# 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_a-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2178596'
loop_
_audit_author_name
_audit_author_address
'li xiao yong'
;NWNU
China
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_audit_creation_date             2022-06-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 F2 N4 O'
_chemical_formula_sum            'C25 H20 F2 N4 O'
_chemical_formula_weight         430.45
_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                   8.9855(2)
_cell_length_b                   19.7009(3)
_cell_length_c                   12.8893(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.475(2)
_cell_angle_gamma                90
_cell_volume                     2227.82(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8057
_cell_measurement_temperature    301.78(10)
_cell_measurement_theta_max      75.9680
_cell_measurement_theta_min      4.1750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87963
_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    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15574
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.512
_diffrn_reflns_theta_min         4.168
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.78(10)
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    102.00 128.00   0.50    0.25    --  107.75  24.00-152.00   52
  2  ω    150.00 175.00   0.50    0.25    --  107.75  19.00 -30.00   50
  3  ω    116.00 142.00   0.50    0.25    --  107.75  19.00 -30.00   52
  4  ω     45.00 100.00   0.50    0.08    --   47.57  24.00-152.00  110
  5  ω   -109.00 -81.00   0.50    0.25    -- -100.00  77.00  30.00   56
  6  ω    -75.00 -31.00   0.50    0.25    -- -100.00  77.00  30.00   88
  7  ω    -69.00 -39.00   0.50    0.25    -- -100.00  57.00   0.00   60
  8  ω    -69.00 -27.00   0.50    0.25    -- -100.00  57.00  30.00   84
  9  ω    -66.00 -36.00   0.50    0.25    -- -100.00  57.00 -30.00   60
 10  ω    -69.00 -33.00   0.50    0.25    -- -100.00  57.00  90.00   72
 11  ω    -54.00 -27.00   0.50    0.25    -- -100.00  57.00 -60.00   54
 12  ω    -68.00 -28.00   0.50    0.25    -- -100.00  77.00-180.00   80
 13  ω    -69.00 -34.00   0.50    0.25    -- -100.00  57.00-180.00   70
 14  ω   -108.00 -79.00   0.50    0.25    -- -100.00  77.00-180.00   58
 15  ω    -69.00 -27.00   0.50    0.25    -- -100.00  57.00 120.00   84
 16  ω    -69.00 -33.00   0.50    0.25    -- -100.00  57.00 150.00   72
 17  ω   -174.00 -87.00   0.50    0.25    -- -100.00 -24.00  42.00  174
 18  ω   -122.00 -40.00   0.50    0.08    --  -47.57 -24.00  42.00  164
 19  ω    -93.00 -64.00   0.50    0.08    --  -47.57 125.00 -30.00   58
 20  ω    -50.00 -23.00   0.50    0.08    --  -47.57 125.00 -30.00   54
 21  ω     43.00 109.00   0.50    0.25    --  107.75-125.00 -60.00  132
 22  ω     35.00  60.00   0.50    0.25    --  107.75 -57.00-150.00   50
 23  ω     59.00  85.00   0.50    0.25    --  107.75 -99.00 -60.00   52
 24  ω     36.00  61.00   0.50    0.25    --  107.75 -57.00 120.00   50
 25  ω     -3.00  27.00   0.50    0.08    --   47.57 -24.00  42.00   60
 26  ω    -27.00  23.00   0.50    0.08    --   47.57 -19.00 -90.00  100
 27  ω    -25.00   0.00   0.50    0.08    --  -47.57  24.00-152.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1691356000
_diffrn_orient_matrix_UB_12      -0.0145805000
_diffrn_orient_matrix_UB_13      -0.0484650000
_diffrn_orient_matrix_UB_21      0.0232221000
_diffrn_orient_matrix_UB_22      0.0231219000
_diffrn_orient_matrix_UB_23      -0.1096073000
_diffrn_orient_matrix_UB_31      0.0408834000
_diffrn_orient_matrix_UB_32      -0.0732695000
_diffrn_orient_matrix_UB_33      -0.0249864000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3589
_reflns_number_total             4439
_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         0.501
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4439
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0621
_refine_ls_restrained_S_all      1.249
_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)+(0.1077P)²+0.4269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1853
_refine_ls_wR_factor_ref         0.1944
_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. Restrained distances
 C22-F1B \\sim C22-F1
 with sigma of 0.02
 C22-F2 \\sim C22-F2B
 with sigma of 0.02
 F1B-F2 \\sim F1B-F2B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F1B) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2B)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.005
4. Others
 Fixed Sof: F1(0.5) F1B(0.5) F2(0.5) F2B(0.5) H22A(0.5) H22(0.5)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C22(H22A), C22(H22)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 0.7962(7) 0.1574(5) 0.6948(5) 0.190(2) Uani 0.5 1 d D U P A 1
F1B F 0.8383(6) 0.2140(3) 0.6932(4) 0.1316(15) Uani 0.5 1 d D U P A 2
F2 F 0.9029(6) 0.2235(3) 0.6149(7) 0.1558(19) Uani 0.5 1 d D U P A 1
F2B F 0.9038(4) 0.1985(3) 0.5367(5) 0.1357(15) Uani 0.5 1 d D U P A 2
O1 O 0.50819(16) 0.26862(7) 0.29293(11) 0.0651(4) Uani 1 1 d . . . . .
N1 N 0.32630(18) 0.33916(8) 0.33853(12) 0.0585(4) Uani 1 1 d . . . . .
N2 N 0.41773(18) 0.18122(8) 0.45569(13) 0.0621(4) Uani 1 1 d . . . . .
N3 N 0.23811(19) 0.34019(9) 0.41753(13) 0.0642(4) Uani 1 1 d . . . . .
N4 N 0.5621(2) 0.15575(9) 0.49309(16) 0.0709(5) Uani 1 1 d . . . . .
C1 C 0.4288(2) 0.28709(9) 0.35257(14) 0.0534(4) Uani 1 1 d . . . . .
C2 C 0.5677(2) 0.26925(10) 0.54745(15) 0.0603(5) Uani 1 1 d . . . . .
H2 H 0.536768 0.270173 0.615855 0.072 Uiso 1 1 calc R U . . .
C3 C 0.2853(2) 0.29229(10) 0.48367(15) 0.0600(5) Uani 1 1 d . . . . .
C4 C 0.2916(2) 0.38616(9) 0.25344(14) 0.0606(5) Uani 1 1 d . . . . .
C5 C 0.4201(2) 0.25586(9) 0.45976(14) 0.0548(4) Uani 1 1 d . . . . .
C6 C 0.3208(2) 0.14405(10) 0.37458(16) 0.0632(5) Uani 1 1 d . . . . .
C7 C 0.6455(2) 0.33589(10) 0.53692(15) 0.0610(5) Uani 1 1 d . . . . .
C8 C 0.6474(2) 0.20264(11) 0.54157(18) 0.0697(5) Uani 1 1 d . . . . .
C9 C 0.4020(3) 0.40267(11) 0.19800(18) 0.0766(6) Uani 1 1 d . . . . .
H9 H 0.498471 0.383263 0.216046 0.092 Uiso 1 1 calc R U . . .
C10 C 0.1682(3) 0.16052(12) 0.3449(2) 0.0778(6) Uani 1 1 d . . . . .
H10 H 0.130009 0.197449 0.375800 0.093 Uiso 1 1 calc R U . . .
C11 C 0.7482(3) 0.34430(12) 0.47209(18) 0.0743(6) Uani 1 1 d . . . . .
H11 H 0.775132 0.307414 0.435043 0.089 Uiso 1 1 calc R U . . .
C12 C 0.1494(3) 0.41575(12) 0.2284(2) 0.0799(6) Uani 1 1 d . . . . .
H12 H 0.075377 0.404364 0.265891 0.096 Uiso 1 1 calc R U . . .
C13 C 0.3760(3) 0.08963(13) 0.3264(2) 0.0841(7) Uani 1 1 d . . . . .
H13 H 0.479178 0.078926 0.343947 0.101 Uiso 1 1 calc R U . . .
C14 C 0.3663(4) 0.44884(12) 0.1147(2) 0.0921(8) Uani 1 1 d . . . . .
H14 H 0.438571 0.459308 0.075242 0.111 Uiso 1 1 calc R U . . .
C15 C 0.2173(3) 0.27903(15) 0.5768(2) 0.0838(7) Uani 1 1 d . . . . .
H15A H 0.284466 0.295569 0.639956 0.126 Uiso 1 1 calc R U . . .
H15B H 0.202495 0.231085 0.583279 0.126 Uiso 1 1 calc R U . . .
H15C H 0.120890 0.301835 0.567321 0.126 Uiso 1 1 calc R U . . .
C16 C 0.6085(3) 0.39169(14) 0.5909(2) 0.0867(7) Uani 1 1 d . . . . .
H16 H 0.540918 0.386744 0.635839 0.104 Uiso 1 1 calc R U . . .
C17 C 0.0719(3) 0.12188(15) 0.2688(2) 0.0930(8) Uani 1 1 d . . . . .
H17 H -0.030683 0.133308 0.248107 0.112 Uiso 1 1 calc R U . . .
C18 C 0.2275(5) 0.47867(15) 0.0905(2) 0.1062(10) Uani 1 1 d . . . . .
H18 H 0.205674 0.510185 0.035613 0.127 Uiso 1 1 calc R U . . .
C19 C 0.1185(4) 0.46261(15) 0.1468(3) 0.1036(9) Uani 1 1 d . . . . .
H19 H 0.023372 0.483406 0.129809 0.124 Uiso 1 1 calc R U . . .
C20 C 0.7702(4) 0.46259(15) 0.5155(3) 0.1102(11) Uani 1 1 d . . . . .
H20 H 0.811059 0.505202 0.507907 0.132 Uiso 1 1 calc R U . . .
C21 C 0.8111(3) 0.40761(16) 0.4622(2) 0.0969(8) Uani 1 1 d . . . . .
H21 H 0.881200 0.412914 0.419214 0.116 Uiso 1 1 calc R U . . .
C22 C 0.8035(3) 0.18263(17) 0.6005(3) 0.1021(9) Uani 1 1 d D . . . .
H22A H 0.805707 0.133501 0.612657 0.123 Uiso 0.5 1 calc R U P A 2
H22 H 0.836540 0.145456 0.560265 0.123 Uiso 0.5 1 calc R U P A 1
C23 C 0.1272(4) 0.06687(16) 0.2238(3) 0.1036(9) Uani 1 1 d . . . . .
H23 H 0.062033 0.040332 0.174105 0.124 Uiso 1 1 calc R U . . .
C24 C 0.6696(4) 0.45423(15) 0.5796(3) 0.1095(10) Uani 1 1 d . . . . .
H24 H 0.641972 0.491293 0.615938 0.131 Uiso 1 1 calc R U . . .
C25 C 0.2778(4) 0.05142(16) 0.2523(3) 0.1079(10) Uani 1 1 d . . . . .
H25 H 0.315182 0.014336 0.221281 0.130 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 C22 1.327(6) . ?
F1B C22 1.321(6) . ?
F2 C22 1.187(5) . ?
F2B C22 1.380(6) . ?
O1 C1 1.212(2) . ?
N1 N3 1.419(2) . ?
N1 C1 1.364(2) . ?
N1 C4 1.418(2) . ?
N2 N4 1.377(2) . ?
N2 C5 1.471(2) . ?
N2 C6 1.412(3) . ?
N3 C3 1.281(3) . ?
N4 C8 1.274(3) . ?
C1 C5 1.530(2) . ?
C2 H2 0.9800 . ?
C2 C5 1.568(3) . ?
C2 C7 1.507(3) . ?
C2 C8 1.505(3) . ?
C3 C5 1.496(3) . ?
C3 C15 1.483(3) . ?
C4 C9 1.381(3) . ?
C4 C12 1.378(3) . ?
C6 C10 1.380(3) . ?
C6 C13 1.384(3) . ?
C7 C11 1.382(3) . ?
C7 C16 1.380(3) . ?
C8 C22 1.497(3) . ?
C9 H9 0.9300 . ?
C9 C14 1.391(3) . ?
C10 H10 0.9300 . ?
C10 C17 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C21 1.387(3) . ?
C12 H12 0.9300 . ?
C12 C19 1.382(4) . ?
C13 H13 0.9300 . ?
C13 C25 1.375(4) . ?
C14 H14 0.9300 . ?
C14 C18 1.353(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C24 1.370(4) . ?
C17 H17 0.9300 . ?
C17 C23 1.372(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.375(5) . ?
C20 C24 1.359(5) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9800 . ?
C22 H22 0.9800 . ?
C23 H23 0.9300 . ?
C23 C25 1.358(5) . ?
C24 H24 0.9300 . ?
C25 H25 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 N3 112.41(14) . . ?
C1 N1 C4 128.54(16) . . ?
C4 N1 N3 118.82(15) . . ?
N4 N2 C5 110.26(14) . . ?
N4 N2 C6 117.00(17) . . ?
C6 N2 C5 123.13(15) . . ?
C3 N3 N1 108.12(15) . . ?
C8 N4 N2 109.19(17) . . ?
O1 C1 N1 127.93(17) . . ?
O1 C1 C5 127.14(16) . . ?
N1 C1 C5 104.93(14) . . ?
C5 C2 H2 107.0 . . ?
C7 C2 H2 107.0 . . ?
C7 C2 C5 114.72(16) . . ?
C8 C2 H2 107.0 . . ?
C8 C2 C5 98.89(16) . . ?
C8 C2 C7 121.32(17) . . ?
N3 C3 C5 112.50(16) . . ?
N3 C3 C15 122.23(19) . . ?
C15 C3 C5 125.15(19) . . ?
C9 C4 N1 119.45(19) . . ?
C12 C4 N1 119.7(2) . . ?
C12 C4 C9 120.8(2) . . ?
N2 C5 C1 111.90(15) . . ?
N2 C5 C2 101.39(14) . . ?
N2 C5 C3 118.72(15) . . ?
C1 C5 C2 112.54(14) . . ?
C3 C5 C1 101.22(15) . . ?
C3 C5 C2 111.53(15) . . ?
C10 C6 N2 120.0(2) . . ?
C10 C6 C13 119.2(2) . . ?
C13 C6 N2 120.7(2) . . ?
C11 C7 C2 122.83(19) . . ?
C16 C7 C2 118.8(2) . . ?
C16 C7 C11 118.3(2) . . ?
N4 C8 C2 114.48(18) . . ?
N4 C8 C22 117.2(2) . . ?
C22 C8 C2 127.5(2) . . ?
C4 C9 H9 120.6 . . ?
C4 C9 C14 118.8(3) . . ?
C14 C9 H9 120.6 . . ?
C6 C10 H10 120.1 . . ?
C6 C10 C17 119.9(2) . . ?
C17 C10 H10 120.1 . . ?
C7 C11 H11 119.9 . . ?
C7 C11 C21 120.2(2) . . ?
C21 C11 H11 119.9 . . ?
C4 C12 H12 120.5 . . ?
C4 C12 C19 119.0(3) . . ?
C19 C12 H12 120.5 . . ?
C6 C13 H13 120.1 . . ?
C25 C13 C6 119.8(3) . . ?
C25 C13 H13 120.1 . . ?
C9 C14 H14 119.7 . . ?
C18 C14 C9 120.6(3) . . ?
C18 C14 H14 119.7 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C16 H16 119.4 . . ?
C24 C16 C7 121.1(3) . . ?
C24 C16 H16 119.4 . . ?
C10 C17 H17 119.8 . . ?
C23 C17 C10 120.3(3) . . ?
C23 C17 H17 119.8 . . ?
C14 C18 H18 119.8 . . ?
C14 C18 C19 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C12 C19 H19 119.8 . . ?
C18 C19 C12 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C21 C20 H20 120.2 . . ?
C24 C20 H20 120.2 . . ?
C24 C20 C21 119.5(3) . . ?
C11 C21 H21 119.9 . . ?
C20 C21 C11 120.3(3) . . ?
C20 C21 H21 119.9 . . ?
F1 C22 C8 109.7(4) . . ?
F1 C22 H22 106.6 . . ?
F1B C22 F2B 112.0(4) . . ?
F1B C22 C8 110.4(3) . . ?
F1B C22 H22A 109.0 . . ?
F2 C22 F1 107.2(6) . . ?
F2 C22 C8 119.5(4) . . ?
F2 C22 H22 106.6 . . ?
F2B C22 C8 107.4(3) . . ?
F2B C22 H22A 109.0 . . ?
C8 C22 H22A 109.0 . . ?
C8 C22 H22 106.6 . . ?
C17 C23 H23 120.2 . . ?
C25 C23 C17 119.6(3) . . ?
C25 C23 H23 120.2 . . ?
C16 C24 H24 119.7 . . ?
C20 C24 C16 120.6(3) . . ?
C20 C24 H24 119.7 . . ?
C13 C25 H25 119.4 . . ?
C23 C25 C13 121.2(3) . . ?
C23 C25 H25 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C5 N2 -42.9(2) . . . . ?
O1 C1 C5 C2 70.5(2) . . . . ?
O1 C1 C5 C3 -170.32(18) . . . . ?
N1 N3 C3 C5 3.8(2) . . . . ?
N1 N3 C3 C15 -179.99(19) . . . . ?
N1 C1 C5 N2 136.14(15) . . . . ?
N1 C1 C5 C2 -110.46(17) . . . . ?
N1 C1 C5 C3 8.71(18) . . . . ?
N1 C4 C9 C14 179.99(19) . . . . ?
N1 C4 C12 C19 178.6(2) . . . . ?
N2 N4 C8 C2 2.1(3) . . . . ?
N2 N4 C8 C22 172.1(2) . . . . ?
N2 C6 C10 C17 -176.9(2) . . . . ?
N2 C6 C13 C25 175.9(2) . . . . ?
N3 N1 C1 O1 171.60(18) . . . . ?
N3 N1 C1 C5 -7.43(19) . . . . ?
N3 N1 C4 C9 157.70(18) . . . . ?
N3 N1 C4 C12 -21.0(3) . . . . ?
N3 C3 C5 N2 -130.71(18) . . . . ?
N3 C3 C5 C1 -7.9(2) . . . . ?
N3 C3 C5 C2 112.02(19) . . . . ?
N4 N2 C5 C1 96.97(18) . . . . ?
N4 N2 C5 C2 -23.19(19) . . . . ?
N4 N2 C5 C3 -145.69(17) . . . . ?
N4 N2 C6 C10 170.01(19) . . . . ?
N4 N2 C6 C13 -8.0(3) . . . . ?
N4 C8 C22 F1 -81.8(5) . . . . ?
N4 C8 C22 F1B -138.4(4) . . . . ?
N4 C8 C22 F2 154.0(7) . . . . ?
N4 C8 C22 F2B 99.2(4) . . . . ?
C1 N1 N3 C3 2.6(2) . . . . ?
C1 N1 C4 C9 -28.2(3) . . . . ?
C1 N1 C4 C12 153.1(2) . . . . ?
C2 C7 C11 C21 177.2(2) . . . . ?
C2 C7 C16 C24 -176.4(2) . . . . ?
C2 C8 C22 F1 86.7(5) . . . . ?
C2 C8 C22 F1B 30.1(5) . . . . ?
C2 C8 C22 F2 -37.5(8) . . . . ?
C2 C8 C22 F2B -92.3(4) . . . . ?
C4 N1 N3 C3 177.64(17) . . . . ?
C4 N1 C1 O1 -2.8(3) . . . . ?
C4 N1 C1 C5 178.13(17) . . . . ?
C4 C9 C14 C18 2.1(4) . . . . ?
C4 C12 C19 C18 0.9(4) . . . . ?
C5 N2 N4 C8 14.4(2) . . . . ?
C5 N2 C6 C10 -47.2(3) . . . . ?
C5 N2 C6 C13 134.8(2) . . . . ?
C5 C2 C7 C11 -84.6(2) . . . . ?
C5 C2 C7 C16 92.7(2) . . . . ?
C5 C2 C8 N4 -15.9(2) . . . . ?
C5 C2 C8 C22 175.4(2) . . . . ?
C6 N2 N4 C8 161.71(18) . . . . ?
C6 N2 C5 C1 -48.0(2) . . . . ?
C6 N2 C5 C2 -168.14(17) . . . . ?
C6 N2 C5 C3 69.4(2) . . . . ?
C6 C10 C17 C23 0.8(4) . . . . ?
C6 C13 C25 C23 1.3(5) . . . . ?
C7 C2 C5 N2 152.25(16) . . . . ?
C7 C2 C5 C1 32.5(2) . . . . ?
C7 C2 C5 C3 -80.4(2) . . . . ?
C7 C2 C8 N4 -142.1(2) . . . . ?
C7 C2 C8 C22 49.2(3) . . . . ?
C7 C11 C21 C20 -0.9(4) . . . . ?
C7 C16 C24 C20 -0.9(5) . . . . ?
C8 C2 C5 N2 21.62(17) . . . . ?
C8 C2 C5 C1 -98.08(18) . . . . ?
C8 C2 C5 C3 148.95(16) . . . . ?
C8 C2 C7 C11 34.0(3) . . . . ?
C8 C2 C7 C16 -148.6(2) . . . . ?
C9 C4 C12 C19 -0.2(3) . . . . ?
C9 C14 C18 C19 -1.4(4) . . . . ?
C10 C6 C13 C25 -2.1(4) . . . . ?
C10 C17 C23 C25 -1.6(5) . . . . ?
C11 C7 C16 C24 1.1(4) . . . . ?
C12 C4 C9 C14 -1.3(3) . . . . ?
C13 C6 C10 C17 1.1(4) . . . . ?
C14 C18 C19 C12 -0.1(5) . . . . ?
C15 C3 C5 N2 53.2(3) . . . . ?
C15 C3 C5 C1 176.1(2) . . . . ?
C15 C3 C5 C2 -64.0(3) . . . . ?
C16 C7 C11 C21 -0.2(3) . . . . ?
C17 C23 C25 C13 0.6(5) . . . . ?
C21 C20 C24 C16 -0.2(5) . . . . ?
C24 C20 C21 C11 1.1(5) . . . . ?

_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 3.624
_oxdiff_exptl_absorpt_empirical_full_min 0.571
####################################################################### 
# 
# 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_fy_0328_auto
_database_code_depnum_ccdc_archive 'CCDC 2253537'
loop_
_audit_author_name
_audit_author_address
lixiaoyong
;NWNU
China
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_audit_creation_date             2023-03-28
_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         'C25 H18 Cl2 F2 N4 O'
_chemical_formula_sum            'C25 H18 Cl2 F2 N4 O'
_chemical_formula_weight         499.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.8243(4)
_cell_length_b                   7.18030(10)
_cell_length_c                   16.7155(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.020(2)
_cell_angle_gamma                90
_cell_volume                     2308.48(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11936
_cell_measurement_temperature    274.7(3)
_cell_measurement_theta_max      76.0480
_cell_measurement_theta_min      2.7180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44383
_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    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_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  0.0407
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14610
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.382
_diffrn_reflns_theta_min         5.382
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      274.7(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    134.00 173.00   0.50    0.05    --  109.62  45.00 150.00   78
  2  ω    135.00 162.00   0.50    0.05    --  109.62 125.00  90.00   54
  3  ω     81.00 122.00   0.50    0.05    --  109.62 125.00  90.00   82
  4  ω    100.00 125.00   0.50    0.05    --  109.62 123.00 -13.00   50
  5  ω     60.00 117.00   0.50    0.05    --   44.26 148.00 150.00  114
  6  ω     91.00 118.00   0.50    0.05    --  109.62  45.00 150.00   54
  7  ω   -174.00 -74.00   0.50    0.05    -- -100.00 -77.00 -90.00  200
  8  ω   -132.00 -89.00   0.50    0.05    -- -100.00-125.00-150.00   86
  9  ω   -153.00-128.00   0.50    0.05    -- -100.00-123.00 -93.00   50
 10  ω   -117.00 -69.00   0.50    0.05    --  -44.26-148.00 102.00   96
 11  ω   -128.00-102.00   0.50    0.05    -- -100.00 148.00 150.00   52
 12  ω    -94.00 -50.00   0.50    0.05    --  -44.26 123.00 -13.00   88
 13  ω   -109.00 -35.00   0.50    0.05    -- -100.00  77.00   0.00  148
 14  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00 150.00   50
 15  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00  30.00   50
 16  ω    -54.00 -27.00   0.50    0.05    -- -100.00  61.00-150.00   54
 17  ω    -53.00 -28.00   0.50    0.05    -- -100.00  45.00-150.00   50
 18  ω    -53.00 -25.00   0.50    0.05    -- -100.00  45.00-180.00   56
 19  ω    -32.00  39.00   0.50    0.05    --   44.26 -37.00 -60.00  142
 20  ω    -18.00  23.00   0.50    0.05    --   44.26 -19.00 -30.00   82
 21  ω    -30.00  -3.00   0.50    0.05    --   44.26 -19.00 -90.00   54
 22  ω    -28.00  -3.00   0.50    0.05    --   44.26 -19.00-120.00   50
 23  ω     54.00  80.00   0.50    0.05    --   44.26-123.00 -93.00   52
 24  ω     37.00 107.00   0.50    0.05    --  109.62-123.00 -93.00  140
 25  ω     57.00 107.00   0.50    0.05    --  109.62-125.00 -30.00  100
 26  ω     62.00 128.00   0.50    0.05    --  109.62-148.00 102.00  132
;
_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      0.0626219000
_diffrn_orient_matrix_UB_12      -0.1283177000
_diffrn_orient_matrix_UB_13      0.0342479000
_diffrn_orient_matrix_UB_21      0.0485778000
_diffrn_orient_matrix_UB_22      0.1706154000
_diffrn_orient_matrix_UB_23      0.0146697000
_diffrn_orient_matrix_UB_31      -0.0116085000
_diffrn_orient_matrix_UB_32      0.0216543000
_diffrn_orient_matrix_UB_33      0.0873664000
_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                4214
_reflns_number_total             4553
_reflns_odcompleteness_completeness 99.27
_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 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4553
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0894P)²+0.6323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1410
_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:
 C8(H8), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C13(H13), C14(H14), C16(H16), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.49634(3) 0.37955(8) 0.40333(3) 0.05760(18) Uani 1 1 d . . . . .
Cl2 Cl 0.45803(3) 0.39395(8) 0.07404(3) 0.05870(18) Uani 1 1 d . . . . .
F1 F 0.07876(8) 0.6250(2) 0.08188(9) 0.0767(5) Uani 1 1 d . . . . .
F2 F 0.08160(8) 0.9263(3) 0.08993(10) 0.0813(5) Uani 1 1 d . . . . .
O1 O 0.21892(7) 0.41685(16) 0.29786(8) 0.0409(3) Uani 1 1 d . . . . .
N1 N 0.29495(8) 0.7782(2) 0.42838(9) 0.0374(3) Uani 1 1 d . . . . .
N2 N 0.28863(7) 0.7087(2) 0.21818(8) 0.0337(3) Uani 1 1 d . . . . .
N3 N 0.23845(7) 0.7010(2) 0.14420(8) 0.0347(3) Uani 1 1 d . . . . .
N4 N 0.26033(8) 0.60435(19) 0.41188(9) 0.0358(3) Uani 1 1 d . . . . .
C1 C 0.25664(8) 0.7418(2) 0.28714(9) 0.0298(3) Uani 1 1 d . . . . .
C2 C 0.38934(9) 0.5513(2) 0.30174(11) 0.0363(4) Uani 1 1 d . . . . .
H2 H 0.375650 0.583446 0.349346 0.044 Uiso 1 1 calc R . . . .
C3 C 0.24186(8) 0.5625(2) 0.32979(10) 0.0317(3) Uani 1 1 d . . . . .
C4 C 0.18157(9) 0.7651(2) 0.15612(10) 0.0349(3) Uani 1 1 d . . . . .
C5 C 0.29611(8) 0.8545(2) 0.35973(10) 0.0336(3) Uani 1 1 d . . . . .
C6 C 0.37099(9) 0.5581(2) 0.15339(11) 0.0363(4) Uani 1 1 d . . . . .
H6 H 0.345137 0.594131 0.101565 0.044 Uiso 1 1 calc R . . . .
C7 C 0.34958(8) 0.6044(2) 0.22452(10) 0.0325(3) Uani 1 1 d . . . . .
C8 C 0.18738(8) 0.8408(2) 0.24183(10) 0.0328(3) Uani 1 1 d . . . . .
H8 H 0.197686 0.974074 0.240135 0.039 Uiso 1 1 calc R . . . .
C9 C 0.25544(10) 0.4893(2) 0.47907(10) 0.0376(4) Uani 1 1 d . . . . .
C10 C 0.12828(8) 0.8218(3) 0.28371(10) 0.0371(4) Uani 1 1 d . . . . .
C11 C 0.43175(10) 0.4571(2) 0.16224(11) 0.0401(4) Uani 1 1 d . . . . .
C12 C 0.44964(9) 0.4497(2) 0.30648(11) 0.0394(4) Uani 1 1 d . . . . .
C13 C 0.30991(12) 0.4852(3) 0.54877(12) 0.0500(5) Uani 1 1 d . . . . .
H13 H 0.350294 0.552889 0.550776 0.060 Uiso 1 1 calc R . . . .
C14 C 0.47217(10) 0.4004(3) 0.23776(12) 0.0430(4) Uani 1 1 d . . . . .
H14 H 0.512726 0.332127 0.241912 0.052 Uiso 1 1 calc R . . . .
C15 C 0.33015(11) 1.0367(3) 0.35453(13) 0.0501(5) Uani 1 1 d . . . . .
H15A H 0.350736 1.081342 0.409116 0.075 Uiso 1 1 calc GR . . . .
H15B H 0.296131 1.124637 0.326329 0.075 Uiso 1 1 calc GR . . . .
H15C H 0.365585 1.021944 0.324767 0.075 Uiso 1 1 calc GR . . . .
C16 C 0.08600(10) 0.6649(3) 0.27434(12) 0.0474(4) Uani 1 1 d . . . . .
H16 H 0.092362 0.569147 0.239438 0.057 Uiso 1 1 calc R . . . .
C17 C 0.12000(10) 0.7752(3) 0.08347(12) 0.0462(4) Uani 1 1 d . . . . .
H17 H 0.135778 0.781489 0.032318 0.055 Uiso 1 1 calc R . . . .
C18 C 0.11750(11) 0.9630(3) 0.33554(12) 0.0507(5) Uani 1 1 d . . . . .
H18 H 0.145157 1.069209 0.341846 0.061 Uiso 1 1 calc R . . . .
C19 C 0.19586(13) 0.3858(3) 0.47477(14) 0.0526(5) Uani 1 1 d . . . . .
H19 H 0.159579 0.388096 0.427577 0.063 Uiso 1 1 calc R . . . .
C20 C 0.02455(11) 0.7922(5) 0.36879(14) 0.0681(7) Uani 1 1 d . . . . .
H20 H -0.010069 0.781946 0.397434 0.082 Uiso 1 1 calc R . . . .
C21 C 0.30325(17) 0.3787(3) 0.61546(14) 0.0644(7) Uani 1 1 d . . . . .
H21 H 0.339239 0.376198 0.662939 0.077 Uiso 1 1 calc R . . . .
C22 C 0.03424(11) 0.6513(4) 0.31715(14) 0.0612(6) Uani 1 1 d . . . . .
H22 H 0.005996 0.546295 0.310780 0.073 Uiso 1 1 calc R . . . .
C23 C 0.06575(13) 0.9477(4) 0.37824(14) 0.0670(7) Uani 1 1 d . . . . .
H23 H 0.059072 1.042946 0.413229 0.080 Uiso 1 1 calc R . . . .
C24 C 0.24413(19) 0.2766(3) 0.61225(15) 0.0721(8) Uani 1 1 d . . . . .
H24 H 0.239970 0.206408 0.657555 0.087 Uiso 1 1 calc R . . . .
C25 C 0.19129(17) 0.2785(3) 0.54223(17) 0.0705(7) Uani 1 1 d . . . . .
H25 H 0.151782 0.206812 0.539861 0.085 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
Cl1 C12 1.7336(19) . ?
Cl2 C11 1.7386(17) . ?
F1 C17 1.350(2) . ?
F2 C17 1.345(3) . ?
O1 C3 1.211(2) . ?
N1 N4 1.4191(19) . ?
N1 C5 1.277(2) . ?
N2 N3 1.3878(19) . ?
N2 C1 1.4634(19) . ?
N2 C7 1.403(2) . ?
N3 C4 1.278(2) . ?
N4 C3 1.365(2) . ?
N4 C9 1.416(2) . ?
C1 C3 1.534(2) . ?
C1 C5 1.510(2) . ?
C1 C8 1.569(2) . ?
C2 C7 1.393(2) . ?
C2 C12 1.386(2) . ?
C4 C8 1.511(2) . ?
C4 C17 1.500(2) . ?
C5 C15 1.484(2) . ?
C6 C7 1.396(2) . ?
C6 C11 1.383(3) . ?
C8 C10 1.510(2) . ?
C9 C13 1.384(3) . ?
C9 C19 1.382(3) . ?
C10 C16 1.390(3) . ?
C10 C18 1.384(3) . ?
C11 C14 1.382(3) . ?
C12 C14 1.376(3) . ?
C13 C21 1.385(3) . ?
C16 C22 1.389(3) . ?
C18 C23 1.389(3) . ?
C19 C25 1.387(3) . ?
C20 C22 1.373(4) . ?
C20 C23 1.370(4) . ?
C21 C24 1.372(4) . ?
C24 C25 1.369(4) . ?

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
C5 N1 N4 108.42(13) . . ?
N3 N2 C1 110.76(12) . . ?
N3 N2 C7 117.66(13) . . ?
C7 N2 C1 123.81(13) . . ?
C4 N3 N2 108.41(13) . . ?
C3 N4 N1 112.85(13) . . ?
C3 N4 C9 127.98(14) . . ?
C9 N4 N1 118.80(13) . . ?
N2 C1 C3 113.45(12) . . ?
N2 C1 C5 118.74(13) . . ?
N2 C1 C8 100.89(12) . . ?
C3 C1 C8 111.19(13) . . ?
C5 C1 C3 101.34(12) . . ?
C5 C1 C8 111.55(12) . . ?
C12 C2 C7 118.93(15) . . ?
O1 C3 N4 127.85(15) . . ?
O1 C3 C1 127.83(14) . . ?
N4 C3 C1 104.32(13) . . ?
N3 C4 C8 114.22(14) . . ?
N3 C4 C17 117.82(15) . . ?
C17 C4 C8 127.63(15) . . ?
N1 C5 C1 111.93(14) . . ?
N1 C5 C15 122.57(16) . . ?
C15 C5 C1 125.45(15) . . ?
C11 C6 C7 118.06(16) . . ?
C2 C7 N2 119.99(14) . . ?
C2 C7 C6 120.23(15) . . ?
C6 C7 N2 119.77(15) . . ?
C4 C8 C1 98.71(12) . . ?
C10 C8 C1 114.96(13) . . ?
C10 C8 C4 121.18(14) . . ?
C13 C9 N4 119.37(18) . . ?
C19 C9 N4 119.60(17) . . ?
C19 C9 C13 121.01(18) . . ?
C16 C10 C8 122.39(16) . . ?
C18 C10 C8 118.62(17) . . ?
C18 C10 C16 118.95(17) . . ?
C6 C11 Cl2 118.58(15) . . ?
C14 C11 Cl2 118.10(14) . . ?
C14 C11 C6 123.31(16) . . ?
C2 C12 Cl1 117.68(14) . . ?
C14 C12 Cl1 119.80(14) . . ?
C14 C12 C2 122.50(17) . . ?
C9 C13 C21 118.8(2) . . ?
C12 C14 C11 116.95(16) . . ?
C22 C16 C10 120.0(2) . . ?
F1 C17 C4 110.34(16) . . ?
F2 C17 F1 107.10(17) . . ?
F2 C17 C4 109.83(16) . . ?
C10 C18 C23 120.6(2) . . ?
C9 C19 C25 118.7(2) . . ?
C23 C20 C22 120.2(2) . . ?
C24 C21 C13 120.7(2) . . ?
C20 C22 C16 120.4(2) . . ?
C20 C23 C18 120.0(2) . . ?
C25 C24 C21 119.9(2) . . ?
C24 C25 C19 120.9(3) . . ?

_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 2.260
_oxdiff_exptl_absorpt_empirical_full_min 0.558
####################################################################### 
# 
# 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_a-21-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2253536'
loop_
_audit_author_name
_audit_author_address
Lixiaoyong
;NWNU
China
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_audit_creation_date             2022-07-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C25 H18 Cl2 F2 N4 O)'
_chemical_formula_sum            'C50 H36 Cl4 F4 N8 O2'
_chemical_formula_weight         998.67
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   18.9993(2)
_cell_length_b                   11.37225(15)
_cell_length_c                   43.5762(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.9104(11)
_cell_angle_gamma                90
_cell_volume                     9346.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15359
_cell_measurement_temperature    301.71(10)
_cell_measurement_theta_max      76.3870
_cell_measurement_theta_min      2.0360
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.783
_exptl_absorpt_coefficient_mu    2.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31568
_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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4096
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            30745
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.401
_diffrn_reflns_theta_min         2.043
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.71(10)
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  17.00   0.50    0.05    --   47.45 -19.00   0.00   84
  2  ω    -22.00  23.00   0.50    0.05    --   47.45 -19.00  30.00   90
  3  ω     95.00 156.00   0.50    0.05    --  107.75 105.00-130.00  122
  4  ω     76.00 102.00   0.50    0.05    --  107.75 -77.00 120.00   52
  5  ω     39.00  68.00   0.50    0.05    --  107.75 -77.00 120.00   58
  6  ω     37.00  62.00   0.50    0.05    --  107.75 -57.00 150.00   50
  7  ω     35.00  62.00   0.50    0.05    --  107.75 -57.00 120.00   54
  8  ω     37.00  62.00   0.50    0.05    --  107.75 -57.00   0.00   50
  9  ω     53.00  79.00   0.50    0.05    --  107.75 -77.00-180.00   52
 10  ω     35.00  63.00   0.50    0.05    --  107.75 -57.00 -90.00   56
 11  ω     38.00  63.00   0.50    0.05    --  107.75 -57.00 -60.00   50
 12  ω     28.00  56.00   0.50    0.05    --   47.45-105.00 128.00   56
 13  ω     55.00 106.00   0.50    0.05    --  107.75-105.00 128.00  102
 14  ω    -15.00  26.00   0.50    0.05    --  -47.45  37.00  90.00   82
 15  ω    -59.00 -27.00   0.50    0.05    -- -100.00 125.00 -90.00   64
 16  ω   -103.00 -61.00   0.50    0.05    -- -100.00 105.00-130.00   84
 17  ω    -80.00 -14.00   0.50    0.05    --  -47.45 105.00-130.00  132
 18  ω    -66.00 -27.00   0.50    0.05    -- -100.00  57.00-150.00   78
 19  ω    -63.00 -36.00   0.50    0.05    -- -100.00  57.00-180.00   54
 20  ω    -68.00 -28.00   0.50    0.05    -- -100.00  57.00  30.00   80
 21  ω    -66.00 -34.00   0.50    0.05    -- -100.00  57.00  60.00   64
 22  ω    -61.00 -32.00   0.50    0.05    -- -100.00  57.00  90.00   58
 23  ω   -120.00 -43.00   0.50    0.05    --  -47.45 -57.00 150.00  154
 24  ω   -162.00-107.00   0.50    0.05    -- -100.00-105.00 128.00  110
 25  ω   -172.00 -99.00   0.50    0.05    -- -100.00-125.00-180.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0055404000
_diffrn_orient_matrix_UB_12      0.1306408000
_diffrn_orient_matrix_UB_13      0.0093368000
_diffrn_orient_matrix_UB_21      0.0803901000
_diffrn_orient_matrix_UB_22      -0.0030142000
_diffrn_orient_matrix_UB_23      -0.0019544000
_diffrn_orient_matrix_UB_31      -0.0133194000
_diffrn_orient_matrix_UB_32      0.0357434000
_diffrn_orient_matrix_UB_33      -0.0343130000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7295
_reflns_number_total             9322
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         9322
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.159
_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)+(0.1236P)²+3.5605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1957
_refine_ls_wR_factor_ref         0.2087
_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. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C49)
\\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3) \\sim Ueq: with
sigma of 0.01 and sigma for terminal atoms of 0.005
3.a Ternary CH refined with riding coordinates:
 C4(H4), C48(H48), C2(H2), C44(H44)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C17(H17), C18(H18), C21(H21), C35(H35), C36(H36),
 C37(H37), C41(H41), C42(H42), C43(H43), C45(H45), C46(H46), C15(H15), C20(H20),
  C23(H23), C25(H25), C29(H29), C30(H30), C33(H33), C38(H38), C39(H39),
 C40(H40), C47(H47), C49(H49), C50(H50)
3.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.54816(4) 0.81154(8) 0.62818(2) 0.0917(3) Uani 1 1 d . . . . .
Cl2 Cl 0.47037(5) 1.12412(6) 0.70962(2) 0.0969(3) Uani 1 1 d . . . . .
F1 F 0.33935(13) 0.5307(2) 0.79775(4) 0.1076(7) Uani 1 1 d . U . . .
F4 F 0.25358(15) 0.6359(3) 0.78035(6) 0.1474(10) Uani 1 1 d . U . . .
O1 O 0.50389(9) 0.46195(17) 0.71294(4) 0.0675(4) Uani 1 1 d . . . . .
N2 N 0.42871(9) 0.45225(16) 0.66719(4) 0.0514(4) Uani 1 1 d . . . . .
N4 N 0.41377(12) 0.68758(17) 0.71739(4) 0.0606(5) Uani 1 1 d . . . . .
N5 N 0.36581(10) 0.50801(17) 0.65388(4) 0.0540(4) Uani 1 1 d . . . . .
N8 N 0.38307(12) 0.71429(18) 0.74341(4) 0.0650(5) Uani 1 1 d . . . . .
C3 C 0.39178(11) 0.57296(18) 0.70450(4) 0.0501(4) Uani 1 1 d . . . . .
C4 C 0.35805(12) 0.51584(19) 0.73226(4) 0.0518(5) Uani 1 1 d . . . . .
H4 H 0.394934 0.467131 0.743652 0.062 Uiso 1 1 calc R U . . .
C5 C 0.34511(11) 0.57779(19) 0.67391(5) 0.0516(5) Uani 1 1 d . . . . .
C7 C 0.29494(12) 0.4366(2) 0.72332(5) 0.0553(5) Uani 1 1 d . . . . .
C10 C 0.46131(11) 0.36918(19) 0.64910(4) 0.0510(5) Uani 1 1 d . . . . .
C11 C 0.41926(14) 0.3030(2) 0.62781(6) 0.0692(6) Uani 1 1 d . . . . .
H11 H 0.370244 0.311586 0.625734 0.083 Uiso 1 1 calc R U . . .
C12 C 0.30730(16) 0.3197(2) 0.71683(5) 0.0687(6) Uani 1 1 d . . . . .
H12 H 0.353698 0.292218 0.718280 0.082 Uiso 1 1 calc R U . . .
C13 C 0.44381(12) 0.7784(2) 0.70161(5) 0.0550(5) Uani 1 1 d . . . . .
C17 C 0.50610(13) 0.9578(2) 0.67040(6) 0.0693(7) Uani 1 1 d . . . . .
H17 H 0.526356 1.017895 0.659941 0.083 Uiso 1 1 calc R U . . .
C18 C 0.44244(13) 0.8930(2) 0.71256(5) 0.0613(5) Uani 1 1 d . . . . .
H18 H 0.421298 0.910491 0.730178 0.074 Uiso 1 1 calc R U . . .
C19 C 0.50737(12) 0.8434(2) 0.66060(5) 0.0625(6) Uani 1 1 d . . . . .
C21 C 0.47653(12) 0.7528(2) 0.67539(5) 0.0601(5) Uani 1 1 d . . . . .
H21 H 0.477569 0.676185 0.667994 0.072 Uiso 1 1 calc R U . . .
C22 C 0.35036(14) 0.6239(2) 0.75157(5) 0.0617(6) Uani 1 1 d . . . . .
C24 C 0.45131(11) 0.49077(19) 0.69636(4) 0.0506(5) Uani 1 1 d . . . . .
C27 C 0.28424(14) 0.6589(2) 0.66641(5) 0.0664(6) Uani 1 1 d . . . . .
H27A H 0.265465 0.649628 0.645095 0.100 Uiso 1 1 calc R U . . .
H27B H 0.299856 0.738589 0.670000 0.100 Uiso 1 1 calc R U . . .
H27C H 0.248058 0.641090 0.679289 0.100 Uiso 1 1 calc R U . . .
C31 C 0.47323(14) 0.9802(2) 0.69665(6) 0.0663(6) Uani 1 1 d . . . . .
C35 C 0.56432(16) 0.2758(3) 0.63386(7) 0.0843(8) Uani 1 1 d . . . . .
H35 H 0.613324 0.266947 0.635899 0.101 Uiso 1 1 calc R U . . .
C36 C 0.52266(17) 0.2103(3) 0.61255(6) 0.0801(8) Uani 1 1 d . . . . .
H36 H 0.543194 0.156842 0.600141 0.096 Uiso 1 1 calc R U . . .
C37 C 0.53393(13) 0.3556(3) 0.65247(6) 0.0705(7) Uani 1 1 d . . . . .
H37 H 0.562341 0.399548 0.667098 0.085 Uiso 1 1 calc R U . . .
C41 C 0.44999(17) 0.2238(3) 0.60954(6) 0.0803(8) Uani 1 1 d . . . . .
H41 H 0.421562 0.179100 0.595081 0.096 Uiso 1 1 calc R U . . .
C42 C 0.22555(14) 0.4762(3) 0.72134(7) 0.0757(7) Uani 1 1 d . . . . .
H42 H 0.215653 0.554043 0.725738 0.091 Uiso 1 1 calc R U . . .
C43 C 0.2520(2) 0.2430(3) 0.70822(7) 0.0895(9) Uani 1 1 d . . . . .
H43 H 0.261441 0.164826 0.704004 0.107 Uiso 1 1 calc R U . . .
C45 C 0.17008(17) 0.3955(4) 0.71246(8) 0.0952(11) Uani 1 1 d . . . . .
H45 H 0.123191 0.420509 0.711049 0.114 Uiso 1 1 calc R U . . .
C46 C 0.1849(2) 0.2807(4) 0.70593(8) 0.0969(10) Uani 1 1 d . . . . .
H46 H 0.148041 0.228780 0.699856 0.116 Uiso 1 1 calc R U . . .
C48 C 0.3211(2) 0.6286(3) 0.78201(7) 0.0849(9) Uani 1 1 d . . . . .
H48 H 0.342031 0.695995 0.793781 0.102 Uiso 1 1 calc R U . . .
Cl3 Cl 0.18060(7) 0.43567(11) 0.61762(2) 0.1351(5) Uani 1 1 d . . . . .
Cl4 Cl 0.28137(6) 0.12051(8) 0.54366(3) 0.1219(4) Uani 1 1 d . . . . .
F2 F 0.40972(14) 0.7168(2) 0.45236(5) 0.1284(9) Uani 1 1 d . U . . .
F3 F 0.48937(12) 0.6017(3) 0.47125(5) 0.1236(8) Uani 1 1 d . U . . .
O2 O 0.24053(8) 0.79255(19) 0.53816(3) 0.0749(5) Uani 1 1 d . . . . .
N1 N 0.31652(9) 0.79041(16) 0.58358(3) 0.0493(4) Uani 1 1 d . . . . .
N3 N 0.37830(9) 0.72883(16) 0.59607(4) 0.0501(4) Uani 1 1 d . . . . .
N6 N 0.32276(11) 0.56083(18) 0.53125(4) 0.0615(5) Uani 1 1 d . . . . .
N7 N 0.35378(11) 0.53354(19) 0.50498(4) 0.0636(5) Uani 1 1 d . . . . .
C1 C 0.44733(12) 0.8058(2) 0.52623(5) 0.0571(5) Uani 1 1 d . . . . .
C2 C 0.38307(11) 0.72928(19) 0.51729(4) 0.0502(5) Uani 1 1 d . . . . .
H2 H 0.346672 0.779902 0.506268 0.060 Uiso 1 1 calc R U . . .
C6 C 0.34911(11) 0.67198(19) 0.54496(4) 0.0500(4) Uani 1 1 d . . . . .
C8 C 0.28759(10) 0.87631(18) 0.60196(4) 0.0463(4) Uani 1 1 d . . . . .
C9 C 0.39656(11) 0.66057(19) 0.57523(4) 0.0496(4) Uani 1 1 d . . . . .
C14 C 0.38848(12) 0.6221(2) 0.49753(5) 0.0578(5) Uani 1 1 d . . . . .
C15 C 0.33237(13) 0.9408(2) 0.62293(5) 0.0666(6) Uani 1 1 d . . . . .
H15 H 0.381030 0.927735 0.624941 0.080 Uiso 1 1 calc R U . . .
C16 C 0.29539(12) 0.4689(2) 0.54746(5) 0.0599(5) Uani 1 1 d . . . . .
C20 C 0.4366(2) 0.9232(3) 0.53248(6) 0.0819(8) Uani 1 1 d . . . . .
H20 H 0.390527 0.952126 0.531096 0.098 Uiso 1 1 calc R U . . .
C23 C 0.23535(15) 0.2883(3) 0.57930(7) 0.0803(8) Uani 1 1 d . . . . .
H23 H 0.215789 0.227999 0.589939 0.096 Uiso 1 1 calc R U . . .
C25 C 0.30304(13) 0.3527(2) 0.53856(6) 0.0679(6) Uani 1 1 d . . . . .
H25 H 0.328218 0.334271 0.522180 0.081 Uiso 1 1 calc R U . . .
C26 C 0.29249(11) 0.7570(2) 0.55416(4) 0.0516(5) Uani 1 1 d . . . . .
C28 C 0.45579(14) 0.5758(2) 0.58165(5) 0.0647(6) Uani 1 1 d . . . . .
H28A H 0.493085 0.596191 0.569588 0.097 Uiso 1 1 calc R U . . .
H28B H 0.439123 0.497934 0.576305 0.097 Uiso 1 1 calc R U . . .
H28C H 0.473519 0.578498 0.603220 0.097 Uiso 1 1 calc R U . . .
C29 C 0.18816(14) 0.9796(3) 0.61713(6) 0.0698(6) Uani 1 1 d . . . . .
H29 H 0.139512 0.992744 0.615212 0.084 Uiso 1 1 calc R U . . .
C30 C 0.25833(15) 0.4946(3) 0.57238(6) 0.0729(7) Uani 1 1 d . . . . .
H30 H 0.253695 0.571995 0.578747 0.088 Uiso 1 1 calc R U . . .
C32 C 0.27265(15) 0.2655(3) 0.55445(7) 0.0772(7) Uani 1 1 d . . . . .
C33 C 0.21530(12) 0.8953(2) 0.59898(5) 0.0599(5) Uani 1 1 d . . . . .
H33 H 0.185175 0.851676 0.584904 0.072 Uiso 1 1 calc R U . . .
C34 C 0.22866(15) 0.4041(3) 0.58744(6) 0.0789(8) Uani 1 1 d . . . . .
C38 C 0.30442(16) 1.0243(3) 0.64081(6) 0.0775(7) Uani 1 1 d . . . . .
H38 H 0.334414 1.067842 0.654958 0.093 Uiso 1 1 calc R U . . .
C39 C 0.23225(16) 1.0443(3) 0.63795(6) 0.0719(7) Uani 1 1 d . . . . .
H39 H 0.213658 1.101067 0.650053 0.086 Uiso 1 1 calc R U . . .
C40 C 0.51545(14) 0.7636(3) 0.52801(7) 0.0810(8) Uani 1 1 d . . . . .
H40 H 0.523662 0.685043 0.523750 0.097 Uiso 1 1 calc R U . . .
C44 C 0.41964(16) 0.6162(3) 0.46747(6) 0.0752(7) Uani 1 1 d . . . . .
H44 H 0.397313 0.552103 0.454772 0.090 Uiso 1 1 calc R U . . .
C47 C 0.4925(3) 0.9983(4) 0.54071(8) 0.1159(14) Uani 1 1 d . U . . .
H47 H 0.484528 1.076934 0.545035 0.139 Uiso 1 1 calc R U . . .
C49 C 0.5724(2) 0.8399(5) 0.53630(9) 0.1118(13) Uani 1 1 d . U . . .
H49 H 0.618794 0.812356 0.537653 0.134 Uiso 1 1 calc R U . . .
C50 C 0.5593(3) 0.9556(5) 0.54240(9) 0.1314(19) Uani 1 1 d . U . . .
H50 H 0.597348 1.006036 0.547834 0.158 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C19 1.730(3) . ?
Cl2 C31 1.734(3) . ?
F1 C48 1.331(4) . ?
F4 C48 1.279(4) . ?
O1 C24 1.206(3) . ?
N2 N5 1.414(2) . ?
N2 C10 1.420(3) . ?
N2 C24 1.364(3) . ?
N4 N8 1.370(3) . ?
N4 C3 1.460(3) . ?
N4 C13 1.400(3) . ?
N5 C5 1.277(3) . ?
N8 C22 1.274(3) . ?
C3 C4 1.576(3) . ?
C3 C5 1.510(3) . ?
C3 C24 1.541(3) . ?
C4 H4 0.9800 . ?
C4 C7 1.513(3) . ?
C4 C22 1.506(3) . ?
C5 C27 1.485(3) . ?
C7 C12 1.385(4) . ?
C7 C42 1.386(4) . ?
C10 C11 1.374(3) . ?
C10 C37 1.378(3) . ?
C11 H11 0.9300 . ?
C11 C41 1.377(4) . ?
C12 H12 0.9300 . ?
C12 C43 1.382(4) . ?
C13 C18 1.389(3) . ?
C13 C21 1.396(3) . ?
C17 H17 0.9300 . ?
C17 C19 1.370(4) . ?
C17 C31 1.391(4) . ?
C18 H18 0.9300 . ?
C18 C31 1.380(4) . ?
C19 C21 1.383(3) . ?
C21 H21 0.9300 . ?
C22 C48 1.500(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C35 H35 0.9300 . ?
C35 C36 1.366(4) . ?
C35 C37 1.388(4) . ?
C36 H36 0.9300 . ?
C36 C41 1.380(4) . ?
C37 H37 0.9300 . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C42 C45 1.416(5) . ?
C43 H43 0.9300 . ?
C43 C46 1.336(5) . ?
C45 H45 0.9300 . ?
C45 C46 1.373(6) . ?
C46 H46 0.9300 . ?
C48 H48 0.9800 . ?
Cl3 C34 1.727(3) . ?
Cl4 C32 1.728(3) . ?
F2 C44 1.322(4) . ?
F3 C44 1.325(4) . ?
O2 C26 1.208(3) . ?
N1 N3 1.418(2) . ?
N1 C8 1.416(2) . ?
N1 C26 1.362(2) . ?
N3 C9 1.274(3) . ?
N6 N7 1.384(3) . ?
N6 C6 1.461(3) . ?
N6 C16 1.397(3) . ?
N7 C14 1.267(3) . ?
C1 C2 1.512(3) . ?
C1 C20 1.383(4) . ?
C1 C40 1.374(4) . ?
C2 H2 0.9800 . ?
C2 C6 1.575(3) . ?
C2 C14 1.503(3) . ?
C6 C9 1.511(3) . ?
C6 C26 1.535(3) . ?
C8 C15 1.382(3) . ?
C8 C33 1.381(3) . ?
C9 C28 1.482(3) . ?
C14 C44 1.503(3) . ?
C15 H15 0.9300 . ?
C15 C38 1.376(4) . ?
C16 C25 1.389(4) . ?
C16 C30 1.394(3) . ?
C20 H20 0.9300 . ?
C20 C47 1.377(5) . ?
C23 H23 0.9300 . ?
C23 C32 1.388(4) . ?
C23 C34 1.373(4) . ?
C25 H25 0.9300 . ?
C25 C32 1.376(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29 0.9300 . ?
C29 C33 1.382(3) . ?
C29 C39 1.372(4) . ?
C30 H30 0.9300 . ?
C30 C34 1.378(4) . ?
C33 H33 0.9300 . ?
C38 H38 0.9300 . ?
C38 C39 1.380(4) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C40 C49 1.401(5) . ?
C44 H44 0.9800 . ?
C47 H47 0.9300 . ?
C47 C50 1.353(7) . ?
C49 H49 0.9300 . ?
C49 C50 1.371(7) . ?
C50 H50 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
N5 N2 C10 118.31(16) . . ?
C24 N2 N5 113.21(16) . . ?
C24 N2 C10 128.44(18) . . ?
N8 N4 C3 112.68(18) . . ?
N8 N4 C13 118.83(19) . . ?
C13 N4 C3 125.75(17) . . ?
C5 N5 N2 108.22(16) . . ?
C22 N8 N4 108.82(19) . . ?
N4 C3 C4 101.34(15) . . ?
N4 C3 C5 114.67(17) . . ?
N4 C3 C24 116.49(18) . . ?
C5 C3 C4 116.28(17) . . ?
C5 C3 C24 100.84(16) . . ?
C24 C3 C4 107.71(17) . . ?
C3 C4 H4 106.8 . . ?
C7 C4 C3 115.52(16) . . ?
C7 C4 H4 106.8 . . ?
C22 C4 C3 99.68(17) . . ?
C22 C4 H4 106.8 . . ?
C22 C4 C7 120.18(19) . . ?
N5 C5 C3 112.62(18) . . ?
N5 C5 C27 122.11(19) . . ?
C27 C5 C3 125.16(19) . . ?
C12 C7 C4 118.4(2) . . ?
C12 C7 C42 118.8(3) . . ?
C42 C7 C4 122.7(2) . . ?
C11 C10 N2 118.9(2) . . ?
C11 C10 C37 120.2(2) . . ?
C37 C10 N2 120.9(2) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C41 119.7(2) . . ?
C41 C11 H11 120.1 . . ?
C7 C12 H12 119.4 . . ?
C43 C12 C7 121.2(3) . . ?
C43 C12 H12 119.4 . . ?
C18 C13 N4 119.9(2) . . ?
C18 C13 C21 120.4(2) . . ?
C21 C13 N4 119.7(2) . . ?
C19 C17 H17 121.4 . . ?
C19 C17 C31 117.2(2) . . ?
C31 C17 H17 121.4 . . ?
C13 C18 H18 120.8 . . ?
C31 C18 C13 118.4(2) . . ?
C31 C18 H18 120.8 . . ?
C17 C19 Cl1 118.69(19) . . ?
C17 C19 C21 122.6(2) . . ?
C21 C19 Cl1 118.7(2) . . ?
C13 C21 H21 120.6 . . ?
C19 C21 C13 118.8(2) . . ?
C19 C21 H21 120.6 . . ?
N8 C22 C4 114.8(2) . . ?
N8 C22 C48 117.6(2) . . ?
C48 C22 C4 126.4(2) . . ?
O1 C24 N2 128.0(2) . . ?
O1 C24 C3 127.23(19) . . ?
N2 C24 C3 104.58(17) . . ?
C5 C27 H27A 109.5 . . ?
C5 C27 H27B 109.5 . . ?
C5 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17 C31 Cl2 118.4(2) . . ?
C18 C31 Cl2 118.9(2) . . ?
C18 C31 C17 122.7(2) . . ?
C36 C35 H35 119.8 . . ?
C36 C35 C37 120.4(3) . . ?
C37 C35 H35 119.8 . . ?
C35 C36 H36 120.2 . . ?
C35 C36 C41 119.7(2) . . ?
C41 C36 H36 120.2 . . ?
C10 C37 C35 119.5(2) . . ?
C10 C37 H37 120.2 . . ?
C35 C37 H37 120.2 . . ?
C11 C41 C36 120.4(3) . . ?
C11 C41 H41 119.8 . . ?
C36 C41 H41 119.8 . . ?
C7 C42 H42 120.7 . . ?
C7 C42 C45 118.5(3) . . ?
C45 C42 H42 120.7 . . ?
C12 C43 H43 119.8 . . ?
C46 C43 C12 120.3(3) . . ?
C46 C43 H43 119.8 . . ?
C42 C45 H45 119.7 . . ?
C46 C45 C42 120.5(3) . . ?
C46 C45 H45 119.7 . . ?
C43 C46 C45 120.5(3) . . ?
C43 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
F1 C48 C22 108.9(2) . . ?
F1 C48 H48 108.7 . . ?
F4 C48 F1 106.3(3) . . ?
F4 C48 C22 115.4(3) . . ?
F4 C48 H48 108.7 . . ?
C22 C48 H48 108.7 . . ?
C8 N1 N3 118.91(15) . . ?
C26 N1 N3 113.06(16) . . ?
C26 N1 C8 128.03(17) . . ?
C9 N3 N1 108.13(15) . . ?
N7 N6 C6 111.92(18) . . ?
N7 N6 C16 118.15(19) . . ?
C16 N6 C6 124.82(17) . . ?
C14 N7 N6 108.66(19) . . ?
C20 C1 C2 118.2(2) . . ?
C40 C1 C2 122.7(2) . . ?
C40 C1 C20 119.1(3) . . ?
C1 C2 H2 106.8 . . ?
C1 C2 C6 115.68(15) . . ?
C6 C2 H2 106.8 . . ?
C14 C2 C1 120.38(18) . . ?
C14 C2 H2 106.8 . . ?
C14 C2 C6 99.54(17) . . ?
N6 C6 C2 101.34(15) . . ?
N6 C6 C9 114.96(18) . . ?
N6 C6 C26 115.81(18) . . ?
C9 C6 C2 116.56(17) . . ?
C9 C6 C26 100.92(15) . . ?
C26 C6 C2 107.69(17) . . ?
C15 C8 N1 119.36(19) . . ?
C33 C8 N1 120.26(18) . . ?
C33 C8 C15 120.4(2) . . ?
N3 C9 C6 112.63(17) . . ?
N3 C9 C28 121.81(18) . . ?
C28 C9 C6 125.48(18) . . ?
N7 C14 C2 115.09(19) . . ?
N7 C14 C44 117.3(2) . . ?
C44 C14 C2 126.7(2) . . ?
C8 C15 H15 120.3 . . ?
C38 C15 C8 119.5(2) . . ?
C38 C15 H15 120.3 . . ?
C25 C16 N6 120.9(2) . . ?
C25 C16 C30 119.8(2) . . ?
C30 C16 N6 119.4(2) . . ?
C1 C20 H20 119.2 . . ?
C47 C20 C1 121.5(4) . . ?
C47 C20 H20 119.2 . . ?
C32 C23 H23 121.6 . . ?
C34 C23 H23 121.6 . . ?
C34 C23 C32 116.9(3) . . ?
C16 C25 H25 120.6 . . ?
C32 C25 C16 118.7(3) . . ?
C32 C25 H25 120.6 . . ?
O2 C26 N1 127.4(2) . . ?
O2 C26 C6 127.59(18) . . ?
N1 C26 C6 104.80(16) . . ?
C9 C28 H28A 109.5 . . ?
C9 C28 H28B 109.5 . . ?
C9 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C33 C29 H29 119.7 . . ?
C39 C29 H29 119.7 . . ?
C39 C29 C33 120.7(2) . . ?
C16 C30 H30 120.4 . . ?
C34 C30 C16 119.2(3) . . ?
C34 C30 H30 120.4 . . ?
C23 C32 Cl4 117.7(2) . . ?
C25 C32 Cl4 119.4(3) . . ?
C25 C32 C23 122.9(3) . . ?
C8 C33 C29 119.3(2) . . ?
C8 C33 H33 120.3 . . ?
C29 C33 H33 120.3 . . ?
C23 C34 Cl3 118.0(2) . . ?
C23 C34 C30 122.5(3) . . ?
C30 C34 Cl3 119.5(3) . . ?
C15 C38 H38 119.7 . . ?
C15 C38 C39 120.6(2) . . ?
C39 C38 H38 119.7 . . ?
C29 C39 C38 119.5(2) . . ?
C29 C39 H39 120.2 . . ?
C38 C39 H39 120.2 . . ?
C1 C40 H40 120.3 . . ?
C1 C40 C49 119.5(4) . . ?
C49 C40 H40 120.3 . . ?
F2 C44 F3 104.5(3) . . ?
F2 C44 C14 110.3(2) . . ?
F2 C44 H44 109.7 . . ?
F3 C44 C14 112.9(2) . . ?
F3 C44 H44 109.7 . . ?
C14 C44 H44 109.7 . . ?
C20 C47 H47 120.6 . . ?
C50 C47 C20 118.8(4) . . ?
C50 C47 H47 120.6 . . ?
C40 C49 H49 120.3 . . ?
C50 C49 C40 119.5(4) . . ?
C50 C49 H49 120.3 . . ?
C47 C50 C49 121.7(4) . . ?
C47 C50 H50 119.2 . . ?
C49 C50 H50 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C19 C21 C13 179.79(17) . . . . ?
N2 N5 C5 C3 -2.4(2) . . . . ?
N2 N5 C5 C27 173.9(2) . . . . ?
N2 C10 C11 C41 178.5(2) . . . . ?
N2 C10 C37 C35 -178.3(3) . . . . ?
N4 N8 C22 C4 3.4(3) . . . . ?
N4 N8 C22 C48 171.9(2) . . . . ?
N4 C3 C4 C7 145.27(19) . . . . ?
N4 C3 C4 C22 15.0(2) . . . . ?
N4 C3 C5 N5 131.9(2) . . . . ?
N4 C3 C5 C27 -44.4(3) . . . . ?
N4 C3 C24 O1 52.3(3) . . . . ?
N4 C3 C24 N2 -131.69(18) . . . . ?
N4 C13 C18 C31 179.3(2) . . . . ?
N4 C13 C21 C19 -178.4(2) . . . . ?
N5 N2 C10 C11 -32.0(3) . . . . ?
N5 N2 C10 C37 147.3(2) . . . . ?
N5 N2 C24 O1 -177.7(2) . . . . ?
N5 N2 C24 C3 6.3(2) . . . . ?
N8 N4 C3 C4 -15.3(2) . . . . ?
N8 N4 C3 C5 110.8(2) . . . . ?
N8 N4 C3 C24 -131.8(2) . . . . ?
N8 N4 C13 C18 0.4(3) . . . . ?
N8 N4 C13 C21 178.8(2) . . . . ?
N8 C22 C48 F1 -132.1(3) . . . . ?
N8 C22 C48 F4 108.4(4) . . . . ?
C3 N4 N8 C22 8.4(3) . . . . ?
C3 N4 C13 C18 160.2(2) . . . . ?
C3 N4 C13 C21 -21.4(3) . . . . ?
C3 C4 C7 C12 85.6(2) . . . . ?
C3 C4 C7 C42 -94.3(3) . . . . ?
C3 C4 C22 N8 -12.2(3) . . . . ?
C3 C4 C22 C48 -179.6(3) . . . . ?
C4 C3 C5 N5 -110.2(2) . . . . ?
C4 C3 C5 C27 73.6(3) . . . . ?
C4 C3 C24 O1 -60.6(3) . . . . ?
C4 C3 C24 N2 115.37(18) . . . . ?
C4 C7 C12 C43 -179.3(2) . . . . ?
C4 C7 C42 C45 179.3(2) . . . . ?
C4 C22 C48 F1 34.9(4) . . . . ?
C4 C22 C48 F4 -84.6(4) . . . . ?
C5 C3 C4 C7 20.3(3) . . . . ?
C5 C3 C4 C22 -110.0(2) . . . . ?
C5 C3 C24 O1 177.1(2) . . . . ?
C5 C3 C24 N2 -6.9(2) . . . . ?
C7 C4 C22 N8 -139.4(2) . . . . ?
C7 C4 C22 C48 53.2(4) . . . . ?
C7 C12 C43 C46 0.1(4) . . . . ?
C7 C42 C45 C46 -0.1(4) . . . . ?
C10 N2 N5 C5 179.41(19) . . . . ?
C10 N2 C24 O1 -0.1(4) . . . . ?
C10 N2 C24 C3 -176.1(2) . . . . ?
C10 C11 C41 C36 0.2(5) . . . . ?
C11 C10 C37 C35 1.0(4) . . . . ?
C12 C7 C42 C45 -0.5(4) . . . . ?
C12 C43 C46 C45 -0.8(5) . . . . ?
C13 N4 N8 C22 170.7(2) . . . . ?
C13 N4 C3 C4 -176.2(2) . . . . ?
C13 N4 C3 C5 -50.1(3) . . . . ?
C13 N4 C3 C24 67.3(3) . . . . ?
C13 C18 C31 Cl2 178.75(18) . . . . ?
C13 C18 C31 C17 -0.7(4) . . . . ?
C17 C19 C21 C13 -1.1(4) . . . . ?
C18 C13 C21 C19 0.0(3) . . . . ?
C19 C17 C31 Cl2 -179.78(18) . . . . ?
C19 C17 C31 C18 -0.3(4) . . . . ?
C21 C13 C18 C31 0.9(3) . . . . ?
C22 C4 C7 C12 -154.8(2) . . . . ?
C22 C4 C7 C42 25.3(3) . . . . ?
C24 N2 N5 C5 -2.8(3) . . . . ?
C24 N2 C10 C11 150.6(2) . . . . ?
C24 N2 C10 C37 -30.1(3) . . . . ?
C24 C3 C4 C7 -91.9(2) . . . . ?
C24 C3 C4 C22 137.78(18) . . . . ?
C24 C3 C5 N5 5.9(2) . . . . ?
C24 C3 C5 C27 -170.3(2) . . . . ?
C31 C17 C19 Cl1 -179.64(18) . . . . ?
C31 C17 C19 C21 1.2(4) . . . . ?
C35 C36 C41 C11 0.1(5) . . . . ?
C36 C35 C37 C10 -0.7(5) . . . . ?
C37 C10 C11 C41 -0.8(4) . . . . ?
C37 C35 C36 C41 0.1(5) . . . . ?
C42 C7 C12 C43 0.6(4) . . . . ?
C42 C45 C46 C43 0.8(5) . . . . ?
N1 N3 C9 C6 2.1(2) . . . . ?
N1 N3 C9 C28 -174.6(2) . . . . ?
N1 C8 C15 C38 180.0(2) . . . . ?
N1 C8 C33 C29 -179.9(2) . . . . ?
N3 N1 C8 C15 32.4(3) . . . . ?
N3 N1 C8 C33 -147.5(2) . . . . ?
N3 N1 C26 O2 178.4(2) . . . . ?
N3 N1 C26 C6 -6.1(2) . . . . ?
N6 N7 C14 C2 -3.2(3) . . . . ?
N6 N7 C14 C44 -173.2(2) . . . . ?
N6 C6 C9 N3 -130.8(2) . . . . ?
N6 C6 C9 C28 45.7(3) . . . . ?
N6 C6 C26 O2 -53.1(3) . . . . ?
N6 C6 C26 N1 131.35(18) . . . . ?
N6 C16 C25 C32 -177.3(2) . . . . ?
N6 C16 C30 C34 177.1(2) . . . . ?
N7 N6 C6 C2 17.4(2) . . . . ?
N7 N6 C6 C9 -109.2(2) . . . . ?
N7 N6 C6 C26 133.62(19) . . . . ?
N7 N6 C16 C25 3.9(3) . . . . ?
N7 N6 C16 C30 -174.4(2) . . . . ?
N7 C14 C44 F2 136.9(3) . . . . ?
N7 C14 C44 F3 -106.6(3) . . . . ?
C1 C2 C6 N6 -147.46(19) . . . . ?
C1 C2 C6 C9 -21.9(3) . . . . ?
C1 C2 C6 C26 90.5(2) . . . . ?
C1 C2 C14 N7 140.9(2) . . . . ?
C1 C2 C14 C44 -50.3(3) . . . . ?
C1 C20 C47 C50 0.6(5) . . . . ?
C1 C40 C49 C50 -0.2(5) . . . . ?
C2 C1 C20 C47 -179.9(3) . . . . ?
C2 C1 C40 C49 179.7(2) . . . . ?
C2 C6 C9 N3 110.8(2) . . . . ?
C2 C6 C9 C28 -72.6(3) . . . . ?
C2 C6 C26 O2 59.4(3) . . . . ?
C2 C6 C26 N1 -116.11(19) . . . . ?
C2 C14 C44 F2 -31.7(4) . . . . ?
C2 C14 C44 F3 84.8(3) . . . . ?
C6 N6 N7 C14 -10.0(3) . . . . ?
C6 N6 C16 C25 -148.7(2) . . . . ?
C6 N6 C16 C30 33.0(3) . . . . ?
C6 C2 C14 N7 13.4(2) . . . . ?
C6 C2 C14 C44 -177.7(2) . . . . ?
C8 N1 N3 C9 -177.09(18) . . . . ?
C8 N1 C26 O2 -1.8(4) . . . . ?
C8 N1 C26 C6 173.74(19) . . . . ?
C8 C15 C38 C39 0.0(4) . . . . ?
C9 C6 C26 O2 -177.9(3) . . . . ?
C9 C6 C26 N1 6.5(2) . . . . ?
C14 C2 C6 N6 -16.93(19) . . . . ?
C14 C2 C6 C9 108.6(2) . . . . ?
C14 C2 C6 C26 -138.94(17) . . . . ?
C15 C8 C33 C29 0.2(4) . . . . ?
C15 C38 C39 C29 0.2(5) . . . . ?
C16 N6 N7 C14 -165.9(2) . . . . ?
C16 N6 C6 C2 171.5(2) . . . . ?
C16 N6 C6 C9 44.9(3) . . . . ?
C16 N6 C6 C26 -72.3(3) . . . . ?
C16 C25 C32 Cl4 179.82(19) . . . . ?
C16 C25 C32 C23 -0.9(4) . . . . ?
C16 C30 C34 Cl3 -178.2(2) . . . . ?
C16 C30 C34 C23 1.4(4) . . . . ?
C20 C1 C2 C6 -87.1(2) . . . . ?
C20 C1 C2 C14 153.2(2) . . . . ?
C20 C1 C40 C49 0.4(4) . . . . ?
C20 C47 C50 C49 -0.4(6) . . . . ?
C25 C16 C30 C34 -1.2(4) . . . . ?
C26 N1 N3 C9 2.7(3) . . . . ?
C26 N1 C8 C15 -147.4(2) . . . . ?
C26 N1 C8 C33 32.7(3) . . . . ?
C26 C6 C9 N3 -5.5(2) . . . . ?
C26 C6 C9 C28 171.1(2) . . . . ?
C30 C16 C25 C32 0.9(4) . . . . ?
C32 C23 C34 Cl3 178.4(2) . . . . ?
C32 C23 C34 C30 -1.2(4) . . . . ?
C33 C8 C15 C38 -0.2(4) . . . . ?
C33 C29 C39 C38 -0.2(4) . . . . ?
C34 C23 C32 Cl4 -179.7(2) . . . . ?
C34 C23 C32 C25 1.0(4) . . . . ?
C39 C29 C33 C8 0.0(4) . . . . ?
C40 C1 C2 C6 93.6(3) . . . . ?
C40 C1 C2 C14 -26.0(3) . . . . ?
C40 C1 C20 C47 -0.6(4) . . . . ?
C40 C49 C50 C47 0.2(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 2.354
_oxdiff_exptl_absorpt_empirical_full_min 0.579
####################################################################### 
# 
# 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_xray_1207_auto
_database_code_depnum_ccdc_archive 'CCDC 2253538'
loop_
_audit_author_name
_audit_author_address
'li xiao yong'
;NWNU
China
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_audit_creation_date             2021-12-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 F3 N4 O'
_chemical_formula_sum            'C25 H19 F3 N4 O'
_chemical_formula_weight         448.44
_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                   9.01840(10)
_cell_length_b                   19.8009(3)
_cell_length_c                   12.6774(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.0820(10)
_cell_angle_gamma                90
_cell_volume                     2221.62(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12915
_cell_measurement_temperature    287.3(2)
_cell_measurement_theta_max      77.1580
_cell_measurement_theta_min      4.1900
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.854
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74533
_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    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17080
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.289
_diffrn_reflns_theta_min         4.197
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      287.3(2)
_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 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     69.00 115.00   0.50    0.05    --   47.57 138.00-106.00   92
  2  ω     68.00  98.00   0.50    0.05    --  107.75 138.00-106.00   60
  3  ω    145.00 171.00   0.50    0.05    --  107.75  19.00  90.00   52
  4  ω     97.00 125.00   0.50    0.05    --  107.75  19.00  90.00   56
  5  ω     99.00 124.00   0.50    0.05    --  107.75 131.00  77.00   50
  6  ω     78.00 117.00   0.50    0.05    --   47.57 131.00  77.00   78
  7  ω    -68.00 -32.00   0.50    0.05    -- -100.00  57.00 -90.00   72
  8  ω    -98.00 -57.00   0.50    0.05    --  -47.57 138.00-106.00   82
  9  ω    -77.00 -51.00   0.50    0.05    --  -47.57 131.00  77.00   52
 10  ω    -27.00  23.00   0.50    0.05    --   47.57 -19.00  60.00  100
 11  ω    -24.00  22.00   0.50    0.05    --   47.57 -19.00   0.00   92
 12  ω    -20.00  10.00   0.50    0.05    --   47.57 -19.00 -30.00   60
 13  ω    -23.00   2.00   0.50    0.05    --   47.57 -19.00-120.00   50
 14  ω    -12.00  13.00   0.50    0.05    --   47.57 -19.00-150.00   50
 15  ω     79.00 104.00   0.50    0.05    --  107.75 -99.00   0.00   50
 16  ω     51.00  76.00   0.50    0.05    --  107.75-131.00   6.00   50
 17  ω     35.00 120.00   0.50    0.05    --  107.75-138.00-168.00  170
 18  ω     36.00  61.00   0.50    0.05    --   47.57-131.00   6.00   50
 19  ω     52.00 102.00   0.50    0.05    --  107.75 -77.00   0.00  100
 20  ω     37.00  63.00   0.50    0.05    --  107.75 -57.00  60.00   52
 21  ω     35.00  62.00   0.50    0.05    --  107.75 -57.00 150.00   54
 22  ω   -108.00 -36.00   0.50    0.05    -- -100.00 109.00 -32.35  144
 23  ω   -121.00 -64.00   0.50    0.05    -- -100.00 138.00  19.27  114
 24  ω   -100.00 -75.00   0.50    0.05    -- -100.00 138.00-106.00   50
 25  ω   -120.00 -86.00   0.50    0.05    -- -100.00 136.00-140.65   68
 26  ω    -78.00 -37.00   0.50    0.05    -- -100.00 136.00-140.65   82
 27  ω   -113.00 -85.00   0.50    0.05    -- -100.00 -57.00  90.00   56
 28  ω   -172.00-121.00   0.50    0.05    -- -100.00 -57.00  90.00  102
 29  ω   -169.00-103.00   0.50    0.05    -- -100.00 -57.00-150.00  132
 30  ω   -139.00-101.00   0.50    0.05    -- -100.00-138.00-168.00   76
;
_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      -0.1161616000
_diffrn_orient_matrix_UB_12      -0.0579821000
_diffrn_orient_matrix_UB_13      -0.0160568000
_diffrn_orient_matrix_UB_21      0.1294601000
_diffrn_orient_matrix_UB_22      -0.0518653000
_diffrn_orient_matrix_UB_23      0.0223669000
_diffrn_orient_matrix_UB_31      -0.0052254000
_diffrn_orient_matrix_UB_32      0.0019075000
_diffrn_orient_matrix_UB_33      0.1207328000
_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                3872
_reflns_number_total             4459
_reflns_odcompleteness_completeness 99.51
_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 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         0.520
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0078(10)
_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   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.085
_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)+(0.0769P)²+0.5430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1555
_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:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 0.1607(2) 0.77154(10) 0.32346(19) 0.1546(10) Uani 1 1 d . . . . .
F2 F 0.11161(17) 0.81381(14) 0.4594(2) 0.1556(9) Uani 1 1 d . . . . .
F3 F 0.20804(17) 0.87325(10) 0.3558(2) 0.1442(9) Uani 1 1 d . . . . .
O1 O 0.49559(13) 0.72963(6) 0.71085(9) 0.0551(3) Uani 1 1 d . . . . .
N1 N 0.76636(15) 0.65633(7) 0.58409(11) 0.0521(3) Uani 1 1 d . . . . .
N2 N 0.67590(15) 0.65832(7) 0.66388(11) 0.0488(3) Uani 1 1 d . . . . .
N3 N 0.59138(15) 0.81525(7) 0.54422(11) 0.0510(3) Uani 1 1 d . . . . .
N4 N 0.45007(16) 0.84122(7) 0.50670(13) 0.0577(4) Uani 1 1 d . . . . .
C25 C 0.2127(2) 0.81379(12) 0.3999(2) 0.0774(6) Uani 1 1 d . . . . .
C1 C 0.57601(16) 0.71065(8) 0.65008(12) 0.0447(3) Uani 1 1 d . . . . .
C2 C 0.58791(16) 0.74118(8) 0.54129(12) 0.0451(4) Uani 1 1 d . . . . .
C3 C 0.72240(17) 0.70398(9) 0.51685(13) 0.0486(4) Uani 1 1 d . . . . .
C4 C 0.7929(2) 0.71705(11) 0.42206(15) 0.0653(5) Uani 1 1 d . . . . .
H4A H 0.886774 0.692962 0.430091 0.098 Uiso 1 1 calc R U . . .
H4B H 0.811331 0.764569 0.416817 0.098 Uiso 1 1 calc R U . . .
H4C H 0.726100 0.702064 0.358043 0.098 Uiso 1 1 calc R U . . .
C5 C 0.44310(17) 0.72759(8) 0.45339(12) 0.0483(4) Uani 1 1 d . . . . .
H5 H 0.475095 0.725479 0.383838 0.058 Uiso 1 1 calc R U . . .
C6 C 0.36560(19) 0.79454(9) 0.45876(15) 0.0560(4) Uani 1 1 d . . . . .
C7 C 0.36108(19) 0.66250(9) 0.46650(13) 0.0515(4) Uani 1 1 d . . . . .
C8 C 0.2560(2) 0.65656(11) 0.53183(16) 0.0648(5) Uani 1 1 d . . . . .
H8 H 0.231174 0.694094 0.568986 0.078 Uiso 1 1 calc R U . . .
C9 C 0.1868(3) 0.59475(13) 0.5426(2) 0.0838(7) Uani 1 1 d . . . . .
H9 H 0.115062 0.591288 0.586120 0.101 Uiso 1 1 calc R U . . .
C10 C 0.2240(3) 0.53918(13) 0.4893(2) 0.0927(8) Uani 1 1 d . . . . .
H10 H 0.178232 0.497862 0.497020 0.111 Uiso 1 1 calc R U . . .
C11 C 0.3280(3) 0.54435(12) 0.4251(2) 0.0956(8) Uani 1 1 d . . . . .
H11 H 0.353695 0.506407 0.389231 0.115 Uiso 1 1 calc R U . . .
C12 C 0.3959(3) 0.60571(11) 0.41272(19) 0.0739(6) Uani 1 1 d . . . . .
H12 H 0.465851 0.608798 0.367723 0.089 Uiso 1 1 calc R U . . .
C13 C 0.68885(19) 0.85291(8) 0.62384(13) 0.0521(4) Uani 1 1 d . . . . .
C14 C 0.6336(2) 0.90659(10) 0.67434(17) 0.0695(5) Uani 1 1 d . . . . .
H14 H 0.530730 0.916162 0.659867 0.083 Uiso 1 1 calc R U . . .
C15 C 0.7312(3) 0.94601(12) 0.7463(2) 0.0873(7) Uani 1 1 d . . . . .
H15 H 0.693779 0.982502 0.779254 0.105 Uiso 1 1 calc R U . . .
C16 C 0.8827(3) 0.93181(12) 0.7696(2) 0.0854(7) Uani 1 1 d . . . . .
H16 H 0.948036 0.958850 0.817479 0.103 Uiso 1 1 calc R U . . .
C17 C 0.9376(2) 0.87749(13) 0.72179(19) 0.0780(6) Uani 1 1 d . . . . .
H17 H 1.039959 0.867122 0.738786 0.094 Uiso 1 1 calc R U . . .
C18 C 0.8413(2) 0.83799(10) 0.64839(17) 0.0652(5) Uani 1 1 d . . . . .
H18 H 0.879275 0.801513 0.615717 0.078 Uiso 1 1 calc R U . . .
C19 C 0.70421(19) 0.61092(8) 0.74953(12) 0.0493(4) Uani 1 1 d . . . . .
C20 C 0.5880(2) 0.59235(9) 0.80067(15) 0.0606(4) Uani 1 1 d . . . . .
H20 H 0.491935 0.610625 0.779227 0.073 Uiso 1 1 calc R U . . .
C21 C 0.6166(3) 0.54621(10) 0.88413(17) 0.0737(6) Uani 1 1 d . . . . .
H21 H 0.539468 0.534073 0.919675 0.088 Uiso 1 1 calc R U . . .
C22 C 0.7563(3) 0.51841(12) 0.91479(18) 0.0834(7) Uani 1 1 d . . . . .
H22 H 0.774120 0.487183 0.970596 0.100 Uiso 1 1 calc R U . . .
C23 C 0.8709(3) 0.53662(13) 0.8630(2) 0.0845(7) Uani 1 1 d . . . . .
H23 H 0.966003 0.517226 0.883559 0.101 Uiso 1 1 calc R U . . .
C24 C 0.8462(2) 0.58347(11) 0.78071(16) 0.0661(5) Uani 1 1 d . . . . .
H24 H 0.924467 0.596314 0.746784 0.079 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 C25 1.298(3) . ?
F2 C25 1.291(3) . ?
F3 C25 1.300(3) . ?
O1 C1 1.2147(18) . ?
N1 N2 1.4169(18) . ?
N1 C3 1.282(2) . ?
N2 C1 1.362(2) . ?
N2 C19 1.421(2) . ?
N3 N4 1.3717(19) . ?
N3 C2 1.467(2) . ?
N3 C13 1.416(2) . ?
N4 C6 1.275(2) . ?
C25 C6 1.486(3) . ?
C1 C2 1.528(2) . ?
C2 C3 1.501(2) . ?
C2 C5 1.569(2) . ?
C3 C4 1.486(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5 0.9800 . ?
C5 C6 1.506(2) . ?
C5 C7 1.511(2) . ?
C7 C8 1.378(3) . ?
C7 C12 1.382(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.366(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.359(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(3) . ?
C13 C18 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(2) . ?
C19 C24 1.377(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.361(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.375(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(3) . ?
C24 H24 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
C3 N1 N2 107.89(13) . . ?
N1 N2 C19 118.92(13) . . ?
C1 N2 N1 112.76(12) . . ?
C1 N2 C19 128.17(13) . . ?
N4 N3 C2 110.62(12) . . ?
N4 N3 C13 117.24(14) . . ?
C13 N3 C2 123.47(13) . . ?
C6 N4 N3 108.88(14) . . ?
F1 C25 F3 106.6(2) . . ?
F1 C25 C6 112.2(2) . . ?
F2 C25 F1 104.0(2) . . ?
F2 C25 F3 106.4(2) . . ?
F2 C25 C6 113.4(2) . . ?
F3 C25 C6 113.47(17) . . ?
O1 C1 N2 127.93(14) . . ?
O1 C1 C2 127.15(14) . . ?
N2 C1 C2 104.91(12) . . ?
N3 C2 C1 112.17(12) . . ?
N3 C2 C3 118.78(13) . . ?
N3 C2 C5 101.55(12) . . ?
C1 C2 C5 112.33(12) . . ?
C3 C2 C1 101.06(12) . . ?
C3 C2 C5 111.38(13) . . ?
N1 C3 C2 112.50(14) . . ?
N1 C3 C4 122.68(15) . . ?
C4 C3 C2 124.72(15) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5 107.3 . . ?
C6 C5 C2 98.46(13) . . ?
C6 C5 H5 107.3 . . ?
C6 C5 C7 120.30(14) . . ?
C7 C5 C2 115.25(13) . . ?
C7 C5 H5 107.3 . . ?
N4 C6 C25 117.72(17) . . ?
N4 C6 C5 114.81(15) . . ?
C25 C6 C5 126.65(17) . . ?
C8 C7 C5 123.12(16) . . ?
C8 C7 C12 118.36(18) . . ?
C12 C7 C5 118.50(17) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.7(2) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 N3 120.35(16) . . ?
C14 C13 C18 119.45(17) . . ?
C18 C13 N3 120.15(16) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 119.9(2) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 N2 119.51(15) . . ?
C24 C19 N2 120.05(16) . . ?
C24 C19 C20 120.44(17) . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.15(19) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.8(2) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 119.2(2) . . ?
C19 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?

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 C25 C6 N4 155.3(2) . . . . ?
F1 C25 C6 C5 -13.7(3) . . . . ?
F2 C25 C6 N4 -87.2(3) . . . . ?
F2 C25 C6 C5 103.8(3) . . . . ?
F3 C25 C6 N4 34.4(3) . . . . ?
F3 C25 C6 C5 -134.6(2) . . . . ?
O1 C1 C2 N3 42.9(2) . . . . ?
O1 C1 C2 C3 170.44(16) . . . . ?
O1 C1 C2 C5 -70.8(2) . . . . ?
N1 N2 C1 O1 -171.57(15) . . . . ?
N1 N2 C1 C2 7.87(17) . . . . ?
N1 N2 C19 C20 -153.32(15) . . . . ?
N1 N2 C19 C24 26.3(2) . . . . ?
N2 N1 C3 C2 -3.68(18) . . . . ?
N2 N1 C3 C4 179.86(15) . . . . ?
N2 C1 C2 N3 -136.56(13) . . . . ?
N2 C1 C2 C3 -9.01(15) . . . . ?
N2 C1 C2 C5 109.79(14) . . . . ?
N2 C19 C20 C21 -179.91(16) . . . . ?
N2 C19 C24 C23 -178.94(18) . . . . ?
N3 N4 C6 C25 -172.44(17) . . . . ?
N3 N4 C6 C5 -2.1(2) . . . . ?
N3 C2 C3 N1 131.08(15) . . . . ?
N3 C2 C3 C4 -52.5(2) . . . . ?
N3 C2 C5 C6 -21.36(14) . . . . ?
N3 C2 C5 C7 -150.72(14) . . . . ?
N3 C13 C14 C15 -175.41(19) . . . . ?
N3 C13 C18 C17 176.23(18) . . . . ?
N4 N3 C2 C1 -97.06(15) . . . . ?
N4 N3 C2 C3 145.54(14) . . . . ?
N4 N3 C2 C5 23.07(16) . . . . ?
N4 N3 C13 C14 11.3(2) . . . . ?
N4 N3 C13 C18 -166.02(16) . . . . ?
C1 N2 C19 C20 31.4(2) . . . . ?
C1 N2 C19 C24 -148.97(18) . . . . ?
C1 C2 C3 N1 7.98(17) . . . . ?
C1 C2 C3 C4 -175.64(16) . . . . ?
C1 C2 C5 C6 98.66(15) . . . . ?
C1 C2 C5 C7 -30.70(19) . . . . ?
C2 N3 N4 C6 -14.24(19) . . . . ?
C2 N3 C13 C14 -133.32(18) . . . . ?
C2 N3 C13 C18 49.4(2) . . . . ?
C2 C5 C6 N4 15.72(19) . . . . ?
C2 C5 C6 C25 -174.99(18) . . . . ?
C2 C5 C7 C8 84.6(2) . . . . ?
C2 C5 C7 C12 -93.54(19) . . . . ?
C3 N1 N2 C1 -2.96(18) . . . . ?
C3 N1 N2 C19 -178.90(14) . . . . ?
C3 C2 C5 C6 -148.79(14) . . . . ?
C3 C2 C5 C7 81.85(17) . . . . ?
C5 C2 C3 N1 -111.50(16) . . . . ?
C5 C2 C3 C4 64.9(2) . . . . ?
C5 C7 C8 C9 -178.45(18) . . . . ?
C5 C7 C12 C11 177.7(2) . . . . ?
C6 C5 C7 C8 -33.0(2) . . . . ?
C6 C5 C7 C12 148.80(18) . . . . ?
C7 C5 C6 N4 141.63(16) . . . . ?
C7 C5 C6 C25 -49.1(3) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C8 C7 C12 C11 -0.6(3) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C7 1.0(4) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
C13 N3 N4 C6 -163.14(15) . . . . ?
C13 N3 C2 C1 49.53(19) . . . . ?
C13 N3 C2 C3 -67.9(2) . . . . ?
C13 N3 C2 C5 169.66(14) . . . . ?
C13 C14 C15 C16 -1.0(4) . . . . ?
C14 C13 C18 C17 -1.1(3) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C16 C17 C18 1.5(4) . . . . ?
C16 C17 C18 C13 -0.7(3) . . . . ?
C18 C13 C14 C15 1.9(3) . . . . ?
C19 N2 C1 O1 3.9(3) . . . . ?
C19 N2 C1 C2 -176.66(14) . . . . ?
C19 C20 C21 C22 -1.1(3) . . . . ?
C20 C19 C24 C23 0.6(3) . . . . ?
C20 C21 C22 C23 0.5(4) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 C19 -1.2(4) . . . . ?
C24 C19 C20 C21 0.5(3) . . . . ?


_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 2.203
_oxdiff_exptl_absorpt_empirical_full_min 0.392
