Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_afx08a _database_code_CSD 186128 data_global _journal_coden_Cambridge 186 loop_ _publ_author_name _publ_author_address 'Andreas Franken' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Daniel L. Ormsby' ; Accelrys Inc., 9685 Scranton Road, San Diego, CA 92121-3752, USA ; 'Colin A. Kilner' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'William Clegg' ; Department of Chemistry of the University of Newcastle, Newcastle upon Tyne, UK NE1 7RU, Northern England, EU. ; 'J. D. Kennedy' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Mark Thornton-Pett' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; _publ_contact_author_name 'Prof John D Kennedy' _publ_contact_author_address ; The School of Chemistry University of Leeds Leeds LS2 9JT UNITED KINGDOM ; _publ_contact_author_email JOHNK@CHEM.LEEDS.AC.UK _publ_requested_journal 'J. Chem. Soc., Dalton Trans.' _publ_contact_letter ; The following X sets of data are supplementary data for the the crystal structures included in the paper, details of which are given below ; #======================================================================= # 2. TITLE AND AUTHOR LIST _publ_section_title ; Monocarbaborane anion chemistry. The substantiation of the C-arylated [PhCB6H6]- seven-vertex closo cluster anion by singe-crystal synchrotron X-ray diffraction analysis ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; [NEt4]+[2-Ph-closo-2-CB6H6]- ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H31 B6 N' _chemical_formula_weight 290.27 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 14.438(3) _cell_length_b 15.762(3) _cell_length_c 16.877(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3840.6(14) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.004 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9845 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6883 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker AXS SMART 1K CCD diffractometer' _diffrn_measurement_method 'omega rotation with narrow frames' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10306 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4073 _reflns_number_gt 3385 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.1099P)^2^+1.1144P] 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 4073 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0807 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1792 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 C2 C 0.15835(11) 0.02098(10) 0.60613(8) 0.0209(3) Uani 1 1 d . . . C12 C 0.51708(13) 0.26695(11) 0.33658(11) 0.0301(4) Uani 1 1 d . . . H12A H 0.5022(15) 0.3039(14) 0.2938(13) 0.039(6) Uiso 1 1 d . . . H12B H 0.5250(14) 0.2988(13) 0.3837(12) 0.031(5) Uiso 1 1 d . . . C13 C 0.59863(16) 0.21095(16) 0.31663(18) 0.0513(6) Uani 1 1 d . . . H13A H 0.608(2) 0.175(2) 0.3596(19) 0.078(10) Uiso 1 1 d . . . H13B H 0.6536(19) 0.249(2) 0.3084(17) 0.066(8) Uiso 1 1 d . . . H13C H 0.583(2) 0.172(2) 0.2651(18) 0.074(9) Uiso 1 1 d . . . C14 C 0.43822(14) 0.15865(11) 0.42116(10) 0.0302(4) Uani 1 1 d . . . H14A H 0.3781(16) 0.1351(14) 0.4254(12) 0.036(5) Uiso 1 1 d . . . H14B H 0.4813(14) 0.1181(14) 0.4003(12) 0.030(5) Uiso 1 1 d . . . C15 C 0.46862(18) 0.19851(15) 0.49834(11) 0.0416(5) Uani 1 1 d . . . H15A H 0.5248(18) 0.2229(15) 0.4971(14) 0.043(7) Uiso 1 1 d . . . H15B H 0.4685(19) 0.1519(19) 0.5388(17) 0.066(8) Uiso 1 1 d . . . H15C H 0.4231(19) 0.241(2) 0.5156(16) 0.058(7) Uiso 1 1 d . . . C16 C 0.39797(15) 0.16747(11) 0.28129(10) 0.0330(4) Uani 1 1 d . . . H16A H 0.3371(16) 0.1422(15) 0.2965(13) 0.040(6) Uiso 1 1 d . . . H16B H 0.4446(15) 0.1276(14) 0.2755(12) 0.035(5) Uiso 1 1 d . . . C17 C 0.3876(2) 0.21671(15) 0.20444(12) 0.0499(6) Uani 1 1 d . . . H17A H 0.3472(19) 0.266(2) 0.2116(16) 0.063(8) Uiso 1 1 d . . . H17B H 0.367(2) 0.176(2) 0.1670(19) 0.085(10) Uiso 1 1 d . . . H17C H 0.4498(17) 0.2331(16) 0.1900(15) 0.045(7) Uiso 1 1 d . . . C18 C 0.35538(14) 0.28811(11) 0.37037(11) 0.0320(4) Uani 1 1 d . . . H18A H 0.3884(17) 0.3216(16) 0.4152(14) 0.048(6) Uiso 1 1 d . . . H18B H 0.3530(15) 0.3230(15) 0.3249(13) 0.036(5) Uiso 1 1 d . . . C19 C 0.26084(16) 0.25765(18) 0.39288(16) 0.0498(6) Uani 1 1 d . . . H19A H 0.2341(15) 0.2274(14) 0.3484(14) 0.036(6) Uiso 1 1 d . . . H19B H 0.225(2) 0.3096(19) 0.4006(16) 0.067(8) Uiso 1 1 d . . . H19C H 0.263(2) 0.226(2) 0.446(2) 0.096(11) Uiso 1 1 d . . . C21 C 0.09473(11) 0.02979(9) 0.67529(8) 0.0196(3) Uani 1 1 d . . . C22 C 0.12842(11) 0.05575(10) 0.74923(9) 0.0232(4) Uani 1 1 d . . . H22 H 0.1965(14) 0.0648(12) 0.7556(10) 0.023(4) Uiso 1 1 d . . . C23 C 0.06958(13) 0.06305(11) 0.81394(9) 0.0272(4) Uani 1 1 d . . . H23 H 0.0946(15) 0.0806(15) 0.8637(13) 0.037(6) Uiso 1 1 d . . . C24 C -0.02428(13) 0.04341(11) 0.80563(10) 0.0288(4) Uani 1 1 d . . . H24 H -0.0664(14) 0.0466(13) 0.8504(12) 0.027(5) Uiso 1 1 d . . . C25 C -0.05809(12) 0.01713(11) 0.73229(10) 0.0271(4) Uani 1 1 d . . . H25 H -0.1217(14) 0.0044(12) 0.7270(10) 0.021(4) Uiso 1 1 d . . . C26 C 0.00113(12) 0.01062(10) 0.66746(9) 0.0233(4) Uani 1 1 d . . . H26 H -0.0216(13) -0.0029(13) 0.6133(12) 0.026(5) Uiso 1 1 d . . . B1 B 0.25082(14) 0.07425(13) 0.56197(11) 0.0298(4) Uani 1 1 d . . . H1 H 0.2806(15) 0.1363(14) 0.5844(13) 0.040(6) Uiso 1 1 d . . . B3 B 0.13520(14) 0.05558(13) 0.52191(10) 0.0275(4) Uani 1 1 d . . . H3 H 0.0697(14) 0.0914(13) 0.5101(12) 0.032(5) Uiso 1 1 d . . . B4 B 0.22398(15) 0.02719(14) 0.46693(11) 0.0328(5) Uani 1 1 d . . . H4 H 0.2320(15) 0.0427(14) 0.4045(13) 0.040(6) Uiso 1 1 d . . . B5 B 0.29847(16) -0.02328(15) 0.52491(12) 0.0357(5) Uani 1 1 d . . . H5 H 0.367(2) -0.0460(18) 0.5062(16) 0.067(8) Uiso 1 1 d . . . B6 B 0.25238(14) -0.02637(13) 0.61428(11) 0.0289(4) Uani 1 1 d . . . H6 H 0.2738(16) -0.0535(15) 0.6749(14) 0.046(6) Uiso 1 1 d . . . B7 B 0.17743(15) -0.05260(13) 0.53133(11) 0.0297(4) Uani 1 1 d . . . H7 H 0.1354(18) -0.1098(17) 0.5251(15) 0.058(7) Uiso 1 1 d . . . N1 N 0.42683(10) 0.22026(8) 0.35243(7) 0.0227(3) 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 C2 0.0229(8) 0.0251(8) 0.0148(7) -0.0020(5) -0.0013(6) -0.0032(6) C12 0.0340(10) 0.0252(8) 0.0311(9) 0.0045(7) -0.0005(7) -0.0044(7) C13 0.0381(12) 0.0452(13) 0.0706(16) 0.0118(12) 0.0145(11) 0.0010(10) C14 0.0401(10) 0.0265(9) 0.0239(8) 0.0084(6) 0.0024(7) 0.0019(7) C15 0.0552(14) 0.0478(12) 0.0219(9) 0.0075(8) -0.0032(8) 0.0047(10) C16 0.0497(12) 0.0259(9) 0.0234(8) -0.0054(6) -0.0029(8) -0.0041(8) C17 0.0825(19) 0.0440(13) 0.0232(9) -0.0027(8) -0.0113(10) -0.0099(12) C18 0.0406(11) 0.0278(9) 0.0277(8) 0.0024(7) 0.0033(7) 0.0093(7) C19 0.0396(12) 0.0557(14) 0.0541(14) 0.0094(11) 0.0090(10) 0.0129(10) C21 0.0253(8) 0.0184(7) 0.0152(7) 0.0006(5) -0.0006(6) 0.0016(6) C22 0.0250(9) 0.0259(8) 0.0187(7) -0.0007(6) -0.0022(6) 0.0002(6) C23 0.0389(10) 0.0273(8) 0.0155(7) -0.0033(6) -0.0005(6) 0.0005(7) C24 0.0332(10) 0.0289(9) 0.0242(8) 0.0012(6) 0.0077(7) 0.0028(7) C25 0.0249(9) 0.0271(8) 0.0292(9) 0.0014(6) 0.0031(7) 0.0003(6) C26 0.0267(8) 0.0244(8) 0.0188(7) 0.0009(6) -0.0019(6) 0.0003(6) B1 0.0297(10) 0.0381(11) 0.0218(8) -0.0002(7) 0.0009(7) -0.0104(8) B3 0.0318(10) 0.0347(10) 0.0161(8) 0.0021(7) -0.0034(7) -0.0007(8) B4 0.0355(11) 0.0449(12) 0.0181(8) -0.0007(7) 0.0023(7) -0.0074(9) B5 0.0319(11) 0.0502(13) 0.0250(9) -0.0048(8) 0.0043(8) 0.0053(9) B6 0.0252(10) 0.0403(11) 0.0213(8) 0.0002(7) -0.0004(7) 0.0039(8) B7 0.0367(11) 0.0325(10) 0.0199(8) -0.0073(7) 0.0022(7) -0.0029(8) N1 0.0326(8) 0.0194(7) 0.0160(6) 0.0008(5) 0.0000(5) -0.0002(5) _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 C2 C21 1.492(2) . ? C2 B6 1.555(2) . ? C2 B3 1.559(2) . ? C2 B7 1.736(2) . ? C2 B1 1.744(2) . ? C12 C13 1.510(3) . ? C12 N1 1.520(2) . ? C14 C15 1.511(3) . ? C14 N1 1.522(2) . ? C16 C17 1.519(3) . ? C16 N1 1.519(2) . ? C18 C19 1.496(3) . ? C18 N1 1.516(2) . ? C21 C26 1.391(2) . ? C21 C22 1.400(2) . ? C22 C23 1.388(2) . ? C23 C24 1.397(3) . ? C24 C25 1.393(2) . ? C25 C26 1.392(2) . ? B1 B5 1.796(3) . ? B1 B4 1.809(3) . ? B1 B6 1.815(3) . ? B1 B3 1.825(3) . ? B3 B4 1.645(3) . ? B3 B7 1.818(3) . ? B4 B5 1.657(3) . ? B4 B7 1.793(3) . ? B5 B6 1.649(3) . ? B5 B7 1.811(3) . ? B6 B7 1.817(3) . ? 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 C21 C2 B6 120.86(13) . . ? C21 C2 B3 123.29(14) . . ? B6 C2 B3 115.83(14) . . ? C21 C2 B7 136.78(13) . . ? B6 C2 B7 66.75(12) . . ? B3 C2 B7 66.71(11) . . ? C21 C2 B1 139.53(13) . . ? B6 C2 B1 66.46(12) . . ? B3 C2 B1 66.81(12) . . ? B7 C2 B1 83.65(11) . . ? C13 C12 N1 115.13(16) . . ? C15 C14 N1 115.03(15) . . ? C17 C16 N1 114.98(15) . . ? C19 C18 N1 116.43(16) . . ? C26 C21 C22 119.05(14) . . ? C26 C21 C2 120.24(13) . . ? C22 C21 C2 120.70(14) . . ? C23 C22 C21 120.83(15) . . ? C22 C23 C24 119.74(15) . . ? C25 C24 C23 119.66(15) . . ? C26 C25 C24 120.32(16) . . ? C21 C26 C25 120.39(15) . . ? C2 B1 B5 91.72(13) . . ? C2 B1 B4 91.01(12) . . ? B5 B1 B4 54.73(12) . . ? C2 B1 B6 51.77(10) . . ? B5 B1 B6 54.34(11) . . ? B4 B1 B6 94.34(13) . . ? C2 B1 B3 51.73(9) . . ? B5 B1 B3 94.78(13) . . ? B4 B1 B3 53.81(11) . . ? B6 B1 B3 92.90(13) . . ? C2 B3 B4 104.60(15) . . ? C2 B3 B7 61.32(10) . . ? B4 B3 B7 62.14(12) . . ? C2 B3 B1 61.47(11) . . ? B4 B3 B1 62.61(12) . . ? B7 B3 B1 79.16(12) . . ? B3 B4 B5 107.65(14) . . ? B3 B4 B7 63.68(12) . . ? B5 B4 B7 63.17(13) . . ? B3 B4 B1 63.59(12) . . ? B5 B4 B1 62.24(12) . . ? B7 B4 B1 80.24(12) . . ? B6 B5 B4 107.00(15) . . ? B6 B5 B1 63.41(12) . . ? B4 B5 B1 63.03(12) . . ? B6 B5 B7 63.16(12) . . ? B4 B5 B7 62.07(13) . . ? B1 B5 B7 80.10(13) . . ? C2 B6 B5 104.91(14) . . ? C2 B6 B1 61.77(11) . . ? B5 B6 B1 62.26(12) . . ? C2 B6 B7 61.40(11) . . ? B5 B6 B7 62.77(12) . . ? B1 B6 B7 79.44(12) . . ? C2 B7 B4 91.82(13) . . ? C2 B7 B5 91.49(12) . . ? B4 B7 B5 54.76(12) . . ? C2 B7 B6 51.85(9) . . ? B4 B7 B6 94.83(13) . . ? B5 B7 B6 54.08(11) . . ? C2 B7 B3 51.97(9) . . ? B4 B7 B3 54.18(11) . . ? B5 B7 B3 94.54(14) . . ? B6 B7 B3 93.08(12) . . ? C18 N1 C16 110.94(14) . . ? C18 N1 C12 106.07(13) . . ? C16 N1 C12 111.17(13) . . ? C18 N1 C14 111.80(13) . . ? C16 N1 C14 106.42(13) . . ? C12 N1 C14 110.52(13) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.494 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.085