# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 2144817'
loop_
_audit_author_name
_audit_author_address
'Hao Lei'
;Jinan University
China
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;
_audit_creation_date             2021-12-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H15 N O3'
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   14.3468(7)
_cell_length_b                   6.9678(4)
_cell_length_c                   12.0645(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1206.04(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1937
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7200
_cell_measurement_theta_min      4.7660
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3472
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.132
_diffrn_reflns_theta_min         4.789
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  -8.00   0.50    0.50    --    0.00 -38.00 120.00   94
  2  ω    -87.00 -52.00   0.50    0.50    --    0.00 -38.00-150.00   70
  3  ω    -28.00  11.00   0.50    0.50    --    0.00 -38.00-150.00   78
  4  ω     19.00 108.00   0.50    1.50    --   95.20 -30.00 -30.00  178
  5  ω     72.00 131.00   0.50    1.50    --   95.20  61.00-180.00  118
  6  ω     87.00 119.00   0.50    1.50    --   95.20 -77.00 120.00   64
  7  ω     13.00  74.00   0.50    1.50    --   95.20 -77.00 120.00  122
  8  ω     67.00  93.00   0.50    1.50    --   95.20 -82.00 -90.00   52
  9  ω     12.00  49.00   0.50    1.50    --   95.20 -82.00 -90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0224140000
_diffrn_orient_matrix_UB_12      0.0601672000
_diffrn_orient_matrix_UB_13      -0.1199102000
_diffrn_orient_matrix_UB_21      0.0969148000
_diffrn_orient_matrix_UB_22      0.0936345000
_diffrn_orient_matrix_UB_23      -0.0102158000
_diffrn_orient_matrix_UB_31      0.0404374000
_diffrn_orient_matrix_UB_32      -0.1911710000
_diffrn_orient_matrix_UB_33      -0.0425061000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1148
_reflns_number_total             1291
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.133
_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)+(0.1116P)²+0.8780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2100
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H12B(0.5) H12C(0.5)
3.a Riding coordinates:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.39857(17) 0.750000 0.2213(2) 0.0509(8) Uani 1 2 d S T P . .
O2 O 0.75002(17) 0.750000 0.7586(2) 0.0521(7) Uani 1 2 d S T P . .
O3 O 0.59534(17) 0.750000 0.78633(18) 0.0425(7) Uani 1 2 d S T P . .
N1 N 0.45077(17) 0.750000 0.4013(2) 0.0306(6) Uani 1 2 d S T P . .
C1 C 0.4619(2) 0.750000 0.2885(3) 0.0349(7) Uani 1 2 d S T P . .
C2 C 0.5664(2) 0.750000 0.2623(3) 0.0332(7) Uani 1 2 d S T P . .
C3 C 0.6089(2) 0.750000 0.3767(3) 0.0307(7) Uani 1 2 d S T P . .
C4 C 0.7008(2) 0.750000 0.4115(3) 0.0337(7) Uani 1 2 d S T P . .
H4 H 0.749092 0.750000 0.360093 0.040 Uiso 1 2 calc R U P . .
C5 C 0.7197(2) 0.750000 0.5248(3) 0.0334(7) Uani 1 2 d S T P . .
H5 H 0.781261 0.750000 0.549017 0.040 Uiso 1 2 calc R U P . .
C6 C 0.6472(2) 0.750000 0.6027(3) 0.0307(7) Uani 1 2 d S T P . .
C7 C 0.5542(2) 0.750000 0.5677(2) 0.0292(7) Uani 1 2 d S T P . .
H7 H 0.505533 0.750000 0.618563 0.035 Uiso 1 2 calc R U P . .
C8 C 0.53733(19) 0.750000 0.4551(2) 0.0280(7) Uani 1 2 d S T P . .
C9 C 0.59122(17) 0.5693(4) 0.19588(19) 0.0421(6) Uani 1 1 d . . . . .
H9A H 0.576321 0.457437 0.238784 0.063 Uiso 1 1 calc R U . . .
H9B H 0.656646 0.569808 0.179212 0.063 Uiso 1 1 calc R U . . .
H9C H 0.556196 0.567719 0.128081 0.063 Uiso 1 1 calc R U . . .
C10 C 0.3618(2) 0.750000 0.4588(3) 0.0355(7) Uani 1 2 d S T P . .
H10A H 0.327203 0.862490 0.438300 0.053 Uiso 0.5 1 d R U P A -1
H10B H 0.327203 0.637510 0.438300 0.053 Uiso 0.5 1 d R U P A -1
H10C H 0.372053 0.750000 0.537390 0.053 Uiso 0.5 1 d R U P A -1
C11 C 0.6715(2) 0.750000 0.7224(3) 0.0358(8) Uani 1 2 d S T P . .
C12 C 0.6134(3) 0.750000 0.9044(3) 0.0603(12) Uani 1 2 d S T P . .
H12A H 0.679455 0.750000 0.917387 0.090 Uiso 0.5 1 d R U P B -1
H12B H 0.586275 0.862490 0.937017 0.090 Uiso 0.5 1 d R U P B -1
H12C H 0.586275 0.637510 0.937017 0.090 Uiso 0.5 1 d R U P B -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.218(4) . ?
O2 C11 1.208(4) . ?
O3 C11 1.337(4) . ?
O3 C12 1.447(4) . ?
N1 C1 1.370(4) . ?
N1 C8 1.401(4) . ?
N1 C10 1.453(4) . ?
C1 C2 1.532(4) . ?
C2 C3 1.509(4) . ?
C2 C9 1.534(3) 7_575 ?
C2 C9 1.534(3) . ?
C3 C4 1.383(4) . ?
C3 C8 1.396(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(4) . ?
C6 C7 1.399(4) . ?
C6 C11 1.486(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 O3 C12 114.9(3) . . ?
C1 N1 C8 110.9(2) . . ?
C1 N1 C10 125.2(3) . . ?
C8 N1 C10 123.9(3) . . ?
O1 C1 N1 125.0(3) . . ?
O1 C1 C2 126.3(3) . . ?
N1 C1 C2 108.6(3) . . ?
C1 C2 C9 109.55(18) . . ?
C1 C2 C9 109.55(18) . 7_575 ?
C3 C2 C1 101.9(2) . . ?
C3 C2 C9 112.60(17) . 7_575 ?
C3 C2 C9 112.60(17) . . ?
C9 C2 C9 110.3(3) . 7_575 ?
C4 C3 C2 131.5(3) . . ?
C4 C3 C8 119.7(3) . . ?
C8 C3 C2 108.8(3) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 118.9(3) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C11 118.5(3) . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 C11 121.1(3) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 C6 117.7(3) . . ?
C8 C7 H7 121.2 . . ?
C3 C8 N1 109.8(3) . . ?
C7 C8 N1 127.7(3) . . ?
C7 C8 C3 122.5(3) . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.4 . . ?
N1 C10 H10B 109.4 . . ?
N1 C10 H10C 109.7 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O3 123.6(3) . . ?
O2 C11 C6 124.7(3) . . ?
O3 C11 C6 111.7(3) . . ?
O3 C12 H12A 109.8 . . ?
O3 C12 H12B 109.3 . . ?
O3 C12 H12C 109.3 . . ?
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 C1 C2 C3 180.000(0) . . . . ?
O1 C1 C2 C9 60.56(17) . . . 7_575 ?
O1 C1 C2 C9 -60.56(17) . . . . ?
N1 C1 C2 C3 0.000(0) . . . . ?
N1 C1 C2 C9 -119.44(17) . . . 7_575 ?
N1 C1 C2 C9 119.44(17) . . . . ?
C1 N1 C8 C3 0.000(0) . . . . ?
C1 N1 C8 C7 180.000(0) . . . . ?
C1 C2 C3 C4 180.000(0) . . . . ?
C1 C2 C3 C8 0.000(0) . . . . ?
C2 C3 C4 C5 180.000(0) . . . . ?
C2 C3 C8 N1 0.000(0) . . . . ?
C2 C3 C8 C7 180.000(0) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C4 C3 C8 N1 180.000(0) . . . . ?
C4 C3 C8 C7 0.000(1) . . . . ?
C4 C5 C6 C7 0.000(1) . . . . ?
C4 C5 C6 C11 180.000(1) . . . . ?
C5 C6 C7 C8 0.000(1) . . . . ?
C5 C6 C11 O2 0.000(1) . . . . ?
C5 C6 C11 O3 180.000(0) . . . . ?
C6 C7 C8 N1 180.000(0) . . . . ?
C6 C7 C8 C3 0.000(1) . . . . ?
C7 C6 C11 O2 180.000(1) . . . . ?
C7 C6 C11 O3 0.000(1) . . . . ?
C8 N1 C1 O1 180.000(0) . . . . ?
C8 N1 C1 C2 0.000(0) . . . . ?
C8 C3 C4 C5 0.000(1) . . . . ?
C9 C2 C3 C4 62.73(19) . . . . ?
C9 C2 C3 C4 -62.73(19) 7_575 . . . ?
C9 C2 C3 C8 117.27(19) 7_575 . . . ?
C9 C2 C3 C8 -117.27(19) . . . . ?
C10 N1 C1 O1 0.000(0) . . . . ?
C10 N1 C1 C2 180.000(0) . . . . ?
C10 N1 C8 C3 180.000(0) . . . . ?
C10 N1 C8 C7 0.000(1) . . . . ?
C11 C6 C7 C8 180.000(1) . . . . ?
C12 O3 C11 O2 0.000(1) . . . . ?
C12 O3 C11 C6 180.000(1) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.229
_oxdiff_exptl_absorpt_empirical_full_min 0.442
