#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/75/2217576.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_2217576 loop_ _publ_author_name 'Kirillov, Alexander M.' 'Smole\'nski, Piotr' 'Guedes da Silva, M. F\'atima C.' 'Pombeiro, Armando J. L.' _publ_section_title ; 1-Methyl-1-azonia-3,5-diaza-7-phosphatricyclo[3.3.1.1]decane 7-oxide triiodide ; _journal_coeditor_code KP2159 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o496 _journal_page_last o497 _journal_volume 64 _journal_year 2008 _chemical_formula_iupac 'C7 H15 N3 O P + , I3 -' _chemical_formula_moiety 'C7 H15 N3 O P + , I3 -' _chemical_formula_sum 'C7 H15 Cu0 I3 N3 O P' _chemical_formula_weight 568.89 _chemical_name_systematic ; 1-Methyl-1-azonia-3,5-diaza-7-phosphatricyclo[3.3.1.1]decane 7-oxide triiodide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 92.472(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.1570(8) _cell_length_b 8.2257(8) _cell_length_c 25.903(3) _cell_measurement_reflns_used 2835 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.93 _cell_measurement_theta_min 2.6 _cell_volume 1523.5(3) _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_collection 'SMART (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_molecular_graphics 'Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'WinGX (Version 1.70.01; Farrugia, 1999)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 11526 _diffrn_reflns_theta_full 25.35 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_min 2.92 _exptl_absorpt_coefficient_mu 6.244 _exptl_absorpt_correction_T_max 0.5740 _exptl_absorpt_correction_T_min 0.4974 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 2.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1040 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 2.441 _refine_diff_density_min -1.033 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 172 _refine_ls_number_reflns 2789 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.122 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0415 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0450P)^2^+6.2243P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0978 _refine_ls_wR_factor_ref 0.1023 _reflns_number_gt 2214 _reflns_number_total 2789 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file kp2159.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P21/n _[local]_cod_cif_authors_sg_Hall -P2yn _cod_database_code 2217576 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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' 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 0.5522(9) 0.4541(10) 0.1979(3) 0.0186(16) Uani d . 1 C C2 0.5510(9) 0.1132(8) 0.1974(3) 0.0156(15) Uani d . 1 C C3 0.5535(10) 0.2823(10) 0.1042(3) 0.0188(15) Uani d . 1 C C4 0.8586(11) 0.2823(11) 0.0631(3) 0.0294(18) Uani d . 1 H H4A 0.9942 0.2819 0.0701 0.044 Uiso calc R 1 H H4B 0.8230 0.3796 0.0432 0.044 Uiso calc R 1 H H4C 0.8222 0.1851 0.0432 0.044 Uiso calc R 1 C C12 0.8197(10) 0.2815(10) 0.2227(3) 0.0192(15) Uani d . 1 C C23 0.8255(10) 0.1301(8) 0.1442(3) 0.0162(15) Uani d . 1 C C31 0.8255(10) 0.4347(10) 0.1446(3) 0.0192(16) Uani d . 1 N N1 0.7565(7) 0.4292(7) 0.1960(2) 0.0169(13) Uani d . 1 N N2 0.7569(7) 0.1334(7) 0.1956(2) 0.0141(12) Uani d . 1 N N3 0.7614(8) 0.2828(7) 0.1131(2) 0.0168(12) Uani d . 1 O O1 0.2300(7) 0.2825(7) 0.1582(2) 0.0268(12) Uani d . 1 P P1 0.4367(2) 0.2827(2) 0.16547(7) 0.0168(4) Uani d . 1 I I1 0.42016(7) 0.78153(6) 0.088953(18) 0.02270(15) Uani d . 1 I I2 0.14227(7) 0.78170(6) 0.16786(2) 0.02691(16) Uani d . 1 I I3 0.73414(8) 0.78543(8) 0.02143(2) 0.03606(18) Uani d . 1 H H1A 0.517(12) 0.452(11) 0.232(4) 0.043 Uiso d . 1 H H1B 0.498(12) 0.558(11) 0.183(3) 0.043 Uiso d . 1 H H2A 0.501(12) 0.108(11) 0.232(4) 0.043 Uiso d . 1 H H2B 0.521(12) 0.008(12) 0.182(3) 0.050 Uiso d . 1 H H3A 0.512(14) 0.190(12) 0.084(4) 0.060 Uiso d . 1 H H3B 0.522(14) 0.380(13) 0.085(4) 0.060 Uiso d . 1 H H12A 0.948(16) 0.286(12) 0.225(4) 0.060 Uiso d . 1 H H12B 0.793(14) 0.282(11) 0.256(4) 0.050 Uiso d . 1 H H23A 0.964(15) 0.135(13) 0.147(4) 0.060 Uiso d . 1 H H23B 0.769(13) 0.034(13) 0.127(4) 0.060 Uiso d . 1 H H31A 0.959(14) 0.414(12) 0.147(4) 0.060 Uiso d . 1 H H31B 0.768(13) 0.538(13) 0.126(4) 0.060 Uiso 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 0.010(3) 0.026(5) 0.020(4) 0.005(3) 0.001(3) -0.003(3) C2 0.014(3) 0.011(4) 0.022(4) -0.002(3) 0.006(3) 0.000(3) C3 0.013(3) 0.021(4) 0.023(4) 0.002(3) -0.003(3) 0.000(3) C4 0.027(4) 0.041(5) 0.022(4) -0.001(4) 0.017(3) -0.007(4) C12 0.016(4) 0.021(4) 0.020(4) -0.001(3) -0.006(3) 0.000(3) C23 0.018(4) 0.006(4) 0.026(4) 0.004(3) 0.005(3) 0.002(3) C31 0.012(4) 0.027(5) 0.019(4) 0.001(3) 0.002(3) 0.001(3) N1 0.011(3) 0.020(3) 0.019(3) -0.001(2) -0.002(2) 0.000(3) N2 0.009(3) 0.017(3) 0.017(3) 0.001(2) 0.002(2) 0.002(2) N3 0.014(3) 0.020(3) 0.016(3) -0.005(3) 0.002(2) -0.004(3) O1 0.009(2) 0.029(3) 0.042(3) 0.000(2) -0.002(2) 0.002(3) P1 0.0075(8) 0.0187(9) 0.0244(10) 0.0007(7) 0.0003(7) -0.0004(8) I1 0.0282(3) 0.0183(3) 0.0215(3) 0.0009(2) -0.00114(19) -0.0002(2) I2 0.0230(3) 0.0207(3) 0.0376(3) 0.0000(2) 0.0081(2) 0.0000(2) I3 0.0341(3) 0.0527(4) 0.0218(3) 0.0017(3) 0.0054(2) -0.0023(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 N1 1.479(8) yes C1 P1 1.821(8) yes C1 H1A 0.94(9) ? C1 H1B 1.01(9) ? C2 N2 1.486(8) yes C2 P1 1.799(7) yes C2 H2A 0.98(9) ? C2 H2B 0.97(10) ? C3 N3 1.495(9) yes C3 P1 1.825(8) yes C3 H3A 0.96(10) ? C3 H3B 0.96(11) ? C4 N3 1.496(9) yes C4 H4A 0.9800 ? C4 H4B 0.9800 ? C4 H4C 0.9800 ? C12 N1 1.462(9) yes C12 N2 1.467(10) yes C12 H12A 0.92(11) ? C12 H12B 0.90(11) ? C23 N2 1.440(9) yes C23 N3 1.550(9) yes C23 H23A 0.99(10) ? C23 H23B 0.99(10) ? C31 N1 1.441(9) yes C31 N3 1.551(9) yes C31 H31A 0.97(10) ? C31 H31B 1.06(10) ? O1 P1 1.483(5) yes I1 I3 2.9067(8) yes I1 I2 2.9127(7) yes 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 N1 C1 P1 107.9(5) ? N1 C1 H1A 109(5) ? P1 C1 H1A 107(6) ? N1 C1 H1B 118(5) ? P1 C1 H1B 109(5) ? H1A C1 H1B 105(7) ? N2 C2 P1 109.3(5) ? N2 C2 H2A 116(5) ? P1 C2 H2A 106(5) ? N2 C2 H2B 107(5) ? P1 C2 H2B 114(5) ? H2A C2 H2B 104(7) ? N3 C3 P1 110.8(5) ? N3 C3 H3A 112(6) ? P1 C3 H3A 109(6) ? N3 C3 H3B 106(6) ? P1 C3 H3B 110(6) ? H3A C3 H3B 109(8) ? N3 C4 H4A 109.5 ? N3 C4 H4B 109.5 ? H4A C4 H4B 109.5 ? N3 C4 H4C 109.5 ? H4A C4 H4C 109.5 ? H4B C4 H4C 109.5 ? N1 C12 N2 112.4(5) ? N1 C12 H12A 107(6) ? N2 C12 H12A 111(6) ? N1 C12 H12B 112(6) ? N2 C12 H12B 113(6) ? H12A C12 H12B 100(9) ? N2 C23 N3 111.1(5) ? N2 C23 H23A 108(6) ? N3 C23 H23A 106(6) ? N2 C23 H23B 107(6) ? N3 C23 H23B 107(6) ? H23A C23 H23B 117(8) ? N1 C31 N3 110.8(6) ? N1 C31 H31A 109(6) ? N3 C31 H31A 99(6) ? N1 C31 H31B 108(5) ? N3 C31 H31B 108(5) ? H31A C31 H31B 122(8) ? C31 N1 C12 110.7(6) ? C31 N1 C1 114.0(5) ? C12 N1 C1 112.6(6) ? C23 N2 C12 110.4(6) ? C23 N2 C2 113.9(5) ? C12 N2 C2 111.2(6) ? C4 N3 C3 111.3(6) ? C4 N3 C31 108.6(5) ? C3 N3 C31 110.7(6) ? C4 N3 C23 108.0(6) ? C3 N3 C23 110.4(6) ? C31 N3 C23 107.8(5) ? O1 P1 C2 119.2(3) ? O1 P1 C1 119.3(3) ? C2 P1 C1 101.5(3) ? O1 P1 C3 112.4(3) ? C2 P1 C3 100.5(4) ? C1 P1 C3 100.8(4) ? I3 I1 I2 172.41(2) 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 N3 C31 N1 C12 57.7(7) N3 C31 N1 C1 -70.5(8) N2 C12 N1 C31 -59.3(8) N2 C12 N1 C1 69.6(8) P1 C1 N1 C31 65.5(7) P1 C1 N1 C12 -61.6(7) N3 C23 N2 C12 -57.4(7) N3 C23 N2 C2 68.6(7) N1 C12 N2 C23 59.1(7) N1 C12 N2 C2 -68.4(7) P1 C2 N2 C23 -64.0(7) P1 C2 N2 C12 61.6(6) P1 C3 N3 C4 179.9(5) P1 C3 N3 C31 -59.2(7) P1 C3 N3 C23 60.0(7) N1 C31 N3 C4 -172.0(6) N1 C31 N3 C3 65.6(7) N1 C31 N3 C23 -55.2(7) N2 C23 N3 C4 172.4(6) N2 C23 N3 C3 -65.7(7) N2 C23 N3 C31 55.3(7) N2 C2 P1 O1 174.7(4) N2 C2 P1 C1 -52.0(5) N2 C2 P1 C3 51.4(5) N1 C1 P1 O1 -175.4(4) N1 C1 P1 C2 51.3(6) N1 C1 P1 C3 -51.8(6) N3 C3 P1 O1 179.9(5) N3 C3 P1 C2 -52.2(6) N3 C3 P1 C1 51.8(6) 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 C23 H23A O1 1_655 0.99(10) 2.26(11) 3.161(9) 150(9) C31 H31A O1 1_655 0.97(10) 2.23(10) 3.160(9) 161(8)