data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Peter Langer' _publ_contact_author_address ; Institut fur Chemie, Abteilung fur Organische Chemie Universitat Rostock Albert-Einstein-Strasse 3a Rostock 18051 GERMANY ; _publ_contact_author_email PETER.LANGER@UNI-ROSTOCK.DE _publ_section_title ; Synthesis of Azoxabicyclo[3.3.1]nonanones based on Diastereoselective Reactions of 1,1-Bis(trimethylsilyloxy)ketene Acetals with Isoquinolines and Quinolines ; loop_ _publ_author_name 'Peter Langer' 'Christine Fischer' 'Helmar Gorls' 'Dirk Michalik' 'Helmut Reinke' 'Sven Rotzoll' ; A.Schmidt ; 'Ehsan Ullah' data_FO2669 _database_code_depnum_ccdc_archive 'CCDC 680062' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 N O4' _chemical_formula_sum 'C16 H19 N O4' _chemical_formula_weight 289.32 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 P2(1)/n _symmetry_space_group_name_Hall -P2yn 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 5.1502(3) _cell_length_b 11.2491(9) _cell_length_c 26.050(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.408(5) _cell_angle_gamma 90.00 _cell_volume 1509.15(19) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8536 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.47 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.092 _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 183(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 KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8536 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3396 _reflns_number_gt 2016 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _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^)+(0.0640P)^2^+0.3701P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom/difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3396 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1210 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1518 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 O1 O 0.1975(3) -0.25651(15) 0.14614(6) 0.0473(5) Uani 1 1 d . . . O2 O 0.3959(4) -0.13477(14) 0.09079(6) 0.0525(5) Uani 1 1 d . . . O3 O -0.1561(3) 0.02610(17) 0.06128(6) 0.0476(5) Uani 1 1 d . . . O4 O 0.2160(3) 0.08471(15) 0.02695(6) 0.0441(4) Uani 1 1 d . . . N1 N 0.1955(3) -0.05429(15) 0.15825(6) 0.0303(4) Uani 1 1 d . . . C1 C 0.3179(4) 0.06052(19) 0.14449(8) 0.0306(5) Uani 1 1 d . . . H1A H 0.4710 0.0436 0.1223 0.037 Uiso 1 1 calc R . . C2 C 0.4129(4) 0.1227(2) 0.19204(8) 0.0335(5) Uani 1 1 d . . . H2A H 0.5552 0.1761 0.1897 0.040 Uiso 1 1 calc R . . C3 C 0.3025(4) 0.1046(2) 0.23717(8) 0.0343(5) Uani 1 1 d . . . H3A H 0.3629 0.1472 0.2664 0.041 Uiso 1 1 calc R . . C4 C 0.0901(4) 0.0203(2) 0.24262(8) 0.0329(5) Uani 1 1 d . . . C5 C -0.0595(4) 0.0157(2) 0.28707(8) 0.0395(6) Uani 1 1 d . . . H5A H -0.0223 0.0685 0.3146 0.047 Uiso 1 1 calc R . . C6 C -0.2607(5) -0.0646(2) 0.29147(10) 0.0460(6) Uani 1 1 d . . . H6A H -0.3600 -0.0676 0.3220 0.055 Uiso 1 1 calc R . . C7 C -0.3173(4) -0.1409(2) 0.25111(9) 0.0414(6) Uani 1 1 d . . . H7A H -0.4573 -0.1954 0.2539 0.050 Uiso 1 1 calc R . . C8 C -0.1716(4) -0.1381(2) 0.20688(9) 0.0362(5) Uani 1 1 d . . . H8A H -0.2119 -0.1905 0.1793 0.043 Uiso 1 1 calc R . . C9 C 0.0340(4) -0.05874(19) 0.20255(8) 0.0312(5) Uani 1 1 d . . . C10 C 0.2581(4) -0.1568(2) 0.13295(8) 0.0365(6) Uani 1 1 d . . . C11 C 0.4742(8) -0.2388(3) 0.06258(13) 0.0890(13) Uani 1 1 d . . . H11A H 0.5497 -0.2147 0.0298 0.134 Uiso 1 1 calc R . . H11B H 0.3225 -0.2894 0.0562 0.134 Uiso 1 1 calc R . . H11C H 0.6035 -0.2832 0.0826 0.134 Uiso 1 1 calc R . . C12 C 0.1260(4) 0.14090(19) 0.11366(8) 0.0314(5) Uani 1 1 d . . . H12A H -0.0386 0.1485 0.1335 0.038 Uiso 1 1 calc R . . C13 C 0.0657(4) 0.08138(19) 0.06311(8) 0.0309(5) Uani 1 1 d . . . C14 C 0.2350(5) 0.2653(2) 0.10409(8) 0.0393(6) Uani 1 1 d . . . H14A H 0.2737 0.3031 0.1376 0.047 Uiso 1 1 calc R . . H14B H 0.4007 0.2578 0.0853 0.047 Uiso 1 1 calc R . . C15 C 0.0535(6) 0.3461(2) 0.07364(9) 0.0507(7) Uani 1 1 d . . . H15A H 0.0236 0.3114 0.0392 0.061 Uiso 1 1 calc R . . H15B H -0.1160 0.3504 0.0912 0.061 Uiso 1 1 calc R . . C16 C 0.1616(7) 0.4708(3) 0.06771(12) 0.0754(10) Uani 1 1 d . . . H16A H 0.0372 0.5199 0.0485 0.113 Uiso 1 1 calc R . . H16B H 0.3260 0.4674 0.0491 0.113 Uiso 1 1 calc R . . H16C H 0.1915 0.5057 0.1017 0.113 Uiso 1 1 calc R . . H1O3 H -0.176(6) -0.012(3) 0.0283(12) 0.078(10) Uiso 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 0.0714(12) 0.0287(10) 0.0420(10) 0.0008(8) 0.0157(8) -0.0054(8) O2 0.0853(13) 0.0304(9) 0.0422(10) -0.0094(8) 0.0282(9) -0.0152(9) O3 0.0386(9) 0.0681(12) 0.0363(9) -0.0164(9) 0.0067(7) -0.0213(9) O4 0.0459(9) 0.0565(11) 0.0300(8) -0.0086(8) 0.0082(7) -0.0198(8) N1 0.0372(10) 0.0260(10) 0.0278(9) -0.0011(8) 0.0021(8) -0.0046(8) C1 0.0329(11) 0.0289(12) 0.0301(11) -0.0024(9) 0.0029(9) -0.0056(9) C2 0.0339(11) 0.0307(13) 0.0358(12) -0.0048(10) -0.0030(9) -0.0012(10) C3 0.0362(12) 0.0335(13) 0.0331(12) -0.0067(10) -0.0060(9) 0.0029(10) C4 0.0338(12) 0.0348(13) 0.0301(12) 0.0016(10) -0.0017(9) 0.0078(10) C5 0.0439(13) 0.0443(15) 0.0304(12) 0.0043(11) 0.0013(10) 0.0084(12) C6 0.0469(14) 0.0512(17) 0.0400(14) 0.0149(12) 0.0111(11) 0.0105(12) C7 0.0355(12) 0.0381(15) 0.0506(15) 0.0142(12) 0.0048(11) 0.0028(10) C8 0.0363(12) 0.0306(13) 0.0417(13) 0.0052(10) -0.0014(10) -0.0004(10) C9 0.0331(11) 0.0300(13) 0.0306(11) 0.0033(9) 0.0002(9) 0.0039(9) C10 0.0467(14) 0.0338(14) 0.0290(12) -0.0002(10) 0.0035(10) -0.0057(11) C11 0.153(3) 0.0412(18) 0.073(2) -0.0212(16) 0.069(2) -0.022(2) C12 0.0354(11) 0.0327(13) 0.0262(11) -0.0010(9) 0.0016(9) -0.0056(9) C13 0.0338(11) 0.0289(12) 0.0301(11) 0.0009(10) 0.0022(9) -0.0045(10) C14 0.0540(14) 0.0323(13) 0.0315(12) -0.0004(10) -0.0017(10) -0.0081(11) C15 0.0762(18) 0.0374(15) 0.0384(14) 0.0008(11) -0.0124(13) -0.0058(13) C16 0.124(3) 0.0372(17) 0.0650(19) 0.0134(14) -0.0185(19) -0.0173(18) _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 C10 1.215(3) . ? O2 C10 1.335(3) . ? O2 C11 1.441(3) . ? O3 C13 1.301(3) . ? O4 C13 1.224(3) . ? N1 C10 1.368(3) . ? N1 C9 1.428(3) . ? N1 C1 1.482(3) . ? C1 C2 1.501(3) . ? C1 C12 1.558(3) . ? C2 C3 1.325(3) . ? C3 C4 1.455(3) . ? C4 C5 1.396(3) . ? C4 C9 1.400(3) . ? C5 C6 1.380(3) . ? C6 C7 1.386(4) . ? C7 C8 1.380(3) . ? C8 C9 1.390(3) . ? C12 C13 1.508(3) . ? C12 C14 1.529(3) . ? C14 C15 1.523(3) . ? C15 C16 1.518(4) . ? 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 C11 114.91(19) . . ? C10 N1 C9 120.04(18) . . ? C10 N1 C1 121.05(17) . . ? C9 N1 C1 118.49(17) . . ? N1 C1 C2 110.05(17) . . ? N1 C1 C12 111.16(16) . . ? C2 C1 C12 110.91(17) . . ? C3 C2 C1 121.4(2) . . ? C2 C3 C4 120.9(2) . . ? C5 C4 C9 118.8(2) . . ? C5 C4 C3 121.7(2) . . ? C9 C4 C3 119.50(19) . . ? C6 C5 C4 120.8(2) . . ? C5 C6 C7 119.7(2) . . ? C8 C7 C6 120.4(2) . . ? C7 C8 C9 120.1(2) . . ? C8 C9 C4 120.1(2) . . ? C8 C9 N1 122.44(19) . . ? C4 C9 N1 117.50(19) . . ? O1 C10 O2 122.9(2) . . ? O1 C10 N1 125.5(2) . . ? O2 C10 N1 111.64(19) . . ? C13 C12 C14 109.74(17) . . ? C13 C12 C1 108.57(17) . . ? C14 C12 C1 112.52(17) . . ? O4 C13 O3 123.11(19) . . ? O4 C13 C12 122.08(19) . . ? O3 C13 C12 114.81(18) . . ? C15 C14 C12 113.99(19) . . ? C16 C15 C14 112.4(2) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.181 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.050