#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2012491.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_2012491 loop_ _publ_author_name 'Sabino, J. R.' 'da Silva, C. H. T. P.' 'Yonashiro, M.' _publ_section_title ; 6-Aminopyridine-3-thiol ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o78 _journal_page_last o79 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C5 H6 N2 S' _chemical_formula_sum 'C5 H6 N2 S' _chemical_formula_weight 126.18 _chemical_name_systematic ; 2-amino-5-thiolpyridine ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 104.753(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.3430(3) _cell_length_b 5.7560(3) _cell_length_c 7.2730(6) _cell_measurement_reflns_used 2311 _cell_measurement_temperature 100 _cell_measurement_theta_max 27.49 _cell_measurement_theta_min 3.16 _cell_volume 540.17(5) _computing_cell_refinement COLLECT _computing_data_collection 'COLLECT (Nonius, 1997-2000)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method oscillation _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .036 _diffrn_reflns_av_sigmaI/netI .042 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 2311 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 3.16 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .468 _exptl_absorpt_correction_type none _exptl_crystal_colour 'light orange' _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 264 _exptl_crystal_size_max .07 _exptl_crystal_size_mid .05 _exptl_crystal_size_min .03 _refine_diff_density_max .32 _refine_diff_density_min -.23 _refine_ls_extinction_coef .031(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 86 _refine_ls_number_reflns 1240 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all .050 _refine_ls_R_factor_gt .036 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0563P)^2^+0.08P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .091 _refine_ls_wR_factor_ref .100 _reflns_number_gt 1001 _reflns_number_total 1240 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file da1211.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P21/c _cod_database_code 2012491 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_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol C1 .22172(14) .2029(3) .0894(3) .0224(4) Uani d . 1 C H1 .2148 .3508 .1430 .027 Uiso calc R 1 H C2 .31823(14) .1363(3) .0713(3) .0221(4) Uani d . 1 C C3 .32983(14) -.0804(3) -.0062(2) .0232(4) Uani d . 1 C H3 .3956 -.1312 -.0181 .028 Uiso calc R 1 H C4 .24367(15) -.2184(3) -.0650(3) .0239(4) Uani d . 1 C H4 .2490 -.3664 -.1196 .029 Uiso calc R 1 H C5 .14730(14) -.1396(3) -.0438(3) .0236(4) Uani d . 1 C N1 .13713(12) .0681(3) .0346(2) .0239(4) Uani d . 1 N N2 .06043(13) -.2746(3) -.0966(3) .0320(4) Uani d D 1 N H2A .0000(11) -.214(5) -.078(3) .045(7) Uiso d D 1 H H2B .062(2) -.408(3) -.166(3) .054(8) Uiso d D 1 H S1 .42348(3) .32395(8) .13957(6) .0230(2) Uani d . 1 S 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 C1 .0223(9) .0205(9) .0239(9) .0012(7) .0053(7) .0020(7) C2 .0212(9) .0233(9) .0215(9) -.0025(7) .0050(7) .0017(7) C3 .0239(9) .0223(9) .0245(9) .0033(7) .0084(7) .0033(7) C4 .0281(9) .0209(9) .0231(9) .0026(8) .0074(7) .0003(8) C5 .0234(9) .0248(10) .0221(8) -.0011(7) .0050(7) .0013(7) N1 .0222(8) .0225(8) .0272(8) -.0002(6) .0067(6) -.0010(6) N2 .0263(9) .0289(10) .0421(10) -.0051(7) .0111(8) -.0093(8) S1 .0189(3) .0222(3) .0276(3) -.00251(16) .00561(18) -.00215(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 '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 C1 C2 C3 119.28(17) y C1 C2 S1 120.31(15) y C3 C2 S1 120.39(14) y N1 C5 N2 117.01(17) y N1 C5 C4 121.72(17) y N2 C5 C4 121.23(18) y C5 N2 H2A 117.0(17) y C5 N2 H2B 119.5(17) y H2A N2 H2B 123(2) y N1 C1 C2 122.97(18) ? N1 C1 H1 118.5 ? C2 C1 H1 118.5 ? C4 C3 C2 118.25(17) ? C4 C3 H3 120.9 ? C2 C3 H3 120.9 ? C3 C4 C5 119.66(17) ? C3 C4 H4 120.2 ? C5 C4 H4 120.2 ? C1 N1 C5 118.09(16) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 N1 1.344(2) y C1 C2 1.382(2) y C2 C3 1.394(3) y C2 S1 1.7406(18) y C3 C4 1.373(3) y C4 C5 1.408(3) y C5 N1 1.346(3) y C5 N2 1.367(3) y C1 H1 .9500 ? C3 H3 .9500 ? C4 H4 .9500 ? N2 H2A .920(5) ? N2 H2B .921(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H2A N1 3 .920(5) 2.108(6) 3.028(2) 179(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 N1 C1 C2 C3 -.3(3) N1 C1 C2 S1 178.24(14) C1 C2 C3 C4 1.1(3) S1 C2 C3 C4 -177.42(14) C2 C3 C4 C5 -.6(3) C3 C4 C5 N1 -.6(3) C3 C4 C5 N2 -178.46(18) C2 C1 N1 C5 -1.0(3) N2 C5 N1 C1 179.37(18) C4 C5 N1 C1 1.5(3)