# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jones, R.' _publ_contact_author_name 'Jones, R.' _publ_contact_author_email r.c.f.jones@lboro.ac.uk _publ_section_title ; Cycloaddition of Homochiral Dihydroimidazoles: A 1,3-Dipolar Cycloaddition Route to Optically Active Pyrrolo[1,2-a]imidazoles ; # Attachment '- Paper1_9g.cif' data_3js2 _database_code_depnum_ccdc_archive 'CCDC 787234' #TrackingRef '- Paper1_9g.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H34 N2 O4' _chemical_formula_weight 450.56 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 8.0460(10) _cell_length_b 14.280(2) _cell_length_c 22.646(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2602.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 51 _cell_measurement_theta_min 10 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.59 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.150 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9481 _exptl_absorpt_correction_T_max 0.9773 _exptl_absorpt_process_details ? _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 P4 _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2631 _diffrn_reflns_av_R_equivalents 0.2758 _diffrn_reflns_av_sigmaI/netI 0.0609 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2620 _reflns_number_gt 1393 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0601P)^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 SHELXL _refine_ls_extinction_coef 0.0067(12) _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 9(2) _refine_ls_number_reflns 2620 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1034 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 0.807 _refine_ls_restrained_S_all 0.807 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 -0.2866(4) -0.47670(18) -0.01322(11) 0.0455(7) Uani 1 1 d . . . C2 C -0.1996(5) -0.4484(2) 0.04008(15) 0.0555(10) Uani 1 1 d . . . H2A H -0.2265 -0.3843 0.0506 0.067 Uiso 1 1 calc R . . H2B H -0.0802 -0.4539 0.0351 0.067 Uiso 1 1 calc R . . C3 C -0.2626(5) -0.5165(2) 0.08646(14) 0.0533(10) Uani 1 1 d . . . H3A H -0.3706 -0.4951 0.1012 0.064 Uiso 1 1 calc R . . N4 N -0.2850(4) -0.60271(19) 0.05230(10) 0.0458(7) Uani 1 1 d . . . C5 C -0.4335(5) -0.6597(2) 0.06524(14) 0.0513(10) Uani 1 1 d . . . H5A H -0.5266 -0.6197 0.0773 0.062 Uiso 1 1 calc R . . C6 C -0.4696(5) -0.7060(2) 0.00644(14) 0.0561(10) Uani 1 1 d . . . H6A H -0.5850 -0.7251 0.0041 0.067 Uiso 1 1 calc R . . H6B H -0.3995 -0.7605 0.0008 0.067 Uiso 1 1 calc R . . C7 C -0.4308(4) -0.6306(2) -0.03995(14) 0.0476(9) Uani 1 1 d . . . C7A C -0.2824(4) -0.5789(2) -0.01102(14) 0.0472(9) Uani 1 1 d . . . H7AA H -0.1783 -0.6013 -0.0286 0.057 Uiso 1 1 calc R . . C10 C -0.2068(5) -0.4406(3) -0.06702(15) 0.0610(11) Uani 1 1 d . . . H10A H -0.2605 -0.4680 -0.1013 0.073 Uiso 1 1 calc R . . H10B H -0.0912 -0.4598 -0.0674 0.073 Uiso 1 1 calc R . . C11 C -0.2156(5) -0.3346(3) -0.07163(15) 0.0549(10) Uani 1 1 d . . . C12 C -0.3438(5) -0.2926(3) -0.10080(16) 0.0656(11) Uani 1 1 d . . . H12A H -0.4258 -0.3297 -0.1178 0.079 Uiso 1 1 calc R . . C13 C -0.3555(6) -0.1959(3) -0.10589(19) 0.0772(13) Uani 1 1 d . . . H13A H -0.4431 -0.1685 -0.1264 0.093 Uiso 1 1 calc R . . C14 C -0.2355(7) -0.1421(3) -0.0802(2) 0.0827(15) Uani 1 1 d . . . H14A H -0.2414 -0.0772 -0.0833 0.099 Uiso 1 1 calc R . . C15 C -0.1074(7) -0.1820(3) -0.0501(2) 0.0828(14) Uani 1 1 d . . . H15A H -0.0281 -0.1445 -0.0318 0.099 Uiso 1 1 calc R . . C16 C -0.0956(6) -0.2779(3) -0.04666(17) 0.0708(12) Uani 1 1 d . . . H16A H -0.0056 -0.3049 -0.0273 0.085 Uiso 1 1 calc R . . C31 C -0.1419(5) -0.5254(3) 0.13770(15) 0.0572(10) Uani 1 1 d . . . C32 C -0.1749(7) -0.4821(3) 0.19062(17) 0.0946(16) Uani 1 1 d . . . H32A H -0.2751 -0.4510 0.1966 0.114 Uiso 1 1 calc R . . C33 C -0.0534(9) -0.4856(5) 0.2359(2) 0.115(2) Uani 1 1 d . . . H33A H -0.0734 -0.4562 0.2719 0.138 Uiso 1 1 calc R . . C34 C 0.0916(9) -0.5315(4) 0.2270(2) 0.1138(19) Uani 1 1 d . . . H34A H 0.1704 -0.5333 0.2571 0.137 Uiso 1 1 calc R . . C35 C 0.1232(6) -0.5745(4) 0.1755(2) 0.0962(16) Uani 1 1 d . . . H35A H 0.2234 -0.6059 0.1701 0.115 Uiso 1 1 calc R . . C36 C 0.0089(6) -0.5724(3) 0.13087(18) 0.0711(12) Uani 1 1 d . . . H36A H 0.0319 -0.6026 0.0954 0.085 Uiso 1 1 calc R . . C51 C -0.3925(5) -0.7308(3) 0.11361(17) 0.0631(11) Uani 1 1 d . . . O51 O -0.3185(5) -0.8023(2) 0.10575(13) 0.0995(11) Uani 1 1 d . . . O52 O -0.4437(4) -0.6998(2) 0.16540(11) 0.0794(9) Uani 1 1 d . . . C52 C -0.4070(7) -0.7515(4) 0.22134(19) 0.0964(17) Uani 1 1 d . . . C53 C -0.2252(6) -0.7609(4) 0.2297(2) 0.1112(19) Uani 1 1 d . . . H53A H -0.1756 -0.6999 0.2318 0.167 Uiso 1 1 calc R . . H53B H -0.1786 -0.7948 0.1970 0.167 Uiso 1 1 calc R . . H53C H -0.2035 -0.7943 0.2657 0.167 Uiso 1 1 calc R . . C54 C -0.4920(10) -0.8460(5) 0.2179(3) 0.184(4) Uani 1 1 d . . . H54A H -0.4396 -0.8834 0.1880 0.277 Uiso 1 1 calc R . . H54B H -0.6072 -0.8374 0.2082 0.277 Uiso 1 1 calc R . . H54C H -0.4831 -0.8771 0.2553 0.277 Uiso 1 1 calc R . . C55 C -0.4795(10) -0.6876(6) 0.2668(2) 0.195(4) Uani 1 1 d . . . H55A H -0.4203 -0.6293 0.2667 0.293 Uiso 1 1 calc R . . H55B H -0.4704 -0.7162 0.3051 0.293 Uiso 1 1 calc R . . H55C H -0.5945 -0.6764 0.2579 0.293 Uiso 1 1 calc R . . C71 C -0.3850(5) -0.6750(3) -0.09970(15) 0.0661(12) Uani 1 1 d . . . H71A H -0.4806 -0.7061 -0.1158 0.099 Uiso 1 1 calc R . . H71B H -0.2972 -0.7196 -0.0941 0.099 Uiso 1 1 calc R . . H71C H -0.3487 -0.6270 -0.1264 0.099 Uiso 1 1 calc R . . O71 O -0.6810(4) -0.5536(2) -0.00670(12) 0.0778(9) Uani 1 1 d . . . O72 O -0.5813(3) -0.51857(19) -0.09576(11) 0.0714(8) Uani 1 1 d . . . C72 C -0.5791(5) -0.5645(3) -0.04363(17) 0.0567(10) Uani 1 1 d . . . C73 C -0.7241(6) -0.4550(3) -0.1013(2) 0.1065(18) Uani 1 1 d . . . H73A H -0.7202 -0.4241 -0.1389 0.160 Uiso 1 1 calc R . . H73B H -0.7201 -0.4091 -0.0703 0.160 Uiso 1 1 calc R . . H73C H -0.8254 -0.4902 -0.0982 0.160 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 0.0531(18) 0.0412(17) 0.0423(16) 0.0031(14) -0.0005(15) -0.0036(16) C2 0.063(2) 0.049(2) 0.055(2) 0.0026(18) -0.004(2) -0.001(2) C3 0.062(3) 0.051(2) 0.0472(19) -0.0066(18) 0.0001(19) 0.001(2) N4 0.0509(18) 0.0512(17) 0.0354(15) -0.0009(14) 0.0010(15) -0.0007(17) C5 0.053(2) 0.050(2) 0.051(2) 0.0070(18) -0.0022(19) 0.001(2) C6 0.053(2) 0.056(2) 0.059(2) 0.001(2) -0.0039(19) -0.011(2) C7 0.047(2) 0.050(2) 0.046(2) -0.0020(18) -0.0067(19) -0.003(2) C7A 0.047(2) 0.056(2) 0.0391(19) 0.0040(18) 0.0018(19) 0.001(2) C10 0.064(3) 0.058(2) 0.061(2) -0.002(2) 0.006(2) -0.009(2) C11 0.060(3) 0.055(2) 0.050(2) 0.0106(19) 0.000(2) -0.005(2) C12 0.066(3) 0.074(3) 0.057(2) 0.002(2) -0.001(2) -0.002(2) C13 0.083(4) 0.079(3) 0.070(3) 0.012(3) 0.002(3) 0.016(3) C14 0.105(4) 0.063(3) 0.080(3) 0.013(3) 0.018(3) 0.010(3) C15 0.096(4) 0.066(3) 0.087(3) 0.008(3) 0.000(3) -0.019(3) C16 0.067(3) 0.069(3) 0.076(3) 0.015(2) -0.009(2) -0.009(3) C31 0.076(3) 0.053(2) 0.043(2) -0.005(2) 0.000(2) -0.013(2) C32 0.121(4) 0.107(4) 0.056(2) -0.029(3) 0.005(3) -0.003(4) C33 0.147(5) 0.143(5) 0.055(3) -0.040(3) -0.016(4) -0.008(5) C34 0.141(6) 0.120(5) 0.081(4) -0.001(4) -0.037(4) -0.006(5) C35 0.097(4) 0.110(4) 0.082(3) 0.001(3) -0.024(3) 0.002(3) C36 0.078(3) 0.074(3) 0.061(2) -0.003(2) -0.018(3) 0.001(3) C51 0.062(3) 0.073(3) 0.054(3) 0.007(2) 0.008(2) 0.000(3) O51 0.149(3) 0.080(2) 0.0703(19) 0.0118(18) 0.011(2) 0.033(2) O52 0.081(2) 0.107(2) 0.0503(16) 0.0210(16) 0.0120(15) 0.028(2) C52 0.093(4) 0.142(5) 0.054(3) 0.032(3) 0.012(3) 0.029(4) C53 0.109(4) 0.146(5) 0.078(3) 0.039(3) -0.011(3) 0.025(4) C54 0.169(6) 0.249(8) 0.135(5) 0.127(6) -0.025(5) -0.091(7) C55 0.213(7) 0.318(10) 0.054(3) 0.024(5) 0.038(4) 0.144(8) C71 0.075(3) 0.073(3) 0.051(2) -0.008(2) -0.007(2) -0.010(2) O71 0.0668(19) 0.095(2) 0.0711(18) -0.0035(17) 0.0050(17) 0.0120(18) O72 0.0632(18) 0.0813(18) 0.0698(18) 0.0119(16) -0.0138(15) 0.0067(17) C72 0.056(3) 0.066(3) 0.048(2) 0.001(2) -0.008(2) -0.012(2) C73 0.085(3) 0.115(4) 0.119(4) 0.017(3) -0.027(3) 0.046(3) _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 C2 1.453(4) . ? N1 C7A 1.460(4) . ? N1 C10 1.470(4) . ? C2 C3 1.518(5) . ? C3 N4 1.465(4) . ? C3 C31 1.519(5) . ? N4 C7A 1.474(4) . ? N4 C5 1.475(4) . ? C5 C6 1.515(4) . ? C5 C51 1.530(5) . ? C6 C7 1.536(4) . ? C7 C72 1.524(5) . ? C7 C71 1.539(5) . ? C7 C7A 1.549(5) . ? C10 C11 1.519(5) . ? C11 C12 1.364(5) . ? C11 C16 1.381(5) . ? C12 C13 1.388(6) . ? C13 C14 1.364(6) . ? C14 C15 1.362(6) . ? C15 C16 1.375(6) . ? C31 C32 1.375(5) . ? C31 C36 1.394(5) . ? C32 C33 1.418(7) . ? C33 C34 1.353(7) . ? C34 C35 1.345(6) . ? C35 C36 1.366(5) . ? C51 O51 1.196(4) . ? C51 O52 1.319(4) . ? O52 C52 1.495(5) . ? C52 C53 1.481(7) . ? C52 C55 1.494(7) . ? C52 C54 1.515(8) . ? O71 C72 1.181(4) . ? O72 C72 1.350(4) . ? O72 C73 1.470(5) . ? 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 N1 C7A 103.8(3) . . ? C2 N1 C10 112.4(3) . . ? C7A N1 C10 111.6(3) . . ? N1 C2 C3 103.6(3) . . ? N4 C3 C31 114.3(3) . . ? N4 C3 C2 102.3(3) . . ? C31 C3 C2 111.6(3) . . ? C3 N4 C7A 108.5(2) . . ? C3 N4 C5 117.3(3) . . ? C7A N4 C5 109.4(3) . . ? N4 C5 C6 102.8(3) . . ? N4 C5 C51 109.5(3) . . ? C6 C5 C51 112.4(3) . . ? C5 C6 C7 104.9(3) . . ? C72 C7 C6 108.2(3) . . ? C72 C7 C71 113.2(3) . . ? C6 C7 C71 111.2(3) . . ? C72 C7 C7A 109.4(3) . . ? C6 C7 C7A 101.6(3) . . ? C71 C7 C7A 112.6(3) . . ? N1 C7A N4 105.3(3) . . ? N1 C7A C7 116.3(3) . . ? N4 C7A C7 106.9(3) . . ? N1 C10 C11 112.7(3) . . ? C12 C11 C16 118.0(4) . . ? C12 C11 C10 120.5(4) . . ? C16 C11 C10 121.5(4) . . ? C11 C12 C13 121.9(4) . . ? C14 C13 C12 118.5(4) . . ? C13 C14 C15 120.9(4) . . ? C14 C15 C16 119.9(5) . . ? C15 C16 C11 120.8(4) . . ? C32 C31 C36 118.8(4) . . ? C32 C31 C3 120.3(4) . . ? C36 C31 C3 120.8(3) . . ? C31 C32 C33 118.8(5) . . ? C34 C33 C32 120.3(5) . . ? C35 C34 C33 120.9(5) . . ? C34 C35 C36 120.3(5) . . ? C35 C36 C31 121.0(4) . . ? O51 C51 O52 125.0(4) . . ? O51 C51 C5 124.6(4) . . ? O52 C51 C5 110.3(4) . . ? C51 O52 C52 121.7(3) . . ? C53 C52 O52 110.4(4) . . ? C53 C52 C55 110.7(5) . . ? O52 C52 C55 101.9(4) . . ? C53 C52 C54 111.8(5) . . ? O52 C52 C54 107.8(4) . . ? C55 C52 C54 113.7(6) . . ? C72 O72 C73 112.6(3) . . ? O71 C72 O72 123.1(4) . . ? O71 C72 C7 125.9(4) . . ? O72 C72 C7 111.0(3) . . ? 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 C7A N1 C2 C3 -41.1(3) . . . . ? C10 N1 C2 C3 -161.8(3) . . . . ? N1 C2 C3 N4 34.5(4) . . . . ? N1 C2 C3 C31 157.2(3) . . . . ? C31 C3 N4 C7A -136.1(3) . . . . ? C2 C3 N4 C7A -15.3(4) . . . . ? C31 C3 N4 C5 99.3(4) . . . . ? C2 C3 N4 C5 -139.8(3) . . . . ? C3 N4 C5 C6 150.3(3) . . . . ? C7A N4 C5 C6 26.2(3) . . . . ? C3 N4 C5 C51 -90.0(4) . . . . ? C7A N4 C5 C51 145.9(3) . . . . ? N4 C5 C6 C7 -37.9(3) . . . . ? C51 C5 C6 C7 -155.5(3) . . . . ? C5 C6 C7 C72 -80.4(3) . . . . ? C5 C6 C7 C71 154.6(3) . . . . ? C5 C6 C7 C7A 34.7(4) . . . . ? C2 N1 C7A N4 31.3(4) . . . . ? C10 N1 C7A N4 152.6(3) . . . . ? C2 N1 C7A C7 149.4(3) . . . . ? C10 N1 C7A C7 -89.3(4) . . . . ? C3 N4 C7A N1 -9.3(4) . . . . ? C5 N4 C7A N1 119.8(3) . . . . ? C3 N4 C7A C7 -133.6(3) . . . . ? C5 N4 C7A C7 -4.6(4) . . . . ? C72 C7 C7A N1 -21.6(4) . . . . ? C6 C7 C7A N1 -135.8(3) . . . . ? C71 C7 C7A N1 105.2(4) . . . . ? C72 C7 C7A N4 95.6(3) . . . . ? C6 C7 C7A N4 -18.6(3) . . . . ? C71 C7 C7A N4 -137.6(3) . . . . ? C2 N1 C10 C11 -66.2(4) . . . . ? C7A N1 C10 C11 177.7(3) . . . . ? N1 C10 C11 C12 -92.2(4) . . . . ? N1 C10 C11 C16 87.8(5) . . . . ? C16 C11 C12 C13 0.2(6) . . . . ? C10 C11 C12 C13 -179.9(4) . . . . ? C11 C12 C13 C14 -0.8(7) . . . . ? C12 C13 C14 C15 -0.2(7) . . . . ? C13 C14 C15 C16 1.8(7) . . . . ? C14 C15 C16 C11 -2.4(7) . . . . ? C12 C11 C16 C15 1.4(6) . . . . ? C10 C11 C16 C15 -178.5(4) . . . . ? N4 C3 C31 C32 -140.5(4) . . . . ? C2 C3 C31 C32 103.9(4) . . . . ? N4 C3 C31 C36 43.7(5) . . . . ? C2 C3 C31 C36 -71.9(5) . . . . ? C36 C31 C32 C33 0.9(7) . . . . ? C3 C31 C32 C33 -174.9(4) . . . . ? C31 C32 C33 C34 -0.5(9) . . . . ? C32 C33 C34 C35 0.0(10) . . . . ? C33 C34 C35 C36 0.1(9) . . . . ? C34 C35 C36 C31 0.3(7) . . . . ? C32 C31 C36 C35 -0.9(6) . . . . ? C3 C31 C36 C35 175.0(4) . . . . ? N4 C5 C51 O51 -78.8(5) . . . . ? C6 C5 C51 O51 34.7(6) . . . . ? N4 C5 C51 O52 98.4(4) . . . . ? C6 C5 C51 O52 -148.0(3) . . . . ? O51 C51 O52 C52 2.5(7) . . . . ? C5 C51 O52 C52 -174.7(4) . . . . ? C51 O52 C52 C53 59.1(6) . . . . ? C51 O52 C52 C55 176.7(5) . . . . ? C51 O52 C52 C54 -63.3(6) . . . . ? C73 O72 C72 O71 -0.5(5) . . . . ? C73 O72 C72 C7 179.2(3) . . . . ? C6 C7 C72 O71 21.5(5) . . . . ? C71 C7 C72 O71 145.2(4) . . . . ? C7A C7 C72 O71 -88.4(4) . . . . ? C6 C7 C72 O72 -158.2(3) . . . . ? C71 C7 C72 O72 -34.5(4) . . . . ? C7A C7 C72 O72 91.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.141 _refine_diff_density_min -0.127 _refine_diff_density_rms 0.029 # Attachment '- Paper1_13a.cif' data_OU2JSS _database_code_depnum_ccdc_archive 'CCDC 787235' #TrackingRef '- Paper1_13a.cif' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C26 H32 N2 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum ? _chemical_formula_weight 436.54 _chemical_melting_point ? _chemical_compound_source ? 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 10.276(2) _cell_length_b 5.799(3) _cell_length_c 20.259(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.07(2) _cell_angle_gamma 90.00 _cell_volume 1176.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150.0(2) _cell_measurement_reflns_used 34 _cell_measurement_theta_min 8.0 _cell_measurement_theta_max 12.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method ? _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(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 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega-2theta _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 'variation +/- 6' _diffrn_reflns_number 2820 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0809 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2284 _reflns_number_observed 1639 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Stoe STADI-4 (Stoe & Cie, 1996a)' _computing_cell_refinement 'Stoe STADI-4 (Stoe & Cie, 1996a)' _computing_data_reduction 'Stoe X-RED (Stoe & Cie, 1996b)' _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1994)' _computing_publication_material 'SHELXS-96 (Sheldrick, 1990)' _refine_special_details ; Refinement of F^2^ against ALL reflections. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+2.20P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0054(12) _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 1(4) _refine_ls_number_reflns 2284 _refine_ls_number_parameters 284 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.1226 _refine_ls_R_factor_obs 0.0734 _refine_ls_wR_factor_all 0.1465 _refine_ls_wR_factor_obs 0.1170 _refine_ls_goodness_of_fit_all 1.253 _refine_ls_goodness_of_fit_obs 1.213 _refine_ls_restrained_S_all 1.249 _refine_ls_restrained_S_obs 1.207 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.1979(5) 0.3844(12) 0.3493(3) 0.0227(14) Uani 1 d . . C2 C 0.3240(7) 0.2862(15) 0.3394(3) 0.0261(18) Uani 1 d . . H2A H 0.3477 0.1434 0.3662 0.031 Uiso 1 calc R . H2B H 0.3983 0.3981 0.3518 0.031 Uiso 1 calc R . C3 C 0.2910(6) 0.2359(15) 0.2635(3) 0.0237(17) Uani 1 d . . H3A H 0.2347 0.0937 0.2545 0.028 Uiso 1 calc R . N4 N 0.2090(5) 0.4377(12) 0.2365(3) 0.0221(15) Uani 1 d . . C5 C 0.1091(6) 0.3987(14) 0.1722(3) 0.0206(16) Uani 1 d . . H5A H 0.0937 0.2300 0.1636 0.025 Uiso 1 calc R . C6 C -0.0183(7) 0.5164(16) 0.1838(3) 0.0284(18) Uani 1 d . . H6A H -0.0993 0.4415 0.1564 0.034 Uiso 1 calc R . H6B H -0.0196 0.6819 0.1717 0.034 Uiso 1 calc R . C7 C -0.0105(7) 0.4852(14) 0.2602(4) 0.0254(18) Uani 1 d . . H7A H -0.0639 0.6060 0.2775 0.030 Uiso 1 calc R . C7A C 0.1412(6) 0.5216(14) 0.2887(3) 0.0211(16) Uani 1 d . . H7AA H 0.1609 0.6889 0.2979 0.025 Uiso 1 calc R . C C 0.2120(4) 0.5253(9) 0.4116(2) 0.0315(19) Uani 1 d . . H0A H 0.1267 0.6047 0.4117 0.038 Uiso 1 calc R . H0B H 0.2821 0.6436 0.4133 0.038 Uiso 1 calc R . C11P C 0.2502(4) 0.3638(9) 0.4738(2) 0.0305(19) Uani 1 d RD . C12P C 0.3661(4) 0.4040(9) 0.5231(2) 0.034(2) Uani 1 d RD . H12A H 0.4243 0.5266 0.5178 0.040 Uiso 1 calc R . C13P C 0.3966(7) 0.2622(12) 0.5806(3) 0.038(2) Uani 1 d D . H13A H 0.4755 0.2895 0.6145 0.046 Uiso 1 calc R . C14P C 0.3126(6) 0.0832(14) 0.5883(4) 0.040(2) Uani 1 d D . H14A H 0.3345 -0.0136 0.6271 0.048 Uiso 1 calc R . C15P C 0.1966(7) 0.0446(15) 0.5395(3) 0.040(2) Uani 1 d D . H15A H 0.1377 -0.0767 0.5449 0.049 Uiso 1 calc R . C16P C 0.1671(7) 0.1859(13) 0.4823(3) 0.037(2) Uani 1 d D . H16A H 0.0880 0.1585 0.4485 0.045 Uiso 1 calc R . C31P C 0.4108(6) 0.2091(10) 0.2320(3) 0.0254(18) Uani 1 d D . C32P C 0.4294(6) 0.0073(14) 0.1991(3) 0.032(2) Uani 1 d D . H32A H 0.3674 -0.1156 0.1966 0.038 Uiso 1 calc R . C33P C 0.5391(7) -0.0170(16) 0.1696(3) 0.042(2) Uani 1 d D . H33A H 0.5515 -0.1558 0.1469 0.050 Uiso 1 calc R . C34P C 0.6294(7) 0.1619(12) 0.1736(3) 0.040(3) Uani 1 d D . H34A H 0.7043 0.1456 0.1538 0.049 Uiso 1 calc R . C35P C 0.6112(6) 0.3651(17) 0.2064(3) 0.036(2) Uani 1 d D . H35A H 0.6733 0.4881 0.2092 0.043 Uiso 1 calc R . C36P C 0.5010(6) 0.3877(15) 0.2355(3) 0.0307(19) Uani 1 d D . H36A H 0.4880 0.5270 0.2578 0.037 Uiso 1 calc R . O51 O 0.1647(5) 0.7180(10) 0.1065(2) 0.0296(13) Uani 1 d . . C51 C 0.1566(7) 0.5129(16) 0.1134(3) 0.0219(17) Uani 1 d . . O52 O 0.1869(5) 0.3494(10) 0.0727(2) 0.0286(13) Uani 1 d . . C52 C 0.2346(7) 0.4146(15) 0.0104(3) 0.0272(18) Uani 1 d . . C53 C 0.2569(9) 0.1778(17) -0.0172(4) 0.044(2) Uani 1 d . . H53A H 0.3280 0.0979 0.0151 0.066 Uiso 1 calc R . H53B H 0.2829 0.1949 -0.0606 0.066 Uiso 1 calc R . H53C H 0.1742 0.0880 -0.0239 0.066 Uiso 1 calc R . C54 C 0.3648(6) 0.5426(16) 0.0310(4) 0.033(2) Uani 1 d . . H54A H 0.4304 0.4456 0.0613 0.049 Uiso 1 calc R . H54B H 0.3510 0.6850 0.0545 0.049 Uiso 1 calc R . H54C H 0.3978 0.5805 -0.0095 0.049 Uiso 1 calc R . C55 C 0.1249(7) 0.5464(17) -0.0369(3) 0.035(2) Uani 1 d . . H55A H 0.0440 0.4514 -0.0480 0.052 Uiso 1 calc R . H55B H 0.1536 0.5844 -0.0785 0.052 Uiso 1 calc R . H55C H 0.1060 0.6889 -0.0148 0.052 Uiso 1 calc R . O71 O -0.0349(5) 0.0723(10) 0.2489(2) 0.0300(14) Uani 1 d . . C71 C -0.0514(7) 0.2485(15) 0.2769(3) 0.0237(17) Uani 1 d . . O72 O -0.1115(5) 0.2550(10) 0.3300(2) 0.0296(13) Uani 1 d . . C72 C -0.1583(8) 0.0340(17) 0.3483(4) 0.040(2) Uani 1 d . . H72A H -0.1999 0.0536 0.3870 0.060 Uiso 1 calc R . H72B H -0.0827 -0.0725 0.3607 0.060 Uiso 1 calc R . H72C H -0.2241 -0.0287 0.3098 0.060 Uiso 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 0.026(3) 0.024(4) 0.018(3) 0.003(3) 0.005(2) -0.001(3) C2 0.025(4) 0.031(5) 0.021(4) 0.001(4) 0.002(3) 0.005(4) C3 0.019(3) 0.029(5) 0.023(4) 0.000(4) 0.003(3) 0.000(4) N4 0.020(3) 0.030(4) 0.017(3) -0.003(3) 0.006(2) 0.004(3) C5 0.024(3) 0.019(4) 0.018(3) -0.005(3) 0.002(3) -0.006(4) C6 0.028(4) 0.032(5) 0.024(4) 0.007(4) 0.004(3) -0.001(4) C7 0.022(4) 0.022(5) 0.033(4) 0.005(4) 0.009(3) 0.001(4) C7A 0.024(4) 0.020(4) 0.019(3) 0.005(3) 0.005(3) -0.005(4) C 0.034(4) 0.033(5) 0.028(4) 0.003(4) 0.008(3) 0.003(4) C11P 0.033(4) 0.039(5) 0.022(4) -0.001(4) 0.009(3) -0.009(4) C12P 0.027(4) 0.044(6) 0.031(4) -0.010(5) 0.010(3) -0.005(4) C13P 0.029(4) 0.056(6) 0.025(4) 0.006(5) -0.002(3) 0.003(5) C14P 0.037(5) 0.048(6) 0.032(4) 0.004(5) 0.000(4) 0.012(5) C15P 0.044(5) 0.042(6) 0.034(4) 0.009(5) 0.008(4) -0.005(5) C16P 0.039(5) 0.045(6) 0.022(4) 0.004(4) -0.005(3) -0.014(5) C31P 0.019(4) 0.035(5) 0.019(4) 0.001(4) -0.001(3) 0.000(4) C32P 0.026(4) 0.034(5) 0.033(4) -0.008(4) 0.000(3) -0.004(4) C33P 0.031(4) 0.057(7) 0.038(5) -0.013(5) 0.008(4) 0.005(5) C34P 0.019(4) 0.074(8) 0.031(4) -0.008(5) 0.010(3) 0.009(5) C35P 0.021(4) 0.056(6) 0.030(4) 0.002(5) 0.005(3) -0.001(5) C36P 0.024(4) 0.046(5) 0.022(4) -0.001(4) 0.006(3) -0.004(4) O51 0.037(3) 0.022(4) 0.031(3) 0.002(3) 0.010(2) -0.006(3) C51 0.019(4) 0.032(5) 0.014(3) -0.004(4) 0.002(3) -0.005(4) O52 0.030(3) 0.037(4) 0.019(2) 0.001(3) 0.007(2) -0.002(3) C52 0.031(4) 0.032(5) 0.023(4) 0.002(4) 0.015(3) -0.006(4) C53 0.054(5) 0.047(6) 0.037(5) -0.008(5) 0.021(4) -0.001(5) C54 0.026(4) 0.042(5) 0.031(4) 0.009(4) 0.008(3) -0.001(4) C55 0.033(4) 0.052(6) 0.020(4) 0.001(4) 0.007(3) -0.006(5) O71 0.038(3) 0.024(4) 0.032(3) -0.006(3) 0.017(2) -0.004(3) C71 0.023(4) 0.025(5) 0.022(4) -0.005(4) 0.003(3) -0.002(4) O72 0.033(3) 0.034(3) 0.025(3) 0.001(3) 0.015(2) -0.004(3) C72 0.049(5) 0.039(6) 0.039(5) -0.002(5) 0.023(4) -0.014(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7A 1.4685(82) . Yes N1 C2 1.4703(83) . Yes N1 C 1.4831(68) . Yes C2 C3 1.5255(86) . Yes C3 N4 1.4731(93) . Yes C3 C31P 1.5174(89) . Yes N4 C7A 1.4747(80) . Yes N4 C5 1.4818(75) . Yes C5 C51 1.5344(93) . Yes C5 C6 1.5413(92) . Yes C6 C7 1.5434(91) . Yes C7 C71 1.4959(108) . Yes C7 C7A 1.5500(88) . Yes C C11P 1.5470(90) . Yes C11P C16P 1.3745(68) . ? C11P C12P 1.3900(70) . ? C12P C13P 1.4031(75) . ? C13P C14P 1.3810(85) . ? C14P C15P 1.3842(77) . ? C15P C16P 1.3957(81) . ? C31P C32P 1.3810(80) . ? C31P C36P 1.3817(78) . ? C32P C33P 1.3967(78) . ? C33P C34P 1.3824(87) . ? C34P C35P 1.3864(87) . ? C35P C36P 1.3947(76) . ? O51 C51 1.2025(101) . Yes C51 O52 1.3389(93) . Yes O52 C52 1.5028(75) . Yes C52 C54 1.5037(98) . Yes C52 C55 1.5113(102) . Yes C52 C53 1.5193(119) . Yes O71 C71 1.1992(91) . Yes C71 O72 1.3571(78) . Yes O72 C72 1.4470(103) . Yes 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 C7A N1 C2 106.9(5) . . Yes C7A N1 C 110.9(5) . . Yes C2 N1 C 114.2(5) . . Yes N1 C2 C3 102.1(5) . . Yes N4 C3 C31P 112.0(6) . . Yes N4 C3 C2 101.6(6) . . Yes C31P C3 C2 115.2(5) . . Yes C3 N4 C7A 108.5(5) . . Yes C3 N4 C5 115.5(6) . . Yes C7A N4 C5 109.6(5) . . Yes N4 C5 C51 109.7(5) . . Yes N4 C5 C6 104.0(5) . . Yes C51 C5 C6 110.9(6) . . Yes C5 C6 C7 104.4(5) . . Yes C71 C7 C6 112.3(7) . . Yes C71 C7 C7A 110.6(6) . . Yes C6 C7 C7A 100.2(5) . . Yes N1 C7A N4 105.0(6) . . Yes N1 C7A C7 114.4(5) . . Yes N4 C7A C7 106.7(5) . . Yes N1 C C11P 108.5(3) . . Yes C16P C11P C12P 119.4(3) . . ? C16P C11P C 120.4(3) . . Yes C12P C11P C 120.1(3) . . Yes C11P C12P C13P 119.6(4) . . ? C14P C13P C12P 120.4(6) . . ? C13P C14P C15P 120.0(8) . . ? C14P C15P C16P 119.2(7) . . ? C11P C16P C15P 121.4(6) . . ? C32P C31P C36P 119.7(7) . . ? C32P C31P C3 120.3(6) . . Yes C36P C31P C3 120.1(6) . . Yes C31P C32P C33P 120.4(7) . . ? C34P C33P C32P 119.7(8) . . ? C33P C34P C35P 120.3(7) . . ? C34P C35P C36P 119.5(7) . . ? C31P C36P C35P 120.5(7) . . ? O51 C51 O52 126.6(7) . . Yes O51 C51 C5 124.1(7) . . Yes O52 C51 C5 109.3(7) . . Yes C51 O52 C52 120.3(6) . . Yes O52 C52 C54 109.3(5) . . Yes O52 C52 C55 108.7(5) . . Yes C54 C52 C55 114.5(7) . . Yes O52 C52 C53 100.8(6) . . Yes C54 C52 C53 110.5(6) . . Yes C55 C52 C53 112.1(7) . . Yes O71 C71 O72 122.5(7) . . Yes O71 C71 C7 126.8(6) . . Yes O72 C71 C7 110.7(7) . . Yes C71 O72 C72 114.6(6) . . Yes 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 C7A N1 C2 C3 -36.1(8) . . . . ? C N1 C2 C3 -159.2(6) . . . . ? N1 C2 C3 N4 38.8(7) . . . . ? N1 C2 C3 C31P 160.1(7) . . . . ? C31P C3 N4 C7A -152.0(6) . . . . ? C2 C3 N4 C7A -28.5(7) . . . . ? C31P C3 N4 C5 84.5(7) . . . . ? C2 C3 N4 C5 -151.9(5) . . . . ? C3 N4 C5 C51 -105.8(7) . . . . ? C7A N4 C5 C51 131.3(6) . . . . ? C3 N4 C5 C6 135.5(6) . . . . ? C7A N4 C5 C6 12.6(8) . . . . ? N4 C5 C6 C7 -32.5(8) . . . . ? C51 C5 C6 C7 -150.4(6) . . . . ? C5 C6 C7 C71 -78.7(7) . . . . ? C5 C6 C7 C7A 38.6(7) . . . . ? C2 N1 C7A N4 18.8(7) . . . . ? C N1 C7A N4 143.9(5) . . . . ? C2 N1 C7A C7 135.4(7) . . . . ? C N1 C7A C7 -99.5(7) . . . . ? C3 N4 C7A N1 6.9(7) . . . . ? C5 N4 C7A N1 133.8(6) . . . . ? C3 N4 C7A C7 -114.8(6) . . . . ? C5 N4 C7A C7 12.1(8) . . . . ? C71 C7 C7A N1 -28.2(9) . . . . ? C6 C7 C7A N1 -146.8(6) . . . . ? C71 C7 C7A N4 87.5(7) . . . . ? C6 C7 C7A N4 -31.2(8) . . . . ? C7A N1 C C11P 171.0(4) . . . . ? C2 N1 C C11P -68.1(6) . . . . ? N1 C C11P C16P -59.8(5) . . . . ? N1 C C11P C12P 123.0(3) . . . . ? C16P C11P C12P C13P 0.1(4) . . . . ? C C11P C12P C13P 177.3(2) . . . . ? C11P C12P C13P C14P 0.3(4) . . . . ? C12P C13P C14P C15P -0.9(8) . . . . ? C13P C14P C15P C16P 1.1(10) . . . . ? C12P C11P C16P C15P 0.1(8) . . . . ? C C11P C16P C15P -177.1(5) . . . . ? C14P C15P C16P C11P -0.7(10) . . . . ? N4 C3 C31P C32P -122.9(6) . . . . ? C2 C3 C31P C32P 121.6(6) . . . . ? N4 C3 C31P C36P 56.4(7) . . . . ? C2 C3 C31P C36P -59.1(9) . . . . ? C36P C31P C32P C33P 0.2(4) . . . . ? C3 C31P C32P C33P 179.5(5) . . . . ? C31P C32P C33P C34P 0.2(4) . . . . ? C32P C33P C34P C35P -0.3(8) . . . . ? C33P C34P C35P C36P 0.0(10) . . . . ? C32P C31P C36P C35P -0.5(8) . . . . ? C3 C31P C36P C35P -179.7(6) . . . . ? C34P C35P C36P C31P 0.4(9) . . . . ? N4 C5 C51 O51 -68.2(9) . . . . ? C6 C5 C51 O51 46.1(9) . . . . ? N4 C5 C51 O52 111.6(6) . . . . ? C6 C5 C51 O52 -134.1(6) . . . . ? O51 C51 O52 C52 -1.0(10) . . . . ? C5 C51 O52 C52 179.2(5) . . . . ? C51 O52 C52 C54 62.9(8) . . . . ? C51 O52 C52 C55 -62.7(8) . . . . ? C51 O52 C52 C53 179.2(6) . . . . ? C6 C7 C71 O71 33.0(10) . . . . ? C7A C7 C71 O71 -78.0(9) . . . . ? C6 C7 C71 O72 -147.3(6) . . . . ? C7A C7 C71 O72 101.7(6) . . . . ? O71 C71 O72 C72 -2.2(10) . . . . ? C7 C71 O72 C72 178.1(6) . . . . ? _refine_diff_density_max 0.30 _refine_diff_density_min -0.29 _refine_diff_density_rms 0.07 # Attachment '- Paper1_19.cif' data_jsphno _database_code_depnum_ccdc_archive 'CCDC 787236' #TrackingRef '- Paper1_19.cif' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C25 H28 N2 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C25 H28 N2 O4' _chemical_formula_weight 420.49 _chemical_melting_point ? _chemical_compound_source ? 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 11.351(2) _cell_length_b 9.7612(10) _cell_length_c 19.942(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.07(2) _cell_angle_gamma 90.00 _cell_volume 2209.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 58 _cell_measurement_theta_min 11 _cell_measurement_theta_max 13 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type nine _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3081 _diffrn_reflns_av_R_equivalents 0.0 _diffrn_reflns_av_sigmaI/netI 0.059 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 22.49 _reflns_number_total 3081 _reflns_number_observed 2091 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 9 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.056P)^2^+0.456P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0071(12) _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 'not reliably determined' _refine_ls_number_reflns 3072 _refine_ls_number_parameters 548 _refine_ls_number_restraints 33 _refine_ls_R_factor_all 0.0936 _refine_ls_R_factor_obs 0.0494 _refine_ls_wR_factor_all 0.141 _refine_ls_wR_factor_obs 0.100 _refine_ls_goodness_of_fit_all 1.006 _refine_ls_goodness_of_fit_obs 1.059 _refine_ls_restrained_S_all 1.169 _refine_ls_restrained_S_obs 1.049 _refine_ls_shift/esd_max 0.017 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N -0.0803(4) -0.4772(5) 0.1411(2) 0.0473(14) Uani 1 d . . C2 C 0.0264(5) -0.5582(7) 0.1471(4) 0.058(2) Uani 1 d . . H2A H 0.0201(5) -0.6409(7) 0.1203(4) 0.070 Uiso 1 calc R . H2B H 0.0422(5) -0.5834(7) 0.1934(4) 0.070 Uiso 1 calc R . C3 C 0.1230(5) -0.4643(7) 0.1208(3) 0.046(2) Uani 1 d . . H3A H 0.1235(5) -0.4695(7) 0.0718(3) 0.055 Uiso 1 calc R . N4 N 0.0819(4) -0.3279(5) 0.1409(2) 0.0422(13) Uani 1 d . . C5 C 0.0944(5) -0.2132(7) 0.0928(3) 0.052(2) Uani 1 d . . H5A H 0.0880(5) -0.2493(7) 0.0470(3) 0.062 Uiso 1 calc R . C6 C -0.0104(5) -0.1211(7) 0.1055(3) 0.058(2) Uani 1 d . . H6A H -0.0313(5) -0.0687(7) 0.0650(3) 0.069 Uiso 1 calc R . C7 C -0.1091(6) -0.2225(7) 0.1224(3) 0.057(2) Uani 1 d . . H7A H -0.1656(6) -0.1789(7) 0.1522(3) 0.069 Uiso 1 calc R . C7A C -0.0431(5) -0.3375(7) 0.1599(3) 0.047(2) Uani 1 d . . H7AA H -0.0501(5) -0.3248(7) 0.2084(3) 0.056 Uiso 1 calc R . C8 C 0.2171(7) -0.1517(8) 0.1037(4) 0.058(2) Uani 1 d . . O8 O 0.3040(4) -0.2042(6) 0.0817(3) 0.083(2) Uani 1 d . . O9 O 0.2275(4) -0.0393(6) 0.1415(3) 0.081(2) Uani 1 d . . C10 C 0.1281(7) 0.0484(9) 0.1524(4) 0.086(3) Uani 1 d . . H10A H 0.1174(7) 0.1073(9) 0.1136(4) 0.103 Uiso 1 calc R . H10B H 0.1455(7) 0.1066(9) 0.1908(4) 0.103 Uiso 1 calc R . C11 C 0.0178(6) -0.0245(8) 0.1641(4) 0.075(2) Uani 1 d . . H11A H -0.0458(6) 0.0410(8) 0.1690(4) 0.090 Uiso 1 calc R . H11B H 0.0247(6) -0.0768(8) 0.2054(4) 0.090 Uiso 1 calc R . C C -0.1735(3) -0.5282(5) 0.1846(2) 0.058(2) Uani 1 d . . H0A H -0.2397(3) -0.4654(5) 0.1829(2) 0.070 Uiso 1 calc R . H0B H -0.1440(3) -0.5316(5) 0.2306(2) 0.070 Uiso 1 calc R . C11P C -0.2146(3) -0.6690(5) 0.1636(2) 0.051(2) Uani 1 d RD . C12P C -0.2457(3) -0.7654(5) 0.2115(2) 0.059(2) Uani 1 d RD . H12A H -0.2351(3) -0.7447(5) 0.2567(2) 0.071 Uiso 1 calc R . C13P C -0.2918(6) -0.8906(8) 0.1934(4) 0.074(2) Uani 1 d D . H13A H -0.3115(6) -0.9536(8) 0.2264(4) 0.088 Uiso 1 calc R . C14P C -0.3088(6) -0.9232(9) 0.1271(4) 0.074(2) Uani 1 d D . H14A H -0.3421(6) -1.0066(9) 0.1146(4) 0.089 Uiso 1 calc R . C15P C -0.2756(7) -0.8299(9) 0.0794(4) 0.075(2) Uani 1 d D . H15A H -0.2842(7) -0.8516(9) 0.0341(4) 0.090 Uiso 1 calc R . C16P C -0.2299(6) -0.7052(8) 0.0978(4) 0.067(2) Uani 1 d D . H16A H -0.2087(6) -0.6435(8) 0.0646(4) 0.080 Uiso 1 calc R . C31P C 0.2414(5) -0.5097(7) 0.1484(3) 0.049(2) Uani 1 d D . C32P C 0.2940(5) -0.4514(8) 0.2034(3) 0.066(2) Uani 1 d D . H32A H 0.2618(5) -0.3721(8) 0.2214(3) 0.079 Uiso 1 calc R . C33P C 0.3944(6) -0.5077(8) 0.2332(3) 0.069(2) Uani 1 d D . H33A H 0.4289(6) -0.4657(8) 0.2705(3) 0.083 Uiso 1 calc R . C34P C 0.4426(6) -0.6243(9) 0.2079(4) 0.080(3) Uani 1 d D . H34A H 0.5098(6) -0.6624(9) 0.2277(4) 0.096 Uiso 1 calc R . C35P C 0.3910(7) -0.6837(10) 0.1534(5) 0.098(3) Uani 1 d D . H35A H 0.4232(7) -0.7628(10) 0.1353(5) 0.118 Uiso 1 calc R . C36P C 0.2912(6) -0.6271(9) 0.1248(4) 0.077(2) Uani 1 d D . H36A H 0.2562(6) -0.6705(9) 0.0880(4) 0.092 Uiso 1 calc R . C71 C -0.1722(6) -0.2775(8) 0.0609(4) 0.059(2) Uani 1 d . . O71 O -0.1282(4) -0.2882(7) 0.0068(3) 0.087(2) Uani 1 d . . O72 O -0.2822(4) -0.3105(5) 0.0744(2) 0.0674(14) Uani 1 d . . C72 C -0.3536(7) -0.3714(11) 0.0200(4) 0.092(3) Uani 1 d . . H72A H -0.3714(7) -0.3023(11) -0.0137(4) 0.110 Uiso 1 calc R . H72B H -0.3094(7) -0.4441(11) -0.0012(4) 0.110 Uiso 1 calc R . C73 C -0.4615(7) -0.4258(15) 0.0456(5) 0.142(5) Uani 1 d . . H73A H -0.5072(7) -0.4652(15) 0.0095(5) 0.213 Uiso 1 calc R . H73B H -0.5056(7) -0.3535(15) 0.0660(5) 0.213 Uiso 1 calc R . H73C H -0.4438(7) -0.4950(15) 0.0784(5) 0.213 Uiso 1 calc R . N1' N -0.2463(4) -0.0166(5) 0.4315(2) 0.0486(14) Uani 1 d . . C2' C -0.1489(5) 0.0178(7) 0.3871(3) 0.058(2) Uani 1 d . . H2'A H -0.1778(5) 0.0553(7) 0.3449(3) 0.070 Uiso 1 calc R . H2'B H -0.1003(5) -0.0617(7) 0.3783(3) 0.070 Uiso 1 calc R . C3' C -0.0814(5) 0.1246(7) 0.4278(3) 0.046(2) Uani 1 d . . H3'A H -0.1258(5) 0.2107(7) 0.4263(3) 0.056 Uiso 1 calc R . N4' N -0.0866(4) 0.0687(6) 0.4959(3) 0.0509(14) Uani 1 d . . C5' C -0.0907(5) 0.1679(8) 0.5494(3) 0.059(2) Uani 1 d . . H5'A H -0.0583(5) 0.2543(8) 0.5328(3) 0.071 Uiso 1 calc R . C6' C -0.2213(5) 0.1908(8) 0.5639(3) 0.056(2) Uani 1 d . . H6'A H -0.2559(5) 0.2497(8) 0.5290(3) 0.067 Uiso 1 calc R . C7' C -0.2699(5) 0.0438(7) 0.5552(3) 0.053(2) Uani 1 d . . H7'A H -0.2551(5) -0.0065(7) 0.5970(3) 0.063 Uiso 1 calc R . C7A' C -0.1934(5) -0.0202(7) 0.4998(3) 0.051(2) Uani 1 d . . H7AB H -0.1709(5) -0.1141(7) 0.5119(3) 0.062 Uiso 1 calc R . C8' C -0.0199(8) 0.1263(11) 0.6118(5) 0.082(3) Uani 1 d . . O8' O 0.0548(6) 0.0396(8) 0.6126(3) 0.113(2) Uani 1 d . . O9' O -0.0466(7) 0.1936(9) 0.6687(3) 0.112(2) Uani 1 d . . C10' C -0.1370(10) 0.3001(13) 0.6659(5) 0.116(4) Uani 1 d . . H10C H -0.1068(10) 0.3789(13) 0.6421(5) 0.139 Uiso 1 calc R . H10D H -0.1548(10) 0.3289(13) 0.7112(5) 0.139 Uiso 1 calc R . C11' C -0.2458(8) 0.2525(10) 0.6323(4) 0.090(3) Uani 1 d . . H11C H -0.2997(8) 0.3290(10) 0.6268(4) 0.108 Uiso 1 calc R . H11D H -0.2834(8) 0.1844(10) 0.6601(4) 0.108 Uiso 1 calc R . C' C -0.3039(3) -0.1469(5) 0.4144(2) 0.064(2) Uani 1 d . . H'A H -0.3576(3) -0.1712(5) 0.4497(2) 0.077 Uiso 1 calc R . H'B H -0.2446(3) -0.2182(5) 0.4121(2) 0.077 Uiso 1 calc R . C1B' C -0.3709(3) -0.1416(5) 0.3491(2) 0.056(2) Uani 1 d RD . C12' C -0.4646(3) -0.0517(5) 0.3393(2) 0.066(2) Uani 1 d RD . H12B H -0.4841(3) 0.0100(5) 0.3729(2) 0.079 Uiso 1 calc R . C13' C -0.5290(6) -0.0540(9) 0.2796(4) 0.075(2) Uani 1 d D . H13B H -0.5920(6) 0.0059(9) 0.2738(4) 0.090 Uiso 1 calc R . C14' C -0.5020(7) -0.1421(9) 0.2293(4) 0.070(2) Uani 1 d D . H14B H -0.5465(7) -0.1432(9) 0.1896(4) 0.085 Uiso 1 calc R . C15' C -0.4090(7) -0.2287(9) 0.2378(4) 0.079(2) Uani 1 d D . H15B H -0.3890(7) -0.2887(9) 0.2036(4) 0.095 Uiso 1 calc R . C16' C -0.3443(6) -0.2276(8) 0.2971(4) 0.075(2) Uani 1 d D . H16B H -0.2807(6) -0.2870(8) 0.3020(4) 0.090 Uiso 1 calc R . C31' C 0.0413(5) 0.1519(7) 0.4044(3) 0.048(2) Uani 1 d D . C32' C 0.0591(6) 0.2261(8) 0.3468(4) 0.063(2) Uani 1 d D . H32B H -0.0062(6) 0.2592(8) 0.3230(4) 0.075 Uiso 1 calc R . C33' C 0.1702(6) 0.2531(8) 0.3229(4) 0.068(2) Uani 1 d D . H33B H 0.1793(6) 0.3022(8) 0.2834(4) 0.082 Uiso 1 calc R . C34' C 0.2669(6) 0.2063(8) 0.3584(4) 0.066(2) Uani 1 d D . H34B H 0.3421(6) 0.2236(8) 0.3427(4) 0.079 Uiso 1 calc R . C35' C 0.2533(6) 0.1339(8) 0.4171(4) 0.065(2) Uani 1 d D . H35B H 0.3189(6) 0.1037(8) 0.4415(4) 0.078 Uiso 1 calc R . C36' C 0.1407(5) 0.1066(7) 0.4397(3) 0.060(2) Uani 1 d D . H36B H 0.1316(5) 0.0571(7) 0.4791(3) 0.071 Uiso 1 calc R . C71' C -0.4007(6) 0.0466(9) 0.5416(3) 0.057(2) Uani 1 d . . O71' O -0.4520(4) 0.1278(7) 0.5083(3) 0.093(2) Uani 1 d . . O72' O -0.4546(4) -0.0547(6) 0.5724(2) 0.0741(15) Uani 1 d . . C72' C -0.5836(6) -0.0591(11) 0.5661(4) 0.094(3) Uani 1 d . . H72C H -0.6141(6) 0.0337(11) 0.5634(4) 0.112 Uiso 1 calc R . H72D H -0.6059(6) -0.1061(11) 0.5249(4) 0.112 Uiso 1 calc R . C73' C -0.6333(7) -0.1258(14) 0.6201(5) 0.128(4) Uani 1 d . . H73D H -0.7175(7) -0.1271(14) 0.6145(5) 0.192 Uiso 1 calc R . H73E H -0.6125(7) -0.0785(14) 0.6608(5) 0.192 Uiso 1 calc R . H73F H -0.6043(7) -0.2181(14) 0.6224(5) 0.192 Uiso 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 0.040(3) 0.050(4) 0.052(3) 0.000(3) 0.005(2) -0.002(3) C2 0.051(4) 0.045(4) 0.079(5) 0.003(4) -0.001(4) 0.003(4) C3 0.042(4) 0.046(4) 0.051(4) 0.000(4) -0.002(3) 0.007(3) N4 0.043(3) 0.037(3) 0.047(3) 0.003(3) 0.002(2) 0.001(3) C5 0.059(4) 0.052(5) 0.045(4) -0.002(4) -0.009(3) -0.010(4) C6 0.056(4) 0.053(5) 0.063(4) 0.003(4) -0.016(3) 0.015(4) C7 0.053(4) 0.060(5) 0.058(4) -0.010(4) -0.016(3) 0.010(4) C7A 0.050(4) 0.039(4) 0.050(4) -0.003(4) 0.000(3) 0.004(3) C8 0.061(5) 0.058(5) 0.055(5) 0.010(4) -0.008(4) -0.012(4) O8 0.054(3) 0.095(5) 0.099(4) -0.013(4) 0.010(3) 0.001(3) O9 0.065(3) 0.061(4) 0.116(4) -0.026(4) -0.013(3) -0.007(3) C10 0.082(6) 0.058(5) 0.119(7) -0.029(5) 0.000(5) 0.004(5) C11 0.073(5) 0.054(5) 0.099(6) -0.018(5) 0.002(4) -0.009(5) C 0.061(4) 0.053(5) 0.060(4) -0.002(4) 0.006(3) 0.003(4) C11P 0.041(4) 0.051(5) 0.060(5) 0.003(4) 0.003(3) 0.001(3) C12P 0.051(4) 0.066(6) 0.061(4) 0.009(5) 0.002(3) -0.001(4) C13P 0.058(5) 0.069(6) 0.095(6) 0.021(5) 0.009(4) -0.010(5) C14P 0.061(5) 0.056(6) 0.106(7) 0.011(6) -0.002(5) -0.009(4) C15P 0.078(5) 0.072(6) 0.074(6) -0.011(5) -0.007(4) -0.011(5) C16P 0.073(5) 0.058(5) 0.069(6) 0.015(5) 0.005(4) -0.006(4) C31P 0.038(4) 0.042(4) 0.067(4) -0.009(4) 0.002(3) -0.002(3) C32P 0.059(4) 0.061(5) 0.078(5) -0.014(5) -0.013(4) 0.015(4) C33P 0.059(5) 0.078(6) 0.069(5) 0.000(5) -0.021(4) 0.007(4) C34P 0.046(4) 0.084(7) 0.110(7) -0.011(6) -0.012(4) 0.024(5) C35P 0.069(5) 0.088(7) 0.137(8) -0.044(7) -0.023(5) 0.027(5) C36P 0.063(5) 0.082(6) 0.086(6) -0.039(5) -0.024(4) 0.015(5) C71 0.050(4) 0.062(5) 0.063(5) 0.010(5) -0.009(4) 0.002(4) O71 0.067(3) 0.136(6) 0.056(3) 0.012(4) -0.008(3) -0.016(4) O72 0.046(3) 0.083(4) 0.073(3) -0.002(3) -0.012(2) -0.006(3) C72 0.079(5) 0.121(8) 0.074(5) 0.010(6) -0.022(4) -0.035(6) C73 0.064(6) 0.214(14) 0.148(9) -0.029(10) -0.014(6) -0.040(8) N1' 0.043(3) 0.046(4) 0.056(3) 0.000(3) -0.003(3) 0.000(3) C2' 0.049(4) 0.061(5) 0.064(4) -0.002(4) -0.006(3) -0.003(4) C3' 0.039(4) 0.050(4) 0.050(4) 0.003(4) -0.004(3) -0.002(3) N4' 0.042(3) 0.055(4) 0.055(3) 0.011(3) -0.006(2) -0.004(3) C5' 0.060(4) 0.061(5) 0.056(4) 0.021(4) -0.010(3) -0.022(4) C6' 0.060(5) 0.062(5) 0.045(4) -0.006(4) -0.002(3) -0.006(4) C7' 0.044(4) 0.060(5) 0.054(4) 0.013(4) -0.003(3) -0.006(4) C7A' 0.042(4) 0.048(4) 0.064(4) 0.019(4) -0.004(3) -0.005(3) C8' 0.079(6) 0.094(8) 0.070(6) 0.028(6) -0.027(5) -0.035(6) O8' 0.098(5) 0.119(6) 0.121(5) 0.040(5) -0.054(4) -0.006(4) O9' 0.138(6) 0.144(7) 0.053(4) 0.011(5) -0.033(4) -0.041(5) C10' 0.134(9) 0.143(11) 0.072(7) -0.015(7) 0.013(6) -0.048(9) C11' 0.098(6) 0.097(7) 0.073(6) -0.009(5) 0.011(5) -0.032(6) C' 0.063(4) 0.045(5) 0.082(5) -0.005(4) -0.011(4) -0.006(4) C1B' 0.046(4) 0.059(5) 0.063(5) -0.011(4) 0.003(4) -0.018(4) C12' 0.052(4) 0.078(6) 0.069(5) -0.020(5) 0.003(4) 0.005(4) C13' 0.051(4) 0.092(7) 0.083(5) -0.002(6) -0.008(4) -0.003(5) C14' 0.061(5) 0.084(6) 0.067(5) -0.011(5) 0.000(4) -0.017(5) C15' 0.080(6) 0.079(6) 0.078(6) -0.017(5) 0.006(5) -0.021(5) C16' 0.062(5) 0.071(6) 0.092(6) -0.023(5) -0.002(4) -0.008(4) C31' 0.043(4) 0.048(4) 0.054(4) -0.004(4) 0.001(3) 0.007(3) C32' 0.050(4) 0.077(6) 0.061(5) 0.016(5) 0.000(4) -0.001(4) C33' 0.070(5) 0.069(6) 0.066(5) -0.001(4) 0.007(4) -0.007(4) C34' 0.050(4) 0.068(5) 0.080(5) -0.020(5) 0.015(4) -0.008(4) C35' 0.047(4) 0.071(6) 0.078(5) 0.005(5) 0.003(4) 0.002(4) C36' 0.051(4) 0.060(5) 0.067(5) -0.004(4) -0.007(4) 0.003(4) C71' 0.056(5) 0.062(5) 0.054(4) 0.006(4) 0.000(4) -0.006(4) O71' 0.060(3) 0.115(5) 0.105(4) 0.049(4) -0.004(3) 0.011(3) O72' 0.051(3) 0.081(4) 0.090(4) 0.010(3) -0.013(2) -0.011(3) C72' 0.043(4) 0.129(8) 0.108(7) 0.025(7) -0.014(4) -0.034(5) C73' 0.066(6) 0.199(13) 0.119(8) 0.008(9) 0.002(5) -0.038(8) _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 C2 1.450(8) . ? N1 C 1.467(6) . ? N1 C7A 1.473(8) . ? C2 C3 1.529(9) . ? C3 N4 1.469(8) . ? C3 C31P 1.508(8) . ? N4 C7A 1.477(7) . ? N4 C5 1.484(8) . ? C5 C6 1.516(9) . ? C5 C8 1.529(9) . ? C6 C11 1.532(9) . ? C6 C7 1.537(9) . ? C7 C71 1.506(9) . ? C7 C7A 1.536(9) . ? C8 O8 1.202(8) . ? C8 O9 1.335(9) . ? O9 C10 1.436(8) . ? C10 C11 1.463(10) . ? C C11P 1.51 . ? C11P C16P 1.368(8) . ? C11P C12P 1.39 . ? C12P C13P 1.375(9) . ? C13P C14P 1.371(9) . ? C14P C15P 1.374(10) . ? C15P C16P 1.370(9) . ? C31P C32P 1.364(8) . ? C31P C36P 1.365(9) . ? C32P C33P 1.389(8) . ? C33P C34P 1.364(9) . ? C34P C35P 1.356(10) . ? C35P C36P 1.375(9) . ? C71 O71 1.203(7) . ? C71 O72 1.322(8) . ? O72 C72 1.468(8) . ? C72 C73 1.438(10) . ? N1' C' 1.468(6) . ? N1' C2' 1.468(7) . ? N1' C7A' 1.478(7) . ? C2' C3' 1.519(8) . ? C3' N4' 1.466(7) . ? C3' C31' 1.501(8) . ? N4' C5' 1.444(8) . ? N4' C7A' 1.494(7) . ? C5' C8' 1.523(10) . ? C5' C6' 1.532(9) . ? C6' C11' 1.521(10) . ? C6' C7' 1.545(9) . ? C7' C71' 1.505(8) . ? C7' C7A' 1.550(9) . ? C8' O8' 1.198(11) . ? C8' O9' 1.352(11) . ? O9' C10' 1.461(12) . ? C10' C11' 1.470(11) . ? C' C1B' 1.50 . ? C1B' C16' 1.371(8) . ? C1B' C12' 1.39 . ? C12' C13' 1.385(7) . ? C13' C14' 1.361(9) . ? C14' C15' 1.360(9) . ? C15' C16' 1.381(9) . ? C31' C32' 1.376(8) . ? C31' C36' 1.391(8) . ? C32' C33' 1.381(8) . ? C33' C34' 1.373(9) . ? C34' C35' 1.380(9) . ? C35' C36' 1.388(8) . ? C71' O71' 1.180(8) . ? C71' O72' 1.321(8) . ? O72' C72' 1.468(7) . ? C72' C73' 1.389(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 C2 N1 C 112.1(5) . . ? C2 N1 C7A 104.4(5) . . ? C N1 C7A 111.8(5) . . ? N1 C2 C3 104.4(5) . . ? N4 C3 C31P 116.9(5) . . ? N4 C3 C2 102.5(5) . . ? C31P C3 C2 109.8(5) . . ? C3 N4 C7A 108.9(5) . . ? C3 N4 C5 118.2(5) . . ? C7A N4 C5 108.5(5) . . ? N4 C5 C6 104.7(5) . . ? N4 C5 C8 107.6(5) . . ? C6 C5 C8 117.3(6) . . ? C5 C6 C11 109.8(5) . . ? C5 C6 C7 103.4(5) . . ? C11 C6 C7 111.8(6) . . ? C71 C7 C7A 110.8(6) . . ? C71 C7 C6 112.9(6) . . ? C7A C7 C6 103.1(5) . . ? N1 C7A N4 105.4(5) . . ? N1 C7A C7 114.7(5) . . ? N4 C7A C7 106.9(5) . . ? O8 C8 O9 119.5(7) . . ? O8 C8 C5 122.2(7) . . ? O9 C8 C5 118.3(7) . . ? C8 O9 C10 121.0(6) . . ? O9 C10 C11 114.3(7) . . ? C10 C11 C6 110.1(6) . . ? N1 C C11P 111.6(3) . . ? C16P C11P C12P 117.0(4) . . ? C16P C11P C 122.3(4) . . ? C12P C11P C 120.5 . . ? C13P C12P C11P 121.5(4) . . ? C14P C13P C12P 120.3(7) . . ? C13P C14P C15P 118.6(8) . . ? C16P C15P C14P 120.7(7) . . ? C11P C16P C15P 121.8(7) . . ? C32P C31P C36P 116.7(6) . . ? C32P C31P C3 122.9(6) . . ? C36P C31P C3 119.6(6) . . ? C31P C32P C33P 121.5(7) . . ? C34P C33P C32P 120.3(7) . . ? C35P C34P C33P 118.9(7) . . ? C34P C35P C36P 120.0(8) . . ? C31P C36P C35P 122.6(7) . . ? O71 C71 O72 124.7(6) . . ? O71 C71 C7 124.3(7) . . ? O72 C71 C7 111.0(6) . . ? C71 O72 C72 117.4(6) . . ? C73 C72 O72 110.4(6) . . ? C' N1' C2' 113.3(4) . . ? C' N1' C7A' 111.5(4) . . ? C2' N1' C7A' 105.3(4) . . ? N1' C2' C3' 102.3(5) . . ? N4' C3' C31' 114.0(5) . . ? N4' C3' C2' 102.1(5) . . ? C31' C3' C2' 114.7(5) . . ? C5' N4' C3' 116.0(5) . . ? C5' N4' C7A' 108.3(5) . . ? C3' N4' C7A' 108.1(4) . . ? N4' C5' C8' 113.6(7) . . ? N4' C5' C6' 106.4(5) . . ? C8' C5' C6' 112.5(6) . . ? C11' C6' C5' 114.9(6) . . ? C11' C6' C7' 113.5(6) . . ? C5' C6' C7' 100.8(6) . . ? C71' C7' C6' 110.6(6) . . ? C71' C7' C7A' 116.3(5) . . ? C6' C7' C7A' 104.6(5) . . ? N1' C7A' N4' 104.7(5) . . ? N1' C7A' C7' 115.1(5) . . ? N4' C7A' C7' 105.6(5) . . ? O8' C8' O9' 120.1(9) . . ? O8' C8' C5' 124.2(10) . . ? O9' C8' C5' 115.7(9) . . ? C8' O9' C10' 118.8(7) . . ? O9' C10' C11' 112.1(9) . . ? C10' C11' C6' 111.6(7) . . ? N1' C' C1B' 112.9(2) . . ? C16' C1B' C12' 117.3(4) . . ? C16' C1B' C' 121.4(4) . . ? C12' C1B' C' 121.2 . . ? C13' C12' C1B' 120.0(4) . . ? C14' C13' C12' 121.5(7) . . ? C15' C14' C13' 119.0(7) . . ? C14' C15' C16' 120.1(8) . . ? C1B' C16' C15' 122.1(7) . . ? C32' C31' C36' 117.3(6) . . ? C32' C31' C3' 120.3(5) . . ? C36' C31' C3' 122.3(6) . . ? C31' C32' C33' 122.5(6) . . ? C34' C33' C32' 119.0(7) . . ? C33' C34' C35' 120.4(7) . . ? C34' C35' C36' 119.5(6) . . ? C35' C36' C31' 121.2(7) . . ? O71' C71' O72' 122.5(6) . . ? O71' C71' C7' 126.0(7) . . ? O72' C71' C7' 111.5(6) . . ? C71' O72' C72' 116.8(6) . . ? C73' C72' O72' 111.4(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C N1 C2 C3 -159.7(5) . . . . ? C7A N1 C2 C3 -38.5(6) . . . . ? N1 C2 C3 N4 32.7(6) . . . . ? N1 C2 C3 C31P 157.7(5) . . . . ? C31P C3 N4 C7A -134.8(5) . . . . ? C2 C3 N4 C7A -14.7(6) . . . . ? C31P C3 N4 C5 100.9(6) . . . . ? C2 C3 N4 C5 -139.0(5) . . . . ? C3 N4 C5 C6 147.3(5) . . . . ? C7A N4 C5 C6 22.8(6) . . . . ? C3 N4 C5 C8 -87.2(7) . . . . ? C7A N4 C5 C8 148.3(6) . . . . ? N4 C5 C6 C11 84.0(6) . . . . ? C8 C5 C6 C11 -35.2(8) . . . . ? N4 C5 C6 C7 -35.5(6) . . . . ? C8 C5 C6 C7 -154.7(5) . . . . ? C5 C6 C7 C71 -85.2(6) . . . . ? C11 C6 C7 C71 156.7(6) . . . . ? C5 C6 C7 C7A 34.4(6) . . . . ? C11 C6 C7 C7A -83.7(6) . . . . ? C2 N1 C7A N4 29.2(6) . . . . ? C N1 C7A N4 150.6(4) . . . . ? C2 N1 C7A C7 146.5(5) . . . . ? C N1 C7A C7 -92.1(6) . . . . ? C3 N4 C7A N1 -8.2(6) . . . . ? C5 N4 C7A N1 121.7(5) . . . . ? C3 N4 C7A C7 -130.7(5) . . . . ? C5 N4 C7A C7 -0.8(6) . . . . ? C71 C7 C7A N1 -16.5(8) . . . . ? C6 C7 C7A N1 -137.5(6) . . . . ? C71 C7 C7A N4 100.0(6) . . . . ? C6 C7 C7A N4 -21.0(6) . . . . ? N4 C5 C8 O8 78.8(8) . . . . ? C6 C5 C8 O8 -163.6(7) . . . . ? N4 C5 C8 O9 -98.3(7) . . . . ? C6 C5 C8 O9 19.4(9) . . . . ? O8 C8 O9 C10 161.7(7) . . . . ? C5 C8 O9 C10 -21.2(9) . . . . ? C8 O9 C10 C11 41.2(10) . . . . ? O9 C10 C11 C6 -56.6(9) . . . . ? C5 C6 C11 C10 53.0(8) . . . . ? C7 C6 C11 C10 167.2(6) . . . . ? C2 N1 C C11P -65.4(5) . . . . ? C7A N1 C C11P 177.8(3) . . . . ? N1 C C11P C16P -40.5(4) . . . . ? N1 C C11P C12P 143.4(2) . . . . ? C16P C11P C12P C13P -1.2(5) . . . . ? C C11P C12P C13P 175.1(4) . . . . ? C11P C12P C13P C14P -0.3(8) . . . . ? C12P C13P C14P C15P 1.9(10) . . . . ? C13P C14P C15P C16P -2.0(11) . . . . ? C12P C11P C16P C15P 1.1(8) . . . . ? C C11P C16P C15P -175.1(5) . . . . ? C14P C15P C16P C11P 0.5(11) . . . . ? N4 C3 C31P C32P 19.1(9) . . . . ? C2 C3 C31P C32P -97.0(7) . . . . ? N4 C3 C31P C36P -171.5(6) . . . . ? C2 C3 C31P C36P 72.3(8) . . . . ? C36P C31P C32P C33P 1.0(10) . . . . ? C3 C31P C32P C33P 170.7(7) . . . . ? C31P C32P C33P C34P -0.4(11) . . . . ? C32P C33P C34P C35P 0.1(12) . . . . ? C33P C34P C35P C36P -0.5(14) . . . . ? C32P C31P C36P C35P -1.5(11) . . . . ? C3 C31P C36P C35P -171.5(8) . . . . ? C34P C35P C36P C31P 1.3(14) . . . . ? C7A C7 C71 O71 -87.5(9) . . . . ? C6 C7 C71 O71 27.5(10) . . . . ? C7A C7 C71 O72 93.3(7) . . . . ? C6 C7 C71 O72 -151.7(6) . . . . ? O71 C71 O72 C72 3.4(12) . . . . ? C7 C71 O72 C72 -177.4(6) . . . . ? C71 O72 C72 C73 168.6(8) . . . . ? C' N1' C2' C3' -161.9(4) . . . . ? C7A' N1' C2' C3' -39.9(6) . . . . ? N1' C2' C3' N4' 40.0(6) . . . . ? N1' C2' C3' C31' 163.8(5) . . . . ? C31' C3' N4' C5' 88.3(6) . . . . ? C2' C3' N4' C5' -147.4(5) . . . . ? C31' C3' N4' C7A' -150.0(5) . . . . ? C2' C3' N4' C7A' -25.6(6) . . . . ? C3' N4' C5' C8' -142.2(6) . . . . ? C7A' N4' C5' C8' 96.1(6) . . . . ? C3' N4' C5' C6' 93.5(6) . . . . ? C7A' N4' C5' C6' -28.2(6) . . . . ? N4' C5' C6' C11' 160.3(6) . . . . ? C8' C5' C6' C11' 35.3(10) . . . . ? N4' C5' C6' C7' 37.9(6) . . . . ? C8' C5' C6' C7' -87.1(7) . . . . ? C11' C6' C7' C71' 77.7(7) . . . . ? C5' C6' C7' C71' -158.9(5) . . . . ? C11' C6' C7' C7A' -156.3(6) . . . . ? C5' C6' C7' C7A' -32.9(6) . . . . ? C' N1' C7A' N4' 147.2(5) . . . . ? C2' N1' C7A' N4' 24.0(6) . . . . ? C' N1' C7A' C7' -97.3(6) . . . . ? C2' N1' C7A' C7' 139.5(6) . . . . ? C5' N4' C7A' N1' 128.2(5) . . . . ? C3' N4' C7A' N1' 1.8(7) . . . . ? C5' N4' C7A' C7' 6.3(6) . . . . ? C3' N4' C7A' C7' -120.1(5) . . . . ? C71' C7' C7A' N1' 24.9(9) . . . . ? C6' C7' C7A' N1' -97.4(6) . . . . ? C71' C7' C7A' N4' 139.8(6) . . . . ? C6' C7' C7A' N4' 17.5(6) . . . . ? N4' C5' C8' O8' 17.5(11) . . . . ? C6' C5' C8' O8' 138.5(9) . . . . ? N4' C5' C8' O9' -162.1(6) . . . . ? C6' C5' C8' O9' -41.1(9) . . . . ? O8' C8' O9' C10' 179.2(8) . . . . ? C5' C8' O9' C10' -1.2(11) . . . . ? C8' O9' C10' C11' 50.2(11) . . . . ? O9' C10' C11' C6' -52.4(11) . . . . ? C5' C6' C11' C10' 10.1(11) . . . . ? C7' C6' C11' C10' 125.3(8) . . . . ? C2' N1' C' C1B' -68.4(4) . . . . ? C7A' N1' C' C1B' 173.1(3) . . . . ? N1' C' C1B' C16' 120.6(5) . . . . ? N1' C' C1B' C12' -61.2(3) . . . . ? C16' C1B' C12' C13' 1.7(5) . . . . ? C' C1B' C12' C13' -176.6(4) . . . . ? C1B' C12' C13' C14' -0.6(9) . . . . ? C12' C13' C14' C15' -0.6(11) . . . . ? C13' C14' C15' C16' 0.8(12) . . . . ? C12' C1B' C16' C15' -1.7(8) . . . . ? C' C1B' C16' C15' 176.7(5) . . . . ? C14' C15' C16' C1B' 0.4(11) . . . . ? N4' C3' C31' C32' -168.6(6) . . . . ? C2' C3' C31' C32' 74.1(8) . . . . ? N4' C3' C31' C36' 10.3(9) . . . . ? C2' C3' C31' C36' -107.0(7) . . . . ? C36' C31' C32' C33' 1.5(10) . . . . ? C3' C31' C32' C33' -179.5(7) . . . . ? C31' C32' C33' C34' -1.1(11) . . . . ? C32' C33' C34' C35' -0.3(11) . . . . ? C33' C34' C35' C36' 1.0(11) . . . . ? C34' C35' C36' C31' -0.6(11) . . . . ? C32' C31' C36' C35' -0.7(10) . . . . ? C3' C31' C36' C35' -179.6(7) . . . . ? C6' C7' C71' O71' 38.1(10) . . . . ? C7A' C7' C71' O71' -81.0(10) . . . . ? C6' C7' C71' O72' -141.4(6) . . . . ? C7A' C7' C71' O72' 99.5(7) . . . . ? O71' C71' O72' C72' -2.7(11) . . . . ? C7' C71' O72' C72' 176.9(6) . . . . ? C71' O72' C72' C73' -154.0(8) . . . . ? _refine_diff_density_max 0.157 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.034