#------------------------------------------------------------------------------ #$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201979 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/23/02/2230214.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_2230214 loop_ _publ_author_name 'Hu, Zhi-Nan' 'Yang, Hui-Bin' 'Luo, Huan' 'Li, Bin' _publ_section_title ; 3-Chloropyridin-2-amine ; _journal_coeditor_code ZS2107 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1138 _journal_paper_doi 10.1107/S1600536811013432 _journal_volume 67 _journal_year 2011 _chemical_formula_iupac 'C5 H5 Cl N2' _chemical_formula_moiety 'C5 H5 Cl N2' _chemical_formula_sum 'C5 H5 Cl N2' _chemical_formula_weight 128.56 _chemical_name_systematic ; 3-Chloropyridin-2-amine ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.581(12) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.149(8) _cell_length_b 5.453(4) _cell_length_c 9.844(7) _cell_measurement_reflns_used 1473 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.19 _cell_measurement_theta_min 3.66 _cell_volume 598.4(7) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _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 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 2778 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 1.83 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.520 _exptl_absorpt_correction_T_max 0.8942 _exptl_absorpt_correction_T_min 0.8269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.568 _refine_diff_density_min -0.312 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 73 _refine_ls_number_reflns 1057 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0591 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1147P)^2^+0.2179P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1604 _refine_ls_wR_factor_ref 0.1815 _reflns_number_gt 867 _reflns_number_total 1057 _reflns_threshold_expression I>2\s(I) _cod_data_source_file zs2107.cif _cod_data_source_block I _cod_original_cell_volume 598.5(7) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2230214 _cod_database_fobs_code 2230214 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_type_symbol _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_disorder_assembly _atom_site_disorder_group Cl Cl1 0.89884(8) 0.20978(18) 0.46576(10) 0.0821(5) Uani d . 1 . . N N1 0.6085(2) 0.5920(5) 0.3676(2) 0.0597(7) Uani d . 1 . . N N2 0.6357(3) 0.2720(5) 0.5172(3) 0.0716(8) Uani d . 1 . . H H2A 0.5613 0.2836 0.5385 0.086 Uiso calc R 1 . . H H2B 0.6804 0.1628 0.5553 0.086 Uiso calc R 1 . . C C1 0.6825(2) 0.4252(5) 0.4237(3) 0.0505(7) Uani d . 1 . . C C2 0.8035(2) 0.4167(5) 0.3855(3) 0.0535(7) Uani d . 1 . . C C3 0.8465(3) 0.5728(6) 0.2897(3) 0.0635(8) Uani d . 1 . . H H3 0.9266 0.5667 0.2645 0.076 Uiso calc R 1 . . C C4 0.7692(3) 0.7404(7) 0.2306(3) 0.0725(10) Uani d . 1 . . H H4 0.7955 0.8481 0.1640 0.087 Uiso calc R 1 . . C C5 0.6520(3) 0.7431(6) 0.2735(4) 0.0698(9) Uani d . 1 . . H H5 0.6000 0.8571 0.2345 0.084 Uiso calc R 1 . . 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 Cl1 0.0717(7) 0.0833(7) 0.0913(8) 0.0322(4) 0.0101(5) 0.0145(4) N1 0.0545(13) 0.0566(14) 0.0681(15) 0.0068(11) 0.0018(10) 0.0047(11) N2 0.0674(16) 0.0602(16) 0.088(2) 0.0131(12) 0.0194(14) 0.0196(13) C1 0.0572(14) 0.0411(13) 0.0533(15) 0.0036(11) 0.0026(11) -0.0039(11) C2 0.0558(15) 0.0510(15) 0.0537(15) 0.0099(11) 0.0019(11) -0.0057(12) C3 0.0561(15) 0.076(2) 0.0583(17) -0.0019(14) 0.0070(13) 0.0002(14) C4 0.077(2) 0.074(2) 0.067(2) -0.0049(15) 0.0047(17) 0.0178(15) C5 0.073(2) 0.0617(19) 0.074(2) 0.0057(14) -0.0054(16) 0.0155(15) 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' Cl Cl 0.1484 0.1585 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 N1 C1 . . 118.5(3) ? C1 N2 H2A . . 120.0 ? C1 N2 H2B . . 120.0 ? H2A N2 H2B . . 120.0 ? N1 C1 N2 . . 117.3(3) ? N1 C1 C2 . . 120.0(2) ? N2 C1 C2 . . 122.7(2) ? C3 C2 C1 . . 120.7(3) ? C3 C2 Cl1 . . 120.2(2) ? C1 C2 Cl1 . . 119.0(2) ? C2 C3 C4 . . 118.9(3) ? C2 C3 H3 . . 120.6 ? C4 C3 H3 . . 120.6 ? C5 C4 C3 . . 117.9(3) ? C5 C4 H4 . . 121.0 ? C3 C4 H4 . . 121.0 ? N1 C5 C4 . . 124.0(3) ? N1 C5 H5 . . 118.0 ? C4 C5 H5 . . 118.0 ? 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 Cl1 C2 . 1.735(3) ? N1 C5 . 1.334(4) ? N1 C1 . 1.344(4) ? N2 C1 . 1.351(4) ? N2 H2A . 0.8600 ? N2 H2B . 0.8600 ? C1 C2 . 1.405(4) ? C2 C3 . 1.361(4) ? C3 C4 . 1.380(4) ? C3 H3 . 0.9300 ? C4 C5 . 1.378(5) ? C4 H4 . 0.9300 ? C5 H5 . 0.9300 ? 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 _geom_hbond_publ_flag N2 H2A N1 3_666 0.86 2.22 3.051(5) 162 yes N2 H2B Cl1 . 0.86 2.61 3.001(4) 109 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C5 N1 C1 N2 . . . . -179.0(3) ? C5 N1 C1 C2 . . . . 1.5(4) ? N1 C1 C2 C3 . . . . -1.3(4) ? N2 C1 C2 C3 . . . . 179.2(3) ? N1 C1 C2 Cl1 . . . . 176.8(2) ? N2 C1 C2 Cl1 . . . . -2.6(4) ? C1 C2 C3 C4 . . . . 0.1(5) ? Cl1 C2 C3 C4 . . . . -178.0(2) ? C2 C3 C4 C5 . . . . 0.9(5) ? C1 N1 C5 C4 . . . . -0.6(5) ? C3 C4 C5 N1 . . . . -0.7(5) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 604083