# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_cxy3457_0m
_database_code_depnum_ccdc_archive 'CCDC 2159810'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2022-03-17 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_audit_creation_date             2021-12-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 N2 O6'
_chemical_formula_sum            'C18 H16 N2 O6'
_chemical_formula_weight         356.33
_chemical_absolute_configuration ad
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.6781(3)
_cell_length_b                   9.7730(6)
_cell_length_c                   15.2351(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.831(3)
_cell_angle_gamma                90
_cell_volume                     844.40(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.780
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1371 before and 0.0660 after correction.
The Ratio of minimum to maximum transmission is 0.7221.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14263
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.265
_diffrn_reflns_theta_min         2.904
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3003
_reflns_number_total             3048
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1367 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.0121(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.079
_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)+(0.0445P)²+0.0858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0747
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C11(H11), C18(H18), C4(H4), C2(H2), C14(H14), C15(H15),
 C16(H16)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
;
_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
O5 O 0.9503(2) 0.52586(14) 0.31196(8) 0.0190(3) Uani 1 1 d . . . . .
O1 O 1.2545(3) 0.42862(19) 0.70675(10) 0.0417(5) Uani 1 1 d . . . . .
O3 O 0.3794(2) 0.78316(16) 0.46851(9) 0.0277(4) Uani 1 1 d . . . . .
O4 O 0.3294(2) 0.74073(14) 0.60620(8) 0.0221(3) Uani 1 1 d . . . . .
O2 O 0.9766(3) 0.52808(16) 0.77475(9) 0.0327(4) Uani 1 1 d . . . . .
O6 O 1.2546(2) 0.42446(14) 0.38723(9) 0.0223(3) Uani 1 1 d . . . . .
N1 N 1.0693(3) 0.49072(18) 0.70771(11) 0.0237(4) Uani 1 1 d . . . . .
N2 N 0.4368(2) 0.72809(17) 0.53873(10) 0.0185(4) Uani 1 1 d . . . . .
C13 C 0.1475(4) 0.2995(2) -0.03013(14) 0.0315(5) Uani 1 1 d . . . . .
H13 H 0.022791 0.287257 -0.073319 0.038 Uiso 1 1 calc R U . . .
C12 C 0.1628(4) 0.2170(2) 0.04407(14) 0.0303(5) Uani 1 1 d . . . . .
H12 H 0.049206 0.147128 0.051618 0.036 Uiso 1 1 calc R U . . .
C11 C 0.3449(3) 0.2367(2) 0.10750(13) 0.0246(4) Uani 1 1 d . . . . .
H11 H 0.354562 0.179176 0.157799 0.030 Uiso 1 1 calc R U . . .
C10 C 0.5131(3) 0.3390(2) 0.09880(13) 0.0214(4) Uani 1 1 d . . . . .
C9 C 0.7017(3) 0.3608(2) 0.17147(13) 0.0224(4) Uani 1 1 d . . . . .
H9A H 0.800806 0.277518 0.176401 0.027 Uiso 1 1 calc R U . . .
H9B H 0.623794 0.371915 0.227754 0.027 Uiso 1 1 calc R U . . .
C8 C 0.8613(3) 0.4838(2) 0.15862(12) 0.0194(4) Uani 1 1 d . . . . .
H8A H 0.930694 0.476407 0.100457 0.023 Uiso 1 1 calc R U . . .
H8B H 0.764604 0.568057 0.158507 0.023 Uiso 1 1 calc R U . . .
C7 C 1.0593(3) 0.4968(2) 0.22879(12) 0.0185(4) Uani 1 1 d . . . . .
H7 H 1.146044 0.407879 0.233969 0.022 Uiso 1 1 calc R U . . .
C6 C 1.0697(3) 0.48555(19) 0.38492(12) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.9496(3) 0.5270(2) 0.46619(12) 0.0167(4) Uani 1 1 d . . . . .
C18 C 1.0541(3) 0.48686(18) 0.54634(12) 0.0164(4) Uani 1 1 d . . . . .
H18 H 1.194248 0.433583 0.548854 0.020 Uiso 1 1 calc R U . . .
C1 C 0.9494(3) 0.5262(2) 0.62263(12) 0.0185(4) Uani 1 1 d . . . . .
C3 C 0.6488(3) 0.64125(19) 0.54134(12) 0.0168(4) Uani 1 1 d . . . . .
C4 C 0.7445(3) 0.60565(19) 0.46278(12) 0.0166(4) Uani 1 1 d . . . . .
H4 H 0.672545 0.633913 0.408139 0.020 Uiso 1 1 calc R U . . .
C2 C 0.7450(3) 0.60267(19) 0.62281(12) 0.0175(4) Uani 1 1 d . . . . .
H2 H 0.674472 0.627360 0.675810 0.021 Uiso 1 1 calc R U . . .
C14 C 0.3156(4) 0.3996(2) -0.04048(14) 0.0315(5) Uani 1 1 d . . . . .
H14 H 0.307857 0.455221 -0.091673 0.038 Uiso 1 1 calc R U . . .
C15 C 0.4961(4) 0.4197(2) 0.02327(14) 0.0274(4) Uani 1 1 d . . . . .
H15 H 0.609462 0.489504 0.015248 0.033 Uiso 1 1 calc R U . . .
C16 C 1.2294(3) 0.6083(2) 0.20800(12) 0.0225(4) Uani 1 1 d . . . . .
H16 H 1.307639 0.599053 0.154621 0.027 Uiso 1 1 calc R U . . .
C17 C 1.2822(4) 0.7173(2) 0.25546(14) 0.0300(5) Uani 1 1 d . . . . .
H17A H 1.209300 0.731805 0.309480 0.036 Uiso 1 1 calc R U . . .
H17B H 1.393357 0.781686 0.235753 0.036 Uiso 1 1 calc R U . . .


_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
O5 C7 1.465(2) . ?
O5 C6 1.333(2) . ?
O1 N1 1.215(2) . ?
O3 N2 1.227(2) . ?
O4 N2 1.227(2) . ?
O2 N1 1.228(2) . ?
O6 C6 1.207(2) . ?
N1 C1 1.475(2) . ?
N2 C3 1.472(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.388(3) . ?
C13 C14 1.381(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.393(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.393(3) . ?
C10 C9 1.517(3) . ?
C10 C15 1.395(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.524(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.518(2) . ?
C7 H7 1.0000 . ?
C7 C16 1.501(3) . ?
C6 C5 1.499(2) . ?
C5 C18 1.388(3) . ?
C5 C4 1.394(3) . ?
C18 H18 0.9500 . ?
C18 C1 1.386(3) . ?
C1 C2 1.381(3) . ?
C3 C4 1.383(3) . ?
C3 C2 1.384(3) . ?
C4 H4 0.9500 . ?
C2 H2 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.391(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.314(3) . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?

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 O5 C7 116.40(13) . . ?
O1 N1 O2 124.45(16) . . ?
O1 N1 C1 117.97(16) . . ?
O2 N1 C1 117.56(16) . . ?
O3 N2 C3 117.27(14) . . ?
O4 N2 O3 124.36(15) . . ?
O4 N2 C3 118.37(14) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C14 C13 C12 119.25(19) . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 119.93(19) . . ?
C11 C12 H12 120.0 . . ?
C12 C11 H11 119.3 . . ?
C10 C11 C12 121.47(19) . . ?
C10 C11 H11 119.3 . . ?
C11 C10 C9 119.58(17) . . ?
C11 C10 C15 117.66(18) . . ?
C15 C10 C9 122.74(18) . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C10 C9 C8 114.82(15) . . ?
H9A C9 H9B 107.5 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C7 C8 C9 113.58(15) . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
O5 C7 C8 107.20(13) . . ?
O5 C7 H7 109.1 . . ?
O5 C7 C16 110.21(15) . . ?
C8 C7 H7 109.1 . . ?
C16 C7 C8 111.98(15) . . ?
C16 C7 H7 109.1 . . ?
O5 C6 C5 112.06(14) . . ?
O6 C6 O5 125.22(17) . . ?
O6 C6 C5 122.71(16) . . ?
C18 C5 C6 117.28(15) . . ?
C18 C5 C4 120.59(16) . . ?
C4 C5 C6 122.12(15) . . ?
C5 C18 H18 120.8 . . ?
C1 C18 C5 118.49(16) . . ?
C1 C18 H18 120.8 . . ?
C18 C1 N1 118.23(17) . . ?
C2 C1 N1 118.49(16) . . ?
C2 C1 C18 123.19(17) . . ?
C4 C3 N2 118.51(15) . . ?
C4 C3 C2 123.59(16) . . ?
C2 C3 N2 117.87(16) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 C5 118.00(16) . . ?
C3 C4 H4 121.0 . . ?
C1 C2 C3 116.13(17) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C7 C16 H16 116.4 . . ?
C17 C16 C7 127.21(19) . . ?
C17 C16 H16 116.4 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?

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
O5 C7 C16 C17 0.8(3) . . . . ?
O5 C6 C5 C18 178.03(15) . . . . ?
O5 C6 C5 C4 -3.5(2) . . . . ?
O1 N1 C1 C18 0.0(3) . . . . ?
O1 N1 C1 C2 -176.82(18) . . . . ?
O3 N2 C3 C4 -12.0(2) . . . . ?
O3 N2 C3 C2 166.33(16) . . . . ?
O4 N2 C3 C4 167.94(15) . . . . ?
O4 N2 C3 C2 -13.7(2) . . . . ?
O2 N1 C1 C18 178.87(17) . . . . ?
O2 N1 C1 C2 2.0(3) . . . . ?
O6 C6 C5 C18 -2.9(3) . . . . ?
O6 C6 C5 C4 175.53(18) . . . . ?
N1 C1 C2 C3 175.61(16) . . . . ?
N2 C3 C4 C5 177.97(16) . . . . ?
N2 C3 C2 C1 -177.30(16) . . . . ?
C13 C12 C11 C10 0.6(3) . . . . ?
C13 C14 C15 C10 0.5(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C12 C11 C10 C9 177.26(17) . . . . ?
C12 C11 C10 C15 -1.3(3) . . . . ?
C11 C10 C9 C8 -174.51(17) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C10 C9 C8 C7 -175.70(15) . . . . ?
C9 C10 C15 C14 -177.73(19) . . . . ?
C9 C8 C7 O5 -66.0(2) . . . . ?
C9 C8 C7 C16 172.98(15) . . . . ?
C8 C7 C16 C17 120.1(2) . . . . ?
C7 O5 C6 O6 -2.2(3) . . . . ?
C7 O5 C6 C5 176.82(14) . . . . ?
C6 O5 C7 C8 152.63(15) . . . . ?
C6 O5 C7 C16 -85.27(19) . . . . ?
C6 C5 C18 C1 178.71(15) . . . . ?
C6 C5 C4 C3 -178.74(16) . . . . ?
C5 C18 C1 N1 -176.18(17) . . . . ?
C5 C18 C1 C2 0.5(3) . . . . ?
C18 C5 C4 C3 -0.3(3) . . . . ?
C18 C1 C2 C3 -1.1(3) . . . . ?
C4 C5 C18 C1 0.2(3) . . . . ?
C4 C3 C2 C1 0.9(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C14 C13 C12 C11 0.7(3) . . . . ?
C15 C10 C9 C8 3.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
