# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Steven Allin' 'David M. Andrews' 'Ian Aspinall' 'Robert D. Baird' 'Mark Edgar' 'Mark Elsegood' 'Munira Essat' 'Vickie McKee' 'Catarina Horro Pita' 'Pritom Shah' _publ_contact_author_name 'Dr Steven Allin' _publ_contact_author_address ; Department of Chemistry Loughborough University Loughborough Leics LE11 3TU ; _publ_contact_author_email S.M.ALLIN@LBORO.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Applications of the Amino-Cope Rearrangement: Synthesis of tetrahydropyran, lactone and piperidine targets. ; data_4a _database_code_depnum_ccdc_archive 'CCDC 206872' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 I O2' _chemical_formula_weight 316.12 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' I I -0.4742 1.8119 '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 6.6491(4) _cell_length_b 6.8227(4) _cell_length_c 25.8973(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1174.83(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8847 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 28.93 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.787 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 2.704 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.369 _exptl_absorpt_correction_T_max 0.518 _exptl_absorpt_process_details 'SADABS, Sheldrick, G.M.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10340 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 28.93 _reflns_number_total 2793 _reflns_number_gt 2708 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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 and local programs' _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^)+(0.0141P)^2^+0.3043P] 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 SHELXL _refine_ls_extinction_coef 0.0026(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.001(16) _refine_ls_number_reflns 2793 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0158 _refine_ls_R_factor_gt 0.0150 _refine_ls_wR_factor_ref 0.0338 _refine_ls_wR_factor_gt 0.0336 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 O1 O 0.4486(2) -0.02691(19) 0.02974(5) 0.0268(3) Uani 1 1 d . . . C1 C 0.2969(3) 0.1027(3) 0.02822(7) 0.0255(4) Uani 1 1 d . . . O2 O 0.1883(2) 0.1013(2) -0.00921(5) 0.0356(4) Uani 1 1 d . . . C2 C 0.2705(2) 0.2457(4) 0.07190(6) 0.0257(3) Uani 1 1 d . . . H2A H 0.1248 0.2656 0.0778 0.031 Uiso 1 1 calc R . . H2B H 0.3283 0.3734 0.0614 0.031 Uiso 1 1 calc R . . C3 C 0.3685(3) 0.1822(3) 0.12296(7) 0.0230(4) Uani 1 1 d . . . H3 H 0.2926 0.0659 0.1361 0.028 Uiso 1 1 calc R . . C4 C 0.5815(3) 0.1157(3) 0.11090(7) 0.0242(4) Uani 1 1 d . . . H4A H 0.6566 0.2236 0.0941 0.029 Uiso 1 1 calc R . . H4B H 0.6518 0.0806 0.1433 0.029 Uiso 1 1 calc R . . C5 C 0.5743(3) -0.0600(3) 0.07538(7) 0.0249(4) Uani 1 1 d . . . H5 H 0.5183 -0.1737 0.0950 0.030 Uiso 1 1 calc R . . C6 C 0.7738(3) -0.1206(3) 0.05204(8) 0.0302(4) Uani 1 1 d . . . H6A H 0.8391 -0.0052 0.0361 0.036 Uiso 1 1 calc R . . H6B H 0.7503 -0.2191 0.0246 0.036 Uiso 1 1 calc R . . I1 I 0.968773(17) -0.24209(2) 0.109752(5) 0.03240(5) Uani 1 1 d . . . C7 C 0.3477(3) 0.3443(3) 0.16248(7) 0.0238(4) Uani 1 1 d . . . C8 C 0.4939(3) 0.4875(3) 0.17012(8) 0.0318(4) Uani 1 1 d . . . H8 H 0.6147 0.4840 0.1506 0.038 Uiso 1 1 calc R . . C9 C 0.4638(4) 0.6366(3) 0.20647(8) 0.0368(5) Uani 1 1 d . . . H9 H 0.5646 0.7334 0.2116 0.044 Uiso 1 1 calc R . . C10 C 0.2891(4) 0.6432(3) 0.23467(8) 0.0374(5) Uani 1 1 d . . . H10 H 0.2692 0.7443 0.2594 0.045 Uiso 1 1 calc R . . C11 C 0.1429(4) 0.5033(4) 0.22709(9) 0.0382(5) Uani 1 1 d . . . H11 H 0.0215 0.5083 0.2464 0.046 Uiso 1 1 calc R . . C12 C 0.1726(3) 0.3553(3) 0.19136(8) 0.0308(4) Uani 1 1 d . . . H12 H 0.0708 0.2593 0.1865 0.037 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 0.0287(7) 0.0296(7) 0.0223(6) -0.0077(5) -0.0060(6) 0.0068(6) C1 0.0271(10) 0.0274(10) 0.0220(9) -0.0011(8) -0.0014(8) 0.0014(8) O2 0.0400(9) 0.0411(9) 0.0258(7) -0.0066(6) -0.0128(6) 0.0111(7) C2 0.0266(8) 0.0274(8) 0.0232(8) -0.0041(10) -0.0022(6) 0.0056(11) C3 0.0231(9) 0.0236(8) 0.0222(9) -0.0002(6) -0.0001(7) -0.0012(6) C4 0.0255(9) 0.0253(8) 0.0217(8) -0.0017(8) -0.0034(8) 0.0022(7) C5 0.0244(10) 0.0267(9) 0.0237(9) -0.0012(7) -0.0044(7) 0.0040(7) C6 0.0287(10) 0.0327(11) 0.0292(10) -0.0037(9) -0.0019(8) 0.0061(8) I1 0.02317(6) 0.03035(7) 0.04367(7) 0.00391(7) -0.00609(4) 0.00164(6) C7 0.0291(10) 0.0248(9) 0.0175(9) 0.0002(7) -0.0016(7) 0.0036(7) C8 0.0341(11) 0.0314(9) 0.0298(10) 0.0002(8) 0.0019(9) -0.0029(9) C9 0.0418(12) 0.0279(10) 0.0407(12) -0.0053(8) -0.0081(10) -0.0027(10) C10 0.0508(14) 0.0351(12) 0.0264(11) -0.0104(9) -0.0054(10) 0.0108(10) C11 0.0388(13) 0.0494(14) 0.0264(11) -0.0075(9) 0.0064(9) 0.0058(10) C12 0.0316(11) 0.0336(11) 0.0271(10) -0.0025(8) 0.0019(8) -0.0024(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 O1 C1 1.342(2) . ? O1 C5 1.465(2) . ? C1 O2 1.209(2) . ? C1 C2 1.504(3) . ? C2 C3 1.536(2) . ? C3 C7 1.513(3) . ? C3 C4 1.520(3) . ? C4 C5 1.511(2) . ? C5 C6 1.515(3) . ? C6 I1 2.145(2) . ? C7 C12 1.386(3) . ? C7 C8 1.392(3) . ? C8 C9 1.400(3) . ? C9 C10 1.373(3) . ? C10 C11 1.377(3) . ? C11 C12 1.384(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 C1 O1 C5 123.64(14) . . ? O2 C1 O1 117.86(18) . . ? O2 C1 C2 122.57(17) . . ? O1 C1 C2 119.55(16) . . ? C1 C2 C3 114.49(17) . . ? C7 C3 C4 116.25(15) . . ? C7 C3 C2 109.69(15) . . ? C4 C3 C2 107.61(15) . . ? C5 C4 C3 109.42(15) . . ? O1 C5 C4 112.75(15) . . ? O1 C5 C6 102.69(15) . . ? C4 C5 C6 115.59(17) . . ? C5 C6 I1 110.88(13) . . ? C12 C7 C8 118.16(18) . . ? C12 C7 C3 118.77(18) . . ? C8 C7 C3 123.04(17) . . ? C7 C8 C9 120.37(19) . . ? C10 C9 C8 120.2(2) . . ? C9 C10 C11 119.9(2) . . ? C10 C11 C12 120.0(2) . . ? C11 C12 C7 121.4(2) . . ? 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 C5 O1 C1 O2 -171.34(19) . . . . ? C5 O1 C1 C2 10.0(3) . . . . ? O2 C1 C2 C3 159.41(19) . . . . ? O1 C1 C2 C3 -22.0(3) . . . . ? C1 C2 C3 C7 175.16(16) . . . . ? C1 C2 C3 C4 47.8(2) . . . . ? C7 C3 C4 C5 173.99(15) . . . . ? C2 C3 C4 C5 -62.6(2) . . . . ? C1 O1 C5 C4 -25.1(2) . . . . ? C1 O1 C5 C6 -150.16(17) . . . . ? C3 C4 C5 O1 51.6(2) . . . . ? C3 C4 C5 C6 169.27(16) . . . . ? O1 C5 C6 I1 -166.99(12) . . . . ? C4 C5 C6 I1 69.83(19) . . . . ? C4 C3 C7 C12 -152.49(18) . . . . ? C2 C3 C7 C12 85.2(2) . . . . ? C4 C3 C7 C8 29.7(3) . . . . ? C2 C3 C7 C8 -92.7(2) . . . . ? C12 C7 C8 C9 0.6(3) . . . . ? C3 C7 C8 C9 178.47(18) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C10 C11 C12 C7 -0.2(3) . . . . ? C8 C7 C12 C11 -0.4(3) . . . . ? C3 C7 C12 C11 -178.30(18) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.272 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.049 #===END data_sma32 _database_code_depnum_ccdc_archive 'CCDC 242655' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 N O' _chemical_formula_weight 307.42 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 'P 2~1~ 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 4.9818(5) _cell_length_b 9.4157(10) _cell_length_c 37.792(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1772.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4597 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 26.05 _exptl_crystal_description block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.931789 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 '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_% 0 _diffrn_reflns_number 15019 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -49 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.76 _reflns_number_total 4177 _reflns_number_gt 3284 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0528P)^2^+0.1299P] 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 -0.2(15) _refine_ls_number_reflns 4177 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.4246(4) 0.43723(18) 0.12235(4) 0.0372(4) Uani 1 1 d . . . H1 H 0.3649 0.3821 0.1028 0.045 Uiso 1 1 calc R . . C2 C 0.6155(4) 0.3820(2) 0.14512(5) 0.0462(5) Uani 1 1 d . . . H2 H 0.6872 0.2901 0.1409 0.055 Uiso 1 1 calc R . . C3 C 0.7025(4) 0.4601(2) 0.17399(5) 0.0477(5) Uani 1 1 d . . . H3 H 0.8346 0.4226 0.1895 0.057 Uiso 1 1 calc R . . C4 C 0.5955(4) 0.5921(2) 0.17981(4) 0.0448(5) Uani 1 1 d . . . H4 H 0.6524 0.6459 0.1997 0.054 Uiso 1 1 calc R . . C5 C 0.4053(4) 0.64824(18) 0.15702(4) 0.0358(4) Uani 1 1 d . . . H5 H 0.3330 0.7398 0.1615 0.043 Uiso 1 1 calc R . . C6 C 0.3189(3) 0.57210(18) 0.12761(4) 0.0292(4) Uani 1 1 d . . . C7 C 0.1276(3) 0.64010(17) 0.10164(4) 0.0280(3) Uani 1 1 d . . . H7A H -0.0046 0.6984 0.1147 0.034 Uiso 1 1 calc R . . H7B H 0.0282 0.5649 0.0888 0.034 Uiso 1 1 calc R . . C8 C 0.2760(3) 0.73444(16) 0.07470(4) 0.0249(3) Uani 1 1 d . . . H8 H 0.4071 0.7954 0.0878 0.030 Uiso 1 1 calc R . . C9 C 0.4302(3) 0.64324(17) 0.04837(4) 0.0284(3) Uani 1 1 d . . . H9A H 0.5421 0.5745 0.0616 0.034 Uiso 1 1 calc R . . H9B H 0.3003 0.5884 0.0340 0.034 Uiso 1 1 calc R . . O1 O 0.5978(2) 0.72234(12) 0.02532(3) 0.0315(3) Uani 1 1 d . . . N1 N 0.0899(3) 0.82765(13) 0.05508(3) 0.0252(3) Uani 1 1 d . . . C10 C 0.0802(3) 0.97618(16) 0.06794(4) 0.0279(3) Uani 1 1 d . . . H10 H 0.2661 1.0162 0.0676 0.034 Uiso 1 1 calc R . . C11 C -0.0958(4) 1.06255(16) 0.04257(4) 0.0329(4) Uani 1 1 d . . . H11A H -0.0203 1.0546 0.0184 0.040 Uiso 1 1 calc R . . H11B H -0.2776 1.0201 0.0421 0.040 Uiso 1 1 calc R . . C12 C -0.1207(4) 1.2173(2) 0.05182(5) 0.0455(5) Uani 1 1 d . . . H12 H -0.1742 1.2394 0.0753 0.055 Uiso 1 1 calc R . . C13 C -0.0764(4) 1.3227(2) 0.03094(6) 0.0515(5) Uani 1 1 d . . . H13A H -0.0225 1.3059 0.0072 0.062 Uiso 1 1 calc R . . H13B H -0.0976 1.4172 0.0393 0.062 Uiso 1 1 calc R . . C14 C -0.0253(3) 0.98201(16) 0.10524(4) 0.0292(4) Uani 1 1 d . . . H14 H -0.1958 0.9406 0.1097 0.035 Uiso 1 1 calc R . . C15 C 0.1024(4) 1.04074(16) 0.13226(4) 0.0292(3) Uani 1 1 d . . . H15 H 0.2734 1.0807 0.1273 0.035 Uiso 1 1 calc R . . C16 C 0.0084(3) 1.05093(17) 0.16921(4) 0.0314(4) Uani 1 1 d . . . C17 C -0.2001(4) 0.9688(2) 0.18200(5) 0.0468(5) Uani 1 1 d . . . H17 H -0.2862 0.9027 0.1668 0.056 Uiso 1 1 calc R . . C18 C -0.2855(5) 0.9818(3) 0.21702(5) 0.0625(6) Uani 1 1 d . . . H18 H -0.4309 0.9257 0.2254 0.075 Uiso 1 1 calc R . . C19 C -0.1600(5) 1.0754(3) 0.23947(5) 0.0614(7) Uani 1 1 d . . . H19 H -0.2153 1.0828 0.2635 0.074 Uiso 1 1 calc R . . C20 C 0.0441(6) 1.1574(3) 0.22709(5) 0.0631(7) Uani 1 1 d . . . H20 H 0.1286 1.2237 0.2424 0.076 Uiso 1 1 calc R . . C21 C 0.1305(5) 1.1450(2) 0.19223(4) 0.0479(5) Uani 1 1 d . . . H21 H 0.2753 1.2020 0.1841 0.057 Uiso 1 1 calc R . . H1N H 0.1328 0.8289 0.0314 0.040 Uiso 1 1 d . . . H1O H 0.7373 0.7603 0.0378 0.040 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 0.0431(10) 0.0374(9) 0.0310(8) 0.0051(7) 0.0017(8) -0.0016(8) C2 0.0504(11) 0.0426(10) 0.0457(11) 0.0126(8) 0.0032(9) 0.0071(9) C3 0.0436(11) 0.0633(13) 0.0362(10) 0.0202(10) -0.0038(8) 0.0012(10) C4 0.0457(10) 0.0627(12) 0.0261(8) 0.0017(8) -0.0056(8) -0.0028(10) C5 0.0373(9) 0.0438(9) 0.0263(8) 0.0007(7) 0.0012(8) 0.0001(8) C6 0.0261(8) 0.0407(9) 0.0207(7) 0.0048(7) 0.0048(6) -0.0033(7) C7 0.0236(8) 0.0381(8) 0.0223(7) 0.0004(6) 0.0029(6) -0.0017(7) C8 0.0201(7) 0.0350(8) 0.0197(7) -0.0006(6) -0.0009(6) -0.0030(7) C9 0.0246(8) 0.0383(8) 0.0222(7) -0.0009(6) 0.0017(6) -0.0012(7) O1 0.0215(5) 0.0538(7) 0.0192(5) 0.0009(5) 0.0017(5) -0.0051(5) N1 0.0248(6) 0.0353(7) 0.0155(6) -0.0026(5) 0.0001(5) 0.0002(6) C10 0.0281(8) 0.0351(8) 0.0206(7) -0.0020(6) 0.0006(7) -0.0035(7) C11 0.0366(8) 0.0370(9) 0.0252(8) -0.0003(7) -0.0018(7) -0.0002(8) C12 0.0596(12) 0.0468(10) 0.0302(9) -0.0060(8) -0.0039(9) 0.0088(10) C13 0.0551(12) 0.0397(10) 0.0598(12) -0.0131(9) 0.0019(11) -0.0007(10) C14 0.0279(8) 0.0346(8) 0.0252(7) -0.0007(7) 0.0027(6) 0.0015(7) C15 0.0348(8) 0.0290(8) 0.0237(7) 0.0000(6) -0.0015(7) 0.0017(7) C16 0.0413(9) 0.0311(8) 0.0219(7) 0.0013(7) -0.0014(7) 0.0110(7) C17 0.0535(12) 0.0552(12) 0.0317(9) 0.0005(9) 0.0055(9) -0.0008(10) C18 0.0635(14) 0.0866(16) 0.0373(11) 0.0155(12) 0.0163(11) 0.0105(13) C19 0.0818(17) 0.0800(15) 0.0224(9) 0.0005(10) 0.0058(10) 0.0361(14) C20 0.0967(19) 0.0667(14) 0.0259(9) -0.0097(9) -0.0110(11) 0.0143(15) C21 0.0645(13) 0.0516(11) 0.0276(9) -0.0034(8) -0.0060(9) -0.0023(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.384(2) . ? C1 C6 1.389(2) . ? C2 C3 1.385(3) . ? C3 C4 1.371(3) . ? C4 C5 1.385(3) . ? C5 C6 1.391(2) . ? C6 C7 1.510(2) . ? C7 C8 1.540(2) . ? C8 N1 1.4762(19) . ? C8 C9 1.522(2) . ? C9 O1 1.4179(17) . ? N1 C10 1.4812(19) . ? C10 C14 1.506(2) . ? C10 C11 1.533(2) . ? C11 C12 1.503(2) . ? C12 C13 1.287(3) . ? C14 C15 1.324(2) . ? C15 C16 1.476(2) . ? C16 C21 1.382(2) . ? C16 C17 1.382(2) . ? C17 C18 1.396(3) . ? C18 C19 1.374(3) . ? C19 C20 1.359(3) . ? C20 C21 1.391(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.97(16) . . ? C1 C2 C3 120.39(17) . . ? C4 C3 C2 119.06(18) . . ? C3 C4 C5 120.82(17) . . ? C4 C5 C6 120.80(17) . . ? C1 C6 C5 117.93(15) . . ? C1 C6 C7 122.25(14) . . ? C5 C6 C7 119.74(15) . . ? C6 C7 C8 111.80(12) . . ? N1 C8 C9 108.90(11) . . ? N1 C8 C7 111.93(12) . . ? C9 C8 C7 110.42(12) . . ? O1 C9 C8 113.73(12) . . ? C8 N1 C10 114.65(11) . . ? N1 C10 C14 110.67(12) . . ? N1 C10 C11 108.33(12) . . ? C14 C10 C11 111.51(13) . . ? C12 C11 C10 114.58(13) . . ? C13 C12 C11 126.19(17) . . ? C15 C14 C10 124.72(15) . . ? C14 C15 C16 127.19(16) . . ? C21 C16 C17 117.98(16) . . ? C21 C16 C15 119.83(16) . . ? C17 C16 C15 122.19(15) . . ? C16 C17 C18 120.8(2) . . ? C19 C18 C17 120.2(2) . . ? C20 C19 C18 119.47(18) . . ? C19 C20 C21 120.7(2) . . ? C16 C21 C20 120.9(2) . . ? 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 0.8(3) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C2 C1 C6 C5 -1.8(2) . . . . ? C2 C1 C6 C7 174.87(16) . . . . ? C4 C5 C6 C1 1.5(2) . . . . ? C4 C5 C6 C7 -175.26(16) . . . . ? C1 C6 C7 C8 -93.84(18) . . . . ? C5 C6 C7 C8 82.74(17) . . . . ? C6 C7 C8 N1 -166.04(12) . . . . ? C6 C7 C8 C9 72.46(16) . . . . ? N1 C8 C9 O1 63.86(16) . . . . ? C7 C8 C9 O1 -172.86(12) . . . . ? C9 C8 N1 C10 -136.94(12) . . . . ? C7 C8 N1 C10 100.69(15) . . . . ? C8 N1 C10 C14 -63.72(16) . . . . ? C8 N1 C10 C11 173.75(12) . . . . ? N1 C10 C11 C12 -178.87(15) . . . . ? C14 C10 C11 C12 59.11(19) . . . . ? C10 C11 C12 C13 127.7(2) . . . . ? N1 C10 C14 C15 124.04(16) . . . . ? C11 C10 C14 C15 -115.30(17) . . . . ? C10 C14 C15 C16 179.36(15) . . . . ? C14 C15 C16 C21 -163.76(17) . . . . ? C14 C15 C16 C17 16.3(3) . . . . ? C21 C16 C17 C18 0.6(3) . . . . ? C15 C16 C17 C18 -179.49(18) . . . . ? C16 C17 C18 C19 -1.0(3) . . . . ? C17 C18 C19 C20 1.4(3) . . . . ? C18 C19 C20 C21 -1.4(3) . . . . ? C17 C16 C21 C20 -0.6(3) . . . . ? C15 C16 C21 C20 179.48(18) . . . . ? C19 C20 C21 C16 1.0(3) . . . . ? 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 O1 H1O N1 0.91 1.98 2.8741(16) 166.4 1_655 N1 H1N O1 0.92 2.20 3.0750(15) 157.6 4_465 _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.229 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.033