#------------------------------------------------------------------------------
#$Date: 2021-06-26 03:00:31 +0300 (Sat, 26 Jun 2021) $
#$Revision: 266699 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/37/1563709.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1563709
loop_
_publ_author_name
'Hu, Yun-Wei'
'Liu, Ying'
'Guo, Er-Yan'
'Wang, Yu-Ying'
'Xu, Wan-Qi'
'Gao, Yan'
'Jiang, Xue-Yang'
'Feng, Feng'
'Xu, Jian'
'Liu, Wen-Yuan'
_publ_section_title
;
 Naphtho-γ-pyrone Dimers from an Endozoic Aspergillus niger and
 the Effects of Coisolated Monomers in Combination with Cisplatin on a
 Cisplatin-Resistant A549 Cell Line.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.0c01262
_journal_year                    2021
_chemical_formula_moiety         'C20 H12 O8, 2(H2 O)'
_chemical_formula_sum            'C20 H16 O10'
_chemical_formula_weight         416.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                101.320(15)
_cell_angle_beta                 93.023(16)
_cell_angle_gamma                99.194(15)
_cell_formula_units_Z            2
_cell_length_a                   7.160(3)
_cell_length_b                   9.102(4)
_cell_length_c                   13.073(6)
_cell_measurement_reflns_used    1141
_cell_measurement_temperature    150
_cell_measurement_theta_max      23.733
_cell_measurement_theta_min      2.317
_cell_volume                     821.5(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_unetI/netI     0.1366
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7396
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.055
_diffrn_reflns_theta_max         25.055
_diffrn_reflns_theta_min         2.317
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.0912
_exptl_absorpt_correction_T_min  0.0656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0762 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.7193. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.1851
_refine_ls_R_factor_gt           0.1235
_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)+(0.1412P)²+30.3850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3286
_refine_ls_wR_factor_ref         0.3766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1715
_reflns_number_total             2857
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np0c01262_si_001.cif
_cod_data_source_block           n_0m
_cod_database_code               1563709
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.993
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.872(4)
 0.128(4)
2. 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, All O(H,H) groups
3.a Free rotating group:
 O8(H8C,H8D), O10(H10A,H10B)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C1(H1), C3(H3A), C17(H17), C19(H19)
3.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O7(H7), O3(H3), O9(H9), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O4 O 0.5838(11) 0.1498(8) 0.6004(6) 0.0189(18) Uani 1 1 d . . . . .
O5 O 0.4249(11) 0.1674(9) 0.7492(6) 0.0200(18) Uani 1 1 d . . . . .
H5 H 0.337436 0.191713 0.714032 0.030 Uiso 1 1 calc GR . . . .
O6 O 0.6832(12) 0.3587(9) 0.3037(7) 0.0233(19) Uani 1 1 d . . . . .
O7 O 0.8080(13) 0.6385(9) 0.3214(7) 0.026(2) Uani 1 1 d . . . . .
H7 H 0.771058 0.548458 0.288631 0.039 Uiso 1 1 calc GR . . . .
O3 O 0.6448(12) 0.8293(9) 0.9946(7) 0.0232(19) Uani 1 1 d . . . . .
H3 H 0.601283 0.859955 0.943197 0.035 Uiso 1 1 calc GR . . . .
O1 O 0.8295(12) 0.1651(9) 0.9488(7) 0.026(2) Uani 1 1 d . . . . .
O9 O 1.0219(12) 0.9315(9) 0.6549(7) 0.026(2) Uani 1 1 d . . . . .
H9 H 1.035222 0.926387 0.718298 0.040 Uiso 1 1 calc GR . . . .
O2 O 0.8253(13) 0.4041(10) 1.0919(7) 0.027(2) Uani 1 1 d . . . . .
H2 H 0.833727 0.312808 1.068357 0.040 Uiso 1 1 calc GR . . . .
O8 O 0.5866(13) 0.1027(10) 0.1526(7) 0.030(2) Uani 1 1 d . . . . .
H8C H 0.605162 0.162686 0.214207 0.046 Uiso 1 1 d G . . . .
H8D H 0.598018 0.010927 0.158595 0.046 Uiso 1 1 d G . . . .
O10 O 1.0223(13) 0.9355(10) 0.8590(7) 0.031(2) Uani 1 1 d . . . . .
H10A H 1.123688 0.954280 0.902444 0.047 Uiso 1 1 d G . . . .
H10B H 0.935283 0.981934 0.888089 0.047 Uiso 1 1 d G . . . .
C14 C 0.6844(14) 0.3720(13) 0.4019(10) 0.018(2) Uani 1 1 d . . . . .
C18 C 0.9233(14) 0.7933(12) 0.5970(9) 0.014(2) Uani 1 1 d . . . . .
C12 C 0.6317(15) 0.2612(12) 0.5498(10) 0.018(3) Uani 1 1 d . . . . .
C9 C 0.6001(16) 0.2114(12) 0.7100(9) 0.018(2) Uani 1 1 d . . . . .
C13 C 0.6231(16) 0.2416(13) 0.4452(9) 0.019(2) Uani 1 1 d . . . . .
H13 H 0.578022 0.144555 0.401421 0.022 Uiso 1 1 calc R . . . .
C16 C 0.7628(15) 0.5390(13) 0.5792(9) 0.018(2) Uani 1 1 d . . . . .
C4 C 0.7734(15) 0.4688(14) 1.0116(10) 0.023(3) Uani 1 1 d . . . . .
C11 C 0.6851(16) 0.4059(13) 0.6231(10) 0.021(3) Uani 1 1 d . . . . .
C15 C 0.7528(16) 0.5202(13) 0.4697(10) 0.020(3) Uani 1 1 d . . . . .
C6 C 0.6935(15) 0.4680(12) 0.8302(9) 0.016(2) Uani 1 1 d . . . . .
C20 C 0.8169(16) 0.6426(13) 0.4245(9) 0.020(3) Uani 1 1 d . . . . .
C1 C 0.6585(16) 0.6152(12) 0.8566(10) 0.020(2) Uani 1 1 d . . . . .
H1 H 0.621741 0.666001 0.803893 0.023 Uiso 1 1 calc R . . . .
C5 C 0.7472(16) 0.3875(13) 0.9068(10) 0.020(3) Uani 1 1 d . . . . .
C8 C 0.7500(16) 0.1502(12) 0.7676(10) 0.020(3) Uani 1 1 d . . . . .
H8A H 0.709616 0.039667 0.762837 0.024 Uiso 1 1 calc R . . . .
H8B H 0.871314 0.165675 0.734930 0.024 Uiso 1 1 calc R . . . .
C10 C 0.6644(16) 0.3799(13) 0.7197(10) 0.022(3) Uani 1 1 d . . . . .
C3 C 0.7408(17) 0.6162(13) 1.0393(10) 0.025(3) Uani 1 1 d . . . . .
H3A H 0.760886 0.668255 1.110451 0.030 Uiso 1 1 calc R . . . .
C17 C 0.8520(16) 0.6789(13) 0.6440(10) 0.023(3) Uani 1 1 d . . . . .
H17 H 0.861620 0.692130 0.718078 0.028 Uiso 1 1 calc R . . . .
C19 C 0.9057(16) 0.7858(13) 0.4908(10) 0.024(3) Uani 1 1 d . . . . .
H19 H 0.950318 0.871649 0.461991 0.029 Uiso 1 1 calc R . . . .
C2 C 0.6784(17) 0.6884(14) 0.9628(10) 0.026(3) Uani 1 1 d . . . . .
C7 C 0.7779(16) 0.2321(14) 0.8814(10) 0.025(3) Uani 1 1 d . . . . .
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'
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
C12 O4 C9 109.2(8) . . ?
C9 O5 H5 109.5 . . ?
C20 O7 H7 109.5 . . ?
C2 O3 H3 109.5 . . ?
C18 O9 H9 109.5 . . ?
C4 O2 H2 109.5 . . ?
H8C O8 H8D 109.5 . . ?
H10A O10 H10B 109.5 . . ?
O6 C14 C13 120.0(10) . . ?
O6 C14 C15 119.2(10) . . ?
C13 C14 C15 120.8(11) . . ?
C17 C18 O9 121.4(10) . . ?
C17 C18 C19 124.4(11) . . ?
C19 C18 O9 114.2(10) . . ?
O4 C12 C13 123.9(10) . . ?
O4 C12 C11 110.6(10) . . ?
C13 C12 C11 125.4(11) . . ?
O4 C9 C8 111.6(9) . . ?
O4 C9 C10 104.7(9) . . ?
O5 C9 O4 108.3(9) . . ?
O5 C9 C8 107.6(9) . . ?
O5 C9 C10 116.2(9) . . ?
C10 C9 C8 108.5(9) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 C14 117.6(11) . . ?
C12 C13 H13 121.2 . . ?
C15 C16 C11 117.6(10) . . ?
C15 C16 C17 120.4(11) . . ?
C17 C16 C11 122.0(11) . . ?
O2 C4 C5 121.8(10) . . ?
O2 C4 C3 116.1(12) . . ?
C3 C4 C5 122.0(11) . . ?
C12 C11 C16 116.9(11) . . ?
C10 C11 C12 107.5(11) . . ?
C10 C11 C16 135.3(11) . . ?
C16 C15 C14 121.1(10) . . ?
C20 C15 C14 118.9(11) . . ?
C20 C15 C16 120.0(11) . . ?
C1 C6 C5 122.3(11) . . ?
C1 C6 C10 121.8(11) . . ?
C5 C6 C10 115.8(10) . . ?
O7 C20 C15 124.8(11) . . ?
O7 C20 C19 115.8(10) . . ?
C15 C20 C19 119.4(11) . . ?
C6 C1 H1 120.6 . . ?
C6 C1 C2 118.8(11) . . ?
C2 C1 H1 120.6 . . ?
C4 C5 C6 116.4(10) . . ?
C4 C5 C7 120.4(11) . . ?
C6 C5 C7 123.2(11) . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C7 C8 C9 109.6(9) . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
C11 C10 C9 107.9(10) . . ?
C11 C10 C6 138.3(11) . . ?
C6 C10 C9 113.7(10) . . ?
C4 C3 H3A 120.0 . . ?
C4 C3 C2 119.9(12) . . ?
C2 C3 H3A 120.0 . . ?
C18 C17 C16 118.0(11) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C18 C19 C20 117.6(10) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 H19 121.2 . . ?
O3 C2 C1 122.4(11) . . ?
O3 C2 C3 117.2(11) . . ?
C3 C2 C1 120.4(11) . . ?
O1 C7 C5 122.4(12) . . ?
O1 C7 C8 119.2(11) . . ?
C5 C7 C8 118.4(11) . . ?
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
O4 C12 1.326(14) . ?
O4 C9 1.424(14) . ?
O5 H5 0.8400 . ?
O5 C9 1.409(14) . ?
O6 C14 1.265(14) . ?
O7 H7 0.8400 . ?
O7 C20 1.338(15) . ?
O3 H3 0.8400 . ?
O3 C2 1.332(15) . ?
O1 C7 1.238(15) . ?
O9 H9 0.8400 . ?
O9 C18 1.393(13) . ?
O2 H2 0.8400 . ?
O2 C4 1.364(15) . ?
O8 H8C 0.8698 . ?
O8 H8D 0.8700 . ?
O10 H10A 0.8698 . ?
O10 H10B 0.8700 . ?
C14 C13 1.430(16) . ?
C14 C15 1.455(16) . ?
C18 C17 1.355(16) . ?
C18 C19 1.375(17) . ?
C12 C13 1.341(17) . ?
C12 C11 1.450(16) . ?
C9 C8 1.516(15) . ?
C9 C10 1.507(15) . ?
C13 H13 0.9500 . ?
C16 C11 1.482(17) . ?
C16 C15 1.405(17) . ?
C16 C17 1.416(17) . ?
C4 C5 1.410(18) . ?
C4 C3 1.379(17) . ?
C11 C10 1.341(18) . ?
C15 C20 1.387(16) . ?
C6 C1 1.383(16) . ?
C6 C5 1.424(16) . ?
C6 C10 1.495(17) . ?
C20 C19 1.445(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.406(17) . ?
C5 C7 1.442(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.515(17) . ?
C3 H3A 0.9500 . ?
C3 C2 1.391(18) . ?
C17 H17 0.9500 . ?
C19 H19 0.9500 . ?
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
_geom_hbond_publ_flag
O5 H5 O7 0.84 2.11 2.858(12) 149.0 2_666 yes
O7 H7 O6 0.84 1.79 2.521(11) 143.8 . yes
O3 H3 O8 0.84 1.91 2.700(13) 157.4 2_666 yes
O9 H9 O10 0.84 1.83 2.661(13) 168.2 . yes
O2 H2 O1 0.84 1.85 2.581(12) 145.2 . yes
O8 H8C O6 0.87 1.91 2.710(12) 151.7 . yes
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.872(4)
2 0.128(4)
