# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address 'Hans-Ulrich Reissig' ; Institut f\"ur Chemie / Organische Chemie Freie Universit\"at Berlin Takustr. 3 14195 Berlin Bundesrepublik Deutschland ; 'Irene Brudgam' ; Institut f\"ur Chemie / Anorganische Chemie Freie Universit\"at Berlin Fabeckstr. 34 14195 Berlin Bundesrepublik Deutschland ; 'Jyotirmayee Dash' ; Institut f\"ur Chemie / Organische Chemie Freie Universit\"at Berlin Takustr. 3 14195 Berlin Bundesrepublik Deutschland ; 'Christian Eidamshaus' ; Institut f\"ur Chemie / Organische Chemie Freie Universit\"at Berlin Takustr. 3 14195 Berlin Bundesrepublik Deutschland ; 'Tilman Lechel' ; Indian Institute of Science, Education and Research Kolkata Mohanpur Campus Mohanpur 741252 West Bengal India ; _publ_contact_author_name 'Hans-Ulrich Reissig' _publ_contact_author_email HANS.REISSIG@CHEMIE.FU-BERLIN.DE _publ_section_title ; Scope and Limitations of a Three-Component Synthesis of Highly Functionalised ?-Alkoxy-?-ketoenamides - Flexible Precursors for Cyclisations to 4-Hydroxypyridine Derivatives and their Palladium-Catalysed Coupling Reactions ; # Attachment '5.CIF' #1. SUBMISSION DETAILS _publ_contact_author ; Prof. Dr. Hans-Ulrich Reissig Institut f\"ur Chemie / Organische Chemie Freie Universit\"at Berlin Takustr. 3 14195 Berlin Bundesrepublik Deutschland ; _publ_contact_author_fax '049 30 83855367' _publ_contact_author_phone '049 30 83855330' _publ_requested_category ; Organic Chemistry ; _publ_requested_coeditor_name ? data_orgda7m _database_code_depnum_ccdc_archive 'CCDC 756788' #TrackingRef '5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (E)-N-(2-Methoxy-3-oxobut-1-enyl)picolinamide _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 N2 O3' _chemical_formula_weight 220.23 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.038(5) _cell_length_b 8.521(5) _cell_length_c 8.678(5) _cell_angle_alpha 73.591(5) _cell_angle_beta 81.419(5) _cell_angle_gamma 69.809(5) _cell_volume 534.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 30.45 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .5 _exptl_crystal_size_mid .19 _exptl_crystal_size_min .15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area Detector' _diffrn_measurement_method 'phi and omega scans with .3 deg in omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time '5 sec/frame' _diffrn_standards_decay_% ? _diffrn_reflns_number 6027 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 30.55 _reflns_number_total 3200 _reflns_number_gt 2146 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1153P)^2^+0.0220P] 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 3200 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.2042 _refine_ls_wR_factor_gt 0.1872 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 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 0.13098(16) 0.00216(16) 0.67699(16) 0.0409(4) Uani 1 1 d . . . O2 O -0.15426(15) 0.51308(15) 0.22506(14) 0.0345(3) Uani 1 1 d . . . O3 O 0.26947(17) 0.50322(16) 0.29350(16) 0.0401(3) Uani 1 1 d . . . N1 N 0.50058(19) 0.15173(18) 0.63377(17) 0.0317(3) Uani 1 1 d . . . N8 N 0.19600(17) 0.23229(17) 0.50237(16) 0.0292(3) Uani 1 1 d . . . H8 H 0.2732 0.2857 0.4729 0.035 Uiso 1 1 calc R . . C2 C 0.4091(2) 0.0413(2) 0.69436(18) 0.0258(3) Uani 1 1 d . . . C3 C 0.4684(2) -0.1075(2) 0.8167(2) 0.0314(4) Uani 1 1 d . . . H3 H 0.4006 -0.1809 0.8561 0.038 Uiso 1 1 calc R . . C4 C 0.6302(2) -0.1441(2) 0.8786(2) 0.0335(4) Uani 1 1 d . . . H4 H 0.6734 -0.2426 0.9604 0.040 Uiso 1 1 calc R . . C5 C 0.7263(2) -0.0316(2) 0.8167(2) 0.0344(4) Uani 1 1 d . . . H5 H 0.8358 -0.0528 0.8554 0.041 Uiso 1 1 calc R . . C6 C 0.6555(2) 0.1144(2) 0.6951(2) 0.0356(4) Uani 1 1 d . . . H6 H 0.7205 0.1903 0.6543 0.043 Uiso 1 1 calc R . . C7 C 0.2322(2) 0.0871(2) 0.6254(2) 0.0281(4) Uani 1 1 d . . . C9 C 0.0394(2) 0.2980(2) 0.4224(2) 0.0293(4) Uani 1 1 d . . . H9 H -0.0429 0.2387 0.4536 0.035 Uiso 1 1 calc R . . C10 C 0.0004(2) 0.4437(2) 0.3014(2) 0.0288(4) Uani 1 1 d . . . C11 C 0.1256(2) 0.5434(2) 0.2356(2) 0.0298(4) Uani 1 1 d . . . C12 C 0.0709(3) 0.6938(2) 0.0925(2) 0.0393(4) Uani 1 1 d . . . H12A H 0.1593 0.7510 0.0644 0.059 Uiso 1 1 calc R . . H12B H -0.0408 0.7734 0.1183 0.059 Uiso 1 1 calc R . . H12C H 0.0593 0.6534 0.0033 0.059 Uiso 1 1 calc R . . C13 C -0.2937(2) 0.4435(2) 0.2958(2) 0.0375(4) Uani 1 1 d . . . H13A H -0.2575 0.3242 0.2942 0.056 Uiso 1 1 calc R . . H13B H -0.3979 0.5064 0.2359 0.056 Uiso 1 1 calc R . . H13C H -0.3197 0.4532 0.4050 0.056 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 O1 0.0283(6) 0.0392(7) 0.0519(8) 0.0001(6) -0.0036(6) -0.0154(5) O2 0.0258(6) 0.0353(7) 0.0387(7) -0.0031(5) -0.0059(5) -0.0086(5) O3 0.0356(7) 0.0369(7) 0.0493(8) -0.0041(6) -0.0062(6) -0.0172(6) N1 0.0319(7) 0.0287(7) 0.0353(7) -0.0037(5) -0.0040(6) -0.0133(6) N8 0.0237(7) 0.0248(7) 0.0375(7) -0.0055(5) -0.0024(6) -0.0072(5) C2 0.0258(8) 0.0229(7) 0.0289(7) -0.0094(6) 0.0008(6) -0.0068(6) C3 0.0332(9) 0.0286(8) 0.0323(8) -0.0040(6) 0.0000(7) -0.0134(7) C4 0.0381(9) 0.0272(8) 0.0312(8) -0.0020(6) -0.0045(7) -0.0086(7) C5 0.0315(9) 0.0381(9) 0.0346(8) -0.0078(7) -0.0070(7) -0.0113(7) C6 0.0365(9) 0.0360(9) 0.0375(9) -0.0023(7) -0.0047(7) -0.0202(8) C7 0.0237(8) 0.0242(8) 0.0342(8) -0.0080(6) 0.0006(6) -0.0052(6) C9 0.0242(8) 0.0295(8) 0.0360(8) -0.0105(6) -0.0041(6) -0.0081(6) C10 0.0233(8) 0.0311(8) 0.0348(8) -0.0117(6) -0.0034(6) -0.0085(6) C11 0.0301(8) 0.0285(8) 0.0321(8) -0.0104(6) -0.0005(7) -0.0092(7) C12 0.0463(11) 0.0402(10) 0.0337(9) -0.0035(7) -0.0045(8) -0.0204(9) C13 0.0279(9) 0.0355(9) 0.0488(10) -0.0057(8) -0.0081(8) -0.0110(7) _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 C7 1.2256(19) . ? O2 C10 1.361(2) . ? O2 C13 1.426(2) . ? O3 C11 1.228(2) . ? N1 C6 1.328(2) . ? N1 C2 1.336(2) . ? N8 C7 1.361(2) . ? N8 C9 1.391(2) . ? C2 C3 1.391(2) . ? C2 C7 1.507(2) . ? C3 C4 1.383(3) . ? C4 C5 1.378(2) . ? C5 C6 1.391(2) . ? C9 C10 1.355(2) . ? C10 C11 1.485(2) . ? C11 C12 1.501(2) . ? 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 C10 O2 C13 116.73(13) . . ? C6 N1 C2 117.15(15) . . ? C7 N8 C9 122.80(14) . . ? N1 C2 C3 123.19(16) . . ? N1 C2 C7 116.45(14) . . ? C3 C2 C7 120.36(14) . . ? C4 C3 C2 118.72(15) . . ? C5 C4 C3 118.68(15) . . ? C4 C5 C6 118.45(16) . . ? N1 C6 C5 123.82(16) . . ? O1 C7 N8 123.74(15) . . ? O1 C7 C2 122.82(14) . . ? N8 C7 C2 113.44(13) . . ? C10 C9 N8 123.43(15) . . ? C9 C10 O2 124.36(14) . . ? C9 C10 C11 122.99(15) . . ? O2 C10 C11 112.65(14) . . ? O3 C11 C10 121.70(15) . . ? O3 C11 C12 121.13(15) . . ? C10 C11 C12 117.16(15) . . ? 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 C6 N1 C2 C3 0.2(3) . . . . ? C6 N1 C2 C7 179.01(14) . . . . ? N1 C2 C3 C4 -0.4(3) . . . . ? C7 C2 C3 C4 -179.09(14) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C2 N1 C6 C5 0.2(3) . . . . ? C4 C5 C6 N1 -0.5(3) . . . . ? C9 N8 C7 O1 -0.3(3) . . . . ? C9 N8 C7 C2 -179.60(14) . . . . ? N1 C2 C7 O1 -175.56(15) . . . . ? C3 C2 C7 O1 3.3(3) . . . . ? N1 C2 C7 N8 3.7(2) . . . . ? C3 C2 C7 N8 -177.49(15) . . . . ? C7 N8 C9 C10 178.97(16) . . . . ? N8 C9 C10 O2 -177.84(15) . . . . ? N8 C9 C10 C11 3.4(3) . . . . ? C13 O2 C10 C9 11.0(2) . . . . ? C13 O2 C10 C11 -170.17(14) . . . . ? C9 C10 C11 O3 -3.7(3) . . . . ? O2 C10 C11 O3 177.45(15) . . . . ? C9 C10 C11 C12 174.98(15) . . . . ? O2 C10 C11 C12 -3.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 30.55 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.627 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.079 # Attachment '17a.CIF' data_orgda4 _database_code_depnum_ccdc_archive 'CCDC 756789' #TrackingRef '17a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (E)-2-tert-Butyl-3-methoxy-6-methyl-4-styrylpyridine ; _chemical_name_common (E)-2-tert-Butyl-3-methoxy-6-methyl-4-styrylpyridine _chemical_melting_point '393 K' _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 N O' _chemical_formula_weight 281.38 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 orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 13.141(4) _cell_length_b 8.066(2) _cell_length_c 15.156(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1606.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 2.522 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .48 _exptl_crystal_size_mid .47 _exptl_crystal_size_min .43 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-AXS SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14518 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.55 _reflns_number_total 1926 _reflns_number_gt 1774 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker-AXS)' _computing_cell_refinement 'Saint (Bruker-AXS)' _computing_data_reduction 'Saint (Bruker-AXS)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0595P)^2^+0.1367P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(15) _refine_ls_number_reflns 1926 _refine_ls_number_parameters 195 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C2 C -0.00009(11) 0.9676(2) 0.08836(12) 0.0231(3) Uani 1 1 d . . . C3 C 0.03563(11) 0.8786(2) 0.01496(11) 0.0228(3) Uani 1 1 d . . . C4 C 0.08638(11) 0.7276(2) 0.02660(12) 0.0248(3) Uani 1 1 d . . . C5 C 0.10746(12) 0.6794(2) 0.11329(12) 0.0273(4) Uani 1 1 d . . . H5 H 0.1414 0.5777 0.1247 0.033 Uiso 1 1 calc R . . C6 C 0.07848(12) 0.7810(2) 0.18240(12) 0.0272(4) Uani 1 1 d . . . C7 C -0.10819(16) 1.1767(3) 0.16912(14) 0.0394(5) Uani 1 1 d . . . H7C H -0.1520 1.2742 0.1618 0.059 Uiso 1 1 calc R . . H7B H -0.0499 1.2057 0.2064 0.059 Uiso 1 1 calc R . . H7A H -0.1471 1.0873 0.1970 0.059 Uiso 1 1 calc R . . C8 C -0.07018(12) 1.1192(2) 0.07877(12) 0.0273(4) Uani 1 1 d . . . C9 C -0.01412(15) 1.2643(2) 0.03445(16) 0.0387(4) Uani 1 1 d . . . H9A H 0.0483 1.2890 0.0673 0.058 Uiso 1 1 calc R . . H9B H -0.0582 1.3623 0.0341 0.058 Uiso 1 1 calc R . . H9C H 0.0033 1.2342 -0.0263 0.058 Uiso 1 1 calc R . . C10 C -0.16399(13) 1.0713(2) 0.02345(13) 0.0329(4) Uani 1 1 d . . . H10B H -0.2104 1.1661 0.0198 0.049 Uiso 1 1 calc R . . H10A H -0.1990 0.9777 0.0514 0.049 Uiso 1 1 calc R . . H10C H -0.1423 1.0396 -0.0361 0.049 Uiso 1 1 calc R . . C11 C 0.11421(12) 0.6283(2) -0.05077(12) 0.0271(3) Uani 1 1 d . . . H11 H 0.0750 0.6439 -0.1028 0.033 Uiso 1 1 calc R . . C12 C 0.18991(13) 0.5179(2) -0.05453(12) 0.0282(4) Uani 1 1 d . . . H12 H 0.2281 0.5017 -0.0020 0.034 Uiso 1 1 calc R . . C13 C 0.21985(12) 0.41943(19) -0.13138(13) 0.0270(4) Uani 1 1 d . . . C14 C 0.30690(13) 0.3196(2) -0.12670(14) 0.0315(4) Uani 1 1 d . . . H14 H 0.3451 0.3157 -0.0735 0.038 Uiso 1 1 calc R . . C15 C 0.33806(14) 0.2261(2) -0.19872(15) 0.0365(4) Uani 1 1 d . . . H15 H 0.3972 0.1589 -0.1944 0.044 Uiso 1 1 calc R . . C16 C 0.28399(15) 0.2302(2) -0.27624(15) 0.0381(4) Uani 1 1 d . . . H16 H 0.3058 0.1665 -0.3254 0.046 Uiso 1 1 calc R . . C17 C 0.19684(15) 0.3283(2) -0.28238(14) 0.0362(4) Uani 1 1 d . . . H17 H 0.1591 0.3314 -0.3358 0.043 Uiso 1 1 calc R . . C18 C 0.16537(13) 0.4209(2) -0.21086(13) 0.0315(4) Uani 1 1 d . . . H18 H 0.1057 0.4868 -0.2156 0.038 Uiso 1 1 calc R . . C19 C 0.10723(16) 0.7397(3) 0.27622(14) 0.0386(4) Uani 1 1 d . . . H19B H 0.0482 0.7560 0.3147 0.058 Uiso 1 1 calc R . . H19C H 0.1628 0.8123 0.2953 0.058 Uiso 1 1 calc R . . H19A H 0.1294 0.6238 0.2795 0.058 Uiso 1 1 calc R . . C20 C 0.10922(14) 0.9991(3) -0.11156(12) 0.0347(4) Uani 1 1 d . . . H20A H 0.1569 0.9074 -0.1212 0.052 Uiso 1 1 calc R . . H20C H 0.1411 1.0828 -0.0738 0.052 Uiso 1 1 calc R . . H20B H 0.0913 1.0491 -0.1684 0.052 Uiso 1 1 calc R . . N1 N 0.02317(10) 0.91911(19) 0.17030(10) 0.0258(3) Uani 1 1 d . . . O1 O 0.01859(9) 0.93730(15) -0.06945(8) 0.0269(3) 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 C2 0.0215(6) 0.0219(8) 0.0258(8) -0.0007(7) -0.0019(6) -0.0020(6) C3 0.0209(6) 0.0248(7) 0.0226(8) 0.0005(6) -0.0015(6) -0.0023(6) C4 0.0214(7) 0.0246(8) 0.0282(9) -0.0009(7) 0.0005(6) -0.0024(6) C5 0.0265(7) 0.0238(8) 0.0317(9) 0.0044(7) -0.0004(6) 0.0025(6) C6 0.0252(7) 0.0299(8) 0.0265(9) 0.0050(7) -0.0008(6) -0.0003(6) C7 0.0443(10) 0.0406(11) 0.0334(10) -0.0078(9) -0.0040(8) 0.0177(8) C8 0.0288(7) 0.0257(8) 0.0275(9) -0.0010(7) -0.0037(7) 0.0044(6) C9 0.0471(10) 0.0248(8) 0.0443(11) 0.0040(8) -0.0022(9) 0.0016(7) C10 0.0277(8) 0.0389(10) 0.0320(10) -0.0018(8) -0.0057(7) 0.0082(7) C11 0.0276(8) 0.0267(8) 0.0270(9) -0.0017(7) -0.0002(6) -0.0015(6) C12 0.0289(8) 0.0262(8) 0.0296(9) 0.0013(7) 0.0018(7) -0.0012(6) C13 0.0271(8) 0.0208(7) 0.0331(9) 0.0015(7) 0.0051(7) -0.0019(6) C14 0.0292(8) 0.0289(8) 0.0366(10) 0.0029(8) 0.0017(7) 0.0009(7) C15 0.0315(8) 0.0315(9) 0.0464(12) -0.0017(9) 0.0080(8) 0.0060(7) C16 0.0394(10) 0.0349(9) 0.0400(11) -0.0068(9) 0.0119(8) 0.0008(7) C17 0.0387(10) 0.0366(10) 0.0334(10) -0.0021(8) 0.0009(8) -0.0020(8) C18 0.0299(8) 0.0286(8) 0.0359(10) 0.0006(8) 0.0015(7) 0.0027(7) C19 0.0429(10) 0.0443(11) 0.0287(10) 0.0069(9) -0.0029(8) 0.0117(8) C20 0.0358(9) 0.0402(10) 0.0282(10) 0.0073(8) 0.0040(7) 0.0017(8) N1 0.0258(6) 0.0276(7) 0.0242(7) 0.0003(6) -0.0019(5) 0.0007(5) O1 0.0273(6) 0.0311(6) 0.0223(6) 0.0021(5) -0.0032(5) 0.0037(5) _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 C2 N1 1.337(2) . ? C2 C3 1.405(2) . ? C2 C8 1.538(2) . ? C3 O1 1.383(2) . ? C3 C4 1.400(2) . ? C4 C5 1.398(3) . ? C4 C11 1.466(2) . ? C5 C6 1.383(3) . ? C6 N1 1.343(2) . ? C6 C19 1.509(3) . ? C7 C8 1.530(3) . ? C8 C9 1.538(3) . ? C8 C10 1.540(2) . ? C11 C12 1.337(2) . ? C12 C13 1.464(3) . ? C13 C14 1.401(2) . ? C13 C18 1.401(3) . ? C14 C15 1.388(3) . ? C15 C16 1.373(3) . ? C16 C17 1.395(3) . ? C17 C18 1.380(3) . ? C20 O1 1.440(2) . ? 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 N1 C2 C3 120.65(14) . . ? N1 C2 C8 117.19(15) . . ? C3 C2 C8 122.12(15) . . ? O1 C3 C4 119.47(15) . . ? O1 C3 C2 120.24(14) . . ? C4 C3 C2 120.27(15) . . ? C5 C4 C3 117.05(15) . . ? C5 C4 C11 123.41(15) . . ? C3 C4 C11 119.54(16) . . ? C6 C5 C4 119.52(15) . . ? N1 C6 C5 122.48(16) . . ? N1 C6 C19 116.58(16) . . ? C5 C6 C19 120.94(16) . . ? C7 C8 C9 108.44(17) . . ? C7 C8 C2 110.63(15) . . ? C9 C8 C2 111.09(14) . . ? C7 C8 C10 107.59(15) . . ? C9 C8 C10 109.67(16) . . ? C2 C8 C10 109.34(14) . . ? C12 C11 C4 125.70(16) . . ? C11 C12 C13 126.56(16) . . ? C14 C13 C18 117.75(17) . . ? C14 C13 C12 119.42(17) . . ? C18 C13 C12 122.83(15) . . ? C15 C14 C13 120.88(19) . . ? C16 C15 C14 120.47(17) . . ? C15 C16 C17 119.69(18) . . ? C18 C17 C16 120.04(19) . . ? C17 C18 C13 121.17(17) . . ? C2 N1 C6 119.53(15) . . ? C3 O1 C20 113.25(13) . . ? 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 N1 C2 C3 O1 -174.46(14) . . . . ? C8 C2 C3 O1 7.9(2) . . . . ? N1 C2 C3 C4 7.2(2) . . . . ? C8 C2 C3 C4 -170.39(14) . . . . ? O1 C3 C4 C5 175.91(14) . . . . ? C2 C3 C4 C5 -5.7(2) . . . . ? O1 C3 C4 C11 -4.4(2) . . . . ? C2 C3 C4 C11 173.98(14) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? C11 C4 C5 C6 179.95(16) . . . . ? C4 C5 C6 N1 5.5(2) . . . . ? C4 C5 C6 C19 -175.13(17) . . . . ? N1 C2 C8 C7 -5.2(2) . . . . ? C3 C2 C8 C7 172.45(15) . . . . ? N1 C2 C8 C9 115.27(18) . . . . ? C3 C2 C8 C9 -67.0(2) . . . . ? N1 C2 C8 C10 -123.55(17) . . . . ? C3 C2 C8 C10 54.1(2) . . . . ? C5 C4 C11 C12 -25.1(3) . . . . ? C3 C4 C11 C12 155.22(16) . . . . ? C4 C11 C12 C13 -179.04(15) . . . . ? C11 C12 C13 C14 174.36(17) . . . . ? C11 C12 C13 C18 -5.2(3) . . . . ? C18 C13 C14 C15 0.3(3) . . . . ? C12 C13 C14 C15 -179.25(17) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C14 C15 C16 C17 -0.3(3) . . . . ? C15 C16 C17 C18 0.1(3) . . . . ? C16 C17 C18 C13 0.4(3) . . . . ? C14 C13 C18 C17 -0.6(3) . . . . ? C12 C13 C18 C17 178.99(17) . . . . ? C3 C2 N1 C6 -2.2(2) . . . . ? C8 C2 N1 C6 175.57(14) . . . . ? C5 C6 N1 C2 -4.2(2) . . . . ? C19 C6 N1 C2 176.37(15) . . . . ? C4 C3 O1 C20 -73.19(19) . . . . ? C2 C3 O1 C20 108.47(17) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.200 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.032