# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Tadashi Mizutani' _publ_contact_author_address ; Department of Molecular Science and Technology Doshisha University Kyotanabe 610-0321 JAPAN ; _publ_contact_author_email tmizutan@mail.doshisha.ac.jp _publ_contact_author_fax ' +81-774-65-6794 ' _publ_contact_author_phone ' +81-774-65-6623 ' _publ_section_title ; A Facile and Versatile Preparation of Bilindiones and Biladienones from Tetraarylporphyrins ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. ; loop_ _publ_author_name 'Tadashi Mizutani' 'Ho-Chol Chang' 'Hirotaka Furukawa' 'Shoji Horii' 'Susumu Kitagawa' 'Shigeyuki Masaoka' ; K.Wada ; 'Takae Yamauchi' #------------------------------------------------------------------------------ data_str848_TPB_a _database_code_depnum_ccdc_archive 'CCDC 251472' _audit_creation_date 'Mon May 10 21:08:00 2004' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C37 H26 N4 O2 ' _chemical_formula_moiety 'C37 H26 N4 O2 ' _chemical_formula_weight 558.64 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 5.905(1) _cell_length_b 22.765(4) _cell_length_c 21.913(4) _cell_angle_alpha 90 _cell_angle_beta 100.031(4) _cell_angle_gamma 90 _cell_volume 2900(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 11049 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 243.2 #------------------------------------------------------------------------------ _exptl_crystal_description Column _exptl_crystal_colour Blue _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.050 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details REQABA _exptl_absorpt_correction_T_min 0.600 _exptl_absorpt_correction_T_max 0.996 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.71 _diffrn_reflns_number 32554 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.9805 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.9805 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 26 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.0 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). ; _reflns_number_total 6541 _reflns_number_gt 4036 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.0659 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 4036 _refine_ls_number_parameters 388 _refine_ls_goodness_of_fit_ref 1.415 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.28 _refine_diff_density_min -0.25 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _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 0.6155(4) 0.0012(1) 0.1741(1) 0.0581(8) Uani 1.00 d . . . O(2) O 1.1753(4) 0.1238(1) 0.1427(1) 0.0515(7) Uani 1.00 d . . . N(1) N 0.5753(4) 0.0796(1) 0.1063(1) 0.0417(8) Uani 1.00 d . . . N(2) N 0.4895(4) 0.2053(1) 0.1045(1) 0.0363(7) Uani 1.00 d . . . N(3) N 0.5805(4) 0.2024(1) 0.2296(1) 0.0401(7) Uani 1.00 d . . . N(4) N 0.9495(4) 0.1388(1) 0.2165(1) 0.0413(8) Uani 1.00 d . . . C(1) C 0.6650(6) 0.0264(2) 0.1288(2) 0.048(1) Uani 1.00 d . . . C(2) C 0.8241(6) 0.0085(2) 0.0876(2) 0.057(1) Uani 1.00 d . . . C(3) C 0.8193(6) 0.0489(2) 0.0433(2) 0.051(1) Uani 1.00 d . . . C(4) C 0.6639(5) 0.0960(1) 0.0536(1) 0.0406(9) Uani 1.00 d . . . C(5) C 0.6284(5) 0.1478(1) 0.0224(1) 0.0384(9) Uani 1.00 d . . . C(6) C 0.5200(5) 0.1985(1) 0.0443(1) 0.0353(8) Uani 1.00 d . . . C(7) C 0.4282(5) 0.2488(1) 0.0127(1) 0.0432(9) Uani 1.00 d . . . C(8) C 0.3345(5) 0.2840(1) 0.0537(2) 0.0436(9) Uani 1.00 d . . . C(9) C 0.3745(5) 0.2562(1) 0.1117(1) 0.0366(8) Uani 1.00 d . . . C(10) C 0.3204(5) 0.2730(1) 0.1705(1) 0.0370(9) Uani 1.00 d . . . C(11) C 0.4075(5) 0.2442(1) 0.2250(1) 0.0396(9) Uani 1.00 d . . . C(12) C 0.3238(6) 0.2467(2) 0.2831(2) 0.050(1) Uani 1.00 d . . . C(13) C 0.4380(6) 0.2055(2) 0.3205(2) 0.052(1) Uani 1.00 d . . . C(14) C 0.6014(5) 0.1791(1) 0.2865(1) 0.0414(9) Uani 1.00 d . . . C(15) C 0.7652(5) 0.1328(1) 0.3074(1) 0.0400(9) Uani 1.00 d . . . C(16) C 0.9241(5) 0.1149(1) 0.2731(1) 0.0405(9) Uani 1.00 d . . . C(17) C 1.0994(5) 0.0702(1) 0.2862(2) 0.0470(10) Uani 1.00 d . . . C(18) C 1.2143(5) 0.0668(2) 0.2387(2) 0.049(1) Uani 1.00 d . . . C(19) C 1.1206(5) 0.1112(1) 0.1929(2) 0.0429(10) Uani 1.00 d . . . C(20) C 0.7092(5) 0.1534(1) -0.0385(1) 0.0403(9) Uani 1.00 d . . . C(21) C 0.6313(6) 0.1145(2) -0.0857(2) 0.049(1) Uani 1.00 d . . . C(22) C 0.7085(6) 0.1177(2) -0.1419(2) 0.056(1) Uani 1.00 d . . . C(23) C 0.8599(7) 0.1603(2) -0.1511(2) 0.068(1) Uani 1.00 d . . . C(24) C 0.9357(8) 0.2000(2) -0.1048(2) 0.084(2) Uani 1.00 d . . . C(25) C 0.8627(6) 0.1964(2) -0.0487(2) 0.063(1) Uani 1.00 d . . . C(26) C 0.1589(5) 0.3227(1) 0.1730(1) 0.0366(9) Uani 1.00 d . . . C(27) C -0.0602(5) 0.3226(1) 0.1377(2) 0.0452(10) Uani 1.00 d . . . C(28) C -0.2110(5) 0.3683(2) 0.1435(2) 0.050(1) Uani 1.00 d . . . C(29) C -0.1457(6) 0.4135(1) 0.1843(2) 0.048(1) Uani 1.00 d . . . C(30) C 0.0721(6) 0.4148(1) 0.2187(2) 0.048(1) Uani 1.00 d . . . C(31) C 0.2237(5) 0.3692(1) 0.2133(2) 0.0443(10) Uani 1.00 d . . . C(32) C 0.7568(6) 0.1026(2) 0.3671(2) 0.048(1) Uani 1.00 d . . . C(33) C 0.7926(8) 0.1320(2) 0.4221(2) 0.074(1) Uani 1.00 d . . . C(34) C 0.7867(10) 0.1028(3) 0.4777(2) 0.098(2) Uani 1.00 d . . . C(35) C 0.7440(9) 0.0457(3) 0.4783(2) 0.099(2) Uani 1.00 d . . . C(36) C 0.7039(8) 0.0139(2) 0.4233(3) 0.089(2) Uani 1.00 d . . . C(37) C 0.7099(7) 0.0427(2) 0.3677(2) 0.064(1) Uani 1.00 d . . . H(1) H 0.4338 0.0975 0.1229 0.0652 Uiso 1.00 d . . . H(2) H 0.5449 0.1776 0.1402 0.0652 Uiso 1.00 d . . . H(3) H 0.8487 0.1709 0.1964 0.0652 Uiso 1.00 d . . . H(4) H 0.9334 -0.0284 0.0974 0.0652 Uiso 1.00 calc . . . H(5) H 0.9428 0.0521 0.0118 0.0652 Uiso 1.00 calc . . . H(6) H 0.4074 0.2614 -0.0378 0.0652 Uiso 1.00 calc . . . H(7) H 0.2399 0.3207 0.0425 0.0652 Uiso 1.00 calc . . . H(8) H 0.2077 0.2725 0.2931 0.0591 Uiso 1.00 calc . . . H(9) H 0.4169 0.1959 0.3614 0.0617 Uiso 1.00 calc . . . H(10) H 1.1255 0.0402 0.3222 0.0652 Uiso 1.00 calc . . . H(11) H 1.3229 0.0358 0.2261 0.0652 Uiso 1.00 calc . . . H(12) H 0.5225 0.0852 -0.0792 0.0584 Uiso 1.00 calc . . . H(13) H 0.6546 0.0893 -0.1742 0.0673 Uiso 1.00 calc . . . H(14) H 0.9128 0.1634 -0.1897 0.0835 Uiso 1.00 calc . . . H(15) H 1.0433 0.2294 -0.1113 0.1006 Uiso 1.00 calc . . . H(16) H 0.9138 0.2251 -0.0174 0.0755 Uiso 1.00 calc . . . H(17) H -0.1061 0.2919 0.1081 0.0542 Uiso 1.00 calc . . . H(18) H -0.3623 0.3679 0.1192 0.0597 Uiso 1.00 calc . . . H(19) H -0.2525 0.4440 0.1887 0.0591 Uiso 1.00 calc . . . H(20) H 0.1177 0.4464 0.2467 0.0575 Uiso 1.00 calc . . . H(21) H 0.3748 0.3701 0.2370 0.0533 Uiso 1.00 calc . . . H(22) H 0.8191 0.1731 0.4226 0.0898 Uiso 1.00 calc . . . H(23) H 0.8166 0.1254 0.5168 0.1167 Uiso 1.00 calc . . . H(24) H 0.7449 0.0260 0.5175 0.1159 Uiso 1.00 calc . . . H(25) H 0.6692 -0.0265 0.4246 0.1059 Uiso 1.00 calc . . . H(26) H 0.6831 0.0205 0.3295 0.0748 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) 0.068(2) 0.048(2) 0.062(2) 0.003(1) 0.021(1) 0.012(1) O(2) 0.046(1) 0.059(2) 0.053(2) 0.000(1) 0.019(1) 0.004(1) N(1) 0.049(2) 0.037(2) 0.042(2) 0.005(1) 0.016(1) -0.001(1) N(2) 0.046(1) 0.033(1) 0.031(1) 0.006(1) 0.012(1) 0.000(1) N(3) 0.049(2) 0.040(2) 0.034(1) 0.008(1) 0.013(1) 0.001(1) N(4) 0.042(1) 0.045(2) 0.039(1) 0.005(1) 0.012(1) 0.003(1) C(1) 0.052(2) 0.040(2) 0.055(2) -0.002(2) 0.015(2) 0.000(2) C(2) 0.066(2) 0.041(2) 0.068(3) 0.010(2) 0.022(2) 0.001(2) C(3) 0.056(2) 0.044(2) 0.060(2) 0.006(2) 0.023(2) -0.009(2) C(4) 0.042(2) 0.042(2) 0.040(2) 0.000(1) 0.015(1) -0.007(2) C(5) 0.038(2) 0.042(2) 0.037(2) -0.001(1) 0.010(1) -0.006(1) C(6) 0.037(2) 0.038(2) 0.032(2) -0.003(1) 0.011(1) -0.003(1) C(7) 0.047(2) 0.046(2) 0.038(2) 0.003(2) 0.013(1) 0.003(2) C(8) 0.046(2) 0.038(2) 0.047(2) 0.004(1) 0.010(2) 0.004(2) C(9) 0.040(2) 0.034(2) 0.038(2) 0.002(1) 0.011(1) -0.001(1) C(10) 0.040(2) 0.033(2) 0.039(2) 0.000(1) 0.011(1) 0.000(1) C(11) 0.048(2) 0.035(2) 0.038(2) 0.005(1) 0.015(1) -0.002(1) C(12) 0.066(2) 0.048(2) 0.042(2) 0.015(2) 0.022(2) -0.002(2) C(13) 0.065(2) 0.055(2) 0.039(2) 0.010(2) 0.023(2) 0.000(2) C(14) 0.051(2) 0.039(2) 0.035(2) 0.002(1) 0.011(2) -0.002(1) C(15) 0.049(2) 0.035(2) 0.036(2) -0.003(1) 0.009(1) -0.004(1) C(16) 0.045(2) 0.039(2) 0.038(2) -0.001(1) 0.008(1) 0.000(1) C(17) 0.047(2) 0.042(2) 0.052(2) 0.001(2) 0.010(2) 0.006(2) C(18) 0.046(2) 0.042(2) 0.060(2) 0.005(2) 0.015(2) 0.003(2) C(19) 0.038(2) 0.045(2) 0.048(2) -0.006(1) 0.015(2) -0.001(2) C(20) 0.045(2) 0.046(2) 0.033(2) 0.001(2) 0.016(1) -0.007(2) C(21) 0.055(2) 0.051(2) 0.044(2) -0.010(2) 0.015(2) -0.005(2) C(22) 0.069(2) 0.060(2) 0.041(2) -0.007(2) 0.015(2) -0.010(2) C(23) 0.084(3) 0.080(3) 0.051(2) -0.020(2) 0.041(2) -0.015(2) C(24) 0.097(3) 0.101(4) 0.066(3) -0.051(3) 0.051(3) -0.032(3) C(25) 0.070(2) 0.075(3) 0.052(2) -0.034(2) 0.031(2) -0.027(2) C(26) 0.041(2) 0.034(2) 0.036(2) 0.002(1) 0.011(1) 0.001(1) C(27) 0.049(2) 0.039(2) 0.048(2) 0.000(2) 0.009(2) -0.008(2) C(28) 0.044(2) 0.047(2) 0.056(2) 0.002(2) 0.005(2) -0.005(2) C(29) 0.051(2) 0.035(2) 0.062(2) 0.008(2) 0.017(2) -0.002(2) C(30) 0.060(2) 0.035(2) 0.049(2) 0.000(2) 0.013(2) -0.008(2) C(31) 0.047(2) 0.043(2) 0.043(2) -0.003(2) 0.008(2) -0.004(2) C(32) 0.055(2) 0.055(2) 0.035(2) 0.010(2) 0.011(2) 0.005(2) C(33) 0.103(3) 0.080(3) 0.040(2) 0.005(3) 0.013(2) 0.003(2) C(34) 0.122(4) 0.130(5) 0.045(3) 0.005(4) 0.020(3) 0.009(3) C(35) 0.103(4) 0.143(6) 0.056(3) 0.017(4) 0.026(3) 0.047(4) C(36) 0.087(3) 0.088(4) 0.095(4) 0.002(3) 0.024(3) 0.047(3) C(37) 0.068(2) 0.063(3) 0.063(3) 0.004(2) 0.015(2) 0.013(2) #------------------------------------------------------------------------------ _computing_data_collection CRYSTALCLEAR _computing_cell_refinement CRYSTALCLEAR _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR97 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _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(1) 1.226(4) . . yes O(2) C(19) 1.233(4) . . yes N(1) C(1) 1.378(4) . . yes N(1) C(4) 1.399(4) . . yes N(2) C(6) 1.370(3) . . yes N(2) C(9) 1.367(4) . . yes N(3) C(11) 1.387(4) . . yes N(3) C(14) 1.340(4) . . yes N(4) C(16) 1.385(4) . . yes N(4) C(19) 1.366(4) . . yes C(1) C(2) 1.469(4) . . yes C(2) C(3) 1.334(5) . . yes C(3) C(4) 1.453(4) . . yes C(4) C(5) 1.361(4) . . yes C(5) C(6) 1.444(4) . . yes C(5) C(20) 1.497(4) . . yes C(6) C(7) 1.399(4) . . yes C(7) C(8) 1.388(4) . . yes C(8) C(9) 1.402(4) . . yes C(9) C(10) 1.432(4) . . yes C(10) C(11) 1.382(4) . . yes C(10) C(26) 1.487(4) . . yes C(11) C(12) 1.445(4) . . yes C(12) C(13) 1.345(5) . . yes C(13) C(14) 1.448(4) . . yes C(14) C(15) 1.449(4) . . yes C(15) C(16) 1.362(4) . . yes C(15) C(32) 1.488(4) . . yes C(16) C(17) 1.445(4) . . yes C(17) C(18) 1.338(4) . . yes C(18) C(19) 1.465(5) . . yes C(20) C(21) 1.379(4) . . yes C(20) C(25) 1.380(4) . . yes C(21) C(22) 1.387(4) . . yes C(22) C(23) 1.357(5) . . yes C(23) C(24) 1.374(5) . . yes C(24) C(25) 1.375(5) . . yes C(26) C(27) 1.388(4) . . yes C(26) C(31) 1.388(4) . . yes C(27) C(28) 1.390(4) . . yes C(28) C(29) 1.374(5) . . yes C(29) C(30) 1.373(5) . . yes C(30) C(31) 1.389(4) . . yes C(32) C(33) 1.361(5) . . yes C(32) C(37) 1.393(5) . . yes C(33) C(34) 1.392(6) . . yes C(34) C(35) 1.324(8) . . yes C(35) C(36) 1.391(8) . . yes C(36) C(37) 1.390(6) . . yes #------------------------------------------------------------------------------ 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(1) N(1) C(4) 110.7(2) . . . yes C(6) N(2) C(9) 111.0(2) . . . yes C(11) N(3) C(14) 106.6(2) . . . yes C(16) N(4) C(19) 111.2(3) . . . yes O(1) C(1) N(1) 124.7(3) . . . yes O(1) C(1) C(2) 129.5(3) . . . yes N(1) C(1) C(2) 105.8(3) . . . yes C(1) C(2) C(3) 108.7(3) . . . yes C(2) C(3) C(4) 109.2(3) . . . yes N(1) C(4) C(3) 105.6(3) . . . yes N(1) C(4) C(5) 126.8(3) . . . yes C(3) C(4) C(5) 127.3(3) . . . yes C(4) C(5) C(6) 124.4(3) . . . yes C(4) C(5) C(20) 118.4(3) . . . yes C(6) C(5) C(20) 117.2(3) . . . yes N(2) C(6) C(5) 123.4(3) . . . yes N(2) C(6) C(7) 106.3(2) . . . yes C(5) C(6) C(7) 130.3(3) . . . yes C(6) C(7) C(8) 108.4(3) . . . yes C(7) C(8) C(9) 107.7(3) . . . yes N(2) C(9) C(8) 106.6(2) . . . yes N(2) C(9) C(10) 121.6(3) . . . yes C(8) C(9) C(10) 131.8(3) . . . yes C(9) C(10) C(11) 122.9(3) . . . yes C(9) C(10) C(26) 118.8(3) . . . yes C(11) C(10) C(26) 118.3(3) . . . yes N(3) C(11) C(10) 123.1(3) . . . yes N(3) C(11) C(12) 108.9(3) . . . yes C(10) C(11) C(12) 127.6(3) . . . yes C(11) C(12) C(13) 107.2(3) . . . yes C(12) C(13) C(14) 106.5(3) . . . yes N(3) C(14) C(13) 110.7(3) . . . yes N(3) C(14) C(15) 122.0(3) . . . yes C(13) C(14) C(15) 127.4(3) . . . yes C(14) C(15) C(16) 122.0(3) . . . yes C(14) C(15) C(32) 119.4(3) . . . yes C(16) C(15) C(32) 118.6(3) . . . yes N(4) C(16) C(15) 124.6(3) . . . yes N(4) C(16) C(17) 105.6(2) . . . yes C(15) C(16) C(17) 129.8(3) . . . yes C(16) C(17) C(18) 109.3(3) . . . yes C(17) C(18) C(19) 108.1(3) . . . yes O(2) C(19) N(4) 123.9(3) . . . yes O(2) C(19) C(18) 130.2(3) . . . yes N(4) C(19) C(18) 105.8(3) . . . yes C(5) C(20) C(21) 119.8(3) . . . yes C(5) C(20) C(25) 121.7(3) . . . yes C(21) C(20) C(25) 118.5(3) . . . yes C(20) C(21) C(22) 120.9(3) . . . yes C(21) C(22) C(23) 119.8(3) . . . yes C(22) C(23) C(24) 120.0(3) . . . yes C(23) C(24) C(25) 120.5(3) . . . yes C(20) C(25) C(24) 120.3(3) . . . yes C(10) C(26) C(27) 121.3(3) . . . yes C(10) C(26) C(31) 119.7(3) . . . yes C(27) C(26) C(31) 118.9(3) . . . yes C(26) C(27) C(28) 119.8(3) . . . yes C(27) C(28) C(29) 120.6(3) . . . yes C(28) C(29) C(30) 120.2(3) . . . yes C(29) C(30) C(31) 119.6(3) . . . yes C(26) C(31) C(30) 120.9(3) . . . yes C(15) C(32) C(33) 121.9(3) . . . yes C(15) C(32) C(37) 119.8(3) . . . yes C(33) C(32) C(37) 118.2(3) . . . yes C(32) C(33) C(34) 121.1(5) . . . yes C(33) C(34) C(35) 120.7(5) . . . yes C(34) C(35) C(36) 120.5(4) . . . yes C(35) C(36) C(37) 119.1(5) . . . yes C(32) C(37) C(36) 120.4(4) . . . yes #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _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(1) N(1) C(4) -179.1(3) . . . . yes O(1) C(1) C(2) C(3) 178.4(4) . . . . yes O(2) C(19) N(4) C(16) 179.1(3) . . . . yes O(2) C(19) C(18) C(17) 179.5(3) . . . . yes N(1) C(1) C(2) C(3) -1.5(4) . . . . yes N(1) C(4) C(3) C(2) -1.0(4) . . . . yes N(1) C(4) C(5) C(6) 9.9(5) . . . . yes N(1) C(4) C(5) C(20) -170.9(3) . . . . yes N(2) C(6) C(5) C(4) 15.8(5) . . . . yes N(2) C(6) C(5) C(20) -163.3(3) . . . . yes N(2) C(6) C(7) C(8) -2.6(3) . . . . yes N(2) C(9) C(8) C(7) -0.3(3) . . . . yes N(2) C(9) C(10) C(11) 9.6(5) . . . . yes N(2) C(9) C(10) C(26) -168.8(3) . . . . yes N(3) C(11) C(10) C(9) 10.0(5) . . . . yes N(3) C(11) C(10) C(26) -171.6(3) . . . . yes N(3) C(11) C(12) C(13) -2.5(4) . . . . yes N(3) C(14) C(13) C(12) -2.1(4) . . . . yes N(3) C(14) C(15) C(16) 7.4(5) . . . . yes N(3) C(14) C(15) C(32) -170.9(3) . . . . yes N(4) C(16) C(15) C(14) 1.1(5) . . . . yes N(4) C(16) C(15) C(32) 179.4(3) . . . . yes N(4) C(16) C(17) C(18) -2.2(4) . . . . yes N(4) C(19) C(18) C(17) -0.4(4) . . . . yes C(1) N(1) C(4) C(3) 0.0(4) . . . . yes C(1) N(1) C(4) C(5) -174.2(3) . . . . yes C(1) C(2) C(3) C(4) 1.6(4) . . . . yes C(2) C(1) N(1) C(4) 0.9(4) . . . . yes C(2) C(3) C(4) C(5) 173.2(3) . . . . yes C(3) C(4) C(5) C(6) -163.1(3) . . . . yes C(3) C(4) C(5) C(20) 16.0(5) . . . . yes C(4) C(5) C(6) C(7) -164.3(3) . . . . yes C(4) C(5) C(20) C(21) 57.1(4) . . . . yes C(4) C(5) C(20) C(25) -122.3(4) . . . . yes C(5) C(6) N(2) C(9) -177.6(3) . . . . yes C(5) C(6) C(7) C(8) 177.5(3) . . . . yes C(5) C(20) C(21) C(22) -178.2(3) . . . . yes C(5) C(20) C(25) C(24) 179.2(4) . . . . yes C(6) N(2) C(9) C(8) -1.4(3) . . . . yes C(6) N(2) C(9) C(10) 179.6(3) . . . . yes C(6) C(5) C(20) C(21) -123.7(3) . . . . yes C(6) C(5) C(20) C(25) 56.9(4) . . . . yes C(6) C(7) C(8) C(9) 1.8(4) . . . . yes C(7) C(6) N(2) C(9) 2.5(3) . . . . yes C(7) C(6) C(5) C(20) 16.6(5) . . . . yes C(7) C(8) C(9) C(10) 178.5(3) . . . . yes C(8) C(9) C(10) C(11) -169.0(3) . . . . yes C(8) C(9) C(10) C(26) 12.5(5) . . . . yes C(9) C(10) C(11) C(12) -162.9(3) . . . . yes C(9) C(10) C(26) C(27) 55.9(4) . . . . yes C(9) C(10) C(26) C(31) -126.9(3) . . . . yes C(10) C(11) N(3) C(14) -172.8(3) . . . . yes C(10) C(11) C(12) C(13) 171.2(3) . . . . yes C(10) C(26) C(27) C(28) 176.7(3) . . . . yes C(10) C(26) C(31) C(30) -176.9(3) . . . . yes C(11) N(3) C(14) C(13) 0.5(4) . . . . yes C(11) N(3) C(14) C(15) 179.0(3) . . . . yes C(11) C(10) C(26) C(27) -122.7(3) . . . . yes C(11) C(10) C(26) C(31) 54.6(4) . . . . yes C(11) C(12) C(13) C(14) 2.7(4) . . . . yes C(12) C(11) N(3) C(14) 1.2(4) . . . . yes C(12) C(11) C(10) C(26) 15.6(5) . . . . yes C(12) C(13) C(14) C(15) 179.5(3) . . . . yes C(13) C(14) C(15) C(16) -174.3(3) . . . . yes C(13) C(14) C(15) C(32) 7.3(5) . . . . yes C(14) C(15) C(16) C(17) 179.9(3) . . . . yes C(14) C(15) C(32) C(33) -62.2(5) . . . . yes C(14) C(15) C(32) C(37) 117.4(4) . . . . yes C(15) C(16) N(4) C(19) -179.0(3) . . . . yes C(15) C(16) C(17) C(18) 178.9(3) . . . . yes C(15) C(32) C(33) C(34) -179.2(4) . . . . yes C(15) C(32) C(37) C(36) 179.3(3) . . . . yes C(16) N(4) C(19) C(18) -1.0(4) . . . . yes C(16) C(15) C(32) C(33) 119.4(4) . . . . yes C(16) C(15) C(32) C(37) -61.0(4) . . . . yes C(16) C(17) C(18) C(19) 1.6(4) . . . . yes C(17) C(16) N(4) C(19) 1.9(4) . . . . yes C(17) C(16) C(15) C(32) -1.7(5) . . . . yes C(20) C(21) C(22) C(23) -1.1(6) . . . . yes C(20) C(25) C(24) C(23) -1.0(7) . . . . yes C(21) C(20) C(25) C(24) -0.2(6) . . . . yes C(21) C(22) C(23) C(24) -0.1(7) . . . . yes C(22) C(21) C(20) C(25) 1.2(6) . . . . yes C(22) C(23) C(24) C(25) 1.2(8) . . . . yes C(26) C(27) C(28) C(29) -0.4(5) . . . . yes C(26) C(31) C(30) C(29) 0.8(5) . . . . yes C(27) C(26) C(31) C(30) 0.4(5) . . . . yes C(27) C(28) C(29) C(30) 1.7(5) . . . . yes C(28) C(27) C(26) C(31) -0.6(5) . . . . yes C(28) C(29) C(30) C(31) -1.8(5) . . . . yes C(32) C(33) C(34) C(35) -0.6(8) . . . . yes C(32) C(37) C(36) C(35) 0.4(6) . . . . yes C(33) C(32) C(37) C(36) -1.0(6) . . . . yes C(33) C(34) C(35) C(36) 0.0(9) . . . . yes C(34) C(33) C(32) C(37) 1.1(6) . . . . yes C(34) C(35) C(36) C(37) 0.2(8) . . . . yes C(34) C(35) C(36) C(37) 0.2(8) . . . . 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) C(18) 3.318(4) . 1_455 ? O(1) C(22) 3.319(4) . 3_655 ? O(1) C(30) 3.359(4) . 2_645 ? O(1) C(21) 3.439(4) . 3_655 ? O(2) N(1) 2.807(3) . 1_655 ? O(2) N(2) 2.851(3) . 1_655 ? O(2) N(3) 3.312(4) . 1_655 ? O(2) C(9) 3.349(4) . 1_655 ? O(2) C(11) 3.434(4) . 1_655 ? O(2) C(10) 3.531(4) . 1_655 ? N(3) C(19) 3.401(4) . 1_455 ? N(4) C(12) 3.453(5) . 1_655 ? N(4) C(11) 3.596(4) . 1_655 ? C(7) C(25) 3.580(5) . 1_455 ? C(8) C(28) 3.595(5) . 1_655 ? C(9) C(28) 3.521(5) . 1_655 ? C(11) C(19) 3.480(4) . 1_455 ? C(14) C(18) 3.469(5) . 1_455 ? C(14) C(19) 3.554(5) . 1_455 ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------