#------------------------------------------------------------------------------ #$Date: 2012-03-26 03:00:57 +0300 (Mon, 26 Mar 2012) $ #$Revision: 47765 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/58/1505819.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1505819 loop_ _publ_author_name 'Tokumaru, Kazuyuki' 'Arai, Shigeru' 'Nishida, Atsushi' _publ_section_title ; Stereoselective furan-iminium cation cyclization in the construction of the core structure of manzamine A. ; _journal_issue 1 _journal_name_full 'Organic letters' _journal_page_first 27 _journal_page_last 30 _journal_volume 8 _journal_year 2006 _chemical_formula_moiety 'C25 H32 N2 O7 S ' _chemical_formula_sum 'C25 H32 N2 O7 S' _chemical_formula_weight 504.60 _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 33 _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.972(2) _cell_length_b 12.187(3) _cell_length_c 17.556(3) _cell_measurement_reflns_used 16 _cell_measurement_temperature 298.2 _cell_measurement_theta_max 14.7 _cell_measurement_theta_min 12.0 _cell_volume 2561.5(9) _computing_cell_refinement WinAFC _computing_data_collection WinAFC _computing_data_reduction 'teXsan Ver. 1.11' _computing_publication_material 'teXsan Ver. 1.11' _computing_structure_refinement 'teXsan Ver. 1.10' _computing_structure_solution SIR97 _diffrn_measured_fraction_theta_full 0.9996 _diffrn_measured_fraction_theta_max 0.9996 _diffrn_measurement_device_type 'Rigaku AFC7S' _diffrn_measurement_method \w-2\q _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2722 _diffrn_reflns_theta_full 68.98 _diffrn_reflns_theta_max 68.98 _diffrn_standards_decay_% 1.74 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.518 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_correction_T_min 0.812 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.18 _refine_diff_density_min -0.18 _refine_ls_abs_structure_Flack 0.98(6) _refine_ls_extinction_coef 0.056(2) _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_goodness_of_fit_ref 1.377 _refine_ls_hydrogen_treatment noref _refine_ls_number_parameters 317 _refine_ls_number_reflns 2357 _refine_ls_R_factor_gt 0.0407 _refine_ls_shift/su_max 0.0101 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0514 _reflns_number_gt 2014 _reflns_number_total 2466 _reflns_threshold_expression F^2^>2.0\s(F^2^) _[local]_cod_data_source_file ol052387msi20051003_062429.cif _[local]_cod_data_source_block compound_20 _[local]_cod_cif_authors_sg_H-M 'P n a 21 ' _[local]_cod_chemical_formula_sum_orig 'C25 H32 N2 O7 S ' _cod_original_cell_volume 2561(1) _cod_database_code 1505819 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,1/2+z 1/2-x,1/2+y,1/2+z 1/2+x,1/2-y,z loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag S(1) S 0.83215(7) -0.28216(7) 0.2378 0.0607(2) Uani 1.00 d O(1) O 0.7927(2) 0.2420(2) 0.2343(2) 0.0838(9) Uani 1.00 d O(2) O 0.9788(2) 0.2049(2) 0.0988(2) 0.0572(6) Uani 1.00 d O(3) O 1.0232(3) 0.3008(4) -0.0021(3) 0.138(2) Uani 1.00 d O(4) O 0.7985(2) -0.0798(2) 0.0218(2) 0.0546(6) Uani 1.00 d O(5) O 0.9586(2) -0.1151(2) -0.0435(2) 0.0677(8) Uani 1.00 d O(6) O 0.7999(3) -0.2860(3) 0.1596(2) 0.094(1) Uani 1.00 d O(7) O 0.7488(2) -0.2946(2) 0.2952(2) 0.0751(9) Uani 1.00 d N(1) N 0.8922(2) -0.1644(2) 0.2526(2) 0.0556(7) Uani 1.00 d N(2) N 0.9598(2) -0.0116(2) 0.0633(2) 0.0498(7) Uani 1.00 d C(1) C 0.8936(4) 0.0051(3) 0.3214(2) 0.063(1) Uani 1.00 d C(2) C 0.8961(3) -0.1181(3) 0.3296(3) 0.065(1) Uani 1.00 d C(3) C 0.9897(3) -0.1358(3) 0.2074(3) 0.0553(9) Uani 1.00 d C(4) C 0.9981(3) -0.0108(3) 0.1944(3) 0.0480(7) Uani 1.00 d C(5) C 0.9878(3) 0.0488(3) 0.2713(3) 0.0570(9) Uani 1.00 d C(6) C 0.9752(3) 0.1735(3) 0.2614(3) 0.065(1) Uani 1.00 d C(7) C 0.8750(3) 0.1957(3) 0.2135(2) 0.0584(9) Uani 1.00 d C(8) C 0.8839(3) 0.1485(2) 0.1323(2) 0.0498(8) Uani 1.00 d C(9) C 0.9094(2) 0.0232(2) 0.1350(2) 0.0429(7) Uani 1.00 d C(10) C 1.1078(3) 0.0109(3) 0.1516(3) 0.0574(9) Uani 1.00 d C(11) C 1.0820(3) -0.0140(3) 0.0683(3) 0.0622(9) Uani 1.00 d C(12) C 0.7855(3) 0.1771(3) 0.0804(3) 0.069(1) Uani 1.00 d C(13) C 0.8329(5) 0.2357(7) 0.0168(4) 0.153(3) Uani 1.00 d C(14) C 0.9527(5) 0.2546(5) 0.0334(3) 0.092(1) Uani 1.00 d C(15) C 0.9088(3) -0.0739(3) 0.0087(2) 0.0496(8) Uani 1.00 d C(16) C 0.7245(3) -0.1410(3) -0.0309(2) 0.0615(9) Uani 1.00 d C(17) C 0.6150(4) -0.1339(5) 0.0088(3) 0.092(2) Uani 1.00 d C(18) C 0.7234(4) -0.0827(4) -0.1071(3) 0.083(1) Uani 1.00 d C(19) C 0.7626(4) -0.2587(4) -0.0374(3) 0.079(1) Uani 1.00 d C(20) C 0.9347(3) -0.3850(3) 0.2519(3) 0.0613(9) Uani 1.00 d C(21) C 0.9829(4) -0.3972(3) 0.3219(3) 0.075(1) Uani 1.00 d C(22) C 1.0607(4) -0.4799(4) 0.3332(4) 0.099(2) Uani 1.00 d C(23) C 1.0882(4) -0.5480(4) 0.2754(5) 0.105(2) Uani 1.00 d C(24) C 1.0398(6) -0.5372(5) 0.2058(5) 0.113(2) Uani 1.00 d C(25) C 0.9634(5) -0.4542(4) 0.1927(3) 0.090(2) Uani 1.00 d H(1) H 0.9621 -0.3501 0.3655 0.0909 Uiso 1.00 calc H(2) H 1.0978 -0.4890 0.3827 0.1298 Uiso 1.00 calc H(3) H 1.1432 -0.6067 0.2791 0.1266 Uiso 1.00 calc H(4) H 1.0590 -0.5911 0.1652 0.1416 Uiso 1.00 calc H(5) H 0.9312 -0.4418 0.1429 0.1156 Uiso 1.00 calc H(6) H 0.8216 0.0204 0.2975 0.0695 Uiso 1.00 calc H(7) H 0.8958 0.0391 0.3674 0.0772 Uiso 1.00 calc H(8) H 0.8316 -0.1445 0.3597 0.0771 Uiso 1.00 calc H(9) H 0.9615 -0.1400 0.3518 0.0694 Uiso 1.00 calc H(10) H 1.0570 -0.1629 0.2309 0.0670 Uiso 1.00 calc H(11) H 0.9881 -0.1758 0.1601 0.0650 Uiso 1.00 calc H(12) H 0.9663 0.2102 0.3083 0.0791 Uiso 1.00 calc H(13) H 1.0424 0.2025 0.2364 0.0711 Uiso 1.00 calc H(14) H 1.1347 0.0863 0.1576 0.0614 Uiso 1.00 calc H(15) H 1.1685 -0.0360 0.1692 0.0613 Uiso 1.00 calc H(16) H 1.1119 -0.0846 0.0539 0.0769 Uiso 1.00 calc H(17) H 1.1121 0.0400 0.0347 0.0764 Uiso 1.00 calc H(18) H 0.7496 0.1200 0.0670 0.0893 Uiso 1.00 calc H(19) H 0.7382 0.2252 0.1021 0.0865 Uiso 1.00 calc H(20) H 0.8230 0.1888 -0.0278 0.2053 Uiso 1.00 calc H(21) H 0.8027 0.2969 -0.0017 0.1594 Uiso 1.00 calc H(22) H 1.0515 0.0366 0.2964 0.0594 Uiso 1.00 calc H(23) H 0.8405 -0.0136 0.1436 0.0440 Uiso 1.00 calc H(24) H 0.5896 -0.0562 0.0153 0.1138 Uiso 1.00 calc H(25) H 0.5566 -0.1717 -0.0180 0.1095 Uiso 1.00 calc H(26) H 0.6237 -0.1609 0.0586 0.0911 Uiso 1.00 calc H(27) H 0.7937 -0.0858 -0.1338 0.1171 Uiso 1.00 calc H(28) H 0.6718 -0.1162 -0.1404 0.0916 Uiso 1.00 calc H(29) H 0.6998 -0.0089 -0.1024 0.1022 Uiso 1.00 calc H(30) H 0.7705 -0.2922 0.0110 0.1089 Uiso 1.00 calc H(31) H 0.7092 -0.3013 -0.0695 0.0904 Uiso 1.00 calc H(32) H 0.8361 -0.2576 -0.0606 0.1058 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 S(1) 0.0598(4) 0.0560(4) 0.0665(5) -0.0151(4) -0.0131(5) 0.0076(5) O(1) 0.095(2) 0.075(2) 0.082(2) 0.022(1) 0.015(2) -0.017(2) O(2) 0.067(1) 0.046(1) 0.059(1) -0.008(1) -0.005(1) 0.002(1) O(3) 0.123(3) 0.196(5) 0.094(3) -0.063(3) -0.012(2) 0.073(3) O(4) 0.051(1) 0.067(1) 0.046(1) -0.011(1) 0.001(1) -0.016(1) O(5) 0.069(2) 0.083(2) 0.051(1) -0.003(1) 0.016(1) -0.017(1) O(6) 0.120(3) 0.090(2) 0.073(2) -0.040(2) -0.041(2) 0.012(2) O(7) 0.056(1) 0.078(2) 0.092(2) -0.010(1) 0.003(1) 0.014(2) N(1) 0.059(1) 0.048(1) 0.060(2) -0.006(1) -0.006(1) 0.004(1) N(2) 0.043(1) 0.052(1) 0.055(1) -0.003(1) 0.004(1) -0.010(1) C(1) 0.081(3) 0.063(2) 0.045(2) -0.004(2) -0.004(2) -0.009(2) C(2) 0.075(3) 0.065(2) 0.055(2) -0.008(2) -0.011(2) 0.006(2) C(3) 0.052(2) 0.043(1) 0.071(2) 0.002(1) -0.006(1) 0.001(2) C(4) 0.045(1) 0.042(1) 0.058(2) -0.001(1) -0.009(1) -0.001(1) C(5) 0.060(2) 0.054(2) 0.057(2) -0.005(2) -0.020(1) -0.007(1) C(6) 0.083(2) 0.053(2) 0.059(2) -0.008(2) -0.011(2) -0.014(2) C(7) 0.080(2) 0.039(2) 0.056(2) -0.002(1) -0.002(1) -0.004(1) C(8) 0.054(2) 0.041(1) 0.054(2) 0.003(1) -0.006(1) -0.005(1) C(9) 0.040(1) 0.041(1) 0.048(2) -0.002(1) -0.003(1) -0.005(1) C(10) 0.042(1) 0.055(2) 0.075(2) -0.001(1) -0.007(1) 0.000(2) C(11) 0.046(1) 0.066(2) 0.074(2) -0.008(2) 0.007(2) -0.010(2) C(12) 0.063(2) 0.061(2) 0.083(2) 0.017(2) -0.025(2) -0.012(2) C(13) 0.096(3) 0.259(9) 0.104(4) -0.032(4) -0.028(3) 0.114(5) C(14) 0.099(3) 0.111(4) 0.068(3) -0.009(3) -0.021(2) 0.027(2) C(15) 0.051(1) 0.054(2) 0.044(2) -0.006(1) 0.001(1) -0.002(1) C(16) 0.062(2) 0.071(2) 0.052(2) -0.021(2) -0.009(2) -0.015(2) C(17) 0.063(2) 0.133(4) 0.080(3) -0.030(3) 0.004(2) -0.025(3) C(18) 0.089(3) 0.104(3) 0.056(2) -0.022(3) -0.017(2) 0.005(2) C(19) 0.093(3) 0.067(2) 0.076(3) -0.027(2) -0.003(3) -0.018(2) C(20) 0.066(2) 0.048(2) 0.070(2) -0.013(1) 0.011(2) 0.002(1) C(21) 0.081(3) 0.063(2) 0.081(2) 0.002(2) -0.011(2) 0.000(2) C(22) 0.083(3) 0.069(3) 0.144(5) 0.003(2) -0.024(3) 0.012(3) C(23) 0.068(3) 0.059(2) 0.187(5) -0.003(2) 0.008(3) -0.018(3) C(24) 0.116(5) 0.070(3) 0.154(5) -0.009(2) 0.047(3) -0.040(4) C(25) 0.123(4) 0.065(2) 0.082(3) -0.021(2) 0.029(3) -0.017(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ;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 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O O 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; S S 0.333 0.557 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O(6) S(1) O(7) 119.1(2) yes O(6) S(1) N(1) 107.5(2) yes O(6) S(1) C(20) 107.3(3) yes O(7) S(1) N(1) 106.9(2) yes O(7) S(1) C(20) 108.2(2) yes N(1) S(1) C(20) 107.2(2) yes C(8) O(2) C(14) 112.3(4) yes C(15) O(4) C(16) 120.5(3) yes S(1) N(1) C(2) 120.0(3) yes S(1) N(1) C(3) 118.7(3) yes C(2) N(1) C(3) 112.7(3) yes C(9) N(2) C(11) 111.6(3) yes C(9) N(2) C(15) 125.6(3) yes C(11) N(2) C(15) 118.4(3) yes C(2) C(1) C(5) 112.8(4) yes N(1) C(2) C(1) 107.1(3) yes N(1) C(3) C(4) 111.7(3) yes C(3) C(4) C(5) 109.3(3) yes C(3) C(4) C(9) 108.6(3) yes C(3) C(4) C(10) 107.3(3) yes C(5) C(4) C(9) 114.3(3) yes C(5) C(4) C(10) 114.7(3) yes C(9) C(4) C(10) 102.2(3) yes C(1) C(5) C(4) 113.6(3) yes C(1) C(5) C(6) 109.7(4) yes C(4) C(5) C(6) 112.0(3) yes C(5) C(6) C(7) 108.8(3) yes O(1) C(7) C(6) 125.4(4) yes O(1) C(7) C(8) 121.1(4) yes C(6) C(7) C(8) 113.5(4) yes O(2) C(8) C(7) 104.6(3) yes O(2) C(8) C(9) 108.8(3) yes O(2) C(8) C(12) 104.7(3) yes C(7) C(8) C(9) 110.6(3) yes C(7) C(8) C(12) 114.4(4) yes C(9) C(8) C(12) 113.1(3) yes N(2) C(9) C(4) 102.7(3) yes N(2) C(9) C(8) 109.9(3) yes C(4) C(9) C(8) 114.7(3) yes C(4) C(10) C(11) 105.2(3) yes N(2) C(11) C(10) 104.8(3) yes C(8) C(12) C(13) 105.7(4) yes C(12) C(13) C(14) 107.8(5) yes O(2) C(14) O(3) 119.9(6) yes O(2) C(14) C(13) 109.0(5) yes O(3) C(14) C(13) 131.0(5) yes O(4) C(15) O(5) 126.6(4) yes O(4) C(15) N(2) 110.4(3) yes O(5) C(15) N(2) 123.0(4) yes O(4) C(16) C(17) 101.8(3) yes O(4) C(16) C(18) 108.6(3) yes O(4) C(16) C(19) 110.1(4) yes C(17) C(16) C(18) 112.3(5) yes C(17) C(16) C(19) 111.0(4) yes C(18) C(16) C(19) 112.4(4) yes S(1) C(20) C(21) 119.7(4) yes S(1) C(20) C(25) 120.0(5) yes C(21) C(20) C(25) 120.3(5) yes C(20) C(21) C(22) 119.4(6) yes C(21) C(22) C(23) 120.2(7) yes C(22) C(23) C(24) 120.8(6) yes C(23) C(24) C(25) 120.2(6) yes C(20) C(25) C(24) 119.0(6) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S(1) O(6) 1.428(4) yes S(1) O(7) 1.426(4) yes S(1) N(1) 1.625(3) yes S(1) C(20) 1.772(4) yes O(1) C(7) 1.192(5) yes O(2) C(8) 1.452(5) yes O(2) C(14) 1.335(6) yes O(3) C(14) 1.191(7) yes O(4) C(15) 1.342(4) yes O(4) C(16) 1.483(4) yes O(5) C(15) 1.204(5) yes N(1) C(2) 1.466(6) yes N(1) C(3) 1.454(5) yes N(2) C(9) 1.459(5) yes N(2) C(11) 1.466(5) yes N(2) C(15) 1.367(5) yes C(1) C(2) 1.509(6) yes C(1) C(5) 1.526(6) yes C(3) C(4) 1.544(5) yes C(4) C(5) 1.538(6) yes C(4) C(9) 1.546(5) yes C(4) C(10) 1.537(6) yes C(5) C(6) 1.538(6) yes C(6) C(7) 1.490(6) yes C(7) C(8) 1.541(5) yes C(8) C(9) 1.558(5) yes C(8) C(12) 1.529(6) yes C(10) C(11) 1.525(6) yes C(12) C(13) 1.443(8) yes C(13) C(14) 1.482(8) yes C(16) C(17) 1.487(6) yes C(16) C(18) 1.515(6) yes C(16) C(19) 1.509(7) yes C(20) C(21) 1.367(7) yes C(20) C(25) 1.382(7) yes C(21) C(22) 1.386(7) yes C(22) C(23) 1.35(1) yes C(23) C(24) 1.36(1) yes C(24) C(25) 1.383(9) yes loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 O(1) C(23) 3.478(7) 4_445 O(1) C(18) 3.515(6) 3_655 O(3) C(21) 3.306(7) 2_754 O(3) C(12) 3.469(6) 4_555 O(5) C(1) 3.248(5) 2_754 O(5) C(5) 3.410(5) 2_754 O(5) C(6) 3.587(5) 2_754 O(6) C(10) 3.581(5) 4_445 O(7) C(3) 3.566(5) 4_445 C(18) C(21) 3.573(8) 3_654 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag S(1) N(1) C(2) C(1) -148.7(3) yes S(1) N(1) C(3) C(4) 149.1(3) yes S(1) C(20) C(21) C(22) 178.1(4) yes S(1) C(20) C(25) C(24) -177.0(4) yes O(1) C(7) C(6) C(5) 115.0(5) yes O(1) C(7) C(8) O(2) 120.2(4) yes O(1) C(7) C(8) C(9) -122.8(4) yes O(1) C(7) C(8) C(12) 6.2(6) yes O(2) C(8) C(7) C(6) -62.0(4) yes O(2) C(8) C(9) N(2) -43.6(4) yes O(2) C(8) C(9) C(4) 71.5(4) yes O(2) C(8) C(12) C(13) 6.8(6) yes O(2) C(14) C(13) C(12) 4.2(10) yes O(3) C(14) O(2) C(8) -177.3(6) yes O(3) C(14) C(13) C(12) -178.5(8) yes O(4) C(15) N(2) C(9) 13.0(5) yes O(4) C(15) N(2) C(11) 167.4(4) yes O(5) C(15) O(4) C(16) -0.5(7) yes O(5) C(15) N(2) C(9) -167.8(4) yes O(5) C(15) N(2) C(11) -13.4(6) yes O(6) S(1) N(1) C(2) 156.6(4) yes O(6) S(1) N(1) C(3) -57.9(4) yes O(6) S(1) C(20) C(21) 178.0(4) yes O(6) S(1) C(20) C(25) -3.7(4) yes O(7) S(1) N(1) C(2) 27.6(4) yes O(7) S(1) N(1) C(3) 173.1(3) yes O(7) S(1) C(20) C(21) -52.2(4) yes O(7) S(1) C(20) C(25) 126.0(4) yes N(1) S(1) C(20) C(21) 62.8(4) yes N(1) S(1) C(20) C(25) -119.0(4) yes N(1) C(2) C(1) C(5) -56.4(5) yes N(1) C(3) C(4) C(5) 50.9(4) yes N(1) C(3) C(4) C(9) -74.4(4) yes N(1) C(3) C(4) C(10) 175.9(3) yes N(2) C(9) C(4) C(3) -77.3(4) yes N(2) C(9) C(4) C(5) 160.3(3) yes N(2) C(9) C(4) C(10) 35.9(3) yes N(2) C(9) C(8) C(7) -157.9(3) yes N(2) C(9) C(8) C(12) 72.4(4) yes N(2) C(11) C(10) C(4) 18.0(4) yes N(2) C(15) O(4) C(16) 178.6(3) yes C(1) C(2) N(1) C(3) 63.9(5) yes C(1) C(5) C(4) C(3) -45.1(4) yes C(1) C(5) C(4) C(9) 76.8(4) yes C(1) C(5) C(4) C(10) -165.7(4) yes C(1) C(5) C(6) C(7) -69.2(5) yes C(2) N(1) S(1) C(20) -88.2(4) yes C(2) N(1) C(3) C(4) -63.0(4) yes C(2) C(1) C(5) C(4) 50.0(5) yes C(2) C(1) C(5) C(6) 176.3(4) yes C(3) N(1) S(1) C(20) 57.3(4) yes C(3) C(4) C(5) C(6) -170.2(3) yes C(3) C(4) C(9) C(8) 163.5(3) yes C(3) C(4) C(10) C(11) 80.9(4) yes C(4) C(5) C(6) C(7) 58.0(5) yes C(4) C(9) N(2) C(11) -26.5(4) yes C(4) C(9) N(2) C(15) 129.4(4) yes C(4) C(9) C(8) C(7) -42.8(5) yes C(4) C(9) C(8) C(12) -172.6(4) yes C(5) C(4) C(9) C(8) 41.2(5) yes C(5) C(4) C(10) C(11) -157.5(3) yes C(5) C(6) C(7) C(8) -62.6(5) yes C(6) C(5) C(4) C(9) -48.2(5) yes C(6) C(5) C(4) C(10) 69.2(4) yes C(6) C(7) C(8) C(9) 55.0(5) yes C(6) C(7) C(8) C(12) -176.0(4) yes C(7) C(8) O(2) C(14) -125.1(4) yes C(7) C(8) C(12) C(13) 120.6(6) yes C(8) O(2) C(14) C(13) 0.4(8) yes C(8) C(9) N(2) C(11) 96.0(4) yes C(8) C(9) N(2) C(15) -108.1(4) yes C(8) C(9) C(4) C(10) -83.3(4) yes C(8) C(12) C(13) C(14) -6.7(9) yes C(9) N(2) C(11) C(10) 5.6(4) yes C(9) C(4) C(10) C(11) -33.3(4) yes C(9) C(8) O(2) C(14) 116.7(4) yes C(9) C(8) C(12) C(13) -111.6(6) yes C(10) C(11) N(2) C(15) -152.2(4) yes C(12) C(8) O(2) C(14) -4.5(5) yes C(15) O(4) C(16) C(17) 175.3(4) yes C(15) O(4) C(16) C(18) -66.0(5) yes C(15) O(4) C(16) C(19) 57.5(5) yes C(20) C(21) C(22) C(23) -0.3(9) yes C(20) C(25) C(24) C(23) -2.0(9) yes C(21) C(20) C(25) C(24) 1.2(7) yes C(21) C(22) C(23) C(24) 0(1) yes C(22) C(21) C(20) C(25) -0.1(8) yes C(22) C(23) C(24) C(25) 1(1) yes C(22) C(23) C(24) C(25) 1(1) yes