Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'David Procter' _publ_contact_author_address ; Department of Chemistry The University of Manchester Oxford Road Manchester M13 9PL UNITED KINGDOM ; _publ_contact_author_email DAVID.J.PROCTER@MANCHESTER.AC.UK _publ_section_title ; Synthesis and evaluation of a new polymer-supported pseudoephedrine auxiliary for asymmetric alkylations on solid phase ; _publ_section_exptl_refinement ; The structure was solved by direct methods. All non-H atoms were refined anisotropically. H atoms were included in calculated positions. ; loop_ _publ_author_name 'David Procter' 'Jean-Claude Kizirian' 'Andrea M. McGhee' data_s2198abs _database_code_depnum_ccdc_archive 'CCDC 632894' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H29 N O2' _chemical_formula_weight 387.50 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.4065(12) _cell_length_b 9.6892(14) _cell_length_c 26.482(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2157.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5907 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 26.37 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9567 _exptl_absorpt_correction_T_max 0.9780 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 11625 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.46 _reflns_number_total 2557 _reflns_number_gt 2402 _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. Refinement of the Flack parameter gave a senseless value due to the lack of anomalous scatterer in the molecule, thus the Friedel pairs were merged for the final refinement; the absolute configuration was assigned by reference to an unchanging chiral centre in the synthetic procedure. ; _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^)+(0.0674P)^2^+0.2932P] 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 ? _chemical_absolute_configuration syn _refine_ls_number_reflns 2557 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.177 _refine_ls_restrained_S_all 1.177 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3902(2) 0.11284(18) 0.94214(7) 0.0179(4) Uani 1 1 d . . . O1 O 0.3914(2) 0.12291(16) 1.04665(6) 0.0214(3) Uani 1 1 d . . . H1 H 0.3094 0.1724 1.0475 0.032 Uiso 1 1 calc R . . O2 O 0.6326(2) 0.21014(16) 0.95253(6) 0.0231(4) Uani 1 1 d . . . C1 C 0.3280(3) -0.2523(2) 1.05404(9) 0.0235(5) Uani 1 1 d . . . H1A H 0.2528 -0.2678 1.0279 0.028 Uiso 1 1 calc R . . C2 C 0.3639(3) -0.3582(2) 1.08777(9) 0.0260(5) Uani 1 1 d . . . H2 H 0.3144 -0.4459 1.0843 0.031 Uiso 1 1 calc R . . C3 C 0.4724(3) -0.3352(2) 1.12637(9) 0.0270(5) Uani 1 1 d . . . H3 H 0.4949 -0.4063 1.1500 0.032 Uiso 1 1 calc R . . C4 C 0.5478(3) -0.2087(3) 1.13043(9) 0.0270(5) Uani 1 1 d . . . H4 H 0.6242 -0.1941 1.1563 0.032 Uiso 1 1 calc R . . C5 C 0.5123(3) -0.1026(2) 1.09672(8) 0.0219(5) Uani 1 1 d . . . H5 H 0.5638 -0.0157 1.0999 0.026 Uiso 1 1 calc R . . C6 C 0.4012(3) -0.1235(2) 1.05829(8) 0.0187(4) Uani 1 1 d . . . C7 C 0.3548(3) -0.0055(2) 1.02340(8) 0.0182(4) Uani 1 1 d . . . H7 H 0.2373 -0.0097 1.0176 0.022 Uiso 1 1 calc R . . C8 C 0.4390(3) -0.0095(2) 0.97156(8) 0.0178(4) Uani 1 1 d . . . H8 H 0.5559 -0.0016 0.9779 0.021 Uiso 1 1 calc R . . C9 C 0.4937(3) 0.2185(2) 0.93705(8) 0.0184(4) Uani 1 1 d . . . C10 C 0.4360(3) 0.3492(2) 0.91089(8) 0.0192(4) Uani 1 1 d . . . H10 H 0.3362 0.3268 0.8920 0.023 Uiso 1 1 calc R . . C11 C 0.5624(3) 0.3959(2) 0.87247(8) 0.0217(5) Uani 1 1 d . . . H11A H 0.6549 0.4340 0.8909 0.026 Uiso 1 1 calc R . . H11B H 0.5994 0.3146 0.8531 0.026 Uiso 1 1 calc R . . C12 C 0.5006(3) 0.5035(2) 0.83615(8) 0.0202(5) Uani 1 1 d . . . C13 C 0.5603(3) 0.6376(2) 0.83607(8) 0.0226(5) Uani 1 1 d . . . H13 H 0.6405 0.6628 0.8596 0.027 Uiso 1 1 calc R . . C14 C 0.5039(3) 0.7349(2) 0.80198(9) 0.0252(5) Uani 1 1 d . . . H14 H 0.5454 0.8261 0.8025 0.030 Uiso 1 1 calc R . . C15 C 0.3882(3) 0.6999(2) 0.76746(9) 0.0256(5) Uani 1 1 d . . . H15 H 0.3505 0.7666 0.7441 0.031 Uiso 1 1 calc R . . C16 C 0.3267(3) 0.5666(3) 0.76695(9) 0.0246(5) Uani 1 1 d . . . H16 H 0.2465 0.5423 0.7433 0.030 Uiso 1 1 calc R . . C17 C 0.3825(3) 0.4692(2) 0.80102(8) 0.0224(5) Uani 1 1 d . . . H17 H 0.3401 0.3783 0.8005 0.027 Uiso 1 1 calc R . . C18 C 0.4115(3) -0.1424(2) 0.94164(8) 0.0216(5) Uani 1 1 d . . . H18A H 0.2973 -0.1550 0.9359 0.032 Uiso 1 1 calc R . . H18B H 0.4530 -0.2211 0.9608 0.032 Uiso 1 1 calc R . . H18C H 0.4666 -0.1363 0.9091 0.032 Uiso 1 1 calc R . . C19 C 0.2204(3) 0.1256(2) 0.92770(8) 0.0177(4) Uani 1 1 d . . . H19A H 0.1764 0.2096 0.9438 0.021 Uiso 1 1 calc R . . H19B H 0.1620 0.0453 0.9415 0.021 Uiso 1 1 calc R . . C20 C 0.1893(3) 0.1335(2) 0.87136(8) 0.0179(4) Uani 1 1 d . . . C21 C 0.0552(3) 0.2050(2) 0.85463(9) 0.0226(5) Uani 1 1 d . . . H21 H -0.0122 0.2496 0.8784 0.027 Uiso 1 1 calc R . . C22 C 0.0199(3) 0.2113(3) 0.80371(9) 0.0277(5) Uani 1 1 d . . . H22 H -0.0710 0.2611 0.7926 0.033 Uiso 1 1 calc R . . C23 C 0.1160(3) 0.1453(3) 0.76859(9) 0.0278(5) Uani 1 1 d . . . H23 H 0.0906 0.1490 0.7337 0.033 Uiso 1 1 calc R . . C24 C 0.2489(3) 0.0743(2) 0.78483(9) 0.0242(5) Uani 1 1 d . . . H24 H 0.3154 0.0292 0.7610 0.029 Uiso 1 1 calc R . . C25 C 0.2858(3) 0.0686(2) 0.83597(8) 0.0208(5) Uani 1 1 d . . . H25 H 0.3778 0.0200 0.8468 0.025 Uiso 1 1 calc R . . C26 C 0.3966(3) 0.4591(2) 0.95075(9) 0.0222(5) Uani 1 1 d . . . H26A H 0.3125 0.4246 0.9731 0.033 Uiso 1 1 calc R . . H26B H 0.3602 0.5435 0.9339 0.033 Uiso 1 1 calc R . . H26C H 0.4919 0.4794 0.9707 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0189(9) 0.0130(8) 0.0216(9) 0.0010(7) -0.0018(7) -0.0007(8) O1 0.0228(8) 0.0143(7) 0.0271(8) -0.0039(6) -0.0023(7) 0.0038(7) O2 0.0205(8) 0.0167(7) 0.0321(8) 0.0043(6) -0.0057(7) -0.0035(7) C1 0.0230(12) 0.0215(11) 0.0260(11) 0.0002(9) 0.0017(9) 0.0004(10) C2 0.0296(12) 0.0144(10) 0.0340(12) 0.0024(9) 0.0056(10) 0.0029(10) C3 0.0324(14) 0.0215(11) 0.0272(12) 0.0082(9) 0.0063(10) 0.0118(11) C4 0.0262(12) 0.0307(12) 0.0241(11) 0.0022(10) -0.0017(10) 0.0091(11) C5 0.0210(11) 0.0190(10) 0.0257(11) -0.0008(8) 0.0018(9) 0.0027(10) C6 0.0174(10) 0.0170(10) 0.0216(10) -0.0002(8) 0.0047(8) 0.0038(9) C7 0.0172(10) 0.0142(10) 0.0231(10) -0.0009(8) -0.0010(8) -0.0005(9) C8 0.0187(10) 0.0114(9) 0.0232(10) 0.0018(8) -0.0008(8) -0.0002(9) C9 0.0213(11) 0.0140(9) 0.0201(10) -0.0016(8) 0.0000(8) 0.0006(9) C10 0.0214(11) 0.0150(10) 0.0211(10) 0.0005(8) -0.0030(9) -0.0022(9) C11 0.0244(11) 0.0177(10) 0.0229(10) 0.0016(8) -0.0002(9) 0.0002(10) C12 0.0227(11) 0.0175(10) 0.0205(10) -0.0006(8) 0.0025(9) 0.0017(10) C13 0.0273(12) 0.0186(10) 0.0217(10) -0.0022(9) 0.0022(9) -0.0032(10) C14 0.0332(13) 0.0163(10) 0.0260(11) 0.0001(8) 0.0069(10) -0.0009(10) C15 0.0310(13) 0.0217(11) 0.0242(11) 0.0059(9) 0.0038(10) 0.0074(11) C16 0.0234(12) 0.0251(12) 0.0254(11) -0.0005(9) -0.0025(10) 0.0030(10) C17 0.0242(12) 0.0178(10) 0.0252(11) -0.0010(8) 0.0015(9) -0.0009(10) C18 0.0266(12) 0.0129(9) 0.0253(11) 0.0002(8) -0.0014(9) 0.0008(9) C19 0.0166(10) 0.0139(10) 0.0227(10) 0.0009(8) 0.0002(8) -0.0015(9) C20 0.0180(10) 0.0115(9) 0.0242(10) -0.0001(8) -0.0008(8) -0.0047(9) C21 0.0217(11) 0.0181(10) 0.0281(11) -0.0006(9) -0.0014(9) -0.0005(10) C22 0.0248(12) 0.0271(12) 0.0311(12) 0.0015(10) -0.0073(10) -0.0008(11) C23 0.0343(13) 0.0271(12) 0.0220(10) 0.0005(9) -0.0063(10) -0.0080(12) C24 0.0316(13) 0.0182(11) 0.0227(11) -0.0021(9) 0.0043(10) -0.0041(10) C25 0.0216(11) 0.0154(10) 0.0255(11) 0.0002(8) 0.0004(10) 0.0011(9) C26 0.0218(12) 0.0169(10) 0.0278(11) -0.0018(9) -0.0006(10) 0.0001(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C9 1.350(3) . ? N1 C8 1.477(3) . ? N1 C19 1.483(3) . ? O1 C7 1.422(3) . ? O1 H1 0.8400 . ? O2 C9 1.241(3) . ? C1 C2 1.394(3) . ? C1 C6 1.396(3) . ? C1 H1A 0.9500 . ? C2 C3 1.388(4) . ? C2 H2 0.9500 . ? C3 C4 1.385(4) . ? C3 H3 0.9500 . ? C4 C5 1.394(3) . ? C4 H4 0.9500 . ? C5 C6 1.396(3) . ? C5 H5 0.9500 . ? C6 C7 1.521(3) . ? C7 C8 1.545(3) . ? C7 H7 1.0000 . ? C8 C18 1.530(3) . ? C8 H8 1.0000 . ? C9 C10 1.523(3) . ? C10 C26 1.536(3) . ? C10 C11 1.539(3) . ? C10 H10 1.0000 . ? C11 C12 1.511(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.393(3) . ? C12 C17 1.400(3) . ? C13 C14 1.389(3) . ? C13 H13 0.9500 . ? C14 C15 1.377(4) . ? C14 H14 0.9500 . ? C15 C16 1.392(4) . ? C15 H15 0.9500 . ? C16 C17 1.387(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.517(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C25 1.390(3) . ? C20 C21 1.395(3) . ? C21 C22 1.382(3) . ? C21 H21 0.9500 . ? C22 C23 1.388(4) . ? C22 H22 0.9500 . ? C23 C24 1.381(4) . ? C23 H23 0.9500 . ? C24 C25 1.390(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 C9 N1 C8 118.85(19) . . ? C9 N1 C19 122.09(18) . . ? C8 N1 C19 118.05(18) . . ? C7 O1 H1 109.5 . . ? C2 C1 C6 120.7(2) . . ? C2 C1 H1A 119.6 . . ? C6 C1 H1A 119.6 . . ? C3 C2 C1 119.7(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.2(2) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 118.9(2) . . ? C5 C6 C7 120.3(2) . . ? C1 C6 C7 120.6(2) . . ? O1 C7 C6 109.83(17) . . ? O1 C7 C8 107.93(17) . . ? C6 C7 C8 113.77(18) . . ? O1 C7 H7 108.4 . . ? C6 C7 H7 108.4 . . ? C8 C7 H7 108.4 . . ? N1 C8 C18 111.15(17) . . ? N1 C8 C7 108.74(17) . . ? C18 C8 C7 114.35(18) . . ? N1 C8 H8 107.4 . . ? C18 C8 H8 107.4 . . ? C7 C8 H8 107.4 . . ? O2 C9 N1 121.6(2) . . ? O2 C9 C10 120.3(2) . . ? N1 C9 C10 118.10(19) . . ? C9 C10 C26 109.43(17) . . ? C9 C10 C11 108.97(19) . . ? C26 C10 C11 113.57(18) . . ? C9 C10 H10 108.2 . . ? C26 C10 H10 108.2 . . ? C11 C10 H10 108.2 . . ? C12 C11 C10 112.70(19) . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C17 118.4(2) . . ? C13 C12 C11 121.4(2) . . ? C17 C12 C11 120.2(2) . . ? C14 C13 C12 120.8(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 120.3(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.8(2) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 120.0(2) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 120.7(2) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 C20 115.11(18) . . ? N1 C19 H19A 108.5 . . ? C20 C19 H19A 108.5 . . ? N1 C19 H19B 108.5 . . ? C20 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? C25 C20 C21 118.8(2) . . ? C25 C20 C19 122.7(2) . . ? C21 C20 C19 118.5(2) . . ? C22 C21 C20 120.3(2) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 120.6(2) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 119.5(2) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C23 C24 C25 120.2(2) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C24 C25 C20 120.6(2) . . ? C24 C25 H25 119.7 . . ? C20 C25 H25 119.7 . . ? C10 C26 H26A 109.5 . . ? C10 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C10 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? 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 0.7(4) . . . . ? C1 C2 C3 C4 -1.8(4) . . . . ? C2 C3 C4 C5 1.8(4) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C4 C5 C6 C7 176.3(2) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C2 C1 C6 C7 -176.4(2) . . . . ? C5 C6 C7 O1 -20.8(3) . . . . ? C1 C6 C7 O1 156.0(2) . . . . ? C5 C6 C7 C8 100.3(2) . . . . ? C1 C6 C7 C8 -82.9(3) . . . . ? C9 N1 C8 C18 -128.6(2) . . . . ? C19 N1 C8 C18 62.6(2) . . . . ? C9 N1 C8 C7 104.6(2) . . . . ? C19 N1 C8 C7 -64.1(2) . . . . ? O1 C7 C8 N1 -55.3(2) . . . . ? C6 C7 C8 N1 -177.46(18) . . . . ? O1 C7 C8 C18 179.81(18) . . . . ? C6 C7 C8 C18 57.7(3) . . . . ? C8 N1 C9 O2 6.5(3) . . . . ? C19 N1 C9 O2 174.8(2) . . . . ? C8 N1 C9 C10 -174.32(17) . . . . ? C19 N1 C9 C10 -6.0(3) . . . . ? O2 C9 C10 C26 -79.6(3) . . . . ? N1 C9 C10 C26 101.2(2) . . . . ? O2 C9 C10 C11 45.1(3) . . . . ? N1 C9 C10 C11 -134.1(2) . . . . ? C9 C10 C11 C12 166.32(18) . . . . ? C26 C10 C11 C12 -71.4(2) . . . . ? C10 C11 C12 C13 114.2(2) . . . . ? C10 C11 C12 C17 -66.8(3) . . . . ? C17 C12 C13 C14 0.0(3) . . . . ? C11 C12 C13 C14 179.1(2) . . . . ? C12 C13 C14 C15 -0.3(4) . . . . ? C13 C14 C15 C16 0.4(4) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? C15 C16 C17 C12 0.0(4) . . . . ? C13 C12 C17 C16 0.1(3) . . . . ? C11 C12 C17 C16 -178.9(2) . . . . ? C9 N1 C19 C20 70.9(3) . . . . ? C8 N1 C19 C20 -120.70(19) . . . . ? N1 C19 C20 C25 30.8(3) . . . . ? N1 C19 C20 C21 -151.4(2) . . . . ? C25 C20 C21 C22 -0.2(3) . . . . ? C19 C20 C21 C22 -178.1(2) . . . . ? C20 C21 C22 C23 0.7(4) . . . . ? C21 C22 C23 C24 -0.7(4) . . . . ? C22 C23 C24 C25 0.2(4) . . . . ? C23 C24 C25 C20 0.3(3) . . . . ? C21 C20 C25 C24 -0.3(3) . . . . ? C19 C20 C25 C24 177.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.84 1.87 2.711(2) 177.0 4_457 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.405 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.057