# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ic15773 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H29 Br N2 O3' _chemical_formula_weight 485.41 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn 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' '-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 18.7580(18) _cell_length_b 15.0409(14) _cell_length_c 17.1991(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4852.5(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7161 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 22.88 _exptl_crystal_description plate _exptl_crystal_colour light-brown _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 1.722 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4984 _exptl_absorpt_correction_T_max 0.8746 _exptl_absorpt_process_details 'SADABS (BRUKER, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEXCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35835 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_unetI/netI 0.0443 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5580 _reflns_number_gt 4057 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+3.7123P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5580 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 Br1 Br 0.545744(15) 0.60057(2) 0.101588(17) 0.03687(12) Uani 1 1 d . . . O1 O 0.68560(11) 0.71869(14) 0.07863(10) 0.0340(5) Uani 1 1 d . . . H1 H 0.6462 0.6923 0.0835 0.051 Uiso 1 1 d R . . N1 N 0.69483(12) 0.72823(15) 0.36430(12) 0.0256(5) Uani 1 1 d . . . C1 C 0.7500 0.7500 0.4086(2) 0.0286(8) Uani 1 2 d S . . H1A H 0.7500 0.7500 0.4639 0.034 Uiso 1 2 calc SR . . C2 C 0.71508(14) 0.73554(18) 0.28640(14) 0.0235(5) Uani 1 1 d . . . C3 C 0.67827(14) 0.71812(17) 0.21829(14) 0.0238(5) Uani 1 1 d . . . H3 H 0.6306 0.6969 0.2187 0.029 Uiso 1 1 calc R . . C4 C 0.71464(14) 0.73333(17) 0.14988(14) 0.0241(6) Uani 1 1 d . . . C5 C 0.62459(14) 0.70690(19) 0.39285(14) 0.0266(6) Uani 1 1 d . . . C6 C 0.61017(16) 0.6194(2) 0.41209(18) 0.0355(7) Uani 1 1 d . . . C7 C 0.54200(16) 0.6012(2) 0.43964(19) 0.0395(7) Uani 1 1 d . . . H7 H 0.5299 0.5417 0.4525 0.047 Uiso 1 1 calc R . . C8 C 0.49130(15) 0.6673(2) 0.44883(17) 0.0343(7) Uani 1 1 d . . . C9 C 0.50889(16) 0.7532(2) 0.42868(16) 0.0346(7) Uani 1 1 d . . . H9 H 0.4742 0.7987 0.4343 0.042 Uiso 1 1 calc R . . C10 C 0.57577(17) 0.7751(2) 0.40042(15) 0.0317(6) Uani 1 1 d . . . C11 C 0.6651(2) 0.5475(2) 0.4031(2) 0.0583(11) Uani 1 1 d . . . H11A H 0.6919 0.5570 0.3550 0.087 Uiso 1 1 calc R . . H11B H 0.6414 0.4895 0.4011 0.087 Uiso 1 1 calc R . . H11C H 0.6979 0.5491 0.4475 0.087 Uiso 1 1 calc R . . C12 C 0.41753(16) 0.6461(3) 0.4791(2) 0.0462(8) Uani 1 1 d . . . H12A H 0.4158 0.6573 0.5352 0.069 Uiso 1 1 calc R . . H12B H 0.4066 0.5834 0.4689 0.069 Uiso 1 1 calc R . . H12C H 0.3824 0.6838 0.4527 0.069 Uiso 1 1 calc R . . C13 C 0.5943(2) 0.8698(2) 0.3815(2) 0.0471(8) Uani 1 1 d . . . H13A H 0.6261 0.8935 0.4218 0.071 Uiso 1 1 calc R . . H13B H 0.5507 0.9055 0.3795 0.071 Uiso 1 1 calc R . . H13C H 0.6184 0.8722 0.3310 0.071 Uiso 1 1 calc R . . O2 O 0.79074(11) 0.32042(13) 0.52555(10) 0.0321(5) Uani 1 1 d . . . H2 H 0.8234 0.3584 0.5236 0.048 Uiso 1 1 d R . . N2 N 0.78273(11) 0.30978(14) 0.24088(12) 0.0223(5) Uani 1 1 d . . . C14 C 0.7500 0.2500 0.1957(2) 0.0227(7) Uani 1 2 d S . . H14 H 0.7500 0.2500 0.1404 0.027 Uiso 1 2 calc SR . . C15 C 0.77065(13) 0.28788(17) 0.31833(14) 0.0226(5) Uani 1 1 d . . . C16 C 0.79335(14) 0.32848(18) 0.38662(14) 0.0252(6) Uani 1 1 d . . . H16 H 0.8220 0.3805 0.3863 0.030 Uiso 1 1 calc R . . C17 C 0.77173(14) 0.28862(18) 0.45498(15) 0.0257(6) Uani 1 1 d . . . C18 C 0.82572(14) 0.38437(17) 0.21652(14) 0.0238(6) Uani 1 1 d . . . C19 C 0.79203(15) 0.46040(18) 0.18907(16) 0.0293(6) Uani 1 1 d . . . C20 C 0.83583(17) 0.53156(19) 0.17003(18) 0.0365(7) Uani 1 1 d . . . H20 H 0.8150 0.5837 0.1487 0.044 Uiso 1 1 calc R . . C21 C 0.90904(17) 0.5290(2) 0.18114(18) 0.0381(7) Uani 1 1 d . . . C22 C 0.93936(15) 0.4521(2) 0.20950(17) 0.0346(7) Uani 1 1 d . . . H22 H 0.9894 0.4502 0.2176 0.041 Uiso 1 1 calc R . . C23 C 0.89896(15) 0.37720(19) 0.22661(15) 0.0275(6) Uani 1 1 d . . . C24 C 0.71245(17) 0.4663(2) 0.18048(19) 0.0405(7) Uani 1 1 d . . . H24A H 0.6967 0.4254 0.1396 0.061 Uiso 1 1 calc R . . H24B H 0.6991 0.5272 0.1665 0.061 Uiso 1 1 calc R . . H24C H 0.6897 0.4502 0.2298 0.061 Uiso 1 1 calc R . . C25 C 0.9549(2) 0.6089(2) 0.1634(3) 0.0552(10) Uani 1 1 d . . . H25A H 0.9552 0.6490 0.2083 0.083 Uiso 1 1 calc R . . H25B H 0.9356 0.6402 0.1181 0.083 Uiso 1 1 calc R . . H25C H 1.0037 0.5894 0.1522 0.083 Uiso 1 1 calc R . . C26 C 0.93327(15) 0.2924(2) 0.25386(18) 0.0350(7) Uani 1 1 d . . . H26A H 0.9261 0.2859 0.3100 0.052 Uiso 1 1 calc R . . H26B H 0.9844 0.2942 0.2425 0.052 Uiso 1 1 calc R . . H26C H 0.9116 0.2418 0.2268 0.052 Uiso 1 1 calc R . . O3 O 0.89753(11) 0.43139(14) 0.50256(13) 0.0412(5) Uani 1 1 d . . . H3A H 0.9088 0.4748 0.5309 0.062 Uiso 1 1 d R . . H3B H 0.9340 0.4179 0.4769 0.062 Uiso 1 1 d 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 Br1 0.02919(17) 0.0462(2) 0.03526(18) -0.01036(13) -0.00236(12) -0.00005(13) O1 0.0308(11) 0.0550(14) 0.0163(9) -0.0029(8) -0.0026(8) -0.0100(10) N1 0.0233(12) 0.0353(13) 0.0182(11) 0.0004(9) 0.0007(9) -0.0073(10) C1 0.032(2) 0.036(2) 0.0175(17) 0.000 0.000 -0.0056(17) C2 0.0264(13) 0.0279(14) 0.0160(12) -0.0007(10) 0.0019(10) -0.0043(11) C3 0.0222(13) 0.0279(14) 0.0213(12) -0.0013(10) -0.0002(10) -0.0041(11) C4 0.0272(14) 0.0281(14) 0.0169(12) -0.0010(10) -0.0024(10) -0.0013(11) C5 0.0248(13) 0.0396(16) 0.0154(12) -0.0020(11) 0.0024(10) -0.0065(12) C6 0.0317(16) 0.0392(18) 0.0355(16) 0.0020(13) 0.0102(13) -0.0026(13) C7 0.0360(17) 0.0407(18) 0.0418(18) 0.0059(14) 0.0127(14) -0.0079(14) C8 0.0263(15) 0.0490(19) 0.0276(14) -0.0007(13) 0.0043(12) -0.0047(13) C9 0.0317(16) 0.0465(18) 0.0257(14) -0.0028(13) 0.0027(12) 0.0066(14) C10 0.0364(16) 0.0375(17) 0.0211(13) -0.0024(12) -0.0008(11) -0.0037(13) C11 0.050(2) 0.043(2) 0.082(3) 0.0138(19) 0.033(2) 0.0051(17) C12 0.0277(17) 0.066(2) 0.0450(19) 0.0028(17) 0.0113(14) -0.0056(16) C13 0.054(2) 0.0364(18) 0.051(2) -0.0012(15) 0.0121(16) -0.0001(16) O2 0.0387(11) 0.0390(11) 0.0187(9) -0.0038(8) -0.0007(8) -0.0157(9) N2 0.0246(11) 0.0250(11) 0.0174(10) 0.0019(9) 0.0006(8) -0.0032(9) C14 0.0235(18) 0.0266(19) 0.0181(17) 0.000 0.000 0.0011(15) C15 0.0234(13) 0.0263(14) 0.0180(12) 0.0019(10) 0.0010(10) -0.0014(10) C16 0.0281(14) 0.0255(14) 0.0218(13) -0.0002(10) 0.0002(10) -0.0060(11) C17 0.0256(14) 0.0312(15) 0.0202(12) -0.0021(11) -0.0005(10) -0.0036(11) C18 0.0282(14) 0.0252(14) 0.0181(12) -0.0007(10) 0.0029(10) -0.0050(11) C19 0.0325(15) 0.0287(15) 0.0266(14) -0.0038(11) -0.0010(12) 0.0001(12) C20 0.0480(19) 0.0242(15) 0.0374(17) 0.0017(13) 0.0010(14) -0.0013(13) C21 0.0470(19) 0.0316(17) 0.0358(16) -0.0006(13) 0.0108(14) -0.0122(14) C22 0.0272(15) 0.0424(18) 0.0342(16) -0.0016(13) 0.0046(12) -0.0105(13) C23 0.0271(14) 0.0339(16) 0.0215(13) -0.0012(11) 0.0012(11) -0.0028(12) C24 0.0373(17) 0.0357(17) 0.0484(19) -0.0044(14) -0.0067(14) 0.0043(14) C25 0.061(2) 0.039(2) 0.065(2) 0.0002(17) 0.0171(19) -0.0200(18) C26 0.0282(15) 0.0387(17) 0.0380(16) 0.0041(14) 0.0001(12) 0.0028(13) O3 0.0349(12) 0.0429(13) 0.0459(13) -0.0121(10) 0.0103(10) -0.0114(10) _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 C4 1.359(3) . ? O1 H1 0.8434 . ? N1 C1 1.327(3) . ? N1 C2 1.397(3) . ? N1 C5 1.442(3) . ? C1 N1 1.327(3) 2_665 ? C1 H1A 0.9500 . ? C2 C2 1.380(5) 2_665 ? C2 C3 1.385(3) . ? C3 C4 1.379(4) . ? C3 H3 0.9500 . ? C4 C4 1.418(5) 2_665 ? C5 C10 1.381(4) . ? C5 C6 1.383(4) . ? C6 C7 1.391(4) . ? C6 C11 1.502(5) . ? C7 C8 1.385(4) . ? C7 H7 0.9500 . ? C8 C9 1.378(4) . ? C8 C12 1.513(4) . ? C9 C10 1.385(4) . ? C9 H9 0.9500 . ? C10 C13 1.502(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O2 C17 1.352(3) . ? O2 H2 0.8373 . ? N2 C14 1.338(3) . ? N2 C15 1.391(3) . ? N2 C18 1.444(3) . ? C14 N2 1.338(3) 2_655 ? C14 H14 0.9500 . ? C15 C15 1.378(5) 2_655 ? C15 C16 1.390(3) . ? C16 C17 1.381(4) . ? C16 H16 0.9500 . ? C17 C17 1.419(5) 2_655 ? C18 C23 1.389(4) . ? C18 C19 1.389(4) . ? C19 C20 1.389(4) . ? C19 C24 1.503(4) . ? C20 C21 1.387(5) . ? C20 H20 0.9500 . ? C21 C22 1.379(4) . ? C21 C25 1.509(4) . ? C22 C23 1.389(4) . ? C22 H22 0.9500 . ? C23 C26 1.504(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? O3 H3A 0.8417 . ? O3 H3B 0.8392 . ? 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 C4 O1 H1 109.7 . . ? C1 N1 C2 108.6(2) . . ? C1 N1 C5 124.9(2) . . ? C2 N1 C5 126.3(2) . . ? N1 C1 N1 109.8(3) . 2_665 ? N1 C1 H1A 125.1 . . ? N1 C1 H1A 125.1 2_665 . ? C2 C2 C3 122.20(15) 2_665 . ? C2 C2 N1 106.43(14) 2_665 . ? C3 C2 N1 131.4(2) . . ? C4 C3 C2 116.3(2) . . ? C4 C3 H3 121.8 . . ? C2 C3 H3 121.8 . . ? O1 C4 C3 123.0(2) . . ? O1 C4 C4 115.61(14) . 2_665 ? C3 C4 C4 121.42(15) . 2_665 ? C10 C5 C6 123.6(3) . . ? C10 C5 N1 118.2(3) . . ? C6 C5 N1 118.1(3) . . ? C5 C6 C7 116.7(3) . . ? C5 C6 C11 121.7(3) . . ? C7 C6 C11 121.6(3) . . ? C8 C7 C6 121.9(3) . . ? C8 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? C9 C8 C7 118.7(3) . . ? C9 C8 C12 120.2(3) . . ? C7 C8 C12 121.1(3) . . ? C8 C9 C10 121.9(3) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C5 C10 C9 117.2(3) . . ? C5 C10 C13 122.0(3) . . ? C9 C10 C13 120.7(3) . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 O2 H2 113.4 . . ? C14 N2 C15 108.8(2) . . ? C14 N2 C18 127.6(2) . . ? C15 N2 C18 123.6(2) . . ? N2 C14 N2 108.9(3) . 2_655 ? N2 C14 H14 125.5 . . ? N2 C14 H14 125.5 2_655 . ? C15 C15 C16 122.37(15) 2_655 . ? C15 C15 N2 106.70(14) 2_655 . ? C16 C15 N2 130.9(2) . . ? C17 C16 C15 116.0(2) . . ? C17 C16 H16 122.0 . . ? C15 C16 H16 122.0 . . ? O2 C17 C16 122.2(2) . . ? O2 C17 C17 116.16(14) . 2_655 ? C16 C17 C17 121.61(15) . 2_655 ? C23 C18 C19 123.8(2) . . ? C23 C18 N2 117.1(2) . . ? C19 C18 N2 119.0(2) . . ? C20 C19 C18 116.5(3) . . ? C20 C19 C24 121.3(3) . . ? C18 C19 C24 122.3(3) . . ? C21 C20 C19 122.1(3) . . ? C21 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C22 C21 C20 118.7(3) . . ? C22 C21 C25 120.3(3) . . ? C20 C21 C25 120.9(3) . . ? C21 C22 C23 122.0(3) . . ? C21 C22 H22 119.0 . . ? C23 C22 H22 119.0 . . ? C22 C23 C18 116.8(3) . . ? C22 C23 C26 121.3(3) . . ? C18 C23 C26 121.9(2) . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C25 H25A 109.5 . . ? C21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? H3A O3 H3B 106.7 . . ? 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 Br1 0.84 2.36 3.193(2) 171.9 . O2 H2 O3 0.84 1.81 2.637(3) 169.7 . O3 H3A Br1 0.84 2.40 3.242(2) 172.7 8_756 O3 H3B Br1 0.84 2.51 3.342(2) 172.4 4_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.535 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.078 _database_code_depnum_ccdc_archive 'CCDC 950338' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ic15764 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H58.78 B Br N4 O5.61' _chemical_formula_weight 944.35 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' B B 0.0013 0.0007 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8956(2) _cell_length_b 17.9979(4) _cell_length_c 30.9329(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.3726(9) _cell_angle_gamma 90.00 _cell_volume 4952.32(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 27631 _cell_measurement_theta_min 1.31 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour light-brown _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1983 _exptl_absorpt_coefficient_mu 0.882 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.739 _exptl_absorpt_correction_T_max 0.873 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27631 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_unetI/netI 0.0555 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8707 _reflns_number_gt 6133 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (NONIUS, 1998)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997 )' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997 )' _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. The distance restraints (DFIX) were used to the disordered solvents (ethyl acetate and ether). The rigid-bond restraint (DELU) was applied for C33 and C34. To avoid the short inter H...H contact, the intermolecular H...H shortest contact distances were restrained to 2.20\%A. ; _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^)+(0.1046P)^2^+4.6287P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8707 _refine_ls_number_parameters 586 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1956 _refine_ls_wR_factor_gt 0.1788 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.002 _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 Br1 Br 0.98908(5) -0.12156(2) 0.133859(15) 0.04773(18) Uani 1 1 d . . . B1 B 0.4499(6) 0.3689(3) 0.12539(19) 0.0500(13) Uani 1 1 d . . . O1 O 0.4083(3) 0.30164(16) 0.15086(10) 0.0472(7) Uani 1 1 d . . . O2 O 0.5653(3) 0.34153(17) 0.09444(10) 0.0502(8) Uani 1 1 d . . . O3 O 0.3180(4) 0.40275(18) 0.10342(10) 0.0525(8) Uani 1 1 d . . . O4 O 0.5123(3) 0.42861(16) 0.15321(10) 0.0476(8) Uani 1 1 d . . . N1 N 0.6523(4) 0.05564(19) 0.14366(10) 0.0376(8) Uani 1 1 d . . . N2 N 0.8008(4) 0.09324(19) 0.09176(10) 0.0373(8) Uani 1 1 d . . . N3 N 0.1311(4) 0.6600(2) 0.12184(12) 0.0488(10) Uani 1 1 d . . . N4 N 0.3156(4) 0.6848(2) 0.16660(11) 0.0442(9) Uani 1 1 d . . . C1 C 0.7670(4) 0.0360(2) 0.11737(12) 0.0394(10) Uani 1 1 d . . . H1 H 0.8156 -0.0111 0.1172 0.047 Uiso 1 1 calc R . . C2 C 0.4982(4) 0.2452(2) 0.13792(13) 0.0398(10) Uani 1 1 d . . . C3 C 0.5031(4) 0.1753(2) 0.15431(13) 0.0381(9) Uani 1 1 d . . . H3 H 0.4389 0.1588 0.1768 0.046 Uiso 1 1 calc R . . C4 C 0.6125(4) 0.1294(2) 0.13482(13) 0.0361(9) Uani 1 1 d . . . C5 C 0.7060(4) 0.1532(2) 0.10190(13) 0.0378(9) Uani 1 1 d . . . C6 C 0.7001(5) 0.2249(2) 0.08476(13) 0.0416(10) Uani 1 1 d . . . H6 H 0.7637 0.2413 0.0621 0.050 Uiso 1 1 calc R . . C7 C 0.5936(5) 0.2695(2) 0.10363(13) 0.0419(10) Uani 1 1 d . . . C8 C 0.5716(4) 0.0097(2) 0.17454(13) 0.0363(9) Uani 1 1 d . . . C9 C 0.6250(5) 0.0066(3) 0.21706(14) 0.0477(11) Uani 1 1 d . . . C10 C 0.5314(6) -0.0294(3) 0.24659(14) 0.0507(12) Uani 1 1 d . . . H10 H 0.5639 -0.0331 0.2758 0.061 Uiso 1 1 calc R . . C11 C 0.3922(5) -0.0601(2) 0.23516(14) 0.0440(10) Uani 1 1 d . . . C12 C 0.3473(5) -0.0571(2) 0.19201(14) 0.0414(10) Uani 1 1 d . . . H12 H 0.2548 -0.0792 0.1835 0.050 Uiso 1 1 calc R . . C13 C 0.4363(4) -0.0221(2) 0.16097(13) 0.0357(9) Uani 1 1 d . . . C14 C 0.7752(7) 0.0387(4) 0.23000(17) 0.0743(17) Uani 1 1 d . . . H14A H 0.8535 0.0186 0.2112 0.111 Uiso 1 1 calc R . . H14B H 0.7977 0.0253 0.2601 0.111 Uiso 1 1 calc R . . H14C H 0.7721 0.0929 0.2272 0.111 Uiso 1 1 calc R . . C15 C 0.2906(7) -0.0969(3) 0.26817(16) 0.0628(14) Uani 1 1 d . . . H15A H 0.2645 -0.1470 0.2583 0.094 Uiso 1 1 calc R . . H15B H 0.1987 -0.0674 0.2714 0.094 Uiso 1 1 calc R . . H15C H 0.3431 -0.0999 0.2961 0.094 Uiso 1 1 calc R . . C16 C 0.3870(5) -0.0196(3) 0.11427(14) 0.0501(11) Uani 1 1 d . . . H16A H 0.2883 -0.0433 0.1112 0.075 Uiso 1 1 calc R . . H16B H 0.4603 -0.0461 0.0965 0.075 Uiso 1 1 calc R . . H16C H 0.3803 0.0322 0.1047 0.075 Uiso 1 1 calc R . . C17 C 0.9258(5) 0.0980(2) 0.06196(13) 0.0413(10) Uani 1 1 d . . . C18 C 0.8938(5) 0.0910(3) 0.01760(14) 0.0492(11) Uani 1 1 d . . . C19 C 1.0161(6) 0.1001(3) -0.01046(15) 0.0585(13) Uani 1 1 d . . . H19 H 0.9999 0.0946 -0.0407 0.070 Uiso 1 1 calc R . . C20 C 1.1604(6) 0.1167(3) 0.00444(15) 0.0577(14) Uani 1 1 d . . . C21 C 1.1863(5) 0.1248(3) 0.04844(16) 0.0566(13) Uani 1 1 d . . . H21 H 1.2842 0.1370 0.0586 0.068 Uiso 1 1 calc R . . C22 C 1.0687(5) 0.1149(3) 0.07812(14) 0.0495(12) Uani 1 1 d . . . C23 C 0.7370(6) 0.0764(3) 0.00082(16) 0.0676(15) Uani 1 1 d . . . H23A H 0.6872 0.0402 0.0195 0.101 Uiso 1 1 calc R . . H23B H 0.7423 0.0566 -0.0287 0.101 Uiso 1 1 calc R . . H23C H 0.6796 0.1229 0.0007 0.101 Uiso 1 1 calc R . . C24 C 1.2882(7) 0.1273(4) -0.02761(19) 0.0801(19) Uani 1 1 d . . . H24A H 1.3358 0.0792 -0.0334 0.120 Uiso 1 1 calc R . . H24B H 1.3628 0.1615 -0.0154 0.120 Uiso 1 1 calc R . . H24C H 1.2481 0.1478 -0.0547 0.120 Uiso 1 1 calc R . . C25 C 1.0951(6) 0.1222(4) 0.12635(16) 0.078(2) Uani 1 1 d . . . H25A H 1.0109 0.1490 0.1394 0.117 Uiso 1 1 calc R . . H25B H 1.1886 0.1497 0.1316 0.117 Uiso 1 1 calc R . . H25C H 1.1030 0.0726 0.1393 0.117 Uiso 1 1 calc R . . C26 C 0.1925(5) 0.7122(3) 0.14668(14) 0.0475(11) Uani 1 1 d . . . H26 H 0.1552 0.7614 0.1499 0.057 Uiso 1 1 calc R . . C27 C 0.3077(5) 0.4736(2) 0.11663(15) 0.0457(11) Uani 1 1 d . . . C28 C 0.2020(5) 0.5262(3) 0.10484(14) 0.0479(11) Uani 1 1 d . . . H28 H 0.1242 0.5163 0.0845 0.057 Uiso 1 1 calc RD . . C29 C 0.2184(5) 0.5947(3) 0.12518(14) 0.0431(10) Uani 1 1 d . . . C30 C 0.3337(5) 0.6103(2) 0.15363(13) 0.0394(10) Uani 1 1 d . . . C31 C 0.4422(4) 0.5571(2) 0.16610(14) 0.0403(10) Uani 1 1 d . . . H31 H 0.5201 0.5675 0.1864 0.048 Uiso 1 1 calc R . . C32 C 0.4264(4) 0.4898(2) 0.14682(14) 0.0409(10) Uani 1 1 d . . . C33 C -0.0035(6) 0.6647(3) 0.09426(16) 0.0609(13) Uani 1 1 d U . . C34 C 0.0104(8) 0.6941(4) 0.0536(2) 0.0967(16) Uani 1 1 d U . . C35 C -0.1205(9) 0.6918(4) 0.02682(18) 0.093(2) Uani 1 1 d . . . H35 H -0.1144 0.7102 -0.0019 0.112 Uiso 1 1 calc R . . C36 C -0.2551(9) 0.6640(5) 0.0411(3) 0.097(2) Uani 1 1 d . . . C37 C -0.2624(8) 0.6362(5) 0.0819(3) 0.104(3) Uani 1 1 d . . . H37 H -0.3552 0.6166 0.0917 0.125 Uiso 1 1 calc R . . C38 C -0.1389(6) 0.6354(4) 0.1097(2) 0.0797(18) Uani 1 1 d . . . C39 C 0.1587(8) 0.7282(4) 0.0399(2) 0.098(2) Uani 1 1 d . . . H39A H 0.1809 0.7715 0.0581 0.147 Uiso 1 1 calc R . . H39B H 0.1518 0.7437 0.0096 0.147 Uiso 1 1 calc R . . H39C H 0.2391 0.6914 0.0432 0.147 Uiso 1 1 calc R . . C40 C -0.3907(8) 0.6610(4) 0.0109(2) 0.0967(16) Uani 1 1 d . . . H40A H -0.4239 0.6093 0.0077 0.145 Uiso 1 1 calc R . . H40B H -0.3630 0.6809 -0.0174 0.145 Uiso 1 1 calc R . . H40C H -0.4724 0.6908 0.0230 0.145 Uiso 1 1 calc R . . C41 C -0.1530(7) 0.6034(5) 0.1542(2) 0.108(3) Uani 1 1 d . . . H41A H -0.0532 0.5901 0.1652 0.163 Uiso 1 1 calc R . . H41B H -0.2166 0.5590 0.1531 0.163 Uiso 1 1 calc R . . H41C H -0.1986 0.6404 0.1733 0.163 Uiso 1 1 calc R . . C42 C 0.4260(5) 0.7231(2) 0.19263(14) 0.0428(10) Uani 1 1 d . . . C43 C 0.4312(6) 0.7096(3) 0.23689(15) 0.0552(13) Uani 1 1 d . . . C44 C 0.5504(6) 0.7405(3) 0.26004(17) 0.0649(14) Uani 1 1 d . . . H44 H 0.5561 0.7314 0.2903 0.078 Uiso 1 1 calc R . . C45 C 0.6618(6) 0.7839(3) 0.24128(18) 0.0608(13) Uani 1 1 d . . . C46 C 0.6492(6) 0.7977(3) 0.19724(18) 0.0588(13) Uani 1 1 d . . . H46 H 0.7215 0.8286 0.1837 0.071 Uiso 1 1 calc R . . C47 C 0.5333(6) 0.7673(2) 0.17237(15) 0.0520(12) Uani 1 1 d . . . C48 C 0.3138(7) 0.6618(4) 0.25843(18) 0.086(2) Uani 1 1 d . . . H48A H 0.2187 0.6656 0.2424 0.129 Uiso 1 1 calc R . . H48B H 0.2990 0.6789 0.2882 0.129 Uiso 1 1 calc R . . H48C H 0.3475 0.6100 0.2587 0.129 Uiso 1 1 calc R . . C49 C 0.7914(7) 0.8149(4) 0.2673(2) 0.093(2) Uani 1 1 d . . . H49A H 0.7537 0.8515 0.2880 0.139 Uiso 1 1 calc R . . H49B H 0.8632 0.8388 0.2478 0.139 Uiso 1 1 calc R . . H49C H 0.8417 0.7745 0.2829 0.139 Uiso 1 1 calc R . . C50 C 0.5209(8) 0.7835(3) 0.12417(17) 0.085(2) Uani 1 1 d . . . H50A H 0.4364 0.8173 0.1189 0.128 Uiso 1 1 calc R . . H50B H 0.5040 0.7369 0.1084 0.128 Uiso 1 1 calc R . . H50C H 0.6141 0.8066 0.1142 0.128 Uiso 1 1 calc R . . O5 O 0.9198(9) 0.4205(5) 0.1412(3) 0.100 Uiso 0.607(4) 1 d PD A 1 O6 O 0.9022(10) 0.3934(5) 0.0756(3) 0.097(2) Uiso 0.607(4) 1 d P A 1 C51 C 0.9483(15) 0.3771(7) 0.1147(4) 0.093(3) Uiso 0.607(4) 1 d PD A 1 C52 C 1.0375(15) 0.3081(7) 0.1171(5) 0.103(3) Uiso 0.607(4) 1 d P A 1 H52A H 1.0662 0.2984 0.1472 0.155 Uiso 0.607(4) 1 calc PR A 1 H52B H 1.1282 0.3136 0.0995 0.155 Uiso 0.607(4) 1 calc PR A 1 H52C H 0.9773 0.2666 0.1060 0.155 Uiso 0.607(4) 1 calc PR A 1 C53 C 0.8294(10) 0.4563(7) 0.0665(4) 0.094(3) Uiso 0.607(4) 1 d P A 1 H53A H 0.8879 0.4991 0.0776 0.113 Uiso 0.607(4) 1 calc PR A 1 H53B H 0.7306 0.4562 0.0810 0.113 Uiso 0.607(4) 1 calc PR A 1 C54 C 0.8069(17) 0.4643(8) 0.0198(5) 0.111(4) Uiso 0.607(4) 1 d P A 1 H54A H 0.7618 0.5129 0.0136 0.167 Uiso 0.607(4) 1 calc PR A 1 H54B H 0.7400 0.4249 0.0093 0.167 Uiso 0.607(4) 1 calc PR A 1 H54C H 0.9041 0.4606 0.0052 0.167 Uiso 0.607(4) 1 calc PR A 1 O7 O 0.9224(14) 0.3557(7) 0.0514(4) 0.097(2) Uiso 0.393(4) 1 d PD A 2 C55 C 0.966(2) 0.3496(13) 0.1333(5) 0.093(3) Uiso 0.393(4) 1 d PD A 2 H55A H 1.0476 0.3343 0.1530 0.140 Uiso 0.393(4) 1 calc PR A 2 H55B H 0.8770 0.3192 0.1388 0.140 Uiso 0.393(4) 1 calc PR A 2 H55C H 0.9425 0.4020 0.1383 0.140 Uiso 0.393(4) 1 calc PR A 2 C56 C 1.0171(19) 0.3387(12) 0.0858(4) 0.103(3) Uiso 0.393(4) 1 d PD A 2 H56A H 1.1098 0.3684 0.0820 0.124 Uiso 0.393(4) 1 calc PR A 2 H56B H 1.0462 0.2859 0.0826 0.124 Uiso 0.393(4) 1 calc PR A 2 C57 C 0.8967(18) 0.4333(8) 0.0361(6) 0.094(3) Uiso 0.393(4) 1 d PD A 2 H57A H 0.9681 0.4435 0.0124 0.113 Uiso 0.393(4) 1 calc PR A 2 H57B H 0.9214 0.4676 0.0601 0.113 Uiso 0.393(4) 1 calc PR A 2 C58 C 0.732(2) 0.4521(13) 0.0192(8) 0.111(4) Uiso 0.393(4) 1 d PD A 2 H58A H 0.7297 0.5030 0.0081 0.167 Uiso 0.393(4) 1 calc PR A 2 H58B H 0.6610 0.4474 0.0431 0.167 Uiso 0.393(4) 1 calc PR A 2 H58C H 0.7041 0.4174 -0.0039 0.167 Uiso 0.393(4) 1 calc PR A 2 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 Br1 0.0421(3) 0.0437(3) 0.0574(3) 0.0090(2) -0.0023(2) 0.0066(2) B1 0.047(3) 0.048(3) 0.055(3) 0.007(3) 0.011(2) 0.012(3) O1 0.0437(17) 0.0395(16) 0.0585(19) -0.0004(14) 0.0155(14) 0.0106(14) O2 0.0499(18) 0.0459(18) 0.0549(18) 0.0101(15) 0.0173(15) 0.0130(15) O3 0.0482(18) 0.0525(19) 0.0569(19) -0.0013(16) 0.0013(15) 0.0118(15) O4 0.0410(17) 0.0403(17) 0.0613(19) 0.0087(15) 0.0020(15) 0.0145(14) N1 0.0368(18) 0.042(2) 0.0340(18) -0.0022(15) 0.0028(15) 0.0044(16) N2 0.0350(18) 0.0420(19) 0.0350(18) -0.0005(16) 0.0067(15) 0.0076(16) N3 0.042(2) 0.058(2) 0.047(2) 0.017(2) 0.0070(18) 0.0237(19) N4 0.045(2) 0.043(2) 0.044(2) 0.0135(17) 0.0126(17) 0.0194(18) C1 0.038(2) 0.045(2) 0.036(2) -0.0048(19) 0.0021(18) 0.0089(19) C2 0.032(2) 0.043(2) 0.044(2) -0.0009(19) 0.0069(18) 0.0044(19) C3 0.032(2) 0.043(2) 0.040(2) -0.0032(19) 0.0090(18) -0.0005(18) C4 0.032(2) 0.037(2) 0.040(2) -0.0019(18) -0.0001(18) 0.0019(18) C5 0.034(2) 0.042(2) 0.038(2) -0.0014(19) 0.0062(18) 0.0063(19) C6 0.040(2) 0.048(3) 0.038(2) 0.005(2) 0.0106(19) 0.004(2) C7 0.039(2) 0.045(2) 0.042(2) 0.006(2) 0.0049(19) 0.007(2) C8 0.038(2) 0.033(2) 0.038(2) 0.0008(17) 0.0055(18) 0.0040(18) C9 0.053(3) 0.049(3) 0.041(2) -0.006(2) -0.004(2) 0.002(2) C10 0.066(3) 0.057(3) 0.029(2) 0.000(2) 0.002(2) 0.001(3) C11 0.054(3) 0.036(2) 0.041(2) -0.0002(19) 0.010(2) 0.006(2) C12 0.038(2) 0.040(2) 0.046(2) -0.0017(19) 0.0042(19) 0.0029(19) C13 0.037(2) 0.033(2) 0.037(2) 0.0002(17) 0.0017(18) 0.0042(18) C14 0.077(4) 0.091(4) 0.055(3) 0.008(3) -0.020(3) -0.028(3) C15 0.081(4) 0.060(3) 0.048(3) 0.007(2) 0.024(3) 0.003(3) C16 0.050(3) 0.056(3) 0.044(3) 0.007(2) -0.005(2) -0.010(2) C17 0.041(2) 0.048(2) 0.035(2) 0.0004(19) 0.0086(19) 0.015(2) C18 0.053(3) 0.057(3) 0.038(2) -0.002(2) 0.005(2) 0.012(2) C19 0.063(3) 0.077(4) 0.036(2) 0.004(2) 0.011(2) 0.024(3) C20 0.062(3) 0.066(3) 0.046(3) 0.016(2) 0.021(2) 0.025(3) C21 0.039(2) 0.072(3) 0.058(3) 0.007(3) 0.013(2) 0.012(2) C22 0.041(3) 0.070(3) 0.037(2) -0.001(2) 0.008(2) 0.014(2) C23 0.068(4) 0.086(4) 0.049(3) -0.012(3) -0.007(3) 0.006(3) C24 0.066(4) 0.107(5) 0.068(4) 0.029(3) 0.033(3) 0.026(3) C25 0.040(3) 0.149(6) 0.044(3) -0.010(3) 0.000(2) 0.000(3) C26 0.053(3) 0.045(3) 0.045(3) 0.008(2) 0.009(2) 0.019(2) C27 0.042(2) 0.044(3) 0.051(3) 0.005(2) 0.010(2) 0.011(2) C28 0.039(2) 0.062(3) 0.042(2) 0.008(2) -0.001(2) 0.012(2) C29 0.040(2) 0.046(3) 0.043(2) 0.009(2) 0.008(2) 0.015(2) C30 0.038(2) 0.041(2) 0.039(2) 0.0111(19) 0.0095(19) 0.0103(19) C31 0.031(2) 0.043(2) 0.047(2) 0.012(2) 0.0092(18) 0.0100(19) C32 0.032(2) 0.043(3) 0.047(2) 0.013(2) 0.0087(19) 0.0125(19) C33 0.055(3) 0.068(3) 0.060(2) -0.005(2) -0.010(2) 0.036(3) C34 0.096(3) 0.131(4) 0.063(2) 0.012(2) -0.015(2) 0.053(3) C35 0.129(6) 0.107(5) 0.043(3) -0.002(3) -0.015(4) 0.066(5) C36 0.077(5) 0.116(6) 0.098(5) -0.013(5) -0.029(4) 0.048(5) C37 0.060(4) 0.151(7) 0.101(6) 0.015(5) -0.017(4) 0.036(4) C38 0.047(3) 0.116(5) 0.076(4) 0.011(4) -0.005(3) 0.030(3) C39 0.117(6) 0.110(5) 0.069(4) 0.039(4) 0.022(4) 0.051(5) C40 0.096(3) 0.131(4) 0.063(2) 0.012(2) -0.015(2) 0.053(3) C41 0.048(3) 0.184(8) 0.094(5) 0.050(5) 0.011(3) 0.014(4) C42 0.044(2) 0.039(2) 0.045(2) 0.005(2) 0.008(2) 0.013(2) C43 0.055(3) 0.064(3) 0.046(3) 0.018(2) 0.010(2) 0.010(3) C44 0.069(4) 0.075(4) 0.050(3) 0.012(3) -0.005(3) 0.009(3) C45 0.064(3) 0.046(3) 0.073(4) 0.006(3) -0.002(3) 0.008(3) C46 0.063(3) 0.038(3) 0.076(4) 0.000(2) 0.015(3) -0.001(2) C47 0.072(3) 0.033(2) 0.051(3) 0.007(2) 0.025(3) 0.010(2) C48 0.076(4) 0.130(6) 0.050(3) 0.025(3) 0.011(3) -0.023(4) C49 0.086(5) 0.074(4) 0.118(6) 0.005(4) -0.033(4) -0.003(4) C50 0.144(6) 0.060(4) 0.053(3) 0.005(3) 0.032(4) -0.028(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 B1 O4 1.483(7) . ? B1 O3 1.483(6) . ? B1 O1 1.492(6) . ? B1 O2 1.492(6) . ? O1 C2 1.356(5) . ? O2 C7 1.350(5) . ? O3 C27 1.341(5) . ? O4 C32 1.355(5) . ? N1 C1 1.356(5) . ? N1 C4 1.400(5) . ? N1 C8 1.456(5) . ? N2 C1 1.336(5) . ? N2 C5 1.407(5) . ? N2 C17 1.451(5) . ? N3 C26 1.329(6) . ? N3 C29 1.412(6) . ? N3 C33 1.468(6) . ? N4 C26 1.347(6) . ? N4 C30 1.408(5) . ? N4 C42 1.442(6) . ? C1 H1 0.9500 . ? C2 C3 1.356(6) . ? C2 C7 1.431(6) . ? C3 C4 1.415(5) . ? C3 H3 0.9500 . ? C4 C5 1.387(6) . ? C5 C6 1.395(6) . ? C6 C7 1.375(6) . ? C6 H6 0.9500 . ? C8 C13 1.395(6) . ? C8 C9 1.396(6) . ? C9 C10 1.399(6) . ? C9 C14 1.507(7) . ? C10 C11 1.399(6) . ? C10 H10 0.9500 . ? C11 C12 1.392(6) . ? C11 C15 1.520(6) . ? C12 C13 1.398(6) . ? C12 H12 0.9500 . ? C13 C16 1.507(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.397(6) . ? C17 C18 1.405(6) . ? C18 C19 1.406(7) . ? C18 C23 1.509(7) . ? C19 C20 1.393(8) . ? C19 H19 0.9500 . ? C20 C21 1.387(7) . ? C20 C24 1.525(7) . ? C21 C22 1.408(6) . ? C21 H21 0.9500 . ? C22 C25 1.514(7) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26 0.9500 . ? C27 C28 1.382(6) . ? C27 C32 1.435(6) . ? C28 C29 1.392(7) . ? C28 H28 0.9500 . ? C29 C30 1.376(6) . ? C30 C31 1.412(6) . ? C31 C32 1.356(6) . ? C31 H31 0.9500 . ? C33 C34 1.370(8) . ? C33 C38 1.401(8) . ? C34 C35 1.426(9) . ? C34 C39 1.517(10) . ? C35 C36 1.373(11) . ? C35 H35 0.9500 . ? C36 C37 1.359(10) . ? C36 C40 1.521(9) . ? C37 C38 1.392(8) . ? C37 H37 0.9500 . ? C38 C41 1.498(9) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.391(6) . ? C42 C47 1.395(6) . ? C43 C44 1.392(7) . ? C43 C48 1.511(7) . ? C44 C45 1.392(7) . ? C44 H44 0.9500 . ? C45 C46 1.388(7) . ? C45 C49 1.509(8) . ? C46 C47 1.393(7) . ? C46 H46 0.9500 . ? C47 C50 1.522(7) . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? O5 C51 1.160(8) . ? O6 C51 1.308(14) . ? O6 C53 1.333(13) . ? C51 C52 1.476(16) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 C54 1.463(17) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? O7 C56 1.387(9) . ? O7 C57 1.492(9) . ? C55 C56 1.553(10) . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? C57 C58 1.587(10) . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 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 O4 B1 O3 105.1(4) . . ? O4 B1 O1 112.0(4) . . ? O3 B1 O1 112.2(4) . . ? O4 B1 O2 110.8(4) . . ? O3 B1 O2 112.8(4) . . ? O1 B1 O2 104.2(4) . . ? C2 O1 B1 107.6(3) . . ? C7 O2 B1 108.0(3) . . ? C27 O3 B1 107.8(4) . . ? C32 O4 B1 107.2(3) . . ? C1 N1 C4 108.7(3) . . ? C1 N1 C8 128.4(3) . . ? C4 N1 C8 122.8(3) . . ? C1 N2 C5 108.8(3) . . ? C1 N2 C17 126.8(3) . . ? C5 N2 C17 124.0(4) . . ? C26 N3 C29 108.8(4) . . ? C26 N3 C33 128.8(4) . . ? C29 N3 C33 122.4(4) . . ? C26 N4 C30 108.2(4) . . ? C26 N4 C42 129.0(4) . . ? C30 N4 C42 122.4(3) . . ? N2 C1 N1 109.1(4) . . ? N2 C1 H1 125.4 . . ? N1 C1 H1 125.4 . . ? O1 C2 C3 127.0(4) . . ? O1 C2 C7 110.1(4) . . ? C3 C2 C7 122.9(4) . . ? C2 C3 C4 113.8(4) . . ? C2 C3 H3 123.1 . . ? C4 C3 H3 123.1 . . ? C5 C4 N1 106.5(3) . . ? C5 C4 C3 123.3(4) . . ? N1 C4 C3 130.1(4) . . ? C4 C5 C6 122.9(4) . . ? C4 C5 N2 106.9(4) . . ? C6 C5 N2 130.2(4) . . ? C7 C6 C5 113.8(4) . . ? C7 C6 H6 123.1 . . ? C5 C6 H6 123.1 . . ? O2 C7 C6 126.8(4) . . ? O2 C7 C2 109.9(3) . . ? C6 C7 C2 123.3(4) . . ? C13 C8 C9 123.7(4) . . ? C13 C8 N1 117.6(3) . . ? C9 C8 N1 118.3(4) . . ? C8 C9 C10 115.7(4) . . ? C8 C9 C14 122.0(4) . . ? C10 C9 C14 122.3(4) . . ? C9 C10 C11 123.2(4) . . ? C9 C10 H10 118.4 . . ? C11 C10 H10 118.4 . . ? C12 C11 C10 118.3(4) . . ? C12 C11 C15 119.5(4) . . ? C10 C11 C15 122.1(4) . . ? C11 C12 C13 121.1(4) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C8 C13 C12 118.0(4) . . ? C8 C13 C16 121.4(4) . . ? C12 C13 C16 120.6(4) . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 123.1(4) . . ? C22 C17 N2 119.0(4) . . ? C18 C17 N2 117.7(4) . . ? C17 C18 C19 116.1(4) . . ? C17 C18 C23 122.2(4) . . ? C19 C18 C23 121.7(4) . . ? C20 C19 C18 122.4(4) . . ? C20 C19 H19 118.8 . . ? C18 C19 H19 118.8 . . ? C21 C20 C19 119.6(4) . . ? C21 C20 C24 120.3(5) . . ? C19 C20 C24 120.0(5) . . ? C20 C21 C22 120.5(5) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C17 C22 C21 118.2(4) . . ? C17 C22 C25 120.4(4) . . ? C21 C22 C25 121.3(4) . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N3 C26 N4 109.6(4) . . ? N3 C26 H26 125.2 . . ? N4 C26 H26 125.2 . . ? O3 C27 C28 128.2(4) . . ? O3 C27 C32 109.9(4) . . ? C28 C27 C32 121.9(4) . . ? C27 C28 C29 114.8(4) . . ? C27 C28 H28 122.6 . . ? C29 C28 H28 122.6 . . ? C30 C29 C28 123.0(4) . . ? C30 C29 N3 106.5(4) . . ? C28 C29 N3 130.4(4) . . ? C29 C30 N4 106.9(4) . . ? C29 C30 C31 122.8(4) . . ? N4 C30 C31 130.3(4) . . ? C32 C31 C30 114.6(4) . . ? C32 C31 H31 122.7 . . ? C30 C31 H31 122.7 . . ? O4 C32 C31 127.2(4) . . ? O4 C32 C27 109.9(4) . . ? C31 C32 C27 122.8(4) . . ? C34 C33 C38 122.7(5) . . ? C34 C33 N3 118.5(5) . . ? C38 C33 N3 118.7(5) . . ? C33 C34 C35 116.4(7) . . ? C33 C34 C39 119.7(6) . . ? C35 C34 C39 123.9(6) . . ? C36 C35 C34 122.3(6) . . ? C36 C35 H35 118.9 . . ? C34 C35 H35 118.9 . . ? C37 C36 C35 118.7(6) . . ? C37 C36 C40 120.9(8) . . ? C35 C36 C40 120.3(7) . . ? C36 C37 C38 122.4(7) . . ? C36 C37 H37 118.8 . . ? C38 C37 H37 118.8 . . ? C37 C38 C33 117.5(6) . . ? C37 C38 C41 120.1(6) . . ? C33 C38 C41 122.4(5) . . ? C34 C39 H39A 109.5 . . ? C34 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C34 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C36 C40 H40A 109.5 . . ? C36 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C36 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C38 C41 H41A 109.5 . . ? C38 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C38 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C43 C42 C47 121.6(5) . . ? C43 C42 N4 119.0(4) . . ? C47 C42 N4 119.2(4) . . ? C42 C43 C44 117.2(5) . . ? C42 C43 C48 121.0(5) . . ? C44 C43 C48 121.8(4) . . ? C45 C44 C43 123.5(5) . . ? C45 C44 H44 118.3 . . ? C43 C44 H44 118.3 . . ? C46 C45 C44 117.2(5) . . ? C46 C45 C49 120.9(5) . . ? C44 C45 C49 122.0(5) . . ? C45 C46 C47 121.8(5) . . ? C45 C46 H46 119.1 . . ? C47 C46 H46 119.1 . . ? C46 C47 C42 118.8(4) . . ? C46 C47 C50 121.0(5) . . ? C42 C47 C50 120.2(5) . . ? C43 C48 H48A 109.5 . . ? C43 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C43 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C45 C49 H49A 109.5 . . ? C45 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C45 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C47 C50 H50A 109.5 . . ? C47 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C47 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C51 O6 C53 122.4(10) . . ? O5 C51 O6 115.6(12) . . ? O5 C51 C52 130.7(14) . . ? O6 C51 C52 113.5(10) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O6 C53 C54 110.9(11) . . ? O6 C53 H53A 109.5 . . ? C54 C53 H53A 109.5 . . ? O6 C53 H53B 109.5 . . ? C54 C53 H53B 109.5 . . ? H53A C53 H53B 108.0 . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C56 O7 C57 122.8(14) . . ? C56 C55 H55A 109.5 . . ? C56 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C56 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? O7 C56 C55 121.3(15) . . ? O7 C56 H56A 107.0 . . ? C55 C56 H56A 107.0 . . ? O7 C56 H56B 107.0 . . ? C55 C56 H56B 107.0 . . ? H56A C56 H56B 106.7 . . ? O7 C57 C58 116.3(14) . . ? O7 C57 H57A 108.2 . . ? C58 C57 H57A 108.2 . . ? O7 C57 H57B 108.2 . . ? C58 C57 H57B 108.2 . . ? H57A C57 H57B 107.4 . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.800 _refine_diff_density_min -1.079 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 950339' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ic16249 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C63.64 H80.55 B3 K N4 O8.64' _chemical_formula_weight 1111.25 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' B B 0.0013 0.0007 '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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.2188(4) _cell_length_b 19.7828(4) _cell_length_c 16.8614(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.3330(9) _cell_angle_gamma 90.00 _cell_volume 6584.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25445 _cell_measurement_theta_min 1.46 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2374 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.884 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25445 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_unetI/netI 0.0550 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7542 _reflns_number_gt 4712 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _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. The distance restraints (DFIX) were used to the disordered solvents (MeOH) and the rigid-bond restraint (DELU) was used for O3 and C27. The distance restraints (DFIX) and isotropic restraints (ISOR) are applied to the ether. ; _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^)+(0.1819P)^2^+2.2463P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7542 _refine_ls_number_parameters 397 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_gt 0.0811 _refine_ls_wR_factor_ref 0.2823 _refine_ls_wR_factor_gt 0.2483 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.002 _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 K1 K 1.0000 0.40350(6) 0.2500 0.0514(3) Uani 1 2 d S . . O1 O 0.56171(9) 0.25803(10) 0.29516(12) 0.0349(5) Uani 1 1 d . . . O2 O 0.51251(9) 0.34298(10) 0.18733(12) 0.0380(5) Uani 1 1 d . . . N1 N 0.77861(11) 0.29671(11) 0.28378(14) 0.0314(5) Uani 1 1 d . . . N2 N 0.73354(11) 0.37949(11) 0.19023(14) 0.0318(5) Uani 1 1 d . . . B1 B 0.86212(18) 0.3583(2) 0.2356(3) 0.0451(8) Uani 1 1 d . . . H1A H 0.8635(18) 0.406(2) 0.211(2) 0.068 Uiso 1 1 d . . . H1B H 0.907(2) 0.367(2) 0.302(2) 0.068 Uiso 1 1 d . . . H1C H 0.8690(19) 0.323(2) 0.195(3) 0.068 Uiso 1 1 d . . . B2 B 0.5000 0.2992(2) 0.2500 0.0365(10) Uani 1 2 d S . . C1 C 0.79214(14) 0.34443(13) 0.23604(18) 0.0328(6) Uani 1 1 d . . . C2 C 0.71070(13) 0.30087(13) 0.26774(17) 0.0297(6) Uani 1 1 d . . . C3 C 0.67430(13) 0.26337(13) 0.30217(17) 0.0296(6) Uani 1 1 d . . . H3 H 0.6937 0.2273 0.3434 0.036 Uiso 1 1 calc R . . C4 C 0.60824(13) 0.28336(13) 0.27095(17) 0.0298(6) Uani 1 1 d . . . C5 C 0.57878(13) 0.33533(13) 0.20797(16) 0.0301(6) Uani 1 1 d . . . C6 C 0.61437(13) 0.37278(14) 0.17480(17) 0.0325(6) Uani 1 1 d . . . H6 H 0.5948 0.4086 0.1333 0.039 Uiso 1 1 calc R . . C7 C 0.68224(13) 0.35308(13) 0.20803(17) 0.0310(4) Uani 1 1 d . . . C8 C 0.82354(13) 0.24207(13) 0.33128(18) 0.0327(6) Uani 1 1 d . . . C9 C 0.82653(14) 0.18655(14) 0.28183(19) 0.0362(6) Uani 1 1 d . . . C10 C 0.86969(15) 0.13406(15) 0.3271(2) 0.0427(7) Uani 1 1 d . . . H10 H 0.8732 0.0963 0.2946 0.051 Uiso 1 1 calc R . . C11 C 0.90835(15) 0.13555(15) 0.4200(2) 0.0432(7) Uani 1 1 d . . . C12 C 0.90326(15) 0.19104(14) 0.4659(2) 0.0416(7) Uani 1 1 d . . . H12 H 0.9294 0.1920 0.5290 0.050 Uiso 1 1 calc R . . C13 C 0.86189(14) 0.24518(14) 0.42397(18) 0.0369(6) Uani 1 1 d . . . C14 C 0.78352(18) 0.18480(16) 0.1812(2) 0.0486(8) Uani 1 1 d . . . H14A H 0.7361 0.1939 0.1663 0.073 Uiso 1 1 calc R . . H14B H 0.7870 0.1401 0.1587 0.073 Uiso 1 1 calc R . . H14C H 0.7996 0.2193 0.1538 0.073 Uiso 1 1 calc R . . C15 C 0.95394(18) 0.07580(17) 0.4678(3) 0.0625(10) Uani 1 1 d . . . H15A H 0.9939 0.0764 0.4575 0.094 Uiso 1 1 calc R . . H15B H 0.9289 0.0335 0.4446 0.094 Uiso 1 1 calc R . . H15C H 0.9683 0.0790 0.5320 0.094 Uiso 1 1 calc R . . C16 C 0.85766(18) 0.30580(17) 0.4755(2) 0.0519(8) Uani 1 1 d . . . H16A H 0.8761 0.3455 0.4594 0.078 Uiso 1 1 calc R . . H16B H 0.8839 0.2971 0.5396 0.078 Uiso 1 1 calc R . . H16C H 0.8102 0.3141 0.4609 0.078 Uiso 1 1 calc R . . C17 C 0.72272(13) 0.43276(13) 0.12765(17) 0.0310(4) Uani 1 1 d . . . C18 C 0.69423(16) 0.41569(15) 0.0366(2) 0.0414(7) Uani 1 1 d . . . C19 C 0.68233(17) 0.46835(17) -0.0233(2) 0.0475(8) Uani 1 1 d . . . H19 H 0.6623 0.4584 -0.0853 0.057 Uiso 1 1 calc R . . C20 C 0.69857(17) 0.53484(16) 0.0042(2) 0.0458(8) Uani 1 1 d . . . C21 C 0.72687(16) 0.54885(15) 0.0953(2) 0.0436(7) Uani 1 1 d . . . H21 H 0.7383 0.5942 0.1149 0.052 Uiso 1 1 calc R . . C22 C 0.73887(14) 0.49856(14) 0.15798(19) 0.0378(6) Uani 1 1 d . . . C23 C 0.6779(2) 0.34499(17) 0.0064(2) 0.0616(10) Uani 1 1 d . . . H23A H 0.7199 0.3198 0.0227 0.092 Uiso 1 1 calc R . . H23B H 0.6501 0.3440 -0.0586 0.092 Uiso 1 1 calc R . . H23C H 0.6527 0.3242 0.0350 0.092 Uiso 1 1 calc R . . C24 C 0.6846(2) 0.59096(19) -0.0626(3) 0.0651(10) Uani 1 1 d . . . H24A H 0.6956 0.6345 -0.0315 0.098 Uiso 1 1 calc R . . H24B H 0.6366 0.5903 -0.1065 0.098 Uiso 1 1 calc R . . H24C H 0.7126 0.5845 -0.0931 0.098 Uiso 1 1 calc R . . C25 C 0.76770(18) 0.51375(16) 0.2559(2) 0.0522(8) Uani 1 1 d . . . H25A H 0.7738 0.5627 0.2653 0.078 Uiso 1 1 calc R . . H25B H 0.8116 0.4911 0.2882 0.078 Uiso 1 1 calc R . . H25C H 0.7366 0.4974 0.2780 0.078 Uiso 1 1 calc R . . O3 O 0.93337(19) 0.3894(2) 0.0612(2) 0.1002(11) Uani 1 1 d U A . C26 C 0.8762(3) 0.4937(3) 0.0221(5) 0.129(2) Uani 1 1 d . . . H26A H 0.8326 0.5154 -0.0151 0.194 Uiso 1 1 calc R . . H26B H 0.9105 0.5115 0.0064 0.194 Uiso 1 1 calc R . . H26C H 0.8899 0.5032 0.0851 0.194 Uiso 1 1 calc R . . C27 C 0.8702(3) 0.4234(3) 0.0078(4) 0.1146(17) Uani 1 1 d U . . H27A H 0.8555 0.4139 -0.0561 0.138 Uiso 1 1 calc R . . H27B H 0.8350 0.4056 0.0228 0.138 Uiso 1 1 calc R . . C28 C 0.9208(7) 0.3181(5) 0.0363(8) 0.133(3) Uani 0.680(6) 1 d PDU A 1 H28A H 0.8719 0.3086 0.0124 0.160 Uiso 0.680(6) 1 calc PR A 1 H28B H 0.9455 0.2898 0.0901 0.160 Uiso 0.680(6) 1 calc PR A 1 C29 C 0.9431(6) 0.2993(5) -0.0328(7) 0.126(3) Uani 0.680(6) 1 d PDU A 1 H29A H 0.9344 0.2512 -0.0472 0.189 Uiso 0.680(6) 1 calc PR A 1 H29B H 0.9917 0.3084 -0.0093 0.189 Uiso 0.680(6) 1 calc PR A 1 H29C H 0.9177 0.3262 -0.0869 0.189 Uiso 0.680(6) 1 calc PR A 1 C28' C 0.9760(13) 0.3670(8) 0.0257(16) 0.133(3) Uani 0.320(6) 1 d PD A 2 H28C H 1.0232 0.3834 0.0592 0.160 Uiso 0.320(6) 1 calc PR A 2 H28D H 0.9579 0.3762 -0.0389 0.160 Uiso 0.320(6) 1 calc PR A 2 C29' C 0.9666(13) 0.2929(10) 0.0469(16) 0.126(3) Uani 0.320(6) 1 d PD A 2 H29D H 0.9930 0.2630 0.0284 0.189 Uiso 0.320(6) 1 calc PR A 2 H29E H 0.9185 0.2807 0.0146 0.189 Uiso 0.320(6) 1 calc PR A 2 H29F H 0.9822 0.2879 0.1112 0.189 Uiso 0.320(6) 1 calc PR A 2 O4 O 1.0136(5) 0.5439(3) 0.2501(12) 0.092(3) Uani 0.50 1 d PDU . 1 C30 C 0.9193(8) 0.5729(12) 0.2755(13) 0.123(6) Uani 0.50 1 d PDU . 1 C31 C 0.9797(6) 0.5970(6) 0.2666(10) 0.113(4) Uani 0.50 1 d PDU . 1 C32 C 1.0720(7) 0.5737(11) 0.2518(11) 0.118(6) Uani 0.50 1 d PDU . 1 C33 C 1.0560(6) 0.6090(7) 0.1648(7) 0.1146(17) Uani 0.50 1 d PDU . 1 O5 O 0.9965(10) 0.2021(7) 0.2254(10) 0.137(6) Uiso 0.320(6) 1 d PD A -1 H5 H 0.9930 0.1961 0.1741 0.206 Uiso 0.320(6) 1 d PR A -1 C34 C 1.0174(9) 0.1357(8) 0.2790(10) 0.107(6) Uiso 0.320(6) 1 d PD A -1 H34A H 1.0536 0.1448 0.3392 0.160 Uiso 0.320(6) 1 calc PR A -1 H34B H 1.0337 0.1035 0.2489 0.160 Uiso 0.320(6) 1 calc PR A -1 H34C H 0.9782 0.1165 0.2829 0.160 Uiso 0.320(6) 1 calc PR A -1 O6 O 0.9724(6) 0.0022(6) 0.2648(8) 0.128(3) Uiso 0.50 1 d PD B -1 H6A H 0.9821 -0.0388 0.2771 0.192 Uiso 0.50 1 d PR B -1 C35 C 0.9936(10) 0.0134(9) 0.2035(12) 0.146(6) Uiso 0.50 1 d PD B -1 H35A H 0.9898 0.0617 0.1890 0.220 Uiso 0.50 1 calc PR B -1 H35B H 0.9656 -0.0125 0.1494 0.220 Uiso 0.50 1 calc PR B -1 H35C H 1.0410 -0.0008 0.2270 0.220 Uiso 0.50 1 calc PR B -1 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 K1 0.0340(5) 0.0659(7) 0.0567(6) 0.000 0.0229(5) 0.000 O1 0.0266(9) 0.0481(11) 0.0350(10) 0.0070(9) 0.0184(8) 0.0003(8) O2 0.0262(10) 0.0540(12) 0.0364(10) 0.0102(9) 0.0166(8) 0.0061(8) N1 0.0294(11) 0.0320(11) 0.0359(12) 0.0071(9) 0.0176(10) 0.0079(9) N2 0.0288(11) 0.0348(12) 0.0349(12) 0.0086(10) 0.0171(10) 0.0053(9) B1 0.0365(18) 0.0467(19) 0.061(2) 0.0127(18) 0.0295(18) 0.0083(15) B2 0.030(2) 0.048(3) 0.035(2) 0.000 0.0185(19) 0.000 C1 0.0328(14) 0.0321(13) 0.0378(14) 0.0045(11) 0.0199(12) 0.0040(11) C2 0.0273(13) 0.0337(13) 0.0309(13) 0.0017(11) 0.0157(11) 0.0057(10) C3 0.0298(13) 0.0318(13) 0.0284(12) 0.0044(11) 0.0143(11) 0.0034(10) C4 0.0294(13) 0.0345(13) 0.0289(13) -0.0022(11) 0.0164(11) -0.0020(11) C5 0.0245(12) 0.0391(14) 0.0279(12) 0.0004(11) 0.0128(10) 0.0037(11) C6 0.0312(14) 0.0384(14) 0.0290(13) 0.0073(11) 0.0146(11) 0.0079(11) C7 0.0289(9) 0.0353(10) 0.0335(9) 0.0064(8) 0.0183(8) 0.0042(8) C8 0.0284(13) 0.0341(14) 0.0371(14) 0.0085(11) 0.0165(12) 0.0072(11) C9 0.0340(14) 0.0363(14) 0.0417(15) 0.0042(12) 0.0201(12) 0.0051(12) C10 0.0415(16) 0.0336(15) 0.0553(18) -0.0006(13) 0.0243(15) 0.0052(13) C11 0.0331(15) 0.0341(15) 0.0522(18) 0.0092(13) 0.0108(14) 0.0085(12) C12 0.0363(15) 0.0426(16) 0.0400(16) 0.0058(13) 0.0126(13) 0.0047(13) C13 0.0320(14) 0.0397(15) 0.0357(15) 0.0048(12) 0.0128(12) 0.0046(12) C14 0.062(2) 0.0437(17) 0.0405(16) 0.0023(14) 0.0240(15) 0.0138(15) C15 0.049(2) 0.0454(18) 0.071(2) 0.0137(17) 0.0090(18) 0.0186(16) C16 0.058(2) 0.0514(19) 0.0376(16) -0.0031(14) 0.0144(15) 0.0141(16) C17 0.0289(9) 0.0353(10) 0.0335(9) 0.0064(8) 0.0183(8) 0.0042(8) C18 0.0462(17) 0.0421(16) 0.0440(16) 0.0052(13) 0.0276(14) 0.0029(13) C19 0.056(2) 0.057(2) 0.0368(16) 0.0112(14) 0.0275(15) 0.0043(15) C20 0.0513(18) 0.0448(17) 0.0513(18) 0.0174(14) 0.0320(16) 0.0093(14) C21 0.0455(17) 0.0354(15) 0.0534(18) 0.0113(14) 0.0257(15) 0.0033(13) C22 0.0329(14) 0.0400(15) 0.0443(16) 0.0049(13) 0.0209(12) 0.0066(12) C23 0.095(3) 0.052(2) 0.0446(18) -0.0044(15) 0.038(2) -0.0092(19) C24 0.077(3) 0.062(2) 0.063(2) 0.0297(18) 0.038(2) 0.0108(19) C25 0.056(2) 0.0441(17) 0.0493(18) 0.0009(15) 0.0185(16) 0.0033(15) O3 0.100(2) 0.114(3) 0.080(2) -0.0045(19) 0.0356(18) 0.0229(19) C26 0.111(5) 0.104(5) 0.125(5) -0.006(4) 0.013(4) 0.024(4) C27 0.091(3) 0.130(4) 0.094(3) 0.020(3) 0.018(3) 0.005(3) C28 0.180(10) 0.083(5) 0.155(8) -0.015(5) 0.094(7) 0.022(5) C29 0.130(7) 0.121(6) 0.131(7) -0.041(7) 0.062(6) -0.023(5) C28' 0.180(10) 0.083(5) 0.155(8) -0.015(5) 0.094(7) 0.022(5) C29' 0.130(7) 0.121(6) 0.131(7) -0.041(7) 0.062(6) -0.023(5) O4 0.082(8) 0.069(3) 0.136(4) 0.015(5) 0.058(6) 0.016(3) C30 0.114(8) 0.135(9) 0.147(10) -0.040(7) 0.082(8) -0.045(6) C31 0.094(7) 0.095(7) 0.163(9) -0.022(6) 0.071(6) 0.011(5) C32 0.110(9) 0.106(8) 0.148(10) 0.027(7) 0.067(7) -0.010(7) C33 0.091(3) 0.130(4) 0.094(3) 0.020(3) 0.018(3) 0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag K1 H1B 2.68(4) . ? K1 O4 2.794(7) . ? K1 O4 2.794(7) 2_755 ? K1 H1A 2.79(4) . ? K1 O3 2.841(3) 2_755 ? K1 O3 2.841(3) . ? K1 H1C 3.06(4) . ? K1 B1 3.092(4) . ? K1 B1 3.092(4) 2_755 ? K1 H1A 2.79(4) . ? K1 H1B 2.68(4) . ? K1 H1C 3.06(4) . ? O1 C4 1.369(3) . ? O1 B2 1.471(3) . ? O2 C5 1.357(3) . ? O2 B2 1.488(3) . ? N1 C1 1.361(3) . ? N1 C2 1.408(3) . ? N1 C8 1.440(3) . ? N2 C1 1.360(3) . ? N2 C7 1.406(3) . ? N2 C17 1.431(3) . ? B1 H1C 1.03(4) . ? B1 H1A 1.03(4) . ? B1 H1B 1.13(4) . ? B1 C1 1.582(4) . ? B1 H1A 1.03(4) . ? B1 H1B 1.13(4) . ? B1 H1C 1.03(4) . ? B2 O1 1.471(3) 2_655 ? B2 O2 1.488(3) 2_655 ? C2 C7 1.377(4) . ? C2 C3 1.405(4) . ? C3 C4 1.370(4) . ? C3 H3 0.9500 . ? C4 C5 1.405(4) . ? C5 C6 1.376(4) . ? C6 C7 1.401(4) . ? C6 H6 0.9500 . ? C8 C13 1.396(4) . ? C8 C9 1.399(4) . ? C9 C10 1.382(4) . ? C9 C14 1.517(4) . ? C10 C11 1.398(4) . ? C10 H10 0.9500 . ? C11 C12 1.377(4) . ? C11 C15 1.524(4) . ? C12 C13 1.377(4) . ? C12 H12 0.9500 . ? C13 C16 1.509(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.384(4) . ? C17 C18 1.407(4) . ? C18 C19 1.389(4) . ? C18 C23 1.476(4) . ? C19 C20 1.386(5) . ? C19 H19 0.9500 . ? C20 C21 1.395(5) . ? C20 C24 1.508(4) . ? C21 C22 1.385(4) . ? C21 H21 0.9500 . ? C22 C25 1.501(4) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? O3 C28' 1.40(2) . ? O3 C27 1.441(6) . ? O3 C28 1.460(10) . ? C26 C27 1.407(8) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.507(11) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C28' C29' 1.547(17) . ? C28' H28C 0.9900 . ? C28' H28D 0.9900 . ? C29' H29D 0.9800 . ? C29' H29E 0.9800 . ? C29' H29F 0.9800 . ? O4 O4 0.602(15) 2_755 ? O4 C31 1.116(11) 2_755 ? O4 C31 1.394(8) . ? O4 C32 1.413(9) . ? O4 C30 1.83(2) 2_755 ? C30 C32 0.58(2) 2_755 ? C30 C33 1.15(2) 2_755 ? C30 C31 1.496(9) . ? C30 O4 1.83(2) 2_755 ? C31 O4 1.116(11) 2_755 ? C31 C32 1.14(2) 2_755 ? C31 C31 1.26(2) 2_755 ? C31 C33 1.693(16) 2_755 ? C32 C30 0.58(2) 2_755 ? C32 C31 1.14(2) 2_755 ? C32 C33 1.514(9) . ? C33 C30 1.15(2) 2_755 ? C33 C31 1.693(16) 2_755 ? O5 C34 1.540(14) . ? O5 H5 0.8400 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? O6 C35 1.337(12) . ? O6 H6A 0.8400 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 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 H1B K1 O4 111.4(9) . . ? H1B K1 O4 99.6(8) . 2_755 ? O4 K1 O4 12.4(3) . 2_755 ? H1B K1 H1A 33.6(10) . . ? O4 K1 H1A 95.1(8) . . ? O4 K1 H1A 83.0(8) 2_755 . ? H1B K1 O3 71.8(8) . 2_755 ? O4 K1 O3 95.6(4) . 2_755 ? O4 K1 O3 95.7(4) 2_755 2_755 ? H1A K1 O3 102.4(8) . 2_755 ? H1B K1 O3 105.0(8) . . ? O4 K1 O3 95.7(4) . . ? O4 K1 O3 95.6(4) 2_755 . ? H1A K1 O3 77.8(8) . . ? O3 K1 O3 168.70(16) 2_755 . ? H1B K1 H1C 36.3(11) . . ? O4 K1 H1C 127.0(8) . . ? O4 K1 H1C 115.3(8) 2_755 . ? H1A K1 H1C 32.6(10) . . ? O3 K1 H1C 102.8(7) 2_755 . ? O3 K1 H1C 71.2(7) . . ? H1B K1 B1 21.0(8) . . ? O4 K1 B1 112.96(17) . . ? O4 K1 B1 100.63(17) 2_755 . ? H1A K1 B1 19.3(8) . . ? O3 K1 B1 92.71(11) 2_755 . ? O3 K1 B1 84.02(11) . . ? H1C K1 B1 19.2(8) . . ? H1B K1 B1 141.2(8) . 2_755 ? O4 K1 B1 100.63(17) . 2_755 ? O4 K1 B1 112.96(17) 2_755 2_755 ? H1A K1 B1 162.4(8) . 2_755 ? O3 K1 B1 84.02(11) 2_755 2_755 ? O3 K1 B1 92.71(11) . 2_755 ? H1C K1 B1 130.2(8) . 2_755 ? B1 K1 B1 146.42(15) . 2_755 ? H1B K1 H1A 33.6(10) . . ? O4 K1 H1A 95.1(8) . . ? O4 K1 H1A 83.0(8) 2_755 . ? H1A K1 H1A 0(2) . . ? O3 K1 H1A 102.4(8) 2_755 . ? O3 K1 H1A 77.8(8) . . ? H1C K1 H1A 32.6(10) . . ? B1 K1 H1A 19.3(8) . . ? B1 K1 H1A 162.4(8) 2_755 . ? H1B K1 H1B 0.0(18) . . ? O4 K1 H1B 111.4(8) . . ? O4 K1 H1B 99.6(8) 2_755 . ? H1A K1 H1B 33.6(10) . . ? O3 K1 H1B 71.8(8) 2_755 . ? O3 K1 H1B 105.0(8) . . ? H1C K1 H1B 36.3(11) . . ? B1 K1 H1B 21.0(8) . . ? B1 K1 H1B 141.2(8) 2_755 . ? H1A K1 H1B 33.6(10) . . ? H1B K1 H1C 36.3(11) . . ? O4 K1 H1C 127.0(8) . . ? O4 K1 H1C 115.3(8) 2_755 . ? H1A K1 H1C 32.6(10) . . ? O3 K1 H1C 102.8(7) 2_755 . ? O3 K1 H1C 71.2(7) . . ? H1C K1 H1C 0.0(16) . . ? B1 K1 H1C 19.2(8) . . ? B1 K1 H1C 130.2(8) 2_755 . ? H1A K1 H1C 32.6(10) . . ? H1B K1 H1C 36.3(11) . . ? C4 O1 B2 107.15(19) . . ? C5 O2 B2 106.71(17) . . ? C1 N1 C2 110.7(2) . . ? C1 N1 C8 124.4(2) . . ? C2 N1 C8 124.0(2) . . ? C1 N2 C7 110.4(2) . . ? C1 N2 C17 126.0(2) . . ? C7 N2 C17 123.6(2) . . ? H1C B1 H1A 108(3) . . ? H1C B1 H1B 115(3) . . ? H1A B1 H1B 95(3) . . ? H1C B1 C1 109(2) . . ? H1A B1 C1 112(2) . . ? H1B B1 C1 116.8(19) . . ? H1C B1 K1 79(2) . . ? H1A B1 K1 64(2) . . ? H1B B1 K1 58.6(19) . . ? C1 B1 K1 172.0(3) . . ? H1C B1 H1A 108(3) . . ? H1A B1 H1A 0(5) . . ? H1B B1 H1A 95(3) . . ? C1 B1 H1A 112(2) . . ? K1 B1 H1A 64(2) . . ? H1C B1 H1B 115(3) . . ? H1A B1 H1B 95(3) . . ? H1B B1 H1B 0(6) . . ? C1 B1 H1B 116.8(19) . . ? K1 B1 H1B 58.6(19) . . ? H1A B1 H1B 95(3) . . ? H1C B1 H1C 0(6) . . ? H1A B1 H1C 108(3) . . ? H1B B1 H1C 115(3) . . ? C1 B1 H1C 109(2) . . ? K1 B1 H1C 79(2) . . ? H1A B1 H1C 108(3) . . ? H1B B1 H1C 115(3) . . ? O1 B2 O1 112.8(3) 2_655 . ? O1 B2 O2 104.84(10) 2_655 2_655 ? O1 B2 O2 112.85(10) . 2_655 ? O1 B2 O2 112.85(10) 2_655 . ? O1 B2 O2 104.84(10) . . ? O2 B2 O2 108.8(3) 2_655 . ? N2 C1 N1 106.0(2) . . ? N2 C1 B1 126.5(2) . . ? N1 C1 B1 127.4(2) . . ? C7 C2 C3 122.7(2) . . ? C7 C2 N1 106.0(2) . . ? C3 C2 N1 131.3(2) . . ? C4 C3 C2 114.0(2) . . ? C4 C3 H3 123.0 . . ? C2 C3 H3 123.0 . . ? O1 C4 C3 127.0(2) . . ? O1 C4 C5 109.9(2) . . ? C3 C4 C5 123.1(2) . . ? O2 C5 C6 126.4(2) . . ? O2 C5 C4 110.5(2) . . ? C6 C5 C4 123.1(2) . . ? C5 C6 C7 113.7(2) . . ? C5 C6 H6 123.2 . . ? C7 C6 H6 123.2 . . ? C2 C7 C6 123.3(2) . . ? C2 C7 N2 106.8(2) . . ? C6 C7 N2 129.8(2) . . ? C13 C8 C9 122.0(2) . . ? C13 C8 N1 120.0(2) . . ? C9 C8 N1 117.9(2) . . ? C10 C9 C8 118.1(3) . . ? C10 C9 C14 121.5(3) . . ? C8 C9 C14 120.4(2) . . ? C9 C10 C11 121.1(3) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 118.6(3) . . ? C12 C11 C15 121.8(3) . . ? C10 C11 C15 119.6(3) . . ? C13 C12 C11 122.7(3) . . ? C13 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? C12 C13 C8 117.4(3) . . ? C12 C13 C16 121.8(3) . . ? C8 C13 C16 120.8(2) . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 122.6(2) . . ? C22 C17 N2 119.5(2) . . ? C18 C17 N2 117.8(2) . . ? C19 C18 C17 117.0(3) . . ? C19 C18 C23 121.7(3) . . ? C17 C18 C23 121.4(3) . . ? C20 C19 C18 122.4(3) . . ? C20 C19 H19 118.8 . . ? C18 C19 H19 118.8 . . ? C19 C20 C21 118.2(3) . . ? C19 C20 C24 121.1(3) . . ? C21 C20 C24 120.7(3) . . ? C22 C21 C20 122.0(3) . . ? C22 C21 H21 119.0 . . ? C20 C21 H21 119.0 . . ? C17 C22 C21 117.8(3) . . ? C17 C22 C25 120.1(3) . . ? C21 C22 C25 122.0(3) . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C28' O3 C27 122.3(11) . . ? C28' O3 C28 69.5(10) . . ? C27 O3 C28 105.6(7) . . ? C28' O3 K1 113.7(11) . . ? C27 O3 K1 120.8(3) . . ? C28 O3 K1 110.5(5) . . ? C27 C26 H26A 109.5 . . ? C27 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C27 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C26 C27 O3 111.4(5) . . ? C26 C27 H27A 109.3 . . ? O3 C27 H27A 109.3 . . ? C26 C27 H27B 109.3 . . ? O3 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? O3 C28 C29 112.0(8) . . ? O3 C28 H28A 109.2 . . ? C29 C28 H28A 109.2 . . ? O3 C28 H28B 109.2 . . ? C29 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O3 C28' C29' 90.6(16) . . ? O3 C28' H28C 113.5 . . ? C29' C28' H28C 113.5 . . ? O3 C28' H28D 113.5 . . ? C29' C28' H28D 113.5 . . ? H28C C28' H28D 110.8 . . ? C28' C29' H29D 109.5 . . ? C28' C29' H29E 109.5 . . ? H29D C29' H29E 109.5 . . ? C28' C29' H29F 109.5 . . ? H29D C29' H29F 109.5 . . ? H29E C29' H29F 109.5 . . ? O4 O4 C31 104.4(10) 2_755 2_755 ? O4 O4 C31 50.9(9) 2_755 . ? C31 O4 C31 59.1(11) 2_755 . ? O4 O4 C32 155.3(10) 2_755 . ? C31 O4 C32 52.0(10) 2_755 . ? C31 O4 C32 104.8(12) . . ? O4 O4 C30 158(2) 2_755 2_755 ? C31 O4 C30 54.9(8) 2_755 2_755 ? C31 O4 C30 112.7(10) . 2_755 ? C32 O4 C30 14.4(13) . 2_755 ? O4 O4 K1 83.82(15) 2_755 . ? C31 O4 K1 164.4(13) 2_755 . ? C31 O4 K1 133.0(7) . . ? C32 O4 K1 120.8(10) . . ? C30 O4 K1 114.3(7) 2_755 . ? C32 C30 C33 119(3) 2_755 2_755 ? C32 C30 C31 43(2) 2_755 . ? C33 C30 C31 78.4(11) 2_755 . ? C32 C30 O4 38(3) 2_755 2_755 ? C33 C30 O4 106.8(12) 2_755 2_755 ? C31 C30 O4 37.6(6) . 2_755 ? O4 C31 C32 77.5(11) 2_755 2_755 ? O4 C31 C31 71.5(8) 2_755 2_755 ? C32 C31 C31 135.6(18) 2_755 2_755 ? O4 C31 O4 24.7(7) 2_755 . ? C32 C31 O4 102.0(12) 2_755 . ? C31 C31 O4 49.4(6) 2_755 . ? O4 C31 C30 87.4(13) 2_755 . ? C32 C31 C30 20.0(10) 2_755 . ? C31 C31 C30 154.4(16) 2_755 . ? O4 C31 C30 111.8(13) . . ? O4 C31 C33 117.6(12) 2_755 2_755 ? C32 C31 C33 60.9(7) 2_755 2_755 ? C31 C31 C33 163.4(17) 2_755 2_755 ? O4 C31 C33 135.1(12) . 2_755 ? C30 C31 C33 41.6(8) . 2_755 ? C30 C32 C31 117(3) 2_755 2_755 ? C30 C32 O4 128(4) 2_755 . ? C31 C32 O4 50.5(7) 2_755 . ? C30 C32 C33 42(2) 2_755 . ? C31 C32 C33 77.9(12) 2_755 . ? O4 C32 C33 111.6(12) . . ? C30 C33 C32 19.5(11) 2_755 . ? C30 C33 C31 59.9(8) 2_755 2_755 ? C32 C33 C31 41.2(8) . 2_755 ? C34 O5 H5 110.2 . . ? O5 C34 H34A 109.5 . . ? O5 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O5 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C35 O6 H6A 102.1 . . ? O6 C35 H35A 109.5 . . ? O6 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O6 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.987 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 950340'