# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_WXW20180522
_audit_block_doi                 10.5517/ccdc.csd.cc24t7mv
_database_code_depnum_ccdc_archive 'CCDC 1990467'
loop_
_audit_author_name
_audit_author_address
'Zhenming Zhang'
;Jiangxi normal univeristy
China
;
_audit_update_record             
;
2020-03-15 deposited with the CCDC.	2020-09-09 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            'C25 H22 N2 O8'
_chemical_formula_weight         478.44

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1947(4)
_cell_length_b                   22.1997(8)
_cell_length_c                   12.9203(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.070(4)
_cell_angle_gamma                90
_cell_volume                     2298.50(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7547
_cell_measurement_theta_min      3.8550
_cell_measurement_theta_max      26.9360

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_T_min  0.77395
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.37b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21510
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.283
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4693
_reflns_number_gt                3726
_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       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0723P)²+1.3409P] 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         4693
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
O3 O 0.71978(18) 0.28266(6) 0.23323(11) 0.0413(4) Uani 1 1 d . . . . .
O2 O 0.4120(2) 0.34228(7) 0.24656(14) 0.0529(4) Uani 1 1 d . . . . .
O4 O 0.5498(2) 0.20221(7) 0.22826(13) 0.0575(5) Uani 1 1 d . . . . .
O8 O 0.8259(3) 0.40386(8) 0.55452(15) 0.0682(5) Uani 1 1 d . . . . .
O7 O 0.7287(3) 0.37494(9) 0.68786(14) 0.0749(6) Uani 1 1 d . . . . .
N2 N 0.7609(3) 0.36655(9) 0.60150(16) 0.0524(5) Uani 1 1 d . . . . .
O6 O 0.5481(2) 0.16743(11) 0.70435(15) 0.0770(6) Uani 1 1 d . . . . .
O1 O 0.4137(3) 0.40058(11) 0.48106(16) 0.0807(6) Uani 1 1 d . . . . .
N1 N 0.5853(3) 0.15687(11) 0.61993(18) 0.0629(6) Uani 1 1 d . . . . .
C20 C 0.6612(3) 0.24830(9) 0.39333(16) 0.0385(4) Uani 1 1 d . . . . .
C19 C 0.6357(3) 0.24071(9) 0.27682(16) 0.0398(5) Uani 1 1 d . . . . .
O5 O 0.5900(4) 0.10659(10) 0.58262(17) 0.1004(9) Uani 1 1 d . . . . .
C24 C 0.7169(3) 0.30792(9) 0.54993(17) 0.0419(5) Uani 1 1 d . . . . .
C25 C 0.7148(3) 0.30230(9) 0.44357(16) 0.0407(5) Uani 1 1 d . . . . .
H25 H 0.7485 0.3340 0.4060 0.049 Uiso 1 1 calc R U . . .
C11 C 0.5928(3) 0.39294(9) 0.15017(16) 0.0419(5) Uani 1 1 d . . . . .
C18 C 0.6838(3) 0.28758(9) 0.12209(16) 0.0418(5) Uani 1 1 d . . . . .
C12 C 0.4925(3) 0.38627(9) 0.23156(16) 0.0405(5) Uani 1 1 d . . . . .
C13 C 0.6242(3) 0.34299(9) 0.08112(17) 0.0440(5) Uani 1 1 d . . . . .
C22 C 0.6288(3) 0.20790(10) 0.55817(17) 0.0450(5) Uani 1 1 d . . . . .
C21 C 0.6177(3) 0.20045(9) 0.45132(17) 0.0428(5) Uani 1 1 d . . . . .
H21 H 0.5818 0.1641 0.4185 0.051 Uiso 1 1 calc R U . . .
C10 C 0.6396(3) 0.45086(10) 0.14640(17) 0.0454(5) Uani 1 1 d . . . . .
C4 C 0.5041(3) 0.44431(10) 0.29386(17) 0.0458(5) Uani 1 1 d . . . . .
H4 H 0.5875 0.4381 0.3594 0.055 Uiso 1 1 calc R U . . .
C23 C 0.6750(3) 0.26134(10) 0.60975(17) 0.0468(5) Uani 1 1 d . . . . .
H23 H 0.6778 0.2658 0.6817 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5784(3) 0.48943(10) 0.22658(18) 0.0482(5) Uani 1 1 d . . . . .
H5 H 0.4880 0.5151 0.1888 0.058 Uiso 1 1 calc R U . . .
C17 C 0.7185(3) 0.24107(11) 0.05966(19) 0.0558(6) Uani 1 1 d . . . . .
H17 H 0.7607 0.2048 0.0899 0.067 Uiso 1 1 calc R U . . .
C2 C 0.3069(3) 0.42609(12) 0.4182(2) 0.0579(6) Uani 1 1 d . . . . .
C9 C 0.7436(4) 0.48014(11) 0.0787(2) 0.0607(7) Uani 1 1 d . . . . .
H9A H 0.6733 0.5052 0.0260 0.073 Uiso 1 1 calc R U . . .
H9B H 0.7940 0.4495 0.0421 0.073 Uiso 1 1 calc R U . . .
C3 C 0.3431(3) 0.46126(12) 0.3253(2) 0.0599(7) Uani 1 1 d . . . . .
H3A H 0.3467 0.5038 0.3427 0.072 Uiso 1 1 calc R U . . .
H3B H 0.2519 0.4552 0.2650 0.072 Uiso 1 1 calc R U . . .
C14 C 0.5960(4) 0.34933(12) -0.02834(19) 0.0625(7) Uani 1 1 d . . . . .
H14 H 0.5552 0.3857 -0.0591 0.075 Uiso 1 1 calc R U . . .
C16 C 0.6893(4) 0.24917(13) -0.0490(2) 0.0706(8) Uani 1 1 d . . . . .
H16 H 0.7118 0.2183 -0.0926 0.085 Uiso 1 1 calc R U . . .
C6 C 0.7150(4) 0.52963(12) 0.2870(2) 0.0667(7) Uani 1 1 d . . . . .
H6A H 0.7932 0.5053 0.3365 0.080 Uiso 1 1 calc R U . . .
H6B H 0.6662 0.5588 0.3274 0.080 Uiso 1 1 calc R U . . .
C8 C 0.8794(4) 0.51852(13) 0.1454(3) 0.0710(8) Uani 1 1 d . . . . .
H8A H 0.9599 0.4925 0.1899 0.085 Uiso 1 1 calc R U . . .
H8B H 0.9371 0.5407 0.0992 0.085 Uiso 1 1 calc R U . . .
C1 C 0.1307(4) 0.42608(16) 0.4287(2) 0.0750(8) Uani 1 1 d . . . . .
H1A H 0.1204 0.4035 0.4904 0.112 Uiso 1 1 calc R U . . .
H1B H 0.0626 0.4080 0.3670 0.112 Uiso 1 1 calc R U . . .
H1C H 0.0947 0.4668 0.4355 0.112 Uiso 1 1 calc R U . . .
C15 C 0.6273(5) 0.30297(14) -0.0918(2) 0.0775(9) Uani 1 1 d . . . . .
H15 H 0.6061 0.3082 -0.1648 0.093 Uiso 1 1 calc R U . . .
C7 C 0.8085(4) 0.56272(13) 0.2147(3) 0.0762(9) Uani 1 1 d . . . . .
H7A H 0.8988 0.5859 0.2571 0.091 Uiso 1 1 calc R U . . .
H7B H 0.7336 0.5905 0.1703 0.091 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
O3 C19 1.350(2) . ?
O3 C18 1.408(2) . ?
O2 C12 1.216(3) . ?
O4 C19 1.198(3) . ?
O8 N2 1.214(3) . ?
O7 N2 1.214(3) . ?
N2 C24 1.472(3) . ?
O6 N1 1.215(3) . ?
O1 C2 1.204(3) . ?
N1 O5 1.220(3) . ?
N1 C22 1.472(3) . ?
C20 C21 1.388(3) . ?
C20 C25 1.390(3) . ?
C20 C19 1.486(3) . ?
C24 C23 1.377(3) . ?
C24 C25 1.376(3) . ?
C25 H25 0.9300 . ?
C11 C10 1.345(3) . ?
C11 C12 1.471(3) . ?
C11 C13 1.479(3) . ?
C18 C17 1.376(3) . ?
C18 C13 1.387(3) . ?
C12 C4 1.512(3) . ?
C13 C14 1.392(3) . ?
C22 C23 1.374(3) . ?
C22 C21 1.374(3) . ?
C21 H21 0.9300 . ?
C10 C9 1.491(3) . ?
C10 C5 1.508(3) . ?
C4 C3 1.507(3) . ?
C4 C5 1.533(3) . ?
C4 H4 0.9800 . ?
C23 H23 0.9300 . ?
C5 C6 1.514(4) . ?
C5 H5 0.9800 . ?
C17 C16 1.386(4) . ?
C17 H17 0.9300 . ?
C2 C1 1.478(4) . ?
C2 C3 1.513(4) . ?
C9 C8 1.518(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C14 C15 1.373(4) . ?
C14 H14 0.9300 . ?
C16 C15 1.368(4) . ?
C16 H16 0.9300 . ?
C6 C7 1.515(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C7 1.523(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C15 H15 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
C19 O3 C18 117.55(16) . . ?
O7 N2 O8 123.9(2) . . ?
O7 N2 C24 118.2(2) . . ?
O8 N2 C24 117.94(19) . . ?
O6 N1 O5 124.5(2) . . ?
O6 N1 C22 118.2(2) . . ?
O5 N1 C22 117.3(2) . . ?
C21 C20 C25 119.96(19) . . ?
C21 C20 C19 117.55(18) . . ?
C25 C20 C19 122.33(18) . . ?
O4 C19 O3 124.68(19) . . ?
O4 C19 C20 123.68(19) . . ?
O3 C19 C20 111.63(17) . . ?
C23 C24 C25 122.7(2) . . ?
C23 C24 N2 118.44(19) . . ?
C25 C24 N2 118.86(19) . . ?
C24 C25 C20 118.76(19) . . ?
C24 C25 H25 120.6 . . ?
C20 C25 H25 120.6 . . ?
C10 C11 C12 109.16(19) . . ?
C10 C11 C13 127.4(2) . . ?
C12 C11 C13 123.30(18) . . ?
C17 C18 C13 122.8(2) . . ?
C17 C18 O3 121.0(2) . . ?
C13 C18 O3 116.09(17) . . ?
O2 C12 C11 126.68(19) . . ?
O2 C12 C4 125.12(19) . . ?
C11 C12 C4 108.20(18) . . ?
C18 C13 C14 116.6(2) . . ?
C18 C13 C11 121.77(19) . . ?
C14 C13 C11 121.6(2) . . ?
C23 C22 C21 122.99(19) . . ?
C23 C22 N1 118.3(2) . . ?
C21 C22 N1 118.6(2) . . ?
C22 C21 C20 118.6(2) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C11 C10 C9 129.8(2) . . ?
C11 C10 C5 112.3(2) . . ?
C9 C10 C5 117.90(19) . . ?
C3 C4 C12 113.3(2) . . ?
C3 C4 C5 117.60(19) . . ?
C12 C4 C5 104.08(17) . . ?
C3 C4 H4 107.1 . . ?
C12 C4 H4 107.1 . . ?
C5 C4 H4 107.1 . . ?
C24 C23 C22 116.9(2) . . ?
C24 C23 H23 121.6 . . ?
C22 C23 H23 121.6 . . ?
C10 C5 C6 111.8(2) . . ?
C10 C5 C4 104.29(17) . . ?
C6 C5 C4 115.6(2) . . ?
C10 C5 H5 108.3 . . ?
C6 C5 H5 108.3 . . ?
C4 C5 H5 108.3 . . ?
C18 C17 C16 118.9(2) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
O1 C2 C1 121.6(3) . . ?
O1 C2 C3 122.8(2) . . ?
C1 C2 C3 115.5(2) . . ?
C10 C9 C8 110.7(2) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C2 C3 C4 114.4(2) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C15 C16 C17 119.5(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C5 C6 C7 112.5(2) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C7 C8 C9 111.8(2) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C6 C7 C8 110.7(2) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038



