data_2007032 _journal_data_validation_number ? _journal_name_full 'Acta Crystallographica' _journal_year 1998 _journal_volume C54 _publ_section_title ; 2,3-Dihydro-8-hydroxy-5,7-dimethoxy-2-phenyl-4H-1-benzopyran-4-one and 3,3,6-Tribromo-2,3-dihydro-8-hydroxy-5,7-dimethoxy-2-phenyl-4H-1-benzopyran- 4-one ; loop_ _publ_author_name 'Kan Chantrapromma' 'Vatcharee Seechamnanturakit' 'Chaveng Pakawatchai' 'Suchada Chantrapromma' 'Kandasamy Chinnakali' 'Hoong-Kun Fun' _chemical_formula_moiety 'C17 H16 O5' _chemical_formula_sum 'C17 H16 O5' _chemical_formula_weight 300.30 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 36.858(5) _cell_length_b 6.5975(10) _cell_length_c 12.145(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.255(10) _cell_angle_gamma 90.00 _cell_volume 2896.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.377 _diffrn_ambient_temperature 293(2) _refine_ls_R_factor_obs .0881 _refine_ls_wR_factor_obs .3023 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .36286(13) .0974(6) .9828(3) .0481(12) Uani d . 1 . O C2 .3533(2) -.1161(10) .9855(5) .051(2) Uani d . 1 . C C3 .3443(2) -.1951(11) .8683(5) .054(2) Uani d . 1 . C H3A .3214(2) -.1335(11) .8302(5) .065 Uiso calc R 1 . H H3B .3402(2) -.3401(11) .8710(5) .065 Uiso calc R 1 . H C4 .3734(2) -.1566(9) .8009(5) .045(2) Uani d . 1 . C C5 .4217(2) .1033(8) .7719(4) .0395(14) Uani d . 1 . C C6 .4395(2) .2862(9) .8004(5) .043(2) Uani d . 1 . C C7 .4329(2) .3931(8) .8933(5) .0418(15) Uani d . 1 . C C8 .4074(2) .3252(9) .9544(5) .047(2) Uani d . 1 . C C9 .3880(2) .1464(8) .9211(4) .0381(14) Uani d . 1 . C C10 .3951(2) .0297(8) .8296(5) .0393(14) Uani d . 1 . C O11 .37779(14) -.2772(7) .7278(4) .0575(14) Uani d . 1 . O O12 .42852(12) -.0082(6) .6831(3) .0484(12) Uani d . 1 . O C13 .4534(2) .0721(12) .6180(6) .051(2) Uani d . 1 . C O14 .45010(14) .5699(6) .9311(4) .0571(14) Uani d . 1 . O C15 .4759(3) .6529(12) .8705(7) .063(2) Uani d . 1 . C O16 .4023(2) .4316(7) 1.0463(4) .0604(15) Uani d . 1 . O C17 .3231(2) -.1313(10) 1.0515(6) .052(2) Uani d . 1 . C C18 .2928(3) -.0071(13) 1.0360(7) .070(2) Uani d . 1 . C C19 .2654(3) -.0251(15) 1.0973(8) .079(3) Uani d . 1 . C C20 .2674(2) -.1772(14) 1.1749(7) .072(2) Uani d . 1 . C C21 .2978(3) -.2985(16) 1.1930(9) .088(3) Uani d . 1 . C C22 .3248(2) -.2820(13) 1.1306(7) .070(2) Uani d . 1 . C H2 .378(2) -.183(12) 1.035(7) .07(2) Uiso d . 1 . H H6 .4609(16) .324(9) .763(5) .040(15) Uiso d . 1 . H H13A .474(2) .080(12) .663(7) .06(2) Uiso d . 1 . H H13B .4440(17) .208(11) .586(6) .051(18) Uiso d . 1 . H H13C .4539(15) -.042(10) .552(5) .043(16) Uiso d . 1 . H H15A .4997(18) .569(10) .866(5) .049(18) Uiso d . 1 . H H15B .485(2) .784(14) .902(7) .09(3) Uiso d . 1 . H H15C .466(2) .652(13) .788(8) .08(3) Uiso d . 1 . H H16 .396(3) .339(17) 1.099(9) .13(4) Uiso d . 1 . H H18 .294(3) .102(15) .988(8) .10(3) Uiso d . 1 . H H19 .247(2) .064(13) 1.084(7) .08(3) Uiso d . 1 . H H20 .246(2) -.176(11) 1.227(6) .07(2) Uiso d . 1 . H H21 .291(5) -.44(3) 1.216(14) .22(7) Uiso d . 1 . H H22 .348(3) -.372(14) 1.135(7) .09(3) Uiso d . 1 . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 .080(3) .030(2) .038(2) -.007(2) .021(2) -.003(2) C2 .075(5) .033(3) .044(3) -.011(3) .012(3) -.001(3) C3 .072(4) .049(4) .042(3) -.016(3) .010(3) -.006(3) C4 .078(4) .028(3) .029(3) .000(3) .010(3) -.004(3) C5 .064(4) .026(3) .028(3) .007(3) .009(3) .006(2) C6 .069(4) .031(3) .030(3) .000(3) .011(3) .003(2) C7 .069(4) .024(3) .032(3) -.001(3) .010(3) -.001(2) C8 .083(5) .026(3) .034(3) .001(3) .016(3) .002(2) C9 .060(4) .027(3) .028(3) -.001(3) .008(3) .004(2) C10 .061(4) .026(3) .029(3) .001(3) .005(3) .002(2) O11 .097(4) .037(2) .042(2) -.015(2) .021(2) -.012(2) O12 .081(3) .037(2) .030(2) -.001(2) .019(2) -.005(2) C13 .060(4) .057(5) .036(3) -.005(4) .012(3) -.007(3) O14 .097(4) .029(2) .051(3) -.020(2) .029(3) -.010(2) C15 .091(6) .037(4) .066(5) -.018(4) .027(4) -.001(4) O16 .115(4) .029(2) .046(3) -.009(2) .036(3) -.009(2) C17 .066(4) .040(4) .052(4) -.005(3) .018(3) -.008(3) C18 .101(6) .050(5) .064(5) .010(4) .032(5) .015(4) C19 .089(6) .070(6) .083(6) .028(5) .031(5) .008(5) C20 .077(5) .078(6) .067(5) -.014(5) .027(4) .000(4) C21 .094(7) .081(7) .095(7) .006(6) .036(6) .037(5) C22 .067(5) .064(5) .080(6) .008(4) .017(4) .021(4) 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 C9 . 1.340(7) yes O1 C2 . 1.454(7) yes C2 C3 . 1.491(9) yes C2 C17 . 1.498(10) ? C3 C4 . 1.493(9) yes C4 O11 . 1.225(7) yes C4 C10 . 1.471(8) yes C5 O12 . 1.369(7) yes C5 C6 . 1.386(8) yes C5 C10 . 1.397(9) yes C6 C7 . 1.391(8) yes C7 O14 . 1.364(7) yes C7 C8 . 1.382(9) yes C8 O16 . 1.362(7) yes C8 C9 . 1.397(8) yes C9 C10 . 1.418(8) yes O12 C13 . 1.424(8) ? O14 C15 . 1.422(9) ? C17 C18 . 1.368(11) ? C17 C22 . 1.376(10) ? C18 C19 . 1.370(12) ? C19 C20 . 1.368(12) ? C20 C21 . 1.362(13) ? C21 C22 . 1.365(12) ?