Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_General _journal_coden_Cambridge 182 _audit_creation_date 'Fri May 18 16:29:25 2001' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # PROCESSING SUMMARY (IUCr Office Use Only) #------------------------------------------------------------------------------ # SUBMISSION DETAILS _publ_contact_author_name 'Miwako Mori' _publ_contact_author_address ; Graduate School of Pharmaceutical Sciences Hokkaido University Sapporo 060-0812 JAPAN ; _publ_contact_author_email ' mori@pharm.hokudai.ac.jp ' _publ_contact_author_fax ' 81-11-706-4982 ' _publ_contact_author_phone ' 81-11-706-4982 ' _publ_contact_letter ; ; _publ_requested_journal ' Chemical Communications ' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #------------------------------------------------------------------------------ # TITLE AND AUTHOR LIST _publ_section_title ; Unexpected Results of Enyne Metathesis Using a Ruthenium Complex Containing an N-Heterocyclic Carbene Ligand ; _publ_section_title_footnote ; ; loop_ _publ_author_name 'Kitamura, Tsuyoshi' 'Mori, Miwako' 'Sato, Yoshihiro' _publ_section_synopsis ; ; #------------------------------------------------------------------------------ # TEXT _publ_section_abstract ; Metathesis of enyne having 1,1-substituted alkene was carried out with the new generation of a ruthenium carbene complex containing an N-heterocyclic carbene ligand gave five- and six-membered cyclic compounds in high yield. ; _publ_section_comment ; ; _publ_section_acknowledgements ; ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (1999). teXsan. Single Crystal Structure Analysis Software. Version 1.10. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; #------------------------------------------------------------------------------ data_master_file_afc7r.xtl _database_code_CSD 161214 #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C19 H20 N4 O8 ' _chemical_formula_moiety 'C19 H20 N4 O8 ' _chemical_formula_weight 432.39 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 11.554(2) _cell_length_b 11.813(2) _cell_length_c 8.2501(9) _cell_angle_alpha 97.89(1) _cell_angle_beta 97.23(1) _cell_angle_gamma 63.57(1) _cell_volume 996.1(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.8 _cell_measurement_theta_max 14.4 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 4796 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 1.0013 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.0013 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.57 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4569 _reflns_number_gt 2038 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1006 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2038 _refine_ls_number_parameters 361 _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0028 _refine_diff_density_max 0.10 _refine_diff_density_min -0.12 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.009(4) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.6577(3) 0.2534(2) -0.0446(3) 0.0714(8) Uani 1.00 d . . . O(2) O 0.8100(2) 0.0561(2) -0.0226(2) 0.0533(6) Uani 1.00 d . . . O(3) O 0.7136(2) -0.0789(2) 0.1826(3) 0.0638(7) Uani 1.00 d . . . O(4) O 0.8366(2) 0.0030(2) 0.3366(3) 0.0575(6) Uani 1.00 d . . . O(5) O 0.6541(3) 0.5151(3) 1.0771(3) 0.0779(9) Uani 1.00 d . . . O(6) O 0.8001(3) 0.5632(2) 1.2172(3) 0.0791(8) Uani 1.00 d . . . O(7) O 1.0256(3) 0.7358(3) 0.9696(4) 0.092(1) Uani 1.00 d . . . O(8) O 1.0186(3) 0.7290(3) 0.7059(4) 0.095(1) Uani 1.00 d . . . N(1) N 0.6746(3) 0.3782(2) 0.6108(3) 0.0513(7) Uani 1.00 d . . . N(2) N 0.6841(3) 0.4417(3) 0.7615(3) 0.0542(8) Uani 1.00 d . . . N(3) N 0.7449(3) 0.5438(3) 1.0870(3) 0.0593(8) Uani 1.00 d . . . N(4) N 0.9900(3) 0.7059(3) 0.8312(5) 0.071(1) Uani 1.00 d . . . C(1) C 0.5730(3) 0.2593(3) 0.4504(3) 0.0426(7) Uani 1.00 d . . . C(2) C 0.4883(3) 0.2072(3) 0.4390(3) 0.0450(8) Uani 1.00 d . . . C(3) C 0.4540(3) 0.1547(3) 0.2783(4) 0.0466(8) Uani 1.00 d . . . C(4) C 0.5151(3) 0.1629(3) 0.1321(4) 0.0475(8) Uani 1.00 d . . . C(5) C 0.6548(3) 0.1438(3) 0.1778(3) 0.0384(7) Uani 1.00 d . . . C(6) C 0.6496(3) 0.2507(3) 0.3095(3) 0.0431(7) Uani 1.00 d . . . C(7) C 0.4237(4) 0.2019(4) 0.5841(5) 0.062(1) Uani 1.00 d . . . C(8) C 0.3673(4) 0.1078(4) 0.2562(6) 0.064(1) Uani 1.00 d . . . C(9) C 0.7078(3) 0.1591(3) 0.0254(3) 0.0429(7) Uani 1.00 d . . . C(10) C 0.7366(3) 0.0095(3) 0.2309(3) 0.0430(7) Uani 1.00 d . . . C(11) C 0.8630(5) 0.0622(4) -0.1704(5) 0.065(1) Uani 1.00 d . . . C(12) C 0.9199(5) -0.1234(5) 0.3874(6) 0.077(1) Uani 1.00 d . . . C(13) C 0.5935(3) 0.3301(3) 0.6008(3) 0.0483(8) Uani 1.00 d . . . C(14) C 0.7585(3) 0.5040(3) 0.7812(3) 0.0467(8) Uani 1.00 d . . . C(15) C 0.7896(3) 0.5574(3) 0.9367(3) 0.0487(8) Uani 1.00 d . . . C(16) C 0.8646(3) 0.6230(3) 0.9519(4) 0.0552(9) Uani 1.00 d . . . C(17) C 0.9113(3) 0.6363(3) 0.8150(4) 0.0552(9) Uani 1.00 d . . . C(18) C 0.8835(4) 0.5856(3) 0.6598(4) 0.0555(9) Uani 1.00 d . . . C(19) C 0.8106(3) 0.5209(3) 0.6444(3) 0.0534(9) Uani 1.00 d . . . H(1) H 0.512(3) 0.106(3) 0.041(4) 0.071(10) Uiso 1.00 calc . . . H(2) H 0.465(3) 0.248(3) 0.095(4) 0.067(9) Uiso 1.00 calc . . . H(3) H 0.739(3) 0.233(3) 0.352(4) 0.062(9) Uiso 1.00 calc . . . H(4) H 0.614(3) 0.332(3) 0.260(4) 0.053(8) Uiso 1.00 calc . . . H(5) H 0.460(4) 0.226(4) 0.682(6) 0.10(1) Uiso 1.00 calc . . . H(6) H 0.334(4) 0.256(4) 0.575(5) 0.09(1) Uiso 1.00 calc . . . H(7) H 0.432(5) 0.118(5) 0.589(6) 0.12(1) Uiso 1.00 calc . . . H(8) H 0.331(4) 0.101(4) 0.346(5) 0.08(1) Uiso 1.00 calc . . . H(9) H 0.342(3) 0.082(3) 0.141(5) 0.073(10) Uiso 1.00 calc . . . H(10) H 0.801(4) 0.069(4) -0.269(6) 0.10(1) Uiso 1.00 calc . . . H(11) H 0.944(4) -0.015(4) -0.179(5) 0.10(1) Uiso 1.00 calc . . . H(12) H 0.869(4) 0.137(4) -0.177(5) 0.10(1) Uiso 1.00 calc . . . H(13) H 0.957(4) -0.181(4) 0.288(6) 0.10(1) Uiso 1.00 calc . . . H(14) H 0.983(5) -0.114(4) 0.449(6) 0.10(1) Uiso 1.00 calc . . . H(15) H 0.859(5) -0.152(5) 0.440(7) 0.149(9) Uiso 1.00 calc . . . H(16) H 0.550(3) 0.339(3) 0.693(4) 0.047(8) Uiso 1.00 calc . . . H(17) H 0.657(3) 0.430(3) 0.848(4) 0.055(9) Uiso 1.00 calc . . . H(18) H 0.882(3) 0.658(3) 1.059(4) 0.058(9) Uiso 1.00 calc . . . H(19) H 0.915(3) 0.605(3) 0.566(4) 0.063(9) Uiso 1.00 calc . . . H(20) H 0.792(3) 0.486(3) 0.543(4) 0.050(8) Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.089(2) 0.064(1) 0.050(1) -0.016(1) 0.019(1) 0.021(1) O(2) 0.055(1) 0.056(1) 0.049(1) -0.020(1) 0.0186(10) 0.0066(10) O(3) 0.066(2) 0.048(1) 0.082(2) -0.029(1) 0.006(1) 0.008(1) O(4) 0.053(1) 0.062(1) 0.049(1) -0.018(1) -0.0066(10) 0.016(1) O(5) 0.101(2) 0.098(2) 0.042(1) -0.051(2) 0.019(1) -0.008(1) O(6) 0.093(2) 0.085(2) 0.034(1) -0.020(2) 0.000(1) -0.007(1) O(7) 0.111(2) 0.086(2) 0.088(2) -0.060(2) -0.016(2) -0.002(2) O(8) 0.124(3) 0.093(2) 0.094(2) -0.069(2) -0.012(2) 0.032(2) N(1) 0.067(2) 0.053(1) 0.032(1) -0.026(1) 0.005(1) -0.003(1) N(2) 0.078(2) 0.058(2) 0.028(1) -0.033(1) 0.010(1) -0.005(1) N(3) 0.070(2) 0.050(2) 0.034(1) -0.006(1) 0.006(1) -0.002(1) N(4) 0.073(2) 0.051(2) 0.084(2) -0.026(2) -0.012(2) 0.011(2) C(1) 0.048(2) 0.043(1) 0.034(1) -0.017(1) 0.006(1) 0.003(1) C(2) 0.044(2) 0.046(2) 0.044(1) -0.016(1) 0.012(1) 0.004(1) C(3) 0.038(2) 0.048(2) 0.050(2) -0.015(1) 0.008(1) 0.000(1) C(4) 0.045(2) 0.051(2) 0.042(1) -0.019(1) 0.002(1) -0.002(1) C(5) 0.041(1) 0.043(1) 0.032(1) -0.019(1) 0.005(1) 0.004(1) C(6) 0.053(2) 0.045(1) 0.034(1) -0.025(1) 0.006(1) -0.002(1) C(7) 0.062(2) 0.076(2) 0.055(2) -0.031(2) 0.021(2) 0.007(2) C(8) 0.054(2) 0.071(2) 0.072(2) -0.033(2) 0.015(2) -0.009(2) C(9) 0.052(2) 0.046(2) 0.033(1) -0.023(1) 0.003(1) 0.001(1) C(10) 0.041(2) 0.052(2) 0.037(1) -0.018(1) 0.009(1) 0.005(1) C(11) 0.079(3) 0.073(3) 0.052(2) -0.038(2) 0.029(2) -0.003(2) C(12) 0.066(3) 0.080(3) 0.067(3) -0.012(2) -0.004(2) 0.033(2) C(13) 0.056(2) 0.053(2) 0.031(1) -0.019(2) 0.005(1) 0.004(1) C(14) 0.057(2) 0.041(1) 0.032(1) -0.014(1) 0.001(1) -0.001(1) C(15) 0.058(2) 0.040(2) 0.032(1) -0.010(1) -0.002(1) 0.000(1) C(16) 0.066(2) 0.038(1) 0.043(2) -0.011(1) -0.008(1) -0.001(1) C(17) 0.056(2) 0.042(2) 0.058(2) -0.015(1) -0.007(2) 0.007(1) C(18) 0.067(2) 0.049(2) 0.045(2) -0.020(2) 0.005(1) 0.006(1) C(19) 0.072(2) 0.049(2) 0.035(1) -0.024(2) 0.005(1) -0.004(1) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution MULTAN88 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(9) 1.195(3) . . yes O(2) C(9) 1.318(3) . . yes O(2) C(11) 1.456(4) . . yes O(3) C(10) 1.194(4) . . yes O(4) C(10) 1.337(3) . . yes O(4) C(12) 1.457(4) . . yes O(5) N(3) 1.230(4) . . yes O(6) N(3) 1.226(3) . . yes O(7) N(4) 1.224(4) . . yes O(8) N(4) 1.223(4) . . yes N(1) N(2) 1.380(3) . . yes N(1) C(13) 1.284(4) . . yes N(2) C(14) 1.341(4) . . yes N(2) H(17) 0.86(3) . . no N(3) C(15) 1.456(4) . . yes N(4) C(17) 1.458(4) . . yes C(1) C(2) 1.357(4) . . yes C(1) C(6) 1.513(4) . . yes C(1) C(13) 1.453(4) . . yes C(2) C(3) 1.470(4) . . yes C(2) C(7) 1.511(4) . . yes C(3) C(4) 1.506(4) . . yes C(3) C(8) 1.329(4) . . yes C(4) C(5) 1.531(4) . . yes C(4) H(1) 0.95(4) . . no C(4) H(2) 0.98(4) . . no C(5) C(6) 1.533(4) . . yes C(5) C(9) 1.531(4) . . yes C(5) C(10) 1.534(4) . . yes C(6) H(3) 0.99(3) . . no C(6) H(4) 0.98(3) . . no C(7) H(5) 0.93(5) . . no C(7) H(6) 0.94(4) . . no C(7) H(7) 0.96(5) . . no C(8) H(8) 0.92(4) . . no C(8) H(9) 1.01(4) . . no C(11) H(10) 1.00(5) . . no C(11) H(11) 0.98(4) . . no C(11) H(12) 0.92(5) . . no C(12) H(13) 1.00(5) . . no C(12) H(14) 0.88(5) . . no C(12) H(15) 1.07(6) . . no C(13) H(16) 0.94(3) . . no C(14) C(15) 1.427(4) . . yes C(14) C(19) 1.420(4) . . yes C(15) C(16) 1.383(5) . . yes C(16) C(17) 1.367(5) . . yes C(16) H(18) 0.96(3) . . no C(17) C(18) 1.401(4) . . yes C(18) C(19) 1.352(5) . . yes C(18) H(19) 0.98(3) . . no C(19) H(20) 0.92(3) . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(9) O(2) C(11) 115.9(3) . 1_555 1_555 yes C(10) O(4) C(12) 114.5(3) . 1_555 1_555 yes N(2) N(1) C(13) 114.0(3) . 1_555 1_555 yes N(1) N(2) C(14) 118.9(3) . 1_555 1_555 yes N(1) N(2) H(17) 121(2) . 1_555 1_555 no C(14) N(2) H(17) 118(2) . 1_555 1_555 no O(5) N(3) O(6) 123.7(3) . 1_555 1_555 yes O(5) N(3) C(15) 118.8(3) . 1_555 1_555 yes O(6) N(3) C(15) 117.5(3) . 1_555 1_555 yes O(7) N(4) O(8) 123.8(4) . 1_555 1_555 yes O(7) N(4) C(17) 118.0(4) . 1_555 1_555 yes O(8) N(4) C(17) 118.2(3) . 1_555 1_555 yes C(2) C(1) C(6) 123.2(3) . 1_555 1_555 yes C(2) C(1) C(13) 121.2(3) . 1_555 1_555 yes C(6) C(1) C(13) 115.7(3) . 1_555 1_555 yes C(1) C(2) C(3) 119.6(3) . 1_555 1_555 yes C(1) C(2) C(7) 123.4(3) . 1_555 1_555 yes C(3) C(2) C(7) 117.1(3) . 1_555 1_555 yes C(2) C(3) C(4) 117.4(3) . 1_555 1_555 yes C(2) C(3) C(8) 123.0(3) . 1_555 1_555 yes C(4) C(3) C(8) 119.4(3) . 1_555 1_555 yes C(3) C(4) C(5) 111.1(2) . 1_555 1_555 yes C(3) C(4) H(1) 113(2) . 1_555 1_555 no C(3) C(4) H(2) 108(2) . 1_555 1_555 no C(5) C(4) H(1) 110(2) . 1_555 1_555 no C(5) C(4) H(2) 107(2) . 1_555 1_555 no H(1) C(4) H(2) 105(2) . 1_555 1_555 no C(4) C(5) C(6) 107.1(2) . 1_555 1_555 yes C(4) C(5) C(9) 107.9(2) . 1_555 1_555 yes C(4) C(5) C(10) 109.3(2) . 1_555 1_555 yes C(6) C(5) C(9) 108.3(2) . 1_555 1_555 yes C(6) C(5) C(10) 114.5(2) . 1_555 1_555 yes C(9) C(5) C(10) 109.5(2) . 1_555 1_555 yes C(1) C(6) C(5) 111.7(2) . 1_555 1_555 yes C(1) C(6) H(3) 108(1) . 1_555 1_555 no C(1) C(6) H(4) 111(1) . 1_555 1_555 no C(5) C(6) H(3) 108(1) . 1_555 1_555 no C(5) C(6) H(4) 110(1) . 1_555 1_555 no H(3) C(6) H(4) 106(2) . 1_555 1_555 no C(2) C(7) H(5) 110(2) . 1_555 1_555 no C(2) C(7) H(6) 110(2) . 1_555 1_555 no C(2) C(7) H(7) 110(2) . 1_555 1_555 no H(5) C(7) H(6) 109(3) . 1_555 1_555 no H(5) C(7) H(7) 108(3) . 1_555 1_555 no H(6) C(7) H(7) 106(3) . 1_555 1_555 no C(3) C(8) H(8) 119(2) . 1_555 1_555 no C(3) C(8) H(9) 118(2) . 1_555 1_555 no H(8) C(8) H(9) 122(3) . 1_555 1_555 no O(1) C(9) O(2) 124.4(3) . 1_555 1_555 yes O(1) C(9) C(5) 122.7(3) . 1_555 1_555 yes O(2) C(9) C(5) 112.8(2) . 1_555 1_555 yes O(3) C(10) O(4) 124.1(3) . 1_555 1_555 yes O(3) C(10) C(5) 123.7(3) . 1_555 1_555 yes O(4) C(10) C(5) 112.2(3) . 1_555 1_555 yes O(2) C(11) H(10) 111(2) . 1_555 1_555 no O(2) C(11) H(11) 105(2) . 1_555 1_555 no O(2) C(11) H(12) 115(2) . 1_555 1_555 no H(10) C(11) H(11) 112(3) . 1_555 1_555 no H(10) C(11) H(12) 97(3) . 1_555 1_555 no H(11) C(11) H(12) 115(3) . 1_555 1_555 no O(4) C(12) H(13) 108(2) . 1_555 1_555 no O(4) C(12) H(14) 103(3) . 1_555 1_555 no O(4) C(12) H(15) 106(2) . 1_555 1_555 no H(13) C(12) H(14) 107(3) . 1_555 1_555 no H(13) C(12) H(15) 110(3) . 1_555 1_555 no H(14) C(12) H(15) 119(4) . 1_555 1_555 no N(1) C(13) C(1) 120.7(3) . 1_555 1_555 yes N(1) C(13) H(16) 119(1) . 1_555 1_555 no C(1) C(13) H(16) 120(1) . 1_555 1_555 no N(2) C(14) C(15) 123.3(3) . 1_555 1_555 yes N(2) C(14) C(19) 120.7(3) . 1_555 1_555 yes C(15) C(14) C(19) 116.0(3) . 1_555 1_555 yes N(3) C(15) C(14) 121.4(3) . 1_555 1_555 yes N(3) C(15) C(16) 116.9(3) . 1_555 1_555 yes C(14) C(15) C(16) 121.7(3) . 1_555 1_555 yes C(15) C(16) C(17) 119.4(3) . 1_555 1_555 yes C(15) C(16) H(18) 118(1) . 1_555 1_555 no C(17) C(16) H(18) 122(1) . 1_555 1_555 no N(4) C(17) C(16) 119.3(3) . 1_555 1_555 yes N(4) C(17) C(18) 119.6(3) . 1_555 1_555 yes C(16) C(17) C(18) 121.1(4) . 1_555 1_555 yes C(17) C(18) C(19) 119.8(3) . 1_555 1_555 yes C(17) C(18) H(19) 116(1) . 1_555 1_555 no C(19) C(18) H(19) 123(1) . 1_555 1_555 no C(14) C(19) C(18) 122.1(3) . 1_555 1_555 yes C(14) C(19) H(20) 117(1) . 1_555 1_555 no C(18) C(19) H(20) 120(1) . 1_555 1_555 no #------------------------------------------------------------------------------ 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 O(1) C(9) O(2) C(11) 0.7(5) 1_555 1_555 1_555 1_555 yes O(1) C(9) C(5) C(4) 57.8(4) 1_555 1_555 1_555 1_555 yes O(1) C(9) C(5) C(6) -57.8(4) 1_555 1_555 1_555 1_555 yes O(1) C(9) C(5) C(10) 176.6(3) 1_555 1_555 1_555 1_555 yes O(2) C(9) C(5) C(4) -119.5(3) 1_555 1_555 1_555 1_555 yes O(2) C(9) C(5) C(6) 124.9(3) 1_555 1_555 1_555 1_555 yes O(2) C(9) C(5) C(10) -0.7(3) 1_555 1_555 1_555 1_555 yes O(3) C(10) O(4) C(12) 1.4(4) 1_555 1_555 1_555 1_555 yes O(3) C(10) C(5) C(4) 28.0(4) 1_555 1_555 1_555 1_555 yes O(3) C(10) C(5) C(6) 148.2(3) 1_555 1_555 1_555 1_555 yes O(3) C(10) C(5) C(9) -90.0(3) 1_555 1_555 1_555 1_555 yes O(4) C(10) C(5) C(4) -152.3(2) 1_555 1_555 1_555 1_555 yes O(4) C(10) C(5) C(6) -32.1(3) 1_555 1_555 1_555 1_555 yes O(4) C(10) C(5) C(9) 89.7(3) 1_555 1_555 1_555 1_555 yes O(5) N(3) C(15) C(14) -18.4(4) 1_555 1_555 1_555 1_555 yes O(5) N(3) C(15) C(16) 162.3(3) 1_555 1_555 1_555 1_555 yes O(6) N(3) C(15) C(14) 162.2(3) 1_555 1_555 1_555 1_555 yes O(6) N(3) C(15) C(16) -17.0(4) 1_555 1_555 1_555 1_555 yes O(7) N(4) C(17) C(16) 9.4(5) 1_555 1_555 1_555 1_555 yes O(7) N(4) C(17) C(18) -171.4(3) 1_555 1_555 1_555 1_555 yes O(8) N(4) C(17) C(16) -171.9(3) 1_555 1_555 1_555 1_555 yes O(8) N(4) C(17) C(18) 7.3(5) 1_555 1_555 1_555 1_555 yes N(1) N(2) C(14) C(15) -170.9(3) 1_555 1_555 1_555 1_555 yes N(1) N(2) C(14) C(19) 9.5(4) 1_555 1_555 1_555 1_555 yes N(1) C(13) C(1) C(2) 179.5(3) 1_555 1_555 1_555 1_555 yes N(1) C(13) C(1) C(6) -1.7(4) 1_555 1_555 1_555 1_555 yes N(2) N(1) C(13) C(1) -179.5(3) 1_555 1_555 1_555 1_555 yes N(2) C(14) C(15) N(3) 2.0(4) 1_555 1_555 1_555 1_555 yes N(2) C(14) C(15) C(16) -178.8(3) 1_555 1_555 1_555 1_555 yes N(2) C(14) C(19) C(18) 178.5(3) 1_555 1_555 1_555 1_555 yes N(3) C(15) C(14) C(19) -178.4(3) 1_555 1_555 1_555 1_555 yes N(3) C(15) C(16) C(17) 178.7(3) 1_555 1_555 1_555 1_555 yes N(4) C(17) C(16) C(15) 179.8(3) 1_555 1_555 1_555 1_555 yes N(4) C(17) C(18) C(19) 179.9(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) -0.5(4) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(8) -176.7(3) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(5) C(4) 52.0(3) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(5) C(9) 168.2(2) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(5) C(10) -69.3(3) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(6) C(5) -18.6(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(5) 36.4(4) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(6) -8.7(4) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(13) 170.0(3) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(6) -61.2(3) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(9) -177.6(3) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(10) 63.4(3) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(7) 178.4(3) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(3) C(8) -147.3(3) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(1) C(13) 162.6(2) 1_555 1_555 1_555 1_555 yes C(5) C(9) O(2) C(11) 178.0(3) 1_555 1_555 1_555 1_555 yes C(5) C(10) O(4) C(12) -178.2(3) 1_555 1_555 1_555 1_555 yes C(6) C(1) C(2) C(7) 172.5(3) 1_555 1_555 1_555 1_555 yes C(7) C(2) C(1) C(13) -8.8(5) 1_555 1_555 1_555 1_555 yes C(7) C(2) C(3) C(8) 2.2(5) 1_555 1_555 1_555 1_555 yes C(13) N(1) N(2) C(14) -174.9(3) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(17) -0.6(5) 1_555 1_555 1_555 1_555 yes C(14) C(19) C(18) C(17) 1.1(5) 1_555 1_555 1_555 1_555 yes C(15) C(14) C(19) C(18) -1.1(5) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) C(18) 0.6(5) 1_555 1_555 1_555 1_555 yes C(16) C(15) C(14) C(19) 0.8(4) 1_555 1_555 1_555 1_555 yes C(16) C(17) C(18) C(19) -0.8(5) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) N(2) 3.051(4) . 1_554 ? O(1) C(13) 3.085(3) . 1_554 ? O(1) H(5) 3.09(5) . 1_554 ? O(1) O(5) 3.100(4) . 1_554 ? O(1) O(5) 3.422(4) . 2_666 ? O(1) N(1) 3.441(3) . 1_554 ? O(2) H(9) 2.89(4) . 2_655 ? O(2) H(11) 2.98(4) . 2_755 ? O(2) O(7) 3.480(4) . 1_544 ? O(3) H(9) 2.66(4) . 2_655 ? O(3) H(7) 2.88(5) . 2_656 ? O(3) H(18) 2.96(3) . 1_544 ? O(3) H(1) 3.11(4) . 2_655 ? O(3) H(6) 3.34(4) . 2_656 ? O(3) C(7) 3.452(4) . 2_656 ? O(3) H(5) 3.53(5) . 2_656 ? O(3) C(16) 3.549(4) . 1_544 ? O(4) H(11) 3.05(4) . 2_755 ? O(4) H(14) 3.17(5) . 2_756 ? O(4) H(10) 3.28(5) . 1_556 ? O(4) H(12) 3.40(4) . 2_755 ? O(5) H(16) 2.96(3) . 2_667 ? O(5) H(2) 2.99(4) . 2_666 ? O(5) H(4) 3.02(3) . 1_556 ? O(5) H(5) 3.24(5) . 2_667 ? O(5) H(17) 3.48(3) . 2_667 ? O(5) O(7) 3.593(4) . 2_767 ? O(6) H(6) 2.58(4) . 2_667 ? O(6) H(20) 2.98(3) . 1_556 ? O(6) N(4) 3.030(4) . 2_767 ? O(6) H(5) 3.06(4) . 2_667 ? O(6) H(19) 3.09(3) . 1_556 ? O(6) C(17) 3.130(4) . 2_767 ? O(6) C(7) 3.241(5) . 2_667 ? O(6) O(8) 3.246(4) . 2_767 ? O(6) C(18) 3.365(4) . 2_767 ? O(6) H(19) 3.41(3) . 2_767 ? O(6) O(7) 3.445(4) . 2_767 ? O(7) H(12) 2.66(5) . 2_766 ? O(7) H(13) 2.76(5) . 1_566 ? O(7) H(11) 3.05(4) . 1_566 ? O(7) N(3) 3.202(4) . 2_767 ? O(7) C(15) 3.300(4) . 2_767 ? O(7) C(11) 3.347(5) . 2_766 ? O(7) C(14) 3.534(4) . 2_767 ? O(7) H(17) 3.54(3) . 2_767 ? O(8) H(15) 2.78(5) . 1_565 ? O(8) H(11) 2.81(4) . 1_566 ? O(8) H(14) 2.88(4) . 1_565 ? O(8) H(3) 3.12(3) . 2_766 ? O(8) C(12) 3.159(5) . 1_565 ? O(8) H(20) 3.19(3) . 2_766 ? O(8) C(11) 3.582(5) . 1_566 ? N(1) H(12) 3.31(4) . 1_556 ? N(1) H(10) 3.51(4) . 1_556 ? N(2) H(4) 3.29(3) . 2_666 ? N(2) H(12) 3.35(4) . 1_556 ? N(2) H(2) 3.39(4) . 2_666 ? N(3) H(2) 3.00(4) . 2_666 ? N(3) N(4) 3.244(4) . 2_767 ? N(3) H(5) 3.26(5) . 2_667 ? N(3) H(6) 3.34(4) . 2_667 ? N(4) H(11) 3.11(4) . 1_566 ? N(4) H(9) 3.54(4) . 2_666 ? C(1) H(10) 3.46(5) . 1_556 ? C(2) H(7) 3.51(5) . 2_656 ? C(2) C(19) 3.585(4) . 2_666 ? C(3) H(7) 3.18(5) . 2_656 ? C(4) H(9) 3.32(4) . 2_655 ? C(4) H(1) 3.42(4) . 2_655 ? C(5) H(9) 3.47(4) . 2_655 ? C(7) H(8) 3.50(4) . 2_656 ? C(7) H(15) 3.54(6) . 2_656 ? C(7) H(7) 3.55(5) . 2_656 ? C(8) H(7) 2.96(5) . 2_656 ? C(8) H(1) 3.22(4) . 2_655 ? C(8) C(17) 3.346(5) . 2_666 ? C(8) H(10) 3.45(5) . 2_655 ? C(8) C(18) 3.531(5) . 2_666 ? C(9) H(9) 3.24(4) . 2_655 ? C(9) H(17) 3.48(3) . 1_554 ? C(9) H(16) 3.50(3) . 1_554 ? C(10) H(9) 3.26(4) . 2_655 ? C(10) H(7) 3.49(5) . 2_656 ? C(11) H(13) 3.27(4) . 2_755 ? C(11) H(14) 3.34(5) . 2_755 ? C(11) H(11) 3.36(4) . 2_755 ? C(11) H(9) 3.52(4) . 2_655 ? C(11) H(14) 3.59(5) . 1_554 ? C(12) H(12) 3.10(4) . 2_755 ? C(12) H(10) 3.40(5) . 1_556 ? C(12) H(11) 3.44(4) . 2_755 ? C(12) H(14) 3.51(5) . 2_756 ? C(13) H(10) 3.18(4) . 1_556 ? C(13) H(12) 3.46(4) . 1_556 ? C(14) H(2) 3.07(4) . 2_666 ? C(15) H(2) 2.82(4) . 2_666 ? C(15) H(18) 3.50(3) . 2_767 ? C(16) C(16) 3.283(6) . 2_767 ? C(16) H(18) 3.30(3) . 2_767 ? C(16) H(9) 3.36(3) . 2_666 ? C(16) H(2) 3.41(3) . 2_666 ? C(17) H(9) 3.32(4) . 2_666 ? C(17) H(8) 3.42(4) . 2_666 ? C(17) H(18) 3.44(3) . 2_767 ? C(18) H(6) 3.03(4) . 2_666 ? C(18) H(19) 3.04(3) . 2_766 ? C(18) H(8) 3.43(4) . 2_666 ? C(19) H(6) 3.11(4) . 2_666 ? C(19) H(19) 3.43(3) . 2_766 ? H(1) H(9) 2.53(5) . 2_655 ? H(1) H(1) 2.62(7) . 2_655 ? H(1) H(5) 3.33(6) . 1_554 ? H(2) H(5) 3.38(6) . 1_554 ? H(2) H(17) 3.41(5) . 2_666 ? H(3) H(14) 3.20(6) . 2_756 ? H(4) H(17) 3.27(4) . 2_666 ? H(4) H(16) 3.48(4) . 2_666 ? H(5) H(8) 3.51(6) . 2_656 ? H(5) H(10) 3.52(6) . 1_556 ? H(6) H(19) 2.79(6) . 2_666 ? H(6) H(15) 2.97(7) . 2_656 ? H(6) H(20) 2.97(5) . 2_666 ? H(7) H(7) 2.8(1) . 2_656 ? H(7) H(8) 2.85(6) . 2_656 ? H(7) H(15) 3.18(8) . 2_656 ? H(7) H(9) 3.44(6) . 2_656 ? H(8) H(15) 2.79(7) . 2_656 ? H(8) H(10) 2.99(6) . 2_655 ? H(8) H(19) 3.42(5) . 2_666 ? H(9) H(10) 3.26(6) . 2_655 ? H(9) H(18) 3.48(4) . 2_666 ? H(10) H(15) 3.19(7) . 1_554 ? H(10) H(14) 3.21(6) . 1_554 ? H(10) H(16) 3.24(5) . 1_554 ? H(10) H(14) 3.32(6) . 2_755 ? H(11) H(11) 3.11(8) . 2_755 ? H(11) H(14) 3.15(6) . 1_554 ? H(11) H(14) 3.24(6) . 2_755 ? H(11) H(13) 3.27(6) . 2_755 ? H(11) H(12) 3.48(6) . 2_755 ? H(11) H(15) 3.57(7) . 1_554 ? H(12) H(13) 2.58(6) . 2_755 ? H(12) H(14) 2.90(6) . 2_755 ? H(12) H(17) 3.23(5) . 1_554 ? H(12) H(16) 3.51(5) . 1_554 ? H(13) H(18) 2.83(6) . 1_544 ? H(14) H(14) 2.89(9) . 2_756 ? H(15) H(19) 2.95(6) . 1_545 ? H(15) H(18) 3.56(6) . 1_544 ? H(18) H(18) 3.59(6) . 2_767 ? H(19) H(19) 2.59(7) . 2_766 ? H(19) H(20) 3.27(5) . 2_766 ? #------------------------------------------------------------------------------