# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Tetsuo Okujima' _publ_contact_author_email TETSUO@CHEM.SCI.EHIME-U.AC.JP _publ_section_title ; Soluble precursors of 2,3-naphthalocyanine and phthalocyanine for use in thin film transistors ; loop_ _publ_author_name 'Tetsuo Okujima' 'Taiji Akiyama' 'Shinji Aramaki' 'Atsuko Hirao' 'Noboru Ono' 'Yoshimasa Sakai' 'Hidemitsu Uno' ; H.Yamada ; data___LessPolar _database_code_depnum_ccdc_archive 'CCDC 692987' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C13 H12 N2 O2 ' _chemical_formula_moiety 'C13 H12 N2 O2 ' _chemical_formula_weight 228.25 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7368(14) _cell_length_b 9.5154(15) _cell_length_c 10.4950(15) _cell_angle_alpha 114.705(17) _cell_angle_beta 95.44(2) _cell_angle_gamma 102.56(2) _cell_volume 583.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1327 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.5 #------------------------------------------------------------------------------ _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.784 _exptl_absorpt_correction_T_max 0.995 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury-8' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 14.6199 _diffrn_reflns_number 6098 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.984 #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR97 _computing_structure_refinement SHELXL97 _computing_publication_material 'CrystalStructure 3.8.2' _computing_molecular_graphics ? #============================================================================== _reflns_number_total 2639 _reflns_number_gt 1445 _reflns_threshold_expression >2sigma(I) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1397P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2639 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1284 _refine_ls_R_factor_gt 0.0782 _refine_ls_wR_factor_ref 0.2465 _refine_ls_wR_factor_gt 0.2034 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.273 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.059 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6777(3) 0.3559(2) 0.41162(18) 0.0645(6) Uani 1 1 d . . . O2 O 0.5461(4) 0.1221(2) 0.20717(19) 0.0713(7) Uani 1 1 d . . . N1 N 0.6312(4) 0.3535(4) -0.2136(3) 0.0836(9) Uani 1 1 d . . . N2 N 0.8841(5) 0.7960(4) 0.1585(4) 0.0935(10) Uani 1 1 d . . . C1 C 0.5648(5) 0.1891(3) 0.3584(3) 0.0584(7) Uani 1 1 d . . . C2 C 0.6467(4) 0.4030(3) 0.3006(3) 0.0540(7) Uani 1 1 d . . . H2 H 0.5477 0.4673 0.3169 0.065 Uiso 1 1 calc R . . C3 C 0.8591(4) 0.4977(3) 0.2911(3) 0.0564(7) Uani 1 1 d . . . H3 H 0.9193 0.6012 0.3769 0.068 Uiso 1 1 calc R . . C4 C 0.8127(4) 0.5189(3) 0.1576(3) 0.0535(7) Uani 1 1 d . . . C5 C 0.7396(4) 0.3788(3) 0.0375(3) 0.0535(7) Uani 1 1 d . . . C6 C 0.7199(4) 0.2315(3) 0.0625(3) 0.0587(7) Uani 1 1 d . . . H6 H 0.6745 0.1306 -0.0268 0.070 Uiso 1 1 calc R . . C7 C 0.5621(4) 0.2443(3) 0.1630(3) 0.0570(7) Uani 1 1 d . . . H7 H 0.4258 0.2374 0.1149 0.068 Uiso 1 1 calc R . . C8 C 0.9250(5) 0.2517(4) 0.1492(3) 0.0660(8) Uani 1 1 d . . . H8 H 0.9953 0.1731 0.1221 0.079 Uiso 1 1 calc R . . C9 C 0.9963(5) 0.3898(4) 0.2666(3) 0.0637(8) Uani 1 1 d . . . H9 H 1.1218 0.4175 0.3288 0.076 Uiso 1 1 calc R . . C10 C 0.6938(5) 0.1104(4) 0.4158(4) 0.0712(9) Uani 1 1 d . . . H10A H 0.6271 -0.0035 0.3732 0.107 Uiso 1 1 calc R . . H10B H 0.7080 0.1553 0.5180 0.107 Uiso 1 1 calc R . . H10C H 0.8288 0.1289 0.3932 0.107 Uiso 1 1 calc R . . C11 C 0.3543(5) 0.1739(4) 0.3966(4) 0.0752(9) Uani 1 1 d . . . H11A H 0.2806 0.2300 0.3607 0.113 Uiso 1 1 calc R . . H11B H 0.3706 0.2200 0.4989 0.113 Uiso 1 1 calc R . . H11C H 0.2771 0.0620 0.3544 0.113 Uiso 1 1 calc R . . C12 C 0.8502(5) 0.6734(4) 0.1587(4) 0.0660(8) Uani 1 1 d . . . C13 C 0.6794(4) 0.3664(4) -0.1015(3) 0.0602(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0861(14) 0.0466(11) 0.0429(10) 0.0158(8) 0.0009(9) -0.0007(10) O2 0.1029(16) 0.0444(11) 0.0452(11) 0.0162(9) 0.0023(10) -0.0060(10) N1 0.0805(18) 0.104(2) 0.0647(18) 0.0445(16) 0.0065(14) 0.0127(16) N2 0.116(2) 0.0633(18) 0.115(3) 0.0466(18) 0.047(2) 0.0278(17) C1 0.0703(17) 0.0417(14) 0.0481(15) 0.0159(11) 0.0002(12) 0.0014(13) C2 0.0668(16) 0.0457(14) 0.0452(14) 0.0191(11) 0.0086(12) 0.0118(12) C3 0.0602(16) 0.0446(14) 0.0484(15) 0.0140(12) 0.0008(12) 0.0033(12) C4 0.0559(14) 0.0447(15) 0.0517(15) 0.0186(12) 0.0080(11) 0.0067(12) C5 0.0535(14) 0.0550(16) 0.0501(15) 0.0252(13) 0.0077(12) 0.0102(12) C6 0.0741(18) 0.0423(14) 0.0439(14) 0.0123(11) 0.0030(12) 0.0053(13) C7 0.0630(16) 0.0495(15) 0.0473(15) 0.0224(12) -0.0015(12) -0.0010(12) C8 0.0740(19) 0.0598(18) 0.0659(19) 0.0282(15) 0.0135(15) 0.0235(15) C9 0.0625(16) 0.0601(18) 0.0617(18) 0.0274(15) 0.0004(13) 0.0097(14) C10 0.083(2) 0.0649(19) 0.0700(19) 0.0349(16) 0.0151(16) 0.0202(16) C11 0.0737(19) 0.074(2) 0.078(2) 0.0389(18) 0.0105(16) 0.0126(16) C12 0.0669(18) 0.0557(18) 0.076(2) 0.0286(16) 0.0234(15) 0.0169(15) C13 0.0532(15) 0.0693(19) 0.0547(17) 0.0307(14) 0.0058(13) 0.0076(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.426(3) . ? O1 C1 1.436(3) . ? O2 C7 1.409(3) . ? O2 C1 1.422(3) . ? N1 C13 1.138(3) . ? N2 C12 1.140(4) . ? C1 C10 1.496(5) . ? C1 C11 1.503(4) . ? C2 C7 1.529(4) . ? C2 C3 1.553(4) . ? C2 H2 0.9800 . ? C3 C9 1.487(4) . ? C3 C4 1.510(4) . ? C3 H3 0.9800 . ? C4 C5 1.342(4) . ? C4 C12 1.432(4) . ? C5 C13 1.424(4) . ? C5 C6 1.512(4) . ? C6 C8 1.508(4) . ? C6 C7 1.555(4) . ? C6 H6 0.9800 . ? C7 H7 0.9800 . ? C8 C9 1.318(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C1 108.89(19) . . ? C7 O2 C1 110.0(2) . . ? O2 C1 O1 104.8(2) . . ? O2 C1 C10 108.8(3) . . ? O1 C1 C10 108.5(2) . . ? O2 C1 C11 110.9(2) . . ? O1 C1 C11 110.5(3) . . ? C10 C1 C11 112.9(2) . . ? O1 C2 C7 104.8(2) . . ? O1 C2 C3 109.5(2) . . ? C7 C2 C3 109.2(2) . . ? O1 C2 H2 111.1 . . ? C7 C2 H2 111.1 . . ? C3 C2 H2 111.1 . . ? C9 C3 C4 108.4(2) . . ? C9 C3 C2 106.5(2) . . ? C4 C3 C2 104.7(2) . . ? C9 C3 H3 112.2 . . ? C4 C3 H3 112.2 . . ? C2 C3 H3 112.2 . . ? C5 C4 C12 123.3(3) . . ? C5 C4 C3 113.5(2) . . ? C12 C4 C3 123.2(2) . . ? C4 C5 C13 124.3(3) . . ? C4 C5 C6 113.7(2) . . ? C13 C5 C6 122.0(2) . . ? C8 C6 C5 107.9(2) . . ? C8 C6 C7 106.3(2) . . ? C5 C6 C7 104.1(2) . . ? C8 C6 H6 112.7 . . ? C5 C6 H6 112.7 . . ? C7 C6 H6 112.7 . . ? O2 C7 C2 105.3(2) . . ? O2 C7 C6 109.8(2) . . ? C2 C7 C6 109.2(2) . . ? O2 C7 H7 110.8 . . ? C2 C7 H7 110.8 . . ? C6 C7 H7 110.8 . . ? C9 C8 C6 114.4(3) . . ? C9 C8 H8 122.8 . . ? C6 C8 H8 122.8 . . ? C8 C9 C3 114.3(3) . . ? C8 C9 H9 122.9 . . ? C3 C9 H9 122.9 . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 C4 178.4(3) . . ? N1 C13 C5 178.7(4) . . ? 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 C7 O2 C1 O1 -23.9(3) . . . . ? C7 O2 C1 C10 -139.8(2) . . . . ? C7 O2 C1 C11 95.4(3) . . . . ? C2 O1 C1 O2 24.9(3) . . . . ? C2 O1 C1 C10 141.0(2) . . . . ? C2 O1 C1 C11 -94.7(3) . . . . ? C1 O1 C2 C7 -16.4(3) . . . . ? C1 O1 C2 C3 -133.4(2) . . . . ? O1 C2 C3 C9 56.9(3) . . . . ? C7 C2 C3 C9 -57.2(3) . . . . ? O1 C2 C3 C4 171.7(2) . . . . ? C7 C2 C3 C4 57.5(3) . . . . ? C9 C3 C4 C5 52.4(3) . . . . ? C2 C3 C4 C5 -61.1(3) . . . . ? C9 C3 C4 C12 -125.5(3) . . . . ? C2 C3 C4 C12 121.0(3) . . . . ? C12 C4 C5 C13 -3.8(4) . . . . ? C3 C4 C5 C13 178.3(2) . . . . ? C12 C4 C5 C6 178.0(2) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C4 C5 C6 C8 -51.4(3) . . . . ? C13 C5 C6 C8 130.2(3) . . . . ? C4 C5 C6 C7 61.2(3) . . . . ? C13 C5 C6 C7 -117.2(3) . . . . ? C1 O2 C7 C2 13.8(3) . . . . ? C1 O2 C7 C6 131.3(2) . . . . ? O1 C2 C7 O2 1.8(3) . . . . ? C3 C2 C7 O2 118.9(2) . . . . ? O1 C2 C7 C6 -116.1(2) . . . . ? C3 C2 C7 C6 1.0(3) . . . . ? C8 C6 C7 O2 -60.0(3) . . . . ? C5 C6 C7 O2 -173.85(19) . . . . ? C8 C6 C7 C2 55.0(3) . . . . ? C5 C6 C7 C2 -58.8(3) . . . . ? C5 C6 C8 C9 51.7(3) . . . . ? C7 C6 C8 C9 -59.5(3) . . . . ? C6 C8 C9 C3 0.6(4) . . . . ? C4 C3 C9 C8 -53.0(3) . . . . ? C2 C3 C9 C8 59.2(3) . . . . ? data___060705Polar _database_code_depnum_ccdc_archive 'CCDC 692988' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C13 H12 N2 O2 ' _chemical_formula_moiety 'C13 H12 N2 O2 ' _chemical_formula_weight 228.25 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/m 1' _symmetry_space_group_name_Hall '-C 2y' _symmetry_Int_Tables_number 12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 13.640(2) _cell_length_b 10.8311(17) _cell_length_c 17.021(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.8340(10) _cell_angle_gamma 90.00 _cell_volume 2365.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3491 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.890 _exptl_absorpt_correction_T_max 0.991 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury-8' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 14.6199 _diffrn_reflns_number 12344 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR97 _computing_structure_refinement SHELXL97 _computing_publication_material 'CrystalStructure 3.8.2' _computing_molecular_graphics ? #============================================================================== _reflns_number_total 2819 _reflns_number_gt 2223 _reflns_threshold_expression >2sigma(I) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0784P)^2^+0.9504P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2819 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1617 _refine_ls_wR_factor_gt 0.1502 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.158 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.042 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.22963(9) 0.39586(11) 0.45777(7) 0.0451(3) Uani 1 1 d . . . O2 O 0.26020(10) 0.39575(11) 1.03346(7) 0.0483(3) Uani 1 1 d . . . N1 N 0.16998(16) 0.30121(19) 0.67665(13) 0.0747(6) Uani 1 1 d . . . N2 N 0.01707(14) 0.30266(18) 0.81849(14) 0.0732(6) Uani 1 1 d . . . C1 C 0.22368(14) 0.36343(18) 0.65554(12) 0.0494(5) Uani 1 1 d . . . C2 C 0.29295(13) 0.43787(15) 0.62882(10) 0.0384(4) Uani 1 1 d . . . C3 C 0.36930(12) 0.38123(16) 0.59256(10) 0.0395(4) Uani 1 1 d . . . H3 H 0.3708 0.2909 0.5960 0.047 Uiso 1 1 calc R . . C4 C 0.33509(12) 0.42882(15) 0.50117(10) 0.0392(4) Uani 1 1 d . . . H4 H 0.3810 0.3966 0.4724 0.047 Uiso 1 1 calc R . . C5 C 0.47505(13) 0.43875(17) 0.63559(11) 0.0460(4) Uani 1 1 d . . . H5 H 0.5350 0.3922 0.6600 0.055 Uiso 1 1 calc R . . C6 C 0.17986(19) 0.5000 0.40846(16) 0.0450(6) Uani 1 2 d S . . C7 C 0.1970(3) 0.5000 0.32550(17) 0.0617(8) Uani 1 2 d S . . H7A H 0.1587 0.4332 0.2918 0.093 Uiso 0.50 1 calc PR . . H7B H 0.2700 0.4899 0.3344 0.093 Uiso 0.50 1 calc PR . . H7C H 0.1734 0.5769 0.2974 0.093 Uiso 0.50 1 calc PR . . C8 C 0.0667(2) 0.5000 0.4009(2) 0.0648(8) Uani 1 2 d S . . H8A H 0.0317 0.4325 0.3661 0.097 Uiso 0.50 1 calc PR . . H8B H 0.0351 0.5764 0.3765 0.097 Uiso 0.50 1 calc PR . . H8C H 0.0611 0.4911 0.4553 0.097 Uiso 0.50 1 calc PR . . C9 C 0.08937(14) 0.36407(18) 0.83766(12) 0.0487(4) Uani 1 1 d . . . C10 C 0.18203(13) 0.43812(15) 0.86250(10) 0.0386(4) Uani 1 1 d . . . C11 C 0.28885(13) 0.38140(16) 0.89987(10) 0.0402(4) Uani 1 1 d . . . H11 H 0.2875 0.2911 0.8963 0.048 Uiso 1 1 calc R . . C12 C 0.33013(13) 0.42876(16) 0.99148(11) 0.0419(4) Uani 1 1 d . . . H12 H 0.4001 0.3965 1.0211 0.050 Uiso 1 1 calc R . . C13 C 0.36037(13) 0.43924(17) 0.85870(11) 0.0452(4) Uani 1 1 d . . . H13 H 0.4009 0.3927 0.8354 0.054 Uiso 1 1 calc R . . C14 C 0.2493(2) 0.5000 1.08106(15) 0.0458(6) Uani 1 2 d S . . C15 C 0.3327(3) 0.5000 1.16604(18) 0.0646(8) Uani 1 2 d S . . H15A H 0.3214 0.5678 1.1983 0.097 Uiso 0.50 1 calc PR . . H15B H 0.3998 0.5084 1.1599 0.097 Uiso 0.50 1 calc PR . . H15C H 0.3301 0.4238 1.1940 0.097 Uiso 0.50 1 calc PR . . C16 C 0.1401(2) 0.5000 1.0842(2) 0.0671(8) Uani 1 2 d S . . H16A H 0.1328 0.5663 1.1193 0.101 Uiso 0.50 1 calc PR . . H16B H 0.1269 0.4228 1.1065 0.101 Uiso 0.50 1 calc PR . . H16C H 0.0910 0.5109 1.0289 0.101 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0439(7) 0.0377(7) 0.0477(7) -0.0012(5) 0.0077(6) -0.0038(5) O2 0.0609(8) 0.0417(7) 0.0490(7) 0.0018(5) 0.0274(6) -0.0020(6) N1 0.0818(13) 0.0646(13) 0.0945(14) -0.0020(10) 0.0520(12) -0.0161(10) N2 0.0569(10) 0.0633(12) 0.1009(15) -0.0055(10) 0.0287(10) -0.0161(9) C1 0.0502(10) 0.0467(10) 0.0542(10) 0.0010(8) 0.0214(9) -0.0033(8) C2 0.0393(8) 0.0376(9) 0.0374(8) 0.0020(6) 0.0117(7) -0.0019(6) C3 0.0405(9) 0.0334(8) 0.0434(9) 0.0003(7) 0.0127(7) 0.0014(6) C4 0.0372(8) 0.0384(9) 0.0428(9) -0.0031(7) 0.0146(7) 0.0008(6) C5 0.0369(9) 0.0470(10) 0.0489(10) 0.0015(8) 0.0077(8) 0.0056(7) C6 0.0426(13) 0.0432(14) 0.0438(13) 0.000 0.0078(11) 0.000 C7 0.0664(18) 0.069(2) 0.0450(15) 0.000 0.0126(14) 0.000 C8 0.0421(15) 0.073(2) 0.075(2) 0.000 0.0143(14) 0.000 C9 0.0462(10) 0.0454(10) 0.0579(11) -0.0018(8) 0.0221(9) -0.0029(8) C10 0.0394(9) 0.0395(9) 0.0394(8) -0.0028(6) 0.0168(7) -0.0037(6) C11 0.0430(9) 0.0335(8) 0.0455(9) -0.0001(7) 0.0172(7) 0.0028(6) C12 0.0397(9) 0.0425(10) 0.0440(9) 0.0030(7) 0.0148(7) 0.0037(7) C13 0.0389(9) 0.0532(10) 0.0470(9) -0.0022(8) 0.0190(8) 0.0039(7) C14 0.0517(14) 0.0462(14) 0.0438(13) 0.000 0.0218(11) 0.000 C15 0.0673(19) 0.078(2) 0.0440(15) 0.000 0.0130(14) 0.000 C16 0.0605(18) 0.075(2) 0.074(2) 0.000 0.0346(16) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.422(2) . ? O1 C6 1.4321(19) . ? O2 C12 1.418(2) . ? O2 C14 1.4266(19) . ? N1 C1 1.139(2) . ? N2 C9 1.141(2) . ? C1 C2 1.429(2) . ? C2 C2 1.346(3) 6_565 ? C2 C3 1.509(2) . ? C3 C5 1.513(2) . ? C3 C4 1.553(2) . ? C3 H3 0.9800 . ? C4 C4 1.542(3) 6_565 ? C4 H4 0.9800 . ? C5 C5 1.327(4) 6_565 ? C5 H5 0.9300 . ? C6 O1 1.4321(19) 6_565 ? C6 C8 1.505(4) . ? C6 C7 1.508(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.434(2) . ? C10 C10 1.340(3) 6_565 ? C10 C11 1.509(2) . ? C11 C13 1.516(2) . ? C11 C12 1.554(2) . ? C11 H11 0.9800 . ? C12 C12 1.543(3) 6_565 ? C12 H12 0.9800 . ? C13 C13 1.316(4) 6_565 ? C13 H13 0.9300 . ? C14 O2 1.4266(19) 6_565 ? C14 C15 1.507(4) . ? C14 C16 1.508(4) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C6 107.56(13) . . ? C12 O2 C14 107.72(14) . . ? N1 C1 C2 178.1(2) . . ? C2 C2 C1 124.35(10) 6_565 . ? C2 C2 C3 113.98(9) 6_565 . ? C1 C2 C3 121.56(15) . . ? C2 C3 C5 108.16(14) . . ? C2 C3 C4 105.09(13) . . ? C5 C3 C4 105.15(13) . . ? C2 C3 H3 112.6 . . ? C5 C3 H3 112.6 . . ? C4 C3 H3 112.6 . . ? O1 C4 C4 104.54(8) . 6_565 ? O1 C4 C3 110.14(13) . . ? C4 C4 C3 109.39(9) 6_565 . ? O1 C4 H4 110.9 . . ? C4 C4 H4 110.9 6_565 . ? C3 C4 H4 110.9 . . ? C5 C5 C3 114.32(9) 6_565 . ? C5 C5 H5 122.8 6_565 . ? C3 C5 H5 122.8 . . ? O1 C6 O1 103.93(18) 6_565 . ? O1 C6 C8 108.58(16) 6_565 . ? O1 C6 C8 108.58(16) . . ? O1 C6 C7 110.82(15) 6_565 . ? O1 C6 C7 110.82(15) . . ? C8 C6 C7 113.6(2) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 178.4(2) . . ? C10 C10 C9 124.00(10) 6_565 . ? C10 C10 C11 114.03(9) 6_565 . ? C9 C10 C11 121.67(15) . . ? C10 C11 C13 108.51(13) . . ? C10 C11 C12 104.95(13) . . ? C13 C11 C12 104.86(14) . . ? C10 C11 H11 112.6 . . ? C13 C11 H11 112.6 . . ? C12 C11 H11 112.6 . . ? O2 C12 C12 104.60(9) . 6_565 ? O2 C12 C11 110.23(14) . . ? C12 C12 C11 109.27(9) 6_565 . ? O2 C12 H12 110.9 . . ? C12 C12 H12 110.9 6_565 . ? C11 C12 H12 110.9 . . ? C13 C13 C11 114.40(9) 6_565 . ? C13 C13 H13 122.8 6_565 . ? C11 C13 H13 122.8 . . ? O2 C14 O2 104.64(18) 6_565 . ? O2 C14 C15 110.77(15) 6_565 . ? O2 C14 C15 110.77(15) . . ? O2 C14 C16 108.35(16) 6_565 . ? O2 C14 C16 108.35(16) . . ? C15 C14 C16 113.5(2) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 C2 C2 C3 C5 51.67(13) 6_565 . . . ? C1 C2 C3 C5 -131.85(16) . . . . ? C2 C2 C3 C4 -60.25(12) 6_565 . . . ? C1 C2 C3 C4 116.23(17) . . . . ? C6 O1 C4 C4 20.69(14) . . . 6_565 ? C6 O1 C4 C3 138.11(15) . . . . ? C2 C3 C4 O1 -57.13(17) . . . . ? C5 C3 C4 O1 -171.17(13) . . . . ? C2 C3 C4 C4 57.24(12) . . . 6_565 ? C5 C3 C4 C4 -56.80(12) . . . 6_565 ? C2 C3 C5 C5 -51.86(13) . . . 6_565 ? C4 C3 C5 C5 60.01(12) . . . 6_565 ? C4 O1 C6 O1 -33.7(2) . . . 6_565 ? C4 O1 C6 C8 -149.16(17) . . . . ? C4 O1 C6 C7 85.37(19) . . . . ? C10 C10 C11 C13 -51.22(13) 6_565 . . . ? C9 C10 C11 C13 134.82(16) . . . . ? C10 C10 C11 C12 60.46(12) 6_565 . . . ? C9 C10 C11 C12 -113.50(17) . . . . ? C14 O2 C12 C12 -19.64(13) . . . 6_565 ? C14 O2 C12 C11 -136.99(16) . . . . ? C10 C11 C12 O2 57.10(17) . . . . ? C13 C11 C12 O2 171.35(13) . . . . ? C10 C11 C12 C12 -57.33(12) . . . 6_565 ? C13 C11 C12 C12 56.93(12) . . . 6_565 ? C10 C11 C13 C13 51.42(13) . . . 6_565 ? C12 C11 C13 C13 -60.31(12) . . . 6_565 ? C12 O2 C14 O2 32.1(2) . . . 6_565 ? C12 O2 C14 C15 -87.27(19) . . . . ? C12 O2 C14 C16 147.57(18) . . . . ?