# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_lxg1a
_database_code_depnum_ccdc_archive 'CCDC 2251050'
loop_
_audit_author_name
_audit_author_address
'Jun He'
;South Central Minzu University
China
;
_audit_update_record             
;
2023-03-23 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         177.20

_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                   6.7030(4)
_cell_length_b                   9.0452(6)
_cell_length_c                   15.0090(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.234(2)
_cell_angle_gamma                90
_cell_volume                     908.55(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      4.8892
_cell_measurement_theta_max      74.5551
_cell_measurement_temperature    273.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376

_exptl_absorpt_coefficient_mu    0.743
_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  0.73
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
;

_diffrn_ambient_temperature      273.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            14437
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_theta_min         5.91
_diffrn_reflns_theta_max         74.55
_diffrn_reflns_theta_full        74.55
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             1838
_reflns_number_gt                1775
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1107
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_number_reflns         1838
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²+0.1205P] 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         0.214
_refine_diff_density_min         -0.164
_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       ?
_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_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 0.08524(13) 0.35948(12) 0.58274(6) 0.0668(3) Uani d . . . 1 . .
C C1 0.24198(17) 0.30779(14) 0.55846(8) 0.0515(3) Uani d . . . 1 . .
H H1 0.308002 0.23921 0.595684 0.062 Uiso calc U . R 1 . .
O O2 0.76869(15) 0.36718(12) 0.24897(7) 0.0682(3) Uani d . . . 1 . .
C C2 0.33068(15) 0.34497(12) 0.47738(7) 0.0441(3) Uani d . . . 1 . .
N N1 0.24680(13) 0.44835(10) 0.41748(6) 0.0445(2) Uani d . . . 1 . .
H H1N 0.137802 0.49564 0.425175 0.053 Uiso calc U . R 1 . .
C C10 0.2605(2) 0.48684(15) 0.18359(9) 0.0619(3) Uani d . . . 1 . .
H H10A 0.37498 0.428482 0.170718 0.093 Uiso calc U . R 1 . .
H H10B 0.234145 0.557336 0.136575 0.093 Uiso calc U . R 1 . .
H H10C 0.1466 0.423459 0.188001 0.093 Uiso calc U . R 1 . .
C C9 0.30121(19) 0.56786(13) 0.27128(8) 0.0541(3) Uani d . . . 1 . .
H H9A 0.408565 0.638276 0.264799 0.065 Uiso calc U . R 1 . .
H H9B 0.182785 0.622727 0.285478 0.065 Uiso calc U . R 1 . .
C C8 0.35733(16) 0.46499(12) 0.34621(7) 0.0442(3) Uani d . . . 1 . .
C C7 0.51998(15) 0.36817(12) 0.35943(7) 0.0440(3) Uani d . . . 1 . .
C C3 0.50304(15) 0.29460(12) 0.44040(7) 0.0432(3) Uani d . . . 1 . .
C C4 0.67194(17) 0.18880(15) 0.46064(8) 0.0536(3) Uani d . . . 1 . .
H H4A 0.623154 0.088822 0.467972 0.064 Uiso calc U . R 1 . .
H H4B 0.750256 0.217763 0.514117 0.064 Uiso calc U . R 1 . .
C C6 0.70067(17) 0.32207(13) 0.31733(8) 0.0498(3) Uani d . . . 1 . .
C C5 0.79508(18) 0.20182(15) 0.37708(9) 0.0577(3) Uani d . . . 1 . .
H H5A 0.932408 0.227329 0.394358 0.069 Uiso calc U . R 1 . .
H H5B 0.794458 0.108319 0.345418 0.069 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 C1 . 1.2241(14) ?
C1 C2 . 1.4244(15) ?
C1 H1 . 0.93 ?
O2 C6 . 1.2165(14) ?
C2 C3 . 1.3867(14) ?
C2 N1 . 1.3935(14) ?
N1 C8 . 1.3436(13) ?
N1 H1N . 0.86 ?
C10 C9 . 1.5176(18) ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
C9 C8 . 1.4914(16) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C8 C7 . 1.4038(15) ?
C7 C3 . 1.3958(15) ?
C7 C6 . 1.4582(14) ?
C3 C4 . 1.5003(16) ?
C4 C5 . 1.5443(17) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C6 C5 . 1.5244(18) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?

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
O1 C1 C2 . . 124.81(12) ?
O1 C1 H1 . . 117.6 ?
C2 C1 H1 . . 117.6 ?
C3 C2 N1 . . 106.09(9) ?
C3 C2 C1 . . 131.44(11) ?
N1 C2 C1 . . 122.48(10) ?
C8 N1 C2 . . 111.61(9) ?
C8 N1 H1N . . 124.2 ?
C2 N1 H1N . . 124.2 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C8 C9 C10 . . 112.21(10) ?
C8 C9 H9A . . 109.2 ?
C10 C9 H9A . . 109.2 ?
C8 C9 H9B . . 109.2 ?
C10 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
N1 C8 C7 . . 106.04(9) ?
N1 C8 C9 . . 122.90(10) ?
C7 C8 C9 . . 131.05(10) ?
C3 C7 C8 . . 108.65(9) ?
C3 C7 C6 . . 110.57(10) ?
C8 C7 C6 . . 140.77(11) ?
C2 C3 C7 . . 107.61(10) ?
C2 C3 C4 . . 139.88(10) ?
C7 C3 C4 . . 112.51(9) ?
C3 C4 C5 . . 102.63(9) ?
C3 C4 H4A . . 111.2 ?
C5 C4 H4A . . 111.2 ?
C3 C4 H4B . . 111.2 ?
C5 C4 H4B . . 111.2 ?
H4A C4 H4B . . 109.2 ?
O2 C6 C7 . . 129.01(12) ?
O2 C6 C5 . . 124.93(10) ?
C7 C6 C5 . . 106.05(9) ?
C6 C5 C4 . . 108.00(9) ?
C6 C5 H5A . . 110.1 ?
C4 C5 H5A . . 110.1 ?
C6 C5 H5B . . 110.1 ?
C4 C5 H5B . . 110.1 ?
H5A C5 H5B . . 108.4 ?

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
O1 C1 C2 C3 . . . . -178.64(12) ?
O1 C1 C2 N1 . . . . 1.2(2) ?
C3 C2 N1 C8 . . . . -0.24(12) ?
C1 C2 N1 C8 . . . . 179.85(10) ?
C2 N1 C8 C7 . . . . 0.31(12) ?
C2 N1 C8 C9 . . . . 179.47(10) ?
C10 C9 C8 N1 . . . . -116.82(12) ?
C10 C9 C8 C7 . . . . 62.10(17) ?
N1 C8 C7 C3 . . . . -0.26(12) ?
C9 C8 C7 C3 . . . . -179.33(11) ?
N1 C8 C7 C6 . . . . -178.72(13) ?
C9 C8 C7 C6 . . . . 2.2(2) ?
N1 C2 C3 C7 . . . . 0.06(12) ?
C1 C2 C3 C7 . . . . 179.96(12) ?
N1 C2 C3 C4 . . . . 179.71(13) ?
C1 C2 C3 C4 . . . . -0.4(2) ?
C8 C7 C3 C2 . . . . 0.12(12) ?
C6 C7 C3 C2 . . . . 179.08(9) ?
C8 C7 C3 C4 . . . . -179.63(9) ?
C6 C7 C3 C4 . . . . -0.67(13) ?
C2 C3 C4 C5 . . . . 177.97(13) ?
C7 C3 C4 C5 . . . . -2.39(13) ?
C3 C7 C6 O2 . . . . -176.23(12) ?
C8 C7 C6 O2 . . . . 2.2(2) ?
C3 C7 C6 C5 . . . . 3.51(13) ?
C8 C7 C6 C5 . . . . -178.05(13) ?
O2 C6 C5 C4 . . . . 174.82(12) ?
C7 C6 C5 C4 . . . . -4.94(13) ?
C3 C4 C5 C6 . . . . 4.41(13) ?



