#------------------------------------------------------------------------------ #$Date: 2025-08-21 21:04:39 +0100 (Thu, 21 Aug 2025) $ #$Revision: 301851 $ #$URL: svn://www.crystallography.net/cod/cif/7/05/12/7051225.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_7051225 loop_ _publ_author_name 'Braga, Dario' 'Cojazzi, Gianna' 'Maini, Lucia' 'Grepioni, Fabrizia' _publ_section_title ; Reversible solid-state interconversion of rhodizonic acid H2C6O6 into H6C6O8 and the solid-state structure of the rhodizonate dianion C6O62-- (aromatic or non-aromatic?) ; _journal_issue 10 _journal_name_full 'New Journal of Chemistry' _journal_page_first 1221 _journal_paper_doi 10.1039/b107317f _journal_volume 25 _journal_year 2001 _chemical_formula_sum 'C6 H6 O8' _chemical_formula_weight 206.11 _chemical_name_common 'Rhodizonic acid dihydrate' _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 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 91.796(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 11.2163(13) _cell_length_b 9.6120(12) _cell_length_c 12.786(2) _cell_measurement_temperature 223(2) _cell_volume 1377.8(3) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 223(2) _diffrn_measured_fraction_theta_full 0.923 _diffrn_measured_fraction_theta_max 0.923 _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 0.1276 _diffrn_reflns_av_sigmaI/netI 0.1551 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 9624 _diffrn_reflns_theta_full 33.95 _diffrn_reflns_theta_max 33.95 _diffrn_reflns_theta_min 2.79 _exptl_absorpt_coefficient_mu 0.193 _exptl_absorpt_correction_type 'Bruker absorption correction' _exptl_crystal_density_diffrn 1.987 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _refine_diff_density_max 0.526 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.091 _refine_ls_extinction_coef 0.0029(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.730 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 152 _refine_ls_number_reflns 2589 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.730 _refine_ls_R_factor_all 0.1436 _refine_ls_R_factor_gt 0.0592 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1194 _refine_ls_wR_factor_ref 0.1462 _reflns_number_gt 1219 _reflns_number_total 2589 _reflns_threshold_expression >2sigma(I) _cod_data_source_file b107317f.txt _cod_data_source_block 1 _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 C2/c _cod_database_code 7051225 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' 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 0.54949(15) 0.46317(18) 0.12446(15) 0.0179(4) Uani 1 1 d . . . H1 H 0.578(3) 0.549(3) 0.125(2) 0.017(7) Uiso 1 1 d . . . O2 O 0.41445(16) 0.69842(17) 0.12742(16) 0.0227(4) Uani 1 1 d . . . O3A O 0.21427(17) 0.56870(18) -0.01194(13) 0.0174(4) Uani 1 1 d . . . H31 H 0.140(3) 0.547(4) -0.026(3) 0.044(11) Uiso 1 1 d . . . O3B O 0.17288(16) 0.70215(16) 0.13558(14) 0.0156(4) Uani 1 1 d . . . H32 H 0.216(4) 0.771(4) 0.125(3) 0.067(14) Uiso 1 1 d . . . O4A O 0.18712(17) 0.46878(18) 0.26242(14) 0.0180(4) Uani 1 1 d . . . H41 H 0.156(3) 0.541(4) 0.279(3) 0.047(11) Uiso 1 1 d . . . O4B O 0.05609(15) 0.44396(17) 0.11753(15) 0.0172(4) Uani 1 1 d . . . H42 H 0.038(3) 0.361(4) 0.132(3) 0.049(11) Uiso 1 1 d . . . O5 O 0.19167(15) 0.21210(16) 0.11862(14) 0.0180(4) Uani 1 1 d . . . O6 O 0.43038(16) 0.20778(17) 0.12869(15) 0.0183(4) Uani 1 1 d . . . H6 H 0.506(5) 0.225(5) 0.138(4) 0.11(2) Uiso 1 1 d . . . C1 C 0.4297(2) 0.4567(2) 0.12278(18) 0.0123(5) Uani 1 1 d . . . C2 C 0.3627(2) 0.5878(2) 0.11872(18) 0.0130(5) Uani 1 1 d . . . C3 C 0.2282(2) 0.5815(2) 0.09724(18) 0.0113(4) Uani 1 1 d . . . C4 C 0.1741(2) 0.4556(2) 0.15323(18) 0.0119(4) Uani 1 1 d . . . C5 C 0.2442(2) 0.3225(2) 0.12925(18) 0.0113(4) Uani 1 1 d . . . C6 C 0.3738(2) 0.3312(2) 0.12649(18) 0.0128(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0085(9) 0.0149(8) 0.0304(10) 0.0015(7) 0.0013(7) -0.0012(7) O2 0.0150(10) 0.0132(8) 0.0401(12) 0.0005(8) 0.0017(8) -0.0024(7) O3A 0.0184(10) 0.0218(9) 0.0120(8) 0.0017(7) -0.0025(7) -0.0005(7) O3B 0.0147(9) 0.0089(7) 0.0233(9) -0.0006(6) 0.0037(7) 0.0021(7) O4A 0.0260(11) 0.0151(8) 0.0130(8) -0.0007(6) 0.0038(7) 0.0015(7) O4B 0.0096(9) 0.0128(8) 0.0292(10) 0.0031(7) 0.0005(7) -0.0006(6) O5 0.0140(9) 0.0133(7) 0.0266(10) -0.0017(7) 0.0000(7) -0.0017(7) O6 0.0137(10) 0.0119(7) 0.0296(10) 0.0022(7) 0.0024(8) 0.0037(7) C1 0.0099(11) 0.0141(9) 0.0130(11) -0.0004(8) 0.0003(8) 0.0007(9) C2 0.0139(12) 0.0113(9) 0.0139(11) 0.0004(8) 0.0029(9) -0.0004(8) C3 0.0138(12) 0.0101(9) 0.0099(10) -0.0005(7) 0.0004(8) 0.0017(8) C4 0.0116(11) 0.0099(8) 0.0142(11) 0.0004(8) 0.0013(9) -0.0002(8) C5 0.0125(12) 0.0119(9) 0.0094(10) 0.0019(8) -0.0011(8) 0.0014(8) C6 0.0119(12) 0.0120(10) 0.0146(11) -0.0004(8) 0.0007(9) 0.0010(8) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 113.7(19) . . ? C3 O3A H31 108(2) . . ? C3 O3B H32 109(3) . . ? C4 O4A H41 108(3) . . ? C4 O4B H42 104(2) . . ? C6 O6 H6 107(3) . . ? O1 C1 C6 120.1(2) . . ? O1 C1 C2 118.13(19) . . ? C6 C1 C2 121.8(2) . . ? O2 C2 C1 120.4(2) . . ? O2 C2 C3 121.2(2) . . ? C1 C2 C3 118.34(19) . . ? O3B C3 O3A 112.42(18) . . ? O3B C3 C2 110.37(18) . . ? O3A C3 C2 105.09(18) . . ? O3B C3 C4 107.49(18) . . ? O3A C3 C4 111.07(18) . . ? C2 C3 C4 110.43(18) . . ? O4B C4 O4A 113.70(18) . . ? O4B C4 C5 110.79(18) . . ? O4A C4 C5 103.59(18) . . ? O4B C4 C3 107.18(18) . . ? O4A C4 C3 111.14(18) . . ? C5 C4 C3 110.47(18) . . ? O5 C5 C6 121.8(2) . . ? O5 C5 C4 119.8(2) . . ? C6 C5 C4 118.26(19) . . ? O6 C6 C1 124.4(2) . . ? O6 C6 C5 114.76(19) . . ? C1 C6 C5 120.9(2) . . ? 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 1.344(3) . ? O1 H1 0.88(3) . ? O2 C2 1.214(3) . ? O3A C3 1.405(3) . ? O3A H31 0.87(4) . ? O3B C3 1.410(3) . ? O3B H32 0.84(4) . ? O4A C4 1.405(3) . ? O4A H41 0.81(3) . ? O4B C4 1.391(3) . ? O4B H42 0.85(4) . ? O5 C5 1.219(3) . ? O6 C6 1.346(3) . ? O6 H6 0.87(5) . ? C1 C6 1.361(3) . ? C1 C2 1.467(3) . ? C2 C3 1.527(3) . ? C3 C4 1.541(3) . ? C4 C5 1.538(3) . ? C5 C6 1.457(3) . ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21142332 2 PubChem 13380470