# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Prandi, Cristina' _publ_contact_author_email cristina.prandi@unito.it _publ_section_title ; Superbase Promoted Synthesis of Dienamides as Useful Intermediates for the Synthesis of a-Ketoamides, g-Lactams and Cyclic Iminoethers ; loop_ _publ_author_name C.Prandi A.Deagostino M.Blangetti P.Venturello G.Gervasio ; D.Marabello ; # Attachment 'compound5i.cif' data_compound5a _database_code_depnum_ccdc_archive 'CCDC 776929' #TrackingRef 'compound5i.cif' _audit_creation_date ; 'Thu Mar 04 15:55:25 2010' ; _audit_creation_method ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _cell_length_a 8.8274(5) _cell_length_b 13.2339(6) _cell_length_c 12.3855(7) _cell_angle_alpha 90.0 _cell_angle_beta 103.267(6) _cell_angle_gamma 90.0 _cell_volume 1408.28(12) _cell_formula_units_Z 4.00000 _cell_measurement_reflns_used 2797 _cell_measurement_temperature 293(2) _cell_measurement_theta_min 3.3732 _cell_measurement_theta_max 23.2023 _exptl_absorpt_correction_T_min 0.98510 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_detector_area_resol_mean 10.2890 _diffrn_reflns_number 12381 _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 -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.3732 _diffrn_reflns_theta_max 23.2023 _diffrn_orient_matrix_UB_11 -0.0424877000 _diffrn_orient_matrix_UB_12 0.0179367000 _diffrn_orient_matrix_UB_13 0.0382426000 _diffrn_orient_matrix_UB_21 -0.0661917000 _diffrn_orient_matrix_UB_22 -0.0275834000 _diffrn_orient_matrix_UB_23 -0.0282571000 _diffrn_orient_matrix_UB_31 0.0251215000 _diffrn_orient_matrix_UB_32 -0.0423105000 _diffrn_orient_matrix_UB_33 0.0346430000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -10.00 34.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ frames - 17.7068 69.0000 2.0000 44 #__ type_ start__ end____ width___ exp.time_ 2 omega -12.00 45.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ frames - 17.7068 69.0000 95.0000 57 #__ type_ start__ end____ width___ exp.time_ 3 omega -41.00 20.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ frames - 17.7068 -37.0000 90.0000 61 #__ type_ start__ end____ width___ exp.time_ 4 omega -53.00 28.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ frames - 17.7068 -37.0000 -30.0000 81 #__ type_ start__ end____ width___ exp.time_ 5 omega -51.00 30.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ frames - 17.7068 -50.0000 -130.0000 81 #__ type_ start__ end____ width___ exp.time_ 6 omega -12.00 56.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ frames - 17.7068 69.0000 -141.0000 68 #__ type_ start__ end____ width___ exp.time_ 7 omega -10.00 34.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ frames - 17.7068 69.0000 2.0000 44 #__ type_ start__ end____ width___ exp.time_ 8 omega -12.00 45.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ frames - 17.7068 69.0000 95.0000 57 ; _diffrn_measurement_method '\w scans' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 N O2' _chemical_formula_weight 267.32 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 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' _exptl_crystal_description prism _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.083 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0480 _reflns_number_total 2012 _reflns_number_gt 1233 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1044P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2012 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1050 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1837 _refine_ls_wR_factor_gt 0.1687 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.9662(3) 0.90634(17) 0.8096(2) 0.0487(7) Uani 1 1 d . A . C1 C 0.8279(4) 0.9292(3) 0.8056(3) 0.0605(9) Uani 1 1 d . . . O1A O 0.7519(4) 0.9115(3) 0.8893(3) 0.0583(13) Uiso 0.624(6) 1 d P A 1 C2A C 0.6012(7) 0.9650(4) 0.8640(5) 0.0640(18) Uiso 0.624(6) 1 d P A 1 H2AA H 0.5972 1.0128 0.9237 0.077 Uiso 0.624(6) 1 calc PR A 1 C3A C 0.4760(8) 0.8893(5) 0.8553(7) 0.0749(19) Uiso 0.624(6) 1 d P A 1 H3AA H 0.4857 0.8563 0.9255 0.112 Uiso 0.624(6) 1 calc PR A 1 H3AB H 0.4842 0.8402 0.7999 0.112 Uiso 0.624(6) 1 calc PR A 1 H3AC H 0.3767 0.9224 0.8347 0.112 Uiso 0.624(6) 1 calc PR A 1 C5A C 0.6023(7) 1.0204(5) 0.7619(5) 0.0612(16) Uiso 0.624(6) 1 d P A 1 H5AA H 0.5248 1.0645 0.7263 0.073 Uiso 0.624(6) 1 calc PR A 1 O1B O 0.7281(7) 0.8592(5) 0.8465(5) 0.053(2) Uiso 0.376(6) 1 d P A 2 C2B C 0.5638(12) 0.8912(7) 0.8033(8) 0.060(3) Uiso 0.376(6) 1 d P A 2 H2BA H 0.5037 0.8342 0.7648 0.072 Uiso 0.376(6) 1 calc PR A 2 C3B C 0.4981(13) 0.9210(8) 0.9072(10) 0.073(3) Uiso 0.376(6) 1 d P A 2 H3BA H 0.4930 0.8619 0.9512 0.110 Uiso 0.376(6) 1 calc PR A 2 H3BB H 0.3959 0.9493 0.8827 0.110 Uiso 0.376(6) 1 calc PR A 2 H3BC H 0.5657 0.9700 0.9510 0.110 Uiso 0.376(6) 1 calc PR A 2 C5B C 0.5752(13) 0.9716(8) 0.7208(8) 0.068(3) Uiso 0.376(6) 1 d P A 2 H5BB H 0.4905 0.9998 0.6712 0.082 Uiso 0.376(6) 1 calc PR A 2 C6 C 0.7293(4) 0.9985(3) 0.7281(3) 0.0602(9) Uani 1 1 d . A . O2 O 0.7883(3) 1.04228(15) 0.65113(19) 0.0621(7) Uani 1 1 d . . . C7 C 0.6809(5) 1.1099(3) 0.5781(4) 0.0836(13) Uani 1 1 d . A . H7A H 0.5863 1.0737 0.5443 0.100 Uiso 1 1 calc R . . H7B H 0.6534 1.1657 0.6207 0.100 Uiso 1 1 calc R . . C8 C 0.7517(5) 1.1476(3) 0.4941(4) 0.0951(14) Uani 1 1 d . . . H8A H 0.6811 1.1927 0.4466 0.143 Uiso 1 1 calc R A . H8B H 0.7767 1.0923 0.4512 0.143 Uiso 1 1 calc R . . H8C H 0.8452 1.1834 0.5279 0.143 Uiso 1 1 calc R . . C9 C 1.0512(4) 0.8401(2) 0.8924(3) 0.0525(9) Uani 1 1 d . . . C10 C 1.0580(5) 0.8532(3) 1.0029(3) 0.0734(11) Uani 1 1 d . A . H10A H 0.9999 0.9043 1.0255 0.088 Uiso 1 1 calc R . . C11 C 1.1505(6) 0.7913(4) 1.0820(4) 0.0990(16) Uani 1 1 d . . . H11A H 1.1538 0.8018 1.1567 0.119 Uiso 1 1 calc R A . C12 C 1.2345(6) 0.7169(4) 1.0523(5) 0.107(2) Uani 1 1 d . A . H12A H 1.2949 0.6761 1.1067 0.128 Uiso 1 1 calc R . . C13 C 1.2334(4) 0.6992(3) 0.9400(5) 0.0784(13) Uani 1 1 d . . . C14 C 1.1400(4) 0.7634(2) 0.8574(3) 0.0577(10) Uani 1 1 d . A . C15 C 1.1408(4) 0.7468(2) 0.7461(4) 0.0682(11) Uani 1 1 d . . . H15A H 1.0811 0.7882 0.6920 0.082 Uiso 1 1 calc R A . C16 C 1.2280(4) 0.6703(3) 0.7146(5) 0.0925(14) Uani 1 1 d . A . H16A H 1.2272 0.6599 0.6402 0.111 Uiso 1 1 calc R . . C17 C 1.3191(5) 0.6076(3) 0.7983(7) 0.116(2) Uani 1 1 d . . . H17A H 1.3782 0.5556 0.7785 0.139 Uiso 1 1 calc R A . C18 C 1.3204(6) 0.6233(4) 0.9053(7) 0.119(2) Uani 1 1 d . A . H18A H 1.3818 0.5818 0.9584 0.143 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0450(17) 0.0443(14) 0.0533(16) 0.0053(11) 0.0039(13) 0.0029(12) C1 0.052(2) 0.068(2) 0.061(2) 0.0140(17) 0.0128(19) 0.0074(18) C6 0.053(2) 0.067(2) 0.063(2) 0.0157(18) 0.0199(18) 0.0140(17) O2 0.0603(15) 0.0528(13) 0.0706(15) 0.0134(12) 0.0097(13) 0.0207(11) C7 0.073(3) 0.067(2) 0.106(3) 0.031(2) 0.012(3) 0.028(2) C8 0.099(3) 0.075(3) 0.106(3) 0.029(2) 0.011(3) 0.026(2) C9 0.0458(19) 0.0443(18) 0.061(2) 0.0131(16) -0.0017(17) -0.0105(15) C10 0.083(3) 0.062(2) 0.064(3) 0.0127(18) -0.006(2) -0.020(2) C11 0.115(4) 0.083(3) 0.076(3) 0.030(3) -0.027(3) -0.034(3) C12 0.082(3) 0.080(3) 0.120(4) 0.058(3) -0.057(3) -0.038(3) C13 0.038(2) 0.046(2) 0.132(4) 0.030(2) -0.021(2) -0.0098(17) C14 0.0384(19) 0.0438(18) 0.082(3) 0.0136(18) -0.0051(18) -0.0095(15) C15 0.040(2) 0.049(2) 0.113(3) 0.009(2) 0.013(2) 0.0040(16) C16 0.054(2) 0.063(2) 0.162(4) -0.009(3) 0.029(3) -0.001(2) C17 0.040(3) 0.050(3) 0.253(8) 0.007(4) 0.022(4) 0.006(2) C18 0.045(3) 0.054(3) 0.233(7) 0.036(4) -0.021(4) -0.007(2) _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 N1 C1 1.247(4) . ? N1 C9 1.424(4) . ? C1 O1A 1.378(5) . ? C1 O1B 1.448(6) . ? C1 C6 1.461(5) . ? O1A C2A 1.475(6) . ? C2A C5A 1.464(8) . ? C2A C3A 1.477(9) . ? C2A H2AA 0.9800 . ? C3A H3AA 0.9600 . ? C3A H3AB 0.9600 . ? C3A H3AC 0.9600 . ? C5A C6 1.316(6) . ? C5A H5AA 0.9300 . ? O1B C2B 1.488(11) . ? C2B C5B 1.494(13) . ? C2B C3B 1.579(16) . ? C2B H2BA 0.9800 . ? C3B H3BA 0.9600 . ? C3B H3BB 0.9600 . ? C3B H3BC 0.9600 . ? C5B C6 1.389(11) . ? C5B H5BB 0.9300 . ? C6 O2 1.321(4) . ? O2 C7 1.458(4) . ? C7 C8 1.421(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.367(5) . ? C9 C14 1.410(5) . ? C10 C11 1.389(6) . ? C10 H10A 0.9300 . ? C11 C12 1.334(7) . ? C11 H11A 0.9300 . ? C12 C13 1.409(7) . ? C12 H12A 0.9300 . ? C13 C18 1.392(8) . ? C13 C14 1.435(5) . ? C14 C15 1.398(5) . ? C15 C16 1.381(5) . ? C15 H15A 0.9300 . ? C16 C17 1.423(8) . ? C16 H16A 0.9300 . ? C17 C18 1.338(7) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? 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 121.8(3) . . ? N1 C1 O1A 124.7(3) . . ? N1 C1 O1B 119.9(3) . . ? O1A C1 O1B 35.7(2) . . ? N1 C1 C6 127.5(3) . . ? O1A C1 C6 106.3(3) . . ? O1B C1 C6 108.2(3) . . ? C1 O1A C2A 109.3(3) . . ? C5A C2A O1A 103.9(5) . . ? C5A C2A C3A 115.4(5) . . ? O1A C2A C3A 108.3(5) . . ? C5A C2A H2AA 109.7 . . ? O1A C2A H2AA 109.7 . . ? C3A C2A H2AA 109.7 . . ? C2A C3A H3AA 109.5 . . ? C2A C3A H3AB 109.5 . . ? H3AA C3A H3AB 109.5 . . ? C2A C3A H3AC 109.5 . . ? H3AA C3A H3AC 109.5 . . ? H3AB C3A H3AC 109.5 . . ? C6 C5A C2A 109.8(5) . . ? C6 C5A H5AA 125.1 . . ? C2A C5A H5AA 125.1 . . ? C1 O1B C2B 108.3(5) . . ? O1B C2B C5B 103.6(8) . . ? O1B C2B C3B 106.7(7) . . ? C5B C2B C3B 118.3(8) . . ? O1B C2B H2BA 109.3 . . ? C5B C2B H2BA 109.3 . . ? C3B C2B H2BA 109.3 . . ? C2B C3B H3BA 109.5 . . ? C2B C3B H3BB 109.5 . . ? H3BA C3B H3BB 109.5 . . ? C2B C3B H3BC 109.5 . . ? H3BA C3B H3BC 109.5 . . ? H3BB C3B H3BC 109.5 . . ? C6 C5B C2B 110.9(8) . . ? C6 C5B H5BB 124.6 . . ? C2B C5B H5BB 124.6 . . ? C5A C6 O2 129.7(4) . . ? C5A C6 C5B 35.3(4) . . ? O2 C6 C5B 127.4(5) . . ? C5A C6 C1 110.6(4) . . ? O2 C6 C1 118.4(3) . . ? C5B C6 C1 108.0(5) . . ? C6 O2 C7 114.2(3) . . ? C8 C7 O2 109.7(3) . . ? C8 C7 H7A 109.7 . . ? O2 C7 H7A 109.7 . . ? C8 C7 H7B 109.7 . . ? O2 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 119.9(3) . . ? C10 C9 N1 122.5(3) . . ? C14 C9 N1 117.4(3) . . ? C9 C10 C11 121.0(4) . . ? C9 C10 H10A 119.5 . . ? C11 C10 H10A 119.5 . . ? C12 C11 C10 121.0(5) . . ? C12 C11 H11A 119.5 . . ? C10 C11 H11A 119.5 . . ? C11 C12 C13 121.1(4) . . ? C11 C12 H12A 119.5 . . ? C13 C12 H12A 119.5 . . ? C18 C13 C12 123.1(5) . . ? C18 C13 C14 118.3(5) . . ? C12 C13 C14 118.6(4) . . ? C15 C14 C9 123.0(3) . . ? C15 C14 C13 118.5(4) . . ? C9 C14 C13 118.5(4) . . ? C16 C15 C14 121.6(4) . . ? C16 C15 H15A 119.2 . . ? C14 C15 H15A 119.2 . . ? C15 C16 C17 118.7(5) . . ? C15 C16 H16A 120.7 . . ? C17 C16 H16A 120.7 . . ? C18 C17 C16 120.4(5) . . ? C18 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? C17 C18 C13 122.5(5) . . ? C17 C18 H18A 118.7 . . ? C13 C18 H18A 118.7 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.300 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.036 # Attachment 'compound5f.CIF' data_compound5d _database_code_depnum_ccdc_archive 'CCDC 776930' #TrackingRef 'compound5f.CIF' _audit_creation_date ; 'Sun Jan 24 07:24:21 2010' ; _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _cell_measurement_temperature 293(2) _diffrn_ambient_temperature 293(2) _cell_length_a 14.0009(6) _cell_length_b 8.4953(3) _cell_length_c 26.8700(12) _cell_angle_alpha 90.0 _cell_angle_beta 97.115(4) _cell_angle_gamma 90.0 _cell_volume 3171.4(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 6463 _cell_measurement_theta_min 2.9344 _cell_measurement_theta_max 32.6742 _exptl_absorpt_correction_T_min 0.94214 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.2890 _diffrn_reflns_number 46490 _diffrn_reflns_av_R_equivalents 0.0651 _diffrn_reflns_av_sigmaI/netI 0.2005 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.9344 _diffrn_reflns_theta_max 32.6742 _diffrn_orient_matrix_UB_11 -0.0488832932 _diffrn_orient_matrix_UB_12 -0.0055937133 _diffrn_orient_matrix_UB_13 -0.0106614210 _diffrn_orient_matrix_UB_21 -0.0147870910 _diffrn_orient_matrix_UB_22 0.0278422800 _diffrn_orient_matrix_UB_23 0.0227618285 _diffrn_orient_matrix_UB_31 0.0017647723 _diffrn_orient_matrix_UB_32 0.0786088566 _diffrn_orient_matrix_UB_33 -0.0088349636 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -14.00 44.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.5247 77.0000 0.0000 0.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 2 omega -14.00 98.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.5247 77.0000 240.0000 0.0000 0.0000 112 #__ type_ start__ end____ width___ exp.time_ 3 omega 40.00 98.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.5247 77.0000 90.0000 0.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 4 omega -54.00 3.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -19.9935 77.0000 120.0000 0.0000 0.0000 57 #__ type_ start__ end____ width___ exp.time_ 5 omega 1.00 59.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -19.9935 77.0000 330.0000 0.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 6 omega -36.00 5.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -19.9935 77.0000 0.0000 0.0000 0.0000 41 #__ type_ start__ end____ width___ exp.time_ 7 omega -39.00 3.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -19.9935 77.0000 60.0000 0.0000 0.0000 42 #__ type_ start__ end____ width___ exp.time_ 8 omega 4.00 57.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -19.9935 77.0000 90.0000 0.0000 0.0000 53 ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N O2' _chemical_formula_weight 281.34 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.077 _exptl_special_details ; ; _reflns_number_total 10847 _reflns_number_gt 2749 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0200P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10847 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2104 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.0848 _refine_ls_wR_factor_gt 0.0773 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _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 N1 N 0.91495(8) 1.03144(15) 0.41173(5) 0.0791(4) Uani 1 1 d . . . O1 O 0.85309(7) 0.78053(12) 0.41485(5) 0.1014(4) Uani 1 1 d . . . O2 O 1.07007(7) 0.88479(11) 0.36968(4) 0.0826(3) Uani 1 1 d . . . C1 C 0.92068(11) 0.88470(19) 0.40457(6) 0.0754(5) Uani 1 1 d . . . C2 C 0.88321(14) 0.62152(19) 0.40217(8) 0.0971(6) Uani 1 1 d . . . C3 C 0.88947(15) 0.5244(2) 0.44999(8) 0.1464(8) Uani 1 1 d . . . H3A H 0.9371 0.5691 0.4748 0.220 Uiso 1 1 calc R . . H3B H 0.9072 0.4183 0.4430 0.220 Uiso 1 1 calc R . . H3C H 0.8281 0.5245 0.4624 0.220 Uiso 1 1 calc R . . C4 C 0.80944(13) 0.5582(2) 0.36122(8) 0.1336(8) Uani 1 1 d . . . H4A H 0.8093 0.6217 0.3317 0.200 Uiso 1 1 calc R . . H4B H 0.7468 0.5612 0.3723 0.200 Uiso 1 1 calc R . . H4C H 0.8253 0.4516 0.3537 0.200 Uiso 1 1 calc R . . C5 C 0.97822(12) 0.64943(19) 0.38457(6) 0.0923(6) Uani 1 1 d . . . H5A H 1.0184 0.5708 0.3749 0.111 Uiso 1 1 calc R . . C6 C 0.99749(11) 0.80007(18) 0.38449(6) 0.0717(5) Uani 1 1 d . . . C7 C 1.14057(11) 0.79082(19) 0.34841(6) 0.0920(5) Uani 1 1 d . . . H7A H 1.1087 0.7187 0.3237 0.110 Uiso 1 1 calc R . . H7B H 1.1776 0.7296 0.3745 0.110 Uiso 1 1 calc R . . C8 C 1.20443(12) 0.8960(2) 0.32468(8) 0.1260(7) Uani 1 1 d . . . H8A H 1.2511 0.8347 0.3098 0.189 Uiso 1 1 calc R . . H8B H 1.2369 0.9652 0.3495 0.189 Uiso 1 1 calc R . . H8C H 1.1672 0.9570 0.2992 0.189 Uiso 1 1 calc R . . C9 C 0.83498(11) 1.09473(16) 0.43461(8) 0.0692(4) Uani 1 1 d . . . C10 C 0.83899(13) 1.1075(2) 0.48477(8) 0.0910(5) Uani 1 1 d . . . H10A H 0.8912 1.0655 0.5052 0.109 Uiso 1 1 calc R . . C11 C 0.76572(18) 1.1832(3) 0.50650(7) 0.1057(6) Uani 1 1 d . . . H11A H 0.7694 1.1893 0.5412 0.127 Uiso 1 1 calc R . . C12 C 0.68877(14) 1.2482(2) 0.47734(9) 0.0917(6) Uani 1 1 d . . . H12A H 0.6412 1.3007 0.4920 0.110 Uiso 1 1 calc R . . C13 C 0.68244(11) 1.23474(17) 0.42463(8) 0.0652(4) Uani 1 1 d . . . C14 C 0.75605(10) 1.15459(15) 0.40323(6) 0.0564(4) Uani 1 1 d . . . C15 C 0.74713(12) 1.14025(16) 0.34992(7) 0.0716(4) Uani 1 1 d . . . H15A H 0.7939 1.0871 0.3348 0.086 Uiso 1 1 calc R . . C16 C 0.66954(15) 1.2050(2) 0.32125(7) 0.0880(5) Uani 1 1 d . . . H16A H 0.6635 1.1942 0.2866 0.106 Uiso 1 1 calc R . . C17 C 0.60011(14) 1.2860(2) 0.34294(10) 0.0974(6) Uani 1 1 d . . . H17A H 0.5487 1.3316 0.3228 0.117 Uiso 1 1 calc R . . C18 C 0.60631(12) 1.29935(19) 0.39275(9) 0.0857(5) Uani 1 1 d . . . H18A H 0.5583 1.3535 0.4066 0.103 Uiso 1 1 calc R . . N1' N 0.63094(8) 0.01728(13) 0.16128(4) 0.0541(3) Uani 1 1 d . . . O1' O 0.57676(6) 0.19108(10) 0.09584(3) 0.0642(3) Uani 1 1 d . . . C1' C 0.57662(9) 0.12530(16) 0.14203(5) 0.0517(3) Uani 1 1 d . . . C2' C 0.50311(10) 0.31643(17) 0.08822(6) 0.0672(4) Uani 1 1 d . . . C3' C 0.55473(11) 0.46829(17) 0.07848(6) 0.0883(5) Uani 1 1 d . . . H3'A H 0.5991 0.4948 0.1074 0.133 Uiso 1 1 calc R . . H3'B H 0.5085 0.5514 0.0718 0.133 Uiso 1 1 calc R . . H3'C H 0.5893 0.4548 0.0501 0.133 Uiso 1 1 calc R . . C4' C 0.43083(11) 0.26715(19) 0.04397(6) 0.0958(6) Uani 1 1 d . . . H4'A H 0.4001 0.1710 0.0519 0.144 Uiso 1 1 calc R . . H4'B H 0.4636 0.2513 0.0150 0.144 Uiso 1 1 calc R . . H4'C H 0.3832 0.3481 0.0370 0.144 Uiso 1 1 calc R . . O2' O 0.48722(6) 0.15487(11) 0.21216(4) 0.0668(3) Uani 1 1 d . . . C5' C 0.46082(9) 0.31643(17) 0.13621(6) 0.0653(4) Uani 1 1 d . . . H5'A H 0.4128 0.3844 0.1440 0.078 Uiso 1 1 calc R . . C6' C 0.50173(9) 0.20509(17) 0.16635(6) 0.0555(4) Uani 1 1 d . . . C7' C 0.40762(10) 0.22697(18) 0.23276(5) 0.0738(4) Uani 1 1 d . . . H7'A H 0.3532 0.2392 0.2070 0.089 Uiso 1 1 calc R . . H7'B H 0.4259 0.3300 0.2463 0.089 Uiso 1 1 calc R . . C8' C 0.38199(11) 0.12053(18) 0.27336(6) 0.0915(5) Uani 1 1 d . . . H8'A H 0.3293 0.1650 0.2883 0.137 Uiso 1 1 calc R . . H8'B H 0.4366 0.1089 0.2985 0.137 Uiso 1 1 calc R . . H8'C H 0.3637 0.0193 0.2594 0.137 Uiso 1 1 calc R . . C9' C 0.70055(9) -0.05926(14) 0.13621(6) 0.0507(4) Uani 1 1 d . . . C10' C 0.68702(10) -0.10215(16) 0.08654(6) 0.0661(4) Uani 1 1 d . . . H10B H 0.6306 -0.0732 0.0667 0.079 Uiso 1 1 calc R . . C11' C 0.75697(12) -0.18886(17) 0.06525(6) 0.0762(5) Uani 1 1 d . . . H11B H 0.7457 -0.2181 0.0317 0.091 Uiso 1 1 calc R . . C12' C 0.84048(11) -0.23059(16) 0.09287(7) 0.0702(4) Uani 1 1 d . . . H12B H 0.8863 -0.2872 0.0780 0.084 Uiso 1 1 calc R . . C13' C 0.85853(10) -0.18915(15) 0.14364(6) 0.0584(4) Uani 1 1 d . . . C14' C 0.78819(9) -0.10387(14) 0.16602(6) 0.0501(3) Uani 1 1 d . . . C15' C 0.80765(11) -0.06491(16) 0.21700(6) 0.0680(4) Uani 1 1 d . . . H15B H 0.7620 -0.0100 0.2325 0.082 Uiso 1 1 calc R . . C16' C 0.89261(13) -0.1064(2) 0.24421(6) 0.0913(5) Uani 1 1 d . . . H16B H 0.9048 -0.0784 0.2779 0.110 Uiso 1 1 calc R . . C17' C 0.96144(12) -0.1907(2) 0.22175(8) 0.1011(6) Uani 1 1 d . . . H17B H 1.0191 -0.2188 0.2407 0.121 Uiso 1 1 calc R . . C18' C 0.94540(11) -0.23174(17) 0.17312(8) 0.0788(5) Uani 1 1 d . . . H18B H 0.9918 -0.2885 0.1588 0.095 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0621(8) 0.0498(8) 0.1286(12) 0.0051(8) 0.0248(8) 0.0007(7) O1 0.0788(8) 0.0495(7) 0.1790(12) 0.0041(7) 0.0285(7) -0.0151(6) O2 0.0580(6) 0.0596(6) 0.1325(10) -0.0089(7) 0.0209(6) 0.0069(6) C1 0.0587(10) 0.0465(10) 0.1192(14) 0.0094(10) 0.0041(10) -0.0049(9) C2 0.0942(15) 0.0477(11) 0.1450(18) 0.0030(12) -0.0026(13) -0.0081(10) C3 0.185(2) 0.0804(14) 0.172(2) 0.0304(15) 0.0161(17) -0.0166(14) C4 0.1076(15) 0.0937(14) 0.190(2) -0.0035(14) -0.0184(15) -0.0353(12) C5 0.0810(13) 0.0487(11) 0.1418(17) -0.0085(11) -0.0077(12) 0.0085(9) C6 0.0554(10) 0.0482(10) 0.1094(14) -0.0050(10) 0.0026(9) 0.0052(9) C7 0.0725(11) 0.0900(13) 0.1111(15) -0.0163(11) 0.0017(10) 0.0297(11) C8 0.0771(12) 0.1168(16) 0.193(2) -0.0194(15) 0.0541(14) 0.0058(12) C9 0.0667(12) 0.0508(10) 0.0915(14) 0.0072(10) 0.0150(11) -0.0129(8) C10 0.0919(14) 0.0973(14) 0.0832(16) 0.0216(12) 0.0081(12) -0.0024(11) C11 0.1276(18) 0.1312(18) 0.0631(14) 0.0009(13) 0.0307(14) -0.0278(15) C12 0.0916(15) 0.0895(13) 0.1027(17) -0.0134(12) 0.0474(13) -0.0135(11) C13 0.0538(11) 0.0516(9) 0.0936(14) 0.0024(9) 0.0230(11) -0.0059(8) C14 0.0516(10) 0.0416(8) 0.0767(13) 0.0024(8) 0.0111(9) -0.0085(7) C15 0.0765(12) 0.0495(9) 0.0923(14) -0.0121(10) 0.0251(10) -0.0091(8) C16 0.1004(14) 0.0748(12) 0.0838(14) -0.0047(11) -0.0080(13) -0.0114(11) C17 0.0772(14) 0.0688(13) 0.140(2) 0.0031(14) -0.0103(14) -0.0077(10) C18 0.0623(12) 0.0642(11) 0.1320(17) 0.0000(13) 0.0174(13) -0.0030(9) N1' 0.0496(7) 0.0533(7) 0.0597(8) 0.0064(6) 0.0080(6) 0.0070(6) O1' 0.0771(7) 0.0617(6) 0.0559(7) 0.0096(5) 0.0163(5) 0.0210(5) C1' 0.0515(9) 0.0524(9) 0.0515(10) 0.0015(8) 0.0071(7) -0.0001(8) C2' 0.0755(11) 0.0639(11) 0.0621(11) 0.0089(9) 0.0085(9) 0.0248(9) C3' 0.1116(13) 0.0675(11) 0.0896(13) 0.0192(10) 0.0272(10) 0.0224(10) C4' 0.1039(13) 0.1087(14) 0.0692(12) 0.0022(10) -0.0112(10) 0.0265(11) O2' 0.0609(6) 0.0826(7) 0.0591(7) 0.0049(6) 0.0169(5) 0.0163(5) C5' 0.0609(10) 0.0709(10) 0.0637(11) -0.0027(9) 0.0061(8) 0.0180(8) C6' 0.0518(9) 0.0638(10) 0.0517(10) 0.0003(8) 0.0092(8) 0.0056(8) C7' 0.0655(10) 0.0892(11) 0.0684(11) -0.0060(9) 0.0155(9) 0.0142(9) C8' 0.0957(12) 0.0902(12) 0.0980(14) -0.0023(11) 0.0493(10) -0.0007(10) C9' 0.0520(9) 0.0412(8) 0.0598(11) 0.0054(8) 0.0110(8) -0.0003(7) C10' 0.0608(10) 0.0710(10) 0.0650(12) -0.0019(9) 0.0024(9) 0.0087(8) C11' 0.0851(12) 0.0793(11) 0.0647(11) -0.0133(9) 0.0111(10) 0.0110(10) C12' 0.0650(11) 0.0627(10) 0.0854(13) -0.0049(10) 0.0196(10) 0.0112(8) C13' 0.0547(10) 0.0466(9) 0.0738(12) 0.0033(9) 0.0083(9) 0.0008(8) C14' 0.0501(9) 0.0381(8) 0.0625(11) 0.0076(8) 0.0085(8) -0.0006(7) C15' 0.0699(11) 0.0663(10) 0.0666(12) 0.0029(9) 0.0043(9) 0.0070(8) C16' 0.0877(13) 0.1036(14) 0.0762(13) -0.0027(11) -0.0155(12) 0.0173(11) C17' 0.0761(13) 0.1108(15) 0.1087(18) 0.0001(13) -0.0195(13) 0.0268(11) C18' 0.0588(11) 0.0712(11) 0.1050(15) -0.0001(11) 0.0040(11) 0.0169(8) _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 N1 C1 1.2654(16) . ? N1 C9 1.4460(18) . ? O1 C1 1.3490(16) . ? O1 C2 1.4678(18) . ? O2 C6 1.3452(16) . ? O2 C7 1.4415(15) . ? C1 C6 1.4520(19) . ? C2 C5 1.485(2) . ? C2 C4 1.512(2) . ? C2 C3 1.520(2) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.3079(18) . ? C5 H5A 0.9300 . ? C7 C8 1.465(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.346(2) . ? C9 C14 1.3999(18) . ? C10 C11 1.398(2) . ? C10 H10A 0.9300 . ? C11 C12 1.368(2) . ? C11 H11A 0.9300 . ? C12 C13 1.413(2) . ? C12 H12A 0.9300 . ? C13 C18 1.395(2) . ? C13 C14 1.4155(19) . ? C14 C15 1.4275(18) . ? C15 C16 1.367(2) . ? C15 H15A 0.9300 . ? C16 C17 1.378(2) . ? C16 H16A 0.9300 . ? C17 C18 1.335(2) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? N1' C1' 1.2611(15) . ? N1' C9' 1.4105(15) . ? O1' C1' 1.3615(14) . ? O1' C2' 1.4788(14) . ? C1' C6' 1.4683(17) . ? C2' C5' 1.4840(17) . ? C2' C3' 1.5173(18) . ? C2' C4' 1.5216(18) . ? C3' H3'A 0.9600 . ? C3' H3'B 0.9600 . ? C3' H3'C 0.9600 . ? C4' H4'A 0.9600 . ? C4' H4'B 0.9600 . ? C4' H4'C 0.9600 . ? O2' C6' 1.3418(15) . ? O2' C7' 1.4410(14) . ? C5' C6' 1.3281(16) . ? C5' H5'A 0.9300 . ? C7' C8' 1.4944(17) . ? C7' H7'A 0.9700 . ? C7' H7'B 0.9700 . ? C8' H8'A 0.9600 . ? C8' H8'B 0.9600 . ? C8' H8'C 0.9600 . ? C9' C10' 1.3737(17) . ? C9' C14' 1.4309(16) . ? C10' C11' 1.4027(18) . ? C10' H10B 0.9300 . ? C11' C12' 1.3522(18) . ? C11' H11B 0.9300 . ? C12' C13' 1.4012(18) . ? C12' H12B 0.9300 . ? C13' C18' 1.4140(18) . ? C13' C14' 1.4153(17) . ? C14' C15' 1.4028(17) . ? C15' C16' 1.3630(18) . ? C15' H15B 0.9300 . ? C16' C17' 1.396(2) . ? C16' H16B 0.9300 . ? C17' C18' 1.344(2) . ? C17' H17B 0.9300 . ? C18' H18B 0.9300 . ? 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 119.87(13) . . ? C1 O1 C2 109.10(13) . . ? C6 O2 C7 113.61(12) . . ? N1 C1 O1 123.77(15) . . ? N1 C1 C6 127.46(15) . . ? O1 C1 C6 108.78(13) . . ? O1 C2 C5 102.80(12) . . ? O1 C2 C4 107.84(14) . . ? C5 C2 C4 112.54(17) . . ? O1 C2 C3 106.93(16) . . ? C5 C2 C3 113.31(16) . . ? C4 C2 C3 112.63(15) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C2 110.48(14) . . ? C6 C5 H5A 124.8 . . ? C2 C5 H5A 124.8 . . ? C5 C6 O2 133.43(15) . . ? C5 C6 C1 108.76(15) . . ? O2 C6 C1 117.81(13) . . ? O2 C7 C8 108.64(13) . . ? O2 C7 H7A 110.0 . . ? C8 C7 H7A 110.0 . . ? O2 C7 H7B 110.0 . . ? C8 C7 H7B 110.0 . . ? H7A C7 H7B 108.3 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 120.36(16) . . ? C10 C9 N1 121.14(17) . . ? C14 C9 N1 118.30(17) . . ? C9 C10 C11 120.89(18) . . ? C9 C10 H10A 119.6 . . ? C11 C10 H10A 119.6 . . ? C12 C11 C10 120.87(18) . . ? C12 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C11 C12 C13 119.25(17) . . ? C11 C12 H12A 120.4 . . ? C13 C12 H12A 120.4 . . ? C18 C13 C12 122.16(18) . . ? C18 C13 C14 118.64(17) . . ? C12 C13 C14 119.21(16) . . ? C9 C14 C13 119.36(16) . . ? C9 C14 C15 122.53(16) . . ? C13 C14 C15 118.11(15) . . ? C16 C15 C14 119.72(15) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C15 C16 C17 121.04(18) . . ? C15 C16 H16A 119.5 . . ? C17 C16 H16A 119.5 . . ? C18 C17 C16 120.30(19) . . ? C18 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? C17 C18 C13 122.16(18) . . ? C17 C18 H18A 118.9 . . ? C13 C18 H18A 118.9 . . ? C1' N1' C9' 123.84(12) . . ? C1' O1' C2' 109.99(10) . . ? N1' C1' O1' 127.13(12) . . ? N1' C1' C6' 125.52(14) . . ? O1' C1' C6' 107.34(12) . . ? O1' C2' C5' 103.08(11) . . ? O1' C2' C3' 107.29(11) . . ? C5' C2' C3' 113.57(13) . . ? O1' C2' C4' 107.15(11) . . ? C5' C2' C4' 112.38(13) . . ? C3' C2' C4' 112.58(13) . . ? C2' C3' H3'A 109.5 . . ? C2' C3' H3'B 109.5 . . ? H3'A C3' H3'B 109.5 . . ? C2' C3' H3'C 109.5 . . ? H3'A C3' H3'C 109.5 . . ? H3'B C3' H3'C 109.5 . . ? C2' C4' H4'A 109.5 . . ? C2' C4' H4'B 109.5 . . ? H4'A C4' H4'B 109.5 . . ? C2' C4' H4'C 109.5 . . ? H4'A C4' H4'C 109.5 . . ? H4'B C4' H4'C 109.5 . . ? C6' O2' C7' 115.43(11) . . ? C6' C5' C2' 109.97(13) . . ? C6' C5' H5'A 125.0 . . ? C2' C5' H5'A 125.0 . . ? C5' C6' O2' 133.08(13) . . ? C5' C6' C1' 109.58(14) . . ? O2' C6' C1' 117.33(13) . . ? O2' C7' C8' 106.87(12) . . ? O2' C7' H7'A 110.3 . . ? C8' C7' H7'A 110.3 . . ? O2' C7' H7'B 110.3 . . ? C8' C7' H7'B 110.3 . . ? H7'A C7' H7'B 108.6 . . ? C7' C8' H8'A 109.5 . . ? C7' C8' H8'B 109.5 . . ? H8'A C8' H8'B 109.5 . . ? C7' C8' H8'C 109.5 . . ? H8'A C8' H8'C 109.5 . . ? H8'B C8' H8'C 109.5 . . ? C10' C9' N1' 124.48(12) . . ? C10' C9' C14' 118.63(13) . . ? N1' C9' C14' 116.75(13) . . ? C9' C10' C11' 121.08(14) . . ? C9' C10' H10B 119.5 . . ? C11' C10' H10B 119.5 . . ? C12' C11' C10' 120.92(15) . . ? C12' C11' H11B 119.5 . . ? C10' C11' H11B 119.5 . . ? C11' C12' C13' 120.52(14) . . ? C11' C12' H12B 119.7 . . ? C13' C12' H12B 119.7 . . ? C12' C13' C18' 121.33(15) . . ? C12' C13' C14' 119.43(14) . . ? C18' C13' C14' 119.24(15) . . ? C15' C14' C13' 118.33(13) . . ? C15' C14' C9' 122.25(13) . . ? C13' C14' C9' 119.42(14) . . ? C16' C15' C14' 120.92(14) . . ? C16' C15' H15B 119.5 . . ? C14' C15' H15B 119.5 . . ? C15' C16' C17' 120.26(16) . . ? C15' C16' H16B 119.9 . . ? C17' C16' H16B 119.9 . . ? C18' C17' C16' 120.80(16) . . ? C18' C17' H17B 119.6 . . ? C16' C17' H17B 119.6 . . ? C17' C18' C13' 120.44(15) . . ? C17' C18' H18B 119.8 . . ? C13' C18' H18B 119.8 . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 32.73 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.315 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.026