#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/34/2223492.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_2223492
loop_
_publ_author_name
'Deesamer, Sujittra'
'Chavasiri, Warinthorn'
'Chaichit, Narongsak'
'Muangsin, Nongnuj'
'Kokpol, Udom'
_publ_section_title
;9-Methoxy-6a,11a-dimethyl-6a,11a-dihydro-6H-1-benzofuro[3,2-c]chromen-3-ol
 from Dalbergia oliveri
;
_journal_coeditor_code           NG2631
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2387
_journal_paper_doi               10.1107/S1600536809034485
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H14 O4'
_chemical_formula_moiety         'C16 H14 O4'
_chemical_formula_sum            'C16 H14 O4'
_chemical_formula_weight         270.27
_chemical_name_common
;
(+)-(6aS,11aS)-medicarpin
;
_chemical_name_systematic
;
9-Methoxy-6a,11a-dimethyl-6a,11a-dihydro-6H-\
1-benzofuro[3,2-c]chromen-3-ol from Dalbergia Oliveri
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.4820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6289(3)
_cell_length_b                   8.7963(4)
_cell_length_c                   11.3150(5)
_cell_measurement_temperature    293(2)
_cell_volume                     650.76(5)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'SMART (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       ω
_diffrn_radiation_source         Mo
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4783
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         30.41
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1949
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.0162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0926
_reflns_number_gt                1949
_reflns_number_total             3198
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2631.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2223492
_cod_database_fobs_code          2223492
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
C C1 0.0057(2) 0.4390(2) 0.69102(16) 0.0414(4) Uani d . 1 . .
H H1 -0.1252 0.398 0.6736 0.05 Uiso calc R 1 . .
C C2 0.0496(3) 0.5393(3) 0.78509(16) 0.0458(4) Uani d . 1 . .
H H2 -0.0512 0.5664 0.8294 0.055 Uiso calc R 1 . .
C C3 0.2455(3) 0.6001(2) 0.81356(14) 0.0413(4) Uani d . 1 . .
C C4 0.3960(3) 0.5576(2) 0.74813(15) 0.0399(4) Uani d . 1 . .
H H4 0.5278 0.5962 0.7678 0.048 Uiso calc R 1 . .
C C4A 0.3482(2) 0.45666(19) 0.65285(14) 0.0351(3) Uani d . 1 . .
C C6 0.4820(3) 0.2767(2) 0.53202(17) 0.0426(4) Uani d . 1 . .
H H6A 0.4918 0.1964 0.5915 0.051 Uiso calc R 1 . .
H H6B 0.5928 0.2632 0.4867 0.051 Uiso calc R 1 . .
C C6A 0.2800(2) 0.26311(19) 0.44829(15) 0.0365(3) Uani d . 1 . .
H H6A1 0.2669 0.1601 0.4149 0.044 Uiso calc R 1 . .
C C6B 0.2447(2) 0.37674(19) 0.34730(14) 0.0338(3) Uani d . 1 . .
C C7 0.3662(3) 0.4270(2) 0.26630(15) 0.0393(3) Uani d . 1 . .
H H7 0.5007 0.3937 0.2723 0.047 Uiso calc R 1 . .
C C8 0.2854(3) 0.5275(2) 0.17639(16) 0.0424(4) Uani d . 1 . .
H H8 0.367 0.5633 0.123 0.051 Uiso calc R 1 . .
C C9 0.0829(3) 0.5752(2) 0.16556(14) 0.0388(4) Uani d . 1 . .
C C10 -0.0419(3) 0.5288(2) 0.24674(15) 0.0374(3) Uani d . 1 . .
H H10 -0.1764 0.5621 0.2409 0.045 Uiso calc R 1 . .
C C10A 0.0455(2) 0.43038(19) 0.33679(13) 0.0332(3) Uani d . 1 . .
C C11A 0.0957(2) 0.29610(19) 0.51234(15) 0.0363(3) Uani d . 1 . .
H H11A 0.0382 0.2002 0.5358 0.044 Uiso calc R 1 . .
C C11B 0.1513(2) 0.39649(18) 0.62068(14) 0.0343(3) Uani d . 1 . .
C C12 -0.1997(3) 0.7026(3) 0.04448(19) 0.0579(5) Uani d . 1 . .
H H12A -0.2266 0.7714 -0.0221 0.087 Uiso calc R 1 . .
H H12B -0.2447 0.7474 0.113 0.087 Uiso calc R 1 . .
H H12C -0.2719 0.6091 0.0244 0.087 Uiso calc R 1 . .
O O1 0.50439(17) 0.42138(16) 0.59175(11) 0.0436(3) Uani d . 1 . .
O O2 -0.05777(17) 0.37602(17) 0.42345(10) 0.0401(3) Uani d . 1 . .
O O3 0.0152(2) 0.67276(19) 0.07158(11) 0.0518(4) Uani d . 1 . .
O O4 0.2992(2) 0.7012(2) 0.90549(12) 0.0550(4) Uani d . 1 . .
H H4A 0.2102 0.7028 0.9479 0.083 Uiso calc R 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 '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
C2 C1 C11B . . 122.26(15) ?
C2 C1 H1 . . 118.9 ?
C11B C1 H1 . . 118.9 ?
C1 C2 C3 . . 119.68(17) ?
C1 C2 H2 . . 120.2 ?
C3 C2 H2 . . 120.2 ?
O4 C3 C4 . . 117.40(16) ?
O4 C3 C2 . . 122.73(17) ?
C4 C3 C2 . . 119.87(17) ?
C3 C4 C4A . . 119.56(15) ?
C3 C4 H4 . . 120.2 ?
C4A C4 H4 . . 120.2 ?
O1 C4A C4 . . 116.13(14) ?
O1 C4A C11B . . 122.15(14) ?
C4 C4A C11B . . 121.72(14) ?
O1 C6 C6A . . 112.14(14) ?
O1 C6 H6A . . 109.2 ?
C6A C6 H6A . . 109.2 ?
O1 C6 H6B . . 109.2 ?
C6A C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
C6B C6A C6 . . 115.68(14) ?
C6B C6A C11A . . 101.24(12) ?
C6 C6A C11A . . 112.20(14) ?
C6B C6A H6A1 . . 109.1 ?
C6 C6A H6A1 . . 109.1 ?
C11A C6A H6A1 . . 109.1 ?
C7 C6B C10A . . 118.82(15) ?
C7 C6B C6A . . 132.64(14) ?
C10A C6B C6A . . 108.46(13) ?
C8 C7 C6B . . 119.42(15) ?
C8 C7 H7 . . 120.3 ?
C6B C7 H7 . . 120.3 ?
C7 C8 C9 . . 120.45(16) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
O3 C9 C8 . . 116.15(16) ?
O3 C9 C10 . . 122.38(15) ?
C8 C9 C10 . . 121.46(16) ?
C10A C10 C9 . . 116.39(15) ?
C10A C10 H10 . . 121.8 ?
C9 C10 H10 . . 121.8 ?
O2 C10A C6B . . 113.57(14) ?
O2 C10A C10 . . 123.03(14) ?
C6B C10A C10 . . 123.39(15) ?
O2 C11A C11B . . 108.81(14) ?
O2 C11A C6A . . 106.09(13) ?
C11B C11A C6A . . 112.62(13) ?
O2 C11A H11A . . 109.7 ?
C11B C11A H11A . . 109.7 ?
C6A C11A H11A . . 109.7 ?
C1 C11B C4A . . 116.87(15) ?
C1 C11B C11A . . 121.33(14) ?
C4A C11B C11A . . 121.74(14) ?
O3 C12 H12A . . 109.5 ?
O3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C4A O1 C6 . . 114.15(13) ?
C10A O2 C11A . . 106.43(12) ?
C9 O3 C12 . . 117.65(15) ?
C3 O4 H4A . . 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
C1 C2 . 1.376(3) ?
C1 C11B . 1.399(2) ?
C1 H1 . 0.93 ?
C2 C3 . 1.393(3) ?
C2 H2 . 0.93 ?
C3 O4 . 1.370(2) ?
C3 C4 . 1.388(3) ?
C4 C4A . 1.392(2) ?
C4 H4 . 0.93 ?
C4A O1 . 1.372(2) ?
C4A C11B . 1.400(2) ?
C6 O1 . 1.437(2) ?
C6 C6A . 1.512(2) ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C6A C6B . 1.507(2) ?
C6A C11A . 1.547(2) ?
C6A H6A1 . 0.98 ?
C6B C7 . 1.389(2) ?
C6B C10A . 1.389(2) ?
C7 C8 . 1.387(3) ?
C7 H7 . 0.93 ?
C8 C9 . 1.393(2) ?
C8 H8 . 0.93 ?
C9 O3 . 1.382(2) ?
C9 C10 . 1.395(2) ?
C10 C10A . 1.389(2) ?
C10 H10 . 0.93 ?
C10A O2 . 1.3709(19) ?
C11A O2 . 1.484(2) ?
C11A C11B . 1.507(2) ?
C11A H11A . 0.98 ?
C12 O3 . 1.431(3) ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
O4 H4A . 0.82 ?
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
O4 H4A O3 1_556 0.82 2.07 2.882(2) 169.2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 65860
