#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202299.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_2202299 loop_ _publ_author_name 'Harrison, William T. A.' _publ_section_title ; 4-Aza-1-azoniabicyclo[2.2.2]octane dihydrogenphosphite ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1351 _journal_page_last o1353 _journal_paper_doi 10.1107/S1600536803018130 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C6 H13 N2 1+, H2 O3 P 1-' _chemical_formula_moiety 'C6 H13 N2 1+, H2 O3 P 1-' _chemical_formula_sum 'C6 H15 N2 O3 P' _chemical_formula_weight 194.17 _chemical_name_common 'dabconium phosphite' _chemical_name_systematic ; 4-Aza-1-azoniabicyclo[2.2.2]octane dihydrogenphosphite ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens 'difmap (O-H, N-H) and geom (C-H, P-H)' _atom_sites_solution_primary direct _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.6418(4) _cell_length_b 9.9428(6) _cell_length_c 14.0575(8) _cell_measurement_reflns_used 3200 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.27 _cell_measurement_theta_min 2.51 _cell_volume 928.33(10) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and ATOMS (Shape Software, 1999)' _computing_publication_material SHELXL97 _computing_structure_refinement SHELXL97 _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART1000 CCD' _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 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 6962 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.51 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_correction_T_min 0.886 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1999)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 416 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.231 _refine_diff_density_min -0.261 _refine_ls_abs_structure_details 'Flack (1983), 881 Friedel pairs' _refine_ls_abs_structure_Flack 0.15(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 110 _refine_ls_number_reflns 2139 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0366 _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^)+(0.0606P)^2^+0.0257P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0942 _refine_ls_wR_factor_ref 0.0979 _reflns_number_gt 1861 _reflns_number_total 2139 _reflns_threshold_expression I>2\s(I) _cod_data_source_file br6113.cif _cod_data_source_block I _cod_database_code 2202299 _cod_database_fobs_code 2202299 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 P1 0.72109(8) 0.62955(5) 0.58804(4) 0.04115(15) Uani d . 1 . . P H1 0.6694 0.5401 0.5231 0.049 Uiso calc R 1 . . H O1 0.9539(2) 0.64524(19) 0.58243(12) 0.0655(5) Uani d . 1 . . O H2 1.0090 0.6853 0.5241 0.079 Uiso d R 1 . . H O2 0.6770(3) 0.5684(2) 0.68263(12) 0.0697(6) Uani d . 1 . . O O3 0.6123(3) 0.75504(19) 0.56514(13) 0.0698(5) Uani d . 1 . . O N1 0.3717(3) 0.61178(18) 0.79192(12) 0.0432(4) Uani d . 1 . . N H3 0.4784 0.6026 0.7518 0.052 Uiso calc R 1 . . H N2 0.0775(3) 0.63634(19) 0.90403(15) 0.0540(4) Uani d . 1 . . N C1 0.2246(4) 0.5024(2) 0.77401(16) 0.0515(5) Uani d . 1 . . C H4 0.2900 0.4156 0.7800 0.062 Uiso calc R 1 . . H H5 0.1708 0.5101 0.7101 0.062 Uiso calc R 1 . . H C2 0.0544(4) 0.5145(2) 0.84689(19) 0.0597(6) Uani d . 1 . . C H6 -0.0740 0.5168 0.8141 0.072 Uiso calc R 1 . . H H7 0.0555 0.4364 0.8882 0.072 Uiso calc R 1 . . H C3 0.4417(4) 0.6009(3) 0.89150(17) 0.0682(8) Uani d . 1 . . C H8 0.5471 0.6663 0.9035 0.082 Uiso calc R 1 . . H H9 0.4959 0.5118 0.9031 0.082 Uiso calc R 1 . . H C4 0.2638(5) 0.6269(4) 0.95691(18) 0.0770(8) Uani d . 1 . . C H10 0.2537 0.5544 1.0029 0.092 Uiso calc R 1 . . H H11 0.2858 0.7100 0.9915 0.092 Uiso calc R 1 . . H C5 0.2721(5) 0.7432(2) 0.7746(2) 0.0652(7) Uani d . 1 . . C H12 0.2341 0.7510 0.7082 0.078 Uiso calc R 1 . . H H13 0.3634 0.8162 0.7899 0.078 Uiso calc R 1 . . H C6 0.0845(4) 0.7503(2) 0.8380(2) 0.0652(7) Uani d . 1 . . C H14 0.0860 0.8337 0.8738 0.078 Uiso calc R 1 . . H H15 -0.0352 0.7498 0.7985 0.078 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 P1 0.0450(3) 0.0391(2) 0.0394(2) 0.0019(2) -0.0010(2) 0.0008(2) O1 0.0491(9) 0.0900(13) 0.0575(9) 0.0011(9) 0.0012(8) 0.0288(11) O2 0.0639(12) 0.0796(12) 0.0657(11) 0.0160(10) 0.0243(9) 0.0282(10) O3 0.0758(13) 0.0634(10) 0.0702(12) 0.0191(9) -0.0149(9) 0.0115(9) N1 0.0410(8) 0.0435(9) 0.0450(8) 0.0003(7) 0.0036(7) 0.0014(8) N2 0.0542(10) 0.0473(10) 0.0607(10) 0.0074(9) 0.0144(9) 0.0016(11) C1 0.0593(14) 0.0393(10) 0.0558(12) -0.0046(10) 0.0007(11) -0.0043(9) C2 0.0515(14) 0.0450(12) 0.0825(17) -0.0061(10) 0.0080(13) 0.0028(12) C3 0.0520(14) 0.097(2) 0.0553(13) -0.0019(13) -0.0110(10) -0.0049(14) C4 0.0820(19) 0.103(2) 0.0457(12) 0.0073(19) -0.0005(13) -0.0099(15) C5 0.0828(19) 0.0349(10) 0.0778(16) 0.0053(12) 0.0222(15) 0.0121(11) C6 0.0681(16) 0.0369(12) 0.0908(19) 0.0101(11) 0.0117(15) 0.0019(13) 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' O O 0.0106 0.0060 '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' 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 O3 P1 O2 116.25(11) yes O3 P1 O1 112.98(12) yes O2 P1 O1 106.34(10) yes O3 P1 H1 106.9 ? O2 P1 H1 106.9 ? O1 P1 H1 106.9 ? P1 O1 H2 117.0 ? C3 N1 C1 108.32(19) ? C3 N1 C5 111.1(2) ? C1 N1 C5 108.90(19) ? C3 N1 H3 109.5 ? C1 N1 H3 109.5 ? C5 N1 H3 109.5 ? C4 N2 C2 108.5(2) ? C4 N2 C6 110.4(2) ? C2 N2 C6 107.24(19) ? N1 C1 C2 108.39(17) ? N1 C1 H4 110.0 ? C2 C1 H4 110.0 ? N1 C1 H5 110.0 ? C2 C1 H5 110.0 ? H4 C1 H5 108.4 ? N2 C2 C1 110.81(19) ? N2 C2 H6 109.5 ? C1 C2 H6 109.5 ? N2 C2 H7 109.5 ? C1 C2 H7 109.5 ? H6 C2 H7 108.1 ? N1 C3 C4 108.4(2) ? N1 C3 H8 110.0 ? C4 C3 H8 110.0 ? N1 C3 H9 110.0 ? C4 C3 H9 110.0 ? H8 C3 H9 108.4 ? N2 C4 C3 111.43(19) ? N2 C4 H10 109.3 ? C3 C4 H10 109.3 ? N2 C4 H11 109.3 ? C3 C4 H11 109.3 ? H10 C4 H11 108.0 ? N1 C5 C6 107.86(18) ? N1 C5 H12 110.1 ? C6 C5 H12 110.1 ? N1 C5 H13 110.1 ? C6 C5 H13 110.1 ? H12 C5 H13 108.4 ? N2 C6 C5 111.02(19) ? N2 C6 H14 109.4 ? C5 C6 H14 109.4 ? N2 C6 H15 109.4 ? C5 C6 H15 109.4 ? H14 C6 H15 108.0 ? 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 P1 O3 . 1.4774(19) yes P1 O2 . 1.4910(16) yes P1 O1 . 1.5561(18) yes P1 H1 . 1.3200 ? O1 H2 . 0.9825 ? N1 C3 . 1.479(3) ? N1 C1 . 1.483(3) ? N1 C5 . 1.485(3) ? N1 H3 . 0.9100 ? N2 C4 . 1.447(4) ? N2 C2 . 1.462(3) ? N2 C6 . 1.465(3) ? C1 C2 . 1.530(3) ? C1 H4 . 0.9700 ? C1 H5 . 0.9700 ? C2 H6 . 0.9700 ? C2 H7 . 0.9700 ? C3 C4 . 1.519(4) ? C3 H8 . 0.9700 ? C3 H9 . 0.9700 ? C4 H10 . 0.9700 ? C4 H11 . 0.9700 ? C5 C6 . 1.534(4) ? C5 H12 . 0.9700 ? C5 H13 . 0.9700 ? C6 H14 . 0.9700 ? C6 H15 . 0.9700 ? 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 O1 H2 O3 4_566 0.98 1.55 2.528(2) 176 yes N1 H3 O2 . 0.91 1.67 2.580(2) 174 yes