# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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 
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data_mo_20220422_ny_xwx_0m
_database_code_depnum_ccdc_archive 'CCDC 2238828'
loop_
_audit_author_name
_audit_author_address
'wenxin xiang'
;Nanjing University of Posts and Telecommunications
China
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-06-23 downloaded from the CCDC.
;
_audit_creation_date             2022-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 O, C10 H2 N4'
_chemical_formula_sum            'C26 H12 N4 O'
_chemical_formula_weight         396.40
_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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   7.9325(3)
_cell_length_b                   7.8534(4)
_cell_length_c                   15.8599(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.753(2)
_cell_angle_gamma                90
_cell_volume                     973.75(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3529
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      26.747
_cell_measurement_theta_min      2.594
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.3952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1151 before and 0.0649 after correction.
The Ratio of minimum to maximum transmission is 0.9180.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13819
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.594
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_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
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.849
_reflns_Friedel_fraction_max     0.815
_reflns_number_gt                3430
_reflns_number_total             4057
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 1266 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_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     256
_refine_ls_number_reflns         4057
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0740
_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)+(0.1087P)²+0.7897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2023
_refine_ls_wR_factor_ref         0.2152
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid bond restraints
 C9, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O1, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4), C3(H3), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C21(H21), C26(H26)
2.b Fitted hexagon refined as free rotating group:
 C2(C1,C6,C5,C4,C3), C8(C9,C10,C11,C12,C7)
;
_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
O1 O 0.6215(7) 0.4845(7) 0.5596(4) 0.0802(17) Uani 1 1 d . U . . .
C2 C 0.5360(5) 0.6563(7) 0.6822(3) 0.076(3) Uani 1 1 d G . . . .
H2 H 0.499305 0.559209 0.709965 0.092 Uiso 1 1 calc R U . . .
C1 C 0.6050(5) 0.6368(5) 0.6079(3) 0.0584(15) Uani 1 1 d G U . . .
C6 C 0.6587(5) 0.7787(5) 0.5673(2) 0.0374(12) Uani 1 1 d G . . . .
C5 C 0.6434(6) 0.9402(5) 0.6011(3) 0.0517(16) Uani 1 1 d G . . . .
H5 H 0.680122 1.037281 0.573332 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5744(6) 0.9597(7) 0.6754(3) 0.068(2) Uani 1 1 d G . . . .
H4 H 0.564018 1.070113 0.698509 0.081 Uiso 1 1 calc R U . . .
C3 C 0.5207(5) 0.8177(9) 0.7160(2) 0.091(4) Uani 1 1 d G . . . .
H3 H 0.473609 0.831079 0.766827 0.109 Uiso 1 1 calc R U . . .
C8 C 0.6883(5) 0.5487(4) 0.4899(3) 0.0531(16) Uani 1 1 d G . . . .
C9 C 0.7252(6) 0.4473(3) 0.4235(3) 0.080(2) Uani 1 1 d G U . . .
H9 H 0.702981 0.328422 0.423508 0.096 Uiso 1 1 calc R U . . .
C10 C 0.7945(6) 0.5198(5) 0.3571(3) 0.077(2) Uani 1 1 d G U . . .
H10 H 0.819642 0.450533 0.311715 0.092 Uiso 1 1 calc R U . . .
C11 C 0.8269(6) 0.6938(5) 0.3571(2) 0.0456(14) Uani 1 1 d G . . . .
C12 C 0.7901(5) 0.7952(3) 0.4234(3) 0.0340(10) Uani 1 1 d G . . . .
C7 C 0.7208(4) 0.7226(4) 0.4898(2) 0.0314(10) Uani 1 1 d G . . . .
C13 C 0.8343(7) 0.9739(6) 0.4169(3) 0.0365(11) Uani 1 1 d . . . . .
H13 H 0.811877 1.052462 0.459148 0.044 Uiso 1 1 calc R U . . .
C14 C 0.9087(8) 1.0290(9) 0.3495(5) 0.0578(18) Uani 1 1 d . . . . .
H14 H 0.938227 1.145691 0.345903 0.069 Uiso 1 1 calc R U . . .
C15 C 0.9412(9) 0.9158(12) 0.2865(4) 0.0604(19) Uani 1 1 d . . . . .
H15 H 0.991828 0.956074 0.240075 0.072 Uiso 1 1 calc R U . . .
C16 C 0.9025(8) 0.7550(12) 0.2908(4) 0.0576(17) Uani 1 1 d . . . . .
H16 H 0.926614 0.678991 0.247752 0.069 Uiso 1 1 calc R U . . .
N1 N 1.0537(9) 0.6511(7) 0.7221(4) 0.0573(15) Uani 1 1 d . . . . .
N2 N 1.0770(8) 0.2300(6) 0.5811(4) 0.0529(13) Uani 1 1 d . . . . .
N3 N 1.3836(8) 0.7053(7) 0.2765(4) 0.0532(13) Uani 1 1 d . . . . .
N4 N 1.3568(7) 1.1225(6) 0.4152(4) 0.0492(12) Uani 1 1 d . . . . .
C17 C 1.0938(8) 0.6584(7) 0.6558(4) 0.0402(12) Uani 1 1 d . . . . .
C18 C 1.1510(6) 0.6701(6) 0.5739(3) 0.0321(11) Uani 1 1 d . . . . .
C19 C 1.1634(6) 0.5206(6) 0.5264(3) 0.0309(10) Uani 1 1 d . . . . .
C20 C 1.1149(7) 0.3588(7) 0.5565(3) 0.0382(11) Uani 1 1 d . . . . .
C21 C 1.2249(7) 0.5303(6) 0.4485(3) 0.0355(11) Uani 1 1 d . . . . .
H21 H 1.233983 0.430126 0.415926 0.043 Uiso 1 1 calc R U . . .
C22 C 1.2720(6) 0.6855(6) 0.4196(4) 0.0334(11) Uani 1 1 d . . . . .
C23 C 1.3356(7) 0.6957(7) 0.3397(4) 0.0376(12) Uani 1 1 d . . . . .
C24 C 1.2569(6) 0.8346(6) 0.4686(3) 0.0307(11) Uani 1 1 d . . . . .
C25 C 1.3128(7) 0.9965(7) 0.4393(3) 0.0340(10) Uani 1 1 d . . . . .
C26 C 1.1951(6) 0.8247(6) 0.5446(4) 0.0321(11) Uani 1 1 d . . . . .
H26 H 1.183189 0.925095 0.576499 0.038 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
O1 C1 1.437(8) . ?
O1 C8 1.400(7) . ?
C2 H2 0.9500 . ?
C2 C1 1.3900 . ?
C2 C3 1.3900 . ?
C1 C6 1.3900 . ?
C6 C5 1.3900 . ?
C6 C7 1.467(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C3 H3 0.9500 . ?
C8 C9 1.3900 . ?
C8 C7 1.3900 . ?
C9 H9 0.9500 . ?
C9 C10 1.3900 . ?
C10 H10 0.9500 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C11 C16 1.382(8) . ?
C12 C7 1.3900 . ?
C12 C13 1.455(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.304(12) . ?
C16 H16 0.9500 . ?
N1 C17 1.150(8) . ?
N2 C20 1.142(7) . ?
N3 C23 1.133(8) . ?
N4 C25 1.137(7) . ?
C17 C18 1.450(7) . ?
C18 C19 1.407(7) . ?
C18 C26 1.367(7) . ?
C19 C20 1.433(7) . ?
C19 C21 1.406(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.376(7) . ?
C22 C23 1.443(8) . ?
C22 C24 1.422(7) . ?
C24 C25 1.449(7) . ?
C24 C26 1.378(7) . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C1 101.7(4) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C1 O1 128.9(4) . . ?
C2 C1 C6 120.0 . . ?
C6 C1 O1 111.0(4) . . ?
C1 C6 C7 108.6(3) . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 131.3(3) . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C9 C8 O1 123.3(4) . . ?
C9 C8 C7 120.0 . . ?
C7 C8 O1 116.7(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C16 C11 C10 116.5(4) . . ?
C16 C11 C12 123.4(4) . . ?
C11 C12 C13 114.5(3) . . ?
C7 C12 C11 120.0 . . ?
C7 C12 C13 125.5(3) . . ?
C8 C7 C6 101.9(3) . . ?
C12 C7 C6 138.0(3) . . ?
C12 C7 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(5) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(7) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(7) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.9(7) . . ?
C15 C16 H16 119.6 . . ?
N1 C17 C18 177.7(7) . . ?
C19 C18 C17 119.2(4) . . ?
C26 C18 C17 119.8(5) . . ?
C26 C18 C19 121.0(5) . . ?
C18 C19 C20 121.0(5) . . ?
C21 C19 C18 119.4(4) . . ?
C21 C19 C20 119.6(4) . . ?
N2 C20 C19 179.5(7) . . ?
C19 C21 H21 120.2 . . ?
C22 C21 C19 119.7(5) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 119.8(5) . . ?
C21 C22 C24 119.7(5) . . ?
C24 C22 C23 120.6(5) . . ?
N3 C23 C22 179.0(6) . . ?
C22 C24 C25 119.3(5) . . ?
C26 C24 C22 120.5(5) . . ?
C26 C24 C25 120.2(5) . . ?
N4 C25 C24 178.9(6) . . ?
C18 C26 C24 119.8(5) . . ?
C18 C26 H26 120.1 . . ?
C24 C26 H26 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C6 C5 176.2(4) . . . . ?
O1 C1 C6 C7 -2.2(4) . . . . ?
O1 C8 C9 C10 -178.8(4) . . . . ?
O1 C8 C7 C6 -3.2(4) . . . . ?
O1 C8 C7 C12 178.9(4) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 C7 -178.4(3) . . . . ?
C1 O1 C8 C9 -179.3(3) . . . . ?
C1 O1 C8 C7 1.9(5) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C1 C6 C7 C8 3.1(3) . . . . ?
C1 C6 C7 C12 -179.5(3) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C6 C7 C8 -175.0(3) . . . . ?
C5 C6 C7 C12 2.4(6) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C3 C2 C1 O1 -175.4(5) . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C8 O1 C1 C2 176.0(3) . . . . ?
C8 O1 C1 C6 0.3(4) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C8 C7 C6 178.0(3) . . . . ?
C9 C8 C7 C12 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C9 C10 C11 C16 177.4(4) . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C10 C11 C12 C13 178.4(4) . . . . ?
C10 C11 C16 C15 -178.5(5) . . . . ?
C11 C12 C7 C6 -177.1(4) . . . . ?
C11 C12 C7 C8 0.0 . . . . ?
C11 C12 C13 C14 -0.9(6) . . . . ?
C12 C11 C16 C15 -1.2(8) . . . . ?
C12 C13 C14 C15 0.6(8) . . . . ?
C7 C6 C5 C4 177.9(4) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C7 C12 C13 C14 177.4(4) . . . . ?
C13 C12 C7 C6 4.7(6) . . . . ?
C13 C12 C7 C8 -178.2(5) . . . . ?
C13 C14 C15 C16 -0.5(9) . . . . ?
C14 C15 C16 C11 0.8(10) . . . . ?
C16 C11 C12 C7 -177.2(5) . . . . ?
C16 C11 C12 C13 1.3(5) . . . . ?
C17 C18 C19 C20 2.1(7) . . . . ?
C17 C18 C19 C21 -177.6(5) . . . . ?
C17 C18 C26 C24 177.1(5) . . . . ?
C18 C19 C21 C22 -0.1(7) . . . . ?
C19 C18 C26 C24 -1.7(7) . . . . ?
C19 C21 C22 C23 179.8(5) . . . . ?
C19 C21 C22 C24 -0.4(7) . . . . ?
C20 C19 C21 C22 -179.8(5) . . . . ?
C21 C22 C24 C25 177.7(5) . . . . ?
C21 C22 C24 C26 -0.2(7) . . . . ?
C22 C24 C26 C18 1.2(6) . . . . ?
C23 C22 C24 C25 -2.5(7) . . . . ?
C23 C22 C24 C26 179.6(5) . . . . ?
C25 C24 C26 C18 -176.6(5) . . . . ?
C26 C18 C19 C20 -179.1(5) . . . . ?
C26 C18 C19 C21 1.2(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_cu_20220408_ny_xwx_0m
_database_code_depnum_ccdc_archive 'CCDC 2238829'
loop_
_audit_author_name
_audit_author_address
'wenxin xiang'
;Nanjing University of Posts and Telecommunications
China
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-06-23 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C16 H10 O), C10 H2 N4'
_chemical_formula_sum            'C26 H12 N4 O'
_chemical_formula_weight         396.40
_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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.9376(8)
_cell_length_b                   7.9412(8)
_cell_length_c                   15.8417(18)
_cell_angle_alpha                93.490(9)
_cell_angle_beta                 100.212(8)
_cell_angle_gamma                92.313(8)
_cell_volume                     979.59(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3654
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      69.610
_cell_measurement_theta_min      2.841
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1380 before and 0.0855 after correction.
The Ratio of minimum to maximum transmission is 0.6355.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8802
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.916
_diffrn_reflns_theta_min         2.841
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2350
_reflns_number_total             3599
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.1449
_refine_ls_R_factor_gt           0.1050
_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)+(0.1704P)²+0.4305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2910
_refine_ls_wR_factor_ref         0.3339
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C16-C19 \\sim C16A-C19A
 with sigma of 0.04
 C18-C20 \\sim C18A-C20A
 with sigma of 0.04
 C15-C18 \\sim C15A-C18A
 with sigma of 0.04
 C17-C21 \\sim C17A-C21A
 with sigma of 0.04
 C11-C12 \\sim C11A-C12A
 with sigma of 0.02
 C11-C16 \\sim C11A-C16A
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 C13-C14 \\sim C13A-C14A
 with sigma of 0.02
 C22-C24 \\sim C22A-C24A
 with sigma of 0.04
 C24-C26 \\sim C24A-C26A
 with sigma of 0.04
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.04
 C15-C20 \\sim C15A-C20A
 with sigma of 0.04
 C17-C22 \\sim C17A-C22A
 with sigma of 0.02
 C16-C22 \\sim C16A-C22A
 with sigma of 0.04
 C17-C18 \\sim C17A-C18A
 with sigma of 0.04
 C18-C19 \\sim C18A-C19A
 with sigma of 0.04
 C18-C21 \\sim C18A-C21A
 with sigma of 0.04
 C21-C25 \\sim C21A-C25A
 with sigma of 0.04
 C21-C22 \\sim C21A-C22A
 with sigma of 0.02
 C21-C26 \\sim C21A-C26A
 with sigma of 0.02
 C22-C23 \\sim C22A-C23A
 with sigma of 0.02
 C15-C17 \\sim C15A-C17A
 with sigma of 0.04
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
 C15-C19 \\sim C15A-C19A
 with sigma of 0.04
 C24-C25 \\sim C24A-C25A
 with sigma of 0.02
 C16-C18 \\sim C16A-C18A
 with sigma of 0.04
 C25-C26 \\sim C25A-C26A
 with sigma of 0.02
 C16-C20 \\sim C16A-C20A
 with sigma of 0.04
 C17-C19 \\sim C17A-C19A
 with sigma of 0.04
 C17-C23 \\sim C17A-C23A
 with sigma of 0.04
 O1-C17 \\sim O1A-C17A
 with sigma of 0.04
 O1-C18 \\sim O1A-C18A
 with sigma of 0.04
 O1-C19 \\sim O1A-C19A
 with sigma of 0.04
 O1-C21 \\sim O1A-C21A
 with sigma of 0.04
 C18-C22 \\sim C18A-C22A
 with sigma of 0.04
 O1-C22 \\sim O1A-C22A
 with sigma of 0.04
 O1-C26 \\sim O1A-C26A
 with sigma of 0.04
 C19-C20 \\sim C19A-C20A
 with sigma of 0.04
 C11-C13 \\sim C11A-C13A
 with sigma of 0.04
 C11-C15 \\sim C11A-C15A
 with sigma of 0.04
 C11-C17 \\sim C11A-C17A
 with sigma of 0.04
 C21-C23 \\sim C21A-C23A
 with sigma of 0.04
 C12-C14 \\sim C12A-C14A
 with sigma of 0.04
 C12-C16 \\sim C12A-C16A
 with sigma of 0.04
 C22-C26 \\sim C22A-C26A
 with sigma of 0.04
 C13-C15 \\sim C13A-C15A
 with sigma of 0.04
 C23-C25 \\sim C23A-C25A
 with sigma of 0.04
 C14-C15 \\sim C14A-C15A
 with sigma of 0.04
 C14-C16 \\sim C14A-C16A
 with sigma of 0.04
 C14-C19 \\sim C14A-C19A
 with sigma of 0.04
 C14-C20 \\sim C14A-C20A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C21, C22, C23, C24, C25, C26
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O1A)=Sof(C26A)=Sof(H26A)=Sof(C25A)=Sof(H25A)=Sof(C24A)=Sof(H24A)=
 Sof(C23A)=Sof(H23A)=Sof(C22A)=Sof(C21A)=Sof(C15A)=Sof(C16A)=Sof(C11A)=
 Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=
 Sof(C17A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=1-FVAR(1)
 Sof(O1)=Sof(C14)=Sof(H14)=Sof(C13)=Sof(H13)=Sof(C12)=Sof(H12)=Sof(C11)=
 Sof(H11)=Sof(C20)=Sof(H20)=Sof(C15)=Sof(C16)=Sof(C17)=Sof(C18)=Sof(C19)=
 Sof(H19)=Sof(C21)=Sof(C22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=
 Sof(H25)=Sof(C26)=Sof(H26)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C12(H12), C11(H11), C20(H20), C19(H19), C23(H23),
 C24(H24), C25(H25), C26(H26), C5(H5), C10(H10), C26A(H26A), C25A(H25A),
 C24A(H24A), C23A(H23A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A),
 C19A(H19A), C20A(H20A)
5.b Fitted hexagon refined as free rotating group:
 C20(C15,C16,C17,C18,C19), C26A(C25A,C24A,C23A,C22A,C21A), C15A(C16A,C11A,C12A,
 C13A,C14A)
;
_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
O1 O 0.6059(16) 0.4955(15) 0.1808(9) 0.091(3) Uani 0.457(12) 1 d D . P A 1
C14 C 0.331(3) 0.281(3) 0.4581(13) 0.115(9) Uani 0.457(12) 1 d D . P A 1
H14 H 0.304472 0.362774 0.499184 0.138 Uiso 0.457(12) 1 calc R U P A 1
C13 C 0.306(4) 0.112(3) 0.4667(19) 0.142(15) Uani 0.457(12) 1 d D . P A 1
H13 H 0.264934 0.074871 0.515568 0.170 Uiso 0.457(12) 1 calc R U P A 1
C12 C 0.340(2) -0.005(3) 0.4036(16) 0.118(17) Uani 0.457(12) 1 d D . P A 1
H12 H 0.310478 -0.121027 0.407492 0.142 Uiso 0.457(12) 1 calc R U P A 1
C11 C 0.414(2) 0.042(2) 0.3357(13) 0.073(7) Uani 0.457(12) 1 d D . P A 1
H11 H 0.446839 -0.041109 0.297013 0.088 Uiso 0.457(12) 1 calc R U P A 1
C20 C 0.4318(15) 0.5008(14) 0.3822(7) 0.098(5) Uani 0.457(12) 1 d DG . P A 1
H20 H 0.402981 0.578522 0.424713 0.117 Uiso 0.457(12) 1 calc R U P A 1
C15 C 0.3992(19) 0.3285(16) 0.3863(8) 0.065(5) Uani 0.457(12) 1 d DG . P A 1
C16 C 0.4413(19) 0.2147(11) 0.3241(9) 0.046(3) Uani 0.457(12) 1 d DG . P A 1
C17 C 0.5159(17) 0.2733(12) 0.2577(8) 0.052(4) Uani 0.457(12) 1 d DG . P A 1
C18 C 0.5485(14) 0.4456(12) 0.2536(8) 0.068(4) Uani 0.457(12) 1 d DG . P A 1
C19 C 0.5064(12) 0.5594(10) 0.3158(8) 0.102(6) Uani 0.457(12) 1 d DG . P A 1
H19 H 0.528703 0.677131 0.312954 0.123 Uiso 0.457(12) 1 calc R U P A 1
C21 C 0.616(3) 0.337(2) 0.1351(16) 0.085(5) Uani 0.457(12) 1 d D . P A 1
C22 C 0.577(3) 0.197(2) 0.1783(13) 0.057(4) Uani 0.457(12) 1 d D . P A 1
C23 C 0.594(2) 0.031(2) 0.1455(13) 0.069(5) Uani 0.457(12) 1 d D . P A 1
H23 H 0.558705 -0.063869 0.172654 0.083 Uiso 0.457(12) 1 calc R U P A 1
C24 C 0.665(4) 0.014(3) 0.0711(15) 0.110(6) Uani 0.457(12) 1 d D . P A 1
H24 H 0.688725 -0.095874 0.050099 0.131 Uiso 0.457(12) 1 calc R U P A 1
C25 C 0.701(3) 0.153(3) 0.0272(16) 0.127(7) Uani 0.457(12) 1 d D . P A 1
H25 H 0.741771 0.135824 -0.025307 0.153 Uiso 0.457(12) 1 calc R U P A 1
C26 C 0.679(2) 0.315(3) 0.0574(15) 0.116(7) Uani 0.457(12) 1 d D . P A 1
H26 H 0.704963 0.409655 0.027022 0.139 Uiso 0.457(12) 1 calc R U P A 1
N1 N 0.8388(6) 0.3200(5) 0.4836(3) 0.0854(12) Uani 1 1 d . . . . .
N2 N 0.8740(5) -0.1158(5) 0.3452(3) 0.0832(11) Uani 1 1 d . . . . .
N3 N 1.1880(6) 0.3308(5) 0.0434(3) 0.0883(12) Uani 1 1 d . . . . .
N4 N 1.1233(6) 0.7653(5) 0.1716(3) 0.0912(13) Uani 1 1 d . . . . .
C1 C 0.8855(6) 0.3217(5) 0.4188(3) 0.0706(11) Uani 1 1 d . . . . .
C2 C 0.9469(5) 0.3248(5) 0.3390(3) 0.0639(10) Uani 1 1 d . . . . .
C3 C 0.9670(5) 0.1708(5) 0.2931(3) 0.0645(10) Uani 1 1 d . . . . .
C4 C 0.9180(6) 0.0130(5) 0.3238(3) 0.0698(11) Uani 1 1 d . . . . .
C5 C 1.0347(5) 0.1740(5) 0.2182(3) 0.0630(10) Uani 1 1 d . . . . .
H5 H 1.054174 0.071086 0.188448 0.076 Uiso 1 1 calc R U . . .
C6 C 1.0734(5) 0.3249(5) 0.1870(3) 0.0626(10) Uani 1 1 d . . . . .
C7 C 1.1376(6) 0.3289(5) 0.1076(3) 0.0716(11) Uani 1 1 d . . . . .
C8 C 1.0505(5) 0.4800(5) 0.2318(3) 0.0649(10) Uani 1 1 d . . . . .
C9 C 1.0901(6) 0.6378(5) 0.1984(3) 0.0758(12) Uani 1 1 d . . . . .
C10 C 0.9875(5) 0.4781(5) 0.3074(3) 0.0677(10) Uani 1 1 d . . . . .
H10 H 0.971687 0.581315 0.337849 0.081 Uiso 1 1 calc R U . . .
O1A O 0.4462(10) 0.4891(11) 0.3346(7) 0.101(4) Uani 0.543(12) 1 d D . P A 2
C26A C 0.343(2) 0.2909(19) 0.4336(11) 0.131(10) Uani 0.543(12) 1 d DG . P A 2
H26A H 0.319816 0.383275 0.470059 0.157 Uiso 0.543(12) 1 calc R U P A 2
C25A C 0.306(2) 0.126(2) 0.4524(9) 0.122(11) Uani 0.543(12) 1 d DG . P A 2
H25A H 0.257166 0.106174 0.501720 0.146 Uiso 0.543(12) 1 calc R U P A 2
C24A C 0.3399(19) -0.0088(16) 0.3991(11) 0.107(11) Uani 0.543(12) 1 d DG . P A
2
H24A H 0.314483 -0.121273 0.411932 0.129 Uiso 0.543(12) 1 calc R U P A 2
C23A C 0.4112(17) 0.0207(14) 0.3269(9) 0.073(6) Uani 0.543(12) 1 d DG . P A 2
H23A H 0.434450 -0.071622 0.290483 0.087 Uiso 0.543(12) 1 calc R U P A 2
C22A C 0.4484(18) 0.1853(16) 0.3081(9) 0.070(4) Uani 0.543(12) 1 d DG . P A 2
C21A C 0.4144(19) 0.3204(14) 0.3615(11) 0.075(4) Uani 0.543(12) 1 d DG . P A 2
C15A C 0.644(2) 0.3398(15) 0.1166(12) 0.084(5) Uani 0.543(12) 1 d DG . P A 2
C16A C 0.587(3) 0.2201(19) 0.1671(10) 0.079(6) Uani 0.543(12) 1 d DG . P A 2
C11A C 0.609(2) 0.0497(17) 0.1491(12) 0.092(7) Uani 0.543(12) 1 d DG . P A 2
H11A H 0.570050 -0.032197 0.183570 0.111 Uiso 0.543(12) 1 calc R U P A 2
C12A C 0.687(3) -0.0010(16) 0.0806(13) 0.105(7) Uani 0.543(12) 1 d DG . P A 2
H12A H 0.702136 -0.117521 0.068347 0.127 Uiso 0.543(12) 1 calc R U P A 2
C13A C 0.744(2) 0.119(2) 0.0302(10) 0.106(5) Uani 0.543(12) 1 d DG . P A 2
H13A H 0.797649 0.084080 -0.016615 0.127 Uiso 0.543(12) 1 calc R U P A 2
C14A C 0.722(2) 0.289(2) 0.0481(10) 0.099(5) Uani 0.543(12) 1 d DG . P A 2
H14A H 0.761077 0.371006 0.013647 0.119 Uiso 0.543(12) 1 calc R U P A 2
C17A C 0.5155(19) 0.2740(13) 0.2375(10) 0.060(3) Uani 0.543(12) 1 d D . P A 2
C18A C 0.4979(15) 0.4464(14) 0.2572(9) 0.071(3) Uani 0.543(12) 1 d D . P A 2
C19A C 0.5596(17) 0.5677(13) 0.2073(10) 0.110(5) Uani 0.543(12) 1 d D . P A 2
H19A H 0.561914 0.685495 0.222359 0.133 Uiso 0.543(12) 1 calc R U P A 2
C20A C 0.617(2) 0.503(2) 0.1340(12) 0.100(4) Uani 0.543(12) 1 d D . P A 2
H20A H 0.638970 0.580222 0.093419 0.120 Uiso 0.543(12) 1 calc R 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
O1 C18 1.385(15) . ?
O1 C21 1.43(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.363(18) . ?
C14 C15 1.407(19) . ?
C13 H13 0.9500 . ?
C13 C12 1.391(17) . ?
C12 H12 0.9500 . ?
C12 C11 1.381(14) . ?
C11 H11 0.9500 . ?
C11 C16 1.405(13) . ?
C20 H20 0.9500 . ?
C20 C15 1.3900 . ?
C20 C19 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C17 C22 1.528(13) . ?
C18 C19 1.3900 . ?
C19 H19 0.9500 . ?
C21 C22 1.391(15) . ?
C21 C26 1.413(15) . ?
C22 C23 1.403(13) . ?
C23 H23 0.9500 . ?
C23 C24 1.395(13) . ?
C24 H24 0.9500 . ?
C24 C25 1.390(17) . ?
C25 H25 0.9500 . ?
C25 C26 1.376(17) . ?
C26 H26 0.9500 . ?
N1 C1 1.152(6) . ?
N2 C4 1.157(5) . ?
N3 C7 1.158(6) . ?
N4 C9 1.159(6) . ?
C1 C2 1.434(6) . ?
C2 C3 1.414(6) . ?
C2 C10 1.392(6) . ?
C3 C4 1.436(6) . ?
C3 C5 1.388(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.368(5) . ?
C6 C7 1.439(6) . ?
C6 C8 1.419(6) . ?
C8 C9 1.434(6) . ?
C8 C10 1.377(6) . ?
C10 H10 0.9500 . ?
O1A C21A 1.456(15) . ?
O1A C18A 1.388(17) . ?
C26A H26A 0.9500 . ?
C26A C25A 1.3900 . ?
C26A C21A 1.3900 . ?
C25A H25A 0.9500 . ?
C25A C24A 1.3900 . ?
C24A H24A 0.9500 . ?
C24A C23A 1.3900 . ?
C23A H23A 0.9500 . ?
C23A C22A 1.3900 . ?
C22A C21A 1.3900 . ?
C22A C17A 1.519(13) . ?
C15A C16A 1.3900 . ?
C15A C14A 1.3900 . ?
C15A C20A 1.339(17) . ?
C16A C11A 1.3900 . ?
C16A C17A 1.393(13) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.3900 . ?
C12A H12A 0.9500 . ?
C12A C13A 1.3900 . ?
C13A H13A 0.9500 . ?
C13A C14A 1.3900 . ?
C14A H14A 0.9500 . ?
C17A C18A 1.403(13) . ?
C18A C19A 1.408(16) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.399(19) . ?
C20A H20A 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
C18 O1 C21 101.5(11) . . ?
C13 C14 H14 121.2 . . ?
C13 C14 C15 117.6(17) . . ?
C15 C14 H14 121.2 . . ?
C14 C13 H13 120.1 . . ?
C14 C13 C12 119.9(19) . . ?
C12 C13 H13 120.1 . . ?
C13 C12 H12 119.0 . . ?
C11 C12 C13 122.1(15) . . ?
C11 C12 H12 119.0 . . ?
C12 C11 H11 120.2 . . ?
C12 C11 C16 119.5(13) . . ?
C16 C11 H11 120.2 . . ?
C15 C20 H20 120.0 . . ?
C15 C20 C19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C15 C14 115.9(11) . . ?
C16 C15 C14 124.0(11) . . ?
C16 C15 C20 120.0 . . ?
C15 C16 C11 116.6(10) . . ?
C15 C16 C17 120.0 . . ?
C17 C16 C11 123.3(10) . . ?
C16 C17 C22 137.0(9) . . ?
C18 C17 C16 120.0 . . ?
C18 C17 C22 103.0(9) . . ?
O1 C18 C17 116.6(8) . . ?
O1 C18 C19 123.0(8) . . ?
C17 C18 C19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C22 C21 O1 114.5(14) . . ?
C22 C21 C26 120.3(14) . . ?
C26 C21 O1 124.8(16) . . ?
C21 C22 C17 103.8(11) . . ?
C21 C22 C23 121.8(11) . . ?
C23 C22 C17 134.4(14) . . ?
C22 C23 H23 121.5 . . ?
C24 C23 C22 116.9(12) . . ?
C24 C23 H23 121.5 . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 121.1(15) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 119.0 . . ?
C26 C25 C24 122.1(16) . . ?
C26 C25 H25 119.0 . . ?
C21 C26 H26 121.2 . . ?
C25 C26 C21 117.6(15) . . ?
C25 C26 H26 121.2 . . ?
N1 C1 C2 178.9(5) . . ?
C3 C2 C1 119.5(3) . . ?
C10 C2 C1 120.3(4) . . ?
C10 C2 C3 120.2(4) . . ?
C2 C3 C4 120.2(4) . . ?
C5 C3 C2 119.3(4) . . ?
C5 C3 C4 120.5(4) . . ?
N2 C4 C3 177.0(5) . . ?
C3 C5 H5 119.9 . . ?
C6 C5 C3 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 120.4(4) . . ?
C5 C6 C8 120.8(4) . . ?
C8 C6 C7 118.8(4) . . ?
N3 C7 C6 179.3(5) . . ?
C6 C8 C9 120.4(4) . . ?
C10 C8 C6 119.4(4) . . ?
C10 C8 C9 120.1(4) . . ?
N4 C9 C8 179.5(6) . . ?
C2 C10 H10 120.0 . . ?
C8 C10 C2 120.0(4) . . ?
C8 C10 H10 120.0 . . ?
C18A O1A C21A 99.4(9) . . ?
C25A C26A H26A 120.0 . . ?
C25A C26A C21A 120.0 . . ?
C21A C26A H26A 120.0 . . ?
C26A C25A H25A 120.0 . . ?
C26A C25A C24A 120.0 . . ?
C24A C25A H25A 120.0 . . ?
C25A C24A H24A 120.0 . . ?
C23A C24A C25A 120.0 . . ?
C23A C24A H24A 120.0 . . ?
C24A C23A H23A 120.0 . . ?
C22A C23A C24A 120.0 . . ?
C22A C23A H23A 120.0 . . ?
C23A C22A C21A 120.0 . . ?
C23A C22A C17A 137.8(9) . . ?
C21A C22A C17A 102.2(9) . . ?
C26A C21A O1A 123.0(11) . . ?
C22A C21A O1A 116.8(11) . . ?
C22A C21A C26A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C20A C15A C16A 118.7(11) . . ?
C20A C15A C14A 121.3(11) . . ?
C15A C16A C11A 120.0 . . ?
C15A C16A C17A 119.1(10) . . ?
C11A C16A C17A 120.9(10) . . ?
C16A C11A H11A 120.0 . . ?
C12A C11A C16A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C11A C12A C13A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A C12A 120.0 . . ?
C14A C13A H13A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C13A C14A C15A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C16A C17A C22A 134.4(10) . . ?
C16A C17A C18A 120.9(11) . . ?
C18A C17A C22A 104.6(10) . . ?
O1A C18A C17A 116.6(9) . . ?
O1A C18A C19A 122.6(11) . . ?
C17A C18A C19A 119.8(11) . . ?
C18A C19A H19A 122.3 . . ?
C20A C19A C18A 115.4(11) . . ?
C20A C19A H19A 122.3 . . ?
C15A C20A C19A 125.2(13) . . ?
C15A C20A H20A 117.4 . . ?
C19A C20A H20A 117.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C18 C19 C20 172.8(13) . . . . ?
O1 C21 C22 C17 7(2) . . . . ?
O1 C21 C22 C23 -175(2) . . . . ?
O1 C21 C26 C25 172(2) . . . . ?
C14 C13 C12 C11 6(3) . . . . ?
C14 C15 C16 C11 -0.4(14) . . . . ?
C14 C15 C16 C17 -176.6(14) . . . . ?
C13 C14 C15 C20 -176.8(16) . . . . ?
C13 C14 C15 C16 0(2) . . . . ?
C13 C12 C11 C16 -7(2) . . . . ?
C12 C11 C16 C15 3.7(14) . . . . ?
C12 C11 C16 C17 179.7(11) . . . . ?
C11 C16 C17 C18 -175.9(13) . . . . ?
C11 C16 C17 C22 5(2) . . . . ?
C20 C15 C16 C11 176.2(12) . . . . ?
C20 C15 C16 C17 0.0 . . . . ?
C15 C14 C13 C12 -3(3) . . . . ?
C15 C20 C19 C18 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C15 C16 C17 C22 -179(2) . . . . ?
C16 C17 C18 O1 -173.3(12) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C16 C17 C22 C21 171.8(14) . . . . ?
C16 C17 C22 C23 -6(4) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C17 C22 C23 C24 -177(3) . . . . ?
C18 O1 C21 C22 -3(2) . . . . ?
C18 O1 C21 C26 -176(2) . . . . ?
C18 C17 C22 C21 -7.0(16) . . . . ?
C18 C17 C22 C23 175(2) . . . . ?
C19 C20 C15 C14 176.9(13) . . . . ?
C19 C20 C15 C16 0.0 . . . . ?
C21 O1 C18 C17 -1.9(16) . . . . ?
C21 O1 C18 C19 -175.0(14) . . . . ?
C21 C22 C23 C24 5(2) . . . . ?
C22 C17 C18 O1 5.8(14) . . . . ?
C22 C17 C18 C19 179.0(14) . . . . ?
C22 C21 C26 C25 0(3) . . . . ?
C22 C23 C24 C25 -6(3) . . . . ?
C23 C24 C25 C26 4(3) . . . . ?
C24 C25 C26 C21 -1(3) . . . . ?
C26 C21 C22 C17 180(2) . . . . ?
C26 C21 C22 C23 -2(2) . . . . ?
C1 C2 C3 C4 3.2(6) . . . . ?
C1 C2 C3 C5 -176.7(4) . . . . ?
C1 C2 C10 C8 178.3(4) . . . . ?
C2 C3 C5 C6 -3.2(6) . . . . ?
C3 C2 C10 C8 -1.2(6) . . . . ?
C3 C5 C6 C7 -177.7(4) . . . . ?
C3 C5 C6 C8 2.0(6) . . . . ?
C4 C3 C5 C6 176.8(4) . . . . ?
C5 C6 C8 C9 -179.5(4) . . . . ?
C5 C6 C8 C10 -0.4(6) . . . . ?
C6 C8 C10 C2 0.0(6) . . . . ?
C7 C6 C8 C9 0.2(6) . . . . ?
C7 C6 C8 C10 179.3(4) . . . . ?
C9 C8 C10 C2 179.1(4) . . . . ?
C10 C2 C3 C4 -177.2(4) . . . . ?
C10 C2 C3 C5 2.8(6) . . . . ?
O1A C18A C19A C20A 175.9(13) . . . . ?
C26A C25A C24A C23A 0.0 . . . . ?
C25A C26A C21A O1A 175.8(12) . . . . ?
C25A C26A C21A C22A 0.0 . . . . ?
C25A C24A C23A C22A 0.0 . . . . ?
C24A C23A C22A C21A 0.0 . . . . ?
C24A C23A C22A C17A -176.4(14) . . . . ?
C23A C22A C21A O1A -176.1(12) . . . . ?
C23A C22A C21A C26A 0.0 . . . . ?
C23A C22A C17A C16A -10(3) . . . . ?
C23A C22A C17A C18A 172.4(12) . . . . ?
C22A C17A C18A O1A 6.4(13) . . . . ?
C22A C17A C18A C19A 175.7(12) . . . . ?
C21A O1A C18A C17A -5.3(12) . . . . ?
C21A O1A C18A C19A -174.2(13) . . . . ?
C21A C26A C25A C24A 0.0 . . . . ?
C21A C22A C17A C16A 174(2) . . . . ?
C21A C22A C17A C18A -4.3(10) . . . . ?
C15A C16A C11A C12A 0.0 . . . . ?
C15A C16A C17A C22A -176.7(13) . . . . ?
C15A C16A C17A C18A 1(2) . . . . ?
C16A C15A C14A C13A 0.0 . . . . ?
C16A C15A C20A C19A 10(3) . . . . ?
C16A C11A C12A C13A 0.0 . . . . ?
C16A C17A C18A O1A -171.8(15) . . . . ?
C16A C17A C18A C19A -3(2) . . . . ?
C11A C16A C17A C22A 1(3) . . . . ?
C11A C16A C17A C18A 178.2(12) . . . . ?
C11A C12A C13A C14A 0.0 . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
C14A C15A C16A C11A 0.0 . . . . ?
C14A C15A C16A C17A 177.3(19) . . . . ?
C14A C15A C20A C19A -171.4(14) . . . . ?
C17A C22A C21A O1A 1.4(10) . . . . ?
C17A C22A C21A C26A 177.5(10) . . . . ?
C17A C16A C11A C12A -177.2(19) . . . . ?
C17A C18A C19A C20A 7.3(19) . . . . ?
C18A O1A C21A C26A -173.9(10) . . . . ?
C18A O1A C21A C22A 2.0(10) . . . . ?
C18A C19A C20A C15A -12(3) . . . . ?
C20A C15A C16A C11A 178(2) . . . . ?
C20A C15A C16A C17A -4.5(19) . . . . ?
C20A C15A C14A C13A -178(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
