#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2202406.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_2202406 loop_ _publ_author_name 'Seshadri, P. R.' 'Selvanayagam, S.' 'Velmurugan, D.' 'Ravikumar, K.' 'Sureshbabu, A. R.' 'Raghunathan, R.' _publ_section_title ; 1-Methyl-4'-(3-nitrophenyl)-1H-indole-3-spiro-2'-pyrrolidine-3'-spiro-2''-indan-2,1'',3''-trione ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2025 _journal_page_last o2027 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C26 H19 N3 O5' _chemical_formula_moiety 'C26 H19 N3 O5' _chemical_formula_sum 'C26 H19 N3 O5' _chemical_formula_weight 453.44 _chemical_name_systematic ; 1-Methyl-4'-(3-nitrophenyl)-1H-indole-3-spiro-2'-pyrrolidine-3'- spiro-2''-indan-2,1'',3''-trione ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 93.392(2) _cell_angle_beta 91.0920(10) _cell_angle_gamma 93.6600(10) _cell_formula_units_Z 2 _cell_length_a 7.7610(6) _cell_length_b 11.6696(10) _cell_length_c 11.9952(9) _cell_measurement_reflns_used 2386 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.15 _cell_measurement_theta_min 2.37 _cell_volume 1081.98(15) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001) ' _computing_data_reduction SAINT _computing_molecular_graphics ; 'ORTEP3 (Farrugia, 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 0.909 _diffrn_measured_fraction_theta_max 0.909 _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_method '\w scans' _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 0.0135 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 6822 _diffrn_reflns_theta_full 27.98 _diffrn_reflns_theta_max 27.98 _diffrn_reflns_theta_min 1.75 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_T_max 0.9864 _exptl_absorpt_correction_T_min 0.9796 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2001)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Needles _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.307 _refine_diff_density_min -0.258 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 4747 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.014 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0519 _refine_ls_shift/su_max <0.000 _refine_ls_shift/su_mean <0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0932P)^2^+0.165P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1465 _refine_ls_wR_factor_ref 0.1627 _reflns_number_gt 3472 _reflns_number_total 4747 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6378.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 2202406 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 N1 0.0636(2) 0.02827(15) 0.14814(14) 0.0613(5) Uani d . 1 N H1 -0.0160 -0.0161 0.1142 0.074 Uiso calc R 1 H C2 0.1514(3) 0.11612(18) 0.10045(17) 0.0560(5) Uani d . 1 C O3 0.1462(2) 0.13715(14) 0.00201(12) 0.0722(5) Uani d . 1 O C4 0.2656(2) 0.18439(16) 0.19517(14) 0.0465(4) Uani d . 1 C C5 0.2429(2) 0.10601(15) 0.28967(15) 0.0454(4) Uani d . 1 C C6 0.3245(2) 0.10738(16) 0.39291(17) 0.0527(5) Uani d . 1 C H6 0.4108 0.1640 0.4137 0.063 Uiso calc R 1 H C7 0.2763(3) 0.02350(18) 0.46520(18) 0.0605(5) Uani d . 1 C H7 0.3303 0.0239 0.5351 0.073 Uiso calc R 1 H C8 0.1484(3) -0.06093(18) 0.4342(2) 0.0644(6) Uani d . 1 C H8 0.1161 -0.1157 0.4844 0.077 Uiso calc R 1 H C9 0.0678(3) -0.06564(17) 0.33022(19) 0.0620(5) Uani d . 1 C H9 -0.0170 -0.1232 0.3091 0.074 Uiso calc R 1 H C10 0.1176(2) 0.01804(16) 0.25889(16) 0.0506(4) Uani d . 1 C C11 0.2000(2) 0.30860(15) 0.21580(14) 0.0435(4) Uani d . 1 C C12 0.2879(2) 0.37348(17) 0.12103(15) 0.0498(4) Uani d . 1 C H12 0.2127 0.3581 0.0546 0.060 Uiso calc R 1 H C13 0.4519(3) 0.31045(19) 0.09801(19) 0.0652(6) Uani d . 1 C H13A 0.4559 0.2852 0.0197 0.078 Uiso calc R 1 H H13B 0.5538 0.3607 0.1173 0.078 Uiso calc R 1 H N14 0.44401(19) 0.21205(13) 0.16730(13) 0.0500(4) Uani d . 1 N C15 0.5400(3) 0.1160(2) 0.1256(2) 0.0767(7) Uani d . 1 C H15A 0.5282 0.0550 0.1758 0.115 Uiso calc R 1 H H15B 0.6598 0.1408 0.1206 0.115 Uiso calc R 1 H H15C 0.4954 0.0889 0.0530 0.115 Uiso calc R 1 H C16 0.3070(2) 0.50315(16) 0.14180(14) 0.0472(4) Uani d . 1 C C17 0.1677(3) 0.56849(19) 0.11844(16) 0.0567(5) Uani d . 1 C H17 0.0650 0.5311 0.0908 0.068 Uiso calc R 1 H C18 0.1773(3) 0.6870(2) 0.13506(18) 0.0649(5) Uani d . 1 C H18 0.0819 0.7278 0.1185 0.078 Uiso calc R 1 H C19 0.3270(3) 0.74446(19) 0.17598(18) 0.0646(6) Uani d . 1 C H19 0.3352 0.8241 0.1883 0.078 Uiso calc R 1 H C20 0.4643(3) 0.68013(18) 0.19809(16) 0.0586(5) Uani d . 1 C N21 0.6288(3) 0.7408(2) 0.23596(19) 0.0862(7) Uani d . 1 N O22 0.7586(3) 0.6863(2) 0.2372(2) 0.1137(8) Uani d . 1 O O23 0.6306(4) 0.8442(2) 0.2582(3) 0.1482(11) Uani d . 1 O C24 0.4578(3) 0.56196(18) 0.18234(16) 0.0561(5) Uani d . 1 C H24 0.5542 0.5221 0.1988 0.067 Uiso calc R 1 H C25 0.0016(2) 0.31102(16) 0.21594(15) 0.0483(4) Uani d . 1 C O26 -0.09065(18) 0.30536(16) 0.13356(12) 0.0714(5) Uani d . 1 O C27 -0.0520(2) 0.32635(15) 0.33292(15) 0.0459(4) Uani d . 1 C C28 -0.2186(3) 0.32476(18) 0.37410(18) 0.0579(5) Uani d . 1 C H28 -0.3153 0.3109 0.3270 0.069 Uiso calc R 1 H C29 -0.2339(3) 0.34456(19) 0.48762(19) 0.0647(6) Uani d . 1 C H29 -0.3433 0.3455 0.5178 0.078 Uiso calc R 1 H C30 -0.0903(3) 0.36305(18) 0.55766(17) 0.0620(5) Uani d . 1 C H30 -0.1056 0.3739 0.6342 0.074 Uiso calc R 1 H C31 0.0754(3) 0.36588(16) 0.51733(15) 0.0520(4) Uani d . 1 C H31 0.1714 0.3794 0.5649 0.062 Uiso calc R 1 H C32 0.0924(2) 0.34762(15) 0.40279(14) 0.0441(4) Uani d . 1 C C33 0.2507(2) 0.35300(14) 0.33584(14) 0.0412(4) Uani d . 1 C O34 0.39307(16) 0.38840(12) 0.36893(11) 0.0534(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 0.0585(10) 0.0641(10) 0.0556(10) -0.0203(8) -0.0027(7) -0.0167(8) C2 0.0564(11) 0.0596(12) 0.0483(10) -0.0072(9) -0.0011(8) -0.0149(8) O3 0.0861(11) 0.0806(11) 0.0447(8) -0.0177(8) -0.0061(7) -0.0126(7) C4 0.0441(9) 0.0506(10) 0.0421(9) -0.0051(7) 0.0009(7) -0.0107(7) C5 0.0421(9) 0.0410(9) 0.0512(10) -0.0021(7) 0.0019(7) -0.0080(7) C6 0.0475(10) 0.0491(10) 0.0601(11) -0.0002(8) -0.0059(8) -0.0027(8) C7 0.0646(12) 0.0580(12) 0.0598(12) 0.0097(9) -0.0034(9) 0.0050(9) C8 0.0715(14) 0.0496(11) 0.0726(14) 0.0042(10) 0.0138(11) 0.0033(10) C9 0.0609(12) 0.0488(11) 0.0732(14) -0.0101(9) 0.0122(10) -0.0095(10) C10 0.0459(10) 0.0485(10) 0.0550(11) -0.0038(8) 0.0042(8) -0.0126(8) C11 0.0408(9) 0.0498(9) 0.0383(8) -0.0032(7) 0.0002(6) -0.0036(7) C12 0.0508(10) 0.0585(11) 0.0387(9) -0.0041(8) 0.0023(7) -0.0006(8) C13 0.0666(13) 0.0662(13) 0.0630(13) 0.0032(10) 0.0252(10) 0.0001(10) N14 0.0458(8) 0.0477(8) 0.0546(9) -0.0022(6) 0.0095(7) -0.0103(7) C15 0.0667(14) 0.0587(13) 0.1022(18) 0.0031(10) 0.0252(13) -0.0224(12) C16 0.0487(10) 0.0573(11) 0.0351(8) -0.0028(8) 0.0027(7) 0.0044(7) C17 0.0505(11) 0.0714(13) 0.0474(10) -0.0001(9) -0.0016(8) 0.0006(9) C18 0.0652(13) 0.0691(14) 0.0622(13) 0.0144(10) 0.0093(10) 0.0069(10) C19 0.0789(15) 0.0565(12) 0.0578(12) -0.0006(11) 0.0166(10) -0.0014(9) C20 0.0651(12) 0.0630(13) 0.0452(10) -0.0139(10) -0.0008(9) 0.0018(9) N21 0.0834(16) 0.0845(16) 0.0854(15) -0.0264(13) -0.0166(12) 0.0011(12) O22 0.0803(14) 0.1120(17) 0.145(2) -0.0256(12) -0.0423(13) 0.0251(14) O23 0.139(2) 0.0982(18) 0.193(3) -0.0374(15) -0.0220(19) -0.0522(18) C24 0.0511(11) 0.0657(13) 0.0512(11) -0.0017(9) -0.0047(8) 0.0100(9) C25 0.0425(9) 0.0546(10) 0.0468(10) -0.0028(8) -0.0010(7) 0.0027(8) O26 0.0492(8) 0.1128(13) 0.0504(8) -0.0042(8) -0.0107(6) 0.0035(8) C27 0.0438(9) 0.0478(10) 0.0465(10) 0.0035(7) 0.0033(7) 0.0048(7) C28 0.0459(10) 0.0640(12) 0.0650(12) 0.0042(9) 0.0076(9) 0.0114(10) C29 0.0605(13) 0.0664(13) 0.0685(13) 0.0044(10) 0.0236(10) 0.0080(10) C30 0.0847(15) 0.0540(11) 0.0485(11) 0.0050(10) 0.0223(10) 0.0049(9) C31 0.0650(12) 0.0490(10) 0.0420(9) 0.0045(8) 0.0026(8) 0.0020(8) C32 0.0481(9) 0.0413(9) 0.0430(9) 0.0043(7) 0.0039(7) 0.0018(7) C33 0.0430(9) 0.0394(8) 0.0405(8) 0.0022(7) -0.0017(7) -0.0019(7) O34 0.0449(7) 0.0613(8) 0.0513(7) -0.0023(6) -0.0056(5) -0.0105(6) 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 C2 N1 C10 112.19(15) yes C2 N1 H1 123.9 ? C10 N1 H1 123.9 ? O3 C2 N1 126.58(17) yes O3 C2 C4 126.19(18) yes N1 C2 C4 107.21(16) yes N14 C4 C5 114.48(15) yes N14 C4 C2 115.57(15) yes C5 C4 C2 101.12(14) ? N14 C4 C11 100.67(13) yes C5 C4 C11 116.09(14) ? C2 C4 C11 109.50(15) ? C6 C5 C10 119.36(18) ? C6 C5 C4 131.39(15) ? C10 C5 C4 109.24(15) ? C5 C6 C7 119.17(17) ? C5 C6 H6 120.4 ? C7 C6 H6 120.4 ? C8 C7 C6 120.5(2) ? C8 C7 H7 119.8 ? C6 C7 H7 119.8 ? C9 C8 C7 121.4(2) ? C9 C8 H8 119.3 ? C7 C8 H8 119.3 ? C10 C9 C8 117.55(18) ? C10 C9 H9 121.2 ? C8 C9 H9 121.2 ? C9 C10 C5 122.03(18) ? C9 C10 N1 128.50(17) ? C5 C10 N1 109.41(17) yes C33 C11 C25 102.15(13) ? C33 C11 C12 116.40(14) ? C25 C11 C12 114.49(15) ? C33 C11 C4 108.53(13) ? C25 C11 C4 113.69(14) ? C12 C11 C4 101.90(14) ? C16 C12 C13 117.70(16) ? C16 C12 C11 114.71(14) ? C13 C12 C11 104.40(16) ? C16 C12 H12 106.4 ? C13 C12 H12 106.4 ? C11 C12 H12 106.4 ? N14 C13 C12 106.28(15) yes N14 C13 H13A 110.5 ? C12 C13 H13A 110.5 ? N14 C13 H13B 110.5 ? C12 C13 H13B 110.5 ? H13A C13 H13B 108.7 ? C4 N14 C15 116.02(16) yes C4 N14 C13 109.10(16) yes C15 N14 C13 114.71(17) yes N14 C15 H15A 109.5 ? N14 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? N14 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? C24 C16 C17 117.19(19) ? C24 C16 C12 123.33(17) ? C17 C16 C12 119.48(16) ? C18 C17 C16 122.23(19) ? C18 C17 H17 118.9 ? C16 C17 H17 118.9 ? C19 C18 C17 120.2(2) ? C19 C18 H18 119.9 ? C17 C18 H18 119.9 ? C18 C19 C20 117.5(2) ? C18 C19 H19 121.2 ? C20 C19 H19 121.2 ? C19 C20 C24 123.37(19) yes C19 C20 N21 118.3(2) yes C24 C20 N21 118.3(2) yes O23 N21 O22 123.4(2) yes O23 N21 C20 118.1(3) yes O22 N21 C20 118.4(2) yes C20 C24 C16 119.52(19) ? C20 C24 H24 120.2 ? C16 C24 H24 120.2 ? O26 C25 C27 126.87(17) yes O26 C25 C11 125.03(17) yes C27 C25 C11 108.06(14) ? C32 C27 C28 121.68(17) ? C32 C27 C25 109.87(15) ? C28 C27 C25 128.42(17) ? C29 C28 C27 116.99(19) ? C29 C28 H28 121.5 ? C27 C28 H28 121.5 ? C28 C29 C30 121.43(19) ? C28 C29 H29 119.3 ? C30 C29 H29 119.3 ? C29 C30 C31 121.89(18) ? C29 C30 H30 119.1 ? C31 C30 H30 119.1 ? C30 C31 C32 117.21(18) ? C30 C31 H31 121.4 ? C32 C31 H31 121.4 ? C27 C32 C31 120.76(17) ? C27 C32 C33 109.97(15) ? C31 C32 C33 129.18(17) ? O34 C33 C32 126.16(16) yes O34 C33 C11 126.14(16) yes C32 C33 C11 107.69(14) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.355(3) yes N1 C10 1.399(3) yes N1 H1 0.8600 ? C2 O3 1.221(2) yes C2 C4 1.573(2) ? C4 N14 1.451(2) yes C4 C5 1.504(3) ? C4 C11 1.574(3) ? C5 C6 1.379(3) ? C5 C10 1.396(2) ? C6 C7 1.384(3) ? C6 H6 0.9300 ? C7 C8 1.382(3) ? C7 H7 0.9300 ? C8 C9 1.381(3) ? C8 H8 0.9300 ? C9 C10 1.378(3) ? C9 H9 0.9300 ? C11 C33 1.536(2) ? C11 C25 1.542(2) ? C11 C12 1.548(2) ? C12 C16 1.516(3) ? C12 C13 1.531(3) ? C12 H12 0.9800 ? C13 N14 1.456(3) yes C13 H13A 0.9700 ? C13 H13B 0.9700 ? N14 C15 1.454(3) yes C15 H15A 0.9600 ? C15 H15B 0.9600 ? C15 H15C 0.9600 ? C16 C24 1.384(3) ? C16 C17 1.396(3) ? C17 C18 1.382(3) ? C17 H17 0.9300 ? C18 C19 1.372(3) ? C18 H18 0.9300 ? C19 C20 1.372(3) ? C19 H19 0.9300 ? C20 C24 1.378(3) ? C20 N21 1.471(3) yes N21 O23 1.220(3) yes N21 O22 1.226(3) yes C24 H24 0.9300 ? C25 O26 1.206(2) yes C25 C27 1.475(3) ? C27 C32 1.387(2) ? C27 C28 1.393(3) ? C28 C29 1.376(3) ? C28 H28 0.9300 ? C29 C30 1.381(3) ? C29 H29 0.9300 ? C30 C31 1.382(3) ? C30 H30 0.9300 ? C31 C32 1.388(2) ? C31 H31 0.9300 ? C32 C33 1.480(2) ? C33 O34 1.206(2) yes 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 _geom_hbond_publ_flag N1 H1 O3 2_555 0.86 2.12 2.949(2) 162 yes C28 H28 O34 1_455 0.93 2.54 3.150(2) 124 yes C31 H31 O22 2_666 0.93 2.60 3.296(3) 133 yes C19 H19 O23 . 0.93 2.42 2.703(4) 98 yes C24 H24 O22 . 0.93 2.43 2.717(3) 98 yes 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 C10 N1 C2 O3 171.0(2) C10 N1 C2 C4 -7.5(2) O3 C2 C4 N14 -45.3(3) N1 C2 C4 N14 133.19(18) O3 C2 C4 C5 -169.5(2) N1 C2 C4 C5 9.0(2) O3 C2 C4 C11 67.4(3) N1 C2 C4 C11 -114.04(18) N14 C4 C5 C6 46.0(3) C2 C4 C5 C6 170.9(2) C11 C4 C5 C6 -70.7(2) N14 C4 C5 C10 -132.51(16) C2 C4 C5 C10 -7.57(19) C11 C4 C5 C10 110.79(17) C10 C5 C6 C7 -2.1(3) C4 C5 C6 C7 179.57(19) C5 C6 C7 C8 0.3(3) C6 C7 C8 C9 1.3(3) C7 C8 C9 C10 -1.0(3) C8 C9 C10 C5 -0.9(3) C8 C9 C10 N1 175.9(2) C6 C5 C10 C9 2.4(3) C4 C5 C10 C9 -178.85(18) C6 C5 C10 N1 -174.91(17) C4 C5 C10 N1 3.8(2) C2 N1 C10 C9 -174.5(2) C2 N1 C10 C5 2.6(2) N14 C4 C11 C33 -82.95(15) C5 C4 C11 C33 41.22(19) C2 C4 C11 C33 154.87(14) N14 C4 C11 C25 164.13(14) C5 C4 C11 C25 -71.70(18) C2 C4 C11 C25 41.95(19) N14 C4 C11 C12 40.41(15) C5 C4 C11 C12 164.58(14) C2 C4 C11 C12 -81.76(16) C33 C11 C12 C16 -40.2(2) C25 C11 C12 C16 78.79(19) C4 C11 C12 C16 -158.03(15) C33 C11 C12 C13 90.10(18) C25 C11 C12 C13 -150.94(16) C4 C11 C12 C13 -27.76(17) C16 C12 C13 N14 133.65(17) C11 C12 C13 N14 5.2(2) C5 C4 N14 C15 63.9(2) C2 C4 N14 C15 -53.0(3) C11 C4 N14 C15 -170.79(18) C5 C4 N14 C13 -164.67(15) C2 C4 N14 C13 78.4(2) C11 C4 N14 C13 -39.40(17) C12 C13 N14 C4 22.3(2) C12 C13 N14 C15 154.39(17) C13 C12 C16 C24 -25.3(3) C11 C12 C16 C24 98.2(2) C13 C12 C16 C17 154.07(18) C11 C12 C16 C17 -82.5(2) C24 C16 C17 C18 -0.3(3) C12 C16 C17 C18 -179.68(17) C16 C17 C18 C19 -0.1(3) C17 C18 C19 C20 0.6(3) C18 C19 C20 C24 -0.7(3) C18 C19 C20 N21 176.60(19) C19 C20 N21 O23 8.3(4) C24 C20 N21 O23 -174.3(3) C19 C20 N21 O22 -167.6(2) C24 C20 N21 O22 9.9(3) C19 C20 C24 C16 0.3(3) N21 C20 C24 C16 -177.01(18) C17 C16 C24 C20 0.2(3) C12 C16 C24 C20 179.58(17) C33 C11 C25 O26 164.22(19) C12 C11 C25 O26 37.5(3) C4 C11 C25 O26 -79.1(2) C33 C11 C25 C27 -13.39(18) C12 C11 C25 C27 -140.10(15) C4 C11 C25 C27 103.32(16) O26 C25 C27 C32 -170.3(2) C11 C25 C27 C32 7.3(2) O26 C25 C27 C28 7.8(3) C11 C25 C27 C28 -174.64(18) C32 C27 C28 C29 -0.4(3) C25 C27 C28 C29 -178.27(19) C27 C28 C29 C30 -1.2(3) C28 C29 C30 C31 1.9(3) C29 C30 C31 C32 -0.9(3) C28 C27 C32 C31 1.3(3) C25 C27 C32 C31 179.54(16) C28 C27 C32 C33 -175.65(16) C25 C27 C32 C33 2.6(2) C30 C31 C32 C27 -0.6(3) C30 C31 C32 C33 175.68(17) C27 C32 C33 O34 166.96(17) C31 C32 C33 O34 -9.7(3) C27 C32 C33 C11 -11.45(19) C31 C32 C33 C11 171.91(17) C25 C11 C33 O34 -163.61(17) C12 C11 C33 O34 -38.1(3) C4 C11 C33 O34 76.0(2) C25 C11 C33 C32 14.80(17) C12 C11 C33 C32 140.27(15) C4 C11 C33 C32 -105.57(15)