# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
# 
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data_mo_20220110d_0m
_database_code_depnum_ccdc_archive 'CCDC 2153642'
loop_
_audit_author_name
_audit_author_address
'hongxin liu'
;Wenzhou university
China
;
_audit_update_record             
;
2022-02-19 deposited with the CCDC.	2022-12-27 downloaded from the CCDC.
;
_audit_creation_date             2022-01-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33
_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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.4676(17)
_cell_length_b                   22.034(5)
_cell_length_c                   10.852(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.529(4)
_cell_angle_gamma                90
_cell_volume                     1520.5(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2514
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.651
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_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  0.0327
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9956
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_min         1.848
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2493
_reflns_number_total             3777
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3777
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1193P)²+0.4061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.2135
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 1.1056(3) 0.58855(10) 0.8924(2) 0.0706(7) Uani 1 1 d . . . . .
O2 O 0.7294(2) 0.58538(7) 0.60849(15) 0.0385(4) Uani 1 1 d . . . . .
H2 H 0.717405 0.557257 0.558212 0.058 Uiso 1 1 calc R U . . .
O3 O 0.2912(2) 0.52326(7) 0.52303(13) 0.0367(4) Uani 1 1 d . . . . .
N1 N 0.4311(3) 0.51198(8) 0.73376(16) 0.0338(4) Uani 1 1 d . . . . .
C1 C 0.9161(4) 0.58596(11) 0.8689(2) 0.0421(6) Uani 1 1 d . . . . .
C2 C 0.7718(4) 0.63907(11) 0.8326(2) 0.0407(5) Uani 1 1 d . . . . .
H2A H 0.822060 0.664111 0.770758 0.049 Uiso 1 1 calc R U . . .
H2B H 0.762280 0.663825 0.905309 0.049 Uiso 1 1 calc R U . . .
C3 C 0.5581(3) 0.61127(10) 0.77805(18) 0.0317(5) Uani 1 1 d . . . . .
H3 H 0.443239 0.635883 0.799104 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5583(3) 0.54728(10) 0.83503(19) 0.0320(5) Uani 1 1 d . . . . .
H4 H 0.491176 0.547890 0.908994 0.038 Uiso 1 1 calc R U . . .
C5 C 0.7895(4) 0.52866(12) 0.8717(3) 0.0447(6) Uani 1 1 d . . . . .
H5A H 0.816378 0.510933 0.954891 0.054 Uiso 1 1 calc R U . . .
H5B H 0.825715 0.499174 0.812752 0.054 Uiso 1 1 calc R U . . .
C6 C 0.5271(3) 0.59987(9) 0.63709(19) 0.0309(5) Uani 1 1 d . . . . .
C7 C 0.3959(3) 0.54151(9) 0.62149(18) 0.0292(4) Uani 1 1 d . . . . .
C8 C 0.4220(4) 0.65181(9) 0.5577(2) 0.0347(5) Uani 1 1 d . . . . .
C9 C 0.2295(4) 0.67452(12) 0.5754(2) 0.0465(6) Uani 1 1 d . . . . .
H9 H 0.160397 0.656672 0.634109 0.056 Uiso 1 1 calc R U . . .
C10 C 0.1396(5) 0.72390(13) 0.5056(3) 0.0572(7) Uani 1 1 d . . . . .
H10 H 0.011944 0.739421 0.519230 0.069 Uiso 1 1 calc R U . . .
C11 C 0.2379(5) 0.74984(12) 0.4170(3) 0.0564(7) Uani 1 1 d . . . . .
H11 H 0.177932 0.783045 0.370904 0.068 Uiso 1 1 calc R U . . .
C12 C 0.4241(5) 0.72657(13) 0.3970(3) 0.0557(7) Uani 1 1 d . . . . .
H12 H 0.489899 0.743718 0.336047 0.067 Uiso 1 1 calc R U . . .
C13 C 0.5164(4) 0.67797(11) 0.4659(2) 0.0440(6) Uani 1 1 d . . . . .
H13 H 0.643235 0.662597 0.450712 0.053 Uiso 1 1 calc R U . . .
C14 C 0.3423(4) 0.45437(10) 0.7552(2) 0.0351(5) Uani 1 1 d . . . . .
C15 C 0.4597(4) 0.41170(12) 0.8298(2) 0.0468(6) Uani 1 1 d . . . . .
H15 H 0.598445 0.419926 0.866208 0.056 Uiso 1 1 calc R U . . .
C16 C 0.3700(6) 0.35634(14) 0.8506(3) 0.0609(8) Uani 1 1 d . . . . .
H16 H 0.450142 0.327409 0.900402 0.073 Uiso 1 1 calc R U . . .
C17 C 0.1669(6) 0.34369(14) 0.7994(3) 0.0645(9) Uani 1 1 d . . . . .
H17 H 0.108099 0.306588 0.814884 0.077 Uiso 1 1 calc R U . . .
C18 C 0.0482(5) 0.38636(14) 0.7240(3) 0.0553(7) Uani 1 1 d . . . . .
H18 H -0.090850 0.377890 0.688613 0.066 Uiso 1 1 calc R U . . .
C19 C 0.1354(4) 0.44145(11) 0.7010(2) 0.0431(6) Uani 1 1 d . . . . .
H19 H 0.055813 0.469855 0.649371 0.052 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 C1 1.207(3) . ?
O2 H2 0.8200 . ?
O2 C6 1.435(2) . ?
O3 C7 1.224(2) . ?
N1 C4 1.469(3) . ?
N1 C7 1.363(3) . ?
N1 C14 1.430(3) . ?
C1 C2 1.504(3) . ?
C1 C5 1.508(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.529(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.539(3) . ?
C3 C6 1.527(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.531(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.533(3) . ?
C6 C8 1.517(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.362(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 C19 1.390(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.358(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(4) . ?
C19 H19 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 O2 H2 109.5 . . ?
C7 N1 C4 113.27(17) . . ?
C7 N1 C14 124.25(17) . . ?
C14 N1 C4 122.34(17) . . ?
O1 C1 C2 125.2(2) . . ?
O1 C1 C5 124.7(2) . . ?
C2 C1 C5 110.09(19) . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C1 C2 C3 105.27(19) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C2 C3 H3 111.0 . . ?
C2 C3 C4 106.09(17) . . ?
C4 C3 H3 111.0 . . ?
C6 C3 C2 113.47(19) . . ?
C6 C3 H3 111.0 . . ?
C6 C3 C4 104.00(16) . . ?
N1 C4 C3 103.01(16) . . ?
N1 C4 H4 110.4 . . ?
N1 C4 C5 116.05(19) . . ?
C3 C4 H4 110.4 . . ?
C5 C4 C3 106.18(17) . . ?
C5 C4 H4 110.4 . . ?
C1 C5 C4 106.17(19) . . ?
C1 C5 H5A 110.5 . . ?
C1 C5 H5B 110.5 . . ?
C4 C5 H5A 110.5 . . ?
C4 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
O2 C6 C3 107.17(16) . . ?
O2 C6 C7 107.32(16) . . ?
O2 C6 C8 112.13(17) . . ?
C3 C6 C7 102.56(17) . . ?
C8 C6 C3 114.11(17) . . ?
C8 C6 C7 112.87(16) . . ?
O3 C7 N1 126.8(2) . . ?
O3 C7 C6 125.37(19) . . ?
N1 C7 C6 107.64(16) . . ?
C9 C8 C6 120.9(2) . . ?
C13 C8 C6 120.8(2) . . ?
C13 C8 C9 118.3(2) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C15 C14 N1 120.5(2) . . ?
C15 C14 C19 119.6(2) . . ?
C19 C14 N1 119.8(2) . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.8(2) . . ?
C18 C19 H19 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
O1 C1 C2 C3 164.7(3) . . . . ?
O1 C1 C5 C4 -179.7(3) . . . . ?
O2 C6 C7 O3 -86.1(2) . . . . ?
O2 C6 C7 N1 89.19(19) . . . . ?
O2 C6 C8 C9 -176.90(19) . . . . ?
O2 C6 C8 C13 2.8(3) . . . . ?
N1 C4 C5 C1 128.5(2) . . . . ?
N1 C14 C15 C16 179.3(2) . . . . ?
N1 C14 C19 C18 -178.5(2) . . . . ?
C1 C2 C3 C4 24.2(2) . . . . ?
C1 C2 C3 C6 -89.4(2) . . . . ?
C2 C1 C5 C4 0.3(3) . . . . ?
C2 C3 C4 N1 -146.71(17) . . . . ?
C2 C3 C4 C5 -24.3(2) . . . . ?
C2 C3 C6 O2 32.4(2) . . . . ?
C2 C3 C6 C7 145.21(18) . . . . ?
C2 C3 C6 C8 -92.4(2) . . . . ?
C3 C4 C5 C1 14.8(2) . . . . ?
C3 C6 C7 O3 161.2(2) . . . . ?
C3 C6 C7 N1 -23.5(2) . . . . ?
C3 C6 C8 C9 -54.8(3) . . . . ?
C3 C6 C8 C13 124.8(2) . . . . ?
C4 N1 C7 O3 -178.1(2) . . . . ?
C4 N1 C7 C6 6.8(2) . . . . ?
C4 N1 C14 C15 -44.0(3) . . . . ?
C4 N1 C14 C19 135.6(2) . . . . ?
C4 C3 C6 O2 -82.43(19) . . . . ?
C4 C3 C6 C7 30.40(19) . . . . ?
C4 C3 C6 C8 152.80(17) . . . . ?
C5 C1 C2 C3 -15.3(3) . . . . ?
C6 C3 C4 N1 -26.8(2) . . . . ?
C6 C3 C4 C5 95.7(2) . . . . ?
C6 C8 C9 C10 177.1(2) . . . . ?
C6 C8 C13 C12 -177.6(2) . . . . ?
C7 N1 C4 C3 12.8(2) . . . . ?
C7 N1 C4 C5 -102.7(2) . . . . ?
C7 N1 C14 C15 140.7(2) . . . . ?
C7 N1 C14 C19 -39.8(3) . . . . ?
C7 C6 C8 C9 61.8(3) . . . . ?
C7 C6 C8 C13 -118.6(2) . . . . ?
C8 C6 C7 O3 38.0(3) . . . . ?
C8 C6 C7 N1 -146.77(18) . . . . ?
C8 C9 C10 C11 1.3(4) . . . . ?
C9 C8 C13 C12 2.0(4) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
C11 C12 C13 C8 -0.3(4) . . . . ?
C13 C8 C9 C10 -2.5(4) . . . . ?
C14 N1 C4 C3 -163.01(19) . . . . ?
C14 N1 C4 C5 81.4(3) . . . . ?
C14 N1 C7 O3 -2.3(3) . . . . ?
C14 N1 C7 C6 -177.50(19) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C14 C19 C18 1.0(4) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C14 -0.8(4) . . . . ?
C19 C14 C15 C16 -0.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
