# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2259639'
loop_
_audit_author_name
_audit_author_address
'Li Jiajun'
;Nanjing University
China
;
_audit_update_record             
;
2023-04-28 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_audit_creation_date             2023-04-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 N O'
_chemical_formula_sum            'C22 H23 N O'
_chemical_formula_weight         317.41
_chemical_absolute_configuration ad
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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      tetragonal
_space_group_IT_number           79
_space_group_name_H-M_alt        'I 4'
_space_group_name_Hall           'I 4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'

_cell_length_a                   19.4725(6)
_cell_length_b                   19.4725(6)
_cell_length_c                   9.2892(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3522.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6916
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.84
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1129 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.8744.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_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  0.0387
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11057
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.044
_diffrn_reflns_theta_min         2.792
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2960
_reflns_number_total             3197
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1223 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+0.5052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0764
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
1.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C16(H16), C1(H1), C15(H15), C4(H4), C2(H2), C17(H17), C18(H18), C3(H3)
1.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C20(H20A,H20B,H20C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -0.96512(7) -0.78515(8) -0.6036(2) 0.0445(4) Uani 1 1 d . . . . .
N1 N -0.85689(8) -0.82457(8) -0.56815(19) 0.0288(4) Uani 1 1 d . . . . .
C6 C -0.74892(9) -0.58919(9) -0.5304(2) 0.0250(4) Uani 1 1 d . . . . .
C14 C -0.76750(9) -0.74924(9) -0.4713(2) 0.0246(4) Uani 1 1 d . . . . .
C7 C -0.81257(9) -0.62663(9) -0.4924(2) 0.0242(4) Uani 1 1 d . . . . .
C13 C -0.81876(9) -0.69432(9) -0.4729(2) 0.0235(4) Uani 1 1 d . . . . .
C5 C -0.71523(10) -0.60658(10) -0.6571(2) 0.0301(5) Uani 1 1 d . . . . .
H5 H -0.732552 -0.643070 -0.714439 0.036 Uiso 1 1 calc R . . . .
C16 C -0.65453(10) -0.79502(11) -0.4221(3) 0.0341(5) Uani 1 1 d . . . . .
H16 H -0.609119 -0.788673 -0.387158 0.041 Uiso 1 1 calc R . . . .
C19 C -0.78858(10) -0.81472(10) -0.5196(2) 0.0251(4) Uani 1 1 d . . . . .
C1 C -0.72237(11) -0.53568(10) -0.4482(2) 0.0345(5) Uani 1 1 d . . . . .
H1 H -0.744303 -0.522886 -0.360870 0.041 Uiso 1 1 calc R . . . .
C21 C -0.90833(10) -0.77719(10) -0.5497(2) 0.0297(5) Uani 1 1 d . . . . .
C11 C -0.93270(10) -0.65180(10) -0.4953(3) 0.0317(5) Uani 1 1 d . . . . .
H11A H -0.971986 -0.644884 -0.429228 0.038 Uiso 1 1 calc R . . . .
H11B H -0.950570 -0.656350 -0.594613 0.038 Uiso 1 1 calc R . . . .
C15 C -0.70074(10) -0.74106(10) -0.4219(2) 0.0301(5) Uani 1 1 d . . . . .
H15 H -0.686451 -0.697439 -0.387276 0.036 Uiso 1 1 calc R . . . .
C8 C -0.88243(10) -0.59044(10) -0.4854(2) 0.0288(4) Uani 1 1 d . . . . .
C12 C -0.89238(9) -0.71631(10) -0.4527(2) 0.0259(4) Uani 1 1 d . . . . .
C4 C -0.65692(11) -0.57184(11) -0.7014(3) 0.0393(6) Uani 1 1 d . . . . .
H4 H -0.634479 -0.584560 -0.788252 0.047 Uiso 1 1 calc R . . . .
C22 C -0.90661(11) -0.73984(11) -0.2976(3) 0.0348(5) Uani 1 1 d . . . . .
H22A H -0.877892 -0.779752 -0.275058 0.052 Uiso 1 1 calc GR . . . .
H22B H -0.955136 -0.752370 -0.287941 0.052 Uiso 1 1 calc GR . . . .
H22C H -0.895870 -0.702393 -0.230759 0.052 Uiso 1 1 calc GR . . . .
C20 C -0.87442(12) -0.88892(11) -0.6407(3) 0.0401(5) Uani 1 1 d . . . . .
H20A H -0.842522 -0.896690 -0.720625 0.060 Uiso 1 1 calc GR . . . .
H20B H -0.921436 -0.886154 -0.677879 0.060 Uiso 1 1 calc GR . . . .
H20C H -0.871056 -0.927011 -0.572090 0.060 Uiso 1 1 calc GR . . . .
C2 C -0.66402(12) -0.50092(11) -0.4933(3) 0.0439(6) Uani 1 1 d . . . . .
H2 H -0.646319 -0.464424 -0.436452 0.053 Uiso 1 1 calc R . . . .
C17 C -0.67517(11) -0.85804(10) -0.4735(3) 0.0343(5) Uani 1 1 d . . . . .
H17 H -0.643341 -0.895001 -0.475586 0.041 Uiso 1 1 calc R . . . .
C9 C -0.89210(11) -0.54129(12) -0.6121(3) 0.0410(6) Uani 1 1 d . . . . .
H9A H -0.858445 -0.503996 -0.605493 0.061 Uiso 1 1 calc GR . . . .
H9B H -0.938594 -0.522075 -0.609437 0.061 Uiso 1 1 calc GR . . . .
H9C H -0.885445 -0.566279 -0.702606 0.061 Uiso 1 1 calc GR . . . .
C18 C -0.74126(11) -0.86836(10) -0.5219(2) 0.0314(5) Uani 1 1 d . . . . .
H18 H -0.754587 -0.912200 -0.557057 0.038 Uiso 1 1 calc R . . . .
C10 C -0.89142(12) -0.55059(12) -0.3450(3) 0.0423(6) Uani 1 1 d . . . . .
H10A H -0.882008 -0.580982 -0.263247 0.064 Uiso 1 1 calc GR . . . .
H10B H -0.938629 -0.533439 -0.338481 0.064 Uiso 1 1 calc GR . . . .
H10C H -0.859380 -0.511787 -0.343188 0.064 Uiso 1 1 calc GR . . . .
C3 C -0.63158(11) -0.51871(11) -0.6191(3) 0.0436(6) Uani 1 1 d . . . . .
H3 H -0.591770 -0.494455 -0.649237 0.052 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 C21 1.224(2) . ?
N1 C19 1.418(2) . ?
N1 C21 1.373(3) . ?
N1 C20 1.463(3) . ?
C6 C7 1.481(3) . ?
C6 C5 1.389(3) . ?
C6 C1 1.392(3) . ?
C14 C13 1.463(2) . ?
C14 C19 1.413(3) . ?
C14 C15 1.388(3) . ?
C7 C13 1.336(3) . ?
C7 C8 1.533(3) . ?
C13 C12 1.508(2) . ?
C5 C4 1.385(3) . ?
C16 C15 1.383(3) . ?
C16 C17 1.377(3) . ?
C19 C18 1.393(3) . ?
C1 C2 1.387(3) . ?
C21 C12 1.521(3) . ?
C11 C8 1.547(3) . ?
C11 C12 1.533(3) . ?
C8 C9 1.529(3) . ?
C8 C10 1.528(3) . ?
C12 C22 1.537(3) . ?
C4 C3 1.378(3) . ?
C2 C3 1.373(4) . ?
C17 C18 1.378(3) . ?

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
C19 N1 C20 118.78(17) . . ?
C21 N1 C19 123.64(16) . . ?
C21 N1 C20 117.58(17) . . ?
C5 C6 C7 118.51(18) . . ?
C5 C6 C1 118.16(18) . . ?
C1 C6 C7 123.28(19) . . ?
C19 C14 C13 117.27(16) . . ?
C15 C14 C13 123.97(17) . . ?
C15 C14 C19 118.74(17) . . ?
C6 C7 C8 121.77(16) . . ?
C13 C7 C6 126.41(16) . . ?
C13 C7 C8 111.57(16) . . ?
C14 C13 C12 116.08(16) . . ?
C7 C13 C14 131.39(17) . . ?
C7 C13 C12 112.51(16) . . ?
C4 C5 C6 121.4(2) . . ?
C17 C16 C15 119.2(2) . . ?
C14 C19 N1 119.73(16) . . ?
C18 C19 N1 120.94(17) . . ?
C18 C19 C14 119.31(18) . . ?
C2 C1 C6 120.3(2) . . ?
O1 C21 N1 121.53(19) . . ?
O1 C21 C12 121.72(19) . . ?
N1 C21 C12 116.67(17) . . ?
C12 C11 C8 107.06(15) . . ?
C16 C15 C14 121.45(19) . . ?
C7 C8 C11 101.76(15) . . ?
C9 C8 C7 111.36(17) . . ?
C9 C8 C11 111.08(18) . . ?
C10 C8 C7 111.80(18) . . ?
C10 C8 C11 111.75(18) . . ?
C10 C8 C9 108.98(17) . . ?
C13 C12 C21 109.98(16) . . ?
C13 C12 C11 102.82(15) . . ?
C13 C12 C22 111.88(17) . . ?
C21 C12 C11 112.41(17) . . ?
C21 C12 C22 106.63(16) . . ?
C11 C12 C22 113.19(16) . . ?
C3 C4 C5 119.7(2) . . ?
C3 C2 C1 120.7(2) . . ?
C16 C17 C18 121.06(18) . . ?
C17 C18 C19 120.21(19) . . ?
C2 C3 C4 119.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
