# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2305770'
loop_
_audit_author_name
_audit_author_address
'Yan Wang'
;ningxia university
China
;
_audit_update_record             
;
2023-11-05 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N O3'
_chemical_formula_weight         195.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   12.712(3)
_cell_length_b                   5.7373(15)
_cell_length_c                   15.256(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.177(5)
_cell_angle_gamma                90
_cell_volume                     1030.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2162
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      18.52

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21880
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_av_R_equivalents  0.1467
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.746
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1812
_reflns_number_gt                798
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1071P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1812
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1652
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.2100
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.1965(4) 0.5137(8) 0.7522(3) 0.0926(13) Uani 1 1 d . . . . .
H1 H 0.2250 0.3953 0.7965 0.111 Uiso 1 1 calc R U . . .
C2 C 0.2180(3) 0.5034(7) 0.6704(3) 0.0816(12) Uani 1 1 d . . . . .
H2 H 0.2598 0.3802 0.6606 0.098 Uiso 1 1 calc R U . . .
C3 C 0.1776(3) 0.6749(6) 0.6032(2) 0.0592(9) Uani 1 1 d . . . . .
C4 C 0.1177(3) 0.8509(6) 0.6230(2) 0.0670(10) Uani 1 1 d . . . . .
H4 H 0.0896 0.9728 0.5804 0.080 Uiso 1 1 calc R U . . .
C5 C 0.0988(3) 0.8479(8) 0.7061(3) 0.0798(12) Uani 1 1 d . . . . .
H5 H 0.0565 0.9687 0.7171 0.096 Uiso 1 1 calc R U . . .
C6 C 0.1994(3) 0.6713(6) 0.5125(2) 0.0631(10) Uani 1 1 d . . . . .
C7 C 0.1848(4) 0.4301(7) 0.4693(3) 0.0864(12) Uani 1 1 d . . . . .
H7A H 0.2399 0.3265 0.5118 0.130 Uiso 1 1 calc R U . . .
H7B H 0.1956 0.4369 0.4103 0.130 Uiso 1 1 calc R U . . .
H7C H 0.1098 0.3739 0.4582 0.130 Uiso 1 1 calc R U . . .
C8 C 0.3199(3) 0.7568(8) 0.5338(3) 0.0736(11) Uani 1 1 d . . . . .
C9 C 0.5162(3) 0.6755(8) 0.6159(3) 0.0953(13) Uani 1 1 d . . . . .
H9A H 0.5332 0.8219 0.6502 0.114 Uiso 1 1 calc R U . . .
H9B H 0.5345 0.6905 0.5599 0.114 Uiso 1 1 calc R U . . .
C10 C 0.5813(4) 0.4856(10) 0.6759(4) 0.1305(18) Uani 1 1 d . . . . .
H10A H 0.5605 0.3408 0.6422 0.196 Uiso 1 1 calc R U . . .
H10B H 0.5652 0.4781 0.7324 0.196 Uiso 1 1 calc R U . . .
H10C H 0.6610 0.5131 0.6924 0.196 Uiso 1 1 calc R U . . .
N1 N 0.1374(3) 0.6832(7) 0.7714(2) 0.0818(10) Uani 1 1 d . . . . .
O1 O 0.1218(2) 0.8293(4) 0.45032(16) 0.0785(8) Uani 1 1 d . . . . .
H1A H 0.1314 0.8334 0.4001 0.118 Uiso 1 1 calc R U . . .
O2 O 0.3431(2) 0.9275(6) 0.5003(3) 0.1189(12) Uani 1 1 d . . . . .
O3 O 0.3970(2) 0.6156(5) 0.58967(19) 0.0891(9) 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
C1 N1 1.328(5) . ?
C1 C2 1.376(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(4) . ?
C3 C6 1.510(5) . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.326(5) . ?
C5 H5 0.9300 . ?
C6 O1 1.410(4) . ?
C6 C7 1.514(5) . ?
C6 C8 1.522(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O2 1.192(4) . ?
C8 O3 1.309(4) . ?
C9 O3 1.455(4) . ?
C9 C10 1.462(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O1 H1A 0.8200 . ?

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
N1 C1 C2 123.7(4) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 116.5(3) . . ?
C4 C3 C6 121.6(3) . . ?
C2 C3 C6 121.9(3) . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 123.9(4) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
O1 C6 C3 106.5(3) . . ?
O1 C6 C7 110.8(3) . . ?
C3 C6 C7 112.1(3) . . ?
O1 C6 C8 109.2(3) . . ?
C3 C6 C8 108.5(3) . . ?
C7 C6 C8 109.6(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 O3 122.8(4) . . ?
O2 C8 C6 124.4(4) . . ?
O3 C8 C6 112.7(3) . . ?
O3 C9 C10 106.3(4) . . ?
O3 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
O3 C9 H9B 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
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 . . ?
C5 N1 C1 115.8(3) . . ?
C6 O1 H1A 109.5 . . ?
C8 O3 C9 118.7(3) . . ?

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 C2 C3 0.1(6) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C1 C2 C3 C6 179.8(3) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C6 C3 C4 C5 179.6(3) . . . . ?
C3 C4 C5 N1 1.2(6) . . . . ?
C4 C3 C6 O1 -16.8(4) . . . . ?
C2 C3 C6 O1 164.0(3) . . . . ?
C4 C3 C6 C7 -138.2(3) . . . . ?
C2 C3 C6 C7 42.6(4) . . . . ?
C4 C3 C6 C8 100.6(4) . . . . ?
C2 C3 C6 C8 -78.6(4) . . . . ?
O1 C6 C8 O2 -2.0(5) . . . . ?
C3 C6 C8 O2 -117.7(4) . . . . ?
C7 C6 C8 O2 119.6(4) . . . . ?
O1 C6 C8 O3 -178.6(3) . . . . ?
C3 C6 C8 O3 65.8(4) . . . . ?
C7 C6 C8 O3 -57.0(4) . . . . ?
C4 C5 N1 C1 -0.5(6) . . . . ?
C2 C1 N1 C5 -0.1(6) . . . . ?
O2 C8 O3 C9 3.3(6) . . . . ?
C6 C8 O3 C9 179.9(3) . . . . ?
C10 C9 O3 C8 -178.7(4) . . . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.041



