# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Jonathan Ellman' 'Robert Bergman' 'Hitoshi Harada' 'Andy S. Tsai' 'Rebecca M. Wilson' _publ_contact_author_name ' Jonathan Ellman' _publ_contact_author_email JELLMAN@BERKELEY.EDU _publ_section_title ; Rhodium Catalyzed Enantioselective Cylization of Substituted Imidazoles via C-H Bond Activation ; # Attachment 'B902878A.cif' data_ellman03 _database_code_depnum_ccdc_archive 'CCDC 727522' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ellman03 ; _chemical_name_common HHII-149a _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 Cl N2' _chemical_formula_weight 208.68 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 14.8792(16) _cell_length_b 7.4397(8) _cell_length_c 10.0119(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1108.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8650 _cell_measurement_theta_min 4.42 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 2.737 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8530 _exptl_absorpt_correction_T_max 0.9473 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 0.5 _diffrn_refln_scan_rate 5 _space_group.centring_type primitive _space_group.IT_number 18 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.648 34 17 HCl 2 0.500 0.500 0.352 34 17 HCl _platon_squeeze_details ; ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'microfocus rotating anode' _diffrn_radiation_monochromator 'HELIOS multilayer mirrors' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 9520 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.42 _diffrn_reflns_theta_max 68.24 _reflns_number_total 1990 _reflns_number_gt 1956 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-2004 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _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^)+(0.0521P)^2^+0.6507P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 1990 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 0.07776(15) 0.8203(3) 0.0904(2) 0.0218(5) Uani 1 1 d . . . C2 C 0.00362(18) 0.7627(3) 0.0169(2) 0.0266(5) Uani 1 1 d . . . H2 H 0.0032 0.7657 -0.0780 0.032 Uiso 1 1 calc R . . C3 C -0.06932(16) 0.7010(3) 0.0892(3) 0.0287(6) Uani 1 1 d . . . H3 H -0.1208 0.6592 0.0424 0.034 Uiso 1 1 calc R . . C4 C -0.07000(15) 0.6980(3) 0.2288(3) 0.0264(5) Uani 1 1 d . . . H4 H -0.1218 0.6546 0.2740 0.032 Uiso 1 1 calc R . . C5 C 0.00254(16) 0.7563(3) 0.3027(2) 0.0223(4) Uani 1 1 d . . . H5 H 0.0020 0.7556 0.3976 0.027 Uiso 1 1 calc R . . C6 C 0.07661(14) 0.8162(3) 0.2307(2) 0.0202(4) Uani 1 1 d . . . C7 C 0.20773(15) 0.9181(3) 0.3946(2) 0.0226(5) Uani 1 1 d . . . H7A H 0.2305 0.8037 0.4322 0.027 Uiso 1 1 calc R . . H7B H 0.1697 0.9790 0.4618 0.027 Uiso 1 1 calc R . . C8 C 0.28528(14) 1.0402(3) 0.3474(2) 0.0234(5) Uani 1 1 d . . . H8 H 0.2659 1.1679 0.3588 0.028 Uiso 1 1 calc R . . C9 C 0.29575(14) 1.0033(3) 0.19581(19) 0.0226(4) Uani 1 1 d . . . H9A H 0.3088 1.1152 0.1459 0.027 Uiso 1 1 calc R . . H9B H 0.3438 0.9144 0.1782 0.027 Uiso 1 1 calc R . . C10 C 0.20581(15) 0.9305(3) 0.1611(2) 0.0197(4) Uani 1 1 d . . . C11 C 0.37108(15) 1.0135(4) 0.4260(2) 0.0326(5) Uani 1 1 d . . . H11A H 0.3594 1.0350 0.5210 0.049 Uiso 1 1 calc R . . H11B H 0.4168 1.0981 0.3943 0.049 Uiso 1 1 calc R . . H11C H 0.3926 0.8901 0.4137 0.049 Uiso 1 1 calc R . . N1 N 0.15987(13) 0.8918(2) 0.05172(18) 0.0217(4) Uani 1 1 d . . . H1 H 0.1781 0.9085 -0.0310 0.026 Uiso 1 1 calc R . . N2 N 0.15862(12) 0.8885(2) 0.26887(18) 0.0188(4) Uani 1 1 d . . . Cl1 Cl 0.29405(3) 0.51712(7) 0.23002(5) 0.02589(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0251(11) 0.0176(11) 0.0228(11) -0.0008(9) -0.0008(9) 0.0039(9) C2 0.0314(12) 0.0232(11) 0.0254(10) -0.0034(9) -0.0077(12) 0.0062(10) C3 0.0248(12) 0.0232(13) 0.0380(14) -0.0029(10) -0.0117(10) -0.0002(10) C4 0.0194(10) 0.0210(11) 0.0387(13) 0.0025(11) 0.0018(10) 0.0001(8) C5 0.0220(10) 0.0210(10) 0.0241(10) 0.0024(8) 0.0010(10) 0.0031(9) C6 0.0202(10) 0.0168(9) 0.0236(11) -0.0018(9) -0.0023(8) 0.0028(8) C7 0.0239(11) 0.0277(11) 0.0163(10) -0.0008(8) -0.0034(9) 0.0013(11) C8 0.0219(10) 0.0255(11) 0.0228(11) -0.0007(9) -0.0009(9) -0.0012(9) C9 0.0227(10) 0.0230(10) 0.0221(10) 0.0000(9) 0.0023(8) -0.0021(10) C10 0.0227(10) 0.0167(9) 0.0199(10) -0.0006(8) 0.0020(9) 0.0037(9) C11 0.0248(11) 0.0405(14) 0.0326(12) -0.0002(13) -0.0060(9) -0.0013(12) N1 0.0264(10) 0.0222(10) 0.0165(9) -0.0002(7) 0.0007(8) 0.0030(8) N2 0.0193(8) 0.0208(8) 0.0163(8) 0.0010(7) -0.0001(7) 0.0008(7) Cl1 0.0307(3) 0.0251(3) 0.0218(3) -0.0021(2) 0.00326(19) -0.0001(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 C1 N1 1.388(3) . ? C1 C2 1.394(3) . ? C1 C6 1.405(3) . ? C2 C3 1.383(4) . ? C2 H2 0.9500 . ? C3 C4 1.398(4) . ? C3 H3 0.9500 . ? C4 C5 1.378(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(3) . ? C5 H5 0.9500 . ? C6 N2 1.387(3) . ? C7 N2 1.472(3) . ? C7 C8 1.542(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C11 1.513(3) . ? C8 C9 1.551(3) . ? C8 H8 1.0000 . ? C9 C10 1.485(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N1 1.322(3) . ? C10 N2 1.325(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? N1 H1 0.8800 . ? 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 N1 C1 C2 131.8(2) . . ? N1 C1 C6 107.3(2) . . ? C2 C1 C6 120.8(2) . . ? C3 C2 C1 116.5(2) . . ? C3 C2 H2 121.7 . . ? C1 C2 H2 121.7 . . ? C2 C3 C4 122.3(2) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C5 C4 C3 121.7(2) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 116.3(2) . . ? C4 C5 H5 121.8 . . ? C6 C5 H5 121.8 . . ? N2 C6 C5 132.7(2) . . ? N2 C6 C1 104.9(2) . . ? C5 C6 C1 122.3(2) . . ? N2 C7 C8 101.41(16) . . ? N2 C7 H7A 111.5 . . ? C8 C7 H7A 111.5 . . ? N2 C7 H7B 111.5 . . ? C8 C7 H7B 111.5 . . ? H7A C7 H7B 109.3 . . ? C11 C8 C7 113.26(18) . . ? C11 C8 C9 113.66(18) . . ? C7 C8 C9 105.70(17) . . ? C11 C8 H8 108.0 . . ? C7 C8 H8 108.0 . . ? C9 C8 H8 108.0 . . ? C10 C9 C8 101.73(17) . . ? C10 C9 H9A 111.4 . . ? C8 C9 H9A 111.4 . . ? C10 C9 H9B 111.4 . . ? C8 C9 H9B 111.4 . . ? H9A C9 H9B 109.3 . . ? N1 C10 N2 110.43(19) . . ? N1 C10 C9 137.7(2) . . ? N2 C10 C9 111.88(18) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 N1 C1 107.90(18) . . ? C10 N1 H1 126.0 . . ? C1 N1 H1 126.0 . . ? C10 N2 C6 109.45(19) . . ? C10 N2 C7 113.46(16) . . ? C6 N2 C7 136.92(19) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.452 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.053