#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/84/2018453.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_2018453 loop_ _publ_author_name 'Landre, I. M. R.' 'Martins, F. T.' 'Ellena, J. A.' 'Dos Santos, M. H.' 'Doriguetto, A. C.' _publ_section_title ; Pseudopolymorphism in hydroxybenzophenones: the dihydrate of 2,2',4,4'-tetrahydroxybenzophenone ; _journal_coeditor_code FA3271 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o156 _journal_page_last o159 _journal_volume 68 _journal_year 2012 _chemical_formula_iupac 'C13 H10 O5 , 2H2 O' _chemical_formula_moiety 'C13 H10 O5, 2(H2 O)' _chemical_formula_sum 'C13 H14 O7' _chemical_formula_weight 282.24 _chemical_name_common ; 2,2',4,4'-tetrahydroxybenzophenone dihydrate ; _chemical_name_systematic ; bis(2,4-dihydroxyphenyl)methanone 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 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 100.628(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.1394(4) _cell_length_b 7.7629(3) _cell_length_c 11.0690(4) _cell_measurement_reflns_used 7662 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 26.022 _cell_measurement_theta_min 2.91 _cell_volume 1278.58(8) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 295 _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7103 _diffrn_reflns_theta_full 26.04 _diffrn_reflns_theta_max 26.04 _diffrn_reflns_theta_min 3.36 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.137 _refine_diff_density_min -0.152 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 1240 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0428 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0728P)^2^+0.4275P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.126 _reflns_number_gt 981 _reflns_number_total 1240 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 2244bzf in C 2/c CELL 0.71073 15.1394 7.7629 11.0690 90.000 100.628 90.000 ZERR 4.00 0.0004 0.0003 0.0004 0.000 0.002 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H O UNIT 52 56 28 MERG 2 omit 1 1 0 omit 1 1 1 MPLA 6 C1 C6 C5 C4 C5 C6 C7 O1 O2 O3 FMAP 2 PLAN 8 ACTA BOND $H CONF L.S. 10 WGHT 0.072800 0.427500 FVAR 0.59649 MOLE 1 C1 1 0.448147 0.488646 0.144272 11.00000 0.03611 0.03692 = 0.03244 0.00062 0.00084 0.00134 C2 1 0.379799 0.575683 0.062707 11.00000 0.04052 0.03346 = 0.03690 0.00264 0.00441 0.00404 C3 1 0.327716 0.491447 -0.034768 11.00000 0.03937 0.03924 = 0.03766 0.00344 -0.00378 0.00506 AFIX 43 H3 2 0.280959 0.549406 -0.084724 11.00000 -1.20000 AFIX 0 C4 1 0.344778 0.321279 -0.058429 11.00000 0.03943 0.03868 = 0.03235 0.00156 -0.00028 -0.00222 C5 1 0.416086 0.235205 0.014977 11.00000 0.04525 0.03558 = 0.03827 -0.00109 -0.00028 0.00498 AFIX 43 H5 2 0.429592 0.122231 -0.002876 11.00000 -1.20000 AFIX 0 C6 1 0.465815 0.318328 0.113190 11.00000 0.03832 0.04016 = 0.03707 0.00187 -0.00163 0.00633 AFIX 43 H6 2 0.513247 0.259888 0.161402 11.00000 -1.20000 AFIX 0 C7 1 0.500000 0.579492 0.250000 10.50000 0.03922 0.03632 = 0.03601 0.00000 0.00433 0.00000 O1 3 0.500000 0.741812 0.250000 10.50000 0.05683 0.03625 = 0.04234 0.00000 -0.00478 0.00000 O2 3 0.362299 0.745705 0.077272 11.00000 0.05731 0.03601 = 0.04650 -0.00212 -0.00875 0.01030 O3 3 0.292505 0.244246 -0.155368 11.00000 0.05556 0.03976 = 0.04188 -0.00206 -0.01377 0.00073 H2A 2 0.408732 0.785033 0.138649 11.00000 -1.50000 H3A 2 0.304714 0.132924 -0.156069 11.00000 -1.50000 MOLE 2 AFIX 6 O4 3 0.331765 -0.085537 -0.166048 11.00000 0.06505 0.04204 = 0.05065 -0.00273 -0.01053 -0.00154 AFIX 5 H4A 2 0.332050 -0.127039 -0.097088 11.00000 -1.50000 H4B 2 0.300714 -0.143079 -0.224952 11.00000 -1.50000 HKLF 4 REM 2244bzf in C 2/c REM R1 = 0.0428 for 981 Fo > 4sig(Fo) and 0.0541 for all 1240 data REM 101 parameters refined using 0 restraints END WGHT 0.0734 0.3956 REM Highest difference peak 0.137, deepest hole -0.152, 1-sigma level 0.035 Q1 1 0.4291 0.5308 0.1025 11.00000 0.05 0.14 Q2 1 0.3583 0.2690 -0.0096 11.00000 0.05 0.13 Q3 1 0.4640 0.5177 0.1802 11.00000 0.05 0.13 Q4 1 0.4618 0.4240 0.1215 11.00000 0.05 0.12 Q5 1 0.3328 0.3855 -0.0382 11.00000 0.05 0.11 Q6 1 0.5437 0.2796 0.1328 11.00000 0.05 0.11 Q7 1 0.3116 0.2788 -0.0851 11.00000 0.05 0.10 Q8 1 0.3416 0.5193 0.0351 11.00000 0.05 0.10 ; _[local]_cod_data_source_file fa3271.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_original_cell_volume 1278.57(8) _cod_database_code 2018453 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_type_symbol _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 C C1 0.44815(8) 0.48865(19) 0.14427(12) 0.0359(4) Uani d . 1 C C2 0.37980(9) 0.57568(18) 0.06271(13) 0.0373(4) Uani d . 1 C C3 0.32772(9) 0.49145(19) -0.03477(12) 0.0401(4) Uani d . 1 H H3 0.281 0.5494 -0.0847 0.048 Uiso calc R 1 C C4 0.34478(9) 0.32128(19) -0.05843(12) 0.0377(4) Uani d . 1 C C5 0.41609(10) 0.23521(19) 0.01498(13) 0.0407(4) Uani d . 1 H H5 0.4296 0.1222 -0.0029 0.049 Uiso calc R 1 C C6 0.46581(9) 0.31833(19) 0.11319(13) 0.0396(4) Uani d . 1 H H6 0.5132 0.2599 0.1614 0.048 Uiso calc R 1 C C7 0.5 0.5795(3) 0.25 0.0375(5) Uani d S 1 O O1 0.5 0.74181(18) 0.25 0.0469(4) Uani d S 1 O O2 0.36230(8) 0.74570(14) 0.07727(11) 0.0489(4) Uani d . 1 O O3 0.29250(8) 0.24425(15) -0.15537(10) 0.0486(3) Uani d . 1 H H2A 0.4087(16) 0.785(3) 0.139(2) 0.073 Uiso d . 1 H H3A 0.3047(14) 0.133(3) -0.1561(19) 0.073 Uiso d . 1 O O4 0.33177(8) -0.08554(14) -0.16605(11) 0.0553(4) Uani d G 1 H H4A 0.3321 -0.127 -0.0971 0.083 Uiso d G 1 H H4B 0.3007 -0.1431 -0.225 0.083 Uiso d G 1 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 C1 0.0361(7) 0.0369(8) 0.0324(7) 0.0013(5) 0.0008(6) 0.0006(5) C2 0.0405(7) 0.0335(8) 0.0369(7) 0.0040(5) 0.0044(6) 0.0026(5) C3 0.0394(7) 0.0392(8) 0.0377(8) 0.0051(6) -0.0038(6) 0.0034(6) C4 0.0394(7) 0.0387(8) 0.0324(7) -0.0022(6) -0.0003(5) 0.0016(6) C5 0.0453(8) 0.0356(8) 0.0383(7) 0.0050(6) -0.0003(6) -0.0011(6) C6 0.0383(7) 0.0402(8) 0.0371(7) 0.0063(6) -0.0016(6) 0.0019(6) C7 0.0392(10) 0.0363(11) 0.0360(10) 0 0.0043(8) 0 O1 0.0568(9) 0.0363(8) 0.0423(8) 0 -0.0048(7) 0 O2 0.0573(7) 0.0360(6) 0.0465(6) 0.0103(5) -0.0087(5) -0.0021(4) O3 0.0556(7) 0.0398(6) 0.0419(6) 0.0007(5) -0.0138(5) -0.0021(5) O4 0.0650(8) 0.0420(7) 0.0507(7) -0.0015(5) -0.0105(6) -0.0027(5) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 ' 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 C6 C1 C2 . . 116.34(12) C6 C1 C7 . . 123.43(12) C2 C1 C7 . . 120.11(14) O2 C2 C3 . . 117.18(12) O2 C2 C1 . . 121.55(13) C3 C2 C1 . . 121.26(13) C2 C3 C4 . . 120.17(12) C2 C3 H3 . . 119.9 C4 C3 H3 . . 119.9 O3 C4 C3 . . 118.16(12) O3 C4 C5 . . 121.85(14) C3 C4 C5 . . 119.96(13) C6 C5 C4 . . 119.41(14) C6 C5 H5 . . 120.3 C4 C5 H5 . . 120.3 C5 C6 C1 . . 122.56(12) C5 C6 H6 . . 118.7 C1 C6 H6 . . 118.7 O1 C7 C1 . 2_655 118.79(9) O1 C7 C1 . . 118.79(9) C1 C7 C1 2_655 . 122.42(18) C2 O2 H2A . . 105.4(13) C4 O3 H3A . . 110.3(14) H4A O4 H4B . . 114.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance C1 C6 . 1.404(2) C1 C2 . 1.4134(19) C1 C7 . 1.4644(16) C2 O2 . 1.3616(17) C2 C3 . 1.378(2) C3 C4 . 1.380(2) C3 H3 . 0.93 C4 O3 . 1.3498(17) C4 C5 . 1.396(2) C5 C6 . 1.365(2) C5 H5 . 0.93 C6 H6 . 0.93 C7 O1 . 1.260(2) C7 C1 2_655 1.4644(16) O2 H2A . 0.93(3) O3 H3A . 0.88(2) O4 H4A . 0.8278 O4 H4B . 0.8559 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 _geom_hbond_publ_flag O2 H2A O1 . 0.94(2) 1.71(2) 2.5560(10) 150(2) yes O3 H3A O4 . 0.88(2) 1.75(2) 2.636(2) 176(2) yes O4 H4A O2 1_545 0.83 2.14 2.954(2) 167 yes O4 H4B O3 4_544 0.86 1.95 2.797(2) 167 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion C6 C1 C2 O2 . -174.01(13) C7 C1 C2 O2 . 2.2(2) C6 C1 C2 C3 . 6.3(2) C7 C1 C2 C3 . -177.48(11) O2 C2 C3 C4 . 176.80(13) C1 C2 C3 C4 . -3.5(2) C2 C3 C4 O3 . -179.53(13) C2 C3 C4 C5 . -1.3(2) O3 C4 C5 C6 . -178.86(14) C3 C4 C5 C6 . 3.0(2) C4 C5 C6 C1 . 0.1(2) C2 C1 C6 C5 . -4.6(2) C7 C1 C6 C5 . 179.28(13) C6 C1 C7 O1 . 157.60(11) C2 C1 C7 O1 . -18.33(14) C6 C1 C7 C1 2_655 -22.40(11) C2 C1 C7 C1 2_655 161.67(14) _cod_database_fobs_code 2018453