# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jun-ichi Matsuo' _publ_contact_author_email JIMATSUO@P.KANAZAWA-U.AC.JP _publ_section_title ; Intramolecular formal [4 + 2] cycloaddition of 3-ethoxycyclobutanones and alkenes ; loop_ _publ_author_name 'Junichi Matsuo' 'Takaya Hoshikawa' 'Hiroyuki Ishibashi' 'Shun Sasaki' # Attachment '735720_2nd_revision_.cif' data__matsuo4 _database_code_depnum_ccdc_archive 'CCDC 735720' #TrackingRef '735720_2nd_revision_.cif' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C23 H26 O2 ' _chemical_formula_moiety 'C23 H26 O2 ' _chemical_formula_weight 334.46 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,-z -x,-y,-z 1/2+x,1/2-y,z _cell_length_a 10.286(3) _cell_length_b 16.713(4) _cell_length_c 11.099(3) _cell_angle_alpha 90.000(2) _cell_angle_beta 112.789(2) _cell_angle_gamma 90.000(2) _cell_volume 1759.0(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8294 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 30.5 _cell_measurement_temperature 123.2 #------------------------------------------------------------------------------ _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_crystal_F_000 720.00 #------------------------------------------------------------------------------ # 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 14.46 _diffrn_reflns_number 19979 _diffrn_reflns_av_R_equivalents 0.136 _diffrn_reflns_theta_max 30.52 _diffrn_measured_fraction_theta_max 0.8552 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.8552 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_ambient_temperature 123.2 #------------------------------------------------------------------------------ # REFINEMENT DATA _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^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4596 _reflns_number_gt 2609 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0792 _refine_ls_wR_factor_ref 0.0962 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2609 _refine_ls_number_parameters 226 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00212|Fo|^2^]' _refine_ls_shift/su_max 0.0002 _refine_diff_density_max 0.48 _refine_diff_density_min -0.37 _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 H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; C C 0.003 0.002 ;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 O1 O 0.1624(2) 0.9829(1) 0.8037(2) 0.0239(6) Uani 1.00 d . . . O2 O -0.1699(2) 0.8349(1) 0.4531(2) 0.0218(5) Uani 1.00 d . . . C1 C 0.1216(3) 0.9180(2) 0.7551(3) 0.0158(6) Uani 1.00 d . . . C2 C -0.0260(3) 0.9075(2) 0.6507(3) 0.0199(7) Uani 1.00 d . . . C3 C -0.0309(3) 0.8616(2) 0.5291(3) 0.0188(7) Uani 1.00 d . . . C4 C 0.0646(3) 0.7882(2) 0.5652(3) 0.0180(6) Uani 1.00 d . . . C5 C 0.2136(3) 0.8069(2) 0.6644(3) 0.0157(6) Uani 1.00 d . . . C6 C 0.5223(3) 0.9283(2) 0.6451(3) 0.0207(7) Uani 1.00 d . . . C7 C 0.6463(3) 0.9644(2) 0.7274(3) 0.0227(7) Uani 1.00 d . . . C8 C 0.6769(3) 0.9688(2) 0.8599(3) 0.0212(7) Uani 1.00 d . . . C9 C 0.5846(3) 0.9370(2) 0.9103(3) 0.0176(6) Uani 1.00 d . . . C10 C 0.4586(3) 0.9004(2) 0.8291(3) 0.0158(6) Uani 1.00 d . . . C11 C 0.3629(3) 0.8624(2) 0.8883(3) 0.0161(6) Uani 1.00 d . . . C12 C 0.2127(3) 0.8431(2) 0.7928(3) 0.0148(6) Uani 1.00 d . . . C13 C 0.2885(3) 0.8624(2) 0.6022(3) 0.0173(7) Uani 1.00 d . . . C14 C 0.4264(3) 0.8965(2) 0.6950(3) 0.0165(6) Uani 1.00 d . . . C15 C 0.1471(3) 0.7826(2) 0.8604(3) 0.0172(7) Uani 1.00 d . . . C16 C 0.1385(3) 0.8108(2) 0.9866(3) 0.0169(7) Uani 1.00 d . . . C17 C 0.0232(3) 0.8551(2) 0.9860(3) 0.0216(7) Uani 1.00 d . . . C18 C 0.0134(4) 0.8805(2) 1.1012(3) 0.0255(8) Uani 1.00 d . . . C19 C 0.1202(4) 0.8621(2) 1.2194(3) 0.0240(8) Uani 1.00 d . . . C20 C 0.2350(4) 0.8178(2) 1.2223(3) 0.0288(8) Uani 1.00 d . . . C21 C 0.2437(3) 0.7926(2) 1.1064(3) 0.0238(8) Uani 1.00 d . . . C22 C -0.2657(4) 0.8980(2) 0.3914(4) 0.0364(9) Uani 1.00 d . . . C23 C -0.3936(4) 0.8673(2) 0.2852(4) 0.0387(10) Uani 1.00 d . . . H1 H -0.0811 0.8791 0.6882 0.0239 Uiso 1.00 calc . . . H2 H -0.0655 0.9590 0.6239 0.0239 Uiso 1.00 calc . . . H3 H -0.0007 0.8962 0.4772 0.0226 Uiso 1.00 calc . . . H4 H 0.0236 0.7490 0.6017 0.0215 Uiso 1.00 calc . . . H5 H 0.0713 0.7675 0.4881 0.0215 Uiso 1.00 calc . . . H6 H 0.2647 0.7580 0.6857 0.0188 Uiso 1.00 calc . . . H7 H 0.5018 0.9250 0.5541 0.0249 Uiso 1.00 calc . . . H8 H 0.7100 0.9861 0.6928 0.0272 Uiso 1.00 calc . . . H9 H 0.7615 0.9938 0.9165 0.0254 Uiso 1.00 calc . . . H10 H 0.6071 0.9399 1.0016 0.0211 Uiso 1.00 calc . . . H11 H 0.3565 0.8982 0.9523 0.0193 Uiso 1.00 calc . . . H12 H 0.4056 0.8139 0.9292 0.0193 Uiso 1.00 calc . . . H13 H 0.2271 0.9058 0.5627 0.0208 Uiso 1.00 calc . . . H14 H 0.3063 0.8330 0.5369 0.0208 Uiso 1.00 calc . . . H15 H 0.0541 0.7707 0.8008 0.0207 Uiso 1.00 calc . . . H16 H 0.2026 0.7353 0.8788 0.0207 Uiso 1.00 calc . . . H17 H -0.0502 0.8682 0.9049 0.0259 Uiso 1.00 calc . . . H18 H -0.0662 0.9104 1.0987 0.0306 Uiso 1.00 calc . . . H19 H 0.1148 0.8798 1.2987 0.0289 Uiso 1.00 calc . . . H20 H 0.3080 0.8045 1.3037 0.0346 Uiso 1.00 calc . . . H21 H 0.3231 0.7624 1.1094 0.0285 Uiso 1.00 calc . . . H22 H -0.2204 0.9353 0.3559 0.0437 Uiso 1.00 calc . . . H23 H -0.2922 0.9240 0.4546 0.0437 Uiso 1.00 calc . . . H24 H -0.4394 0.8299 0.3200 0.0464 Uiso 1.00 calc . . . H25 H -0.4558 0.9105 0.2462 0.0464 Uiso 1.00 calc . . . H26 H -0.3680 0.8417 0.2212 0.0464 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 O1 0.028(1) 0.0119(9) 0.030(1) -0.0014(9) 0.0091(10) -0.0054(8) O2 0.0148(10) 0.020(1) 0.023(1) 0.0001(8) -0.0011(8) 0.0011(8) C1 0.019(1) 0.014(1) 0.016(1) 0.000(1) 0.009(1) -0.0009(10) C2 0.017(1) 0.018(1) 0.023(1) 0.002(1) 0.006(1) 0.000(1) C3 0.016(1) 0.018(1) 0.022(1) -0.003(1) 0.006(1) -0.001(1) C4 0.016(1) 0.016(1) 0.018(1) -0.001(1) 0.002(1) -0.006(1) C5 0.015(1) 0.014(1) 0.015(1) 0.000(1) 0.003(1) -0.0020(9) C6 0.022(1) 0.021(1) 0.021(1) 0.001(1) 0.010(1) -0.002(1) C7 0.020(1) 0.019(1) 0.032(2) -0.003(1) 0.013(1) 0.000(1) C8 0.015(1) 0.018(1) 0.028(2) -0.002(1) 0.007(1) -0.002(1) C9 0.017(1) 0.016(1) 0.017(1) 0.000(1) 0.003(1) -0.003(1) C10 0.014(1) 0.012(1) 0.021(1) 0.001(1) 0.006(1) -0.0001(10) C11 0.016(1) 0.016(1) 0.015(1) -0.002(1) 0.004(1) -0.0017(10) C12 0.015(1) 0.012(1) 0.015(1) -0.0021(10) 0.004(1) -0.0010(10) C13 0.015(1) 0.020(1) 0.016(1) -0.001(1) 0.005(1) -0.001(1) C14 0.016(1) 0.015(1) 0.018(1) -0.001(1) 0.005(1) -0.001(1) C15 0.017(1) 0.013(1) 0.021(1) -0.002(1) 0.007(1) 0.000(1) C16 0.019(1) 0.014(1) 0.019(1) -0.004(1) 0.009(1) 0.0007(10) C17 0.019(1) 0.023(1) 0.021(1) 0.002(1) 0.006(1) 0.002(1) C18 0.028(2) 0.024(2) 0.027(2) 0.003(1) 0.013(1) 0.000(1) C19 0.032(2) 0.024(1) 0.018(1) -0.003(1) 0.011(1) 0.000(1) C20 0.028(2) 0.036(2) 0.019(1) -0.001(1) 0.005(1) 0.004(1) C21 0.022(2) 0.027(2) 0.023(2) 0.004(1) 0.009(1) 0.007(1) C22 0.026(2) 0.026(2) 0.044(2) 0.003(1) -0.001(2) 0.008(2) C23 0.027(2) 0.033(2) 0.039(2) 0.007(2) -0.005(2) 0.000(2) #------------------------------------------------------------------------------ _computing_data_collection CRYSTALCLEAR _computing_cell_refinement CRYSTALCLEAR _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SHELXS86 _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 O1 C1 1.211(3) . . yes O2 C3 1.422(3) . . yes O2 C22 1.424(4) . . yes C1 C2 1.521(4) . . yes C1 C12 1.522(4) . . yes C2 C3 1.536(4) . . yes C3 C4 1.525(4) . . yes C4 C5 1.534(4) . . yes C5 C12 1.551(4) . . yes C5 C13 1.532(4) . . yes C6 C7 1.387(4) . . yes C6 C14 1.410(4) . . yes C7 C8 1.382(5) . . yes C8 C9 1.380(4) . . yes C9 C10 1.400(4) . . yes C10 C11 1.518(4) . . yes C10 C14 1.395(4) . . yes C11 C12 1.532(4) . . yes C12 C15 1.560(4) . . yes C13 C14 1.504(4) . . yes C15 C16 1.512(4) . . yes C16 C17 1.396(4) . . yes C16 C21 1.385(4) . . yes C17 C18 1.387(4) . . yes C18 C19 1.381(4) . . yes C19 C20 1.384(5) . . yes C20 C21 1.389(5) . . yes C22 C23 1.477(5) . . 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 C3 O2 C22 113.7(2) . . . yes O1 C1 C2 120.9(3) . . . yes O1 C1 C12 122.9(3) . . . yes C2 C1 C12 116.2(2) . . . yes C1 C2 C3 114.2(2) . . . yes O2 C3 C2 111.2(2) . . . yes O2 C3 C4 107.5(2) . . . yes C2 C3 C4 111.9(2) . . . yes C3 C4 C5 112.8(2) . . . yes C4 C5 C12 112.3(2) . . . yes C4 C5 C13 109.7(2) . . . yes C12 C5 C13 111.1(2) . . . yes C7 C6 C14 120.7(3) . . . yes C6 C7 C8 119.8(3) . . . yes C7 C8 C9 120.1(3) . . . yes C8 C9 C10 121.2(3) . . . yes C9 C10 C11 119.9(3) . . . yes C9 C10 C14 119.0(3) . . . yes C11 C10 C14 121.1(2) . . . yes C10 C11 C12 116.0(2) . . . yes C1 C12 C5 106.9(2) . . . yes C1 C12 C11 111.4(2) . . . yes C1 C12 C15 109.3(2) . . . yes C5 C12 C11 110.8(2) . . . yes C5 C12 C15 110.3(2) . . . yes C11 C12 C15 108.2(2) . . . yes C5 C13 C14 115.2(2) . . . yes C6 C14 C10 119.2(3) . . . yes C6 C14 C13 119.4(3) . . . yes C10 C14 C13 121.3(3) . . . yes C12 C15 C16 115.8(2) . . . yes C15 C16 C17 121.0(3) . . . yes C15 C16 C21 121.1(3) . . . yes C17 C16 C21 117.8(3) . . . yes C16 C17 C18 121.6(3) . . . yes C17 C18 C19 119.5(3) . . . yes C18 C19 C20 120.0(3) . . . yes C19 C20 C21 120.0(3) . . . yes C16 C21 C20 121.1(3) . . . yes O2 C22 C23 111.3(3) . . . 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 O1 C18 3.327(4) . 3_577 ? O1 C22 3.400(5) . 3_576 ? O1 C9 3.499(4) . 3_677 ? O1 C8 3.542(4) . 3_677 ? O2 C20 3.477(4) . 4_464 ? C10 C15 3.565(4) . 4_565 ? C20 C23 3.538(5) . 4_566 ? #------------------------------------------------------------------------------ #===END #------------------------------------------------------------------------------ # Attachment '735721_2nd_revision_.cif' data__matsuo6 _database_code_depnum_ccdc_archive 'CCDC 735721' #TrackingRef '735721_2nd_revision_.cif' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C23 H26 O2 ' _chemical_formula_moiety 'C23 H26 O2 ' _chemical_formula_weight 334.46 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21 ' _symmetry_Int_Tables_number 33 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 _cell_length_a 7.3596(5) _cell_length_b 19.161(1) _cell_length_c 13.049(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1840.1(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8669 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 30.5 _cell_measurement_temperature 123.2 #------------------------------------------------------------------------------ _exptl_crystal_description Prism _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 1.207 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_absorpt_correction_T_min 0.938 _exptl_absorpt_correction_T_max 0.985 _exptl_crystal_F_000 720.00 #------------------------------------------------------------------------------ # 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 14.46 _diffrn_reflns_number 21633 _diffrn_reflns_av_R_equivalents 0.017 _diffrn_reflns_theta_max 30.55 _diffrn_measured_fraction_theta_max 1.5605 _diffrn_reflns_theta_full 30.55 _diffrn_measured_fraction_theta_full 1.5605 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_ambient_temperature 123.2 #------------------------------------------------------------------------------ # REFINEMENT DATA _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^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4588 _reflns_number_gt 4049 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0443 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 4049 _refine_ls_number_parameters 226 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00063|Fo|^2^]' _refine_ls_shift/su_max 0.0006 _refine_diff_density_max 0.14 _refine_diff_density_min -0.10 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack 0.5(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; C C 0.003 0.002 ;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 O1 O 0.6076(1) 0.67207(5) 0.4373(3) 0.0342(3) Uani 1.00 d . . . O2 O 0.0769(1) 0.68053(4) 0.2386(3) 0.0237(2) Uani 1.00 d . . . C1 C 0.4450(2) 0.66051(6) 0.4326(3) 0.0225(3) Uani 1.00 d . . . C2 C 0.3334(2) 0.68863(6) 0.3448(3) 0.0226(3) Uani 1.00 d . . . C3 C 0.1797(2) 0.64116(6) 0.3106(3) 0.0214(3) Uani 1.00 d . . . C4 C 0.0684(2) 0.61571(6) 0.4019(3) 0.0215(3) Uani 1.00 d . . . C5 C 0.1921(2) 0.57554(6) 0.4761(3) 0.0202(3) Uani 1.00 d . . . C6 C -0.0975(2) 0.57035(7) 0.7205(3) 0.0287(3) Uani 1.00 d . . . C7 C -0.1457(2) 0.61322(8) 0.8014(3) 0.0353(4) Uani 1.00 d . . . C8 C -0.0597(2) 0.67730(8) 0.8132(3) 0.0346(4) Uani 1.00 d . . . C9 C 0.0724(2) 0.69773(7) 0.7440(3) 0.0291(3) Uani 1.00 d . . . C10 C 0.1217(2) 0.65469(7) 0.6616(3) 0.0234(3) Uani 1.00 d . . . C11 C 0.2644(2) 0.68016(6) 0.5870(3) 0.0239(3) Uani 1.00 d . . . C12 C 0.3465(2) 0.62182(6) 0.5188(3) 0.0201(3) Uani 1.00 d . . . C13 C 0.0862(2) 0.54115(6) 0.5635(3) 0.0233(3) Uani 1.00 d . . . C14 C 0.0349(2) 0.59029(7) 0.6496(3) 0.0232(3) Uani 1.00 d . . . C15 C 0.4827(2) 0.57941(6) 0.5843(3) 0.0237(3) Uani 1.00 d . . . C16 C 0.5426(2) 0.50969(6) 0.5418(3) 0.0238(3) Uani 1.00 d . . . C17 C 0.6213(2) 0.50242(7) 0.4447(3) 0.0289(3) Uani 1.00 d . . . C18 C 0.6789(2) 0.43786(8) 0.4094(3) 0.0334(3) Uani 1.00 d . . . C19 C 0.6590(2) 0.37894(7) 0.4704(3) 0.0353(3) Uani 1.00 d . . . C20 C 0.5824(2) 0.38497(7) 0.5661(3) 0.0354(4) Uani 1.00 d . . . C21 C 0.5249(2) 0.45003(7) 0.6014(3) 0.0288(3) Uani 1.00 d . . . C22 C -0.0462(2) 0.63980(7) 0.1795(3) 0.0319(3) Uani 1.00 d . . . C23 C -0.1265(2) 0.68563(8) 0.0979(3) 0.0335(4) Uani 1.00 d . . . H1 H 0.4143 0.7024 0.2905 0.0383 Uiso 1.00 calc . . . H2 H 0.2791 0.7317 0.3745 0.0383 Uiso 1.00 calc . . . H3 H 0.2377 0.6033 0.2768 0.0383 Uiso 1.00 calc . . . H4 H 0.0126 0.6490 0.4400 0.0383 Uiso 1.00 calc . . . H5 H -0.0179 0.5811 0.3767 0.0383 Uiso 1.00 calc . . . H6 H 0.2542 0.5412 0.4316 0.0383 Uiso 1.00 calc . . . H7 H -0.1674 0.5239 0.7151 0.0383 Uiso 1.00 calc . . . H8 H -0.2455 0.5953 0.8506 0.0383 Uiso 1.00 calc . . . H9 H -0.0965 0.7130 0.8608 0.0383 Uiso 1.00 calc . . . H10 H 0.1353 0.7433 0.7452 0.0383 Uiso 1.00 calc . . . H11 H 0.3708 0.7018 0.6253 0.0383 Uiso 1.00 calc . . . H12 H 0.2096 0.7134 0.5489 0.0383 Uiso 1.00 calc . . . H13 H 0.1633 0.5067 0.5929 0.0383 Uiso 1.00 calc . . . H14 H -0.0192 0.5176 0.5394 0.0383 Uiso 1.00 calc . . . H15 H 0.5785 0.6101 0.5974 0.0383 Uiso 1.00 calc . . . H16 H 0.4493 0.5688 0.6547 0.0383 Uiso 1.00 calc . . . H17 H 0.6385 0.5420 0.3980 0.0383 Uiso 1.00 calc . . . H18 H 0.7543 0.4327 0.3443 0.0383 Uiso 1.00 calc . . . H19 H 0.7029 0.3321 0.4479 0.0383 Uiso 1.00 calc . . . H20 H 0.5738 0.3419 0.6121 0.0383 Uiso 1.00 calc . . . H21 H 0.4636 0.4525 0.6663 0.0383 Uiso 1.00 calc . . . H22 H 0.0371 0.5998 0.1494 0.0383 Uiso 1.00 calc . . . H23 H -0.1432 0.6190 0.2274 0.0383 Uiso 1.00 calc . . . H24 H -0.1981 0.6619 0.0527 0.0383 Uiso 1.00 calc . . . H25 H -0.2028 0.7263 0.1282 0.0383 Uiso 1.00 calc . . . H26 H -0.0341 0.7079 0.0520 0.0383 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 O1 0.0218(4) 0.0333(5) 0.0476(6) -0.0070(4) -0.0046(4) 0.0117(4) O2 0.0281(4) 0.0195(4) 0.0234(4) -0.0020(3) -0.0069(4) 0.0002(3) C1 0.0223(5) 0.0167(5) 0.0287(6) -0.0016(4) -0.0023(5) -0.0001(4) C2 0.0236(6) 0.0192(6) 0.0250(6) -0.0032(4) -0.0003(4) 0.0021(4) C3 0.0219(5) 0.0178(5) 0.0244(6) 0.0015(4) -0.0027(4) -0.0002(4) C4 0.0206(5) 0.0198(5) 0.0242(6) -0.0001(4) -0.0027(4) 0.0005(4) C5 0.0204(5) 0.0176(5) 0.0225(6) -0.0017(4) -0.0020(4) 0.0006(4) C6 0.0229(6) 0.0344(7) 0.0288(7) 0.0017(5) -0.0029(5) 0.0074(5) C7 0.0311(7) 0.0478(8) 0.0269(7) 0.0079(6) 0.0022(6) 0.0061(6) C8 0.0369(8) 0.0390(7) 0.0279(7) 0.0148(6) -0.0011(6) -0.0007(6) C9 0.0322(7) 0.0270(6) 0.0280(7) 0.0072(5) -0.0062(5) -0.0014(5) C10 0.0235(6) 0.0234(6) 0.0233(6) 0.0039(5) -0.0035(5) 0.0022(4) C11 0.0262(6) 0.0176(5) 0.0279(6) -0.0006(4) -0.0019(5) -0.0013(4) C12 0.0199(5) 0.0171(5) 0.0235(6) -0.0003(4) -0.0030(4) -0.0003(4) C13 0.0241(6) 0.0198(6) 0.0261(6) -0.0026(5) -0.0028(5) 0.0032(5) C14 0.0229(6) 0.0243(6) 0.0225(6) 0.0035(5) -0.0044(4) 0.0040(4) C15 0.0241(6) 0.0210(5) 0.0259(6) -0.0009(4) -0.0067(5) 0.0003(4) C16 0.0167(5) 0.0250(6) 0.0297(6) 0.0011(4) -0.0054(5) 0.0002(5) C17 0.0247(6) 0.0300(6) 0.0318(7) 0.0012(5) 0.0004(5) 0.0031(5) C18 0.0256(6) 0.0370(7) 0.0374(8) 0.0045(5) 0.0010(5) -0.0051(6) C19 0.0325(7) 0.0288(6) 0.0446(8) 0.0074(6) -0.0066(6) -0.0059(5) C20 0.0386(8) 0.0250(6) 0.0426(8) 0.0057(6) -0.0049(6) 0.0046(5) C21 0.0280(6) 0.0274(6) 0.0309(7) 0.0032(5) -0.0024(5) 0.0029(5) C22 0.0369(7) 0.0259(6) 0.0329(7) -0.0076(5) -0.0123(6) 0.0016(5) C23 0.0390(8) 0.0343(7) 0.0272(7) -0.0040(6) -0.0114(6) 0.0015(5) #------------------------------------------------------------------------------ _computing_data_collection CRYSTALCLEAR _computing_cell_refinement CRYSTALCLEAR _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SHELXS86 _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 O1 C1 1.219(2) . . yes O2 C3 1.423(2) . . yes O2 C22 1.423(2) . . yes C1 C2 1.509(2) . . yes C1 C12 1.530(2) . . yes C2 C3 1.518(2) . . yes C3 C4 1.526(2) . . yes C4 C5 1.536(2) . . yes C5 C12 1.546(2) . . yes C5 C13 1.531(2) . . yes C6 C7 1.383(2) . . yes C6 C14 1.398(2) . . yes C7 C8 1.390(2) . . yes C8 C9 1.383(2) . . yes C9 C10 1.403(2) . . yes C10 C11 1.513(2) . . yes C10 C14 1.398(2) . . yes C11 C12 1.552(2) . . yes C12 C15 1.547(2) . . yes C13 C14 1.513(2) . . yes C15 C16 1.512(2) . . yes C16 C17 1.401(2) . . yes C16 C21 1.389(2) . . yes C17 C18 1.386(2) . . yes C18 C19 1.388(2) . . yes C19 C20 1.376(2) . . yes C20 C21 1.395(2) . . yes C22 C23 1.501(2) . . 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 C3 O2 C22 113.96(10) . . . yes O1 C1 C2 120.5(1) . . . yes O1 C1 C12 121.1(1) . . . yes C2 C1 C12 118.3(1) . . . yes C1 C2 C3 114.5(1) . . . yes O2 C3 C2 105.83(10) . . . yes O2 C3 C4 113.54(10) . . . yes C2 C3 C4 111.2(1) . . . yes C3 C4 C5 109.52(10) . . . yes C4 C5 C12 112.07(10) . . . yes C4 C5 C13 112.6(1) . . . yes C12 C5 C13 110.66(10) . . . yes C7 C6 C14 121.5(1) . . . yes C6 C7 C8 119.5(1) . . . yes C7 C8 C9 119.9(1) . . . yes C8 C9 C10 121.0(1) . . . yes C9 C10 C11 118.9(1) . . . yes C9 C10 C14 119.1(1) . . . yes C11 C10 C14 122.0(1) . . . yes C10 C11 C12 114.0(1) . . . yes C1 C12 C5 111.2(1) . . . yes C1 C12 C11 104.93(10) . . . yes C1 C12 C15 110.7(1) . . . yes C5 C12 C11 109.49(10) . . . yes C5 C12 C15 111.96(10) . . . yes C11 C12 C15 108.3(1) . . . yes C5 C13 C14 114.3(1) . . . yes C6 C14 C10 119.0(1) . . . yes C6 C14 C13 119.7(1) . . . yes C10 C14 C13 121.2(1) . . . yes C12 C15 C16 116.8(1) . . . yes C15 C16 C17 122.7(1) . . . yes C15 C16 C21 119.7(1) . . . yes C17 C16 C21 117.6(1) . . . yes C16 C17 C18 121.0(1) . . . yes C17 C18 C19 120.2(1) . . . yes C18 C19 C20 119.7(1) . . . yes C19 C20 C21 120.0(1) . . . yes C16 C21 C20 121.5(1) . . . yes O2 C22 C23 108.3(1) . . . 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 O1 C2 3.368(2) . 4_565 ? O1 C4 3.589(2) . 1_655 ? O2 C2 3.379(2) . 4_465 ? O2 C20 3.595(2) . 2_664 ? C6 C15 3.569(2) . 1_455 ? #------------------------------------------------------------------------------ #===END #------------------------------------------------------------------------------ # Attachment '735722_2nd_revision_.cif' data__matsuo10 _database_code_depnum_ccdc_archive 'CCDC 735722' #TrackingRef '735722_2nd_revision_.cif' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C22 H28 N2 O7 ' _chemical_formula_moiety ? _chemical_formula_weight 432.47 _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 11.2136(2) _cell_length_b 11.4312(3) _cell_length_c 19.1419(7) _cell_angle_alpha 85.877(4) _cell_angle_beta 75.202(4) _cell_angle_gamma 61.344(3) _cell_volume 2078.0(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8018 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 30.5 _cell_measurement_temperature 123.2 #------------------------------------------------------------------------------ _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.040 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_T_max 0.996 _exptl_crystal_F_000 920.00 #------------------------------------------------------------------------------ # 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 14.46 _diffrn_reflns_number 24749 _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_theta_max 30.58 _diffrn_measured_fraction_theta_max 0.7983 _diffrn_reflns_theta_full 30.58 _diffrn_measured_fraction_theta_full 0.7983 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 25 _diffrn_ambient_temperature 123.2 #------------------------------------------------------------------------------ # REFINEMENT DATA _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^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 10170 _reflns_number_gt 7267 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0540 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 7267 _refine_ls_number_parameters 559 _refine_ls_goodness_of_fit_ref 1.250 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00090|Fo|^2^]' _refine_ls_shift/su_max 0.0002 _refine_diff_density_max 0.34 _refine_diff_density_min -0.21 _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 H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 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 O1 O -0.0215(1) -0.1647(1) 0.20966(6) 0.0162(3) Uani 1.00 d . . . O2 O 0.1066(1) -0.0708(1) 0.14524(6) 0.0242(3) Uani 1.00 d . . . O3 O 0.2303(1) -0.1348(1) -0.11898(7) 0.0339(4) Uani 1.00 d . . . O4 O 0.1526(1) -0.2369(1) -0.17096(6) 0.0266(3) Uani 1.00 d . . . O5 O -0.1987(1) -0.3779(1) 0.09326(7) 0.0280(3) Uani 1.00 d . . . O6 O -0.1421(1) -0.4081(1) -0.02382(6) 0.0238(3) Uani 1.00 d . . . O7 O 0.1666(1) -0.1805(1) 0.41600(6) 0.0209(3) Uani 1.00 d . . . O8 O 0.3610(1) 0.3505(1) 0.18326(6) 0.0173(3) Uani 1.00 d . . . O9 O 0.3003(1) 0.5462(1) 0.12869(6) 0.0227(3) Uani 1.00 d . . . O10 O 0.3974(1) 0.5215(1) -0.13440(7) 0.0290(3) Uani 1.00 d . . . O11 O 0.5296(2) 0.3325(1) -0.19690(7) 0.0372(4) Uani 1.00 d . . . O12 O 0.6592(1) -0.0671(1) 0.04546(7) 0.0306(3) Uani 1.00 d . . . O13 O 0.7053(1) -0.0770(1) -0.07155(7) 0.0317(3) Uani 1.00 d . . . O14 O 0.5169(1) 0.3950(1) 0.38831(6) 0.0214(3) Uani 1.00 d . . . N1 N 0.1647(1) -0.1960(1) -0.11745(7) 0.0207(3) Uani 1.00 d . . . N2 N -0.1369(1) -0.3669(1) 0.03243(8) 0.0196(3) Uani 1.00 d . . . N3 N 0.4703(2) 0.3999(1) -0.13965(7) 0.0231(4) Uani 1.00 d . . . N4 N 0.6531(1) -0.0146(1) -0.01278(8) 0.0216(3) Uani 1.00 d . . . C1 C -0.0437(2) -0.0953(1) 0.27711(8) 0.0150(3) Uani 1.00 d . . . C2 C 0.0809(2) -0.1768(1) 0.30971(8) 0.0171(3) Uani 1.00 d . . . C3 C 0.0596(2) -0.1036(2) 0.37924(8) 0.0177(4) Uani 1.00 d . . . C4 C -0.0783(2) -0.0778(2) 0.43144(8) 0.0194(4) Uani 1.00 d . . . C5 C -0.2060(2) -0.0033(1) 0.39970(8) 0.0168(3) Uani 1.00 d . . . C6 C -0.3316(2) -0.0133(2) 0.44977(9) 0.0205(4) Uani 1.00 d . . . C7 C -0.3188(2) -0.1440(2) 0.42373(9) 0.0233(4) Uani 1.00 d . . . C8 C -0.2101(2) -0.1899(1) 0.34898(8) 0.0163(3) Uani 1.00 d . . . C9 C -0.2565(2) -0.2422(2) 0.29508(9) 0.0190(4) Uani 1.00 d . . . C10 C -0.3799(2) -0.1329(2) 0.26911(10) 0.0236(4) Uani 1.00 d . . . C11 C -0.3452(2) -0.0232(2) 0.23686(9) 0.0199(4) Uani 1.00 d . . . C12 C -0.3058(2) 0.0343(1) 0.29159(8) 0.0177(3) Uani 1.00 d . . . C13 C -0.1880(2) -0.0670(1) 0.32603(8) 0.0147(3) Uani 1.00 d . . . C14 C 0.0484(2) -0.1373(1) 0.14881(8) 0.0166(3) Uani 1.00 d . . . C15 C 0.0408(2) -0.1948(1) 0.08334(8) 0.0156(3) Uani 1.00 d . . . C16 C 0.1080(2) -0.1738(1) 0.01534(8) 0.0171(3) Uani 1.00 d . . . C17 C 0.0946(2) -0.2193(1) -0.04575(8) 0.0174(3) Uani 1.00 d . . . C18 C 0.0155(2) -0.2837(1) -0.04259(8) 0.0176(4) Uani 1.00 d . . . C19 C -0.0494(2) -0.3016(1) 0.02596(8) 0.0167(3) Uani 1.00 d . . . C20 C -0.0381(2) -0.2606(1) 0.08885(8) 0.0170(3) Uani 1.00 d . . . C21 C 0.2980(2) -0.1835(2) 0.38534(9) 0.0221(4) Uani 1.00 d . . . C22 C 0.3932(2) -0.2607(2) 0.43383(10) 0.0242(4) Uani 1.00 d . . . C23 C 0.3103(2) 0.4165(1) 0.25601(8) 0.0155(3) Uani 1.00 d . . . C24 C 0.4402(2) 0.3749(1) 0.28274(8) 0.0168(3) Uani 1.00 d . . . C25 C 0.3998(2) 0.4394(1) 0.35765(8) 0.0174(4) Uani 1.00 d . . . C26 C 0.2962(2) 0.4033(2) 0.40898(8) 0.0183(4) Uani 1.00 d . . . C27 C 0.1653(2) 0.4376(1) 0.38251(8) 0.0165(3) Uani 1.00 d . . . C28 C 0.0867(2) 0.3674(2) 0.42794(9) 0.0208(4) Uani 1.00 d . . . C29 C 0.1574(2) 0.2276(2) 0.38937(9) 0.0234(4) Uani 1.00 d . . . C30 C 0.2477(2) 0.2315(1) 0.31379(8) 0.0168(3) Uani 1.00 d . . . C31 C 0.2376(2) 0.1575(2) 0.25354(9) 0.0203(4) Uani 1.00 d . . . C32 C 0.0946(2) 0.2298(2) 0.23625(9) 0.0251(4) Uani 1.00 d . . . C33 C 0.0604(2) 0.3715(2) 0.21591(9) 0.0243(4) Uani 1.00 d . . . C34 C 0.0644(2) 0.4503(2) 0.27617(9) 0.0200(4) Uani 1.00 d . . . C35 C 0.2003(1) 0.3822(1) 0.30359(8) 0.0149(3) Uani 1.00 d . . . C36 C 0.3568(2) 0.4257(1) 0.12642(8) 0.0154(3) Uani 1.00 d . . . C37 C 0.4319(2) 0.3415(1) 0.05711(8) 0.0155(3) Uani 1.00 d . . . C38 C 0.4202(2) 0.4062(2) -0.00728(8) 0.0171(4) Uani 1.00 d . . . C39 C 0.4872(2) 0.3306(2) -0.07210(8) 0.0186(4) Uani 1.00 d . . . C40 C 0.5659(2) 0.1927(2) -0.07654(8) 0.0192(4) Uani 1.00 d . . . C41 C 0.5744(2) 0.1325(1) -0.01121(9) 0.0182(4) Uani 1.00 d . . . C42 C 0.5095(2) 0.2028(2) 0.05542(8) 0.0170(4) Uani 1.00 d . . . C43 C 0.6258(2) 0.4220(2) 0.34679(9) 0.0247(4) Uani 1.00 d . . . C44 C 0.7175(2) 0.4112(2) 0.3948(1) 0.0299(5) Uani 1.00 d . . . H1 H -0.0570 0.0110 0.2658 0.0270 Uiso 1.00 calc . . . H2 H 0.1011 -0.2767 0.3189 0.0270 Uiso 1.00 calc . . . H3 H 0.1691 -0.1925 0.2739 0.0270 Uiso 1.00 calc . . . H4 H 0.0627 -0.0166 0.3663 0.0270 Uiso 1.00 calc . . . H5 H -0.0893 -0.0288 0.4755 0.0270 Uiso 1.00 calc . . . H6 H -0.0743 -0.1650 0.4469 0.0270 Uiso 1.00 calc . . . H7 H -0.2215 0.0921 0.3966 0.0270 Uiso 1.00 calc . . . H8 H -0.3158 -0.0246 0.5020 0.0270 Uiso 1.00 calc . . . H9 H -0.4173 0.0634 0.4462 0.0270 Uiso 1.00 calc . . . H10 H -0.2823 -0.2185 0.4561 0.0270 Uiso 1.00 calc . . . H11 H -0.4149 -0.1238 0.4192 0.0270 Uiso 1.00 calc . . . H12 H -0.1119 -0.2682 0.3559 0.0270 Uiso 1.00 calc . . . H13 H -0.1856 -0.2812 0.2507 0.0270 Uiso 1.00 calc . . . H14 H -0.2786 -0.3147 0.3180 0.0270 Uiso 1.00 calc . . . H15 H -0.4098 -0.1670 0.2328 0.0270 Uiso 1.00 calc . . . H16 H -0.4687 -0.0902 0.3109 0.0270 Uiso 1.00 calc . . . H17 H -0.4255 0.0467 0.2186 0.0270 Uiso 1.00 calc . . . H18 H -0.2678 -0.0552 0.1930 0.0270 Uiso 1.00 calc . . . H19 H -0.3908 0.0778 0.3308 0.0270 Uiso 1.00 calc . . . H20 H -0.2821 0.1031 0.2681 0.0270 Uiso 1.00 calc . . . H21 H 0.1698 -0.1299 0.0138 0.0270 Uiso 1.00 calc . . . H22 H -0.0008 -0.3102 -0.0861 0.0270 Uiso 1.00 calc . . . H23 H -0.0869 -0.2775 0.1367 0.0270 Uiso 1.00 calc . . . H24 H 0.2792 -0.0866 0.3839 0.0270 Uiso 1.00 calc . . . H25 H 0.3365 -0.2251 0.3358 0.0270 Uiso 1.00 calc . . . H26 H 0.3580 -0.2170 0.4807 0.0270 Uiso 1.00 calc . . . H27 H 0.4134 -0.3557 0.4363 0.0270 Uiso 1.00 calc . . . H28 H 0.4793 -0.2590 0.4164 0.0270 Uiso 1.00 calc . . . H29 H 0.2725 0.5090 0.2486 0.0270 Uiso 1.00 calc . . . H30 H 0.4914 0.2743 0.2843 0.0270 Uiso 1.00 calc . . . H31 H 0.4984 0.4070 0.2462 0.0270 Uiso 1.00 calc . . . H32 H 0.3600 0.5357 0.3534 0.0270 Uiso 1.00 calc . . . H33 H 0.2691 0.4460 0.4572 0.0270 Uiso 1.00 calc . . . H34 H 0.3507 0.3011 0.4142 0.0270 Uiso 1.00 calc . . . H35 H 0.1098 0.5361 0.3853 0.0270 Uiso 1.00 calc . . . H36 H 0.0931 0.3665 0.4799 0.0270 Uiso 1.00 calc . . . H37 H -0.0113 0.4114 0.4238 0.0270 Uiso 1.00 calc . . . H38 H 0.0906 0.2042 0.3826 0.0270 Uiso 1.00 calc . . . H39 H 0.2172 0.1615 0.4194 0.0270 Uiso 1.00 calc . . . H40 H 0.3429 0.1893 0.3180 0.0270 Uiso 1.00 calc . . . H41 H 0.2708 0.0611 0.2649 0.0270 Uiso 1.00 calc . . . H42 H 0.3101 0.1428 0.2087 0.0270 Uiso 1.00 calc . . . H43 H 0.0847 0.1851 0.1974 0.0270 Uiso 1.00 calc . . . H44 H 0.0216 0.2306 0.2769 0.0270 Uiso 1.00 calc . . . H45 H -0.0281 0.4182 0.2045 0.0270 Uiso 1.00 calc . . . H46 H 0.1318 0.3643 0.1703 0.0270 Uiso 1.00 calc . . . H47 H -0.0191 0.4735 0.3184 0.0270 Uiso 1.00 calc . . . H48 H 0.0347 0.5488 0.2656 0.0270 Uiso 1.00 calc . . . H49 H 0.3633 0.5049 -0.0040 0.0270 Uiso 1.00 calc . . . H50 H 0.6146 0.1398 -0.1207 0.0270 Uiso 1.00 calc . . . H51 H 0.5203 0.1560 0.0978 0.0270 Uiso 1.00 calc . . . H52 H 0.5850 0.5118 0.3270 0.0270 Uiso 1.00 calc . . . H53 H 0.6767 0.3671 0.3053 0.0270 Uiso 1.00 calc . . . H54 H 0.7559 0.3255 0.4152 0.0270 Uiso 1.00 calc . . . H55 H 0.6682 0.4755 0.4380 0.0270 Uiso 1.00 calc . . . H56 H 0.7977 0.4168 0.3683 0.0270 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 O1 0.0175(5) 0.0190(5) 0.0123(5) -0.0101(4) -0.0007(4) -0.0015(4) O2 0.0286(6) 0.0355(7) 0.0168(6) -0.0236(5) -0.0008(5) -0.0020(5) O3 0.0449(8) 0.0547(8) 0.0208(6) -0.0397(7) -0.0064(6) 0.0072(6) O4 0.0299(6) 0.0384(7) 0.0141(6) -0.0183(6) -0.0051(5) 0.0001(5) O5 0.0303(6) 0.0385(7) 0.0241(6) -0.0249(6) -0.0044(5) 0.0050(5) O6 0.0250(6) 0.0256(6) 0.0258(6) -0.0139(5) -0.0095(5) -0.0017(5) O7 0.0181(5) 0.0274(6) 0.0197(6) -0.0122(5) -0.0064(4) 0.0033(5) O8 0.0226(5) 0.0159(5) 0.0103(5) -0.0080(4) -0.0016(4) 0.0004(4) O9 0.0280(6) 0.0177(5) 0.0178(6) -0.0075(5) -0.0054(5) 0.0024(4) O10 0.0308(7) 0.0298(7) 0.0226(6) -0.0129(5) -0.0055(5) 0.0099(5) O11 0.0539(9) 0.0420(8) 0.0126(6) -0.0229(7) -0.0027(6) -0.0005(5) O12 0.0334(7) 0.0222(6) 0.0279(7) -0.0065(5) -0.0087(6) 0.0025(5) O13 0.0344(7) 0.0253(6) 0.0283(7) -0.0112(5) 0.0005(6) -0.0088(5) O14 0.0194(5) 0.0292(6) 0.0212(6) -0.0149(5) -0.0076(5) 0.0034(5) N1 0.0211(6) 0.0271(7) 0.0159(7) -0.0135(6) -0.0041(5) 0.0032(5) N2 0.0178(6) 0.0195(6) 0.0235(7) -0.0099(5) -0.0058(5) 0.0017(5) N3 0.0266(7) 0.0313(8) 0.0143(7) -0.0170(6) -0.0041(6) 0.0042(6) N4 0.0169(6) 0.0213(7) 0.0255(7) -0.0090(5) -0.0023(6) -0.0028(6) C1 0.0163(7) 0.0159(7) 0.0115(7) -0.0071(6) -0.0016(5) -0.0023(5) C2 0.0147(7) 0.0204(7) 0.0146(7) -0.0077(6) -0.0017(6) -0.0007(6) C3 0.0175(7) 0.0203(7) 0.0160(7) -0.0092(6) -0.0051(6) 0.0017(6) C4 0.0195(7) 0.0238(8) 0.0139(7) -0.0099(6) -0.0025(6) -0.0015(6) C5 0.0166(7) 0.0160(7) 0.0151(7) -0.0066(6) -0.0012(6) -0.0016(6) C6 0.0185(7) 0.0228(8) 0.0154(7) -0.0070(6) -0.0022(6) 0.0000(6) C7 0.0239(8) 0.0272(8) 0.0185(8) -0.0148(7) 0.0012(6) 0.0001(7) C8 0.0165(7) 0.0153(7) 0.0154(7) -0.0070(6) -0.0024(6) 0.0012(5) C9 0.0190(7) 0.0187(7) 0.0199(8) -0.0100(6) -0.0031(6) 0.0004(6) C10 0.0205(8) 0.0270(8) 0.0273(9) -0.0128(7) -0.0096(7) 0.0035(7) C11 0.0166(7) 0.0235(8) 0.0183(8) -0.0077(6) -0.0067(6) 0.0035(6) C12 0.0177(7) 0.0155(7) 0.0153(7) -0.0049(6) -0.0031(6) 0.0016(6) C13 0.0146(6) 0.0142(6) 0.0134(7) -0.0064(5) -0.0011(5) 0.0000(5) C14 0.0153(7) 0.0192(7) 0.0152(7) -0.0085(6) -0.0026(6) -0.0001(6) C15 0.0142(6) 0.0175(7) 0.0142(7) -0.0067(6) -0.0036(6) 0.0000(6) C16 0.0163(7) 0.0184(7) 0.0172(7) -0.0091(6) -0.0033(6) 0.0015(6) C17 0.0161(7) 0.0194(7) 0.0146(7) -0.0080(6) -0.0018(6) 0.0018(6) C18 0.0174(7) 0.0175(7) 0.0166(7) -0.0065(6) -0.0054(6) -0.0003(6) C19 0.0156(7) 0.0165(7) 0.0191(7) -0.0083(6) -0.0045(6) 0.0003(6) C20 0.0154(7) 0.0184(7) 0.0160(7) -0.0076(6) -0.0025(6) 0.0005(6) C21 0.0198(8) 0.0255(8) 0.0233(8) -0.0128(6) -0.0038(6) -0.0013(6) C22 0.0212(8) 0.0245(8) 0.0287(9) -0.0105(7) -0.0080(7) -0.0038(7) C23 0.0188(7) 0.0138(6) 0.0108(7) -0.0060(6) -0.0019(5) -0.0012(5) C24 0.0165(7) 0.0179(7) 0.0153(7) -0.0084(6) -0.0026(6) 0.0011(6) C25 0.0178(7) 0.0191(7) 0.0171(7) -0.0094(6) -0.0057(6) 0.0006(6) C26 0.0185(7) 0.0243(8) 0.0134(7) -0.0114(6) -0.0027(6) -0.0013(6) C27 0.0175(7) 0.0170(7) 0.0135(7) -0.0074(6) -0.0025(6) -0.0012(6) C28 0.0210(7) 0.0282(8) 0.0152(7) -0.0148(7) -0.0011(6) -0.0003(6) C29 0.0314(9) 0.0254(8) 0.0175(8) -0.0177(7) -0.0041(7) 0.0017(6) C30 0.0172(7) 0.0163(7) 0.0168(7) -0.0076(6) -0.0047(6) 0.0013(6) C31 0.0220(8) 0.0179(7) 0.0201(8) -0.0093(6) -0.0033(6) -0.0028(6) C32 0.0235(8) 0.0317(9) 0.0243(9) -0.0152(7) -0.0066(7) -0.0054(7) C33 0.0207(8) 0.0305(9) 0.0212(8) -0.0090(7) -0.0102(6) -0.0012(7) C34 0.0161(7) 0.0201(7) 0.0198(8) -0.0040(6) -0.0064(6) -0.0015(6) C35 0.0152(7) 0.0149(7) 0.0129(7) -0.0054(5) -0.0040(5) -0.0001(5) C36 0.0141(6) 0.0181(7) 0.0156(7) -0.0084(6) -0.0053(6) 0.0033(6) C37 0.0141(7) 0.0188(7) 0.0145(7) -0.0088(6) -0.0029(5) 0.0014(6) C38 0.0168(7) 0.0203(7) 0.0158(7) -0.0103(6) -0.0036(6) 0.0020(6) C39 0.0207(7) 0.0248(8) 0.0142(7) -0.0140(6) -0.0047(6) 0.0040(6) C40 0.0178(7) 0.0262(8) 0.0152(7) -0.0123(6) -0.0020(6) -0.0021(6) C41 0.0150(7) 0.0190(7) 0.0217(8) -0.0088(6) -0.0038(6) -0.0013(6) C42 0.0155(7) 0.0208(7) 0.0173(7) -0.0103(6) -0.0054(6) 0.0030(6) C43 0.0207(8) 0.0322(9) 0.0236(8) -0.0155(7) -0.0021(6) -0.0018(7) C44 0.0223(8) 0.0356(10) 0.037(1) -0.0166(7) -0.0099(8) 0.0028(8) #------------------------------------------------------------------------------ _computing_data_collection CRYSTALCLEAR _computing_cell_refinement CRYSTALCLEAR _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _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 O1 C1 1.467(2) . . yes O1 C14 1.337(2) . . yes O2 C14 1.205(2) . . yes O3 N1 1.229(2) . . yes O4 N1 1.220(2) . . yes O5 N2 1.226(2) . . yes O6 N2 1.231(2) . . yes O7 C3 1.428(2) . . yes O7 C21 1.424(2) . . yes O8 C23 1.472(2) . . yes O8 C36 1.333(2) . . yes O9 C36 1.207(2) . . yes O10 N3 1.224(2) . . yes O11 N3 1.222(2) . . yes O12 N4 1.230(2) . . yes O13 N4 1.223(2) . . yes O14 C25 1.427(2) . . yes O14 C43 1.431(2) . . yes N1 C17 1.473(2) . . yes N2 C19 1.470(2) . . yes N3 C39 1.473(2) . . yes N4 C41 1.476(2) . . yes C1 C2 1.524(2) . . yes C1 C13 1.539(2) . . yes C2 C3 1.528(2) . . yes C3 C4 1.514(2) . . yes C4 C5 1.532(2) . . yes C5 C6 1.538(2) . . yes C5 C13 1.556(2) . . yes C6 C7 1.538(2) . . yes C7 C8 1.553(2) . . yes C8 C9 1.534(2) . . yes C8 C13 1.556(2) . . yes C9 C10 1.525(2) . . yes C10 C11 1.530(2) . . yes C11 C12 1.529(2) . . yes C12 C13 1.546(2) . . yes C14 C15 1.496(2) . . yes C15 C16 1.396(2) . . yes C15 C20 1.391(2) . . yes C16 C17 1.384(2) . . yes C17 C18 1.387(2) . . yes C18 C19 1.382(2) . . yes C19 C20 1.379(2) . . yes C21 C22 1.505(2) . . yes C23 C24 1.514(2) . . yes C23 C35 1.530(2) . . yes C24 C25 1.518(2) . . yes C25 C26 1.518(2) . . yes C26 C27 1.538(2) . . yes C27 C28 1.537(2) . . yes C27 C35 1.560(2) . . yes C28 C29 1.544(2) . . yes C29 C30 1.551(2) . . yes C30 C31 1.535(2) . . yes C30 C35 1.554(2) . . yes C31 C32 1.526(2) . . yes C32 C33 1.521(3) . . yes C33 C34 1.535(2) . . yes C34 C35 1.554(2) . . yes C36 C37 1.494(2) . . yes C37 C38 1.394(2) . . yes C37 C42 1.394(2) . . yes C38 C39 1.381(2) . . yes C39 C40 1.384(2) . . yes C40 C41 1.386(2) . . yes C41 C42 1.383(2) . . yes C43 C44 1.504(3) . . 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 C1 O1 C14 117.1(1) . . . yes C3 O7 C21 115.2(1) . . . yes C23 O8 C36 118.1(1) . . . yes C25 O14 C43 114.2(1) . . . yes O3 N1 O4 124.5(1) . . . yes O3 N1 C17 117.3(1) . . . yes O4 N1 C17 118.2(1) . . . yes O5 N2 O6 124.3(1) . . . yes O5 N2 C19 118.1(1) . . . yes O6 N2 C19 117.6(1) . . . yes O10 N3 O11 124.5(1) . . . yes O10 N3 C39 117.4(1) . . . yes O11 N3 C39 118.0(1) . . . yes O12 N4 O13 123.9(1) . . . yes O12 N4 C41 117.7(1) . . . yes O13 N4 C41 118.3(1) . . . yes O1 C1 C2 109.1(1) . . . yes O1 C1 C13 108.2(1) . . . yes C2 C1 C13 115.5(1) . . . yes C1 C2 C3 109.3(1) . . . yes O7 C3 C2 112.1(1) . . . yes O7 C3 C4 106.4(1) . . . yes C2 C3 C4 110.0(1) . . . yes C3 C4 C5 114.1(1) . . . yes C4 C5 C6 109.1(1) . . . yes C4 C5 C13 113.7(1) . . . yes C6 C5 C13 103.4(1) . . . yes C5 C6 C7 104.9(1) . . . yes C6 C7 C8 107.8(1) . . . yes C7 C8 C9 112.4(1) . . . yes C7 C8 C13 104.3(1) . . . yes C9 C8 C13 115.6(1) . . . yes C8 C9 C10 113.5(1) . . . yes C9 C10 C11 110.1(1) . . . yes C10 C11 C12 111.0(1) . . . yes C11 C12 C13 116.5(1) . . . yes C1 C13 C5 107.9(1) . . . yes C1 C13 C8 116.9(1) . . . yes C1 C13 C12 109.9(1) . . . yes C5 C13 C8 102.8(1) . . . yes C5 C13 C12 108.2(1) . . . yes C8 C13 C12 110.4(1) . . . yes O1 C14 O2 125.7(1) . . . yes O1 C14 C15 111.3(1) . . . yes O2 C14 C15 122.9(1) . . . yes C14 C15 C16 118.2(1) . . . yes C14 C15 C20 121.6(1) . . . yes C16 C15 C20 120.1(1) . . . yes C15 C16 C17 118.8(1) . . . yes N1 C17 C16 118.7(1) . . . yes N1 C17 C18 118.4(1) . . . yes C16 C17 C18 122.9(1) . . . yes C17 C18 C19 116.0(1) . . . yes N2 C19 C18 118.3(1) . . . yes N2 C19 C20 117.9(1) . . . yes C18 C19 C20 123.8(1) . . . yes C15 C20 C19 118.4(1) . . . yes O7 C21 C22 107.4(1) . . . yes O8 C23 C24 105.8(1) . . . yes O8 C23 C35 110.1(1) . . . yes C24 C23 C35 115.7(1) . . . yes C23 C24 C25 110.2(1) . . . yes O14 C25 C24 112.8(1) . . . yes O14 C25 C26 106.5(1) . . . yes C24 C25 C26 109.8(1) . . . yes C25 C26 C27 113.8(1) . . . yes C26 C27 C28 109.2(1) . . . yes C26 C27 C35 113.5(1) . . . yes C28 C27 C35 103.5(1) . . . yes C27 C28 C29 104.6(1) . . . yes C28 C29 C30 107.5(1) . . . yes C29 C30 C31 113.0(1) . . . yes C29 C30 C35 104.7(1) . . . yes C31 C30 C35 115.3(1) . . . yes C30 C31 C32 112.7(1) . . . yes C31 C32 C33 110.5(1) . . . yes C32 C33 C34 111.4(1) . . . yes C33 C34 C35 115.8(1) . . . yes C23 C35 C27 108.1(1) . . . yes C23 C35 C30 116.5(1) . . . yes C23 C35 C34 109.6(1) . . . yes C27 C35 C30 102.2(1) . . . yes C27 C35 C34 108.9(1) . . . yes C30 C35 C34 111.0(1) . . . yes O8 C36 O9 125.9(1) . . . yes O8 C36 C37 111.2(1) . . . yes O9 C36 C37 122.9(1) . . . yes C36 C37 C38 117.6(1) . . . yes C36 C37 C42 122.3(1) . . . yes C38 C37 C42 120.1(1) . . . yes C37 C38 C39 118.8(1) . . . yes N3 C39 C38 118.3(1) . . . yes N3 C39 C40 118.5(1) . . . yes C38 C39 C40 123.2(1) . . . yes C39 C40 C41 116.0(1) . . . yes N4 C41 C40 118.2(1) . . . yes N4 C41 C42 118.3(1) . . . yes C40 C41 C42 123.5(1) . . . yes C37 C42 C41 118.4(1) . . . yes O14 C43 C44 108.2(1) . . . 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 O1 O9 3.576(2) . 1_545 ? O2 C40 3.170(2) . 2_655 ? O2 N1 3.245(2) . 2_555 ? O2 O4 3.282(2) . 2_555 ? O2 O13 3.294(2) . 2_655 ? O2 O3 3.511(2) . 2_555 ? O3 C42 3.179(2) . 2_655 ? O3 C11 3.190(2) . 2_555 ? O3 C14 3.332(2) . 2_555 ? O3 O10 3.444(2) . 1_545 ? O3 C12 3.451(2) . 2_555 ? O3 C15 3.497(2) . 2_555 ? O3 O12 3.598(2) . 2_655 ? O4 O10 3.014(2) . 1_545 ? O4 C32 3.284(2) . 2_555 ? O5 N3 3.073(2) . 2_555 ? O5 C39 3.143(2) . 2_555 ? O5 O10 3.271(2) . 2_555 ? O5 O12 3.293(2) . 1_455 ? O5 O6 3.356(2) . 2_545 ? O5 C38 3.452(2) . 2_555 ? O5 C18 3.468(2) . 2_545 ? O5 O11 3.537(2) . 2_555 ? O6 N2 2.917(2) . 2_545 ? O6 C19 2.960(2) . 2_545 ? O6 C38 3.012(2) . 2_555 ? O6 C37 3.188(2) . 2_555 ? O6 O6 3.193(2) . 2_545 ? O6 C18 3.395(2) . 2_545 ? O6 C20 3.468(2) . 2_545 ? O6 O13 3.490(2) . 1_455 ? O6 C39 3.528(2) . 2_555 ? O6 C36 3.554(2) . 2_555 ? O6 O12 3.581(2) . 1_455 ? O8 O10 3.559(2) . 2_665 ? O9 N3 2.975(2) . 2_665 ? O9 O10 3.124(2) . 2_665 ? O9 C39 3.243(2) . 2_665 ? O9 C15 3.263(2) . 1_565 ? O9 C14 3.326(2) . 1_565 ? O9 O11 3.366(2) . 2_665 ? O10 N1 2.997(2) . 1_565 ? O10 C36 3.132(2) . 2_665 ? O10 C17 3.364(2) . 1_565 ? O10 C24 3.424(2) . 2_665 ? O12 C19 3.020(2) . 1_655 ? O12 N2 3.058(2) . 1_655 ? O12 C41 3.267(2) . 2_655 ? O12 C20 3.329(2) . 1_655 ? O12 C40 3.372(2) . 2_655 ? O12 N4 3.381(2) . 2_655 ? O12 O13 3.505(2) . 2_655 ? O12 C18 3.550(2) . 1_655 ? O13 C42 3.293(2) . 2_655 ? O13 C18 3.302(2) . 1_655 ? O13 C32 3.383(2) . 2_655 ? O13 C41 3.460(2) . 2_655 ? O13 C31 3.486(2) . 2_655 ? O13 N4 3.570(2) . 2_655 ? O13 C19 3.579(2) . 1_655 ? O14 C22 3.579(2) . 1_565 ? N1 C14 3.500(2) . 2_555 ? N2 N2 3.141(3) . 2_545 ? N2 C19 3.434(2) . 2_545 ? N2 C18 3.557(2) . 2_545 ? N2 C38 3.565(2) . 2_555 ? N3 C36 3.439(2) . 2_665 ? N4 N4 3.195(3) . 2_655 ? N4 C41 3.338(2) . 2_655 ? N4 C19 3.586(2) . 1_655 ? C9 C34 3.582(2) . 1_545 ? C12 C24 3.579(2) . 1_455 ? C22 C43 3.509(2) . 1_545 ? C38 C38 3.449(3) . 2_665 ? #------------------------------------------------------------------------------ #===END #------------------------------------------------------------------------------