# CIF-file generated for #============================================================================== data_Pyrogallol_tetarto_hydrate_powder_structure #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Doris E. Braun' _publ_contact_author_address ; Institute of Pharmacy University of Innsbruck Innrain 52c 6020 Innsbruck Austria ; _publ_contact_author_phone '43 (0)512 507 5306' _publ_contact_author_fax '43 (0)512 507 58499' _publ_contact_author_email 'doris.braun@uibk.ac.at' _publ_requested_journal 'Crystal Growth and Design' # TITLE AND AUTHOR LIST _publ_section_title ; Absorbing a little water: the structural, thermodynamic and kinetic relationship between pyrogallol and its tetarto-hydrate ; loop_ _publ_author_name _publ_author_address 'Doris E. Braun' ; Institute of Pharmacy University of Innsbruck Innrain 52 6020 Innsbruck Austria ; 'Rajni Miglani' ; University of Strathclyde Strathclyde Institute of Pharmacy and Biomedical Sciences 161 Cathedral Street Glasgow G4 0RE United Kingdom ; 'Jean-Baptiste Arlin' ; Institut Charles Sadron (UPR22-CNRS) 23 rue du Loess BP 84047 67034 STRASBOURG Cedex France ; 'Alastair J. Florence' ; University of Strathclyde Strathclyde Institute of Pharmacy and Biomedical Sciences 27 Taylor Street Glasgow G4 0NR United Kingdom ; 'Volker Kahlenberg' ; Institute of Mineralogy and Petrography University of Innsbruck Innrain 52 6020 Innsbruck Austria ; 'Ulrich J. Griesser' ; Institute of Pharmacy University of Innsbruck Innrain 52 6020 Innsbruck Austria ; 'Derek A. Tocher' ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; 'Sarah L. Price' ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; _chemical_name_systematic ; 1,2,3-trihydroxybenzene ; _chemical_name_common 'pyrogallol_tetartohydrate' _chemical_formula_sum 'C24 H26 O13' _chemical_formula_moiety '4(C6 H6 O3), H2 O' _chemical_formula_weight 522.45 _exptl_crystal_colour colourless _exptl_crystal_preparation ; to be added Pyragallol tetrato hydrate crystals were obtained by cooling crystallisation from ethanol the powder produced was loaded in a 1.0 mm borosilicate glass capillary, mounted on Bruker AXS D8 X-ray powder diffractometer equipped with primary monochromator (CuKa1, l = 1.54056A) and a Lynxeye position sensitive detector. Collection was made at room temperature. ; #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Tetragonal _symmetry_space_group_name_Hall '-P 4bc' _symmetry_space_group_name_H-M 'P 42/n' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -y,1/2+x,1/2+z 3 1/2-x,1/2-y,z 4 1/2+y,-x,1/2+z 5 -x,-y,-z 6 y,1/2-x,1/2-z 7 1/2+x,1/2+y,-z 8 1/2-y,x,1/2-z _cell_length_a 24.6058(6) _cell_length_b 24.6058(6) _cell_length_c 3.8524(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2332.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_wavelength 1.54056 _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54056 _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'Not Measured' _pd_proc_ls_prof_R_factor 0.050 _pd_proc_ls_prof_wR_factor 0.055 _pd_proc_ls_prof_wR_expected 0.018 _refine_ls_goodness_of_fit_all 3.05 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 _atom_site_calc_flag _atom_site_refinement_flags O1Z O Uiso 0.54649(8) 0.89245(11) 0.2692(7) 1.000 0.0380 . . O2Z O Uiso 0.59575(8) 0.98335(7) 0.5055(7) 1.000 0.0380 . . O3Z O Uiso 0.69999(9) 0.98169(10) 0.7375(6) 1.000 0.0380 . . C1Z C Uiso 0.59960(8) 0.88669(7) 0.3806(5) 1.000 0.0380 . . C2Z C Uiso 0.62324(7) 0.93467(7) 0.5008(4) 1.000 0.0380 . . C3Z C Uiso 0.67681(7) 0.93459(8) 0.6206(4) 1.000 0.0380 . . C4Z C Uiso 0.70655(8) 0.88633(10) 0.6220(7) 1.000 0.0380 . . C5Z C Uiso 0.68253(11) 0.83858(8) 0.5014(9) 1.000 0.0380 . . C6Z C Uiso 0.62894(11) 0.83827(7) 0.3809(7) 1.000 0.0380 . . O4Z O Uiso 0.35513(8) 0.93835(10) 0.8957(8) 1.000 0.0380 . . O5Z O Uiso 0.45733(8) 0.90946(8) 0.7175(6) 1.000 0.0380 . . O6Z O Uiso 0.49684(9) 0.80878(9) 0.8591(6) 1.000 0.0380 . . C7Z C Uiso 0.37079(6) 0.88605(9) 0.9810(5) 1.000 0.0380 . . C8Z C Uiso 0.42387(6) 0.87308(7) 0.8844(4) 1.000 0.0380 . . C9Z C Uiso 0.44484(8) 0.82150(7) 0.9547(4) 1.000 0.0380 . . C10Z C Uiso 0.41268(11) 0.78303(8) 1.1238(5) 1.000 0.0380 . . C11Z C Uiso 0.35968(11) 0.79641(11) 1.2195(6) 1.000 0.0380 . . C12Z C Uiso 0.33833(8) 0.84793(11) 1.1501(6) 1.000 0.0380 . . O7Z O Uiso 0.5068(3) 0.0042(3) 0.8511(15) 0.500 0.0380 . . H1Z H Uiso 0.53425(10) 0.86002(12) 0.1947(8) 1.000 0.0456 . . H2Z H Uiso 0.56225(8) 0.97700(9) 0.4210(8) 1.000 0.0456 . . H3Z H Uiso 0.67468(11) 1.00790(8) 0.7171(7) 1.000 0.0456 . . H4Z H Uiso 0.74293(9) 0.88701(12) 0.7045(9) 1.000 0.0456 . . H5Z H Uiso 0.70277(14) 0.80570(9) 0.5023(12) 1.000 0.0456 . . H6Z H Uiso 0.61263(14) 0.80571(7) 0.2989(9) 1.000 0.0456 . . H7Z H Uiso 0.50760(11) 0.77498(10) 0.9159(8) 1.000 0.0456 . . H8Z H Uiso 0.48997(8) 0.89444(10) 0.6740(6) 1.000 0.0456 . . H9Z H Uiso 0.38221(10) 0.95622(8) 0.7879(8) 1.000 0.0456 . . H10Z H Uiso 0.42761(14) 0.74815(8) 1.1696(7) 1.000 0.0456 . . H11Z H Uiso 0.33776(13) 0.77022(13) 1.3346(8) 1.000 0.0456 . . H12Z H Uiso 0.30222(8) 0.85700(14) 1.2154(8) 1.000 0.0456 . . #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1Z C1Z 1.383(3) . . yes O2Z C2Z 1.376(2) . . yes O3Z C3Z 1.368(3) . . yes O1Z H1Z 0.900(4) . . no O2Z H2Z 0.900(3) . . no O3Z H3Z 0.900(3) . . no O4Z C7Z 1.383(3) . . yes O5Z C8Z 1.376(3) . . yes O6Z C9Z 1.368(3) . . yes O4Z H9Z 0.900(3) . . no O5Z H8Z 0.900(3) . . no O6Z H7Z 0.900(3) . . no C1Z C6Z 1.393(3) . . no C1Z C2Z 1.395(2) . . no C2Z C3Z 1.397(2) . . no C3Z C4Z 1.395(3) . . no C4Z C5Z 1.395(3) . . no C5Z C6Z 1.398(4) . . no C4Z H4Z 0.950(3) . . no C5Z H5Z 0.950(3) . . no C6Z H6Z 0.950(3) . . no C7Z C12Z 1.394(3) . . no C7Z C8Z 1.395(2) . . no C8Z C9Z 1.397(2) . . no C9Z C10Z 1.395(3) . . no C10Z C11Z 1.395(4) . . no C11Z C12Z 1.398(4) . . no C10Z H10Z 0.950(3) . . no C11Z H11Z 0.950(4) . . no C12Z H12Z 0.950(3) . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1Z O1Z H1Z 108.9(3) . . . no C2Z O2Z H2Z 107.1(2) . . . no C3Z O3Z H3Z 106.9(3) . . . no C7Z O4Z H9Z 111.0(2) . . . no C8Z O5Z H8Z 110.7(2) . . . no C9Z O6Z H7Z 114.9(3) . . . no O1Z C1Z C6Z 125.3(2) . . . yes O1Z C1Z C2Z 114.22(18) . . . yes C2Z C1Z C6Z 120.49(19) . . . no C1Z C2Z C3Z 120.13(17) . . . no O2Z C2Z C3Z 117.45(17) . . . yes O2Z C2Z C1Z 122.42(17) . . . yes C2Z C3Z C4Z 119.84(18) . . . no O3Z C3Z C4Z 120.08(18) . . . yes O3Z C3Z C2Z 120.07(18) . . . yes C3Z C4Z C5Z 119.57(19) . . . no C4Z C5Z C6Z 120.99(19) . . . no C1Z C6Z C5Z 118.98(18) . . . no C3Z C4Z H4Z 118.7(3) . . . no C5Z C4Z H4Z 121.7(3) . . . no C4Z C5Z H5Z 119.6(3) . . . no C6Z C5Z H5Z 119.4(3) . . . no C5Z C6Z H6Z 120.9(3) . . . no C1Z C6Z H6Z 120.1(3) . . . no O4Z C7Z C12Z 125.29(18) . . . yes O4Z C7Z C8Z 114.23(17) . . . yes C8Z C7Z C12Z 120.48(19) . . . no O5Z C8Z C7Z 122.42(17) . . . yes O5Z C8Z C9Z 117.44(15) . . . yes C7Z C8Z C9Z 120.14(16) . . . no C8Z C9Z C10Z 119.84(18) . . . no O6Z C9Z C8Z 120.09(17) . . . yes O6Z C9Z C10Z 120.07(19) . . . yes C9Z C10Z C11Z 119.6(2) . . . no C10Z C11Z C12Z 121.0(2) . . . no C7Z C12Z C11Z 119.0(2) . . . no C9Z C10Z H10Z 118.7(3) . . . no C11Z C10Z H10Z 121.7(3) . . . no C10Z C11Z H11Z 119.6(3) . . . no C12Z C11Z H11Z 119.4(3) . . . no C7Z C12Z H12Z 120.1(3) . . . no C11Z C12Z H12Z 120.9(3) . . . no 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1Z C1Z C2Z O2Z -0.3(3) . . . . no O1Z C1Z C2Z C3Z -179.90(18) . . . . no C6Z C1Z C2Z O2Z -179.9(2) . . . . no C6Z C1Z C2Z C3Z 0.4(3) . . . . no O1Z C1Z C6Z C5Z 180.0(3) . . . . no C2Z C1Z C6Z C5Z -0.4(4) . . . . no O2Z C2Z C3Z O3Z 0.2(3) . . . . no O2Z C2Z C3Z C4Z 179.9(2) . . . . no C1Z C2Z C3Z O3Z 179.82(18) . . . . no C1Z C2Z C3Z C4Z -0.4(3) . . . . no O3Z C3Z C4Z C5Z -179.9(2) . . . . no C2Z C3Z C4Z C5Z 0.4(3) . . . . no C3Z C4Z C5Z C6Z -0.4(4) . . . . no C4Z C5Z C6Z C1Z 0.4(4) . . . . no O4Z C7Z C8Z O5Z -0.2(3) . . . . no O4Z C7Z C8Z C9Z -179.91(18) . . . . no C12Z C7Z C8Z O5Z -179.9(2) . . . . no C12Z C7Z C8Z C9Z 0.4(3) . . . . no O4Z C7Z C12Z C11Z 180.0(2) . . . . no C8Z C7Z C12Z C11Z -0.4(3) . . . . no O5Z C8Z C9Z O6Z 0.2(3) . . . . no O5Z C8Z C9Z C10Z 179.93(18) . . . . no C7Z C8Z C9Z O6Z 179.84(18) . . . . no C7Z C8Z C9Z C10Z -0.4(2) . . . . no O6Z C9Z C10Z C11Z -179.9(2) . . . . no C8Z C9Z C10Z C11Z 0.4(3) . . . . no C9Z C10Z C11Z C12Z -0.3(3) . . . . no C10Z C11Z C12Z C7Z 0.3(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1Z O2Z 2.702(3) . . no O1Z O5Z 3.083(3) . 1_554 no O1Z O5Z 2.823(3) . . no O1Z O6Z 2.868(3) . 1_554 no O1Z C8Z 3.395(3) . 1_554 no O1Z C9Z 3.282(3) . 1_554 no O1Z O7Z 2.899(8) . 5_666 no O2Z O4Z 2.750(3) . 5_676 no O2Z O4Z 3.240(4) . 5_677 no O2Z O7Z 2.613(7) . 1_565 no O2Z O1Z 2.702(3) . . no O2Z O3Z 2.717(3) . . no O2Z O5Z 3.066(3) . 5_676 no O2Z O7Z 2.889(7) . 5_666 no O3Z O6Z 2.754(3) . 6_566 no O3Z O4Z 2.776(3) . 5_677 no O3Z O2Z 2.717(3) . . no O4Z O3Z 2.776(3) . 5_677 no O4Z O2Z 3.240(4) . 5_677 no O4Z O5Z 2.702(3) . . no O4Z O2Z 2.750(3) . 5_676 no O5Z O2Z 3.066(3) . 5_676 no O5Z O7Z 3.177(7) . 5_666 no O5Z O7Z 2.838(7) . 5_667 no O5Z O7Z 2.680(8) . 1_565 no O5Z O1Z 3.083(3) . 1_556 no O5Z O1Z 2.823(3) . . no O5Z O6Z 2.717(3) . . no O5Z O4Z 2.702(3) . . no O6Z O3Z 2.754(3) . 8_656 no O6Z O1Z 2.868(3) . 1_556 no O6Z O5Z 2.717(3) . . no O7Z O2Z 2.613(7) . 1_545 no O7Z O2Z 2.889(7) . 5_666 no O7Z O5Z 2.838(7) . 5_667 no O7Z O5Z 2.680(8) . 1_545 no O7Z O5Z 3.177(7) . 5_666 no O7Z O1Z 2.899(8) . 5_666 no O1Z H8Z 2.682(3) . 1_554 no O1Z H2Z 2.196(4) . . no O1Z H8Z 2.090(3) . . no O2Z H3Z 2.191(3) . . no O2Z H9Z 1.945(3) . 5_676 no O3Z H7Z 1.955(3) . 6_566 no O4Z H3Z 2.804(4) . 5_676 no O4Z H3Z 2.124(4) . 5_677 no O4Z H10Z 2.699(3) . 2_654 no O5Z H2Z 2.885(3) . 5_676 no O5Z H1Z 2.906(4) . 1_556 no O5Z H9Z 2.194(3) . . no O6Z H1Z 2.027(4) . 1_556 no O6Z H8Z 2.232(3) . . no O7Z H8Z 2.816(8) . 1_545 no O7Z H2Z 2.049(7) . 5_666 no O7Z H2Z 2.670(7) . 1_546 no O7Z H2Z 2.248(7) . 1_545 no C7Z C12Z 3.430(3) . 1_554 no C8Z C12Z 3.580(3) . 1_554 no C8Z O1Z 3.395(3) . 1_556 no C8Z C11Z 3.552(3) . 1_554 no C9Z C11Z 3.577(3) . 1_554 no C9Z O1Z 3.282(3) . 1_556 no C9Z C10Z 3.431(3) . 1_554 no C10Z C9Z 3.431(3) . 1_556 no C11Z C8Z 3.552(3) . 1_556 no C11Z C9Z 3.577(3) . 1_556 no C12Z C7Z 3.430(3) . 1_556 no C12Z C8Z 3.580(3) . 1_556 no C1Z H8Z 2.931(3) . . no C2Z H9Z 2.909(3) . 5_676 no C3Z H7Z 2.807(3) . 6_566 no C4Z H6Z 2.930(3) . 6_565 no C6Z H4Z 2.865(3) . 8_656 no C7Z H3Z 3.068(3) . 5_677 no C8Z H1Z 2.985(3) . 1_556 no C9Z H1Z 2.568(3) . 1_556 no C10Z H12Z 2.959(3) . 4_464 no C11Z H12Z 3.089(4) . 4_465 no C12Z H11Z 2.945(4) . 2_654 no H1Z O5Z 2.906(4) . 1_554 no H1Z H7Z 2.442(4) . 1_554 no H1Z H8Z 2.435(4) . 1_554 no H1Z H8Z 2.305(4) . . no H1Z O6Z 2.027(4) . 1_554 no H1Z C8Z 2.985(3) . 1_554 no H1Z C9Z 2.568(3) . 1_554 no H1Z H6Z 2.380(4) . . no H2Z O7Z 2.670(7) . 1_564 no H2Z O7Z 2.049(7) . 5_666 no H2Z O5Z 2.885(3) . 5_676 no H2Z O1Z 2.196(4) . . no H2Z H9Z 2.284(3) . 5_676 no H2Z O7Z 2.248(7) . 1_565 no H3Z H9Z 2.554(4) . 5_676 no H3Z C7Z 3.068(3) . 5_677 no H3Z O2Z 2.191(3) . . no H3Z O4Z 2.804(4) . 5_676 no H3Z O4Z 2.124(4) . 5_677 no H3Z H9Z 2.525(4) . 5_677 no H3Z H7Z 2.549(4) . 6_566 no H4Z C6Z 2.865(3) . 6_566 no H4Z H6Z 2.459(4) . 6_566 no H4Z H6Z 2.479(4) . 6_565 no H6Z C4Z 2.930(3) . 8_655 no H6Z H4Z 2.459(4) . 8_656 no H6Z H1Z 2.380(4) . . no H6Z H4Z 2.479(4) . 8_655 no H7Z H1Z 2.442(4) . 1_556 no H7Z H3Z 2.549(4) . 8_656 no H7Z C3Z 2.807(3) . 8_656 no H7Z H10Z 2.295(4) . . no H7Z O3Z 1.955(3) . 8_656 no H8Z O1Z 2.682(3) . 1_556 no H8Z C1Z 2.931(3) . . no H8Z O6Z 2.232(3) . . no H8Z O7Z 2.816(8) . 1_565 no H8Z O1Z 2.090(3) . . no H8Z H1Z 2.435(4) . 1_556 no H8Z H1Z 2.305(4) . . no H9Z O2Z 1.945(3) . 5_676 no H9Z O5Z 2.194(3) . . no H9Z H3Z 2.554(4) . 5_676 no H9Z C2Z 2.909(3) . 5_676 no H9Z H2Z 2.284(3) . 5_676 no H9Z H3Z 2.525(4) . 5_677 no H10Z O4Z 2.699(3) . 4_465 no H10Z H7Z 2.295(4) . . no H11Z H12Z 2.357(4) . 4_465 no H11Z C12Z 2.945(4) . 4_465 no H12Z C10Z 2.959(3) . 2_655 no H12Z C11Z 3.089(4) . 2_654 no H12Z H11Z 2.357(4) . 2_654 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 # #D H A D - H H...A D...A D - H...A symm(A) # O1Z H1Z O6Z 0.900(4) 2.027(4) 2.868(3) 155.1(3) 1_554 yes O2Z H2Z O1Z 0.900(3) 2.196(4) 2.702(3) 115.0(2) . yes O2Z H2Z O7Z 0.900(3) 2.248(7) 2.613(7) 103.7(3) 1_565 yes O2Z H2Z O7Z 0.900(3) 2.049(7) 2.889(7) 154.9(3) 5_666 yes O3Z H3Z O2Z 0.900(3) 2.191(3) 2.717(3) 116.6(2) . yes O3Z H3Z O4Z 0.900(3) 2.124(4) 2.776(3) 128.6(3) 5_677 yes O6Z H7Z O3Z 0.900(3) 1.955(3) 2.754(3) 147.0(3) 8_656 yes O5Z H8Z O1Z 0.900(3) 2.090(3) 2.823(3) 137.9(3) . yes O5Z H8Z O6Z 0.900(3) 2.232(3) 2.717(3) 113.3(2) . yes O4Z H9Z O5Z 0.900(3) 2.194(3) 2.702(3) 115.1(2) . yes O4Z H9Z O2Z 0.900(3) 1.945(3) 2.750(3) 148.0(3) 5_676 yes _refine_special_details ; A rigid body refinement was carried out using the best solution returned from the simulated annealing in TOPAS V4.1.The final refinement included a total of 44 parameters (26 profile, 2 cell, 1 scale, 9 position, 6 rotation), yielding a final Rwp= 5.573. The resulting structure was further scrutinised by allowing all fractional coordinates to refine freely (118 parameters, Rwp = 5.117). As expected, the improve Rwp came at the expense of some chemical sense (e.g. H atoms moving to nonsensical positions ), but otherwise, the geometry of the independent molecules was well preserved, confirming the correctness of the rigid-body refined crystal s structure. ; #===END