# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2096456'
loop_
_audit_author_name
_audit_author_address
'Chuanhua Qu'
;Chongqing University of Arts and Sciences
China
;
_audit_update_record             
;
2021-07-14 deposited with the CCDC.	2021-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H27 N O'
_chemical_formula_weight         333.45

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      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                   9.4574(11)
_cell_length_b                   10.1927(12)
_cell_length_c                   21.398(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.088(2)
_cell_angle_gamma                90
_cell_volume                     2057.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4590
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.26

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.076
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10636
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.942
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3826
_reflns_number_gt                3021
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0657P)²+0.4471P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3826
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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
O1 O 0.35658(11) 0.64407(10) 0.15196(5) 0.0499(3) Uani 1 1 d . . . . .
N1 N 0.37298(13) 0.33035(12) 0.36133(5) 0.0451(3) Uani 1 1 d . . . . .
H1 H 0.3091 0.2707 0.3632 0.054 Uiso 1 1 calc R U . . .
C8 C 0.51244(13) 0.48404(12) 0.32489(6) 0.0341(3) Uani 1 1 d . . . . .
C11 C 0.58676(14) 0.56042(13) 0.28202(6) 0.0357(3) Uani 1 1 d . . . . .
H11 H 0.6736 0.5932 0.2982 0.043 Uiso 1 1 calc R U . . .
C13 C 0.41213(14) 0.56175(13) 0.18858(6) 0.0356(3) Uani 1 1 d . . . . .
C7 C 0.54921(14) 0.46642(13) 0.39062(6) 0.0369(3) Uani 1 1 d . . . . .
C9 C 0.40177(14) 0.39793(13) 0.30829(6) 0.0366(3) Uani 1 1 d . . . . .
C12 C 0.55132(14) 0.59283(12) 0.22160(6) 0.0356(3) Uani 1 1 d . . . . .
C15 C 0.33499(15) 0.36780(13) 0.24871(7) 0.0406(3) Uani 1 1 d . . . . .
H15 H 0.2788 0.2929 0.2470 0.049 Uiso 1 1 calc R U . . .
C4 C 0.65613(14) 0.53833(14) 0.43050(6) 0.0394(3) Uani 1 1 d . . . . .
C14 C 0.34162(14) 0.43308(13) 0.19369(6) 0.0380(3) Uani 1 1 d . . . . .
C10 C 0.46002(16) 0.37132(14) 0.41036(7) 0.0439(4) Uani 1 1 d . . . . .
H10 H 0.4595 0.3399 0.4511 0.053 Uiso 1 1 calc R U . . .
C20 C 0.65370(16) 0.67828(15) 0.18541(7) 0.0461(4) Uani 1 1 d . . . . .
C5 C 0.73768(16) 0.47503(17) 0.47816(7) 0.0503(4) Uani 1 1 d . . . . .
H5 H 0.7268 0.3852 0.4839 0.060 Uiso 1 1 calc R U . . .
C3 C 0.67661(17) 0.67207(16) 0.42348(7) 0.0510(4) Uani 1 1 d . . . . .
H3 H 0.6238 0.7171 0.3921 0.061 Uiso 1 1 calc R U . . .
C16 C 0.25888(18) 0.37952(16) 0.13400(7) 0.0536(4) Uani 1 1 d . . . . .
C2 C 0.7744(2) 0.73959(19) 0.46245(8) 0.0664(5) Uani 1 1 d . . . . .
H2 H 0.7867 0.8293 0.4569 0.080 Uiso 1 1 calc R U . . .
C6 C 0.83425(18) 0.5432(2) 0.51698(8) 0.0649(5) Uani 1 1 d . . . . .
H6 H 0.8870 0.4991 0.5488 0.078 Uiso 1 1 calc R U . . .
C23 C 0.6638(2) 0.6246(2) 0.11915(8) 0.0676(5) Uani 1 1 d . . . . .
H23A H 0.6981 0.5359 0.1214 0.101 Uiso 1 1 calc R U . . .
H23B H 0.7279 0.6778 0.0973 0.101 Uiso 1 1 calc R U . . .
H23C H 0.5717 0.6263 0.0972 0.101 Uiso 1 1 calc R U . . .
C1 C 0.8532(2) 0.6751(2) 0.50920(9) 0.0708(5) Uani 1 1 d . . . . .
H1A H 0.9190 0.7206 0.5354 0.085 Uiso 1 1 calc R U . . .
C22 C 0.6026(2) 0.82108(17) 0.18198(9) 0.0681(5) Uani 1 1 d . . . . .
H22A H 0.5106 0.8249 0.1600 0.102 Uiso 1 1 calc R U . . .
H22B H 0.6681 0.8729 0.1601 0.102 Uiso 1 1 calc R U . . .
H22C H 0.5973 0.8549 0.2236 0.102 Uiso 1 1 calc R U . . .
C21 C 0.80427(18) 0.6771(2) 0.21707(9) 0.0739(6) Uani 1 1 d . . . . .
H21A H 0.8049 0.7217 0.2566 0.111 Uiso 1 1 calc R U . . .
H21B H 0.8674 0.7208 0.1907 0.111 Uiso 1 1 calc R U . . .
H21C H 0.8348 0.5880 0.2237 0.111 Uiso 1 1 calc R U . . .
C19 C 0.2337(3) 0.23246(19) 0.13934(10) 0.0847(7) Uani 1 1 d . . . . .
H19A H 0.3227 0.1886 0.1483 0.127 Uiso 1 1 calc R U . . .
H19B H 0.1896 0.2002 0.1006 0.127 Uiso 1 1 calc R U . . .
H19C H 0.1729 0.2159 0.1725 0.127 Uiso 1 1 calc R U . . .
C17 C 0.3405(3) 0.4014(3) 0.07597(9) 0.0950(8) Uani 1 1 d . . . . .
H17A H 0.3476 0.4938 0.0680 0.142 Uiso 1 1 calc R U . . .
H17B H 0.2915 0.3594 0.0406 0.142 Uiso 1 1 calc R U . . .
H17C H 0.4339 0.3647 0.0828 0.142 Uiso 1 1 calc R U . . .
C18 C 0.1137(2) 0.4462(2) 0.12494(12) 0.0972(8) Uani 1 1 d . . . . .
H18A H 0.0634 0.4348 0.1620 0.146 Uiso 1 1 calc R U . . .
H18B H 0.0603 0.4076 0.0898 0.146 Uiso 1 1 calc R U . . .
H18C H 0.1263 0.5382 0.1173 0.146 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 1.2391(16) . ?
N1 C10 1.3526(19) . ?
N1 C9 1.3716(17) . ?
N1 H1 0.8600 . ?
C8 C9 1.3925(18) . ?
C8 C11 1.4260(18) . ?
C8 C7 1.4358(18) . ?
C11 C12 1.3532(19) . ?
C11 H11 0.9300 . ?
C13 C14 1.4788(19) . ?
C13 C12 1.4832(18) . ?
C7 C10 1.3713(19) . ?
C7 C4 1.4714(19) . ?
C9 C15 1.4155(19) . ?
C12 C20 1.5501(18) . ?
C15 C14 1.358(2) . ?
C15 H15 0.9300 . ?
C4 C3 1.387(2) . ?
C4 C5 1.392(2) . ?
C14 C16 1.5489(19) . ?
C10 H10 0.9300 . ?
C20 C23 1.529(2) . ?
C20 C21 1.533(2) . ?
C20 C22 1.534(2) . ?
C5 C6 1.378(2) . ?
C5 H5 0.9300 . ?
C3 C2 1.383(2) . ?
C3 H3 0.9300 . ?
C16 C19 1.523(2) . ?
C16 C17 1.525(3) . ?
C16 C18 1.532(3) . ?
C2 C1 1.372(3) . ?
C2 H2 0.9300 . ?
C6 C1 1.368(3) . ?
C6 H6 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C1 H1A 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C10 N1 C9 109.95(12) . . ?
C10 N1 H1 125.0 . . ?
C9 N1 H1 125.0 . . ?
C9 C8 C11 125.17(12) . . ?
C9 C8 C7 107.23(11) . . ?
C11 C8 C7 127.04(12) . . ?
C12 C11 C8 130.39(12) . . ?
C12 C11 H11 114.8 . . ?
C8 C11 H11 114.8 . . ?
O1 C13 C14 118.31(12) . . ?
O1 C13 C12 118.59(12) . . ?
C14 C13 C12 122.94(12) . . ?
C10 C7 C8 106.19(12) . . ?
C10 C7 C4 125.86(12) . . ?
C8 C7 C4 127.90(12) . . ?
N1 C9 C8 107.18(12) . . ?
N1 C9 C15 122.30(12) . . ?
C8 C9 C15 130.20(12) . . ?
C11 C12 C13 123.64(12) . . ?
C11 C12 C20 119.57(12) . . ?
C13 C12 C20 116.54(11) . . ?
C14 C15 C9 129.01(13) . . ?
C14 C15 H15 115.5 . . ?
C9 C15 H15 115.5 . . ?
C3 C4 C5 117.42(14) . . ?
C3 C4 C7 121.50(13) . . ?
C5 C4 C7 121.05(13) . . ?
C15 C14 C13 123.21(12) . . ?
C15 C14 C16 119.37(13) . . ?
C13 C14 C16 117.10(12) . . ?
N1 C10 C7 109.45(12) . . ?
N1 C10 H10 125.3 . . ?
C7 C10 H10 125.3 . . ?
C23 C20 C21 106.83(15) . . ?
C23 C20 C22 109.60(14) . . ?
C21 C20 C22 107.94(15) . . ?
C23 C20 C12 110.16(12) . . ?
C21 C20 C12 111.62(12) . . ?
C22 C20 C12 110.57(13) . . ?
C6 C5 C4 121.11(16) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C2 C3 C4 121.09(16) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C19 C16 C17 107.21(16) . . ?
C19 C16 C18 107.61(16) . . ?
C17 C16 C18 109.48(18) . . ?
C19 C16 C14 110.95(14) . . ?
C17 C16 C14 111.39(14) . . ?
C18 C16 C14 110.09(14) . . ?
C1 C2 C3 120.41(18) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C1 C6 C5 120.61(17) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C6 C1 C2 119.36(17) . . ?
C6 C1 H1A 120.3 . . ?
C2 C1 H1A 120.3 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C9 C8 C11 C12 17.6(2) . . . . ?
C7 C8 C11 C12 -172.15(14) . . . . ?
C9 C8 C7 C10 0.09(14) . . . . ?
C11 C8 C7 C10 -171.60(13) . . . . ?
C9 C8 C7 C4 -177.51(12) . . . . ?
C11 C8 C7 C4 10.8(2) . . . . ?
C10 N1 C9 C8 0.51(15) . . . . ?
C10 N1 C9 C15 174.60(13) . . . . ?
C11 C8 C9 N1 171.53(12) . . . . ?
C7 C8 C9 N1 -0.36(14) . . . . ?
C11 C8 C9 C15 -1.9(2) . . . . ?
C7 C8 C9 C15 -173.81(14) . . . . ?
C8 C11 C12 C13 6.1(2) . . . . ?
C8 C11 C12 C20 -179.89(13) . . . . ?
O1 C13 C12 C11 141.16(14) . . . . ?
C14 C13 C12 C11 -43.59(19) . . . . ?
O1 C13 C12 C20 -33.05(18) . . . . ?
C14 C13 C12 C20 142.20(13) . . . . ?
N1 C9 C15 C14 172.81(14) . . . . ?
C8 C9 C15 C14 -14.6(2) . . . . ?
C10 C7 C4 C3 -138.31(15) . . . . ?
C8 C7 C4 C3 38.8(2) . . . . ?
C10 C7 C4 C5 39.6(2) . . . . ?
C8 C7 C4 C5 -143.20(14) . . . . ?
C9 C15 C14 C13 -7.1(2) . . . . ?
C9 C15 C14 C16 179.58(14) . . . . ?
O1 C13 C14 C15 -141.54(14) . . . . ?
C12 C13 C14 C15 43.19(19) . . . . ?
O1 C13 C14 C16 31.91(18) . . . . ?
C12 C13 C14 C16 -143.36(13) . . . . ?
C9 N1 C10 C7 -0.47(16) . . . . ?
C8 C7 C10 N1 0.23(16) . . . . ?
C4 C7 C10 N1 177.89(12) . . . . ?
C11 C12 C20 C23 137.38(15) . . . . ?
C13 C12 C20 C23 -48.16(17) . . . . ?
C11 C12 C20 C21 18.9(2) . . . . ?
C13 C12 C20 C21 -166.67(14) . . . . ?
C11 C12 C20 C22 -101.31(15) . . . . ?
C13 C12 C20 C22 73.15(16) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C7 C4 C5 C6 -177.66(13) . . . . ?
C5 C4 C3 C2 0.0(2) . . . . ?
C7 C4 C3 C2 178.01(14) . . . . ?
C15 C14 C16 C19 -24.6(2) . . . . ?
C13 C14 C16 C19 161.65(15) . . . . ?
C15 C14 C16 C17 -143.99(17) . . . . ?
C13 C14 C16 C17 42.3(2) . . . . ?
C15 C14 C16 C18 94.37(19) . . . . ?
C13 C14 C16 C18 -79.34(18) . . . . ?
C4 C3 C2 C1 -0.2(3) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C5 C6 C1 C2 0.4(3) . . . . ?
C3 C2 C1 C6 0.0(3) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.029

