# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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 
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data_201120c_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2132509'
loop_
_audit_author_name
_audit_author_address
ShaoRui
;AnHui Normal University
China
;
_audit_update_record             
;
2022-01-05 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2020-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 N2 O3'
_chemical_formula_sum            'C12 H12 N2 O3'
_chemical_formula_weight         232.24
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.8038(11)
_cell_length_b                   8.8160(15)
_cell_length_c                   19.236(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.296(2)
_cell_angle_gamma                90
_cell_volume                     1144.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2342
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.363
_cell_measurement_theta_min      2.545
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1014 before and 0.0602 after correction. The Ratio of minimum to maximum transmission is 0.8444. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.865
_diffrn_reflns_theta_min         2.135
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1589
_reflns_number_total             2701
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.034
_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)+(0.0752P)²+0.3925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1755
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C7(H7), C2(H2A), C5(H5), C3(H3), C4(H4)
2.c 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
O3 O 0.2495(2) 0.9914(2) 0.49546(10) 0.0552(6) Uani 1 1 d . . . . .
O2 O 0.7192(2) 0.4911(2) 0.60221(9) 0.0495(5) Uani 1 1 d . . . . .
O1 O 0.7129(3) 0.6579(2) 0.51420(10) 0.0601(6) Uani 1 1 d . . . . .
N2 N 0.1028(3) 0.8534(2) 0.57245(11) 0.0417(5) Uani 1 1 d . . . . .
H2 H -0.007671 0.860566 0.545444 0.050 Uiso 1 1 calc R . . . .
N1 N 0.4450(3) 0.8344(2) 0.56619(11) 0.0447(6) Uani 1 1 d . . . . .
H1 H 0.547288 0.889589 0.562263 0.054 Uiso 1 1 calc R . . . .
C1 C 0.0882(3) 0.7984(3) 0.64059(13) 0.0370(6) Uani 1 1 d . . . . .
C9 C 0.2654(3) 0.8966(3) 0.54340(13) 0.0383(6) Uani 1 1 d . . . . .
C8 C 0.4811(3) 0.6892(3) 0.59555(13) 0.0381(6) Uani 1 1 d . . . . .
C6 C 0.2155(3) 0.6887(3) 0.67417(13) 0.0404(6) Uani 1 1 d . . . . .
C7 C 0.3818(3) 0.6248(3) 0.64285(13) 0.0405(6) Uani 1 1 d . . . . .
H7 H 0.422665 0.528118 0.657704 0.049 Uiso 1 1 calc R . . . .
C10 C 0.6486(4) 0.6123(3) 0.56543(14) 0.0412(6) Uani 1 1 d . . . . .
C2 C -0.0711(4) 0.8521(3) 0.67278(14) 0.0475(7) Uani 1 1 d . . . . .
H2A H -0.155262 0.925233 0.650493 0.057 Uiso 1 1 calc R . . . .
C11 C 0.8829(4) 0.4149(3) 0.57421(15) 0.0539(8) Uani 1 1 d . . . . .
H11A H 0.988473 0.486818 0.569745 0.065 Uiso 1 1 calc R . . . .
H11B H 0.837725 0.374033 0.528136 0.065 Uiso 1 1 calc R . . . .
C5 C 0.1754(4) 0.6349(4) 0.73926(15) 0.0584(8) Uani 1 1 d . . . . .
H5 H 0.257262 0.560921 0.761942 0.070 Uiso 1 1 calc R . . . .
C3 C -0.1044(4) 0.7967(4) 0.73805(16) 0.0606(8) Uani 1 1 d . . . . .
H3 H -0.210061 0.833480 0.759350 0.073 Uiso 1 1 calc R . . . .
C4 C 0.0179(5) 0.6884(4) 0.77094(16) 0.0665(9) Uani 1 1 d . . . . .
H4 H -0.004891 0.650892 0.814397 0.080 Uiso 1 1 calc R . . . .
C12 C 0.9568(5) 0.2916(4) 0.62208(18) 0.0749(10) Uani 1 1 d . . . . .
H12A H 1.002091 0.332862 0.667465 0.112 Uiso 1 1 calc GR . . . .
H12B H 1.064491 0.240920 0.604035 0.112 Uiso 1 1 calc GR . . . .
H12C H 0.851899 0.220400 0.625955 0.112 Uiso 1 1 calc GR . . . .


_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
O3 C9 1.240(3) . ?
O2 C10 1.336(3) . ?
O2 C11 1.460(3) . ?
O1 C10 1.198(3) . ?
N2 H2 0.8600 . ?
N2 C1 1.413(3) . ?
N2 C9 1.356(3) . ?
N1 H1 0.8600 . ?
N1 C9 1.360(3) . ?
N1 C8 1.408(3) . ?
C1 C6 1.400(3) . ?
C1 C2 1.398(3) . ?
C8 C7 1.328(3) . ?
C8 C10 1.504(4) . ?
C6 C7 1.461(3) . ?
C6 C5 1.398(4) . ?
C7 H7 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C3 1.392(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.472(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(4) . ?
C4 H4 0.9300 . ?
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
C10 O2 C11 114.3(2) . . ?
C1 N2 H2 115.3 . . ?
C9 N2 H2 115.3 . . ?
C9 N2 C1 129.5(2) . . ?
C9 N1 H1 116.6 . . ?
C9 N1 C8 126.8(2) . . ?
C8 N1 H1 116.6 . . ?
C6 C1 N2 123.6(2) . . ?
C2 C1 N2 116.4(2) . . ?
C2 C1 C6 119.9(2) . . ?
O3 C9 N2 119.8(2) . . ?
O3 C9 N1 120.1(2) . . ?
N2 C9 N1 120.1(2) . . ?
N1 C8 C10 111.0(2) . . ?
C7 C8 N1 125.8(2) . . ?
C7 C8 C10 123.2(2) . . ?
C1 C6 C7 122.8(2) . . ?
C5 C6 C1 117.9(2) . . ?
C5 C6 C7 119.2(2) . . ?
C8 C7 C6 127.3(2) . . ?
C8 C7 H7 116.4 . . ?
C6 C7 H7 116.4 . . ?
O2 C10 C8 113.3(2) . . ?
O1 C10 O2 124.1(2) . . ?
O1 C10 C8 122.6(2) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2A 119.8 . . ?
O2 C11 H11A 109.9 . . ?
O2 C11 H11B 109.9 . . ?
O2 C11 C12 109.0(2) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
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
N2 C1 C6 C7 2.6(4) . . . . ?
N2 C1 C6 C5 -174.9(2) . . . . ?
N2 C1 C2 C3 175.9(2) . . . . ?
N1 C8 C7 C6 0.3(4) . . . . ?
N1 C8 C10 O2 165.4(2) . . . . ?
N1 C8 C10 O1 -13.4(3) . . . . ?
C1 N2 C9 O3 -152.9(3) . . . . ?
C1 N2 C9 N1 28.0(4) . . . . ?
C1 C6 C7 C8 25.9(4) . . . . ?
C1 C6 C5 C4 -1.0(4) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C9 N2 C1 C6 -44.7(4) . . . . ?
C9 N2 C1 C2 139.3(3) . . . . ?
C9 N1 C8 C7 -43.3(4) . . . . ?
C9 N1 C8 C10 135.9(3) . . . . ?
C8 N1 C9 O3 -151.0(3) . . . . ?
C8 N1 C9 N2 28.2(4) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C6 C5 C4 C3 0.3(5) . . . . ?
C7 C8 C10 O2 -15.4(4) . . . . ?
C7 C8 C10 O1 165.8(3) . . . . ?
C7 C6 C5 C4 -178.6(3) . . . . ?
C10 O2 C11 C12 175.7(3) . . . . ?
C10 C8 C7 C6 -178.8(2) . . . . ?
C2 C1 C6 C7 178.4(2) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C11 O2 C10 O1 -0.9(4) . . . . ?
C11 O2 C10 C8 -179.7(2) . . . . ?
C5 C6 C7 C8 -156.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
