# 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. 
# 
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data_20230512_auto
_database_code_depnum_ccdc_archive 'CCDC 2330634'
loop_
_audit_author_name
_audit_author_address
'junlei wang'
;Guizhou Minzu University
China
;
_audit_update_record             
;
2024-02-03 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   14.0601(3)
_cell_length_b                   15.6594(4)
_cell_length_c                   7.7115(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.332(2)
_cell_angle_gamma                90
_cell_volume                     1664.76(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.644
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5041
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.273
_diffrn_reflns_theta_max         76.343
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.700
_diffrn_reflns_point_group_measured_fraction_full 0.760
_reflns_number_total             2454
_reflns_number_gt                2319
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.476
_reflns_Friedel_fraction_max     0.453
_reflns_Friedel_fraction_full    0.518

_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    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0382P)²+0.6703P] 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     SHELXL
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 713 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2454
_refine_ls_number_parameters     219
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.006
_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
O22 O 0.26683(18) 0.74838(13) 0.5058(4) 0.0584(6) Uani 1 1 d . . . . .
N8 N 0.45799(17) 0.51957(14) 0.4642(3) 0.0381(5) Uani 1 1 d . . . . .
O24 O 0.19296(18) 0.62391(17) 0.5304(4) 0.0657(7) Uani 1 1 d . . . . .
C21 C 0.2636(2) 0.66280(18) 0.5096(4) 0.0427(6) Uani 1 1 d . . . . .
C1 C 0.5118(2) 0.59461(16) 0.4715(3) 0.0361(6) Uani 1 1 d . . . . .
C3 C 0.3552(2) 0.62414(17) 0.4895(4) 0.0380(6) Uani 1 1 d . . . . .
C9 C 0.4767(2) 0.75276(16) 0.4938(4) 0.0378(6) Uani 1 1 d . . . . .
C2 C 0.4488(2) 0.66108(17) 0.4867(3) 0.0366(6) Uani 1 1 d . . . . .
C4 C 0.3651(2) 0.53652(17) 0.4754(4) 0.0386(6) Uani 1 1 d . . . . .
C14 C 0.5151(2) 0.78800(19) 0.3557(4) 0.0438(7) Uani 1 1 d . . . . .
H14 H 0.5192 0.7548 0.2574 0.053 Uiso 1 1 calc R U . . .
C15 C 0.6168(2) 0.59444(17) 0.4755(3) 0.0376(6) Uani 1 1 d . . . . .
C20 C 0.6601(2) 0.53516(19) 0.3803(4) 0.0454(7) Uani 1 1 d . . . . .
H20 H 0.6218 0.4948 0.3105 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4764(2) 0.42763(17) 0.4520(4) 0.0446(7) Uani 1 1 d . . . . .
H7A H 0.5333 0.4103 0.5376 0.053 Uiso 1 1 calc R U . . .
H7B H 0.4852 0.4121 0.3344 0.053 Uiso 1 1 calc R U . . .
C16 C 0.6768(2) 0.65402(19) 0.5778(4) 0.0455(7) Uani 1 1 d . . . . .
H16 H 0.6496 0.6943 0.6422 0.055 Uiso 1 1 calc R U . . .
C13 C 0.5470(3) 0.8719(2) 0.3639(5) 0.0572(8) Uani 1 1 d . . . . .
H13 H 0.5724 0.8947 0.2712 0.069 Uiso 1 1 calc R U . . .
C12 C 0.5413(3) 0.9215(2) 0.5078(6) 0.0669(11) Uani 1 1 d . . . . .
H12 H 0.5635 0.9776 0.5137 0.080 Uiso 1 1 calc R U . . .
C5 C 0.3065(2) 0.45683(18) 0.4660(4) 0.0474(7) Uani 1 1 d . . . . .
H5A H 0.2634 0.4510 0.3518 0.057 Uiso 1 1 calc R U . . .
H5B H 0.2686 0.4554 0.5583 0.057 Uiso 1 1 calc R U . . .
C10 C 0.4706(3) 0.8041(2) 0.6366(4) 0.0529(8) Uani 1 1 d . . . . .
H10 H 0.4446 0.7822 0.7293 0.063 Uiso 1 1 calc R U . . .
C19 C 0.7603(3) 0.5358(2) 0.3885(5) 0.0586(9) Uani 1 1 d . . . . .
H19 H 0.7882 0.4959 0.3244 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3842(3) 0.3877(2) 0.4936(5) 0.0527(8) Uani 1 1 d . . . . .
H6A H 0.3637 0.3397 0.4156 0.063 Uiso 1 1 calc R U . . .
H6B H 0.3958 0.3675 0.6148 0.063 Uiso 1 1 calc R U . . .
C17 C 0.7756(3) 0.6544(2) 0.5856(5) 0.0563(8) Uani 1 1 d . . . . .
H17 H 0.8142 0.6948 0.6548 0.068 Uiso 1 1 calc R U . . .
C18 C 0.8177(3) 0.5952(2) 0.4911(5) 0.0606(9) Uani 1 1 d . . . . .
H18 H 0.8844 0.5955 0.4969 0.073 Uiso 1 1 calc R U . . .
C11 C 0.5026(3) 0.8881(2) 0.6437(6) 0.0677(10) Uani 1 1 d . . . . .
H11 H 0.4979 0.9219 0.7408 0.081 Uiso 1 1 calc R U . . .
C23 C 0.1843(3) 0.7924(3) 0.5464(6) 0.0695(11) Uani 1 1 d . . . . .
H23A H 0.1263 0.7718 0.4710 0.104 Uiso 1 1 calc R U . . .
H23B H 0.1908 0.8526 0.5276 0.104 Uiso 1 1 calc R U . . .
H23C H 0.1807 0.7824 0.6677 0.104 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
O22 C21 1.341(4) . ?
O22 C23 1.436(4) . ?
N8 C4 1.351(4) . ?
N8 C1 1.393(3) . ?
N8 C7 1.469(3) . ?
O24 C21 1.202(4) . ?
C21 C3 1.459(4) . ?
C1 C2 1.387(4) . ?
C1 C15 1.470(4) . ?
C3 C4 1.386(4) . ?
C3 C2 1.441(4) . ?
C9 C10 1.380(4) . ?
C9 C14 1.399(4) . ?
C9 C2 1.487(4) . ?
C4 C5 1.490(4) . ?
C14 C13 1.386(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(4) . ?
C15 C20 1.395(4) . ?
C20 C19 1.398(5) . ?
C20 H20 0.9300 . ?
C7 C6 1.530(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9300 . ?
C13 C12 1.370(6) . ?
C13 H13 0.9300 . ?
C12 C11 1.376(6) . ?
C12 H12 0.9300 . ?
C5 C6 1.523(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C10 C11 1.387(5) . ?
C10 H10 0.9300 . ?
C19 C18 1.376(5) . ?
C19 H19 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C17 C18 1.383(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C11 H11 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C21 O22 C23 116.3(3) . . ?
C4 N8 C1 110.9(2) . . ?
C4 N8 C7 112.4(2) . . ?
C1 N8 C7 136.7(2) . . ?
O24 C21 O22 122.8(3) . . ?
O24 C21 C3 125.0(3) . . ?
O22 C21 C3 112.2(3) . . ?
C2 C1 N8 106.6(2) . . ?
C2 C1 C15 130.9(2) . . ?
N8 C1 C15 122.3(2) . . ?
C4 C3 C2 106.8(2) . . ?
C4 C3 C21 121.6(3) . . ?
C2 C3 C21 131.5(3) . . ?
C10 C9 C14 118.1(3) . . ?
C10 C9 C2 122.3(3) . . ?
C14 C9 C2 119.4(3) . . ?
C1 C2 C3 107.5(2) . . ?
C1 C2 C9 124.0(2) . . ?
C3 C2 C9 128.5(2) . . ?
N8 C4 C3 108.2(2) . . ?
N8 C4 C5 111.4(2) . . ?
C3 C4 C5 140.3(3) . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C16 C15 C20 117.7(3) . . ?
C16 C15 C1 120.3(2) . . ?
C20 C15 C1 122.0(3) . . ?
C15 C20 C19 120.8(3) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
N8 C7 C6 102.7(2) . . ?
N8 C7 H7A 111.2 . . ?
C6 C7 H7A 111.2 . . ?
N8 C7 H7B 111.2 . . ?
C6 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C4 C5 C6 102.4(3) . . ?
C4 C5 H5A 111.3 . . ?
C6 C5 H5A 111.3 . . ?
C4 C5 H5B 111.3 . . ?
C6 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C5 C6 C7 107.1(2) . . ?
C5 C6 H6A 110.3 . . ?
C7 C6 H6A 110.3 . . ?
C5 C6 H6B 110.3 . . ?
C7 C6 H6B 110.3 . . ?
H6A C6 H6B 108.5 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C23 O22 C21 O24 6.3(5) . . . . ?
C23 O22 C21 C3 -172.5(3) . . . . ?
C4 N8 C1 C2 -0.4(3) . . . . ?
C7 N8 C1 C2 -178.6(3) . . . . ?
C4 N8 C1 C15 175.3(2) . . . . ?
C7 N8 C1 C15 -2.8(4) . . . . ?
O24 C21 C3 C4 6.5(5) . . . . ?
O22 C21 C3 C4 -174.7(3) . . . . ?
O24 C21 C3 C2 -170.8(3) . . . . ?
O22 C21 C3 C2 7.9(5) . . . . ?
N8 C1 C2 C3 0.3(3) . . . . ?
C15 C1 C2 C3 -174.9(3) . . . . ?
N8 C1 C2 C9 -178.3(2) . . . . ?
C15 C1 C2 C9 6.4(5) . . . . ?
C4 C3 C2 C1 -0.2(3) . . . . ?
C21 C3 C2 C1 177.5(3) . . . . ?
C4 C3 C2 C9 178.4(3) . . . . ?
C21 C3 C2 C9 -3.9(5) . . . . ?
C10 C9 C2 C1 -119.7(3) . . . . ?
C14 C9 C2 C1 57.1(4) . . . . ?
C10 C9 C2 C3 61.9(4) . . . . ?
C14 C9 C2 C3 -121.2(3) . . . . ?
C1 N8 C4 C3 0.3(3) . . . . ?
C7 N8 C4 C3 178.9(2) . . . . ?
C1 N8 C4 C5 179.5(2) . . . . ?
C7 N8 C4 C5 -1.9(3) . . . . ?
C2 C3 C4 N8 -0.1(3) . . . . ?
C21 C3 C4 N8 -178.0(3) . . . . ?
C2 C3 C4 C5 -178.8(3) . . . . ?
C21 C3 C4 C5 3.2(6) . . . . ?
C10 C9 C14 C13 0.8(4) . . . . ?
C2 C9 C14 C13 -176.2(3) . . . . ?
C2 C1 C15 C16 31.7(4) . . . . ?
N8 C1 C15 C16 -142.8(3) . . . . ?
C2 C1 C15 C20 -148.9(3) . . . . ?
N8 C1 C15 C20 36.5(4) . . . . ?
C16 C15 C20 C19 0.2(4) . . . . ?
C1 C15 C20 C19 -179.1(3) . . . . ?
C4 N8 C7 C6 -10.6(3) . . . . ?
C1 N8 C7 C6 167.5(3) . . . . ?
C20 C15 C16 C17 -0.2(4) . . . . ?
C1 C15 C16 C17 179.2(3) . . . . ?
C9 C14 C13 C12 0.0(5) . . . . ?
C14 C13 C12 C11 -0.8(6) . . . . ?
N8 C4 C5 C6 13.6(3) . . . . ?
C3 C4 C5 C6 -167.7(4) . . . . ?
C14 C9 C10 C11 -0.8(5) . . . . ?
C2 C9 C10 C11 176.1(3) . . . . ?
C15 C20 C19 C18 0.0(5) . . . . ?
C4 C5 C6 C7 -19.6(3) . . . . ?
N8 C7 C6 C5 18.7(3) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C20 C19 C18 C17 -0.2(5) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C13 C12 C11 C10 0.8(6) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.034

_shelxl_version_number           2014-1



