# Supplementary Information (SI) for Chemical Science.
# 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. 
# 
#######################################################################

data_250114d_helei_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2435331'
loop_
_audit_author_name
_audit_author_address
Zetian
;Central China Normal University
China
;
_audit_update_record             
;
2025-03-31 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_audit_creation_date             2025-01-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            IPXZ
_chemical_name_systematic        IPXZ
_chemical_formula_moiety         'C18 H11 N O'
_chemical_formula_sum            'C18 H11 N O'
_chemical_formula_weight         257.28
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   15.0059(19)
_cell_length_b                   4.9727(6)
_cell_length_c                   16.534(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.643(5)
_cell_angle_gamma                90
_cell_volume                     1203.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3456
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      50.187
_cell_measurement_theta_min      3.14
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_T_max  0.7499
_exptl_absorpt_correction_T_min  0.5693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1587 before and 0.0880 after correction.
The Ratio of minimum to maximum transmission is 0.7592.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8253
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        50.223
_diffrn_reflns_theta_max         50.223
_diffrn_reflns_theta_min         3.136
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497929
_diffrn_source_voltage           69.97
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1418
_reflns_number_total             1825
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1825
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0806
_refine_ls_restrained_S_all      1.139
_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)+(0.0756P)²+3.7756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1995
_refine_ls_wR_factor_ref         0.2058
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.44560(18) 0.4180(6) 0.11814(16) 0.0179(7) Uani 1 1 d . . . . .
N1 N 0.5347(2) 0.4866(6) 0.28825(19) 0.0120(8) Uani 1 1 d . . . . .
C1 C 0.4235(3) 0.2629(8) 0.1822(2) 0.0140(10) Uani 1 1 d . . . . .
C2 C 0.3561(3) 0.0742(8) 0.1562(3) 0.0167(10) Uani 1 1 d . . . . .
H2 H 0.328239 0.059047 0.098996 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3289(3) -0.0935(9) 0.2131(3) 0.0195(10) Uani 1 1 d . . . . .
H3 H 0.282127 -0.222681 0.194999 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3699(3) -0.0725(9) 0.2962(3) 0.0181(10) Uani 1 1 d . . . . .
H4 H 0.351434 -0.187914 0.335318 0.022 Uiso 1 1 calc R U . . .
C5 C 0.4385(3) 0.1179(8) 0.3231(3) 0.0139(10) Uani 1 1 d . . . . .
H5 H 0.466615 0.130177 0.380298 0.017 Uiso 1 1 calc R U . . .
C6 C 0.4660(2) 0.2889(8) 0.2670(2) 0.0111(9) Uani 1 1 d . . . . .
C7 C 0.5562(2) 0.6358(8) 0.2239(2) 0.0119(9) Uani 1 1 d . . . . .
C8 C 0.6231(2) 0.8283(8) 0.2534(2) 0.0117(9) Uani 1 1 d . . . . .
C9 C 0.6519(3) 0.9962(8) 0.1958(2) 0.0157(10) Uani 1 1 d . . . . .
H9 H 0.696816 1.130864 0.213350 0.019 Uiso 1 1 calc R U . . .
C10 C 0.6127(3) 0.9597(9) 0.1126(2) 0.0164(10) Uani 1 1 d . . . . .
H10 H 0.632837 1.069299 0.073065 0.020 Uiso 1 1 calc R U . . .
C11 C 0.5446(3) 0.7673(8) 0.0843(2) 0.0155(10) Uani 1 1 d . . . . .
H11 H 0.518973 0.748282 0.026764 0.019 Uiso 1 1 calc R U . . .
C12 C 0.5153(2) 0.6066(8) 0.1412(2) 0.0128(9) Uani 1 1 d . . . . .
C13 C 0.6441(2) 0.7969(8) 0.3430(2) 0.0119(9) Uani 1 1 d . . . . .
C14 C 0.7049(3) 0.9313(8) 0.4066(2) 0.0152(10) Uani 1 1 d . . . . .
H14 H 0.742743 1.071501 0.394102 0.018 Uiso 1 1 calc R U . . .
C15 C 0.7090(3) 0.8568(9) 0.4877(2) 0.0186(10) Uani 1 1 d . . . . .
H15 H 0.749949 0.946458 0.531285 0.022 Uiso 1 1 calc R U . . .
C16 C 0.6536(3) 0.6512(9) 0.5063(2) 0.0174(10) Uani 1 1 d . . . . .
H16 H 0.657605 0.604080 0.562661 0.021 Uiso 1 1 calc R U . . .
C17 C 0.5927(3) 0.5127(9) 0.4448(2) 0.0152(10) Uani 1 1 d . . . . .
H17 H 0.555193 0.373392 0.458347 0.018 Uiso 1 1 calc R U . . .
C18 C 0.5886(2) 0.5855(8) 0.3627(2) 0.0105(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.407(5) . ?
O1 C12 1.395(5) . ?
N1 C6 1.412(5) . ?
N1 C7 1.392(5) . ?
N1 C18 1.406(5) . ?
C1 C2 1.377(6) . ?
C1 C6 1.414(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(6) . ?
C7 C8 1.396(5) . ?
C7 C12 1.378(6) . ?
C8 C9 1.404(6) . ?
C8 C13 1.455(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.404(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(6) . ?
C13 C14 1.402(6) . ?
C13 C18 1.422(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(5) . ?

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
C12 O1 C1 116.7(3) . . ?
C7 N1 C6 117.4(3) . . ?
C7 N1 C18 107.3(3) . . ?
C18 N1 C6 135.3(3) . . ?
O1 C1 C6 124.5(3) . . ?
C2 C1 O1 114.6(3) . . ?
C2 C1 C6 120.8(4) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.3(4) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
N1 C6 C1 117.2(3) . . ?
C5 C6 N1 124.7(3) . . ?
C5 C6 C1 118.1(4) . . ?
N1 C7 C8 111.6(3) . . ?
C12 C7 N1 125.1(4) . . ?
C12 C7 C8 123.3(4) . . ?
C7 C8 C9 118.4(4) . . ?
C7 C8 C13 105.1(3) . . ?
C9 C8 C13 136.5(4) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 118.0(4) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 118.6 . . ?
C9 C10 C11 122.7(4) . . ?
C11 C10 H10 118.6 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 O1 119.1(3) . . ?
C11 C12 O1 122.4(3) . . ?
C11 C12 C7 118.5(4) . . ?
C14 C13 C8 132.3(4) . . ?
C14 C13 C18 119.9(4) . . ?
C18 C13 C8 107.8(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 118.9(4) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.7(4) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 122.0(4) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 H17 121.1 . . ?
C16 C17 C18 117.7(4) . . ?
C18 C17 H17 121.1 . . ?
N1 C18 C13 108.2(3) . . ?
C17 C18 N1 131.0(4) . . ?
C17 C18 C13 120.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.2(3) . . . . ?
O1 C1 C6 N1 0.7(5) . . . . ?
O1 C1 C6 C5 -178.6(3) . . . . ?
N1 C7 C8 C9 -179.7(3) . . . . ?
N1 C7 C8 C13 -0.5(4) . . . . ?
N1 C7 C12 O1 1.2(6) . . . . ?
N1 C7 C12 C11 -179.4(4) . . . . ?
C1 O1 C12 C7 -1.8(5) . . . . ?
C1 O1 C12 C11 178.8(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C1 C6 N1 179.8(3) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C4 C5 C6 N1 -179.9(3) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C6 N1 C7 C8 178.5(3) . . . . ?
C6 N1 C7 C12 0.4(5) . . . . ?
C6 N1 C18 C13 -177.8(4) . . . . ?
C6 N1 C18 C17 1.0(7) . . . . ?
C6 C1 C2 C3 0.0(6) . . . . ?
C7 N1 C6 C1 -1.3(5) . . . . ?
C7 N1 C6 C5 177.9(3) . . . . ?
C7 N1 C18 C13 -0.3(4) . . . . ?
C7 N1 C18 C17 178.4(4) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C7 C8 C13 C14 -179.7(4) . . . . ?
C7 C8 C13 C18 0.2(4) . . . . ?
C8 C7 C12 O1 -176.6(3) . . . . ?
C8 C7 C12 C11 2.9(6) . . . . ?
C8 C9 C10 C11 1.6(6) . . . . ?
C8 C13 C14 C15 179.3(4) . . . . ?
C8 C13 C18 N1 0.1(4) . . . . ?
C8 C13 C18 C17 -178.8(3) . . . . ?
C9 C8 C13 C14 -0.8(7) . . . . ?
C9 C8 C13 C18 179.2(4) . . . . ?
C9 C10 C11 C12 -0.3(6) . . . . ?
C10 C11 C12 O1 177.6(3) . . . . ?
C10 C11 C12 C7 -1.8(6) . . . . ?
C12 O1 C1 C2 -178.2(3) . . . . ?
C12 O1 C1 C6 0.9(5) . . . . ?
C12 C7 C8 C9 -1.6(6) . . . . ?
C12 C7 C8 C13 177.6(3) . . . . ?
C13 C8 C9 C10 -179.5(4) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C14 C13 C18 N1 -180.0(3) . . . . ?
C14 C13 C18 C17 1.1(5) . . . . ?
C14 C15 C16 C17 0.2(6) . . . . ?
C15 C16 C17 C18 0.2(6) . . . . ?
C16 C17 C18 N1 -179.5(4) . . . . ?
C16 C17 C18 C13 -0.9(5) . . . . ?
C18 N1 C6 C1 175.9(4) . . . . ?
C18 N1 C6 C5 -4.9(6) . . . . ?
C18 N1 C7 C8 0.5(4) . . . . ?
C18 N1 C7 C12 -177.5(4) . . . . ?
C18 C13 C14 C15 -0.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wang
_database_code_depnum_ccdc_archive 'CCDC 2435332'
loop_
_audit_author_name
_audit_author_address
WANG
;Central China Normal University
China
;
_audit_update_record             
;
2025-03-31 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_audit_creation_date             2025-01-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            IPTZ
_chemical_name_systematic        IPTZ
_chemical_formula_moiety         'C18 H11 N S'
_chemical_formula_sum            'C18 H11 N S'
_chemical_formula_weight         273.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   16.2373(9)
_cell_length_b                   7.5960(4)
_cell_length_c                   20.7374(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2557.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.33
_cell_measurement_theta_min      5.89
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.769
_exptl_absorpt_coefficient_mu    1.388
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1382 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.7431.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            51876
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.341
_diffrn_reflns_theta_min         5.895
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3572
_reflns_number_total             3796
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.458
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      1.059
_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)+(0.0789P)²+3.8157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1607
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1 S 0.60455(3) 0.53556(6) 0.55394(2) 0.02314(15) Uani 1 1 d . . . . .
N1 N 0.66706(8) 0.6295(2) 0.69123(7) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.72984(10) 0.6004(2) 0.64502(8) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.81330(10) 0.6189(2) 0.65992(8) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.829182 0.654578 0.702033 0.022 Uiso 1 1 calc R U . . .
C3 C 0.87338(11) 0.5856(2) 0.61363(9) 0.0221(3) Uani 1 1 d . . . . .
H3 H 0.929971 0.594933 0.624739 0.027 Uiso 1 1 calc R U . . .
C4 C 0.85107(13) 0.5390(3) 0.55139(9) 0.0262(4) Uani 1 1 d . . . . .
H4 H 0.892142 0.513794 0.520104 0.031 Uiso 1 1 calc R U . . .
C5 C 0.76857(13) 0.5295(2) 0.53523(9) 0.0249(4) Uani 1 1 d . . . . .
H5 H 0.753314 0.503044 0.492079 0.030 Uiso 1 1 calc R U . . .
C6 C 0.70740(11) 0.5581(2) 0.58126(8) 0.0194(3) Uani 1 1 d . . . . .
C7 C 0.55346(11) 0.6650(2) 0.61147(9) 0.0198(3) Uani 1 1 d . . . . .
C8 C 0.47495(11) 0.7351(2) 0.60182(10) 0.0250(4) Uani 1 1 d . . . . .
H8 H 0.449570 0.726570 0.560665 0.030 Uiso 1 1 calc R U . . .
C9 C 0.43347(12) 0.8181(3) 0.65273(11) 0.0267(4) Uani 1 1 d . . . . .
H9 H 0.380287 0.866100 0.645273 0.032 Uiso 1 1 calc R U . . .
C10 C 0.46818(11) 0.8321(2) 0.71403(10) 0.0241(4) Uani 1 1 d . . . . .
H10 H 0.438548 0.884752 0.748495 0.029 Uiso 1 1 calc R U . . .
C11 C 0.54757(10) 0.7667(2) 0.72340(9) 0.0187(3) Uani 1 1 d . . . . .
C12 C 0.58920(10) 0.6865(2) 0.67151(8) 0.0161(3) Uani 1 1 d . . . . .
C13 C 0.60226(10) 0.7540(2) 0.77864(9) 0.0184(3) Uani 1 1 d . . . . .
C14 C 0.59277(12) 0.7997(2) 0.84356(10) 0.0228(4) Uani 1 1 d . . . . .
H14 H 0.544228 0.857402 0.857992 0.027 Uiso 1 1 calc R U . . .
C15 C 0.65559(12) 0.7593(3) 0.88656(9) 0.0247(4) Uani 1 1 d . . . . .
H15 H 0.650323 0.790869 0.930702 0.030 Uiso 1 1 calc R U . . .
C16 C 0.72665(12) 0.6724(3) 0.86529(9) 0.0220(3) Uani 1 1 d . . . . .
H16 H 0.768735 0.645161 0.895508 0.026 Uiso 1 1 calc R U . . .
C17 C 0.73713(10) 0.6249(2) 0.80109(8) 0.0181(3) Uani 1 1 d . . . . .
H17 H 0.785120 0.564120 0.787281 0.022 Uiso 1 1 calc R U . . .
C18 C 0.67493(10) 0.6693(2) 0.75749(8) 0.0164(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.7718(19) . ?
S1 C7 1.7547(19) . ?
N1 C1 1.416(2) . ?
N1 C12 1.398(2) . ?
N1 C18 1.413(2) . ?
C1 C2 1.397(2) . ?
C1 C6 1.409(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(3) . ?
C7 C8 1.396(2) . ?
C7 C12 1.383(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.402(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(2) . ?
C11 C12 1.409(2) . ?
C11 C13 1.453(2) . ?
C13 C14 1.399(3) . ?
C13 C18 1.414(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.401(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.397(2) . ?

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
C7 S1 C6 100.02(8) . . ?
C12 N1 C1 120.09(14) . . ?
C12 N1 C18 107.46(14) . . ?
C18 N1 C1 128.78(14) . . ?
C2 C1 N1 122.19(15) . . ?
C2 C1 C6 118.79(15) . . ?
C6 C1 N1 118.97(15) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.60(16) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.35(18) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.48(17) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.06(18) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 S1 124.47(14) . . ?
C5 C6 S1 115.94(14) . . ?
C5 C6 C1 119.59(17) . . ?
C8 C7 S1 123.23(15) . . ?
C12 C7 S1 118.66(13) . . ?
C12 C7 C8 117.86(17) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.15(18) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.76(17) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 120.9 . . ?
C9 C10 C11 118.25(18) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 C12 119.38(17) . . ?
C10 C11 C13 134.29(17) . . ?
C12 C11 C13 106.29(14) . . ?
N1 C12 C11 110.14(15) . . ?
C7 C12 N1 127.34(16) . . ?
C7 C12 C11 122.48(16) . . ?
C14 C13 C11 132.47(16) . . ?
C14 C13 C18 120.24(16) . . ?
C18 C13 C11 107.19(15) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.81(17) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.45(17) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.66(17) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 121.0 . . ?
C16 C17 C18 117.96(16) . . ?
C18 C17 H17 121.0 . . ?
N1 C18 C13 108.90(14) . . ?
C17 C18 N1 130.02(15) . . ?
C17 C18 C13 120.83(16) . . ?

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
S1 C7 C8 C9 171.79(14) . . . . ?
S1 C7 C12 N1 6.5(2) . . . . ?
S1 C7 C12 C11 -170.80(13) . . . . ?
N1 C1 C2 C3 178.63(16) . . . . ?
N1 C1 C6 S1 -0.7(2) . . . . ?
N1 C1 C6 C5 179.86(16) . . . . ?
C1 N1 C12 C7 23.8(3) . . . . ?
C1 N1 C12 C11 -158.65(15) . . . . ?
C1 N1 C18 C13 156.96(16) . . . . ?
C1 N1 C18 C17 -28.9(3) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
C2 C1 C6 S1 -178.28(13) . . . . ?
C2 C1 C6 C5 2.3(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 -3.0(3) . . . . ?
C4 C5 C6 S1 -178.34(15) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C6 S1 C7 C8 160.08(16) . . . . ?
C6 S1 C7 C12 -25.78(16) . . . . ?
C6 C1 C2 C3 -3.9(3) . . . . ?
C7 S1 C6 C1 23.88(17) . . . . ?
C7 S1 C6 C5 -156.69(14) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C7 C12 N1 -179.07(16) . . . . ?
C8 C7 C12 C11 3.7(3) . . . . ?
C8 C9 C10 C11 2.4(3) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C9 C10 C11 C13 -178.55(19) . . . . ?
C10 C11 C12 N1 -179.60(15) . . . . ?
C10 C11 C12 C7 -1.9(3) . . . . ?
C10 C11 C13 C14 2.3(3) . . . . ?
C10 C11 C13 C18 178.53(19) . . . . ?
C11 C13 C14 C15 175.42(18) . . . . ?
C11 C13 C18 N1 0.05(19) . . . . ?
C11 C13 C18 C17 -174.76(15) . . . . ?
C12 N1 C1 C2 151.56(16) . . . . ?
C12 N1 C1 C6 -25.9(2) . . . . ?
C12 N1 C18 C13 -0.99(18) . . . . ?
C12 N1 C18 C17 173.19(17) . . . . ?
C12 C7 C8 C9 -2.4(3) . . . . ?
C12 C11 C13 C14 -175.36(19) . . . . ?
C12 C11 C13 C18 0.89(19) . . . . ?
C13 C11 C12 N1 -1.53(19) . . . . ?
C13 C11 C12 C7 176.16(16) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C13 C18 N1 176.85(15) . . . . ?
C14 C13 C18 C17 2.0(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 N1 -175.93(17) . . . . ?
C16 C17 C18 C13 -2.3(3) . . . . ?
C18 N1 C1 C2 -4.0(3) . . . . ?
C18 N1 C1 C6 178.55(16) . . . . ?
C18 N1 C12 C7 -175.97(16) . . . . ?
C18 N1 C12 C11 1.58(18) . . . . ?
C18 C13 C14 C15 -0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wzt
_database_code_depnum_ccdc_archive 'CCDC 2435333'
loop_
_audit_author_name
_audit_author_address
WANG
;Central China Normal University
China
;
_audit_update_record             
;
2025-03-31 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_audit_creation_date             2025-01-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            IPSeZ
_chemical_name_systematic        IPSeZ
_chemical_formula_moiety         'C18 H11 N Se'
_chemical_formula_sum            'C18 H11 N Se'
_chemical_formula_weight         320.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -1.0833 0.8881 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A e a 2'
_space_group_name_Hall           'A 2 -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   16.3563(14)
_cell_length_b                   20.6009(17)
_cell_length_c                   7.9397(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2675.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    183.0
_cell_measurement_theta_max      60.23
_cell_measurement_theta_min      3.73
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.642
_exptl_absorpt_coefficient_mu    2.427
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.5841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1388 before and 0.0752 after correction.
The Ratio of minimum to maximum transmission is 0.7769.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13997
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.281
_diffrn_reflns_theta_min         3.733
_diffrn_ambient_temperature      183.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.913
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                2658
_reflns_number_total             2838
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.044(13)
_refine_ls_extinction_coef       0.0047(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2838
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.068
_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)+(0.0512P)²+0.9259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0922
_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:
 C003(H003), C007(H007), C008(H008), C00A(H00A), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se01 Se 0.60160(3) 0.55738(2) 0.65529(10) 0.0638(2) Uani 1 1 d . . . . .
N002 N 0.66735(17) 0.69722(13) 0.5460(4) 0.0453(6) Uani 1 1 d . . . . .
C003 C 0.8121(2) 0.66773(18) 0.5556(5) 0.0542(8) Uani 1 1 d . . . . .
H003 H 0.826278 0.709323 0.512953 0.065 Uiso 1 1 calc R U . . .
C004 C 0.6060(2) 0.78516(19) 0.4228(5) 0.0491(8) Uani 1 1 d . . . . .
C005 C 0.5518(2) 0.61883(17) 0.5093(4) 0.0517(8) Uani 1 1 d . . . . .
C006 C 0.7306(2) 0.65169(15) 0.5795(4) 0.0451(7) Uani 1 1 d . . . . .
C007 C 0.7272(3) 0.87205(18) 0.5109(6) 0.0608(10) Uani 1 1 d . . . . .
H007 H 0.768595 0.902493 0.539408 0.073 Uiso 1 1 calc R U . . .
C008 C 0.5974(2) 0.8504(2) 0.3802(6) 0.0592(10) Uani 1 1 d . . . . .
H008 H 0.550220 0.865014 0.321554 0.071 Uiso 1 1 calc R U . . .
C009 C 0.5516(2) 0.73013(18) 0.4072(4) 0.0486(7) Uani 1 1 d . . . . .
C00A C 0.4738(2) 0.7220(2) 0.3411(5) 0.0591(9) Uani 1 1 d . . . . .
H00A H 0.446345 0.756929 0.287336 0.071 Uiso 1 1 calc R U . . .
C00B C 0.5906(2) 0.67811(17) 0.4866(5) 0.0450(7) Uani 1 1 d . . . . .
C00C C 0.6760(2) 0.76409(16) 0.5087(4) 0.0460(7) Uani 1 1 d . . . . .
C00D C 0.6583(3) 0.89336(19) 0.4245(6) 0.0653(10) Uani 1 1 d . . . . .
H00D H 0.653115 0.937940 0.395737 0.078 Uiso 1 1 calc R U . . .
C00E C 0.4758(3) 0.6105(2) 0.4393(6) 0.0624(9) Uani 1 1 d . . . . .
H00E H 0.449341 0.569529 0.448180 0.075 Uiso 1 1 calc R U . . .
C00F C 0.8734(2) 0.6232(2) 0.5939(6) 0.0632(10) Uani 1 1 d . . . . .
H00F H 0.929132 0.634921 0.580044 0.076 Uiso 1 1 calc R U . . .
C00G C 0.7371(2) 0.80773(15) 0.5563(6) 0.0528(8) Uani 1 1 d . . . . .
H00G H 0.783795 0.793743 0.617627 0.063 Uiso 1 1 calc R U . . .
C00H C 0.4368(3) 0.6613(2) 0.3552(6) 0.0663(11) Uani 1 1 d . . . . .
H00H H 0.384337 0.654497 0.307030 0.080 Uiso 1 1 calc R U . . .
C00I C 0.7111(2) 0.58878(15) 0.6320(5) 0.0511(8) Uani 1 1 d . . . . .
C00J C 0.8537(3) 0.56249(18) 0.6512(9) 0.0698(11) Uani 1 1 d . . . . .
H00J H 0.895716 0.532602 0.679786 0.084 Uiso 1 1 calc R U . . .
C00K C 0.7731(3) 0.54491(17) 0.6675(7) 0.0644(10) Uani 1 1 d . . . . .
H00K H 0.759596 0.502238 0.703354 0.077 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
Se01 C005 1.900(4) . ?
Se01 C00I 1.914(4) . ?
N002 C006 1.422(4) . ?
N002 C00B 1.398(4) . ?
N002 C00C 1.416(4) . ?
C003 H003 0.9500 . ?
C003 C006 1.387(5) . ?
C003 C00F 1.392(5) . ?
C004 C008 1.392(6) . ?
C004 C009 1.447(5) . ?
C004 C00C 1.402(5) . ?
C005 C00B 1.388(5) . ?
C005 C00E 1.373(5) . ?
C006 C00I 1.398(5) . ?
C007 H007 0.9500 . ?
C007 C00D 1.391(7) . ?
C007 C00G 1.383(5) . ?
C008 H008 0.9500 . ?
C008 C00D 1.379(6) . ?
C009 C00A 1.387(5) . ?
C009 C00B 1.398(5) . ?
C00A H00A 0.9500 . ?
C00A C00H 1.392(6) . ?
C00C C00G 1.396(5) . ?
C00D H00D 0.9500 . ?
C00E H00E 0.9500 . ?
C00E C00H 1.397(7) . ?
C00F H00F 0.9500 . ?
C00F C00J 1.369(7) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00I C00K 1.387(5) . ?
C00J H00J 0.9500 . ?
C00J C00K 1.374(7) . ?
C00K H00K 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
C005 Se01 C00I 96.73(15) . . ?
C00B N002 C006 122.1(3) . . ?
C00B N002 C00C 107.1(3) . . ?
C00C N002 C006 127.4(3) . . ?
C006 C003 H003 119.8 . . ?
C006 C003 C00F 120.3(4) . . ?
C00F C003 H003 119.8 . . ?
C008 C004 C009 132.3(3) . . ?
C008 C004 C00C 120.0(4) . . ?
C00C C004 C009 107.6(3) . . ?
C00B C005 Se01 118.0(3) . . ?
C00E C005 Se01 123.5(3) . . ?
C00E C005 C00B 118.2(3) . . ?
C003 C006 N002 121.1(3) . . ?
C003 C006 C00I 118.7(3) . . ?
C00I C006 N002 120.1(3) . . ?
C00D C007 H007 119.1 . . ?
C00G C007 H007 119.1 . . ?
C00G C007 C00D 121.7(4) . . ?
C004 C008 H008 120.5 . . ?
C00D C008 C004 119.0(4) . . ?
C00D C008 H008 120.5 . . ?
C00A C009 C004 133.8(4) . . ?
C00A C009 C00B 119.8(3) . . ?
C00B C009 C004 106.3(3) . . ?
C009 C00A H00A 120.8 . . ?
C009 C00A C00H 118.5(4) . . ?
C00H C00A H00A 120.8 . . ?
N002 C00B C009 110.3(3) . . ?
C005 C00B N002 127.9(3) . . ?
C005 C00B C009 121.6(3) . . ?
C004 C00C N002 108.7(3) . . ?
C00G C00C N002 129.9(3) . . ?
C00G C00C C004 121.1(3) . . ?
C007 C00D H00D 119.7 . . ?
C008 C00D C007 120.6(4) . . ?
C008 C00D H00D 119.7 . . ?
C005 C00E H00E 119.6 . . ?
C005 C00E C00H 120.8(4) . . ?
C00H C00E H00E 119.6 . . ?
C003 C00F H00F 119.8 . . ?
C00J C00F C003 120.4(4) . . ?
C00J C00F H00F 119.8 . . ?
C007 C00G C00C 117.5(4) . . ?
C007 C00G H00G 121.2 . . ?
C00C C00G H00G 121.2 . . ?
C00A C00H C00E 120.9(4) . . ?
C00A C00H H00H 119.6 . . ?
C00E C00H H00H 119.6 . . ?
C006 C00I Se01 123.8(3) . . ?
C00K C00I Se01 116.4(3) . . ?
C00K C00I C006 119.9(3) . . ?
C00F C00J H00J 120.1 . . ?
C00F C00J C00K 119.8(3) . . ?
C00K C00J H00J 120.1 . . ?
C00I C00K H00K 119.6 . . ?
C00J C00K C00I 120.7(4) . . ?
C00J C00K H00K 119.6 . . ?

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
Se01 C005 C00B N002 6.5(5) . . . . ?
Se01 C005 C00B C009 -168.1(3) . . . . ?
Se01 C005 C00E C00H 169.7(3) . . . . ?
Se01 C00I C00K C00J 178.7(4) . . . . ?
N002 C006 C00I Se01 2.4(5) . . . . ?
N002 C006 C00I C00K -178.8(4) . . . . ?
N002 C00C C00G C007 -175.6(4) . . . . ?
C003 C006 C00I Se01 -175.5(3) . . . . ?
C003 C006 C00I C00K 3.4(6) . . . . ?
C003 C00F C00J C00K 1.5(8) . . . . ?
C004 C008 C00D C007 -0.2(7) . . . . ?
C004 C009 C00A C00H -176.6(4) . . . . ?
C004 C009 C00B N002 -1.8(4) . . . . ?
C004 C009 C00B C005 173.7(3) . . . . ?
C004 C00C C00G C007 -2.0(6) . . . . ?
C005 C00E C00H C00A -0.4(7) . . . . ?
C006 N002 C00B C005 26.5(6) . . . . ?
C006 N002 C00B C009 -158.3(3) . . . . ?
C006 N002 C00C C004 157.5(3) . . . . ?
C006 N002 C00C C00G -28.3(6) . . . . ?
C006 C003 C00F C00J 1.7(7) . . . . ?
C006 C00I C00K C00J -0.2(7) . . . . ?
C008 C004 C009 C00A 2.3(7) . . . . ?
C008 C004 C009 C00B -174.3(4) . . . . ?
C008 C004 C00C N002 176.3(3) . . . . ?
C008 C004 C00C C00G 1.5(6) . . . . ?
C009 C004 C008 C00D 174.2(4) . . . . ?
C009 C004 C00C N002 0.5(4) . . . . ?
C009 C004 C00C C00G -174.3(3) . . . . ?
C009 C00A C00H C00E 2.3(7) . . . . ?
C00A C009 C00B N002 -179.0(3) . . . . ?
C00A C009 C00B C005 -3.5(5) . . . . ?
C00B N002 C006 C003 147.2(3) . . . . ?
C00B N002 C006 C00I -30.5(5) . . . . ?
C00B N002 C00C C004 -1.6(4) . . . . ?
C00B N002 C00C C00G 172.6(4) . . . . ?
C00B C005 C00E C00H -3.3(6) . . . . ?
C00B C009 C00A C00H -0.4(6) . . . . ?
C00C N002 C006 C003 -9.1(5) . . . . ?
C00C N002 C006 C00I 173.2(3) . . . . ?
C00C N002 C00B C005 -173.0(4) . . . . ?
C00C N002 C00B C009 2.2(4) . . . . ?
C00C C004 C008 C00D -0.3(6) . . . . ?
C00C C004 C009 C00A 177.4(4) . . . . ?
C00C C004 C009 C00B 0.8(4) . . . . ?
C00D C007 C00G C00C 1.5(6) . . . . ?
C00E C005 C00B N002 180.0(4) . . . . ?
C00E C005 C00B C009 5.3(6) . . . . ?
C00F C003 C006 N002 178.1(3) . . . . ?
C00F C003 C006 C00I -4.1(6) . . . . ?
C00F C00J C00K C00I -2.3(9) . . . . ?
C00G C007 C00D C008 -0.4(7) . . . . ?
C00I Se01 C005 C00B -25.2(3) . . . . ?
C00I Se01 C005 C00E 161.7(4) . . . . ?

_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_shu
_database_code_depnum_ccdc_archive 'CCDC 2435337'
loop_
_audit_author_name
_audit_author_address
WANG
;Central China Normal University
China
;
_audit_update_record             
;
2025-03-31 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_audit_creation_date             2025-03-31
_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            CAZ-Ph-IPXZ
_chemical_name_systematic        CAZ-Ph-IPXZ
_chemical_formula_moiety         'C36 H22 N2 O'
_chemical_formula_sum            'C36 H22 N2 O'
_chemical_formula_weight         498.55
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   33.257(4)
_cell_length_b                   7.2429(7)
_cell_length_c                   20.523(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.653(4)
_cell_angle_gamma                90
_cell_volume                     4899.6(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9524
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.282
_cell_measurement_theta_min      5.439
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1084 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.7623.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            45739
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.311
_diffrn_reflns_theta_min         5.440
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.200057
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6974
_reflns_number_total             7228
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (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         0.341
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         7228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.024
_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)+(0.0573P)²+2.9733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1121
_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:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C24(H24), C26(H26), C27(H27),
  C28(H28), C29(H29), C33(H33), C34(H34), C35(H35), C36(H36)
;
_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
O1 O 0.56698(2) 0.65079(10) 0.38973(3) 0.02604(14) Uani 1 1 d . . . . .
N1 N 0.53852(2) 0.77776(10) 0.50593(3) 0.01958(14) Uani 1 1 d . . . . .
N2 N 0.33393(2) 0.62891(11) 0.72630(4) 0.02155(14) Uani 1 1 d . . . . .
C1 C 0.52601(3) 0.64517(12) 0.39587(4) 0.02253(16) Uani 1 1 d . . . . .
C2 C 0.49737(3) 0.57717(13) 0.34698(4) 0.02639(18) Uani 1 1 d . . . . .
H2 H 0.505134 0.535417 0.306589 0.032 Uiso 1 1 calc R U . . .
C3 C 0.45630(3) 0.57046(13) 0.35780(4) 0.02689(18) Uani 1 1 d . . . . .
H3 H 0.436686 0.524154 0.323845 0.032 Uiso 1 1 calc R U . . .
C4 C 0.44346(3) 0.62894(12) 0.41618(4) 0.02394(17) Uani 1 1 d . . . . .
H4 H 0.415695 0.622341 0.422374 0.029 Uiso 1 1 calc R U . . .
C5 C 0.47285(3) 0.69815(11) 0.46574(4) 0.01992(15) Uani 1 1 d . . . . .
C6 C 0.51302(3) 0.70501(11) 0.45342(4) 0.02015(15) Uani 1 1 d . . . . .
C7 C 0.59177(3) 0.74963(12) 0.43764(4) 0.02310(17) Uani 1 1 d . . . . .
C8 C 0.63064(3) 0.78634(14) 0.42381(5) 0.02820(19) Uani 1 1 d . . . . .
H8 H 0.638878 0.743557 0.383877 0.034 Uiso 1 1 calc R U . . .
C9 C 0.65762(3) 0.88546(16) 0.46812(5) 0.0312(2) Uani 1 1 d . . . . .
H9 H 0.684292 0.909995 0.458613 0.037 Uiso 1 1 calc R U . . .
C10 C 0.64549(3) 0.94850(15) 0.52627(5) 0.02895(19) Uani 1 1 d . . . . .
H10 H 0.663933 1.015864 0.556710 0.035 Uiso 1 1 calc R U . . .
C11 C 0.60620(3) 0.91316(13) 0.54019(4) 0.02356(17) Uani 1 1 d . . . . .
H11 H 0.598034 0.958162 0.579883 0.028 Uiso 1 1 calc R U . . .
C12 C 0.57892(3) 0.81290(12) 0.49662(4) 0.02042(16) Uani 1 1 d . . . . .
C13 C 0.51458(2) 0.81975(11) 0.55496(4) 0.01852(15) Uani 1 1 d . . . . .
C14 C 0.47373(2) 0.76974(11) 0.53198(4) 0.01843(15) Uani 1 1 d . . . . .
C15 C 0.44364(2) 0.79167(11) 0.57284(4) 0.01886(15) Uani 1 1 d . . . . .
H15 H 0.416474 0.756105 0.557960 0.023 Uiso 1 1 calc R U . . .
C16 C 0.45371(2) 0.86609(11) 0.63560(4) 0.01872(15) Uani 1 1 d . . . . .
C17 C 0.49422(3) 0.91763(12) 0.65624(4) 0.02121(16) Uani 1 1 d . . . . .
H17 H 0.500775 0.971102 0.698587 0.025 Uiso 1 1 calc R U . . .
C18 C 0.52498(3) 0.89391(12) 0.61757(4) 0.02088(16) Uani 1 1 d . . . . .
H18 H 0.552195 0.927071 0.633212 0.025 Uiso 1 1 calc R U . . .
C19 C 0.42225(2) 0.88926(11) 0.67999(4) 0.01868(15) Uani 1 1 d . . . . .
C20 C 0.42082(3) 1.04646(12) 0.71952(4) 0.02052(15) Uani 1 1 d . . . . .
H20 H 0.441125 1.138798 0.719684 0.025 Uiso 1 1 calc R U . . .
C21 C 0.38993(3) 1.06867(12) 0.75859(4) 0.02209(16) Uani 1 1 d . . . . .
H21 H 0.389115 1.176888 0.784539 0.027 Uiso 1 1 calc R U . . .
C22 C 0.36022(3) 0.93344(12) 0.75991(4) 0.02224(16) Uani 1 1 d . . . . .
H22 H 0.338774 0.949994 0.785642 0.027 Uiso 1 1 calc R U . . .
C23 C 0.36253(2) 0.77354(12) 0.72281(4) 0.02013(15) Uani 1 1 d . . . . .
C24 C 0.39310(2) 0.75122(11) 0.68312(4) 0.01970(15) Uani 1 1 d . . . . .
H24 H 0.394164 0.641539 0.658022 0.024 Uiso 1 1 calc R U . . .
C25 C 0.31005(2) 0.54677(12) 0.67320(4) 0.02177(16) Uani 1 1 d . . . . .
C26 C 0.30543(3) 0.59572(14) 0.60690(5) 0.02596(18) Uani 1 1 d . . . . .
H26 H 0.320723 0.693280 0.591384 0.031 Uiso 1 1 calc R U . . .
C27 C 0.27745(3) 0.49547(15) 0.56445(5) 0.0302(2) Uani 1 1 d . . . . .
H27 H 0.273499 0.525739 0.519010 0.036 Uiso 1 1 calc R U . . .
C28 C 0.25493(3) 0.35088(15) 0.58709(5) 0.0314(2) Uani 1 1 d . . . . .
H28 H 0.236271 0.284471 0.556703 0.038 Uiso 1 1 calc R U . . .
C29 C 0.25944(3) 0.30336(14) 0.65290(5) 0.02845(19) Uani 1 1 d . . . . .
H29 H 0.244126 0.205167 0.667948 0.034 Uiso 1 1 calc R U . . .
C30 C 0.28707(3) 0.40310(12) 0.69688(5) 0.02300(17) Uani 1 1 d . . . . .
C31 C 0.29716(3) 0.40080(12) 0.76750(5) 0.02278(16) Uani 1 1 d . . . . .
C32 C 0.32623(2) 0.54151(12) 0.78373(4) 0.02124(16) Uani 1 1 d . . . . .
C33 C 0.34270(3) 0.57709(13) 0.84856(4) 0.02466(17) Uani 1 1 d . . . . .
H33 H 0.363045 0.668506 0.858820 0.030 Uiso 1 1 calc R U . . .
C34 C 0.32830(3) 0.47404(14) 0.89758(5) 0.02891(19) Uani 1 1 d . . . . .
H34 H 0.338718 0.496527 0.942255 0.035 Uiso 1 1 calc R U . . .
C35 C 0.29859(3) 0.33703(14) 0.88237(5) 0.0313(2) Uani 1 1 d . . . . .
H35 H 0.288831 0.270293 0.916903 0.038 Uiso 1 1 calc R U . . .
C36 C 0.28337(3) 0.29810(13) 0.81777(5) 0.02867(19) Uani 1 1 d . . . . .
H36 H 0.263844 0.203028 0.807737 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3857(11) . ?
O1 C7 1.3940(11) . ?
N1 C6 1.3837(11) . ?
N1 C12 1.4056(11) . ?
N1 C13 1.3971(10) . ?
N2 C23 1.4231(11) . ?
N2 C25 1.3936(11) . ?
N2 C32 1.3914(11) . ?
C1 C2 1.3790(13) . ?
C1 C6 1.3805(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.4136(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3903(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.4059(11) . ?
C5 C6 1.3933(12) . ?
C5 C14 1.4516(11) . ?
C7 C8 1.3859(13) . ?
C7 C12 1.4125(11) . ?
C8 H8 0.9500 . ?
C8 C9 1.3892(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.3869(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3980(12) . ?
C11 H11 0.9500 . ?
C11 C12 1.3905(12) . ?
C13 C14 1.4242(11) . ?
C13 C18 1.3932(11) . ?
C14 C15 1.3976(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.3953(11) . ?
C16 C17 1.4078(12) . ?
C16 C19 1.4852(11) . ?
C17 H17 0.9500 . ?
C17 C18 1.3865(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.4027(11) . ?
C19 C24 1.4001(11) . ?
C20 H20 0.9500 . ?
C20 C21 1.3943(11) . ?
C21 H21 0.9500 . ?
C21 C22 1.3940(12) . ?
C22 H22 0.9500 . ?
C22 C23 1.3938(12) . ?
C23 C24 1.3942(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.3947(13) . ?
C25 C30 1.4149(12) . ?
C26 H26 0.9500 . ?
C26 C27 1.3914(13) . ?
C27 H27 0.9500 . ?
C27 C28 1.4021(16) . ?
C28 H28 0.9500 . ?
C28 C29 1.3824(15) . ?
C29 H29 0.9500 . ?
C29 C30 1.4000(12) . ?
C30 C31 1.4437(13) . ?
C31 C32 1.4136(12) . ?
C31 C36 1.3979(13) . ?
C32 C33 1.3937(12) . ?
C33 H33 0.9500 . ?
C33 C34 1.3883(13) . ?
C34 H34 0.9500 . ?
C34 C35 1.4058(15) . ?
C35 H35 0.9500 . ?
C35 C36 1.3838(15) . ?
C36 H36 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
C1 O1 C7 116.57(7) . . ?
C6 N1 C12 117.45(7) . . ?
C6 N1 C13 107.15(7) . . ?
C13 N1 C12 134.86(7) . . ?
C25 N2 C23 126.16(7) . . ?
C32 N2 C23 125.26(7) . . ?
C32 N2 C25 108.55(7) . . ?
C2 C1 O1 122.46(8) . . ?
C2 C1 C6 118.04(9) . . ?
C6 C1 O1 119.48(8) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.09(8) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 118.7 . . ?
C4 C3 C2 122.60(8) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 117.94(9) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 C14 136.92(8) . . ?
C6 C5 C4 118.19(8) . . ?
C6 C5 C14 104.89(7) . . ?
N1 C6 C5 112.04(7) . . ?
C1 C6 N1 123.84(8) . . ?
C1 C6 C5 124.12(8) . . ?
O1 C7 C12 123.59(8) . . ?
C8 C7 O1 115.74(8) . . ?
C8 C7 C12 120.67(9) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.26(9) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.79(9) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.16(9) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.77(8) . . ?
C12 C11 H11 119.6 . . ?
N1 C12 C7 117.48(8) . . ?
C11 C12 N1 124.10(7) . . ?
C11 C12 C7 118.34(8) . . ?
N1 C13 C14 108.43(7) . . ?
C18 C13 N1 130.75(8) . . ?
C18 C13 C14 120.81(7) . . ?
C13 C14 C5 107.48(7) . . ?
C15 C14 C5 132.51(8) . . ?
C15 C14 C13 120.00(7) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.66(7) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 118.85(7) . . ?
C15 C16 C19 120.52(7) . . ?
C17 C16 C19 120.63(7) . . ?
C16 C17 H17 118.5 . . ?
C18 C17 C16 122.99(7) . . ?
C18 C17 H17 118.5 . . ?
C13 C18 H18 121.2 . . ?
C17 C18 C13 117.66(8) . . ?
C17 C18 H18 121.2 . . ?
C20 C19 C16 121.83(7) . . ?
C24 C19 C16 119.74(7) . . ?
C24 C19 C20 118.43(7) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.71(8) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.57(8) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.6 . . ?
C23 C22 C21 118.85(8) . . ?
C23 C22 H22 120.6 . . ?
C22 C23 N2 119.89(7) . . ?
C22 C23 C24 120.86(8) . . ?
C24 C23 N2 119.24(7) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.49(8) . . ?
C23 C24 H24 119.8 . . ?
N2 C25 C26 129.18(8) . . ?
N2 C25 C30 108.84(8) . . ?
C26 C25 C30 121.85(8) . . ?
C25 C26 H26 121.4 . . ?
C27 C26 C25 117.11(9) . . ?
C27 C26 H26 121.4 . . ?
C26 C27 H27 119.2 . . ?
C26 C27 C28 121.63(9) . . ?
C28 C27 H27 119.2 . . ?
C27 C28 H28 119.4 . . ?
C29 C28 C27 121.10(9) . . ?
C29 C28 H28 119.4 . . ?
C28 C29 H29 120.7 . . ?
C28 C29 C30 118.54(9) . . ?
C30 C29 H29 120.7 . . ?
C25 C30 C31 106.82(7) . . ?
C29 C30 C25 119.75(9) . . ?
C29 C30 C31 133.33(9) . . ?
C32 C31 C30 106.77(8) . . ?
C36 C31 C30 133.78(8) . . ?
C36 C31 C32 119.41(9) . . ?
N2 C32 C31 109.01(8) . . ?
N2 C32 C33 129.14(8) . . ?
C33 C32 C31 121.86(8) . . ?
C32 C33 H33 121.2 . . ?
C34 C33 C32 117.56(9) . . ?
C34 C33 H33 121.2 . . ?
C33 C34 H34 119.4 . . ?
C33 C34 C35 121.24(9) . . ?
C35 C34 H34 119.4 . . ?
C34 C35 H35 119.6 . . ?
C36 C35 C34 120.88(9) . . ?
C36 C35 H35 119.6 . . ?
C31 C36 H36 120.5 . . ?
C35 C36 C31 118.98(9) . . ?
C35 C36 H36 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
O1 C1 C2 C3 177.94(8) . . . . ?
O1 C1 C6 N1 2.29(13) . . . . ?
O1 C1 C6 C5 -177.22(8) . . . . ?
O1 C7 C8 C9 179.42(8) . . . . ?
O1 C7 C12 N1 -1.88(12) . . . . ?
O1 C7 C12 C11 -178.84(8) . . . . ?
N1 C13 C14 C5 -1.23(9) . . . . ?
N1 C13 C14 C15 177.76(7) . . . . ?
N1 C13 C18 C17 -178.93(8) . . . . ?
N2 C23 C24 C19 -178.42(7) . . . . ?
N2 C25 C26 C27 -176.20(9) . . . . ?
N2 C25 C30 C29 177.71(8) . . . . ?
N2 C25 C30 C31 0.90(9) . . . . ?
N2 C32 C33 C34 177.08(9) . . . . ?
C1 O1 C7 C8 -167.18(8) . . . . ?
C1 O1 C7 C12 11.90(12) . . . . ?
C1 C2 C3 C4 -0.37(14) . . . . ?
C2 C1 C6 N1 -179.34(8) . . . . ?
C2 C1 C6 C5 1.15(13) . . . . ?
C2 C3 C4 C5 0.39(13) . . . . ?
C3 C4 C5 C6 0.32(12) . . . . ?
C3 C4 C5 C14 -179.13(9) . . . . ?
C4 C5 C6 N1 179.31(7) . . . . ?
C4 C5 C6 C1 -1.12(13) . . . . ?
C4 C5 C14 C13 -179.12(10) . . . . ?
C4 C5 C14 C15 2.07(17) . . . . ?
C5 C14 C15 C16 179.96(8) . . . . ?
C6 N1 C12 C7 -7.96(11) . . . . ?
C6 N1 C12 C11 168.81(8) . . . . ?
C6 N1 C13 C14 0.58(9) . . . . ?
C6 N1 C13 C18 179.38(9) . . . . ?
C6 C1 C2 C3 -0.38(13) . . . . ?
C6 C5 C14 C13 1.38(9) . . . . ?
C6 C5 C14 C15 -177.43(9) . . . . ?
C7 O1 C1 C2 169.83(8) . . . . ?
C7 O1 C1 C6 -11.87(11) . . . . ?
C7 C8 C9 C10 -0.27(15) . . . . ?
C8 C7 C12 N1 177.16(8) . . . . ?
C8 C7 C12 C11 0.20(13) . . . . ?
C8 C9 C10 C11 -0.26(15) . . . . ?
C9 C10 C11 C12 0.78(15) . . . . ?
C10 C11 C12 N1 -177.48(8) . . . . ?
C10 C11 C12 C7 -0.74(13) . . . . ?
C12 N1 C6 C1 8.01(12) . . . . ?
C12 N1 C6 C5 -172.43(7) . . . . ?
C12 N1 C13 C14 171.50(8) . . . . ?
C12 N1 C13 C18 -9.69(16) . . . . ?
C12 C7 C8 C9 0.31(14) . . . . ?
C13 N1 C6 C1 -179.23(8) . . . . ?
C13 N1 C6 C5 0.34(9) . . . . ?
C13 N1 C12 C7 -178.18(8) . . . . ?
C13 N1 C12 C11 -1.41(15) . . . . ?
C13 C14 C15 C16 1.27(12) . . . . ?
C14 C5 C6 N1 -1.08(9) . . . . ?
C14 C5 C6 C1 178.49(8) . . . . ?
C14 C13 C18 C17 -0.25(12) . . . . ?
C14 C15 C16 C17 0.05(12) . . . . ?
C14 C15 C16 C19 -179.54(7) . . . . ?
C15 C16 C17 C18 -1.57(13) . . . . ?
C15 C16 C19 C20 -139.59(8) . . . . ?
C15 C16 C19 C24 40.62(11) . . . . ?
C16 C17 C18 C13 1.64(13) . . . . ?
C16 C19 C20 C21 177.14(8) . . . . ?
C16 C19 C24 C23 -177.79(7) . . . . ?
C17 C16 C19 C20 40.82(12) . . . . ?
C17 C16 C19 C24 -138.97(8) . . . . ?
C18 C13 C14 C5 179.82(7) . . . . ?
C18 C13 C14 C15 -1.19(12) . . . . ?
C19 C16 C17 C18 178.03(8) . . . . ?
C19 C20 C21 C22 1.06(13) . . . . ?
C20 C19 C24 C23 2.41(12) . . . . ?
C20 C21 C22 C23 1.64(13) . . . . ?
C21 C22 C23 N2 176.37(8) . . . . ?
C21 C22 C23 C24 -2.29(13) . . . . ?
C22 C23 C24 C19 0.25(13) . . . . ?
C23 N2 C25 C26 -6.83(14) . . . . ?
C23 N2 C25 C30 177.25(8) . . . . ?
C23 N2 C32 C31 -177.75(8) . . . . ?
C23 N2 C32 C33 2.49(14) . . . . ?
C24 C19 C20 C21 -3.07(12) . . . . ?
C25 N2 C23 C22 126.95(9) . . . . ?
C25 N2 C23 C24 -54.36(12) . . . . ?
C25 N2 C32 C31 0.25(10) . . . . ?
C25 N2 C32 C33 -179.51(9) . . . . ?
C25 C26 C27 C28 -0.27(14) . . . . ?
C25 C30 C31 C32 -0.74(9) . . . . ?
C25 C30 C31 C36 176.65(10) . . . . ?
C26 C25 C30 C29 1.43(13) . . . . ?
C26 C25 C30 C31 -175.37(8) . . . . ?
C26 C27 C28 C29 0.61(15) . . . . ?
C27 C28 C29 C30 0.07(14) . . . . ?
C28 C29 C30 C25 -1.06(13) . . . . ?
C28 C29 C30 C31 174.74(9) . . . . ?
C29 C30 C31 C32 -176.92(9) . . . . ?
C29 C30 C31 C36 0.47(18) . . . . ?
C30 C25 C26 C27 -0.74(13) . . . . ?
C30 C31 C32 N2 0.31(10) . . . . ?
C30 C31 C32 C33 -179.91(8) . . . . ?
C30 C31 C36 C35 -177.13(10) . . . . ?
C31 C32 C33 C34 -2.65(13) . . . . ?
C32 N2 C23 C22 -55.39(12) . . . . ?
C32 N2 C23 C24 123.29(9) . . . . ?
C32 N2 C25 C26 175.20(9) . . . . ?
C32 N2 C25 C30 -0.72(9) . . . . ?
C32 C31 C36 C35 0.00(14) . . . . ?
C32 C33 C34 C35 0.86(14) . . . . ?
C33 C34 C35 C36 1.34(15) . . . . ?
C34 C35 C36 C31 -1.75(15) . . . . ?
C36 C31 C32 N2 -177.53(8) . . . . ?
C36 C31 C32 C33 2.26(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
