#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2205021.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_2205021 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Zafra Stein' 'Israel Goldberg' _publ_section_title ; Tetra-n-butylammonium hexafluorophosphate at 110 K ; _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o272 _journal_page_last o274 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C16 H36 N +, P1 F6 -' _chemical_formula_moiety 'C16 H36 N +, F6 P -' _chemical_formula_sum 'C16 H36 F6 N P' _chemical_formula_weight 387.43 _chemical_name_systematic ; Tetra-n-butylammonium hexafluorophosphate ; _symmetry_cell_setting monoclinic _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 91.557(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.5559(2) _cell_length_b 13.8885(5) _cell_length_c 15.2346(5) _cell_measurement_reflns_used 4658 _cell_measurement_temperature 110(2) _cell_measurement_theta_max 28.17 _cell_measurement_theta_min 1.98 _cell_volume 2021.15(11) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_data_reduction DENZO _computing_molecular_graphics ; ORTEPIII (Burnett & Johnson, 1996) and MERCURY (Bruno et al., 2002) ; _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 110(2) _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w 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 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 17998 _diffrn_reflns_theta_full 28.17 _diffrn_reflns_theta_max 28.17 _diffrn_reflns_theta_min 1.98 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plates _exptl_crystal_F_000 832 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.475 _refine_diff_density_min -0.415 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 4839 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0483 _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^)+(0.0662P)^2^+0.7302P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1169 _refine_ls_wR_factor_ref 0.1301 _reflns_number_gt 3557 _reflns_number_total 4839 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cf6396.cif 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_type_symbol P 0.25562(4) 0.37706(3) 0.68699(3) 0.02163(13) Uani d . 1 P F1 0.15820(10) 0.45872(8) 0.72694(7) 0.0320(3) Uani d . 1 F F2 0.35254(11) 0.29484(9) 0.64747(9) 0.0418(3) Uani d . 1 F F3 0.38751(11) 0.42227(10) 0.73754(9) 0.0465(4) Uani d . 1 F F4 0.12340(12) 0.33452(11) 0.63415(10) 0.0554(4) Uani d . 1 F F5 0.22462(16) 0.31054(10) 0.76823(9) 0.0560(4) Uani d . 1 F F6 0.28664(16) 0.44466(11) 0.60473(9) 0.0582(4) Uani d . 1 F N 0.23196(13) 0.02821(10) 0.81107(9) 0.0180(3) Uani d . 1 N C1 0.10672(16) 0.09413(13) 0.82381(11) 0.0193(3) Uani d . 1 C H1A 0.0358 0.0807 0.7768 0.023 Uiso calc R 1 H H1B 0.1375 0.1617 0.8169 0.023 Uiso calc R 1 H C2 0.03783(16) 0.08385(13) 0.91243(11) 0.0208(4) Uani d . 1 C H2A 0.1096 0.0908 0.9601 0.025 Uiso calc R 1 H H2B -0.0042 0.0189 0.9170 0.025 Uiso calc R 1 H C3 -0.07588(17) 0.16032(13) 0.92315(12) 0.0250(4) Uani d . 1 C H3A -0.1390 0.1591 0.8705 0.030 Uiso calc R 1 H H3B -0.1322 0.1432 0.9745 0.030 Uiso calc R 1 H C4 -0.0206(2) 0.26185(15) 0.93557(14) 0.0346(5) Uani d . 1 C H4A 0.0467 0.2632 0.9852 0.052 Uiso calc R 1 H H4B -0.0985 0.3054 0.9473 0.052 Uiso calc R 1 H H4C 0.0257 0.2826 0.8822 0.052 Uiso calc R 1 H C5 0.34570(16) 0.04607(13) 0.88169(11) 0.0204(3) Uani d . 1 C H5A 0.3132 0.0202 0.9381 0.024 Uiso calc R 1 H H5B 0.4305 0.0096 0.8661 0.024 Uiso calc R 1 H C6 0.38576(16) 0.15124(13) 0.89478(11) 0.0222(4) Uani d . 1 C H6A 0.3088 0.1858 0.9235 0.027 Uiso calc R 1 H H6B 0.4007 0.1817 0.8370 0.027 Uiso calc R 1 H C7 0.51972(17) 0.15889(14) 0.95179(11) 0.0237(4) Uani d . 1 C H7A 0.5032 0.1305 1.0102 0.028 Uiso calc R 1 H H7B 0.5952 0.1217 0.9242 0.028 Uiso calc R 1 H C8 0.56606(18) 0.26315(15) 0.96303(13) 0.0303(4) Uani d . 1 C H8A 0.5809 0.2918 0.9052 0.045 Uiso calc R 1 H H8B 0.6536 0.2654 0.9980 0.045 Uiso calc R 1 H H8C 0.4935 0.2994 0.9931 0.045 Uiso calc R 1 H C9 0.18252(16) -0.07519(12) 0.81639(11) 0.0197(3) Uani d . 1 C H9A 0.1045 -0.0840 0.7731 0.024 Uiso calc R 1 H H9B 0.1444 -0.0857 0.8754 0.024 Uiso calc R 1 H C10 0.29141(17) -0.15264(13) 0.80034(12) 0.0229(4) Uani d . 1 C H10A 0.3707 -0.1455 0.8430 0.028 Uiso calc R 1 H H10B 0.3279 -0.1456 0.7405 0.028 Uiso calc R 1 H C11 0.22507(17) -0.25190(13) 0.81027(12) 0.0241(4) Uani d . 1 C H11A 0.1884 -0.2581 0.8702 0.029 Uiso calc R 1 H H11B 0.1451 -0.2580 0.7679 0.029 Uiso calc R 1 H C12 0.32892(19) -0.33310(14) 0.79462(12) 0.0288(4) Uani d . 1 C H12A 0.3638 -0.3283 0.7349 0.043 Uiso calc R 1 H H12B 0.2822 -0.3953 0.8019 0.043 Uiso calc R 1 H H12C 0.4076 -0.3279 0.8370 0.043 Uiso calc R 1 H C13 0.29434(16) 0.04962(13) 0.72206(11) 0.0206(4) Uani d . 1 C H13A 0.3855 0.0160 0.7193 0.025 Uiso calc R 1 H H13B 0.3135 0.1196 0.7190 0.025 Uiso calc R 1 H C14 0.20668(18) 0.02161(14) 0.64103(11) 0.0249(4) Uani d . 1 C H14A 0.1914 -0.0489 0.6401 0.030 Uiso calc R 1 H H14B 0.1143 0.0537 0.6422 0.030 Uiso calc R 1 H C15 0.2841(2) 0.05246(16) 0.55939(12) 0.0331(4) Uani d . 1 C H15A 0.2922 0.1235 0.5591 0.040 Uiso calc R 1 H H15B 0.3799 0.0255 0.5624 0.040 Uiso calc R 1 H C16 0.2120(2) 0.02004(16) 0.47401(13) 0.0391(5) Uani d . 1 C H16A 0.2118 -0.0505 0.4712 0.059 Uiso calc R 1 H H16B 0.2624 0.0460 0.4241 0.059 Uiso calc R 1 H H16C 0.1153 0.0437 0.4719 0.059 Uiso calc R 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 P 0.0167(2) 0.0211(3) 0.0272(2) 0.00022(17) 0.00293(16) 0.00046(18) F1 0.0221(5) 0.0326(7) 0.0412(6) 0.0076(4) 0.0007(4) -0.0075(5) F2 0.0314(6) 0.0336(7) 0.0608(8) 0.0075(5) 0.0117(5) -0.0121(6) F3 0.0188(5) 0.0521(9) 0.0683(9) 0.0006(5) -0.0056(5) -0.0224(7) F4 0.0280(6) 0.0655(10) 0.0722(10) -0.0011(6) -0.0081(6) -0.0370(8) F5 0.0724(9) 0.0420(8) 0.0548(8) 0.0077(7) 0.0255(7) 0.0247(7) F6 0.0795(10) 0.0536(9) 0.0429(8) 0.0100(8) 0.0236(7) 0.0183(7) N 0.0140(6) 0.0192(8) 0.0208(7) -0.0012(5) 0.0021(5) -0.0002(6) C1 0.0168(7) 0.0207(9) 0.0204(8) 0.0014(6) 0.0012(6) 0.0013(7) C2 0.0203(8) 0.0211(9) 0.0210(8) 0.0010(6) 0.0025(6) 0.0007(7) C3 0.0188(8) 0.0301(10) 0.0263(9) 0.0044(7) 0.0050(6) 0.0029(8) C4 0.0357(10) 0.0271(11) 0.0417(11) 0.0056(8) 0.0116(8) -0.0004(9) C5 0.0153(7) 0.0239(9) 0.0218(8) 0.0002(6) -0.0017(6) 0.0002(7) C6 0.0168(7) 0.0234(9) 0.0262(9) -0.0005(6) -0.0010(6) -0.0016(7) C7 0.0175(7) 0.0282(10) 0.0254(9) -0.0023(7) -0.0005(6) -0.0028(7) C8 0.0237(8) 0.0333(11) 0.0340(10) -0.0049(8) 0.0003(7) -0.0086(8) C9 0.0176(7) 0.0183(9) 0.0234(8) -0.0021(6) 0.0026(6) 0.0016(7) C10 0.0197(8) 0.0221(9) 0.0270(9) 0.0007(7) 0.0028(6) 0.0000(7) C11 0.0247(8) 0.0214(10) 0.0263(9) -0.0017(7) 0.0017(7) -0.0022(7) C12 0.0337(9) 0.0226(10) 0.0301(10) 0.0020(8) 0.0024(7) -0.0026(8) C13 0.0187(7) 0.0223(9) 0.0209(8) -0.0018(6) 0.0044(6) 0.0011(7) C14 0.0256(8) 0.0276(10) 0.0214(8) -0.0043(7) 0.0016(7) 0.0003(7) C15 0.0378(10) 0.0385(12) 0.0231(9) -0.0066(9) 0.0061(8) 0.0014(8) C16 0.0598(13) 0.0340(12) 0.0236(10) -0.0023(10) 0.0046(9) 0.0004(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag P F5 1.5791(13) yes P F3 1.5884(12) yes P F4 1.5933(12) yes P F2 1.5985(11) yes P F1 1.5981(11) yes P F6 1.6000(13) yes N C9 1.515(2) yes N C1 1.524(2) yes N C13 1.525(2) yes N C5 1.529(2) yes C1 C2 1.525(2) ? C1 H1A 0.990 ? C1 H1B 0.990 ? C2 C3 1.531(2) ? C2 H2A 0.990 ? C2 H2B 0.990 ? C3 C4 1.516(3) ? C3 H3A 0.990 ? C3 H3B 0.990 ? C4 H4A 0.980 ? C4 H4B 0.980 ? C4 H4C 0.980 ? C5 C6 1.522(2) ? C5 H5A 0.990 ? C5 H5B 0.990 ? C6 C7 1.531(2) ? C6 H6A 0.990 ? C6 H6B 0.990 ? C7 C8 1.523(3) ? C7 H7A 0.990 ? C7 H7B 0.990 ? C8 H8A 0.980 ? C8 H8B 0.980 ? C8 H8C 0.980 ? C9 C10 1.521(2) ? C9 H9A 0.990 ? C9 H9B 0.990 ? C10 C11 1.527(2) ? C10 H10A 0.990 ? C10 H10B 0.990 ? C11 C12 1.525(2) ? C11 H11A 0.990 ? C11 H11B 0.990 ? C12 H12A 0.980 ? C12 H12B 0.980 ? C12 H12C 0.980 ? C13 C14 1.523(2) ? C13 H13A 0.990 ? C13 H13B 0.990 ? C14 C15 1.526(2) ? C14 H14A 0.990 ? C14 H14B 0.990 ? C15 C16 1.523(3) ? C15 H15A 0.990 ? C15 H15B 0.990 ? C16 H16A 0.980 ? C16 H16B 0.980 ? C16 H16C 0.980 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle F5 P F3 90.84(9) F5 P F4 90.91(9) F3 P F4 178.17(9) F5 P F2 90.01(7) F3 P F2 90.27(7) F4 P F2 90.25(7) F5 P F1 89.60(7) F3 P F1 89.87(6) F4 P F1 89.62(6) F2 P F1 179.59(7) F5 P F6 179.83(9) F3 P F6 89.22(8) F4 P F6 89.03(9) F2 P F6 90.15(7) F1 P F6 90.24(7) C9 N C1 108.40(12) C9 N C13 111.25(13) C1 N C13 108.87(12) C9 N C5 109.45(12) C1 N C5 111.03(12) C13 N C5 107.85(11) N C1 C2 114.59(13) N C1 H1A 108.6 C2 C1 H1A 108.6 N C1 H1B 108.6 C2 C1 H1B 108.6 H1A C1 H1B 107.6 C1 C2 C3 110.74(14) C1 C2 H2A 109.5 C3 C2 H2A 109.5 C1 C2 H2B 109.5 C3 C2 H2B 109.5 H2A C2 H2B 108.1 C4 C3 C2 114.37(14) C4 C3 H3A 108.7 C2 C3 H3A 108.7 C4 C3 H3B 108.7 C2 C3 H3B 108.7 H3A C3 H3B 107.6 C3 C4 H4A 109.5 C3 C4 H4B 109.5 H4A C4 H4B 109.5 C3 C4 H4C 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 C6 C5 N 114.80(13) C6 C5 H5A 108.6 N C5 H5A 108.6 C6 C5 H5B 108.6 N C5 H5B 108.6 H5A C5 H5B 107.5 C5 C6 C7 110.14(14) C5 C6 H6A 109.6 C7 C6 H6A 109.6 C5 C6 H6B 109.6 C7 C6 H6B 109.6 H6A C6 H6B 108.1 C8 C7 C6 111.47(15) C8 C7 H7A 109.3 C6 C7 H7A 109.3 C8 C7 H7B 109.3 C6 C7 H7B 109.3 H7A C7 H7B 108.0 C7 C8 H8A 109.5 C7 C8 H8B 109.5 H8A C8 H8B 109.5 C7 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 N C9 C10 116.50(13) N C9 H9A 108.2 C10 C9 H9A 108.2 N C9 H9B 108.2 C10 C9 H9B 108.2 H9A C9 H9B 107.3 C9 C10 C11 109.57(13) C9 C10 H10A 109.8 C11 C10 H10A 109.8 C9 C10 H10B 109.8 C11 C10 H10B 109.8 H10A C10 H10B 108.2 C12 C11 C10 112.25(14) C12 C11 H11A 109.2 C10 C11 H11A 109.2 C12 C11 H11B 109.2 C10 C11 H11B 109.2 H11A C11 H11B 107.9 C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 N C13 C14 116.81(13) N C13 H13A 108.1 C14 C13 H13A 108.1 N C13 H13B 108.1 C14 C13 H13B 108.1 H13A C13 H13B 107.3 C15 C14 C13 108.72(14) C15 C14 H14A 109.9 C13 C14 H14A 109.9 C15 C14 H14B 109.9 C13 C14 H14B 109.9 H14A C14 H14B 108.3 C16 C15 C14 113.28(16) C16 C15 H15A 108.9 C14 C15 H15A 108.9 C16 C15 H15B 108.9 C14 C15 H15B 108.9 H15A C15 H15B 107.7 C15 C16 H16A 109.5 C15 C16 H16B 109.5 H16A C16 H16B 109.5 C15 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 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 C9 N C1 C2 61.60(17) ? C13 N C1 C2 -177.24(14) ? C5 N C1 C2 -58.66(18) ? N C1 C2 C3 173.68(13) yes C1 C2 C3 C4 -70.8(2) yes C9 N C5 C6 -169.30(13) ? C1 N C5 C6 -49.67(17) ? C13 N C5 C6 69.53(17) ? N C5 C6 C7 -168.00(13) yes C5 C6 C7 C8 177.64(14) yes C1 N C9 C10 176.84(14) ? C13 N C9 C10 57.16(18) ? C5 N C9 C10 -61.92(18) ? N C9 C10 C11 178.68(13) yes C9 C10 C11 C12 179.79(15) yes C9 N C13 C14 50.62(19) ? C1 N C13 C14 -68.78(18) ? C5 N C13 C14 170.66(15) ? N C13 C14 C15 177.72(15) yes C13 C14 C15 C16 174.88(17) yes