#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/88/2228808.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2228808
loop_
_publ_author_name
'Loh, Wan-Sin'
'Fun, Hoong-Kun'
'Reddy, B. Palakshi'
'Vijayakumar, V.'
'Sarveswari, S.'
_publ_section_title
;
 4a-Hydroxy-9-(2-methoxyphenyl)-4,4a,5,6,7,8,9,9a-octahydro-3H-xanthene-1,8(2H)-dione
;
_journal_coeditor_code           LH5179
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o35
_journal_page_last               o36
_journal_paper_doi               10.1107/S1600536810050191
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H22 O5'
_chemical_formula_moiety         'C20 H22 O5'
_chemical_formula_sum            'C20 H22 O5'
_chemical_formula_weight         342.38
_chemical_name_systematic
;
4a-Hydroxy-9-(2-methoxyphenyl)-4,4a,5,6,7,8,9,9a-octahydro-3H-
xanthene-1,8(2H)-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.2850(10)
_cell_angle_beta                 101.2510(10)
_cell_angle_gamma                101.1290(10)
_cell_formula_units_Z            2
_cell_length_a                   7.10600(10)
_cell_length_b                   7.88970(10)
_cell_length_c                   15.1001(2)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      37.19
_cell_measurement_theta_min      2.64
_cell_volume                     813.102(19)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21213
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.3385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                4132
_reflns_number_total             4715
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5179.cif
_cod_data_source_block           I
_cod_database_code               2228808
_cod_database_fobs_code          2228808
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.99328(11) 0.05712(9) 0.14023(5) 0.01184(15) Uani d . 1 . .
O O2 0.70333(12) 0.35590(10) 0.19525(6) 0.01849(17) Uani d . 1 . .
O O3 0.34225(11) -0.15228(10) 0.17249(5) 0.01475(16) Uani d . 1 . .
O O4 0.74431(12) 0.15152(9) 0.43898(5) 0.01407(16) Uani d . 1 . .
O O5 1.11520(11) -0.03057(9) 0.28104(5) 0.01311(15) Uani d . 1 . .
C C1 1.06767(15) 0.11229(12) 0.23546(6) 0.01072(18) Uani d . 1 . .
C C2 1.24660(15) 0.25412(13) 0.23649(7) 0.01350(19) Uani d . 1 . .
H H2A 1.3340 0.2104 0.2039 0.016 Uiso calc R 1 . .
H H2B 1.3158 0.2835 0.2986 0.016 Uiso calc R 1 . .
C C3 1.19583(16) 0.41749(13) 0.19413(7) 0.0163(2) Uani d . 1 . .
H H3A 1.1438 0.3927 0.1298 0.020 Uiso calc R 1 . .
H H3B 1.3137 0.5066 0.2015 0.020 Uiso calc R 1 . .
C C4 1.04414(17) 0.48393(13) 0.23831(8) 0.0172(2) Uani d . 1 . .
H H4A 1.1005 0.5208 0.3012 0.021 Uiso calc R 1 . .
H H4B 1.0064 0.5825 0.2075 0.021 Uiso calc R 1 . .
C C5 0.86650(16) 0.34065(13) 0.23232(7) 0.01310(19) Uani d . 1 . .
C C6 0.90683(15) 0.17311(12) 0.27485(6) 0.01074(18) Uani d . 1 . .
H H6A 0.9570 0.2001 0.3398 0.013 Uiso calc R 1 . .
C C7 0.71877(15) 0.03250(12) 0.26338(6) 0.01037(18) Uani d . 1 . .
H H7A 0.6112 0.0933 0.2644 0.012 Uiso calc R 1 . .
C C8 0.67731(15) -0.05984(12) 0.17062(6) 0.01066(18) Uani d . 1 . .
C C9 0.47820(15) -0.15295(12) 0.13264(6) 0.01103(18) Uani d . 1 . .
C C10 0.43704(15) -0.24679(13) 0.04013(7) 0.01356(19) Uani d . 1 . .
H H10A 0.3871 -0.1725 -0.0052 0.016 Uiso calc R 1 . .
H H10B 0.3363 -0.3499 0.0383 0.016 Uiso calc R 1 . .
C C11 0.61838(16) -0.29864(13) 0.01678(7) 0.01432(19) Uani d . 1 . .
H H11A 0.6579 -0.3863 0.0563 0.017 Uiso calc R 1 . .
H H11B 0.5882 -0.3473 -0.0451 0.017 Uiso calc R 1 . .
C C12 0.78507(16) -0.14125(13) 0.02780(7) 0.01329(19) Uani d . 1 . .
H H12A 0.9051 -0.1781 0.0224 0.016 Uiso calc R 1 . .
H H12B 0.7561 -0.0643 -0.0200 0.016 Uiso calc R 1 . .
C C13 0.81329(15) -0.04614(12) 0.11791(6) 0.01064(18) Uani d . 1 . .
C C14 0.71718(14) -0.09100(12) 0.33983(6) 0.01062(18) Uani d . 1 . .
C C15 0.72872(15) -0.02412(12) 0.42848(7) 0.01140(18) Uani d . 1 . .
C C16 0.72200(16) -0.13289(13) 0.49996(7) 0.01399(19) Uani d . 1 . .
H H16A 0.7337 -0.0869 0.5585 0.017 Uiso calc R 1 . .
C C17 0.69757(16) -0.31127(13) 0.48290(7) 0.0150(2) Uani d . 1 . .
H H17A 0.6903 -0.3844 0.5301 0.018 Uiso calc R 1 . .
C C18 0.68398(16) -0.38035(13) 0.39597(7) 0.0146(2) Uani d . 1 . .
H H18A 0.6674 -0.4992 0.3847 0.018 Uiso calc R 1 . .
C C19 0.69553(15) -0.26938(13) 0.32551(7) 0.01285(19) Uani d . 1 . .
H H19A 0.6886 -0.3158 0.2675 0.015 Uiso calc R 1 . .
C C20 0.79471(17) 0.22709(13) 0.52994(7) 0.0154(2) Uani d . 1 . .
H H20A 0.8251 0.3509 0.5289 0.023 Uiso calc R 1 . .
H H20B 0.9066 0.1875 0.5625 0.023 Uiso calc R 1 . .
H H20C 0.6861 0.1934 0.5593 0.023 Uiso calc R 1 . .
H H1O5 1.201(3) -0.067(2) 0.2552(12) 0.027(4) Uiso d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 O1 C1 . . 117.22(7) ?
C15 O4 C20 . . 116.87(8) ?
C1 O5 H1O5 . . 106.7(11) ?
O5 C1 O1 . . 107.99(7) ?
O5 C1 C2 . . 112.32(8) ?
O1 C1 C2 . . 104.81(7) ?
O5 C1 C6 . . 108.38(8) ?
O1 C1 C6 . . 109.47(8) ?
C2 C1 C6 . . 113.68(8) ?
C1 C2 C3 . . 113.12(9) ?
C1 C2 H2A . . 109.0 ?
C3 C2 H2A . . 109.0 ?
C1 C2 H2B . . 109.0 ?
C3 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
C2 C3 C4 . . 111.06(9) ?
C2 C3 H3A . . 109.4 ?
C4 C3 H3A . . 109.4 ?
C2 C3 H3B . . 109.4 ?
C4 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
C5 C4 C3 . . 109.20(8) ?
C5 C4 H4A . . 109.8 ?
C3 C4 H4A . . 109.8 ?
C5 C4 H4B . . 109.8 ?
C3 C4 H4B . . 109.8 ?
H4A C4 H4B . . 108.3 ?
O2 C5 C4 . . 122.38(9) ?
O2 C5 C6 . . 122.26(9) ?
C4 C5 C6 . . 115.35(9) ?
C5 C6 C1 . . 109.28(8) ?
C5 C6 C7 . . 111.86(8) ?
C1 C6 C7 . . 112.48(8) ?
C5 C6 H6A . . 107.7 ?
C1 C6 H6A . . 107.7 ?
C7 C6 H6A . . 107.7 ?
C8 C7 C14 . . 113.17(8) ?
C8 C7 C6 . . 109.55(8) ?
C14 C7 C6 . . 114.28(8) ?
C8 C7 H7A . . 106.4 ?
C14 C7 H7A . . 106.4 ?
C6 C7 H7A . . 106.4 ?
C13 C8 C9 . . 118.53(9) ?
C13 C8 C7 . . 122.45(9) ?
C9 C8 C7 . . 118.73(8) ?
O3 C9 C8 . . 121.80(9) ?
O3 C9 C10 . . 119.41(9) ?
C8 C9 C10 . . 118.74(9) ?
C9 C10 C11 . . 112.70(8) ?
C9 C10 H10A . . 109.1 ?
C11 C10 H10A . . 109.1 ?
C9 C10 H10B . . 109.1 ?
C11 C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.8 ?
C12 C11 C10 . . 110.02(8) ?
C12 C11 H11A . . 109.7 ?
C10 C11 H11A . . 109.7 ?
C12 C11 H11B . . 109.7 ?
C10 C11 H11B . . 109.7 ?
H11A C11 H11B . . 108.2 ?
C13 C12 C11 . . 110.92(8) ?
C13 C12 H12A . . 109.5 ?
C11 C12 H12A . . 109.5 ?
C13 C12 H12B . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.0 ?
O1 C13 C8 . . 123.96(9) ?
O1 C13 C12 . . 111.00(8) ?
C8 C13 C12 . . 125.03(9) ?
C19 C14 C15 . . 117.89(9) ?
C19 C14 C7 . . 122.94(8) ?
C15 C14 C7 . . 119.10(8) ?
O4 C15 C16 . . 123.04(9) ?
O4 C15 C14 . . 115.90(8) ?
C16 C15 C14 . . 121.05(9) ?
C17 C16 C15 . . 119.48(9) ?
C17 C16 H16A . . 120.3 ?
C15 C16 H16A . . 120.3 ?
C18 C17 C16 . . 120.50(9) ?
C18 C17 H17A . . 119.8 ?
C16 C17 H17A . . 119.8 ?
C17 C18 C19 . . 119.31(9) ?
C17 C18 H18A . . 120.3 ?
C19 C18 H18A . . 120.3 ?
C14 C19 C18 . . 121.74(9) ?
C14 C19 H19A . . 119.1 ?
C18 C19 H19A . . 119.1 ?
O4 C20 H20A . . 109.5 ?
O4 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O4 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C13 . 1.3529(12) ?
O1 C1 . 1.4570(11) ?
O2 C5 . 1.2148(13) ?
O3 C9 . 1.2345(12) ?
O4 C15 . 1.3718(12) ?
O4 C20 . 1.4350(12) ?
O5 C1 . 1.3962(11) ?
O5 H1O5 . 0.874(18) ?
C1 C2 . 1.5203(14) ?
C1 C6 . 1.5345(14) ?
C2 C3 . 1.5255(14) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.5378(16) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.5098(15) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.5344(13) ?
C6 C7 . 1.5412(14) ?
C6 H6A . 0.9800 ?
C7 C8 . 1.5133(13) ?
C7 C14 . 1.5276(13) ?
C7 H7A . 0.9800 ?
C8 C13 . 1.3574(14) ?
C8 C9 . 1.4607(14) ?
C9 C10 . 1.5151(13) ?
C10 C11 . 1.5253(15) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.5227(14) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.4982(13) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C14 C19 . 1.3931(13) ?
C14 C15 . 1.4091(13) ?
C15 C16 . 1.3964(13) ?
C16 C17 . 1.3961(14) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.3884(14) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.3976(14) ?
C18 H18A . 0.9300 ?
C19 H19A . 0.9300 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O5 H1O5 O3 1_655 0.87(2) 1.93(2) 2.7877(11) 166.3(18) yes
C6 H6A O4 . 0.98 2.32 2.9266(12) 120 yes
C16 H16A O5 2_756 0.93 2.53 3.4172(13) 160 yes
C20 H20B Cg1 2_756 0.96 2.67 3.5206(13) 147 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 O1 C1 O5 . . . . 71.99(10) ?
C13 O1 C1 C2 . . . . -168.09(8) ?
C13 O1 C1 C6 . . . . -45.81(10) ?
O5 C1 C2 C3 . . . . -175.06(8) ?
O1 C1 C2 C3 . . . . 67.95(10) ?
C6 C1 C2 C3 . . . . -51.54(11) ?
C1 C2 C3 C4 . . . . 54.04(11) ?
C2 C3 C4 C5 . . . . -55.21(12) ?
C3 C4 C5 O2 . . . . -122.06(11) ?
C3 C4 C5 C6 . . . . 56.91(11) ?
O2 C5 C6 C1 . . . . 125.76(10) ?
C4 C5 C6 C1 . . . . -53.20(11) ?
O2 C5 C6 C7 . . . . 0.54(13) ?
C4 C5 C6 C7 . . . . -178.43(8) ?
O5 C1 C6 C5 . . . . 174.47(8) ?
O1 C1 C6 C5 . . . . -67.98(10) ?
C2 C1 C6 C5 . . . . 48.83(11) ?
O5 C1 C6 C7 . . . . -60.66(10) ?
O1 C1 C6 C7 . . . . 56.89(10) ?
C2 C1 C6 C7 . . . . 173.70(8) ?
C5 C6 C7 C8 . . . . 82.61(9) ?
C1 C6 C7 C8 . . . . -40.82(10) ?
C5 C6 C7 C14 . . . . -149.21(8) ?
C1 C6 C7 C14 . . . . 87.36(10) ?
C14 C7 C8 C13 . . . . -114.03(10) ?
C6 C7 C8 C13 . . . . 14.77(12) ?
C14 C7 C8 C9 . . . . 72.27(11) ?
C6 C7 C8 C9 . . . . -158.94(8) ?
C13 C8 C9 O3 . . . . -170.97(9) ?
C7 C8 C9 O3 . . . . 2.98(14) ?
C13 C8 C9 C10 . . . . 6.60(13) ?
C7 C8 C9 C10 . . . . -179.45(8) ?
O3 C9 C10 C11 . . . . -156.92(9) ?
C8 C9 C10 C11 . . . . 25.45(12) ?
C9 C10 C11 C12 . . . . -53.49(11) ?
C10 C11 C12 C13 . . . . 50.03(11) ?
C1 O1 C13 C8 . . . . 20.22(13) ?
C1 O1 C13 C12 . . . . -160.09(8) ?
C9 C8 C13 O1 . . . . 169.98(8) ?
C7 C8 C13 O1 . . . . -3.74(15) ?
C9 C8 C13 C12 . . . . -9.66(14) ?
C7 C8 C13 C12 . . . . 176.62(9) ?
C11 C12 C13 O1 . . . . 160.59(8) ?
C11 C12 C13 C8 . . . . -19.73(13) ?
C8 C7 C14 C19 . . . . 4.92(14) ?
C6 C7 C14 C19 . . . . -121.40(10) ?
C8 C7 C14 C15 . . . . -171.98(9) ?
C6 C7 C14 C15 . . . . 61.70(12) ?
C20 O4 C15 C16 . . . . 12.66(14) ?
C20 O4 C15 C14 . . . . -168.10(9) ?
C19 C14 C15 O4 . . . . -178.20(9) ?
C7 C14 C15 O4 . . . . -1.14(14) ?
C19 C14 C15 C16 . . . . 1.06(15) ?
C7 C14 C15 C16 . . . . 178.12(9) ?
O4 C15 C16 C17 . . . . 177.27(10) ?
C14 C15 C16 C17 . . . . -1.94(16) ?
C15 C16 C17 C18 . . . . 1.30(16) ?
C16 C17 C18 C19 . . . . 0.17(16) ?
C15 C14 C19 C18 . . . . 0.46(15) ?
C7 C14 C19 C18 . . . . -176.48(9) ?
C17 C18 C19 C14 . . . . -1.07(16) ?
