data_2012186 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1095 _journal_page_last 1097 _publ_section_title ; 6-Deoxyjacareubin ; loop_ _publ_author_name 'Doriguetto, Antonio C.' 'Santos, Marcelo H.' 'Ellena, Javier A.' 'Nagem, Tanus J.' _chemical_name_common '6-dehydroxyjacareubin' _chemical_formula_moiety 'C18 H14 O5' _chemical_formula_sum 'C18 H14 O5' _chemical_formula_weight 310.29 _chemical_melting_point '503-505 K' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4450(2) _cell_length_b 9.5200(3) _cell_length_c 10.9390(3) _cell_angle_alpha 105.051(2) _cell_angle_beta 103.154(2) _cell_angle_gamma 93.083(2) _cell_volume 723.80(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.424 _diffrn_ambient_temperature 293(2) loop_ _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 _atom_site_type_symbol O1 .20011(17) -.51755(16) -.19870(14) .0491(4) Uani d . 1 . . O H1' .269(5) -.439(3) -.146(3) .095(10) Uiso d . 1 . . H O2 -.49153(16) -.32309(15) -.04343(14) .0524(4) Uani d . 1 . . O O3 -.41897(18) -.08552(18) .14370(17) .0621(5) Uani d . 1 . . O H3' -.481(5) -.162(4) .079(3) .108(11) Uiso d . 1 . . H O4 .20030(17) .14926(13) .27926(12) .0418(3) Uani d . 1 . . O O5 .05941(15) -.29604(12) -.04833(11) .0351(3) Uani d . 1 . . O C1 .0187(2) -.52917(18) -.19702(16) .0351(4) Uani d . 1 . . C C2 -.0936(2) -.65696(19) -.27140(17) .0394(4) Uani d . 1 . . C H2 -.0433 -.7316 -.3214 .047 Uiso calc R 1 . . H C3 -.2806(2) -.67601(19) -.27285(17) .0409(4) Uani d . 1 . . C H3 -.3536 -.7631 -.3234 .049 Uiso calc R 1 . . H C4 -.3585(2) -.56726(19) -.20019(17) .0392(4) Uani d . 1 . . C H4 -.4838 -.5803 -.2019 .047 Uiso calc R 1 . . H C5 -.2478(2) -.43641(18) -.12333(16) .0336(3) Uani d . 1 . . C C6 -.3222(2) -.31847(19) -.04209(17) .0363(4) Uani d . 1 . . C C7 -.1897(2) -.19686(18) .04208(16) .0341(3) Uani d . 1 . . C C8 -.2418(2) -.0822(2) .13413(18) .0395(4) Uani d . 1 . . C C9 -.1133(2) .03402(19) .21636(17) .0380(4) Uani d . 1 . . C C10 -.1599(3) .1591(2) .30798(19) .0478(5) Uani d . 1 . . C H10 -.2833 .1739 .3042 .057 Uiso calc R 1 . . H C11 -.0236(3) .2516(2) .39687(19) .0485(5) Uani d . 1 . . C H11 -.0518 .3347 .4524 .058 Uiso calc R 1 . . H C12 .1758(3) .22398(19) .40898(17) .0428(4) Uani d . 1 . . C C13 .3071(3) .3651(2) .4532(2) .0537(5) Uani d . 1 . . C H13A .3067 .4167 .5410 .081 Uiso calc R 1 . . H H13B .2674 .4252 .3963 .081 Uiso calc R 1 . . H H13C .4305 .3427 .4502 .081 Uiso calc R 1 . . H C14 .2330(3) .1254(2) .4971(2) .0547(5) Uani d . 1 . . C H14A .2322 .1758 .5852 .082 Uiso calc R 1 . . H H14B .3558 .1009 .4945 .082 Uiso calc R 1 . . H H14C .1473 .0374 .4672 .082 Uiso calc R 1 . . H C15 .0706(2) .03511(18) .20446(16) .0346(4) Uani d . 1 . . C C16 .1272(2) -.07304(17) .11465(16) .0339(3) Uani d . 1 . . C H16 .2494 -.0683 .1075 .041 Uiso calc R 1 . . H C17 -.0034(2) -.18804(17) .03607(15) .0312(3) Uani d . 1 . . C C18 -.0604(2) -.41890(17) -.12208(15) .0316(3) Uani d . 1 . . C 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 .0284(6) .0482(8) .0594(8) .0008(5) .0134(6) -.0058(6) O2 .0242(6) .0544(8) .0643(9) -.0020(5) .0104(6) -.0061(7) O3 .0270(6) .0644(9) .0758(10) .0003(6) .0175(7) -.0165(8) O4 .0373(6) .0388(6) .0401(7) -.0070(5) .0074(5) -.0008(5) O5 .0257(5) .0341(6) .0397(6) -.0007(4) .0083(4) .0007(5) C1 .0283(7) .0380(8) .0362(8) .0031(6) .0066(6) .0070(7) C2 .0371(9) .0370(9) .0381(9) .0048(7) .0063(7) .0029(7) C3 .0354(8) .0365(8) .0415(9) -.0028(7) .0016(7) .0031(7) C4 .0290(8) .0406(9) .0416(9) -.0028(7) .0043(7) .0061(7) C5 .0266(7) .0362(8) .0340(8) .0001(6) .0041(6) .0065(6) C6 .0244(7) .0407(9) .0397(9) .0008(6) .0068(6) .0059(7) C7 .0243(7) .0366(8) .0370(8) .0011(6) .0060(6) .0048(7) C8 .0259(8) .0444(9) .0435(9) .0036(7) .0093(7) .0039(7) C9 .0311(8) .0390(9) .0387(9) .0032(7) .0073(7) .0032(7) C10 .0408(9) .0472(10) .0485(10) .0077(8) .0121(8) .0001(8) C11 .0520(11) .0427(10) .0433(10) .0063(8) .0116(8) -.0005(8) C12 .0450(10) .0395(9) .0358(9) -.0020(7) .0051(7) .0024(7) C13 .0599(12) .0429(10) .0450(10) -.0104(9) .0021(9) .0021(8) C14 .0554(12) .0548(12) .0506(11) .0007(9) .0055(9) .0169(9) C15 .0305(8) .0337(8) .0348(8) -.0010(6) .0034(6) .0066(6) C16 .0249(7) .0355(8) .0382(8) -.0004(6) .0063(6) .0069(7) C17 .0267(7) .0324(8) .0333(8) .0038(6) .0072(6) .0071(6) C18 .0277(7) .0319(8) .0311(7) .0001(6) .0038(6) .0057(6) 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 C1 . 1.354(2) YES O1 H1' . .87(3) NO O2 C6 . 1.255(2) NO O3 C8 . 1.346(2) YES O3 H3' . .89(3) NO O4 C15 . 1.360(2) YES O4 C12 . 1.470(2) YES O5 C17 . 1.373(2) NO O5 C18 . 1.373(2) NO C1 C2 . 1.381(2) NO C1 C18 . 1.400(2) NO C2 C3 . 1.390(2) NO C3 C4 . 1.374(2) NO C4 C5 . 1.403(2) NO C5 C18 . 1.392(2) NO C5 C6 . 1.460(2) NO C6 C7 . 1.439(2) NO C7 C17 . 1.402(2) NO C7 C8 . 1.418(2) NO C8 C9 . 1.388(2) NO C9 C15 . 1.404(2) NO C9 C10 . 1.458(2) YES C10 C11 . 1.327(3) YES C11 C12 . 1.504(3) YES C12 C13 . 1.517(2) YES C12 C14 . 1.522(3) YES C15 C16 . 1.383(2) NO C16 C17 . 1.378(2) NO