Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; Department of Chemistry Nanjing University Nanjing 210093 People's Republic of China ; _publ_contact_author_name 'Prof. Jian-Hua Xu' _publ_section_title ; Aromatic Annulation Strategy for Naphthalenes Fused at 1,2- and 3,4- Positions with Two Heterocycles ; _publ_contact_author_email ' XUJH@NJU.EDU.CN' loop_ _publ_author_name 'Jian-Hua Xu' 'Hui-Ying An' 'Min Zhang' 'Bao-Guo Zhao' data_4a _database_code_depnum_ccdc_archive 'CCDC 280979' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H13 Cl2 N O3' _chemical_formula_sum 'C19 H13 Cl2 N O3' _chemical_formula_weight 374.20 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.895(3) _cell_length_b 9.910(2) _cell_length_c 13.175(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.54(3) _cell_angle_gamma 90.00 _cell_volume 1683.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.404 _exptl_absorpt_correction_type PSI-scan _exptl_absorpt_correction_T_min 0.9325 _exptl_absorpt_correction_T_max 0.9710 _exptl_absorpt_process_details '(XCAD4; Harms & Wocadlo,1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3110 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2971 _reflns_number_gt 2002 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CAD4 Software(Enraf-Nonius,1989)' _computing_cell_refinement 'CAD4 Software' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.1526P)^2^+1.2P] 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 SHELXL _refine_ls_extinction_coef 0.018(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2971 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0926 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.2266 _refine_ls_wR_factor_gt 0.1931 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Cl1 Cl 0.89950(9) 0.12197(12) 0.14174(10) 0.0521(4) Uani 1 1 d . . . Cl2 Cl 0.76664(10) 0.00535(15) -0.05529(9) 0.0637(5) Uani 1 1 d . . . O3 O 0.6168(2) -0.1054(3) 0.0880(2) 0.0425(8) Uani 1 1 d . . . O2 O 1.0112(2) -0.1337(4) 0.2250(3) 0.0574(10) Uani 1 1 d . . . N N 0.9573(3) -0.2280(4) 0.0743(3) 0.0445(9) Uani 1 1 d . . . C3 C 0.8577(3) -0.0469(4) 0.1379(3) 0.0351(9) Uani 1 1 d . . . C13 C 0.7157(3) -0.1646(4) 0.1118(3) 0.0372(10) Uani 1 1 d . . . C4 C 0.8057(3) -0.1048(4) 0.0415(3) 0.0385(10) Uani 1 1 d . . . C15 C 0.6418(4) -0.3767(5) 0.0392(4) 0.0472(11) Uani 1 1 d . . . H15A H 0.6007 -0.3239 -0.0035 0.057 Uiso 1 1 calc R . . C2 C 0.9521(3) -0.1383(4) 0.1542(3) 0.0397(10) Uani 1 1 d . . . O1 O 0.8703(3) -0.2779(4) -0.0737(3) 0.0670(11) Uani 1 1 d . . . C6 C 0.7633(3) -0.0865(4) 0.2037(3) 0.0381(10) Uani 1 1 d . . . H6A H 0.7793 -0.1414 0.2637 0.046 Uiso 1 1 calc R . . C7 C 0.6839(3) 0.0233(5) 0.2192(3) 0.0403(10) Uani 1 1 d . . . C5 C 0.8782(4) -0.2127(5) 0.0030(3) 0.0477(11) Uani 1 1 d . . . C14 C 0.7069(3) -0.3159(4) 0.1097(3) 0.0393(10) Uani 1 1 d . . . C8 C 0.6782(4) 0.1262(5) 0.2889(4) 0.0514(12) Uani 1 1 d . . . H8A H 0.7310 0.1388 0.3365 0.062 Uiso 1 1 calc R . . C19 C 0.7663(4) -0.3962(5) 0.1729(4) 0.0481(11) Uani 1 1 d . . . H19A H 0.8089 -0.3561 0.2216 0.058 Uiso 1 1 calc R . . C12 C 0.6037(3) 0.0052(5) 0.1503(3) 0.0415(10) Uani 1 1 d . . . C18 C 0.7636(4) -0.5353(5) 0.1652(4) 0.0564(13) Uani 1 1 d . . . H18A H 0.8049 -0.5882 0.2077 0.068 Uiso 1 1 calc R . . C10 C 0.5141(4) 0.1906(6) 0.2171(4) 0.0609(14) Uani 1 1 d . . . H10A H 0.4571 0.2481 0.2169 0.073 Uiso 1 1 calc R . . C11 C 0.5175(3) 0.0878(5) 0.1472(4) 0.0513(12) Uani 1 1 d . . . H11A H 0.4643 0.0745 0.1001 0.062 Uiso 1 1 calc R . . C16 C 0.6377(4) -0.5161(5) 0.0320(4) 0.0540(13) Uani 1 1 d . . . H16A H 0.5933 -0.5565 -0.0149 0.065 Uiso 1 1 calc R . . C17 C 0.6991(4) -0.5952(5) 0.0940(4) 0.0565(13) Uani 1 1 d . . . H17A H 0.6971 -0.6886 0.0880 0.068 Uiso 1 1 calc R . . C9 C 0.5926(4) 0.2112(6) 0.2876(4) 0.0644(15) Uani 1 1 d . . . H9A H 0.5882 0.2817 0.3339 0.077 Uiso 1 1 calc R . . C1 C 1.0353(4) -0.3327(6) 0.0682(5) 0.0669(15) Uani 1 1 d . . . H1A H 1.0822 -0.3250 0.1250 0.100 Uiso 1 1 calc R . . H1B H 1.0731 -0.3228 0.0062 0.100 Uiso 1 1 calc R . . H1C H 1.0024 -0.4195 0.0694 0.100 Uiso 1 1 calc R . . 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 Cl1 0.0542(7) 0.0377(7) 0.0647(8) 0.0006(5) 0.0032(5) -0.0108(5) Cl2 0.0639(9) 0.0798(10) 0.0471(7) 0.0286(6) -0.0134(6) -0.0135(7) O3 0.0356(16) 0.0444(18) 0.0473(18) 0.0015(14) -0.0114(13) 0.0003(13) O2 0.0421(18) 0.072(2) 0.058(2) 0.0027(17) -0.0191(16) 0.0041(16) N 0.0390(19) 0.043(2) 0.051(2) -0.0041(18) 0.0033(16) 0.0003(16) C3 0.032(2) 0.037(2) 0.036(2) 0.0021(18) -0.0045(16) -0.0042(17) C13 0.033(2) 0.043(2) 0.036(2) 0.0057(18) -0.0049(16) -0.0018(18) C4 0.037(2) 0.044(2) 0.035(2) 0.0054(19) -0.0052(17) -0.0068(18) C15 0.047(3) 0.047(3) 0.047(3) 0.000(2) -0.005(2) -0.004(2) C2 0.034(2) 0.040(2) 0.046(2) 0.0088(19) 0.0000(18) -0.0067(18) O1 0.062(2) 0.086(3) 0.054(2) -0.028(2) 0.0110(17) -0.014(2) C6 0.039(2) 0.039(2) 0.037(2) 0.0061(18) -0.0022(17) -0.0050(18) C7 0.036(2) 0.047(3) 0.038(2) 0.0038(19) -0.0006(17) 0.0008(19) C5 0.045(2) 0.058(3) 0.041(2) -0.006(2) 0.0059(19) -0.012(2) C14 0.037(2) 0.045(2) 0.037(2) 0.0035(19) 0.0039(17) -0.0044(19) C8 0.050(3) 0.063(3) 0.042(2) -0.002(2) 0.004(2) 0.002(2) C19 0.049(3) 0.046(3) 0.049(3) 0.004(2) -0.008(2) -0.003(2) C12 0.034(2) 0.045(3) 0.046(2) 0.007(2) 0.0028(18) -0.0030(18) C18 0.061(3) 0.041(3) 0.068(3) 0.012(2) -0.001(3) 0.005(2) C10 0.054(3) 0.061(3) 0.069(3) -0.001(3) 0.015(3) 0.015(3) C11 0.036(2) 0.056(3) 0.062(3) 0.009(2) -0.002(2) 0.003(2) C16 0.051(3) 0.053(3) 0.059(3) -0.014(2) -0.001(2) -0.009(2) C17 0.062(3) 0.033(3) 0.074(4) -0.003(2) 0.008(3) -0.002(2) C9 0.065(3) 0.069(4) 0.059(3) -0.012(3) 0.013(3) 0.006(3) C1 0.062(3) 0.058(3) 0.081(4) -0.005(3) 0.009(3) 0.015(3) _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 Cl1 C3 1.759(4) . ? Cl2 C4 1.750(4) . ? O3 C12 1.380(5) . ? O3 C13 1.435(5) . ? O2 C2 1.200(5) . ? N C2 1.380(6) . ? N C5 1.389(6) . ? N C1 1.447(6) . ? C3 C2 1.531(6) . ? C3 C4 1.541(5) . ? C3 C6 1.552(6) . ? C13 C14 1.504(6) . ? C13 C6 1.559(6) . ? C13 C4 1.605(6) . ? C4 C5 1.511(7) . ? C15 C14 1.384(6) . ? C15 C16 1.386(7) . ? C15 H15A 0.9300 . ? O1 C5 1.203(5) . ? C6 C7 1.509(6) . ? C6 H6A 0.9800 . ? C7 C8 1.375(7) . ? C7 C12 1.382(6) . ? C14 C19 1.379(6) . ? C8 C9 1.387(7) . ? C8 H8A 0.9300 . ? C19 C18 1.383(7) . ? C19 H19A 0.9300 . ? C12 C11 1.381(6) . ? C18 C17 1.382(7) . ? C18 H18A 0.9300 . ? C10 C11 1.373(8) . ? C10 C9 1.383(8) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C16 C17 1.376(7) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C9 H9A 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 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 C12 O3 C13 108.0(3) . . ? C2 N C5 113.9(4) . . ? C2 N C1 122.9(4) . . ? C5 N C1 123.2(4) . . ? C2 C3 C4 103.5(3) . . ? C2 C3 C6 113.5(3) . . ? C4 C3 C6 91.7(3) . . ? C2 C3 Cl1 108.4(3) . . ? C4 C3 Cl1 120.6(3) . . ? C6 C3 Cl1 117.8(3) . . ? O3 C13 C14 109.7(3) . . ? O3 C13 C6 108.0(3) . . ? C14 C13 C6 122.6(4) . . ? O3 C13 C4 111.7(3) . . ? C14 C13 C4 114.3(4) . . ? C6 C13 C4 89.0(3) . . ? C5 C4 C3 106.0(3) . . ? C5 C4 C13 112.7(4) . . ? C3 C4 C13 88.5(3) . . ? C5 C4 Cl2 111.8(3) . . ? C3 C4 Cl2 119.2(3) . . ? C13 C4 Cl2 116.4(3) . . ? C14 C15 C16 120.1(5) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? O2 C2 N 125.6(4) . . ? O2 C2 C3 125.8(4) . . ? N C2 C3 108.6(4) . . ? C7 C6 C3 115.5(3) . . ? C7 C6 C13 101.6(3) . . ? C3 C6 C13 89.8(3) . . ? C7 C6 H6A 115.5 . . ? C3 C6 H6A 115.5 . . ? C13 C6 H6A 115.5 . . ? C8 C7 C12 119.4(4) . . ? C8 C7 C6 131.8(4) . . ? C12 C7 C6 108.8(4) . . ? O1 C5 N 124.5(5) . . ? O1 C5 C4 127.9(4) . . ? N C5 C4 107.6(4) . . ? C19 C14 C15 119.0(4) . . ? C19 C14 C13 121.5(4) . . ? C15 C14 C13 119.4(4) . . ? C7 C8 C9 119.3(5) . . ? C7 C8 H8A 120.4 . . ? C9 C8 H8A 120.4 . . ? C14 C19 C18 121.2(5) . . ? C14 C19 H19A 119.4 . . ? C18 C19 H19A 119.4 . . ? O3 C12 C11 123.8(4) . . ? O3 C12 C7 113.5(4) . . ? C11 C12 C7 122.7(4) . . ? C17 C18 C19 119.5(5) . . ? C17 C18 H18A 120.3 . . ? C19 C18 H18A 120.3 . . ? C11 C10 C9 122.1(5) . . ? C11 C10 H10A 118.9 . . ? C9 C10 H10A 118.9 . . ? C10 C11 C12 116.8(5) . . ? C10 C11 H11A 121.6 . . ? C12 C11 H11A 121.6 . . ? C17 C16 C15 120.4(5) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C16 C17 C18 119.8(5) . . ? C16 C17 H17A 120.1 . . ? C18 C17 H17A 120.1 . . ? C10 C9 C8 119.7(5) . . ? C10 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? N C1 H1A 109.5 . . ? N C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.501 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.131 #===END data_5b _database_code_depnum_ccdc_archive 'CCDC 280980' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H11 N O3' _chemical_formula_sum 'C19 H11 N O3' _chemical_formula_weight 301.29 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5260(19) _cell_length_b 18.319(4) _cell_length_c 7.9420(16) _cell_angle_alpha 90.00 _cell_angle_beta 96.25(3) _cell_angle_gamma 90.00 _cell_volume 1377.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 25.07 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.932 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details '(XCAD4; Harms & Wocadlo,1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2629 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0836 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.07 _reflns_number_total 2439 _reflns_number_gt 1361 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CAD4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD4 Software' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PLATON (Spek, 2003)' _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^)+(0.0445P)^2^+1.75P] 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_extinction_coef ? _refine_ls_number_reflns 2439 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1278 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1572 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O3 O 0.8887(3) -0.00696(13) 0.2387(3) 0.0421(7) Uani 1 1 d . . . O2 O 0.5007(3) 0.11644(15) 0.7028(3) 0.0571(8) Uani 1 1 d . . . O1 O 0.7119(3) 0.14345(14) 0.2186(3) 0.0537(8) Uani 1 1 d . . . C4 C 0.6616(4) 0.03542(19) 0.5720(4) 0.0373(9) Uani 1 1 d . . . N N 0.5898(3) 0.14674(16) 0.4538(4) 0.0424(8) Uani 1 1 d . . . C12 C 0.9462(4) -0.11209(19) 0.3894(4) 0.0373(9) Uani 1 1 d . . . C3 C 0.7243(4) 0.04527(19) 0.4241(4) 0.0374(9) Uani 1 1 d . . . C7 C 0.9683(4) -0.0708(2) 0.2469(4) 0.0390(9) Uani 1 1 d . . . C19 C 0.6881(4) -0.0259(2) 0.6795(4) 0.0379(9) Uani 1 1 d . . . C6 C 0.8171(4) -0.00897(19) 0.3796(4) 0.0372(9) Uani 1 1 d . . . C10 C 1.1092(4) -0.1993(2) 0.2980(5) 0.0507(11) Uani 1 1 d . . . H13A H 1.1573 -0.2433 0.3130 0.061 Uiso 1 1 calc R . . C11 C 1.0190(4) -0.1781(2) 0.4119(5) 0.0447(10) Uani 1 1 d . . . H12A H 1.0063 -0.2077 0.5042 0.054 Uiso 1 1 calc R . . C13 C 0.8471(4) -0.07076(19) 0.4765(4) 0.0366(9) Uani 1 1 d . . . C14 C 0.7844(4) -0.08043(19) 0.6324(4) 0.0374(9) Uani 1 1 d . . . C5 C 0.5741(4) 0.1011(2) 0.5928(5) 0.0423(9) Uani 1 1 d . . . C2 C 0.6791(4) 0.1160(2) 0.3463(5) 0.0409(9) Uani 1 1 d . . . C1 C 0.5267(4) 0.2184(2) 0.4293(5) 0.0556(11) Uani 1 1 d . . . H7A H 0.5520 0.2391 0.3257 0.083 Uiso 1 1 calc R . . H7B H 0.5605 0.2494 0.5225 0.083 Uiso 1 1 calc R . . H7C H 0.4259 0.2143 0.4236 0.083 Uiso 1 1 calc R . . C15 C 0.8155(4) -0.1405(2) 0.7402(5) 0.0486(10) Uani 1 1 d . . . H6A H 0.8779 -0.1761 0.7111 0.058 Uiso 1 1 calc R . . C16 C 0.7542(4) -0.1469(2) 0.8885(5) 0.0563(11) Uani 1 1 d . . . H5A H 0.7761 -0.1866 0.9593 0.068 Uiso 1 1 calc R . . C17 C 0.6594(4) -0.0942(2) 0.9335(5) 0.0578(12) Uani 1 1 d . . . H4A H 0.6176 -0.0996 1.0332 0.069 Uiso 1 1 calc R . . C18 C 0.6274(4) -0.0351(2) 0.8330(5) 0.0497(10) Uani 1 1 d . . . H3A H 0.5648 -0.0002 0.8657 0.060 Uiso 1 1 calc R . . C8 C 1.0593(4) -0.0897(2) 0.1288(5) 0.0450(10) Uani 1 1 d . . . H2A H 1.0719 -0.0604 0.0360 0.054 Uiso 1 1 calc R . . C9 C 1.1295(4) -0.1547(2) 0.1585(5) 0.0494(10) Uani 1 1 d . . . H1A H 1.1925 -0.1698 0.0839 0.059 Uiso 1 1 calc R . . 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 O3 0.0496(16) 0.0439(15) 0.0351(14) 0.0014(11) 0.0153(12) 0.0026(13) O2 0.0586(18) 0.0645(19) 0.0523(17) -0.0056(15) 0.0236(16) 0.0047(15) O1 0.0644(19) 0.0480(16) 0.0514(17) 0.0107(14) 0.0177(15) -0.0016(14) C4 0.037(2) 0.040(2) 0.035(2) -0.0018(17) 0.0093(17) -0.0055(17) N 0.0467(19) 0.0401(17) 0.0420(18) 0.0005(15) 0.0116(16) 0.0033(15) C12 0.041(2) 0.036(2) 0.034(2) -0.0003(17) 0.0019(17) -0.0053(17) C3 0.037(2) 0.037(2) 0.039(2) 0.0001(16) 0.0067(17) -0.0035(17) C7 0.041(2) 0.038(2) 0.039(2) -0.0032(17) 0.0037(18) 0.0006(17) C19 0.035(2) 0.047(2) 0.033(2) -0.0027(17) 0.0090(16) -0.0109(17) C6 0.039(2) 0.042(2) 0.0322(19) -0.0009(17) 0.0111(17) -0.0076(17) C10 0.056(3) 0.046(2) 0.049(2) -0.007(2) 0.003(2) 0.010(2) C11 0.051(2) 0.039(2) 0.044(2) 0.0019(18) 0.0044(19) 0.0001(19) C13 0.038(2) 0.038(2) 0.035(2) 0.0007(17) 0.0062(16) -0.0055(17) C14 0.038(2) 0.041(2) 0.0326(19) 0.0032(17) 0.0024(16) -0.0093(18) C5 0.039(2) 0.048(2) 0.040(2) -0.0057(19) 0.0048(19) -0.0056(19) C2 0.042(2) 0.042(2) 0.040(2) 0.0014(18) 0.0065(19) -0.0055(18) C1 0.056(3) 0.048(2) 0.062(3) 0.000(2) 0.008(2) 0.010(2) C15 0.049(2) 0.052(2) 0.046(2) 0.009(2) 0.008(2) -0.002(2) C16 0.062(3) 0.061(3) 0.048(3) 0.012(2) 0.012(2) 0.002(2) C17 0.066(3) 0.069(3) 0.040(2) 0.011(2) 0.017(2) -0.010(2) C18 0.053(3) 0.057(3) 0.041(2) 0.002(2) 0.014(2) -0.002(2) C8 0.049(2) 0.051(2) 0.037(2) -0.0042(19) 0.0125(18) 0.002(2) C9 0.048(2) 0.053(3) 0.047(2) -0.011(2) 0.008(2) 0.007(2) _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 O3 C6 1.373(4) . ? O3 C7 1.391(4) . ? O2 C5 1.210(4) . ? O1 C2 1.203(4) . ? C4 C3 1.387(5) . ? C4 C19 1.417(5) . ? C4 C5 1.484(5) . ? N C2 1.389(4) . ? N C5 1.405(4) . ? N C1 1.448(5) . ? C12 C11 1.396(5) . ? C12 C7 1.396(5) . ? C12 C13 1.443(5) . ? C3 C6 1.400(5) . ? C3 C2 1.479(5) . ? C7 C8 1.389(5) . ? C19 C18 1.415(5) . ? C19 C14 1.433(5) . ? C6 C13 1.381(5) . ? C10 C11 1.369(5) . ? C10 C9 1.406(5) . ? C10 H13A 0.9300 . ? C11 H12A 0.9300 . ? C13 C14 1.443(5) . ? C14 C15 1.405(5) . ? C1 H7A 0.9600 . ? C1 H7B 0.9600 . ? C1 H7C 0.9600 . ? C15 C16 1.375(5) . ? C15 H6A 0.9300 . ? C16 C17 1.394(6) . ? C16 H5A 0.9300 . ? C17 C18 1.360(5) . ? C17 H4A 0.9300 . ? C18 H3A 0.9300 . ? C8 C9 1.374(5) . ? C8 H2A 0.9300 . ? C9 H1A 0.9300 . ? 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 C6 O3 C7 104.8(3) . . ? C3 C4 C19 123.3(3) . . ? C3 C4 C5 106.7(3) . . ? C19 C4 C5 129.9(3) . . ? C2 N C5 111.5(3) . . ? C2 N C1 123.9(3) . . ? C5 N C1 124.5(3) . . ? C11 C12 C7 117.1(3) . . ? C11 C12 C13 137.3(3) . . ? C7 C12 C13 105.6(3) . . ? C4 C3 C6 117.6(3) . . ? C4 C3 C2 109.6(3) . . ? C6 C3 C2 132.8(3) . . ? C8 C7 O3 123.7(3) . . ? C8 C7 C12 125.0(3) . . ? O3 C7 C12 111.3(3) . . ? C18 C19 C4 123.4(3) . . ? C18 C19 C14 118.4(3) . . ? C4 C19 C14 118.2(3) . . ? O3 C6 C13 112.6(3) . . ? O3 C6 C3 124.7(3) . . ? C13 C6 C3 122.6(3) . . ? C11 C10 C9 120.4(4) . . ? C11 C10 H13A 119.8 . . ? C9 C10 H13A 119.8 . . ? C10 C11 C12 119.9(4) . . ? C10 C11 H12A 120.0 . . ? C12 C11 H12A 120.0 . . ? C6 C13 C14 119.9(3) . . ? C6 C13 C12 105.6(3) . . ? C14 C13 C12 134.4(3) . . ? C15 C14 C19 119.0(3) . . ? C15 C14 C13 122.7(3) . . ? C19 C14 C13 118.4(3) . . ? O2 C5 N 123.3(4) . . ? O2 C5 C4 130.1(4) . . ? N C5 C4 106.6(3) . . ? O1 C2 N 125.5(3) . . ? O1 C2 C3 128.9(3) . . ? N C2 C3 105.6(3) . . ? N C1 H7A 109.5 . . ? N C1 H7B 109.5 . . ? H7A C1 H7B 109.5 . . ? N C1 H7C 109.5 . . ? H7A C1 H7C 109.5 . . ? H7B C1 H7C 109.5 . . ? C16 C15 C14 120.5(4) . . ? C16 C15 H6A 119.7 . . ? C14 C15 H6A 119.7 . . ? C15 C16 C17 120.5(4) . . ? C15 C16 H5A 119.8 . . ? C17 C16 H5A 119.8 . . ? C18 C17 C16 120.7(4) . . ? C18 C17 H4A 119.6 . . ? C16 C17 H4A 119.6 . . ? C17 C18 C19 120.9(4) . . ? C17 C18 H3A 119.6 . . ? C19 C18 H3A 119.6 . . ? C9 C8 C7 115.3(4) . . ? C9 C8 H2A 122.3 . . ? C7 C8 H2A 122.3 . . ? C8 C9 C10 122.2(4) . . ? C8 C9 H1A 118.9 . . ? C10 C9 H1A 118.9 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.232 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.056