# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ycs20230524shi2_0m
_database_code_depnum_ccdc_archive 'CCDC 2272265'
loop_
_audit_author_name
_audit_author_address
'Kai zhangkai'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.36

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                   9.941(3)
_cell_length_b                   15.496(4)
_cell_length_c                   10.942(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.198(3)
_cell_angle_gamma                90
_cell_volume                     1678.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    10361
_cell_measurement_theta_min      4.585
_cell_measurement_theta_max      57.276

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10118
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.629
_diffrn_reflns_theta_max         28.844
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4000
_reflns_number_gt                2966
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0622P)²+0.4105P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4000
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.59418(14) 0.31302(10) 0.59059(14) 0.0766(4) Uani 1 1 d . . . . .
O2 O 0.91488(12) 0.35075(9) 0.28963(12) 0.0651(4) Uani 1 1 d . . . . .
N1 N 0.75779(13) 0.39447(9) 0.42474(12) 0.0469(3) Uani 1 1 d . . . . .
C1 C 0.7643(2) 0.33387(13) 0.75004(18) 0.0689(5) Uani 1 1 d . . . . .
H1 H 0.705901 0.311599 0.803841 0.083 Uiso 1 1 calc R U . . .
C2 C 0.8946(2) 0.35430(14) 0.79191(18) 0.0727(6) Uani 1 1 d . . . . .
H2 H 0.924292 0.345310 0.873974 0.087 Uiso 1 1 calc R U . . .
C3 C 0.9814(2) 0.38787(13) 0.71374(19) 0.0690(5) Uani 1 1 d . . . . .
H3 H 1.069838 0.401153 0.742482 0.083 Uiso 1 1 calc R U . . .
C4 C 0.93669(18) 0.40189(11) 0.59198(17) 0.0565(4) Uani 1 1 d . . . . .
H4 H 0.995188 0.425299 0.539141 0.068 Uiso 1 1 calc R U . . .
C5 C 0.80555(16) 0.38135(10) 0.54808(14) 0.0452(3) Uani 1 1 d . . . . .
C6 C 0.71940(17) 0.34641(10) 0.62727(15) 0.0508(4) Uani 1 1 d . . . . .
C7 C 0.49120(17) 0.34634(10) 0.51054(15) 0.0486(4) Uani 1 1 d . . . . .
C8 C 0.36529(18) 0.31579(11) 0.53662(17) 0.0563(4) Uani 1 1 d . . . . .
H8 H 0.358881 0.278787 0.602751 0.068 Uiso 1 1 calc R U . . .
C9 C 0.25081(18) 0.33972(12) 0.46580(18) 0.0614(5) Uani 1 1 d . . . . .
H9 H 0.167333 0.318093 0.483047 0.074 Uiso 1 1 calc R U . . .
C10 C 0.63341(15) 0.43684(9) 0.37348(13) 0.0415(3) Uani 1 1 d . . . . .
H10 H 0.638345 0.499152 0.388565 0.050 Uiso 1 1 calc R U . . .
C11 C 0.25898(18) 0.39585(13) 0.36886(19) 0.0632(5) Uani 1 1 d . . . . .
H11 H 0.181264 0.413263 0.321575 0.076 Uiso 1 1 calc R U . . .
C12 C 0.38400(17) 0.42581(11) 0.34304(16) 0.0545(4) Uani 1 1 d . . . . .
H12 H 0.389024 0.463861 0.277873 0.065 Uiso 1 1 calc R U . . .
C13 C 0.50322(15) 0.40105(9) 0.41123(14) 0.0438(3) Uani 1 1 d . . . . .
C14 C 0.67965(15) 0.41503(9) 0.24258(13) 0.0421(3) Uani 1 1 d . . . . .
C15 C 0.60238(19) 0.34134(11) 0.17541(17) 0.0581(4) Uani 1 1 d . . . . .
H15A H 0.592822 0.294472 0.231348 0.087 Uiso 1 1 calc R U . . .
H15B H 0.651141 0.321931 0.108751 0.087 Uiso 1 1 calc R U . . .
H15C H 0.514583 0.361295 0.143912 0.087 Uiso 1 1 calc R U . . .
C16 C 0.80899(16) 0.38078(10) 0.31493(14) 0.0460(4) Uani 1 1 d . . . . .
C17 C 0.70151(16) 0.49022(10) 0.15856(13) 0.0463(4) Uani 1 1 d . . . . .
C18 C 0.6367(2) 0.56878(11) 0.16595(16) 0.0571(4) Uani 1 1 d . . . . .
H18 H 0.575344 0.576792 0.224252 0.069 Uiso 1 1 calc R U . . .
C19 C 0.6624(3) 0.63585(13) 0.08704(19) 0.0745(6) Uani 1 1 d . . . . .
H19 H 0.619460 0.688752 0.093486 0.089 Uiso 1 1 calc R U . . .
C20 C 0.7512(3) 0.62394(16) -0.0004(2) 0.0833(7) Uani 1 1 d . . . . .
H20 H 0.768206 0.668778 -0.053350 0.100 Uiso 1 1 calc R U . . .
C21 C 0.8149(2) 0.54630(17) -0.00980(19) 0.0792(6) Uani 1 1 d . . . . .
H21 H 0.874507 0.538357 -0.069602 0.095 Uiso 1 1 calc R U . . .
C22 C 0.7910(2) 0.47979(13) 0.06899(16) 0.0634(5) Uani 1 1 d . . . . .
H22 H 0.835174 0.427339 0.062212 0.076 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 C6 1.374(2) . ?
O1 C7 1.385(2) . ?
O2 C16 1.2059(18) . ?
N1 C16 1.3633(19) . ?
N1 C5 1.404(2) . ?
N1 C10 1.4659(19) . ?
C1 C2 1.371(3) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C7 C8 1.392(2) . ?
C7 C13 1.392(2) . ?
C8 C9 1.369(3) . ?
C8 H8 0.9300 . ?
C9 C11 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C13 1.500(2) . ?
C10 C14 1.5800(19) . ?
C10 H10 0.9800 . ?
C11 C12 1.380(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.396(2) . ?
C12 H12 0.9300 . ?
C14 C17 1.512(2) . ?
C14 C15 1.527(2) . ?
C14 C16 1.542(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 C18 1.383(2) . ?
C17 C22 1.391(2) . ?
C18 C19 1.390(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(3) . ?
C21 H21 0.9300 . ?
C22 H22 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
C6 O1 C7 129.97(13) . . ?
C16 N1 C5 134.73(14) . . ?
C16 N1 C10 95.84(12) . . ?
C5 N1 C10 129.24(12) . . ?
C2 C1 C6 120.11(18) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 120.51(18) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 119.69(19) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.53(17) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.32(15) . . ?
C6 C5 N1 118.96(15) . . ?
C4 C5 N1 121.71(14) . . ?
O1 C6 C5 124.10(15) . . ?
O1 C6 C1 115.65(16) . . ?
C5 C6 C1 119.82(17) . . ?
O1 C7 C8 111.74(15) . . ?
O1 C7 C13 127.58(14) . . ?
C8 C7 C13 120.64(16) . . ?
C9 C8 C7 120.59(17) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C11 120.14(16) . . ?
C8 C9 H9 119.9 . . ?
C11 C9 H9 119.9 . . ?
N1 C10 C13 116.61(12) . . ?
N1 C10 C14 86.93(10) . . ?
C13 C10 C14 119.98(12) . . ?
N1 C10 H10 110.4 . . ?
C13 C10 H10 110.4 . . ?
C14 C10 H10 110.4 . . ?
C12 C11 C9 119.10(18) . . ?
C12 C11 H11 120.4 . . ?
C9 C11 H11 120.4 . . ?
C11 C12 C13 122.34(17) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C7 C13 C12 117.13(15) . . ?
C7 C13 C10 125.27(14) . . ?
C12 C13 C10 117.58(14) . . ?
C17 C14 C15 112.16(13) . . ?
C17 C14 C16 114.73(13) . . ?
C15 C14 C16 110.46(13) . . ?
C17 C14 C10 117.13(12) . . ?
C15 C14 C10 114.92(12) . . ?
C16 C14 C10 84.60(11) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 N1 131.74(16) . . ?
O2 C16 C14 136.03(15) . . ?
N1 C16 C14 92.20(11) . . ?
C18 C17 C22 118.31(16) . . ?
C18 C17 C14 123.32(14) . . ?
C22 C17 C14 118.37(15) . . ?
C17 C18 C19 120.60(18) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.16(19) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.7(2) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?

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
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 N1 -179.65(16) . . . . ?
C16 N1 C5 C6 -136.72(18) . . . . ?
C10 N1 C5 C6 49.5(2) . . . . ?
C16 N1 C5 C4 42.8(3) . . . . ?
C10 N1 C5 C4 -130.98(17) . . . . ?
C7 O1 C6 C5 -46.4(3) . . . . ?
C7 O1 C6 C1 141.29(18) . . . . ?
C4 C5 C6 O1 -170.83(16) . . . . ?
N1 C5 C6 O1 8.7(2) . . . . ?
C4 C5 C6 C1 1.2(2) . . . . ?
N1 C5 C6 C1 -179.24(15) . . . . ?
C2 C1 C6 O1 171.26(18) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
C6 O1 C7 C8 -153.69(18) . . . . ?
C6 O1 C7 C13 28.7(3) . . . . ?
O1 C7 C8 C9 -178.45(16) . . . . ?
C13 C7 C8 C9 -0.7(2) . . . . ?
C7 C8 C9 C11 -1.2(3) . . . . ?
C16 N1 C10 C13 127.37(13) . . . . ?
C5 N1 C10 C13 -57.1(2) . . . . ?
C16 N1 C10 C14 5.18(12) . . . . ?
C5 N1 C10 C14 -179.26(15) . . . . ?
C8 C9 C11 C12 1.4(3) . . . . ?
C9 C11 C12 C13 0.3(3) . . . . ?
O1 C7 C13 C12 179.65(16) . . . . ?
C8 C7 C13 C12 2.3(2) . . . . ?
O1 C7 C13 C10 -1.7(3) . . . . ?
C8 C7 C13 C10 -179.10(14) . . . . ?
C11 C12 C13 C7 -2.1(2) . . . . ?
C11 C12 C13 C10 179.15(15) . . . . ?
N1 C10 C13 C7 16.2(2) . . . . ?
C14 C10 C13 C7 118.87(17) . . . . ?
N1 C10 C13 C12 -165.19(13) . . . . ?
C14 C10 C13 C12 -62.50(19) . . . . ?
N1 C10 C14 C17 -119.64(14) . . . . ?
C13 C10 C14 C17 121.22(15) . . . . ?
N1 C10 C14 C15 105.49(14) . . . . ?
C13 C10 C14 C15 -13.6(2) . . . . ?
N1 C10 C14 C16 -4.58(10) . . . . ?
C13 C10 C14 C16 -123.71(14) . . . . ?
C5 N1 C16 O2 1.3(3) . . . . ?
C10 N1 C16 O2 176.43(18) . . . . ?
C5 N1 C16 C14 179.53(17) . . . . ?
C10 N1 C16 C14 -5.30(12) . . . . ?
C17 C14 C16 O2 -59.5(2) . . . . ?
C15 C14 C16 O2 68.4(2) . . . . ?
C10 C14 C16 O2 -177.0(2) . . . . ?
C17 C14 C16 N1 122.35(13) . . . . ?
C15 C14 C16 N1 -109.69(13) . . . . ?
C10 C14 C16 N1 4.92(11) . . . . ?
C15 C14 C17 C18 109.82(18) . . . . ?
C16 C14 C17 C18 -123.09(17) . . . . ?
C10 C14 C17 C18 -26.2(2) . . . . ?
C15 C14 C17 C22 -69.96(19) . . . . ?
C16 C14 C17 C22 57.13(19) . . . . ?
C10 C14 C17 C22 154.00(15) . . . . ?
C22 C17 C18 C19 -1.1(3) . . . . ?
C14 C17 C18 C19 179.15(16) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C17 0.4(3) . . . . ?
C18 C17 C22 C21 0.4(3) . . . . ?
C14 C17 C22 C21 -179.84(18) . . . . ?

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036

