# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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data_cu_jy_05_148_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2023034'
loop_
_audit_author_name
_audit_author_address
'Jinghui Yang'
;Stanford University
United States of America
;
_audit_update_record             
;
2020-08-12 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;
_audit_creation_date             2020-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 N2 O9'
_chemical_formula_sum            'C22 H20 N2 O9'
_chemical_formula_weight         456.40
_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                   6.8601(4)
_cell_length_b                   20.5081(11)
_cell_length_c                   7.3450(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.7080(10)
_cell_angle_gamma                90
_cell_volume                     1032.20(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9658
_cell_measurement_temperature    100
_cell_measurement_theta_max      80.022
_cell_measurement_theta_min      4.311
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.538
_exptl_absorpt_coefficient_mu    0.983
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1312 before and 0.0429 after correction. 
The Ratio of minimum to maximum transmission is 0.8237. 
The λ/2 correction factor is Not present.'
;

_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            56702
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.238
_diffrn_reflns_theta_min         4.312
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon II'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_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_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4443
_reflns_number_total             4448
_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 (2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT  V8.40A (2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 2128 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       0.0047(7)
_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   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4448
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.019
_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)+(0.0556P)²+0.1350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          
;
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:
 C14(H14), C9(H9), C10(H10), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C19(H19), C3(H3), C18(H18), C4(H4), C21(H21), C22(H22), C5(H5)
;
_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
O8 O 0.97032(17) 0.52214(6) 0.91249(16) 0.0243(2) Uani 1 1 d . . . . .
O5 O 0.99836(18) 0.57803(6) 0.51529(18) 0.0280(3) Uani 1 1 d . . . . .
O6 O 0.74051(17) 0.62285(6) 0.64886(16) 0.0253(3) Uani 1 1 d . . . . .
O7 O 1.24111(18) 0.46735(6) 0.83964(18) 0.0297(3) Uani 1 1 d . . . . .
O9 O 1.26535(18) 0.69136(6) 1.13787(17) 0.0292(3) Uani 1 1 d . . . . .
O3 O 0.12449(18) 0.40185(7) 0.21907(19) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.6243(2) 0.23154(7) 0.45478(19) 0.0366(3) Uani 1 1 d . . . . .
O4 O 0.3734(2) 0.34350(8) 0.1529(3) 0.0474(4) Uani 1 1 d . . . . .
O1 O 0.3821(2) 0.27451(9) 0.5902(2) 0.0466(4) Uani 1 1 d . . . . .
N2 N 0.3009(2) 0.39210(7) 0.2178(2) 0.0265(3) Uani 1 1 d . . . . .
N1 N 0.5542(2) 0.27318(8) 0.5516(2) 0.0299(3) Uani 1 1 d . . . . .
C7 C 0.8252(2) 0.57994(8) 0.5413(2) 0.0212(3) Uani 1 1 d . . . . .
C6 C 0.6813(2) 0.53303(8) 0.4553(2) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.6315(2) 0.43626(8) 0.2716(2) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.680684 0.401539 0.201438 0.027 Uiso 1 1 calc R . . . .
C17 C 0.9266(2) 0.42134(7) 0.7655(2) 0.0217(3) Uani 1 1 d . . . . .
C19 C 0.6049(2) 0.37441(9) 0.7282(2) 0.0242(3) Uani 1 1 d . . . . .
H19 H 0.469777 0.374677 0.751183 0.029 Uiso 1 1 calc R . . . .
C16 C 1.0652(2) 0.47188(8) 0.8415(2) 0.0230(3) Uani 1 1 d . . . . .
C11 C 1.1095(2) 0.76833(8) 0.9418(2) 0.0249(3) Uani 1 1 d . . . . .
H11A H 1.073828 0.774335 0.810740 0.030 Uiso 1 1 calc R . . . .
H11B H 1.134278 0.811608 0.998022 0.030 Uiso 1 1 calc R . . . .
C3 C 0.7551(2) 0.48290(8) 0.3498(2) 0.0222(3) Uani 1 1 d . . . . .
H3 H 0.891185 0.480783 0.331615 0.027 Uiso 1 1 calc R . . . .
C18 C 0.7276(2) 0.42340(8) 0.7963(2) 0.0228(3) Uani 1 1 d . . . . .
H18 H 0.675927 0.458358 0.863897 0.027 Uiso 1 1 calc R . . . .
C14 C 0.9594(2) 0.62507(8) 1.0604(2) 0.0238(3) Uani 1 1 d . . . . .
H14 H 0.867710 0.603155 1.142769 0.029 Uiso 1 1 calc R . . . .
C4 C 0.3551(2) 0.49161(8) 0.3998(2) 0.0249(3) Uani 1 1 d . . . . .
H4 H 0.218486 0.494194 0.414719 0.030 Uiso 1 1 calc R . . . .
C21 C 0.8804(2) 0.32282(8) 0.5891(2) 0.0229(3) Uani 1 1 d . . . . .
H21 H 0.930268 0.288969 0.516248 0.027 Uiso 1 1 calc R . . . .
C9 C 0.8436(2) 0.67460(8) 0.9345(2) 0.0234(3) Uani 1 1 d . . . . .
H9 H 0.702453 0.673977 0.962999 0.028 Uiso 1 1 calc R . . . .
C20 C 0.6844(2) 0.32506(8) 0.6259(2) 0.0236(3) Uani 1 1 d . . . . .
C22 C 1.0020(3) 0.37123(8) 0.6613(2) 0.0232(3) Uani 1 1 d . . . . .
H22 H 1.137468 0.370278 0.639788 0.028 Uiso 1 1 calc R . . . .
C12 C 1.2876(3) 0.72464(8) 0.9677(2) 0.0276(3) Uani 1 1 d . . . . .
H12A H 1.293079 0.692977 0.866360 0.033 Uiso 1 1 calc R . . . .
H12B H 1.408729 0.750924 0.972381 0.033 Uiso 1 1 calc R . . . .
C1 C 0.4333(2) 0.44191(8) 0.2989(2) 0.0224(3) Uani 1 1 d . . . . .
C5 C 0.4819(2) 0.53789(8) 0.4792(2) 0.0239(3) Uani 1 1 d . . . . .
H5 H 0.432238 0.572561 0.549155 0.029 Uiso 1 1 calc R . . . .
C10 C 0.9486(2) 0.73239(8) 1.0372(2) 0.0244(3) Uani 1 1 d . . . . .
H10 H 0.858779 0.761665 1.102689 0.029 Uiso 1 1 calc R . . . .
C13 C 1.0622(2) 0.68311(8) 1.1631(2) 0.0250(3) Uani 1 1 d . . . . .
H13 H 1.027811 0.686364 1.293625 0.030 Uiso 1 1 calc R . . . .
C15 C 1.0937(2) 0.57500(8) 0.9839(2) 0.0257(3) Uani 1 1 d . . . . .
H15A H 1.168933 0.594301 0.885546 0.031 Uiso 1 1 calc R . . . .
H15B H 1.186596 0.558602 1.080554 0.031 Uiso 1 1 calc R . . . .
C8 C 0.8628(2) 0.67438(8) 0.7305(2) 0.0250(3) Uani 1 1 d . . . . .
H8A H 0.821868 0.717156 0.679202 0.030 Uiso 1 1 calc R . . . .
H8B H 1.000668 0.666951 0.702102 0.030 Uiso 1 1 calc R . . . .


_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
O8 C16 1.338(2) . ?
O8 C15 1.4578(19) . ?
O5 C7 1.213(2) . ?
O6 C7 1.334(2) . ?
O6 C8 1.4602(19) . ?
O7 C16 1.211(2) . ?
O9 C12 1.438(2) . ?
O9 C13 1.425(2) . ?
O3 N2 1.2268(19) . ?
O2 N1 1.224(2) . ?
O4 N2 1.221(2) . ?
O1 N1 1.228(2) . ?
N2 C1 1.474(2) . ?
N1 C20 1.477(2) . ?
C7 C6 1.497(2) . ?
C6 C3 1.397(2) . ?
C6 C5 1.390(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(2) . ?
C2 C1 1.389(2) . ?
C17 C16 1.497(2) . ?
C17 C18 1.396(2) . ?
C17 C22 1.395(2) . ?
C19 H19 0.9500 . ?
C19 C18 1.388(2) . ?
C19 C20 1.387(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.519(2) . ?
C11 C10 1.525(2) . ?
C3 H3 0.9500 . ?
C18 H18 0.9500 . ?
C14 H14 1.0000 . ?
C14 C9 1.565(2) . ?
C14 C13 1.560(2) . ?
C14 C15 1.506(2) . ?
C4 H4 0.9500 . ?
C4 C1 1.383(2) . ?
C4 C5 1.396(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.385(2) . ?
C21 C22 1.386(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.562(2) . ?
C9 C8 1.511(2) . ?
C22 H22 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C5 H5 0.9500 . ?
C10 H10 1.0000 . ?
C10 C13 1.554(2) . ?
C13 H13 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

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
C16 O8 C15 115.34(13) . . ?
C7 O6 C8 117.56(13) . . ?
C13 O9 C12 108.29(12) . . ?
O3 N2 C1 118.24(14) . . ?
O4 N2 O3 123.78(15) . . ?
O4 N2 C1 117.98(14) . . ?
O2 N1 O1 123.94(16) . . ?
O2 N1 C20 118.04(14) . . ?
O1 N1 C20 118.01(15) . . ?
O5 C7 O6 124.89(15) . . ?
O5 C7 C6 122.98(14) . . ?
O6 C7 C6 112.13(13) . . ?
C3 C6 C7 117.23(14) . . ?
C5 C6 C7 122.27(14) . . ?
C5 C6 C3 120.50(15) . . ?
C3 C2 H2 121.1 . . ?
C3 C2 C1 117.82(15) . . ?
C1 C2 H2 121.1 . . ?
C18 C17 C16 121.85(14) . . ?
C18 C17 C22 120.15(15) . . ?
C22 C17 C16 118.00(14) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C20 C19 C18 118.42(15) . . ?
O8 C16 C17 111.51(14) . . ?
O7 C16 O8 124.54(15) . . ?
O7 C16 C17 123.94(15) . . ?
H11A C11 H11B 108.9 . . ?
C12 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C12 C11 C10 104.62(13) . . ?
C10 C11 H11A 110.8 . . ?
C10 C11 H11B 110.8 . . ?
C6 C3 H3 119.8 . . ?
C2 C3 C6 120.48(14) . . ?
C2 C3 H3 119.8 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.05(15) . . ?
C19 C18 H18 120.0 . . ?
C9 C14 H14 109.4 . . ?
C13 C14 H14 109.4 . . ?
C13 C14 C9 89.75(11) . . ?
C15 C14 H14 109.4 . . ?
C15 C14 C9 121.68(13) . . ?
C15 C14 C13 115.49(14) . . ?
C1 C4 H4 120.8 . . ?
C1 C4 C5 118.33(14) . . ?
C5 C4 H4 120.8 . . ?
C20 C21 H21 120.9 . . ?
C20 C21 C22 118.29(15) . . ?
C22 C21 H21 120.9 . . ?
C14 C9 H9 109.8 . . ?
C10 C9 C14 89.87(12) . . ?
C10 C9 H9 109.8 . . ?
C8 C9 C14 121.22(13) . . ?
C8 C9 H9 109.8 . . ?
C8 C9 C10 114.90(13) . . ?
C19 C20 N1 118.66(14) . . ?
C21 C20 N1 118.65(14) . . ?
C21 C20 C19 122.68(16) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.36(15) . . ?
C21 C22 H22 119.8 . . ?
O9 C12 C11 105.73(14) . . ?
O9 C12 H12A 110.6 . . ?
O9 C12 H12B 110.6 . . ?
C11 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C2 C1 N2 118.19(14) . . ?
C4 C1 N2 118.68(14) . . ?
C4 C1 C2 123.12(15) . . ?
C6 C5 C4 119.73(14) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C11 C10 C9 118.21(13) . . ?
C11 C10 H10 114.0 . . ?
C11 C10 C13 103.56(13) . . ?
C9 C10 H10 114.0 . . ?
C13 C10 C9 90.04(12) . . ?
C13 C10 H10 114.0 . . ?
O9 C13 C14 116.74(13) . . ?
O9 C13 C10 108.12(13) . . ?
O9 C13 H13 113.1 . . ?
C14 C13 H13 113.1 . . ?
C10 C13 C14 90.34(12) . . ?
C10 C13 H13 113.1 . . ?
O8 C15 C14 106.62(13) . . ?
O8 C15 H15A 110.4 . . ?
O8 C15 H15B 110.4 . . ?
C14 C15 H15A 110.4 . . ?
C14 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
O6 C8 C9 109.52(13) . . ?
O6 C8 H8A 109.8 . . ?
O6 C8 H8B 109.8 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?


