#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206864.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2206864 _space_group_IT_number 15 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _[local]_cod_cif_authors_sg_H-M 'C 2/c' loop_ _publ_author_name 'S. Selvanayagam' 'Mahesh S. Chandak' 'D. Velmurugan' 'K. Ravikumar' 'R. Raghunathan' _publ_section_title ; 3,3-Bis(1H-indol-3-yl)indolin-2-one ; _journal_coeditor_code BT6707 _journal_issue 10 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3122 _journal_page_last o3123 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C24 H17 N3 O' _chemical_formula_moiety 'C24 H17 N3 O' _chemical_formula_sum 'C24 H17 N3 O' _chemical_formula_weight 363.41 _chemical_name_systematic ; 3,3-Bis(1H-indol-3-yl)indolin-2-one ; _symmetry_cell_setting monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 125.8610(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 24.0578(12) _cell_length_b 10.2342(5) _cell_length_c 18.1597(9) _cell_measurement_reflns_used 9828 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.56 _cell_measurement_theta_min 2.48 _cell_volume 3623.6(3) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Bruker SMART APEX area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 20359 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.03 _diffrn_reflns_theta_min 2.09 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 1520 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.305 _refine_diff_density_min -0.216 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 4278 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0496 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0696P)^2^+1.8470P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1284 _refine_ls_wR_factor_ref 0.1344 _reflns_number_gt 3677 _reflns_number_total 4278 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6707.cif 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' 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 0.36680(6) 0.34810(10) 0.47802(8) 0.0527(3) Uani d . 1 O N1 0.19426(7) 0.10835(13) 0.42508(9) 0.0478(3) Uani d . 1 N H1 0.1786 0.1034 0.4572 0.057 Uiso calc R 1 H N2 0.49456(7) -0.01347(15) 0.60660(10) 0.0585(4) Uani d . 1 N H2 0.5370 -0.0108 0.6522 0.070 Uiso calc R 1 H N3 0.35915(7) 0.31588(11) 0.34777(9) 0.0442(3) Uani d . 1 N H3 0.3673 0.3948 0.3404 0.053 Uiso calc R 1 H C1 0.15557(8) 0.11366(14) 0.33255(11) 0.0421(3) Uani d . 1 C C2 0.08467(9) 0.11248(19) 0.26935(14) 0.0606(5) Uani d . 1 C H2A 0.0560 0.1068 0.2880 0.073 Uiso calc R 1 H C3 0.05800(9) 0.11981(18) 0.17889(14) 0.0613(5) Uani d . 1 C H3A 0.0107 0.1180 0.1356 0.074 Uiso calc R 1 H C4 0.10087(8) 0.12999(15) 0.15087(11) 0.0497(4) Uani d . 1 C H4 0.0816 0.1363 0.0892 0.060 Uiso calc R 1 H C5 0.17132(7) 0.13091(13) 0.21295(10) 0.0382(3) Uani d . 1 C H5 0.1992 0.1380 0.1933 0.046 Uiso calc R 1 H C6 0.20042(7) 0.12108(12) 0.30600(10) 0.0335(3) Uani d . 1 C C7 0.26870(7) 0.11893(12) 0.38898(9) 0.0320(3) Uani d . 1 C C8 0.26183(8) 0.11228(14) 0.45823(10) 0.0397(3) Uani d . 1 C H8 0.2982 0.1106 0.5196 0.048 Uiso calc R 1 H C9 0.45245(8) -0.11961(16) 0.58086(10) 0.0454(4) Uani d . 1 C C10 0.46520(9) -0.24451(19) 0.61847(12) 0.0602(5) Uani d . 1 C H10 0.5083 -0.2671 0.6698 0.072 Uiso calc R 1 H C11 0.41269(10) -0.33243(18) 0.57782(13) 0.0598(5) Uani d . 1 C H11 0.4203 -0.4164 0.6015 0.072 Uiso calc R 1 H C12 0.34805(9) -0.29896(15) 0.50172(12) 0.0517(4) Uani d . 1 C H12 0.3131 -0.3607 0.4756 0.062 Uiso calc R 1 H C13 0.33481(7) -0.17591(14) 0.46412(9) 0.0393(3) Uani d . 1 C H13 0.2913 -0.1548 0.4131 0.047 Uiso calc R 1 H C14 0.38741(7) -0.08311(13) 0.50346(9) 0.0344(3) Uani d . 1 C C15 0.39265(7) 0.05122(13) 0.48435(9) 0.0343(3) Uani d . 1 C C16 0.45856(8) 0.08765(17) 0.54850(11) 0.0502(4) Uani d . 1 C H16 0.4766 0.1698 0.5523 0.060 Uiso calc R 1 H C17 0.33740(7) 0.13018(12) 0.40370(9) 0.0316(3) Uani d . 1 C C18 0.35667(7) 0.27795(13) 0.41715(10) 0.0379(3) Uani d . 1 C C19 0.34700(7) 0.21277(13) 0.28932(9) 0.0358(3) Uani d . 1 C C20 0.34793(8) 0.21436(16) 0.21404(10) 0.0459(4) Uani d . 1 C H20 0.3555 0.2913 0.1939 0.055 Uiso calc R 1 H C21 0.33709(9) 0.09674(17) 0.16975(11) 0.0508(4) Uani d . 1 C H21 0.3378 0.0945 0.1192 0.061 Uiso calc R 1 H C22 0.32518(9) -0.01725(16) 0.19913(10) 0.0475(4) Uani d . 1 C H22 0.3181 -0.0950 0.1683 0.057 Uiso calc R 1 H C23 0.32362(7) -0.01674(13) 0.27478(9) 0.0380(3) Uani d . 1 C H23 0.3154 -0.0934 0.2945 0.046 Uiso calc R 1 H C24 0.33440(6) 0.09928(13) 0.31944(9) 0.0315(3) Uani d . 1 C loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0733(8) 0.0406(6) 0.0699(7) -0.0152(5) 0.0562(7) -0.0197(5) N1 0.0508(7) 0.0574(8) 0.0560(8) 0.0045(6) 0.0429(7) 0.0089(6) N2 0.0322(6) 0.0699(10) 0.0507(8) -0.0035(6) 0.0116(6) 0.0013(7) N3 0.0614(8) 0.0298(6) 0.0571(8) -0.0066(5) 0.0435(7) -0.0011(5) C1 0.0430(8) 0.0380(7) 0.0562(9) 0.0056(6) 0.0352(7) 0.0106(6) C2 0.0409(8) 0.0711(12) 0.0782(12) 0.0112(8) 0.0396(9) 0.0283(9) C3 0.0344(8) 0.0641(11) 0.0722(12) 0.0063(7) 0.0238(8) 0.0257(9) C4 0.0457(8) 0.0438(8) 0.0481(9) 0.0040(6) 0.0211(7) 0.0111(7) C5 0.0413(7) 0.0319(7) 0.0434(7) 0.0018(5) 0.0261(6) 0.0046(5) C6 0.0367(7) 0.0245(6) 0.0454(7) 0.0021(5) 0.0275(6) 0.0034(5) C7 0.0378(7) 0.0278(6) 0.0384(7) 0.0003(5) 0.0267(6) 0.0003(5) C8 0.0444(8) 0.0421(7) 0.0429(7) 0.0010(6) 0.0313(7) 0.0020(6) C9 0.0359(7) 0.0550(9) 0.0412(8) 0.0031(6) 0.0203(6) 0.0014(6) C10 0.0514(10) 0.0661(11) 0.0518(9) 0.0200(8) 0.0238(8) 0.0194(8) C11 0.0693(11) 0.0463(9) 0.0615(10) 0.0119(8) 0.0370(9) 0.0174(8) C12 0.0606(10) 0.0407(8) 0.0540(9) -0.0035(7) 0.0337(8) 0.0025(7) C13 0.0417(7) 0.0389(7) 0.0357(7) -0.0023(6) 0.0218(6) -0.0006(6) C14 0.0356(6) 0.0393(7) 0.0314(6) 0.0023(5) 0.0214(5) -0.0001(5) C15 0.0346(6) 0.0379(7) 0.0350(6) -0.0040(5) 0.0230(6) -0.0044(5) C16 0.0413(8) 0.0510(9) 0.0538(9) -0.0109(7) 0.0254(7) -0.0071(7) C17 0.0380(7) 0.0287(6) 0.0368(6) -0.0031(5) 0.0267(6) -0.0034(5) C18 0.0420(7) 0.0331(7) 0.0497(8) -0.0044(5) 0.0331(7) -0.0051(6) C19 0.0364(7) 0.0354(7) 0.0413(7) 0.0000(5) 0.0259(6) 0.0017(5) C20 0.0520(9) 0.0499(9) 0.0449(8) -0.0039(7) 0.0335(7) 0.0070(7) C21 0.0599(10) 0.0642(10) 0.0396(8) -0.0024(8) 0.0355(8) -0.0010(7) C22 0.0598(9) 0.0480(9) 0.0424(8) -0.0019(7) 0.0343(7) -0.0089(6) C23 0.0451(7) 0.0347(7) 0.0399(7) -0.0002(5) 0.0281(6) -0.0004(5) C24 0.0311(6) 0.0350(6) 0.0339(6) 0.0010(5) 0.0221(5) 0.0013(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C18 1.217(2) y N1 C1 1.364(2) ? N1 C8 1.3637(19) ? N1 H1 0.8600 ? N2 C16 1.365(2) ? N2 C9 1.367(2) ? N2 H2 0.8600 ? N3 C18 1.3526(18) ? N3 C19 1.4007(18) ? N3 H3 0.8600 ? C1 C2 1.390(2) ? C1 C6 1.4186(19) ? C2 C3 1.372(3) ? C2 H2A 0.9300 ? C3 C4 1.396(3) ? C3 H3A 0.9300 ? C4 C5 1.380(2) ? C4 H4 0.9300 ? C5 C6 1.403(2) ? C5 H5 0.9300 ? C6 C7 1.4384(19) ? C7 C8 1.3628(18) ? C7 C17 1.516(2) y C8 H8 0.9300 ? C9 C10 1.396(2) ? C9 C14 1.4096(19) ? C10 C11 1.363(3) ? C10 H10 0.9300 ? C11 C12 1.388(3) ? C11 H11 0.9300 ? C12 C13 1.378(2) ? C12 H12 0.9300 ? C13 C14 1.3980(19) ? C13 H13 0.9300 ? C14 C15 1.4415(19) ? C15 C16 1.359(2) ? C15 C17 1.511(2) y C16 H16 0.9300 ? C17 C24 1.5221(17) ? C17 C18 1.5585(18) ? C19 C20 1.380(2) ? C19 C24 1.3909(18) ? C20 C21 1.385(2) ? C20 H20 0.9300 ? C21 C22 1.381(2) ? C21 H21 0.9300 ? C22 C23 1.3961(19) ? C22 H22 0.9300 ? C23 C24 1.3743(18) ? C23 H23 0.9300 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 C8 108.63(12) C1 N1 H1 125.7 C8 N1 H1 125.7 C16 N2 C9 109.30(13) C16 N2 H2 125.4 C9 N2 H2 125.4 C18 N3 C19 112.72(11) C18 N3 H3 123.6 C19 N3 H3 123.6 N1 C1 C2 129.67(15) N1 C1 C6 108.35(13) C2 C1 C6 121.98(15) C3 C2 C1 118.36(15) C3 C2 H2A 120.8 C1 C2 H2A 120.8 C2 C3 C4 120.91(16) C2 C3 H3A 119.5 C4 C3 H3A 119.5 C5 C4 C3 121.24(16) C5 C4 H4 119.4 C3 C4 H4 119.4 C4 C5 C6 119.40(14) C4 C5 H5 120.3 C6 C5 H5 120.3 C5 C6 C1 118.08(13) C5 C6 C7 136.10(12) C1 C6 C7 105.80(12) C8 C7 C6 106.63(12) C8 C7 C17 123.37(12) C6 C7 C17 129.90(11) C7 C8 N1 110.59(13) C7 C8 H8 124.7 N1 C8 H8 124.7 N2 C9 C10 130.82(15) N2 C9 C14 107.32(14) C10 C9 C14 121.86(15) C11 C10 C9 118.11(15) C11 C10 H10 120.9 C9 C10 H10 120.9 C10 C11 C12 121.24(16) C10 C11 H11 119.4 C12 C11 H11 119.4 C13 C12 C11 121.18(16) C13 C12 H12 119.4 C11 C12 H12 119.4 C12 C13 C14 119.37(14) C12 C13 H13 120.3 C14 C13 H13 120.3 C13 C14 C9 118.25(13) C13 C14 C15 134.88(13) C9 C14 C15 106.87(12) C16 C15 C14 106.15(13) C16 C15 C17 127.32(13) C14 C15 C17 126.29(11) C15 C16 N2 110.37(14) C15 C16 H16 124.8 N2 C16 H16 124.8 C15 C17 C7 112.29(10) C15 C17 C24 111.10(10) C7 C17 C24 113.71(11) C15 C17 C18 110.79(11) C7 C17 C18 107.14(10) C24 C17 C18 101.17(10) O1 C18 N3 125.60(13) O1 C18 C17 126.71(13) N3 C18 C17 107.69(11) C20 C19 C24 122.21(13) C20 C19 N3 128.64(13) C24 C19 N3 109.14(12) C19 C20 C21 117.26(13) C19 C20 H20 121.4 C21 C20 H20 121.4 C22 C21 C20 121.41(13) C22 C21 H21 119.3 C20 C21 H21 119.3 C21 C22 C23 120.55(14) C21 C22 H22 119.7 C23 C22 H22 119.7 C24 C23 C22 118.65(13) C24 C23 H23 120.7 C22 C23 H23 120.7 C23 C24 C19 119.91(12) C23 C24 C17 130.86(12) C19 C24 C17 109.21(11) 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_publ_flag C8 N1 C1 C2 -179.99(16) ? C8 N1 C1 C6 0.08(16) ? N1 C1 C2 C3 179.55(16) ? C6 C1 C2 C3 -0.5(3) ? C1 C2 C3 C4 -0.8(3) ? C2 C3 C4 C5 1.0(3) ? C3 C4 C5 C6 0.2(2) ? C4 C5 C6 C1 -1.48(19) ? C4 C5 C6 C7 -179.76(14) ? N1 C1 C6 C5 -178.37(12) ? C2 C1 C6 C5 1.7(2) ? N1 C1 C6 C7 0.39(15) ? C2 C1 C6 C7 -179.55(14) ? C5 C6 C7 C8 177.71(14) ? C1 C6 C7 C8 -0.71(14) ? C5 C6 C7 C17 1.4(2) ? C1 C6 C7 C17 -177.02(12) ? C6 C7 C8 N1 0.79(16) ? C17 C7 C8 N1 177.40(12) ? C1 N1 C8 C7 -0.55(17) ? C16 N2 C9 C10 -179.75(18) ? C16 N2 C9 C14 -0.05(19) ? N2 C9 C10 C11 -179.91(18) ? C14 C9 C10 C11 0.4(3) ? C9 C10 C11 C12 -0.7(3) ? C10 C11 C12 C13 0.5(3) ? C11 C12 C13 C14 -0.1(2) ? C12 C13 C14 C9 -0.1(2) ? C12 C13 C14 C15 -179.42(15) ? N2 C9 C14 C13 -179.78(13) ? C10 C9 C14 C13 0.0(2) ? N2 C9 C14 C15 -0.29(16) ? C10 C9 C14 C15 179.44(15) ? C13 C14 C15 C16 179.88(15) ? C9 C14 C15 C16 0.52(15) ? C13 C14 C15 C17 -5.4(2) ? C9 C14 C15 C17 175.26(12) ? C14 C15 C16 N2 -0.56(17) ? C17 C15 C16 N2 -175.23(13) ? C9 N2 C16 C15 0.4(2) ? C16 C15 C17 C7 -137.91(14) ? C14 C15 C17 C7 48.44(17) ? C16 C15 C17 C24 93.5(2) y C14 C15 C17 C24 -80.16(15) ? C16 C15 C17 C18 -18.15(19) ? C14 C15 C17 C18 168.21(12) ? C8 C7 C17 C15 37.08(17) ? C6 C7 C17 C15 -147.15(13) ? C8 C7 C17 C24 164.30(10) y C6 C7 C17 C24 -19.93(18) ? C8 C7 C17 C18 -84.79(15) ? C6 C7 C17 C18 90.98(15) ? C19 N3 C18 O1 178.41(14) ? C19 N3 C18 C17 -2.54(16) ? C15 C17 C18 O1 -60.28(18) ? C7 C17 C18 O1 62.52(19) ? C24 C17 C18 O1 -178.16(15) ? C15 C17 C18 N3 120.68(12) ? C7 C17 C18 N3 -116.51(12) ? C24 C17 C18 N3 2.81(14) ? C18 N3 C19 C20 -177.52(15) ? C18 N3 C19 C24 1.10(17) ? C24 C19 C20 C21 -1.3(2) ? N3 C19 C20 C21 177.16(15) ? C19 C20 C21 C22 0.6(2) ? C20 C21 C22 C23 0.1(3) ? C21 C22 C23 C24 -0.2(2) ? C22 C23 C24 C19 -0.4(2) ? C22 C23 C24 C17 -178.43(14) ? C20 C19 C24 C23 1.2(2) ? N3 C19 C24 C23 -177.49(12) ? C20 C19 C24 C17 179.62(13) ? N3 C19 C24 C17 0.90(15) ? C15 C17 C24 C23 58.30(18) ? C7 C17 C24 C23 -69.54(18) ? C18 C17 C24 C23 175.95(14) ? C15 C17 C24 C19 -119.85(12) ? C7 C17 C24 C19 112.30(12) ? C18 C17 C24 C19 -2.20(14) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1 O1 7_556 0.86 2.08 2.913(2) 162 _cod_database_code 2206864