# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Hu, Yuefei' 'Hu, Hongwen' 'Lu, Jun' 'Wang, Shaozhong' 'Wang, Cunde' 'Xu, Xuenong' _publ_contact_author_name 'Dr Yuefei Hu' _publ_contact_author_address ; Department of Chemistry Tsinghua University Beijing 100084 CHINA ; _publ_contact_author_email 'PYORG@NJU.EDU.CN' _publ_section_title ; Novel Preparation of Non-racemic 1-(alpha-Cycloaminobenzyl)-2-naphthols from Betti Base and Their Application as Chiral Ligands in the Asymmetric Addition of Diethylzinc to Aryl Aldehydes ; data_(I) _database_code_CSD 183965 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 N O' _chemical_formula_weight 317.41 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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' 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 8.2880(10) _cell_length_b 10.860(2) _cell_length_c 19.172(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1725.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.15 _cell_measurement_theta_max 16.76 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'North, Phillips & Mathews, 1968' _exptl_absorpt_correction_T_min 0.9639 _exptl_absorpt_correction_T_max 0.9781 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'CAD4' _diffrn_measurement_method 'omega/2-theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2203 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.17 _reflns_number_total 2203 _reflns_number_gt 1413 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4, Enraf-Nonius' _computing_cell_refinement 'CAD4, Enraf-Nonius' _computing_data_reduction 'Datared,Enraf-Nonius CAD-4 file' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows V1.05(Farrugia, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 'w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+0.2506P] 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 0.0150(18) _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 5(3) _refine_ls_number_reflns 2203 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0782 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8188(3) 1.0153(2) 1.02461(12) 0.0495(6) Uani 1 d . . . H1 H 0.7464 0.9508 1.0308 0.059 Uiso 1 calc R . . C2 C 0.8807(4) 1.0738(3) 1.08191(15) 0.0636(8) Uani 1 d . . . H2 H 0.8498 1.0491 1.1264 0.076 Uiso 1 calc R . . C3 C 0.9904(5) 1.1708(3) 1.07376(18) 0.0769(10) Uani 1 d . . . H3 H 1.0319 1.2103 1.1129 0.092 Uiso 1 calc R . . C4 C 1.0361(4) 1.2072(3) 1.00952(18) 0.0701(9) Uani 1 d . . . H4 H 1.1085 1.2721 1.0050 0.084 Uiso 1 calc R . . C5 C 1.0268(3) 1.1832(2) 0.88157(17) 0.0589(7) Uani 1 d . . . H5 H 1.0999 1.2475 0.8764 0.071 Uiso 1 calc R . . C6 C 0.9706(3) 1.1240(2) 0.82406(15) 0.0527(7) Uani 1 d . . . H6 H 1.0064 1.1475 0.7801 0.063 Uiso 1 calc R . . C7 C 0.8589(3) 1.0275(2) 0.83059(13) 0.0425(6) Uani 1 d . . . C8 C 0.8006(3) 0.9917(2) 0.89503(11) 0.0375(5) Uani 1 d . . . C9 C 0.9763(3) 1.1487(2) 0.94890(15) 0.0514(7) Uani 1 d . . . C10 C 0.8628(3) 1.0509(2) 0.95589(13) 0.0412(5) Uani 1 d . . . C11 C 0.6752(3) 0.8901(2) 0.90263(10) 0.0369(5) Uani 1 d . . . H11 H 0.6081 0.9099 0.9432 0.044 Uiso 1 calc R . . C12 C 0.7531(3) 0.7651(2) 0.91566(11) 0.0395(5) Uani 1 d . . . C13 C 0.6983(4) 0.6908(2) 0.96908(13) 0.0507(6) Uani 1 d . . . H13 H 0.6184 0.7196 0.9990 0.061 Uiso 1 calc R . . C14 C 0.7607(4) 0.5743(3) 0.97854(16) 0.0640(8) Uani 1 d . . . H14 H 0.7216 0.5248 1.0143 0.077 Uiso 1 calc R . . C15 C 0.8796(4) 0.5311(3) 0.93558(16) 0.0661(9) Uani 1 d . . . H15 H 0.9207 0.4522 0.9420 0.079 Uiso 1 calc R . . C16 C 0.9386(4) 0.6044(3) 0.88271(16) 0.0612(7) Uani 1 d . . . H16 H 1.0198 0.5754 0.8536 0.073 Uiso 1 calc R . . C17 C 0.8763(3) 0.7215(2) 0.87314(13) 0.0483(6) Uani 1 d . . . H17 H 0.9174 0.7715 0.8380 0.058 Uiso 1 calc R . . N1 N 0.5677(2) 0.88607(17) 0.84000(9) 0.0376(4) Uani 1 d . . . C18 C 0.4599(3) 0.7782(2) 0.84054(13) 0.0474(6) Uani 1 d . . . H18A H 0.3906 0.7818 0.8813 0.057 Uiso 1 calc R . . H18B H 0.5239 0.7036 0.8435 0.057 Uiso 1 calc R . . C19 C 0.3572(4) 0.7743(3) 0.77526(16) 0.0623(8) Uani 1 d . . . H19A H 0.4264 0.7631 0.7350 0.075 Uiso 1 calc R . . H19B H 0.2846 0.7044 0.7778 0.075 Uiso 1 calc R . . C20 C 0.2597(4) 0.8907(3) 0.76610(18) 0.0707(8) Uani 1 d . . . H20A H 0.1781 0.8957 0.8023 0.085 Uiso 1 calc R . . H20B H 0.2056 0.8892 0.7212 0.085 Uiso 1 calc R . . C21 C 0.3694(3) 1.0021(3) 0.77020(15) 0.0556(7) Uani 1 d . . . H21A H 0.3049 1.0766 0.7691 0.067 Uiso 1 calc R . . H21B H 0.4408 1.0031 0.7301 0.067 Uiso 1 calc R . . C22 C 0.4688(3) 0.9991(2) 0.83676(14) 0.0447(6) Uani 1 d . . . H22A H 0.5386 1.0707 0.8384 0.054 Uiso 1 calc R . . H22B H 0.3974 1.0022 0.8768 0.054 Uiso 1 calc R . . O1 O 0.8108(2) 0.97428(18) 0.76972(8) 0.0515(5) Uani 1 d . . . H1A H 0.7362 0.9266 0.7775 0.062 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0527(15) 0.0464(14) 0.0495(14) -0.0069(11) -0.0086(12) 0.0053(13) C2 0.078(2) 0.0605(17) 0.0518(15) -0.0132(14) -0.0153(16) 0.0131(18) C3 0.098(3) 0.0567(18) 0.076(2) -0.0244(17) -0.038(2) 0.006(2) C4 0.072(2) 0.0402(14) 0.099(2) -0.0133(17) -0.0323(19) -0.0024(16) C5 0.0457(15) 0.0400(14) 0.091(2) 0.0071(15) -0.0091(17) -0.0097(13) C6 0.0441(13) 0.0495(14) 0.0646(16) 0.0145(13) 0.0045(13) -0.0036(14) C7 0.0363(12) 0.0412(12) 0.0500(13) 0.0037(11) 0.0010(11) 0.0016(11) C8 0.0373(11) 0.0325(11) 0.0428(12) 0.0004(10) 0.0004(10) 0.0042(11) C9 0.0456(14) 0.0340(13) 0.0747(18) -0.0005(12) -0.0160(14) -0.0004(12) C10 0.0399(12) 0.0317(11) 0.0520(13) -0.0035(10) -0.0037(12) 0.0055(11) C11 0.0380(11) 0.0376(12) 0.0350(11) -0.0023(9) 0.0014(9) -0.0005(11) C12 0.0421(12) 0.0371(12) 0.0393(11) 0.0007(10) -0.0086(11) -0.0041(11) C13 0.0543(15) 0.0500(15) 0.0479(14) 0.0065(11) -0.0067(13) -0.0092(13) C14 0.073(2) 0.0533(16) 0.0656(17) 0.0224(14) -0.0196(17) -0.0191(17) C15 0.074(2) 0.0404(14) 0.084(2) 0.0092(14) -0.0322(19) 0.0037(16) C16 0.0629(17) 0.0496(15) 0.0712(18) -0.0045(15) -0.0107(16) 0.0127(15) C17 0.0527(15) 0.0445(13) 0.0478(14) 0.0022(11) -0.0036(13) 0.0029(14) N1 0.0373(10) 0.0350(9) 0.0405(10) -0.0025(9) -0.0027(9) -0.0006(9) C18 0.0471(14) 0.0394(12) 0.0558(15) -0.0017(12) -0.0049(13) -0.0038(12) C19 0.0623(18) 0.0508(15) 0.0738(18) -0.0092(14) -0.0261(16) -0.0066(15) C20 0.0565(17) 0.0637(18) 0.092(2) 0.0046(18) -0.0314(17) 0.0007(17) C21 0.0437(14) 0.0533(16) 0.0698(17) 0.0065(14) -0.0091(14) 0.0067(14) C22 0.0404(12) 0.0391(13) 0.0546(14) -0.0019(12) 0.0005(12) 0.0054(11) O1 0.0500(10) 0.0620(12) 0.0425(9) 0.0014(9) 0.0060(8) -0.0050(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 1.369(4) . ? C1 C10 1.421(3) . ? C1 H1 0.9300 . ? C2 C3 1.400(5) . ? C2 H2 0.9300 . ? C3 C4 1.348(5) . ? C3 H3 0.9300 . ? C4 C9 1.414(4) . ? C4 H4 0.9300 . ? C5 C6 1.359(4) . ? C5 C9 1.408(4) . ? C5 H5 0.9300 . ? C6 C7 1.404(3) . ? C6 H6 0.9300 . ? C7 O1 1.362(3) . ? C7 C8 1.382(3) . ? C8 C10 1.428(3) . ? C8 C11 1.522(3) . ? C9 C10 1.425(3) . ? C11 N1 1.496(3) . ? C11 C12 1.524(3) . ? C11 H11 0.9800 . ? C12 C13 1.381(3) . ? C12 C17 1.390(3) . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 C15 1.368(4) . ? C14 H14 0.9300 . ? C15 C16 1.379(4) . ? C15 H15 0.9300 . ? C16 C17 1.384(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? N1 C18 1.473(3) . ? N1 C22 1.477(3) . ? C18 C19 1.514(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.510(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.515(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.519(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? O1 H1A 0.8200 . ? 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 C10 121.5(3) . . ? C2 C1 H1 119.3 . . ? C10 C1 H1 119.3 . . ? C1 C2 C3 120.2(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C9 121.4(3) . . ? C3 C4 H4 119.3 . . ? C9 C4 H4 119.3 . . ? C6 C5 C9 121.1(2) . . ? C6 C5 H5 119.5 . . ? C9 C5 H5 119.5 . . ? C5 C6 C7 120.5(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? O1 C7 C8 123.0(2) . . ? O1 C7 C6 115.7(2) . . ? C8 C7 C6 121.3(2) . . ? C7 C8 C10 118.5(2) . . ? C7 C8 C11 121.9(2) . . ? C10 C8 C11 119.60(19) . . ? C5 C9 C4 122.0(3) . . ? C5 C9 C10 118.7(2) . . ? C4 C9 C10 119.3(3) . . ? C1 C10 C9 117.3(2) . . ? C1 C10 C8 122.9(2) . . ? C9 C10 C8 119.8(2) . . ? N1 C11 C8 110.56(17) . . ? N1 C11 C12 110.94(17) . . ? C8 C11 C12 111.88(18) . . ? N1 C11 H11 107.8 . . ? C8 C11 H11 107.8 . . ? C12 C11 H11 107.8 . . ? C13 C12 C17 118.5(2) . . ? C13 C12 C11 120.2(2) . . ? C17 C12 C11 121.2(2) . . ? C14 C13 C12 120.7(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 120.4(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.0(3) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 119.7(3) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C12 120.6(3) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C18 N1 C22 108.94(18) . . ? C18 N1 C11 112.28(17) . . ? C22 N1 C11 109.86(17) . . ? N1 C18 C19 110.9(2) . . ? N1 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.0 . . ? C20 C19 C18 112.0(2) . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19B 109.2 . . ? C18 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C19 C20 C21 109.9(2) . . ? C19 C20 H20A 109.7 . . ? C21 C20 H20A 109.7 . . ? C19 C20 H20B 109.7 . . ? C21 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C20 C21 C22 110.6(2) . . ? C20 C21 H21A 109.5 . . ? C22 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 108.1 . . ? N1 C22 C21 110.7(2) . . ? N1 C22 H22A 109.5 . . ? C21 C22 H22A 109.5 . . ? N1 C22 H22B 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C7 O1 H1A 109.5 . . ? 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 C10 C1 C2 C3 -0.3(4) . . . . ? C1 C2 C3 C4 -0.1(5) . . . . ? C2 C3 C4 C9 -0.4(5) . . . . ? C9 C5 C6 C7 0.7(4) . . . . ? C5 C6 C7 O1 -179.8(2) . . . . ? C5 C6 C7 C8 1.4(4) . . . . ? O1 C7 C8 C10 178.0(2) . . . . ? C6 C7 C8 C10 -3.2(3) . . . . ? O1 C7 C8 C11 -0.8(3) . . . . ? C6 C7 C8 C11 177.9(2) . . . . ? C6 C5 C9 C4 178.5(3) . . . . ? C6 C5 C9 C10 -0.7(4) . . . . ? C3 C4 C9 C5 -178.0(3) . . . . ? C3 C4 C9 C10 1.3(4) . . . . ? C2 C1 C10 C9 1.1(4) . . . . ? C2 C1 C10 C8 180.0(2) . . . . ? C5 C9 C10 C1 177.7(2) . . . . ? C4 C9 C10 C1 -1.6(4) . . . . ? C5 C9 C10 C8 -1.2(3) . . . . ? C4 C9 C10 C8 179.5(2) . . . . ? C7 C8 C10 C1 -175.7(2) . . . . ? C11 C8 C10 C1 3.2(3) . . . . ? C7 C8 C10 C9 3.2(3) . . . . ? C11 C8 C10 C9 -178.0(2) . . . . ? C7 C8 C11 N1 -30.4(3) . . . . ? C10 C8 C11 N1 150.78(19) . . . . ? C7 C8 C11 C12 93.8(2) . . . . ? C10 C8 C11 C12 -85.0(2) . . . . ? N1 C11 C12 C13 -104.5(2) . . . . ? C8 C11 C12 C13 131.5(2) . . . . ? N1 C11 C12 C17 73.4(3) . . . . ? C8 C11 C12 C17 -50.6(3) . . . . ? C17 C12 C13 C14 -2.2(4) . . . . ? C11 C12 C13 C14 175.8(2) . . . . ? C12 C13 C14 C15 0.8(4) . . . . ? C13 C14 C15 C16 0.4(4) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? C15 C16 C17 C12 -1.0(4) . . . . ? C13 C12 C17 C16 2.3(4) . . . . ? C11 C12 C17 C16 -175.7(2) . . . . ? C8 C11 N1 C18 171.80(18) . . . . ? C12 C11 N1 C18 47.1(2) . . . . ? C8 C11 N1 C22 -66.8(2) . . . . ? C12 C11 N1 C22 168.48(18) . . . . ? C22 N1 C18 C19 60.2(3) . . . . ? C11 N1 C18 C19 -177.9(2) . . . . ? N1 C18 C19 C20 -56.7(3) . . . . ? C18 C19 C20 C21 52.6(4) . . . . ? C19 C20 C21 C22 -53.3(3) . . . . ? C18 N1 C22 C21 -61.6(2) . . . . ? C11 N1 C22 C21 175.03(19) . . . . ? C20 C21 C22 N1 58.8(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.17 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.175 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.033 data_lu0112 _database_code_CSD 183966 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 N O' _chemical_formula_weight 314.39 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 ? _symmetry_space_group_name_H-M ? 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 9.813(4) _cell_length_b 10.354(3) _cell_length_c 16.491(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1675.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.12 _cell_measurement_theta_max 14.60 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type 'North, Phillips & Mathews, 1968' _exptl_absorpt_correction_T_min 0.9703 _exptl_absorpt_correction_T_max 0.9776 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'CAD4' _diffrn_measurement_method 'omega/2-theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 100 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% ? _diffrn_reflns_number 2135 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.17 _reflns_number_total 2135 _reflns_number_gt 1384 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4, Enraf-Nonius' _computing_cell_refinement 'CAD4, Enraf-Nonius' _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows V1.05(Farrugia, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 'w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.2770P] 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 0.0143(17) _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 -10(3) _refine_ls_number_reflns 2135 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0009(3) 0.4151(3) 0.22956(15) 0.0463(6) Uani 1 d . . . H1 H 0.0566 0.3522 0.2508 0.056 Uiso 1 calc R . . C2 C -0.1326(3) 0.4230(3) 0.25647(18) 0.0576(8) Uani 1 d . . . H2 H -0.1639 0.3649 0.2952 0.069 Uiso 1 calc R . . C3 C -0.2204(3) 0.5175(3) 0.22625(19) 0.0621(8) Uani 1 d . . . H3 H -0.3099 0.5218 0.2446 0.075 Uiso 1 calc R . . C4 C -0.1753(3) 0.6034(3) 0.17009(17) 0.0559(8) Uani 1 d . . . H4 H -0.2344 0.6665 0.1507 0.067 Uiso 1 calc R . . C5 C 0.0074(3) 0.6859(3) 0.08156(16) 0.0470(7) Uani 1 d . . . H5 H -0.0498 0.7511 0.0630 0.056 Uiso 1 calc R . . C6 C 0.1356(3) 0.6763(2) 0.05139(16) 0.0457(6) Uani 1 d . . . H6 H 0.1651 0.7338 0.0118 0.055 Uiso 1 calc R . . C7 C 0.2241(2) 0.5791(2) 0.07989(15) 0.0384(6) Uani 1 d . . . C8 C 0.1849(2) 0.4939(2) 0.13859(14) 0.0355(5) Uani 1 d . . . C9 C -0.0402(3) 0.5987(3) 0.14050(15) 0.0429(6) Uani 1 d . . . C10 C 0.0494(2) 0.5016(3) 0.16978(14) 0.0373(5) Uani 1 d . . . C11 C 0.2850(2) 0.3905(2) 0.16510(14) 0.0357(5) Uani 1 d . . . H11 H 0.2329 0.3110 0.1742 0.043 Uiso 1 calc R . . C12 C 0.3595(2) 0.4216(3) 0.24378(14) 0.0367(5) Uani 1 d . . . C13 C 0.3465(3) 0.5386(3) 0.28300(16) 0.0484(7) Uani 1 d . . . H13 H 0.2889 0.6015 0.2619 0.058 Uiso 1 calc R . . C14 C 0.4189(3) 0.5635(3) 0.35389(16) 0.0569(8) Uani 1 d . . . H14 H 0.4099 0.6431 0.3794 0.068 Uiso 1 calc R . . C15 C 0.5023(3) 0.4723(3) 0.38601(16) 0.0591(8) Uani 1 d . . . H15 H 0.5502 0.4894 0.4335 0.071 Uiso 1 calc R . . C16 C 0.5160(3) 0.3543(3) 0.34817(17) 0.0570(8) Uani 1 d . . . H16 H 0.5725 0.2914 0.3703 0.068 Uiso 1 calc R . . C17 C 0.4455(3) 0.3295(3) 0.27722(16) 0.0463(6) Uani 1 d . . . H17 H 0.4558 0.2501 0.2516 0.056 Uiso 1 calc R . . O1 O 0.34912(17) 0.57680(17) 0.04290(11) 0.0473(5) Uani 1 d . . . C18 C 0.3208(3) 0.2902(3) 0.03275(15) 0.0443(6) Uani 1 d . . . H18A H 0.2437 0.3382 0.0116 0.053 Uiso 1 calc R . . H18B H 0.2870 0.2087 0.0536 0.053 Uiso 1 calc R . . C19 C 0.4207(3) 0.2642(3) -0.03526(16) 0.0523(7) Uani 1 d . . . H19A H 0.4914 0.2061 -0.0162 0.063 Uiso 1 calc R . . H19B H 0.3737 0.2224 -0.0799 0.063 Uiso 1 calc R . . C20 C 0.4847(3) 0.3881(3) -0.06460(16) 0.0563(8) Uani 1 d . . . H20A H 0.4158 0.4418 -0.0900 0.068 Uiso 1 calc R . . H20B H 0.5540 0.3688 -0.1047 0.068 Uiso 1 calc R . . C21 C 0.5484(3) 0.4603(3) 0.00610(16) 0.0498(7) Uani 1 d . . . H21A H 0.6252 0.4113 0.0267 0.060 Uiso 1 calc R . . H21B H 0.5822 0.5431 -0.0127 0.060 Uiso 1 calc R . . C22 C 0.4467(3) 0.4819(2) 0.07397(16) 0.0409(6) Uani 1 d . . . H22 H 0.4947 0.5197 0.1204 0.049 Uiso 1 calc R . . N1 N 0.38375(19) 0.36399(19) 0.09938(11) 0.0361(5) Uani 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 0.0434(13) 0.0510(15) 0.0444(14) 0.0043(13) 0.0039(13) 0.0006(14) C2 0.0466(15) 0.073(2) 0.0532(16) 0.0075(16) 0.0118(14) -0.0034(16) C3 0.0376(15) 0.084(2) 0.0647(19) 0.0012(19) 0.0101(14) 0.0040(16) C4 0.0423(14) 0.068(2) 0.0575(16) 0.0001(16) 0.0025(14) 0.0135(15) C5 0.0473(15) 0.0443(14) 0.0495(15) 0.0030(13) -0.0019(14) 0.0122(13) C6 0.0525(16) 0.0386(14) 0.0459(14) 0.0042(12) 0.0021(13) 0.0022(13) C7 0.0373(12) 0.0362(13) 0.0418(13) -0.0038(11) 0.0008(11) -0.0003(11) C8 0.0356(12) 0.0355(12) 0.0353(12) -0.0015(11) -0.0001(11) 0.0000(11) C9 0.0420(13) 0.0456(14) 0.0412(13) -0.0064(12) -0.0018(12) 0.0043(12) C10 0.0363(12) 0.0407(13) 0.0350(12) -0.0052(11) -0.0018(11) -0.0021(12) C11 0.0327(12) 0.0347(13) 0.0396(12) 0.0018(11) 0.0005(11) -0.0039(11) C12 0.0344(12) 0.0408(13) 0.0350(12) 0.0043(11) 0.0037(10) -0.0037(11) C13 0.0570(16) 0.0451(14) 0.0432(14) -0.0026(12) -0.0010(14) 0.0044(14) C14 0.0725(19) 0.0557(17) 0.0426(14) -0.0052(15) -0.0008(15) -0.0044(17) C15 0.0650(18) 0.075(2) 0.0373(14) 0.0037(15) -0.0065(15) -0.0174(17) C16 0.0537(17) 0.0637(18) 0.0537(16) 0.0183(16) -0.0098(15) -0.0019(16) C17 0.0472(15) 0.0413(14) 0.0505(15) 0.0037(12) 0.0000(13) -0.0004(13) O1 0.0420(10) 0.0419(10) 0.0580(10) 0.0107(9) 0.0115(9) 0.0035(9) C18 0.0431(13) 0.0426(14) 0.0472(14) -0.0065(12) -0.0012(13) 0.0003(12) C19 0.0537(16) 0.0587(17) 0.0444(14) -0.0100(14) 0.0009(14) 0.0044(14) C20 0.0555(17) 0.0688(19) 0.0445(15) 0.0037(14) 0.0118(14) 0.0126(16) C21 0.0399(14) 0.0530(16) 0.0566(15) 0.0073(14) 0.0108(13) 0.0027(13) C22 0.0352(12) 0.0379(13) 0.0497(14) -0.0006(12) 0.0025(12) -0.0009(11) N1 0.0340(10) 0.0352(10) 0.0391(10) 0.0004(9) 0.0013(9) 0.0000(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 C1 C2 1.369(4) . ? C1 C10 1.420(4) . ? C1 H1 0.9300 . ? C2 C3 1.396(4) . ? C2 H2 0.9300 . ? C3 C4 1.358(4) . ? C3 H3 0.9300 . ? C4 C9 1.413(4) . ? C4 H4 0.9300 . ? C5 C6 1.356(4) . ? C5 C9 1.406(4) . ? C5 H5 0.9300 . ? C6 C7 1.410(3) . ? C6 H6 0.9300 . ? C7 C8 1.365(3) . ? C7 O1 1.370(3) . ? C8 C10 1.428(3) . ? C8 C11 1.517(3) . ? C9 C10 1.420(4) . ? C11 N1 1.479(3) . ? C11 C12 1.524(3) . ? C11 H11 0.9800 . ? C12 C13 1.379(4) . ? C12 C17 1.387(3) . ? C13 C14 1.392(4) . ? C13 H13 0.9300 . ? C14 C15 1.357(4) . ? C14 H14 0.9300 . ? C15 C16 1.379(4) . ? C15 H15 0.9300 . ? C16 C17 1.383(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? O1 C22 1.464(3) . ? C18 N1 1.474(3) . ? C18 C19 1.514(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.508(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.520(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.516(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N1 1.431(3) . ? C22 H22 0.9800 . ? 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 C10 121.0(3) . . ? C2 C1 H1 119.5 . . ? C10 C1 H1 119.5 . . ? C1 C2 C3 120.6(3) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C9 121.2(3) . . ? C3 C4 H4 119.4 . . ? C9 C4 H4 119.4 . . ? C6 C5 C9 121.0(2) . . ? C6 C5 H5 119.5 . . ? C9 C5 H5 119.5 . . ? C5 C6 C7 120.1(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 O1 123.8(2) . . ? C8 C7 C6 121.6(2) . . ? O1 C7 C6 114.6(2) . . ? C7 C8 C10 118.8(2) . . ? C7 C8 C11 118.6(2) . . ? C10 C8 C11 122.6(2) . . ? C5 C9 C4 121.9(3) . . ? C5 C9 C10 118.9(2) . . ? C4 C9 C10 119.2(3) . . ? C9 C10 C1 117.9(2) . . ? C9 C10 C8 119.6(2) . . ? C1 C10 C8 122.5(2) . . ? N1 C11 C8 110.11(19) . . ? N1 C11 C12 110.42(18) . . ? C8 C11 C12 114.0(2) . . ? N1 C11 H11 107.3 . . ? C8 C11 H11 107.3 . . ? C12 C11 H11 107.3 . . ? C13 C12 C17 118.3(2) . . ? C13 C12 C11 122.7(2) . . ? C17 C12 C11 119.0(2) . . ? C12 C13 C14 120.6(3) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.9(3) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 119.9(3) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C12 120.9(3) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? C7 O1 C22 116.20(19) . . ? N1 C18 C19 111.9(2) . . ? N1 C18 H18A 109.2 . . ? C19 C18 H18A 109.2 . . ? N1 C18 H18B 109.2 . . ? C19 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C20 C19 C18 110.8(2) . . ? C20 C19 H19A 109.5 . . ? C18 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? C19 C20 C21 110.1(2) . . ? C19 C20 H20A 109.6 . . ? C21 C20 H20A 109.6 . . ? C19 C20 H20B 109.6 . . ? C21 C20 H20B 109.6 . . ? H20A C20 H20B 108.2 . . ? C22 C21 C20 111.6(2) . . ? C22 C21 H21A 109.3 . . ? C20 C21 H21A 109.3 . . ? C22 C21 H21B 109.3 . . ? C20 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? N1 C22 O1 113.12(19) . . ? N1 C22 C21 112.0(2) . . ? O1 C22 C21 105.7(2) . . ? N1 C22 H22 108.6 . . ? O1 C22 H22 108.6 . . ? C21 C22 H22 108.6 . . ? C22 N1 C18 113.9(2) . . ? C22 N1 C11 109.82(18) . . ? C18 N1 C11 111.58(18) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.17 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.179 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.035