#------------------------------------------------------------------------------ #$Date: 2025-08-23 00:36:08 +0100 (Sat, 23 Aug 2025) $ #$Revision: 301880 $ #$URL: svn://www.crystallography.net/cod/cif/8/00/01/8000128.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_8000128 loop_ _publ_author_name 'Ono, Yuki' 'Furuta, Hiroyuki' _publ_section_title ; 2-Picolinoylpyrrole: A New Entry to Metal-complexing Agent ; _journal_issue 7 _journal_name_full 'Chemistry Letters' _journal_page_first 750 _journal_paper_doi 10.1246/cl.2006.750 _journal_volume 35 _journal_year 2006 _chemical_formula_sum 'C10 H8 N2 O' _chemical_formula_weight 172.18 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 95.8120(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.9609(4) _cell_length_b 13.1442(8) _cell_length_c 10.6141(7) _cell_measurement_reflns_used 3535 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.41 _cell_measurement_theta_min 2.47 _cell_volume 827.35(9) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 8.366 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _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 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 4595 _diffrn_reflns_theta_full 24.71 _diffrn_reflns_theta_max 24.71 _diffrn_reflns_theta_min 2.47 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 270 _diffrn_standards_number 112 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 0.9682 _exptl_absorpt_correction_T_min 0.9506 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS;Sheldrick, 1996' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 360 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.189 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 118 _refine_ls_number_reflns 1406 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0327 _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^)+(0.0458P)^2^+0.2696P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.0882 _reflns_number_gt 1311 _reflns_number_total 1406 _reflns_threshold_expression >2sigma(I) _cod_data_source_file 35-750sup2.cif _cod_data_source_block p21n _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 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 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 ; _cod_original_sg_symbol_H-M P2(1)/n _cod_database_code 8000128 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags C1 C 0.4945(2) 0.57168(10) 0.20386(12) 0.0254(3) Uani 1 1 d . H2 H 0.6298 0.6088 0.1980 0.030 Uiso 1 1 calc R C2 C 0.3309(2) 0.55331(10) 0.10566(12) 0.0266(3) Uani 1 1 d . H3A H 0.3319 0.5758 0.0206 0.032 Uiso 1 1 calc R C3 C 0.1630(2) 0.49548(10) 0.15418(12) 0.0240(3) Uani 1 1 d . H4 H 0.0289 0.4712 0.1079 0.029 Uiso 1 1 calc R C4 C 0.2271(2) 0.47975(9) 0.28236(12) 0.0210(3) Uani 1 1 d . C5 C 0.1294(2) 0.42573(9) 0.38205(11) 0.0210(3) Uani 1 1 d . C6 C -0.0856(2) 0.36619(9) 0.35462(12) 0.0215(3) Uani 1 1 d . C7 C -0.1942(2) 0.33086(9) 0.45596(12) 0.0234(3) Uani 1 1 d . H5 H -0.1348 0.3453 0.5405 0.028 Uiso 1 1 calc R C8 C -0.3901(2) 0.27436(10) 0.43210(13) 0.0271(3) Uani 1 1 d . H6 H -0.4658 0.2481 0.4997 0.033 Uiso 1 1 calc R C9 C -0.4726(2) 0.25715(10) 0.30767(13) 0.0288(3) Uani 1 1 d . H7 H -0.6075 0.2194 0.2877 0.035 Uiso 1 1 calc R C10 C -0.3548(2) 0.29600(11) 0.21281(13) 0.0312(3) Uani 1 1 d . H8 H -0.4136 0.2842 0.1275 0.037 Uiso 1 1 calc R N1 N 0.43163(17) 0.52846(8) 0.30953(10) 0.0233(3) Uani 1 1 d . H1 H 0.5090 0.5308 0.3846 0.028 Uiso 1 1 calc R N2 N -0.16361(18) 0.34905(8) 0.23361(10) 0.0277(3) Uani 1 1 d . O1 O 0.22172(14) 0.42654(7) 0.49188(8) 0.0247(2) Uani 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0223(7) 0.0259(7) 0.0286(7) -0.0004(5) 0.0059(5) -0.0015(5) C2 0.0296(7) 0.0287(7) 0.0215(6) 0.0029(5) 0.0028(5) 0.0001(5) C3 0.0227(7) 0.0254(7) 0.0227(7) -0.0007(5) -0.0028(5) -0.0005(5) C4 0.0187(6) 0.0211(6) 0.0227(7) -0.0024(5) -0.0008(5) 0.0008(5) C5 0.0199(6) 0.0212(6) 0.0212(6) -0.0016(5) -0.0005(5) 0.0045(5) C6 0.0212(6) 0.0187(6) 0.0240(7) 0.0013(5) -0.0007(5) 0.0032(5) C7 0.0229(7) 0.0221(6) 0.0247(7) 0.0020(5) 0.0002(5) 0.0056(5) C8 0.0244(7) 0.0232(7) 0.0348(8) 0.0055(5) 0.0075(5) 0.0032(5) C9 0.0226(7) 0.0225(7) 0.0405(8) 0.0011(6) -0.0013(6) -0.0017(5) C10 0.0317(8) 0.0294(7) 0.0308(8) 0.0005(6) -0.0057(6) -0.0080(6) N1 0.0204(6) 0.0270(6) 0.0217(6) -0.0021(4) -0.0012(4) -0.0011(4) N2 0.0287(6) 0.0277(6) 0.0257(6) 0.0010(5) -0.0028(5) -0.0071(5) O1 0.0222(5) 0.0311(5) 0.0199(5) 0.0001(4) -0.0016(4) 0.0008(4) 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 N1 C1 C2 108.78(11) C1 C2 C3 107.22(12) C4 C3 C2 107.80(11) N1 C4 C3 106.52(11) N1 C4 C5 119.16(11) C3 C4 C5 134.31(12) O1 C5 C4 120.80(11) O1 C5 C6 118.38(11) C4 C5 C6 120.81(11) N2 C6 C7 122.82(11) N2 C6 C5 118.62(11) C7 C6 C5 118.57(11) C8 C7 C6 119.17(12) C9 C8 C7 118.35(12) C8 C9 C10 118.56(12) N2 C10 C9 124.10(13) C1 N1 C4 109.67(11) C10 N2 C6 116.98(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.3440(17) C1 C2 1.3749(19) C2 C3 1.3960(19) C3 C4 1.3908(18) C4 N1 1.3817(16) C4 C5 1.4447(18) C5 O1 1.2376(15) C5 C6 1.5050(17) C6 N2 1.3400(16) C6 C7 1.3901(18) C7 C8 1.3856(18) C8 C9 1.3805(19) C9 C10 1.382(2) C10 N2 1.3354(17) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 3533079