#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:12:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180293 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/07/7150768.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_7150768
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
_chemical_name_systematic
;
?
;
_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                 92.4170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0045(2)
_cell_length_b                   13.2751(4)
_cell_length_c                   16.4708(5)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.33
_cell_volume                     1748.64(9)
_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 0.973
_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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13879
_diffrn_reflns_theta_full        60.00
_diffrn_reflns_theta_max         68.15
_diffrn_reflns_theta_min         4.28
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0044(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0315
_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)+(0.0282P)²+0.9146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                3004
_reflns_number_total             3087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b913496d.txt
_cod_data_source_block           theod35
_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               7150768
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 1.27011(11) 0.42467(6) -0.03099(5) 0.0211(2) Uani 1 1 d . . .
O2 O 1.15203(10) 0.57579(6) -0.03231(5) 0.01713(19) Uani 1 1 d . . .
O3 O 1.10517(9) 0.67070(6) 0.08594(5) 0.01532(19) Uani 1 1 d . . .
O4 O 1.35035(10) 0.59241(6) 0.33077(5) 0.01598(19) Uani 1 1 d . . .
O5 O 1.37053(10) 0.72997(6) 0.19299(5) 0.0195(2) Uani 1 1 d . . .
C1 C 1.22977(14) 0.49788(9) 0.00679(7) 0.0157(2) Uani 1 1 d . . .
C2 C 1.25054(13) 0.50884(8) 0.09584(7) 0.0146(2) Uani 1 1 d . . .
C3 C 1.18357(14) 0.59978(8) 0.13873(7) 0.0139(2) Uani 1 1 d . . .
C4 C 1.32828(14) 0.64272(8) 0.19250(7) 0.0140(2) Uani 1 1 d . . .
C5 C 1.40336(14) 0.56321(8) 0.25230(7) 0.0142(2) Uani 1 1 d . . .
C6 C 1.59408(14) 0.56093(9) 0.25406(7) 0.0168(2) Uani 1 1 d . . .
H6A H 1.6321 0.5379 0.2007 0.020 Uiso 1 1 calc R . .
H6B H 1.6382 0.6297 0.2640 0.020 Uiso 1 1 calc R . .
C7 C 1.66119(14) 0.49132(9) 0.31967(7) 0.0175(3) Uani 1 1 d . . .
H7 H 1.6645 0.5171 0.3735 0.021 Uiso 1 1 calc R . .
C8 C 1.71640(14) 0.39760(9) 0.31060(7) 0.0170(2) Uani 1 1 d . . .
C9 C 1.76710(16) 0.33284(10) 0.38238(8) 0.0237(3) Uani 1 1 d . . .
H9A H 1.7585 0.3719 0.4325 0.036 Uiso 1 1 calc R . .
H9B H 1.8828 0.3102 0.3774 0.036 Uiso 1 1 calc R . .
H9C H 1.6931 0.2741 0.3841 0.036 Uiso 1 1 calc R . .
C10 C 1.16477(15) 0.67537(9) 0.00654(7) 0.0164(2) Uani 1 1 d . . .
C11 C 1.04332(16) 0.74199(9) -0.04100(8) 0.0209(3) Uani 1 1 d . . .
H11A H 1.0475 0.8102 -0.0183 0.031 Uiso 1 1 calc R . .
H11B H 0.9299 0.7150 -0.0375 0.031 Uiso 1 1 calc R . .
H11C H 1.0736 0.7440 -0.0980 0.031 Uiso 1 1 calc R . .
C12 C 1.05231(14) 0.56026(9) 0.19772(7) 0.0147(2) Uani 1 1 d . . .
H12A H 0.9968 0.6179 0.2236 0.018 Uiso 1 1 calc R . .
H12B H 0.9658 0.5208 0.1670 0.018 Uiso 1 1 calc R . .
C13 C 1.13827(14) 0.49322(8) 0.26378(7) 0.0147(2) Uani 1 1 d . . .
H13 H 1.0690 0.4322 0.2740 0.018 Uiso 1 1 calc R . .
C14 C 1.31395(14) 0.46224(8) 0.23417(7) 0.0143(2) Uani 1 1 d . . .
H14 H 1.3639 0.4064 0.2679 0.017 Uiso 1 1 calc R . .
C15 C 1.31339(14) 0.43777(8) 0.14565(7) 0.0149(2) Uani 1 1 d . . .
H15 H 1.3550 0.3757 0.1261 0.018 Uiso 1 1 calc R . .
C16 C 1.18870(14) 0.54656(9) 0.34482(7) 0.0157(2) Uani 1 1 d . . .
C17 C 1.21365(16) 0.46999(9) 0.41327(8) 0.0221(3) Uani 1 1 d . . .
H17A H 1.2763 0.5012 0.4590 0.033 Uiso 1 1 calc R . .
H17B H 1.2762 0.4120 0.3937 0.033 Uiso 1 1 calc R . .
H17C H 1.1045 0.4475 0.4310 0.033 Uiso 1 1 calc R . .
C18 C 1.07399(15) 0.63043(9) 0.37141(7) 0.0203(3) Uani 1 1 d . . .
H18A H 1.0741 0.6852 0.3315 0.030 Uiso 1 1 calc R . .
H18B H 1.1138 0.6559 0.4246 0.030 Uiso 1 1 calc R . .
H18C H 0.9601 0.6042 0.3752 0.030 Uiso 1 1 calc R . .
C19 C 1.73116(15) 0.34616(9) 0.23004(7) 0.0206(3) Uani 1 1 d . . .
H19A H 1.7045 0.3941 0.1862 0.031 Uiso 1 1 calc R . .
H19B H 1.6530 0.2894 0.2262 0.031 Uiso 1 1 calc R . .
H19C H 1.8456 0.3214 0.2252 0.031 Uiso 1 1 calc R . .
C20 C 1.34527(15) 0.70899(9) 0.00280(7) 0.0191(3) Uani 1 1 d . . .
H20A H 1.4181 0.6599 0.0313 0.029 Uiso 1 1 calc R . .
H20B H 1.3588 0.7751 0.0288 0.029 Uiso 1 1 calc R . .
H20C H 1.3757 0.7137 -0.0541 0.029 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
C1 O2 C10 117.21(9) . . ?
C3 O3 C10 116.18(8) . . ?
C5 O4 C16 109.24(8) . . ?
O1 C1 O2 119.83(11) . . ?
O1 C1 C2 124.82(11) . . ?
O2 C1 C2 115.28(10) . . ?
C15 C2 C1 124.39(10) . . ?
C15 C2 C3 114.21(10) . . ?
C1 C2 C3 121.11(10) . . ?
O3 C3 C2 113.77(9) . . ?
O3 C3 C4 114.35(9) . . ?
C2 C3 C4 107.00(9) . . ?
O3 C3 C12 108.43(9) . . ?
C2 C3 C12 106.61(9) . . ?
C4 C3 C12 106.14(9) . . ?
O5 C4 C3 124.32(10) . . ?
O5 C4 C5 123.31(10) . . ?
C3 C4 C5 112.13(9) . . ?
O4 C5 C6 108.84(9) . . ?
O4 C5 C14 104.91(9) . . ?
C6 C5 C14 116.23(9) . . ?
O4 C5 C4 105.55(9) . . ?
C6 C5 C4 112.76(9) . . ?
C14 C5 C4 107.74(9) . . ?
C7 C6 C5 110.64(9) . . ?
C8 C7 C6 127.17(11) . . ?
C7 C8 C19 124.28(11) . . ?
C7 C8 C9 121.75(11) . . ?
C19 C8 C9 113.97(10) . . ?
O3 C10 O2 110.09(9) . . ?
O3 C10 C11 105.72(9) . . ?
O2 C10 C11 105.65(9) . . ?
O3 C10 C20 114.23(9) . . ?
O2 C10 C20 107.20(9) . . ?
C11 C10 C20 113.62(10) . . ?
C13 C12 C3 110.03(9) . . ?
C12 C13 C16 115.82(9) . . ?
C12 C13 C14 108.16(9) . . ?
C16 C13 C14 100.60(9) . . ?
C15 C14 C5 111.11(9) . . ?
C15 C14 C13 113.34(9) . . ?
C5 C14 C13 97.31(9) . . ?
C2 C15 C14 115.58(10) . . ?
O4 C16 C18 106.93(9) . . ?
O4 C16 C17 107.84(9) . . ?
C18 C16 C17 109.72(10) . . ?
O4 C16 C13 104.76(9) . . ?
C18 C16 C13 116.39(9) . . ?
C17 C16 C13 110.70(9) . . ?
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 C1 1.2054(14) . ?
O2 C1 1.3557(14) . ?
O2 C10 1.4704(13) . ?
O3 C3 1.4106(13) . ?
O3 C10 1.4122(14) . ?
O4 C5 1.4307(14) . ?
O4 C16 1.4572(13) . ?
O5 C4 1.2066(14) . ?
C1 C2 1.4763(16) . ?
C2 C15 1.3347(16) . ?
C2 C3 1.5086(15) . ?
C3 C4 1.5377(15) . ?
C3 C12 1.5522(15) . ?
C4 C5 1.5477(15) . ?
C5 C6 1.5260(15) . ?
C5 C14 1.5427(15) . ?
C6 C7 1.5037(16) . ?
C7 C8 1.3308(17) . ?
C8 C19 1.5014(17) . ?
C8 C9 1.5037(17) . ?
C10 C11 1.5087(16) . ?
C10 C20 1.5159(16) . ?
C12 C13 1.5448(15) . ?
C13 C16 1.5495(16) . ?
C13 C14 1.5627(15) . ?
C14 C15 1.4936(16) . ?
C16 C18 1.5193(16) . ?
C16 C17 1.5249(16) . ?
