# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Marta Iglesias' _publ_contact_author_email marta.iglesias@icmm.csic.es loop_ _publ_author_name 'Marta Iglesias' 'Gonzalo Villaverde' 'Avelina Arnanz' 'Natalia Snejko' 'M. Angeles Monge' 'Felix Sanchez' data_RR-6 _database_code_depnum_ccdc_archive 'CCDC 805292' #TrackingRef '3534_web_deposit_cif_file_0_MartaIglesias_1292844350.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H27 N3 O' _chemical_formula_sum 'C28 H27 N3 O' _chemical_formula_weight 421.53 _chemical_absolute_configuration syn 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 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 10.414(3) _cell_length_b 13.565(3) _cell_length_c 15.401(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2175.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7122 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 24.89 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 15489 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.40 _reflns_number_total 2280 _reflns_number_gt 2030 _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^)+(0.0341P)^2^+0.1860P] 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 SHELXL _refine_ls_extinction_coef 0.0112(15) _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 10(10) _refine_ls_number_reflns 2280 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_restrained_S_all 1.148 _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 N3 N 1.17337(17) 0.38568(13) 0.67868(12) 0.0429(5) Uani 1 1 d . . . C2 C 0.7032(2) 0.47817(16) 0.84683(14) 0.0399(5) Uani 1 1 d . . . N2 N 0.86067(18) 0.36521(13) 0.78756(12) 0.0455(5) Uani 1 1 d . . . N4 N 0.72105(19) 0.31289(14) 0.90069(13) 0.0492(5) Uani 1 1 d . . . C5 C 0.6467(2) 0.57374(16) 0.85104(15) 0.0456(5) Uani 1 1 d . . . C6 C 0.8023(2) 0.45832(16) 0.78488(14) 0.0426(5) Uani 1 1 d . . . C7 C 1.2946(2) 0.42008(16) 0.68999(15) 0.0422(5) Uani 1 1 d . . . C8 C 1.0880(2) 0.38950(17) 0.74416(15) 0.0446(5) Uani 1 1 d . . . C9 C 0.6698(2) 0.40595(16) 0.91022(14) 0.0421(5) Uani 1 1 d . . . C10 C 0.7781(2) 0.28367(16) 0.81781(15) 0.0458(6) Uani 1 1 d . . . C11 C 0.5335(2) 0.52557(19) 0.98041(18) 0.0568(6) Uani 1 1 d . . . H11 H 0.4781 0.5411 1.0258 0.068 Uiso 1 1 calc R . . C12 C 1.3477(2) 0.36202(17) 0.53869(16) 0.0499(6) Uani 1 1 d . . . C13 C 0.6865(3) 0.64557(17) 0.79085(17) 0.0554(6) Uani 1 1 d . . . H13 H 0.6472 0.7071 0.7904 0.066 Uiso 1 1 calc R . . C14 C 0.9593(2) 0.34318(18) 0.72310(15) 0.0502(6) Uani 1 1 d . . . H14A H 0.9308 0.3668 0.6668 0.060 Uiso 1 1 calc R . . H14B H 0.9697 0.2723 0.7191 0.060 Uiso 1 1 calc R . . C15 C 0.7440(2) 0.24308(18) 0.97137(17) 0.0551(6) Uani 1 1 d . . . H15 H 0.6640 0.2315 1.0033 0.066 Uiso 1 1 calc R . . C16 C 1.3827(2) 0.41062(16) 0.61551(15) 0.0437(5) Uani 1 1 d . . . C17 C 1.4348(3) 0.3520(2) 0.47062(18) 0.0649(7) Uani 1 1 d . . . H17 H 1.4101 0.3197 0.4200 0.078 Uiso 1 1 calc R . . C18 C 0.5893(2) 0.43177(18) 0.97765(16) 0.0514(6) Uani 1 1 d . . . H18 H 0.5720 0.3866 1.0215 0.062 Uiso 1 1 calc R . . C19 C 1.2411(2) 0.4668(2) 0.83582(17) 0.0588(7) Uani 1 1 d . . . H19 H 1.2637 0.4949 0.8887 0.071 Uiso 1 1 calc R . . C20 C 0.8548(2) 0.19110(17) 0.84273(17) 0.0563(6) Uani 1 1 d . . . H20A H 0.8559 0.1438 0.7955 0.068 Uiso 1 1 calc R . . H20B H 0.9424 0.2078 0.8582 0.068 Uiso 1 1 calc R . . C21 C 1.5567(3) 0.3894(2) 0.4777(2) 0.0725(8) Uani 1 1 d . . . H21 H 1.6146 0.3814 0.4323 0.087 Uiso 1 1 calc R . . C22 C 1.1177(2) 0.43008(19) 0.82368(15) 0.0540(6) Uani 1 1 d . . . H22 H 1.0570 0.4329 0.8679 0.065 Uiso 1 1 calc R . . C23 C 0.5581(2) 0.59443(18) 0.91872(17) 0.0547(6) Uani 1 1 d . . . H23 H 0.5169 0.6552 0.9208 0.066 Uiso 1 1 calc R . . C24 C 1.3296(2) 0.46157(18) 0.77001(16) 0.0541(6) Uani 1 1 d . . . H24 H 1.4124 0.4854 0.7784 0.065 Uiso 1 1 calc R . . C25 C 1.5937(3) 0.4387(2) 0.5517(2) 0.0755(9) Uani 1 1 d . . . H25 H 1.6762 0.4646 0.5560 0.091 Uiso 1 1 calc R . . C26 C 0.7823(3) 0.62549(19) 0.73331(17) 0.0598(7) Uani 1 1 d . . . H26 H 0.8092 0.6747 0.6954 0.072 Uiso 1 1 calc R . . C27 C 1.5082(2) 0.4496(2) 0.61912(19) 0.0623(7) Uani 1 1 d . . . H27 H 1.5339 0.4836 0.6686 0.075 Uiso 1 1 calc R . . C28 C 0.8414(2) 0.53250(18) 0.72969(16) 0.0533(6) Uani 1 1 d . . . H28 H 0.9071 0.5210 0.6900 0.064 Uiso 1 1 calc R . . C29 C 0.7813(3) 0.15050(18) 0.92129(19) 0.0616(7) Uani 1 1 d . . . H29A H 0.7059 0.1140 0.9031 0.074 Uiso 1 1 calc R . . H29B H 0.8355 0.1079 0.9561 0.074 Uiso 1 1 calc R . . C30 C 0.6730(3) 0.25982(19) 0.75074(18) 0.0621(7) Uani 1 1 d . . . H30A H 0.6158 0.3150 0.7456 0.093 Uiso 1 1 calc R . . H30B H 0.6257 0.2029 0.7694 0.093 Uiso 1 1 calc R . . H30C H 0.7120 0.2468 0.6955 0.093 Uiso 1 1 calc R . . C31 C 0.8477(3) 0.2783(2) 1.03359(19) 0.0743(8) Uani 1 1 d . . . H31A H 0.9272 0.2856 1.0028 0.112 Uiso 1 1 calc R . . H31B H 0.8583 0.2309 1.0793 0.112 Uiso 1 1 calc R . . H31C H 0.8230 0.3406 1.0580 0.112 Uiso 1 1 calc R . . O2 O 1.22959(16) 0.32212(16) 0.52571(12) 0.0688(5) Uani 1 1 d . . . H2 H 1.1863 0.3286 0.5698 0.103 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 N3 0.0370(10) 0.0436(10) 0.0481(11) -0.0011(8) 0.0019(8) 0.0021(9) C2 0.0319(11) 0.0414(11) 0.0464(12) -0.0046(10) -0.0041(10) -0.0035(9) N2 0.0385(10) 0.0463(11) 0.0518(11) -0.0044(9) 0.0092(9) -0.0012(9) N4 0.0489(11) 0.0430(10) 0.0557(12) 0.0033(9) 0.0106(10) 0.0066(9) C5 0.0369(11) 0.0409(12) 0.0589(14) -0.0050(11) -0.0113(11) -0.0024(10) C6 0.0376(12) 0.0464(12) 0.0437(12) -0.0015(10) -0.0029(10) -0.0066(10) C7 0.0378(12) 0.0380(11) 0.0509(13) 0.0052(10) -0.0021(10) 0.0030(10) C8 0.0395(12) 0.0482(13) 0.0462(13) -0.0027(10) 0.0040(10) 0.0027(10) C9 0.0333(11) 0.0430(12) 0.0499(13) -0.0033(11) 0.0007(10) -0.0021(10) C10 0.0395(12) 0.0425(13) 0.0555(14) -0.0061(11) 0.0041(11) -0.0002(10) C11 0.0444(13) 0.0580(15) 0.0680(17) -0.0198(14) 0.0080(13) 0.0025(12) C12 0.0432(13) 0.0513(14) 0.0550(14) 0.0078(11) 0.0060(11) 0.0069(12) C13 0.0539(15) 0.0410(12) 0.0713(17) 0.0022(12) -0.0155(14) -0.0005(12) C14 0.0413(12) 0.0572(14) 0.0520(14) -0.0108(12) 0.0080(11) -0.0024(11) C15 0.0503(15) 0.0483(14) 0.0666(16) 0.0119(13) 0.0127(12) 0.0033(12) C16 0.0389(12) 0.0401(12) 0.0521(14) 0.0095(10) 0.0014(11) 0.0036(10) C17 0.0669(18) 0.0700(17) 0.0577(15) 0.0020(14) 0.0188(14) 0.0088(15) C18 0.0439(13) 0.0550(15) 0.0552(14) -0.0019(12) 0.0082(11) -0.0004(12) C19 0.0559(15) 0.0724(17) 0.0481(14) -0.0109(13) -0.0073(13) -0.0009(14) C20 0.0494(13) 0.0476(13) 0.0718(16) -0.0079(12) 0.0022(13) 0.0060(13) C21 0.0623(18) 0.0753(19) 0.080(2) 0.0168(17) 0.0320(16) 0.0069(16) C22 0.0475(13) 0.0691(16) 0.0455(14) -0.0066(12) 0.0039(11) 0.0000(13) C23 0.0464(13) 0.0431(13) 0.0745(17) -0.0144(13) -0.0064(13) 0.0045(12) C24 0.0420(13) 0.0609(15) 0.0596(15) -0.0038(13) -0.0080(12) -0.0031(12) C25 0.0491(16) 0.080(2) 0.097(2) 0.0188(18) 0.0182(16) -0.0089(15) C26 0.0606(16) 0.0570(15) 0.0619(16) 0.0146(13) -0.0098(14) -0.0144(14) C27 0.0483(14) 0.0645(17) 0.0742(18) 0.0062(14) 0.0053(13) -0.0080(13) C28 0.0486(14) 0.0579(15) 0.0532(14) 0.0054(12) 0.0012(12) -0.0074(13) C29 0.0547(14) 0.0452(14) 0.0850(19) 0.0070(13) -0.0003(15) 0.0018(13) C30 0.0539(16) 0.0569(15) 0.0756(17) -0.0096(13) -0.0082(13) -0.0039(13) C31 0.0788(19) 0.0760(19) 0.0682(17) -0.0045(15) -0.0059(16) 0.0157(17) O2 0.0526(11) 0.0973(14) 0.0564(10) -0.0179(11) 0.0065(9) -0.0108(11) _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 N3 C8 1.345(3) . ? N3 C7 1.357(3) . ? C2 C5 1.425(3) . ? C2 C9 1.426(3) . ? C2 C6 1.431(3) . ? N2 C6 1.403(3) . ? N2 C14 1.459(3) . ? N2 C10 1.477(3) . ? N4 C9 1.378(3) . ? N4 C10 1.462(3) . ? N4 C15 1.462(3) . ? C5 C13 1.407(3) . ? C5 C23 1.420(3) . ? C6 C28 1.379(3) . ? C7 C24 1.403(3) . ? C7 C16 1.475(3) . ? C8 C22 1.378(3) . ? C8 C14 1.516(3) . ? C9 C18 1.380(3) . ? C10 C20 1.537(3) . ? C10 C30 1.539(3) . ? C11 C23 1.357(4) . ? C11 C18 1.399(3) . ? C12 O2 1.359(3) . ? C12 C17 1.393(3) . ? C12 C16 1.403(3) . ? C13 C26 1.361(4) . ? C15 C31 1.521(4) . ? C15 C29 1.524(4) . ? C16 C27 1.410(3) . ? C17 C21 1.372(4) . ? C19 C24 1.371(3) . ? C19 C22 1.391(3) . ? C20 C29 1.534(4) . ? C21 C25 1.376(4) . ? C25 C27 1.376(4) . ? C26 C28 1.405(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N3 C7 120.34(19) . . ? C5 C2 C9 119.6(2) . . ? C5 C2 C6 119.9(2) . . ? C9 C2 C6 120.20(19) . . ? C6 N2 C14 118.00(19) . . ? C6 N2 C10 115.54(17) . . ? C14 N2 C10 118.12(17) . . ? C9 N4 C10 119.90(19) . . ? C9 N4 C15 125.25(19) . . ? C10 N4 C15 114.06(18) . . ? C13 C5 C23 122.5(2) . . ? C13 C5 C2 118.6(2) . . ? C23 C5 C2 118.8(2) . . ? C28 C6 N2 123.2(2) . . ? C28 C6 C2 119.1(2) . . ? N2 C6 C2 117.55(19) . . ? N3 C7 C24 119.5(2) . . ? N3 C7 C16 116.69(19) . . ? C24 C7 C16 123.8(2) . . ? N3 C8 C22 122.2(2) . . ? N3 C8 C14 114.08(19) . . ? C22 C8 C14 123.7(2) . . ? N4 C9 C18 123.2(2) . . ? N4 C9 C2 117.50(19) . . ? C18 C9 C2 119.3(2) . . ? N4 C10 N2 107.99(17) . . ? N4 C10 C20 102.38(19) . . ? N2 C10 C20 112.82(18) . . ? N4 C10 C30 110.7(2) . . ? N2 C10 C30 111.10(19) . . ? C20 C10 C30 111.44(19) . . ? C23 C11 C18 121.8(2) . . ? O2 C12 C17 116.1(2) . . ? O2 C12 C16 123.2(2) . . ? C17 C12 C16 120.8(2) . . ? C26 C13 C5 120.4(2) . . ? N2 C14 C8 113.08(18) . . ? N4 C15 C31 112.4(2) . . ? N4 C15 C29 101.5(2) . . ? C31 C15 C29 113.4(2) . . ? C12 C16 C27 116.8(2) . . ? C12 C16 C7 122.3(2) . . ? C27 C16 C7 120.9(2) . . ? C21 C17 C12 120.4(3) . . ? C9 C18 C11 120.4(2) . . ? C24 C19 C22 120.2(2) . . ? C29 C20 C10 103.36(19) . . ? C17 C21 C25 120.3(3) . . ? C8 C22 C19 118.0(2) . . ? C11 C23 C5 120.0(2) . . ? C19 C24 C7 119.7(2) . . ? C21 C25 C27 119.7(3) . . ? C13 C26 C28 121.8(2) . . ? C25 C27 C16 122.0(3) . . ? C6 C28 C26 120.1(2) . . ? C15 C29 C20 103.3(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.111 _refine_diff_density_min -0.100 _refine_diff_density_rms 0.025 # Attachment '3535_web_deposit_cif_file_1_MartaIglesias_1292844350.cif' data_RR-8 _database_code_depnum_ccdc_archive 'CCDC 805293' #TrackingRef '3535_web_deposit_cif_file_1_MartaIglesias_1292844350.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H34 N2 O' _chemical_formula_sum 'C28 H34 N2 O' _chemical_formula_weight 414.57 _chemical_absolute_configuration syn 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 9.8047(8) _cell_length_b 8.8134(8) _cell_length_c 14.0070(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.3630(10) _cell_angle_gamma 90.00 _cell_volume 1210.04(18) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2378 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 20.98 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 1.180 _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 466 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 8037 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.39 _reflns_number_total 4000 _reflns_number_gt 2598 _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^)+(0.0510P)^2^+0.0244P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 4000 _refine_ls_number_parameters 287 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1082 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.002 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 0.2562(2) 0.6243(3) 0.28552(15) 0.0668(7) Uani 1 1 d . . . H1 H 0.2513 0.6011 0.2288 0.100 Uiso 1 1 calc R . . N2 N 0.3375(3) 0.5579(3) 0.11592(17) 0.0541(7) Uani 1 1 d . . . C3 C 0.3888(3) 0.6428(4) 0.3124(2) 0.0500(8) Uani 1 1 d . . . C4 C 0.4203(3) 0.6872(4) 0.4068(2) 0.0475(8) Uani 1 1 d . . . C5 C 0.1340(3) 0.3257(4) 0.0441(2) 0.0527(9) Uani 1 1 d . . . N1 N 0.1713(3) 0.3098(3) 0.14179(17) 0.0530(7) Uani 1 1 d . . . C7 C 0.6648(3) 0.6758(3) 0.3670(2) 0.0487(8) Uani 1 1 d . . . C8 C 0.4922(3) 0.6162(4) 0.2464(2) 0.0497(9) Uani 1 1 d . . . C9 C 0.5585(3) 0.7019(4) 0.4295(2) 0.0502(8) Uani 1 1 d . . . H9 H 0.5821 0.7317 0.4914 0.060 Uiso 1 1 calc R . . C10 C 0.3114(3) 0.5331(4) 0.0171(2) 0.0516(9) Uani 1 1 d . . . C11 C 0.1788(3) 0.4272(4) -0.1164(2) 0.0558(9) Uani 1 1 d . . . C12 C 0.6287(3) 0.6342(4) 0.2748(2) 0.0522(9) Uani 1 1 d . . . H12 H 0.6966 0.6177 0.2308 0.063 Uiso 1 1 calc R . . C13 C 0.2102(3) 0.4264(4) -0.0156(2) 0.0513(9) Uani 1 1 d . . . C14 C 0.3467(4) 0.6189(5) -0.1446(3) 0.0815(13) Uani 1 1 d . . . H14 H 0.3932 0.6809 -0.1865 0.098 Uiso 1 1 calc R . . C15 C 0.3095(3) 0.7181(4) 0.4790(2) 0.0529(9) Uani 1 1 d . . . C16 C 0.0257(4) 0.2482(5) 0.0053(3) 0.0735(12) Uani 1 1 d . . . H16 H -0.0276 0.1888 0.0447 0.088 Uiso 1 1 calc R . . C17 C 0.8120(3) 0.6935(4) 0.3987(2) 0.0629(10) Uani 1 1 d . . . H17A H 0.8412 0.7957 0.3871 0.094 Uiso 1 1 calc R . . H17B H 0.8675 0.6245 0.3635 0.094 Uiso 1 1 calc R . . H17C H 0.8212 0.6715 0.4657 0.094 Uiso 1 1 calc R . . C18 C 0.4595(3) 0.5740(4) 0.1486(2) 0.0548(9) Uani 1 1 d . . . H18 H 0.5310 0.5577 0.1074 0.066 Uiso 1 1 calc R . . C19 C 0.3753(4) 0.6265(5) -0.0462(3) 0.0732(11) Uani 1 1 d . . . H19 H 0.4392 0.6963 -0.0233 0.088 Uiso 1 1 calc R . . C20 C 0.0666(3) 0.2612(4) 0.2093(2) 0.0601(10) Uani 1 1 d . . . H20 H 0.0232 0.1676 0.1861 0.072 Uiso 1 1 calc R . . C21 C 0.2924(4) 0.2125(5) 0.1619(3) 0.0702(11) Uani 1 1 d . . . H21 H 0.3737 0.2635 0.1383 0.084 Uiso 1 1 calc R . . C22 C 0.3702(4) 0.7629(5) 0.5774(2) 0.0767(12) Uani 1 1 d . . . H22A H 0.2976 0.7843 0.6201 0.115 Uiso 1 1 calc R . . H22B H 0.4262 0.8514 0.5709 0.115 Uiso 1 1 calc R . . H22C H 0.4245 0.6808 0.6024 0.115 Uiso 1 1 calc R . . C23 C 0.2505(4) 0.5206(5) -0.1781(2) 0.0703(11) Uani 1 1 d . . . H23 H 0.2320 0.5153 -0.2434 0.084 Uiso 1 1 calc R . . C24 C -0.0072(4) 0.2560(5) -0.0925(3) 0.0773(12) Uani 1 1 d . . . H24 H -0.0831 0.2041 -0.1165 0.093 Uiso 1 1 calc R . . C25 C 0.0695(4) 0.3372(5) -0.1517(2) 0.0702(11) Uani 1 1 d . . . H25 H 0.0506 0.3343 -0.2171 0.084 Uiso 1 1 calc R . . C26 C 0.2175(4) 0.8490(4) 0.4440(3) 0.0799(12) Uani 1 1 d . . . H26A H 0.2705 0.9404 0.4402 0.120 Uiso 1 1 calc R . . H26B H 0.1451 0.8636 0.4880 0.120 Uiso 1 1 calc R . . H26C H 0.1796 0.8249 0.3820 0.120 Uiso 1 1 calc R . . C6 C 0.2986(4) 0.2128(6) 0.2696(3) 0.0982(14) Uani 1 1 d . . . H6A H 0.3527 0.2975 0.2933 0.118 Uiso 1 1 calc R . . H6B H 0.3385 0.1192 0.2937 0.118 Uiso 1 1 calc R . . C27 C 0.1518(4) 0.2276(5) 0.2998(3) 0.0880(13) Uani 1 1 d . . . H27A H 0.1431 0.3094 0.3456 0.106 Uiso 1 1 calc R . . H27B H 0.1215 0.1341 0.3291 0.106 Uiso 1 1 calc R . . C28 C -0.0408(4) 0.3831(5) 0.2214(3) 0.0868(13) Uani 1 1 d . . . H28A H -0.0877 0.4003 0.1614 0.130 Uiso 1 1 calc R . . H28B H 0.0022 0.4754 0.2425 0.130 Uiso 1 1 calc R . . H28C H -0.1050 0.3507 0.2679 0.130 Uiso 1 1 calc R . . C29 C 0.2220(4) 0.5766(5) 0.4931(3) 0.0762(12) Uani 1 1 d . . . H29A H 0.1513 0.5987 0.5373 0.114 Uiso 1 1 calc R . . H29B H 0.2781 0.4957 0.5179 0.114 Uiso 1 1 calc R . . H29C H 0.1816 0.5464 0.4329 0.114 Uiso 1 1 calc R . . C30 C 0.2829(4) 0.0554(5) 0.1178(4) 0.1043(15) Uani 1 1 d . . . H30A H 0.2711 0.0644 0.0498 0.156 Uiso 1 1 calc R . . H30B H 0.2064 0.0024 0.1434 0.156 Uiso 1 1 calc R . . H30C H 0.3651 0.0001 0.1324 0.156 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 0.0516(15) 0.098(2) 0.0508(14) -0.0090(14) 0.0009(11) -0.0050(14) N2 0.0464(16) 0.070(2) 0.0463(17) -0.0009(15) -0.0001(13) -0.0095(15) C3 0.0441(19) 0.060(2) 0.046(2) 0.0076(17) 0.0004(16) -0.0046(17) C4 0.051(2) 0.049(2) 0.0422(19) 0.0022(16) 0.0007(15) -0.0049(17) C5 0.045(2) 0.063(2) 0.050(2) -0.0120(19) 0.0001(17) 0.0008(18) N1 0.0479(17) 0.0685(18) 0.0428(16) 0.0031(14) 0.0026(13) -0.0027(15) C7 0.053(2) 0.050(2) 0.043(2) -0.0039(16) -0.0009(16) -0.0069(16) C8 0.047(2) 0.059(2) 0.044(2) 0.0007(16) 0.0031(16) -0.0037(17) C9 0.065(2) 0.046(2) 0.0393(18) -0.0018(16) -0.0043(17) -0.0026(18) C10 0.046(2) 0.072(3) 0.036(2) -0.0031(18) 0.0000(16) 0.000(2) C11 0.054(2) 0.075(3) 0.038(2) -0.0135(19) 0.0039(17) 0.004(2) C12 0.051(2) 0.057(2) 0.050(2) 0.0055(17) 0.0041(16) -0.0016(17) C13 0.0395(19) 0.066(2) 0.049(2) -0.0091(18) 0.0075(15) 0.0060(18) C14 0.064(2) 0.128(4) 0.053(2) 0.012(2) -0.0012(19) -0.017(3) C15 0.055(2) 0.058(2) 0.0455(19) 0.0018(17) 0.0090(16) -0.0003(19) C16 0.075(3) 0.084(3) 0.062(3) -0.001(2) -0.005(2) -0.023(2) C17 0.052(2) 0.073(3) 0.063(2) -0.001(2) -0.0051(16) -0.0063(19) C18 0.050(2) 0.070(2) 0.045(2) -0.0005(18) 0.0071(16) -0.0061(18) C19 0.061(2) 0.105(3) 0.053(2) 0.011(2) -0.0041(18) -0.023(2) C20 0.068(2) 0.059(2) 0.053(2) 0.0000(18) 0.0097(19) -0.009(2) C21 0.054(2) 0.068(3) 0.088(3) 0.007(2) -0.0084(19) 0.007(2) C22 0.084(3) 0.100(3) 0.046(2) -0.011(2) 0.0094(19) 0.001(2) C23 0.060(2) 0.109(3) 0.042(2) -0.004(2) 0.0045(19) -0.003(2) C24 0.072(3) 0.095(3) 0.065(3) -0.019(2) -0.008(2) -0.022(2) C25 0.069(3) 0.093(3) 0.048(2) -0.021(2) -0.007(2) 0.002(2) C26 0.086(3) 0.077(3) 0.077(3) 0.003(2) 0.014(2) 0.027(2) C6 0.099(4) 0.107(4) 0.087(3) 0.026(3) -0.026(3) -0.007(3) C27 0.112(4) 0.087(3) 0.065(3) 0.016(2) -0.005(2) -0.016(3) C28 0.080(3) 0.090(3) 0.092(3) -0.009(3) 0.035(2) -0.002(3) C29 0.080(3) 0.082(3) 0.068(2) -0.005(2) 0.024(2) -0.006(2) C30 0.078(3) 0.071(3) 0.164(5) -0.007(3) 0.004(3) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.355(3) . ? O1 H1 0.8200 . ? N2 C18 1.279(3) . ? N2 C10 1.419(4) . ? C3 C4 1.407(4) . ? C3 C8 1.407(4) . ? C4 C9 1.390(4) . ? C4 C15 1.526(4) . ? C5 C16 1.364(4) . ? C5 N1 1.415(4) . ? C5 C13 1.441(4) . ? N1 C20 1.475(4) . ? N1 C21 1.486(4) . ? C7 C12 1.380(4) . ? C7 C9 1.395(4) . ? C7 C17 1.509(4) . ? C8 C12 1.397(4) . ? C8 C18 1.448(4) . ? C9 H9 0.9300 . ? C10 C19 1.373(5) . ? C10 C13 1.434(4) . ? C11 C23 1.396(5) . ? C11 C25 1.413(5) . ? C11 C13 1.437(4) . ? C12 H12 0.9300 . ? C14 C23 1.356(5) . ? C14 C19 1.401(5) . ? C14 H14 0.9300 . ? C15 C29 1.529(5) . ? C15 C26 1.538(5) . ? C15 C22 1.539(4) . ? C16 C24 1.401(5) . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C28 1.517(5) . ? C20 C27 1.531(5) . ? C20 H20 0.9800 . ? C21 C6 1.507(5) . ? C21 C30 1.518(6) . ? C21 H21 0.9800 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23 0.9300 . ? C24 C25 1.341(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C6 C27 1.515(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? 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 H1 109.5 . . ? C18 N2 C10 120.8(3) . . ? O1 C3 C4 118.8(3) . . ? O1 C3 C8 119.9(3) . . ? C4 C3 C8 121.3(3) . . ? C9 C4 C3 115.5(3) . . ? C9 C4 C15 122.5(3) . . ? C3 C4 C15 121.9(3) . . ? C16 C5 N1 121.1(3) . . ? C16 C5 C13 119.1(3) . . ? N1 C5 C13 119.8(3) . . ? C5 N1 C20 118.7(3) . . ? C5 N1 C21 115.3(3) . . ? C20 N1 C21 106.0(3) . . ? C12 C7 C9 116.8(3) . . ? C12 C7 C17 121.6(3) . . ? C9 C7 C17 121.5(3) . . ? C12 C8 C3 119.6(3) . . ? C12 C8 C18 119.2(3) . . ? C3 C8 C18 121.2(3) . . ? C4 C9 C7 125.4(3) . . ? C4 C9 H9 117.3 . . ? C7 C9 H9 117.3 . . ? C19 C10 N2 117.6(3) . . ? C19 C10 C13 120.6(3) . . ? N2 C10 C13 121.4(3) . . ? C23 C11 C25 120.2(3) . . ? C23 C11 C13 120.8(3) . . ? C25 C11 C13 119.0(3) . . ? C7 C12 C8 121.3(3) . . ? C7 C12 H12 119.3 . . ? C8 C12 H12 119.3 . . ? C10 C13 C11 116.2(3) . . ? C10 C13 C5 125.7(3) . . ? C11 C13 C5 118.1(3) . . ? C23 C14 C19 119.5(4) . . ? C23 C14 H14 120.3 . . ? C19 C14 H14 120.3 . . ? C4 C15 C29 110.5(3) . . ? C4 C15 C26 110.2(3) . . ? C29 C15 C26 109.1(3) . . ? C4 C15 C22 111.9(3) . . ? C29 C15 C22 107.4(3) . . ? C26 C15 C22 107.7(3) . . ? C5 C16 C24 121.6(4) . . ? C5 C16 H16 119.2 . . ? C24 C16 H16 119.2 . . ? C7 C17 H17A 109.5 . . ? C7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 C18 C8 123.4(3) . . ? N2 C18 H18 118.3 . . ? C8 C18 H18 118.3 . . ? C10 C19 C14 121.6(4) . . ? C10 C19 H19 119.2 . . ? C14 C19 H19 119.2 . . ? N1 C20 C28 111.2(3) . . ? N1 C20 C27 102.3(3) . . ? C28 C20 C27 114.3(3) . . ? N1 C20 H20 109.6 . . ? C28 C20 H20 109.6 . . ? C27 C20 H20 109.6 . . ? N1 C21 C6 101.6(3) . . ? N1 C21 C30 114.0(3) . . ? C6 C21 C30 114.2(4) . . ? N1 C21 H21 108.9 . . ? C6 C21 H21 108.9 . . ? C30 C21 H21 108.9 . . ? C15 C22 H22A 109.5 . . ? C15 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C15 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C14 C23 C11 121.2(3) . . ? C14 C23 H23 119.4 . . ? C11 C23 H23 119.4 . . ? C25 C24 C16 120.8(3) . . ? C25 C24 H24 119.6 . . ? C16 C24 H24 119.6 . . ? C24 C25 C11 121.0(3) . . ? C24 C25 H25 119.5 . . ? C11 C25 H25 119.5 . . ? C15 C26 H26A 109.5 . . ? C15 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C15 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C21 C6 C27 105.3(3) . . ? C21 C6 H6A 110.7 . . ? C27 C6 H6A 110.7 . . ? C21 C6 H6B 110.7 . . ? C27 C6 H6B 110.7 . . ? H6A C6 H6B 108.8 . . ? C6 C27 C20 106.7(3) . . ? C6 C27 H27A 110.4 . . ? C20 C27 H27A 110.4 . . ? C6 C27 H27B 110.4 . . ? C20 C27 H27B 110.4 . . ? H27A C27 H27B 108.6 . . ? C20 C28 H28A 109.5 . . ? C20 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C20 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C15 C29 H29A 109.5 . . ? C15 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C15 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C21 C30 H30A 109.5 . . ? C21 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C21 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.119 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.034