# Supplementary Information (SI) for ChemComm.
# 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_zxj_syl1
_database_code_depnum_ccdc_archive 'CCDC 2403384'
loop_
_audit_author_name
_audit_author_address
'ZHAO xiaojing'
;Yunnan Minzu University
China
;
_audit_update_record             
;
2024-11-18 deposited with the CCDC.	2025-09-25 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H11 N O2'
_chemical_formula_sum            'C11 H11 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         189.21

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.1083(4)
_cell_length_b                   6.8867(2)
_cell_length_c                   21.4225(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.066(2)
_cell_angle_gamma                90
_cell_volume                     1932.61(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5766
_cell_measurement_theta_min      3.8920
_cell_measurement_theta_max      68.1743
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.170
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800

_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            15426
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_theta_min         3.89
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_full        68.21
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
;

_reflns_number_total             3519
_reflns_number_gt                2690
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1324
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_number_reflns         3519
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.6021P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.19416(11) 0.4651(3) 0.27079(7) 0.0555(5) Uani d . . . 1 . .
O O2 0.62066(11) 0.3191(3) 0.39374(6) 0.0522(4) Uani d . . . 1 . .
O O3 0.77415(10) 0.2415(2) 0.57463(7) 0.0456(4) Uani d . . . 1 . .
O O4 0.34572(10) 0.3146(2) 0.44913(6) 0.0441(4) Uani d . . . 1 . .
N N1 0.36726(11) 0.4296(2) 0.27550(7) 0.0322(4) Uani d . . . 1 . .
N N2 0.60185(11) 0.1997(2) 0.56363(7) 0.0311(4) Uani d . . . 1 . .
C C1 0.37665(16) 0.4514(4) 0.20820(9) 0.0467(6) Uani d . . . 1 . .
H H4 0.309279 0.477534 0.188694 0.07 Uiso calc U . R 1 . .
H H5 0.404316 0.331521 0.190872 0.07 Uiso calc U . R 1 . .
H H1 0.422674 0.559717 0.19983 0.07 Uiso calc U . R 1 . .
C C2 0.45224(13) 0.3949(3) 0.31348(8) 0.0287(4) Uani d . . . 1 . .
H H6 0.442321 0.37678 0.356801 0.034 Uiso calc U . R 1 . .
C C3 0.54811(13) 0.3849(3) 0.29372(8) 0.0293(4) Uani d . . . 1 . .
H H11 0.560618 0.398547 0.250538 0.035 Uiso calc U . R 1 . .
C C4 0.63332(14) 0.3529(3) 0.33844(8) 0.0312(4) Uani d . . . 1 . .
C C5 0.73917(13) 0.3705(3) 0.31527(8) 0.0269(4) Uani d . . . 1 . .
C C6 0.76158(13) 0.3358(3) 0.25324(8) 0.0288(4) Uani d . . . 1 . .
H H10 0.708603 0.299612 0.224112 0.035 Uiso calc U . R 1 . .
C C7 0.86071(14) 0.3537(3) 0.23379(8) 0.0333(4) Uani d . . . 1 . .
H H9 0.875498 0.326624 0.191585 0.04 Uiso calc U . R 1 . .
C C8 0.93837(14) 0.4106(3) 0.27512(9) 0.0344(4) Uani d . . . 1 . .
H H2 1.005919 0.425975 0.26124 0.041 Uiso calc U . R 1 . .
C C9 0.27277(15) 0.4380(3) 0.30073(10) 0.0413(5) Uani d . . . 1 . .
H H3 0.268798 0.421335 0.344602 0.05 Uiso calc U . R 1 . .
C C10 0.91685(14) 0.4452(3) 0.33709(9) 0.0346(4) Uani d . . . 1 . .
H H7 0.969943 0.483447 0.365857 0.042 Uiso calc U . R 1 . .
C C11 0.81822(14) 0.4242(3) 0.35711(8) 0.0332(4) Uani d . . . 1 . .
H H8 0.804223 0.446585 0.399713 0.04 Uiso calc U . R 1 . .
C C12 0.02908(15) 0.1467(3) 0.56024(10) 0.0380(5) Uani d . . . 1 . .
H H12 -0.03868 0.129433 0.573542 0.046 Uiso calc U . R 1 . .
C C13 0.10924(15) 0.0547(3) 0.59141(9) 0.0376(5) Uani d . . . 1 . .
H H16 0.09657 -0.026537 0.626115 0.045 Uiso calc U . R 1 . .
C C14 0.20823(14) 0.0803(3) 0.57231(9) 0.0334(4) Uani d . . . 1 . .
H H15 0.262874 0.014975 0.593727 0.04 Uiso calc U . R 1 . .
C C15 0.22846(14) 0.2011(3) 0.52195(8) 0.0304(4) Uani d . . . 1 . .
C C16 0.33396(14) 0.2399(3) 0.50042(8) 0.0321(4) Uani d . . . 1 . .
C C17 0.41987(14) 0.1934(3) 0.54273(8) 0.0321(4) Uani d . . . 1 . .
H H14 0.408311 0.132889 0.581691 0.038 Uiso calc U . R 1 . .
C C18 0.51541(14) 0.2360(3) 0.52678(8) 0.0316(4) Uani d . . . 1 . .
H H19 0.524155 0.295367 0.487303 0.038 Uiso calc U . R 1 . .
C C19 0.59350(16) 0.1083(4) 0.62449(9) 0.0436(5) Uani d . . . 1 . .
H H21 0.661954 0.084302 0.642763 0.065 Uiso calc U . R 1 . .
H H20 0.556915 -0.015204 0.619667 0.065 Uiso calc U . R 1 . .
H H13 0.556002 0.194217 0.652019 0.065 Uiso calc U . R 1 . .
C C20 0.69571(14) 0.2571(3) 0.54353(9) 0.0345(4) Uani d . . . 1 . .
H H22 0.699092 0.311985 0.502972 0.041 Uiso calc U . R 1 . .
C C21 0.04771(15) 0.2644(3) 0.50943(10) 0.0383(5) Uani d . . . 1 . .
H H17 -0.007642 0.326192 0.487564 0.046 Uiso calc U . R 1 . .
C C22 0.14631(14) 0.2925(3) 0.49030(9) 0.0347(4) Uani d . . . 1 . .
H H18 0.158358 0.374078 0.455568 0.042 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 . 1.209(2) ?
O2 C4 . 1.224(2) ?
O3 C20 . 1.210(2) ?
O4 C16 . 1.228(2) ?
N1 C9 . 1.370(2) ?
N1 C2 . 1.376(2) ?
N1 C1 . 1.459(2) ?
N2 C20 . 1.376(2) ?
N2 C18 . 1.380(2) ?
N2 C19 . 1.456(2) ?
C1 H4 . 0.98 ?
C1 H5 . 0.98 ?
C1 H1 . 0.98 ?
C2 C3 . 1.342(2) ?
C2 H6 . 0.95 ?
C3 C4 . 1.462(2) ?
C3 H11 . 0.95 ?
C4 C5 . 1.495(2) ?
C5 C6 . 1.392(2) ?
C5 C11 . 1.395(2) ?
C6 C7 . 1.384(2) ?
C6 H10 . 0.95 ?
C7 C8 . 1.382(3) ?
C7 H9 . 0.95 ?
C8 C10 . 1.388(3) ?
C8 H2 . 0.95 ?
C9 H3 . 0.95 ?
C10 C11 . 1.384(3) ?
C10 H7 . 0.95 ?
C11 H8 . 0.95 ?
C12 C13 . 1.379(3) ?
C12 C21 . 1.386(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.386(3) ?
C13 H16 . 0.95 ?
C14 C15 . 1.395(3) ?
C14 H15 . 0.95 ?
C15 C22 . 1.401(3) ?
C15 C16 . 1.497(3) ?
C16 C17 . 1.456(2) ?
C17 C18 . 1.342(3) ?
C17 H14 . 0.95 ?
C18 H19 . 0.95 ?
C19 H21 . 0.98 ?
C19 H20 . 0.98 ?
C19 H13 . 0.98 ?
C20 H22 . 0.95 ?
C21 C22 . 1.384(3) ?
C21 H17 . 0.95 ?
C22 H18 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N1 C2 . . 119.86(16) ?
C9 N1 C1 . . 119.68(15) ?
C2 N1 C1 . . 120.44(16) ?
C20 N2 C18 . . 119.59(16) ?
C20 N2 C19 . . 120.10(15) ?
C18 N2 C19 . . 120.26(16) ?
N1 C1 H4 . . 109.5 ?
N1 C1 H5 . . 109.5 ?
H4 C1 H5 . . 109.5 ?
N1 C1 H1 . . 109.5 ?
H4 C1 H1 . . 109.5 ?
H5 C1 H1 . . 109.5 ?
C3 C2 N1 . . 124.71(17) ?
C3 C2 H6 . . 117.6 ?
N1 C2 H6 . . 117.6 ?
C2 C3 C4 . . 120.21(16) ?
C2 C3 H11 . . 119.9 ?
C4 C3 H11 . . 119.9 ?
O2 C4 C3 . . 122.39(17) ?
O2 C4 C5 . . 119.75(16) ?
C3 C4 C5 . . 117.82(15) ?
C6 C5 C11 . . 118.77(17) ?
C6 C5 C4 . . 122.23(15) ?
C11 C5 C4 . . 119.00(16) ?
C7 C6 C5 . . 120.31(16) ?
C7 C6 H10 . . 119.8 ?
C5 C6 H10 . . 119.8 ?
C8 C7 C6 . . 120.69(17) ?
C8 C7 H9 . . 119.7 ?
C6 C7 H9 . . 119.7 ?
C7 C8 C10 . . 119.42(17) ?
C7 C8 H2 . . 120.3 ?
C10 C8 H2 . . 120.3 ?
O1 C9 N1 . . 124.24(19) ?
O1 C9 H3 . . 117.9 ?
N1 C9 H3 . . 117.9 ?
C11 C10 C8 . . 120.18(17) ?
C11 C10 H7 . . 119.9 ?
C8 C10 H7 . . 119.9 ?
C10 C11 C5 . . 120.60(17) ?
C10 C11 H8 . . 119.7 ?
C5 C11 H8 . . 119.7 ?
C13 C12 C21 . . 119.75(19) ?
C13 C12 H12 . . 120.1 ?
C21 C12 H12 . . 120.1 ?
C12 C13 C14 . . 120.27(19) ?
C12 C13 H16 . . 119.9 ?
C14 C13 H16 . . 119.9 ?
C13 C14 C15 . . 120.68(17) ?
C13 C14 H15 . . 119.7 ?
C15 C14 H15 . . 119.7 ?
C14 C15 C22 . . 118.54(17) ?
C14 C15 C16 . . 123.22(16) ?
C22 C15 C16 . . 118.23(17) ?
O4 C16 C17 . . 122.00(17) ?
O4 C16 C15 . . 119.84(16) ?
C17 C16 C15 . . 118.12(16) ?
C18 C17 C16 . . 120.10(17) ?
C18 C17 H14 . . 120.0 ?
C16 C17 H14 . . 120.0 ?
C17 C18 N2 . . 124.69(17) ?
C17 C18 H19 . . 117.7 ?
N2 C18 H19 . . 117.7 ?
N2 C19 H21 . . 109.5 ?
N2 C19 H20 . . 109.5 ?
H21 C19 H20 . . 109.5 ?
N2 C19 H13 . . 109.5 ?
H21 C19 H13 . . 109.5 ?
H20 C19 H13 . . 109.5 ?
O3 C20 N2 . . 123.64(18) ?
O3 C20 H22 . . 118.2 ?
N2 C20 H22 . . 118.2 ?
C22 C21 C12 . . 120.49(18) ?
C22 C21 H17 . . 119.8 ?
C12 C21 H17 . . 119.8 ?
C21 C22 C15 . . 120.24(19) ?
C21 C22 H18 . . 119.9 ?
C15 C22 H18 . . 119.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C2 C3 . . . . -179.64(19) ?
C1 N1 C2 C3 . . . . 2.4(3) ?
N1 C2 C3 C4 . . . . 178.17(17) ?
C2 C3 C4 O2 . . . . 5.9(3) ?
C2 C3 C4 C5 . . . . -171.67(17) ?
O2 C4 C5 C6 . . . . 155.2(2) ?
C3 C4 C5 C6 . . . . -27.1(3) ?
O2 C4 C5 C11 . . . . -25.0(3) ?
C3 C4 C5 C11 . . . . 152.65(18) ?
C11 C5 C6 C7 . . . . 0.3(3) ?
C4 C5 C6 C7 . . . . 180.00(18) ?
C5 C6 C7 C8 . . . . -1.5(3) ?
C6 C7 C8 C10 . . . . 1.6(3) ?
C2 N1 C9 O1 . . . . -179.0(2) ?
C1 N1 C9 O1 . . . . -1.0(3) ?
C7 C8 C10 C11 . . . . -0.5(3) ?
C8 C10 C11 C5 . . . . -0.8(3) ?
C6 C5 C11 C10 . . . . 0.9(3) ?
C4 C5 C11 C10 . . . . -178.86(18) ?
C21 C12 C13 C14 . . . . 0.3(3) ?
C12 C13 C14 C15 . . . . 0.8(3) ?
C13 C14 C15 C22 . . . . -1.4(3) ?
C13 C14 C15 C16 . . . . 177.92(17) ?
C14 C15 C16 O4 . . . . 165.49(19) ?
C22 C15 C16 O4 . . . . -15.2(3) ?
C14 C15 C16 C17 . . . . -16.8(3) ?
C22 C15 C16 C17 . . . . 162.51(17) ?
O4 C16 C17 C18 . . . . 1.5(3) ?
C15 C16 C17 C18 . . . . -176.20(17) ?
C16 C17 C18 N2 . . . . 179.41(18) ?
C20 N2 C18 C17 . . . . -177.30(19) ?
C19 N2 C18 C17 . . . . 0.3(3) ?
C18 N2 C20 O3 . . . . 175.30(19) ?
C19 N2 C20 O3 . . . . -2.3(3) ?
C13 C12 C21 C22 . . . . -0.9(3) ?
C12 C21 C22 C15 . . . . 0.4(3) ?
C14 C15 C22 C21 . . . . 0.8(3) ?
C16 C15 C22 C21 . . . . -178.57(17) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H6 O4 . 0.95 2.42 3.316(2) 156.1 ?
C9 H3 O4 . 0.95 2.53 3.395(2) 151.1 ?
C18 H19 O2 . 0.95 2.41 3.262(2) 148.4 ?
C20 H22 O2 . 0.95 2.52 3.350(2) 145.6 ?

