# Supplementary Information (SI) 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_20230409_8_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2fwhys
_database_code_depnum_ccdc_archive 'CCDC 2260766'
loop_
_audit_author_name
_audit_author_address
'Nan Wang'
;Nankai University
China
;
_audit_update_record             
;
2023-05-05 deposited with the CCDC.	2024-10-11 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N O2'
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.7871(6)
_cell_length_b                   15.5197(10)
_cell_length_c                   24.4352(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3332.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    298.30
_cell_measurement_theta_max      54.959
_cell_measurement_theta_min      4.958
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1153 before and 0.0727 after correction.
The Ratio of minimum to maximum transmission is 0.8198.
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    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            33641
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         2.625
_diffrn_ambient_temperature      298.30
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2488
_reflns_number_total             3394
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0189(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.054
_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)+(0.0532P)²+0.7132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1108
_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
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C14(H14),
 C15(H15), C17(H17), C18(H18), C21(H21)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C19(H19A,H19B,H19C)
;
_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
O1 O -0.05654(12) 0.36741(7) 0.35278(4) 0.0392(3) Uani 1 1 d . . . . .
O2 O 0.06154(13) 0.25594(7) 0.31354(5) 0.0487(3) Uani 1 1 d . . . . .
N1 N 0.33443(15) 0.59526(8) 0.38361(5) 0.0382(3) Uani 1 1 d . . . . .
H1 H 0.400696 0.631903 0.372238 0.046 Uiso 1 1 calc R U . . .
C1 C 0.23701(16) 0.62220(9) 0.42557(6) 0.0288(3) Uani 1 1 d . . . . .
C2 C 0.81854(18) 0.60560(11) 0.28524(7) 0.0409(4) Uani 1 1 d . . . . .
H2 H 0.863822 0.623223 0.252714 0.049 Uiso 1 1 calc R U . . .
C3 C 0.10167(19) 0.59861(10) 0.50958(6) 0.0377(4) Uani 1 1 d . . . . .
H3 H 0.072556 0.561907 0.537785 0.045 Uiso 1 1 calc R U . . .
C4 C 0.20302(17) 0.46351(9) 0.35751(5) 0.0301(3) Uani 1 1 d . . . . .
H4 H 0.115698 0.482461 0.375329 0.036 Uiso 1 1 calc R U . . .
C5 C 0.0450(2) 0.83174(11) 0.46817(8) 0.0534(5) Uani 1 1 d . . . . .
H5A H 0.097629 0.862727 0.496409 0.080 Uiso 1 1 calc R U . . .
H5B H -0.062629 0.834315 0.474749 0.080 Uiso 1 1 calc R U . . .
H5C H 0.067353 0.857212 0.433281 0.080 Uiso 1 1 calc R U . . .
C6 C 0.18783(16) 0.70737(9) 0.42655(6) 0.0301(3) Uani 1 1 d . . . . .
H6 H 0.217168 0.744219 0.398451 0.036 Uiso 1 1 calc R U . . .
C7 C 0.68204(17) 0.56116(10) 0.28395(6) 0.0361(4) Uani 1 1 d . . . . .
H7 H 0.637377 0.548163 0.250443 0.043 Uiso 1 1 calc R U . . .
C8 C 0.33411(16) 0.51431(9) 0.35843(5) 0.0295(3) Uani 1 1 d . . . . .
C9 C 0.88774(19) 0.62387(10) 0.33459(7) 0.0428(4) Uani 1 1 d . . . . .
H9 H 0.979784 0.653428 0.335347 0.051 Uiso 1 1 calc R U . . .
C10 C 0.46574(16) 0.48586(9) 0.33083(5) 0.0300(3) Uani 1 1 d . . . . .
C11 C 0.05221(18) 0.68306(10) 0.50988(6) 0.0380(4) Uani 1 1 d . . . . .
H11 H -0.010524 0.702587 0.537916 0.046 Uiso 1 1 calc R U . . .
C12 C 0.61084(17) 0.53572(9) 0.33215(6) 0.0312(3) Uani 1 1 d . . . . .
C13 C 0.06424(17) 0.32917(9) 0.33065(6) 0.0327(3) Uani 1 1 d . . . . .
C14 C 0.19374(17) 0.56758(9) 0.46808(6) 0.0346(4) Uani 1 1 d . . . . .
H14 H 0.226545 0.510609 0.468554 0.042 Uiso 1 1 calc R U . . .
C15 C 0.68170(18) 0.55511(10) 0.38189(6) 0.0374(4) Uani 1 1 d . . . . .
H15 H 0.635634 0.538972 0.414590 0.045 Uiso 1 1 calc R U . . .
C16 C 0.09619(17) 0.73897(9) 0.46826(6) 0.0342(4) Uani 1 1 d . . . . .
C17 C 0.81962(19) 0.59805(10) 0.38295(7) 0.0423(4) Uani 1 1 d . . . . .
H17 H 0.866690 0.609590 0.416242 0.051 Uiso 1 1 calc R U . . .
C18 C 0.45872(18) 0.40831(10) 0.30195(6) 0.0347(4) Uani 1 1 d . . . . .
H18 H 0.543329 0.390510 0.282070 0.042 Uiso 1 1 calc R U . . .
C19 C -0.19302(19) 0.31617(11) 0.35568(7) 0.0472(4) Uani 1 1 d . . . . .
H19A H -0.222578 0.298972 0.319465 0.071 Uiso 1 1 calc R U . . .
H19B H -0.273140 0.349504 0.371957 0.071 Uiso 1 1 calc R U . . .
H19C H -0.174273 0.265882 0.377539 0.071 Uiso 1 1 calc R U . . .
C20 C 0.20162(17) 0.38509(9) 0.33030(5) 0.0298(3) Uani 1 1 d . . . . .
C21 C 0.33010(18) 0.35727(10) 0.30199(6) 0.0344(4) Uani 1 1 d . . . . .
H21 H 0.329238 0.305012 0.283370 0.041 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
O1 C13 1.3308(18) . ?
O1 C19 1.4407(19) . ?
O2 C13 1.2113(17) . ?
N1 H1 0.8600 . ?
N1 C1 1.3996(18) . ?
N1 C8 1.3988(18) . ?
C1 C6 1.391(2) . ?
C1 C14 1.394(2) . ?
C2 H2 0.9300 . ?
C2 C7 1.384(2) . ?
C2 C9 1.380(2) . ?
C3 H3 0.9300 . ?
C3 C11 1.381(2) . ?
C3 C14 1.384(2) . ?
C4 H4 0.9300 . ?
C4 C8 1.396(2) . ?
C4 C20 1.3869(19) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C5 C16 1.508(2) . ?
C6 H6 0.9300 . ?
C6 C16 1.388(2) . ?
C7 H7 0.9300 . ?
C7 C12 1.391(2) . ?
C8 C10 1.410(2) . ?
C9 H9 0.9300 . ?
C9 C17 1.384(2) . ?
C10 C12 1.492(2) . ?
C10 C18 1.397(2) . ?
C11 H11 0.9300 . ?
C11 C16 1.392(2) . ?
C12 C15 1.399(2) . ?
C13 C20 1.487(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C17 1.383(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C21 1.380(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.393(2) . ?
C21 H21 0.9300 . ?

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
C13 O1 C19 115.95(12) . . ?
C1 N1 H1 116.9 . . ?
C8 N1 H1 116.9 . . ?
C8 N1 C1 126.10(12) . . ?
C6 C1 N1 119.12(13) . . ?
C6 C1 C14 118.71(13) . . ?
C14 C1 N1 122.09(13) . . ?
C7 C2 H2 119.9 . . ?
C9 C2 H2 119.9 . . ?
C9 C2 C7 120.29(15) . . ?
C11 C3 H3 119.4 . . ?
C11 C3 C14 121.22(14) . . ?
C14 C3 H3 119.4 . . ?
C8 C4 H4 119.6 . . ?
C20 C4 H4 119.6 . . ?
C20 C4 C8 120.71(13) . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C16 C5 H5A 109.5 . . ?
C16 C5 H5B 109.5 . . ?
C16 C5 H5C 109.5 . . ?
C1 C6 H6 119.0 . . ?
C16 C6 C1 121.91(13) . . ?
C16 C6 H6 119.0 . . ?
C2 C7 H7 119.6 . . ?
C2 C7 C12 120.80(14) . . ?
C12 C7 H7 119.6 . . ?
N1 C8 C10 119.34(13) . . ?
C4 C8 N1 121.06(13) . . ?
C4 C8 C10 119.50(13) . . ?
C2 C9 H9 120.1 . . ?
C2 C9 C17 119.74(15) . . ?
C17 C9 H9 120.1 . . ?
C8 C10 C12 121.91(12) . . ?
C18 C10 C8 118.39(13) . . ?
C18 C10 C12 119.71(13) . . ?
C3 C11 H11 120.0 . . ?
C3 C11 C16 120.03(14) . . ?
C16 C11 H11 120.0 . . ?
C7 C12 C10 120.90(13) . . ?
C7 C12 C15 118.33(14) . . ?
C15 C12 C10 120.72(13) . . ?
O1 C13 C20 112.93(12) . . ?
O2 C13 O1 122.89(14) . . ?
O2 C13 C20 124.17(14) . . ?
C1 C14 H14 120.2 . . ?
C3 C14 C1 119.61(14) . . ?
C3 C14 H14 120.2 . . ?
C12 C15 H15 119.7 . . ?
C17 C15 C12 120.66(14) . . ?
C17 C15 H15 119.7 . . ?
C6 C16 C5 120.60(14) . . ?
C6 C16 C11 118.51(14) . . ?
C11 C16 C5 120.89(14) . . ?
C9 C17 H17 119.9 . . ?
C15 C17 C9 120.16(15) . . ?
C15 C17 H17 119.9 . . ?
C10 C18 H18 119.0 . . ?
C21 C18 C10 122.03(14) . . ?
C21 C18 H18 119.0 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C20 C13 121.11(13) . . ?
C4 C20 C21 120.19(14) . . ?
C21 C20 C13 118.69(13) . . ?
C18 C21 C20 119.10(13) . . ?
C18 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?

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
O1 C13 C20 C4 8.27(19) . . . . ?
O1 C13 C20 C21 -171.75(12) . . . . ?
O2 C13 C20 C4 -170.62(14) . . . . ?
O2 C13 C20 C21 9.4(2) . . . . ?
N1 C1 C6 C16 -177.34(13) . . . . ?
N1 C1 C14 C3 177.61(14) . . . . ?
N1 C8 C10 C12 6.0(2) . . . . ?
N1 C8 C10 C18 -174.48(13) . . . . ?
C1 N1 C8 C4 24.8(2) . . . . ?
C1 N1 C8 C10 -158.89(14) . . . . ?
C1 C6 C16 C5 179.90(15) . . . . ?
C1 C6 C16 C11 -0.4(2) . . . . ?
C2 C7 C12 C10 -178.43(14) . . . . ?
C2 C7 C12 C15 -0.9(2) . . . . ?
C2 C9 C17 C15 -0.9(2) . . . . ?
C3 C11 C16 C5 -179.27(15) . . . . ?
C3 C11 C16 C6 1.1(2) . . . . ?
C4 C8 C10 C12 -177.63(12) . . . . ?
C4 C8 C10 C18 1.9(2) . . . . ?
C4 C20 C21 C18 0.7(2) . . . . ?
C6 C1 C14 C3 1.0(2) . . . . ?
C7 C2 C9 C17 -0.4(2) . . . . ?
C7 C12 C15 C17 -0.4(2) . . . . ?
C8 N1 C1 C6 -144.37(14) . . . . ?
C8 N1 C1 C14 39.0(2) . . . . ?
C8 C4 C20 C13 177.93(13) . . . . ?
C8 C4 C20 C21 -2.1(2) . . . . ?
C8 C10 C12 C7 -124.61(15) . . . . ?
C8 C10 C12 C15 57.90(19) . . . . ?
C8 C10 C18 C21 -3.3(2) . . . . ?
C9 C2 C7 C12 1.3(2) . . . . ?
C10 C12 C15 C17 177.15(14) . . . . ?
C10 C18 C21 C20 2.0(2) . . . . ?
C11 C3 C14 C1 -0.3(2) . . . . ?
C12 C10 C18 C21 176.23(13) . . . . ?
C12 C15 C17 C9 1.3(2) . . . . ?
C13 C20 C21 C18 -179.29(13) . . . . ?
C14 C1 C6 C16 -0.6(2) . . . . ?
C14 C3 C11 C16 -0.7(2) . . . . ?
C18 C10 C12 C7 55.90(19) . . . . ?
C18 C10 C12 C15 -121.59(15) . . . . ?
C19 O1 C13 O2 0.3(2) . . . . ?
C19 O1 C13 C20 -178.56(12) . . . . ?
C20 C4 C8 N1 177.02(13) . . . . ?
C20 C4 C8 C10 0.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
