# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Toshio Kawato' 'Kiichi Amimoto' 'Masatsugu Taneda' 'Hiroyuki Koyama' _publ_contact_author_name 'Prof Toshio Kawato' _publ_contact_author_address ; Department of Chemistry Faculty of Sciences, Kyushu University 4-2-1 Ropponmatsu, Chuo-ku Fukuoka 810-8560 JAPAN ; _publ_contact_author_email KAWATO@CHEM.RC.KYUSHU-U.AC.JP _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Photochromism of polymorphic 4,4'-methylenebis(N-salicylidene-2,6-diisopropylaniline) crystals ; data_3 _database_code_CSD 220378 _audit_creation_date 2003-05-02T16:39:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 4,4'-methylenebis(N-salicylidene-2,6-diimethylaniline) ; _chemical_formula_moiety 'C31 H30 N2 O2' _chemical_formula_sum 'C31 H30 N2 O2' _chemical_formula_weight 925.14 _chemical_compound_source 'synthesis as described' _chemical_melting_point 403 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.658(2) _cell_length_b 12.96(1) _cell_length_c 9.947(2) _cell_angle_alpha 97.21(1) _cell_angle_beta 109.24(1) _cell_angle_gamma 67.062(9) _cell_volume 1290.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.8 _cell_measurement_theta_max 15.0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.5155 _diffrn_reflns_av_unetI/netI 0.0509 _diffrn_reflns_number 5343 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 27.51 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.853 _diffrn_measured_fraction_theta_max 0.853 _reflns_number_total 5067 _reflns_number_gt 2214 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Rigaku AFC7R' _computing_cell_refinement 'Rigaku AFC7R' _computing_data_reduction 'CrystalStructure v3.00' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CrystalStructure v3.00' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1443P)^2^+0.1869P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.050(11) _refine_ls_number_reflns 5067 _refine_ls_number_parameters 435 _refine_ls_number_restraints 108 _refine_ls_R_factor_all 0.1687 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.2723 _refine_ls_wR_factor_gt 0.191 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.119 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.174 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8561(4) 1.0831(5) -0.0355(3) 0.1037(15) Uani 1 1 d . . . H1 H 0.882 1.0321 0.0291 0.156 Uiso 1 1 calc R . . N1 N 0.8287(3) 0.9430(3) 0.1743(2) 0.0539(8) Uani 1 1 d . . . C1 C 0.6301(4) 1.0814(4) 0.0528(3) 0.0555(8) Uani 1 1 d . . . C2 C 0.7140(5) 1.1272(5) -0.0399(3) 0.0705(12) Uani 1 1 d . . . C3 C 0.6501(7) 1.2221(6) -0.1415(4) 0.0985(18) Uani 1 1 d . . . C4 C 0.5051(8) 1.2711(6) -0.1512(5) 0.0999(19) Uani 1 1 d . . . H4 H 0.463(3) 1.335(5) -0.220(5) 0.12 Uiso 1 1 calc R . . C5 C 0.4211(7) 1.2270(7) -0.0606(6) 0.105(2) Uani 1 1 d . . . C6 C 0.4843(5) 1.1320(6) 0.0399(4) 0.0832(14) Uani 1 1 d . . . H6 H 0.426(3) 1.1006(19) 0.102(4) 0.1 Uiso 1 1 calc R . . C7 C 0.6952(4) 0.9852(4) 0.1601(3) 0.0539(8) Uani 1 1 d . . . C8 C 0.8950(4) 0.8517(3) 0.2801(2) 0.0488(8) Uani 1 1 d . . . C9 C 0.9787(4) 0.7291(3) 0.2840(3) 0.0536(8) Uani 1 1 d . . . C10 C 0.9882(6) 0.6876(4) 0.1852(3) 0.0764(13) Uani 1 1 d . . . H10A H 1.0515 0.6 0.2039 0.115 Uiso 0.5 1 calc PR . . H10B H 1.0238 0.7457 0.1202 0.115 Uiso 0.5 1 calc PR . . H10C H 0.8953 0.6908 0.1685 0.115 Uiso 0.5 1 calc PR . . H10D H 0.9289 0.7577 0.1245 0.115 Uiso 0.5 1 calc PR . . H10E H 0.9566 0.6119 0.2082 0.115 Uiso 0.5 1 calc PR . . H10F H 1.0851 0.6668 0.1599 0.115 Uiso 0.5 1 calc PR . . C11 C 1.0533(5) 0.6419(4) 0.3843(3) 0.0604(10) Uani 1 1 d . . . C12 C 1.0469(4) 0.6762(4) 0.4775(3) 0.0566(9) Uani 1 1 d . . . C13 C 0.9632(5) 0.7994(4) 0.4703(3) 0.0611(10) Uani 1 1 d . . . C14 C 0.8859(4) 0.8903(4) 0.3726(3) 0.0551(8) Uani 1 1 d . . . C15 C 0.8003(6) 1.0242(5) 0.3672(4) 0.0813(12) Uani 1 1 d . . . H15A H 0.7541 1.0734 0.2946 0.122 Uiso 0.5 1 calc PR . . H15B H 0.8619 1.0675 0.3774 0.122 Uiso 0.5 1 calc PR . . H15C H 0.7299 1.0181 0.426 0.122 Uiso 0.5 1 calc PR . . H15D H 0.8098 1.0326 0.4374 0.122 Uiso 0.5 1 calc PR . . H15E H 0.702 1.0385 0.3546 0.122 Uiso 0.5 1 calc PR . . H15F H 0.8341 1.0879 0.306 0.122 Uiso 0.5 1 calc PR . . C16 C 1.1253(6) 0.5807(5) 0.5866(4) 0.0728(13) Uani 1 1 d . . . C17 C 1.2492(4) 0.6134(3) 0.6141(3) 0.0580(9) Uani 1 1 d . . . C18 C 1.3503(5) 0.6513(5) 0.5335(3) 0.0693(11) Uani 1 1 d . . . C19 C 1.4622(5) 0.6812(4) 0.5596(3) 0.0671(10) Uani 1 1 d . . . C20 C 1.5688(7) 0.7245(8) 0.4690(5) 0.110(2) Uani 1 1 d . . . H20A H 1.5442 0.7251 0.3985 0.166 Uiso 0.5 1 calc PR . . H20B H 1.6626 0.6648 0.4918 0.166 Uiso 0.5 1 calc PR . . H20C H 1.5669 0.8109 0.4594 0.166 Uiso 0.5 1 calc PR . . H20D H 1.6383 0.7421 0.5013 0.166 Uiso 0.5 1 calc PR . . H20E H 1.5199 0.8024 0.408 0.166 Uiso 0.5 1 calc PR . . H20F H 1.6156 0.6563 0.4404 0.166 Uiso 0.5 1 calc PR . . C21 C 1.4734(5) 0.6719(4) 0.6700(3) 0.0628(10) Uani 1 1 d . A . C22 C 1.3759(5) 0.6319(4) 0.7528(3) 0.0653(11) Uani 1 1 d . . . C23 C 1.3816(8) 0.6236(7) 0.8724(4) 0.110(2) Uani 1 1 d . . . H23A H 1.3052 0.5937 0.9154 0.164 Uiso 0.5 1 calc PR . . H23B H 1.372 0.7085 0.8717 0.164 Uiso 0.5 1 calc PR . . H23C H 1.471 0.5633 0.9064 0.164 Uiso 0.5 1 calc PR . . H23D H 1.4603 0.65 0.8803 0.164 Uiso 0.5 1 calc PR . . H23E H 1.3935 0.5352 0.9239 0.164 Uiso 0.5 1 calc PR . . H23F H 1.2945 0.6804 0.8893 0.164 Uiso 0.5 1 calc PR . . C24 C 1.2645(5) 0.6053(4) 0.7214(3) 0.0620(10) Uani 1 1 d . . . N2 N 1.5857(5) 0.7049(5) 0.6999(4) 0.0896(15) Uani 1 1 d D . . O2A O 1.8072(11) 0.6064(11) 0.8503(9) 0.113(4) Uani 0.502(9) 1 d PD A 1 H2OA H 1.7276 0.6084 0.8374 0.8(6) Uiso 0.502(9) 1 calc PRD A 1 C25A C 1.6156(11) 0.7958(10) 0.6733(7) 0.067(2) Uani 0.502(9) 1 d PD A 1 H25A H 1.5625 0.8666 0.6137 0.050(18) Uiso 0.502(9) 1 calc PR A 1 C26A C 1.7229(15) 0.819(2) 0.7173(16) 0.083(4) Uani 0.502(9) 1 d PDU A 1 C27A C 1.8161(15) 0.7300(17) 0.8092(14) 0.089(4) Uani 0.502(9) 1 d PDU A 1 C28A C 1.9053(15) 0.7629(19) 0.8546(16) 0.103(4) Uani 0.502(9) 1 d PDU A 1 H28A H 1.9643 0.7012 0.9152 0.123 Uiso 0.502(9) 1 calc PR A 1 C29A C 1.907(2) 0.895(2) 0.8074(18) 0.108(4) Uani 0.502(9) 1 d PDU A 1 H29A H 1.971 0.9189 0.8353 0.09(3) Uiso 0.502(9) 1 calc PR A 1 C30A C 1.8162(18) 0.9861(18) 0.7212(13) 0.110(4) Uani 0.502(9) 1 d PDU A 1 H30A H 1.8147 1.0731 0.6934 0.132 Uiso 0.502(9) 1 calc PR A 1 C31A C 1.7317(15) 0.9509(15) 0.6783(10) 0.091(3) Uani 0.502(9) 1 d PDU A 1 H31A H 1.6729 1.0149 0.6184 0.109 Uiso 0.502(9) 1 calc PR A 1 O2B O 1.6651(18) 0.9202(13) 0.6575(11) 0.130(5) Uani 0.498(9) 1 d PD A 2 H2OB H 1.6509 0.8822 0.6199 0.19(10) Uiso 0.498(9) 1 calc PRD A 2 C25B C 1.6642(9) 0.6588(10) 0.7661(8) 0.068(3) Uani 0.498(9) 1 d PD A 2 H25B H 1.6688 0.5732 0.8124 0.14(5) Uiso 0.498(9) 1 calc PR A 2 C26B C 1.7657(13) 0.7090(15) 0.7956(11) 0.074(3) Uani 0.498(9) 1 d PDU A 2 C27B C 1.7558(19) 0.8379(19) 0.7380(15) 0.085(4) Uani 0.498(9) 1 d PDU A 2 C28B C 1.8589(19) 0.881(2) 0.7749(15) 0.113(4) Uani 0.498(9) 1 d PDU A 2 H28B H 1.8619 0.967 0.7407 0.136 Uiso 0.498(9) 1 calc PR A 2 C29B C 1.953(2) 0.787(3) 0.8643(16) 0.112(5) Uani 0.498(9) 1 d PDU A 2 H29B H 2.0187 0.8143 0.887 0.07(2) Uiso 0.498(9) 1 calc PR A 2 C30B C 1.9548(16) 0.668(2) 0.9165(13) 0.104(4) Uani 0.498(9) 1 d PDU A 2 H30B H 2.0172 0.614 0.9769 0.125 Uiso 0.498(9) 1 calc PR A 2 C31B C 1.8664(13) 0.6209(17) 0.8841(11) 0.089(3) Uani 0.498(9) 1 d PDU A 2 H31B H 1.8711 0.5332 0.9188 0.106 Uiso 0.498(9) 1 calc PR A 2 H3 H 0.710(8) 1.262(7) -0.216(6) 0.13(2) Uiso 1 1 d . . . H5 H 0.317(11) 1.268(9) -0.062(6) 0.16(3) Uiso 1 1 d . . . H7 H 0.624(5) 0.967(4) 0.219(3) 0.063(10) Uiso 1 1 d . . . H11 H 1.123(7) 0.556(6) 0.381(4) 0.094(14) Uiso 1 1 d . . . H13 H 0.973(6) 0.823(5) 0.528(4) 0.078(12) Uiso 1 1 d . . . H16A H 1.172(8) 0.503(7) 0.573(5) 0.107(19) Uiso 1 1 d . . . H16B H 1.055(9) 0.564(7) 0.650(6) 0.14(2) Uiso 1 1 d . . . H18 H 1.340(6) 0.655(5) 0.462(4) 0.089(14) Uiso 1 1 d . . . H24 H 1.187(5) 0.574(4) 0.784(4) 0.071(11) Uiso 1 1 d . . . 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 0.0603(19) 0.135(3) 0.0582(17) 0.0214(19) 0.0004(15) -0.027(2) N1 0.0479(16) 0.0599(17) 0.0430(14) -0.0057(12) -0.0019(12) -0.0184(15) C1 0.0499(19) 0.0613(19) 0.0519(17) -0.0221(15) -0.0077(15) -0.0086(16) C2 0.063(2) 0.074(3) 0.055(2) -0.0051(19) -0.0131(19) -0.016(2) C3 0.104(4) 0.092(4) 0.061(3) 0.004(3) -0.025(3) -0.011(4) C4 0.107(4) 0.083(3) 0.080(3) -0.030(3) -0.045(4) 0.024(3) C5 0.066(3) 0.127(5) 0.113(5) -0.070(4) -0.043(3) 0.031(3) C6 0.050(2) 0.123(4) 0.076(3) -0.051(3) -0.006(2) -0.005(3) C7 0.0446(18) 0.068(2) 0.0445(16) -0.0175(16) 0.0034(14) -0.0171(17) C8 0.0441(17) 0.0516(17) 0.0429(15) -0.0049(13) -0.0019(13) -0.0194(15) C9 0.058(2) 0.0530(18) 0.0477(16) -0.0102(14) -0.0029(15) -0.0232(17) C10 0.104(4) 0.062(2) 0.060(2) -0.0210(18) -0.012(2) -0.019(3) C11 0.066(2) 0.0472(18) 0.062(2) -0.0103(16) -0.0136(18) -0.0178(18) C12 0.056(2) 0.0550(18) 0.0530(17) -0.0053(15) -0.0153(16) -0.0223(17) C13 0.065(2) 0.069(2) 0.0471(17) -0.0166(17) -0.0060(17) -0.022(2) C14 0.0494(18) 0.0574(19) 0.0504(17) -0.0140(15) 0.0022(14) -0.0142(17) C15 0.084(3) 0.075(3) 0.065(2) -0.029(2) 0.000(2) 0.004(2) C16 0.085(3) 0.065(2) 0.061(2) 0.0021(19) -0.030(2) -0.033(3) C17 0.062(2) 0.0486(17) 0.0542(18) -0.0076(15) -0.0197(17) -0.0126(17) C18 0.072(3) 0.081(3) 0.055(2) -0.0213(19) -0.0136(19) -0.022(2) C19 0.064(2) 0.072(2) 0.064(2) -0.0246(19) -0.0068(19) -0.017(2) C20 0.088(4) 0.170(7) 0.092(3) -0.057(4) 0.023(3) -0.059(5) C21 0.063(2) 0.0524(19) 0.072(2) -0.0199(17) -0.019(2) -0.0142(18) C22 0.082(3) 0.054(2) 0.057(2) -0.0118(16) -0.020(2) -0.022(2) C23 0.146(6) 0.151(6) 0.062(3) -0.036(3) -0.005(3) -0.086(6) C24 0.073(2) 0.0503(18) 0.0544(19) -0.0050(15) -0.0152(18) -0.0203(19) N2 0.083(3) 0.123(4) 0.099(3) -0.063(3) 0.008(3) -0.052(3) O2A 0.087(6) 0.111(7) 0.147(8) -0.063(6) -0.057(6) 0.000(5) C25A 0.060(5) 0.073(5) 0.068(5) -0.030(4) 0.000(4) -0.015(4) C26A 0.058(6) 0.118(10) 0.117(10) -0.088(10) 0.030(5) -0.042(6) C27A 0.064(8) 0.109(10) 0.125(10) -0.073(8) 0.016(6) -0.036(7) C28A 0.063(8) 0.135(10) 0.141(12) -0.086(9) -0.005(7) -0.025(8) C29A 0.092(9) 0.174(13) 0.133(11) -0.103(10) 0.033(6) -0.089(10) C30A 0.109(10) 0.128(10) 0.132(10) -0.071(8) 0.043(7) -0.075(9) C31A 0.093(8) 0.111(9) 0.093(7) -0.051(6) 0.040(5) -0.060(8) O2B 0.159(12) 0.117(9) 0.157(9) -0.074(8) 0.072(9) -0.095(10) C25B 0.054(4) 0.083(6) 0.085(6) -0.054(5) -0.011(4) -0.013(4) C26B 0.055(6) 0.090(8) 0.083(7) -0.054(7) 0.017(5) -0.012(6) C27B 0.080(8) 0.103(9) 0.103(9) -0.070(7) 0.036(6) -0.042(7) C28B 0.114(11) 0.148(12) 0.128(11) -0.084(9) 0.042(7) -0.078(10) C29B 0.092(10) 0.191(14) 0.113(9) -0.100(9) 0.037(6) -0.079(11) C30B 0.073(7) 0.170(11) 0.103(8) -0.087(8) 0.011(6) -0.040(9) C31B 0.056(6) 0.131(9) 0.091(7) -0.067(7) -0.002(5) -0.013(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.335(6) . ? O1 H1 0.82 . ? N1 C7 1.264(5) . ? N1 C8 1.427(4) . ? C1 C6 1.378(6) . ? C1 C2 1.393(5) . ? C1 C7 1.451(5) . ? C2 C3 1.393(6) . ? C3 C4 1.367(10) . ? C3 H3 1.08(7) . ? C4 C5 1.371(10) . ? C4 H4 0.94 . ? C5 C6 1.382(8) . ? C5 H5 0.98(11) . ? C6 H6 0.9496 . ? C7 H7 0.98(4) . ? C8 C9 1.382(5) . ? C8 C14 1.406(5) . ? C9 C11 1.399(5) . ? C9 C10 1.502(5) . ? C10 H10A 0.96 . ? C10 H10B 0.96 . ? C10 H10C 0.96 . ? C10 H10D 0.96 . ? C10 H10E 0.96 . ? C10 H10F 0.96 . ? C11 C12 1.387(6) . ? C11 H11 1.03(7) . ? C12 C13 1.375(6) . ? C12 C16 1.512(5) . ? C13 C14 1.396(5) . ? C13 H13 0.90(4) . ? C14 C15 1.490(6) . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C15 H15D 0.96 . ? C15 H15E 0.96 . ? C15 H15F 0.96 . ? C16 C17 1.521(5) . ? C16 H16A 0.95(7) . ? C16 H16B 1.01(8) . ? C17 C24 1.363(5) . ? C17 C18 1.395(6) . ? C18 C19 1.382(5) . ? C18 H18 0.92(5) . ? C19 C21 1.390(5) . ? C19 C20 1.520(7) . ? C20 H20A 0.96 . ? C20 H20B 0.96 . ? C20 H20C 0.96 . ? C20 H20D 0.96 . ? C20 H20E 0.96 . ? C20 H20F 0.96 . ? C21 C22 1.392(6) . ? C21 N2 1.430(5) . ? C22 C24 1.386(5) . ? C22 C23 1.502(6) . ? C23 H23A 0.96 . ? C23 H23B 0.96 . ? C23 H23C 0.96 . ? C23 H23D 0.96 . ? C23 H23E 0.96 . ? C23 H23F 0.96 . ? C24 H24 1.08(4) . ? N2 C25B 1.073(10) . ? N2 C25A 1.108(9) . ? O2A C27A 1.357(19) . ? O2A H2OA 0.82 . ? C25A C26A 1.411(14) . ? C25A H25A 0.93 . ? C26A C27A 1.42(3) . ? C26A C31A 1.45(2) . ? C27A C28A 1.34(2) . ? C28A C29A 1.42(3) . ? C28A H28A 0.93 . ? C29A C30A 1.37(3) . ? C29A H29A 0.93 . ? C30A C31A 1.302(17) . ? C30A H30A 0.93 . ? C31A H31A 0.93 . ? O2B C27B 1.30(2) . ? O2B H2OB 0.82 . ? C25B C26B 1.470(16) . ? C25B H25B 0.93 . ? C26B C27B 1.37(3) . ? C26B C31B 1.43(2) . ? C27B C28B 1.48(2) . ? C28B C29B 1.41(3) . ? C28B H28B 0.93 . ? C29B C30B 1.28(3) . ? C29B H29B 0.93 . ? C30B C31B 1.357(16) . ? C30B H30B 0.93 . ? C31B H31B 0.93 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1 109.5 . . ? C7 N1 C8 122.8(3) . . ? C6 C1 C2 118.0(4) . . ? C6 C1 C7 121.4(4) . . ? C2 C1 C7 120.6(3) . . ? O1 C2 C1 122.2(4) . . ? O1 C2 C3 117.8(4) . . ? C1 C2 C3 120.0(5) . . ? C4 C3 C2 120.5(6) . . ? C4 C3 H3 116(4) . . ? C2 C3 H3 123(4) . . ? C3 C4 C5 120.1(5) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 119.5(5) . . ? C4 C5 H5 121(5) . . ? C6 C5 H5 119(5) . . ? C1 C6 C5 121.9(5) . . ? C1 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? N1 C7 C1 121.8(3) . . ? N1 C7 H7 126(2) . . ? C1 C7 H7 112(2) . . ? C9 C8 C14 121.7(3) . . ? C9 C8 N1 117.3(3) . . ? C14 C8 N1 120.7(3) . . ? C8 C9 C11 118.1(3) . . ? C8 C9 C10 121.7(3) . . ? C11 C9 C10 120.1(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C10 H10D 109.5 . . ? H10A C10 H10D 141.1 . . ? H10B C10 H10D 56.3 . . ? H10C C10 H10D 56.3 . . ? C9 C10 H10E 109.5 . . ? H10A C10 H10E 56.3 . . ? H10B C10 H10E 141.1 . . ? H10C C10 H10E 56.3 . . ? H10D C10 H10E 109.5 . . ? C9 C10 H10F 109.5 . . ? H10A C10 H10F 56.3 . . ? H10B C10 H10F 56.3 . . ? H10C C10 H10F 141.1 . . ? H10D C10 H10F 109.5 . . ? H10E C10 H10F 109.5 . . ? C12 C11 C9 121.9(4) . . ? C12 C11 H11 122(3) . . ? C9 C11 H11 116(3) . . ? C13 C12 C11 118.4(3) . . ? C13 C12 C16 119.9(4) . . ? C11 C12 C16 121.7(4) . . ? C12 C13 C14 122.3(3) . . ? C12 C13 H13 116(3) . . ? C14 C13 H13 121(3) . . ? C13 C14 C8 117.6(4) . . ? C13 C14 C15 120.5(3) . . ? C8 C14 C15 121.9(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C15 H15D 109.5 . . ? H15A C15 H15D 141.1 . . ? H15B C15 H15D 56.3 . . ? H15C C15 H15D 56.3 . . ? C14 C15 H15E 109.5 . . ? H15A C15 H15E 56.3 . . ? H15B C15 H15E 141.1 . . ? H15C C15 H15E 56.3 . . ? H15D C15 H15E 109.5 . . ? C14 C15 H15F 109.5 . . ? H15A C15 H15F 56.3 . . ? H15B C15 H15F 56.3 . . ? H15C C15 H15F 141.1 . . ? H15D C15 H15F 109.5 . . ? H15E C15 H15F 109.5 . . ? C12 C16 C17 115.2(3) . . ? C12 C16 H16A 105(3) . . ? C17 C16 H16A 102(4) . . ? C12 C16 H16B 109(4) . . ? C17 C16 H16B 114(3) . . ? H16A C16 H16B 110(5) . . ? C24 C17 C18 117.8(3) . . ? C24 C17 C16 119.6(4) . . ? C18 C17 C16 122.6(3) . . ? C19 C18 C17 122.0(3) . . ? C19 C18 H18 121(3) . . ? C17 C18 H18 117(3) . . ? C18 C19 C21 118.3(4) . . ? C18 C19 C20 120.5(4) . . ? C21 C19 C20 121.2(3) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C20 H20D 109.5 . . ? H20A C20 H20D 141.1 . . ? H20B C20 H20D 56.3 . . ? H20C C20 H20D 56.3 . . ? C19 C20 H20E 109.5 . . ? H20A C20 H20E 56.3 . . ? H20B C20 H20E 141.1 . . ? H20C C20 H20E 56.3 . . ? H20D C20 H20E 109.5 . . ? C19 C20 H20F 109.5 . . ? H20A C20 H20F 56.3 . . ? H20B C20 H20F 56.3 . . ? H20C C20 H20F 141.1 . . ? H20D C20 H20F 109.5 . . ? H20E C20 H20F 109.5 . . ? C19 C21 C22 121.1(3) . . ? C19 C21 N2 120.1(4) . . ? C22 C21 N2 118.8(3) . . ? C24 C22 C21 118.1(3) . . ? C24 C22 C23 118.8(4) . . ? C21 C22 C23 123.0(3) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C23 H23D 109.5 . . ? H23A C23 H23D 141.1 . . ? H23B C23 H23D 56.3 . . ? H23C C23 H23D 56.3 . . ? C22 C23 H23E 109.5 . . ? H23A C23 H23E 56.3 . . ? H23B C23 H23E 141.1 . . ? H23C C23 H23E 56.3 . . ? H23D C23 H23E 109.5 . . ? C22 C23 H23F 109.5 . . ? H23A C23 H23F 56.3 . . ? H23B C23 H23F 56.3 . . ? H23C C23 H23F 141.1 . . ? H23D C23 H23F 109.5 . . ? H23E C23 H23F 109.5 . . ? C17 C24 C22 122.7(4) . . ? C17 C24 H24 117.7(19) . . ? C22 C24 H24 119.6(19) . . ? C25B N2 C25A 89.3(7) . . ? C25B N2 C21 135.5(7) . . ? C25A N2 C21 134.5(7) . . ? C27A O2A H2OA 109.5 . . ? N2 C25A C26A 129.0(13) . . ? N2 C25A H25A 115.5 . . ? C26A C25A H25A 115.5 . . ? C25A C26A C27A 127.1(17) . . ? C25A C26A C31A 119.4(17) . . ? C27A C26A C31A 112.9(12) . . ? C28A C27A O2A 121.6(19) . . ? C28A C27A C26A 123.9(17) . . ? O2A C27A C26A 114.5(14) . . ? C27A C28A C29A 118(2) . . ? C27A C28A H28A 120.9 . . ? C29A C28A H28A 120.9 . . ? C30A C29A C28A 120.7(13) . . ? C30A C29A H29A 119.6 . . ? C28A C29A H29A 119.7 . . ? C31A C30A C29A 119.7(14) . . ? C31A C30A H30A 120.2 . . ? C29A C30A H30A 120.2 . . ? C30A C31A C26A 124.6(16) . . ? C30A C31A H31A 117.7 . . ? C26A C31A H31A 117.7 . . ? C27B O2B H2OB 109.5 . . ? N2 C25B C26B 130.5(11) . . ? N2 C25B H25B 114.8 . . ? C26B C25B H25B 114.8 . . ? C27B C26B C31B 124.1(18) . . ? C27B C26B C25B 117.8(15) . . ? C31B C26B C25B 118.0(13) . . ? O2B C27B C26B 125.4(17) . . ? O2B C27B C28B 120.2(17) . . ? C26B C27B C28B 114(2) . . ? C29B C28B C27B 117(2) . . ? C29B C28B H28B 121.4 . . ? C27B C28B H28B 121.4 . . ? C30B C29B C28B 125.3(18) . . ? C30B C29B H29B 117.3 . . ? C28B C29B H29B 117.3 . . ? C29B C30B C31B 120.4(17) . . ? C29B C30B H30B 119.8 . . ? C31B C30B H30B 119.8 . . ? C30B C31B C26B 118.4(16) . . ? C30B C31B H31B 120.8 . . ? C26B C31B H31B 120.8 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O1 -179.5(5) . . . . ? C7 C1 C2 O1 1.7(7) . . . . ? C6 C1 C2 C3 0.5(7) . . . . ? C7 C1 C2 C3 -178.3(4) . . . . ? O1 C2 C3 C4 -179.9(6) . . . . ? C1 C2 C3 C4 0.1(9) . . . . ? C2 C3 C4 C5 -0.1(10) . . . . ? C3 C4 C5 C6 -0.6(10) . . . . ? C2 C1 C6 C5 -1.1(7) . . . . ? C7 C1 C6 C5 177.7(4) . . . . ? C4 C5 C6 C1 1.2(9) . . . . ? C8 N1 C7 C1 177.8(3) . . . . ? C6 C1 C7 N1 -176.5(4) . . . . ? C2 C1 C7 N1 2.3(6) . . . . ? C7 N1 C8 C9 114.4(4) . . . . ? C7 N1 C8 C14 -71.6(4) . . . . ? C14 C8 C9 C11 1.2(5) . . . . ? N1 C8 C9 C11 175.1(3) . . . . ? C14 C8 C9 C10 179.8(3) . . . . ? N1 C8 C9 C10 -6.3(5) . . . . ? C8 C9 C11 C12 -1.0(5) . . . . ? C10 C9 C11 C12 -179.7(4) . . . . ? C9 C11 C12 C13 0.6(5) . . . . ? C9 C11 C12 C16 178.7(3) . . . . ? C11 C12 C13 C14 -0.4(5) . . . . ? C16 C12 C13 C14 -178.5(3) . . . . ? C12 C13 C14 C8 0.5(5) . . . . ? C12 C13 C14 C15 -178.0(4) . . . . ? C9 C8 C14 C13 -0.9(5) . . . . ? N1 C8 C14 C13 -174.7(3) . . . . ? C9 C8 C14 C15 177.5(4) . . . . ? N1 C8 C14 C15 3.8(5) . . . . ? C13 C12 C16 C17 -70.6(6) . . . . ? C11 C12 C16 C17 111.3(5) . . . . ? C12 C16 C17 C24 134.6(5) . . . . ? C12 C16 C17 C18 -45.7(7) . . . . ? C24 C17 C18 C19 -0.5(7) . . . . ? C16 C17 C18 C19 179.8(4) . . . . ? C17 C18 C19 C21 0.4(7) . . . . ? C17 C18 C19 C20 -178.9(5) . . . . ? C18 C19 C21 C22 0.9(7) . . . . ? C20 C19 C21 C22 -179.8(5) . . . . ? C18 C19 C21 N2 -178.5(4) . . . . ? C20 C19 C21 N2 0.8(7) . . . . ? C19 C21 C22 C24 -2.0(6) . . . . ? N2 C21 C22 C24 177.5(4) . . . . ? C19 C21 C22 C23 -178.4(5) . . . . ? N2 C21 C22 C23 1.0(7) . . . . ? C18 C17 C24 C22 -0.6(6) . . . . ? C16 C17 C24 C22 179.1(4) . . . . ? C21 C22 C24 C17 1.8(6) . . . . ? C23 C22 C24 C17 178.5(5) . . . . ? C19 C21 N2 C25B -129.9(9) . . . . ? C22 C21 N2 C25B 50.7(10) . . . . ? C19 C21 N2 C25A 63.2(9) . . . . ? C22 C21 N2 C25A -116.3(8) . . . . ? C25B N2 C25A C26A 2.6(12) . . . . ? C21 N2 C25A C26A 173.5(10) . . . . ? N2 C25A C26A C27A -2(2) . . . . ? N2 C25A C26A C31A -172.5(10) . . . . ? C25A C26A C27A C28A -172.4(14) . . . . ? C31A C26A C27A C28A -1.2(14) . . . . ? C25A C26A C27A O2A 6.7(17) . . . . ? C31A C26A C27A O2A 177.9(12) . . . . ? O2A C27A C28A C29A -179.4(14) . . . . ? C26A C27A C28A C29A -0.3(16) . . . . ? C27A C28A C29A C30A 3(2) . . . . ? C28A C29A C30A C31A -3(2) . . . . ? C29A C30A C31A C26A 2(2) . . . . ? C25A C26A C31A C30A 172.5(12) . . . . ? C27A C26A C31A C30A 0.5(17) . . . . ? C25A N2 C25B C26B -1.7(11) . . . . ? C21 N2 C25B C26B -172.5(8) . . . . ? N2 C25B C26B C27B 6.0(15) . . . . ? N2 C25B C26B C31B -175.3(10) . . . . ? C31B C26B C27B O2B -179.7(13) . . . . ? C25B C26B C27B O2B -1.1(16) . . . . ? C31B C26B C27B C28B -0.2(13) . . . . ? C25B C26B C27B C28B 178.4(10) . . . . ? O2B C27B C28B C29B 178.9(14) . . . . ? C26B C27B C28B C29B -0.7(14) . . . . ? C27B C28B C29B C30B -1(2) . . . . ? C28B C29B C30B C31B 3(2) . . . . ? C29B C30B C31B C26B -3.8(19) . . . . ? C27B C26B C31B C30B 2.4(16) . . . . ? C25B C26B C31B C30B -176.1(10) . . . . ? #===END data_4a _database_code_CSD 220379 _audit_creation_date 2003-05-09 _audit_creation_method 'CrystalStructure v3.00' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 4,4'-methylenebis(N-salicylidene-2,6-diisopropylaniline) ; _chemical_formula_moiety 'C39 H46 N2 O2' _chemical_formula_sum 'C39 H46 N2 O2' _chemical_formula_weight 574.80 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C12/c1 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 _cell_length_a 36.700(4) _cell_length_b 8.747(4) _cell_length_c 10.687(4) _cell_angle_alpha 90 _cell_angle_beta 92.62(2) _cell_angle_gamma 90 _cell_volume 3426.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.6 _cell_measurement_theta_max 15.0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description leaf _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.114 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240.00 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_number 4252 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.9986 _diffrn_measured_fraction_theta_max 0.9986 _reflns_number_total 4187 _reflns_number_gt 1558 _reflns_threshold_expression F^2^>2.0\s(F^2^) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Rigaku AFC-7R' _computing_cell_refinement 'Rigaku AFC-7R' _computing_data_reduction 'CrystalStructure v3.00' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement CRYSTALS _computing_molecular_graphics 'CrystalStructure v3.00' _computing_publication_material 'CrystalStructure v3.00' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0007Fo^2^ + 0.2000\s^2^(Fo) + 0.5000]' _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1558 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.0650 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_shift/su_max 0.0030 _refine_diff_density_max 0.16 _refine_diff_density_min -0.14 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.15911(8) -0.1317(4) 0.8396(3) 0.111(1) Uani 1.00 1 d . . . N1 N 0.12774(7) 0.1189(3) 0.7604(3) 0.0614(9) Uani 1.00 1 d . . . C1 C 0.18327(9) 0.0261(5) 0.6801(4) 0.073(1) Uani 1.00 1 d . . . C2 C 0.1850(1) -0.1014(5) 0.7576(4) 0.086(1) Uani 1.00 1 d . . . C3 C 0.2140(1) -0.2042(6) 0.7494(5) 0.120(2) Uani 1.00 1 d . . . C4 C 0.2407(1) -0.1764(9) 0.6665(6) 0.138(3) Uani 1.00 1 d . . . C5 C 0.2397(1) -0.0501(8) 0.5897(6) 0.124(2) Uani 1.00 1 d . . . C6 C 0.2108(1) 0.0533(6) 0.5944(4) 0.098(2) Uani 1.00 1 d . . . C7 C 0.15290(8) 0.1338(4) 0.6829(4) 0.068(1) Uani 1.00 1 d . . . C8 C 0.09693(7) 0.2187(4) 0.7540(3) 0.056(1) Uani 1.00 1 d . . . C9 C 0.06978(8) 0.1979(4) 0.6595(3) 0.062(1) Uani 1.00 1 d . . . C10 C 0.0718(1) 0.0733(5) 0.5613(4) 0.084(1) Uani 1.00 1 d . . . C11 C 0.0438(1) -0.0521(6) 0.5835(5) 0.118(2) Uani 1.00 1 d . . . C12 C 0.0664(1) 0.1371(6) 0.4296(4) 0.113(2) Uani 1.00 1 d . . . C13 C 0.03910(8) 0.2901(4) 0.6615(3) 0.063(1) Uani 1.00 1 d . . . C14 C 0.03457(7) 0.4000(4) 0.7527(3) 0.057(1) Uani 1.00 1 d . . . C15 C 0.06167(8) 0.4149(4) 0.8475(3) 0.060(1) Uani 1.00 1 d . . . C16 C 0.09290(8) 0.3247(4) 0.8505(3) 0.057(1) Uani 1.00 1 d . . . C17 C 0.12279(9) 0.3392(5) 0.9544(4) 0.075(1) Uani 1.00 1 d . . . C18 C 0.1527(1) 0.4495(6) 0.9128(5) 0.109(2) Uani 1.00 1 d . . . C19 C 0.1090(1) 0.3900(6) 1.0792(4) 0.108(2) Uani 1.00 1 d . . . C20 C 0.00000(1) 0.4961(6) 0.75000(1) 0.066(2) Uani 1.00 1 d . . . H1 H 0.00200(1) 0.5727(6) 0.83000(1) 0.080(2) Uiso 1.00 1 c . . . H2 H 0.01851(8) 0.2904(4) 0.5830(3) 0.076(2) Uiso 1.00 1 c . . . H3 H 0.05723(8) 0.5045(4) 0.9225(3) 0.072(1) Uiso 1.00 1 c . . . H4 H 0.1730(1) 0.4347(6) 0.9961(5) 0.130(2) Uiso 1.00 1 c . . . H5 H 0.1620(1) 0.4157(6) 0.8261(5) 0.130(2) Uiso 1.00 1 c . . . H6 H 0.1370(1) 0.5757(6) 0.9201(5) 0.131(2) Uiso 1.00 1 c . . . H7 H 0.1264(1) 0.3823(6) 1.1512(4) 0.130(2) Uiso 1.00 1 c . . . H8 H 0.1004(1) 0.5093(6) 1.0852(4) 0.130(2) Uiso 1.00 1 c . . . H9 H 0.0874(1) 0.3303(6) 1.1042(4) 0.130(2) Uiso 1.00 1 c . . . H10 H 0.14052(9) 0.2370(5) 0.9646(4) 0.090(2) Uiso 1.00 1 c . . . H11 H 0.15103(8) 0.2432(4) 0.6242(4) 0.082(2) Uiso 1.00 1 c . . . H12 H 0.0400(1) -0.1339(6) 0.5080(5) 0.141(2) Uiso 1.00 1 c . . . H13 H 0.0200(1) 0.0381(6) 0.5730(5) 0.142(2) Uiso 1.00 1 c . . . H14 H 0.0981(1) 0.0314(5) 0.5724(4) 0.100(2) Uiso 1.00 1 c . . . H15 H 0.0395(1) 0.1751(6) 0.4170(4) 0.137(2) Uiso 1.00 1 c . . . H16 H 0.0845(1) 0.2191(6) 0.4071(4) 0.137(2) Uiso 1.00 1 c . . . H17 H 0.0685(1) 0.0461(6) 0.3761(4) 0.137(2) Uiso 1.00 1 c . . . H18 H 0.2060(1) 0.1656(6) 0.5213(4) 0.118(2) Uiso 1.00 1 c . . . H19 H 0.2573(1) -0.0383(8) 0.5138(6) 0.150(3) Uiso 1.00 1 c . . . H20 H 0.2653(1) -0.2421(9) 0.6521(6) 0.166(3) Uiso 1.00 1 c . . . H21 H 0.13725(8) -0.0262(4) 0.8218(3) 0.134(2) Uiso 1.00 1 c . . . H22 H 0.0420(1) -0.0989(6) 0.6430(5) 0.141(2) Uiso 1.00 1 c . . . H23 H 0.2158(1) -0.3126(6) 0.8249(5) 0.143(2) Uiso 1.00 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.092(2) 0.114(3) 0.129(3) 0.029(2) 0.021(2) 0.029(2) N1 0.044(1) 0.066(2) 0.074(2) 0.008(1) 0.004(1) -0.005(2) C1 0.046(2) 0.095(3) 0.079(3) 0.013(2) -0.002(2) -0.022(2) C2 0.065(2) 0.091(3) 0.101(3) 0.028(2) -0.012(2) -0.011(3) C3 0.095(3) 0.125(5) 0.138(4) 0.055(3) -0.011(3) -0.020(4) C4 0.081(3) 0.171(6) 0.162(6) 0.058(4) -0.009(4) -0.068(5) C5 0.058(3) 0.182(6) 0.134(5) 0.021(4) 0.020(3) -0.049(5) C6 0.055(2) 0.137(4) 0.101(3) 0.010(2) 0.012(2) -0.026(3) C7 0.045(2) 0.078(3) 0.082(2) 0.005(2) 0.003(2) -0.008(2) C8 0.036(2) 0.060(2) 0.072(2) 0.001(2) 0.006(1) -0.003(2) C9 0.045(2) 0.066(2) 0.076(2) 0.004(2) 0.006(2) -0.012(2) C10 0.057(2) 0.100(3) 0.093(3) 0.016(2) -0.008(2) -0.035(3) C11 0.161(5) 0.081(3) 0.111(4) -0.012(3) -0.016(3) -0.023(3) C12 0.127(4) 0.121(4) 0.093(3) 0.004(3) 0.033(3) -0.029(3) C13 0.040(2) 0.070(2) 0.080(2) 0.000(2) -0.000(2) -0.010(2) C14 0.034(1) 0.055(2) 0.083(2) -0.003(1) 0.009(1) -0.002(2) C15 0.043(2) 0.060(2) 0.076(2) -0.002(2) 0.010(2) -0.009(2) C16 0.042(2) 0.060(2) 0.068(2) -0.005(2) 0.007(1) -0.003(2) C17 0.057(2) 0.087(3) 0.080(3) 0.006(2) -0.007(2) -0.017(2) C18 0.062(2) 0.149(5) 0.115(4) -0.029(3) -0.011(2) -0.017(3) C19 0.101(3) 0.142(5) 0.081(3) -0.004(3) -0.006(2) -0.032(3) C20 0.039(2) 0.056(3) 0.105(4) 0.0000 0.008(2) 0.0000 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.347(5) yes O1 . H21 . 1.232(6) no N1 . C7 . 1.275(4) yes N1 . C8 . 1.428(4) yes C1 . C2 . 1.389(6) yes C1 . C6 . 1.414(5) yes C1 . C7 . 1.460(5) yes C2 . C3 . 1.401(6) yes C3 . C4 . 1.371(7) yes C3 . H23 . 1.24(1) no C4 . C5 . 1.376(8) yes C4 . H20 . 1.09(1) no C5 . C6 . 1.395(7) yes C5 . H19 . 1.07(1) no C6 . H18 . 1.262(9) no C7 . H11 . 1.145(6) no C8 . C9 . 1.398(4) yes C8 . C16 . 1.400(4) yes C9 . C10 . 1.516(5) yes C9 . C13 . 1.386(4) yes C10 . C11 . 1.527(6) yes C10 . C12 . 1.518(6) yes C10 . H14 . 1.037(6) no C11 . H12 . 1.083(8) no C11 . H13 . 1.179(9) no C11 . H22 . 0.762(5) no C12 . H15 . 1.044(8) no C12 . H16 . 1.015(8) no C12 . H17 . 0.985(7) no C13 . C14 . 1.384(5) yes C13 . H2 . 1.10(1) no C14 . C15 . 1.393(4) yes C14 . C20 . 1.521(4) yes C15 . C16 . 1.391(4) yes C15 . H3 . 1.138(6) no C16 . C17 . 1.530(5) yes C17 . C18 . 1.542(6) yes C17 . C19 . 1.514(5) yes C17 . H10 . 1.108(6) no C18 . H4 . 1.14(1) no C18 . H5 . 1.045(9) no C18 . H6 . 1.249(9) no C19 . H7 . 0.98(1) no C19 . H8 . 1.093(8) no C19 . H9 . 0.995(8) no C20 . H1 . 1.086(5) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . H21 . 103.0(4) no C7 . N1 . C8 . 120.1(3) yes C2 . C1 . C6 . 120.5(4) yes C2 . C1 . C7 . 121.2(4) yes C6 . C1 . C7 . 118.3(4) yes O1 . C2 . C1 . 122.2(3) yes O1 . C2 . C3 . 118.4(5) yes C1 . C2 . C3 . 119.4(5) yes C2 . C3 . C4 . 119.6(6) yes C2 . C3 . H23 . 117.8(6) no C4 . C3 . H23 . 122.4(6) no C3 . C4 . C5 . 121.9(5) yes C3 . C4 . H20 . 128.3(7) no C5 . C4 . H20 . 109.8(7) no C4 . C5 . C6 . 119.9(5) yes C4 . C5 . H19 . 122.1(7) no C6 . C5 . H19 . 117.0(7) no C1 . C6 . C5 . 118.7(5) yes C1 . C6 . H18 . 116.7(5) no C5 . C6 . H18 . 124.5(6) no N1 . C7 . C1 . 121.6(4) yes N1 . C7 . H11 . 114.5(4) no C1 . C7 . H11 . 123.7(4) no N1 . C8 . C9 . 119.5(3) yes N1 . C8 . C16 . 118.6(3) yes C9 . C8 . C16 . 121.5(3) yes C8 . C9 . C10 . 122.6(3) yes C8 . C9 . C13 . 117.7(3) yes C10 . C9 . C13 . 119.6(3) yes C9 . C10 . C11 . 110.8(3) yes C9 . C10 . C12 . 111.7(4) yes C11 . C10 . C12 . 110.4(4) yes C9 . C10 . H14 . 104.4(4) no C11 . C10 . H14 . 111.0(5) no C12 . C10 . H14 . 108.5(5) no C10 . C11 . H12 . 115.1(5) no C10 . C11 . H13 . 90.3(5) no H12 . C11 . H13 . 107.5(6) no C10 . C11 . H22 . 126.9(6) no H12 . C11 . H22 . 104.7(7) no H13 . C11 . H22 . 110.2(7) no C10 . C12 . H15 . 108.6(5) no C10 . C12 . H16 . 114.9(5) no H15 . C12 . H16 . 111.7(6) no C10 . C12 . H17 . 103.4(5) no H15 . C12 . H17 . 106.4(6) no H16 . C12 . H17 . 111.3(6) no C9 . C13 . C14 . 122.6(3) yes C9 . C13 . H2 . 121.2(4) no C14 . C13 . H2 . 115.7(4) no C13 . C14 . C15 . 118.2(3) yes C13 . C14 . C20 . 119.8(3) yes C15 . C14 . C20 . 122.0(3) yes C14 . C15 . C16 . 121.6(3) yes C14 . C15 . H3 . 117.2(4) no C16 . C15 . H3 . 121.2(4) no C8 . C16 . C15 . 118.3(3) yes C8 . C16 . C17 . 119.6(3) yes C15 . C16 . C17 . 122.2(3) yes C16 . C17 . C18 . 109.8(3) yes C16 . C17 . C19 . 114.0(3) yes C18 . C17 . C19 . 109.9(4) yes C16 . C17 . H10 . 113.8(4) no C18 . C17 . H10 . 96.4(4) no C19 . C17 . H10 . 111.6(4) no C17 . C18 . H4 . 98.7(5) no C17 . C18 . H5 . 110.1(5) no H4 . C18 . H5 . 115.6(6) no C17 . C18 . H6 . 101.5(5) no H4 . C18 . H6 . 109.8(5) no H5 . C18 . H6 . 118.4(6) no C17 . C19 . H7 . 116.1(5) no C17 . C19 . H8 . 116.2(5) no H7 . C19 . H8 . 101.4(5) no C17 . C19 . H9 . 112.6(5) no H7 . C19 . H9 . 104.6(6) no H8 . C19 . H9 . 104.5(5) no C14 . C20 . H1 . 107.4(2) no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_site_symmetry_1 _geom_torsion_atom_site_label_2 _geom_torsion_site_symmetry_2 _geom_torsion_atom_site_label_3 _geom_torsion_site_symmetry_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C8 . N1 . C7 . C1 . -174.9(4) yes C7 . N1 . C8 . C9 . 75.4(6) yes C7 . N1 . C8 . C16 . -111.2(5) yes C6 . C1 . C2 . O1 . -179.5(5) yes C6 . C1 . C2 . C3 . -0.7(9) yes C7 . C1 . C2 . O1 . -0.6(8) yes C7 . C1 . C2 . C3 . 178.2(5) yes C2 . C1 . C6 . C5 . -0.2(9) yes C7 . C1 . C6 . C5 . -179.1(5) yes C2 . C1 . C7 . N1 . 3.3(9) yes C6 . C1 . C7 . N1 . -177.8(5) yes O1 . C2 . C3 . C4 . 179.9(6) yes C1 . C2 . C3 . C4 . 1.1(1) yes C2 . C3 . C4 . C5 . -0.5(1) yes C3 . C4 . C5 . C6 . -0.4(1) yes C4 . C5 . C6 . C1 . 0.8(1) yes N1 . C8 . C9 . C10 . -0.7(6) yes N1 . C8 . C9 . C13 . 175.6(4) yes C16 . C8 . C9 . C10 . -173.8(4) yes C16 . C8 . C9 . C13 . 2.4(7) yes N1 . C8 . C16 . C15 . -176.1(4) yes N1 . C8 . C16 . C17 . 4.6(6) yes C9 . C8 . C16 . C15 . -2.9(7) yes C9 . C8 . C16 . C17 . 177.8(4) yes C8 . C9 . C10 . C11 . 108.6(6) yes C8 . C9 . C10 . C12 . -127.9(5) yes C13 . C9 . C10 . C11 . -67.5(7) yes C13 . C9 . C10 . C12 . 56.0(7) yes C8 . C9 . C13 . C14 . -0.1(7) yes C10 . C9 . C13 . C14 . 176.2(4) yes C9 . C13 . C14 . C15 . -1.6(7) yes C9 . C13 . C14 . C20 . -179.4(4) yes C13 . C14 . C15 . C16 . 1.2(7) yes C20 . C14 . C15 . C16 . 178.8(3) yes C14 . C15 . C16 . C8 . 1.0(6) yes C14 . C15 . C16 . C17 . -179.6(4) yes C8 . C16 . C17 . C18 . 85.4(6) yes C8 . C16 . C17 . C19 . -150.8(5) yes C15 . C16 . C17 . C18 . -93.9(6) yes C15 . C16 . C17 . C19 . 29.9(7) yes loop_ _geom_contact_atom_site_label_1 _geom_contact_site_symmetry_1 _geom_contact_atom_site_label_2 _geom_contact_site_symmetry_2 _geom_contact_distance _geom_contact_publ_flag O1 . N1 . 2.599(4) yes O1 . C1 . 2.395(5) yes O1 . C2 . 1.347(5) yes O1 . C3 . 2.360(6) yes O1 . C6 6_555 3.318(6) yes O1 . C7 . 2.865(5) yes O1 . C12 6_555 3.578(6) yes O1 . H6 1_545 2.83(5) no O1 . H7 6_554 3.17(8) no O1 . H10 . 3.57(3) no O1 . H11 6_555 3.22(2) no O1 . H14 6_555 3.5(1) no O1 . H16 6_555 3.0(2) no O1 . H17 6_555 3.4(3) no O1 . H18 6_555 2.6(1) no O1 . H21 . 1.232(6) no O1 . H23 . 2.62(2) no N1 . C1 . 2.390(4) yes N1 . C2 . 2.851(5) yes N1 . C7 . 1.275(4) yes N1 . C8 . 1.428(4) yes N1 . C9 . 2.440(4) yes N1 . C10 . 2.917(5) yes N1 . C16 . 2.432(4) yes N1 . C17 . 2.842(5) yes N1 . C18 . 3.423(6) yes N1 . H5 . 2.95(2) no N1 . H10 . 2.44(2) no N1 . H11 . 2.04(2) no N1 . H14 . 2.37(4) no N1 . H17 6_555 2.9(2) no N1 . H21 . 1.463(8) no C1 . C2 . 1.389(6) yes C1 . C3 . 2.409(7) yes C1 . C4 . 2.761(6) yes C1 . C5 . 2.417(6) yes C1 . C6 . 1.414(5) yes C1 . C7 . 1.460(5) yes C1 . H10 6_554 3.57(9) no C1 . H11 . 2.30(2) no C1 . H14 . 3.28(7) no C1 . H18 . 2.28(3) no C1 . H19 . 3.36(9) no C1 . H20 7_556 3.25(3) no C1 . H21 . 2.36(5) no C1 . H23 . 3.52(4) no C2 . C3 . 1.401(6) yes C2 . C4 . 2.396(7) yes C2 . C5 . 2.790(7) yes C2 . C6 . 2.434(7) yes C2 . C7 . 2.483(6) yes C2 . H7 6_554 3.4(2) no C2 . H11 . 3.54(4) no C2 . H18 . 3.55(4) no C2 . H18 6_555 2.94(4) no C2 . H20 . 3.43(7) no C2 . H21 . 2.02(2) no C2 . H23 . 2.27(2) no C3 . C4 . 1.371(7) yes C3 . C5 . 2.401(9) yes C3 . C6 . 2.795(8) yes C3 . H18 6_555 2.95(3) no C3 . H19 . 3.37(8) no C3 . H20 . 2.22(4) no C3 . H21 . 3.34(5) no C3 . H23 . 1.24(1) no C4 . C5 . 1.376(8) yes C4 . C6 . 2.399(8) yes C4 . H18 . 3.58(5) no C4 . H19 . 2.14(3) no C4 . H19 4_546 3.16(3) no C4 . H20 . 1.09(1) no C4 . H20 4_546 3.48(1) no C4 . H23 . 2.29(4) no C4 . H23 7_556 3.56(4) no C5 . C6 . 1.395(7) yes C5 . H4 7_546 3.4(2) no C5 . H18 . 2.35(3) no C5 . H19 . 1.07(1) no C5 . H20 . 2.02(2) no C5 . H20 4_546 3.16(2) no C5 . H23 . 3.54(5) no C5 . H23 7_556 2.77(5) no C6 . C7 . 2.468(5) yes C6 . H11 . 2.78(2) no C6 . H18 . 1.262(9) no C6 . H19 . 2.11(3) no C6 . H20 . 3.31(4) no C6 . H20 7_556 3.33(4) no C6 . H23 7_556 3.03(3) no C7 . C8 . 2.343(4) yes C7 . C9 . 3.101(4) yes C7 . C10 . 3.238(5) yes C7 . C16 . 3.348(5) yes C7 . H5 . 2.91(2) no C7 . H10 . 3.19(3) no C7 . H11 . 1.145(6) no C7 . H14 . 2.45(5) no C7 . H18 . 2.68(6) no C7 . H20 7_556 3.58(5) no C7 . H21 . 2.14(2) no C8 . C9 . 1.398(4) yes C8 . C10 . 2.557(5) yes C8 . C11 . 3.522(6) yes C8 . C13 . 2.383(4) yes C8 . C14 . 2.784(4) yes C8 . C15 . 2.395(5) yes C8 . C16 . 1.400(4) yes C8 . C17 . 2.532(5) yes C8 . C18 . 3.290(5) yes C8 . H2 . 3.4(1) no C8 . H3 . 3.44(5) no C8 . H5 . 3.02(4) no C8 . H8 6_564 2.99(3) no C8 . H10 . 2.71(7) no C8 . H11 . 2.48(5) no C8 . H12 6_555 3.6(1) no C8 . H14 . 2.54(1) no C8 . H17 6_555 2.88(8) no C8 . H21 . 2.68(2) no C9 . C10 . 1.516(5) yes C9 . C11 . 2.505(6) yes C9 . C12 . 2.510(6) yes C9 . C13 . 1.386(4) yes C9 . C14 . 2.431(5) yes C9 . C15 . 2.790(5) yes C9 . C16 . 2.441(5) yes C9 . H2 . 2.17(3) no C9 . H8 6_564 2.9(1) no C9 . H11 . 3.05(2) no C9 . H12 . 3.48(4) no C9 . H13 . 2.45(3) no C9 . H14 . 2.04(2) no C9 . H15 . 2.78(6) no C9 . H16 . 2.78(3) no C9 . H17 . 3.31(2) no C9 . H17 6_555 3.15(2) no C9 . H21 . 3.55(8) no C9 . H22 . 2.79(2) no C10 . C11 . 1.527(6) yes C10 . C12 . 1.518(6) yes C10 . C13 . 2.509(5) yes C10 . H2 . 2.74(2) no C10 . H11 . 3.31(4) no C10 . H12 . 2.21(2) no C10 . H13 . 1.93(1) no C10 . H14 . 1.037(6) no C10 . H15 . 2.10(4) no C10 . H16 . 2.15(2) no C10 . H17 . 1.99(1) no C10 . H17 6_555 3.53(1) no C10 . H22 . 2.08(2) no C11 . C12 . 2.500(7) yes C11 . C13 . 3.114(6) yes C11 . H2 . 3.14(2) no C11 . H2 2_556 3.52(2) no C11 . H9 6_554 2.9(2) no C11 . H12 . 1.083(8) no C11 . H12 2_556 3.578(8) no C11 . H13 . 1.179(9) no C11 . H13 2_556 2.820(9) no C11 . H14 . 2.13(1) no C11 . H15 . 2.67(2) no C11 . H15 2_556 3.24(2) no C11 . H16 . 3.42(6) no C11 . H17 . 2.58(4) no C11 . H17 6_555 3.22(4) no C11 . H22 . 0.762(5) no C12 . C13 . 3.027(6) yes C12 . H1 6_564 3.6(2) no C12 . H2 . 2.80(6) no C12 . H3 6_564 3.15(5) no C12 . H12 . 2.71(2) no C12 . H13 . 2.50(5) no C12 . H13 2_556 3.52(5) no C12 . H14 . 2.09(4) no C12 . H15 . 1.044(8) no C12 . H16 . 1.015(8) no C12 . H17 . 0.985(7) no C12 . H21 6_554 3.0(2) no C12 . H22 . 3.23(4) no C12 . H22 6_554 3.17(4) no C13 . C14 . 1.384(5) yes C13 . C14 5_556 3.050(4) yes C13 . C15 . 2.383(5) yes C13 . C16 . 2.776(5) yes C13 . C20 . 2.515(5) yes C13 . H1 . 3.38(5) no C13 . H1 5_556 2.90(5) no C13 . H2 . 1.10(1) no C13 . H2 5_556 3.53(1) no C13 . H3 . 3.40(4) no C13 . H3 6_564 3.22(4) no C13 . H8 6_564 3.0(2) no C13 . H13 . 2.49(2) no C13 . H14 . 3.30(4) no C13 . H15 . 2.80(2) no C13 . H16 . 3.31(9) no C13 . H22 . 3.41(2) no C14 . C15 . 1.393(4) yes C14 . C16 . 2.430(4) yes C14 . C20 . 1.521(4) yes C14 . H1 . 2.12(2) no C14 . H1 5_556 2.18(2) no C14 . H2 . 2.11(2) no C14 . H2 5_556 2.85(2) no C14 . H3 . 2.16(3) no C14 . H8 6_564 3.2(2) no C14 . H9 6_564 3.5(1) no C14 . H12 6_555 3.59(3) no C15 . C16 . 1.391(4) yes C15 . C17 . 2.557(5) yes C15 . C18 . 3.395(5) yes C15 . C19 . 2.967(6) yes C15 . C20 . 2.549(3) yes C15 . H1 . 2.59(1) no C15 . H1 5_556 3.25(1) no C15 . H2 . 3.36(8) no C15 . H2 5_556 3.25(8) no C15 . H3 . 1.138(6) no C15 . H6 . 3.17(4) no C15 . H8 . 2.97(7) no C15 . H8 6_564 3.27(7) no C15 . H9 . 2.96(5) no C15 . H9 6_564 3.58(5) no C15 . H10 . 3.47(7) no C15 . H12 6_555 3.12(7) no C15 . H16 6_565 3.36(8) no C16 . C17 . 1.530(5) yes C16 . C18 . 2.513(5) yes C16 . C19 . 2.552(5) yes C16 . H3 . 2.21(2) no C16 . H4 . 3.40(9) no C16 . H5 . 2.68(2) no C16 . H6 . 2.81(3) no C16 . H7 . 3.42(8) no C16 . H7 6_564 3.59(8) no C16 . H8 . 2.98(2) no C16 . H8 6_564 3.21(2) no C16 . H9 . 2.73(2) no C16 . H10 . 2.22(4) no C16 . H11 . 3.4(1) no C16 . H12 6_555 3.1(1) no C16 . H17 6_555 3.38(9) no C16 . H21 . 3.49(2) no C17 . C18 . 1.542(6) yes C17 . C19 . 1.514(5) yes C17 . H3 . 2.81(2) no C17 . H4 . 2.05(2) no C17 . H5 . 2.14(4) no C17 . H6 . 2.17(2) no C17 . H7 . 2.13(1) no C17 . H8 . 2.22(3) no C17 . H9 . 2.11(4) no C17 . H10 . 1.108(6) no C17 . H12 6_555 3.6(3) no C17 . H21 . 3.55(2) no C18 . C19 . 2.502(6) yes C18 . H3 . 3.54(2) no C18 . H4 . 1.14(1) no C18 . H5 . 1.045(9) no C18 . H6 . 1.249(9) no C18 . H7 . 2.83(5) no C18 . H7 6_564 3.27(5) no C18 . H8 . 2.77(7) no C18 . H9 . 3.38(9) no C18 . H10 . 2.00(1) no C18 . H11 . 3.57(2) no C18 . H11 6_565 3.51(2) no C18 . H19 7_556 3.4(3) no C18 . H20 7_556 3.5(2) no C18 . H23 1_565 3.28(7) no C19 . H3 . 2.67(6) no C19 . H4 . 2.58(4) no C19 . H5 . 3.4(1) no C19 . H6 . 2.60(4) no C19 . H7 . 0.98(1) no C19 . H8 . 1.093(8) no C19 . H9 . 0.995(8) no C19 . H10 . 2.18(3) no C19 . H11 6_565 3.6(1) no C19 . H12 6_555 3.4(3) no C20 . H1 . 1.086(5) no C20 . H1 5_556 1.086(5) no C20 . H2 . 2.65(3) no C20 . H2 5_556 2.65(3) no C20 . H3 . 2.73(7) no C20 . H3 5_556 2.73(7) no #===END data_4b _database_code_CSD 220380 _audit_creation_date 2003-05-09 _audit_creation_method 'CrystalStructure v3.00' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 4,4'-methylenebis(N-salicylidene-2,6-diisopropylaniline) ; _chemical_formula_moiety 'C39 H46 N2 O2' _chemical_formula_sum 'C39 H46 N2 O2' _chemical_formula_weight 574.80 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P121/n1 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 _cell_length_a 18.991(4) _cell_length_b 6.010(4) _cell_length_c 31.619(4) _cell_angle_alpha 90 _cell_angle_beta 103.22(1) _cell_angle_gamma 90 _cell_volume 3512.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 12.1 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.087 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240.00 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.663 _diffrn_reflns_number 6062 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.8529 _diffrn_measured_fraction_theta_max 0.8529 _reflns_number_total 5840 _reflns_number_gt 1907 _reflns_threshold_expression F^2^>2.0\s(F^2^) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Rigaku AFC-7R' _computing_cell_refinement 'Rigaku AFC-7R' _computing_data_reduction 'CrystalStructure v3.00' _computing_structure_solution SIR88 _computing_structure_refinement CRYSTALS _computing_molecular_graphics 'CrystalStructure v3.00' _computing_publication_material 'CrystalStructure v3.00' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0007Fo^2^ + 3.2500\s^2^(Fo) + 0.5000]' _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1907 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.1050 _refine_ls_goodness_of_fit_ref 1.189 _refine_ls_shift/su_max 0.0030 _refine_diff_density_max 0.38 _refine_diff_density_min -0.35 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0844(4) -0.087(1) 0.8633(3) 0.103(3) Uani 1.00 1 d . . . O2 O 0.6022(4) -0.319(1) 0.8316(3) 0.098(3) Uani 1.00 1 d . . . N1 N 0.5178(4) -0.003(1) 0.8484(3) 0.059(3) Uani 1.00 1 d . . . N2 N 0.0208(4) 0.180(1) 0.8945(3) 0.057(3) Uani 1.00 1 d . . . C1 C -0.1034(5) 0.279(2) 0.8874(4) 0.059(4) Uani 1.00 1 d . . . C2 C -0.1296(5) 0.076(2) 0.8708(4) 0.066(4) Uani 1.00 1 d . . . C3 C -0.2033(6) 0.037(2) 0.8604(4) 0.100(5) Uani 1.00 1 d . . . C4 C -0.2507(7) 0.199(3) 0.8661(5) 0.096(5) Uani 1.00 1 d . . . C5 C -0.2269(6) 0.400(3) 0.8830(4) 0.088(5) Uani 1.00 1 d . . . C6 C -0.1522(5) 0.445(2) 0.8941(4) 0.078(4) Uani 1.00 1 d . . . C7 C -0.0260(5) 0.325(2) 0.8992(3) 0.059(4) Uani 1.00 1 d . . . C8 C 0.0963(5) 0.236(2) 0.9062(3) 0.055(4) Uani 1.00 1 d . . . C9 C 0.1383(5) 0.136(2) 0.9428(4) 0.064(4) Uani 1.00 1 d . . . C10 C 0.1056(6) -0.010(2) 0.9727(4) 0.083(4) Uani 1.00 1 d . . . C11 C 0.1477(8) -0.220(2) 0.9865(5) 0.138(7) Uani 1.00 1 d . . . C12 C 0.0932(8) 0.120(2) 1.0104(4) 0.123(6) Uani 1.00 1 d . . . C13 C 0.2130(6) 0.189(2) 0.9539(4) 0.075(4) Uani 1.00 1 d . . . C14 C 0.2426(5) 0.328(2) 0.9286(4) 0.080(4) Uani 1.00 1 d . . . C15 C 0.1997(5) 0.422(2) 0.8912(4) 0.072(4) Uani 1.00 1 d . . . C16 C 0.1254(5) 0.375(2) 0.8785(3) 0.061(4) Uani 1.00 1 d . . . C17 C 0.0806(5) 0.470(2) 0.8369(4) 0.073(4) Uani 1.00 1 d . . . C18 C 0.088(1) 0.337(3) 0.7996(5) 0.197(9) Uani 1.00 1 d . . . C19 C 0.0974(8) 0.702(3) 0.8287(6) 0.197(9) Uani 1.00 1 d . . . C20 C 0.5790(5) 0.025(2) 0.7905(3) 0.056(4) Uani 1.00 1 d . . . C21 C 0.6106(5) -0.188(2) 0.7982(4) 0.070(4) Uani 1.00 1 d . . . C22 C 0.6560(6) -0.265(2) 0.7710(4) 0.082(5) Uani 1.00 1 d . . . C23 C 0.6679(7) -0.139(3) 0.7382(4) 0.090(5) Uani 1.00 1 d . . . C24 C 0.6363(7) 0.068(3) 0.7306(4) 0.103(6) Uani 1.00 1 d . . . C25 C 0.5917(5) 0.148(2) 0.7561(4) 0.079(4) Uani 1.00 1 d . . . C26 C 0.5321(5) 0.107(2) 0.8182(4) 0.055(3) Uani 1.00 1 d . . . C27 C 0.4690(5) 0.091(2) 0.8727(4) 0.063(4) Uani 1.00 1 d . . . C28 C 0.3949(5) 0.051(2) 0.8575(3) 0.052(3) Uani 1.00 1 d . . . C29 C 0.3662(5) -0.085(2) 0.8177(4) 0.068(4) Uani 1.00 1 d . . . C30 C 0.3645(9) -0.328(3) 0.8274(6) 0.185(9) Uani 1.00 1 d . . . C31 C 0.2939(7) -0.012(3) 0.7923(5) 0.152(7) Uani 1.00 1 d . . . C32 C 0.3478(5) 0.139(2) 0.8810(3) 0.062(4) Uani 1.00 1 d . . . C33 C 0.3720(5) 0.264(2) 0.9165(4) 0.082(5) Uani 1.00 1 d . . . C34 C 0.4468(5) 0.300(2) 0.9322(4) 0.112(5) Uani 1.00 1 d . . . C35 C 0.4945(5) 0.208(2) 0.9097(4) 0.096(5) Uani 1.00 1 d . . . C36 C 0.5766(6) 0.249(4) 0.9261(6) 0.155(8) Uani 1.00 1 d . . . C37 C 0.6026(8) 0.123(3) 0.9660(9) 0.29(1) Uani 1.00 1 d . . . C38 C 0.5966(7) 0.482(3) 0.9348(5) 0.147(7) Uani 1.00 1 d . . . C39 C 0.3231(4) 0.386(2) 0.9425(4) 0.112(5) Uani 1.00 1 d . . . H1 H -0.2173(6) -0.088(2) 0.8479(4) 0.119(6) Uiso 1.00 1 c . . . H2 H -0.3117(7) 0.219(3) 0.8475(5) 0.114(5) Uiso 1.00 1 c . . . H3 H -0.2528(6) 0.570(3) 0.8890(4) 0.107(5) Uiso 1.00 1 c . . . H4 H 0.2350(6) 0.119(2) 0.9814(4) 0.090(5) Uiso 1.00 1 c . . . H5 H 0.0614(6) -0.099(2) 0.9613(4) 0.099(5) Uiso 1.00 1 c . . . H6 H 0.7034(7) -0.202(3) 0.7165(4) 0.112(6) Uiso 1.00 1 c . . . H7 H 0.6379(7) 0.091(3) 0.7090(4) 0.129(6) Uiso 1.00 1 c . . . H10 H 0.0294(5) 0.445(2) 0.8294(4) 0.088(4) Uiso 1.00 1 c . . . H14 H -0.0262(4) -0.046(1) 0.8810(3) 0.125(4) Uiso 1.00 1 c . . . H17 H 0.3401(4) 0.356(2) 0.9725(4) 0.134(7) Uiso 1.00 1 c . . . H18 H 0.1548(8) 0.173(2) 1.0250(4) 0.159(7) Uiso 1.00 1 c . . . H19 H 0.0695(8) 0.304(2) 1.0089(4) 0.159(7) Uiso 1.00 1 c . . . H20 H 0.0725(8) 0.086(2) 1.0209(4) 0.159(7) Uiso 1.00 1 c . . . H23 H 0.6715(6) -0.433(2) 0.7720(4) 0.104(5) Uiso 1.00 1 c . . . H24 H 0.5144(5) 0.250(2) 0.8055(4) 0.066(4) Uiso 1.00 1 c . . . H27 H 0.2901(5) 0.131(2) 0.8623(3) 0.074(4) Uiso 1.00 1 c . . . H28 H 0.4580(5) 0.331(2) 0.9556(4) 0.133(7) Uiso 1.00 1 c . . . H30 H 0.5819(5) 0.304(2) 0.7556(4) 0.095(5) Uiso 1.00 1 c . . . H8 H -0.1351(5) 0.584(2) 0.9067(4) 0.097(5) Uiso 1.00 1 c . . . H15 H -0.0096(5) 0.465(2) 0.9114(3) 0.072(4) Uiso 1.00 1 c . . . H33 H 0.3998(5) -0.082(2) 0.7996(4) 0.083(4) Uiso 1.00 1 c . . . H34 H 0.6006(6) 0.193(4) 0.9051(6) 0.18(1) Uiso 1.00 1 c . . . H35 H 0.5793(8) 0.176(3) 0.9876(9) 0.30(2) Uiso 1.00 1 c . . . H36 H 0.5921(8) -0.031(3) 0.9611(9) 0.31(2) Uiso 1.00 1 c . . . H37 H 0.6534(8) 0.142(3) 0.9757(9) 0.31(2) Uiso 1.00 1 c . . . H29 H 0.2209(5) 0.520(2) 0.8740(4) 0.088(4) Uiso 1.00 1 c . . . H31 H 0.5999(7) 0.513(3) 0.9647(5) 0.176(9) Uiso 1.00 1 c . . . H38 H 0.6417(7) 0.512(3) 0.9278(5) 0.176(9) Uiso 1.00 1 c . . . H39 H 0.5601(7) 0.572(3) 0.9175(5) 0.176(9) Uiso 1.00 1 c . . . H25 H 0.3310(9) -0.341(3) 0.8455(6) 0.209(9) Uiso 1.00 1 c . . . H26 H 0.3481(9) -0.413(3) 0.8018(6) 0.209(9) Uiso 1.00 1 c . . . H32 H 0.4105(9) -0.381(3) 0.8426(6) 0.209(9) Uiso 1.00 1 c . . . H9 H 0.2994(7) 0.136(3) 0.7828(5) 0.172(8) Uiso 1.00 1 c . . . H40 H 0.2771(7) -0.105(3) 0.7678(5) 0.172(8) Uiso 1.00 1 c . . . H41 H 0.2599(7) -0.013(3) 0.8101(5) 0.172(8) Uiso 1.00 1 c . . . H21 H 0.1266(8) -0.298(2) 1.0067(5) 0.167(7) Uiso 1.00 1 c . . . H22 H 0.1463(8) -0.311(2) 0.9617(5) 0.167(7) Uiso 1.00 1 c . . . H42 H 0.1966(8) -0.185(2) 0.9997(5) 0.167(7) Uiso 1.00 1 c . . . H16 H 0.3277(4) 0.541(2) 0.9375(4) 0.134(7) Uiso 1.00 1 c . . . H12 H 0.072(1) 0.189(3) 0.8017(5) 0.23(1) Uiso 1.00 1 c . . . H13 H 0.061(1) 0.402(3) 0.7734(5) 0.23(1) Uiso 1.00 1 c . . . H43 H 0.138(1) 0.337(3) 0.7994(5) 0.23(1) Uiso 1.00 1 c . . . H11 H 0.1049(8) 0.789(3) 0.8544(6) 0.22(1) Uiso 1.00 1 c . . . H47 H 0.1401(8) 0.702(3) 0.8178(6) 0.22(1) Uiso 1.00 1 c . . . H48 H 0.0585(8) 0.763(3) 0.8075(6) 0.22(1) Uiso 1.00 1 c . . . H44 H 0.5707(4) -0.246(1) 0.8465(3) 0.126(4) Uiso 1.00 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.074(5) 0.079(6) 0.160(9) -0.016(5) 0.033(5) -0.036(6) O2 0.113(6) 0.081(6) 0.122(8) 0.030(5) 0.069(6) 0.022(6) N1 0.052(5) 0.065(6) 0.062(6) -0.002(5) 0.020(4) -0.016(5) N2 0.045(5) 0.060(6) 0.069(6) 0.003(5) 0.018(4) 0.002(5) C1 0.042(6) 0.071(8) 0.069(8) -0.005(6) 0.021(5) 0.008(7) C2 0.052(7) 0.068(9) 0.079(8) -0.016(7) 0.019(6) -0.004(7) C3 0.068(8) 0.11(1) 0.12(1) -0.040(8) 0.021(8) -0.023(9) C4 0.055(7) 0.13(1) 0.10(1) -0.016(9) 0.010(7) -0.00(1) C5 0.049(7) 0.11(1) 0.11(1) 0.012(8) 0.029(7) 0.00(1) C6 0.057(7) 0.080(9) 0.10(1) 0.005(7) 0.033(6) 0.000(8) C7 0.045(6) 0.065(8) 0.069(8) -0.005(6) 0.016(5) 0.012(7) C8 0.044(6) 0.069(8) 0.055(7) 0.013(6) 0.017(5) -0.010(6) C9 0.063(7) 0.073(9) 0.059(8) 0.027(6) 0.021(6) 0.012(7) C10 0.094(8) 0.081(9) 0.071(9) 0.018(8) 0.015(7) 0.030(8) C11 0.20(2) 0.09(1) 0.13(1) 0.04(1) 0.04(1) 0.01(1) C12 0.18(1) 0.12(1) 0.09(1) -0.00(1) 0.09(1) -0.00(1) C13 0.067(7) 0.11(1) 0.052(8) 0.034(7) 0.016(6) 0.001(7) C14 0.045(6) 0.13(1) 0.065(9) 0.012(7) 0.018(6) -0.026(9) C15 0.050(6) 0.11(1) 0.060(8) -0.007(7) 0.023(6) -0.004(8) C16 0.051(6) 0.083(9) 0.052(7) -0.002(6) 0.018(5) 0.002(7) C17 0.059(6) 0.10(1) 0.064(8) -0.004(7) 0.016(6) 0.017(8) C18 0.34(2) 0.17(2) 0.05(1) 0.15(2) 0.00(1) 0.02(1) C19 0.16(2) 0.12(2) 0.25(2) -0.01(1) -0.06(1) 0.11(2) C20 0.050(6) 0.070(9) 0.050(7) -0.007(6) 0.018(5) -0.008(6) C21 0.053(6) 0.081(9) 0.082(9) -0.007(7) 0.027(6) -0.019(8) C22 0.076(7) 0.08(1) 0.10(1) -0.007(7) 0.044(8) -0.031(8) C23 0.081(9) 0.11(1) 0.09(1) -0.015(9) 0.044(8) -0.03(1) C24 0.098(9) 0.14(1) 0.08(1) -0.01(1) 0.049(8) 0.01(1) C25 0.073(7) 0.09(1) 0.077(9) -0.011(7) 0.018(7) 0.005(8) C26 0.047(6) 0.044(7) 0.073(8) -0.003(5) 0.013(6) -0.009(6) C27 0.044(6) 0.074(8) 0.077(8) 0.003(6) 0.028(6) -0.017(7) C28 0.054(6) 0.062(7) 0.041(6) -0.006(5) 0.018(5) -0.015(6) C29 0.054(6) 0.082(9) 0.072(8) 0.002(6) 0.022(6) -0.002(7) C30 0.21(2) 0.08(1) 0.24(2) -0.00(1) -0.02(2) 0.00(1) C31 0.13(1) 0.18(2) 0.12(1) 0.03(1) -0.029(9) -0.07(1) C32 0.044(5) 0.086(9) 0.054(7) -0.001(6) 0.007(5) -0.018(7) C33 0.042(6) 0.13(1) 0.072(9) 0.010(7) 0.017(6) -0.016(9) C34 0.039(6) 0.20(1) 0.09(1) 0.009(8) 0.011(6) -0.08(1) C35 0.042(6) 0.16(1) 0.09(1) -0.002(7) 0.012(6) -0.07(1) C36 0.039(8) 0.25(2) 0.16(2) 0.02(1) -0.001(8) -0.15(2) C37 0.08(1) 0.10(1) 0.58(4) -0.01(1) -0.13(2) 0.06(2) C38 0.09(1) 0.26(2) 0.09(1) -0.08(1) 0.019(8) 0.01(1) C39 0.036(6) 0.20(2) 0.10(1) -0.002(8) 0.018(6) -0.10(1) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.357(12) yes O1 . H14 . 1.14(1) no O2 . C21 . 1.353(13) yes O2 . H44 . 0.95(1) no N1 . C26 . 1.243(11) yes N1 . C27 . 1.447(11) yes N2 . C7 . 1.278(11) yes N2 . C8 . 1.437(11) yes C1 . C2 . 1.376(14) yes C1 . C6 . 1.410(13) yes C1 . C7 . 1.459(12) yes C2 . C3 . 1.382(13) yes C3 . C4 . 1.365(16) yes C3 . H1 . 0.86(2) no C4 . C5 . 1.359(16) yes C4 . H2 . 1.18(2) no C5 . C6 . 1.405(13) yes C5 . H3 . 1.17(3) no C6 . H8 . 0.95(2) no C7 . H15 . 0.95(1) no C8 . C9 . 1.386(13) yes C8 . C16 . 1.408(13) yes C9 . C10 . 1.524(14) yes C9 . C13 . 1.417(13) yes C10 . C11 . 1.506(15) yes C10 . C12 . 1.487(15) yes C10 . H5 . 0.99(2) no C11 . H21 . 0.95(2) no C11 . H22 . 0.95(2) no C11 . H42 . 0.95(2) no C12 . H18 . 1.20(2) no C12 . H19 . 1.19(2) no C12 . H20 . 0.60(1) no C13 . C14 . 1.366(15) yes C13 . H4 . 0.97(2) no C14 . C15 . 1.391(15) yes C14 . C39 . 1.531(13) yes C15 . C16 . 1.405(12) yes C15 . H29 . 0.95(2) no C16 . C17 . 1.508(14) yes C17 . C18 . 1.457(16) yes C17 . C19 . 1.465(16) yes C17 . H10 . 0.96(1) no C18 . H12 . 0.95(2) no C18 . H13 . 0.95(2) no C18 . H43 . 0.95(3) no C19 . H11 . 0.95(3) no C19 . H47 . 0.95(2) no C19 . H48 . 0.95(2) no C20 . C21 . 1.414(14) yes C20 . C25 . 1.382(13) yes C20 . C26 . 1.468(12) yes C21 . C22 . 1.427(13) yes C22 . C23 . 1.347(16) yes C22 . H23 . 1.05(2) no C23 . C24 . 1.374(16) yes C23 . H6 . 1.13(2) no C24 . C25 . 1.384(15) yes C24 . H7 . 0.70(1) no C25 . H30 . 0.95(2) no C26 . H24 . 0.98(1) no C27 . C28 . 1.399(12) yes C27 . C35 . 1.357(13) yes C28 . C29 . 1.495(13) yes C28 . C32 . 1.391(11) yes C29 . C30 . 1.494(16) yes C29 . C31 . 1.490(14) yes C29 . H33 . 0.95(2) no C30 . H25 . 0.95(3) no C30 . H26 . 0.95(2) no C30 . H32 . 0.95(2) no C31 . H9 . 0.95(2) no C31 . H40 . 0.95(2) no C31 . H41 . 0.95(2) no C32 . C33 . 1.342(14) yes C32 . H27 . 1.12(2) no C33 . C34 . 1.411(13) yes C33 . C39 . 1.556(14) yes C34 . C35 . 1.386(13) yes C34 . H28 . 0.75(1) no C35 . C36 . 1.545(15) yes C36 . C37 . 1.46(3) yes C36 . C38 . 1.46(2) yes C36 . H34 . 0.95(3) no C37 . H35 . 0.95(4) no C37 . H36 . 0.95(2) no C37 . H37 . 0.95(2) no C38 . H31 . 0.95(2) no C38 . H38 . 0.95(2) no C38 . H39 . 0.95(2) no C39 . H17 . 0.95(2) no C39 . H16 . 0.95(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . H14 . 109.9(1) no C21 . O2 . H44 . 108.6(1) no C26 . N1 . C27 . 118.5(9) yes C7 . N2 . C8 . 119.2(8) yes C2 . C1 . C6 . 119.5(9) yes C2 . C1 . C7 . 121.3(10) yes C6 . C1 . C7 . 119.2(11) yes O1 . C2 . C1 . 121.2(9) yes O1 . C2 . C3 . 118.9(12) yes C1 . C2 . C3 . 119.9(12) yes C2 . C3 . C4 . 120.7(12) yes C2 . C3 . H1 . 116.5(2) no C4 . C3 . H1 . 122.5(2) no C3 . C4 . C5 . 121.1(11) yes C3 . C4 . H2 . 127.5(2) no C5 . C4 . H2 . 107.7(2) no C4 . C5 . C6 . 119.7(12) yes C4 . C5 . H3 . 136.7(2) no C6 . C5 . H3 . 103.5(1) no C1 . C6 . C5 . 119.2(12) yes C1 . C6 . H8 . 120.7(1) no C5 . C6 . H8 . 120.1(1) no N2 . C7 . C1 . 121.9(10) yes N2 . C7 . H15 . 118.8(1) no C1 . C7 . H15 . 119.3(1) no N2 . C8 . C9 . 117.4(9) yes N2 . C8 . C16 . 119.4(9) yes C9 . C8 . C16 . 122.9(9) yes C8 . C9 . C10 . 122.1(9) yes C8 . C9 . C13 . 117.6(9) yes C10 . C9 . C13 . 120.1(10) yes C9 . C10 . C11 . 113.4(10) yes C9 . C10 . C12 . 110.9(10) yes C11 . C10 . C12 . 112.3(11) yes C9 . C10 . H5 . 121.0(1) no C11 . C10 . H5 . 90.3(1) no C12 . C10 . H5 . 107.4(1) no C10 . C11 . H21 . 109.1(2) no C10 . C11 . H22 . 109.3(2) no H21 . C11 . H22 . 109.5(2) no C10 . C11 . H42 . 109.9(2) no H21 . C11 . H42 . 109.5(2) no H22 . C11 . H42 . 109.5(2) no C10 . C12 . H18 . 97.5(1) no C10 . C12 . H19 . 125.7(2) no H18 . C12 . H19 . 95.3(2) no C10 . C12 . H20 . 120.3(2) no H18 . C12 . H20 . 125.2(2) no H19 . C12 . H20 . 92.8(2) no C9 . C13 . C14 . 120.9(11) yes C9 . C13 . H4 . 109.1(1) no C14 . C13 . H4 . 129.8(1) no C13 . C14 . C15 . 120.5(10) yes C13 . C14 . C39 . 119.4(12) yes C15 . C14 . C39 . 120.1(12) yes C14 . C15 . C16 . 121.0(10) yes C14 . C15 . H29 . 119.7(1) no C16 . C15 . H29 . 119.3(1) no C8 . C16 . C15 . 116.9(10) yes C8 . C16 . C17 . 122.9(9) yes C15 . C16 . C17 . 120.2(9) yes C16 . C17 . C18 . 111.1(10) yes C16 . C17 . C19 . 114.5(11) yes C18 . C17 . C19 . 108.3(13) yes C16 . C17 . H10 . 119.6(1) no C18 . C17 . H10 . 89.3(1) no C19 . C17 . H10 . 110.9(2) no C17 . C18 . H12 . 111.5(2) no C17 . C18 . H13 . 110.4(2) no H12 . C18 . H13 . 109.5(2) no C17 . C18 . H43 . 106.4(2) no H12 . C18 . H43 . 109.5(2) no H13 . C18 . H43 . 109.5(2) no C17 . C19 . H11 . 111.6(2) no C17 . C19 . H47 . 107.7(2) no H11 . C19 . H47 . 109.5(2) no C17 . C19 . H48 . 109.1(2) no H11 . C19 . H48 . 109.5(2) no H47 . C19 . H48 . 109.5(2) no C21 . C20 . C25 . 118.4(10) yes C21 . C20 . C26 . 119.4(10) yes C25 . C20 . C26 . 122.1(11) yes O2 . C21 . C20 . 122.7(9) yes O2 . C21 . C22 . 118.5(12) yes C20 . C21 . C22 . 118.8(12) yes C21 . C22 . C23 . 120.8(13) yes C21 . C22 . H23 . 119.9(1) no C23 . C22 . H23 . 118.1(2) no C22 . C23 . C24 . 120.1(12) yes C22 . C23 . H6 . 120.3(2) no C24 . C23 . H6 . 119.6(2) no C23 . C24 . C25 . 120.9(12) yes C23 . C24 . H7 . 103.8(2) no C25 . C24 . H7 . 131.4(2) no C20 . C25 . C24 . 120.9(12) yes C20 . C25 . H30 . 117.9(1) no C24 . C25 . H30 . 118.5(1) no N1 . C26 . C20 . 123.4(10) yes N1 . C26 . H24 . 132.1(1) no C20 . C26 . H24 . 104.3(1) no N1 . C27 . C28 . 117.8(10) yes N1 . C27 . C35 . 121.0(9) yes C28 . C27 . C35 . 121.2(9) yes C27 . C28 . C29 . 121.8(8) yes C27 . C28 . C32 . 118.1(10) yes C29 . C28 . C32 . 120.1(8) yes C28 . C29 . C30 . 112.5(11) yes C28 . C29 . C31 . 114.0(10) yes C30 . C29 . C31 . 109.8(12) yes C28 . C29 . H33 . 109.3(1) no C30 . C29 . H33 . 101.1(1) no C31 . C29 . H33 . 109.4(1) no C29 . C30 . H25 . 104.7(2) no C29 . C30 . H26 . 111.8(2) no H25 . C30 . H26 . 109.5(2) no C29 . C30 . H32 . 111.8(2) no H25 . C30 . H32 . 109.5(2) no H26 . C30 . H32 . 109.5(2) no C29 . C31 . H9 . 106.9(2) no C29 . C31 . H40 . 111.3(2) no H9 . C31 . H40 . 109.5(2) no C29 . C31 . H41 . 110.2(2) no H9 . C31 . H41 . 109.5(2) no H40 . C31 . H41 . 109.5(2) no C28 . C32 . C33 . 121.4(9) yes C28 . C32 . H27 . 111.8(1) no C33 . C32 . H27 . 124.9(1) no C32 . C33 . C34 . 120.2(10) yes C32 . C33 . C39 . 125.1(9) yes C34 . C33 . C39 . 114.7(11) yes C33 . C34 . C35 . 119.0(12) yes C33 . C34 . H28 . 114.9(2) no C35 . C34 . H28 . 122.5(2) no C27 . C35 . C34 . 120.1(9) yes C27 . C35 . C36 . 120.4(10) yes C34 . C35 . C36 . 119.5(11) yes C35 . C36 . C37 . 108.8(18) yes C35 . C36 . C38 . 114.6(15) yes C37 . C36 . C38 . 108.3(14) yes C35 . C36 . H34 . 108.6(2) no C37 . C36 . H34 . 107.2(2) no C38 . C36 . H34 . 109.1(2) no C36 . C37 . H35 . 108.8(2) no C36 . C37 . H36 . 110.3(2) no H35 . C37 . H36 . 109.5(3) no C36 . C37 . H37 . 109.3(2) no H35 . C37 . H37 . 109.5(3) no H36 . C37 . H37 . 109.5(3) no C36 . C38 . H31 . 109.3(2) no C36 . C38 . H38 . 110.6(2) no H31 . C38 . H38 . 109.5(2) no C36 . C38 . H39 . 108.5(2) no H31 . C38 . H39 . 109.5(2) no H38 . C38 . H39 . 109.5(2) no C14 . C39 . C33 . 114.6(9) yes C14 . C39 . H17 . 109.2(1) no C33 . C39 . H17 . 109.2(1) no C14 . C39 . H16 . 107.5(1) no C33 . C39 . H16 . 106.7(1) no H17 . C39 . H16 . 109.4(2) no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_site_symmetry_1 _geom_torsion_atom_site_label_2 _geom_torsion_site_symmetry_2 _geom_torsion_atom_site_label_3 _geom_torsion_site_symmetry_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C27 . N1 . C26 . C20 . -178.1(1) yes C26 . N1 . C27 . C28 . 88.9(2) yes C26 . N1 . C27 . C35 . -93.5(2) yes C8 . N2 . C7 . C1 . 179.1(1) yes C7 . N2 . C8 . C9 . 109.5(2) yes C7 . N2 . C8 . C16 . -75.6(2) yes C6 . C1 . C2 . O1 . 179.1(1) yes C6 . C1 . C2 . C3 . 0.8(2) yes C7 . C1 . C2 . O1 . -2.3(2) yes C7 . C1 . C2 . C3 . 179.4(1) yes C2 . C1 . C6 . C5 . -1.2(2) yes C7 . C1 . C6 . C5 . -179.8(1) yes C2 . C1 . C7 . N2 . 0.2(2) yes C6 . C1 . C7 . N2 . 178.8(1) yes O1 . C2 . C3 . C4 . -178.0(1) yes C1 . C2 . C3 . C4 . 0.3(3) yes C2 . C3 . C4 . C5 . -1.1(3) yes C3 . C4 . C5 . C6 . 0.8(3) yes C4 . C5 . C6 . C1 . 0.4(3) yes N2 . C8 . C9 . C10 . -6.3(2) yes N2 . C8 . C9 . C13 . 178.9(1) yes C16 . C8 . C9 . C10 . 179.0(1) yes C16 . C8 . C9 . C13 . 4.2(2) yes N2 . C8 . C16 . C15 . -179.1(1) yes N2 . C8 . C16 . C17 . 0.8(2) yes C9 . C8 . C16 . C15 . -4.5(2) yes C9 . C8 . C16 . C17 . 175.4(1) yes C8 . C9 . C10 . C11 . 136.3(2) yes C8 . C9 . C10 . C12 . -96.2(2) yes C13 . C9 . C10 . C11 . -49.0(2) yes C13 . C9 . C10 . C12 . 78.4(2) yes C8 . C9 . C13 . C14 . -2.0(2) yes C10 . C9 . C13 . C14 . -176.9(2) yes C9 . C13 . C14 . C15 . 0.3(2) yes C9 . C13 . C14 . C39 . 178.1(1) yes C13 . C14 . C15 . C16 . -0.6(2) yes C39 . C14 . C15 . C16 . -178.4(1) yes C13 . C14 . C39 . C33 . 103.9(2) yes C15 . C14 . C39 . C33 . -78.3(2) yes C14 . C15 . C16 . C8 . 2.6(2) yes C14 . C15 . C16 . C17 . -177.3(1) yes C8 . C16 . C17 . C18 . -97.8(2) yes C8 . C16 . C17 . C19 . 139.2(2) yes C15 . C16 . C17 . C18 . 82.1(2) yes C15 . C16 . C17 . C19 . -40.9(2) yes C25 . C20 . C21 . O2 . 178.8(1) yes C25 . C20 . C21 . C22 . 1.7(2) yes C26 . C20 . C21 . O2 . -3.0(2) yes C26 . C20 . C21 . C22 . 179.8(1) yes C21 . C20 . C25 . C24 . -2.1(2) yes C26 . C20 . C25 . C24 . 179.8(1) yes C21 . C20 . C26 . N1 . -0.6(2) yes C25 . C20 . C26 . N1 . 177.5(1) yes O2 . C21 . C22 . C23 . -177.9(1) yes C20 . C21 . C22 . C23 . -0.7(2) yes C21 . C22 . C23 . C24 . -0.0(3) yes C22 . C23 . C24 . C25 . -0.3(3) yes C23 . C24 . C25 . C20 . 1.4(3) yes N1 . C27 . C28 . C29 . 0.2(2) yes N1 . C27 . C28 . C32 . 179.0(1) yes C35 . C27 . C28 . C29 . -177.4(1) yes C35 . C27 . C28 . C32 . 1.4(2) yes N1 . C27 . C35 . C34 . 179.3(1) yes N1 . C27 . C35 . C36 . 2.1(2) yes C28 . C27 . C35 . C34 . -3.2(2) yes C28 . C27 . C35 . C36 . 179.6(2) yes C27 . C28 . C29 . C30 . 87.3(2) yes C27 . C28 . C29 . C31 . -146.9(2) yes C32 . C28 . C29 . C30 . -91.5(2) yes C32 . C28 . C29 . C31 . 34.3(2) yes C27 . C28 . C32 . C33 . 2.1(2) yes C29 . C28 . C32 . C33 . -179.1(1) yes C28 . C32 . C33 . C34 . -3.6(2) yes C28 . C32 . C33 . C39 . 174.2(1) yes C32 . C33 . C34 . C35 . 1.7(2) yes C39 . C33 . C34 . C35 . -176.3(1) yes C32 . C33 . C39 . C14 . 8.5(2) yes C34 . C33 . C39 . C14 . -173.6(2) yes C33 . C34 . C35 . C27 . 1.7(2) yes C33 . C34 . C35 . C36 . 178.9(2) yes C27 . C35 . C36 . C37 . -111.4(2) yes C27 . C35 . C36 . C38 . 127.2(2) yes C34 . C35 . C36 . C37 . 71.4(3) yes C34 . C35 . C36 . C38 . -50.0(3) yes loop_ _geom_contact_atom_site_label_1 _geom_contact_site_symmetry_1 _geom_contact_atom_site_label_2 _geom_contact_site_symmetry_2 _geom_contact_distance _geom_contact_publ_flag O1 . N2 . 2.58(1) yes O1 . C1 . 2.381(14) yes O1 . C2 . 1.357(12) yes O1 . C3 . 2.359(15) yes O1 . C6 1_545 3.332(14) yes O1 . C7 . 2.840(13) yes O1 . C24 3_546 3.572(16) yes O1 . H1 . 2.46(4) no O1 . H7 3_546 3.0(1) no O1 . H14 . 1.14(1) no O1 . H8 1_545 2.71(7) no O1 . H15 1_545 3.25(6) no O2 . N1 . 2.62(1) yes O2 . C20 . 2.429(14) yes O2 . C21 . 1.353(13) yes O2 . C22 . 2.390(15) yes O2 . C26 . 2.871(13) yes O2 . C38 1_545 3.501(17) yes O2 . H2 1_645 3.2(3) no O2 . H3 1_645 3.0(5) no O2 . H23 . 2.62(6) no O2 . H24 1_545 3.09(5) no O2 . H30 1_545 3.26(7) no O2 . H38 1_545 3.1(1) no O2 . H39 1_545 3.1(1) no O2 . H44 . 0.95(1) no N1 . C20 . 2.390(12) yes N1 . C21 . 2.854(12) yes N1 . C26 . 1.243(11) yes N1 . C27 . 1.447(11) yes N1 . C28 . 2.437(11) yes N1 . C29 . 2.861(12) yes N1 . C30 . 3.439(18) yes N1 . C35 . 2.440(14) yes N1 . C36 . 2.885(16) yes N1 . H2 1_655 3.5(2) no N1 . H24 . 2.03(3) no N1 . H33 . 2.46(6) no N1 . H34 . 2.40(6) no N1 . H36 . 3.5(1) no N1 . H39 1_545 3.33(8) no N1 . H32 . 3.03(5) no N1 . H44 . 1.78(2) no N2 . C1 . 2.394(12) yes N2 . C2 . 2.852(12) yes N2 . C7 . 1.278(11) yes N2 . C8 . 1.437(11) yes N2 . C9 . 2.413(13) yes N2 . C10 . 2.861(14) yes N2 . C16 . 2.457(12) yes N2 . C17 . 2.933(13) yes N2 . H5 . 2.67(4) no N2 . H10 . 2.64(4) no N2 . H14 . 1.63(2) no N2 . H15 . 1.92(3) no N2 . H12 . 3.29(7) no N2 . H11 1_545 3.26(9) no C1 . C2 . 1.376(14) yes C1 . C3 . 2.387(15) yes C1 . C4 . 2.765(14) yes C1 . C5 . 2.428(14) yes C1 . C6 . 1.410(13) yes C1 . C7 . 1.459(12) yes C1 . H1 . 3.14(6) no C1 . H3 . 3.34(5) no C1 . H6 3_556 3.4(1) no C1 . H7 3_556 3.5(1) no C1 . H10 . 3.58(9) no C1 . H14 . 2.48(3) no C1 . H20 2_557 3.6(2) no C1 . H8 . 2.06(4) no C1 . H15 . 2.09(3) no C1 . H21 2_557 3.5(3) no C2 . C3 . 1.382(13) yes C2 . C4 . 2.388(16) yes C2 . C5 . 2.772(17) yes C2 . C6 . 2.406(17) yes C2 . C7 . 2.472(14) yes C2 . H1 . 1.93(4) no C2 . H2 . 3.48(7) no C2 . H6 3_556 3.1(1) no C2 . H14 . 2.05(3) no C2 . H20 2_557 3.5(3) no C2 . H8 1_545 3.18(6) no C2 . H8 . 3.27(6) no C2 . H15 . 3.31(6) no C3 . C4 . 1.365(16) yes C3 . C5 . 2.371(19) yes C3 . C6 . 2.759(17) yes C3 . H1 . 0.86(2) no C3 . H2 . 2.28(4) no C3 . H3 1_545 3.16(8) no C3 . H3 . 3.51(8) no C3 . H6 3_556 2.9(1) no C3 . H14 . 3.31(6) no C3 . H8 1_545 3.22(7) no C4 . C5 . 1.359(16) yes C4 . C6 . 2.390(17) yes C4 . H1 . 1.97(4) no C4 . H2 . 1.18(2) no C4 . H3 . 2.35(5) no C4 . H6 3_556 3.0(1) no C4 . H8 . 3.25(7) no C4 . H34 1_455 3.3(4) no C5 . C6 . 1.405(13) yes C5 . H1 . 3.15(7) no C5 . H1 1_565 3.29(7) no C5 . H2 . 2.05(4) no C5 . H3 . 1.17(3) no C5 . H6 3_556 3.3(1) no C5 . H8 . 2.05(4) no C5 . H38 1_455 3.2(4) no C6 . C7 . 2.474(13) yes C6 . H1 1_565 3.28(7) no C6 . H2 . 3.34(8) no C6 . H3 . 2.02(3) no C6 . H6 3_556 3.5(1) no C6 . H7 3_556 3.4(1) no C6 . H18 2_567 3.4(4) no C6 . H19 2_567 3.5(2) no C6 . H8 . 0.95(2) no C6 . H15 . 2.64(4) no C6 . H21 2_557 3.2(3) no C7 . C8 . 2.343(12) yes C7 . C9 . 3.311(14) yes C7 . C16 . 3.105(12) yes C7 . C17 . 3.250(13) yes C7 . H5 . 3.41(7) no C7 . H10 . 2.75(6) no C7 . H14 . 2.30(3) no C7 . H19 . 3.5(1) no C7 . H8 . 2.65(4) no C7 . H15 . 0.95(1) no C8 . C9 . 1.386(13) yes C8 . C10 . 2.547(15) yes C8 . C12 . 3.383(15) yes C8 . C13 . 2.397(14) yes C8 . C14 . 2.761(13) yes C8 . C15 . 2.397(13) yes C8 . C16 . 1.408(13) yes C8 . C17 . 2.562(16) yes C8 . C18 . 3.392(18) yes C8 . H4 . 3.2(1) no C8 . H5 . 2.84(5) no C8 . H10 . 2.77(6) no C8 . H14 . 2.84(4) no C8 . H19 . 3.43(6) no C8 . H15 . 2.47(3) no C8 . H29 . 3.26(6) no C8 . H22 1_565 3.26(7) no C8 . H12 . 3.24(6) no C8 . H11 1_545 3.17(8) no C9 . C10 . 1.524(14) yes C9 . C11 . 2.533(17) yes C9 . C12 . 2.480(14) yes C9 . C13 . 1.417(13) yes C9 . C14 . 2.422(15) yes C9 . C15 . 2.800(15) yes C9 . C16 . 2.454(15) yes C9 . H4 . 1.96(4) no C9 . H5 . 2.20(4) no C9 . H14 . 3.5(1) no C9 . H18 . 2.56(4) no C9 . H19 . 2.89(7) no C9 . H20 . 3.03(7) no C9 . H15 . 3.39(6) no C9 . H21 . 3.34(6) no C9 . H22 . 2.75(5) no C9 . H22 1_565 3.37(5) no C9 . H42 . 2.70(5) no C9 . H11 1_545 3.4(1) no C10 . C11 . 1.506(15) yes C10 . C12 . 1.487(15) yes C10 . C13 . 2.549(16) yes C10 . H4 . 2.53(4) no C10 . H5 . 0.99(2) no C10 . H14 . 3.4(1) no C10 . H18 . 2.03(4) no C10 . H19 . 2.39(5) no C10 . H20 . 1.87(4) no C10 . H20 2_557 3.46(4) no C10 . H21 . 2.03(4) no C10 . H22 . 2.03(4) no C10 . H42 . 2.04(4) no C11 . C12 . 2.486(18) yes C11 . C13 . 3.037(19) yes C11 . H4 . 2.66(5) no C11 . H5 . 1.81(4) no C11 . H18 . 2.65(5) no C11 . H19 1_545 3.37(8) no C11 . H20 . 2.71(6) no C11 . H21 . 0.95(2) no C11 . H22 . 0.95(2) no C11 . H42 . 0.95(2) no C12 . C13 . 3.224(15) yes C12 . H4 . 3.04(7) no C12 . H5 . 2.02(4) no C12 . H5 2_557 3.26(4) no C12 . H18 . 1.20(2) no C12 . H19 . 1.19(2) no C12 . H20 . 0.60(1) no C12 . H20 2_557 3.31(1) no C12 . H8 2_567 3.1(2) no C12 . H21 . 2.60(5) no C12 . H21 1_565 3.56(5) no C12 . H22 . 3.29(7) no C12 . H42 . 2.76(6) no C13 . C14 . 1.366(15) yes C13 . C15 . 2.394(16) yes C13 . C16 . 2.809(15) yes C13 . C33 . 3.514(15) yes C13 . C39 . 2.502(16) yes C13 . H4 . 0.97(2) no C13 . H5 . 3.41(6) no C13 . H17 . 2.55(4) no C13 . H18 . 2.72(6) no C13 . H27 . 3.55(8) no C13 . H37 2_657 3.6(2) no C13 . H29 . 3.25(5) no C13 . H22 . 3.29(6) no C13 . H22 1_565 3.29(6) no C13 . H42 . 2.73(5) no C13 . H16 . 3.16(6) no C14 . C15 . 1.391(15) yes C14 . C16 . 2.435(15) yes C14 . C32 . 2.985(14) yes C14 . C33 . 2.598(12) yes C14 . C39 . 1.531(13) yes C14 . H4 . 2.12(4) no C14 . H17 . 2.05(4) no C14 . H27 . 2.73(5) no C14 . H29 . 2.04(4) no C14 . H22 1_565 3.17(9) no C14 . H16 . 2.03(3) no C15 . C16 . 1.405(12) yes C15 . C17 . 2.525(15) yes C15 . C18 . 3.220(19) yes C15 . C19 . 2.961(18) yes C15 . C32 . 3.364(13) yes C15 . C33 . 3.322(13) yes C15 . C39 . 2.533(14) yes C15 . H4 . 3.32(6) no C15 . H10 . 3.4(1) no C15 . H17 . 3.3(1) no C15 . H27 . 2.75(5) no C15 . H29 . 0.95(2) no C15 . H25 1_565 3.5(1) no C15 . H22 1_565 3.1(1) no C15 . H16 . 2.63(6) no C15 . H12 . 3.6(1) no C15 . H43 . 2.92(7) no C15 . H11 . 2.92(6) no C15 . H47 . 2.88(7) no C16 . C17 . 1.508(14) yes C16 . C18 . 2.445(17) yes C16 . C19 . 2.501(18) yes C16 . H10 . 2.15(5) no C16 . H27 . 3.60(6) no C16 . H15 . 3.03(6) no C16 . H29 . 2.04(3) no C16 . H22 1_565 3.19(9) no C16 . H12 . 2.65(6) no C16 . H13 . 3.27(8) no C16 . H43 . 2.57(5) no C16 . H11 . 2.61(5) no C16 . H47 . 2.81(6) no C16 . H48 . 3.29(8) no C17 . C18 . 1.457(16) yes C17 . C19 . 1.465(16) yes C17 . H10 . 0.96(1) no C17 . H15 . 3.21(8) no C17 . H29 . 2.67(6) no C17 . H12 . 2.01(4) no C17 . H13 . 2.00(4) no C17 . H43 . 1.95(5) no C17 . H11 . 2.02(4) no C17 . H47 . 1.97(4) no C17 . H48 . 1.99(4) no C18 . C19 . 2.37(2) yes C18 . H10 . 1.73(4) no C18 . H33 3_556 3.2(1) no C18 . H29 . 3.2(1) no C18 . H12 . 0.95(2) no C18 . H13 . 0.95(2) no C18 . H43 . 0.95(3) no C18 . H11 . 3.20(8) no C18 . H47 . 2.42(6) no C18 . H48 1_545 3.51(6) no C18 . H48 . 2.64(6) no C19 . H10 . 2.02(4) no C19 . H14 1_565 3.5(1) no C19 . H29 . 2.69(7) no C19 . H12 . 3.21(7) no C19 . H12 1_565 3.05(7) no C19 . H13 . 2.49(6) no C19 . H43 . 2.57(6) no C19 . H11 . 0.95(3) no C19 . H47 . 0.95(2) no C19 . H48 . 0.95(2) no C20 . C21 . 1.414(14) yes C20 . C22 . 2.446(15) yes C20 . C23 . 2.799(15) yes C20 . C24 . 2.406(15) yes C20 . C25 . 1.382(13) yes C20 . C26 . 1.468(12) yes C20 . H2 1_655 2.7(5) no C20 . H7 . 3.06(7) no C20 . H23 . 3.39(6) no C20 . H24 . 1.96(3) no C20 . H30 . 2.01(3) no C20 . H33 . 3.54(5) no C20 . H13 3_546 3.0(2) no C20 . H44 . 2.44(3) no C21 . C22 . 1.427(13) yes C21 . C23 . 2.413(17) yes C21 . C24 . 2.768(18) yes C21 . C25 . 2.402(18) yes C21 . C26 . 2.489(14) yes C21 . H1 1_655 3.3(4) no C21 . H2 1_655 3.1(5) no C21 . H6 . 3.44(9) no C21 . H7 . 3.42(7) no C21 . H23 . 2.15(4) no C21 . H24 . 3.25(5) no C21 . H30 1_545 3.33(6) no C21 . H30 . 3.24(6) no C21 . H13 3_546 3.6(3) no C21 . H44 . 1.89(3) no C22 . C23 . 1.347(16) yes C22 . C24 . 2.36(2) yes C22 . C25 . 2.760(18) yes C22 . H1 1_655 3.2(6) no C22 . H6 . 2.15(5) no C22 . H7 . 2.87(6) no C22 . H23 . 1.05(2) no C22 . H30 1_545 2.93(7) no C22 . H44 . 3.18(8) no C23 . C24 . 1.374(16) yes C23 . C25 . 2.398(17) yes C23 . H6 . 1.13(2) no C23 . H7 . 1.69(4) no C23 . H23 . 2.06(4) no C23 . H23 3_656 3.37(4) no C23 . H30 . 3.23(6) no C24 . C25 . 1.384(15) yes C24 . H6 . 2.17(5) no C24 . H6 3_656 3.41(5) no C24 . H7 . 0.70(1) no C24 . H10 3_546 3.4(6) no C24 . H23 . 3.29(7) no C24 . H23 1_565 3.28(7) no C24 . H30 . 2.02(4) no C25 . C26 . 2.494(16) yes C25 . H2 1_655 3.1(8) no C25 . H6 . 3.42(8) no C25 . H7 . 1.92(4) no C25 . H10 3_546 3.4(4) no C25 . H23 1_565 2.92(7) no C25 . H24 . 2.46(5) no C25 . H30 . 0.95(2) no C25 . H13 3_546 3.2(2) no C25 . H48 3_546 3.2(3) no C26 . C27 . 2.314(14) yes C26 . C28 . 3.149(12) yes C26 . C29 . 3.350(13) yes C26 . C35 . 3.194(16) yes C26 . C36 . 3.430(19) yes C26 . H2 1_655 3.0(3) no C26 . H24 . 0.98(1) no C26 . H30 . 2.66(5) no C26 . H33 . 2.69(4) no C26 . H34 . 2.81(8) no C26 . H13 3_546 3.3(3) no C26 . H44 . 2.35(3) no C27 . C28 . 1.399(12) yes C27 . C29 . 2.530(15) yes C27 . C30 . 3.321(19) yes C27 . C32 . 2.393(12) yes C27 . C33 . 2.750(13) yes C27 . C34 . 2.376(15) yes C27 . C35 . 1.357(13) yes C27 . C36 . 2.519(18) yes C27 . C37 . 3.43(2) yes C27 . H24 . 2.65(5) no C27 . H27 . 3.35(5) no C27 . H28 . 3.04(5) no C27 . H33 . 2.60(6) no C27 . H34 . 2.55(5) no C27 . H36 . 3.3(1) no C27 . H39 . 3.50(8) no C27 . H32 . 3.12(6) no C27 . H32 1_565 3.42(6) no C27 . H44 . 3.04(5) no C28 . C29 . 1.495(13) yes C28 . C30 . 2.485(18) yes C28 . C31 . 2.503(16) yes C28 . C32 . 1.391(11) yes C28 . C33 . 2.383(15) yes C28 . C34 . 2.776(15) yes C28 . C35 . 2.401(14) yes C28 . H24 . 3.31(7) no C28 . H27 . 2.09(3) no C28 . H28 . 3.49(8) no C28 . H33 . 2.02(3) no C28 . H25 . 2.64(5) no C28 . H26 . 3.31(7) no C28 . H32 . 2.67(5) no C28 . H32 1_565 3.47(5) no C28 . H9 . 2.68(7) no C28 . H40 . 3.3(1) no C28 . H41 . 2.69(7) no C29 . C30 . 1.494(16) yes C29 . C31 . 1.490(14) yes C29 . C32 . 2.501(15) yes C29 . H24 . 3.55(5) no C29 . H27 . 2.59(5) no C29 . H33 . 0.95(2) no C29 . H25 . 1.96(4) no C29 . H26 . 2.05(4) no C29 . H32 . 2.05(4) no C29 . H9 . 1.99(4) no C29 . H40 . 2.04(5) no C29 . H41 . 2.02(3) no C29 . H13 3_546 3.5(2) no C30 . C31 . 2.44(2) yes C30 . C32 . 3.33(2) yes C30 . H27 . 3.39(7) no C30 . H33 . 1.92(4) no C30 . H29 1_545 3.5(1) no C30 . H25 . 0.95(3) no C30 . H26 . 0.95(2) no C30 . H32 . 0.95(2) no C30 . H9 . 3.24(7) no C30 . H40 . 2.58(7) no C30 . H41 . 2.71(6) no C31 . C32 . 2.903(17) yes C31 . H27 . 2.39(5) no C31 . H33 . 2.02(3) no C31 . H25 . 2.59(6) no C31 . H26 . 2.61(6) no C31 . H26 3_556 3.58(6) no C31 . H32 . 3.28(8) no C31 . H9 . 0.95(2) no C31 . H9 3_546 3.37(2) no C31 . H40 . 0.95(2) no C31 . H40 3_556 3.20(2) no C31 . H41 . 0.95(2) no C31 . H43 3_546 3.56(9) no C32 . C33 . 1.342(14) yes C32 . C34 . 2.386(15) yes C32 . C35 . 2.757(13) yes C32 . C39 . 2.574(15) yes C32 . H17 . 3.21(5) no C32 . H27 . 1.12(2) no C32 . H28 . 3.00(8) no C32 . H33 . 3.24(6) no C32 . H29 . 3.29(5) no C32 . H25 . 3.08(6) no C32 . H25 1_565 3.31(6) no C32 . H32 1_565 3.45(8) no C32 . H9 . 3.03(7) no C32 . H41 . 2.63(7) no C32 . H16 . 3.08(6) no C33 . C34 . 1.411(13) yes C33 . C35 . 2.409(13) yes C33 . C39 . 1.556(14) yes C33 . H17 . 2.07(4) no C33 . H27 . 2.19(5) no C33 . H28 . 1.85(4) no C33 . H29 . 3.26(7) no C33 . H25 1_565 3.24(9) no C33 . H32 1_565 3.4(1) no C33 . H16 . 2.04(4) no C34 . C35 . 1.386(13) yes C34 . C36 . 2.533(15) yes C34 . C37 . 3.095(17) yes C34 . C38 . 3.031(15) yes C34 . C39 . 2.500(12) yes C34 . H17 . 2.65(6) no C34 . H27 . 3.4(1) no C34 . H28 . 0.75(1) no C34 . H34 . 3.29(7) no C34 . H35 . 2.82(8) no C34 . H36 . 3.35(7) no C34 . H31 . 3.13(7) no C34 . H39 . 2.83(6) no C34 . H32 1_565 3.4(1) no C34 . H16 . 2.73(4) no C35 . C36 . 1.545(15) yes C35 . C37 . 2.44(2) yes C35 . C38 . 2.527(19) yes C35 . H24 . 3.41(6) no C35 . H28 . 1.89(4) no C35 . H34 . 2.06(3) no C35 . H35 . 2.62(9) no C35 . H36 . 2.60(7) no C35 . H37 . 3.3(1) no C35 . H31 . 2.96(7) no C35 . H38 . 3.28(6) no C35 . H39 . 2.50(6) no C35 . H32 1_565 3.4(1) no C36 . C37 . 1.46(3) yes C36 . C38 . 1.46(2) yes C36 . H28 . 2.67(6) no C36 . H34 . 0.95(3) no C36 . H35 . 1.98(7) no C36 . H36 . 2.00(6) no C36 . H37 . 1.99(6) no C36 . H31 . 1.99(6) no C36 . H38 . 2.00(5) no C36 . H39 . 1.98(6) no C37 . C38 . 2.36(2) yes C37 . H4 2_657 3.5(2) no C37 . H17 2_657 3.5(1) no C37 . H28 . 2.97(6) no C37 . H34 . 1.96(7) no C37 . H35 . 0.95(4) no C37 . H36 . 0.95(2) no C37 . H37 . 0.95(2) no C37 . H31 . 2.35(6) no C37 . H38 . 2.81(8) no C37 . H39 . 3.12(8) no C38 . H3 1_655 3.5(4) no C38 . H17 2_667 3.1(1) no C38 . H28 . 3.00(6) no C38 . H34 . 1.98(6) no C38 . H35 . 2.55(8) no C38 . H36 . 3.20(8) no C38 . H36 1_565 3.05(8) no C38 . H37 . 2.52(7) no C38 . H31 . 0.95(2) no C38 . H38 . 0.95(2) no C38 . H39 . 0.95(2) no C38 . H44 1_565 3.2(1) no C39 . H4 . 2.80(6) no C39 . H17 . 0.95(2) no C39 . H27 . 2.91(5) no C39 . H28 . 2.52(4) no C39 . H29 . 2.68(7) no C39 . H31 2_667 3.0(1) no C39 . H25 1_565 3.5(1) no C39 . H16 . 0.95(2) no #===END