# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Steven Nolan' _publ_contact_author_email SNOLAN@ICIQ.ES _publ_section_title ; A [(NHC)CuCl] (NHC= N-Heterocyclic Carbene) Complex as Latent Click Catalyst ; loop_ _publ_author_name 'Steven Nolan' 'Silvia Diez-Gonzalez' 'Edwin D Stevens' # Attachment 'Nol164b.cif' data_nol164 _database_code_depnum_ccdc_archive 'CCDC 649761' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H42 Cl5 Cu N2' _chemical_formula_weight 659.44 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' Cl Cl 0.1484 0.1585 '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 P2(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 9.5227(11) _cell_length_b 16.4203(19) _cell_length_c 11.0548(13) _cell_angle_alpha 90.00 _cell_angle_beta 103.810(2) _cell_angle_gamma 90.00 _cell_volume 1678.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11340 _cell_measurement_theta_min 2.313 _cell_measurement_theta_max 28.823 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 1.069 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.895335 _exptl_absorpt_correction_T_max 0.965212 _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 '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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13663 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2289 _reflns_number_gt 1973 _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. Both of the dichloromethane solvent molecules in the structure are disordered about the crystallographic mirror plane. ; _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^)+(0.0724P)^2^+7.1407P] 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 2289 _refine_ls_number_parameters 247 _refine_ls_number_restraints 143 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0801 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.02045(9) 0.2500 0.92722(8) 0.0194(3) Uani 1 2 d SU . . Cl1 Cl -0.2039(2) 0.2500 0.91763(19) 0.0300(5) Uani 1 2 d SU . . N1 N 0.2972(4) 0.1841(3) 0.9116(4) 0.0166(9) Uani 1 1 d U . . C1 C 0.2438(5) 0.1021(3) 0.9121(5) 0.0190(11) Uani 1 1 d U . . C2 C 0.1628(6) 0.0697(3) 0.7994(5) 0.0278(13) Uani 1 1 d U . . Cl2 Cl 0.6630(4) 0.2223(2) 1.2884(4) 0.0584(12) Uani 0.50 1 d PDU . 1 C3 C 0.1112(8) -0.0099(4) 0.8044(7) 0.0443(17) Uani 1 1 d U . . H3 H 0.063(6) -0.026(3) 0.739(5) 0.019(15) Uiso 1 1 d . . . Cl3 Cl 0.9679(3) 0.2608(14) 1.3036(3) 0.037(3) Uani 0.50 1 d PDU . 1 C4 C 0.1380(9) -0.0531(4) 0.9126(7) 0.0483(18) Uani 1 1 d U . . H4 H 0.113(6) -0.100(4) 0.914(5) 0.031(17) Uiso 1 1 d . . . C5 C 0.2199(7) -0.0210(4) 1.0197(6) 0.0360(15) Uani 1 1 d U . . H5 H 0.238(6) -0.048(4) 1.090(6) 0.035(17) Uiso 1 1 d . . . Cl4 Cl 0.4598(5) 0.2658(6) 0.5564(3) 0.107(4) Uani 0.50 1 d PDU . 1 C6 C 0.2743(6) 0.0578(3) 1.0226(5) 0.0230(12) Uani 1 1 d U . . C7 C 0.1287(7) 0.1159(4) 0.6776(6) 0.0370(15) Uani 1 1 d U . . H7 H 0.169(6) 0.160(4) 0.691(5) 0.021(16) Uiso 1 1 d . . . Cl5 Cl 0.5850(5) 0.1078(3) 0.5686(4) 0.0791(13) Uani 0.50 1 d PDU . 1 C8 C -0.0327(9) 0.1335(5) 0.6358(7) 0.0505(19) Uani 1 1 d U . . H8A H -0.091(9) 0.086(5) 0.628(7) 0.076 Uiso 1 1 d . . . H8B H -0.057(9) 0.161(5) 0.566(7) 0.076 Uiso 1 1 d . . . H8C H -0.073(8) 0.167(5) 0.700(7) 0.076 Uiso 1 1 d . . . C9 C 0.1850(7) 0.0733(4) 0.5769(6) 0.0452(17) Uani 1 1 d U . . H9A H 0.2897 0.0655 0.6056 0.068 Uiso 1 1 calc R . . H9B H 0.1640 0.1067 0.5013 0.068 Uiso 1 1 calc R . . H9C H 0.1376 0.0202 0.5589 0.068 Uiso 1 1 calc R . . C10 C 0.3613(7) 0.0938(4) 1.1430(5) 0.0299(14) Uani 1 1 d U . . H10 H 0.409(6) 0.136(3) 1.126(5) 0.018(15) Uiso 1 1 d . . . C11 C 0.2668(8) 0.1162(5) 1.2285(6) 0.059(2) Uani 1 1 d U . . H11A H 0.1966 0.1575 1.1885 0.088 Uiso 1 1 calc R . . H11B H 0.3265 0.1381 1.3064 0.088 Uiso 1 1 calc R . . H11C H 0.2153 0.0677 1.2464 0.088 Uiso 1 1 calc R . . C12 C 0.4856(11) 0.0400(7) 1.2080(9) 0.091(4) Uani 1 1 d U . . H12A H 0.551(12) 0.063(7) 1.278(11) 0.136 Uiso 1 1 d . . . H12B H 0.548(13) 0.027(7) 1.165(11) 0.136 Uiso 1 1 d . . . H12C H 0.451(14) 0.004(8) 1.240(12) 0.136 Uiso 1 1 d . . . C13 C 0.2169(7) 0.2500 0.9184(6) 0.0143(15) Uani 1 2 d SU . . C14 C 0.4420(6) 0.2040(4) 0.8952(6) 0.0241(13) Uani 1 1 d U . . H14A H 0.451(5) 0.183(3) 0.829(5) 0.008(13) Uiso 1 1 d . . . H14B H 0.508(7) 0.187(4) 0.965(6) 0.037(18) Uiso 1 1 d . . . C15 C 0.7904(11) 0.2825(8) 1.2433(13) 0.048(4) Uani 0.50 1 d PDU . 1 H15A H 0.7722 0.2796 1.1514 0.057 Uiso 0.50 1 calc PR . 1 H15B H 0.7736 0.3396 1.2650 0.057 Uiso 0.50 1 calc PR . 1 C16 C 0.6172(14) 0.2106(8) 0.5913(13) 0.061(3) Uani 0.50 1 d PDU . 1 H16A H 0.6679 0.2203 0.6793 0.073 Uiso 0.50 1 calc PR . 1 H16B H 0.6810 0.2293 0.5381 0.073 Uiso 0.50 1 calc PR . 1 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 Cu1 0.0146(5) 0.0189(6) 0.0252(6) 0.000 0.0055(4) 0.000 Cl1 0.0158(10) 0.0387(13) 0.0364(12) 0.000 0.0079(9) 0.000 N1 0.010(2) 0.018(2) 0.020(2) -0.0037(18) -0.0002(17) -0.0005(17) C1 0.013(2) 0.015(2) 0.027(3) -0.003(2) 0.002(2) 0.009(2) C2 0.035(3) 0.016(3) 0.029(3) -0.006(2) 0.001(2) 0.004(2) Cl2 0.053(2) 0.058(3) 0.067(2) -0.0008(16) 0.0201(18) -0.0259(16) C3 0.070(5) 0.019(3) 0.033(3) -0.008(3) -0.010(3) 0.000(3) Cl3 0.0429(14) 0.023(11) 0.0464(15) 0.0006(19) 0.0111(12) -0.005(2) C4 0.078(5) 0.012(3) 0.049(4) 0.000(3) 0.004(3) -0.008(3) C5 0.059(4) 0.017(3) 0.030(3) 0.006(3) 0.007(3) 0.010(3) Cl4 0.092(3) 0.183(9) 0.047(2) 0.023(4) 0.020(2) 0.099(6) C6 0.023(3) 0.020(3) 0.027(3) -0.003(2) 0.006(2) 0.010(2) C7 0.052(4) 0.020(3) 0.028(3) -0.007(2) -0.013(3) -0.004(3) Cl5 0.053(2) 0.101(3) 0.078(3) 0.005(3) 0.007(2) -0.013(2) C8 0.062(4) 0.047(5) 0.032(4) -0.004(3) -0.009(3) 0.018(4) C9 0.045(4) 0.051(4) 0.033(3) -0.005(3) -0.004(3) -0.001(3) C10 0.031(3) 0.032(4) 0.025(3) -0.002(3) 0.004(2) 0.003(3) C11 0.046(4) 0.088(6) 0.042(4) -0.033(4) 0.009(3) 0.009(4) C12 0.068(6) 0.121(9) 0.061(6) -0.033(6) -0.029(5) 0.061(6) C13 0.015(3) 0.017(3) 0.007(3) 0.000 -0.005(3) 0.000 C14 0.016(3) 0.038(3) 0.019(3) 0.000(3) 0.007(3) 0.005(2) C15 0.036(5) 0.054(9) 0.062(9) 0.024(6) 0.030(6) 0.009(5) C16 0.053(9) 0.097(7) 0.037(8) 0.017(7) 0.016(7) 0.035(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 Cu1 C13 1.896(7) . ? Cu1 Cl1 2.114(2) . ? N1 C13 1.337(6) . ? N1 C1 1.440(7) . ? N1 C14 1.469(7) . ? C1 C6 1.392(7) . ? C1 C2 1.404(7) . ? C2 C3 1.402(9) . ? C2 C7 1.511(8) . ? Cl2 Cl2 0.911(7) 4_565 ? Cl2 C15 1.420(11) 4_565 ? Cl2 C15 1.729(11) . ? C3 C4 1.361(10) . ? Cl3 Cl3 0.36(5) 4_565 ? Cl3 C15 1.700(12) . ? Cl3 C15 1.808(15) 4_565 ? C4 C5 1.359(9) . ? C5 C6 1.391(8) . ? Cl4 Cl4 0.52(2) 4_565 ? Cl4 C16 1.506(13) 4_565 ? Cl4 C16 1.715(12) . ? Cl4 Cl5 2.380(12) 4_565 ? C6 C10 1.511(8) . ? C7 C9 1.516(9) . ? C7 C8 1.523(10) . ? Cl5 C16 1.722(14) . ? Cl5 Cl4 2.380(12) 4_565 ? C10 C11 1.498(9) . ? C10 C12 1.513(11) . ? C13 N1 1.337(6) 4_565 ? C14 C14 1.511(12) 4_565 ? 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 C13 Cu1 Cl1 174.4(2) . . ? C13 N1 C1 123.3(4) . . ? C13 N1 C14 113.2(4) . . ? C1 N1 C14 123.4(4) . . ? C6 C1 C2 122.4(5) . . ? C6 C1 N1 119.5(5) . . ? C2 C1 N1 118.1(5) . . ? C3 C2 C1 116.2(5) . . ? C3 C2 C7 120.0(5) . . ? C1 C2 C7 123.8(5) . . ? Cl2 Cl2 C15 93.2(6) 4_565 4_565 ? Cl2 Cl2 C15 55.1(5) 4_565 . ? C15 Cl2 C15 38.1(9) 4_565 . ? C4 C3 C2 121.8(6) . . ? Cl3 Cl3 C15 102.1(9) 4_565 . ? Cl3 Cl3 C15 66.8(8) 4_565 4_565 ? C15 Cl3 C15 35.2(9) . 4_565 ? C5 C4 C3 120.8(7) . . ? C4 C5 C6 120.9(6) . . ? Cl4 Cl4 C16 104.9(7) 4_565 4_565 ? Cl4 Cl4 C16 58.1(6) 4_565 . ? C16 Cl4 C16 46.8(10) 4_565 . ? Cl4 Cl4 Cl5 150.63(16) 4_565 4_565 ? C16 Cl4 Cl5 46.1(6) 4_565 4_565 ? C16 Cl4 Cl5 92.8(6) . 4_565 ? C5 C6 C1 117.8(5) . . ? C5 C6 C10 120.5(5) . . ? C1 C6 C10 121.6(5) . . ? C2 C7 C9 112.6(5) . . ? C2 C7 C8 110.6(6) . . ? C9 C7 C8 111.9(5) . . ? C16 Cl5 Cl4 39.1(4) . 4_565 ? C11 C10 C6 111.4(5) . . ? C11 C10 C12 111.3(7) . . ? C6 C10 C12 113.1(6) . . ? N1 C13 N1 108.0(6) 4_565 . ? N1 C13 Cu1 126.0(3) 4_565 . ? N1 C13 Cu1 126.0(3) . . ? N1 C14 C14 102.8(3) . 4_565 ? Cl3 C15 Cl2 117.9(9) . . ? Cl4 C16 Cl5 111.7(9) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.705 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.096