#------------------------------------------------------------------------------ #$Date: 2016-03-24 03:18:35 +0200 (Thu, 24 Mar 2016) $ #$Revision: 179623 $ #$URL: svn://www.crystallography.net/cod/cif/4/50/87/4508718.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided the Crystal Eye server at # http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the # Peter Murray-Rust laboratory. # # 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_4508718 loop_ _publ_author_name 'Saha, Binoy K.' 'Nangia, Ashwini' 'Nicoud, Jean-Fran\,cois' _publ_section_title ; Using Halogen···Halogen Interactions to Direct Noncentrosymmetric Crystal Packing in Dipolar Organic Molecules ; _journal_issue 6 _journal_name_full 'Crystal Growth & Design' _journal_page_first 1278 _journal_paper_doi 10.1021/cg060117k _journal_volume 6 _journal_year 2006 _chemical_formula_moiety 'C5 H5 Br N2' _chemical_formula_sum 'C5 H5 Br N2' _chemical_formula_weight 173.02 _chemical_name_common 3-amino-2-bromopyridine _chemical_name_systematic ; 3-amino-2-bromopyridine ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 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 104.6860(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 7.9689(5) _cell_length_b 13.1908(8) _cell_length_c 11.6096(7) _cell_measurement_reflns_used 4857 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.23 _cell_measurement_theta_min 2.38 _cell_volume 1180.49(13) _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_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _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 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6730 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 1.81 _exptl_absorpt_coefficient_mu 6.845 _exptl_absorpt_correction_T_max 0.4267 _exptl_absorpt_correction_T_min 0.1705 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.947 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.494 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.083 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.278(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 321 _refine_ls_number_reflns 4274 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0243 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0307P)^2^+0.5804P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.0588 _reflns_number_gt 4146 _reflns_number_total 4274 _reflns_threshold_expression >2sigma(I) _cod_data_source_file cg060117ksup9.cif _cod_data_source_block an386_m _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 4508718 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 Br1 Br 0.33605(5) 0.67939(3) 1.16209(3) 0.02002(10) Uani 1 1 d . C4 C -0.0129(5) 0.4244(4) 0.9648(3) 0.0208(9) Uani 1 1 d . H4 H -0.0874 0.3709 0.9282 0.025 Uiso 1 1 calc R C5 C 0.0906(5) 0.4130(4) 1.0782(3) 0.0204(8) Uani 1 1 d . H5 H 0.0894 0.3502 1.1181 0.024 Uiso 1 1 calc R N2 N 0.1085(5) 0.6830(3) 0.9024(3) 0.0192(7) Uani 1 1 d . C1 C 0.1967(5) 0.5731(3) 1.0753(3) 0.0156(8) Uani 1 1 d . C2 C 0.1020(5) 0.5929(3) 0.9582(3) 0.0151(8) Uani 1 1 d . C3 C -0.0081(5) 0.5144(3) 0.9043(3) 0.0181(8) Uani 1 1 d . H3 H -0.0797 0.5228 0.8259 0.022 Uiso 1 1 calc R N1 N 0.1939(4) 0.4881(3) 1.1345(3) 0.0183(7) Uani 1 1 d . Br4 Br 0.29904(5) -0.08154(3) -0.19163(3) 0.01911(10) Uani 1 1 d . Br2 Br 0.36710(5) 0.89776(3) 0.35723(3) 0.02302(11) Uani 1 1 d . N4 N 0.5896(5) 0.9213(4) 0.6191(3) 0.0255(9) Uani 1 1 d . C6 C 0.6125(5) 0.9164(3) 0.4133(3) 0.0170(8) Uani 1 1 d . C7 C 0.6838(5) 0.9269(3) 0.5358(3) 0.0159(8) Uani 1 1 d . C9 C 0.9572(5) 0.9383(3) 0.4839(4) 0.0227(10) Uani 1 1 d . H9 H 1.0798 0.9456 0.5062 0.027 Uiso 1 1 calc R N3 N 0.6990(4) 0.9169(3) 0.3303(3) 0.0199(7) Uani 1 1 d . C8 C 0.8653(5) 0.9376(3) 0.5695(3) 0.0205(9) Uani 1 1 d . H8 H 0.9244 0.9444 0.6511 0.025 Uiso 1 1 calc R C10 C 0.8712(5) 0.9283(3) 0.3661(3) 0.0229(9) Uani 1 1 d . H10 H 0.9362 0.9295 0.3079 0.027 Uiso 1 1 calc R Br3 Br 1.25848(5) 0.71143(3) 0.59631(3) 0.02202(10) Uani 1 1 d . C13 C 0.7532(5) 0.6590(3) 0.4040(3) 0.0192(9) Uani 1 1 d . H13 H 0.6890 0.6498 0.3238 0.023 Uiso 1 1 calc R N5 N 0.9380(4) 0.6830(3) 0.6394(3) 0.0209(7) Uani 1 1 d . N6 N 1.0175(5) 0.6836(3) 0.3410(3) 0.0215(8) Uani 1 1 d . C12 C 0.9321(5) 0.6765(3) 0.4305(3) 0.0177(8) Uani 1 1 d . C11 C 1.0143(5) 0.6877(3) 0.5514(3) 0.0161(8) Uani 1 1 d . C14 C 0.6701(6) 0.6550(3) 0.4952(4) 0.0228(10) Uani 1 1 d . H14 H 0.5484 0.6442 0.4781 0.027 Uiso 1 1 calc R C15 C 0.7664(5) 0.6669(4) 0.6112(4) 0.0230(10) Uani 1 1 d . H15 H 0.7088 0.6634 0.6735 0.028 Uiso 1 1 calc R N8 N 0.5372(5) -0.0778(3) 0.0654(3) 0.0236(8) Uani 1 1 d . N7 N 0.2383(4) 0.1078(3) -0.1121(3) 0.0187(7) Uani 1 1 d . C17 C 0.4461(5) 0.0104(3) 0.0344(3) 0.0165(8) Uani 1 1 d . C16 C 0.3298(5) 0.0263(3) -0.0774(3) 0.0165(8) Uani 1 1 d . C18 C 0.4650(5) 0.0932(3) 0.1121(3) 0.0197(8) Uani 1 1 d . H18 H 0.5424 0.0891 0.1891 0.024 Uiso 1 1 calc R C19 C 0.3715(5) 0.1809(4) 0.0771(3) 0.0206(9) Uani 1 1 d . H19 H 0.3845 0.2373 0.1295 0.025 Uiso 1 1 calc R C20 C 0.2588(5) 0.1860(4) -0.0349(4) 0.0225(9) Uani 1 1 d . H20 H 0.1939 0.2463 -0.0582 0.027 Uiso 1 1 calc R H8A H 0.583(5) -0.085(3) 0.138(4) 0.003(9) Uiso 1 1 d . H6A H 1.125(7) 0.678(4) 0.358(4) 0.024(12) Uiso 1 1 d . H4B H 0.482(7) 0.928(4) 0.597(4) 0.033(14) Uiso 1 1 d . H6B H 0.962(6) 0.661(4) 0.282(4) 0.026(14) Uiso 1 1 d . H2A H 0.082(6) 0.690(4) 0.819(5) 0.038(14) Uiso 1 1 d . H2B H 0.187(7) 0.721(5) 0.923(4) 0.034(16) Uiso 1 1 d . H8B H 0.528(9) -0.122(5) 0.024(7) 0.07(2) Uiso 1 1 d . H4A H 0.646(6) 0.944(4) 0.697(4) 0.029(13) Uiso 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 Br1 0.01989(19) 0.0214(2) 0.01703(18) -0.00438(16) 0.00145(14) -0.00241(16) C4 0.0208(19) 0.020(2) 0.024(2) -0.0061(19) 0.0092(16) -0.0060(17) C5 0.024(2) 0.016(2) 0.0227(19) 0.0039(18) 0.0092(15) 0.0018(18) N2 0.0218(18) 0.0204(19) 0.0158(16) 0.0025(15) 0.0055(13) -0.0006(17) C1 0.0169(18) 0.017(2) 0.0144(17) -0.0020(15) 0.0061(15) 0.0015(15) C2 0.0170(18) 0.016(2) 0.0139(17) -0.0025(15) 0.0074(14) 0.0028(15) C3 0.0167(18) 0.023(2) 0.0149(17) -0.0055(16) 0.0042(14) 0.0023(16) N1 0.0206(17) 0.0182(18) 0.0169(16) 0.0022(14) 0.0060(13) 0.0031(14) Br4 0.02136(19) 0.0223(2) 0.01338(17) -0.00346(16) 0.00390(14) -0.00131(17) Br2 0.01962(19) 0.0278(3) 0.01879(19) -0.00449(17) -0.00044(14) -0.00006(17) N4 0.0190(18) 0.043(3) 0.0143(16) -0.0058(19) 0.0044(13) -0.0022(19) C6 0.0162(18) 0.015(2) 0.0181(18) 0.0004(17) 0.0019(14) 0.0008(17) C7 0.0200(18) 0.013(2) 0.0151(17) -0.0013(16) 0.0052(14) 0.0013(16) C9 0.019(2) 0.023(3) 0.027(2) 0.0009(18) 0.0063(17) -0.0011(18) N3 0.0248(17) 0.0178(18) 0.0171(15) 0.0008(16) 0.0053(13) 0.0037(16) C8 0.0212(19) 0.022(2) 0.0167(18) -0.0019(16) 0.0015(15) 0.0002(17) C10 0.032(2) 0.018(2) 0.023(2) 0.0064(18) 0.0153(18) 0.0045(19) Br3 0.02028(19) 0.0262(2) 0.01733(18) -0.00109(17) 0.00058(14) -0.00132(17) C13 0.021(2) 0.018(2) 0.0159(19) -0.0023(16) -0.0003(16) 0.0043(17) N5 0.0302(19) 0.0186(19) 0.0151(15) 0.0032(16) 0.0079(14) 0.0008(16) N6 0.0191(18) 0.031(2) 0.0134(16) -0.0002(17) 0.0026(14) 0.0005(17) C12 0.0239(19) 0.0141(19) 0.0142(17) 0.0038(16) 0.0031(14) 0.0043(17) C11 0.0169(17) 0.014(2) 0.0163(17) -0.0008(16) 0.0026(14) -0.0008(16) C14 0.024(2) 0.017(2) 0.028(2) 0.0000(18) 0.0090(17) 0.0018(17) C15 0.029(2) 0.020(2) 0.023(2) 0.0046(18) 0.0116(17) 0.0012(18) N8 0.0310(19) 0.024(2) 0.0130(18) -0.0008(17) 0.0007(14) 0.0012(18) N7 0.0190(17) 0.0224(19) 0.0164(16) -0.0005(14) 0.0077(13) -0.0010(14) C17 0.0165(18) 0.017(2) 0.0174(18) 0.0027(15) 0.0074(15) -0.0025(15) C16 0.0182(18) 0.018(2) 0.0153(18) -0.0011(16) 0.0079(15) -0.0022(16) C18 0.0196(19) 0.024(2) 0.0164(19) -0.0016(16) 0.0061(15) -0.0029(16) C19 0.029(2) 0.017(2) 0.0184(19) 0.0001(18) 0.0106(16) -0.0003(18) C20 0.021(2) 0.023(2) 0.024(2) 0.0005(19) 0.0085(16) -0.0009(19) 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' Br Br -0.2901 2.4595 '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 C5 C4 C3 119.5(4) C5 C4 H4 120.2 C3 C4 H4 120.2 N1 C5 C4 122.0(4) N1 C5 H5 119.0 C4 C5 H5 119.0 C2 N2 H2A 123(3) C2 N2 H2B 122(4) H2A N2 H2B 102(5) N1 C1 C2 126.0(4) N1 C1 Br1 115.7(3) C2 C1 Br1 118.2(3) N2 C2 C3 121.9(3) N2 C2 C1 123.2(4) C3 C2 C1 114.7(3) C4 C3 C2 120.2(3) C4 C3 H3 119.9 C2 C3 H3 119.9 C1 N1 C5 117.5(3) C7 N4 H4B 118(3) C7 N4 H4A 117(3) H4B N4 H4A 118(4) N3 C6 C7 126.1(3) N3 C6 Br2 115.5(3) C7 C6 Br2 118.4(3) N4 C7 C6 124.0(4) N4 C7 C8 121.3(3) C6 C7 C8 114.6(3) C10 C9 C8 119.8(4) C10 C9 H9 120.1 C8 C9 H9 120.1 C6 N3 C10 117.3(3) C9 C8 C7 119.9(4) C9 C8 H8 120.1 C7 C8 H8 120.1 N3 C10 C9 122.3(4) N3 C10 H10 118.9 C9 C10 H10 118.9 C14 C13 C12 119.7(4) C14 C13 H13 120.1 C12 C13 H13 120.1 C11 N5 C15 117.5(3) C12 N6 H6A 120(3) C12 N6 H6B 111(4) H6A N6 H6B 120(5) N6 C12 C11 123.6(4) N6 C12 C13 120.9(3) C11 C12 C13 115.5(3) N5 C11 C12 125.7(4) N5 C11 Br3 115.8(3) C12 C11 Br3 118.5(3) C15 C14 C13 119.1(4) C15 C14 H14 120.4 C13 C14 H14 120.4 N5 C15 C14 122.5(4) N5 C15 H15 118.7 C14 C15 H15 118.7 C17 N8 H8A 115(3) C17 N8 H8B 123(5) H8A N8 H8B 120(6) C16 N7 C20 117.4(3) N8 C17 C18 122.0(4) N8 C17 C16 123.4(4) C18 C17 C16 114.6(4) N7 C16 C17 126.5(4) N7 C16 Br4 115.8(3) C17 C16 Br4 117.8(3) C19 C18 C17 120.1(4) C19 C18 H18 119.9 C17 C18 H18 119.9 C18 C19 C20 119.5(4) C18 C19 H19 120.3 C20 C19 H19 120.3 N7 C20 C19 121.9(4) N7 C20 H20 119.1 C19 C20 H20 119.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C1 1.910(4) C4 C5 1.373(6) C4 C3 1.385(6) C4 H4 0.9500 C5 N1 1.347(5) C5 H5 0.9500 N2 C2 1.362(5) N2 H2A 0.95(5) N2 H2B 0.79(6) C1 N1 1.318(5) C1 C2 1.402(5) C2 C3 1.398(5) C3 H3 0.9500 Br4 C16 1.918(4) Br2 C6 1.914(4) N4 C7 1.368(5) N4 H4B 0.84(5) N4 H4A 0.95(5) C6 N3 1.318(5) C6 C7 1.399(5) C7 C8 1.407(5) C9 C10 1.371(6) C9 C8 1.376(6) C9 H9 0.9500 N3 C10 1.338(5) C8 H8 0.9500 C10 H10 0.9500 Br3 C11 1.908(4) C13 C14 1.385(6) C13 C12 1.400(6) C13 H13 0.9500 N5 C11 1.316(5) N5 C15 1.341(6) N6 C12 1.382(5) N6 H6A 0.83(5) N6 H6B 0.78(5) C12 C11 1.398(5) C14 C15 1.379(6) C14 H14 0.9500 C15 H15 0.9500 N8 C17 1.370(6) N8 H8A 0.83(4) N8 H8B 0.75(7) N7 C16 1.304(5) N7 C20 1.349(6) C17 C18 1.401(5) C17 C16 1.407(5) C18 C19 1.380(6) C18 H18 0.9500 C19 C20 1.382(6) C19 H19 0.9500 C20 H20 0.9500