#------------------------------------------------------------------------------ #$Date: 2012-02-25 19:46:49 +0200 (Sat, 25 Feb 2012) $ #$Revision: 34378 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/01/4500160.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_4500160 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_volume 11 _journal_year 2011 _chemical_formula_moiety 'C7 H5 O4, C5 H6 N' _chemical_formula_sum 'C12 H11 N O4' _chemical_formula_weight 233.22 _chemical_name_common 'beta resoryclate pyridinium salt' _chemical_name_systematic '2,4-dihydroxybenzoate pyridinium salt' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 2010-01-19T20:03:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 115.973(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.7363(4) _cell_length_b 8.5691(2) _cell_length_c 11.8310(4) _cell_measurement_reflns_used 4246 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.3387 _cell_measurement_theta_min 3.0458 _cell_volume 1069.67(7) _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 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Oxford diffraction GEMINI R ULTRA' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0634787587 _diffrn_orient_matrix_UB_12 -0.0165472877 _diffrn_orient_matrix_UB_13 -0.0430612589 _diffrn_orient_matrix_UB_21 -0.0154035614 _diffrn_orient_matrix_UB_22 0.0802336803 _diffrn_orient_matrix_UB_23 -0.0014779077 _diffrn_orient_matrix_UB_31 0.0156762969 _diffrn_orient_matrix_UB_32 0.0117082657 _diffrn_orient_matrix_UB_33 -0.0508393888 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_unetI/netI 0.0206 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 7775 _diffrn_reflns_theta_full 25.34 _diffrn_reflns_theta_max 25.34 _diffrn_reflns_theta_min 3.05 _exptl_absorpt_coefficient_mu 0.11 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_correction_T_min 0.9145 _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 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_description fragment _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.189 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 1953 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0337 _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^)+(0.0487P)^2^+0.1579P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0839 _refine_ls_wR_factor_ref 0.0874 _reflns_number_gt 1639 _reflns_number_total 1953 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file cg101162a_si_004.cif _[local]_cod_data_source_block bra_pyr_1 _cod_original_cell_volume 1069.66(6) _cod_database_code 4500160 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 O1 O 0.44989(8) -0.10055(11) 0.14133(8) 0.0265(2) Uani 1 1 d . O4 O -0.00512(8) 0.32151(11) 0.12221(10) 0.0304(3) Uani 1 1 d . H2 H 0.0215(16) 0.344(2) 0.2084(17) 0.051(5) Uiso 1 1 d . O2 O 0.32489(9) -0.09715(11) -0.06319(9) 0.0323(3) Uani 1 1 d . O3 O 0.11586(9) 0.04733(12) -0.15182(8) 0.0332(3) Uani 1 1 d . H1 H 0.1894(18) -0.015(2) -0.1417(16) 0.061(5) Uiso 1 1 d . N1 N 0.41796(10) 0.27864(12) -0.05885(10) 0.0235(3) Uani 1 1 d . H6 H 0.4687(16) 0.2101(19) -0.0812(16) 0.047(5) Uiso 1 1 d . C2 C 0.14354(12) 0.09064(14) -0.03243(11) 0.0225(3) Uani 1 1 d . C6 C 0.28093(11) 0.09615(14) 0.18902(12) 0.0214(3) Uani 1 1 d . H5 H 0.3576 0.0666 0.2586 0.026 Uiso 1 1 calc R C1 C 0.25731(11) 0.04347(14) 0.06895(12) 0.0200(3) Uani 1 1 d . C4 C 0.08278(11) 0.23178(14) 0.10750(12) 0.0223(3) Uani 1 1 d . C12 C 0.45260(12) 0.33169(15) 0.05798(12) 0.0254(3) Uani 1 1 d . H11 H 0.5301 0.2977 0.1243 0.03 Uiso 1 1 calc R C5 C 0.19628(12) 0.18971(14) 0.20934(12) 0.0228(3) Uani 1 1 d . H4 H 0.2149 0.2252 0.2917 0.027 Uiso 1 1 calc R C9 C 0.23076(12) 0.42615(16) -0.13555(13) 0.0291(3) Uani 1 1 d . H8 H 0.1539 0.4584 -0.2037 0.035 Uiso 1 1 calc R C3 C 0.05701(12) 0.18317(15) -0.01271(12) 0.0255(3) Uani 1 1 d . H3 H -0.0199 0.2131 -0.0818 0.031 Uiso 1 1 calc R C7 C 0.34882(12) -0.05704(14) 0.04757(12) 0.0220(3) Uani 1 1 d . C11 C 0.37696(12) 0.43480(15) 0.08260(13) 0.0272(3) Uani 1 1 d . H10 H 0.4012 0.4728 0.1654 0.033 Uiso 1 1 calc R C8 C 0.30983(12) 0.32309(15) -0.15463(12) 0.0259(3) Uani 1 1 d . H7 H 0.2876 0.283 -0.2365 0.031 Uiso 1 1 calc R C10 C 0.26433(13) 0.48249(16) -0.01586(13) 0.0290(3) Uani 1 1 d . H9 H 0.2104 0.5538 -0.001 0.035 Uiso 1 1 calc R 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 O1 0.0216(5) 0.0340(5) 0.0260(5) 0.0010(4) 0.0125(4) 0.0049(4) O4 0.0241(5) 0.0367(6) 0.0307(6) -0.0009(4) 0.0122(4) 0.0091(4) O2 0.0341(5) 0.0397(6) 0.0251(5) -0.0055(4) 0.0149(4) 0.0055(4) O3 0.0338(6) 0.0424(6) 0.0184(5) -0.0045(4) 0.0068(4) 0.0062(5) N1 0.0230(6) 0.0236(6) 0.0284(6) 0.0032(5) 0.0154(5) 0.0018(5) C2 0.0246(7) 0.0230(7) 0.0195(7) -0.0009(5) 0.0094(6) -0.0038(6) C6 0.0190(6) 0.0243(7) 0.0199(7) 0.0011(5) 0.0077(5) 0.0001(5) C1 0.0194(6) 0.0198(6) 0.0224(7) 0.0004(5) 0.0106(6) -0.0029(5) C4 0.0204(6) 0.0215(6) 0.0281(7) 0.0018(5) 0.0135(6) 0.0007(5) C12 0.0200(6) 0.0293(7) 0.0243(7) 0.0054(6) 0.0073(6) 0.0008(6) C5 0.0256(7) 0.0251(7) 0.0192(7) 0.0007(5) 0.0113(6) 0.0007(6) C9 0.0228(7) 0.0321(8) 0.0266(8) 0.0039(6) 0.0055(6) 0.0038(6) C3 0.0202(6) 0.0284(7) 0.0232(7) 0.0023(6) 0.0053(6) 0.0019(6) C7 0.0225(7) 0.0223(7) 0.0243(7) 0.0005(5) 0.0131(6) -0.0030(5) C11 0.0275(7) 0.0307(7) 0.0230(7) -0.0018(6) 0.0105(6) 0.0004(6) C8 0.0291(7) 0.0279(7) 0.0211(7) 0.0029(6) 0.0114(6) -0.0012(6) C10 0.0245(7) 0.0300(7) 0.0331(8) -0.0004(6) 0.0131(6) 0.0054(6) 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' N N 0.0061 0.0033 '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 C4 O4 H2 110.2(10) C2 O3 H1 103.1(10) C8 N1 C12 121.74(11) C8 N1 H6 114.7(10) C12 N1 H6 123.5(10) O3 C2 C3 118.23(12) O3 C2 C1 120.96(11) C3 C2 C1 120.81(11) C5 C6 C1 121.88(11) C5 C6 H5 119.1 C1 C6 H5 119.1 C6 C1 C2 117.72(11) C6 C1 C7 121.67(11) C2 C1 C7 120.61(11) O4 C4 C3 117.81(11) O4 C4 C5 121.80(12) C3 C4 C5 120.40(11) N1 C12 C11 120.41(12) N1 C12 H11 119.8 C11 C12 H11 119.8 C6 C5 C4 119.22(11) C6 C5 H4 120.4 C4 C5 H4 120.4 C8 C9 C10 119.02(12) C8 C9 H8 120.5 C10 C9 H8 120.5 C4 C3 C2 119.94(12) C4 C3 H3 120 C2 C3 H3 120 O2 C7 O1 121.56(11) O2 C7 C1 119.15(12) O1 C7 C1 119.29(11) C12 C11 C10 118.63(12) C12 C11 H10 120.7 C10 C11 H10 120.7 N1 C8 C9 120.35(12) N1 C8 H7 119.8 C9 C8 H7 119.8 C9 C10 C11 119.84(12) C9 C10 H9 120.1 C11 C10 H9 120.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C7 1.2744(16) O4 C4 1.3576(15) O4 H2 0.947(18) O2 C7 1.2617(15) O3 C2 1.3552(15) O3 H1 0.976(19) N1 C8 1.3342(17) N1 C12 1.3380(17) N1 H6 0.953(17) C2 C3 1.3863(18) C2 C1 1.4078(18) C6 C5 1.3772(17) C6 C1 1.3978(17) C6 H5 0.95 C1 C7 1.4824(17) C4 C3 1.3825(18) C4 C5 1.3966(18) C12 C11 1.3712(19) C12 H11 0.95 C5 H4 0.95 C9 C8 1.3694(19) C9 C10 1.3802(19) C9 H8 0.95 C3 H3 0.95 C11 C10 1.3866(19) C11 H10 0.95 C8 H7 0.95 C10 H9 0.95 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 O4 H2 O1 0.947(18) 1.724(18) 2.6653(13) 172.0(16) 2 O3 H1 O2 0.976(19) 1.611(19) 2.5293(13) 155.0(16) . 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 C5 C6 C1 C2 0.66(18) C5 C6 C1 C7 179.91(11) O3 C2 C1 C6 178.30(11) C3 C2 C1 C6 -1.48(17) O3 C2 C1 C7 -0.96(18) C3 C2 C1 C7 179.26(11) C8 N1 C12 C11 -0.14(19) C1 C6 C5 C4 0.82(18) O4 C4 C5 C6 178.86(11) C3 C4 C5 C6 -1.53(18) O4 C4 C3 C2 -179.65(11) C5 C4 C3 C2 0.73(19) O3 C2 C3 C4 -178.98(11) C1 C2 C3 C4 0.80(19) C6 C1 C7 O2 -177.66(11) C2 C1 C7 O2 1.57(17) C6 C1 C7 O1 2.15(17) C2 C1 C7 O1 -178.61(11) N1 C12 C11 C10 0.0(2) C12 N1 C8 C9 0.30(19) C10 C9 C8 N1 -0.3(2) C8 C9 C10 C11 0.2(2) C12 C11 C10 C9 -0.1(2)