# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2a-S,S,S _database_code_depnum_ccdc_archive 'CCDC 903368' #TrackingRef 'XRD_Structures_5_compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 N O' _chemical_formula_sum 'C15 H17 N O' _chemical_formula_weight 227.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(1) _space_group_name_Hall 'P 61' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/6' 'y, -x+y, z+5/6' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' _cell_length_a 7.3117(2) _cell_length_b 7.3117(2) _cell_length_c 37.2526(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1724.74(8) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9951 _cell_measurement_theta_min 6.99 _cell_measurement_theta_max 65.84 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.639 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6592 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14783 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 6.99 _diffrn_reflns_theta_max 66.16 _reflns_number_total 1958 _reflns_number_gt 1949 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.4039P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(3) _chemical_absolute_configuration ad _refine_ls_number_reflns 1958 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0773 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.06394(18) 1.25066(17) 0.10199(3) 0.0258(3) Uani 1 1 d . . . N1 N -0.08320(19) 0.9470(2) 0.13436(3) 0.0195(3) Uani 1 1 d . . . C1 C 0.4705(2) 1.0884(3) 0.19031(4) 0.0245(3) Uani 1 1 d . . . H1 H 0.5959 1.1183 0.2028 0.029 Uiso 1 1 calc R . . C2 C 0.3771(2) 0.9183(3) 0.16681(5) 0.0231(3) Uani 1 1 d . . . H2 H 0.4371 0.8305 0.1635 0.028 Uiso 1 1 calc R . . C3 C 0.1954(2) 0.8768(3) 0.14811(4) 0.0205(3) Uani 1 1 d . . . C4 C 0.1080(2) 1.0064(2) 0.15380(4) 0.0197(3) Uani 1 1 d . . . C5 C -0.2442(2) 0.7226(2) 0.13832(4) 0.0199(3) Uani 1 1 d . . . H5 H -0.3268 0.6964 0.1610 0.024 Uiso 1 1 calc R . . C6 C -0.3916(2) 0.6133(2) 0.10551(4) 0.0221(3) Uani 1 1 d . . . H6 H -0.5440 0.5520 0.1119 0.026 Uiso 1 1 calc R . . C7 C -0.3328(3) 0.7529(3) 0.07264(4) 0.0246(4) Uani 1 1 d . . . H7A H -0.4519 0.6940 0.0554 0.029 Uiso 1 1 calc R . . H7B H -0.2090 0.7590 0.0607 0.029 Uiso 1 1 calc R . . C8 C 0.3807(2) 1.2144(2) 0.19561(4) 0.0237(3) Uani 1 1 d . . . H8 H 0.4470 1.3312 0.2115 0.028 Uiso 1 1 calc R . . C9 C 0.1952(2) 1.1740(2) 0.17809(4) 0.0217(3) Uani 1 1 d . . . C10 C 0.0931(3) 1.3033(3) 0.18672(4) 0.0256(4) Uani 1 1 d . . . H10A H 0.1885 1.4508 0.1800 0.038 Uiso 1 1 calc R . . H10B H 0.0637 1.2950 0.2125 0.038 Uiso 1 1 calc R . . H10C H -0.0393 1.2485 0.1733 0.038 Uiso 1 1 calc R . . C11 C -0.0847(2) 1.0729(2) 0.10738(4) 0.0208(3) Uani 1 1 d . . . C12 C -0.2804(3) 0.9756(3) 0.08402(4) 0.0238(3) Uani 1 1 d . . . H12A H -0.2558 1.0643 0.0625 0.029 Uiso 1 1 calc R . . H12B H -0.4006 0.9682 0.0975 0.029 Uiso 1 1 calc R . . C13 C -0.1527(2) 0.5721(2) 0.13484(4) 0.0214(3) Uani 1 1 d . . . H13 H -0.1718 0.4891 0.1572 0.026 Uiso 1 1 calc R . . C14 C -0.3225(2) 0.4437(2) 0.10611(4) 0.0238(3) Uani 1 1 d . . . H14A H -0.4342 0.3038 0.1147 0.029 Uiso 1 1 calc R . . H14B H -0.2628 0.4305 0.0830 0.029 Uiso 1 1 calc R . . C15 C 0.0778(2) 0.6948(2) 0.12271(4) 0.0229(3) Uani 1 1 d . . . H15A H 0.1401 0.6018 0.1230 0.027 Uiso 1 1 calc R . . H15B H 0.0869 0.7477 0.0979 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0306(6) 0.0205(6) 0.0249(6) 0.0010(4) -0.0012(5) 0.0117(5) N1 0.0207(6) 0.0196(6) 0.0196(7) -0.0017(5) -0.0024(5) 0.0111(5) C1 0.0186(7) 0.0275(8) 0.0229(8) 0.0047(6) -0.0008(6) 0.0080(6) C2 0.0212(7) 0.0247(8) 0.0251(8) 0.0055(6) 0.0045(6) 0.0129(6) C3 0.0213(8) 0.0210(8) 0.0192(8) 0.0054(6) 0.0045(6) 0.0106(6) C4 0.0209(7) 0.0211(8) 0.0171(7) 0.0039(6) 0.0012(6) 0.0105(6) C5 0.0202(7) 0.0207(8) 0.0188(7) -0.0001(6) 0.0010(6) 0.0103(6) C6 0.0185(7) 0.0221(7) 0.0244(8) -0.0043(7) -0.0033(6) 0.0093(6) C7 0.0279(8) 0.0266(8) 0.0220(8) -0.0043(6) -0.0053(6) 0.0157(7) C8 0.0223(8) 0.0206(7) 0.0209(9) -0.0007(6) -0.0007(6) 0.0054(6) C9 0.0237(8) 0.0211(8) 0.0183(8) 0.0040(6) 0.0020(6) 0.0096(6) C10 0.0317(8) 0.0240(8) 0.0222(8) -0.0035(6) -0.0033(7) 0.0147(7) C11 0.0271(8) 0.0207(7) 0.0194(8) -0.0025(6) 0.0000(6) 0.0155(7) C12 0.0270(8) 0.0265(8) 0.0207(8) -0.0008(6) -0.0039(6) 0.0156(7) C13 0.0248(8) 0.0198(7) 0.0213(8) 0.0009(6) 0.0001(6) 0.0126(6) C14 0.0255(8) 0.0205(8) 0.0245(8) -0.0014(6) -0.0013(6) 0.0108(7) C15 0.0252(8) 0.0240(8) 0.0229(8) 0.0000(6) 0.0026(6) 0.0148(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.224(2) . ? N1 C11 1.367(2) . ? N1 C4 1.4355(19) . ? N1 C5 1.4725(19) . ? C1 C8 1.387(2) . ? C1 C2 1.389(2) . ? C1 H1 0.9500 . ? C2 C3 1.393(2) . ? C2 H2 0.9500 . ? C3 C4 1.399(2) . ? C3 C15 1.503(2) . ? C4 C9 1.395(2) . ? C5 C13 1.553(2) . ? C5 C6 1.560(2) . ? C5 H5 1.0000 . ? C6 C7 1.512(2) . ? C6 C14 1.556(2) . ? C6 H6 1.0000 . ? C7 C12 1.534(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.397(2) . ? C8 H8 0.9500 . ? C9 C10 1.504(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.514(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C15 1.529(2) . ? C13 C14 1.550(2) . ? C13 H13 1.0000 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? 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 C11 N1 C4 120.13(12) . . ? C11 N1 C5 123.57(12) . . ? C4 N1 C5 113.69(12) . . ? C8 C1 C2 119.99(15) . . ? C8 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C1 C2 C3 119.94(15) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 119.04(15) . . ? C2 C3 C15 124.68(14) . . ? C4 C3 C15 116.24(13) . . ? C9 C4 C3 122.06(14) . . ? C9 C4 N1 122.76(14) . . ? C3 C4 N1 115.10(14) . . ? N1 C5 C13 113.16(12) . . ? N1 C5 C6 117.08(13) . . ? C13 C5 C6 90.22(12) . . ? N1 C5 H5 111.6 . . ? C13 C5 H5 111.6 . . ? C6 C5 H5 111.6 . . ? C7 C6 C14 116.98(13) . . ? C7 C6 C5 113.47(12) . . ? C14 C6 C5 88.89(12) . . ? C7 C6 H6 111.9 . . ? C14 C6 H6 111.9 . . ? C5 C6 H6 111.9 . . ? C6 C7 C12 109.17(13) . . ? C6 C7 H7A 109.8 . . ? C12 C7 H7A 109.8 . . ? C6 C7 H7B 109.8 . . ? C12 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? C1 C8 C9 121.66(15) . . ? C1 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C4 C9 C8 117.25(14) . . ? C4 C9 C10 122.62(14) . . ? C8 C9 C10 120.10(14) . . ? 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 . . ? O1 C11 N1 122.26(14) . . ? O1 C11 C12 122.26(14) . . ? N1 C11 C12 115.46(13) . . ? C11 C12 C7 109.49(12) . . ? C11 C12 H12A 109.8 . . ? C7 C12 H12A 109.8 . . ? C11 C12 H12B 109.8 . . ? C7 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? C15 C13 C14 117.73(13) . . ? C15 C13 C5 110.37(12) . . ? C14 C13 C5 89.33(12) . . ? C15 C13 H13 112.4 . . ? C14 C13 H13 112.4 . . ? C5 C13 H13 112.4 . . ? C13 C14 C6 90.46(11) . . ? C13 C14 H14A 113.6 . . ? C6 C14 H14A 113.6 . . ? C13 C14 H14B 113.6 . . ? C6 C14 H14B 113.6 . . ? H14A C14 H14B 110.8 . . ? C3 C15 C13 107.93(12) . . ? C3 C15 H15A 110.1 . . ? C13 C15 H15A 110.1 . . ? C3 C15 H15B 110.1 . . ? C13 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 66.16 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.147 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.031 data_2a-R,R,R _database_code_depnum_ccdc_archive 'CCDC 903369' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 N O' _chemical_formula_sum 'C15 H17 N O' _chemical_formula_weight 227.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(5) _space_group_name_Hall 'P 65' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+5/6' 'y, -x+y, z+1/6' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' _cell_length_a 7.3171(2) _cell_length_b 7.3171(2) _cell_length_c 37.2390(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1726.66(8) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8724 _cell_measurement_theta_min 6.99 _cell_measurement_theta_max 65.75 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.638 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6760 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13311 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 6.99 _diffrn_reflns_theta_max 66.21 _reflns_number_total 1966 _reflns_number_gt 1930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.2855P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 1966 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.06383(17) -0.18708(17) 0.09357(3) 0.0247(3) Uani 1 1 d . . . C1 C 1.4704(2) 0.3817(3) 0.18183(4) 0.0233(3) Uani 1 1 d . . . H1 H 1.5959 0.4770 0.1942 0.028 Uiso 1 1 calc R . . C2 C 1.3768(2) 0.4583(2) 0.15833(4) 0.0222(3) Uani 1 1 d . . . H2 H 1.4367 0.6060 0.1550 0.027 Uiso 1 1 calc R . . C3 C 1.1948(2) 0.3182(2) 0.13960(4) 0.0189(3) Uani 1 1 d . . . C4 C 1.0776(2) 0.3827(2) 0.11424(4) 0.0212(3) Uani 1 1 d . . . H4A H 1.0869 0.3392 0.0894 0.025 Uiso 1 1 calc R . . H4B H 1.1397 0.5379 0.1146 0.025 Uiso 1 1 calc R . . C5 C 0.8471(2) 0.2746(2) 0.12633(4) 0.0201(3) Uani 1 1 d . . . H5 H 0.8278 0.3385 0.1487 0.024 Uiso 1 1 calc R . . C6 C 0.6776(2) 0.2333(3) 0.09760(4) 0.0226(3) Uani 1 1 d . . . H6A H 0.7372 0.3060 0.0745 0.027 Uiso 1 1 calc R . . H6B H 0.5660 0.2617 0.1062 0.027 Uiso 1 1 calc R . . C7 C 0.6084(2) -0.0052(2) 0.09704(4) 0.0210(3) Uani 1 1 d . . . H7 H 0.4561 -0.0962 0.1035 0.025 Uiso 1 1 calc R . . C8 C 0.6670(3) -0.0860(2) 0.06423(4) 0.0230(3) Uani 1 1 d . . . H8A H 0.7907 0.0317 0.0523 0.028 Uiso 1 1 calc R . . H8B H 0.5480 -0.1462 0.0470 0.028 Uiso 1 1 calc R . . C9 C 1.3804(2) 0.1662(3) 0.18714(4) 0.0225(3) Uani 1 1 d . . . H9 H 1.4466 0.1159 0.2031 0.027 Uiso 1 1 calc R . . C10 C 1.1948(2) 0.0207(2) 0.16964(4) 0.0204(3) Uani 1 1 d . . . C11 C 1.1080(2) 0.1017(2) 0.14534(4) 0.0183(3) Uani 1 1 d . . . C12 C 0.7561(2) 0.0330(2) 0.12985(4) 0.0188(3) Uani 1 1 d . . . H12 H 0.6737 -0.0232 0.1526 0.023 Uiso 1 1 calc R . . C13 C 0.7195(2) -0.2560(2) 0.07560(4) 0.0228(3) Uani 1 1 d . . . H13A H 0.5996 -0.3685 0.0892 0.027 Uiso 1 1 calc R . . H13B H 0.7435 -0.3204 0.0540 0.027 Uiso 1 1 calc R . . C14 C 0.9154(2) -0.1579(2) 0.09883(4) 0.0195(3) Uani 1 1 d . . . N1 N 0.91659(18) -0.0303(2) 0.12591(3) 0.0180(3) Uani 1 1 d . . . C16 C 1.0929(3) -0.2101(2) 0.17822(4) 0.0249(4) Uani 1 1 d . . . H16A H 0.9589 -0.2871 0.1652 0.037 Uiso 1 1 calc R . . H16B H 1.0664 -0.2310 0.2041 0.037 Uiso 1 1 calc R . . H16C H 1.1867 -0.2630 0.1709 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0286(6) 0.0261(6) 0.0255(6) -0.0027(4) -0.0007(5) 0.0182(5) C1 0.0166(7) 0.0282(8) 0.0228(8) -0.0062(7) -0.0005(6) 0.0095(6) C2 0.0198(8) 0.0182(7) 0.0252(8) -0.0010(6) 0.0053(6) 0.0070(6) C3 0.0189(8) 0.0188(8) 0.0183(8) -0.0013(6) 0.0040(6) 0.0088(6) C4 0.0244(8) 0.0168(7) 0.0220(8) 0.0033(6) 0.0037(6) 0.0100(7) C5 0.0234(8) 0.0167(7) 0.0211(7) -0.0013(6) 0.0000(6) 0.0107(6) C6 0.0240(8) 0.0225(8) 0.0240(8) 0.0003(6) -0.0007(7) 0.0136(7) C7 0.0174(7) 0.0206(8) 0.0240(8) 0.0009(6) -0.0020(6) 0.0087(6) C8 0.0253(8) 0.0217(8) 0.0215(8) -0.0015(6) -0.0047(6) 0.0113(7) C9 0.0208(8) 0.0300(9) 0.0210(8) -0.0009(6) -0.0006(6) 0.0160(7) C10 0.0218(8) 0.0242(8) 0.0180(7) -0.0018(6) 0.0026(6) 0.0137(7) C11 0.0185(7) 0.0190(8) 0.0171(7) -0.0035(6) 0.0007(6) 0.0092(6) C12 0.0186(7) 0.0176(7) 0.0191(7) 0.0003(6) 0.0019(6) 0.0082(6) C13 0.0248(8) 0.0200(8) 0.0217(8) -0.0035(6) -0.0036(6) 0.0098(7) C14 0.0264(8) 0.0149(7) 0.0186(7) 0.0020(6) -0.0004(6) 0.0115(6) N1 0.0191(6) 0.0153(6) 0.0189(6) -0.0016(5) -0.0018(5) 0.0080(5) C16 0.0301(9) 0.0243(8) 0.0229(8) -0.0002(6) -0.0032(7) 0.0155(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.2228(19) . ? C1 C9 1.386(2) . ? C1 C2 1.390(2) . ? C1 H1 0.9500 . ? C2 C3 1.395(2) . ? C2 H2 0.9500 . ? C3 C11 1.397(2) . ? C3 C4 1.502(2) . ? C4 C5 1.529(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.549(2) . ? C5 C12 1.552(2) . ? C5 H5 1.0000 . ? C6 C7 1.555(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.510(2) . ? C7 C12 1.561(2) . ? C7 H7 1.0000 . ? C8 C13 1.534(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.399(2) . ? C9 H9 0.9500 . ? C10 C11 1.397(2) . ? C10 C16 1.501(2) . ? C11 N1 1.4369(19) . ? C12 N1 1.4697(19) . ? C12 H12 1.0000 . ? C13 C14 1.513(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N1 1.371(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 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 C9 C1 C2 119.91(15) . . ? C9 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C1 C2 C3 120.03(15) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C11 118.86(15) . . ? C2 C3 C4 124.68(14) . . ? C11 C3 C4 116.42(13) . . ? C3 C4 C5 107.93(12) . . ? C3 C4 H4A 110.1 . . ? C5 C4 H4A 110.1 . . ? C3 C4 H4B 110.1 . . ? C5 C4 H4B 110.1 . . ? H4A C4 H4B 108.4 . . ? C4 C5 C6 117.77(13) . . ? C4 C5 C12 110.35(12) . . ? C6 C5 C12 89.44(11) . . ? C4 C5 H5 112.4 . . ? C6 C5 H5 112.4 . . ? C12 C5 H5 112.4 . . ? C5 C6 C7 90.46(11) . . ? C5 C6 H6A 113.6 . . ? C7 C6 H6A 113.6 . . ? C5 C6 H6B 113.6 . . ? C7 C6 H6B 113.6 . . ? H6A C6 H6B 110.8 . . ? C8 C7 C6 116.97(13) . . ? C8 C7 C12 113.38(12) . . ? C6 C7 C12 88.89(11) . . ? C8 C7 H7 111.9 . . ? C6 C7 H7 111.9 . . ? C12 C7 H7 111.9 . . ? C7 C8 C13 109.25(12) . . ? C7 C8 H8A 109.8 . . ? C13 C8 H8A 109.8 . . ? C7 C8 H8B 109.8 . . ? C13 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? C1 C9 C10 121.86(15) . . ? C1 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C11 C10 C9 116.95(14) . . ? C11 C10 C16 122.69(14) . . ? C9 C10 C16 120.31(14) . . ? C10 C11 C3 122.32(14) . . ? C10 C11 N1 122.55(13) . . ? C3 C11 N1 115.04(13) . . ? N1 C12 C5 113.30(12) . . ? N1 C12 C7 117.14(13) . . ? C5 C12 C7 90.14(11) . . ? N1 C12 H12 111.5 . . ? C5 C12 H12 111.5 . . ? C7 C12 H12 111.5 . . ? C14 C13 C8 109.55(12) . . ? C14 C13 H13A 109.8 . . ? C8 C13 H13A 109.8 . . ? C14 C13 H13B 109.8 . . ? C8 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? O1 C14 N1 122.20(14) . . ? O1 C14 C13 122.60(14) . . ? N1 C14 C13 115.19(13) . . ? C14 N1 C11 120.01(12) . . ? C14 N1 C12 123.64(12) . . ? C11 N1 C12 113.68(12) . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 66.21 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.161 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.033 data_2c-R,R,R _database_code_depnum_ccdc_archive 'CCDC 903370' #TrackingRef 'XRD_Structures_5_compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 N O' _chemical_formula_sum 'C17 H21 N O' _chemical_formula_weight 255.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.8497(2) _cell_length_b 13.0702(3) _cell_length_c 7.9554(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.7270(10) _cell_angle_gamma 90.00 _cell_volume 685.56(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8001 _cell_measurement_theta_min 3.38 _cell_measurement_theta_max 68.12 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.589 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8248 _exptl_absorpt_correction_T_max 0.8750 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8534 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 6.70 _diffrn_reflns_theta_max 68.11 _reflns_number_total 2442 _reflns_number_gt 2426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.0791P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 2442 _refine_ls_number_parameters 175 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0785 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 O1 O 0.49264(13) 0.79716(7) 1.18440(11) 0.0279(2) Uani 1 1 d . . . N1 N 0.57626(15) 0.89907(8) 0.98264(13) 0.0220(2) Uani 1 1 d . . . C1 C 0.18968(19) 0.98679(10) 0.93470(17) 0.0280(3) Uani 1 1 d . . . H1A H 0.1325 0.9242 0.8699 0.034 Uiso 1 1 calc R . . H1B H 0.0762 1.0318 0.9425 0.034 Uiso 1 1 calc R . . C2 C 0.31984(19) 0.95897(10) 1.11798(17) 0.0281(3) Uani 1 1 d . . . H2A H 0.3919 1.0204 1.1763 0.034 Uiso 1 1 calc R . . H2B H 0.2325 0.9327 1.1892 0.034 Uiso 1 1 calc R . . C3 C 0.47196(18) 0.87775(10) 1.10204(15) 0.0229(3) Uani 1 1 d . . . C4 C 0.71488(19) 0.82907(9) 0.93784(16) 0.0209(3) Uani 1 1 d . . . C5 C 0.67821(19) 0.80799(9) 0.75970(16) 0.0233(3) Uani 1 1 d . . . C6 C 0.8142(2) 0.74923(10) 0.70172(17) 0.0261(3) Uani 1 1 d . . . H6 H 0.7896 0.7361 0.5803 0.031 Uiso 1 1 calc R . . C7 C 0.98690(19) 0.70880(9) 0.81786(17) 0.0259(3) Uani 1 1 d . . . C8 C 1.1371(2) 0.64532(12) 0.7543(2) 0.0342(3) Uani 1 1 d . . . H8A H 1.1151 0.5726 0.7733 0.051 Uiso 1 1 calc R . . H8B H 1.2754 0.6644 0.8189 0.051 Uiso 1 1 calc R . . H8C H 1.1181 0.6577 0.6294 0.051 Uiso 1 1 calc R . . C9 C 0.3258(2) 1.04178(10) 0.84159(18) 0.0283(3) Uani 1 1 d . . . H9 H 0.3358 1.1164 0.8706 0.034 Uiso 1 1 calc R . . C10 C 0.2884(2) 1.02421(11) 0.64265(19) 0.0327(3) Uani 1 1 d . . . H10A H 0.2762 1.0884 0.5745 0.039 Uiso 1 1 calc R . . H10B H 0.1732 0.9779 0.5919 0.039 Uiso 1 1 calc R . . C11 C 0.49954(18) 0.97175(10) 0.67451(16) 0.0260(3) Uani 1 1 d . . . C12 C 0.4922(2) 0.85639(10) 0.63961(16) 0.0266(3) Uani 1 1 d . . . H12A H 0.3683 0.8267 0.6614 0.032 Uiso 1 1 calc R . . H12B H 0.4890 0.8432 0.5164 0.032 Uiso 1 1 calc R . . C13 C 1.0191(2) 0.72957(9) 0.99519(18) 0.0242(3) Uani 1 1 d . . . H13 H 1.1355 0.7015 1.0756 0.029 Uiso 1 1 calc R . . C14 C 0.88735(18) 0.78989(9) 1.05916(15) 0.0217(3) Uani 1 1 d . . . C15 C 0.9352(2) 0.81132(10) 1.25194(16) 0.0269(3) Uani 1 1 d . . . H15A H 1.0794 0.7983 1.3064 0.040 Uiso 1 1 calc R . . H15B H 0.8532 0.7666 1.3046 0.040 Uiso 1 1 calc R . . H15C H 0.9041 0.8830 1.2703 0.040 Uiso 1 1 calc R . . C16 C 0.53955(19) 0.99258(10) 0.87435(16) 0.0242(3) Uani 1 1 d . . . H16 H 0.6498 1.0442 0.9166 0.029 Uiso 1 1 calc R . . C17 C 0.6478(2) 1.02658(12) 0.59355(18) 0.0338(3) Uani 1 1 d . . . H17A H 0.6017 1.0203 0.4661 0.051 Uiso 1 1 calc R . . H17B H 0.7826 0.9957 0.6363 0.051 Uiso 1 1 calc R . . H17C H 0.6546 1.0991 0.6261 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0302(5) 0.0300(5) 0.0243(4) 0.0054(4) 0.0085(4) -0.0016(4) N1 0.0258(5) 0.0211(5) 0.0189(5) 0.0015(4) 0.0059(4) 0.0006(4) C1 0.0276(6) 0.0232(6) 0.0335(7) -0.0009(6) 0.0086(5) 0.0038(5) C2 0.0290(6) 0.0284(7) 0.0293(6) -0.0032(5) 0.0119(5) -0.0004(5) C3 0.0246(6) 0.0250(6) 0.0190(5) -0.0015(5) 0.0056(4) -0.0026(5) C4 0.0239(6) 0.0184(6) 0.0210(6) 0.0012(4) 0.0071(5) -0.0029(5) C5 0.0280(6) 0.0206(6) 0.0198(6) 0.0007(5) 0.0041(5) -0.0044(5) C6 0.0362(7) 0.0223(6) 0.0209(6) -0.0026(5) 0.0095(5) -0.0027(5) C7 0.0314(7) 0.0177(6) 0.0310(6) 0.0008(5) 0.0126(5) -0.0010(5) C8 0.0419(8) 0.0271(7) 0.0377(8) 0.0004(6) 0.0177(6) 0.0055(6) C9 0.0291(6) 0.0203(6) 0.0340(7) 0.0026(5) 0.0059(5) 0.0017(5) C10 0.0337(7) 0.0314(7) 0.0308(7) 0.0097(6) 0.0046(6) 0.0050(6) C11 0.0280(6) 0.0268(7) 0.0221(6) 0.0053(5) 0.0051(5) -0.0004(5) C12 0.0298(6) 0.0283(7) 0.0192(5) 0.0007(5) 0.0025(5) -0.0027(5) C13 0.0255(6) 0.0193(6) 0.0267(6) 0.0040(5) 0.0051(5) -0.0004(5) C14 0.0257(6) 0.0188(6) 0.0208(6) 0.0030(5) 0.0065(5) -0.0030(5) C15 0.0282(6) 0.0292(7) 0.0219(6) 0.0037(5) 0.0041(5) -0.0013(5) C16 0.0273(6) 0.0197(6) 0.0254(6) 0.0025(5) 0.0065(5) -0.0008(5) C17 0.0386(7) 0.0361(7) 0.0255(6) 0.0077(6) 0.0067(6) -0.0076(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.2283(16) . ? N1 C3 1.3632(16) . ? N1 C4 1.4315(15) . ? N1 C16 1.4770(16) . ? C1 C9 1.5196(18) . ? C1 C2 1.5324(19) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.5166(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C4 C5 1.3980(16) . ? C4 C14 1.4040(17) . ? C5 C6 1.3795(18) . ? C5 C12 1.5089(17) . ? C6 C7 1.3928(19) . ? C6 H6 0.9500 . ? C7 C13 1.3942(19) . ? C7 C8 1.5113(18) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5503(19) . ? C9 C16 1.5552(18) . ? C9 H9 1.0000 . ? C10 C11 1.5578(18) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C17 1.5213(17) . ? C11 C12 1.5314(19) . ? C11 C16 1.5623(17) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.3945(18) . ? C13 H13 0.9500 . ? C14 C15 1.5052(17) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 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 C3 N1 C4 123.44(11) . . ? C3 N1 C16 122.48(10) . . ? C4 N1 C16 113.78(9) . . ? C9 C1 C2 107.48(10) . . ? C9 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? C9 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? C3 C2 C1 108.80(10) . . ? C3 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? C3 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? O1 C3 N1 122.72(12) . . ? O1 C3 C2 122.56(11) . . ? N1 C3 C2 114.64(11) . . ? C5 C4 C14 120.76(11) . . ? C5 C4 N1 115.42(10) . . ? C14 C4 N1 123.59(10) . . ? C6 C5 C4 119.77(12) . . ? C6 C5 C12 123.55(11) . . ? C4 C5 C12 116.62(11) . . ? C5 C6 C7 121.23(12) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C6 C7 C13 118.07(12) . . ? C6 C7 C8 121.26(12) . . ? C13 C7 C8 120.67(12) . . ? 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 . . ? C1 C9 C10 118.31(11) . . ? C1 C9 C16 113.38(10) . . ? C10 C9 C16 89.84(10) . . ? C1 C9 H9 111.2 . . ? C10 C9 H9 111.2 . . ? C16 C9 H9 111.2 . . ? C9 C10 C11 90.57(10) . . ? C9 C10 H10A 113.5 . . ? C11 C10 H10A 113.5 . . ? C9 C10 H10B 113.5 . . ? C11 C10 H10B 113.5 . . ? H10A C10 H10B 110.8 . . ? C17 C11 C12 112.34(12) . . ? C17 C11 C10 114.87(11) . . ? C12 C11 C10 114.85(11) . . ? C17 C11 C16 113.31(11) . . ? C12 C11 C16 110.13(10) . . ? C10 C11 C16 89.31(10) . . ? C5 C12 C11 108.50(10) . . ? C5 C12 H12A 110.0 . . ? C11 C12 H12A 110.0 . . ? C5 C12 H12B 110.0 . . ? C11 C12 H12B 110.0 . . ? H12A C12 H12B 108.4 . . ? C7 C13 C14 122.60(12) . . ? C7 C13 H13 118.7 . . ? C14 C13 H13 118.7 . . ? C13 C14 C4 117.56(11) . . ? C13 C14 C15 119.57(11) . . ? C4 C14 C15 122.87(11) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 C9 116.34(10) . . ? N1 C16 C11 113.86(10) . . ? C9 C16 C11 90.23(10) . . ? N1 C16 H16 111.6 . . ? C9 C16 H16 111.6 . . ? C11 C16 H16 111.6 . . ? C11 C17 H17A 109.5 . . ? C11 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C11 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 68.11 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.212 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.075 data_2c-S,S,S _database_code_depnum_ccdc_archive 'CCDC 903371' #TrackingRef 'XRD_Structures_5_compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 N O' _chemical_formula_sum 'C17 H21 N O' _chemical_formula_weight 255.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.8456(2) _cell_length_b 13.0609(3) _cell_length_c 7.9584(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.8150(10) _cell_angle_gamma 90.00 _cell_volume 684.62(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6514 _cell_measurement_theta_min 6.70 _cell_measurement_theta_max 68.00 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.590 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8126 _exptl_absorpt_correction_T_max 0.9494 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7269 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 6.70 _diffrn_reflns_theta_max 68.00 _reflns_number_total 2403 _reflns_number_gt 2376 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.0972P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 2403 _refine_ls_number_parameters 175 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0281 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0732 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.00634(13) 0.78704(7) 1.18468(11) 0.0286(2) Uani 1 1 d . . . N1 N 0.07658(15) 0.68497(8) 0.98280(13) 0.0229(2) Uani 1 1 d . . . C1 C 0.6371(2) 0.93861(12) 0.7539(2) 0.0343(3) Uani 1 1 d . . . H1A H 0.7757 0.9198 0.8189 0.051 Uiso 1 1 calc R . . H1B H 0.6146 1.0114 0.7721 0.051 Uiso 1 1 calc R . . H1C H 0.6182 0.9258 0.6291 0.051 Uiso 1 1 calc R . . C2 C 0.4871(2) 0.87519(9) 0.81775(18) 0.0263(3) Uani 1 1 d . . . C3 C 0.3140(2) 0.83460(10) 0.70134(17) 0.0266(3) Uani 1 1 d . . . H3 H 0.2892 0.8476 0.5799 0.032 Uiso 1 1 calc R . . C4 C 0.1781(2) 0.77590(9) 0.75979(16) 0.0243(3) Uani 1 1 d . . . C5 C -0.0080(2) 0.72730(10) 0.63963(17) 0.0271(3) Uani 1 1 d . . . H5A H -0.0110 0.7403 0.5164 0.033 Uiso 1 1 calc R . . H5B H -0.1321 0.7571 0.6609 0.033 Uiso 1 1 calc R . . C6 C -0.00083(19) 0.61190(10) 0.67505(16) 0.0266(3) Uani 1 1 d . . . C7 C -0.2119(2) 0.55944(11) 0.64331(19) 0.0328(3) Uani 1 1 d . . . H7A H -0.3273 0.6058 0.5924 0.039 Uiso 1 1 calc R . . H7B H -0.2243 0.4951 0.5754 0.039 Uiso 1 1 calc R . . C8 C -0.1744(2) 0.54208(9) 0.84194(18) 0.0285(3) Uani 1 1 d . . . H8 H -0.1642 0.4675 0.8711 0.034 Uiso 1 1 calc R . . C9 C -0.31001(19) 0.59719(10) 0.93521(17) 0.0281(3) Uani 1 1 d . . . H9A H -0.4236 0.5522 0.9431 0.034 Uiso 1 1 calc R . . H9B H -0.3673 0.6599 0.8703 0.034 Uiso 1 1 calc R . . C10 C 0.5195(2) 0.85451(9) 0.99485(18) 0.0248(3) Uani 1 1 d . . . H10 H 0.6361 0.8826 1.0752 0.030 Uiso 1 1 calc R . . C11 C 0.38790(19) 0.79422(9) 1.05921(16) 0.0226(3) Uani 1 1 d . . . C12 C 0.21536(19) 0.75509(9) 0.93777(17) 0.0216(3) Uani 1 1 d . . . C13 C 0.03955(19) 0.59139(10) 0.87463(17) 0.0248(3) Uani 1 1 d . . . H13 H 0.1499 0.5398 0.9170 0.030 Uiso 1 1 calc R . . C14 C -0.1796(2) 0.62507(10) 1.11822(18) 0.0286(3) Uani 1 1 d . . . H14A H -0.2668 0.6513 1.1894 0.034 Uiso 1 1 calc R . . H14B H -0.1074 0.5636 1.1766 0.034 Uiso 1 1 calc R . . C15 C -0.02720(18) 0.70644(10) 1.10235(15) 0.0234(3) Uani 1 1 d . . . C16 C 0.1471(2) 0.55677(12) 0.59406(18) 0.0340(3) Uani 1 1 d . . . H16A H 0.2821 0.5875 0.6366 0.051 Uiso 1 1 calc R . . H16B H 0.1006 0.5630 0.4666 0.051 Uiso 1 1 calc R . . H16C H 0.1537 0.4842 0.6267 0.051 Uiso 1 1 calc R . . C17 C 0.4364(2) 0.77311(10) 1.25189(16) 0.0271(3) Uani 1 1 d . . . H17A H 0.3539 0.8176 1.3044 0.041 Uiso 1 1 calc R . . H17B H 0.5806 0.7866 1.3063 0.041 Uiso 1 1 calc R . . H17C H 0.4063 0.7013 1.2706 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0301(5) 0.0275(5) 0.0285(4) -0.0053(4) 0.0085(4) 0.0015(4) N1 0.0254(5) 0.0194(5) 0.0235(5) -0.0011(4) 0.0058(4) -0.0004(4) C1 0.0414(8) 0.0247(6) 0.0401(8) -0.0001(6) 0.0169(6) -0.0049(6) C2 0.0307(7) 0.0154(6) 0.0344(7) -0.0006(5) 0.0114(5) 0.0010(5) C3 0.0355(7) 0.0196(6) 0.0250(6) 0.0028(5) 0.0089(5) 0.0025(5) C4 0.0283(7) 0.0186(6) 0.0245(6) 0.0000(5) 0.0047(5) 0.0047(5) C5 0.0298(7) 0.0257(7) 0.0235(6) -0.0007(5) 0.0033(5) 0.0026(5) C6 0.0272(6) 0.0251(7) 0.0261(6) -0.0046(5) 0.0048(5) 0.0011(5) C7 0.0336(7) 0.0281(7) 0.0337(7) -0.0092(6) 0.0041(6) -0.0050(6) C8 0.0290(7) 0.0177(6) 0.0370(7) -0.0017(5) 0.0059(5) -0.0012(5) C9 0.0271(6) 0.0201(6) 0.0363(7) 0.0016(6) 0.0074(5) -0.0035(5) C10 0.0254(6) 0.0168(6) 0.0306(6) -0.0040(5) 0.0050(5) 0.0006(5) C11 0.0257(6) 0.0163(6) 0.0255(6) -0.0029(5) 0.0067(5) 0.0032(5) C12 0.0237(6) 0.0154(6) 0.0261(6) -0.0012(5) 0.0077(5) 0.0032(5) C13 0.0275(6) 0.0173(6) 0.0288(6) -0.0021(5) 0.0066(5) 0.0013(5) C14 0.0286(7) 0.0261(7) 0.0329(7) 0.0030(6) 0.0116(5) 0.0008(5) C15 0.0242(6) 0.0226(6) 0.0226(6) 0.0016(5) 0.0048(5) 0.0027(5) C16 0.0379(7) 0.0334(7) 0.0290(7) -0.0067(6) 0.0061(6) 0.0070(6) C17 0.0275(6) 0.0261(7) 0.0261(7) -0.0037(5) 0.0047(5) 0.0012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.2276(16) . ? N1 C15 1.3627(16) . ? N1 C12 1.4337(16) . ? N1 C13 1.4765(16) . ? C1 C2 1.5110(18) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C10 1.3922(19) . ? C2 C3 1.3947(19) . ? C3 C4 1.3805(19) . ? C3 H3 0.9500 . ? C4 C12 1.3958(17) . ? C4 C5 1.5089(17) . ? C5 C6 1.5317(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C16 1.5213(18) . ? C6 C7 1.5565(19) . ? C6 C13 1.5594(17) . ? C7 C8 1.5475(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5187(18) . ? C8 C13 1.5556(18) . ? C8 H8 1.0000 . ? C9 C14 1.5305(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.3950(19) . ? C10 H10 0.9500 . ? C11 C12 1.4029(17) . ? C11 C17 1.5034(17) . ? C13 H13 1.0000 . ? C14 C15 1.5182(18) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 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 C15 N1 C12 123.38(11) . . ? C15 N1 C13 122.55(10) . . ? C12 N1 C13 113.78(10) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C10 C2 C3 118.09(12) . . ? C10 C2 C1 120.77(12) . . ? C3 C2 C1 121.13(12) . . ? C4 C3 C2 121.06(12) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C12 119.77(12) . . ? C3 C4 C5 123.39(12) . . ? C12 C4 C5 116.77(11) . . ? C4 C5 C6 108.55(10) . . ? C4 C5 H5A 110.0 . . ? C6 C5 H5A 110.0 . . ? C4 C5 H5B 110.0 . . ? C6 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? C16 C6 C5 112.30(12) . . ? C16 C6 C7 114.74(12) . . ? C5 C6 C7 114.93(11) . . ? C16 C6 C13 113.37(11) . . ? C5 C6 C13 110.14(10) . . ? C7 C6 C13 89.35(10) . . ? C8 C7 C6 90.60(10) . . ? C8 C7 H7A 113.5 . . ? C6 C7 H7A 113.5 . . ? C8 C7 H7B 113.5 . . ? C6 C7 H7B 113.5 . . ? H7A C7 H7B 110.8 . . ? C9 C8 C7 118.44(11) . . ? C9 C8 C13 113.27(10) . . ? C7 C8 C13 89.82(10) . . ? C9 C8 H8 111.2 . . ? C7 C8 H8 111.2 . . ? C13 C8 H8 111.2 . . ? C8 C9 C14 107.58(10) . . ? C8 C9 H9A 110.2 . . ? C14 C9 H9A 110.2 . . ? C8 C9 H9B 110.2 . . ? C14 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? C2 C10 C11 122.72(12) . . ? C2 C10 H10 118.6 . . ? C11 C10 H10 118.6 . . ? C10 C11 C12 117.35(11) . . ? C10 C11 C17 119.53(11) . . ? C12 C11 C17 123.11(11) . . ? C4 C12 C11 120.99(11) . . ? C4 C12 N1 115.33(11) . . ? C11 C12 N1 123.46(11) . . ? N1 C13 C8 116.39(11) . . ? N1 C13 C6 113.98(10) . . ? C8 C13 C6 90.19(10) . . ? N1 C13 H13 111.6 . . ? C8 C13 H13 111.6 . . ? C6 C13 H13 111.6 . . ? C15 C14 C9 108.86(10) . . ? C15 C14 H14A 109.9 . . ? C9 C14 H14A 109.9 . . ? C15 C14 H14B 109.9 . . ? C9 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? O1 C15 N1 122.83(12) . . ? O1 C15 C14 122.58(11) . . ? N1 C15 C14 114.51(11) . . ? C6 C16 H16A 109.5 . . ? C6 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C6 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C17 H17A 109.5 . . ? C11 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C11 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 68.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.147 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.030 data_3b _database_code_depnum_ccdc_archive 'CCDC 903372' #TrackingRef 'XRD_Structures_5_compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 N O' _chemical_formula_sum 'C17 H21 N O' _chemical_formula_weight 255.35 _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _space_group_name_Hall '-P 1' _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3999(7) _cell_length_b 9.6886(6) _cell_length_c 16.2607(10) _cell_angle_alpha 100.547(3) _cell_angle_beta 98.903(3) _cell_angle_gamma 103.446(3) _cell_volume 1385.48(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9916 _cell_measurement_theta_min 4.82 _cell_measurement_theta_max 69.29 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.583 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8300 _exptl_absorpt_correction_T_max 0.9805 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 34128 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 69.78 _reflns_number_total 4965 _reflns_number_gt 4361 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.8876P] 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 4965 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.17972(13) 0.00452(12) 1.28925(8) 0.0302(3) Uani 1 1 d . . . O2 O 0.30711(13) 1.09249(12) 0.60065(7) 0.0296(3) Uani 1 1 d . . . N1 N -0.03380(15) -0.18154(13) 1.25962(8) 0.0227(3) Uani 1 1 d . . . N2 N 0.51893(15) 1.20474(13) 0.70282(8) 0.0218(3) Uani 1 1 d . . . C1 C -0.10668(18) -0.15514(18) 1.03217(10) 0.0269(4) Uani 1 1 d . . . H1 H -0.1153 -0.0854 0.9989 0.032 Uiso 1 1 calc R . . C2 C -0.07414(18) -0.11024(17) 1.12121(10) 0.0248(3) Uani 1 1 d . . . C3 C -0.05950(17) -0.21528(17) 1.16851(10) 0.0223(3) Uani 1 1 d . . . C4 C -0.08200(18) -0.36233(17) 1.12775(10) 0.0234(3) Uani 1 1 d . . . C5 C -0.0672(2) -0.47294(17) 1.18128(10) 0.0264(4) Uani 1 1 d . . . H5A H 0.0395 -0.4583 1.2068 0.032 Uiso 1 1 calc R . . H5B H -0.1059 -0.5728 1.1447 0.032 Uiso 1 1 calc R . . C6 C -0.15540(18) -0.45497(17) 1.25202(10) 0.0248(3) Uani 1 1 d . . . H6 H -0.2659 -0.4950 1.2311 0.030 Uiso 1 1 calc R . . C7 C -0.09591(18) -0.48902(17) 1.34094(10) 0.0249(3) Uani 1 1 d . . . C8 C -0.2198(2) -0.51760(19) 1.39039(12) 0.0332(4) Uani 1 1 d . . . H8A H -0.2948 -0.6088 1.3605 0.050 Uiso 1 1 calc R . . H8B H -0.2668 -0.4370 1.3948 0.050 Uiso 1 1 calc R . . H8C H -0.1778 -0.5255 1.4478 0.050 Uiso 1 1 calc R . . C9 C -0.0155(2) -0.6095(2) 1.33812(12) 0.0343(4) Uani 1 1 d . . . H9A H 0.0279 -0.6118 1.3965 0.051 Uiso 1 1 calc R . . H9B H 0.0642 -0.5903 1.3060 0.051 Uiso 1 1 calc R . . H9C H -0.0870 -0.7037 1.3100 0.051 Uiso 1 1 calc R . . C10 C -0.12668(18) -0.29860(18) 0.99122(10) 0.0275(4) Uani 1 1 d . . . H10 H -0.1471 -0.3263 0.9306 0.033 Uiso 1 1 calc R . . C11 C -0.11678(18) -0.40190(18) 1.03909(10) 0.0264(4) Uani 1 1 d . . . H11 H -0.1340 -0.5010 1.0108 0.032 Uiso 1 1 calc R . . C12 C -0.0598(2) 0.04511(18) 1.16347(11) 0.0314(4) Uani 1 1 d . . . H12A H 0.0461 0.0991 1.1800 0.047 Uiso 1 1 calc R . . H12B H -0.1036 0.0477 1.2145 0.047 Uiso 1 1 calc R . . H12C H -0.1125 0.0899 1.1235 0.047 Uiso 1 1 calc R . . C13 C 0.08391(18) -0.07674(16) 1.31438(10) 0.0250(3) Uani 1 1 d . . . C14 C 0.0814(2) -0.06444(18) 1.40968(11) 0.0333(4) Uani 1 1 d . . . H14A H 0.0034 -0.0155 1.4227 0.040 Uiso 1 1 calc R . . H14B H 0.1786 0.0008 1.4430 0.040 Uiso 1 1 calc R . . C15 C 0.0526(2) -0.20831(19) 1.44371(11) 0.0346(4) Uani 1 1 d . . . H15A H 0.1450 -0.2140 1.4799 0.041 Uiso 1 1 calc R . . H15B H -0.0264 -0.2125 1.4777 0.041 Uiso 1 1 calc R . . C16 C 0.0040(2) -0.32975(18) 1.36499(10) 0.0297(4) Uani 1 1 d . . . H16 H 0.0943 -0.3308 1.3397 0.036 Uiso 1 1 calc R . . C17 C -0.10869(18) -0.29390(16) 1.29936(10) 0.0233(3) Uani 1 1 d . . . H17 H -0.1908 -0.2658 1.3250 0.028 Uiso 1 1 calc R . . C18 C 0.71544(19) 1.13939(19) 0.95016(11) 0.0296(4) Uani 1 1 d . . . H18A H 0.7893 1.2144 0.9953 0.044 Uiso 1 1 calc R . . H18B H 0.7637 1.1073 0.9036 0.044 Uiso 1 1 calc R . . H18C H 0.6740 1.0561 0.9736 0.044 Uiso 1 1 calc R . . C19 C 0.59032(18) 1.20196(17) 0.91599(10) 0.0239(3) Uani 1 1 d . . . C20 C 0.64601(17) 1.31571(16) 0.86136(9) 0.0210(3) Uani 1 1 d . . . H20 H 0.7565 1.3606 0.8763 0.025 Uiso 1 1 calc R . . C21 C 0.55514(18) 1.42421(16) 0.84585(10) 0.0225(3) Uani 1 1 d . . . H21A H 0.4484 1.3803 0.8445 0.027 Uiso 1 1 calc R . . H21B H 0.5914 1.5132 0.8926 0.027 Uiso 1 1 calc R . . C22 C 0.57306(17) 1.46270(16) 0.76136(10) 0.0219(3) Uani 1 1 d . . . C23 C 0.54984(17) 1.34908(16) 0.68874(10) 0.0215(3) Uani 1 1 d . . . C24 C 0.56954(18) 1.37737(17) 0.60949(10) 0.0246(3) Uani 1 1 d . . . C25 C 0.5526(2) 1.25727(19) 0.53250(10) 0.0318(4) Uani 1 1 d . . . H25A H 0.5953 1.1814 0.5501 0.048 Uiso 1 1 calc R . . H25B H 0.6052 1.2970 0.4909 0.048 Uiso 1 1 calc R . . H25C H 0.4463 1.2152 0.5064 0.048 Uiso 1 1 calc R . . C26 C 0.4397(2) 0.94651(17) 0.78635(11) 0.0298(4) Uani 1 1 d . . . H26A H 0.3512 0.8945 0.8051 0.036 Uiso 1 1 calc R . . H26B H 0.5219 0.9006 0.7990 0.036 Uiso 1 1 calc R . . C27 C 0.4013(2) 0.94402(17) 0.68820(11) 0.0325(4) Uani 1 1 d . . . H27A H 0.4727 0.9010 0.6607 0.039 Uiso 1 1 calc R . . H27B H 0.3007 0.8763 0.6644 0.039 Uiso 1 1 calc R . . C28 C 0.40216(18) 1.08763(17) 0.65987(10) 0.0249(3) Uani 1 1 d . . . C29 C 0.59606(18) 1.18689(16) 0.78367(9) 0.0217(3) Uani 1 1 d . . . H29 H 0.6777 1.1387 0.7755 0.026 Uiso 1 1 calc R . . C30 C 0.48690(18) 1.10645(17) 0.82987(10) 0.0249(3) Uani 1 1 d . . . H30 H 0.3957 1.1428 0.8215 0.030 Uiso 1 1 calc R . . C31 C 0.61586(18) 1.60593(17) 0.75300(10) 0.0252(3) Uani 1 1 d . . . H31 H 0.6328 1.6837 0.8015 0.030 Uiso 1 1 calc R . . C32 C 0.63420(18) 1.63673(17) 0.67459(11) 0.0272(4) Uani 1 1 d . . . H32 H 0.6624 1.7349 0.6693 0.033 Uiso 1 1 calc R . . C33 C 0.61102(18) 1.52317(18) 0.60424(10) 0.0270(4) Uani 1 1 d . . . H33 H 0.6237 1.5450 0.5508 0.032 Uiso 1 1 calc R . . C34 C 0.5142(2) 1.25315(19) 0.98744(11) 0.0313(4) Uani 1 1 d . . . H34A H 0.4754 1.1714 1.0127 0.047 Uiso 1 1 calc R . . H34B H 0.4315 1.2898 0.9641 0.047 Uiso 1 1 calc R . . H34C H 0.5867 1.3312 1.0315 0.047 Uiso 1 1 calc R . . _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0272(7) 0.0208(5) 0.0386(7) 0.0009(5) 0.0064(5) 0.0038(5) O2 0.0275(7) 0.0298(6) 0.0244(6) -0.0025(5) -0.0016(5) 0.0053(5) N1 0.0240(7) 0.0209(6) 0.0207(6) 0.0011(5) 0.0046(5) 0.0043(5) N2 0.0231(7) 0.0189(6) 0.0207(6) 0.0013(5) 0.0007(5) 0.0053(5) C1 0.0197(8) 0.0335(9) 0.0289(8) 0.0119(7) 0.0047(6) 0.0061(7) C2 0.0189(8) 0.0273(8) 0.0287(8) 0.0065(7) 0.0065(6) 0.0058(6) C3 0.0181(8) 0.0258(8) 0.0214(7) 0.0026(6) 0.0045(6) 0.0044(6) C4 0.0195(8) 0.0247(8) 0.0235(8) 0.0018(6) 0.0037(6) 0.0042(6) C5 0.0300(9) 0.0238(8) 0.0237(8) 0.0013(6) 0.0042(7) 0.0079(7) C6 0.0225(8) 0.0250(8) 0.0256(8) 0.0034(6) 0.0031(6) 0.0068(6) C7 0.0229(9) 0.0263(8) 0.0240(8) 0.0052(6) 0.0028(6) 0.0052(7) C8 0.0332(10) 0.0317(9) 0.0384(10) 0.0120(7) 0.0119(8) 0.0102(8) C9 0.0324(10) 0.0363(9) 0.0361(9) 0.0100(8) 0.0055(8) 0.0129(8) C10 0.0194(8) 0.0378(9) 0.0212(8) 0.0042(7) 0.0022(6) 0.0032(7) C11 0.0225(9) 0.0269(8) 0.0240(8) -0.0010(6) 0.0029(6) 0.0020(7) C12 0.0362(10) 0.0272(8) 0.0335(9) 0.0085(7) 0.0086(8) 0.0116(7) C13 0.0247(9) 0.0194(7) 0.0285(8) -0.0009(6) 0.0036(7) 0.0073(6) C14 0.0407(11) 0.0255(8) 0.0258(9) -0.0032(7) -0.0001(7) 0.0053(7) C15 0.0385(11) 0.0302(9) 0.0287(9) 0.0005(7) -0.0014(8) 0.0072(8) C16 0.0302(10) 0.0297(9) 0.0268(8) 0.0061(7) 0.0024(7) 0.0060(7) C17 0.0228(8) 0.0230(8) 0.0221(7) 0.0025(6) 0.0060(6) 0.0038(6) C18 0.0254(9) 0.0331(9) 0.0318(9) 0.0122(7) 0.0030(7) 0.0089(7) C19 0.0208(8) 0.0257(8) 0.0247(8) 0.0065(6) 0.0034(6) 0.0054(6) C20 0.0180(8) 0.0228(7) 0.0204(7) 0.0019(6) 0.0025(6) 0.0051(6) C21 0.0210(8) 0.0211(7) 0.0232(8) 0.0006(6) 0.0025(6) 0.0063(6) C22 0.0171(8) 0.0224(7) 0.0242(8) 0.0027(6) 0.0004(6) 0.0064(6) C23 0.0177(8) 0.0198(7) 0.0248(8) 0.0030(6) 0.0008(6) 0.0049(6) C24 0.0206(8) 0.0273(8) 0.0243(8) 0.0039(6) 0.0016(6) 0.0066(6) C25 0.0374(10) 0.0325(9) 0.0242(8) 0.0043(7) 0.0069(7) 0.0083(8) C26 0.0299(10) 0.0228(8) 0.0357(9) 0.0065(7) 0.0066(7) 0.0054(7) C27 0.0373(10) 0.0206(8) 0.0333(9) -0.0007(7) 0.0034(8) 0.0029(7) C28 0.0249(9) 0.0220(8) 0.0240(8) -0.0023(6) 0.0048(7) 0.0051(6) C29 0.0215(8) 0.0204(7) 0.0220(7) 0.0025(6) 0.0016(6) 0.0074(6) C30 0.0221(9) 0.0240(8) 0.0278(8) 0.0055(6) 0.0033(6) 0.0062(6) C31 0.0224(8) 0.0201(7) 0.0299(8) 0.0017(6) -0.0003(6) 0.0066(6) C32 0.0215(9) 0.0230(8) 0.0360(9) 0.0102(7) 0.0006(7) 0.0047(6) C33 0.0236(9) 0.0302(8) 0.0276(8) 0.0108(7) 0.0030(7) 0.0060(7) C34 0.0292(10) 0.0369(9) 0.0287(9) 0.0084(7) 0.0094(7) 0.0080(7) _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. ; _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.225(2) . ? O2 C28 1.224(2) . ? N1 C13 1.375(2) . ? N1 C3 1.4267(19) . ? N1 C17 1.463(2) . ? N2 C28 1.369(2) . ? N2 C23 1.4287(19) . ? N2 C29 1.4597(19) . ? C1 C10 1.383(2) . ? C1 C2 1.396(2) . ? C1 H1 0.9500 . ? C2 C3 1.402(2) . ? C2 C12 1.501(2) . ? C3 C4 1.409(2) . ? C4 C11 1.388(2) . ? C4 C5 1.516(2) . ? C5 C6 1.527(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C17 1.535(2) . ? C6 C7 1.588(2) . ? C6 H6 1.0000 . ? C7 C8 1.517(2) . ? C7 C9 1.529(2) . ? C7 C16 1.552(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.536(2) . ? C14 C15 1.574(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.500(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.529(2) . ? C16 H16 1.0000 . ? C17 H17 1.0000 . ? C18 C19 1.521(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C34 1.523(2) . ? C19 C30 1.565(2) . ? C19 C20 1.585(2) . ? C20 C29 1.530(2) . ? C20 C21 1.532(2) . ? C20 H20 1.0000 . ? C21 C22 1.512(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C31 1.390(2) . ? C22 C23 1.409(2) . ? C23 C24 1.396(2) . ? C24 C33 1.398(2) . ? C24 C25 1.505(2) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C30 1.510(2) . ? C26 C27 1.575(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.542(2) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C29 C30 1.518(2) . ? C29 H29 1.0000 . ? C30 H30 1.0000 . ? C31 C32 1.388(2) . ? C31 H31 0.9500 . ? C32 C33 1.385(2) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? _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 C13 N1 C3 126.32(13) . . ? C13 N1 C17 114.03(13) . . ? C3 N1 C17 116.77(12) . . ? C28 N2 C23 127.43(13) . . ? C28 N2 C29 114.16(13) . . ? C23 N2 C29 116.59(12) . . ? C10 C1 C2 121.67(15) . . ? C10 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C1 C2 C3 117.79(15) . . ? C1 C2 C12 120.18(15) . . ? C3 C2 C12 122.01(14) . . ? C2 C3 C4 121.20(14) . . ? C2 C3 N1 121.88(14) . . ? C4 C3 N1 116.71(13) . . ? C11 C4 C3 118.75(15) . . ? C11 C4 C5 121.69(14) . . ? C3 C4 C5 119.56(14) . . ? C4 C5 C6 109.46(13) . . ? C4 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? C4 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? C5 C6 C17 108.50(13) . . ? C5 C6 C7 118.72(14) . . ? C17 C6 C7 86.63(11) . . ? C5 C6 H6 113.3 . . ? C17 C6 H6 113.3 . . ? C7 C6 H6 113.3 . . ? C8 C7 C9 110.03(14) . . ? C8 C7 C16 114.66(14) . . ? C9 C7 C16 116.76(14) . . ? C8 C7 C6 110.97(14) . . ? C9 C7 C6 116.73(13) . . ? C16 C7 C6 85.91(11) . . ? 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 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 C11 119.70(15) . . ? C1 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C4 120.83(15) . . ? C10 C11 H11 119.6 . . ? C4 C11 H11 119.6 . . ? C2 C12 H12A 109.5 . . ? C2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 N1 122.73(15) . . ? O1 C13 C14 122.57(15) . . ? N1 C13 C14 114.63(14) . . ? C13 C14 C15 118.34(14) . . ? C13 C14 H14A 107.7 . . ? C15 C14 H14A 107.7 . . ? C13 C14 H14B 107.7 . . ? C15 C14 H14B 107.7 . . ? H14A C14 H14B 107.1 . . ? C16 C15 C14 105.01(14) . . ? C16 C15 H15A 110.7 . . ? C14 C15 H15A 110.7 . . ? C16 C15 H15B 110.7 . . ? C14 C15 H15B 110.7 . . ? H15A C15 H15B 108.8 . . ? C15 C16 C17 109.22(14) . . ? C15 C16 C7 135.69(15) . . ? C17 C16 C7 88.16(12) . . ? C15 C16 H16 106.6 . . ? C17 C16 H16 106.6 . . ? C7 C16 H16 106.6 . . ? N1 C17 C16 110.88(13) . . ? N1 C17 C6 120.36(13) . . ? C16 C17 C6 88.56(12) . . ? N1 C17 H17 111.6 . . ? C16 C17 H17 111.6 . . ? C6 C17 H17 111.6 . . ? C19 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C19 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C18 C19 C34 110.33(13) . . ? C18 C19 C30 113.99(13) . . ? C34 C19 C30 117.18(14) . . ? C18 C19 C20 111.11(13) . . ? C34 C19 C20 116.67(13) . . ? C30 C19 C20 85.64(11) . . ? C29 C20 C21 108.03(12) . . ? C29 C20 C19 86.76(11) . . ? C21 C20 C19 118.31(13) . . ? C29 C20 H20 113.6 . . ? C21 C20 H20 113.6 . . ? C19 C20 H20 113.6 . . ? C22 C21 C20 108.48(12) . . ? C22 C21 H21A 110.0 . . ? C20 C21 H21A 110.0 . . ? C22 C21 H21B 110.0 . . ? C20 C21 H21B 110.0 . . ? H21A C21 H21B 108.4 . . ? C31 C22 C23 118.67(14) . . ? C31 C22 C21 122.54(14) . . ? C23 C22 C21 118.76(13) . . ? C24 C23 C22 121.58(14) . . ? C24 C23 N2 122.07(14) . . ? C22 C23 N2 116.10(13) . . ? C23 C24 C33 117.51(15) . . ? C23 C24 C25 122.13(14) . . ? C33 C24 C25 120.32(14) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C30 C26 C27 104.35(13) . . ? C30 C26 H26A 110.9 . . ? C27 C26 H26A 110.9 . . ? C30 C26 H26B 110.9 . . ? C27 C26 H26B 110.9 . . ? H26A C26 H26B 108.9 . . ? C28 C27 C26 119.50(13) . . ? C28 C27 H27A 107.4 . . ? C26 C27 H27A 107.4 . . ? C28 C27 H27B 107.4 . . ? C26 C27 H27B 107.4 . . ? H27A C27 H27B 107.0 . . ? O2 C28 N2 123.39(15) . . ? O2 C28 C27 121.20(14) . . ? N2 C28 C27 115.35(14) . . ? N2 C29 C30 111.28(13) . . ? N2 C29 C20 119.40(12) . . ? C30 C29 C20 89.21(12) . . ? N2 C29 H29 111.7 . . ? C30 C29 H29 111.7 . . ? C20 C29 H29 111.7 . . ? C26 C30 C29 108.62(13) . . ? C26 C30 C19 135.69(14) . . ? C29 C30 C19 87.88(12) . . ? C26 C30 H30 106.9 . . ? C29 C30 H30 106.9 . . ? C19 C30 H30 106.9 . . ? C32 C31 C22 120.77(15) . . ? C32 C31 H31 119.6 . . ? C22 C31 H31 119.6 . . ? C33 C32 C31 119.44(15) . . ? C33 C32 H32 120.3 . . ? C31 C32 H32 120.3 . . ? C32 C33 C24 122.00(15) . . ? C32 C33 H33 119.0 . . ? C24 C33 H33 119.0 . . ? C19 C34 H34A 109.5 . . ? C19 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C19 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 69.78 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.646 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.039