# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_220729c
_database_code_depnum_ccdc_archive 'CCDC 2215794'
loop_
_audit_author_name
_audit_author_address
AA
;Guizhou university
China
;
_audit_update_record             
;
2022-10-27 deposited with the CCDC.	2023-06-16 downloaded from the CCDC.
;
_audit_creation_date             2022-10-27
_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         'C24 H15 N O2'
_chemical_formula_sum            'C24 H15 N O2'
_chemical_formula_weight         349.37
_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                   6.2451(8)
_cell_length_b                   14.9559(13)
_cell_length_c                   17.9000(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.281(2)
_cell_angle_gamma                90
_cell_volume                     1661.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1978
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.717
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7964
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.289
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1991
_reflns_number_total             2925
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.064
_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)+(0.0876P)²+1.1237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.1929
_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:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Fitted hexagon refined as free rotating group:
 C19(C20,C21,C22,C23,C24)
;
_atom_sites_solution_hydrogens   geom
_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
N1 N -0.1908(4) 0.94451(17) 0.31995(15) 0.0326(7) Uani 1 1 d . . . . .
O1 O -0.0910(4) 0.84377(16) 0.41354(14) 0.0465(7) Uani 1 1 d . . . . .
O2 O -0.2173(4) 1.02135(16) 0.20873(13) 0.0459(7) Uani 1 1 d . . . . .
C1 C -0.0736(5) 0.8728(2) 0.35221(19) 0.0312(8) Uani 1 1 d . . . . .
C2 C -0.1373(5) 0.9634(2) 0.24874(18) 0.0325(8) Uani 1 1 d . . . . .
C3 C 0.0338(5) 0.9012(2) 0.23513(18) 0.0309(8) Uani 1 1 d . . . . .
C4 C 0.0703(5) 0.8446(2) 0.29717(17) 0.0294(7) Uani 1 1 d . . . . .
C5 C 0.2281(5) 0.7814(2) 0.30176(17) 0.0292(7) Uani 1 1 d . . . . .
C6 C 0.3625(5) 0.7787(2) 0.24262(17) 0.0300(7) Uani 1 1 d . . . . .
C7 C 0.3236(6) 0.8372(2) 0.18026(18) 0.0335(8) Uani 1 1 d . . . . .
C8 C 0.1540(5) 0.8986(2) 0.17726(18) 0.0347(8) Uani 1 1 d . . . . .
H8 H 0.125126 0.936734 0.136335 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5357(5) 0.7191(2) 0.24349(18) 0.0346(8) Uani 1 1 d . . . . .
H9 H 0.562050 0.678879 0.283036 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6643(6) 0.7192(2) 0.1881(2) 0.0426(9) Uani 1 1 d . . . . .
H10 H 0.781577 0.680588 0.190714 0.051 Uiso 1 1 calc R U . . .
C11 C 0.6249(6) 0.7761(3) 0.1271(2) 0.0481(10) Uani 1 1 d . . . . .
H11 H 0.712968 0.774294 0.088458 0.058 Uiso 1 1 calc R U . . .
C12 C 0.4598(6) 0.8336(2) 0.1238(2) 0.0422(9) Uani 1 1 d . . . . .
H12 H 0.435671 0.872018 0.082847 0.051 Uiso 1 1 calc R U . . .
C13 C 0.2555(5) 0.7165(2) 0.36425(17) 0.0301(7) Uani 1 1 d . . . . .
C14 C 0.0968(6) 0.6550(2) 0.3712(2) 0.0402(9) Uani 1 1 d . . . . .
H14 H -0.027294 0.655565 0.337316 0.048 Uiso 1 1 calc R U . . .
C15 C 0.1187(7) 0.5928(2) 0.4271(2) 0.0490(10) Uani 1 1 d . . . . .
H15 H 0.010311 0.550991 0.431152 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2983(7) 0.5918(3) 0.4769(2) 0.0521(11) Uani 1 1 d . . . . .
H16 H 0.313298 0.549413 0.515124 0.063 Uiso 1 1 calc R U . . .
C17 C 0.4576(7) 0.6533(3) 0.4710(2) 0.0534(11) Uani 1 1 d . . . . .
H17 H 0.580629 0.652794 0.505280 0.064 Uiso 1 1 calc R U . . .
C18 C 0.4362(6) 0.7156(2) 0.41452(19) 0.0407(9) Uani 1 1 d . . . . .
H18 H 0.544924 0.757245 0.410476 0.049 Uiso 1 1 calc R U . . .
C19 C -0.3251(3) 0.99801(14) 0.35815(11) 0.0335(8) Uani 1 1 d G . . . .
C20 C -0.2485(3) 1.03671(16) 0.42648(12) 0.0424(9) Uani 1 1 d G . . . .
H20 H -0.108564 1.025247 0.447688 0.051 Uiso 1 1 calc R U . . .
C21 C -0.3811(4) 1.09255(16) 0.46313(11) 0.0520(11) Uani 1 1 d G . . . .
H21 H -0.329872 1.118440 0.508847 0.062 Uiso 1 1 calc R U . . .
C22 C -0.5903(4) 1.10968(15) 0.43143(14) 0.0559(11) Uani 1 1 d G . . . .
H22 H -0.679028 1.147038 0.455950 0.067 Uiso 1 1 calc R U . . .
C23 C -0.6669(3) 1.07098(17) 0.36310(15) 0.0543(11) Uani 1 1 d G . . . .
H23 H -0.806877 1.082443 0.341892 0.065 Uiso 1 1 calc R U . . .
C24 C -0.5343(3) 1.01514(15) 0.32645(11) 0.0460(9) Uani 1 1 d G . . . .
H24 H -0.585572 0.989250 0.280731 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.388(4) . ?
N1 C2 1.382(4) . ?
N1 C19 1.392(3) . ?
O1 C1 1.196(4) . ?
O2 C2 1.198(4) . ?
C1 C4 1.466(4) . ?
C2 C3 1.457(5) . ?
C3 C4 1.395(4) . ?
C3 C8 1.345(5) . ?
C4 C5 1.362(4) . ?
C5 C6 1.422(4) . ?
C5 C13 1.477(4) . ?
C6 C7 1.417(5) . ?
C6 C9 1.401(4) . ?
C7 C8 1.400(5) . ?
C7 C12 1.392(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.343(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.339(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(5) . ?
C13 C18 1.365(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.363(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.354(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.367(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.370(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.3900 . ?
C19 C24 1.3900 . ?
C20 H20 0.9300 . ?
C20 C21 1.3900 . ?
C21 H21 0.9300 . ?
C21 C22 1.3900 . ?
C22 H22 0.9300 . ?
C22 C23 1.3900 . ?
C23 H23 0.9300 . ?
C23 C24 1.3900 . ?
C24 H24 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
C1 N1 C19 124.0(3) . . ?
C2 N1 C1 111.9(3) . . ?
C2 N1 C19 123.7(2) . . ?
N1 C1 C4 106.1(3) . . ?
O1 C1 N1 124.4(3) . . ?
O1 C1 C4 129.5(3) . . ?
N1 C2 C3 106.2(3) . . ?
O2 C2 N1 124.9(3) . . ?
O2 C2 C3 128.9(3) . . ?
C4 C3 C2 108.3(3) . . ?
C8 C3 C2 128.9(3) . . ?
C8 C3 C4 122.7(3) . . ?
C3 C4 C1 107.5(3) . . ?
C5 C4 C1 130.7(3) . . ?
C5 C4 C3 121.6(3) . . ?
C4 C5 C6 117.2(3) . . ?
C4 C5 C13 121.7(3) . . ?
C6 C5 C13 121.1(3) . . ?
C7 C6 C5 120.4(3) . . ?
C9 C6 C5 121.8(3) . . ?
C9 C6 C7 117.8(3) . . ?
C8 C7 C6 119.9(3) . . ?
C12 C7 C6 118.9(3) . . ?
C12 C7 C8 121.2(3) . . ?
C3 C8 C7 118.2(3) . . ?
C3 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C6 C9 H9 119.5 . . ?
C10 C9 C6 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 120.9(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C5 119.0(3) . . ?
C18 C13 C5 121.7(3) . . ?
C18 C13 C14 119.3(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.9(4) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(4) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.0(4) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 N1 120.25(18) . . ?
C20 C19 C24 120.0 . . ?
C24 C19 N1 119.72(18) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 120.0 . . ?
C23 C24 C19 120.0 . . ?
C23 C24 H24 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C4 C3 0.5(3) . . . . ?
N1 C1 C4 C5 175.4(3) . . . . ?
N1 C2 C3 C4 2.6(3) . . . . ?
N1 C2 C3 C8 -172.7(3) . . . . ?
N1 C19 C20 C21 177.8(2) . . . . ?
N1 C19 C24 C23 -177.8(2) . . . . ?
O1 C1 C4 C3 -178.2(3) . . . . ?
O1 C1 C4 C5 -3.3(6) . . . . ?
O2 C2 C3 C4 -178.8(3) . . . . ?
O2 C2 C3 C8 6.0(6) . . . . ?
C1 N1 C2 O2 179.0(3) . . . . ?
C1 N1 C2 C3 -2.3(3) . . . . ?
C1 N1 C19 C20 52.1(3) . . . . ?
C1 N1 C19 C24 -130.1(3) . . . . ?
C1 C4 C5 C6 -170.7(3) . . . . ?
C1 C4 C5 C13 10.9(5) . . . . ?
C2 N1 C1 O1 179.9(3) . . . . ?
C2 N1 C1 C4 1.1(3) . . . . ?
C2 N1 C19 C20 -119.4(3) . . . . ?
C2 N1 C19 C24 58.4(3) . . . . ?
C2 C3 C4 C1 -1.9(3) . . . . ?
C2 C3 C4 C5 -177.3(3) . . . . ?
C2 C3 C8 C7 174.0(3) . . . . ?
C3 C4 C5 C6 3.5(4) . . . . ?
C3 C4 C5 C13 -174.8(3) . . . . ?
C4 C3 C8 C7 -0.7(5) . . . . ?
C4 C5 C6 C7 -3.1(4) . . . . ?
C4 C5 C6 C9 177.0(3) . . . . ?
C4 C5 C13 C14 65.4(4) . . . . ?
C4 C5 C13 C18 -115.5(4) . . . . ?
C5 C6 C7 C8 0.9(5) . . . . ?
C5 C6 C7 C12 179.2(3) . . . . ?
C5 C6 C9 C10 -178.2(3) . . . . ?
C5 C13 C14 C15 178.5(3) . . . . ?
C5 C13 C18 C17 -178.8(3) . . . . ?
C6 C5 C13 C14 -112.8(4) . . . . ?
C6 C5 C13 C18 66.2(4) . . . . ?
C6 C7 C8 C3 1.0(5) . . . . ?
C6 C7 C12 C11 0.4(5) . . . . ?
C6 C9 C10 C11 -2.3(5) . . . . ?
C7 C6 C9 C10 1.9(5) . . . . ?
C8 C3 C4 C1 173.7(3) . . . . ?
C8 C3 C4 C5 -1.7(5) . . . . ?
C8 C7 C12 C11 178.7(3) . . . . ?
C9 C6 C7 C8 -179.2(3) . . . . ?
C9 C6 C7 C12 -0.9(4) . . . . ?
C9 C10 C11 C12 1.8(6) . . . . ?
C10 C11 C12 C7 -0.8(6) . . . . ?
C12 C7 C8 C3 -177.3(3) . . . . ?
C13 C5 C6 C7 175.3(3) . . . . ?
C13 C5 C6 C9 -4.6(5) . . . . ?
C13 C14 C15 C16 0.4(6) . . . . ?
C14 C13 C18 C17 0.2(5) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C16 C17 C18 C13 0.2(6) . . . . ?
C18 C13 C14 C15 -0.5(5) . . . . ?
C19 N1 C1 O1 7.6(5) . . . . ?
C19 N1 C1 C4 -171.2(3) . . . . ?
C19 N1 C2 O2 -8.7(5) . . . . ?
C19 N1 C2 C3 170.0(2) . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C19 C24 C23 0.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C19 0.0 . . . . ?
C24 C19 C20 C21 0.0 . . . . ?

_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_20221031scy_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2216727'
loop_
_audit_author_name
_audit_author_address
bf
;Guizhou university
China
;
_audit_update_record             
;
2022-11-01 deposited with the CCDC.	2023-06-16 downloaded from the CCDC.
;
_audit_creation_date             2022-11-01
_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         'C25 H16 Br N O2'
_chemical_formula_sum            'C25 H16 Br N O2'
_chemical_formula_weight         442.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
H H 0.0000 0.0000 '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                   12.0668(11)
_cell_length_b                   9.0542(8)
_cell_length_c                   18.2899(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.926(3)
_cell_angle_gamma                90
_cell_volume                     1955.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      68.37
_cell_measurement_theta_min      4.90
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.034
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3298
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1659 before and 0.1176 after correction.
The Ratio of minimum to maximum transmission is 0.4379.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             833
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20852
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.583
_diffrn_reflns_theta_min         3.744
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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             0.055
_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                3106
_reflns_number_total             3560
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.149
_refine_diff_density_min         -1.819
_refine_diff_density_rms         0.166
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.360
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.1020
_refine_ls_restrained_S_all      1.360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2880
_refine_ls_wR_factor_ref         0.2996
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C13(H13), C14(H14), C16(H16), C18(H18), C19(H19), C20(H20),
 C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.75959(5) 0.74583(5) -0.00064(3) 0.0953(4) Uani 1 1 d . . . . .
C1 C 0.4624(3) 0.4792(4) -0.36072(17) 0.0607(8) Uani 1 1 d . . . . .
O1 O 0.2536(2) 0.4506(3) -0.25583(12) 0.0733(8) Uani 1 1 d . . . . .
C3 C 0.0798(2) 0.6480(3) -0.36537(14) 0.0519(7) Uani 1 1 d . . . . .
C4 C 0.1818(3) 0.6487(3) -0.40006(14) 0.0506(7) Uani 1 1 d . . . . .
N1 N 0.4170(2) 0.4268(3) -0.30101(14) 0.0600(7) Uani 1 1 d . . . . .
O2 O 0.5560(2) 0.4500(3) -0.36993(14) 0.0795(8) Uani 1 1 d . . . . .
C7 C 0.3726(3) 0.5712(3) -0.40535(15) 0.0533(7) Uani 1 1 d . . . . .
C8 C 0.3082(3) 0.4799(3) -0.30264(16) 0.0557(7) Uani 1 1 d . . . . .
C9 C 0.5684(3) 0.5770(4) -0.0689(2) 0.0737(9) Uani 1 1 d . . . . .
H9 H 0.537425 0.610606 -0.029434 0.088 Uiso 1 1 calc R U . . .
C10 C 0.1787(3) 0.7281(3) -0.46857(17) 0.0524(7) Uani 1 1 d . . . . .
C11 C 0.2791(2) 0.5737(3) -0.37057(14) 0.0497(7) Uani 1 1 d . . . . .
C12 C 0.0832(3) 0.8109(4) -0.50342(17) 0.0608(7) Uani 1 1 d . . . . .
H12 H 0.020546 0.816148 -0.481292 0.073 Uiso 1 1 calc R U . . .
C13 C -0.1150(3) 0.6518(4) -0.3069(2) 0.0741(10) Uani 1 1 d . . . . .
H13 H -0.180459 0.652934 -0.287481 0.089 Uiso 1 1 calc R U . . .
C14 C -0.0015(3) 0.5389(4) -0.3843(2) 0.0709(9) Uani 1 1 d . . . . .
H14 H 0.009278 0.463344 -0.416596 0.085 Uiso 1 1 calc R U . . .
C15 C 0.6764(3) 0.6202(4) -0.07460(19) 0.0680(9) Uani 1 1 d . . . . .
C16 C 0.3721(3) 0.6430(3) -0.47081(16) 0.0561(7) Uani 1 1 d . . . . .
H16 H 0.434576 0.639313 -0.493228 0.067 Uiso 1 1 calc R U . . .
C17 C 0.2752(3) 0.7225(4) -0.50341(16) 0.0570(8) Uani 1 1 d . . . . .
C18 C 0.0815(3) 0.8836(4) -0.56931(19) 0.0707(9) Uani 1 1 d . . . . .
H18 H 0.017470 0.936883 -0.591538 0.085 Uiso 1 1 calc R U . . .
C19 C 0.2688(3) 0.7996(4) -0.57137(17) 0.0637(8) Uani 1 1 d . . . . .
H19 H 0.330231 0.796476 -0.594802 0.076 Uiso 1 1 calc R U . . .
C20 C 0.0621(4) 0.7581(4) -0.3172(2) 0.0705(11) Uani 1 1 d . . . . .
H20 H 0.115535 0.832653 -0.304435 0.085 Uiso 1 1 calc R U . . .
C21 C 0.5519(3) 0.4338(3) -0.18079(17) 0.0590(8) Uani 1 1 d . . . . .
C22 C 0.6601(3) 0.4803(5) -0.1856(2) 0.0751(10) Uani 1 1 d . . . . .
H22 H 0.691374 0.447717 -0.225130 0.090 Uiso 1 1 calc R U . . .
C23 C 0.4812(3) 0.3383(4) -0.23996(18) 0.0669(9) Uani 1 1 d . . . . .
H23A H 0.530127 0.270651 -0.259587 0.080 Uiso 1 1 calc R U . . .
H23B H 0.429132 0.280199 -0.217786 0.080 Uiso 1 1 calc R U . . .
C24 C 0.1750(3) 0.8786(4) -0.60358(19) 0.0719(9) Uani 1 1 d . . . . .
H24 H 0.173172 0.928977 -0.648133 0.086 Uiso 1 1 calc R U . . .
C25 C -0.0987(3) 0.5421(5) -0.3554(2) 0.0814(11) Uani 1 1 d . . . . .
H25 H -0.153411 0.469234 -0.368851 0.098 Uiso 1 1 calc R U . . .
C26 C 0.5074(3) 0.4845(4) -0.1215(2) 0.0688(9) Uani 1 1 d . . . . .
H26 H 0.435071 0.455472 -0.117360 0.083 Uiso 1 1 calc R U . . .
C27 C -0.0352(4) 0.7589(4) -0.2873(3) 0.0797(12) Uani 1 1 d . . . . .
H27 H -0.045643 0.832646 -0.253938 0.096 Uiso 1 1 calc R U . . .
C29 C 0.7218(3) 0.5733(5) -0.1331(2) 0.0798(11) Uani 1 1 d . . . . .
H29 H 0.793672 0.604091 -0.137431 0.096 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
Br1 C15 1.890(4) . ?
C1 N1 1.402(4) . ?
C1 O2 1.205(4) . ?
C1 C7 1.472(5) . ?
O1 C8 1.212(4) . ?
C3 C4 1.496(4) . ?
C3 C14 1.385(4) . ?
C3 C20 1.376(4) . ?
C4 C10 1.438(4) . ?
C4 C11 1.368(4) . ?
N1 C8 1.393(4) . ?
N1 C23 1.460(4) . ?
C7 C11 1.406(4) . ?
C7 C16 1.361(4) . ?
C8 C11 1.486(4) . ?
C9 H9 0.9300 . ?
C9 C15 1.385(5) . ?
C9 C26 1.370(5) . ?
C10 C12 1.411(5) . ?
C10 C17 1.439(5) . ?
C12 H12 0.9300 . ?
C12 C18 1.370(5) . ?
C13 H13 0.9300 . ?
C13 C25 1.373(6) . ?
C13 C27 1.362(6) . ?
C14 H14 0.9300 . ?
C14 C25 1.383(6) . ?
C15 C29 1.367(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.397(5) . ?
C17 C19 1.414(4) . ?
C18 H18 0.9300 . ?
C18 C24 1.400(5) . ?
C19 H19 0.9300 . ?
C19 C24 1.366(5) . ?
C20 H20 0.9300 . ?
C20 C27 1.394(6) . ?
C21 C22 1.392(5) . ?
C21 C23 1.505(5) . ?
C21 C26 1.384(5) . ?
C22 H22 0.9300 . ?
C22 C29 1.374(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C29 H29 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
N1 C1 C7 105.2(3) . . ?
O2 C1 N1 124.2(3) . . ?
O2 C1 C7 130.5(3) . . ?
C14 C3 C4 119.9(3) . . ?
C20 C3 C4 121.3(3) . . ?
C20 C3 C14 118.7(3) . . ?
C10 C4 C3 119.8(3) . . ?
C11 C4 C3 123.0(3) . . ?
C11 C4 C10 117.2(3) . . ?
C1 N1 C23 123.4(3) . . ?
C8 N1 C1 112.6(3) . . ?
C8 N1 C23 123.7(3) . . ?
C11 C7 C1 109.0(2) . . ?
C16 C7 C1 128.8(3) . . ?
C16 C7 C11 122.2(3) . . ?
O1 C8 N1 123.8(3) . . ?
O1 C8 C11 130.3(3) . . ?
N1 C8 C11 105.9(2) . . ?
C15 C9 H9 120.1 . . ?
C26 C9 H9 120.1 . . ?
C26 C9 C15 119.8(3) . . ?
C4 C10 C17 119.4(3) . . ?
C12 C10 C4 122.0(3) . . ?
C12 C10 C17 118.6(3) . . ?
C4 C11 C7 122.3(3) . . ?
C4 C11 C8 130.5(3) . . ?
C7 C11 C8 107.2(3) . . ?
C10 C12 H12 119.5 . . ?
C18 C12 C10 121.0(3) . . ?
C18 C12 H12 119.5 . . ?
C25 C13 H13 120.1 . . ?
C27 C13 H13 120.1 . . ?
C27 C13 C25 119.8(3) . . ?
C3 C14 H14 119.9 . . ?
C25 C14 C3 120.1(3) . . ?
C25 C14 H14 119.9 . . ?
C9 C15 Br1 119.0(3) . . ?
C29 C15 Br1 120.6(3) . . ?
C29 C15 C9 120.4(4) . . ?
C7 C16 H16 120.9 . . ?
C7 C16 C17 118.2(3) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 C10 120.8(3) . . ?
C16 C17 C19 121.2(3) . . ?
C19 C17 C10 118.0(4) . . ?
C12 C18 H18 119.6 . . ?
C12 C18 C24 120.7(3) . . ?
C24 C18 H18 119.6 . . ?
C17 C19 H19 119.1 . . ?
C24 C19 C17 121.9(3) . . ?
C24 C19 H19 119.1 . . ?
C3 C20 H20 119.6 . . ?
C3 C20 C27 120.7(3) . . ?
C27 C20 H20 119.6 . . ?
C22 C21 C23 121.9(3) . . ?
C26 C21 C22 118.0(3) . . ?
C26 C21 C23 120.0(3) . . ?
C21 C22 H22 119.3 . . ?
C29 C22 C21 121.4(3) . . ?
C29 C22 H22 119.3 . . ?
N1 C23 C21 111.5(2) . . ?
N1 C23 H23A 109.3 . . ?
N1 C23 H23B 109.3 . . ?
C21 C23 H23A 109.3 . . ?
C21 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C18 C24 H24 120.1 . . ?
C19 C24 C18 119.8(3) . . ?
C19 C24 H24 120.1 . . ?
C13 C25 C14 120.6(3) . . ?
C13 C25 H25 119.7 . . ?
C14 C25 H25 119.7 . . ?
C9 C26 C21 121.0(4) . . ?
C9 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
C13 C27 C20 120.0(3) . . ?
C13 C27 H27 120.0 . . ?
C20 C27 H27 120.0 . . ?
C15 C29 C22 119.4(4) . . ?
C15 C29 H29 120.3 . . ?
C22 C29 H29 120.3 . . ?

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
Br1 C15 C29 C22 179.1(3) . . . . ?
C1 N1 C8 O1 -178.8(3) . . . . ?
C1 N1 C8 C11 1.1(3) . . . . ?
C1 N1 C23 C21 83.3(4) . . . . ?
C1 C7 C11 C4 -178.9(2) . . . . ?
C1 C7 C11 C8 -0.7(3) . . . . ?
C1 C7 C16 C17 179.0(3) . . . . ?
O1 C8 C11 C4 -2.3(5) . . . . ?
O1 C8 C11 C7 179.7(3) . . . . ?
C3 C4 C10 C12 2.3(4) . . . . ?
C3 C4 C10 C17 -177.1(3) . . . . ?
C3 C4 C11 C7 177.7(2) . . . . ?
C3 C4 C11 C8 -0.1(4) . . . . ?
C3 C14 C25 C13 -0.9(6) . . . . ?
C3 C20 C27 C13 -1.4(7) . . . . ?
C4 C3 C14 C25 -176.7(3) . . . . ?
C4 C3 C20 C27 177.7(4) . . . . ?
C4 C10 C12 C18 -178.9(3) . . . . ?
C4 C10 C17 C16 -1.1(5) . . . . ?
C4 C10 C17 C19 178.9(3) . . . . ?
N1 C1 C7 C11 1.3(3) . . . . ?
N1 C1 C7 C16 -177.2(3) . . . . ?
N1 C8 C11 C4 177.8(3) . . . . ?
N1 C8 C11 C7 -0.2(3) . . . . ?
O2 C1 N1 C8 178.6(3) . . . . ?
O2 C1 N1 C23 4.3(5) . . . . ?
O2 C1 C7 C11 -178.8(3) . . . . ?
O2 C1 C7 C16 2.6(6) . . . . ?
C7 C1 N1 C8 -1.5(4) . . . . ?
C7 C1 N1 C23 -175.8(3) . . . . ?
C7 C16 C17 C10 0.0(5) . . . . ?
C7 C16 C17 C19 -180.0(3) . . . . ?
C8 N1 C23 C21 -90.4(4) . . . . ?
C9 C15 C29 C22 -1.4(6) . . . . ?
C10 C4 C11 C7 -0.8(4) . . . . ?
C10 C4 C11 C8 -178.5(3) . . . . ?
C10 C12 C18 C24 -0.5(5) . . . . ?
C10 C17 C19 C24 0.5(5) . . . . ?
C11 C4 C10 C12 -179.2(3) . . . . ?
C11 C4 C10 C17 1.4(4) . . . . ?
C11 C7 C16 C17 0.7(4) . . . . ?
C12 C10 C17 C16 179.5(3) . . . . ?
C12 C10 C17 C19 -0.5(5) . . . . ?
C12 C18 C24 C19 0.5(6) . . . . ?
C14 C3 C4 C10 90.1(4) . . . . ?
C14 C3 C4 C11 -88.3(4) . . . . ?
C14 C3 C20 C27 0.7(6) . . . . ?
C15 C9 C26 C21 -0.3(6) . . . . ?
C16 C7 C11 C4 -0.3(4) . . . . ?
C16 C7 C11 C8 177.9(3) . . . . ?
C16 C17 C19 C24 -179.5(3) . . . . ?
C17 C10 C12 C18 0.5(5) . . . . ?
C17 C19 C24 C18 -0.5(6) . . . . ?
C20 C3 C4 C10 -86.8(4) . . . . ?
C20 C3 C4 C11 94.7(4) . . . . ?
C20 C3 C14 C25 0.4(6) . . . . ?
C21 C22 C29 C15 0.6(6) . . . . ?
C22 C21 C23 N1 -86.2(4) . . . . ?
C22 C21 C26 C9 -0.4(5) . . . . ?
C23 N1 C8 O1 -4.6(5) . . . . ?
C23 N1 C8 C11 175.4(3) . . . . ?
C23 C21 C22 C29 176.8(3) . . . . ?
C23 C21 C26 C9 -177.0(3) . . . . ?
C25 C13 C27 C20 0.8(7) . . . . ?
C26 C9 C15 Br1 -179.3(3) . . . . ?
C26 C9 C15 C29 1.2(6) . . . . ?
C26 C21 C22 C29 0.3(5) . . . . ?
C26 C21 C23 N1 90.2(4) . . . . ?
C27 C13 C25 C14 0.3(6) . . . . ?

_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_exp_7963
_database_code_depnum_ccdc_archive 'CCDC 2215798'
loop_
_audit_author_name
_audit_author_address
CA
;Guizhou university
China
;
_audit_update_record             
;
2022-10-27 deposited with the CCDC.	2023-06-16 downloaded from the CCDC.
;
_audit_creation_date             2022-10-27
_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         'C28 H18 N2 O4'
_chemical_formula_sum            'C28 H0.50 N2 O4'
_chemical_formula_weight         428.80
_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'
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'
H H 0.0000 0.0000 '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                   10.4064(7)
_cell_length_b                   12.1425(9)
_cell_length_c                   12.5679(9)
_cell_angle_alpha                113.686(7)
_cell_angle_beta                 91.428(5)
_cell_angle_gamma                104.951(6)
_cell_volume                     1390.15(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2687
_cell_measurement_temperature    114.3(2)
_cell_measurement_theta_max      28.0490
_cell_measurement_theta_min      3.5580
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.024
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             429
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.800
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11308
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.694
_diffrn_reflns_theta_min         3.256
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      114.3(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.800
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    4.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070   19.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega    3.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   37.0000  120.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00   19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -99.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -22.00    4.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -99.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00   33.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -57.0000  -60.0000 76

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00   82.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852 -178.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
  7 omega  -69.00    4.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -57.0000 -180.0000 73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0589358000
_diffrn_orient_matrix_UB_12      -0.0514228000
_diffrn_orient_matrix_UB_13      -0.0270744000
_diffrn_orient_matrix_UB_21      0.0277533000
_diffrn_orient_matrix_UB_22      -0.0367784000
_diffrn_orient_matrix_UB_23      0.0203698000
_diffrn_orient_matrix_UB_31      -0.0289953000
_diffrn_orient_matrix_UB_32      0.0212926000
_diffrn_orient_matrix_UB_33      0.0522699000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4036
_reflns_number_total             5737
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.057
_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)+(0.0862P)²+1.0625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1821
_refine_ls_wR_factor_ref         0.2034
_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.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C26(H26), C28(H28), C31(H31), C33(H33), C34(H34),
 C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43)
2.b Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4184(2) 0.21480(19) 0.43304(17) 0.0358(5) Uani 1 1 d . . . . .
O2 O 0.3809(2) -0.07927(19) 0.05708(18) 0.0413(5) Uani 1 1 d . . . . .
N1 N 0.4941(2) 0.0002(2) 0.2927(2) 0.0297(5) Uani 1 1 d . . . . .
O4 O 0.2502(2) -0.2296(2) 0.35574(19) 0.0400(5) Uani 1 1 d . . . . .
O3 O 0.2065(2) -0.0900(2) 0.2955(2) 0.0428(5) Uani 1 1 d . . . . .
N2 N 0.4294(2) 0.0640(2) 0.2516(2) 0.0288(5) Uani 1 1 d . . . . .
C10 C 0.2869(3) 0.1810(2) 0.2512(2) 0.0241(6) Uani 1 1 d . . . . .
C12 C 0.2165(3) 0.2676(2) 0.2773(2) 0.0248(6) Uani 1 1 d . . . . .
C13 C 0.1326(3) 0.2613(2) 0.1817(2) 0.0248(6) Uani 1 1 d . . . . .
C14 C 0.2798(3) 0.0907(2) 0.1350(2) 0.0246(6) Uani 1 1 d . . . . .
C16 C 0.1280(3) 0.1713(2) 0.0634(2) 0.0242(6) Uani 1 1 d . . . . .
C17 C 0.3824(3) 0.1633(2) 0.3294(2) 0.0264(6) Uani 1 1 d . . . . .
C19 C 0.7322(3) 0.0992(3) 0.2787(2) 0.0319(6) Uani 1 1 d . . . . .
H19 H 0.714048 0.153814 0.247280 0.038 Uiso 1 1 calc R U . . .
C20 C 0.0487(3) 0.3410(3) 0.1989(3) 0.0316(6) Uani 1 1 d . . . . .
H20 H 0.047177 0.399563 0.276304 0.038 Uiso 1 1 calc R U . . .
C21 C 0.3653(3) 0.0121(3) 0.1358(2) 0.0296(6) Uani 1 1 d . . . . .
C25 C 0.2248(3) 0.3638(3) 0.3998(2) 0.0283(6) Uani 1 1 d . . . . .
C26 C 0.2045(3) 0.0852(3) 0.0421(2) 0.0294(6) Uani 1 1 d . . . . .
H26 H 0.203155 0.025163 -0.035366 0.035 Uiso 1 1 calc R U . . .
C27 C 0.6305(3) 0.0186(3) 0.3049(2) 0.0281(6) Uani 1 1 d . . . . .
C28 C 0.0455(3) 0.1686(3) -0.0292(2) 0.0321(7) Uani 1 1 d . . . . .
H28 H 0.042994 0.109156 -0.107140 0.038 Uiso 1 1 calc R U . . .
C29 C 0.6545(3) -0.0643(3) 0.3498(2) 0.0300(6) Uani 1 1 d . . . . .
C31 C -0.0306(3) 0.2491(3) -0.0093(3) 0.0361(7) Uani 1 1 d . . . . .
H31 H -0.083777 0.247542 -0.072746 0.043 Uiso 1 1 calc R U . . .
C32 C 0.4309(3) -0.0939(3) 0.3279(2) 0.0284(6) Uani 1 1 d . . . . .
C33 C -0.0290(3) 0.3355(3) 0.1079(3) 0.0350(7) Uani 1 1 d . . . . .
H33 H -0.083481 0.390421 0.122625 0.042 Uiso 1 1 calc R U . . .
C34 C 0.7873(3) -0.0656(3) 0.3707(3) 0.0368(7) Uani 1 1 d . . . . .
H34 H 0.806559 -0.119781 0.402161 0.044 Uiso 1 1 calc R U . . .
C35 C 0.2853(3) -0.1350(3) 0.3235(2) 0.0317(6) Uani 1 1 d . . . . .
C36 C 0.5280(3) -0.1337(3) 0.3628(2) 0.0306(6) Uani 1 1 d . . . . .
H36 H 0.513780 -0.197110 0.390935 0.037 Uiso 1 1 calc R U . . .
C37 C 0.8892(3) 0.0138(3) 0.3446(3) 0.0408(8) Uani 1 1 d . . . . .
H37 H 0.979350 0.012802 0.356544 0.049 Uiso 1 1 calc R U . . .
C38 C 0.8617(3) 0.0955(3) 0.3009(3) 0.0381(7) Uani 1 1 d . . . . .
H38 H 0.934361 0.150570 0.285840 0.046 Uiso 1 1 calc R U . . .
C39 C 0.1894(3) 0.3265(3) 0.4891(2) 0.0351(7) Uani 1 1 d . . . . .
H39 H 0.160938 0.239711 0.472609 0.042 Uiso 1 1 calc R U . . .
C40 C 0.2677(3) 0.4917(3) 0.4268(3) 0.0348(7) Uani 1 1 d . . . . .
H40 H 0.293518 0.518210 0.366917 0.042 Uiso 1 1 calc R U . . .
C41 C 0.1958(3) 0.4166(3) 0.6024(3) 0.0428(8) Uani 1 1 d . . . . .
H41 H 0.171800 0.391089 0.663262 0.051 Uiso 1 1 calc R U . . .
C42 C 0.2367(3) 0.5423(3) 0.6267(3) 0.0441(8) Uani 1 1 d . . . . .
H42 H 0.239899 0.603364 0.704068 0.053 Uiso 1 1 calc R U . . .
C43 C 0.2733(3) 0.5800(3) 0.5388(3) 0.0446(8) Uani 1 1 d . . . . .
H43 H 0.302312 0.666974 0.555841 0.053 Uiso 1 1 calc R U . . .
C44 C 0.1076(3) -0.2809(3) 0.3516(3) 0.0453(8) Uani 1 1 d . . . . .
H44A H 0.063087 -0.318661 0.270240 0.068 Uiso 1 1 calc R U . . .
H44B H 0.070602 -0.213504 0.399856 0.068 Uiso 1 1 calc R U . . .
H44C H 0.092246 -0.345292 0.381929 0.068 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 C17 1.196(3) . ?
O2 C21 1.207(3) . ?
N1 N2 1.376(3) . ?
N1 C27 1.373(4) . ?
N1 C32 1.403(4) . ?
O4 C35 1.335(4) . ?
O4 C44 1.444(4) . ?
O3 C35 1.210(4) . ?
N2 C17 1.426(3) . ?
N2 C21 1.399(4) . ?
C10 C12 1.372(4) . ?
C10 C14 1.416(4) . ?
C10 C17 1.493(4) . ?
C12 C13 1.433(4) . ?
C12 C25 1.497(4) . ?
C13 C16 1.439(4) . ?
C13 C20 1.421(4) . ?
C14 C21 1.464(4) . ?
C14 C26 1.360(4) . ?
C16 C26 1.419(4) . ?
C16 C28 1.412(4) . ?
C19 H19 0.9500 . ?
C19 C27 1.389(4) . ?
C19 C38 1.385(4) . ?
C20 H20 0.9500 . ?
C20 C33 1.354(4) . ?
C25 C39 1.393(4) . ?
C25 C40 1.392(4) . ?
C26 H26 0.9500 . ?
C27 C29 1.405(4) . ?
C28 H28 0.9500 . ?
C28 C31 1.364(4) . ?
C29 C34 1.406(4) . ?
C29 C36 1.420(4) . ?
C31 H31 0.9500 . ?
C31 C33 1.420(4) . ?
C32 C35 1.460(4) . ?
C32 C36 1.359(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C34 C37 1.381(5) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C37 C38 1.394(5) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C39 C41 1.391(4) . ?
C40 H40 0.9500 . ?
C40 C43 1.373(4) . ?
C41 H41 0.9500 . ?
C41 C42 1.373(5) . ?
C42 H42 0.9500 . ?
C42 C43 1.384(5) . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C32 125.2(2) . . ?
C27 N1 N2 125.1(2) . . ?
C27 N1 C32 109.7(2) . . ?
C35 O4 C44 115.5(2) . . ?
N1 N2 C17 121.4(2) . . ?
N1 N2 C21 122.3(2) . . ?
C21 N2 C17 112.9(2) . . ?
C12 C10 C14 122.0(2) . . ?
C12 C10 C17 130.0(2) . . ?
C14 C10 C17 107.9(2) . . ?
C10 C12 C13 117.0(2) . . ?
C10 C12 C25 122.1(2) . . ?
C13 C12 C25 120.9(2) . . ?
C12 C13 C16 120.8(2) . . ?
C20 C13 C12 122.1(2) . . ?
C20 C13 C16 117.1(2) . . ?
C10 C14 C21 109.0(2) . . ?
C26 C14 C10 122.3(2) . . ?
C26 C14 C21 128.7(2) . . ?
C26 C16 C13 119.4(2) . . ?
C28 C16 C13 119.5(2) . . ?
C28 C16 C26 121.1(2) . . ?
O1 C17 N2 123.3(3) . . ?
O1 C17 C10 132.4(2) . . ?
N2 C17 C10 104.3(2) . . ?
C27 C19 H19 121.9 . . ?
C38 C19 H19 121.9 . . ?
C38 C19 C27 116.2(3) . . ?
C13 C20 H20 119.2 . . ?
C33 C20 C13 121.6(3) . . ?
C33 C20 H20 119.2 . . ?
O2 C21 N2 124.5(3) . . ?
O2 C21 C14 130.0(3) . . ?
N2 C21 C14 105.6(2) . . ?
C39 C25 C12 120.4(3) . . ?
C40 C25 C12 120.8(3) . . ?
C40 C25 C39 118.8(3) . . ?
C14 C26 C16 118.5(2) . . ?
C14 C26 H26 120.8 . . ?
C16 C26 H26 120.8 . . ?
N1 C27 C19 130.1(3) . . ?
N1 C27 C29 106.9(2) . . ?
C19 C27 C29 123.0(3) . . ?
C16 C28 H28 119.2 . . ?
C31 C28 C16 121.6(3) . . ?
C31 C28 H28 119.2 . . ?
C27 C29 C34 119.0(3) . . ?
C27 C29 C36 107.5(3) . . ?
C34 C29 C36 133.5(3) . . ?
C28 C31 H31 120.6 . . ?
C28 C31 C33 118.9(3) . . ?
C33 C31 H31 120.6 . . ?
N1 C32 C35 122.1(3) . . ?
C36 C32 N1 107.7(3) . . ?
C36 C32 C35 130.2(3) . . ?
C20 C33 C31 121.3(3) . . ?
C20 C33 H33 119.4 . . ?
C31 C33 H33 119.4 . . ?
C29 C34 H34 120.8 . . ?
C37 C34 C29 118.5(3) . . ?
C37 C34 H34 120.8 . . ?
O4 C35 C32 110.3(3) . . ?
O3 C35 O4 124.2(3) . . ?
O3 C35 C32 125.5(3) . . ?
C29 C36 H36 125.9 . . ?
C32 C36 C29 108.3(3) . . ?
C32 C36 H36 125.9 . . ?
C34 C37 H37 119.6 . . ?
C34 C37 C38 120.9(3) . . ?
C38 C37 H37 119.6 . . ?
C19 C38 C37 122.3(3) . . ?
C19 C38 H38 118.8 . . ?
C37 C38 H38 118.8 . . ?
C25 C39 H39 120.0 . . ?
C41 C39 C25 120.0(3) . . ?
C41 C39 H39 120.0 . . ?
C25 C40 H40 119.5 . . ?
C43 C40 C25 120.9(3) . . ?
C43 C40 H40 119.5 . . ?
C39 C41 H41 119.9 . . ?
C42 C41 C39 120.3(3) . . ?
C42 C41 H41 119.9 . . ?
C41 C42 H42 119.9 . . ?
C41 C42 C43 120.1(3) . . ?
C43 C42 H42 119.9 . . ?
C40 C43 C42 120.0(3) . . ?
C40 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
O4 C44 H44A 109.5 . . ?
O4 C44 H44B 109.5 . . ?
O4 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C17 O1 15.9(4) . . . . ?
N1 N2 C17 C10 -164.2(2) . . . . ?
N1 N2 C21 O2 -14.5(4) . . . . ?
N1 N2 C21 C14 165.0(2) . . . . ?
N1 C27 C29 C34 179.9(2) . . . . ?
N1 C27 C29 C36 0.7(3) . . . . ?
N1 C32 C35 O4 176.8(2) . . . . ?
N1 C32 C35 O3 -3.7(4) . . . . ?
N1 C32 C36 C29 0.0(3) . . . . ?
N2 N1 C27 C19 -1.2(4) . . . . ?
N2 N1 C27 C29 179.7(2) . . . . ?
N2 N1 C32 C35 0.4(4) . . . . ?
N2 N1 C32 C36 180.0(2) . . . . ?
C10 C12 C13 C16 -2.7(4) . . . . ?
C10 C12 C13 C20 176.1(3) . . . . ?
C10 C12 C25 C39 -58.6(4) . . . . ?
C10 C12 C25 C40 121.4(3) . . . . ?
C10 C14 C21 O2 175.1(3) . . . . ?
C10 C14 C21 N2 -4.4(3) . . . . ?
C10 C14 C26 C16 -1.6(4) . . . . ?
C12 C10 C14 C21 -179.9(2) . . . . ?
C12 C10 C14 C26 0.9(4) . . . . ?
C12 C10 C17 O1 3.3(5) . . . . ?
C12 C10 C17 N2 -176.6(3) . . . . ?
C12 C13 C16 C26 2.0(4) . . . . ?
C12 C13 C16 C28 -179.2(2) . . . . ?
C12 C13 C20 C33 179.1(3) . . . . ?
C12 C25 C39 C41 -179.2(3) . . . . ?
C12 C25 C40 C43 178.9(3) . . . . ?
C13 C12 C25 C39 120.6(3) . . . . ?
C13 C12 C25 C40 -59.3(4) . . . . ?
C13 C16 C26 C14 0.2(4) . . . . ?
C13 C16 C28 C31 -0.2(4) . . . . ?
C13 C20 C33 C31 0.3(5) . . . . ?
C14 C10 C12 C13 1.3(4) . . . . ?
C14 C10 C12 C25 -179.5(2) . . . . ?
C14 C10 C17 O1 -178.4(3) . . . . ?
C14 C10 C17 N2 1.8(3) . . . . ?
C16 C13 C20 C33 -2.0(4) . . . . ?
C16 C28 C31 C33 -1.6(4) . . . . ?
C17 N2 C21 O2 -173.8(3) . . . . ?
C17 N2 C21 C14 5.8(3) . . . . ?
C17 C10 C12 C13 179.4(3) . . . . ?
C17 C10 C12 C25 -1.3(4) . . . . ?
C17 C10 C14 C21 1.6(3) . . . . ?
C17 C10 C14 C26 -177.6(3) . . . . ?
C19 C27 C29 C34 0.7(4) . . . . ?
C19 C27 C29 C36 -178.5(2) . . . . ?
C20 C13 C16 C26 -176.8(2) . . . . ?
C20 C13 C16 C28 2.0(4) . . . . ?
C21 N2 C17 O1 175.4(3) . . . . ?
C21 N2 C17 C10 -4.8(3) . . . . ?
C21 C14 C26 C16 179.3(3) . . . . ?
C25 C12 C13 C16 178.0(2) . . . . ?
C25 C12 C13 C20 -3.2(4) . . . . ?
C25 C39 C41 C42 0.1(5) . . . . ?
C25 C40 C43 C42 0.4(5) . . . . ?
C26 C14 C21 O2 -5.8(5) . . . . ?
C26 C14 C21 N2 174.7(3) . . . . ?
C26 C16 C28 C31 178.6(3) . . . . ?
C27 N1 N2 C17 -102.6(3) . . . . ?
C27 N1 N2 C21 99.9(3) . . . . ?
C27 N1 C32 C35 -179.3(2) . . . . ?
C27 N1 C32 C36 0.4(3) . . . . ?
C27 C19 C38 C37 1.4(4) . . . . ?
C27 C29 C34 C37 -1.0(4) . . . . ?
C27 C29 C36 C32 -0.4(3) . . . . ?
C28 C16 C26 C14 -178.6(3) . . . . ?
C28 C31 C33 C20 1.6(5) . . . . ?
C29 C34 C37 C38 1.4(4) . . . . ?
C32 N1 N2 C17 77.8(3) . . . . ?
C32 N1 N2 C21 -79.7(3) . . . . ?
C32 N1 C27 C19 178.4(3) . . . . ?
C32 N1 C27 C29 -0.6(3) . . . . ?
C34 C29 C36 C32 -179.5(3) . . . . ?
C34 C37 C38 C19 -1.7(5) . . . . ?
C35 C32 C36 C29 179.7(3) . . . . ?
C36 C29 C34 C37 178.0(3) . . . . ?
C36 C32 C35 O4 -2.8(4) . . . . ?
C36 C32 C35 O3 176.8(3) . . . . ?
C38 C19 C27 N1 -179.8(3) . . . . ?
C38 C19 C27 C29 -0.9(4) . . . . ?
C39 C25 C40 C43 -1.0(5) . . . . ?
C39 C41 C42 C43 -0.8(5) . . . . ?
C40 C25 C39 C41 0.8(4) . . . . ?
C41 C42 C43 C40 0.5(5) . . . . ?
C44 O4 C35 O3 2.2(4) . . . . ?
C44 O4 C35 C32 -178.3(2) . . . . ?

_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 0.519 0.500 0.000 355.1 95.7 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
