#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/20/2012015.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_2012015 loop_ _publ_author_name 'Jene, Paul G.' 'Pernin, Christopher G.' 'Ibers, James A.' _publ_section_title ; Comparison of conventional and synchrotron X-ray structure determinations of the adduct 1,2,4,5-tetrahydroxybenzene--2,5-dihydroxy-1,4-benzoquinone (1/1) and a conventional X-ray structure determination of 1,2,4,5-tetrahydroxybenzene monohydrate ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 730 _journal_page_last 734 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C6 H6 O4 , C6 H4 O4' _chemical_formula_sum 'C12 H10 O8' _chemical_formula_weight 282.20 _chemical_melting_point_gt 673 _chemical_name_systematic ; 1,2,4,5-Tetrahydroxybenzene-2,5-Dihydroxy-1,4-benzoquinone (1/1) ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 105.7780(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.3820(10) _cell_length_b 6.0650(10) _cell_length_c 12.1970(10) _cell_measurement_reflns_used 4909 _cell_measurement_temperature 110(2) _cell_measurement_theta_max 25.88 _cell_measurement_theta_min 2.55 _cell_volume 525.51(12) _computing_cell_refinement HKL _computing_data_collection 'HKL (Otwinowski & Minor, 1997)' _computing_data_reduction HKL _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1997b)' _computing_publication_material SHELXTL/PC _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 110(2) _diffrn_measured_fraction_theta_full .950 _diffrn_measured_fraction_theta_max .689 _diffrn_measurement_device_type 'R-axis IV image plate' _diffrn_measurement_method \f _diffrn_radiation_monochromator 'silicon crystal' _diffrn_radiation_source white-beam _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength .35400 _diffrn_reflns_av_R_equivalents .032 _diffrn_reflns_av_sigmaI/netI .030 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 13465 _diffrn_reflns_theta_full 20.73 _diffrn_reflns_theta_max 25.88 _diffrn_reflns_theta_min 2.55 _diffrn_standards_decay_% <2 _exptl_absorpt_coefficient_mu .092 _exptl_absorpt_correction_type none _exptl_crystal_colour black _exptl_crystal_density_diffrn 1.783 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 292 _exptl_crystal_size_max 1.12 _exptl_crystal_size_mid .33 _exptl_crystal_size_min .20 _refine_diff_density_max .58 _refine_diff_density_min -.48 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 94 _refine_ls_number_reflns 5678 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.04 _refine_ls_R_factor_all .036 _refine_ls_R_factor_gt .031 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0738P)^2^+0.021P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .113 _reflns_number_gt 4908 _reflns_number_total 5678 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file da1173.cif _[local]_cod_data_source_block IIb _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_melting_point_gt' since the value was specified 'more than' ('>') a certain temperature. The value '>673' was changed to '673' - it should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_melting_point_gt' since the value was specified 'more than' ('>') a certain temperature. The value '>673' was changed to '673' - it should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012015 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 .98001(3) .55561(4) -.227606(18) .01002(4) Uani d . 1 . . O H1 .9364 .4433 -.2660 .012 Uiso calc R 1 . . H O2 .82605(3) .15883(3) .081429(18) .00871(4) Uani d . 1 . . O H3 .7803 .0668 .0299 .010 Uiso calc R 1 . . H O3 .99517(3) -.06236(4) .276231(17) .00943(4) Uani d . 1 . . O H5 .9432 .0400 .2325 .011 Uiso calc R 1 . . H O4 1.16100(3) -.34706(3) .431529(19) .00904(4) Uani d . 1 . . O C1 .98744(3) .51993(4) -.11610(2) .00659(4) Uani d . 1 . . C C2 .89983(3) .34416(4) -.07772(2) .00687(4) Uani d . 1 . . C H2 .8317 .2380 -.1302 .008 Uiso calc R 1 . . H C3 .91252(3) .32451(4) .03811(2) .00647(4) Uani d . 1 . . C C4 .90645(3) .16006(4) .41520(2) .00727(4) Uani d . 1 . . C H4 .8443 .2663 .3606 .009 Uiso calc R 1 . . H C5 .98999(3) -.01676(4) .38190(2) .00670(4) Uani d . 1 . . C C6 1.08821(3) -.18730(4) .46649(2) .00667(4) 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 .01595(8) .00875(7) .00538(7) -.00306(5) .00295(5) -.00055(5) O2 .01211(7) .00630(7) .00769(7) -.00365(4) .00263(5) .00007(5) O3 .01430(8) .00847(7) .00566(7) .00250(5) .00292(5) .00026(5) O4 .01214(7) .00651(7) .00835(7) .00341(4) .00257(5) -.00059(5) C1 .00846(8) .00568(7) .00551(7) -.00122(5) .00172(5) -.00042(5) C2 .00855(8) .00569(8) .00614(8) -.00173(5) .00160(5) -.00084(5) C3 .00780(8) .00514(7) .00639(7) -.00132(4) .00179(5) -.00024(5) C4 .00935(8) .00606(8) .00627(7) .00220(5) .00192(5) .00090(5) C5 .00854(8) .00576(7) .00570(7) .00117(5) .00176(5) .00032(5) C6 .00803(8) .00531(7) .00655(8) .00132(5) .00178(5) .00012(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 C1 . 1.3635(3) yes O1 H1 . .8400 n O2 C3 . 1.3710(3) yes O2 H3 . .8400 n O3 C5 . 1.3289(3) yes O3 H5 . .8400 n O4 C6 . 1.2386(3) yes C1 C2 . 1.3923(4) yes C1 C3 3_765 1.3994(4) yes C2 C3 . 1.3953(4) yes C2 H2 . .9500 n C3 C1 3_765 1.3994(4) yes C4 C5 . 1.3533(4) yes C4 C6 3_756 1.4423(4) yes C4 H4 . .9500 n C5 C6 . 1.5011(4) yes C6 C4 3_756 1.4423(4) yes loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0015 .0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0056 .0036 '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 C1 O1 H1 . . 109.5 ? C3 O2 H3 . . 109.5 ? C5 O3 H5 . . 109.5 ? O1 C1 C2 . . 124.09(2) yes O1 C1 C3 . 3_765 116.21(2) yes C2 C1 C3 . 3_765 119.69(2) yes C1 C2 C3 . . 119.76(2) yes C1 C2 H2 . . 120.1 ? C3 C2 H2 . . 120.1 ? O2 C3 C2 . . 122.87(2) yes O2 C3 C1 . 3_765 116.56(2) yes C2 C3 C1 . 3_765 120.55(2) yes C5 C4 C6 . 3_756 120.02(2) yes C5 C4 H4 . . 120.0 ? C6 C4 H4 3_756 . 120.0 ? O3 C5 C4 . . 126.27(2) yes O3 C5 C6 . . 112.78(2) yes C4 C5 C6 . . 120.94(2) yes O4 C6 C4 . 3_756 122.52(2) yes O4 C6 C5 . . 118.44(2) yes C4 C6 C5 3_756 . 119.04(2) yes 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 O1 H1 O4 3_755 .84 2.04 2.7316(4) 139.9 O2 H3 O4 4 .84 1.85 2.6816(4) 171.4 O3 H5 O2 . .84 1.95 2.7186(3) 151.9 _cod_database_fobs_code 2012015 _journal_paper_doi 10.1107/S0108270101003353