# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.
# 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_220411i_0m
_database_code_depnum_ccdc_archive 'CCDC 2222100'
loop_
_audit_author_name
_audit_author_address
DOA
;Wuhan university
China
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;
_audit_creation_date             2022-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N O3'
_chemical_formula_sum            'C13 H11 N O3'
_chemical_formula_weight         229.23
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.1781(4)
_cell_length_b                   7.8944(2)
_cell_length_c                   20.3248(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.1780(10)
_cell_angle_gamma                90
_cell_volume                     2112.93(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9588
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      64.35
_cell_measurement_theta_min      3.79
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.545
_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            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13530
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         64.797
_diffrn_reflns_theta_min         5.685
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.976
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2366
_reflns_number_total             2663
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.077
_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)+(0.0667P)²+0.7866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1195
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H) groups, All C(H) groups
2. Restrained distances
 O1-H1
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C13(H13), C12(H12), C2(H2), C10(H10), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.79302(6) -0.36750(10) 0.33348(4) 0.0343(2) Uani 1 1 d D . . . .
N1 N 0.53704(7) 0.31271(12) 0.36651(4) 0.0301(2) Uani 1 1 d . . . . .
O3 O 0.30951(8) 0.88408(11) 0.42159(4) 0.0463(3) Uani 1 1 d . . . . .
O2 O 0.63480(6) 0.15477(10) 0.27639(4) 0.0350(2) Uani 1 1 d . . . . .
C3 C 0.73464(7) -0.23543(12) 0.34801(5) 0.0261(2) Uani 1 1 d . . . . .
C4 C 0.69413(8) -0.22850(14) 0.41188(5) 0.0294(2) Uani 1 1 d . . . . .
H4 H 0.706415 -0.317964 0.442417 0.035 Uiso 1 1 calc R . . . .
C5 C 0.63755(8) -0.09192(14) 0.42863(5) 0.0304(2) Uani 1 1 d . . . . .
H5 H 0.611745 -0.086167 0.471582 0.037 Uiso 1 1 calc R . . . .
C6 C 0.61601(7) 0.04223(13) 0.38365(5) 0.0274(2) Uani 1 1 d . . . . .
C7 C 0.55911(8) 0.18169(14) 0.40424(5) 0.0301(2) Uani 1 1 d . . . . .
C8 C 0.47899(7) 0.45722(13) 0.38219(5) 0.0274(2) Uani 1 1 d . . . . .
C13 C 0.48249(8) 0.59556(14) 0.33982(5) 0.0308(2) Uani 1 1 d . . . . .
H13 H 0.524183 0.591245 0.302742 0.037 Uiso 1 1 calc R . . . .
C12 C 0.42570(8) 0.73930(14) 0.35132(5) 0.0315(2) Uani 1 1 d . . . . .
H12 H 0.427366 0.832551 0.321840 0.038 Uiso 1 1 calc R . . . .
C11 C 0.36604(8) 0.74636(13) 0.40643(5) 0.0308(2) Uani 1 1 d . . . . .
C1 C 0.65507(7) 0.03268(13) 0.31875(5) 0.0266(2) Uani 1 1 d . . . . .
C2 C 0.71434(8) -0.10764(13) 0.30256(5) 0.0279(2) Uani 1 1 d . . . . .
H2 H 0.740973 -0.115321 0.259881 0.033 Uiso 1 1 calc R . . . .
C10 C 0.36358(8) 0.60895(14) 0.44911(5) 0.0321(2) Uani 1 1 d . . . . .
H10 H 0.323428 0.614364 0.486892 0.039 Uiso 1 1 calc R . . . .
C9 C 0.41906(8) 0.46466(14) 0.43699(5) 0.0312(2) Uani 1 1 d . . . . .
H9 H 0.416309 0.370622 0.466034 0.037 Uiso 1 1 calc R . . . .
H3 H 0.3132(13) 0.958(2) 0.3878(9) 0.064(5) Uiso 1 1 d . . . . .
H1 H 0.8212(15) -0.360(2) 0.2895(8) 0.081(6) Uiso 1 1 d D . . . .
H7 H 0.5326(10) 0.1822(18) 0.4489(7) 0.040(4) Uiso 1 1 d . . . . .
H1A H 0.5662(12) 0.301(2) 0.3247(8) 0.048 Uiso 1 1 d 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 C3 1.3355(12) . ?
O1 H1 0.982(15) . ?
N1 C7 1.3136(14) . ?
N1 C8 1.4165(13) . ?
N1 H1A 0.950(16) . ?
O3 C11 1.3599(13) . ?
O3 H3 0.905(19) . ?
O2 C1 1.3130(12) . ?
C3 C4 1.4234(13) . ?
C3 C2 1.3870(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.3616(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.4205(14) . ?
C6 C7 1.4048(14) . ?
C6 C1 1.4361(13) . ?
C7 H7 0.984(15) . ?
C8 C13 1.3926(14) . ?
C8 C9 1.3909(13) . ?
C13 H13 0.9500 . ?
C13 C12 1.3841(15) . ?
C12 H12 0.9500 . ?
C12 C11 1.3937(14) . ?
C11 C10 1.3901(15) . ?
C1 C2 1.4018(14) . ?
C2 H2 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.3808(14) . ?
C9 H9 0.9500 . ?

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
C3 O1 H1 113.4(12) . . ?
C7 N1 C8 127.75(9) . . ?
C7 N1 H1A 111.1(10) . . ?
C8 N1 H1A 121.1(10) . . ?
C11 O3 H3 107.4(11) . . ?
O1 C3 C4 118.09(9) . . ?
O1 C3 C2 121.25(9) . . ?
C2 C3 C4 120.66(9) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.10(9) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.83(9) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.83(9) . . ?
C7 C6 C5 119.23(9) . . ?
C7 C6 C1 121.93(9) . . ?
N1 C7 C6 123.51(9) . . ?
N1 C7 H7 117.1(8) . . ?
C6 C7 H7 119.3(8) . . ?
C13 C8 N1 117.49(9) . . ?
C9 C8 N1 122.82(9) . . ?
C9 C8 C13 119.68(9) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.51(9) . . ?
C12 C13 H13 119.7 . . ?
C13 C12 H12 120.2 . . ?
C13 C12 C11 119.58(9) . . ?
C11 C12 H12 120.2 . . ?
O3 C11 C12 123.00(10) . . ?
O3 C11 C10 117.16(9) . . ?
C10 C11 C12 119.84(9) . . ?
O2 C1 C6 119.51(9) . . ?
O2 C1 C2 121.84(9) . . ?
C2 C1 C6 118.65(9) . . ?
C3 C2 C1 120.90(9) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.49(9) . . ?
C9 C10 H10 119.8 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.89(9) . . ?
C10 C9 H9 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 C3 C4 C5 177.57(9) . . . . ?
O1 C3 C2 C1 -178.40(9) . . . . ?
N1 C8 C13 C12 178.42(9) . . . . ?
N1 C8 C9 C10 -179.40(10) . . . . ?
O3 C11 C10 C9 -179.96(10) . . . . ?
O2 C1 C2 C3 -179.85(9) . . . . ?
C3 C4 C5 C6 1.35(16) . . . . ?
C4 C3 C2 C1 1.15(15) . . . . ?
C4 C5 C6 C7 -178.58(10) . . . . ?
C4 C5 C6 C1 0.11(16) . . . . ?
C5 C6 C7 N1 178.78(10) . . . . ?
C5 C6 C1 O2 179.21(9) . . . . ?
C5 C6 C1 C2 -0.96(15) . . . . ?
C6 C1 C2 C3 0.33(15) . . . . ?
C7 N1 C8 C13 167.23(11) . . . . ?
C7 N1 C8 C9 -13.44(17) . . . . ?
C7 C6 C1 O2 -2.13(15) . . . . ?
C7 C6 C1 C2 177.69(9) . . . . ?
C8 N1 C7 C6 178.77(9) . . . . ?
C8 C13 C12 C11 1.16(16) . . . . ?
C13 C8 C9 C10 -0.08(16) . . . . ?
C13 C12 C11 O3 178.91(10) . . . . ?
C13 C12 C11 C10 -0.37(16) . . . . ?
C12 C11 C10 C9 -0.64(17) . . . . ?
C11 C10 C9 C8 0.86(17) . . . . ?
C1 C6 C7 N1 0.13(17) . . . . ?
C2 C3 C4 C5 -1.99(15) . . . . ?
C9 C8 C13 C12 -0.93(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
