# 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_d3-0321_auto
_database_code_depnum_ccdc_archive 'CCDC 2250252'
loop_
_audit_author_name
_audit_author_address
'Li xiaoyong'
;nwnu
China
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-21
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 F4 N6'
_chemical_formula_sum            'C23 H26 F4 N6'
_chemical_formula_weight         462.50
_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'

_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                   9.52305(17)
_cell_length_b                   13.1270(2)
_cell_length_c                   18.3358(3)
_cell_angle_alpha                84.4953(15)
_cell_angle_beta                 88.2625(15)
_cell_angle_gamma                89.6565(15)
_cell_volume                     2280.51(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15631
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.1840
_cell_measurement_theta_min      2.3970
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (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    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26437
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.349
_diffrn_reflns_theta_min         2.422
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.942
_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  54.00   0.50    0.05    --   44.32  57.00 -60.00   56
  2  ω     69.00 118.00   0.50    0.05    --   44.32  57.00 -60.00   98
  3  ω    138.00 164.00   0.50    0.20    --  109.62  30.00-180.00   52
  4  ω    148.00 173.00   0.50    0.20    --  109.62  45.00-120.00   50
  5  ω    100.00 144.00   0.50    0.20    --  109.62  45.00-120.00   88
  6  ω    -26.00  22.00   0.50    0.05    --   44.32 -19.00-150.00   96
  7  ω    -31.00  11.00   0.50    0.05    --   44.32 -19.00 -90.00   84
  8  ω    -23.00   2.00   0.50    0.05    --   44.32 -19.00 -60.00   50
  9  ω    -18.00  19.00   0.50    0.05    --   44.32 -19.00   0.00   74
 10  ω    -30.00  36.00   0.50    0.05    --   44.32 -37.00 150.00  132
 11  ω     37.00  72.00   0.50    0.20    --  109.62 -94.00  60.00   70
 12  ω     59.00 109.00   0.50    0.20    --  109.62-125.00   0.00  100
 13  ω     38.00  82.00   0.50    0.05    --   44.32-108.00-174.00   88
 14  ω      9.00  35.00   0.50    0.05    --   44.32-108.00-174.00   52
 15  ω     82.00 107.00   0.50    0.20    --  109.62-108.00-174.00   50
 16  ω     72.00 103.00   0.50    0.20    --  109.62 -77.00-180.00   62
 17  ω     40.00  68.00   0.50    0.20    --  109.62 -61.00-120.00   56
 18  ω     37.00  67.00   0.50    0.20    --  109.62 -61.00 -90.00   60
 19  ω     69.00  95.00   0.50    0.20    --  109.62 -77.00 -30.00   52
 20  ω     40.00  89.00   0.50    0.20    --  109.62 -77.00   0.00   98
 21  ω     39.00  65.00   0.50    0.20    --  109.62 -77.00 -30.00   52
 22  ω     91.00 124.00   0.50    0.20    --  109.62 108.00 -77.00   66
 23  ω    128.00 167.00   0.50    0.20    --  109.62 108.00 -77.00   78
 24  ω    100.00 175.00   0.50    0.20    --  109.62 125.00-120.00  150
 25  ω     49.00 119.00   0.50    0.05    --   44.32 179.00  90.00  140
 26  ω    -74.00 -28.00   0.50    0.20    -- -100.00  61.00  30.00   92
 27  ω    -53.00 -28.00   0.50    0.20    -- -100.00  45.00  30.00   50
 28  ω    -74.00 -38.00   0.50    0.20    -- -100.00  61.00 -60.00   72
 29  ω    -54.00 -29.00   0.50    0.20    -- -100.00  45.00 -90.00   50
 30  ω    -54.00 -25.00   0.50    0.20    -- -100.00  45.00-120.00   58
 31  ω    -70.00 -26.00   0.50    0.20    -- -100.00  61.00-180.00   88
 32  ω   -107.00 -71.00   0.50    0.20    -- -100.00 108.00 -77.00   72
 33  ω   -112.00 -54.00   0.50    0.20    -- -100.00 125.00 -90.00  116
 34  ω   -121.00 -95.00   0.50    0.20    -- -100.00 140.00  15.41   52
 35  ω   -106.00 -40.00   0.50    0.20    -- -100.00 125.00 150.00  132
 36  ω   -107.00 -60.00   0.50    0.20    -- -100.00 125.00  90.00   94
 37  ω   -109.00 -27.00   0.50    0.20    -- -100.00 115.00  59.71  164
 38  ω    -59.00 -33.00   0.50    0.20    -- -100.00 140.00  15.41   52
 39  ω    -73.00 -48.00   0.50    0.05    --  -44.32 108.00 -77.00   50
 40  ω   -143.00 -70.00   0.50    0.20    -- -100.00 -15.00 -90.00  146
 41  ω   -177.00 -80.00   0.50    0.20    -- -100.00 -30.00  30.00  194
 42  ω   -164.00-139.00   0.50    0.20    -- -100.00 -61.00 -90.00   50
 43  ω   -134.00 -80.00   0.50    0.20    -- -100.00 -61.00 -90.00  108
 44  ω   -120.00 -90.00   0.50    0.20    -- -100.00-108.00-174.00   60
 45  ω   -167.00-144.50   0.50    0.20    -- -100.00-125.00  90.00   45
;
_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      -0.0528719000
_diffrn_orient_matrix_UB_12      -0.0952898000
_diffrn_orient_matrix_UB_13      0.0484034000
_diffrn_orient_matrix_UB_21      0.0728161000
_diffrn_orient_matrix_UB_22      0.0377067000
_diffrn_orient_matrix_UB_23      0.0662781000
_diffrn_orient_matrix_UB_31      -0.1345246000
_diffrn_orient_matrix_UB_32      0.0583016000
_diffrn_orient_matrix_UB_33      0.0198876000
_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                7855
_reflns_number_total             9012
_reflns_odcompleteness_completeness 99.79
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00210(19)
_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   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         9012
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0406
_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)+(0.0512P)²+0.7138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1091
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C12(H12), C21(H21), C26(H26), C28(H28), C29(H29), C32(H32)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C42(H42),
  C43(H43), C44(H44), C45(H45), C46(H46)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C34(H34A,
 H34B,H34C)
;
_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 0.51591(11) 0.39802(8) 0.07517(6) 0.0512(3) Uani 1 1 d . . . . .
F2 F 0.29365(10) 0.38765(7) 0.10440(5) 0.0428(2) Uani 1 1 d . . . . .
F3 F 0.72838(11) -0.16159(8) 0.23927(7) 0.0533(3) Uani 1 1 d . . . . .
F4 F 0.60375(12) -0.17043(7) 0.14387(5) 0.0482(2) Uani 1 1 d . . . . .
N1 N 0.53087(13) 0.19431(9) 0.27056(7) 0.0300(3) Uani 1 1 d . . . . .
N2 N 0.50870(13) 0.29429(9) 0.24120(7) 0.0306(3) Uani 1 1 d . . . . .
N3 N 0.42984(12) 0.18751(8) 0.16373(6) 0.0264(2) Uani 1 1 d . . . . .
N4 N 0.36904(12) 0.04834(9) 0.25841(7) 0.0292(3) Uani 1 1 d . . . . .
N5 N 0.40919(12) -0.05385(8) 0.25940(7) 0.0294(3) Uani 1 1 d . . . . .
N6 N 0.58094(12) 0.04360(9) 0.20403(7) 0.0283(2) Uani 1 1 d . . . . .
C1 C 0.47735(14) 0.11878(10) 0.22556(8) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.45066(14) 0.28639(10) 0.17916(8) 0.0280(3) Uani 1 1 d . . . . .
C3 C 0.42311(16) 0.38385(11) 0.13376(9) 0.0354(3) Uani 1 1 d . . . . .
H3 H 0.432256 0.441967 0.164779 0.043 Uiso 1 1 calc R . . . .
C4 C 0.53131(14) -0.05231(10) 0.22678(8) 0.0277(3) Uani 1 1 d . . . . .
C5 C 0.59524(15) -0.15398(11) 0.21612(8) 0.0318(3) Uani 1 1 d . . . . .
H5 H 0.537005 -0.209004 0.243519 0.038 Uiso 1 1 calc R . . . .
C6 C 0.57893(15) 0.17666(12) 0.34241(8) 0.0313(3) Uani 1 1 d . . . . .
C7 C 0.58785(17) 0.07840(13) 0.37823(9) 0.0398(4) Uani 1 1 d . . . . .
H7 H 0.560019 0.020977 0.354381 0.048 Uiso 1 1 calc R . . . .
C8 C 0.63750(18) 0.06476(15) 0.44883(9) 0.0463(4) Uani 1 1 d . . . . .
H8 H 0.644107 -0.002396 0.472906 0.056 Uiso 1 1 calc R . . . .
C9 C 0.6776(2) 0.14743(17) 0.48474(10) 0.0515(5) Uani 1 1 d . . . . .
H9 H 0.710234 0.137446 0.533364 0.062 Uiso 1 1 calc R . . . .
C10 C 0.6694(2) 0.24514(16) 0.44876(10) 0.0529(5) Uani 1 1 d . . . . .
H10 H 0.697070 0.302290 0.472964 0.064 Uiso 1 1 calc R . . . .
C11 C 0.62150(18) 0.26031(14) 0.37809(9) 0.0421(4) Uani 1 1 d . . . . .
H11 H 0.617483 0.327467 0.353795 0.050 Uiso 1 1 calc R . . . .
C12 C 0.36088(15) 0.14434(11) 0.10291(8) 0.0303(3) Uani 1 1 d . . . . .
H12 H 0.380825 0.069162 0.108405 0.036 Uiso 1 1 calc R . . . .
C13 C 0.20179(17) 0.15594(12) 0.10653(10) 0.0404(4) Uani 1 1 d . . . . .
H13A H 0.166237 0.132224 0.155923 0.061 Uiso 1 1 calc GR . . . .
H13B H 0.160100 0.114977 0.070855 0.061 Uiso 1 1 calc GR . . . .
H13C H 0.176595 0.228079 0.095137 0.061 Uiso 1 1 calc GR . . . .
C14 C 0.4225(2) 0.18534(14) 0.02831(9) 0.0441(4) Uani 1 1 d . . . . .
H14A H 0.392635 0.256514 0.016950 0.066 Uiso 1 1 calc GR . . . .
H14B H 0.389366 0.143764 -0.009288 0.066 Uiso 1 1 calc GR . . . .
H14C H 0.525324 0.182137 0.029253 0.066 Uiso 1 1 calc GR . . . .
C15 C 0.25601(14) 0.07452(10) 0.30469(7) 0.0270(3) Uani 1 1 d . . . . .
C16 C 0.17829(15) -0.00297(11) 0.34445(8) 0.0315(3) Uani 1 1 d . . . . .
H16 H 0.201389 -0.072707 0.340237 0.038 Uiso 1 1 calc R . . . .
C17 C 0.06764(17) 0.02206(13) 0.38994(9) 0.0404(4) Uani 1 1 d . . . . .
H17 H 0.015345 -0.030981 0.417049 0.048 Uiso 1 1 calc R . . . .
C18 C 0.03170(17) 0.12322(13) 0.39669(9) 0.0389(4) Uani 1 1 d . . . . .
H18 H -0.044313 0.139757 0.428236 0.047 Uiso 1 1 calc R . . . .
C19 C 0.10818(16) 0.19961(12) 0.35680(8) 0.0337(3) Uani 1 1 d . . . . .
H19 H 0.084209 0.269181 0.361101 0.040 Uiso 1 1 calc R . . . .
C20 C 0.21917(15) 0.17656(11) 0.31065(8) 0.0317(3) Uani 1 1 d . . . . .
H20 H 0.270087 0.229966 0.283133 0.038 Uiso 1 1 calc R . . . .
C21 C 0.71776(15) 0.08021(11) 0.17138(9) 0.0345(3) Uani 1 1 d . . . . .
H21 H 0.706357 0.155340 0.157754 0.041 Uiso 1 1 calc R . . . .
C22 C 0.83626(17) 0.06885(14) 0.22529(11) 0.0465(4) Uani 1 1 d . . . . .
H22A H 0.810160 0.103294 0.268863 0.070 Uiso 1 1 calc GR . . . .
H22B H 0.921869 0.099879 0.202150 0.070 Uiso 1 1 calc GR . . . .
H22C H 0.853156 -0.003934 0.239618 0.070 Uiso 1 1 calc GR . . . .
C23 C 0.75489(18) 0.03332(14) 0.10049(10) 0.0441(4) Uani 1 1 d . . . . .
H23A H 0.780532 -0.038771 0.111702 0.066 Uiso 1 1 calc GR . . . .
H23B H 0.834344 0.070298 0.075389 0.066 Uiso 1 1 calc GR . . . .
H23C H 0.673705 0.038241 0.068736 0.066 Uiso 1 1 calc GR . . . .
F5 F 1.05555(11) -0.09257(8) 0.07908(6) 0.0503(3) Uani 1 1 d . . . . .
F6 F 1.27270(10) -0.11125(7) 0.11028(5) 0.0420(2) Uani 1 1 d . . . . .
F7 F 0.96046(12) -0.65689(8) 0.12873(6) 0.0547(3) Uani 1 1 d . . . . .
F8 F 0.81669(10) -0.65955(8) 0.22235(8) 0.0601(3) Uani 1 1 d . . . . .
N7 N 1.00473(12) -0.30422(9) 0.26988(7) 0.0282(2) Uani 1 1 d . . . . .
N8 N 1.03425(12) -0.20387(9) 0.24285(7) 0.0296(3) Uani 1 1 d . . . . .
N9 N 1.12027(12) -0.30869(8) 0.16332(6) 0.0253(2) Uani 1 1 d . . . . .
N10 N 1.16724(12) -0.45109(8) 0.25684(7) 0.0270(2) Uani 1 1 d . . . . .
N11 N 1.12954(12) -0.55260(8) 0.25319(7) 0.0284(2) Uani 1 1 d . . . . .
N12 N 0.96404(11) -0.45169(8) 0.19988(7) 0.0274(2) Uani 1 1 d . . . . .
C24 C 1.06443(13) -0.37875(10) 0.22393(7) 0.0248(3) Uani 1 1 d . . . . .
C25 C 1.10043(14) -0.21042(10) 0.18114(8) 0.0277(3) Uani 1 1 d . . . . .
C26 C 1.13873(17) -0.11182(11) 0.13823(9) 0.0364(3) Uani 1 1 d . . . . .
H26 H 1.127243 -0.054997 0.170567 0.044 Uiso 1 1 calc R . . . .
C27 C 1.01212(14) -0.54871(10) 0.21942(8) 0.0274(3) Uani 1 1 d . . . . .
C28 C 0.95355(16) -0.64839(11) 0.20258(9) 0.0356(3) Uani 1 1 d . . . . .
H28 H 1.008613 -0.705393 0.228317 0.043 Uiso 1 1 calc R . . . .
C29 C 0.83070(15) -0.41249(11) 0.16842(9) 0.0354(3) Uani 1 1 d . . . . .
H29 H 0.841591 -0.336628 0.158805 0.042 Uiso 1 1 calc R . . . .
C30 C 0.70571(16) -0.43023(14) 0.22172(11) 0.0458(4) Uani 1 1 d . . . . .
H30A H 0.688800 -0.503883 0.231725 0.069 Uiso 1 1 calc GR . . . .
H30B H 0.622220 -0.397001 0.200174 0.069 Uiso 1 1 calc GR . . . .
H30C H 0.725615 -0.401232 0.267601 0.069 Uiso 1 1 calc GR . . . .
C31 C 0.80394(19) -0.45187(15) 0.09472(10) 0.0485(4) Uani 1 1 d . . . . .
H31A H 0.889368 -0.444247 0.063551 0.073 Uiso 1 1 calc GR . . . .
H31B H 0.727436 -0.412447 0.070926 0.073 Uiso 1 1 calc GR . . . .
H31C H 0.777763 -0.524290 0.102219 0.073 Uiso 1 1 calc GR . . . .
C32 C 1.19975(15) -0.35063(11) 0.10260(8) 0.0291(3) Uani 1 1 d . . . . .
H32 H 1.174282 -0.424656 0.104533 0.035 Uiso 1 1 calc R . . . .
C33 C 1.15789(18) -0.30190(13) 0.02771(9) 0.0406(4) Uani 1 1 d . . . . .
H33A H 1.055323 -0.302218 0.024701 0.061 Uiso 1 1 calc GR . . . .
H33B H 1.199494 -0.340876 -0.010551 0.061 Uiso 1 1 calc GR . . . .
H33C H 1.191887 -0.231217 0.020732 0.061 Uiso 1 1 calc GR . . . .
C34 C 1.35779(15) -0.34678(12) 0.11215(9) 0.0345(3) Uani 1 1 d . . . . .
H34A H 1.388830 -0.275343 0.107110 0.052 Uiso 1 1 calc GR . . . .
H34B H 1.405727 -0.383765 0.074601 0.052 Uiso 1 1 calc GR . . . .
H34C H 1.380576 -0.378764 0.160879 0.052 Uiso 1 1 calc GR . . . .
C35 C 0.94923(14) -0.32423(11) 0.34173(8) 0.0302(3) Uani 1 1 d . . . . .
C36 C 0.93185(16) -0.42374(12) 0.37468(9) 0.0375(3) Uani 1 1 d . . . . .
H36 H 0.959004 -0.480412 0.348840 0.045 Uiso 1 1 calc R . . . .
C37 C 0.87482(18) -0.43966(15) 0.44524(9) 0.0450(4) Uani 1 1 d . . . . .
H37 H 0.863008 -0.507562 0.467524 0.054 Uiso 1 1 calc R . . . .
C38 C 0.8349(2) -0.35811(17) 0.48368(9) 0.0509(4) Uani 1 1 d . . . . .
H38 H 0.796626 -0.369625 0.532208 0.061 Uiso 1 1 calc R . . . .
C39 C 0.8513(2) -0.25944(16) 0.45054(10) 0.0518(5) Uani 1 1 d . . . . .
H39 H 0.823434 -0.203105 0.476557 0.062 Uiso 1 1 calc R . . . .
C40 C 0.90782(18) -0.24170(13) 0.38007(9) 0.0403(4) Uani 1 1 d . . . . .
H40 H 0.918365 -0.173650 0.357889 0.048 Uiso 1 1 calc R . . . .
C41 C 1.27297(13) -0.42820(10) 0.30490(7) 0.0254(3) Uani 1 1 d . . . . .
C42 C 1.30856(15) -0.32712(11) 0.31369(8) 0.0303(3) Uani 1 1 d . . . . .
H42 H 1.262020 -0.272251 0.286623 0.036 Uiso 1 1 calc R . . . .
C43 C 1.41208(15) -0.30692(12) 0.36205(8) 0.0323(3) Uani 1 1 d . . . . .
H43 H 1.434735 -0.237993 0.368364 0.039 Uiso 1 1 calc R . . . .
C44 C 1.48255(16) -0.38554(13) 0.40108(9) 0.0383(3) Uani 1 1 d . . . . .
H44 H 1.553527 -0.371235 0.433912 0.046 Uiso 1 1 calc R . . . .
C45 C 1.44787(17) -0.48584(13) 0.39150(9) 0.0398(4) Uani 1 1 d . . . . .
H45 H 1.495780 -0.540411 0.418148 0.048 Uiso 1 1 calc R . . . .
C46 C 1.34465(15) -0.50778(11) 0.34377(8) 0.0309(3) Uani 1 1 d . . . . .
H46 H 1.322775 -0.576869 0.337548 0.037 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.3697(19) . ?
F2 C3 1.3589(18) . ?
F3 C5 1.3493(18) . ?
F4 C5 1.3624(18) . ?
N1 N2 1.3874(16) . ?
N1 C1 1.4534(17) . ?
N1 C6 1.4055(19) . ?
N2 C2 1.2929(19) . ?
N3 C1 1.4608(17) . ?
N3 C2 1.3716(17) . ?
N3 C12 1.4717(18) . ?
N4 N5 1.3913(16) . ?
N4 C1 1.4658(17) . ?
N4 C15 1.4117(17) . ?
N5 C4 1.2908(18) . ?
N6 C1 1.4636(17) . ?
N6 C4 1.3701(18) . ?
N6 C21 1.4805(18) . ?
C2 C3 1.484(2) . ?
C4 C5 1.4910(18) . ?
C6 C7 1.393(2) . ?
C6 C11 1.399(2) . ?
C7 C8 1.387(2) . ?
C8 C9 1.384(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.383(2) . ?
C12 C13 1.522(2) . ?
C12 C14 1.523(2) . ?
C15 C16 1.396(2) . ?
C15 C20 1.396(2) . ?
C16 C17 1.382(2) . ?
C17 C18 1.385(2) . ?
C18 C19 1.381(2) . ?
C19 C20 1.384(2) . ?
C21 C22 1.520(2) . ?
C21 C23 1.522(2) . ?
F5 C26 1.3654(19) . ?
F6 C26 1.3602(18) . ?
F7 C28 1.369(2) . ?
F8 C28 1.3472(18) . ?
N7 N8 1.3894(16) . ?
N7 C24 1.4535(17) . ?
N7 C35 1.4061(19) . ?
N8 C25 1.2883(19) . ?
N9 C24 1.4621(17) . ?
N9 C25 1.3714(17) . ?
N9 C32 1.4754(17) . ?
N10 N11 1.3904(16) . ?
N10 C24 1.4625(17) . ?
N10 C41 1.4104(17) . ?
N11 C27 1.2930(18) . ?
N12 C24 1.4637(17) . ?
N12 C27 1.3695(17) . ?
N12 C29 1.4797(17) . ?
C25 C26 1.490(2) . ?
C27 C28 1.4884(19) . ?
C29 C30 1.522(2) . ?
C29 C31 1.521(2) . ?
C32 C33 1.522(2) . ?
C32 C34 1.522(2) . ?
C35 C36 1.394(2) . ?
C35 C40 1.396(2) . ?
C36 C37 1.386(2) . ?
C37 C38 1.382(3) . ?
C38 C39 1.385(3) . ?
C39 C40 1.384(2) . ?
C41 C42 1.3968(19) . ?
C41 C46 1.3941(19) . ?
C42 C43 1.389(2) . ?
C43 C44 1.381(2) . ?
C44 C45 1.388(2) . ?
C45 C46 1.385(2) . ?

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
N2 N1 C1 113.11(11) . . ?
N2 N1 C6 118.96(12) . . ?
C6 N1 C1 127.07(12) . . ?
C2 N2 N1 105.10(11) . . ?
C1 N3 C12 119.27(11) . . ?
C2 N3 C1 108.35(11) . . ?
C2 N3 C12 132.11(12) . . ?
N5 N4 C1 112.80(10) . . ?
N5 N4 C15 118.83(11) . . ?
C15 N4 C1 125.65(11) . . ?
C4 N5 N4 105.11(11) . . ?
C1 N6 C21 118.91(11) . . ?
C4 N6 C1 108.41(11) . . ?
C4 N6 C21 132.30(11) . . ?
N1 C1 N3 99.12(10) . . ?
N1 C1 N4 117.59(11) . . ?
N1 C1 N6 114.90(11) . . ?
N3 C1 N4 114.08(11) . . ?
N3 C1 N6 113.03(11) . . ?
N6 C1 N4 98.96(10) . . ?
N2 C2 N3 114.18(12) . . ?
N2 C2 C3 116.19(12) . . ?
N3 C2 C3 129.55(13) . . ?
F1 C3 C2 111.54(12) . . ?
F2 C3 F1 105.33(12) . . ?
F2 C3 C2 113.09(12) . . ?
N5 C4 N6 114.63(12) . . ?
N5 C4 C5 116.11(12) . . ?
N6 C4 C5 129.20(12) . . ?
F3 C5 F4 105.32(12) . . ?
F3 C5 C4 112.18(12) . . ?
F4 C5 C4 111.48(12) . . ?
C7 C6 N1 121.88(14) . . ?
C7 C6 C11 119.38(15) . . ?
C11 C6 N1 118.73(14) . . ?
C8 C7 C6 119.76(16) . . ?
C9 C8 C7 121.04(17) . . ?
C8 C9 C10 119.08(16) . . ?
C11 C10 C9 120.79(18) . . ?
C10 C11 C6 119.95(17) . . ?
N3 C12 C13 112.84(12) . . ?
N3 C12 C14 112.42(12) . . ?
C13 C12 C14 111.66(14) . . ?
C16 C15 N4 119.46(12) . . ?
C16 C15 C20 119.32(13) . . ?
C20 C15 N4 121.20(12) . . ?
C17 C16 C15 119.80(14) . . ?
C16 C17 C18 121.09(15) . . ?
C19 C18 C17 118.91(14) . . ?
C18 C19 C20 121.13(14) . . ?
C19 C20 C15 119.75(14) . . ?
N6 C21 C22 113.06(13) . . ?
N6 C21 C23 112.36(13) . . ?
C22 C21 C23 112.15(13) . . ?
N8 N7 C24 112.85(11) . . ?
N8 N7 C35 119.23(11) . . ?
C35 N7 C24 126.56(12) . . ?
C25 N8 N7 105.27(11) . . ?
C24 N9 C32 119.22(10) . . ?
C25 N9 C24 108.27(11) . . ?
C25 N9 C32 131.92(12) . . ?
N11 N10 C24 112.80(10) . . ?
N11 N10 C41 119.16(11) . . ?
C41 N10 C24 125.92(11) . . ?
C27 N11 N10 105.21(11) . . ?
C24 N12 C29 118.84(11) . . ?
C27 N12 C24 108.41(10) . . ?
C27 N12 C29 132.38(12) . . ?
N7 C24 N9 99.10(10) . . ?
N7 C24 N10 117.26(11) . . ?
N7 C24 N12 115.10(11) . . ?
N9 C24 N10 114.58(11) . . ?
N9 C24 N12 112.50(11) . . ?
N10 C24 N12 99.11(10) . . ?
N8 C25 N9 114.22(12) . . ?
N8 C25 C26 116.35(12) . . ?
N9 C25 C26 129.37(13) . . ?
F5 C26 C25 111.30(13) . . ?
F6 C26 F5 105.42(13) . . ?
F6 C26 C25 112.88(12) . . ?
N11 C27 N12 114.47(12) . . ?
N11 C27 C28 116.34(12) . . ?
N12 C27 C28 129.04(12) . . ?
F7 C28 C27 110.77(13) . . ?
F8 C28 F7 105.41(13) . . ?
F8 C28 C27 112.97(12) . . ?
N12 C29 C30 112.74(13) . . ?
N12 C29 C31 112.43(13) . . ?
C31 C29 C30 112.07(14) . . ?
N9 C32 C33 112.67(12) . . ?
N9 C32 C34 112.25(11) . . ?
C33 C32 C34 111.88(13) . . ?
C36 C35 N7 121.84(13) . . ?
C36 C35 C40 119.54(14) . . ?
C40 C35 N7 118.60(14) . . ?
C37 C36 C35 119.74(16) . . ?
C38 C37 C36 120.91(17) . . ?
C37 C38 C39 119.15(16) . . ?
C40 C39 C38 120.94(17) . . ?
C39 C40 C35 119.71(17) . . ?
C42 C41 N10 121.23(12) . . ?
C46 C41 N10 119.52(12) . . ?
C46 C41 C42 119.25(13) . . ?
C43 C42 C41 119.93(13) . . ?
C44 C43 C42 120.97(14) . . ?
C43 C44 C45 118.85(14) . . ?
C46 C45 C44 121.17(14) . . ?
C45 C46 C41 119.82(14) . . ?

_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 3.103
_oxdiff_exptl_absorpt_empirical_full_min 0.557
####################################################################### 
# 
# 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_c7_0522_auto
_database_code_depnum_ccdc_archive 'CCDC 2264556'
loop_
_audit_author_name
_audit_author_address
zhouyuxiu
;xibeishifandaxueceshizhongxin
China
;
_audit_update_record             
;
2023-05-22 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;
_audit_creation_date             2023-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 F2 N4'
_chemical_formula_sum            'C13 H16 F2 N4'
_chemical_formula_weight         266.30
_chemical_absolute_configuration unk
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.1731(3)
_cell_length_b                   9.5526(5)
_cell_length_c                   11.6141(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.315(4)
_cell_angle_gamma                90
_cell_volume                     680.72(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5959
_cell_measurement_temperature    301.22(10)
_cell_measurement_theta_max      76.3010
_cell_measurement_theta_min      3.8140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (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    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8813
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.917
_diffrn_reflns_theta_min         3.829
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.22(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    112.00 167.00   0.50    0.07    --  112.00  45.00  90.00  110
  2  ω     61.00 166.00   0.50    0.07    --  112.00  11.00  40.00  210
  3  ω     -6.00 113.00   0.50    0.05    --   45.34  11.00  40.00  238
  4  ω     39.00  65.00   0.50    0.07    --  112.00-125.00-180.00   52
  5  ω     45.00  79.00   0.50    0.07    --  112.00-125.00-150.00   68
  6  ω     83.00 112.00   0.50    0.07    --  112.00-125.00-150.00   58
  7  ω     75.00 106.00   0.50    0.07    --  112.00-125.00-180.00   62
  8  ω     81.00 106.00   0.50    0.07    --  112.00 -94.00-180.00   50
  9  ω     48.00  91.00   0.50    0.07    --  112.00 -94.00 120.00   86
 10  ω    -25.00   1.00   0.50    0.05    --   45.34 -11.00-132.00   52
 11  ω     42.00  87.00   0.50    0.07    --  112.00 -77.00-180.00   90
 12  ω     40.00  68.00   0.50    0.07    --  112.00 -61.00-180.00   56
 13  ω     42.00  67.00   0.50    0.07    --  112.00 -61.00-150.00   50
 14  ω     41.00  67.00   0.50    0.07    --  112.00 -61.00-120.00   52
 15  ω     40.00  66.00   0.50    0.07    --  112.00 -61.00 -90.00   52
 16  ω   -108.00 -75.00   0.50    0.07    -- -100.00  77.00 150.00   66
 17  ω    -66.00 -38.00   0.50    0.07    -- -100.00  77.00 150.00   56
 18  ω    -53.00 -27.00   0.50    0.07    -- -100.00  45.00   0.00   52
 19  ω    -67.00 -37.00   0.50    0.07    -- -100.00  61.00-120.00   60
 20  ω    -52.00 -26.00   0.50    0.07    -- -100.00  45.00-150.00   52
 21  ω    -87.00 -44.00   0.50    0.05    --  -45.34 -11.00-132.00   86
 22  ω   -122.00 -90.00   0.50    0.05    --  -45.34 -11.00-132.00   64
 23  ω   -144.00 -73.00   0.50    0.07    -- -100.00 -11.00-132.00  142
 24  ω   -121.00 -60.00   0.50    0.05    --  -45.34-179.00  30.00  122
 25  ω   -173.00-147.00   0.50    0.07    -- -100.00 -11.00-132.00   52
 26  ω    -58.00 -32.00   0.50    0.05    --  -45.28 -77.00  90.00   52
 27  ω    -61.00 -27.00   0.50    0.05    --  -45.28 -57.00 120.00   68
 28  ω     40.00  67.00   0.50    0.05    --   45.28  37.00  90.00   54
 29  ω     24.00  52.00   0.50    0.05    --   45.28  19.00 150.00   56
 30  ω     29.00  63.00   0.50    0.05    --   45.28  57.00  90.00   68
 31  ω     23.00  48.00   0.50    0.05    --   45.28  77.00-150.00   50
 32  ω     18.00  74.00   0.50    0.05    --   45.28  77.00 150.00  112
 33  ω   -170.00-145.00   0.50    0.07    -- -100.00 -59.00  74.20   50
 34  ω    -98.00 -73.00   0.50    0.07    -- -100.00 -77.00 120.00   50
 35  ω   -101.00 -75.00   0.50    0.07    -- -100.00 -71.00-140.35   52
 36  ω   -122.00 -79.00   0.50    0.07    -- -100.00 -61.00 150.00   86
 37  ω    -99.00 -73.00   0.50    0.07    -- -100.00 -77.00-120.00   52
 38  ω   -108.00 -83.00   0.50    0.07    -- -100.00 -51.00-174.74   50
 39  ω   -141.00-115.00   0.50    0.07    -- -100.00 -77.00-180.00   52
 40  ω   -165.00-139.00   0.50    0.07    -- -100.00 -77.00 120.00   52
 41  ω   -103.00 -77.00   0.50    0.07    -- -100.00 -66.00-176.20   52
 42  ω   -101.00 -73.00   0.50    0.07    -- -100.00 -77.00-150.00   56
 43  ω   -106.00 -80.00   0.50    0.07    -- -100.00 -61.00  90.00   52
 44  ω   -105.00 -73.00   0.50    0.07    -- -100.00 -77.00  60.00   64
 45  ω   -113.00 -88.00   0.50    0.07    -- -100.00 -41.00 134.25   50
 46  ω   -165.00-139.00   0.50    0.07    -- -100.00 -77.00-150.00   52
 47  ω   -160.00-134.00   0.50    0.07    -- -100.00 -61.00 150.00   52
 48  ω   -120.00 -82.00   0.50    0.07    -- -100.00 -61.00 120.00   76
 49  ω   -126.00 -82.00   0.50    0.07    -- -100.00-125.00-120.00   88
 50  ω   -167.00-142.00   0.50    0.07    -- -100.00 -65.00 141.23   50
 51  ω   -129.00 -78.00   0.50    0.07    -- -100.00 -65.00 141.23  102
 52  ω   -104.00 -79.00   0.50    0.07    -- -100.00 -61.00-150.00   50
 53  ω   -105.00 -80.00   0.50    0.07    -- -100.00 -47.00 102.57   50
 54  ω   -106.00 -81.00   0.50    0.07    -- -100.00 -51.00  69.03   50
 55  ω   -105.00 -80.00   0.50    0.07    -- -100.00 -50.00  82.24   50
 56  ω    -99.00 -74.00   0.50    0.07    -- -100.00 -77.00-180.00   50
 57  ω   -105.00 -80.00   0.50    0.07    -- -100.00 -59.00  74.20   50
 58  ω   -172.00-147.00   0.50    0.07    -- -100.00 -45.00-155.60   50
 59  ω   -106.00 -79.00   0.50    0.07    -- -100.00 -45.00-155.60   54
 60  ω   -171.00-146.00   0.50    0.07    -- -100.00 -71.00-140.35   50
 61  ω   -102.00 -77.00   0.50    0.07    -- -100.00 -73.00 163.05   50
 62  ω   -101.00 -76.00   0.50    0.07    -- -100.00 -74.00 141.52   50
 63  ω     86.00 112.00   0.50    0.07    --  112.00  77.00  60.00   52
 64  ω    150.00 175.00   0.50    0.07    --  112.00  77.00 150.00   50
 65  ω     87.00 113.00   0.50    0.07    --  112.00  77.00 150.00   52
 66  ω     39.00  64.00   0.50    0.07    --  112.00 -61.00  60.00   50
;
_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      0.0046061000
_diffrn_orient_matrix_UB_12      0.0166577000
_diffrn_orient_matrix_UB_13      0.1321233000
_diffrn_orient_matrix_UB_21      -0.2496418000
_diffrn_orient_matrix_UB_22      -0.0167027000
_diffrn_orient_matrix_UB_23      -0.0107429000
_diffrn_orient_matrix_UB_31      0.0267422000
_diffrn_orient_matrix_UB_32      -0.1595680000
_diffrn_orient_matrix_UB_33      0.0150962000
_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         0.742
_reflns_Friedel_fraction_full    0.878
_reflns_Friedel_fraction_max     0.811
_reflns_number_gt                2287
_reflns_number_total             2592
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      1.044
_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)+(0.1512P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.1899
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C8(H8), C10(H10), C11(H11), C13(H13)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C)
;
_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 0.0676(6) 0.7833(4) 0.8213(3) 0.1049(10) Uani 1 1 d . . . . .
F2 F 0.3458(8) 0.8824(4) 0.7675(4) 0.1315(16) Uani 1 1 d . . . . .
N1 N 0.2855(5) 0.5771(3) 0.6972(3) 0.0576(7) Uani 1 1 d . . . . .
N2 N 0.3952(5) 0.3602(4) 0.6170(3) 0.0639(8) Uani 1 1 d . . . . .
H2 H 0.494911 0.296939 0.624663 0.077 Uiso 1 1 calc R U . . .
N3 N 0.5251(5) 0.5763(4) 0.8595(3) 0.0635(8) Uani 1 1 d . . . . .
N4 N 0.5504(5) 0.4572(3) 0.7950(2) 0.0575(7) Uani 1 1 d . . . . .
C1 C 0.4056(5) 0.4611(4) 0.6971(3) 0.0533(7) Uani 1 1 d . . . . .
C2 C 0.2881(8) 0.7786(5) 0.8352(4) 0.0738(11) Uani 1 1 d . . . . .
H2A H 0.343703 0.796131 0.916282 0.089 Uiso 1 1 calc R U . . .
C3 C 0.2721(8) 0.2104(5) 0.4581(4) 0.0796(13) Uani 1 1 d . . . . .
H3A H 0.415532 0.212548 0.433576 0.119 Uiso 1 1 calc R U . . .
H3B H 0.166385 0.196736 0.392065 0.119 Uiso 1 1 calc R U . . .
H3C H 0.262626 0.134963 0.511942 0.119 Uiso 1 1 calc R U . . .
C4 C 0.2274(6) 0.3477(4) 0.5163(3) 0.0584(8) Uani 1 1 d . . . . .
C5 C 1.0449(7) 0.1715(6) 0.9022(3) 0.0760(12) Uani 1 1 d . . . . .
H5 H 1.156311 0.108419 0.924689 0.091 Uiso 1 1 calc R U . . .
C6 C 0.7157(5) 0.3585(4) 0.8311(3) 0.0558(8) Uani 1 1 d . . . . .
C7 C 0.2419(8) 0.4687(5) 0.4344(3) 0.0754(11) Uani 1 1 d . . . . .
H7A H 0.217881 0.554711 0.473810 0.113 Uiso 1 1 calc R U . . .
H7B H 0.133211 0.458239 0.369247 0.113 Uiso 1 1 calc R U . . .
H7C H 0.383905 0.470226 0.408031 0.113 Uiso 1 1 calc R U . . .
C8 C 0.9229(6) 0.4081(5) 0.8704(3) 0.0633(9) Uani 1 1 d . . . . .
H8 H 0.951484 0.503677 0.871826 0.076 Uiso 1 1 calc R U . . .
C9 C 0.0027(6) 0.3424(5) 0.5590(4) 0.0733(11) Uani 1 1 d . . . . .
H9A H -0.008127 0.260319 0.605703 0.110 Uiso 1 1 calc R U . . .
H9B H -0.107218 0.339328 0.493815 0.110 Uiso 1 1 calc R U . . .
H9C H -0.018099 0.424302 0.604469 0.110 Uiso 1 1 calc R U . . .
C10 C 0.6721(6) 0.2172(5) 0.8288(3) 0.0646(9) Uani 1 1 d . . . . .
H10 H 0.532342 0.185200 0.804247 0.078 Uiso 1 1 calc R U . . .
C11 C 0.8376(8) 0.1225(5) 0.8633(4) 0.0748(11) Uani 1 1 d . . . . .
H11 H 0.809739 0.026840 0.860499 0.090 Uiso 1 1 calc R U . . .
C12 C 0.3657(6) 0.6408(4) 0.7966(3) 0.0591(8) Uani 1 1 d . . . . .
C13 C 1.0858(6) 0.3135(6) 0.9074(4) 0.0744(12) Uani 1 1 d . . . . .
H13 H 1.223441 0.345859 0.935913 0.089 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 C2 1.354(6) . ?
F2 C2 1.338(7) . ?
N1 C1 1.334(5) . ?
N1 C12 1.350(5) . ?
N2 H2 0.8600 . ?
N2 C1 1.336(4) . ?
N2 C4 1.480(4) . ?
N3 N4 1.381(4) . ?
N3 C12 1.313(5) . ?
N4 C1 1.367(4) . ?
N4 C6 1.418(5) . ?
C2 H2A 0.9800 . ?
C2 C12 1.487(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C4 1.514(6) . ?
C4 C7 1.505(6) . ?
C4 C9 1.525(5) . ?
C5 H5 0.9300 . ?
C5 C11 1.391(7) . ?
C5 C13 1.380(8) . ?
C6 C8 1.393(5) . ?
C6 C10 1.376(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C13 1.385(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C11 1.390(6) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 102.9(3) . . ?
C1 N2 H2 117.1 . . ?
C1 N2 C4 125.8(3) . . ?
C4 N2 H2 117.1 . . ?
C12 N3 N4 102.0(3) . . ?
N3 N4 C6 120.5(3) . . ?
C1 N4 N3 109.0(3) . . ?
C1 N4 C6 130.3(3) . . ?
N1 C1 N2 128.0(3) . . ?
N1 C1 N4 109.6(3) . . ?
N2 C1 N4 122.4(3) . . ?
F1 C2 H2A 110.5 . . ?
F1 C2 C12 110.3(4) . . ?
F2 C2 F1 103.6(4) . . ?
F2 C2 H2A 110.5 . . ?
F2 C2 C12 111.3(4) . . ?
C12 C2 H2A 110.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
N2 C4 C3 106.0(3) . . ?
N2 C4 C7 110.6(3) . . ?
N2 C4 C9 109.1(3) . . ?
C3 C4 C9 109.5(4) . . ?
C7 C4 C3 110.9(3) . . ?
C7 C4 C9 110.5(4) . . ?
C11 C5 H5 119.9 . . ?
C13 C5 H5 119.9 . . ?
C13 C5 C11 120.2(4) . . ?
C8 C6 N4 118.4(4) . . ?
C10 C6 N4 120.9(3) . . ?
C10 C6 C8 120.7(4) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8 120.3 . . ?
C13 C8 C6 119.3(4) . . ?
C13 C8 H8 120.3 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10 120.1 . . ?
C6 C10 C11 119.8(4) . . ?
C11 C10 H10 120.1 . . ?
C5 C11 H11 120.1 . . ?
C10 C11 C5 119.7(5) . . ?
C10 C11 H11 120.1 . . ?
N1 C12 C2 123.8(4) . . ?
N3 C12 N1 116.5(3) . . ?
N3 C12 C2 119.6(4) . . ?
C5 C13 C8 120.3(4) . . ?
C5 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?

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 C2 C12 N1 45.1(6) . . . . ?
F1 C2 C12 N3 -136.6(4) . . . . ?
F2 C2 C12 N1 -69.2(5) . . . . ?
F2 C2 C12 N3 109.0(5) . . . . ?
N3 N4 C1 N1 -1.0(4) . . . . ?
N3 N4 C1 N2 178.9(3) . . . . ?
N3 N4 C6 C8 -43.9(4) . . . . ?
N3 N4 C6 C10 135.2(4) . . . . ?
N4 N3 C12 N1 -0.6(5) . . . . ?
N4 N3 C12 C2 -179.0(3) . . . . ?
N4 C6 C8 C13 179.2(3) . . . . ?
N4 C6 C10 C11 179.3(3) . . . . ?
C1 N1 C12 N3 0.0(5) . . . . ?
C1 N1 C12 C2 178.3(4) . . . . ?
C1 N2 C4 C3 -174.7(4) . . . . ?
C1 N2 C4 C7 65.0(5) . . . . ?
C1 N2 C4 C9 -56.9(5) . . . . ?
C1 N4 C6 C8 132.0(4) . . . . ?
C1 N4 C6 C10 -48.9(5) . . . . ?
C4 N2 C1 N1 -7.8(6) . . . . ?
C4 N2 C1 N4 172.3(3) . . . . ?
C6 N4 C1 N1 -177.3(3) . . . . ?
C6 N4 C1 N2 2.6(6) . . . . ?
C6 C8 C13 C5 1.9(6) . . . . ?
C6 C10 C11 C5 1.3(6) . . . . ?
C8 C6 C10 C11 -1.6(6) . . . . ?
C10 C6 C8 C13 0.1(5) . . . . ?
C11 C5 C13 C8 -2.2(6) . . . . ?
C12 N1 C1 N2 -179.3(4) . . . . ?
C12 N1 C1 N4 0.6(4) . . . . ?
C12 N3 N4 C1 0.9(4) . . . . ?
C12 N3 N4 C6 177.6(3) . . . . ?
C13 C5 C11 C10 0.6(6) . . . . ?

_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 2.241
_oxdiff_exptl_absorpt_empirical_full_min 0.385
