# 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 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Brian Connell' _publ_contact_author_email CONNELL@MAIL.CHEM.TAMU.EDU _publ_section_title ; Conversion of Nitrosobenzenes to Isoxazolidines: An Efficient Cascade Process Utilizing Reactive Nitrone Intermediates ; loop_ _publ_author_name 'Brian Connell' 'Alejandro Bugarin' 'Jun Yong Kang.' # Attachment 'ccn.cif' data_ccn _database_code_depnum_ccdc_archive 'CCDC 682983' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H23 N O' _chemical_formula_weight 329.42 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 Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.227(7) _cell_length_b 32.76(2) _cell_length_c 5.358(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.235(8) _cell_angle_gamma 90.00 _cell_volume 1782(2) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 1151 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.52 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9817 _exptl_absorpt_correction_T_max 0.9978 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 8387 _diffrn_reflns_av_R_equivalents 0.0714 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3136 _reflns_number_gt 2124 _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 'X-SEED (Barbour, 2001)' _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 [0.00000+1.00000exp(1.00(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0633P)^2^+0.0000sin\q/\l] where P = 0.33333Fo^2^ + 0.66667Fc^2^ ; _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 0.0133(16) _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 -3(2) _refine_ls_number_reflns 3136 _refine_ls_number_parameters 229 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0931 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.084 _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 C1 C 0.2185(4) 0.18952(10) 0.9957(7) 0.0343(9) Uani 1 1 d . . . H1 H 0.3060 0.1854 1.1557 0.041 Uiso 1 1 calc R . . C2 C 0.1127(4) 0.16421(11) 1.0297(7) 0.0383(9) Uani 1 1 d . . . H2A H 0.0237 0.1746 0.9100 0.046 Uiso 1 1 calc R . . H2B H 0.1247 0.1644 1.2238 0.046 Uiso 1 1 calc R . . C3 C 0.1329(3) 0.12118(11) 0.9418(7) 0.0355(9) Uani 1 1 d . . . H3 H 0.1952 0.1056 1.1061 0.043 Uiso 1 1 calc R . . C4 C 0.0070(4) 0.09757(11) 0.7994(8) 0.0376(9) Uani 1 1 d . . . C5 C -0.0843(4) 0.10982(13) 0.5373(9) 0.0495(10) Uani 1 1 d . . . H5 H -0.0637 0.1329 0.4553 0.059 Uiso 1 1 calc R . . C6 C -0.2019(5) 0.09032(15) 0.3925(10) 0.0618(12) Uani 1 1 d . . . H6 H -0.2597 0.0990 0.2119 0.074 Uiso 1 1 calc R . . C7 C -0.2337(4) 0.05838(14) 0.5127(10) 0.0578(12) Uani 1 1 d . . . H7 H -0.3160 0.0451 0.4167 0.069 Uiso 1 1 calc R . . C8 C -0.1503(4) 0.04489(12) 0.7684(10) 0.0538(12) Uani 1 1 d . . . H8 H -0.1752 0.0221 0.8456 0.065 Uiso 1 1 calc R . . C9 C -0.0261(4) 0.06420(11) 0.9231(8) 0.0467(10) Uani 1 1 d . . . C10 C 0.0615(5) 0.04825(14) 1.1940(10) 0.0635(13) Uani 1 1 d . . . H10A H 0.1436 0.0388 1.1903 0.095 Uiso 1 1 calc R . . H10B H 0.0187 0.0254 1.2412 0.095 Uiso 1 1 calc R . . H10C H 0.0811 0.0698 1.3326 0.095 Uiso 1 1 calc R . . C11 C 0.1873(3) 0.23451(11) 0.9450(7) 0.0341(9) Uani 1 1 d . . . C12 C 0.0971(4) 0.24710(11) 0.6832(8) 0.0383(9) Uani 1 1 d . . . H12 H 0.0592 0.2277 0.5391 0.046 Uiso 1 1 calc R . . C13 C 0.0630(4) 0.28788(12) 0.6335(8) 0.0416(9) Uani 1 1 d . . . H13 H 0.0023 0.2964 0.4548 0.050 Uiso 1 1 calc R . . C14 C 0.1163(4) 0.31610(12) 0.8411(8) 0.0431(10) Uani 1 1 d . . . H14 H 0.0921 0.3440 0.8068 0.052 Uiso 1 1 calc R . . C15 C 0.2056(4) 0.30367(12) 1.1007(8) 0.0426(10) Uani 1 1 d . . . H15 H 0.2427 0.3235 1.2427 0.051 Uiso 1 1 calc R . . C16 C 0.2425(4) 0.26279(11) 1.1598(7) 0.0369(9) Uani 1 1 d . . . C17 C 0.3393(4) 0.25070(12) 1.4426(7) 0.0444(10) Uani 1 1 d . . . H17A H 0.3543 0.2738 1.5691 0.067 Uiso 1 1 calc R . . H17B H 0.4226 0.2429 1.4381 0.067 Uiso 1 1 calc R . . H17C H 0.3044 0.2275 1.5063 0.067 Uiso 1 1 calc R . . C18 C 0.3055(3) 0.10544(11) 0.7775(7) 0.0334(8) Uani 1 1 d . . . C19 C 0.3129(4) 0.06458(12) 0.8566(8) 0.0440(10) Uani 1 1 d . . . H19 H 0.2489 0.0536 0.9100 0.053 Uiso 1 1 calc R . . C20 C 0.4127(4) 0.04032(12) 0.8571(8) 0.0468(10) Uani 1 1 d . . . H20 H 0.4162 0.0124 0.9076 0.056 Uiso 1 1 calc R . . C21 C 0.5090(4) 0.05603(12) 0.7847(8) 0.0465(10) Uani 1 1 d . . . H21 H 0.5793 0.0393 0.7905 0.056 Uiso 1 1 calc R . . C22 C 0.5005(4) 0.09618(12) 0.7047(8) 0.0432(10) Uani 1 1 d . . . H22 H 0.5651 0.1070 0.6526 0.052 Uiso 1 1 calc R . . C23 C 0.4000(3) 0.12118(12) 0.6982(7) 0.0378(9) Uani 1 1 d . . . H23 H 0.3952 0.1488 0.6405 0.045 Uiso 1 1 calc R . . N1 N 0.1953(3) 0.12908(9) 0.7496(6) 0.0372(8) Uani 1 1 d . . . O1 O 0.2182(2) 0.17236(7) 0.7452(4) 0.0378(6) 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 0.036(2) 0.036(2) 0.0273(19) 0.0002(16) 0.0111(16) -0.0022(16) C2 0.045(2) 0.041(2) 0.0335(19) -0.0027(17) 0.0221(18) -0.0029(17) C3 0.040(2) 0.038(2) 0.031(2) 0.0020(16) 0.0170(18) 0.0015(17) C4 0.040(2) 0.037(2) 0.043(2) -0.0004(17) 0.024(2) 0.0014(18) C5 0.039(2) 0.053(3) 0.052(3) -0.017(2) 0.015(2) -0.004(2) C6 0.054(3) 0.068(3) 0.061(3) -0.012(3) 0.022(2) 0.000(2) C7 0.049(3) 0.061(3) 0.064(3) -0.009(3) 0.025(3) 0.002(2) C8 0.059(3) 0.041(2) 0.078(3) -0.008(2) 0.046(3) -0.007(2) C9 0.056(3) 0.039(2) 0.053(3) 0.002(2) 0.030(2) 0.006(2) C10 0.073(3) 0.062(3) 0.063(3) -0.003(2) 0.036(3) -0.006(2) C11 0.030(2) 0.041(2) 0.032(2) 0.0019(17) 0.0146(18) 0.0016(17) C12 0.036(2) 0.042(2) 0.035(2) 0.0026(18) 0.0139(18) 0.0070(18) C13 0.036(2) 0.050(3) 0.034(2) 0.0069(18) 0.0104(18) 0.0098(18) C14 0.040(2) 0.044(2) 0.046(2) -0.0020(19) 0.019(2) -0.0029(17) C15 0.043(2) 0.048(2) 0.040(2) -0.0059(19) 0.0203(19) -0.0042(19) C16 0.034(2) 0.041(2) 0.038(2) -0.0025(17) 0.0188(18) -0.0073(18) C17 0.043(2) 0.055(3) 0.031(2) -0.0032(18) 0.0116(18) -0.007(2) C18 0.031(2) 0.039(2) 0.0289(19) -0.0048(16) 0.0117(16) 0.0007(16) C19 0.051(3) 0.042(2) 0.045(2) 0.0062(18) 0.026(2) 0.0011(19) C20 0.049(2) 0.038(2) 0.055(3) 0.006(2) 0.024(2) 0.012(2) C21 0.044(2) 0.047(2) 0.051(3) 0.001(2) 0.023(2) 0.008(2) C22 0.040(2) 0.047(2) 0.043(2) 0.0004(19) 0.0188(19) 0.0023(19) C23 0.039(2) 0.040(2) 0.034(2) 0.0006(17) 0.0145(17) -0.0018(17) N1 0.0421(19) 0.0359(17) 0.0379(17) 0.0035(14) 0.0214(15) -0.0008(14) O1 0.0506(17) 0.0333(14) 0.0345(13) 0.0001(11) 0.0230(13) 0.0022(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.453(4) . ? C1 C11 1.512(5) . ? C1 C2 1.522(5) . ? C1 H1 1.0000 . ? C2 C3 1.534(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N1 1.494(4) . ? C3 C4 1.503(5) . ? C3 H3 1.0000 . ? C4 C5 1.399(6) . ? C4 C9 1.408(5) . ? C5 C6 1.371(6) . ? C5 H5 0.9500 . ? C6 C7 1.354(6) . ? C6 H6 0.9500 . ? C7 C8 1.362(6) . ? C7 H7 0.9500 . ? C8 C9 1.430(6) . ? C8 H8 0.9500 . ? C9 C10 1.460(6) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.397(5) . ? C11 C16 1.399(5) . ? C12 C13 1.384(5) . ? C12 H12 0.9500 . ? C13 C14 1.372(5) . ? C13 H13 0.9500 . ? C14 C15 1.384(5) . ? C14 H14 0.9500 . ? C15 C16 1.398(5) . ? C15 H15 0.9500 . ? C16 C17 1.493(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.396(5) . ? C18 C23 1.400(5) . ? C18 N1 1.412(4) . ? C19 C20 1.373(5) . ? C19 H19 0.9500 . ? C20 C21 1.394(5) . ? C20 H20 0.9500 . ? C21 C22 1.374(5) . ? C21 H21 0.9500 . ? C22 C23 1.383(5) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? N1 O1 1.443(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C11 107.6(3) . . ? O1 C1 C2 101.8(3) . . ? C11 C1 C2 114.8(3) . . ? O1 C1 H1 110.7 . . ? C11 C1 H1 110.7 . . ? C2 C1 H1 110.7 . . ? C1 C2 C3 103.8(3) . . ? C1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? C1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? N1 C3 C4 110.8(3) . . ? N1 C3 C2 103.1(3) . . ? C4 C3 C2 113.5(3) . . ? N1 C3 H3 109.7 . . ? C4 C3 H3 109.7 . . ? C2 C3 H3 109.7 . . ? C5 C4 C9 117.9(4) . . ? C5 C4 C3 119.3(3) . . ? C9 C4 C3 122.7(3) . . ? C6 C5 C4 123.4(4) . . ? C6 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C7 C6 C5 118.4(5) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C6 C7 C8 121.5(4) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C7 C8 C9 121.4(4) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C4 C9 C8 117.3(4) . . ? C4 C9 C10 123.0(4) . . ? C8 C9 C10 119.7(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 120.5(3) . . ? C12 C11 C1 118.8(3) . . ? C16 C11 C1 120.7(3) . . ? C13 C12 C11 120.0(4) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.4(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.7(4) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 121.8(4) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C15 C16 C11 117.6(3) . . ? C15 C16 C17 120.1(3) . . ? C11 C16 C17 122.3(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 119.4(3) . . ? C19 C18 N1 119.6(3) . . ? C23 C18 N1 120.6(3) . . ? C20 C19 C18 119.9(4) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 121.0(4) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C22 C21 C20 118.8(3) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C23 121.5(4) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? C22 C23 C18 119.4(4) . . ? C22 C23 H23 120.3 . . ? C18 C23 H23 120.3 . . ? C18 N1 O1 112.7(3) . . ? C18 N1 C3 118.6(3) . . ? O1 N1 C3 108.7(2) . . ? N1 O1 C1 107.2(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 O1 C1 C2 C3 38.3(3) . . . . ? C11 C1 C2 C3 154.2(3) . . . . ? C1 C2 C3 N1 -26.0(3) . . . . ? C1 C2 C3 C4 -145.9(3) . . . . ? N1 C3 C4 C5 -46.8(4) . . . . ? C2 C3 C4 C5 68.6(4) . . . . ? N1 C3 C4 C9 135.6(3) . . . . ? C2 C3 C4 C9 -108.9(4) . . . . ? C9 C4 C5 C6 -2.0(6) . . . . ? C3 C4 C5 C6 -179.7(4) . . . . ? C4 C5 C6 C7 2.4(6) . . . . ? C5 C6 C7 C8 -1.8(6) . . . . ? C6 C7 C8 C9 0.9(6) . . . . ? C5 C4 C9 C8 1.0(5) . . . . ? C3 C4 C9 C8 178.6(3) . . . . ? C5 C4 C9 C10 179.2(4) . . . . ? C3 C4 C9 C10 -3.3(5) . . . . ? C7 C8 C9 C4 -0.5(5) . . . . ? C7 C8 C9 C10 -178.7(4) . . . . ? O1 C1 C11 C12 36.2(4) . . . . ? C2 C1 C11 C12 -76.3(4) . . . . ? O1 C1 C11 C16 -146.9(3) . . . . ? C2 C1 C11 C16 100.6(4) . . . . ? C16 C11 C12 C13 0.8(5) . . . . ? C1 C11 C12 C13 177.7(3) . . . . ? C11 C12 C13 C14 -0.6(6) . . . . ? C12 C13 C14 C15 0.6(5) . . . . ? C13 C14 C15 C16 -0.7(6) . . . . ? C14 C15 C16 C11 0.8(5) . . . . ? C14 C15 C16 C17 179.9(3) . . . . ? C12 C11 C16 C15 -0.9(5) . . . . ? C1 C11 C16 C15 -177.7(3) . . . . ? C12 C11 C16 C17 -179.9(4) . . . . ? C1 C11 C16 C17 3.2(5) . . . . ? C23 C18 C19 C20 0.3(6) . . . . ? N1 C18 C19 C20 173.4(3) . . . . ? C18 C19 C20 C21 1.3(6) . . . . ? C19 C20 C21 C22 -1.8(6) . . . . ? C20 C21 C22 C23 0.8(6) . . . . ? C21 C22 C23 C18 0.6(6) . . . . ? C19 C18 C23 C22 -1.2(5) . . . . ? N1 C18 C23 C22 -174.3(3) . . . . ? C19 C18 N1 O1 163.4(3) . . . . ? C23 C18 N1 O1 -23.6(4) . . . . ? C19 C18 N1 C3 34.8(5) . . . . ? C23 C18 N1 C3 -152.2(3) . . . . ? C4 C3 N1 C18 -103.6(3) . . . . ? C2 C3 N1 C18 134.6(3) . . . . ? C4 C3 N1 O1 125.9(3) . . . . ? C2 C3 N1 O1 4.1(3) . . . . ? C18 N1 O1 C1 -112.9(3) . . . . ? C3 N1 O1 C1 20.7(3) . . . . ? C11 C1 O1 N1 -157.5(2) . . . . ? C2 C1 O1 N1 -36.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.282 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.044 # Attachment 'pbcn.cif' data_pbcn _database_code_depnum_ccdc_archive 'CCDC 682984' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N O' _chemical_formula_weight 239.31 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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.772(8) _cell_length_b 6.743(4) _cell_length_c 24.033(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2556(2) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5156 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.52 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9698 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26298 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.55 _reflns_number_total 2941 _reflns_number_gt 2386 _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 'X-SEED (Barbour, 2001)' _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^)+(0.1229P)^2^+0.7678P] 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 2941 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0705 _refine_ls_wR_factor_ref 0.1870 _refine_ls_wR_factor_gt 0.1715 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.002 _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 0.87180(9) 0.2305(2) 0.62518(6) 0.0234(3) Uani 1 1 d . . . C2 C 0.90531(10) 0.1415(2) 0.67294(7) 0.0274(4) Uani 1 1 d . . . H2 H 0.9357 0.0203 0.6702 0.033 Uiso 1 1 calc R . . C3 C 0.89385(10) 0.2311(3) 0.72431(7) 0.0302(4) Uani 1 1 d . . . H3 H 0.9167 0.1707 0.7567 0.036 Uiso 1 1 calc R . . C4 C 0.84917(10) 0.4089(3) 0.72912(6) 0.0303(4) Uani 1 1 d . . . H4 H 0.8406 0.4677 0.7646 0.036 Uiso 1 1 calc R . . C5 C 0.81731(10) 0.4993(3) 0.68155(6) 0.0283(4) Uani 1 1 d . . . H5 H 0.7878 0.6216 0.6845 0.034 Uiso 1 1 calc R . . C6 C 0.82830(9) 0.4123(2) 0.62969(6) 0.0249(3) Uani 1 1 d . . . H6 H 0.8065 0.4751 0.5973 0.030 Uiso 1 1 calc R . . C7 C 0.89433(10) -0.0723(2) 0.56915(7) 0.0260(4) Uani 1 1 d . . . H7A H 0.8506 -0.1386 0.5921 0.031 Uiso 1 1 calc R . . H7B H 0.9511 -0.1172 0.5813 0.031 Uiso 1 1 calc R . . C8 C 0.88052(10) -0.1122(2) 0.50738(6) 0.0256(4) Uani 1 1 d . . . H8A H 0.8496 -0.2382 0.5015 0.031 Uiso 1 1 calc R . . H8B H 0.9352 -0.1177 0.4872 0.031 Uiso 1 1 calc R . . C9 C 0.82633(9) 0.0689(2) 0.48802(6) 0.0233(3) Uani 1 1 d . . . H9 H 0.7705 0.0193 0.4741 0.028 Uiso 1 1 calc R . . C10 C 0.86840(9) 0.1879(2) 0.44225(6) 0.0224(3) Uani 1 1 d . . . C11 C 0.86461(9) 0.1201(2) 0.38704(6) 0.0241(3) Uani 1 1 d . . . C12 C 0.90539(9) 0.2311(2) 0.34579(6) 0.0262(4) Uani 1 1 d . . . H12 H 0.9031 0.1868 0.3083 0.031 Uiso 1 1 calc R . . C13 C 0.94940(10) 0.4049(2) 0.35826(7) 0.0278(4) Uani 1 1 d . . . H13 H 0.9772 0.4772 0.3296 0.033 Uiso 1 1 calc R . . C14 C 0.95218(10) 0.4712(2) 0.41281(6) 0.0263(4) Uani 1 1 d . . . H14 H 0.9817 0.5898 0.4218 0.032 Uiso 1 1 calc R . . C15 C 0.91151(9) 0.3632(2) 0.45457(6) 0.0238(3) Uani 1 1 d . . . H15 H 0.9132 0.4097 0.4919 0.029 Uiso 1 1 calc R . . C16 C 0.81529(11) -0.0647(2) 0.37169(7) 0.0314(4) Uani 1 1 d . . . H16A H 0.8166 -0.0829 0.3312 0.047 Uiso 1 1 calc R . . H16B H 0.7564 -0.0507 0.3841 0.047 Uiso 1 1 calc R . . H16C H 0.8410 -0.1802 0.3898 0.047 Uiso 1 1 calc R . . N1 N 0.88672(8) 0.14467(18) 0.57244(5) 0.0233(3) Uani 1 1 d . . . O1 O 0.81204(6) 0.18574(15) 0.53726(4) 0.0240(3) 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 0.0188(7) 0.0262(7) 0.0253(7) 0.0007(6) 0.0009(5) -0.0021(6) C2 0.0237(8) 0.0296(8) 0.0290(8) 0.0028(6) 0.0000(6) 0.0013(6) C3 0.0266(8) 0.0389(9) 0.0251(8) 0.0049(6) -0.0013(6) -0.0015(7) C4 0.0283(8) 0.0380(9) 0.0248(8) -0.0041(6) -0.0008(6) -0.0030(7) C5 0.0254(8) 0.0297(8) 0.0296(8) -0.0044(6) -0.0016(6) -0.0002(6) C6 0.0231(7) 0.0260(7) 0.0257(7) 0.0004(6) -0.0019(6) -0.0011(6) C7 0.0259(8) 0.0226(7) 0.0293(8) 0.0020(6) 0.0024(6) 0.0038(6) C8 0.0258(8) 0.0217(7) 0.0294(8) 0.0001(6) 0.0020(6) 0.0013(5) C9 0.0219(7) 0.0228(7) 0.0252(8) -0.0037(5) 0.0008(5) -0.0007(5) C10 0.0197(6) 0.0224(7) 0.0251(7) -0.0002(5) -0.0003(5) 0.0029(5) C11 0.0204(7) 0.0248(7) 0.0272(7) -0.0010(6) -0.0012(6) 0.0028(6) C12 0.0250(7) 0.0294(8) 0.0241(7) -0.0005(6) 0.0004(6) 0.0043(6) C13 0.0249(8) 0.0294(8) 0.0292(8) 0.0053(6) 0.0006(6) 0.0020(6) C14 0.0240(7) 0.0229(7) 0.0320(8) 0.0009(6) -0.0017(6) -0.0007(6) C15 0.0215(7) 0.0246(7) 0.0254(7) -0.0019(6) -0.0015(5) 0.0015(6) C16 0.0353(9) 0.0316(8) 0.0274(8) -0.0056(6) -0.0012(6) -0.0055(7) N1 0.0205(6) 0.0242(7) 0.0253(7) 0.0015(5) -0.0023(5) 0.0017(5) O1 0.0216(6) 0.0269(6) 0.0236(6) -0.0025(4) -0.0021(4) 0.0039(4) _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 1.399(2) . ? C1 C6 1.409(2) . ? C1 N1 1.413(2) . ? C2 C3 1.387(2) . ? C2 H2 0.9500 . ? C3 C4 1.395(2) . ? C3 H3 0.9500 . ? C4 C5 1.389(2) . ? C4 H4 0.9500 . ? C5 C6 1.389(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.470(2) . ? C7 C8 1.524(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.561(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O1 1.4392(18) . ? C9 C10 1.515(2) . ? C9 H9 1.0000 . ? C10 C15 1.395(2) . ? C10 C11 1.405(2) . ? C11 C12 1.399(2) . ? C11 C16 1.515(2) . ? C12 C13 1.395(2) . ? C12 H12 0.9500 . ? C13 C14 1.386(2) . ? C13 H13 0.9500 . ? C14 C15 1.396(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1 O1 1.4761(16) . ? 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 119.61(14) . . ? C2 C1 N1 119.82(14) . . ? C6 C1 N1 120.44(13) . . ? C3 C2 C1 119.62(15) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 120.94(15) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.43(15) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C6 C5 C4 120.52(16) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 119.85(14) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? N1 C7 C8 102.49(12) . . ? N1 C7 H7A 111.3 . . ? C8 C7 H7A 111.3 . . ? N1 C7 H7B 111.3 . . ? C8 C7 H7B 111.3 . . ? H7A C7 H7B 109.2 . . ? C7 C8 C9 103.32(12) . . ? C7 C8 H8A 111.1 . . ? C9 C8 H8A 111.1 . . ? C7 C8 H8B 111.1 . . ? C9 C8 H8B 111.1 . . ? H8A C8 H8B 109.1 . . ? O1 C9 C10 112.07(12) . . ? O1 C9 C8 105.60(12) . . ? C10 C9 C8 113.01(12) . . ? O1 C9 H9 108.7 . . ? C10 C9 H9 108.7 . . ? C8 C9 H9 108.7 . . ? C15 C10 C11 119.80(14) . . ? C15 C10 C9 120.54(13) . . ? C11 C10 C9 119.66(14) . . ? C12 C11 C10 118.41(14) . . ? C12 C11 C16 120.25(14) . . ? C10 C11 C16 121.31(14) . . ? C13 C12 C11 121.75(14) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C14 C13 C12 119.33(14) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 119.84(14) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C10 C15 C14 120.86(14) . . ? C10 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C1 N1 C7 118.00(12) . . ? C1 N1 O1 107.70(11) . . ? C7 N1 O1 102.77(11) . . ? C9 O1 N1 104.09(10) . . ? 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 1.3(2) . . . . ? N1 C1 C2 C3 177.02(14) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C2 C3 C4 C5 -1.4(2) . . . . ? C3 C4 C5 C6 1.2(2) . . . . ? C4 C5 C6 C1 0.2(2) . . . . ? C2 C1 C6 C5 -1.5(2) . . . . ? N1 C1 C6 C5 -177.18(13) . . . . ? N1 C7 C8 C9 -25.60(14) . . . . ? C7 C8 C9 O1 -1.85(14) . . . . ? C7 C8 C9 C10 120.99(13) . . . . ? O1 C9 C10 C15 19.44(19) . . . . ? C8 C9 C10 C15 -99.72(16) . . . . ? O1 C9 C10 C11 -161.16(12) . . . . ? C8 C9 C10 C11 79.68(17) . . . . ? C15 C10 C11 C12 0.6(2) . . . . ? C9 C10 C11 C12 -178.80(13) . . . . ? C15 C10 C11 C16 -177.38(14) . . . . ? C9 C10 C11 C16 3.2(2) . . . . ? C10 C11 C12 C13 0.2(2) . . . . ? C16 C11 C12 C13 178.23(14) . . . . ? C11 C12 C13 C14 -0.7(2) . . . . ? C12 C13 C14 C15 0.4(2) . . . . ? C11 C10 C15 C14 -1.0(2) . . . . ? C9 C10 C15 C14 178.44(13) . . . . ? C13 C14 C15 C10 0.5(2) . . . . ? C2 C1 N1 C7 32.35(19) . . . . ? C6 C1 N1 C7 -151.96(14) . . . . ? C2 C1 N1 O1 147.98(13) . . . . ? C6 C1 N1 O1 -36.34(17) . . . . ? C8 C7 N1 C1 162.13(12) . . . . ? C8 C7 N1 O1 43.85(13) . . . . ? C10 C9 O1 N1 -94.76(13) . . . . ? C8 C9 O1 N1 28.69(13) . . . . ? C1 N1 O1 C9 -171.42(11) . . . . ? C7 N1 O1 C9 -46.13(13) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.695 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.090