# Electronic Supplementary Material (ESI) 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 2283650'
loop_
_audit_author_name
_audit_author_address
'Shuyuan Liang'
;Scigo Instrument Testing Platform
China
;
_audit_update_record             
;
2023-07-22 deposited with the CCDC.	2023-11-29 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            'C16 H14 N2 O5'
_chemical_formula_weight         314.29

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.2559(10)
_cell_length_b                   8.4217(11)
_cell_length_c                   11.5815(15)
_cell_angle_alpha                90.558(7)
_cell_angle_beta                 110.791(7)
_cell_angle_gamma                98.454(7)
_cell_volume                     742.96(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3439
_cell_measurement_theta_min      5.32
_cell_measurement_theta_max      66.78

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.892
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.856
_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      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            7925
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.322
_diffrn_reflns_theta_max         67.136
_diffrn_reflns_theta_full        67.136
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             2548
_reflns_number_gt                2000
_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)+(0.2000P)²] 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         2548
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0766
_refine_ls_wR_factor_ref         0.2378
_refine_ls_wR_factor_gt          0.2154
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.3536(3) 0.1553(3) 0.5435(2) 0.0450(6) Uani 1 1 d . . . . .
H1 H 0.3113 0.0912 0.5947 0.054 Uiso 1 1 calc R U . . .
C2 C 0.5325(3) 0.2034(3) 0.5716(2) 0.0477(6) Uani 1 1 d . . . . .
C3 C 0.6000(3) 0.2974(3) 0.4966(3) 0.0539(7) Uani 1 1 d . . . . .
H3 H 0.7206 0.3264 0.5181 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4865(3) 0.3470(3) 0.3902(2) 0.0523(6) Uani 1 1 d . . . . .
H4 H 0.5294 0.4099 0.3386 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3058(3) 0.3022(3) 0.3599(2) 0.0425(6) Uani 1 1 d . . . . .
C6 C 0.2424(3) 0.2068(2) 0.4368(2) 0.0408(6) Uani 1 1 d . . . . .
C7 C 0.0436(3) 0.1672(2) 0.3855(2) 0.0420(6) Uani 1 1 d . . . . .
H7 H 0.0109 0.0579 0.3461 0.050 Uiso 1 1 calc R U . . .
C8 C -0.0093(3) 0.2875(3) 0.2806(2) 0.0441(6) Uani 1 1 d . . . . .
C9 C 0.1591(3) 0.3397(3) 0.2492(2) 0.0459(6) Uani 1 1 d . . . . .
H9 H 0.1743 0.4548 0.2355 0.055 Uiso 1 1 calc R U . . .
C10 C 0.1251(4) 0.2366(3) 0.1294(2) 0.0584(7) Uani 1 1 d . . . . .
H10 H 0.1568 0.1302 0.1506 0.070 Uiso 1 1 calc R U . . .
C11 C -0.0736(5) 0.2202(4) 0.0609(3) 0.0746(9) Uani 1 1 d . . . . .
H11A H -0.1025 0.3120 0.0121 0.090 Uiso 1 1 calc R U . . .
H11B H -0.1170 0.1231 0.0062 0.090 Uiso 1 1 calc R U . . .
C12 C -0.1520(3) 0.2125(3) 0.1596(3) 0.0587(7) Uani 1 1 d . . . . .
C13 C -0.3136(4) 0.1537(4) 0.1502(4) 0.0864(10) Uani 1 1 d . . . . .
H13A H -0.3955 0.1095 0.0744 0.104 Uiso 1 1 calc R U . . .
H13B H -0.3457 0.1563 0.2194 0.104 Uiso 1 1 calc R U . . .
C14 C -0.0624(3) 0.4252(3) 0.3269(2) 0.0439(5) Uani 1 1 d . . . . .
C15 C 0.2283(5) 0.3143(4) 0.0552(3) 0.0757(10) Uani 1 1 d . . . . .
C16 C 0.3246(8) 0.2765(6) -0.1099(4) 0.125(2) Uani 1 1 d . . . . .
H16A H 0.3245 0.1915 -0.1658 0.188 Uiso 1 1 calc R U . . .
H16B H 0.4435 0.3237 -0.0623 0.188 Uiso 1 1 calc R U . . .
H16C H 0.2632 0.3571 -0.1562 0.188 Uiso 1 1 calc R U . . .
N1 N 0.6552(3) 0.1510(3) 0.6851(2) 0.0608(6) Uani 1 1 d . . . . .
N2 N -0.1045(3) 0.5332(3) 0.3626(2) 0.0548(6) Uani 1 1 d . . . . .
O1 O 0.5969(3) 0.0662(4) 0.7498(3) 0.0926(8) Uani 1 1 d . . . . .
O2 O 0.8123(3) 0.1932(4) 0.7099(3) 0.1005(9) Uani 1 1 d . . . . .
O3 O -0.0371(2) 0.17337(19) 0.47327(17) 0.0503(5) Uani 1 1 d . . . . .
H3A H 0.0158 0.2483 0.5248 0.075 Uiso 1 1 calc R U . . .
O4 O 0.2944(7) 0.4528(4) 0.0691(4) 0.1479(18) Uani 1 1 d . . . . .
O5 O 0.2381(4) 0.2116(3) -0.02717(19) 0.0872(8) 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 C6 1.371(3) . ?
C1 C2 1.389(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(4) . ?
C2 N1 1.465(4) . ?
C3 C4 1.369(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C5 C9 1.493(3) . ?
C6 C7 1.517(3) . ?
C7 O3 1.403(3) . ?
C7 C8 1.572(3) . ?
C7 H7 0.9800 . ?
C8 C14 1.459(3) . ?
C8 C12 1.531(3) . ?
C8 C9 1.562(3) . ?
C9 C10 1.545(3) . ?
C9 H9 0.9800 . ?
C10 C15 1.503(4) . ?
C10 C11 1.532(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.498(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.319(4) . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 N2 1.143(3) . ?
C15 O4 1.197(5) . ?
C15 O5 1.313(4) . ?
C16 O5 1.452(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 O1 1.212(4) . ?
N1 O2 1.220(3) . ?
O3 H3A 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
C6 C1 C2 117.0(2) . . ?
C6 C1 H1 121.5 . . ?
C2 C1 H1 121.5 . . ?
C3 C2 C1 123.0(2) . . ?
C3 C2 N1 118.5(2) . . ?
C1 C2 N1 118.5(2) . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 C9 111.12(18) . . ?
C4 C5 C9 128.8(2) . . ?
C1 C6 C5 121.44(19) . . ?
C1 C6 C7 126.65(19) . . ?
C5 C6 C7 111.9(2) . . ?
O3 C7 C6 115.28(19) . . ?
O3 C7 C8 114.89(16) . . ?
C6 C7 C8 102.73(16) . . ?
O3 C7 H7 107.8 . . ?
C6 C7 H7 107.8 . . ?
C8 C7 H7 107.8 . . ?
C14 C8 C12 110.50(19) . . ?
C14 C8 C9 111.17(17) . . ?
C12 C8 C9 105.93(19) . . ?
C14 C8 C7 109.28(18) . . ?
C12 C8 C7 114.37(18) . . ?
C9 C8 C7 105.46(17) . . ?
C5 C9 C10 114.93(19) . . ?
C5 C9 C8 104.42(18) . . ?
C10 C9 C8 103.91(18) . . ?
C5 C9 H9 111.0 . . ?
C10 C9 H9 111.0 . . ?
C8 C9 H9 111.0 . . ?
C15 C10 C11 112.7(3) . . ?
C15 C10 C9 111.6(2) . . ?
C11 C10 C9 103.96(19) . . ?
C15 C10 H10 109.5 . . ?
C11 C10 H10 109.5 . . ?
C9 C10 H10 109.5 . . ?
C12 C11 C10 105.7(2) . . ?
C12 C11 H11A 110.6 . . ?
C10 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
C10 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C13 C12 C11 128.6(3) . . ?
C13 C12 C8 123.4(3) . . ?
C11 C12 C8 108.0(2) . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
N2 C14 C8 179.7(3) . . ?
O4 C15 O5 123.6(3) . . ?
O4 C15 C10 124.5(3) . . ?
O5 C15 C10 111.9(3) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 N1 O2 122.6(3) . . ?
O1 N1 C2 118.8(2) . . ?
O2 N1 C2 118.6(3) . . ?
C7 O3 H3A 109.5 . . ?
C15 O5 C16 116.5(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
C6 C1 C2 C3 -0.8(3) . . . . ?
C6 C1 C2 N1 179.82(19) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
N1 C2 C3 C4 180.0(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C9 -179.0(2) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 178.57(18) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C9 C5 C6 C1 179.09(18) . . . . ?
C4 C5 C6 C7 -178.11(18) . . . . ?
C9 C5 C6 C7 0.6(2) . . . . ?
C1 C6 C7 O3 42.7(3) . . . . ?
C5 C6 C7 O3 -138.89(19) . . . . ?
C1 C6 C7 C8 168.4(2) . . . . ?
C5 C6 C7 C8 -13.2(2) . . . . ?
O3 C7 C8 C14 26.3(2) . . . . ?
C6 C7 C8 C14 -99.65(19) . . . . ?
O3 C7 C8 C12 -98.1(2) . . . . ?
C6 C7 C8 C12 135.90(19) . . . . ?
O3 C7 C8 C9 145.90(18) . . . . ?
C6 C7 C8 C9 19.9(2) . . . . ?
C6 C5 C9 C10 -100.7(2) . . . . ?
C4 C5 C9 C10 77.9(3) . . . . ?
C6 C5 C9 C8 12.5(2) . . . . ?
C4 C5 C9 C8 -169.0(2) . . . . ?
C14 C8 C9 C5 98.3(2) . . . . ?
C12 C8 C9 C5 -141.60(19) . . . . ?
C7 C8 C9 C5 -20.0(2) . . . . ?
C14 C8 C9 C10 -140.9(2) . . . . ?
C12 C8 C9 C10 -20.8(2) . . . . ?
C7 C8 C9 C10 100.8(2) . . . . ?
C5 C9 C10 C15 -91.0(3) . . . . ?
C8 C9 C10 C15 155.5(2) . . . . ?
C5 C9 C10 C11 147.2(2) . . . . ?
C8 C9 C10 C11 33.8(3) . . . . ?
C15 C10 C11 C12 -155.7(2) . . . . ?
C9 C10 C11 C12 -34.6(3) . . . . ?
C10 C11 C12 C13 -158.5(3) . . . . ?
C10 C11 C12 C8 21.6(3) . . . . ?
C14 C8 C12 C13 -59.7(3) . . . . ?
C9 C8 C12 C13 179.8(3) . . . . ?
C7 C8 C12 C13 64.1(3) . . . . ?
C14 C8 C12 C11 120.2(2) . . . . ?
C9 C8 C12 C11 -0.3(3) . . . . ?
C7 C8 C12 C11 -116.0(2) . . . . ?
C11 C10 C15 O4 99.7(5) . . . . ?
C9 C10 C15 O4 -16.9(5) . . . . ?
C11 C10 C15 O5 -80.4(3) . . . . ?
C9 C10 C15 O5 163.0(3) . . . . ?
C3 C2 N1 O1 -178.5(2) . . . . ?
C1 C2 N1 O1 0.9(4) . . . . ?
C3 C2 N1 O2 0.6(4) . . . . ?
C1 C2 N1 O2 -180.0(2) . . . . ?
O4 C15 O5 C16 -4.2(6) . . . . ?
C10 C15 O5 C16 175.9(3) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.124



