# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_190721d
_database_code_depnum_ccdc_archive 'CCDC 1956080'
loop_
_audit_author_name
_audit_author_address
'zheng jing'
;nanchang university
China
;
_audit_update_record             
;
2020-03-19 deposited with the CCDC.	2020-05-29 downloaded from the CCDC.
;
_audit_creation_date             2020-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H24 O7'
_chemical_formula_sum            'C25 H24 O7'
_chemical_formula_weight         436.44
_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 0.0033 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'
O O 0.0106 0.0060 '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           14
_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                   18.8673(16)
_cell_length_b                   10.1312(9)
_cell_length_c                   11.7065(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.297(3)
_cell_angle_gamma                90
_cell_volume                     2158.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1521
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.138
_cell_measurement_theta_min      2.238
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1011
_diffrn_reflns_av_unetI/netI     0.1172
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13474
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2079
_reflns_number_total             5373
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1674
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      0.881
_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)+(0.0517P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1586
_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.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.08079(9) 0.81675(18) 1.01913(17) 0.0604(5) Uani 1 1 d . . . . .
O2 O 0.13511(10) 1.03812(19) 0.69331(18) 0.0683(6) Uani 1 1 d . . . . .
O3 O 0.28980(10) 0.56537(19) 0.96547(17) 0.0671(6) Uani 1 1 d . . . . .
O4 O 0.28904(11) 0.7111(2) 0.82118(18) 0.0715(6) Uani 1 1 d . . . . .
O5 O 0.37096(9) 0.90397(18) 1.03088(16) 0.0570(5) Uani 1 1 d . . . . .
O6 O 0.44716(10) 1.10566(19) 1.17523(18) 0.0672(6) Uani 1 1 d . . . . .
O7 O 0.37582(10) 1.3153(2) 1.22717(19) 0.0715(6) Uani 1 1 d . . . . .
C1 C 0.27395(14) 0.6831(3) 0.9121(3) 0.0539(7) Uani 1 1 d . . . . .
C2 C 0.23351(13) 0.7713(3) 0.9748(2) 0.0487(7) Uani 1 1 d . . . . .
C3 C 0.20392(14) 0.7266(3) 1.0585(2) 0.0525(7) Uani 1 1 d . . . . .
H3 H 0.2157 0.6420 1.0883 0.063 Uiso 1 1 calc R . . . .
C4 C 0.15228(14) 0.8083(3) 1.1058(2) 0.0568(7) Uani 1 1 d . . . . .
H4A H 0.1464 0.7692 1.1784 0.068 Uiso 1 1 calc R . . . .
H4B H 0.1724 0.8962 1.1240 0.068 Uiso 1 1 calc R . . . .
C5 C 0.08092(15) 0.8797(3) 0.9182(2) 0.0514(7) Uani 1 1 d . . . . .
C6 C 0.00857(14) 0.8974(3) 0.8307(3) 0.0546(7) Uani 1 1 d . . . . .
C7 C -0.06062(15) 0.8543(3) 0.8305(3) 0.0660(8) Uani 1 1 d . . . . .
H7 H -0.0688 0.8083 0.8946 0.079 Uiso 1 1 calc R . . . .
C8 C -0.11789(16) 0.8820(3) 0.7312(3) 0.0761(9) Uani 1 1 d . . . . .
H8 H -0.1649 0.8516 0.7280 0.091 Uiso 1 1 calc R . . . .
C9 C -0.10644(17) 0.9531(3) 0.6377(3) 0.0795(10) Uani 1 1 d . . . . .
H9 H -0.1459 0.9719 0.5731 0.095 Uiso 1 1 calc R . . . .
C10 C -0.03637(17) 0.9974(3) 0.6388(3) 0.0688(8) Uani 1 1 d . . . . .
H10 H -0.0284 1.0459 0.5759 0.083 Uiso 1 1 calc R . . . .
C11 C 0.02057(15) 0.9676(3) 0.7354(3) 0.0555(7) Uani 1 1 d . . . . .
C12 C 0.10265(14) 0.9881(3) 0.7603(3) 0.0529(7) Uani 1 1 d . . . . .
C13 C 0.13631(14) 0.9280(3) 0.8765(2) 0.0511(7) Uani 1 1 d . . . . .
C14 C 0.21839(13) 0.9110(3) 0.9245(2) 0.0490(7) Uani 1 1 d . . . . .
H14 H 0.2387 0.9144 0.8556 0.059 Uiso 1 1 calc R . . . .
C15 C 0.25814(13) 1.0192(3) 1.0090(2) 0.0465(6) Uani 1 1 d . . . . .
C16 C 0.33373(14) 1.0113(3) 1.0590(2) 0.0487(7) Uani 1 1 d . . . . .
C17 C 0.37166(14) 1.1130(3) 1.1285(2) 0.0522(7) Uani 1 1 d . . . . .
C18 C 0.33349(15) 1.2230(3) 1.1550(2) 0.0530(7) Uani 1 1 d . . . . .
C19 C 0.25849(15) 1.2311(3) 1.1062(2) 0.0572(8) Uani 1 1 d . . . . .
H19 H 0.2324 1.3036 1.1221 0.069 Uiso 1 1 calc R . . . .
C20 C 0.22224(14) 1.1305(3) 1.0332(2) 0.0541(7) Uani 1 1 d . . . . .
H20 H 0.1720 1.1383 0.9994 0.065 Uiso 1 1 calc R . . . .
C21 C 0.32479(17) 0.4681(3) 0.9042(3) 0.0744(9) Uani 1 1 d . . . . .
H21A H 0.3121 0.3796 0.9233 0.089 Uiso 1 1 calc R . . . .
H21B H 0.3069 0.4801 0.8192 0.089 Uiso 1 1 calc R . . . .
C22 C 0.40492(17) 0.4845(4) 0.9405(3) 0.0911(11) Uani 1 1 d . . . . .
H22A H 0.4178 0.5669 0.9109 0.137 Uiso 1 1 calc GR . . . .
H22B H 0.4276 0.4133 0.9090 0.137 Uiso 1 1 calc GR . . . .
H22C H 0.4218 0.4839 1.0254 0.137 Uiso 1 1 calc GR . . . .
C23 C 0.41020(16) 0.8248(3) 1.1302(3) 0.0698(9) Uani 1 1 d . . . . .
H23A H 0.4537 0.8707 1.1727 0.105 Uiso 1 1 calc GR . . . .
H23B H 0.4238 0.7421 1.1019 0.105 Uiso 1 1 calc GR . . . .
H23C H 0.3792 0.8088 1.1820 0.105 Uiso 1 1 calc GR . . . .
C24 C 0.48753(17) 1.1635(4) 1.1015(3) 0.0963(12) Uani 1 1 d . . . . .
H24A H 0.4748 1.1208 1.0256 0.144 Uiso 1 1 calc GR . . . .
H24B H 0.5392 1.1532 1.1375 0.144 Uiso 1 1 calc GR . . . .
H24C H 0.4759 1.2558 1.0916 0.144 Uiso 1 1 calc GR . . . .
C25 C 0.33884(19) 1.4249(3) 1.2613(3) 0.0842(10) Uani 1 1 d . . . . .
H25A H 0.3137 1.4735 1.1921 0.126 Uiso 1 1 calc GR . . . .
H25B H 0.3740 1.4813 1.3131 0.126 Uiso 1 1 calc GR . . . .
H25C H 0.3039 1.3938 1.3017 0.126 Uiso 1 1 calc GR . . . .


_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 C4 1.461(3) . ?
O1 C5 1.343(3) . ?
O2 C12 1.225(3) . ?
O3 C1 1.343(3) . ?
O3 C21 1.473(3) . ?
O4 C1 1.206(3) . ?
O5 C16 1.381(3) . ?
O5 C23 1.445(3) . ?
O6 C17 1.387(3) . ?
O6 C24 1.420(4) . ?
O7 C18 1.367(3) . ?
O7 C25 1.424(3) . ?
C1 C2 1.488(4) . ?
C2 C3 1.329(3) . ?
C2 C14 1.531(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.492(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.486(4) . ?
C5 C13 1.356(3) . ?
C6 C7 1.376(4) . ?
C6 C11 1.392(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.393(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(4) . ?
C11 C12 1.513(4) . ?
C12 C13 1.473(4) . ?
C13 C14 1.511(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.533(4) . ?
C15 C16 1.394(3) . ?
C15 C20 1.383(3) . ?
C16 C17 1.389(4) . ?
C17 C18 1.405(4) . ?
C18 C19 1.382(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.468(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C5 O1 C4 115.0(2) . . ?
C1 O3 C21 116.1(2) . . ?
C16 O5 C23 115.5(2) . . ?
C17 O6 C24 113.4(2) . . ?
C18 O7 C25 117.2(2) . . ?
O3 C1 C2 112.6(2) . . ?
O4 C1 O3 123.0(3) . . ?
O4 C1 C2 124.4(3) . . ?
C1 C2 C14 115.7(2) . . ?
C3 C2 C1 121.9(3) . . ?
C3 C2 C14 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
O1 C4 C3 110.4(2) . . ?
O1 C4 H4A 109.6 . . ?
O1 C4 H4B 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
O1 C5 C6 116.7(2) . . ?
O1 C5 C13 131.9(3) . . ?
C13 C5 C6 111.3(2) . . ?
C7 C6 C5 131.4(3) . . ?
C7 C6 C11 121.1(3) . . ?
C11 C6 C5 107.5(2) . . ?
C6 C7 H7 121.1 . . ?
C6 C7 C8 117.7(3) . . ?
C8 C7 H7 121.1 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
C6 C11 C12 106.9(2) . . ?
C10 C11 C6 121.0(3) . . ?
C10 C11 C12 131.9(3) . . ?
O2 C12 C11 126.4(3) . . ?
O2 C12 C13 126.6(2) . . ?
C13 C12 C11 106.9(2) . . ?
C5 C13 C12 107.2(2) . . ?
C5 C13 C14 129.5(2) . . ?
C12 C13 C14 122.7(2) . . ?
C2 C14 H14 106.0 . . ?
C2 C14 C15 113.8(2) . . ?
C13 C14 C2 108.5(2) . . ?
C13 C14 H14 106.0 . . ?
C13 C14 C15 115.9(2) . . ?
C15 C14 H14 106.0 . . ?
C16 C15 C14 120.1(2) . . ?
C20 C15 C14 122.2(2) . . ?
C20 C15 C16 117.6(2) . . ?
O5 C16 C15 118.3(2) . . ?
O5 C16 C17 120.5(2) . . ?
C17 C16 C15 121.0(2) . . ?
O6 C17 C16 120.5(2) . . ?
O6 C17 C18 119.2(2) . . ?
C16 C17 C18 120.2(2) . . ?
O7 C18 C17 115.4(2) . . ?
O7 C18 C19 125.6(3) . . ?
C19 C18 C17 118.9(3) . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 122.4(2) . . ?
C15 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
O3 C21 H21A 109.6 . . ?
O3 C21 H21B 109.6 . . ?
H21A C21 H21B 108.2 . . ?
C22 C21 O3 110.1(3) . . ?
C22 C21 H21A 109.6 . . ?
C22 C21 H21B 109.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O7 C25 H25A 109.5 . . ?
O7 C25 H25B 109.5 . . ?
O7 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
O1 C5 C6 C7 -4.0(4) . . . . ?
O1 C5 C6 C11 178.2(2) . . . . ?
O1 C5 C13 C12 -179.5(3) . . . . ?
O1 C5 C13 C14 8.9(5) . . . . ?
O2 C12 C13 C5 -177.3(3) . . . . ?
O2 C12 C13 C14 -5.0(4) . . . . ?
O3 C1 C2 C3 -13.0(4) . . . . ?
O3 C1 C2 C14 175.7(2) . . . . ?
O4 C1 C2 C3 164.6(3) . . . . ?
O4 C1 C2 C14 -6.7(4) . . . . ?
O5 C16 C17 O6 -3.0(4) . . . . ?
O5 C16 C17 C18 178.9(2) . . . . ?
O6 C17 C18 O7 -0.2(4) . . . . ?
O6 C17 C18 C19 178.7(2) . . . . ?
O7 C18 C19 C20 179.4(3) . . . . ?
C1 O3 C21 C22 87.9(3) . . . . ?
C1 C2 C3 C4 -168.8(2) . . . . ?
C1 C2 C14 C13 114.6(2) . . . . ?
C1 C2 C14 C15 -114.8(2) . . . . ?
C2 C3 C4 O1 73.6(3) . . . . ?
C2 C14 C15 C16 52.4(3) . . . . ?
C2 C14 C15 C20 -131.4(2) . . . . ?
C3 C2 C14 C13 -56.7(3) . . . . ?
C3 C2 C14 C15 73.9(3) . . . . ?
C4 O1 C5 C6 -176.5(2) . . . . ?
C4 O1 C5 C13 6.4(4) . . . . ?
C5 O1 C4 C3 -64.6(3) . . . . ?
C5 C6 C7 C8 -176.8(3) . . . . ?
C5 C6 C11 C10 178.9(3) . . . . ?
C5 C6 C11 C12 3.0(3) . . . . ?
C5 C13 C14 C2 36.1(4) . . . . ?
C5 C13 C14 C15 -93.3(3) . . . . ?
C6 C5 C13 C12 3.3(3) . . . . ?
C6 C5 C13 C14 -168.3(2) . . . . ?
C6 C7 C8 C9 -1.9(5) . . . . ?
C6 C11 C12 O2 174.8(3) . . . . ?
C6 C11 C12 C13 -1.2(3) . . . . ?
C7 C6 C11 C10 0.8(4) . . . . ?
C7 C6 C11 C12 -175.1(2) . . . . ?
C7 C8 C9 C10 1.4(5) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C9 C10 C11 C6 -1.3(4) . . . . ?
C9 C10 C11 C12 173.4(3) . . . . ?
C10 C11 C12 O2 -0.5(5) . . . . ?
C10 C11 C12 C13 -176.5(3) . . . . ?
C11 C6 C7 C8 0.8(4) . . . . ?
C11 C12 C13 C5 -1.3(3) . . . . ?
C11 C12 C13 C14 171.0(2) . . . . ?
C12 C13 C14 C2 -134.3(3) . . . . ?
C12 C13 C14 C15 96.3(3) . . . . ?
C13 C5 C6 C7 173.7(3) . . . . ?
C13 C5 C6 C11 -4.1(3) . . . . ?
C13 C14 C15 C16 179.2(2) . . . . ?
C13 C14 C15 C20 -4.6(4) . . . . ?
C14 C2 C3 C4 2.0(4) . . . . ?
C14 C15 C16 O5 -0.4(3) . . . . ?
C14 C15 C16 C17 175.0(2) . . . . ?
C14 C15 C20 C19 -177.5(2) . . . . ?
C15 C16 C17 O6 -178.3(2) . . . . ?
C15 C16 C17 C18 3.5(4) . . . . ?
C16 C15 C20 C19 -1.2(4) . . . . ?
C16 C17 C18 O7 177.9(2) . . . . ?
C16 C17 C18 C19 -3.1(4) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C18 C19 C20 C15 1.6(4) . . . . ?
C20 C15 C16 O5 -176.8(2) . . . . ?
C20 C15 C16 C17 -1.4(4) . . . . ?
C21 O3 C1 O4 -2.3(4) . . . . ?
C21 O3 C1 C2 175.5(2) . . . . ?
C23 O5 C16 C15 -121.5(2) . . . . ?
C23 O5 C16 C17 63.0(3) . . . . ?
C24 O6 C17 C16 91.8(3) . . . . ?
C24 O6 C17 C18 -90.1(3) . . . . ?
C25 O7 C18 C17 -176.8(2) . . . . ?
C25 O7 C18 C19 4.4(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1905060293_0m
_database_code_depnum_ccdc_archive 'CCDC 1956081'
loop_
_audit_author_name
_audit_author_address
'zheng jing'
;nanchang university
China
;
_audit_update_record             
;
2019-09-26 deposited with the CCDC.	2020-05-29 downloaded from the CCDC.
;
_audit_creation_date             2019-05-08
_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         'C17 H13 N3 O2'
_chemical_formula_sum            'C17 H13 N3 O2'
_chemical_formula_weight         291.30
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.1711(17)
_cell_length_b                   10.0725(7)
_cell_length_c                   11.4469(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.896(5)
_cell_angle_gamma                90
_cell_volume                     3017.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5264
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      55.07
_cell_measurement_theta_min      4.093
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1621 before and 0.0735 after correction. The Ratio of minimum to maximum transmission is 0.7724. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15336
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.395
_diffrn_reflns_theta_min         2.938
_diffrn_ambient_temperature      169.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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                1900
_reflns_number_total             2904
_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         0.576
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0718
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1018P)²+4.8570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.2159
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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
O1 O 0.54856(10) 0.1179(3) 0.3466(2) 0.0722(8) Uani 1 1 d . . . . .
O2 O 0.51176(10) 0.2886(3) 0.4418(3) 0.0810(9) Uani 1 1 d . . . . .
N1 N 0.40757(12) 0.2329(3) 0.7784(2) 0.0579(8) Uani 1 1 d . . . . .
N2 N 0.31093(13) -0.1163(3) 0.7279(3) 0.0638(8) Uani 1 1 d . . . . .
N3 N 0.30539(11) 0.8128(3) 0.4355(3) 0.0565(8) Uani 1 1 d . . . . .
C1 C 0.33138(11) 0.1432(3) 0.5256(2) 0.0399(7) Uani 1 1 d . . . . .
H1 H 0.300363 0.093358 0.498325 0.048 Uiso 1 1 calc R . . . .
C2 C 0.35771(12) 0.0817(3) 0.6331(3) 0.0407(7) Uani 1 1 d . . . . .
C3 C 0.38011(11) 0.0688(3) 0.5095(2) 0.0400(7) Uani 1 1 d . . . . .
H3 H 0.376668 -0.020580 0.472223 0.048 Uiso 1 1 calc R . . . .
C4 C 0.42831(12) 0.1397(3) 0.4871(3) 0.0422(7) Uani 1 1 d . . . . .
H4 H 0.433878 0.222521 0.524865 0.051 Uiso 1 1 calc R . . . .
C5 C 0.46435(12) 0.0943(3) 0.4172(3) 0.0471(8) Uani 1 1 d . . . . .
H5 H 0.458803 0.011822 0.378766 0.057 Uiso 1 1 calc R . . . .
C6 C 0.51232(14) 0.1652(4) 0.3965(3) 0.0565(9) Uani 1 1 d . . . . .
C7 C 0.55898(18) 0.3655(5) 0.4405(6) 0.118(2) Uani 1 1 d . . . . .
H7A H 0.565128 0.404291 0.518982 0.141 Uiso 1 1 calc R . . . .
H7B H 0.587858 0.305459 0.423498 0.141 Uiso 1 1 calc R . . . .
C8 C 0.55773(19) 0.4665(5) 0.3587(5) 0.1039(18) Uani 1 1 d . . . . .
H8A H 0.555885 0.428187 0.280082 0.156 Uiso 1 1 calc GR . . . .
H8B H 0.588746 0.520418 0.366792 0.156 Uiso 1 1 calc GR . . . .
H8C H 0.527665 0.522363 0.371359 0.156 Uiso 1 1 calc GR . . . .
C9 C 0.38529(12) 0.1662(3) 0.7144(3) 0.0429(7) Uani 1 1 d . . . . .
C10 C 0.33260(13) -0.0304(3) 0.6861(3) 0.0468(8) Uani 1 1 d . . . . .
C11 C 0.32688(11) 0.2902(3) 0.5110(2) 0.0383(7) Uani 1 1 d . . . . .
C12 C 0.34499(12) 0.3502(3) 0.4104(3) 0.0434(7) Uani 1 1 d . . . . .
H12 H 0.361639 0.298119 0.353264 0.052 Uiso 1 1 calc R . . . .
C13 C 0.33898(12) 0.4850(3) 0.3930(3) 0.0442(8) Uani 1 1 d . . . . .
H13 H 0.351797 0.525557 0.324493 0.053 Uiso 1 1 calc R . . . .
C14 C 0.31406(11) 0.5613(3) 0.4760(3) 0.0409(7) Uani 1 1 d . . . . .
C15 C 0.29573(12) 0.5021(3) 0.5771(3) 0.0445(7) Uani 1 1 d . . . . .
H15 H 0.278946 0.554182 0.634097 0.053 Uiso 1 1 calc R . . . .
C16 C 0.30211(11) 0.3678(3) 0.5938(3) 0.0422(7) Uani 1 1 d . . . . .
H16 H 0.289491 0.327404 0.662545 0.051 Uiso 1 1 calc R . . . .
C17 C 0.30847(12) 0.7020(3) 0.4553(3) 0.0454(8) Uani 1 1 d . . . . .


_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 C6 1.212(4) . ?
O2 C6 1.347(5) . ?
O2 C7 1.459(5) . ?
N1 C9 1.147(4) . ?
N2 C10 1.143(4) . ?
N3 C17 1.142(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.532(4) . ?
C1 C3 1.493(4) . ?
C1 C11 1.494(4) . ?
C2 C3 1.546(4) . ?
C2 C9 1.446(4) . ?
C2 C10 1.445(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.475(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.327(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.467(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.382(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 C12 1.391(4) . ?
C11 C16 1.396(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(4) . ?
C14 C15 1.393(4) . ?
C14 C17 1.444(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(4) . ?
C16 H16 0.9500 . ?

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
C6 O2 C7 118.2(4) . . ?
C2 C1 H1 113.6 . . ?
C3 C1 H1 113.6 . . ?
C3 C1 C2 61.44(19) . . ?
C3 C1 C11 123.3(2) . . ?
C11 C1 H1 113.6 . . ?
C11 C1 C2 121.6(2) . . ?
C1 C2 C3 58.02(18) . . ?
C9 C2 C1 119.5(2) . . ?
C9 C2 C3 116.5(3) . . ?
C10 C2 C1 116.8(3) . . ?
C10 C2 C3 120.0(2) . . ?
C10 C2 C9 114.6(3) . . ?
C1 C3 C2 60.53(19) . . ?
C1 C3 H3 115.7 . . ?
C2 C3 H3 115.7 . . ?
C4 C3 C1 120.9(2) . . ?
C4 C3 C2 117.1(2) . . ?
C4 C3 H3 115.7 . . ?
C3 C4 H4 118.1 . . ?
C5 C4 C3 123.8(3) . . ?
C5 C4 H4 118.1 . . ?
C4 C5 H5 118.4 . . ?
C4 C5 C6 123.2(3) . . ?
C6 C5 H5 118.4 . . ?
O1 C6 O2 123.8(3) . . ?
O1 C6 C5 124.3(4) . . ?
O2 C6 C5 111.9(3) . . ?
O2 C7 H7A 109.0 . . ?
O2 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 O2 112.7(4) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C2 179.4(4) . . ?
N2 C10 C2 177.2(4) . . ?
C12 C11 C1 119.7(3) . . ?
C12 C11 C16 119.1(3) . . ?
C16 C11 C1 121.1(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 C17 118.5(3) . . ?
C15 C14 C17 121.4(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15 120.2 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 119.6 . . ?
N3 C17 C14 177.3(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
