#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/23/2202333.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_2202333 loop_ _publ_author_name 'Ramos Silva, Manuela' 'Matos Beja, Ana' 'Paix\~ao, Jose Antonio' _publ_section_title ; Pseudosymmetry in tetradecyltrimethylammonium bromide ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1151 _journal_page_last o1152 _journal_paper_doi 10.1107/S1600536803015319 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C17 H38 N 1+, Br 1-' _chemical_formula_moiety 'C17 H38 N 1+, Br 1-' _chemical_formula_sum 'C17 H38 Br N' _chemical_formula_weight 336.39 _chemical_name_systematic ; Tetradecyltrimethylammmonium bromide ; _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 SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.170(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.6323(13) _cell_length_b 7.240(2) _cell_length_c 47.3900(15) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.28 _cell_measurement_theta_min 22.97 _cell_volume 1932.1(7) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -58 _diffrn_reflns_number 6399 _diffrn_reflns_theta_full 72.55 _diffrn_reflns_theta_max 72.55 _diffrn_reflns_theta_min 3.73 _diffrn_standards_decay_% 10 _diffrn_standards_interval_time 180 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.800 _exptl_absorpt_correction_T_max 0.711 _exptl_absorpt_correction_T_min 0.471 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.966 _refine_diff_density_min -0.505 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 176 _refine_ls_number_reflns 3750 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0331 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.7670P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0893 _refine_ls_wR_factor_ref 0.1007 _reflns_number_gt 2481 _reflns_number_total 3750 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6302.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2202333 _cod_database_fobs_code 2202333 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 N1 0.4927(3) 0.7501(3) 0.54338(3) 0.0379(4) Uani d . 1 . . N C1 0.2998(3) 0.7528(3) 0.56497(4) 0.0422(5) Uani d . 1 . . C H1A 0.1857 0.6571 0.5601 0.051 Uiso calc R 1 . . H H1B 0.2178 0.8703 0.5635 0.051 Uiso calc R 1 . . H C1N 0.6390(4) 0.5784(3) 0.54550(5) 0.0489(6) Uani d . 1 . . C H1N1 0.7478 0.5746 0.5302 0.073 Uiso calc R 1 . . H H1N2 0.5368 0.4724 0.5446 0.073 Uiso calc R 1 . . H H1N3 0.7263 0.5780 0.5631 0.073 Uiso calc R 1 . . H C2 0.3766(4) 0.7254(3) 0.59536(4) 0.0515(6) Uani d . 1 . . C H2A 0.4216 0.5975 0.5985 0.062 Uiso calc R 1 . . H H2B 0.5134 0.8024 0.5997 0.062 Uiso calc R 1 . . H C2N 0.6509(4) 0.9152(3) 0.54615(5) 0.0505(6) Uani d . 1 . . C H2N1 0.7343 0.9112 0.5640 0.076 Uiso calc R 1 . . H H2N2 0.5568 1.0256 0.5450 0.076 Uiso calc R 1 . . H H2N3 0.7632 0.9147 0.5312 0.076 Uiso calc R 1 . . H C3 0.1750(4) 0.7758(4) 0.61436(5) 0.0573(7) Uani d . 1 . . C H3A 0.0323 0.7145 0.6074 0.069 Uiso calc R 1 . . H H3B 0.1481 0.9078 0.6129 0.069 Uiso calc R 1 . . H C3N 0.3697(4) 0.7551(4) 0.51505(4) 0.0527(6) Uani d . 1 . . C H3N1 0.4860 0.7555 0.5005 0.079 Uiso calc R 1 . . H H3N2 0.2745 0.8648 0.5136 0.079 Uiso calc R 1 . . H H3N3 0.2700 0.6483 0.5129 0.079 Uiso calc R 1 . . H C4 0.2116(4) 0.7268(4) 0.64525(4) 0.0553(7) Uani d . 1 . . C H4A 0.2197 0.5935 0.6471 0.066 Uiso calc R 1 . . H H4B 0.3627 0.7769 0.6518 0.066 Uiso calc R 1 . . H C5 0.0178(5) 0.7986(4) 0.66387(5) 0.0547(7) Uani d . 1 . . C H5A -0.1345 0.7626 0.6557 0.066 Uiso calc R 1 . . H H5B 0.0242 0.9325 0.6639 0.066 Uiso calc R 1 . . H C6 0.0312(5) 0.7313(4) 0.69410(4) 0.0546(6) Uani d . 1 . . C H6A 0.0217 0.5975 0.6941 0.066 Uiso calc R 1 . . H H6B 0.1845 0.7654 0.7022 0.066 Uiso calc R 1 . . H C7 -0.1609(5) 0.8068(4) 0.71254(5) 0.0551(7) Uani d . 1 . . C H7A -0.3140 0.7796 0.7038 0.066 Uiso calc R 1 . . H H7B -0.1450 0.9401 0.7135 0.066 Uiso calc R 1 . . H C8 -0.1575(4) 0.7304(4) 0.74246(5) 0.0533(6) Uani d . 1 . . C H8A -0.1766 0.5973 0.7416 0.064 Uiso calc R 1 . . H H8B -0.0035 0.7556 0.7512 0.064 Uiso calc R 1 . . H C9 -0.3481(5) 0.8094(4) 0.76097(5) 0.0545(6) Uani d . 1 . . C H9A -0.5020 0.7859 0.7521 0.065 Uiso calc R 1 . . H H9B -0.3274 0.9422 0.7621 0.065 Uiso calc R 1 . . H C10 -0.3468(5) 0.7308(4) 0.79062(5) 0.0551(6) Uani d . 1 . . C H10A -0.3688 0.5981 0.7894 0.066 Uiso calc R 1 . . H H10B -0.1923 0.7531 0.7994 0.066 Uiso calc R 1 . . H C11 -0.5350(5) 0.8100(4) 0.80937(5) 0.0571(7) Uani d . 1 . . C H11A -0.6897 0.7882 0.8006 0.068 Uiso calc R 1 . . H H11B -0.5126 0.9426 0.8107 0.068 Uiso calc R 1 . . H C12 -0.5327(5) 0.7293(4) 0.83902(5) 0.0582(7) Uani d . 1 . . C H12A -0.5570 0.5969 0.8377 0.070 Uiso calc R 1 . . H H12B -0.3773 0.7497 0.8477 0.070 Uiso calc R 1 . . H C13 -0.7195(6) 0.8103(4) 0.85805(5) 0.0695(8) Uani d . 1 . . C H13A -0.6939 0.9423 0.8597 0.083 Uiso calc R 1 . . H H13B -0.8751 0.7914 0.8494 0.083 Uiso calc R 1 . . H C14 -0.7163(8) 0.7261(5) 0.88719(6) 0.0968(13) Uani d . 1 . . C H14A -0.7473 0.5960 0.8858 0.145 Uiso calc R 1 . . H H14B -0.8363 0.7834 0.8983 0.145 Uiso calc R 1 . . H H14C -0.5633 0.7454 0.8960 0.145 Uiso calc R 1 . . H Br 0.11566(4) 0.25148(4) 0.539455(6) 0.05787(12) Uani d . 1 . . Br 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 N1 0.0351(8) 0.0420(10) 0.0367(7) -0.0001(9) 0.0044(6) -0.0015(9) C1 0.0342(9) 0.0552(13) 0.0374(9) 0.0033(11) 0.0061(7) -0.0003(12) C1N 0.0449(14) 0.0446(14) 0.0576(14) 0.0068(10) 0.0072(11) -0.0033(11) C2 0.0514(13) 0.0638(17) 0.0395(10) 0.0078(13) 0.0052(9) 0.0054(12) C2N 0.0461(14) 0.0479(14) 0.0577(14) -0.0082(11) 0.0066(12) 0.0011(11) C3 0.0567(14) 0.077(2) 0.0385(10) 0.0115(14) 0.0089(10) 0.0018(12) C3N 0.0520(12) 0.0717(16) 0.0345(9) 0.0019(13) 0.0003(8) -0.0029(12) C4 0.0544(13) 0.0714(19) 0.0403(10) 0.0049(13) 0.0096(9) 0.0038(12) C5 0.0585(14) 0.0676(18) 0.0385(10) 0.0060(13) 0.0097(10) 0.0016(11) C6 0.0572(14) 0.0652(18) 0.0418(10) 0.0047(13) 0.0098(10) 0.0021(12) C7 0.0598(14) 0.0652(18) 0.0408(11) 0.0020(13) 0.0088(10) -0.0001(11) C8 0.0561(13) 0.0624(17) 0.0419(10) 0.0002(13) 0.0100(10) 0.0002(12) C9 0.0596(15) 0.0604(16) 0.0438(11) 0.0018(13) 0.0098(10) -0.0011(11) C10 0.0583(14) 0.0626(18) 0.0448(11) 0.0009(13) 0.0114(10) 0.0017(12) C11 0.0611(16) 0.0637(16) 0.0468(12) 0.0007(13) 0.0101(11) -0.0020(11) C12 0.0689(16) 0.0603(18) 0.0458(11) -0.0030(14) 0.0132(11) 0.0017(12) C13 0.081(2) 0.075(2) 0.0529(14) -0.0059(16) 0.0223(14) -0.0063(14) C14 0.137(3) 0.101(3) 0.0544(15) -0.023(2) 0.0374(18) -0.0028(18) Br 0.04412(17) 0.04799(18) 0.08176(19) 0.00047(13) 0.00778(12) 0.00093(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 _geom_angle_publ_flag C1N N1 C2N 109.41(17) yes C1N N1 C3N 108.94(17) yes C2N N1 C3N 108.83(17) yes C1N N1 C1 111.68(17) yes C2N N1 C1 111.53(17) yes C3N N1 C1 106.35(15) yes N1 C1 C2 116.71(17) yes N1 C1 H1A 108.1 ? C2 C1 H1A 108.1 ? N1 C1 H1B 108.1 ? C2 C1 H1B 108.1 ? H1A C1 H1B 107.3 ? N1 C1N H1N1 109.5 ? N1 C1N H1N2 109.5 ? H1N1 C1N H1N2 109.5 ? N1 C1N H1N3 109.5 ? H1N1 C1N H1N3 109.5 ? H1N2 C1N H1N3 109.5 ? C3 C2 C1 109.47(19) ? C3 C2 H2A 109.8 ? C1 C2 H2A 109.8 ? C3 C2 H2B 109.8 ? C1 C2 H2B 109.8 ? H2A C2 H2B 108.2 ? N1 C2N H2N1 109.5 ? N1 C2N H2N2 109.5 ? H2N1 C2N H2N2 109.5 ? N1 C2N H2N3 109.5 ? H2N1 C2N H2N3 109.5 ? H2N2 C2N H2N3 109.5 ? C2 C3 C4 115.5(2) ? C2 C3 H3A 108.4 ? C4 C3 H3A 108.4 ? C2 C3 H3B 108.4 ? C4 C3 H3B 108.4 ? H3A C3 H3B 107.5 ? N1 C3N H3N1 109.5 ? N1 C3N H3N2 109.5 ? H3N1 C3N H3N2 109.5 ? N1 C3N H3N3 109.5 ? H3N1 C3N H3N3 109.5 ? H3N2 C3N H3N3 109.5 ? C5 C4 C3 113.5(2) ? C5 C4 H4A 108.9 ? C3 C4 H4A 108.9 ? C5 C4 H4B 108.9 ? C3 C4 H4B 108.9 ? H4A C4 H4B 107.7 ? C4 C5 C6 114.8(2) ? C4 C5 H5A 108.6 ? C6 C5 H5A 108.6 ? C4 C5 H5B 108.6 ? C6 C5 H5B 108.6 ? H5A C5 H5B 107.5 ? C7 C6 C5 114.2(2) ? C7 C6 H6A 108.7 ? C5 C6 H6A 108.7 ? C7 C6 H6B 108.7 ? C5 C6 H6B 108.7 ? H6A C6 H6B 107.6 ? C6 C7 C8 114.4(2) ? C6 C7 H7A 108.7 ? C8 C7 H7A 108.7 ? C6 C7 H7B 108.7 ? C8 C7 H7B 108.7 ? H7A C7 H7B 107.6 ? C9 C8 C7 114.0(2) ? C9 C8 H8A 108.7 ? C7 C8 H8A 108.7 ? C9 C8 H8B 108.7 ? C7 C8 H8B 108.7 ? H8A C8 H8B 107.6 ? C8 C9 C10 113.9(2) ? C8 C9 H9A 108.8 ? C10 C9 H9A 108.8 ? C8 C9 H9B 108.8 ? C10 C9 H9B 108.8 ? H9A C9 H9B 107.7 ? C11 C10 C9 114.4(2) ? 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 C12 113.9(2) ? C10 C11 H11A 108.8 ? C12 C11 H11A 108.8 ? C10 C11 H11B 108.8 ? C12 C11 H11B 108.8 ? H11A C11 H11B 107.7 ? C13 C12 C11 114.0(2) ? C13 C12 H12A 108.7 ? C11 C12 H12A 108.7 ? C13 C12 H12B 108.7 ? C11 C12 H12B 108.7 ? H12A C12 H12B 107.6 ? C14 C13 C12 113.1(3) ? C14 C13 H13A 109.0 ? C12 C13 H13A 109.0 ? C14 C13 H13B 109.0 ? C12 C13 H13B 109.0 ? H13A C13 H13B 107.8 ? C13 C14 H14A 109.5 ? C13 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? C13 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? 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 N1 C1N . 1.493(3) yes N1 C2N . 1.495(3) yes N1 C3N . 1.499(2) yes N1 C1 . 1.508(2) yes C1 C2 . 1.508(3) ? C1 H1A . 0.9700 ? C1 H1B . 0.9700 ? C1N H1N1 . 0.9600 ? C1N H1N2 . 0.9600 ? C1N H1N3 . 0.9600 ? C2 C3 . 1.508(3) ? C2 H2A . 0.9700 ? C2 H2B . 0.9700 ? C2N H2N1 . 0.9600 ? C2N H2N2 . 0.9600 ? C2N H2N3 . 0.9600 ? C3 C4 . 1.516(3) ? C3 H3A . 0.9700 ? C3 H3B . 0.9700 ? C3N H3N1 . 0.9600 ? C3N H3N2 . 0.9600 ? C3N H3N3 . 0.9600 ? C4 C5 . 1.510(3) ? C4 H4A . 0.9700 ? C4 H4B . 0.9700 ? C5 C6 . 1.513(3) ? C5 H5A . 0.9700 ? C5 H5B . 0.9700 ? C6 C7 . 1.507(3) ? C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? C7 C8 . 1.522(3) ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 C9 . 1.513(3) ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 C10 . 1.516(3) ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 C11 . 1.510(3) ? C10 H10A . 0.9700 ? C10 H10B . 0.9700 ? C11 C12 . 1.522(3) ? C11 H11A . 0.9700 ? C11 H11B . 0.9700 ? C12 C13 . 1.518(4) ? C12 H12A . 0.9700 ? C12 H12B . 0.9700 ? C13 C14 . 1.509(4) ? C13 H13A . 0.9700 ? C13 H13B . 0.9700 ? C14 H14A . 0.9600 ? C14 H14B . 0.9600 ? C14 H14C . 0.9600 ? 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 C1N N1 C1 C2 54.1(3) yes C2N N1 C1 C2 -68.7(2) yes C3N N1 C1 C2 172.8(2) yes N1 C1 C2 C3 166.8(2) yes C1 C2 C3 C4 170.7(2) ? C2 C3 C4 C5 173.6(2) ? C3 C4 C5 C6 172.3(2) ? C4 C5 C6 C7 179.0(2) ? C5 C6 C7 C8 176.4(2) ? C6 C7 C8 C9 179.0(2) ? C7 C8 C9 C10 179.1(2) ? C8 C9 C10 C11 179.5(2) ? C9 C10 C11 C12 179.7(2) ? C10 C11 C12 C13 179.3(3) ? C11 C12 C13 C14 179.1(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 13612 2 PubChem 14250