# Supplementary Information (SI) for Green 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_lk-2-ea_auto
_database_code_depnum_ccdc_archive 'CCDC 2425206'
loop_
_audit_author_name
_audit_author_address
'Kai Li'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2025-02-19 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_audit_creation_date             2024-05-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H12 N2 O'
_chemical_formula_sum            'C14 H12 N2 O'
_chemical_formula_weight         224.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20h20n2o2
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                   9.0084(3)
_cell_length_b                   8.7513(2)
_cell_length_c                   15.7194(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.743(3)
_cell_angle_gamma                90
_cell_volume                     1221.37(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2231
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8420
_cell_measurement_theta_min      5.7100
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4213
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.887
_diffrn_reflns_theta_min         4.981
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -124.00  41.00   1.00    2.00    --  -40.01   0.00-120.00  165
  2  ω     71.00  98.00   1.00    2.00    --   40.01 178.00-150.00   27
  3  ω    -19.00  16.00   1.00    2.00    --   40.01 -77.00  30.00   35
  4  ω    150.00 177.00   1.00    4.00    --  105.74  77.00   0.00   27
  5  ω     90.00 177.00   1.00    4.00    --  105.74  45.00  30.00   87
  6  ω     73.00 111.00   1.00    4.00    --  105.74-125.00-120.00   38
  7  ω    120.00 147.00   1.00    4.00    --  105.74  77.00 -90.00   27
  8  ω    130.00 167.00   1.00    4.00    --  105.74 125.00 -60.00   37
  9  ω     33.00 130.00   1.00    4.00    --  105.74 -61.00-120.00   97
 10  ω    108.00 175.00   1.00    4.00    --  105.74  77.00 -30.00   67
 11  ω    112.00 157.00   1.00    4.00    --  105.74  77.00 -60.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0181536000
_diffrn_orient_matrix_UB_12      -0.0881697000
_diffrn_orient_matrix_UB_13      0.0859047000
_diffrn_orient_matrix_UB_21      0.1658784000
_diffrn_orient_matrix_UB_22      0.0507172000
_diffrn_orient_matrix_UB_23      0.0212681000
_diffrn_orient_matrix_UB_31      -0.0474548000
_diffrn_orient_matrix_UB_32      0.1437023000
_diffrn_orient_matrix_UB_33      0.0453871000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1887
_reflns_number_total             2345
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.061
_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)+(0.0474P)²+0.1449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1025
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C8(H8), C7(H7)
1.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C5(H5), C13(H13), C12(H12), C2(H2), C6(H6), C11(H11), C1(H1A)
1.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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 0.58284(11) 0.88801(10) 0.29176(7) 0.0540(3) Uani 1 1 d . . . . .
H1 H 0.4974 0.9169 0.2950 0.081 Uiso 1 1 calc R U . . .
N1 N 0.69316(13) 0.53327(13) 0.20797(7) 0.0484(3) Uani 1 1 d . . . . .
C8 C 0.58531(14) 0.72768(14) 0.28744(8) 0.0396(3) Uani 1 1 d . . . . .
H8 H 0.4872 0.6918 0.2575 0.048 Uiso 1 1 calc R U . . .
C9 C 0.70537(14) 0.67714(15) 0.23722(8) 0.0400(3) Uani 1 1 d . . . . .
C4 C 0.49031(15) 0.68120(15) 0.43017(8) 0.0423(3) Uani 1 1 d . . . . .
C7 C 0.61682(14) 0.65572(16) 0.37944(8) 0.0433(3) Uani 1 1 d . . . . .
H7 H 0.6272 0.5452 0.3724 0.052 Uiso 1 1 calc R U . . .
C3 C 0.36030(16) 0.59466(17) 0.40909(9) 0.0523(4) Uani 1 1 d . . . . .
H3 H 0.3538 0.5219 0.3655 0.063 Uiso 1 1 calc R U . . .
C10 C 0.82360(16) 0.77100(17) 0.22540(10) 0.0520(4) Uani 1 1 d . . . . .
H10 H 0.8298 0.8704 0.2467 0.062 Uiso 1 1 calc R U . . .
C5 C 0.49885(17) 0.78709(17) 0.49598(10) 0.0531(4) Uani 1 1 d . . . . .
H5 H 0.5855 0.8456 0.5111 0.064 Uiso 1 1 calc R U . . .
C13 C 0.80033(18) 0.48182(19) 0.16537(10) 0.0591(4) Uani 1 1 d . . . . .
H13 H 0.7927 0.3821 0.1447 0.071 Uiso 1 1 calc R U . . .
C14 C 0.76185(17) 0.7132(2) 0.42417(10) 0.0621(4) Uani 1 1 d . . . . .
C12 C 0.92051(18) 0.5684(2) 0.15073(10) 0.0640(4) Uani 1 1 d . . . . .
H12 H 0.9922 0.5286 0.1207 0.077 Uiso 1 1 calc R U . . .
C2 C 0.24063(18) 0.6154(2) 0.45212(11) 0.0620(4) Uani 1 1 d . . . . .
H2 H 0.1536 0.5574 0.4371 0.074 Uiso 1 1 calc R U . . .
C6 C 0.37826(19) 0.8064(2) 0.53955(10) 0.0635(4) Uani 1 1 d . . . . .
H6 H 0.3848 0.8773 0.5841 0.076 Uiso 1 1 calc R U . . .
C11 C 0.93205(18) 0.7149(2) 0.18156(11) 0.0641(4) Uani 1 1 d . . . . .
H11 H 1.0126 0.7762 0.1730 0.077 Uiso 1 1 calc R U . . .
C1 C 0.24987(19) 0.7216(2) 0.51722(10) 0.0643(5) Uani 1 1 d . . . . .
H1A H 0.1689 0.7359 0.5461 0.077 Uiso 1 1 calc R U . . .
N2 N 0.87478(18) 0.7595(3) 0.45658(11) 0.1004(7) Uani 1 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 H1 0.8200 . ?
O1 C8 1.4051(15) . ?
N1 C9 1.3385(17) . ?
N1 C13 1.3423(18) . ?
C8 H8 0.9800 . ?
C8 C9 1.5091(17) . ?
C8 C7 1.5587(17) . ?
C9 C10 1.3823(19) . ?
C4 C7 1.5140(18) . ?
C4 C3 1.3869(19) . ?
C4 C5 1.381(2) . ?
C7 H7 0.9800 . ?
C7 C14 1.464(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.378(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.372(2) . ?
C14 N2 1.133(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.368(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.375(2) . ?
C6 H6 0.9300 . ?
C6 C1 1.369(2) . ?
C11 H11 0.9300 . ?
C1 H1A 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
C8 O1 H1 109.5 . . ?
C9 N1 C13 117.56(12) . . ?
O1 C8 H8 108.9 . . ?
O1 C8 C9 109.67(10) . . ?
O1 C8 C7 111.13(11) . . ?
C9 C8 H8 108.9 . . ?
C9 C8 C7 109.44(10) . . ?
C7 C8 H8 108.9 . . ?
N1 C9 C8 115.53(11) . . ?
N1 C9 C10 122.22(12) . . ?
C10 C9 C8 122.20(12) . . ?
C3 C4 C7 118.31(12) . . ?
C5 C4 C7 122.81(12) . . ?
C5 C4 C3 118.88(13) . . ?
C8 C7 H7 107.4 . . ?
C4 C7 C8 113.20(10) . . ?
C4 C7 H7 107.4 . . ?
C14 C7 C8 108.32(11) . . ?
C14 C7 C4 112.73(11) . . ?
C14 C7 H7 107.4 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.67(14) . . ?
C2 C3 H3 119.7 . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.89(14) . . ?
C11 C10 H10 120.6 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.12(14) . . ?
C6 C5 H5 119.9 . . ?
N1 C13 H13 118.2 . . ?
N1 C13 C12 123.56(15) . . ?
C12 C13 H13 118.2 . . ?
N2 C14 C7 178.00(18) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 C13 118.20(14) . . ?
C11 C12 H12 120.9 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.03(15) . . ?
C1 C2 H2 120.0 . . ?
C5 C6 H6 119.8 . . ?
C1 C6 C5 120.33(15) . . ?
C1 C6 H6 119.8 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.56(15) . . ?
C12 C11 H11 120.2 . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 C2 119.97(15) . . ?
C6 C1 H1A 120.0 . . ?

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 C8 C9 N1 -162.36(11) . . . . ?
O1 C8 C9 C10 20.29(17) . . . . ?
O1 C8 C7 C4 67.07(14) . . . . ?
O1 C8 C7 C14 -58.73(14) . . . . ?
N1 C9 C10 C11 0.4(2) . . . . ?
N1 C13 C12 C11 0.3(3) . . . . ?
C8 C9 C10 C11 177.58(13) . . . . ?
C9 N1 C13 C12 0.2(2) . . . . ?
C9 C8 C7 C4 -171.67(11) . . . . ?
C9 C8 C7 C14 62.54(14) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C4 C3 C2 C1 -0.6(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C7 C8 C9 N1 75.49(14) . . . . ?
C7 C8 C9 C10 -101.86(14) . . . . ?
C7 C4 C3 C2 -178.75(13) . . . . ?
C7 C4 C5 C6 179.29(13) . . . . ?
C3 C4 C7 C8 75.56(15) . . . . ?
C3 C4 C7 C14 -161.04(14) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C3 C2 C1 C6 -0.3(2) . . . . ?
C5 C4 C7 C8 -104.14(15) . . . . ?
C5 C4 C7 C14 19.26(19) . . . . ?
C5 C4 C3 C2 1.0(2) . . . . ?
C5 C6 C1 C2 0.8(3) . . . . ?
C13 N1 C9 C8 -177.87(12) . . . . ?
C13 N1 C9 C10 -0.5(2) . . . . ?
C13 C12 C11 C10 -0.4(3) . . . . ?

_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.776
