data_global _journal_coden_Cambridge ? loop_ _publ_author_name 'Troels Koch' 'Signe Christensen' 'Lotte-Emilie Larsen' 'Daniel Sejer Pedersen' 'Christoph Rosenbolm' 'Mads Sorensen' 'Jesper Wengel' _publ_contact_author_name 'Dr Troels Koch' _publ_contact_author_address ; Chemistry Cureon A/S Fruebjergvej 3 Copenhagen 2100 DENMARK ; # Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2002 _publ_contact_author_email TK@CUREON.COM _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthesis of 2'-Amino-LNA: A New Strategy ; data_sw0208 _database_code_CSD 198987 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H28 N8 O7' _chemical_formula_sum 'C32 H28 N8 O7' _chemical_formula_weight 636.62 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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.6880(2) _cell_length_b 13.2934(3) _cell_length_c 31.1120(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3179.64(14) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7434 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 21.49 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.903 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The absolute structure was assigned from the known configuration of the starting material. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7601 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 21.51 _reflns_number_total 3480 _reflns_number_gt 3022 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (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^)+(0.0308P)^2^+1.2911P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(16) _refine_ls_number_reflns 3480 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 -0.5472(4) 0.6484(2) 0.65105(9) 0.0545(8) Uani 1 1 d . . . O2 O -0.0624(3) 0.76077(18) 0.65089(7) 0.0398(6) Uani 1 1 d . . . O3 O -0.1335(3) 1.01240(17) 0.61720(7) 0.0454(7) Uani 1 1 d . . . O4 O 0.1306(3) 0.89621(19) 0.70366(8) 0.0465(7) Uani 1 1 d . . . O5 O 0.3804(4) 0.8252(2) 0.72402(9) 0.0714(9) Uani 1 1 d . . . O6 O 0.1675(3) 0.77845(17) 0.57608(7) 0.0405(6) Uani 1 1 d . . . O7 O -0.0410(4) 0.6671(2) 0.55896(10) 0.0623(8) Uani 1 1 d . . . N1 N -0.3114(4) 0.7119(2) 0.68724(9) 0.0343(7) Uani 1 1 d . . . N2 N -0.5064(4) 0.6123(2) 0.72290(10) 0.0448(8) Uani 1 1 d . . . N3 N -0.6441(5) 0.5480(3) 0.72786(12) 0.0670(10) Uani 1 1 d . . . N4 N -0.6398(6) 0.5230(3) 0.76809(14) 0.0800(12) Uani 1 1 d . . . N5 N -0.5049(5) 0.5674(3) 0.78986(11) 0.0667(11) Uani 1 1 d . . . N6 N -0.3799(4) 0.8664(2) 0.59483(10) 0.0473(9) Uani 1 1 d . . . N7 N -0.4745(5) 0.9379(3) 0.58558(10) 0.0446(8) Uani 1 1 d . . . N8 N -0.5660(5) 0.9979(3) 0.57231(12) 0.0643(11) Uani 1 1 d . . . C1 C -0.4628(5) 0.6573(3) 0.68328(13) 0.0412(10) Uani 1 1 d . . . C2 C -0.4226(5) 0.6234(3) 0.76067(13) 0.0450(11) Uani 1 1 d . . . C3 C -0.2767(5) 0.6868(3) 0.76308(12) 0.0474(11) Uani 1 1 d . . . C4 C -0.2276(5) 0.7284(3) 0.72579(12) 0.0417(10) Uani 1 1 d . . . H4 H -0.1294 0.7718 0.7259 0.050 Uiso 1 1 calc R . . C5 C -0.1884(7) 0.7031(4) 0.80561(13) 0.0790(16) Uani 1 1 d . . . H5A H -0.0892 0.7485 0.8018 0.118 Uiso 1 1 calc R . . H5B H -0.1473 0.6385 0.8169 0.118 Uiso 1 1 calc R . . H5C H -0.2710 0.7330 0.8259 0.118 Uiso 1 1 calc R . . C6 C -0.2457(5) 0.7561(3) 0.64706(12) 0.0384(10) Uani 1 1 d . . . H6 H -0.2784 0.7125 0.6221 0.046 Uiso 1 1 calc R . . C7 C -0.3110(5) 0.8652(2) 0.63941(11) 0.0370(9) Uani 1 1 d . . . H7 H -0.4024 0.8846 0.6607 0.044 Uiso 1 1 calc R . . C8 C -0.1457(5) 0.9288(2) 0.64490(11) 0.0355(9) Uani 1 1 d . . . H8 H -0.1365 0.9519 0.6754 0.043 Uiso 1 1 calc R . . C9 C 0.0025(5) 0.8553(3) 0.63509(11) 0.0360(9) Uani 1 1 d . . . C10 C 0.0353(5) 0.8514(3) 0.58724(11) 0.0418(10) Uani 1 1 d . . . H10A H -0.0743 0.8339 0.5723 0.050 Uiso 1 1 calc R . . H10B H 0.0722 0.9187 0.5772 0.050 Uiso 1 1 calc R . . C11 C -0.2104(6) 1.1031(3) 0.63263(12) 0.0532(12) Uani 1 1 d . . . H11A H -0.1541 1.1243 0.6598 0.064 Uiso 1 1 calc R . . H11B H -0.3359 1.0929 0.6381 0.064 Uiso 1 1 calc R . . C12 C -0.1847(7) 1.1818(3) 0.59859(13) 0.0507(11) Uani 1 1 d . . . C13 C -0.3251(7) 1.2221(3) 0.57851(15) 0.0689(13) Uani 1 1 d . . . H13 H -0.4385 1.2011 0.5866 0.083 Uiso 1 1 calc R . . C14 C -0.3060(8) 1.2923(4) 0.54684(18) 0.0822(16) Uani 1 1 d . . . H14 H -0.4056 1.3200 0.5332 0.099 Uiso 1 1 calc R . . C15 C -0.1430(10) 1.3227(3) 0.53480(15) 0.0808(16) Uani 1 1 d . . . H15 H -0.1303 1.3711 0.5126 0.097 Uiso 1 1 calc R . . C16 C 0.0031(8) 1.2839(4) 0.55445(15) 0.0757(15) Uani 1 1 d . . . H16 H 0.1162 1.3055 0.5463 0.091 Uiso 1 1 calc R . . C17 C -0.0202(7) 1.2116(3) 0.58677(13) 0.0623(13) Uani 1 1 d . . . H17 H 0.0783 1.1831 0.6006 0.075 Uiso 1 1 calc R . . C18 C 0.1712(5) 0.8744(3) 0.65881(11) 0.0466(10) Uani 1 1 d . . . H18A H 0.2472 0.8144 0.6570 0.056 Uiso 1 1 calc R . . H18B H 0.2332 0.9320 0.6457 0.056 Uiso 1 1 calc R . . C19 C 0.2507(6) 0.8719(3) 0.73313(13) 0.0458(11) Uani 1 1 d . . . C20 C 0.2092(5) 0.9087(3) 0.77660(12) 0.0432(10) Uani 1 1 d . . . C21 C 0.0569(6) 0.9618(3) 0.78535(13) 0.0514(11) Uani 1 1 d . . . H21 H -0.0257 0.9729 0.7632 0.062 Uiso 1 1 calc R . . C22 C 0.0258(7) 0.9982(3) 0.82602(14) 0.0630(13) Uani 1 1 d . . . H22 H -0.0787 1.0339 0.8318 0.076 Uiso 1 1 calc R . . C23 C 0.1447(8) 0.9834(3) 0.85839(14) 0.0680(13) Uani 1 1 d . . . H23 H 0.1233 1.0092 0.8864 0.082 Uiso 1 1 calc R . . C24 C 0.2954(7) 0.9305(3) 0.84988(15) 0.0704(14) Uani 1 1 d . . . H24 H 0.3770 0.9195 0.8723 0.084 Uiso 1 1 calc R . . C25 C 0.3291(6) 0.8935(3) 0.80922(14) 0.0606(12) Uani 1 1 d . . . H25 H 0.4339 0.8578 0.8037 0.073 Uiso 1 1 calc R . . C26 C 0.1093(6) 0.6897(3) 0.55949(11) 0.0415(10) Uani 1 1 d . . . C27 C 0.2545(5) 0.6289(3) 0.54149(11) 0.0372(9) Uani 1 1 d . . . C28 C 0.2112(6) 0.5404(3) 0.52020(13) 0.0512(11) Uani 1 1 d . . . H28 H 0.0931 0.5197 0.5187 0.061 Uiso 1 1 calc R . . C29 C 0.3380(8) 0.4829(3) 0.50139(13) 0.0626(13) Uani 1 1 d . . . H29 H 0.3077 0.4228 0.4867 0.075 Uiso 1 1 calc R . . C30 C 0.5084(7) 0.5122(3) 0.50382(13) 0.0583(12) Uani 1 1 d . . . H30 H 0.5959 0.4724 0.4906 0.070 Uiso 1 1 calc R . . C31 C 0.5545(6) 0.5991(3) 0.52537(13) 0.0558(12) Uani 1 1 d . . . H31 H 0.6733 0.6182 0.5274 0.067 Uiso 1 1 calc R . . C32 C 0.4275(5) 0.6575(3) 0.54384(12) 0.0459(11) Uani 1 1 d . . . H32 H 0.4585 0.7178 0.5583 0.055 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 0.0495(18) 0.0653(19) 0.0487(18) 0.0012(15) -0.0064(15) -0.0097(15) O2 0.0324(17) 0.0405(15) 0.0464(15) 0.0118(13) 0.0076(13) 0.0055(13) O3 0.0604(18) 0.0315(13) 0.0443(14) 0.0057(13) 0.0160(14) 0.0111(14) O4 0.0360(17) 0.0600(16) 0.0437(15) -0.0058(13) 0.0022(14) 0.0082(14) O5 0.060(2) 0.087(2) 0.0672(19) -0.0068(17) -0.0067(17) 0.034(2) O6 0.0439(16) 0.0349(14) 0.0428(14) -0.0034(12) 0.0117(13) 0.0011(14) O7 0.0356(19) 0.0601(18) 0.091(2) -0.0102(17) 0.0061(17) -0.0086(16) N1 0.032(2) 0.0358(17) 0.0348(17) 0.0041(14) 0.0016(15) -0.0023(16) N2 0.035(2) 0.0466(19) 0.052(2) 0.0114(18) 0.0068(18) -0.0064(17) N3 0.050(2) 0.083(3) 0.068(3) 0.016(2) 0.008(2) -0.014(2) N4 0.067(3) 0.097(3) 0.076(3) 0.030(3) 0.014(3) -0.013(3) N5 0.054(3) 0.084(3) 0.062(2) 0.025(2) 0.013(2) -0.005(2) N6 0.051(2) 0.0395(19) 0.051(2) 0.0057(17) -0.0057(18) 0.0091(19) N7 0.039(2) 0.048(2) 0.047(2) 0.0071(19) 0.0001(18) -0.014(2) N8 0.054(2) 0.058(2) 0.081(3) 0.021(2) -0.017(2) 0.007(2) C1 0.039(3) 0.042(2) 0.042(3) 0.002(2) 0.005(2) 0.002(2) C2 0.043(3) 0.053(3) 0.039(2) 0.013(2) 0.008(2) 0.006(2) C3 0.044(3) 0.055(3) 0.043(3) 0.005(2) -0.002(2) -0.001(2) C4 0.040(2) 0.047(2) 0.038(2) 0.006(2) 0.0006(19) -0.007(2) C5 0.084(4) 0.106(4) 0.046(3) 0.015(3) -0.011(3) -0.020(3) C6 0.039(3) 0.036(2) 0.040(2) 0.0067(18) 0.008(2) 0.0037(19) C7 0.037(2) 0.040(2) 0.034(2) 0.0054(17) 0.0018(18) 0.007(2) C8 0.037(2) 0.036(2) 0.0338(19) 0.0057(18) 0.0065(18) 0.002(2) C9 0.037(2) 0.031(2) 0.040(2) 0.0059(18) 0.0090(19) 0.0035(19) C10 0.047(3) 0.035(2) 0.043(2) -0.0004(19) 0.013(2) 0.005(2) C11 0.069(3) 0.039(2) 0.051(2) -0.004(2) 0.010(2) 0.004(2) C12 0.078(4) 0.027(2) 0.047(2) -0.0025(19) 0.001(3) -0.008(2) C13 0.089(4) 0.040(2) 0.078(3) 0.009(3) -0.003(3) 0.005(3) C14 0.098(5) 0.051(3) 0.098(4) 0.011(3) -0.017(4) 0.000(3) C15 0.124(5) 0.047(3) 0.071(3) 0.022(2) -0.018(4) -0.010(4) C16 0.097(4) 0.066(3) 0.064(3) 0.014(3) 0.002(3) -0.026(3) C17 0.082(4) 0.053(3) 0.052(3) 0.003(2) -0.014(3) 0.000(3) C18 0.041(3) 0.054(2) 0.045(2) -0.002(2) 0.009(2) 0.004(2) C19 0.037(3) 0.041(2) 0.060(3) 0.000(2) 0.000(2) 0.004(2) C20 0.047(3) 0.037(2) 0.046(2) 0.0016(19) 0.003(2) -0.001(2) C21 0.054(3) 0.049(3) 0.052(3) -0.002(2) 0.001(2) 0.000(2) C22 0.073(4) 0.057(3) 0.060(3) -0.013(2) 0.010(3) 0.004(3) C23 0.101(4) 0.053(3) 0.050(3) -0.002(2) 0.002(3) -0.004(3) C24 0.093(4) 0.061(3) 0.058(3) 0.008(3) -0.016(3) -0.006(3) C25 0.068(3) 0.056(3) 0.058(3) 0.004(2) -0.006(3) 0.007(3) C26 0.045(3) 0.039(2) 0.040(2) 0.001(2) 0.002(2) 0.002(2) C27 0.044(3) 0.037(2) 0.031(2) 0.0020(18) 0.0040(19) 0.001(2) C28 0.058(3) 0.040(2) 0.055(3) -0.007(2) 0.002(2) -0.007(2) C29 0.093(4) 0.036(2) 0.059(3) -0.008(2) 0.014(3) 0.002(3) C30 0.074(4) 0.052(3) 0.049(3) 0.007(2) 0.015(2) 0.023(3) C31 0.049(3) 0.065(3) 0.054(3) 0.001(2) -0.003(2) 0.008(3) C32 0.050(3) 0.044(2) 0.044(2) -0.009(2) 0.003(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 C1 1.200(4) . ? O2 C6 1.415(4) . ? O2 C9 1.439(4) . ? O3 C8 1.410(4) . ? O3 C11 1.426(4) . ? O4 C19 1.341(5) . ? O4 C18 1.459(4) . ? O5 C19 1.208(4) . ? O6 C26 1.363(4) . ? O6 C10 1.447(4) . ? O7 C26 1.194(4) . ? N1 C1 1.378(5) . ? N1 C4 1.379(4) . ? N1 C6 1.471(4) . ? N2 C2 1.348(5) . ? N2 N3 1.369(4) . ? N2 C1 1.411(5) . ? N3 N4 1.295(5) . ? N4 N5 1.372(5) . ? N5 C2 1.334(5) . ? N6 N7 1.231(4) . ? N6 C7 1.485(4) . ? N7 N8 1.141(4) . ? C2 C3 1.405(5) . ? C3 C4 1.340(5) . ? C3 C5 1.503(5) . ? C4 H4 0.9500 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.553(5) . ? C6 H6 1.0000 . ? C7 C8 1.536(5) . ? C7 H7 1.0000 . ? C8 C9 1.531(5) . ? C8 H8 1.0000 . ? C9 C10 1.511(5) . ? C9 C18 1.514(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.502(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.357(6) . ? C12 C17 1.375(6) . ? C13 C14 1.365(6) . ? C13 H13 0.9500 . ? C14 C15 1.369(7) . ? C14 H14 0.9500 . ? C15 C16 1.378(7) . ? C15 H15 0.9500 . ? C16 C17 1.402(6) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.473(5) . ? C20 C25 1.386(5) . ? C20 C21 1.395(5) . ? C21 C22 1.376(5) . ? C21 H21 0.9500 . ? C22 C23 1.374(6) . ? C22 H22 0.9500 . ? C23 C24 1.380(6) . ? C23 H23 0.9500 . ? C24 C25 1.382(6) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.487(5) . ? C27 C32 1.385(5) . ? C27 C28 1.391(5) . ? C28 C29 1.370(6) . ? C28 H28 0.9500 . ? C29 C30 1.369(6) . ? C29 H29 0.9500 . ? C30 C31 1.381(6) . ? C30 H30 0.9500 . ? C31 C32 1.374(5) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? 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 C6 O2 C9 110.8(3) . . ? C8 O3 C11 115.7(3) . . ? C19 O4 C18 117.3(3) . . ? C26 O6 C10 116.1(3) . . ? C1 N1 C4 123.8(3) . . ? C1 N1 C6 115.1(3) . . ? C4 N1 C6 121.0(3) . . ? C2 N2 N3 109.9(3) . . ? C2 N2 C1 127.0(4) . . ? N3 N2 C1 123.1(4) . . ? N4 N3 N2 104.4(4) . . ? N3 N4 N5 112.7(4) . . ? C2 N5 N4 105.2(3) . . ? N7 N6 C7 115.9(3) . . ? N8 N7 N6 171.4(4) . . ? O1 C1 N1 125.7(3) . . ? O1 C1 N2 124.1(4) . . ? N1 C1 N2 110.3(4) . . ? N5 C2 N2 107.8(4) . . ? N5 C2 C3 132.6(4) . . ? N2 C2 C3 119.6(4) . . ? C4 C3 C2 115.3(4) . . ? C4 C3 C5 125.1(4) . . ? C2 C3 C5 119.6(4) . . ? C3 C4 N1 123.8(4) . . ? C3 C4 H4 118.1 . . ? N1 C4 H4 118.1 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O2 C6 N1 106.7(3) . . ? O2 C6 C7 107.1(3) . . ? N1 C6 C7 113.1(3) . . ? O2 C6 H6 109.9 . . ? N1 C6 H6 109.9 . . ? C7 C6 H6 109.9 . . ? N6 C7 C8 113.2(3) . . ? N6 C7 C6 105.6(3) . . ? C8 C7 C6 103.2(3) . . ? N6 C7 H7 111.5 . . ? C8 C7 H7 111.5 . . ? C6 C7 H7 111.5 . . ? O3 C8 C9 109.4(3) . . ? O3 C8 C7 114.9(3) . . ? C9 C8 C7 104.0(3) . . ? O3 C8 H8 109.4 . . ? C9 C8 H8 109.4 . . ? C7 C8 H8 109.4 . . ? O2 C9 C10 111.4(3) . . ? O2 C9 C18 106.1(3) . . ? C10 C9 C18 110.1(3) . . ? O2 C9 C8 103.3(3) . . ? C10 C9 C8 110.0(3) . . ? C18 C9 C8 115.7(3) . . ? O6 C10 C9 112.1(3) . . ? O6 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? O6 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? O3 C11 C12 107.3(3) . . ? O3 C11 H11A 110.3 . . ? C12 C11 H11A 110.3 . . ? O3 C11 H11B 110.3 . . ? C12 C11 H11B 110.3 . . ? H11A C11 H11B 108.5 . . ? C13 C12 C17 119.7(4) . . ? C13 C12 C11 119.6(5) . . ? C17 C12 C11 120.7(4) . . ? C12 C13 C14 121.1(5) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C15 119.8(5) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 120.9(4) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C17 118.1(5) . . ? C15 C16 H16 121.0 . . ? C17 C16 H16 121.0 . . ? C12 C17 C16 120.4(5) . . ? C12 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? O4 C18 C9 108.4(3) . . ? O4 C18 H18A 110.0 . . ? C9 C18 H18A 110.0 . . ? O4 C18 H18B 110.0 . . ? C9 C18 H18B 110.0 . . ? H18A C18 H18B 108.4 . . ? O5 C19 O4 122.1(4) . . ? O5 C19 C20 124.4(4) . . ? O4 C19 C20 113.5(4) . . ? C25 C20 C21 119.3(4) . . ? C25 C20 C19 118.7(4) . . ? C21 C20 C19 122.0(4) . . ? C22 C21 C20 120.2(4) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C23 C22 C21 120.5(5) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 119.4(4) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C23 C24 C25 121.0(5) . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? C24 C25 C20 119.6(4) . . ? C24 C25 H25 120.2 . . ? C20 C25 H25 120.2 . . ? O7 C26 O6 122.7(4) . . ? O7 C26 C27 125.8(4) . . ? O6 C26 C27 111.5(3) . . ? C32 C27 C28 119.1(4) . . ? C32 C27 C26 123.5(4) . . ? C28 C27 C26 117.3(4) . . ? C29 C28 C27 120.4(4) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C30 C29 C28 119.9(4) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C31 120.7(4) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C32 C31 C30 119.6(4) . . ? C32 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? C31 C32 C27 120.3(4) . . ? C31 C32 H32 119.8 . . ? C27 C32 H32 119.8 . . ? 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 C2 N2 N3 N4 0.3(4) . . . . ? C1 N2 N3 N4 179.6(4) . . . . ? N2 N3 N4 N5 -0.4(5) . . . . ? N3 N4 N5 C2 0.3(5) . . . . ? C7 N6 N7 N8 -172(2) . . . . ? C4 N1 C1 O1 173.4(4) . . . . ? C6 N1 C1 O1 -4.4(5) . . . . ? C4 N1 C1 N2 -6.7(5) . . . . ? C6 N1 C1 N2 175.5(3) . . . . ? C2 N2 C1 O1 -176.3(4) . . . . ? N3 N2 C1 O1 4.5(6) . . . . ? C2 N2 C1 N1 3.8(5) . . . . ? N3 N2 C1 N1 -175.4(3) . . . . ? N4 N5 C2 N2 0.0(5) . . . . ? N4 N5 C2 C3 179.5(4) . . . . ? N3 N2 C2 N5 -0.2(4) . . . . ? C1 N2 C2 N5 -179.5(3) . . . . ? N3 N2 C2 C3 -179.8(3) . . . . ? C1 N2 C2 C3 0.9(6) . . . . ? N5 C2 C3 C4 177.6(4) . . . . ? N2 C2 C3 C4 -3.0(5) . . . . ? N5 C2 C3 C5 -2.4(7) . . . . ? N2 C2 C3 C5 177.1(4) . . . . ? C2 C3 C4 N1 0.1(6) . . . . ? C5 C3 C4 N1 180.0(4) . . . . ? C1 N1 C4 C3 5.3(6) . . . . ? C6 N1 C4 C3 -177.0(4) . . . . ? C9 O2 C6 N1 -137.1(3) . . . . ? C9 O2 C6 C7 -15.8(4) . . . . ? C1 N1 C6 O2 -149.8(3) . . . . ? C4 N1 C6 O2 32.3(4) . . . . ? C1 N1 C6 C7 92.7(4) . . . . ? C4 N1 C6 C7 -85.2(4) . . . . ? N7 N6 C7 C8 -84.3(4) . . . . ? N7 N6 C7 C6 163.5(3) . . . . ? O2 C6 C7 N6 112.6(3) . . . . ? N1 C6 C7 N6 -130.1(3) . . . . ? O2 C6 C7 C8 -6.4(4) . . . . ? N1 C6 C7 C8 110.9(3) . . . . ? C11 O3 C8 C9 -155.1(3) . . . . ? C11 O3 C8 C7 88.4(4) . . . . ? N6 C7 C8 O3 30.2(4) . . . . ? C6 C7 C8 O3 143.7(3) . . . . ? N6 C7 C8 C9 -89.4(3) . . . . ? C6 C7 C8 C9 24.2(3) . . . . ? C6 O2 C9 C10 -86.9(4) . . . . ? C6 O2 C9 C18 153.4(3) . . . . ? C6 O2 C9 C8 31.2(4) . . . . ? O3 C8 C9 O2 -156.9(3) . . . . ? C7 C8 C9 O2 -33.6(3) . . . . ? O3 C8 C9 C10 -37.9(4) . . . . ? C7 C8 C9 C10 85.4(3) . . . . ? O3 C8 C9 C18 87.6(4) . . . . ? C7 C8 C9 C18 -149.1(3) . . . . ? C26 O6 C10 C9 102.7(4) . . . . ? O2 C9 C10 O6 -62.6(4) . . . . ? C18 C9 C10 O6 54.8(4) . . . . ? C8 C9 C10 O6 -176.6(3) . . . . ? C8 O3 C11 C12 -179.6(3) . . . . ? O3 C11 C12 C13 115.8(4) . . . . ? O3 C11 C12 C17 -62.5(5) . . . . ? C17 C12 C13 C14 -0.4(6) . . . . ? C11 C12 C13 C14 -178.7(4) . . . . ? C12 C13 C14 C15 0.3(7) . . . . ? C13 C14 C15 C16 -0.5(8) . . . . ? C14 C15 C16 C17 0.7(7) . . . . ? C13 C12 C17 C16 0.6(6) . . . . ? C11 C12 C17 C16 178.9(3) . . . . ? C15 C16 C17 C12 -0.8(6) . . . . ? C19 O4 C18 C9 151.1(3) . . . . ? O2 C9 C18 O4 -69.8(3) . . . . ? C10 C9 C18 O4 169.6(3) . . . . ? C8 C9 C18 O4 44.1(4) . . . . ? C18 O4 C19 O5 -6.9(5) . . . . ? C18 O4 C19 C20 172.2(3) . . . . ? O5 C19 C20 C25 3.1(6) . . . . ? O4 C19 C20 C25 -176.1(3) . . . . ? O5 C19 C20 C21 -179.7(4) . . . . ? O4 C19 C20 C21 1.2(5) . . . . ? C25 C20 C21 C22 -0.3(6) . . . . ? C19 C20 C21 C22 -177.6(4) . . . . ? C20 C21 C22 C23 0.4(6) . . . . ? C21 C22 C23 C24 -0.6(7) . . . . ? C22 C23 C24 C25 0.8(7) . . . . ? C23 C24 C25 C20 -0.7(7) . . . . ? C21 C20 C25 C24 0.4(6) . . . . ? C19 C20 C25 C24 177.8(4) . . . . ? C10 O6 C26 O7 -9.2(5) . . . . ? C10 O6 C26 C27 169.0(3) . . . . ? O7 C26 C27 C32 -178.4(4) . . . . ? O6 C26 C27 C32 3.5(5) . . . . ? O7 C26 C27 C28 3.5(6) . . . . ? O6 C26 C27 C28 -174.6(3) . . . . ? C32 C27 C28 C29 -0.7(6) . . . . ? C26 C27 C28 C29 177.4(3) . . . . ? C27 C28 C29 C30 0.5(6) . . . . ? C28 C29 C30 C31 0.5(6) . . . . ? C29 C30 C31 C32 -1.2(6) . . . . ? C30 C31 C32 C27 1.0(6) . . . . ? C28 C27 C32 C31 0.0(6) . . . . ? C26 C27 C32 C31 -178.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 21.51 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.212 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.045