# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_ly616
_database_code_depnum_ccdc_archive 'CCDC 2502688'
loop_
_audit_author_name
_audit_author_address
Yang
;Guangzhou Medical University
China
;
_audit_update_record             
;
2025-11-13 deposited with the CCDC.	2026-05-11 downloaded from the CCDC.
;
_audit_creation_date             2025-05-26
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31.078 H23.078 Cl F N2 O P'
_chemical_formula_sum            'C33 H25 Cl F N2 O P'
_chemical_formula_weight         550.97
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N P F'
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'
P P 0.2955 0.4335 '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      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   10.87240(10)
_cell_length_b                   10.87240(10)
_cell_length_c                   48.5753(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5742.04(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    31716
_cell_measurement_temperature    291.8(7)
_cell_measurement_theta_max      74.2730
_cell_measurement_theta_min      3.5980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.986
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            64723
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.145
_diffrn_reflns_theta_min         3.640
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.8(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00 -35.00   0.25    0.10    -- -103.00  77.00  90.00  140
  2  ω      7.00  33.00   0.25    0.05    --  -43.18  38.00  30.00  104
  3  ω    -60.00 -34.00   0.25    0.10    -- -103.00  77.00 -30.00  104
  4  ω      1.00  26.00   0.25    0.05    --  -43.18  38.00-120.00  100
  5  ω     -5.00  64.00   0.25    0.05    --   43.18 -77.00  30.00  276
  6  ω    -17.00  48.00   0.25    0.05    --   43.18 -57.00 120.00  260
  7  ω    -27.00   9.00   0.25    0.05    --   43.18 -38.00  90.00  144
  8  ω    -16.00  51.00   0.25    0.05    --   43.18 -77.00-120.00  268
  9  ω    -32.00  13.00   0.25    0.05    --   43.18 -38.00-180.00  180
 10  ω     36.00  86.00   0.25    0.10    --  107.57 -95.00 -90.00  200
 11  ω     38.00  81.00   0.25    0.10    --  107.57-126.00 -90.00  172
 12  ω     36.00  83.00   0.25    0.10    --  107.57-126.00  30.00  188
 13  ω      0.00  76.00   0.25    0.05    --   43.18 -99.00   0.00  304
 14  ω     47.00  75.00   0.25    0.10    --  107.57 -77.00 -90.00  112
 15  ω     40.00  78.00   0.25    0.10    --  107.57 -77.00-120.00  152
 16  ω     41.00  66.00   0.25    0.10    --  107.57 -77.00  30.00  100
 17  ω     93.00 118.00   0.25    0.10    --  107.57  15.00 150.00  100
 18  ω     94.00 139.00   0.25    0.10    --  107.57  15.00 120.00  180
 19  ω     95.00 172.00   0.25    0.10    --  107.57  45.00  30.00  308
 20  ω    104.00 138.00   0.25    0.10    --  107.57  15.00  30.00  136
 21  ω     94.00 137.00   0.25    0.10    --  107.57  15.00   0.00  172
 22  ω   -157.00 -90.00   0.25    0.10    -- -103.00 -30.00 -90.00  268
 23  ω   -126.00 -90.00   0.25    0.10    -- -103.00 -15.00-180.00  144
 24  ω   -132.00 -93.00   0.25    0.10    -- -103.00 -15.00 -90.00  156
 25  ω   -129.00-104.00   0.25    0.10    -- -103.00 -15.00   0.00  100
 26  ω   -133.00 -96.00   0.25    0.10    -- -103.00 -15.00  30.00  148
 27  ω   -133.00 -91.00   0.25    0.10    -- -103.00 -15.00 120.00  168
 28  ω   -132.00 -88.00   0.25    0.10    -- -103.00 -15.00 150.00  176
 29  ω   -115.00 -29.00   0.25    0.05    --  -43.18 -19.00  90.00  344
 30  ω    -92.00 -41.00   0.25    0.10    -- -103.00  95.00 142.95  204
 31  ω    -97.00 -41.00   0.25    0.10    -- -103.00 114.00 149.19  224
 32  ω    -97.00 -46.00   0.25    0.10    -- -103.00 114.00 173.69  204
 33  ω    -93.00 -68.00   0.25    0.10    -- -103.00 102.00 150.72  100
 34  ω    -97.00 -39.00   0.25    0.10    -- -103.00 114.00  11.83  232
 35  ω    -57.00 -32.00   0.25    0.10    -- -103.00 102.00  -0.65  100
 36  ω    -93.00 -68.00   0.25    0.10    -- -103.00 102.00  -0.65  100
 37  ω    -92.00 -66.00   0.25    0.10    -- -103.00 101.00  66.15  104
 38  ω    -65.00 -31.00   0.25    0.10    -- -103.00 102.00 109.47  136
 39  ω    -54.00 -29.00   0.25    0.10    -- -103.00 101.00 -35.16  100
 40  ω    -92.00 -60.00   0.25    0.10    -- -103.00 101.00 -35.16  128
 41  ω    -93.00 -68.00   0.25    0.10    -- -103.00 102.00 -65.36  100
 42  ω    -57.00 -32.00   0.25    0.10    -- -103.00 126.00-180.00  100
 43  ω   -101.00 -76.00   0.25    0.10    -- -103.00 126.00-180.00  100
 44  ω    -92.00 -54.00   0.25    0.10    -- -103.00  97.00-140.02  152
 45  ω    -92.00 -38.00   0.25    0.10    -- -103.00  97.00  95.94  216
;
_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      0.0423663000
_diffrn_orient_matrix_UB_12      -0.0746679000
_diffrn_orient_matrix_UB_13      -0.0252372000
_diffrn_orient_matrix_UB_21      0.0097210000
_diffrn_orient_matrix_UB_22      0.1194532000
_diffrn_orient_matrix_UB_23      -0.0169062000
_diffrn_orient_matrix_UB_31      0.1348838000
_diffrn_orient_matrix_UB_32      0.0148511000
_diffrn_orient_matrix_UB_33      0.0091354000
_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         0.665
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                5487
_reflns_number_total             5839
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.026
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 
;
 Flack x determined using 2093 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         5839
_refine_ls_number_restraints     309
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0924
_refine_ls_restrained_S_all      1.197
_refine_ls_shift/su_max          6.234
_refine_ls_shift/su_mean         0.273
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1955P)²+0.7992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2813
_refine_ls_wR_factor_ref         0.2860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C13) = Uanis(C17) = Uanis(C18) = Uanis(C16) = Uanis(C15) = Uanis(C14) =
Uanis(C12)
3. Rigid body (RIGU) restrains
 C13, C14, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.009
 C12, C13, C14, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.009
 C12, Cl1, C26, C25, C27, C24, H25, H27, C28, C23, C29, N1, C22, H23, N2, P1,
 C8, C21, H22, O1, C1, C35, C7, C9, H21, C2, C6, C30, C34, H7, H9, C10, H2, C3,
 C5, H30, C31, C33, H34, F1, C11, H3, C4, H5, H31, C32, H33, H11A, H11B, H4,
 H32, H12A, H12B, C13, C17, C14, H17, C18, C15, H14, H18, C16, H15, H16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.009
4. Others
 Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C16)=Sof(H16)=Sof(C15)=Sof(H15)=
 Sof(C14)=Sof(H14)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C17(H17), C18(H18), C16(H16),
 C15(H15), C14(H14), C21(H21), C22(H22), C23(H23), C25(H25), C27(H27), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34)
5.c Fitted hexagon refined as free rotating group:
 C17(C18,C16,C15,C14,C13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.0758(2) 0.2606(3) 0.32040(4) 0.1204(8) Uani 1 1 d . . . . .
P1 P 0.11595(12) -0.02593(11) 0.41630(3) 0.0673(4) Uani 1 1 d . . . . .
F1 F 0.1879(7) 0.3853(4) 0.47902(10) 0.142(2) Uani 1 1 d . . . . .
O1 O 0.2215(4) -0.0773(4) 0.40153(10) 0.0872(11) Uani 1 1 d . . . . .
N1 N 0.1192(4) 0.1273(4) 0.42095(9) 0.0684(9) Uani 1 1 d . . . . .
N2 N -0.0390(6) 0.3116(5) 0.43812(12) 0.0878(13) Uani 1 1 d . . . . .
C1 C 0.1027(5) -0.0779(4) 0.45086(11) 0.0702(11) Uani 1 1 d . . . . .
C2 C 0.0495(7) -0.1908(5) 0.45692(15) 0.0858(14) Uani 1 1 d . . . . .
H2 H 0.012888 -0.236452 0.442958 0.103 Uiso 1 1 calc R U . . .
C3 C 0.0506(9) -0.2358(6) 0.48335(16) 0.100(2) Uani 1 1 d . . . . .
H3 H 0.009173 -0.308079 0.487656 0.120 Uiso 1 1 calc R U . . .
C4 C 0.1143(8) -0.1718(6) 0.50352(15) 0.0948(17) Uani 1 1 d . . . . .
H4 H 0.122261 -0.205855 0.520992 0.114 Uiso 1 1 calc R U . . .
C5 C 0.1657(7) -0.0594(5) 0.49812(13) 0.0829(14) Uani 1 1 d . . . . .
H5 H 0.203672 -0.015871 0.512235 0.100 Uiso 1 1 calc R U . . .
C6 C 0.1618(5) -0.0093(5) 0.47159(11) 0.0696(10) Uani 1 1 d . . . . .
C7 C 0.2138(5) 0.1098(5) 0.46543(11) 0.0715(11) Uani 1 1 d . . . . .
H7 H 0.267128 0.143475 0.478366 0.086 Uiso 1 1 calc R U . . .
C8 C 0.1923(5) 0.1748(5) 0.44312(11) 0.0680(10) Uani 1 1 d . . . . .
C9 C 0.2445(6) 0.2971(5) 0.43753(12) 0.0746(12) Uani 1 1 d . . . . .
H9 H 0.280946 0.307596 0.420369 0.090 Uiso 1 1 calc R U . . .
C10 C 0.2457(7) 0.3916(6) 0.45364(13) 0.0880(15) Uani 1 1 d . . . . .
C11 C 0.3017(8) 0.5145(7) 0.44960(16) 0.0983(18) Uani 1 1 d . . . . .
H11A H 0.338997 0.517084 0.431473 0.118 Uiso 1 1 calc R U . . .
H11B H 0.236861 0.575761 0.449995 0.118 Uiso 1 1 calc R U . . .
C12 C 0.3948(9) 0.5478(7) 0.4700(2) 0.1109(13) Uani 1 1 d . . . . .
H12A H 0.454725 0.481739 0.470619 0.133 Uiso 1 1 calc R U . . .
H12B H 0.354752 0.549806 0.487880 0.133 Uiso 1 1 calc R U . . .
C17 C 0.5924(6) 0.6652(5) 0.46912(18) 0.1109(13) Uani 0.616(10) 1 d G . P A 1
H17 H 0.632455 0.591148 0.472500 0.133 Uiso 0.616(10) 1 calc R U P A 1
C18 C 0.6598(5) 0.7732(7) 0.46648(19) 0.1109(13) Uani 0.616(10) 1 d G . P A 1
H18 H 0.745016 0.771363 0.468106 0.133 Uiso 0.616(10) 1 calc R U P A 1
C16 C 0.5999(7) 0.8838(5) 0.46143(19) 0.1109(13) Uani 0.616(10) 1 d G . P A 1
H16 H 0.645009 0.956049 0.459665 0.133 Uiso 0.616(10) 1 calc R U P A 1
C15 C 0.4725(7) 0.8865(5) 0.4590(2) 0.1109(13) Uani 0.616(10) 1 d G . P A 1
H15 H 0.432441 0.960521 0.455617 0.133 Uiso 0.616(10) 1 calc R U P A 1
C14 C 0.4051(5) 0.7785(6) 0.46163(18) 0.1109(13) Uani 0.616(10) 1 d G . P A 1
H14 H 0.319877 0.780308 0.460010 0.133 Uiso 0.616(10) 1 calc R U P A 1
C13 C 0.4650(6) 0.6679(5) 0.46669(16) 0.1109(13) Uani 1 1 d G . . . .
C21 C -0.1067(9) 0.4051(7) 0.4465(2) 0.107(2) Uani 1 1 d . . . . .
H21 H -0.127751 0.409627 0.465043 0.128 Uiso 1 1 calc R U . . .
C22 C -0.1490(10) 0.4989(8) 0.4286(2) 0.117(2) Uani 1 1 d . . . . .
H22 H -0.191124 0.566278 0.435631 0.141 Uiso 1 1 calc R U . . .
C23 C -0.1285(7) 0.4907(7) 0.40183(18) 0.0996(18) Uani 1 1 d . . . . .
H23 H -0.159888 0.550159 0.389999 0.120 Uiso 1 1 calc R U . . .
C24 C -0.0584(5) 0.3909(5) 0.39107(15) 0.0809(12) Uani 1 1 d . . . . .
C25 C -0.0352(6) 0.3734(6) 0.36331(15) 0.0873(14) Uani 1 1 d . . . . .
H25 H -0.069314 0.426367 0.350357 0.105 Uiso 1 1 calc R U . . .
C26 C 0.0375(7) 0.2788(7) 0.35504(14) 0.0874(15) Uani 1 1 d . . . . .
C27 C 0.0932(5) 0.1984(5) 0.37400(12) 0.0746(11) Uani 1 1 d . . . . .
H27 H 0.147184 0.137912 0.367931 0.090 Uiso 1 1 calc R U . . .
C28 C 0.0674(5) 0.2098(5) 0.40125(11) 0.0689(10) Uani 1 1 d . . . . .
C29 C -0.0113(5) 0.3063(5) 0.41065(12) 0.0724(11) Uani 1 1 d . . . . .
C30 C -0.1378(7) -0.0064(9) 0.4083(2) 0.108(2) Uani 1 1 d . . . . .
H30 H -0.139654 0.049037 0.422860 0.129 Uiso 1 1 calc R U . . .
C31 C -0.2449(9) -0.0401(11) 0.3949(2) 0.129(3) Uani 1 1 d . . . . .
H31 H -0.319900 -0.006657 0.400339 0.155 Uiso 1 1 calc R U . . .
C32 C -0.2400(10) -0.1252(10) 0.3731(2) 0.129(3) Uani 1 1 d . . . . .
H32 H -0.312322 -0.148580 0.364365 0.155 Uiso 1 1 calc R U . . .
C33 C -0.1304(11) -0.1743(8) 0.36465(17) 0.115(2) Uani 1 1 d . . . . .
H33 H -0.128094 -0.230382 0.350212 0.138 Uiso 1 1 calc R U . . .
C34 C -0.0258(8) -0.1401(5) 0.37752(12) 0.0893(16) Uani 1 1 d . . . . .
H34 H 0.048830 -0.172582 0.371644 0.107 Uiso 1 1 calc R U . . .
C35 C -0.0271(6) -0.0572(5) 0.39943(12) 0.0772(12) Uani 1 1 d . . . . .


_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 C26 1.745(7) . ?
P1 O1 1.464(4) . ?
P1 N1 1.682(4) . ?
P1 C1 1.777(6) . ?
P1 C35 1.790(6) . ?
F1 C10 1.385(8) . ?
N1 C8 1.434(6) . ?
N1 C28 1.427(7) . ?
N2 C21 1.320(9) . ?
N2 C29 1.369(8) . ?
C1 C2 1.388(8) . ?
C1 C6 1.408(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(8) . ?
C6 C7 1.445(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.314(8) . ?
C8 C9 1.471(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.292(9) . ?
C10 C11 1.481(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.464(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.521(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.3900 . ?
C17 C13 1.3900 . ?
C18 H18 0.9300 . ?
C18 C16 1.3900 . ?
C16 H16 0.9300 . ?
C16 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C14 H14 0.9300 . ?
C14 C13 1.3900 . ?
C21 H21 0.9300 . ?
C21 C22 1.418(13) . ?
C22 H22 0.9300 . ?
C22 C23 1.320(12) . ?
C23 H23 0.9300 . ?
C23 C24 1.425(9) . ?
C24 C25 1.385(10) . ?
C24 C29 1.419(8) . ?
C25 H25 0.9300 . ?
C25 C26 1.358(10) . ?
C26 C27 1.407(8) . ?
C27 H27 0.9300 . ?
C27 C28 1.358(8) . ?
C28 C29 1.429(7) . ?
C30 H30 0.9300 . ?
C30 C31 1.382(11) . ?
C30 C35 1.393(11) . ?
C31 H31 0.9300 . ?
C31 C32 1.408(16) . ?
C32 H32 0.9300 . ?
C32 C33 1.368(16) . ?
C33 H33 0.9300 . ?
C33 C34 1.350(12) . ?
C34 H34 0.9300 . ?
C34 C35 1.395(8) . ?

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
O1 P1 N1 115.3(3) . . ?
O1 P1 C1 113.9(3) . . ?
O1 P1 C35 112.6(3) . . ?
N1 P1 C1 101.0(2) . . ?
N1 P1 C35 105.5(2) . . ?
C1 P1 C35 107.5(3) . . ?
C8 N1 P1 118.0(3) . . ?
C8 N1 C28 119.8(4) . . ?
C28 N1 P1 121.6(3) . . ?
C21 N2 C29 117.2(6) . . ?
C2 C1 P1 121.0(4) . . ?
C2 C1 C6 120.4(5) . . ?
C6 C1 P1 118.0(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.1(6) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(7) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(6) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 120.3(5) . . ?
C5 C6 C1 117.8(5) . . ?
C5 C6 C7 121.9(5) . . ?
C6 C7 H7 117.2 . . ?
C8 C7 C6 125.7(5) . . ?
C8 C7 H7 117.2 . . ?
N1 C8 C9 113.6(5) . . ?
C7 C8 N1 121.6(5) . . ?
C7 C8 C9 124.7(5) . . ?
C8 C9 H9 116.2 . . ?
C10 C9 C8 127.7(6) . . ?
C10 C9 H9 116.1 . . ?
F1 C10 C11 110.4(6) . . ?
C9 C10 F1 119.7(6) . . ?
C9 C10 C11 129.9(7) . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 C10 114.7(7) . . ?
C12 C11 H11A 108.2 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 107.9 . . ?
C11 C12 H12B 107.3 . . ?
C11 C12 C13 119.1(7) . . ?
H12A C12 H12B 107.1 . . ?
C13 C12 H12A 107.8 . . ?
C13 C12 H12B 107.0 . . ?
C18 C17 H17 120.2 . . ?
C18 C17 C13 120.0 . . ?
C13 C17 H17 119.8 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C16 120.0 . . ?
C16 C18 H18 120.0 . . ?
C18 C16 H16 120.0 . . ?
C15 C16 C18 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C17 C13 C12 118.2(6) . . ?
C14 C13 C12 121.8(6) . . ?
C14 C13 C17 120.0 . . ?
N2 C21 H21 118.4 . . ?
N2 C21 C22 123.0(8) . . ?
C22 C21 H21 118.6 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.1(7) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 120.1(7) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C29 116.2(6) . . ?
C25 C24 C23 124.0(6) . . ?
C25 C24 C29 119.9(6) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.9(6) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 Cl1 120.7(5) . . ?
C25 C26 C27 121.8(6) . . ?
C27 C26 Cl1 117.3(5) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 C26 119.5(6) . . ?
C28 C27 H27 120.2 . . ?
C27 C28 N1 121.0(5) . . ?
C27 C28 C29 120.1(5) . . ?
C29 C28 N1 118.9(5) . . ?
N2 C29 C24 123.1(5) . . ?
N2 C29 C28 118.3(5) . . ?
C24 C29 C28 118.5(6) . . ?
C31 C30 H30 120.5 . . ?
C31 C30 C35 118.6(9) . . ?
C35 C30 H30 120.9 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.6(10) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 H32 119.3 . . ?
C31 C32 C33 121.1(8) . . ?
C33 C32 H32 119.6 . . ?
C32 C33 H33 120.3 . . ?
C34 C33 C32 119.1(8) . . ?
C34 C33 H33 120.6 . . ?
C33 C34 H34 119.2 . . ?
C33 C34 C35 121.5(9) . . ?
C35 C34 H34 119.3 . . ?
C30 C35 P1 122.3(5) . . ?
C34 C35 P1 117.6(6) . . ?
C34 C35 C30 120.0(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C26 C27 C28 179.3(5) . . . . ?
P1 N1 C8 C7 -28.1(7) . . . . ?
P1 N1 C8 C9 148.7(4) . . . . ?
P1 N1 C28 C27 -48.3(7) . . . . ?
P1 N1 C28 C29 132.6(4) . . . . ?
P1 C1 C2 C3 173.5(6) . . . . ?
P1 C1 C6 C5 -171.3(5) . . . . ?
P1 C1 C6 C7 10.0(7) . . . . ?
F1 C10 C11 C12 60.2(10) . . . . ?
O1 P1 N1 C8 -80.7(5) . . . . ?
O1 P1 N1 C28 89.8(5) . . . . ?
O1 P1 C1 C2 -81.5(6) . . . . ?
O1 P1 C1 C6 90.3(5) . . . . ?
O1 P1 C35 C30 -173.2(6) . . . . ?
O1 P1 C35 C34 9.8(6) . . . . ?
N1 P1 C1 C2 154.4(5) . . . . ?
N1 P1 C1 C6 -33.8(5) . . . . ?
N1 P1 C35 C30 -46.6(7) . . . . ?
N1 P1 C35 C34 136.4(5) . . . . ?
N1 C8 C9 C10 133.8(7) . . . . ?
N1 C28 C29 N2 -3.5(8) . . . . ?
N1 C28 C29 C24 177.4(5) . . . . ?
N2 C21 C22 C23 4.9(16) . . . . ?
C1 P1 N1 C8 42.5(4) . . . . ?
C1 P1 N1 C28 -147.0(4) . . . . ?
C1 P1 C35 C30 60.5(7) . . . . ?
C1 P1 C35 C34 -116.4(5) . . . . ?
C1 C2 C3 C4 -5.3(12) . . . . ?
C1 C6 C7 C8 13.9(9) . . . . ?
C2 C1 C6 C5 0.6(8) . . . . ?
C2 C1 C6 C7 -178.2(6) . . . . ?
C2 C3 C4 C5 6.3(13) . . . . ?
C3 C4 C5 C6 -3.9(12) . . . . ?
C4 C5 C6 C1 0.4(9) . . . . ?
C4 C5 C6 C7 179.1(6) . . . . ?
C5 C6 C7 C8 -164.8(6) . . . . ?
C6 C1 C2 C3 1.9(10) . . . . ?
C6 C7 C8 N1 -4.9(9) . . . . ?
C6 C7 C8 C9 178.7(5) . . . . ?
C7 C8 C9 C10 -49.6(10) . . . . ?
C8 N1 C28 C27 122.0(6) . . . . ?
C8 N1 C28 C29 -57.1(7) . . . . ?
C8 C9 C10 F1 -3.2(12) . . . . ?
C8 C9 C10 C11 176.8(7) . . . . ?
C9 C10 C11 C12 -119.8(10) . . . . ?
C10 C11 C12 C13 175.6(8) . . . . ?
C11 C12 C13 C17 -131.6(8) . . . . ?
C11 C12 C13 C14 49.1(12) . . . . ?
C17 C18 C16 C15 0.0 . . . . ?
C18 C17 C13 C12 -179.3(8) . . . . ?
C18 C17 C13 C14 0.0 . . . . ?
C18 C16 C15 C14 0.0 . . . . ?
C16 C15 C14 C13 0.0 . . . . ?
C15 C14 C13 C12 179.3(8) . . . . ?
C15 C14 C13 C17 0.0 . . . . ?
C13 C17 C18 C16 0.0 . . . . ?
C21 N2 C29 C24 -4.3(10) . . . . ?
C21 N2 C29 C28 176.7(7) . . . . ?
C21 C22 C23 C24 -3.3(14) . . . . ?
C22 C23 C24 C25 178.3(9) . . . . ?
C22 C23 C24 C29 -1.6(11) . . . . ?
C23 C24 C25 C26 176.9(7) . . . . ?
C23 C24 C29 N2 5.6(9) . . . . ?
C23 C24 C29 C28 -175.3(6) . . . . ?
C24 C25 C26 Cl1 -176.0(5) . . . . ?
C24 C25 C26 C27 -1.5(11) . . . . ?
C25 C24 C29 N2 -174.3(6) . . . . ?
C25 C24 C29 C28 4.8(8) . . . . ?
C25 C26 C27 C28 4.6(10) . . . . ?
C26 C27 C28 N1 178.0(5) . . . . ?
C26 C27 C28 C29 -2.8(9) . . . . ?
C27 C28 C29 N2 177.4(5) . . . . ?
C27 C28 C29 C24 -1.7(8) . . . . ?
C28 N1 C8 C7 161.3(5) . . . . ?
C28 N1 C8 C9 -22.0(7) . . . . ?
C29 N2 C21 C22 -1.1(13) . . . . ?
C29 C24 C25 C26 -3.2(10) . . . . ?
C30 C31 C32 C33 -0.9(16) . . . . ?
C31 C30 C35 P1 -176.8(8) . . . . ?
C31 C30 C35 C34 0.1(13) . . . . ?
C31 C32 C33 C34 0.1(14) . . . . ?
C32 C33 C34 C35 0.7(12) . . . . ?
C33 C34 C35 P1 176.2(6) . . . . ?
C33 C34 C35 C30 -0.8(10) . . . . ?
C35 P1 N1 C8 154.4(4) . . . . ?
C35 P1 N1 C28 -35.1(5) . . . . ?
C35 P1 C1 C2 44.0(6) . . . . ?
C35 P1 C1 C6 -144.2(4) . . . . ?
C35 C30 C31 C32 0.8(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.284
_oxdiff_exptl_absorpt_empirical_full_min 0.728
####################################################################### 
# 
# 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_802_1
_database_code_depnum_ccdc_archive 'CCDC 2502352'
loop_
_audit_author_name
_audit_author_address
'Jiating Cai'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2025-11-12 deposited with the CCDC.	2026-05-11 downloaded from the CCDC.
;
_audit_creation_date             2025-04-12
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 F N3 O'
_chemical_formula_sum            'C26 H20 F N3 O'
_chemical_formula_weight         409.45
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.03310(13)
_cell_length_b                   15.5907(3)
_cell_length_c                   25.3876(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1992.15(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7376
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7330
_cell_measurement_theta_min      3.2760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12141
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.057
_diffrn_reflns_theta_min         3.327
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00   9.00   0.50    0.05    --   43.18 -38.00 150.00   86
  2  ω    -33.00  27.00   0.50    0.05    --   43.18 -42.00  78.00  120
  3  ω     38.00  68.00   0.50    0.12    --  107.57 -77.00 120.00   60
  4  ω     38.00  76.00   0.50    0.12    --  107.57 -77.00  90.00   76
  5  ω     44.00  70.00   0.50    0.12    --  107.57 -77.00  30.00   52
  6  ω     94.00 131.00   0.50    0.12    --  107.57  15.00 -30.00   74
  7  ω    108.00 134.00   0.50    0.12    --  107.57  77.00-120.00   52
  8  ω    145.00 170.00   0.50    0.12    --  107.57  77.00-120.00   50
  9  ω    113.00 175.00   0.50    0.12    --  107.57  42.00-129.00  124
 10  ω     94.00 130.00   0.50    0.12    --  107.57  15.00-120.00   72
 11  ω     58.00 120.00   0.50    0.05    --   43.18  42.00-129.00  124
 12  ω     -8.00  22.00   0.50    0.05    --  -43.18  38.00   0.00   60
 13  ω    -15.00  33.00   0.50    0.05    --  -43.18  38.00 -30.00   96
 14  ω     35.00  91.00   0.50    0.12    --  107.57 -95.00-180.00  112
 15  ω     36.00  61.00   0.50    0.12    --  107.57 -95.00  30.00   50
 16  ω    -17.00  33.00   0.50    0.05    --  -43.18  42.00-129.00  100
 17  ω    -14.00  13.00   0.50    0.05    --  -43.18  38.00-150.00   54
 18  ω    -72.00 -33.00   0.50    0.12    -- -103.00  77.00 -30.00   78
 19  ω    -68.00 -39.00   0.50    0.12    -- -103.00  77.00   0.00   58
 20  ω    -69.00 -37.00   0.50    0.12    -- -103.00  77.00  60.00   64
 21  ω    -61.00 -33.00   0.50    0.12    -- -103.00  77.00-150.00   56
 22  ω   -128.00 -93.00   0.50    0.12    -- -103.00 -15.00 -60.00   70
 23  ω   -134.00-100.00   0.50    0.12    -- -103.00 -77.00  30.00   68
 24  ω   -169.00-137.00   0.50    0.12    -- -103.00 -77.00  30.00   64
 25  ω   -174.00-148.00   0.50    0.12    -- -103.00 -42.00  78.00   52
 26  ω   -132.00-105.00   0.50    0.12    -- -103.00 -15.00 120.00   54
 27  ω   -133.00 -90.00   0.50    0.12    -- -103.00 -15.00   0.00   86
 28  ω   -113.00 -88.00   0.50    0.12    -- -103.00 -15.00 -30.00   50
 29  ω    -75.00 -31.00   0.50    0.05    --  -43.18 -42.00  78.00   88
;
_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      0.1448983000
_diffrn_orient_matrix_UB_12      -0.0802142000
_diffrn_orient_matrix_UB_13      0.0206827000
_diffrn_orient_matrix_UB_21      -0.0718727000
_diffrn_orient_matrix_UB_22      -0.0483777000
_diffrn_orient_matrix_UB_23      -0.0509825000
_diffrn_orient_matrix_UB_31      0.2599041000
_diffrn_orient_matrix_UB_32      0.0314318000
_diffrn_orient_matrix_UB_33      -0.0255905000
_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         0.641
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                3555
_reflns_number_total             3793
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1354 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3793
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.041
_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)+(0.0434P)²+0.3338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9461(3) 0.54389(7) 0.30022(4) 0.0291(3) Uani 1 1 d . . . . .
O1 O 0.5341(3) 0.16655(8) 0.23860(5) 0.0271(3) Uani 1 1 d . . . . .
N1 N 0.7612(3) 0.28425(10) 0.26662(6) 0.0207(3) Uani 1 1 d . . . . .
N2 N 0.8453(3) 0.23630(10) 0.30955(6) 0.0213(3) Uani 1 1 d . . . . .
N3 N 0.5130(3) 0.28651(10) 0.37007(6) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.4483(4) 0.29951(12) 0.19535(7) 0.0229(4) Uani 1 1 d . . . . .
C2 C 0.2521(4) 0.26502(14) 0.16223(7) 0.0278(4) Uani 1 1 d . . . . .
H2 H 0.209259 0.205757 0.164159 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1220(4) 0.31732(15) 0.12696(8) 0.0314(5) Uani 1 1 d . . . . .
H3 H -0.010534 0.294046 0.104482 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1842(4) 0.40426(15) 0.12413(8) 0.0295(5) Uani 1 1 d . . . . .
H4 H 0.094217 0.439845 0.099537 0.035 Uiso 1 1 calc R U . . .
C5 C 0.3756(4) 0.43929(14) 0.15678(7) 0.0264(4) Uani 1 1 d . . . . .
H5 H 0.416056 0.498691 0.154541 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5106(4) 0.38719(12) 0.19334(6) 0.0227(4) Uani 1 1 d . . . . .
C7 C 0.7100(4) 0.42131(12) 0.22790(7) 0.0224(4) Uani 1 1 d . . . . .
H7 H 0.755875 0.480269 0.225369 0.027 Uiso 1 1 calc R U . . .
C8 C 0.8339(4) 0.37173(11) 0.26390(7) 0.0197(4) Uani 1 1 d . . . . .
C9 C 1.0495(4) 0.39827(12) 0.29893(7) 0.0208(4) Uani 1 1 d . . . . .
H9 H 1.161737 0.354070 0.311916 0.025 Uiso 1 1 calc R U . . .
C10 C 1.1051(4) 0.47753(11) 0.31450(7) 0.0210(4) Uani 1 1 d . . . . .
C11 C 1.3248(4) 0.50512(12) 0.34962(7) 0.0218(4) Uani 1 1 d . . . . .
H11A H 1.418692 0.554430 0.333594 0.026 Uiso 1 1 calc R U . . .
H11B H 1.453717 0.457630 0.353668 0.026 Uiso 1 1 calc R U . . .
C12 C 1.2168(4) 0.53104(15) 0.40415(8) 0.0316(5) Uani 1 1 d . . . . .
H12A H 1.087713 0.578408 0.399742 0.038 Uiso 1 1 calc R U . . .
H12B H 1.120981 0.481670 0.419668 0.038 Uiso 1 1 calc R U . . .
C13 C 1.4322(4) 0.55928(13) 0.44172(7) 0.0250(4) Uani 1 1 d . . . . .
C14 C 0.5783(4) 0.24309(12) 0.23347(7) 0.0225(4) Uani 1 1 d . . . . .
C15 C 1.5035(4) 0.64520(13) 0.44574(7) 0.0267(4) Uani 1 1 d . . . . .
H15 H 1.416828 0.686630 0.424352 0.032 Uiso 1 1 calc R U . . .
C16 C 1.6999(4) 0.67107(13) 0.48068(8) 0.0265(4) Uani 1 1 d . . . . .
H16 H 1.748124 0.729899 0.482549 0.032 Uiso 1 1 calc R U . . .
C17 C 1.8254(4) 0.61242(14) 0.51263(7) 0.0272(4) Uani 1 1 d . . . . .
H17 H 1.956348 0.630700 0.537124 0.033 Uiso 1 1 calc R U . . .
C18 C 1.7586(5) 0.52619(14) 0.50869(7) 0.0297(5) Uani 1 1 d . . . . .
H18 H 1.844830 0.485007 0.530332 0.036 Uiso 1 1 calc R U . . .
C19 C 1.5656(5) 0.50047(13) 0.47303(8) 0.0286(4) Uani 1 1 d . . . . .
H19 H 1.523841 0.441256 0.470000 0.034 Uiso 1 1 calc R U . . .
C20 C 1.0241(4) 0.16888(12) 0.30771(8) 0.0247(4) Uani 1 1 d . . . . .
H20 H 1.134477 0.154895 0.278591 0.030 Uiso 1 1 calc R U . . .
C21 C 1.0165(4) 0.12597(12) 0.35420(8) 0.0264(4) Uani 1 1 d . . . . .
H21 H 1.124154 0.078417 0.363780 0.032 Uiso 1 1 calc R U . . .
C22 C 0.8162(4) 0.16553(12) 0.38622(7) 0.0235(4) Uani 1 1 d . . . . .
C23 C 0.7073(4) 0.23370(11) 0.35661(7) 0.0204(4) Uani 1 1 d . . . . .
C24 C 0.4118(4) 0.27063(13) 0.41805(7) 0.0263(4) Uani 1 1 d . . . . .
H24 H 0.269924 0.305864 0.429952 0.032 Uiso 1 1 calc R U . . .
C25 C 0.5009(5) 0.20595(13) 0.45152(7) 0.0284(4) Uani 1 1 d . . . . .
H25 H 0.421367 0.198643 0.485156 0.034 Uiso 1 1 calc R U . . .
C26 C 0.7055(4) 0.15226(13) 0.43584(8) 0.0282(4) Uani 1 1 d . . . . .
H26 H 0.768220 0.107807 0.458212 0.034 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 C10 1.357(2) . ?
O1 C14 1.221(2) . ?
N1 N2 1.388(2) . ?
N1 C8 1.414(2) . ?
N1 C14 1.402(2) . ?
N2 C20 1.385(3) . ?
N2 C23 1.383(2) . ?
N3 C23 1.323(2) . ?
N3 C24 1.343(2) . ?
C1 C2 1.404(3) . ?
C1 C6 1.403(3) . ?
C1 C14 1.463(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(3) . ?
C6 C7 1.435(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.350(3) . ?
C8 C9 1.463(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.327(3) . ?
C10 C11 1.484(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.541(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.510(3) . ?
C13 C15 1.390(3) . ?
C13 C19 1.387(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.376(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.357(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.434(3) . ?
C22 C23 1.413(3) . ?
C22 C26 1.393(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.385(3) . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C8 118.62(15) . . ?
N2 N1 C14 115.15(15) . . ?
C14 N1 C8 125.58(16) . . ?
C20 N2 N1 125.52(15) . . ?
C23 N2 N1 122.75(15) . . ?
C23 N2 C20 109.47(15) . . ?
C23 N3 C24 113.57(16) . . ?
C2 C1 C14 118.72(18) . . ?
C6 C1 C2 120.56(18) . . ?
C6 C1 C14 120.66(17) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.21(19) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.64(19) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.22(19) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.56(18) . . ?
C1 C6 C7 119.67(17) . . ?
C5 C6 C7 121.77(18) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.66(17) . . ?
C8 C7 H7 119.2 . . ?
N1 C8 C9 115.79(16) . . ?
C7 C8 N1 117.77(17) . . ?
C7 C8 C9 126.34(17) . . ?
C8 C9 H9 116.5 . . ?
C10 C9 C8 126.93(18) . . ?
C10 C9 H9 116.5 . . ?
F1 C10 C11 112.26(15) . . ?
C9 C10 F1 120.38(17) . . ?
C9 C10 C11 127.29(17) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 C12 110.68(16) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 113.00(17) . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C15 C13 C12 120.84(19) . . ?
C19 C13 C12 121.1(2) . . ?
C19 C13 C15 118.03(19) . . ?
O1 C14 N1 120.20(18) . . ?
O1 C14 C1 125.23(18) . . ?
N1 C14 C1 114.55(16) . . ?
C13 C15 H15 119.6 . . ?
C16 C15 C13 120.71(19) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.70(19) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.31(19) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.74(19) . . ?
C19 C18 H18 120.1 . . ?
C13 C19 C18 121.47(19) . . ?
C13 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
N2 C20 H20 125.5 . . ?
C21 C20 N2 109.06(17) . . ?
C21 C20 H20 125.5 . . ?
C20 C21 H21 126.2 . . ?
C20 C21 C22 107.51(17) . . ?
C22 C21 H21 126.2 . . ?
C23 C22 C21 107.14(16) . . ?
C26 C22 C21 136.88(19) . . ?
C26 C22 C23 115.96(18) . . ?
N2 C23 C22 106.67(16) . . ?
N3 C23 N2 125.19(16) . . ?
N3 C23 C22 128.14(17) . . ?
N3 C24 H24 117.8 . . ?
N3 C24 C25 124.35(19) . . ?
C25 C24 H24 117.8 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.11(18) . . ?
C26 C25 H25 119.9 . . ?
C22 C26 H26 121.1 . . ?
C25 C26 C22 117.87(18) . . ?
C25 C26 H26 121.1 . . ?

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 C10 C11 C12 69.6(2) . . . . ?
N1 N2 C20 C21 -167.15(17) . . . . ?
N1 N2 C23 N3 -13.0(3) . . . . ?
N1 N2 C23 C22 167.47(16) . . . . ?
N1 C8 C9 C10 -160.09(18) . . . . ?
N2 N1 C8 C7 -167.43(16) . . . . ?
N2 N1 C8 C9 15.9(2) . . . . ?
N2 N1 C14 O1 -10.9(3) . . . . ?
N2 N1 C14 C1 167.46(15) . . . . ?
N2 C20 C21 C22 2.5(2) . . . . ?
N3 C24 C25 C26 -0.6(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C6 C7 C8 -2.4(3) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 C7 179.39(17) . . . . ?
C2 C1 C14 O1 1.4(3) . . . . ?
C2 C1 C14 N1 -176.81(16) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -179.89(18) . . . . ?
C5 C6 C7 C8 178.14(18) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C6 C1 C14 O1 178.86(18) . . . . ?
C6 C1 C14 N1 0.6(3) . . . . ?
C6 C7 C8 N1 0.1(3) . . . . ?
C6 C7 C8 C9 176.28(17) . . . . ?
C7 C8 C9 C10 23.6(3) . . . . ?
C8 N1 N2 C20 -113.4(2) . . . . ?
C8 N1 N2 C23 85.5(2) . . . . ?
C8 N1 C14 O1 178.48(17) . . . . ?
C8 N1 C14 C1 -3.2(3) . . . . ?
C8 C9 C10 F1 3.7(3) . . . . ?
C8 C9 C10 C11 -179.40(18) . . . . ?
C9 C10 C11 C12 -107.5(2) . . . . ?
C10 C11 C12 C13 179.67(17) . . . . ?
C11 C12 C13 C15 92.0(2) . . . . ?
C11 C12 C13 C19 -87.7(2) . . . . ?
C12 C13 C15 C16 179.38(18) . . . . ?
C12 C13 C19 C18 -178.19(18) . . . . ?
C13 C15 C16 C17 -1.0(3) . . . . ?
C14 N1 N2 C20 75.2(2) . . . . ?
C14 N1 N2 C23 -85.9(2) . . . . ?
C14 N1 C8 C7 2.9(3) . . . . ?
C14 N1 C8 C9 -173.71(17) . . . . ?
C14 C1 C2 C3 178.32(18) . . . . ?
C14 C1 C6 C5 -178.52(17) . . . . ?
C14 C1 C6 C7 2.0(3) . . . . ?
C15 C13 C19 C18 2.1(3) . . . . ?
C15 C16 C17 C18 1.7(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C13 -1.4(3) . . . . ?
C19 C13 C15 C16 -0.9(3) . . . . ?
C20 N2 C23 N3 -176.80(17) . . . . ?
C20 N2 C23 C22 3.7(2) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C20 C21 C22 C26 177.8(2) . . . . ?
C21 C22 C23 N2 -2.1(2) . . . . ?
C21 C22 C23 N3 178.39(18) . . . . ?
C21 C22 C26 C25 -177.6(2) . . . . ?
C23 N2 C20 C21 -3.9(2) . . . . ?
C23 N3 C24 C25 0.8(3) . . . . ?
C23 C22 C26 C25 0.2(3) . . . . ?
C24 N3 C23 N2 -179.80(18) . . . . ?
C24 N3 C23 C22 -0.4(3) . . . . ?
C24 C25 C26 C22 0.1(3) . . . . ?
C26 C22 C23 N2 179.41(17) . . . . ?
C26 C22 C23 N3 -0.1(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 1.632
_oxdiff_exptl_absorpt_empirical_full_min 0.477
####################################################################### 
# 
# 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_ly432
_database_code_depnum_ccdc_archive 'CCDC 2502550'
loop_
_audit_author_name
_audit_author_address
Yang
;Guangzhou Medical University
China
;
_audit_update_record             
;
2025-11-13 deposited with the CCDC.	2026-05-11 downloaded from the CCDC.
;
_audit_creation_date             2025-01-20
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H27 F N2 O2'
_chemical_formula_sum            'C30 H27 F N2 O2'
_chemical_formula_weight         466.53
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N F S Cl'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.0172(4)
_cell_length_b                   9.2833(4)
_cell_length_c                   12.6711(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.968(4)
_cell_angle_gamma                90
_cell_volume                     1176.74(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5005
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      72.4860
_cell_measurement_theta_min      3.4200
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8594
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.879
_diffrn_reflns_theta_min         3.493
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -19.00   0.50    0.05    --   36.77 -19.00-150.00   62
  2  ω    -48.00 -18.00   0.50    0.05    --   36.77 -19.00-180.00   60
  3  ω    -33.00  21.00   0.50    0.05    --   36.77 -40.00 -51.00  108
  4  ω     33.00  72.00   0.50    0.08    --  109.42 -77.00  60.00   78
  5  ω     33.00  65.00   0.50    0.08    --  109.42 -77.00-150.00   64
  6  ω     89.00 118.00   0.50    0.08    --  109.42  30.00-150.00   58
  7  ω    127.00 169.00   0.50    0.08    --  109.42  30.00-150.00   84
  8  ω     88.00 122.00   0.50    0.08    --  109.42  40.00 102.00   68
  9  ω     88.00 140.00   0.50    0.08    --  109.42  61.00 150.00  104
 10  ω     38.00 119.00   0.50    0.05    --   36.77  40.00 102.00  162
 11  ω    -48.00 -22.00   0.50    0.05    --  -36.77 -40.00 -51.00   52
 12  ω    -52.00 -20.00   0.50    0.05    --  -36.77 -57.00 120.00   64
 13  ω    -54.00 -12.00   0.50    0.05    --  -36.77 -57.00 150.00   84
 14  ω    -56.00 -10.00   0.50    0.05    --  -36.77 -57.00  90.00   92
 15  ω    -54.00 -29.00   0.50    0.05    --  -36.77 -57.00-180.00   50
 16  ω   -125.00 -37.00   0.50    0.08    -- -103.00 -15.00-180.00  176
 17  ω   -159.00-119.00   0.50    0.08    -- -103.00 -40.00 -51.00   80
 18  ω   -161.00 -77.00   0.50    0.08    -- -103.00 -30.00 -30.00  168
 19  ω   -174.00-130.00   0.50    0.08    -- -103.00 -45.00  30.00   88
 20  ω   -111.00 -74.00   0.50    0.08    -- -103.00 -45.00  30.00   74
 21  ω    -10.00  15.00   0.50    0.05    --  -36.77  40.00 102.00   50
 22  ω    -72.00 -27.00   0.50    0.08    -- -103.00  77.00  30.00   90
 23  ω    -53.00 -27.00   0.50    0.08    -- -103.00  77.00-150.00   52
 24  ω     56.00  87.00   0.50    0.08    --  109.42-112.00-120.00   62
 25  ω   -106.00 -29.00   0.50    0.08    -- -103.00 140.00-150.00  154
 26  ω    -88.00 -63.00   0.50    0.08    -- -103.00 112.00 120.00   50
 27  ω    -58.00 -33.00   0.50    0.08    -- -103.00 112.00 120.00   50
 28  ω   -116.00 -90.00   0.50    0.50    -- -103.00 -40.00 -51.00   52
 29  ω    -89.00 -64.00   0.50    0.20    --  -36.77 -40.00 -51.00   50
 30  ω    -89.00 -64.00   0.50    0.20    --  -36.77 -40.00 -51.00   50
 31  ω   -160.00-134.00   0.50    0.50    -- -103.00 -40.00 -51.00   52
 32  ω    -56.00 -11.00   0.50    0.20    --  -36.77 -57.00-150.00   90
 33  ω      9.00  35.00   0.50    0.20    --   36.77  70.00 -94.22   52
 34  ω      6.00  31.00   0.50    0.20    --   36.77  72.00  68.90   50
 35  ω     48.00  76.00   0.50    0.20    --   36.77 -99.00 150.00   56
 36  ω     27.00  68.00   0.50    0.20    --   36.77-140.00 -30.00   82
 37  ω     18.00  43.00   0.50    0.20    --   36.77 -99.00 150.00   50
 38  ω     75.00 101.00   0.50    0.20    --   36.77-140.00 -30.00   52
 39  ω    -51.00 -26.00   0.50    0.20    --   36.77 -19.00  30.00   50
 40  ω   -100.00 -75.00   0.50    0.50    -- -103.00 -51.00-176.74   50
 41  ω   -118.00 -75.00   0.50    0.50    -- -103.00 -45.00-180.00   86
 42  ω   -102.00 -76.00   0.50    0.50    -- -103.00 -46.00 160.78   52
 43  ω    -72.00 -47.00   0.50    0.50    -- -103.00  77.00 120.00   50
 44  ω    -99.00 -74.00   0.50    0.50    -- -103.00 -53.00-155.79   50
 45  ω   -102.00 -76.00   0.50    0.50    -- -103.00 -47.00 157.62   52
 46  ω   -102.00 -91.50   0.50    0.50    -- -103.00 -53.00 172.55   21
;
_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      0.0718552000
_diffrn_orient_matrix_UB_12      -0.0750631000
_diffrn_orient_matrix_UB_13      0.0953462000
_diffrn_orient_matrix_UB_21      0.1184414000
_diffrn_orient_matrix_UB_22      -0.0360285000
_diffrn_orient_matrix_UB_23      -0.0682200000
_diffrn_orient_matrix_UB_31      0.0672940000
_diffrn_orient_matrix_UB_32      0.1435519000
_diffrn_orient_matrix_UB_33      0.0327752000
_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         0.665
_reflns_Friedel_fraction_full    0.787
_reflns_Friedel_fraction_max     0.723
_reflns_number_gt                3457
_reflns_number_total             3984
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.008
_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)+(0.1277P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1660
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C29(H29A,H29B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C35(H35A,H35B,H35C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1773(2) 0.4231(3) 0.47912(19) 0.0486(7) Uani 1 1 d . . . . .
O1 O 0.2601(3) 0.4626(3) 0.97383(19) 0.0327(6) Uani 1 1 d . . . . .
O2 O 0.7041(3) 0.3962(3) 0.9007(3) 0.0496(8) Uani 1 1 d . . . . .
N1 N 0.2888(3) 0.4362(3) 0.7983(2) 0.0283(6) Uani 1 1 d . . . . .
N2 N 0.5460(4) 0.5510(4) 0.8367(3) 0.0444(9) Uani 1 1 d . . . . .
C1 C 0.1486(3) 0.6290(4) 0.8569(3) 0.0275(7) Uani 1 1 d . . . . .
C2 C 0.0883(4) 0.7035(4) 0.9373(3) 0.0326(8) Uani 1 1 d . . . . .
H2 H 0.110974 0.679994 1.008930 0.039 Uiso 1 1 calc R U . . .
C3 C -0.0038(4) 0.8106(4) 0.9141(3) 0.0341(8) Uani 1 1 d . . . . .
H3 H -0.043925 0.860322 0.969825 0.041 Uiso 1 1 calc R U . . .
C4 C -0.0386(4) 0.8468(4) 0.8087(3) 0.0312(8) Uani 1 1 d . . . . .
C5 C 0.0235(4) 0.7770(4) 0.7288(3) 0.0305(8) Uani 1 1 d . . . . .
H5 H 0.002203 0.803323 0.657478 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1185(4) 0.6668(4) 0.7509(3) 0.0283(8) Uani 1 1 d . . . . .
C7 C 0.1843(4) 0.5925(4) 0.6696(3) 0.0298(8) Uani 1 1 d . . . . .
H7 H 0.170483 0.622659 0.598220 0.036 Uiso 1 1 calc R U . . .
C8 C 0.2662(3) 0.4797(4) 0.6931(3) 0.0277(7) Uani 1 1 d . . . . .
C9 C 0.3394(4) 0.3991(4) 0.6144(3) 0.0309(8) Uani 1 1 d . . . . .
H9 H 0.423638 0.360415 0.637665 0.037 Uiso 1 1 calc R U . . .
C10 C 0.3003(4) 0.3752(4) 0.5154(3) 0.0325(8) Uani 1 1 d . . . . .
C11 C 0.3685(4) 0.3009(5) 0.4292(3) 0.0405(9) Uani 1 1 d . . . . .
H11A H 0.395035 0.374617 0.377885 0.049 Uiso 1 1 calc R U . . .
H11B H 0.302816 0.236625 0.391891 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4918(4) 0.2117(5) 0.4615(3) 0.0432(10) Uani 1 1 d . . . . .
H12A H 0.466904 0.143064 0.516934 0.052 Uiso 1 1 calc R U . . .
H12B H 0.516112 0.154143 0.399561 0.052 Uiso 1 1 calc R U . . .
C13 C 0.6146(4) 0.2924(4) 0.5021(3) 0.0388(9) Uani 1 1 d . . . . .
C14 C 0.6740(5) 0.3944(5) 0.4391(4) 0.0481(11) Uani 1 1 d . . . . .
H14 H 0.635336 0.416100 0.370876 0.058 Uiso 1 1 calc R U . . .
C15 C 0.7907(5) 0.4652(6) 0.4761(5) 0.0647(15) Uani 1 1 d . . . . .
H15 H 0.830719 0.535042 0.432967 0.078 Uiso 1 1 calc R U . . .
C16 C 0.8481(5) 0.4339(6) 0.5754(6) 0.0684(16) Uani 1 1 d . . . . .
H16 H 0.926265 0.483075 0.601315 0.082 Uiso 1 1 calc R U . . .
C17 C 0.7894(5) 0.3298(6) 0.6361(5) 0.0608(14) Uani 1 1 d . . . . .
H17 H 0.829063 0.305187 0.703470 0.073 Uiso 1 1 calc R U . . .
C18 C 0.6743(5) 0.2620(5) 0.5996(4) 0.0479(10) Uani 1 1 d . . . . .
H18 H 0.634870 0.191997 0.642952 0.057 Uiso 1 1 calc R U . . .
C19 C 0.2374(3) 0.5064(4) 0.8836(3) 0.0272(7) Uani 1 1 d . . . . .
C20 C 0.1290(4) 0.1888(5) 0.7813(4) 0.0454(10) Uani 1 1 d . . . . .
H20A H 0.082395 0.239615 0.836311 0.068 Uiso 1 1 calc R U . . .
H20B H 0.091378 0.091981 0.771857 0.068 Uiso 1 1 calc R U . . .
H20C H 0.118030 0.242191 0.714660 0.068 Uiso 1 1 calc R U . . .
C21 C 0.2761(4) 0.1776(4) 0.8137(3) 0.0356(8) Uani 1 1 d . . . . .
C22 C 0.3336(4) 0.0454(5) 0.8392(3) 0.0424(10) Uani 1 1 d . . . . .
H22 H 0.281125 -0.039828 0.833665 0.051 Uiso 1 1 calc R U . . .
C23 C 0.4685(4) 0.0371(5) 0.8731(3) 0.0422(9) Uani 1 1 d . . . . .
H23 H 0.507544 -0.053491 0.891108 0.051 Uiso 1 1 calc R U . . .
C24 C 0.5439(4) 0.1597(5) 0.8802(3) 0.0403(9) Uani 1 1 d . . . . .
H24 H 0.635378 0.152813 0.903536 0.048 Uiso 1 1 calc R U . . .
C25 C 0.4910(4) 0.2942(4) 0.8543(3) 0.0331(8) Uani 1 1 d . . . . .
C26 C 0.3543(4) 0.3006(4) 0.8222(3) 0.0309(8) Uani 1 1 d . . . . .
C27 C 0.5768(4) 0.4227(5) 0.8622(3) 0.0361(8) Uani 1 1 d . . . . .
C29 C 0.6665(5) 0.6398(5) 0.8623(4) 0.0498(11) Uani 1 1 d . . . . .
H29A H 0.649768 0.709470 0.919259 0.060 Uiso 1 1 calc R U . . .
H29B H 0.693364 0.693439 0.799227 0.060 Uiso 1 1 calc R U . . .
C30 C 0.7732(5) 0.5321(6) 0.8980(4) 0.0485(11) Uani 1 1 d . . . . .
H30A H 0.845388 0.528748 0.847631 0.058 Uiso 1 1 calc R U . . .
H30B H 0.812403 0.557426 0.968917 0.058 Uiso 1 1 calc R U . . .
C35 C -0.1439(4) 0.9606(4) 0.7844(3) 0.0369(9) Uani 1 1 d . . . . .
H35A H -0.232333 0.921570 0.797862 0.055 Uiso 1 1 calc R U . . .
H35B H -0.141669 0.989070 0.710020 0.055 Uiso 1 1 calc R U . . .
H35C H -0.125976 1.044827 0.829527 0.055 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 C10 1.367(4) . ?
O1 C19 1.224(4) . ?
O2 C27 1.363(5) . ?
O2 C30 1.441(6) . ?
N1 C8 1.401(4) . ?
N1 C19 1.384(5) . ?
N1 C26 1.444(5) . ?
N2 C27 1.268(6) . ?
N2 C29 1.484(5) . ?
C1 C2 1.394(5) . ?
C1 C6 1.405(5) . ?
C1 C19 1.473(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(5) . ?
C4 C5 1.377(5) . ?
C4 C35 1.514(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.415(5) . ?
C6 C7 1.429(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.353(5) . ?
C8 C9 1.472(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.314(5) . ?
C10 C11 1.488(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.525(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.507(6) . ?
C13 C14 1.392(6) . ?
C13 C18 1.374(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.400(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(9) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.373(7) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C21 1.513(6) . ?
C21 C22 1.387(6) . ?
C21 C26 1.385(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.399(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.367(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(5) . ?
C25 C26 1.409(5) . ?
C25 C27 1.470(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.516(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C27 O2 C30 106.0(3) . . ?
C8 N1 C26 120.0(3) . . ?
C19 N1 C8 124.0(3) . . ?
C19 N1 C26 115.5(3) . . ?
C27 N2 C29 106.4(3) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 C19 119.6(3) . . ?
C6 C1 C19 120.6(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C35 119.8(3) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 C35 121.0(3) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 119.0(3) . . ?
C5 C6 C7 122.5(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
N1 C8 C9 115.9(3) . . ?
C7 C8 N1 119.9(3) . . ?
C7 C8 C9 124.2(3) . . ?
C8 C9 H9 116.6 . . ?
C10 C9 C8 126.7(3) . . ?
C10 C9 H9 116.6 . . ?
F1 C10 C11 110.1(3) . . ?
C9 C10 F1 119.0(3) . . ?
C9 C10 C11 130.8(4) . . ?
C10 C11 H11A 108.1 . . ?
C10 C11 H11B 108.1 . . ?
C10 C11 C12 116.8(3) . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C11 C12 H12A 108.0 . . ?
C11 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
C13 C12 C11 117.2(4) . . ?
C13 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C14 C13 C12 120.5(4) . . ?
C18 C13 C12 121.0(4) . . ?
C18 C13 C14 118.4(4) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(5) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(5) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.8(5) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(5) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.1 . . ?
C17 C18 C13 121.9(5) . . ?
C17 C18 H18 119.1 . . ?
O1 C19 N1 120.9(3) . . ?
O1 C19 C1 123.5(3) . . ?
N1 C19 C1 115.4(3) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
C22 C21 C20 120.7(4) . . ?
C26 C21 C20 120.2(4) . . ?
C26 C21 C22 119.1(4) . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(4) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(4) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.0 . . ?
C23 C24 C25 122.0(4) . . ?
C25 C24 H24 119.0 . . ?
C24 C25 C26 117.3(4) . . ?
C24 C25 C27 119.9(3) . . ?
C26 C25 C27 122.8(3) . . ?
C21 C26 N1 117.0(3) . . ?
C21 C26 C25 121.6(4) . . ?
C25 C26 N1 121.4(3) . . ?
O2 C27 C25 114.3(3) . . ?
N2 C27 O2 118.1(4) . . ?
N2 C27 C25 127.6(3) . . ?
N2 C29 H29A 110.8 . . ?
N2 C29 H29B 110.8 . . ?
N2 C29 C30 104.6(4) . . ?
H29A C29 H29B 108.9 . . ?
C30 C29 H29A 110.8 . . ?
C30 C29 H29B 110.8 . . ?
O2 C30 C29 104.6(3) . . ?
O2 C30 H30A 110.8 . . ?
O2 C30 H30B 110.8 . . ?
C29 C30 H30A 110.8 . . ?
C29 C30 H30B 110.8 . . ?
H30A C30 H30B 108.9 . . ?
C4 C35 H35A 109.5 . . ?
C4 C35 H35B 109.5 . . ?
C4 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C10 C11 C12 -166.6(3) . . . . ?
N1 C8 C9 C10 150.1(4) . . . . ?
N2 C29 C30 O2 -5.6(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C6 C7 C8 5.3(5) . . . . ?
C2 C1 C6 C5 -2.2(5) . . . . ?
C2 C1 C6 C7 178.0(3) . . . . ?
C2 C1 C19 O1 1.6(5) . . . . ?
C2 C1 C19 N1 177.9(3) . . . . ?
C2 C3 C4 C5 -2.0(5) . . . . ?
C2 C3 C4 C35 177.6(3) . . . . ?
C3 C4 C5 C6 1.9(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
C5 C6 C7 C8 -174.5(3) . . . . ?
C6 C1 C2 C3 2.1(5) . . . . ?
C6 C1 C19 O1 -175.0(3) . . . . ?
C6 C1 C19 N1 1.2(5) . . . . ?
C6 C7 C8 N1 -1.1(5) . . . . ?
C6 C7 C8 C9 -178.9(3) . . . . ?
C7 C8 C9 C10 -32.0(6) . . . . ?
C8 N1 C19 O1 179.6(3) . . . . ?
C8 N1 C19 C1 3.2(5) . . . . ?
C8 N1 C26 C21 -80.6(4) . . . . ?
C8 N1 C26 C25 100.4(4) . . . . ?
C8 C9 C10 F1 -2.8(6) . . . . ?
C8 C9 C10 C11 177.2(4) . . . . ?
C9 C10 C11 C12 13.4(7) . . . . ?
C10 C11 C12 C13 -68.6(5) . . . . ?
C11 C12 C13 C14 -59.3(5) . . . . ?
C11 C12 C13 C18 124.0(4) . . . . ?
C12 C13 C14 C15 -177.8(4) . . . . ?
C12 C13 C18 C17 177.2(4) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
C14 C13 C18 C17 0.4(6) . . . . ?
C14 C15 C16 C17 1.2(8) . . . . ?
C15 C16 C17 C18 -1.8(8) . . . . ?
C16 C17 C18 C13 1.0(7) . . . . ?
C18 C13 C14 C15 -1.0(6) . . . . ?
C19 N1 C8 C7 -3.4(5) . . . . ?
C19 N1 C8 C9 174.6(3) . . . . ?
C19 N1 C26 C21 91.5(4) . . . . ?
C19 N1 C26 C25 -87.4(4) . . . . ?
C19 C1 C2 C3 -174.6(3) . . . . ?
C19 C1 C6 C5 174.5(3) . . . . ?
C19 C1 C6 C7 -5.3(5) . . . . ?
C20 C21 C22 C23 -177.5(4) . . . . ?
C20 C21 C26 N1 -0.3(5) . . . . ?
C20 C21 C26 C25 178.7(4) . . . . ?
C21 C22 C23 C24 -0.5(7) . . . . ?
C22 C21 C26 N1 -177.9(4) . . . . ?
C22 C21 C26 C25 1.1(6) . . . . ?
C22 C23 C24 C25 -0.2(7) . . . . ?
C23 C24 C25 C26 1.3(6) . . . . ?
C23 C24 C25 C27 -179.4(4) . . . . ?
C24 C25 C26 N1 177.1(3) . . . . ?
C24 C25 C26 C21 -1.8(5) . . . . ?
C24 C25 C27 O2 -3.0(5) . . . . ?
C24 C25 C27 N2 176.1(4) . . . . ?
C26 N1 C8 C7 168.0(3) . . . . ?
C26 N1 C8 C9 -13.9(4) . . . . ?
C26 N1 C19 O1 7.8(5) . . . . ?
C26 N1 C19 C1 -168.5(3) . . . . ?
C26 C21 C22 C23 0.1(6) . . . . ?
C26 C25 C27 O2 176.3(3) . . . . ?
C26 C25 C27 N2 -4.6(6) . . . . ?
C27 O2 C30 C29 4.6(5) . . . . ?
C27 N2 C29 C30 4.8(5) . . . . ?
C27 C25 C26 N1 -2.2(5) . . . . ?
C27 C25 C26 C21 179.0(3) . . . . ?
C29 N2 C27 O2 -2.1(5) . . . . ?
C29 N2 C27 C25 178.8(4) . . . . ?
C30 O2 C27 N2 -1.7(5) . . . . ?
C30 O2 C27 C25 177.5(3) . . . . ?
C35 C4 C5 C6 -177.6(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 4.697
_oxdiff_exptl_absorpt_empirical_full_min 0.556
