#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013305.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_2013305 loop_ _publ_author_name 'Noland, Wayland E.' 'Cole, Kevin P.' 'Britton, Doyle' _publ_section_title ; Five (1H-pyrrol-2-yl)pyridines ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o263 _journal_page_last o267 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C9 H8 N2' _chemical_formula_moiety 'C9 H8 N2' _chemical_formula_sum 'C9 H8 N2' _chemical_formula_weight 144.17 _chemical_name_systematic ; 4-(1H-pyrrol-2-yl)pyridine ; _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 'SHELXTL plus manual additions' _cell_angle_alpha 90.00 _cell_angle_beta 103.760(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 15.139(4) _cell_length_b 5.4945(14) _cell_length_c 18.736(5) _cell_measurement_reflns_used 2651 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.8 _cell_measurement_theta_min 2.2 _cell_volume 1513.8(7) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Siemens SMART 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 0.049 _diffrn_reflns_av_sigmaI/netI 0.047 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 14309 _diffrn_reflns_theta_full 27.51 _diffrn_reflns_theta_max 27.51 _diffrn_reflns_theta_min 1.38 _diffrn_standards_decay_% 'less than 1' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996; Blessing, 1995)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.21 _refine_diff_density_min -0.17 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 207 _refine_ls_number_reflns 3452 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.03 _refine_ls_R_factor_all 0.079 _refine_ls_R_factor_gt 0.047 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.039P)^2^+0.333P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.098 _reflns_number_gt 2385 _reflns_number_total 3452 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file kb1000.cif _[local]_cod_data_source_block IIIB _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2013305 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 N1A 0.27576(9) 0.3961(3) 0.53606(7) 0.0384(3) Uani d . 1 N C2A 0.29091(10) 0.1884(3) 0.50396(8) 0.0345(4) Uani d . 1 C H2A 0.3516 0.1294 0.5137 0.041 Uiso calc R 1 H C3A 0.22412(10) 0.0537(3) 0.45747(8) 0.0323(4) Uani d . 1 C H3A 0.2395 -0.0919 0.4359 0.039 Uiso calc R 1 H C4A 0.13355(10) 0.1330(3) 0.44233(8) 0.0313(3) Uani d . 1 C C5A 0.11799(11) 0.3500(3) 0.47555(9) 0.0396(4) Uani d . 1 C H5A 0.0581 0.4138 0.4671 0.047 Uiso calc R 1 H C6A 0.18896(11) 0.4721(3) 0.52049(9) 0.0428(4) Uani d . 1 C H6A 0.1758 0.6202 0.5420 0.051 Uiso calc R 1 H C7A 0.05897(10) -0.0024(3) 0.39618(8) 0.0333(4) Uani d . 1 C N8A 0.07100(9) -0.1964(3) 0.35351(7) 0.0346(3) Uani d . 1 N H8A 0.1266(12) -0.251(3) 0.3465(9) 0.049(5) Uiso d . 1 H C9A -0.01126(11) -0.2884(3) 0.31821(9) 0.0410(4) Uani d . 1 C H9A -0.0210 -0.4226 0.2853 0.049 Uiso calc R 1 H C10A -0.07738(11) -0.1543(4) 0.33842(10) 0.0492(5) Uani d . 1 C H10A -0.1412 -0.1788 0.3224 0.059 Uiso calc R 1 H C11A -0.03390(11) 0.0253(4) 0.38697(10) 0.0486(5) Uani d . 1 C H11A -0.0630 0.1457 0.4097 0.058 Uiso calc R 1 H N1B 0.23424(9) 0.8359(3) 0.80902(7) 0.0379(3) Uani d . 1 N C2B 0.23462(11) 0.6726(3) 0.75637(9) 0.0394(4) Uani d . 1 C H2B 0.1943 0.5381 0.7524 0.047 Uiso calc R 1 H C3B 0.28941(10) 0.6856(3) 0.70726(8) 0.0349(4) Uani d . 1 C H3B 0.2865 0.5623 0.6712 0.042 Uiso calc R 1 H C4B 0.34898(9) 0.8809(3) 0.71097(8) 0.0285(3) Uani d . 1 C C5B 0.34858(10) 1.0534(3) 0.76572(9) 0.0347(4) Uani d . 1 C H5B 0.3875 1.1911 0.7707 0.042 Uiso calc R 1 H C6B 0.29178(10) 1.0235(3) 0.81231(9) 0.0380(4) Uani d . 1 C H6B 0.2933 1.1432 0.8492 0.046 Uiso calc R 1 H C7B 0.41214(9) 0.9031(3) 0.66349(8) 0.0289(3) Uani d . 1 C N8B 0.41667(9) 0.7352(3) 0.60987(7) 0.0335(3) Uani d . 1 N H8B 0.3747(12) 0.614(4) 0.5915(10) 0.057(6) Uiso d . 1 H C9B 0.48412(11) 0.8000(3) 0.57681(9) 0.0387(4) Uani d . 1 C H9B 0.5004 0.7153 0.5376 0.046 Uiso calc R 1 H C10B 0.52452(10) 1.0078(3) 0.60954(9) 0.0385(4) Uani d . 1 C H10B 0.5739 1.0918 0.5976 0.046 Uiso calc R 1 H C11B 0.47941(10) 1.0736(3) 0.66395(8) 0.0342(4) Uani d . 1 C H11B 0.4927 1.2109 0.6955 0.041 Uiso calc R 1 H 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 N1A 0.0398(8) 0.0369(8) 0.0374(7) -0.0027(6) 0.0068(6) -0.0036(6) C2A 0.0307(8) 0.0378(9) 0.0341(8) 0.0008(7) 0.0064(6) -0.0003(7) C3A 0.0326(8) 0.0335(9) 0.0312(8) 0.0010(7) 0.0081(6) -0.0028(7) C4A 0.0317(8) 0.0362(9) 0.0273(7) -0.0002(7) 0.0098(6) 0.0019(7) C5A 0.0330(8) 0.0416(10) 0.0435(9) 0.0058(7) 0.0080(7) -0.0036(8) C6A 0.0464(10) 0.0359(10) 0.0465(10) 0.0016(8) 0.0120(8) -0.0081(8) C7A 0.0310(8) 0.0375(9) 0.0320(8) -0.0011(7) 0.0088(6) -0.0022(7) N8A 0.0307(7) 0.0407(8) 0.0322(7) -0.0007(6) 0.0075(6) -0.0034(6) C9A 0.0370(9) 0.0462(10) 0.0368(9) -0.0079(8) 0.0030(7) -0.0057(8) C10A 0.0294(8) 0.0605(12) 0.0553(11) -0.0045(8) 0.0053(8) -0.0081(10) C11A 0.0317(9) 0.0568(12) 0.0585(11) 0.0004(8) 0.0129(8) -0.0153(10) N1B 0.0360(7) 0.0435(8) 0.0352(7) 0.0003(6) 0.0106(6) 0.0025(7) C2B 0.0361(8) 0.0404(10) 0.0416(9) -0.0105(7) 0.0088(7) 0.0001(8) C3B 0.0370(8) 0.0338(9) 0.0334(8) -0.0064(7) 0.0077(7) -0.0058(7) C4B 0.0260(7) 0.0302(8) 0.0270(7) 0.0020(6) 0.0018(6) 0.0034(6) C5B 0.0341(8) 0.0321(9) 0.0375(9) -0.0040(7) 0.0078(7) -0.0034(7) C6B 0.0397(9) 0.0383(10) 0.0361(9) -0.0002(7) 0.0095(7) -0.0043(7) C7B 0.0293(7) 0.0284(8) 0.0264(7) 0.0003(6) 0.0016(6) 0.0006(6) N8B 0.0337(7) 0.0346(8) 0.0320(7) -0.0011(6) 0.0073(6) -0.0017(6) C9B 0.0358(8) 0.0487(11) 0.0335(8) 0.0060(8) 0.0121(7) 0.0030(8) C10B 0.0301(8) 0.0502(11) 0.0351(9) -0.0033(7) 0.0072(7) 0.0075(8) C11B 0.0302(8) 0.0382(9) 0.0311(8) -0.0054(7) 0.0014(6) 0.0017(7) 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 C2A N1A C6A 115.60(14) N1A C2A C3A 124.30(14) N1A C2A H2A 117.8 C3A C2A H2A 117.8 C2A C3A C4A 119.64(15) C2A C3A H3A 120.2 C4A C3A H3A 120.2 C5A C4A C3A 115.95(14) C5A C4A C7A 120.99(14) C3A C4A C7A 123.05(14) C6A C5A C4A 120.18(15) C6A C5A H5A 119.9 C4A C5A H5A 119.9 N1A C6A C5A 124.33(16) N1A C6A H6A 117.8 C5A C6A H6A 117.8 N8A C7A C11A 106.56(14) N8A C7A C4A 123.58(14) C11A C7A C4A 129.83(15) C9A N8A C7A 109.84(14) C9A N8A H8A 124.4(11) C7A N8A H8A 125.6(11) N8A C9A C10A 108.11(15) N8A C9A H9A 125.9 C10A C9A H9A 125.9 C9A C10A C11A 107.37(15) C9A C10A H10A 126.3 C11A C10A H10A 126.3 C7A C11A C10A 108.12(15) C7A C11A H11A 125.9 C10A C11A H11A 125.9 C2B N1B C6B 115.69(14) N1B C2B C3B 124.57(15) N1B C2B H2B 117.7 C3B C2B H2B 117.7 C2B C3B C4B 119.44(15) C2B C3B H3B 120.3 C4B C3B H3B 120.3 C3B C4B C5B 116.31(14) C3B C4B C7B 123.02(14) C5B C4B C7B 120.61(14) C6B C5B C4B 119.88(15) C6B C5B H5B 120.1 C4B C5B H5B 120.1 N1B C6B C5B 124.11(15) N1B C6B H6B 117.9 C5B C6B H6B 117.9 N8B C7B C11B 107.10(13) N8B C7B C4B 122.87(14) C11B C7B C4B 129.94(14) C9B N8B C7B 109.24(14) C9B N8B H8B 122.7(12) C7B N8B H8B 127.1(12) N8B C9B C10B 108.52(15) N8B C9B H9B 125.7 C10B C9B H9B 125.7 C9B C10B C11B 107.30(14) C9B C10B H10B 126.3 C11B C10B H10B 126.3 C7B C11B C10B 107.82(14) C7B C11B H11B 126.1 C10B C11B H11B 126.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1A C2A 1.335(2) N1A C6A 1.343(2) C2A C3A 1.382(2) C2A H2A 0.9500 C3A C4A 1.402(2) C3A H3A 0.9500 C4A C5A 1.391(2) C4A C7A 1.453(2) C5A C6A 1.372(2) C5A H5A 0.9500 C6A H6A 0.9500 C7A N8A 1.370(2) C7A C11A 1.384(2) N8A C9A 1.361(2) N8A H8A 0.931(18) C9A C10A 1.367(2) C9A H9A 0.9500 C10A C11A 1.397(2) C10A H10A 0.9500 C11A H11A 0.9500 N1B C2B 1.335(2) N1B C6B 1.341(2) C2B C3B 1.379(2) C2B H2B 0.9500 C3B C4B 1.393(2) C3B H3B 0.9500 C4B C5B 1.398(2) C4B C7B 1.458(2) C5B C6B 1.373(2) C5B H5B 0.9500 C6B H6B 0.9500 C7B N8B 1.377(2) C7B C11B 1.382(2) N8B C9B 1.362(2) N8B H8B 0.929(19) C9B C10B 1.369(2) C9B H9B 0.9500 C10B C11B 1.403(2) C10B H10B 0.9500 C11B H11B 0.9500 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 C6A N1A C2A C3A -0.1(2) N1A C2A C3A C4A -0.7(2) C2A C3A C4A C5A 1.0(2) C2A C3A C4A C7A -177.77(15) C3A C4A C5A C6A -0.5(2) C7A C4A C5A C6A 178.31(15) C2A N1A C6A C5A 0.7(2) C4A C5A C6A N1A -0.4(3) C5A C4A C7A N8A 169.99(15) C3A C4A C7A N8A -11.3(2) C5A C4A C7A C11A -12.1(3) C3A C4A C7A C11A 166.58(17) C11A C7A N8A C9A 0.17(18) C4A C7A N8A C9A 178.48(15) C7A N8A C9A C10A -0.38(19) N8A C9A C10A C11A 0.4(2) N8A C7A C11A C10A 0.1(2) C4A C7A C11A C10A -178.07(17) C9A C10A C11A C7A -0.3(2) C6B N1B C2B C3B 0.4(2) N1B C2B C3B C4B -0.4(3) C2B C3B C4B C5B 0.0(2) C2B C3B C4B C7B 177.12(14) C3B C4B C5B C6B 0.4(2) C7B C4B C5B C6B -176.81(14) C2B N1B C6B C5B 0.1(2) C4B C5B C6B N1B -0.4(2) C3B C4B C7B N8B 1.5(2) C5B C4B C7B N8B 178.50(14) C3B C4B C7B C11B -174.60(15) C5B C4B C7B C11B 2.4(2) C11B C7B N8B C9B -0.78(17) C4B C7B N8B C9B -177.66(13) C7B N8B C9B C10B 0.92(18) N8B C9B C10B C11B -0.68(18) N8B C7B C11B C10B 0.35(17) C4B C7B C11B C10B 176.93(14) C9B C10B C11B C7B 0.20(18)