# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_2103191533
_database_code_depnum_ccdc_archive 'CCDC 2081693'
loop_
_audit_author_name
_audit_author_address
'Yanqing Ge'
;shandong first medical university
China
;
_audit_update_record             
;
2021-05-04 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C26 H26 N2 O10)'
_chemical_formula_sum            'C13 H13 N O5'
_chemical_formula_weight         263.24
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   10.1584(2)
_cell_length_b                   6.6612(2)
_cell_length_c                   18.5993(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1258.56(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8438
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.98
_cell_measurement_theta_min      4.32
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.2155 before and 0.0908 after correction. The Ratio of minimum to maximum transmission is 0.5727. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10576
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.960
_diffrn_reflns_theta_min         4.314
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1144
_reflns_number_total             1306
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.099
_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)+(0.0737P)²+0.5268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1573
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H10C(0.5) H12A(0.5) H12B(0.5) H13B(0.5)
 H13C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.b Me refined with riding coordinates:
 C13(H13A,H13B,H13C)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C8(H8)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.4576(2) 0.750000 0.31845(11) 0.0754(7) Uani 1 2 d S T P . .
O2 O 0.25835(19) 0.750000 0.37002(11) 0.0634(6) Uani 1 2 d S T P . .
O3 O 0.9053(2) 0.750000 0.40196(13) 0.0759(8) Uani 1 2 d S T P . .
O4 O 1.0497(2) 0.750000 0.51690(13) 0.0962(10) Uani 1 2 d S T P . .
O5 O 0.95583(19) 0.750000 0.62467(11) 0.0673(7) Uani 1 2 d S T P . .
N1 N 0.56974(19) 0.750000 0.46240(11) 0.0421(5) Uani 1 2 d S T P . .
C1 C 0.4376(2) 0.750000 0.44529(14) 0.0439(6) Uani 1 2 d S T P . .
C2 C 0.3677(2) 0.750000 0.50960(14) 0.0476(7) Uani 1 2 d S T P . .
H2 H 0.274471 0.750000 0.513750 0.057 Uiso 1 2 calc RS T P . .
C3 C 0.4542(2) 0.750000 0.56595(15) 0.0477(7) Uani 1 2 d S T P . .
H3A H 0.431880 0.750000 0.615550 0.057 Uiso 1 2 calc RS T P . .
C4 C 0.5819(2) 0.750000 0.53727(14) 0.0425(6) Uani 1 2 d S T P . .
C5 C 0.7076(2) 0.750000 0.56667(15) 0.0463(6) Uani 1 2 d S T P . .
H5 H 0.717583 0.750000 0.617455 0.056 Uiso 1 2 calc RS T P . .
C6 C 0.8175(2) 0.750000 0.52392(16) 0.0512(7) Uani 1 2 d S T P . .
C7 C 0.8006(3) 0.750000 0.44795(16) 0.0551(7) Uani 1 2 d S T P . .
C8 C 0.6787(3) 0.750000 0.41841(15) 0.0516(7) Uani 1 2 d S T P . .
H8 H 0.668461 0.750000 0.367638 0.062 Uiso 1 2 calc RS T P . .
C9 C 0.3906(3) 0.750000 0.37214(15) 0.0515(7) Uani 1 2 d S T P . .
C10 C 0.1990(3) 0.750000 0.29992(18) 0.0764(11) Uani 1 2 d S T P . .
H10A H 0.107618 0.703929 0.303651 0.115 Uiso 0.5 1 calc GR . . A -1
H10B H 0.248161 0.659732 0.268146 0.115 Uiso 0.5 1 calc GR . . A -1
H10C H 0.200669 0.886339 0.280143 0.115 Uiso 0.5 1 calc GR . . A -1
C11 C 0.9511(3) 0.750000 0.55389(17) 0.0640(9) Uani 1 2 d S T P . .
C12 C 1.0884(3) 0.750000 0.65581(19) 0.0828(12) Uani 1 2 d S T P . .
H12A H 1.137501 0.629393 0.640013 0.099 Uiso 0.5 1 calc R . . . .
H12B H 1.137502 0.870607 0.640013 0.099 Uiso 0.5 1 calc R . . . .
C13 C 1.0744(4) 0.750000 0.7330(2) 0.0924(13) Uani 1 2 d S T P . .
H13A H 1.161685 0.750000 0.755432 0.139 Uiso 0.5 1 calc RS T P B -1
H13B H 1.025924 0.870124 0.748048 0.139 Uiso 0.5 1 calc R . . B -1
H13C H 1.025924 0.629876 0.748048 0.139 Uiso 0.5 1 calc R . . B -1
H3 H 0.974(4) 0.750000 0.433(2) 0.093(13) Uiso 1 2 d S T P . .


_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
O1 C9 1.209(4) . ?
O2 C9 1.343(3) . ?
O2 C10 1.437(4) . ?
O3 C7 1.364(3) . ?
O3 H3 0.91(4) . ?
O4 C11 1.216(4) . ?
O5 C11 1.317(4) . ?
O5 C12 1.466(3) . ?
N1 C1 1.380(3) . ?
N1 C4 1.398(3) . ?
N1 C8 1.376(3) . ?
C1 C2 1.391(4) . ?
C1 C9 1.442(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.368(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.403(3) . ?
C4 C5 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.370(4) . ?
C6 C7 1.423(4) . ?
C6 C11 1.467(4) . ?
C7 C8 1.355(4) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.443(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C9 O2 C10 116.5(2) . . ?
C7 O3 H3 101(3) . . ?
C11 O5 C12 115.4(2) . . ?
C1 N1 C4 108.4(2) . . ?
C8 N1 C1 130.2(2) . . ?
C8 N1 C4 121.4(2) . . ?
N1 C1 C2 107.3(2) . . ?
N1 C1 C9 122.7(2) . . ?
C2 C1 C9 130.0(2) . . ?
C1 C2 H2 125.3 . . ?
C3 C2 C1 109.3(2) . . ?
C3 C2 H2 125.3 . . ?
C2 C3 H3A 126.2 . . ?
C2 C3 C4 107.6(2) . . ?
C4 C3 H3A 126.2 . . ?
N1 C4 C3 107.3(2) . . ?
C5 C4 N1 118.3(2) . . ?
C5 C4 C3 134.5(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 118.6(2) . . ?
C5 C6 C11 122.2(3) . . ?
C7 C6 C11 119.2(2) . . ?
O3 C7 C6 121.9(2) . . ?
C8 C7 O3 117.3(3) . . ?
C8 C7 C6 120.8(2) . . ?
N1 C8 H8 120.2 . . ?
C7 C8 N1 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
O1 C9 O2 122.6(3) . . ?
O1 C9 C1 126.4(3) . . ?
O2 C9 C1 111.0(2) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 O5 122.4(3) . . ?
O4 C11 C6 123.2(3) . . ?
O5 C11 C6 114.4(2) . . ?
O5 C12 H12A 110.2 . . ?
O5 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 O5 107.6(3) . . ?
C13 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O4 0.91(4) 1.74(4) 2.593(3) 156(4) .

_olex2_submission_special_instructions 'No special instructions were received'
