# 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. 
# 
#######################################################################

data_exp_8930
_audit_block_doi                 10.5517/ccdc.csd.cc2kcl3n
_database_code_depnum_ccdc_archive 'CCDC 2364621'
loop_
_audit_author_name
_audit_author_address
'Ning Chen'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2024-06-22 deposited with the CCDC.	2024-09-05 downloaded from the CCDC.
;
_audit_creation_date             2024-01-23
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H21 N O'
_chemical_formula_sum            'C22 H21 N O'
_chemical_formula_weight         315.40
_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 0.0033 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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.1511(11)
_cell_length_b                   9.4553(12)
_cell_length_c                   10.6950(12)
_cell_angle_alpha                104.602(10)
_cell_angle_beta                 96.752(10)
_cell_angle_gamma                99.319(10)
_cell_volume                     871.45(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1551
_cell_measurement_temperature    114.55(10)
_cell_measurement_theta_max      28.1100
_cell_measurement_theta_min      3.9840
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.37
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5969
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.36
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      114.55(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.8107
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414  -77.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00   20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -99.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega   32.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414 -178.0000   30.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega  -11.00   31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414  -57.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega   52.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   57.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega    0.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   57.0000  150.0000 79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0408295000
_diffrn_orient_matrix_UB_12      -0.0409827000
_diffrn_orient_matrix_UB_13      -0.0627418000
_diffrn_orient_matrix_UB_21      -0.0578616000
_diffrn_orient_matrix_UB_22      0.0410669000
_diffrn_orient_matrix_UB_23      0.0108978000
_diffrn_orient_matrix_UB_31      0.0364423000
_diffrn_orient_matrix_UB_32      0.0537105000
_diffrn_orient_matrix_UB_33      -0.0278549000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2475
_reflns_number_total             3341
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0408P)²+0.1352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1203
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28224(13) 0.96339(15) 0.05057(12) 0.0318(3) Uani 1 1 d . . .
N1 N 0.57725(14) 0.99623(16) 0.18126(14) 0.0266(4) Uani 1 1 d . . .
H1 H 0.6055 0.9953 0.1071 0.032 Uiso 1 1 d R . .
C10 C 0.17846(17) 0.88490(19) 0.21910(16) 0.0220(4) Uani 1 1 d . . .
C17 C 0.60780(17) 1.1346(2) 0.27210(16) 0.0232(4) Uani 1 1 d . . .
C22 C 0.72501(18) 1.2445(2) 0.26196(17) 0.0267(4) Uani 1 1 d . . .
H22 H 0.7788 1.2240 0.1932 0.032 Uiso 1 1 calc R . .
C2 C 0.45759(17) 0.8761(2) 0.18111(17) 0.0246(4) Uani 1 1 d . . .
H2 H 0.4654 0.8605 0.2686 0.030 Uiso 1 1 calc R . .
C11 C 0.05268(18) 0.9478(2) 0.19917(17) 0.0265(4) Uani 1 1 d . . .
H11 H 0.0478 1.0040 0.1394 0.032 Uiso 1 1 calc R . .
C3 C 0.47746(18) 0.7342(2) 0.08212(17) 0.0280(4) Uani 1 1 d . . .
H3A H 0.4587 0.7464 -0.0053 0.034 Uiso 1 1 calc R . .
H3B H 0.5810 0.7233 0.0989 0.034 Uiso 1 1 calc R . .
C1 C 0.30179(18) 0.9116(2) 0.14379(16) 0.0238(4) Uani 1 1 d . . .
C14 C 0.06332(18) 0.7802(2) 0.37581(17) 0.0287(4) Uani 1 1 d . . .
H14 H 0.0673 0.7232 0.4349 0.034 Uiso 1 1 calc R . .
C12 C -0.06451(18) 0.9272(2) 0.26751(18) 0.0297(4) Uani 1 1 d . . .
H12 H -0.1470 0.9706 0.2534 0.036 Uiso 1 1 calc R . .
C18 C 0.52989(18) 1.1688(2) 0.37765(16) 0.0270(4) Uani 1 1 d . . .
H18 H 0.4519 1.0979 0.3871 0.032 Uiso 1 1 calc R . .
C4 C 0.37623(18) 0.5931(2) 0.08573(16) 0.0248(4) Uani 1 1 d . . .
C15 C 0.18169(18) 0.8007(2) 0.30864(16) 0.0263(4) Uani 1 1 d . . .
H15 H 0.2643 0.7578 0.3235 0.032 Uiso 1 1 calc R . .
C16 C -0.19113(19) 0.8207(2) 0.4296(2) 0.0380(5) Uani 1 1 d . . .
H16A H -0.2585 0.7282 0.3841 0.057 Uiso 1 1 calc R . .
H16B H -0.2437 0.9014 0.4346 0.057 Uiso 1 1 calc R . .
H16C H -0.1535 0.8181 0.5165 0.057 Uiso 1 1 calc R . .
C19 C 0.5690(2) 1.3080(2) 0.46771(17) 0.0302(4) Uani 1 1 d . . .
H19 H 0.5163 1.3294 0.5372 0.036 Uiso 1 1 calc R . .
C21 C 0.7615(2) 1.3825(2) 0.35254(18) 0.0334(5) Uani 1 1 d . . .
H21 H 0.8389 1.4544 0.3436 0.040 Uiso 1 1 calc R . .
C9 C 0.24041(19) 0.5373(2) 0.00094(18) 0.0300(4) Uani 1 1 d . . .
H9 H 0.2116 0.5877 -0.0591 0.036 Uiso 1 1 calc R . .
C13 C -0.06151(18) 0.8434(2) 0.35644(17) 0.0271(4) Uani 1 1 d . . .
C5 C 0.4168(2) 0.5155(2) 0.17384(18) 0.0320(5) Uani 1 1 d . . .
H5 H 0.5080 0.5504 0.2306 0.038 Uiso 1 1 calc R . .
C20 C 0.6841(2) 1.4157(2) 0.45700(18) 0.0346(5) Uani 1 1 d . . .
H20 H 0.7093 1.5087 0.5184 0.042 Uiso 1 1 calc R . .
C8 C 0.1474(2) 0.4083(2) 0.0043(2) 0.0376(5) Uani 1 1 d . . .
H8 H 0.0573 0.3718 -0.0539 0.045 Uiso 1 1 calc R . .
C6 C 0.3235(2) 0.3869(2) 0.1787(2) 0.0421(5) Uani 1 1 d . . .
H6 H 0.3518 0.3364 0.2388 0.051 Uiso 1 1 calc R . .
C7 C 0.1883(2) 0.3337(2) 0.0939(2) 0.0416(5) Uani 1 1 d . . .
H7 H 0.1251 0.2477 0.0973 0.050 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
O1 C1 1.224(2) . ?
N1 H1 0.8605 . ?
N1 C17 1.382(2) . ?
N1 C2 1.444(2) . ?
C10 C11 1.397(2) . ?
C10 C1 1.487(2) . ?
C10 C15 1.392(2) . ?
C17 C22 1.402(2) . ?
C17 C18 1.402(2) . ?
C22 H22 0.9300 . ?
C22 C21 1.378(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.537(2) . ?
C2 C1 1.547(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.508(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(2) . ?
C14 C13 1.390(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(2) . ?
C4 C9 1.388(2) . ?
C4 C5 1.385(2) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C13 1.512(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.389(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C20 H20 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.378(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(3) . ?
C7 H7 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
C17 N1 H1 115.1 . . ?
C17 N1 C2 123.67(13) . . ?
C2 N1 H1 116.5 . . ?
C11 C10 C1 118.33(15) . . ?
C15 C10 C11 118.20(14) . . ?
C15 C10 C1 123.47(15) . . ?
N1 C17 C22 119.09(14) . . ?
N1 C17 C18 122.78(15) . . ?
C22 C17 C18 118.09(16) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.85(16) . . ?
C21 C22 H22 119.6 . . ?
N1 C2 H2 109.1 . . ?
N1 C2 C3 107.90(12) . . ?
N1 C2 C1 111.33(14) . . ?
C3 C2 H2 109.1 . . ?
C3 C2 C1 110.19(14) . . ?
C1 C2 H2 109.1 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.55(16) . . ?
C12 C11 H11 119.7 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.46(13) . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
O1 C1 C10 120.38(15) . . ?
O1 C1 C2 118.31(14) . . ?
C10 C1 C2 121.31(14) . . ?
C15 C14 H14 119.4 . . ?
C15 C14 C13 121.11(17) . . ?
C13 C14 H14 119.4 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.29(16) . . ?
C13 C12 H12 119.4 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.01(16) . . ?
C19 C18 H18 120.0 . . ?
C9 C4 C3 121.05(16) . . ?
C5 C4 C3 120.71(16) . . ?
C5 C4 C9 118.24(17) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.69(16) . . ?
C14 C15 H15 119.7 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.62(16) . . ?
C20 C19 H19 119.2 . . ?
C22 C21 H21 119.6 . . ?
C22 C21 C20 120.81(17) . . ?
C20 C21 H21 119.6 . . ?
C4 C9 H9 119.4 . . ?
C8 C9 C4 121.15(18) . . ?
C8 C9 H9 119.4 . . ?
C14 C13 C16 121.16(17) . . ?
C12 C13 C14 118.15(15) . . ?
C12 C13 C16 120.69(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.98(18) . . ?
C6 C5 H5 119.5 . . ?
C19 C20 C21 118.62(18) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C9 C8 H8 120.1 . . ?
C7 C8 C9 119.89(18) . . ?
C7 C8 H8 120.1 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.86(19) . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 119.88(18) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?

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
N1 C17 C22 C21 -178.30(16) . . . . ?
N1 C17 C18 C19 177.93(16) . . . . ?
N1 C2 C3 C4 170.66(14) . . . . ?
N1 C2 C1 O1 45.1(2) . . . . ?
N1 C2 C1 C10 -134.47(16) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C17 N1 C2 C3 -170.04(15) . . . . ?
C17 N1 C2 C1 68.93(19) . . . . ?
C17 C22 C21 C20 0.7(3) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C22 C17 C18 C19 0.3(2) . . . . ?
C22 C21 C20 C19 -0.5(3) . . . . ?
C2 N1 C17 C22 -178.81(15) . . . . ?
C2 N1 C17 C18 3.6(2) . . . . ?
C2 C3 C4 C9 95.1(2) . . . . ?
C2 C3 C4 C5 -85.02(19) . . . . ?
C11 C10 C1 O1 -13.0(2) . . . . ?
C11 C10 C1 C2 166.50(16) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C11 C12 C13 C16 -179.47(17) . . . . ?
C3 C2 C1 O1 -74.6(2) . . . . ?
C3 C2 C1 C10 105.85(17) . . . . ?
C3 C4 C9 C8 -179.87(16) . . . . ?
C3 C4 C5 C6 179.25(16) . . . . ?
C1 C10 C11 C12 -179.53(16) . . . . ?
C1 C10 C15 C14 179.92(16) . . . . ?
C1 C2 C3 C4 -67.60(19) . . . . ?
C18 C17 C22 C21 -0.6(2) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C4 C9 C8 C7 0.7(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C15 C10 C11 C12 0.4(3) . . . . ?
C15 C10 C1 O1 167.07(16) . . . . ?
C15 C10 C1 C2 -13.4(2) . . . . ?
C15 C14 C13 C12 0.2(3) . . . . ?
C15 C14 C13 C16 179.86(17) . . . . ?
C9 C4 C5 C6 -0.9(3) . . . . ?
C9 C8 C7 C6 -1.1(3) . . . . ?
C13 C14 C15 C10 -0.3(3) . . . . ?
C5 C4 C9 C8 0.3(3) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?

