#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/20/2012014.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_2012014 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 105.78(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.387(3) _cell_length_b 6.0600(10) _cell_length_c 12.198(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 163(2) _cell_measurement_theta_max 38.86 _cell_measurement_theta_min 30.84 _cell_volume 525.5(3) _computing_cell_refinement 'DIRAX (Duisenberg, 1992)' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1993)' _computing_data_reduction 'local programs' _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 163(3) _diffrn_measured_fraction_theta_full .998 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'standard-focus sealed tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .021 _diffrn_reflns_av_sigmaI/netI .016 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 3379 _diffrn_reflns_theta_full 62.97 _diffrn_reflns_theta_max 62.97 _diffrn_reflns_theta_min 6.34 _diffrn_standards_decay_% <2 _diffrn_standards_interval_count 100 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 1.339 _exptl_absorpt_correction_T_max .938 _exptl_absorpt_correction_T_min .877 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details 'face-indexed (de Meulenaer & Tompa, 1965)' _exptl_crystal_colour black _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 292 _exptl_crystal_size_max .43 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .05 _refine_diff_density_max .19 _refine_diff_density_min -.25 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.14 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 94 _refine_ls_number_reflns 842 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.14 _refine_ls_R_factor_all .038 _refine_ls_R_factor_gt .035 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0694P)^2^+0.1389P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .114 _reflns_number_gt 753 _reflns_number_total 842 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file da1173.cif _[local]_cod_data_source_block IIa _[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_original_cell_volume 525.4(3) _cod_database_code 2012014 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 .98007(14) .55646(16) -.22730(7) .0146(4) Uani d . 1 . . O H1 .9384 .4434 -.2657 .017 Uiso calc R 1 . . H O2 .82695(13) .15885(16) .08177(7) .0131(4) Uani d . 1 . . O H3 .7812 .0663 .0305 .016 Uiso calc R 1 . . H O3 .99530(13) -.06305(16) .27657(7) .0140(4) Uani d . 1 . . O H5 .9471 .0412 .2329 .017 Uiso calc R 1 . . H O4 1.16048(13) -.34700(15) .43160(7) .0133(4) Uani d . 1 . . O C1 .98734(18) .5200(2) -.11557(11) .0106(4) Uani d . 1 . . C C2 .90043(19) .3446(2) -.07742(11) .0114(4) Uani d . 1 . . C H2 .8324 .2384 -.1299 .014 Uiso calc R 1 . . H C3 .91311(18) .3248(2) .03786(11) .0112(4) Uani d . 1 . . C C4 .90720(19) .1594(2) .41533(11) .0116(4) Uani d . 1 . . C H4 .8454 .2656 .3606 .014 Uiso calc R 1 . . H C5 .98966(18) -.0161(2) .38227(11) .0111(4) Uani d . 1 . . C C6 1.08814(18) -.1877(2) .46676(11) .0114(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 .0228(6) .0131(6) .0076(6) -.0044(4) .0037(4) -.0018(4) O2 .0179(6) .0105(6) .0107(5) -.0049(4) .0038(4) -.0010(4) O3 .0209(6) .0131(6) .0078(6) .0041(4) .0036(4) .0013(4) O4 .0161(6) .0111(6) .0127(6) .0029(4) .0040(4) -.0010(4) C1 .0116(7) .0107(7) .0095(7) .0026(5) .0030(5) .0004(5) C2 .0105(7) .0116(8) .0112(7) .0002(5) .0013(5) -.0026(5) C3 .0099(7) .0093(8) .0146(7) .0013(5) .0035(6) .0013(5) C4 .0109(7) .0114(8) .0115(7) .0001(5) .0011(5) .0027(5) C5 .0113(7) .0116(7) .0100(7) -.0028(5) .0024(5) -.0001(5) C6 .0088(7) .0104(8) .0148(8) -.0027(5) .0029(6) -.0008(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 . 1.3671(16) yes O1 H1 . .8400 n O2 C3 . 1.3742(17) yes O2 H3 . .8400 n O3 C5 . 1.3320(16) yes O3 H5 . .8400 n O4 C6 . 1.2355(17) yes C1 C2 . 1.386(2) yes C1 C3 3_765 1.394(2) yes C2 C3 . 1.3887(19) yes C2 H2 . .9500 n C3 C1 3_765 1.394(2) yes C4 C5 . 1.341(2) yes C4 C6 3_756 1.4395(19) yes C4 H4 . .9500 n C5 C6 . 1.505(2) yes C6 C4 3_756 1.4395(19) yes loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 '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 .0492 .0322 '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 . . 124.22(12) yes O1 C1 C3 . 3_765 116.06(12) yes C2 C1 C3 . 3_765 119.71(13) yes C1 C2 C3 . . 119.77(12) yes C1 C2 H2 . . 120.1 ? C3 C2 H2 . . 120.1 ? O2 C3 C2 . . 123.18(12) yes O2 C3 C1 . 3_765 116.29(12) yes C2 C3 C1 . 3_765 120.52(12) yes C5 C4 C6 . 3_756 120.36(12) yes C5 C4 H4 . . 119.8 ? C6 C4 H4 3_756 . 119.8 ? O3 C5 C4 . . 126.65(13) yes O3 C5 C6 . . 112.26(12) yes C4 C5 C6 . . 121.10(13) yes O4 C6 C4 . 3_756 123.02(12) yes O4 C6 C5 . . 118.44(12) yes C4 C6 C5 3_756 . 118.54(12) 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 2.7370(10) 139.9 O2 H3 O4 4 .84 1.85 2.686(2) 171.6 O3 H5 O2 . .84 1.95 2.7190(10) 151.5 _cod_database_fobs_code 2012014