#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/20/2012013.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_2012013 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_paper_doi 10.1107/S0108270101003353 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C6 H6 O4 , H2 O' _chemical_formula_sum 'C6 H8 O5' _chemical_formula_weight 160.12 _chemical_melting_point 490.5(5) _chemical_name_systematic ; 1,2,4,5-Tetrahydroxybenzene monohydrate ; _space_group_IT_number 13 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yac' _symmetry_space_group_name_H-M 'P 1 2/n 1' _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 102.33(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.487(3) _cell_length_b 3.6470(10) _cell_length_c 13.506(3) _cell_measurement_reflns_used 623 _cell_measurement_temperature 203(2) _cell_measurement_theta_max 28.30 _cell_measurement_theta_min 1.94 _cell_volume 649.0(3) _computing_cell_refinement 'SMART (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT-Plus (Bruker, 1998)' _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 203(2) _diffrn_measured_fraction_theta_full .977 _diffrn_measured_fraction_theta_max .977 _diffrn_measurement_device_type 'Bruker Smart1000 CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'standard-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .022 _diffrn_reflns_av_sigmaI/netI .029 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3708 _diffrn_reflns_theta_full 28.30 _diffrn_reflns_theta_max 28.30 _diffrn_reflns_theta_min 1.94 _diffrn_standards_decay_% <2 _exptl_absorpt_coefficient_mu .146 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale pink' _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 336 _exptl_crystal_size_max .5 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _refine_diff_density_max .39 _refine_diff_density_min -.26 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.22 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 116 _refine_ls_number_reflns 1578 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.22 _refine_ls_R_factor_all .055 _refine_ls_R_factor_gt .045 _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^)+(0.036P)^2^+1.0778P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .149 _reflns_number_gt 1270 _reflns_number_total 1578 _reflns_threshold_expression I>2\s(I) _cod_data_source_file da1173.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '490-491' was changed to '490.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '490-491' was changed to '490.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 649.1(2) _cod_original_sg_symbol_H-M 'P 2/n' _cod_database_code 2012013 _cod_database_fobs_code 2012013 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, 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 0.20737(11) .4354(5) 0.57575(12) .0246(4) Uani d . 1 . . O H1 0.2390 .4655 0.5300 .033(8) Uiso calc R 1 . . H O2 0.07215(12) .2709(5) 0.69800(12) .0258(4) Uani d . 1 . . O H2 0.1271 .1621 0.7036 .069(13) Uiso calc R 1 . . H O3 -0.07741(11) 1.1076(5) 0.79534(11) .0230(4) Uani d . 1 . . O H3A -0.0308 1.1273 0.7643 .042(9) Uiso calc R 1 . . H O4 0.19309(11) .7111(5) 1.06635(12) .0225(4) Uani d . 1 . . O H4 0.1986 .6191 1.1235 .044(10) Uiso calc R 1 . . H O5 0.25 .3507(7) 0.25 .0243(5) Uani d S 1 . . O H5A 0.298(2) .221(11) 0.250(3) .051(11) Uiso d . 1 . . H O6 0.25 .8880(8) 0.75 .0261(5) Uani d S 1 . . O H6A 0.251(4) .738(16) 0.692(3) .102(18) Uiso d . 1 . . H C1 0.10420(16) .4680(6) 0.53592(16) .0190(5) Uani d . 1 . . C C2 0.03826(16) .3815(6) 0.59895(16) .0188(5) Uani d . 1 . . C C3 -0.06586(16) .4139(6) 0.56214(16) .0199(5) Uani d . 1 . . C H3B -0.1107 .3549 0.6043 .019(6) Uiso calc R 1 . . H C4 -0.03683(16) 1.0535(6) 0.89710(16) .0176(4) Uani d . 1 . . C C5 0.05936(16) .9069(6) 0.93179(16) .0186(5) Uani d . 1 . . C H5B 0.0993 .8431 0.8853 .019(6) Uiso calc R 1 . . H C6 0.09686(15) .8541(6) 1.03462(16) .0180(5) 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 .0151(7) .0399(10) .0192(8) -.0018(7) .0047(6) .0044(7) O2 .0193(8) .0400(10) .0187(8) .0036(7) .0055(6) .0094(7) O3 .0171(7) .0380(10) .0144(8) .0021(7) .0048(6) .0043(7) O4 .0162(7) .0336(9) .0185(8) .0060(7) .0056(6) .0038(7) O5 .0187(11) .0305(13) .0232(12) 0 .0031(9) 0 O6 .0215(11) .0355(14) .0210(12) 0 .0037(9) 0 C1 .0150(9) .0230(11) .0194(10) -.0008(8) .0045(8) .0008(9) C2 .0189(10) .0216(11) .0158(10) -.0011(8) .0036(8) .0016(8) C3 .0179(10) .0255(12) .0178(11) -.0017(9) .0074(8) .0030(9) C4 .0170(10) .0218(11) .0144(9) -.0012(8) .0045(8) .0012(8) C5 .0166(10) .0229(11) .0182(10) .0007(8) .0082(8) -.0004(8) C6 .0144(9) .0195(10) .0202(11) .0002(8) .0042(8) .0012(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 '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 .0106 .0060 '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' 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 ? C2 O2 H2 . . 109.5 ? C4 O3 H3A . . 109.5 ? C6 O4 H4 . . 109.5 ? H5A O5 H5A 2 . 107(6) ? H6A O6 H6A . 2_556 110(7) ? C3 C1 O1 3_566 . 122.50(19) yes C3 C1 C2 3_566 . 119.9(2) yes O1 C1 C2 . . 117.57(19) yes O2 C2 C3 . . 118.15(19) yes O2 C2 C1 . . 122.5(2) yes C3 C2 C1 . . 119.4(2) yes C1 C3 C2 3_566 . 120.7(2) yes C1 C3 H3B 3_566 . 119.6 ? C2 C3 H3B . . 119.6 ? O3 C4 C5 . . 122.27(19) yes O3 C4 C6 . 3_577 117.50(19) yes C5 C4 C6 . 3_577 120.2(2) yes C6 C5 C4 . . 120.41(19) yes C6 C5 H5B . . 119.8 ? C4 C5 H5B . . 119.8 ? O4 C6 C5 . . 118.79(19) yes O4 C6 C4 . 3_577 121.84(19) yes C5 C6 C4 . 3_577 119.4(2) yes 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 . 1.386(2) yes O1 H1 . .8300 n O2 C2 . 1.378(3) yes O2 H2 . .8300 n O3 C4 . 1.381(3) yes O3 H3A . .8300 n O4 C6 . 1.379(3) yes O4 H4 . .8300 n O5 H5A 2 .80(4) yes O5 H5A . .80(4) yes O6 H6A . .95(5) yes O6 H6A 2_556 .95(5) yes C1 C3 3_566 1.384(3) yes C1 C2 . 1.392(3) yes C2 C3 . 1.391(3) yes C3 C1 3_566 1.384(3) yes C3 H3B . .9400 n C4 C5 . 1.389(3) yes C4 C6 3_577 1.392(3) yes C5 C6 . 1.386(3) yes C5 H5B . .9400 n C6 C4 3_577 1.392(3) 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 2_556 .83 1.96 2.756(2) 160.4 O2 H2 O6 1_545 .83 1.92 2.735(2) 165.8 O3 H3A O2 1_565 .83 1.88 2.699(2) 168.8 O4 H4 O5 1_556 .83 1.96 2.767(2) 162.9 O5 H5A O3 4_665 .77(3) 2.07(3) 2.826(2) 165(3) O6 H6A O1 . .95(5) 1.91(5) 2.832(2) 162(3)