# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_20220928TJ_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2296784'
loop_
_audit_author_name
_audit_author_address
'weifang Zuo'
;ChengDu University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2023-09-22 deposited with the CCDC.	2024-03-09 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            'C21 H17 N O3'
_chemical_formula_weight         331.36

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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8129(2)
_cell_length_b                   24.2864(6)
_cell_length_c                   8.4619(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.0690(10)
_cell_angle_gamma                90
_cell_volume                     1721.81(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      5.28
_cell_measurement_theta_max      68.07

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.693
_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            30807
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.640
_diffrn_reflns_theta_max         68.340
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3157
_reflns_number_gt                2633
_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)+(0.0824P)²+0.4289P] 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         3157
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.38889(18) 0.44194(6) 0.85761(15) 0.0641(4) Uani 1 1 d . . . . .
O002 O 0.24980(19) 0.65418(6) 0.47973(17) 0.0671(4) Uani 1 1 d . . . . .
N003 N 0.2945(2) 0.46655(6) 0.35480(18) 0.0552(4) Uani 1 1 d . . . . .
O004 O 0.1805(2) 0.49395(7) 0.8624(2) 0.0835(5) Uani 1 1 d . . . . .
C005 C 0.2779(2) 0.45064(7) 0.5006(2) 0.0472(4) Uani 1 1 d . . . . .
C006 C 0.2745(2) 0.39013(7) 0.5255(2) 0.0492(4) Uani 1 1 d . . . . .
C007 C 0.2420(2) 0.56023(7) 0.4134(2) 0.0493(4) Uani 1 1 d . . . . .
C008 C 0.2227(2) 0.61996(7) 0.3687(2) 0.0512(4) Uani 1 1 d . . . . .
C009 C 0.2578(2) 0.48944(7) 0.6157(2) 0.0492(4) Uani 1 1 d . . . . .
C00A C 0.1704(2) 0.63754(7) 0.1915(2) 0.0512(4) Uani 1 1 d . . . . .
C00B C 0.2346(2) 0.54396(7) 0.5688(2) 0.0515(4) Uani 1 1 d . . . . .
H00B H 0.214106 0.569808 0.640634 0.062 Uiso 1 1 calc R U . . .
C00C C 0.2678(3) 0.47559(8) 0.7910(2) 0.0570(5) Uani 1 1 d . . . . .
C00D C 0.3687(3) 0.35542(8) 0.4651(2) 0.0602(5) Uani 1 1 d . . . . .
H00D H 0.435954 0.370056 0.410148 0.072 Uiso 1 1 calc R U . . .
C00E C 0.0732(2) 0.60540(8) 0.0646(2) 0.0611(5) Uani 1 1 d . . . . .
H00E H 0.042690 0.570427 0.087813 0.073 Uiso 1 1 calc R U . . .
C00F C 0.1720(2) 0.36703(8) 0.6035(3) 0.0602(5) Uani 1 1 d . . . . .
H00F H 0.107036 0.389822 0.642957 0.072 Uiso 1 1 calc R U . . .
C00G C 0.2797(2) 0.52002(8) 0.3154(2) 0.0549(5) Uani 1 1 d . . . . .
H00G H 0.295686 0.530896 0.216325 0.066 Uiso 1 1 calc R U . . .
C00H C 0.2144(3) 0.68974(8) 0.1537(3) 0.0612(5) Uani 1 1 d . . . . .
H00H H 0.278678 0.711856 0.237700 0.073 Uiso 1 1 calc R U . . .
C00I C 0.0215(3) 0.62529(10) -0.0965(3) 0.0747(6) Uani 1 1 d . . . . .
H00I H -0.044749 0.603802 -0.180877 0.090 Uiso 1 1 calc R U . . .
C00J C 0.1633(3) 0.70885(9) -0.0076(3) 0.0745(6) Uani 1 1 d . . . . .
H00J H 0.193606 0.743681 -0.032292 0.089 Uiso 1 1 calc R U . . .
C00K C 0.3628(3) 0.29890(10) 0.4866(3) 0.0748(6) Uani 1 1 d . . . . .
H00K H 0.427551 0.275865 0.447562 0.090 Uiso 1 1 calc R U . . .
C00L C 0.0673(3) 0.67634(10) -0.1324(3) 0.0789(7) Uani 1 1 d . . . . .
H00L H 0.033608 0.689170 -0.241266 0.095 Uiso 1 1 calc R U . . .
C00M C 0.1656(3) 0.31092(9) 0.6230(3) 0.0741(6) Uani 1 1 d . . . . .
H00M H 0.096377 0.296025 0.675233 0.089 Uiso 1 1 calc R U . . .
C00N C 0.2618(3) 0.27672(9) 0.5651(3) 0.0787(7) Uani 1 1 d . . . . .
H00N H 0.258264 0.238809 0.579123 0.094 Uiso 1 1 calc R U . . .
C00O C 0.4029(3) 0.42017(10) 1.0224(3) 0.0783(7) Uani 1 1 d . . . . .
H00A H 0.448722 0.447730 1.106630 0.094 Uiso 1 1 calc R U . . .
H00C H 0.298530 0.410133 1.028940 0.094 Uiso 1 1 calc R U . . .
C00P C 0.5046(4) 0.37247(13) 1.0486(3) 0.1072(11) Uani 1 1 d . . . . .
H00O H 0.456289 0.344962 0.967038 0.161 Uiso 1 1 calc R U . . .
H00P H 0.518821 0.357966 1.157812 0.161 Uiso 1 1 calc R U . . .
H00Q H 0.606419 0.382646 1.038520 0.161 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 C00C 1.323(2) . ?
O001 C00O 1.460(2) . ?
O002 C008 1.221(2) . ?
N003 C00G 1.337(2) . ?
N003 C005 1.344(2) . ?
O004 C00C 1.202(2) . ?
C005 C009 1.405(2) . ?
C005 C006 1.486(2) . ?
C006 C00D 1.387(3) . ?
C006 C00F 1.391(3) . ?
C007 C00G 1.387(3) . ?
C007 C00B 1.393(2) . ?
C007 C008 1.495(3) . ?
C008 C00A 1.488(3) . ?
C009 C00B 1.379(3) . ?
C009 C00C 1.497(2) . ?
C00A C00E 1.388(3) . ?
C00A C00H 1.392(3) . ?
C00B H00B 0.9300 . ?
C00D C00K 1.388(3) . ?
C00D H00D 0.9300 . ?
C00E C00I 1.383(3) . ?
C00E H00E 0.9300 . ?
C00F C00M 1.376(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H C00J 1.378(3) . ?
C00H H00H 0.9300 . ?
C00I C00L 1.367(3) . ?
C00I H00I 0.9300 . ?
C00J C00L 1.378(3) . ?
C00J H00J 0.9300 . ?
C00K C00N 1.375(4) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M C00N 1.381(4) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O C00P 1.439(4) . ?
C00O H00A 0.9700 . ?
C00O H00C 0.9700 . ?
C00P H00O 0.9600 . ?
C00P H00P 0.9600 . ?
C00P H00Q 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
C00C O001 C00O 116.66(16) . . ?
C00G N003 C005 118.59(15) . . ?
N003 C005 C009 121.11(16) . . ?
N003 C005 C006 115.30(15) . . ?
C009 C005 C006 123.53(15) . . ?
C00D C006 C00F 118.72(18) . . ?
C00D C006 C005 120.51(17) . . ?
C00F C006 C005 120.72(17) . . ?
C00G C007 C00B 117.04(16) . . ?
C00G C007 C008 124.14(16) . . ?
C00B C007 C008 118.61(16) . . ?
O002 C008 C00A 120.36(17) . . ?
O002 C008 C007 119.05(16) . . ?
C00A C008 C007 120.58(16) . . ?
C00B C009 C005 118.90(15) . . ?
C00B C009 C00C 117.33(15) . . ?
C005 C009 C00C 123.70(16) . . ?
C00E C00A C00H 118.90(18) . . ?
C00E C00A C008 122.85(17) . . ?
C00H C00A C008 118.17(17) . . ?
C009 C00B C007 119.86(16) . . ?
C009 C00B H00B 120.1 . . ?
C007 C00B H00B 120.1 . . ?
O004 C00C O001 124.92(17) . . ?
O004 C00C C009 124.40(19) . . ?
O001 C00C C009 110.64(16) . . ?
C006 C00D C00K 120.1(2) . . ?
C006 C00D H00D 119.9 . . ?
C00K C00D H00D 119.9 . . ?
C00I C00E C00A 120.11(19) . . ?
C00I C00E H00E 119.9 . . ?
C00A C00E H00E 119.9 . . ?
C00M C00F C006 120.9(2) . . ?
C00M C00F H00F 119.5 . . ?
C006 C00F H00F 119.5 . . ?
N003 C00G C007 123.88(16) . . ?
N003 C00G H00G 118.1 . . ?
C007 C00G H00G 118.1 . . ?
C00J C00H C00A 120.4(2) . . ?
C00J C00H H00H 119.8 . . ?
C00A C00H H00H 119.8 . . ?
C00L C00I C00E 120.4(2) . . ?
C00L C00I H00I 119.8 . . ?
C00E C00I H00I 119.8 . . ?
C00L C00J C00H 120.0(2) . . ?
C00L C00J H00J 120.0 . . ?
C00H C00J H00J 120.0 . . ?
C00N C00K C00D 120.5(2) . . ?
C00N C00K H00K 119.8 . . ?
C00D C00K H00K 119.8 . . ?
C00I C00L C00J 120.2(2) . . ?
C00I C00L H00L 119.9 . . ?
C00J C00L H00L 119.9 . . ?
C00F C00M C00N 120.0(2) . . ?
C00F C00M H00M 120.0 . . ?
C00N C00M H00M 120.0 . . ?
C00K C00N C00M 119.8(2) . . ?
C00K C00N H00N 120.1 . . ?
C00M C00N H00N 120.1 . . ?
C00P C00O O001 107.7(2) . . ?
C00P C00O H00A 110.2 . . ?
O001 C00O H00A 110.2 . . ?
C00P C00O H00C 110.2 . . ?
O001 C00O H00C 110.2 . . ?
H00A C00O H00C 108.5 . . ?
C00O C00P H00O 109.5 . . ?
C00O C00P H00P 109.5 . . ?
H00O C00P H00P 109.5 . . ?
C00O C00P H00Q 109.5 . . ?
H00O C00P H00Q 109.5 . . ?
H00P C00P H00Q 109.5 . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.042



