# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 2068416'
loop_
_audit_author_name
_audit_author_address
'chen rongxiang'
;xinxiang university
China
;
_audit_update_record             
;
2021-03-06 deposited with the CCDC.	2021-05-25 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            'C12 H12.50 N O4'
_chemical_formula_weight         234.73

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.5895(17)
_cell_length_b                   5.0682(7)
_cell_length_c                   18.033(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.174(2)
_cell_angle_gamma                90
_cell_volume                     1149.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1776
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      26.87

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             494
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5511
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.239
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2009
_reflns_number_gt                1442
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0637P)²+0.1028P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2009
_refine_ls_number_parameters     211
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.087
_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 0.24952(13) 0.3946(3) 0.38442(10) 0.0546(5) Uani 1 1 d . . . . .
H1A H 0.1838 0.3979 0.4063 0.066 Uiso 1 1 calc R U . . .
C2 C 0.26684(16) 0.2161(4) 0.32967(11) 0.0666(5) Uani 1 1 d . . . . .
H2 H 0.2137 0.0983 0.3144 0.080 Uiso 1 1 calc R U . . .
C3 C 0.36437(16) 0.2127(4) 0.29724(11) 0.0704(6) Uani 1 1 d . . . . .
H3 H 0.3764 0.0918 0.2597 0.084 Uiso 1 1 calc R U . . .
C4 C 0.44375(15) 0.3832(4) 0.31907(10) 0.0671(6) Uani 1 1 d . . . . .
H4 H 0.5088 0.3771 0.2964 0.081 Uiso 1 1 calc R U . . .
C5 C 0.42751(12) 0.5646(3) 0.37471(10) 0.0536(5) Uani 1 1 d . . . . .
C6 C 0.32829(12) 0.5729(3) 0.40842(9) 0.0449(4) Uani 1 1 d . . . . .
C7 C 0.30903(12) 0.7579(3) 0.46792(9) 0.0498(4) Uani 1 1 d . . . . .
C8 C 0.19650(12) 0.7746(3) 0.49734(9) 0.0526(5) Uani 1 1 d D . . . .
C9 C 0.0624(3) 0.6278(10) 0.5860(3) 0.0573(11) Uani 0.587(5) 1 d D . P A 1
H9A H 0.0236 0.4655 0.5758 0.069 Uiso 0.587(5) 1 calc R U P A 1
H9B H 0.0219 0.7731 0.5643 0.069 Uiso 0.587(5) 1 calc R U P A 1
C10 C 0.0772(3) 0.6673(11) 0.6688(2) 0.0758(13) Uani 0.587(5) 1 d D . P A 1
H10 H 0.0476 0.8054 0.6950 0.091 Uiso 0.587(5) 1 calc R U P A 1
C11 C 0.2441(5) 0.4670(14) 0.6709(3) 0.0715(16) Uani 0.587(5) 1 d D . P A 1
H11A H 0.2876 0.3301 0.6943 0.086 Uiso 0.587(5) 1 calc R U P A 1
H11B H 0.2780 0.6354 0.6815 0.086 Uiso 0.587(5) 1 calc R U P A 1
C12 C 0.2389(3) 0.4236(8) 0.58882(19) 0.0602(11) Uani 0.587(5) 1 d D . P A 1
H12A H 0.3094 0.4409 0.5695 0.072 Uiso 0.587(5) 1 calc R U P A 1
H12B H 0.2134 0.2466 0.5780 0.072 Uiso 0.587(5) 1 calc R U P A 1
C9A C 0.2758(3) 0.6015(11) 0.6176(3) 0.0605(16) Uani 0.413(5) 1 d D . P A 2
H9AA H 0.2951 0.7225 0.6575 0.073 Uiso 0.413(5) 1 calc R U P A 2
H9AB H 0.3383 0.5709 0.5888 0.073 Uiso 0.413(5) 1 calc R U P A 2
C10A C 0.2387(7) 0.3471(16) 0.6491(5) 0.078(2) Uani 0.413(5) 1 d D . P A 2
H10A H 0.2282 0.2196 0.6093 0.093 Uiso 0.413(5) 1 calc R U P A 2
H10B H 0.2930 0.2786 0.6835 0.093 Uiso 0.413(5) 1 calc R U P A 2
C11A C 0.0619(4) 0.4861(18) 0.6394(4) 0.092(2) Uani 0.413(5) 1 d D . P A 2
H11C H -0.0026 0.5083 0.6666 0.110 Uiso 0.413(5) 1 calc R U P A 2
H11D H 0.0466 0.3613 0.5997 0.110 Uiso 0.413(5) 1 calc R U P A 2
C12A C 0.0903(5) 0.7432(15) 0.6064(5) 0.0715(19) Uani 0.413(5) 1 d D . P A 2
H12C H 0.0352 0.7974 0.5705 0.086 Uiso 0.413(5) 1 calc R U P A 2
H12D H 0.0963 0.8768 0.6448 0.086 Uiso 0.413(5) 1 calc R U P A 2
N1 N 0.1681(3) 0.6147(8) 0.5533(2) 0.0498(9) Uani 0.587(5) 1 d D . P A 1
N1A N 0.1912(4) 0.7173(12) 0.5700(3) 0.0500(13) Uani 0.413(5) 1 d D . P A 2
O1 O 0.50838(9) 0.7271(3) 0.39490(8) 0.0778(5) Uani 1 1 d . . . . .
H1 H 0.4901 0.8236 0.4286 0.117 Uiso 1 1 calc R U . . .
O2 O 0.37641(9) 0.9120(3) 0.49358(7) 0.0713(4) Uani 1 1 d . . . . .
O3 O 0.13086(9) 0.9033(3) 0.46146(7) 0.0706(4) Uani 1 1 d . . . . .
O4 O 0.1428(10) 0.4649(18) 0.7018(4) 0.0787(19) Uani 0.587(5) 1 d D . P A 1
O4A O 0.1404(14) 0.380(2) 0.6871(6) 0.087(3) Uani 0.413(5) 1 d D . P A 2


_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 1.363(2) . ?
C1 C6 1.398(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 O1 1.349(2) . ?
C5 C6 1.410(2) . ?
C6 C7 1.452(2) . ?
C7 O2 1.2305(19) . ?
C7 C8 1.534(2) . ?
C8 O3 1.2193(19) . ?
C8 N1A 1.346(6) . ?
C8 N1 1.353(4) . ?
C9 N1 1.477(6) . ?
C9 C10 1.511(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O4 1.432(12) . ?
C10 H10 0.9300 . ?
C11 O4 1.411(13) . ?
C11 C12 1.496(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N1 1.448(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9A N1A 1.465(7) . ?
C9A C10A 1.491(10) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C10A O4A 1.449(17) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11A O4A 1.394(17) . ?
C11A C12A 1.482(10) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C12A N1A 1.458(8) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
O1 H1 0.8200 . ?

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 121.47(17) . . ?
C2 C1 H1A 119.3 . . ?
C6 C1 H1A 119.3 . . ?
C1 C2 C3 118.99(18) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 121.49(18) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.18(17) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
O1 C5 C4 118.11(15) . . ?
O1 C5 C6 122.51(15) . . ?
C4 C5 C6 119.38(16) . . ?
C1 C6 C5 118.48(15) . . ?
C1 C6 C7 120.64(14) . . ?
C5 C6 C7 120.86(14) . . ?
O2 C7 C6 123.76(14) . . ?
O2 C7 C8 117.87(15) . . ?
C6 C7 C8 118.26(14) . . ?
O3 C8 N1A 125.1(3) . . ?
O3 C8 N1 121.6(2) . . ?
O3 C8 C7 117.53(15) . . ?
N1A C8 C7 113.9(3) . . ?
N1 C8 C7 119.9(2) . . ?
N1 C9 C10 108.7(3) . . ?
N1 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
N1 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.3 . . ?
O4 C10 C9 111.3(4) . . ?
O4 C10 H10 124.3 . . ?
C9 C10 H10 124.3 . . ?
O4 C11 C12 112.6(6) . . ?
O4 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
O4 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 C11 110.0(3) . . ?
N1 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
N1 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N1A C9A C10A 109.8(5) . . ?
N1A C9A H9AA 109.7 . . ?
C10A C9A H9AA 109.7 . . ?
N1A C9A H9AB 109.7 . . ?
C10A C9A H9AB 109.7 . . ?
H9AA C9A H9AB 108.2 . . ?
O4A C10A C9A 111.5(7) . . ?
O4A C10A H10A 109.3 . . ?
C9A C10A H10A 109.3 . . ?
O4A C10A H10B 109.3 . . ?
C9A C10A H10B 109.3 . . ?
H10A C10A H10B 108.0 . . ?
O4A C11A C12A 114.3(8) . . ?
O4A C11A H11C 108.7 . . ?
C12A C11A H11C 108.7 . . ?
O4A C11A H11D 108.7 . . ?
C12A C11A H11D 108.7 . . ?
H11C C11A H11D 107.6 . . ?
N1A C12A C11A 109.2(6) . . ?
N1A C12A H12C 109.8 . . ?
C11A C12A H12C 109.8 . . ?
N1A C12A H12D 109.8 . . ?
C11A C12A H12D 109.8 . . ?
H12C C12A H12D 108.3 . . ?
C8 N1 C12 123.7(3) . . ?
C8 N1 C9 122.5(4) . . ?
C12 N1 C9 113.7(4) . . ?
C8 N1A C12A 119.6(5) . . ?
C8 N1A C9A 126.5(5) . . ?
C12A N1A C9A 113.5(5) . . ?
C5 O1 H1 109.5 . . ?
C11 O4 C10 110.2(6) . . ?
C11A O4A C10A 110.5(8) . . ?

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 -0.2(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 O1 179.38(17) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C2 C1 C6 C7 -178.70(16) . . . . ?
O1 C5 C6 C1 -179.27(15) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
O1 C5 C6 C7 -0.7(3) . . . . ?
C4 C5 C6 C7 178.95(16) . . . . ?
C1 C6 C7 O2 176.90(16) . . . . ?
C5 C6 C7 O2 -1.6(3) . . . . ?
C1 C6 C7 C8 -7.0(2) . . . . ?
C5 C6 C7 C8 174.48(15) . . . . ?
O2 C7 C8 O3 96.4(2) . . . . ?
C6 C7 C8 O3 -79.9(2) . . . . ?
O2 C7 C8 N1A -63.6(3) . . . . ?
C6 C7 C8 N1A 120.1(3) . . . . ?
O2 C7 C8 N1 -94.8(3) . . . . ?
C6 C7 C8 N1 88.9(3) . . . . ?
N1 C9 C10 O4 -55.8(7) . . . . ?
O4 C11 C12 N1 54.7(7) . . . . ?
N1A C9A C10A O4A -54.5(10) . . . . ?
O4A C11A C12A N1A 54.3(11) . . . . ?
O3 C8 N1 C12 168.6(3) . . . . ?
C7 C8 N1 C12 0.3(4) . . . . ?
O3 C8 N1 C9 -14.0(4) . . . . ?
C7 C8 N1 C9 177.7(3) . . . . ?
C11 C12 N1 C8 125.8(5) . . . . ?
C11 C12 N1 C9 -51.7(5) . . . . ?
C10 C9 N1 C8 -125.1(5) . . . . ?
C10 C9 N1 C12 52.5(5) . . . . ?
O3 C8 N1A C12A 17.6(6) . . . . ?
C7 C8 N1A C12A 175.8(4) . . . . ?
O3 C8 N1A C9A -169.4(4) . . . . ?
C7 C8 N1A C9A -11.1(6) . . . . ?
C11A C12A N1A C8 122.4(8) . . . . ?
C11A C12A N1A C9A -51.6(8) . . . . ?
C10A C9A N1A C8 -120.5(7) . . . . ?
C10A C9A N1A C12A 53.0(7) . . . . ?
C12 C11 O4 C10 -59.4(8) . . . . ?
C9 C10 O4 C11 60.1(7) . . . . ?
C12A C11A O4A C10A -57.6(12) . . . . ?
C9A C10A O4A C11A 57.1(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9A H9AB O1 0.97 2.46 3.202(4) 133.0 3_666
C9A H9AB O2 0.97 2.50 3.049(5) 116.0 .
C12A H12C O3 0.97 2.63 3.493(7) 148.5 3_576
C12 H12A O1 0.97 2.51 3.274(3) 135.9 3_666
C9 H9B O3 0.97 2.56 3.485(5) 160.2 3_576
O1 H1 O2 0.82 2.53 3.0450(19) 121.8 3_676
O1 H1 O2 0.82 1.94 2.6515(17) 145.3 .

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.028

