# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_anzhenyu_0607_auto
_database_code_depnum_ccdc_archive 'CCDC 2287787'
loop_
_audit_author_name
_audit_author_address
'Zhenyu An'
;Ningxia Medical University
China
;
_audit_update_record             
;
2023-08-09 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;
_audit_creation_date             2021-06-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 F N2 O'
_chemical_formula_sum            'C22 H19 F N2 O'
_chemical_formula_weight         346.39
_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'
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                   7.38752(8)
_cell_length_b                   13.87031(12)
_cell_length_c                   16.86229(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.3714(10)
_cell_angle_gamma                90
_cell_volume                     1687.71(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14676
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      76.7000
_cell_measurement_theta_min      3.1820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
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    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18850
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.478
_diffrn_reflns_theta_min         4.167
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.949
_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  30.00   0.50    0.05    --   47.57 -29.00 -65.00  112
  2  ω     -9.00  22.00   0.50    0.05    --   47.57 -19.00-120.00   62
  3  ω    -24.00  18.00   0.50    0.05    --   47.57 -19.00-150.00   84
  4  ω     37.00  62.00   0.50    0.05    --  107.75 -57.00 -60.00   50
  5  ω     35.00  61.00   0.50    0.05    --  107.75 -57.00 -90.00   52
  6  ω     72.00  97.00   0.50    0.05    --  107.75 -77.00-180.00   50
  7  ω     61.00  94.00   0.50    0.05    --  107.75-125.00-124.00   66
  8  ω   -105.00 -29.00   0.50    0.05    -- -100.00 125.00 -46.00  152
  9  ω    -59.00 -32.00   0.50    0.05    -- -100.00  57.00   0.00   54
 10  ω    -69.00 -43.00   0.50    0.05    -- -100.00  57.00 -90.00   52
 11  ω    -62.00 -28.00   0.50    0.05    -- -100.00  57.00-180.00   68
 12  ω   -136.00-105.00   0.50    0.05    -- -100.00 -29.00 -65.00   62
 13  ω   -118.00 -68.00   0.50    0.05    --  -47.57-145.00  68.00  100
 14  ω   -166.00-100.00   0.50    0.05    -- -100.00 -94.00 126.00  132
 15  ω    -13.00  50.00   0.50    0.05    --   47.57 -94.00 126.00  126
 16  ω    -25.00  17.00   0.50    0.05    --   47.57 -37.00   0.00   84
 17  ω    -27.00  -1.00   0.50    0.05    --   47.57 -19.00  30.00   52
 18  ω   -159.00-100.00   0.50    0.05    -- -100.00 -37.00 150.00  118
 19  ω   -105.00 -79.00   0.50    0.05    -- -100.00  77.00  30.00   52
 20  ω    -63.00 -37.00   0.50    0.05    -- -100.00  57.00 -30.00   52
 21  ω    -59.00 -29.00   0.50    0.05    -- -100.00  57.00  90.00   60
 22  ω     37.00  98.00   0.50    0.05    --  107.75 -94.00 126.00  122
 23  ω     77.00 102.00   0.50    0.05    --  107.75 -77.00 -30.00   50
 24  ω     37.00  69.00   0.50    0.05    --  107.75 -99.00  60.00   64
 25  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00-180.00   50
 26  ω     80.00 105.00   0.50    0.05    --  107.75 -99.00  60.00   50
 27  ω     36.00  63.00   0.50    0.05    --  107.75 -57.00  60.00   54
 28  ω    -24.00   1.00   0.50    0.05    --   47.57 -94.00 127.00   50
 29  ω    -90.00 -24.00   0.50    0.05    --  -47.57 125.00 -60.00  132
 30  ω    -23.00  21.00   0.50    0.05    --   47.57 -19.00  90.00   88
 31  ω    -17.00  13.00   0.50    0.05    --   47.57 -19.00 -60.00   60
 32  ω     49.00  75.00   0.50    0.05    --   47.57 -94.00 127.00   52
 33  ω     -4.00  35.00   0.50    0.05    --   47.57 -37.00 150.00   78
 34  ω    -17.00  12.00   0.50    0.05    --   47.57 -19.00  60.00   58
 35  ω   -127.00 -95.00   0.50    0.05    -- -100.00 146.00  50.43   64
 36  ω   -140.00 -87.00   0.50    0.05    -- -100.00 -37.00-180.00  106
 37  ω   -108.00 -71.00   0.50    0.05    -- -100.00 111.00-116.12   74
 38  ω   -107.00 -70.00   0.50    0.05    -- -100.00 125.00  30.00   74
 39  ω    -87.00 -49.00   0.50    0.05    -- -100.00 125.00-120.00   76
 40  ω   -173.00-133.00   0.50    0.05    -- -100.00 -19.00  60.00   80
 41  ω   -169.00 -87.00   0.50    0.05    -- -100.00 -37.00   0.00  164
 42  ω    -68.00 -42.00   0.50    0.05    -- -100.00 111.00-116.12   52
 43  ω   -121.00 -87.00   0.50    0.05    -- -100.00 138.00-106.71   68
 44  ω   -126.00 -87.00   0.50    0.05    -- -100.00 -19.00  60.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0592542000
_diffrn_orient_matrix_UB_12      0.0407399000
_diffrn_orient_matrix_UB_13      -0.0866866000
_diffrn_orient_matrix_UB_21      0.2050675000
_diffrn_orient_matrix_UB_22      0.0107299000
_diffrn_orient_matrix_UB_23      -0.0045582000
_diffrn_orient_matrix_UB_31      -0.0021124000
_diffrn_orient_matrix_UB_32      -0.1027664000
_diffrn_orient_matrix_UB_33      -0.0348578000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3215
_reflns_number_total             3410
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.053
_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)+(0.0500P)²+0.4577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15),
 C18(H18), C20(H20)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
F1 F 0.86142(11) 0.49895(6) 0.70552(4) 0.0459(2) Uani 1 1 d . . . . .
O1 O 0.51319(13) 0.62436(6) 0.15659(5) 0.0402(2) Uani 1 1 d . . . . .
N1 N 0.64768(13) 0.40738(7) 0.43159(6) 0.0300(2) Uani 1 1 d . . . . .
N2 N 0.99077(13) 0.31959(7) 0.43065(6) 0.0299(2) Uani 1 1 d . . . . .
C1 C 0.32090(15) 0.57013(8) 0.03443(6) 0.0280(2) Uani 1 1 d . . . . .
C2 C 0.32001(17) 0.66094(8) -0.00144(7) 0.0329(3) Uani 1 1 d . . . . .
H2 H 0.386507 0.712542 0.028522 0.040 Uiso 1 1 calc R U . . .
C3 C 0.22315(18) 0.67648(9) -0.08023(7) 0.0358(3) Uani 1 1 d . . . . .
H3 H 0.222910 0.738628 -0.103926 0.043 Uiso 1 1 calc R U . . .
C4 C 0.12627(17) 0.60137(9) -0.12474(7) 0.0340(3) Uani 1 1 d . . . . .
H4 H 0.058783 0.612248 -0.178611 0.041 Uiso 1 1 calc R U . . .
C5 C 0.12840(16) 0.51065(9) -0.09034(7) 0.0336(3) Uani 1 1 d . . . . .
H5 H 0.063890 0.458968 -0.120989 0.040 Uiso 1 1 calc R U . . .
C6 C 0.22462(16) 0.49498(8) -0.01113(7) 0.0311(3) Uani 1 1 d . . . . .
H6 H 0.224900 0.432633 0.012213 0.037 Uiso 1 1 calc R U . . .
C7 C 0.42366(15) 0.55767(8) 0.12059(7) 0.0290(2) Uani 1 1 d . . . . .
C8 C 0.41256(16) 0.46183(8) 0.16197(7) 0.0300(2) Uani 1 1 d . . . . .
H8A H 0.447416 0.409793 0.127933 0.036 Uiso 1 1 calc R U . . .
H8B H 0.283018 0.450415 0.166717 0.036 Uiso 1 1 calc R U . . .
C9 C 0.53830(16) 0.45730(8) 0.24590(7) 0.0301(2) Uani 1 1 d . . . . .
H9A H 0.509725 0.512575 0.278291 0.036 Uiso 1 1 calc R U . . .
H9B H 0.668478 0.464126 0.240447 0.036 Uiso 1 1 calc R U . . .
C10 C 0.51987(17) 0.36398(8) 0.29200(7) 0.0329(3) Uani 1 1 d . . . . .
H10A H 0.397396 0.361838 0.306911 0.039 Uiso 1 1 calc R U . . .
H10B H 0.529592 0.307641 0.257112 0.039 Uiso 1 1 calc R U . . .
C11 C 0.67180(16) 0.36031(8) 0.36755(7) 0.0296(2) Uani 1 1 d . . . . .
C12 C 0.83992(16) 0.31249(8) 0.36433(7) 0.0302(2) Uani 1 1 d . . . . .
C13 C 0.89724(18) 0.25974(9) 0.30429(7) 0.0363(3) Uani 1 1 d . . . . .
H13 H 0.823293 0.242448 0.252964 0.044 Uiso 1 1 calc R U . . .
C14 C 1.0835(2) 0.23678(9) 0.33319(8) 0.0416(3) Uani 1 1 d . . . . .
H14 H 1.159334 0.201596 0.304494 0.050 Uiso 1 1 calc R U . . .
C15 C 1.13848(18) 0.27355(9) 0.40993(8) 0.0382(3) Uani 1 1 d . . . . .
H15 H 1.259118 0.268092 0.443356 0.046 Uiso 1 1 calc R U . . .
C16 C 0.96858(15) 0.36555(7) 0.50248(7) 0.0282(2) Uani 1 1 d . . . . .
C17 C 0.79361(16) 0.40865(8) 0.49961(7) 0.0281(2) Uani 1 1 d . . . . .
C18 C 0.75753(16) 0.45521(8) 0.56838(7) 0.0313(3) Uani 1 1 d . . . . .
H18 H 0.641864 0.485845 0.566953 0.038 Uiso 1 1 calc R U . . .
C19 C 0.89344(17) 0.45526(8) 0.63744(7) 0.0332(3) Uani 1 1 d . . . . .
C20 C 1.06369(17) 0.41238(8) 0.64225(7) 0.0335(3) Uani 1 1 d . . . . .
H20 H 1.152850 0.413704 0.692055 0.040 Uiso 1 1 calc R U . . .
C21 C 1.10626(16) 0.36724(8) 0.57503(7) 0.0315(3) Uani 1 1 d . . . . .
C22 C 1.29608(19) 0.32252(10) 0.58592(9) 0.0449(3) Uani 1 1 d . . . . .
H22A H 1.283642 0.253920 0.571892 0.067 Uiso 1 1 calc R U . . .
H22B H 1.362114 0.329560 0.642570 0.067 Uiso 1 1 calc R U . . .
H22C H 1.365820 0.355017 0.550364 0.067 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 C19 1.3628(13) . ?
O1 C7 1.2204(14) . ?
N1 C11 1.3062(15) . ?
N1 C17 1.3958(14) . ?
N2 C12 1.4030(14) . ?
N2 C15 1.3727(16) . ?
N2 C16 1.4090(15) . ?
C1 C2 1.3967(16) . ?
C1 C6 1.3958(16) . ?
C1 C7 1.4981(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3843(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3894(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3842(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3892(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.5117(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5187(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5309(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5075(15) . ?
C11 C12 1.4193(17) . ?
C12 C13 1.3868(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3945(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3690(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.4155(16) . ?
C16 C21 1.4137(15) . ?
C17 C18 1.4018(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.3650(16) . ?
C19 C20 1.3779(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.3886(17) . ?
C21 C22 1.5082(17) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C11 N1 C17 117.87(10) . . ?
C12 N2 C16 119.88(10) . . ?
C15 N2 C12 107.66(10) . . ?
C15 N2 C16 132.42(10) . . ?
C2 C1 C7 118.58(10) . . ?
C6 C1 C2 118.71(10) . . ?
C6 C1 C7 122.70(10) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.63(11) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.15(11) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.80(11) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.17(11) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.52(11) . . ?
C5 C6 H6 119.7 . . ?
O1 C7 C1 120.20(10) . . ?
O1 C7 C8 120.94(10) . . ?
C1 C7 C8 118.86(9) . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C7 C8 C9 112.56(9) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C8 C9 C10 113.89(9) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 C9 109.06(9) . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
N1 C11 C10 118.22(10) . . ?
N1 C11 C12 122.73(10) . . ?
C12 C11 C10 118.86(10) . . ?
N2 C12 C11 119.26(10) . . ?
C13 C12 N2 107.72(10) . . ?
C13 C12 C11 132.93(11) . . ?
C12 C13 H13 126.3 . . ?
C12 C13 C14 107.34(11) . . ?
C14 C13 H13 126.3 . . ?
C13 C14 H14 125.8 . . ?
C15 C14 C13 108.42(12) . . ?
C15 C14 H14 125.8 . . ?
N2 C15 H15 125.6 . . ?
C14 C15 N2 108.84(11) . . ?
C14 C15 H15 125.6 . . ?
N2 C16 C17 115.80(10) . . ?
N2 C16 C21 123.83(10) . . ?
C21 C16 C17 120.34(10) . . ?
N1 C17 C16 124.17(10) . . ?
N1 C17 C18 115.81(10) . . ?
C18 C17 C16 120.02(10) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 C17 118.07(11) . . ?
C19 C18 H18 121.0 . . ?
F1 C19 C18 119.35(11) . . ?
F1 C19 C20 117.61(10) . . ?
C18 C19 C20 123.04(11) . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.67(10) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C22 125.19(11) . . ?
C20 C21 C16 117.84(11) . . ?
C20 C21 C22 116.96(11) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 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
F1 C19 C20 C21 -179.47(10) . . . . ?
O1 C7 C8 C9 -6.17(16) . . . . ?
N1 C11 C12 N2 -3.38(17) . . . . ?
N1 C11 C12 C13 -179.45(12) . . . . ?
N1 C17 C18 C19 177.57(10) . . . . ?
N2 C12 C13 C14 -1.38(13) . . . . ?
N2 C16 C17 N1 0.23(15) . . . . ?
N2 C16 C17 C18 179.31(10) . . . . ?
N2 C16 C21 C20 -177.83(10) . . . . ?
N2 C16 C21 C22 1.25(18) . . . . ?
C1 C2 C3 C4 -0.36(18) . . . . ?
C1 C7 C8 C9 174.46(9) . . . . ?
C2 C1 C6 C5 -0.62(17) . . . . ?
C2 C1 C7 O1 -4.21(16) . . . . ?
C2 C1 C7 C8 175.16(10) . . . . ?
C2 C3 C4 C5 -0.65(19) . . . . ?
C3 C4 C5 C6 1.01(18) . . . . ?
C4 C5 C6 C1 -0.37(18) . . . . ?
C6 C1 C2 C3 0.98(17) . . . . ?
C6 C1 C7 O1 176.44(11) . . . . ?
C6 C1 C7 C8 -4.20(16) . . . . ?
C7 C1 C2 C3 -178.40(11) . . . . ?
C7 C1 C6 C5 178.73(11) . . . . ?
C7 C8 C9 C10 175.75(10) . . . . ?
C8 C9 C10 C11 170.63(10) . . . . ?
C9 C10 C11 N1 82.10(13) . . . . ?
C9 C10 C11 C12 -93.07(12) . . . . ?
C10 C11 C12 N2 171.56(10) . . . . ?
C10 C11 C12 C13 -4.52(19) . . . . ?
C11 N1 C17 C16 2.71(16) . . . . ?
C11 N1 C17 C18 -176.41(10) . . . . ?
C11 C12 C13 C14 175.03(12) . . . . ?
C12 N2 C15 C14 -0.88(14) . . . . ?
C12 N2 C16 C17 -4.73(14) . . . . ?
C12 N2 C16 C21 173.06(10) . . . . ?
C12 C13 C14 C15 0.85(15) . . . . ?
C13 C14 C15 N2 0.02(15) . . . . ?
C15 N2 C12 C11 -175.58(10) . . . . ?
C15 N2 C12 C13 1.40(13) . . . . ?
C15 N2 C16 C17 177.77(11) . . . . ?
C15 N2 C16 C21 -4.45(19) . . . . ?
C16 N2 C12 C11 6.35(15) . . . . ?
C16 N2 C12 C13 -176.67(9) . . . . ?
C16 N2 C15 C14 176.86(11) . . . . ?
C16 C17 C18 C19 -1.58(16) . . . . ?
C17 N1 C11 C10 -176.05(9) . . . . ?
C17 N1 C11 C12 -1.08(16) . . . . ?
C17 C16 C21 C20 -0.14(16) . . . . ?
C17 C16 C21 C22 178.93(11) . . . . ?
C17 C18 C19 F1 -179.20(10) . . . . ?
C17 C18 C19 C20 0.44(18) . . . . ?
C18 C19 C20 C21 0.88(18) . . . . ?
C19 C20 C21 C16 -1.00(17) . . . . ?
C19 C20 C21 C22 179.84(11) . . . . ?
C21 C16 C17 N1 -177.63(10) . . . . ?
C21 C16 C17 C18 1.45(16) . . . . ?

_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 2.600
_oxdiff_exptl_absorpt_empirical_full_min 0.364
