# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2166162'
loop_
_audit_author_name
_audit_author_address
'Guodong Yin'
;Hubei Normal University
China
;
_audit_update_record             
;
2022-10-02 deposited with the CCDC.	2023-03-08 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            'C13 H14 N2 O2'
_chemical_formula_weight         230.26

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                   9.637(8)
_cell_length_b                   11.436(9)
_cell_length_c                   11.619(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.063(18)
_cell_angle_gamma                90
_cell_volume                     1178.2(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3161
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      21.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.982
_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            17307
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.608
_diffrn_reflns_theta_max         25.065
_diffrn_reflns_theta_full        25.065
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2084
_reflns_number_gt                1058
_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)+(0.0731P)²+0.1613P] 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         2084
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1328
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1597
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.0919(3) 0.7008(2) 0.6597(3) 0.0694(8) Uani 1 1 d . . . . .
H1 H 0.0461 0.7175 0.7150 0.083 Uiso 1 1 calc R U . . .
C2 C 0.1163(3) 0.7883(2) 0.5897(3) 0.0750(8) Uani 1 1 d . . . . .
H2 H 0.0883 0.8647 0.5977 0.090 Uiso 1 1 calc R U . . .
C3 C 0.1829(3) 0.7622(3) 0.5067(3) 0.0772(8) Uani 1 1 d . . . . .
H3 H 0.1986 0.8217 0.4586 0.093 Uiso 1 1 calc R U . . .
C4 C 0.2260(3) 0.6509(2) 0.4941(2) 0.0704(8) Uani 1 1 d . . . . .
H4 H 0.2708 0.6353 0.4380 0.084 Uiso 1 1 calc R U . . .
C5 C 0.2030(3) 0.5601(2) 0.5655(2) 0.0559(7) Uani 1 1 d . . . . .
C6 C 0.1357(3) 0.5866(2) 0.6483(2) 0.0563(7) Uani 1 1 d . . . . .
C7 C 0.1121(3) 0.4948(2) 0.7230(3) 0.0637(7) Uani 1 1 d . . . . .
C8 C 0.2289(3) 0.3682(2) 0.6208(2) 0.0576(7) Uani 1 1 d . . . . .
C9 C 0.2340(3) 0.1609(2) 0.6840(3) 0.0754(8) Uani 1 1 d . . . . .
H9A H 0.1516 0.1169 0.6234 0.091 Uiso 1 1 calc R U . . .
H9B H 0.1999 0.1916 0.7462 0.091 Uiso 1 1 calc R U . . .
C10 C 0.3640(4) 0.0820(3) 0.7454(3) 0.0889(10) Uani 1 1 d . . . . .
H10A H 0.3309 0.0144 0.7784 0.107 Uiso 1 1 calc R U . . .
H10B H 0.4398 0.1225 0.8152 0.107 Uiso 1 1 calc R U . . .
C11 C 0.4331(4) 0.0417(3) 0.6563(3) 0.0866(9) Uani 1 1 d . . . . .
H11A H 0.5231 -0.0038 0.7014 0.104 Uiso 1 1 calc R U . . .
H11B H 0.3622 -0.0079 0.5925 0.104 Uiso 1 1 calc R U . . .
C12 C 0.4731(4) 0.1446(3) 0.5959(3) 0.0978(11) Uani 1 1 d . . . . .
H12A H 0.5530 0.1887 0.6589 0.117 Uiso 1 1 calc R U . . .
H12B H 0.5108 0.1171 0.5346 0.117 Uiso 1 1 calc R U . . .
C13 C 0.3416(4) 0.2226(3) 0.5336(3) 0.0886(10) Uani 1 1 d . . . . .
H13A H 0.3739 0.2916 0.5022 0.106 Uiso 1 1 calc R U . . .
H13B H 0.2671 0.1822 0.4630 0.106 Uiso 1 1 calc R U . . .
N1 N 0.2487(2) 0.44841(18) 0.55157(18) 0.0612(6) Uani 1 1 d . . . . .
N2 N 0.2739(3) 0.25770(18) 0.6210(2) 0.0689(7) Uani 1 1 d . . . . .
O1 O 0.0585(2) 0.49924(17) 0.7998(2) 0.0903(7) Uani 1 1 d . . . . .
O2 O 0.1620(2) 0.38475(14) 0.70449(16) 0.0647(6) 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 C2 1.366(4) . ?
C1 C6 1.396(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.381(3) . ?
C5 C6 1.387(3) . ?
C6 C7 1.436(4) . ?
C7 O1 1.194(3) . ?
C7 O2 1.394(3) . ?
C8 N1 1.283(3) . ?
C8 N2 1.336(3) . ?
C8 O2 1.373(3) . ?
C9 N2 1.459(3) . ?
C9 C10 1.481(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.506(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.496(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.486(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.463(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
C2 C1 C6 119.9(3) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C6 122.7(2) . . ?
N1 C5 C4 119.0(2) . . ?
C6 C5 C4 118.3(2) . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 C7 119.2(2) . . ?
C1 C6 C7 120.0(2) . . ?
O1 C7 O2 115.4(2) . . ?
O1 C7 C6 129.7(2) . . ?
O2 C7 C6 114.9(2) . . ?
N1 C8 N2 123.3(2) . . ?
N1 C8 O2 124.9(2) . . ?
N2 C8 O2 111.8(2) . . ?
N2 C9 C10 111.4(2) . . ?
N2 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 111.9(3) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 110.3(2) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 111.9(3) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N2 C13 C12 110.7(3) . . ?
N2 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C8 N1 C5 117.1(2) . . ?
C8 N2 C9 124.7(2) . . ?
C8 N2 C13 119.4(2) . . ?
C9 N2 C13 114.6(2) . . ?
C8 O2 C7 121.3(2) . . ?

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
C6 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 N1 -179.5(3) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
N1 C5 C6 C1 179.7(2) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
N1 C5 C6 C7 0.0(4) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C1 C6 C7 179.2(2) . . . . ?
C5 C6 C7 O1 179.0(3) . . . . ?
C1 C6 C7 O1 -0.7(5) . . . . ?
C5 C6 C7 O2 0.4(3) . . . . ?
C1 C6 C7 O2 -179.3(2) . . . . ?
N2 C9 C10 C11 -52.7(4) . . . . ?
C9 C10 C11 C12 54.1(4) . . . . ?
C10 C11 C12 C13 -54.9(4) . . . . ?
C11 C12 C13 N2 54.0(4) . . . . ?
N2 C8 N1 C5 -176.9(2) . . . . ?
O2 C8 N1 C5 1.9(4) . . . . ?
C6 C5 N1 C8 -1.2(4) . . . . ?
C4 C5 N1 C8 178.4(2) . . . . ?
N1 C8 N2 C9 -170.5(2) . . . . ?
O2 C8 N2 C9 10.6(4) . . . . ?
N1 C8 N2 C13 -3.7(4) . . . . ?
O2 C8 N2 C13 177.3(2) . . . . ?
C10 C9 N2 C8 -139.6(3) . . . . ?
C10 C9 N2 C13 53.1(3) . . . . ?
C12 C13 N2 C8 138.5(3) . . . . ?
C12 C13 N2 C9 -53.5(3) . . . . ?
N1 C8 O2 C7 -1.5(4) . . . . ?
N2 C8 O2 C7 177.4(2) . . . . ?
O1 C7 O2 C8 -178.6(2) . . . . ?
C6 C7 O2 C8 0.2(3) . . . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038

