# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1248 data_2b _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C15 H21 N O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H22 N O2.50' _chemical_formula_weight 256.34 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .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 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.840(1) _cell_length_b 18.077(1) _cell_length_c 12.920(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.62(1) _cell_angle_gamma 90.00 _cell_volume 2998.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method ? _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'nonius kappa-ccd diffractometer' _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11448 _diffrn_reflns_av_R_equivalents 0.0665 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.10 _reflns_number_total 3199 _reflns_number_observed 1748 _reflns_observed_criterion 2sigma(I) _computing_data_collection 'nonius collect' _computing_cell_refinement 'nonius denzo' _computing_data_reduction 'nonius denzo' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'xtal' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 83 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[s^2^(Fo^2^)+( 0.0619P)^2^+0.5637P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3116 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1256 _refine_ls_R_factor_obs 0.0581 _refine_ls_wR_factor_all 0.1422 _refine_ls_wR_factor_obs 0.1175 _refine_ls_goodness_of_fit_all 1.029 _refine_ls_goodness_of_fit_obs 1.221 _refine_ls_restrained_S_all 1.059 _refine_ls_restrained_S_obs 1.221 _refine_ls_shift/esd_max 0.652 _refine_ls_shift/esd_mean 0.072 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C -0.1020(2) 0.4086(2) 1.0221(3) 0.0670(8) Uani 1 d . . H1A H -0.1358(36) 0.3878(26) 1.0737(37) 0.166(19) Uiso 1 d . . H1B H -0.1359(28) 0.4056(18) 0.9650(30) 0.121(13) Uiso 1 d . . H1C H -0.1107(36) 0.4561(31) 1.0560(39) 0.192(20) Uiso 1 d . . C2 C 0.0095(2) 0.38626(11) 1.0157(2) 0.0459(5) Uani 1 d . . N3 N 0.03934(15) 0.35376(10) 0.92725(14) 0.0460(5) Uani 1 d . . H3 H -0.0072(20) 0.3542(14) 0.8775(21) 0.073(8) Uiso 1 d . . C4 C 0.1449(2) 0.33375(11) 0.9053(2) 0.0424(5) Uani 1 d . . H4 H 0.1841(14) 0.3350(9) 0.9708(14) 0.034(5) Uiso 1 d . . C5 C 0.2020(2) 0.37813(11) 0.82001(14) 0.0396(5) Uani 1 d . . O6 O 0.12901(12) 0.39497(9) 0.73903(10) 0.0467(4) Uani 1 d . . C7 C 0.2572(2) 0.30376(11) 0.7893(2) 0.0475(6) Uani 1 d . . C8 C 0.3607(2) 0.2934(2) 0.8465(2) 0.0633(7) Uani 1 d . . H8A H 0.3822(20) 0.2448(16) 0.8361(18) 0.072(8) Uiso 1 d . . H8B H 0.3581(18) 0.3024(13) 0.9236(21) 0.073(8) Uiso 1 d . . H8C H 0.4124(21) 0.3284(16) 0.8199(19) 0.084(9) Uiso 1 d . . C9 C 0.2704(3) 0.2891(2) 0.6743(2) 0.0689(8) Uani 1 d . . H9A H 0.2020(27) 0.2937(17) 0.6328(23) 0.108(11) Uiso 1 d . . H9B H 0.2989(22) 0.2383(18) 0.6635(20) 0.095(9) Uiso 1 d . . H9C H 0.3234(23) 0.3233(17) 0.6484(21) 0.099(10) Uiso 1 d . . C10 C 0.1676(2) 0.26270(13) 0.8436(2) 0.0525(6) Uani 1 d . . H10A H 0.1889(15) 0.2181(12) 0.8824(15) 0.049(6) Uiso 1 d . . H10B H 0.1057(18) 0.2525(12) 0.7964(17) 0.058(7) Uiso 1 d . . C11 C 0.2658(2) 0.44529(11) 0.84795(15) 0.0410(5) Uani 1 d . . C12 C 0.2904(2) 0.49759(14) 0.7734(2) 0.0621(7) Uani 1 d . . H12 H 0.2623(17) 0.4924(12) 0.7091(18) 0.059(7) Uiso 1 d . . C13 C 0.3490(2) 0.5590(2) 0.7976(2) 0.0732(8) Uani 1 d . . H13 H 0.3617(20) 0.5943(15) 0.7492(20) 0.079(8) Uiso 1 d . . C14 C 0.3865(2) 0.57163(13) 0.8964(2) 0.0559(6) Uani 1 d . . C15 C 0.4501(3) 0.6398(2) 0.9229(4) 0.0857(10) Uani 1 d . . H15A H 0.4838(32) 0.6372(21) 0.9839(32) 0.138(16) Uiso 1 d . . H15B H 0.4054(39) 0.6814(30) 0.9308(37) 0.188(22) Uiso 1 d . . H15C H 0.5020(44) 0.6441(31) 0.8818(46) 0.206(25) Uiso 1 d . . C16 C 0.3621(2) 0.52040(13) 0.9705(2) 0.0541(6) Uani 1 d . . H16 H 0.3892(17) 0.5292(12) 1.0424(18) 0.059(6) Uiso 1 d . . C17 C 0.3024(2) 0.45907(13) 0.9476(2) 0.0503(6) Uani 1 d . . H17 H 0.2880(16) 0.4260(12) 0.9987(16) 0.050(6) Uiso 1 d . . O18 O 0.07144(13) 0.39727(9) 1.08786(11) 0.0603(5) Uani 1 d . . OW O 0.0000 0.51769(12) 0.7500 0.0502(6) Uani 1 d S . HO6 H 0.0929(21) 0.4355(15) 0.7544(18) 0.076(9) Uiso 1 d . . HW H -0.0261(23) 0.5467(16) 0.7990(20) 0.099(10) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.052(2) 0.096(2) 0.053(2) -0.013(2) 0.0043(14) 0.009(2) C2 0.0510(14) 0.0448(12) 0.0420(13) 0.0028(9) 0.0047(10) -0.0032(10) N3 0.0417(11) 0.0588(12) 0.0375(11) -0.0028(8) 0.0020(9) -0.0041(9) C4 0.0415(13) 0.0468(13) 0.0388(12) 0.0008(9) 0.0003(9) -0.0020(10) C5 0.0394(12) 0.0448(12) 0.0344(11) 0.0041(8) -0.0016(9) 0.0012(9) O6 0.0489(10) 0.0514(10) 0.0395(8) -0.0001(6) -0.0061(7) 0.0042(8) C7 0.0485(14) 0.0469(13) 0.0471(13) 0.0002(9) 0.0057(10) 0.0053(11) C8 0.057(2) 0.057(2) 0.076(2) 0.0065(14) 0.0050(14) 0.0151(15) C9 0.085(2) 0.067(2) 0.056(2) -0.0110(13) 0.016(2) 0.010(2) C10 0.062(2) 0.0409(13) 0.0551(14) 0.0018(11) 0.0027(13) -0.0001(12) C11 0.0358(12) 0.0438(12) 0.0436(12) 0.0041(9) 0.0027(9) 0.0018(9) C12 0.072(2) 0.069(2) 0.0455(15) 0.0069(11) -0.0018(12) -0.0191(14) C13 0.087(2) 0.068(2) 0.064(2) 0.0188(14) 0.0025(14) -0.030(2) C14 0.0412(13) 0.0546(15) 0.072(2) 0.0002(12) 0.0030(11) -0.0089(11) C15 0.074(2) 0.074(2) 0.109(3) 0.001(2) -0.005(2) -0.033(2) C16 0.0493(15) 0.059(2) 0.0537(15) -0.0016(11) -0.0062(11) -0.0078(12) C17 0.0526(15) 0.0528(15) 0.0454(14) 0.0110(10) -0.0032(10) -0.0062(12) O18 0.0610(11) 0.0762(12) 0.0434(9) -0.0118(7) -0.0052(8) 0.0063(8) OW 0.063(2) 0.0467(13) 0.0404(13) 0.000 -0.0019(11) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.490(4) . ? C2 O18 1.235(2) . ? C2 N3 1.345(3) . ? N3 C4 1.434(3) . ? C4 C10 1.541(3) . ? C4 C5 1.553(3) . ? C5 O6 1.430(2) . ? C5 C11 1.506(3) . ? C5 C7 1.572(3) . ? C7 C9 1.521(3) . ? C7 C8 1.525(3) . ? C7 C10 1.544(3) . ? C11 C17 1.388(3) . ? C11 C12 1.388(3) . ? C12 C13 1.376(4) . ? C13 C14 1.379(3) . ? C14 C16 1.370(3) . ? C14 C15 1.515(4) . ? C16 C17 1.378(3) . ? 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 O18 C2 N3 121.6(2) . . ? O18 C2 C1 121.8(2) . . ? N3 C2 C1 116.6(2) . . ? C2 N3 C4 123.9(2) . . ? N3 C4 C10 119.8(2) . . ? N3 C4 C5 117.7(2) . . ? C10 C4 C5 88.3(2) . . ? O6 C5 C11 110.7(2) . . ? O6 C5 C4 108.6(2) . . ? C11 C5 C4 120.4(2) . . ? O6 C5 C7 106.92(15) . . ? C11 C5 C7 120.3(2) . . ? C4 C5 C7 87.41(14) . . ? C9 C7 C8 110.2(2) . . ? C9 C7 C10 116.9(2) . . ? C8 C7 C10 111.8(2) . . ? C9 C7 C5 116.8(2) . . ? C8 C7 C5 112.1(2) . . ? C10 C7 C5 87.5(2) . . ? C4 C10 C7 88.9(2) . . ? C17 C11 C12 116.4(2) . . ? C17 C11 C5 123.0(2) . . ? C12 C11 C5 120.7(2) . . ? C13 C12 C11 121.3(2) . . ? C12 C13 C14 121.9(2) . . ? C16 C14 C13 117.0(2) . . ? C16 C14 C15 121.2(3) . . ? C13 C14 C15 121.7(3) . . ? C14 C16 C17 121.7(2) . . ? C16 C17 C11 121.7(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O18 C2 N3 C4 -4.4(3) . . . . ? C1 C2 N3 C4 175.3(2) . . . . ? C2 N3 C4 C10 144.1(2) . . . . ? C2 N3 C4 C5 -110.7(2) . . . . ? N3 C4 C5 O6 -37.0(2) . . . . ? C10 C4 C5 O6 86.1(2) . . . . ? N3 C4 C5 C11 92.0(2) . . . . ? C10 C4 C5 C11 -144.9(2) . . . . ? N3 C4 C5 C7 -144.0(2) . . . . ? C10 C4 C5 C7 -20.9(2) . . . . ? O6 C5 C7 C9 31.3(3) . . . . ? C11 C5 C7 C9 -96.0(3) . . . . ? C4 C5 C7 C9 139.9(2) . . . . ? O6 C5 C7 C8 159.8(2) . . . . ? C11 C5 C7 C8 32.5(3) . . . . ? C4 C5 C7 C8 -91.6(2) . . . . ? O6 C5 C7 C10 -87.7(2) . . . . ? C11 C5 C7 C10 145.0(2) . . . . ? C4 C5 C7 C10 20.9(2) . . . . ? N3 C4 C10 C7 142.6(2) . . . . ? C5 C4 C10 C7 21.3(2) . . . . ? C9 C7 C10 C4 -140.0(2) . . . . ? C8 C7 C10 C4 91.8(2) . . . . ? C5 C7 C10 C4 -21.1(2) . . . . ? O6 C5 C11 C17 147.3(2) . . . . ? C4 C5 C11 C17 19.2(3) . . . . ? C7 C5 C11 C17 -87.1(2) . . . . ? O6 C5 C11 C12 -32.2(3) . . . . ? C4 C5 C11 C12 -160.3(2) . . . . ? C7 C5 C11 C12 93.4(2) . . . . ? C17 C11 C12 C13 0.8(4) . . . . ? C5 C11 C12 C13 -179.7(2) . . . . ? C11 C12 C13 C14 0.3(5) . . . . ? C12 C13 C14 C16 -0.6(4) . . . . ? C12 C13 C14 C15 -179.4(3) . . . . ? C13 C14 C16 C17 -0.2(4) . . . . ? C15 C14 C16 C17 178.5(3) . . . . ? C14 C16 C17 C11 1.4(4) . . . . ? C12 C11 C17 C16 -1.6(3) . . . . ? C5 C11 C17 C16 178.9(2) . . . . ? _refine_diff_density_max .170 _refine_diff_density_min -.154 _refine_diff_density_rms .036 #===END data_2c _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C14 H19 N O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H19 N O2' _chemical_formula_weight 233.30 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .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 'P 21/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' _cell_length_a 7.459(1) _cell_length_b 11.632(2) _cell_length_c 15.652(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.67(2) _cell_angle_gamma 90.00 _cell_volume 1324.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method ? _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'nonius kappa-ccd diffractometer' _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2478 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0612 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2331 _reflns_number_observed 1202 _reflns_observed_criterion 2sigma(I) _computing_data_collection 'nonius collect' _computing_cell_refinement 'nonius denzo' _computing_data_reduction 'nonius denzo' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'xtal' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 135 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[s^2^(Fo^2^)+( 0.0467P)^2^+0.5079P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2196 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1410 _refine_ls_R_factor_obs 0.0638 _refine_ls_wR_factor_all 0.1719 _refine_ls_wR_factor_obs 0.1189 _refine_ls_goodness_of_fit_all 1.111 _refine_ls_goodness_of_fit_obs 1.183 _refine_ls_restrained_S_all 1.171 _refine_ls_restrained_S_obs 1.183 _refine_ls_shift/esd_max 0.537 _refine_ls_shift/esd_mean 0.059 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.0124(4) 0.0025(3) 0.2124(2) 0.0486(9) Uani 1 d . . C2 C 0.0134(6) 0.0975(4) 0.1434(3) 0.0677(12) Uani 1 d . . C3 C -0.1744(6) 0.0529(4) 0.0904(3) 0.0716(12) Uani 1 d . . C4 C -0.3187(11) 0.1397(6) 0.0493(6) 0.112(2) Uani 1 d . . C5 C -0.1969(4) -0.0068(3) 0.1756(3) 0.0501(10) Uani 1 d . . N6 N -0.2734(4) -0.1206(3) 0.1735(2) 0.0545(9) Uani 1 d . . C7 C -0.4424(5) -0.1446(3) 0.1829(2) 0.0522(10) Uani 1 d . . O8 O -0.5481(3) -0.0668(2) 0.1928(2) 0.0767(9) Uani 1 d . . O9 O 0.0906(4) -0.1002(2) 0.1878(2) 0.0637(8) Uani 1 d . . C10 C 0.0799(4) 0.0302(3) 0.3077(3) 0.0469(9) Uani 1 d . . C11 C 0.0202(5) 0.1292(3) 0.3434(3) 0.0517(10) Uani 1 d . . C12 C 0.0799(5) 0.1552(3) 0.4313(3) 0.0565(10) Uani 1 d . . C13 C 0.2006(5) 0.0825(4) 0.4876(3) 0.0591(11) Uani 1 d . . C14 C 0.2660(9) 0.1126(7) 0.5828(4) 0.086(2) Uani 1 d . . C15 C 0.2565(5) -0.0149(4) 0.4511(3) 0.0606(12) Uani 1 d . . C16 C 0.1993(5) -0.0411(4) 0.3641(3) 0.0591(11) Uani 1 d . . C17 C -0.4926(7) -0.2696(4) 0.1823(5) 0.0722(14) Uani 1 d . . H2A H -0.0084(46) 0.1773(32) 0.1695(23) 0.064(11) Uiso 1 d . . H2B H 0.1132(56) 0.0993(37) 0.1164(26) 0.089(15) Uiso 1 d . . H3 H -0.1515(47) -0.0064(32) 0.0448(24) 0.066(11) Uiso 1 d . . H4A H -0.4379(68) 0.1067(42) 0.0280(31) 0.107(18) Uiso 1 d . . H4B H -0.2942(104) 0.1748(67) 0.0027(51) 0.212(39) Uiso 1 d . . H4C H -0.3477(91) 0.1918(65) 0.1052(48) 0.198(35) Uiso 1 d . . H5 H -0.2614(33) 0.0434(22) 0.2060(16) 0.021(7) Uiso 1 d . . HN6 H -0.2007(49) -0.1782(33) 0.1673(23) 0.063(12) Uiso 1 d . . HO9 H 0.2120(70) -0.0909(42) 0.1911(29) 0.117(18) Uiso 1 d . . H11 H -0.0628(47) 0.1858(32) 0.3040(23) 0.071(12) Uiso 1 d . . H12 H 0.0407(35) 0.2202(24) 0.4587(17) 0.026(8) Uiso 1 d . . H14A H 0.1792(92) 0.1265(64) 0.6081(43) 0.181(32) Uiso 1 d . . H14B H 0.3330(80) 0.1852(51) 0.5868(36) 0.134(24) Uiso 1 d . . H14C H 0.3587(76) 0.0738(48) 0.6101(35) 0.122(24) Uiso 1 d . . H15 H 0.3276(46) -0.0559(28) 0.4866(22) 0.047(11) Uiso 1 d . . H16 H 0.2468(50) -0.1154(35) 0.3375(23) 0.078(12) Uiso 1 d . . H17A H -0.6159(68) -0.2788(39) 0.1600(29) 0.103(16) Uiso 1 d . . H17B H -0.4935(75) -0.2908(48) 0.2401(40) 0.139(24) Uiso 1 d . . H17C H -0.4216(83) -0.3164(52) 0.1563(38) 0.153(25) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(2) 0.036(2) 0.076(3) -0.004(2) 0.018(2) -0.004(2) C2 0.067(3) 0.063(3) 0.078(3) -0.003(2) 0.026(2) -0.019(2) C3 0.079(3) 0.060(3) 0.074(3) -0.001(3) 0.012(2) -0.015(2) C4 0.109(5) 0.087(4) 0.112(5) 0.030(4) -0.036(4) -0.008(4) C5 0.038(2) 0.040(2) 0.074(3) -0.012(2) 0.016(2) -0.001(2) N6 0.031(2) 0.044(2) 0.090(3) -0.006(2) 0.016(2) -0.0022(14) C7 0.035(2) 0.055(2) 0.067(3) -0.004(2) 0.012(2) -0.005(2) O8 0.0386(14) 0.075(2) 0.121(2) -0.020(2) 0.0284(15) 0.0012(14) O9 0.0383(14) 0.055(2) 0.102(2) -0.024(2) 0.0250(14) -0.0046(12) C10 0.029(2) 0.042(2) 0.071(3) -0.001(2) 0.013(2) -0.007(2) C11 0.045(2) 0.039(2) 0.074(3) 0.001(2) 0.019(2) 0.001(2) C12 0.055(2) 0.048(2) 0.073(3) -0.008(2) 0.026(2) -0.003(2) C13 0.046(2) 0.063(3) 0.069(3) 0.003(2) 0.015(2) -0.009(2) C14 0.075(4) 0.113(5) 0.073(4) -0.008(3) 0.019(3) -0.003(4) C15 0.045(2) 0.061(3) 0.073(3) 0.009(3) 0.007(2) 0.007(2) C16 0.048(2) 0.046(2) 0.084(3) 0.002(2) 0.017(2) 0.005(2) C17 0.046(3) 0.064(3) 0.109(4) 0.001(3) 0.023(3) -0.016(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 C1 O9 1.420(4) . ? C1 C10 1.501(5) . ? C1 C5 1.544(4) . ? C1 C2 1.547(5) . ? C2 C3 1.552(6) . ? C3 C4 1.513(7) . ? C3 C5 1.544(5) . ? C5 N6 1.439(4) . ? N6 C7 1.331(4) . ? C7 O8 1.231(4) . ? C7 C17 1.501(6) . ? C10 C16 1.384(5) . ? C10 C11 1.394(5) . ? C11 C12 1.382(5) . ? C12 C13 1.398(5) . ? C13 C15 1.374(5) . ? C13 C14 1.504(7) . ? C15 C16 1.369(6) . ? 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 O9 C1 C10 112.5(3) . . ? O9 C1 C5 106.4(3) . . ? C10 C1 C5 118.5(3) . . ? O9 C1 C2 110.2(3) . . ? C10 C1 C2 119.3(3) . . ? C5 C1 C2 87.1(3) . . ? C3 C2 C1 89.5(3) . . ? C4 C3 C2 118.6(4) . . ? C4 C3 C5 117.8(5) . . ? C2 C3 C5 86.9(3) . . ? N6 C5 C1 115.8(3) . . ? N6 C5 C3 120.8(3) . . ? C1 C5 C3 89.9(3) . . ? C7 N6 C5 124.8(3) . . ? O8 C7 N6 120.5(3) . . ? O8 C7 C17 123.1(4) . . ? N6 C7 C17 116.3(4) . . ? C16 C10 C11 117.2(4) . . ? C16 C10 C1 122.3(3) . . ? C11 C10 C1 120.6(3) . . ? C10 C11 C12 121.2(4) . . ? C11 C12 C13 121.1(4) . . ? C15 C13 C12 116.7(4) . . ? C15 C13 C14 122.8(5) . . ? C12 C13 C14 120.5(5) . . ? C13 C15 C16 122.7(4) . . ? C10 C16 C15 121.2(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O9 C1 C2 C3 87.1(4) . . . . ? C10 C1 C2 C3 -140.5(3) . . . . ? C5 C1 C2 C3 -19.2(3) . . . . ? C1 C2 C3 C4 139.3(6) . . . . ? C1 C2 C3 C5 19.2(3) . . . . ? O9 C1 C5 N6 33.7(4) . . . . ? C10 C1 C5 N6 -94.1(4) . . . . ? C2 C1 C5 N6 143.9(4) . . . . ? O9 C1 C5 C3 -90.9(3) . . . . ? C10 C1 C5 C3 141.3(3) . . . . ? C2 C1 C5 C3 19.3(3) . . . . ? C4 C3 C5 N6 99.5(5) . . . . ? C2 C3 C5 N6 -139.7(4) . . . . ? C4 C3 C5 C1 -140.1(4) . . . . ? C2 C3 C5 C1 -19.3(3) . . . . ? C1 C5 N6 C7 148.3(3) . . . . ? C3 C5 N6 C7 -105.0(4) . . . . ? C5 N6 C7 O8 1.4(6) . . . . ? C5 N6 C7 C17 -177.6(4) . . . . ? O9 C1 C10 C16 -2.5(4) . . . . ? C5 C1 C10 C16 122.4(4) . . . . ? C2 C1 C10 C16 -133.9(4) . . . . ? O9 C1 C10 C11 178.9(3) . . . . ? C5 C1 C10 C11 -56.2(4) . . . . ? C2 C1 C10 C11 47.5(4) . . . . ? C16 C10 C11 C12 0.7(5) . . . . ? C1 C10 C11 C12 179.4(3) . . . . ? C10 C11 C12 C13 -0.7(5) . . . . ? C11 C12 C13 C15 0.2(5) . . . . ? C11 C12 C13 C14 179.3(4) . . . . ? C12 C13 C15 C16 0.3(6) . . . . ? C14 C13 C15 C16 -178.8(4) . . . . ? C11 C10 C16 C15 -0.2(5) . . . . ? C1 C10 C16 C15 -178.9(3) . . . . ? C13 C15 C16 C10 -0.3(6) . . . . ? _refine_diff_density_max .181 _refine_diff_density_min -.184 _refine_diff_density_rms .043 #===END data_2d _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C15 H21 N O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H21 N O2' _chemical_formula_weight 247.33 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.546(1) _cell_length_b 11.848(1) _cell_length_c 15.712(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1404.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method ? _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'nonius kappa-ccd diffractometer' _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3096 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0618 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.10 _reflns_number_total 3096 _reflns_number_observed 1942 _reflns_observed_criterion 2sigma(I) _computing_data_collection 'nonius collect' _computing_cell_refinement 'nonius denzo' _computing_data_reduction 'nonius denzo' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'xtal' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 43 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[s^2^(Fo^2^)+( 0.0605P)^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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0201(35) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.96(175) _refine_ls_number_reflns 3053 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1001 _refine_ls_R_factor_obs 0.0502 _refine_ls_wR_factor_all 0.1158 _refine_ls_wR_factor_obs 0.0990 _refine_ls_goodness_of_fit_all 1.011 _refine_ls_goodness_of_fit_obs 1.133 _refine_ls_restrained_S_all 1.025 _refine_ls_restrained_S_obs 1.133 _refine_ls_shift/esd_max -1.823 _refine_ls_shift/esd_mean 0.160 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.0939(2) 0.34652(11) 0.68425(11) 0.0458(4) Uani 1 d . . N2 N -0.2595(2) 0.3745(2) 0.68040(15) 0.0491(6) Uani 1 d . . C3 C 0.0390(2) 0.2267(2) 0.80710(15) 0.0379(5) Uani 1 d . . O4 O -0.5438(2) 0.3268(2) 0.6946(2) 0.0784(7) Uani 1 d . . C5 C -0.0066(3) 0.1247(2) 0.8454(2) 0.0432(6) Uani 1 d . . C6 C 0.0044(3) 0.2486(2) 0.71413(14) 0.0381(5) Uani 1 d . . C7 C -0.1905(3) 0.2610(2) 0.6845(2) 0.0417(6) Uani 1 d . . C8 C 0.0893(3) 0.1896(2) 0.9835(2) 0.0509(7) Uani 1 d . . C9 C -0.4315(3) 0.3999(2) 0.6838(2) 0.0521(6) Uani 1 d . . C10 C 0.1330(4) 0.2909(2) 0.9452(2) 0.0578(8) Uani 1 d . . C11 C 0.1105(3) 0.3088(2) 0.8598(2) 0.0516(7) Uani 1 d . . C12 C -0.1444(3) 0.1981(2) 0.6023(2) 0.0493(6) Uani 1 d . . C13 C 0.0189(3) 0.1068(2) 0.9310(2) 0.0488(6) Uani 1 d . . C14 C 0.0182(3) 0.1500(2) 0.6488(2) 0.0468(6) Uani 1 d . . C15 C 0.1891(4) 0.1320(3) 0.5997(2) 0.0676(8) Uani 1 d . . C16 C 0.1108(6) 0.1714(4) 1.0776(2) 0.0732(9) Uani 1 d . . C17 C -0.2785(5) 0.1170(3) 0.5644(3) 0.0728(9) Uani 1 d . . C18 C -0.4774(5) 0.5226(3) 0.6740(3) 0.0789(11) Uani 1 d . . H1 H -0.2684(31) 0.2195(17) 0.7195(14) 0.038(6) Uiso 1 d . . H2 H -0.0577(30) 0.0690(19) 0.8097(14) 0.046(6) Uiso 1 d . . H3 H -0.0185(31) 0.0813(20) 0.6764(14) 0.050(7) Uiso 1 d . . H4 H 0.2812(59) 0.1045(30) 0.6388(25) 0.113(13) Uiso 1 d . . H5 H -0.0045(31) 0.0346(21) 0.9551(15) 0.047(7) Uiso 1 d . . H6 H 0.2308(47) 0.2032(29) 0.5797(23) 0.092(11) Uiso 1 d . . H7 H 0.1070(67) 0.1025(41) 1.0888(28) 0.145(19) Uiso 1 d . . H8 H -0.1154(35) 0.2533(20) 0.5591(16) 0.056(7) Uiso 1 d . . H9 H 0.1465(33) 0.3790(22) 0.8362(15) 0.058(7) Uiso 1 d . . H10 H 0.2241(89) 0.1695(45) 1.0964(41) 0.180(24) Uiso 1 d . . H11 H -0.2194(64) 0.0839(34) 0.5142(29) 0.135(17) Uiso 1 d . . H12 H 0.1674(54) 0.0716(31) 0.5565(26) 0.115(13) Uiso 1 d . . H13 H -0.1788(34) 0.4272(19) 0.6703(14) 0.046(7) Uiso 1 d . . H14 H 0.1856(40) 0.3468(22) 0.9802(18) 0.066(8) Uiso 1 d . . H15 H -0.3125(44) 0.0568(28) 0.6103(22) 0.092(11) Uiso 1 d . . H16 H -0.3779(48) 0.1551(24) 0.5447(20) 0.081(10) Uiso 1 d . . H17 H -0.5599(74) 0.5294(43) 0.6301(34) 0.159(22) Uiso 1 d . . H18 H -0.3819(64) 0.5704(34) 0.6706(26) 0.128(16) Uiso 1 d . . H19 H 0.0666(84) 0.2414(51) 1.1187(34) 0.209(23) Uiso 1 d . . H20 H 0.2095(44) 0.3356(22) 0.6889(21) 0.077(9) Uiso 1 d . . H24 H -0.5759(58) 0.5357(33) 0.7040(29) 0.132(15) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0261(8) 0.0403(8) 0.0710(12) 0.0139(8) 0.0019(9) -0.0012(7) N2 0.0259(10) 0.0397(11) 0.082(2) 0.0072(10) 0.0022(10) 0.0011(8) C3 0.0220(9) 0.0337(11) 0.058(2) -0.0005(10) 0.0004(10) 0.0005(8) O4 0.0270(9) 0.0763(12) 0.132(2) 0.0151(13) 0.0004(11) -0.0009(9) C5 0.0345(12) 0.0355(13) 0.060(2) -0.0033(11) 0.0031(11) -0.0041(10) C6 0.0261(10) 0.0329(11) 0.0553(15) 0.0047(10) -0.0013(10) -0.0009(9) C7 0.0273(11) 0.0381(12) 0.060(2) 0.0034(12) -0.0005(12) -0.0018(9) C8 0.0363(13) 0.057(2) 0.059(2) 0.0001(12) -0.0031(13) 0.0039(12) C9 0.0285(12) 0.0583(13) 0.069(2) 0.0007(13) -0.0038(13) 0.0038(11) C10 0.059(2) 0.050(2) 0.065(2) -0.0053(14) -0.0116(15) -0.0108(12) C11 0.049(2) 0.0405(14) 0.065(2) 0.0036(12) -0.0084(14) -0.0101(11) C12 0.0413(14) 0.0476(14) 0.059(2) 0.0028(13) -0.0067(13) 0.0012(10) C13 0.0461(14) 0.0433(14) 0.057(2) 0.0058(12) 0.0056(13) -0.0010(11) C14 0.0436(13) 0.0407(13) 0.056(2) 0.0027(11) -0.0009(12) 0.0052(10) C15 0.055(2) 0.076(2) 0.071(2) -0.008(2) 0.006(2) 0.019(2) C16 0.081(3) 0.080(2) 0.059(2) 0.009(2) -0.013(2) -0.001(2) C17 0.065(2) 0.070(2) 0.083(3) -0.014(2) -0.026(2) -0.004(2) C18 0.046(2) 0.063(2) 0.128(4) 0.000(2) -0.007(2) 0.0203(15) _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 C6 1.422(3) . ? N2 C9 1.334(3) . ? N2 C7 1.443(3) . ? C3 C11 1.387(3) . ? C3 C5 1.393(3) . ? C3 C6 1.506(3) . ? O4 C9 1.224(3) . ? C5 C13 1.374(3) . ? C6 C7 1.549(3) . ? C6 C14 1.558(3) . ? C7 C12 1.531(4) . ? C8 C13 1.388(3) . ? C8 C10 1.383(3) . ? C8 C16 1.504(4) . ? C9 C18 1.502(4) . ? C10 C11 1.369(4) . ? C12 C17 1.517(4) . ? C12 C14 1.538(3) . ? C14 C15 1.518(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N2 C7 124.1(2) . . ? C11 C3 C5 116.5(2) . . ? C11 C3 C6 121.7(2) . . ? C5 C3 C6 121.7(2) . . ? C13 C5 C3 121.4(2) . . ? O1 C6 C3 112.2(2) . . ? O1 C6 C7 105.9(2) . . ? C3 C6 C7 118.1(2) . . ? O1 C6 C14 111.3(2) . . ? C3 C6 C14 119.8(2) . . ? C7 C6 C14 86.4(2) . . ? N2 C7 C6 116.4(2) . . ? N2 C7 C12 119.8(2) . . ? C6 C7 C12 89.5(2) . . ? C13 C8 C10 116.5(3) . . ? C13 C8 C16 121.7(3) . . ? C10 C8 C16 121.8(3) . . ? O4 C9 N2 121.3(2) . . ? O4 C9 C18 122.7(2) . . ? N2 C9 C18 116.1(2) . . ? C11 C10 C8 122.1(3) . . ? C10 C11 C3 121.7(2) . . ? C17 C12 C14 118.9(2) . . ? C17 C12 C7 119.2(3) . . ? C14 C12 C7 87.7(2) . . ? C5 C13 C8 121.7(2) . . ? C12 C14 C15 119.2(2) . . ? C12 C14 C6 88.9(2) . . ? C15 C14 C6 119.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C3 C5 C13 -0.3(3) . . . . ? C6 C3 C5 C13 -177.4(2) . . . . ? C11 C3 C6 O1 15.5(3) . . . . ? C5 C3 C6 O1 -167.4(2) . . . . ? C11 C3 C6 C7 -108.2(2) . . . . ? C5 C3 C6 C7 68.9(3) . . . . ? C11 C3 C6 C14 148.9(2) . . . . ? C5 C3 C6 C14 -34.1(3) . . . . ? C9 N2 C7 C6 -157.3(2) . . . . ? C9 N2 C7 C12 96.9(3) . . . . ? O1 C6 C7 N2 -32.6(3) . . . . ? C3 C6 C7 N2 94.1(3) . . . . ? C14 C6 C7 N2 -143.7(2) . . . . ? O1 C6 C7 C12 90.8(2) . . . . ? C3 C6 C7 C12 -142.4(2) . . . . ? C14 C6 C7 C12 -20.3(2) . . . . ? C7 N2 C9 O4 3.3(4) . . . . ? C7 N2 C9 C18 -177.0(3) . . . . ? C13 C8 C10 C11 -0.8(4) . . . . ? C16 C8 C10 C11 -178.7(3) . . . . ? C8 C10 C11 C3 1.3(4) . . . . ? C5 C3 C11 C10 -0.8(4) . . . . ? C6 C3 C11 C10 176.4(2) . . . . ? N2 C7 C12 C17 -96.7(3) . . . . ? C6 C7 C12 C17 142.8(2) . . . . ? N2 C7 C12 C14 141.1(2) . . . . ? C6 C7 C12 C14 20.6(2) . . . . ? C3 C5 C13 C8 0.8(4) . . . . ? C10 C8 C13 C5 -0.2(4) . . . . ? C16 C8 C13 C5 177.6(3) . . . . ? C17 C12 C14 C15 93.1(4) . . . . ? C7 C12 C14 C15 -144.4(3) . . . . ? C17 C12 C14 C6 -142.9(3) . . . . ? C7 C12 C14 C6 -20.5(2) . . . . ? O1 C6 C14 C12 -85.4(2) . . . . ? C3 C6 C14 C12 140.8(2) . . . . ? C7 C6 C14 C12 20.2(2) . . . . ? O1 C6 C14 C15 38.1(3) . . . . ? C3 C6 C14 C15 -95.7(3) . . . . ? C7 C6 C14 C15 143.8(3) . . . . ? _refine_diff_density_max .145 _refine_diff_density_min -.124 _refine_diff_density_rms .032 #===END