# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_hd_wql26
_database_code_depnum_ccdc_archive 'CCDC 1978767'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2020-01-19 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C27 H28 N2 O3'
_chemical_formula_sum            'C27 H28 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         428.51

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   11.0515(3)
_cell_length_b                   21.2790(6)
_cell_length_c                   9.5549(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.6080(10)
_cell_angle_gamma                90
_cell_volume                     2208.58(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      4.0697
_cell_measurement_theta_max      72.3744
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912

_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            22635
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_theta_min         4.07
_diffrn_reflns_theta_max         72.37
_diffrn_reflns_theta_full        72.37
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             4355
_reflns_number_gt                4060
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1025
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_number_reflns         4355
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.8860P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.45308(7) 0.45949(4) 0.13595(8) 0.01826(19) Uani d . . . 1 . .
O O2 0.52378(9) 0.52188(5) 0.32303(10) 0.0304(2) Uani d . . . 1 . .
O O3 0.08672(10) 0.56090(5) 0.83690(10) 0.0297(2) Uani d . . . 1 . .
N N1 0.20243(9) 0.44343(5) 0.47709(10) 0.0163(2) Uani d . . . 1 . .
N N2 0.27832(9) 0.54009(5) 0.36201(10) 0.0170(2) Uani d . . . 1 . .
C C1 0.38382(14) 0.24057(7) 0.17926(16) 0.0296(3) Uani d . . . 1 . .
H H11 0.468567 0.249832 0.168834 0.044 Uiso calc U . R 1 . .
H H12 0.331865 0.236453 0.084848 0.044 Uiso calc U . R 1 . .
H H1 0.382128 0.201167 0.231975 0.044 Uiso calc U . R 1 . .
C C2 0.33598(12) 0.29323(6) 0.25942(13) 0.0206(3) Uani d . . . 1 . .
C C3 0.41668(11) 0.33251(6) 0.34903(12) 0.0199(3) Uani d . . . 1 . .
H H13 0.502867 0.325653 0.360301 0.024 Uiso calc U . R 1 . .
C C4 0.37301(11) 0.38154(6) 0.42211(12) 0.0188(2) Uani d . . . 1 . .
H H8 0.428752 0.40783 0.483394 0.023 Uiso calc U . R 1 . .
C C5 0.24700(11) 0.39163(5) 0.40449(11) 0.0162(2) Uani d . . . 1 . .
C C6 0.22671(10) 0.50601(6) 0.45882(12) 0.0159(2) Uani d . . . 1 . .
C C7 0.30548(11) 0.51725(6) 0.22859(12) 0.0167(2) Uani d . . . 1 . .
H H7 0.282526 0.549883 0.154611 0.02 Uiso calc U . R 1 . .
H H6 0.254657 0.479577 0.19885 0.02 Uiso calc U . R 1 . .
C C8 0.44053(11) 0.50052(6) 0.23801(12) 0.0171(2) Uani d . . . 1 . .
C C9 0.57844(11) 0.43793(6) 0.13633(13) 0.0208(3) Uani d . . . 1 . .
H H28 0.617726 0.42435 0.233154 0.025 Uiso calc U . R 1 . .
H H5 0.628279 0.472232 0.105828 0.025 Uiso calc U . R 1 . .
C C10 0.56979(12) 0.38360(6) 0.03399(14) 0.0238(3) Uani d . . . 1 . .
H H3 0.521731 0.349665 0.066467 0.036 Uiso calc U . R 1 . .
H H4 0.652695 0.368296 0.029832 0.036 Uiso calc U . R 1 . .
H H2 0.529322 0.397464 -0.060937 0.036 Uiso calc U . R 1 . .
C C11 0.27272(11) 0.60295(6) 0.40352(12) 0.0166(2) Uani d . . . 1 . .
C C12 0.21716(10) 0.60646(6) 0.52728(12) 0.0160(2) Uani d . . . 1 . .
C C13 0.18860(10) 0.54294(6) 0.55993(12) 0.0160(2) Uani d . . . 1 . .
C C14 0.13704(10) 0.50006(6) 0.64943(12) 0.0158(2) Uani d . . . 1 . .
C C15 0.14687(10) 0.44018(6) 0.59615(12) 0.0161(2) Uani d . . . 1 . .
C C16 0.20993(12) 0.30424(6) 0.24453(13) 0.0214(3) Uani d . . . 1 . .
H H9 0.153952 0.277678 0.184268 0.026 Uiso calc U . R 1 . .
C C17 0.16430(11) 0.35323(6) 0.31596(12) 0.0194(3) Uani d . . . 1 . .
H H10 0.078177 0.360345 0.304489 0.023 Uiso calc U . R 1 . .
C C18 0.10541(11) 0.38062(6) 0.65434(12) 0.0171(2) Uani d . . . 1 . .
H H14 0.164069 0.3465 0.644164 0.021 Uiso calc U . R 1 . .
H H15 0.023607 0.368691 0.599776 0.021 Uiso calc U . R 1 . .
C C19 0.09760(11) 0.38887(6) 0.81341(12) 0.0178(2) Uani d . . . 1 . .
C C20 0.03182(12) 0.45134(6) 0.83279(13) 0.0211(3) Uani d . . . 1 . .
H H17 -0.055029 0.447766 0.783924 0.025 Uiso calc U . R 1 . .
H H16 0.031722 0.45722 0.935549 0.025 Uiso calc U . R 1 . .
C C21 0.08681(11) 0.50960(6) 0.77768(12) 0.0195(3) Uani d . . . 1 . .
C C22 0.22728(12) 0.38902(6) 0.90390(13) 0.0223(3) Uani d . . . 1 . .
H H20 0.222221 0.397768 1.003357 0.033 Uiso calc U . R 1 . .
H H18 0.27697 0.421532 0.868805 0.033 Uiso calc U . R 1 . .
H H19 0.265638 0.347856 0.897446 0.033 Uiso calc U . R 1 . .
C C23 0.02330(12) 0.33484(6) 0.86136(13) 0.0232(3) Uani d . . . 1 . .
H H23 0.067326 0.295172 0.85623 0.035 Uiso calc U . R 1 . .
H H21 -0.057558 0.332611 0.79893 0.035 Uiso calc U . R 1 . .
H H22 0.012593 0.342157 0.959606 0.035 Uiso calc U . R 1 . .
C C24 0.20037(11) 0.66559(6) 0.58505(12) 0.0190(2) Uani d . . . 1 . .
H H27 0.165274 0.669128 0.668311 0.023 Uiso calc U . R 1 . .
C C25 0.23554(12) 0.71897(6) 0.51938(13) 0.0215(3) Uani d . . . 1 . .
H H26 0.222886 0.759214 0.557269 0.026 Uiso calc U . R 1 . .
C C26 0.28948(11) 0.71442(6) 0.39789(13) 0.0214(3) Uani d . . . 1 . .
H H25 0.312713 0.751669 0.354794 0.026 Uiso calc U . R 1 . .
C C27 0.30957(11) 0.65638(6) 0.33941(12) 0.0195(3) Uani d . . . 1 . .
H H24 0.347365 0.653388 0.258049 0.023 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . 1.3350(14) ?
O1 C9 . 1.4587(14) ?
O2 C8 . 1.1991(15) ?
O3 C21 . 1.2295(16) ?
N1 C6 . 1.3758(16) ?
N1 C15 . 1.3903(15) ?
N1 C5 . 1.4369(15) ?
N2 C6 . 1.3788(15) ?
N2 C11 . 1.3998(15) ?
N2 C7 . 1.4465(14) ?
C1 C2 . 1.5070(17) ?
C1 H11 . 0.98 ?
C1 H12 . 0.98 ?
C1 H1 . 0.98 ?
C2 C16 . 1.3938(18) ?
C2 C3 . 1.3950(18) ?
C3 C4 . 1.3902(17) ?
C3 H13 . 0.95 ?
C4 C5 . 1.3884(17) ?
C4 H8 . 0.95 ?
C5 C17 . 1.3905(17) ?
C6 C13 . 1.3705(16) ?
C7 C8 . 1.5209(16) ?
C7 H7 . 0.99 ?
C7 H6 . 0.99 ?
C9 C10 . 1.5060(18) ?
C9 H28 . 0.99 ?
C9 H5 . 0.99 ?
C10 H3 . 0.98 ?
C10 H4 . 0.98 ?
C10 H2 . 0.98 ?
C11 C27 . 1.3876(17) ?
C11 C12 . 1.4312(16) ?
C12 C24 . 1.4001(17) ?
C12 C13 . 1.4353(17) ?
C13 C14 . 1.4381(16) ?
C14 C15 . 1.3838(17) ?
C14 C21 . 1.4497(16) ?
C15 C18 . 1.4896(16) ?
C16 C17 . 1.3906(17) ?
C16 H9 . 0.95 ?
C17 H10 . 0.95 ?
C18 C19 . 1.5481(15) ?
C18 H14 . 0.99 ?
C18 H15 . 0.99 ?
C19 C23 . 1.5312(17) ?
C19 C22 . 1.5315(17) ?
C19 C20 . 1.5424(17) ?
C20 C21 . 1.5170(18) ?
C20 H17 . 0.99 ?
C20 H16 . 0.99 ?
C22 H20 . 0.98 ?
C22 H18 . 0.98 ?
C22 H19 . 0.98 ?
C23 H23 . 0.98 ?
C23 H21 . 0.98 ?
C23 H22 . 0.98 ?
C24 C25 . 1.3874(18) ?
C24 H27 . 0.95 ?
C25 C26 . 1.4025(18) ?
C25 H26 . 0.95 ?
C26 C27 . 1.3901(18) ?
C26 H25 . 0.95 ?
C27 H24 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O1 C9 . . 115.48(9) ?
C6 N1 C15 . . 106.13(9) ?
C6 N1 C5 . . 126.09(9) ?
C15 N1 C5 . . 126.81(10) ?
C6 N2 C11 . . 105.50(9) ?
C6 N2 C7 . . 126.39(10) ?
C11 N2 C7 . . 126.72(10) ?
C2 C1 H11 . . 109.5 ?
C2 C1 H12 . . 109.5 ?
H11 C1 H12 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H11 C1 H1 . . 109.5 ?
H12 C1 H1 . . 109.5 ?
C16 C2 C3 . . 118.42(11) ?
C16 C2 C1 . . 120.71(12) ?
C3 C2 C1 . . 120.87(12) ?
C4 C3 C2 . . 121.07(11) ?
C4 C3 H13 . . 119.5 ?
C2 C3 H13 . . 119.5 ?
C5 C4 C3 . . 119.23(11) ?
C5 C4 H8 . . 120.4 ?
C3 C4 H8 . . 120.4 ?
C4 C5 C17 . . 121.01(11) ?
C4 C5 N1 . . 119.04(10) ?
C17 C5 N1 . . 119.94(11) ?
C13 C6 N1 . . 111.91(10) ?
C13 C6 N2 . . 112.96(11) ?
N1 C6 N2 . . 135.12(10) ?
N2 C7 C8 . . 112.77(9) ?
N2 C7 H7 . . 109.0 ?
C8 C7 H7 . . 109.0 ?
N2 C7 H6 . . 109.0 ?
C8 C7 H6 . . 109.0 ?
H7 C7 H6 . . 107.8 ?
O2 C8 O1 . . 124.95(11) ?
O2 C8 C7 . . 125.00(11) ?
O1 C8 C7 . . 110.04(10) ?
O1 C9 C10 . . 107.05(10) ?
O1 C9 H28 . . 110.3 ?
C10 C9 H28 . . 110.3 ?
O1 C9 H5 . . 110.3 ?
C10 C9 H5 . . 110.3 ?
H28 C9 H5 . . 108.6 ?
C9 C10 H3 . . 109.5 ?
C9 C10 H4 . . 109.5 ?
H3 C10 H4 . . 109.5 ?
C9 C10 H2 . . 109.5 ?
H3 C10 H2 . . 109.5 ?
H4 C10 H2 . . 109.5 ?
C27 C11 N2 . . 128.76(11) ?
C27 C11 C12 . . 121.83(11) ?
N2 C11 C12 . . 109.39(10) ?
C24 C12 C11 . . 118.75(11) ?
C24 C12 C13 . . 135.25(11) ?
C11 C12 C13 . . 105.99(10) ?
C6 C13 C12 . . 106.16(10) ?
C6 C13 C14 . . 105.20(11) ?
C12 C13 C14 . . 148.64(11) ?
C15 C14 C13 . . 107.40(10) ?
C15 C14 C21 . . 120.54(11) ?
C13 C14 C21 . . 132.00(11) ?
C14 C15 N1 . . 109.37(10) ?
C14 C15 C18 . . 126.56(10) ?
N1 C15 C18 . . 124.07(10) ?
C17 C16 C2 . . 121.45(12) ?
C17 C16 H9 . . 119.3 ?
C2 C16 H9 . . 119.3 ?
C5 C17 C16 . . 118.82(11) ?
C5 C17 H10 . . 120.6 ?
C16 C17 H10 . . 120.6 ?
C15 C18 C19 . . 110.28(10) ?
C15 C18 H14 . . 109.6 ?
C19 C18 H14 . . 109.6 ?
C15 C18 H15 . . 109.6 ?
C19 C18 H15 . . 109.6 ?
H14 C18 H15 . . 108.1 ?
C23 C19 C22 . . 109.28(10) ?
C23 C19 C20 . . 108.70(10) ?
C22 C19 C20 . . 110.07(10) ?
C23 C19 C18 . . 109.79(10) ?
C22 C19 C18 . . 109.81(10) ?
C20 C19 C18 . . 109.17(10) ?
C21 C20 C19 . . 115.78(10) ?
C21 C20 H17 . . 108.3 ?
C19 C20 H17 . . 108.3 ?
C21 C20 H16 . . 108.3 ?
C19 C20 H16 . . 108.3 ?
H17 C20 H16 . . 107.4 ?
O3 C21 C14 . . 123.11(12) ?
O3 C21 C20 . . 122.11(11) ?
C14 C21 C20 . . 114.78(11) ?
C19 C22 H20 . . 109.5 ?
C19 C22 H18 . . 109.5 ?
H20 C22 H18 . . 109.5 ?
C19 C22 H19 . . 109.5 ?
H20 C22 H19 . . 109.5 ?
H18 C22 H19 . . 109.5 ?
C19 C23 H23 . . 109.5 ?
C19 C23 H21 . . 109.5 ?
H23 C23 H21 . . 109.5 ?
C19 C23 H22 . . 109.5 ?
H23 C23 H22 . . 109.5 ?
H21 C23 H22 . . 109.5 ?
C25 C24 C12 . . 119.27(11) ?
C25 C24 H27 . . 120.4 ?
C12 C24 H27 . . 120.4 ?
C24 C25 C26 . . 121.00(11) ?
C24 C25 H26 . . 119.5 ?
C26 C25 H26 . . 119.5 ?
C27 C26 C25 . . 121.17(12) ?
C27 C26 H25 . . 119.4 ?
C25 C26 H25 . . 119.4 ?
C11 C27 C26 . . 117.97(11) ?
C11 C27 H24 . . 121.0 ?
C26 C27 H24 . . 121.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C16 C2 C3 C4 . . . . 0.03(18) ?
C1 C2 C3 C4 . . . . 179.37(11) ?
C2 C3 C4 C5 . . . . -0.44(18) ?
C3 C4 C5 C17 . . . . 0.49(17) ?
C3 C4 C5 N1 . . . . -178.27(10) ?
C6 N1 C5 C4 . . . . 61.64(15) ?
C15 N1 C5 C4 . . . . -105.45(14) ?
C6 N1 C5 C17 . . . . -117.12(13) ?
C15 N1 C5 C17 . . . . 75.78(15) ?
C15 N1 C6 C13 . . . . -0.40(13) ?
C5 N1 C6 C13 . . . . -169.67(10) ?
C15 N1 C6 N2 . . . . -179.19(13) ?
C5 N1 C6 N2 . . . . 11.5(2) ?
C11 N2 C6 C13 . . . . -0.13(13) ?
C7 N2 C6 C13 . . . . -167.28(11) ?
C11 N2 C6 N1 . . . . 178.65(13) ?
C7 N2 C6 N1 . . . . 11.5(2) ?
C6 N2 C7 C8 . . . . -100.10(13) ?
C11 N2 C7 C8 . . . . 95.41(14) ?
C9 O1 C8 O2 . . . . 3.20(18) ?
C9 O1 C8 C7 . . . . -178.03(9) ?
N2 C7 C8 O2 . . . . -24.26(17) ?
N2 C7 C8 O1 . . . . 156.97(10) ?
C8 O1 C9 C10 . . . . 169.14(10) ?
C6 N2 C11 C27 . . . . -178.16(12) ?
C7 N2 C11 C27 . . . . -11.1(2) ?
C6 N2 C11 C12 . . . . 0.15(13) ?
C7 N2 C11 C12 . . . . 167.24(11) ?
C27 C11 C12 C24 . . . . -0.31(17) ?
N2 C11 C12 C24 . . . . -178.75(10) ?
C27 C11 C12 C13 . . . . 178.33(11) ?
N2 C11 C12 C13 . . . . -0.11(13) ?
N1 C6 C13 C12 . . . . -179.01(9) ?
N2 C6 C13 C12 . . . . 0.06(13) ?
N1 C6 C13 C14 . . . . 0.42(13) ?
N2 C6 C13 C14 . . . . 179.50(10) ?
C24 C12 C13 C6 . . . . 178.33(13) ?
C11 C12 C13 C6 . . . . 0.03(13) ?
C24 C12 C13 C14 . . . . -0.6(3) ?
C11 C12 C13 C14 . . . . -178.92(18) ?
C6 C13 C14 C15 . . . . -0.28(13) ?
C12 C13 C14 C15 . . . . 178.67(18) ?
C6 C13 C14 C21 . . . . 176.74(12) ?
C12 C13 C14 C21 . . . . -4.3(3) ?
C13 C14 C15 N1 . . . . 0.05(13) ?
C21 C14 C15 N1 . . . . -177.38(10) ?
C13 C14 C15 C18 . . . . -179.92(11) ?
C21 C14 C15 C18 . . . . 2.65(18) ?
C6 N1 C15 C14 . . . . 0.20(13) ?
C5 N1 C15 C14 . . . . 169.38(10) ?
C6 N1 C15 C18 . . . . -179.83(10) ?
C5 N1 C15 C18 . . . . -10.66(18) ?
C3 C2 C16 C17 . . . . 0.37(18) ?
C1 C2 C16 C17 . . . . -178.98(12) ?
C4 C5 C17 C16 . . . . -0.11(17) ?
N1 C5 C17 C16 . . . . 178.63(10) ?
C2 C16 C17 C5 . . . . -0.33(18) ?
C14 C15 C18 C19 . . . . -22.83(16) ?
N1 C15 C18 C19 . . . . 157.21(11) ?
C15 C18 C19 C23 . . . . 164.84(10) ?
C15 C18 C19 C22 . . . . -74.99(12) ?
C15 C18 C19 C20 . . . . 45.77(13) ?
C23 C19 C20 C21 . . . . -174.63(10) ?
C22 C19 C20 C21 . . . . 65.71(13) ?
C18 C19 C20 C21 . . . . -54.89(14) ?
C15 C14 C21 O3 . . . . 172.92(12) ?
C13 C14 C21 O3 . . . . -3.8(2) ?
C15 C14 C21 C20 . . . . -8.06(16) ?
C13 C14 C21 C20 . . . . 175.24(12) ?
C19 C20 C21 O3 . . . . -145.61(12) ?
C19 C20 C21 C14 . . . . 35.36(15) ?
C11 C12 C24 C25 . . . . 1.31(17) ?
C13 C12 C24 C25 . . . . -176.83(13) ?
C12 C24 C25 C26 . . . . -1.15(18) ?
C24 C25 C26 C27 . . . . -0.05(19) ?
N2 C11 C27 C26 . . . . 177.25(12) ?
C12 C11 C27 C26 . . . . -0.87(18) ?
C25 C26 C27 C11 . . . . 1.05(18) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H8 O2 3_666 0.95 2.36 3.2298(15) 151.8 ?
C17 H10 O3 3_566 0.95 2.65 3.4171(16) 137.6 ?
C20 H17 N2 3_566 0.99 2.61 3.5913(17) 169.1 ?



####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2168123'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N2 O'
_chemical_formula_sum            'C23 H20 N2 O'
_chemical_formula_weight         340.41
_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      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                   9.674(3)
_cell_length_b                   9.935(3)
_cell_length_c                   10.704(3)
_cell_angle_alpha                87.411(11)
_cell_angle_beta                 65.196(11)
_cell_angle_gamma                76.494(12)
_cell_volume                     906.5(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3936
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1426 before and 0.0904 after correction. The Ratio of minimum to maximum transmission is 0.6980. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11940
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_min         2.387
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2493
_reflns_number_total             3682
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3682
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0814
_refine_ls_restrained_S_all      1.109
_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)+(0.1541P)²+0.1537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2359
_refine_ls_wR_factor_ref         0.2680
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C23A-O1A
 1.45 with sigma of 0.02
 C23-O1
 1.65 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(O1) = Uanis(O1A)
4. Others
 Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(O1A)=
 Sof(H1AA)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(O1)=Sof(H1A)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C22A(H22C,H22D), C23A(H23C,H23D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O1A(H1AA)
;
_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
C1 C 0.1403(3) 1.3934(3) 0.3288(3) 0.0726(7) Uani 1 1 d . . . . .
H1 H 0.1440 1.4512 0.3927 0.087 Uiso 1 1 calc R . . . .
C2 C 0.0998(4) 1.4479(3) 0.2245(3) 0.0892(9) Uani 1 1 d . . . . .
H2 H 0.0765 1.5435 0.2183 0.107 Uiso 1 1 calc R . . . .
C3 C 0.0932(4) 1.3631(3) 0.1289(3) 0.0901(9) Uani 1 1 d . . . . .
H3 H 0.0648 1.4033 0.0604 0.108 Uiso 1 1 calc R . . . .
C4 C 0.1275(3) 1.2219(3) 0.1328(3) 0.0761(8) Uani 1 1 d . . . . .
H4 H 0.1244 1.1655 0.0673 0.091 Uiso 1 1 calc R . . . .
C5 C 0.1668(3) 1.1657(3) 0.2376(2) 0.0624(6) Uani 1 1 d . . . . .
C6 C 0.1756(3) 1.2495(2) 0.3362(2) 0.0588(6) Uani 1 1 d . . . . .
C7 C 0.2191(3) 1.1550(2) 0.4262(2) 0.0590(6) Uani 1 1 d . . . . .
C8 C 0.2343(3) 1.0250(3) 0.3788(2) 0.0681(7) Uani 1 1 d . . . . .
C9 C 0.2774(3) 0.9957(3) 0.5656(3) 0.0744(7) Uani 1 1 d . . . . .
C10 C 0.2466(3) 1.1403(2) 0.5485(2) 0.0587(6) Uani 1 1 d . . . . .
C11 C 0.2471(3) 1.2298(3) 0.6440(2) 0.0648(6) Uani 1 1 d . . . . .
H11 H 0.2263 1.3251 0.6352 0.078 Uiso 1 1 calc R . . . .
C12 C 0.2791(3) 1.1747(3) 0.7531(3) 0.0753(7) Uani 1 1 d . . . . .
H12 H 0.2805 1.2340 0.8171 0.090 Uiso 1 1 calc R . . . .
C13 C 0.3090(4) 1.0340(3) 0.7685(3) 0.0858(9) Uani 1 1 d . . . . .
H13 H 0.3299 1.0001 0.8427 0.103 Uiso 1 1 calc R . . . .
C14 C 0.3083(4) 0.9421(3) 0.6754(3) 0.0914(9) Uani 1 1 d . . . . .
H14 H 0.3281 0.8471 0.6863 0.110 Uiso 1 1 calc R . . . .
C15 C 0.2459(3) 0.9128(2) 0.1655(2) 0.0616(6) Uani 1 1 d . . . . .
C16 C 0.4014(3) 0.8498(3) 0.0907(3) 0.0772(7) Uani 1 1 d . . . . .
H16 H 0.4779 0.8780 0.1068 0.093 Uiso 1 1 calc R . . . .
C17 C 0.4444(3) 0.7448(3) -0.0083(3) 0.0811(8) Uani 1 1 d . . . . .
H17 H 0.5499 0.7021 -0.0572 0.097 Uiso 1 1 calc R . . . .
C18 C 0.3337(4) 0.7025(3) -0.0355(3) 0.0740(7) Uani 1 1 d . . . . .
C19 C 0.1793(4) 0.7682(3) 0.0392(3) 0.0779(8) Uani 1 1 d . . . . .
H19 H 0.1027 0.7416 0.0219 0.094 Uiso 1 1 calc R . . . .
C20 C 0.1342(3) 0.8725(3) 0.1391(3) 0.0708(7) Uani 1 1 d . . . . .
H20 H 0.0287 0.9152 0.1881 0.085 Uiso 1 1 calc R . . . .
C21 C 0.3819(6) 0.5881(4) -0.1439(4) 0.1180(13) Uani 1 1 d . . . . .
H21A H 0.3668 0.5029 -0.1002 0.177 Uiso 1 1 calc GR . . . .
H21B H 0.4904 0.5775 -0.2054 0.177 Uiso 1 1 calc GR . . . .
H21C H 0.3191 0.6110 -0.1949 0.177 Uiso 1 1 calc GR . . . .
N1 N 0.2008(3) 1.0255(2) 0.2650(2) 0.0738(6) Uani 1 1 d . . . . .
N2 N 0.2686(3) 0.9242(2) 0.4597(2) 0.0873(8) Uani 1 1 d . . . . .
C22 C 0.2198(5) 0.7867(4) 0.4758(4) 0.0639(8) Uani 0.611(3) 1 d . . P A 1
H22A H 0.1604 0.7741 0.5726 0.077 Uiso 0.611(3) 1 calc R . P A 1
H22B H 0.1544 0.7862 0.4278 0.077 Uiso 0.611(3) 1 calc R . P A 1
C23 C 0.3631(7) 0.6736(6) 0.4172(6) 0.0975(14) Uani 0.611(3) 1 d D . P A 1
H23A H 0.3333 0.5888 0.4093 0.117 Uiso 0.611(3) 1 calc R . P A 1
H23B H 0.4281 0.6954 0.3249 0.117 Uiso 0.611(3) 1 calc R . P A 1
O1 O 0.4469(7) 0.6513(6) 0.4892(7) 0.1527(17) Uani 0.611(3) 1 d D . P A 1
H1A H 0.4447 0.5751 0.5217 0.229 Uiso 0.611(3) 1 calc GR . P A 1
C22A C 0.3547(8) 0.7779(7) 0.4206(7) 0.0639(8) Uani 0.389(3) 1 d . . P A 2
H22C H 0.4411 0.7538 0.4476 0.077 Uiso 0.389(3) 1 calc R . P A 2
H22D H 0.3935 0.7564 0.3225 0.077 Uiso 0.389(3) 1 calc R . P A 2
C23A C 0.2277(12) 0.7093(9) 0.5027(11) 0.0975(14) Uani 0.389(3) 1 d D . P A 2
H23C H 0.1507 0.7219 0.4647 0.117 Uiso 0.389(3) 1 calc R . P A 2
H23D H 0.1757 0.7463 0.5977 0.117 Uiso 0.389(3) 1 calc R . P A 2
O1A O 0.3074(11) 0.5599(8) 0.4934(12) 0.1527(17) Uani 0.389(3) 1 d D . P A 2
H1AA H 0.4027 0.5511 0.4580 0.229 Uiso 0.389(3) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.381(4) . ?
C1 C6 1.397(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 C6 1.415(3) . ?
C5 N1 1.402(3) . ?
C6 C7 1.435(3) . ?
C7 C8 1.362(4) . ?
C7 C10 1.437(3) . ?
C8 N1 1.385(3) . ?
C8 N2 1.368(3) . ?
C9 C10 1.418(4) . ?
C9 C14 1.385(4) . ?
C9 N2 1.406(3) . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C15 C20 1.370(3) . ?
C15 N1 1.439(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(4) . ?
C18 C19 1.374(4) . ?
C18 C21 1.507(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N2 C22 1.526(5) . ?
N2 C22A 1.476(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.478(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 O1 1.313(7) . ?
O1 H1A 0.8200 . ?
C22A H22C 0.9700 . ?
C22A H22D 0.9700 . ?
C22A C23A 1.476(11) . ?
C23A H23C 0.9700 . ?
C23A H23D 0.9700 . ?
C23A O1A 1.491(11) . ?
O1A H1AA 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.7 . . ?
C2 C1 C6 118.5(3) . . ?
C6 C1 H1 120.7 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.6(3) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 122.1(2) . . ?
C4 C5 N1 127.8(2) . . ?
N1 C5 C6 110.15(19) . . ?
C1 C6 C5 118.7(2) . . ?
C1 C6 C7 135.6(2) . . ?
C5 C6 C7 105.7(2) . . ?
C6 C7 C10 146.3(2) . . ?
C8 C7 C6 106.7(2) . . ?
C8 C7 C10 107.0(2) . . ?
C7 C8 N1 112.7(2) . . ?
C7 C8 N2 112.9(2) . . ?
N2 C8 N1 134.3(2) . . ?
C14 C9 C10 121.3(2) . . ?
C14 C9 N2 128.5(3) . . ?
N2 C9 C10 110.2(2) . . ?
C9 C10 C7 105.0(2) . . ?
C11 C10 C7 135.8(2) . . ?
C11 C10 C9 119.2(2) . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.9(2) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 H14 121.0 . . ?
C13 C14 C9 118.1(3) . . ?
C13 C14 H14 121.0 . . ?
C16 C15 N1 120.5(2) . . ?
C20 C15 C16 119.4(2) . . ?
C20 C15 N1 120.0(2) . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.3(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C21 120.6(3) . . ?
C19 C18 C17 117.6(2) . . ?
C19 C18 C21 121.8(3) . . ?
C18 C19 H19 118.9 . . ?
C18 C19 C20 122.1(2) . . ?
C20 C19 H19 118.9 . . ?
C15 C20 C19 119.5(3) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 N1 C15 123.80(18) . . ?
C8 N1 C5 104.83(19) . . ?
C8 N1 C15 127.7(2) . . ?
C8 N2 C9 105.0(2) . . ?
C8 N2 C22 123.6(3) . . ?
C8 N2 C22A 128.9(3) . . ?
C9 N2 C22 124.1(2) . . ?
C9 N2 C22A 119.9(3) . . ?
N2 C22 H22A 110.0 . . ?
N2 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
C23 C22 N2 108.3(4) . . ?
C23 C22 H22A 110.0 . . ?
C23 C22 H22B 110.0 . . ?
C22 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
O1 C23 C22 114.6(6) . . ?
O1 C23 H23A 108.6 . . ?
O1 C23 H23B 108.6 . . ?
C23 O1 H1A 109.5 . . ?
N2 C22A H22C 111.9 . . ?
N2 C22A H22D 111.9 . . ?
N2 C22A C23A 99.6(6) . . ?
H22C C22A H22D 109.6 . . ?
C23A C22A H22C 111.9 . . ?
C23A C22A H22D 111.9 . . ?
C22A C23A H23C 110.8 . . ?
C22A C23A H23D 110.8 . . ?
C22A C23A O1A 104.7(7) . . ?
H23C C23A H23D 108.9 . . ?
O1A C23A H23C 110.8 . . ?
O1A C23A H23D 110.8 . . ?
C23A O1A H1AA 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O1 0.82 2.23 2.973(11) 150.1 2_666

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.5(5) . . . . ?
C1 C6 C7 C8 178.7(3) . . . . ?
C1 C6 C7 C10 3.1(5) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C1 C6 C7 -179.0(3) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C3 C4 C5 N1 177.6(3) . . . . ?
C4 C5 C6 C1 1.3(4) . . . . ?
C4 C5 C6 C7 -179.9(2) . . . . ?
C4 C5 N1 C8 179.3(3) . . . . ?
C4 C5 N1 C15 19.3(4) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C5 C6 C7 C10 -175.4(3) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C6 C5 N1 C8 -1.5(3) . . . . ?
C6 C5 N1 C15 -161.4(2) . . . . ?
C6 C7 C8 N1 -1.3(3) . . . . ?
C6 C7 C8 N2 -177.1(2) . . . . ?
C6 C7 C10 C9 175.6(3) . . . . ?
C6 C7 C10 C11 -3.5(5) . . . . ?
C7 C8 N1 C5 1.7(3) . . . . ?
C7 C8 N1 C15 160.6(2) . . . . ?
C7 C8 N2 C9 -0.6(3) . . . . ?
C7 C8 N2 C22 150.5(3) . . . . ?
C7 C8 N2 C22A -152.2(4) . . . . ?
C7 C10 C11 C12 179.6(2) . . . . ?
C8 C7 C10 C9 0.0(3) . . . . ?
C8 C7 C10 C11 -179.2(3) . . . . ?
C8 N2 C22 C23 115.2(4) . . . . ?
C8 N2 C22A C23A -115.6(6) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C9 N2 C22 C23 -99.2(4) . . . . ?
C9 N2 C22A C23A 96.4(6) . . . . ?
C10 C7 C8 N1 176.2(2) . . . . ?
C10 C7 C8 N2 0.4(3) . . . . ?
C10 C9 C14 C13 -0.2(5) . . . . ?
C10 C9 N2 C8 0.6(3) . . . . ?
C10 C9 N2 C22 -150.3(3) . . . . ?
C10 C9 N2 C22A 155.3(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C12 C13 C14 C9 0.3(5) . . . . ?
C14 C9 C10 C7 -179.5(3) . . . . ?
C14 C9 C10 C11 -0.2(4) . . . . ?
C14 C9 N2 C8 179.6(3) . . . . ?
C14 C9 N2 C22 28.7(5) . . . . ?
C14 C9 N2 C22A -25.6(6) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
C16 C15 C20 C19 0.9(4) . . . . ?
C16 C15 N1 C5 96.9(3) . . . . ?
C16 C15 N1 C8 -58.2(4) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C16 C17 C18 C21 179.9(3) . . . . ?
C17 C18 C19 C20 -0.4(4) . . . . ?
C18 C19 C20 C15 0.0(4) . . . . ?
C20 C15 C16 C17 -1.4(4) . . . . ?
C20 C15 N1 C5 -79.4(3) . . . . ?
C20 C15 N1 C8 125.5(3) . . . . ?
C21 C18 C19 C20 179.6(3) . . . . ?
N1 C5 C6 C1 -178.0(2) . . . . ?
N1 C5 C6 C7 0.8(3) . . . . ?
N1 C8 N2 C9 -175.2(3) . . . . ?
N1 C8 N2 C22 -24.1(5) . . . . ?
N1 C8 N2 C22A 33.2(6) . . . . ?
N1 C15 C16 C17 -177.7(2) . . . . ?
N1 C15 C20 C19 177.2(2) . . . . ?
N2 C8 N1 C5 176.3(3) . . . . ?
N2 C8 N1 C15 -24.8(5) . . . . ?
N2 C9 C10 C7 -0.3(3) . . . . ?
N2 C9 C10 C11 179.0(2) . . . . ?
N2 C9 C14 C13 -179.2(3) . . . . ?
N2 C22 C23 O1 70.3(6) . . . . ?
N2 C22A C23A O1A -169.4(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
