# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_7587_2
_database_code_depnum_ccdc_archive 'CCDC 2285871'
loop_
_audit_author_name
_audit_author_address
'Shengxin sun'
;GuiZhou university
China
;
_audit_update_record             
;
2023-08-01 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_audit_creation_date             2023-07-29
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 F N3 O'
_chemical_formula_sum            'C18 H20 F N3 O'
_chemical_formula_weight         313.37
_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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.9658(5)
_cell_length_b                   11.9425(11)
_cell_length_c                   12.0846(7)
_cell_angle_alpha                99.941(6)
_cell_angle_beta                 91.228(5)
_cell_angle_gamma                102.361(7)
_cell_volume                     826.87(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2514
_cell_measurement_temperature    99.98(16)
_cell_measurement_theta_max      72.7570
_cell_measurement_theta_min      4.7830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7024
_diffrn_reflns_point_group_measured_fraction_full 0.602
_diffrn_reflns_point_group_measured_fraction_max 0.568
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.393
_diffrn_reflns_theta_min         3.720
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  28.00   0.50    0.51    --    0.00 -82.00 -90.00  102
  2  ω    -30.00  20.00   0.50    0.51    --    0.00 -82.00  60.00  100
  3  ω    -33.00  17.00   0.50    0.51    --    0.00 -82.00 150.00  100
  4  ω    -23.00  31.00   0.50    0.51    --    0.00 -82.00-180.00  108
  5  ω    -21.00   4.00   0.50    0.51    --    0.00 -82.00   0.00   50
  6  ω     77.00 121.00   0.50    0.60    --   95.20  45.00  60.00   88
  7  ω     57.00 111.00   0.50    0.60    --   95.20 -30.00 -90.00  108
  8  ω     15.00 127.00   0.50    0.60    --   95.20 -82.00-150.00  224
  9  ω     87.00 122.00   0.50    0.60    --   95.20 -82.00 -90.00   70
 10  ω      8.00  34.00   0.50    0.60    --   95.20 -82.00 -90.00   52
 11  ω      8.00  53.00   0.50    0.60    --   95.20 -30.00 -90.00   90
 12  ω     34.00 114.00   0.50    0.60    --   95.20 -82.00  90.00  160
 13  ω    131.00 180.00   0.50    0.60    --   95.20  45.00 -60.00   98
 14  ω    134.00 169.00   0.50    0.60    --   95.20  45.00  60.00   70
 15  ω      9.00 116.00   0.50    0.60    --   95.20 -61.00-150.00  214
 16  ω      8.00 103.00   0.50    0.60    --   95.20 -61.00  90.00  190
 17  ω     56.00  90.00   0.50    0.60    --   95.20 -77.00  30.00   68
 18  ω     87.00 126.00   0.50    0.60    --   95.20 -82.00 -60.00   78
 19  ω     94.00 177.00   0.50    0.60    --   95.20   0.00  90.00  166
 20  ω    142.00 182.00   0.50    0.60    --   95.20  82.00 120.00   80
 21  ω     12.00  81.00   0.50    0.60    --   95.20   0.00  90.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0390343000
_diffrn_orient_matrix_UB_12      -0.1338279000
_diffrn_orient_matrix_UB_13      -0.0187333000
_diffrn_orient_matrix_UB_21      -0.0453142000
_diffrn_orient_matrix_UB_22      -0.0063595000
_diffrn_orient_matrix_UB_23      -0.1271602000
_diffrn_orient_matrix_UB_31      0.2580055000
_diffrn_orient_matrix_UB_32      0.0091190000
_diffrn_orient_matrix_UB_33      -0.0170908000
_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         0.212
_reflns_Friedel_fraction_full    0.220
_reflns_Friedel_fraction_max     0.199
_reflns_number_gt                3268
_reflns_number_total             3818
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.030
_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)+(0.1353P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.1825
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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:
 C14(H14), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), N5(H5A),
 C19(H19), C20(H20), C21(H21), C32(H32), C33(H33), C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_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 0.3185(6) 0.8967(3) 1.2060(2) 0.0541(8) Uani 1 1 d . . . . .
O2 O 0.1557(6) 0.6110(3) 0.4038(3) 0.0394(8) Uani 1 1 d . . . . .
N1 N 0.1866(7) 0.6792(4) 0.7602(3) 0.0407(10) Uani 1 1 d . . . . .
H1 H 0.069472 0.692276 0.722763 0.049 Uiso 1 1 calc R U . . .
N2 N 0.4144(7) 0.5113(3) 0.5224(3) 0.0364(9) Uani 1 1 d . . . . .
N3 N -0.0072(7) 0.6869(4) 0.5575(3) 0.0362(9) Uani 1 1 d . . . . .
C1 C 0.2250(8) 0.7312(4) 0.8741(4) 0.0368(10) Uani 1 1 d . . . . .
C2 C 0.4390(8) 0.7997(5) 0.9171(4) 0.0405(11) Uani 1 1 d . . . . .
H2 H 0.563049 0.809252 0.869093 0.049 Uiso 1 1 calc R U . . .
C3 C 0.4730(9) 0.8542(4) 1.0293(4) 0.0403(11) Uani 1 1 d . . . . .
H3 H 0.619141 0.899990 1.058884 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2886(9) 0.8400(5) 1.0966(4) 0.0405(11) Uani 1 1 d . . . . .
C5 C 0.0757(9) 0.7723(5) 1.0572(4) 0.0433(12) Uani 1 1 d . . . . .
H5 H -0.048173 0.763974 1.105448 0.052 Uiso 1 1 calc R U . . .
C6 C 0.0460(9) 0.7168(5) 0.9461(4) 0.0395(11) Uani 1 1 d . . . . .
H6 H -0.098696 0.667940 0.918390 0.047 Uiso 1 1 calc R U . . .
C7 C 0.3162(8) 0.6095(4) 0.7021(4) 0.0373(10) Uani 1 1 d . . . . .
C8 C 0.4715(8) 0.5614(5) 0.7561(4) 0.0382(11) Uani 1 1 d . . . . .
H8 H 0.491208 0.576840 0.835925 0.046 Uiso 1 1 calc R U . . .
C9 C 0.5962(8) 0.4914(4) 0.6933(4) 0.0423(11) Uani 1 1 d . . . . .
H9 H 0.704282 0.459075 0.729050 0.051 Uiso 1 1 calc R U . . .
C10 C 0.5612(8) 0.4688(4) 0.5769(4) 0.0383(10) Uani 1 1 d . . . . .
H10 H 0.647545 0.420325 0.534243 0.046 Uiso 1 1 calc R U . . .
C11 C 0.2908(8) 0.5798(4) 0.5823(4) 0.0346(10) Uani 1 1 d . . . . .
C12 C 0.1381(8) 0.6281(4) 0.5174(4) 0.0355(10) Uani 1 1 d . . . . .
C13 C 0.0169(9) 0.6831(5) 0.3629(4) 0.0380(10) Uani 1 1 d . . . . .
H13A H -0.083473 0.639139 0.296320 0.046 Uiso 1 1 calc R U . . .
H13B H 0.115219 0.753515 0.342347 0.046 Uiso 1 1 calc R U . . .
C14 C -0.1263(8) 0.7159(4) 0.4622(4) 0.0344(10) Uani 1 1 d . . . . .
H14 H -0.282528 0.663057 0.448902 0.041 Uiso 1 1 calc R U . . .
C15 C -0.1552(8) 0.8430(4) 0.4836(4) 0.0378(10) Uani 1 1 d . . . . .
C16 C 0.0757(9) 0.9291(5) 0.5097(5) 0.0456(12) Uani 1 1 d . . . . .
H16A H 0.150249 0.916223 0.578033 0.068 Uiso 1 1 calc R U . . .
H16B H 0.051671 1.008861 0.521394 0.068 Uiso 1 1 calc R U . . .
H16C H 0.173736 0.917681 0.446591 0.068 Uiso 1 1 calc R U . . .
C17 C -0.2767(10) 0.8635(5) 0.3787(5) 0.0482(13) Uani 1 1 d . . . . .
H17A H -0.179021 0.855255 0.314931 0.072 Uiso 1 1 calc R U . . .
H17B H -0.305995 0.942267 0.392371 0.072 Uiso 1 1 calc R U . . .
H17C H -0.422902 0.806182 0.361507 0.072 Uiso 1 1 calc R U . . .
C18 C -0.3055(9) 0.8582(5) 0.5840(4) 0.0430(11) Uani 1 1 d . . . . .
H18A H -0.456013 0.804544 0.566284 0.064 Uiso 1 1 calc R U . . .
H18B H -0.325709 0.938602 0.599717 0.064 Uiso 1 1 calc R U . . .
H18C H -0.230959 0.841107 0.650275 0.064 Uiso 1 1 calc R U . . .
F3 F 0.6875(6) 0.1475(3) 0.5964(2) 0.0520(8) Uani 1 1 d . . . . .
O4 O 0.9012(6) 0.3978(3) -0.1202(3) 0.0449(9) Uani 1 1 d . . . . .
N4 N 0.6341(7) 0.5048(4) 0.0168(3) 0.0375(9) Uani 1 1 d . . . . .
N5 N 0.8269(7) 0.3371(4) 0.2114(3) 0.0413(10) Uani 1 1 d . . . . .
H5A H 0.941584 0.319313 0.172657 0.050 Uiso 1 1 calc R U . . .
N6 N 1.0274(7) 0.3159(4) 0.0164(3) 0.0358(9) Uani 1 1 d . . . . .
C19 C 0.4857(8) 0.5529(4) 0.0795(4) 0.0407(11) Uani 1 1 d . . . . .
H19 H 0.409720 0.604262 0.049538 0.049 Uiso 1 1 calc R U . . .
C20 C 0.4379(9) 0.5310(5) 0.1863(4) 0.0415(11) Uani 1 1 d . . . . .
H20 H 0.329141 0.565986 0.227578 0.050 Uiso 1 1 calc R U . . .
C21 C 0.5472(8) 0.4590(5) 0.2323(4) 0.0407(11) Uani 1 1 d . . . . .
H21 H 0.516187 0.444402 0.305899 0.049 Uiso 1 1 calc R U . . .
C22 C 0.7069(8) 0.4062(4) 0.1697(4) 0.0347(10) Uani 1 1 d . . . . .
C23 C 0.7427(8) 0.4332(4) 0.0605(4) 0.0344(10) Uani 1 1 d . . . . .
C24 C 0.8974(8) 0.3795(4) -0.0128(4) 0.0348(10) Uani 1 1 d . . . . .
C25 C 1.0366(9) 0.3212(5) -0.1786(4) 0.0416(11) Uani 1 1 d . . . . .
H25A H 1.150824 0.363363 -0.223739 0.050 Uiso 1 1 calc R U . . .
H25B H 0.937009 0.253756 -0.228762 0.050 Uiso 1 1 calc R U . . .
C26 C 1.1563(8) 0.2814(5) -0.0825(4) 0.0395(11) Uani 1 1 d . . . . .
H26 H 1.316592 0.330038 -0.069479 0.047 Uiso 1 1 calc R U . . .
C27 C 1.1719(8) 0.1531(4) -0.1009(4) 0.0399(11) Uani 1 1 d . . . . .
C28 C 1.3000(10) 0.1329(5) 0.0022(5) 0.0505(13) Uani 1 1 d . . . . .
H28A H 1.452745 0.185140 0.013042 0.076 Uiso 1 1 calc R U . . .
H28B H 1.315925 0.051784 -0.009315 0.076 Uiso 1 1 calc R U . . .
H28C H 1.213334 0.148812 0.068904 0.076 Uiso 1 1 calc R U . . .
C29 C 1.3102(10) 0.1296(6) -0.2042(5) 0.0544(14) Uani 1 1 d . . . . .
H29A H 1.238635 0.151088 -0.268825 0.082 Uiso 1 1 calc R U . . .
H29B H 1.312825 0.046677 -0.220886 0.082 Uiso 1 1 calc R U . . .
H29C H 1.467881 0.176125 -0.188911 0.082 Uiso 1 1 calc R U . . .
C30 C 0.9340(10) 0.0717(5) -0.1171(6) 0.0531(14) Uani 1 1 d . . . . .
H30A H 0.847592 0.088251 -0.050377 0.080 Uiso 1 1 calc R U . . .
H30B H 0.950065 -0.009406 -0.127730 0.080 Uiso 1 1 calc R U . . .
H30C H 0.851500 0.083847 -0.183417 0.080 Uiso 1 1 calc R U . . .
C31 C 0.7867(9) 0.2906(4) 0.3110(4) 0.0387(11) Uani 1 1 d . . . . .
C32 C 0.9685(9) 0.3066(5) 0.3911(4) 0.0395(11) Uani 1 1 d . . . . .
H32 H 1.115173 0.351792 0.380111 0.047 Uiso 1 1 calc R U . . .
C33 C 0.9360(9) 0.2570(5) 0.4861(4) 0.0420(11) Uani 1 1 d . . . . .
H33 H 1.060147 0.265792 0.539770 0.050 Uiso 1 1 calc R U . . .
C34 C 0.7213(10) 0.1949(4) 0.5018(4) 0.0423(12) Uani 1 1 d . . . . .
C35 C 0.5395(10) 0.1775(5) 0.4246(4) 0.0435(12) Uani 1 1 d . . . . .
H35 H 0.393107 0.132829 0.436901 0.052 Uiso 1 1 calc R U . . .
C36 C 0.5724(9) 0.2257(4) 0.3288(4) 0.0412(11) Uani 1 1 d . . . . .
H36 H 0.447943 0.214361 0.274764 0.049 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 C4 1.367(6) . ?
O2 C12 1.363(5) . ?
O2 C13 1.451(5) . ?
N1 H1 0.8800 . ?
N1 C1 1.402(6) . ?
N1 C7 1.371(6) . ?
N2 C10 1.318(6) . ?
N2 C11 1.347(6) . ?
N3 C12 1.280(6) . ?
N3 C14 1.469(6) . ?
C1 C2 1.395(7) . ?
C1 C6 1.393(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(7) . ?
C4 C5 1.377(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(6) . ?
C7 C11 1.427(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.459(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.533(6) . ?
C14 H14 1.0000 . ?
C14 C15 1.543(7) . ?
C15 C16 1.522(7) . ?
C15 C17 1.528(7) . ?
C15 C18 1.533(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
F3 C34 1.362(5) . ?
O4 C24 1.352(5) . ?
O4 C25 1.452(6) . ?
N4 C19 1.335(6) . ?
N4 C23 1.345(6) . ?
N5 H5A 0.8800 . ?
N5 C22 1.352(6) . ?
N5 C31 1.415(6) . ?
N6 C24 1.279(6) . ?
N6 C26 1.481(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.364(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.415(6) . ?
C22 C23 1.422(6) . ?
C23 C24 1.463(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.544(6) . ?
C26 H26 1.0000 . ?
C26 C27 1.533(7) . ?
C27 C28 1.528(7) . ?
C27 C29 1.529(7) . ?
C27 C30 1.527(7) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.397(7) . ?
C31 C36 1.388(7) . ?
C32 H32 0.9500 . ?
C32 C33 1.378(7) . ?
C33 H33 0.9500 . ?
C33 C34 1.371(8) . ?
C34 C35 1.372(8) . ?
C35 H35 0.9500 . ?
C35 C36 1.378(7) . ?
C36 H36 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
C12 O2 C13 105.3(4) . . ?
C1 N1 H1 117.3 . . ?
C7 N1 H1 117.3 . . ?
C7 N1 C1 125.4(4) . . ?
C10 N2 C11 118.6(4) . . ?
C12 N3 C14 107.6(4) . . ?
C2 C1 N1 121.3(4) . . ?
C6 C1 N1 119.8(5) . . ?
C6 C1 C2 118.8(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.2(5) . . ?
C4 C3 H3 120.9 . . ?
F1 C4 C3 118.5(5) . . ?
F1 C4 C5 118.9(4) . . ?
C5 C4 C3 122.5(5) . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.6(5) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(5) . . ?
C5 C6 H6 119.5 . . ?
N1 C7 C8 122.4(4) . . ?
N1 C7 C11 120.6(4) . . ?
C8 C7 C11 117.0(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(4) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
N2 C10 C9 123.4(4) . . ?
N2 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
N2 C11 C7 122.3(4) . . ?
N2 C11 C12 116.2(4) . . ?
C7 C11 C12 121.4(4) . . ?
O2 C12 C11 116.7(4) . . ?
N3 C12 O2 117.2(4) . . ?
N3 C12 C11 126.1(4) . . ?
O2 C13 H13A 110.9 . . ?
O2 C13 H13B 110.9 . . ?
O2 C13 C14 104.2(3) . . ?
H13A C13 H13B 108.9 . . ?
C14 C13 H13A 110.9 . . ?
C14 C13 H13B 110.9 . . ?
N3 C14 C13 103.2(3) . . ?
N3 C14 H14 108.3 . . ?
N3 C14 C15 112.9(4) . . ?
C13 C14 H14 108.3 . . ?
C13 C14 C15 115.6(4) . . ?
C15 C14 H14 108.3 . . ?
C16 C15 C14 111.5(4) . . ?
C16 C15 C17 110.3(4) . . ?
C16 C15 C18 109.4(4) . . ?
C17 C15 C14 108.2(4) . . ?
C17 C15 C18 109.6(4) . . ?
C18 C15 C14 107.8(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 O4 C25 106.1(4) . . ?
C19 N4 C23 118.1(4) . . ?
C22 N5 H5A 116.7 . . ?
C22 N5 C31 126.6(4) . . ?
C31 N5 H5A 116.7 . . ?
C24 N6 C26 107.3(4) . . ?
N4 C19 H19 118.6 . . ?
N4 C19 C20 122.8(4) . . ?
C20 C19 H19 118.6 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.9(5) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.6(4) . . ?
C22 C21 H21 120.2 . . ?
N5 C22 C21 122.7(4) . . ?
N5 C22 C23 121.0(4) . . ?
C21 C22 C23 116.3(4) . . ?
N4 C23 C22 123.3(4) . . ?
N4 C23 C24 116.1(4) . . ?
C22 C23 C24 120.6(4) . . ?
O4 C24 C23 117.2(4) . . ?
N6 C24 O4 117.6(4) . . ?
N6 C24 C23 125.2(4) . . ?
O4 C25 H25A 111.0 . . ?
O4 C25 H25B 111.0 . . ?
O4 C25 C26 103.7(4) . . ?
H25A C25 H25B 109.0 . . ?
C26 C25 H25A 111.0 . . ?
C26 C25 H25B 111.0 . . ?
N6 C26 C25 103.1(3) . . ?
N6 C26 H26 107.7 . . ?
N6 C26 C27 113.4(4) . . ?
C25 C26 H26 107.7 . . ?
C27 C26 C25 116.8(4) . . ?
C27 C26 H26 107.7 . . ?
C28 C27 C26 108.4(4) . . ?
C28 C27 C29 109.0(4) . . ?
C29 C27 C26 108.0(4) . . ?
C30 C27 C26 111.6(4) . . ?
C30 C27 C28 109.1(4) . . ?
C30 C27 C29 110.6(5) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 N5 119.4(4) . . ?
C36 C31 N5 121.3(4) . . ?
C36 C31 C32 119.3(4) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.3(5) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 120.6 . . ?
C34 C33 C32 118.8(5) . . ?
C34 C33 H33 120.6 . . ?
F3 C34 C33 119.0(5) . . ?
F3 C34 C35 118.8(5) . . ?
C33 C34 C35 122.3(4) . . ?
C34 C35 H35 120.5 . . ?
C34 C35 C36 119.0(5) . . ?
C36 C35 H35 120.5 . . ?
C31 C36 H36 119.8 . . ?
C35 C36 C31 120.3(5) . . ?
C35 C36 H36 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
F1 C4 C5 C6 179.0(4) . . . . ?
O2 C13 C14 N3 15.4(5) . . . . ?
O2 C13 C14 C15 139.1(4) . . . . ?
N1 C1 C2 C3 177.8(4) . . . . ?
N1 C1 C6 C5 -176.4(4) . . . . ?
N1 C7 C8 C9 179.6(5) . . . . ?
N1 C7 C11 N2 -179.8(5) . . . . ?
N1 C7 C11 C12 4.0(7) . . . . ?
N2 C11 C12 O2 -7.6(6) . . . . ?
N2 C11 C12 N3 173.8(5) . . . . ?
N3 C14 C15 C16 57.6(5) . . . . ?
N3 C14 C15 C17 179.0(4) . . . . ?
N3 C14 C15 C18 -62.5(5) . . . . ?
C1 N1 C7 C8 14.6(8) . . . . ?
C1 N1 C7 C11 -167.6(5) . . . . ?
C1 C2 C3 C4 -0.8(7) . . . . ?
C2 C1 C6 C5 2.4(7) . . . . ?
C2 C3 C4 F1 -177.7(4) . . . . ?
C2 C3 C4 C5 1.4(7) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C4 C5 C6 C1 -1.9(7) . . . . ?
C6 C1 C2 C3 -1.0(7) . . . . ?
C7 N1 C1 C2 53.4(7) . . . . ?
C7 N1 C1 C6 -127.9(5) . . . . ?
C7 C8 C9 C10 -1.0(8) . . . . ?
C7 C11 C12 O2 168.9(4) . . . . ?
C7 C11 C12 N3 -9.7(7) . . . . ?
C8 C7 C11 N2 -1.8(7) . . . . ?
C8 C7 C11 C12 -178.1(4) . . . . ?
C8 C9 C10 N2 0.2(8) . . . . ?
C10 N2 C11 C7 1.1(7) . . . . ?
C10 N2 C11 C12 177.6(4) . . . . ?
C11 N2 C10 C9 -0.2(7) . . . . ?
C11 C7 C8 C9 1.7(7) . . . . ?
C12 O2 C13 C14 -14.2(5) . . . . ?
C12 N3 C14 C13 -11.3(5) . . . . ?
C12 N3 C14 C15 -136.8(4) . . . . ?
C13 O2 C12 N3 8.0(6) . . . . ?
C13 O2 C12 C11 -170.6(4) . . . . ?
C13 C14 C15 C16 -60.8(5) . . . . ?
C13 C14 C15 C17 60.6(5) . . . . ?
C13 C14 C15 C18 179.0(4) . . . . ?
C14 N3 C12 O2 2.5(6) . . . . ?
C14 N3 C12 C11 -178.9(4) . . . . ?
F3 C34 C35 C36 179.7(4) . . . . ?
O4 C25 C26 N6 14.2(5) . . . . ?
O4 C25 C26 C27 139.4(4) . . . . ?
N4 C19 C20 C21 1.1(8) . . . . ?
N4 C23 C24 O4 -5.9(7) . . . . ?
N4 C23 C24 N6 174.7(5) . . . . ?
N5 C22 C23 N4 -177.5(5) . . . . ?
N5 C22 C23 C24 4.8(7) . . . . ?
N5 C31 C32 C33 -176.7(5) . . . . ?
N5 C31 C36 C35 177.5(5) . . . . ?
N6 C26 C27 C28 -61.5(5) . . . . ?
N6 C26 C27 C29 -179.5(4) . . . . ?
N6 C26 C27 C30 58.7(6) . . . . ?
C19 N4 C23 C22 0.1(7) . . . . ?
C19 N4 C23 C24 177.9(4) . . . . ?
C19 C20 C21 C22 -0.7(8) . . . . ?
C20 C21 C22 N5 177.7(5) . . . . ?
C20 C21 C22 C23 0.1(7) . . . . ?
C21 C22 C23 N4 0.2(7) . . . . ?
C21 C22 C23 C24 -177.6(4) . . . . ?
C22 N5 C31 C32 -127.9(5) . . . . ?
C22 N5 C31 C36 54.6(7) . . . . ?
C22 C23 C24 O4 172.0(5) . . . . ?
C22 C23 C24 N6 -7.4(7) . . . . ?
C23 N4 C19 C20 -0.7(7) . . . . ?
C24 O4 C25 C26 -13.7(5) . . . . ?
C24 N6 C26 C25 -10.0(5) . . . . ?
C24 N6 C26 C27 -137.3(4) . . . . ?
C25 O4 C24 N6 8.4(6) . . . . ?
C25 O4 C24 C23 -170.9(4) . . . . ?
C25 C26 C27 C28 178.8(4) . . . . ?
C25 C26 C27 C29 60.8(5) . . . . ?
C25 C26 C27 C30 -61.0(6) . . . . ?
C26 N6 C24 O4 1.5(6) . . . . ?
C26 N6 C24 C23 -179.2(5) . . . . ?
C31 N5 C22 C21 11.9(8) . . . . ?
C31 N5 C22 C23 -170.7(5) . . . . ?
C31 C32 C33 C34 -1.8(7) . . . . ?
C32 C31 C36 C35 0.0(7) . . . . ?
C32 C33 C34 F3 -178.9(5) . . . . ?
C32 C33 C34 C35 2.0(8) . . . . ?
C33 C34 C35 C36 -1.1(8) . . . . ?
C34 C35 C36 C31 0.1(8) . . . . ?
C36 C31 C32 C33 0.8(7) . . . . ?

_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 1.743
_oxdiff_exptl_absorpt_empirical_full_min 0.489
