# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Fontaine, Frederic-Georges' _publ_contact_author_email frederic.fontaine@chm.ulaval.ca _publ_section_title ; Synthesis of a 1-boratabenzene-(2,3,4,5-tetramethylphosphole): towards a planar monophosphole ; loop_ _publ_author_name F.-G.Fontaine L.Maron G.Bolanger-Chabot P.Rioux data_frede1_0m _database_code_depnum_ccdc_archive 'CCDC 780138' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H34 B2 Fe P2' _chemical_formula_weight 485.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe -1.1336 3.1974 '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 7.0954(2) _cell_length_b 13.2891(3) _cell_length_c 13.6815(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.0610(10) _cell_angle_gamma 90.00 _cell_volume 1256.68(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3184 _cell_measurement_theta_min 4.70 _cell_measurement_theta_max 70.92 _exptl_crystal_description ? _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 6.080 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.3760 _exptl_absorpt_correction_T_max 0.6419 _exptl_absorpt_process_details 'XPREP (Bruker, 2005a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX II CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16308 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.70 _diffrn_reflns_theta_max 72.51 _reflns_number_total 2481 _reflns_number_gt 2033 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 (Bruker, 2005b)' _computing_cell_refinement 'APEX 2 (Bruker, 2005b)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.0526P)^2^+0.4026P] 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 2481 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Fe1 Fe 0.0000 1.0000 0.0000 0.02504(15) Uani 1 2 d S . . B1 B -0.1164(4) 0.9393(2) 0.1265(2) 0.0317(6) Uani 1 1 d . . . C1 C -0.2623(3) 0.94189(19) 0.02755(18) 0.0330(5) Uani 1 1 d . . . H1 H -0.3117 0.8780 -0.0038 0.040 Uiso 1 1 calc R . . C2 C -0.2955(3) 1.0306(2) -0.0308(2) 0.0365(6) Uani 1 1 d . . . H2 H -0.3693 1.0255 -0.1004 0.044 Uiso 1 1 calc R . . C3 C -0.1889(4) 1.11953(18) -0.00049(19) 0.0359(6) Uani 1 1 d . . . H3 H -0.1929 1.1739 -0.0493 0.043 Uiso 1 1 calc R . . C4 C -0.0450(4) 1.12164(18) 0.09007(19) 0.0369(6) Uani 1 1 d . . . H4 H 0.0489 1.1769 0.1007 0.044 Uiso 1 1 calc R . . C5 C -0.0040(4) 1.03569(19) 0.15188(18) 0.0344(5) Uani 1 1 d . . . H5 H 0.1182 1.0336 0.2025 0.041 Uiso 1 1 calc R . . P1 P -0.06940(10) 0.82040(5) 0.21102(5) 0.03616(18) Uani 1 1 d . . . C6 C 0.1844(4) 0.81044(19) 0.26670(18) 0.0367(6) Uani 1 1 d . . . C7 C 0.2546(4) 0.72392(19) 0.23649(18) 0.0364(6) Uani 1 1 d . . . C8 C 0.1158(4) 0.66848(18) 0.16052(18) 0.0371(6) Uani 1 1 d . . . C9 C -0.0614(4) 0.71209(19) 0.13329(18) 0.0381(6) Uani 1 1 d . . . C10 C 0.2918(5) 0.8805(2) 0.3467(2) 0.0549(8) Uani 1 1 d . . . H10A H 0.3418 0.8432 0.4070 0.082 Uiso 1 1 calc R . . H10B H 0.2052 0.9317 0.3597 0.082 Uiso 1 1 calc R . . H10C H 0.3968 0.9114 0.3242 0.082 Uiso 1 1 calc R . . C11 C 0.4533(4) 0.6828(2) 0.2797(2) 0.0497(7) Uani 1 1 d . . . H11A H 0.5285 0.7323 0.3227 0.075 Uiso 1 1 calc R . . H11B H 0.5154 0.6666 0.2262 0.075 Uiso 1 1 calc R . . H11C H 0.4429 0.6232 0.3178 0.075 Uiso 1 1 calc R . . C12 C 0.1708(5) 0.5708(2) 0.1189(2) 0.0514(7) Uani 1 1 d . . . H12A H 0.0621 0.5449 0.0704 0.077 Uiso 1 1 calc R . . H12B H 0.2087 0.5230 0.1724 0.077 Uiso 1 1 calc R . . H12C H 0.2768 0.5820 0.0872 0.077 Uiso 1 1 calc R . . C13 C -0.2338(5) 0.6732(2) 0.0567(2) 0.0536(8) Uani 1 1 d . . . H13A H -0.2096 0.6795 -0.0092 0.080 Uiso 1 1 calc R . . H13B H -0.3464 0.7116 0.0606 0.080 Uiso 1 1 calc R . . H13C H -0.2549 0.6037 0.0702 0.080 Uiso 1 1 calc R . . 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 Fe1 0.0256(3) 0.0256(2) 0.0251(2) -0.0011(2) 0.00816(18) 0.0008(2) B1 0.0344(15) 0.0331(14) 0.0321(14) 0.0037(11) 0.0167(11) 0.0035(11) C1 0.0262(12) 0.0378(13) 0.0369(13) 0.0048(10) 0.0113(10) -0.0008(10) C2 0.0264(13) 0.0453(14) 0.0397(13) 0.0088(11) 0.0119(10) 0.0073(10) C3 0.0379(14) 0.0329(13) 0.0426(14) 0.0058(10) 0.0214(11) 0.0117(10) C4 0.0467(16) 0.0283(12) 0.0410(14) -0.0076(10) 0.0210(12) -0.0001(10) C5 0.0406(14) 0.0392(13) 0.0258(11) -0.0058(10) 0.0126(10) 0.0042(11) P1 0.0398(4) 0.0373(3) 0.0315(3) 0.0067(3) 0.0083(3) -0.0004(3) C6 0.0415(15) 0.0396(13) 0.0266(12) 0.0037(10) 0.0028(10) -0.0018(11) C7 0.0403(15) 0.0389(13) 0.0300(12) 0.0066(10) 0.0083(10) -0.0017(11) C8 0.0495(16) 0.0321(13) 0.0302(12) 0.0062(10) 0.0101(11) -0.0027(11) C9 0.0468(16) 0.0341(13) 0.0318(12) 0.0048(10) 0.0051(11) -0.0086(11) C10 0.064(2) 0.0517(17) 0.0403(15) -0.0064(13) -0.0067(14) 0.0003(15) C11 0.0464(17) 0.0537(17) 0.0473(16) 0.0074(13) 0.0072(13) 0.0070(13) C12 0.071(2) 0.0400(15) 0.0436(16) 0.0007(12) 0.0140(15) 0.0008(13) C13 0.0575(19) 0.0416(16) 0.0532(17) 0.0054(13) -0.0058(14) -0.0136(13) _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 Fe1 C3 2.077(2) . ? Fe1 C3 2.077(2) 3_575 ? Fe1 C2 2.083(2) 3_575 ? Fe1 C2 2.083(2) . ? Fe1 C4 2.100(2) 3_575 ? Fe1 C4 2.100(2) . ? Fe1 C1 2.126(2) 3_575 ? Fe1 C1 2.126(2) . ? Fe1 C5 2.138(2) 3_575 ? Fe1 C5 2.138(2) . ? Fe1 B1 2.230(3) 3_575 ? Fe1 B1 2.230(3) . ? B1 C1 1.507(4) . ? B1 C5 1.508(4) . ? B1 P1 1.942(3) . ? C1 C2 1.413(3) . ? C1 H1 0.9800 . ? C2 C3 1.415(4) . ? C2 H2 0.9800 . ? C3 C4 1.416(4) . ? C3 H3 0.9800 . ? C4 C5 1.412(4) . ? C4 H4 0.9800 . ? C5 H5 0.9800 . ? P1 C6 1.795(3) . ? P1 C9 1.798(3) . ? C6 C7 1.354(4) . ? C6 C10 1.506(4) . ? C7 C8 1.460(3) . ? C7 C11 1.503(4) . ? C8 C9 1.358(4) . ? C8 C12 1.505(4) . ? C9 C13 1.510(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 C3 Fe1 C3 180.0 . 3_575 ? C3 Fe1 C2 140.25(10) . 3_575 ? C3 Fe1 C2 39.76(10) 3_575 3_575 ? C3 Fe1 C2 39.75(10) . . ? C3 Fe1 C2 140.25(10) 3_575 . ? C2 Fe1 C2 179.999(1) 3_575 . ? C3 Fe1 C4 140.36(10) . 3_575 ? C3 Fe1 C4 39.64(10) 3_575 3_575 ? C2 Fe1 C4 71.89(11) 3_575 3_575 ? C2 Fe1 C4 108.11(11) . 3_575 ? C3 Fe1 C4 39.64(10) . . ? C3 Fe1 C4 140.36(10) 3_575 . ? C2 Fe1 C4 108.11(11) 3_575 . ? C2 Fe1 C4 71.89(11) . . ? C4 Fe1 C4 179.999(1) 3_575 . ? C3 Fe1 C1 108.15(9) . 3_575 ? C3 Fe1 C1 71.85(9) 3_575 3_575 ? C2 Fe1 C1 39.20(9) 3_575 3_575 ? C2 Fe1 C1 140.80(9) . 3_575 ? C4 Fe1 C1 85.43(10) 3_575 3_575 ? C4 Fe1 C1 94.56(10) . 3_575 ? C3 Fe1 C1 71.85(9) . . ? C3 Fe1 C1 108.15(9) 3_575 . ? C2 Fe1 C1 140.80(9) 3_575 . ? C2 Fe1 C1 39.21(9) . . ? C4 Fe1 C1 94.57(10) 3_575 . ? C4 Fe1 C1 85.43(10) . . ? C1 Fe1 C1 180.00(5) 3_575 . ? C3 Fe1 C5 108.47(10) . 3_575 ? C3 Fe1 C5 71.53(10) 3_575 3_575 ? C2 Fe1 C5 85.38(10) 3_575 3_575 ? C2 Fe1 C5 94.62(10) . 3_575 ? C4 Fe1 C5 38.90(10) 3_575 3_575 ? C4 Fe1 C5 141.10(10) . 3_575 ? C1 Fe1 C5 72.78(10) 3_575 3_575 ? C1 Fe1 C5 107.22(10) . 3_575 ? C3 Fe1 C5 71.53(10) . . ? C3 Fe1 C5 108.47(10) 3_575 . ? C2 Fe1 C5 94.62(10) 3_575 . ? C2 Fe1 C5 85.38(10) . . ? C4 Fe1 C5 141.10(10) 3_575 . ? C4 Fe1 C5 38.90(10) . . ? C1 Fe1 C5 107.22(10) 3_575 . ? C1 Fe1 C5 72.78(10) . . ? C5 Fe1 C5 180.00(14) 3_575 . ? C3 Fe1 B1 94.17(10) . 3_575 ? C3 Fe1 B1 85.83(10) 3_575 3_575 ? C2 Fe1 B1 72.24(10) 3_575 3_575 ? C2 Fe1 B1 107.76(10) . 3_575 ? C4 Fe1 B1 72.00(10) 3_575 3_575 ? C4 Fe1 B1 108.00(10) . 3_575 ? C1 Fe1 B1 40.40(10) 3_575 3_575 ? C1 Fe1 B1 139.60(10) . 3_575 ? C5 Fe1 B1 40.31(10) 3_575 3_575 ? C5 Fe1 B1 139.69(10) . 3_575 ? C3 Fe1 B1 85.83(10) . . ? C3 Fe1 B1 94.17(10) 3_575 . ? C2 Fe1 B1 107.76(10) 3_575 . ? C2 Fe1 B1 72.24(10) . . ? C4 Fe1 B1 108.00(10) 3_575 . ? C4 Fe1 B1 72.00(10) . . ? C1 Fe1 B1 139.60(10) 3_575 . ? C1 Fe1 B1 40.40(10) . . ? C5 Fe1 B1 139.69(10) 3_575 . ? C5 Fe1 B1 40.31(10) . . ? B1 Fe1 B1 180.0 3_575 . ? C1 B1 C5 114.1(2) . . ? C1 B1 P1 122.97(19) . . ? C5 B1 P1 122.9(2) . . ? C1 B1 Fe1 66.07(13) . . ? C5 B1 Fe1 66.54(13) . . ? P1 B1 Fe1 135.44(14) . . ? C2 C1 B1 121.3(2) . . ? C2 C1 Fe1 68.77(13) . . ? B1 C1 Fe1 73.54(14) . . ? C2 C1 H1 118.6 . . ? B1 C1 H1 118.6 . . ? Fe1 C1 H1 118.6 . . ? C1 C2 C3 121.5(2) . . ? C1 C2 Fe1 72.02(13) . . ? C3 C2 Fe1 69.90(14) . . ? C1 C2 H2 118.4 . . ? C3 C2 H2 118.4 . . ? Fe1 C2 H2 118.4 . . ? C2 C3 C4 120.3(2) . . ? C2 C3 Fe1 70.35(14) . . ? C4 C3 Fe1 71.06(14) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? Fe1 C3 H3 119.1 . . ? C5 C4 C3 121.2(2) . . ? C5 C4 Fe1 71.98(13) . . ? C3 C4 Fe1 69.31(13) . . ? C5 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? Fe1 C4 H4 118.4 . . ? C4 C5 B1 121.5(2) . . ? C4 C5 Fe1 69.11(13) . . ? B1 C5 Fe1 73.15(13) . . ? C4 C5 H5 118.4 . . ? B1 C5 H5 118.4 . . ? Fe1 C5 H5 118.4 . . ? C6 P1 C9 91.68(12) . . ? C6 P1 B1 109.49(12) . . ? C9 P1 B1 108.86(12) . . ? C7 C6 C10 125.9(3) . . ? C7 C6 P1 109.64(19) . . ? C10 C6 P1 123.9(2) . . ? C6 C7 C8 114.2(2) . . ? C6 C7 C11 124.4(2) . . ? C8 C7 C11 121.2(2) . . ? C9 C8 C7 114.5(2) . . ? C9 C8 C12 124.6(2) . . ? C7 C8 C12 120.9(2) . . ? C8 C9 C13 126.8(3) . . ? C8 C9 P1 109.29(19) . . ? C13 C9 P1 123.7(2) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 C3 Fe1 B1 C1 66.65(15) . . . . ? C3 Fe1 B1 C1 -113.35(15) 3_575 . . . ? C2 Fe1 B1 C1 -151.53(14) 3_575 . . . ? C2 Fe1 B1 C1 28.47(14) . . . . ? C4 Fe1 B1 C1 -75.37(16) 3_575 . . . ? C4 Fe1 B1 C1 104.63(16) . . . . ? C1 Fe1 B1 C1 180.0 3_575 . . . ? C5 Fe1 B1 C1 -47.2(2) 3_575 . . . ? C5 Fe1 B1 C1 132.8(2) . . . . ? B1 Fe1 B1 C1 -57.0(17) 3_575 . . . ? C3 Fe1 B1 C5 -66.11(15) . . . . ? C3 Fe1 B1 C5 113.89(15) 3_575 . . . ? C2 Fe1 B1 C5 75.71(16) 3_575 . . . ? C2 Fe1 B1 C5 -104.28(16) . . . . ? C4 Fe1 B1 C5 151.88(15) 3_575 . . . ? C4 Fe1 B1 C5 -28.12(15) . . . . ? C1 Fe1 B1 C5 47.2(2) 3_575 . . . ? C1 Fe1 B1 C5 -132.8(2) . . . . ? C5 Fe1 B1 C5 180.0 3_575 . . . ? B1 Fe1 B1 C5 170.2(16) 3_575 . . . ? C3 Fe1 B1 P1 -179.9(2) . . . . ? C3 Fe1 B1 P1 0.1(2) 3_575 . . . ? C2 Fe1 B1 P1 -38.1(2) 3_575 . . . ? C2 Fe1 B1 P1 141.9(2) . . . . ? C4 Fe1 B1 P1 38.1(2) 3_575 . . . ? C4 Fe1 B1 P1 -141.9(2) . . . . ? C1 Fe1 B1 P1 -66.6(3) 3_575 . . . ? C1 Fe1 B1 P1 113.4(3) . . . . ? C5 Fe1 B1 P1 66.2(3) 3_575 . . . ? C5 Fe1 B1 P1 -113.8(3) . . . . ? B1 Fe1 B1 P1 56.4(16) 3_575 . . . ? C5 B1 C1 C2 -4.0(3) . . . . ? P1 B1 C1 C2 178.54(18) . . . . ? Fe1 B1 C1 C2 -51.6(2) . . . . ? C5 B1 C1 Fe1 47.54(18) . . . . ? P1 B1 C1 Fe1 -129.89(18) . . . . ? C3 Fe1 C1 C2 28.60(16) . . . . ? C3 Fe1 C1 C2 -151.41(16) 3_575 . . . ? C2 Fe1 C1 C2 180.0 3_575 . . . ? C4 Fe1 C1 C2 -113.30(16) 3_575 . . . ? C4 Fe1 C1 C2 66.70(16) . . . . ? C1 Fe1 C1 C2 93.2(8) 3_575 . . . ? C5 Fe1 C1 C2 -75.72(17) 3_575 . . . ? C5 Fe1 C1 C2 104.27(17) . . . . ? B1 Fe1 C1 C2 -45.9(2) 3_575 . . . ? B1 Fe1 C1 C2 134.1(2) . . . . ? C3 Fe1 C1 B1 -105.50(16) . . . . ? C3 Fe1 C1 B1 74.50(16) 3_575 . . . ? C2 Fe1 C1 B1 45.9(2) 3_575 . . . ? C2 Fe1 C1 B1 -134.1(2) . . . . ? C4 Fe1 C1 B1 112.61(15) 3_575 . . . ? C4 Fe1 C1 B1 -67.40(15) . . . . ? C1 Fe1 C1 B1 -40.9(8) 3_575 . . . ? C5 Fe1 C1 B1 150.18(14) 3_575 . . . ? C5 Fe1 C1 B1 -29.82(14) . . . . ? B1 Fe1 C1 B1 180.0 3_575 . . . ? B1 C1 C2 C3 2.2(4) . . . . ? Fe1 C1 C2 C3 -51.5(2) . . . . ? B1 C1 C2 Fe1 53.7(2) . . . . ? C3 Fe1 C2 C1 -134.7(2) . . . . ? C3 Fe1 C2 C1 45.3(2) 3_575 . . . ? C2 Fe1 C2 C1 -154(3) 3_575 . . . ? C4 Fe1 C2 C1 74.43(16) 3_575 . . . ? C4 Fe1 C2 C1 -105.57(16) . . . . ? C1 Fe1 C2 C1 180.0 3_575 . . . ? C5 Fe1 C2 C1 111.77(16) 3_575 . . . ? C5 Fe1 C2 C1 -68.23(16) . . . . ? B1 Fe1 C2 C1 150.74(15) 3_575 . . . ? B1 Fe1 C2 C1 -29.26(15) . . . . ? C3 Fe1 C2 C3 180.0 3_575 . . . ? C2 Fe1 C2 C3 -19(3) 3_575 . . . ? C4 Fe1 C2 C3 -150.90(14) 3_575 . . . ? C4 Fe1 C2 C3 29.09(14) . . . . ? C1 Fe1 C2 C3 -45.3(2) 3_575 . . . ? C1 Fe1 C2 C3 134.7(2) . . . . ? C5 Fe1 C2 C3 -113.56(15) 3_575 . . . ? C5 Fe1 C2 C3 66.44(15) . . . . ? B1 Fe1 C2 C3 -74.59(16) 3_575 . . . ? B1 Fe1 C2 C3 105.41(16) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? Fe1 C2 C3 C4 -52.5(2) . . . . ? C1 C2 C3 Fe1 52.5(2) . . . . ? C3 Fe1 C3 C2 -56(13) 3_575 . . . ? C2 Fe1 C3 C2 180.0 3_575 . . . ? C4 Fe1 C3 C2 46.4(2) 3_575 . . . ? C4 Fe1 C3 C2 -133.6(2) . . . . ? C1 Fe1 C3 C2 151.77(14) 3_575 . . . ? C1 Fe1 C3 C2 -28.24(14) . . . . ? C5 Fe1 C3 C2 74.42(16) 3_575 . . . ? C5 Fe1 C3 C2 -105.58(16) . . . . ? B1 Fe1 C3 C2 113.00(16) 3_575 . . . ? B1 Fe1 C3 C2 -67.00(16) . . . . ? C3 Fe1 C3 C4 77(13) 3_575 . . . ? C2 Fe1 C3 C4 -46.4(2) 3_575 . . . ? C2 Fe1 C3 C4 133.6(2) . . . . ? C4 Fe1 C3 C4 180.001(1) 3_575 . . . ? C1 Fe1 C3 C4 -74.66(16) 3_575 . . . ? C1 Fe1 C3 C4 105.34(16) . . . . ? C5 Fe1 C3 C4 -152.01(15) 3_575 . . . ? C5 Fe1 C3 C4 27.99(15) . . . . ? B1 Fe1 C3 C4 -113.43(16) 3_575 . . . ? B1 Fe1 C3 C4 66.57(16) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? Fe1 C3 C4 C5 -52.0(2) . . . . ? C2 C3 C4 Fe1 52.2(2) . . . . ? C3 Fe1 C4 C5 134.9(2) . . . . ? C3 Fe1 C4 C5 -45.1(2) 3_575 . . . ? C2 Fe1 C4 C5 -74.32(17) 3_575 . . . ? C2 Fe1 C4 C5 105.68(17) . . . . ? C4 Fe1 C4 C5 -156(5) 3_575 . . . ? C1 Fe1 C4 C5 -111.97(16) 3_575 . . . ? C1 Fe1 C4 C5 68.03(16) . . . . ? C5 Fe1 C4 C5 180.000(2) 3_575 . . . ? B1 Fe1 C4 C5 -150.95(15) 3_575 . . . ? B1 Fe1 C4 C5 29.05(15) . . . . ? C3 Fe1 C4 C3 180.001(1) 3_575 . . . ? C2 Fe1 C4 C3 150.83(15) 3_575 . . . ? C2 Fe1 C4 C3 -29.17(15) . . . . ? C4 Fe1 C4 C3 69(5) 3_575 . . . ? C1 Fe1 C4 C3 113.18(15) 3_575 . . . ? C1 Fe1 C4 C3 -66.82(15) . . . . ? C5 Fe1 C4 C3 45.1(2) 3_575 . . . ? C5 Fe1 C4 C3 -134.9(2) . . . . ? B1 Fe1 C4 C3 74.19(17) 3_575 . . . ? B1 Fe1 C4 C3 -105.81(17) . . . . ? C3 C4 C5 B1 -2.4(4) . . . . ? Fe1 C4 C5 B1 -53.3(2) . . . . ? C3 C4 C5 Fe1 50.8(2) . . . . ? C1 B1 C5 C4 4.2(3) . . . . ? P1 B1 C5 C4 -178.40(19) . . . . ? Fe1 B1 C5 C4 51.5(2) . . . . ? C1 B1 C5 Fe1 -47.31(18) . . . . ? P1 B1 C5 Fe1 130.12(18) . . . . ? C3 Fe1 C5 C4 -28.47(16) . . . . ? C3 Fe1 C5 C4 151.53(16) 3_575 . . . ? C2 Fe1 C5 C4 113.36(16) 3_575 . . . ? C2 Fe1 C5 C4 -66.64(16) . . . . ? C4 Fe1 C5 C4 180.000(2) 3_575 . . . ? C1 Fe1 C5 C4 75.44(17) 3_575 . . . ? C1 Fe1 C5 C4 -104.56(17) . . . . ? C5 Fe1 C5 C4 -6(3) 3_575 . . . ? B1 Fe1 C5 C4 45.6(2) 3_575 . . . ? B1 Fe1 C5 C4 -134.4(2) . . . . ? C3 Fe1 C5 B1 105.98(16) . . . . ? C3 Fe1 C5 B1 -74.02(16) 3_575 . . . ? C2 Fe1 C5 B1 -112.20(16) 3_575 . . . ? C2 Fe1 C5 B1 67.81(16) . . . . ? C4 Fe1 C5 B1 -45.6(2) 3_575 . . . ? C4 Fe1 C5 B1 134.4(2) . . . . ? C1 Fe1 C5 B1 -150.12(14) 3_575 . . . ? C1 Fe1 C5 B1 29.88(14) . . . . ? C5 Fe1 C5 B1 128(3) 3_575 . . . ? B1 Fe1 C5 B1 180.000(1) 3_575 . . . ? C1 B1 P1 C6 141.7(2) . . . . ? C5 B1 P1 C6 -35.5(2) . . . . ? Fe1 B1 P1 C6 53.5(2) . . . . ? C1 B1 P1 C9 42.9(2) . . . . ? C5 B1 P1 C9 -134.3(2) . . . . ? Fe1 B1 P1 C9 -45.4(2) . . . . ? C9 P1 C6 C7 -7.72(19) . . . . ? B1 P1 C6 C7 -118.41(19) . . . . ? C9 P1 C6 C10 -179.2(2) . . . . ? B1 P1 C6 C10 70.1(2) . . . . ? C10 C6 C7 C8 177.5(2) . . . . ? P1 C6 C7 C8 6.2(3) . . . . ? C10 C6 C7 C11 0.9(4) . . . . ? P1 C6 C7 C11 -170.4(2) . . . . ? C6 C7 C8 C9 -0.6(3) . . . . ? C11 C7 C8 C9 176.1(2) . . . . ? C6 C7 C8 C12 180.0(2) . . . . ? C11 C7 C8 C12 -3.3(4) . . . . ? C7 C8 C9 C13 179.8(2) . . . . ? C12 C8 C9 C13 -0.9(4) . . . . ? C7 C8 C9 P1 -5.3(3) . . . . ? C12 C8 C9 P1 174.1(2) . . . . ? C6 P1 C9 C8 7.34(19) . . . . ? B1 P1 C9 C8 118.61(19) . . . . ? C6 P1 C9 C13 -177.5(2) . . . . ? B1 P1 C9 C13 -66.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 72.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.256 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.053 # Attachment '2-Cu.cif' data_frede72 _database_code_depnum_ccdc_archive 'CCDC 780139' #TrackingRef '2-Cu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H33 B Li N2 P' _chemical_formula_weight 338.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Li Li 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P21/n 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 8.7343(5) _cell_length_b 18.1187(9) _cell_length_c 13.3941(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.630(3) _cell_angle_gamma 90.00 _cell_volume 2109.45(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.065 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 1.138 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7878 _exptl_absorpt_correction_T_max 0.8850 _exptl_absorpt_process_details 'XPREP (Bruker, 2005a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX II CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24605 _diffrn_reflns_av_R_equivalents 0.0791 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 69.37 _reflns_number_total 3932 _reflns_number_gt 2327 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 (Bruker, 2005b)' _computing_cell_refinement 'APEX 2 (Bruker, 2005b)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.1073P)^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 3932 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1671 _refine_ls_wR_factor_gt 0.1502 _refine_ls_goodness_of_fit_ref 0.907 _refine_ls_restrained_S_all 0.907 _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 P1 P 0.82644(8) 0.07592(4) 0.87519(6) 0.0526(2) Uani 1 1 d . . . C1 C 0.9129(3) 0.07901(14) 0.7605(2) 0.0587(7) Uani 1 1 d . . . C2 C 0.8131(4) 0.05611(15) 0.6839(2) 0.0627(8) Uani 1 1 d . . . C3 C 0.6573(3) 0.04127(14) 0.7124(2) 0.0595(7) Uani 1 1 d . . . C4 C 0.6436(3) 0.05466(14) 0.8106(2) 0.0557(7) Uani 1 1 d . . . C5 C 1.0799(3) 0.09839(17) 0.7555(3) 0.0784(10) Uani 1 1 d . . . H5A H 1.1211 0.0694 0.7025 0.118 Uiso 1 1 calc R . . H5B H 1.1381 0.0873 0.8201 0.118 Uiso 1 1 calc R . . H5C H 1.0889 0.1511 0.7408 0.118 Uiso 1 1 calc R . . C6 C 0.8473(5) 0.04543(19) 0.5767(3) 0.0918(12) Uani 1 1 d . . . H6A H 0.9558 0.0567 0.5708 0.138 Uiso 1 1 calc R . . H6B H 0.7822 0.0785 0.5330 0.138 Uiso 1 1 calc R . . H6C H 0.8261 -0.0059 0.5566 0.138 Uiso 1 1 calc R . . C7 C 0.5333(4) 0.01270(18) 0.6380(3) 0.0844(10) Uani 1 1 d . . . H7A H 0.4368 0.0094 0.6694 0.127 Uiso 1 1 calc R . . H7B H 0.5618 -0.0364 0.6152 0.127 Uiso 1 1 calc R . . H7C H 0.5199 0.0463 0.5805 0.127 Uiso 1 1 calc R . . C8 C 0.4990(3) 0.04495(18) 0.8624(3) 0.0743(9) Uani 1 1 d . . . H8A H 0.4660 0.0930 0.8863 0.111 Uiso 1 1 calc R . . H8B H 0.5196 0.0114 0.9195 0.111 Uiso 1 1 calc R . . H8C H 0.4176 0.0242 0.8151 0.111 Uiso 1 1 calc R . . B1 B 0.8195(3) 0.17356(17) 0.9364(2) 0.0514(7) Uani 1 1 d . . . C9 C 0.9340(3) 0.23285(14) 0.9250(2) 0.0547(7) Uani 1 1 d . . . H9 H 1.0137 0.2254 0.8827 0.066 Uiso 1 1 calc R . . C10 C 0.9249(3) 0.29908(15) 0.9760(2) 0.0598(7) Uani 1 1 d . . . H10 H 0.9986 0.3365 0.9672 0.072 Uiso 1 1 calc R . . C11 C 0.8102(3) 0.31250(16) 1.0400(2) 0.0646(8) Uani 1 1 d . . . H11 H 0.8076 0.3583 1.0744 0.078 Uiso 1 1 calc R . . C12 C 0.7005(3) 0.25879(16) 1.0530(2) 0.0633(8) Uani 1 1 d . . . H12 H 0.6219 0.2694 1.0951 0.076 Uiso 1 1 calc R . . C13 C 0.7011(3) 0.19059(15) 1.0071(2) 0.0571(7) Uani 1 1 d . . . H13 H 0.6267 0.1545 1.0202 0.069 Uiso 1 1 calc R . . Li1 Li 0.9482(5) 0.2066(2) 1.1045(4) 0.0554(11) Uani 1 1 d . . . C16 C 1.2556(3) 0.14146(17) 1.0583(3) 0.0735(9) Uani 1 1 d . . . H16A H 1.3632 0.1316 1.0823 0.110 Uiso 1 1 calc R . . H16B H 1.2513 0.1711 0.9968 0.110 Uiso 1 1 calc R . . H16C H 1.2016 0.0946 1.0441 0.110 Uiso 1 1 calc R . . C17 C 1.2607(3) 0.25275(16) 1.1547(3) 0.0709(9) Uani 1 1 d . . . H17A H 1.2085 0.2811 1.2036 0.106 Uiso 1 1 calc R . . H17B H 1.2588 0.2807 1.0919 0.106 Uiso 1 1 calc R . . H17C H 1.3676 0.2437 1.1813 0.106 Uiso 1 1 calc R . . N1 N 1.1817(2) 0.18203(11) 1.13550(18) 0.0546(6) Uani 1 1 d . . . C14 C 1.1880(3) 0.13698(16) 1.2270(2) 0.0638(8) Uani 1 1 d . . . H14A H 1.2944 0.1373 1.2602 0.077 Uiso 1 1 calc R . . H14B H 1.1611 0.0853 1.2086 0.077 Uiso 1 1 calc R . . C15 C 1.0812(3) 0.16452(18) 1.2987(2) 0.0678(8) Uani 1 1 d . . . H15A H 1.0826 0.1300 1.3561 0.081 Uiso 1 1 calc R . . H15B H 1.1175 0.2132 1.3250 0.081 Uiso 1 1 calc R . . N2 N 0.9208(3) 0.17188(12) 1.25125(18) 0.0589(6) Uani 1 1 d . . . C18 C 0.8486(4) 0.09952(18) 1.2412(3) 0.0825(10) Uani 1 1 d . . . H18A H 0.8987 0.0701 1.1923 0.124 Uiso 1 1 calc R . . H18B H 0.7393 0.1053 1.2183 0.124 Uiso 1 1 calc R . . H18C H 0.8593 0.0744 1.3063 0.124 Uiso 1 1 calc R . . C19 C 0.8355(5) 0.2193(2) 1.3135(3) 0.0934(12) Uani 1 1 d . . . H19A H 0.7280 0.2222 1.2849 0.140 Uiso 1 1 calc R . . H19B H 0.8809 0.2688 1.3162 0.140 Uiso 1 1 calc R . . H19C H 0.8400 0.1988 1.3815 0.140 Uiso 1 1 calc R . . 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 P1 0.0448(4) 0.0512(4) 0.0631(5) -0.0002(3) 0.0124(3) -0.0032(3) C1 0.0570(16) 0.0451(14) 0.078(2) 0.0007(14) 0.0250(15) 0.0040(12) C2 0.084(2) 0.0478(15) 0.0595(19) 0.0005(13) 0.0224(17) 0.0116(14) C3 0.0687(19) 0.0465(15) 0.0624(19) -0.0035(13) 0.0017(15) 0.0071(13) C4 0.0510(15) 0.0500(14) 0.0664(19) -0.0018(13) 0.0069(13) -0.0011(12) C5 0.065(2) 0.0598(17) 0.117(3) -0.0023(18) 0.0471(19) -0.0022(15) C6 0.135(3) 0.074(2) 0.072(2) -0.0005(18) 0.035(2) 0.021(2) C7 0.100(3) 0.0633(19) 0.085(2) -0.0113(17) -0.017(2) 0.0131(18) C8 0.0501(17) 0.078(2) 0.096(2) -0.0121(18) 0.0130(16) -0.0102(15) B1 0.0468(16) 0.0545(17) 0.0522(18) 0.0034(15) 0.0024(14) 0.0021(14) C9 0.0512(15) 0.0564(16) 0.0578(17) 0.0053(13) 0.0115(13) -0.0016(12) C10 0.0583(17) 0.0517(16) 0.0686(19) 0.0050(14) 0.0024(14) -0.0061(13) C11 0.0614(18) 0.0556(16) 0.076(2) -0.0069(15) 0.0015(16) 0.0060(14) C12 0.0484(15) 0.0729(19) 0.070(2) -0.0070(16) 0.0109(14) 0.0071(14) C13 0.0419(14) 0.0625(17) 0.0672(18) -0.0036(14) 0.0073(13) -0.0030(12) Li1 0.046(2) 0.058(2) 0.062(3) 0.002(2) 0.009(2) 0.001(2) C16 0.0583(18) 0.078(2) 0.088(2) -0.0005(18) 0.0227(17) 0.0089(15) C17 0.0633(19) 0.0647(18) 0.085(2) 0.0063(16) 0.0104(16) -0.0144(15) N1 0.0444(12) 0.0537(13) 0.0669(15) 0.0039(12) 0.0114(11) -0.0016(10) C14 0.0473(16) 0.0676(18) 0.077(2) 0.0101(16) 0.0062(14) 0.0001(13) C15 0.070(2) 0.0688(18) 0.065(2) 0.0061(15) 0.0068(16) 0.0031(15) N2 0.0539(14) 0.0584(13) 0.0672(15) 0.0016(11) 0.0197(12) 0.0046(11) C18 0.071(2) 0.077(2) 0.101(3) 0.0161(19) 0.0181(19) -0.0145(17) C19 0.103(3) 0.100(2) 0.082(2) 0.002(2) 0.037(2) 0.039(2) _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 P1 C1 1.777(3) . ? P1 C4 1.782(3) . ? P1 B1 1.953(3) . ? C1 C2 1.345(4) . ? C1 C5 1.508(4) . ? C2 C3 1.474(4) . ? C2 C6 1.508(4) . ? C3 C4 1.354(4) . ? C3 C7 1.491(4) . ? C4 C8 1.510(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? B1 C9 1.485(4) . ? B1 C13 1.502(4) . ? B1 Li1 2.489(6) . ? C9 C10 1.387(4) . ? C9 Li1 2.442(5) . ? C9 H9 0.9500 . ? C10 C11 1.402(4) . ? C10 Li1 2.397(5) . ? C10 H10 0.9500 . ? C11 C12 1.389(4) . ? C11 Li1 2.382(5) . ? C11 H11 0.9500 . ? C12 C13 1.380(4) . ? C12 Li1 2.400(5) . ? C12 H12 0.9500 . ? C13 Li1 2.428(5) . ? C13 H13 0.9500 . ? Li1 N1 2.089(5) . ? Li1 N2 2.099(5) . ? C16 N1 1.469(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 N1 1.466(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N1 C14 1.469(4) . ? C14 C15 1.489(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N2 1.486(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? N2 C19 1.453(4) . ? N2 C18 1.455(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 C1 P1 C4 91.35(14) . . ? C1 P1 B1 111.55(13) . . ? C4 P1 B1 109.67(13) . . ? C2 C1 C5 126.5(3) . . ? C2 C1 P1 110.6(2) . . ? C5 C1 P1 122.7(3) . . ? C1 C2 C3 113.8(3) . . ? C1 C2 C6 126.3(3) . . ? C3 C2 C6 119.8(3) . . ? C4 C3 C2 113.0(3) . . ? C4 C3 C7 125.7(3) . . ? C2 C3 C7 121.2(3) . . ? C3 C4 C8 125.7(3) . . ? C3 C4 P1 110.5(2) . . ? C8 C4 P1 123.5(2) . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 B1 C13 115.4(3) . . ? C9 B1 P1 124.3(2) . . ? C13 B1 P1 120.2(2) . . ? C9 B1 Li1 70.75(19) . . ? C13 B1 Li1 69.99(19) . . ? P1 B1 Li1 124.61(17) . . ? C10 C9 B1 120.2(2) . . ? C10 C9 Li1 71.55(19) . . ? B1 C9 Li1 74.21(19) . . ? C10 C9 H9 119.9 . . ? B1 C9 H9 119.9 . . ? Li1 C9 H9 126.2 . . ? C9 C10 C11 122.0(3) . . ? C9 C10 Li1 75.16(19) . . ? C11 C10 Li1 72.37(19) . . ? C9 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? Li1 C10 H10 125.2 . . ? C12 C11 C10 119.9(3) . . ? C12 C11 Li1 73.8(2) . . ? C10 C11 Li1 73.51(19) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? Li1 C11 H11 124.2 . . ? C13 C12 C11 122.6(3) . . ? C13 C12 Li1 74.50(19) . . ? C11 C12 Li1 72.43(19) . . ? C13 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? Li1 C12 H12 126.3 . . ? C12 C13 B1 119.8(2) . . ? C12 C13 Li1 72.28(19) . . ? B1 C13 Li1 74.48(19) . . ? C12 C13 H13 120.1 . . ? B1 C13 H13 120.1 . . ? Li1 C13 H13 124.8 . . ? N1 Li1 N2 87.06(19) . . ? N1 Li1 C11 133.9(2) . . ? N2 Li1 C11 118.8(2) . . ? N1 Li1 C10 107.7(2) . . ? N2 Li1 C10 150.8(2) . . ? C11 Li1 C10 34.12(11) . . ? N1 Li1 C12 167.5(2) . . ? N2 Li1 C12 101.86(19) . . ? C11 Li1 C12 33.77(12) . . ? C10 Li1 C12 60.48(15) . . ? N1 Li1 C13 151.7(2) . . ? N2 Li1 C13 106.90(19) . . ? C11 Li1 C13 60.66(15) . . ? C10 Li1 C13 71.88(16) . . ? C12 Li1 C13 33.22(11) . . ? N1 Li1 C9 101.02(19) . . ? N2 Li1 C9 168.7(2) . . ? C11 Li1 C9 60.72(15) . . ? C10 Li1 C9 33.29(11) . . ? C12 Li1 C9 71.50(16) . . ? C13 Li1 C9 62.44(15) . . ? N1 Li1 B1 118.3(2) . . ? N2 Li1 B1 133.8(2) . . ? C11 Li1 B1 72.43(17) . . ? C10 Li1 B1 61.26(15) . . ? C12 Li1 B1 61.33(15) . . ? C13 Li1 B1 35.54(11) . . ? C9 Li1 B1 35.04(11) . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C17 N1 C16 109.2(2) . . ? C17 N1 C14 111.1(2) . . ? C16 N1 C14 109.1(2) . . ? C17 N1 Li1 106.4(2) . . ? C16 N1 Li1 117.1(2) . . ? C14 N1 Li1 103.9(2) . . ? N1 C14 C15 112.2(2) . . ? N1 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? N1 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? N2 C15 C14 112.2(2) . . ? N2 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? N2 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C19 N2 C18 110.1(3) . . ? C19 N2 C15 108.8(3) . . ? C18 N2 C15 109.9(2) . . ? C19 N2 Li1 118.2(2) . . ? C18 N2 Li1 105.8(2) . . ? C15 N2 Li1 103.81(19) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 C4 P1 C1 C2 -7.5(2) . . . . ? B1 P1 C1 C2 -119.3(2) . . . . ? C4 P1 C1 C5 177.6(2) . . . . ? B1 P1 C1 C5 65.8(2) . . . . ? C5 C1 C2 C3 179.9(3) . . . . ? P1 C1 C2 C3 5.2(3) . . . . ? C5 C1 C2 C6 -0.4(5) . . . . ? P1 C1 C2 C6 -175.0(2) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C6 C2 C3 C4 -178.8(3) . . . . ? C1 C2 C3 C7 -177.6(3) . . . . ? C6 C2 C3 C7 2.6(4) . . . . ? C2 C3 C4 C8 179.9(3) . . . . ? C7 C3 C4 C8 -1.6(5) . . . . ? C2 C3 C4 P1 -6.6(3) . . . . ? C7 C3 C4 P1 171.9(2) . . . . ? C1 P1 C4 C3 8.0(2) . . . . ? B1 P1 C4 C3 121.5(2) . . . . ? C1 P1 C4 C8 -178.2(2) . . . . ? B1 P1 C4 C8 -64.8(3) . . . . ? C1 P1 B1 C9 -30.0(3) . . . . ? C4 P1 B1 C9 -129.7(3) . . . . ? C1 P1 B1 C13 155.4(2) . . . . ? C4 P1 B1 C13 55.7(3) . . . . ? C1 P1 B1 Li1 -119.2(2) . . . . ? C4 P1 B1 Li1 141.15(19) . . . . ? C13 B1 C9 C10 -1.5(4) . . . . ? P1 B1 C9 C10 -176.3(2) . . . . ? Li1 B1 C9 C10 -56.9(3) . . . . ? C13 B1 C9 Li1 55.5(2) . . . . ? P1 B1 C9 Li1 -119.3(2) . . . . ? B1 C9 C10 C11 0.6(4) . . . . ? Li1 C9 C10 C11 -57.6(3) . . . . ? B1 C9 C10 Li1 58.2(3) . . . . ? C9 C10 C11 C12 -0.7(4) . . . . ? Li1 C10 C11 C12 -59.6(3) . . . . ? C9 C10 C11 Li1 59.0(3) . . . . ? C10 C11 C12 C13 1.9(5) . . . . ? Li1 C11 C12 C13 -57.6(3) . . . . ? C10 C11 C12 Li1 59.5(3) . . . . ? C11 C12 C13 B1 -2.8(4) . . . . ? Li1 C12 C13 B1 -59.5(3) . . . . ? C11 C12 C13 Li1 56.7(3) . . . . ? C9 B1 C13 C12 2.6(4) . . . . ? P1 B1 C13 C12 177.6(2) . . . . ? Li1 B1 C13 C12 58.4(3) . . . . ? C9 B1 C13 Li1 -55.9(2) . . . . ? P1 B1 C13 Li1 119.2(2) . . . . ? C12 C11 Li1 N1 177.0(4) . . . . ? C10 C11 Li1 N1 48.2(3) . . . . ? C12 C11 Li1 N2 -66.5(3) . . . . ? C10 C11 Li1 N2 164.7(3) . . . . ? C12 C11 Li1 C10 128.8(3) . . . . ? C10 C11 Li1 C12 -128.8(3) . . . . ? C12 C11 Li1 C13 27.65(17) . . . . ? C10 C11 Li1 C13 -101.2(2) . . . . ? C12 C11 Li1 C9 100.6(2) . . . . ? C10 C11 Li1 C9 -28.22(16) . . . . ? C12 C11 Li1 B1 64.41(19) . . . . ? C10 C11 Li1 B1 -64.42(18) . . . . ? C9 C10 Li1 N1 83.1(2) . . . . ? C11 C10 Li1 N1 -145.7(3) . . . . ? C9 C10 Li1 N2 -159.5(5) . . . . ? C11 C10 Li1 N2 -28.2(5) . . . . ? C9 C10 Li1 C11 -131.3(3) . . . . ? C9 C10 Li1 C12 -101.42(19) . . . . ? C11 C10 Li1 C12 29.84(17) . . . . ? C9 C10 Li1 C13 -67.14(18) . . . . ? C11 C10 Li1 C13 64.13(18) . . . . ? C11 C10 Li1 C9 131.3(3) . . . . ? C9 C10 Li1 B1 -29.99(16) . . . . ? C11 C10 Li1 B1 101.3(2) . . . . ? C13 C12 Li1 N1 122.4(12) . . . . ? C11 C12 Li1 N1 -10.0(12) . . . . ? C13 C12 Li1 N2 -102.8(2) . . . . ? C11 C12 Li1 N2 124.8(2) . . . . ? C13 C12 Li1 C11 132.4(3) . . . . ? C13 C12 Li1 C10 102.3(2) . . . . ? C11 C12 Li1 C10 -30.14(17) . . . . ? C11 C12 Li1 C13 -132.4(3) . . . . ? C13 C12 Li1 C9 67.70(18) . . . . ? C11 C12 Li1 C9 -64.70(19) . . . . ? C13 C12 Li1 B1 30.93(17) . . . . ? C11 C12 Li1 B1 -101.5(2) . . . . ? C12 C13 Li1 N1 -157.3(5) . . . . ? B1 C13 Li1 N1 -28.2(5) . . . . ? C12 C13 Li1 N2 85.9(2) . . . . ? B1 C13 Li1 N2 -145.0(2) . . . . ? C12 C13 Li1 C11 -28.09(18) . . . . ? B1 C13 Li1 C11 101.0(2) . . . . ? C12 C13 Li1 C10 -63.47(19) . . . . ? B1 C13 Li1 C10 65.65(18) . . . . ? B1 C13 Li1 C12 129.1(3) . . . . ? C12 C13 Li1 C9 -98.2(2) . . . . ? B1 C13 Li1 C9 30.87(16) . . . . ? C12 C13 Li1 B1 -129.1(3) . . . . ? C10 C9 Li1 N1 -105.5(2) . . . . ? B1 C9 Li1 N1 124.2(2) . . . . ? C10 C9 Li1 N2 119.5(12) . . . . ? B1 C9 Li1 N2 -10.7(12) . . . . ? C10 C9 Li1 C11 28.90(16) . . . . ? B1 C9 Li1 C11 -101.3(2) . . . . ? B1 C9 Li1 C10 -130.2(2) . . . . ? C10 C9 Li1 C12 64.08(18) . . . . ? B1 C9 Li1 C12 -66.17(18) . . . . ? C10 C9 Li1 C13 98.96(19) . . . . ? B1 C9 Li1 C13 -31.29(16) . . . . ? C10 C9 Li1 B1 130.2(2) . . . . ? C9 B1 Li1 N1 -67.1(3) . . . . ? C13 B1 Li1 N1 165.2(3) . . . . ? P1 B1 Li1 N1 51.8(3) . . . . ? C9 B1 Li1 N2 177.1(3) . . . . ? C13 B1 Li1 N2 49.5(3) . . . . ? P1 B1 Li1 N2 -64.0(4) . . . . ? C9 B1 Li1 C11 63.77(18) . . . . ? C13 B1 Li1 C11 -63.83(18) . . . . ? P1 B1 Li1 C11 -177.3(2) . . . . ? C9 B1 Li1 C10 28.54(15) . . . . ? C13 B1 Li1 C10 -99.07(19) . . . . ? P1 B1 Li1 C10 147.5(2) . . . . ? C9 B1 Li1 C12 98.62(19) . . . . ? C13 B1 Li1 C12 -28.98(16) . . . . ? P1 B1 Li1 C12 -142.4(2) . . . . ? C9 B1 Li1 C13 127.6(2) . . . . ? P1 B1 Li1 C13 -113.5(3) . . . . ? C13 B1 Li1 C9 -127.6(2) . . . . ? P1 B1 Li1 C9 118.9(3) . . . . ? N2 Li1 N1 C17 -102.5(2) . . . . ? C11 Li1 N1 C17 25.8(4) . . . . ? C10 Li1 N1 C17 51.8(3) . . . . ? C12 Li1 N1 C17 33.4(12) . . . . ? C13 Li1 N1 C17 136.3(5) . . . . ? C9 Li1 N1 C17 85.5(2) . . . . ? B1 Li1 N1 C17 118.1(2) . . . . ? N2 Li1 N1 C16 135.2(2) . . . . ? C11 Li1 N1 C16 -96.6(4) . . . . ? C10 Li1 N1 C16 -70.5(3) . . . . ? C12 Li1 N1 C16 -88.9(12) . . . . ? C13 Li1 N1 C16 14.0(6) . . . . ? C9 Li1 N1 C16 -36.8(3) . . . . ? B1 Li1 N1 C16 -4.2(3) . . . . ? N2 Li1 N1 C14 14.9(2) . . . . ? C11 Li1 N1 C14 143.1(3) . . . . ? C10 Li1 N1 C14 169.2(2) . . . . ? C12 Li1 N1 C14 150.8(11) . . . . ? C13 Li1 N1 C14 -106.3(5) . . . . ? C9 Li1 N1 C14 -157.1(2) . . . . ? B1 Li1 N1 C14 -124.5(2) . . . . ? C17 N1 C14 C15 74.7(3) . . . . ? C16 N1 C14 C15 -164.9(2) . . . . ? Li1 N1 C14 C15 -39.3(3) . . . . ? N1 C14 C15 N2 53.8(3) . . . . ? C14 C15 N2 C19 -162.5(3) . . . . ? C14 C15 N2 C18 76.9(3) . . . . ? C14 C15 N2 Li1 -35.8(3) . . . . ? N1 Li1 N2 C19 131.4(3) . . . . ? C11 Li1 N2 C19 -8.4(4) . . . . ? C10 Li1 N2 C19 9.3(6) . . . . ? C12 Li1 N2 C19 -39.7(3) . . . . ? C13 Li1 N2 C19 -73.7(3) . . . . ? C9 Li1 N2 C19 -92.7(12) . . . . ? B1 Li1 N2 C19 -101.2(4) . . . . ? N1 Li1 N2 C18 -104.8(2) . . . . ? C11 Li1 N2 C18 115.4(3) . . . . ? C10 Li1 N2 C18 133.0(5) . . . . ? C12 Li1 N2 C18 84.0(2) . . . . ? C13 Li1 N2 C18 50.1(3) . . . . ? C9 Li1 N2 C18 31.1(12) . . . . ? B1 Li1 N2 C18 22.6(4) . . . . ? N1 Li1 N2 C15 10.9(2) . . . . ? C11 Li1 N2 C15 -128.9(2) . . . . ? C10 Li1 N2 C15 -111.3(5) . . . . ? C12 Li1 N2 C15 -160.3(2) . . . . ? C13 Li1 N2 C15 165.8(2) . . . . ? C9 Li1 N2 C15 146.8(12) . . . . ? B1 Li1 N2 C15 138.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 69.37 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.444 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.054 data_gbc042 _database_code_depnum_ccdc_archive 'CCDC 780140' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H41 B Li N2 P Si' _chemical_formula_weight 410.38 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' Li Li -0.0003 0.0001 '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' Si Si 0.0817 0.0704 '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 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 10.345(2) _cell_length_b 14.114(3) _cell_length_c 18.403(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.889(3) _cell_angle_gamma 90.00 _cell_volume 2638.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 807 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 15.72 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.033 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9108 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details 'XPREP (Bruker, 2005a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Bruker Smart APEX II CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24522 _diffrn_reflns_av_R_equivalents 0.1957 _diffrn_reflns_av_sigmaI/netI 0.1471 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 24.25 _reflns_number_total 4264 _reflns_number_gt 1749 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 (Bruker, 2005b)' _computing_cell_refinement 'APEX 2 (Bruker, 2005b)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.0492P)^2^+1.0260P] 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 4264 _refine_ls_number_parameters 286 _refine_ls_number_restraints 49 _refine_ls_R_factor_all 0.2018 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.1658 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.047 _refine_ls_shift/su_mean 0.001 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 Li1 Li 0.3229(8) 0.9257(5) 0.2386(5) 0.057(2) Uani 1 1 d D A . B1 B 0.2732(5) 0.7513(4) 0.2308(3) 0.0447(15) Uani 1 1 d . . . Si2 Si 0.33715(16) 0.71552(12) 0.39337(9) 0.0734(6) Uani 1 1 d . . . C1 C 0.1817(5) 0.7537(5) 0.4216(3) 0.097(2) Uani 1 1 d . . . H1A H 0.1820 0.8227 0.4274 0.146 Uiso 1 1 calc R . . H1B H 0.1747 0.7236 0.4687 0.146 Uiso 1 1 calc R . . H1C H 0.1065 0.7349 0.3835 0.146 Uiso 1 1 calc R . . C2 C 0.3320(7) 0.5822(4) 0.3867(4) 0.120(3) Uani 1 1 d . . . H2A H 0.2526 0.5626 0.3520 0.180 Uiso 1 1 calc R . . H2B H 0.3307 0.5551 0.4356 0.180 Uiso 1 1 calc R . . H2C H 0.4101 0.5595 0.3689 0.180 Uiso 1 1 calc R . . C3 C 0.4746(6) 0.7502(5) 0.4700(3) 0.122(3) Uani 1 1 d . . . H3A H 0.5590 0.7336 0.4564 0.182 Uiso 1 1 calc R . . H3B H 0.4656 0.7165 0.5153 0.182 Uiso 1 1 calc R . . H3C H 0.4715 0.8186 0.4783 0.182 Uiso 1 1 calc R . . C4 C 0.3633(5) 0.7647(3) 0.3044(3) 0.0444(13) Uani 1 1 d . . . C5 C 0.4847(5) 0.8106(3) 0.3026(3) 0.0513(13) Uani 1 1 d . . . H5 H 0.5404 0.8300 0.3508 0.062 Uiso 1 1 calc R . . C6 C 0.5220(5) 0.8414(3) 0.2377(3) 0.0538(14) Uani 1 1 d . . . H6 H 0.6061 0.8773 0.2406 0.065 Uiso 1 1 calc R . . C7 C 0.4407(6) 0.8285(3) 0.1701(3) 0.0592(15) Uani 1 1 d . . . H7 H 0.4678 0.8549 0.1248 0.071 Uiso 1 1 calc R . . C8 C 0.3184(5) 0.7855(3) 0.1637(3) 0.0551(14) Uani 1 1 d . . . H8 H 0.2581 0.7822 0.1144 0.066 Uiso 1 1 calc R . . P1 P 0.10035(13) 0.68838(9) 0.22181(8) 0.0545(4) Uani 1 1 d . . . C9 C -0.0190(4) 0.7824(3) 0.2038(3) 0.0501(13) Uani 1 1 d . . . C10 C -0.0871(5) 0.7752(4) 0.1340(3) 0.0564(14) Uani 1 1 d . . . C11 C -0.0431(5) 0.7013(4) 0.0898(3) 0.0562(14) Uani 1 1 d . . . C12 C 0.0601(5) 0.6507(3) 0.1276(3) 0.0553(14) Uani 1 1 d . . . C13 C -0.0442(5) 0.8509(4) 0.2620(3) 0.0759(17) Uani 1 1 d . . . H13A H -0.0975 0.9038 0.2384 0.114 Uiso 1 1 calc R . . H13B H 0.0399 0.8750 0.2894 0.114 Uiso 1 1 calc R . . H13C H -0.0914 0.8185 0.2963 0.114 Uiso 1 1 calc R . . C14 C -0.2032(5) 0.8367(4) 0.1019(3) 0.0829(18) Uani 1 1 d . . . H14A H -0.2189 0.8829 0.1391 0.124 Uiso 1 1 calc R . . H14B H -0.2816 0.7970 0.0875 0.124 Uiso 1 1 calc R . . H14C H -0.1847 0.8702 0.0584 0.124 Uiso 1 1 calc R . . C15 C -0.1084(5) 0.6852(4) 0.0103(3) 0.0827(18) Uani 1 1 d . . . H15A H -0.0657 0.6321 -0.0100 0.124 Uiso 1 1 calc R . . H15B H -0.1002 0.7425 -0.0186 0.124 Uiso 1 1 calc R . . H15C H -0.2018 0.6707 0.0078 0.124 Uiso 1 1 calc R . . C16 C 0.1296(5) 0.5704(4) 0.0977(3) 0.0811(19) Uani 1 1 d . . . H16A H 0.0702 0.5409 0.0560 0.122 Uiso 1 1 calc R . . H16B H 0.1563 0.5232 0.1367 0.122 Uiso 1 1 calc R . . H16C H 0.2077 0.5946 0.0808 0.122 Uiso 1 1 calc R . . N1 N 0.2299(5) 1.0240(3) 0.1592(3) 0.0800(15) Uani 1 1 d D . . N2 N 0.3494(5) 1.0362(3) 0.3141(3) 0.0781(15) Uani 1 1 d D . . C17A C 0.3090(11) 1.0191(13) 0.3850(5) 0.108(4) Uani 0.75 1 d PD A 1 H17A H 0.3223 1.0768 0.4151 0.162 Uiso 0.75 1 calc PR A 1 H17B H 0.3618 0.9675 0.4111 0.162 Uiso 0.75 1 calc PR A 1 H17C H 0.2157 1.0014 0.3762 0.162 Uiso 0.75 1 calc PR A 1 C18A C 0.4893(7) 1.0624(7) 0.3271(5) 0.103(4) Uani 0.75 1 d PD A 1 H18A H 0.5190 1.0657 0.2796 0.154 Uiso 0.75 1 calc PR A 1 H18B H 0.5410 1.0147 0.3587 0.154 Uiso 0.75 1 calc PR A 1 H18C H 0.5012 1.1243 0.3515 0.154 Uiso 0.75 1 calc PR A 1 C19A C 0.2660(13) 1.1133(5) 0.2729(5) 0.096(4) Uani 0.75 1 d PDU A 1 H19A H 0.1736 1.1041 0.2785 0.115 Uiso 0.75 1 calc PR A 1 H19B H 0.2960 1.1753 0.2951 0.115 Uiso 0.75 1 calc PR A 1 C20A C 0.2717(9) 1.1151(5) 0.1941(5) 0.104(3) Uani 0.75 1 d PDU A 1 H20A H 0.3627 1.1291 0.1880 0.125 Uiso 0.75 1 calc PR A 1 H20B H 0.2137 1.1661 0.1694 0.125 Uiso 0.75 1 calc PR A 1 C21A C 0.0866(7) 1.0154(7) 0.1469(5) 0.091(3) Uani 0.75 1 d PD A 1 H21A H 0.0564 1.0254 0.1936 0.136 Uiso 0.75 1 calc PR A 1 H21B H 0.0606 0.9520 0.1279 0.136 Uiso 0.75 1 calc PR A 1 H21C H 0.0467 1.0631 0.1108 0.136 Uiso 0.75 1 calc PR A 1 C22A C 0.2716(10) 1.0187(7) 0.0859(4) 0.115(4) Uani 0.75 1 d PD A 1 H22A H 0.2378 1.0740 0.0560 0.172 Uiso 0.75 1 calc PR A 1 H22B H 0.2363 0.9607 0.0602 0.172 Uiso 0.75 1 calc PR A 1 H22C H 0.3679 1.0178 0.0934 0.172 Uiso 0.75 1 calc PR A 1 C17B C 0.4776(16) 1.043(3) 0.3651(15) 0.108(4) Uani 0.25 1 d PD A 2 H17D H 0.5466 1.0166 0.3412 0.162 Uiso 0.25 1 calc PR A 2 H17E H 0.4740 1.0077 0.4104 0.162 Uiso 0.25 1 calc PR A 2 H17F H 0.4973 1.1099 0.3773 0.162 Uiso 0.25 1 calc PR A 2 C18B C 0.265(4) 1.015(4) 0.3682(17) 0.103(4) Uani 0.25 1 d PD A 2 H18D H 0.2873 1.0579 0.4106 0.154 Uiso 0.25 1 calc PR A 2 H18E H 0.2795 0.9493 0.3851 0.154 Uiso 0.25 1 calc PR A 2 H18F H 0.1726 1.0236 0.3449 0.154 Uiso 0.25 1 calc PR A 2 C19B C 0.305(5) 1.1207(8) 0.2684(11) 0.096(4) Uani 0.25 1 d PDU A 2 H19C H 0.2766 1.1700 0.3004 0.115 Uiso 0.25 1 calc PR A 2 H19D H 0.3796 1.1463 0.2482 0.115 Uiso 0.25 1 calc PR A 2 C20B C 0.196(2) 1.1011(10) 0.2073(8) 0.104(3) Uani 0.25 1 d PDU A 2 H20C H 0.1746 1.1593 0.1775 0.125 Uiso 0.25 1 calc PR A 2 H20D H 0.1174 1.0827 0.2273 0.125 Uiso 0.25 1 calc PR A 2 C21B C 0.1084(18) 0.989(2) 0.1113(18) 0.091(3) Uani 0.25 1 d PD A 2 H21D H 0.0495 0.9627 0.1421 0.136 Uiso 0.25 1 calc PR A 2 H21E H 0.1309 0.9394 0.0785 0.136 Uiso 0.25 1 calc PR A 2 H21F H 0.0644 1.0413 0.0816 0.136 Uiso 0.25 1 calc PR A 2 C22B C 0.338(2) 1.072(2) 0.1313(17) 0.115(4) Uani 0.25 1 d PD A 2 H22D H 0.3142 1.1379 0.1202 0.172 Uiso 0.25 1 calc PR A 2 H22E H 0.3520 1.0397 0.0861 0.172 Uiso 0.25 1 calc PR A 2 H22F H 0.4184 1.0684 0.1689 0.172 Uiso 0.25 1 calc PR A 2 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 Li1 0.058(6) 0.035(5) 0.079(7) -0.013(4) 0.016(5) 0.001(4) B1 0.048(4) 0.028(3) 0.059(4) -0.003(3) 0.012(3) 0.001(3) Si2 0.0622(11) 0.0928(14) 0.0611(11) 0.0207(10) 0.0009(9) -0.0126(10) C1 0.088(5) 0.141(6) 0.070(4) 0.007(4) 0.032(4) -0.018(4) C2 0.113(6) 0.086(5) 0.157(7) 0.062(5) 0.015(5) -0.008(4) C3 0.097(5) 0.192(8) 0.063(4) 0.032(4) -0.016(4) -0.037(5) C4 0.043(3) 0.038(3) 0.054(3) -0.001(2) 0.014(3) 0.001(2) C5 0.044(3) 0.044(3) 0.063(4) -0.006(3) 0.004(3) 0.001(3) C6 0.048(3) 0.046(3) 0.074(4) -0.007(3) 0.027(3) -0.003(3) C7 0.079(4) 0.048(4) 0.060(4) -0.006(3) 0.037(3) -0.004(3) C8 0.062(4) 0.051(3) 0.053(3) -0.011(3) 0.012(3) -0.007(3) P1 0.0483(9) 0.0492(9) 0.0643(10) -0.0040(8) 0.0064(7) -0.0074(7) C9 0.037(3) 0.054(3) 0.061(4) -0.005(3) 0.014(3) -0.007(3) C10 0.042(3) 0.058(4) 0.069(4) 0.005(3) 0.009(3) -0.007(3) C11 0.050(3) 0.064(4) 0.053(4) -0.010(3) 0.008(3) -0.015(3) C12 0.053(3) 0.043(3) 0.071(4) -0.009(3) 0.015(3) -0.011(3) C13 0.080(4) 0.071(4) 0.081(4) -0.009(3) 0.024(3) 0.000(3) C14 0.063(4) 0.094(5) 0.088(5) 0.021(4) 0.004(3) 0.013(4) C15 0.073(4) 0.103(5) 0.068(4) -0.008(4) 0.003(3) -0.020(4) C16 0.073(4) 0.066(4) 0.100(5) -0.027(4) 0.007(4) 0.002(3) N1 0.082(4) 0.050(3) 0.110(4) 0.019(3) 0.027(3) 0.000(3) N2 0.058(3) 0.058(3) 0.120(5) -0.031(3) 0.021(3) -0.006(3) C17A 0.098(10) 0.125(9) 0.105(8) -0.065(8) 0.030(7) -0.019(9) C18A 0.091(7) 0.078(7) 0.141(9) -0.065(7) 0.028(6) -0.029(5) C19A 0.115(10) 0.039(4) 0.145(7) -0.016(5) 0.057(6) 0.016(5) C20A 0.090(6) 0.077(5) 0.141(6) 0.024(5) 0.013(5) 0.000(5) C21A 0.083(6) 0.059(7) 0.126(11) -0.001(6) 0.008(6) 0.005(5) C22A 0.127(10) 0.130(10) 0.094(9) 0.061(7) 0.038(7) 0.018(7) C17B 0.098(10) 0.125(9) 0.105(8) -0.065(8) 0.030(7) -0.019(9) C18B 0.091(7) 0.078(7) 0.141(9) -0.065(7) 0.028(6) -0.029(5) C19B 0.115(10) 0.039(4) 0.145(7) -0.016(5) 0.057(6) 0.016(5) C20B 0.090(6) 0.077(5) 0.141(6) 0.024(5) 0.013(5) 0.000(5) C21B 0.083(6) 0.059(7) 0.126(11) -0.001(6) 0.008(6) 0.005(5) C22B 0.127(10) 0.130(10) 0.094(9) 0.061(7) 0.038(7) 0.018(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 Li1 N2 2.072(9) . ? Li1 N1 2.111(10) . ? Li1 C7 2.353(9) . ? Li1 C6 2.381(9) . ? Li1 C8 2.407(9) . ? Li1 C5 2.465(9) . ? Li1 B1 2.513(9) . ? Li1 C4 2.571(9) . ? B1 C8 1.482(7) . ? B1 C4 1.504(7) . ? B1 P1 1.975(6) . ? Si2 C4 1.845(5) . ? Si2 C1 1.861(6) . ? Si2 C3 1.868(6) . ? Si2 C2 1.886(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.418(6) . ? C5 C6 1.391(6) . ? C5 H5 1.0000 . ? C6 C7 1.376(6) . ? C6 H6 1.0000 . ? C7 C8 1.389(6) . ? C7 H7 1.0000 . ? C8 H8 1.0000 . ? P1 C12 1.787(5) . ? P1 C9 1.800(5) . ? C9 C10 1.346(6) . ? C9 C13 1.502(6) . ? C10 C11 1.449(7) . ? C10 C14 1.510(6) . ? C11 C12 1.361(6) . ? C11 C15 1.508(6) . ? C12 C16 1.502(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1 C21A 1.462(6) . ? N1 C20A 1.466(7) . ? N1 C22B 1.474(9) . ? N1 C21B 1.477(9) . ? N1 C20B 1.486(9) . ? N1 C22A 1.494(6) . ? N2 C17A 1.463(7) . ? N2 C18A 1.469(6) . ? N2 C18B 1.472(9) . ? N2 C17B 1.475(9) . ? N2 C19B 1.483(9) . ? N2 C19A 1.503(7) . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C18A H18A 0.9800 . ? C18A H18B 0.9800 . ? C18A H18C 0.9800 . ? C19A C20A 1.462(12) . ? C19A H19A 0.9900 . ? C19A H19B 0.9900 . ? C20A H20A 0.9900 . ? C20A H20B 0.9900 . ? C21A H21A 0.9800 . ? C21A H21B 0.9800 . ? C21A H21C 0.9800 . ? C22A H22A 0.9800 . ? C22A H22B 0.9800 . ? C22A H22C 0.9800 . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C18B H18D 0.9800 . ? C18B H18E 0.9800 . ? C18B H18F 0.9800 . ? C19B C20B 1.456(16) . ? C19B H19C 0.9900 . ? C19B H19D 0.9900 . ? C20B H20C 0.9900 . ? C20B H20D 0.9900 . ? C21B H21D 0.9800 . ? C21B H21E 0.9800 . ? C21B H21F 0.9800 . ? C22B H22D 0.9800 . ? C22B H22E 0.9800 . ? C22B H22F 0.9800 . ? 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 N2 Li1 N1 87.4(3) . . ? N2 Li1 C7 141.4(4) . . ? N1 Li1 C7 103.1(4) . . ? N2 Li1 C6 112.1(4) . . ? N1 Li1 C6 127.3(4) . . ? C7 Li1 C6 33.79(19) . . ? N2 Li1 C8 171.3(5) . . ? N1 Li1 C8 100.7(4) . . ? C7 Li1 C8 33.89(19) . . ? C6 Li1 C8 60.6(2) . . ? N2 Li1 C5 100.6(4) . . ? N1 Li1 C5 160.6(5) . . ? C7 Li1 C5 59.9(3) . . ? C6 Li1 C5 33.31(18) . . ? C8 Li1 C5 70.8(3) . . ? N2 Li1 B1 140.8(5) . . ? N1 Li1 B1 122.8(4) . . ? C7 Li1 B1 61.3(3) . . ? C6 Li1 B1 71.2(3) . . ? C8 Li1 B1 34.98(19) . . ? C5 Li1 B1 59.7(2) . . ? N2 Li1 C4 111.1(4) . . ? N1 Li1 C4 156.8(4) . . ? C7 Li1 C4 71.5(3) . . ? C6 Li1 C4 59.9(2) . . ? C8 Li1 C4 61.8(2) . . ? C5 Li1 C4 32.64(17) . . ? B1 Li1 C4 34.40(19) . . ? C8 B1 C4 118.0(5) . . ? C8 B1 P1 120.0(4) . . ? C4 B1 P1 122.0(4) . . ? C8 B1 Li1 68.6(3) . . ? C4 B1 Li1 74.9(3) . . ? P1 B1 Li1 128.1(3) . . ? C4 Si2 C1 114.7(2) . . ? C4 Si2 C3 110.6(3) . . ? C1 Si2 C3 106.8(3) . . ? C4 Si2 C2 108.9(3) . . ? C1 Si2 C2 107.0(3) . . ? C3 Si2 C2 108.6(3) . . ? Si2 C1 H1A 109.5 . . ? Si2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Si2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? Si2 C2 H2A 109.5 . . ? Si2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Si2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? Si2 C3 H3A 109.5 . . ? Si2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? Si2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 B1 116.0(4) . . ? C5 C4 Si2 118.1(4) . . ? B1 C4 Si2 125.5(4) . . ? C5 C4 Li1 69.6(3) . . ? B1 C4 Li1 70.7(3) . . ? Si2 C4 Li1 135.4(3) . . ? C6 C5 C4 123.5(5) . . ? C6 C5 Li1 70.0(3) . . ? C4 C5 Li1 77.8(3) . . ? C6 C5 H5 117.9 . . ? C4 C5 H5 117.9 . . ? Li1 C5 H5 117.9 . . ? C7 C6 C5 120.9(5) . . ? C7 C6 Li1 72.0(3) . . ? C5 C6 Li1 76.7(3) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? Li1 C6 H6 119.5 . . ? C6 C7 C8 121.8(5) . . ? C6 C7 Li1 74.2(3) . . ? C8 C7 Li1 75.2(3) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? Li1 C7 H7 119.1 . . ? C7 C8 B1 119.8(5) . . ? C7 C8 Li1 70.9(3) . . ? B1 C8 Li1 76.4(3) . . ? C7 C8 H8 120.0 . . ? B1 C8 H8 120.0 . . ? Li1 C8 H8 120.0 . . ? C12 P1 C9 90.8(3) . . ? C12 P1 B1 104.9(2) . . ? C9 P1 B1 105.2(2) . . ? C10 C9 C13 126.8(5) . . ? C10 C9 P1 109.7(4) . . ? C13 C9 P1 123.2(4) . . ? C9 C10 C11 115.3(5) . . ? C9 C10 C14 124.3(5) . . ? C11 C10 C14 120.4(5) . . ? C12 C11 C10 112.9(5) . . ? C12 C11 C15 125.6(5) . . ? C10 C11 C15 121.5(5) . . ? C11 C12 C16 126.4(5) . . ? C11 C12 P1 110.9(4) . . ? C16 C12 P1 122.7(4) . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C21A N1 C20A 110.3(6) . . ? C21A N1 C22B 142.6(13) . . ? C20A N1 C22B 64.8(14) . . ? C21A N1 C21B 32.4(12) . . ? C20A N1 C21B 134.6(14) . . ? C22B N1 C21B 124(2) . . ? C21A N1 C20B 78.9(10) . . ? C20A N1 C20B 34.8(10) . . ? C22B N1 C20B 98.8(18) . . ? C21B N1 C20B 109.4(15) . . ? C21A N1 C22A 108.2(7) . . ? C20A N1 C22A 109.1(6) . . ? C22B N1 C22A 48.8(13) . . ? C21B N1 C22A 78.6(14) . . ? C20B N1 C22A 135.7(9) . . ? C21A N1 Li1 111.7(6) . . ? C20A N1 Li1 102.5(5) . . ? C22B N1 Li1 105.4(12) . . ? C21B N1 Li1 114.7(16) . . ? C20B N1 Li1 101.3(6) . . ? C22A N1 Li1 114.9(5) . . ? C17A N2 C18A 109.7(6) . . ? C17A N2 C18B 19.7(19) . . ? C18A N2 C18B 129.3(18) . . ? C17A N2 C17B 79.6(14) . . ? C18A N2 C17B 30.8(14) . . ? C18B N2 C17B 99(2) . . ? C17A N2 C19B 121.8(19) . . ? C18A N2 C19B 95(2) . . ? C18B N2 C19B 113(3) . . ? C17B N2 C19B 117(2) . . ? C17A N2 C19A 109.7(10) . . ? C18A N2 C19A 110.7(8) . . ? C18B N2 C19A 98(2) . . ? C17B N2 C19A 129.3(18) . . ? C19B N2 C19A 17(3) . . ? C17A N2 Li1 116.7(7) . . ? C18A N2 Li1 107.4(5) . . ? C18B N2 Li1 106.2(19) . . ? C17B N2 Li1 117.7(15) . . ? C19B N2 Li1 103.7(6) . . ? C19A N2 Li1 102.5(4) . . ? N2 C17A H17A 109.5 . . ? N2 C17A H17B 109.5 . . ? N2 C17A H17C 109.5 . . ? N2 C18A H18A 109.5 . . ? N2 C18A H18B 109.5 . . ? N2 C18A H18C 109.5 . . ? C20A C19A N2 112.8(7) . . ? C20A C19A H19A 109.0 . . ? N2 C19A H19A 109.0 . . ? C20A C19A H19B 109.0 . . ? N2 C19A H19B 109.0 . . ? H19A C19A H19B 107.8 . . ? C19A C20A N1 110.8(7) . . ? C19A C20A H20A 109.5 . . ? N1 C20A H20A 109.5 . . ? C19A C20A H20B 109.5 . . ? N1 C20A H20B 109.5 . . ? H20A C20A H20B 108.1 . . ? N1 C21A H21A 109.5 . . ? N1 C21A H21B 109.5 . . ? N1 C21A H21C 109.5 . . ? N1 C22A H22A 109.5 . . ? N1 C22A H22B 109.5 . . ? N1 C22A H22C 109.5 . . ? N2 C17B H17D 109.5 . . ? N2 C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? N2 C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? N2 C18B H18D 109.5 . . ? N2 C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? N2 C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C20B C19B N2 113.5(15) . . ? C20B C19B H19C 108.9 . . ? N2 C19B H19C 108.9 . . ? C20B C19B H19D 108.9 . . ? N2 C19B H19D 108.9 . . ? H19C C19B H19D 107.7 . . ? C19B C20B N1 111.4(13) . . ? C19B C20B H20C 109.3 . . ? N1 C20B H20C 109.3 . . ? C19B C20B H20D 109.3 . . ? N1 C20B H20D 109.3 . . ? H20C C20B H20D 108.0 . . ? N1 C21B H21D 109.5 . . ? N1 C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? N1 C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? N1 C22B H22D 109.5 . . ? N1 C22B H22E 109.5 . . ? H22D C22B H22E 109.5 . . ? N1 C22B H22F 109.5 . . ? H22D C22B H22F 109.5 . . ? H22E C22B H22F 109.5 . . ? 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 N2 Li1 B1 C8 -167.4(7) . . . . ? N1 Li1 B1 C8 57.6(5) . . . . ? C7 Li1 B1 C8 -29.8(3) . . . . ? C6 Li1 B1 C8 -65.2(3) . . . . ? C5 Li1 B1 C8 -99.7(4) . . . . ? C4 Li1 B1 C8 -128.9(4) . . . . ? N2 Li1 B1 C4 -38.5(7) . . . . ? N1 Li1 B1 C4 -173.5(5) . . . . ? C7 Li1 B1 C4 99.2(4) . . . . ? C6 Li1 B1 C4 63.7(3) . . . . ? C8 Li1 B1 C4 128.9(4) . . . . ? C5 Li1 B1 C4 29.2(3) . . . . ? N2 Li1 B1 P1 80.6(8) . . . . ? N1 Li1 B1 P1 -54.4(7) . . . . ? C7 Li1 B1 P1 -141.8(5) . . . . ? C6 Li1 B1 P1 -177.2(4) . . . . ? C8 Li1 B1 P1 -112.0(5) . . . . ? C5 Li1 B1 P1 148.2(5) . . . . ? C4 Li1 B1 P1 119.0(5) . . . . ? C8 B1 C4 C5 0.6(6) . . . . ? P1 B1 C4 C5 179.7(3) . . . . ? Li1 B1 C4 C5 -54.5(4) . . . . ? C8 B1 C4 Si2 -172.2(3) . . . . ? P1 B1 C4 Si2 6.8(6) . . . . ? Li1 B1 C4 Si2 132.6(4) . . . . ? C8 B1 C4 Li1 55.1(4) . . . . ? P1 B1 C4 Li1 -125.8(4) . . . . ? C1 Si2 C4 C5 127.9(4) . . . . ? C3 Si2 C4 C5 7.1(5) . . . . ? C2 Si2 C4 C5 -112.2(4) . . . . ? C1 Si2 C4 B1 -59.3(5) . . . . ? C3 Si2 C4 B1 179.8(4) . . . . ? C2 Si2 C4 B1 60.5(5) . . . . ? C1 Si2 C4 Li1 39.1(5) . . . . ? C3 Si2 C4 Li1 -81.8(5) . . . . ? C2 Si2 C4 Li1 159.0(4) . . . . ? N2 Li1 C4 C5 -76.2(4) . . . . ? N1 Li1 C4 C5 142.7(11) . . . . ? C7 Li1 C4 C5 62.7(3) . . . . ? C6 Li1 C4 C5 27.7(3) . . . . ? C8 Li1 C4 C5 98.3(3) . . . . ? B1 Li1 C4 C5 128.7(4) . . . . ? N2 Li1 C4 B1 155.1(5) . . . . ? N1 Li1 C4 B1 14.0(11) . . . . ? C7 Li1 C4 B1 -65.9(3) . . . . ? C6 Li1 C4 B1 -100.9(4) . . . . ? C8 Li1 C4 B1 -30.4(3) . . . . ? C5 Li1 C4 B1 -128.7(4) . . . . ? N2 Li1 C4 Si2 33.6(6) . . . . ? N1 Li1 C4 Si2 -107.5(11) . . . . ? C7 Li1 C4 Si2 172.6(4) . . . . ? C6 Li1 C4 Si2 137.6(4) . . . . ? C8 Li1 C4 Si2 -151.9(4) . . . . ? C5 Li1 C4 Si2 109.8(5) . . . . ? B1 Li1 C4 Si2 -121.5(5) . . . . ? B1 C4 C5 C6 -0.7(6) . . . . ? Si2 C4 C5 C6 172.8(4) . . . . ? Li1 C4 C5 C6 -55.7(4) . . . . ? B1 C4 C5 Li1 55.0(4) . . . . ? Si2 C4 C5 Li1 -131.5(3) . . . . ? N2 Li1 C5 C6 -114.3(4) . . . . ? N1 Li1 C5 C6 -1.2(13) . . . . ? C7 Li1 C5 C6 29.9(3) . . . . ? C8 Li1 C5 C6 65.4(3) . . . . ? B1 Li1 C5 C6 102.2(4) . . . . ? C4 Li1 C5 C6 132.9(4) . . . . ? N2 Li1 C5 C4 112.8(4) . . . . ? N1 Li1 C5 C4 -134.1(13) . . . . ? C7 Li1 C5 C4 -103.0(3) . . . . ? C6 Li1 C5 C4 -132.9(4) . . . . ? C8 Li1 C5 C4 -67.5(3) . . . . ? B1 Li1 C5 C4 -30.7(3) . . . . ? C4 C5 C6 C7 0.0(7) . . . . ? Li1 C5 C6 C7 -59.2(5) . . . . ? C4 C5 C6 Li1 59.2(5) . . . . ? N2 Li1 C6 C7 -155.6(5) . . . . ? N1 Li1 C6 C7 -51.3(5) . . . . ? C8 Li1 C6 C7 29.5(3) . . . . ? C5 Li1 C6 C7 129.2(5) . . . . ? B1 Li1 C6 C7 66.2(3) . . . . ? C4 Li1 C6 C7 102.0(3) . . . . ? N2 Li1 C6 C5 75.2(5) . . . . ? N1 Li1 C6 C5 179.5(5) . . . . ? C7 Li1 C6 C5 -129.2(5) . . . . ? C8 Li1 C6 C5 -99.8(3) . . . . ? B1 Li1 C6 C5 -63.1(3) . . . . ? C4 Li1 C6 C5 -27.2(3) . . . . ? C5 C6 C7 C8 0.7(7) . . . . ? Li1 C6 C7 C8 -60.9(5) . . . . ? C5 C6 C7 Li1 61.5(5) . . . . ? N2 Li1 C7 C6 37.8(7) . . . . ? N1 Li1 C7 C6 140.4(4) . . . . ? C8 Li1 C7 C6 -129.8(5) . . . . ? C5 Li1 C7 C6 -29.5(3) . . . . ? B1 Li1 C7 C6 -99.1(4) . . . . ? C4 Li1 C7 C6 -63.1(3) . . . . ? N2 Li1 C7 C8 167.7(8) . . . . ? N1 Li1 C7 C8 -89.8(4) . . . . ? C6 Li1 C7 C8 129.8(5) . . . . ? C5 Li1 C7 C8 100.4(4) . . . . ? B1 Li1 C7 C8 30.7(3) . . . . ? C4 Li1 C7 C8 66.7(3) . . . . ? C6 C7 C8 B1 -0.6(7) . . . . ? Li1 C7 C8 B1 -61.0(5) . . . . ? C6 C7 C8 Li1 60.4(5) . . . . ? C4 B1 C8 C7 0.0(7) . . . . ? P1 B1 C8 C7 -179.1(4) . . . . ? Li1 B1 C8 C7 58.2(5) . . . . ? C4 B1 C8 Li1 -58.3(4) . . . . ? P1 B1 C8 Li1 122.7(4) . . . . ? N2 Li1 C8 C7 -62(3) . . . . ? N1 Li1 C8 C7 97.5(4) . . . . ? C6 Li1 C8 C7 -29.4(3) . . . . ? C5 Li1 C8 C7 -64.3(3) . . . . ? B1 Li1 C8 C7 -128.7(5) . . . . ? C4 Li1 C8 C7 -98.8(4) . . . . ? N2 Li1 C8 B1 66(3) . . . . ? N1 Li1 C8 B1 -133.8(4) . . . . ? C7 Li1 C8 B1 128.7(5) . . . . ? C6 Li1 C8 B1 99.3(4) . . . . ? C5 Li1 C8 B1 64.3(3) . . . . ? C4 Li1 C8 B1 29.9(3) . . . . ? C8 B1 P1 C12 19.7(5) . . . . ? C4 B1 P1 C12 -159.3(4) . . . . ? Li1 B1 P1 C12 105.0(4) . . . . ? C8 B1 P1 C9 -75.3(4) . . . . ? C4 B1 P1 C9 105.7(4) . . . . ? Li1 B1 P1 C9 10.0(5) . . . . ? C12 P1 C9 C10 5.5(4) . . . . ? B1 P1 C9 C10 111.1(4) . . . . ? C12 P1 C9 C13 179.9(4) . . . . ? B1 P1 C9 C13 -74.5(4) . . . . ? C13 C9 C10 C11 -178.8(4) . . . . ? P1 C9 C10 C11 -4.6(5) . . . . ? C13 C9 C10 C14 0.1(8) . . . . ? P1 C9 C10 C14 174.3(4) . . . . ? C9 C10 C11 C12 0.7(6) . . . . ? C14 C10 C11 C12 -178.2(4) . . . . ? C9 C10 C11 C15 -179.2(4) . . . . ? C14 C10 C11 C15 1.9(7) . . . . ? C10 C11 C12 C16 -179.2(4) . . . . ? C15 C11 C12 C16 0.7(8) . . . . ? C10 C11 C12 P1 3.6(5) . . . . ? C15 C11 C12 P1 -176.5(4) . . . . ? C9 P1 C12 C11 -5.2(4) . . . . ? B1 P1 C12 C11 -111.2(4) . . . . ? C9 P1 C12 C16 177.5(4) . . . . ? B1 P1 C12 C16 71.6(4) . . . . ? N2 Li1 N1 C21A -101.5(5) . . . . ? C7 Li1 N1 C21A 116.0(5) . . . . ? C6 Li1 N1 C21A 142.5(5) . . . . ? C8 Li1 N1 C21A 81.5(5) . . . . ? C5 Li1 N1 C21A 143.4(12) . . . . ? B1 Li1 N1 C21A 51.9(7) . . . . ? C4 Li1 N1 C21A 42.6(13) . . . . ? N2 Li1 N1 C20A 16.6(6) . . . . ? C7 Li1 N1 C20A -125.9(5) . . . . ? C6 Li1 N1 C20A -99.4(6) . . . . ? C8 Li1 N1 C20A -160.5(5) . . . . ? C5 Li1 N1 C20A -98.6(13) . . . . ? B1 Li1 N1 C20A 170.0(6) . . . . ? C4 Li1 N1 C20A 160.6(11) . . . . ? N2 Li1 N1 C22B 83.5(16) . . . . ? C7 Li1 N1 C22B -59.0(16) . . . . ? C6 Li1 N1 C22B -32.5(17) . . . . ? C8 Li1 N1 C22B -93.5(16) . . . . ? C5 Li1 N1 C22B -32(2) . . . . ? B1 Li1 N1 C22B -123.1(16) . . . . ? C4 Li1 N1 C22B -132.4(18) . . . . ? N2 Li1 N1 C21B -136.7(14) . . . . ? C7 Li1 N1 C21B 80.8(15) . . . . ? C6 Li1 N1 C21B 107.3(15) . . . . ? C8 Li1 N1 C21B 46.2(15) . . . . ? C5 Li1 N1 C21B 108.1(19) . . . . ? B1 Li1 N1 C21B 16.7(15) . . . . ? C4 Li1 N1 C21B 7.3(19) . . . . ? N2 Li1 N1 C20B -19.0(11) . . . . ? C7 Li1 N1 C20B -161.5(11) . . . . ? C6 Li1 N1 C20B -135.0(11) . . . . ? C8 Li1 N1 C20B 163.9(11) . . . . ? C5 Li1 N1 C20B -134.2(16) . . . . ? B1 Li1 N1 C20B 134.4(11) . . . . ? C4 Li1 N1 C20B 125.0(15) . . . . ? N2 Li1 N1 C22A 134.8(6) . . . . ? C7 Li1 N1 C22A -7.7(7) . . . . ? C6 Li1 N1 C22A 18.8(8) . . . . ? C8 Li1 N1 C22A -42.3(6) . . . . ? C5 Li1 N1 C22A 19.6(15) . . . . ? B1 Li1 N1 C22A -71.8(7) . . . . ? C4 Li1 N1 C22A -81.2(12) . . . . ? N1 Li1 N2 C17A 130.2(8) . . . . ? C7 Li1 N2 C17A -121.9(9) . . . . ? C6 Li1 N2 C17A -100.3(8) . . . . ? C8 Li1 N2 C17A -70(3) . . . . ? C5 Li1 N2 C17A -67.6(8) . . . . ? B1 Li1 N2 C17A -13.3(10) . . . . ? C4 Li1 N2 C17A -35.4(8) . . . . ? N1 Li1 N2 C18A -106.2(6) . . . . ? C7 Li1 N2 C18A 1.6(10) . . . . ? C6 Li1 N2 C18A 23.2(7) . . . . ? C8 Li1 N2 C18A 54(3) . . . . ? C5 Li1 N2 C18A 55.9(6) . . . . ? B1 Li1 N2 C18A 110.3(8) . . . . ? C4 Li1 N2 C18A 88.1(6) . . . . ? N1 Li1 N2 C18B 112(2) . . . . ? C7 Li1 N2 C18B -140(2) . . . . ? C6 Li1 N2 C18B -118(2) . . . . ? C8 Li1 N2 C18B -87(4) . . . . ? C5 Li1 N2 C18B -86(2) . . . . ? B1 Li1 N2 C18B -31(2) . . . . ? C4 Li1 N2 C18B -53(2) . . . . ? N1 Li1 N2 C17B -137.7(18) . . . . ? C7 Li1 N2 C17B -29.9(19) . . . . ? C6 Li1 N2 C17B -8.3(18) . . . . ? C8 Li1 N2 C17B 23(4) . . . . ? C5 Li1 N2 C17B 24.4(18) . . . . ? B1 Li1 N2 C17B 78.8(19) . . . . ? C4 Li1 N2 C17B 56.6(18) . . . . ? N1 Li1 N2 C19B -7(2) . . . . ? C7 Li1 N2 C19B 101(2) . . . . ? C6 Li1 N2 C19B 123(2) . . . . ? C8 Li1 N2 C19B 154(4) . . . . ? C5 Li1 N2 C19B 155(2) . . . . ? B1 Li1 N2 C19B -150(2) . . . . ? C4 Li1 N2 C19B -172(2) . . . . ? N1 Li1 N2 C19A 10.4(7) . . . . ? C7 Li1 N2 C19A 118.3(9) . . . . ? C6 Li1 N2 C19A 139.9(7) . . . . ? C8 Li1 N2 C19A 171(3) . . . . ? C5 Li1 N2 C19A 172.6(7) . . . . ? B1 Li1 N2 C19A -133.1(9) . . . . ? C4 Li1 N2 C19A -155.2(7) . . . . ? C17A N2 C19A C20A -162.5(9) . . . . ? C18A N2 C19A C20A 76.4(9) . . . . ? C18B N2 C19A C20A -146.5(18) . . . . ? C17B N2 C19A C20A 104.9(18) . . . . ? C19B N2 C19A C20A 58(3) . . . . ? Li1 N2 C19A C20A -37.9(10) . . . . ? N2 C19A C20A N1 57.9(12) . . . . ? C21A N1 C20A C19A 76.8(9) . . . . ? C22B N1 C20A C19A -143.5(16) . . . . ? C21B N1 C20A C19A 103(2) . . . . ? C20B N1 C20A C19A 49.8(12) . . . . ? C22A N1 C20A C19A -164.4(8) . . . . ? Li1 N1 C20A C19A -42.2(9) . . . . ? C17A N2 C19B C20B -100(2) . . . . ? C18A N2 C19B C20B 143(3) . . . . ? C18B N2 C19B C20B -81(3) . . . . ? C17B N2 C19B C20B 165(3) . . . . ? C19A N2 C19B C20B -54(2) . . . . ? Li1 N2 C19B C20B 34(3) . . . . ? N2 C19B C20B N1 -56(3) . . . . ? C21A N1 C20B C19B 153(2) . . . . ? C20A N1 C20B C19B -52.4(15) . . . . ? C22B N1 C20B C19B -65(2) . . . . ? C21B N1 C20B C19B 165(2) . . . . ? C22A N1 C20B C19B -102(2) . . . . ? Li1 N1 C20B C19B 43.2(19) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.215 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.045 data_gbc044 _database_code_depnum_ccdc_archive 'CCDC 780141' #TrackingRef '2-Mo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H33 B Li N2 P' _chemical_formula_weight 338.19 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' Li Li -0.0003 0.0001 '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 P2(1)/n 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 8.766(3) _cell_length_b 18.191(7) _cell_length_c 13.428(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.435(6) _cell_angle_gamma 90.00 _cell_volume 2131.6(14) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 820 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 17.82 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.054 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9819 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details 'XPREP (Bruker, 2005a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Bruker Smart APEX II CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19893 _diffrn_reflns_av_R_equivalents 0.1355 _diffrn_reflns_av_sigmaI/netI 0.1013 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 24.24 _reflns_number_total 3440 _reflns_number_gt 1764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 (Bruker, 2005b)' _computing_cell_refinement 'APEX 2 (Bruker, 2005b)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.0443P)^2^+0.7035P] 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 3440 _refine_ls_number_parameters 240 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.1465 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1387 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.092 _refine_ls_shift/su_mean 0.002 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 Li1 Li 0.5497(7) 0.2072(3) 0.3996(4) 0.0470(16) Uani 1 1 d . . . B1 B 0.6789(5) 0.1737(2) 0.5670(3) 0.0396(11) Uani 1 1 d . A . C1 C 0.5631(4) 0.2326(2) 0.5779(2) 0.0447(10) Uani 1 1 d . A . H1 H 0.4723 0.2223 0.6156 0.054 Uiso 1 1 calc R . . C2 C 0.5725(5) 0.2991(2) 0.5274(3) 0.0534(11) Uani 1 1 d . A . H2 H 0.4878 0.3356 0.5302 0.064 Uiso 1 1 calc R . . C3 C 0.6865(5) 0.3132(2) 0.4650(3) 0.0595(12) Uani 1 1 d . A . H3 H 0.6834 0.3597 0.4250 0.071 Uiso 1 1 calc R . . C4 C 0.7967(5) 0.2609(2) 0.4516(3) 0.0594(12) Uani 1 1 d . A . H4 H 0.8693 0.2699 0.3998 0.071 Uiso 1 1 calc R . . C5 C 0.7967(4) 0.1925(2) 0.4966(3) 0.0487(10) Uani 1 1 d . A . H5 H 0.8693 0.1538 0.4772 0.058 Uiso 1 1 calc R . . P1 P 0.67204(11) 0.07670(5) 0.62629(7) 0.0434(3) Uani 1 1 d . . . C6 C 0.8533(4) 0.0546(2) 0.6893(3) 0.0468(10) Uani 1 1 d . A . C7 C 0.8398(5) 0.04180(19) 0.7872(3) 0.0506(10) Uani 1 1 d . . . C8 C 0.6882(5) 0.0553(2) 0.8166(3) 0.0540(11) Uani 1 1 d . A . C9 C 0.5853(4) 0.07859(19) 0.7408(3) 0.0486(10) Uani 1 1 d . A . C10 C 0.9975(4) 0.0455(2) 0.6377(3) 0.0718(13) Uani 1 1 d . . . H10A H 1.0679 0.0123 0.6769 0.108 Uiso 1 1 calc R A . H10B H 1.0466 0.0935 0.6318 0.108 Uiso 1 1 calc R . . H10C H 0.9718 0.0247 0.5709 0.108 Uiso 1 1 calc R . . C11 C 0.9659(5) 0.0118(2) 0.8610(3) 0.0830(15) Uani 1 1 d . A . H11A H 0.9342 -0.0357 0.8867 0.125 Uiso 1 1 calc R . . H11B H 0.9856 0.0464 0.9167 0.125 Uiso 1 1 calc R . . H11C H 1.0596 0.0054 0.8275 0.125 Uiso 1 1 calc R . . C12 C 0.6506(6) 0.0441(2) 0.9238(3) 0.0961(17) Uani 1 1 d . . . H12A H 0.5409 0.0524 0.9278 0.144 Uiso 1 1 calc R A . H12B H 0.7097 0.0789 0.9677 0.144 Uiso 1 1 calc R . . H12C H 0.6769 -0.0063 0.9450 0.144 Uiso 1 1 calc R . . C13 C 0.4200(5) 0.0980(2) 0.7474(3) 0.0785(14) Uani 1 1 d . . . H13A H 0.3807 0.0703 0.8021 0.118 Uiso 1 1 calc R A . H13B H 0.3604 0.0856 0.6842 0.118 Uiso 1 1 calc R . . H13C H 0.4112 0.1508 0.7602 0.118 Uiso 1 1 calc R . . N1 N 0.5806(4) 0.17201(18) 0.2534(2) 0.0548(9) Uani 1 1 d D A . N2 N 0.3183(3) 0.18300(16) 0.3662(2) 0.0471(8) Uani 1 1 d D A . C14A C 0.318(4) 0.168(2) 0.2582(9) 0.0557(18) Uani 0.15 1 d PD A 1 H14A H 0.2215 0.1423 0.2352 0.067 Uiso 0.15 1 calc PR A 1 H14B H 0.3174 0.2158 0.2224 0.067 Uiso 0.15 1 calc PR A 1 C15A C 0.448(2) 0.1242(13) 0.230(2) 0.0570(14) Uani 0.15 1 d PD A 1 H15A H 0.4580 0.0780 0.2688 0.068 Uiso 0.15 1 calc PR A 1 H15B H 0.4351 0.1120 0.1576 0.068 Uiso 0.15 1 calc PR A 1 C16A C 0.283(7) 0.127(3) 0.438(5) 0.071(3) Uani 0.15 1 d PD A 1 H16A H 0.2869 0.1488 0.5048 0.106 Uiso 0.15 1 calc PR A 1 H16B H 0.3581 0.0872 0.4379 0.106 Uiso 0.15 1 calc PR A 1 H16C H 0.1801 0.1075 0.4191 0.106 Uiso 0.15 1 calc PR A 1 C17A C 0.227(9) 0.249(3) 0.377(5) 0.067(2) Uani 0.15 1 d PD A 1 H17A H 0.2223 0.2591 0.4486 0.100 Uiso 0.15 1 calc PR A 1 H17B H 0.1237 0.2413 0.3449 0.100 Uiso 0.15 1 calc PR A 1 H17C H 0.2752 0.2905 0.3460 0.100 Uiso 0.15 1 calc PR A 1 C18A C 0.603(5) 0.2378(16) 0.195(3) 0.093(2) Uani 0.15 1 d PDU A 1 H18A H 0.6905 0.2657 0.2258 0.140 Uiso 0.15 1 calc PR A 1 H18B H 0.5106 0.2684 0.1919 0.140 Uiso 0.15 1 calc PR A 1 H18C H 0.6227 0.2237 0.1266 0.140 Uiso 0.15 1 calc PR A 1 C19A C 0.723(2) 0.1306(16) 0.251(3) 0.0780(18) Uani 0.15 1 d PD A 1 H19A H 0.7153 0.0979 0.1927 0.117 Uiso 0.15 1 calc PR A 1 H19B H 0.7419 0.1014 0.3122 0.117 Uiso 0.15 1 calc PR A 1 H19C H 0.8087 0.1649 0.2462 0.117 Uiso 0.15 1 calc PR A 1 C14B C 0.3145(6) 0.1370(2) 0.2751(3) 0.0557(18) Uani 0.85 1 d PD A 2 H14C H 0.2090 0.1359 0.2415 0.067 Uiso 0.85 1 calc PR A 2 H14D H 0.3442 0.0860 0.2940 0.067 Uiso 0.85 1 calc PR A 2 C15B C 0.4206(5) 0.1663(3) 0.2052(3) 0.0570(14) Uani 0.85 1 d PD A 2 H15C H 0.3850 0.2155 0.1816 0.068 Uiso 0.85 1 calc PR A 2 H15D H 0.4191 0.1336 0.1461 0.068 Uiso 0.85 1 calc PR A 2 C16B C 0.2422(10) 0.1421(5) 0.4418(8) 0.071(3) Uani 0.85 1 d PD A 2 H16D H 0.2960 0.0955 0.4562 0.106 Uiso 0.85 1 calc PR A 2 H16E H 0.1357 0.1321 0.4164 0.106 Uiso 0.85 1 calc PR A 2 H16F H 0.2441 0.1713 0.5032 0.106 Uiso 0.85 1 calc PR A 2 C17B C 0.2388(13) 0.2525(4) 0.3462(6) 0.067(2) Uani 0.85 1 d PD A 2 H17D H 0.2419 0.2813 0.4080 0.100 Uiso 0.85 1 calc PR A 2 H17E H 0.1320 0.2429 0.3212 0.100 Uiso 0.85 1 calc PR A 2 H17F H 0.2891 0.2801 0.2958 0.100 Uiso 0.85 1 calc PR A 2 C18B C 0.6679(7) 0.2188(3) 0.1911(5) 0.093(2) Uani 0.85 1 d PDU A 2 H18D H 0.7737 0.2230 0.2215 0.140 Uiso 0.85 1 calc PR A 2 H18E H 0.6211 0.2677 0.1856 0.140 Uiso 0.85 1 calc PR A 2 H18F H 0.6676 0.1971 0.1243 0.140 Uiso 0.85 1 calc PR A 2 C19B C 0.6502(6) 0.0994(3) 0.2635(4) 0.0780(18) Uani 0.85 1 d PD A 2 H19D H 0.6504 0.0768 0.1973 0.117 Uiso 0.85 1 calc PR A 2 H19E H 0.5912 0.0686 0.3059 0.117 Uiso 0.85 1 calc PR A 2 H19F H 0.7557 0.1040 0.2942 0.117 Uiso 0.85 1 calc PR A 2 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 Li1 0.051(4) 0.044(4) 0.044(4) 0.000(3) -0.006(3) 0.003(3) B1 0.043(3) 0.042(3) 0.031(2) 0.000(2) -0.011(2) 0.004(2) C1 0.051(2) 0.049(3) 0.033(2) -0.0046(19) -0.0024(18) -0.001(2) C2 0.062(3) 0.043(3) 0.052(3) -0.006(2) -0.012(2) 0.007(2) C3 0.068(3) 0.048(3) 0.058(3) 0.008(2) -0.017(2) -0.009(2) C4 0.054(3) 0.071(3) 0.052(3) 0.015(2) -0.004(2) -0.012(2) C5 0.043(2) 0.057(3) 0.045(2) 0.007(2) -0.0015(19) 0.004(2) P1 0.0446(6) 0.0453(6) 0.0393(6) 0.0009(5) -0.0020(4) 0.0054(5) C6 0.042(2) 0.045(2) 0.052(2) 0.000(2) -0.0056(19) 0.0046(19) C7 0.067(3) 0.038(2) 0.043(2) 0.001(2) -0.011(2) -0.009(2) C8 0.090(3) 0.037(2) 0.037(2) -0.0015(19) 0.012(2) -0.009(2) C9 0.054(3) 0.034(2) 0.060(3) 0.000(2) 0.021(2) -0.002(2) C10 0.047(3) 0.081(3) 0.086(3) 0.021(3) 0.002(2) 0.017(2) C11 0.108(4) 0.067(3) 0.063(3) 0.020(3) -0.046(3) -0.017(3) C12 0.166(5) 0.077(4) 0.049(3) 0.001(3) 0.033(3) -0.030(3) C13 0.074(3) 0.063(3) 0.103(4) 0.005(3) 0.037(3) 0.005(2) N1 0.058(2) 0.059(2) 0.049(2) 0.0008(18) 0.0124(18) -0.0077(19) N2 0.0424(19) 0.051(2) 0.0471(19) -0.0073(18) -0.0008(15) 0.0049(17) C14A 0.045(3) 0.058(4) 0.062(3) -0.012(3) -0.011(2) -0.001(3) C15A 0.080(4) 0.050(4) 0.041(3) -0.007(3) 0.001(3) -0.005(3) C16A 0.056(6) 0.076(5) 0.082(4) 0.002(4) 0.014(4) -0.006(4) C17A 0.068(4) 0.069(4) 0.061(7) -0.003(4) -0.005(5) 0.022(3) C18A 0.104(5) 0.110(4) 0.071(3) -0.004(3) 0.037(4) -0.030(4) C19A 0.078(4) 0.068(5) 0.088(4) -0.018(4) 0.010(4) 0.009(3) C14B 0.045(3) 0.058(4) 0.062(3) -0.012(3) -0.011(2) -0.001(3) C15B 0.080(4) 0.050(4) 0.041(3) -0.007(3) 0.001(3) -0.005(3) C16B 0.056(6) 0.076(5) 0.082(4) 0.002(4) 0.014(4) -0.006(4) C17B 0.068(4) 0.069(4) 0.061(7) -0.003(4) -0.005(5) 0.022(3) C18B 0.104(5) 0.110(4) 0.071(3) -0.004(3) 0.037(4) -0.030(4) C19B 0.078(4) 0.068(5) 0.088(4) -0.018(4) 0.010(4) 0.009(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Li1 N2 2.083(7) . ? Li1 N1 2.106(7) . ? Li1 C2 2.390(7) . ? Li1 C3 2.393(7) . ? Li1 C4 2.418(7) . ? Li1 C1 2.430(7) . ? Li1 C5 2.434(7) . ? Li1 B1 2.495(7) . ? Li1 C14A 2.74(3) . ? B1 C1 1.493(5) . ? B1 C5 1.505(5) . ? B1 P1 1.939(4) . ? C1 C2 1.392(5) . ? C1 H1 1.0000 . ? C2 C3 1.388(5) . ? C2 H2 1.0000 . ? C3 C4 1.380(5) . ? C3 H3 1.0000 . ? C4 C5 1.383(5) . ? C4 H4 1.0000 . ? C5 H5 1.0000 . ? P1 C6 1.774(4) . ? P1 C9 1.779(4) . ? C6 C7 1.351(5) . ? C6 C10 1.507(5) . ? C7 C8 1.443(5) . ? C7 C11 1.516(5) . ? C8 C9 1.363(5) . ? C8 C12 1.521(5) . ? C9 C13 1.502(5) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N1 C19B 1.455(5) . ? N1 C18A 1.458(10) . ? N1 C18B 1.461(5) . ? N1 C19A 1.464(10) . ? N1 C15A 1.465(10) . ? N1 C15B 1.492(5) . ? N2 C17A 1.454(10) . ? N2 C16A 1.454(10) . ? N2 C17B 1.457(5) . ? N2 C16B 1.469(5) . ? N2 C14A 1.474(10) . ? N2 C14B 1.480(4) . ? C14A C15A 1.472(10) . ? C14A H14A 0.9900 . ? C14A H14B 0.9900 . ? C15A H15A 0.9900 . ? C15A H15B 0.9900 . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C18A H18A 0.9800 . ? C18A H18B 0.9800 . ? C18A H18C 0.9800 . ? C19A H19A 0.9800 . ? C19A H19B 0.9800 . ? C19A H19C 0.9800 . ? C14B C15B 1.482(5) . ? C14B H14C 0.9900 . ? C14B H14D 0.9900 . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 0.9800 . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C18B H18D 0.9800 . ? C18B H18E 0.9800 . ? C18B H18F 0.9800 . ? C19B H19D 0.9800 . ? C19B H19E 0.9800 . ? C19B H19F 0.9800 . ? 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 N2 Li1 N1 86.8(2) . . ? N2 Li1 C2 108.4(3) . . ? N1 Li1 C2 150.7(3) . . ? N2 Li1 C3 133.9(3) . . ? N1 Li1 C3 118.9(3) . . ? C2 Li1 C3 33.73(15) . . ? N2 Li1 C4 167.2(3) . . ? N1 Li1 C4 101.6(3) . . ? C2 Li1 C4 59.9(2) . . ? C3 Li1 C4 33.33(15) . . ? N2 Li1 C1 102.0(3) . . ? N1 Li1 C1 167.8(3) . . ? C2 Li1 C1 33.56(14) . . ? C3 Li1 C1 60.64(19) . . ? C4 Li1 C1 71.3(2) . . ? N2 Li1 C5 153.0(3) . . ? N1 Li1 C5 106.2(3) . . ? C2 Li1 C5 71.5(2) . . ? C3 Li1 C5 60.18(19) . . ? C4 Li1 C5 33.11(14) . . ? C1 Li1 C5 62.37(18) . . ? N2 Li1 B1 119.5(3) . . ? N1 Li1 B1 132.7(3) . . ? C2 Li1 B1 61.56(19) . . ? C3 Li1 B1 72.4(2) . . ? C4 Li1 B1 61.35(19) . . ? C1 Li1 B1 35.26(14) . . ? C5 Li1 B1 35.52(15) . . ? N2 Li1 C14A 32.1(6) . . ? N1 Li1 C14A 55.1(5) . . ? C2 Li1 C14A 133.2(6) . . ? C3 Li1 C14A 140.9(8) . . ? C4 Li1 C14A 152.9(7) . . ? C1 Li1 C14A 134.0(6) . . ? C5 Li1 C14A 155.0(6) . . ? B1 Li1 C14A 143.6(8) . . ? C1 B1 C5 114.3(3) . . ? C1 B1 P1 124.4(3) . . ? C5 B1 P1 121.0(3) . . ? C1 B1 Li1 70.0(2) . . ? C5 B1 Li1 70.0(2) . . ? P1 B1 Li1 124.3(2) . . ? C2 C1 B1 120.2(3) . . ? C2 C1 Li1 71.6(2) . . ? B1 C1 Li1 74.8(2) . . ? C2 C1 H1 119.7 . . ? B1 C1 H1 119.7 . . ? Li1 C1 H1 119.7 . . ? C3 C2 C1 122.3(4) . . ? C3 C2 Li1 73.3(3) . . ? C1 C2 Li1 74.8(2) . . ? C3 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? Li1 C2 H2 118.7 . . ? C4 C3 C2 120.2(4) . . ? C4 C3 Li1 74.3(3) . . ? C2 C3 Li1 73.0(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? Li1 C3 H3 119.8 . . ? C3 C4 C5 122.3(4) . . ? C3 C4 Li1 72.4(3) . . ? C5 C4 Li1 74.1(3) . . ? C3 C4 H4 118.5 . . ? C5 C4 H4 118.5 . . ? Li1 C4 H4 118.5 . . ? C4 C5 B1 120.5(4) . . ? C4 C5 Li1 72.8(3) . . ? B1 C5 Li1 74.5(2) . . ? C4 C5 H5 119.6 . . ? B1 C5 H5 119.6 . . ? Li1 C5 H5 119.6 . . ? C6 P1 C9 91.68(18) . . ? C6 P1 B1 109.93(18) . . ? C9 P1 B1 111.69(18) . . ? C7 C6 C10 125.7(3) . . ? C7 C6 P1 110.2(3) . . ? C10 C6 P1 123.9(3) . . ? C6 C7 C8 113.9(3) . . ? C6 C7 C11 124.9(4) . . ? C8 C7 C11 121.1(4) . . ? C9 C8 C7 114.2(3) . . ? C9 C8 C12 124.1(4) . . ? C7 C8 C12 121.6(4) . . ? C8 C9 C13 127.1(4) . . ? C8 C9 P1 109.4(3) . . ? C13 C9 P1 123.3(3) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19B N1 C18A 136.0(18) . . ? C19B N1 C18B 110.1(4) . . ? C18A N1 C18B 26.6(18) . . ? C19B N1 C19A 35.3(13) . . ? C18A N1 C19A 105(2) . . ? C18B N1 C19A 77.9(14) . . ? C19B N1 C15A 78.4(11) . . ? C18A N1 C15A 121(2) . . ? C18B N1 C15A 132.2(13) . . ? C19A N1 C15A 110.7(17) . . ? C19B N1 C15B 110.2(4) . . ? C18A N1 C15B 90(2) . . ? C18B N1 C15B 108.3(4) . . ? C19A N1 C15B 136.5(14) . . ? C15A N1 C15B 33.8(11) . . ? C19B N1 Li1 106.2(3) . . ? C18A N1 Li1 107(2) . . ? C18B N1 Li1 118.5(4) . . ? C19A N1 Li1 111.3(15) . . ? C15A N1 Li1 102.3(11) . . ? C15B N1 Li1 103.2(3) . . ? C17A N2 C16A 111(4) . . ? C17A N2 C17B 18(3) . . ? C16A N2 C17B 127(2) . . ? C17A N2 C16B 93(3) . . ? C16A N2 C16B 18(3) . . ? C17B N2 C16B 109.1(5) . . ? C17A N2 C14A 107(3) . . ? C16A N2 C14A 123(4) . . ? C17B N2 C14A 91.1(12) . . ? C16B N2 C14A 128.9(18) . . ? C17A N2 C14B 126(3) . . ? C16A N2 C14B 99(3) . . ? C17B N2 C14B 111.5(5) . . ? C16B N2 C14B 108.0(6) . . ? C14A N2 C14B 24.0(15) . . ? C17A N2 Li1 110(4) . . ? C16A N2 Li1 106(3) . . ? C17B N2 Li1 107.2(6) . . ? C16B N2 Li1 117.1(5) . . ? C14A N2 Li1 99.4(15) . . ? C14B N2 Li1 104.1(3) . . ? C15A C14A N2 115(2) . . ? C15A C14A Li1 77.3(16) . . ? N2 C14A Li1 48.6(10) . . ? C15A C14A H14A 108.5 . . ? N2 C14A H14A 108.5 . . ? Li1 C14A H14A 153.4 . . ? C15A C14A H14B 108.5 . . ? N2 C14A H14B 108.5 . . ? Li1 C14A H14B 94.5 . . ? H14A C14A H14B 107.5 . . ? N1 C15A C14A 104(2) . . ? N1 C15A H15A 111.0 . . ? C14A C15A H15A 111.0 . . ? N1 C15A H15B 111.0 . . ? C14A C15A H15B 111.0 . . ? H15A C15A H15B 109.0 . . ? N2 C16A H16A 109.5 . . ? N2 C16A H16B 109.5 . . ? H16A C16A H16B 109.5 . . ? N2 C16A H16C 109.5 . . ? H16A C16A H16C 109.5 . . ? H16B C16A H16C 109.5 . . ? N2 C17A H17A 109.5 . . ? N2 C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? N2 C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? N1 C18A H18A 109.5 . . ? N1 C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? N1 C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? N1 C19A H19A 109.5 . . ? N1 C19A H19B 109.5 . . ? H19A C19A H19B 109.5 . . ? N1 C19A H19C 109.5 . . ? H19A C19A H19C 109.5 . . ? H19B C19A H19C 109.5 . . ? N2 C14B C15B 110.7(4) . . ? N2 C14B H14C 109.5 . . ? C15B C14B H14C 109.5 . . ? N2 C14B H14D 109.5 . . ? C15B C14B H14D 109.5 . . ? H14C C14B H14D 108.1 . . ? C14B C15B N1 111.7(4) . . ? C14B C15B H15C 109.3 . . ? N1 C15B H15C 109.3 . . ? C14B C15B H15D 109.3 . . ? N1 C15B H15D 109.3 . . ? H15C C15B H15D 107.9 . . ? N2 C16B H16D 109.5 . . ? N2 C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? N2 C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? N2 C17B H17D 109.5 . . ? N2 C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? N2 C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? N1 C18B H18D 109.5 . . ? N1 C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? N1 C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? N1 C19B H19D 109.5 . . ? N1 C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? N1 C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? 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 N2 Li1 B1 C1 -67.3(3) . . . . ? N1 Li1 B1 C1 177.1(4) . . . . ? C2 Li1 B1 C1 28.9(2) . . . . ? C3 Li1 B1 C1 63.8(2) . . . . ? C4 Li1 B1 C1 98.1(3) . . . . ? C5 Li1 B1 C1 126.8(3) . . . . ? C14A Li1 B1 C1 -96.4(9) . . . . ? N2 Li1 B1 C5 165.9(4) . . . . ? N1 Li1 B1 C5 50.3(4) . . . . ? C2 Li1 B1 C5 -97.9(3) . . . . ? C3 Li1 B1 C5 -63.0(2) . . . . ? C4 Li1 B1 C5 -28.7(2) . . . . ? C1 Li1 B1 C5 -126.8(3) . . . . ? C14A Li1 B1 C5 136.8(9) . . . . ? N2 Li1 B1 P1 51.4(4) . . . . ? N1 Li1 B1 P1 -64.2(5) . . . . ? C2 Li1 B1 P1 147.6(3) . . . . ? C3 Li1 B1 P1 -177.6(3) . . . . ? C4 Li1 B1 P1 -143.2(3) . . . . ? C1 Li1 B1 P1 118.7(4) . . . . ? C5 Li1 B1 P1 -114.5(4) . . . . ? C14A Li1 B1 P1 22.3(10) . . . . ? C5 B1 C1 C2 -1.9(5) . . . . ? P1 B1 C1 C2 -176.0(3) . . . . ? Li1 B1 C1 C2 -57.5(3) . . . . ? C5 B1 C1 Li1 55.7(3) . . . . ? P1 B1 C1 Li1 -118.5(3) . . . . ? N2 Li1 C1 C2 -105.4(3) . . . . ? N1 Li1 C1 C2 119.7(15) . . . . ? C3 Li1 C1 C2 28.6(2) . . . . ? C4 Li1 C1 C2 63.3(3) . . . . ? C5 Li1 C1 C2 98.1(3) . . . . ? B1 Li1 C1 C2 129.8(3) . . . . ? C14A Li1 C1 C2 -105.4(11) . . . . ? N2 Li1 C1 B1 124.8(3) . . . . ? N1 Li1 C1 B1 -10.1(15) . . . . ? C2 Li1 C1 B1 -129.8(3) . . . . ? C3 Li1 C1 B1 -101.2(3) . . . . ? C4 Li1 C1 B1 -66.5(2) . . . . ? C5 Li1 C1 B1 -31.7(2) . . . . ? C14A Li1 C1 B1 124.8(11) . . . . ? B1 C1 C2 C3 0.8(5) . . . . ? Li1 C1 C2 C3 -58.3(4) . . . . ? B1 C1 C2 Li1 59.1(3) . . . . ? N2 Li1 C2 C3 -144.8(3) . . . . ? N1 Li1 C2 C3 -26.6(7) . . . . ? C4 Li1 C2 C3 29.5(2) . . . . ? C1 Li1 C2 C3 131.3(4) . . . . ? C5 Li1 C2 C3 63.7(3) . . . . ? B1 Li1 C2 C3 101.0(3) . . . . ? C14A Li1 C2 C3 -120.6(11) . . . . ? N2 Li1 C2 C1 83.9(3) . . . . ? N1 Li1 C2 C1 -157.9(6) . . . . ? C3 Li1 C2 C1 -131.3(4) . . . . ? C4 Li1 C2 C1 -101.9(3) . . . . ? C5 Li1 C2 C1 -67.7(2) . . . . ? B1 Li1 C2 C1 -30.3(2) . . . . ? C14A Li1 C2 C1 108.0(11) . . . . ? C1 C2 C3 C4 -0.6(6) . . . . ? Li1 C2 C3 C4 -59.6(4) . . . . ? C1 C2 C3 Li1 59.1(3) . . . . ? N2 Li1 C3 C4 178.6(4) . . . . ? N1 Li1 C3 C4 -65.2(4) . . . . ? C2 Li1 C3 C4 129.2(4) . . . . ? C1 Li1 C3 C4 100.8(3) . . . . ? C5 Li1 C3 C4 27.7(2) . . . . ? B1 Li1 C3 C4 64.3(3) . . . . ? C14A Li1 C3 C4 -134.3(10) . . . . ? N2 Li1 C3 C2 49.4(4) . . . . ? N1 Li1 C3 C2 165.5(4) . . . . ? C4 Li1 C3 C2 -129.2(4) . . . . ? C1 Li1 C3 C2 -28.4(2) . . . . ? C5 Li1 C3 C2 -101.5(3) . . . . ? B1 Li1 C3 C2 -64.9(3) . . . . ? C14A Li1 C3 C2 96.5(9) . . . . ? C2 C3 C4 C5 1.8(6) . . . . ? Li1 C3 C4 C5 -57.2(4) . . . . ? C2 C3 C4 Li1 59.0(4) . . . . ? N2 Li1 C4 C3 -4.4(15) . . . . ? N1 Li1 C4 C3 125.7(3) . . . . ? C2 Li1 C4 C3 -29.8(2) . . . . ? C1 Li1 C4 C3 -64.6(3) . . . . ? C5 Li1 C4 C3 -132.4(4) . . . . ? B1 Li1 C4 C3 -101.7(3) . . . . ? C14A Li1 C4 C3 97.3(15) . . . . ? N2 Li1 C4 C5 128.0(15) . . . . ? N1 Li1 C4 C5 -101.9(3) . . . . ? C2 Li1 C4 C5 102.6(3) . . . . ? C3 Li1 C4 C5 132.4(4) . . . . ? C1 Li1 C4 C5 67.8(3) . . . . ? B1 Li1 C4 C5 30.7(2) . . . . ? C14A Li1 C4 C5 -130.2(15) . . . . ? C3 C4 C5 B1 -3.1(6) . . . . ? Li1 C4 C5 B1 -59.5(3) . . . . ? C3 C4 C5 Li1 56.4(4) . . . . ? C1 B1 C5 C4 3.0(5) . . . . ? P1 B1 C5 C4 177.4(3) . . . . ? Li1 B1 C5 C4 58.7(3) . . . . ? C1 B1 C5 Li1 -55.7(3) . . . . ? P1 B1 C5 Li1 118.7(3) . . . . ? N2 Li1 C5 C4 -157.4(7) . . . . ? N1 Li1 C5 C4 86.5(3) . . . . ? C2 Li1 C5 C4 -62.9(3) . . . . ? C3 Li1 C5 C4 -27.9(2) . . . . ? C1 Li1 C5 C4 -98.1(3) . . . . ? B1 Li1 C5 C4 -129.6(4) . . . . ? C14A Li1 C5 C4 124.6(19) . . . . ? N2 Li1 C5 B1 -27.8(7) . . . . ? N1 Li1 C5 B1 -143.9(3) . . . . ? C2 Li1 C5 B1 66.7(2) . . . . ? C3 Li1 C5 B1 101.7(3) . . . . ? C4 Li1 C5 B1 129.6(4) . . . . ? C1 Li1 C5 B1 31.4(2) . . . . ? C14A Li1 C5 B1 -105.8(18) . . . . ? C1 B1 P1 C6 -131.1(3) . . . . ? C5 B1 P1 C6 55.1(3) . . . . ? Li1 B1 P1 C6 140.9(3) . . . . ? C1 B1 P1 C9 -30.9(4) . . . . ? C5 B1 P1 C9 155.3(3) . . . . ? Li1 B1 P1 C9 -118.9(3) . . . . ? C9 P1 C6 C7 6.6(3) . . . . ? B1 P1 C6 C7 120.5(3) . . . . ? C9 P1 C6 C10 -178.1(3) . . . . ? B1 P1 C6 C10 -64.2(4) . . . . ? C10 C6 C7 C8 179.8(3) . . . . ? P1 C6 C7 C8 -5.0(4) . . . . ? C10 C6 C7 C11 -3.7(6) . . . . ? P1 C6 C7 C11 171.6(3) . . . . ? C6 C7 C8 C9 -0.1(5) . . . . ? C11 C7 C8 C9 -176.8(3) . . . . ? C6 C7 C8 C12 -179.9(4) . . . . ? C11 C7 C8 C12 3.4(5) . . . . ? C7 C8 C9 C13 -179.2(3) . . . . ? C12 C8 C9 C13 0.6(6) . . . . ? C7 C8 C9 P1 5.1(4) . . . . ? C12 C8 C9 P1 -175.1(3) . . . . ? C6 P1 C9 C8 -6.6(3) . . . . ? B1 P1 C9 C8 -118.8(3) . . . . ? C6 P1 C9 C13 177.5(3) . . . . ? B1 P1 C9 C13 65.2(3) . . . . ? N2 Li1 N1 C19B -104.2(3) . . . . ? C2 Li1 N1 C19B 132.6(6) . . . . ? C3 Li1 N1 C19B 116.2(4) . . . . ? C4 Li1 N1 C19B 85.6(3) . . . . ? C1 Li1 N1 C19B 31.9(16) . . . . ? C5 Li1 N1 C19B 51.7(4) . . . . ? B1 Li1 N1 C19B 24.0(5) . . . . ? C14A Li1 N1 C19B -109.7(10) . . . . ? N2 Li1 N1 C18A 105(2) . . . . ? C2 Li1 N1 C18A -18(2) . . . . ? C3 Li1 N1 C18A -34(2) . . . . ? C4 Li1 N1 C18A -65(2) . . . . ? C1 Li1 N1 C18A -119(2) . . . . ? C5 Li1 N1 C18A -99(2) . . . . ? B1 Li1 N1 C18A -127(2) . . . . ? C14A Li1 N1 C18A 100(2) . . . . ? N2 Li1 N1 C18B 131.4(4) . . . . ? C2 Li1 N1 C18B 8.2(8) . . . . ? C3 Li1 N1 C18B -8.3(5) . . . . ? C4 Li1 N1 C18B -38.9(5) . . . . ? C1 Li1 N1 C18B -92.5(16) . . . . ? C5 Li1 N1 C18B -72.7(4) . . . . ? B1 Li1 N1 C18B -100.5(5) . . . . ? C14A Li1 N1 C18B 125.8(10) . . . . ? N2 Li1 N1 C19A -141.2(15) . . . . ? C2 Li1 N1 C19A 95.7(16) . . . . ? C3 Li1 N1 C19A 79.2(15) . . . . ? C4 Li1 N1 C19A 48.6(15) . . . . ? C1 Li1 N1 C19A -5(2) . . . . ? C5 Li1 N1 C19A 14.8(15) . . . . ? B1 Li1 N1 C19A -13.0(16) . . . . ? C14A Li1 N1 C19A -146.7(18) . . . . ? N2 Li1 N1 C15A -22.9(12) . . . . ? C2 Li1 N1 C15A -146.0(13) . . . . ? C3 Li1 N1 C15A -162.5(12) . . . . ? C4 Li1 N1 C15A 166.9(12) . . . . ? C1 Li1 N1 C15A 113.3(19) . . . . ? C5 Li1 N1 C15A 133.1(12) . . . . ? B1 Li1 N1 C15A 105.3(12) . . . . ? C14A Li1 N1 C15A -28.4(14) . . . . ? N2 Li1 N1 C15B 11.7(3) . . . . ? C2 Li1 N1 C15B -111.4(6) . . . . ? C3 Li1 N1 C15B -127.9(3) . . . . ? C4 Li1 N1 C15B -158.5(3) . . . . ? C1 Li1 N1 C15B 147.9(15) . . . . ? C5 Li1 N1 C15B 167.7(3) . . . . ? B1 Li1 N1 C15B 139.9(4) . . . . ? C14A Li1 N1 C15B 6.2(10) . . . . ? N1 Li1 N2 C17A -121(3) . . . . ? C2 Li1 N2 C17A 33(3) . . . . ? C3 Li1 N2 C17A 7(3) . . . . ? C4 Li1 N2 C17A 10(3) . . . . ? C1 Li1 N2 C17A 68(3) . . . . ? C5 Li1 N2 C17A 119(3) . . . . ? B1 Li1 N2 C17A 101(3) . . . . ? C14A Li1 N2 C17A -112(3) . . . . ? N1 Li1 N2 C16A 119(3) . . . . ? C2 Li1 N2 C16A -86(3) . . . . ? C3 Li1 N2 C16A -112(3) . . . . ? C4 Li1 N2 C16A -109(3) . . . . ? C1 Li1 N2 C16A -52(3) . . . . ? C5 Li1 N2 C16A -1(3) . . . . ? B1 Li1 N2 C16A -19(3) . . . . ? C14A Li1 N2 C16A 128(3) . . . . ? N1 Li1 N2 C17B -102.7(4) . . . . ? C2 Li1 N2 C17B 51.7(4) . . . . ? C3 Li1 N2 C17B 25.3(5) . . . . ? C4 Li1 N2 C17B 28.7(15) . . . . ? C1 Li1 N2 C17B 85.9(4) . . . . ? C5 Li1 N2 C17B 137.0(7) . . . . ? B1 Li1 N2 C17B 118.9(4) . . . . ? C14A Li1 N2 C17B -94.1(14) . . . . ? N1 Li1 N2 C16B 134.4(5) . . . . ? C2 Li1 N2 C16B -71.1(5) . . . . ? C3 Li1 N2 C16B -97.5(6) . . . . ? C4 Li1 N2 C16B -94.1(15) . . . . ? C1 Li1 N2 C16B -36.9(5) . . . . ? C5 Li1 N2 C16B 14.2(9) . . . . ? B1 Li1 N2 C16B -4.0(6) . . . . ? C14A Li1 N2 C16B 143.0(15) . . . . ? N1 Li1 N2 C14A -8.6(14) . . . . ? C2 Li1 N2 C14A 145.8(14) . . . . ? C3 Li1 N2 C14A 119.5(14) . . . . ? C4 Li1 N2 C14A 123(2) . . . . ? C1 Li1 N2 C14A -180.0(14) . . . . ? C5 Li1 N2 C14A -128.9(15) . . . . ? B1 Li1 N2 C14A -147.0(14) . . . . ? N1 Li1 N2 C14B 15.4(3) . . . . ? C2 Li1 N2 C14B 169.9(3) . . . . ? C3 Li1 N2 C14B 143.5(4) . . . . ? C4 Li1 N2 C14B 146.9(14) . . . . ? C1 Li1 N2 C14B -155.9(3) . . . . ? C5 Li1 N2 C14B -104.8(7) . . . . ? B1 Li1 N2 C14B -123.0(3) . . . . ? C14A Li1 N2 C14B 24.0(14) . . . . ? C17A N2 C14A C15A 157(4) . . . . ? C16A N2 C14A C15A -73(4) . . . . ? C17B N2 C14A C15A 150(3) . . . . ? C16B N2 C14A C15A -94(3) . . . . ? C14B N2 C14A C15A -61(2) . . . . ? Li1 N2 C14A C15A 42(3) . . . . ? C17A N2 C14A Li1 114(4) . . . . ? C16A N2 C14A Li1 -116(3) . . . . ? C17B N2 C14A Li1 107.6(6) . . . . ? C16B N2 C14A Li1 -136.5(11) . . . . ? C14B N2 C14A Li1 -104(3) . . . . ? N2 Li1 C14A C15A -141(3) . . . . ? N1 Li1 C14A C15A 28.3(14) . . . . ? C2 Li1 C14A C15A 171.8(13) . . . . ? C3 Li1 C14A C15A 122.6(15) . . . . ? C4 Li1 C14A C15A 63(3) . . . . ? C1 Li1 C14A C15A -141.2(14) . . . . ? C5 Li1 C14A C15A -18(3) . . . . ? B1 Li1 C14A C15A -88.2(19) . . . . ? N1 Li1 C14A N2 169.5(17) . . . . ? C2 Li1 C14A N2 -47.0(18) . . . . ? C3 Li1 C14A N2 -96.2(15) . . . . ? C4 Li1 C14A N2 -155.9(8) . . . . ? C1 Li1 C14A N2 0.0(19) . . . . ? C5 Li1 C14A N2 123.3(12) . . . . ? B1 Li1 C14A N2 53.0(16) . . . . ? C19B N1 C15A C14A 153(2) . . . . ? C18A N1 C15A C14A -70(3) . . . . ? C18B N1 C15A C14A -101(2) . . . . ? C19A N1 C15A C14A 167(2) . . . . ? C15B N1 C15A C14A -46.9(12) . . . . ? Li1 N1 C15A C14A 48(2) . . . . ? N2 C14A C15A N1 -66(3) . . . . ? Li1 C14A C15A N1 -35.2(15) . . . . ? C17A N2 C14B C15B 86(4) . . . . ? C16A N2 C14B C15B -150(3) . . . . ? C17B N2 C14B C15B 73.9(7) . . . . ? C16B N2 C14B C15B -166.3(5) . . . . ? C14A N2 C14B C15B 40(3) . . . . ? Li1 N2 C14B C15B -41.2(5) . . . . ? N2 C14B C15B N1 56.8(6) . . . . ? C19B N1 C15B C14B 74.7(5) . . . . ? C18A N1 C15B C14B -146(2) . . . . ? C18B N1 C15B C14B -164.8(4) . . . . ? C19A N1 C15B C14B 104(2) . . . . ? C15A N1 C15B C14B 54(2) . . . . ? Li1 N1 C15B C14B -38.4(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.24 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.183 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.044