#------------------------------------------------------------------------------ #$Date: 2013-02-21 15:50:38 +0200 (Thu, 21 Feb 2013) $ #$Revision: 73908 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/73/4507313.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4507313 loop_ _publ_author_name 'Braun, Doris E.' 'Bhardwaj, Rajni M.' 'Florence, Alastair J.' 'Tocher, Derek A.' 'Price, Sarah L.' _publ_section_title ; Complex Polymorphic System of Gallic Acid-Five Monohydrates, Three Anhydrates, and over 20 Solvates. ; _journal_issue 1 _journal_name_full 'Crystal growth & design' _journal_page_first 19 _journal_page_last 23 _journal_volume 13 _journal_year 2013 _chemical_formula_moiety 'C7 H6 O5' _chemical_formula_sum 'C7 H6 O5' _chemical_formula_weight 170.12 _chemical_name_common 'gallic acid' _chemical_name_systematic ; 3,4,5-trihydroxybenzoic acid ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 102.1116(17) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.2303(1) _cell_length_b 5.26495(12) _cell_length_c 24.7927(4) _cell_measurement_temperature 298 _cell_volume 667.53(2) _diffrn_ambient_temperature 298 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54056 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.693 _pd_proc_ls_prof_R_factor 0.026 _pd_proc_ls_prof_wR_expected 0.015 _pd_proc_ls_prof_wR_factor 0.031 _refine_ls_goodness_of_fit_all 2.065 _[local]_cod_data_source_file cg301506x_si_002.cif _[local]_cod_data_source_block gallic_acid_anhdyrate_III _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius ; _cod_database_code 4507313 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv O9 O Uiso 0.7295(9) 0.7458(13) 0.01674(18) 1.000 0.0228 O10 O Uiso 0.4165(10) 0.8860(11) 0.0544(3) 1.000 0.0228 O11 O Uiso 0.5279(8) 0.3461(7) 0.22904(17) 1.000 0.0228 O13 O Uiso 1.1290(9) 0.0017(8) 0.13598(17) 1.000 0.0228 O16 O Uiso 0.9070(8) 0.0023(9) 0.22204(16) 1.000 0.0228 C1 C Uiso 0.6736(7) 0.5381(7) 0.09806(14) 1.000 0.0228 C2 C Uiso 0.5590(7) 0.5342(7) 0.14255(14) 1.000 0.0228 C3 C Uiso 0.8633(6) 0.3675(6) 0.09350(14) 1.000 0.0228 C4 C Uiso 0.5851(8) 0.7349(8) 0.05490(16) 1.000 0.0228 C6 C Uiso 0.6381(7) 0.3525(6) 0.18447(14) 1.000 0.0228 C7 C Uiso 0.9453(5) 0.1848(6) 0.13441(13) 1.000 0.0228 C12 C Uiso 0.8319(6) 0.1773(6) 0.18025(14) 1.000 0.0228 H5 H Uiso 0.426(4) 0.654(4) 0.1436(7) 1.000 0.0274 H8 H Uiso 0.932(3) 0.380(4) 0.0622(7) 1.000 0.0274 H14 H Uiso 0.639(3) 0.847(4) -0.0108(7) 1.000 0.0274 H15 H Uiso 0.598(4) 0.222(4) 0.2520(6) 1.000 0.0274 H17 H Uiso 1.196(4) 0.013(4) 0.1064(7) 1.000 0.0274 H18 H Uiso 1.031(4) -0.095(4) 0.2140(9) 1.000 0.0274 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 C4 O9 H14 105.9(11) no C6 O11 H15 110.6(13) no C7 O13 H17 109.4(14) no C12 O16 H18 109.0(15) no C2 C1 C3 120.7(3) no C2 C1 C4 117.9(3) no C3 C1 C4 121.4(3) no C1 C2 C6 119.8(3) no C1 C3 C7 120.8(3) no O9 C4 C1 113.8(4) yes O10 C4 C1 126.3(5) yes O9 C4 O10 119.7(5) yes O11 C6 C2 120.7(3) yes O11 C6 C12 119.2(3) yes C2 C6 C12 120.0(3) no O13 C7 C3 128.1(3) yes O13 C7 C12 112.2(3) yes C3 C7 C12 119.6(3) no O16 C12 C7 122.0(3) yes C6 C12 C7 119.1(3) no O16 C12 C6 118.9(3) yes C1 C2 H5 117.7(11) no C6 C2 H5 122.5(11) no C1 C3 H8 116.2(12) no C7 C3 H8 123.0(12) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O9 C4 1.330(6) yes O10 C4 1.186(7) yes O11 C6 1.350(5) yes O13 C7 1.356(5) yes O16 C12 1.381(5) yes O9 H14 0.916(19) no O11 H15 0.893(19) no O13 H17 0.879(19) no O16 H18 0.88(2) no C1 C2 1.362(5) no C1 C3 1.361(5) no C1 C4 1.492(5) no C2 C6 1.409(5) no C3 C7 1.398(5) no C6 C12 1.391(5) no C7 C12 1.389(4) no C2 H5 0.94(2) no C3 H8 0.923(17) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O9 O10 2.624(9) 3_675 no O9 C4 3.323(7) 3_665 no O10 O9 2.624(9) 3_675 no O10 C4 3.364(8) 3_675 no O10 O13 2.828(8) 1_465 no O10 O10 3.236(10) 3_675 no O11 O11 2.868(5) 2_655 no O11 O16 3.063(6) 2_755 no O11 O11 2.868(5) 2_645 no O11 O16 2.717(6) . no O11 O16 2.912(6) 2_655 no O13 O10 2.828(8) 1_645 no O13 C2 3.315(6) 1_645 no O13 C1 3.402(6) 1_545 no O13 O16 2.635(6) . no O13 C6 3.256(6) 1_655 no O16 O11 2.717(6) . no O16 C6 3.056(5) 2_745 no O16 C12 3.045(5) 2_745 no O16 O16 3.039(6) 2_745 no O16 O13 2.635(6) . no O16 O11 2.912(6) 2_645 no O16 O16 3.039(6) 2_755 no O16 O11 3.063(6) 2_745 no O9 H14 2.87(2) 3_675 no O9 H8 2.37(2) . no O10 H14 1.76(2) 3_675 no O10 H17 2.02(2) 1_465 no O10 H5 2.518(19) . no O11 H15 2.17(2) 2_655 no O11 H18 2.46(2) 2_755 no O13 H5 2.38(2) 1_645 no O13 H18 2.16(2) . no O16 H15 2.24(2) . no O16 H18 2.63(2) 2_755 no C1 O13 3.402(6) 1_565 no C2 O13 3.315(6) 1_465 no C4 O9 3.323(7) 3_665 no C4 C7 3.389(5) 1_565 no C4 O10 3.364(8) 3_675 no C6 O16 3.056(5) 2_755 no C6 O13 3.256(6) 1_455 no C7 C4 3.389(5) 1_545 no C12 O16 3.045(5) 2_755 no C2 H15 3.064(17) 2_655 no C4 H17 3.00(2) 1_465 no C4 H14 2.62(2) 3_675 no C6 H18 2.75(2) 2_755 no C6 H15 2.93(2) 2_655 no C12 H18 2.84(2) 2_755 no H5 O10 2.518(19) . no H5 O13 2.38(2) 1_465 no H5 H17 2.33(3) 1_465 no H8 O9 2.37(2) . no H8 H17 2.49(3) . no H14 O9 2.87(2) 3_675 no H14 O10 1.76(2) 3_675 no H14 C4 2.62(2) 3_675 no H14 H14 2.31(3) 3_675 no H15 O16 2.24(2) . no H15 O11 2.17(2) 2_645 no H15 C2 3.064(17) 2_645 no H15 C6 2.93(2) 2_645 no H15 H18 2.17(3) 2_755 no H17 O10 2.02(2) 1_645 no H17 C4 3.00(2) 1_645 no H17 H5 2.33(3) 1_645 no H17 H8 2.49(3) . no H18 O13 2.16(2) . no H18 O11 2.46(2) 2_745 no H18 O16 2.63(2) 2_745 no H18 C6 2.75(2) 2_745 no H18 C12 2.84(2) 2_745 no H18 H15 2.17(3) 2_745 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O9 H14 O10 0.916(19) 1.76(2) 2.624(9) 156.3(17) 3_675 yes O11 H15 O16 0.893(19) 2.24(2) 2.717(6) 113.3(14) . yes O11 H15 O11 0.893(19) 2.17(2) 2.868(5) 134.7(17) 2_645 yes O13 H17 O10 0.879(19) 2.02(2) 2.828(8) 153.3(19) 1_645 yes O16 H18 O13 0.88(2) 2.16(2) 2.635(6) 112.9(17) . yes O16 H18 O11 0.88(2) 2.46(2) 3.063(6) 126.1(18) 2_745 yes C2 H5 O10 0.94(2) 2.518(19) 2.842(8) 100.3(13) . yes C2 H5 O13 0.94(2) 2.38(2) 3.315(6) 169.7(17) 1_465 yes C3 H8 O9 0.923(17) 2.37(2) 2.742(7) 104.1(14) . 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 _geom_torsion_publ_flag C3 C1 C2 C6 0.3(5) no C4 C1 C2 C6 -179.6(3) no C2 C1 C3 C7 -0.2(5) no C4 C1 C3 C7 179.7(3) no C2 C1 C4 O9 171.9(4) no C2 C1 C4 O10 -2.6(7) no C3 C1 C4 O9 -8.0(6) no C3 C1 C4 O10 177.6(5) no C1 C2 C6 O11 179.7(4) no C1 C2 C6 C12 -0.2(5) no C1 C3 C7 O13 179.5(4) no C1 C3 C7 C12 0.0(5) no O11 C6 C12 O16 -0.3(5) no O11 C6 C12 C7 -179.9(3) no C2 C6 C12 O16 179.6(3) no C2 C6 C12 C7 0.1(5) no O13 C7 C12 O16 0.9(5) no O13 C7 C12 C6 -179.6(3) no C3 C7 C12 O16 -179.5(3) no C3 C7 C12 C6 0.0(5) no