# Supplementary Information (SI) for ChemComm.
# 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 
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data_ov_z-3an2pa-cf3_auto
_database_code_depnum_ccdc_archive 'CCDC 2429964'
loop_
_audit_author_name
_audit_author_address
'Zhengcheng Wang'
;Qingdao University
China
;
_audit_update_record             
;
2025-07-02 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H14 F3 N'
_chemical_formula_sum            'C24 H14 F3 N'
_chemical_formula_weight         373.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   4.67530(10)
_cell_length_b                   36.9040(11)
_cell_length_c                   10.6315(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.522(3)
_cell_angle_gamma                90
_cell_volume                     1803.49(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    303.3(4)
_cell_measurement_reflns_used    3883
_cell_measurement_theta_min      2.3790
_cell_measurement_theta_max      74.0850
_shelx_estimated_absorpt_T_max   0.862
_shelx_estimated_absorpt_T_min   0.773
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11705
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.371
_diffrn_reflns_theta_min         2.395
_diffrn_ambient_temperature      303.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2537
_reflns_number_total             3584
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      1.104
_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)+(0.0770P)²+0.4967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1772
_refine_ls_wR_factor_ref         0.1895
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F2-C24 \\sim F0-C24
 with sigma of 0.02
 F1-C24 \\sim F4-C24
 with sigma of 0.02
 F3-C24 \\sim F5-C24
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F2 \\sim F3 \\sim F1 \\sim C24 \\sim F0 \\sim F4 \\sim F5: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(F0)=Sof(F4)=Sof(F5)=1-FVAR(1)
 Sof(F2)=Sof(F3)=Sof(F1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C10(H10), C1(H1), C23(H23), C22(H22), C11(H11), C13(H13),
 C19(H19), C12(H12), C4(H4), C2(H2), C20(H20), C3(H3)
;
_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
F2 F 0.0781(7) 0.48783(8) 0.7117(2) 0.1253(11) Uani 0.885(5) 1 d D U P A 1
F3 F 0.2226(10) 0.51653(8) 0.8821(3) 0.1347(11) Uani 0.885(5) 1 d D U P A 1
F1 F 0.5080(7) 0.48100(9) 0.8091(4) 0.1387(13) Uani 0.885(5) 1 d D U P A 1
C7 C 0.7402(5) 0.65266(7) 0.2782(2) 0.0677(6) Uani 1 1 d . . . . .
C8 C 0.6741(5) 0.68969(7) 0.2925(2) 0.0702(6) Uani 1 1 d . . . . .
C18 C 0.6022(5) 0.59182(6) 0.5605(2) 0.0669(6) Uani 1 1 d . . . . .
C16 C 0.7118(5) 0.62088(6) 0.4863(2) 0.0681(6) Uani 1 1 d . . . . .
C6 C 0.8845(5) 0.64154(7) 0.1803(2) 0.0716(6) Uani 1 1 d . . . . .
N1 N 1.0866(6) 0.66377(8) 0.6174(3) 0.1058(9) Uani 1 1 d . . . . .
C9 C 0.7683(6) 0.71573(7) 0.2092(2) 0.0768(7) Uani 1 1 d . . . . .
C17 C 0.9192(6) 0.64553(7) 0.5579(2) 0.0766(7) Uani 1 1 d . . . . .
C21 C 0.4050(6) 0.53600(7) 0.7010(2) 0.0752(7) Uani 1 1 d . . . . .
C5 C 0.9753(6) 0.66810(9) 0.0975(2) 0.0801(7) Uani 1 1 d . . . . .
C15 C 0.6417(6) 0.62474(7) 0.3590(2) 0.0754(7) Uani 1 1 d . . . . .
H15 H 0.514332 0.607527 0.316365 0.090 Uiso 1 1 calc R U . . .
C14 C 0.5067(6) 0.70264(8) 0.3823(3) 0.0817(7) Uani 1 1 d . . . . .
H14 H 0.438881 0.686338 0.436767 0.098 Uiso 1 1 calc R U . . .
C10 C 0.9171(6) 0.70428(8) 0.1161(3) 0.0846(8) Uani 1 1 d . . . . .
H10 H 0.980987 0.721509 0.063646 0.101 Uiso 1 1 calc R U . . .
C1 C 0.9482(6) 0.60452(8) 0.1590(3) 0.0888(8) Uani 1 1 d . . . . .
H1 H 0.890341 0.586647 0.210750 0.107 Uiso 1 1 calc R U . . .
C23 C 0.6805(7) 0.58991(8) 0.6920(3) 0.0874(8) Uani 1 1 d . . . . .
H23 H 0.801345 0.607701 0.735008 0.105 Uiso 1 1 calc R U . . .
C24 C 0.3076(8) 0.50576(9) 0.7753(3) 0.0923(8) Uani 1 1 d D U . . .
C22 C 0.5847(7) 0.56246(8) 0.7609(3) 0.0910(8) Uani 1 1 d . . . . .
H22 H 0.642685 0.561846 0.849285 0.109 Uiso 1 1 calc R U . . .
C11 C 0.7020(8) 0.75311(8) 0.2242(3) 0.0969(9) Uani 1 1 d . . . . .
H11 H 0.768953 0.770258 0.172402 0.116 Uiso 1 1 calc R U . . .
C13 C 0.4447(7) 0.73834(10) 0.3897(3) 0.0989(10) Uani 1 1 d . . . . .
H13 H 0.332489 0.746109 0.448254 0.119 Uiso 1 1 calc R U . . .
C19 C 0.4175(7) 0.56521(9) 0.5019(3) 0.1002(10) Uani 1 1 d . . . . .
H19 H 0.356928 0.565784 0.413581 0.120 Uiso 1 1 calc R U . . .
C12 C 0.5475(9) 0.76393(9) 0.3100(4) 0.1088(11) Uani 1 1 d . . . . .
H12 H 0.506742 0.788409 0.317681 0.131 Uiso 1 1 calc R U . . .
C4 C 1.1235(7) 0.65637(13) -0.0006(3) 0.1042(10) Uani 1 1 d . . . . .
H4 H 1.183058 0.673513 -0.054565 0.125 Uiso 1 1 calc R U . . .
C2 C 1.0932(8) 0.59498(11) 0.0635(4) 0.1102(12) Uani 1 1 d . . . . .
H2 H 1.135441 0.570720 0.051787 0.132 Uiso 1 1 calc R U . . .
C20 C 0.3214(8) 0.53793(9) 0.5711(3) 0.1053(11) Uani 1 1 d . . . . .
H20 H 0.196880 0.520381 0.528886 0.126 Uiso 1 1 calc R U . . .
C3 C 1.1796(8) 0.62147(15) -0.0174(4) 0.1186(13) Uani 1 1 d . . . . .
H3 H 1.276109 0.614579 -0.082746 0.142 Uiso 1 1 calc R U . . .
F0 F 0.313(7) 0.4760(4) 0.7097(19) 0.122(5) Uani 0.115(5) 1 d D U P A 2
F4 F 0.505(5) 0.5022(7) 0.8811(19) 0.124(5) Uani 0.115(5) 1 d D U P A 2
F5 F 0.074(4) 0.5125(7) 0.808(3) 0.130(5) Uani 0.115(5) 1 d D U P A 2


_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
F2 C24 1.335(4) . ?
F3 C24 1.330(4) . ?
F1 C24 1.311(4) . ?
C7 C8 1.415(3) . ?
C7 C6 1.401(4) . ?
C7 C15 1.468(4) . ?
C8 C9 1.430(4) . ?
C8 C14 1.423(4) . ?
C18 C16 1.477(4) . ?
C18 C23 1.381(3) . ?
C18 C19 1.379(4) . ?
C16 C17 1.441(3) . ?
C16 C15 1.341(3) . ?
C6 C5 1.433(4) . ?
C6 C1 1.425(4) . ?
N1 C17 1.133(3) . ?
C9 C10 1.377(4) . ?
C9 C11 1.429(4) . ?
C21 C24 1.486(4) . ?
C21 C22 1.367(4) . ?
C21 C20 1.367(4) . ?
C5 C10 1.384(4) . ?
C5 C4 1.421(4) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.354(4) . ?
C10 H10 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.366(5) . ?
C23 H23 0.9300 . ?
C23 C22 1.372(4) . ?
C24 F0 1.303(15) . ?
C24 F4 1.323(15) . ?
C24 F5 1.235(16) . ?
C22 H22 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.324(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.410(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.370(4) . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.333(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.410(6) . ?
C20 H20 0.9300 . ?
C3 H3 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
C8 C7 C15 121.1(2) . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 C15 118.3(2) . . ?
C7 C8 C9 119.0(2) . . ?
C7 C8 C14 123.7(2) . . ?
C14 C8 C9 117.3(2) . . ?
C23 C18 C16 121.6(2) . . ?
C19 C18 C16 121.7(2) . . ?
C19 C18 C23 116.7(2) . . ?
C17 C16 C18 116.2(2) . . ?
C15 C16 C18 124.8(2) . . ?
C15 C16 C17 118.8(2) . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 C1 122.8(3) . . ?
C1 C6 C5 117.7(3) . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 C11 121.7(3) . . ?
C11 C9 C8 118.8(3) . . ?
N1 C17 C16 177.2(3) . . ?
C22 C21 C24 120.7(3) . . ?
C20 C21 C24 121.2(3) . . ?
C20 C21 C22 118.1(3) . . ?
C10 C5 C6 119.0(3) . . ?
C10 C5 C4 122.2(3) . . ?
C4 C5 C6 118.8(3) . . ?
C7 C15 H15 115.8 . . ?
C16 C15 C7 128.3(2) . . ?
C16 C15 H15 115.8 . . ?
C8 C14 H14 119.5 . . ?
C13 C14 C8 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C10 C5 122.5(3) . . ?
C9 C10 H10 118.8 . . ?
C5 C10 H10 118.8 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.8(3) . . ?
C2 C1 H1 119.6 . . ?
C18 C23 H23 119.1 . . ?
C22 C23 C18 121.7(3) . . ?
C22 C23 H23 119.1 . . ?
F2 C24 C21 113.5(3) . . ?
F3 C24 F2 104.1(3) . . ?
F3 C24 C21 113.4(3) . . ?
F1 C24 F2 105.2(3) . . ?
F1 C24 F3 106.5(3) . . ?
F1 C24 C21 113.3(3) . . ?
F0 C24 C21 108.1(9) . . ?
F0 C24 F4 107.0(17) . . ?
F4 C24 C21 107.1(9) . . ?
F5 C24 C21 111.9(11) . . ?
F5 C24 F0 115.4(18) . . ?
F5 C24 F4 107.0(18) . . ?
C21 C22 C23 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C9 C11 H11 119.2 . . ?
C12 C11 C9 121.6(3) . . ?
C12 C11 H11 119.2 . . ?
C14 C13 H13 119.4 . . ?
C14 C13 C12 121.1(3) . . ?
C12 C13 H13 119.4 . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.3(3) . . ?
C20 C19 H19 119.3 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C5 C4 H4 119.1 . . ?
C3 C4 C5 121.8(4) . . ?
C3 C4 H4 119.1 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C8 C9 C10 0.9(3) . . . . ?
C7 C8 C9 C11 -179.8(2) . . . . ?
C7 C8 C14 C13 -178.5(3) . . . . ?
C7 C6 C5 C10 -0.2(3) . . . . ?
C7 C6 C5 C4 179.5(2) . . . . ?
C7 C6 C1 C2 -179.0(2) . . . . ?
C8 C7 C6 C5 2.4(3) . . . . ?
C8 C7 C6 C1 -178.0(2) . . . . ?
C8 C7 C15 C16 -62.7(4) . . . . ?
C8 C9 C10 C5 1.4(4) . . . . ?
C8 C9 C11 C12 -2.4(4) . . . . ?
C8 C14 C13 C12 -0.9(4) . . . . ?
C18 C16 C15 C7 -180.0(2) . . . . ?
C18 C23 C22 C21 -0.5(5) . . . . ?
C18 C19 C20 C21 0.0(6) . . . . ?
C16 C18 C23 C22 -178.4(3) . . . . ?
C16 C18 C19 C20 178.7(3) . . . . ?
C6 C7 C8 C9 -2.7(3) . . . . ?
C6 C7 C8 C14 174.4(2) . . . . ?
C6 C7 C15 C16 121.7(3) . . . . ?
C6 C5 C10 C9 -1.8(4) . . . . ?
C6 C5 C4 C3 0.1(4) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C9 C8 C14 C13 -1.2(4) . . . . ?
C9 C11 C12 C13 0.2(5) . . . . ?
C17 C16 C15 C7 -3.0(4) . . . . ?
C5 C6 C1 C2 0.6(4) . . . . ?
C5 C4 C3 C2 -0.4(5) . . . . ?
C15 C7 C8 C9 -178.3(2) . . . . ?
C15 C7 C8 C14 -1.2(3) . . . . ?
C15 C7 C6 C5 178.1(2) . . . . ?
C15 C7 C6 C1 -2.3(3) . . . . ?
C14 C8 C9 C10 -176.5(2) . . . . ?
C14 C8 C9 C11 2.8(3) . . . . ?
C14 C13 C12 C11 1.5(5) . . . . ?
C10 C9 C11 C12 176.9(3) . . . . ?
C10 C5 C4 C3 179.7(3) . . . . ?
C1 C6 C5 C10 -179.8(2) . . . . ?
C1 C6 C5 C4 -0.2(3) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C23 C18 C16 C17 4.0(4) . . . . ?
C23 C18 C16 C15 -178.9(3) . . . . ?
C23 C18 C19 C20 -1.1(5) . . . . ?
C24 C21 C22 C23 178.4(3) . . . . ?
C24 C21 C20 C19 -178.1(3) . . . . ?
C22 C21 C24 F2 163.3(3) . . . . ?
C22 C21 C24 F3 44.8(5) . . . . ?
C22 C21 C24 F1 -76.8(5) . . . . ?
C22 C21 C24 F0 -139.5(15) . . . . ?
C22 C21 C24 F4 -24.6(16) . . . . ?
C22 C21 C24 F5 92.4(18) . . . . ?
C22 C21 C20 C19 1.0(5) . . . . ?
C11 C9 C10 C5 -177.9(3) . . . . ?
C19 C18 C16 C17 -175.8(3) . . . . ?
C19 C18 C16 C15 1.3(4) . . . . ?
C19 C18 C23 C22 1.4(4) . . . . ?
C4 C5 C10 C9 178.6(3) . . . . ?
C20 C21 C24 F2 -17.7(5) . . . . ?
C20 C21 C24 F3 -136.2(4) . . . . ?
C20 C21 C24 F1 102.2(4) . . . . ?
C20 C21 C24 F0 39.5(16) . . . . ?
C20 C21 C24 F4 154.4(16) . . . . ?
C20 C21 C24 F5 -88.6(18) . . . . ?
C20 C21 C22 C23 -0.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ov_wzc-2f_auto
_database_code_depnum_ccdc_archive 'CCDC 2429965'
loop_
_audit_author_name
_audit_author_address
'Zhengcheng Wang'
;Qingdao University
China
;
_audit_update_record             
;
2025-04-26 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_audit_creation_date             2025-04-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H13 F2 N'
_chemical_formula_sum            'C23 H13 F2 N'
_chemical_formula_weight         341.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   17.2254(6)
_cell_length_b                   7.4849(2)
_cell_length_c                   26.9940(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.221(3)
_cell_angle_gamma                90
_cell_volume                     3324.32(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3900
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.3040
_cell_measurement_theta_min      3.4200
_shelx_estimated_absorpt_T_max   0.829
_shelx_estimated_absorpt_T_min   0.750
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10154
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.762
_diffrn_reflns_theta_min         3.428
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2239
_reflns_number_total             3349
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.069
_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)+(0.0913P)²+1.2542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.1946
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C1(H1), C23(H23), C15(H15), C19(H19), C2(H2), C11(H11),
 C3(H3), C21(H21), C14(H14), C13(H13), C12(H12)
;
_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 0.85946(13) -0.0270(2) 0.25049(7) 0.1192(6) Uani 1 1 d . . . . .
F2 F 0.90871(19) 0.5610(3) 0.21190(9) 0.1648(10) Uani 1 1 d . . . . .
C9 C 0.64695(16) 0.5331(3) 0.46681(10) 0.0766(6) Uani 1 1 d . . . . .
C18 C 0.83615(12) 0.3857(3) 0.31394(8) 0.0683(6) Uani 1 1 d . . . . .
C16 C 0.80996(13) 0.4513(3) 0.35822(8) 0.0675(6) Uani 1 1 d . . . . .
C8 C 0.67425(16) 0.4667(3) 0.42522(9) 0.0742(6) Uani 1 1 d . . . . .
C10 C 0.70192(16) 0.5525(3) 0.51567(9) 0.0770(7) Uani 1 1 d . . . . .
H10 H 0.683441 0.598167 0.543021 0.092 Uiso 1 1 calc R U . . .
C4 C 0.83922(18) 0.5250(4) 0.57617(10) 0.0871(7) Uani 1 1 d . . . . .
H4 H 0.821005 0.571217 0.603571 0.104 Uiso 1 1 calc R U . . .
C1 C 0.89532(16) 0.3933(4) 0.49673(11) 0.0852(7) Uani 1 1 d . . . . .
H1 H 0.916018 0.348571 0.470224 0.102 Uiso 1 1 calc R U . . .
C6 C 0.81169(15) 0.4409(3) 0.48449(9) 0.0710(6) Uani 1 1 d . . . . .
C7 C 0.75704(15) 0.4237(3) 0.43460(9) 0.0719(6) Uani 1 1 d . . . . .
C5 C 0.78329(16) 0.5071(3) 0.52578(9) 0.0732(6) Uani 1 1 d . . . . .
C22 C 0.85975(16) 0.1494(4) 0.26104(9) 0.0853(7) Uani 1 1 d . . . . .
C23 C 0.83515(14) 0.2036(4) 0.30269(8) 0.0777(7) Uani 1 1 d . . . . .
H23 H 0.817842 0.118759 0.323390 0.093 Uiso 1 1 calc R U . . .
C15 C 0.78550(16) 0.3530(4) 0.39176(9) 0.0819(7) Uani 1 1 d . . . . .
H15 H 0.786336 0.226854 0.387944 0.098 Uiso 1 1 calc R U . . .
N1 N 0.8131(2) 0.7933(4) 0.36694(11) 0.1272(11) Uani 1 1 d . . . . .
C17 C 0.81123(17) 0.6394(4) 0.36430(9) 0.0848(7) Uani 1 1 d . . . . .
C19 C 0.86207(17) 0.5054(4) 0.28321(10) 0.0887(8) Uani 1 1 d . . . . .
H19 H 0.863522 0.629799 0.290343 0.106 Uiso 1 1 calc R U . . .
C2 C 0.94583(18) 0.4110(4) 0.54569(12) 0.0975(9) Uani 1 1 d . . . . .
H2 H 1.001294 0.377690 0.552976 0.117 Uiso 1 1 calc R U . . .
C11 C 0.56339(18) 0.5750(4) 0.45711(12) 0.0936(8) Uani 1 1 d . . . . .
H11 H 0.545099 0.621305 0.484465 0.112 Uiso 1 1 calc R U . . .
C3 C 0.9176(2) 0.4775(4) 0.58561(12) 0.0989(9) Uani 1 1 d . . . . .
H3 H 0.954033 0.489270 0.619613 0.119 Uiso 1 1 calc R U . . .
C21 C 0.88573(18) 0.2647(5) 0.23009(10) 0.0988(9) Uani 1 1 d . . . . .
H21 H 0.902864 0.223611 0.201708 0.119 Uiso 1 1 calc R U . . .
C14 C 0.61515(19) 0.4431(4) 0.37596(10) 0.0918(8) Uani 1 1 d . . . . .
H14 H 0.631534 0.398472 0.347659 0.110 Uiso 1 1 calc R U . . .
C13 C 0.5360(2) 0.4835(5) 0.36897(13) 0.1090(10) Uani 1 1 d . . . . .
H13 H 0.497563 0.466405 0.335868 0.131 Uiso 1 1 calc R U . . .
C20 C 0.8859(2) 0.4413(5) 0.24194(11) 0.1026(9) Uani 1 1 d . . . . .
C12 C 0.5097(2) 0.5507(5) 0.41021(14) 0.1109(10) Uani 1 1 d . . . . .
H12 H 0.453996 0.578687 0.404715 0.133 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 1.351(3) . ?
F2 C20 1.343(3) . ?
C9 C8 1.429(3) . ?
C9 C10 1.385(4) . ?
C9 C11 1.420(4) . ?
C18 C16 1.481(3) . ?
C18 C23 1.396(4) . ?
C18 C19 1.382(3) . ?
C16 C15 1.329(3) . ?
C16 C17 1.417(4) . ?
C8 C7 1.410(3) . ?
C8 C14 1.426(4) . ?
C10 H10 0.9500 . ?
C10 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.421(4) . ?
C4 C3 1.346(4) . ?
C1 H1 0.9500 . ?
C1 C6 1.425(4) . ?
C1 C2 1.357(4) . ?
C6 C7 1.402(3) . ?
C6 C5 1.432(3) . ?
C7 C15 1.481(3) . ?
C22 C23 1.375(3) . ?
C22 C21 1.365(4) . ?
C23 H23 0.9500 . ?
C15 H15 0.9500 . ?
N1 C17 1.154(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.341(5) . ?
C3 H3 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.360(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.355(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.412(5) . ?
C12 H12 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
C10 C9 C8 119.6(2) . . ?
C10 C9 C11 121.5(2) . . ?
C11 C9 C8 118.9(3) . . ?
C23 C18 C16 120.8(2) . . ?
C19 C18 C16 120.0(2) . . ?
C19 C18 C23 119.2(2) . . ?
C15 C16 C18 126.9(2) . . ?
C15 C16 C17 118.0(2) . . ?
C17 C16 C18 115.16(19) . . ?
C7 C8 C9 119.3(2) . . ?
C7 C8 C14 123.0(2) . . ?
C14 C8 C9 117.7(2) . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C5 121.8(2) . . ?
C5 C10 H10 119.1 . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.9(3) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 121.0(2) . . ?
C1 C6 C5 117.5(2) . . ?
C7 C6 C1 123.0(2) . . ?
C7 C6 C5 119.5(2) . . ?
C8 C7 C15 119.5(2) . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 C15 120.0(2) . . ?
C10 C5 C4 121.6(2) . . ?
C10 C5 C6 119.3(2) . . ?
C4 C5 C6 119.1(2) . . ?
F1 C22 C23 118.5(3) . . ?
F1 C22 C21 118.0(2) . . ?
C21 C22 C23 123.4(3) . . ?
C18 C23 H23 120.7 . . ?
C22 C23 C18 118.6(2) . . ?
C22 C23 H23 120.7 . . ?
C16 C15 C7 125.4(2) . . ?
C16 C15 H15 117.3 . . ?
C7 C15 H15 117.3 . . ?
N1 C17 C16 176.6(2) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 119.0(3) . . ?
C20 C19 H19 120.5 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.1(3) . . ?
C3 C2 H2 119.4 . . ?
C9 C11 H11 119.3 . . ?
C12 C11 C9 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C22 C21 H21 121.7 . . ?
C20 C21 C22 116.6(2) . . ?
C20 C21 H21 121.7 . . ?
C8 C14 H14 119.5 . . ?
C13 C14 C8 120.9(3) . . ?
C13 C14 H14 119.5 . . ?
C14 C13 H13 119.5 . . ?
C14 C13 C12 120.9(3) . . ?
C12 C13 H13 119.5 . . ?
F2 C20 C19 117.7(3) . . ?
F2 C20 C21 119.1(3) . . ?
C21 C20 C19 123.2(3) . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?

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 C22 C23 C18 179.4(2) . . . . ?
F1 C22 C21 C20 -179.5(3) . . . . ?
C9 C8 C7 C6 1.8(3) . . . . ?
C9 C8 C7 C15 179.4(2) . . . . ?
C9 C8 C14 C13 0.4(4) . . . . ?
C9 C10 C5 C4 -179.1(2) . . . . ?
C9 C10 C5 C6 1.0(3) . . . . ?
C9 C11 C12 C13 -0.6(5) . . . . ?
C18 C16 C15 C7 -177.8(2) . . . . ?
C18 C19 C20 F2 178.3(3) . . . . ?
C18 C19 C20 C21 -0.6(5) . . . . ?
C16 C18 C23 C22 179.7(2) . . . . ?
C16 C18 C19 C20 -179.7(2) . . . . ?
C8 C9 C10 C5 -0.8(4) . . . . ?
C8 C9 C11 C12 1.2(4) . . . . ?
C8 C7 C15 C16 87.9(3) . . . . ?
C8 C14 C13 C12 0.2(5) . . . . ?
C10 C9 C8 C7 -0.6(3) . . . . ?
C10 C9 C8 C14 178.0(2) . . . . ?
C10 C9 C11 C12 -177.8(3) . . . . ?
C1 C6 C7 C8 177.6(2) . . . . ?
C1 C6 C7 C15 0.1(3) . . . . ?
C1 C6 C5 C10 -179.1(2) . . . . ?
C1 C6 C5 C4 1.1(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C6 C7 C15 C16 -94.5(3) . . . . ?
C7 C8 C14 C13 178.9(3) . . . . ?
C7 C6 C5 C10 0.2(3) . . . . ?
C7 C6 C5 C4 -179.7(2) . . . . ?
C5 C4 C3 C2 0.7(4) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C5 C6 C7 C15 -179.1(2) . . . . ?
C22 C21 C20 F2 -178.2(3) . . . . ?
C22 C21 C20 C19 0.6(5) . . . . ?
C23 C18 C16 C15 1.7(4) . . . . ?
C23 C18 C16 C17 -177.9(2) . . . . ?
C23 C18 C19 C20 0.4(4) . . . . ?
C23 C22 C21 C20 -0.6(4) . . . . ?
C17 C16 C15 C7 1.7(4) . . . . ?
C19 C18 C16 C15 -178.3(2) . . . . ?
C19 C18 C16 C17 2.2(3) . . . . ?
C19 C18 C23 C22 -0.3(3) . . . . ?
C2 C1 C6 C7 -179.5(2) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C11 C9 C8 C7 -179.6(2) . . . . ?
C11 C9 C8 C14 -1.0(4) . . . . ?
C11 C9 C10 C5 178.2(2) . . . . ?
C3 C4 C5 C10 178.8(2) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
C21 C22 C23 C18 0.4(4) . . . . ?
C14 C8 C7 C6 -176.7(2) . . . . ?
C14 C8 C7 C15 0.9(4) . . . . ?
C14 C13 C12 C11 -0.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ov_z-3an2pa_autored
_database_code_depnum_ccdc_archive 'CCDC 2469131'
loop_
_audit_author_name
_audit_author_address
'Zhengcheng Wang'
;Qingdao University
China
;
_audit_update_record             
;
2025-07-02 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 N'
_chemical_formula_sum            'C23 H15 N'
_chemical_formula_weight         305.36
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   18.3518(3)
_cell_length_b                   5.28900(10)
_cell_length_c                   17.3164(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.188(2)
_cell_angle_gamma                90
_cell_volume                     1587.40(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    149.99(10)
_cell_measurement_reflns_used    7521
_cell_measurement_theta_min      2.5420
_cell_measurement_theta_max      76.7410
_shelx_estimated_absorpt_T_max   0.871
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9726
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.972
_diffrn_reflns_theta_min         2.549
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2866
_reflns_number_total             3189
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.066
_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)+(0.0533P)²+0.2545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.0997
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C23(H23), C7(H7), C11(H11), C4(H4), C20(H20), C22(H22),
 C21(H21), C12(H12), C3(H3), C14(H14), C1(H1), C13(H13), C2(H2)
;
_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
N1 N 0.34422(6) 0.5288(2) 0.45090(6) 0.0421(3) Uani 1 1 d . . . . .
C18 C 0.42022(6) 0.05732(18) 0.59917(5) 0.0251(2) Uani 1 1 d . . . . .
C10 C 0.22028(5) 0.36878(19) 0.56713(6) 0.0258(2) Uani 1 1 d . . . . .
C5 C 0.20708(5) 0.55108(19) 0.62060(6) 0.0260(2) Uani 1 1 d . . . . .
C9 C 0.16642(6) 0.33475(19) 0.48811(6) 0.0267(2) Uani 1 1 d . . . . .
C6 C 0.14084(6) 0.7121(2) 0.59300(6) 0.0284(2) Uani 1 1 d . . . . .
C17 C 0.34641(6) 0.3896(2) 0.50213(6) 0.0287(2) Uani 1 1 d . . . . .
C15 C 0.29058(6) 0.21191(19) 0.59698(6) 0.0272(2) Uani 1 1 d . . . . .
H15 H 0.294230 0.099281 0.640829 0.033 Uiso 1 1 calc R U . . .
C16 C 0.34984(5) 0.21446(18) 0.56755(5) 0.0252(2) Uani 1 1 d . . . . .
C19 C 0.41894(6) -0.16329(19) 0.64309(6) 0.0285(2) Uani 1 1 d . . . . .
H19 H 0.372415 -0.213748 0.651456 0.034 Uiso 1 1 calc R U . . .
C23 C 0.48894(6) 0.1261(2) 0.58674(6) 0.0283(2) Uani 1 1 d . . . . .
H23 H 0.490737 0.274562 0.556551 0.034 Uiso 1 1 calc R U . . .
C8 C 0.09947(6) 0.4940(2) 0.46205(6) 0.0290(2) Uani 1 1 d . . . . .
C7 C 0.08902(6) 0.6797(2) 0.51425(6) 0.0314(2) Uani 1 1 d . . . . .
H7 H 0.045325 0.787606 0.495694 0.038 Uiso 1 1 calc R U . . .
C11 C 0.17376(6) 0.1412(2) 0.43333(6) 0.0315(2) Uani 1 1 d . . . . .
H11 H 0.217307 0.032157 0.449515 0.038 Uiso 1 1 calc R U . . .
C4 C 0.25839(6) 0.5843(2) 0.70247(6) 0.0301(2) Uani 1 1 d . . . . .
H4 H 0.302459 0.478554 0.722322 0.036 Uiso 1 1 calc R U . . .
C20 C 0.48453(6) -0.3088(2) 0.67447(6) 0.0322(2) Uani 1 1 d . . . . .
H20 H 0.483064 -0.457401 0.704732 0.039 Uiso 1 1 calc R U . . .
C22 C 0.55462(6) -0.0210(2) 0.61817(6) 0.0330(2) Uani 1 1 d . . . . .
H22 H 0.601217 0.027787 0.609654 0.040 Uiso 1 1 calc R U . . .
C21 C 0.55262(6) -0.2383(2) 0.66187(6) 0.0334(2) Uani 1 1 d . . . . .
H21 H 0.597669 -0.338943 0.683183 0.040 Uiso 1 1 calc R U . . .
C12 C 0.11931(7) 0.1108(2) 0.35837(7) 0.0355(3) Uani 1 1 d . . . . .
H12 H 0.125315 -0.018925 0.323000 0.043 Uiso 1 1 calc R U . . .
C3 C 0.24522(6) 0.7645(2) 0.75239(6) 0.0354(3) Uani 1 1 d . . . . .
H3 H 0.279776 0.781628 0.806689 0.042 Uiso 1 1 calc R U . . .
C14 C 0.04425(6) 0.4557(2) 0.38246(6) 0.0357(3) Uani 1 1 d . . . . .
H14 H 0.000138 0.561954 0.364315 0.043 Uiso 1 1 calc R U . . .
C1 C 0.13009(6) 0.9012(2) 0.64717(7) 0.0353(3) Uani 1 1 d . . . . .
H1 H 0.086845 1.011039 0.628929 0.042 Uiso 1 1 calc R U . . .
C13 C 0.05380(6) 0.2709(2) 0.33265(6) 0.0381(3) Uani 1 1 d . . . . .
H13 H 0.016378 0.248324 0.280131 0.046 Uiso 1 1 calc R U . . .
C2 C 0.18048(7) 0.9269(2) 0.72418(7) 0.0379(3) Uani 1 1 d . . . . .
H2 H 0.172319 1.054067 0.759230 0.045 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
N1 C17 1.1435(13) . ?
C18 C16 1.4812(13) . ?
C18 C19 1.3972(14) . ?
C18 C23 1.3955(14) . ?
C10 C5 1.4118(14) . ?
C10 C9 1.4117(14) . ?
C10 C15 1.4770(13) . ?
C5 C6 1.4314(14) . ?
C5 C4 1.4318(14) . ?
C9 C8 1.4346(14) . ?
C9 C11 1.4317(14) . ?
C6 C7 1.3931(15) . ?
C6 C1 1.4287(15) . ?
C17 C16 1.4486(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.3442(14) . ?
C19 H19 0.9500 . ?
C19 C20 1.3808(15) . ?
C23 H23 0.9500 . ?
C23 C22 1.3865(15) . ?
C8 C7 1.3903(15) . ?
C8 C14 1.4316(14) . ?
C7 H7 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.3626(15) . ?
C4 H4 0.9500 . ?
C4 C3 1.3607(15) . ?
C20 H20 0.9500 . ?
C20 C21 1.3881(16) . ?
C22 H22 0.9500 . ?
C22 C21 1.3833(16) . ?
C21 H21 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.4174(17) . ?
C3 H3 0.9500 . ?
C3 C2 1.4164(17) . ?
C14 H14 0.9500 . ?
C14 C13 1.3524(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.3569(16) . ?
C13 H13 0.9500 . ?
C2 H2 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
C19 C18 C16 120.07(9) . . ?
C23 C18 C16 121.28(9) . . ?
C23 C18 C19 118.64(9) . . ?
C5 C10 C15 118.20(8) . . ?
C9 C10 C5 120.43(9) . . ?
C9 C10 C15 121.35(9) . . ?
C10 C5 C6 119.81(9) . . ?
C10 C5 C4 122.31(9) . . ?
C6 C5 C4 117.88(9) . . ?
C10 C9 C8 118.98(9) . . ?
C10 C9 C11 123.03(9) . . ?
C11 C9 C8 117.95(9) . . ?
C7 C6 C5 119.04(9) . . ?
C7 C6 C1 122.11(10) . . ?
C1 C6 C5 118.85(9) . . ?
N1 C17 C16 179.45(13) . . ?
C10 C15 H15 117.1 . . ?
C16 C15 C10 125.75(9) . . ?
C16 C15 H15 117.1 . . ?
C17 C16 C18 117.15(8) . . ?
C15 C16 C18 124.76(9) . . ?
C15 C16 C17 118.05(9) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.74(9) . . ?
C20 C19 H19 119.6 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.42(10) . . ?
C22 C23 H23 119.8 . . ?
C7 C8 C9 119.82(9) . . ?
C7 C8 C14 121.36(10) . . ?
C14 C8 C9 118.82(10) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.84(9) . . ?
C8 C7 H7 119.1 . . ?
C9 C11 H11 119.5 . . ?
C12 C11 C9 121.08(10) . . ?
C12 C11 H11 119.5 . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.24(10) . . ?
C3 C4 H4 119.4 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.12(10) . . ?
C21 C20 H20 119.9 . . ?
C23 C22 H22 119.8 . . ?
C21 C22 C23 120.32(10) . . ?
C21 C22 H22 119.8 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.75(10) . . ?
C22 C21 H21 120.1 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.64(10) . . ?
C13 C12 H12 119.7 . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.65(10) . . ?
C2 C3 H3 119.7 . . ?
C8 C14 H14 119.4 . . ?
C13 C14 C8 121.13(10) . . ?
C13 C14 H14 119.4 . . ?
C6 C1 H1 119.4 . . ?
C2 C1 C6 121.27(10) . . ?
C2 C1 H1 119.4 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.38(10) . . ?
C14 C13 H13 119.8 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.09(10) . . ?
C1 C2 H2 120.0 . . ?

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
C18 C19 C20 C21 -0.68(15) . . . . ?
C18 C23 C22 C21 0.33(15) . . . . ?
C10 C5 C6 C7 2.11(14) . . . . ?
C10 C5 C6 C1 -177.79(9) . . . . ?
C10 C5 C4 C3 178.75(9) . . . . ?
C10 C9 C8 C7 0.63(14) . . . . ?
C10 C9 C8 C14 -178.83(9) . . . . ?
C10 C9 C11 C12 178.23(9) . . . . ?
C10 C15 C16 C18 179.25(9) . . . . ?
C10 C15 C16 C17 1.61(15) . . . . ?
C5 C10 C9 C8 2.09(14) . . . . ?
C5 C10 C9 C11 -175.38(9) . . . . ?
C5 C10 C15 C16 -114.82(11) . . . . ?
C5 C6 C7 C8 0.63(15) . . . . ?
C5 C6 C1 C2 -1.28(16) . . . . ?
C5 C4 C3 C2 -0.74(16) . . . . ?
C9 C10 C5 C6 -3.47(14) . . . . ?
C9 C10 C5 C4 177.18(9) . . . . ?
C9 C10 C15 C16 66.70(14) . . . . ?
C9 C8 C7 C6 -2.00(15) . . . . ?
C9 C8 C14 C13 0.99(15) . . . . ?
C9 C11 C12 C13 0.04(16) . . . . ?
C6 C5 C4 C3 -0.61(15) . . . . ?
C6 C1 C2 C3 -0.07(17) . . . . ?
C15 C10 C5 C6 178.04(8) . . . . ?
C15 C10 C5 C4 -1.31(14) . . . . ?
C15 C10 C9 C8 -179.47(9) . . . . ?
C15 C10 C9 C11 3.06(15) . . . . ?
C16 C18 C19 C20 -178.58(9) . . . . ?
C16 C18 C23 C22 178.75(9) . . . . ?
C19 C18 C16 C17 -160.72(9) . . . . ?
C19 C18 C16 C15 21.62(14) . . . . ?
C19 C18 C23 C22 -0.62(14) . . . . ?
C19 C20 C21 C22 0.37(15) . . . . ?
C23 C18 C16 C17 19.92(13) . . . . ?
C23 C18 C16 C15 -157.75(10) . . . . ?
C23 C18 C19 C20 0.80(14) . . . . ?
C23 C22 C21 C20 -0.20(15) . . . . ?
C8 C9 C11 C12 0.73(15) . . . . ?
C8 C14 C13 C12 -0.22(17) . . . . ?
C7 C6 C1 C2 178.83(10) . . . . ?
C7 C8 C14 C13 -178.45(10) . . . . ?
C11 C9 C8 C7 178.23(9) . . . . ?
C11 C9 C8 C14 -1.22(14) . . . . ?
C11 C12 C13 C14 -0.31(17) . . . . ?
C4 C5 C6 C7 -178.51(9) . . . . ?
C4 C5 C6 C1 1.59(14) . . . . ?
C4 C3 C2 C1 1.10(17) . . . . ?
C14 C8 C7 C6 177.44(10) . . . . ?
C1 C6 C7 C8 -179.47(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
