#------------------------------------------------------------------------------ #$Date$ #$Revision$ #$URL$ #------------------------------------------------------------------------------ # # 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_2016790 loop_ _publ_author_name 'Blerk, Charmaine van' 'Kruger, Gert J.' _publ_section_title ; Hydrogen-bonding motifs and thermotropic polymorphism in redetermined halide salts of hexamethylenediamine ; _journal_coeditor_code BM3056 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o537 _journal_page_last o542 _journal_volume 64 _journal_year 2008 _chemical_formula_iupac 'C6 H18 N2 2+ , 2Br -' _chemical_formula_moiety 'C6 H18 N2 2+ , 2(Br -)' _chemical_formula_sum 'C6 H18 Br2 N2' _chemical_formula_weight 278.04 _chemical_name_common 'Hexamethylenediammonium dihydrobromide' _chemical_name_systematic ; Hexane-1,6-diammonium dibromide ; _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 SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.1150(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.70440(10) _cell_length_b 14.4462(3) _cell_length_c 16.2582(4) _cell_measurement_reflns_used 9920 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 28.02 _cell_measurement_theta_min 2.51 _cell_volume 1104.92(4) _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_collection 'SMART-NT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_molecular_graphics ; X-SEED (Barbour, 2001) and Mercury (Macrae et al., 2006) ; _computing_publication_material ; PLATON (Spek, 2003) and publCIF (Westrip, 2008) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method '\f and \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 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 19693 _diffrn_reflns_theta_full 28.33 _diffrn_reflns_theta_max 28.33 _diffrn_reflns_theta_min 1.89 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 7.284 _exptl_absorpt_correction_T_max 0.4828 _exptl_absorpt_correction_T_min 0.1165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(APEX2 AXScale; Bruker, 2008)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rectangular _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.844 _refine_diff_density_min -0.649 _refine_ls_extinction_coef 0.0151(6) _refine_ls_extinction_expression Fc\^*\^=kFc[1+0.001xFc\^2\^\l\^3\^/sin(2\q)]\^-1/4\^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)' _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 94 _refine_ls_number_reflns 2753 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0253 _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^)+(0.0230P)^2^+0.7117P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.0599 _reflns_number_gt 2364 _reflns_number_total 2753 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm3056.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/c' 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_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_ _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 C C1 0.4145(5) 0.30294(17) 0.47953(15) 0.0406(5) Uani d . 1 H H1A 0.2816 0.2758 0.4408 0.049 Uiso calc R 1 H H1B 0.3058 0.3303 0.5239 0.049 Uiso calc R 1 C C2 0.6059(5) 0.22767(16) 0.51396(15) 0.0394(5) Uani d . 1 H H2A 0.7481 0.2557 0.5494 0.047 Uiso calc R 1 H H2B 0.7042 0.1974 0.4690 0.047 Uiso calc R 1 C C3 0.4408(5) 0.15551(17) 0.56270(16) 0.0428(5) Uani d . 1 H H3A 0.3418 0.1858 0.6076 0.051 Uiso calc R 1 H H3B 0.2994 0.1272 0.5272 0.051 Uiso calc R 1 C C4 0.6327(5) 0.08106(17) 0.59718(15) 0.0421(5) Uani d . 1 H H4A 0.7880 0.1104 0.6266 0.051 Uiso calc R 1 H H4B 0.7140 0.0465 0.5518 0.051 Uiso calc R 1 C C5 0.4852(5) 0.01335(17) 0.65505(16) 0.0431(5) Uani d . 1 H H5A 0.3924 0.0472 0.6990 0.052 Uiso calc R 1 H H5B 0.3413 -0.0211 0.6251 0.052 Uiso calc R 1 C C6 0.7001(5) -0.05245(19) 0.69073(16) 0.0476(6) Uani d . 1 H H6A 0.7850 -0.0876 0.6463 0.057 Uiso calc R 1 H H6B 0.8501 -0.0168 0.7168 0.057 Uiso calc R 1 N N1 0.5814(4) 0.37625(13) 0.43757(12) 0.0408(4) Uani d . 1 H H1C 0.6968 0.4034 0.4737 0.061 Uiso calc R 1 H H1D 0.4635 0.4182 0.4165 0.061 Uiso calc R 1 H H1E 0.6839 0.3511 0.3974 0.061 Uiso calc R 1 N N2 0.5816(4) -0.11829(14) 0.75204(12) 0.0411(4) Uani d . 1 H H2C 0.5006 -0.0868 0.7928 0.062 Uiso calc R 1 H H2D 0.7209 -0.1533 0.7722 0.062 Uiso calc R 1 H H2E 0.4523 -0.1542 0.7279 0.062 Uiso calc R 1 Br Br1 0.10941(5) -0.040380(16) 0.887786(14) 0.03875(9) Uani d . 1 Br Br2 0.92032(6) 0.226290(19) 0.784156(17) 0.05109(10) Uani d . 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 C1 0.0363(11) 0.0383(12) 0.0472(13) 0.0026(9) 0.0007(9) 0.0023(10) C2 0.0380(11) 0.0320(12) 0.0482(13) 0.0016(9) 0.0024(10) 0.0050(10) C3 0.0400(12) 0.0402(13) 0.0482(13) -0.0016(10) 0.0022(10) 0.0057(10) C4 0.0404(12) 0.0401(13) 0.0459(13) -0.0036(10) 0.0022(10) 0.0071(10) C5 0.0400(12) 0.0404(13) 0.0489(13) -0.0024(10) 0.0021(10) 0.0085(10) C6 0.0395(12) 0.0556(16) 0.0476(14) -0.0023(11) 0.0040(10) 0.0164(12) N1 0.0474(11) 0.0317(10) 0.0435(11) 0.0071(8) 0.0012(9) 0.0028(8) N2 0.0410(10) 0.0410(11) 0.0413(10) 0.0025(8) 0.0054(8) 0.0082(9) Br1 0.04040(13) 0.03815(14) 0.03770(13) -0.00208(9) 0.00054(9) -0.00454(9) Br2 0.05037(16) 0.04514(16) 0.05778(17) -0.00364(11) 0.00645(12) 0.01089(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.485(3) C1 C2 1.518(3) C1 H1A 0.9700 C1 H1B 0.9700 C2 C3 1.523(3) C2 H2A 0.9700 C2 H2B 0.9700 C3 C4 1.511(3) C3 H3A 0.9700 C3 H3B 0.9700 C4 C5 1.525(3) C4 H4A 0.9700 C4 H4B 0.9700 C5 C6 1.503(3) C5 H5A 0.9700 C5 H5B 0.9700 C6 N2 1.487(3) C6 H6A 0.9700 C6 H6B 0.9700 N1 H1C 0.8900 N1 H1D 0.8900 N1 H1E 0.8900 N2 H2C 0.8900 N2 H2D 0.8900 N2 H2E 0.8900 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 C2 111.50(19) N1 C1 H1A 109.3 C2 C1 H1A 109.3 N1 C1 H1B 109.3 C2 C1 H1B 109.3 H1A C1 H1B 108.0 C1 C2 C3 112.28(19) C1 C2 H2A 109.1 C3 C2 H2A 109.1 C1 C2 H2B 109.1 C3 C2 H2B 109.1 H2A C2 H2B 107.9 C4 C3 C2 112.0(2) C4 C3 H3A 109.2 C2 C3 H3A 109.2 C4 C3 H3B 109.2 C2 C3 H3B 109.2 H3A C3 H3B 107.9 C3 C4 C5 114.4(2) C3 C4 H4A 108.7 C5 C4 H4A 108.7 C3 C4 H4B 108.7 C5 C4 H4B 108.7 H4A C4 H4B 107.6 C6 C5 C4 109.7(2) C6 C5 H5A 109.7 C4 C5 H5A 109.7 C6 C5 H5B 109.7 C4 C5 H5B 109.7 H5A C5 H5B 108.2 N2 C6 C5 114.2(2) N2 C6 H6A 108.7 C5 C6 H6A 108.7 N2 C6 H6B 108.7 C5 C6 H6B 108.7 H6A C6 H6B 107.6 C1 N1 H1C 109.5 C1 N1 H1D 109.5 H1C N1 H1D 109.5 C1 N1 H1E 109.5 H1C N1 H1E 109.5 H1D N1 H1E 109.5 C6 N2 H2C 109.5 C6 N2 H2D 109.5 H2C N2 H2D 109.5 C6 N2 H2E 109.5 H2C N2 H2E 109.5 H2D N2 H2E 109.5 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 _geom_torsion_publ_flag N1 C1 C2 C3 175.8(2) yes C1 C2 C3 C4 -179.7(2) yes C2 C3 C4 C5 173.0(2) yes C3 C4 C5 C6 -175.4(2) yes C4 C5 C6 N2 176.6(2) yes 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 N1 H1C Br1 2_656 0.89 2.56 3.408(2) 159 N1 H1C Br1 4_665 0.89 3.11 3.529(2) 111 N1 H1D Br1 4_565 0.89 2.47 3.3466(19) 168 N1 H1E Br2 4_565 0.89 2.43 3.313(2) 174 N2 H2C Br1 . 0.89 2.50 3.330(2) 156 N2 H2D Br2 2_746 0.89 2.59 3.299(2) 137 N2 H2D Br1 1_655 0.89 3.09 3.505(2) 111 N2 H2E Br2 2_646 0.89 2.47 3.310(2) 158