#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/36/2203664.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_2203664 loop_ _publ_author_name 'Leonard F. Lindoy' 'John C. McMurtrie' 'Jason R. Price' _publ_section_title ; 6,6'-Bis(chloromethyl)-2,2'-bipyridine ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o886 _journal_page_last o888 _journal_paper_doi 10.1107/S1600536804008852 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C12 H10 Cl2 N2' _chemical_formula_moiety 'C12 H10 Cl2 N2' _chemical_formula_sum 'C12 H10 Cl2 N2' _chemical_formula_weight 253.12 _chemical_melting_point 430 _chemical_name_systematic ; 6,6'-Bis(chloromethyl)-2,2'-bipyridine ; _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 93.5880(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.7692(11) _cell_length_b 4.3678(4) _cell_length_c 10.8889(10) _cell_measurement_reflns_used 4044 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 28.4 _cell_measurement_theta_min 2.5 _cell_volume 558.65(9) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT and XPREP (Siemens, 1995)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997) and WinGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer (Allen et al., 2004)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.952 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.013 _diffrn_reflns_av_sigmaI/netI 0.012 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5097 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 28.4 _diffrn_reflns_theta_min 1.7 _diffrn_standards_decay_% 0.06 _diffrn_standards_number 80 _exptl_absorpt_coefficient_mu 0.551 _exptl_absorpt_correction_T_max 0.850 _exptl_absorpt_correction_T_min 0.755 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1999)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 260 _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.38 _refine_diff_density_min -0.18 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 73 _refine_ls_number_reflns 1337 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.05 _refine_ls_R_factor_all 0.027 _refine_ls_R_factor_gt 0.025 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0366P)^2^+0.216P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.068 _refine_ls_wR_factor_ref 0.069 _reflns_number_gt 1269 _reflns_number_total 1337 _reflns_threshold_expression I>2\s(I) _cod_data_source_file tk6161.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2203664 _cod_database_fobs_code 2203664 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 0.55441(9) 0.4806(2) 0.96946(9) 0.0195(2) Uani d . 1 C C2 0.56012(9) 0.2944(3) 0.86586(10) 0.0231(2) Uani d . 1 C H2 0.4948 0.1864 0.8337 0.028 Uiso calc R 1 H C3 0.66271(10) 0.2695(3) 0.81069(10) 0.0256(2) Uani d . 1 C H3 0.6689 0.1441 0.7401 0.031 Uiso calc R 1 H C4 0.75625(10) 0.4310(3) 0.86036(10) 0.0244(2) Uani d . 1 C H4 0.8274 0.4207 0.8239 0.029 Uiso calc R 1 H C5 0.74350(9) 0.6086(2) 0.96486(10) 0.0218(2) Uani d . 1 C C6 0.84136(10) 0.7881(3) 1.02271(11) 0.0266(2) Uani d . 1 C H6A 0.8128 0.9819 1.0565 0.032 Uiso calc R 1 H H6B 0.8951 0.8397 0.9594 0.032 Uiso calc R 1 H N1 0.64505(8) 0.6337(2) 1.01938(8) 0.02090(19) Uani d . 1 N Cl1 0.91510(2) 0.57081(7) 1.14489(3) 0.02892(11) Uani d . 1 Cl 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 0.0206(5) 0.0201(5) 0.0174(5) 0.0010(4) -0.0015(4) 0.0029(4) C2 0.0229(5) 0.0259(5) 0.0199(5) 0.0006(4) -0.0028(4) -0.0015(4) C3 0.0272(5) 0.0299(6) 0.0194(5) 0.0037(4) -0.0004(4) -0.0021(4) C4 0.0221(5) 0.0295(6) 0.0218(5) 0.0028(4) 0.0022(4) 0.0034(4) C5 0.0216(5) 0.0218(5) 0.0216(5) -0.0001(4) -0.0014(4) 0.0048(4) C6 0.0232(5) 0.0254(5) 0.0309(6) -0.0031(4) -0.0016(4) 0.0027(4) N1 0.0209(4) 0.0218(4) 0.0197(4) -0.0003(3) -0.0013(3) 0.0016(3) Cl1 0.02356(16) 0.03444(18) 0.02793(17) -0.00080(10) -0.00511(11) -0.00197(10) 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_3 _geom_angle N1 C1 C2 . 122.65(10) N1 C1 C1 3_667 116.45(12) C2 C1 C1 3_667 120.90(12) C3 C2 C1 . 118.89(10) C3 C2 H2 . 120.6 C1 C2 H2 . 120.6 C2 C3 C4 . 118.84(10) C2 C3 H3 . 120.6 C4 C3 H3 . 120.6 C3 C4 C5 . 118.55(10) C3 C4 H4 . 120.7 C5 C4 H4 . 120.7 N1 C5 C4 . 123.24(10) N1 C5 C6 . 115.74(10) C4 C5 C6 . 121.01(10) C5 C6 Cl1 . 110.80(8) C5 C6 H6A . 109.5 Cl1 C6 H6A . 109.5 C5 C6 H6B . 109.5 Cl1 C6 H6B . 109.5 H6A C6 H6B . 108.1 C5 N1 C1 . 117.82(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance C1 N1 . 1.3447(14) C1 C2 . 1.3958(15) C1 C1 3_667 1.489(2) C2 C3 . 1.3861(15) C2 H2 . 0.9500 C3 C4 . 1.3884(16) C3 H3 . 0.9500 C4 C5 . 1.3929(16) C4 H4 . 0.9500 C5 N1 . 1.3390(14) C5 C6 . 1.4989(15) C6 Cl1 . 1.8109(12) C6 H6A . 0.9900 C6 H6B . 0.9900 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 N1 C1 C2 C3 . -1.08(16) C1 C1 C2 C3 3_667 178.82(12) C1 C2 C3 C4 . -0.07(17) C2 C3 C4 C5 . 0.86(16) C3 C4 C5 N1 . -0.62(16) C3 C4 C5 C6 . 179.98(10) N1 C5 C6 Cl1 . 86.68(11) C4 C5 C6 Cl1 . -93.88(11) C4 C5 N1 C1 . -0.48(16) C6 C5 N1 C1 . 178.95(9) C2 C1 N1 C5 . 1.34(15) C1 C1 N1 C5 3_667 -178.57(11) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 1502060