#==================== data_general _publ_contact_author ; Professor Jeffrey Aub\'e Department of Medicinal Chemistry -- University of Kansas Malott Hall 1251 Wescoe Hall Dr, Rm 4070 Lawrence, KS 66045-7582 USA ; _publ_contact_author_email jaube@ku.edu _publ_contact_author_fax 1(785)8645326 _publ_contact_author_phone 1(785)8644496 _publ_requested_journal 'J.Org. Chem.' loop_ _publ_author_name _publ_author_address 'Huh, Chan Woo' ; Department of Medicinal Chemistry -- University of Kansas Malott Hall 1251 Wescoe Hall Dr, Rm 4070 Lawrence, KS 66045-7582 USA ; 'Somal, Gagandeep K.' ; Department of Medicinal Chemistry -- University of Kansas Malott Hall 1251 Wescoe Hall Dr, Rm 4070 Lawrence, KS 66045-7582 USA ; 'Katz, Christopher E.' ; Department of Medicinal Chemistry -- University of Kansas Malott Hall 1251 Wescoe Hall Dr, Rm 4070 Lawrence, KS 66045-7582 USA ; 'Pei, Mike' ; Department of Medicinal Chemistry -- University of Kansas Malott Hall 1251 Wescoe Hall Dr, Rm 4070 Lawrence, KS 66045-7582 USA ; 'Zeng, Yibin' ; Department of Medicinal Chemistry -- University of Kansas Malott Hall 1251 Wescoe Hall Dr, Rm 4070 Lawrence, KS 66045-7582 USA ; 'Douglas, Justin T.' ; Department of Medicinal Chemistry -- University of Kansas Malott Hall 1251 Wescoe Hall Dr, Rm 4070 Lawrence, KS 66045-7582 USA ; 'Aub\'e, Jeffrey' ; Department of Medicinal Chemistry -- University of Kansas Malott Hall 1251 Wescoe Hall Dr, Rm 4070 Lawrence, KS 66045-7582 USA ; _publ_section_title ; article title here 'One Pot Synthesis of Lactams Using Domino Reactions: Combination of Schmidt Reaction with Sakurai and Aldol Reactions' ; _publ_section_references ; Bruker (1998) SMART and SAINT, Bruker AXS, Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (2000) SADABS, University of G\"ottingen, Germany Sheldrick, G. M. (1997) SHELXTL, Bruker AXS, Inc., Madison, Wisconsin, USA. ; _publ_section_acknowledgements ; The authors wish to thank the National Science Foundation (CHE-0079282) and the University of Kansas for funds to acquire the diffractometer and computers used in this work. ; data_Cmpd_19_major_(k18g) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H27 N O2' _chemical_formula_weight 253.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.2331(10) _cell_length_b 14.3356(12) _cell_length_c 9.0220(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.670(2) _cell_angle_gamma 90.00 _cell_volume 1452.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3306 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 28.90 _exptl_crystal_description 'square plate' _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.912 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 11009 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 30.53 _reflns_number_total 4300 _reflns_number_gt 3351 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections except those that were flagged by the user for being in the beamstop. 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^)+(0.0799P)^2^+0.0836P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4300 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1399 _refine_ls_wR_factor_gt 0.1312 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.49955(7) 0.57248(5) 0.27651(9) 0.01864(19) Uani 1 1 d . . . O2 O 0.38484(8) 0.20121(5) 0.05433(9) 0.0206(2) Uani 1 1 d . . . H2O H 0.4208 0.1612 0.1062 0.031 Uiso 1 1 calc R . . N N 0.45851(8) 0.42335(6) 0.21747(10) 0.0138(2) Uani 1 1 d . . . C1 C 0.52516(9) 0.48821(7) 0.28578(12) 0.0146(2) Uani 1 1 d . . . C2 C 0.63435(10) 0.45586(8) 0.37016(13) 0.0171(2) Uani 1 1 d . . . H2A H 0.6120 0.4048 0.4383 0.021 Uiso 1 1 calc R . . H2B H 0.6659 0.5081 0.4307 0.021 Uiso 1 1 calc R . . C3 C 0.73199(10) 0.42114(8) 0.26532(13) 0.0196(2) Uani 1 1 d . . . H3A H 0.7354 0.4636 0.1789 0.023 Uiso 1 1 calc R . . H3B H 0.8097 0.4248 0.3178 0.023 Uiso 1 1 calc R . . C4 C 0.71403(10) 0.32157(8) 0.20927(14) 0.0211(3) Uani 1 1 d . . . H4A H 0.7820 0.3054 0.1453 0.025 Uiso 1 1 calc R . . H4B H 0.7168 0.2790 0.2957 0.025 Uiso 1 1 calc R . . C5 C 0.59925(10) 0.30251(8) 0.12252(13) 0.0182(2) Uani 1 1 d . . . H5A H 0.5985 0.2363 0.0913 0.022 Uiso 1 1 calc R . . H5B H 0.5986 0.3413 0.0317 0.022 Uiso 1 1 calc R . . C6 C 0.48634(10) 0.32254(7) 0.20965(12) 0.0140(2) Uani 1 1 d . . . H6A H 0.4951 0.2969 0.3123 0.017 Uiso 1 1 calc R . . C7 C 0.37126(10) 0.28405(7) 0.13708(13) 0.0158(2) Uani 1 1 d . . . H7A H 0.3106 0.2735 0.2156 0.019 Uiso 1 1 calc R . . C8 C 0.32903(10) 0.36301(7) 0.03566(12) 0.0164(2) Uani 1 1 d . . . H8A H 0.3743 0.3637 -0.0579 0.020 Uiso 1 1 calc R . . H8B H 0.2431 0.3569 0.0120 0.020 Uiso 1 1 calc R . . C9 C 0.35367(10) 0.45084(7) 0.12679(12) 0.0140(2) Uani 1 1 d . . . H9A H 0.3756 0.5033 0.0593 0.017 Uiso 1 1 calc R . . C10 C 0.24982(10) 0.48063(8) 0.22469(12) 0.0166(2) Uani 1 1 d . . . H10A H 0.2178 0.4251 0.2758 0.020 Uiso 1 1 calc R . . H10B H 0.2795 0.5245 0.3014 0.020 Uiso 1 1 calc R . . C11 C 0.14972(10) 0.52735(8) 0.13629(13) 0.0201(2) Uani 1 1 d . . . H11A H 0.1284 0.4872 0.0508 0.024 Uiso 1 1 calc R . . H11B H 0.1792 0.5873 0.0967 0.024 Uiso 1 1 calc R . . C12 C 0.03779(10) 0.54586(8) 0.22643(13) 0.0202(2) Uani 1 1 d . . . H12A H -0.0259 0.5682 0.1584 0.024 Uiso 1 1 calc R . . H12B H 0.0107 0.4862 0.2699 0.024 Uiso 1 1 calc R . . C13 C 0.05365(10) 0.61662(8) 0.35054(13) 0.0189(2) Uani 1 1 d . . . H13A H 0.0857 0.6751 0.3086 0.023 Uiso 1 1 calc R . . H13B H 0.1129 0.5924 0.4229 0.023 Uiso 1 1 calc R . . C14 C -0.06135(11) 0.63839(8) 0.43129(14) 0.0222(3) Uani 1 1 d . . . H14A H -0.1216 0.6605 0.3585 0.027 Uiso 1 1 calc R . . H14B H -0.0919 0.5804 0.4765 0.027 Uiso 1 1 calc R . . C15 C -0.04554(14) 0.71170(9) 0.55149(17) 0.0321(3) Uani 1 1 d . . . H15A H -0.1219 0.7226 0.6000 0.048 Uiso 1 1 calc R . . H15B H -0.0175 0.7700 0.5071 0.048 Uiso 1 1 calc R . . H15C H 0.0130 0.6898 0.6250 0.048 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 0.0212(4) 0.0140(4) 0.0206(4) -0.0021(3) -0.0003(3) 0.0000(3) O2 0.0292(5) 0.0129(4) 0.0197(4) -0.0020(3) -0.0026(3) 0.0012(3) N 0.0150(4) 0.0128(4) 0.0136(5) 0.0003(3) -0.0010(3) 0.0010(3) C1 0.0158(5) 0.0160(5) 0.0122(5) 0.0000(4) 0.0027(4) -0.0005(4) C2 0.0180(5) 0.0180(5) 0.0153(5) 0.0008(4) -0.0013(4) -0.0008(4) C3 0.0145(5) 0.0233(6) 0.0209(6) 0.0023(4) -0.0008(4) 0.0001(4) C4 0.0177(6) 0.0215(6) 0.0242(6) 0.0019(4) 0.0024(5) 0.0047(4) C5 0.0201(6) 0.0156(5) 0.0190(6) -0.0006(4) 0.0035(4) 0.0021(4) C6 0.0178(5) 0.0112(5) 0.0130(5) 0.0014(4) 0.0007(4) 0.0015(4) C7 0.0185(5) 0.0137(5) 0.0154(5) -0.0006(4) 0.0007(4) -0.0010(4) C8 0.0195(5) 0.0156(5) 0.0140(5) -0.0003(4) -0.0019(4) 0.0005(4) C9 0.0152(5) 0.0141(5) 0.0126(5) 0.0007(4) -0.0011(4) 0.0013(4) C10 0.0163(5) 0.0197(5) 0.0138(5) -0.0003(4) -0.0001(4) 0.0022(4) C11 0.0176(5) 0.0269(6) 0.0157(6) -0.0021(4) -0.0019(4) 0.0048(4) C12 0.0142(5) 0.0248(6) 0.0214(6) -0.0032(5) -0.0023(4) 0.0013(4) C13 0.0153(5) 0.0211(5) 0.0204(6) -0.0016(4) -0.0006(4) 0.0006(4) C14 0.0197(6) 0.0239(6) 0.0232(6) 0.0001(5) 0.0029(5) 0.0029(4) C15 0.0353(8) 0.0279(7) 0.0333(8) -0.0065(5) 0.0055(6) 0.0085(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 C1 1.2443(13) . ? O2 C7 1.4120(13) . ? O2 H2O 0.8400 . ? N C1 1.3395(14) . ? N C9 1.4795(14) . ? N C6 1.4805(13) . ? C1 C2 1.5090(16) . ? C2 C3 1.5395(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5269(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5251(17) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5271(15) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5441(16) . ? C6 H6A 1.0000 . ? C7 C8 1.5276(15) . ? C7 H7A 1.0000 . ? C8 C9 1.5273(15) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5322(14) . ? C9 H9A 1.0000 . ? C10 C11 1.5258(16) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5286(16) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.5198(16) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.5228(15) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5190(18) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 C7 O2 H2O 109.5 . . ? C1 N C9 120.43(9) . . ? C1 N C6 125.62(9) . . ? C9 N C6 113.63(8) . . ? O1 C1 N 121.03(10) . . ? O1 C1 C2 121.21(10) . . ? N C1 C2 117.73(10) . . ? C1 C2 C3 111.73(9) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 114.42(9) . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3B 108.7 . . ? C2 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C5 C4 C3 116.43(9) . . ? C5 C4 H4A 108.2 . . ? C3 C4 H4A 108.2 . . ? C5 C4 H4B 108.2 . . ? C3 C4 H4B 108.2 . . ? H4A C4 H4B 107.3 . . ? C4 C5 C6 113.85(9) . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? N C6 C5 112.65(8) . . ? N C6 C7 101.12(8) . . ? C5 C6 C7 114.25(9) . . ? N C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? O2 C7 C8 109.95(9) . . ? O2 C7 C6 115.44(9) . . ? C8 C7 C6 103.99(8) . . ? O2 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? C9 C8 C7 103.61(9) . . ? C9 C8 H8A 111.0 . . ? C7 C8 H8A 111.0 . . ? C9 C8 H8B 111.0 . . ? C7 C8 H8B 111.0 . . ? H8A C8 H8B 109.0 . . ? N C9 C8 102.49(8) . . ? N C9 C10 111.22(8) . . ? C8 C9 C10 113.93(9) . . ? N C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? C11 C10 C9 112.49(9) . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 113.82(10) . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 114.69(10) . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12A 108.6 . . ? C13 C12 H12B 108.6 . . ? C11 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C12 C13 C14 113.36(10) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C13 112.99(11) . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? 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 . . ? 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 C9 N C1 O1 1.12(15) . . . . ? C6 N C1 O1 174.19(9) . . . . ? C9 N C1 C2 -176.99(9) . . . . ? C6 N C1 C2 -3.91(15) . . . . ? O1 C1 C2 C3 -108.08(11) . . . . ? N C1 C2 C3 70.01(12) . . . . ? C1 C2 C3 C4 -80.73(12) . . . . ? C2 C3 C4 C5 59.41(13) . . . . ? C3 C4 C5 C6 -59.24(13) . . . . ? C1 N C6 C5 -64.75(14) . . . . ? C9 N C6 C5 108.74(10) . . . . ? C1 N C6 C7 172.87(10) . . . . ? C9 N C6 C7 -13.65(10) . . . . ? C4 C5 C6 N 77.87(12) . . . . ? C4 C5 C6 C7 -167.48(9) . . . . ? N C6 C7 O2 152.73(9) . . . . ? C5 C6 C7 O2 31.46(13) . . . . ? N C6 C7 C8 32.20(10) . . . . ? C5 C6 C7 C8 -89.07(10) . . . . ? O2 C7 C8 C9 -163.89(9) . . . . ? C6 C7 C8 C9 -39.73(10) . . . . ? C1 N C9 C8 163.53(9) . . . . ? C6 N C9 C8 -10.33(11) . . . . ? C1 N C9 C10 -74.35(12) . . . . ? C6 N C9 C10 111.80(10) . . . . ? C7 C8 C9 N 30.32(10) . . . . ? C7 C8 C9 C10 -89.94(11) . . . . ? N C9 C10 C11 168.65(9) . . . . ? C8 C9 C10 C11 -76.12(12) . . . . ? C9 C10 C11 C12 172.07(9) . . . . ? C10 C11 C12 C13 65.84(14) . . . . ? C11 C12 C13 C14 176.06(10) . . . . ? C12 C13 C14 C15 -177.96(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O1 0.84 1.88 2.7157(12) 179.5 2_645 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.484 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.065 data_Cmpd_23a_(04046) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H19 N O2' _chemical_formula_sum 'C12 H19 N O2' _chemical_formula_weight 209.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' 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 31.564(4) _cell_length_b 4.7098(6) _cell_length_c 15.1845(18) _cell_angle_alpha 90.00 _cell_angle_beta 101.074(3) _cell_angle_gamma 90.00 _cell_volume 2215.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3992 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 26.00 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9605 _exptl_absorpt_correction_T_max 0.9966 _exptl_absorpt_process_details 'SADABS (2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9068 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2181 _reflns_number_gt 1987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Hydrogens bound to carbons were located by geometry and refined by a riding model. The hydrogen bound to O(1) was located on a difference map and refined independently. ; _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^)+(0.0700P)^2^+1.6000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2181 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.17057(3) 0.65134(19) -0.01163(6) 0.0193(2) Uani 1 1 d . . . H1O H 0.1774(5) 0.661(4) -0.0646(12) 0.029(4) Uiso 1 1 d . . . O2 O 0.19064(3) 0.3982(2) 0.32427(6) 0.0242(2) Uani 1 1 d . . . N1 N 0.17602(3) 0.3820(2) 0.17339(6) 0.0162(2) Uani 1 1 d . . . C1 C 0.21648(4) 0.5311(3) 0.16776(8) 0.0172(3) Uani 1 1 d . . . H1A H 0.2391 0.4940 0.2214 0.021 Uiso 1 1 calc R . . H1B H 0.2119 0.7385 0.1609 0.021 Uiso 1 1 calc R . . C2 C 0.22824(4) 0.4012(3) 0.08397(8) 0.0187(3) Uani 1 1 d . . . H2A H 0.2479 0.5266 0.0581 0.022 Uiso 1 1 calc R . . H2B H 0.2419 0.2128 0.0967 0.022 Uiso 1 1 calc R . . C3 C 0.18441(4) 0.3767(3) 0.02215(8) 0.0165(3) Uani 1 1 d . . . H3 H 0.1854 0.2404 -0.0279 0.020 Uiso 1 1 calc R . . C4 C 0.15460(4) 0.2661(3) 0.08435(7) 0.0153(3) Uani 1 1 d . . . H4 H 0.1565 0.0542 0.0867 0.018 Uiso 1 1 calc R . . C5 C 0.10702(4) 0.3506(3) 0.05502(8) 0.0174(3) Uani 1 1 d . . . H5 H 0.1046 0.5608 0.0619 0.021 Uiso 1 1 calc R . . C6 C 0.07686(4) 0.2067(3) 0.10916(9) 0.0216(3) Uani 1 1 d . . . H6A H 0.0472 0.2776 0.0866 0.026 Uiso 1 1 calc R . . H6B H 0.0768 0.0005 0.0964 0.026 Uiso 1 1 calc R . . C7 C 0.08680(4) 0.2453(3) 0.21050(9) 0.0240(3) Uani 1 1 d . . . H7A H 0.0634 0.1573 0.2361 0.029 Uiso 1 1 calc R . . H7B H 0.0871 0.4509 0.2243 0.029 Uiso 1 1 calc R . . C8 C 0.13002(4) 0.1158(3) 0.25616(8) 0.0233(3) Uani 1 1 d . . . H8A H 0.1288 0.0725 0.3194 0.028 Uiso 1 1 calc R . . H8B H 0.1344 -0.0655 0.2261 0.028 Uiso 1 1 calc R . . C9 C 0.16799(4) 0.3077(3) 0.25380(8) 0.0182(3) Uani 1 1 d . . . C10 C 0.09129(4) 0.2749(3) -0.04501(8) 0.0211(3) Uani 1 1 d . . . H10A H 0.1113 0.3589 -0.0806 0.025 Uiso 1 1 calc R . . H10B H 0.0921 0.0661 -0.0521 0.025 Uiso 1 1 calc R . . C11 C 0.04632(5) 0.3792(3) -0.08135(9) 0.0268(3) Uani 1 1 d . . . H11 H 0.0397 0.5684 -0.0669 0.032 Uiso 1 1 calc R . . C12 C 0.01534(5) 0.2329(3) -0.13119(9) 0.0296(3) Uani 1 1 d . . . H12A H 0.0204 0.0428 -0.1473 0.036 Uiso 1 1 calc R . . H12B H -0.0122 0.3170 -0.1511 0.036 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 0.0254(5) 0.0196(5) 0.0137(4) 0.0023(3) 0.0060(4) 0.0030(4) O2 0.0254(5) 0.0339(6) 0.0136(4) -0.0021(4) 0.0044(4) -0.0033(4) N1 0.0168(5) 0.0188(5) 0.0132(5) -0.0012(4) 0.0032(4) -0.0016(4) C1 0.0158(6) 0.0198(6) 0.0160(6) 0.0010(5) 0.0029(4) -0.0016(5) C2 0.0167(6) 0.0215(6) 0.0188(6) 0.0013(5) 0.0059(5) 0.0010(5) C3 0.0186(6) 0.0172(6) 0.0145(6) -0.0009(5) 0.0055(5) 0.0019(5) C4 0.0175(6) 0.0164(6) 0.0121(6) -0.0012(4) 0.0032(5) 0.0007(5) C5 0.0164(6) 0.0197(6) 0.0161(6) -0.0021(5) 0.0031(5) 0.0008(5) C6 0.0175(6) 0.0261(7) 0.0222(7) -0.0043(5) 0.0062(5) -0.0021(5) C7 0.0207(7) 0.0317(7) 0.0222(7) -0.0037(5) 0.0106(5) -0.0049(5) C8 0.0274(7) 0.0270(7) 0.0167(6) 0.0016(5) 0.0076(5) -0.0051(6) C9 0.0205(6) 0.0197(6) 0.0150(6) 0.0000(5) 0.0051(5) 0.0022(5) C10 0.0195(6) 0.0261(7) 0.0172(6) -0.0026(5) 0.0021(5) -0.0009(5) C11 0.0262(7) 0.0270(7) 0.0254(7) 0.0002(5) 0.0005(5) 0.0033(6) C12 0.0234(7) 0.0370(8) 0.0265(7) -0.0008(6) -0.0003(6) 0.0027(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 1.4289(15) . ? O1 H1O 0.873(18) . ? O2 C9 1.2426(16) . ? N1 C9 1.3403(16) . ? N1 C1 1.4742(16) . ? N1 C4 1.4941(15) . ? C1 C2 1.5207(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.5198(17) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5459(16) . ? C3 H3 1.0000 . ? C4 C5 1.5346(17) . ? C4 H4 1.0000 . ? C5 C6 1.5305(17) . ? C5 C10 1.5463(16) . ? C5 H5 1.0000 . ? C6 C7 1.5211(18) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.533(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5071(18) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C10 C11 1.5031(18) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.311(2) . ? C11 H11 0.9500 . ? C12 H12A 0.9500 . ? C12 H12B 0.9500 . ? 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 O1 H1O 105.4(11) . . ? C9 N1 C1 119.66(10) . . ? C9 N1 C4 126.65(10) . . ? C1 N1 C4 111.60(9) . . ? N1 C1 C2 102.14(9) . . ? N1 C1 H1A 111.3 . . ? C2 C1 H1A 111.3 . . ? N1 C1 H1B 111.3 . . ? C2 C1 H1B 111.3 . . ? H1A C1 H1B 109.2 . . ? C3 C2 C1 101.99(10) . . ? C3 C2 H2A 111.4 . . ? C1 C2 H2A 111.4 . . ? C3 C2 H2B 111.4 . . ? C1 C2 H2B 111.4 . . ? H2A C2 H2B 109.2 . . ? O1 C3 C2 109.40(10) . . ? O1 C3 C4 110.13(10) . . ? C2 C3 C4 103.71(9) . . ? O1 C3 H3 111.1 . . ? C2 C3 H3 111.1 . . ? C4 C3 H3 111.1 . . ? N1 C4 C5 114.54(10) . . ? N1 C4 C3 101.95(9) . . ? C5 C4 C3 114.32(10) . . ? N1 C4 H4 108.6 . . ? C5 C4 H4 108.6 . . ? C3 C4 H4 108.6 . . ? C6 C5 C4 113.85(10) . . ? C6 C5 C10 108.06(10) . . ? C4 C5 C10 109.70(10) . . ? C6 C5 H5 108.4 . . ? C4 C5 H5 108.4 . . ? C10 C5 H5 108.4 . . ? C7 C6 C5 117.49(11) . . ? C7 C6 H6A 107.9 . . ? C5 C6 H6A 107.9 . . ? C7 C6 H6B 107.9 . . ? C5 C6 H6B 107.9 . . ? H6A C6 H6B 107.2 . . ? C6 C7 C8 113.74(11) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C9 C8 C7 113.15(11) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.8 . . ? O2 C9 N1 121.10(12) . . ? O2 C9 C8 120.92(11) . . ? N1 C9 C8 117.96(11) . . ? C11 C10 C5 112.82(11) . . ? C11 C10 H10A 109.0 . . ? C5 C10 H10A 109.0 . . ? C11 C10 H10B 109.0 . . ? C5 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 125.94(14) . . ? C12 C11 H11 117.0 . . ? C10 C11 H11 117.0 . . ? C11 C12 H12A 120.0 . . ? C11 C12 H12B 120.0 . . ? H12A C12 H12B 120.0 . . ? 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 C9 N1 C1 C2 142.30(11) . . . . ? C4 N1 C1 C2 -22.32(12) . . . . ? N1 C1 C2 C3 39.29(11) . . . . ? C1 C2 C3 O1 74.93(11) . . . . ? C1 C2 C3 C4 -42.56(12) . . . . ? C9 N1 C4 C5 68.99(16) . . . . ? C1 N1 C4 C5 -127.70(11) . . . . ? C9 N1 C4 C3 -166.98(11) . . . . ? C1 N1 C4 C3 -3.68(12) . . . . ? O1 C3 C4 N1 -88.55(11) . . . . ? C2 C3 C4 N1 28.43(11) . . . . ? O1 C3 C4 C5 35.62(13) . . . . ? C2 C3 C4 C5 152.60(10) . . . . ? N1 C4 C5 C6 -70.90(13) . . . . ? C3 C4 C5 C6 171.96(10) . . . . ? N1 C4 C5 C10 167.87(10) . . . . ? C3 C4 C5 C10 50.73(14) . . . . ? C4 C5 C6 C7 56.36(15) . . . . ? C10 C5 C6 C7 178.50(11) . . . . ? C5 C6 C7 C8 -63.85(16) . . . . ? C6 C7 C8 C9 83.18(14) . . . . ? C1 N1 C9 O2 10.91(18) . . . . ? C4 N1 C9 O2 173.01(11) . . . . ? C1 N1 C9 C8 -170.40(11) . . . . ? C4 N1 C9 C8 -8.29(18) . . . . ? C7 C8 C9 O2 117.61(13) . . . . ? C7 C8 C9 N1 -61.08(15) . . . . ? C6 C5 C10 C11 61.42(15) . . . . ? C4 C5 C10 C11 -173.93(11) . . . . ? C5 C10 C11 C12 -134.55(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O2 0.873(18) 1.836(18) 2.6966(12) 168.2(16) 2_564 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.299 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.044 data_Cmpd_25a_(k83a) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H31 N O2' _chemical_formula_weight 293.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 25.633(5) _cell_length_b 8.8841(17) _cell_length_c 15.847(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.075(4) _cell_angle_gamma 90.00 _cell_volume 3449.8(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6788 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 29.66 _exptl_crystal_description 'Square plate' _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.746 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 24493 _diffrn_reflns_av_R_equivalents 0.0694 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 24.00 _reflns_number_total 5406 _reflns_number_gt 4145 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections except those that were flagged by the user for being in the beamstop. 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^)+(0.0649P)^2^+16.3569P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5406 _refine_ls_number_parameters 421 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0870 _refine_ls_wR_factor_ref 0.2372 _refine_ls_wR_factor_gt 0.2315 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.00751(12) 0.2537(3) -0.04993(19) 0.0256(7) Uani 1 1 d . . . O2 O -0.02316(13) 0.1116(4) 0.2912(2) 0.0293(8) Uani 1 1 d . . . H2O H -0.015(2) 0.137(6) 0.350(4) 0.041(15) Uiso 1 1 d . . . N1 N -0.00447(14) 0.2241(4) 0.0841(2) 0.0202(8) Uani 1 1 d . . . C1 C -0.01865(18) 0.2809(5) 0.0025(3) 0.0217(10) Uani 1 1 d . . . C2 C -0.06872(19) 0.3800(5) -0.0217(3) 0.0276(11) Uani 1 1 d . . . H2A H -0.0706 0.4348 -0.0769 0.033 Uiso 1 1 calc R . . H2B H -0.0656 0.4555 0.0255 0.033 Uiso 1 1 calc R . . C3 C -0.12175(19) 0.2892(6) -0.0346(3) 0.0346(12) Uani 1 1 d . . . H3A H -0.1495 0.3562 -0.0222 0.042 Uiso 1 1 calc R . . H3B H -0.1355 0.2587 -0.0973 0.042 Uiso 1 1 calc R . . C4 C -0.11667(19) 0.1486(5) 0.0225(3) 0.0287(11) Uani 1 1 d . . . H4A H -0.0940 0.0745 0.0025 0.034 Uiso 1 1 calc R . . H4B H -0.1535 0.1042 0.0115 0.034 Uiso 1 1 calc R . . C5 C -0.09225(17) 0.1693(5) 0.1223(3) 0.0237(10) Uani 1 1 d . . . H5 H -0.0876 0.0666 0.1493 0.028 Uiso 1 1 calc R . . C6 C -0.03532(17) 0.2448(5) 0.1491(3) 0.0200(9) Uani 1 1 d . . . H6 H -0.0381(17) 0.351(6) 0.157(3) 0.022(12) Uiso 1 1 d . . . C7 C 0.00366(18) 0.1746(5) 0.2336(3) 0.0229(10) Uani 1 1 d . . . H7 H 0.0298 0.2533 0.2659 0.028 Uiso 1 1 calc R . . C8 C 0.03450(19) 0.0575(5) 0.1977(3) 0.0238(10) Uani 1 1 d . . . H8A H 0.0693 0.0311 0.2423 0.029 Uiso 1 1 calc R . . H8B H 0.0124 -0.0350 0.1804 0.029 Uiso 1 1 calc R . . C9 C 0.04492(17) 0.1306(5) 0.1182(3) 0.0206(10) Uani 1 1 d . . . H9 H 0.0466 0.0523 0.0738 0.025 Uiso 1 1 calc R . . C10 C 0.09635(17) 0.2291(5) 0.1401(3) 0.0238(10) Uani 1 1 d . . . H10A H 0.0964 0.2871 0.0868 0.029 Uiso 1 1 calc R . . H10B H 0.0946 0.3023 0.1864 0.029 Uiso 1 1 calc R . . C11 C 0.14958(18) 0.1428(5) 0.1718(3) 0.0265(10) Uani 1 1 d . . . H11A H 0.1532 0.0760 0.1238 0.032 Uiso 1 1 calc R . . H11B H 0.1487 0.0786 0.2224 0.032 Uiso 1 1 calc R . . C12 C 0.19892(18) 0.2461(5) 0.1996(3) 0.0277(11) Uani 1 1 d . . . H12A H 0.1988 0.3118 0.1491 0.033 Uiso 1 1 calc R . . H12B H 0.1950 0.3118 0.2479 0.033 Uiso 1 1 calc R . . C13 C 0.25340(19) 0.1679(6) 0.2304(3) 0.0293(11) Uani 1 1 d . . . H13A H 0.2589 0.1085 0.1809 0.035 Uiso 1 1 calc R . . H13B H 0.2530 0.0969 0.2783 0.035 Uiso 1 1 calc R . . C14 C 0.30075(19) 0.2753(6) 0.2635(3) 0.0349(12) Uani 1 1 d . . . H14A H 0.3007 0.3473 0.2158 0.042 Uiso 1 1 calc R . . H14B H 0.2953 0.3338 0.3135 0.042 Uiso 1 1 calc R . . C15 C 0.35570(19) 0.1988(6) 0.2934(3) 0.0375(13) Uani 1 1 d . . . H15A H 0.3843 0.2745 0.3150 0.056 Uiso 1 1 calc R . . H15B H 0.3622 0.1443 0.2437 0.056 Uiso 1 1 calc R . . H15C H 0.3563 0.1277 0.3410 0.056 Uiso 1 1 calc R . . C16 C -0.13000(18) 0.2576(5) 0.1638(3) 0.0285(11) Uani 1 1 d . . . H16A H -0.1098 0.2818 0.2257 0.034 Uiso 1 1 calc R . . H16B H -0.1401 0.3538 0.1316 0.034 Uiso 1 1 calc R . . C17 C -0.1808(2) 0.1744(6) 0.1623(4) 0.0397(13) Uani 1 1 d . . . H17 H -0.172(2) 0.079(7) 0.200(4) 0.053(17) Uiso 1 1 d . . . C18 C -0.2306(3) 0.2145(8) 0.1206(6) 0.068(2) Uani 1 1 d . . . H18A H -0.2328(19) 0.324(6) 0.090(3) 0.029(13) Uiso 1 1 d . . . H18B H -0.265(3) 0.162(9) 0.120(5) 0.09(2) Uiso 1 1 d . . . O21 O 0.49014(12) 0.2521(4) 0.44514(19) 0.0269(7) Uani 1 1 d . . . O22 O 0.51716(13) 0.3912(4) 0.8146(2) 0.0293(8) Uani 1 1 d . . . H22O H 0.506(3) 0.329(9) 0.866(5) 0.09(2) Uiso 1 1 d . . . N21 N 0.50120(14) 0.2793(4) 0.5908(2) 0.0190(8) Uani 1 1 d . . . C21 C 0.51659(18) 0.2280(5) 0.5234(3) 0.0222(10) Uani 1 1 d . . . C22 C 0.56863(18) 0.1336(5) 0.5464(3) 0.0250(10) Uani 1 1 d . . . H22A H 0.5712 0.0798 0.4930 0.030 Uiso 1 1 calc R . . H22B H 0.5672 0.0575 0.5913 0.030 Uiso 1 1 calc R . . C23 C 0.61993(19) 0.2343(6) 0.5827(3) 0.0312(11) Uani 1 1 d . . . H23A H 0.6497 0.1717 0.6203 0.037 Uiso 1 1 calc R . . H23B H 0.6319 0.2705 0.5323 0.037 Uiso 1 1 calc R . . C24 C 0.61163(19) 0.3695(5) 0.6360(3) 0.0284(11) Uani 1 1 d . . . H24A H 0.5874 0.4413 0.5948 0.034 Uiso 1 1 calc R . . H24B H 0.6474 0.4197 0.6602 0.034 Uiso 1 1 calc R . . C25 C 0.58766(18) 0.3410(5) 0.7124(3) 0.0231(10) Uani 1 1 d . . . H25 H 0.5816 0.4416 0.7363 0.028 Uiso 1 1 calc R . . C26 C 0.53201(18) 0.2596(5) 0.6847(3) 0.0192(9) Uani 1 1 d . . . H26 H 0.5414(18) 0.161(6) 0.701(3) 0.025(12) Uiso 1 1 d . . . C27 C 0.49153(18) 0.3250(5) 0.7317(3) 0.0234(10) Uani 1 1 d . . . H27 H 0.4665 0.2432 0.7394 0.028 Uiso 1 1 calc R . . C28 C 0.45907(18) 0.4398(5) 0.6660(3) 0.0236(10) Uani 1 1 d . . . H28A H 0.4239 0.4626 0.6773 0.028 Uiso 1 1 calc R . . H28B H 0.4799 0.5345 0.6691 0.028 Uiso 1 1 calc R . . C29 C 0.44976(18) 0.3645(5) 0.5769(3) 0.0219(10) Uani 1 1 d . . . H29 H 0.4464 0.4422 0.5300 0.026 Uiso 1 1 calc R . . C30 C 0.40079(17) 0.2576(5) 0.5508(3) 0.0231(10) Uani 1 1 d . . . H30A H 0.4035 0.1953 0.5005 0.028 Uiso 1 1 calc R . . H30B H 0.4029 0.1890 0.6009 0.028 Uiso 1 1 calc R . . C31 C 0.34516(18) 0.3353(5) 0.5251(3) 0.0250(10) Uani 1 1 d . . . H31A H 0.3423 0.3994 0.5747 0.030 Uiso 1 1 calc R . . H31B H 0.3421 0.4013 0.4736 0.030 Uiso 1 1 calc R . . C32 C 0.29864(17) 0.2236(5) 0.5026(3) 0.0246(10) Uani 1 1 d . . . H32A H 0.3012 0.1615 0.5556 0.030 Uiso 1 1 calc R . . H32B H 0.3035 0.1554 0.4561 0.030 Uiso 1 1 calc R . . C33 C 0.24167(18) 0.2901(5) 0.4711(3) 0.0269(11) Uani 1 1 d . . . H33A H 0.2390 0.3548 0.4192 0.032 Uiso 1 1 calc R . . H33B H 0.2357 0.3546 0.5184 0.032 Uiso 1 1 calc R . . C34 C 0.19680(18) 0.1711(6) 0.4462(3) 0.0302(11) Uani 1 1 d . . . H34A H 0.2029 0.1070 0.3989 0.036 Uiso 1 1 calc R . . H34B H 0.1998 0.1060 0.4982 0.036 Uiso 1 1 calc R . . C35 C 0.13998(19) 0.2340(6) 0.4154(3) 0.0330(12) Uani 1 1 d . . . H35A H 0.1136 0.1512 0.4012 0.050 Uiso 1 1 calc R . . H35B H 0.1361 0.2958 0.3626 0.050 Uiso 1 1 calc R . . H35C H 0.1332 0.2962 0.4622 0.050 Uiso 1 1 calc R . . C36 C 0.62658(18) 0.2523(5) 0.7892(3) 0.0267(10) Uani 1 1 d . . . H36A H 0.6066 0.2229 0.8314 0.032 Uiso 1 1 calc R . . H36B H 0.6381 0.1590 0.7655 0.032 Uiso 1 1 calc R . . C37 C 0.6760(2) 0.3394(6) 0.8371(4) 0.0409(14) Uani 1 1 d . . . H37 H 0.671(2) 0.429(7) 0.874(4) 0.056(18) Uiso 1 1 d . . . C38 C 0.7263(3) 0.3045(10) 0.8430(6) 0.074(3) Uani 1 1 d . . . H38A H 0.762(3) 0.379(10) 0.879(5) 0.11(3) Uiso 1 1 d . . . H38B H 0.733(4) 0.218(11) 0.830(6) 0.11(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0303(17) 0.0235(17) 0.0243(17) -0.0001(14) 0.0101(14) 0.0018(14) O2 0.041(2) 0.0298(19) 0.0206(18) 0.0004(15) 0.0148(15) -0.0053(15) N1 0.0180(18) 0.0170(19) 0.026(2) -0.0022(16) 0.0065(15) 0.0014(15) C1 0.026(2) 0.018(2) 0.019(2) -0.0043(18) 0.0039(19) -0.0054(19) C2 0.035(3) 0.027(3) 0.021(2) 0.004(2) 0.008(2) 0.009(2) C3 0.025(3) 0.046(3) 0.029(3) 0.002(2) 0.002(2) 0.004(2) C4 0.027(2) 0.030(3) 0.030(3) -0.009(2) 0.009(2) -0.003(2) C5 0.025(2) 0.019(2) 0.028(2) -0.0023(19) 0.0095(19) -0.0017(19) C6 0.024(2) 0.012(2) 0.025(2) -0.0016(18) 0.0089(18) -0.0013(18) C7 0.031(2) 0.017(2) 0.022(2) 0.0000(18) 0.0102(19) -0.0024(19) C8 0.030(3) 0.018(2) 0.023(2) 0.0001(19) 0.0071(19) 0.0013(19) C9 0.025(2) 0.016(2) 0.021(2) 0.0002(18) 0.0066(18) 0.0067(18) C10 0.024(2) 0.013(2) 0.033(3) 0.0037(19) 0.0069(19) 0.0018(19) C11 0.028(3) 0.022(2) 0.029(3) 0.001(2) 0.007(2) 0.001(2) C12 0.029(3) 0.024(3) 0.030(3) -0.001(2) 0.008(2) -0.002(2) C13 0.031(3) 0.032(3) 0.025(2) -0.002(2) 0.009(2) -0.002(2) C14 0.033(3) 0.041(3) 0.031(3) -0.001(2) 0.010(2) -0.004(2) C15 0.028(3) 0.049(3) 0.035(3) -0.014(3) 0.008(2) 0.000(2) C16 0.028(3) 0.022(2) 0.037(3) -0.004(2) 0.012(2) -0.001(2) C17 0.036(3) 0.031(3) 0.058(4) -0.010(3) 0.023(3) -0.002(2) C18 0.037(4) 0.045(4) 0.128(7) -0.025(4) 0.033(4) -0.006(3) O21 0.0306(17) 0.0274(18) 0.0203(17) -0.0011(14) 0.0038(14) 0.0030(14) O22 0.040(2) 0.0278(18) 0.0187(16) -0.0013(14) 0.0073(14) -0.0029(15) N21 0.0242(19) 0.0166(18) 0.0144(18) 0.0001(15) 0.0027(15) -0.0012(15) C21 0.027(2) 0.018(2) 0.021(2) -0.0020(19) 0.0054(19) -0.0036(19) C22 0.028(2) 0.023(2) 0.025(2) -0.002(2) 0.0089(19) 0.004(2) C23 0.027(3) 0.035(3) 0.032(3) -0.002(2) 0.009(2) -0.003(2) C24 0.026(2) 0.028(3) 0.028(3) 0.006(2) 0.003(2) -0.002(2) C25 0.029(2) 0.015(2) 0.022(2) 0.0009(18) 0.0036(19) -0.0013(19) C26 0.025(2) 0.013(2) 0.019(2) 0.0002(18) 0.0063(18) -0.0030(19) C27 0.026(2) 0.022(2) 0.020(2) -0.0001(19) 0.0038(19) 0.0014(19) C28 0.029(2) 0.020(2) 0.023(2) -0.0003(19) 0.0092(19) 0.001(2) C29 0.031(2) 0.017(2) 0.018(2) 0.0029(18) 0.0068(18) 0.0021(19) C30 0.028(2) 0.018(2) 0.022(2) -0.0005(19) 0.0051(19) -0.0002(19) C31 0.029(3) 0.021(2) 0.024(2) 0.0035(19) 0.0065(19) 0.003(2) C32 0.027(2) 0.020(2) 0.026(2) 0.0055(19) 0.0065(19) 0.0017(19) C33 0.029(3) 0.029(3) 0.023(2) 0.004(2) 0.0075(19) 0.001(2) C34 0.027(3) 0.036(3) 0.028(3) 0.004(2) 0.009(2) -0.003(2) C35 0.029(3) 0.038(3) 0.034(3) -0.005(2) 0.011(2) -0.003(2) C36 0.029(3) 0.018(2) 0.029(3) 0.003(2) 0.001(2) -0.003(2) C37 0.044(3) 0.032(3) 0.036(3) 0.006(2) -0.004(2) -0.006(3) C38 0.036(4) 0.055(5) 0.107(6) 0.021(5) -0.019(4) -0.013(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.236(5) . ? O2 C7 1.410(5) . ? O2 H2O 0.92(6) . ? N1 C1 1.335(6) . ? N1 C9 1.477(5) . ? N1 C6 1.482(5) . ? C1 C2 1.510(6) . ? C2 C3 1.542(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.525(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.531(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C16 1.535(6) . ? C5 C6 1.548(6) . ? C5 H5 1.0000 . ? C6 C7 1.548(6) . ? C6 H6 0.95(5) . ? C7 C8 1.515(6) . ? C7 H7 1.0000 . ? C8 C9 1.509(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.535(6) . ? C9 H9 1.0000 . ? C10 C11 1.516(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.520(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.507(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.512(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.510(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.491(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.303(9) . ? C17 H17 1.02(6) . ? C18 H18A 1.08(5) . ? C18 H18B 0.99(7) . ? O21 C21 1.244(5) . ? O22 C27 1.413(5) . ? O22 H22O 1.09(8) . ? N21 C21 1.324(6) . ? N21 C26 1.476(5) . ? N21 C29 1.479(6) . ? C21 C22 1.527(6) . ? C22 C23 1.554(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.519(7) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.532(6) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C36 1.544(6) . ? C25 C26 1.544(6) . ? C25 H25 1.0000 . ? C26 C27 1.557(6) . ? C26 H26 0.92(5) . ? C27 C28 1.520(6) . ? C27 H27 1.0000 . ? C28 C29 1.516(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.530(6) . ? C29 H29 1.0000 . ? C30 C31 1.528(6) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.511(6) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.517(6) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.526(6) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.502(6) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 C37 1.489(7) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.302(10) . ? C37 H37 1.02(6) . ? C38 H38A 1.13(8) . ? C38 H38B 0.83(9) . ? 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 C7 O2 H2O 123(3) . . ? C1 N1 C9 121.8(4) . . ? C1 N1 C6 125.2(4) . . ? C9 N1 C6 113.0(3) . . ? O1 C1 N1 122.0(4) . . ? O1 C1 C2 122.1(4) . . ? N1 C1 C2 115.8(4) . . ? C1 C2 C3 112.3(4) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 115.6(4) . . ? C4 C3 H3A 108.4 . . ? C2 C3 H3A 108.4 . . ? C4 C3 H3B 108.4 . . ? C2 C3 H3B 108.4 . . ? H3A C3 H3B 107.5 . . ? C3 C4 C5 116.9(4) . . ? C3 C4 H4A 108.1 . . ? C5 C4 H4A 108.1 . . ? C3 C4 H4B 108.1 . . ? C5 C4 H4B 108.1 . . ? H4A C4 H4B 107.3 . . ? C4 C5 C16 112.7(4) . . ? C4 C5 C6 113.7(4) . . ? C16 C5 C6 108.9(4) . . ? C4 C5 H5 107.1 . . ? C16 C5 H5 107.1 . . ? C6 C5 H5 107.1 . . ? N1 C6 C7 102.2(3) . . ? N1 C6 C5 114.1(3) . . ? C7 C6 C5 112.3(4) . . ? N1 C6 H6 107(3) . . ? C7 C6 H6 110(3) . . ? C5 C6 H6 111(3) . . ? O2 C7 C8 112.2(4) . . ? O2 C7 C6 114.0(4) . . ? C8 C7 C6 103.1(3) . . ? O2 C7 H7 109.1 . . ? C8 C7 H7 109.1 . . ? C6 C7 H7 109.1 . . ? C9 C8 C7 104.9(4) . . ? C9 C8 H8A 110.8 . . ? C7 C8 H8A 110.8 . . ? C9 C8 H8B 110.8 . . ? C7 C8 H8B 110.8 . . ? H8A C8 H8B 108.8 . . ? N1 C9 C8 101.8(3) . . ? N1 C9 C10 110.4(3) . . ? C8 C9 C10 114.0(4) . . ? N1 C9 H9 110.1 . . ? C8 C9 H9 110.1 . . ? C10 C9 H9 110.1 . . ? C11 C10 C9 114.6(4) . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 112.5(4) . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 115.4(4) . . ? C13 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? C13 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C12 C13 C14 113.2(4) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C13 113.8(4) . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? 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 . . ? C17 C16 C5 113.4(4) . . ? C17 C16 H16A 108.9 . . ? C5 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C5 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C16 126.4(6) . . ? C18 C17 H17 123(3) . . ? C16 C17 H17 110(3) . . ? C17 C18 H18A 113(3) . . ? C17 C18 H18B 127(4) . . ? H18A C18 H18B 120(5) . . ? C27 O22 H22O 109(4) . . ? C21 N21 C26 125.1(4) . . ? C21 N21 C29 121.3(3) . . ? C26 N21 C29 113.6(3) . . ? O21 C21 N21 122.7(4) . . ? O21 C21 C22 121.0(4) . . ? N21 C21 C22 116.3(4) . . ? C21 C22 C23 110.9(4) . . ? C21 C22 H22A 109.5 . . ? C23 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 108.0 . . ? C24 C23 C22 114.8(4) . . ? C24 C23 H23A 108.6 . . ? C22 C23 H23A 108.6 . . ? C24 C23 H23B 108.6 . . ? C22 C23 H23B 108.6 . . ? H23A C23 H23B 107.5 . . ? C23 C24 C25 117.6(4) . . ? C23 C24 H24A 107.9 . . ? C25 C24 H24A 107.9 . . ? C23 C24 H24B 107.9 . . ? C25 C24 H24B 107.9 . . ? H24A C24 H24B 107.2 . . ? C24 C25 C36 113.0(4) . . ? C24 C25 C26 113.8(4) . . ? C36 C25 C26 108.3(4) . . ? C24 C25 H25 107.1 . . ? C36 C25 H25 107.1 . . ? C26 C25 H25 107.1 . . ? N21 C26 C25 114.0(3) . . ? N21 C26 C27 101.7(3) . . ? C25 C26 C27 112.3(4) . . ? N21 C26 H26 115(3) . . ? C25 C26 H26 103(3) . . ? C27 C26 H26 112(3) . . ? O22 C27 C28 111.7(4) . . ? O22 C27 C26 114.0(3) . . ? C28 C27 C26 103.3(3) . . ? O22 C27 H27 109.2 . . ? C28 C27 H27 109.2 . . ? C26 C27 H27 109.2 . . ? C29 C28 C27 104.3(4) . . ? C29 C28 H28A 110.9 . . ? C27 C28 H28A 110.9 . . ? C29 C28 H28B 110.9 . . ? C27 C28 H28B 110.9 . . ? H28A C28 H28B 108.9 . . ? N21 C29 C28 101.4(3) . . ? N21 C29 C30 110.3(3) . . ? C28 C29 C30 114.7(4) . . ? N21 C29 H29 110.0 . . ? C28 C29 H29 110.0 . . ? C30 C29 H29 110.0 . . ? C31 C30 C29 114.8(4) . . ? C31 C30 H30A 108.6 . . ? C29 C30 H30A 108.6 . . ? C31 C30 H30B 108.6 . . ? C29 C30 H30B 108.6 . . ? H30A C30 H30B 107.5 . . ? C32 C31 C30 112.1(4) . . ? C32 C31 H31A 109.2 . . ? C30 C31 H31A 109.2 . . ? C32 C31 H31B 109.2 . . ? C30 C31 H31B 109.2 . . ? H31A C31 H31B 107.9 . . ? C31 C32 C33 116.0(4) . . ? C31 C32 H32A 108.3 . . ? C33 C32 H32A 108.3 . . ? C31 C32 H32B 108.3 . . ? C33 C32 H32B 108.3 . . ? H32A C32 H32B 107.4 . . ? C32 C33 C34 113.3(4) . . ? C32 C33 H33A 108.9 . . ? C34 C33 H33A 108.9 . . ? C32 C33 H33B 108.9 . . ? C34 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? C35 C34 C33 114.3(4) . . ? C35 C34 H34A 108.7 . . ? C33 C34 H34A 108.7 . . ? C35 C34 H34B 108.7 . . ? C33 C34 H34B 108.7 . . ? H34A C34 H34B 107.6 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C37 C36 C25 113.2(4) . . ? C37 C36 H36A 108.9 . . ? C25 C36 H36A 108.9 . . ? C37 C36 H36B 108.9 . . ? C25 C36 H36B 108.9 . . ? H36A C36 H36B 107.8 . . ? C38 C37 C36 126.1(6) . . ? C38 C37 H37 116(3) . . ? C36 C37 H37 118(3) . . ? C37 C38 H38A 122(4) . . ? C37 C38 H38B 119(7) . . ? H38A C38 H38B 118(7) . . ? 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 C9 N1 C1 O1 2.9(6) . . . . ? C6 N1 C1 O1 -176.6(4) . . . . ? C9 N1 C1 C2 -177.3(4) . . . . ? C6 N1 C1 C2 3.2(6) . . . . ? O1 C1 C2 C3 107.7(5) . . . . ? N1 C1 C2 C3 -72.1(5) . . . . ? C1 C2 C3 C4 31.8(6) . . . . ? C2 C3 C4 C5 54.1(6) . . . . ? C3 C4 C5 C16 69.1(5) . . . . ? C3 C4 C5 C6 -55.3(5) . . . . ? C1 N1 C6 C7 -172.6(4) . . . . ? C9 N1 C6 C7 8.0(4) . . . . ? C1 N1 C6 C5 66.0(5) . . . . ? C9 N1 C6 C5 -113.5(4) . . . . ? C4 C5 C6 N1 -25.2(5) . . . . ? C16 C5 C6 N1 -151.7(4) . . . . ? C4 C5 C6 C7 -140.9(4) . . . . ? C16 C5 C6 C7 92.6(4) . . . . ? N1 C6 C7 O2 -150.3(4) . . . . ? C5 C6 C7 O2 -27.6(5) . . . . ? N1 C6 C7 C8 -28.4(4) . . . . ? C5 C6 C7 C8 94.3(4) . . . . ? O2 C7 C8 C9 162.6(4) . . . . ? C6 C7 C8 C9 39.5(4) . . . . ? C1 N1 C9 C8 -163.7(4) . . . . ? C6 N1 C9 C8 15.8(4) . . . . ? C1 N1 C9 C10 74.8(5) . . . . ? C6 N1 C9 C10 -105.7(4) . . . . ? C7 C8 C9 N1 -33.7(4) . . . . ? C7 C8 C9 C10 85.2(4) . . . . ? N1 C9 C10 C11 -177.3(4) . . . . ? C8 C9 C10 C11 68.8(5) . . . . ? C9 C10 C11 C12 -175.3(4) . . . . ? C10 C11 C12 C13 -179.0(4) . . . . ? C11 C12 C13 C14 -175.8(4) . . . . ? C12 C13 C14 C15 -179.2(4) . . . . ? C4 C5 C16 C17 67.8(5) . . . . ? C6 C5 C16 C17 -165.1(4) . . . . ? C5 C16 C17 C18 -116.8(7) . . . . ? C26 N21 C21 O21 -177.4(4) . . . . ? C29 N21 C21 O21 2.4(6) . . . . ? C26 N21 C21 C22 3.8(6) . . . . ? C29 N21 C21 C22 -176.3(4) . . . . ? O21 C21 C22 C23 107.4(5) . . . . ? N21 C21 C22 C23 -73.7(5) . . . . ? C21 C22 C23 C24 33.5(5) . . . . ? C22 C23 C24 C25 52.6(6) . . . . ? C23 C24 C25 C36 67.6(5) . . . . ? C23 C24 C25 C26 -56.5(5) . . . . ? C21 N21 C26 C25 65.3(5) . . . . ? C29 N21 C26 C25 -114.6(4) . . . . ? C21 N21 C26 C27 -173.6(4) . . . . ? C29 N21 C26 C27 6.5(4) . . . . ? C24 C25 C26 N21 -24.3(5) . . . . ? C36 C25 C26 N21 -150.9(4) . . . . ? C24 C25 C26 C27 -139.4(4) . . . . ? C36 C25 C26 C27 94.0(4) . . . . ? N21 C26 C27 O22 -149.4(4) . . . . ? C25 C26 C27 O22 -27.1(5) . . . . ? N21 C26 C27 C28 -28.0(4) . . . . ? C25 C26 C27 C28 94.3(4) . . . . ? O22 C27 C28 C29 163.0(4) . . . . ? C26 C27 C28 C29 40.0(4) . . . . ? C21 N21 C29 C28 -162.3(4) . . . . ? C26 N21 C29 C28 17.6(4) . . . . ? C21 N21 C29 C30 75.8(5) . . . . ? C26 N21 C29 C30 -104.3(4) . . . . ? C27 C28 C29 N21 -35.0(4) . . . . ? C27 C28 C29 C30 83.9(4) . . . . ? N21 C29 C30 C31 -173.7(3) . . . . ? C28 C29 C30 C31 72.6(5) . . . . ? C29 C30 C31 C32 -178.4(4) . . . . ? C30 C31 C32 C33 -176.6(4) . . . . ? C31 C32 C33 C34 177.8(4) . . . . ? C32 C33 C34 C35 179.7(4) . . . . ? C24 C25 C36 C37 68.1(5) . . . . ? C26 C25 C36 C37 -164.8(4) . . . . ? C25 C36 C37 C38 -117.5(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O1 0.92(6) 1.80(6) 2.689(4) 160(5) 4_566 O22 H22O O21 1.09(8) 1.60(8) 2.687(4) 176(7) 4_566 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.389 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.071 data_Cmpd_26a_(k16g) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H23 N O2' _chemical_formula_weight 237.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.5311(5) _cell_length_b 15.1592(9) _cell_length_c 18.9260(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2734.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9721 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 30.34 _exptl_crystal_description 'Rectangular parallelepiped' _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 30778 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 30.49 _reflns_number_total 4159 _reflns_number_gt 3666 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0781P)^2^+0.2044P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4159 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 0.27030(8) 0.42293(4) 0.38528(4) 0.02163(18) Uani 1 1 d . . . O2 O 0.22764(8) 0.09376(5) 0.42553(4) 0.01806(17) Uani 1 1 d . . . H2O H 0.2272(16) 0.0394(11) 0.4090(8) 0.035(4) Uiso 1 1 d . . . N N 0.31196(8) 0.28231(5) 0.41696(4) 0.01394(17) Uani 1 1 d . . . C1 C 0.31924(10) 0.36970(6) 0.42889(5) 0.01548(19) Uani 1 1 d . . . C2 C 0.38591(10) 0.40146(6) 0.49645(5) 0.0180(2) Uani 1 1 d . . . H2A H 0.4858(15) 0.3844(9) 0.4969(7) 0.023(3) Uiso 1 1 d . . . H2B H 0.3798(14) 0.4658(9) 0.4944(6) 0.024(3) Uiso 1 1 d . . . C3 C 0.31574(11) 0.36664(7) 0.56355(5) 0.0196(2) Uani 1 1 d . . . H3A H 0.3398(16) 0.4063(9) 0.6024(8) 0.034(4) Uiso 1 1 d . . . H3B H 0.2118(14) 0.3684(9) 0.5580(8) 0.025(3) Uiso 1 1 d . . . C4 C 0.36432(11) 0.27462(7) 0.58458(5) 0.0187(2) Uani 1 1 d . . . H4A H 0.4678(14) 0.2743(9) 0.5897(7) 0.024(3) Uiso 1 1 d . . . H4B H 0.3272(14) 0.2586(9) 0.6333(8) 0.027(3) Uiso 1 1 d . . . C5 C 0.32524(10) 0.19894(6) 0.53481(5) 0.01437(18) Uani 1 1 d . . . H5 H 0.2218(13) 0.1933(8) 0.5331(7) 0.017(3) Uiso 1 1 d . . . C6 C 0.38110(9) 0.21160(6) 0.45943(5) 0.01299(18) Uani 1 1 d . . . H6 H 0.4814(13) 0.2245(8) 0.4629(7) 0.018(3) Uiso 1 1 d . . . C7 C 0.36134(10) 0.13072(6) 0.41103(5) 0.01417(18) Uani 1 1 d . . . H7 H 0.4379(13) 0.0880(8) 0.4196(6) 0.016(3) Uiso 1 1 d . . . C8 C 0.36571(10) 0.16973(6) 0.33591(5) 0.01525(19) Uani 1 1 d . . . C9 C 0.27153(10) 0.25034(6) 0.34610(5) 0.01511(19) Uani 1 1 d . . . H9A H 0.1701(13) 0.2348(9) 0.3449(7) 0.019(3) Uiso 1 1 d . . . H9B H 0.2865(14) 0.2977(9) 0.3117(8) 0.022(3) Uiso 1 1 d . . . C10 C 0.38548(12) 0.11239(6) 0.56577(5) 0.0191(2) Uani 1 1 d . . . H10A H 0.4873(16) 0.1163(9) 0.5676(8) 0.031(4) Uiso 1 1 d . . . H10B H 0.3619(14) 0.0633(9) 0.5342(8) 0.026(3) Uiso 1 1 d . . . C11 C 0.33146(13) 0.09140(7) 0.63839(6) 0.0249(2) Uani 1 1 d . . . H11 H 0.2336(15) 0.0837(9) 0.6421(8) 0.027(4) Uiso 1 1 d . . . C12 C 0.41143(17) 0.08286(8) 0.69537(6) 0.0331(3) Uani 1 1 d . . . H12A H 0.3711(16) 0.0678(10) 0.7428(10) 0.044(4) Uiso 1 1 d . . . H12B H 0.516(2) 0.0909(11) 0.6905(11) 0.054(5) Uiso 1 1 d . . . C13 C 0.51477(11) 0.19862(8) 0.31678(6) 0.0242(2) Uani 1 1 d . . . H13A H 0.5177(17) 0.2233(11) 0.2670(9) 0.042(4) Uiso 1 1 d . . . H13B H 0.5529(15) 0.2456(9) 0.3495(8) 0.031(4) Uiso 1 1 d . . . H13C H 0.5790(15) 0.1478(10) 0.3191(7) 0.032(4) Uiso 1 1 d . . . C14 C 0.31059(12) 0.10604(7) 0.28020(5) 0.0218(2) Uani 1 1 d . . . H14A H 0.2113(16) 0.0869(9) 0.2892(8) 0.027(4) Uiso 1 1 d . . . H14B H 0.3124(15) 0.1321(11) 0.2343(8) 0.036(4) Uiso 1 1 d . . . H14C H 0.3687(16) 0.0529(11) 0.2770(8) 0.040(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0304(4) 0.0116(3) 0.0229(4) 0.0015(3) -0.0036(3) 0.0030(3) O2 0.0215(4) 0.0114(3) 0.0213(4) -0.0015(2) 0.0019(3) -0.0047(3) N 0.0158(4) 0.0096(4) 0.0165(4) 0.0006(3) -0.0014(3) 0.0003(3) C1 0.0154(4) 0.0106(4) 0.0204(4) 0.0000(3) 0.0018(3) -0.0007(3) C2 0.0188(5) 0.0117(4) 0.0234(5) -0.0011(3) -0.0035(3) -0.0025(3) C3 0.0261(5) 0.0132(4) 0.0193(5) -0.0030(3) -0.0016(4) 0.0011(4) C4 0.0243(5) 0.0140(4) 0.0179(4) -0.0013(3) -0.0030(4) 0.0005(4) C5 0.0164(4) 0.0115(4) 0.0152(4) 0.0001(3) -0.0007(3) 0.0009(3) C6 0.0128(4) 0.0100(4) 0.0162(4) 0.0008(3) -0.0008(3) 0.0012(3) C7 0.0158(4) 0.0102(4) 0.0165(4) 0.0000(3) 0.0002(3) 0.0016(3) C8 0.0174(4) 0.0128(4) 0.0155(4) 0.0003(3) 0.0009(3) 0.0030(3) C9 0.0178(4) 0.0120(4) 0.0156(4) -0.0001(3) -0.0013(3) 0.0020(3) C10 0.0261(5) 0.0139(4) 0.0174(4) 0.0018(3) 0.0003(4) 0.0035(4) C11 0.0358(6) 0.0159(5) 0.0229(5) 0.0041(4) 0.0061(4) 0.0021(4) C12 0.0590(9) 0.0197(5) 0.0207(5) 0.0039(4) 0.0012(5) 0.0066(5) C13 0.0188(5) 0.0315(6) 0.0222(5) 0.0033(4) 0.0054(4) 0.0026(4) C14 0.0319(6) 0.0166(5) 0.0168(5) -0.0022(4) -0.0037(4) 0.0063(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2449(12) . ? O2 C7 1.4188(12) . ? O2 H2O 0.882(16) . ? N C1 1.3457(12) . ? N C9 1.4771(12) . ? N C6 1.4931(11) . ? C1 C2 1.5067(13) . ? C2 C3 1.5292(14) . ? C2 H2A 0.986(14) . ? C2 H2B 0.977(14) . ? C3 C4 1.5227(14) . ? C3 H3A 0.977(15) . ? C3 H3B 0.996(14) . ? C4 C5 1.5304(13) . ? C4 H4A 0.991(13) . ? C4 H4B 1.018(15) . ? C5 C6 1.5347(13) . ? C5 C10 1.5474(13) . ? C5 H5 0.990(13) . ? C6 C7 1.5421(12) . ? C6 H6 0.978(13) . ? C7 C8 1.5405(13) . ? C7 H7 0.989(12) . ? C8 C14 1.5231(14) . ? C8 C9 1.5284(13) . ? C8 C13 1.5301(14) . ? C9 H9A 0.995(12) . ? C9 H9B 0.980(14) . ? C10 C11 1.5018(14) . ? C10 H10A 0.973(15) . ? C10 H10B 0.981(14) . ? C11 C12 1.3269(18) . ? C11 H11 0.943(14) . ? C12 H12A 1.003(17) . ? C12 H12B 1.013(19) . ? C13 H13A 1.013(17) . ? C13 H13B 1.011(15) . ? C13 H13C 0.984(15) . ? C14 H14A 1.005(15) . ? C14 H14B 0.955(16) . ? C14 H14C 0.979(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O2 H2O 107.7(10) . . ? C1 N C9 119.27(8) . . ? C1 N C6 126.41(8) . . ? C9 N C6 111.62(7) . . ? O1 C1 N 120.49(9) . . ? O1 C1 C2 120.90(9) . . ? N C1 C2 118.60(8) . . ? C1 C2 C3 114.20(8) . . ? C1 C2 H2A 109.3(8) . . ? C3 C2 H2A 108.9(8) . . ? C1 C2 H2B 105.1(7) . . ? C3 C2 H2B 110.6(7) . . ? H2A C2 H2B 108.6(11) . . ? C4 C3 C2 113.60(9) . . ? C4 C3 H3A 107.2(8) . . ? C2 C3 H3A 108.0(9) . . ? C4 C3 H3B 110.7(8) . . ? C2 C3 H3B 109.8(8) . . ? H3A C3 H3B 107.2(12) . . ? C3 C4 C5 116.86(8) . . ? C3 C4 H4A 109.4(8) . . ? C5 C4 H4A 107.4(8) . . ? C3 C4 H4B 110.4(8) . . ? C5 C4 H4B 107.2(8) . . ? H4A C4 H4B 104.8(11) . . ? C4 C5 C6 113.20(8) . . ? C4 C5 C10 108.19(8) . . ? C6 C5 C10 109.23(7) . . ? C4 C5 H5 109.1(7) . . ? C6 C5 H5 109.0(7) . . ? C10 C5 H5 108.0(7) . . ? N C6 C5 115.92(7) . . ? N C6 C7 101.37(7) . . ? C5 C6 C7 114.23(7) . . ? N C6 H6 108.9(7) . . ? C5 C6 H6 107.5(7) . . ? C7 C6 H6 108.5(7) . . ? O2 C7 C8 110.75(8) . . ? O2 C7 C6 107.98(7) . . ? C8 C7 C6 103.87(7) . . ? O2 C7 H7 111.9(7) . . ? C8 C7 H7 112.5(7) . . ? C6 C7 H7 109.4(7) . . ? C14 C8 C9 113.06(8) . . ? C14 C8 C13 109.75(8) . . ? C9 C8 C13 110.27(8) . . ? C14 C8 C7 112.72(8) . . ? C9 C8 C7 100.05(7) . . ? C13 C8 C7 110.69(8) . . ? N C9 C8 102.93(7) . . ? N C9 H9A 110.6(7) . . ? C8 C9 H9A 112.2(8) . . ? N C9 H9B 108.9(8) . . ? C8 C9 H9B 114.6(8) . . ? H9A C9 H9B 107.5(11) . . ? C11 C10 C5 113.51(8) . . ? C11 C10 H10A 108.8(9) . . ? C5 C10 H10A 109.4(8) . . ? C11 C10 H10B 108.5(8) . . ? C5 C10 H10B 109.2(8) . . ? H10A C10 H10B 107.3(11) . . ? C12 C11 C10 124.58(12) . . ? C12 C11 H11 119.7(9) . . ? C10 C11 H11 115.7(9) . . ? C11 C12 H12A 122.0(9) . . ? C11 C12 H12B 118.8(11) . . ? H12A C12 H12B 119.3(15) . . ? C8 C13 H13A 110.5(9) . . ? C8 C13 H13B 113.0(8) . . ? H13A C13 H13B 107.4(12) . . ? C8 C13 H13C 110.0(8) . . ? H13A C13 H13C 108.2(12) . . ? H13B C13 H13C 107.4(12) . . ? C8 C14 H14A 113.0(8) . . ? C8 C14 H14B 111.2(9) . . ? H14A C14 H14B 106.9(12) . . ? C8 C14 H14C 111.7(9) . . ? H14A C14 H14C 107.8(12) . . ? H14B C14 H14C 105.9(13) . . ? 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 C9 N C1 O1 12.07(14) . . . . ? C6 N C1 O1 171.80(9) . . . . ? C9 N C1 C2 -168.77(8) . . . . ? C6 N C1 C2 -9.03(14) . . . . ? O1 C1 C2 C3 120.73(10) . . . . ? N C1 C2 C3 -58.43(12) . . . . ? C1 C2 C3 C4 82.66(11) . . . . ? C2 C3 C4 C5 -66.44(12) . . . . ? C3 C4 C5 C6 58.36(12) . . . . ? C3 C4 C5 C10 179.57(9) . . . . ? C1 N C6 C5 67.72(12) . . . . ? C9 N C6 C5 -131.25(8) . . . . ? C1 N C6 C7 -168.02(9) . . . . ? C9 N C6 C7 -6.99(9) . . . . ? C4 C5 C6 N -70.82(10) . . . . ? C10 C5 C6 N 168.56(8) . . . . ? C4 C5 C6 C7 171.86(8) . . . . ? C10 C5 C6 C7 51.24(10) . . . . ? N C6 C7 O2 -85.71(8) . . . . ? C5 C6 C7 O2 39.69(10) . . . . ? N C6 C7 C8 31.93(8) . . . . ? C5 C6 C7 C8 157.33(7) . . . . ? O2 C7 C8 C14 -49.25(10) . . . . ? C6 C7 C8 C14 -164.95(8) . . . . ? O2 C7 C8 C9 71.11(9) . . . . ? C6 C7 C8 C9 -44.59(9) . . . . ? O2 C7 C8 C13 -172.59(8) . . . . ? C6 C7 C8 C13 71.70(9) . . . . ? C1 N C9 C8 141.85(8) . . . . ? C6 N C9 C8 -20.70(9) . . . . ? C14 C8 C9 N 159.29(8) . . . . ? C13 C8 C9 N -77.44(9) . . . . ? C7 C8 C9 N 39.17(9) . . . . ? C4 C5 C10 C11 59.23(11) . . . . ? C6 C5 C10 C11 -177.14(9) . . . . ? C5 C10 C11 C12 -119.98(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O1 0.882(16) 1.822(17) 2.6995(10) 173.5(15) 8_655 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.526 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.062