#------------------------------------------------------------------------------ #$Date: 2016-02-19 15:29:56 +0100 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/64/2006496.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_2006496 loop_ _publ_author_name 'Fitzgerald, Lawrence J.' 'Gerkin, Roger E.' _publ_section_title ; Benzophenone-3,3',4,4'-tetracarboxylic Acid Dihydrate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1267 _journal_page_last 1270 _journal_paper_doi 10.1107/S0108270197006069 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C17 H10 O9, 2H2 O' _chemical_formula_sum 'C17 H14 O11' _chemical_formula_weight 394.29 _chemical_name_common 'benzophenone-3,3',4,4'-tetracarboxylic acid dihydrate' _chemical_name_systematic ' ?' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _cell_angle_alpha 90 _cell_angle_beta 101.64(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.497(2) _cell_length_b 12.507(2) _cell_length_c 11.789(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 15.0 _cell_measurement_theta_min 14.7 _cell_volume 1660.3(5) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1989)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 296 _diffrn_measurement_device_type AFC5S _diffrn_measurement_method 2\q--\w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4182 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% '+- 1.8 (average maximum relative intensity)' _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'cut plate' _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.29 _refine_diff_density_min -0.22 _refine_ls_extinction_coef 7.0e-7(12) _refine_ls_extinction_method 'Zachariasen (1963, 1968)' _refine_ls_goodness_of_fit_ref 1.49 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 310 _refine_ls_number_reflns 3331 _refine_ls_R_factor_gt 0.054 _refine_ls_shift/su_max '< 0.01' _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/\s~F~^2^' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.049 _reflns_number_gt 3331 _reflns_number_total 3993 _reflns_threshold_expression 'I > 0.1\s(I)' _cod_data_source_file fr1049.cif _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 The following automatic conversions were performed: '_atom_site_adp_type' tag value 'Uij' was replaced with 'Uani' value 28 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 1/\s~F~^2^' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/\s~F~^2^'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1660.2(5) _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2006496 loop_ _symmetry_equiv_pos_as_xyz x,y,z '1/2 -x, 1/2 +y, -z' -x,-y,-z '1/2 +x, 1/2 -y, z' 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_calc_attached_atom O1 .18080(10) .17230(10) .86430(10) .0388(4) Uani ? ? O2 .09220(10) .03490(10) .93100(10) .0468(4) Uani ? ? O3 -.09610(10) -.11040(10) .79610(10) .0419(4) Uani ? ? O4 .06760(10) -.20280(10) .86530(10) .0466(4) Uani ? ? O6 .57970(10) .07270(10) .16000(10) .0447(4) Uani ? ? O5 .38960(10) .06730(10) .06940(10) .0411(4) Uani ? ? O8 .52970(10) -.15910(10) .10990(10) .0411(4) Uani ? ? O7 .58830(10) -.26510(10) .26200(10) .0394(4) Uani ? ? O9 .2596(2) .16520(10) .46770(10) .0494(5) Uani ? ? O10 -.19190(10) -.25300(10) .92090(10) .0364(4) Uani ? ? O11 .6723(2) -.3840(2) .1198(2) .0529(5) Uani ? ? C1 .1933(2) .0157(2) .5579(2) .0285(5) Uani ? ? C2 .1879(2) .0691(2) .6601(2) .0274(5) Uani ? ? C3 .1303(2) .02370(10) .74150(10) .0250(4) Uani ? ? C4 .0739(2) -.07500(10) .7176(2) .0272(5) Uani ? ? C5 .0754(2) -.1259(2) .6132(2) .0341(5) Uani ? ? C6 .1358(2) -.0816(2) .5342(2) .0347(5) Uani ? ? C7 .3345(2) .0019(2) .4126(2) .0288(5) Uani ? ? C8 .3701(2) .0478(2) .3173(2) .0296(5) Uani ? ? C9 .4382(2) -.00930(10) .25410(10) .0265(4) Uani ? ? C10 .4721(2) -.11440(10) .2856(2) .0280(5) Uani ? ? C11 .4398(2) -.1587(2) .3830(2) .0323(5) Uani ? ? C12 .3714(2) -.1010(2) .4466(2) .0335(5) Uani ? ? C13 .2615(2) .0687(2) .4777(2) .0313(5) Uani ? ? C14 .1322(2) .0762(2) .8554(2) .0282(5) Uani ? ? C15 .0161(2) -.1340(2) .8021(2) .0300(5) Uani ? ? C16 .4784(2) .04640(10) .1556(2) .0295(5) Uani ? ? C17 .5335(2) -.1807(2) .2105(2) .0296(5) Uani ? ? H2 .226(2) .134(2) .676(2) .035(6) Uiso ? ? H5 .038(2) -.194(2) .599(2) .038(6) Uiso ? ? H6 .140(2) -.120(2) .466(2) .047(6) Uiso ? ? H8 .345(2) .119(2) .292(2) .029(5) Uiso ? ? H11 .461(2) -.234(2) .403(2) .042(6) Uiso ? ? H12 .351(2) -.135(2) .512(2) .033(5) Uiso ? ? H3 .183(2) .200(2) .937(2) .071(8) Uiso ? ? H4 -.125(3) -.160(2) .847(3) .090(10) Uiso ? ? H9 .417(2) .097(2) .013(2) .069(8) Uiso ? ? H10 .621(3) -.305(3) .203(3) .100(10) Uiso ? ? H13 -.267(2) -.268(2) .895(2) .062(8) Uiso ? ? H14 -.150(3) -.312(3) .910(3) .090(10) Uiso ? ? H15 .635(6) -.381(5) .055(5) .23(3) Uiso ? ? H16 .665(5) -.442(4) .121(5) .18(3) Uiso ? ? 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 .0540(9) .0344(8) .0320(7) -.0115(7) .0179(7) -.0094(6) O2 .0640(10) .0472(9) .0353(8) -.0173(8) .0250(7) -.0052(7) O3 .0288(7) .0493(9) .0505(9) .0023(7) .0150(6) .0130(8) O4 .0386(8) .0444(9) .0596(10) .0065(7) .0169(7) .0229(8) O6 .0373(8) .0469(9) .0535(9) -.0032(7) .0181(7) .0177(7) O5 .0439(8) .0494(9) .0317(7) -.0011(7) .0116(7) .0125(7) O8 .0564(9) .0423(8) .0299(7) .0066(7) .0214(6) .0062(6) O7 .0487(9) .0363(8) .0349(7) .0124(7) .0128(7) .0043(6) O9 .0770(10) .0299(8) .0514(9) .0008(8) .0367(9) .0010(7) O10 .0314(8) .0352(8) .0449(8) -.0031(7) .0135(7) -.0100(7) O11 .0590(10) .0450(10) .0560(10) .0009(9) .0158(9) -.0152(9) C1 .0307(10) .0286(10) .0287(9) .0014(8) .0117(8) .0003(8) C2 .0285(9) .0252(10) .0301(9) -.0015(8) .0096(8) -.0014(8) C3 .0257(9) .0250(9) .0254(8) .0010(7) .0080(7) -.0011(7) C4 .0257(9) .0257(9) .0314(9) .0007(7) .0086(7) .0022(7) C5 .0400(10) .0290(10) .0360(10) -.0065(9) .0127(9) -.0053(8) C6 .0420(10) .0340(10) .0300(10) -.0029(9) .0134(8) -.0080(8) C7 .0322(10) .0294(10) .0268(9) -.0018(8) .0103(7) -.0009(8) C8 .0334(10) .0274(10) .0294(9) -.0018(8) .0099(8) .0022(8) C9 .0288(9) .0281(9) .0239(8) -.0038(8) .0083(7) .0014(7) C10 .0294(9) .0294(10) .0262(9) -.0008(8) .0080(7) .0017(8) C11 .0400(10) .0300(10) .0288(10) .0027(9) .0123(8) .0063(8) C12 .0420(10) .0340(10) .0286(9) -.0002(9) .0163(8) .0067(8) C13 .0380(10) .0320(10) .0267(9) -.0004(9) .0125(8) -.0002(8) C14 .0285(9) .0300(10) .0276(9) -.0003(8) .0092(7) -.0006(8) C15 .0290(9) .0287(10) .0339(10) -.0035(8) .0098(8) -.0019(8) C16 .0370(10) .0256(9) .0288(9) .0032(8) .0140(8) .0037(8) C17 .0311(10) .0273(10) .0325(10) -.0022(8) .0111(8) .0019(8) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart, Davidson & Simpson (1965)' C .002 .002 'Cromer & Waber (1974)' O .008 .006 'Cromer & Waber (1974)' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C14 O1 H3 110.0(10) no C15 O3 H4 105.0(10) no C16 O5 H9 109.0(10) no C17 O7 H10 106.0(10) no H13 O10 H14 106(2) no H15 O11 H16 91(4) no C2 C1 C6 119.6(2) no C2 C1 C13 117.1(2) no C6 C1 C13 123.3(2) no C1 C2 C3 120.9(2) no C1 C2 H2 119.0(10) no C3 C2 H2 119.0(10) no C2 C3 C4 119.2(2) no C2 C3 C14 121.2(2) no C4 C3 C14 119.6(2) no C3 C4 C5 119.7(2) no C3 C4 C15 123.5(2) no C5 C4 C15 116.7(2) no C4 C5 C6 120.7(2) no C4 C5 H5 118.0(10) no C6 C5 H5 120.0(10) no C1 C6 C5 119.9(2) no C1 C6 H6 120.0(10) no C5 C6 H6 119.0(10) no C8 C7 C12 119.4(2) no C8 C7 C13 117.9(2) no C12 C7 C13 122.6(2) no C7 C8 C9 120.8(2) no C7 C8 H8 120.0(10) no C9 C8 H8 118.0(10) no C8 C9 C10 119.9(2) no C8 C9 C16 118.2(2) no C10 C9 C16 121.8(2) no C9 C10 C11 119.1(2) no C9 C10 C17 120.2(2) no C11 C10 C17 120.5(2) no C10 C11 C12 120.8(2) no C10 C11 H11 118.0(10) no C12 C11 H11 120.0(10) no C7 C12 C11 119.9(2) no C7 C12 H12 122.0(10) no C11 C12 H12 117.0(10) no O9 C13 C1 120.0(2) yes O9 C13 C7 120.4(2) yes C1 C13 C7 119.6(2) yes O1 C14 O2 123.5(2) yes O1 C14 C3 113.70(10) yes O2 C14 C3 122.7(2) yes O3 C15 O4 123.2(2) yes O3 C15 C4 114.6(2) yes O4 C15 C4 122.0(2) yes O5 C16 C9 112.2(2) yes O6 C16 O5 125.1(2) yes O6 C16 C9 122.6(2) yes O7 C17 C10 114.3(2) yes O8 C17 O7 123.5(2) yes O8 C17 C10 122.1(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C14 ? ? 1.320(2) yes O1 H3 ? ? .92(3) no O2 C14 ? ? 1.201(2) yes O3 C15 ? ? 1.311(2) yes O3 H4 ? ? .96(3) no O4 C15 ? ? 1.211(2) yes O5 C16 ? ? 1.312(2) yes O5 H9 ? ? .88(3) no O6 C16 ? ? 1.201(2) yes O7 C17 ? ? 1.314(2) yes O7 H10 ? ? .99(3) no O8 C17 ? ? 1.209(2) yes O9 C13 ? ? 1.212(2) no O10 H13 ? ? .87(3) no O10 H14 ? ? .91(3) no O11 H15 ? ? .79(6) no O11 H16 ? ? .74(5) no C1 C2 ? ? 1.390(2) no C1 C6 ? ? 1.387(3) no C1 C13 ? ? 1.499(2) no C2 C3 ? ? 1.392(2) no C2 H2 ? ? .92(2) no C3 C4 ? ? 1.396(2) no C3 C14 ? ? 1.490(2) no C4 C5 ? ? 1.389(3) no C4 C15 ? ? 1.499(2) no C5 C6 ? ? 1.385(3) no C5 H5 ? ? .96(2) no C6 H6 ? ? .95(2) no C7 C8 ? ? 1.394(2) no C7 C12 ? ? 1.389(3) no C7 C13 ? ? 1.501(2) no C8 C9 ? ? 1.384(2) no C8 H8 ? ? .96(2) no C9 C10 ? ? 1.400(2) no C9 C16 ? ? 1.505(2) no C10 C11 ? ? 1.390(2) no C10 C17 ? ? 1.490(2) no C11 C12 ? ? 1.392(3) no C11 H11 ? ? .99(2) no C12 H12 ? ? .95(2) no 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 O1 H3 O10 3_557 0.92(3) 1.78(3) 2.705(2) 179(2) yes O1 H3 O8 2_556 0.92(3) 2.98(3) 3.270(2) 100(2) yes O1 H3 O11 3_656 0.92(3) 3.00(3) 3.126(2) 89(2) yes O3 H4 O10 ? 0.96(3) 1.73(3) 2.686(2) 172(3) yes O5 H9 O8 3_655 0.88(3) 1.85(3) 2.727(2) 178(3) yes O5 H9 O4 2_556 0.88(3) 2.88(3) 2.992(2) 89(2) yes O5 H9 O6 3_655 0.88(3) 2.94(3) 3.300(2) 106(2) yes O7 H10 O11 ? 0.99(3) 1.59(3) 2.571(2) 171(3) yes O10 H13 O4 4_445 0.87(3) 1.90(3) 2.766(2) 170(2) yes O10 H13 O5 3_556 0.87(3) 2.96(3) 3.268(2) 103(2) yes O10 H14 O6 2_546 0.91(3) 1.92(3) 2.797(2) 163(3) yes O10 H14 O8 4_446 0.91(3) 2.83(3) 3.220(2) 108(2) yes O10 H14 O4 ? 0.91(3) 2.99(3) 3.243(2) 98(2) yes O11 H15 O2 4_544 0.79(6) 2.41(7) 2.921(2) 123(6) yes O11 H15 O4 4_544 0.79(6) 2.45(6) 3.189(3) 155(6) yes O11 H15 O2 2_546 0.79(6) 2.85(6) 3.146(3) 105(5) yes O11 H16 O2 4_544 0.74(5) 2.51(5) 2.921(2) 118(5) yes O11 H16 O3 2_546 0.74(5) 2.51(5) 3.181(3) 152(5) yes O11 H16 O2 2_546 0.74(5) 2.91(5) 3.146(2) 102(5) yes