# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Blake, Alexander J.' 'Clark, J. Stephen' 'Cooke, Paul A.' 'Goldsmith, Michael D.' 'Hodgson, Paul B.' 'Street, Leslie J.' _publ_contact_author_name 'Dr J. Stephen Clark' _publ_contact_author_address ; School of Chemistry University of Nottingham University Park NOTTINGHAM NG7 2RD UK ; _publ_contact_author_email 'J.S.CLARK@NOTTINGHAM.AC.UK' _publ_section_title ; Rearrangement of ammonium ylides produced by intramolecular reaction of catalytically generated metal carbenoids. Part 2. Stereoselective synthesis of bicyclic amines ; data_alcohol-22 _database_code_CSD 172675 # Code 25NOHR _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C10 H17 N O' _chemical_formula_sum 'C10 H17 N O' _chemical_formula_weight 167.25 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' 'O' 'O' 0.0106 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.536(2) _cell_length_b 11.150(3) _cell_length_c 10.547(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.40(2) _cell_angle_gamma 90.00 _cell_volume 967.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 12 _cell_measurement_theta_max 24.5 _exptl_crystal_description trapezoid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Stoe Stadi-4 four-circle' _diffrn_measurement_method 'omega-theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 'random variation +/-3.2' _diffrn_reflns_number 2067 _diffrn_reflns_av_R_equivalents 0.092 _diffrn_reflns_av_sigmaI/netI 0.045 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 24.96 _reflns_number_total 1702 _reflns_number_gt 1258 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STADI4 v1.07 (Stoe, 1997)' _computing_cell_refinement 'STADI4 v1.07' _computing_data_reduction 'XRED v1.09 (Stoe, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v5.03 (Sheldrick, 1994)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.042P)^2^+0.901P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary 'Fourier difference syntheses' _atom_sites_solution_hydrogens 'constrained to idealised geometry' _refine_ls_hydrogen_treatment 'all riding except hydroxyl (rotating)' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1702 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1407 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5238(2) 0.68269(16) 1.08655(16) 0.0351(5) Uani 1 d . . . H1 H 0.5499 0.7364 1.1442 0.053 Uiso 1 calc R . . N1 N 0.6207(2) 0.64219(18) 0.77553(18) 0.0257(5) Uani 1 d . . . C2 C 0.5119(3) 0.6282(2) 0.8643(2) 0.0267(6) Uani 1 d . . . H2 H 0.5188 0.5439 0.8977 0.032 Uiso 1 calc R . . C3 C 0.5843(3) 0.7127(2) 0.9780(2) 0.0288(6) Uani 1 d . . . H3 H 0.5552 0.7975 0.9507 0.035 Uiso 1 calc R . . C4 C 0.7658(3) 0.6933(3) 0.9985(2) 0.0345(7) Uani 1 d . . . H4A H 0.8020 0.6178 1.0468 0.041 Uiso 1 calc R . . H4B H 0.8292 0.7610 1.0474 0.041 Uiso 1 calc R . . C5 C 0.7835(3) 0.6868(2) 0.8587(2) 0.0298(6) Uani 1 d . . . H5 H 0.8066 0.7684 0.8286 0.036 Uiso 1 calc R . . C6 C 0.9092(3) 0.5965(3) 0.8361(3) 0.0362(7) Uani 1 d . . . H6A H 0.9545 0.6228 0.7634 0.043 Uiso 1 calc R . . H6B H 0.9992 0.5860 0.9167 0.043 Uiso 1 calc R . . C7 C 0.8121(3) 0.4813(3) 0.8007(3) 0.0376(7) Uani 1 d . . . H7A H 0.8650 0.4255 0.7519 0.045 Uiso 1 calc R . . H7B H 0.7975 0.4404 0.8801 0.045 Uiso 1 calc R . . C8 C 0.6511(3) 0.5269(2) 0.7144(2) 0.0309(6) Uani 1 d . . . H8A H 0.6581 0.5402 0.6232 0.037 Uiso 1 calc R . . H8B H 0.5629 0.4687 0.7127 0.037 Uiso 1 calc R . . C9 C 0.3359(3) 0.6576(2) 0.7946(2) 0.0327(6) Uani 1 d . . . H9A H 0.2731 0.6617 0.8610 0.039 Uiso 1 calc R . . H9B H 0.3322 0.7381 0.7542 0.039 Uiso 1 calc R . . C10 C 0.2547(3) 0.5703(3) 0.6903(3) 0.0397(7) Uani 1 d . . . H10 H 0.2464 0.4896 0.7165 0.048 Uiso 1 calc R . . C11 C 0.1938(4) 0.5962(3) 0.5654(3) 0.0523(9) Uani 1 d . . . H11A H 0.1996 0.6759 0.5352 0.063 Uiso 1 calc R . . H11B H 0.1439 0.5352 0.5053 0.063 Uiso 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 0.0495(12) 0.0341(11) 0.0261(9) -0.0055(8) 0.0178(9) -0.0068(9) N1 0.0263(11) 0.0293(12) 0.0221(10) -0.0017(8) 0.0076(8) -0.0012(9) C2 0.0317(14) 0.0273(13) 0.0229(12) 0.0001(10) 0.0105(11) -0.0017(11) C3 0.0347(14) 0.0286(14) 0.0253(12) -0.0006(10) 0.0114(11) -0.0011(11) C4 0.0339(15) 0.0387(16) 0.0279(13) -0.0046(11) 0.0033(11) -0.0008(12) C5 0.0262(13) 0.0326(14) 0.0309(13) 0.0016(11) 0.0080(11) -0.0030(11) C6 0.0274(14) 0.0470(17) 0.0341(14) 0.0040(12) 0.0078(11) 0.0047(12) C7 0.0359(15) 0.0410(16) 0.0359(15) -0.0004(12) 0.0096(12) 0.0105(13) C8 0.0342(14) 0.0316(14) 0.0273(13) -0.0031(11) 0.0091(11) 0.0037(12) C9 0.0287(14) 0.0406(16) 0.0313(13) -0.0043(12) 0.0122(11) -0.0028(12) C10 0.0305(15) 0.0487(18) 0.0418(16) -0.0115(13) 0.0127(12) -0.0084(13) C11 0.0383(17) 0.078(2) 0.0406(17) -0.0126(16) 0.0118(14) -0.0069(16) _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 C3 1.415(3) . ? N1 C8 1.492(3) . ? N1 C2 1.492(3) . ? N1 C5 1.517(3) . ? C2 C3 1.521(3) . ? C2 C9 1.522(3) . ? C3 C4 1.522(4) . ? C4 C5 1.523(3) . ? C5 C6 1.535(4) . ? C6 C7 1.521(4) . ? C7 C8 1.520(4) . ? C9 C10 1.494(4) . ? C10 C11 1.313(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C2 112.97(19) . . ? C8 N1 C5 107.13(18) . . ? C2 N1 C5 107.38(17) . . ? N1 C2 C3 103.88(19) . . ? N1 C2 C9 111.89(19) . . ? C3 C2 C9 112.9(2) . . ? O1 C3 C2 109.4(2) . . ? O1 C3 C4 115.4(2) . . ? C2 C3 C4 102.04(19) . . ? C3 C4 C5 103.21(19) . . ? N1 C5 C4 105.32(19) . . ? N1 C5 C6 105.4(2) . . ? C4 C5 C6 115.8(2) . . ? C7 C6 C5 103.5(2) . . ? C8 C7 C6 102.2(2) . . ? N1 C8 C7 105.3(2) . . ? C10 C9 C2 114.9(2) . . ? C11 C10 C9 125.3(3) . . ? 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 C8 N1 C2 C3 141.6(2) . . . . ? C5 N1 C2 C3 23.7(2) . . . . ? C8 N1 C2 C9 -96.3(2) . . . . ? C5 N1 C2 C9 145.8(2) . . . . ? N1 C2 C3 O1 -162.72(19) . . . . ? C9 C2 C3 O1 75.8(3) . . . . ? N1 C2 C3 C4 -40.1(2) . . . . ? C9 C2 C3 C4 -161.5(2) . . . . ? O1 C3 C4 C5 159.7(2) . . . . ? C2 C3 C4 C5 41.2(2) . . . . ? C8 N1 C5 C4 -119.6(2) . . . . ? C2 N1 C5 C4 2.0(3) . . . . ? C8 N1 C5 C6 3.3(2) . . . . ? C2 N1 C5 C6 124.9(2) . . . . ? C3 C4 C5 N1 -26.9(3) . . . . ? C3 C4 C5 C6 -142.9(2) . . . . ? N1 C5 C6 C7 -26.7(2) . . . . ? C4 C5 C6 C7 89.2(3) . . . . ? C5 C6 C7 C8 39.5(2) . . . . ? C2 N1 C8 C7 -96.5(2) . . . . ? C5 N1 C8 C7 21.5(2) . . . . ? C6 C7 C8 N1 -37.9(2) . . . . ? N1 C2 C9 C10 68.7(3) . . . . ? C3 C2 C9 C10 -174.6(2) . . . . ? C2 C9 C10 C11 -119.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.19 _refine_diff_density_min -0.22 _refine_diff_density_rms 0.05 #===END data_alcohol-23 _database_code_CSD 172676 #Code S251 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H19 N O' _chemical_formula_sum 'C11 H19 N O' _chemical_formula_weight 181.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 18.996(2) _cell_length_b 8.413(3) _cell_length_c 6.982(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1115.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.079 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.530 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4RA' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 1373 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_av_sigmaI/netI 0.059 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 50.35 _reflns_number_total 637 _reflns_number_gt 543 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.075P)^2^+0.046P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens 'OH from difference Fourier synthesis, others placed geometrically' _refine_ls_hydrogen_treatment 'rigid group and riding model, respectively' _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 'not reliably determined' _refine_ls_number_reflns 637 _refine_ls_number_parameters 116 _refine_ls_number_restraints 35 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1410 _refine_ls_wR_factor_gt 0.1345 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _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 N1 N 0.10787(18) 0.3600(6) 0.1815(7) 0.0582(12) Uani 1 1 d U . . C2 C 0.1205(3) 0.4708(7) 0.3398(9) 0.0638(14) Uani 1 1 d U . . H2 H 0.1616 0.4331 0.4116 0.077 Uiso 1 1 calc R . . O3 O 0.0031(2) 0.5601(5) 0.4135(6) 0.0803(13) Uani 1 1 d U . . H3O H -0.0262 0.5666 0.4994 0.120 Uiso 1 1 calc R . . C3 C 0.0554(3) 0.4477(6) 0.4652(8) 0.0670(15) Uani 1 1 d U . . H3 H 0.0677 0.4585 0.6009 0.080 Uiso 1 1 calc R . . C4 C 0.0325(3) 0.2780(7) 0.4209(7) 0.0772(17) Uani 1 1 d U . . H4A H -0.0144 0.2770 0.3658 0.093 Uiso 1 1 calc R . . H4B H 0.0322 0.2142 0.5366 0.093 Uiso 1 1 calc R . . C5 C 0.0863(2) 0.2139(7) 0.2780(9) 0.0640(14) Uani 1 1 d U . . H5 H 0.1267 0.1734 0.3504 0.077 Uiso 1 1 calc R . . C6 C 0.0633(3) 0.0881(7) 0.1425(12) 0.0784(16) Uani 1 1 d U . . H6A H 0.0216 0.1231 0.0742 0.094 Uiso 1 1 calc R . . H6B H 0.0515 -0.0076 0.2128 0.094 Uiso 1 1 calc R . . C7 C 0.1211(3) 0.0531(7) 0.0023(11) 0.092(2) Uani 1 1 d U . . H7A H 0.1596 0.0007 0.0684 0.110 Uiso 1 1 calc R . . H7B H 0.1037 -0.0190 -0.0952 0.110 Uiso 1 1 calc R . . C8 C 0.1478(3) 0.2003(9) -0.0909(10) 0.095(2) Uani 1 1 d U . . H8A H 0.1119 0.2419 -0.1761 0.114 Uiso 1 1 calc R . . H8B H 0.1889 0.1746 -0.1674 0.114 Uiso 1 1 calc R . . C9 C 0.1674(3) 0.3279(9) 0.0561(10) 0.0806(17) Uani 1 1 d U . . H9A H 0.2072 0.2920 0.1317 0.097 Uiso 1 1 calc R . . H9B H 0.1811 0.4247 -0.0097 0.097 Uiso 1 1 calc R . . C10 C 0.1349(3) 0.6392(7) 0.2760(9) 0.0773(17) Uani 1 1 d U . . H10A H 0.1772 0.6412 0.1983 0.093 Uiso 1 1 calc R . . H10B H 0.0961 0.6764 0.1978 0.093 Uiso 1 1 calc R . . C11 C 0.1440(4) 0.7472(7) 0.4431(9) 0.106(2) Uani 1 1 d DU . . H11 H 0.1060 0.7565 0.5266 0.127 Uiso 1 1 calc R . . C12 C 0.2002(4) 0.8303(7) 0.4837(9) 0.155(4) Uani 1 1 d DU . . H12A H 0.2395 0.8249 0.4044 0.186 Uiso 1 1 calc R . . H12B H 0.2009 0.8948 0.5918 0.186 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 N1 0.046(2) 0.075(3) 0.053(2) 0.005(2) 0.001(2) 0.001(2) C2 0.058(3) 0.075(4) 0.058(3) 0.000(3) -0.008(3) 0.000(3) O3 0.085(2) 0.103(3) 0.053(2) 0.003(2) 0.0133(19) 0.024(2) C3 0.074(3) 0.086(4) 0.041(3) 0.006(3) -0.001(3) 0.001(3) C4 0.090(3) 0.085(4) 0.057(4) 0.010(3) 0.018(3) -0.008(3) C5 0.057(2) 0.066(3) 0.069(4) 0.010(3) -0.001(3) 0.002(3) C6 0.076(3) 0.074(3) 0.085(4) -0.007(4) 0.003(3) 0.001(3) C7 0.092(4) 0.085(4) 0.098(6) -0.022(4) 0.005(4) 0.010(3) C8 0.081(4) 0.113(5) 0.091(6) -0.016(4) 0.024(4) 0.017(4) C9 0.067(3) 0.093(4) 0.082(4) 0.000(4) 0.016(3) -0.003(3) C10 0.083(3) 0.081(4) 0.068(4) 0.005(4) -0.012(4) -0.010(3) C11 0.117(5) 0.102(5) 0.098(6) -0.002(5) -0.016(5) -0.015(4) C12 0.167(6) 0.180(10) 0.118(8) 0.002(8) -0.035(7) -0.060(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C9 1.456(7) . ? N1 C5 1.461(7) . ? N1 C2 1.466(8) . ? C2 C10 1.510(8) . ? C2 C3 1.527(8) . ? O3 C3 1.419(6) . ? C3 C4 1.524(7) . ? C4 C5 1.527(7) . ? C5 C6 1.485(8) . ? C6 C7 1.500(9) . ? C7 C8 1.488(8) . ? C8 C9 1.531(9) . ? C10 C11 1.489(8) . ? C11 C12 1.308(10) . ? 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 C9 N1 C5 109.8(5) . . ? C9 N1 C2 116.4(4) . . ? C5 N1 C2 103.5(4) . . ? N1 C2 C10 113.8(5) . . ? N1 C2 C3 102.6(4) . . ? C10 C2 C3 115.8(5) . . ? O3 C3 C4 111.8(5) . . ? O3 C3 C2 109.7(4) . . ? C4 C3 C2 103.6(5) . . ? C3 C4 C5 105.8(4) . . ? N1 C5 C6 112.8(5) . . ? N1 C5 C4 101.1(4) . . ? C6 C5 C4 118.2(4) . . ? C5 C6 C7 109.9(5) . . ? C8 C7 C6 111.8(5) . . ? C7 C8 C9 111.9(5) . . ? N1 C9 C8 110.1(5) . . ? C11 C10 C2 111.2(5) . . ? C12 C11 C10 126.2(4) . . ? 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 C9 N1 C2 C10 66.8(6) . . . . ? C5 N1 C2 C10 -172.7(4) . . . . ? C9 N1 C2 C3 -167.3(5) . . . . ? C5 N1 C2 C3 -46.8(5) . . . . ? N1 C2 C3 O3 -92.7(5) . . . . ? C10 C2 C3 O3 31.9(7) . . . . ? N1 C2 C3 C4 26.8(5) . . . . ? C10 C2 C3 C4 151.4(5) . . . . ? O3 C3 C4 C5 119.3(5) . . . . ? C2 C3 C4 C5 1.3(5) . . . . ? C9 N1 C5 C6 -61.1(6) . . . . ? C2 N1 C5 C6 174.0(4) . . . . ? C9 N1 C5 C4 171.7(4) . . . . ? C2 N1 C5 C4 46.8(5) . . . . ? C3 C4 C5 N1 -28.8(5) . . . . ? C3 C4 C5 C6 -152.4(5) . . . . ? N1 C5 C6 C7 56.9(6) . . . . ? C4 C5 C6 C7 174.4(5) . . . . ? C5 C6 C7 C8 -51.7(7) . . . . ? C6 C7 C8 C9 51.6(7) . . . . ? C5 N1 C9 C8 58.2(6) . . . . ? C2 N1 C9 C8 175.3(5) . . . . ? C7 C8 C9 N1 -54.9(7) . . . . ? N1 C2 C10 C11 177.3(5) . . . . ? C3 C2 C10 C11 58.7(7) . . . . ? C2 C10 C11 C12 119.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3O N1 0.82 2.10 2.898(6) 165 2_565 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 50.35 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.19 _refine_diff_density_min -0.14 _refine_diff_density_rms 0.03 #===END data_alcohol-24 _database_code_CSD 172677 #Code OHENEN _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H19 N O' _chemical_formula_sum 'C11 H19 N O' _chemical_formula_weight 181.27 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 'P 1 21/n 1' 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 7.554(4) _cell_length_b 7.161(3) _cell_length_c 19.49(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.12(8) _cell_angle_gamma 90.00 _cell_volume 1037.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.160 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; There was no significant diffraction above 2theta of 45 degrees. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega/theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 'variation +-4.6' _diffrn_reflns_number 1355 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0762 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 22.52 _reflns_number_total 1355 _reflns_number_gt 850 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STADI-4 (Stoe & Cie, 1997a)' _computing_cell_refinement STADI-4 _computing_data_reduction 'X-RED (Stoe & Cie, 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC version 5.03 (Sheldrick, 1994)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.072P)^2^+1.50P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens 'found from delta-F synthesis' _refine_ls_hydrogen_treatment 'idealised and riding model used (except O-H - rigid rotating group)' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1355 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1263 _refine_ls_R_factor_gt 0.0750 _refine_ls_wR_factor_ref 0.1988 _refine_ls_wR_factor_gt 0.1587 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.001 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.9126(5) 0.1420(5) 0.86369(19) 0.0268(10) Uani 1 1 d . . . C2 C 0.8325(6) -0.0452(6) 0.8704(3) 0.0279(12) Uani 1 1 d . . . H2 H 0.9021 -0.1064 0.9128 0.033 Uiso 1 1 calc R . . C3 C 0.8511(6) -0.1657(7) 0.8077(2) 0.0304(12) Uani 1 1 d . . . H3 H 0.8132 -0.2957 0.8171 0.036 Uiso 1 1 calc R . . O3 O 0.7332(5) -0.0970(5) 0.74791(19) 0.0404(10) Uani 1 1 d . . . H3O H 0.7155 -0.1808 0.7173 0.061 Uiso 1 1 calc R . . C4 C 1.0444(7) -0.1725(7) 0.7949(3) 0.0363(13) Uani 1 1 d . . . H4A H 1.0471 -0.2356 0.7499 0.044 Uiso 1 1 calc R . . H4B H 1.1183 -0.2469 0.8322 0.044 Uiso 1 1 calc R . . C5 C 1.1258(7) 0.0233(7) 0.7934(3) 0.0341(13) Uani 1 1 d . . . H5A H 1.2548 0.0135 0.7901 0.041 Uiso 1 1 calc R . . H5B H 1.0638 0.0925 0.7522 0.041 Uiso 1 1 calc R . . C6 C 1.1053(6) 0.1256(7) 0.8585(2) 0.0298(12) Uani 1 1 d . . . H6 H 1.1684 0.0538 0.8997 0.036 Uiso 1 1 calc R . . C7 C 1.1659(7) 0.3268(7) 0.8657(3) 0.0338(13) Uani 1 1 d . . . H7A H 1.1317 0.3947 0.8211 0.041 Uiso 1 1 calc R . . H7B H 1.2978 0.3353 0.8809 0.041 Uiso 1 1 calc R . . C8 C 1.0661(7) 0.4046(7) 0.9215(3) 0.0369(14) Uani 1 1 d . . . H8A H 1.0197 0.5316 0.9089 0.044 Uiso 1 1 calc R . . H8B H 1.1464 0.4098 0.9674 0.044 Uiso 1 1 calc R . . C9 C 0.9097(7) 0.2663(7) 0.9231(2) 0.0373(14) Uani 1 1 d . . . H9A H 0.9284 0.1950 0.9673 0.045 Uiso 1 1 calc R . . H9B H 0.7935 0.3333 0.9181 0.045 Uiso 1 1 calc R . . C10 C 0.6382(7) -0.0268(8) 0.8809(3) 0.0425(15) Uani 1 1 d . . . H10A H 0.6347 0.0548 0.9217 0.051 Uiso 1 1 calc R . . H10B H 0.5678 0.0351 0.8395 0.051 Uiso 1 1 calc R . . C11 C 0.5514(7) -0.2072(8) 0.8921(3) 0.0427(15) Uani 1 1 d . . . H11 H 0.5313 -0.2912 0.8538 0.051 Uiso 1 1 calc R . . C12 C 0.5005(8) -0.2614(8) 0.9486(3) 0.0497(16) Uani 1 1 d . . . H12B H 0.5176 -0.1824 0.9884 0.060 Uiso 1 1 calc R . . H12C H 0.4458 -0.3803 0.9505 0.060 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 N1 0.023(2) 0.026(2) 0.031(2) -0.0015(18) 0.0055(18) -0.0005(19) C2 0.023(3) 0.023(3) 0.038(3) 0.005(2) 0.005(2) -0.003(2) C3 0.031(3) 0.021(3) 0.036(3) 0.004(2) -0.002(2) -0.001(2) O3 0.049(2) 0.0276(19) 0.0376(19) -0.0013(17) -0.0105(17) 0.000(2) C4 0.041(3) 0.028(3) 0.040(3) -0.005(2) 0.007(3) 0.003(3) C5 0.033(3) 0.033(3) 0.037(3) -0.004(2) 0.008(2) 0.004(3) C6 0.026(3) 0.031(3) 0.031(3) 0.005(2) 0.001(2) 0.002(2) C7 0.029(3) 0.031(3) 0.039(3) -0.002(3) 0.001(2) -0.008(3) C8 0.047(4) 0.025(3) 0.038(3) -0.003(2) 0.007(3) -0.009(3) C9 0.048(3) 0.035(3) 0.028(3) -0.002(2) 0.006(3) 0.002(3) C10 0.029(3) 0.044(4) 0.055(4) 0.014(3) 0.006(3) -0.004(3) C11 0.040(3) 0.050(4) 0.038(3) -0.001(3) 0.006(3) -0.023(3) C12 0.046(4) 0.051(4) 0.054(4) 0.005(3) 0.013(3) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.486(6) . ? C2 C3 1.522(7) . ? C3 C4 1.525(7) . ? C4 C5 1.534(7) . ? C5 C6 1.496(7) . ? C6 C7 1.510(7) . ? C7 C8 1.532(7) . ? C8 C9 1.546(7) . ? C9 N1 1.463(6) . ? N1 C6 1.481(6) . ? C2 C10 1.523(7) . ? C10 C11 1.482(7) . ? C11 C12 1.289(7) . ? C3 O3 1.425(6) . ? 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 C9 N1 C6 104.7(4) . . ? C9 N1 C2 114.6(4) . . ? C6 N1 C2 110.8(4) . . ? N1 C2 C3 110.2(4) . . ? N1 C2 C10 110.6(4) . . ? C3 C2 C10 112.6(4) . . ? O3 C3 C2 109.2(4) . . ? O3 C3 C4 110.8(4) . . ? C2 C3 C4 112.1(4) . . ? C3 C4 C5 111.9(4) . . ? C6 C5 C4 109.3(4) . . ? N1 C6 C5 110.2(4) . . ? N1 C6 C7 101.8(4) . . ? C5 C6 C7 118.1(4) . . ? C6 C7 C8 103.5(4) . . ? C7 C8 C9 104.7(4) . . ? N1 C9 C8 104.8(4) . . ? C11 C10 C2 114.0(5) . . ? C12 C11 C10 126.5(6) . . ? 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 C9 N1 C2 C3 -177.2(4) . . . . ? C6 N1 C2 C3 -59.0(5) . . . . ? C9 N1 C2 C10 57.7(5) . . . . ? C6 N1 C2 C10 175.9(4) . . . . ? N1 C2 C3 O3 -70.9(5) . . . . ? C10 C2 C3 O3 53.1(5) . . . . ? N1 C2 C3 C4 52.3(5) . . . . ? C10 C2 C3 C4 176.2(4) . . . . ? O3 C3 C4 C5 72.0(5) . . . . ? C2 C3 C4 C5 -50.3(5) . . . . ? C3 C4 C5 C6 53.4(5) . . . . ? C9 N1 C6 C5 -172.0(4) . . . . ? C2 N1 C6 C5 63.9(5) . . . . ? C9 N1 C6 C7 -46.0(5) . . . . ? C2 N1 C6 C7 -170.0(4) . . . . ? C4 C5 C6 N1 -59.8(5) . . . . ? C4 C5 C6 C7 -176.1(4) . . . . ? N1 C6 C7 C8 39.3(5) . . . . ? C5 C6 C7 C8 160.1(4) . . . . ? C6 C7 C8 C9 -19.1(5) . . . . ? C6 N1 C9 C8 33.6(5) . . . . ? C2 N1 C9 C8 155.2(4) . . . . ? C7 C8 C9 N1 -8.4(5) . . . . ? N1 C2 C10 C11 -176.7(4) . . . . ? C3 C2 C10 C11 59.6(6) . . . . ? C2 C10 C11 C12 113.0(7) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 22.52 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.26 _refine_diff_density_min -0.21 _refine_diff_density_rms 0.06 #===END