# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Hong Liu' _publ_contact_author_email HLIU@MAIL.SHCNC.AC.CN _publ_section_title ; Gold-catalyzed intramolecular hydroamination of terminal alkynes in aqueous media: efficient and regioselective synthesis of indole-1-carboxamides ; _publ_author_name 'Hong Liu.' # Attachment 'CCDC_721328.cif' data_cd2974 _database_code_depnum_ccdc_archive 'CCDC 721328' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-Benzyl-1H-indole-1-carboxamide ; _chemical_name_common N-Benzyl-1H-indole-1-carboxamide _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N2 O' _chemical_formula_weight 250.29 _exptl_crystal_preparation methanol 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' _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 11.3034(11) _cell_length_b 13.2485(13) _cell_length_c 8.9142(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.277(2) _cell_angle_gamma 90.00 _cell_volume 1324.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 958 _cell_measurement_theta_min 4.759 _cell_measurement_theta_max 39.352 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.185 _exptl_crystal_size_mid 0.167 _exptl_crystal_size_min 0.081 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.79624 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 7163 _diffrn_reflns_av_R_equivalents 0.0989 _diffrn_reflns_av_sigmaI/netI 0.0932 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2601 _reflns_number_gt 1467 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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/[\s^2^(Fo^2^)+(0.0299P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2601 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 0.878 _refine_ls_restrained_S_all 0.878 _refine_ls_shift/su_max 0.003 _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 N1 N 0.71414(16) 0.25439(15) 0.9946(2) 0.0575(5) Uani 1 1 d . . . N3 N 0.90124(14) 0.18593(12) 1.06544(19) 0.0458(5) Uani 1 1 d . . . O1 O 0.74910(12) 0.15871(11) 1.20634(17) 0.0596(5) Uani 1 1 d . . . C2 C 0.78311(19) 0.19760(16) 1.0939(3) 0.0485(6) Uani 1 1 d . . . C4 C 0.95983(19) 0.24309(16) 0.9650(3) 0.0534(6) Uani 1 1 d . . . H4 H 0.9255 0.2953 0.9047 0.064 Uiso 1 1 calc R . . C5 C 1.0719(2) 0.21157(18) 0.9688(3) 0.0612(6) Uani 1 1 d . . . H5 H 1.1285 0.2381 0.9126 0.073 Uiso 1 1 calc R . . C6 C 1.09049(19) 0.12989(17) 1.0742(3) 0.0535(6) Uani 1 1 d . . . C7 C 0.98333(18) 0.11492(15) 1.1342(2) 0.0477(6) Uani 1 1 d . . . C8 C 0.9703(2) 0.03936(17) 1.2386(3) 0.0628(7) Uani 1 1 d . . . H8 H 0.8981 0.0283 1.2757 0.075 Uiso 1 1 calc R . . C9 C 1.0695(3) -0.01835(18) 1.2846(3) 0.0779(8) Uani 1 1 d . . . H9 H 1.0641 -0.0688 1.3560 0.094 Uiso 1 1 calc R . . C10 C 1.1768(3) -0.0041(2) 1.2286(3) 0.0815(8) Uani 1 1 d . . . H10 H 1.2418 -0.0447 1.2627 0.098 Uiso 1 1 calc R . . C11 C 1.1880(2) 0.06914(19) 1.1234(3) 0.0733(7) Uani 1 1 d . . . H11 H 1.2601 0.0783 1.0852 0.088 Uiso 1 1 calc R . . C12 C 0.58742(19) 0.27011(18) 1.0061(3) 0.0635(7) Uani 1 1 d . . . H12A H 0.5675 0.3401 0.9832 0.076 Uiso 1 1 calc R . . H12B H 0.5730 0.2573 1.1094 0.076 Uiso 1 1 calc R . . C13 C 0.50687(18) 0.20343(18) 0.9014(2) 0.0534(6) Uani 1 1 d . . . C14 C 0.5332(2) 0.1041(2) 0.8819(3) 0.0708(7) Uani 1 1 d . . . H14 H 0.6023 0.0770 0.9344 0.085 Uiso 1 1 calc R . . C15 C 0.4595(3) 0.0435(2) 0.7859(4) 0.0859(9) Uani 1 1 d . . . H15 H 0.4791 -0.0240 0.7744 0.103 Uiso 1 1 calc R . . C16 C 0.3571(2) 0.0818(3) 0.7069(3) 0.0841(9) Uani 1 1 d . . . H16 H 0.3077 0.0413 0.6407 0.101 Uiso 1 1 calc R . . C17 C 0.3292(2) 0.1812(3) 0.7277(3) 0.0825(9) Uani 1 1 d . . . H17 H 0.2599 0.2083 0.6760 0.099 Uiso 1 1 calc R . . C18 C 0.4030(2) 0.2407(2) 0.8242(3) 0.0689(7) Uani 1 1 d . . . H18 H 0.3824 0.3077 0.8379 0.083 Uiso 1 1 calc R . . H1 H 0.7372(18) 0.2749(16) 0.908(3) 0.071(8) Uiso 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 N1 0.0481(12) 0.0769(14) 0.0484(13) 0.0046(11) 0.0091(10) 0.0078(10) N3 0.0444(10) 0.0467(10) 0.0463(11) -0.0015(9) 0.0052(9) -0.0024(8) O1 0.0600(10) 0.0697(11) 0.0504(10) 0.0035(8) 0.0121(8) -0.0068(8) C2 0.0500(14) 0.0515(14) 0.0440(14) -0.0073(11) 0.0062(12) -0.0046(11) C4 0.0534(14) 0.0572(14) 0.0498(14) 0.0034(11) 0.0071(11) -0.0082(11) C5 0.0489(14) 0.0716(17) 0.0648(16) 0.0033(13) 0.0138(12) -0.0052(12) C6 0.0468(14) 0.0534(14) 0.0592(16) -0.0118(12) 0.0028(12) 0.0019(11) C7 0.0504(14) 0.0399(12) 0.0510(14) -0.0079(11) -0.0011(11) -0.0008(10) C8 0.0701(17) 0.0482(14) 0.0692(18) 0.0012(13) 0.0051(14) 0.0014(12) C9 0.099(2) 0.0539(16) 0.080(2) 0.0093(14) 0.0064(18) 0.0078(15) C10 0.081(2) 0.0672(18) 0.092(2) -0.0016(17) -0.0050(17) 0.0229(15) C11 0.0619(17) 0.0703(18) 0.087(2) -0.0096(16) 0.0049(15) 0.0083(14) C12 0.0529(15) 0.0787(17) 0.0600(16) -0.0027(13) 0.0109(12) 0.0147(13) C13 0.0416(13) 0.0690(16) 0.0514(14) 0.0080(13) 0.0129(11) 0.0089(12) C14 0.0595(16) 0.0702(18) 0.081(2) 0.0105(15) 0.0006(15) 0.0068(14) C15 0.083(2) 0.0692(19) 0.105(2) 0.0004(17) 0.010(2) -0.0029(17) C16 0.0640(19) 0.102(2) 0.086(2) 0.0004(19) 0.0086(17) -0.0223(17) C17 0.0477(16) 0.118(3) 0.081(2) 0.0103(19) 0.0018(15) 0.0088(17) C18 0.0523(15) 0.0828(19) 0.0721(19) 0.0080(15) 0.0099(14) 0.0131(14) _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 N1 C2 1.335(3) . ? N1 C12 1.464(3) . ? N1 H1 0.89(2) . ? N3 C2 1.399(2) . ? N3 C4 1.401(2) . ? N3 C7 1.406(2) . ? O1 C2 1.231(2) . ? C4 C5 1.330(3) . ? C4 H4 0.9300 . ? C5 C6 1.431(3) . ? C5 H5 0.9300 . ? C6 C11 1.390(3) . ? C6 C7 1.399(3) . ? C7 C8 1.387(3) . ? C8 C9 1.376(3) . ? C8 H8 0.9300 . ? C9 C10 1.382(4) . ? C9 H9 0.9300 . ? C10 C11 1.367(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.505(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.365(3) . ? C13 C18 1.375(3) . ? C14 C15 1.375(3) . ? C14 H14 0.9300 . ? C15 C16 1.374(4) . ? C15 H15 0.9300 . ? C16 C17 1.371(4) . ? C16 H16 0.9300 . ? C17 C18 1.369(3) . ? C17 H17 0.9300 . ? C18 H18 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 C2 N1 C12 121.9(2) . . ? C2 N1 H1 122.5(14) . . ? C12 N1 H1 114.5(14) . . ? C2 N3 C4 126.53(18) . . ? C2 N3 C7 125.96(18) . . ? C4 N3 C7 107.50(16) . . ? O1 C2 N1 124.0(2) . . ? O1 C2 N3 120.3(2) . . ? N1 C2 N3 115.7(2) . . ? C5 C4 N3 109.9(2) . . ? C5 C4 H4 125.1 . . ? N3 C4 H4 125.1 . . ? C4 C5 C6 108.3(2) . . ? C4 C5 H5 125.8 . . ? C6 C5 H5 125.8 . . ? C11 C6 C7 119.2(2) . . ? C11 C6 C5 133.6(2) . . ? C7 C6 C5 107.23(19) . . ? C8 C7 C6 122.0(2) . . ? C8 C7 N3 130.9(2) . . ? C6 C7 N3 107.10(19) . . ? C9 C8 C7 116.7(2) . . ? C9 C8 H8 121.6 . . ? C7 C8 H8 121.6 . . ? C8 C9 C10 122.4(2) . . ? C8 C9 H9 118.8 . . ? C10 C9 H9 118.8 . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C6 119.3(2) . . ? C10 C11 H11 120.4 . . ? C6 C11 H11 120.4 . . ? N1 C12 C13 113.18(18) . . ? N1 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? N1 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C18 117.9(2) . . ? C14 C13 C12 121.3(2) . . ? C18 C13 C12 120.7(2) . . ? C13 C14 C15 121.1(2) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 120.5(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 118.6(3) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? C18 C17 C16 120.4(3) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C13 121.4(3) . . ? C17 C18 H18 119.3 . . ? C13 C18 H18 119.3 . . ? 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 C12 N1 C2 O1 -4.1(3) . . . . ? C12 N1 C2 N3 177.50(18) . . . . ? C4 N3 C2 O1 -164.19(19) . . . . ? C7 N3 C2 O1 15.1(3) . . . . ? C4 N3 C2 N1 14.2(3) . . . . ? C7 N3 C2 N1 -166.48(19) . . . . ? C2 N3 C4 C5 179.2(2) . . . . ? C7 N3 C4 C5 -0.2(2) . . . . ? N3 C4 C5 C6 0.4(3) . . . . ? C4 C5 C6 C11 -179.9(2) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? C11 C6 C7 C8 -1.8(3) . . . . ? C5 C6 C7 C8 178.7(2) . . . . ? C11 C6 C7 N3 179.89(19) . . . . ? C5 C6 C7 N3 0.4(2) . . . . ? C2 N3 C7 C8 2.3(3) . . . . ? C4 N3 C7 C8 -178.3(2) . . . . ? C2 N3 C7 C6 -179.53(18) . . . . ? C4 N3 C7 C6 -0.1(2) . . . . ? C6 C7 C8 C9 2.1(3) . . . . ? N3 C7 C8 C9 -179.9(2) . . . . ? C7 C8 C9 C10 -1.2(4) . . . . ? C8 C9 C10 C11 -0.1(4) . . . . ? C9 C10 C11 C6 0.5(4) . . . . ? C7 C6 C11 C10 0.4(4) . . . . ? C5 C6 C11 C10 179.7(2) . . . . ? C2 N1 C12 C13 -99.5(3) . . . . ? N1 C12 C13 C14 42.1(3) . . . . ? N1 C12 C13 C18 -139.0(2) . . . . ? C18 C13 C14 C15 1.2(4) . . . . ? C12 C13 C14 C15 -179.9(2) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C14 C15 C16 C17 -1.0(4) . . . . ? C15 C16 C17 C18 0.7(4) . . . . ? C16 C17 C18 C13 0.7(4) . . . . ? C14 C13 C18 C17 -1.6(3) . . . . ? C12 C13 C18 C17 179.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.89(2) 2.02(2) 2.889(3) 165.1(19) 4_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.167 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.040