# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2264045'
loop_
_audit_author_name
_audit_author_address
'Suosuo Qi'
;zhejiang university of technology
China
;
_audit_update_record             
;
2023-05-19 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;
_audit_creation_date             2023-05-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 N O2'
_chemical_formula_sum            'C22 H19 N O2'
_chemical_formula_weight         329.38
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   12.8035(3)
_cell_length_b                   7.4389(2)
_cell_length_c                   33.9834(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3236.71(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      59.68
_cell_measurement_theta_min      3.76
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0981 before and 0.0508 after correction.
The Ratio of minimum to maximum transmission is 0.8913.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            23768
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.294
_diffrn_reflns_theta_min         3.761
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   MetalJet
_diffrn_source_current           2.86
_diffrn_source_power             0.19931339999999997
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.69
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2779
_reflns_number_total             3573
_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 (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3573
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.028
_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)+(0.0734P)²+0.7834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1326
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C14(H14A,H14B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C9(H9), C20(H20), C3(H3), C10(H10), C5(H5), C2(H2),
 C12(H12), C6(H6), C19(H19)
;
_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
O2 O 0.33910(10) 0.72459(18) 0.49366(4) 0.0624(4) Uani 1 1 d . . . . .
O1 O 0.36462(11) 0.5150(2) 0.45039(4) 0.0686(4) Uani 1 1 d . . . . .
C8 C 0.50973(10) -0.05330(18) 0.60924(4) 0.0326(3) Uani 1 1 d . . . . .
N1 N 0.35701(10) 0.5674(2) 0.48451(4) 0.0486(4) Uani 1 1 d . . . . .
C7 C 0.41837(10) 0.05198(18) 0.60752(4) 0.0320(3) Uani 1 1 d . . . . .
C15 C 0.48664(11) 0.16304(19) 0.71558(4) 0.0334(3) Uani 1 1 d . . . . .
C16 C 0.48480(11) 0.29587(18) 0.68669(4) 0.0338(3) Uani 1 1 d . . . . .
H16 H 0.431730 0.385087 0.687224 0.041 Uiso 1 1 calc R U . . .
C4 C 0.40125(10) 0.18580(19) 0.57577(4) 0.0325(3) Uani 1 1 d . . . . .
C17 C 0.55942(11) 0.29939(18) 0.65721(4) 0.0334(3) Uani 1 1 d . . . . .
H17 H 0.557786 0.392342 0.638055 0.040 Uiso 1 1 calc R U . . .
C18 C 0.63688(10) 0.16814(18) 0.65533(4) 0.0338(3) Uani 1 1 d . . . . .
C9 C 0.51272(12) -0.18929(19) 0.63754(4) 0.0394(3) Uani 1 1 d . . . . .
H9 H 0.565328 -0.279027 0.635889 0.047 Uiso 1 1 calc R U . . .
C20 C 0.57708(11) 0.0610(2) 0.71840(4) 0.0378(3) Uani 1 1 d . . . . .
H20 H 0.588296 -0.011228 0.741062 0.045 Uiso 1 1 calc R U . . .
C3 C 0.41360(11) 0.1376(2) 0.53617(4) 0.0379(3) Uani 1 1 d . . . . .
H3 H 0.431945 0.017460 0.529675 0.045 Uiso 1 1 calc R U . . .
C10 C 0.44095(12) -0.19657(19) 0.66793(5) 0.0417(4) Uani 1 1 d . . . . .
H10 H 0.444476 -0.291197 0.686656 0.050 Uiso 1 1 calc R U . . .
C5 C 0.37171(11) 0.3630(2) 0.58413(4) 0.0374(3) Uani 1 1 d . . . . .
H5 H 0.361304 0.397696 0.610748 0.045 Uiso 1 1 calc R U . . .
C2 C 0.39955(11) 0.2616(2) 0.50651(4) 0.0422(4) Uani 1 1 d . . . . .
H2 H 0.408552 0.227826 0.479768 0.051 Uiso 1 1 calc R U . . .
C11 C 0.36373(11) -0.06618(19) 0.67120(4) 0.0377(3) Uani 1 1 d . . . . .
C21 C 0.68485(11) 0.1186(2) 0.61625(4) 0.0426(4) Uani 1 1 d . . . . .
H21A H 0.750488 0.051723 0.621048 0.051 Uiso 1 1 calc R U . . .
H21B H 0.702920 0.230198 0.601917 0.051 Uiso 1 1 calc R U . . .
C12 C 0.34739(10) 0.04434(19) 0.63888(4) 0.0349(3) Uani 1 1 d . . . . .
H12 H 0.286370 0.116875 0.637988 0.042 Uiso 1 1 calc R U . . .
C22 C 0.61094(11) 0.0002(2) 0.58941(4) 0.0360(3) Uani 1 1 d . . . . .
H22A H 0.594471 0.068230 0.565152 0.043 Uiso 1 1 calc R U . . .
H22B H 0.648918 -0.110065 0.581555 0.043 Uiso 1 1 calc R U . . .
C1 C 0.37216(11) 0.4361(2) 0.51622(4) 0.0387(4) Uani 1 1 d . . . . .
C6 C 0.35731(11) 0.4887(2) 0.55474(4) 0.0401(4) Uani 1 1 d . . . . .
H6 H 0.337651 0.608630 0.560894 0.048 Uiso 1 1 calc R U . . .
C19 C 0.65148(11) 0.0626(2) 0.68865(4) 0.0386(3) Uani 1 1 d . . . . .
H19 H 0.712676 -0.008725 0.691085 0.046 Uiso 1 1 calc R U . . .
C14 C 0.38798(12) 0.1052(2) 0.73650(4) 0.0417(4) Uani 1 1 d . . . . .
H14A H 0.347368 0.213439 0.743771 0.050 Uiso 1 1 calc R U . . .
H14B H 0.407182 0.042121 0.761111 0.050 Uiso 1 1 calc R U . . .
C13 C 0.31715(13) -0.0220(2) 0.71096(5) 0.0459(4) Uani 1 1 d . . . . .
H13A H 0.305265 -0.135310 0.725577 0.055 Uiso 1 1 calc R U . . .
H13B H 0.248444 0.036274 0.706996 0.055 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
O2 N1 1.231(2) . ?
O1 N1 1.2270(18) . ?
C8 C7 1.4088(19) . ?
C8 C9 1.396(2) . ?
C8 C22 1.5140(19) . ?
N1 C1 1.468(2) . ?
C7 C4 1.484(2) . ?
C7 C12 1.4018(19) . ?
C15 C16 1.3932(19) . ?
C15 C20 1.388(2) . ?
C15 C14 1.512(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(2) . ?
C4 C3 1.4015(19) . ?
C4 C5 1.401(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(2) . ?
C18 C21 1.509(2) . ?
C18 C19 1.390(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.378(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.384(2) . ?
C11 C12 1.388(2) . ?
C11 C13 1.513(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.582(2) . ?
C12 H12 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C1 C6 1.379(2) . ?
C6 H6 0.9500 . ?
C19 H19 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.572(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
C7 C8 C22 123.10(12) . . ?
C9 C8 C7 117.01(13) . . ?
C9 C8 C22 118.27(12) . . ?
O2 N1 C1 118.11(14) . . ?
O1 N1 O2 123.74(15) . . ?
O1 N1 C1 118.14(15) . . ?
C8 C7 C4 121.71(12) . . ?
C12 C7 C8 118.96(13) . . ?
C12 C7 C4 118.95(12) . . ?
C16 C15 C14 121.27(13) . . ?
C20 C15 C16 116.78(13) . . ?
C20 C15 C14 120.59(13) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.77(13) . . ?
C17 C16 H16 119.6 . . ?
C3 C4 C7 120.64(13) . . ?
C5 C4 C7 121.58(12) . . ?
C5 C4 C3 117.78(13) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.74(13) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C21 120.09(13) . . ?
C19 C18 C17 117.00(13) . . ?
C19 C18 C21 121.61(13) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.62(13) . . ?
C10 C9 H9 119.2 . . ?
C15 C20 H20 119.4 . . ?
C15 C20 C19 121.15(13) . . ?
C19 C20 H20 119.4 . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 121.07(14) . . ?
C2 C3 H3 119.5 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.34(14) . . ?
C11 C10 H10 119.8 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.80(13) . . ?
C6 C5 H5 119.1 . . ?
C3 C2 H2 120.5 . . ?
C3 C2 C1 119.10(14) . . ?
C1 C2 H2 120.5 . . ?
C10 C11 C13 120.23(14) . . ?
C12 C11 C10 117.22(13) . . ?
C12 C11 C13 121.25(14) . . ?
C18 C21 H21A 108.9 . . ?
C18 C21 H21B 108.9 . . ?
C18 C21 C22 113.58(11) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C7 C12 H12 119.1 . . ?
C11 C12 C7 121.87(13) . . ?
C11 C12 H12 119.1 . . ?
C8 C22 C21 113.68(11) . . ?
C8 C22 H22A 108.8 . . ?
C8 C22 H22B 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C2 C1 N1 118.85(14) . . ?
C6 C1 N1 119.31(14) . . ?
C6 C1 C2 121.83(14) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 C5 118.40(14) . . ?
C1 C6 H6 120.8 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.36(13) . . ?
C20 C19 H19 119.8 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C15 C14 C13 113.19(12) . . ?
H14A C14 H14B 107.8 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C11 C13 C14 113.35(12) . . ?
C11 C13 H13A 108.9 . . ?
C11 C13 H13B 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?

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
O2 N1 C1 C2 -175.54(14) . . . . ?
O2 N1 C1 C6 5.4(2) . . . . ?
O1 N1 C1 C2 3.3(2) . . . . ?
O1 N1 C1 C6 -175.78(14) . . . . ?
C8 C7 C4 C3 50.67(18) . . . . ?
C8 C7 C4 C5 -129.78(14) . . . . ?
C8 C7 C12 C11 -1.12(19) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
N1 C1 C6 C5 179.84(12) . . . . ?
C7 C8 C9 C10 -13.8(2) . . . . ?
C7 C8 C22 C21 89.39(16) . . . . ?
C7 C4 C3 C2 -178.92(13) . . . . ?
C7 C4 C5 C6 178.95(13) . . . . ?
C15 C16 C17 C18 1.2(2) . . . . ?
C15 C20 C19 C18 0.4(2) . . . . ?
C15 C14 C13 C11 2.04(19) . . . . ?
C16 C15 C20 C19 -14.2(2) . . . . ?
C16 C15 C14 C13 77.03(17) . . . . ?
C16 C17 C18 C21 152.03(13) . . . . ?
C16 C17 C18 C19 -15.16(19) . . . . ?
C4 C7 C12 C11 -174.16(12) . . . . ?
C4 C3 C2 C1 -0.4(2) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C17 C18 C21 C22 -74.67(17) . . . . ?
C17 C18 C19 C20 14.3(2) . . . . ?
C18 C21 C22 C8 -4.58(18) . . . . ?
C9 C8 C7 C4 -172.76(12) . . . . ?
C9 C8 C7 C12 14.40(18) . . . . ?
C9 C8 C22 C21 -75.62(16) . . . . ?
C9 C10 C11 C12 13.9(2) . . . . ?
C9 C10 C11 C13 -153.22(14) . . . . ?
C20 C15 C16 C17 13.43(19) . . . . ?
C20 C15 C14 C13 -89.26(17) . . . . ?
C3 C4 C5 C6 -1.5(2) . . . . ?
C3 C2 C1 N1 -179.82(13) . . . . ?
C3 C2 C1 C6 -0.8(2) . . . . ?
C10 C11 C12 C7 -13.2(2) . . . . ?
C10 C11 C13 C14 79.42(18) . . . . ?
C5 C4 C3 C2 1.5(2) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C21 C18 C19 C20 -152.63(14) . . . . ?
C12 C7 C4 C3 -136.49(14) . . . . ?
C12 C7 C4 C5 43.06(18) . . . . ?
C12 C11 C13 C14 -87.21(17) . . . . ?
C22 C8 C7 C4 22.06(19) . . . . ?
C22 C8 C7 C12 -150.78(13) . . . . ?
C22 C8 C9 C10 152.12(14) . . . . ?
C19 C18 C21 C22 91.91(17) . . . . ?
C14 C15 C16 C17 -153.36(13) . . . . ?
C14 C15 C20 C19 152.64(14) . . . . ?
C13 C11 C12 C7 153.87(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
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