# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 2280421'
loop_
_audit_author_name
_audit_author_address
'Jieyu Tang'
;Dalian University of Technology
China
;
_audit_update_record             
;
2023-07-10 deposited with the CCDC.	2023-11-29 downloaded from the CCDC.
;
_audit_creation_date             2023-06-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H19 N2 O4'
_chemical_formula_sum            'C31 H19 N2 O4'
_chemical_formula_weight         483.48
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6346(8)
_cell_length_b                   22.406(3)
_cell_length_c                   12.3194(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.684(3)
_cell_angle_gamma                90
_cell_volume                     2294.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2395
_cell_measurement_temperature    294.8
_cell_measurement_theta_max      21.659
_cell_measurement_theta_min      2.501
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1470 before and 0.0805 after correction.
The Ratio of minimum to maximum transmission is 0.8829.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16901
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.016
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         2.501
_diffrn_ambient_temperature      294.8
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2140
_reflns_number_total             4021
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0117(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4021
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.2042
_refine_ls_R_factor_gt           0.1254
_refine_ls_restrained_S_all      1.046
_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)+10.7092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2392
_refine_ls_wR_factor_ref         0.2784
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2A-C14 \\sim N2B-C19
 with sigma of 0.02
 N2A-C20 \\sim N2B-C20
 with sigma of 0.02
 N2A-C27 \\sim N2B-C27
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C20, N2B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C20, N2A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Fixed Sof: N2B(0.5) N2A(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C24(H24), C4(H4), C7(H7), C17(H17), C18(H18), C23(H23), C31(H31),
 C22(H22), C3(H3), C30(H30), C29(H29), C21(H21), C28(H28), C12(H12), C13(H13)
5.b Fitted hexagon refined as free rotating group:
 C14(C15,C16,C10,C12,C13)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.8725(6) 0.6224(2) 0.4399(4) 0.0529(14) Uani 1 1 d . . . . .
O2 O 0.7467(6) 0.5646(2) 0.5407(5) 0.0793(16) Uani 1 1 d . . . . .
O003 O 1.4455(6) 0.6238(2) 0.7805(5) 0.0844(17) Uani 1 1 d . . . . .
O1 O 0.9960(8) 0.6793(3) 0.3377(5) 0.100(2) Uani 1 1 d . . . . .
C5 C 1.0200(7) 0.6199(3) 0.5304(5) 0.0508(16) Uani 1 1 d . . . . .
C9 C 0.7371(8) 0.5931(3) 0.4541(6) 0.0559(17) Uani 1 1 d . . . . .
C6 C 1.1253(8) 0.5743(3) 0.5359(6) 0.0615(19) Uani 1 1 d . . . . .
H6 H 1.100424 0.543293 0.483913 0.074 Uiso 1 1 calc R U . . .
C2 C 1.3062(8) 0.6196(3) 0.6966(6) 0.0620(19) Uani 1 1 d . . . . .
C24 C 0.0057(8) 0.5396(3) -0.1952(6) 0.065(2) Uani 1 1 d . . . . .
H24 H -0.086811 0.541900 -0.254966 0.078 Uiso 1 1 calc R U . . .
C4 C 1.0550(8) 0.6651(3) 0.6074(6) 0.064(2) Uani 1 1 d . . . . .
H4 H 0.982633 0.696221 0.603617 0.077 Uiso 1 1 calc R U . . .
C8 C 0.8734(10) 0.6542(3) 0.3430(6) 0.068(2) Uani 1 1 d . . . . .
C7 C 1.2704(8) 0.5740(3) 0.6195(6) 0.064(2) Uani 1 1 d . . . . .
H7 H 1.343054 0.542962 0.623222 0.077 Uiso 1 1 calc R U . . .
C17 C 0.4505(9) 0.5716(4) 0.3758(9) 0.095(3) Uani 1 1 d . . . . .
H17 H 0.451262 0.551079 0.441564 0.115 Uiso 1 1 calc R U . . .
C11 C 0.5889(8) 0.5975(3) 0.3624(7) 0.065(2) Uani 1 1 d . . . . .
C19 C 0.3032(18) 0.6035(7) 0.1912(12) 0.163(9) Uani 1 1 d D . . . .
C18 C 0.3079(12) 0.5766(6) 0.2878(14) 0.152(7) Uani 1 1 d . . . . .
H18 H 0.213477 0.560529 0.297871 0.182 Uiso 1 1 calc R U . . .
C23 C 0.0995(9) 0.4891(3) -0.1809(6) 0.070(2) Uani 1 1 d . . . . .
H23 H 0.069541 0.457348 -0.230670 0.084 Uiso 1 1 calc R U . . .
C31 C -0.1110(9) 0.7297(4) -0.0909(7) 0.075(2) Uani 1 1 d . . . . .
H31 H -0.203664 0.728787 -0.150736 0.089 Uiso 1 1 calc R U . . .
C22 C 0.2359(9) 0.4853(3) -0.0943(7) 0.075(2) Uani 1 1 d . . . . .
H22 H 0.299549 0.451231 -0.084767 0.090 Uiso 1 1 calc R U . . .
C3 C 1.1975(9) 0.6642(3) 0.6903(7) 0.080(2) Uani 1 1 d . . . . .
H3 H 1.220213 0.694787 0.743364 0.096 Uiso 1 1 calc R U . . .
C30 C -0.0771(12) 0.7787(4) -0.0224(8) 0.090(3) Uani 1 1 d . . . . .
H30 H -0.146151 0.811318 -0.036621 0.108 Uiso 1 1 calc R U . . .
C29 C 0.0580(11) 0.7801(4) 0.0674(9) 0.093(3) Uani 1 1 d . . . . .
H29 H 0.080604 0.813320 0.114325 0.112 Uiso 1 1 calc R U . . .
C1 C 1.5594(9) 0.5772(4) 0.7881(8) 0.103(3) Uani 1 1 d . . . . .
H1A H 1.593158 0.575884 0.719975 0.154 Uiso 1 1 calc R U . . .
H1B H 1.511147 0.539751 0.798307 0.154 Uiso 1 1 calc R U . . .
H1C H 1.650974 0.584422 0.851055 0.154 Uiso 1 1 calc R U . . .
C21 C 0.2781(12) 0.5323(4) -0.0217(8) 0.125(4) Uani 1 1 d . . . . .
H21 H 0.371742 0.530320 0.037158 0.149 Uiso 1 1 calc R U . . .
C28 C 0.1590(11) 0.7316(4) 0.0865(10) 0.128(5) Uani 1 1 d . . . . .
H28 H 0.252589 0.732553 0.145521 0.154 Uiso 1 1 calc R U . . .
C27 C 0.1237(11) 0.6816(4) 0.0195(9) 0.142(5) Uani 1 1 d D . . . .
C26 C -0.0089(9) 0.6825(4) -0.0712(7) 0.082(3) Uani 1 1 d . . . . .
O3 O -0.0549(6) 0.6342(3) -0.1427(6) 0.116(3) Uani 1 1 d . . . . .
C25 C 0.0467(8) 0.5853(4) -0.1237(7) 0.076(2) Uani 1 1 d . . . . .
C20 C 0.1833(10) 0.5822(4) -0.0351(8) 0.111(3) Uani 1 1 d D . . . .
C14 C 0.4447(9) 0.6555(3) 0.0729(5) 0.182(10) Uani 1 1 d DG . . . .
C15 C 0.4453(6) 0.6284(3) 0.1744(6) 0.117(5) Uani 1 1 d G . . A .
C16 C 0.5854(7) 0.6275(2) 0.2625(4) 0.076(3) Uani 1 1 d G . . A .
C10 C 0.7249(6) 0.6537(2) 0.2491(4) 0.073(2) Uani 1 1 d G . . A .
C12 C 0.7243(9) 0.6809(2) 0.1476(5) 0.113(4) Uani 1 1 d G . . A .
H12 H 0.817575 0.698515 0.138625 0.136 Uiso 1 1 calc R U . . .
C13 C 0.5842(11) 0.6818(3) 0.0595(4) 0.161(8) Uani 1 1 d G . . A .
H13 H 0.583787 0.700001 -0.008478 0.193 Uiso 1 1 calc R U . . .
N2B N 0.1818(13) 0.6179(4) 0.0732(9) 0.068(3) Uani 0.5 1 d D . P A 2
N2A N 0.2642(12) 0.6460(5) -0.0022(9) 0.070(3) Uani 0.5 1 d D . P A 1


_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 C5 1.450(7) . ?
N1 C9 1.393(8) . ?
N1 C8 1.391(9) . ?
O2 C9 1.227(8) . ?
O003 C2 1.361(7) . ?
O003 C1 1.420(9) . ?
O1 C8 1.216(9) . ?
C5 C6 1.357(9) . ?
C5 C4 1.363(9) . ?
C9 C11 1.463(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(9) . ?
C2 C7 1.371(9) . ?
C2 C3 1.360(10) . ?
C24 H24 0.9300 . ?
C24 C23 1.374(9) . ?
C24 C25 1.335(9) . ?
C4 H4 0.9300 . ?
C4 C3 1.370(9) . ?
C8 C10 1.477(8) . ?
C7 H7 0.9300 . ?
C17 H17 0.9300 . ?
C17 C11 1.379(10) . ?
C17 C18 1.408(14) . ?
C11 C16 1.394(9) . ?
C19 C18 1.32(2) . ?
C19 C15 1.41(2) . ?
C19 N2B 1.579(13) . ?
C18 H18 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.361(10) . ?
C31 H31 0.9300 . ?
C31 C30 1.367(11) . ?
C31 C26 1.356(9) . ?
C22 H22 0.9300 . ?
C22 C21 1.364(10) . ?
C3 H3 0.9300 . ?
C30 H30 0.9300 . ?
C30 C29 1.373(12) . ?
C29 H29 0.9300 . ?
C29 C28 1.374(11) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C21 H21 0.9300 . ?
C21 C20 1.370(11) . ?
C28 H28 0.9300 . ?
C28 C27 1.375(11) . ?
C27 C26 1.367(11) . ?
C27 N2B 1.597(12) . ?
C27 N2A 1.535(12) . ?
C26 O3 1.385(9) . ?
O3 C25 1.383(8) . ?
C25 C20 1.375(10) . ?
C20 N2B 1.558(12) . ?
C20 N2A 1.595(12) . ?
C14 C15 1.3900 . ?
C14 C13 1.3900 . ?
C14 N2A 1.597(10) . ?
C15 C16 1.3900 . ?
C16 C10 1.3900 . ?
C10 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C13 1.3900 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C5 118.5(6) . . ?
C8 N1 C5 118.2(6) . . ?
C8 N1 C9 123.3(6) . . ?
C2 O003 C1 117.0(6) . . ?
C6 C5 N1 120.4(6) . . ?
C6 C5 C4 120.3(6) . . ?
C4 C5 N1 119.3(6) . . ?
N1 C9 C11 117.3(7) . . ?
O2 C9 N1 119.5(6) . . ?
O2 C9 C11 123.1(7) . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.8(7) . . ?
C7 C6 H6 120.1 . . ?
O003 C2 C7 124.4(7) . . ?
C3 C2 O003 116.6(7) . . ?
C3 C2 C7 119.1(6) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C25 C24 C23 120.3(7) . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.6(7) . . ?
C3 C4 H4 120.2 . . ?
N1 C8 C10 117.6(7) . . ?
O1 C8 N1 119.4(7) . . ?
O1 C8 C10 123.0(7) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 C6 119.9(7) . . ?
C2 C7 H7 120.0 . . ?
C11 C17 H17 120.7 . . ?
C11 C17 C18 118.7(11) . . ?
C18 C17 H17 120.7 . . ?
C17 C11 C9 119.0(8) . . ?
C17 C11 C16 119.7(7) . . ?
C16 C11 C9 121.3(6) . . ?
C18 C19 C15 119.6(11) . . ?
C18 C19 N2B 140.5(17) . . ?
C15 C19 N2B 99.9(13) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 C17 122.4(14) . . ?
C19 C18 H18 118.8 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.5(7) . . ?
C22 C23 H23 119.8 . . ?
C30 C31 H31 120.2 . . ?
C26 C31 H31 120.2 . . ?
C26 C31 C30 119.6(8) . . ?
C23 C22 H22 120.4 . . ?
C23 C22 C21 119.1(7) . . ?
C21 C22 H22 120.4 . . ?
C2 C3 C4 121.3(7) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C31 C30 H30 119.7 . . ?
C31 C30 C29 120.7(8) . . ?
C29 C30 H30 119.7 . . ?
C30 C29 H29 120.6 . . ?
C30 C29 C28 118.7(9) . . ?
C28 C29 H29 120.6 . . ?
O003 C1 H1A 109.5 . . ?
O003 C1 H1B 109.5 . . ?
O003 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C22 C21 H21 119.8 . . ?
C22 C21 C20 120.4(8) . . ?
C20 C21 H21 119.8 . . ?
C29 C28 H28 119.5 . . ?
C29 C28 C27 121.0(9) . . ?
C27 C28 H28 119.5 . . ?
C28 C27 N2B 119.1(9) . . ?
C28 C27 N2A 118.1(9) . . ?
C26 C27 C28 118.6(8) . . ?
C26 C27 N2B 116.9(8) . . ?
C26 C27 N2A 113.1(8) . . ?
C31 C26 C27 121.3(8) . . ?
C31 C26 O3 115.8(7) . . ?
C27 C26 O3 122.7(7) . . ?
C25 O3 C26 116.9(6) . . ?
C24 C25 O3 116.9(6) . . ?
C24 C25 C20 120.2(7) . . ?
C20 C25 O3 122.9(7) . . ?
C21 C20 C25 119.5(8) . . ?
C21 C20 N2B 117.3(8) . . ?
C21 C20 N2A 119.7(8) . . ?
C25 C20 N2B 116.8(8) . . ?
C25 C20 N2A 112.3(8) . . ?
C15 C14 C13 120.0 . . ?
C15 C14 N2A 103.2(7) . . ?
C13 C14 N2A 136.8(7) . . ?
C14 C15 C19 120.8(8) . . ?
C14 C15 C16 120.0 . . ?
C16 C15 C19 119.1(8) . . ?
C15 C16 C11 120.2(5) . . ?
C10 C16 C11 119.7(5) . . ?
C10 C16 C15 120.0 . . ?
C16 C10 C8 120.5(5) . . ?
C16 C10 C12 120.0 . . ?
C12 C10 C8 119.5(5) . . ?
C10 C12 H12 120.0 . . ?
C10 C12 C13 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C19 N2B C27 128.3(9) . . ?
C20 N2B C19 121.8(8) . . ?
C20 N2B C27 100.3(8) . . ?
C27 N2A C20 101.4(8) . . ?
C27 N2A C14 121.6(8) . . ?
C20 N2A C14 124.0(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
N1 C5 C6 C7 176.5(6) . . . . ?
N1 C5 C4 C3 -177.2(7) . . . . ?
N1 C9 C11 C17 -176.8(6) . . . . ?
N1 C9 C11 C16 3.2(10) . . . . ?
N1 C8 C10 C16 6.3(8) . . . . ?
N1 C8 C10 C12 -175.0(5) . . . . ?
O2 C9 C11 C17 3.8(11) . . . . ?
O2 C9 C11 C16 -176.2(7) . . . . ?
O003 C2 C7 C6 -179.1(7) . . . . ?
O003 C2 C3 C4 178.4(7) . . . . ?
O1 C8 C10 C16 -175.9(7) . . . . ?
O1 C8 C10 C12 2.8(10) . . . . ?
C5 N1 C9 O2 -2.0(10) . . . . ?
C5 N1 C9 C11 178.6(6) . . . . ?
C5 N1 C8 O1 -1.0(11) . . . . ?
C5 N1 C8 C10 176.8(6) . . . . ?
C5 C6 C7 C2 0.4(11) . . . . ?
C5 C4 C3 C2 1.0(13) . . . . ?
C9 N1 C5 C6 87.7(8) . . . . ?
C9 N1 C5 C4 -94.9(8) . . . . ?
C9 N1 C8 O1 179.0(7) . . . . ?
C9 N1 C8 C10 -3.2(10) . . . . ?
C9 C11 C16 C15 176.5(5) . . . . ?
C9 C11 C16 C10 -0.1(8) . . . . ?
C6 C5 C4 C3 0.2(11) . . . . ?
C24 C23 C22 C21 0.2(14) . . . . ?
C24 C25 C20 C21 1.0(16) . . . . ?
C24 C25 C20 N2B -150.2(9) . . . . ?
C24 C25 C20 N2A 148.9(9) . . . . ?
C4 C5 C6 C7 -0.9(11) . . . . ?
C8 N1 C5 C6 -92.3(8) . . . . ?
C8 N1 C5 C4 85.1(8) . . . . ?
C8 N1 C9 O2 178.0(7) . . . . ?
C8 N1 C9 C11 -1.4(10) . . . . ?
C8 C10 C12 C13 -178.7(5) . . . . ?
C7 C2 C3 C4 -1.4(13) . . . . ?
C17 C11 C16 C15 -3.5(9) . . . . ?
C17 C11 C16 C10 179.9(5) . . . . ?
C11 C17 C18 C19 2.6(18) . . . . ?
C11 C16 C10 C8 -4.7(7) . . . . ?
C11 C16 C10 C12 176.6(6) . . . . ?
C19 C15 C16 C11 5.9(8) . . . . ?
C19 C15 C16 C10 -177.5(8) . . . . ?
C18 C17 C11 C9 179.3(8) . . . . ?
C18 C17 C11 C16 -0.7(12) . . . . ?
C18 C19 C15 C14 178.4(11) . . . . ?
C18 C19 C15 C16 -4.1(17) . . . . ?
C18 C19 N2B C27 118(2) . . . . ?
C18 C19 N2B C20 -103(2) . . . . ?
C23 C24 C25 O3 -179.1(8) . . . . ?
C23 C24 C25 C20 0.0(14) . . . . ?
C23 C22 C21 C20 0.8(17) . . . . ?
C31 C30 C29 C28 0.5(15) . . . . ?
C31 C26 O3 C25 -179.5(8) . . . . ?
C22 C21 C20 C25 -1.4(18) . . . . ?
C22 C21 C20 N2B 149.7(10) . . . . ?
C22 C21 C20 N2A -146.9(11) . . . . ?
C3 C2 C7 C6 0.7(12) . . . . ?
C30 C31 C26 C27 3.3(15) . . . . ?
C30 C31 C26 O3 178.2(8) . . . . ?
C30 C29 C28 C27 -2.0(18) . . . . ?
C29 C28 C27 C26 4.2(19) . . . . ?
C29 C28 C27 N2B -149.0(11) . . . . ?
C29 C28 C27 N2A 147.0(11) . . . . ?
C1 O003 C2 C7 -0.5(11) . . . . ?
C1 O003 C2 C3 179.7(8) . . . . ?
C21 C20 N2B C19 9.2(17) . . . . ?
C21 C20 N2B C27 157.7(10) . . . . ?
C21 C20 N2A C27 -156.5(10) . . . . ?
C21 C20 N2A C14 -15.2(16) . . . . ?
C28 C27 C26 C31 -4.8(18) . . . . ?
C28 C27 C26 O3 -179.3(11) . . . . ?
C28 C27 N2B C19 -12(2) . . . . ?
C28 C27 N2B C20 -157.2(10) . . . . ?
C28 C27 N2A C20 157.7(11) . . . . ?
C28 C27 N2A C14 15.2(17) . . . . ?
C27 C26 O3 C25 -4.8(15) . . . . ?
C26 C31 C30 C29 -1.1(14) . . . . ?
C26 C27 N2B C19 -165.2(13) . . . . ?
C26 C27 N2B C20 49.2(12) . . . . ?
C26 C27 N2A C20 -57.5(12) . . . . ?
C26 C27 N2A C14 160.0(10) . . . . ?
C26 O3 C25 C24 -177.5(8) . . . . ?
C26 O3 C25 C20 3.5(14) . . . . ?
O3 C25 C20 C21 180.0(10) . . . . ?
O3 C25 C20 N2B 28.8(14) . . . . ?
O3 C25 C20 N2A -32.1(14) . . . . ?
C25 C24 C23 C22 -0.6(13) . . . . ?
C25 C20 N2B C19 161.0(13) . . . . ?
C25 C20 N2B C27 -50.4(11) . . . . ?
C25 C20 N2A C27 55.7(11) . . . . ?
C25 C20 N2A C14 -163.1(9) . . . . ?
C14 C15 C16 C11 -176.6(6) . . . . ?
C14 C15 C16 C10 0.0 . . . . ?
C15 C19 C18 C17 0(2) . . . . ?
C15 C19 N2B C27 -64.6(15) . . . . ?
C15 C19 N2B C20 74.6(13) . . . . ?
C15 C14 C13 C12 0.0 . . . . ?
C15 C14 N2A C27 73.4(11) . . . . ?
C15 C14 N2A C20 -60.6(10) . . . . ?
C15 C16 C10 C8 178.7(5) . . . . ?
C15 C16 C10 C12 0.0 . . . . ?
C16 C10 C12 C13 0.0 . . . . ?
C10 C12 C13 C14 0.0 . . . . ?
C13 C14 C15 C19 177.4(8) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C13 C14 N2A C27 -106.9(10) . . . . ?
C13 C14 N2A C20 119.1(9) . . . . ?
N2B C19 C18 C17 177.5(12) . . . . ?
N2B C19 C15 C14 0.0(10) . . . . ?
N2B C19 C15 C16 177.4(5) . . . . ?
N2B C27 C26 C31 148.9(9) . . . . ?
N2B C27 C26 O3 -25.5(16) . . . . ?
N2A C27 C26 C31 -149.4(9) . . . . ?
N2A C27 C26 O3 36.1(15) . . . . ?
N2A C14 C15 C19 -2.8(8) . . . . ?
N2A C14 C15 C16 179.8(5) . . . . ?
N2A C14 C13 C12 -179.7(7) . . . . ?

_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_2
_database_code_depnum_ccdc_archive 'CCDC 2280423'
loop_
_audit_author_name
_audit_author_address
'Jieyu Tang'
;Dalian University of Technology
China
;
_audit_update_record             
;
2023-07-10 deposited with the CCDC.	2023-11-29 downloaded from the CCDC.
;
_audit_creation_date             2022-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H17 F N2 O3'
_chemical_formula_sum            'C30 H17 F N2 O3'
_chemical_formula_weight         472.45
_chemical_absolute_configuration ?
_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 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.5160(6)
_cell_length_b                   12.9592(7)
_cell_length_c                   13.5707(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2201.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3154
_cell_measurement_temperature    294.8
_cell_measurement_theta_max      24.56
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5034
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1381 before and 0.0710 after correction.
The Ratio of minimum to maximum transmission is 0.6755.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12319
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.056
_diffrn_reflns_theta_max         25.056
_diffrn_reflns_theta_min         2.262
_diffrn_ambient_temperature      294.8
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                2820
_reflns_number_total             3832
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 943 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         3832
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.040
_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)+(0.0437P)²+0.1070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1091
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.8525(3) 0.6453(3) 0.4797(3) 0.0621(10) Uani 1 1 d . . . . .
H1 H 0.864(3) 0.578(4) 0.451(3) 0.083(14) Uiso 1 1 d . . . . .
C2 C 0.9045(4) 0.7287(4) 0.4359(4) 0.0736(13) Uani 1 1 d . . . . .
H2 H 0.946(4) 0.716(4) 0.379(4) 0.097(17) Uiso 1 1 d . . . . .
C3 C 0.8942(4) 0.8253(4) 0.4761(4) 0.0758(14) Uani 1 1 d . . . . .
H3 H 0.932(4) 0.889(4) 0.446(4) 0.101(15) Uiso 1 1 d . . . . .
C4 C 0.8313(4) 0.8405(3) 0.5572(4) 0.0722(13) Uani 1 1 d . . . . .
H4 H 0.817(4) 0.906(4) 0.586(4) 0.104(17) Uiso 1 1 d . . . . .
C5 C 0.7787(3) 0.7585(3) 0.5998(3) 0.0620(10) Uani 1 1 d . . . . .
C6 C 0.7903(3) 0.6592(3) 0.5617(3) 0.0537(9) Uani 1 1 d . . . . .
C7 C 0.6645(3) 0.5987(3) 0.6842(3) 0.0551(9) Uani 1 1 d . . . . .
C8 C 0.6549(3) 0.6998(3) 0.7188(3) 0.0616(10) Uani 1 1 d . . . . .
C9 C 0.5868(4) 0.7246(4) 0.7932(4) 0.0745(13) Uani 1 1 d . . . . .
H9 H 0.579(4) 0.796(4) 0.816(4) 0.106(17) Uiso 1 1 d . . . . .
C10 C 0.5238(4) 0.6498(5) 0.8363(4) 0.0845(16) Uani 1 1 d . . . . .
H10 H 0.473(4) 0.667(4) 0.891(3) 0.090(15) Uiso 1 1 d . . . . .
C11 C 0.5309(4) 0.5492(5) 0.8027(4) 0.0814(14) Uani 1 1 d . . . . .
H11 H 0.489(5) 0.494(5) 0.831(5) 0.14(2) Uiso 1 1 d . . . . .
C12 C 0.6005(4) 0.5241(4) 0.7275(3) 0.0685(11) Uani 1 1 d . . . . .
H12 H 0.609(3) 0.453(4) 0.699(3) 0.087(14) Uiso 1 1 d . . . . .
C13 C 0.7442(3) 0.4742(3) 0.5697(3) 0.0522(9) Uani 1 1 d . . . . .
C14 C 0.8127(3) 0.4058(3) 0.6126(3) 0.0585(10) Uani 1 1 d . . . . .
H14 H 0.862(3) 0.423(3) 0.664(3) 0.078(13) Uiso 1 1 d . . . . .
C15 C 0.8174(3) 0.3030(3) 0.5797(3) 0.0562(9) Uani 1 1 d . . . . .
H15 H 0.870(3) 0.254(3) 0.606(2) 0.053(10) Uiso 1 1 d . . . . .
C16 C 0.7512(3) 0.2709(3) 0.5054(3) 0.0461(8) Uani 1 1 d . . . . .
C17 C 0.6823(3) 0.3413(2) 0.4581(2) 0.0432(8) Uani 1 1 d . . . . .
C18 C 0.6790(3) 0.4459(2) 0.4897(2) 0.0465(8) Uani 1 1 d . . . . .
C19 C 0.6112(3) 0.5151(3) 0.4379(3) 0.0542(9) Uani 1 1 d . . . . .
H19 H 0.614(3) 0.590(3) 0.458(3) 0.070(12) Uiso 1 1 d . . . . .
C20 C 0.5524(3) 0.4829(3) 0.3605(3) 0.0606(10) Uani 1 1 d . . . . .
H20 H 0.507(4) 0.533(3) 0.325(3) 0.079(12) Uiso 1 1 d . . . . .
C21 C 0.5534(3) 0.3803(3) 0.3313(3) 0.0571(10) Uani 1 1 d . . . . .
H21 H 0.502(3) 0.349(3) 0.277(3) 0.063(11) Uiso 1 1 d . . . . .
C22 C 0.6164(3) 0.3091(3) 0.3800(3) 0.0465(8) Uani 1 1 d . . . . .
C23 C 0.6122(3) 0.2005(3) 0.3504(3) 0.0482(9) Uani 1 1 d . . . . .
C24 C 0.7539(3) 0.1615(3) 0.4747(3) 0.0515(9) Uani 1 1 d . . . . .
C25 C 0.7425(3) -0.1154(3) 0.2765(3) 0.0583(10) Uani 1 1 d . . . . .
H25 H 0.785(3) -0.139(3) 0.220(3) 0.072(12) Uiso 1 1 d . . . . .
C26 C 0.7430(3) -0.0111(3) 0.3006(3) 0.0572(10) Uani 1 1 d . . . . .
H26 H 0.793(3) 0.035(3) 0.265(3) 0.079(13) Uiso 1 1 d . . . . .
C27 C 0.6780(3) 0.0245(2) 0.3739(2) 0.0467(8) Uani 1 1 d . . . . .
C28 C 0.6101(3) -0.0411(3) 0.4227(3) 0.0590(10) Uani 1 1 d . . . . .
H28 H 0.559(3) -0.013(3) 0.477(3) 0.067(11) Uiso 1 1 d . . . . .
C29 C 0.6094(3) -0.1451(3) 0.3990(3) 0.0597(10) Uani 1 1 d . . . . .
H29 H 0.570(4) -0.189(4) 0.433(4) 0.089(15) Uiso 1 1 d . . . . .
C30 C 0.6762(3) -0.1787(3) 0.3281(3) 0.0523(9) Uani 1 1 d . . . . .
F1 F 0.6771(2) -0.28102(16) 0.30668(17) 0.0738(7) Uani 1 1 d . . . . .
N1 N 0.6814(2) 0.1329(2) 0.4011(2) 0.0478(7) Uani 1 1 d . . . . .
N2 N 0.7370(3) 0.5773(2) 0.6091(2) 0.0602(9) Uani 1 1 d . . . . .
O1 O 0.7168(3) 0.7786(2) 0.6811(3) 0.0882(10) Uani 1 1 d . . . . .
O2 O 0.5532(2) 0.1672(2) 0.2880(2) 0.0666(8) Uani 1 1 d . . . . .
O3 O 0.8131(3) 0.0982(2) 0.5108(2) 0.0827(9) 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
C1 H1 0.96(5) . ?
C1 C2 1.395(6) . ?
C1 C6 1.370(5) . ?
C2 H2 0.94(5) . ?
C2 C3 1.372(7) . ?
C3 H3 1.04(5) . ?
C3 C4 1.367(7) . ?
C4 H4 0.95(5) . ?
C4 C5 1.378(6) . ?
C5 C6 1.394(5) . ?
C5 O1 1.373(5) . ?
C6 N2 1.409(5) . ?
C7 C8 1.397(5) . ?
C7 C12 1.387(6) . ?
C7 N2 1.393(5) . ?
C8 C9 1.360(6) . ?
C8 O1 1.380(5) . ?
C9 H9 0.98(5) . ?
C9 C10 1.380(7) . ?
C10 H10 1.01(5) . ?
C10 C11 1.383(8) . ?
C11 H11 0.96(7) . ?
C11 C12 1.381(6) . ?
C12 H12 1.01(4) . ?
C13 C14 1.364(5) . ?
C13 C18 1.407(5) . ?
C13 N2 1.441(4) . ?
C14 H14 0.96(4) . ?
C14 C15 1.406(5) . ?
C15 H15 0.98(4) . ?
C15 C16 1.369(5) . ?
C16 C17 1.411(5) . ?
C16 C24 1.478(5) . ?
C17 C18 1.422(4) . ?
C17 C22 1.407(5) . ?
C18 C19 1.421(5) . ?
C19 H19 1.01(4) . ?
C19 C20 1.348(6) . ?
C20 H20 0.99(4) . ?
C20 C21 1.387(6) . ?
C21 H21 1.06(4) . ?
C21 C22 1.381(5) . ?
C22 C23 1.465(5) . ?
C23 N1 1.411(5) . ?
C23 O2 1.204(4) . ?
C24 N1 1.400(4) . ?
C24 O3 1.208(4) . ?
C25 H25 0.98(4) . ?
C25 C26 1.391(5) . ?
C25 C30 1.361(5) . ?
C26 H26 1.00(4) . ?
C26 C27 1.365(5) . ?
C27 C28 1.372(5) . ?
C27 N1 1.452(4) . ?
C28 H28 1.04(4) . ?
C28 C29 1.386(5) . ?
C29 H29 0.88(5) . ?
C29 C30 1.347(6) . ?
C30 F1 1.358(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 117(3) . . ?
C6 C1 H1 122(3) . . ?
C6 C1 C2 120.6(5) . . ?
C1 C2 H2 118(3) . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 123(3) . . ?
C2 C3 H3 122(3) . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 118(3) . . ?
C3 C4 H4 125(3) . . ?
C3 C4 C5 120.1(5) . . ?
C5 C4 H4 115(3) . . ?
C4 C5 C6 120.4(4) . . ?
O1 C5 C4 117.5(4) . . ?
O1 C5 C6 122.1(4) . . ?
C1 C6 C5 118.9(4) . . ?
C1 C6 N2 122.7(3) . . ?
C5 C6 N2 118.5(4) . . ?
C12 C7 C8 117.5(4) . . ?
C12 C7 N2 123.2(4) . . ?
N2 C7 C8 119.3(3) . . ?
C9 C8 C7 121.7(4) . . ?
C9 C8 O1 116.9(4) . . ?
O1 C8 C7 121.4(4) . . ?
C8 C9 H9 122(3) . . ?
C8 C9 C10 120.4(5) . . ?
C10 C9 H9 118(3) . . ?
C9 C10 H10 121(3) . . ?
C9 C10 C11 119.0(5) . . ?
C11 C10 H10 120(3) . . ?
C10 C11 H11 122(4) . . ?
C12 C11 C10 120.5(5) . . ?
C12 C11 H11 118(4) . . ?
C7 C12 H12 114(3) . . ?
C11 C12 C7 120.9(5) . . ?
C11 C12 H12 125(3) . . ?
C14 C13 C18 121.6(3) . . ?
C14 C13 N2 118.9(3) . . ?
C18 C13 N2 119.5(3) . . ?
C13 C14 H14 124(3) . . ?
C13 C14 C15 120.4(4) . . ?
C15 C14 H14 115(3) . . ?
C14 C15 H15 122(2) . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 118(2) . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 C24 119.1(3) . . ?
C17 C16 C24 120.4(3) . . ?
C16 C17 C18 119.8(3) . . ?
C22 C17 C16 120.6(3) . . ?
C22 C17 C18 119.6(3) . . ?
C13 C18 C17 117.7(3) . . ?
C13 C18 C19 124.3(3) . . ?
C19 C18 C17 118.0(3) . . ?
C18 C19 H19 117(2) . . ?
C20 C19 C18 121.1(4) . . ?
C20 C19 H19 122(2) . . ?
C19 C20 H20 119(3) . . ?
C19 C20 C21 120.9(4) . . ?
C21 C20 H20 120(3) . . ?
C20 C21 H21 124(2) . . ?
C22 C21 C20 120.6(4) . . ?
C22 C21 H21 115(2) . . ?
C17 C22 C23 120.9(3) . . ?
C21 C22 C17 119.8(3) . . ?
C21 C22 C23 119.4(3) . . ?
N1 C23 C22 116.2(3) . . ?
O2 C23 C22 124.0(3) . . ?
O2 C23 N1 119.9(3) . . ?
N1 C24 C16 116.1(3) . . ?
O3 C24 C16 123.4(3) . . ?
O3 C24 N1 120.4(3) . . ?
C26 C25 H25 119(2) . . ?
C30 C25 H25 123(2) . . ?
C30 C25 C26 117.8(4) . . ?
C25 C26 H26 118(2) . . ?
C27 C26 C25 119.9(4) . . ?
C27 C26 H26 122(2) . . ?
C26 C27 C28 120.7(3) . . ?
C26 C27 N1 119.7(3) . . ?
C28 C27 N1 119.6(3) . . ?
C27 C28 H28 120(2) . . ?
C27 C28 C29 119.7(4) . . ?
C29 C28 H28 120(2) . . ?
C28 C29 H29 120(3) . . ?
C30 C29 C28 118.4(4) . . ?
C30 C29 H29 121(3) . . ?
C29 C30 C25 123.5(3) . . ?
C29 C30 F1 118.2(3) . . ?
F1 C30 C25 118.2(4) . . ?
C23 N1 C27 117.3(3) . . ?
C24 N1 C23 125.6(3) . . ?
C24 N1 C27 117.1(3) . . ?
C6 N2 C13 120.0(3) . . ?
C7 N2 C6 119.5(3) . . ?
C7 N2 C13 119.7(3) . . ?
C5 O1 C8 118.3(3) . . ?

_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_2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2280422'
loop_
_audit_author_name
_audit_author_address
'Jieyu Tang'
;Dalian University of Technology
China
;
_audit_update_record             
;
2023-07-10 deposited with the CCDC.	2023-11-29 downloaded from the CCDC.
;
_audit_creation_date             2022-08-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        NI-PXZ-Ph
_chemical_formula_moiety         'C30 H18 N2 O3'
_chemical_formula_sum            'C30 H18 N2 O3'
_chemical_formula_weight         454.46
_chemical_absolute_configuration ?
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.7810(7)
_cell_length_b                   12.8680(6)
_cell_length_c                   13.2627(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2181.26(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5211
_cell_measurement_temperature    273.7
_cell_measurement_theta_max      23.081
_cell_measurement_theta_min      2.721
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.7165
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0656 after correction.
The Ratio of minimum to maximum transmission is 0.9616.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24469
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.724
_diffrn_reflns_theta_max         24.724
_diffrn_reflns_theta_min         2.205
_diffrn_ambient_temperature      273.7
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2789
_reflns_number_total             3716
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 983 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.070
_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)+(0.0437P)²+0.2953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1050
_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:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28),
  C29(H29), C30(H30)
;
_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
C1 C 0.6707(3) 1.1877(3) 0.3250(3) 0.0533(10) Uani 1 1 d . . . . .
H1 H 0.669704 1.258013 0.308890 0.064 Uiso 1 1 calc R U . . .
C2 C 0.6081(3) 1.1508(3) 0.3997(3) 0.0569(10) Uani 1 1 d . . . . .
H2 H 0.564182 1.195856 0.434456 0.068 Uiso 1 1 calc R U . . .
C3 C 0.6095(3) 1.0463(3) 0.4240(3) 0.0541(10) Uani 1 1 d . . . . .
H3 H 0.566331 1.020798 0.474730 0.065 Uiso 1 1 calc R U . . .
C4 C 0.6751(3) 0.9805(2) 0.3729(2) 0.0418(9) Uani 1 1 d . . . . .
C5 C 0.7374(3) 1.0168(3) 0.2971(3) 0.0523(10) Uani 1 1 d . . . . .
H5 H 0.780730 0.971608 0.261759 0.063 Uiso 1 1 calc R U . . .
C6 C 0.7356(3) 1.1212(3) 0.2733(3) 0.0557(10) Uani 1 1 d . . . . .
H6 H 0.778402 1.146641 0.222269 0.067 Uiso 1 1 calc R U . . .
C7 C 0.7537(3) 0.8416(2) 0.4724(3) 0.0442(9) Uani 1 1 d . . . . .
C8 C 0.6093(3) 0.8032(3) 0.3518(3) 0.0425(9) Uani 1 1 d . . . . .
C9 C 0.6141(3) 0.6930(2) 0.3814(3) 0.0399(8) Uani 1 1 d . . . . .
C10 C 0.7519(3) 0.7315(2) 0.5048(2) 0.0409(8) Uani 1 1 d . . . . .
C11 C 0.6816(3) 0.6613(2) 0.4598(2) 0.0381(8) Uani 1 1 d . . . . .
C12 C 0.8191(3) 0.6990(2) 0.5788(3) 0.0488(9) Uani 1 1 d . . . . .
H12 H 0.867120 0.745322 0.606194 0.059 Uiso 1 1 calc R U . . .
C13 C 0.8157(3) 0.5962(3) 0.6133(3) 0.0515(10) Uani 1 1 d . . . . .
H13 H 0.860788 0.574841 0.664217 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7464(3) 0.5273(2) 0.5725(3) 0.0442(9) Uani 1 1 d . . . . .
C15 C 0.6791(3) 0.5558(2) 0.4923(2) 0.0410(8) Uani 1 1 d . . . . .
C16 C 0.6111(3) 0.4861(2) 0.4427(3) 0.0484(9) Uani 1 1 d . . . . .
H16 H 0.608113 0.417210 0.463641 0.058 Uiso 1 1 calc R U . . .
C17 C 0.5501(3) 0.5179(3) 0.3652(3) 0.0542(10) Uani 1 1 d . . . . .
H17 H 0.507351 0.470345 0.332147 0.065 Uiso 1 1 calc R U . . .
C18 C 0.5509(3) 0.6218(3) 0.3347(3) 0.0511(10) Uani 1 1 d . . . . .
H18 H 0.507926 0.642939 0.281971 0.061 Uiso 1 1 calc R U . . .
C19 C 0.6002(4) 0.4718(3) 0.7274(3) 0.0636(11) Uani 1 1 d . . . . .
H19 H 0.603782 0.540611 0.706268 0.076 Uiso 1 1 calc R U . . .
C20 C 0.6664(3) 0.3988(3) 0.6854(3) 0.0501(9) Uani 1 1 d . . . . .
C21 C 0.6595(3) 0.2962(3) 0.7185(3) 0.0565(10) Uani 1 1 d . . . . .
C22 C 0.5887(4) 0.2684(4) 0.7914(3) 0.0704(13) Uani 1 1 d . . . . .
H22 H 0.584501 0.199657 0.812678 0.084 Uiso 1 1 calc R U . . .
C23 C 0.5239(4) 0.3420(4) 0.8332(3) 0.0816(15) Uani 1 1 d . . . . .
H23 H 0.476895 0.323275 0.883516 0.098 Uiso 1 1 calc R U . . .
C24 C 0.5286(4) 0.4434(4) 0.8007(3) 0.0771(14) Uani 1 1 d . . . . .
H24 H 0.483676 0.492874 0.827895 0.093 Uiso 1 1 calc R U . . .
C25 C 0.7934(3) 0.3423(3) 0.5612(3) 0.0456(9) Uani 1 1 d . . . . .
C26 C 0.7837(3) 0.2410(3) 0.5980(3) 0.0552(10) Uani 1 1 d . . . . .
C27 C 0.8344(4) 0.1604(3) 0.5519(4) 0.0670(13) Uani 1 1 d . . . . .
H27 H 0.827821 0.093386 0.577453 0.080 Uiso 1 1 calc R U . . .
C28 C 0.8947(4) 0.1778(3) 0.4685(4) 0.0712(13) Uani 1 1 d . . . . .
H28 H 0.929726 0.122799 0.437977 0.085 Uiso 1 1 calc R U . . .
C29 C 0.9038(4) 0.2764(3) 0.4297(3) 0.0688(12) Uani 1 1 d . . . . .
H29 H 0.943947 0.287971 0.372292 0.083 Uiso 1 1 calc R U . . .
C30 C 0.8529(3) 0.3583(3) 0.4762(3) 0.0565(11) Uani 1 1 d . . . . .
H30 H 0.858938 0.424986 0.449673 0.068 Uiso 1 1 calc R U . . .
N1 N 0.6789(2) 0.87146(19) 0.4006(2) 0.0421(7) Uani 1 1 d . . . . .
N2 N 0.7418(3) 0.4230(2) 0.6117(2) 0.0509(8) Uani 1 1 d . . . . .
O3 O 0.7247(3) 0.2196(2) 0.6826(2) 0.0763(9) Uani 1 1 d . . . . .
O001 O 0.5478(2) 0.83677(18) 0.29029(19) 0.0576(7) Uani 1 1 d . . . . .
O002 O 0.8151(2) 0.90471(18) 0.5053(2) 0.0710(9) 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
C1 H1 0.9300 . ?
C1 C2 1.359(5) . ?
C1 C6 1.374(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(5) . ?
C4 C5 1.365(5) . ?
C4 N1 1.451(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(5) . ?
C6 H6 0.9300 . ?
C7 C10 1.480(4) . ?
C7 N1 1.404(4) . ?
C7 O002 1.211(4) . ?
C8 C9 1.472(5) . ?
C8 N1 1.408(4) . ?
C8 O001 1.212(4) . ?
C9 C11 1.412(4) . ?
C9 C18 1.369(4) . ?
C10 C11 1.408(5) . ?
C10 C12 1.369(5) . ?
C11 C15 1.424(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.400(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(5) . ?
C14 C15 1.417(5) . ?
C14 N2 1.440(4) . ?
C15 C16 1.411(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.353(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.381(5) . ?
C19 C24 1.384(6) . ?
C20 C21 1.394(5) . ?
C20 N2 1.408(5) . ?
C21 C22 1.372(6) . ?
C21 O3 1.376(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.375(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.375(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.397(5) . ?
C25 C30 1.375(5) . ?
C25 N2 1.402(4) . ?
C26 C27 1.368(5) . ?
C26 O3 1.380(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.367(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.374(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.385(5) . ?
C30 H30 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
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.1(3) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.1(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 N1 119.5(3) . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 N1 119.9(3) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 120.1(4) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C10 116.7(3) . . ?
O002 C7 C10 123.2(3) . . ?
O002 C7 N1 120.1(3) . . ?
N1 C8 C9 116.8(3) . . ?
O001 C8 C9 123.3(3) . . ?
O001 C8 N1 119.8(3) . . ?
C11 C9 C8 120.0(3) . . ?
C18 C9 C8 119.9(3) . . ?
C18 C9 C11 120.0(3) . . ?
C11 C10 C7 120.1(3) . . ?
C12 C10 C7 119.4(3) . . ?
C12 C10 C11 120.5(3) . . ?
C9 C11 C15 119.0(3) . . ?
C10 C11 C9 121.1(3) . . ?
C10 C11 C15 119.9(3) . . ?
C10 C12 H12 119.9 . . ?
C10 C12 C13 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 N2 119.2(3) . . ?
C15 C14 N2 119.2(3) . . ?
C14 C15 C11 117.4(3) . . ?
C16 C15 C11 118.6(3) . . ?
C16 C15 C14 124.0(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.3(4) . . ?
C18 C17 H17 119.8 . . ?
C9 C18 C17 120.9(4) . . ?
C9 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 H19 119.7 . . ?
C20 C19 C24 120.6(4) . . ?
C24 C19 H19 119.7 . . ?
C19 C20 C21 118.6(4) . . ?
C19 C20 N2 123.3(3) . . ?
C21 C20 N2 118.1(3) . . ?
C22 C21 C20 120.7(4) . . ?
C22 C21 O3 117.2(4) . . ?
O3 C21 C20 122.1(4) . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.1(4) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.1(5) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 120.0 . . ?
C23 C24 C19 119.9(5) . . ?
C23 C24 H24 120.0 . . ?
C26 C25 N2 118.8(3) . . ?
C30 C25 C26 118.5(3) . . ?
C30 C25 N2 122.7(3) . . ?
C27 C26 C25 120.6(4) . . ?
C27 C26 O3 118.0(3) . . ?
O3 C26 C25 121.3(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.3(4) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.9 . . ?
C27 C28 C29 120.2(4) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 120.1 . . ?
C28 C29 C30 119.8(5) . . ?
C30 C29 H29 120.1 . . ?
C25 C30 C29 120.7(4) . . ?
C25 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C7 N1 C4 117.4(3) . . ?
C7 N1 C8 124.9(3) . . ?
C8 N1 C4 117.7(3) . . ?
C20 N2 C14 119.0(3) . . ?
C25 N2 C14 119.9(3) . . ?
C25 N2 C20 119.4(3) . . ?
C21 O3 C26 118.0(3) . . ?

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
C1 C2 C3 C4 0.5(6) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C2 C3 C4 N1 178.1(4) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C3 C4 N1 C7 -91.7(4) . . . . ?
C3 C4 N1 C8 89.8(4) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C5 C4 N1 C7 87.6(4) . . . . ?
C5 C4 N1 C8 -91.0(4) . . . . ?
C6 C1 C2 C3 0.1(6) . . . . ?
C7 C10 C11 C9 2.1(5) . . . . ?
C7 C10 C11 C15 -179.1(3) . . . . ?
C7 C10 C12 C13 177.4(3) . . . . ?
C8 C9 C11 C10 -5.9(5) . . . . ?
C8 C9 C11 C15 175.3(3) . . . . ?
C8 C9 C18 C17 -176.5(4) . . . . ?
C9 C8 N1 C4 -179.7(3) . . . . ?
C9 C8 N1 C7 1.9(5) . . . . ?
C9 C11 C15 C14 -178.8(3) . . . . ?
C9 C11 C15 C16 1.7(5) . . . . ?
C10 C7 N1 C4 176.1(3) . . . . ?
C10 C7 N1 C8 -5.5(5) . . . . ?
C10 C11 C15 C14 2.3(5) . . . . ?
C10 C11 C15 C16 -177.2(3) . . . . ?
C10 C12 C13 C14 0.9(6) . . . . ?
C11 C9 C18 C17 1.6(5) . . . . ?
C11 C10 C12 C13 -2.5(5) . . . . ?
C11 C15 C16 C17 0.7(5) . . . . ?
C12 C10 C11 C9 -178.0(3) . . . . ?
C12 C10 C11 C15 0.8(5) . . . . ?
C12 C13 C14 C15 2.3(6) . . . . ?
C12 C13 C14 N2 -177.8(3) . . . . ?
C13 C14 C15 C11 -3.9(5) . . . . ?
C13 C14 C15 C16 175.6(4) . . . . ?
C13 C14 N2 C20 95.7(4) . . . . ?
C13 C14 N2 C25 -99.4(4) . . . . ?
C14 C15 C16 C17 -178.7(3) . . . . ?
C15 C14 N2 C20 -84.4(4) . . . . ?
C15 C14 N2 C25 80.5(4) . . . . ?
C15 C16 C17 C18 -2.0(6) . . . . ?
C16 C17 C18 C9 0.9(6) . . . . ?
C18 C9 C11 C10 176.1(3) . . . . ?
C18 C9 C11 C15 -2.8(5) . . . . ?
C19 C20 C21 C22 -0.2(6) . . . . ?
C19 C20 C21 O3 -178.0(4) . . . . ?
C19 C20 N2 C14 -4.4(5) . . . . ?
C19 C20 N2 C25 -169.4(4) . . . . ?
C20 C19 C24 C23 0.9(7) . . . . ?
C20 C21 C22 C23 -0.4(6) . . . . ?
C20 C21 O3 C26 -12.9(5) . . . . ?
C21 C20 N2 C14 176.6(3) . . . . ?
C21 C20 N2 C25 11.6(5) . . . . ?
C21 C22 C23 C24 1.2(7) . . . . ?
C22 C21 O3 C26 169.2(3) . . . . ?
C22 C23 C24 C19 -1.4(7) . . . . ?
C24 C19 C20 C21 -0.1(6) . . . . ?
C24 C19 C20 N2 -179.1(4) . . . . ?
C25 C26 C27 C28 -0.6(6) . . . . ?
C25 C26 O3 C21 12.4(5) . . . . ?
C26 C25 C30 C29 -1.5(6) . . . . ?
C26 C25 N2 C14 -177.0(3) . . . . ?
C26 C25 N2 C20 -12.1(5) . . . . ?
C26 C27 C28 C29 -0.8(6) . . . . ?
C27 C26 O3 C21 -168.9(4) . . . . ?
C27 C28 C29 C30 1.0(7) . . . . ?
C28 C29 C30 C25 0.2(6) . . . . ?
C30 C25 C26 C27 1.7(6) . . . . ?
C30 C25 C26 O3 -179.6(3) . . . . ?
C30 C25 N2 C14 2.6(5) . . . . ?
C30 C25 N2 C20 167.5(3) . . . . ?
N1 C4 C5 C6 -178.0(3) . . . . ?
N1 C7 C10 C11 3.5(5) . . . . ?
N1 C7 C10 C12 -176.4(3) . . . . ?
N1 C8 C9 C11 4.0(5) . . . . ?
N1 C8 C9 C18 -178.0(3) . . . . ?
N2 C14 C15 C11 176.2(3) . . . . ?
N2 C14 C15 C16 -4.3(5) . . . . ?
N2 C20 C21 C22 178.9(3) . . . . ?
N2 C20 C21 O3 1.0(6) . . . . ?
N2 C25 C26 C27 -178.8(3) . . . . ?
N2 C25 C26 O3 -0.1(6) . . . . ?
N2 C25 C30 C29 179.0(4) . . . . ?
O3 C21 C22 C23 177.6(4) . . . . ?
O3 C26 C27 C28 -179.3(4) . . . . ?
O001 C8 C9 C11 -174.5(3) . . . . ?
O001 C8 C9 C18 3.6(5) . . . . ?
O001 C8 N1 C4 -1.2(5) . . . . ?
O001 C8 N1 C7 -179.6(3) . . . . ?
O002 C7 C10 C11 -177.0(4) . . . . ?
O002 C7 C10 C12 3.1(6) . . . . ?
O002 C7 N1 C4 -3.5(5) . . . . ?
O002 C7 N1 C8 174.9(3) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
