -- -106.00  77.00 -60.00  146
  7  ω    -71.00 -33.00   0.50    0.20    -- -106.00  61.00-120.00   76
  8  ω   -106.00 -33.00   0.50    0.20    -- -106.00  77.00 -90.00  146
  9  ω   -125.00 -33.00   0.50    0.20    -- -106.00 143.00 -52.05  184
 10  ω   -125.00 -33.00   0.50    0.20    -- -106.00 143.00 -52.05  184
 11  ω   -112.00 -36.00   0.50    0.20    -- -106.00 125.00  60.00  152
 12  ω   -122.00 -33.00   0.50    0.20    -- -106.00 139.00  56.22  178
 13  ω   -127.00 -33.00   0.50    0.20    -- -106.00 146.00 113.24  188
 14  ω   -127.00 -33.00   0.50    0.20    -- -106.00 146.00 113.24  188
 15  ω   -118.00 -35.00   0.50    0.20    -- -106.00 134.00  89.33  166
 16  ω   -112.00 -36.00   0.50    0.20    -- -106.00 125.00  60.00  152
 17  ω   -112.00 -36.00   0.50    0.20    -- -106.00 125.00 -90.00  152
 18  ω   -108.00 -36.00   0.50    0.20    -- -106.00 110.00 -82.47  144
 19  ω   -108.00 -36.00   0.50    0.20    -- -106.00 110.00 -82.47  144
 20  ω   -108.00 -37.00   0.50    0.20    -- -106.00 111.00 -42.29  142
 21  ω   -177.00 -92.00   0.50    0.20    -- -106.00 -15.00 150.00  170
 22  ω   -177.00 -92.00   0.50    0.20    -- -106.00 -51.00  73.37  170
 23  ω   -177.00 -86.00   0.50    0.20    -- -106.00 -69.00-134.59  182
 24  ω   -177.00 -87.00   0.50    0.20    -- -106.00 -68.00-169.58  180
 25  ω   -177.00 -87.00   0.50    0.20    -- -106.00 -68.00-169.58  180
 26  ω   -177.00 -92.00   0.50    0.20    -- -106.00 -51.00-107.28  170
 27  ω   -177.00 -92.00   0.50    0.20    -- -106.00 -48.00 -36.58  170
 28  ω   -177.00 -93.00   0.50    0.20    -- -106.00 -47.00 146.20  168
 29  ω   -122.00 -35.00   0.50    0.05    --  -47.34 -19.00  60.00  174
 30  ω     54.00  96.00   0.50    0.20    --  113.25 -77.00  30.00   84
 31  ω     44.00  70.00   0.50    0.20    --  113.25 -61.00  60.00   52
 32  ω     43.00  69.00   0.50    0.20    --  113.25 -61.00   0.00   52
 33  ω     42.00  67.00   0.50    0.20    --  113.25 -61.00-150.00   50
 34  ω     44.00  71.00   0.50    0.20    --  113.25 -61.00-180.00   54
 35  ω     13.00  93.00   0.50    0.05    --   47.34-125.00 -60.00  160
 36  ω     13.00  93.00   0.50    0.05    --   47.34-125.00-120.00  160
 37  ω     71.00 102.00   0.50    0.20    --  113.25-125.00 -90.00   62
 38  ω     52.00 103.00   0.50    0.20    --  113.25 -94.00-180.00  102
 39  ω     80.00 109.00   0.50    0.20    --  113.25-125.00  30.00   58
 40  ω     48.00  95.00   0.50    0.20    --  113.25-108.00  36.68   94
 41  ω     43.00  69.00   0.50    0.20    --  113.25 -94.00  60.00   52
 42  ω     43.00 102.00   0.50    0.20    --  113.25 -94.00 150.00  118
 43  ω    112.00 158.00   0.50    0.20    --  113.25  15.00  60.00   92
 44  ω     97.00 164.00   0.50    0.20    --  113.25  61.00  60.00  134
 45  ω    -27.00  26.00   0.50    0.05    --   47.34 -19.00-120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0855528000
_diffrn_orient_matrix_UB_12      -0.0086621000
_diffrn_orient_matrix_UB_13      -0.0030099000
_diffrn_orient_matrix_UB_21      0.0015562000
_diffrn_orient_matrix_UB_22      -0.1568745000
_diffrn_orient_matrix_UB_23      -0.0268692000
_diffrn_orient_matrix_UB_31      0.0203114000
_diffrn_orient_matrix_UB_32      -0.0246596000
_diffrn_orient_matrix_UB_33      0.1722314000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3097
_reflns_number_total             3270
_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 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.076
_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)+(0.0572P)²+0.6855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.0995
_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:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C17(H17a,H17b)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C8(H8), C13(H13), C14(H14), C11(H11), C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.43353(2) 0.24754(3) -0.03941(4) 0.02482(12) Uani 1 1 d . . . . .
O2 O 0.95770(5) 0.08783(10) 0.77292(11) 0.0208(2) Uani 1 1 d . . . . .
O1 O 0.94606(6) 0.29030(11) 0.65133(11) 0.0235(2) Uani 1 1 d . . . . .
N3 N 0.70990(6) 0.45717(11) 0.57080(12) 0.0164(2) Uani 1 1 d . . . . .
N1 N 0.78958(6) 0.29492(11) 0.67836(12) 0.0160(2) Uani 1 1 d . . . . .
N2 N 0.74431(6) 0.23378(11) 0.55369(12) 0.0170(2) Uani 1 1 d . . . . .
C1 C 0.69692(7) 0.33507(13) 0.49418(14) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.76834(7) 0.42897(13) 0.68609(14) 0.0158(2) Uani 1 1 d . . . . .
C3 C 0.80182(7) 0.52908(13) 0.80576(14) 0.0167(3) Uani 1 1 d . . . . .
C9 C 0.63418(7) 0.31473(13) 0.35913(14) 0.0167(3) Uani 1 1 d . . . . .
C15 C 0.84818(7) 0.21447(13) 0.77958(14) 0.0164(3) Uani 1 1 d . . . . .
H15 H 0.8609 0.2624 0.8918 0.020 Uiso 1 1 calc R U . . .
C10 C 0.58960(8) 0.42647(14) 0.29307(15) 0.0195(3) Uani 1 1 d . . . . .
H10 H 0.6031 0.5297 0.3379 0.023 Uiso 1 1 calc R U . . .
C16 C 0.83043(7) 0.06184(13) 0.79577(15) 0.0192(3) Uani 1 1 d . . . . .
H16A H 0.7968 0.0459 0.8795 0.023 Uiso 1 1 calc R U . . .
H16B H 0.8003 0.0168 0.6875 0.023 Uiso 1 1 calc R U . . .
C4 C 0.75244(8) 0.62222(14) 0.85169(15) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.6917 0.6185 0.7998 0.024 Uiso 1 1 calc R U . . .
C8 C 0.88028(8) 0.53761(14) 0.86951(14) 0.0189(3) Uani 1 1 d . . . . .
H8 H 0.9192 0.4680 0.8324 0.023 Uiso 1 1 calc R U . . .
C13 C 0.55688(7) 0.16185(14) 0.17338(15) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.5449 0.0598 0.1243 0.023 Uiso 1 1 calc R U . . .
C14 C 0.61719(7) 0.18268(14) 0.29903(15) 0.0183(3) Uani 1 1 d . . . . .
H14 H 0.6514 0.0954 0.3509 0.022 Uiso 1 1 calc R U . . .
C12 C 0.51240(8) 0.27397(15) 0.11208(15) 0.0190(3) Uani 1 1 d . . . . .
C11 C 0.52783(8) 0.40597(14) 0.16994(15) 0.0205(3) Uani 1 1 d . . . . .
H11 H 0.4922 0.4922 0.1199 0.025 Uiso 1 1 calc R U . . .
C18 C 0.92180(7) 0.20635(14) 0.72513(14) 0.0175(3) Uani 1 1 d . . . . .
C5 C 0.78099(9) 0.71948(15) 0.96357(16) 0.0235(3) Uani 1 1 d . . . . .
H5 H 0.7425 0.7905 0.9999 0.028 Uiso 1 1 calc R U . . .
C6 C 0.85900(9) 0.72547(15) 1.02876(16) 0.0237(3) Uani 1 1 d . . . . .
H6 H 0.8813 0.8003 1.1171 0.028 Uiso 1 1 calc R U . . .
C17 C 0.91073(7) 0.00337(14) 0.84961(15) 0.0199(3) Uani 1 1 d . . . . .
H17A H 0.9309 0.0123 0.9727 0.024 Uiso 1 1 calc R U . . .
H17B H 0.9122 -0.1054 0.8178 0.024 Uiso 1 1 calc R U . . .
C7 C 0.90842(8) 0.63573(14) 0.98085(15) 0.0220(3) Uani 1 1 d . . . . .
H7 H 0.9693 0.6421 1.0305 0.026 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 C12 1.7452(14) . ?
O2 C18 1.3382(16) . ?
O2 C17 1.4708(15) . ?
O1 C18 1.2030(18) . ?
N3 C1 1.3643(17) . ?
N3 C2 1.3244(17) . ?
N1 N2 1.3633(15) . ?
N1 C2 1.3604(17) . ?
N1 C15 1.4506(16) . ?
N2 C1 1.3282(17) . ?
C1 C9 1.4698(17) . ?
C2 C3 1.4746(18) . ?
C3 C4 1.4016(18) . ?
C3 C8 1.3974(18) . ?
C9 C10 1.3953(18) . ?
C9 C14 1.3957(18) . ?
C15 H15 1.0950 . ?
C15 C16 1.5274(18) . ?
C15 C18 1.5292(18) . ?
C10 H10 1.0850 . ?
C10 C11 1.3911(18) . ?
C16 H16A 1.0950 . ?
C16 H16B 1.0950 . ?
C16 C17 1.5230(17) . ?
C4 H4 1.0850 . ?
C4 C5 1.3918(19) . ?
C8 H8 1.0850 . ?
C8 C7 1.3928(19) . ?
C13 H13 1.0850 . ?
C13 C14 1.3903(18) . ?
C13 C12 1.385(2) . ?
C14 H14 1.0850 . ?
C12 C11 1.385(2) . ?
C11 H11 1.0850 . ?
C5 H5 1.0850 . ?
C5 C6 1.391(2) . ?
C6 H6 1.0850 . ?
C6 C7 1.390(2) . ?
C17 H17A 1.0950 . ?
C17 H17B 1.0950 . ?
C7 H7 1.0850 . ?

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
C18 O2 C17 109.99(10) . . ?
C2 N3 C1 103.41(10) . . ?
N2 N1 C15 119.60(10) . . ?
C2 N1 N2 109.75(10) . . ?
C2 N1 C15 130.63(11) . . ?
C1 N2 N1 102.48(10) . . ?
N3 C1 C9 123.12(11) . . ?
N2 C1 N3 114.69(11) . . ?
N2 C1 C9 122.17(12) . . ?
N3 C2 N1 109.66(11) . . ?
N3 C2 C3 123.76(11) . . ?
N1 C2 C3 126.54(12) . . ?
C4 C3 C2 117.85(12) . . ?
C8 C3 C2 122.61(12) . . ?
C8 C3 C4 119.49(12) . . ?
C10 C9 C1 120.28(12) . . ?
C10 C9 C14 119.51(12) . . ?
C14 C9 C1 120.18(12) . . ?
N1 C15 H15 108.8 . . ?
N1 C15 C16 116.32(11) . . ?
N1 C15 C18 112.29(10) . . ?
C16 C15 H15 108.8 . . ?
C16 C15 C18 101.59(10) . . ?
C18 C15 H15 108.8 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.21(12) . . ?
C11 C10 H10 119.9 . . ?
C15 C16 H16A 111.6 . . ?
C15 C16 H16B 111.6 . . ?
H16A C16 H16B 109.4 . . ?
C17 C16 C15 100.67(10) . . ?
C17 C16 H16A 111.6 . . ?
C17 C16 H16B 111.6 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.30(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C8 H8 120.1 . . ?
C7 C8 C3 119.82(12) . . ?
C7 C8 H8 120.1 . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.70(13) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.65(12) . . ?
C13 C14 H14 119.7 . . ?
C13 C12 Cl1 119.09(11) . . ?
C11 C12 Cl1 119.12(11) . . ?
C11 C12 C13 121.77(12) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.12(13) . . ?
C12 C11 H11 120.4 . . ?
O2 C18 C15 109.23(11) . . ?
O1 C18 O2 123.24(12) . . ?
O1 C18 C15 127.53(12) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.87(13) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.06(13) . . ?
C7 C6 H6 120.0 . . ?
O2 C17 C16 104.71(10) . . ?
O2 C17 H17A 110.8 . . ?
O2 C17 H17B 110.8 . . ?
C16 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
C8 C7 H7 119.8 . . ?
C6 C7 C8 120.44(13) . . ?
C6 C7 H7 119.8 . . ?

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 C12 C11 C10 178.44(10) . . . . ?
N3 C1 C9 C10 7.21(19) . . . . ?
N3 C1 C9 C14 -170.68(12) . . . . ?
N3 C2 C3 C4 35.54(18) . . . . ?
N3 C2 C3 C8 -141.85(13) . . . . ?
N1 N2 C1 N3 1.22(14) . . . . ?
N1 N2 C1 C9 -176.96(11) . . . . ?
N1 C2 C3 C4 -141.93(13) . . . . ?
N1 C2 C3 C8 40.68(19) . . . . ?
N1 C15 C16 C17 157.43(10) . . . . ?
N1 C15 C18 O2 -150.98(11) . . . . ?
N1 C15 C18 O1 29.17(19) . . . . ?
N2 N1 C2 N3 0.62(14) . . . . ?
N2 N1 C2 C3 178.38(11) . . . . ?
N2 N1 C15 C16 -32.60(16) . . . . ?
N2 N1 C15 C18 83.81(14) . . . . ?
N2 C1 C9 C10 -174.76(12) . . . . ?
N2 C1 C9 C14 7.36(19) . . . . ?
C1 N3 C2 N1 0.13(13) . . . . ?
C1 N3 C2 C3 -177.71(11) . . . . ?
C1 C9 C10 C11 -176.72(12) . . . . ?
C1 C9 C14 C13 178.53(12) . . . . ?
C2 N3 C1 N2 -0.88(14) . . . . ?
C2 N3 C1 C9 177.29(11) . . . . ?
C2 N1 N2 C1 -1.08(13) . . . . ?
C2 N1 C15 C16 145.64(13) . . . . ?
C2 N1 C15 C18 -97.94(15) . . . . ?
C2 C3 C4 C5 -179.63(12) . . . . ?
C2 C3 C8 C7 179.16(12) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C3 C8 C7 C6 -0.2(2) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
C15 N1 N2 C1 177.51(11) . . . . ?
C15 N1 C2 N3 -177.76(12) . . . . ?
C15 N1 C2 C3 0.0(2) . . . . ?
C15 C16 C17 O2 -33.80(12) . . . . ?
C10 C9 C14 C13 0.63(19) . . . . ?
C16 C15 C18 O2 -26.00(13) . . . . ?
C16 C15 C18 O1 154.14(13) . . . . ?
C4 C3 C8 C7 1.81(19) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C8 C3 C4 C5 -2.15(19) . . . . ?
C13 C12 C11 C10 -0.1(2) . . . . ?
C14 C9 C10 C11 1.17(19) . . . . ?
C14 C13 C12 Cl1 -176.67(10) . . . . ?
C14 C13 C12 C11 1.9(2) . . . . ?
C12 C13 C14 C9 -2.12(19) . . . . ?
C18 O2 C17 C16 19.09(13) . . . . ?
C18 C15 C16 C17 35.20(12) . . . . ?
C5 C6 C7 C8 -1.2(2) . . . . ?
C17 O2 C18 O1 -175.59(12) . . . . ?
C17 O2 C18 C15 4.54(13) . . . . ?

_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 1.751
_oxdiff_exptl_absorpt_empirical_full_min 0.783
####################################################################### 
# 
# 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_044-265_auto
_database_code_depnum_ccdc_archive 'CCDC 2488001'
loop_
_audit_author_name
_audit_author_address
'Roman Kuznetsov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2025-09-14 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2025-09-12
_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         'C23 H15 Cl F3 N3 O'
_chemical_formula_sum            'C23 H15 Cl F3 N3 O'
_chemical_formula_weight         441.83
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.1094(9)
_cell_length_b                   4.6693(4)
_cell_length_c                   20.8977(11)
_cell_angle_alpha                90
_cell_angle_beta                 107.207(5)
_cell_angle_gamma                90
_cell_volume                     1967.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.4180
_cell_measurement_theta_min      3.6890
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    2.162
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.85681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_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    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15490
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.230
_diffrn_reflns_theta_min         2.191
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  044-265_auto
_diffrn_measurement_method       ?
_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                2953
_reflns_number_total             3983
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0770
_refine_ls_restrained_S_all      1.122
_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)+(0.0867P)²+1.3702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.1887
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
1.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C20(H20), C2(H2), C11(H11), C17(H17), C16(H16), C3(H3), C14(H14),
 C6(H6), C13(H13), C19(H19), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.56368(4) -0.0459(3) 0.94717(4) 0.0386(3) Uani 1 1 d . . . . .
F2 F 0.29904(11) -0.4527(6) 0.43382(11) 0.0387(6) Uani 1 1 d . . . . .
F3 F 0.20283(11) -0.3737(6) 0.36541(11) 0.0434(7) Uani 1 1 d . . . . .
F1 F 0.28305(14) -0.0848(6) 0.37012(12) 0.0449(7) Uani 1 1 d . . . . .
O1 O 0.34642(11) 0.6685(6) 0.70032(12) 0.0276(6) Uani 1 1 d . . . . .
N3 N 0.13839(13) 0.6466(7) 0.58479(14) 0.0229(7) Uani 1 1 d . . . . .
N1 N 0.21832(12) 0.4875(7) 0.66973(13) 0.0216(7) Uani 1 1 d . . . . .
N2 N 0.18709(12) 0.6869(7) 0.69644(13) 0.0215(6) Uani 1 1 d . . . . .
C7 C 0.13874(14) 0.7757(9) 0.64319(15) 0.0214(8) Uani 1 1 d . . . . .
C15 C 0.39249(14) 0.3301(9) 0.78581(15) 0.0214(8) Uani 1 1 d . . . . .
C8 C 0.18934(15) 0.4664(9) 0.60271(16) 0.0232(8) Uani 1 1 d . . . . .
C1 C 0.08927(15) 0.9907(9) 0.64767(17) 0.0236(8) Uani 1 1 d . . . . .
C10 C 0.15956(15) 0.2097(9) 0.49579(16) 0.0271(9) Uani 1 1 d . . . . .
H10 H 0.115943 0.283589 0.487555 0.033 Uiso 1 1 calc R U . . .
C21 C 0.33754(15) 0.4625(9) 0.73117(15) 0.0210(7) Uani 1 1 d . . . . .
C9 C 0.20797(15) 0.2766(8) 0.55586(16) 0.0211(7) Uani 1 1 d . . . . .
C20 C 0.38177(15) 0.1140(8) 0.82699(16) 0.0232(8) Uani 1 1 d . . . . .
H20 H 0.338111 0.043735 0.820688 0.028 Uiso 1 1 calc R U . . .
C22 C 0.26986(14) 0.3200(9) 0.71583(16) 0.0224(8) Uani 1 1 d . . . . .
H22A H 0.271934 0.128515 0.696222 0.027 Uiso 1 1 calc R U . . .
H22B H 0.258460 0.293157 0.758109 0.027 Uiso 1 1 calc R U . . .
C2 C 0.09164(16) 1.1265(9) 0.70726(17) 0.0270(8) Uani 1 1 d . . . . .
H2 H 0.126727 1.084651 0.746607 0.032 Uiso 1 1 calc R U . . .
C11 C 0.17421(16) 0.0387(9) 0.44852(16) 0.0269(8) Uani 1 1 d . . . . .
H11 H 0.140895 -0.003186 0.407809 0.032 Uiso 1 1 calc R U . . .
C12 C 0.23770(16) -0.0734(9) 0.46016(16) 0.0241(8) Uani 1 1 d . . . . .
C17 C 0.50989(15) 0.3135(10) 0.84482(16) 0.0287(9) Uani 1 1 d . . . . .
H17 H 0.553804 0.379376 0.850588 0.034 Uiso 1 1 calc R U . . .
C16 C 0.45720(15) 0.4283(9) 0.79545(17) 0.0258(8) Uani 1 1 d . . . . .
H16 H 0.465093 0.576406 0.767591 0.031 Uiso 1 1 calc R U . . .
C3 C 0.04320(17) 1.3233(10) 0.71001(18) 0.0297(9) Uani 1 1 d . . . . .
H3 H 0.045174 1.415674 0.751061 0.036 Uiso 1 1 calc R U . . .
C14 C 0.27212(15) 0.1661(9) 0.56657(17) 0.0279(8) Uani 1 1 d . . . . .
H14 H 0.305904 0.212041 0.606644 0.033 Uiso 1 1 calc R U . . .
C00P C 0.25514(17) -0.2459(10) 0.40798(17) 0.0287(8) Uani 1 1 d . . . . .
C6 C 0.03695(16) 1.0521(9) 0.59006(17) 0.0277(8) Uani 1 1 d . . . . .
H6 H 0.034492 0.958498 0.549034 0.033 Uiso 1 1 calc R U . . .
C13 C 0.28662(16) -0.0083(10) 0.51961(17) 0.0299(9) Uani 1 1 d . . . . .
H13 H 0.330032 -0.084310 0.527747 0.036 Uiso 1 1 calc R U . . .
C19 C 0.43420(16) -0.0006(10) 0.87734(17) 0.0285(9) Uani 1 1 d . . . . .
H19 H 0.426713 -0.147306 0.905776 0.034 Uiso 1 1 calc R U . . .
C4 C -0.00817(17) 1.3847(10) 0.65251(19) 0.0306(9) Uani 1 1 d . . . . .
H4 H -0.041308 1.519914 0.654067 0.037 Uiso 1 1 calc R U . . .
C18 C 0.49767(15) 0.1028(9) 0.88536(16) 0.0280(9) Uani 1 1 d . . . . .
C5 C -0.01090(16) 1.2480(10) 0.59292(18) 0.0311(9) Uani 1 1 d . . . . .
H5 H -0.046098 1.289819 0.553665 0.037 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 1.740(3) . ?
F2 C00P 1.337(5) . ?
F3 C00P 1.336(4) . ?
F1 C00P 1.347(5) . ?
O1 C21 1.203(5) . ?
N3 C7 1.359(4) . ?
N3 C8 1.329(5) . ?
N1 N2 1.353(4) . ?
N1 C8 1.356(4) . ?
N1 C22 1.450(4) . ?
N2 C7 1.334(4) . ?
C7 C1 1.472(5) . ?
C15 C21 1.499(4) . ?
C15 C20 1.387(5) . ?
C15 C16 1.398(4) . ?
C8 C9 1.458(5) . ?
C1 C2 1.385(5) . ?
C1 C6 1.402(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.400(4) . ?
C10 C11 1.375(5) . ?
C21 C22 1.521(4) . ?
C9 C14 1.404(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.389(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.388(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(5) . ?
C12 C00P 1.487(5) . ?
C12 C13 1.394(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.382(5) . ?
C17 C18 1.371(6) . ?
C16 H16 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.390(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.377(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.377(6) . ?
C13 H13 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.387(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(6) . ?
C5 H5 0.9500 . ?

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
C8 N3 C7 103.8(3) . . ?
N2 N1 C8 110.5(3) . . ?
N2 N1 C22 117.3(3) . . ?
C8 N1 C22 131.9(3) . . ?
C7 N2 N1 102.4(3) . . ?
N3 C7 C1 123.0(3) . . ?
N2 C7 N3 114.3(3) . . ?
N2 C7 C1 122.7(3) . . ?
C20 C15 C21 122.7(3) . . ?
C20 C15 C16 118.7(3) . . ?
C16 C15 C21 118.5(3) . . ?
N3 C8 N1 109.0(3) . . ?
N3 C8 C9 123.5(3) . . ?
N1 C8 C9 127.5(3) . . ?
C2 C1 C7 122.1(3) . . ?
C2 C1 C6 119.2(3) . . ?
C6 C1 C7 118.6(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C11 C10 C9 121.0(3) . . ?
O1 C21 C15 122.0(3) . . ?
O1 C21 C22 121.5(3) . . ?
C15 C21 C22 116.6(3) . . ?
C10 C9 C8 117.9(3) . . ?
C10 C9 C14 118.4(3) . . ?
C14 C9 C8 123.7(3) . . ?
C15 C20 H20 119.7 . . ?
C15 C20 C19 120.7(3) . . ?
C19 C20 H20 119.7 . . ?
N1 C22 C21 112.2(3) . . ?
N1 C22 H22A 109.2 . . ?
N1 C22 H22B 109.2 . . ?
C21 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C00P 120.7(3) . . ?
C11 C12 C13 119.7(3) . . ?
C13 C12 C00P 119.5(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C18 C17 C16 118.8(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.1(4) . . ?
C17 C16 H16 119.4 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
F2 C00P F1 105.6(3) . . ?
F2 C00P C12 112.8(3) . . ?
F3 C00P F2 106.5(4) . . ?
F3 C00P F1 106.1(3) . . ?
F3 C00P C12 113.3(3) . . ?
F1 C00P C12 112.0(4) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C20 C19 H19 120.6 . . ?
C18 C19 C20 118.8(4) . . ?
C18 C19 H19 120.6 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C17 C18 Cl1 119.3(3) . . ?
C17 C18 C19 121.8(3) . . ?
C19 C18 Cl1 118.9(3) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C21 C22 N1 -9.6(5) . . . . ?
N3 C7 C1 C2 -177.9(3) . . . . ?
N3 C7 C1 C6 4.2(5) . . . . ?
N3 C8 C9 C10 -21.7(5) . . . . ?
N3 C8 C9 C14 155.9(4) . . . . ?
N1 N2 C7 N3 -0.8(4) . . . . ?
N1 N2 C7 C1 178.0(3) . . . . ?
N1 C8 C9 C10 156.8(4) . . . . ?
N1 C8 C9 C14 -25.5(6) . . . . ?
N2 N1 C8 N3 -1.1(4) . . . . ?
N2 N1 C8 C9 -179.8(3) . . . . ?
N2 N1 C22 C21 -88.7(3) . . . . ?
N2 C7 C1 C2 3.3(6) . . . . ?
N2 C7 C1 C6 -174.5(3) . . . . ?
C7 N3 C8 N1 0.5(4) . . . . ?
C7 N3 C8 C9 179.3(3) . . . . ?
C7 C1 C2 C3 -178.4(4) . . . . ?
C7 C1 C6 C5 178.7(4) . . . . ?
C15 C21 C22 N1 171.3(3) . . . . ?
C15 C20 C19 C18 -0.6(6) . . . . ?
C8 N3 C7 N2 0.2(4) . . . . ?
C8 N3 C7 C1 -178.6(3) . . . . ?
C8 N1 N2 C7 1.1(4) . . . . ?
C8 N1 C22 C21 98.8(4) . . . . ?
C8 C9 C14 C13 -178.9(4) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C1 C6 C5 C4 -0.4(6) . . . . ?
C10 C9 C14 C13 -1.2(6) . . . . ?
C10 C11 C12 C00P -176.7(4) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?
C21 C15 C20 C19 -179.5(3) . . . . ?
C21 C15 C16 C17 -179.7(3) . . . . ?
C9 C10 C11 C12 0.6(6) . . . . ?
C9 C14 C13 C12 1.0(6) . . . . ?
C20 C15 C21 O1 172.4(3) . . . . ?
C20 C15 C21 C22 -8.5(5) . . . . ?
C20 C15 C16 C17 0.1(5) . . . . ?
C20 C19 C18 Cl1 -178.6(3) . . . . ?
C20 C19 C18 C17 -0.3(6) . . . . ?
C22 N1 N2 C7 -172.9(3) . . . . ?
C22 N1 C8 N3 171.8(3) . . . . ?
C22 N1 C8 C9 -6.9(6) . . . . ?
C2 C1 C6 C5 0.8(6) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C11 C10 C9 C8 178.2(4) . . . . ?
C11 C10 C9 C14 0.4(6) . . . . ?
C11 C12 C00P F2 -146.5(4) . . . . ?
C11 C12 C00P F3 -25.4(5) . . . . ?
C11 C12 C00P F1 94.5(4) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C16 C15 C21 O1 -7.8(5) . . . . ?
C16 C15 C21 C22 171.3(3) . . . . ?
C16 C15 C20 C19 0.7(5) . . . . ?
C16 C17 C18 Cl1 179.4(3) . . . . ?
C16 C17 C18 C19 1.1(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C00P C12 C13 C14 176.0(4) . . . . ?
C6 C1 C2 C3 -0.6(6) . . . . ?
C13 C12 C00P F2 37.6(5) . . . . ?
C13 C12 C00P F3 158.6(4) . . . . ?
C13 C12 C00P F1 -81.4(4) . . . . ?
C18 C17 C16 C15 -1.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
