#------------------------------------------------------------------------------ #$Date: 2016-03-24 01:30:03 +0200 (Thu, 24 Mar 2016) $ #$Revision: 179532 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/01/4500159.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_4500159 loop_ _publ_author_name 'Braun, Doris E.' 'Karamertzanis, Panagiotis G.' 'Arlin, Jean-Baptiste' 'Florence, Alastair J.' 'Kahlenberg, Volker' 'Tocher, Derek A.' 'Griesser, Ulrich J.' 'Price, Sarah L.' _publ_section_title ; Solid-State Forms of \b-Resorcylic Acid: How Exhaustive Should a Polymorph Screen Be? ; _journal_issue 1 _journal_name_full 'Crystal growth & design' _journal_page_first 210 _journal_page_last 220 _journal_paper_doi 10.1021/cg101162a _journal_volume 11 _journal_year 2011 _chemical_formula_moiety '2(C7 H6 O4), H2 O' _chemical_formula_sum 'C14 H14 O9' _chemical_formula_weight 326.25 _chemical_name_common 'beta resoryclic acid hemihydrate' _chemical_name_systematic '2,4-hidyroxybenzoic acid hemihydrate' _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_creation_date 2010-01-27T11:03:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 96.684(4) _cell_angle_beta 104.319(5) _cell_angle_gamma 98.903(4) _cell_formula_units_Z 2 _cell_length_a 7.0270(4) _cell_length_b 9.5449(4) _cell_length_c 11.1763(5) _cell_measurement_reflns_used 2711 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.3288 _cell_measurement_theta_min 3.0398 _cell_volume 708.15(6) _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR2002 (Burla et al., 2002)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 10.3822 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Oxford diffraction GEMINI R ULTRA' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0636111129 _diffrn_orient_matrix_UB_12 -0.026887591 _diffrn_orient_matrix_UB_13 0.0357525439 _diffrn_orient_matrix_UB_21 0.0814328179 _diffrn_orient_matrix_UB_22 -0.0220854644 _diffrn_orient_matrix_UB_23 0.0397651844 _diffrn_orient_matrix_UB_31 0.0240458356 _diffrn_orient_matrix_UB_32 0.0677567315 _diffrn_orient_matrix_UB_33 0.0392414093 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_unetI/netI 0.0286 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4832 _diffrn_reflns_theta_full 25.49 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_min 3.05 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_correction_T_min 0.9585 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.53 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'platy fragment' _exptl_crystal_F_000 340 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.401 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 239 _refine_ls_number_reflns 2604 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.966 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0382 _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^)+(0.0548P)^2^+0.1845P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0941 _refine_ls_wR_factor_ref 0.0996 _reflns_number_gt 2081 _reflns_number_total 2604 _reflns_threshold_expression >2sigma(I) _cod_data_source_file cg101162a_si_003.cif _cod_data_source_block bra_hh_1 _cod_database_code 4500159 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags O8 O 0.65869(17) 1.16682(12) 0.91065(12) 0.0255(3) Uani 1 1 d . H9 H 0.598(3) 1.204(2) 0.952(2) 0.044(7) Uiso 1 1 d . O7 O 0.03232(17) 0.84726(13) 0.77128(12) 0.0288(3) Uani 1 1 d . H8 H -0.023(3) 0.769(2) 0.716(2) 0.043 Uiso 1 1 d . O6 O -0.00613(17) 0.63595(12) 0.59730(10) 0.0247(3) Uani 1 1 d . C8 C 0.2971(2) 0.80440(16) 0.67731(15) 0.0199(4) Uani 1 1 d . C10 C 0.3405(2) 1.00638(17) 0.84099(15) 0.0200(4) Uani 1 1 d . H10 H 0.2882 1.0605 0.8978 0.024 Uiso 1 1 calc R O5 O 0.25346(19) 0.60562(13) 0.52180(12) 0.0286(3) Uani 1 1 d . H7 H 0.167(4) 0.528(3) 0.484(2) 0.055(7) Uiso 1 1 d . C13 C 0.4960(2) 0.84998(17) 0.67571(16) 0.0233(4) Uani 1 1 d . H12 H 0.5497 0.7964 0.6194 0.028 Uiso 1 1 calc R C9 C 0.2224(2) 0.88530(16) 0.76259(15) 0.0192(4) Uani 1 1 d . C11 C 0.5360(2) 1.04871(16) 0.83650(15) 0.0199(4) Uani 1 1 d . C14 C 0.1705(2) 0.67640(16) 0.59666(15) 0.0202(4) Uani 1 1 d . C12 C 0.6143(2) 0.96972(17) 0.75335(16) 0.0241(4) Uani 1 1 d . H11 H 0.7485 0.999 0.7508 0.029 Uiso 1 1 calc R C1 C 0.2456(2) 0.31066(16) 0.69755(15) 0.0197(4) Uani 1 1 d . O4 O 0.52829(19) 0.68570(12) 0.94421(11) 0.0240(3) Uani 1 1 d . H3 H 0.648(4) 0.705(2) 0.948(2) 0.044(6) Uiso 1 1 d . O3 O -0.04790(18) 0.33482(13) 0.76896(12) 0.0317(3) Uani 1 1 d . H2 H -0.093(4) 0.247(3) 0.706(2) 0.068(7) Uiso 1 1 d . O2 O -0.03524(17) 0.12486(11) 0.60120(10) 0.0248(3) Uani 1 1 d . C3 C 0.2416(2) 0.50879(16) 0.85290(15) 0.0217(4) Uani 1 1 d . H4 H 0.1718 0.5581 0.9016 0.026 Uiso 1 1 calc R O1 O 0.24681(18) 0.12015(13) 0.54440(11) 0.0266(3) Uani 1 1 d . H1 H 0.173(3) 0.040(2) 0.497(2) 0.045(6) Uiso 1 1 d . C4 C 0.4406(2) 0.56254(16) 0.86314(14) 0.0190(4) Uani 1 1 d . C6 C 0.4472(2) 0.36771(17) 0.71006(15) 0.0222(4) Uani 1 1 d . H6 H 0.5177 0.3196 0.661 0.027 Uiso 1 1 calc R C2 C 0.1448(2) 0.38346(17) 0.77175(15) 0.0200(4) Uani 1 1 d . C7 C 0.1423(2) 0.17901(16) 0.61169(14) 0.0200(4) Uani 1 1 d . C5 C 0.5451(2) 0.49169(17) 0.79165(16) 0.0234(4) Uani 1 1 d . H5 H 0.6819 0.5286 0.7993 0.028 Uiso 1 1 calc R O9 O 0.9107(2) 0.7777(2) 0.98332(16) 0.0480(4) Uani 1 1 d . H13 H 0.960(4) 0.809(3) 0.933(3) 0.068(9) Uiso 1 1 d . H14 H 1.000(5) 0.765(3) 1.041(3) 0.083(10) Uiso 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O8 0.0186(6) 0.0230(6) 0.0295(7) -0.0051(5) 0.0051(5) -0.0027(5) O7 0.0190(6) 0.0285(7) 0.0347(7) -0.0066(5) 0.0096(5) -0.0026(5) O6 0.0219(6) 0.0221(6) 0.0254(7) -0.0019(5) 0.0030(5) 0.0001(5) C8 0.0207(8) 0.0193(8) 0.0189(8) 0.0047(7) 0.0030(7) 0.0042(7) C10 0.0199(8) 0.0200(8) 0.0203(8) 0.0020(6) 0.0060(7) 0.0043(6) O5 0.0285(7) 0.0227(6) 0.0298(7) -0.0086(5) 0.0080(6) -0.0005(5) C13 0.0235(9) 0.0220(8) 0.0255(9) 0.0009(7) 0.0094(7) 0.0051(7) C9 0.0173(8) 0.0199(8) 0.0206(9) 0.0059(6) 0.0045(7) 0.0031(6) C11 0.0186(8) 0.0181(8) 0.0203(9) 0.0032(6) 0.0013(7) 0.0017(6) C14 0.0212(9) 0.0199(8) 0.0187(9) 0.0047(6) 0.0026(7) 0.0054(7) C12 0.0170(8) 0.0237(8) 0.0317(10) 0.0037(7) 0.0091(7) 0.0008(7) C1 0.0200(9) 0.0187(8) 0.0187(8) 0.0042(6) 0.0020(7) 0.0031(7) O4 0.0189(6) 0.0215(6) 0.0260(7) -0.0052(5) 0.0033(5) -0.0016(5) O3 0.0212(7) 0.0333(7) 0.0355(8) -0.0054(6) 0.0081(6) -0.0025(5) O2 0.0223(6) 0.0220(6) 0.0255(7) -0.0022(5) 0.0041(5) -0.0016(5) C3 0.0222(9) 0.0213(8) 0.0213(9) 0.0009(7) 0.0059(7) 0.0053(7) O1 0.0270(7) 0.0222(6) 0.0267(7) -0.0057(5) 0.0072(5) 0.0004(5) C4 0.0209(8) 0.0156(8) 0.0178(8) 0.0021(6) 0.0011(7) 0.0022(7) C6 0.0211(9) 0.0216(8) 0.0235(9) 0.0006(7) 0.0067(7) 0.0045(7) C2 0.0159(8) 0.0224(8) 0.0205(9) 0.0052(7) 0.0028(7) 0.0024(7) C7 0.0230(9) 0.0193(8) 0.0175(9) 0.0052(7) 0.0040(7) 0.0041(7) C5 0.0165(8) 0.0246(8) 0.0269(9) 0.0021(7) 0.0050(7) 0.0003(7) O9 0.0207(7) 0.0845(12) 0.0322(9) 0.0104(8) 0.0038(7) -0.0051(7) 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 C11 O8 H9 108.5(17) C9 O7 H8 106.6(14) C13 C8 C9 117.92(15) C13 C8 C14 122.16(14) C9 C8 C14 119.91(14) C9 C10 C11 119.61(14) C9 C10 H10 120.2 C11 C10 H10 120.2 C14 O5 H7 107.2(15) C12 C13 C8 121.50(15) C12 C13 H12 119.2 C8 C13 H12 119.2 O7 C9 C10 117.46(13) O7 C9 C8 121.60(14) C10 C9 C8 120.95(14) O8 C11 C10 122.31(14) O8 C11 C12 117.09(14) C10 C11 C12 120.60(15) O6 C14 O5 121.69(14) O6 C14 C8 122.40(14) O5 C14 C8 115.91(14) C13 C12 C11 119.42(15) C13 C12 H11 120.3 C11 C12 H11 120.3 C6 C1 C2 118.16(14) C6 C1 C7 121.50(14) C2 C1 C7 120.34(14) C4 O4 H3 110.2(15) C2 O3 H2 105.6(15) C2 C3 C4 119.90(15) C2 C3 H4 120 C4 C3 H4 120 C7 O1 H1 109.6(14) O4 C4 C3 117.44(14) O4 C4 C5 121.83(14) C3 C4 C5 120.73(14) C5 C6 C1 121.53(15) C5 C6 H6 119.2 C1 C6 H6 119.2 O3 C2 C3 116.83(14) O3 C2 C1 122.56(14) C3 C2 C1 120.60(15) O2 C7 O1 121.36(14) O2 C7 C1 122.51(14) O1 C7 C1 116.12(14) C6 C5 C4 119.06(15) C6 C5 H5 120.5 C4 C5 H5 120.5 H13 O9 H14 108(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O8 C11 1.3526(19) O8 H9 0.79(2) O7 C9 1.3594(19) O7 H8 0.88(2) O6 C14 1.2434(19) C8 C13 1.403(2) C8 C9 1.408(2) C8 C14 1.452(2) C10 C9 1.378(2) C10 C11 1.385(2) C10 H10 0.95 O5 C14 1.3146(19) O5 H7 0.87(3) C13 C12 1.367(2) C13 H12 0.95 C11 C12 1.398(2) C12 H11 0.95 C1 C6 1.403(2) C1 C2 1.408(2) C1 C7 1.456(2) O4 C4 1.3543(19) O4 H3 0.82(2) O3 C2 1.3529(19) O3 H2 0.98(3) O2 C7 1.2458(19) C3 C2 1.381(2) C3 C4 1.385(2) C3 H4 0.95 O1 C7 1.3124(19) O1 H1 0.88(2) C4 C5 1.397(2) C6 C5 1.375(2) C6 H6 0.95 C5 H5 0.95 O9 H13 0.79(3) O9 H14 0.81(3) 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 C9 C8 C13 C12 -0.6(2) C14 C8 C13 C12 -179.14(15) C11 C10 C9 O7 179.37(14) C11 C10 C9 C8 -0.4(2) C13 C8 C9 O7 -179.06(14) C14 C8 C9 O7 -0.4(2) C13 C8 C9 C10 0.7(2) C14 C8 C9 C10 179.33(14) C9 C10 C11 O8 179.69(15) C9 C10 C11 C12 -0.1(2) C13 C8 C14 O6 -179.65(15) C9 C8 C14 O6 1.8(2) C13 C8 C14 O5 0.0(2) C9 C8 C14 O5 -178.60(13) C8 C13 C12 C11 0.1(3) O8 C11 C12 C13 -179.55(15) C10 C11 C12 C13 0.2(2) C2 C3 C4 O4 -179.94(14) C2 C3 C4 C5 0.3(2) C2 C1 C6 C5 -0.4(2) C7 C1 C6 C5 -179.65(15) C4 C3 C2 O3 178.19(14) C4 C3 C2 C1 -1.0(2) C6 C1 C2 O3 -178.12(14) C7 C1 C2 O3 1.2(2) C6 C1 C2 C3 1.0(2) C7 C1 C2 C3 -179.67(15) C6 C1 C7 O2 178.37(14) C2 C1 C7 O2 -0.9(2) C6 C1 C7 O1 -2.1(2) C2 C1 C7 O1 178.61(13) C1 C6 C5 C4 -0.3(2) O4 C4 C5 C6 -179.38(15) C3 C4 C5 C6 0.3(2)