#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/74/2007450.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_2007450 loop_ _publ_author_name 'Ng, Seik Weng' 'Turnbull, Mark M.' _publ_section_title ; Methylphenylammonium Hydrogen 2,6-Pyridinedicarboxylate at 158K ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1025 _journal_page_last 1027 _journal_paper_doi 10.1107/S0108270198001590 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C7 H10 N 1+ , C7 H4 N O4 1-' _chemical_formula_sum 'C14 H14 N2 O4' _chemical_formula_weight 274.27 _chemical_name_common 'Methylphenylammonium hydrogen dipicolinate' _chemical_name_systematic ; Methylphenylammonium hydrogen 2,6-pyridinecarboxylate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 93.41(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.834(2) _cell_length_b 8.841(2) _cell_length_c 12.889(2) _cell_measurement_reflns_used 21 _cell_measurement_temperature 158(2) _cell_measurement_theta_max 12.5 _cell_measurement_theta_min 4.0 _cell_volume 1346.1(4) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1990)' _computing_data_reduction XSCANS _computing_molecular_graphics 'SHELXTL/PC Sheldrick, 1990b)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990a)' _diffrn_ambient_temperature 158(2) _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_sigmaI/netI 0.134 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2843 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.80 _diffrn_standards_decay_% None _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_meas ? _exptl_crystal_description 'Triangular block' _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.171 _refine_diff_density_min -0.252 _refine_ls_extinction_coef 'Not refined' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.737 _refine_ls_goodness_of_fit_obs 0.955 _refine_ls_hydrogen_treatment ; O- and N-bonded H atoms were located and refined; riding model for the C-bonded H atoms, with U = 1.5U~eq~(C). ; _refine_ls_matrix_type full _refine_ls_number_parameters 193 _refine_ls_number_reflns 2372 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.737 _refine_ls_restrained_S_obs 0.955 _refine_ls_R_factor_all 0.103 _refine_ls_R_factor_obs .042 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0229P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.071 _refine_ls_wR_factor_obs .068 _reflns_number_observed 1167 _reflns_number_total 2372 _reflns_observed_criterion I>2sigma(I) _cod_data_source_file ka1269.cif _cod_data_source_block ka1269 _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: '_exptl_crystal_density_meas' value 'Not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0229P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0229P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2007450 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 .0400(10) .0270(10) .0160(10) -.0060(10) .0000(10) .0030(10) O2 .0430(10) .0280(10) .0180(10) -.0030(10) -.0050(10) -.0030(10) O3 .0380(10) .0220(10) .0190(10) -.0050(10) .0040(10) -.0030(10) O4 .0330(10) .0280(10) .0150(10) -.0010(10) -.0010(10) .0000(10) N1 .0210(10) .0200(10) .0170(10) .0040(10) -.0010(10) -.0020(10) N2 .0260(10) .0210(10) .0210(10) .0020(10) .0010(10) -.0010(10) C1 .032(2) .015(2) .018(2) .006(2) .0030(10) -.0020(10) C2 .019(2) .019(2) .0200(10) .0050(10) .0030(10) .0000(10) C3 .024(2) .019(2) .0190(10) .0010(10) -.0030(10) .0000(10) C4 .020(2) .021(2) .027(2) .0020(10) .0010(10) .0000(10) C5 .022(2) .020(2) .0180(10) .0040(10) -.0030(10) .0040(10) C6 .017(2) .019(2) .0170(10) .0060(10) -.0010(10) .0010(10) C7 .017(2) .025(2) .020(2) .0070(10) -.0020(10) -.0020(10) C8 .019(2) .021(2) .024(2) .0010(10) -.0010(10) -.0040(10) C9 .028(2) .042(2) .034(2) .001(2) -.004(2) .009(2) C10 .031(2) .051(2) .041(2) -.004(2) .007(2) .011(2) C11 .027(2) .039(2) .048(2) -.001(2) .001(2) -.001(2) C12 .030(2) .034(2) .048(2) .006(2) -.005(2) .009(2) C13 .035(2) .032(2) .031(2) .002(2) .001(2) .009(2) C14 .053(2) .020(2) .032(2) .006(2) .007(2) -.0030(10) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .2765(2) -.1182(2) .76950(10) .0274(5) Uani d . 1 . O O2 .4091(2) .0334(2) .84600(10) .0299(5) Uani d . 1 . O O3 .2697(2) -.2125(2) .42170(10) .0262(5) Uani d . 1 . O O4 .3139(2) -.0347(2) .30590(10) .0256(5) Uani d . 1 . O N1 .3298(2) -.0338(2) .5821(2) .0196(5) Uani d . 1 . N N2 .2210(2) -.3428(3) .6210(2) .0223(6) Uani d . 1 . N C1 .3543(2) -.0127(3) .7697(2) .0216(7) Uani d . 1 . C C2 .3704(2) .0506(3) .6629(2) .0193(6) Uani d . 1 . C C3 .4273(2) .1859(3) .6515(2) .0209(7) Uani d . 1 . C C4 .4429(2) .2394(3) .5525(2) .0229(7) Uani d . 1 . C C5 .4014(2) .1541(3) .4686(2) .0200(7) Uani d . 1 . C C6 .3471(2) .0183(3) .4856(2) .0178(6) Uani d . 1 . C C7 .3071(2) -.0825(3) .3959(2) .0204(7) Uani d . 1 . C C8 .1009(2) -.3116(3) .6354(2) .0215(7) Uani d . 1 . C C9 .0496(2) -.3774(3) .7167(2) .0347(8) Uani d . 1 . C C10 -.0644(3) -.3513(4) .7291(2) .0411(9) Uani d . 1 . C C11 -.1257(3) -.2598(3) .6593(2) .0380(8) Uani d . 1 . C C12 -.0734(3) -.1960(3) .5773(2) .0378(8) Uani d . 1 . C C13 .0407(2) -.2209(3) .5647(2) .0324(8) Uani d . 1 . C C14 .2373(3) -.4796(3) .5555(2) .0350(8) Uani d . 1 . C H1 .272(3) -.170(4) .835(3) .100(10) Uiso d . 1 . H H2a .261(3) -.248(4) .587(2) .090(10) Uiso d . 1 . H H2b .261(2) -.360(3) .697(2) .044(9) Uiso d . 1 . H H3 .4553(2) .2411(3) .7108(2) .031 Uiso calc R 1 . H H4 .4811(2) .3323(3) .5423(2) .034 Uiso calc R 1 . H H5 .4100(2) .1886(3) .3998(2) .030 Uiso calc R 1 . H H9 .0919(2) -.4406(3) .7643(2) .052 Uiso calc R 1 . H H10 -.1003(3) -.3963(4) .7854(2) .062 Uiso calc R 1 . H H12 -.1159(3) -.1343(3) .5289(2) .057 Uiso calc R 1 . H H11 -.2037(3) -.2410(3) .6680(2) .057 Uiso calc R 1 . H H13 .0768(2) -.1762(3) .5084(2) .049 Uiso calc R 1 . H H14a .3183(3) -.4959(3) .5481(2) .052 Uiso calc R 1 . H H14b .1991(3) -.4646(3) .4867(2) .052 Uiso calc R 1 . H H14c .2051(3) -.5681(3) .5887(2) .052 Uiso calc R 1 . H 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 0.0000 0.0000 '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 0.0060 '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 _geom_angle_publ_flag C2 N1 C6 117.1(2) yes C8 N2 C14 112.4(2) yes O1 C1 O2 125.5(2) yes O1 C1 C2 112.9(2) yes O2 C1 C2 121.5(3) yes N1 C2 C1 116.2(2) yes N1 C2 C3 123.3(2) yes C1 C2 C3 120.5(2) yes C2 C3 C4 119.1(3) yes C3 C4 C5 118.2(3) yes C4 C5 C6 119.7(2) yes N1 C6 C5 122.5(2) yes N1 C6 C7 116.4(2) yes C5 C6 C7 121.1(2) yes O3 C7 O4 126.1(2) yes O3 C7 C6 115.3(2) yes O4 C7 C6 118.6(3) yes C9 C8 C13 121.1(3) yes C9 C8 N2 119.5(2) yes C13 C8 N2 119.4(3) yes C8 C9 C10 119.7(3) yes C9 C10 C11 119.9(3) yes C12 C11 C10 119.7(3) yes C11 C12 C13 120.7(3) yes C8 C13 C12 118.9(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.310(3) yes O2 C1 . 1.216(3) yes O3 C7 . 1.283(3) yes O4 C7 . 1.242(3) yes N1 C2 . 1.347(3) yes N1 C6 . 1.353(3) yes N2 C8 . 1.470(3) yes N2 C14 . 1.494(3) yes C1 C2 . 1.508(3) yes C2 C3 . 1.384(3) yes C3 C4 . 1.384(3) yes C4 C5 . 1.383(3) yes C5 C6 . 1.385(3) yes C6 C7 . 1.513(3) yes C8 C9 . 1.372(3) yes C8 C13 . 1.379(3) yes C9 C10 . 1.388(4) yes C10 C11 . 1.382(4) yes C11 C12 . 1.377(4) yes C12 C13 . 1.388(4) yes N2 N1 . 3.074(3) no N2 O4 4_556 2.784(3) no N2 O1 . 2.809(3) no N2 O3 . 2.904(3) no O1 O3 4_556 2.472(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139056103