# 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_cxx-0429-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2450746'
loop_
_audit_author_name
_audit_author_address
'Xiao Zhang'
;Fujian Normal University
China
;
_audit_update_record             
;
2025-05-13 deposited with the CCDC.	2025-06-09 downloaded from the CCDC.
;
_audit_creation_date             2025-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N O2'
_chemical_formula_sum            'C13 H13 N O2'
_chemical_formula_weight         215.24
_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'

_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                   11.5980(4)
_cell_length_b                   6.6697(2)
_cell_length_c                   14.8861(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.902(3)
_cell_angle_gamma                90
_cell_volume                     1130.73(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5163
_cell_measurement_temperature    298.81(10)
_cell_measurement_theta_max      75.4060
_cell_measurement_theta_min      3.8500
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.846
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6234
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.485
_diffrn_reflns_theta_min         3.881
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.81(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00 119.00   0.50    0.15    --   45.63  52.00 176.00  172
  2  ω    116.00 176.00   0.50    0.62    --  103.81  61.00  90.00  120
  3  ω    109.00 134.00   0.50    0.62    --  103.81  52.00 176.00   50
  4  ω     33.00  62.00   0.50    0.62    --  103.81 -52.00  31.00   58
  5  ω     37.00  75.00   0.50    0.62    --  103.81 -61.00  60.00   76
  6  ω     37.00 104.00   0.50    0.62    --  103.81 -77.00 -30.00  134
  7  ω     44.00  73.00   0.50    0.62    --  103.81 -61.00-120.00   58
  8  ω    -26.00  53.00   0.50    0.15    --   45.63 -52.00  31.00  158
  9  ω    -89.00 -63.00   0.50    0.15    --  -45.63 -52.00  31.00   52
 10  ω   -171.00 -90.00   0.50    0.62    -- -103.81 -52.00  31.00  162
 11  ω   -172.00 -87.00   0.50    0.62    -- -103.81 -61.00 120.00  170
 12  ω   -107.00 -37.00   0.50    0.62    -- -103.81 125.00-150.00  140
 13  ω    -69.00 -32.00   0.50    0.62    -- -103.81  77.00 -60.00   74
 14  ω    -66.00 -35.00   0.50    0.62    -- -103.81  61.00-180.00   62
 15  ω    -98.00 -31.00   0.50    0.62    -- -103.81  77.00-150.00  134
 16  ω    -21.00  29.00   0.50    0.15    --  -45.63  19.00 -30.00  100
 17  ω    -29.00  27.00   0.50    0.15    --  -45.63  52.00 176.00  112
 18  ω    -67.00 -39.00   0.50    0.62    -- -103.81  61.00  90.00   56
 19  ω    -57.00 -32.00   0.50    0.62    -- -103.81  61.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1234863000
_diffrn_orient_matrix_UB_12      0.0426712000
_diffrn_orient_matrix_UB_13      -0.0558339000
_diffrn_orient_matrix_UB_21      -0.0539657000
_diffrn_orient_matrix_UB_22      -0.1377278000
_diffrn_orient_matrix_UB_23      0.0641922000
_diffrn_orient_matrix_UB_31      -0.0118156000
_diffrn_orient_matrix_UB_32      0.1804369000
_diffrn_orient_matrix_UB_33      0.0621979000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1975
_reflns_number_total             2182
_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       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.142a 64-bit (release 17-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      1.078
_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)+(0.1143P)²+0.1294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1732
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C12(H12), C13(H13), C2(H2), C9(H9), C5(H5)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C3(H3A,H3B,H3C)
;
_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
N1 N 0.01333(10) 0.59873(18) 0.61229(7) 0.0456(3) Uani 1 1 d . . . . .
O1 O 0.58043(10) 1.0333(2) 0.61680(9) 0.0725(4) Uani 1 1 d . . . . .
C1 C 0.12186(12) 0.5153(2) 0.64446(9) 0.0439(4) Uani 1 1 d . . . . .
C4 C 0.10360(13) 0.3389(2) 0.68768(9) 0.0500(4) Uani 1 1 d . . . . .
H4 H 0.161534 0.250897 0.715813 0.060 Uiso 1 1 calc R U . . .
O2 O 0.65729(12) 0.7277(3) 0.60905(15) 0.1038(6) Uani 1 1 d . . . . .
C6 C 0.23505(12) 0.6055(2) 0.63542(9) 0.0459(4) Uani 1 1 d . . . . .
C8 C -0.01779(14) 0.3152(2) 0.68182(10) 0.0529(4) Uani 1 1 d . . . . .
H8 H -0.054894 0.209582 0.705626 0.064 Uiso 1 1 calc R U . . .
C10 C -0.01264(15) 0.7831(2) 0.56050(11) 0.0583(4) Uani 1 1 d . . . . .
H10A H -0.004687 0.895006 0.601780 0.087 Uiso 1 1 calc R U . . .
H10B H -0.091531 0.778093 0.526276 0.087 Uiso 1 1 calc R U . . .
H10C H 0.041140 0.798102 0.519223 0.087 Uiso 1 1 calc R U . . .
C12 C -0.07120(13) 0.4757(2) 0.63481(10) 0.0517(4) Uani 1 1 d . . . . .
H12 H -0.151748 0.497924 0.620407 0.062 Uiso 1 1 calc R U . . .
C13 C 0.26236(14) 0.8061(2) 0.65426(11) 0.0558(4) Uani 1 1 d . . . . .
H13 H 0.205904 0.890814 0.670386 0.067 Uiso 1 1 calc R U . . .
C7 C 0.45785(13) 0.7574(3) 0.62581(10) 0.0548(4) Uani 1 1 d . . . . .
C2 C 0.37189(14) 0.8817(2) 0.64940(11) 0.0578(4) Uani 1 1 d . . . . .
H2 H 0.388299 1.016353 0.661971 0.069 Uiso 1 1 calc R U . . .
C9 C 0.32202(14) 0.4823(3) 0.61208(12) 0.0595(4) Uani 1 1 d . . . . .
H9 H 0.305564 0.347896 0.598709 0.071 Uiso 1 1 calc R U . . .
C5 C 0.43170(14) 0.5564(3) 0.60852(13) 0.0651(5) Uani 1 1 d . . . . .
H5 H 0.489019 0.470859 0.594352 0.078 Uiso 1 1 calc R U . . .
C11 C 0.57579(14) 0.8335(3) 0.61662(12) 0.0645(5) Uani 1 1 d . . . . .
C3 C 0.69165(16) 1.1206(4) 0.60910(14) 0.0825(7) Uani 1 1 d . . . . .
H3A H 0.709522 1.088504 0.550369 0.124 Uiso 1 1 calc R U . . .
H3B H 0.751960 1.068010 0.656382 0.124 Uiso 1 1 calc R U . . .
H3C H 0.687630 1.263550 0.615398 0.124 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
N1 C1 1.3768(18) . ?
N1 C10 1.4524(19) . ?
N1 C12 1.3679(19) . ?
O1 C11 1.333(2) . ?
O1 C3 1.440(2) . ?
C1 C4 1.376(2) . ?
C1 C6 1.4732(19) . ?
C4 H4 0.9300 . ?
C4 C8 1.403(2) . ?
O2 C11 1.202(2) . ?
C6 C13 1.392(2) . ?
C6 C9 1.395(2) . ?
C8 H8 0.9300 . ?
C8 C12 1.362(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C2 1.381(2) . ?
C7 C2 1.392(2) . ?
C7 C5 1.387(3) . ?
C7 C11 1.490(2) . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
C9 C5 1.375(2) . ?
C5 H5 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?

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
C1 N1 C10 127.67(12) . . ?
C12 N1 C1 108.83(12) . . ?
C12 N1 C10 123.49(13) . . ?
C11 O1 C3 116.14(16) . . ?
N1 C1 C6 125.10(13) . . ?
C4 C1 N1 107.26(12) . . ?
C4 C1 C6 127.61(13) . . ?
C1 C4 H4 126.0 . . ?
C1 C4 C8 107.97(13) . . ?
C8 C4 H4 126.0 . . ?
C13 C6 C1 123.17(13) . . ?
C13 C6 C9 117.97(14) . . ?
C9 C6 C1 118.76(13) . . ?
C4 C8 H8 126.4 . . ?
C12 C8 C4 107.28(13) . . ?
C12 C8 H8 126.4 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C12 H12 125.7 . . ?
C8 C12 N1 108.66(13) . . ?
C8 C12 H12 125.7 . . ?
C6 C13 H13 119.4 . . ?
C2 C13 C6 121.12(14) . . ?
C2 C13 H13 119.4 . . ?
C2 C7 C11 122.28(16) . . ?
C5 C7 C2 118.71(14) . . ?
C5 C7 C11 118.99(15) . . ?
C13 C2 C7 120.39(15) . . ?
C13 C2 H2 119.8 . . ?
C7 C2 H2 119.8 . . ?
C6 C9 H9 119.5 . . ?
C5 C9 C6 121.03(15) . . ?
C5 C9 H9 119.5 . . ?
C7 C5 H5 119.6 . . ?
C9 C5 C7 120.76(15) . . ?
C9 C5 H5 119.6 . . ?
O1 C11 C7 112.21(15) . . ?
O2 C11 O1 123.71(17) . . ?
O2 C11 C7 124.1(2) . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

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
N1 C1 C4 C8 -0.14(16) . . . . ?
N1 C1 C6 C13 46.1(2) . . . . ?
N1 C1 C6 C9 -137.81(15) . . . . ?
C1 N1 C12 C8 0.56(16) . . . . ?
C1 C4 C8 C12 0.47(16) . . . . ?
C1 C6 C13 C2 176.59(14) . . . . ?
C1 C6 C9 C5 -175.79(15) . . . . ?
C4 C1 C6 C13 -131.95(17) . . . . ?
C4 C1 C6 C9 44.2(2) . . . . ?
C4 C8 C12 N1 -0.63(16) . . . . ?
C6 C1 C4 C8 178.17(13) . . . . ?
C6 C13 C2 C7 -0.3(3) . . . . ?
C6 C9 C5 C7 -1.7(3) . . . . ?
C10 N1 C1 C4 -178.65(13) . . . . ?
C10 N1 C1 C6 3.0(2) . . . . ?
C10 N1 C12 C8 179.03(13) . . . . ?
C12 N1 C1 C4 -0.25(16) . . . . ?
C12 N1 C1 C6 -178.62(12) . . . . ?
C13 C6 C9 C5 0.5(2) . . . . ?
C2 C7 C5 C9 1.8(3) . . . . ?
C2 C7 C11 O1 -11.5(2) . . . . ?
C2 C7 C11 O2 169.2(2) . . . . ?
C9 C6 C13 C2 0.4(2) . . . . ?
C5 C7 C2 C13 -0.8(2) . . . . ?
C5 C7 C11 O1 167.21(15) . . . . ?
C5 C7 C11 O2 -12.2(3) . . . . ?
C11 C7 C2 C13 177.87(15) . . . . ?
C11 C7 C5 C9 -176.94(15) . . . . ?
C3 O1 C11 O2 -1.2(3) . . . . ?
C3 O1 C11 C7 179.41(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.606
_oxdiff_exptl_absorpt_empirical_full_min 0.169
