Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name _publ_author_address 'Philip Kocienski' ;Department of Chemistry University of Leeds Leeds, LS2 9JT, UK ; 'Gilbert Besong' ;Department of Chemistry University of Leeds Leeds, LS2 9JT, UK ; 'F. Thomas Boyle' '' 'Krzysztof Jarowicki' '' 'Eric Sliwinski' '' _publ_contact_author_name 'Philip Kocienski' _publ_contact_author_address ; Chemistry Leeds University Leeds LS2 9JT UNITED KINGDOM ; _publ_contact_author_email P.J.KOCIENSKI@LEEDS.AC.UK _publ_section_title ; Synthesis of (S)-(-)-N-Acetylcolchinol Using Intramolecular Biaryl Oxidative Coupling ; _publ_contact_author_phone '+44 (0)113 34 36555' data_es443 _database_code_depnum_ccdc_archive 'CCDC 601950' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H31 N O5 S, C H2 Cl2' _chemical_formula_sum 'C23 H33 Cl2 N O5 S' _chemical_formula_weight 506.46 _chemical_absolute_configuration rmad 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.7734(11) _cell_length_b 13.3223(16) _cell_length_c 20.380(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2653.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5763 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 23.09 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.355 _exptl_absorpt_correction_type none _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator ; graphite model mounted in "parallel" mode ; _diffrn_measurement_device_type ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_radiation_detector 'Apex camera' _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 100306 _diffrn_reflns_av_R_equivalents 0.0831 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5205 _reflns_number_gt 4212 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker-Nonius, 2004)' _computing_cell_refinement 'Apex2 (Bruker-Nonius, 2004)' _computing_data_reduction ; SAINT enbedded in Apex2 (Bruker-Nonius, 2004) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material 'local program' _refine_special_details ; The structure solved in spacegroup P21 21 21 and the asymmetric unit contains one molecule of the title compound and one molecule of dichloromethane. Hydrogen atoms, H(31) and H(8), attached to N(31) and O(8) respectively, were found from the Fourier difference map and H(31) was found to be positioned pyramidally. Both the position and thermal parameters of H(31) and H(8) were allowed to freely refine resulting in a N-H distance of: N(31)-H(31), 0.82A and an O-H distance of O(8)-H(8), 0.79A. All other hydrogen atoms were positioned geometrically with the following carbon-hydrogen distances: aromatic, 0.95A; methyl, 0.98A; methylene, 0.99A; methine, 1.00A. All carbon Uiso(H) values were constrained to be 1.2 times Ueq of the parent atom. The absolute configuration was established since the molecule contained a chiral reference of known absolute configuration and this was confirmed by anomalous dispersion effects since the Flack parameter refined to 0.04(10). C.Kilner 28 March 2006 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^)+(0.0978P)^2^+1.4260P] 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 2257 Friedel pairs ; _refine_ls_abs_structure_Flack 0.04(10) _refine_ls_number_reflns 5205 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1601 _refine_ls_wR_factor_gt 0.1448 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.7667(4) -0.2208(3) 0.1293(2) 0.0287(8) Uani 1 1 d . . . H1A H 0.7022 -0.2032 0.1649 0.034 Uiso 1 1 calc R . . H1B H 0.7120 -0.2399 0.0903 0.034 Uiso 1 1 calc R . . C1S C 1.3828(10) -0.1926(6) 0.0418(4) 0.116(3) Uani 1 1 d . . . H1SA H 1.4555 -0.1575 0.0667 0.140 Uiso 1 1 calc R . . H1SB H 1.4057 -0.1902 -0.0055 0.140 Uiso 1 1 calc R . . C2 C 0.8536(4) -0.1288(3) 0.11249(17) 0.0243(8) Uani 1 1 d . . . H2A H 0.9167 -0.1462 0.0762 0.029 Uiso 1 1 calc R . . H2B H 0.9099 -0.1109 0.1511 0.029 Uiso 1 1 calc R . . C3 C 0.7680(3) -0.0368(3) 0.09215(16) 0.0210(7) Uani 1 1 d . . . H3 H 0.7036 -0.0588 0.0568 0.025 Uiso 1 1 calc R . . C4 C 0.8570(3) 0.0468(3) 0.06408(16) 0.0206(7) Uani 1 1 d . . . C5 C 0.9766(4) 0.0770(3) 0.09600(17) 0.0283(8) Uani 1 1 d . . . H5 H 1.0039 0.0448 0.1355 0.034 Uiso 1 1 calc R . . C6 C 1.0556(4) 0.1542(3) 0.06996(18) 0.0311(8) Uani 1 1 d . . . H6 H 1.1355 0.1754 0.0926 0.037 Uiso 1 1 calc R . . C7 C 1.0198(4) 0.2007(3) 0.01160(17) 0.0251(7) Uani 1 1 d . . . H7 H 1.0753 0.2524 -0.0063 0.030 Uiso 1 1 calc R . . C8 C 0.9010(4) 0.1699(3) -0.02021(18) 0.0254(8) Uani 1 1 d . . . C9 C 0.8205(3) 0.0933(3) 0.00570(16) 0.0223(7) Uani 1 1 d . . . H9 H 0.7401 0.0727 -0.0167 0.027 Uiso 1 1 calc R . . C11 C 0.8520(4) -0.3094(3) 0.15048(17) 0.0252(8) Uani 1 1 d . . . C12 C 0.9560(4) -0.2972(2) 0.19682(17) 0.0247(7) Uani 1 1 d . . . H12 H 0.9732 -0.2327 0.2149 0.030 Uiso 1 1 calc R . . C13 C 1.0341(4) -0.3785(2) 0.21658(16) 0.0230(7) Uani 1 1 d . . . C14 C 1.0056(3) -0.4748(2) 0.19334(16) 0.0234(8) Uani 1 1 d . . . C15 C 0.9007(4) -0.4874(3) 0.14734(17) 0.0268(8) Uani 1 1 d . . . C16 C 0.8259(4) -0.4046(3) 0.12559(18) 0.0273(8) Uani 1 1 d . . . H16 H 0.7565 -0.4134 0.0935 0.033 Uiso 1 1 calc R . . C17 C 1.1662(4) -0.2738(3) 0.2873(2) 0.0393(10) Uani 1 1 d . . . H17A H 1.2443 -0.2772 0.3174 0.047 Uiso 1 1 calc R . . H17B H 1.0849 -0.2513 0.3113 0.047 Uiso 1 1 calc R . . H17C H 1.1864 -0.2262 0.2519 0.047 Uiso 1 1 calc R . . C18 C 1.1728(4) -0.5999(3) 0.1738(2) 0.0333(9) Uani 1 1 d . . . H18A H 1.2193 -0.6565 0.1948 0.040 Uiso 1 1 calc R . . H18B H 1.2406 -0.5494 0.1607 0.040 Uiso 1 1 calc R . . H18C H 1.1237 -0.6237 0.1348 0.040 Uiso 1 1 calc R . . C19 C 0.7766(5) -0.6013(3) 0.0790(2) 0.0505(12) Uani 1 1 d . . . H19A H 0.7718 -0.6732 0.0691 0.061 Uiso 1 1 calc R . . H19B H 0.7993 -0.5641 0.0390 0.061 Uiso 1 1 calc R . . H19C H 0.6879 -0.5784 0.0958 0.061 Uiso 1 1 calc R . . C31 C 0.4479(3) 0.0326(3) 0.21200(17) 0.0284(8) Uani 1 1 d . . . C32 C 0.3031(4) 0.0723(4) 0.1993(2) 0.0434(11) Uani 1 1 d . . . H32A H 0.2492 0.0681 0.2398 0.052 Uiso 1 1 calc R . . H32B H 0.2593 0.0318 0.1651 0.052 Uiso 1 1 calc R . . H32C H 0.3081 0.1424 0.1849 0.052 Uiso 1 1 calc R . . C33 C 0.5177(4) 0.0951(3) 0.26512(18) 0.0363(9) Uani 1 1 d . . . H33A H 0.4689 0.0865 0.3068 0.044 Uiso 1 1 calc R . . H33B H 0.5163 0.1660 0.2525 0.044 Uiso 1 1 calc R . . H33C H 0.6126 0.0728 0.2703 0.044 Uiso 1 1 calc R . . C34 C 0.4441(4) -0.0792(3) 0.2296(2) 0.0391(10) Uani 1 1 d . . . H34A H 0.3983 -0.0880 0.2720 0.047 Uiso 1 1 calc R . . H34B H 0.5378 -0.1051 0.2324 0.047 Uiso 1 1 calc R . . H34C H 0.3939 -0.1160 0.1957 0.047 Uiso 1 1 calc R . . N31 N 0.6847(3) -0.0049(2) 0.14909(15) 0.0208(6) Uani 1 1 d . . . H31 H 0.725(4) 0.024(3) 0.1767(18) 0.019(10) Uiso 1 1 d . . . O8 O 0.8604(3) 0.2118(2) -0.07857(14) 0.0388(7) Uani 1 1 d . . . H8 H 0.911(4) 0.261(3) -0.095(2) 0.034(11) Uiso 1 1 d . . . O13 O 1.1415(2) -0.37130(17) 0.25991(13) 0.0277(6) Uani 1 1 d . . . O14 O 1.0769(3) -0.55576(19) 0.21918(12) 0.0292(6) Uani 1 1 d . . . O15 O 0.8793(3) -0.58407(19) 0.12730(14) 0.0389(7) Uani 1 1 d . . . O31 O 0.5475(3) 0.15807(19) 0.12350(13) 0.0339(6) Uani 1 1 d . . . Cl1S Cl 1.2249(2) -0.1371(2) 0.05609(10) 0.1101(7) Uani 1 1 d . . . Cl2S Cl 1.3658(5) -0.3298(2) 0.07110(12) 0.1702(14) Uani 1 1 d . . . S31 S 0.53520(8) 0.04660(6) 0.13252(4) 0.0237(2) Uani 1 1 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 C1 0.0256(17) 0.0212(19) 0.039(2) 0.0071(16) -0.0077(17) 0.0009(14) C1S 0.138(8) 0.114(7) 0.097(5) -0.024(5) -0.051(6) -0.018(6) C2 0.0228(17) 0.0213(19) 0.0287(18) 0.0035(14) 0.0035(14) 0.0044(14) C3 0.0208(15) 0.0197(17) 0.0224(15) 0.0025(13) -0.0019(13) 0.0000(14) C4 0.0184(15) 0.0185(17) 0.0249(16) 0.0030(14) 0.0026(13) 0.0034(14) C5 0.0243(17) 0.033(2) 0.0279(17) 0.0100(14) -0.0036(15) -0.0020(16) C6 0.0222(18) 0.038(2) 0.0328(19) -0.0020(16) -0.0046(16) -0.0050(16) C7 0.0227(17) 0.0216(17) 0.0309(18) 0.0014(14) 0.0029(15) -0.0019(15) C8 0.0233(17) 0.0236(19) 0.0292(18) 0.0045(15) 0.0000(15) 0.0008(15) C9 0.0169(16) 0.0245(18) 0.0255(17) 0.0013(14) -0.0031(13) -0.0019(13) C11 0.0214(17) 0.0206(17) 0.0335(19) 0.0058(14) 0.0022(15) 0.0003(14) C12 0.0238(17) 0.0169(16) 0.0334(18) 0.0004(13) 0.0027(16) 0.0018(15) C13 0.0200(16) 0.0247(18) 0.0244(16) 0.0033(13) 0.0032(15) 0.0010(15) C14 0.0250(18) 0.0180(17) 0.0273(17) 0.0025(13) 0.0025(13) 0.0060(13) C15 0.0348(19) 0.0188(18) 0.0267(18) -0.0017(14) 0.0011(15) 0.0026(15) C16 0.0274(18) 0.0232(19) 0.0311(18) 0.0003(15) -0.0060(16) 0.0021(14) C17 0.039(2) 0.021(2) 0.058(3) -0.0028(18) -0.021(2) 0.0009(17) C18 0.032(2) 0.027(2) 0.040(2) -0.0055(17) -0.0031(17) 0.0052(16) C19 0.064(3) 0.030(2) 0.057(3) -0.012(2) -0.027(3) 0.004(2) C31 0.0192(17) 0.038(2) 0.0277(17) 0.0030(15) 0.0022(14) 0.0012(16) C32 0.0189(18) 0.073(3) 0.039(2) 0.001(2) 0.0035(16) 0.0097(19) C33 0.0273(19) 0.050(2) 0.0315(19) -0.0052(18) 0.0028(17) -0.0040(18) C34 0.036(2) 0.040(2) 0.041(2) 0.0078(17) 0.0098(19) -0.0112(18) N31 0.0185(14) 0.0179(15) 0.0262(15) 0.0006(12) -0.0024(12) 0.0013(11) O8 0.0340(15) 0.0416(17) 0.0409(15) 0.0256(13) -0.0115(13) -0.0176(14) O13 0.0242(12) 0.0201(13) 0.0387(14) -0.0005(10) -0.0084(11) 0.0021(10) O14 0.0357(13) 0.0213(13) 0.0306(13) 0.0003(10) -0.0033(11) 0.0103(11) O15 0.0526(17) 0.0181(13) 0.0461(16) -0.0066(12) -0.0218(15) 0.0024(12) O31 0.0281(13) 0.0273(14) 0.0462(15) 0.0149(12) 0.0024(13) 0.0080(11) Cl1S 0.0813(13) 0.160(2) 0.0892(13) -0.0206(13) 0.0085(10) -0.0036(13) Cl2S 0.277(4) 0.145(2) 0.0883(15) 0.0267(15) -0.045(2) 0.017(3) S31 0.0171(4) 0.0274(5) 0.0264(4) 0.0060(4) -0.0006(3) 0.0039(4) _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 C11 1.508(5) . ? C1 C2 1.531(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1S Cl1S 1.736(10) . ? C1S Cl2S 1.930(9) . ? C1S H1SA 0.9900 . ? C1S H1SB 0.9900 . ? C2 C3 1.541(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N31 1.480(4) . ? C3 C4 1.525(5) . ? C3 H3 1.0000 . ? C4 C9 1.388(5) . ? C4 C5 1.397(5) . ? C5 C6 1.392(5) . ? C5 H5 0.9500 . ? C6 C7 1.386(5) . ? C6 H6 0.9500 . ? C7 C8 1.392(5) . ? C7 H7 0.9500 . ? C8 O8 1.373(4) . ? C8 C9 1.392(5) . ? C9 H9 0.9500 . ? C11 C16 1.389(5) . ? C11 C12 1.397(5) . ? C12 C13 1.386(5) . ? C12 H12 0.9500 . ? C13 O13 1.375(4) . ? C13 C14 1.396(5) . ? C14 O14 1.387(4) . ? C14 C15 1.399(5) . ? C15 O15 1.367(4) . ? C15 C16 1.396(5) . ? C16 H16 0.9500 . ? C17 O13 1.435(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O14 1.443(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 O15 1.425(5) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C31 C33 1.527(5) . ? C31 C34 1.532(5) . ? C31 C32 1.533(5) . ? C31 S31 1.840(3) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? N31 S31 1.649(3) . ? N31 H31 0.79(4) . ? O8 H8 0.89(4) . ? O31 S31 1.501(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 C11 C1 C2 112.6(3) . . ? C11 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? C11 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? Cl1S C1S Cl2S 106.0(5) . . ? Cl1S C1S H1SA 110.5 . . ? Cl2S C1S H1SA 110.5 . . ? Cl1S C1S H1SB 110.5 . . ? Cl2S C1S H1SB 110.5 . . ? H1SA C1S H1SB 108.7 . . ? C1 C2 C3 113.3(3) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? N31 C3 C4 113.4(3) . . ? N31 C3 C2 108.5(3) . . ? C4 C3 C2 111.8(3) . . ? N31 C3 H3 107.6 . . ? C4 C3 H3 107.6 . . ? C2 C3 H3 107.6 . . ? C9 C4 C5 119.1(3) . . ? C9 C4 C3 120.1(3) . . ? C5 C4 C3 120.9(3) . . ? C6 C5 C4 120.0(3) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 121.2(3) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 118.6(3) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? O8 C8 C9 117.6(3) . . ? O8 C8 C7 121.6(3) . . ? C9 C8 C7 120.7(3) . . ? C4 C9 C8 120.5(3) . . ? C4 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C16 C11 C12 119.1(3) . . ? C16 C11 C1 120.5(3) . . ? C12 C11 C1 120.3(3) . . ? C13 C12 C11 120.4(3) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? O13 C13 C12 123.5(3) . . ? O13 C13 C14 115.8(3) . . ? C12 C13 C14 120.7(3) . . ? O14 C14 C13 119.0(3) . . ? O14 C14 C15 121.9(3) . . ? C13 C14 C15 118.9(3) . . ? O15 C15 C16 124.7(3) . . ? O15 C15 C14 115.2(3) . . ? C16 C15 C14 120.1(3) . . ? C11 C16 C15 120.6(3) . . ? C11 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? O13 C17 H17A 109.5 . . ? O13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O14 C18 H18A 109.5 . . ? O14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O15 C19 H19A 109.5 . . ? O15 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O15 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C33 C31 C34 112.0(3) . . ? C33 C31 C32 110.1(3) . . ? C34 C31 C32 110.7(3) . . ? C33 C31 S31 111.2(2) . . ? C34 C31 S31 108.4(3) . . ? C32 C31 S31 104.1(3) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C3 N31 S31 116.5(2) . . ? C3 N31 H31 115(3) . . ? S31 N31 H31 113(3) . . ? C8 O8 H8 118(3) . . ? C13 O13 C17 116.2(3) . . ? C14 O14 C18 113.5(3) . . ? C15 O15 C19 117.8(3) . . ? O31 S31 N31 111.45(15) . . ? O31 S31 C31 104.19(16) . . ? N31 S31 C31 100.86(15) . . ? 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 C11 C1 C2 C3 -178.8(3) . . . . ? C1 C2 C3 N31 64.5(4) . . . . ? C1 C2 C3 C4 -169.7(3) . . . . ? N31 C3 C4 C9 -104.9(4) . . . . ? C2 C3 C4 C9 132.1(3) . . . . ? N31 C3 C4 C5 75.9(4) . . . . ? C2 C3 C4 C5 -47.1(4) . . . . ? C9 C4 C5 C6 1.4(5) . . . . ? C3 C4 C5 C6 -179.3(3) . . . . ? C4 C5 C6 C7 -1.6(6) . . . . ? C5 C6 C7 C8 1.2(6) . . . . ? C6 C7 C8 O8 -179.2(3) . . . . ? C6 C7 C8 C9 -0.7(5) . . . . ? C5 C4 C9 C8 -0.9(5) . . . . ? C3 C4 C9 C8 179.8(3) . . . . ? O8 C8 C9 C4 179.1(3) . . . . ? C7 C8 C9 C4 0.5(5) . . . . ? C2 C1 C11 C16 -134.4(4) . . . . ? C2 C1 C11 C12 47.3(5) . . . . ? C16 C11 C12 C13 1.4(5) . . . . ? C1 C11 C12 C13 179.7(3) . . . . ? C11 C12 C13 O13 177.3(3) . . . . ? C11 C12 C13 C14 -3.5(5) . . . . ? O13 C13 C14 O14 5.7(4) . . . . ? C12 C13 C14 O14 -173.6(3) . . . . ? O13 C13 C14 C15 -177.8(3) . . . . ? C12 C13 C14 C15 2.9(5) . . . . ? O14 C14 C15 O15 -3.5(5) . . . . ? C13 C14 C15 O15 -179.9(3) . . . . ? O14 C14 C15 C16 176.1(3) . . . . ? C13 C14 C15 C16 -0.3(5) . . . . ? C12 C11 C16 C15 1.2(5) . . . . ? C1 C11 C16 C15 -177.1(3) . . . . ? O15 C15 C16 C11 177.8(4) . . . . ? C14 C15 C16 C11 -1.7(5) . . . . ? C4 C3 N31 S31 86.3(3) . . . . ? C2 C3 N31 S31 -148.8(2) . . . . ? C12 C13 O13 C17 3.0(5) . . . . ? C14 C13 O13 C17 -176.2(3) . . . . ? C13 C14 O14 C18 -109.6(3) . . . . ? C15 C14 O14 C18 74.0(4) . . . . ? C16 C15 O15 C19 2.3(6) . . . . ? C14 C15 O15 C19 -178.2(4) . . . . ? C3 N31 S31 O31 -88.7(3) . . . . ? C3 N31 S31 C31 161.2(3) . . . . ? C33 C31 S31 O31 -50.3(3) . . . . ? C34 C31 S31 O31 -173.9(2) . . . . ? C32 C31 S31 O31 68.2(3) . . . . ? C33 C31 S31 N31 65.3(3) . . . . ? C34 C31 S31 N31 -58.3(3) . . . . ? C32 C31 S31 N31 -176.1(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.802 _refine_diff_density_min -0.629 _refine_diff_density_rms 0.074 # Attachment 'B603857C Figure 2.CIF' data_kj18 _database_code_depnum_ccdc_archive 'CCDC 601951' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H42 B N O7, H2 O' _chemical_formula_sum 'C25 H44 B N O8' _chemical_formula_weight 497.42 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' '-x, -y, z+1/2' _cell_length_a 13.3627(3) _cell_length_b 15.6068(3) _cell_length_c 27.3395(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5701.6(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 73652 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2160 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29479 _diffrn_reflns_av_R_equivalents 0.0604 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5715 _reflns_number_gt 4514 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2004)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction ; DENZO-SMN and COLLECT (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 Altomare, A.; Burla, M. C.; Camalli, G.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Polidori, G. J. Appl. Cryst. 1994, 27, 435-436. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-III Version 1.08 (Farrugia, 2005) ; _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; The structure solved in space group P c a 21 with two molecules of the title compound and two molecules of water in the asymmetric unit. Both molecules have the same numbering scheme and are distinguished with the suffixes A and B. All hydrogen atoms attached to carbon were placed in calculated positions and refined using a riding model. C-H distances: CH3, 0.98\A; CH2, 0.99\A; C-H, 1.00\A; aromatic, 0.95\A. All carbon Uiso(H) values were constrained to be 1.2 times Ueq of the parent atom. Hydrogens in the water molecules were located in the Fourier difference map. Those attached to O1S were refined freely whereas those attached to O2S were constrained to have bond lengths of 1.00\A. In the absence of significant anomalous scattering effects, the absolute configuration could not be confirmed from the diffraction data and Friedel pairs were merged. C. Kilner 20 December 2005 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^)+(0.0519P)^2^+0.4241P] 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_number_reflns 5715 _refine_ls_number_parameters 669 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _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 C1A C 1.0423(2) 0.68934(16) 0.63663(12) 0.0280(7) Uani 1 1 d . . . H1A H 1.1047 0.6941 0.6567 0.034 Uiso 1 1 calc R . . C1B C 0.7499(2) 0.19392(15) 0.73591(12) 0.0258(7) Uani 1 1 d . . . H1B H 0.6908 0.2044 0.7142 0.031 Uiso 1 1 calc R . . C3B C 0.7094(2) 0.40014(17) 0.79196(14) 0.0357(8) Uani 1 1 d . . . C3A C 1.0946(2) 0.89294(17) 0.57923(12) 0.0308(7) Uani 1 1 d . . . C4B C 0.8039(2) 0.37666(18) 0.82228(12) 0.0327(7) Uani 1 1 d . . . C4A C 0.9992(2) 0.87320(17) 0.54911(13) 0.0315(7) Uani 1 1 d . . . C6A C 1.0697(2) 0.93154(19) 0.62897(13) 0.0367(8) Uani 1 1 d . . . H6AA H 1.0463 0.9906 0.6246 0.044 Uiso 1 1 calc R . . H6AB H 1.1297 0.9313 0.6496 0.044 Uiso 1 1 calc R . . H6AC H 1.0170 0.8975 0.6447 0.044 Uiso 1 1 calc R . . C6B C 0.7356(3) 0.43693(19) 0.74204(14) 0.0430(9) Uani 1 1 d . . . H6D H 0.7644 0.4942 0.7461 0.052 Uiso 1 1 calc R . . H6E H 0.6749 0.4407 0.7220 0.052 Uiso 1 1 calc R . . H6F H 0.7843 0.3995 0.7258 0.052 Uiso 1 1 calc R . . C7A C 1.1716(2) 0.94877(19) 0.55337(15) 0.0423(9) Uani 1 1 d . . . H7AA H 1.1418 1.0045 0.5457 0.051 Uiso 1 1 calc R . . H7AB H 1.1929 0.9207 0.5230 0.051 Uiso 1 1 calc R . . H7AC H 1.2296 0.9570 0.5748 0.051 Uiso 1 1 calc R . . C7B C 0.6356(3) 0.4591(2) 0.81805(17) 0.0512(10) Uani 1 1 d . . . H7BA H 0.6679 0.5142 0.8249 0.061 Uiso 1 1 calc R . . H7BB H 0.6145 0.4327 0.8489 0.061 Uiso 1 1 calc R . . H7BC H 0.5770 0.4684 0.7972 0.061 Uiso 1 1 calc R . . C8B C 0.8898(3) 0.44054(19) 0.81904(14) 0.0421(9) Uani 1 1 d . . . H8BA H 0.8688 0.4954 0.8332 0.051 Uiso 1 1 calc R . . H8BB H 0.9083 0.4489 0.7847 0.051 Uiso 1 1 calc R . . H8BF H 0.9475 0.4184 0.8372 0.051 Uiso 1 1 calc R . . C8A C 0.9178(2) 0.94070(19) 0.55274(15) 0.0405(8) Uani 1 1 d . . . H8AA H 0.9431 0.9953 0.5400 0.049 Uiso 1 1 calc R . . H8AB H 0.8983 0.9479 0.5870 0.049 Uiso 1 1 calc R . . H8AC H 0.8596 0.9226 0.5335 0.049 Uiso 1 1 calc R . . C9A C 1.0212(3) 0.8523(2) 0.49588(13) 0.0415(8) Uani 1 1 d . . . H9AA H 1.0410 0.9047 0.4787 0.050 Uiso 1 1 calc R . . H9AB H 0.9611 0.8284 0.4805 0.050 Uiso 1 1 calc R . . H9AC H 1.0756 0.8104 0.4941 0.050 Uiso 1 1 calc R . . C9B C 0.7810(3) 0.3576(2) 0.87585(13) 0.0466(9) Uani 1 1 d . . . H9BA H 0.7654 0.4112 0.8929 0.056 Uiso 1 1 calc R . . H9BB H 0.8394 0.3307 0.8911 0.056 Uiso 1 1 calc R . . H9BC H 0.7235 0.3188 0.8779 0.056 Uiso 1 1 calc R . . C12B C 0.7257(2) 0.10768(17) 0.80282(11) 0.0285(7) Uani 1 1 d . . . C12A C 1.0543(2) 0.60124(17) 0.56967(12) 0.0285(7) Uani 1 1 d . . . C14A C 1.0679(3) 0.52736(18) 0.49187(12) 0.0350(8) Uani 1 1 d . . . H14A H 1.0866 0.5868 0.4816 0.042 Uiso 1 1 calc R . . C14B C 0.7236(3) -0.04976(17) 0.80191(13) 0.0437(9) Uani 1 1 d . . . H14B H 0.7159 -0.0941 0.8281 0.052 Uiso 1 1 calc R . . C15A C 0.9708(3) 0.5044(3) 0.46619(15) 0.0570(11) Uani 1 1 d . . . H15A H 0.9802 0.5083 0.4307 0.068 Uiso 1 1 calc R . . H15B H 0.9181 0.5443 0.4763 0.068 Uiso 1 1 calc R . . H15C H 0.9514 0.4458 0.4749 0.068 Uiso 1 1 calc R . . C15B C 0.6362(3) -0.0633(2) 0.76657(14) 0.0533(10) Uani 1 1 d . . . H15D H 0.6376 -0.1222 0.7542 0.064 Uiso 1 1 calc R . . H15E H 0.6421 -0.0232 0.7391 0.064 Uiso 1 1 calc R . . H15F H 0.5729 -0.0532 0.7838 0.064 Uiso 1 1 calc R . . C16A C 1.1534(3) 0.4684(2) 0.47778(14) 0.0505(9) Uani 1 1 d . . . H16A H 1.1656 0.4727 0.4425 0.061 Uiso 1 1 calc R . . H16B H 1.1359 0.4092 0.4861 0.061 Uiso 1 1 calc R . . H16C H 1.2140 0.4851 0.4956 0.061 Uiso 1 1 calc R . . C16B C 0.8236(3) -0.0660(2) 0.77864(17) 0.0610(11) Uani 1 1 d . . . H16D H 0.8274 -0.1259 0.7679 0.073 Uiso 1 1 calc R . . H16E H 0.8768 -0.0547 0.8025 0.073 Uiso 1 1 calc R . . H16F H 0.8320 -0.0282 0.7503 0.073 Uiso 1 1 calc R . . C17B C 0.7034(3) 0.0374(2) 0.88110(13) 0.0470(9) Uani 1 1 d . . . H17B H 0.7024 0.0990 0.8913 0.056 Uiso 1 1 calc R . . C17A C 1.0311(3) 0.44527(19) 0.57109(14) 0.0509(11) Uani 1 1 d . . . H17A H 1.0323 0.4000 0.5452 0.061 Uiso 1 1 calc R . . C18A C 0.9265(4) 0.4438(3) 0.59292(19) 0.0825(17) Uani 1 1 d . . . H18A H 0.9091 0.3849 0.6022 0.099 Uiso 1 1 calc R . . H18B H 0.8783 0.4649 0.5687 0.099 Uiso 1 1 calc R . . H18C H 0.9246 0.4805 0.6220 0.099 Uiso 1 1 calc R . . C18B C 0.7927(4) -0.0046(3) 0.90594(18) 0.0927(18) Uani 1 1 d . . . H18D H 0.7850 -0.0007 0.9415 0.111 Uiso 1 1 calc R . . H18E H 0.8543 0.0248 0.8961 0.111 Uiso 1 1 calc R . . H18F H 0.7964 -0.0650 0.8962 0.111 Uiso 1 1 calc R . . C19B C 0.6040(4) -0.0010(3) 0.89519(17) 0.0951(19) Uani 1 1 d . . . H19D H 0.5958 0.0019 0.9308 0.114 Uiso 1 1 calc R . . H19E H 0.6017 -0.0610 0.8846 0.114 Uiso 1 1 calc R . . H19F H 0.5499 0.0310 0.8793 0.114 Uiso 1 1 calc R . . C19A C 1.1130(4) 0.4224(2) 0.60727(14) 0.0761(15) Uani 1 1 d . . . H19A H 1.1001 0.3653 0.6208 0.091 Uiso 1 1 calc R . . H19B H 1.1139 0.4646 0.6338 0.091 Uiso 1 1 calc R . . H19C H 1.1778 0.4225 0.5905 0.091 Uiso 1 1 calc R . . C21A C 0.9531(2) 0.70361(18) 0.66951(12) 0.0298(7) Uani 1 1 d . . . H21A H 0.8915 0.7011 0.6494 0.036 Uiso 1 1 calc R . . H21B H 0.9575 0.7619 0.6836 0.036 Uiso 1 1 calc R . . C21B C 0.8439(2) 0.20034(18) 0.70602(11) 0.0288(7) Uani 1 1 d . . . H21C H 0.9019 0.1930 0.7281 0.035 Uiso 1 1 calc R . . H21D H 0.8479 0.2588 0.6921 0.035 Uiso 1 1 calc R . . C22A C 0.9437(2) 0.63858(19) 0.71152(12) 0.0322(7) Uani 1 1 d . . . H22A H 0.9188 0.5835 0.6982 0.039 Uiso 1 1 calc R . . H22B H 1.0108 0.6282 0.7257 0.039 Uiso 1 1 calc R . . C22B C 0.8531(2) 0.13573(18) 0.66425(11) 0.0298(7) Uani 1 1 d . . . H22C H 0.8752 0.0800 0.6777 0.036 Uiso 1 1 calc R . . H22D H 0.7865 0.1273 0.6492 0.036 Uiso 1 1 calc R . . C23A C 0.8739(2) 0.66849(17) 0.75157(11) 0.0274(7) Uani 1 1 d . . . C23B C 0.9265(2) 0.16407(17) 0.62515(11) 0.0275(7) Uani 1 1 d . . . C24A C 0.9134(2) 0.69628(17) 0.79560(12) 0.0299(7) Uani 1 1 d . . . H24A H 0.9838 0.6962 0.8004 0.036 Uiso 1 1 calc R . . C24B C 1.0291(2) 0.15932(17) 0.63278(11) 0.0274(7) Uani 1 1 d . . . H24B H 1.0545 0.1372 0.6627 0.033 Uiso 1 1 calc R . . C25B C 1.0946(2) 0.18706(16) 0.59654(12) 0.0268(7) Uani 1 1 d . . . C25A C 0.8505(2) 0.72423(19) 0.83282(12) 0.0322(7) Uani 1 1 d . . . C26A C 0.7469(2) 0.72446(17) 0.82629(12) 0.0295(7) Uani 1 1 d . . . C26B C 1.0572(2) 0.21964(17) 0.55307(11) 0.0288(7) Uani 1 1 d . . . C27A C 0.7077(2) 0.69636(17) 0.78212(12) 0.0292(7) Uani 1 1 d . . . C27B C 0.9541(2) 0.22629(18) 0.54576(11) 0.0290(7) Uani 1 1 d . . . C28B C 0.8895(2) 0.19804(17) 0.58208(12) 0.0299(7) Uani 1 1 d . . . H28B H 0.8192 0.2021 0.5773 0.036 Uiso 1 1 calc R . . C28A C 0.7697(2) 0.66939(16) 0.74458(12) 0.0298(7) Uani 1 1 d . . . H28A H 0.7419 0.6516 0.7142 0.036 Uiso 1 1 calc R . . C35B C 1.2391(3) 0.15039(19) 0.64374(13) 0.0367(8) Uani 1 1 d . . . H35D H 1.3123 0.1535 0.6420 0.044 Uiso 1 1 calc R . . H35E H 1.2184 0.0905 0.6475 0.044 Uiso 1 1 calc R . . H35F H 1.2155 0.1837 0.6719 0.044 Uiso 1 1 calc R . . C35A C 0.9876(3) 0.7455(3) 0.88677(16) 0.0737(14) Uani 1 1 d . . . H35A H 1.0016 0.7640 0.9203 0.088 Uiso 1 1 calc R . . H35B H 1.0249 0.7816 0.8638 0.088 Uiso 1 1 calc R . . H35C H 1.0082 0.6856 0.8827 0.088 Uiso 1 1 calc R . . C36B C 1.1626(3) 0.1825(2) 0.48740(13) 0.0422(8) Uani 1 1 d . . . H36D H 1.2000 0.2074 0.4601 0.051 Uiso 1 1 calc R . . H36E H 1.1077 0.1472 0.4746 0.051 Uiso 1 1 calc R . . H36F H 1.2074 0.1467 0.5071 0.051 Uiso 1 1 calc R . . C36A C 0.6532(3) 0.6909(2) 0.89668(14) 0.0464(9) Uani 1 1 d . . . H36A H 0.6155 0.7177 0.9233 0.056 Uiso 1 1 calc R . . H36B H 0.7122 0.6618 0.9100 0.056 Uiso 1 1 calc R . . H36C H 0.6106 0.6491 0.8799 0.056 Uiso 1 1 calc R . . C37A C 0.5599(3) 0.6655(2) 0.73577(13) 0.0379(8) Uani 1 1 d . . . H37A H 0.4869 0.6681 0.7389 0.046 Uiso 1 1 calc R . . H37B H 0.5807 0.6059 0.7307 0.046 Uiso 1 1 calc R . . H37C H 0.5812 0.7003 0.7078 0.046 Uiso 1 1 calc R . . C37B C 0.8198(3) 0.2703(3) 0.49479(17) 0.0633(12) Uani 1 1 d . . . H37D H 0.8076 0.3034 0.4649 0.076 Uiso 1 1 calc R . . H37E H 0.7893 0.2998 0.5227 0.076 Uiso 1 1 calc R . . H37F H 0.7901 0.2132 0.4914 0.076 Uiso 1 1 calc R . . N13B N 0.7176(2) 0.03510(14) 0.82714(10) 0.0341(6) Uani 1 1 d . . . N13A N 1.0533(2) 0.52804(14) 0.54590(10) 0.0339(6) Uani 1 1 d . . . O1S O 0.8309(2) 0.67184(16) 0.53367(11) 0.0578(8) Uani 1 1 d . . . H1S H 0.872(3) 0.719(3) 0.5456(19) 0.083(14) Uiso 1 1 d . . . H2S H 0.760(4) 0.693(3) 0.539(2) 0.095(16) Uiso 1 1 d . . . O2A O 1.13614(15) 0.80837(11) 0.58724(8) 0.0290(5) Uani 1 1 d . . . O2B O 0.66344(15) 0.31775(11) 0.78497(8) 0.0321(5) Uani 1 1 d . . . O2S O 0.9661(2) 0.17741(18) 0.84493(13) 0.0683(8) Uani 1 1 d D . . H3S H 1.038(3) 0.195(6) 0.840(4) 0.24(5) Uiso 1 1 d D . . H4S H 0.905(8) 0.211(10) 0.834(8) 0.46(10) Uiso 1 1 d D . . O5A O 0.96530(15) 0.79499(12) 0.57317(8) 0.0306(5) Uani 1 1 d . . . O5B O 0.83325(14) 0.29722(12) 0.79849(8) 0.0287(5) Uani 1 1 d . . . O11A O 1.03490(17) 0.60040(12) 0.61695(8) 0.0346(5) Uani 1 1 d . . . O11B O 0.74431(16) 0.10446(11) 0.75567(7) 0.0297(5) Uani 1 1 d . . . O12A O 1.07498(16) 0.67309(11) 0.54984(8) 0.0299(5) Uani 1 1 d . . . O25B O 1.19720(15) 0.18461(13) 0.60000(9) 0.0349(5) Uani 1 1 d . . . O25A O 0.88310(17) 0.75310(15) 0.87722(9) 0.0451(6) Uani 1 1 d . . . O26A O 0.68446(16) 0.75547(12) 0.86256(8) 0.0354(5) Uani 1 1 d . . . O26B O 1.12235(16) 0.24978(12) 0.51723(8) 0.0355(5) Uani 1 1 d . . . O27A O 0.60507(16) 0.69764(13) 0.77942(9) 0.0369(5) Uani 1 1 d . . . O27B O 0.92480(17) 0.26239(14) 0.50255(8) 0.0409(6) Uani 1 1 d . . . O73B O 0.71588(16) 0.18101(11) 0.82294(8) 0.0318(5) Uani 1 1 d . . . B1A B 1.0538(3) 0.74975(19) 0.58856(14) 0.0276(7) Uani 1 1 d . . . B1B B 0.7415(3) 0.2552(2) 0.78365(13) 0.0268(8) Uani 1 1 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 C1A 0.0283(17) 0.0204(13) 0.0353(19) -0.0013(12) 0.0017(14) -0.0008(11) C1B 0.0275(16) 0.0200(13) 0.0300(17) 0.0056(12) 0.0021(13) 0.0018(11) C3B 0.0305(17) 0.0233(14) 0.053(2) -0.0053(14) 0.0072(16) -0.0008(12) C3A 0.0293(17) 0.0222(14) 0.0408(19) 0.0007(13) -0.0018(14) 0.0006(11) C4B 0.0319(18) 0.0288(15) 0.0375(19) -0.0069(13) 0.0069(15) -0.0048(13) C4A 0.0298(17) 0.0236(14) 0.0411(19) 0.0053(14) 0.0008(15) -0.0024(12) C6A 0.0357(18) 0.0255(14) 0.049(2) -0.0045(14) -0.0056(17) 0.0009(13) C6B 0.042(2) 0.0293(15) 0.058(2) 0.0073(16) 0.0001(18) -0.0007(14) C7A 0.0344(19) 0.0304(16) 0.062(3) 0.0107(16) -0.0031(17) -0.0025(13) C7B 0.041(2) 0.0313(16) 0.082(3) -0.0129(17) 0.015(2) 0.0014(14) C8B 0.038(2) 0.0347(16) 0.054(2) -0.0068(16) 0.0018(17) -0.0093(14) C8A 0.0329(19) 0.0330(16) 0.056(2) 0.0101(16) -0.0066(17) 0.0013(13) C9A 0.049(2) 0.0392(17) 0.0360(19) 0.0087(15) -0.0058(17) -0.0032(15) C9B 0.054(2) 0.0457(19) 0.040(2) -0.0103(17) 0.0093(19) -0.0140(16) C12B 0.0300(17) 0.0290(16) 0.0265(18) 0.0002(13) 0.0039(13) -0.0050(12) C12A 0.0282(17) 0.0260(15) 0.0313(19) 0.0015(13) 0.0064(14) 0.0018(12) C14A 0.052(2) 0.0261(14) 0.0268(18) 0.0010(13) 0.0042(15) 0.0010(13) C14B 0.074(3) 0.0219(15) 0.035(2) 0.0021(14) 0.0069(19) -0.0030(15) C15A 0.072(3) 0.058(2) 0.041(2) -0.0045(18) -0.007(2) 0.0016(19) C15B 0.084(3) 0.0369(19) 0.039(2) -0.0053(15) 0.000(2) -0.0196(18) C16A 0.067(3) 0.0455(19) 0.039(2) 0.0022(16) 0.0154(19) 0.0132(17) C16B 0.082(3) 0.0342(18) 0.067(3) 0.0050(19) 0.015(2) 0.0126(18) C17B 0.082(3) 0.0326(17) 0.027(2) 0.0003(14) 0.0060(19) -0.0112(17) C17A 0.096(3) 0.0220(16) 0.034(2) -0.0001(14) 0.022(2) -0.0087(17) C18A 0.130(4) 0.046(2) 0.072(3) -0.015(2) 0.057(3) -0.038(2) C18B 0.152(5) 0.080(3) 0.046(3) -0.001(2) -0.031(3) 0.029(3) C19B 0.146(5) 0.096(3) 0.043(3) -0.012(2) 0.043(3) -0.073(4) C19A 0.163(5) 0.0325(19) 0.033(2) 0.0040(16) 0.003(3) 0.021(2) C21A 0.0314(17) 0.0265(14) 0.0316(18) 0.0021(13) 0.0056(15) 0.0017(12) C21B 0.0305(18) 0.0247(14) 0.0313(18) 0.0012(13) 0.0035(14) -0.0026(12) C22A 0.0311(18) 0.0311(15) 0.0343(19) 0.0010(14) 0.0047(15) 0.0044(13) C22B 0.0319(17) 0.0278(14) 0.0297(18) -0.0013(12) 0.0039(14) -0.0047(12) C23A 0.0310(18) 0.0226(14) 0.0287(17) 0.0050(12) 0.0056(14) 0.0013(12) C23B 0.0335(18) 0.0209(13) 0.0281(17) -0.0034(12) 0.0039(14) -0.0026(12) C24A 0.0254(17) 0.0321(15) 0.0324(18) 0.0007(13) 0.0027(14) 0.0020(12) C24B 0.0313(18) 0.0240(14) 0.0269(17) 0.0013(12) 0.0026(14) -0.0024(12) C25B 0.0281(18) 0.0224(13) 0.0300(17) -0.0045(12) 0.0012(14) -0.0009(11) C25A 0.0354(19) 0.0299(15) 0.0313(18) -0.0001(13) 0.0019(15) 0.0013(13) C26A 0.0323(18) 0.0249(14) 0.0311(19) 0.0020(13) 0.0085(15) 0.0022(12) C26B 0.0344(18) 0.0216(13) 0.0304(18) 0.0010(13) 0.0106(14) -0.0022(12) C27A 0.0259(17) 0.0238(14) 0.0380(19) 0.0027(13) 0.0092(15) -0.0001(11) C27B 0.0326(18) 0.0287(14) 0.0258(17) 0.0017(13) 0.0005(14) 0.0006(12) C28B 0.0274(17) 0.0269(15) 0.036(2) -0.0031(13) 0.0040(14) 0.0013(12) C28A 0.0366(19) 0.0246(14) 0.0281(17) 0.0017(13) 0.0006(15) -0.0021(12) C35B 0.0312(18) 0.0387(17) 0.040(2) -0.0032(15) -0.0051(15) -0.0018(14) C35A 0.041(2) 0.134(4) 0.046(3) -0.032(3) -0.007(2) 0.010(2) C36B 0.048(2) 0.0471(19) 0.0313(19) 0.0041(15) 0.0131(16) 0.0111(15) C36A 0.058(2) 0.050(2) 0.032(2) -0.0014(16) 0.0173(17) -0.0042(17) C37A 0.0336(19) 0.0380(17) 0.042(2) 0.0050(15) -0.0043(16) 0.0031(13) C37B 0.045(3) 0.096(3) 0.049(3) 0.030(2) -0.008(2) 0.000(2) N13B 0.0495(18) 0.0253(12) 0.0274(15) 0.0034(11) 0.0026(13) -0.0061(11) N13A 0.0506(17) 0.0214(12) 0.0297(15) 0.0001(11) 0.0100(13) -0.0024(11) O1S 0.0432(17) 0.0464(14) 0.084(2) -0.0164(14) -0.0038(15) -0.0024(12) O2A 0.0263(11) 0.0203(9) 0.0405(13) 0.0029(9) -0.0009(10) 0.0022(8) O2B 0.0270(12) 0.0234(10) 0.0457(14) -0.0050(10) 0.0074(10) -0.0021(8) O2S 0.057(2) 0.0609(17) 0.087(2) 0.0213(16) -0.0007(17) 0.0034(14) O5A 0.0288(12) 0.0232(10) 0.0397(13) 0.0035(9) 0.0030(10) -0.0025(8) O5B 0.0270(11) 0.0254(10) 0.0335(13) 0.0000(9) 0.0023(10) 0.0005(8) O11A 0.0504(14) 0.0215(10) 0.0319(13) 0.0000(9) 0.0104(10) -0.0001(9) O11B 0.0416(12) 0.0220(9) 0.0254(12) 0.0021(8) 0.0081(10) -0.0021(8) O12A 0.0374(13) 0.0221(10) 0.0302(12) 0.0028(9) 0.0066(10) -0.0002(8) O25B 0.0265(12) 0.0406(12) 0.0376(13) 0.0041(10) 0.0033(11) 0.0004(9) O25A 0.0375(14) 0.0641(15) 0.0337(14) -0.0121(11) -0.0014(11) 0.0049(11) O26A 0.0372(13) 0.0344(11) 0.0346(13) -0.0044(9) 0.0142(11) 0.0033(9) O26B 0.0386(13) 0.0328(11) 0.0350(13) 0.0053(10) 0.0131(11) 0.0001(9) O27A 0.0304(13) 0.0394(11) 0.0410(14) -0.0033(10) 0.0025(11) 0.0022(9) O27B 0.0339(13) 0.0562(13) 0.0327(13) 0.0118(11) 0.0017(11) 0.0029(10) O73B 0.0408(13) 0.0238(10) 0.0308(12) -0.0007(9) 0.0076(10) -0.0038(9) B1A 0.0252(18) 0.0225(15) 0.035(2) -0.0034(14) 0.0013(16) 0.0009(12) B1B 0.0265(18) 0.0287(16) 0.0252(19) 0.0028(14) 0.0072(15) -0.0031(13) _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 C1A O11A 1.492(3) . ? C1A C21A 1.510(4) . ? C1A B1A 1.624(5) . ? C1A H1A 1.0000 . ? C1B O11B 1.499(3) . ? C1B C21B 1.502(4) . ? C1B B1B 1.622(5) . ? C1B H1B 1.0000 . ? C3B O2B 1.438(3) . ? C3B C6B 1.521(5) . ? C3B C7B 1.526(5) . ? C3B C4B 1.554(5) . ? C3A O2A 1.448(3) . ? C3A C7A 1.522(4) . ? C3A C6A 1.524(5) . ? C3A C4A 1.548(4) . ? C4B O5B 1.454(3) . ? C4B C8B 1.523(4) . ? C4B C9B 1.526(5) . ? C4A O5A 1.459(3) . ? C4A C8A 1.517(4) . ? C4A C9A 1.520(5) . ? C6A H6AA 0.9800 . ? C6A H6AB 0.9800 . ? C6A H6AC 0.9800 . ? C6B H6D 0.9800 . ? C6B H6E 0.9800 . ? C6B H6F 0.9800 . ? C7A H7AA 0.9800 . ? C7A H7AB 0.9800 . ? C7A H7AC 0.9800 . ? C7B H7BA 0.9800 . ? C7B H7BB 0.9800 . ? C7B H7BC 0.9800 . ? C8B H8BA 0.9800 . ? C8B H8BB 0.9800 . ? C8B H8BF 0.9800 . ? C8A H8AA 0.9800 . ? C8A H8AB 0.9800 . ? C8A H8AC 0.9800 . ? C9A H9AA 0.9800 . ? C9A H9AB 0.9800 . ? C9A H9AC 0.9800 . ? C9B H9BA 0.9800 . ? C9B H9BB 0.9800 . ? C9B H9BC 0.9800 . ? C12B O73B 1.277(3) . ? C12B O11B 1.314(4) . ? C12B N13B 1.318(4) . ? C12A O12A 1.276(3) . ? C12A N13A 1.315(4) . ? C12A O11A 1.318(4) . ? C14A N13A 1.490(4) . ? C14A C16A 1.517(5) . ? C14A C15A 1.518(5) . ? C14A H14A 1.0000 . ? C14B N13B 1.495(4) . ? C14B C16B 1.502(5) . ? C14B C15B 1.531(5) . ? C14B H14B 1.0000 . ? C15A H15A 0.9800 . ? C15A H15B 0.9800 . ? C15A H15C 0.9800 . ? C15B H15D 0.9800 . ? C15B H15E 0.9800 . ? C15B H15F 0.9800 . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 0.9800 . ? C17B N13B 1.488(4) . ? C17B C19B 1.508(6) . ? C17B C18B 1.522(6) . ? C17B H17B 1.0000 . ? C17A N13A 1.494(4) . ? C17A C19A 1.518(6) . ? C17A C18A 1.520(6) . ? C17A H17A 1.0000 . ? C18A H18A 0.9800 . ? C18A H18B 0.9800 . ? C18A H18C 0.9800 . ? C18B H18D 0.9800 . ? C18B H18E 0.9800 . ? C18B H18F 0.9800 . ? C19B H19D 0.9800 . ? C19B H19E 0.9800 . ? C19B H19F 0.9800 . ? C19A H19A 0.9800 . ? C19A H19B 0.9800 . ? C19A H19C 0.9800 . ? C21A C22A 1.538(4) . ? C21A H21A 0.9900 . ? C21A H21B 0.9900 . ? C21B C22B 1.529(4) . ? C21B H21C 0.9900 . ? C21B H21D 0.9900 . ? C22A C23A 1.513(4) . ? C22A H22A 0.9900 . ? C22A H22B 0.9900 . ? C22B C23B 1.516(4) . ? C22B H22C 0.9900 . ? C22B H22D 0.9900 . ? C23A C24A 1.384(4) . ? C23A C28A 1.405(4) . ? C23B C28B 1.383(5) . ? C23B C24B 1.389(4) . ? C24A C25A 1.390(4) . ? C24A H24A 0.9500 . ? C24B C25B 1.391(4) . ? C24B H24B 0.9500 . ? C25B O25B 1.374(4) . ? C25B C26B 1.386(4) . ? C25A O25A 1.366(4) . ? C25A C26A 1.395(4) . ? C26A O26A 1.383(4) . ? C26A C27A 1.387(5) . ? C26B O26B 1.392(3) . ? C26B C27B 1.396(4) . ? C27A O27A 1.374(4) . ? C27A C28A 1.384(4) . ? C27B O27B 1.366(4) . ? C27B C28B 1.387(4) . ? C28B H28B 0.9500 . ? C28A H28A 0.9500 . ? C35B O25B 1.425(4) . ? C35B H35D 0.9800 . ? C35B H35E 0.9800 . ? C35B H35F 0.9800 . ? C35A O25A 1.426(5) . ? C35A H35A 0.9800 . ? C35A H35B 0.9800 . ? C35A H35C 0.9800 . ? C36B O26B 1.434(4) . ? C36B H36D 0.9800 . ? C36B H36E 0.9800 . ? C36B H36F 0.9800 . ? C36A O26A 1.435(4) . ? C36A H36A 0.9800 . ? C36A H36B 0.9800 . ? C36A H36C 0.9800 . ? C37A O27A 1.428(4) . ? C37A H37A 0.9800 . ? C37A H37B 0.9800 . ? C37A H37C 0.9800 . ? C37B O27B 1.425(4) . ? C37B H37D 0.9800 . ? C37B H37E 0.9800 . ? C37B H37F 0.9800 . ? O1S H1S 0.97(5) . ? O1S H2S 1.02(6) . ? O2A B1A 1.432(4) . ? O2B B1B 1.430(4) . ? O2S H3S 1.01(2) . ? O2S H4S 1.01(2) . ? O5A B1A 1.440(4) . ? O5B B1B 1.448(4) . ? O12A B1A 1.623(4) . ? O73B B1B 1.616(4) . ? 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 O11A C1A C21A 107.4(2) . . ? O11A C1A B1A 104.8(2) . . ? C21A C1A B1A 118.0(2) . . ? O11A C1A H1A 108.8 . . ? C21A C1A H1A 108.8 . . ? B1A C1A H1A 108.8 . . ? O11B C1B C21B 107.4(2) . . ? O11B C1B B1B 104.8(2) . . ? C21B C1B B1B 117.1(2) . . ? O11B C1B H1B 109.1 . . ? C21B C1B H1B 109.1 . . ? B1B C1B H1B 109.1 . . ? O2B C3B C6B 108.4(3) . . ? O2B C3B C7B 109.0(3) . . ? C6B C3B C7B 109.9(3) . . ? O2B C3B C4B 102.0(2) . . ? C6B C3B C4B 112.4(3) . . ? C7B C3B C4B 114.7(3) . . ? O2A C3A C7A 109.4(2) . . ? O2A C3A C6A 108.0(2) . . ? C7A C3A C6A 109.6(3) . . ? O2A C3A C4A 102.4(2) . . ? C7A C3A C4A 115.0(3) . . ? C6A C3A C4A 111.9(3) . . ? O5B C4B C8B 109.2(2) . . ? O5B C4B C9B 108.5(3) . . ? C8B C4B C9B 109.5(3) . . ? O5B C4B C3B 100.5(2) . . ? C8B C4B C3B 115.3(3) . . ? C9B C4B C3B 113.3(3) . . ? O5A C4A C8A 109.2(3) . . ? O5A C4A C9A 108.2(2) . . ? C8A C4A C9A 110.5(3) . . ? O5A C4A C3A 100.5(2) . . ? C8A C4A C3A 114.6(3) . . ? C9A C4A C3A 113.1(3) . . ? C3A C6A H6AA 109.5 . . ? C3A C6A H6AB 109.5 . . ? H6AA C6A H6AB 109.5 . . ? C3A C6A H6AC 109.5 . . ? H6AA C6A H6AC 109.5 . . ? H6AB C6A H6AC 109.5 . . ? C3B C6B H6D 109.5 . . ? C3B C6B H6E 109.5 . . ? H6D C6B H6E 109.5 . . ? C3B C6B H6F 109.5 . . ? H6D C6B H6F 109.5 . . ? H6E C6B H6F 109.5 . . ? C3A C7A H7AA 109.5 . . ? C3A C7A H7AB 109.5 . . ? H7AA C7A H7AB 109.5 . . ? C3A C7A H7AC 109.5 . . ? H7AA C7A H7AC 109.5 . . ? H7AB C7A H7AC 109.5 . . ? C3B C7B H7BA 109.5 . . ? C3B C7B H7BB 109.5 . . ? H7BA C7B H7BB 109.5 . . ? C3B C7B H7BC 109.5 . . ? H7BA C7B H7BC 109.5 . . ? H7BB C7B H7BC 109.5 . . ? C4B C8B H8BA 109.5 . . ? C4B C8B H8BB 109.5 . . ? H8BA C8B H8BB 109.5 . . ? C4B C8B H8BF 109.5 . . ? H8BA C8B H8BF 109.5 . . ? H8BB C8B H8BF 109.5 . . ? C4A C8A H8AA 109.5 . . ? C4A C8A H8AB 109.5 . . ? H8AA C8A H8AB 109.5 . . ? C4A C8A H8AC 109.5 . . ? H8AA C8A H8AC 109.5 . . ? H8AB C8A H8AC 109.5 . . ? C4A C9A H9AA 109.5 . . ? C4A C9A H9AB 109.5 . . ? H9AA C9A H9AB 109.5 . . ? C4A C9A H9AC 109.5 . . ? H9AA C9A H9AC 109.5 . . ? H9AB C9A H9AC 109.5 . . ? C4B C9B H9BA 109.5 . . ? C4B C9B H9BB 109.5 . . ? H9BA C9B H9BB 109.5 . . ? C4B C9B H9BC 109.5 . . ? H9BA C9B H9BC 109.5 . . ? H9BB C9B H9BC 109.5 . . ? O73B C12B O11B 118.5(3) . . ? O73B C12B N13B 123.0(3) . . ? O11B C12B N13B 118.5(3) . . ? O12A C12A N13A 123.8(3) . . ? O12A C12A O11A 117.9(3) . . ? N13A C12A O11A 118.3(3) . . ? N13A C14A C16A 110.8(3) . . ? N13A C14A C15A 110.4(3) . . ? C16A C14A C15A 112.5(3) . . ? N13A C14A H14A 107.7 . . ? C16A C14A H14A 107.7 . . ? C15A C14A H14A 107.7 . . ? N13B C14B C16B 113.2(3) . . ? N13B C14B C15B 111.9(3) . . ? C16B C14B C15B 112.8(3) . . ? N13B C14B H14B 106.1 . . ? C16B C14B H14B 106.1 . . ? C15B C14B H14B 106.1 . . ? C14A C15A H15A 109.5 . . ? C14A C15A H15B 109.5 . . ? H15A C15A H15B 109.5 . . ? C14A C15A H15C 109.5 . . ? H15A C15A H15C 109.5 . . ? H15B C15A H15C 109.5 . . ? C14B C15B H15D 109.5 . . ? C14B C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? C14B C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 109.5 . . ? C14A C16A H16A 109.5 . . ? C14A C16A H16B 109.5 . . ? H16A C16A H16B 109.5 . . ? C14A C16A H16C 109.5 . . ? H16A C16A H16C 109.5 . . ? H16B C16A H16C 109.5 . . ? C14B C16B H16D 109.5 . . ? C14B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? C14B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? N13B C17B C19B 110.8(3) . . ? N13B C17B C18B 109.4(3) . . ? C19B C17B C18B 113.9(4) . . ? N13B C17B H17B 107.5 . . ? C19B C17B H17B 107.5 . . ? C18B C17B H17B 107.5 . . ? N13A C17A C19A 111.1(3) . . ? N13A C17A C18A 112.2(3) . . ? C19A C17A C18A 113.8(4) . . ? N13A C17A H17A 106.4 . . ? C19A C17A H17A 106.4 . . ? C18A C17A H17A 106.4 . . ? C17A C18A H18A 109.5 . . ? C17A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C17A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C17B C18B H18D 109.5 . . ? C17B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C17B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C17B C19B H19D 109.5 . . ? C17B C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C17B C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? C17A C19A H19A 109.5 . . ? C17A C19A H19B 109.5 . . ? H19A C19A H19B 109.5 . . ? C17A C19A H19C 109.5 . . ? H19A C19A H19C 109.5 . . ? H19B C19A H19C 109.5 . . ? C1A C21A C22A 114.3(2) . . ? C1A C21A H21A 108.7 . . ? C22A C21A H21A 108.7 . . ? C1A C21A H21B 108.7 . . ? C22A C21A H21B 108.7 . . ? H21A C21A H21B 107.6 . . ? C1B C21B C22B 115.5(2) . . ? C1B C21B H21C 108.4 . . ? C22B C21B H21C 108.4 . . ? C1B C21B H21D 108.4 . . ? C22B C21B H21D 108.4 . . ? H21C C21B H21D 107.5 . . ? C23A C22A C21A 112.8(2) . . ? C23A C22A H22A 109.0 . . ? C21A C22A H22A 109.0 . . ? C23A C22A H22B 109.0 . . ? C21A C22A H22B 109.0 . . ? H22A C22A H22B 107.8 . . ? C23B C22B C21B 112.8(2) . . ? C23B C22B H22C 109.0 . . ? C21B C22B H22C 109.0 . . ? C23B C22B H22D 109.0 . . ? C21B C22B H22D 109.0 . . ? H22C C22B H22D 107.8 . . ? C24A C23A C28A 119.6(3) . . ? C24A C23A C22A 119.4(3) . . ? C28A C23A C22A 121.1(3) . . ? C28B C23B C24B 120.1(3) . . ? C28B C23B C22B 118.8(3) . . ? C24B C23B C22B 121.1(3) . . ? C23A C24A C25A 120.3(3) . . ? C23A C24A H24A 119.9 . . ? C25A C24A H24A 119.9 . . ? C23B C24B C25B 119.9(3) . . ? C23B C24B H24B 120.1 . . ? C25B C24B H24B 120.1 . . ? O25B C25B C26B 115.4(3) . . ? O25B C25B C24B 124.8(3) . . ? C26B C25B C24B 119.8(3) . . ? O25A C25A C24A 124.1(3) . . ? O25A C25A C26A 115.4(3) . . ? C24A C25A C26A 120.5(3) . . ? O26A C26A C27A 120.4(3) . . ? O26A C26A C25A 120.5(3) . . ? C27A C26A C25A 119.0(3) . . ? C25B C26B O26B 120.1(3) . . ? C25B C26B C27B 120.4(3) . . ? O26B C26B C27B 119.4(3) . . ? O27A C27A C28A 124.2(3) . . ? O27A C27A C26A 114.8(3) . . ? C28A C27A C26A 121.0(3) . . ? O27B C27B C28B 124.9(3) . . ? O27B C27B C26B 115.9(3) . . ? C28B C27B C26B 119.2(3) . . ? C23B C28B C27B 120.6(3) . . ? C23B C28B H28B 119.7 . . ? C27B C28B H28B 119.7 . . ? C27A C28A C23A 119.6(3) . . ? C27A C28A H28A 120.2 . . ? C23A C28A H28A 120.2 . . ? O25B C35B H35D 109.5 . . ? O25B C35B H35E 109.5 . . ? H35D C35B H35E 109.5 . . ? O25B C35B H35F 109.5 . . ? H35D C35B H35F 109.5 . . ? H35E C35B H35F 109.5 . . ? O25A C35A H35A 109.5 . . ? O25A C35A H35B 109.5 . . ? H35A C35A H35B 109.5 . . ? O25A C35A H35C 109.5 . . ? H35A C35A H35C 109.5 . . ? H35B C35A H35C 109.5 . . ? O26B C36B H36D 109.5 . . ? O26B C36B H36E 109.5 . . ? H36D C36B H36E 109.5 . . ? O26B C36B H36F 109.5 . . ? H36D C36B H36F 109.5 . . ? H36E C36B H36F 109.5 . . ? O26A C36A H36A 109.5 . . ? O26A C36A H36B 109.5 . . ? H36A C36A H36B 109.5 . . ? O26A C36A H36C 109.5 . . ? H36A C36A H36C 109.5 . . ? H36B C36A H36C 109.5 . . ? O27A C37A H37A 109.5 . . ? O27A C37A H37B 109.5 . . ? H37A C37A H37B 109.5 . . ? O27A C37A H37C 109.5 . . ? H37A C37A H37C 109.5 . . ? H37B C37A H37C 109.5 . . ? O27B C37B H37D 109.5 . . ? O27B C37B H37E 109.5 . . ? H37D C37B H37E 109.5 . . ? O27B C37B H37F 109.5 . . ? H37D C37B H37F 109.5 . . ? H37E C37B H37F 109.5 . . ? C12B N13B C17B 119.3(2) . . ? C12B N13B C14B 121.6(3) . . ? C17B N13B C14B 119.1(2) . . ? C12A N13A C14A 119.7(2) . . ? C12A N13A C17A 121.7(3) . . ? C14A N13A C17A 118.5(2) . . ? H1S O1S H2S 103(4) . . ? B1A O2A C3A 107.0(2) . . ? B1B O2B C3B 107.6(2) . . ? H3S O2S H4S 126(10) . . ? B1A O5A C4A 106.7(2) . . ? B1B O5B C4B 106.4(2) . . ? C12A O11A C1A 109.3(2) . . ? C12B O11B C1B 109.1(2) . . ? C12A O12A B1A 109.4(2) . . ? C25B O25B C35B 117.4(2) . . ? C25A O25A C35A 116.6(3) . . ? C26A O26A C36A 113.3(2) . . ? C26B O26B C36B 112.7(2) . . ? C27A O27A C37A 117.5(3) . . ? C27B O27B C37B 116.5(3) . . ? C12B O73B B1B 109.5(2) . . ? O2A B1A O5A 108.1(2) . . ? O2A B1A O12A 108.7(2) . . ? O5A B1A O12A 108.3(3) . . ? O2A B1A C1A 117.6(3) . . ? O5A B1A C1A 116.3(3) . . ? O12A B1A C1A 96.7(2) . . ? O2B B1B O5B 107.5(2) . . ? O2B B1B O73B 108.5(2) . . ? O5B B1B O73B 108.5(2) . . ? O2B B1B C1B 118.2(3) . . ? O5B B1B C1B 115.8(3) . . ? O73B B1B C1B 97.3(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 O2B C3B C4B O5B 39.3(3) . . . . ? C6B C3B C4B O5B -76.6(3) . . . . ? C7B C3B C4B O5B 156.9(3) . . . . ? O2B C3B C4B C8B 156.5(3) . . . . ? C6B C3B C4B C8B 40.6(4) . . . . ? C7B C3B C4B C8B -85.9(4) . . . . ? O2B C3B C4B C9B -76.2(3) . . . . ? C6B C3B C4B C9B 167.9(3) . . . . ? C7B C3B C4B C9B 41.4(3) . . . . ? O2A C3A C4A O5A 38.6(3) . . . . ? C7A C3A C4A O5A 157.2(2) . . . . ? C6A C3A C4A O5A -76.8(3) . . . . ? O2A C3A C4A C8A 155.5(3) . . . . ? C7A C3A C4A C8A -85.9(3) . . . . ? C6A C3A C4A C8A 40.1(4) . . . . ? O2A C3A C4A C9A -76.6(3) . . . . ? C7A C3A C4A C9A 42.1(3) . . . . ? C6A C3A C4A C9A 168.0(2) . . . . ? O11A C1A C21A C22A 57.0(3) . . . . ? B1A C1A C21A C22A 175.0(3) . . . . ? O11B C1B C21B C22B 56.9(3) . . . . ? B1B C1B C21B C22B 174.4(3) . . . . ? C1A C21A C22A C23A 163.2(3) . . . . ? C1B C21B C22B C23B 159.0(3) . . . . ? C21A C22A C23A C24A -106.0(3) . . . . ? C21A C22A C23A C28A 73.3(4) . . . . ? C21B C22B C23B C28B -102.0(3) . . . . ? C21B C22B C23B C24B 75.6(3) . . . . ? C28A C23A C24A C25A 0.5(4) . . . . ? C22A C23A C24A C25A 179.8(3) . . . . ? C28B C23B C24B C25B -1.4(4) . . . . ? C22B C23B C24B C25B -179.0(2) . . . . ? C23B C24B C25B O25B -179.4(2) . . . . ? C23B C24B C25B C26B 0.3(4) . . . . ? C23A C24A C25A O25A -179.6(3) . . . . ? C23A C24A C25A C26A 0.1(4) . . . . ? O25A C25A C26A O26A 2.4(4) . . . . ? C24A C25A C26A O26A -177.4(3) . . . . ? O25A C25A C26A C27A 179.8(2) . . . . ? C24A C25A C26A C27A 0.0(4) . . . . ? O25B C25B C26B O26B -2.2(4) . . . . ? C24B C25B C26B O26B 178.2(2) . . . . ? O25B C25B C26B C27B -179.1(2) . . . . ? C24B C25B C26B C27B 1.2(4) . . . . ? O26A C26A C27A O27A -3.6(4) . . . . ? C25A C26A C27A O27A 179.0(2) . . . . ? O26A C26A C27A C28A 176.6(2) . . . . ? C25A C26A C27A C28A -0.8(4) . . . . ? C25B C26B C27B O27B 177.4(2) . . . . ? O26B C26B C27B O27B 0.5(4) . . . . ? C25B C26B C27B C28B -1.5(4) . . . . ? O26B C26B C27B C28B -178.5(2) . . . . ? C24B C23B C28B C27B 1.1(4) . . . . ? C22B C23B C28B C27B 178.7(3) . . . . ? O27B C27B C28B C23B -178.5(3) . . . . ? C26B C27B C28B C23B 0.3(4) . . . . ? O27A C27A C28A C23A -178.3(2) . . . . ? C26A C27A C28A C23A 1.5(4) . . . . ? C24A C23A C28A C27A -1.3(4) . . . . ? C22A C23A C28A C27A 179.4(3) . . . . ? O73B C12B N13B C17B -4.4(5) . . . . ? O11B C12B N13B C17B 175.9(3) . . . . ? O73B C12B N13B C14B 176.4(3) . . . . ? O11B C12B N13B C14B -3.3(5) . . . . ? C19B C17B N13B C12B 117.0(4) . . . . ? C18B C17B N13B C12B -116.6(4) . . . . ? C19B C17B N13B C14B -63.8(5) . . . . ? C18B C17B N13B C14B 62.6(4) . . . . ? C16B C14B N13B C12B 63.6(4) . . . . ? C15B C14B N13B C12B -65.2(4) . . . . ? C16B C14B N13B C17B -115.5(3) . . . . ? C15B C14B N13B C17B 115.7(3) . . . . ? O12A C12A N13A C14A -5.8(5) . . . . ? O11A C12A N13A C14A 175.8(3) . . . . ? O12A C12A N13A C17A 178.4(3) . . . . ? O11A C12A N13A C17A 0.0(4) . . . . ? C16A C14A N13A C12A 125.4(3) . . . . ? C15A C14A N13A C12A -109.3(3) . . . . ? C16A C14A N13A C17A -58.7(4) . . . . ? C15A C14A N13A C17A 66.6(4) . . . . ? C19A C17A N13A C12A -66.7(4) . . . . ? C18A C17A N13A C12A 62.0(5) . . . . ? C19A C17A N13A C14A 117.5(3) . . . . ? C18A C17A N13A C14A -113.9(4) . . . . ? C7A C3A O2A B1A -152.5(3) . . . . ? C6A C3A O2A B1A 88.2(3) . . . . ? C4A C3A O2A B1A -30.0(3) . . . . ? C6B C3B O2B B1B 88.2(3) . . . . ? C7B C3B O2B B1B -152.2(3) . . . . ? C4B C3B O2B B1B -30.5(3) . . . . ? C8A C4A O5A B1A -154.3(3) . . . . ? C9A C4A O5A B1A 85.4(3) . . . . ? C3A C4A O5A B1A -33.4(3) . . . . ? C8B C4B O5B B1B -155.6(3) . . . . ? C9B C4B O5B B1B 85.0(3) . . . . ? C3B C4B O5B B1B -34.0(3) . . . . ? O12A C12A O11A C1A 0.1(4) . . . . ? N13A C12A O11A C1A 178.7(3) . . . . ? C21A C1A O11A C12A 135.1(3) . . . . ? B1A C1A O11A C12A 8.8(3) . . . . ? O73B C12B O11B C1B 0.1(4) . . . . ? N13B C12B O11B C1B 179.8(3) . . . . ? C21B C1B O11B C12B 131.0(3) . . . . ? B1B C1B O11B C12B 5.7(3) . . . . ? N13A C12A O12A B1A 172.3(3) . . . . ? O11A C12A O12A B1A -9.3(4) . . . . ? C26B C25B O25B C35B -179.1(2) . . . . ? C24B C25B O25B C35B 0.6(4) . . . . ? C24A C25A O25A C35A -6.4(5) . . . . ? C26A C25A O25A C35A 173.8(3) . . . . ? C27A C26A O26A C36A 92.4(3) . . . . ? C25A C26A O26A C36A -90.2(3) . . . . ? C25B C26B O26B C36B 82.0(3) . . . . ? C27B C26B O26B C36B -101.0(3) . . . . ? C28A C27A O27A C37A 2.9(4) . . . . ? C26A C27A O27A C37A -177.0(2) . . . . ? C28B C27B O27B C37B -0.6(5) . . . . ? C26B C27B O27B C37B -179.4(3) . . . . ? O11B C12B O73B B1B -6.0(4) . . . . ? N13B C12B O73B B1B 174.3(3) . . . . ? C3A O2A B1A O5A 9.8(3) . . . . ? C3A O2A B1A O12A 127.1(2) . . . . ? C3A O2A B1A C1A -124.5(3) . . . . ? C4A O5A B1A O2A 16.3(3) . . . . ? C4A O5A B1A O12A -101.3(3) . . . . ? C4A O5A B1A C1A 151.2(3) . . . . ? C12A O12A B1A O2A 135.1(3) . . . . ? C12A O12A B1A O5A -107.7(3) . . . . ? C12A O12A B1A C1A 12.9(3) . . . . ? O11A C1A B1A O2A -127.3(3) . . . . ? C21A C1A B1A O2A 113.4(3) . . . . ? O11A C1A B1A O5A 102.2(3) . . . . ? C21A C1A B1A O5A -17.2(4) . . . . ? O11A C1A B1A O12A -12.1(3) . . . . ? C21A C1A B1A O12A -131.5(3) . . . . ? C3B O2B B1B O5B 10.0(3) . . . . ? C3B O2B B1B O73B 127.2(3) . . . . ? C3B O2B B1B C1B -123.4(3) . . . . ? C4B O5B B1B O2B 16.7(3) . . . . ? C4B O5B B1B O73B -100.5(3) . . . . ? C4B O5B B1B C1B 151.4(3) . . . . ? C12B O73B B1B O2B 131.5(3) . . . . ? C12B O73B B1B O5B -111.9(3) . . . . ? C12B O73B B1B C1B 8.4(3) . . . . ? O11B C1B B1B O2B -123.5(3) . . . . ? C21B C1B B1B O2B 117.6(3) . . . . ? O11B C1B B1B O5B 106.8(3) . . . . ? C21B C1B B1B O5B -12.1(4) . . . . ? O11B C1B B1B O73B -7.9(3) . . . . ? C21B C1B B1B O73B -126.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.158 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.039