Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Thorfinnur Gunnlaugsson' 'Mark Nieuwenhuyzen' 'Ludovic Richard' 'Vera Thoss' _publ_contact_author_name 'Dr Thorfinnur Gunnlaugsson' _publ_contact_author_address ; Dr Thorfinnur Gunnlaugsson Department of Chemistry Trinity College Dublin Dublin 2 REPUBLIC OF IRELAND ; _publ_contact_author_email 'GUNNLAUT@TCD.IE' data_thorrnam _database_code_CSD 166865 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 F6 N4 O7 P' _chemical_formula_weight 620.49 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.543(4) _cell_length_b 25.740(12) _cell_length_c 14.221(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.167(12) _cell_angle_gamma 90.00 _cell_volume 2699(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1030 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 21 _exptl_crystal_description Plate _exptl_crystal_colour 'Pale Orange' _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 0.194 _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 153(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 8768 _diffrn_reflns_av_R_equivalents 0.0927 _diffrn_reflns_av_sigmaI/netI 0.1583 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4523 _reflns_number_gt 2066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1051P)^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 4523 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1528 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.2227 _refine_ls_wR_factor_gt 0.1561 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _refine_ls_shift/su_max 0.004 _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 P1 P 0.6357(2) 0.60757(7) 0.72266(12) 0.0335(5) Uani 1 1 d . . . F11 F 0.8319(5) 0.59423(16) 0.7049(3) 0.0541(12) Uani 1 1 d . . . F12 F 0.4410(6) 0.6207(2) 0.7408(3) 0.0732(15) Uani 1 1 d . . . F13 F 0.6663(6) 0.66691(15) 0.6994(3) 0.0630(13) Uani 1 1 d . . . F14 F 0.7228(5) 0.61783(14) 0.8338(3) 0.0447(10) Uani 1 1 d . . . F15 F 0.6092(7) 0.54802(15) 0.7461(3) 0.0638(14) Uani 1 1 d . . . F16 F 0.5506(5) 0.59811(15) 0.6122(2) 0.0476(11) Uani 1 1 d . . . O1 O 0.4331(6) 0.44186(18) 0.7700(3) 0.0430(13) Uani 1 1 d . . . O2 O 0.2281(7) 0.49228(18) 0.6842(3) 0.0449(13) Uani 1 1 d . . . N3 N 0.3124(8) 0.4747(2) 0.7619(4) 0.0373(14) Uani 1 1 d . . . C4 C 0.2647(8) 0.4942(2) 0.8490(4) 0.0264(14) Uani 1 1 d . . . C5 C 0.3178(8) 0.4648(2) 0.9335(4) 0.0268(15) Uani 1 1 d . . . H5A H 0.3810 0.4329 0.9335 0.032 Uiso 1 1 calc R . . C6 C 0.2746(8) 0.4840(2) 1.0165(5) 0.0312(15) Uani 1 1 d . . . H6A H 0.3034 0.4644 1.0743 0.037 Uiso 1 1 calc R . . C7 C 0.1895(8) 0.5318(2) 1.0161(4) 0.0276(15) Uani 1 1 d . . . C8 C 0.1363(8) 0.5605(2) 0.9327(5) 0.0320(16) Uani 1 1 d . . . H8A H 0.0768 0.5929 0.9337 0.038 Uiso 1 1 calc R . . C9 C 0.1717(8) 0.5408(2) 0.8463(4) 0.0288(15) Uani 1 1 d . . . H9A H 0.1327 0.5590 0.7874 0.035 Uiso 1 1 calc R . . N10 N 0.1619(7) 0.54893(19) 1.1078(3) 0.0265(12) Uani 1 1 d . . . N11 N 0.1307(7) 0.59655(19) 1.1126(3) 0.0272(12) Uani 1 1 d . . . C12 C 0.1051(8) 0.6124(2) 1.2063(5) 0.0305(15) Uani 1 1 d . . . C13 C 0.0474(8) 0.6625(2) 1.2146(5) 0.0301(15) Uani 1 1 d . . . H13A H 0.0288 0.6849 1.1603 0.036 Uiso 1 1 calc R . . C14 C 0.0163(8) 0.6804(2) 1.3006(4) 0.0260(14) Uani 1 1 d . . . H14A H -0.0283 0.7146 1.3057 0.031 Uiso 1 1 calc R . . C15 C 0.0515(8) 0.6476(2) 1.3800(4) 0.0264(15) Uani 1 1 d . . . C16 C 0.1173(8) 0.5972(2) 1.3733(4) 0.0266(14) Uani 1 1 d . . . C17 C 0.1407(8) 0.5790(2) 1.2840(4) 0.0255(14) Uani 1 1 d . . . H17A H 0.1803 0.5445 1.2770 0.031 Uiso 1 1 calc R . . O18 O 0.1492(6) 0.56865(15) 1.4541(3) 0.0338(11) Uani 1 1 d . . . C19 C 0.2273(10) 0.5179(2) 1.4503(5) 0.0452(19) Uani 1 1 d . . . H19A H 0.2630 0.5039 1.5156 0.068 Uiso 1 1 calc R . . H19B H 0.3344 0.5205 1.4217 0.068 Uiso 1 1 calc R . . H19C H 0.1379 0.4949 1.4111 0.068 Uiso 1 1 calc R . . N20 N 0.0061(7) 0.66773(19) 1.4680(3) 0.0267(12) Uani 1 1 d . . . H20 H -0.056(7) 0.706(2) 1.445(4) 0.020(14) Uiso 1 1 d . . . C21 C 0.1700(8) 0.6749(2) 1.5506(4) 0.0303(15) Uani 1 1 d . . . H21A H 0.1310 0.6923 1.6049 0.036 Uiso 1 1 calc R . . H21B H 0.2194 0.6404 1.5731 0.036 Uiso 1 1 calc R . . C22 C 0.3167(8) 0.7067(2) 1.5209(4) 0.0314(15) Uani 1 1 d . . . H22A H 0.4044 0.7183 1.5791 0.038 Uiso 1 1 calc R . . H22B H 0.3828 0.6848 1.4825 0.038 Uiso 1 1 calc R . . O23 O 0.2445(6) 0.75084(17) 1.4658(3) 0.0389(12) Uani 1 1 d . . . C24 C 0.1919(9) 0.7925(3) 1.5206(5) 0.0418(18) Uani 1 1 d . . . H24A H 0.2819 0.8210 1.5273 0.050 Uiso 1 1 calc R . . H24B H 0.1851 0.7802 1.5857 0.050 Uiso 1 1 calc R . . C25 C 0.0088(10) 0.8116(2) 1.4682(5) 0.0433(18) Uani 1 1 d . . . H25A H -0.0258 0.8428 1.5011 0.052 Uiso 1 1 calc R . . H25B H 0.0146 0.8215 1.4017 0.052 Uiso 1 1 calc R . . O26 O -0.1229(6) 0.77221(15) 1.4660(3) 0.0296(10) Uani 1 1 d . . . C27 C -0.3033(8) 0.7908(2) 1.4405(4) 0.0330(16) Uani 1 1 d . . . H27A H -0.3159 0.8211 1.4814 0.040 Uiso 1 1 calc R . . H27B H -0.3861 0.7633 1.4543 0.040 Uiso 1 1 calc R . . C28 C -0.3625(9) 0.8067(2) 1.3351(4) 0.0345(16) Uani 1 1 d . . . H28A H -0.4844 0.8227 1.3254 0.041 Uiso 1 1 calc R . . H28B H -0.2779 0.8336 1.3210 0.041 Uiso 1 1 calc R . . O29 O -0.3686(6) 0.76507(16) 1.2678(3) 0.0345(11) Uani 1 1 d . . . C30 C -0.5212(9) 0.7312(2) 1.2609(5) 0.0369(17) Uani 1 1 d . . . H30A H -0.5928 0.7311 1.1940 0.044 Uiso 1 1 calc R . . H30B H -0.6002 0.7439 1.3034 0.044 Uiso 1 1 calc R . . C31 C -0.4586(9) 0.6773(2) 1.2896(5) 0.0380(17) Uani 1 1 d . . . H31A H -0.5645 0.6538 1.2829 0.046 Uiso 1 1 calc R . . H31B H -0.3800 0.6644 1.2469 0.046 Uiso 1 1 calc R . . O32 O -0.3609(6) 0.67747(15) 1.3862(3) 0.0335(11) Uani 1 1 d . . . C33 C -0.2941(9) 0.6281(2) 1.4249(4) 0.0315(16) Uani 1 1 d . . . H33A H -0.2567 0.6068 1.3744 0.038 Uiso 1 1 calc R . . H33B H -0.3904 0.6092 1.4485 0.038 Uiso 1 1 calc R . . C34 C -0.1376(9) 0.6372(2) 1.5047(4) 0.0311(16) Uani 1 1 d . . . H34A H -0.0869 0.6036 1.5315 0.037 Uiso 1 1 calc R . . H34B H -0.1769 0.6569 1.5566 0.037 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 P1 0.0370(10) 0.0406(11) 0.0236(10) 0.0052(8) 0.0081(8) 0.0021(9) F11 0.045(3) 0.083(3) 0.036(3) 0.011(2) 0.0119(19) 0.019(2) F12 0.035(3) 0.125(4) 0.063(3) 0.001(3) 0.018(2) 0.017(3) F13 0.096(4) 0.036(2) 0.055(3) 0.013(2) 0.010(2) 0.003(2) F14 0.049(3) 0.046(2) 0.040(2) -0.0027(19) 0.0100(19) 0.0013(19) F15 0.102(4) 0.042(3) 0.043(3) 0.009(2) 0.006(2) -0.021(2) F16 0.060(3) 0.073(3) 0.007(2) 0.0010(18) 0.0014(17) 0.002(2) O1 0.049(3) 0.047(3) 0.033(3) -0.015(2) 0.010(2) 0.007(2) O2 0.064(3) 0.053(3) 0.015(3) 0.001(2) 0.002(2) -0.002(3) N3 0.042(4) 0.034(3) 0.039(4) -0.007(3) 0.016(3) -0.009(3) C4 0.032(4) 0.030(4) 0.018(4) -0.008(3) 0.008(3) -0.002(3) C5 0.035(4) 0.030(4) 0.014(4) -0.001(3) 0.003(3) -0.001(3) C6 0.035(4) 0.028(4) 0.031(4) 0.005(3) 0.008(3) 0.001(3) C7 0.025(3) 0.035(4) 0.024(4) -0.001(3) 0.010(3) -0.004(3) C8 0.036(4) 0.021(3) 0.039(4) 0.001(3) 0.008(3) 0.001(3) C9 0.035(4) 0.035(4) 0.014(4) 0.000(3) 0.002(3) -0.004(3) N10 0.033(3) 0.031(3) 0.015(3) -0.004(2) 0.006(2) -0.004(2) N11 0.039(3) 0.030(3) 0.013(3) -0.002(2) 0.004(2) -0.001(2) C12 0.028(4) 0.028(4) 0.039(4) 0.001(3) 0.016(3) -0.003(3) C13 0.030(4) 0.027(4) 0.035(4) 0.008(3) 0.012(3) 0.002(3) C14 0.029(4) 0.026(3) 0.021(4) 0.000(3) 0.000(3) 0.002(3) C15 0.031(4) 0.024(3) 0.027(4) -0.005(3) 0.012(3) -0.003(3) C16 0.031(4) 0.027(3) 0.021(4) 0.004(3) 0.005(3) 0.004(3) C17 0.034(4) 0.025(3) 0.018(4) -0.004(3) 0.006(3) -0.001(3) O18 0.052(3) 0.027(2) 0.025(3) 0.0070(19) 0.014(2) 0.009(2) C19 0.074(6) 0.035(4) 0.030(4) 0.010(3) 0.018(4) 0.019(4) N20 0.031(3) 0.028(3) 0.023(3) 0.002(2) 0.008(2) 0.001(2) C21 0.035(4) 0.036(4) 0.018(4) -0.001(3) 0.000(3) 0.003(3) C22 0.037(4) 0.044(4) 0.009(3) 0.002(3) -0.004(3) 0.002(3) O23 0.040(3) 0.039(3) 0.037(3) 0.007(2) 0.008(2) -0.004(2) C24 0.044(4) 0.030(4) 0.047(5) 0.000(3) -0.002(4) -0.002(3) C25 0.052(5) 0.027(4) 0.048(5) 0.004(3) 0.005(4) -0.003(3) O26 0.032(3) 0.027(2) 0.028(3) -0.0004(19) 0.0024(19) -0.001(2) C27 0.033(4) 0.032(4) 0.037(4) -0.002(3) 0.011(3) 0.005(3) C28 0.035(4) 0.033(4) 0.032(4) -0.003(3) -0.001(3) 0.001(3) O29 0.036(3) 0.030(3) 0.038(3) -0.004(2) 0.011(2) -0.005(2) C30 0.033(4) 0.034(4) 0.042(5) 0.002(3) 0.003(3) -0.003(3) C31 0.031(4) 0.029(4) 0.051(5) -0.004(3) 0.003(3) -0.005(3) O32 0.038(3) 0.028(2) 0.035(3) 0.000(2) 0.008(2) 0.000(2) C33 0.042(4) 0.028(4) 0.028(4) -0.001(3) 0.016(3) -0.002(3) C34 0.041(4) 0.028(4) 0.030(4) 0.004(3) 0.021(3) 0.000(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 P1 F12 1.580(4) . ? P1 F16 1.586(4) . ? P1 F13 1.590(4) . ? P1 F15 1.590(4) . ? P1 F11 1.591(4) . ? P1 F14 1.601(4) . ? O1 N3 1.230(6) . ? O2 N3 1.239(7) . ? N3 C4 1.450(7) . ? C4 C9 1.386(8) . ? C4 C5 1.405(8) . ? C5 C6 1.382(8) . ? C6 C7 1.387(8) . ? C7 C8 1.382(8) . ? C7 N10 1.432(7) . ? C8 C9 1.405(8) . ? N10 N11 1.253(6) . ? N11 C12 1.445(7) . ? C12 C13 1.374(8) . ? C12 C17 1.379(8) . ? C13 C14 1.373(8) . ? C14 C15 1.390(8) . ? C15 C16 1.400(8) . ? C15 N20 1.460(7) . ? C16 O18 1.342(6) . ? C16 C17 1.399(8) . ? O18 C19 1.438(7) . ? N20 C34 1.518(7) . ? N20 C21 1.527(7) . ? C21 C22 1.507(8) . ? C22 O23 1.423(7) . ? O23 C24 1.431(7) . ? C24 C25 1.506(9) . ? C25 O26 1.416(7) . ? O26 C27 1.415(7) . ? C27 C28 1.527(8) . ? C28 O29 1.432(7) . ? O29 C30 1.431(7) . ? C30 C31 1.495(8) . ? C31 O32 1.416(7) . ? O32 C33 1.433(7) . ? C33 C34 1.474(9) . ? 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 F12 P1 F16 89.9(2) . . ? F12 P1 F13 90.6(3) . . ? F16 P1 F13 89.3(2) . . ? F12 P1 F15 90.5(3) . . ? F16 P1 F15 91.0(2) . . ? F13 P1 F15 178.9(3) . . ? F12 P1 F11 179.7(3) . . ? F16 P1 F11 90.3(2) . . ? F13 P1 F11 89.6(2) . . ? F15 P1 F11 89.3(3) . . ? F12 P1 F14 90.3(2) . . ? F16 P1 F14 179.2(2) . . ? F13 P1 F14 90.0(2) . . ? F15 P1 F14 89.8(2) . . ? F11 P1 F14 89.5(2) . . ? O1 N3 O2 124.4(5) . . ? O1 N3 C4 118.0(6) . . ? O2 N3 C4 117.6(6) . . ? C9 C4 C5 122.8(5) . . ? C9 C4 N3 119.4(6) . . ? C5 C4 N3 117.8(5) . . ? C6 C5 C4 117.5(6) . . ? C5 C6 C7 120.4(6) . . ? C8 C7 C6 121.8(6) . . ? C8 C7 N10 123.1(6) . . ? C6 C7 N10 115.1(6) . . ? C7 C8 C9 118.9(6) . . ? C4 C9 C8 118.4(6) . . ? N11 N10 C7 114.5(5) . . ? N10 N11 C12 112.9(5) . . ? C13 C12 C17 121.8(6) . . ? C13 C12 N11 116.7(6) . . ? C17 C12 N11 121.5(5) . . ? C14 C13 C12 120.6(6) . . ? C13 C14 C15 118.7(6) . . ? C14 C15 C16 121.2(5) . . ? C14 C15 N20 116.2(5) . . ? C16 C15 N20 122.5(5) . . ? O18 C16 C17 124.1(5) . . ? O18 C16 C15 116.8(5) . . ? C17 C16 C15 119.1(6) . . ? C12 C17 C16 118.6(6) . . ? C16 O18 C19 117.8(5) . . ? C15 N20 C34 115.2(5) . . ? C15 N20 C21 113.9(5) . . ? C34 N20 C21 108.6(5) . . ? C22 C21 N20 111.9(5) . . ? O23 C22 C21 111.7(5) . . ? C22 O23 C24 114.6(5) . . ? O23 C24 C25 107.8(5) . . ? O26 C25 C24 110.0(5) . . ? C27 O26 C25 113.3(5) . . ? O26 C27 C28 114.2(5) . . ? O29 C28 C27 114.6(5) . . ? C30 O29 C28 114.5(5) . . ? O29 C30 C31 110.1(5) . . ? O32 C31 C30 109.4(5) . . ? C31 O32 C33 116.0(4) . . ? O32 C33 C34 108.3(5) . . ? C33 C34 N20 109.4(5) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.416 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.097 data_thornaam _database_code_CSD 166866 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 N3 O7' _chemical_formula_weight 472.51 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.2110(16) _cell_length_b 23.167(6) _cell_length_c 14.329(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.988(9) _cell_angle_gamma 90.00 _cell_volume 2370.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 795 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 20.2 _exptl_crystal_description plate _exptl_crystal_colour red/orange _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1004 _exptl_absorpt_coefficient_mu 0.098 _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 153(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 9665 _diffrn_reflns_av_R_equivalents 0.0993 _diffrn_reflns_av_sigmaI/netI 0.1578 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4134 _reflns_number_gt 1554 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0670P)^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 4134 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1808 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1853 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 0.897 _refine_ls_restrained_S_all 0.897 _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 0.8134(6) 0.18891(18) 0.7761(2) 0.0631(12) Uani 1 1 d . . . O2 O 0.7643(5) 0.10635(17) 0.8335(2) 0.0534(11) Uani 1 1 d . . . C3 C 0.7865(6) 0.1373(2) 0.7672(3) 0.0211(11) Uani 1 1 d . . . C4 C 0.7826(7) 0.1108(2) 0.6749(3) 0.0324(12) Uani 1 1 d . . . C5 C 0.8152(7) 0.1455(2) 0.6004(3) 0.0367(13) Uani 1 1 d . . . H5A H 0.8396 0.1856 0.6092 0.044 Uiso 1 1 calc R . . C6 C 0.8111(7) 0.1201(2) 0.5126(3) 0.0383(13) Uani 1 1 d . . . H6A H 0.8325 0.1430 0.4602 0.046 Uiso 1 1 calc R . . C7 C 0.7763(7) 0.0618(2) 0.5004(3) 0.0315(12) Uani 1 1 d . . . C8 C 0.7432(7) 0.0274(2) 0.5768(3) 0.0400(14) Uani 1 1 d . . . H8A H 0.7181 -0.0127 0.5688 0.048 Uiso 1 1 calc R . . C9 C 0.7479(7) 0.0532(2) 0.6645(3) 0.0412(14) Uani 1 1 d . . . H9A H 0.7269 0.0307 0.7174 0.049 Uiso 1 1 calc R . . N10 N 0.7740(6) 0.04119(18) 0.4065(3) 0.0351(11) Uani 1 1 d . . . N11 N 0.7437(5) -0.01285(18) 0.3993(3) 0.0351(11) Uani 1 1 d . . . C12 C 0.7426(7) -0.0348(2) 0.3079(3) 0.0280(12) Uani 1 1 d . . . C13 C 0.7282(7) -0.0937(2) 0.2986(3) 0.0328(13) Uani 1 1 d . . . H13A H 0.7112 -0.1163 0.3521 0.039 Uiso 1 1 calc R . . C14 C 0.7378(6) -0.1210(2) 0.2138(3) 0.0315(12) Uani 1 1 d . . . H14A H 0.7290 -0.1619 0.2100 0.038 Uiso 1 1 calc R . . C15 C 0.7605(6) -0.0888(2) 0.1331(3) 0.0279(12) Uani 1 1 d . . . C16 C 0.7542(6) -0.0281(2) 0.1417(3) 0.0279(12) Uani 1 1 d . . . C17 C 0.7499(6) -0.0011(2) 0.2263(3) 0.0298(12) Uani 1 1 d . . . H17A H 0.7518 0.0398 0.2301 0.036 Uiso 1 1 calc R . . O18 O 0.7494(4) 0.00221(13) 0.0581(2) 0.0326(8) Uani 1 1 d . . . C19 C 0.6637(7) 0.05854(19) 0.0550(3) 0.0370(13) Uani 1 1 d . . . H19A H 0.6426 0.0723 -0.0103 0.055 Uiso 1 1 calc R . . H19B H 0.7466 0.0855 0.0936 0.055 Uiso 1 1 calc R . . H19C H 0.5437 0.0561 0.0795 0.055 Uiso 1 1 calc R . . N20 N 0.7785(5) -0.11486(16) 0.0470(2) 0.0285(10) Uani 1 1 d . . . C21 C 0.9164(6) -0.0926(2) -0.0107(3) 0.0312(12) Uani 1 1 d . . . H21A H 1.0092 -0.1233 -0.0174 0.037 Uiso 1 1 calc R . . H21B H 0.9841 -0.0599 0.0228 0.037 Uiso 1 1 calc R . . C22 C 0.8315(7) -0.0727(2) -0.1080(3) 0.0324(12) Uani 1 1 d . . . H22A H 0.7466 -0.0396 -0.1028 0.039 Uiso 1 1 calc R . . H22B H 0.9316 -0.0601 -0.1442 0.039 Uiso 1 1 calc R . . O23 O 0.7300(4) -0.11934(13) -0.1551(2) 0.0344(9) Uani 1 1 d . . . C24 C 0.6501(7) -0.1058(2) -0.2484(3) 0.0376(13) Uani 1 1 d . . . H24A H 0.7501 -0.1002 -0.2884 0.045 Uiso 1 1 calc R . . H24B H 0.5766 -0.0697 -0.2491 0.045 Uiso 1 1 calc R . . C25 C 0.5243(7) -0.1553(2) -0.2860(3) 0.0406(14) Uani 1 1 d . . . H25A H 0.4825 -0.1500 -0.3543 0.049 Uiso 1 1 calc R . . H25B H 0.5932 -0.1923 -0.2769 0.049 Uiso 1 1 calc R . . O26 O 0.3664(5) -0.15618(14) -0.2362(2) 0.0383(9) Uani 1 1 d . . . C27 C 0.2579(7) -0.2065(2) -0.2568(3) 0.0417(14) Uani 1 1 d . . . H27A H 0.3363 -0.2412 -0.2413 0.050 Uiso 1 1 calc R . . H27B H 0.2090 -0.2077 -0.3249 0.050 Uiso 1 1 calc R . . C28 C 0.0978(8) -0.2062(2) -0.1998(4) 0.0465(15) Uani 1 1 d . . . H28A H 0.0251 -0.1701 -0.2132 0.056 Uiso 1 1 calc R . . H28B H 0.0137 -0.2390 -0.2198 0.056 Uiso 1 1 calc R . . O29 O 0.1579(5) -0.21016(14) -0.1001(2) 0.0429(9) Uani 1 1 d . . . O30 O 0.5059(5) -0.24966(13) 0.0258(2) 0.0386(9) Uani 1 1 d . . . C30 C 0.2020(8) -0.2675(2) -0.0697(4) 0.0460(15) Uani 1 1 d . . . H30A H 0.2736 -0.2868 -0.1150 0.055 Uiso 1 1 calc R . . H30B H 0.0850 -0.2896 -0.0677 0.055 Uiso 1 1 calc R . . C31 C 0.3162(7) -0.2671(2) 0.0267(4) 0.0433(14) Uani 1 1 d . . . H31A H 0.2568 -0.2405 0.0679 0.052 Uiso 1 1 calc R . . H31B H 0.3151 -0.3063 0.0541 0.052 Uiso 1 1 calc R . . C33 C 0.5336(7) -0.18871(19) 0.0242(4) 0.0378(13) Uani 1 1 d . . . H33A H 0.4778 -0.1703 0.0761 0.045 Uiso 1 1 calc R . . H33B H 0.4724 -0.1725 -0.0363 0.045 Uiso 1 1 calc R . . C34 C 0.7404(7) -0.17710(19) 0.0355(3) 0.0310(12) Uani 1 1 d . . . H34A H 0.8029 -0.1981 0.0914 0.037 Uiso 1 1 calc R . . H34B H 0.7923 -0.1915 -0.0205 0.037 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 0.083(3) 0.064(3) 0.044(2) -0.014(2) 0.012(2) 0.007(3) O2 0.049(3) 0.070(3) 0.041(2) -0.008(2) 0.0036(19) 0.009(2) C3 0.025(3) 0.027(3) 0.011(2) -0.004(2) 0.000(2) 0.007(2) C4 0.028(3) 0.040(3) 0.029(3) -0.001(3) 0.002(2) 0.002(3) C5 0.037(3) 0.034(3) 0.038(3) -0.001(3) 0.002(2) -0.001(3) C6 0.039(4) 0.044(3) 0.033(3) 0.001(3) 0.007(2) -0.003(3) C7 0.031(3) 0.035(3) 0.029(3) -0.006(2) 0.004(2) -0.002(3) C8 0.054(4) 0.030(3) 0.037(3) 0.003(2) 0.008(3) -0.005(3) C9 0.051(4) 0.044(4) 0.030(3) 0.002(3) 0.008(3) -0.006(3) N10 0.037(3) 0.040(3) 0.028(2) -0.001(2) 0.0022(19) -0.004(2) N11 0.033(3) 0.034(3) 0.039(3) -0.001(2) 0.007(2) -0.001(2) C12 0.032(3) 0.027(3) 0.025(3) -0.003(2) 0.004(2) -0.001(2) C13 0.038(3) 0.031(3) 0.029(3) 0.004(2) 0.006(2) 0.003(2) C14 0.033(3) 0.025(3) 0.037(3) 0.000(2) 0.005(2) 0.005(2) C15 0.020(3) 0.033(3) 0.029(3) 0.000(2) -0.002(2) 0.003(2) C16 0.030(3) 0.024(3) 0.029(3) 0.003(2) 0.002(2) 0.000(2) C17 0.030(3) 0.030(3) 0.030(3) -0.003(2) 0.004(2) -0.001(2) O18 0.039(2) 0.0272(19) 0.0318(18) 0.0002(15) 0.0043(15) 0.0034(17) C19 0.033(3) 0.034(3) 0.043(3) 0.008(2) 0.000(2) 0.006(3) N20 0.030(3) 0.028(2) 0.028(2) -0.0022(18) 0.0051(18) -0.0015(19) C21 0.028(3) 0.034(3) 0.031(3) 0.001(2) 0.001(2) -0.002(2) C22 0.031(3) 0.032(3) 0.034(3) -0.002(2) 0.006(2) -0.005(2) O23 0.035(2) 0.037(2) 0.0295(18) -0.0034(16) -0.0028(15) -0.0015(17) C24 0.038(3) 0.046(3) 0.027(3) 0.000(2) 0.000(2) 0.002(3) C25 0.039(4) 0.048(4) 0.033(3) -0.007(3) 0.002(3) 0.005(3) O26 0.034(2) 0.037(2) 0.043(2) -0.0092(16) 0.0013(17) -0.0016(17) C27 0.039(4) 0.036(3) 0.047(3) -0.012(3) -0.004(3) -0.002(3) C28 0.044(4) 0.045(4) 0.048(3) -0.006(3) -0.003(3) -0.002(3) O29 0.039(2) 0.042(2) 0.046(2) -0.0115(18) 0.0008(17) 0.0019(18) O30 0.036(2) 0.027(2) 0.053(2) 0.0000(16) 0.0045(18) -0.0047(16) C30 0.037(4) 0.031(3) 0.068(4) -0.007(3) 0.000(3) -0.004(3) C31 0.035(4) 0.045(4) 0.050(4) 0.001(3) 0.010(3) -0.009(3) C33 0.043(4) 0.022(3) 0.049(3) 0.000(2) 0.009(3) 0.005(2) C34 0.032(3) 0.026(3) 0.034(3) 0.000(2) 0.001(2) 0.003(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 1.216(5) . ? O2 C3 1.218(5) . ? C3 C4 1.455(6) . ? C4 C9 1.360(6) . ? C4 C5 1.383(6) . ? C5 C6 1.387(6) . ? C6 C7 1.380(6) . ? C7 C8 1.402(6) . ? C7 N10 1.426(5) . ? C8 C9 1.388(6) . ? N10 N11 1.273(5) . ? N11 C12 1.404(5) . ? C12 C13 1.373(6) . ? C12 C17 1.413(6) . ? C13 C14 1.379(6) . ? C14 C15 1.404(6) . ? C15 N20 1.396(5) . ? C15 C16 1.413(6) . ? C16 C17 1.367(6) . ? C16 O18 1.385(5) . ? O18 C19 1.442(5) . ? N20 C21 1.472(5) . ? N20 C34 1.473(5) . ? C21 C22 1.515(6) . ? C22 O23 1.421(5) . ? O23 C24 1.416(5) . ? C24 C25 1.514(6) . ? C25 O26 1.426(5) . ? O26 C27 1.413(5) . ? C27 C28 1.504(7) . ? C28 O29 1.438(6) . ? O29 C30 1.421(5) . ? O30 C33 1.427(5) . ? O30 C31 1.428(5) . ? C30 C31 1.507(7) . ? C33 C34 1.501(6) . ? 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 O1 C3 O2 122.2(4) . . ? O1 C3 C4 119.5(5) . . ? O2 C3 C4 118.2(5) . . ? C9 C4 C5 122.3(4) . . ? C9 C4 C3 119.5(5) . . ? C5 C4 C3 118.2(5) . . ? C4 C5 C6 118.0(5) . . ? C7 C6 C5 120.7(5) . . ? C6 C7 C8 120.4(4) . . ? C6 C7 N10 115.2(4) . . ? C8 C7 N10 124.5(4) . . ? C9 C8 C7 118.5(5) . . ? C4 C9 C8 120.2(5) . . ? N11 N10 C7 112.7(4) . . ? N10 N11 C12 114.3(4) . . ? C13 C12 N11 116.2(4) . . ? C13 C12 C17 118.7(4) . . ? N11 C12 C17 125.1(4) . . ? C12 C13 C14 121.9(5) . . ? C13 C14 C15 120.5(4) . . ? N20 C15 C14 122.3(4) . . ? N20 C15 C16 121.0(4) . . ? C14 C15 C16 116.6(4) . . ? C17 C16 O18 122.2(4) . . ? C17 C16 C15 122.5(4) . . ? O18 C16 C15 115.2(4) . . ? C16 C17 C12 119.2(4) . . ? C16 O18 C19 116.4(3) . . ? C15 N20 C21 119.9(4) . . ? C15 N20 C34 118.9(4) . . ? C21 N20 C34 114.2(4) . . ? N20 C21 C22 113.9(4) . . ? O23 C22 C21 108.7(4) . . ? C24 O23 C22 113.2(3) . . ? O23 C24 C25 108.3(4) . . ? O26 C25 C24 108.3(4) . . ? C27 O26 C25 111.4(4) . . ? O26 C27 C28 109.0(4) . . ? O29 C28 C27 113.1(4) . . ? C30 O29 C28 112.8(4) . . ? C33 O30 C31 114.6(4) . . ? O29 C30 C31 110.2(4) . . ? O30 C31 C30 113.3(4) . . ? O30 C33 C34 108.4(4) . . ? N20 C34 C33 110.8(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.292 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.069 data_thorri6m _database_code_CSD 166867 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H30 N4 O7' _chemical_formula_weight 474.51 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.161(5) _cell_length_b 7.521(3) _cell_length_c 22.967(9) _cell_angle_alpha 90.00 _cell_angle_beta 105.703(8) _cell_angle_gamma 90.00 _cell_volume 2354.9(15) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2027 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 21 _exptl_crystal_description Block _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9725 _exptl_absorpt_correction_T_max 0.9901 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 14543 _diffrn_reflns_av_R_equivalents 0.0793 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 22.49 _reflns_number_total 3075 _reflns_number_gt 1772 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1027P)^2^+3.0465P] 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 3075 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.0694 _refine_ls_wR_factor_ref 0.2201 _refine_ls_wR_factor_gt 0.1737 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 -0.0871(4) 1.6132(6) -0.1069(2) 0.1061(19) Uani 1 1 d . . . O2 O -0.1546(3) 1.4225(6) -0.1738(2) 0.0757(13) Uani 1 1 d . . . N3 N -0.0952(4) 1.4640(7) -0.1269(2) 0.0558(13) Uani 1 1 d . . . C4 C -0.0283(4) 1.3282(7) -0.0931(2) 0.0444(14) Uani 1 1 d . . . C5 C 0.0505(4) 1.3741(9) -0.0480(3) 0.0619(16) Uani 1 1 d . . . H5 H 0.0639 1.4946 -0.0362 0.074 Uiso 1 1 calc R . . C6 C 0.1133(4) 1.2319(13) -0.0184(3) 0.085(2) Uani 1 1 d . . . H6 H 0.1691 1.2542 0.0145 0.101 Uiso 1 1 calc R . . C7 C 0.0885(6) 1.0561(9) -0.0405(4) 0.078(2) Uani 1 1 d . . . C8 C 0.0108(5) 1.0243(10) -0.0846(4) 0.079(2) Uani 1 1 d . . . H8 H -0.0035 0.9057 -0.0983 0.094 Uiso 1 1 calc R . . C9 C -0.0486(4) 1.1545(8) -0.1107(3) 0.0600(16) Uani 1 1 d . . . H9 H -0.1060 1.1275 -0.1421 0.072 Uiso 1 1 calc R . . N10 N 0.1596(5) 0.8966(6) -0.0147(3) 0.0777(18) Uani 1 1 d . . . N11 N 0.2021(4) 0.9411(9) 0.0318(2) 0.085(2) Uani 1 1 d . . . C12 C 0.2680(4) 0.7771(7) 0.0529(3) 0.0483(15) Uani 1 1 d . . . C13 C 0.3103(4) 0.7831(7) 0.1136(3) 0.0471(14) Uani 1 1 d . . . H13 H 0.2970 0.8799 0.1367 0.057 Uiso 1 1 calc R . . C14 C 0.3720(4) 0.6494(7) 0.1412(2) 0.0427(13) Uani 1 1 d . . . H14 H 0.3995 0.6530 0.1838 0.051 Uiso 1 1 calc R . . C15 C 0.3956(3) 0.5069(6) 0.1080(2) 0.0336(12) Uani 1 1 d . . . C16 C 0.3563(3) 0.5105(6) 0.0452(2) 0.0397(13) Uani 1 1 d . . . C17 C 0.2908(4) 0.6418(7) 0.0177(2) 0.0461(14) Uani 1 1 d . . . H17 H 0.2618 0.6394 -0.0248 0.055 Uiso 1 1 calc R . . O18 O 0.3908(2) 0.3838(4) 0.01345(14) 0.0468(9) Uani 1 1 d . . . C19 C 0.3752(4) 0.4122(8) -0.0497(2) 0.0570(16) Uani 1 1 d . . . H19A H 0.4164 0.3302 -0.0653 0.085 Uiso 1 1 calc R . . H19B H 0.3925 0.5350 -0.0568 0.085 Uiso 1 1 calc R . . H19C H 0.3061 0.3909 -0.0706 0.085 Uiso 1 1 calc R . . N20 N 0.4601(3) 0.3750(5) 0.13638(16) 0.0357(10) Uani 1 1 d . . . C21 C 0.4410(4) 0.1874(6) 0.1186(2) 0.0391(13) Uani 1 1 d . . . H21A H 0.3774 0.1793 0.0873 0.047 Uiso 1 1 calc R . . H21B H 0.4353 0.1184 0.1542 0.047 Uiso 1 1 calc R . . C22 C 0.5190(4) 0.1048(7) 0.0943(2) 0.0448(13) Uani 1 1 d . . . H22A H 0.5030 -0.0216 0.0842 0.054 Uiso 1 1 calc R . . H22B H 0.5224 0.1671 0.0569 0.054 Uiso 1 1 calc R . . O23 O 0.6109(2) 0.1177(4) 0.13873(15) 0.0470(9) Uani 1 1 d . . . C24 C 0.6903(4) 0.0537(7) 0.1185(3) 0.0514(15) Uani 1 1 d . . . H24A H 0.6851 0.0992 0.0773 0.062 Uiso 1 1 calc R . . H24B H 0.6882 -0.0778 0.1167 0.062 Uiso 1 1 calc R . . C25 C 0.7837(4) 0.1125(8) 0.1602(3) 0.0582(16) Uani 1 1 d . . . H25A H 0.7836 0.0866 0.2025 0.070 Uiso 1 1 calc R . . H25B H 0.8390 0.0473 0.1515 0.070 Uiso 1 1 calc R . . O26 O 0.7955(3) 0.2989(5) 0.15301(16) 0.0568(11) Uani 1 1 d . B . C27 C 0.8833(4) 0.3650(11) 0.1916(3) 0.080(2) Uani 1 1 d . . . H27A H 0.9403 0.3174 0.1795 0.096 Uiso 1 1 calc R A 1 H27B H 0.8892 0.3282 0.2338 0.096 Uiso 1 1 calc R A 1 C28 C 0.8811(5) 0.5671(10) 0.1869(3) 0.086(3) Uani 0.768(9) 1 d P B 2 H28A H 0.9414 0.6137 0.2155 0.103 Uiso 0.768(9) 1 calc PR B 2 H28B H 0.8839 0.5995 0.1456 0.103 Uiso 0.768(9) 1 calc PR B 2 O29 O 0.7979(3) 0.6577(6) 0.1986(2) 0.0433(17) Uani 0.768(9) 1 d P B 2 C30 C 0.8043(5) 0.6717(11) 0.2572(3) 0.076(2) Uani 0.768(9) 1 d P B 2 H30A H 0.8531 0.7651 0.2745 0.091 Uiso 0.768(9) 1 calc PR B 2 H30B H 0.8300 0.5581 0.2770 0.091 Uiso 0.768(9) 1 calc PR B 2 C28' C 0.8811(5) 0.5671(10) 0.1869(3) 0.086(3) Uani 0.23 1 d P B 1 H28C H 0.8306 0.6167 0.1520 0.103 Uiso 0.232(9) 1 calc PR B 1 H28D H 0.9457 0.6252 0.1928 0.103 Uiso 0.232(9) 1 calc PR B 1 O29' O 0.8454(12) 0.535(2) 0.2494(7) 0.055(6) Uani 0.232(9) 1 d P B 1 C30' C 0.8043(5) 0.6717(11) 0.2572(3) 0.076(2) Uani 0.23 1 d P B 1 H30C H 0.7983 0.7389 0.2193 0.091 Uiso 0.232(9) 1 calc PR B 1 H30D H 0.8550 0.7354 0.2884 0.091 Uiso 0.232(9) 1 calc PR B 1 C31 C 0.7138(4) 0.7137(8) 0.2727(3) 0.0526(15) Uani 1 1 d . . . H31A H 0.7300 0.7472 0.3159 0.063 Uiso 1 1 calc R B 1 H31B H 0.6831 0.8183 0.2488 0.063 Uiso 1 1 calc R B 1 O32 O 0.6444(3) 0.5732(5) 0.26233(14) 0.0484(10) Uani 1 1 d . B . C33 C 0.5981(3) 0.5386(7) 0.2007(2) 0.0405(13) Uani 1 1 d . . . H33A H 0.6465 0.4924 0.1804 0.049 Uiso 1 1 calc R B . H33B H 0.5693 0.6493 0.1800 0.049 Uiso 1 1 calc R . . C34 C 0.5189(3) 0.4028(6) 0.1980(2) 0.0377(12) Uani 1 1 d . B . H34A H 0.5492 0.2888 0.2150 0.045 Uiso 1 1 calc R . . H34B H 0.4761 0.4436 0.2231 0.045 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 0.172(5) 0.044(3) 0.087(4) 0.000(3) 0.008(3) 0.030(3) O2 0.065(3) 0.086(3) 0.065(3) 0.017(3) -0.001(2) 0.000(2) N3 0.068(3) 0.051(3) 0.051(3) 0.013(3) 0.021(3) 0.012(3) C4 0.047(3) 0.040(3) 0.048(3) 0.012(3) 0.015(3) 0.012(3) C5 0.063(4) 0.068(4) 0.054(4) 0.011(3) 0.015(3) 0.001(3) C6 0.035(3) 0.166(8) 0.051(4) 0.027(5) 0.008(3) 0.010(4) C7 0.095(6) 0.047(4) 0.109(6) 0.037(4) 0.058(5) 0.022(4) C8 0.055(4) 0.063(5) 0.127(7) 0.020(5) 0.038(4) 0.010(4) C9 0.055(4) 0.044(4) 0.089(5) 0.008(3) 0.034(3) 0.008(3) N10 0.124(5) 0.035(3) 0.097(5) -0.021(3) 0.069(4) -0.023(3) N11 0.057(3) 0.150(6) 0.048(3) -0.024(4) 0.017(3) -0.053(4) C12 0.039(3) 0.028(3) 0.077(4) 0.016(3) 0.015(3) 0.013(2) C13 0.048(3) 0.032(3) 0.066(4) -0.003(3) 0.022(3) 0.000(3) C14 0.047(3) 0.038(3) 0.046(3) -0.006(3) 0.018(3) -0.001(3) C15 0.036(3) 0.027(3) 0.037(3) -0.001(2) 0.009(2) 0.000(2) C16 0.044(3) 0.033(3) 0.042(3) -0.006(3) 0.011(3) -0.004(2) C17 0.041(3) 0.043(3) 0.050(3) 0.005(3) 0.006(3) -0.006(3) O18 0.067(2) 0.039(2) 0.0313(19) -0.0025(17) 0.0075(17) 0.0049(18) C19 0.081(4) 0.056(4) 0.032(3) -0.004(3) 0.012(3) 0.003(3) N20 0.045(2) 0.027(2) 0.033(2) -0.0025(18) 0.0070(19) -0.0011(19) C21 0.051(3) 0.023(3) 0.041(3) 0.002(2) 0.010(3) -0.005(2) C22 0.058(3) 0.028(3) 0.047(3) -0.004(2) 0.012(3) -0.002(3) O23 0.050(2) 0.042(2) 0.049(2) 0.0011(17) 0.0134(19) 0.0045(17) C24 0.057(4) 0.037(3) 0.064(4) 0.000(3) 0.022(3) 0.010(3) C25 0.050(3) 0.057(4) 0.068(4) 0.000(3) 0.016(3) 0.015(3) O26 0.052(2) 0.058(3) 0.060(2) -0.015(2) 0.014(2) -0.0067(19) C27 0.051(4) 0.122(7) 0.071(4) -0.028(4) 0.024(3) -0.014(4) C28 0.064(4) 0.099(6) 0.116(6) -0.052(5) 0.059(4) -0.032(4) O29 0.045(3) 0.042(3) 0.044(3) -0.001(2) 0.014(2) -0.003(2) C30 0.057(4) 0.088(6) 0.082(5) -0.037(4) 0.019(4) -0.011(4) C28' 0.064(4) 0.099(6) 0.116(6) -0.052(5) 0.059(4) -0.032(4) O29' 0.055(10) 0.040(11) 0.064(12) -0.003(8) 0.010(9) 0.004(8) C30' 0.057(4) 0.088(6) 0.082(5) -0.037(4) 0.019(4) -0.011(4) C31 0.050(3) 0.056(4) 0.056(4) -0.021(3) 0.020(3) -0.015(3) O32 0.062(2) 0.051(2) 0.0302(19) -0.0070(16) 0.0084(17) -0.0169(18) C33 0.047(3) 0.041(3) 0.032(3) 0.002(2) 0.008(2) -0.004(2) C34 0.045(3) 0.036(3) 0.032(3) 0.002(2) 0.009(2) -0.003(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 N3 1.206(6) . ? O2 N3 1.213(6) . ? N3 C4 1.465(7) . ? C4 C5 1.347(7) . ? C4 C9 1.375(8) . ? C5 C6 1.439(9) . ? C6 C7 1.426(10) . ? C7 C8 1.299(10) . ? C7 N10 1.575(9) . ? C8 C9 1.324(8) . ? N10 N11 1.126(6) . ? N11 C12 1.544(8) . ? C12 C13 1.360(7) . ? C12 C17 1.391(7) . ? C13 C14 1.370(7) . ? C14 C15 1.408(7) . ? C15 N20 1.386(6) . ? C15 C16 1.398(6) . ? C16 O18 1.369(6) . ? C16 C17 1.385(7) . ? O18 C19 1.424(6) . ? N20 C34 1.450(6) . ? N20 C21 1.474(6) . ? C21 C22 1.499(7) . ? C22 O23 1.424(6) . ? O23 C24 1.412(6) . ? C24 C25 1.476(7) . ? C25 O26 1.426(6) . ? O26 C27 1.408(7) . ? C27 C28 1.523(10) . ? C28 O29 1.447(7) . ? O29 C30 1.328(7) . ? C30 C31 1.455(8) . ? C31 O32 1.419(6) . ? O32 C33 1.413(5) . ? C33 C34 1.506(6) . ? 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 O1 N3 O2 123.3(5) . . ? O1 N3 C4 117.8(5) . . ? O2 N3 C4 118.9(5) . . ? C5 C4 C9 122.3(5) . . ? C5 C4 N3 120.8(5) . . ? C9 C4 N3 117.0(5) . . ? C4 C5 C6 116.8(6) . . ? C7 C6 C5 117.4(6) . . ? C8 C7 C6 121.5(7) . . ? C8 C7 N10 118.2(7) . . ? C6 C7 N10 120.1(8) . . ? C7 C8 C9 121.1(7) . . ? C8 C9 C4 120.8(6) . . ? N11 N10 C7 104.7(6) . . ? N10 N11 C12 100.5(6) . . ? C13 C12 C17 120.9(5) . . ? C13 C12 N11 110.9(5) . . ? C17 C12 N11 128.1(5) . . ? C12 C13 C14 119.9(5) . . ? C13 C14 C15 121.5(5) . . ? N20 C15 C16 121.8(4) . . ? N20 C15 C14 120.9(4) . . ? C16 C15 C14 117.2(4) . . ? O18 C16 C17 123.0(4) . . ? O18 C16 C15 115.9(4) . . ? C17 C16 C15 121.0(5) . . ? C16 C17 C12 119.2(5) . . ? C16 O18 C19 117.4(4) . . ? C15 N20 C34 119.2(4) . . ? C15 N20 C21 120.4(4) . . ? C34 N20 C21 115.0(4) . . ? N20 C21 C22 113.7(4) . . ? O23 C22 C21 109.1(4) . . ? C24 O23 C22 113.3(4) . . ? O23 C24 C25 109.7(4) . . ? O26 C25 C24 109.4(4) . . ? C27 O26 C25 112.7(5) . . ? O26 C27 C28 108.0(6) . . ? O29 C28 C27 117.3(5) . . ? C30 O29 C28 113.0(5) . . ? O29 C30 C31 116.2(6) . . ? O32 C31 C30 114.4(5) . . ? C33 O32 C31 114.6(4) . . ? O32 C33 C34 107.7(4) . . ? N20 C34 C33 111.2(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.522 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.068