#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206884.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_2206884 loop_ _publ_author_name 'S. Selvanayagam' 'D. Velmurugan' 'K. Ravikumar' 'B. Sridhar' 'E. Ramesh' _publ_section_title 4-[Bis(2-methyl-1H-indol-3-yl)methyl]-1-(4-methoxyphenyl)-3-phenylazetidin-2-one _journal_coeditor_code BT6740 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3386 _journal_page_last o3388 _journal_paper_doi 10.1107/S1600536805029557 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C35 H31 N3 O2' _chemical_formula_moiety 'C35 H31 N3 O2' _chemical_formula_sum 'C35 H31 N3 O2' _chemical_formula_weight 525.63 _chemical_name_systematic ; 4-[Bis(2-methyl-1H-indol-3-yl)methyl]-1-(4-methoxyphenyl)-3-phenylazetidin- 2-one ; _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 91.9780(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.9751(7) _cell_length_b 13.4815(8) _cell_length_c 17.2114(11) _cell_measurement_reflns_used 11212 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.36 _cell_measurement_theta_min 2.18 _cell_volume 2777.0(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 0.968 _diffrn_measurement_device 'Bruker SMART APEX' _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 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 31001 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.04 _diffrn_reflns_theta_min 1.92 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 1112 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.300 _refine_diff_density_min -0.224 _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 362 _refine_ls_number_reflns 6519 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0492 _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^)+(0.08P)^2^+0.5932P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1387 _refine_ls_wR_factor_ref 0.1485 _reflns_number_gt 5325 _reflns_number_total 6519 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6740.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2206884 _cod_database_fobs_code 2206884 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_type_symbol O1 0.59029(9) 0.23703(8) 0.11658(6) 0.0554(3) Uani d . 1 O O2 0.68659(10) -0.21135(9) -0.03740(7) 0.0632(3) Uani d . 1 O N1 0.54200(10) 0.07997(9) 0.16433(6) 0.0429(3) Uani d . 1 N N2 0.71139(11) -0.15471(11) 0.33046(8) 0.0584(3) Uani d . 1 N H2 0.7783 -0.1776 0.3354 0.070 Uiso calc R 1 H N3 0.36215(11) 0.11854(9) 0.48359(7) 0.0509(3) Uani d . 1 N H3 0.3620 0.1420 0.5300 0.061 Uiso calc R 1 H C1 0.45976(11) 0.07649(10) 0.22669(7) 0.0392(3) Uani d . 1 C H1 0.3931 0.0375 0.2124 0.047 Uiso calc R 1 H C2 0.44312(11) 0.19115(10) 0.21277(8) 0.0435(3) Uani d . 1 C H2A 0.3727 0.2020 0.1832 0.052 Uiso calc R 1 H C3 0.53734(11) 0.18046(10) 0.15643(7) 0.0435(3) Uani d . 1 C C4 0.58073(11) 0.00436(11) 0.11538(7) 0.0432(3) Uani d . 1 C C5 0.54765(14) -0.09251(11) 0.12555(8) 0.0528(4) Uani d . 1 C H5 0.5024 -0.1083 0.1666 0.063 Uiso calc R 1 H C6 0.58059(14) -0.16690(12) 0.07578(8) 0.0543(4) Uani d . 1 C H6 0.5572 -0.2319 0.0833 0.065 Uiso calc R 1 H C7 0.64828(12) -0.14412(12) 0.01494(8) 0.0486(3) Uani d . 1 C C8 0.68095(14) -0.04706(13) 0.00443(9) 0.0559(4) Uani d . 1 C H8 0.7261 -0.0316 -0.0368 0.067 Uiso calc R 1 H C9 0.64835(13) 0.02742(12) 0.05349(8) 0.0511(3) Uani d . 1 C H9 0.6712 0.0924 0.0454 0.061 Uiso calc R 1 H C10 0.65488(16) -0.31203(13) -0.02868(10) 0.0618(4) Uani d . 1 C H10A 0.6871 -0.3511 -0.0688 0.093 Uiso calc R 1 H H10B 0.5749 -0.3173 -0.0326 0.093 Uiso calc R 1 H H10C 0.6812 -0.3358 0.0212 0.093 Uiso calc R 1 H C11 0.50927(10) 0.05056(9) 0.30724(7) 0.0372(3) Uani d . 1 C H11 0.5671 0.1008 0.3176 0.045 Uiso calc R 1 H C12 0.56971(11) -0.04732(10) 0.31413(7) 0.0398(3) Uani d . 1 C C13 0.68380(12) -0.05656(12) 0.31915(8) 0.0498(3) Uani d . 1 C C14 0.61568(13) -0.21048(11) 0.33260(8) 0.0497(3) Uani d . 1 C C15 0.60232(17) -0.31206(13) 0.34411(10) 0.0660(5) Uani d . 1 C H15 0.6636 -0.3537 0.3520 0.079 Uiso calc R 1 H C16 0.49572(19) -0.34809(13) 0.34338(12) 0.0736(5) Uani d . 1 C H16 0.4843 -0.4157 0.3504 0.088 Uiso calc R 1 H C17 0.40370(16) -0.28600(13) 0.33237(11) 0.0655(4) Uani d . 1 C H17 0.3322 -0.3129 0.3324 0.079 Uiso calc R 1 H C18 0.41653(13) -0.18540(11) 0.32138(9) 0.0497(3) Uani d . 1 C H18 0.3544 -0.1447 0.3136 0.060 Uiso calc R 1 H C19 0.52436(11) -0.14537(10) 0.32206(7) 0.0410(3) Uani d . 1 C C20 0.77400(14) 0.01888(17) 0.31435(13) 0.0749(5) Uani d . 1 C H20A 0.8454 -0.0130 0.3208 0.112 Uiso calc R 1 H H20B 0.7659 0.0673 0.3546 0.112 Uiso calc R 1 H H20C 0.7689 0.0510 0.2646 0.112 Uiso calc R 1 H C21 0.42471(11) 0.06678(9) 0.36965(7) 0.0366(3) Uani d . 1 C C22 0.45547(12) 0.10554(10) 0.44083(8) 0.0429(3) Uani d . 1 C C23 0.26937(12) 0.08868(11) 0.44159(8) 0.0471(3) Uani d . 1 C C24 0.15778(15) 0.08975(14) 0.46154(10) 0.0624(4) Uani d . 1 C H24 0.1367 0.1130 0.5097 0.075 Uiso calc R 1 H C25 0.07993(14) 0.05536(15) 0.40781(11) 0.0672(5) Uani d . 1 C H25 0.0048 0.0549 0.4198 0.081 Uiso calc R 1 H C26 0.11188(13) 0.02097(14) 0.33533(10) 0.0590(4) Uani d . 1 C H26 0.0576 -0.0023 0.2999 0.071 Uiso calc R 1 H C27 0.22223(12) 0.02095(11) 0.31529(8) 0.0462(3) Uani d . 1 C H27 0.2418 -0.0017 0.2666 0.055 Uiso calc R 1 H C28 0.30526(11) 0.05503(9) 0.36841(7) 0.0392(3) Uani d . 1 C C29 0.56762(14) 0.13309(12) 0.47331(9) 0.0550(4) Uani d . 1 C H29A 0.5955 0.0809 0.5066 0.082 Uiso calc R 1 H H29B 0.5622 0.1933 0.5027 0.082 Uiso calc R 1 H H29C 0.6177 0.1428 0.4316 0.082 Uiso calc R 1 H C30 0.45151(15) 0.26413(10) 0.27847(9) 0.0537(4) Uani d . 1 C C31 0.3540(2) 0.29040(13) 0.31582(11) 0.0742(5) Uani d . 1 C H31 0.2854 0.2663 0.2973 0.089 Uiso calc R 1 H C32 0.3587(3) 0.35138(18) 0.37954(15) 0.1077(10) Uani d . 1 C H32 0.2936 0.3672 0.4046 0.129 Uiso calc R 1 H C33 0.4580(4) 0.38870(18) 0.40616(15) 0.1189(12) Uani d . 1 C H33 0.4604 0.4294 0.4498 0.143 Uiso calc R 1 H C34 0.5571(3) 0.36657(16) 0.36862(15) 0.1045(10) Uani d . 1 C H34 0.6248 0.3937 0.3862 0.125 Uiso calc R 1 H C35 0.5523(2) 0.30309(13) 0.30442(11) 0.0711(5) Uani d . 1 C H35 0.6173 0.2871 0.2792 0.085 Uiso calc R 1 H 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 0.0586(6) 0.0538(6) 0.0539(6) -0.0159(5) 0.0054(5) 0.0109(5) O2 0.0743(8) 0.0664(7) 0.0499(6) -0.0029(6) 0.0176(5) -0.0118(5) N1 0.0491(6) 0.0456(6) 0.0346(5) -0.0074(5) 0.0076(4) 0.0017(4) N2 0.0457(7) 0.0695(9) 0.0599(8) 0.0184(6) 0.0030(6) -0.0039(6) N3 0.0646(8) 0.0544(7) 0.0339(5) 0.0040(6) 0.0066(5) -0.0075(5) C1 0.0410(6) 0.0433(7) 0.0334(6) -0.0056(5) 0.0042(5) 0.0001(5) C2 0.0452(7) 0.0460(7) 0.0390(6) -0.0002(5) -0.0013(5) 0.0056(5) C3 0.0451(7) 0.0476(7) 0.0374(6) -0.0077(5) -0.0033(5) 0.0037(5) C4 0.0463(7) 0.0508(7) 0.0326(6) -0.0051(6) 0.0028(5) -0.0012(5) C5 0.0666(9) 0.0529(8) 0.0398(7) -0.0098(7) 0.0159(6) -0.0005(6) C6 0.0719(10) 0.0493(8) 0.0422(7) -0.0085(7) 0.0112(7) -0.0018(6) C7 0.0513(8) 0.0587(8) 0.0360(6) -0.0017(6) 0.0033(5) -0.0049(6) C8 0.0604(9) 0.0660(10) 0.0424(7) -0.0109(7) 0.0175(6) -0.0015(7) C9 0.0558(8) 0.0548(8) 0.0433(7) -0.0134(6) 0.0112(6) 0.0009(6) C10 0.0690(10) 0.0583(9) 0.0581(9) 0.0105(8) 0.0022(8) -0.0078(7) C11 0.0396(6) 0.0382(6) 0.0339(6) -0.0028(5) 0.0026(5) -0.0001(5) C12 0.0412(6) 0.0451(7) 0.0333(6) 0.0023(5) 0.0045(5) -0.0011(5) C13 0.0434(7) 0.0618(9) 0.0444(7) 0.0045(6) 0.0058(6) -0.0020(6) C14 0.0560(8) 0.0530(8) 0.0401(7) 0.0144(6) 0.0027(6) -0.0047(6) C15 0.0852(12) 0.0510(9) 0.0614(10) 0.0248(8) -0.0036(9) -0.0035(7) C16 0.1003(15) 0.0410(8) 0.0791(12) 0.0051(9) -0.0032(10) 0.0009(8) C17 0.0719(11) 0.0490(9) 0.0757(11) -0.0075(8) 0.0027(9) -0.0020(8) C18 0.0515(8) 0.0434(7) 0.0541(8) 0.0012(6) 0.0027(6) -0.0020(6) C19 0.0491(7) 0.0421(7) 0.0320(6) 0.0068(5) 0.0044(5) -0.0018(5) C20 0.0434(8) 0.0929(14) 0.0890(13) -0.0078(9) 0.0096(8) 0.0001(11) C21 0.0434(6) 0.0340(6) 0.0325(6) 0.0017(5) 0.0021(5) 0.0018(4) C22 0.0537(7) 0.0398(6) 0.0352(6) 0.0014(5) 0.0011(5) 0.0013(5) C23 0.0544(8) 0.0449(7) 0.0424(7) 0.0066(6) 0.0088(6) -0.0005(5) C24 0.0619(9) 0.0698(10) 0.0566(9) 0.0108(8) 0.0199(8) -0.0047(8) C25 0.0451(8) 0.0845(12) 0.0728(11) 0.0091(8) 0.0161(8) 0.0003(9) C26 0.0449(8) 0.0701(10) 0.0620(9) 0.0010(7) -0.0005(7) 0.0032(8) C27 0.0455(7) 0.0510(8) 0.0420(7) 0.0022(6) 0.0029(5) 0.0011(6) C28 0.0448(7) 0.0357(6) 0.0374(6) 0.0052(5) 0.0050(5) 0.0026(5) C29 0.0645(9) 0.0580(9) 0.0418(7) -0.0074(7) -0.0082(6) -0.0011(6) C30 0.0800(11) 0.0371(7) 0.0439(7) 0.0055(7) 0.0008(7) 0.0069(6) C31 0.1076(15) 0.0491(9) 0.0669(11) 0.0260(9) 0.0176(10) 0.0048(8) C32 0.185(3) 0.0570(12) 0.0825(16) 0.0354(16) 0.0302(18) -0.0079(11) C33 0.238(4) 0.0519(12) 0.0673(14) 0.0141(18) 0.010(2) -0.0150(10) C34 0.181(3) 0.0516(11) 0.0785(15) -0.0239(14) -0.0380(17) 0.0029(10) C35 0.1068(15) 0.0486(9) 0.0566(9) -0.0134(9) -0.0135(9) 0.0042(7) 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 C7 O2 C10 117.85(12) ? C3 N1 C4 132.20(10) y C3 N1 C1 94.50(10) y C4 N1 C1 130.50(10) y C14 N2 C13 109.51(12) ? C14 N2 H2 125.2 ? C13 N2 H2 125.2 ? C23 N3 C22 109.99(11) ? C23 N3 H3 125.0 ? C22 N3 H3 125.0 ? N1 C1 C11 114.66(11) ? N1 C1 C2 86.71(9) ? C11 C1 C2 113.90(10) ? N1 C1 H1 113.0 ? C11 C1 H1 113.0 ? C2 C1 H1 113.0 ? C30 C2 C3 120.76(12) ? C30 C2 C1 121.61(11) ? C3 C2 C1 84.91(10) ? C30 C2 H2A 109.1 ? C3 C2 H2A 109.1 ? C1 C2 H2A 109.1 ? O1 C3 N1 131.17(14) ? O1 C3 C2 135.41(14) ? N1 C3 C2 93.41(10) ? C5 C4 C9 119.03(13) ? C5 C4 N1 120.46(12) ? C9 C4 N1 120.42(13) ? C4 C5 C6 121.23(13) ? C4 C5 H5 119.4 ? C6 C5 H5 119.4 ? C7 C6 C5 119.68(14) ? C7 C6 H6 120.2 ? C5 C6 H6 120.2 ? O2 C7 C8 116.00(10) y O2 C7 C6 124.80(10) y C8 C7 C6 119.14(13) ? C9 C8 C7 121.57(13) ? C9 C8 H8 119.2 ? C7 C8 H8 119.2 ? C8 C9 C4 119.34(14) ? C8 C9 H9 120.3 ? C4 C9 H9 120.3 ? O2 C10 H10A 109.5 ? O2 C10 H10B 109.5 ? H10A C10 H10B 109.5 ? O2 C10 H10C 109.5 ? H10A C10 H10C 109.5 ? H10B C10 H10C 109.5 ? C12 C11 C21 113.60(10) ? C12 C11 C1 116.20(10) y C21 C11 C1 111.20(10) y C12 C11 H11 104.8 ? C21 C11 H11 104.8 ? C1 C11 H11 104.8 ? C13 C12 C19 106.82(12) ? C13 C12 C11 123.97(12) ? C19 C12 C11 129.09(11) ? C12 C13 N2 109.27(13) ? C12 C13 C20 131.14(15) ? N2 C13 C20 119.60(14) ? N2 C14 C15 129.96(15) ? N2 C14 C19 107.48(13) ? C15 C14 C19 122.55(15) ? C16 C15 C14 117.39(16) ? C16 C15 H15 121.3 ? C14 C15 H15 121.3 ? C15 C16 C17 121.53(16) ? C15 C16 H16 119.2 ? C17 C16 H16 119.2 ? C18 C17 C16 121.26(17) ? C18 C17 H17 119.4 ? C16 C17 H17 119.4 ? C17 C18 C19 119.04(14) ? C17 C18 H18 120.5 ? C19 C18 H18 120.5 ? C18 C19 C14 118.21(13) ? C18 C19 C12 134.87(12) ? C14 C19 C12 106.92(12) ? C13 C20 H20A 109.5 ? C13 C20 H20B 109.5 ? H20A C20 H20B 109.5 ? C13 C20 H20C 109.5 ? H20A C20 H20C 109.5 ? H20B C20 H20C 109.5 ? C22 C21 C28 106.96(11) ? C22 C21 C11 121.50(12) ? C28 C21 C11 131.39(11) ? N3 C22 C21 109.26(12) ? N3 C22 C29 120.66(13) ? C21 C22 C29 130.09(13) ? N3 C23 C24 129.60(14) ? N3 C23 C28 107.36(12) ? C24 C23 C28 123.03(15) ? C25 C24 C23 117.82(15) ? C25 C24 H24 121.1 ? C23 C24 H24 121.1 ? C24 C25 C26 120.92(15) ? C24 C25 H25 119.5 ? C26 C25 H25 119.5 ? C27 C26 C25 121.23(16) ? C27 C26 H26 119.4 ? C25 C26 H26 119.4 ? C26 C27 C28 120.05(14) ? C26 C27 H27 120.0 ? C28 C27 H27 120.0 ? C27 C28 C23 116.94(12) ? C27 C28 C21 136.62(12) ? C23 C28 C21 106.44(12) ? C22 C29 H29A 109.5 ? C22 C29 H29B 109.5 ? H29A C29 H29B 109.5 ? C22 C29 H29C 109.5 ? H29A C29 H29C 109.5 ? H29B C29 H29C 109.5 ? C35 C30 C31 119.41(18) ? C35 C30 C2 122.02(16) ? C31 C30 C2 118.53(16) ? C32 C31 C30 120.5(3) ? C32 C31 H31 119.7 ? C30 C31 H31 119.7 ? C33 C32 C31 120.3(3) ? C33 C32 H32 119.8 ? C31 C32 H32 119.8 ? C32 C33 C34 120.7(2) ? C32 C33 H33 119.6 ? C34 C33 H33 119.6 ? C35 C34 C33 118.8(3) ? C35 C34 H34 120.6 ? C33 C34 H34 120.6 ? C30 C35 C34 120.1(2) ? C30 C35 H35 119.9 ? C34 C35 H35 119.9 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C3 1.218(2) y O2 C7 1.3681(18) ? O2 C10 1.419(2) ? N1 C3 1.363(2) y N1 C4 1.411(2) y N1 C1 1.482(2) y N2 C14 1.372(2) y N2 C13 1.376(2) y N2 H2 0.8600 ? N3 C23 1.365(2) y N3 C22 1.371(2) y N3 H3 0.8600 ? C1 C11 1.5293(17) ? C1 C2 1.5758(18) ? C1 H1 0.9800 ? C2 C30 1.500(2) ? C2 C3 1.5197(19) ? C2 H2A 0.9800 ? C4 C5 1.378(2) ? C4 C9 1.3951(18) ? C5 C6 1.385(2) ? C5 H5 0.9300 ? C6 C7 1.381(2) ? C6 H6 0.9300 ? C7 C8 1.379(2) ? C8 C9 1.377(2) ? C8 H8 0.9300 ? C9 H9 0.9300 ? C10 H10A 0.9600 ? C10 H10B 0.9600 ? C10 H10C 0.9600 ? C11 C12 1.5078(18) ? C11 C21 1.5172(17) ? C11 H11 0.9800 ? C12 C13 1.372(2) ? C12 C19 1.4373(19) ? C13 C20 1.488(2) ? C14 C15 1.394(2) ? C14 C19 1.4091(19) ? C15 C16 1.366(3) ? C15 H15 0.9300 ? C16 C17 1.391(3) ? C16 H16 0.9300 ? C17 C18 1.379(2) ? C17 H17 0.9300 ? C18 C19 1.399(2) ? C18 H18 0.9300 ? C20 H20A 0.9600 ? C20 H20B 0.9600 ? C20 H20C 0.9600 ? C21 C22 1.3706(18) ? C21 C28 1.4387(18) ? C22 C29 1.484(2) ? C23 C24 1.391(2) ? C23 C28 1.4192(18) ? C24 C25 1.371(3) ? C24 H24 0.9300 ? C25 C26 1.397(3) ? C25 H25 0.9300 ? C26 C27 1.377(2) ? C26 H26 0.9300 ? C27 C28 1.404(2) ? C27 H27 0.9300 ? C29 H29A 0.9600 ? C29 H29B 0.9600 ? C29 H29C 0.9600 ? C30 C35 1.376(3) ? C30 C31 1.398(3) ? C31 C32 1.370(3) ? C31 H31 0.9300 ? C32 C33 1.356(5) ? C32 H32 0.9300 ? C33 C34 1.403(5) ? C33 H33 0.9300 ? C34 C35 1.397(3) ? C34 H34 0.9300 ? C35 H35 0.9300 ? 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 N2 H2 O1 2_645 0.86 2.10 2.907(2) 157 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 C3 N1 C1 C11 -109.24(12) ? C4 N1 C1 C11 88.33(16) ? C3 N1 C1 C2 5.60(10) ? C4 N1 C1 C2 -156.83(14) ? N1 C1 C2 C30 -128.26(14) ? C11 C1 C2 C30 -12.69(18) ? N1 C1 C2 C3 -5.02(9) ? C11 C1 C2 C3 110.54(11) ? C4 N1 C3 O1 -22.7(3) ? C1 N1 C3 O1 175.37(15) ? C4 N1 C3 C2 156.14(14) ? C1 N1 C3 C2 -5.81(10) ? C30 C2 C3 O1 -51.8(2) ? C1 C2 C3 O1 -175.80(16) ? C30 C2 C3 N1 129.47(13) ? C1 C2 C3 N1 5.47(10) ? C3 N1 C4 C5 -161.00(15) ? C1 N1 C4 C5 -5.0(2) ? C3 N1 C4 C9 15.6(2) ? C1 N1 C4 C9 171.65(13) ? C9 C4 C5 C6 0.2(2) ? N1 C4 C5 C6 176.91(14) ? C4 C5 C6 C7 0.3(3) ? C10 O2 C7 C8 -180.0(2) y C10 O2 C7 C6 -0.1(2) y C5 C6 C7 O2 179.51(15) ? C5 C6 C7 C8 -0.7(2) ? O2 C7 C8 C9 -179.67(15) ? C6 C7 C8 C9 0.5(2) ? C7 C8 C9 C4 0.0(3) ? C5 C4 C9 C8 -0.4(2) ? N1 C4 C9 C8 -177.09(14) ? N1 C1 C11 C12 -58.29(15) ? C2 C1 C11 C12 -156.00(10) y N1 C1 C11 C21 169.66(10) ? C2 C1 C11 C21 72.00(10) y C21 C11 C12 C13 -124.66(14) ? C1 C11 C12 C13 104.42(15) ? C21 C11 C12 C19 50.66(17) ? C1 C11 C12 C19 -80.25(16) ? C19 C12 C13 N2 -0.55(15) ? C11 C12 C13 N2 175.66(12) ? C19 C12 C13 C20 179.39(17) ? C11 C12 C13 C20 -4.4(3) ? C14 N2 C13 C12 0.24(17) ? C14 N2 C13 C20 -179.71(15) ? C13 N2 C14 C15 -178.70(16) ? C13 N2 C14 C19 0.18(16) ? N2 C14 C15 C16 -179.99(17) ? C19 C14 C15 C16 1.3(2) ? C14 C15 C16 C17 -0.6(3) ? C15 C16 C17 C18 0.3(3) ? C16 C17 C18 C19 -0.6(3) ? C17 C18 C19 C14 1.2(2) ? C17 C18 C19 C12 -178.88(15) ? N2 C14 C19 C18 179.47(12) ? C15 C14 C19 C18 -1.6(2) ? N2 C14 C19 C12 -0.51(15) ? C15 C14 C19 C12 178.48(14) ? C13 C12 C19 C18 -179.32(15) ? C11 C12 C19 C18 4.7(2) ? C13 C12 C19 C14 0.65(14) ? C11 C12 C19 C14 -175.30(12) ? C12 C11 C21 C22 85.63(15) ? C1 C11 C21 C22 -141.03(12) ? C12 C11 C21 C28 -99.56(15) ? C1 C11 C21 C28 33.78(18) ? C23 N3 C22 C21 0.07(16) ? C23 N3 C22 C29 179.60(13) ? C28 C21 C22 N3 -0.07(15) ? C11 C21 C22 N3 175.86(11) ? C28 C21 C22 C29 -179.54(14) ? C11 C21 C22 C29 -3.6(2) ? C22 N3 C23 C24 -179.13(16) ? C22 N3 C23 C28 -0.04(16) ? N3 C23 C24 C25 179.78(17) ? C28 C23 C24 C25 0.8(3) ? C23 C24 C25 C26 -0.4(3) ? C24 C25 C26 C27 -0.4(3) ? C25 C26 C27 C28 0.6(2) ? C26 C27 C28 C23 -0.2(2) ? C26 C27 C28 C21 -179.77(15) ? N3 C23 C28 C27 -179.72(12) ? C24 C23 C28 C27 -0.6(2) ? N3 C23 C28 C21 0.00(15) ? C24 C23 C28 C21 179.16(14) ? C22 C21 C28 C27 179.68(15) ? C11 C21 C28 C27 4.3(2) ? C22 C21 C28 C23 0.04(14) ? C11 C21 C28 C23 -175.32(12) ? C3 C2 C30 C35 -18.8(2) ? C1 C2 C30 C35 85.41(18) ? C3 C2 C30 C31 163.41(13) ? C1 C2 C30 C31 -92.41(17) ? C35 C30 C31 C32 -2.5(3) ? C2 C30 C31 C32 175.42(17) ? C30 C31 C32 C33 1.4(3) ? C31 C32 C33 C34 0.7(4) ? C32 C33 C34 C35 -1.7(4) ? C31 C30 C35 C34 1.4(2) ? C2 C30 C35 C34 -176.39(16) ? C33 C34 C35 C30 0.6(3) ?