# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_md_lst1
_database_code_depnum_ccdc_archive 'CCDC 1965346'
loop_
_audit_author_name
_audit_author_address
'Jian-Jun Liu'
;Qujing Normal University
China
;
_audit_update_record             
;
2019-11-13 deposited with the CCDC.	2020-01-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H21 N O7'
_chemical_formula_sum            'C20 H21 N O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         387.38

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.3966(5)
_cell_length_b                   5.58400(10)
_cell_length_c                   17.3130(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.5690(10)
_cell_angle_gamma                90
_cell_volume                     1869.20(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9392
_cell_measurement_theta_min      2.2851
_cell_measurement_theta_max      72.3598
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816

_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            20590
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         72.37
_diffrn_reflns_theta_full        72.37
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             3693
_reflns_number_gt                3096
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1122
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_number_reflns         3693
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+1.0054P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.333
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.86174(6) 0.0310(2) 0.46711(7) 0.0202(3) Uani d . . . 1 . .
O O2 0.73058(6) 0.7494(2) 0.12134(6) 0.0175(2) Uani d . . . 1 . .
O O3 0.75012(6) -0.0808(2) 0.42750(8) 0.0301(3) Uani d . . . 1 . .
O O4 0.94204(6) 0.6564(2) 0.32689(7) 0.0234(3) Uani d . . . 1 . .
O O5 0.86521(5) 0.8903(2) 0.23694(7) 0.0200(3) Uani d . . . 1 . .
O O6 0.65977(6) 0.2918(2) 0.35444(7) 0.0206(3) Uani d . . . 1 . .
O O7 0.72059(5) 1.03918(19) 0.20811(7) 0.0176(2) Uani d . . . 1 . .
N N1 0.70118(6) 0.5361(2) 0.27497(8) 0.0139(3) Uani d . . . 1 . .
C C1 0.95526(9) -0.2220(3) 0.54024(11) 0.0252(4) Uani d . . . 1 . .
H H1 0.968067 -0.244924 0.490773 0.038 Uiso calc U . R 1 . .
H H21 0.968186 -0.36441 0.574836 0.038 Uiso calc U . R 1 . .
H H3 0.979576 -0.081944 0.57003 0.038 Uiso calc U . R 1 . .
C C2 0.87843(8) -0.1830(3) 0.51731(10) 0.0193(3) Uani d . . . 1 . .
H H20 0.853313 -0.32277 0.486661 0.023 Uiso calc U . R 1 . .
H H19 0.864783 -0.162166 0.566895 0.023 Uiso calc U . R 1 . .
C C3 0.79387(8) 0.0617(3) 0.42565(9) 0.0178(3) Uani d . . . 1 . .
C C4 0.78140(8) 0.2806(3) 0.37431(9) 0.0155(3) Uani d . . . 1 . .
C C5 0.83414(8) 0.3957(3) 0.35722(9) 0.0147(3) Uani d . . . 1 . .
H H4 0.880346 0.345712 0.383927 0.018 Uiso calc U . R 1 . .
C C6 0.82210(8) 0.5877(3) 0.30082(9) 0.0147(3) Uani d . . . 1 . .
C C7 0.75442(8) 0.6462(3) 0.25845(9) 0.0139(3) Uani d . . . 1 . .
C C8 0.73356(7) 0.8390(3) 0.19333(9) 0.0137(3) Uani d . . . 1 . .
C C9 0.70445(8) 0.9108(3) 0.05087(9) 0.0198(3) Uani d . . . 1 . .
H H15 0.732584 0.892815 0.014006 0.024 Uiso calc U . R 1 . .
H H18 0.707816 1.079229 0.069632 0.024 Uiso calc U . R 1 . .
C C10 0.63057(10) 0.8491(4) 0.00645(13) 0.0384(5) Uani d . . . 1 . .
H H2 0.627311 0.679967 -0.009459 0.058 Uiso calc U . R 1 . .
H H17 0.613575 0.949156 -0.042377 0.058 Uiso calc U . R 1 . .
H H16 0.602482 0.877711 0.042117 0.058 Uiso calc U . R 1 . .
C C11 0.88273(8) 0.7104(3) 0.29040(9) 0.0148(3) Uani d . . . 1 . .
C C12 0.92103(8) 1.0333(3) 0.22596(10) 0.0199(3) Uani d . . . 1 . .
H H5 0.95447 0.929789 0.210935 0.024 Uiso calc U . R 1 . .
H H9 0.945778 1.119159 0.276952 0.024 Uiso calc U . R 1 . .
C C13 0.88849(8) 1.2094(3) 0.15860(10) 0.0212(3) Uani d . . . 1 . .
H H6 0.866416 1.122202 0.107824 0.032 Uiso calc U . R 1 . .
H H7 0.924246 1.315839 0.151266 0.032 Uiso calc U . R 1 . .
H H8 0.85367 1.304463 0.172942 0.032 Uiso calc U . R 1 . .
C C14 0.71008(8) 0.3596(3) 0.33741(9) 0.0152(3) Uani d . . . 1 . .
C C15 0.62979(7) 0.5843(3) 0.22579(9) 0.0151(3) Uani d . . . 1 . .
C C16 0.59874(8) 0.4266(3) 0.16334(10) 0.0194(3) Uani d . . . 1 . .
H H14 0.623764 0.294336 0.152504 0.023 Uiso calc U . R 1 . .
C C17 0.53012(8) 0.4651(3) 0.11656(10) 0.0221(4) Uani d . . . 1 . .
H H13 0.507895 0.357771 0.073632 0.027 Uiso calc U . R 1 . .
C C18 0.49419(8) 0.6594(3) 0.13243(11) 0.0225(4) Uani d . . . 1 . .
H H10 0.447417 0.685218 0.100303 0.027 Uiso calc U . R 1 . .
C C19 0.52640(8) 0.8163(3) 0.19518(11) 0.0222(4) Uani d . . . 1 . .
H H11 0.501615 0.949839 0.205595 0.027 Uiso calc U . R 1 . .
C C20 0.59506(8) 0.7792(3) 0.24317(10) 0.0187(3) Uani d . . . 1 . .
H H12 0.617272 0.885026 0.286575 0.022 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 . 1.3520(19) ?
O1 C2 . 1.4530(19) ?
O2 C8 . 1.3264(18) ?
O2 C9 . 1.4735(18) ?
O3 C3 . 1.203(2) ?
O4 C11 . 1.2111(19) ?
O5 C11 . 1.3356(19) ?
O5 C12 . 1.4519(18) ?
O6 C14 . 1.2148(19) ?
O7 C8 . 1.1951(19) ?
N1 C7 . 1.3552(19) ?
N1 C14 . 1.431(2) ?
N1 C15 . 1.4589(18) ?
C1 C2 . 1.505(2) ?
C1 H1 . 0.98 ?
C1 H21 . 0.98 ?
C1 H3 . 0.98 ?
C2 H20 . 0.99 ?
C2 H19 . 0.99 ?
C3 C4 . 1.485(2) ?
C4 C5 . 1.364(2) ?
C4 C14 . 1.458(2) ?
C5 C6 . 1.418(2) ?
C5 H4 . 0.95 ?
C6 C7 . 1.380(2) ?
C6 C11 . 1.474(2) ?
C7 C8 . 1.518(2) ?
C9 C10 . 1.498(2) ?
C9 H15 . 0.99 ?
C9 H18 . 0.99 ?
C10 H2 . 0.98 ?
C10 H17 . 0.98 ?
C10 H16 . 0.98 ?
C12 C13 . 1.508(2) ?
C12 H5 . 0.99 ?
C12 H9 . 0.99 ?
C13 H6 . 0.98 ?
C13 H7 . 0.98 ?
C13 H8 . 0.98 ?
C15 C16 . 1.382(2) ?
C15 C20 . 1.383(2) ?
C16 C17 . 1.392(2) ?
C16 H14 . 0.95 ?
C17 C18 . 1.385(2) ?
C17 H13 . 0.95 ?
C18 C19 . 1.387(3) ?
C18 H10 . 0.95 ?
C19 C20 . 1.398(2) ?
C19 H11 . 0.95 ?
C20 H12 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 C2 . . 115.27(12) ?
C8 O2 C9 . . 116.33(12) ?
C11 O5 C12 . . 117.16(12) ?
C7 N1 C14 . . 123.67(12) ?
C7 N1 C15 . . 120.74(13) ?
C14 N1 C15 . . 115.52(12) ?
C2 C1 H1 . . 109.5 ?
C2 C1 H21 . . 109.5 ?
H1 C1 H21 . . 109.5 ?
C2 C1 H3 . . 109.5 ?
H1 C1 H3 . . 109.5 ?
H21 C1 H3 . . 109.5 ?
O1 C2 C1 . . 107.61(13) ?
O1 C2 H20 . . 110.2 ?
C1 C2 H20 . . 110.2 ?
O1 C2 H19 . . 110.2 ?
C1 C2 H19 . . 110.2 ?
H20 C2 H19 . . 108.5 ?
O3 C3 O1 . . 123.01(15) ?
O3 C3 C4 . . 124.95(15) ?
O1 C3 C4 . . 111.91(13) ?
C5 C4 C14 . . 120.52(14) ?
C5 C4 C3 . . 121.41(14) ?
C14 C4 C3 . . 117.91(14) ?
C4 C5 C6 . . 122.02(14) ?
C4 C5 H4 . . 119.0 ?
C6 C5 H4 . . 119.0 ?
C7 C6 C5 . . 118.00(14) ?
C7 C6 C11 . . 124.13(14) ?
C5 C6 C11 . . 117.87(13) ?
N1 C7 C6 . . 120.89(14) ?
N1 C7 C8 . . 115.11(13) ?
C6 C7 C8 . . 123.97(13) ?
O7 C8 O2 . . 127.37(14) ?
O7 C8 C7 . . 122.21(13) ?
O2 C8 C7 . . 110.40(12) ?
O2 C9 C10 . . 108.89(14) ?
O2 C9 H15 . . 109.9 ?
C10 C9 H15 . . 109.9 ?
O2 C9 H18 . . 109.9 ?
C10 C9 H18 . . 109.9 ?
H15 C9 H18 . . 108.3 ?
C9 C10 H2 . . 109.5 ?
C9 C10 H17 . . 109.5 ?
H2 C10 H17 . . 109.5 ?
C9 C10 H16 . . 109.5 ?
H2 C10 H16 . . 109.5 ?
H17 C10 H16 . . 109.5 ?
O4 C11 O5 . . 123.46(14) ?
O4 C11 C6 . . 123.92(14) ?
O5 C11 C6 . . 112.61(13) ?
O5 C12 C13 . . 106.82(12) ?
O5 C12 H5 . . 110.4 ?
C13 C12 H5 . . 110.4 ?
O5 C12 H9 . . 110.4 ?
C13 C12 H9 . . 110.4 ?
H5 C12 H9 . . 108.6 ?
C12 C13 H6 . . 109.5 ?
C12 C13 H7 . . 109.5 ?
H6 C13 H7 . . 109.5 ?
C12 C13 H8 . . 109.5 ?
H6 C13 H8 . . 109.5 ?
H7 C13 H8 . . 109.5 ?
O6 C14 N1 . . 118.96(14) ?
O6 C14 C4 . . 126.95(15) ?
N1 C14 C4 . . 114.09(13) ?
C16 C15 C20 . . 122.19(14) ?
C16 C15 N1 . . 117.56(13) ?
C20 C15 N1 . . 120.23(14) ?
C15 C16 C17 . . 118.82(15) ?
C15 C16 H14 . . 120.6 ?
C17 C16 H14 . . 120.6 ?
C18 C17 C16 . . 120.19(16) ?
C18 C17 H13 . . 119.9 ?
C16 C17 H13 . . 119.9 ?
C17 C18 C19 . . 120.10(15) ?
C17 C18 H10 . . 119.9 ?
C19 C18 H10 . . 119.9 ?
C18 C19 C20 . . 120.46(15) ?
C18 C19 H11 . . 119.8 ?
C20 C19 H11 . . 119.8 ?
C15 C20 C19 . . 118.23(15) ?
C15 C20 H12 . . 120.9 ?
C19 C20 H12 . . 120.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 O1 C2 C1 . . . . 165.21(14) ?
C2 O1 C3 O3 . . . . -2.4(2) ?
C2 O1 C3 C4 . . . . -178.54(12) ?
O3 C3 C4 C5 . . . . -161.00(16) ?
O1 C3 C4 C5 . . . . 15.1(2) ?
O3 C3 C4 C14 . . . . 14.5(2) ?
O1 C3 C4 C14 . . . . -169.43(13) ?
C14 C4 C5 C6 . . . . -2.9(2) ?
C3 C4 C5 C6 . . . . 172.49(14) ?
C4 C5 C6 C7 . . . . -4.5(2) ?
C4 C5 C6 C11 . . . . 176.22(14) ?
C14 N1 C7 C6 . . . . 1.8(2) ?
C15 N1 C7 C6 . . . . -175.05(14) ?
C14 N1 C7 C8 . . . . -176.33(13) ?
C15 N1 C7 C8 . . . . 6.87(19) ?
C5 C6 C7 N1 . . . . 5.1(2) ?
C11 C6 C7 N1 . . . . -175.65(13) ?
C5 C6 C7 C8 . . . . -176.95(13) ?
C11 C6 C7 C8 . . . . 2.2(2) ?
C9 O2 C8 O7 . . . . -3.9(2) ?
C9 O2 C8 C7 . . . . 174.34(12) ?
N1 C7 C8 O7 . . . . 82.97(18) ?
C6 C7 C8 O7 . . . . -95.05(19) ?
N1 C7 C8 O2 . . . . -95.36(15) ?
C6 C7 C8 O2 . . . . 86.63(17) ?
C8 O2 C9 C10 . . . . -101.11(17) ?
C12 O5 C11 O4 . . . . -3.1(2) ?
C12 O5 C11 C6 . . . . 176.12(13) ?
C7 C6 C11 O4 . . . . -178.95(15) ?
C5 C6 C11 O4 . . . . 0.3(2) ?
C7 C6 C11 O5 . . . . 1.9(2) ?
C5 C6 C11 O5 . . . . -178.93(13) ?
C11 O5 C12 C13 . . . . 175.62(13) ?
C7 N1 C14 O6 . . . . 171.20(14) ?
C15 N1 C14 O6 . . . . -11.8(2) ?
C7 N1 C14 C4 . . . . -8.7(2) ?
C15 N1 C14 C4 . . . . 168.26(13) ?
C5 C4 C14 O6 . . . . -170.83(15) ?
C3 C4 C14 O6 . . . . 13.6(2) ?
C5 C4 C14 N1 . . . . 9.1(2) ?
C3 C4 C14 N1 . . . . -166.48(13) ?
C7 N1 C15 C16 . . . . 96.46(17) ?
C14 N1 C15 C16 . . . . -80.59(17) ?
C7 N1 C15 C20 . . . . -84.75(18) ?
C14 N1 C15 C20 . . . . 98.19(17) ?
C20 C15 C16 C17 . . . . -0.2(2) ?
N1 C15 C16 C17 . . . . 178.56(14) ?
C15 C16 C17 C18 . . . . 0.4(3) ?
C16 C17 C18 C19 . . . . -0.1(3) ?
C17 C18 C19 C20 . . . . -0.4(3) ?
C16 C15 C20 C19 . . . . -0.3(2) ?
N1 C15 C20 C19 . . . . -179.06(14) ?
C18 C19 C20 C15 . . . . 0.6(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H21 O4 3_756 0.98 2.63 3.535(2) 153.5 ?
C9 H15 O3 4_565 0.99 2.40 3.177(2) 135.2 ?
C16 H14 O7 1_545 0.95 2.38 3.1988(19) 144.7 ?
C20 H12 O6 1_565 0.95 2.58 3.468(2) 156.3 ?

