Supplementary Material (ESI) for Analyst This journal is (C) The Royal Society of Chemistry 2007 data_global _journal_name_full 'The Analyst' _journal_coden_cambridge 0091 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name I.Nicholls B.Karlsson B.Mizaikoff J.O'Mahony _publ_contact_author_name 'Prof Ian A. Nicholls' _publ_contact_author_email IAN.NICHOLLS@HIK.SE data_jmm01 _database_code_depnum_ccdc_archive 'CCDC 656232' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 N O3' _chemical_formula_weight 309.35 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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 9.5594(12) _cell_length_b 5.8786(7) _cell_length_c 29.704(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.345(2) _cell_angle_gamma 90.00 _cell_volume 1659.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6153 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 22.19 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8914 _exptl_absorpt_correction_T_max 0.9834 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '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_% ? _diffrn_reflns_number 21891 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 24.00 _reflns_number_total 2886 _reflns_number_gt 2505 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0940P)^2^+0.4359P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2886 _refine_ls_number_parameters 419 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1628 _refine_ls_wR_factor_gt 0.1493 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 C1 C 0.6742(4) 0.0453(8) 1.00548(12) 0.0625(10) Uani 1 1 d . . . H1 H 0.6212 -0.0877 1.0040 0.075 Uiso 1 1 calc R . . C2 C 0.6794(4) 0.1793(9) 1.04283(14) 0.0664(11) Uani 1 1 d . . . O1 O 0.6084(3) 0.1422(7) 1.07980(10) 0.0786(9) Uani 1 1 d . . . C11 C 0.5169(5) -0.0480(10) 1.07817(16) 0.0859(14) Uani 1 1 d . . . H11A H 0.4503 -0.0385 1.0516 0.129 Uiso 1 1 calc R . . H11B H 0.4677 -0.0490 1.1046 0.129 Uiso 1 1 calc R . . H11C H 0.5708 -0.1854 1.0772 0.129 Uiso 1 1 calc R . . C3 C 0.7641(5) 0.3764(9) 1.04536(16) 0.0800(13) Uani 1 1 d . . . H3 H 0.7701 0.4656 1.0714 0.096 Uiso 1 1 calc R . . C4 C 0.8370(4) 0.4386(9) 1.01057(15) 0.0771(12) Uani 1 1 d . . . H4 H 0.8922 0.5691 1.0131 0.093 Uiso 1 1 calc R . . C5 C 0.8298(4) 0.3084(7) 0.97097(14) 0.0603(10) Uani 1 1 d . . . C6 C 0.8971(4) 0.3736(8) 0.93275(14) 0.0660(10) Uani 1 1 d . . . H6 H 0.9513 0.5053 0.9344 0.079 Uiso 1 1 calc R . . C7 C 0.8848(4) 0.2497(8) 0.89374(14) 0.0643(11) Uani 1 1 d . . . C12 C 0.9511(4) 0.3229(9) 0.85175(15) 0.0738(12) Uani 1 1 d . . . H12 H 0.9498 0.1895 0.8319 0.089 Uiso 1 1 calc R . . C13 C 1.1034(5) 0.3939(17) 0.86192(19) 0.126(3) Uani 1 1 d . . . H13A H 1.1422 0.4238 0.8341 0.189 Uiso 1 1 calc R . . H13B H 1.1557 0.2739 0.8780 0.189 Uiso 1 1 calc R . . H13C H 1.1091 0.5289 0.8802 0.189 Uiso 1 1 calc R . . C14 C 0.8630(5) 0.5009(9) 0.82632(15) 0.0781(12) Uani 1 1 d . . . O2 O 0.7356(4) 0.5235(9) 0.82807(16) 0.1302(17) Uani 1 1 d . . . O3 O 0.9226(4) 0.6286(10) 0.80121(16) 0.147(2) Uani 1 1 d . . . C8 C 0.8067(5) 0.0467(8) 0.89261(15) 0.0737(12) Uani 1 1 d . . . H8 H 0.7992 -0.0418 0.8665 0.088 Uiso 1 1 calc R . . C9 C 0.7419(4) -0.0237(8) 0.92853(13) 0.0712(11) Uani 1 1 d . . . H9 H 0.6920 -0.1598 0.9268 0.085 Uiso 1 1 calc R . . C10 C 0.7494(4) 0.1066(7) 0.96847(13) 0.0568(9) Uani 1 1 d . . . C15 C 0.3150(4) 0.9768(8) 0.48891(12) 0.0612(10) Uani 1 1 d . . . H15 H 0.3644 1.1124 0.4939 0.073 Uiso 1 1 calc R . . C16 C 0.3148(4) 0.8666(9) 0.44801(13) 0.0669(11) Uani 1 1 d . . . O4 O 0.3838(3) 0.9338(7) 0.41286(10) 0.0880(10) Uani 1 1 d . . . C25 C 0.4838(5) 1.1112(11) 0.42071(17) 0.0908(16) Uani 1 1 d . . . H25A H 0.4358 1.2523 0.4244 0.136 Uiso 1 1 calc R . . H25B H 0.5376 1.1228 0.3954 0.136 Uiso 1 1 calc R . . H25C H 0.5456 1.0788 0.4476 0.136 Uiso 1 1 calc R . . C17 C 0.2368(4) 0.6649(9) 0.44035(14) 0.0698(11) Uani 1 1 d . . . H17 H 0.2344 0.5924 0.4124 0.084 Uiso 1 1 calc R . . C18 C 0.1649(4) 0.5741(8) 0.47290(13) 0.0643(11) Uani 1 1 d . . . H18 H 0.1140 0.4405 0.4670 0.077 Uiso 1 1 calc R . . C19 C 0.1664(3) 0.6796(7) 0.51535(12) 0.0535(9) Uani 1 1 d . . . C20 C 0.0993(4) 0.5816(7) 0.55090(13) 0.0604(10) Uani 1 1 d . . . H20 H 0.0508 0.4453 0.5457 0.072 Uiso 1 1 calc R . . C21 C 0.1034(4) 0.6813(7) 0.59285(13) 0.0582(10) Uani 1 1 d . . . C26 C 0.0335(4) 0.5672(9) 0.63011(13) 0.0679(11) Uani 1 1 d . . . H26 H -0.0231 0.4419 0.6160 0.082 Uiso 1 1 calc R . . C27 C -0.0669(5) 0.7227(12) 0.6521(2) 0.108(2) Uani 1 1 d . . . H27A H -0.0155 0.8493 0.6661 0.162 Uiso 1 1 calc R . . H27B H -0.1102 0.6394 0.6747 0.162 Uiso 1 1 calc R . . H27C H -0.1383 0.7775 0.6294 0.162 Uiso 1 1 calc R . . C28 C 0.1378(4) 0.4635(8) 0.66590(14) 0.0668(11) Uani 1 1 d . . . O5 O 0.0820(3) 0.3130(8) 0.69032(11) 0.1010(12) Uani 1 1 d . . . O6 O 0.2597(4) 0.5052(10) 0.67113(13) 0.1284(18) Uani 1 1 d . . . C22 C 0.1761(4) 0.8892(8) 0.59954(13) 0.0637(10) Uani 1 1 d . . . H22 H 0.1794 0.9605 0.6276 0.076 Uiso 1 1 calc R . . C23 C 0.2415(4) 0.9887(7) 0.56627(12) 0.0625(10) Uani 1 1 d . . . H23 H 0.2875 1.1269 0.5719 0.075 Uiso 1 1 calc R . . C24 C 0.2409(4) 0.8856(7) 0.52326(12) 0.0544(9) Uani 1 1 d . . . N1 N 0.2627(6) 0.3855(12) 0.25493(14) 0.1061(17) Uani 1 1 d . . . H1A H 0.2065 0.3237 0.2338 0.127 Uiso 1 1 calc R . . C29 C 0.2302(6) 0.5752(14) 0.27400(19) 0.0997(18) Uani 1 1 d . . . H29 H 0.1438 0.6423 0.2645 0.120 Uiso 1 1 calc R . . C30 C 0.3141(7) 0.6767(12) 0.3062(2) 0.1056(18) Uani 1 1 d . . . H30 H 0.2874 0.8130 0.3187 0.127 Uiso 1 1 calc R . . C31 C 0.4358(7) 0.5832(15) 0.32052(19) 0.107(2) Uani 1 1 d . . . H31 H 0.4950 0.6522 0.3435 0.128 Uiso 1 1 calc R . . C32 C 0.4742(7) 0.3913(16) 0.3023(2) 0.114(2) Uani 1 1 d . . . H32 H 0.5606 0.3242 0.3117 0.137 Uiso 1 1 calc R . . C33 C 0.3823(9) 0.2938(12) 0.2689(3) 0.115(2) Uani 1 1 d . . . H33 H 0.4071 0.1575 0.2560 0.138 Uiso 1 1 calc R . . N2 N 0.7472(4) 0.6360(9) 0.24331(12) 0.0842(12) Uani 1 1 d . . . H2 H 0.8044 0.6847 0.2656 0.101 Uiso 1 1 calc R . . C34 C 0.6321(5) 0.7471(10) 0.22965(16) 0.0854(14) Uani 1 1 d . . . H34 H 0.6136 0.8812 0.2445 0.103 Uiso 1 1 calc R . . C35 C 0.5375(6) 0.6768(12) 0.19467(16) 0.0950(17) Uani 1 1 d . . . H35 H 0.4565 0.7604 0.1858 0.114 Uiso 1 1 calc R . . C36 C 0.5653(6) 0.4815(13) 0.17329(17) 0.1019(19) Uani 1 1 d . . . H36 H 0.5026 0.4275 0.1495 0.122 Uiso 1 1 calc R . . C37 C 0.6838(6) 0.3663(12) 0.18660(17) 0.110(2) Uani 1 1 d . . . H37 H 0.7047 0.2331 0.1719 0.132 Uiso 1 1 calc R . . C38 C 0.7730(5) 0.4463(12) 0.22184(16) 0.0965(18) Uani 1 1 d . . . H38 H 0.8546 0.3651 0.2311 0.116 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 C1 0.065(2) 0.052(2) 0.067(2) 0.001(2) -0.0060(18) -0.0055(19) C2 0.060(2) 0.064(3) 0.071(2) -0.004(2) -0.0075(19) 0.001(2) O1 0.0788(18) 0.088(2) 0.0692(17) -0.0114(18) 0.0079(14) -0.0117(18) C11 0.090(3) 0.082(3) 0.086(3) 0.006(3) 0.014(2) -0.008(3) C3 0.079(3) 0.073(3) 0.085(3) -0.024(3) -0.003(2) -0.012(3) C4 0.072(3) 0.062(3) 0.096(3) -0.018(3) 0.003(2) -0.017(2) C5 0.051(2) 0.049(2) 0.078(2) -0.001(2) -0.0035(17) -0.0016(18) C6 0.053(2) 0.052(2) 0.091(3) 0.002(2) 0.0005(19) -0.0050(19) C7 0.057(2) 0.057(3) 0.078(3) 0.005(2) -0.0020(19) 0.005(2) C12 0.074(3) 0.066(3) 0.081(3) 0.008(2) 0.009(2) 0.002(2) C13 0.074(3) 0.184(8) 0.120(4) 0.052(5) 0.009(3) -0.009(4) C14 0.093(3) 0.070(3) 0.072(3) 0.002(3) 0.011(2) 0.002(3) O2 0.081(2) 0.108(3) 0.192(4) 0.057(3) -0.024(2) -0.010(2) O3 0.117(3) 0.157(5) 0.178(4) 0.090(4) 0.073(3) 0.043(3) C8 0.086(3) 0.061(3) 0.072(3) -0.008(2) 0.001(2) -0.006(2) C9 0.089(3) 0.050(2) 0.073(2) -0.007(2) 0.001(2) -0.018(2) C10 0.058(2) 0.043(2) 0.067(2) -0.0016(18) -0.0078(17) 0.0025(18) C15 0.059(2) 0.051(2) 0.070(2) 0.000(2) -0.0084(17) -0.009(2) C16 0.062(2) 0.070(3) 0.067(2) -0.003(2) -0.0037(18) -0.007(2) O4 0.090(2) 0.104(3) 0.0701(17) -0.009(2) 0.0112(15) -0.033(2) C25 0.085(3) 0.092(4) 0.096(3) 0.003(3) 0.017(3) -0.028(3) C17 0.068(2) 0.069(3) 0.071(2) -0.015(2) 0.0003(19) -0.009(2) C18 0.056(2) 0.052(2) 0.082(3) -0.014(2) -0.0091(19) -0.0076(19) C19 0.0482(18) 0.045(2) 0.064(2) 0.0004(19) -0.0088(16) 0.0054(18) C20 0.055(2) 0.045(2) 0.078(2) 0.006(2) -0.0104(18) -0.0033(18) C21 0.054(2) 0.049(2) 0.068(2) 0.009(2) -0.0072(17) 0.0020(19) C26 0.059(2) 0.070(3) 0.073(2) 0.009(2) -0.0001(18) 0.001(2) C27 0.090(3) 0.101(5) 0.140(5) 0.036(4) 0.043(3) 0.029(3) C28 0.062(2) 0.065(3) 0.073(2) 0.008(2) 0.0026(18) -0.005(2) O5 0.086(2) 0.115(3) 0.101(2) 0.046(2) 0.0074(17) -0.017(2) O6 0.082(2) 0.160(4) 0.134(3) 0.086(3) -0.024(2) -0.028(3) C22 0.070(2) 0.054(2) 0.063(2) -0.001(2) -0.0063(18) 0.005(2) C23 0.073(2) 0.041(2) 0.070(2) 0.001(2) -0.0084(19) -0.006(2) C24 0.054(2) 0.045(2) 0.061(2) 0.0006(18) -0.0074(16) 0.0031(18) N1 0.112(4) 0.133(5) 0.075(3) -0.028(3) 0.017(3) -0.037(4) C29 0.093(4) 0.118(5) 0.088(4) 0.009(4) 0.008(3) 0.021(4) C30 0.138(5) 0.077(4) 0.108(4) -0.017(4) 0.039(4) 0.003(4) C31 0.104(4) 0.133(6) 0.083(3) -0.017(4) 0.003(3) -0.027(5) C32 0.089(4) 0.138(7) 0.118(5) 0.030(5) 0.025(4) 0.033(4) C33 0.145(6) 0.071(3) 0.145(6) -0.014(4) 0.085(5) -0.001(4) N2 0.079(2) 0.099(3) 0.073(2) -0.029(2) 0.0022(18) 0.004(2) C34 0.098(3) 0.078(3) 0.083(3) -0.015(3) 0.025(3) 0.016(3) C35 0.093(3) 0.114(5) 0.079(3) 0.015(4) 0.014(3) 0.035(4) C36 0.099(4) 0.126(5) 0.076(3) -0.016(4) -0.011(3) 0.005(4) C37 0.138(5) 0.102(5) 0.086(3) -0.040(4) -0.006(3) 0.027(4) C38 0.092(3) 0.108(5) 0.086(3) -0.026(4) -0.003(3) 0.026(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 C1 C2 1.357(6) . ? C1 C10 1.424(5) . ? C1 H1 0.9300 . ? C2 O1 1.371(5) . ? C2 C3 1.410(7) . ? O1 C11 1.417(6) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C3 C4 1.359(6) . ? C3 H3 0.9300 . ? C4 C5 1.399(6) . ? C4 H4 0.9300 . ? C5 C10 1.411(6) . ? C5 C6 1.418(5) . ? C6 C7 1.363(6) . ? C6 H6 0.9300 . ? C7 C8 1.406(6) . ? C7 C12 1.522(6) . ? C12 C14 1.495(7) . ? C12 C13 1.513(7) . ? C12 H12 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O2 1.232(5) . ? C14 O3 1.240(6) . ? C8 C9 1.356(6) . ? C8 H8 0.9300 . ? C9 C10 1.407(5) . ? C9 H9 0.9300 . ? C15 C16 1.377(6) . ? C15 C24 1.411(5) . ? C15 H15 0.9300 . ? C16 O4 1.354(5) . ? C16 C17 1.406(7) . ? O4 C25 1.416(6) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C17 C18 1.356(6) . ? C17 H17 0.9300 . ? C18 C19 1.404(5) . ? C18 H18 0.9300 . ? C19 C24 1.411(5) . ? C19 C20 1.417(5) . ? C20 C21 1.374(5) . ? C20 H20 0.9300 . ? C21 C22 1.409(6) . ? C21 C26 1.512(5) . ? C26 C28 1.504(6) . ? C26 C27 1.524(7) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 O6 1.184(5) . ? C28 O5 1.296(5) . ? C22 C23 1.359(5) . ? C22 H22 0.9300 . ? C23 C24 1.414(5) . ? C23 H23 0.9300 . ? N1 C33 1.290(8) . ? N1 C29 1.304(9) . ? N1 H1A 0.8600 . ? C29 C30 1.322(8) . ? C29 H29 0.9300 . ? C30 C31 1.314(9) . ? C30 H30 0.9300 . ? C31 C32 1.321(11) . ? C31 H31 0.9300 . ? C32 C33 1.375(10) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? N2 C34 1.305(6) . ? N2 C38 1.322(7) . ? N2 H2 0.8600 . ? C34 C35 1.364(7) . ? C34 H34 0.9300 . ? C35 C36 1.352(9) . ? C35 H35 0.9300 . ? C36 C37 1.341(8) . ? C36 H36 0.9300 . ? C37 C38 1.359(7) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 120.5(4) . . ? C2 C1 H1 119.7 . . ? C10 C1 H1 119.7 . . ? C1 C2 O1 125.8(4) . . ? C1 C2 C3 119.3(4) . . ? O1 C2 C3 114.8(4) . . ? C2 O1 C11 117.2(4) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C4 C3 C2 121.3(4) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 120.7(4) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C10 118.7(4) . . ? C4 C5 C6 122.7(4) . . ? C10 C5 C6 118.5(4) . . ? C7 C6 C5 122.1(4) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C6 C7 C8 118.0(4) . . ? C6 C7 C12 122.7(4) . . ? C8 C7 C12 119.2(4) . . ? C14 C12 C13 112.6(5) . . ? C14 C12 C7 110.5(4) . . ? C13 C12 C7 113.2(4) . . ? C14 C12 H12 106.7 . . ? C13 C12 H12 106.7 . . ? C7 C12 H12 106.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 O3 118.9(5) . . ? O2 C14 C12 123.9(5) . . ? O3 C14 C12 117.2(4) . . ? C9 C8 C7 121.8(4) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C10 120.8(4) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C5 118.6(4) . . ? C9 C10 C1 122.0(4) . . ? C5 C10 C1 119.4(4) . . ? C16 C15 C24 120.5(4) . . ? C16 C15 H15 119.8 . . ? C24 C15 H15 119.8 . . ? O4 C16 C15 126.1(4) . . ? O4 C16 C17 114.6(4) . . ? C15 C16 C17 119.3(4) . . ? C16 O4 C25 117.7(4) . . ? O4 C25 H25A 109.5 . . ? O4 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O4 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C18 C17 C16 121.2(4) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 120.7(4) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C24 118.9(4) . . ? C18 C19 C20 121.9(4) . . ? C24 C19 C20 119.1(3) . . ? C21 C20 C19 122.2(4) . . ? C21 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C20 C21 C22 117.5(4) . . ? C20 C21 C26 120.2(4) . . ? C22 C21 C26 122.2(4) . . ? C28 C26 C21 112.7(3) . . ? C28 C26 C27 109.9(4) . . ? C21 C26 C27 113.4(4) . . ? C28 C26 H26 106.8 . . ? C21 C26 H26 106.8 . . ? C27 C26 H26 106.8 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O6 C28 O5 121.9(4) . . ? O6 C28 C26 125.1(4) . . ? O5 C28 C26 113.0(4) . . ? C23 C22 C21 122.0(4) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C22 C23 C24 121.1(4) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.5 . . ? C15 C24 C19 119.4(3) . . ? C15 C24 C23 122.6(4) . . ? C19 C24 C23 118.0(4) . . ? C33 N1 C29 117.5(6) . . ? C33 N1 H1A 121.2 . . ? C29 N1 H1A 121.2 . . ? N1 C29 C30 123.1(6) . . ? N1 C29 H29 118.5 . . ? C30 C29 H29 118.5 . . ? C31 C30 C29 119.4(6) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C30 C31 C32 120.1(6) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? C31 C32 C33 117.9(6) . . ? C31 C32 H32 121.1 . . ? C33 C32 H32 121.1 . . ? N1 C33 C32 122.1(6) . . ? N1 C33 H33 119.0 . . ? C32 C33 H33 119.0 . . ? C34 N2 C38 117.9(4) . . ? C34 N2 H2 121.0 . . ? C38 N2 H2 121.0 . . ? N2 C34 C35 123.4(5) . . ? N2 C34 H34 118.3 . . ? C35 C34 H34 118.3 . . ? C36 C35 C34 117.8(5) . . ? C36 C35 H35 121.1 . . ? C34 C35 H35 121.1 . . ? C37 C36 C35 119.6(5) . . ? C37 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? C36 C37 C38 119.4(6) . . ? C36 C37 H37 120.3 . . ? C38 C37 H37 120.3 . . ? N2 C38 C37 121.9(5) . . ? N2 C38 H38 119.0 . . ? C37 C38 H38 119.0 . . ? 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 C10 C1 C2 O1 177.8(4) . . . . ? C10 C1 C2 C3 -2.2(6) . . . . ? C1 C2 O1 C11 -2.7(6) . . . . ? C3 C2 O1 C11 177.3(4) . . . . ? C1 C2 C3 C4 2.1(7) . . . . ? O1 C2 C3 C4 -177.9(4) . . . . ? C2 C3 C4 C5 0.2(7) . . . . ? C3 C4 C5 C10 -2.3(6) . . . . ? C3 C4 C5 C6 176.1(4) . . . . ? C4 C5 C6 C7 -177.4(4) . . . . ? C10 C5 C6 C7 0.9(6) . . . . ? C5 C6 C7 C8 -2.4(6) . . . . ? C5 C6 C7 C12 177.3(4) . . . . ? C6 C7 C12 C14 -79.5(5) . . . . ? C8 C7 C12 C14 100.1(5) . . . . ? C6 C7 C12 C13 47.7(7) . . . . ? C8 C7 C12 C13 -132.7(6) . . . . ? C13 C12 C14 O2 -152.9(6) . . . . ? C7 C12 C14 O2 -25.3(7) . . . . ? C13 C12 C14 O3 29.0(7) . . . . ? C7 C12 C14 O3 156.6(5) . . . . ? C6 C7 C8 C9 1.6(6) . . . . ? C12 C7 C8 C9 -178.1(4) . . . . ? C7 C8 C9 C10 0.7(7) . . . . ? C8 C9 C10 C5 -2.2(6) . . . . ? C8 C9 C10 C1 175.4(4) . . . . ? C4 C5 C10 C9 179.8(4) . . . . ? C6 C5 C10 C9 1.4(5) . . . . ? C4 C5 C10 C1 2.1(5) . . . . ? C6 C5 C10 C1 -176.3(3) . . . . ? C2 C1 C10 C9 -177.5(4) . . . . ? C2 C1 C10 C5 0.1(5) . . . . ? C24 C15 C16 O4 -178.5(4) . . . . ? C24 C15 C16 C17 1.7(6) . . . . ? C15 C16 O4 C25 11.1(7) . . . . ? C17 C16 O4 C25 -169.1(4) . . . . ? O4 C16 C17 C18 178.5(4) . . . . ? C15 C16 C17 C18 -1.7(6) . . . . ? C16 C17 C18 C19 0.0(6) . . . . ? C17 C18 C19 C24 1.7(5) . . . . ? C17 C18 C19 C20 -176.1(4) . . . . ? C18 C19 C20 C21 178.3(3) . . . . ? C24 C19 C20 C21 0.5(5) . . . . ? C19 C20 C21 C22 0.8(5) . . . . ? C19 C20 C21 C26 -178.4(3) . . . . ? C20 C21 C26 C28 106.4(4) . . . . ? C22 C21 C26 C28 -72.8(5) . . . . ? C20 C21 C26 C27 -128.0(4) . . . . ? C22 C21 C26 C27 52.9(5) . . . . ? C21 C26 C28 O6 16.1(7) . . . . ? C27 C26 C28 O6 -111.4(6) . . . . ? C21 C26 C28 O5 -161.4(4) . . . . ? C27 C26 C28 O5 71.0(6) . . . . ? C20 C21 C22 C23 -0.7(5) . . . . ? C26 C21 C22 C23 178.5(4) . . . . ? C21 C22 C23 C24 -0.8(6) . . . . ? C16 C15 C24 C19 0.1(5) . . . . ? C16 C15 C24 C23 178.0(4) . . . . ? C18 C19 C24 C15 -1.7(5) . . . . ? C20 C19 C24 C15 176.2(3) . . . . ? C18 C19 C24 C23 -179.8(3) . . . . ? C20 C19 C24 C23 -1.8(5) . . . . ? C22 C23 C24 C15 -175.9(3) . . . . ? C22 C23 C24 C19 2.0(5) . . . . ? C33 N1 C29 C30 0.7(9) . . . . ? N1 C29 C30 C31 -0.8(10) . . . . ? C29 C30 C31 C32 1.0(10) . . . . ? C30 C31 C32 C33 -1.0(10) . . . . ? C29 N1 C33 C32 -0.7(9) . . . . ? C31 C32 C33 N1 0.9(10) . . . . ? C38 N2 C34 C35 0.4(8) . . . . ? N2 C34 C35 C36 0.1(9) . . . . ? C34 C35 C36 C37 -0.7(9) . . . . ? C35 C36 C37 C38 1.0(10) . . . . ? C34 N2 C38 C37 -0.1(8) . . . . ? C36 C37 C38 N2 -0.5(10) . . . . ? 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 N2 H2 O5 0.86 1.77 2.631(5) 174.3 2_656 N1 H1A O3 0.86 1.91 2.747(6) 165.1 2_646 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.439 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.037