# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_qizhj_0412
_database_code_depnum_ccdc_archive 'CCDC 2478060'
loop_
_audit_author_name
_audit_author_address
Aa
;jining university
China
;
_audit_update_record             
;
2025-08-03 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_audit_creation_date             2018-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1171(2)
_cell_length_b                   17.9923(6)
_cell_length_c                   7.2098(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.534(4)
_cell_angle_gamma                90.00
_cell_volume                     885.05(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1726
_cell_measurement_temperature    290.89(10)
_cell_measurement_theta_max      69.7380
_cell_measurement_theta_min      6.3930
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3211
_diffrn_reflns_theta_full        69.35
_diffrn_reflns_theta_max         69.35
_diffrn_reflns_theta_min         6.94
_diffrn_ambient_temperature      290.89(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   77.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega  -82.00  -56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -51.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega    3.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   75.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 10 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 63

#__ type_ start__ end____ width___ exp.time_
 12 omega  129.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   50.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
 14 omega  128.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
 15 omega  124.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega   42.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   35.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
 18 omega   81.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
 19 omega   48.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   91.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  120.0000 35
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0142439000
_diffrn_orient_matrix_UB_12      -0.0724394000
_diffrn_orient_matrix_UB_13      0.1171232000
_diffrn_orient_matrix_UB_21      -0.2072562000
_diffrn_orient_matrix_UB_22      -0.0220511000
_diffrn_orient_matrix_UB_23      -0.1226784000
_diffrn_orient_matrix_UB_31      0.0884578000
_diffrn_orient_matrix_UB_32      -0.0399919000
_diffrn_orient_matrix_UB_33      -0.1445532000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1400
_reflns_number_total             1580
_reflns_odcompleteness_completeness 95.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1580
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0737P)²+0.1061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1242
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.8534(2) 0.06182(6) 0.41225(16) 0.0803(4) Uani 1 d . . .
O2 O 0.8636(2) 0.18114(7) 0.4059(2) 0.0914(5) Uani 1 d . . .
N1 N 0.8365(2) 0.12045(6) 0.32420(19) 0.0564(3) Uani 1 d . . .
C1 C 0.73956(16) -0.01105(8) -0.04644(18) 0.0438(3) Uani 1 d . . .
C2 C 0.77963(19) -0.06199(8) 0.1058(2) 0.0513(3) Uani 1 d . . .
H2 H 0.8140 -0.0450 0.2329 0.062 Uiso 1 calc . . R
C3 C 0.7685(2) -0.13739(9) 0.0690(3) 0.0621(4) Uani 1 d . . .
H3 H 0.7948 -0.1709 0.1714 0.074 Uiso 1 calc . . R
C4 C 0.7187(2) -0.16350(9) -0.1191(3) 0.0687(5) Uani 1 d . . .
H4 H 0.7101 -0.2143 -0.1431 0.082 Uiso 1 calc . . R
C5 C 0.6820(3) -0.11429(10) -0.2693(3) 0.0735(5) Uani 1 d . . .
H5 H 0.6499 -0.1319 -0.3958 0.088 Uiso 1 calc . . R
C6 C 0.6921(2) -0.03869(10) -0.2354(2) 0.0607(4) Uani 1 d . . .
H6 H 0.6672 -0.0058 -0.3391 0.073 Uiso 1 calc . . R
C7 C 0.74617(17) 0.06894(8) -0.02084(18) 0.0444(3) Uani 1 d . . .
C8 C 0.7053(3) 0.12917(9) -0.1747(2) 0.0612(4) Uani 1 d . . .
H8A H 0.793(2) 0.1305(9) -0.247(3) 0.061(5) Uiso 1 d . . .
H8B H 0.572(3) 0.1306(9) -0.250(3) 0.070(5) Uiso 1 d . . .
C9 C 0.7507(2) 0.18764(9) -0.0093(3) 0.0627(4) Uani 1 d . . .
H9A H 0.8671 0.2172 0.0010 0.075 Uiso 1 calc . . R
H9B H 0.6399 0.2183 -0.0048 0.075 Uiso 1 calc . . R
C10 C 0.78259(19) 0.12142(7) 0.1191(2) 0.0473(3) Uani 1 d . . .


_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 N1 1.2193(16) . ?
O2 N1 1.2297(16) . ?
N1 C10 1.4182(19) . ?
C1 C2 1.3958(19) . ?
C1 C6 1.3981(19) . ?
C1 C7 1.450(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.365(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.5184(18) . ?
C7 C10 1.3520(19) . ?
C8 H8A 0.919(18) . ?
C8 H8B 0.95(2) . ?
C8 C9 1.554(3) . ?
C8 C10 2.036(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.4859(19) . ?

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
O1 N1 O2 122.68(15) . . ?
O1 N1 C10 120.72(12) . . ?
O2 N1 C10 116.61(13) . . ?
C2 C1 C6 118.11(14) . . ?
C2 C1 C7 124.03(12) . . ?
C6 C1 C7 117.85(13) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.42(14) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.49(16) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.70(15) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.64(16) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.61(16) . . ?
C5 C6 H6 119.7 . . ?
C1 C7 C8 128.53(12) . . ?
C10 C7 C1 141.32(12) . . ?
C10 C7 C8 90.16(12) . . ?
C7 C8 H8A 114.3(10) . . ?
C7 C8 H8B 112.8(11) . . ?
C7 C8 C9 88.16(12) . . ?
C7 C8 C10 41.61(8) . . ?
H8A C8 H8B 114.1(16) . . ?
C9 C8 H8A 113.0(11) . . ?
C9 C8 H8B 111.9(11) . . ?
C9 C8 C10 46.55(8) . . ?
C10 C8 H8A 124.3(11) . . ?
C10 C8 H8B 121.6(12) . . ?
C8 C9 H9A 114.6 . . ?
C8 C9 H9B 114.6 . . ?
H9A C9 H9B 111.7 . . ?
C10 C9 C8 84.07(11) . . ?
C10 C9 H9A 114.6 . . ?
C10 C9 H9B 114.6 . . ?
N1 C10 C8 176.77(11) . . ?
N1 C10 C9 127.39(13) . . ?
C7 C10 N1 134.99(12) . . ?
C7 C10 C8 48.23(8) . . ?
C7 C10 C9 97.61(12) . . ?
C9 C10 C8 49.38(9) . . ?

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 N1 C10 C7 -2.6(3) . . . . ?
O1 N1 C10 C8 178(2) . . . . ?
O1 N1 C10 C9 178.19(14) . . . . ?
O2 N1 C10 C7 177.77(15) . . . . ?
O2 N1 C10 C8 -2(2) . . . . ?
O2 N1 C10 C9 -1.4(2) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C7 C8 C9 -179.56(13) . . . . ?
C1 C7 C8 C10 179.84(17) . . . . ?
C1 C7 C10 N1 0.2(3) . . . . ?
C1 C7 C10 C8 -179.8(2) . . . . ?
C1 C7 C10 C9 179.57(16) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
C2 C1 C7 C8 -179.88(13) . . . . ?
C2 C1 C7 C10 -0.1(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C6 C1 C2 C3 -1.25(19) . . . . ?
C6 C1 C7 C8 0.8(2) . . . . ?
C6 C1 C7 C10 -179.41(16) . . . . ?
C7 C1 C2 C3 179.47(12) . . . . ?
C7 C1 C6 C5 -179.51(14) . . . . ?
C7 C8 C9 C10 -0.55(10) . . . . ?
C7 C8 C10 N1 180(100) . . . . ?
C7 C8 C10 C9 179.18(15) . . . . ?
C8 C7 C10 N1 -179.99(17) . . . . ?
C8 C7 C10 C9 -0.63(12) . . . . ?
C8 C9 C10 N1 -179.95(15) . . . . ?
C8 C9 C10 C7 0.62(11) . . . . ?
C9 C8 C10 N1 1(2) . . . . ?
C9 C8 C10 C7 -179.18(15) . . . . ?
C10 C7 C8 C9 0.60(11) . . . . ?

_olex2_date_sample_data_collection 2018-04-13
_olex2_submission_special_instructions 'No special instructions were received'
