# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_general _database_code_CSD 177615 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Muthusamy, Sengodagounder' 'Babu, Srinivasarao A.' 'Dastidar, Parthasarathy' 'Gunanathan, Chidambaram' 'Suresh, Eringathodi' _journal_name_full 'Chemical Communications' _publ_contact_author_name 'Dr. Sengodagounder Muthusamy' _publ_contact_author_address ; Catalysis discipline CSMCRI G. B. Marg Bhavnagar Gujarat 364 002 INDIA ; _publ_contact_author_email smuthus@yahoo.com _publ_section_title ; First example of regiospecific intermolecular C-H insertion reactions of cyclic rhodium carbenoids: Novel synthesis of 3,3'-indolyloxindoles ; _audit_creation_method SHELXL-97 _chemical_name_systematic '1,3-Dihydro-1'H-[3,3']biindolyl-2-one' _chemical_name_common Biindole _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 N2 O' _chemical_formula_weight 248.28 _chemical_melting_point 449-451 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' '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.137(4) _cell_length_b 4.6810(10) _cell_length_c 23.871(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.85(2) _cell_angle_gamma 90.00 _cell_volume 1238.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description Plates _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type Mo K\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method 'omega-two theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1hr _diffrn_standards_decay_% nil _diffrn_reflns_number 2178 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 24.91 _reflns_number_total 2178 _reflns_number_gt 1507 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4-PC _computing_cell_refinement CAD4-PC _computing_data_reduction NRCVAX _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP, PLATON' _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0967P)^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 2178 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1315 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.89260(14) 0.5853(4) 0.23844(6) 0.0555(5) Uani 1 d . . . N1 N 0.77447(16) 0.2603(4) 0.18618(7) 0.0436(5) Uani 1 d . . . C2' C 1.1042(2) 0.1066(5) 0.20295(9) 0.0417(5) Uani 1 d . . . C7 C 0.6925(2) -0.0704(5) 0.10897(10) 0.0505(6) Uani 1 d . . . C4 C 0.8912(2) 0.1139(5) 0.05484(9) 0.0437(6) Uani 1 d . . . C3' C 1.07244(18) 0.3120(4) 0.16412(8) 0.0336(5) Uani 1 d . . . C7A C 0.77382(18) 0.1236(4) 0.13345(8) 0.0372(5) Uani 1 d . . . C2 C 0.86998(18) 0.4361(5) 0.19627(8) 0.0394(5) Uani 1 d . . . C3 C 0.94650(17) 0.4180(5) 0.14652(8) 0.0352(5) Uani 1 d . . . C5 C 0.8088(2) -0.0831(6) 0.02907(10) 0.0529(6) Uani 1 d . . . C3A C 0.87307(18) 0.2179(5) 0.10729(8) 0.0352(5) Uani 1 d . . . C6 C 0.7113(2) -0.1718(6) 0.05600(11) 0.0559(7) Uani 1 d . . . N1' N 1.22669(17) 0.0569(4) 0.20538(8) 0.0457(5) Uani 1 d . . . C3A' C 1.17996(18) 0.3898(4) 0.13900(8) 0.0342(5) Uani 1 d . . . C7A' C 1.27473(19) 0.2245(5) 0.16613(8) 0.0385(5) Uani 1 d . . . C6' C 1.4144(2) 0.4305(7) 0.11011(12) 0.0616(8) Uani 1 d . . . C7' C 1.3927(2) 0.2447(6) 0.15229(11) 0.0515(6) Uani 1 d . . . C4' C 1.2055(2) 0.5818(5) 0.09709(9) 0.0420(6) Uani 1 d . . . C5' C 1.3222(2) 0.5979(6) 0.08260(11) 0.0554(7) Uani 1 d . . . H7' H 1.452(2) 0.112(5) 0.1745(10) 0.058(7) Uiso 1 d . . . H5' H 1.343(2) 0.728(6) 0.0517(11) 0.072(8) Uiso 1 d . . . H2' H 1.0533(19) -0.001(5) 0.2280(9) 0.045(6) Uiso 1 d . . . H5 H 0.824(2) -0.148(5) -0.0069(11) 0.071(8) Uiso 1 d . . . H1N H 0.714(2) 0.221(5) 0.2133(10) 0.059(7) Uiso 1 d . . . H4 H 0.963(2) 0.187(5) 0.0357(9) 0.053(7) Uiso 1 d . . . H7 H 0.624(2) -0.137(5) 0.1269(10) 0.061(7) Uiso 1 d . . . H3 H 0.9462(19) 0.613(5) 0.1296(8) 0.039(6) Uiso 1 d . . . H4' H 1.142(2) 0.700(5) 0.0782(9) 0.046(6) Uiso 1 d . . . H6' H 1.498(3) 0.457(6) 0.0953(11) 0.074(8) Uiso 1 d . . . H6 H 0.653(2) -0.312(6) 0.0366(11) 0.070(8) Uiso 1 d . . . H2N H 1.270(3) -0.090(6) 0.2237(12) 0.086(10) Uiso 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 O1 0.0485(9) 0.0717(12) 0.0485(9) -0.0215(9) 0.0156(7) -0.0048(9) N1 0.0385(10) 0.0516(12) 0.0434(10) -0.0028(9) 0.0177(8) -0.0058(9) C2' 0.0469(13) 0.0402(12) 0.0387(11) 0.0002(10) 0.0081(9) -0.0006(11) C7 0.0397(13) 0.0507(15) 0.0620(15) -0.0039(12) 0.0089(11) -0.0097(12) C4 0.0440(12) 0.0520(14) 0.0361(11) -0.0020(10) 0.0091(9) 0.0034(11) C3' 0.0358(11) 0.0330(11) 0.0325(10) -0.0052(9) 0.0067(8) -0.0026(9) C7A 0.0353(11) 0.0384(12) 0.0389(11) 0.0001(9) 0.0080(8) 0.0016(9) C2 0.0353(11) 0.0452(13) 0.0392(11) -0.0017(10) 0.0104(8) 0.0027(10) C3 0.0338(10) 0.0359(12) 0.0373(11) -0.0001(10) 0.0107(8) 0.0012(9) C5 0.0569(15) 0.0603(16) 0.0409(13) -0.0112(12) 0.0020(11) -0.0009(13) C3A 0.0338(10) 0.0359(11) 0.0363(10) 0.0042(9) 0.0054(8) 0.0015(9) C6 0.0487(14) 0.0570(16) 0.0603(15) -0.0107(13) -0.0018(11) -0.0079(13) N1' 0.0496(11) 0.0421(11) 0.0441(10) 0.0026(9) -0.0018(8) 0.0091(10) C3A' 0.0347(10) 0.0359(11) 0.0322(10) -0.0080(9) 0.0041(8) -0.0004(9) C7A' 0.0397(11) 0.0388(12) 0.0366(11) -0.0089(10) 0.0021(9) 0.0014(10) C6' 0.0353(13) 0.0773(19) 0.0743(17) -0.0201(16) 0.0155(12) -0.0135(14) C7' 0.0364(12) 0.0579(16) 0.0590(14) -0.0129(14) -0.0009(10) 0.0036(12) C4' 0.0435(12) 0.0435(13) 0.0398(11) 0.0006(10) 0.0083(9) -0.0059(11) C5' 0.0533(15) 0.0612(16) 0.0549(14) -0.0036(13) 0.0218(12) -0.0151(13) _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 O1 C2 1.230(2) . ? N1 C2 1.347(3) . ? N1 C7A 1.411(3) . ? C2' C3' 1.357(3) . ? C2' N1' 1.379(3) . ? C7 C7A 1.370(3) . ? C7 C6 1.386(4) . ? C4 C3A 1.377(3) . ? C4 C5 1.398(3) . ? C3' C3A' 1.440(3) . ? C3' C3 1.507(3) . ? C7A C3A 1.395(3) . ? C2 C3 1.533(3) . ? C3 C3A 1.505(3) . ? C5 C6 1.381(4) . ? N1' C7A' 1.372(3) . ? C3A' C4' 1.395(3) . ? C3A' C7A' 1.412(3) . ? C7A' C7' 1.390(3) . ? C6' C7' 1.371(4) . ? C6' C5' 1.401(4) . ? C4' C5' 1.381(3) . ? 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 C7A 111.63(17) . . ? C3' C2' N1' 109.6(2) . . ? C7A C7 C6 117.5(2) . . ? C3A C4 C5 118.9(2) . . ? C2' C3' C3A' 107.09(19) . . ? C2' C3' C3 126.46(19) . . ? C3A' C3' C3 126.21(18) . . ? C7 C7A C3A 122.5(2) . . ? C7 C7A N1 128.60(19) . . ? C3A C7A N1 108.87(18) . . ? O1 C2 N1 125.82(19) . . ? O1 C2 C3 125.58(19) . . ? N1 C2 C3 108.59(18) . . ? C3A C3 C3' 113.57(17) . . ? C3A C3 C2 101.93(17) . . ? C3' C3 C2 112.18(17) . . ? C6 C5 C4 120.4(2) . . ? C4 C3A C7A 119.4(2) . . ? C4 C3A C3 131.68(19) . . ? C7A C3A C3 108.86(17) . . ? C5 C6 C7 121.3(2) . . ? C7A' N1' C2' 109.12(19) . . ? C4' C3A' C7A' 118.99(19) . . ? C4' C3A' C3' 134.45(19) . . ? C7A' C3A' C3' 106.56(18) . . ? N1' C7A' C7' 130.2(2) . . ? N1' C7A' C3A' 107.54(19) . . ? C7' C7A' C3A' 122.3(2) . . ? C7' C6' C5' 121.6(2) . . ? C6' C7' C7A' 117.3(2) . . ? C5' C4' C3A' 118.7(2) . . ? C4' C5' C6' 121.1(2) . . ? _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 24.91 _diffrn_measured_fraction_theta_full 0.878 _refine_diff_density_max 0.196 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.054 #===END