Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Jason Lynam' _publ_contact_author_address ; Department of Chemistry University of York Heslington York YO10 5DD UNITED KINGDOM ; _publ_contact_author_email JML12@YORK.AC.UK _publ_section_title ; Nucleophilic Substitution Reactions of the Tricyclic Triphosphorus Cage P3(CBut)2: a Novel Route to Polyphosphorus Phosphenium Salts ; loop_ _publ_author_name 'Jason Lynam' 'Cheryl Fish' 'Michael Green' 'Richard J. Kilby' 'C. Russell' 'Adrian C. Whitwood' ; C.E.Willans ; data_jml0513m _database_code_depnum_ccdc_archive 'CCDC 674710' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H27 P4, 2(C F3 O3 S), Tl' _chemical_formula_sum 'C15 H27 F6 O6 P4 S2 Tl' _chemical_formula_weight 809.74 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' O O 0.0106 0.0060 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 13.6272(13) _cell_length_b 10.5615(10) _cell_length_c 19.5594(19) _cell_angle_alpha 90.00 _cell_angle_beta 94.211(2) _cell_angle_gamma 90.00 _cell_volume 2807.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4659 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 26.98 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.916 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 6.197 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.526 _exptl_absorpt_correction_T_max 0.830 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23539 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 30.06 _reflns_number_total 7993 _reflns_number_gt 5444 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0188P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7993 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0642 _refine_ls_wR_factor_gt 0.0568 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6234(2) 0.4016(3) 0.78452(17) 0.0170(7) Uani 1 1 d . . . C2 C 0.6040(2) 0.3974(3) 0.86030(17) 0.0221(8) Uani 1 1 d . . . C3 C 0.6969(2) 0.3558(4) 0.90301(18) 0.0262(8) Uani 1 1 d . . . H3A H 0.7178 0.2727 0.8872 0.039 Uiso 1 1 calc R . . H3B H 0.6830 0.3503 0.9514 0.039 Uiso 1 1 calc R . . H3C H 0.7494 0.4177 0.8978 0.039 Uiso 1 1 calc R . . C4 C 0.5713(3) 0.5286(4) 0.8831(2) 0.0374(10) Uani 1 1 d . . . H4A H 0.6249 0.5894 0.8790 0.056 Uiso 1 1 calc R . . H4B H 0.5545 0.5247 0.9310 0.056 Uiso 1 1 calc R . . H4C H 0.5135 0.5557 0.8540 0.056 Uiso 1 1 calc R . . C5 C 0.5220(3) 0.3009(4) 0.8700(2) 0.0340(10) Uani 1 1 d . . . H5A H 0.4635 0.3235 0.8404 0.051 Uiso 1 1 calc R . . H5B H 0.5058 0.3012 0.9180 0.051 Uiso 1 1 calc R . . H5C H 0.5445 0.2162 0.8578 0.051 Uiso 1 1 calc R . . C6 C 0.6420(2) 0.4048(3) 0.67086(16) 0.0176(7) Uani 1 1 d . . . C7 C 0.6486(3) 0.4053(3) 0.59363(18) 0.0236(8) Uani 1 1 d . . . C8 C 0.6418(4) 0.5428(4) 0.5681(2) 0.0464(12) Uani 1 1 d . . . H8A H 0.5786 0.5792 0.5790 0.070 Uiso 1 1 calc R . . H8B H 0.6467 0.5446 0.5184 0.070 Uiso 1 1 calc R . . H8C H 0.6956 0.5924 0.5907 0.070 Uiso 1 1 calc R . . C9 C 0.7464(3) 0.3482(3) 0.57558(18) 0.0245(8) Uani 1 1 d . . . H9A H 0.8008 0.3999 0.5958 0.037 Uiso 1 1 calc R . . H9B H 0.7489 0.3463 0.5256 0.037 Uiso 1 1 calc R . . H9C H 0.7522 0.2618 0.5937 0.037 Uiso 1 1 calc R . . C10 C 0.5648(3) 0.3253(5) 0.5596(2) 0.0446(12) Uani 1 1 d . . . H10A H 0.5699 0.2384 0.5770 0.067 Uiso 1 1 calc R . . H10B H 0.5695 0.3249 0.5098 0.067 Uiso 1 1 calc R . . H10C H 0.5014 0.3615 0.5701 0.067 Uiso 1 1 calc R . . C11 C 0.9011(2) 0.3482(3) 0.75504(19) 0.0253(8) Uani 1 1 d . . . H11A H 0.9729 0.3551 0.7615 0.038 Uiso 1 1 calc R . . H11B H 0.8829 0.3049 0.7117 0.038 Uiso 1 1 calc R . . H11C H 0.8766 0.2998 0.7930 0.038 Uiso 1 1 calc R . . C12 C 0.8985(3) 0.5968(3) 0.68743(19) 0.0293(9) Uani 1 1 d . . . H12A H 0.8739 0.6838 0.6893 0.044 Uiso 1 1 calc R . . H12B H 0.8789 0.5601 0.6425 0.044 Uiso 1 1 calc R . . H12C H 0.9704 0.5971 0.6946 0.044 Uiso 1 1 calc R . . C13 C 0.8846(3) 0.5846(4) 0.83136(19) 0.0296(9) Uani 1 1 d . . . H13A H 0.8633 0.5358 0.8702 0.044 Uiso 1 1 calc R . . H13B H 0.8543 0.6688 0.8310 0.044 Uiso 1 1 calc R . . H13C H 0.9564 0.5933 0.8356 0.044 Uiso 1 1 calc R . . C14 C 0.2455(3) 0.0623(4) 0.1297(2) 0.0292(9) Uani 1 1 d . . . C15 C 0.7447(3) 0.5820(4) 0.0850(2) 0.0312(9) Uani 1 1 d . . . F1 F 0.31231(14) -0.0155(2) 0.10698(11) 0.0336(5) Uani 1 1 d . . . F2 F 0.26979(16) 0.1798(2) 0.11146(14) 0.0487(7) Uani 1 1 d . . . F3 F 0.25196(18) 0.0571(3) 0.19766(12) 0.0541(7) Uani 1 1 d . . . F4 F 0.73116(17) 0.6191(3) 0.14839(13) 0.0556(8) Uani 1 1 d . . . F5 F 0.72100(18) 0.6782(2) 0.04347(14) 0.0537(7) Uani 1 1 d . . . F6 F 0.68165(15) 0.4889(2) 0.06890(13) 0.0404(6) Uani 1 1 d . . . O1 O 0.11137(18) -0.1093(2) 0.11366(14) 0.0323(6) Uani 1 1 d . . . O2 O 0.12254(18) 0.0446(3) 0.02227(13) 0.0317(6) Uani 1 1 d . . . O3 O 0.05873(18) 0.1092(2) 0.12920(13) 0.0300(6) Uani 1 1 d . . . O4 O 0.92911(17) 0.6385(2) 0.10509(13) 0.0283(6) Uani 1 1 d . . . O5 O 0.87816(18) 0.5152(3) 0.00466(14) 0.0360(7) Uani 1 1 d . . . O6 O 0.88019(19) 0.4182(3) 0.11742(15) 0.0394(7) Uani 1 1 d . . . P1 P 0.68328(6) 0.52563(8) 0.73535(4) 0.01582(18) Uani 1 1 d . . . P2 P 0.64363(7) 0.26169(9) 0.72797(5) 0.02179(19) Uani 1 1 d . . . P3 P 0.52078(6) 0.38863(10) 0.71339(5) 0.0239(2) Uani 1 1 d . . . P4 P 0.84772(6) 0.50416(8) 0.75313(5) 0.01805(19) Uani 1 1 d . . . S1 S 0.12057(6) 0.02250(8) 0.09485(5) 0.02287(19) Uani 1 1 d . . . S2 S 0.87198(6) 0.53240(9) 0.07736(5) 0.02214(19) Uani 1 1 d . . . Tl1 Tl 0.025813(9) 0.749721(14) -0.002359(7) 0.02393(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0137(15) 0.0182(17) 0.0188(18) 0.0031(14) -0.0004(13) -0.0015(13) C2 0.0204(17) 0.026(2) 0.0204(19) 0.0056(15) 0.0020(14) -0.0031(14) C3 0.0228(18) 0.032(2) 0.024(2) 0.0059(16) 0.0021(15) -0.0076(16) C4 0.053(3) 0.035(2) 0.026(2) 0.0054(18) 0.016(2) 0.012(2) C5 0.0243(19) 0.050(3) 0.028(2) 0.0097(19) 0.0054(17) -0.0047(18) C6 0.0186(16) 0.0172(18) 0.0168(18) -0.0002(13) -0.0002(13) 0.0031(13) C7 0.0265(18) 0.023(2) 0.021(2) -0.0014(15) 0.0002(15) 0.0095(15) C8 0.080(3) 0.041(3) 0.019(2) 0.0107(19) 0.009(2) 0.030(2) C9 0.0274(18) 0.0223(19) 0.024(2) -0.0011(15) 0.0058(15) 0.0028(15) C10 0.029(2) 0.077(4) 0.026(2) -0.023(2) -0.0058(18) 0.006(2) C11 0.0194(17) 0.0221(19) 0.035(2) 0.0013(16) 0.0029(16) 0.0029(14) C12 0.0266(19) 0.024(2) 0.039(2) 0.0052(17) 0.0099(17) -0.0068(16) C13 0.0258(19) 0.028(2) 0.035(2) -0.0071(17) -0.0011(17) -0.0074(16) C14 0.0251(19) 0.028(2) 0.035(2) -0.0076(17) 0.0049(17) -0.0028(16) C15 0.0256(19) 0.032(2) 0.036(2) -0.0077(18) 0.0039(17) -0.0006(17) F1 0.0220(10) 0.0372(14) 0.0419(14) -0.0038(11) 0.0038(10) 0.0054(10) F2 0.0302(13) 0.0268(14) 0.090(2) -0.0088(13) 0.0079(13) -0.0080(10) F3 0.0449(15) 0.088(2) 0.0287(15) -0.0148(14) 0.0006(12) -0.0033(14) F4 0.0327(13) 0.088(2) 0.0481(17) -0.0358(15) 0.0160(12) -0.0051(14) F5 0.0432(15) 0.0378(16) 0.080(2) 0.0122(14) 0.0061(14) 0.0173(12) F6 0.0193(10) 0.0411(15) 0.0606(17) -0.0138(12) 0.0013(11) -0.0037(10) O1 0.0285(14) 0.0176(14) 0.0514(18) -0.0007(12) 0.0084(13) -0.0014(11) O2 0.0272(14) 0.0386(17) 0.0292(16) -0.0003(13) 0.0016(12) 0.0079(12) O3 0.0272(13) 0.0266(15) 0.0379(16) -0.0059(12) 0.0135(12) -0.0013(11) O4 0.0264(13) 0.0246(14) 0.0342(15) -0.0085(12) 0.0048(11) -0.0104(11) O5 0.0269(14) 0.053(2) 0.0288(16) -0.0194(14) 0.0035(12) -0.0020(13) O6 0.0273(14) 0.0257(16) 0.064(2) 0.0128(14) -0.0059(14) -0.0025(12) P1 0.0152(4) 0.0159(4) 0.0164(5) 0.0021(3) 0.0017(3) 0.0026(3) P2 0.0233(4) 0.0176(5) 0.0240(5) -0.0010(4) -0.0016(3) -0.0027(4) P3 0.0148(4) 0.0328(6) 0.0235(5) -0.0004(4) -0.0022(4) -0.0011(4) P4 0.0141(4) 0.0151(4) 0.0250(5) 0.0006(4) 0.0018(4) -0.0007(3) S1 0.0197(4) 0.0194(5) 0.0300(5) -0.0033(4) 0.0054(4) 0.0003(4) S2 0.0184(4) 0.0198(5) 0.0281(5) -0.0065(4) 0.0006(4) -0.0022(4) Tl1 0.02555(7) 0.02002(7) 0.02664(8) -0.00192(7) 0.00464(5) 0.00128(7) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.525(5) . ? C1 P1 1.850(3) . ? C1 P2 1.878(3) . ? C1 P3 1.904(3) . ? C2 C3 1.529(5) . ? C2 C4 1.532(5) . ? C2 C5 1.535(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.520(5) . ? C6 P1 1.852(3) . ? C6 P2 1.879(3) . ? C6 P3 1.911(3) . ? C7 C9 1.527(5) . ? C7 C10 1.533(5) . ? C7 C8 1.537(5) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 P4 1.800(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 P4 1.794(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 P4 1.790(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 F3 1.326(4) . ? C14 F1 1.327(4) . ? C14 F2 1.340(4) . ? C14 S1 1.836(4) . ? C15 F4 1.326(4) . ? C15 F5 1.326(5) . ? C15 F6 1.328(4) . ? C15 S2 1.829(4) . ? O1 S1 1.448(3) . ? O2 S1 1.441(3) . ? O3 S1 1.444(2) . ? O4 S2 1.447(2) . ? O5 S2 1.442(3) . ? O6 S2 1.438(3) . ? P3 P2 2.1475(13) . ? P3 P1 2.6538(12) . ? P1 P4 2.2537(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 P1 129.8(2) . . ? C2 C1 P2 126.4(2) . . ? P1 C1 P2 99.31(16) . . ? C2 C1 P3 122.5(2) . . ? P1 C1 P3 89.96(14) . . ? P2 C1 P3 69.20(12) . . ? C1 C2 C3 110.1(3) . . ? C1 C2 C4 109.4(3) . . ? C3 C2 C4 110.4(3) . . ? C1 C2 C5 108.6(3) . . ? C3 C2 C5 108.8(3) . . ? C4 C2 C5 109.6(3) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 P1 129.6(3) . . ? C7 C6 P2 126.5(2) . . ? P1 C6 P2 99.18(15) . . ? C7 C6 P3 123.3(2) . . ? P1 C6 P3 89.68(14) . . ? P2 C6 P3 69.04(12) . . ? C6 C7 C9 110.2(3) . . ? C6 C7 C10 109.5(3) . . ? C9 C7 C10 108.5(3) . . ? C6 C7 C8 108.6(3) . . ? C9 C7 C8 109.4(3) . . ? C10 C7 C8 110.7(3) . . ? 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 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? P4 C11 H11A 109.5 . . ? P4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? P4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? P4 C12 H12A 109.5 . . ? P4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? P4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? P4 C13 H13A 109.5 . . ? P4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? P4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? F3 C14 F1 108.3(3) . . ? F3 C14 F2 107.8(3) . . ? F1 C14 F2 107.2(3) . . ? F3 C14 S1 110.7(3) . . ? F1 C14 S1 112.0(3) . . ? F2 C14 S1 110.7(3) . . ? F4 C15 F5 107.6(3) . . ? F4 C15 F6 108.0(3) . . ? F5 C15 F6 107.3(3) . . ? F4 C15 S2 111.0(3) . . ? F5 C15 S2 111.0(3) . . ? F6 C15 S2 111.7(3) . . ? C1 P3 C6 72.51(14) . . ? C1 P3 P2 54.83(10) . . ? C6 P3 P2 54.78(10) . . ? C1 P3 P1 44.20(10) . . ? C6 P3 P1 44.27(10) . . ? P2 P3 P1 71.68(4) . . ? C1 P2 C6 73.82(14) . . ? C1 P2 P3 55.98(10) . . ? C6 P2 P3 56.18(10) . . ? C1 P1 C6 75.08(15) . . ? C1 P1 P4 108.65(10) . . ? C6 P1 P4 106.55(11) . . ? C1 P1 P3 45.84(10) . . ? C6 P1 P3 46.05(10) . . ? P4 P1 P3 141.12(5) . . ? C13 P4 C12 104.75(18) . . ? C13 P4 C11 109.20(17) . . ? C12 P4 C11 109.72(17) . . ? C13 P4 P1 107.33(13) . . ? C12 P4 P1 105.42(13) . . ? C11 P4 P1 119.42(12) . . ? O2 S1 O3 114.17(16) . . ? O2 S1 O1 114.48(16) . . ? O3 S1 O1 115.31(16) . . ? O2 S1 C14 104.20(17) . . ? O3 S1 C14 103.84(16) . . ? O1 S1 C14 102.75(17) . . ? O6 S2 O5 115.06(18) . . ? O6 S2 O4 115.29(16) . . ? O5 S2 O4 113.48(16) . . ? O6 S2 C15 103.40(18) . . ? O5 S2 C15 103.97(17) . . ? O4 S2 C15 103.59(16) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag P1 C1 C2 C3 -81.2(4) . . . . ? P2 C1 C2 C3 69.9(4) . . . . ? P3 C1 C2 C3 156.9(2) . . . . ? P1 C1 C2 C4 40.3(4) . . . . ? P2 C1 C2 C4 -168.6(3) . . . . ? P3 C1 C2 C4 -81.7(3) . . . . ? P1 C1 C2 C5 159.8(3) . . . . ? P2 C1 C2 C5 -49.1(4) . . . . ? P3 C1 C2 C5 37.8(4) . . . . ? P1 C6 C7 C9 88.6(4) . . . . ? P2 C6 C7 C9 -61.7(4) . . . . ? P3 C6 C7 C9 -149.0(3) . . . . ? P1 C6 C7 C10 -152.2(3) . . . . ? P2 C6 C7 C10 57.5(4) . . . . ? P3 C6 C7 C10 -29.8(4) . . . . ? P1 C6 C7 C8 -31.1(4) . . . . ? P2 C6 C7 C8 178.6(3) . . . . ? P3 C6 C7 C8 91.2(4) . . . . ? C2 C1 P3 C6 -179.5(3) . . . . ? P1 C1 P3 C6 41.15(13) . . . . ? P2 C1 P3 C6 -58.83(12) . . . . ? C2 C1 P3 P2 -120.7(3) . . . . ? P1 C1 P3 P2 99.98(14) . . . . ? C2 C1 P3 P1 139.3(3) . . . . ? P2 C1 P3 P1 -99.98(14) . . . . ? C7 C6 P3 C1 179.5(3) . . . . ? P1 C6 P3 C1 -41.09(13) . . . . ? P2 C6 P3 C1 58.88(12) . . . . ? C7 C6 P3 P2 120.7(3) . . . . ? P1 C6 P3 P2 -99.97(13) . . . . ? C7 C6 P3 P1 -139.4(3) . . . . ? P2 C6 P3 P1 99.97(13) . . . . ? C2 C1 P2 C6 175.5(3) . . . . ? P1 C1 P2 C6 -26.60(14) . . . . ? P3 C1 P2 C6 59.78(12) . . . . ? C2 C1 P2 P3 115.7(3) . . . . ? P1 C1 P2 P3 -86.38(13) . . . . ? C7 C6 P2 C1 -176.2(3) . . . . ? P1 C6 P2 C1 26.56(14) . . . . ? P3 C6 P2 C1 -59.54(12) . . . . ? C7 C6 P2 P3 -116.7(3) . . . . ? P1 C6 P2 P3 86.10(14) . . . . ? C6 P3 P2 C1 92.72(17) . . . . ? P1 P3 P2 C1 46.32(12) . . . . ? C1 P3 P2 C6 -92.72(17) . . . . ? P1 P3 P2 C6 -46.40(12) . . . . ? C2 C1 P1 C6 -176.4(3) . . . . ? P2 C1 P1 C6 26.84(14) . . . . ? P3 C1 P1 C6 -42.06(13) . . . . ? C2 C1 P1 P4 80.8(3) . . . . ? P2 C1 P1 P4 -75.94(13) . . . . ? P3 C1 P1 P4 -144.84(9) . . . . ? C2 C1 P1 P3 -134.3(4) . . . . ? P2 C1 P1 P3 68.90(13) . . . . ? C7 C6 P1 C1 177.0(3) . . . . ? P2 C6 P1 C1 -26.81(14) . . . . ? P3 C6 P1 C1 41.88(13) . . . . ? C7 C6 P1 P4 -77.6(3) . . . . ? P2 C6 P1 P4 78.62(13) . . . . ? P3 C6 P1 P4 147.32(9) . . . . ? C7 C6 P1 P3 135.1(4) . . . . ? P2 C6 P1 P3 -68.69(13) . . . . ? C6 P3 P1 C1 -115.9(2) . . . . ? P2 P3 P1 C1 -58.00(15) . . . . ? C1 P3 P1 C6 115.9(2) . . . . ? P2 P3 P1 C6 57.95(14) . . . . ? C1 P3 P1 P4 60.39(16) . . . . ? C6 P3 P1 P4 -55.56(16) . . . . ? P2 P3 P1 P4 2.39(8) . . . . ? C1 P1 P4 C13 -83.87(18) . . . . ? C6 P1 P4 C13 -163.32(17) . . . . ? P3 P1 P4 C13 -125.04(15) . . . . ? C1 P1 P4 C12 164.86(17) . . . . ? C6 P1 P4 C12 85.41(18) . . . . ? P3 P1 P4 C12 123.69(15) . . . . ? C1 P1 P4 C11 40.98(19) . . . . ? C6 P1 P4 C11 -38.46(19) . . . . ? P3 P1 P4 C11 -0.19(17) . . . . ? F3 C14 S1 O2 174.3(3) . . . . ? F1 C14 S1 O2 -64.7(3) . . . . ? F2 C14 S1 O2 54.9(3) . . . . ? F3 C14 S1 O3 54.5(3) . . . . ? F1 C14 S1 O3 175.5(3) . . . . ? F2 C14 S1 O3 -65.0(3) . . . . ? F3 C14 S1 O1 -66.0(3) . . . . ? F1 C14 S1 O1 55.0(3) . . . . ? F2 C14 S1 O1 174.6(3) . . . . ? F4 C15 S2 O6 68.4(3) . . . . ? F5 C15 S2 O6 -171.9(3) . . . . ? F6 C15 S2 O6 -52.2(3) . . . . ? F4 C15 S2 O5 -171.1(3) . . . . ? F5 C15 S2 O5 -51.4(3) . . . . ? F6 C15 S2 O5 68.3(3) . . . . ? F4 C15 S2 O4 -52.2(3) . . . . ? F5 C15 S2 O4 67.4(3) . . . . ? F6 C15 S2 O4 -172.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 1.250 _refine_diff_density_min -0.839 _refine_diff_density_rms 0.131 # Attachment 'jml0536m.cif' data_jml0536m _database_code_depnum_ccdc_archive 'CCDC 674711' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H18 I3 P3' _chemical_formula_sum 'C10 H18 I3 P3' _chemical_formula_weight 611.85 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' P P 0.1023 0.0942 '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' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(3)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 9.7125(6) _cell_length_b 9.7125(6) _cell_length_c 14.1758(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1158.08(17) _cell_formula_units_Z 2 _cell_measurement_temperature 383(2) _cell_measurement_reflns_used 2161 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 22.28 _exptl_crystal_description needle _exptl_crystal_colour pale _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.755 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 4.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 383(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5195 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 22.49 _reflns_number_total 538 _reflns_number_gt 498 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. The structure contains a significant solvent accessible void which is believed to partially occupied by disordered iodine molecules. This was modelled using squeeze after all other atoms were located (see below). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0118P)^2^+3.5921P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 538 _refine_ls_number_parameters 32 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0548 _refine_ls_wR_factor_gt 0.0535 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3333 0.6667 0.8293(5) 0.0307(18) Uani 1 3 d S . . C2 C 0.3333 0.6667 0.9372(5) 0.038(2) Uani 1 3 d S . . C3 C 0.2654(7) 0.7689(6) 0.9730(3) 0.0462(13) Uani 1 1 d . . . H3A H 0.1567 0.7231 0.9530 0.067(18) Uiso 1 1 calc R . . H3B H 0.3264 0.8744 0.9478 0.045(14) Uiso 1 1 calc R . . H3C H 0.2703 0.7734 1.0406 0.076(19) Uiso 1 1 calc R . . I1 I -0.06690(6) 0.43401(7) 0.7500 0.0539(2) Uani 1 2 d S . . P1 P 0.1952(2) 0.6940(2) 0.7500 0.0375(4) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.035(3) 0.035(3) 0.022(4) 0.000 0.000 0.0176(14) C2 0.049(3) 0.049(3) 0.016(4) 0.000 0.000 0.0243(16) C3 0.064(4) 0.060(4) 0.020(3) 0.000(2) 0.007(3) 0.035(3) I1 0.0378(3) 0.0789(4) 0.0283(3) 0.000 0.000 0.0167(3) P1 0.0445(11) 0.0535(12) 0.0200(9) 0.000 0.000 0.0287(10) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.529(11) . ? C1 P1 1.868(5) . ? C1 P1 1.868(5) 3_565 ? C1 P1 1.868(5) 2_665 ? C2 C3 1.528(5) . ? C2 C3 1.528(5) 3_565 ? C2 C3 1.528(5) 2_665 ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? I1 P1 2.536(2) . ? P1 C1 1.868(5) 10_557 ? P1 P1 2.585(3) 3_565 ? P1 P1 2.585(3) 2_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 P1 126.99(19) . . ? C2 C1 P1 126.99(19) . 3_565 ? P1 C1 P1 87.5(3) . 3_565 ? C2 C1 P1 126.99(19) . 2_665 ? P1 C1 P1 87.5(3) . 2_665 ? P1 C1 P1 87.5(3) 3_565 2_665 ? C3 C2 C3 109.5(3) . 3_565 ? C3 C2 C3 109.5(3) . 2_665 ? C3 C2 C3 109.5(3) 3_565 2_665 ? C3 C2 C1 109.4(3) . . ? C3 C2 C1 109.4(3) 3_565 . ? C3 C2 C1 109.4(3) 2_665 . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 P1 C1 74.0(4) . 10_557 ? C1 P1 I1 107.03(9) . . ? C1 P1 I1 107.03(9) 10_557 . ? C1 P1 P1 46.24(14) . 3_565 ? C1 P1 P1 46.24(14) 10_557 3_565 ? I1 P1 P1 141.52(10) . 3_565 ? C1 P1 P1 46.24(14) . 2_665 ? C1 P1 P1 46.24(14) 10_557 2_665 ? I1 P1 P1 81.52(10) . 2_665 ? P1 P1 P1 60.0 3_565 2_665 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag P1 C1 C2 C3 -27.7(2) . . . . ? P1 C1 C2 C3 92.3(2) 3_565 . . . ? P1 C1 C2 C3 -147.7(2) 2_665 . . . ? P1 C1 C2 C3 -147.7(2) . . . 3_565 ? P1 C1 C2 C3 -27.7(2) 3_565 . . 3_565 ? P1 C1 C2 C3 92.3(2) 2_665 . . 3_565 ? P1 C1 C2 C3 92.3(2) . . . 2_665 ? P1 C1 C2 C3 -147.7(2) 3_565 . . 2_665 ? P1 C1 C2 C3 -27.7(2) 2_665 . . 2_665 ? C2 C1 P1 C1 180.000(4) . . . 10_557 ? P1 C1 P1 C1 43.81(12) 3_565 . . 10_557 ? P1 C1 P1 C1 -43.81(13) 2_665 . . 10_557 ? C2 C1 P1 I1 -76.66(9) . . . . ? P1 C1 P1 I1 147.16(9) 3_565 . . . ? P1 C1 P1 I1 59.5(2) 2_665 . . . ? C2 C1 P1 P1 136.19(13) . . . 3_565 ? P1 C1 P1 P1 -87.6(3) 2_665 . . 3_565 ? C2 C1 P1 P1 -136.19(13) . . . 2_665 ? P1 C1 P1 P1 87.6(3) 3_565 . . 2_665 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.781 _refine_diff_density_min -0.981 _refine_diff_density_rms 0.077 # SQUEEZE RESULTS loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 -0.004 370.5 83.7 _platon_squeeze_details ; ;