# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jaesook Yun' _publ_contact_author_address ; Department of Molecular Science and Technology Ajou University San 5 Suwon Kyounggi-do 443-749 SOUTH KOREA ; _publ_contact_author_email JAESOOK@AJOU.AC.KR _publ_section_title ; A new alternative to Stryker's reagent in hydrosilylation: synthesis, structure, and reactivity of a well-defined (carbene)copper(II) acetate complex ; loop_ _publ_author_name 'Jaesook Yun.' 'Daesung Kim.' 'Hoseop Yun.' data_l _database_code_depnum_ccdc_archive 'CCDC 274568' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [1,3-bis(diisopropylphenyl)imidazole-2-ylidene]copper(II) acetate ; _chemical_name_common ;(1,3-bis(diisopropylphenyl)imidazole-2-ylidene)copper(ii) acetate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H42 Cu N2 O4' _chemical_formula_weight 570.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.863(3) _cell_length_b 8.680(4) _cell_length_c 17.977(5) _cell_angle_alpha 90.00 _cell_angle_beta 119.275(15) _cell_angle_gamma 90.00 _cell_volume 3111.8(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8100 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description cube _exptl_crystal_colour blue _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1212 _exptl_absorpt_coefficient_mu 0.737 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-axis Rapid' _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 14788 _diffrn_reflns_av_R_equivalents 0.1088 _diffrn_reflns_av_sigmaI/netI 0.0952 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3554 _reflns_number_gt 1667 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'RapidAuto (Rigaku, 2005)' _computing_cell_refinement 'RapidAuto (Rigaku, 2005)' _computing_data_reduction 'RapidAuto (Rigaku, 2005)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'locally modified version of ORTEP-II (Johnson, 1965)' _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; ; _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^)+(0.0568P)^2^+0.1036P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3554 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1533 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1450 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.00154(19) -0.4619(4) 0.28584(18) 0.0543(10) Uani 1 1 d . . . H1 H -0.0026 -0.5480 0.3159 0.065 Uiso 1 1 calc R . . C2 C 0.0000 -0.2141(5) 0.2500 0.0400(11) Uani 1 2 d S . . C3 C -0.00804(19) -0.2619(3) 0.38104(18) 0.0440(8) Uani 1 1 d . . . C4 C 0.0504(2) -0.2576(4) 0.4597(2) 0.0543(10) Uani 1 1 d . . . C5 C 0.0430(2) -0.2229(5) 0.5304(2) 0.0682(12) Uani 1 1 d . . . H5 H 0.0807 -0.2193 0.5843 0.082 Uiso 1 1 calc R . . C6 C -0.01819(19) -0.1942(3) 0.5217(2) 0.0741(13) Uani 1 1 d . . . H6 H -0.0219 -0.1731 0.5700 0.089 Uiso 1 1 calc R . . C7 C -0.07500(19) -0.1956(3) 0.4431(2) 0.0715(12) Uani 1 1 d R . . H7 H -0.1163 -0.1729 0.4388 0.086 Uiso 1 1 calc R . . C8 C -0.0712(2) -0.2309(4) 0.3696(2) 0.0543(10) Uani 1 1 d . . . C9 C -0.1337(2) -0.2367(5) 0.2829(2) 0.0660(11) Uani 1 1 d . . . H9 H -0.1195 -0.2194 0.2402 0.079 Uiso 1 1 calc R . . C10 C -0.1838(2) -0.1130(7) 0.2705(3) 0.1042(17) Uani 1 1 d . . . H10A H -0.1626 -0.0139 0.2807 0.156 Uiso 1 1 calc R . . H10B H -0.2004 -0.1289 0.3097 0.156 Uiso 1 1 calc R . . H10C H -0.2205 -0.1171 0.2131 0.156 Uiso 1 1 calc R . . C11 C -0.1650(3) -0.3960(6) 0.2667(3) 0.1120(19) Uani 1 1 d . . . H11A H -0.1318 -0.4719 0.2747 0.168 Uiso 1 1 calc R . . H11B H -0.2015 -0.4017 0.2093 0.168 Uiso 1 1 calc R . . H11C H -0.1813 -0.4153 0.3059 0.168 Uiso 1 1 calc R . . C12 C 0.1189(2) -0.2872(5) 0.4697(2) 0.0667(11) Uani 1 1 d . . . H12 H 0.1147 -0.2823 0.4128 0.080 Uiso 1 1 calc R . . C13 C 0.1710(2) -0.1686(6) 0.5251(3) 0.0941(15) Uani 1 1 d . . . H13A H 0.2133 -0.1934 0.5288 0.141 Uiso 1 1 calc R . . H13B H 0.1757 -0.1693 0.5812 0.141 Uiso 1 1 calc R . . H13C H 0.1569 -0.0682 0.5003 0.141 Uiso 1 1 calc R . . C14 C 0.14345(15) -0.4491(3) 0.50486(18) 0.117(2) Uani 1 1 d . . . H14A H 0.1870 -0.4658 0.5105 0.176 Uiso 1 1 calc R . . H14B H 0.1126 -0.5241 0.4664 0.176 Uiso 1 1 calc R . . H14C H 0.1462 -0.4591 0.5597 0.176 Uiso 1 1 calc R . . C15 C 0.10510(15) 0.1535(3) 0.31449(18) 0.0690(11) Uani 1 1 d R . . C16 C 0.17238(15) 0.2263(3) 0.36744(18) 0.1111(18) Uani 1 1 d R . . H16A H 0.1938 0.1812 0.4234 0.167 Uiso 1 1 calc R . . H16B H 0.1670 0.3350 0.3719 0.167 Uiso 1 1 calc R . . H16C H 0.1996 0.2093 0.3410 0.167 Uiso 1 1 calc R . . O1 O 0.08768(18) 0.0478(4) 0.34759(16) 0.1012(12) Uani 1 1 d . . . O2 O 0.06748(16) 0.1900(4) 0.2409(2) 0.0945(11) Uani 1 1 d . . . N1 N -0.00284(14) -0.3104(3) 0.30744(14) 0.0423(7) Uani 1 1 d . . . Cu Cu 0.0000 0.00969(7) 0.2500 0.0665(3) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.077(3) 0.0373(19) 0.0417(16) 0.0062(12) 0.0240(17) 0.0004(17) C2 0.044(3) 0.041(2) 0.029(2) 0.000 0.014(2) 0.000 C3 0.059(3) 0.0416(18) 0.0335(16) 0.0020(13) 0.0244(16) -0.0038(17) C4 0.067(3) 0.053(2) 0.0413(18) 0.0016(15) 0.0251(18) -0.0023(19) C5 0.085(3) 0.077(3) 0.0401(19) -0.0030(18) 0.029(2) -0.007(3) C6 0.104(4) 0.080(3) 0.053(2) -0.013(2) 0.050(3) -0.019(3) C7 0.084(3) 0.077(3) 0.075(3) -0.009(2) 0.056(3) -0.007(2) C8 0.060(3) 0.057(2) 0.051(2) -0.0031(16) 0.0308(19) -0.0080(19) C9 0.056(3) 0.085(3) 0.057(2) 0.0026(19) 0.028(2) 0.001(2) C10 0.077(4) 0.123(5) 0.104(3) 0.008(3) 0.037(3) 0.022(3) C11 0.091(4) 0.099(4) 0.101(4) -0.012(3) 0.012(3) -0.028(3) C12 0.064(3) 0.079(3) 0.0429(19) 0.0028(18) 0.0150(18) 0.006(2) C13 0.065(3) 0.105(4) 0.092(3) -0.009(3) 0.022(3) -0.006(3) C14 0.109(5) 0.093(4) 0.126(4) 0.012(3) 0.039(4) 0.023(3) C15 0.086(4) 0.053(2) 0.072(3) -0.004(2) 0.042(3) -0.008(2) C16 0.090(4) 0.099(4) 0.118(4) -0.011(3) 0.031(3) -0.021(3) O1 0.149(3) 0.081(2) 0.0576(16) -0.0070(14) 0.0381(18) -0.044(2) O2 0.089(3) 0.085(2) 0.090(2) 0.0257(17) 0.0279(18) -0.0102(18) N1 0.056(2) 0.0372(14) 0.0337(12) 0.0005(11) 0.0215(12) -0.0011(13) Cu 0.1078(6) 0.0393(4) 0.0438(3) 0.000 0.0303(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C1 1.324(6) 2 ? C1 N1 1.375(4) . ? C2 N1 1.355(3) . ? C2 N1 1.355(3) 2 ? C2 Cu 1.942(4) . ? C3 C8 1.383(5) . ? C3 C4 1.392(5) . ? C3 N1 1.448(4) . ? C4 C5 1.395(5) . ? C4 C12 1.508(6) . ? C5 C6 1.354(5) . ? C6 C7 1.3741 . ? C7 C8 1.400(4) . ? C8 C9 1.515(5) . ? C9 C10 1.506(6) . ? C9 C11 1.518(6) . ? C12 C13 1.519(6) . ? C12 C14 1.531(5) . ? C15 O2 1.215(4) . ? C15 O1 1.259(4) . ? C15 C16 1.4964 . ? C15 Cu 2.440(3) . ? O1 Cu 1.941(3) . ? O2 Cu 2.259(3) . ? Cu O1 1.941(3) 2 ? Cu O2 2.259(3) 2 ? Cu C15 2.440(3) 2 ? 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 C1 N1 107.06(16) 2 . ? N1 C2 N1 103.8(4) . 2 ? N1 C2 Cu 128.11(18) . . ? N1 C2 Cu 128.11(18) 2 . ? C8 C3 C4 124.1(3) . . ? C8 C3 N1 117.9(3) . . ? C4 C3 N1 117.9(3) . . ? C3 C4 C5 116.5(4) . . ? C3 C4 C12 122.9(3) . . ? C5 C4 C12 120.6(3) . . ? C6 C5 C4 121.0(4) . . ? C5 C6 C7 121.4(2) . . ? C6 C7 C8 120.6(2) . . ? C3 C8 C7 116.4(3) . . ? C3 C8 C9 122.5(3) . . ? C7 C8 C9 121.1(4) . . ? C10 C9 C8 113.3(3) . . ? C10 C9 C11 111.6(4) . . ? C8 C9 C11 110.3(3) . . ? C4 C12 C13 113.5(3) . . ? C4 C12 C14 110.8(3) . . ? C13 C12 C14 109.9(3) . . ? O2 C15 O1 119.0(3) . . ? O2 C15 C16 122.9(2) . . ? O1 C15 C16 118.11(19) . . ? O2 C15 Cu 66.91(19) . . ? O1 C15 Cu 52.14(18) . . ? C16 C15 Cu 170.23(7) . . ? C15 O1 Cu 97.0(2) . . ? C15 O2 Cu 83.4(2) . . ? C2 N1 C1 111.0(3) . . ? C2 N1 C3 125.0(3) . . ? C1 N1 C3 124.0(2) . . ? O1 Cu O1 160.36(19) . 2 ? O1 Cu C2 99.82(9) . . ? O1 Cu C2 99.82(9) 2 . ? O1 Cu O2 60.47(12) . . ? O1 Cu O2 104.87(13) 2 . ? C2 Cu O2 133.86(9) . . ? O1 Cu O2 104.87(13) . 2 ? O1 Cu O2 60.47(12) 2 2 ? C2 Cu O2 133.86(9) . 2 ? O2 Cu O2 92.28(18) . 2 ? O1 Cu C15 30.82(10) . . ? O1 Cu C15 133.18(13) 2 . ? C2 Cu C15 120.77(7) . . ? O2 Cu C15 29.66(9) . . ? O2 Cu C15 99.20(11) 2 . ? O1 Cu C15 133.18(13) . 2 ? O1 Cu C15 30.82(10) 2 2 ? C2 Cu C15 120.77(7) . 2 ? O2 Cu C15 99.20(11) . 2 ? O2 Cu C15 29.66(9) 2 2 ? C15 Cu C15 118.45(14) . 2 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.336 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.051