# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'M Maier' _publ_contact_author_email MARTIN.E.MAIER@UNI-TUEBINGEN.DE _publ_section_title ; Formation of pentacyclic structures by a domino sequence on cyclic enamides ; loop_ _publ_author_name 'M Maier' 'Gedu Satyanarayana' # Attachment 'journal.cif' data_maigs149b _database_code_depnum_ccdc_archive 'CCDC 710107' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N O' _chemical_formula_weight 303.39 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' 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' H H 0.0000 0.0000 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.3172(13) _cell_length_b 7.6048(6) _cell_length_c 18.468(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.156(9) _cell_angle_gamma 90.00 _cell_volume 1541.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16237 _cell_measurement_theta_min 4.05 _cell_measurement_theta_max 54.44 _exptl_crystal_description bloc _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; less intensitiy for high sin theta range ; _diffrn_ambient_temperature 173(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 'Stoe IPDSII' _diffrn_measurement_method omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21754 _diffrn_reflns_av_R_equivalents 0.0666 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 26.77 _reflns_number_total 3269 _reflns_number_gt 2821 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDSII' _computing_cell_refinement x-Area _computing_data_reduction X-Area _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL, ZORTEP' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.8361P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment iso _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3269 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.186 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.04402(14) 0.5160(2) -0.11091(9) 0.0188(3) Uani 1 d . . . C2 C 0.00808(16) 0.3777(2) -0.16073(10) 0.0254(4) Uani 1 d . . . H2 H 0.0439(19) 0.261(3) -0.1510(11) 0.029(5) Uiso 1 d . . . C3 C -0.08166(16) 0.4079(3) -0.22600(10) 0.0283(4) Uani 1 d . . . H31 H -0.1045(19) 0.314(3) -0.2597(12) 0.033(6) Uiso 1 d . . . C4 C -0.13587(16) 0.5723(3) -0.24088(10) 0.0284(4) Uani 1 d . . . H4 H -0.197(2) 0.591(3) -0.2854(13) 0.037(6) Uiso 1 d . . . C5 C -0.10022(16) 0.7105(2) -0.19115(10) 0.0254(4) Uani 1 d . . . H5 H -0.1371(19) 0.825(3) -0.2007(12) 0.030(5) Uiso 1 d . . . C6 C -0.00930(14) 0.6810(2) -0.12639(9) 0.0196(3) Uani 1 d . . . C7 C 0.04298(15) 0.8094(2) -0.06495(10) 0.0213(3) Uani 1 d . . . H7A H -0.0199(17) 0.854(2) -0.0410(10) 0.019(5) Uiso 1 d . . . H7B H 0.0849(18) 0.911(3) -0.0839(11) 0.025(5) Uiso 1 d . . . N8 N 0.13210(12) 0.70032(18) -0.01301(8) 0.0196(3) Uani 1 d . . . C9 C 0.13250(14) 0.5138(2) -0.03513(9) 0.0172(3) Uani 1 d . . . H9 H 0.0972(16) 0.444(2) 0.0013(10) 0.016(4) Uiso 1 d . . . C10 C 0.19385(15) 0.7533(2) 0.05558(9) 0.0203(3) Uani 1 d . . . C11 C 0.28288(16) 0.6154(2) 0.09499(9) 0.0225(4) Uani 1 d . . . H11A H 0.3395(18) 0.671(3) 0.1369(11) 0.024(5) Uiso 1 d . . . H11B H 0.2380(19) 0.522(3) 0.1157(12) 0.032(5) Uiso 1 d . . . C12 C 0.35005(15) 0.5367(2) 0.03957(9) 0.0205(3) Uani 1 d . . . H12A H 0.3901(18) 0.635(3) 0.0199(11) 0.022(5) Uiso 1 d . . . H12B H 0.4159(18) 0.455(3) 0.0662(11) 0.022(5) Uiso 1 d . . . C13 C 0.26390(14) 0.4369(2) -0.02604(9) 0.0171(3) Uani 1 d . . . C14 C 0.31022(14) 0.4571(2) -0.09680(9) 0.0183(3) Uani 1 d . . . C15 C 0.35399(14) 0.3143(2) -0.13032(9) 0.0201(3) Uani 1 d . . . C16 C 0.35868(17) 0.1300(2) -0.09870(11) 0.0269(4) Uani 1 d . . . H16A H 0.285(2) 0.062(3) -0.1261(13) 0.037(6) Uiso 1 d . . . H16B H 0.431(2) 0.069(3) -0.1082(12) 0.036(6) Uiso 1 d . . . C17 C 0.36179(16) 0.1323(2) -0.01611(10) 0.0248(4) Uani 1 d . . . H17A H 0.3555(19) 0.015(3) 0.0021(12) 0.031(5) Uiso 1 d . . . H17B H 0.4421(19) 0.183(3) 0.0131(11) 0.026(5) Uiso 1 d . . . C18 C 0.25576(15) 0.2421(2) -0.00437(10) 0.0210(3) Uani 1 d . . . H18A H 0.1781(18) 0.189(3) -0.0350(11) 0.023(5) Uiso 1 d . . . H18B H 0.2503(17) 0.237(2) 0.0492(11) 0.021(5) Uiso 1 d . . . C19 C 0.31266(15) 0.6248(2) -0.12797(10) 0.0226(4) Uani 1 d . . . H19 H 0.2838(19) 0.729(3) -0.1033(12) 0.030(5) Uiso 1 d . . . C20 C 0.35649(16) 0.6513(3) -0.19087(10) 0.0272(4) Uani 1 d . . . H20 H 0.3561(19) 0.766(3) -0.2118(12) 0.028(5) Uiso 1 d . . . C21 C 0.39928(17) 0.5085(3) -0.22419(10) 0.0292(4) Uani 1 d . . . H21 H 0.433(2) 0.525(3) -0.2690(12) 0.035(6) Uiso 1 d . . . C22 C 0.39727(16) 0.3428(3) -0.19426(10) 0.0261(4) Uani 1 d . . . H22 H 0.4249(19) 0.243(3) -0.2175(12) 0.031(5) Uiso 1 d . . . O23 O 0.18183(11) 0.90045(16) 0.08031(7) 0.0272(3) Uani 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 C1 0.0138(7) 0.0238(8) 0.0195(8) 0.0013(6) 0.0051(6) 0.0002(6) C2 0.0222(8) 0.0268(9) 0.0269(9) -0.0054(7) 0.0055(7) 0.0003(7) C3 0.0238(8) 0.0374(10) 0.0230(9) -0.0080(8) 0.0046(7) -0.0054(8) C4 0.0201(8) 0.0423(11) 0.0202(8) 0.0066(8) 0.0003(7) -0.0061(8) C5 0.0200(8) 0.0292(9) 0.0261(9) 0.0097(7) 0.0039(7) -0.0014(7) C6 0.0160(7) 0.0228(8) 0.0212(8) 0.0031(6) 0.0066(6) -0.0011(6) C7 0.0199(8) 0.0183(8) 0.0246(8) 0.0023(7) 0.0037(7) 0.0024(6) N8 0.0190(7) 0.0175(7) 0.0212(7) -0.0005(5) 0.0027(5) 0.0031(5) C9 0.0170(7) 0.0164(7) 0.0188(8) -0.0006(6) 0.0055(6) 0.0003(6) C10 0.0200(8) 0.0205(8) 0.0216(8) -0.0005(6) 0.0077(6) -0.0017(6) C11 0.0218(8) 0.0264(9) 0.0182(8) -0.0011(7) 0.0028(7) 0.0005(7) C12 0.0165(7) 0.0226(8) 0.0221(8) -0.0002(7) 0.0040(6) 0.0005(7) C13 0.0146(7) 0.0169(7) 0.0196(8) 0.0008(6) 0.0042(6) 0.0006(6) C14 0.0125(7) 0.0210(8) 0.0204(8) 0.0014(6) 0.0024(6) 0.0005(6) C15 0.0149(7) 0.0230(8) 0.0211(8) -0.0017(7) 0.0019(6) 0.0000(6) C16 0.0277(9) 0.0208(9) 0.0337(10) -0.0018(7) 0.0103(8) 0.0056(7) C17 0.0235(8) 0.0191(8) 0.0323(10) 0.0068(7) 0.0074(7) 0.0055(7) C18 0.0201(8) 0.0192(8) 0.0248(9) 0.0041(7) 0.0073(7) 0.0009(6) C19 0.0198(8) 0.0220(8) 0.0267(9) 0.0032(7) 0.0072(7) 0.0025(7) C20 0.0239(8) 0.0290(10) 0.0294(9) 0.0101(8) 0.0078(7) 0.0012(7) C21 0.0251(9) 0.0418(11) 0.0219(9) 0.0047(8) 0.0084(7) -0.0003(8) C22 0.0220(8) 0.0319(10) 0.0251(9) -0.0064(7) 0.0070(7) 0.0016(7) O23 0.0318(7) 0.0213(6) 0.0271(6) -0.0055(5) 0.0047(5) 0.0008(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 C1 C2 1.391(2) . ? C1 C6 1.391(2) . ? C1 C9 1.509(2) . ? C2 C3 1.392(3) . ? C3 C4 1.390(3) . ? C4 C5 1.389(3) . ? C5 C6 1.392(2) . ? C6 C7 1.504(2) . ? C7 N8 1.467(2) . ? N8 C10 1.350(2) . ? N8 C9 1.476(2) . ? C9 C13 1.568(2) . ? C10 O23 1.228(2) . ? C10 C11 1.512(2) . ? C11 C12 1.538(2) . ? C12 C13 1.554(2) . ? C13 C14 1.530(2) . ? C13 C18 1.544(2) . ? C14 C15 1.399(2) . ? C14 C19 1.403(2) . ? C15 C22 1.401(2) . ? C15 C16 1.514(2) . ? C16 C17 1.517(3) . ? C17 C18 1.520(2) . ? C19 C20 1.385(2) . ? C20 C21 1.392(3) . ? C21 C22 1.378(3) . ? 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 C1 C6 120.26(15) . . ? C2 C1 C9 128.74(15) . . ? C6 C1 C9 110.89(14) . . ? C1 C2 C3 118.76(17) . . ? C4 C3 C2 120.86(17) . . ? C5 C4 C3 120.44(16) . . ? C4 C5 C6 118.72(17) . . ? C1 C6 C5 120.94(16) . . ? C1 C6 C7 111.08(14) . . ? C5 C6 C7 127.97(16) . . ? N8 C7 C6 101.95(13) . . ? C10 N8 C7 124.06(14) . . ? C10 N8 C9 120.71(13) . . ? C7 N8 C9 114.22(13) . . ? N8 C9 C1 101.54(12) . . ? N8 C9 C13 113.30(13) . . ? C1 C9 C13 120.02(13) . . ? O23 C10 N8 122.82(15) . . ? O23 C10 C11 125.04(15) . . ? N8 C10 C11 112.05(14) . . ? C10 C11 C12 109.23(14) . . ? C11 C12 C13 113.01(13) . . ? C14 C13 C18 111.84(13) . . ? C14 C13 C12 109.66(12) . . ? C18 C13 C12 109.40(13) . . ? C14 C13 C9 112.66(12) . . ? C18 C13 C9 105.69(12) . . ? C12 C13 C9 107.41(12) . . ? C15 C14 C19 118.65(15) . . ? C15 C14 C13 122.20(14) . . ? C19 C14 C13 119.12(14) . . ? C14 C15 C22 119.18(15) . . ? C14 C15 C16 122.03(15) . . ? C22 C15 C16 118.78(15) . . ? C15 C16 C17 111.54(14) . . ? C16 C17 C18 108.95(14) . . ? C17 C18 C13 113.01(13) . . ? C20 C19 C14 121.57(16) . . ? C19 C20 C21 119.47(17) . . ? C22 C21 C20 119.62(16) . . ? C21 C22 C15 121.51(16) . . ? _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 26.77 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 0.265 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.047