#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/07/7150767.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_7150767
loop_
_publ_author_name
'Chantarasriwong, Oraphin'
'Cho, Woo Cheal'
'Batova, Ayse'
'Chavasiri, Warinthorn'
'Moore, Curtis'
'Rheingold, Arnold L.'
'Theodorakis, Emmanuel A.'
_publ_section_title
;
 Evaluation of the pharmacophoric motif of the caged Garcinia xanthones
;
_journal_issue                   23
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4886
_journal_page_last               4894
_journal_paper_doi               10.1039/b913496d
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C20 H26 O5'
_chemical_formula_weight         346.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.650(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9193(4)
_cell_length_b                   12.8300(5)
_cell_length_c                   13.3814(5)
_cell_measurement_reflns_used    6333
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      4.66
_cell_volume                     1805.16(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11208
_diffrn_reflns_theta_full        60.00
_diffrn_reflns_theta_max         68.40
_diffrn_reflns_theta_min         4.66
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.9432
_exptl_absorpt_correction_T_min  0.8087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.00144(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0462P)²+0.5678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                2718
_reflns_number_total             3199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b913496d.txt
_cod_data_source_block           theod32
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7150767
loop_
_symmetry_equiv_pos_as_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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.82804(9) 0.39196(7) 0.79992(7) 0.0225(2) Uani 1 1 d . . .
O2 O 0.96880(8) 0.25013(7) 0.83496(7) 0.0180(2) Uani 1 1 d . . .
O3 O 1.12041(8) 0.10678(7) 0.74979(7) 0.0189(2) Uani 1 1 d . . .
O4 O 1.09519(9) 0.15903(8) 0.53030(7) 0.0254(2) Uani 1 1 d . . .
O5 O 0.76575(10) 0.45611(8) 0.64111(8) 0.0273(2) Uani 1 1 d . . .
C1 C 0.86785(13) 0.29893(11) 0.86433(10) 0.0210(3) Uani 1 1 d . . .
C2 C 0.93728(12) 0.21085(10) 0.73148(10) 0.0160(3) Uani 1 1 d . . .
C3 C 1.06100(12) 0.19783(10) 0.69757(10) 0.0165(3) Uani 1 1 d . . .
C4 C 1.15764(12) 0.28558(10) 0.72196(10) 0.0186(3) Uani 1 1 d . . .
H4A H 1.1774 0.3011 0.7971 0.022 Uiso 1 1 calc R . .
H4B H 1.2371 0.2609 0.7075 0.022 Uiso 1 1 calc R . .
C5 C 1.11765(12) 0.38490(11) 0.66310(10) 0.0193(3) Uani 1 1 d . . .
H5 H 1.1015 0.3807 0.5898 0.023 Uiso 1 1 calc R . .
C6 C 1.10207(12) 0.47824(11) 0.70145(11) 0.0207(3) Uani 1 1 d . . .
C7 C 1.11788(14) 0.50154(12) 0.81396(11) 0.0264(3) Uani 1 1 d . . .
H7A H 1.1305 0.4363 0.8535 0.040 Uiso 1 1 calc R . .
H7B H 1.0415 0.5368 0.8221 0.040 Uiso 1 1 calc R . .
H7C H 1.1920 0.5468 0.8398 0.040 Uiso 1 1 calc R . .
C8 C 0.92350(15) 0.33902(12) 0.97288(11) 0.0290(3) Uani 1 1 d . . .
H8A H 0.9964 0.3841 0.9742 0.043 Uiso 1 1 calc R . .
H8B H 0.9515 0.2801 1.0201 0.043 Uiso 1 1 calc R . .
H8C H 0.8589 0.3789 0.9950 0.043 Uiso 1 1 calc R . .
C9 C 0.81026(12) 0.38366(11) 0.69645(11) 0.0199(3) Uani 1 1 d . . .
C10 C 0.84964(12) 0.28437(10) 0.65835(10) 0.0175(3) Uani 1 1 d . . .
C11 C 0.81936(12) 0.25831(11) 0.55836(10) 0.0193(3) Uani 1 1 d . . .
H11 H 0.7671 0.3003 0.5052 0.023 Uiso 1 1 calc R . .
C12 C 0.87534(12) 0.15674(11) 0.53731(10) 0.0202(3) Uani 1 1 d . . .
H12 H 0.8501 0.1382 0.4619 0.024 Uiso 1 1 calc R . .
C13 C 1.01879(13) 0.17102(10) 0.57996(10) 0.0185(3) Uani 1 1 d . . .
C14 C 1.06717(15) 0.57164(11) 0.63161(12) 0.0291(3) Uani 1 1 d . . .
H14A H 0.9803 0.5936 0.6288 0.044 Uiso 1 1 calc R . .
H14B H 1.0721 0.5534 0.5617 0.044 Uiso 1 1 calc R . .
H14C H 1.1263 0.6288 0.6589 0.044 Uiso 1 1 calc R . .
C15 C 0.89568(12) 0.09430(10) 0.72145(10) 0.0167(3) Uani 1 1 d . . .
H15 H 0.8344 0.0801 0.7635 0.020 Uiso 1 1 calc R . .
C16 C 1.02335(12) 0.03662(10) 0.76838(10) 0.0182(3) Uani 1 1 d . . .
C17 C 1.05043(13) 0.02229(12) 0.88506(11) 0.0241(3) Uani 1 1 d . . .
H17A H 1.0410 0.0893 0.9174 0.036 Uiso 1 1 calc R . .
H17B H 1.1374 -0.0035 0.9131 0.036 Uiso 1 1 calc R . .
H17C H 0.9903 -0.0281 0.8999 0.036 Uiso 1 1 calc R . .
C18 C 1.03773(14) -0.06750(11) 0.71874(12) 0.0267(3) Uani 1 1 d . . .
H18A H 1.1204 -0.0981 0.7538 0.040 Uiso 1 1 calc R . .
H18B H 1.0323 -0.0570 0.6451 0.040 Uiso 1 1 calc R . .
H18C H 0.9697 -0.1146 0.7253 0.040 Uiso 1 1 calc R . .
C19 C 0.83255(12) 0.07304(11) 0.60526(10) 0.0197(3) Uani 1 1 d . . .
H19A H 0.7389 0.0749 0.5919 0.024 Uiso 1 1 calc R . .
H19B H 0.8570 0.0029 0.5866 0.024 Uiso 1 1 calc R . .
C20 C 0.75214(14) 0.23087(11) 0.85612(11) 0.0244(3) Uani 1 1 d . . .
H20A H 0.7781 0.1661 0.8949 0.037 Uiso 1 1 calc R . .
H20B H 0.7123 0.2145 0.7830 0.037 Uiso 1 1 calc R . .
H20C H 0.6912 0.2680 0.8851 0.037 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C9 O1 C1 118.43(10) . . ?
C1 O2 C2 115.15(10) . . ?
C3 O3 C16 109.47(9) . . ?
O2 C1 O1 109.07(10) . . ?
O2 C1 C8 106.12(11) . . ?
O1 C1 C8 105.50(11) . . ?
O2 C1 C20 114.99(11) . . ?
O1 C1 C20 108.48(11) . . ?
C8 C1 C20 112.24(12) . . ?
O2 C2 C10 110.79(10) . . ?
O2 C2 C3 108.80(10) . . ?
C10 C2 C3 109.28(10) . . ?
O2 C2 C15 114.29(10) . . ?
C10 C2 C15 115.26(11) . . ?
C3 C2 C15 97.39(10) . . ?
O3 C3 C4 107.74(10) . . ?
O3 C3 C2 105.24(10) . . ?
C4 C3 C2 117.97(11) . . ?
O3 C3 C13 106.65(10) . . ?
C4 C3 C13 112.41(10) . . ?
C2 C3 C13 106.09(10) . . ?
C5 C4 C3 115.49(11) . . ?
C6 C5 C4 127.67(13) . . ?
C5 C6 C7 125.06(13) . . ?
C5 C6 C14 120.94(13) . . ?
C7 C6 C14 113.99(12) . . ?
O5 C9 O1 119.46(13) . . ?
O5 C9 C10 123.98(13) . . ?
O1 C9 C10 116.56(12) . . ?
C11 C10 C9 123.13(13) . . ?
C11 C10 C2 116.01(12) . . ?
C9 C10 C2 120.65(12) . . ?
C10 C11 C12 113.84(12) . . ?
C11 C12 C13 104.77(11) . . ?
C11 C12 C19 106.74(11) . . ?
C13 C12 C19 107.67(10) . . ?
O4 C13 C12 124.75(12) . . ?
O4 C13 C3 121.66(12) . . ?
C12 C13 C3 113.53(10) . . ?
C19 C15 C16 115.52(10) . . ?
C19 C15 C2 107.25(10) . . ?
C16 C15 C2 102.32(10) . . ?
O3 C16 C18 107.57(11) . . ?
O3 C16 C17 107.48(10) . . ?
C18 C16 C17 109.18(12) . . ?
O3 C16 C15 104.51(10) . . ?
C18 C16 C15 115.44(11) . . ?
C17 C16 C15 112.19(11) . . ?
C15 C19 C12 110.05(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
O1 C9 1.3495(17) . ?
O1 C1 1.4678(16) . ?
O2 C1 1.4126(15) . ?
O2 C2 1.4257(15) . ?
O3 C3 1.4245(15) . ?
O3 C16 1.4621(15) . ?
O4 C13 1.2085(15) . ?
O5 C9 1.2061(17) . ?
C1 C8 1.5059(19) . ?
C1 C20 1.515(2) . ?
C2 C10 1.5027(18) . ?
C2 C3 1.5458(17) . ?
C2 C15 1.5580(18) . ?
C3 C4 1.5170(18) . ?
C3 C13 1.5543(17) . ?
C4 C5 1.4998(18) . ?
C5 C6 1.332(2) . ?
C6 C7 1.4985(19) . ?
C6 C14 1.5041(19) . ?
C9 C10 1.4784(18) . ?
C10 C11 1.3315(19) . ?
C11 C12 1.4980(19) . ?
C12 C13 1.5266(18) . ?
C12 C19 1.5580(18) . ?
C15 C19 1.5454(17) . ?
C15 C16 1.5535(18) . ?
C16 C18 1.5187(18) . ?
C16 C17 1.5198(19) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102168233
