#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/23/2202399.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_2202399 loop_ _publ_author_name 'M. M. Govind' 'S. Selvanayagam' 'D. Velmurugan' 'K. Ravikumar' 'Gowri Sridhar' 'R. Raghunathan' _publ_section_title 5''-Benzylidene-1'-methyl-4'-phenylindole-3-spiro-2'-pyrrolidine-3'-spiro-3''-piperidine-2(3H),4''-dione _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1878 _journal_page_last o1880 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C30 H29 N3 O2' _chemical_formula_moiety 'C30 H29 N3 O2' _chemical_formula_sum 'C30 H29 N3 O2' _chemical_formula_weight 463.56 _chemical_name_systematic ;5''-Benzylidene-1'-methyl-4'-phenylindole-3-spiro-2'-pyrrolidine-3'-spiro-3''- piperidine-2(3H),4''-dione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _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 95.2830(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.6889(7) _cell_length_b 18.9025(12) _cell_length_c 12.5270(8) _cell_measurement_reflns_used 2146 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20.39 _cell_measurement_theta_min 2.39 _cell_volume 2520.3(3) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction SAINT _computing_molecular_graphics ; ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990) ; _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 0.967 _diffrn_measured_fraction_theta_max 0.915 _diffrn_measurement_device 'Bruker SMART APEX area-detector' _diffrn_measurement_device_type 'CCD 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 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 15727 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 1.96 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 984 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.250 _refine_diff_density_min -0.153 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 316 _refine_ls_number_reflns 5738 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.991 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0526 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0826P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1300 _refine_ls_wR_factor_ref 0.1480 _reflns_number_gt 3798 _reflns_number_total 5738 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6370.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_angle_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2202399 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' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.48578(12) 0.05034(8) 0.13101(11) 0.0415(4) Uani d . 1 . . N H1 0.4284 0.0308 0.0882 0.050 Uiso calc R 1 . . H C2 0.46189(15) 0.09039(9) 0.22118(13) 0.0380(4) Uani d . 1 . . C C3 0.34809(16) 0.10568(10) 0.25845(15) 0.0489(5) Uani d . 1 . . C H3 0.2729 0.0920 0.2209 0.059 Uiso calc R 1 . . H C4 0.35009(19) 0.14222(12) 0.35403(17) 0.0609(6) Uani d . 1 . . C H4 0.2744 0.1538 0.3807 0.073 Uiso calc R 1 . . H C5 0.46088(19) 0.16194(12) 0.41093(17) 0.0588(5) Uani d . 1 . . C H5 0.4592 0.1860 0.4756 0.071 Uiso calc R 1 . . H C6 0.57489(17) 0.14610(10) 0.37227(14) 0.0468(4) Uani d . 1 . . C H6 0.6500 0.1587 0.4110 0.056 Uiso calc R 1 . . H C7 0.57542(15) 0.11133(9) 0.27529(13) 0.0364(4) Uani d . 1 . . C C8 0.68287(14) 0.08674(9) 0.21422(13) 0.0364(4) Uani d . 1 . . C C9 0.61006(15) 0.04616(9) 0.11963(13) 0.0394(4) Uani d . 1 . . C N10 0.76906(13) 0.04031(8) 0.27999(11) 0.0429(4) Uani d . 1 . . N C11 0.88892(15) 0.04145(10) 0.23388(15) 0.0468(5) Uani d . 1 . . C H11A 0.8848 0.0156 0.1667 0.056 Uiso calc R 1 . . H H11B 0.9556 0.0219 0.2829 0.056 Uiso calc R 1 . . H C12 0.90743(14) 0.11982(9) 0.21664(13) 0.0387(4) Uani d . 1 . . C H12 0.9259 0.1410 0.2877 0.046 Uiso calc R 1 . . H C13 0.77340(14) 0.14584(9) 0.17336(13) 0.0348(4) Uani d . 1 . . C C14 1.01211(15) 0.14221(10) 0.15007(14) 0.0408(4) Uani d . 1 . . C C15 1.06749(17) 0.20810(10) 0.16772(16) 0.0511(5) Uani d . 1 . . C H15 1.0402 0.2373 0.2207 0.061 Uiso calc R 1 . . H C16 1.1621(2) 0.23136(12) 0.10851(18) 0.0613(6) Uani d . 1 . . C H16 1.1973 0.2759 0.1214 0.074 Uiso calc R 1 . . H C17 1.2040(2) 0.18905(14) 0.03097(18) 0.0648(6) Uani d . 1 . . C H17 1.2679 0.2046 -0.0089 0.078 Uiso calc R 1 . . H C18 1.15167(18) 0.12389(13) 0.01214(16) 0.0622(6) Uani d . 1 . . C H18 1.1801 0.0950 -0.0406 0.075 Uiso calc R 1 . . H C19 1.05615(17) 0.10046(11) 0.07138(15) 0.0525(5) Uani d . 1 . . C H19 1.0213 0.0559 0.0578 0.063 Uiso calc R 1 . . H C20 0.75705(14) 0.15373(9) 0.05112(13) 0.0395(4) Uani d . 1 . . C H20A 0.8101 0.1916 0.0289 0.047 Uiso calc R 1 . . H H20B 0.7810 0.1102 0.0173 0.047 Uiso calc R 1 . . H N21 0.62564(12) 0.16966(8) 0.01937(10) 0.0394(3) Uani d . 1 . . N C22 0.59718(17) 0.24224(9) 0.04656(14) 0.0430(4) Uani d . 1 . . C H22A 0.5074 0.2501 0.0329 0.052 Uiso calc R 1 . . H H22B 0.6393 0.2740 0.0007 0.052 Uiso calc R 1 . . H C23 0.63742(15) 0.25949(9) 0.16199(13) 0.0377(4) Uani d . 1 . . C C24 0.74271(15) 0.21831(9) 0.21959(13) 0.0370(4) Uani d . 1 . . C C25 0.58269(16) 0.30882(9) 0.21864(14) 0.0422(4) Uani d . 1 . . C H25 0.6146 0.3130 0.2900 0.051 Uiso calc R 1 . . H C26 0.47978(16) 0.35719(9) 0.18434(14) 0.0419(4) Uani d . 1 . . C C27 0.4547(2) 0.38209(10) 0.08044(16) 0.0568(5) Uani d . 1 . . C H27 0.5054 0.3678 0.0279 0.068 Uiso calc R 1 . . H C28 0.3560(2) 0.42775(12) 0.05358(19) 0.0702(7) Uani d . 1 . . C H28 0.3397 0.4431 -0.0169 0.084 Uiso calc R 1 . . H C29 0.2820(2) 0.45048(12) 0.1303(2) 0.0746(7) Uani d . 1 . . C H29 0.2148 0.4807 0.1119 0.089 Uiso calc R 1 . . H C30 0.3074(2) 0.42850(12) 0.2343(2) 0.0700(6) Uani d . 1 . . C H30 0.2588 0.4449 0.2870 0.084 Uiso calc R 1 . . H C31 0.40445(19) 0.38222(11) 0.26091(17) 0.0561(5) Uani d . 1 . . C H31 0.4201 0.3673 0.3316 0.067 Uiso calc R 1 . . H O32 0.65823(11) 0.01101(7) 0.05185(10) 0.0491(3) Uani d . 1 . . O C33 0.71957(19) -0.02955(11) 0.30353(18) 0.0598(5) Uani d . 1 . . C H33A 0.6405 -0.0243 0.3334 0.090 Uiso calc R 1 . . H H33B 0.7779 -0.0535 0.3540 0.090 Uiso calc R 1 . . H H33C 0.7078 -0.0567 0.2386 0.090 Uiso calc R 1 . . H C34 0.58851(19) 0.15563(11) -0.09321(15) 0.0557(5) Uani d . 1 . . C H34A 0.6088 0.1076 -0.1096 0.084 Uiso calc R 1 . . H H34B 0.6326 0.1872 -0.1367 0.084 Uiso calc R 1 . . H H34C 0.4997 0.1628 -0.1076 0.084 Uiso calc R 1 . . H O35 0.80183(11) 0.24174(7) 0.29905(10) 0.0513(3) Uani d . 1 . . O 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 N1 0.0339(7) 0.0455(9) 0.0435(8) -0.0055(6) -0.0051(6) -0.0087(6) C2 0.0374(9) 0.0363(9) 0.0396(9) -0.0018(7) -0.0006(7) -0.0006(7) C3 0.0352(9) 0.0580(12) 0.0529(12) -0.0006(8) 0.0020(8) 0.0008(9) C4 0.0475(11) 0.0761(15) 0.0611(14) 0.0052(10) 0.0158(10) -0.0062(11) C5 0.0589(12) 0.0695(14) 0.0494(12) 0.0011(10) 0.0118(10) -0.0147(10) C6 0.0441(10) 0.0542(12) 0.0415(10) -0.0017(8) 0.0012(8) -0.0078(8) C7 0.0359(8) 0.0361(9) 0.0369(9) 0.0011(7) 0.0017(7) -0.0010(7) C8 0.0339(8) 0.0371(9) 0.0369(9) 0.0019(7) -0.0034(7) -0.0046(7) C9 0.0388(9) 0.0359(9) 0.0423(10) 0.0004(7) -0.0036(7) -0.0050(7) N10 0.0373(8) 0.0427(8) 0.0473(9) 0.0037(6) -0.0034(6) 0.0033(6) C11 0.0367(9) 0.0487(11) 0.0530(11) 0.0097(8) -0.0059(8) -0.0030(8) C12 0.0316(8) 0.0455(10) 0.0379(9) 0.0038(7) -0.0035(7) -0.0072(7) C13 0.0285(8) 0.0394(9) 0.0358(9) 0.0020(6) -0.0013(7) -0.0057(7) C14 0.0287(8) 0.0516(11) 0.0404(10) 0.0046(7) -0.0055(7) -0.0063(8) C15 0.0428(10) 0.0535(12) 0.0558(12) 0.0000(9) -0.0009(9) -0.0082(9) C16 0.0529(12) 0.0614(14) 0.0687(15) -0.0084(10) 0.0012(11) 0.0082(11) C17 0.0481(12) 0.0900(18) 0.0566(13) 0.0012(12) 0.0059(10) 0.0177(12) C18 0.0501(12) 0.0885(17) 0.0485(12) 0.0131(11) 0.0079(9) -0.0079(11) C19 0.0446(10) 0.0599(13) 0.0521(12) 0.0034(9) -0.0001(9) -0.0126(9) C20 0.0359(9) 0.0438(10) 0.0384(10) 0.0035(7) 0.0019(7) -0.0053(7) N21 0.0373(7) 0.0440(8) 0.0355(8) 0.0049(6) -0.0041(6) -0.0056(6) C22 0.0405(9) 0.0437(10) 0.0439(10) 0.0058(8) 0.0001(8) 0.0021(8) C23 0.0355(9) 0.0358(9) 0.0411(10) -0.0006(7) 0.0003(7) -0.0015(7) C24 0.0343(8) 0.0397(9) 0.0370(9) -0.0023(7) 0.0029(7) -0.0047(7) C25 0.0459(10) 0.0397(10) 0.0407(10) 0.0013(8) 0.0019(8) -0.0016(7) C26 0.0433(9) 0.0354(9) 0.0468(11) 0.0023(7) 0.0030(8) -0.0034(7) C27 0.0709(13) 0.0492(12) 0.0499(12) 0.0147(10) 0.0031(10) -0.0035(9) C28 0.0878(17) 0.0568(14) 0.0620(14) 0.0223(12) -0.0141(12) -0.0028(10) C29 0.0609(14) 0.0572(14) 0.104(2) 0.0205(11) -0.0031(13) 0.0000(13) C30 0.0627(14) 0.0599(14) 0.0912(18) 0.0163(11) 0.0279(13) 0.0057(12) C31 0.0625(12) 0.0487(12) 0.0595(13) 0.0098(10) 0.0177(10) 0.0064(9) O32 0.0460(7) 0.0500(8) 0.0502(8) 0.0043(6) -0.0023(6) -0.0203(6) C33 0.0576(12) 0.0484(12) 0.0720(14) 0.0025(9) -0.0015(10) 0.0122(10) C34 0.0598(12) 0.0637(13) 0.0411(11) 0.0111(10) -0.0092(9) -0.0073(9) O35 0.0450(7) 0.0541(8) 0.0520(8) 0.0059(6) -0.0097(6) -0.0190(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C9 . 1.351(2) ? N1 C2 . 1.403(2) ? N1 H1 . 0.8600 ? C2 C3 . 1.373(2) ? C2 C7 . 1.392(2) ? C3 C4 . 1.381(3) ? C3 H3 . 0.9300 ? C4 C5 . 1.376(3) ? C4 H4 . 0.9300 ? C5 C6 . 1.385(3) ? C5 H5 . 0.9300 ? C6 C7 . 1.382(2) ? C6 H6 . 0.9300 ? C7 C8 . 1.511(2) ? C8 N10 . 1.469(2) ? C8 C9 . 1.558(2) ? C8 C13 . 1.593(2) ? C9 O32 . 1.2280(19) ? N10 C11 . 1.453(2) y N10 C33 . 1.463(2) y C11 C12 . 1.513(2) ? C11 H11A . 0.9700 ? C11 H11B . 0.9700 ? C12 C14 . 1.516(2) ? C12 C13 . 1.564(2) ? C12 H12 . 0.9800 ? C13 C20 . 1.532(2) ? C13 C24 . 1.534(2) ? C14 C19 . 1.379(2) ? C14 C15 . 1.388(2) ? C15 C16 . 1.380(3) ? C15 H15 . 0.9300 ? C16 C17 . 1.365(3) ? C16 H16 . 0.9300 ? C17 C18 . 1.364(3) ? C17 H17 . 0.9300 ? C18 C19 . 1.389(3) ? C18 H18 . 0.9300 ? C19 H19 . 0.9300 ? C20 N21 . 1.4557(19) ? C20 H20A . 0.9700 ? C20 H20B . 0.9700 ? N21 C22 . 1.453(2) ? N21 C34 . 1.454(2) ? C22 C23 . 1.506(2) ? C22 H22A . 0.9700 ? C22 H22B . 0.9700 ? C23 C25 . 1.339(2) ? C23 C24 . 1.498(2) ? C24 O35 . 1.2126(19) ? C25 C26 . 1.464(2) ? C25 H25 . 0.9300 ? C26 C27 . 1.387(3) ? C26 C31 . 1.391(3) ? C27 C28 . 1.381(3) ? C27 H27 . 0.9300 ? C28 C29 . 1.368(3) ? C28 H28 . 0.9300 ? C29 C30 . 1.371(3) ? C29 H29 . 0.9300 ? C30 C31 . 1.374(3) ? C30 H30 . 0.9300 ? C31 H31 . 0.9300 ? C33 H33A . 0.9600 ? C33 H33B . 0.9600 ? C33 H33C . 0.9600 ? C34 H34A . 0.9600 ? C34 H34B . 0.9600 ? C34 H34C . 0.9600 ? 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C9 N1 C2 111.70(10) y C9 N1 H1 124.1 y C2 N1 H1 124.1 y C3 C2 C7 122.31(16) ? C3 C2 N1 128.32(15) ? C7 C2 N1 109.30(14) ? C2 C3 C4 117.17(17) ? C2 C3 H3 121.4 ? C4 C3 H3 121.4 ? C5 C4 C3 121.91(18) ? C5 C4 H4 119.0 ? C3 C4 H4 119.0 ? C4 C5 C6 120.21(19) ? C4 C5 H5 119.9 ? C6 C5 H5 119.9 ? C7 C6 C5 119.03(17) ? C7 C6 H6 120.5 ? C5 C6 H6 120.5 ? C6 C7 C2 119.31(15) ? C6 C7 C8 131.03(15) ? C2 C7 C8 109.59(14) ? N10 C8 C7 111.51(13) ? N10 C8 C9 112.07(13) ? C7 C8 C9 100.76(12) ? N10 C8 C13 103.36(12) ? C7 C8 C13 117.37(13) ? C9 C8 C13 112.12(13) ? O32 C9 N1 125.69(15) ? O32 C9 C8 125.47(14) ? N1 C9 C8 108.54(14) ? C11 N10 C33 116.2(2) y C11 N10 C8 107.40(10) y C33 N10 C8 115.60(10) y N10 C11 C12 101.72(13) ? N10 C11 H11A 111.4 ? C12 C11 H11A 111.4 ? N10 C11 H11B 111.4 ? C12 C11 H11B 111.4 ? H11A C11 H11B 109.3 ? C11 C12 C14 117.70(14) ? C11 C12 C13 103.29(13) ? C14 C12 C13 114.87(13) ? C11 C12 H12 106.8 ? C14 C12 H12 106.8 ? C13 C12 H12 106.8 ? C20 C13 C24 106.35(13) ? C20 C13 C12 113.18(13) ? C24 C13 C12 111.77(12) ? C20 C13 C8 111.88(12) ? C24 C13 C8 110.33(13) ? C12 C13 C8 103.43(12) ? C19 C14 C15 117.31(17) ? C19 C14 C12 123.45(17) ? C15 C14 C12 119.24(15) ? C16 C15 C14 121.54(19) ? C16 C15 H15 119.2 ? C14 C15 H15 119.2 ? C17 C16 C15 120.0(2) ? C17 C16 H16 120.0 ? C15 C16 H16 120.0 ? C18 C17 C16 119.7(2) ? C18 C17 H17 120.1 ? C16 C17 H17 120.1 ? C17 C18 C19 120.4(2) ? C17 C18 H18 119.8 ? C19 C18 H18 119.8 ? C14 C19 C18 121.0(2) ? C14 C19 H19 119.5 ? C18 C19 H19 119.5 ? N21 C20 C13 108.15(13) ? N21 C20 H20A 110.1 ? C13 C20 H20A 110.1 ? N21 C20 H20B 110.1 ? C13 C20 H20B 110.1 ? H20A C20 H20B 108.4 ? C22 N21 C34 110.82(13) ? C22 N21 C20 110.42(13) ? C34 N21 C20 113.43(14) ? N21 C22 C23 112.47(13) ? N21 C22 H22A 109.1 ? C23 C22 H22A 109.1 ? N21 C22 H22B 109.1 ? C23 C22 H22B 109.1 ? H22A C22 H22B 107.8 ? C25 C23 C24 116.89(15) ? C25 C23 C22 124.05(15) ? C24 C23 C22 119.05(14) ? O35 C24 C23 121.16(15) ? O35 C24 C13 121.49(15) ? C23 C24 C13 117.35(13) ? C23 C25 C26 129.24(16) ? C23 C25 H25 115.4 ? C26 C25 H25 115.4 ? C27 C26 C31 117.24(17) ? C27 C26 C25 124.21(16) ? C31 C26 C25 118.50(16) ? C28 C27 C26 121.20(19) ? C28 C27 H27 119.4 ? C26 C27 H27 119.4 ? C29 C28 C27 120.2(2) ? C29 C28 H28 119.9 ? C27 C28 H28 119.9 ? C28 C29 C30 119.7(2) ? C28 C29 H29 120.1 ? C30 C29 H29 120.1 ? C29 C30 C31 120.1(2) ? C29 C30 H30 119.9 ? C31 C30 H30 119.9 ? C30 C31 C26 121.4(2) ? C30 C31 H31 119.3 ? C26 C31 H31 119.3 ? N10 C33 H33A 109.5 ? N10 C33 H33B 109.5 ? H33A C33 H33B 109.5 ? N10 C33 H33C 109.5 ? H33A C33 H33C 109.5 ? H33B C33 H33C 109.5 ? N21 C34 H34A 109.5 ? N21 C34 H34B 109.5 ? H34A C34 H34B 109.5 ? N21 C34 H34C 109.5 ? H34A C34 H34C 109.5 ? H34B C34 H34C 109.5 ? 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 C12 H12 O35 . 0.98 2.33 2.804(2) 109 C20 H20B O32 . 0.97 2.35 2.898(2) 115 C25 H25 O35 . 0.93 2.41 2.770(2) 103 N1 H1 O32 3_655 0.86 2.06 2.883(2) 159 C28 H28 N10 4_565 0.93 2.61 3.520(3) 168 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 C9 N1 C2 C3 -179.57(18) ? C9 N1 C2 C7 -2.7(2) ? C7 C2 C3 C4 -1.0(3) ? N1 C2 C3 C4 175.45(18) ? C2 C3 C4 C5 -0.8(3) ? C3 C4 C5 C6 0.8(3) ? C4 C5 C6 C7 1.0(3) ? C5 C6 C7 C2 -2.8(3) ? C5 C6 C7 C8 -179.31(18) ? C3 C2 C7 C6 2.8(3) ? N1 C2 C7 C6 -174.22(15) ? C3 C2 C7 C8 -179.93(16) ? N1 C2 C7 C8 3.01(19) ? C6 C7 C8 N10 55.6(2) ? C2 C7 C8 N10 -121.19(15) ? C6 C7 C8 C9 174.70(18) ? C2 C7 C8 C9 -2.11(17) ? C6 C7 C8 C13 -63.3(2) ? C2 C7 C8 C13 119.89(15) ? C2 N1 C9 O32 175.26(17) ? C2 N1 C9 C8 1.29(19) ? N10 C8 C9 O32 -54.8(2) ? C7 C8 C9 O32 -173.49(17) ? C13 C8 C9 O32 60.9(2) ? N10 C8 C9 N1 119.16(15) ? C7 C8 C9 N1 0.50(17) ? C13 C8 C9 N1 -125.12(14) ? C7 C8 N10 C11 -158.55(13) ? C9 C8 N10 C11 89.34(16) ? C13 C8 N10 C11 -31.58(16) ? C7 C8 N10 C33 69.85(19) ? C9 C8 N10 C33 -42.3(2) ? C13 C8 N10 C33 -163.18(14) ? C33 N10 C11 C12 177.85(14) ? C8 N10 C11 C12 46.58(16) ? N10 C11 C12 C14 -168.91(13) ? N10 C11 C12 C13 -41.18(16) ? C11 C12 C13 C20 -99.21(16) ? C14 C12 C13 C20 30.27(19) ? C11 C12 C13 C24 140.74(14) ? C14 C12 C13 C24 -89.77(17) ? C11 C12 C13 C8 22.05(16) ? C14 C12 C13 C8 151.54(14) ? N10 C8 C13 C20 126.76(13) ? C7 C8 C13 C20 -110.06(15) ? C9 C8 C13 C20 5.87(17) ? N10 C8 C13 C24 -115.05(13) ? C7 C8 C13 C24 8.12(18) ? C9 C8 C13 C24 124.06(14) ? N10 C8 C13 C12 4.63(15) ? C7 C8 C13 C12 127.80(13) ? C9 C8 C13 C12 -116.27(13) ? C11 C12 C14 C19 27.2(2) y C13 C12 C14 C19 -94.7(2) ? C11 C12 C14 C15 -153.02(16) ? C13 C12 C14 C15 85.01(19) ? C19 C14 C15 C16 0.5(3) ? C12 C14 C15 C16 -179.23(16) ? C14 C15 C16 C17 -0.5(3) ? C15 C16 C17 C18 0.2(3) ? C16 C17 C18 C19 0.0(3) ? C15 C14 C19 C18 -0.3(3) ? C12 C14 C19 C18 179.45(16) ? C17 C18 C19 C14 0.0(3) ? C24 C13 C20 N21 -63.73(16) ? C12 C13 C20 N21 173.18(13) ? C8 C13 C20 N21 56.81(17) ? C13 C20 N21 C22 74.10(17) ? C13 C20 N21 C34 -160.82(15) ? C34 N21 C22 C23 -178.47(15) ? C20 N21 C22 C23 -51.93(19) ? N21 C22 C23 C25 -152.55(17) ? N21 C22 C23 C24 25.7(2) ? C25 C23 C24 O35 -22.8(2) ? C22 C23 C24 O35 158.76(16) ? C25 C23 C24 C13 157.76(15) ? C22 C23 C24 C13 -20.6(2) ? C20 C13 C24 O35 -141.51(16) ? C12 C13 C24 O35 -17.5(2) ? C8 C13 C24 O35 96.96(18) ? C20 C13 C24 C23 37.87(18) ? C12 C13 C24 C23 161.85(14) ? C8 C13 C24 C23 -83.65(17) ? C24 C23 C25 C26 179.34(16) ? C22 C23 C25 C26 -2.4(3) ? C23 C25 C26 C27 -28.9(3) ? C23 C25 C26 C31 153.63(19) ? C31 C26 C27 C28 -2.4(3) ? C25 C26 C27 C28 -179.94(19) ? C26 C27 C28 C29 1.3(3) ? C27 C28 C29 C30 0.9(4) ? C28 C29 C30 C31 -1.9(4) ? C29 C30 C31 C26 0.7(3) ? C27 C26 C31 C30 1.4(3) ? C25 C26 C31 C30 179.10(19) ?