#------------------------------------------------------------------------------ #$Date: 2016-05-13 09:17:18 +0300 (Fri, 13 May 2016) $ #$Revision: 182931 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225233.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7225233 loop_ _publ_author_name 'Shen, Jinhai' 'Yang, Xifa' 'Wang, Fuyuan' 'Wang, Yue' 'Cheng, Guolin' 'Cui, Xiuling' _publ_section_title ; Base-Mediated Regiospecific Cascade Synthesis of N-(2-Pyridyl)pyrroles from N-Propargylic \b-Enaminones ; _journal_name_full 'RSC Adv.' _journal_paper_doi 10.1039/C6RA08987A _journal_year 2016 _chemical_formula_moiety 'C36 H28 N2 O' _chemical_formula_sum 'C36 H28 N2 O' _chemical_formula_weight 504.60 _chemical_name_systematic ; ? ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _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_date 2013-07-09 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _audit_update_record ; 2014-04-01 deposited with the CCDC. 2016-05-12 downloaded from the CCDC. ; _cell_angle_alpha 104.808(8) _cell_angle_beta 91.834(7) _cell_angle_gamma 113.724(9) _cell_formula_units_Z 2 _cell_length_a 9.4141(9) _cell_length_b 11.6808(12) _cell_length_c 14.2260(11) _cell_measurement_reflns_used 3012 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 72.4883 _cell_measurement_theta_min 3.2493 _cell_volume 1368.4(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.2312 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; 1 omega -1.00 25.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -99.0000 -60.0000 26 2 omega -47.00 23.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 45.0000 -60.0000 70 3 omega -105.00 -34.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 178.0000 -60.0000 71 4 omega -90.00 -34.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 125.0000 90.0000 56 5 omega -100.00 -13.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -77.0000 -180.0000 87 6 omega -17.00 26.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 37.0000 -120.0000 43 7 omega -90.00 15.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 111.0000 -60.0000 105 8 omega -45.00 25.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 30.0000 150.0000 70 9 omega 11.00 38.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 -19.0000 0.0000 27 10 omega 45.00 98.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -45.0000 -90.0000 53 11 omega 51.00 94.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -45.0000 -30.0000 43 12 omega 90.00 174.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 45.0000 30.0000 84 13 omega 52.00 92.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -94.0000 30.0000 40 14 omega 47.00 105.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -94.0000 90.0000 58 15 omega 48.00 74.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -61.0000 120.0000 26 16 omega 43.00 96.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -45.0000 60.0000 53 17 omega 58.00 146.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 178.0000 -90.0000 88 18 omega 49.00 88.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -30.0000 120.0000 39 19 omega 43.00 87.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -45.0000 -180.0000 44 20 omega 47.00 86.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -30.0000 0.0000 39 21 omega 39.00 85.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -30.0000 -150.0000 46 22 omega 44.00 100.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -94.0000 -60.0000 56 23 omega 41.00 105.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -94.0000 -150.0000 64 24 omega 39.00 65.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -30.0000 -120.0000 26 25 omega 66.00 171.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 15.0000 150.0000 105 26 omega 90.00 116.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -111.0000 -30.0000 26 27 omega -72.00 26.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -37.0000 -120.0000 98 28 omega -111.00 -21.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -61.0000 60.0000 90 29 omega -111.00 -21.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -61.0000 -120.0000 90 30 omega 26.00 126.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 77.0000 -30.0000 100 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0508663000 _diffrn_orient_matrix_UB_12 0.1475630000 _diffrn_orient_matrix_UB_13 0.0169375000 _diffrn_orient_matrix_UB_21 -0.1731482000 _diffrn_orient_matrix_UB_22 -0.0247149000 _diffrn_orient_matrix_UB_23 -0.0205066000 _diffrn_orient_matrix_UB_31 -0.0116689000 _diffrn_orient_matrix_UB_32 0.0182418000 _diffrn_orient_matrix_UB_33 0.1101956000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_unetI/netI 0.0380 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 9859 _diffrn_reflns_theta_full 67.07 _diffrn_reflns_theta_max 67.07 _diffrn_reflns_theta_min 3.25 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.571 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.74567 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.214 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 354 _refine_ls_number_reflns 4861 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0518 _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^)+(0.0805P)^2^+0.0614P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1379 _refine_ls_wR_factor_ref 0.1545 _reflns_number_gt 3649 _reflns_number_total 4861 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c6ra08987a2.cif _cod_data_source_block 201307114 _cod_original_cell_volume 1368.4(2) _cod_database_code 7225233 _chemical_oxdiff_formula C20H20N4O4 _reflns_odcompleteness_completeness 99.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36) 2.b Idealised Me refined as rotating group: C5(H5A,H5B,H5C), C24(H24A,H24B,H24C) ; loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags O1 O -0.02494(17) -0.34817(16) 0.43868(11) 0.0674(4) Uani 1 1 d . N1 N 0.16180(18) -0.09753(16) 0.23605(11) 0.0484(4) Uani 1 1 d . N2 N 0.33912(18) 0.05885(16) 0.17195(11) 0.0471(4) Uani 1 1 d . C1 C 0.0406(2) -0.0774(2) 0.27808(15) 0.0538(5) Uani 1 1 d . H1 H -0.0056 -0.0262 0.2626 0.065 Uiso 1 1 calc R C2 C -0.0005(2) -0.1439(2) 0.34550(14) 0.0511(5) Uani 1 1 d . C3 C 0.1016(2) -0.20695(19) 0.34687(13) 0.0466(4) Uani 1 1 d . C4 C 0.2004(2) -0.17711(18) 0.27719(13) 0.0456(4) Uani 1 1 d . C5 C -0.1273(3) -0.1468(3) 0.40828(17) 0.0691(6) Uani 1 1 d . H5A H -0.2143 -0.2316 0.3865 0.104 Uiso 1 1 calc R H5B H -0.1617 -0.0815 0.4026 0.104 Uiso 1 1 calc R H5C H -0.0865 -0.1292 0.4757 0.104 Uiso 1 1 calc R C6 C 0.0989(2) -0.28602(19) 0.41261(13) 0.0500(5) Uani 1 1 d . C7 C 0.2470(2) -0.28794(19) 0.45232(13) 0.0490(4) Uani 1 1 d . C8 C 0.2384(3) -0.4004(2) 0.47266(17) 0.0654(6) Uani 1 1 d . H8 H 0.1426 -0.4732 0.4603 0.078 Uiso 1 1 calc R C9 C 0.3727(4) -0.4037(3) 0.5113(2) 0.0791(7) Uani 1 1 d . H9 H 0.3676 -0.4801 0.5228 0.095 Uiso 1 1 calc R C10 C 0.5137(3) -0.2952(3) 0.5327(2) 0.0790(7) Uani 1 1 d . H10 H 0.6034 -0.2983 0.5589 0.095 Uiso 1 1 calc R C11 C 0.5228(3) -0.1818(3) 0.51585(18) 0.0681(6) Uani 1 1 d . H11 H 0.6177 -0.1074 0.5324 0.082 Uiso 1 1 calc R C12 C 0.3901(2) -0.1791(2) 0.47405(15) 0.0562(5) Uani 1 1 d . H12 H 0.3968 -0.1036 0.4604 0.067 Uiso 1 1 calc R C13 C 0.3192(2) -0.2245(2) 0.24336(14) 0.0502(5) Uani 1 1 d . C14 C 0.2817(3) -0.3570(2) 0.21649(17) 0.0660(6) Uani 1 1 d . H14 H 0.1799 -0.4168 0.2160 0.079 Uiso 1 1 calc R C15 C 0.3959(4) -0.4010(3) 0.1903(2) 0.0895(9) Uani 1 1 d . H15 H 0.3705 -0.4900 0.1726 0.107 Uiso 1 1 calc R C16 C 0.5459(4) -0.3135(4) 0.1904(2) 0.0932(10) Uani 1 1 d . H16 H 0.6219 -0.3435 0.1730 0.112 Uiso 1 1 calc R C17 C 0.5842(3) -0.1827(4) 0.2158(2) 0.0817(8) Uani 1 1 d . H17 H 0.6861 -0.1239 0.2152 0.098 Uiso 1 1 calc R C18 C 0.4718(2) -0.1371(3) 0.24262(16) 0.0606(6) Uani 1 1 d . H18 H 0.4986 -0.0478 0.2601 0.073 Uiso 1 1 calc R C19 C 0.2151(2) -0.05518(19) 0.15161(14) 0.0459(4) Uani 1 1 d . C20 C 0.1291(2) -0.1315(2) 0.05867(14) 0.0484(4) Uani 1 1 d . C21 C 0.1778(2) -0.07897(19) -0.01961(14) 0.0453(4) Uani 1 1 d . C22 C 0.3079(2) 0.0407(2) 0.00158(14) 0.0489(4) Uani 1 1 d . H22 H 0.3426 0.0768 -0.0492 0.059 Uiso 1 1 calc R C23 C 0.3874(2) 0.10788(19) 0.09686(14) 0.0461(4) Uani 1 1 d . C24 C -0.0032(3) -0.2638(2) 0.04534(17) 0.0702(6) Uani 1 1 d . H24A H -0.0982 -0.2542 0.0571 0.105 Uiso 1 1 calc R H24B H 0.0211 -0.3036 0.0910 0.105 Uiso 1 1 calc R H24C H -0.0170 -0.3181 -0.0206 0.105 Uiso 1 1 calc R C25 C 0.0966(2) -0.14438(19) -0.12285(14) 0.0476(4) Uani 1 1 d . C26 C -0.0653(2) -0.1935(2) -0.14722(16) 0.0586(5) Uani 1 1 d . H26 H -0.1264 -0.1882 -0.0976 0.070 Uiso 1 1 calc R C27 C -0.1363(3) -0.2498(2) -0.24388(18) 0.0692(6) Uani 1 1 d . H27 H -0.2448 -0.2826 -0.2588 0.083 Uiso 1 1 calc R C28 C -0.0484(3) -0.2582(2) -0.31859(17) 0.0691(6) Uani 1 1 d . H28 H -0.0969 -0.2965 -0.3838 0.083 Uiso 1 1 calc R C29 C 0.1122(3) -0.2092(3) -0.29589(17) 0.0744(7) Uani 1 1 d . H29 H 0.1726 -0.2144 -0.3459 0.089 Uiso 1 1 calc R C30 C 0.1835(3) -0.1525(2) -0.19907(16) 0.0610(5) Uani 1 1 d . H30 H 0.2921 -0.1189 -0.1847 0.073 Uiso 1 1 calc R C31 C 0.5243(2) 0.2381(2) 0.12195(14) 0.0489(4) Uani 1 1 d . C32 C 0.6048(3) 0.2868(2) 0.05064(17) 0.0654(6) Uani 1 1 d . H32 H 0.5729 0.2376 -0.0152 0.078 Uiso 1 1 calc R C33 C 0.7321(3) 0.4080(3) 0.07651(19) 0.0778(7) Uani 1 1 d . H33 H 0.7842 0.4400 0.0279 0.093 Uiso 1 1 calc R C34 C 0.7821(3) 0.4814(2) 0.1732(2) 0.0744(7) Uani 1 1 d . H34 H 0.8678 0.5627 0.1901 0.089 Uiso 1 1 calc R C35 C 0.7049(3) 0.4341(2) 0.24476(18) 0.0718(7) Uani 1 1 d . H35 H 0.7386 0.4832 0.3105 0.086 Uiso 1 1 calc R C36 C 0.5773(3) 0.3138(2) 0.21918(16) 0.0625(6) Uani 1 1 d . H36 H 0.5257 0.2828 0.2683 0.075 Uiso 1 1 calc R 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 0.0538(8) 0.0739(10) 0.0644(9) 0.0386(8) 0.0131(7) 0.0060(7) N1 0.0450(8) 0.0570(9) 0.0461(8) 0.0247(7) 0.0095(6) 0.0187(7) N2 0.0430(8) 0.0546(9) 0.0433(8) 0.0208(7) 0.0061(6) 0.0165(7) C1 0.0482(10) 0.0669(13) 0.0537(11) 0.0247(10) 0.0126(8) 0.0271(10) C2 0.0413(10) 0.0604(12) 0.0463(10) 0.0182(9) 0.0098(8) 0.0147(9) C3 0.0394(9) 0.0514(11) 0.0400(9) 0.0171(8) 0.0034(7) 0.0082(8) C4 0.0410(9) 0.0487(10) 0.0412(9) 0.0192(8) 0.0035(7) 0.0096(8) C5 0.0593(13) 0.0922(18) 0.0604(13) 0.0301(12) 0.0239(10) 0.0310(12) C6 0.0509(11) 0.0477(10) 0.0384(9) 0.0152(8) 0.0059(8) 0.0066(8) C7 0.0583(11) 0.0488(10) 0.0373(9) 0.0185(8) 0.0101(8) 0.0163(9) C8 0.0796(15) 0.0570(13) 0.0642(13) 0.0263(11) 0.0203(11) 0.0279(11) C9 0.103(2) 0.0820(18) 0.0826(17) 0.0452(15) 0.0287(15) 0.0554(17) C10 0.0825(17) 0.109(2) 0.0730(16) 0.0425(15) 0.0177(13) 0.0584(17) C11 0.0578(13) 0.0811(16) 0.0655(14) 0.0250(12) 0.0025(10) 0.0282(12) C12 0.0576(12) 0.0555(12) 0.0535(11) 0.0223(9) 0.0014(9) 0.0188(9) C13 0.0488(10) 0.0660(13) 0.0416(9) 0.0264(9) 0.0097(8) 0.0237(9) C14 0.0704(14) 0.0726(15) 0.0624(13) 0.0265(11) 0.0152(11) 0.0332(12) C15 0.113(2) 0.101(2) 0.0881(19) 0.0394(17) 0.0331(17) 0.070(2) C16 0.095(2) 0.147(3) 0.093(2) 0.065(2) 0.0406(17) 0.085(2) C17 0.0590(14) 0.136(3) 0.0826(17) 0.0669(18) 0.0269(12) 0.0519(16) C18 0.0492(11) 0.0866(16) 0.0572(12) 0.0399(11) 0.0127(9) 0.0283(11) C19 0.0419(9) 0.0542(11) 0.0473(10) 0.0245(8) 0.0103(7) 0.0198(8) C20 0.0439(10) 0.0521(11) 0.0479(10) 0.0195(8) 0.0074(8) 0.0161(8) C21 0.0446(9) 0.0498(10) 0.0440(9) 0.0183(8) 0.0078(7) 0.0196(8) C22 0.0476(10) 0.0547(11) 0.0446(10) 0.0229(9) 0.0103(8) 0.0167(9) C23 0.0412(9) 0.0529(11) 0.0453(10) 0.0220(8) 0.0081(7) 0.0163(8) C24 0.0691(14) 0.0632(14) 0.0594(13) 0.0280(11) 0.0041(11) 0.0039(11) C25 0.0476(10) 0.0468(10) 0.0472(10) 0.0172(8) 0.0050(8) 0.0169(8) C26 0.0509(11) 0.0674(13) 0.0537(11) 0.0182(10) 0.0050(9) 0.0213(10) C27 0.0587(13) 0.0720(15) 0.0654(14) 0.0182(12) -0.0071(10) 0.0187(11) C28 0.0867(17) 0.0633(14) 0.0476(12) 0.0069(10) -0.0084(11) 0.0294(12) C29 0.0905(18) 0.0936(19) 0.0473(12) 0.0171(12) 0.0163(11) 0.0490(16) C30 0.0570(12) 0.0779(15) 0.0506(11) 0.0206(10) 0.0113(9) 0.0301(11) C31 0.0415(9) 0.0535(11) 0.0501(10) 0.0217(9) 0.0050(8) 0.0149(8) C32 0.0606(13) 0.0653(14) 0.0543(12) 0.0237(11) 0.0054(10) 0.0077(11) C33 0.0656(14) 0.0746(16) 0.0720(15) 0.0350(13) 0.0124(12) 0.0006(12) C34 0.0559(13) 0.0609(14) 0.0828(17) 0.0249(13) 0.0003(11) -0.0001(11) C35 0.0623(14) 0.0662(15) 0.0610(14) 0.0120(11) -0.0031(11) 0.0069(11) C36 0.0557(12) 0.0668(14) 0.0500(11) 0.0179(10) 0.0063(9) 0.0110(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C1 N1 C19 121.89(15) C4 N1 C1 109.27(16) C4 N1 C19 128.14(16) C19 N2 C23 117.75(16) N1 C1 H1 125.4 C2 C1 N1 109.21(18) C2 C1 H1 125.4 C1 C2 C3 106.82(17) C1 C2 C5 125.9(2) C3 C2 C5 127.24(19) C2 C3 C6 124.07(17) C4 C3 C2 107.54(17) C4 C3 C6 128.38(18) N1 C4 C3 107.15(17) N1 C4 C13 122.66(16) C3 C4 C13 130.06(17) C2 C5 H5A 109.5 C2 C5 H5B 109.5 C2 C5 H5C 109.5 H5A C5 H5B 109.5 H5A C5 H5C 109.5 H5B C5 H5C 109.5 O1 C6 C3 120.10(19) O1 C6 C7 118.98(18) C3 C6 C7 120.87(16) C8 C7 C6 118.61(19) C12 C7 C6 122.10(18) C12 C7 C8 119.2(2) C7 C8 H8 120.1 C9 C8 C7 119.8(2) C9 C8 H8 120.1 C8 C9 H9 119.8 C10 C9 C8 120.5(2) C10 C9 H9 119.8 C9 C10 H10 119.8 C9 C10 C11 120.3(2) C11 C10 H10 119.8 C10 C11 H11 120.2 C10 C11 C12 119.5(2) C12 C11 H11 120.2 C7 C12 H12 119.7 C11 C12 C7 120.7(2) C11 C12 H12 119.7 C14 C13 C4 120.19(19) C14 C13 C18 118.9(2) C18 C13 C4 120.8(2) C13 C14 H14 119.9 C13 C14 C15 120.2(3) C15 C14 H14 119.9 C14 C15 H15 119.9 C16 C15 C14 120.2(3) C16 C15 H15 119.9 C15 C16 H16 119.8 C17 C16 C15 120.3(3) C17 C16 H16 119.8 C16 C17 H17 119.9 C16 C17 C18 120.2(3) C18 C17 H17 119.9 C13 C18 H18 119.9 C17 C18 C13 120.2(3) C17 C18 H18 119.9 N2 C19 N1 115.05(17) N2 C19 C20 126.18(17) C20 C19 N1 118.67(17) C19 C20 C21 116.03(17) C19 C20 C24 120.46(17) C21 C20 C24 123.46(18) C20 C21 C25 123.43(17) C22 C21 C20 117.86(17) C22 C21 C25 118.71(16) C21 C22 H22 119.2 C21 C22 C23 121.51(17) C23 C22 H22 119.2 N2 C23 C22 120.64(17) N2 C23 C31 116.77(17) C22 C23 C31 122.54(16) C20 C24 H24A 109.5 C20 C24 H24B 109.5 C20 C24 H24C 109.5 H24A C24 H24B 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 C26 C25 C21 122.29(18) C30 C25 C21 119.91(18) C30 C25 C26 117.73(19) C25 C26 H26 119.6 C27 C26 C25 120.8(2) C27 C26 H26 119.6 C26 C27 H27 119.7 C28 C27 C26 120.7(2) C28 C27 H27 119.7 C27 C28 H28 120.3 C27 C28 C29 119.3(2) C29 C28 H28 120.3 C28 C29 H29 120.0 C28 C29 C30 120.1(2) C30 C29 H29 120.0 C25 C30 H30 119.3 C29 C30 C25 121.4(2) C29 C30 H30 119.3 C32 C31 C23 122.08(19) C36 C31 C23 120.15(17) C36 C31 C32 117.76(19) C31 C32 H32 119.7 C33 C32 C31 120.6(2) C33 C32 H32 119.7 C32 C33 H33 119.7 C34 C33 C32 120.6(2) C34 C33 H33 119.7 C33 C34 H34 120.2 C33 C34 C35 119.6(2) C35 C34 H34 120.2 C34 C35 H35 120.0 C34 C35 C36 120.0(2) C36 C35 H35 120.0 C31 C36 H36 119.3 C35 C36 C31 121.5(2) C35 C36 H36 119.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C6 1.228(2) N1 C1 1.379(2) N1 C4 1.369(2) N1 C19 1.443(2) N2 C19 1.323(2) N2 C23 1.345(2) C1 H1 0.9300 C1 C2 1.355(3) C2 C3 1.429(3) C2 C5 1.508(3) C3 C4 1.394(3) C3 C6 1.467(3) C4 C13 1.478(3) C5 H5A 0.9600 C5 H5B 0.9600 C5 H5C 0.9600 C6 C7 1.499(3) C7 C8 1.387(3) C7 C12 1.385(3) C8 H8 0.9300 C8 C9 1.382(4) C9 H9 0.9300 C9 C10 1.372(4) C10 H10 0.9300 C10 C11 1.375(4) C11 H11 0.9300 C11 C12 1.382(3) C12 H12 0.9300 C13 C14 1.384(3) C13 C18 1.391(3) C14 H14 0.9300 C14 C15 1.389(3) C15 H15 0.9300 C15 C16 1.369(4) C16 H16 0.9300 C16 C17 1.365(5) C17 H17 0.9300 C17 C18 1.388(3) C18 H18 0.9300 C19 C20 1.395(3) C20 C21 1.408(3) C20 C24 1.504(3) C21 C22 1.389(3) C21 C25 1.487(3) C22 H22 0.9300 C22 C23 1.390(3) C23 C31 1.489(3) C24 H24A 0.9600 C24 H24B 0.9600 C24 H24C 0.9600 C25 C26 1.391(3) C25 C30 1.385(3) C26 H26 0.9300 C26 C27 1.377(3) C27 H27 0.9300 C27 C28 1.376(4) C28 H28 0.9300 C28 C29 1.376(4) C29 H29 0.9300 C29 C30 1.380(3) C30 H30 0.9300 C31 C32 1.387(3) C31 C36 1.386(3) C32 H32 0.9300 C32 C33 1.384(3) C33 H33 0.9300 C33 C34 1.370(4) C34 H34 0.9300 C34 C35 1.372(3) C35 H35 0.9300 C35 C36 1.379(3) C36 H36 0.9300 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 O1 C6 C7 C8 32.7(3) O1 C6 C7 C12 -143.8(2) N1 C1 C2 C3 1.0(2) N1 C1 C2 C5 179.5(2) N1 C4 C13 C14 -126.4(2) N1 C4 C13 C18 56.8(3) N1 C19 C20 C21 174.07(17) N1 C19 C20 C24 -8.1(3) N2 C19 C20 C21 -1.9(3) N2 C19 C20 C24 175.9(2) N2 C23 C31 C32 166.6(2) N2 C23 C31 C36 -12.1(3) C1 N1 C4 C3 -0.3(2) C1 N1 C4 C13 175.83(18) C1 N1 C19 N2 96.9(2) C1 N1 C19 C20 -79.5(2) C1 C2 C3 C4 -1.2(2) C1 C2 C3 C6 178.03(18) C2 C3 C4 N1 0.9(2) C2 C3 C4 C13 -174.85(18) C2 C3 C6 O1 31.4(3) C2 C3 C6 C7 -146.02(19) C3 C4 C13 C14 48.7(3) C3 C4 C13 C18 -128.1(2) C3 C6 C7 C8 -149.9(2) C3 C6 C7 C12 33.6(3) C4 N1 C1 C2 -0.5(2) C4 N1 C19 N2 -93.7(2) C4 N1 C19 C20 89.8(2) C4 C3 C6 O1 -149.6(2) C4 C3 C6 C7 33.0(3) C4 C13 C14 C15 -176.2(2) C4 C13 C18 C17 176.45(19) C5 C2 C3 C4 -179.7(2) C5 C2 C3 C6 -0.5(3) C6 C3 C4 N1 -178.26(18) C6 C3 C4 C13 6.0(3) C6 C7 C8 C9 -178.6(2) C6 C7 C12 C11 176.26(19) C7 C8 C9 C10 2.2(4) C8 C7 C12 C11 -0.3(3) C8 C9 C10 C11 -0.2(4) C9 C10 C11 C12 -2.1(4) C10 C11 C12 C7 2.3(4) C12 C7 C8 C9 -2.0(3) C13 C14 C15 C16 -0.3(4) C14 C13 C18 C17 -0.4(3) C14 C15 C16 C17 -0.3(5) C15 C16 C17 C18 0.5(4) C16 C17 C18 C13 -0.2(4) C18 C13 C14 C15 0.6(3) C19 N1 C1 C2 170.65(18) C19 N1 C4 C3 -170.68(18) C19 N1 C4 C13 5.4(3) C19 N2 C23 C22 0.6(3) C19 N2 C23 C31 178.26(17) C19 C20 C21 C22 1.7(3) C19 C20 C21 C25 -177.76(17) C20 C21 C22 C23 -0.6(3) C20 C21 C25 C26 48.4(3) C20 C21 C25 C30 -134.7(2) C21 C22 C23 N2 -0.6(3) C21 C22 C23 C31 -178.20(18) C21 C25 C26 C27 177.9(2) C21 C25 C30 C29 -178.2(2) C22 C21 C25 C26 -131.1(2) C22 C21 C25 C30 45.8(3) C22 C23 C31 C32 -15.7(3) C22 C23 C31 C36 165.5(2) C23 N2 C19 N1 -175.36(16) C23 N2 C19 C20 0.8(3) C23 C31 C32 C33 -179.7(2) C23 C31 C36 C35 179.2(2) C24 C20 C21 C22 -176.0(2) C24 C20 C21 C25 4.5(3) C25 C21 C22 C23 178.93(17) C25 C26 C27 C28 -0.4(4) C26 C25 C30 C29 -1.1(3) C26 C27 C28 C29 -0.1(4) C27 C28 C29 C30 0.0(4) C28 C29 C30 C25 0.6(4) C30 C25 C26 C27 1.0(3) C31 C32 C33 C34 0.8(4) C32 C31 C36 C35 0.5(4) C32 C33 C34 C35 -0.1(4) C33 C34 C35 C36 -0.4(4) C34 C35 C36 C31 0.2(4) C36 C31 C32 C33 -0.9(4)