# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_mpt8752_0m
_database_code_depnum_ccdc_archive 'CCDC 1849664'
loop_
_audit_author_name
_audit_author_address
'Zhang Chuanbao'
;Henan University
China
;
_audit_update_record             
;
2024-08-12 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_audit_creation_date             2024-08-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H16 F2 N4 O2'
_chemical_formula_sum            'C28 H16 F2 N4 O2'
_chemical_formula_weight         478.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.9992(9)
_cell_length_b                   11.0091(12)
_cell_length_c                   29.001(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.719(2)
_cell_angle_gamma                90
_cell_volume                     2871.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1884
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.762
_cell_measurement_theta_min      2.629
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0532 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.9238.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14496
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.099
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         2.323
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_source            'Incoatc Ius 3.0 '
_diffrn_source_type              Microfocus
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2607
_reflns_number_total             5097
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5097
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.010
_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)+(0.0682P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1498
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid bond restraints
 F1, C22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C18, C21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C34, C27
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Rotating group:
 N1(H1A,H1B)
4.b Ternary CH refined with riding coordinates:
 C16(H16), C29(H29)
4.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C26(H26), C35(H35), C23(H23), C21(H21), C20(H20), C24(H24),
 C27(H27), C25(H25), C30(H30), C34(H34), C33(H33)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O2 O 0.12450(15) 0.57981(13) 0.84010(5) 0.0610(4) Uani 1 1 d . . . . .
O1 O -0.1553(2) 0.35524(16) 0.84078(6) 0.0863(6) Uani 1 1 d . . . . .
F1 F -0.55991(17) 0.81491(17) 0.82148(7) 0.1285(7) Uani 1 1 d . U . . .
C36 C 0.2201(3) 0.4812(2) 0.93181(8) 0.0651(6) Uani 1 1 d . . . . .
N3 N 0.4582(3) 0.3883(2) 0.96701(9) 0.1072(9) Uani 1 1 d . . . . .
C6 C 0.3508(3) 0.4272(3) 0.95113(9) 0.0784(8) Uani 1 1 d . . . . .
C7 C 0.1797(3) 0.5897(2) 0.94931(8) 0.0685(7) Uani 1 1 d . . . . .
C9 C -0.1934(2) 0.6403(2) 0.87794(8) 0.0611(6) Uani 1 1 d . . . . .
C10 C -0.1816(3) 0.7148(2) 0.83951(8) 0.0688(7) Uani 1 1 d . . . . .
H10 H -0.089349 0.725817 0.826500 0.083 Uiso 1 1 calc R U . . .
N1 N 0.2524(3) 0.6480(2) 0.98470(8) 0.1008(8) Uani 1 1 d . . . . .
H1A H 0.346227 0.634819 0.982826 0.121 Uiso 1 1 d R U . . .
H1B H 0.235483 0.724739 0.982452 0.121 Uiso 1 1 d R U . . .
C12 C 0.0415(3) 0.6554(2) 0.93087(8) 0.0604(6) Uani 1 1 d . . . . .
N4 N 0.1318(3) 0.8546(2) 0.89072(8) 0.0890(7) Uani 1 1 d . . . . .
C14 C 0.0333(2) 0.4989(2) 0.86688(7) 0.0568(6) Uani 1 1 d . . . . .
C15 C -0.0460(3) 0.6968(2) 0.97047(10) 0.0746(7) Uani 1 1 d . . . . .
C16 C 0.1359(2) 0.4119(2) 0.89436(8) 0.0616(6) Uani 1 1 d . . . . .
H16 H 0.071272 0.354342 0.909954 0.074 Uiso 1 1 calc R U . . .
C18 C -0.0123(3) 0.4693(2) 0.78627(8) 0.0648(6) Uani 1 1 d . U . . .
C17 C 0.0971(3) 0.5547(2) 0.79428(8) 0.0599(6) Uani 1 1 d . . . . .
C26 C 0.1729(3) 0.6121(2) 0.75976(9) 0.0739(7) Uani 1 1 d . . . . .
H26 H 0.247823 0.668371 0.766144 0.089 Uiso 1 1 calc R U . . .
C35 C 0.1310(4) 0.5812(3) 0.71573(10) 0.0914(9) Uani 1 1 d . . . . .
H35 H 0.178487 0.618338 0.691414 0.110 Uiso 1 1 calc R U . . .
C23 C 0.0208(4) 0.4967(3) 0.70576(10) 0.0905(9) Uani 1 1 d . . . . .
H23 H -0.003839 0.478716 0.675147 0.109 Uiso 1 1 calc R U . . .
C21 C -0.0528(3) 0.4391(2) 0.74034(10) 0.0833(8) Uani 1 1 d . U . . .
H21 H -0.126661 0.382114 0.733693 0.100 Uiso 1 1 calc R U . . .
C19 C -0.0621(3) 0.4293(2) 0.83074(9) 0.0645(7) Uani 1 1 d . . . . .
C20 C -0.3050(3) 0.7729(2) 0.82034(9) 0.0783(7) Uani 1 1 d . . . . .
H20 H -0.296681 0.821584 0.794329 0.094 Uiso 1 1 calc R U . . .
C22 C -0.4380(3) 0.7577(3) 0.84015(12) 0.0861(8) Uani 1 1 d . U . . .
C24 C -0.3318(3) 0.6283(2) 0.89709(10) 0.0783(8) Uani 1 1 d . . . . .
H24 H -0.342098 0.579799 0.923048 0.094 Uiso 1 1 calc R U . . .
C27 C 0.3579(3) 0.3887(3) 0.84316(10) 0.0832(8) Uani 1 1 d . U . . .
H27 H 0.377350 0.471238 0.846626 0.100 Uiso 1 1 calc R U . . .
C8 C 0.2373(3) 0.3370(2) 0.86463(8) 0.0654(6) Uani 1 1 d . . . . .
C25 C 0.2131(3) 0.2136(3) 0.85970(11) 0.0919(9) Uani 1 1 d . . . . .
H25 H 0.133690 0.177722 0.874331 0.110 Uiso 1 1 calc R U . . .
C30 C 0.3040(4) 0.1430(3) 0.83363(14) 0.1221(12) Uani 1 1 d . U . . .
H30 H 0.287322 0.059907 0.830738 0.146 Uiso 1 1 calc R U . . .
C31 C 0.4175(4) 0.1961(4) 0.81237(13) 0.1169(12) Uani 1 1 d . . . . .
C34 C 0.4494(3) 0.3174(4) 0.81651(12) 0.1068(10) Uani 1 1 d . U . . .
H34 H 0.530219 0.351146 0.801872 0.128 Uiso 1 1 calc R U . . .
C29 C -0.0612(2) 0.5725(2) 0.89957(7) 0.0596(6) Uani 1 1 d . . . . .
H29 H -0.103964 0.512901 0.920500 0.072 Uiso 1 1 calc R U . . .
C32 C 0.0908(3) 0.7674(3) 0.90701(8) 0.0656(6) Uani 1 1 d . . . . .
C33 C -0.4545(3) 0.6872(3) 0.87827(12) 0.0940(9) Uani 1 1 d . . . . .
H33 H -0.546973 0.678900 0.891380 0.113 Uiso 1 1 calc R U . . .
N2 N -0.1116(3) 0.7280(2) 1.00122(9) 0.1051(8) Uani 1 1 d . . . . .
F2 F 0.5099(2) 0.1280(2) 0.78592(9) 0.1775(10) Uani 1 1 d . 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
O2 C14 1.451(2) . ?
O2 C17 1.373(3) . ?
O1 C19 1.212(3) . ?
F1 C22 1.363(3) . ?
C36 C6 1.418(4) . ?
C36 C7 1.352(3) . ?
C36 C16 1.512(3) . ?
N3 C6 1.141(3) . ?
C7 N1 1.361(3) . ?
C7 C12 1.522(3) . ?
C9 C10 1.391(3) . ?
C9 C24 1.385(3) . ?
C9 C29 1.523(3) . ?
C10 H10 0.9300 . ?
C10 C20 1.384(3) . ?
N1 H1A 0.8602 . ?
N1 H1B 0.8601 . ?
C12 C15 1.483(4) . ?
C12 C29 1.569(3) . ?
C12 C32 1.488(4) . ?
N4 C32 1.136(3) . ?
C14 C16 1.537(3) . ?
C14 C19 1.539(3) . ?
C14 C29 1.525(3) . ?
C15 N2 1.137(3) . ?
C16 H16 0.9800 . ?
C16 C8 1.518(3) . ?
C18 C17 1.376(3) . ?
C18 C21 1.410(3) . ?
C18 C19 1.447(3) . ?
C17 C26 1.381(3) . ?
C26 H26 0.9300 . ?
C26 C35 1.364(4) . ?
C35 H35 0.9300 . ?
C35 C23 1.384(4) . ?
C23 H23 0.9300 . ?
C23 C21 1.374(4) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C20 C22 1.354(4) . ?
C22 C33 1.363(4) . ?
C24 H24 0.9300 . ?
C24 C33 1.379(4) . ?
C27 H27 0.9300 . ?
C27 C8 1.389(3) . ?
C27 C34 1.389(4) . ?
C8 C25 1.383(3) . ?
C25 H25 0.9300 . ?
C25 C30 1.372(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.343(5) . ?
C31 C34 1.371(5) . ?
C31 F2 1.371(3) . ?
C34 H34 0.9300 . ?
C29 H29 0.9800 . ?
C33 H33 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
C17 O2 C14 107.84(17) . . ?
C6 C36 C16 117.6(2) . . ?
C7 C36 C6 116.8(2) . . ?
C7 C36 C16 125.5(2) . . ?
N3 C6 C36 177.3(3) . . ?
C36 C7 N1 124.8(2) . . ?
C36 C7 C12 120.9(2) . . ?
N1 C7 C12 114.2(2) . . ?
C10 C9 C29 122.8(2) . . ?
C24 C9 C10 117.9(2) . . ?
C24 C9 C29 119.3(2) . . ?
C9 C10 H10 119.5 . . ?
C20 C10 C9 121.0(2) . . ?
C20 C10 H10 119.5 . . ?
C7 N1 H1A 108.9 . . ?
C7 N1 H1B 109.0 . . ?
H1A N1 H1B 109.5 . . ?
C7 C12 C29 112.80(19) . . ?
C15 C12 C7 108.71(19) . . ?
C15 C12 C29 108.02(19) . . ?
C15 C12 C32 106.19(19) . . ?
C32 C12 C7 107.77(19) . . ?
C32 C12 C29 113.08(18) . . ?
O2 C14 C16 108.62(17) . . ?
O2 C14 C19 104.72(17) . . ?
O2 C14 C29 109.99(17) . . ?
C16 C14 C19 110.88(18) . . ?
C29 C14 C16 110.25(18) . . ?
C29 C14 C19 112.19(18) . . ?
N2 C15 C12 179.1(3) . . ?
C36 C16 C14 109.75(19) . . ?
C36 C16 H16 106.6 . . ?
C36 C16 C8 112.68(19) . . ?
C14 C16 H16 106.6 . . ?
C8 C16 C14 113.98(18) . . ?
C8 C16 H16 106.6 . . ?
C17 C18 C21 118.9(3) . . ?
C17 C18 C19 107.3(2) . . ?
C21 C18 C19 133.8(3) . . ?
O2 C17 C18 114.1(2) . . ?
O2 C17 C26 122.1(2) . . ?
C18 C17 C26 123.8(2) . . ?
C17 C26 H26 122.1 . . ?
C35 C26 C17 115.8(3) . . ?
C35 C26 H26 122.1 . . ?
C26 C35 H35 118.7 . . ?
C26 C35 C23 122.7(3) . . ?
C23 C35 H35 118.7 . . ?
C35 C23 H23 119.5 . . ?
C21 C23 C35 121.1(3) . . ?
C21 C23 H23 119.5 . . ?
C18 C21 H21 121.2 . . ?
C23 C21 C18 117.6(3) . . ?
C23 C21 H21 121.2 . . ?
O1 C19 C14 123.2(2) . . ?
O1 C19 C18 130.9(2) . . ?
C18 C19 C14 105.89(19) . . ?
C10 C20 H20 120.6 . . ?
C22 C20 C10 118.8(3) . . ?
C22 C20 H20 120.6 . . ?
C20 C22 F1 119.1(3) . . ?
C20 C22 C33 122.3(3) . . ?
C33 C22 F1 118.7(3) . . ?
C9 C24 H24 119.5 . . ?
C33 C24 C9 121.0(3) . . ?
C33 C24 H24 119.5 . . ?
C8 C27 H27 119.9 . . ?
C8 C27 C34 120.1(3) . . ?
C34 C27 H27 119.9 . . ?
C27 C8 C16 121.5(2) . . ?
C25 C8 C16 119.8(2) . . ?
C25 C8 C27 118.6(3) . . ?
C8 C25 H25 119.4 . . ?
C30 C25 C8 121.3(3) . . ?
C30 C25 H25 119.4 . . ?
C25 C30 H30 120.6 . . ?
C31 C30 C25 118.7(3) . . ?
C31 C30 H30 120.6 . . ?
C30 C31 C34 123.0(3) . . ?
C30 C31 F2 120.1(4) . . ?
F2 C31 C34 116.9(4) . . ?
C27 C34 H34 120.9 . . ?
C31 C34 C27 118.2(3) . . ?
C31 C34 H34 120.9 . . ?
C9 C29 C12 113.08(18) . . ?
C9 C29 C14 116.56(18) . . ?
C9 C29 H29 105.5 . . ?
C12 C29 H29 105.5 . . ?
C14 C29 C12 109.80(17) . . ?
C14 C29 H29 105.5 . . ?
N4 C32 C12 176.7(3) . . ?
C22 C33 C24 118.9(3) . . ?
C22 C33 H33 120.5 . . ?
C24 C33 H33 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C14 C16 C36 69.5(2) . . . . ?
O2 C14 C16 C8 -58.0(2) . . . . ?
O2 C14 C19 O1 -178.0(2) . . . . ?
O2 C14 C19 C18 3.5(2) . . . . ?
O2 C14 C29 C9 74.4(2) . . . . ?
O2 C14 C29 C12 -55.9(2) . . . . ?
O2 C17 C26 C35 -177.9(2) . . . . ?
F1 C22 C33 C24 179.5(2) . . . . ?
C36 C7 C12 C15 132.8(2) . . . . ?
C36 C7 C12 C29 13.0(3) . . . . ?
C36 C7 C12 C32 -112.5(2) . . . . ?
C36 C16 C8 C27 -53.5(3) . . . . ?
C36 C16 C8 C25 124.4(2) . . . . ?
C6 C36 C7 N1 -2.1(4) . . . . ?
C6 C36 C7 C12 179.8(2) . . . . ?
C6 C36 C16 C14 -160.9(2) . . . . ?
C6 C36 C16 C8 -32.7(3) . . . . ?
C7 C36 C16 C14 20.7(3) . . . . ?
C7 C36 C16 C8 148.8(2) . . . . ?
C7 C12 C29 C9 -175.48(18) . . . . ?
C7 C12 C29 C14 -43.4(2) . . . . ?
C9 C10 C20 C22 1.1(4) . . . . ?
C9 C24 C33 C22 0.2(4) . . . . ?
C10 C9 C24 C33 0.9(4) . . . . ?
C10 C9 C29 C12 78.8(3) . . . . ?
C10 C9 C29 C14 -49.9(3) . . . . ?
C10 C20 C22 F1 179.9(2) . . . . ?
C10 C20 C22 C33 0.0(4) . . . . ?
N1 C7 C12 C15 -45.5(3) . . . . ?
N1 C7 C12 C29 -165.3(2) . . . . ?
N1 C7 C12 C32 69.2(3) . . . . ?
C14 O2 C17 C18 4.2(2) . . . . ?
C14 O2 C17 C26 -176.5(2) . . . . ?
C14 C16 C8 C27 72.4(3) . . . . ?
C14 C16 C8 C25 -109.6(3) . . . . ?
C15 C12 C29 C9 64.3(2) . . . . ?
C15 C12 C29 C14 -163.58(19) . . . . ?
C16 C36 C7 N1 176.4(2) . . . . ?
C16 C36 C7 C12 -1.7(4) . . . . ?
C16 C14 C19 O1 65.1(3) . . . . ?
C16 C14 C19 C18 -113.5(2) . . . . ?
C16 C14 C29 C9 -165.89(18) . . . . ?
C16 C14 C29 C12 63.9(2) . . . . ?
C16 C8 C25 C30 -179.0(3) . . . . ?
C18 C17 C26 C35 1.3(4) . . . . ?
C17 O2 C14 C16 113.94(18) . . . . ?
C17 O2 C14 C19 -4.6(2) . . . . ?
C17 O2 C14 C29 -125.31(18) . . . . ?
C17 C18 C21 C23 0.3(4) . . . . ?
C17 C18 C19 O1 -179.6(2) . . . . ?
C17 C18 C19 C14 -1.2(2) . . . . ?
C17 C26 C35 C23 -0.7(4) . . . . ?
C26 C35 C23 C21 0.0(4) . . . . ?
C35 C23 C21 C18 0.2(4) . . . . ?
C21 C18 C17 O2 178.1(2) . . . . ?
C21 C18 C17 C26 -1.1(3) . . . . ?
C21 C18 C19 O1 0.5(5) . . . . ?
C21 C18 C19 C14 178.9(3) . . . . ?
C19 C14 C16 C36 -175.95(19) . . . . ?
C19 C14 C16 C8 56.6(2) . . . . ?
C19 C14 C29 C9 -41.8(3) . . . . ?
C19 C14 C29 C12 -172.00(18) . . . . ?
C19 C18 C17 O2 -1.8(3) . . . . ?
C19 C18 C17 C26 178.9(2) . . . . ?
C19 C18 C21 C23 -179.7(3) . . . . ?
C20 C22 C33 C24 -0.6(4) . . . . ?
C24 C9 C10 C20 -1.5(4) . . . . ?
C24 C9 C29 C12 -101.0(2) . . . . ?
C24 C9 C29 C14 130.4(2) . . . . ?
C27 C8 C25 C30 -1.0(4) . . . . ?
C8 C27 C34 C31 -0.3(5) . . . . ?
C8 C25 C30 C31 -0.6(5) . . . . ?
C25 C30 C31 C34 1.8(6) . . . . ?
C25 C30 C31 F2 -179.7(3) . . . . ?
C30 C31 C34 C27 -1.4(6) . . . . ?
C34 C27 C8 C16 179.4(2) . . . . ?
C34 C27 C8 C25 1.4(4) . . . . ?
C29 C9 C10 C20 178.7(2) . . . . ?
C29 C9 C24 C33 -179.4(2) . . . . ?
C29 C14 C16 C36 -51.1(2) . . . . ?
C29 C14 C16 C8 -178.53(19) . . . . ?
C29 C14 C19 O1 -58.7(3) . . . . ?
C29 C14 C19 C18 122.8(2) . . . . ?
C32 C12 C29 C9 -52.9(3) . . . . ?
C32 C12 C29 C14 79.2(2) . . . . ?
F2 C31 C34 C27 -179.9(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.435 0.000 0.000 341.1 83.1 ?
2 -0.579 0.500 0.500 341.1 83.1 ?
3 0.333 0.017 0.719 7.3 0.0 ?
4 0.333 0.483 0.219 7.3 0.0 ?
5 0.667 -0.017 0.281 7.3 0.0 ?
6 0.667 0.517 0.781 7.3 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_mo_hd_fjys1_0m
_database_code_depnum_ccdc_archive 'CCDC 2375476'
loop_
_audit_author_name
_audit_author_address
'Zhang Chuanbao'
;Henan University
China
;
_audit_update_record             
;
2024-08-05 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 N2 O3'
_chemical_formula_sum            'C28 H22 N2 O3'
_chemical_formula_weight         434.47

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   16.1597(16)
_cell_length_b                   10.6689(10)
_cell_length_c                   13.0214(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2245.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      30.60

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   0.7073
_exptl_transmission_factor_max   0.7462
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.700
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24137
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.909
_diffrn_reflns_theta_max         31.115
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6691
_reflns_number_gt                6160
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_max     0.900
_reflns_Friedel_fraction_full    0.998

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.3958P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2667 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6691
_refine_ls_number_parameters     312
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.07038(8) -0.05098(12) 0.48617(10) 0.0181(3) Uani 1 1 d . . . . .
H6 H 0.1208(18) -0.053(2) 0.470(2) 0.027 Uiso 1 1 d . U . . .
O2 O 0.05399(8) 0.26293(11) 0.15040(10) 0.0181(2) Uani 1 1 d . . . . .
O3 O 0.07060(10) 0.49209(14) 0.08577(10) 0.0250(3) Uani 1 1 d . . . . .
H9 H 0.0625(19) 0.412(3) 0.081(2) 0.037 Uiso 1 1 d . U . . .
N1 N -0.08758(10) -0.03694(15) 0.53539(13) 0.0217(3) Uani 1 1 d D . . . .
H7 H -0.1386(8) -0.045(2) 0.548(2) 0.033 Uiso 1 1 d D U . . .
H8 H -0.0573(14) -0.093(2) 0.562(2) 0.033 Uiso 1 1 d D U . . .
N2 N -0.26274(9) 0.12872(14) 0.46974(12) 0.0192(3) Uani 1 1 d . . . . .
C1 C -0.24702(13) 0.61825(17) 0.12840(17) 0.0254(4) Uani 1 1 d . . . . .
H15 H -0.2019 0.6778 0.1163 0.038 Uiso 1 1 calc R U . . .
H16 H -0.2903 0.6587 0.1694 0.038 Uiso 1 1 calc R U . . .
H1 H -0.2702 0.5914 0.0624 0.038 Uiso 1 1 calc R U . . .
C2 C -0.21410(11) 0.50546(17) 0.18552(14) 0.0184(3) Uani 1 1 d . . . . .
C3 C -0.18190(11) 0.40337(16) 0.13220(14) 0.0193(3) Uani 1 1 d . . . . .
H19 H -0.1880 0.3992 0.0597 0.023 Uiso 1 1 calc R U . . .
C4 C -0.14093(11) 0.30760(16) 0.18359(14) 0.0177(3) Uani 1 1 d . . . . .
H14 H -0.1191 0.2388 0.1460 0.021 Uiso 1 1 calc R U . . .
C5 C -0.13161(10) 0.31194(14) 0.29048(13) 0.0139(3) Uani 1 1 d . . . . .
C6 C -0.07741(10) 0.21956(14) 0.34351(13) 0.0130(3) Uani 1 1 d . . . . .
C7 C 0.00636(10) 0.21239(14) 0.31818(12) 0.0131(3) Uani 1 1 d . . . . .
C8 C 0.05894(10) 0.12232(15) 0.36430(12) 0.0126(3) Uani 1 1 d . . . . .
C9 C 0.14812(10) 0.11183(14) 0.33438(12) 0.0134(3) Uani 1 1 d . . . . .
C10 C 0.17216(10) 0.02801(16) 0.25790(13) 0.0164(3) Uani 1 1 d . . . . .
H5 H 0.1321 -0.0257 0.2276 0.020 Uiso 1 1 calc R U . . .
C11 C 0.25430(11) 0.02212(16) 0.22532(14) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.2693 -0.0346 0.1723 0.023 Uiso 1 1 calc R U . . .
C12 C 0.31439(11) 0.09810(17) 0.26936(15) 0.0200(3) Uani 1 1 d . . . . .
C13 C 0.40238(12) 0.0973(2) 0.22965(18) 0.0285(4) Uani 1 1 d . . . . .
H22 H 0.4188 0.0112 0.2133 0.043 Uiso 1 1 calc R U . . .
H2 H 0.4395 0.1313 0.2823 0.043 Uiso 1 1 calc R U . . .
H3 H 0.4059 0.1490 0.1676 0.043 Uiso 1 1 calc R U . . .
C14 C 0.02680(10) 0.04119(15) 0.43751(13) 0.0140(3) Uani 1 1 d . . . . .
C15 C -0.05795(10) 0.04581(15) 0.46543(13) 0.0140(3) Uani 1 1 d . . . . .
C16 C -0.10847(10) 0.13654(15) 0.41811(13) 0.0135(3) Uani 1 1 d . . . . .
C17 C 0.03888(9) 0.30188(14) 0.23827(13) 0.0130(3) Uani 1 1 d . . . . .
C18 C 0.05076(10) 0.43469(15) 0.26456(13) 0.0141(3) Uani 1 1 d . . . . .
C19 C 0.06735(11) 0.52361(16) 0.18620(14) 0.0184(3) Uani 1 1 d . . . . .
C20 C 0.08062(13) 0.64931(17) 0.21160(16) 0.0259(4) Uani 1 1 d . . . . .
H13 H 0.0920 0.7089 0.1592 0.031 Uiso 1 1 calc R U . . .
C21 C 0.07713(14) 0.68666(17) 0.31308(17) 0.0274(4) Uani 1 1 d . . . . .
H12 H 0.0872 0.7719 0.3301 0.033 Uiso 1 1 calc R U . . .
C22 C 0.05908(12) 0.60107(18) 0.39123(15) 0.0230(4) Uani 1 1 d . . . . .
H11 H 0.0558 0.6284 0.4606 0.028 Uiso 1 1 calc R U . . .
C23 C 0.04602(11) 0.47670(16) 0.36704(14) 0.0177(3) Uani 1 1 d . . . . .
H10 H 0.0337 0.4186 0.4202 0.021 Uiso 1 1 calc R U . . .
C24 C -0.21089(11) 0.50380(17) 0.29280(15) 0.0200(3) Uani 1 1 d . . . . .
H18 H -0.2372 0.5688 0.3305 0.024 Uiso 1 1 calc R U . . .
C25 C -0.16984(11) 0.40857(15) 0.34530(14) 0.0173(3) Uani 1 1 d . . . . .
H17 H -0.1678 0.4093 0.4182 0.021 Uiso 1 1 calc R U . . .
C26 C -0.19473(10) 0.13600(15) 0.44460(13) 0.0148(3) Uani 1 1 d . . . . .
C27 C 0.20879(10) 0.18506(16) 0.38162(14) 0.0179(3) Uani 1 1 d . . . . .
H21 H 0.1941 0.2404 0.4358 0.022 Uiso 1 1 calc R U . . .
C28 C 0.29114(11) 0.17711(17) 0.34943(15) 0.0210(3) Uani 1 1 d . . . . .
H20 H 0.3320 0.2265 0.3828 0.025 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 C14 1.3654(19) . ?
O1 H6 0.84(3) . ?
O2 C17 1.242(2) . ?
O3 C19 1.351(2) . ?
O3 H9 0.87(3) . ?
N1 C15 1.356(2) . ?
N1 H7 0.844(13) . ?
N1 H8 0.848(13) . ?
N2 C26 1.149(2) . ?
C1 C2 1.511(2) . ?
C1 H15 0.9800 . ?
C1 H16 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.392(3) . ?
C2 C24 1.398(3) . ?
C3 C4 1.389(2) . ?
C3 H19 0.9500 . ?
C4 C5 1.401(2) . ?
C4 H14 0.9500 . ?
C5 C25 1.398(2) . ?
C5 C6 1.488(2) . ?
C6 C7 1.395(2) . ?
C6 C16 1.407(2) . ?
C7 C8 1.416(2) . ?
C7 C17 1.507(2) . ?
C8 C14 1.388(2) . ?
C8 C9 1.497(2) . ?
C9 C10 1.394(2) . ?
C9 C27 1.396(2) . ?
C10 C11 1.395(2) . ?
C10 H5 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H4 0.9500 . ?
C12 C28 1.392(3) . ?
C12 C13 1.513(2) . ?
C13 H22 0.9800 . ?
C13 H2 0.9800 . ?
C13 H3 0.9800 . ?
C14 C15 1.418(2) . ?
C15 C16 1.408(2) . ?
C16 C26 1.436(2) . ?
C17 C18 1.470(2) . ?
C18 C23 1.410(2) . ?
C18 C19 1.419(2) . ?
C19 C20 1.398(2) . ?
C20 C21 1.381(3) . ?
C20 H13 0.9500 . ?
C21 C22 1.398(3) . ?
C21 H12 0.9500 . ?
C22 C23 1.380(2) . ?
C22 H11 0.9500 . ?
C23 H10 0.9500 . ?
C24 C25 1.393(2) . ?
C24 H18 0.9500 . ?
C25 H17 0.9500 . ?
C27 C28 1.398(2) . ?
C27 H21 0.9500 . ?
C28 H20 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
C14 O1 H6 113.4(18) . . ?
C19 O3 H9 108(2) . . ?
C15 N1 H7 122.4(18) . . ?
C15 N1 H8 122.0(18) . . ?
H7 N1 H8 115(2) . . ?
C2 C1 H15 109.5 . . ?
C2 C1 H16 109.5 . . ?
H15 C1 H16 109.5 . . ?
C2 C1 H1 109.5 . . ?
H15 C1 H1 109.5 . . ?
H16 C1 H1 109.5 . . ?
C3 C2 C24 118.32(17) . . ?
C3 C2 C1 120.60(17) . . ?
C24 C2 C1 120.99(17) . . ?
C4 C3 C2 120.88(16) . . ?
C4 C3 H19 119.6 . . ?
C2 C3 H19 119.6 . . ?
C3 C4 C5 120.37(16) . . ?
C3 C4 H14 119.8 . . ?
C5 C4 H14 119.8 . . ?
C25 C5 C4 118.96(15) . . ?
C25 C5 C6 120.76(15) . . ?
C4 C5 C6 120.16(15) . . ?
C7 C6 C16 118.34(14) . . ?
C7 C6 C5 119.84(14) . . ?
C16 C6 C5 121.81(14) . . ?
C6 C7 C8 121.26(14) . . ?
C6 C7 C17 117.83(13) . . ?
C8 C7 C17 120.90(14) . . ?
C14 C8 C7 119.32(14) . . ?
C14 C8 C9 119.49(14) . . ?
C7 C8 C9 121.19(14) . . ?
C10 C9 C27 118.56(15) . . ?
C10 C9 C8 120.15(14) . . ?
C27 C9 C8 121.29(14) . . ?
C9 C10 C11 120.76(16) . . ?
C9 C10 H5 119.6 . . ?
C11 C10 H5 119.6 . . ?
C12 C11 C10 120.90(16) . . ?
C12 C11 H4 119.6 . . ?
C10 C11 H4 119.6 . . ?
C11 C12 C28 118.28(16) . . ?
C11 C12 C13 120.85(18) . . ?
C28 C12 C13 120.85(17) . . ?
C12 C13 H22 109.5 . . ?
C12 C13 H2 109.5 . . ?
H22 C13 H2 109.5 . . ?
C12 C13 H3 109.5 . . ?
H22 C13 H3 109.5 . . ?
H2 C13 H3 109.5 . . ?
O1 C14 C8 125.07(14) . . ?
O1 C14 C15 113.85(14) . . ?
C8 C14 C15 121.04(14) . . ?
N1 C15 C16 122.46(15) . . ?
N1 C15 C14 119.39(15) . . ?
C16 C15 C14 118.15(14) . . ?
C6 C16 C15 121.87(14) . . ?
C6 C16 C26 120.97(14) . . ?
C15 C16 C26 117.06(14) . . ?
O2 C17 C18 120.76(14) . . ?
O2 C17 C7 119.53(13) . . ?
C18 C17 C7 119.70(14) . . ?
C23 C18 C19 118.58(15) . . ?
C23 C18 C17 121.31(15) . . ?
C19 C18 C17 120.11(15) . . ?
O3 C19 C20 117.50(16) . . ?
O3 C19 C18 122.48(16) . . ?
C20 C19 C18 120.02(17) . . ?
C21 C20 C19 119.79(17) . . ?
C21 C20 H13 120.1 . . ?
C19 C20 H13 120.1 . . ?
C20 C21 C22 121.09(17) . . ?
C20 C21 H12 119.5 . . ?
C22 C21 H12 119.5 . . ?
C23 C22 C21 119.60(17) . . ?
C23 C22 H11 120.2 . . ?
C21 C22 H11 120.2 . . ?
C22 C23 C18 120.89(17) . . ?
C22 C23 H10 119.6 . . ?
C18 C23 H10 119.6 . . ?
C25 C24 C2 121.16(17) . . ?
C25 C24 H18 119.4 . . ?
C2 C24 H18 119.4 . . ?
C24 C25 C5 119.86(16) . . ?
C24 C25 H17 120.1 . . ?
C5 C25 H17 120.1 . . ?
N2 C26 C16 175.47(18) . . ?
C9 C27 C28 120.16(16) . . ?
C9 C27 H21 119.9 . . ?
C28 C27 H21 119.9 . . ?
C12 C28 C27 121.21(16) . . ?
C12 C28 H20 119.4 . . ?
C27 C28 H20 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C24 C2 C3 C4 -5.7(3) . . . . ?
C1 C2 C3 C4 170.73(17) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C25 5.1(3) . . . . ?
C3 C4 C5 C6 -171.04(15) . . . . ?
C25 C5 C6 C7 -116.74(18) . . . . ?
C4 C5 C6 C7 59.3(2) . . . . ?
C25 C5 C6 C16 64.4(2) . . . . ?
C4 C5 C6 C16 -119.51(18) . . . . ?
C16 C6 C7 C8 1.4(2) . . . . ?
C5 C6 C7 C8 -177.54(14) . . . . ?
C16 C6 C7 C17 -179.94(14) . . . . ?
C5 C6 C7 C17 1.2(2) . . . . ?
C6 C7 C8 C14 -1.2(2) . . . . ?
C17 C7 C8 C14 -179.86(15) . . . . ?
C6 C7 C8 C9 177.86(15) . . . . ?
C17 C7 C8 C9 -0.8(2) . . . . ?
C14 C8 C9 C10 86.0(2) . . . . ?
C7 C8 C9 C10 -93.06(19) . . . . ?
C14 C8 C9 C27 -94.1(2) . . . . ?
C7 C8 C9 C27 86.8(2) . . . . ?
C27 C9 C10 C11 -3.4(2) . . . . ?
C8 C9 C10 C11 176.48(15) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 C28 2.3(3) . . . . ?
C10 C11 C12 C13 -176.27(17) . . . . ?
C7 C8 C14 O1 178.74(15) . . . . ?
C9 C8 C14 O1 -0.3(2) . . . . ?
C7 C8 C14 C15 1.1(2) . . . . ?
C9 C8 C14 C15 -178.03(15) . . . . ?
O1 C14 C15 N1 0.5(2) . . . . ?
C8 C14 C15 N1 178.40(17) . . . . ?
O1 C14 C15 C16 -179.01(14) . . . . ?
C8 C14 C15 C16 -1.1(2) . . . . ?
C7 C6 C16 C15 -1.4(2) . . . . ?
C5 C6 C16 C15 177.47(15) . . . . ?
C7 C6 C16 C26 -177.56(15) . . . . ?
C5 C6 C16 C26 1.3(2) . . . . ?
N1 C15 C16 C6 -178.20(17) . . . . ?
C14 C15 C16 C6 1.3(2) . . . . ?
N1 C15 C16 C26 -1.9(2) . . . . ?
C14 C15 C16 C26 177.55(15) . . . . ?
C6 C7 C17 O2 -104.83(18) . . . . ?
C8 C7 C17 O2 73.9(2) . . . . ?
C6 C7 C17 C18 73.94(19) . . . . ?
C8 C7 C17 C18 -107.36(17) . . . . ?
O2 C17 C18 C23 -170.29(16) . . . . ?
C7 C17 C18 C23 11.0(2) . . . . ?
O2 C17 C18 C19 9.7(2) . . . . ?
C7 C17 C18 C19 -169.02(15) . . . . ?
C23 C18 C19 O3 -178.06(17) . . . . ?
C17 C18 C19 O3 1.9(3) . . . . ?
C23 C18 C19 C20 1.6(3) . . . . ?
C17 C18 C19 C20 -178.45(17) . . . . ?
O3 C19 C20 C21 179.35(19) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C22 -1.1(3) . . . . ?
C20 C21 C22 C23 1.2(3) . . . . ?
C21 C22 C23 C18 0.1(3) . . . . ?
C19 C18 C23 C22 -1.5(3) . . . . ?
C17 C18 C23 C22 178.54(16) . . . . ?
C3 C2 C24 C25 5.9(3) . . . . ?
C1 C2 C24 C25 -170.55(17) . . . . ?
C2 C24 C25 C5 -0.6(3) . . . . ?
C4 C5 C25 C24 -4.9(2) . . . . ?
C6 C5 C25 C24 171.19(15) . . . . ?
C10 C9 C27 C28 2.5(3) . . . . ?
C8 C9 C27 C28 -177.43(16) . . . . ?
C11 C12 C28 C27 -3.2(3) . . . . ?
C13 C12 C28 C27 175.32(18) . . . . ?
C9 C27 C28 C12 0.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H8 O2 0.848(13) 2.147(19) 2.890(2) 146(2) 2
O3 H9 O2 0.87(3) 1.83(3) 2.5996(19) 146(3) .
O1 H6 N2 0.84(3) 2.05(3) 2.8295(19) 154(2) 4
N1 H8 O2 0.848(13) 2.147(19) 2.890(2) 146(2) 2
O3 H9 O2 0.87(3) 1.83(3) 2.5996(19) 146(3) .
O1 H6 N2 0.84(3) 2.05(3) 2.8295(19) 154(2) 4
N1 H8 O2 0.848(13) 2.147(19) 2.890(2) 146(2) 2
O3 H9 O2 0.87(3) 1.83(3) 2.5996(19) 146(3) .
O1 H6 N2 0.84(3) 2.05(3) 2.8295(19) 154(2) 4
N1 H8 O2 0.848(13) 2.147(19) 2.890(2) 146(2) 2
O3 H9 O2 0.87(3) 1.83(3) 2.5996(19) 146(3) .
O1 H6 N2 0.84(3) 2.05(3) 2.8295(19) 154(2) 4
O1 H6 N2 0.84(3) 2.05(3) 2.8295(19) 154(2) 4
O3 H9 O2 0.87(3) 1.83(3) 2.5996(19) 146(3) .
N1 H8 O2 0.848(13) 2.147(19) 2.890(2) 146(2) 2
O1 H6 N2 0.84(3) 2.05(3) 2.8295(19) 154(2) 4
O3 H9 O2 0.87(3) 1.83(3) 2.5996(19) 146(3) .
N1 H8 O2 0.848(13) 2.147(19) 2.890(2) 146(2) 2

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043



