# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Richard Hsung' _publ_contact_author_name 'Richard Hsung' _publ_contact_author_email RHSUNG@WISC.EDU _publ_section_title ; Synthesis of Amido-Spiro [2.2] Pentanes via Simmons-Smith Cyclopropanation of Allenamides. ; # Attachment 'amino-spiro[2.2]pentanes_07113A.CIF' data_07113a _database_code_depnum_ccdc_archive 'CCDC 729826' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 07113a _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 N O2' _chemical_formula_sum 'C17 H15 N O2' _chemical_formula_weight 265.30 _chemical_absolute_configuration rm 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 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.0167(5) _cell_length_b 10.2379(9) _cell_length_c 22.355(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1377.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2381 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 26.68 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9793 _exptl_absorpt_correction_T_max 0.9892 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details 'T. Lu / Prof. R. Hsung - U. Wisconsin' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12782 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.14 _reflns_number_total 1790 _reflns_number_gt 1431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0388P)^2^+0.1181P] 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 2.5(17) _refine_ls_number_reflns 1790 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0803 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 C1 C 0.3698(3) 0.32523(17) 0.08091(8) 0.0325(4) Uani 1 1 d . . . C2 C 0.1847(4) 0.40487(18) 0.07215(8) 0.0388(5) Uani 1 1 d . . . H2A H 0.0654 0.4022 0.1000 0.047 Uiso 1 1 calc R . . C3 C 0.1726(4) 0.4881(2) 0.02323(9) 0.0444(5) Uani 1 1 d . . . H3A H 0.0449 0.5413 0.0176 0.053 Uiso 1 1 calc R . . C4 C 0.3452(4) 0.4939(2) -0.01727(9) 0.0466(5) Uani 1 1 d . . . H4A H 0.3353 0.5496 -0.0512 0.056 Uiso 1 1 calc R . . C5 C 0.5317(4) 0.4188(2) -0.00836(9) 0.0461(5) Uani 1 1 d . . . H5A H 0.6526 0.4244 -0.0356 0.055 Uiso 1 1 calc R . . C6 C 0.5440(4) 0.3350(2) 0.04025(8) 0.0390(5) Uani 1 1 d . . . H6A H 0.6735 0.2833 0.0459 0.047 Uiso 1 1 calc R . . C7 C 0.3843(3) 0.22775(18) 0.12943(8) 0.0333(4) Uani 1 1 d . . . H7A H 0.5181 0.1791 0.1330 0.040 Uiso 1 1 calc R . . C8 C 0.2232(3) 0.20355(17) 0.16837(8) 0.0324(4) Uani 1 1 d . . . H8A H 0.0933 0.2560 0.1659 0.039 Uiso 1 1 calc R . . N1 N 0.2281(3) 0.10760(14) 0.21267(6) 0.0326(4) Uani 1 1 d . . . C9 C 0.0558(3) 0.09373(19) 0.25180(9) 0.0373(5) Uani 1 1 d . . . O1 O -0.1156(2) 0.15427(15) 0.25243(6) 0.0475(4) Uani 1 1 d . . . O2 O 0.1033(3) -0.00127(14) 0.29151(6) 0.0464(4) Uani 1 1 d . . . C10 C 0.3291(4) -0.0442(2) 0.28382(8) 0.0463(5) Uani 1 1 d . . . H10A H 0.3354 -0.1406 0.2807 0.056 Uiso 1 1 calc R . . H10B H 0.4214 -0.0165 0.3182 0.056 Uiso 1 1 calc R . . C11 C 0.4136(3) 0.01978(18) 0.22542(8) 0.0345(4) Uani 1 1 d . . . H11A H 0.5507 0.0719 0.2338 0.041 Uiso 1 1 calc R . . C12 C 0.4607(3) -0.07955(18) 0.17696(8) 0.0327(4) Uani 1 1 d . . . C13 C 0.6647(3) -0.14292(19) 0.17715(8) 0.0378(5) Uani 1 1 d . . . H13A H 0.7740 -0.1190 0.2058 0.045 Uiso 1 1 calc R . . C14 C 0.7107(4) -0.2405(2) 0.13613(9) 0.0422(5) Uani 1 1 d . . . H14A H 0.8508 -0.2833 0.1369 0.051 Uiso 1 1 calc R . . C15 C 0.5535(4) -0.2758(2) 0.09411(9) 0.0468(5) Uani 1 1 d . . . H15A H 0.5846 -0.3430 0.0660 0.056 Uiso 1 1 calc R . . C16 C 0.3506(4) -0.2125(2) 0.09324(9) 0.0460(5) Uani 1 1 d . . . H16A H 0.2424 -0.2359 0.0642 0.055 Uiso 1 1 calc R . . C17 C 0.3038(3) -0.11494(18) 0.13446(8) 0.0377(5) Uani 1 1 d . . . H17A H 0.1637 -0.0722 0.1336 0.045 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 C1 0.0423(10) 0.0244(9) 0.0309(9) -0.0045(7) -0.0018(8) -0.0030(8) C2 0.0481(12) 0.0332(10) 0.0351(9) 0.0007(9) 0.0016(9) 0.0020(10) C3 0.0571(13) 0.0325(11) 0.0437(10) 0.0021(9) -0.0062(10) 0.0037(10) C4 0.0744(15) 0.0305(10) 0.0350(9) 0.0030(9) -0.0008(11) -0.0011(12) C5 0.0648(14) 0.0358(11) 0.0376(11) -0.0014(9) 0.0123(10) -0.0022(11) C6 0.0472(11) 0.0290(10) 0.0408(10) -0.0032(9) 0.0040(9) 0.0013(9) C7 0.0368(10) 0.0277(9) 0.0356(9) -0.0022(8) -0.0035(8) 0.0005(9) C8 0.0377(10) 0.0251(9) 0.0344(9) 0.0009(8) -0.0067(8) 0.0015(8) N1 0.0364(8) 0.0287(8) 0.0326(7) 0.0018(7) -0.0029(7) -0.0005(7) C9 0.0433(12) 0.0304(10) 0.0380(10) -0.0015(9) -0.0029(9) -0.0112(9) O1 0.0365(7) 0.0485(9) 0.0577(9) -0.0016(7) 0.0036(7) -0.0040(8) O2 0.0599(9) 0.0384(8) 0.0409(7) 0.0058(7) 0.0054(7) -0.0052(8) C10 0.0633(14) 0.0406(12) 0.0349(10) 0.0030(9) -0.0062(10) 0.0068(11) C11 0.0363(10) 0.0296(10) 0.0376(9) 0.0014(8) -0.0104(8) -0.0019(9) C12 0.0393(11) 0.0253(9) 0.0334(9) 0.0056(8) -0.0033(8) -0.0041(8) C13 0.0391(11) 0.0356(10) 0.0387(9) 0.0076(9) -0.0059(8) -0.0009(9) C14 0.0477(11) 0.0335(11) 0.0455(10) 0.0066(9) 0.0035(10) 0.0042(10) C15 0.0652(14) 0.0330(11) 0.0423(11) -0.0017(10) 0.0043(11) 0.0028(11) C16 0.0570(13) 0.0386(12) 0.0424(10) -0.0038(10) -0.0108(11) -0.0059(11) C17 0.0391(10) 0.0321(10) 0.0419(10) 0.0025(9) -0.0078(9) -0.0013(9) _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 C6 1.391(3) . ? C1 C2 1.394(3) . ? C1 C7 1.476(2) . ? C2 C3 1.388(3) . ? C2 H2A 0.9500 . ? C3 C4 1.379(3) . ? C3 H3A 0.9500 . ? C4 C5 1.375(3) . ? C4 H4A 0.9500 . ? C5 C6 1.387(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.326(3) . ? C7 H7A 0.9500 . ? C8 N1 1.395(2) . ? C8 H8A 0.9500 . ? N1 C9 1.364(2) . ? N1 C11 1.461(2) . ? C9 O1 1.203(2) . ? C9 O2 1.347(2) . ? O2 C10 1.438(3) . ? C10 C11 1.547(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.513(3) . ? C11 H11A 1.0000 . ? C12 C17 1.387(3) . ? C12 C13 1.388(3) . ? C13 C14 1.384(3) . ? C13 H13A 0.9500 . ? C14 C15 1.381(3) . ? C14 H14A 0.9500 . ? C15 C16 1.383(3) . ? C15 H15A 0.9500 . ? C16 C17 1.388(3) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? 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 C1 C2 117.93(17) . . ? C6 C1 C7 118.94(17) . . ? C2 C1 C7 123.07(17) . . ? C3 C2 C1 120.75(19) . . ? C3 C2 H2A 119.6 . . ? C1 C2 H2A 119.6 . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C5 C4 C3 119.69(18) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 119.9 . . ? C5 C6 C1 121.1(2) . . ? C5 C6 H6A 119.5 . . ? C1 C6 H6A 119.5 . . ? C8 C7 C1 124.42(18) . . ? C8 C7 H7A 117.8 . . ? C1 C7 H7A 117.8 . . ? C7 C8 N1 125.59(18) . . ? C7 C8 H8A 117.2 . . ? N1 C8 H8A 117.2 . . ? C9 N1 C8 120.83(16) . . ? C9 N1 C11 113.04(14) . . ? C8 N1 C11 126.01(16) . . ? O1 C9 O2 123.07(18) . . ? O1 C9 N1 127.25(18) . . ? O2 C9 N1 109.68(17) . . ? C9 O2 C10 110.00(16) . . ? O2 C10 C11 106.37(16) . . ? O2 C10 H10A 110.5 . . ? C11 C10 H10A 110.5 . . ? O2 C10 H10B 110.5 . . ? C11 C10 H10B 110.5 . . ? H10A C10 H10B 108.6 . . ? N1 C11 C12 114.66(15) . . ? N1 C11 C10 100.03(15) . . ? C12 C11 C10 112.41(15) . . ? N1 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? C10 C11 H11A 109.8 . . ? C17 C12 C13 118.79(17) . . ? C17 C12 C11 122.58(17) . . ? C13 C12 C11 118.53(17) . . ? C14 C13 C12 120.80(18) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C15 C14 C13 120.2(2) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C14 C15 C16 119.5(2) . . ? C14 C15 H15A 120.3 . . ? C16 C15 H15A 120.3 . . ? C15 C16 C17 120.46(19) . . ? C15 C16 H16A 119.8 . . ? C17 C16 H16A 119.8 . . ? C12 C17 C16 120.32(19) . . ? C12 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? 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 C1 C2 C3 2.0(3) . . . . ? C7 C1 C2 C3 -175.18(17) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C2 C3 C4 C5 -1.3(3) . . . . ? C3 C4 C5 C6 1.7(3) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? C2 C1 C6 C5 -1.6(3) . . . . ? C7 C1 C6 C5 175.68(17) . . . . ? C6 C1 C7 C8 -175.40(18) . . . . ? C2 C1 C7 C8 1.7(3) . . . . ? C1 C7 C8 N1 176.56(16) . . . . ? C7 C8 N1 C9 177.81(17) . . . . ? C7 C8 N1 C11 2.2(3) . . . . ? C8 N1 C9 O1 2.7(3) . . . . ? C11 N1 C9 O1 178.89(18) . . . . ? C8 N1 C9 O2 -177.54(15) . . . . ? C11 N1 C9 O2 -1.4(2) . . . . ? O1 C9 O2 C10 -173.13(17) . . . . ? N1 C9 O2 C10 7.1(2) . . . . ? C9 O2 C10 C11 -9.7(2) . . . . ? C9 N1 C11 C12 116.15(18) . . . . ? C8 N1 C11 C12 -67.9(2) . . . . ? C9 N1 C11 C10 -4.33(19) . . . . ? C8 N1 C11 C10 171.60(16) . . . . ? O2 C10 C11 N1 8.09(19) . . . . ? O2 C10 C11 C12 -114.00(18) . . . . ? N1 C11 C12 C17 -20.5(2) . . . . ? C10 C11 C12 C17 92.8(2) . . . . ? N1 C11 C12 C13 163.14(16) . . . . ? C10 C11 C12 C13 -83.5(2) . . . . ? C17 C12 C13 C14 -0.6(3) . . . . ? C11 C12 C13 C14 175.88(17) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? C14 C15 C16 C17 -0.5(3) . . . . ? C13 C12 C17 C16 0.3(3) . . . . ? C11 C12 C17 C16 -175.95(18) . . . . ? C15 C16 C17 C12 0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.123 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.030 # Attachment 'amino-spiro[2.2]pentanes_07114A.CIF' data_07114a _database_code_depnum_ccdc_archive 'CCDC 729827' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 07114a _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 N O2' _chemical_formula_sum 'C17 H15 N O2' _chemical_formula_weight 265.30 _chemical_absolute_configuration rm 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 'C2 ' 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' _cell_length_a 30.294(8) _cell_length_b 6.4077(17) _cell_length_c 7.0525(19) _cell_angle_alpha 90.00 _cell_angle_beta 100.238(4) _cell_angle_gamma 90.00 _cell_volume 1347.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2634 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 26.23 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9583 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details 'T. Lu / Prof. R. Hsung - U. Wisconsin' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5729 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 26.34 _reflns_number_total 1492 _reflns_number_gt 1206 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0539P)^2^+0.0303P] 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 -1.6(18) _refine_ls_number_reflns 1492 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0868 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.054 _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 C1 C 0.89605(8) 0.4916(4) 0.7270(3) 0.0245(6) Uani 1 1 d . . . C2 C 0.94182(9) 0.5362(5) 0.7700(4) 0.0315(6) Uani 1 1 d . . . H2A H 0.9515 0.6699 0.8190 0.038 Uiso 1 1 calc R . . C3 C 0.97339(9) 0.3886(5) 0.7424(4) 0.0366(7) Uani 1 1 d . . . H3A H 1.0044 0.4217 0.7713 0.044 Uiso 1 1 calc R . . C4 C 0.95970(10) 0.1917(5) 0.6723(4) 0.0363(7) Uani 1 1 d . . . H4A H 0.9813 0.0910 0.6508 0.044 Uiso 1 1 calc R . . C5 C 0.91434(9) 0.1432(4) 0.6338(4) 0.0311(6) Uani 1 1 d . . . H5A H 0.9049 0.0081 0.5879 0.037 Uiso 1 1 calc R . . C6 C 0.88269(9) 0.2918(4) 0.6622(4) 0.0266(6) Uani 1 1 d . . . H6A H 0.8517 0.2569 0.6374 0.032 Uiso 1 1 calc R . . C7 C 0.86345(9) 0.6543(4) 0.7584(4) 0.0287(6) Uani 1 1 d . . . H7A H 0.8723 0.7361 0.8711 0.034 Uiso 1 1 calc R . . C8 C 0.82359(9) 0.7053(4) 0.6549(4) 0.0272(6) Uani 1 1 d . . . H8A H 0.8067 0.8043 0.7122 0.033 Uiso 1 1 calc R . . N1 N 0.80342(6) 0.6317(3) 0.4722(3) 0.0247(5) Uani 1 1 d . . . C9 C 0.75809(9) 0.6448(4) 0.4134(4) 0.0277(6) Uani 1 1 d . . . O1 O 0.73060(6) 0.6937(3) 0.5110(3) 0.0386(5) Uani 1 1 d . . . O2 O 0.74709(6) 0.5956(3) 0.2241(3) 0.0334(5) Uani 1 1 d . . . C10 C 0.78617(9) 0.5157(5) 0.1579(4) 0.0334(6) Uani 1 1 d . . . H10A H 0.7896 0.5833 0.0352 0.040 Uiso 1 1 calc R . . H10B H 0.7835 0.3631 0.1369 0.040 Uiso 1 1 calc R . . C11 C 0.82666(8) 0.5660(4) 0.3165(3) 0.0247(6) Uani 1 1 d . . . H11A H 0.8440 0.4353 0.3552 0.030 Uiso 1 1 calc R . . C12 C 0.85800(8) 0.7322(4) 0.2631(4) 0.0248(6) Uani 1 1 d . . . C13 C 0.84160(9) 0.9252(4) 0.1920(4) 0.0292(6) Uani 1 1 d . . . H13A H 0.8108 0.9578 0.1856 0.035 Uiso 1 1 calc R . . C14 C 0.87013(10) 1.0708(4) 0.1300(4) 0.0336(7) Uani 1 1 d . . . H14A H 0.8586 1.2009 0.0791 0.040 Uiso 1 1 calc R . . C15 C 0.91515(10) 1.0264(5) 0.1424(4) 0.0355(7) Uani 1 1 d . . . H15A H 0.9345 1.1262 0.1006 0.043 Uiso 1 1 calc R . . C16 C 0.93207(9) 0.8365(5) 0.2157(4) 0.0334(7) Uani 1 1 d . . . H16A H 0.9631 0.8069 0.2258 0.040 Uiso 1 1 calc R . . C17 C 0.90359(8) 0.6888(5) 0.2749(4) 0.0290(6) Uani 1 1 d . . . H17A H 0.9152 0.5579 0.3235 0.035 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 C1 0.0235(15) 0.0286(14) 0.0214(12) 0.0008(11) 0.0036(11) 0.0004(11) C2 0.0271(15) 0.0334(15) 0.0325(14) -0.0033(12) 0.0010(12) -0.0004(13) C3 0.0234(15) 0.0448(18) 0.0410(16) -0.0012(14) 0.0036(13) 0.0007(14) C4 0.0340(17) 0.0394(16) 0.0372(15) 0.0020(13) 0.0105(13) 0.0117(14) C5 0.0368(16) 0.0267(15) 0.0290(14) 0.0016(12) 0.0039(12) 0.0050(13) C6 0.0230(14) 0.0321(14) 0.0240(14) 0.0003(11) 0.0024(11) -0.0027(12) C7 0.0326(15) 0.0286(15) 0.0263(13) -0.0084(12) 0.0091(12) -0.0004(13) C8 0.0301(15) 0.0242(12) 0.0298(14) -0.0016(11) 0.0122(12) 0.0044(12) N1 0.0204(11) 0.0247(11) 0.0298(11) -0.0014(9) 0.0071(9) -0.0001(9) C9 0.0251(15) 0.0175(13) 0.0402(15) 0.0014(12) 0.0053(12) -0.0004(11) O1 0.0255(10) 0.0323(11) 0.0601(13) -0.0062(10) 0.0132(10) 0.0005(8) O2 0.0246(11) 0.0317(11) 0.0413(11) 0.0007(9) -0.0017(8) -0.0006(8) C10 0.0321(16) 0.0359(15) 0.0324(14) -0.0019(13) 0.0062(12) -0.0059(14) C11 0.0244(14) 0.0244(13) 0.0256(12) -0.0007(11) 0.0048(11) 0.0014(11) C12 0.0230(14) 0.0273(15) 0.0237(13) -0.0058(10) 0.0032(11) -0.0039(11) C13 0.0283(15) 0.0283(14) 0.0325(14) -0.0018(12) 0.0101(12) 0.0018(12) C14 0.0462(18) 0.0254(14) 0.0310(14) -0.0030(11) 0.0118(13) -0.0025(13) C15 0.0411(18) 0.0362(17) 0.0321(15) -0.0075(13) 0.0142(13) -0.0150(14) C16 0.0246(15) 0.0424(18) 0.0339(15) -0.0064(13) 0.0068(12) -0.0081(13) C17 0.0260(14) 0.0328(14) 0.0276(13) -0.0032(11) 0.0033(11) 0.0016(12) _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 C6 1.395(4) . ? C1 C2 1.395(4) . ? C1 C7 1.479(4) . ? C2 C3 1.383(4) . ? C2 H2A 0.9500 . ? C3 C4 1.391(4) . ? C3 H3A 0.9500 . ? C4 C5 1.388(4) . ? C4 H4A 0.9500 . ? C5 C6 1.391(4) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.336(4) . ? C7 H7A 0.9500 . ? C8 N1 1.406(3) . ? C8 H8A 0.9500 . ? N1 C9 1.365(3) . ? N1 C11 1.467(3) . ? C9 O1 1.212(3) . ? C9 O2 1.354(3) . ? O2 C10 1.441(3) . ? C10 C11 1.540(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(3) . ? C11 H11A 1.0000 . ? C12 C13 1.393(4) . ? C12 C17 1.397(4) . ? C13 C14 1.393(4) . ? C13 H13A 0.9500 . ? C14 C15 1.381(4) . ? C14 H14A 0.9500 . ? C15 C16 1.384(4) . ? C15 H15A 0.9500 . ? C16 C17 1.394(4) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? 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 C1 C2 118.6(2) . . ? C6 C1 C7 122.2(2) . . ? C2 C1 C7 119.2(2) . . ? C3 C2 C1 121.0(3) . . ? C3 C2 H2A 119.5 . . ? C1 C2 H2A 119.5 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 119.7(2) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 119.9 . . ? C5 C6 C1 120.5(2) . . ? C5 C6 H6A 119.7 . . ? C1 C6 H6A 119.7 . . ? C8 C7 C1 130.8(2) . . ? C8 C7 H7A 114.6 . . ? C1 C7 H7A 114.6 . . ? C7 C8 N1 128.5(2) . . ? C7 C8 H8A 115.8 . . ? N1 C8 H8A 115.8 . . ? C9 N1 C8 120.5(2) . . ? C9 N1 C11 112.4(2) . . ? C8 N1 C11 126.4(2) . . ? O1 C9 O2 123.1(2) . . ? O1 C9 N1 126.8(2) . . ? O2 C9 N1 110.1(2) . . ? C9 O2 C10 109.26(18) . . ? O2 C10 C11 106.5(2) . . ? O2 C10 H10A 110.4 . . ? C11 C10 H10A 110.4 . . ? O2 C10 H10B 110.4 . . ? C11 C10 H10B 110.4 . . ? H10A C10 H10B 108.6 . . ? N1 C11 C12 112.9(2) . . ? N1 C11 C10 100.22(19) . . ? C12 C11 C10 114.8(2) . . ? N1 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? C13 C12 C17 118.9(2) . . ? C13 C12 C11 120.9(2) . . ? C17 C12 C11 120.1(2) . . ? C12 C13 C14 120.4(2) . . ? C12 C13 H13A 119.8 . . ? C14 C13 H13A 119.8 . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C14 C15 C16 120.0(3) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C15 C16 C17 120.1(3) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C16 C17 C12 120.3(3) . . ? C16 C17 H17A 119.8 . . ? C12 C17 H17A 119.8 . . ? 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 C1 C2 C3 2.4(4) . . . . ? C7 C1 C2 C3 -179.9(2) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C3 C4 C5 C6 1.0(4) . . . . ? C4 C5 C6 C1 0.9(4) . . . . ? C2 C1 C6 C5 -2.6(4) . . . . ? C7 C1 C6 C5 179.8(2) . . . . ? C6 C1 C7 C8 -41.0(4) . . . . ? C2 C1 C7 C8 141.5(3) . . . . ? C1 C7 C8 N1 -7.9(5) . . . . ? C7 C8 N1 C9 158.7(3) . . . . ? C7 C8 N1 C11 -31.4(4) . . . . ? C8 N1 C9 O1 -9.2(4) . . . . ? C11 N1 C9 O1 179.5(3) . . . . ? C8 N1 C9 O2 170.5(2) . . . . ? C11 N1 C9 O2 -0.8(3) . . . . ? O1 C9 O2 C10 -171.6(2) . . . . ? N1 C9 O2 C10 8.7(3) . . . . ? C9 O2 C10 C11 -12.7(3) . . . . ? C9 N1 C11 C12 116.0(2) . . . . ? C8 N1 C11 C12 -54.7(3) . . . . ? C9 N1 C11 C10 -6.6(3) . . . . ? C8 N1 C11 C10 -177.3(2) . . . . ? O2 C10 C11 N1 11.2(2) . . . . ? O2 C10 C11 C12 -110.0(2) . . . . ? N1 C11 C12 C13 -61.9(3) . . . . ? C10 C11 C12 C13 52.1(3) . . . . ? N1 C11 C12 C17 121.7(3) . . . . ? C10 C11 C12 C17 -124.3(3) . . . . ? C17 C12 C13 C14 1.3(4) . . . . ? C11 C12 C13 C14 -175.2(2) . . . . ? C12 C13 C14 C15 -1.3(4) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C14 C15 C16 C17 0.8(4) . . . . ? C15 C16 C17 C12 -0.9(4) . . . . ? C13 C12 C17 C16 -0.2(4) . . . . ? C11 C12 C17 C16 176.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.34 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.148 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.041 # Attachment 'amino-spiro[2.2]pentanes_08084.cif' data_08084 _database_code_depnum_ccdc_archive 'CCDC 729828' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 08084 _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 N O2' _chemical_formula_sum 'C14 H15 N O2' _chemical_formula_weight 229.27 _chemical_absolute_configuration rm 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.2295(4) _cell_length_b 11.8164(7) _cell_length_c 12.8744(8) _cell_angle_alpha 84.5470(10) _cell_angle_beta 86.5820(10) _cell_angle_gamma 76.4120(10) _cell_volume 916.31(10) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4023 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 25.58 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 366 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9595 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10128 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3730 _reflns_number_gt 3233 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _computing_publication_material 'Bruker 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^)+(0.0398P)^2^+0.0858P] 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), 3730 Friedel Pairs, Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 3730 _refine_ls_number_parameters 460 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0793 _refine_ls_wR_factor_gt 0.0732 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.037 _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 -0.3899(3) 0.92079(17) 0.01639(13) 0.0469(4) Uani 1 1 d . . . O2 O -0.0400(3) 0.82138(15) -0.01128(12) 0.0415(4) Uani 1 1 d . . . N1 N -0.0952(3) 0.97002(16) 0.08725(14) 0.0318(4) Uani 1 1 d . . . C1 C -0.1955(4) 0.9071(2) 0.03145(17) 0.0347(5) Uani 1 1 d . . . C2 C 0.1777(4) 0.8354(2) 0.01016(18) 0.0386(5) Uani 1 1 d . . . H2A H 0.2447 0.8717 -0.0522 0.046 Uiso 1 1 calc R . . H2B H 0.2765 0.7590 0.0312 0.046 Uiso 1 1 calc R . . C3 C 0.1389(3) 0.91572(19) 0.10004(16) 0.0311(5) Uani 1 1 d . . . H3A H 0.2279 0.9762 0.0859 0.037 Uiso 1 1 calc R . . C4 C 0.1890(3) 0.85197(18) 0.20672(16) 0.0301(5) Uani 1 1 d . . . C5 C 0.0589(4) 0.7800(2) 0.25487(19) 0.0386(5) Uani 1 1 d . . . H5A H -0.0693 0.7727 0.2221 0.046 Uiso 1 1 calc R . . C6 C 0.1144(4) 0.7189(2) 0.3500(2) 0.0438(6) Uani 1 1 d . . . H6A H 0.0245 0.6697 0.3821 0.053 Uiso 1 1 calc R . . C7 C 0.2990(4) 0.7289(2) 0.39859(19) 0.0433(6) Uani 1 1 d . . . H7A H 0.3380 0.6857 0.4635 0.052 Uiso 1 1 calc R . . C8 C 0.4269(4) 0.8017(2) 0.35282(19) 0.0447(6) Uani 1 1 d . . . H8A H 0.5530 0.8100 0.3868 0.054 Uiso 1 1 calc R . . C9 C 0.3720(4) 0.8630(2) 0.25711(18) 0.0377(5) Uani 1 1 d . . . H9A H 0.4611 0.9131 0.2259 0.045 Uiso 1 1 calc R . . C10 C -0.2082(4) 1.0572(2) 0.15481(18) 0.0369(5) Uani 1 1 d . . . H10A H -0.2305 1.0287 0.2294 0.044 Uiso 1 1 calc R . . C11 C -0.3867(4) 1.1582(2) 0.1121(2) 0.0507(7) Uani 1 1 d . . . H11A H -0.4206 1.1615 0.0375 0.061 Uiso 1 1 calc R . . H11B H -0.5150 1.1883 0.1590 0.061 Uiso 1 1 calc R . . C12 C -0.1703(4) 1.1759(2) 0.1369(2) 0.0433(6) Uani 1 1 d . . . C13 C -0.0778(5) 1.2547(3) 0.1949(3) 0.0626(8) Uani 1 1 d . . . H13A H 0.0266 1.2188 0.2504 0.075 Uiso 1 1 calc R . . H13B H -0.1740 1.3317 0.2087 0.075 Uiso 1 1 calc R . . C14 C -0.0031(5) 1.2332(2) 0.0825(2) 0.0552(7) Uani 1 1 d . . . H14A H -0.0538 1.2972 0.0278 0.066 Uiso 1 1 calc R . . H14B H 0.1468 1.1843 0.0695 0.066 Uiso 1 1 calc R . . O3 O 0.3859(3) 0.15136(19) 0.39831(16) 0.0601(5) Uani 1 1 d . . . O4 O 0.7071(3) 0.01719(15) 0.41823(14) 0.0518(5) Uani 1 1 d . . . N2 N 0.6883(3) 0.19456(17) 0.46530(14) 0.0353(4) Uani 1 1 d . . . C15 C 0.5745(4) 0.1258(2) 0.42595(18) 0.0421(6) Uani 1 1 d . . . C16 C 0.9258(5) 0.0149(2) 0.4502(2) 0.0522(7) Uani 1 1 d . . . H16A H 1.0320 0.0074 0.3895 0.063 Uiso 1 1 calc R . . H16B H 0.9760 -0.0518 0.5025 0.063 Uiso 1 1 calc R . . C17 C 0.9092(4) 0.1310(2) 0.49791(18) 0.0372(5) Uani 1 1 d . . . H17A H 1.0227 0.1709 0.4632 0.045 Uiso 1 1 calc R . . C18 C 0.9305(3) 0.12145(18) 0.61477(17) 0.0316(5) Uani 1 1 d . . . C19 C 0.7913(4) 0.0691(2) 0.68153(19) 0.0409(6) Uani 1 1 d . . . H19A H 0.6797 0.0399 0.6532 0.049 Uiso 1 1 calc R . . C20 C 0.8128(5) 0.0590(2) 0.7883(2) 0.0477(6) Uani 1 1 d . . . H20A H 0.7166 0.0231 0.8330 0.057 Uiso 1 1 calc R . . C21 C 0.9750(4) 0.1013(2) 0.8298(2) 0.0454(6) Uani 1 1 d . . . H21A H 0.9914 0.0939 0.9032 0.054 Uiso 1 1 calc R . . C22 C 1.1129(4) 0.1543(2) 0.7649(2) 0.0447(6) Uani 1 1 d . . . H22A H 1.2236 0.1839 0.7936 0.054 Uiso 1 1 calc R . . C23 C 1.0900(4) 0.1646(2) 0.65760(19) 0.0374(5) Uani 1 1 d . . . H23A H 1.1851 0.2016 0.6132 0.045 Uiso 1 1 calc R . . C24 C 0.5895(4) 0.3071(2) 0.5002(2) 0.0387(5) Uani 1 1 d . . . H24A H 0.5298 0.3079 0.5741 0.046 Uiso 1 1 calc R . . C25 C 0.4658(4) 0.4017(2) 0.4233(3) 0.0561(8) Uani 1 1 d . . . H25A H 0.4588 0.3823 0.3506 0.067 Uiso 1 1 calc R . . H25B H 0.3329 0.4568 0.4497 0.067 Uiso 1 1 calc R . . C26 C 0.6820(4) 0.4078(2) 0.4598(2) 0.0441(6) Uani 1 1 d . . . C27 C 0.7864(4) 0.4925(2) 0.5029(3) 0.0537(7) Uani 1 1 d . . . H27A H 0.8563 0.4699 0.5712 0.064 Uiso 1 1 calc R . . H27B H 0.7167 0.5766 0.4897 0.064 Uiso 1 1 calc R . . C28 C 0.8925(5) 0.4267(3) 0.4107(2) 0.0530(7) Uani 1 1 d . . . H28A H 0.8878 0.4706 0.3411 0.064 Uiso 1 1 calc R . . H28B H 1.0274 0.3639 0.4226 0.064 Uiso 1 1 calc R . . O5 O 0.0645(3) 0.48417(19) 0.72572(18) 0.0640(6) Uani 1 1 d . . . O6 O 0.3882(3) 0.36280(16) 0.76822(17) 0.0583(5) Uani 1 1 d . . . N3 N 0.3579(3) 0.55196(16) 0.77333(15) 0.0357(4) Uani 1 1 d . . . C29 C 0.2500(4) 0.4714(2) 0.7531(2) 0.0444(6) Uani 1 1 d . . . C30 C 0.6004(4) 0.3735(2) 0.7983(2) 0.0527(7) Uani 1 1 d . . . H30A H 0.7121 0.3555 0.7406 0.063 Uiso 1 1 calc R . . H30B H 0.6497 0.3193 0.8603 0.063 Uiso 1 1 calc R . . C31 C 0.5688(4) 0.5005(2) 0.8235(2) 0.0401(5) Uani 1 1 d . . . H31A H 0.6889 0.5348 0.7878 0.048 Uiso 1 1 calc R . . C32 C 0.5546(4) 0.5186(2) 0.9393(2) 0.0384(5) Uani 1 1 d . . . C33 C 0.3981(5) 0.4816(2) 1.0063(2) 0.0508(7) Uani 1 1 d . . . H33A H 0.2977 0.4430 0.9799 0.061 Uiso 1 1 calc R . . C34 C 0.3862(5) 0.5002(3) 1.1109(2) 0.0599(8) Uani 1 1 d . . . H34A H 0.2779 0.4743 1.1560 0.072 Uiso 1 1 calc R . . C35 C 0.5304(6) 0.5560(3) 1.1502(2) 0.0620(8) Uani 1 1 d . . . H35A H 0.5221 0.5689 1.2222 0.074 Uiso 1 1 calc R . . C36 C 0.6864(5) 0.5928(3) 1.0843(3) 0.0612(8) Uani 1 1 d . . . H36A H 0.7869 0.6310 1.1110 0.073 Uiso 1 1 calc R . . C37 C 0.6988(4) 0.5749(2) 0.9793(2) 0.0482(6) Uani 1 1 d . . . H37A H 0.8069 0.6013 0.9344 0.058 Uiso 1 1 calc R . . C38 C 0.2528(3) 0.67258(19) 0.78120(18) 0.0340(5) Uani 1 1 d . . . H38A H 0.1906 0.6942 0.8519 0.041 Uiso 1 1 calc R . . C39 C 0.1319(4) 0.7433(2) 0.6892(2) 0.0486(6) Uani 1 1 d . . . H39A H 0.1275 0.7031 0.6255 0.058 Uiso 1 1 calc R . . H39B H -0.0018 0.8047 0.7040 0.058 Uiso 1 1 calc R . . C40 C 0.3475(4) 0.7612(2) 0.7172(2) 0.0411(6) Uani 1 1 d . . . C41 C 0.4491(5) 0.8572(2) 0.7367(3) 0.0560(7) Uani 1 1 d . . . H41A H 0.5152 0.8543 0.8052 0.067 Uiso 1 1 calc R . . H41B H 0.3806 0.9367 0.7060 0.067 Uiso 1 1 calc R . . C42 C 0.5604(4) 0.7664(3) 0.6625(2) 0.0510(6) Uani 1 1 d . . . H42A H 0.5594 0.7904 0.5867 0.061 Uiso 1 1 calc R . . H42B H 0.6940 0.7080 0.6859 0.061 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 0.0325(9) 0.0714(12) 0.0407(9) -0.0091(8) -0.0007(7) -0.0179(8) O2 0.0405(9) 0.0482(10) 0.0383(9) -0.0135(7) 0.0024(7) -0.0125(8) N1 0.0247(9) 0.0369(10) 0.0321(10) -0.0049(8) -0.0015(7) -0.0031(8) C1 0.0348(13) 0.0442(13) 0.0261(11) -0.0007(9) 0.0017(9) -0.0128(10) C2 0.0345(12) 0.0457(14) 0.0334(12) -0.0084(10) -0.0026(9) -0.0024(10) C3 0.0242(10) 0.0359(12) 0.0318(11) -0.0027(9) 0.0004(8) -0.0042(9) C4 0.0280(11) 0.0303(11) 0.0310(11) -0.0073(9) 0.0011(9) -0.0033(9) C5 0.0393(13) 0.0381(13) 0.0403(13) -0.0037(10) -0.0054(10) -0.0114(10) C6 0.0484(15) 0.0384(13) 0.0452(14) -0.0003(11) 0.0031(11) -0.0137(11) C7 0.0470(15) 0.0427(14) 0.0344(12) 0.0008(10) -0.0015(10) -0.0003(11) C8 0.0353(13) 0.0593(16) 0.0382(13) -0.0067(12) -0.0081(10) -0.0054(12) C9 0.0323(12) 0.0470(14) 0.0348(12) -0.0036(10) 0.0011(9) -0.0114(10) C10 0.0291(11) 0.0449(13) 0.0334(12) -0.0081(10) 0.0029(9) -0.0012(10) C11 0.0306(13) 0.0520(16) 0.0639(17) -0.0137(13) -0.0050(12) 0.0057(11) C12 0.0349(13) 0.0402(14) 0.0510(15) -0.0105(11) -0.0059(11) 0.0026(11) C13 0.0639(19) 0.0453(16) 0.078(2) -0.0235(15) -0.0172(15) 0.0002(14) C14 0.0540(16) 0.0461(16) 0.0678(19) 0.0021(13) -0.0176(14) -0.0153(13) O3 0.0356(10) 0.0839(14) 0.0694(13) -0.0295(11) 0.0032(9) -0.0234(10) O4 0.0546(11) 0.0513(11) 0.0540(11) -0.0229(9) 0.0139(9) -0.0180(9) N2 0.0296(10) 0.0389(11) 0.0378(11) -0.0027(8) -0.0047(8) -0.0079(8) C15 0.0428(15) 0.0543(15) 0.0335(13) -0.0113(11) 0.0114(10) -0.0200(12) C16 0.0596(17) 0.0494(16) 0.0421(14) -0.0125(12) -0.0037(12) 0.0022(13) C17 0.0323(12) 0.0417(13) 0.0350(12) -0.0018(10) -0.0005(9) -0.0042(10) C18 0.0305(11) 0.0249(10) 0.0367(12) -0.0013(9) 0.0001(9) -0.0019(9) C19 0.0437(14) 0.0427(14) 0.0396(14) 0.0030(11) -0.0039(11) -0.0187(11) C20 0.0597(17) 0.0449(15) 0.0396(14) 0.0063(11) 0.0021(12) -0.0193(13) C21 0.0613(17) 0.0365(13) 0.0354(13) -0.0016(10) -0.0096(12) -0.0042(12) C22 0.0478(14) 0.0378(13) 0.0504(15) -0.0050(11) -0.0117(12) -0.0106(11) C23 0.0316(11) 0.0331(12) 0.0466(14) 0.0006(10) -0.0016(10) -0.0073(9) C24 0.0302(11) 0.0382(13) 0.0468(14) -0.0035(10) -0.0025(10) -0.0059(10) C25 0.0388(14) 0.0440(15) 0.086(2) 0.0092(14) -0.0237(14) -0.0110(12) C26 0.0351(13) 0.0401(14) 0.0576(16) 0.0016(12) -0.0128(11) -0.0093(11) C27 0.0442(15) 0.0438(14) 0.0755(19) -0.0087(13) -0.0094(13) -0.0117(12) C28 0.0527(16) 0.0547(17) 0.0582(17) -0.0008(13) -0.0075(13) -0.0260(13) O5 0.0400(11) 0.0699(13) 0.0925(16) -0.0353(12) -0.0040(10) -0.0220(10) O6 0.0489(11) 0.0389(10) 0.0911(15) -0.0263(10) 0.0071(10) -0.0127(9) N3 0.0278(10) 0.0354(11) 0.0457(12) -0.0125(9) -0.0022(8) -0.0070(8) C29 0.0390(14) 0.0434(14) 0.0546(16) -0.0220(12) 0.0079(11) -0.0127(11) C30 0.0453(15) 0.0423(15) 0.0673(18) -0.0165(13) -0.0001(13) 0.0003(12) C31 0.0291(12) 0.0394(13) 0.0511(14) -0.0076(11) 0.0001(10) -0.0055(10) C32 0.0336(12) 0.0300(11) 0.0483(14) -0.0040(10) -0.0066(10) 0.0008(9) C33 0.0491(16) 0.0519(16) 0.0525(17) -0.0020(12) -0.0054(12) -0.0138(13) C34 0.0624(19) 0.0580(18) 0.0520(17) 0.0040(14) -0.0001(14) -0.0028(15) C35 0.079(2) 0.0473(17) 0.0499(17) -0.0041(13) -0.0178(16) 0.0085(16) C36 0.070(2) 0.0437(15) 0.071(2) -0.0116(14) -0.0301(17) -0.0055(14) C37 0.0440(14) 0.0431(14) 0.0583(17) -0.0044(12) -0.0136(12) -0.0086(11) C38 0.0284(11) 0.0357(12) 0.0387(12) -0.0085(10) 0.0012(9) -0.0074(9) C39 0.0344(13) 0.0525(15) 0.0560(16) 0.0073(12) -0.0058(11) -0.0076(12) C40 0.0329(12) 0.0395(13) 0.0505(14) -0.0024(11) -0.0007(10) -0.0080(10) C41 0.0525(16) 0.0414(15) 0.076(2) -0.0080(13) 0.0115(14) -0.0163(13) C42 0.0439(14) 0.0583(17) 0.0549(16) -0.0064(13) 0.0067(12) -0.0215(13) _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 C1 1.208(3) . ? O2 C1 1.360(3) . ? O2 C2 1.450(3) . ? N1 C1 1.353(3) . ? N1 C10 1.439(3) . ? N1 C3 1.461(3) . ? C2 C3 1.538(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.515(3) . ? C3 H3A 1.0000 . ? C4 C9 1.382(3) . ? C4 C5 1.389(3) . ? C5 C6 1.381(3) . ? C5 H5A 0.9500 . ? C6 C7 1.375(3) . ? C6 H6A 0.9500 . ? C7 C8 1.376(4) . ? C7 H7A 0.9500 . ? C8 C9 1.387(3) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C12 1.471(4) . ? C10 C11 1.513(3) . ? C10 H10A 1.0000 . ? C11 C12 1.470(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.479(4) . ? C12 C13 1.481(4) . ? C13 C14 1.520(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? O3 C15 1.209(3) . ? O4 C15 1.362(3) . ? O4 C16 1.440(3) . ? N2 C15 1.346(3) . ? N2 C24 1.430(3) . ? N2 C17 1.469(3) . ? C16 C17 1.535(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.509(3) . ? C17 H17A 1.0000 . ? C18 C23 1.381(3) . ? C18 C19 1.391(3) . ? C19 C20 1.380(3) . ? C19 H19A 0.9500 . ? C20 C21 1.382(4) . ? C20 H20A 0.9500 . ? C21 C22 1.377(4) . ? C21 H21A 0.9500 . ? C22 C23 1.388(4) . ? C22 H22A 0.9500 . ? C23 H23A 0.9500 . ? C24 C26 1.480(3) . ? C24 C25 1.517(4) . ? C24 H24A 1.0000 . ? C25 C26 1.472(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C28 1.477(4) . ? C26 C27 1.479(4) . ? C27 C28 1.514(4) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? O5 C29 1.200(3) . ? O6 C29 1.371(3) . ? O6 C30 1.436(3) . ? N3 C29 1.339(3) . ? N3 C38 1.432(3) . ? N3 C31 1.471(3) . ? C30 C31 1.531(3) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.521(4) . ? C31 H31A 1.0000 . ? C32 C37 1.383(3) . ? C32 C33 1.383(4) . ? C33 C34 1.381(4) . ? C33 H33A 0.9500 . ? C34 C35 1.376(4) . ? C34 H34A 0.9500 . ? C35 C36 1.373(5) . ? C35 H35A 0.9500 . ? C36 C37 1.382(4) . ? C36 H36A 0.9500 . ? C37 H37A 0.9500 . ? C38 C40 1.480(3) . ? C38 C39 1.514(3) . ? C38 H38A 1.0000 . ? C39 C40 1.478(3) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.470(4) . ? C40 C42 1.475(3) . ? C41 C42 1.520(4) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? 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 C1 O2 C2 109.09(17) . . ? C1 N1 C10 124.88(18) . . ? C1 N1 C3 112.27(18) . . ? C10 N1 C3 120.06(17) . . ? O1 C1 N1 128.8(2) . . ? O1 C1 O2 121.8(2) . . ? N1 C1 O2 109.34(18) . . ? O2 C2 C3 104.95(17) . . ? O2 C2 H2A 110.8 . . ? C3 C2 H2A 110.8 . . ? O2 C2 H2B 110.8 . . ? C3 C2 H2B 110.8 . . ? H2A C2 H2B 108.8 . . ? N1 C3 C4 113.62(17) . . ? N1 C3 C2 99.39(17) . . ? C4 C3 C2 114.18(19) . . ? N1 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? C9 C4 C5 118.6(2) . . ? C9 C4 C3 119.54(19) . . ? C5 C4 C3 121.83(19) . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C7 C6 C5 120.4(2) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C6 C7 C8 119.7(2) . . ? C6 C7 H7A 120.1 . . ? C8 C7 H7A 120.1 . . ? C7 C8 C9 120.0(2) . . ? C7 C8 H8A 120.0 . . ? C9 C8 H8A 120.0 . . ? C4 C9 C8 120.7(2) . . ? C4 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? N1 C10 C12 118.8(2) . . ? N1 C10 C11 119.6(2) . . ? C12 C10 C11 59.01(16) . . ? N1 C10 H10A 115.8 . . ? C12 C10 H10A 115.8 . . ? C11 C10 H10A 115.8 . . ? C12 C11 C10 59.10(16) . . ? C12 C11 H11A 117.9 . . ? C10 C11 H11A 117.9 . . ? C12 C11 H11B 117.9 . . ? C10 C11 H11B 117.9 . . ? H11A C11 H11B 115.0 . . ? C11 C12 C10 61.89(17) . . ? C11 C12 C14 135.8(2) . . ? C10 C12 C14 137.5(2) . . ? C11 C12 C13 139.2(2) . . ? C10 C12 C13 137.0(2) . . ? C14 C12 C13 61.8(2) . . ? C12 C13 C14 59.04(18) . . ? C12 C13 H13A 117.9 . . ? C14 C13 H13A 117.9 . . ? C12 C13 H13B 117.9 . . ? C14 C13 H13B 117.9 . . ? H13A C13 H13B 115.0 . . ? C12 C14 C13 59.15(19) . . ? C12 C14 H14A 117.9 . . ? C13 C14 H14A 117.9 . . ? C12 C14 H14B 117.9 . . ? C13 C14 H14B 117.9 . . ? H14A C14 H14B 115.0 . . ? C15 O4 C16 109.83(18) . . ? C15 N2 C24 124.0(2) . . ? C15 N2 C17 113.0(2) . . ? C24 N2 C17 120.79(18) . . ? O3 C15 N2 128.1(2) . . ? O3 C15 O4 122.3(2) . . ? N2 C15 O4 109.5(2) . . ? O4 C16 C17 106.1(2) . . ? O4 C16 H16A 110.5 . . ? C17 C16 H16A 110.5 . . ? O4 C16 H16B 110.5 . . ? C17 C16 H16B 110.5 . . ? H16A C16 H16B 108.7 . . ? N2 C17 C18 112.66(18) . . ? N2 C17 C16 100.06(19) . . ? C18 C17 C16 115.1(2) . . ? N2 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? C23 C18 C19 118.6(2) . . ? C23 C18 C17 120.3(2) . . ? C19 C18 C17 121.1(2) . . ? C20 C19 C18 121.0(2) . . ? C20 C19 H19A 119.5 . . ? C18 C19 H19A 119.5 . . ? C19 C20 C21 119.7(2) . . ? C19 C20 H20A 120.2 . . ? C21 C20 H20A 120.2 . . ? C22 C21 C20 120.1(2) . . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C21 C22 C23 120.0(2) . . ? C21 C22 H22A 120.0 . . ? C23 C22 H22A 120.0 . . ? C18 C23 C22 120.7(2) . . ? C18 C23 H23A 119.7 . . ? C22 C23 H23A 119.7 . . ? N2 C24 C26 118.9(2) . . ? N2 C24 C25 119.0(2) . . ? C26 C24 C25 58.84(16) . . ? N2 C24 H24A 116.0 . . ? C26 C24 H24A 116.0 . . ? C25 C24 H24A 116.0 . . ? C26 C25 C24 59.31(16) . . ? C26 C25 H25A 117.8 . . ? C24 C25 H25A 117.8 . . ? C26 C25 H25B 117.8 . . ? C24 C25 H25B 117.8 . . ? H25A C25 H25B 115.0 . . ? C25 C26 C28 136.2(3) . . ? C25 C26 C27 139.2(2) . . ? C28 C26 C27 61.62(18) . . ? C25 C26 C24 61.85(17) . . ? C28 C26 C24 137.2(2) . . ? C27 C26 C24 137.2(3) . . ? C26 C27 C28 59.13(18) . . ? C26 C27 H27A 117.9 . . ? C28 C27 H27A 117.9 . . ? C26 C27 H27B 117.9 . . ? C28 C27 H27B 117.9 . . ? H27A C27 H27B 115.0 . . ? C26 C28 C27 59.25(18) . . ? C26 C28 H28A 117.8 . . ? C27 C28 H28A 117.8 . . ? C26 C28 H28B 117.8 . . ? C27 C28 H28B 117.8 . . ? H28A C28 H28B 115.0 . . ? C29 O6 C30 109.85(19) . . ? C29 N3 C38 123.52(19) . . ? C29 N3 C31 112.7(2) . . ? C38 N3 C31 120.30(18) . . ? O5 C29 N3 129.4(3) . . ? O5 C29 O6 121.6(2) . . ? N3 C29 O6 108.9(2) . . ? O6 C30 C31 105.7(2) . . ? O6 C30 H30A 110.6 . . ? C31 C30 H30A 110.6 . . ? O6 C30 H30B 110.6 . . ? C31 C30 H30B 110.6 . . ? H30A C30 H30B 108.7 . . ? N3 C31 C32 111.96(19) . . ? N3 C31 C30 99.66(19) . . ? C32 C31 C30 114.9(2) . . ? N3 C31 H31A 110.0 . . ? C32 C31 H31A 110.0 . . ? C30 C31 H31A 110.0 . . ? C37 C32 C33 118.7(2) . . ? C37 C32 C31 119.7(2) . . ? C33 C32 C31 121.6(2) . . ? C34 C33 C32 120.7(3) . . ? C34 C33 H33A 119.7 . . ? C32 C33 H33A 119.7 . . ? C35 C34 C33 120.3(3) . . ? C35 C34 H34A 119.8 . . ? C33 C34 H34A 119.8 . . ? C36 C35 C34 119.3(3) . . ? C36 C35 H35A 120.4 . . ? C34 C35 H35A 120.4 . . ? C35 C36 C37 120.7(3) . . ? C35 C36 H36A 119.7 . . ? C37 C36 H36A 119.7 . . ? C36 C37 C32 120.3(3) . . ? C36 C37 H37A 119.8 . . ? C32 C37 H37A 119.8 . . ? N3 C38 C40 117.95(19) . . ? N3 C38 C39 119.7(2) . . ? C40 C38 C39 59.13(16) . . ? N3 C38 H38A 116.0 . . ? C40 C38 H38A 116.0 . . ? C39 C38 H38A 116.0 . . ? C40 C39 C38 59.30(16) . . ? C40 C39 H39A 117.8 . . ? C38 C39 H39A 117.8 . . ? C40 C39 H39B 117.8 . . ? C38 C39 H39B 117.8 . . ? H39A C39 H39B 115.0 . . ? C41 C40 C42 62.13(18) . . ? C41 C40 C39 139.3(2) . . ? C42 C40 C39 136.6(2) . . ? C41 C40 C38 136.6(2) . . ? C42 C40 C38 136.9(2) . . ? C39 C40 C38 61.57(16) . . ? C40 C41 C42 59.11(17) . . ? C40 C41 H41A 117.9 . . ? C42 C41 H41A 117.9 . . ? C40 C41 H41B 117.9 . . ? C42 C41 H41B 117.9 . . ? H41A C41 H41B 115.0 . . ? C40 C42 C41 58.76(17) . . ? C40 C42 H42A 117.9 . . ? C41 C42 H42A 117.9 . . ? C40 C42 H42B 117.9 . . ? C41 C42 H42B 117.9 . . ? H42A C42 H42B 115.0 . . ? 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 C10 N1 C1 O1 10.4(4) . . . . ? C3 N1 C1 O1 171.4(2) . . . . ? C10 N1 C1 O2 -171.0(2) . . . . ? C3 N1 C1 O2 -10.1(2) . . . . ? C2 O2 C1 O1 173.2(2) . . . . ? C2 O2 C1 N1 -5.4(2) . . . . ? C1 O2 C2 C3 17.5(2) . . . . ? C1 N1 C3 C4 -102.1(2) . . . . ? C10 N1 C3 C4 59.9(3) . . . . ? C1 N1 C3 C2 19.6(2) . . . . ? C10 N1 C3 C2 -178.4(2) . . . . ? O2 C2 C3 N1 -21.3(2) . . . . ? O2 C2 C3 C4 100.0(2) . . . . ? N1 C3 C4 C9 -137.6(2) . . . . ? C2 C3 C4 C9 109.3(2) . . . . ? N1 C3 C4 C5 43.9(3) . . . . ? C2 C3 C4 C5 -69.1(3) . . . . ? C9 C4 C5 C6 -1.4(3) . . . . ? C3 C4 C5 C6 177.1(2) . . . . ? C4 C5 C6 C7 0.2(4) . . . . ? C5 C6 C7 C8 1.1(4) . . . . ? C6 C7 C8 C9 -1.2(4) . . . . ? C5 C4 C9 C8 1.2(3) . . . . ? C3 C4 C9 C8 -177.3(2) . . . . ? C7 C8 C9 C4 0.1(4) . . . . ? C1 N1 C10 C12 -124.2(2) . . . . ? C3 N1 C10 C12 76.2(3) . . . . ? C1 N1 C10 C11 -55.5(3) . . . . ? C3 N1 C10 C11 144.9(2) . . . . ? N1 C10 C11 C12 -107.7(2) . . . . ? C10 C11 C12 C14 130.6(3) . . . . ? C10 C11 C12 C13 -130.5(4) . . . . ? N1 C10 C12 C11 109.2(2) . . . . ? N1 C10 C12 C14 -19.2(4) . . . . ? C11 C10 C12 C14 -128.3(4) . . . . ? N1 C10 C12 C13 -117.5(3) . . . . ? C11 C10 C12 C13 133.3(4) . . . . ? C11 C12 C13 C14 -128.6(4) . . . . ? C10 C12 C13 C14 130.7(3) . . . . ? C11 C12 C14 C13 133.0(3) . . . . ? C10 C12 C14 C13 -130.0(4) . . . . ? C24 N2 C15 O3 12.6(4) . . . . ? C17 N2 C15 O3 175.5(2) . . . . ? C24 N2 C15 O4 -168.8(2) . . . . ? C17 N2 C15 O4 -5.9(3) . . . . ? C16 O4 C15 O3 176.1(2) . . . . ? C16 O4 C15 N2 -2.6(3) . . . . ? C15 O4 C16 C17 9.4(3) . . . . ? C15 N2 C17 C18 -111.9(2) . . . . ? C24 N2 C17 C18 51.7(3) . . . . ? C15 N2 C17 C16 10.9(2) . . . . ? C24 N2 C17 C16 174.5(2) . . . . ? O4 C16 C17 N2 -11.7(2) . . . . ? O4 C16 C17 C18 109.4(2) . . . . ? N2 C17 C18 C23 -122.3(2) . . . . ? C16 C17 C18 C23 123.8(2) . . . . ? N2 C17 C18 C19 57.9(3) . . . . ? C16 C17 C18 C19 -56.0(3) . . . . ? C23 C18 C19 C20 -0.7(3) . . . . ? C17 C18 C19 C20 179.1(2) . . . . ? C18 C19 C20 C21 0.0(4) . . . . ? C19 C20 C21 C22 0.6(4) . . . . ? C20 C21 C22 C23 -0.5(4) . . . . ? C19 C18 C23 C22 0.9(3) . . . . ? C17 C18 C23 C22 -179.0(2) . . . . ? C21 C22 C23 C18 -0.3(4) . . . . ? C15 N2 C24 C26 -128.3(2) . . . . ? C17 N2 C24 C26 70.0(3) . . . . ? C15 N2 C24 C25 -60.0(3) . . . . ? C17 N2 C24 C25 138.3(2) . . . . ? N2 C24 C25 C26 -108.0(2) . . . . ? C24 C25 C26 C28 130.1(4) . . . . ? C24 C25 C26 C27 -130.9(4) . . . . ? N2 C24 C26 C25 108.3(3) . . . . ? N2 C24 C26 C28 -20.6(4) . . . . ? C25 C24 C26 C28 -128.9(4) . . . . ? N2 C24 C26 C27 -118.5(3) . . . . ? C25 C24 C26 C27 133.3(4) . . . . ? C25 C26 C27 C28 -129.0(4) . . . . ? C24 C26 C27 C28 130.1(4) . . . . ? C25 C26 C28 C27 132.8(4) . . . . ? C24 C26 C28 C27 -130.1(4) . . . . ? C38 N3 C29 O5 10.4(4) . . . . ? C31 N3 C29 O5 169.3(3) . . . . ? C38 N3 C29 O6 -169.9(2) . . . . ? C31 N3 C29 O6 -10.9(3) . . . . ? C30 O6 C29 O5 178.7(3) . . . . ? C30 O6 C29 N3 -1.1(3) . . . . ? C29 O6 C30 C31 11.8(3) . . . . ? C29 N3 C31 C32 -105.0(2) . . . . ? C38 N3 C31 C32 54.7(3) . . . . ? C29 N3 C31 C30 17.0(3) . . . . ? C38 N3 C31 C30 176.7(2) . . . . ? O6 C30 C31 N3 -16.4(3) . . . . ? O6 C30 C31 C32 103.4(2) . . . . ? N3 C31 C32 C37 -123.1(2) . . . . ? C30 C31 C32 C37 124.2(2) . . . . ? N3 C31 C32 C33 56.0(3) . . . . ? C30 C31 C32 C33 -56.8(3) . . . . ? C37 C32 C33 C34 -0.1(4) . . . . ? C31 C32 C33 C34 -179.2(2) . . . . ? C32 C33 C34 C35 0.0(4) . . . . ? C33 C34 C35 C36 -0.1(4) . . . . ? C34 C35 C36 C37 0.3(4) . . . . ? C35 C36 C37 C32 -0.4(4) . . . . ? C33 C32 C37 C36 0.3(4) . . . . ? C31 C32 C37 C36 179.4(2) . . . . ? C29 N3 C38 C40 -127.6(2) . . . . ? C31 N3 C38 C40 75.0(3) . . . . ? C29 N3 C38 C39 -59.1(3) . . . . ? C31 N3 C38 C39 143.5(2) . . . . ? N3 C38 C39 C40 -106.7(2) . . . . ? C38 C39 C40 C41 -129.7(4) . . . . ? C38 C39 C40 C42 129.5(3) . . . . ? N3 C38 C40 C41 -117.3(3) . . . . ? C39 C38 C40 C41 133.1(4) . . . . ? N3 C38 C40 C42 -19.5(4) . . . . ? C39 C38 C40 C42 -129.1(4) . . . . ? N3 C38 C40 C39 109.6(2) . . . . ? C39 C40 C41 C42 -130.2(4) . . . . ? C38 C40 C41 C42 130.1(3) . . . . ? C39 C40 C42 C41 133.6(4) . . . . ? C38 C40 C42 C41 -129.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.160 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.027 # Attachment 'amino-spiro[2.2]pentanes_08086t.cif' data_08086t _database_code_depnum_ccdc_archive 'CCDC 729829' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 08086t _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 N O2' _chemical_formula_sum 'C14 H15 N O2' _chemical_formula_weight 229.27 _chemical_absolute_configuration rm 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.4331(18) _cell_length_b 11.657(3) _cell_length_c 15.860(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1189.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3152 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 24.74 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9584 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details 'TWINABS, G. Sheldrick, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1265 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1265 _reflns_number_gt 1114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _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. The sample was cracked, thus a twin model was used to correct the data. A preliminary set of cell constants was calculated from reflections harvested from one set of 100 frames using CellNow. Of the 273 reflections used, 77 indexed exclusively to component 1, 44 indexed exclusively to component 2, and 145 were common to both. The remaining 7 reflections were not indexed to either component and were discarded. There is a 1.9 degree rotation between the two components. The rotation matrix is [-1 0 0.013 0 1 0 -0.08 -0.011 1]. The BASF value refined to 0.38 (a 62:38 'twin'). The statistics before the 'twin' model were: R1 = 0.0520, WR2 = 0.1427, largest difference peak = 0.30 electrons, and C-C(esd) = 0.0053 angstroms. The statistics after the "twin" model are: R1 = 0.0329, WR2 = 0.0815, largest difference peak = 0.13 electrons, and C-C(esd) = 0.0035 angstroms. ; _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^)+(0.0359P)^2^+0.2543P] 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), 862 Friedel Pairs, Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 5(2) _refine_ls_number_reflns 1265 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0815 _refine_ls_wR_factor_gt 0.0756 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.6240(3) 0.42953(14) 0.29333(12) 0.0416(5) Uani 1 1 d . . . O2 O 0.3211(3) 0.49125(13) 0.34760(11) 0.0397(5) Uani 1 1 d . . . N1 N 0.3119(3) 0.34046(15) 0.26306(12) 0.0283(5) Uani 1 1 d . . . C1 C 0.4371(4) 0.41854(18) 0.29989(14) 0.0308(6) Uani 1 1 d . . . C2 C 0.1050(4) 0.4587(2) 0.34287(18) 0.0399(7) Uani 1 1 d . . . H2A H 0.0244 0.5167 0.3111 0.048 Uiso 1 1 calc R . . H2B H 0.0449 0.4514 0.4001 0.048 Uiso 1 1 calc R . . C3 C 0.1006(4) 0.34219(18) 0.29686(15) 0.0304(6) Uani 1 1 d . . . H3A H -0.0016 0.3454 0.2494 0.036 Uiso 1 1 calc R . . C4 C 0.0529(3) 0.24001(18) 0.35251(14) 0.0281(5) Uani 1 1 d . . . C5 C 0.1745(5) 0.2141(2) 0.42230(16) 0.0392(6) Uani 1 1 d . . . H5A H 0.2909 0.2609 0.4355 0.047 Uiso 1 1 calc R . . C6 C 0.1283(5) 0.1211(2) 0.47272(17) 0.0457(7) Uani 1 1 d . . . H6A H 0.2118 0.1051 0.5207 0.055 Uiso 1 1 calc R . . C7 C -0.0376(5) 0.0517(2) 0.45395(18) 0.0493(8) Uani 1 1 d . . . H7A H -0.0681 -0.0129 0.4883 0.059 Uiso 1 1 calc R . . C8 C -0.1590(5) 0.0762(2) 0.38520(18) 0.0529(8) Uani 1 1 d . . . H8A H -0.2740 0.0283 0.3719 0.063 Uiso 1 1 calc R . . C9 C -0.1146(4) 0.1706(2) 0.33479(17) 0.0415(6) Uani 1 1 d . . . H9A H -0.2006 0.1874 0.2877 0.050 Uiso 1 1 calc R . . C10 C 0.3900(4) 0.24610(17) 0.21415(14) 0.0278(5) Uani 1 1 d . . . H10A H 0.4424 0.1783 0.2464 0.033 Uiso 1 1 calc R . . C11 C 0.2820(4) 0.2209(2) 0.13074(15) 0.0373(6) Uani 1 1 d . . . H11A H 0.2672 0.1396 0.1136 0.045 Uiso 1 1 calc R . . H11B H 0.1659 0.2715 0.1136 0.045 Uiso 1 1 calc R . . C12 C 0.4931(4) 0.27024(19) 0.13280(14) 0.0298(6) Uani 1 1 d . . . C13 C 0.6031(4) 0.3680(2) 0.09379(16) 0.0385(6) Uani 1 1 d . . . H13A H 0.6638 0.4267 0.1316 0.046 Uiso 1 1 calc R . . H13B H 0.5496 0.3977 0.0395 0.046 Uiso 1 1 calc R . . C14 C 0.6981(4) 0.2488(2) 0.09466(16) 0.0366(6) Uani 1 1 d . . . H14A H 0.7027 0.2058 0.0408 0.044 Uiso 1 1 calc R . . H14B H 0.8169 0.2347 0.1330 0.044 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 0.0288(11) 0.0431(9) 0.0528(11) -0.0085(9) -0.0009(9) -0.0066(8) O2 0.0392(11) 0.0322(8) 0.0478(11) -0.0101(8) 0.0065(9) -0.0018(8) N1 0.0239(11) 0.0270(9) 0.0340(11) -0.0036(8) 0.0048(9) -0.0013(9) C1 0.0339(16) 0.0264(11) 0.0321(12) -0.0002(11) 0.0023(11) -0.0006(11) C2 0.0372(15) 0.0300(11) 0.0526(16) -0.0027(12) 0.0124(14) 0.0019(11) C3 0.0254(13) 0.0311(10) 0.0347(12) 0.0010(11) 0.0053(11) 0.0011(11) C4 0.0246(12) 0.0287(10) 0.0309(12) -0.0049(10) 0.0058(10) 0.0014(10) C5 0.0349(15) 0.0394(13) 0.0433(14) -0.0006(12) -0.0012(13) -0.0032(13) C6 0.0518(19) 0.0447(14) 0.0405(14) 0.0057(12) 0.0017(14) 0.0100(14) C7 0.071(2) 0.0327(12) 0.0445(16) 0.0013(12) 0.0214(16) -0.0005(15) C8 0.060(2) 0.0459(14) 0.0528(17) -0.0058(14) 0.0117(16) -0.0258(16) C9 0.0374(15) 0.0485(14) 0.0385(13) -0.0022(12) 0.0015(12) -0.0106(13) C10 0.0255(12) 0.0256(10) 0.0322(12) -0.0003(10) 0.0032(10) -0.0002(10) C11 0.0287(14) 0.0476(14) 0.0356(13) -0.0064(12) 0.0025(11) -0.0073(12) C12 0.0288(13) 0.0314(11) 0.0293(12) -0.0017(10) 0.0020(10) -0.0020(11) C13 0.0414(16) 0.0356(12) 0.0384(13) 0.0058(11) 0.0105(13) -0.0027(13) C14 0.0314(14) 0.0404(13) 0.0379(14) -0.0010(12) 0.0085(12) 0.0011(13) _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 C1 1.214(3) . ? O2 C1 1.359(3) . ? O2 C2 1.443(3) . ? N1 C1 1.349(3) . ? N1 C10 1.437(3) . ? N1 C3 1.461(3) . ? C2 C3 1.542(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.514(3) . ? C3 H3A 1.0000 . ? C4 C9 1.376(3) . ? C4 C5 1.389(4) . ? C5 C6 1.379(4) . ? C5 H5A 0.9500 . ? C6 C7 1.372(4) . ? C6 H6A 0.9500 . ? C7 C8 1.371(4) . ? C7 H7A 0.9500 . ? C8 C9 1.390(4) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C12 1.478(3) . ? C10 C11 1.523(3) . ? C10 H10A 1.0000 . ? C11 C12 1.476(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.472(3) . ? C12 C13 1.477(3) . ? C13 C14 1.519(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 C1 O2 C2 109.62(18) . . ? C1 N1 C10 122.8(2) . . ? C1 N1 C3 112.79(18) . . ? C10 N1 C3 122.27(18) . . ? O1 C1 N1 128.8(2) . . ? O1 C1 O2 121.7(2) . . ? N1 C1 O2 109.5(2) . . ? O2 C2 C3 105.91(19) . . ? O2 C2 H2A 110.6 . . ? C3 C2 H2A 110.6 . . ? O2 C2 H2B 110.6 . . ? C3 C2 H2B 110.6 . . ? H2A C2 H2B 108.7 . . ? N1 C3 C4 113.05(19) . . ? N1 C3 C2 99.72(18) . . ? C4 C3 C2 114.88(19) . . ? N1 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? C9 C4 C5 118.4(2) . . ? C9 C4 C3 120.1(2) . . ? C5 C4 C3 121.4(2) . . ? C6 C5 C4 120.8(3) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C7 C6 C5 120.4(3) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C8 C7 C6 119.5(2) . . ? C8 C7 H7A 120.2 . . ? C6 C7 H7A 120.2 . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8A 119.8 . . ? C9 C8 H8A 119.8 . . ? C4 C9 C8 120.6(3) . . ? C4 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? N1 C10 C12 118.86(18) . . ? N1 C10 C11 117.2(2) . . ? C12 C10 C11 58.89(16) . . ? N1 C10 H10A 116.5 . . ? C12 C10 H10A 116.5 . . ? C11 C10 H10A 116.5 . . ? C12 C11 C10 59.03(16) . . ? C12 C11 H11A 117.9 . . ? C10 C11 H11A 117.9 . . ? C12 C11 H11B 117.9 . . ? C10 C11 H11B 117.9 . . ? H11A C11 H11B 115.0 . . ? C14 C12 C11 138.5(2) . . ? C14 C12 C13 61.99(17) . . ? C11 C12 C13 137.1(2) . . ? C14 C12 C10 136.8(2) . . ? C11 C12 C10 62.08(16) . . ? C13 C12 C10 136.7(2) . . ? C12 C13 C14 58.84(16) . . ? C12 C13 H13A 117.9 . . ? C14 C13 H13A 117.9 . . ? C12 C13 H13B 117.9 . . ? C14 C13 H13B 117.9 . . ? H13A C13 H13B 115.0 . . ? C12 C14 C13 59.18(16) . . ? C12 C14 H14A 117.9 . . ? C13 C14 H14A 117.9 . . ? C12 C14 H14B 117.9 . . ? C13 C14 H14B 117.9 . . ? H14A C14 H14B 115.0 . . ? 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 C10 N1 C1 O1 6.8(4) . . . . ? C3 N1 C1 O1 170.5(2) . . . . ? C10 N1 C1 O2 -174.76(19) . . . . ? C3 N1 C1 O2 -11.1(3) . . . . ? C2 O2 C1 O1 179.3(2) . . . . ? C2 O2 C1 N1 0.6(3) . . . . ? C1 O2 C2 C3 9.0(3) . . . . ? C1 N1 C3 C4 -107.0(2) . . . . ? C10 N1 C3 C4 56.8(3) . . . . ? C1 N1 C3 C2 15.5(2) . . . . ? C10 N1 C3 C2 179.3(2) . . . . ? O2 C2 C3 N1 -14.0(2) . . . . ? O2 C2 C3 C4 107.1(2) . . . . ? N1 C3 C4 C9 -124.3(2) . . . . ? C2 C3 C4 C9 122.1(2) . . . . ? N1 C3 C4 C5 56.0(3) . . . . ? C2 C3 C4 C5 -57.5(3) . . . . ? C9 C4 C5 C6 -0.1(4) . . . . ? C3 C4 C5 C6 179.6(2) . . . . ? C4 C5 C6 C7 0.9(4) . . . . ? C5 C6 C7 C8 -0.8(4) . . . . ? C6 C7 C8 C9 0.0(4) . . . . ? C5 C4 C9 C8 -0.7(4) . . . . ? C3 C4 C9 C8 179.6(2) . . . . ? C7 C8 C9 C4 0.8(4) . . . . ? C1 N1 C10 C12 -67.6(3) . . . . ? C3 N1 C10 C12 130.2(2) . . . . ? C1 N1 C10 C11 -135.3(2) . . . . ? C3 N1 C10 C11 62.5(3) . . . . ? N1 C10 C11 C12 108.9(2) . . . . ? C10 C11 C12 C14 130.2(3) . . . . ? C10 C11 C12 C13 -129.7(3) . . . . ? N1 C10 C12 C14 121.5(3) . . . . ? C11 C10 C12 C14 -132.4(3) . . . . ? N1 C10 C12 C11 -106.1(2) . . . . ? N1 C10 C12 C13 24.2(4) . . . . ? C11 C10 C12 C13 130.3(3) . . . . ? C11 C12 C13 C14 -132.4(3) . . . . ? C10 C12 C13 C14 129.7(3) . . . . ? C11 C12 C14 C13 130.6(4) . . . . ? C10 C12 C14 C13 -129.6(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.129 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.034 # Attachment 'amino-spiro[2.2]pentanes_09032a.cif' data_09032a _database_code_depnum_ccdc_archive 'CCDC 729830' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 09032a _chemical_melting_point ? _chemical_formula_moiety 'C20 H19 N O2' _chemical_formula_sum 'C20 H19 N O2' _chemical_formula_weight 305.36 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 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 10.3033(13) _cell_length_b 10.2448(13) _cell_length_c 15.332(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.088(2) _cell_angle_gamma 90.00 _cell_volume 1612.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2860 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 27.18 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9645 _exptl_absorpt_correction_T_max 0.9645 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details 'R. Hayashi - Prof. R. Hsung / U. Wisconsin' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19028 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3678 _reflns_number_gt 2869 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0484P)^2^+0.5826P] 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 3678 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.63101(11) 0.75692(14) 0.48736(8) 0.0632(4) Uani 1 1 d . . . O2 O 0.65409(12) 0.91979(14) 0.58634(9) 0.0666(4) Uani 1 1 d . . . N1 N 0.46752(11) 0.81325(11) 0.57230(7) 0.0342(3) Uani 1 1 d . . . C1 C 0.58619(15) 0.82184(16) 0.54299(10) 0.0447(4) Uani 1 1 d . . . C2 C 0.5803(2) 0.9674(2) 0.65454(13) 0.0709(6) Uani 1 1 d . . . H2A H 0.5753 1.0639 0.6526 0.085 Uiso 1 1 calc R . . H2B H 0.6217 0.9408 0.7126 0.085 Uiso 1 1 calc R . . C3 C 0.44792(17) 0.90951(15) 0.63915(11) 0.0491(4) Uani 1 1 d . . . H3A H 0.4203 0.8682 0.6929 0.059 Uiso 1 1 calc R . . H3B H 0.3826 0.9757 0.6178 0.059 Uiso 1 1 calc R . . C4 C 0.37361(12) 0.71553(13) 0.54308(8) 0.0303(3) Uani 1 1 d . . . C5 C 0.32554(14) 0.71654(14) 0.44939(9) 0.0360(3) Uani 1 1 d . . . C6 C 0.35051(18) 0.69001(15) 0.36914(9) 0.0468(4) Uani 1 1 d . . . H6A H 0.2874 0.7083 0.3218 0.056 Uiso 1 1 calc R . . H6B H 0.4318 0.6524 0.3582 0.056 Uiso 1 1 calc R . . C7 C 0.23703(14) 0.76725(15) 0.51139(8) 0.0379(3) Uani 1 1 d . . . H7A H 0.1608 0.7133 0.5231 0.046 Uiso 1 1 calc R . . H7B H 0.2225 0.8627 0.5129 0.046 Uiso 1 1 calc R . . C8 C 0.38864(14) 0.58546(13) 0.59054(8) 0.0336(3) Uani 1 1 d . . . H8A H 0.4678 0.5411 0.5732 0.040 Uiso 1 1 calc R . . H8B H 0.3128 0.5295 0.5720 0.040 Uiso 1 1 calc R . . C9 C 0.39889(14) 0.59955(12) 0.68958(8) 0.0327(3) Uani 1 1 d . . . C10 C 0.52237(15) 0.59621(14) 0.73481(9) 0.0404(3) Uani 1 1 d . . . H10A H 0.5960 0.5791 0.7035 0.048 Uiso 1 1 calc R . . C11 C 0.54032(17) 0.61721(16) 0.82456(10) 0.0482(4) Uani 1 1 d . . . H11A H 0.6251 0.6122 0.8543 0.058 Uiso 1 1 calc R . . C12 C 0.43447(17) 0.64530(16) 0.87026(9) 0.0484(4) Uani 1 1 d . . . H12A H 0.4462 0.6613 0.9315 0.058 Uiso 1 1 calc R . . C13 C 0.31109(16) 0.65011(14) 0.82679(9) 0.0409(3) Uani 1 1 d . . . H13A H 0.2387 0.6706 0.8586 0.049 Uiso 1 1 calc R . . C14 C 0.29074(14) 0.62538(12) 0.73665(8) 0.0336(3) Uani 1 1 d . . . C15 C 0.15483(14) 0.62833(13) 0.69419(8) 0.0353(3) Uani 1 1 d . . . C16 C 0.07902(15) 0.74069(15) 0.69511(10) 0.0440(4) Uani 1 1 d . . . H16A H 0.1136 0.8164 0.7245 0.053 Uiso 1 1 calc R . . C17 C -0.04621(17) 0.74367(18) 0.65376(11) 0.0532(4) Uani 1 1 d . . . H17A H -0.0962 0.8216 0.6540 0.064 Uiso 1 1 calc R . . C18 C -0.09859(17) 0.6333(2) 0.61211(11) 0.0551(4) Uani 1 1 d . . . H18A H -0.1841 0.6354 0.5833 0.066 Uiso 1 1 calc R . . C19 C -0.02572(16) 0.52000(17) 0.61272(10) 0.0495(4) Uani 1 1 d . . . H19A H -0.0622 0.4435 0.5855 0.059 Uiso 1 1 calc R . . C20 C 0.10011(15) 0.51716(14) 0.65277(9) 0.0394(3) Uani 1 1 d . . . H20A H 0.1497 0.4390 0.6521 0.047 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 0.0467(7) 0.0879(10) 0.0577(7) -0.0030(7) 0.0209(6) 0.0020(6) O2 0.0571(7) 0.0748(9) 0.0679(8) 0.0017(7) 0.0055(6) -0.0297(7) N1 0.0386(6) 0.0323(6) 0.0321(6) -0.0014(4) 0.0057(5) -0.0015(5) C1 0.0407(8) 0.0515(9) 0.0421(8) 0.0087(7) 0.0047(6) -0.0039(7) C2 0.0905(15) 0.0653(12) 0.0575(11) -0.0123(9) 0.0103(10) -0.0366(11) C3 0.0601(10) 0.0347(8) 0.0523(9) -0.0137(7) 0.0045(7) -0.0001(7) C4 0.0345(7) 0.0313(6) 0.0257(6) -0.0012(5) 0.0056(5) 0.0024(5) C5 0.0447(8) 0.0345(7) 0.0289(6) 0.0014(5) 0.0032(5) 0.0008(6) C6 0.0670(10) 0.0413(8) 0.0322(7) -0.0005(6) 0.0049(7) 0.0060(7) C7 0.0374(7) 0.0467(8) 0.0294(6) 0.0012(6) 0.0009(5) 0.0059(6) C8 0.0446(7) 0.0294(6) 0.0272(6) -0.0029(5) 0.0062(5) 0.0009(5) C9 0.0457(8) 0.0255(6) 0.0270(6) -0.0004(5) 0.0029(5) -0.0038(5) C10 0.0459(8) 0.0376(7) 0.0372(7) -0.0014(6) 0.0015(6) -0.0024(6) C11 0.0538(9) 0.0492(9) 0.0392(8) -0.0015(7) -0.0086(7) -0.0101(7) C12 0.0673(10) 0.0489(9) 0.0282(7) -0.0039(6) -0.0012(7) -0.0176(8) C13 0.0566(9) 0.0374(7) 0.0298(7) -0.0048(6) 0.0099(6) -0.0140(6) C14 0.0468(8) 0.0260(6) 0.0283(6) -0.0011(5) 0.0051(5) -0.0082(5) C15 0.0447(8) 0.0357(7) 0.0266(6) -0.0004(5) 0.0097(5) -0.0060(6) C16 0.0515(9) 0.0412(8) 0.0410(8) -0.0070(6) 0.0144(7) -0.0017(7) C17 0.0521(10) 0.0570(10) 0.0522(9) -0.0003(8) 0.0140(8) 0.0106(8) C18 0.0439(9) 0.0753(12) 0.0458(9) -0.0006(8) 0.0023(7) 0.0008(8) C19 0.0532(9) 0.0550(10) 0.0398(8) -0.0057(7) 0.0016(7) -0.0129(8) C20 0.0493(8) 0.0361(7) 0.0328(7) -0.0001(6) 0.0041(6) -0.0064(6) _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 C1 1.205(2) . ? O2 C1 1.362(2) . ? O2 C2 1.432(2) . ? N1 C1 1.3424(19) . ? N1 C4 1.4361(17) . ? N1 C3 1.4493(18) . ? C2 C3 1.487(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.4772(18) . ? C4 C8 1.5196(18) . ? C4 C7 1.5414(18) . ? C5 C6 1.308(2) . ? C5 C7 1.4693(19) . ? C6 H6A 0.9500 . ? C6 H6B 0.9500 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5196(17) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.394(2) . ? C9 C14 1.4054(19) . ? C10 C11 1.389(2) . ? C10 H10A 0.9500 . ? C11 C12 1.378(2) . ? C11 H11A 0.9500 . ? C12 C13 1.383(2) . ? C12 H12A 0.9500 . ? C13 C14 1.4024(18) . ? C13 H13A 0.9500 . ? C14 C15 1.491(2) . ? C15 C16 1.392(2) . ? C15 C20 1.3982(19) . ? C16 C17 1.387(2) . ? C16 H16A 0.9500 . ? C17 C18 1.385(3) . ? C17 H17A 0.9500 . ? C18 C19 1.382(3) . ? C18 H18A 0.9500 . ? C19 C20 1.385(2) . ? C19 H19A 0.9500 . ? C20 H20A 0.9500 . ? 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 C1 O2 C2 108.93(13) . . ? C1 N1 C4 123.35(12) . . ? C1 N1 C3 112.36(13) . . ? C4 N1 C3 124.24(11) . . ? O1 C1 N1 128.18(15) . . ? O1 C1 O2 122.63(15) . . ? N1 C1 O2 109.18(14) . . ? O2 C2 C3 106.68(14) . . ? O2 C2 H2A 110.4 . . ? C3 C2 H2A 110.4 . . ? O2 C2 H2B 110.4 . . ? C3 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? N1 C3 C2 101.55(14) . . ? N1 C3 H3A 111.5 . . ? C2 C3 H3A 111.5 . . ? N1 C3 H3B 111.5 . . ? C2 C3 H3B 111.5 . . ? H3A C3 H3B 109.3 . . ? N1 C4 C5 117.19(11) . . ? N1 C4 C8 115.13(11) . . ? C5 C4 C8 118.88(11) . . ? N1 C4 C7 115.45(11) . . ? C5 C4 C7 58.21(9) . . ? C8 C4 C7 120.25(12) . . ? C6 C5 C7 150.15(15) . . ? C6 C5 C4 146.76(15) . . ? C7 C5 C4 63.08(9) . . ? C5 C6 H6A 120.0 . . ? C5 C6 H6B 120.0 . . ? H6A C6 H6B 120.0 . . ? C5 C7 C4 58.71(9) . . ? C5 C7 H7A 117.9 . . ? C4 C7 H7A 117.9 . . ? C5 C7 H7B 117.9 . . ? C4 C7 H7B 117.9 . . ? H7A C7 H7B 115.1 . . ? C4 C8 C9 112.98(10) . . ? C4 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? C4 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C14 118.64(12) . . ? C10 C9 C8 118.30(12) . . ? C14 C9 C8 122.89(12) . . ? C11 C10 C9 121.63(14) . . ? C11 C10 H10A 119.2 . . ? C9 C10 H10A 119.2 . . ? C12 C11 C10 119.62(15) . . ? C12 C11 H11A 120.2 . . ? C10 C11 H11A 120.2 . . ? C11 C12 C13 119.85(13) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C12 C13 C14 121.28(14) . . ? C12 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? C13 C14 C9 118.94(13) . . ? C13 C14 C15 118.63(12) . . ? C9 C14 C15 122.43(11) . . ? C16 C15 C20 118.31(14) . . ? C16 C15 C14 121.23(13) . . ? C20 C15 C14 120.46(13) . . ? C17 C16 C15 120.92(15) . . ? C17 C16 H16A 119.5 . . ? C15 C16 H16A 119.5 . . ? C16 C17 C18 120.11(16) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? C19 C18 C17 119.58(16) . . ? C19 C18 H18A 120.2 . . ? C17 C18 H18A 120.2 . . ? C18 C19 C20 120.49(15) . . ? C18 C19 H19A 119.8 . . ? C20 C19 H19A 119.8 . . ? C19 C20 C15 120.54(15) . . ? C19 C20 H20A 119.7 . . ? C15 C20 H20A 119.7 . . ? 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 C4 N1 C1 O1 3.5(2) . . . . ? C3 N1 C1 O1 -179.19(17) . . . . ? C4 N1 C1 O2 -176.89(12) . . . . ? C3 N1 C1 O2 0.48(18) . . . . ? C2 O2 C1 O1 -173.41(17) . . . . ? C2 O2 C1 N1 6.90(19) . . . . ? C1 O2 C2 C3 -11.3(2) . . . . ? C1 N1 C3 C2 -7.13(18) . . . . ? C4 N1 C3 C2 170.21(14) . . . . ? O2 C2 C3 N1 10.7(2) . . . . ? C1 N1 C4 C5 -62.74(18) . . . . ? C3 N1 C4 C5 120.21(14) . . . . ? C1 N1 C4 C8 84.47(15) . . . . ? C3 N1 C4 C8 -92.58(16) . . . . ? C1 N1 C4 C7 -128.45(14) . . . . ? C3 N1 C4 C7 54.50(17) . . . . ? N1 C4 C5 C6 74.9(3) . . . . ? C8 C4 C5 C6 -71.1(3) . . . . ? C7 C4 C5 C6 179.4(3) . . . . ? N1 C4 C5 C7 -104.47(13) . . . . ? C8 C4 C5 C7 109.58(14) . . . . ? C6 C5 C7 C4 -179.3(3) . . . . ? N1 C4 C7 C5 107.48(12) . . . . ? C8 C4 C7 C5 -107.24(13) . . . . ? N1 C4 C8 C9 50.61(15) . . . . ? C5 C4 C8 C9 -162.76(12) . . . . ? C7 C4 C8 C9 -94.77(14) . . . . ? C4 C8 C9 C10 -98.83(14) . . . . ? C4 C8 C9 C14 76.31(16) . . . . ? C14 C9 C10 C11 0.2(2) . . . . ? C8 C9 C10 C11 175.59(13) . . . . ? C9 C10 C11 C12 -1.6(2) . . . . ? C10 C11 C12 C13 1.1(2) . . . . ? C11 C12 C13 C14 0.7(2) . . . . ? C12 C13 C14 C9 -2.1(2) . . . . ? C12 C13 C14 C15 178.25(13) . . . . ? C10 C9 C14 C13 1.61(19) . . . . ? C8 C9 C14 C13 -173.52(12) . . . . ? C10 C9 C14 C15 -178.78(12) . . . . ? C8 C9 C14 C15 6.09(19) . . . . ? C13 C14 C15 C16 60.22(18) . . . . ? C9 C14 C15 C16 -119.39(15) . . . . ? C13 C14 C15 C20 -119.35(14) . . . . ? C9 C14 C15 C20 61.04(18) . . . . ? C20 C15 C16 C17 -1.9(2) . . . . ? C14 C15 C16 C17 178.50(13) . . . . ? C15 C16 C17 C18 1.2(2) . . . . ? C16 C17 C18 C19 0.6(3) . . . . ? C17 C18 C19 C20 -1.6(2) . . . . ? C18 C19 C20 C15 0.8(2) . . . . ? C16 C15 C20 C19 0.9(2) . . . . ? C14 C15 C20 C19 -179.50(13) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.242 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.034 # Attachment 'amino-spiro[2.2]pentanes_09058a.cif' data_09058a _database_code_depnum_ccdc_archive 'CCDC 729831' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 09058a _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 N O2' _chemical_formula_sum 'C18 H23 N O2' _chemical_formula_weight 285.37 _chemical_absolute_configuration rm 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.2307(11) _cell_length_b 16.094(3) _cell_length_c 8.0544(15) _cell_angle_alpha 90.00 _cell_angle_beta 96.906(2) _cell_angle_gamma 90.00 _cell_volume 801.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2971 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 26.38 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9738 _exptl_absorpt_correction_T_max 0.9812 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2009)' _exptl_special_details 'T. Lu / Prof. R. Hsung - U. Wisconsin' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6605 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 26.41 _reflns_number_total 1704 _reflns_number_gt 1515 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0428P)^2^+0.1053P] 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 0.1(15) _refine_ls_number_reflns 1704 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0861 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.0021(2) 0.64510(11) 0.9102(2) 0.0392(4) Uani 1 1 d . . . O2 O 0.2814(3) 0.69576(10) 1.08305(18) 0.0364(4) Uani 1 1 d . . . N1 N 0.3176(3) 0.68794(11) 0.8127(2) 0.0261(4) Uani 1 1 d . . . C1 C 0.1828(4) 0.67286(13) 0.9292(3) 0.0285(5) Uani 1 1 d . . . C2 C 0.5083(4) 0.70870(16) 1.0704(3) 0.0367(5) Uani 1 1 d . . . H2A H 0.5933 0.6586 1.1070 0.044 Uiso 1 1 calc R . . H2B H 0.5645 0.7564 1.1401 0.044 Uiso 1 1 calc R . . C3 C 0.5199(3) 0.72634(12) 0.8848(3) 0.0270(5) Uani 1 1 d . . . H3A H 0.6454 0.6962 0.8465 0.032 Uiso 1 1 calc R . . C4 C 0.5370(4) 0.81859(13) 0.8494(3) 0.0299(5) Uani 1 1 d . . . C5 C 0.3618(4) 0.86665(15) 0.7875(3) 0.0418(6) Uani 1 1 d . . . H5A H 0.2238 0.8417 0.7607 0.050 Uiso 1 1 calc R . . C6 C 0.3877(5) 0.95167(17) 0.7644(4) 0.0554(8) Uani 1 1 d . . . H6A H 0.2670 0.9847 0.7221 0.067 Uiso 1 1 calc R . . C7 C 0.5881(6) 0.98806(17) 0.8027(4) 0.0552(8) Uani 1 1 d . . . H7A H 0.6053 1.0460 0.7863 0.066 Uiso 1 1 calc R . . C8 C 0.7620(5) 0.94082(17) 0.8644(4) 0.0526(7) Uani 1 1 d . . . H8A H 0.8997 0.9660 0.8914 0.063 Uiso 1 1 calc R . . C9 C 0.7374(4) 0.85631(15) 0.8874(3) 0.0406(6) Uani 1 1 d . . . H9A H 0.8589 0.8237 0.9297 0.049 Uiso 1 1 calc R . . C10 C 0.2833(3) 0.64949(14) 0.6486(3) 0.0283(5) Uani 1 1 d . . . C11 C 0.3651(3) 0.69858(16) 0.5071(3) 0.0331(5) Uani 1 1 d . . . H11A H 0.4323 0.7534 0.5343 0.040 Uiso 1 1 calc R . . H11B H 0.4274 0.6671 0.4187 0.040 Uiso 1 1 calc R . . C12 C 0.1302(3) 0.68965(16) 0.5180(3) 0.0339(5) Uani 1 1 d . . . C13 C -0.0643(4) 0.74278(19) 0.5073(3) 0.0457(6) Uani 1 1 d . . . H13A H -0.0616 0.7961 0.4463 0.055 Uiso 1 1 calc R . . H13B H -0.1480 0.7435 0.6043 0.055 Uiso 1 1 calc R . . C14 C -0.0628(4) 0.6622(2) 0.4061(3) 0.0492(7) Uani 1 1 d . . . H14A H -0.1454 0.6143 0.4419 0.059 Uiso 1 1 calc R . . H14B H -0.0590 0.6668 0.2839 0.059 Uiso 1 1 calc R . . C15 C 0.3043(4) 0.55616(14) 0.6501(3) 0.0341(5) Uani 1 1 d . . . H15A H 0.2611 0.5351 0.5355 0.041 Uiso 1 1 calc R . . H15B H 0.2022 0.5329 0.7231 0.041 Uiso 1 1 calc R . . C16 C 0.5293(4) 0.52473(14) 0.7101(3) 0.0370(5) Uani 1 1 d . . . H16A H 0.5714 0.5446 0.8258 0.044 Uiso 1 1 calc R . . H16B H 0.6322 0.5488 0.6387 0.044 Uiso 1 1 calc R . . C17 C 0.5488(5) 0.43058(15) 0.7072(4) 0.0444(6) Uani 1 1 d . . . H17A H 0.4529 0.4065 0.7842 0.053 Uiso 1 1 calc R . . H17B H 0.4985 0.4104 0.5931 0.053 Uiso 1 1 calc R . . C18 C 0.7759(5) 0.40032(18) 0.7572(4) 0.0600(8) Uani 1 1 d . . . H18A H 0.7763 0.3395 0.7630 0.090 Uiso 1 1 calc R . . H18B H 0.8305 0.4232 0.8670 0.090 Uiso 1 1 calc R . . H18C H 0.8687 0.4186 0.6742 0.090 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 0.0248(8) 0.0508(10) 0.0432(9) 0.0060(8) 0.0085(7) -0.0016(7) O2 0.0418(9) 0.0413(9) 0.0264(8) 0.0004(7) 0.0051(7) -0.0014(8) N1 0.0220(8) 0.0293(9) 0.0269(9) -0.0003(7) 0.0022(7) -0.0010(7) C1 0.0306(11) 0.0277(10) 0.0271(11) 0.0048(9) 0.0028(8) 0.0061(9) C2 0.0382(12) 0.0357(12) 0.0332(12) 0.0054(10) -0.0078(10) -0.0046(10) C3 0.0246(10) 0.0252(10) 0.0300(11) 0.0007(9) -0.0010(9) 0.0018(8) C4 0.0353(12) 0.0282(11) 0.0270(12) -0.0009(9) 0.0073(9) -0.0004(9) C5 0.0420(14) 0.0333(13) 0.0505(16) 0.0075(11) 0.0067(11) 0.0055(11) C6 0.069(2) 0.0372(15) 0.063(2) 0.0124(13) 0.0177(16) 0.0149(14) C7 0.091(2) 0.0277(13) 0.0522(17) -0.0014(12) 0.0291(16) -0.0087(14) C8 0.0645(18) 0.0384(14) 0.0580(18) -0.0080(13) 0.0197(14) -0.0183(13) C9 0.0407(14) 0.0355(13) 0.0463(15) -0.0035(11) 0.0074(11) -0.0059(10) C10 0.0251(10) 0.0345(11) 0.0252(11) -0.0015(9) 0.0026(8) -0.0036(9) C11 0.0259(11) 0.0457(13) 0.0273(11) 0.0034(10) 0.0021(8) -0.0003(10) C12 0.0261(11) 0.0456(13) 0.0296(11) 0.0042(10) 0.0016(9) -0.0042(10) C13 0.0248(12) 0.0685(18) 0.0429(15) 0.0135(13) 0.0003(10) 0.0047(11) C14 0.0308(12) 0.079(2) 0.0359(13) 0.0043(13) -0.0041(10) -0.0097(13) C15 0.0384(13) 0.0345(12) 0.0294(12) -0.0047(9) 0.0043(10) -0.0068(10) C16 0.0432(13) 0.0301(11) 0.0385(13) -0.0010(10) 0.0076(11) -0.0024(10) C17 0.0570(16) 0.0314(13) 0.0470(15) 0.0017(11) 0.0152(12) -0.0004(11) C18 0.0699(19) 0.0362(14) 0.076(2) 0.0027(15) 0.0158(16) 0.0132(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 C1 1.204(3) . ? O2 C1 1.366(3) . ? O2 C2 1.444(3) . ? N1 C1 1.355(3) . ? N1 C10 1.452(3) . ? N1 C3 1.460(3) . ? C2 C3 1.532(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.518(3) . ? C3 H3A 1.0000 . ? C4 C5 1.381(3) . ? C4 C9 1.389(3) . ? C5 C6 1.393(4) . ? C5 H5A 0.9500 . ? C6 C7 1.380(4) . ? C6 H6A 0.9500 . ? C7 C8 1.367(4) . ? C7 H7A 0.9500 . ? C8 C9 1.384(4) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C12 1.481(3) . ? C10 C15 1.508(3) . ? C10 C11 1.524(3) . ? C11 C12 1.483(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.477(3) . ? C12 C14 1.481(3) . ? C13 C14 1.532(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.514(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.520(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.504(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 C1 O2 C2 108.21(16) . . ? C1 N1 C10 121.25(17) . . ? C1 N1 C3 112.21(17) . . ? C10 N1 C3 124.61(17) . . ? O1 C1 N1 128.8(2) . . ? O1 C1 O2 121.8(2) . . ? N1 C1 O2 109.34(18) . . ? O2 C2 C3 104.89(16) . . ? O2 C2 H2A 110.8 . . ? C3 C2 H2A 110.8 . . ? O2 C2 H2B 110.8 . . ? C3 C2 H2B 110.8 . . ? H2A C2 H2B 108.8 . . ? N1 C3 C4 114.59(17) . . ? N1 C3 C2 99.77(17) . . ? C4 C3 C2 112.17(18) . . ? N1 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? C2 C3 H3A 110.0 . . ? C5 C4 C9 119.0(2) . . ? C5 C4 C3 123.0(2) . . ? C9 C4 C3 117.9(2) . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C8 C7 C6 120.1(3) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? C7 C8 C9 120.0(3) . . ? C7 C8 H8A 120.0 . . ? C9 C8 H8A 120.0 . . ? C8 C9 C4 120.8(3) . . ? C8 C9 H9A 119.6 . . ? C4 C9 H9A 119.6 . . ? N1 C10 C12 118.20(19) . . ? N1 C10 C15 114.48(19) . . ? C12 C10 C15 119.21(19) . . ? N1 C10 C11 115.73(19) . . ? C12 C10 C11 59.13(14) . . ? C15 C10 C11 119.07(19) . . ? C12 C11 C10 58.99(14) . . ? C12 C11 H11A 117.9 . . ? C10 C11 H11A 117.9 . . ? C12 C11 H11B 117.9 . . ? C10 C11 H11B 117.9 . . ? H11A C11 H11B 115.0 . . ? C13 C12 C14 62.40(18) . . ? C13 C12 C10 138.4(2) . . ? C14 C12 C10 135.1(2) . . ? C13 C12 C11 138.5(2) . . ? C14 C12 C11 136.7(2) . . ? C10 C12 C11 61.87(14) . . ? C12 C13 C14 58.91(16) . . ? C12 C13 H13A 117.9 . . ? C14 C13 H13A 117.9 . . ? C12 C13 H13B 117.9 . . ? C14 C13 H13B 117.9 . . ? H13A C13 H13B 115.0 . . ? C12 C14 C13 58.69(17) . . ? C12 C14 H14A 117.9 . . ? C13 C14 H14A 117.9 . . ? C12 C14 H14B 117.9 . . ? C13 C14 H14B 117.9 . . ? H14A C14 H14B 115.1 . . ? C10 C15 C16 114.28(18) . . ? C10 C15 H15A 108.7 . . ? C16 C15 H15A 108.7 . . ? C10 C15 H15B 108.7 . . ? C16 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 C17 113.6(2) . . ? C15 C16 H16A 108.8 . . ? C17 C16 H16A 108.8 . . ? C15 C16 H16B 108.8 . . ? C17 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C16 113.1(2) . . ? C18 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? C18 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C10 N1 C1 O1 -18.4(3) . . . . ? C3 N1 C1 O1 176.8(2) . . . . ? C10 N1 C1 O2 162.65(17) . . . . ? C3 N1 C1 O2 -2.2(2) . . . . ? C2 O2 C1 O1 167.5(2) . . . . ? C2 O2 C1 N1 -13.4(2) . . . . ? C1 O2 C2 C3 22.7(2) . . . . ? C1 N1 C3 C4 -104.6(2) . . . . ? C10 N1 C3 C4 91.2(2) . . . . ? C1 N1 C3 C2 15.4(2) . . . . ? C10 N1 C3 C2 -148.8(2) . . . . ? O2 C2 C3 N1 -22.2(2) . . . . ? O2 C2 C3 C4 99.6(2) . . . . ? N1 C3 C4 C5 13.8(3) . . . . ? C2 C3 C4 C5 -99.1(2) . . . . ? N1 C3 C4 C9 -168.72(19) . . . . ? C2 C3 C4 C9 78.4(3) . . . . ? C9 C4 C5 C6 -0.1(4) . . . . ? C3 C4 C5 C6 177.3(2) . . . . ? C4 C5 C6 C7 0.2(4) . . . . ? C5 C6 C7 C8 -0.3(4) . . . . ? C6 C7 C8 C9 0.4(4) . . . . ? C7 C8 C9 C4 -0.3(4) . . . . ? C5 C4 C9 C8 0.2(4) . . . . ? C3 C4 C9 C8 -177.4(2) . . . . ? C1 N1 C10 C12 84.3(3) . . . . ? C3 N1 C10 C12 -112.8(2) . . . . ? C1 N1 C10 C15 -64.2(3) . . . . ? C3 N1 C10 C15 98.7(2) . . . . ? C1 N1 C10 C11 151.48(19) . . . . ? C3 N1 C10 C11 -45.6(3) . . . . ? N1 C10 C11 C12 -108.9(2) . . . . ? C15 C10 C11 C12 108.6(2) . . . . ? N1 C10 C12 C13 -27.9(4) . . . . ? C15 C10 C12 C13 119.1(3) . . . . ? C11 C10 C12 C13 -132.6(3) . . . . ? N1 C10 C12 C14 -126.1(3) . . . . ? C15 C10 C12 C14 20.9(4) . . . . ? C11 C10 C12 C14 129.2(3) . . . . ? N1 C10 C12 C11 104.7(2) . . . . ? C15 C10 C12 C11 -108.3(2) . . . . ? C10 C11 C12 C13 132.5(3) . . . . ? C10 C11 C12 C14 -127.2(3) . . . . ? C10 C12 C13 C14 -128.0(3) . . . . ? C11 C12 C13 C14 130.4(3) . . . . ? C10 C12 C14 C13 132.1(3) . . . . ? C11 C12 C14 C13 -132.6(3) . . . . ? N1 C10 C15 C16 -65.2(3) . . . . ? C12 C10 C15 C16 146.6(2) . . . . ? C11 C10 C15 C16 77.8(3) . . . . ? C10 C15 C16 C17 -178.7(2) . . . . ? C15 C16 C17 C18 176.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.139 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.031