Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_JRLS2 _database_code_CSD 156612 #--------------------------------------------------------------------------- _audit_creation_date '2000-06-12' _audit_creation_method SHELXL-97 _audit_update_record ; ? ; _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Foxon, Simon P.' 'Lindsay Smith, J.' 'O'Brien, P.' 'Reginato, Gloriana' #--------------------------------------------------------------------------- # SUBMISSION DETAILS _publ_contact_author ; John R Lindsay Smith Department of Chemistry University of York Heslington York YO10 5DD UK ; _publ_contact_author_email 'jrls1@york.ac.uk' _publ_contact_author_fax '+44 (1904) 43 25 16' _publ_contact_author_phone '+44 (1904) 43 25 85' # TITLE AND AUTHOR LIST _publ_section_title ; ENTER TITLE HERE ; #---------------------------------------------------------------------- _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H38 N2 O2' _chemical_formula_weight 518.67 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' 'O' 'O' 0.0106 0.0060 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 14.101(5) _cell_length_b 23.237(5) _cell_length_c 8.945(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2931.0(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 4.55 _cell_measurement_theta_max 5.47 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.072 _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 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.05 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -5 1 0 -5 -1 0 -1 2 _diffrn_reflns_number 2933 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.3224 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2933 _reflns_number_gt 935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' _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^)+(0.0310P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2933 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2722 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1530 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0135(4) -0.2318(2) 0.2311(6) 0.0229(17) Uani 1 1 d . . . O2 O 0.0805(4) -0.3507(3) -0.1765(7) 0.0270(18) Uani 1 1 d . . . N1 N 0.1540(5) -0.1721(3) 0.0621(9) 0.029(2) Uani 1 1 d . . . H1 H 0.1200 -0.1705 0.1419 0.035 Uiso 1 1 calc R . . N2 N -0.1297(5) -0.2222(3) -0.0282(9) 0.028(2) Uani 1 1 d . . . H2 H -0.1419 -0.2576 -0.0075 0.034 Uiso 1 1 calc R . . C1 C 0.0433(6) -0.2402(3) -0.0743(11) 0.022(2) Uani 1 1 d . . . H1A H 0.0433 -0.2558 -0.1761 0.027 Uiso 1 1 calc R . . C2 C 0.1330(7) -0.2053(4) -0.0620(12) 0.026(3) Uani 1 1 d . . . C3 C 0.2045(7) -0.1957(4) -0.1625(11) 0.031(3) Uani 1 1 d . . . H3 H 0.2095 -0.2122 -0.2569 0.038 Uiso 1 1 calc R . . C4 C 0.2702(7) -0.1559(4) -0.0982(12) 0.035(3) Uani 1 1 d . . . H4 H 0.3253 -0.1421 -0.1426 0.042 Uiso 1 1 calc R . . C5 C 0.2372(7) -0.1421(4) 0.0396(14) 0.038(3) Uani 1 1 d . . . H5 H 0.2655 -0.1169 0.1069 0.045 Uiso 1 1 calc R . . C6 C -0.0432(6) -0.2015(4) -0.0654(10) 0.021(2) Uani 1 1 d . . . C7 C -0.0523(7) -0.1438(3) -0.0972(11) 0.027(3) Uani 1 1 d . . . H7 H -0.0046 -0.1190 -0.1291 0.032 Uiso 1 1 calc R . . C8 C -0.1505(7) -0.1294(4) -0.0710(11) 0.029(3) Uani 1 1 d . . . H8 H -0.1778 -0.0932 -0.0814 0.035 Uiso 1 1 calc R . . C9 C -0.1954(6) -0.1783(4) -0.0283(10) 0.028(3) Uani 1 1 d . . . H9 H -0.2592 -0.1816 -0.0036 0.033 Uiso 1 1 calc R . . C10 C 0.0400(6) -0.2930(4) 0.0295(10) 0.018(2) Uani 1 1 d . . . C11 C 0.0210(6) -0.2885(3) 0.1825(11) 0.022(2) Uani 1 1 d . . . C12 C 0.0152(6) -0.3354(3) 0.2761(11) 0.025(3) Uani 1 1 d . . . H12 H 0.0041 -0.3308 0.3778 0.030 Uiso 1 1 calc R . . C13 C 0.0263(6) -0.3894(4) 0.2150(11) 0.029(3) Uani 1 1 d . . . H13 H 0.0199 -0.4216 0.2758 0.035 Uiso 1 1 calc R . . C14 C 0.0471(6) -0.3967(4) 0.0643(11) 0.027(3) Uani 1 1 d . . . H14 H 0.0562 -0.4333 0.0251 0.032 Uiso 1 1 calc R . . C15 C 0.0539(6) -0.3481(4) -0.0279(10) 0.019(2) Uani 1 1 d . . . C16 C -0.0166(7) -0.2194(3) 0.3856(11) 0.025(3) Uani 1 1 d . . . H16 H 0.0215 -0.2426 0.4546 0.029 Uiso 1 1 calc R . . C17 C 0.0089(6) -0.1570(4) 0.4055(11) 0.023(2) Uani 1 1 d . . . C18 C -0.0208(7) -0.1164(4) 0.2992(11) 0.034(3) Uani 1 1 d . . . H18 H -0.0583 -0.1280 0.2191 0.041 Uiso 1 1 calc R . . C19 C 0.0055(8) -0.0589(4) 0.3129(12) 0.046(3) Uani 1 1 d . . . H19 H -0.0147 -0.0321 0.2425 0.055 Uiso 1 1 calc R . . C20 C 0.0612(7) -0.0419(4) 0.4306(14) 0.050(3) Uani 1 1 d . . . H20 H 0.0809 -0.0038 0.4378 0.060 Uiso 1 1 calc R . . C21 C 0.0878(7) -0.0807(4) 0.5371(12) 0.043(3) Uani 1 1 d . . . H21 H 0.1235 -0.0683 0.6184 0.052 Uiso 1 1 calc R . . C22 C 0.0622(7) -0.1389(4) 0.5261(11) 0.034(3) Uani 1 1 d . . . H22 H 0.0810 -0.1650 0.5992 0.041 Uiso 1 1 calc R . . C23 C -0.1211(6) -0.2342(4) 0.4075(10) 0.029(3) Uani 1 1 d . . . H23A H -0.1321 -0.2739 0.3783 0.035 Uiso 1 1 calc R . . H23B H -0.1597 -0.2097 0.3444 0.035 Uiso 1 1 calc R . . C24 C -0.1498(6) -0.2259(4) 0.5722(11) 0.028(3) Uani 1 1 d . . . H24A H -0.1425 -0.1857 0.5994 0.033 Uiso 1 1 calc R . . H24B H -0.1082 -0.2484 0.6357 0.033 Uiso 1 1 calc R . . C25 C -0.2542(6) -0.2447(4) 0.5985(11) 0.036(3) Uani 1 1 d . . . H25A H -0.2953 -0.2228 0.5346 0.054 Uiso 1 1 calc R . . H25B H -0.2710 -0.2380 0.7011 0.054 Uiso 1 1 calc R . . H25C H -0.2607 -0.2849 0.5762 0.054 Uiso 1 1 calc R . . C26 C 0.0927(7) -0.4061(4) -0.2476(10) 0.031(3) Uani 1 1 d . . . H26 H 0.1178 -0.4341 -0.1760 0.037 Uiso 1 1 calc R . . C27 C 0.0007(7) -0.4274(4) -0.3129(10) 0.026(3) Uani 1 1 d . . . C28 C -0.0145(7) -0.4868(4) -0.3325(11) 0.033(3) Uani 1 1 d . . . H28 H 0.0297 -0.5132 -0.2973 0.040 Uiso 1 1 calc R . . C29 C -0.0956(7) -0.5057(4) -0.4045(13) 0.047(3) Uani 1 1 d . . . H29 H -0.1032 -0.5450 -0.4203 0.057 Uiso 1 1 calc R . . C30 C -0.1663(8) -0.4684(4) -0.4543(13) 0.048(3) Uani 1 1 d . . . H30 H -0.2204 -0.4815 -0.5033 0.058 Uiso 1 1 calc R . . C31 C -0.1507(8) -0.4107(4) -0.4260(13) 0.052(3) Uani 1 1 d . . . H31 H -0.1969 -0.3845 -0.4554 0.062 Uiso 1 1 calc R . . C32 C -0.0702(7) -0.3896(4) -0.3565(10) 0.029(3) Uani 1 1 d . . . H32 H -0.0637 -0.3504 -0.3391 0.035 Uiso 1 1 calc R . . C33 C 0.1671(7) -0.3946(4) -0.3751(11) 0.032(3) Uani 1 1 d . . . H33A H 0.1392 -0.3692 -0.4490 0.038 Uiso 1 1 calc R . . H33B H 0.2218 -0.3753 -0.3329 0.038 Uiso 1 1 calc R . . C34 C 0.1993(7) -0.4495(4) -0.4514(11) 0.042(3) Uani 1 1 d . . . H34A H 0.1452 -0.4683 -0.4970 0.051 Uiso 1 1 calc R . . H34B H 0.2259 -0.4755 -0.3776 0.051 Uiso 1 1 calc R . . C35 C 0.2745(6) -0.4364(4) -0.5725(11) 0.053(3) Uani 1 1 d . . . H35A H 0.2470 -0.4125 -0.6485 0.080 Uiso 1 1 calc R . . H35B H 0.2959 -0.4718 -0.6163 0.080 Uiso 1 1 calc R . . H35C H 0.3273 -0.4168 -0.5278 0.080 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 0.026(4) 0.025(4) 0.017(4) 0.002(3) 0.005(3) 0.002(3) O2 0.042(5) 0.021(4) 0.018(4) -0.010(3) 0.001(4) 0.002(3) N1 0.023(5) 0.032(5) 0.033(5) 0.010(5) 0.003(5) 0.000(4) N2 0.025(5) 0.024(5) 0.036(6) 0.011(4) -0.005(5) -0.003(4) C1 0.013(5) 0.026(5) 0.028(6) -0.014(6) 0.006(5) 0.001(5) C2 0.035(7) 0.020(5) 0.023(6) 0.004(6) 0.001(6) 0.014(5) C3 0.034(6) 0.039(7) 0.021(6) -0.005(6) -0.003(6) -0.002(6) C4 0.029(7) 0.037(7) 0.039(8) 0.021(7) 0.012(6) 0.008(6) C5 0.025(6) 0.026(6) 0.062(9) -0.005(7) 0.000(7) -0.006(5) C6 0.025(6) 0.030(6) 0.009(5) 0.002(5) 0.005(5) -0.004(5) C7 0.032(7) 0.015(5) 0.035(6) 0.009(6) -0.001(6) 0.000(5) C8 0.031(6) 0.030(6) 0.027(7) -0.001(6) -0.003(6) 0.008(5) C9 0.016(5) 0.031(6) 0.036(7) -0.006(6) -0.012(6) 0.003(5) C10 0.024(6) 0.016(6) 0.014(6) -0.001(4) 0.003(5) -0.005(5) C11 0.020(6) 0.011(6) 0.033(6) -0.010(5) -0.007(5) 0.009(5) C12 0.026(6) 0.016(5) 0.033(6) 0.000(5) -0.008(6) -0.002(5) C13 0.038(7) 0.023(6) 0.027(6) 0.005(5) -0.001(6) 0.006(6) C14 0.039(7) 0.017(5) 0.026(6) -0.003(5) -0.003(6) -0.009(5) C15 0.007(5) 0.031(7) 0.018(6) 0.001(5) -0.003(5) 0.005(5) C16 0.031(6) 0.015(5) 0.027(6) -0.005(5) 0.001(5) -0.003(5) C17 0.022(6) 0.021(5) 0.025(6) -0.009(5) 0.006(5) 0.004(5) C18 0.043(7) 0.034(6) 0.025(6) -0.012(6) 0.006(6) 0.002(6) C19 0.058(8) 0.048(8) 0.031(7) -0.019(6) 0.001(7) 0.020(7) C20 0.052(8) 0.028(6) 0.070(10) 0.007(8) 0.013(8) -0.006(6) C21 0.042(7) 0.044(7) 0.042(8) -0.008(7) 0.005(7) -0.007(6) C22 0.025(6) 0.040(7) 0.038(7) -0.003(6) 0.001(6) 0.004(5) C23 0.041(7) 0.031(5) 0.016(6) 0.016(5) -0.003(5) 0.002(5) C24 0.026(6) 0.026(6) 0.031(7) -0.017(6) -0.001(6) 0.003(5) C25 0.039(7) 0.039(6) 0.029(7) -0.010(6) 0.013(6) 0.003(6) C26 0.044(7) 0.036(7) 0.012(6) -0.004(6) 0.003(6) 0.005(6) C27 0.039(7) 0.020(5) 0.017(6) -0.005(5) 0.012(6) 0.001(5) C28 0.025(6) 0.036(7) 0.037(7) 0.002(6) -0.001(6) 0.000(5) C29 0.053(8) 0.023(6) 0.065(9) 0.006(7) -0.002(8) -0.003(6) C30 0.043(8) 0.045(7) 0.058(9) -0.001(8) 0.005(7) 0.001(6) C31 0.026(7) 0.063(8) 0.067(10) 0.002(9) -0.007(7) 0.022(6) C32 0.032(7) 0.026(6) 0.029(7) -0.002(5) 0.004(6) 0.010(5) C33 0.031(7) 0.031(6) 0.034(7) -0.013(6) 0.001(5) -0.004(5) C34 0.060(8) 0.039(7) 0.028(7) 0.006(7) 0.016(7) 0.008(6) C35 0.066(9) 0.062(8) 0.032(7) -0.012(7) 0.017(7) -0.010(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 O1 C11 1.391(9) . ? O1 C16 1.474(10) . ? O2 C15 1.382(10) . ? O2 C26 1.447(9) . ? N1 C5 1.380(11) . ? N1 C2 1.383(11) . ? N2 C6 1.353(10) . ? N2 C9 1.380(10) . ? C1 C2 1.507(12) . ? C1 C6 1.518(11) . ? C1 C10 1.539(11) . ? C2 C3 1.370(12) . ? C3 C4 1.429(12) . ? C4 C5 1.357(14) . ? C6 C7 1.378(10) . ? C7 C8 1.443(12) . ? C8 C9 1.356(11) . ? C10 C15 1.395(11) . ? C10 C11 1.399(12) . ? C11 C12 1.377(11) . ? C12 C13 1.376(11) . ? C13 C14 1.390(12) . ? C14 C15 1.401(12) . ? C16 C17 1.505(10) . ? C16 C23 1.526(12) . ? C17 C22 1.380(12) . ? C17 C18 1.402(12) . ? C18 C19 1.393(12) . ? C19 C20 1.372(14) . ? C20 C21 1.364(13) . ? C21 C22 1.403(11) . ? C23 C24 1.540(12) . ? C24 C25 1.553(11) . ? C26 C27 1.506(12) . ? C26 C33 1.572(11) . ? C27 C32 1.386(12) . ? C27 C28 1.409(11) . ? C28 C29 1.383(12) . ? C29 C30 1.395(13) . ? C30 C31 1.383(12) . ? C31 C32 1.383(12) . ? C33 C34 1.516(11) . ? C34 C35 1.546(11) . ? 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 C11 O1 C16 120.0(7) . . ? C15 O2 C26 119.6(7) . . ? C5 N1 C2 110.2(9) . . ? C6 N2 C9 110.0(7) . . ? C2 C1 C6 110.6(7) . . ? C2 C1 C10 114.2(8) . . ? C6 C1 C10 114.6(7) . . ? C3 C2 N1 106.2(8) . . ? C3 C2 C1 131.1(9) . . ? N1 C2 C1 122.5(9) . . ? C2 C3 C4 108.6(9) . . ? C5 C4 C3 107.3(9) . . ? C4 C5 N1 107.7(10) . . ? N2 C6 C7 108.2(8) . . ? N2 C6 C1 121.8(8) . . ? C7 C6 C1 129.9(9) . . ? C6 C7 C8 106.4(8) . . ? C9 C8 C7 107.5(8) . . ? C8 C9 N2 107.9(8) . . ? C15 C10 C11 117.1(8) . . ? C15 C10 C1 120.4(8) . . ? C11 C10 C1 122.5(8) . . ? C12 C11 O1 123.8(8) . . ? C12 C11 C10 123.1(8) . . ? O1 C11 C10 113.0(8) . . ? C13 C12 C11 118.3(9) . . ? C12 C13 C14 121.3(9) . . ? C13 C14 C15 119.2(9) . . ? O2 C15 C10 115.6(8) . . ? O2 C15 C14 123.4(9) . . ? C10 C15 C14 120.9(8) . . ? O1 C16 C17 103.3(7) . . ? O1 C16 C23 110.8(7) . . ? C17 C16 C23 115.7(8) . . ? C22 C17 C18 119.2(8) . . ? C22 C17 C16 121.0(9) . . ? C18 C17 C16 119.7(9) . . ? C19 C18 C17 120.4(10) . . ? C20 C19 C18 119.7(11) . . ? C21 C20 C19 120.3(10) . . ? C20 C21 C22 121.1(11) . . ? C17 C22 C21 119.2(10) . . ? C16 C23 C24 110.4(8) . . ? C23 C24 C25 111.0(8) . . ? O2 C26 C27 111.2(8) . . ? O2 C26 C33 104.4(7) . . ? C27 C26 C33 110.4(7) . . ? C32 C27 C28 118.4(10) . . ? C32 C27 C26 121.5(8) . . ? C28 C27 C26 120.1(9) . . ? C29 C28 C27 119.7(10) . . ? C28 C29 C30 122.8(10) . . ? C31 C30 C29 115.5(11) . . ? C30 C31 C32 123.8(10) . . ? C31 C32 C27 119.6(9) . . ? C34 C33 C26 112.6(8) . . ? C33 C34 C35 110.9(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.290 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.069