# 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 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_address ; Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan ; #===END loop_ _publ_author_name 'Shi Tang' 'Masahide Takeda' 'Yoshiaki Nakao' 'Tamejiro Hiyama' _publ_contact_author 'Yoshiaki Nakao' _publ_contact_author_email 'yoshiakinakao@npc05.mbox.media.kyoto-u.ac.jp ' _publ_contact_author_fax +81-75-383-2445 _publ_contact_author_phone +81-75-383-2443 _publ_section_title ; Nickel-catalysed Cross-coupling Reaction of Aryl(triorgano)silanes with Aryl Chlorides and Tosylates ; data_1'a_dinitrobenzoate _database_code_depnum_ccdc_archive 'CCDC 779621' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 N2 O6 Si' _chemical_formula_weight 442.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.895(5) _cell_length_b 9.843(6) _cell_length_c 14.780(9) _cell_angle_alpha 86.269(10) _cell_angle_beta 88.770(11) _cell_angle_gamma 83.748(12) _cell_volume 1139.1(12) _cell_formula_units_Z 2 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 2742 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 26.13 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9320 _exptl_absorpt_correction_T_max 0.9584 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK(J\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6185 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4158 _reflns_number_gt 3438 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[(J\s^2^(Fo^2^)+(0.0741P)^2^+0.1297P] 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 4158 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1311 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 Si1 Si 1.17521(6) -0.09098(5) 0.29700(3) 0.05197(17) Uani 1 1 d . . . O6 O 0.74238(15) -0.06654(12) 0.20340(7) 0.0543(3) Uani 1 1 d . . . C6 C 0.5764(2) 0.18123(18) 0.24042(11) 0.0516(4) Uani 1 1 d . . . H6 H 0.6312 0.1272 0.2873 0.062 Uiso 1 1 calc R . . C17 C 1.0964(2) 0.07719(17) 0.23565(11) 0.0506(4) Uani 1 1 d . . . C9 C 0.8995(2) -0.26275(17) 0.27952(11) 0.0495(4) Uani 1 1 d . . . H9 H 0.9834 -0.3408 0.2678 0.059 Uiso 1 1 calc R . . C14 C 0.9841(2) -0.17435(16) 0.34463(11) 0.0481(4) Uani 1 1 d . . . H14 H 0.8975 -0.0993 0.3587 0.058 Uiso 1 1 calc R . . C10 C 0.7450(2) -0.32181(19) 0.32381(13) 0.0596(5) Uani 1 1 d . . . H10A H 0.6561 -0.2476 0.3328 0.072 Uiso 1 1 calc R . . H10B H 0.7018 -0.3827 0.2830 0.072 Uiso 1 1 calc R . . O5 O 0.7068(2) -0.02906(16) 0.05343(9) 0.0778(4) Uani 1 1 d . . . C7 C 0.6838(2) 0.00627(19) 0.12961(12) 0.0538(4) Uani 1 1 d . . . C5 C 0.5855(2) 0.13855(18) 0.15254(11) 0.0510(4) Uani 1 1 d . . . C8 C 0.8539(2) -0.19146(18) 0.18828(12) 0.0551(4) Uani 1 1 d . . . H8A H 0.9563 -0.1692 0.1558 0.066 Uiso 1 1 calc R . . H8B H 0.7962 -0.2509 0.1523 0.066 Uiso 1 1 calc R . . C4 C 0.5041(2) 0.22078(19) 0.08301(13) 0.0593(5) Uani 1 1 d . . . H4 H 0.5098 0.1939 0.0237 0.071 Uiso 1 1 calc R . . C1 C 0.4846(2) 0.30510(18) 0.25742(12) 0.0555(4) Uani 1 1 d . . . N1 N 0.4766(2) 0.35109(18) 0.35052(12) 0.0703(5) Uani 1 1 d . . . C3 C 0.4147(2) 0.34299(19) 0.10398(13) 0.0609(5) Uani 1 1 d . . . C2 C 0.4012(2) 0.38763(19) 0.19018(14) 0.0609(5) Uani 1 1 d . . . H2 H 0.3384 0.4700 0.2025 0.073 Uiso 1 1 calc R . . N2 N 0.3273(3) 0.43129(19) 0.03080(15) 0.0813(6) Uani 1 1 d . . . C13 C 1.0228(3) -0.2585(2) 0.43508(12) 0.0603(5) Uani 1 1 d . . . H13A H 1.1081 -0.3346 0.4244 0.072 Uiso 1 1 calc R . . H13B H 1.0698 -0.2012 0.4770 0.072 Uiso 1 1 calc R . . C18 C 1.0938(3) 0.0983(2) 0.14187(12) 0.0625(5) Uani 1 1 d . . . H18 H 1.1399 0.0285 0.1064 0.075 Uiso 1 1 calc R . . O3 O 0.2368(3) 0.53391(19) 0.05220(14) 0.1131(7) Uani 1 1 d . . . O4 O 0.3521(3) 0.39817(18) -0.04713(13) 0.1052(6) Uani 1 1 d . . . C22 C 1.0288(3) 0.18677(19) 0.28505(13) 0.0621(5) Uani 1 1 d . . . H22 H 1.0291 0.1770 0.3481 0.075 Uiso 1 1 calc R . . O2 O 0.3930(2) 0.45990(17) 0.36412(11) 0.0948(5) Uani 1 1 d . . . C12 C 0.8660(3) -0.3131(2) 0.47766(13) 0.0656(5) Uani 1 1 d . . . H12A H 0.7847 -0.2369 0.4936 0.079 Uiso 1 1 calc R . . H12B H 0.8975 -0.3676 0.5330 0.079 Uiso 1 1 calc R . . C15 C 1.3062(3) -0.2040(2) 0.21949(16) 0.0752(6) Uani 1 1 d . . . H15A H 1.4020 -0.1591 0.1969 0.113 Uiso 1 1 calc R . . H15B H 1.2379 -0.2223 0.1696 0.113 Uiso 1 1 calc R . . H15C H 1.3459 -0.2886 0.2521 0.113 Uiso 1 1 calc R . . O1 O 0.5542(3) 0.27943(19) 0.40887(10) 0.1042(6) Uani 1 1 d . . . C21 C 0.9612(3) 0.3100(2) 0.24276(17) 0.0745(6) Uani 1 1 d . . . H21 H 0.9184 0.3817 0.2775 0.089 Uiso 1 1 calc R . . C19 C 1.0239(3) 0.2212(2) 0.09993(14) 0.0760(6) Uani 1 1 d . . . H19 H 1.0223 0.2322 0.0370 0.091 Uiso 1 1 calc R . . C11 C 0.7834(3) -0.3999(2) 0.41415(13) 0.0674(5) Uani 1 1 d . . . H11A H 0.6785 -0.4269 0.4415 0.081 Uiso 1 1 calc R . . H11B H 0.8590 -0.4823 0.4045 0.081 Uiso 1 1 calc R . . C16 C 1.3111(3) -0.0537(2) 0.39270(15) 0.0780(6) Uani 1 1 d . . . H16A H 1.3605 -0.1382 0.4220 0.117 Uiso 1 1 calc R . . H16B H 1.2423 -0.0022 0.4357 0.117 Uiso 1 1 calc R . . H16C H 1.4002 -0.0014 0.3695 0.117 Uiso 1 1 calc R . . C20 C 0.9570(3) 0.3266(2) 0.15060(17) 0.0769(6) Uani 1 1 d . . . H20 H 0.9093 0.4086 0.1223 0.092 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 Si1 0.0498(3) 0.0468(3) 0.0585(3) 0.0001(2) -0.0079(2) -0.0022(2) O6 0.0559(7) 0.0579(7) 0.0466(6) 0.0001(5) -0.0093(5) 0.0044(6) C6 0.0464(9) 0.0564(10) 0.0505(10) 0.0107(8) -0.0055(7) -0.0058(7) C17 0.0508(9) 0.0489(9) 0.0520(10) -0.0009(7) -0.0019(7) -0.0063(7) C9 0.0490(9) 0.0434(9) 0.0548(10) -0.0047(7) -0.0063(7) 0.0032(7) C14 0.0495(9) 0.0430(8) 0.0502(9) -0.0026(7) -0.0060(7) 0.0029(7) C10 0.0559(10) 0.0554(10) 0.0685(12) -0.0043(9) -0.0089(8) -0.0090(8) O5 0.0946(11) 0.0862(10) 0.0494(8) -0.0060(7) -0.0138(7) 0.0077(8) C7 0.0514(9) 0.0639(11) 0.0465(10) 0.0008(8) -0.0096(7) -0.0087(8) C5 0.0461(9) 0.0564(10) 0.0508(10) 0.0061(8) -0.0095(7) -0.0101(7) C8 0.0561(10) 0.0561(10) 0.0528(10) -0.0115(8) -0.0071(8) 0.0015(8) C4 0.0638(11) 0.0614(11) 0.0540(10) 0.0089(8) -0.0180(8) -0.0163(9) C1 0.0549(10) 0.0538(10) 0.0577(11) 0.0053(8) -0.0007(8) -0.0104(8) N1 0.0800(11) 0.0653(11) 0.0635(11) 0.0007(8) 0.0083(9) -0.0041(9) C3 0.0623(11) 0.0529(10) 0.0679(12) 0.0158(9) -0.0239(9) -0.0146(9) C2 0.0582(11) 0.0463(10) 0.0769(13) 0.0078(9) -0.0089(9) -0.0059(8) N2 0.0958(14) 0.0577(11) 0.0908(14) 0.0225(10) -0.0435(11) -0.0184(10) C13 0.0661(11) 0.0613(11) 0.0528(10) 0.0036(8) -0.0122(8) -0.0062(9) C18 0.0692(12) 0.0647(12) 0.0534(10) 0.0016(9) 0.0038(9) -0.0101(9) O3 0.1377(17) 0.0690(11) 0.1255(16) 0.0196(10) -0.0546(13) 0.0164(11) O4 0.1487(17) 0.0853(11) 0.0809(12) 0.0211(9) -0.0565(11) -0.0150(11) C22 0.0731(12) 0.0553(11) 0.0568(11) -0.0026(8) -0.0045(9) -0.0014(9) O2 0.1196(14) 0.0717(10) 0.0883(12) -0.0100(8) 0.0166(10) 0.0103(10) C12 0.0772(13) 0.0642(12) 0.0550(11) 0.0038(9) -0.0019(9) -0.0101(10) C15 0.0563(11) 0.0671(13) 0.1002(16) -0.0109(11) 0.0048(11) 0.0043(10) O1 0.1482(17) 0.0996(12) 0.0566(9) -0.0008(9) -0.0099(10) 0.0232(12) C21 0.0778(14) 0.0511(11) 0.0919(16) -0.0036(10) -0.0031(11) 0.0052(10) C19 0.0828(14) 0.0862(15) 0.0591(12) 0.0203(11) -0.0091(10) -0.0225(12) C11 0.0731(13) 0.0596(11) 0.0700(13) 0.0023(9) 0.0017(10) -0.0141(10) C16 0.0746(13) 0.0767(14) 0.0848(15) 0.0091(11) -0.0286(11) -0.0202(11) C20 0.0690(13) 0.0630(13) 0.0957(17) 0.0235(12) -0.0153(11) -0.0077(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si1 C15 1.866(2) . ? Si1 C16 1.872(2) . ? Si1 C17 1.8851(19) . ? Si1 C14 1.8957(19) . ? O6 C7 1.328(2) . ? O6 C8 1.459(2) . ? C6 C1 1.384(3) . ? C6 C5 1.389(3) . ? C6 H6 0.9300 . ? C17 C18 1.388(3) . ? C17 C22 1.393(3) . ? C9 C8 1.511(2) . ? C9 C10 1.525(3) . ? C9 C14 1.547(2) . ? C9 H9 0.9800 . ? C14 C13 1.544(2) . ? C14 H14 0.9800 . ? C10 C11 1.516(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? O5 C7 1.204(2) . ? C7 C5 1.496(3) . ? C5 C4 1.390(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C4 C3 1.377(3) . ? C4 H4 0.9300 . ? C1 C2 1.374(3) . ? C1 N1 1.474(3) . ? N1 O1 1.211(2) . ? N1 O2 1.221(2) . ? C3 C2 1.373(3) . ? C3 N2 1.477(2) . ? C2 H2 0.9300 . ? N2 O4 1.223(3) . ? N2 O3 1.227(3) . ? C13 C12 1.511(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C18 C19 1.387(3) . ? C18 H18 0.9300 . ? C22 C21 1.386(3) . ? C22 H22 0.9300 . ? C12 C11 1.513(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C21 C20 1.362(3) . ? C21 H21 0.9300 . ? C19 C20 1.371(3) . ? C19 H19 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C20 H20 0.9300 . ? 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 C15 Si1 C16 108.92(12) . . ? C15 Si1 C17 110.75(10) . . ? C16 Si1 C17 107.86(10) . . ? C15 Si1 C14 111.56(10) . . ? C16 Si1 C14 109.22(10) . . ? C17 Si1 C14 108.44(8) . . ? C7 O6 C8 116.21(14) . . ? C1 C6 C5 119.21(16) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C18 C17 C22 116.49(17) . . ? C18 C17 Si1 123.74(14) . . ? C22 C17 Si1 119.71(14) . . ? C8 C9 C10 110.61(14) . . ? C8 C9 C14 114.52(14) . . ? C10 C9 C14 111.48(14) . . ? C8 C9 H9 106.6 . . ? C10 C9 H9 106.6 . . ? C14 C9 H9 106.6 . . ? C13 C14 C9 109.26(14) . . ? C13 C14 Si1 112.51(12) . . ? C9 C14 Si1 115.87(12) . . ? C13 C14 H14 106.2 . . ? C9 C14 H14 106.2 . . ? Si1 C14 H14 106.2 . . ? C11 C10 C9 113.45(15) . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? O5 C7 O6 124.47(18) . . ? O5 C7 C5 123.83(16) . . ? O6 C7 C5 111.70(15) . . ? C6 C5 C4 119.82(18) . . ? C6 C5 C7 121.79(15) . . ? C4 C5 C7 118.38(17) . . ? O6 C8 C9 108.22(14) . . ? O6 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? O6 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? C3 C4 C5 118.39(18) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C2 C1 C6 122.19(18) . . ? C2 C1 N1 118.64(18) . . ? C6 C1 N1 119.17(16) . . ? O1 N1 O2 123.8(2) . . ? O1 N1 C1 118.17(18) . . ? O2 N1 C1 118.00(18) . . ? C2 C3 C4 123.37(17) . . ? C2 C3 N2 117.66(19) . . ? C4 C3 N2 118.97(19) . . ? C3 C2 C1 117.02(18) . . ? C3 C2 H2 121.5 . . ? C1 C2 H2 121.5 . . ? O4 N2 O3 124.47(19) . . ? O4 N2 C3 117.7(2) . . ? O3 N2 C3 117.8(2) . . ? C12 C13 C14 112.42(15) . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? C19 C18 C17 121.5(2) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C21 C22 C17 121.74(19) . . ? C21 C22 H22 119.1 . . ? C17 C22 H22 119.1 . . ? C13 C12 C11 111.63(17) . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? Si1 C15 H15A 109.5 . . ? Si1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Si1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C20 C21 C22 120.4(2) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C20 C19 C18 120.5(2) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C12 C11 C10 110.97(16) . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? Si1 C16 H16A 109.5 . . ? Si1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C21 C20 C19 119.3(2) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.316 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.053