# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Avinash Thadani' _publ_contact_author_email ATHADANI@UWINDSOR.CA _publ_section_title ; ; loop_ _publ_author_name 'Avinash Thadani' 'Benjamin F T Cooper' 'Bhartesh Dhudshia' 'Charles Macdonald' # Attachment 'Hydroxyalkyne_16.cif' data_p212121 _database_code_depnum_ccdc_archive 'CCDC 703221' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Title: Asymmetric Total Synthesis of Securinine Authors: Bhartesh Dhudshia, Benjamin F. T. Cooper, Charles L. B. Macdonald and Avinash N. Thadani Submitted to: Chemical Communications, Sept. 2008 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H15 N O' _chemical_formula_sum 'C10 H15 N O' _chemical_formula_weight 165.23 _chemical_absolute_configuration syn 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 Orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall P2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.4042(10) _cell_length_b 8.5718(11) _cell_length_c 14.7778(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 937.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7870 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 28.05 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.894 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; the crystal was coated in Nujol and place in the cold N2 stream of the diffractometer ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 10354 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1266 _reflns_number_gt 1211 _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 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0659P)^2^+0.1190P] 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 mixed _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 ? _refine_ls_number_reflns 1266 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.3141(2) 0.44205(16) 0.01925(9) 0.0260(3) Uani 1 1 d . . . H1A H 0.2214 0.4321 -0.0296 0.031 Uiso 1 1 calc R . . C2 C 0.4761(2) 0.53412(18) -0.01747(11) 0.0350(4) Uani 1 1 d . . . H2A H 0.4412 0.5945 -0.0718 0.042 Uiso 1 1 calc R . . H2B H 0.5759 0.4626 -0.0338 0.042 Uiso 1 1 calc R . . C3 C 0.5343(2) 0.64452(17) 0.05969(11) 0.0292(3) Uani 1 1 d . . . H3 H 0.6625 0.6244 0.0774 0.035 Uiso 1 1 calc R . . C4 C 0.4065(2) 0.60318(16) 0.13731(9) 0.0255(3) Uani 1 1 d . . . H4 H 0.4599 0.5136 0.1714 0.031 Uiso 1 1 calc R . . C5 C 0.3564(3) 0.72888(19) 0.20481(10) 0.0371(4) Uani 1 1 d . . . H5A H 0.3063 0.8205 0.1727 0.044 Uiso 1 1 calc R . . H5B H 0.4652 0.7627 0.2384 0.044 Uiso 1 1 calc R . . C6 C 0.2164(3) 0.6641(2) 0.27057(11) 0.0437(4) Uani 1 1 d . . . H6A H 0.2711 0.5791 0.3067 0.052 Uiso 1 1 calc R . . H6B H 0.1780 0.7475 0.3127 0.052 Uiso 1 1 calc R . . C7 C 0.0528(2) 0.6019(2) 0.22006(11) 0.0398(4) Uani 1 1 d . . . H7A H -0.0094 0.6889 0.1889 0.048 Uiso 1 1 calc R . . H7B H -0.0329 0.5548 0.2636 0.048 Uiso 1 1 calc R . . C8 C 0.1099(2) 0.47985(17) 0.15081(10) 0.0304(3) Uani 1 1 d . . . H8A H 0.1616 0.3881 0.1822 0.036 Uiso 1 1 calc R . . H8B H 0.0035 0.4450 0.1157 0.036 Uiso 1 1 calc R . . C9 C 0.36208(19) 0.28490(17) 0.05207(10) 0.0293(3) Uani 1 1 d . . . C10 C 0.3930(2) 0.15656(18) 0.07625(13) 0.0382(4) Uani 1 1 d . . . H10 H 0.4179 0.0532 0.0957 0.046 Uiso 1 1 calc R . . N N 0.24439(15) 0.54709(13) 0.08990(7) 0.0224(3) Uani 1 1 d . . . O O 0.50996(18) 0.80357(13) 0.03554(8) 0.0388(3) Uani 1 1 d . . . H1 H 0.591(4) 0.823(3) -0.0032(15) 0.061(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0319(7) 0.0211(6) 0.0250(6) -0.0007(5) 0.0018(6) 0.0015(6) C2 0.0440(9) 0.0246(7) 0.0365(7) -0.0007(6) 0.0169(7) -0.0010(7) C3 0.0264(7) 0.0213(6) 0.0398(8) 0.0057(6) 0.0047(6) 0.0004(5) C4 0.0298(7) 0.0211(6) 0.0257(6) 0.0032(5) -0.0014(6) 0.0002(6) C5 0.0531(10) 0.0297(7) 0.0284(7) -0.0056(6) 0.0007(7) -0.0019(8) C6 0.0630(11) 0.0439(9) 0.0243(7) -0.0028(7) 0.0094(8) 0.0073(9) C7 0.0427(9) 0.0452(9) 0.0314(7) 0.0070(7) 0.0152(7) 0.0099(8) C8 0.0301(7) 0.0305(7) 0.0306(7) 0.0079(6) 0.0059(6) -0.0015(6) C9 0.0270(7) 0.0230(7) 0.0380(7) -0.0028(6) 0.0013(6) -0.0017(6) C10 0.0309(7) 0.0219(6) 0.0617(10) 0.0049(7) 0.0024(8) 0.0009(6) N 0.0256(6) 0.0198(5) 0.0219(5) 0.0020(4) 0.0026(4) 0.0014(5) O 0.0512(7) 0.0190(5) 0.0462(6) 0.0044(5) 0.0165(6) -0.0036(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N 1.4721(16) . ? C1 C9 1.475(2) . ? C1 C2 1.535(2) . ? C1 H1A 1.0000 . ? C2 C3 1.543(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O 1.4207(17) . ? C3 C4 1.528(2) . ? C3 H3 1.0000 . ? C4 N 1.4707(18) . ? C4 C5 1.514(2) . ? C4 H4 1.0000 . ? C5 C6 1.526(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.519(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.523(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N 1.4607(17) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.179(2) . ? C10 H10 0.9500 . ? O H1 0.85(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N C1 C9 114.20(11) . . ? N C1 C2 102.14(11) . . ? C9 C1 C2 113.41(13) . . ? N C1 H1A 108.9 . . ? C9 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? C1 C2 C3 105.79(12) . . ? C1 C2 H2A 110.6 . . ? C3 C2 H2A 110.6 . . ? C1 C2 H2B 110.6 . . ? C3 C2 H2B 110.6 . . ? H2A C2 H2B 108.7 . . ? O C3 C4 109.43(12) . . ? O C3 C2 111.57(13) . . ? C4 C3 C2 103.87(11) . . ? O C3 H3 110.6 . . ? C4 C3 H3 110.6 . . ? C2 C3 H3 110.6 . . ? N C4 C5 110.27(13) . . ? N C4 C3 102.91(11) . . ? C5 C4 C3 118.74(13) . . ? N C4 H4 108.1 . . ? C5 C4 H4 108.1 . . ? C3 C4 H4 108.1 . . ? C4 C5 C6 109.08(13) . . ? C4 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? C4 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? C7 C6 C5 110.89(13) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C6 C7 C8 110.46(14) . . ? C6 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? C6 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? N C8 C7 109.40(12) . . ? N C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? N C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C10 C9 C1 176.73(16) . . ? C9 C10 H10 180.0 . . ? C8 N C4 113.06(11) . . ? C8 N C1 115.76(11) . . ? C4 N C1 104.58(11) . . ? C3 O H1 105.4(16) . . ? 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 N C1 C2 C3 24.12(15) . . . . ? C9 C1 C2 C3 -99.24(14) . . . . ? C1 C2 C3 O -115.35(14) . . . . ? C1 C2 C3 C4 2.43(15) . . . . ? O C3 C4 N 91.02(13) . . . . ? C2 C3 C4 N -28.23(14) . . . . ? O C3 C4 C5 -31.06(18) . . . . ? C2 C3 C4 C5 -150.31(14) . . . . ? N C4 C5 C6 56.95(16) . . . . ? C3 C4 C5 C6 175.26(13) . . . . ? C4 C5 C6 C7 -55.94(19) . . . . ? C5 C6 C7 C8 55.87(19) . . . . ? C6 C7 C8 N -55.92(17) . . . . ? N C1 C9 C10 106(3) . . . . ? C2 C1 C9 C10 -137(3) . . . . ? C7 C8 N C4 58.92(15) . . . . ? C7 C8 N C1 179.53(12) . . . . ? C5 C4 N C8 -60.29(15) . . . . ? C3 C4 N C8 172.08(11) . . . . ? C5 C4 N C1 172.93(11) . . . . ? C3 C4 N C1 45.29(12) . . . . ? C9 C1 N C8 -45.40(17) . . . . ? C2 C1 N C8 -168.23(12) . . . . ? C9 C1 N C4 79.69(14) . . . . ? C2 C1 N C4 -43.14(13) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.228 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.049 # Attachment 'Securinine.cif' data_p21212a1 _database_code_depnum_ccdc_archive 'CCDC 703222' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Title: Asymmetric Total Synthesis of Securinine Authors: Bhartesh Dhudshia, Benjamin F. T. Cooper, Charles L. B. Macdonald and Avinash N. Thadani Submitted to: Chemical Communications, Sept. 2008 ; _chemical_name_common securinine _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N O2' _chemical_formula_sum 'C13 H15 N O2' _chemical_formula_weight 217.26 _chemical_absolute_configuration syn 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 Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.9876(10) _cell_length_b 9.3485(13) _cell_length_c 16.411(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1072.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5852 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 28.13 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.864 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 12043 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1416 _reflns_number_gt 1284 _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 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0496P)^2^+0.2324P] 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 1416 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 0.3948(3) 0.9108(2) 0.41544(12) 0.0279(4) Uani 1 1 d . . . C2 C 0.5192(3) 0.7880(2) 0.43137(11) 0.0276(4) Uani 1 1 d . . . H2 H 0.4980 0.7164 0.4714 0.033 Uiso 1 1 calc R . . C3 C 0.6664(3) 0.7934(2) 0.38060(11) 0.0234(4) Uani 1 1 d . . . C4 C 0.8423(3) 0.7133(2) 0.36926(11) 0.0281(4) Uani 1 1 d . . . H4 H 0.8587 0.6223 0.3941 0.034 Uiso 1 1 calc R . . C5 C 0.9806(3) 0.7696(2) 0.32335(12) 0.0305(5) Uani 1 1 d . . . H5 H 1.0965 0.7182 0.3159 0.037 Uiso 1 1 calc R . . C6 C 0.9563(3) 0.9149(2) 0.28267(12) 0.0277(4) Uani 1 1 d . . . H6 H 1.0825 0.9616 0.2720 0.033 Uiso 1 1 calc R . . C7 C 0.8922(3) 0.8358(2) 0.13472(12) 0.0305(5) Uani 1 1 d . . . H7A H 0.8790 0.7311 0.1421 0.037 Uiso 1 1 calc R . . H7B H 1.0267 0.8575 0.1205 0.037 Uiso 1 1 calc R . . C8 C 0.7576(3) 0.8885(3) 0.06780(12) 0.0350(5) Uani 1 1 d . . . H8A H 0.7830 0.8345 0.0171 0.042 Uiso 1 1 calc R . . H8B H 0.7836 0.9909 0.0569 0.042 Uiso 1 1 calc R . . C9 C 0.5472(3) 0.8703(2) 0.09150(12) 0.0338(5) Uani 1 1 d . . . H9A H 0.5150 0.7672 0.0916 0.041 Uiso 1 1 calc R . . H9B H 0.4659 0.9177 0.0501 0.041 Uiso 1 1 calc R . . C10 C 0.5025(3) 0.9336(2) 0.17561(12) 0.0292(5) Uani 1 1 d . . . H10A H 0.5142 1.0391 0.1741 0.035 Uiso 1 1 calc R . . H10B H 0.3703 0.9088 0.1921 0.035 Uiso 1 1 calc R . . C11 C 0.6442(3) 0.8715(2) 0.23515(11) 0.0217(4) Uani 1 1 d . . . H11 H 0.6327 0.7649 0.2338 0.026 Uiso 1 1 calc R . . C12 C 0.6442(3) 0.9208(2) 0.32554(11) 0.0217(4) Uani 1 1 d . . . C13 C 0.8262(3) 1.0100(2) 0.33467(12) 0.0273(4) Uani 1 1 d . . . H13A H 0.8698 1.0160 0.3920 0.033 Uiso 1 1 calc R . . H13B H 0.8120 1.1073 0.3116 0.033 Uiso 1 1 calc R . . N N 0.8370(2) 0.91061(18) 0.20878(10) 0.0252(4) Uani 1 1 d . . . O1 O 0.4705(2) 0.98724(15) 0.35156(8) 0.0272(3) Uani 1 1 d . . . O2 O 0.2501(2) 0.94962(19) 0.44842(10) 0.0387(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0284(10) 0.0327(11) 0.0226(9) -0.0026(8) 0.0013(9) -0.0060(9) C2 0.0347(11) 0.0265(10) 0.0217(9) 0.0005(8) 0.0000(9) -0.0041(9) C3 0.0293(10) 0.0209(9) 0.0201(8) -0.0021(7) -0.0046(8) -0.0034(9) C4 0.0348(11) 0.0273(9) 0.0221(9) -0.0016(8) -0.0070(9) 0.0060(10) C5 0.0253(10) 0.0405(12) 0.0258(9) -0.0074(9) -0.0056(9) 0.0096(9) C6 0.0204(9) 0.0368(11) 0.0258(9) -0.0035(9) 0.0013(8) -0.0022(9) C7 0.0311(11) 0.0372(12) 0.0232(9) -0.0023(8) 0.0018(9) 0.0080(9) C8 0.0445(13) 0.0385(12) 0.0219(9) 0.0009(9) 0.0019(10) 0.0104(10) C9 0.0386(12) 0.0369(12) 0.0258(10) 0.0031(9) -0.0121(10) 0.0060(10) C10 0.0265(11) 0.0328(10) 0.0282(9) 0.0045(9) -0.0023(9) 0.0055(9) C11 0.0222(9) 0.0217(9) 0.0213(8) 0.0004(7) 0.0008(8) 0.0015(8) C12 0.0209(9) 0.0209(8) 0.0234(8) -0.0007(7) 0.0007(8) 0.0016(8) C13 0.0287(10) 0.0263(10) 0.0268(10) -0.0022(8) 0.0026(9) -0.0064(9) N 0.0229(8) 0.0308(9) 0.0220(7) -0.0007(7) 0.0015(7) 0.0022(8) O1 0.0266(7) 0.0267(7) 0.0282(7) 0.0027(6) 0.0071(6) 0.0045(6) O2 0.0315(8) 0.0489(10) 0.0355(8) 0.0010(8) 0.0113(7) 0.0044(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 C1 O2 1.203(3) . ? C1 O1 1.374(2) . ? C1 C2 1.464(3) . ? C2 C3 1.324(3) . ? C2 H2 0.9500 . ? C3 C4 1.452(3) . ? C3 C12 1.503(3) . ? C4 C5 1.334(3) . ? C4 H4 0.9500 . ? C5 C6 1.523(3) . ? C5 H5 0.9500 . ? C6 N 1.472(3) . ? C6 C13 1.531(3) . ? C6 H6 1.0000 . ? C7 N 1.454(2) . ? C7 C8 1.528(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.530(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.534(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.508(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N 1.461(3) . ? C11 C12 1.553(3) . ? C11 H11 1.0000 . ? C12 O1 1.429(2) . ? C12 C13 1.528(3) . ? C13 H13A 0.9900 . ? C13 H13B 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 O2 C1 O1 120.7(2) . . ? O2 C1 C2 130.9(2) . . ? O1 C1 C2 108.38(17) . . ? C3 C2 C1 108.60(17) . . ? C3 C2 H2 125.7 . . ? C1 C2 H2 125.7 . . ? C2 C3 C4 135.95(18) . . ? C2 C3 C12 109.17(18) . . ? C4 C3 C12 114.76(17) . . ? C5 C4 C3 118.84(19) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 121.26(18) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? N C6 C5 113.60(17) . . ? N C6 C13 97.99(16) . . ? C5 C6 C13 109.86(16) . . ? N C6 H6 111.6 . . ? C5 C6 H6 111.6 . . ? C13 C6 H6 111.6 . . ? N C7 C8 106.40(17) . . ? N C7 H7A 110.4 . . ? C8 C7 H7A 110.4 . . ? N C7 H7B 110.4 . . ? C8 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? C7 C8 C9 111.88(18) . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 112.44(19) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 107.49(16) . . ? C11 C10 H10A 110.2 . . ? C9 C10 H10A 110.2 . . ? C11 C10 H10B 110.2 . . ? C9 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? N C11 C10 108.48(15) . . ? N C11 C12 102.05(15) . . ? C10 C11 C12 120.30(16) . . ? N C11 H11 108.5 . . ? C10 C11 H11 108.5 . . ? C12 C11 H11 108.5 . . ? O1 C12 C3 104.62(16) . . ? O1 C12 C13 116.12(15) . . ? C3 C12 C13 106.72(16) . . ? O1 C12 C11 114.49(15) . . ? C3 C12 C11 109.83(15) . . ? C13 C12 C11 104.80(15) . . ? C12 C13 C6 97.03(15) . . ? C12 C13 H13A 112.4 . . ? C6 C13 H13A 112.4 . . ? C12 C13 H13B 112.4 . . ? C6 C13 H13B 112.4 . . ? H13A C13 H13B 109.9 . . ? C7 N C11 111.80(16) . . ? C7 N C6 123.47(16) . . ? C11 N C6 106.54(15) . . ? C1 O1 C12 109.20(16) . . ? 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 O2 C1 C2 C3 -177.7(2) . . . . ? O1 C1 C2 C3 1.8(2) . . . . ? C1 C2 C3 C4 174.2(2) . . . . ? C1 C2 C3 C12 -1.5(2) . . . . ? C2 C3 C4 C5 -164.2(2) . . . . ? C12 C3 C4 C5 11.3(2) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C4 C5 C6 N -78.0(2) . . . . ? C4 C5 C6 C13 30.6(3) . . . . ? N C7 C8 C9 -54.4(3) . . . . ? C7 C8 C9 C10 51.1(3) . . . . ? C8 C9 C10 C11 -52.4(2) . . . . ? C9 C10 C11 N 59.9(2) . . . . ? C9 C10 C11 C12 176.70(18) . . . . ? C2 C3 C12 O1 0.8(2) . . . . ? C4 C3 C12 O1 -175.94(15) . . . . ? C2 C3 C12 C13 124.36(17) . . . . ? C4 C3 C12 C13 -52.3(2) . . . . ? C2 C3 C12 C11 -122.57(17) . . . . ? C4 C3 C12 C11 60.7(2) . . . . ? N C11 C12 O1 139.43(15) . . . . ? C10 C11 C12 O1 19.4(2) . . . . ? N C11 C12 C3 -103.24(17) . . . . ? C10 C11 C12 C3 136.75(18) . . . . ? N C11 C12 C13 11.07(18) . . . . ? C10 C11 C12 C13 -108.94(19) . . . . ? O1 C12 C13 C6 -167.30(15) . . . . ? C3 C12 C13 C6 76.55(18) . . . . ? C11 C12 C13 C6 -39.93(18) . . . . ? N C6 C13 C12 53.56(17) . . . . ? C5 C6 C13 C12 -65.16(19) . . . . ? C8 C7 N C11 64.9(2) . . . . ? C8 C7 N C6 -165.95(18) . . . . ? C10 C11 N C7 -70.09(19) . . . . ? C12 C11 N C7 161.94(15) . . . . ? C10 C11 N C6 152.31(16) . . . . ? C12 C11 N C6 24.34(18) . . . . ? C5 C6 N C7 -65.8(2) . . . . ? C13 C6 N C7 178.34(18) . . . . ? C5 C6 N C11 65.5(2) . . . . ? C13 C6 N C11 -50.31(18) . . . . ? O2 C1 O1 C12 178.25(18) . . . . ? C2 C1 O1 C12 -1.3(2) . . . . ? C3 C12 O1 C1 0.37(19) . . . . ? C13 C12 O1 C1 -116.95(18) . . . . ? C11 C12 O1 C1 120.64(17) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.235 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.040