#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/20/2212063.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_2212063 loop_ _publ_author_name 'Rubin-Preminger, Janice M.' 'Englert, Ulli' _publ_section_title ; 3,4-Diaminopyridine ; _journal_coeditor_code BT2244 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o757 _journal_page_last o758 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C5 H7 N3' _chemical_formula_moiety 'C5 H7 N3' _chemical_formula_sum 'C5 H7 N3' _chemical_formula_weight 109.13 _chemical_melting_point 217.0(10) _chemical_name_common 3,4-diaminopyridine _chemical_name_systematic ; 3,4-diaminopyridine ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.5815(18) _cell_length_b 7.352(2) _cell_length_c 12.579(4) _cell_measurement_reflns_used 579 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 21.63 _cell_measurement_theta_min 3.15 _cell_volume 516.2(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \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 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5342 _diffrn_reflns_theta_full 25.88 _diffrn_reflns_theta_max 25.88 _diffrn_reflns_theta_min 3.21 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_description platelet _exptl_crystal_F_000 232 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _refine_diff_density_max .182 _refine_diff_density_min -.131 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 73 _refine_ls_number_reflns 614 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0363 _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^)+(0.03P)^2^+0.2P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0786 _refine_ls_wR_factor_ref 0.0806 _reflns_number_gt 562 _reflns_number_total 614 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt2244.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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: '_chemical_melting_point' value '216-218' was changed to '217.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '216-218' was changed to '217.0(10)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2212063 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 N N1 0.3611(4) -0.0405(3) -0.07697(14) 0.0174(5) Uani d . 1 N N2 0.1059(4) -0.1199(3) 0.19043(15) 0.0179(5) Uani d . 1 H H2A -0.0323 -0.1671 0.1660 0.021 Uiso d R 1 H H2B 0.0860 -0.0457 0.2466 0.021 Uiso d R 1 N N3 0.5142(4) 0.0869(3) 0.24078(16) 0.0232(5) Uani d . 1 H H3A 0.3981 0.0706 0.2895 0.028 Uiso d R 1 H H3B 0.6313 0.1691 0.2511 0.028 Uiso d R 1 C C2 0.2151(4) -0.0877(3) 0.00339(18) 0.0162(5) Uani d . 1 H H2 0.0721 -0.1508 -0.0144 0.019 Uiso calc R 1 C C3 0.2559(4) -0.0521(3) 0.10995(17) 0.0138(5) Uani d . 1 C C4 0.4643(4) 0.0466(3) 0.13767(18) 0.0165(5) Uani d . 1 C C5 0.6169(4) 0.0952(3) 0.05459(18) 0.0175(5) Uani d . 1 H H5 0.7602 0.1602 0.0693 0.021 Uiso calc R 1 C C6 0.5607(4) 0.0493(3) -0.04904(18) 0.0182(5) Uani d . 1 H H6 0.6696 0.0833 -0.1036 0.022 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 N1 0.0197(11) 0.0162(9) 0.0163(10) 0.0012(9) -0.0006(8) 0.0005(8) N2 0.0183(10) 0.0209(10) 0.0143(10) -0.0038(8) 0.0006(9) -0.0021(8) N3 0.0244(11) 0.0277(11) 0.0174(10) -0.0095(10) 0.0000(9) -0.0030(9) C2 0.0145(12) 0.0139(11) 0.0202(11) 0.0005(9) -0.0033(10) 0.0007(9) C3 0.0139(11) 0.0112(10) 0.0164(11) 0.0038(10) 0.0013(10) 0.0021(9) C4 0.0204(12) 0.0113(10) 0.0179(11) 0.0024(10) -0.0020(10) -0.0004(9) C5 0.0140(11) 0.0151(11) 0.0233(12) -0.0004(10) -0.0006(11) 0.0000(10) C6 0.0168(13) 0.0188(12) 0.0190(12) 0.0000(10) 0.0038(10) 0.0024(11) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C6 N1 C2 115.69(19) C3 N2 H2A 113.6 C3 N2 H2B 115.1 H2A N2 H2B 113.4 C4 N3 H3A 118.3 C4 N3 H3B 115.7 H3A N3 H3B 120.9 N1 C2 C3 125.4(2) N1 C2 H2 117.3 C3 C2 H2 117.3 C2 C3 N2 122.2(2) C2 C3 C4 118.1(2) N2 C3 C4 119.63(19) N3 C4 C5 122.3(2) N3 C4 C3 121.0(2) C5 C4 C3 116.7(2) C6 C5 C4 120.4(2) C6 C5 H5 119.8 C4 C5 H5 119.8 N1 C6 C5 123.7(2) N1 C6 H6 118.1 C5 C6 H6 118.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C6 1.342(3) N1 C2 1.344(3) N2 C3 1.405(3) N2 H2A 0.9000 N2 H2B 0.9000 N3 C4 1.359(3) N3 H3A 0.9000 N3 H3B 0.9000 C2 C3 1.385(3) C2 H2 0.9500 C3 C4 1.415(3) C4 C5 1.395(3) C5 C6 1.383(3) C5 H5 0.9500 C6 H6 0.9500 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 4_445 .90 2.50 3.184(3) 134 yes N2 H2B N1 2_555 .90 2.33 3.160(3) 154 yes N3 H3A N2 . .90 2.48 2.812(3) 102 yes N3 H3A N1 2_555 .90 2.23 3.124(3) 174 yes N3 H3B N2 3_655 .90 2.26 3.145(3) 169 yes 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 C6 N1 C2 C3 -0.4(3) N1 C2 C3 N2 -174.1(2) N1 C2 C3 C4 1.9(3) C2 C3 C4 N3 179.7(2) N2 C3 C4 N3 -4.2(3) C2 C3 C4 C5 -2.0(3) N2 C3 C4 C5 174.1(2) N3 C4 C5 C6 179.1(2) C3 C4 C5 C6 0.8(3) C2 N1 C6 C5 -1.0(3) C4 C5 C6 N1 0.7(4) _cod_database_fobs_code 2212063