# Electronic Supplementary Material (ESI) 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. 
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data_yb6
_database_code_depnum_ccdc_archive 'CCDC 2296410'
loop_
_audit_author_name
_audit_author_address
BiaoYao
;South China University of Technology
China
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2023-09-21
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N O3'
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23
_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 0.0033 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'

_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                   25.4531(15)
_cell_length_b                   5.4653(3)
_cell_length_c                   7.6438(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.309(2)
_cell_angle_gamma                90
_cell_volume                     1058.76(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2188
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.245
_cell_measurement_theta_min      3.215
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1030 before and 0.0772 after correction.
The Ratio of minimum to maximum transmission is 0.6941.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9339
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_min         2.411
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1518
_reflns_number_total             2123
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.088
_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)+(0.0289P)²+0.6952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1236
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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
O2 O 0.38514(6) 0.3694(3) 0.6784(2) 0.0248(4) Uani 1 1 d . . . . .
O1 O 0.28931(6) 0.1903(3) 0.5342(2) 0.0273(4) Uani 1 1 d . . . . .
O3 O 0.41899(7) 0.6172(3) 0.8948(2) 0.0304(4) Uani 1 1 d . . . . .
N1 N 0.23364(7) 0.1945(3) 0.5222(3) 0.0243(5) Uani 1 1 d . . . . .
C11 C 0.42118(9) 0.4306(4) 0.8106(3) 0.0232(5) Uani 1 1 d . . . . .
C6 C 0.12272(10) 0.2851(4) 0.4757(3) 0.0246(5) Uani 1 1 d . . . . .
H6 H 0.133817 0.141244 0.538439 0.029 Uiso 1 1 calc R U . . .
C7 C 0.21693(9) 0.4034(4) 0.4624(3) 0.0216(5) Uani 1 1 d . . . . .
C5 C 0.06969(9) 0.3275(4) 0.4327(3) 0.0242(5) Uani 1 1 d . . . . .
H5 H 0.044459 0.212266 0.465682 0.029 Uiso 1 1 calc R U . . .
C1 C 0.16024(9) 0.4530(4) 0.4274(3) 0.0223(5) Uani 1 1 d . . . . .
C9 C 0.30933(9) 0.4303(4) 0.4843(3) 0.0238(5) Uani 1 1 d . . . . .
H9 H 0.331729 0.410389 0.384482 0.029 Uiso 1 1 calc R U . . .
C2 C 0.14315(9) 0.6660(4) 0.3386(3) 0.0243(5) Uani 1 1 d . . . . .
H2 H 0.168215 0.783682 0.308139 0.029 Uiso 1 1 calc R U . . .
C8 C 0.25997(9) 0.5775(4) 0.4235(3) 0.0225(5) Uani 1 1 d . . . . .
H8A H 0.258157 0.731423 0.490962 0.027 Uiso 1 1 calc R U . . .
H8B H 0.258475 0.615893 0.296611 0.027 Uiso 1 1 calc R U . . .
C4 C 0.05281(9) 0.5383(4) 0.3411(3) 0.0255(5) Uani 1 1 d . . . . .
H4 H 0.016247 0.566084 0.310824 0.031 Uiso 1 1 calc R U . . .
C10 C 0.34172(9) 0.5370(4) 0.6397(3) 0.0233(5) Uani 1 1 d . . . . .
H10A H 0.354888 0.701440 0.611325 0.028 Uiso 1 1 calc R U . . .
H10B H 0.320474 0.551253 0.741362 0.028 Uiso 1 1 calc R U . . .
C3 C 0.08961(10) 0.7066(4) 0.2946(3) 0.0261(5) Uani 1 1 d . . . . .
H3 H 0.078290 0.850448 0.232318 0.031 Uiso 1 1 calc R U . . .
C12 C 0.46194(9) 0.2347(4) 0.8388(3) 0.0269(6) Uani 1 1 d . . . . .
H12A H 0.446442 0.090854 0.890802 0.040 Uiso 1 1 calc R U . . .
H12B H 0.491563 0.294822 0.918230 0.040 Uiso 1 1 calc R U . . .
H12C H 0.474583 0.189684 0.725883 0.040 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
O2 C11 1.343(3) . ?
O2 C10 1.445(3) . ?
O1 N1 1.412(2) . ?
O1 C9 1.470(3) . ?
O3 C11 1.210(3) . ?
N1 C7 1.287(3) . ?
C11 C12 1.493(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.379(3) . ?
C6 C1 1.399(3) . ?
C7 C1 1.468(3) . ?
C7 C8 1.501(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.396(3) . ?
C1 C2 1.396(3) . ?
C9 H9 1.0000 . ?
C9 C8 1.527(3) . ?
C9 C10 1.500(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C3 1.382(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C3 H3 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C11 O2 C10 116.91(17) . . ?
N1 O1 C9 109.81(15) . . ?
C7 N1 O1 109.50(18) . . ?
O2 C11 C12 110.32(19) . . ?
O3 C11 O2 123.2(2) . . ?
O3 C11 C12 126.4(2) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C1 120.3(2) . . ?
C1 C6 H6 119.9 . . ?
N1 C7 C1 121.0(2) . . ?
N1 C7 C8 114.2(2) . . ?
C1 C7 C8 124.72(19) . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C1 C7 120.9(2) . . ?
C2 C1 C6 119.1(2) . . ?
C2 C1 C7 120.0(2) . . ?
O1 C9 H9 109.6 . . ?
O1 C9 C8 104.69(17) . . ?
O1 C9 C10 108.67(18) . . ?
C8 C9 H9 109.6 . . ?
C10 C9 H9 109.6 . . ?
C10 C9 C8 114.37(19) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C7 C8 C9 101.59(17) . . ?
C7 C8 H8A 111.5 . . ?
C7 C8 H8B 111.5 . . ?
C9 C8 H8A 111.5 . . ?
C9 C8 H8B 111.5 . . ?
H8A C8 H8B 109.3 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
O2 C10 C9 105.64(17) . . ?
O2 C10 H10A 110.6 . . ?
O2 C10 H10B 110.6 . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O1 N1 C7 C1 176.55(19) . . . . ?
O1 N1 C7 C8 0.0(3) . . . . ?
O1 C9 C8 C7 4.7(2) . . . . ?
O1 C9 C10 O2 62.0(2) . . . . ?
N1 O1 C9 C8 -5.1(2) . . . . ?
N1 O1 C9 C10 117.49(19) . . . . ?
N1 C7 C1 C6 7.0(3) . . . . ?
N1 C7 C1 C2 -170.5(2) . . . . ?
N1 C7 C8 C9 -3.1(3) . . . . ?
C11 O2 C10 C9 177.75(18) . . . . ?
C6 C5 C4 C3 -0.5(3) . . . . ?
C6 C1 C2 C3 -1.9(3) . . . . ?
C7 C1 C2 C3 175.7(2) . . . . ?
C5 C6 C1 C7 -176.2(2) . . . . ?
C5 C6 C1 C2 1.4(3) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C1 C6 C5 C4 -0.2(3) . . . . ?
C1 C7 C8 C9 -179.5(2) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C9 O1 N1 C7 3.4(2) . . . . ?
C8 C7 C1 C6 -176.8(2) . . . . ?
C8 C7 C1 C2 5.7(3) . . . . ?
C8 C9 C10 O2 178.55(17) . . . . ?
C10 O2 C11 O3 -0.9(3) . . . . ?
C10 O2 C11 C12 177.57(18) . . . . ?
C10 C9 C8 C7 -114.1(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
