# 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 2353681'
loop_
_audit_author_name
_audit_author_address
'Xiyan Duan'
;Henan University of Science and Technology
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;
_audit_creation_date             2024-04-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H17 N O3'
_chemical_formula_sum            'C12 H17 N O3'
_chemical_formula_weight         223.26
_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                   6.995(3)
_cell_length_b                   11.544(5)
_cell_length_c                   14.861(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.400(9)
_cell_angle_gamma                90
_cell_volume                     1183.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2219
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.83
_cell_measurement_theta_min      3.44
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6728
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0825 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.9028.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13003
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.245
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1172
_reflns_number_total             2064
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2064
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.069
_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)+(0.0892P)²+0.3969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1940
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), N1(H1)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), 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
C1 C -0.0329(6) 0.3598(4) 0.6345(3) 0.0773(13) Uani 1 1 d . . . . .
H1A H -0.1723 0.3490 0.6244 0.093 Uiso 1 1 calc R U . . .
H1B H 0.0213 0.3160 0.6883 0.093 Uiso 1 1 calc R U . . .
C2 C 0.0488(5) 0.3133(3) 0.5524(3) 0.0754(12) Uani 1 1 d . . . . .
H2A H 0.0223 0.2309 0.5459 0.090 Uiso 1 1 calc R U . . .
H2B H -0.0144 0.3517 0.4974 0.090 Uiso 1 1 calc R U . . .
C3 C 0.2655(5) 0.3336(3) 0.5640(2) 0.0531(9) Uani 1 1 d . . . . .
H3 H 0.3258 0.2872 0.6162 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3093(5) 0.4588(4) 0.5871(3) 0.0713(12) Uani 1 1 d . . . . .
H4A H 0.2632 0.5066 0.5343 0.086 Uiso 1 1 calc R U . . .
H4B H 0.4484 0.4693 0.6027 0.086 Uiso 1 1 calc R U . . .
C5 C 0.2124(5) 0.4973(4) 0.6671(3) 0.0759(13) Uani 1 1 d . . . . .
H5A H 0.2681 0.4546 0.7213 0.091 Uiso 1 1 calc R U . . .
H5B H 0.2380 0.5790 0.6787 0.091 Uiso 1 1 calc R U . . .
C6 C 0.3518(4) 0.2949(3) 0.4824(2) 0.0457(8) Uani 1 1 d . . . . .
C7 C 0.4995(4) 0.2170(3) 0.4735(2) 0.0434(8) Uani 1 1 d . . . . .
C8 C 0.5248(4) 0.2186(3) 0.3789(2) 0.0459(8) Uani 1 1 d . . . . .
C9 C 0.3930(5) 0.2944(3) 0.3359(2) 0.0507(9) Uani 1 1 d . . . . .
H9 H 0.3755 0.3124 0.2741 0.061 Uiso 1 1 calc R U . . .
C10 C 0.6655(5) 0.1505(3) 0.3327(2) 0.0635(10) Uani 1 1 d . . . . .
H10A H 0.7955 0.1671 0.3616 0.095 Uiso 1 1 calc R U . . .
H10B H 0.6500 0.1719 0.2695 0.095 Uiso 1 1 calc R U . . .
H10C H 0.6403 0.0692 0.3377 0.095 Uiso 1 1 calc R U . . .
C11 C 0.6001(5) 0.1479(3) 0.5486(2) 0.0467(8) Uani 1 1 d . . . . .
C12 C 0.8442(5) 0.0069(3) 0.5929(3) 0.0645(11) Uani 1 1 d . . . . .
H12A H 0.9342 -0.0404 0.5670 0.097 Uiso 1 1 calc R U . . .
H12B H 0.7583 -0.0418 0.6202 0.097 Uiso 1 1 calc R U . . .
H12C H 0.9141 0.0567 0.6386 0.097 Uiso 1 1 calc R U . . .
N1 N 0.2889(4) 0.3407(2) 0.39842(18) 0.0516(8) Uani 1 1 d . . . . .
H1 H 0.1977 0.3910 0.3862 0.062 Uiso 1 1 calc R U . . .
O1 O 0.0097(3) 0.4789(2) 0.64977(15) 0.0571(7) Uani 1 1 d . . . . .
O2 O 0.5751(4) 0.1511(2) 0.62707(16) 0.0712(8) Uani 1 1 d . . . . .
O3 O 0.7332(3) 0.0764(2) 0.52215(15) 0.0556(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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.527(5) . ?
C1 O1 1.417(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.516(5) . ?
C3 H3 0.9800 . ?
C3 C4 1.505(5) . ?
C3 C6 1.507(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.528(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 O1 1.415(4) . ?
C6 C7 1.392(4) . ?
C6 N1 1.361(4) . ?
C7 C8 1.446(4) . ?
C7 C11 1.457(4) . ?
C8 C9 1.354(5) . ?
C8 C10 1.509(4) . ?
C9 H9 0.9300 . ?
C9 N1 1.379(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O2 1.207(4) . ?
C11 O3 1.349(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 O3 1.445(4) . ?
N1 H1 0.8600 . ?

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
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
O1 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
O1 C1 C2 111.9(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.7(3) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C2 C3 H3 107.4 . . ?
C4 C3 C2 109.7(3) . . ?
C4 C3 H3 107.4 . . ?
C4 C3 C6 112.0(3) . . ?
C6 C3 C2 112.8(3) . . ?
C6 C3 H3 107.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 C5 110.9(3) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O1 C5 C4 111.9(3) . . ?
O1 C5 H5A 109.2 . . ?
O1 C5 H5B 109.2 . . ?
C7 C6 C3 132.0(3) . . ?
N1 C6 C3 120.7(3) . . ?
N1 C6 C7 107.3(3) . . ?
C6 C7 C8 107.2(3) . . ?
C6 C7 C11 123.7(3) . . ?
C8 C7 C11 129.1(3) . . ?
C7 C8 C10 129.0(3) . . ?
C9 C8 C7 106.5(3) . . ?
C9 C8 C10 124.5(3) . . ?
C8 C9 H9 125.5 . . ?
C8 C9 N1 109.0(3) . . ?
N1 C9 H9 125.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C7 126.5(3) . . ?
O2 C11 O3 121.1(3) . . ?
O3 C11 C7 112.4(3) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
C6 N1 C9 109.9(3) . . ?
C6 N1 H1 125.0 . . ?
C9 N1 H1 125.0 . . ?
C5 O1 C1 110.7(3) . . ?
C11 O3 C12 116.2(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
C1 C2 C3 C4 -51.4(4) . . . . ?
C1 C2 C3 C6 -176.9(3) . . . . ?
C2 C1 O1 C5 -60.4(4) . . . . ?
C2 C3 C4 C5 51.3(4) . . . . ?
C2 C3 C6 C7 -123.1(4) . . . . ?
C2 C3 C6 N1 58.9(4) . . . . ?
C3 C4 C5 O1 -56.4(5) . . . . ?
C3 C6 C7 C8 -177.6(3) . . . . ?
C3 C6 C7 C11 3.6(6) . . . . ?
C3 C6 N1 C9 178.2(3) . . . . ?
C4 C3 C6 C7 112.6(4) . . . . ?
C4 C3 C6 N1 -65.4(4) . . . . ?
C4 C5 O1 C1 60.2(5) . . . . ?
C6 C3 C4 C5 177.3(3) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C6 C7 C8 C10 180.0(3) . . . . ?
C6 C7 C11 O2 -2.7(5) . . . . ?
C6 C7 C11 O3 178.1(3) . . . . ?
C7 C6 N1 C9 -0.2(4) . . . . ?
C7 C8 C9 N1 0.6(4) . . . . ?
C7 C11 O3 C12 178.2(3) . . . . ?
C8 C7 C11 O2 178.9(3) . . . . ?
C8 C7 C11 O3 -0.4(5) . . . . ?
C8 C9 N1 C6 -0.2(4) . . . . ?
C10 C8 C9 N1 179.9(3) . . . . ?
C11 C7 C8 C9 178.0(3) . . . . ?
C11 C7 C8 C10 -1.4(6) . . . . ?
N1 C6 C7 C8 0.5(4) . . . . ?
N1 C6 C7 C11 -178.2(3) . . . . ?
O1 C1 C2 C3 56.4(5) . . . . ?
O2 C11 O3 C12 -1.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
