Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 _publ_requested_journal 'Organic & Biomolecular Chemistry' loop_ _publ_author_name F.Heaney 'Desmond Cunningham' 'Patrick McArdle' 'Tomas McCarthy' 'Vickie McKee' _publ_contact_author_name 'Dr F Heaney' _publ_contact_author_address ; Department of Chemistry National University of Ireland Maynooth Co. Kildare REPUBLIC OF IRELAND ; _publ_contact_author_email MARY.F.HEANEY@MAY.IE _publ_section_title ; Bridgehead nitrogen heterocycles which contain the quinazoline moiety - synthesis and cycloaddition of 1,2-dihydroquinazoline 3-oxides ; data_c:\x-ray\kappa\k04pma2\maxus\k04pma2 _database_code_depnum_ccdc_archive 'CCDC 282676' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H26 N2 O7' _chemical_formula_weight 490.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2500(2) _cell_length_b 11.2910(2) _cell_length_c 11.7080(2) _cell_angle_alpha 76.4590(10) _cell_angle_beta 64.7100(10) _cell_angle_gamma 64.8090(10) _cell_volume 1214.28(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _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 150(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 KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21369 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 27.53 _reflns_number_total 5534 _reflns_number_gt 4325 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1029P)^2^+0.8068P] 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 0.020(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5534 _refine_ls_number_parameters 335 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0837 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1938 _refine_ls_wR_factor_gt 0.1751 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.8288(2) 0.0386(2) 0.8098(2) 0.0641(6) Uani 1 1 d . . . O2 O 0.3851(2) 0.40568(19) 0.45690(15) 0.0486(5) Uani 1 1 d . . . O3 O 0.30363(19) 0.51290(16) 0.22257(15) 0.0431(4) Uani 1 1 d . . . O4 O 0.42966(17) 0.29484(16) 0.22172(14) 0.0421(4) Uani 1 1 d . . . O5 O 0.01905(17) 0.26587(18) 0.53222(14) 0.0419(4) Uani 1 1 d . . . O6 O 0.12475(16) 0.34000(15) 0.33396(13) 0.0356(4) Uani 1 1 d . . . O7 O 0.6442(2) 0.4624(2) 0.3543(2) 0.0606(5) Uani 1 1 d D . . N1 N 0.30148(18) 0.22183(18) 0.77018(15) 0.0311(4) Uani 1 1 d . . . N2 N 0.17856(18) 0.30909(18) 0.62657(15) 0.0305(4) Uani 1 1 d . . . C1 C 0.2978(2) 0.1967(2) 0.65603(18) 0.0312(4) Uani 1 1 d . . . H1 H 0.3886 0.1946 0.5849 0.037 Uiso 1 1 calc R . . C2 C 0.1768(2) 0.27046(19) 0.87066(18) 0.0294(4) Uani 1 1 d . . . C3 C 0.1698(2) 0.2611(2) 0.99515(19) 0.0347(5) Uani 1 1 d . . . H3 H 0.2536 0.2185 1.0133 0.042 Uiso 1 1 calc R . . C4 C 0.0415(3) 0.3136(2) 1.0902(2) 0.0379(5) Uani 1 1 d . . . H4 H 0.0381 0.3061 1.1740 0.045 Uiso 1 1 calc R . . C5 C -0.0843(2) 0.3779(2) 1.0677(2) 0.0373(5) Uani 1 1 d . . . H5 H -0.1720 0.4126 1.1354 0.045 Uiso 1 1 calc R . . C6 C -0.0798(2) 0.3903(2) 0.9465(2) 0.0353(5) Uani 1 1 d . . . H6 H -0.1644 0.4349 0.9298 0.042 Uiso 1 1 calc R . . C7 C 0.0500(2) 0.3369(2) 0.84700(18) 0.0306(4) Uani 1 1 d . . . C8 C 0.0618(2) 0.3646(2) 0.71855(19) 0.0323(4) Uani 1 1 d . . . H8 H -0.0180 0.4255 0.6995 0.039 Uiso 1 1 calc R . . C9 C 0.4378(2) 0.1747(2) 0.77969(18) 0.0316(4) Uani 1 1 d . . . C10 C 0.5216(2) 0.0401(2) 0.7795(2) 0.0383(5) Uani 1 1 d . . . H10 H 0.4879 -0.0218 0.7741 0.046 Uiso 1 1 calc R . . C11 C 0.6535(3) -0.0024(2) 0.7872(2) 0.0444(6) Uani 1 1 d . . . H11 H 0.7113 -0.0931 0.7851 0.053 Uiso 1 1 calc R . . C12 C 0.7002(2) 0.0893(3) 0.7980(2) 0.0424(6) Uani 1 1 d . . . C13 C 0.6208(2) 0.2227(2) 0.7918(2) 0.0392(5) Uani 1 1 d . . . H13 H 0.6560 0.2849 0.7939 0.047 Uiso 1 1 calc R . . C14 C 0.4892(2) 0.2648(2) 0.7826(2) 0.0353(5) Uani 1 1 d . . . H14 H 0.4347 0.3559 0.7783 0.042 Uiso 1 1 calc R . . C15 C 0.8712(3) 0.1291(4) 0.8367(3) 0.0659(9) Uani 1 1 d . . . H15A H 0.8873 0.1922 0.7639 0.099 Uiso 1 1 calc R . . H15B H 0.9587 0.0809 0.8532 0.099 Uiso 1 1 calc R . . H15C H 0.7964 0.1760 0.9113 0.099 Uiso 1 1 calc R . . C16 C 0.2809(2) 0.0686(2) 0.6631(2) 0.0339(5) Uani 1 1 d . . . C17 C 0.2364(2) -0.0011(2) 0.7773(2) 0.0411(5) Uani 1 1 d . . . H17 H 0.2174 0.0307 0.8540 0.049 Uiso 1 1 calc R . . C18 C 0.2196(3) -0.1163(3) 0.7802(3) 0.0529(6) Uani 1 1 d . . . H18 H 0.1896 -0.1634 0.8589 0.063 Uiso 1 1 calc R . . C19 C 0.2459(3) -0.1632(3) 0.6702(3) 0.0557(7) Uani 1 1 d . . . H19 H 0.2312 -0.2409 0.6733 0.067 Uiso 1 1 calc R . . C20 C 0.2931(3) -0.0983(3) 0.5566(3) 0.0506(6) Uani 1 1 d . . . H20 H 0.3137 -0.1322 0.4805 0.061 Uiso 1 1 calc R . . C21 C 0.3115(2) 0.0179(2) 0.5517(2) 0.0412(5) Uani 1 1 d . . . H21 H 0.3448 0.0625 0.4723 0.049 Uiso 1 1 calc R . . C22 C 0.1970(2) 0.3411(2) 0.49480(18) 0.0322(5) Uani 1 1 d . . . C23 C 0.3069(2) 0.3848(2) 0.41945(19) 0.0347(5) Uani 1 1 d . . . C24 C 0.3417(2) 0.4071(2) 0.27725(19) 0.0360(5) Uani 1 1 d . . . C25 C 0.4740(3) 0.3025(3) 0.0862(2) 0.0542(7) Uani 1 1 d . . . H25A H 0.3907 0.3352 0.0632 0.081 Uiso 1 1 calc R . . H25B H 0.5361 0.2151 0.0547 0.081 Uiso 1 1 calc R . . H25C H 0.5253 0.3623 0.0482 0.081 Uiso 1 1 calc R . . C26 C 0.1135(2) 0.3171(2) 0.44469(18) 0.0313(4) Uani 1 1 d . . . C27 C -0.0633(3) 0.2358(4) 0.4844(3) 0.0596(8) Uani 1 1 d . . . H27A H -0.1261 0.3173 0.4562 0.089 Uiso 1 1 calc R . . H27B H -0.1200 0.1896 0.5516 0.089 Uiso 1 1 calc R . . H27C H 0.0005 0.1800 0.4130 0.089 Uiso 1 1 calc R . . H7A H 0.565(2) 0.447(4) 0.384(3) 0.089 Uiso 1 1 d D . . H7B H 0.642(3) 0.504(4) 0.412(2) 0.089 Uiso 1 1 d D . . 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 0.0426(10) 0.0797(14) 0.0820(14) 0.0141(11) -0.0397(10) -0.0267(10) O2 0.0593(11) 0.0715(12) 0.0384(9) 0.0055(8) -0.0235(8) -0.0443(10) O3 0.0576(10) 0.0422(9) 0.0332(8) 0.0069(7) -0.0186(7) -0.0248(8) O4 0.0435(9) 0.0479(9) 0.0289(8) 0.0018(6) -0.0132(7) -0.0140(7) O5 0.0417(9) 0.0706(11) 0.0283(8) 0.0058(7) -0.0172(7) -0.0345(8) O6 0.0421(8) 0.0481(9) 0.0252(7) 0.0028(6) -0.0193(6) -0.0201(7) O7 0.0647(13) 0.0557(12) 0.0606(12) -0.0112(9) -0.0198(10) -0.0213(10) N1 0.0321(9) 0.0450(10) 0.0236(8) 0.0020(7) -0.0150(7) -0.0184(8) N2 0.0338(9) 0.0427(10) 0.0217(8) 0.0022(7) -0.0144(7) -0.0181(8) C1 0.0281(9) 0.0472(12) 0.0230(9) -0.0014(8) -0.0118(8) -0.0163(9) C2 0.0389(11) 0.0315(10) 0.0252(9) 0.0042(7) -0.0164(8) -0.0182(8) C3 0.0438(12) 0.0410(11) 0.0267(10) 0.0035(8) -0.0193(9) -0.0188(9) C4 0.0523(13) 0.0411(12) 0.0268(10) 0.0034(8) -0.0197(9) -0.0208(10) C5 0.0437(12) 0.0384(11) 0.0269(10) -0.0025(8) -0.0094(9) -0.0160(10) C6 0.0389(11) 0.0353(11) 0.0309(10) -0.0008(8) -0.0154(9) -0.0114(9) C7 0.0370(10) 0.0339(10) 0.0247(9) 0.0000(7) -0.0141(8) -0.0148(8) C8 0.0372(11) 0.0367(11) 0.0291(10) 0.0007(8) -0.0189(9) -0.0141(9) C9 0.0322(10) 0.0447(12) 0.0256(9) 0.0042(8) -0.0158(8) -0.0193(9) C10 0.0409(12) 0.0391(12) 0.0405(12) 0.0065(9) -0.0213(10) -0.0183(10) C11 0.0413(12) 0.0420(12) 0.0489(13) 0.0075(10) -0.0241(11) -0.0126(10) C12 0.0341(11) 0.0596(15) 0.0392(12) 0.0099(10) -0.0209(10) -0.0218(11) C13 0.0325(11) 0.0572(14) 0.0357(11) -0.0090(10) -0.0087(9) -0.0247(10) C14 0.0324(10) 0.0397(11) 0.0364(11) -0.0084(9) -0.0119(9) -0.0135(9) C15 0.0420(14) 0.117(3) 0.0579(17) 0.0005(16) -0.0247(13) -0.0432(16) C16 0.0247(9) 0.0445(12) 0.0358(11) -0.0074(9) -0.0139(8) -0.0105(8) C17 0.0392(12) 0.0495(13) 0.0422(12) -0.0031(10) -0.0166(10) -0.0217(10) C18 0.0614(16) 0.0555(15) 0.0563(16) 0.0021(12) -0.0249(13) -0.0344(13) C19 0.0630(17) 0.0555(16) 0.0648(17) -0.0037(13) -0.0290(14) -0.0311(14) C20 0.0504(14) 0.0549(15) 0.0562(15) -0.0178(12) -0.0239(12) -0.0168(12) C21 0.0363(11) 0.0506(13) 0.0383(12) -0.0085(10) -0.0161(10) -0.0123(10) C22 0.0398(11) 0.0439(11) 0.0206(9) 0.0043(8) -0.0162(8) -0.0207(9) C23 0.0420(11) 0.0424(12) 0.0285(10) 0.0025(8) -0.0171(9) -0.0218(10) C24 0.0399(11) 0.0492(13) 0.0276(10) 0.0051(9) -0.0145(9) -0.0261(10) C25 0.0604(16) 0.0589(16) 0.0297(12) -0.0032(11) -0.0100(11) -0.0168(13) C26 0.0314(10) 0.0380(11) 0.0275(10) 0.0027(8) -0.0155(8) -0.0134(8) C27 0.0574(16) 0.108(2) 0.0429(14) 0.0063(14) -0.0236(12) -0.0570(17) _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 C12 1.368(3) . ? O1 C15 1.436(4) . ? O2 C23 1.256(3) . ? O3 C24 1.208(3) . ? O4 C24 1.333(3) . ? O4 C25 1.439(3) . ? O5 C26 1.353(3) . ? O5 C27 1.444(3) . ? O6 C26 1.222(2) . ? N1 C2 1.375(3) . ? N1 C9 1.439(2) . ? N1 C1 1.450(2) . ? N2 C8 1.298(3) . ? N2 C22 1.443(2) . ? N2 C1 1.507(3) . ? C1 C16 1.517(3) . ? C2 C3 1.407(3) . ? C2 C7 1.416(3) . ? C3 C4 1.371(3) . ? C4 C5 1.399(3) . ? C5 C6 1.374(3) . ? C6 C7 1.406(3) . ? C7 C8 1.422(3) . ? C9 C14 1.380(3) . ? C9 C10 1.407(3) . ? C10 C11 1.388(3) . ? C11 C12 1.395(4) . ? C12 C13 1.390(4) . ? C13 C14 1.394(3) . ? C16 C17 1.388(3) . ? C16 C21 1.395(3) . ? C17 C18 1.383(4) . ? C18 C19 1.374(4) . ? C19 C20 1.364(4) . ? C20 C21 1.397(4) . ? C22 C23 1.391(3) . ? C22 C26 1.435(3) . ? C23 C24 1.523(3) . ? 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 C12 O1 C15 116.5(2) . . ? C24 O4 C25 115.68(18) . . ? C26 O5 C27 115.20(17) . . ? C2 N1 C9 122.55(16) . . ? C2 N1 C1 119.45(16) . . ? C9 N1 C1 117.25(16) . . ? C8 N2 C22 123.30(17) . . ? C8 N2 C1 119.54(16) . . ? C22 N2 C1 116.91(16) . . ? N1 C1 N2 108.53(16) . . ? N1 C1 C16 114.45(17) . . ? N2 C1 C16 109.51(16) . . ? N1 C2 C3 123.13(19) . . ? N1 C2 C7 118.41(17) . . ? C3 C2 C7 118.42(19) . . ? C4 C3 C2 119.7(2) . . ? C3 C4 C5 122.12(19) . . ? C6 C5 C4 119.2(2) . . ? C5 C6 C7 120.1(2) . . ? C6 C7 C2 120.43(18) . . ? C6 C7 C8 121.37(19) . . ? C2 C7 C8 117.51(18) . . ? N2 C8 C7 121.90(19) . . ? C14 C9 C10 119.83(19) . . ? C14 C9 N1 118.75(19) . . ? C10 C9 N1 121.34(18) . . ? C11 C10 C9 120.1(2) . . ? C10 C11 C12 119.3(2) . . ? O1 C12 C13 123.8(2) . . ? O1 C12 C11 115.5(2) . . ? C13 C12 C11 120.6(2) . . ? C12 C13 C14 119.6(2) . . ? C9 C14 C13 120.3(2) . . ? C17 C16 C21 118.4(2) . . ? C17 C16 C1 122.17(19) . . ? C21 C16 C1 119.4(2) . . ? C18 C17 C16 120.6(2) . . ? C19 C18 C17 120.5(3) . . ? C20 C19 C18 120.0(3) . . ? C19 C20 C21 120.3(2) . . ? C16 C21 C20 120.2(2) . . ? C23 C22 C26 122.91(18) . . ? C23 C22 N2 116.11(17) . . ? C26 C22 N2 120.75(17) . . ? O2 C23 C22 126.07(19) . . ? O2 C23 C24 115.09(19) . . ? C22 C23 C24 118.82(18) . . ? O3 C24 O4 125.30(19) . . ? O3 C24 C23 124.6(2) . . ? O4 C24 C23 109.83(18) . . ? O6 C26 O5 122.10(18) . . ? O6 C26 C22 124.31(19) . . ? O5 C26 C22 113.58(17) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.672 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.087 data_tomas1 _database_code_depnum_ccdc_archive 'CCDC 282677' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H38 N2 O17' _chemical_formula_weight 806.71 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 11.1011(12) _cell_length_b 21.952(2) _cell_length_c 15.9307(17) _cell_angle_alpha 90.00 _cell_angle_beta 103.285(2) _cell_angle_gamma 90.00 _cell_volume 3778.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3096 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 23.3 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.824622 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 1000 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 18415 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6642 _reflns_number_gt 4048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+1.1219P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6642 _refine_ls_number_parameters 523 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1226 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 C1 C 0.9494(2) 0.05938(13) 0.18671(17) 0.0226(6) Uani 1 1 d . . . C2 C 1.0048(2) 0.04470(14) 0.11977(18) 0.0283(7) Uani 1 1 d . . . H2 H 0.9959 0.0717 0.0722 0.034 Uiso 1 1 calc R . . C3 C 1.0725(3) -0.00799(14) 0.12036(19) 0.0326(7) Uani 1 1 d . . . H3 H 1.1099 -0.0173 0.0739 0.039 Uiso 1 1 calc R . . C4 C 1.0849(3) -0.04703(14) 0.18970(19) 0.0342(7) Uani 1 1 d . . . H4 H 1.1303 -0.0838 0.1906 0.041 Uiso 1 1 calc R . . C5 C 1.0320(3) -0.03310(14) 0.25785(19) 0.0319(7) Uani 1 1 d . . . H5 H 1.0424 -0.0603 0.3053 0.038 Uiso 1 1 calc R . . C6 C 0.9635(2) 0.02027(13) 0.25830(17) 0.0245(6) Uani 1 1 d . . . N1 N 0.9126(2) 0.03547(10) 0.32791(14) 0.0270(6) Uani 1 1 d . . . C7 C 0.8987(3) -0.01412(15) 0.3864(2) 0.0455(9) Uani 1 1 d . . . H7A H 0.8625 0.0018 0.4325 0.068 Uiso 1 1 calc R . . H7B H 0.9800 -0.0318 0.4115 0.068 Uiso 1 1 calc R . . H7C H 0.8443 -0.0455 0.3542 0.068 Uiso 1 1 calc R . . C8 C 0.8143(2) 0.08074(12) 0.31439(16) 0.0233(6) Uani 1 1 d . . . H8 H 0.7356 0.0631 0.2793 0.028 Uiso 1 1 calc R . . C9 C 0.7943(2) 0.10574(13) 0.39882(17) 0.0250(7) Uani 1 1 d . . . C10 C 0.8940(3) 0.12777(14) 0.46026(17) 0.0319(7) Uani 1 1 d . . . H10 H 0.9752 0.1248 0.4508 0.038 Uiso 1 1 calc R . . C11 C 0.8759(3) 0.15416(15) 0.53558(18) 0.0382(8) Uani 1 1 d . . . H11 H 0.9447 0.1691 0.5775 0.046 Uiso 1 1 calc R . . C12 C 0.7582(3) 0.15873(15) 0.5498(2) 0.0418(8) Uani 1 1 d . . . H12 H 0.7454 0.1771 0.6010 0.050 Uiso 1 1 calc R . . C13 C 0.6603(3) 0.13656(16) 0.4893(2) 0.0443(9) Uani 1 1 d . . . H13 H 0.5792 0.1394 0.4989 0.053 Uiso 1 1 calc R . . C14 C 0.6776(3) 0.10983(15) 0.41369(19) 0.0366(8) Uani 1 1 d . . . H14 H 0.6086 0.0944 0.3724 0.044 Uiso 1 1 calc R . . N2 N 0.85546(19) 0.13296(10) 0.26802(13) 0.0225(5) Uani 1 1 d . . . O1 O 0.74908(16) 0.17391(8) 0.24773(11) 0.0235(4) Uani 1 1 d . . . C15 C 0.8750(2) 0.11684(13) 0.18243(16) 0.0216(6) Uani 1 1 d . . . H15 H 0.9231 0.1505 0.1633 0.026 Uiso 1 1 calc R . . C16 C 0.7423(2) 0.11625(12) 0.12114(16) 0.0203(6) Uani 1 1 d . . . C17 C 0.7015(2) 0.05960(13) 0.06919(18) 0.0250(7) Uani 1 1 d . . . O2 O 0.6794(2) 0.05759(10) -0.00805(13) 0.0439(6) Uani 1 1 d . . . O3 O 0.70262(16) 0.01226(8) 0.12093(11) 0.0271(5) Uani 1 1 d . . . C18 C 0.6751(3) -0.04599(13) 0.0797(2) 0.0424(8) Uani 1 1 d . . . H18A H 0.6798 -0.0777 0.1237 0.064 Uiso 1 1 calc R . . H18B H 0.7353 -0.0548 0.0449 0.064 Uiso 1 1 calc R . . H18C H 0.5916 -0.0452 0.0424 0.064 Uiso 1 1 calc R . . C19 C 0.6684(2) 0.15235(12) 0.17009(16) 0.0210(6) Uani 1 1 d . . . C20 C 0.5383(3) 0.14004(14) 0.18071(18) 0.0271(7) Uani 1 1 d . . . O4 O 0.47423(19) 0.17769(11) 0.20153(16) 0.0550(7) Uani 1 1 d . . . O5 O 0.50875(17) 0.08162(9) 0.16895(14) 0.0375(5) Uani 1 1 d . . . C21 C 0.3829(3) 0.06723(16) 0.1719(2) 0.0513(10) Uani 1 1 d . . . H21A H 0.3687 0.0234 0.1627 0.077 Uiso 1 1 calc R . . H21B H 0.3257 0.0899 0.1266 0.077 Uiso 1 1 calc R . . H21C H 0.3688 0.0786 0.2283 0.077 Uiso 1 1 calc R . . C22 C 0.6935(2) 0.17946(12) 0.08695(16) 0.0211(6) Uani 1 1 d . . . C23 C 0.5790(3) 0.18154(13) 0.01413(17) 0.0246(6) Uani 1 1 d . . . O6 O 0.48860(19) 0.15170(10) 0.01180(13) 0.0426(6) Uani 1 1 d . . . O7 O 0.59049(16) 0.22322(9) -0.04404(11) 0.0323(5) Uani 1 1 d . . . C24 C 0.4800(3) 0.23266(15) -0.11311(18) 0.0359(8) Uani 1 1 d . . . H24A H 0.4969 0.2639 -0.1529 0.054 Uiso 1 1 calc R . . H24B H 0.4115 0.2460 -0.0883 0.054 Uiso 1 1 calc R . . H24C H 0.4576 0.1944 -0.1445 0.054 Uiso 1 1 calc R . . C25 C 0.7809(2) 0.23087(12) 0.08844(15) 0.0201(6) Uani 1 1 d . . . C26 C 0.8810(2) 0.23320(13) 0.03339(17) 0.0239(6) Uani 1 1 d . . . O8 O 0.92334(17) 0.17729(9) 0.01573(11) 0.0281(5) Uani 1 1 d . . . C27 C 1.0303(3) 0.17989(14) -0.02198(18) 0.0342(7) Uani 1 1 d . . . H27A H 1.0557 0.1384 -0.0328 0.051 Uiso 1 1 calc R . . H27B H 1.0984 0.2006 0.0179 0.051 Uiso 1 1 calc R . . H27C H 1.0090 0.2024 -0.0765 0.051 Uiso 1 1 calc R . . O9 O 0.97568(15) 0.26877(8) 0.09093(11) 0.0248(4) Uani 1 1 d . . . C28 C 0.8366(2) 0.28055(13) -0.03925(16) 0.0227(6) Uani 1 1 d . . . C29 C 0.7875(2) 0.26648(14) -0.13165(17) 0.0253(7) Uani 1 1 d . . . O10 O 0.79800(18) 0.21785(10) -0.16417(12) 0.0362(5) Uani 1 1 d . . . O11 O 0.73214(17) 0.31496(9) -0.17382(11) 0.0316(5) Uani 1 1 d . . . C30 C 0.6838(3) 0.30636(15) -0.26546(17) 0.0381(8) Uani 1 1 d . . . H30A H 0.6452 0.3442 -0.2910 0.057 Uiso 1 1 calc R . . H30B H 0.6220 0.2737 -0.2748 0.057 Uiso 1 1 calc R . . H30C H 0.7516 0.2953 -0.2926 0.057 Uiso 1 1 calc R . . C31 C 0.8429(2) 0.33368(13) 0.00111(17) 0.0233(6) Uani 1 1 d . . . C32 C 0.7924(3) 0.39462(13) -0.02973(17) 0.0261(7) Uani 1 1 d . . . O12 O 0.69478(19) 0.41209(10) -0.01979(13) 0.0392(5) Uani 1 1 d . . . O13 O 0.86798(17) 0.42516(9) -0.06778(12) 0.0332(5) Uani 1 1 d . . . C33 C 0.8272(3) 0.48648(15) -0.0944(2) 0.0562(10) Uani 1 1 d . . . H33A H 0.8882 0.5061 -0.1213 0.084 Uiso 1 1 calc R . . H33B H 0.8186 0.5101 -0.0439 0.084 Uiso 1 1 calc R . . H33C H 0.7471 0.4847 -0.1360 0.084 Uiso 1 1 calc R . . C34 C 0.8949(2) 0.31916(13) 0.09800(16) 0.0231(6) Uani 1 1 d . . . C35 C 0.9595(2) 0.37054(14) 0.15397(18) 0.0276(7) Uani 1 1 d . . . O14 O 0.93702(19) 0.42301(10) 0.13654(13) 0.0396(5) Uani 1 1 d . . . O15 O 1.04032(17) 0.34951(9) 0.22164(12) 0.0320(5) Uani 1 1 d . . . C36 C 1.0951(3) 0.39544(15) 0.2843(2) 0.0402(8) Uani 1 1 d . . . H36A H 1.1540 0.3761 0.3322 0.060 Uiso 1 1 calc R . . H36B H 1.0298 0.4156 0.3064 0.060 Uiso 1 1 calc R . . H36C H 1.1383 0.4257 0.2568 0.060 Uiso 1 1 calc R . . C37 C 0.7909(2) 0.28471(13) 0.12836(16) 0.0218(6) Uani 1 1 d . . . C38 C 0.7290(2) 0.31116(13) 0.19261(17) 0.0235(6) Uani 1 1 d . . . O16 O 0.77579(18) 0.35137(10) 0.24117(12) 0.0385(5) Uani 1 1 d . . . O17 O 0.62027(16) 0.28557(9) 0.19074(11) 0.0276(5) Uani 1 1 d . . . C39 C 0.5650(3) 0.30198(15) 0.26145(19) 0.0394(8) Uani 1 1 d . . . H39A H 0.4855 0.2809 0.2550 0.059 Uiso 1 1 calc R . . H39B H 0.5516 0.3461 0.2611 0.059 Uiso 1 1 calc R . . H39C H 0.6204 0.2900 0.3161 0.059 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0204(14) 0.0209(16) 0.0261(15) -0.0017(13) 0.0048(12) -0.0022(12) C2 0.0270(15) 0.0297(18) 0.0290(16) -0.0012(14) 0.0077(13) -0.0005(14) C3 0.0295(16) 0.0329(19) 0.0379(18) -0.0055(15) 0.0127(14) -0.0004(15) C4 0.0271(16) 0.0293(18) 0.0461(19) -0.0066(16) 0.0085(14) 0.0043(14) C5 0.0321(16) 0.0275(18) 0.0350(17) 0.0017(14) 0.0056(14) 0.0036(15) C6 0.0243(15) 0.0237(17) 0.0236(15) -0.0016(13) 0.0015(12) 0.0010(13) N1 0.0334(13) 0.0214(13) 0.0267(13) 0.0037(11) 0.0077(10) 0.0051(11) C7 0.069(2) 0.033(2) 0.0391(19) 0.0132(16) 0.0223(17) 0.0133(18) C8 0.0253(15) 0.0205(15) 0.0241(15) 0.0015(12) 0.0056(12) -0.0022(13) C9 0.0300(16) 0.0208(16) 0.0248(15) 0.0066(13) 0.0077(12) 0.0037(13) C10 0.0309(16) 0.0382(19) 0.0263(16) 0.0001(14) 0.0060(13) 0.0005(15) C11 0.0444(19) 0.044(2) 0.0252(17) -0.0067(15) 0.0055(14) -0.0038(17) C12 0.056(2) 0.043(2) 0.0306(18) -0.0045(16) 0.0191(16) 0.0068(18) C13 0.0356(18) 0.063(3) 0.0381(19) -0.0018(18) 0.0161(15) 0.0077(18) C14 0.0329(17) 0.046(2) 0.0314(17) -0.0007(16) 0.0088(13) -0.0030(16) N2 0.0230(12) 0.0222(13) 0.0224(12) 0.0018(10) 0.0055(10) 0.0030(11) O1 0.0260(10) 0.0203(10) 0.0238(10) -0.0018(8) 0.0048(8) 0.0025(9) C15 0.0226(14) 0.0222(16) 0.0210(14) -0.0003(12) 0.0070(11) -0.0043(12) C16 0.0208(14) 0.0194(15) 0.0208(14) 0.0001(12) 0.0046(11) -0.0016(12) C17 0.0242(15) 0.0225(17) 0.0278(17) -0.0014(14) 0.0048(12) 0.0008(13) O2 0.0725(16) 0.0286(13) 0.0259(12) -0.0022(10) 0.0015(10) -0.0015(12) O3 0.0344(11) 0.0165(11) 0.0298(11) -0.0005(9) 0.0064(9) -0.0037(9) C18 0.061(2) 0.0167(17) 0.048(2) -0.0037(15) 0.0081(17) -0.0034(16) C19 0.0229(14) 0.0182(15) 0.0222(14) -0.0009(12) 0.0058(11) -0.0039(12) C20 0.0268(16) 0.0248(18) 0.0306(16) -0.0004(14) 0.0083(13) -0.0013(14) O4 0.0360(13) 0.0372(14) 0.101(2) -0.0241(14) 0.0338(13) -0.0057(12) O5 0.0290(11) 0.0222(12) 0.0648(15) 0.0063(11) 0.0180(10) -0.0051(10) C21 0.0331(18) 0.034(2) 0.092(3) 0.0051(19) 0.0261(19) -0.0090(16) C22 0.0219(14) 0.0200(15) 0.0206(14) 0.0004(12) 0.0036(11) -0.0015(12) C23 0.0308(16) 0.0172(16) 0.0256(16) 0.0006(13) 0.0059(13) 0.0020(14) O6 0.0361(12) 0.0406(14) 0.0430(13) 0.0104(11) -0.0074(10) -0.0195(11) O7 0.0312(11) 0.0378(13) 0.0249(11) 0.0090(10) 0.0001(8) -0.0046(10) C24 0.0323(17) 0.041(2) 0.0291(17) 0.0077(15) -0.0031(13) 0.0066(15) C25 0.0215(14) 0.0217(16) 0.0163(13) 0.0052(12) 0.0027(11) 0.0001(12) C26 0.0278(15) 0.0212(16) 0.0236(15) -0.0003(13) 0.0076(12) -0.0046(13) O8 0.0350(11) 0.0218(11) 0.0322(11) 0.0008(9) 0.0171(9) 0.0031(9) C27 0.0395(17) 0.0334(19) 0.0361(18) 0.0020(15) 0.0221(14) 0.0058(15) O9 0.0251(10) 0.0214(11) 0.0280(10) 0.0007(9) 0.0063(8) -0.0003(9) C28 0.0242(15) 0.0223(16) 0.0234(15) -0.0011(13) 0.0089(12) -0.0034(13) C29 0.0265(15) 0.0264(18) 0.0250(16) 0.0008(14) 0.0103(12) -0.0038(14) O10 0.0473(13) 0.0318(13) 0.0298(11) -0.0031(10) 0.0093(10) -0.0004(11) O11 0.0358(11) 0.0320(12) 0.0240(11) 0.0027(9) 0.0006(9) 0.0008(10) C30 0.0363(17) 0.050(2) 0.0245(16) 0.0017(15) -0.0002(13) -0.0016(16) C31 0.0226(14) 0.0231(16) 0.0260(15) 0.0049(13) 0.0092(12) -0.0046(13) C32 0.0273(16) 0.0250(17) 0.0254(15) -0.0034(13) 0.0047(12) -0.0040(14) O12 0.0338(12) 0.0359(14) 0.0498(14) -0.0032(11) 0.0137(10) 0.0052(11) O13 0.0370(12) 0.0250(12) 0.0395(12) 0.0105(9) 0.0128(10) -0.0035(10) C33 0.077(3) 0.030(2) 0.063(2) 0.0212(18) 0.020(2) 0.009(2) C34 0.0253(14) 0.0213(16) 0.0238(15) -0.0004(12) 0.0078(12) 0.0004(13) C35 0.0264(16) 0.0283(19) 0.0287(16) -0.0003(14) 0.0079(13) -0.0059(14) O14 0.0552(14) 0.0206(13) 0.0398(13) 0.0003(10) 0.0042(10) -0.0070(11) O15 0.0331(11) 0.0272(12) 0.0309(11) -0.0041(9) -0.0027(9) -0.0062(10) C36 0.0383(18) 0.036(2) 0.0400(19) -0.0071(16) -0.0036(15) -0.0091(16) C37 0.0244(14) 0.0200(16) 0.0202(14) 0.0011(12) 0.0039(11) 0.0016(13) C38 0.0264(15) 0.0216(16) 0.0220(15) 0.0038(13) 0.0043(12) 0.0050(13) O16 0.0414(12) 0.0369(13) 0.0380(12) -0.0165(11) 0.0109(10) -0.0063(11) O17 0.0313(11) 0.0243(11) 0.0306(11) -0.0012(9) 0.0142(9) -0.0019(9) C39 0.050(2) 0.034(2) 0.0446(19) -0.0015(15) 0.0325(16) 0.0010(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.386(4) . ? C1 C6 1.407(4) . ? C1 C15 1.501(4) . ? C2 C3 1.378(4) . ? C3 C4 1.380(4) . ? C4 C5 1.382(4) . ? C5 C6 1.398(4) . ? C6 N1 1.396(3) . ? N1 C8 1.455(3) . ? N1 C7 1.464(4) . ? C8 N2 1.491(3) . ? C8 C9 1.516(4) . ? C9 C14 1.372(4) . ? C9 C10 1.386(4) . ? C10 C11 1.388(4) . ? C11 C12 1.379(4) . ? C12 C13 1.366(4) . ? C13 C14 1.392(4) . ? N2 O1 1.460(3) . ? N2 C15 1.472(3) . ? O1 C19 1.431(3) . ? C15 C16 1.569(3) . ? C16 C19 1.484(4) . ? C16 C17 1.505(4) . ? C16 C22 1.543(4) . ? C17 O2 1.199(3) . ? C17 O3 1.325(3) . ? O3 C18 1.438(3) . ? C19 C20 1.516(4) . ? C19 C22 1.535(3) . ? C20 O4 1.187(3) . ? C20 O5 1.326(3) . ? O5 C21 1.444(3) . ? C22 C25 1.484(4) . ? C22 C23 1.512(4) . ? C23 O6 1.192(3) . ? C23 O7 1.329(3) . ? O7 C24 1.462(3) . ? C25 C37 1.335(4) . ? C25 C26 1.567(4) . ? C26 O8 1.366(3) . ? C26 O9 1.453(3) . ? C26 C28 1.549(4) . ? O8 C27 1.449(3) . ? O9 C34 1.444(3) . ? C28 C31 1.326(4) . ? C28 C29 1.480(4) . ? C29 O10 1.204(3) . ? C29 O11 1.331(3) . ? O11 C30 1.447(3) . ? C31 C32 1.490(4) . ? C31 C34 1.552(4) . ? C32 O12 1.194(3) . ? C32 O13 1.325(3) . ? O13 C33 1.452(4) . ? C34 C35 1.512(4) . ? C34 C37 1.548(4) . ? C35 O14 1.198(3) . ? C35 O15 1.317(3) . ? O15 C36 1.451(3) . ? C37 C38 1.477(4) . ? C38 O16 1.209(3) . ? C38 O17 1.325(3) . ? O17 C39 1.447(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.7(3) . . ? C2 C1 C15 119.8(2) . . ? C6 C1 C15 120.5(2) . . ? C3 C2 C1 121.8(3) . . ? C2 C3 C4 118.7(3) . . ? C3 C4 C5 120.6(3) . . ? C4 C5 C6 121.3(3) . . ? N1 C6 C5 121.6(3) . . ? N1 C6 C1 120.5(2) . . ? C5 C6 C1 117.8(3) . . ? C6 N1 C8 118.2(2) . . ? C6 N1 C7 116.7(2) . . ? C8 N1 C7 114.6(2) . . ? N1 C8 N2 107.1(2) . . ? N1 C8 C9 112.0(2) . . ? N2 C8 C9 106.6(2) . . ? C14 C9 C10 119.2(3) . . ? C14 C9 C8 120.9(2) . . ? C10 C9 C8 119.8(2) . . ? C9 C10 C11 120.3(3) . . ? C12 C11 C10 120.2(3) . . ? C13 C12 C11 119.2(3) . . ? C12 C13 C14 121.0(3) . . ? C9 C14 C13 120.0(3) . . ? O1 N2 C15 103.10(17) . . ? O1 N2 C8 104.99(18) . . ? C15 N2 C8 113.7(2) . . ? C19 O1 N2 107.56(17) . . ? N2 C15 C1 110.9(2) . . ? N2 C15 C16 105.2(2) . . ? C1 C15 C16 116.7(2) . . ? C19 C16 C17 126.7(2) . . ? C19 C16 C22 60.91(17) . . ? C17 C16 C22 120.8(2) . . ? C19 C16 C15 102.8(2) . . ? C17 C16 C15 118.0(2) . . ? C22 C16 C15 114.5(2) . . ? O2 C17 O3 125.5(3) . . ? O2 C17 C16 124.0(3) . . ? O3 C17 C16 110.3(2) . . ? C17 O3 C18 116.3(2) . . ? O1 C19 C16 108.6(2) . . ? O1 C19 C20 112.7(2) . . ? C16 C19 C20 128.2(2) . . ? O1 C19 C22 114.6(2) . . ? C16 C19 C22 61.43(17) . . ? C20 C19 C22 122.1(2) . . ? O4 C20 O5 124.6(3) . . ? O4 C20 C19 123.7(3) . . ? O5 C20 C19 111.6(2) . . ? C20 O5 C21 114.7(2) . . ? C25 C22 C23 114.9(2) . . ? C25 C22 C19 121.9(2) . . ? C23 C22 C19 112.7(2) . . ? C25 C22 C16 120.2(2) . . ? C23 C22 C16 117.6(2) . . ? C19 C22 C16 57.67(17) . . ? O6 C23 O7 124.9(2) . . ? O6 C23 C22 124.1(2) . . ? O7 C23 C22 110.9(2) . . ? C23 O7 C24 115.1(2) . . ? C37 C25 C22 131.6(2) . . ? C37 C25 C26 104.2(2) . . ? C22 C25 C26 124.1(2) . . ? O8 C26 O9 112.3(2) . . ? O8 C26 C28 121.0(2) . . ? O9 C26 C28 99.8(2) . . ? O8 C26 C25 114.0(2) . . ? O9 C26 C25 99.65(19) . . ? C28 C26 C25 107.2(2) . . ? C26 O8 C27 113.8(2) . . ? C34 O9 C26 95.10(18) . . ? C31 C28 C29 129.2(3) . . ? C31 C28 C26 104.8(2) . . ? C29 C28 C26 125.7(2) . . ? O10 C29 O11 124.8(3) . . ? O10 C29 C28 124.3(3) . . ? O11 C29 C28 110.9(2) . . ? C29 O11 C30 115.2(2) . . ? C28 C31 C32 131.0(2) . . ? C28 C31 C34 105.5(2) . . ? C32 C31 C34 122.6(2) . . ? O12 C32 O13 126.0(3) . . ? O12 C32 C31 121.9(3) . . ? O13 C32 C31 112.1(2) . . ? C32 O13 C33 114.5(2) . . ? O9 C34 C35 113.5(2) . . ? O9 C34 C37 99.8(2) . . ? C35 C34 C37 117.8(2) . . ? O9 C34 C31 100.1(2) . . ? C35 C34 C31 116.8(2) . . ? C37 C34 C31 106.1(2) . . ? O14 C35 O15 126.4(3) . . ? O14 C35 C34 122.4(3) . . ? O15 C35 C34 111.3(3) . . ? C35 O15 C36 114.7(2) . . ? C25 C37 C38 132.6(3) . . ? C25 C37 C34 105.7(2) . . ? C38 C37 C34 121.6(2) . . ? O16 C38 O17 125.4(3) . . ? O16 C38 C37 122.0(3) . . ? O17 C38 C37 112.6(2) . . ? C38 O17 C39 115.1(2) . . ? 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 C6 C1 C2 C3 1.0(4) . . . . ? C15 C1 C2 C3 -179.1(2) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C3 C4 C5 C6 0.7(4) . . . . ? C4 C5 C6 N1 -178.2(2) . . . . ? C4 C5 C6 C1 0.4(4) . . . . ? C2 C1 C6 N1 177.4(2) . . . . ? C15 C1 C6 N1 -2.5(4) . . . . ? C2 C1 C6 C5 -1.2(4) . . . . ? C15 C1 C6 C5 178.9(2) . . . . ? C5 C6 N1 C8 -162.2(2) . . . . ? C1 C6 N1 C8 19.3(4) . . . . ? C5 C6 N1 C7 -19.2(4) . . . . ? C1 C6 N1 C7 162.2(3) . . . . ? C6 N1 C8 N2 -47.0(3) . . . . ? C7 N1 C8 N2 169.3(2) . . . . ? C6 N1 C8 C9 -163.5(2) . . . . ? C7 N1 C8 C9 52.8(3) . . . . ? N1 C8 C9 C14 -132.0(3) . . . . ? N2 C8 C9 C14 111.2(3) . . . . ? N1 C8 C9 C10 51.4(3) . . . . ? N2 C8 C9 C10 -65.4(3) . . . . ? C14 C9 C10 C11 -0.6(4) . . . . ? C8 C9 C10 C11 176.1(3) . . . . ? C9 C10 C11 C12 -0.1(5) . . . . ? C10 C11 C12 C13 0.5(5) . . . . ? C11 C12 C13 C14 -0.3(5) . . . . ? C10 C9 C14 C13 0.8(5) . . . . ? C8 C9 C14 C13 -175.8(3) . . . . ? C12 C13 C14 C9 -0.4(5) . . . . ? N1 C8 N2 O1 174.02(18) . . . . ? C9 C8 N2 O1 -66.0(2) . . . . ? N1 C8 N2 C15 62.1(3) . . . . ? C9 C8 N2 C15 -177.9(2) . . . . ? C15 N2 O1 C19 35.9(2) . . . . ? C8 N2 O1 C19 -83.4(2) . . . . ? O1 N2 C15 C1 -160.07(19) . . . . ? C8 N2 C15 C1 -47.0(3) . . . . ? O1 N2 C15 C16 -33.1(2) . . . . ? C8 N2 C15 C16 80.0(2) . . . . ? C2 C1 C15 N2 -163.5(2) . . . . ? C6 C1 C15 N2 16.4(3) . . . . ? C2 C1 C15 C16 76.2(3) . . . . ? C6 C1 C15 C16 -103.9(3) . . . . ? N2 C15 C16 C19 19.0(3) . . . . ? C1 C15 C16 C19 142.4(2) . . . . ? N2 C15 C16 C17 -125.6(2) . . . . ? C1 C15 C16 C17 -2.2(3) . . . . ? N2 C15 C16 C22 82.7(3) . . . . ? C1 C15 C16 C22 -154.0(2) . . . . ? C19 C16 C17 O2 109.0(3) . . . . ? C22 C16 C17 O2 34.2(4) . . . . ? C15 C16 C17 O2 -115.7(3) . . . . ? C19 C16 C17 O3 -75.5(3) . . . . ? C22 C16 C17 O3 -150.3(2) . . . . ? C15 C16 C17 O3 59.8(3) . . . . ? O2 C17 O3 C18 0.2(4) . . . . ? C16 C17 O3 C18 -175.2(2) . . . . ? N2 O1 C19 C16 -24.0(3) . . . . ? N2 O1 C19 C20 124.0(2) . . . . ? N2 O1 C19 C22 -90.4(2) . . . . ? C17 C16 C19 O1 143.1(2) . . . . ? C22 C16 C19 O1 -108.5(2) . . . . ? C15 C16 C19 O1 2.7(3) . . . . ? C17 C16 C19 C20 1.5(4) . . . . ? C22 C16 C19 C20 110.0(3) . . . . ? C15 C16 C19 C20 -138.8(3) . . . . ? C17 C16 C19 C22 -108.5(3) . . . . ? C15 C16 C19 C22 111.2(2) . . . . ? O1 C19 C20 O4 59.5(4) . . . . ? C16 C19 C20 O4 -160.2(3) . . . . ? C22 C19 C20 O4 -83.1(4) . . . . ? O1 C19 C20 O5 -116.7(2) . . . . ? C16 C19 C20 O5 23.6(4) . . . . ? C22 C19 C20 O5 100.6(3) . . . . ? O4 C20 O5 C21 8.1(4) . . . . ? C19 C20 O5 C21 -175.7(2) . . . . ? O1 C19 C22 C25 -9.3(3) . . . . ? C16 C19 C22 C25 -107.9(3) . . . . ? C20 C19 C22 C25 132.7(3) . . . . ? O1 C19 C22 C23 -152.1(2) . . . . ? C16 C19 C22 C23 109.2(2) . . . . ? C20 C19 C22 C23 -10.1(4) . . . . ? O1 C19 C22 C16 98.6(2) . . . . ? C20 C19 C22 C16 -119.4(3) . . . . ? C19 C16 C22 C25 110.8(3) . . . . ? C17 C16 C22 C25 -131.5(3) . . . . ? C15 C16 C22 C25 19.4(3) . . . . ? C19 C16 C22 C23 -100.7(2) . . . . ? C17 C16 C22 C23 17.0(3) . . . . ? C15 C16 C22 C23 167.9(2) . . . . ? C17 C16 C22 C19 117.7(3) . . . . ? C15 C16 C22 C19 -91.4(2) . . . . ? C25 C22 C23 O6 -164.8(3) . . . . ? C19 C22 C23 O6 -19.1(4) . . . . ? C16 C22 C23 O6 45.1(4) . . . . ? C25 C22 C23 O7 11.9(3) . . . . ? C19 C22 C23 O7 157.5(2) . . . . ? C16 C22 C23 O7 -138.3(2) . . . . ? O6 C23 O7 C24 2.0(4) . . . . ? C22 C23 O7 C24 -174.6(2) . . . . ? C23 C22 C25 C37 92.0(3) . . . . ? C19 C22 C25 C37 -50.2(4) . . . . ? C16 C22 C25 C37 -118.7(3) . . . . ? C23 C22 C25 C26 -83.4(3) . . . . ? C19 C22 C25 C26 134.4(3) . . . . ? C16 C22 C25 C26 66.0(3) . . . . ? C37 C25 C26 O8 154.4(2) . . . . ? C22 C25 C26 O8 -29.2(3) . . . . ? C37 C25 C26 O9 34.6(2) . . . . ? C22 C25 C26 O9 -149.0(2) . . . . ? C37 C25 C26 C28 -68.9(3) . . . . ? C22 C25 C26 C28 107.5(3) . . . . ? O9 C26 O8 C27 -57.5(3) . . . . ? C28 C26 O8 C27 60.0(3) . . . . ? C25 C26 O8 C27 -169.9(2) . . . . ? O8 C26 O9 C34 -175.9(2) . . . . ? C28 C26 O9 C34 54.7(2) . . . . ? C25 C26 O9 C34 -54.8(2) . . . . ? O8 C26 C28 C31 -159.4(2) . . . . ? O9 C26 C28 C31 -35.9(3) . . . . ? C25 C26 C28 C31 67.5(3) . . . . ? O8 C26 C28 C29 25.7(4) . . . . ? O9 C26 C28 C29 149.3(2) . . . . ? C25 C26 C28 C29 -107.3(3) . . . . ? C31 C28 C29 O10 171.5(3) . . . . ? C26 C28 C29 O10 -14.9(4) . . . . ? C31 C28 C29 O11 -7.6(4) . . . . ? C26 C28 C29 O11 166.0(2) . . . . ? O10 C29 O11 C30 -0.7(4) . . . . ? C28 C29 O11 C30 178.4(2) . . . . ? C29 C28 C31 C32 7.1(5) . . . . ? C26 C28 C31 C32 -167.5(3) . . . . ? C29 C28 C31 C34 176.3(2) . . . . ? C26 C28 C31 C34 1.7(3) . . . . ? C28 C31 C32 O12 94.6(4) . . . . ? C34 C31 C32 O12 -73.0(4) . . . . ? C28 C31 C32 O13 -85.5(4) . . . . ? C34 C31 C32 O13 106.9(3) . . . . ? O12 C32 O13 C33 3.5(4) . . . . ? C31 C32 O13 C33 -176.4(2) . . . . ? C26 O9 C34 C35 -178.8(2) . . . . ? C26 O9 C34 C37 54.9(2) . . . . ? C26 O9 C34 C31 -53.5(2) . . . . ? C28 C31 C34 O9 33.1(3) . . . . ? C32 C31 C34 O9 -156.5(2) . . . . ? C28 C31 C34 C35 156.1(2) . . . . ? C32 C31 C34 C35 -33.5(3) . . . . ? C28 C31 C34 C37 -70.3(3) . . . . ? C32 C31 C34 C37 100.1(3) . . . . ? O9 C34 C35 O14 141.4(3) . . . . ? C37 C34 C35 O14 -102.5(3) . . . . ? C31 C34 C35 O14 25.6(4) . . . . ? O9 C34 C35 O15 -38.7(3) . . . . ? C37 C34 C35 O15 77.5(3) . . . . ? C31 C34 C35 O15 -154.4(2) . . . . ? O14 C35 O15 C36 7.4(4) . . . . ? C34 C35 O15 C36 -172.6(2) . . . . ? C22 C25 C37 C38 7.4(5) . . . . ? C26 C25 C37 C38 -176.5(3) . . . . ? C22 C25 C37 C34 -175.9(3) . . . . ? C26 C25 C37 C34 0.1(3) . . . . ? O9 C34 C37 C25 -35.1(2) . . . . ? C35 C34 C37 C25 -158.4(2) . . . . ? C31 C34 C37 C25 68.6(3) . . . . ? O9 C34 C37 C38 142.0(2) . . . . ? C35 C34 C37 C38 18.7(4) . . . . ? C31 C34 C37 C38 -114.3(3) . . . . ? C25 C37 C38 O16 155.7(3) . . . . ? C34 C37 C38 O16 -20.5(4) . . . . ? C25 C37 C38 O17 -23.6(4) . . . . ? C34 C37 C38 O17 160.1(2) . . . . ? O16 C38 O17 C39 -9.5(4) . . . . ? C37 C38 O17 C39 169.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.267 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.052