# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shx97
_database_code_depnum_ccdc_archive 'CCDC 2120314'
loop_
_audit_author_name
_audit_author_address
'Yunyun Liu'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2021-11-05 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N2 O5, H2 O'
_chemical_formula_sum            'C20 H22 N O6'
_chemical_formula_weight         372.38

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      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                   8.1557(16)
_cell_length_b                   8.4598(17)
_cell_length_c                   16.325(3)
_cell_angle_alpha                79.95(3)
_cell_angle_beta                 84.74(3)
_cell_angle_gamma                63.26(3)
_cell_volume                     990.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    6212
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             394
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7723
_diffrn_reflns_av_unetI/netI     0.2590
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.995
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3434
_reflns_number_gt                2259
_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       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0845P)²+0.1041P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3434
_refine_ls_number_parameters     253
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1800
_refine_ls_wR_factor_gt          0.1545
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.161
_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
N1 N 0.9320(2) 0.3105(2) 0.01216(12) 0.0409(5) Uani 1 1 d . . . . .
H1A H 0.974829 0.303811 -0.037920 0.049 Uiso 1 1 calc R U . . .
O1 O 0.9983(3) -0.0238(2) 0.24479(12) 0.0674(6) Uani 1 1 d . . . . .
O2 O 0.5446(3) 0.6970(2) 0.15622(13) 0.0781(7) Uani 1 1 d . . . . .
O3 O 0.5334(2) 0.4480(2) 0.22416(11) 0.0606(5) Uani 1 1 d . . . . .
O4 O 0.4217(3) 0.9134(2) -0.12558(12) 0.0664(6) Uani 1 1 d . . . . .
O5 O 0.6278(2) 0.8325(2) -0.22922(10) 0.0581(5) Uani 1 1 d . . . . .
O6 O 1.0846(3) 0.2444(3) -0.15050(12) 0.0643(6) Uani 1 1 d D . . . .
H6B H 1.063(4) 0.173(4) -0.175(2) 0.096 Uiso 1 1 d D U . . .
H6A H 1.199(3) 0.183(4) -0.140(2) 0.096 Uiso 1 1 d D U . . .
C1 C 0.9242(3) 0.3979(4) 0.29483(16) 0.0546(7) Uani 1 1 d . . . . .
H1B H 0.944557 0.450274 0.242373 0.066 Uiso 1 1 calc R U . . .
C2 C 0.9060(4) 0.4815(5) 0.3636(2) 0.0754(9) Uani 1 1 d . . . . .
H2A H 0.914854 0.588801 0.357140 0.091 Uiso 1 1 calc R U . . .
C3 C 0.8748(6) 0.4050(6) 0.4409(2) 0.0925(11) Uani 1 1 d . . . . .
H3A H 0.861418 0.461087 0.486951 0.111 Uiso 1 1 calc R U . . .
C4 C 0.8633(6) 0.2444(6) 0.4505(2) 0.0915(11) Uani 1 1 d . . . . .
H4A H 0.843086 0.192949 0.503215 0.110 Uiso 1 1 calc R U . . .
C5 C 0.8816(4) 0.1594(4) 0.38261(17) 0.0682(8) Uani 1 1 d . . . . .
H5A H 0.873438 0.051737 0.389464 0.082 Uiso 1 1 calc R U . . .
C6 C 0.9125(3) 0.2376(3) 0.30364(15) 0.0491(6) Uani 1 1 d . . . . .
C7 C 0.9388(3) 0.1407(3) 0.23197(15) 0.0479(6) Uani 1 1 d . . . . .
C8 C 0.8995(3) 0.2397(3) 0.14769(14) 0.0417(6) Uani 1 1 d . . . . .
C9 C 0.7586(3) 0.4158(3) 0.12055(14) 0.0406(6) Uani 1 1 d . . . . .
C10 C 0.7805(3) 0.4550(3) 0.03587(14) 0.0410(6) Uani 1 1 d . . . . .
C11 C 1.0052(3) 0.1804(3) 0.07768(14) 0.0410(6) Uani 1 1 d . . . . .
C12 C 1.1756(3) 0.0141(3) 0.06798(16) 0.0512(7) Uani 1 1 d . . . . .
H12A H 1.144301 -0.071984 0.051090 0.077 Uiso 1 1 calc R U . . .
H12B H 1.238202 -0.034413 0.120070 0.077 Uiso 1 1 calc R U . . .
H12C H 1.254158 0.041424 0.026522 0.077 Uiso 1 1 calc R U . . .
C13 C 0.6044(3) 0.5355(3) 0.16790(15) 0.0509(6) Uani 1 1 d . . . . .
C14 C 0.3686(5) 0.5570(6) 0.2691(2) 0.1037(14) Uani 1 1 d D . . . .
H14A H 0.255085 0.625686 0.244013 0.124 Uiso 1 1 calc R U . . .
C15 C 0.3957(8) 0.5492(9) 0.3490(3) 0.176(3) Uani 1 1 d D . . . .
H15A H 0.443304 0.427077 0.375735 0.265 Uiso 1 1 calc R U . . .
H15B H 0.281322 0.619584 0.375058 0.265 Uiso 1 1 calc R U . . .
H15C H 0.481948 0.595291 0.353873 0.265 Uiso 1 1 calc R U . . .
C16 C 0.6672(3) 0.6103(3) -0.02121(15) 0.0444(6) Uani 1 1 d . . . . .
H16A H 0.561072 0.694374 0.000989 0.053 Uiso 1 1 calc R U . . .
C17 C 0.6981(3) 0.6455(3) -0.10144(15) 0.0470(6) Uani 1 1 d . . . . .
H17A H 0.802981 0.566324 -0.126590 0.056 Uiso 1 1 calc R U . . .
C18 C 0.5672(3) 0.8094(3) -0.15110(15) 0.0472(6) Uani 1 1 d . . . . .
C19 C 0.5021(4) 0.9859(4) -0.28452(18) 0.0756(9) Uani 1 1 d . . . . .
H19A H 0.385900 0.980633 -0.285614 0.091 Uiso 1 1 calc R U . . .
H19B H 0.479172 1.095790 -0.264784 0.091 Uiso 1 1 calc R U . . .
C20 C 0.5835(6) 0.9832(6) -0.3676(2) 0.1174(17) Uani 1 1 d . . . . .
H20A H 0.693595 0.997495 -0.366829 0.176 Uiso 1 1 calc R U . . .
H20B H 0.498017 1.079302 -0.405377 0.176 Uiso 1 1 calc R U . . .
H20C H 0.612602 0.871033 -0.385337 0.176 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
N1 C11 1.352(3) . ?
N1 C10 1.374(3) . ?
N1 H1A 0.8600 . ?
O1 C7 1.234(3) . ?
O2 C13 1.211(3) . ?
O3 C13 1.333(3) . ?
O3 C14 1.461(3) . ?
O4 C18 1.205(3) . ?
O5 C18 1.339(3) . ?
O5 C19 1.453(3) . ?
O6 H6B 0.868(17) . ?
O6 H6A 0.853(17) . ?
C1 C6 1.384(4) . ?
C1 C2 1.390(4) . ?
C1 H1B 0.9300 . ?
C2 C3 1.372(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.384(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.398(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.489(4) . ?
C7 C8 1.461(3) . ?
C8 C11 1.390(3) . ?
C8 C9 1.435(3) . ?
C9 C10 1.379(3) . ?
C9 C13 1.467(3) . ?
C10 C16 1.444(3) . ?
C11 C12 1.488(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.328(6) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.319(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.468(3) . ?
C17 H17A 0.9300 . ?
C19 C20 1.453(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C11 N1 C10 111.30(18) . . ?
C11 N1 H1A 124.3 . . ?
C10 N1 H1A 124.3 . . ?
C13 O3 C14 116.8(2) . . ?
C18 O5 C19 116.1(2) . . ?
H6B O6 H6A 102(2) . . ?
C6 C1 C2 120.7(3) . . ?
C6 C1 H1B 119.6 . . ?
C2 C1 H1B 119.6 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 C7 122.2(2) . . ?
C5 C6 C7 118.3(3) . . ?
O1 C7 C8 121.0(2) . . ?
O1 C7 C6 119.0(2) . . ?
C8 C7 C6 119.9(2) . . ?
C11 C8 C9 106.5(2) . . ?
C11 C8 C7 124.5(2) . . ?
C9 C8 C7 128.8(2) . . ?
C10 C9 C8 107.74(19) . . ?
C10 C9 C13 122.7(2) . . ?
C8 C9 C13 129.4(2) . . ?
N1 C10 C9 106.75(19) . . ?
N1 C10 C16 124.0(2) . . ?
C9 C10 C16 129.2(2) . . ?
N1 C11 C8 107.64(19) . . ?
N1 C11 C12 121.1(2) . . ?
C8 C11 C12 131.2(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 O3 123.2(2) . . ?
O2 C13 C9 123.9(2) . . ?
O3 C13 C9 112.9(2) . . ?
C15 C14 O3 113.9(4) . . ?
C15 C14 H14A 123.0 . . ?
O3 C14 H14A 123.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C10 126.9(2) . . ?
C17 C16 H16A 116.5 . . ?
C10 C16 H16A 116.5 . . ?
C16 C17 C18 120.1(2) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
O4 C18 O5 123.0(2) . . ?
O4 C18 C17 124.8(2) . . ?
O5 C18 C17 112.2(2) . . ?
C20 C19 O5 108.8(3) . . ?
C20 C19 H19A 109.9 . . ?
O5 C19 H19A 109.9 . . ?
C20 C19 H19B 109.9 . . ?
O5 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C6 C1 C2 C3 -0.4(5) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C1 C6 C7 -177.5(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 C7 177.7(3) . . . . ?
C1 C6 C7 O1 151.6(3) . . . . ?
C5 C6 C7 O1 -26.0(4) . . . . ?
C1 C6 C7 C8 -26.5(3) . . . . ?
C5 C6 C7 C8 155.8(2) . . . . ?
O1 C7 C8 C11 -38.0(4) . . . . ?
C6 C7 C8 C11 140.1(2) . . . . ?
O1 C7 C8 C9 146.5(3) . . . . ?
C6 C7 C8 C9 -35.4(4) . . . . ?
C11 C8 C9 C10 1.4(3) . . . . ?
C7 C8 C9 C10 177.5(2) . . . . ?
C11 C8 C9 C13 176.3(2) . . . . ?
C7 C8 C9 C13 -7.6(4) . . . . ?
C11 N1 C10 C9 1.1(3) . . . . ?
C11 N1 C10 C16 -176.3(2) . . . . ?
C8 C9 C10 N1 -1.5(3) . . . . ?
C13 C9 C10 N1 -176.8(2) . . . . ?
C8 C9 C10 C16 175.7(2) . . . . ?
C13 C9 C10 C16 0.4(4) . . . . ?
C10 N1 C11 C8 -0.2(3) . . . . ?
C10 N1 C11 C12 -177.1(2) . . . . ?
C9 C8 C11 N1 -0.8(3) . . . . ?
C7 C8 C11 N1 -177.1(2) . . . . ?
C9 C8 C11 C12 175.8(3) . . . . ?
C7 C8 C11 C12 -0.5(4) . . . . ?
C14 O3 C13 O2 4.0(4) . . . . ?
C14 O3 C13 C9 -174.6(3) . . . . ?
C10 C9 C13 O2 -40.5(4) . . . . ?
C8 C9 C13 O2 145.3(3) . . . . ?
C10 C9 C13 O3 138.0(2) . . . . ?
C8 C9 C13 O3 -36.2(4) . . . . ?
C13 O3 C14 C15 -110.7(5) . . . . ?
N1 C10 C16 C17 -6.4(4) . . . . ?
C9 C10 C16 C17 176.9(3) . . . . ?
C10 C16 C17 C18 179.3(2) . . . . ?
C19 O5 C18 O4 -4.0(4) . . . . ?
C19 O5 C18 C17 176.3(2) . . . . ?
C16 C17 C18 O4 -5.5(4) . . . . ?
C16 C17 C18 O5 174.2(2) . . . . ?
C18 O5 C19 C20 -175.8(3) . . . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.049

