#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/67/2016789.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_2016789 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+ , 2Cl -' _chemical_formula_moiety 'C6 H18 N2 2+ , 2(Cl -)' _chemical_formula_sum 'C6 H18 Cl2 N2' _chemical_formula_weight 189.12 _chemical_name_common 'Hexamethylenediammonium dihydrochloride' _chemical_name_systematic ; Hexane-1,6-diammonium dichloride ; _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 89.3270(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.60420(10) _cell_length_b 14.1570(3) _cell_length_c 15.6614(4) _cell_measurement_pressure 101.3 _cell_measurement_reflns_used 7105 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 2.60 _cell_volume 1020.77(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 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 0.021 _diffrn_reflns_av_sigmaI/netI 0.017 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 10699 _diffrn_reflns_theta_full 28.33 _diffrn_reflns_theta_max 28.33 _diffrn_reflns_theta_min 1.94 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.578 _exptl_absorpt_correction_T_max 0.9031 _exptl_absorpt_correction_T_min 0.7688 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(APEX2 AXScale; Bruker, 2008)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.37 _refine_diff_density_min -0.25 _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_constraints 0 _refine_ls_number_parameters 93 _refine_ls_number_reflns 2540 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.05 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0261 _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^)+(0.0381P)^2^+0.2526P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0720 _refine_ls_wR_factor_ref 0.0754 _reflns_number_gt 2195 _reflns_number_total 2540 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm3056.cif _[local]_cod_data_source_block I _[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' Cl Cl 0.1484 0.1585 '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 0.4217(2) 0.30716(8) 0.47640(8) 0.0348(2) Uani d . 1 H H1A 0.2900 0.2794 0.4355 0.042 Uiso calc R 1 H H1B 0.3058 0.3351 0.5220 0.042 Uiso calc R 1 C C2 0.6136(3) 0.23043(8) 0.51306(8) 0.0350(3) Uani d . 1 H H2A 0.7542 0.2591 0.5507 0.042 Uiso calc R 1 H H2B 0.7198 0.2000 0.4668 0.042 Uiso calc R 1 C C3 0.4414(3) 0.15602(8) 0.56252(8) 0.0363(3) Uani d . 1 H H3A 0.3344 0.1864 0.6087 0.044 Uiso calc R 1 H H3B 0.3019 0.1268 0.5248 0.044 Uiso calc R 1 C C4 0.6367(3) 0.08023(8) 0.59923(7) 0.0353(2) Uani d . 1 H H4A 0.7894 0.1106 0.6314 0.042 Uiso calc R 1 H H4B 0.7282 0.0461 0.5524 0.042 Uiso calc R 1 C C5 0.4812(3) 0.00937(9) 0.65728(8) 0.0363(3) Uani d . 1 H H5A 0.3806 0.0426 0.7030 0.044 Uiso calc R 1 H H5B 0.3385 -0.0255 0.6248 0.044 Uiso calc R 1 C C6 0.6998(3) -0.05814(9) 0.69430(8) 0.0399(3) Uani d . 1 H H6A 0.7939 -0.0922 0.6479 0.048 Uiso calc R 1 H H6B 0.8479 -0.0219 0.7233 0.048 Uiso calc R 1 N N1 0.5963(2) 0.38203(6) 0.43368(6) 0.0356(2) Uani d . 1 H H1C 0.7170 0.4077 0.4711 0.053 Uiso calc R 1 H H1D 0.4784 0.4264 0.4136 0.053 Uiso calc R 1 H H1E 0.6982 0.3569 0.3907 0.053 Uiso calc R 1 N N2 0.5737(2) -0.12784(7) 0.75545(6) 0.0385(2) Uani d . 1 H H2C 0.4937 -0.0974 0.7995 0.058 Uiso calc R 1 H H2D 0.7134 -0.1659 0.7740 0.058 Uiso calc R 1 H H2E 0.4387 -0.1619 0.7294 0.058 Uiso calc R 1 Cl Cl1 0.12529(6) -0.04025(2) 0.889257(17) 0.03620(10) Uani d . 1 Cl Cl2 0.92317(7) 0.22584(2) 0.78350(2) 0.04679(11) 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 0.0320(6) 0.0317(6) 0.0408(6) 0.0009(5) -0.0004(4) 0.0031(5) C2 0.0330(6) 0.0292(6) 0.0428(6) 0.0004(4) 0.0011(5) 0.0047(5) C3 0.0341(6) 0.0336(6) 0.0411(6) -0.0019(5) 0.0016(5) 0.0052(5) C4 0.0341(6) 0.0332(6) 0.0387(6) -0.0027(5) 0.0010(5) 0.0053(5) C5 0.0330(6) 0.0363(6) 0.0397(6) -0.0017(5) 0.0015(5) 0.0066(5) C6 0.0341(6) 0.0445(7) 0.0412(6) -0.0009(5) 0.0035(5) 0.0131(5) N1 0.0404(5) 0.0275(5) 0.0389(5) 0.0053(4) 0.0012(4) 0.0031(4) N2 0.0390(5) 0.0377(5) 0.0387(5) 0.0048(4) 0.0059(4) 0.0085(4) Cl1 0.03770(16) 0.03604(16) 0.03484(15) -0.00033(11) 0.00045(11) -0.00302(10) Cl2 0.04648(19) 0.04294(19) 0.05082(19) -0.00607(13) 0.00529(14) 0.00756(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.4849(14) C1 C2 1.5173(16) C1 H1A 0.9700 C1 H1B 0.9700 C2 C3 1.5244(15) C2 H2A 0.9700 C2 H2B 0.9700 C3 C4 1.5174(16) C3 H3A 0.9700 C3 H3B 0.9700 C4 C5 1.5265(15) C4 H4A 0.9700 C4 H4B 0.9700 C5 C6 1.5087(17) C5 H5A 0.9700 C5 H5B 0.9700 C6 N2 1.4880(14) 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 111.52(9) 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 112.67(10) C1 C2 H2A 109.1 C3 C2 H2A 109.1 C1 C2 H2B 109.1 C3 C2 H2B 109.1 H2A C2 H2B 107.8 C4 C3 C2 111.98(10) 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 114.48(10) C3 C4 H4A 108.6 C5 C4 H4A 108.6 C3 C4 H4B 108.6 C5 C4 H4B 108.6 H4A C4 H4B 107.6 C6 C5 C4 109.57(10) C6 C5 H5A 109.8 C4 C5 H5A 109.8 C6 C5 H5B 109.8 C4 C5 H5B 109.8 H5A C5 H5B 108.2 N2 C6 C5 114.24(10) 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 176.12(10) yes C1 C2 C3 C4 -179.62(10) yes C2 C3 C4 C5 173.90(10) yes C3 C4 C5 C6 -176.27(11) yes C4 C5 C6 N2 177.22(10) 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 Cl1 2_656 0.89 2.43 3.2599(11) 156 N1 H1C Cl1 4_665 0.89 2.94 3.3754(10) 112 N1 H1D Cl1 4_565 0.89 2.32 3.2000(10) 168 N1 H1E Cl2 4_565 0.89 2.29 3.1695(10) 172 N2 H2C Cl1 . 0.89 2.33 3.1765(10) 158 N2 H2D Cl2 2_746 0.89 2.43 3.1616(10) 139 N2 H2D Cl1 1_655 0.89 3.18 3.5361(11) 107 N2 H2E Cl2 2_646 0.89 2.31 3.1511(11) 157 _cod_database_code 2016789