Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Louis Rendina' _publ_contact_author_address ; Department of Chemistry The University of Sydney Sydney NSW 2006 AUSTRALIA ; _publ_contact_author_email RENDINA@CHEM.USYD.EDU.AU _publ_section_title ; Dicarba-closo-dodecaborane(12) Derivatives of Phosphonium Salts: Easy Formation of Nido-Carborane Phosphonium Zwitterions ; loop_ _publ_author_name 'Louis Rendina' 'Jack K. Clegg' 'Joseph A. Ioppolo' data_lj144sad _database_code_depnum_ccdc_archive 'CCDC 629314' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H24 B9 P' _chemical_formula_sum 'C15 H24 B9 P' _chemical_formula_weight 332.60 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' B B 0.0013 0.0007 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' _intl_tables_symmetry_no 14 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 11.4316(14) _cell_length_b 9.4232(10) _cell_length_c 17.547(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.805(6) _cell_angle_gamma 90.00 _cell_volume 1843.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5545 _cell_measurement_theta_min 2.6605 _cell_measurement_theta_max 30.478 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.314 _exptl_crystal_size_mid 0.290 _exptl_crystal_size_min 0.157 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.750 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 37976 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 30.64 _reflns_number_total 5637 _reflns_number_gt 4587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) POV-Ray 3.5 (Cason, 2002) WebLab ViewerPro 3.7 (Molecular Simulations, 2000) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0632P)^2^+0.8298P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5637 _refine_ls_number_parameters 242 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1318 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.001 _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 0.83316(11) -0.00435(14) 0.44965(7) 0.0184(2) Uani 1 1 d . . . H1 H 0.8819(15) 0.0676(19) 0.4786(10) 0.022 Uiso 1 1 d . . . C2 C 0.70448(10) 0.04365(14) 0.40580(7) 0.0163(2) Uani 1 1 d . . . C3 C 0.51748(12) 0.26190(16) 0.37286(8) 0.0239(3) Uani 1 1 d . . . H3A H 0.4768 0.2136 0.4091 0.036 Uiso 1 1 calc R . . H3B H 0.4871 0.2253 0.3199 0.036 Uiso 1 1 calc R . . H3C H 0.5020 0.3641 0.3737 0.036 Uiso 1 1 calc R . . C4 C 0.73161(11) 0.31713(14) 0.49405(7) 0.0178(2) Uani 1 1 d . . . C5 C 0.84755(12) 0.37303(15) 0.51308(8) 0.0222(3) Uani 1 1 d . . . H5 H 0.8986 0.3651 0.4773 0.027 Uiso 1 1 calc R . . C6 C 0.88814(14) 0.44055(17) 0.58482(8) 0.0273(3) Uani 1 1 d . . . H6 H 0.9671 0.4783 0.5980 0.033 Uiso 1 1 calc R . . C7 C 0.81373(15) 0.45277(16) 0.63681(8) 0.0280(3) Uani 1 1 d . . . H7 H 0.8414 0.5002 0.6852 0.034 Uiso 1 1 calc R . . C8 C 0.69877(14) 0.39608(18) 0.61859(8) 0.0290(3) Uani 1 1 d . . . H8 H 0.6485 0.4040 0.6548 0.035 Uiso 1 1 calc R . . C9 C 0.65708(13) 0.32784(17) 0.54750(8) 0.0247(3) Uani 1 1 d . . . H9 H 0.5786 0.2887 0.5352 0.030 Uiso 1 1 calc R . . C10 C 0.74837(11) 0.30231(14) 0.32933(7) 0.0174(2) Uani 1 1 d . . . C11 C 0.86261(12) 0.25531(15) 0.32397(8) 0.0219(3) Uani 1 1 d . . . H11 H 0.9019 0.1833 0.3581 0.026 Uiso 1 1 calc R . . C12 C 0.91833(13) 0.31425(17) 0.26851(9) 0.0268(3) Uani 1 1 d . . . H12 H 0.9959 0.2827 0.2649 0.032 Uiso 1 1 calc R . . C13 C 0.86053(14) 0.41948(17) 0.21820(8) 0.0282(3) Uani 1 1 d . . . H13 H 0.8990 0.4600 0.1806 0.034 Uiso 1 1 calc R . . C14 C 0.74753(14) 0.46497(16) 0.22284(8) 0.0275(3) Uani 1 1 d . . . H14 H 0.7082 0.5361 0.1880 0.033 Uiso 1 1 calc R . . C15 C 0.69078(13) 0.40728(15) 0.27814(8) 0.0230(3) Uani 1 1 d . . . H15 H 0.6131 0.4391 0.2811 0.028 Uiso 1 1 calc R . . B1 B 0.88515(13) -0.12831(17) 0.40182(9) 0.0213(3) Uani 1 1 d D . . H1A H 0.9825(15) -0.1378(19) 0.4026(10) 0.026 Uiso 1 1 d . . . H1B H 0.8312(10) -0.0945(8) 0.3447(4) 0.026 Uiso 1 1 d D . . B2 B 0.76359(14) -0.17188(17) 0.31601(9) 0.0220(3) Uani 1 1 d D . . H2 H 0.7759(16) -0.2206(19) 0.2609(11) 0.026 Uiso 1 1 d . . . B3 B 0.65000(13) -0.04256(16) 0.32523(8) 0.0187(3) Uani 1 1 d . . . H3 H 0.5915(15) 0.0127(18) 0.2781(10) 0.022 Uiso 1 1 d . . . B4 B 0.83161(13) -0.17075(17) 0.48836(9) 0.0218(3) Uani 1 1 d . . . H4 H 0.8916 -0.2124 0.5431 0.026 Uiso 1 1 calc R . . B5 B 0.78797(14) -0.27521(17) 0.40331(9) 0.0217(3) Uani 1 1 d . . . H5A H 0.8209 -0.3869 0.4019 0.026 Uiso 1 1 calc R . . B6 B 0.63749(14) -0.21856(17) 0.35501(9) 0.0213(3) Uani 1 1 d . . . H6A H 0.5681 -0.2923 0.3212 0.026 Uiso 1 1 calc R . . B7 B 0.59497(13) -0.08112(17) 0.41121(8) 0.0197(3) Uani 1 1 d . . . H7A H 0.4998 -0.0620 0.4151 0.024 Uiso 1 1 calc R . . B8 B 0.71654(13) -0.04819(17) 0.49290(8) 0.0202(3) Uani 1 1 d . . . H8A H 0.7016 -0.0049 0.5494 0.024 Uiso 1 1 calc R . . B9 B 0.68053(13) -0.22452(17) 0.46015(9) 0.0212(3) Uani 1 1 d . . . H9A H 0.6411 -0.3032 0.4952 0.025 Uiso 1 1 calc R . . P1 P 0.67603(3) 0.23024(4) 0.401900(18) 0.01623(10) 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 0.0161(5) 0.0198(6) 0.0167(5) 0.0007(5) -0.0020(4) -0.0017(4) C2 0.0142(5) 0.0188(6) 0.0139(5) 0.0003(4) -0.0013(4) -0.0008(4) C3 0.0173(6) 0.0303(7) 0.0221(6) 0.0000(5) 0.0003(5) 0.0039(5) C4 0.0209(6) 0.0166(6) 0.0148(5) -0.0009(4) 0.0015(4) 0.0011(4) C5 0.0231(6) 0.0246(7) 0.0181(6) -0.0024(5) 0.0026(5) -0.0024(5) C6 0.0295(7) 0.0272(7) 0.0222(6) -0.0045(5) -0.0007(5) -0.0048(6) C7 0.0398(8) 0.0242(7) 0.0173(6) -0.0049(5) 0.0006(5) 0.0007(6) C8 0.0363(8) 0.0326(8) 0.0196(6) -0.0034(6) 0.0093(6) 0.0032(6) C9 0.0240(6) 0.0301(7) 0.0205(6) -0.0029(5) 0.0059(5) -0.0014(5) C10 0.0193(5) 0.0174(6) 0.0139(5) -0.0013(4) 0.0002(4) -0.0009(4) C11 0.0202(6) 0.0236(7) 0.0207(6) 0.0015(5) 0.0021(5) 0.0002(5) C12 0.0252(6) 0.0301(8) 0.0258(7) -0.0014(6) 0.0074(5) -0.0031(6) C13 0.0377(8) 0.0274(7) 0.0208(6) -0.0009(5) 0.0095(6) -0.0071(6) C14 0.0389(8) 0.0252(7) 0.0173(6) 0.0044(5) 0.0039(5) 0.0018(6) C15 0.0266(6) 0.0228(7) 0.0180(6) 0.0012(5) 0.0018(5) 0.0037(5) B1 0.0180(6) 0.0233(7) 0.0214(7) 0.0024(5) 0.0019(5) 0.0010(5) B2 0.0266(7) 0.0214(7) 0.0173(6) -0.0021(5) 0.0037(5) -0.0026(6) B3 0.0198(6) 0.0203(7) 0.0135(6) -0.0002(5) -0.0015(5) -0.0022(5) B4 0.0210(6) 0.0233(7) 0.0181(6) 0.0045(5) -0.0019(5) 0.0001(5) B5 0.0223(7) 0.0195(7) 0.0223(7) 0.0020(5) 0.0027(5) -0.0004(5) B6 0.0223(7) 0.0205(7) 0.0185(6) 0.0001(5) -0.0009(5) -0.0041(5) B7 0.0167(6) 0.0226(7) 0.0186(6) 0.0022(5) 0.0011(5) -0.0027(5) B8 0.0213(6) 0.0247(7) 0.0135(6) 0.0024(5) 0.0012(5) -0.0008(5) B9 0.0206(6) 0.0232(7) 0.0186(6) 0.0046(5) 0.0021(5) -0.0022(5) P1 0.01515(15) 0.01860(17) 0.01344(15) -0.00031(11) -0.00005(11) 0.00069(11) _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 1.5680(17) . ? C1 B1 1.626(2) . ? C1 B4 1.711(2) . ? C1 B8 1.7240(19) . ? C1 H1 0.950(18) . ? C2 B3 1.6297(18) . ? C2 B8 1.7351(19) . ? C2 B7 1.7354(19) . ? C2 P1 1.7867(14) . ? C3 P1 1.7957(14) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.3962(18) . ? C4 C9 1.4036(18) . ? C4 P1 1.7981(13) . ? C5 C6 1.3949(19) . ? C5 H5 0.9500 . ? C6 C7 1.383(2) . ? C6 H6 0.9500 . ? C7 C8 1.389(2) . ? C7 H7 0.9500 . ? C8 C9 1.390(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C15 1.3988(18) . ? C10 C11 1.4018(18) . ? C10 P1 1.7982(13) . ? C11 C12 1.3914(19) . ? C11 H11 0.9500 . ? C12 C13 1.393(2) . ? C12 H12 0.9500 . ? C13 C14 1.380(2) . ? C13 H13 0.9500 . ? C14 C15 1.3918(19) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? B1 B5 1.779(2) . ? B1 B4 1.803(2) . ? B1 B2 1.854(2) . ? B1 H1A 1.113(17) . ? B1 H1B 1.101(8) . ? B2 B6 1.782(2) . ? B2 B5 1.784(2) . ? B2 B3 1.814(2) . ? B2 H1B 1.100(9) . ? B2 H2 1.107(18) . ? B3 B6 1.754(2) . ? B3 B7 1.796(2) . ? B3 H3 1.075(17) . ? B4 B9 1.762(2) . ? B4 B5 1.765(2) . ? B4 B8 1.766(2) . ? B4 H4 1.1200 . ? B5 B9 1.810(2) . ? B5 B6 1.821(2) . ? B5 H5A 1.1200 . ? B6 B7 1.760(2) . ? B6 B9 1.802(2) . ? B6 H6A 1.1200 . ? B7 B9 1.774(2) . ? B7 B8 1.789(2) . ? B7 H7A 1.1200 . ? B8 B9 1.776(2) . ? B8 H8A 1.1200 . ? B9 H9A 1.1200 . ? 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 B1 111.37(10) . . ? C2 C1 B4 111.60(10) . . ? B1 C1 B4 65.38(9) . . ? C2 C1 B8 63.41(8) . . ? B1 C1 B8 117.51(11) . . ? B4 C1 B8 61.87(9) . . ? C2 C1 H1 115.6(10) . . ? B1 C1 H1 123.4(10) . . ? B4 C1 H1 119.9(10) . . ? B8 C1 H1 110.8(10) . . ? C1 C2 B3 114.74(10) . . ? C1 C2 B8 62.69(8) . . ? B3 C2 B8 117.13(11) . . ? C1 C2 B7 112.79(10) . . ? B3 C2 B7 64.41(8) . . ? B8 C2 B7 62.05(8) . . ? C1 C2 P1 116.46(9) . . ? B3 C2 P1 115.21(9) . . ? B8 C2 P1 120.18(9) . . ? B7 C2 P1 122.78(9) . . ? P1 C3 H3A 109.5 . . ? P1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? P1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C9 119.85(12) . . ? C5 C4 P1 120.96(10) . . ? C9 C4 P1 119.20(10) . . ? C6 C5 C4 119.75(13) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 C5 120.20(14) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.34(13) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C9 120.21(13) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C4 119.65(13) . . ? C8 C9 H9 120.2 . . ? C4 C9 H9 120.2 . . ? C15 C10 C11 119.56(12) . . ? C15 C10 P1 119.80(10) . . ? C11 C10 P1 120.64(10) . . ? C12 C11 C10 119.90(13) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.06(13) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 120.16(13) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.44(14) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C10 119.88(13) . . ? C14 C15 H15 120.1 . . ? C10 C15 H15 120.1 . . ? C1 B1 B5 104.51(10) . . ? C1 B1 B4 59.57(9) . . ? B5 B1 B4 59.03(9) . . ? C1 B1 B2 106.52(10) . . ? B5 B1 B2 58.77(8) . . ? B4 B1 B2 107.54(10) . . ? C1 B1 H1A 122.0(9) . . ? B5 B1 H1A 124.3(9) . . ? B4 B1 H1A 119.7(9) . . ? B2 B1 H1A 124.0(9) . . ? C1 B1 H1B 93.8(8) . . ? B4 B1 H1B 127.2(8) . . ? B2 B1 H1B 32.6(5) . . ? H1A B1 H1B 113.1(12) . . ? B6 B2 B5 61.41(9) . . ? B6 B2 B3 58.38(9) . . ? B5 B2 B3 105.59(10) . . ? B6 B2 B1 105.50(10) . . ? B5 B2 B1 58.49(8) . . ? B3 B2 B1 101.61(10) . . ? B6 B2 H1B 122.2(8) . . ? B5 B2 H1B 90.5(2) . . ? B3 B2 H1B 87.6(8) . . ? B6 B2 H2 120.2(9) . . ? B5 B2 H2 119.9(9) . . ? B3 B2 H2 126.1(9) . . ? B1 B2 H2 125.7(9) . . ? H1B B2 H2 117.6(12) . . ? C2 B3 B6 104.69(10) . . ? C2 B3 B7 60.65(8) . . ? B6 B3 B7 59.44(9) . . ? C2 B3 B2 105.59(10) . . ? B6 B3 B2 59.91(9) . . ? B7 B3 B2 109.27(10) . . ? C2 B3 H3 118.6(9) . . ? B6 B3 H3 127.5(9) . . ? B7 B3 H3 118.0(9) . . ? B2 B3 H3 126.3(9) . . ? C1 B4 B9 104.34(10) . . ? C1 B4 B5 101.62(10) . . ? B9 B4 B5 61.73(9) . . ? C1 B4 B8 59.44(8) . . ? B9 B4 B8 60.47(9) . . ? B5 B4 B8 109.22(10) . . ? C1 B4 B1 55.04(8) . . ? B9 B4 B1 108.76(10) . . ? B5 B4 B1 59.79(9) . . ? B8 B4 B1 106.75(10) . . ? C1 B4 H4 127.1 . . ? B9 B4 H4 121.1 . . ? B5 B4 H4 122.3 . . ? B8 B4 H4 120.8 . . ? B1 B4 H4 122.8 . . ? B4 B5 B1 61.18(9) . . ? B4 B5 B2 112.50(11) . . ? B1 B5 B2 62.73(9) . . ? B4 B5 B9 59.06(9) . . ? B1 B5 B9 107.76(11) . . ? B2 B5 B9 109.47(11) . . ? B4 B5 B6 106.91(11) . . ? B1 B5 B6 107.08(11) . . ? B2 B5 B6 59.25(9) . . ? B9 B5 B6 59.51(8) . . ? B4 B5 H5A 120.6 . . ? B1 B5 H5A 121.1 . . ? B2 B5 H5A 118.9 . . ? B9 B5 H5A 122.2 . . ? B6 B5 H5A 123.5 . . ? B3 B6 B7 61.46(9) . . ? B3 B6 B2 61.71(9) . . ? B7 B6 B2 112.38(11) . . ? B3 B6 B9 108.22(11) . . ? B7 B6 B9 59.73(9) . . ? B2 B6 B9 109.89(10) . . ? B3 B6 B5 106.55(10) . . ? B7 B6 B5 107.73(10) . . ? B2 B6 B5 59.34(9) . . ? B9 B6 B5 59.93(8) . . ? B3 B6 H6A 121.6 . . ? B7 B6 H6A 120.1 . . ? B2 B6 H6A 119.2 . . ? B9 B6 H6A 121.5 . . ? B5 B6 H6A 123.3 . . ? C2 B7 B6 100.12(10) . . ? C2 B7 B9 102.44(10) . . ? B6 B7 B9 61.30(9) . . ? C2 B7 B8 58.97(8) . . ? B6 B7 B8 108.34(10) . . ? B9 B7 B8 59.81(9) . . ? C2 B7 B3 54.94(7) . . ? B6 B7 B3 59.10(8) . . ? B9 B7 B3 107.61(10) . . ? B8 B7 B3 106.47(10) . . ? C2 B7 H7A 128.1 . . ? B6 B7 H7A 123.1 . . ? B9 B7 H7A 122.1 . . ? B8 B7 H7A 121.0 . . ? B3 B7 H7A 123.0 . . ? C1 B8 C2 53.91(7) . . ? C1 B8 B4 58.69(8) . . ? C2 B8 B4 101.59(10) . . ? C1 B8 B9 103.18(10) . . ? C2 B8 B9 102.36(10) . . ? B4 B8 B9 59.67(9) . . ? C1 B8 B7 103.18(9) . . ? C2 B8 B7 58.98(8) . . ? B4 B8 B7 107.74(11) . . ? B9 B8 B7 59.69(9) . . ? C1 B8 H8A 126.0 . . ? C2 B8 H8A 126.9 . . ? B4 B8 H8A 122.7 . . ? B9 B8 H8A 123.9 . . ? B7 B8 H8A 121.9 . . ? B4 B9 B7 108.53(11) . . ? B4 B9 B8 59.86(9) . . ? B7 B9 B8 60.50(9) . . ? B4 B9 B6 107.87(10) . . ? B7 B9 B6 58.97(8) . . ? B8 B9 B6 107.05(10) . . ? B4 B9 B5 59.20(9) . . ? B7 B9 B5 107.63(10) . . ? B8 B9 B5 106.75(10) . . ? B6 B9 B5 60.56(9) . . ? B4 B9 H9A 121.7 . . ? B7 B9 H9A 121.6 . . ? B8 B9 H9A 122.3 . . ? B6 B9 H9A 122.1 . . ? B5 B9 H9A 122.2 . . ? C2 P1 C3 109.76(6) . . ? C2 P1 C4 112.87(6) . . ? C3 P1 C4 108.23(6) . . ? C2 P1 C10 106.88(6) . . ? C3 P1 C10 109.27(6) . . ? C4 P1 C10 109.79(6) . . ? 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 B1 C1 C2 B3 1.94(15) . . . . ? B4 C1 C2 B3 -69.03(13) . . . . ? B8 C1 C2 B3 -109.09(12) . . . . ? B1 C1 C2 B8 111.03(12) . . . . ? B4 C1 C2 B8 40.06(10) . . . . ? B1 C1 C2 B7 73.14(13) . . . . ? B4 C1 C2 B7 2.18(14) . . . . ? B8 C1 C2 B7 -37.88(10) . . . . ? B1 C1 C2 P1 -136.95(10) . . . . ? B4 C1 C2 P1 152.09(9) . . . . ? B8 C1 C2 P1 112.02(10) . . . . ? C9 C4 C5 C6 -0.7(2) . . . . ? P1 C4 C5 C6 179.67(11) . . . . ? C4 C5 C6 C7 -0.3(2) . . . . ? C5 C6 C7 C8 1.0(2) . . . . ? C6 C7 C8 C9 -0.7(2) . . . . ? C7 C8 C9 C4 -0.3(2) . . . . ? C5 C4 C9 C8 1.0(2) . . . . ? P1 C4 C9 C8 -179.36(12) . . . . ? C15 C10 C11 C12 0.7(2) . . . . ? P1 C10 C11 C12 -178.70(11) . . . . ? C10 C11 C12 C13 -0.2(2) . . . . ? C11 C12 C13 C14 -0.4(2) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C13 C14 C15 C10 -0.1(2) . . . . ? C11 C10 C15 C14 -0.5(2) . . . . ? P1 C10 C15 C14 178.87(11) . . . . ? C2 C1 B1 B5 -65.03(13) . . . . ? B4 C1 B1 B5 39.78(9) . . . . ? B8 C1 B1 B5 5.21(14) . . . . ? C2 C1 B1 B4 -104.81(11) . . . . ? B8 C1 B1 B4 -34.58(10) . . . . ? C2 C1 B1 B2 -3.83(14) . . . . ? B4 C1 B1 B2 100.98(11) . . . . ? B8 C1 B1 B2 66.40(13) . . . . ? C1 B1 B2 B6 -56.03(13) . . . . ? B5 B1 B2 B6 41.20(10) . . . . ? B4 B1 B2 B6 6.56(14) . . . . ? C1 B1 B2 B5 -97.23(11) . . . . ? B4 B1 B2 B5 -34.63(10) . . . . ? C1 B1 B2 B3 4.07(13) . . . . ? B5 B1 B2 B3 101.30(11) . . . . ? B4 B1 B2 B3 66.66(12) . . . . ? C1 C2 B3 B6 63.25(13) . . . . ? B8 C2 B3 B6 -7.39(14) . . . . ? B7 C2 B3 B6 -41.36(10) . . . . ? P1 C2 B3 B6 -157.34(9) . . . . ? C1 C2 B3 B7 104.61(11) . . . . ? B8 C2 B3 B7 33.98(10) . . . . ? P1 C2 B3 B7 -115.98(10) . . . . ? C1 C2 B3 B2 0.96(14) . . . . ? B8 C2 B3 B2 -69.68(13) . . . . ? B7 C2 B3 B2 -103.66(11) . . . . ? P1 C2 B3 B2 140.36(9) . . . . ? B6 B2 B3 C2 98.20(11) . . . . ? B5 B2 B3 C2 57.25(13) . . . . ? B1 B2 B3 C2 -2.98(12) . . . . ? B5 B2 B3 B6 -40.95(10) . . . . ? B1 B2 B3 B6 -101.18(11) . . . . ? B6 B2 B3 B7 34.41(10) . . . . ? B5 B2 B3 B7 -6.54(13) . . . . ? B1 B2 B3 B7 -66.77(12) . . . . ? C2 C1 B4 B9 1.38(14) . . . . ? B1 C1 B4 B9 -103.08(11) . . . . ? B8 C1 B4 B9 42.12(10) . . . . ? C2 C1 B4 B5 64.86(12) . . . . ? B1 C1 B4 B5 -39.60(10) . . . . ? B8 C1 B4 B5 105.60(10) . . . . ? C2 C1 B4 B8 -40.74(10) . . . . ? B1 C1 B4 B8 -145.20(10) . . . . ? C2 C1 B4 B1 104.46(11) . . . . ? B8 C1 B4 B1 145.20(10) . . . . ? B5 B1 B4 C1 -133.74(11) . . . . ? B2 B1 B4 C1 -99.21(11) . . . . ? C1 B1 B4 B9 94.69(11) . . . . ? B5 B1 B4 B9 -39.05(11) . . . . ? B2 B1 B4 B9 -4.52(14) . . . . ? C1 B1 B4 B5 133.74(11) . . . . ? B2 B1 B4 B5 34.53(10) . . . . ? C1 B1 B4 B8 30.88(10) . . . . ? B5 B1 B4 B8 -102.86(11) . . . . ? B2 B1 B4 B8 -68.33(13) . . . . ? C1 B4 B5 B1 37.19(9) . . . . ? B9 B4 B5 B1 137.37(11) . . . . ? B8 B4 B5 B1 98.64(11) . . . . ? C1 B4 B5 B2 -0.26(14) . . . . ? B9 B4 B5 B2 99.92(12) . . . . ? B8 B4 B5 B2 61.19(14) . . . . ? B1 B4 B5 B2 -37.45(10) . . . . ? C1 B4 B5 B9 -100.17(10) . . . . ? B8 B4 B5 B9 -38.73(10) . . . . ? B1 B4 B5 B9 -137.37(11) . . . . ? C1 B4 B5 B6 -63.36(12) . . . . ? B9 B4 B5 B6 36.82(10) . . . . ? B8 B4 B5 B6 -1.91(14) . . . . ? B1 B4 B5 B6 -100.55(11) . . . . ? C1 B1 B5 B4 -40.05(10) . . . . ? B2 B1 B5 B4 -140.80(11) . . . . ? C1 B1 B5 B2 100.75(11) . . . . ? B4 B1 B5 B2 140.80(11) . . . . ? C1 B1 B5 B9 -2.46(13) . . . . ? B4 B1 B5 B9 37.59(10) . . . . ? B2 B1 B5 B9 -103.21(11) . . . . ? C1 B1 B5 B6 60.22(13) . . . . ? B4 B1 B5 B6 100.27(11) . . . . ? B2 B1 B5 B6 -40.53(10) . . . . ? B6 B2 B5 B4 -96.89(12) . . . . ? B3 B2 B5 B4 -57.42(13) . . . . ? B1 B2 B5 B4 36.82(10) . . . . ? B6 B2 B5 B1 -133.71(11) . . . . ? B3 B2 B5 B1 -94.25(11) . . . . ? B6 B2 B5 B9 -33.23(10) . . . . ? B3 B2 B5 B9 6.23(14) . . . . ? B1 B2 B5 B9 100.48(12) . . . . ? B3 B2 B5 B6 39.47(10) . . . . ? B1 B2 B5 B6 133.71(11) . . . . ? C2 B3 B6 B7 41.98(9) . . . . ? B2 B3 B6 B7 141.72(10) . . . . ? C2 B3 B6 B2 -99.74(10) . . . . ? B7 B3 B6 B2 -141.72(10) . . . . ? C2 B3 B6 B9 3.53(13) . . . . ? B7 B3 B6 B9 -38.45(10) . . . . ? B2 B3 B6 B9 103.27(11) . . . . ? C2 B3 B6 B5 -59.56(12) . . . . ? B7 B3 B6 B5 -101.54(11) . . . . ? B2 B3 B6 B5 40.18(10) . . . . ? B5 B2 B6 B3 134.03(11) . . . . ? B1 B2 B6 B3 94.27(11) . . . . ? B5 B2 B6 B7 97.98(12) . . . . ? B3 B2 B6 B7 -36.05(10) . . . . ? B1 B2 B6 B7 58.22(14) . . . . ? B5 B2 B6 B9 33.49(11) . . . . ? B3 B2 B6 B9 -100.54(12) . . . . ? B1 B2 B6 B9 -6.26(14) . . . . ? B3 B2 B6 B5 -134.03(11) . . . . ? B1 B2 B6 B5 -39.76(10) . . . . ? B4 B5 B6 B3 65.20(13) . . . . ? B1 B5 B6 B3 0.90(14) . . . . ? B2 B5 B6 B3 -41.33(10) . . . . ? B9 B5 B6 B3 101.82(11) . . . . ? B4 B5 B6 B7 0.56(14) . . . . ? B1 B5 B6 B7 -63.74(13) . . . . ? B2 B5 B6 B7 -105.97(12) . . . . ? B9 B5 B6 B7 37.18(10) . . . . ? B4 B5 B6 B2 106.54(12) . . . . ? B1 B5 B6 B2 42.23(10) . . . . ? B9 B5 B6 B2 143.16(11) . . . . ? B4 B5 B6 B9 -36.62(10) . . . . ? B1 B5 B6 B9 -100.92(12) . . . . ? B2 B5 B6 B9 -143.16(11) . . . . ? C1 C2 B7 B6 -67.26(12) . . . . ? B3 C2 B7 B6 40.32(9) . . . . ? B8 C2 B7 B6 -105.41(11) . . . . ? P1 C2 B7 B6 145.00(9) . . . . ? C1 C2 B7 B9 -4.66(13) . . . . ? B3 C2 B7 B9 102.93(11) . . . . ? B8 C2 B7 B9 -42.81(10) . . . . ? P1 C2 B7 B9 -152.39(9) . . . . ? C1 C2 B7 B8 38.15(10) . . . . ? B3 C2 B7 B8 145.73(11) . . . . ? P1 C2 B7 B8 -109.59(11) . . . . ? C1 C2 B7 B3 -107.59(11) . . . . ? B8 C2 B7 B3 -145.73(11) . . . . ? P1 C2 B7 B3 104.68(11) . . . . ? B3 B6 B7 C2 -38.12(8) . . . . ? B2 B6 B7 C2 -1.96(13) . . . . ? B9 B6 B7 C2 98.73(10) . . . . ? B5 B6 B7 C2 61.46(12) . . . . ? B3 B6 B7 B9 -136.85(10) . . . . ? B2 B6 B7 B9 -100.70(12) . . . . ? B5 B6 B7 B9 -37.27(10) . . . . ? B3 B6 B7 B8 -98.61(11) . . . . ? B2 B6 B7 B8 -62.46(13) . . . . ? B9 B6 B7 B8 38.24(10) . . . . ? B5 B6 B7 B8 0.97(14) . . . . ? B2 B6 B7 B3 36.15(10) . . . . ? B9 B6 B7 B3 136.85(10) . . . . ? B5 B6 B7 B3 99.58(11) . . . . ? B6 B3 B7 C2 132.07(10) . . . . ? B2 B3 B7 C2 97.47(11) . . . . ? C2 B3 B7 B6 -132.07(10) . . . . ? B2 B3 B7 B6 -34.60(10) . . . . ? C2 B3 B7 B9 -93.06(11) . . . . ? B6 B3 B7 B9 39.00(10) . . . . ? B2 B3 B7 B9 4.41(13) . . . . ? C2 B3 B7 B8 -30.21(10) . . . . ? B6 B3 B7 B8 101.86(11) . . . . ? B2 B3 B7 B8 67.26(13) . . . . ? B1 C1 B8 C2 -101.46(12) . . . . ? B4 C1 B8 C2 -137.27(11) . . . . ? C2 C1 B8 B4 137.27(11) . . . . ? B1 C1 B8 B4 35.81(11) . . . . ? C2 C1 B8 B9 95.82(10) . . . . ? B1 C1 B8 B9 -5.65(14) . . . . ? B4 C1 B8 B9 -41.45(9) . . . . ? C2 C1 B8 B7 34.34(10) . . . . ? B1 C1 B8 B7 -67.12(13) . . . . ? B4 C1 B8 B7 -102.93(11) . . . . ? B3 C2 B8 C1 105.35(12) . . . . ? B7 C2 B8 C1 140.14(11) . . . . ? P1 C2 B8 C1 -106.25(10) . . . . ? C1 C2 B8 B4 -36.29(9) . . . . ? B3 C2 B8 B4 69.06(13) . . . . ? B7 C2 B8 B4 103.86(11) . . . . ? P1 C2 B8 B4 -142.54(9) . . . . ? C1 C2 B8 B9 -97.42(11) . . . . ? B3 C2 B8 B9 7.92(14) . . . . ? B7 C2 B8 B9 42.72(9) . . . . ? P1 C2 B8 B9 156.33(9) . . . . ? C1 C2 B8 B7 -140.14(11) . . . . ? B3 C2 B8 B7 -34.80(11) . . . . ? P1 C2 B8 B7 113.61(10) . . . . ? B9 B4 B8 C1 -131.69(10) . . . . ? B5 B4 B8 C1 -92.40(11) . . . . ? B1 B4 B8 C1 -29.24(9) . . . . ? C1 B4 B8 C2 34.04(8) . . . . ? B9 B4 B8 C2 -97.65(10) . . . . ? B5 B4 B8 C2 -58.36(12) . . . . ? B1 B4 B8 C2 4.79(13) . . . . ? C1 B4 B8 B9 131.69(10) . . . . ? B5 B4 B8 B9 39.30(10) . . . . ? B1 B4 B8 B9 102.45(11) . . . . ? C1 B4 B8 B7 94.92(10) . . . . ? B9 B4 B8 B7 -36.77(10) . . . . ? B5 B4 B8 B7 2.52(14) . . . . ? B1 B4 B8 B7 65.67(13) . . . . ? C2 B7 B8 C1 -32.13(9) . . . . ? B6 B7 B8 C1 58.81(13) . . . . ? B9 B7 B8 C1 97.72(11) . . . . ? B3 B7 B8 C1 -3.41(13) . . . . ? B6 B7 B8 C2 90.95(11) . . . . ? B9 B7 B8 C2 129.86(10) . . . . ? B3 B7 B8 C2 28.73(9) . . . . ? C2 B7 B8 B4 -93.09(11) . . . . ? B6 B7 B8 B4 -2.15(14) . . . . ? B9 B7 B8 B4 36.77(10) . . . . ? B3 B7 B8 B4 -64.36(13) . . . . ? C2 B7 B8 B9 -129.86(10) . . . . ? B6 B7 B8 B9 -38.91(10) . . . . ? B3 B7 B8 B9 -101.13(11) . . . . ? C1 B4 B9 B7 -4.26(14) . . . . ? B5 B4 B9 B7 -99.91(11) . . . . ? B8 B4 B9 B7 37.32(10) . . . . ? B1 B4 B9 B7 -61.73(14) . . . . ? C1 B4 B9 B8 -41.58(9) . . . . ? B5 B4 B9 B8 -137.24(11) . . . . ? B1 B4 B9 B8 -99.06(11) . . . . ? C1 B4 B9 B6 58.14(13) . . . . ? B5 B4 B9 B6 -37.51(10) . . . . ? B8 B4 B9 B6 99.73(11) . . . . ? B1 B4 B9 B6 0.67(14) . . . . ? C1 B4 B9 B5 95.65(11) . . . . ? B8 B4 B9 B5 137.24(11) . . . . ? B1 B4 B9 B5 38.18(10) . . . . ? C2 B7 B9 B4 5.30(13) . . . . ? B6 B7 B9 B4 100.14(11) . . . . ? B8 B7 B9 B4 -37.04(10) . . . . ? B3 B7 B9 B4 62.13(13) . . . . ? C2 B7 B9 B8 42.35(9) . . . . ? B6 B7 B9 B8 137.18(11) . . . . ? B3 B7 B9 B8 99.18(11) . . . . ? C2 B7 B9 B6 -94.83(10) . . . . ? B8 B7 B9 B6 -137.18(11) . . . . ? B3 B7 B9 B6 -38.00(10) . . . . ? C2 B7 B9 B5 -57.31(12) . . . . ? B6 B7 B9 B5 37.53(10) . . . . ? B8 B7 B9 B5 -99.65(11) . . . . ? B3 B7 B9 B5 -0.48(14) . . . . ? C1 B8 B9 B4 40.94(9) . . . . ? C2 B8 B9 B4 96.33(10) . . . . ? B7 B8 B9 B4 138.66(10) . . . . ? C1 B8 B9 B7 -97.72(10) . . . . ? C2 B8 B9 B7 -42.34(9) . . . . ? B4 B8 B9 B7 -138.66(10) . . . . ? C1 B8 B9 B6 -60.19(12) . . . . ? C2 B8 B9 B6 -4.81(13) . . . . ? B4 B8 B9 B6 -101.13(11) . . . . ? B7 B8 B9 B6 37.53(10) . . . . ? C1 B8 B9 B5 3.42(12) . . . . ? C2 B8 B9 B5 58.80(12) . . . . ? B4 B8 B9 B5 -37.52(10) . . . . ? B7 B8 B9 B5 101.14(11) . . . . ? B3 B6 B9 B4 -62.06(14) . . . . ? B7 B6 B9 B4 -101.29(12) . . . . ? B2 B6 B9 B4 3.64(15) . . . . ? B5 B6 B9 B4 36.91(10) . . . . ? B3 B6 B9 B7 39.23(10) . . . . ? B2 B6 B9 B7 104.93(12) . . . . ? B5 B6 B9 B7 138.20(11) . . . . ? B3 B6 B9 B8 1.01(14) . . . . ? B7 B6 B9 B8 -38.23(10) . . . . ? B2 B6 B9 B8 66.71(13) . . . . ? B5 B6 B9 B8 99.97(11) . . . . ? B3 B6 B9 B5 -98.97(11) . . . . ? B7 B6 B9 B5 -138.20(11) . . . . ? B2 B6 B9 B5 -33.26(11) . . . . ? B1 B5 B9 B4 -38.55(10) . . . . ? B2 B5 B9 B4 -105.16(12) . . . . ? B6 B5 B9 B4 -138.29(11) . . . . ? B4 B5 B9 B7 101.47(12) . . . . ? B1 B5 B9 B7 62.92(13) . . . . ? B2 B5 B9 B7 -3.69(14) . . . . ? B6 B5 B9 B7 -36.82(10) . . . . ? B4 B5 B9 B8 37.82(10) . . . . ? B1 B5 B9 B8 -0.73(13) . . . . ? B2 B5 B9 B8 -67.33(13) . . . . ? B6 B5 B9 B8 -100.47(11) . . . . ? B4 B5 B9 B6 138.29(11) . . . . ? B1 B5 B9 B6 99.74(11) . . . . ? B2 B5 B9 B6 33.13(10) . . . . ? C1 C2 P1 C3 -165.22(9) . . . . ? B3 C2 P1 C3 56.09(10) . . . . ? B8 C2 P1 C3 -92.89(10) . . . . ? B7 C2 P1 C3 -18.57(11) . . . . ? C1 C2 P1 C4 -44.41(11) . . . . ? B3 C2 P1 C4 176.90(9) . . . . ? B8 C2 P1 C4 27.93(11) . . . . ? B7 C2 P1 C4 102.24(10) . . . . ? C1 C2 P1 C10 76.39(10) . . . . ? B3 C2 P1 C10 -62.30(10) . . . . ? B8 C2 P1 C10 148.73(9) . . . . ? B7 C2 P1 C10 -136.96(9) . . . . ? C5 C4 P1 C2 90.51(12) . . . . ? C9 C4 P1 C2 -89.13(12) . . . . ? C5 C4 P1 C3 -147.80(12) . . . . ? C9 C4 P1 C3 32.55(13) . . . . ? C5 C4 P1 C10 -28.61(13) . . . . ? C9 C4 P1 C10 151.74(11) . . . . ? C15 C10 P1 C2 139.56(11) . . . . ? C11 C10 P1 C2 -41.06(12) . . . . ? C15 C10 P1 C3 20.85(13) . . . . ? C11 C10 P1 C3 -159.77(11) . . . . ? C15 C10 P1 C4 -97.70(11) . . . . ? C11 C10 P1 C4 81.69(12) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 30.64 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.499 _refine_diff_density_min -0.584 _refine_diff_density_rms 0.072