############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # ############################################################################## data_I _audit_creation_method SHELXL97 _chemical_name_systematic ; 1-Methyl-1-azonia-3,5-diaza-7-phosphatricyclo[3.3.1.1]decane 7-oxide triiodide ; _chemical_name_common ? _chemical_formula_moiety 'C7 H15 N3 O P + , I3 -' _chemical_formula_sum 'C7 H15 Cu0 I3 N3 O P' _chemical_formula_iupac 'C7 H15 N3 O P + , I3 -' _chemical_formula_weight 568.89 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_hall -P2yn 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' _cell_length_a 7.1570(8) _cell_length_b 8.2257(8) _cell_length_c 25.903(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.472(7) _cell_angle_gamma 90.00 _cell_volume 1523.5(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2835 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.93 _cell_measurement_temperature 150(2) _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.480 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 6.244 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.4974 _exptl_absorpt_correction_T_max 0.5740 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11526 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2789 _reflns_number_gt 2214 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_gt 0.0978 _refine_ls_wR_factor_ref 0.1023 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _refine_ls_number_reflns 2789 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0450P)^2^+6.2243P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.003 _refine_diff_density_max 2.441 _refine_diff_density_min -1.033 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'SMART (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'WinGX (Version 1.70.01; Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' 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 _atom_site_disorder_assembly _atom_site_disorder_group 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) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 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_site_symmetry_1 _geom_angle_site_symmetry_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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag 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) data_global _journal_date_recd_electronic 2008-01-07 _journal_date_accepted 2008-01-14 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2008 _journal_volume 64 _journal_issue 2 _journal_page_first o496 _journal_page_last o497 _journal_paper_category QO _journal_coeditor_code KP2159 _publ_contact_author_name 'M. Fatima C. Guedes da Silva' _publ_contact_author_address ; Centro de Quimica Estrutural Complexo Interdisciplinar Instituto Superior Tecnico TU Lisbon Avenida Rovisco Pais 1049-001 Lisbon Portugal ; _publ_contact_author_email fatima.guedes@ist.utl.pt _publ_contact_author_fax '+351-21-846-4455' _publ_contact_author_phone '+351-21-841-9235' _publ_section_title ; 1-Methyl-1-azonia-3,5-diaza-7-phosphatricyclo[3.3.1.1]decane 7-oxide triiodide ; loop_ _publ_author_name _publ_author_address 'Kirillov, Alexander M.' ; Centro de Qu\'imica Estrutural Complexo Interdisciplinar Instituto Superior T\'ecnico TU Lisbon Avenida Rovisco Pais 1049-001 Lisbon Portugal ; 'Smole\'nski, Piotr' ; Centro de Qu\'imica Estrutural Complexo Interdisciplinar Instituto Superior T\'ecnico TU Lisbon Avenida Rovisco Pais 1049-001 Lisbon Portugal ; 'Guedes da Silva, M. F\'atima C.' ; Centro de Qu\'imica Estrutural Complexo Interdisciplinar Instituto Superior T\'ecnico TU Lisbon Avenida Rovisco Pais 1049-001 Lisbon Portugal and Universidade Lus\'ofona de Humanidades e Tecnologias ULHT Lisbon Avenida do Campo Grande 376 1749-024 Lisbon Portugal ; 'Pombeiro, Armando J. L.' ; Centro de Qu\'imica Estrutural Complexo Interdisciplinar Instituto Superior T\'ecnico TU Lisbon Avenida Rovisco Pais 1049-001 Lisbon Portugal ;