# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'JCS Perkin 1' loop_ _publ_author_name 'S.M. Allin' 'S.L. James' 'W.P. Martin' 'T.A.D. Smith' 'M.R.J. Elsegood' _publ_contact_author_name 'Dr Steven Allin' _publ_contact_author_address ; Dr Steven Allin Department of Chemistry Loughborough University Loughborough Leics LE11 3TU UK ; _publ_contact_author_email 'S.M.ALLIN@LBORO.AC.UK' _publ_section_title ; A facile and stereoselective synthesis of the pyrroloisoquinoline ring system. ; data_12 _database_code_CSD 166688 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 N O4' _chemical_formula_weight 277.31 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.3164(3) _cell_length_b 11.9673(7) _cell_length_c 20.8468(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1326.34(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5324 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 28.05 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11448 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.81 _reflns_number_total 3150 _reflns_number_gt 2853 _reflns_threshold_expression I>2\s(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 and local programs' _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^)+(0.0467P)^2^+0.2395P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom except OH coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(9) _refine_ls_number_reflns 3150 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3312(2) 0.42863(9) 0.05317(5) 0.0178(2) Uani 1 1 d . . . C1 C 0.2294(3) 0.32631(11) 0.06310(6) 0.0192(3) Uani 1 1 d . . . O1 O 0.0402(2) 0.28999(8) 0.03584(5) 0.0235(2) Uani 1 1 d . . . C2 C 0.3870(3) 0.26633(12) 0.11295(7) 0.0227(3) Uani 1 1 d . . . H2A H 0.4937 0.2083 0.0928 0.027 Uiso 1 1 calc R . . H2B H 0.2791 0.2309 0.1459 0.027 Uiso 1 1 calc R . . C3 C 0.5483(3) 0.35929(11) 0.14234(7) 0.0262(3) Uani 1 1 d . . . H3A H 0.7177 0.3312 0.1537 0.031 Uiso 1 1 calc R . . H3B H 0.4676 0.3905 0.1812 0.031 Uiso 1 1 calc R . . C4 C 0.5638(3) 0.44731(11) 0.08896(7) 0.0184(3) Uani 1 1 d . . . H4 H 0.7115 0.4311 0.0608 0.022 Uiso 1 1 calc R . . C5 C 0.5782(3) 0.56652(11) 0.11248(6) 0.0176(3) Uani 1 1 d . . . C6 C 0.7561(3) 0.59288(11) 0.16006(6) 0.0194(3) Uani 1 1 d . . . H6 H 0.8670 0.5364 0.1751 0.023 Uiso 1 1 calc R . . C7 C 0.7725(3) 0.69944(12) 0.18525(6) 0.0195(3) Uani 1 1 d . . . C8 C 0.6040(3) 0.78250(11) 0.16310(6) 0.0197(3) Uani 1 1 d . . . C9 C 0.4345(3) 0.75675(11) 0.11496(6) 0.0193(3) Uani 1 1 d . . . H9 H 0.3257 0.8134 0.0992 0.023 Uiso 1 1 calc R . . C10 C 0.4193(3) 0.64842(11) 0.08872(6) 0.0178(3) Uani 1 1 d . . . C11 C 0.2220(3) 0.62489(11) 0.03801(6) 0.0194(3) Uani 1 1 d . . . H11A H 0.2311 0.6838 0.0048 0.023 Uiso 1 1 calc R . . H11B H 0.0535 0.6292 0.0581 0.023 Uiso 1 1 calc R . . C12 C 0.2502(3) 0.51027(11) 0.00541(6) 0.0185(3) Uani 1 1 d . . . H12 H 0.0816 0.4870 -0.0112 0.022 Uiso 1 1 calc R . . C13 C 0.4335(3) 0.51352(11) -0.05097(6) 0.0218(3) Uani 1 1 d . . . H13A H 0.3913 0.5780 -0.0787 0.026 Uiso 1 1 calc R . . H13B H 0.6060 0.5251 -0.0343 0.026 Uiso 1 1 calc R . . O2 O 0.4292(3) 0.41521(9) -0.08822(5) 0.0308(3) Uani 1 1 d . . . H2 H 0.470(4) 0.3551(18) -0.0639(10) 0.046 Uiso 1 1 d . . . O3 O 0.9384(2) 0.73175(8) 0.23174(5) 0.0249(2) Uani 1 1 d . . . C14 C 1.1145(3) 0.64875(13) 0.25266(7) 0.0255(3) Uani 1 1 d . . . H14A H 1.0237 0.5870 0.2730 0.038 Uiso 1 1 calc R . . H14B H 1.2314 0.6820 0.2836 0.038 Uiso 1 1 calc R . . H14C H 1.2088 0.6206 0.2157 0.038 Uiso 1 1 calc R . . O4 O 0.6237(2) 0.88443(8) 0.19230(5) 0.0248(2) Uani 1 1 d . . . C15 C 0.4302(3) 0.96346(12) 0.17765(8) 0.0284(3) Uani 1 1 d . . . H15A H 0.4471 0.9878 0.1330 0.043 Uiso 1 1 calc R . . H15B H 0.4456 1.0282 0.2061 0.043 Uiso 1 1 calc R . . H15C H 0.2652 0.9285 0.1838 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0205(6) 0.0159(5) 0.0171(5) 0.0015(4) -0.0007(5) 0.0007(4) C1 0.0223(7) 0.0171(6) 0.0180(6) -0.0027(5) 0.0053(6) 0.0010(6) O1 0.0228(5) 0.0203(5) 0.0276(5) -0.0002(4) -0.0005(4) -0.0027(4) C2 0.0296(8) 0.0170(6) 0.0213(6) 0.0013(5) -0.0016(6) -0.0010(6) C3 0.0372(9) 0.0176(6) 0.0238(7) 0.0047(5) -0.0084(7) -0.0016(7) C4 0.0197(6) 0.0165(6) 0.0190(6) 0.0005(5) -0.0016(6) 0.0022(6) C5 0.0188(6) 0.0169(6) 0.0171(6) 0.0001(5) 0.0026(5) 0.0012(6) C6 0.0198(6) 0.0189(6) 0.0195(6) 0.0022(5) -0.0005(6) 0.0027(6) C7 0.0194(7) 0.0223(6) 0.0168(6) 0.0001(5) 0.0020(5) -0.0020(6) C8 0.0251(7) 0.0157(6) 0.0182(6) 0.0003(5) 0.0045(6) -0.0011(6) C9 0.0240(7) 0.0164(6) 0.0175(6) 0.0022(5) 0.0016(6) 0.0016(6) C10 0.0196(6) 0.0181(6) 0.0157(6) 0.0012(5) 0.0031(5) 0.0002(5) C11 0.0210(7) 0.0181(6) 0.0191(6) 0.0005(5) -0.0019(6) 0.0032(5) C12 0.0206(6) 0.0181(6) 0.0166(6) 0.0011(5) -0.0027(6) 0.0007(6) C13 0.0276(7) 0.0194(6) 0.0183(6) 0.0019(5) 0.0004(6) 0.0028(6) O2 0.0493(7) 0.0235(5) 0.0197(5) -0.0020(4) 0.0030(5) 0.0112(5) O3 0.0268(6) 0.0224(5) 0.0255(5) -0.0053(4) -0.0066(4) 0.0012(5) C14 0.0257(8) 0.0266(7) 0.0243(7) -0.0023(6) -0.0068(6) -0.0004(6) O4 0.0310(6) 0.0186(5) 0.0246(5) -0.0037(4) -0.0035(4) 0.0011(4) C15 0.0348(9) 0.0196(7) 0.0309(8) -0.0061(6) -0.0023(7) 0.0050(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3547(17) . ? N1 C12 1.4599(17) . ? N1 C4 1.4616(18) . ? C1 O1 1.2342(18) . ? C1 C2 1.516(2) . ? C2 C3 1.532(2) . ? C3 C4 1.5344(19) . ? C4 C5 1.5104(18) . ? C5 C10 1.3854(19) . ? C5 C6 1.4065(19) . ? C6 C7 1.3819(18) . ? C7 O3 1.3662(17) . ? C7 C8 1.416(2) . ? C8 O4 1.3673(16) . ? C8 C9 1.384(2) . ? C9 C10 1.4094(18) . ? C10 C11 1.5157(19) . ? C11 C12 1.5382(18) . ? C12 C13 1.527(2) . ? C13 O2 1.4099(17) . ? O3 C14 1.4327(18) . ? O4 C15 1.4305(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C12 126.25(12) . . ? C1 N1 C4 113.47(11) . . ? C12 N1 C4 119.69(11) . . ? O1 C1 N1 124.99(13) . . ? O1 C1 C2 126.83(12) . . ? N1 C1 C2 108.19(12) . . ? C1 C2 C3 103.86(11) . . ? C2 C3 C4 103.80(11) . . ? N1 C4 C5 110.67(11) . . ? N1 C4 C3 102.69(11) . . ? C5 C4 C3 114.57(11) . . ? C10 C5 C6 120.23(12) . . ? C10 C5 C4 121.42(12) . . ? C6 C5 C4 118.34(12) . . ? C7 C6 C5 121.16(12) . . ? O3 C7 C6 124.85(13) . . ? O3 C7 C8 116.19(12) . . ? C6 C7 C8 118.95(13) . . ? O4 C8 C9 124.86(13) . . ? O4 C8 C7 115.64(12) . . ? C9 C8 C7 119.50(12) . . ? C8 C9 C10 121.57(13) . . ? C5 C10 C9 118.50(13) . . ? C5 C10 C11 122.68(11) . . ? C9 C10 C11 118.76(12) . . ? C10 C11 C12 113.97(11) . . ? N1 C12 C13 110.72(11) . . ? N1 C12 C11 108.92(10) . . ? C13 C12 C11 112.31(11) . . ? O2 C13 C12 113.11(12) . . ? C7 O3 C14 116.20(11) . . ? C8 O4 C15 116.08(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 H2 O1 0.91(2) 1.87(2) 2.7516(15) 163.7(19) 4 _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.242 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.039 #===END data_7b _database_code_CSD 166689 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H17 N O2' _chemical_formula_weight 231.29 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.7150(6) _cell_length_b 8.0282(6) _cell_length_c 10.0287(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.876(2) _cell_angle_gamma 90.00 _cell_volume 584.15(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3799 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 28.66 _exptl_crystal_description prism _exptl_crystal_colour colurless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5096 _diffrn_reflns_av_R_equivalents 0.0124 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.68 _reflns_number_total 2514 _reflns_number_gt 2421 _reflns_threshold_expression I>2\s(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 and local programs' _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^)+(0.0453P)^2^+0.0876P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens 'geom except H2 coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.002(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(10) _refine_ls_number_reflns 2514 _refine_ls_number_parameters 159 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0807 _refine_ls_wR_factor_gt 0.0799 _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 N1 N 0.24956(13) 0.70624(13) 0.27653(10) 0.0212(2) Uani 1 1 d . . . C1 C 0.32797(17) 0.59837(18) 0.38252(13) 0.0262(3) Uani 1 1 d . . . O1 O 0.27310(13) 0.56125(15) 0.48069(10) 0.0356(3) Uani 1 1 d . . . C2 C 0.50022(18) 0.5279(2) 0.36292(15) 0.0324(3) Uani 1 1 d . . . H2A H 0.5077 0.4059 0.3780 0.039 Uiso 1 1 calc R . . H2B H 0.6124 0.5803 0.4297 0.039 Uiso 1 1 calc R . . C3 C 0.47837(18) 0.57073(18) 0.20967(14) 0.0279(3) Uani 1 1 d . . . H3A H 0.4195 0.4780 0.1451 0.033 Uiso 1 1 calc R . . H3B H 0.5993 0.5956 0.2000 0.033 Uiso 1 1 calc R . . C4 C 0.35341(16) 0.72670(17) 0.17765(12) 0.0217(2) Uani 1 1 d . . . C5 C 0.4686(2) 0.88690(19) 0.21378(15) 0.0298(3) Uani 1 1 d . . . H5A H 0.3867 0.9830 0.2028 0.045 Uiso 1 1 calc R . . H5B H 0.5396 0.8986 0.1497 0.045 Uiso 1 1 calc R . . H5C H 0.5533 0.8813 0.3119 0.045 Uiso 1 1 calc R . . C6 C 0.22147(16) 0.73251(17) 0.02563(12) 0.0215(2) Uani 1 1 d . . . C7 C 0.29466(18) 0.72629(18) -0.08430(14) 0.0271(3) Uani 1 1 d . . . H7 H 0.4241 0.7156 -0.0619 0.033 Uiso 1 1 calc R . . C8 C 0.1821(2) 0.7354(2) -0.22495(14) 0.0315(3) Uani 1 1 d . . . H8 H 0.2340 0.7293 -0.2982 0.038 Uiso 1 1 calc R . . C9 C -0.0064(2) 0.75352(18) -0.25845(13) 0.0310(3) Uani 1 1 d . . . H9 H -0.0844 0.7626 -0.3546 0.037 Uiso 1 1 calc R . . C10 C -0.08013(19) 0.75816(17) -0.15049(13) 0.0270(3) Uani 1 1 d . . . H10 H -0.2097 0.7691 -0.1739 0.032 Uiso 1 1 calc R . . C11 C 0.03093(17) 0.74712(16) -0.00781(13) 0.0222(2) Uani 1 1 d . . . C12 C -0.05501(17) 0.74967(19) 0.10718(13) 0.0253(3) Uani 1 1 d . . . H12A H -0.0989 0.6365 0.1186 0.030 Uiso 1 1 calc R . . H12B H -0.1629 0.8252 0.0787 0.030 Uiso 1 1 calc R . . C13 C 0.08274(17) 0.80795(16) 0.24838(13) 0.0221(3) Uani 1 1 d . . . H13 H 0.1174 0.9249 0.2340 0.027 Uiso 1 1 calc R . . C14 C 0.00148(19) 0.81283(18) 0.36711(14) 0.0257(3) Uani 1 1 d . . . H14A H 0.1002 0.8439 0.4564 0.031 Uiso 1 1 calc R . . H14B H -0.0936 0.9012 0.3456 0.031 Uiso 1 1 calc R . . O2 O -0.07879(14) 0.66110(14) 0.38893(11) 0.0300(2) Uani 1 1 d . . . H2 H 0.009(3) 0.601(3) 0.426(2) 0.045 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 N1 0.0192(5) 0.0268(6) 0.0190(5) -0.0008(4) 0.0084(4) -0.0004(4) C1 0.0219(6) 0.0329(7) 0.0210(6) 0.0019(5) 0.0036(5) 0.0011(5) O1 0.0319(5) 0.0519(7) 0.0248(5) 0.0122(5) 0.0119(4) 0.0084(5) C2 0.0240(6) 0.0408(8) 0.0317(7) 0.0064(6) 0.0088(5) 0.0073(6) C3 0.0230(6) 0.0317(7) 0.0309(7) 0.0011(6) 0.0117(5) 0.0037(5) C4 0.0211(5) 0.0259(6) 0.0212(5) -0.0014(5) 0.0109(5) -0.0014(5) C5 0.0279(7) 0.0323(7) 0.0322(7) -0.0066(6) 0.0141(6) -0.0093(6) C6 0.0270(6) 0.0181(5) 0.0212(5) -0.0002(5) 0.0106(5) -0.0012(5) C7 0.0313(6) 0.0265(7) 0.0284(6) -0.0021(6) 0.0167(5) -0.0035(5) C8 0.0487(8) 0.0291(7) 0.0239(6) -0.0016(6) 0.0215(6) -0.0047(7) C9 0.0466(8) 0.0268(7) 0.0178(6) 0.0002(5) 0.0085(5) -0.0012(6) C10 0.0307(6) 0.0265(7) 0.0224(6) 0.0006(5) 0.0073(5) 0.0021(5) C11 0.0276(6) 0.0211(6) 0.0192(5) -0.0001(5) 0.0098(5) 0.0013(5) C12 0.0203(5) 0.0355(7) 0.0205(5) 0.0018(6) 0.0075(4) 0.0039(5) C13 0.0235(6) 0.0234(6) 0.0223(6) 0.0005(5) 0.0114(5) 0.0023(5) C14 0.0267(6) 0.0302(7) 0.0237(6) -0.0025(5) 0.0131(5) 0.0004(5) O2 0.0274(5) 0.0363(6) 0.0287(5) 0.0042(4) 0.0129(4) -0.0015(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 N1 C1 1.3448(16) . ? N1 C13 1.4683(16) . ? N1 C4 1.4807(14) . ? C1 O1 1.2332(16) . ? C1 C2 1.5173(19) . ? C2 C3 1.5273(19) . ? C3 C4 1.5460(19) . ? C4 C6 1.5190(16) . ? C4 C5 1.5351(18) . ? C6 C11 1.3971(17) . ? C6 C7 1.4000(16) . ? C7 C8 1.3843(19) . ? C8 C9 1.385(2) . ? C9 C10 1.3842(18) . ? C10 C11 1.3985(18) . ? C11 C12 1.5132(15) . ? C12 C13 1.5265(18) . ? C13 C14 1.5232(16) . ? C14 O2 1.4168(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C13 129.75(10) . . ? C1 N1 C4 113.60(10) . . ? C13 N1 C4 116.62(9) . . ? O1 C1 N1 127.04(12) . . ? O1 C1 C2 124.53(12) . . ? N1 C1 C2 108.43(11) . . ? C1 C2 C3 104.16(11) . . ? C2 C3 C4 103.83(10) . . ? N1 C4 C6 110.18(9) . . ? N1 C4 C5 109.67(10) . . ? C6 C4 C5 110.36(11) . . ? N1 C4 C3 102.25(10) . . ? C6 C4 C3 113.02(10) . . ? C5 C4 C3 111.06(10) . . ? C11 C6 C7 119.16(11) . . ? C11 C6 C4 122.33(10) . . ? C7 C6 C4 118.50(10) . . ? C8 C7 C6 121.29(12) . . ? C7 C8 C9 119.74(12) . . ? C10 C9 C8 119.35(12) . . ? C9 C10 C11 121.80(12) . . ? C6 C11 C10 118.65(11) . . ? C6 C11 C12 121.07(10) . . ? C10 C11 C12 120.27(11) . . ? C11 C12 C13 111.34(10) . . ? N1 C13 C14 115.52(10) . . ? N1 C13 C12 107.23(10) . . ? C14 C13 C12 113.04(10) . . ? O2 C14 C13 114.60(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 H2 O1 0.81(2) 1.95(2) 2.6759(14) 149(2) . _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.264 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.034 #===END data_13b _database_code_CSD 172096 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 N O4' _chemical_formula_weight 291.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.5447(10) _cell_length_b 9.5411(9) _cell_length_c 14.7057(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.006(2) _cell_angle_gamma 90.00 _cell_volume 1475.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5288 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.86 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12656 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.80 _reflns_number_total 6544 _reflns_number_gt 5287 _reflns_threshold_expression I>2\s(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 and local programs' _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^)+(0.0419P)^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 except OH coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0015(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(6) _refine_ls_number_reflns 6544 _refine_ls_number_parameters 392 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0786 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.10352(12) 0.18627(14) 1.19232(8) 0.0237(3) Uani 1 1 d . . . C1 C -0.23212(15) 0.18916(19) 1.18402(11) 0.0297(4) Uani 1 1 d . . . O1 O -0.30373(11) 0.23134(14) 1.24075(8) 0.0399(3) Uani 1 1 d . . . C2 C -0.27624(17) 0.1291(2) 1.09195(12) 0.0357(4) Uani 1 1 d . . . H2A H -0.3421 0.1894 1.0606 0.043 Uiso 1 1 calc R . . H2B H -0.3111 0.0335 1.0982 0.043 Uiso 1 1 calc R . . C3 C -0.15634(16) 0.1263(2) 1.04028(12) 0.0328(4) Uani 1 1 d . . . H3A H -0.1471 0.2143 1.0057 0.039 Uiso 1 1 calc R . . H3B H -0.1575 0.0462 0.9975 0.039 Uiso 1 1 calc R . . C4 C -0.04868(16) 0.11069(17) 1.11545(11) 0.0255(4) Uani 1 1 d . . . C5 C -0.02602(18) -0.04395(18) 1.14232(13) 0.0364(4) Uani 1 1 d . . . H5A H -0.1062 -0.0861 1.1583 0.055 Uiso 1 1 calc R . . H5B H 0.0364 -0.0491 1.1948 0.055 Uiso 1 1 calc R . . H5C H 0.0062 -0.0950 1.0909 0.055 Uiso 1 1 calc R . . C6 C 0.07375(14) 0.17863(17) 1.09123(10) 0.0227(3) Uani 1 1 d . . . C7 C 0.12371(16) 0.14328(17) 1.00812(11) 0.0260(4) Uani 1 1 d . . . H7 H 0.0798 0.0777 0.9688 0.031 Uiso 1 1 calc R . . C8 C 0.23546(15) 0.20221(17) 0.98271(10) 0.0258(4) Uani 1 1 d . . . C9 C 0.30164(14) 0.29711(17) 1.04229(11) 0.0255(3) Uani 1 1 d . . . C10 C 0.25202(15) 0.33261(17) 1.12339(11) 0.0262(4) Uani 1 1 d . . . H10 H 0.2959 0.3981 1.1628 0.031 Uiso 1 1 calc R . . C11 C 0.13799(14) 0.27376(17) 1.14870(10) 0.0241(3) Uani 1 1 d . . . O2 O 0.28910(10) 0.17839(13) 0.90136(8) 0.0321(3) Uani 1 1 d . . . C12 C 0.22197(19) 0.0875(2) 0.83805(13) 0.0421(5) Uani 1 1 d . . . H12A H 0.1383 0.1275 0.8204 0.063 Uiso 1 1 calc R . . H12B H 0.2113 -0.0044 0.8664 0.063 Uiso 1 1 calc R . . H12C H 0.2701 0.0767 0.7839 0.063 Uiso 1 1 calc R . . O3 O 0.41277(10) 0.34965(12) 1.01263(8) 0.0316(3) Uani 1 1 d . . . C13 C 0.47898(17) 0.4499(2) 1.07141(13) 0.0401(5) Uani 1 1 d . . . H13A H 0.5104 0.4036 1.1281 0.060 Uiso 1 1 calc R . . H13B H 0.4208 0.5258 1.0854 0.060 Uiso 1 1 calc R . . H13C H 0.5508 0.4886 1.0408 0.060 Uiso 1 1 calc R . . C14 C 0.08696(15) 0.31959(18) 1.23733(11) 0.0292(4) Uani 1 1 d . . . H14A H 0.0525 0.4157 1.2296 0.035 Uiso 1 1 calc R . . H14B H 0.1583 0.3234 1.2847 0.035 Uiso 1 1 calc R . . C15 C -0.01617(15) 0.22542(17) 1.27076(10) 0.0264(4) Uani 1 1 d . . . H15 H 0.0251 0.1380 1.2960 0.032 Uiso 1 1 calc R . . C16 C -0.07829(16) 0.29956(19) 1.34778(11) 0.0329(4) Uani 1 1 d . . . H16A H -0.0107 0.3390 1.3904 0.039 Uiso 1 1 calc R . . H16B H -0.1295 0.3789 1.3219 0.039 Uiso 1 1 calc R . . O4 O -0.15734(14) 0.21307(15) 1.39729(9) 0.0450(4) Uani 1 1 d . . . H4 H -0.226(2) 0.207(3) 1.3535(16) 0.067 Uiso 1 1 d . . . N1A N 0.31432(12) -0.17032(14) 0.28429(9) 0.0258(3) Uani 1 1 d . . . C1A C 0.29683(16) -0.22294(19) 0.19934(11) 0.0312(4) Uani 1 1 d . . . O1A O 0.23305(13) -0.32645(14) 0.17529(9) 0.0453(3) Uani 1 1 d . . . C2A C 0.36817(18) -0.1334(2) 0.13612(12) 0.0368(4) Uani 1 1 d . . . H2A1 H 0.3156 -0.1134 0.0792 0.044 Uiso 1 1 calc R . . H2A2 H 0.4478 -0.1798 0.1206 0.044 Uiso 1 1 calc R . . C3A C 0.39619(17) -0.00005(19) 0.19002(11) 0.0311(4) Uani 1 1 d . . . H3A1 H 0.3276 0.0697 0.1781 0.037 Uiso 1 1 calc R . . H3A2 H 0.4779 0.0417 0.1745 0.037 Uiso 1 1 calc R . . C4A C 0.40302(15) -0.04874(17) 0.28992(11) 0.0253(4) Uani 1 1 d . . . C5A C 0.53721(16) -0.1000(2) 0.32111(13) 0.0372(4) Uani 1 1 d . . . H5A1 H 0.5659 -0.1679 0.2769 0.056 Uiso 1 1 calc R . . H5A2 H 0.5356 -0.1448 0.3810 0.056 Uiso 1 1 calc R . . H5A3 H 0.5957 -0.0201 0.3253 0.056 Uiso 1 1 calc R . . C6A C 0.35761(15) 0.06153(17) 0.35486(11) 0.0241(4) Uani 1 1 d . . . C7A C 0.41877(15) 0.19288(18) 0.35953(11) 0.0274(4) Uani 1 1 d . . . H7A H 0.4880 0.2099 0.3230 0.033 Uiso 1 1 calc R . . C8A C 0.37981(15) 0.29678(18) 0.41612(11) 0.0272(4) Uani 1 1 d . . . C9A C 0.27675(15) 0.27265(18) 0.46957(11) 0.0269(4) Uani 1 1 d . . . C10A C 0.21745(15) 0.14351(18) 0.46566(11) 0.0270(4) Uani 1 1 d . . . H10A H 0.1484 0.1265 0.5024 0.032 Uiso 1 1 calc R . . C11A C 0.25712(15) 0.03737(17) 0.40864(11) 0.0246(4) Uani 1 1 d . . . O2A O 0.43345(11) 0.42785(13) 0.42593(8) 0.0364(3) Uani 1 1 d . . . C12A C 0.54014(18) 0.4564(2) 0.37576(14) 0.0462(5) Uani 1 1 d . . . H12D H 0.5153 0.4510 0.3104 0.069 Uiso 1 1 calc R . . H12E H 0.6070 0.3874 0.3914 0.069 Uiso 1 1 calc R . . H12F H 0.5721 0.5507 0.3907 0.069 Uiso 1 1 calc R . . O3A O 0.24168(11) 0.38238(13) 0.52207(8) 0.0336(3) Uani 1 1 d . . . C13A C 0.15115(18) 0.3534(2) 0.58651(14) 0.0457(5) Uani 1 1 d . . . H13D H 0.1848 0.2812 0.6291 0.068 Uiso 1 1 calc R . . H13E H 0.0722 0.3199 0.5547 0.068 Uiso 1 1 calc R . . H13F H 0.1340 0.4390 0.6203 0.068 Uiso 1 1 calc R . . C14A C 0.18772(16) -0.10090(18) 0.40691(11) 0.0276(4) Uani 1 1 d . . . H14C H 0.1068 -0.0911 0.3691 0.033 Uiso 1 1 calc R . . H14D H 0.1667 -0.1246 0.4696 0.033 Uiso 1 1 calc R . . C15A C 0.26364(15) -0.21982(19) 0.36965(11) 0.0278(4) Uani 1 1 d . . . H15A H 0.3378 -0.2378 0.4143 0.033 Uiso 1 1 calc R . . C16A C 0.18524(17) -0.35414(19) 0.36174(13) 0.0363(4) Uani 1 1 d . . . H16C H 0.2367 -0.4289 0.3356 0.044 Uiso 1 1 calc R . . H16D H 0.1648 -0.3844 0.4234 0.044 Uiso 1 1 calc R . . O4A O 0.06961(12) -0.33747(14) 0.30604(10) 0.0433(3) Uani 1 1 d . . . H4A H 0.097(2) -0.328(3) 0.2512(15) 0.065 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 N1 0.0255(7) 0.0216(7) 0.0241(7) -0.0030(6) 0.0013(5) -0.0010(6) C1 0.0285(9) 0.0284(9) 0.0326(9) 0.0015(8) 0.0040(7) -0.0049(8) O1 0.0302(6) 0.0498(8) 0.0405(7) -0.0074(6) 0.0093(6) -0.0014(6) C2 0.0282(9) 0.0440(11) 0.0347(10) -0.0023(9) 0.0009(7) -0.0082(8) C3 0.0308(9) 0.0408(10) 0.0263(9) -0.0038(8) -0.0008(7) -0.0087(8) C4 0.0302(9) 0.0230(9) 0.0232(8) -0.0032(7) 0.0017(7) -0.0024(7) C5 0.0450(11) 0.0257(10) 0.0393(10) -0.0026(8) 0.0085(9) -0.0002(8) C6 0.0251(8) 0.0200(8) 0.0226(8) 0.0016(7) -0.0009(6) 0.0034(7) C7 0.0296(9) 0.0229(8) 0.0249(8) -0.0039(7) -0.0028(7) 0.0020(7) C8 0.0276(8) 0.0251(9) 0.0245(8) 0.0017(7) 0.0017(7) 0.0084(7) C9 0.0239(8) 0.0221(8) 0.0303(9) 0.0045(7) 0.0003(7) 0.0021(7) C10 0.0278(9) 0.0228(8) 0.0273(8) -0.0015(7) -0.0041(7) 0.0007(7) C11 0.0270(8) 0.0219(8) 0.0230(8) 0.0000(7) -0.0020(6) 0.0028(7) O2 0.0300(6) 0.0384(7) 0.0282(6) -0.0054(5) 0.0038(5) 0.0019(6) C12 0.0424(11) 0.0497(13) 0.0344(10) -0.0125(9) 0.0049(9) 0.0004(9) O3 0.0279(6) 0.0336(7) 0.0336(7) -0.0024(5) 0.0041(5) -0.0052(5) C13 0.0334(10) 0.0417(12) 0.0453(11) -0.0044(9) 0.0032(8) -0.0118(9) C14 0.0292(8) 0.0307(9) 0.0272(9) -0.0060(7) -0.0020(7) 0.0002(7) C15 0.0302(9) 0.0269(9) 0.0216(8) 0.0000(7) -0.0013(7) 0.0016(7) C16 0.0367(9) 0.0355(10) 0.0267(9) -0.0055(8) 0.0043(7) -0.0010(8) O4 0.0559(9) 0.0484(9) 0.0322(7) 0.0015(7) 0.0136(6) -0.0040(7) N1A 0.0256(7) 0.0243(7) 0.0273(7) 0.0000(6) 0.0004(6) 0.0005(6) C1A 0.0360(9) 0.0286(9) 0.0287(9) -0.0042(8) -0.0009(7) 0.0067(8) O1A 0.0647(9) 0.0343(8) 0.0363(7) -0.0094(6) 0.0005(6) -0.0091(7) C2A 0.0439(11) 0.0379(11) 0.0295(9) -0.0037(8) 0.0084(8) 0.0061(9) C3A 0.0318(9) 0.0321(10) 0.0302(9) 0.0009(8) 0.0076(7) -0.0005(8) C4A 0.0228(8) 0.0244(9) 0.0289(9) 0.0000(7) 0.0025(7) -0.0001(7) C5A 0.0279(9) 0.0391(11) 0.0440(11) -0.0011(9) -0.0002(8) 0.0053(8) C6A 0.0231(8) 0.0249(9) 0.0238(8) 0.0008(7) -0.0020(7) 0.0023(7) C7A 0.0210(8) 0.0316(9) 0.0297(9) -0.0010(7) 0.0021(7) -0.0033(7) C8A 0.0248(8) 0.0257(9) 0.0303(9) 0.0000(7) -0.0037(7) -0.0032(7) C9A 0.0269(8) 0.0298(9) 0.0237(8) -0.0046(7) -0.0018(7) 0.0048(7) C10A 0.0230(8) 0.0336(10) 0.0243(8) 0.0016(7) 0.0013(7) -0.0007(7) C11A 0.0243(9) 0.0274(9) 0.0217(8) -0.0001(7) -0.0020(7) -0.0022(7) O2A 0.0328(6) 0.0307(7) 0.0462(7) -0.0088(6) 0.0055(6) -0.0080(6) C12A 0.0407(11) 0.0392(12) 0.0596(13) -0.0076(10) 0.0107(10) -0.0168(9) O3A 0.0335(6) 0.0326(7) 0.0350(7) -0.0071(5) 0.0050(5) 0.0009(6) C13A 0.0376(11) 0.0497(13) 0.0510(12) -0.0181(10) 0.0129(9) -0.0020(9) C14A 0.0305(9) 0.0275(9) 0.0253(8) 0.0027(7) 0.0052(7) -0.0033(7) C15A 0.0303(8) 0.0269(9) 0.0255(8) 0.0042(7) -0.0024(7) -0.0022(7) C16A 0.0403(10) 0.0283(10) 0.0406(11) 0.0004(8) 0.0031(8) -0.0048(8) O4A 0.0359(7) 0.0368(8) 0.0566(8) -0.0074(7) -0.0025(6) -0.0072(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 N1 C1 1.353(2) . ? N1 C15 1.4731(19) . ? N1 C4 1.491(2) . ? C1 O1 1.2313(19) . ? C1 C2 1.513(2) . ? C2 C3 1.520(2) . ? C3 C4 1.535(2) . ? C4 C6 1.509(2) . ? C4 C5 1.542(2) . ? C6 C11 1.385(2) . ? C6 C7 1.405(2) . ? C7 C8 1.381(2) . ? C8 O2 1.3774(19) . ? C8 C9 1.410(2) . ? C9 O3 1.3734(18) . ? C9 C10 1.378(2) . ? C10 C11 1.401(2) . ? C11 C14 1.509(2) . ? O2 C12 1.424(2) . ? O3 C13 1.437(2) . ? C14 C15 1.519(2) . ? C15 C16 1.522(2) . ? C16 O4 1.411(2) . ? N1A C1A 1.347(2) . ? N1A C15A 1.476(2) . ? N1A C4A 1.489(2) . ? C1A O1A 1.233(2) . ? C1A C2A 1.503(3) . ? C2A C3A 1.517(3) . ? C3A C4A 1.538(2) . ? C4A C6A 1.520(2) . ? C4A C5A 1.537(2) . ? C6A C11A 1.385(2) . ? C6A C7A 1.409(2) . ? C7A C8A 1.375(2) . ? C8A O2A 1.376(2) . ? C8A C9A 1.404(2) . ? C9A O3A 1.3671(19) . ? C9A C10A 1.381(2) . ? C10A C11A 1.397(2) . ? C11A C14A 1.508(2) . ? O2A C12A 1.414(2) . ? O3A C13A 1.419(2) . ? C14A C15A 1.513(2) . ? C15A C16A 1.525(2) . ? C16A O4A 1.429(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C15 129.29(13) . . ? C1 N1 C4 112.37(13) . . ? C15 N1 C4 117.50(12) . . ? O1 C1 N1 127.12(15) . . ? O1 C1 C2 124.42(15) . . ? N1 C1 C2 108.45(14) . . ? C1 C2 C3 103.85(13) . . ? C2 C3 C4 103.93(13) . . ? N1 C4 C6 110.77(13) . . ? N1 C4 C3 101.09(13) . . ? C6 C4 C3 112.95(13) . . ? N1 C4 C5 109.26(13) . . ? C6 C4 C5 110.59(14) . . ? C3 C4 C5 111.78(15) . . ? C11 C6 C7 119.42(14) . . ? C11 C6 C4 121.84(14) . . ? C7 C6 C4 118.75(14) . . ? C8 C7 C6 121.11(15) . . ? O2 C8 C7 125.31(15) . . ? O2 C8 C9 115.48(14) . . ? C7 C8 C9 119.20(14) . . ? O3 C9 C10 124.70(15) . . ? O3 C9 C8 115.67(14) . . ? C10 C9 C8 119.63(15) . . ? C9 C10 C11 121.09(15) . . ? C6 C11 C10 119.53(14) . . ? C6 C11 C14 121.90(14) . . ? C10 C11 C14 118.55(14) . . ? C8 O2 C12 116.92(13) . . ? C9 O3 C13 116.19(13) . . ? C11 C14 C15 114.50(13) . . ? N1 C15 C14 108.62(12) . . ? N1 C15 C16 114.99(13) . . ? C14 C15 C16 108.73(13) . . ? O4 C16 C15 114.38(14) . . ? C1A N1A C15A 129.44(14) . . ? C1A N1A C4A 112.76(13) . . ? C15A N1A C4A 117.74(13) . . ? O1A C1A N1A 126.96(17) . . ? O1A C1A C2A 124.38(16) . . ? N1A C1A C2A 108.65(15) . . ? C1A C2A C3A 103.96(14) . . ? C2A C3A C4A 103.90(14) . . ? N1A C4A C6A 110.48(12) . . ? N1A C4A C5A 109.30(13) . . ? C6A C4A C5A 110.90(13) . . ? N1A C4A C3A 101.24(12) . . ? C6A C4A C3A 113.28(13) . . ? C5A C4A C3A 111.22(14) . . ? C11A C6A C7A 119.08(15) . . ? C11A C6A C4A 122.04(14) . . ? C7A C6A C4A 118.88(14) . . ? C8A C7A C6A 121.03(15) . . ? C7A C8A O2A 125.48(14) . . ? C7A C8A C9A 119.75(15) . . ? O2A C8A C9A 114.77(14) . . ? O3A C9A C10A 124.55(14) . . ? O3A C9A C8A 116.18(14) . . ? C10A C9A C8A 119.27(15) . . ? C9A C10A C11A 121.19(15) . . ? C6A C11A C10A 119.67(15) . . ? C6A C11A C14A 121.71(14) . . ? C10A C11A C14A 118.62(14) . . ? C8A O2A C12A 117.17(14) . . ? C9A O3A C13A 116.69(14) . . ? C11A C14A C15A 113.19(13) . . ? N1A C15A C14A 107.47(13) . . ? N1A C15A C16A 115.51(14) . . ? C14A C15A C16A 111.10(13) . . ? O4A C16A C15A 112.72(14) . . ? 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 C15 N1 C1 O1 3.1(3) . . . . ? C4 N1 C1 O1 172.27(17) . . . . ? C15 N1 C1 C2 -176.19(16) . . . . ? C4 N1 C1 C2 -7.02(19) . . . . ? O1 C1 C2 C3 166.83(17) . . . . ? N1 C1 C2 C3 -13.86(19) . . . . ? C1 C2 C3 C4 28.19(19) . . . . ? C1 N1 C4 C6 144.42(14) . . . . ? C15 N1 C4 C6 -45.02(18) . . . . ? C1 N1 C4 C3 24.46(17) . . . . ? C15 N1 C4 C3 -164.97(13) . . . . ? C1 N1 C4 C5 -93.51(16) . . . . ? C15 N1 C4 C5 77.06(17) . . . . ? C2 C3 C4 N1 -31.30(17) . . . . ? C2 C3 C4 C6 -149.69(15) . . . . ? C2 C3 C4 C5 84.82(17) . . . . ? N1 C4 C6 C11 14.9(2) . . . . ? C3 C4 C6 C11 127.44(16) . . . . ? C5 C4 C6 C11 -106.43(17) . . . . ? N1 C4 C6 C7 -165.48(13) . . . . ? C3 C4 C6 C7 -52.9(2) . . . . ? C5 C4 C6 C7 73.23(18) . . . . ? C11 C6 C7 C8 -0.2(2) . . . . ? C4 C6 C7 C8 -179.91(15) . . . . ? C6 C7 C8 O2 -177.33(14) . . . . ? C6 C7 C8 C9 1.4(2) . . . . ? O2 C8 C9 O3 -2.0(2) . . . . ? C7 C8 C9 O3 179.15(14) . . . . ? O2 C8 C9 C10 176.92(14) . . . . ? C7 C8 C9 C10 -1.9(2) . . . . ? O3 C9 C10 C11 -179.83(14) . . . . ? C8 C9 C10 C11 1.3(2) . . . . ? C7 C6 C11 C10 -0.4(2) . . . . ? C4 C6 C11 C10 179.30(15) . . . . ? C7 C6 C11 C14 177.91(14) . . . . ? C4 C6 C11 C14 -2.4(2) . . . . ? C9 C10 C11 C6 -0.2(2) . . . . ? C9 C10 C11 C14 -178.53(14) . . . . ? C7 C8 O2 C12 1.2(2) . . . . ? C9 C8 O2 C12 -177.54(14) . . . . ? C10 C9 O3 C13 -0.8(2) . . . . ? C8 C9 O3 C13 178.08(14) . . . . ? C6 C11 C14 C15 16.6(2) . . . . ? C10 C11 C14 C15 -165.08(14) . . . . ? C1 N1 C15 C14 -132.15(17) . . . . ? C4 N1 C15 C14 59.14(17) . . . . ? C1 N1 C15 C16 -10.1(2) . . . . ? C4 N1 C15 C16 -178.79(14) . . . . ? C11 C14 C15 N1 -41.99(18) . . . . ? C11 C14 C15 C16 -167.79(14) . . . . ? N1 C15 C16 O4 70.30(19) . . . . ? C14 C15 C16 O4 -167.69(14) . . . . ? C15A N1A C1A O1A -0.1(3) . . . . ? C4A N1A C1A O1A 176.80(16) . . . . ? C15A N1A C1A C2A 179.51(15) . . . . ? C4A N1A C1A C2A -3.57(19) . . . . ? O1A C1A C2A C3A 163.53(17) . . . . ? N1A C1A C2A C3A -16.12(19) . . . . ? C1A C2A C3A C4A 28.39(18) . . . . ? C1A N1A C4A C6A 141.52(14) . . . . ? C15A N1A C4A C6A -41.17(17) . . . . ? C1A N1A C4A C5A -96.19(16) . . . . ? C15A N1A C4A C5A 81.12(17) . . . . ? C1A N1A C4A C3A 21.24(16) . . . . ? C15A N1A C4A C3A -161.45(14) . . . . ? C2A C3A C4A N1A -29.58(16) . . . . ? C2A C3A C4A C6A -147.86(14) . . . . ? C2A C3A C4A C5A 86.43(17) . . . . ? N1A C4A C6A C11A 8.1(2) . . . . ? C5A C4A C6A C11A -113.25(17) . . . . ? C3A C4A C6A C11A 120.87(16) . . . . ? N1A C4A C6A C7A -171.11(13) . . . . ? C5A C4A C6A C7A 67.54(19) . . . . ? C3A C4A C6A C7A -58.34(19) . . . . ? C11A C6A C7A C8A -0.3(2) . . . . ? C4A C6A C7A C8A 178.94(14) . . . . ? C6A C7A C8A O2A 179.65(15) . . . . ? C6A C7A C8A C9A -0.6(2) . . . . ? C7A C8A C9A O3A -178.25(14) . . . . ? O2A C8A C9A O3A 1.51(19) . . . . ? C7A C8A C9A C10A 1.2(2) . . . . ? O2A C8A C9A C10A -179.06(14) . . . . ? O3A C9A C10A C11A 178.53(15) . . . . ? C8A C9A C10A C11A -0.9(2) . . . . ? C7A C6A C11A C10A 0.6(2) . . . . ? C4A C6A C11A C10A -178.58(14) . . . . ? C7A C6A C11A C14A -179.95(14) . . . . ? C4A C6A C11A C14A 0.8(2) . . . . ? C9A C10A C11A C6A -0.1(2) . . . . ? C9A C10A C11A C14A -179.49(14) . . . . ? C7A C8A O2A C12A -2.1(2) . . . . ? C9A C8A O2A C12A 178.12(15) . . . . ? C10A C9A O3A C13A 9.9(2) . . . . ? C8A C9A O3A C13A -170.65(14) . . . . ? C6A C11A C14A C15A 20.2(2) . . . . ? C10A C11A C14A C15A -160.41(14) . . . . ? C1A N1A C15A C14A -121.32(18) . . . . ? C4A N1A C15A C14A 61.89(16) . . . . ? C1A N1A C15A C16A 3.3(2) . . . . ? C4A N1A C15A C16A -173.48(14) . . . . ? C11A C14A C15A N1A -47.90(17) . . . . ? C11A C14A C15A C16A -175.15(14) . . . . ? N1A C15A C16A O4A -65.6(2) . . . . ? C14A C15A C16A O4A 57.2(2) . . . . ? 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 O4 H4 O1 0.94(2) 1.81(2) 2.6863(19) 154(2) . O4A H4A O1A 0.88(2) 1.88(2) 2.6723(19) 149(2) . _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.208 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.035 #===END