Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Shinji Yamada' 'Akie Homma' _publ_contact_author_name 'Dr Shinji Yamada' _publ_contact_author_address ; Department of Chemistry Ochanomizu University Faculty of Science 2-1-1 Otsuka Bunkyo-ku Tokyo 112-8610 JAPAN ; _publ_contact_author_email 'YAMADA@CC.OCHA.AC.JP' _publ_requested_journal 'Chemical Communications' _publ_section_title ; N-Substituent effect on the cis-trans geometry of nine-membered lactams ; data_shelxl_1a _database_code_CSD 190921 _audit_creation_method SHELXL _chemical_name_systematic ; 1-Acetylazonan-2-one ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H17 N O2' _chemical_formula_weight 183.25 _chemical_melting_point ? _chemical_compound_source ? 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 monoclinic _symmetry_space_group_name_H-M P21/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 11.988(2) _cell_length_b 7.2178(14) _cell_length_c 11.4456(15) _cell_angle_alpha 90.00 _cell_angle_beta 99.370(12) _cell_angle_gamma 90.00 _cell_volume 977.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method ? _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.692 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 230(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku afc7r' _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1870 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0109 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.95 _diffrn_reflns_theta_max 67.98 _reflns_number_total 1781 _reflns_number_observed 1680 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Rigaku afc7r' _computing_cell_refinement 'Rigaku afc7r' _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0565P)^2^+0.0000P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0660(63) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1781 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_obs 0.0409 _refine_ls_wR_factor_all 0.1681 _refine_ls_wR_factor_obs 0.1665 _refine_ls_goodness_of_fit_all 2.581 _refine_ls_goodness_of_fit_obs 2.637 _refine_ls_restrained_S_all 2.581 _refine_ls_restrained_S_obs 2.637 _refine_ls_shift/esd_max -0.059 _refine_ls_shift/esd_mean 0.010 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.67431(8) 0.49523(13) 0.76142(10) 0.0451(4) Uani 1 d . . O2 O 0.44261(9) 0.1995(2) 0.89313(10) 0.0501(4) Uani 1 d . . N1 N 0.50780(8) 0.47144(14) 0.83291(9) 0.0283(4) Uani 1 d . . C1 C 0.59431(9) 0.5728(2) 0.79207(10) 0.0308(4) Uani 1 d . . C2 C 0.58630(10) 0.7819(2) 0.79083(11) 0.0338(4) Uani 1 d . . C3 C 0.54842(11) 0.8718(2) 0.66880(11) 0.0373(4) Uani 1 d . . C4 C 0.42095(12) 0.8910(2) 0.62678(12) 0.0392(4) Uani 1 d . . C5 C 0.36591(12) 0.7396(2) 0.54317(11) 0.0412(4) Uani 1 d . . C6 C 0.38277(11) 0.5387(2) 0.58333(11) 0.0356(4) Uani 1 d . . C7 C 0.32799(10) 0.4813(2) 0.68919(12) 0.0366(4) Uani 1 d . . C8 C 0.39053(10) 0.5397(2) 0.81014(11) 0.0320(4) Uani 1 d . . C9 C 0.52396(10) 0.2918(2) 0.87928(10) 0.0328(4) Uani 1 d . . C10 C 0.64182(11) 0.2217(2) 0.91816(12) 0.0382(4) Uani 1 d . . H1 H 0.5400 0.8290 0.8496 0.057 Uiso 1 d . . H2 H 0.6600 0.8248 0.8203 0.057 Uiso 1 d . . H3 H 0.5800 0.9956 0.6764 0.057 Uiso 1 d . . H4 H 0.5800 0.8000 0.6055 0.057 Uiso 1 d . . H5 H 0.3800 0.9071 0.6987 0.057 Uiso 1 d . . H6 H 0.4000 1.0106 0.5819 0.057 Uiso 1 d . . H7 H 0.2800 0.7695 0.5207 0.057 Uiso 1 d . . H8 H 0.4000 0.7501 0.4586 0.057 Uiso 1 d . . H9 H 0.3400 0.4641 0.5150 0.057 Uiso 1 d . . H10 H 0.4600 0.5023 0.5994 0.057 Uiso 1 d . . H11 H 0.2600 0.5290 0.6817 0.057 Uiso 1 d . . H12 H 0.3200 0.3418 0.6930 0.057 Uiso 1 d . . H13 H 0.4000 0.6757 0.8200 0.057 Uiso 1 d . . H14 H 0.3600 0.4883 0.8742 0.057 Uiso 1 d . . H15 H 0.6800 0.1736 0.8475 0.057 Uiso 1 d . . H16 H 0.7000 0.3193 0.9508 0.057 Uiso 1 d . . H17 H 0.6400 0.1194 0.9716 0.057 Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0304(6) 0.0468(7) 0.0624(7) 0.0077(5) 0.0204(5) 0.0066(4) O2 0.0399(6) 0.0447(6) 0.0656(7) 0.0155(5) 0.0087(5) -0.0069(4) N1 0.0226(6) 0.0325(6) 0.0301(6) 0.0021(4) 0.0055(4) 0.0015(4) C1 0.0243(6) 0.0358(7) 0.0321(7) 0.0015(4) 0.0041(5) -0.0009(5) C2 0.0315(7) 0.0334(7) 0.0359(7) 0.0007(5) 0.0033(5) -0.0061(5) C3 0.0383(8) 0.0365(7) 0.0375(7) 0.0045(5) 0.0078(6) -0.0032(5) C4 0.0408(8) 0.0411(7) 0.0365(7) 0.0068(5) 0.0083(5) 0.0083(6) C5 0.0351(8) 0.0564(9) 0.0307(7) 0.0054(6) 0.0011(5) 0.0018(6) C6 0.0264(7) 0.0497(8) 0.0309(7) -0.0081(5) 0.0049(5) -0.0037(5) C7 0.0201(7) 0.0493(8) 0.0405(8) 0.0013(5) 0.0054(5) -0.0025(5) C8 0.0239(7) 0.0407(7) 0.0340(7) 0.0014(5) 0.0123(5) 0.0031(5) C9 0.0337(7) 0.0327(7) 0.0314(7) 0.0001(5) 0.0037(5) -0.0010(5) C10 0.0375(8) 0.0359(7) 0.0388(8) 0.0006(5) -0.0008(6) 0.0047(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 O1 C1 1.2108(15) . ? O2 C9 1.212(2) . ? N1 C9 1.403(2) . ? N1 C1 1.4096(15) . ? N1 C8 1.4723(15) . ? C1 C2 1.512(2) . ? C2 C3 1.540(2) . ? C3 C4 1.532(2) . ? C4 C5 1.529(2) . ? C5 C6 1.525(2) . ? C6 C7 1.526(2) . ? C7 C8 1.522(2) . ? C9 C10 1.499(2) . ? 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 C1 122.80(10) . . ? C9 N1 C8 116.43(10) . . ? C1 N1 C8 120.04(10) . . ? O1 C1 N1 121.08(12) . . ? O1 C1 C2 120.72(11) . . ? N1 C1 C2 118.17(10) . . ? C1 C2 C3 115.98(10) . . ? C4 C3 C2 117.05(11) . . ? C5 C4 C3 116.00(11) . . ? C6 C5 C4 117.93(10) . . ? C5 C6 C7 116.37(11) . . ? C8 C7 C6 115.79(10) . . ? N1 C8 C7 112.53(10) . . ? O2 C9 N1 119.53(11) . . ? O2 C9 C10 121.01(12) . . ? N1 C9 C10 119.34(11) . . ? 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 C1 O1 22.6(2) . . . . ? C8 N1 C1 O1 -147.25(13) . . . . ? C9 N1 C1 C2 -155.67(11) . . . . ? C8 N1 C1 C2 34.5(2) . . . . ? O1 C1 C2 C3 78.0(2) . . . . ? N1 C1 C2 C3 -103.76(12) . . . . ? C1 C2 C3 C4 86.62(14) . . . . ? C2 C3 C4 C5 -97.21(13) . . . . ? C3 C4 C5 C6 54.4(2) . . . . ? C4 C5 C6 C7 66.67(15) . . . . ? C5 C6 C7 C8 -78.51(14) . . . . ? C9 N1 C8 C7 -85.50(13) . . . . ? C1 N1 C8 C7 84.98(13) . . . . ? C6 C7 C8 N1 -56.6(2) . . . . ? C1 N1 C9 O2 -166.87(12) . . . . ? C8 N1 C9 O2 3.3(2) . . . . ? C1 N1 C9 C10 17.0(2) . . . . ? C8 N1 C9 C10 -172.76(11) . . . . ? _refine_diff_density_max 0.229 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.042 data_shelxl_1b _database_code_CSD 190922 _audit_creation_method SHELXL _chemical_name_systematic ; 1-Isobutyrylazonan-2-one ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H21 N O2' _chemical_formula_weight 211.30 _chemical_melting_point ? _chemical_compound_source ? 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 monoclinic _symmetry_space_group_name_H-M P21/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 10.068(4) _cell_length_b 23.305(2) _cell_length_c 5.1428(13) _cell_angle_alpha 90.00 _cell_angle_beta 91.86(3) _cell_angle_gamma 90.00 _cell_volume 1206.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method ? _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.621 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 230(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku afc7r' _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6101 _diffrn_reflns_av_R_equivalents 0.0741 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 67.98 _reflns_number_total 2190 _reflns_number_observed 1975 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Rigaku afc7r' _computing_cell_refinement 'Rigaku afc7r' _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0641P)^2^+0.0000P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0087(20) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2190 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_obs 0.0460 _refine_ls_wR_factor_all 0.1776 _refine_ls_wR_factor_obs 0.1740 _refine_ls_goodness_of_fit_all 2.004 _refine_ls_goodness_of_fit_obs 2.074 _refine_ls_restrained_S_all 2.004 _refine_ls_restrained_S_obs 2.074 _refine_ls_shift/esd_max 0.086 _refine_ls_shift/esd_mean 0.011 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.01262(9) 0.93032(4) 0.0621(2) 0.0368(3) Uani 1 d . . O2 O 0.28542(12) 0.82500(5) -0.2269(3) 0.0568(4) Uani 1 d . . N1 N 0.09413(11) 0.87506(4) -0.2649(2) 0.0300(3) Uani 1 d . . C1 C 0.00152(12) 0.91337(5) -0.1603(2) 0.0288(4) Uani 1 d . . C2 C -0.11033(14) 0.93506(6) -0.3359(3) 0.0357(4) Uani 1 d . . C3 C -0.24766(14) 0.90858(8) -0.2918(3) 0.0461(4) Uani 1 d . . C4 C -0.2796(2) 0.85098(9) -0.4242(3) 0.0531(5) Uani 1 d . . C5 C -0.2547(2) 0.79725(9) -0.2591(4) 0.0550(5) Uani 1 d . . C6 C -0.1151(2) 0.78655(7) -0.1475(3) 0.0444(4) Uani 1 d . . C7 C -0.0066(2) 0.77849(6) -0.3432(3) 0.0397(4) Uani 1 d . . C8 C 0.04822(14) 0.83303(6) -0.4628(2) 0.0343(4) Uani 1 d . . C9 C 0.22382(14) 0.86686(6) -0.1607(3) 0.0368(4) Uani 1 d . . C10 C 0.28908(15) 0.91331(7) 0.0051(3) 0.0432(4) Uani 1 d . . C11 C 0.3093(2) 0.96633(8) -0.1590(5) 0.0653(6) Uani 1 d . . C12 C 0.4188(2) 0.89112(9) 0.1288(4) 0.0628(5) Uani 1 d . . H1 H -0.1000 0.9329 -0.5144 0.067 Uiso 1 d . . H2 H -0.1200 0.9760 -0.2862 0.067 Uiso 1 d . . H3 H -0.3200 0.9364 -0.3511 0.067 Uiso 1 d . . H4 H -0.2600 0.9053 -0.1067 0.067 Uiso 1 d . . H5 H -0.2400 0.8484 -0.5958 0.067 Uiso 1 d . . H6 H -0.3800 0.8517 -0.4799 0.067 Uiso 1 d . . H7 H -0.2800 0.7641 -0.3670 0.067 Uiso 1 d . . H8 H -0.3200 0.7990 -0.1187 0.067 Uiso 1 d . . H9 H -0.1200 0.7511 -0.0325 0.067 Uiso 1 d . . H10 H -0.1000 0.8174 -0.0255 0.067 Uiso 1 d . . H11 H -0.0400 0.7543 -0.4869 0.067 Uiso 1 d . . H12 H 0.0600 0.7564 -0.2513 0.067 Uiso 1 d . . H13 H -0.0200 0.8511 -0.5722 0.067 Uiso 1 d . . H14 H 0.1200 0.8242 -0.5763 0.067 Uiso 1 d . . H15 H 0.2200 0.9229 0.1506 0.067 Uiso 1 d . . H16 H 0.3600 0.9566 -0.2812 0.067 Uiso 1 d . . H17 H 0.3600 0.9948 -0.0671 0.067 Uiso 1 d . . H18 H 0.2200 0.9851 -0.2157 0.067 Uiso 1 d . . H19 H 0.4600 0.9212 0.2430 0.067 Uiso 1 d . . H20 H 0.4000 0.8563 0.2492 0.067 Uiso 1 d . . H21 H 0.4800 0.8832 -0.0105 0.067 Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0401(6) 0.0402(6) 0.0303(5) -0.0033(4) 0.0042(4) 0.0004(4) O2 0.0456(7) 0.0435(7) 0.0805(9) -0.0177(6) -0.0088(6) 0.0147(5) N1 0.0319(6) 0.0268(6) 0.0311(6) -0.0023(4) 0.0002(4) 0.0019(4) C1 0.0321(7) 0.0243(6) 0.0302(6) 0.0039(4) 0.0047(5) -0.0006(5) C2 0.0388(8) 0.0352(8) 0.0330(7) 0.0032(5) 0.0017(5) 0.0089(6) C3 0.0342(8) 0.0551(10) 0.0486(9) -0.0005(7) -0.0023(6) 0.0079(7) C4 0.0383(8) 0.0684(12) 0.0519(9) -0.0077(8) -0.0113(7) -0.0028(8) C5 0.0459(9) 0.0562(11) 0.0629(10) -0.0074(8) 0.0033(7) -0.0184(8) C6 0.0575(9) 0.0375(8) 0.0379(8) 0.0031(6) -0.0018(7) -0.0137(7) C7 0.0492(8) 0.0278(8) 0.0414(8) -0.0015(5) -0.0089(6) -0.0031(6) C8 0.0415(7) 0.0314(8) 0.0299(7) -0.0042(5) -0.0003(5) 0.0017(6) C9 0.0329(7) 0.0332(8) 0.0442(8) -0.0002(6) -0.0003(6) 0.0033(6) C10 0.0343(7) 0.0407(8) 0.0543(9) -0.0078(7) -0.0031(6) -0.0017(6) C11 0.0697(12) 0.0421(11) 0.0836(13) 0.0021(9) -0.0040(10) -0.0122(9) C12 0.0429(9) 0.0641(12) 0.0801(13) -0.0001(10) -0.0180(9) -0.0037(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 1.212(2) . ? O2 C9 1.211(2) . ? N1 C9 1.408(2) . ? N1 C1 1.410(2) . ? N1 C8 1.476(2) . ? C1 C2 1.507(2) . ? C2 C3 1.538(2) . ? C3 C4 1.535(3) . ? C4 C5 1.529(3) . ? C5 C6 1.521(3) . ? C6 C7 1.521(2) . ? C7 C8 1.523(2) . ? C9 C10 1.515(2) . ? C10 C11 1.514(3) . ? C10 C12 1.525(2) . ? 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 C1 123.86(11) . . ? C9 N1 C8 115.98(11) . . ? C1 N1 C8 119.16(11) . . ? O1 C1 N1 121.63(12) . . ? O1 C1 C2 120.03(12) . . ? N1 C1 C2 118.29(11) . . ? C1 C2 C3 115.78(12) . . ? C4 C3 C2 117.54(13) . . ? C5 C4 C3 116.22(14) . . ? C6 C5 C4 118.45(14) . . ? C7 C6 C5 116.43(13) . . ? C6 C7 C8 116.20(12) . . ? N1 C8 C7 112.64(10) . . ? O2 C9 N1 118.64(13) . . ? O2 C9 C10 121.17(14) . . ? N1 C9 C10 119.81(12) . . ? C11 C10 C9 109.45(14) . . ? C11 C10 C12 112.38(15) . . ? C9 C10 C12 110.03(14) . . ? 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 C1 O1 -20.3(2) . . . . ? C8 N1 C1 O1 147.76(12) . . . . ? C9 N1 C1 C2 157.30(12) . . . . ? C8 N1 C1 C2 -34.6(2) . . . . ? O1 C1 C2 C3 -77.4(2) . . . . ? N1 C1 C2 C3 104.97(14) . . . . ? C1 C2 C3 C4 -83.8(2) . . . . ? C2 C3 C4 C5 95.4(2) . . . . ? C3 C4 C5 C6 -58.5(2) . . . . ? C4 C5 C6 C7 -62.0(2) . . . . ? C5 C6 C7 C8 79.8(2) . . . . ? C9 N1 C8 C7 83.7(2) . . . . ? C1 N1 C8 C7 -85.32(14) . . . . ? C6 C7 C8 N1 53.5(2) . . . . ? C1 N1 C9 O2 164.27(14) . . . . ? C8 N1 C9 O2 -4.2(2) . . . . ? C1 N1 C9 C10 -22.8(2) . . . . ? C8 N1 C9 C10 168.80(12) . . . . ? O2 C9 C10 C11 108.0(2) . . . . ? N1 C9 C10 C11 -64.8(2) . . . . ? O2 C9 C10 C12 -16.0(2) . . . . ? N1 C9 C10 C12 171.26(14) . . . . ? _refine_diff_density_max 0.339 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.039 data_shelxl_1c _database_code_CSD 190923 _audit_creation_method SHELXL _chemical_name_systematic ; 1-(2,2-Dimethylpropionyl)azonan-2-one ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H23 N O2' _chemical_formula_weight 225.32 _chemical_melting_point ? _chemical_compound_source ? 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 monoclinic _symmetry_space_group_name_H-M P21/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 10.462(2) _cell_length_b 22.892(5) _cell_length_c 5.5006(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.201(14) _cell_angle_gamma 90.00 _cell_volume 1313.8(4) _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 prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.139 _exptl_crystal_density_method ? _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.598 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku afc7r' _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3322 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 67.94 _reflns_number_total 2395 _reflns_number_observed 2135 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Rigaku afc7r' _computing_cell_refinement 'Rigaku afc7r' _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 5 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.1000P)^2^+0.0000P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0121(22) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2390 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_obs 0.0435 _refine_ls_wR_factor_all 0.1849 _refine_ls_wR_factor_obs 0.1698 _refine_ls_goodness_of_fit_all 1.525 _refine_ls_goodness_of_fit_obs 1.559 _refine_ls_restrained_S_all 1.601 _refine_ls_restrained_S_obs 1.559 _refine_ls_shift/esd_max -0.062 _refine_ls_shift/esd_mean 0.009 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.02471(10) 0.92193(5) 0.0267(2) 0.0414(3) Uani 1 d . . O2 O 0.27909(10) 0.81591(5) -0.2247(2) 0.0481(4) Uani 1 d . . N1 N 0.10154(10) 0.87080(4) -0.2874(2) 0.0283(3) Uani 1 d . . C1 C 0.01348(12) 0.90823(5) -0.1874(2) 0.0304(4) Uani 1 d . . C2 C -0.09429(13) 0.93246(6) -0.3539(3) 0.0370(4) Uani 1 d . . C3 C -0.22837(14) 0.90744(7) -0.3181(3) 0.0443(4) Uani 1 d . . C4 C -0.26229(14) 0.84874(8) -0.4385(3) 0.0521(5) Uani 1 d . . C5 C -0.2399(2) 0.79474(8) -0.2793(4) 0.0576(5) Uani 1 d . . C6 C -0.1047(2) 0.78260(7) -0.1715(3) 0.0503(5) Uani 1 d . . C7 C -0.00243(15) 0.77247(6) -0.3520(3) 0.0423(4) Uani 1 d . . C8 C 0.05183(12) 0.82654(6) -0.4678(2) 0.0331(4) Uani 1 d . . C9 C 0.22829(12) 0.86238(5) -0.1900(2) 0.0306(4) Uani 1 d . . C10 C 0.30784(13) 0.91280(6) -0.0710(2) 0.0335(4) Uani 1 d . . C11 C 0.26563(15) 0.97356(6) -0.1625(3) 0.0405(4) Uani 1 d . . C12 C 0.3067(2) 0.90869(8) 0.2071(3) 0.0522(5) Uani 1 d . . C13 C 0.4460(2) 0.90299(7) -0.1360(3) 0.0460(4) Uani 1 d . . H1 H -0.0800 0.9288 -0.5314 0.065 Uiso 1 d . . H2 H -0.1000 0.9744 -0.3040 0.065 Uiso 1 d . . H3 H -0.2400 0.9054 -0.1504 0.065 Uiso 1 d . . H4 H -0.3000 0.9360 -0.3789 0.065 Uiso 1 d . . H5 H -0.2200 0.8450 -0.5984 0.065 Uiso 1 d . . H6 H -0.3400 0.8485 -0.4940 0.065 Uiso 1 d . . H7 H -0.2600 0.7640 -0.3777 0.065 Uiso 1 d . . H8 H -0.3000 0.7992 -0.1589 0.065 Uiso 1 d . . H9 H -0.1000 0.7468 -0.0583 0.065 Uiso 1 d . . H10 H -0.0800 0.8151 -0.0435 0.065 Uiso 1 d . . H11 H 0.0600 0.7496 -0.2608 0.065 Uiso 1 d . . H12 H -0.0400 0.7499 -0.4921 0.065 Uiso 1 d . . H13 H 0.1200 0.8152 -0.5614 0.065 Uiso 1 d . . H14 H -0.0200 0.8461 -0.5870 0.065 Uiso 1 d . . H15 H 0.3400 1.0020 -0.1062 0.065 Uiso 1 d . . H16 H 0.2600 0.9756 -0.3464 0.065 Uiso 1 d . . H17 H 0.1800 0.9883 -0.1072 0.065 Uiso 1 d . . H18 H 0.3600 0.9386 0.2812 0.065 Uiso 1 d . . H19 H 0.3400 0.8740 0.2718 0.065 Uiso 1 d . . H20 H 0.2200 0.9133 0.2625 0.065 Uiso 1 d . . H21 H 0.5000 0.9344 -0.0539 0.065 Uiso 1 d . . H22 H 0.4800 0.8658 -0.0687 0.065 Uiso 1 d . . H23 H 0.4600 0.9018 -0.2782 0.065 Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0433(6) 0.0443(6) 0.0382(6) -0.0101(4) 0.0127(4) -0.0032(4) O2 0.0399(6) 0.0329(6) 0.0701(7) -0.0079(5) -0.0052(5) 0.0077(4) N1 0.0297(6) 0.0240(6) 0.0313(6) -0.0043(4) 0.0044(4) -0.0015(4) C1 0.0323(7) 0.0239(6) 0.0365(7) -0.0015(4) 0.0118(5) -0.0041(4) C2 0.0329(7) 0.0320(7) 0.0471(8) 0.0014(5) 0.0102(6) 0.0038(5) C3 0.0308(8) 0.0440(9) 0.0593(9) -0.0020(7) 0.0110(6) 0.0033(6) C4 0.0296(7) 0.0623(11) 0.0649(10) -0.0151(8) 0.0063(7) -0.0053(7) C5 0.0493(9) 0.0447(9) 0.0822(12) -0.0162(8) 0.0277(9) -0.0180(7) C6 0.0645(11) 0.0348(8) 0.0531(9) 0.0023(6) 0.0135(8) -0.0161(7) C7 0.0450(8) 0.0266(7) 0.0551(9) -0.0060(6) 0.0012(6) -0.0039(6) C8 0.0332(7) 0.0312(7) 0.0350(7) -0.0093(5) 0.0035(5) -0.0013(5) C9 0.0322(7) 0.0276(7) 0.0322(7) 0.0013(5) 0.0039(5) 0.0006(5) C10 0.0328(7) 0.0355(8) 0.0323(7) -0.0038(5) 0.0027(5) -0.0039(5) C11 0.0446(8) 0.0293(7) 0.0482(8) -0.0054(5) 0.0081(6) -0.0084(6) C12 0.0558(10) 0.0684(11) 0.0318(8) -0.0025(6) -0.0007(7) -0.0089(8) C13 0.0315(8) 0.0555(9) 0.0508(9) -0.0062(7) 0.0018(6) -0.0043(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 1.216(2) . ? O2 C9 1.211(2) . ? N1 C1 1.400(2) . ? N1 C9 1.407(2) . ? N1 C8 1.485(2) . ? C1 C2 1.505(2) . ? C2 C3 1.541(2) . ? C3 C4 1.528(2) . ? C4 C5 1.523(3) . ? C5 C6 1.519(3) . ? C6 C7 1.530(2) . ? C7 C8 1.521(2) . ? C9 C10 1.541(2) . ? C10 C13 1.531(2) . ? C10 C11 1.533(2) . ? C10 C12 1.533(2) . ? 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 N1 C9 124.30(10) . . ? C1 N1 C8 118.14(10) . . ? C9 N1 C8 115.80(10) . . ? O1 C1 N1 121.23(12) . . ? O1 C1 C2 120.59(12) . . ? N1 C1 C2 118.16(11) . . ? C1 C2 C3 115.71(11) . . ? C4 C3 C2 117.14(11) . . ? C5 C4 C3 116.31(14) . . ? C6 C5 C4 118.19(13) . . ? C5 C6 C7 116.75(14) . . ? C8 C7 C6 116.65(12) . . ? N1 C8 C7 113.49(10) . . ? O2 C9 N1 118.22(11) . . ? O2 C9 C10 119.71(12) . . ? N1 C9 C10 121.60(11) . . ? C13 C10 C11 108.10(11) . . ? C13 C10 C12 107.49(12) . . ? C11 C10 C12 111.10(12) . . ? C13 C10 C9 106.30(11) . . ? C11 C10 C9 113.99(11) . . ? C12 C10 C9 109.54(12) . . ? 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 C1 O1 -23.6(2) . . . . ? C8 N1 C1 O1 140.59(12) . . . . ? C9 N1 C1 C2 154.89(11) . . . . ? C8 N1 C1 C2 -40.9(2) . . . . ? O1 C1 C2 C3 -73.2(2) . . . . ? N1 C1 C2 C3 108.29(13) . . . . ? C1 C2 C3 C4 -81.5(2) . . . . ? C2 C3 C4 C5 95.0(2) . . . . ? C3 C4 C5 C6 -59.8(2) . . . . ? C4 C5 C6 C7 -61.3(2) . . . . ? C5 C6 C7 C8 79.3(2) . . . . ? C1 N1 C8 C7 -80.69(14) . . . . ? C9 N1 C8 C7 84.84(13) . . . . ? C6 C7 C8 N1 53.4(2) . . . . ? C1 N1 C9 O2 151.98(13) . . . . ? C8 N1 C9 O2 -12.6(2) . . . . ? C1 N1 C9 C10 -35.9(2) . . . . ? C8 N1 C9 C10 159.59(11) . . . . ? O2 C9 C10 C13 27.7(2) . . . . ? N1 C9 C10 C13 -144.31(12) . . . . ? O2 C9 C10 C11 146.69(13) . . . . ? N1 C9 C10 C11 -25.3(2) . . . . ? O2 C9 C10 C12 -88.1(2) . . . . ? N1 C9 C10 C12 99.83(14) . . . . ? _refine_diff_density_max 0.275 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.041 data_shelxl_1d _database_code_CSD 190924 _audit_creation_method SHELXL _chemical_name_systematic ; 2-Oxoazonane-1-carboxylic acid benzyl ester ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H21 N O3' _chemical_formula_weight 275.34 _chemical_melting_point ? _chemical_compound_source ? 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2108(13) _cell_length_b 12.2287(15) _cell_length_c 7.602(2) _cell_angle_alpha 96.600(14) _cell_angle_beta 99.012(15) _cell_angle_gamma 103.634(11) _cell_volume 723.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method ? _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.701 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 230(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku afc7r' _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4655 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 67.93 _reflns_number_total 2627 _reflns_number_observed 2534 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Rigaku afc7r' _computing_cell_refinement 'Rigaku afc7r' _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 10 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0584P)^2^+0.0000P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0135(43) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2617 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_obs 0.0432 _refine_ls_wR_factor_all 0.2064 _refine_ls_wR_factor_obs 0.1907 _refine_ls_goodness_of_fit_all 2.864 _refine_ls_goodness_of_fit_obs 2.896 _refine_ls_restrained_S_all 3.090 _refine_ls_restrained_S_obs 2.896 _refine_ls_shift/esd_max 0.041 _refine_ls_shift/esd_mean 0.010 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.32200(14) 0.92029(9) 0.69016(14) 0.0424(4) Uani 1 d . . O2 O 0.79186(12) 0.93118(9) 0.64720(12) 0.0374(3) Uani 1 d . . O3 O 0.70063(11) 0.82848(8) 0.36849(12) 0.0325(3) Uani 1 d . . N1 N 0.50543(13) 0.86344(9) 0.52737(13) 0.0279(3) Uani 1 d . . C1 C 0.4488(2) 0.88594(11) 0.6915(2) 0.0316(4) Uani 1 d . . C2 C 0.5340(2) 0.84892(14) 0.8566(2) 0.0397(4) Uani 1 d . . C3 C 0.4437(2) 0.72432(14) 0.8625(2) 0.0408(4) Uani 1 d . . C4 C 0.4594(2) 0.63530(14) 0.7077(2) 0.0422(4) Uani 1 d . . C5 C 0.2918(2) 0.57508(13) 0.5770(2) 0.0451(4) Uani 1 d . . C6 C 0.2053(2) 0.64795(12) 0.4631(2) 0.0376(4) Uani 1 d . . C7 C 0.3020(2) 0.69839(12) 0.3201(2) 0.0344(4) Uani 1 d . . C8 C 0.3758(2) 0.82674(11) 0.3593(2) 0.0302(4) Uani 1 d . . C9 C 0.6774(2) 0.87839(10) 0.5247(2) 0.0282(4) Uani 1 d . . C10 C 0.8776(2) 0.85742(13) 0.3440(2) 0.0397(4) Uani 1 d . . C11 C 0.8901(2) 0.78455(11) 0.1769(2) 0.0306(4) Uani 1 d . . C12 C 0.8199(2) 0.66743(13) 0.1467(2) 0.0397(4) Uani 1 d . . C13 C 0.8407(2) 0.60173(15) -0.0053(3) 0.0547(5) Uani 1 d . . C14 C 0.9284(2) 0.6529(2) -0.1288(2) 0.0578(6) Uani 1 d . . C15 C 0.9962(2) 0.7684(2) -0.0998(2) 0.0499(5) Uani 1 d . . C16 C 0.9780(2) 0.83433(13) 0.0522(2) 0.0382(4) Uani 1 d . . H1 H 0.5203 0.9000 0.9596 0.058 Uiso 1 d . . H2 H 0.6449 0.8400 0.8495 0.058 Uiso 1 d . . H3 H 0.3272 0.7200 0.8627 0.058 Uiso 1 d . . H4 H 0.4889 0.7000 0.9717 0.058 Uiso 1 d . . H5 H 0.5017 0.5800 0.7661 0.058 Uiso 1 d . . H6 H 0.5448 0.6800 0.6385 0.058 Uiso 1 d . . H7 H 0.2177 0.5400 0.6513 0.058 Uiso 1 d . . H8 H 0.3159 0.5200 0.4975 0.058 Uiso 1 d . . H9 H 0.1822 0.7000 0.5390 0.058 Uiso 1 d . . H10 H 0.0906 0.6000 0.3966 0.058 Uiso 1 d . . H11 H 0.2329 0.6800 0.2084 0.058 Uiso 1 d . . H12 H 0.3947 0.6600 0.3081 0.058 Uiso 1 d . . H13 H 0.2913 0.8600 0.3751 0.058 Uiso 1 d . . H14 H 0.4301 0.8600 0.2601 0.058 Uiso 1 d . . H15 H 0.9198 0.9400 0.3339 0.058 Uiso 1 d . . H16 H 0.9405 0.8400 0.4490 0.058 Uiso 1 d . . H17 H 0.7515 0.6400 0.2308 0.058 Uiso 1 d . . H18 H 0.7933 0.5200 -0.0247 0.058 Uiso 1 d . . H19 H 0.9390 0.6000 -0.2354 0.058 Uiso 1 d . . H20 H 1.0573 0.8000 -0.1905 0.058 Uiso 1 d . . H21 H 1.0250 0.9200 0.0642 0.058 Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0462(7) 0.0426(6) 0.0479(6) 0.0094(5) 0.0239(5) 0.0188(5) O2 0.0291(6) 0.0426(6) 0.0348(5) 0.0004(4) 0.0063(4) 0.0008(4) O3 0.0237(6) 0.0357(6) 0.0357(6) -0.0013(4) 0.0126(4) 0.0020(4) N1 0.0253(6) 0.0283(6) 0.0299(6) 0.0040(4) 0.0101(4) 0.0037(4) C1 0.0327(7) 0.0270(7) 0.0350(7) 0.0028(5) 0.0145(5) 0.0036(5) C2 0.0386(8) 0.0510(9) 0.0280(7) 0.0036(6) 0.0108(5) 0.0071(6) C3 0.0364(8) 0.0545(9) 0.0375(8) 0.0188(6) 0.0122(6) 0.0147(7) C4 0.0401(8) 0.0424(8) 0.0502(9) 0.0168(6) 0.0090(6) 0.0177(6) C5 0.0444(9) 0.0331(7) 0.0579(9) 0.0152(7) 0.0095(7) 0.0067(6) C6 0.0291(7) 0.0323(7) 0.0487(8) 0.0097(6) 0.0052(6) 0.0027(6) C7 0.0291(7) 0.0372(8) 0.0336(7) 0.0007(5) 0.0031(5) 0.0064(6) C8 0.0272(7) 0.0355(7) 0.0294(6) 0.0073(5) 0.0073(5) 0.0087(5) C9 0.0260(7) 0.0249(6) 0.0319(6) 0.0032(5) 0.0075(5) 0.0024(5) C10 0.0222(7) 0.0472(8) 0.0447(8) -0.0036(6) 0.0128(5) 0.0003(6) C11 0.0211(6) 0.0353(7) 0.0359(7) 0.0046(5) 0.0065(5) 0.0081(5) C12 0.0333(8) 0.0367(8) 0.0496(8) 0.0087(6) 0.0091(6) 0.0081(6) C13 0.0408(9) 0.0410(9) 0.0751(11) -0.0136(8) 0.0021(8) 0.0135(7) C14 0.0406(9) 0.0841(14) 0.0451(9) -0.0187(8) 0.0045(7) 0.0253(9) C15 0.0382(9) 0.0798(12) 0.0397(8) 0.0140(8) 0.0146(6) 0.0236(8) C16 0.0302(7) 0.0449(8) 0.0447(8) 0.0132(6) 0.0117(5) 0.0141(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 1.210(2) . ? O2 C9 1.212(2) . ? O3 C9 1.333(2) . ? O3 C10 1.4591(14) . ? N1 C9 1.384(2) . ? N1 C1 1.418(2) . ? N1 C8 1.478(2) . ? C1 C2 1.508(2) . ? C2 C3 1.538(2) . ? C3 C4 1.551(2) . ? C4 C5 1.533(2) . ? C5 C6 1.527(2) . ? C6 C7 1.545(2) . ? C7 C8 1.519(2) . ? C10 C11 1.497(2) . ? C11 C12 1.389(2) . ? C11 C16 1.389(2) . ? C12 C13 1.387(2) . ? C13 C14 1.387(3) . ? C14 C15 1.368(3) . ? C15 C16 1.380(2) . ? 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 O3 C10 113.85(9) . . ? C9 N1 C1 120.84(11) . . ? C9 N1 C8 121.15(9) . . ? C1 N1 C8 117.99(10) . . ? O1 C1 N1 119.44(12) . . ? O1 C1 C2 121.95(12) . . ? N1 C1 C2 117.94(11) . . ? C1 C2 C3 109.19(12) . . ? C2 C3 C4 115.54(11) . . ? C5 C4 C3 114.99(12) . . ? C6 C5 C4 117.45(12) . . ? C5 C6 C7 115.71(12) . . ? C8 C7 C6 114.83(11) . . ? N1 C8 C7 112.41(10) . . ? O2 C9 O3 124.42(11) . . ? O2 C9 N1 124.48(11) . . ? O3 C9 N1 111.10(10) . . ? O3 C10 C11 108.45(10) . . ? C12 C11 C16 119.27(13) . . ? C12 C11 C10 121.22(12) . . ? C16 C11 C10 119.48(12) . . ? C13 C12 C11 119.73(14) . . ? C12 C13 C14 120.2(2) . . ? C15 C14 C13 120.00(14) . . ? C14 C15 C16 120.2(2) . . ? C15 C16 C11 120.53(14) . . ? 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 C1 O1 148.33(13) . . . . ? C8 N1 C1 O1 -30.0(2) . . . . ? C9 N1 C1 C2 -40.9(2) . . . . ? C8 N1 C1 C2 140.78(12) . . . . ? O1 C1 C2 C3 84.0(2) . . . . ? N1 C1 C2 C3 -86.58(14) . . . . ? C1 C2 C3 C4 65.30(15) . . . . ? C2 C3 C4 C5 -113.52(14) . . . . ? C3 C4 C5 C6 64.7(2) . . . . ? C4 C5 C6 C7 67.2(2) . . . . ? C5 C6 C7 C8 -110.50(14) . . . . ? C9 N1 C8 C7 93.71(13) . . . . ? C1 N1 C8 C7 -87.95(13) . . . . ? C6 C7 C8 N1 62.52(13) . . . . ? C10 O3 C9 O2 -9.2(2) . . . . ? C10 O3 C9 N1 169.91(11) . . . . ? C1 N1 C9 O2 -15.3(2) . . . . ? C8 N1 C9 O2 162.94(12) . . . . ? C1 N1 C9 O3 165.56(11) . . . . ? C8 N1 C9 O3 -16.16(15) . . . . ? C9 O3 C10 C11 172.50(11) . . . . ? O3 C10 C11 C12 -48.8(2) . . . . ? O3 C10 C11 C16 133.11(12) . . . . ? C16 C11 C12 C13 1.1(2) . . . . ? C10 C11 C12 C13 -176.97(13) . . . . ? C11 C12 C13 C14 -1.3(2) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C13 C14 C15 C16 0.1(2) . . . . ? C14 C15 C16 C11 -0.3(2) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C10 C11 C16 C15 177.77(13) . . . . ? _refine_diff_density_max 0.244 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.040