# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_fast
_database_code_depnum_ccdc_archive 'CCDC 2213771'
loop_
_audit_author_name
_audit_author_address
zhangwei
;Zhongshan Institute for Drug Discovery
China
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;
_audit_creation_date             2022-10-18
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_chemical_name_common            ?
_chemical_name_systematic        
; 
 ? 
;
_chemical_formula_moiety         'C22 H21 N O3'
_chemical_formula_sum            'C22 H21 N O3'
_chemical_formula_weight         347.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.3096(4)
_cell_length_b                   10.8544(4)
_cell_length_c                   12.5557(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.697(2)
_cell_angle_gamma                90.00
_cell_volume                     1813.10(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9711
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      76.1820
_cell_measurement_theta_min      3.2700
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.8991
_exptl_absorpt_correction_T_min  0.8650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
; 
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16770
_diffrn_reflns_theta_full        76.54
_diffrn_reflns_theta_max         76.54
_diffrn_reflns_theta_min         3.32
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3058
_reflns_number_total             3689
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     411
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.1063
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0672P)²+5.7871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2709
_refine_ls_wR_factor_ref         0.2778
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2. Rigid bond restraints 
 O, N1, O1, C2, C3, O3, C4, C5, C6, C7, C8, C9, C10, C11, C13, C14, C15, C, 
 C16, C17, C19, C23, C1, C12, C18, C20, C23', C18', C19', C1', C12', C20' 
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002 
3. Uiso/Uaniso restraints and constraints 
O \\sim N1 \\sim O1 \\sim C2 \\sim C3 \\sim O3 \\sim C4 \\sim C5 \\sim C6 \\sim 
C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C13 \\sim C14 \\sim C15 \\sim C 
\\sim C16 \\sim C17 \\sim C19 \\sim C23 \\sim C1 \\sim C12 \\sim C18 \\sim C20 
\\sim C23' \\sim C18' \\sim C19' \\sim C1' \\sim C12' \\sim C20': within 2A 
with sigma of 0.002 and sigma for terminal atoms of 0.002 
4. Others 
 Sof(C23')=Sof(H23')=Sof(C18')=Sof(H18')=Sof(C19')=Sof(C1')=Sof(H1')=Sof(C12')= 
 Sof(H12')=Sof(C20')=Sof(H20')=1-FVAR(1) 
 Sof(C19)=Sof(H19)=Sof(C23)=Sof(C1)=Sof(H1A)=Sof(C12)=Sof(H12)=Sof(C18)= 
 Sof(H18)=Sof(C20)=Sof(H20)=FVAR(1) 
5.a Ternary CH refined with riding coordinates: 
 C2(H2), C13(H13) 
5.b Secondary CH2 refined with riding coordinates: 
 C(HA,HB), C16(H16A,H16B) 
5.c Aromatic/amide H refined with riding coordinates: 
 N1(H1), C7(H7), C9(H9), C11(H11), C14(H14), C15(H15), C19(H19), C1(H1A), 
 C12(H12), C18(H18), C20(H20), C23'(H23'), C18'(H18'), C1'(H1'), C12'(H12'), 
 C20'(H20') 
5.d Fitted hexagon refined as free rotating group: 
 C23'(C18',C19',C1',C12',C20') 
5.e Idealised Me refined as rotating group: 
 C17(H17A,H17B,H17C) 
5.f Idealised tetrahedral OH refined as rotating group: 
 O(H) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O O 0.7193(2) 0.0664(3) 0.6613(2) 0.0462(7) Uani 1 d . . . U
H H 0.7798 0.0526 0.6672 0.069 Uiso 1 calc . . GR .
N1 N 0.9072(2) 0.0689(4) 0.3948(3) 0.0424(7) Uani 1 d A . . U
H1 H 0.9707 0.0544 0.4001 0.051 Uiso 1 calc . . R .
O1 O 0.8908(2) 0.0014(3) 0.5649(2) 0.0463(7) Uani 1 d . . . U
C2 C 0.6819(3) 0.0202(4) 0.5622(3) 0.0391(6) Uani 1 d . . . U
H2 H 0.6134 0.0517 0.5512 0.047 Uiso 1 calc . . R .
C3 C 0.7434(3) 0.0646(4) 0.4690(3) 0.0371(6) Uani 1 d . . . U
O3 O 0.6761(3) -0.5036(3) 0.5458(3) 0.0580(7) Uani 1 d . . . U
C4 C 0.6762(3) -0.1205(4) 0.5594(3) 0.0388(6) Uani 1 d . . . U
C5 C 0.6722(4) -0.3773(4) 0.5454(4) 0.0472(7) Uani 1 d . . . U
C6 C 0.7034(3) 0.1125(4) 0.3757(3) 0.0385(6) Uani 1 d . . . U
C7 C 0.7696(3) 0.1393(4) 0.2916(3) 0.0411(7) Uani 1 d A . . U
H7 H 0.7439 0.1734 0.2286 0.049 Uiso 1 calc . . R .
C8 C 0.8498(3) 0.0427(4) 0.4813(3) 0.0405(6) Uani 1 d . . . U
C9 C 0.7110(3) -0.1930(4) 0.6431(3) 0.0416(7) Uani 1 d . . . U
H9 H 0.7357 -0.1555 0.7051 0.050 Uiso 1 calc . . R .
C10 C 0.8701(3) 0.1159(5) 0.3020(4) 0.0450(6) Uani 1 d . . . U
C11 C 0.7098(3) -0.3203(4) 0.6367(4) 0.0449(7) Uani 1 d . . . U
H11 H 0.7342 -0.3674 0.6936 0.054 Uiso 1 calc . . R .
C13 C 0.5937(3) 0.1342(4) 0.3585(4) 0.0427(7) Uani 1 d . . . U
H13 H 0.5551 0.1322 0.4238 0.051 Uiso 1 calc . . R .
C14 C 0.6342(3) -0.3069(4) 0.4621(4) 0.0462(7) Uani 1 d . . . U
H14 H 0.6070 -0.3446 0.4013 0.055 Uiso 1 calc . . R .
C15 C 0.6369(3) -0.1801(4) 0.4696(4) 0.0433(7) Uani 1 d . . . U
H15 H 0.6117 -0.1332 0.4129 0.052 Uiso 1 calc . . R .
C C 0.5388(3) 0.0830(5) 0.2618(4) 0.0472(8) Uani 1 d . . . U
HA H 0.5781 0.0417 0.2087 0.057 Uiso 1 calc . . R .
HB H 0.4723 0.0489 0.2713 0.057 Uiso 1 calc . . R .
C16 C 0.5513(3) 0.2175(5) 0.2739(4) 0.0480(8) Uani 1 d . . . U
H16A H 0.4924 0.2656 0.2904 0.058 Uiso 1 calc . . R .
H16B H 0.5982 0.2584 0.2280 0.058 Uiso 1 calc . . R .
C17 C 0.6455(5) -0.5680(5) 0.4534(5) 0.0671(10) Uani 1 d . . . U
H17A H 0.6847 -0.5414 0.3947 0.101 Uiso 1 calc . . GR .
H17B H 0.5757 -0.5520 0.4378 0.101 Uiso 1 calc . . GR .
H17C H 0.6553 -0.6548 0.4645 0.101 Uiso 1 calc . . GR .
C19 C 1.0951(5) 0.2283(7) 0.1499(5) 0.0555(8) Uani 0.797(4) d A 1 . U
H19 H 1.1575 0.2643 0.1642 0.067 Uiso 0.797(4) calc A 1 R .
C23 C 0.9393(5) 0.1467(7) 0.2128(5) 0.0503(7) Uani 0.797(4) d A 1 . U
C1 C 0.9079(4) 0.1283(6) 0.1079(5) 0.0528(8) Uani 0.797(4) d A 1 . U
H1A H 0.8442 0.0966 0.0926 0.063 Uiso 0.797(4) calc A 1 R .
C12 C 0.9710(4) 0.1571(7) 0.0256(5) 0.0551(8) Uani 0.797(4) d A 1 . U
H12 H 0.9501 0.1423 -0.0446 0.066 Uiso 0.797(4) calc A 1 R .
C18 C 1.0340(4) 0.1962(6) 0.2336(5) 0.0529(7) Uani 0.797(4) d A 1 . U
H18 H 1.0567 0.2079 0.3037 0.063 Uiso 0.797(4) calc A 1 R .
C20 C 1.0642(5) 0.2072(7) 0.0471(5) 0.0557(8) Uani 0.797(4) d A 1 . U
H20 H 1.1061 0.2268 -0.0084 0.067 Uiso 0.797(4) calc A 1 R .
C23' C 1.0834(10) 0.0287(13) 0.1283(12) 0.0537(10) Uani 0.203(4) d A 2 . U
H23' H 1.1273 -0.0360 0.1158 0.064 Uiso 0.203(4) calc A 2 R .
C18' C 1.0130(12) 0.0184(13) 0.2074(12) 0.0518(9) Uani 0.203(4) d A 2 G U
H18' H 1.0099 -0.0531 0.2479 0.062 Uiso 0.203(4) calc A 2 R .
C19' C 0.9474(11) 0.1151(16) 0.2261(12) 0.0508(7) Uani 0.203(4) d A 2 G U
C1' C 0.9521(11) 0.2221(13) 0.1656(13) 0.0531(8) Uani 0.203(4) d A 2 G U
H1' H 0.9081 0.2868 0.1781 0.064 Uiso 0.203(4) calc A 2 R .
C12' C 1.0224(12) 0.2324(13) 0.0864(12) 0.0543(8) Uani 0.203(4) d A 2 G U
H12' H 1.0255 0.3039 0.0459 0.065 Uiso 0.203(4) calc A 2 R .
C20' C 1.0881(11) 0.1357(16) 0.0678(11) 0.0550(9) Uani 0.203(4) d A 2 G U
H20' H 1.1351 0.1425 0.0148 0.066 Uiso 0.203(4) calc A 2 R .


_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
O C2 1.419(5) . ?
N1 C8 1.376(5) . ?
N1 C10 1.353(6) . ?
O1 C8 1.252(5) . ?
C2 C3 1.525(5) . ?
C2 C4 1.529(6) . ?
C3 C6 1.375(6) . ?
C3 C8 1.439(5) . ?
O3 C5 1.372(6) . ?
O3 C17 1.405(6) . ?
C4 C9 1.382(6) . ?
C4 C15 1.389(6) . ?
C5 C11 1.383(6) . ?
C5 C14 1.379(6) . ?
C6 C7 1.426(6) . ?
C6 C13 1.489(5) . ?
C7 C10 1.363(6) . ?
C9 C11 1.383(7) . ?
C10 C23 1.509(7) . ?
C10 C19' 1.423(11) . ?
C13 C 1.505(6) . ?
C13 C16 1.493(6) . ?
C14 C15 1.380(7) . ?
C C16 1.477(7) . ?
C19 C18 1.393(8) . ?
C19 C20 1.362(9) . ?
C23 C1 1.384(9) . ?
C23 C18 1.388(9) . ?
C1 C12 1.386(8) . ?
C12 C20 1.374(9) . ?
C23' C18' 1.3900 . ?
C23' C20' 1.3900 . ?
C18' C19' 1.3900 . ?
C19' C1' 1.3900 . ?
C1' C12' 1.3900 . ?
C12' C20' 1.3900 . ?

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
C10 N1 C8 124.1(3) . . ?
O C2 C3 112.2(3) . . ?
O C2 C4 112.9(4) . . ?
C3 C2 C4 109.0(3) . . ?
C6 C3 C2 124.7(3) . . ?
C6 C3 C8 120.6(4) . . ?
C8 C3 C2 114.5(4) . . ?
C5 O3 C17 118.9(4) . . ?
C9 C4 C2 122.4(4) . . ?
C9 C4 C15 117.5(4) . . ?
C15 C4 C2 120.0(4) . . ?
O3 C5 C11 115.6(4) . . ?
O3 C5 C14 124.7(4) . . ?
C14 C5 C11 119.7(4) . . ?
C3 C6 C7 118.5(4) . . ?
C3 C6 C13 122.5(4) . . ?
C7 C6 C13 119.0(4) . . ?
C10 C7 C6 121.1(4) . . ?
N1 C8 C3 116.7(4) . . ?
O1 C8 N1 119.8(4) . . ?
O1 C8 C3 123.5(4) . . ?
C4 C9 C11 121.4(4) . . ?
N1 C10 C7 119.0(4) . . ?
N1 C10 C23 120.5(4) . . ?
N1 C10 C19' 108.8(8) . . ?
C7 C10 C23 120.4(4) . . ?
C7 C10 C19' 131.6(8) . . ?
C19' C10 C23 15.1(7) . . ?
C5 C11 C9 119.9(4) . . ?
C6 C13 C 120.6(4) . . ?
C6 C13 C16 123.2(4) . . ?
C16 C13 C 59.0(3) . . ?
C5 C14 C15 119.5(4) . . ?
C14 C15 C4 121.9(4) . . ?
C16 C C13 60.1(3) . . ?
C C16 C13 60.9(3) . . ?
C20 C19 C18 120.4(6) . . ?
C1 C23 C10 120.0(6) . . ?
C1 C23 C18 118.8(5) . . ?
C18 C23 C10 121.1(6) . . ?
C23 C1 C12 120.3(6) . . ?
C20 C12 C1 120.4(6) . . ?
C23 C18 C19 120.1(6) . . ?
C19 C20 C12 120.0(6) . . ?
C18' C23' C20' 120.0 . . ?
C23' C18' C19' 120.0 . . ?
C18' C19' C10 126.0(10) . . ?
C1' C19' C10 114.0(10) . . ?
C1' C19' C18' 120.0 . . ?
C19' C1' C12' 120.0 . . ?
C20' C12' C1' 120.0 . . ?
C12' C20' C23' 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O C2 C3 C6 -132.7(4) . . . . ?
O C2 C3 C8 52.7(5) . . . . ?
O C2 C4 C9 -4.3(5) . . . . ?
O C2 C4 C15 177.1(3) . . . . ?
N1 C10 C23 C1 144.1(6) . . . . ?
N1 C10 C23 C18 -37.4(9) . . . . ?
N1 C10 C19' C18' 44.7(14) . . . . ?
N1 C10 C19' C1' -137.2(8) . . . . ?
C2 C3 C6 C7 -174.1(4) . . . . ?
C2 C3 C6 C13 4.3(7) . . . . ?
C2 C3 C8 N1 173.2(4) . . . . ?
C2 C3 C8 O1 -6.4(6) . . . . ?
C2 C4 C9 C11 -176.6(4) . . . . ?
C2 C4 C15 C14 177.2(4) . . . . ?
C3 C2 C4 C9 121.2(4) . . . . ?
C3 C2 C4 C15 -57.4(5) . . . . ?
C3 C6 C7 C10 1.4(7) . . . . ?
C3 C6 C13 C -127.4(5) . . . . ?
C3 C6 C13 C16 161.7(4) . . . . ?
O3 C5 C11 C9 178.7(4) . . . . ?
O3 C5 C14 C15 -178.1(4) . . . . ?
C4 C2 C3 C6 101.5(5) . . . . ?
C4 C2 C3 C8 -73.2(5) . . . . ?
C4 C9 C11 C5 -0.7(7) . . . . ?
C5 C14 C15 C4 -0.6(7) . . . . ?
C6 C3 C8 N1 -1.7(6) . . . . ?
C6 C3 C8 O1 178.7(4) . . . . ?
C6 C7 C10 N1 -1.5(7) . . . . ?
C6 C7 C10 C23 -179.1(5) . . . . ?
C6 C7 C10 C19' 168.3(11) . . . . ?
C6 C13 C C16 -112.7(5) . . . . ?
C6 C13 C16 C 108.5(5) . . . . ?
C7 C6 C13 C 51.0(6) . . . . ?
C7 C6 C13 C16 -19.8(7) . . . . ?
C7 C10 C23 C1 -38.4(9) . . . . ?
C7 C10 C23 C18 140.1(6) . . . . ?
C7 C10 C19' C18' -125.8(11) . . . . ?
C7 C10 C19' C1' 52.3(15) . . . . ?
C8 N1 C10 C7 -0.1(7) . . . . ?
C8 N1 C10 C23 177.4(5) . . . . ?
C8 N1 C10 C19' -172.1(9) . . . . ?
C8 C3 C6 C7 0.3(6) . . . . ?
C8 C3 C6 C13 178.7(4) . . . . ?
C9 C4 C15 C14 -1.4(6) . . . . ?
C10 N1 C8 O1 -178.7(4) . . . . ?
C10 N1 C8 C3 1.7(7) . . . . ?
C10 C23 C1 C12 179.7(6) . . . . ?
C10 C23 C18 C19 -177.5(6) . . . . ?
C10 C19' C1' C12' -178.2(15) . . . . ?
C11 C5 C14 C15 1.9(7) . . . . ?
C13 C6 C7 C10 -177.1(4) . . . . ?
C14 C5 C11 C9 -1.3(7) . . . . ?
C15 C4 C9 C11 2.0(6) . . . . ?
C17 O3 C5 C11 -175.9(4) . . . . ?
C17 O3 C5 C14 4.2(7) . . . . ?
C23 C10 C19' C18' -172(5) . . . . ?
C23 C10 C19' C1' 6(3) . . . . ?
C23 C1 C12 C20 -1.8(11) . . . . ?
C1 C23 C18 C19 1.0(11) . . . . ?
C1 C12 C20 C19 0.4(11) . . . . ?
C18 C19 C20 C12 1.8(11) . . . . ?
C18 C23 C1 C12 1.1(11) . . . . ?
C20 C19 C18 C23 -2.5(11) . . . . ?
C23' C18' C19' C10 178.0(17) . . . . ?
C23' C18' C19' C1' 0.0 . . . . ?
C18' C23' C20' C12' 0.0 . . . . ?
C18' C19' C1' C12' 0.0 . . . . ?
C19' C10 C23 C1 103(4) . . . . ?
C19' C10 C23 C18 -79(4) . . . . ?
C19' C1' C12' C20' 0.0 . . . . ?
C1' C12' C20' C23' 0.0 . . . . ?
C20' C23' C18' C19' 0.0 . . . . ?

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 2234440'
loop_
_audit_author_name
_audit_author_address
A
;Chinese Academy of Sciences, Shanghai Institue of Materia Medica
China
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;
_audit_creation_date             2022-02-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N O2'
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   14.0628(8)
_cell_length_b                   9.8424(7)
_cell_length_c                   11.6643(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.207(2)
_cell_angle_gamma                90
_cell_volume                     1472.51(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3227
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.2349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1667 before and 0.0851 after correction. The Ratio of minimum to maximum transmission is 0.3151. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10699
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.608
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'D8 VENTURE'
_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                2098
_reflns_number_total             2991
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2991
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.075
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1846
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C18(H18), C11(H11), C16(H16), C19(H19), C3(H3), C15(H15), C17(H17),
 C4(H4), C7(H7), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O2 O 0.60189(11) 0.06725(14) 0.48612(14) 0.0320(4) Uani 1 1 d . . . . .
O1 O 0.71109(12) 0.23203(18) 0.39891(15) 0.0407(5) Uani 1 1 d . . . . .
H1 H 0.679529 0.158005 0.392248 0.061 Uiso 1 1 calc GR . . . .
N1 N 0.50002(12) 0.18332(17) 0.56169(16) 0.0264(4) Uani 1 1 d . . . . .
H1A H 0.458656 0.112108 0.544736 0.032 Uiso 1 1 calc R . . . .
C10 C 0.62976(15) 0.4039(2) 0.61634(19) 0.0263(5) Uani 1 1 d . . . . .
C8 C 0.65141(15) 0.2929(2) 0.55980(19) 0.0262(5) Uani 1 1 d . . . . .
C13 C 0.47465(15) 0.2945(2) 0.61427(18) 0.0250(5) Uani 1 1 d . . . . .
C1 C 0.74348(16) 0.2824(2) 0.5233(2) 0.0295(5) Uani 1 1 d . . . . .
H1B H 0.769268 0.377077 0.523175 0.035 Uiso 1 1 calc R . . . .
C9 C 0.58526(15) 0.1758(2) 0.53389(19) 0.0258(5) Uani 1 1 d . . . . .
C18 C 0.29084(15) 0.2139(2) 0.5539(2) 0.0307(5) Uani 1 1 d . . . . .
H18 H 0.298236 0.152552 0.495164 0.037 Uiso 1 1 calc R . . . .
C2 C 0.83452(15) 0.2019(2) 0.6182(2) 0.0288(5) Uani 1 1 d . . . . .
C14 C 0.37582(15) 0.2930(2) 0.63087(19) 0.0275(5) Uani 1 1 d . . . . .
C11 C 0.53942(15) 0.4043(2) 0.64196(19) 0.0274(5) Uani 1 1 d . . . . .
H11 H 0.523807 0.482363 0.678987 0.033 Uiso 1 1 calc R . . . .
C16 C 0.26746(18) 0.3904(2) 0.7252(2) 0.0361(6) Uani 1 1 d . . . . .
H16 H 0.259524 0.450845 0.784176 0.043 Uiso 1 1 calc R . . . .
C12 C 0.69985(17) 0.5265(2) 0.6565(2) 0.0351(5) Uani 1 1 d . . . . .
H12A H 0.757723 0.508462 0.737773 0.053 Uiso 1 1 calc GR . . . .
H12B H 0.659940 0.604935 0.664225 0.053 Uiso 1 1 calc GR . . . .
H12C H 0.727466 0.545949 0.593525 0.053 Uiso 1 1 calc GR . . . .
C19 C 0.19586(16) 0.2249(2) 0.5631(2) 0.0349(6) Uani 1 1 d . . . . .
H19 H 0.138601 0.170865 0.510492 0.042 Uiso 1 1 calc R . . . .
C3 C 0.85723(17) 0.2058(2) 0.7460(2) 0.0337(5) Uani 1 1 d . . . . .
H3 H 0.813765 0.256512 0.774693 0.040 Uiso 1 1 calc R . . . .
C15 C 0.36238(17) 0.3800(2) 0.7174(2) 0.0320(5) Uani 1 1 d . . . . .
H15 H 0.419541 0.432987 0.771876 0.038 Uiso 1 1 calc R . . . .
C17 C 0.18368(17) 0.3130(2) 0.6473(2) 0.0366(6) Uani 1 1 d . . . . .
H17 H 0.118087 0.320860 0.652155 0.044 Uiso 1 1 calc R . . . .
C4 C 0.94234(17) 0.1366(2) 0.8320(2) 0.0398(6) Uani 1 1 d . . . . .
H4 H 0.957329 0.141161 0.919118 0.048 Uiso 1 1 calc R . . . .
C7 C 0.89899(18) 0.1262(2) 0.5789(2) 0.0416(6) Uani 1 1 d . . . . .
H7 H 0.885361 0.122745 0.492137 0.050 Uiso 1 1 calc R . . . .
C6 C 0.98298(19) 0.0557(3) 0.6653(3) 0.0500(7) Uani 1 1 d . . . . .
H6 H 1.025668 0.002810 0.636994 0.060 Uiso 1 1 calc R . . . .
C5 C 1.00544(18) 0.0611(3) 0.7917(3) 0.0466(7) Uani 1 1 d . . . . .
H5 H 1.063763 0.013380 0.850506 0.056 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C9 1.270(2) . ?
O1 H1 0.8400 . ?
O1 C1 1.420(3) . ?
N1 H1A 0.8800 . ?
N1 C13 1.372(3) . ?
N1 C9 1.366(3) . ?
C10 C8 1.373(3) . ?
C10 C11 1.419(3) . ?
C10 C12 1.506(3) . ?
C8 C1 1.523(3) . ?
C8 C9 1.434(3) . ?
C13 C14 1.480(3) . ?
C13 C11 1.364(3) . ?
C1 H1B 1.0000 . ?
C1 C2 1.527(3) . ?
C18 H18 0.9500 . ?
C18 C14 1.400(3) . ?
C18 C19 1.387(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.389(3) . ?
C14 C15 1.395(3) . ?
C11 H11 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.378(3) . ?
C16 C17 1.384(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C17 1.373(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.380(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.376(4) . ?
C5 H5 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 H1 109.5 . . ?
C13 N1 H1A 117.8 . . ?
C9 N1 H1A 117.8 . . ?
C9 N1 C13 124.34(17) . . ?
C8 C10 C11 119.83(18) . . ?
C8 C10 C12 122.76(19) . . ?
C11 C10 C12 117.39(19) . . ?
C10 C8 C1 124.70(17) . . ?
C10 C8 C9 119.2(2) . . ?
C9 C8 C1 116.05(18) . . ?
N1 C13 C14 118.73(17) . . ?
C11 C13 N1 117.86(19) . . ?
C11 C13 C14 123.30(18) . . ?
O1 C1 C8 110.84(16) . . ?
O1 C1 H1B 106.7 . . ?
O1 C1 C2 112.45(18) . . ?
C8 C1 H1B 106.7 . . ?
C8 C1 C2 112.89(17) . . ?
C2 C1 H1B 106.7 . . ?
O2 C9 N1 119.16(17) . . ?
O2 C9 C8 123.26(19) . . ?
N1 C9 C8 117.57(18) . . ?
C14 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C19 C18 C14 120.2(2) . . ?
C3 C2 C1 121.24(19) . . ?
C7 C2 C1 120.4(2) . . ?
C7 C2 C3 118.3(2) . . ?
C18 C14 C13 121.47(19) . . ?
C15 C14 C13 120.11(18) . . ?
C15 C14 C18 118.2(2) . . ?
C10 C11 H11 119.5 . . ?
C13 C11 C10 121.07(19) . . ?
C13 C11 H11 119.5 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C19 H19 119.6 . . ?
C17 C19 C18 120.8(2) . . ?
C17 C19 H19 119.6 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.6 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C16 C17 H17 120.2 . . ?
C19 C17 C16 119.7(2) . . ?
C19 C17 H17 120.2 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
