# 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_20221021YZH_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2223581'
loop_
_audit_author_name
_audit_author_address
Yanzhenhui
;chengdu university of traditional chinese medicine
China
;
_audit_update_record             
;
2022-12-01 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 N2 O3'
_chemical_formula_weight         436.49

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 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.7238(3)
_cell_length_b                   13.4171(3)
_cell_length_c                   15.0267(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.1520(10)
_cell_angle_gamma                90
_cell_volume                     2333.60(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9539
_cell_measurement_theta_min      4.46
_cell_measurement_theta_max      67.93

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.650
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32293
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.443
_diffrn_reflns_theta_max         68.161
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4257
_reflns_number_gt                3288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0805P)²+0.6854P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4257
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.001

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
O001 O 0.91235(12) 0.30636(11) 0.51797(10) 0.0503(4) Uani 1 1 d . . . . .
C1 C 0.64991(15) 0.35297(13) 0.36866(12) 0.0350(4) Uani 1 1 d . . . . .
O002 O 0.65268(14) 0.27380(11) 0.56508(10) 0.0549(4) Uani 1 1 d . . . . .
O2 O 0.62409(17) 0.40190(11) 0.65480(11) 0.0653(5) Uani 1 1 d . . . . .
N004 N 0.74358(14) 0.60703(11) 0.49556(11) 0.0416(4) Uani 1 1 d . . . . .
N005 N 0.78414(14) 0.23029(12) 0.40678(11) 0.0420(4) Uani 1 1 d . . . . .
C007 C 0.67915(16) 0.25529(13) 0.35242(13) 0.0381(4) Uani 1 1 d . . . . .
C008 C 0.74326(15) 0.39796(13) 0.43883(12) 0.0344(4) Uani 1 1 d . . . . .
C009 C 0.69904(16) 0.43676(13) 0.52205(12) 0.0366(4) Uani 1 1 d . . . . .
C00A C 0.88160(16) 0.45796(13) 0.32970(13) 0.0379(4) Uani 1 1 d . . . . .
C00B C 0.55243(16) 0.39523(15) 0.32015(13) 0.0404(4) Uani 1 1 d . . . . .
H00B H 0.533036 0.460796 0.331161 0.048 Uiso 1 1 calc R U . . .
C00C C 0.73473(17) 0.70994(14) 0.51773(13) 0.0407(4) Uani 1 1 d . . . . .
C00D C 0.80945(16) 0.48169(14) 0.40010(12) 0.0363(4) Uani 1 1 d . . . . .
C00E C 0.82476(16) 0.30743(14) 0.46162(13) 0.0393(4) Uani 1 1 d . . . . .
C00F C 0.69718(16) 0.53430(14) 0.54266(13) 0.0396(4) Uani 1 1 d . . . . .
H00F H 0.662477 0.553276 0.591539 0.048 Uiso 1 1 calc R U . . .
C00G C 0.80478(17) 0.57599(14) 0.42740(13) 0.0406(4) Uani 1 1 d . . . . .
H00G H 0.844366 0.623968 0.399674 0.049 Uiso 1 1 calc R U . . .
C00H C 0.99763(18) 0.48458(16) 0.34313(14) 0.0463(5) Uani 1 1 d . . . . .
H00H H 1.030319 0.513549 0.397458 0.056 Uiso 1 1 calc R U . . .
C00I C 0.65703(17) 0.36228(15) 0.58041(13) 0.0425(5) Uani 1 1 d . . . . .
C00J C 0.83551(19) 0.41316(16) 0.24787(14) 0.0474(5) Uani 1 1 d . . . . .
H00J H 0.758108 0.394603 0.237155 0.057 Uiso 1 1 calc R U . . .
C00K C 0.63370(19) 0.74617(16) 0.54336(15) 0.0485(5) Uani 1 1 d . . . . .
H00K H 0.571648 0.703530 0.545475 0.058 Uiso 1 1 calc R U . . .
C00L C 0.48239(18) 0.33912(17) 0.25402(14) 0.0476(5) Uani 1 1 d . . . . .
C00M C 0.82598(18) 0.77443(16) 0.51378(16) 0.0510(5) Uani 1 1 d . . . . .
H00M H 0.894356 0.750770 0.497565 0.061 Uiso 1 1 calc R U . . .
C00N C 0.51407(19) 0.24167(17) 0.23987(15) 0.0509(5) Uani 1 1 d . . . . .
H00N H 0.468067 0.204229 0.195993 0.061 Uiso 1 1 calc R U . . .
C00O C 0.9047(2) 0.39622(17) 0.18252(15) 0.0563(6) Uani 1 1 d . . . . .
H00O H 0.873373 0.365745 0.128548 0.068 Uiso 1 1 calc R U . . .
C00P C 0.61156(19) 0.19763(15) 0.28842(14) 0.0481(5) Uani 1 1 d . . . . .
H00P H 0.630723 0.131787 0.278296 0.058 Uiso 1 1 calc R U . . .
C00Q C 1.0655(2) 0.46860(18) 0.27676(16) 0.0550(6) Uani 1 1 d . . . . .
H00Q H 1.142593 0.488095 0.286398 0.066 Uiso 1 1 calc R U . . .
C00R C 0.6254(2) 0.84555(17) 0.56570(17) 0.0569(6) Uani 1 1 d . . . . .
H00R H 0.558349 0.869088 0.584157 0.068 Uiso 1 1 calc R U . . .
C00S C 1.0189(2) 0.42400(17) 0.19674(17) 0.0561(6) Uani 1 1 d . . . . .
H00S H 1.064610 0.412707 0.152489 0.067 Uiso 1 1 calc R U . . .
C00T C 0.8150(2) 0.87418(17) 0.53404(18) 0.0606(6) Uani 1 1 d . . . . .
H00T H 0.875527 0.917789 0.529540 0.073 Uiso 1 1 calc R U . . .
C00U C 0.7153(2) 0.90979(17) 0.56090(17) 0.0599(6) Uani 1 1 d . . . . .
H00U H 0.709141 0.976696 0.575587 0.072 Uiso 1 1 calc R U . . .
C00V C 0.3755(2) 0.3838(2) 0.19962(19) 0.0749(8) Uani 1 1 d . . . . .
H00A H 0.385130 0.454648 0.195449 0.112 Uiso 1 1 calc R U . . .
H00C H 0.309939 0.369882 0.228557 0.112 Uiso 1 1 calc R U . . .
H00D H 0.363438 0.355450 0.140224 0.112 Uiso 1 1 calc R U . . .
C00W C 0.8368(2) 0.13256(18) 0.4111(2) 0.0701(7) Uani 1 1 d . . . . .
H00E H 0.857649 0.116305 0.353597 0.105 Uiso 1 1 calc R U . . .
H00I H 0.782942 0.084041 0.426440 0.105 Uiso 1 1 calc R U . . .
H00L H 0.904733 0.132459 0.456190 0.105 Uiso 1 1 calc R U . . .
C00X C 0.5813(4) 0.3328(2) 0.7146(2) 0.0920(11) Uani 1 1 d . . . . .
H00V H 0.511470 0.302558 0.684432 0.138 Uiso 1 1 calc R U . . .
H00W H 0.565592 0.367483 0.767210 0.138 Uiso 1 1 calc R U . . .
H00X H 0.638152 0.282029 0.732187 0.138 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
O001 C00E 1.223(2) . ?
C1 C00B 1.376(3) . ?
C1 C007 1.386(3) . ?
C1 C008 1.519(2) . ?
O002 C00I 1.209(2) . ?
O2 C00I 1.349(3) . ?
O2 C00X 1.437(3) . ?
N004 C00F 1.368(2) . ?
N004 C00G 1.404(2) . ?
N004 C00C 1.428(2) . ?
N005 C00E 1.361(3) . ?
N005 C007 1.405(2) . ?
N005 C00W 1.446(3) . ?
C007 C00P 1.382(3) . ?
C008 C009 1.520(3) . ?
C008 C00D 1.532(2) . ?
C008 C00E 1.550(3) . ?
C009 C00F 1.346(3) . ?
C009 C00I 1.466(3) . ?
C00A C00H 1.390(3) . ?
C00A C00J 1.398(3) . ?
C00A C00D 1.490(3) . ?
C00B C00L 1.403(3) . ?
C00B H00B 0.9300 . ?
C00C C00M 1.385(3) . ?
C00C C00K 1.390(3) . ?
C00D C00G 1.334(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H C00Q 1.388(3) . ?
C00H H00H 0.9300 . ?
C00J C00O 1.388(3) . ?
C00J H00J 0.9300 . ?
C00K C00R 1.382(3) . ?
C00K H00K 0.9300 . ?
C00L C00N 1.385(3) . ?
C00L C00V 1.507(3) . ?
C00M C00T 1.383(3) . ?
C00M H00M 0.9300 . ?
C00N C00P 1.387(3) . ?
C00N H00N 0.9300 . ?
C00O C00S 1.374(3) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q C00S 1.376(3) . ?
C00Q H00Q 0.9300 . ?
C00R C00U 1.372(3) . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00T C00U 1.381(3) . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00V H00A 0.9600 . ?
C00V H00C 0.9600 . ?
C00V H00D 0.9600 . ?
C00W H00E 0.9600 . ?
C00W H00I 0.9600 . ?
C00W H00L 0.9600 . ?
C00X H00V 0.9600 . ?
C00X H00W 0.9600 . ?
C00X H00X 0.9600 . ?

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
C00B C1 C007 120.27(17) . . ?
C00B C1 C008 130.54(16) . . ?
C007 C1 C008 109.08(15) . . ?
C00I O2 C00X 116.02(18) . . ?
C00F N004 C00G 117.21(16) . . ?
C00F N004 C00C 121.29(16) . . ?
C00G N004 C00C 121.43(16) . . ?
C00E N005 C007 111.11(15) . . ?
C00E N005 C00W 123.81(18) . . ?
C007 N005 C00W 124.79(17) . . ?
C00P C007 C1 121.43(18) . . ?
C00P C007 N005 128.56(18) . . ?
C1 C007 N005 109.97(15) . . ?
C1 C008 C009 113.88(15) . . ?
C1 C008 C00D 112.36(15) . . ?
C009 C008 C00D 108.73(14) . . ?
C1 C008 C00E 101.11(14) . . ?
C009 C008 C00E 111.45(15) . . ?
C00D C008 C00E 109.09(15) . . ?
C00F C009 C00I 120.40(18) . . ?
C00F C009 C008 122.86(17) . . ?
C00I C009 C008 116.74(16) . . ?
C00H C00A C00J 118.08(18) . . ?
C00H C00A C00D 119.67(17) . . ?
C00J C00A C00D 122.19(17) . . ?
C1 C00B C00L 119.81(18) . . ?
C1 C00B H00B 120.1 . . ?
C00L C00B H00B 120.1 . . ?
C00M C00C C00K 119.44(18) . . ?
C00M C00C N004 120.60(18) . . ?
C00K C00C N004 119.96(18) . . ?
C00G C00D C00A 118.47(17) . . ?
C00G C00D C008 122.05(17) . . ?
C00A C00D C008 119.48(15) . . ?
O001 C00E N005 125.79(18) . . ?
O001 C00E C008 125.63(17) . . ?
N005 C00E C008 108.56(15) . . ?
C009 C00F N004 123.52(18) . . ?
C009 C00F H00F 118.2 . . ?
N004 C00F H00F 118.2 . . ?
C00D C00G N004 123.81(18) . . ?
C00D C00G H00G 118.1 . . ?
N004 C00G H00G 118.1 . . ?
C00Q C00H C00A 121.0(2) . . ?
C00Q C00H H00H 119.5 . . ?
C00A C00H H00H 119.5 . . ?
O002 C00I O2 122.42(18) . . ?
O002 C00I C009 124.31(18) . . ?
O2 C00I C009 113.27(17) . . ?
C00O C00J C00A 120.3(2) . . ?
C00O C00J H00J 119.8 . . ?
C00A C00J H00J 119.8 . . ?
C00R C00K C00C 120.0(2) . . ?
C00R C00K H00K 120.0 . . ?
C00C C00K H00K 120.0 . . ?
C00N C00L C00B 118.31(19) . . ?
C00N C00L C00V 120.84(19) . . ?
C00B C00L C00V 120.8(2) . . ?
C00T C00M C00C 119.7(2) . . ?
C00T C00M H00M 120.1 . . ?
C00C C00M H00M 120.1 . . ?
C00L C00N C00P 122.71(19) . . ?
C00L C00N H00N 118.6 . . ?
C00P C00N H00N 118.6 . . ?
C00S C00O C00J 120.7(2) . . ?
C00S C00O H00O 119.7 . . ?
C00J C00O H00O 119.7 . . ?
C007 C00P C00N 117.46(19) . . ?
C007 C00P H00P 121.3 . . ?
C00N C00P H00P 121.3 . . ?
C00S C00Q C00H 120.2(2) . . ?
C00S C00Q H00Q 119.9 . . ?
C00H C00Q H00Q 119.9 . . ?
C00U C00R C00K 120.6(2) . . ?
C00U C00R H00R 119.7 . . ?
C00K C00R H00R 119.7 . . ?
C00O C00S C00Q 119.7(2) . . ?
C00O C00S H00S 120.2 . . ?
C00Q C00S H00S 120.2 . . ?
C00U C00T C00M 120.8(2) . . ?
C00U C00T H00T 119.6 . . ?
C00M C00T H00T 119.6 . . ?
C00R C00U C00T 119.4(2) . . ?
C00R C00U H00U 120.3 . . ?
C00T C00U H00U 120.3 . . ?
C00L C00V H00A 109.5 . . ?
C00L C00V H00C 109.5 . . ?
H00A C00V H00C 109.5 . . ?
C00L C00V H00D 109.5 . . ?
H00A C00V H00D 109.5 . . ?
H00C C00V H00D 109.5 . . ?
N005 C00W H00E 109.5 . . ?
N005 C00W H00I 109.5 . . ?
H00E C00W H00I 109.5 . . ?
N005 C00W H00L 109.5 . . ?
H00E C00W H00L 109.5 . . ?
H00I C00W H00L 109.5 . . ?
O2 C00X H00V 109.5 . . ?
O2 C00X H00W 109.5 . . ?
H00V C00X H00W 109.5 . . ?
O2 C00X H00X 109.5 . . ?
H00V C00X H00X 109.5 . . ?
H00W C00X H00X 109.5 . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.052

