# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# 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_KAD-1
_database_code_depnum_ccdc_archive 'CCDC 2113649'
loop_
_audit_author_name
_audit_author_address
'Xueyan Liu '
;School of pharmacy, Fujian Medical University
China
;
_audit_update_record             
;
2021-10-04 deposited with the CCDC.	2022-12-07 downloaded from the CCDC.
;
_audit_creation_date             2021-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C12 H10 O8'
_chemical_formula_sum            'C12 H10 O8'
_chemical_formula_weight         282.21
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
C 0.01370 0.00670 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.03890 0.02410 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   3.8200(4)
_cell_length_b                   17.5109(17)
_cell_length_c                   8.4469(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.527(8)
_cell_angle_gamma                90
_cell_volume                     557.23(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2041
_cell_measurement_theta_min      4.3950
_cell_measurement_theta_max      60.4450
_cell_measurement_temperature    293(2)
_exptl_absorpt_coefficient_mu    0.803
_exptl_crystal_description       Prism
_exptl_crystal_density_diffrn    1.6818
_exptl_crystal_F_000             292.9220
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3560
_diffrn_reflns_theta_full        60.4977
_diffrn_reflns_theta_max         60.50
_diffrn_reflns_theta_min         4.39
_diffrn_measured_fraction_theta_full 0.9747
_diffrn_measured_fraction_theta_max 0.9747
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.3405
_diffrn_ambient_temperature      293(2)
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              -3
_reflns_number_gt                1062
_reflns_number_total             1235
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.2321
_refine_diff_density_min         -0.1968
_refine_diff_density_rms         0.0462
_refine_ls_d_res_high            0.7701
_refine_ls_d_res_low             8.7555
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0550
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    9
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.0550
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.1330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1030
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.c Idealised tetrahedral OH refined as rotating group:
 O8(H8), O9(H9)
;
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_refinement_flags_posn
O6 O 0.0851(3) 0.45228(5) 0.68738(11) 0.0301(3) Uani 1.000000 .
O8 O 0.3803(3) 0.33344(6) 1.02709(11) 0.0349(3) Uani 1.000000 .
H8 H 0.271(3) 0.2933(2) 1.0087(17) 0.0523(4) Uiso 1.000000 GR
O10 O 0.4957(3) 0.29273(6) 0.42824(12) 0.0400(3) Uani 1.000000 .
O9 O 0.2298(4) 0.41855(6) 0.28196(12) 0.0463(3) Uani 1.000000 .
H9 H 0.310(6) 0.3797(5) 0.2472(6) 0.0695(5) Uiso 1.000000 GR
C5 C 0.0801(4) 0.46355(7) 0.52658(16) 0.0265(3) Uani 1.000000 .
C1 C 0.2252(4) 0.38858(8) 0.76043(16) 0.0272(3) Uani 1.000000 .
C2 C 0.3641(4) 0.33264(8) 0.68206(16) 0.0301(3) Uani 1.000000 .
H2 H 0.4566(4) 0.28915(8) 0.73688(16) 0.0362(4) Uiso 1.000000 R
C4 C 0.2192(4) 0.40986(8) 0.43870(16) 0.0290(3) Uani 1.000000 .
C3 C 0.3698(4) 0.33998(8) 0.51431(16) 0.0289(3) Uani 1.000000 .
C7 C 0.1982(4) 0.39197(8) 0.93587(16) 0.0328(3) Uani 1.000000 .
H7a H -0.0502(4) 0.38966(8) 0.94702(16) 0.0393(4) Uiso 1.000000 R
H7b H 0.2909(4) 0.44067(8) 0.97868(16) 0.0393(4) Uiso 1.000000 R


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
O6 C5 1.3695(15) . ?
O6 C1 1.3424(16) . ?
O8 C7 1.3967(17) . ?
O10 C3 1.2491(16) . ?
O9 C4 1.3399(16) . ?
C5 C5 1.454(3) 3_566 ?
C5 C4 1.3593(18) . ?
C1 C2 1.3401(18) . ?
C1 C7 1.5036(18) . ?
C2 C3 1.4265(18) . ?
C4 C3 1.4542(19) . ?

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
C1 O6 C5 120.98(10) . . ?
C5 C5 O6 111.65(14) 3_566 . ?
C4 C5 O6 119.96(12) . . ?
C2 C1 O6 122.73(12) . . ?
C7 C1 O6 109.46(11) . . ?
C7 C1 C2 127.81(12) . . ?
C3 C2 C1 119.81(12) . . ?
C5 C4 O9 122.65(12) . . ?
C3 C4 O9 117.07(11) . . ?
C3 C4 C5 120.27(12) . . ?
C2 C3 O10 126.09(13) . . ?
C4 C3 O10 117.66(12) . . ?
C4 C3 C2 116.24(11) . . ?
C1 C7 O8 113.93(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_colour            white
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        'developing cottonseed when aflatoxin invades'
_exptl_crystal_preparation       Luminescent
