#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202206.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_2202206 loop_ _publ_author_name 'Kruger, Gert J.' 'Rademeyer, Melanie' 'Billing, David G.' _publ_section_title ; n-Undecylammonium bromide monohydrate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o480 _journal_page_last o482 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C11 H26 N 1+ Br 1-, H2 O,' _chemical_formula_moiety 'C11 H26 N 1+ Br 1-, H2 O,' _chemical_formula_sum 'C11 H28 Br N O' _chemical_formula_weight 270.25 _chemical_name_systematic ; n-undecylammonium bromide monohydrate ; _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 90.00 _cell_angle_beta 105.65(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.809(6) _cell_length_b 40.353(5) _cell_length_c 7.882(9) _cell_measurement_reflns_used 1024 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22.376 _cell_measurement_theta_min 3.029 _cell_volume 1473(3) _computing_cell_refinement 'SAINT-Plus (Bruker, 1999)' _computing_data_collection 'SMART-NT (Bruker, 1998)' _computing_data_reduction 'XPREP (Bruker, 1999)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _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 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0843 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_k_min -53 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 10404 _diffrn_reflns_theta_full 28.31 _diffrn_reflns_theta_max 28.31 _diffrn_reflns_theta_min 1.01 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 2.769 _exptl_absorpt_correction_T_max 0.9215 _exptl_absorpt_correction_T_min 0.7505 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'thin plate' _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.355 _refine_diff_density_min -0.537 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 3647 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.943 _refine_ls_R_factor_all 0.1103 _refine_ls_R_factor_gt 0.0442 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0571P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0946 _refine_ls_wR_factor_ref 0.1234 _reflns_number_gt 1923 _reflns_number_total 3647 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file wn6139.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2202206 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Br 0.20924(9) 0.223762(11) 0.47014(6) 0.04986(17) Uani d . 1 . . Br N 0.6890(7) 0.21804(7) 0.8729(5) 0.0470(9) Uani d . 1 . . N H12A 0.8026 0.2357 0.8829 0.070 Uiso calc R 1 . . H H12B 0.6394 0.2151 0.9727 0.070 Uiso calc R 1 . . H H12C 0.5309 0.2211 0.7846 0.070 Uiso calc R 1 . . H C1 0.8460(8) 0.18836(9) 0.8368(5) 0.0438(10) Uani d . 1 . . C H1A 1.0201 0.1854 0.9321 0.053 Uiso calc R 1 . . H H1B 0.9029 0.1918 0.7290 0.053 Uiso calc R 1 . . H C2 0.6629(8) 0.15740(9) 0.8183(5) 0.0414(9) Uani d . 1 . . C H2A 0.4875 0.1605 0.7241 0.050 Uiso calc R 1 . . H H2B 0.6083 0.1537 0.9267 0.050 Uiso calc R 1 . . H C3 0.8226(9) 0.12716(9) 0.7788(5) 0.0462(10) Uani d . 1 . . C H3A 1.0121 0.1263 0.8622 0.055 Uiso calc R 1 . . H H3B 0.8497 0.1294 0.6618 0.055 Uiso calc R 1 . . H C4 0.6653(8) 0.09472(9) 0.7884(5) 0.0441(10) Uani d . 1 . . C H4A 0.6345 0.0928 0.9046 0.053 Uiso calc R 1 . . H H4B 0.4771 0.0955 0.7035 0.053 Uiso calc R 1 . . H C5 0.8231(9) 0.06420(10) 0.7529(5) 0.0465(10) Uani d . 1 . . C H5A 1.0147 0.0640 0.8341 0.056 Uiso calc R 1 . . H H5B 0.8455 0.0656 0.6345 0.056 Uiso calc R 1 . . H C6 0.6734(9) 0.03188(10) 0.7709(5) 0.0469(10) Uani d . 1 . . C H6A 0.4816 0.0322 0.6900 0.056 Uiso calc R 1 . . H H6B 0.6510 0.0305 0.8894 0.056 Uiso calc R 1 . . H C7 0.8284(9) 0.00102(9) 0.7356(5) 0.0456(10) Uani d . 1 . . C H7A 0.8505 0.0024 0.6171 0.055 Uiso calc R 1 . . H H7B 1.0204 0.0007 0.8164 0.055 Uiso calc R 1 . . H C8 0.6812(8) -0.03105(9) 0.7537(5) 0.0438(10) Uani d . 1 . . C H8A 0.4890 -0.0307 0.6732 0.053 Uiso calc R 1 . . H H8B 0.6597 -0.0324 0.8724 0.053 Uiso calc R 1 . . H C9 0.8355(9) -0.06181(10) 0.7179(5) 0.0473(10) Uani d . 1 . . C H9A 1.0277 -0.0621 0.7985 0.057 Uiso calc R 1 . . H H9B 0.8572 -0.0604 0.5993 0.057 Uiso calc R 1 . . H C10 0.6876(10) -0.09419(10) 0.7359(6) 0.0561(12) Uani d . 1 . . C H10A 0.6686 -0.0959 0.8550 0.067 Uiso calc R 1 . . H H10B 0.4945 -0.0939 0.6564 0.067 Uiso calc R 1 . . H C11 0.8425(11) -0.12445(11) 0.6973(7) 0.0733(14) Uani d . 1 . . C H11A 0.7362 -0.1439 0.7114 0.110 Uiso calc R 1 . . H H11B 1.0322 -0.1254 0.7774 0.110 Uiso calc R 1 . . H H11C 0.8578 -0.1234 0.5785 0.110 Uiso calc R 1 . . H O 0.5917(7) 0.19690(8) 0.1941(4) 0.0679(9) Uani d . 1 . . O H13A 0.7458 0.2036 0.2625 0.050 Uiso d . 1 . . H H13B 0.5024 0.2035 0.2621 0.050 Uiso d . 1 . . H 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 Br 0.0474(2) 0.0507(3) 0.0511(3) 0.0058(2) 0.01263(18) 0.0056(2) N 0.052(2) 0.033(2) 0.056(2) -0.0047(15) 0.0135(17) -0.0035(16) C1 0.046(2) 0.032(2) 0.054(2) 0.0043(18) 0.0152(19) 0.0056(19) C2 0.046(2) 0.031(2) 0.049(2) -0.0030(17) 0.0163(19) -0.0037(18) C3 0.056(3) 0.038(2) 0.048(2) -0.0003(19) 0.021(2) -0.0013(19) C4 0.048(2) 0.035(2) 0.051(2) 0.0010(18) 0.0159(19) -0.0029(19) C5 0.050(2) 0.040(2) 0.052(2) 0.0018(19) 0.019(2) -0.004(2) C6 0.052(2) 0.041(2) 0.051(2) 0.0020(19) 0.020(2) -0.002(2) C7 0.055(2) 0.036(2) 0.049(2) 0.0037(19) 0.020(2) 0.0002(19) C8 0.047(2) 0.040(2) 0.048(2) 0.0005(18) 0.0201(19) -0.0016(19) C9 0.052(2) 0.040(2) 0.051(2) 0.0045(19) 0.016(2) 0.000(2) C10 0.070(3) 0.039(3) 0.061(3) -0.004(2) 0.019(2) 0.000(2) C11 0.091(4) 0.042(3) 0.090(4) -0.003(3) 0.030(3) -0.009(3) O 0.072(2) 0.078(2) 0.0582(18) -0.0052(18) 0.0254(16) -0.0162(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N C1 . 1.484(5) ? N H12A . 0.8900 ? N H12B . 0.8900 ? N H12C . 0.8900 ? C1 C2 . 1.513(5) ? C1 H1A . 0.9700 ? C1 H1B . 0.9700 ? C2 C3 . 1.518(5) ? C2 H2A . 0.9700 ? C2 H2B . 0.9700 ? C3 C4 . 1.524(5) ? C3 H3A . 0.9700 ? C3 H3B . 0.9700 ? C4 C5 . 1.512(5) ? C4 H4A . 0.9700 ? C4 H4B . 0.9700 ? C5 C6 . 1.515(5) ? C5 H5A . 0.9700 ? C5 H5B . 0.9700 ? C6 C7 . 1.515(5) ? C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? C7 C8 . 1.500(5) ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 C9 . 1.511(5) ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 C10 . 1.513(6) ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 C11 . 1.504(6) ? C10 H10A . 0.9700 ? C10 H10B . 0.9700 ? C11 H11A . 0.9600 ? C11 H11B . 0.9600 ? C11 H11C . 0.9600 ? O H13A . 0.836 ? O H13B . 0.817 ? 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' Br Br -0.2901 2.4595 '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 C1 N H12A 109.5 C1 N H12B 109.5 H12A N H12B 109.5 C1 N H12C 109.5 H12A N H12C 109.5 H12B N H12C 109.5 N C1 C2 111.8(3) N C1 H1A 109.3 C2 C1 H1A 109.3 N C1 H1B 109.3 C2 C1 H1B 109.3 H1A C1 H1B 107.9 C1 C2 C3 111.7(3) C1 C2 H2A 109.3 C3 C2 H2A 109.3 C1 C2 H2B 109.3 C3 C2 H2B 109.3 H2A C2 H2B 107.9 C2 C3 C4 113.3(3) C2 C3 H3A 108.9 C4 C3 H3A 108.9 C2 C3 H3B 108.9 C4 C3 H3B 108.9 H3A C3 H3B 107.7 C5 C4 C3 114.2(3) C5 C4 H4A 108.7 C3 C4 H4A 108.7 C5 C4 H4B 108.7 C3 C4 H4B 108.7 H4A C4 H4B 107.6 C4 C5 C6 114.2(3) C4 C5 H5A 108.7 C6 C5 H5A 108.7 C4 C5 H5B 108.7 C6 C5 H5B 108.7 H5A C5 H5B 107.6 C5 C6 C7 114.9(3) C5 C6 H6A 108.5 C7 C6 H6A 108.5 C5 C6 H6B 108.5 C7 C6 H6B 108.5 H6A C6 H6B 107.5 C8 C7 C6 115.0(3) C8 C7 H7A 108.5 C6 C7 H7A 108.5 C8 C7 H7B 108.5 C6 C7 H7B 108.5 H7A C7 H7B 107.5 C7 C8 C9 115.0(3) C7 C8 H8A 108.5 C9 C8 H8A 108.5 C7 C8 H8B 108.5 C9 C8 H8B 108.5 H8A C8 H8B 107.5 C8 C9 C10 115.1(4) C8 C9 H9A 108.5 C10 C9 H9A 108.5 C8 C9 H9B 108.5 C10 C9 H9B 108.5 H9A C9 H9B 107.5 C11 C10 C9 114.3(4) C11 C10 H10A 108.7 C9 C10 H10A 108.7 C11 C10 H10B 108.7 C9 C10 H10B 108.7 H10A C10 H10B 107.6 C10 C11 H11A 109.5 C10 C11 H11B 109.5 H11A C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 H13A O H13B 90.1 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 _geom_hbond_publ_flag N H12A Br 4_666 0.89 2.50 3.366(4) 165 yes N H12B O 1_556 0.89 1.96 2.828(5) 164 yes N H12C Br . 0.89 2.55 3.392(5) 159 yes O H13A Br 1_655 0.84 2.517 3.353(4) 180 yes O H13B Br . 0.82 2.567 3.384(4) 179 yes 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 N C1 C2 C3 179.2(3) C1 C2 C3 C4 170.8(3) C2 C3 C4 C5 -178.9(3) C3 C4 C5 C6 177.2(3) C4 C5 C6 C7 179.9(3) C5 C6 C7 C8 179.9(3) C6 C7 C8 C9 179.8(3) C7 C8 C9 C10 -180.0(4) C8 C9 C10 C11 179.2(4) _cod_database_fobs_code 2202206 _journal_paper_doi 10.1107/S1600536803004859