# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_mrb110xi _audit_creation_date 2011-12-08T11:38:57-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C28 H38 O8' _chemical_formula_moiety 'C28 H38 O8' _chemical_formula_weight 502.58 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5690(2) _cell_length_b 8.0724(2) _cell_length_c 17.2904(3) _cell_angle_alpha 90 _cell_angle_beta 96.872(2) _cell_angle_gamma 90 _cell_volume 1326.00(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10193 _cell_measurement_theta_min 3.9125 _cell_measurement_theta_max 34.78 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.92684 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 -0.0566373922 _diffrn_orient_matrix_ub_12 0.0544698751 _diffrn_orient_matrix_ub_13 0.0043685209 _diffrn_orient_matrix_ub_21 -0.0486018183 _diffrn_orient_matrix_ub_22 -0.062699514 _diffrn_orient_matrix_ub_23 -0.0139217685 _diffrn_orient_matrix_ub_31 -0.0014772605 _diffrn_orient_matrix_ub_32 -0.0286515633 _diffrn_orient_matrix_ub_33 0.0386505289 _diffrn_measurement_device_type 'Oxford Diffraction Gemini diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_unetI/netI 0.0402 _diffrn_reflns_number 30818 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 34.85 _diffrn_reflns_theta_full 33 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.961 _reflns_number_total 5538 _reflns_number_gt 3609 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0964P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5538 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.051 _refine_ls_wR_factor_ref 0.1514 _refine_ls_wR_factor_gt 0.1371 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.553 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.069 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C10 C 0.47787(9) 0.42536(12) 0.47260(5) 0.01592(18) Uani 1 1 d . . . H10 H 0.3876 0.4571 0.4408 0.019 Uiso 1 1 calc R . . C11 C 0.44644(10) 0.27083(12) 0.52031(6) 0.01745(18) Uani 1 1 d . . . H11A H 0.4891 0.1729 0.4979 0.021 Uiso 1 1 calc R . . H11B H 0.4923 0.2847 0.5744 0.021 Uiso 1 1 calc R . . C12 C 0.29138(10) 0.23758(13) 0.52263(6) 0.0209(2) Uani 1 1 d . . . O12 O 0.20236(8) 0.27096(11) 0.46889(5) 0.0291(2) Uani 1 1 d . . . C13 C 0.25464(14) 0.1566(2) 0.59590(8) 0.0456(4) Uani 1 1 d . . . H13A H 0.1576 0.1158 0.5874 0.068 Uiso 1 1 calc R . . H13B H 0.2637 0.2376 0.6384 0.068 Uiso 1 1 calc R . . H13C H 0.3187 0.0637 0.6096 0.068 Uiso 1 1 calc R . . C1 C 0.58415(9) 0.39288(12) 0.41592(5) 0.01592(18) Uani 1 1 d . . . C2 C 0.72103(10) 0.33994(12) 0.44350(5) 0.01769(18) Uani 1 1 d . . . O2 O 0.74629(8) 0.31527(10) 0.52240(4) 0.02268(17) Uani 1 1 d . . . C21 C 0.88493(11) 0.27211(18) 0.55503(6) 0.0315(3) Uani 1 1 d . . . H21A H 0.9127 0.1682 0.5318 0.047 Uiso 1 1 calc R . . H21B H 0.8874 0.2581 0.6115 0.047 Uiso 1 1 calc R . . H21C H 0.9503 0.3603 0.5443 0.047 Uiso 1 1 calc R . . C3 C 0.82301(10) 0.31128(13) 0.39353(6) 0.0201(2) Uani 1 1 d . . . H3 H 0.9162 0.2809 0.4136 0.024 Uiso 1 1 calc R . . C4 C 0.78497(10) 0.32824(12) 0.31354(5) 0.01803(18) Uani 1 1 d . . . O4 O 0.87438(8) 0.29812(11) 0.25887(4) 0.02555(18) Uani 1 1 d . . . C41 C 1.00998(13) 0.2343(2) 0.28640(7) 0.0449(4) Uani 1 1 d . . . H41A H 1.064 0.3186 0.318 0.067 Uiso 1 1 calc R . . H41B H 1.0596 0.2047 0.2419 0.067 Uiso 1 1 calc R . . H41C H 0.9997 0.1356 0.3182 0.067 Uiso 1 1 calc R . . C5 C 0.64808(10) 0.37630(11) 0.28449(5) 0.01541(17) Uani 1 1 d . . . O5 O 0.60972(7) 0.37628(9) 0.20460(4) 0.01757(15) Uani 1 1 d . . . C51 C 0.65470(12) 0.51714(13) 0.16513(6) 0.0255(2) Uani 1 1 d . . . H51A H 0.5989 0.6137 0.1769 0.038 Uiso 1 1 calc R . . H51B H 0.6418 0.4967 0.1089 0.038 Uiso 1 1 calc R . . H51C H 0.7544 0.5382 0.1824 0.038 Uiso 1 1 calc R . . C6 C 0.54851(9) 0.41171(11) 0.33505(5) 0.01515(17) Uani 1 1 d . . . C61 C 0.40307(10) 0.46741(13) 0.30087(5) 0.01856(19) Uani 1 1 d . . . H61A H 0.3975 0.4691 0.2439 0.028 Uiso 1 1 calc R . . H61B H 0.3849 0.5788 0.3198 0.028 Uiso 1 1 calc R . . H61C H 0.3326 0.3904 0.3167 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C10 0.0144(4) 0.0192(4) 0.0140(4) 0.0001(3) 0.0011(3) 0.0024(3) C11 0.0152(4) 0.0206(4) 0.0162(4) 0.0005(3) 0.0005(3) 0.0017(3) C12 0.0175(4) 0.0253(5) 0.0199(4) 0.0025(4) 0.0021(3) 0.0007(4) O12 0.0186(4) 0.0437(5) 0.0236(4) 0.0064(3) -0.0028(3) -0.0028(3) C13 0.0222(6) 0.0760(11) 0.0386(7) 0.0328(7) 0.0036(5) -0.0005(6) C1 0.0147(4) 0.0187(4) 0.0141(4) -0.0001(3) 0.0003(3) 0.0018(3) C2 0.0167(4) 0.0240(5) 0.0121(4) 0.0005(3) 0.0007(3) 0.0036(3) O2 0.0172(3) 0.0379(4) 0.0126(3) 0.0029(3) 0.0002(2) 0.0093(3) C21 0.0193(5) 0.0568(8) 0.0170(5) 0.0059(5) -0.0031(4) 0.0112(5) C3 0.0156(4) 0.0295(5) 0.0150(4) 0.0009(4) 0.0009(3) 0.0059(3) C4 0.0170(4) 0.0235(5) 0.0138(4) 0.0000(3) 0.0028(3) 0.0032(3) O4 0.0192(3) 0.0428(5) 0.0152(3) 0.0015(3) 0.0047(3) 0.0093(3) C41 0.0239(6) 0.0890(12) 0.0231(5) 0.0061(6) 0.0076(4) 0.0237(7) C5 0.0174(4) 0.0160(4) 0.0122(4) -0.0001(3) -0.0007(3) -0.0001(3) O5 0.0224(3) 0.0185(3) 0.0113(3) 0.0000(2) -0.0001(2) -0.0023(3) C51 0.0322(6) 0.0223(5) 0.0204(5) 0.0064(4) -0.0036(4) -0.0060(4) C6 0.0157(4) 0.0152(4) 0.0139(4) -0.0008(3) -0.0008(3) 0.0009(3) C61 0.0166(4) 0.0216(5) 0.0164(4) -0.0006(3) -0.0027(3) 0.0024(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C10 C1 1.5172(13) . ? C10 C11 1.5448(14) . ? C10 C10 1.5599(19) 3_666 ? C10 H10 1 . ? C11 C12 1.5130(14) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 O12 1.2133(12) . ? C12 C13 1.5042(16) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C1 C2 1.4058(13) . ? C1 C6 1.4072(12) . ? C2 O2 1.3713(11) . ? C2 C3 1.3979(14) . ? O2 C21 1.4214(12) . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C3 C4 1.3942(13) . ? C3 H3 0.95 . ? C4 O4 1.3705(12) . ? C4 C5 1.4005(13) . ? O4 C41 1.4241(14) . ? C41 H41A 0.98 . ? C41 H41B 0.98 . ? C41 H41C 0.98 . ? C5 O5 1.3862(11) . ? C5 C6 1.3976(13) . ? O5 C51 1.4192(12) . ? C51 H51A 0.98 . ? C51 H51B 0.98 . ? C51 H51C 0.98 . ? C6 C61 1.5138(12) . ? C61 H61A 0.98 . ? C61 H61B 0.98 . ? C61 H61C 0.98 . ? 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 C1 C10 C11 113.19(8) . . ? C1 C10 C10 111.82(9) . 3_666 ? C11 C10 C10 110.83(9) . 3_666 ? C1 C10 H10 106.9 . . ? C11 C10 H10 106.9 . . ? C10 C10 H10 106.9 3_666 . ? C12 C11 C10 114.30(8) . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C10 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? O12 C12 C13 121.88(10) . . ? O12 C12 C11 122.76(10) . . ? C13 C12 C11 115.35(9) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C2 C1 C6 118.36(8) . . ? C2 C1 C10 120.18(8) . . ? C6 C1 C10 121.45(8) . . ? O2 C2 C3 122.53(8) . . ? O2 C2 C1 115.33(8) . . ? C3 C2 C1 122.12(8) . . ? C2 O2 C21 118.39(8) . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C4 C3 C2 118.56(9) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? O4 C4 C3 123.81(8) . . ? O4 C4 C5 115.85(8) . . ? C3 C4 C5 120.34(9) . . ? C4 O4 C41 116.91(8) . . ? O4 C41 H41A 109.5 . . ? O4 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? O4 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O5 C5 C6 120.29(8) . . ? O5 C5 C4 118.83(8) . . ? C6 C5 C4 120.70(8) . . ? C5 O5 C51 114.81(7) . . ? O5 C51 H51A 109.5 . . ? O5 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? O5 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C5 C6 C1 119.82(8) . . ? C5 C6 C61 118.70(8) . . ? C1 C6 C61 121.48(8) . . ? C6 C61 H61A 109.5 . . ? C6 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C6 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? #===END _database_code_depnum_ccdc_archive 'CCDC 970520' ####################################################################### # # 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_mrb26ii2 _audit_creation_date 2012-03-22T15:52:20-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H32 O9' _chemical_formula_moiety 'C29 H32 O9' _chemical_formula_weight 524.55 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'p 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.3517(19) _cell_length_b 18.103(5) _cell_length_c 10.012(3) _cell_angle_alpha 90 _cell_angle_beta 96.47(2) _cell_angle_gamma 90 _cell_volume 1323.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1615 _cell_measurement_theta_min 2.7832 _cell_measurement_theta_max 27.8403 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.92742 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0009 _diffrn_orient_matrix_ub_11 0.0144596 _diffrn_orient_matrix_ub_12 0.0354658 _diffrn_orient_matrix_ub_13 0.02939 _diffrn_orient_matrix_ub_21 0.0015509 _diffrn_orient_matrix_ub_22 -0.0159019 _diffrn_orient_matrix_ub_23 0.0648002 _diffrn_orient_matrix_ub_31 0.096095 _diffrn_orient_matrix_ub_32 -0.0049963 _diffrn_orient_matrix_ub_33 0.0024724 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.082 _diffrn_reflns_av_unetI/netI 0.0884 _diffrn_reflns_number 7957 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 2406 _reflns_number_gt 2006 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2406 _refine_ls_number_parameters 357 _refine_ls_number_restraints 235 _refine_ls_R_factor_all 0.1602 _refine_ls_R_factor_gt 0.1458 _refine_ls_wR_factor_ref 0.3683 _refine_ls_wR_factor_gt 0.3562 _refine_ls_goodness_of_fit_ref 1.412 _refine_ls_restrained_S_all 1.37 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.004 _refine_diff_density_max 1.305 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.177 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4767(13) 0.5582(6) 0.3901(10) 0.033(2) Uani 1 1 d U . . C2 C 0.3917(16) 0.5290(7) 0.4949(13) 0.017(3) Uani 1 1 d U . . O2 O 0.2368(13) 0.5306(7) 0.5020(11) 0.030(2) Uani 1 1 d U . . O3 O 0.5161(12) 0.5005(5) 0.5885(10) 0.028(2) Uani 1 1 d U . . C4 C 0.7012(16) 0.5261(7) 0.5635(13) 0.019(3) Uani 1 1 d U . . C40 C 0.8355(19) 0.4687(9) 0.6166(15) 0.030(3) Uani 1 1 d U . . H40A H 0.8247 0.4603 0.7121 0.045 Uiso 1 1 calc R . . H40B H 0.9597 0.4855 0.6059 0.045 Uiso 1 1 calc R . . H40C H 0.8103 0.4225 0.5667 0.045 Uiso 1 1 calc R . . C41 C 0.7382(17) 0.5952(8) 0.6387(14) 0.025(3) Uani 1 1 d U . . C42 C 0.7654(17) 0.6530(8) 0.6921(13) 0.020(3) Uani 1 1 d U . . C43 C 0.7920(18) 0.7261(8) 0.7540(14) 0.025(3) Uani 1 1 d U . . C44 C 0.8652(19) 0.7330(8) 0.8954(15) 0.027(3) Uani 1 1 d U . . C441 C 0.897(2) 0.6653(9) 0.9801(16) 0.033(4) Uani 1 1 d U . . H44A H 0.9864 0.6336 0.9429 0.05 Uiso 1 1 calc R . . H44B H 0.7809 0.6384 0.9808 0.05 Uiso 1 1 calc R . . H44C H 0.9428 0.6796 1.0721 0.05 Uiso 1 1 calc R . . C45 C 0.9054(16) 0.8031(7) 0.9425(12) 0.017(3) Uani 1 1 d U . . O45 O 0.9893(12) 0.8108(5) 1.0729(10) 0.028(2) Uani 1 1 d U . . C451 C 0.8719(16) 0.8374(8) 1.1668(12) 0.021(3) Uani 1 1 d U . . H45A H 0.8368 0.8886 1.1447 0.032 Uiso 1 1 calc R . . H45B H 0.9364 0.8353 1.2578 0.032 Uiso 1 1 calc R . . H45C H 0.7618 0.8065 1.1621 0.032 Uiso 1 1 calc R . . C46 C 0.8723(15) 0.8664(7) 0.8627(12) 0.016(3) Uani 1 1 d U . . O46 O 0.9140(12) 0.9319(5) 0.9212(10) 0.025(2) Uani 1 1 d U . . C461 C 0.8807(17) 0.9962(7) 0.8439(13) 0.023(3) Uani 1 1 d U . . H46A H 0.9527 0.9948 0.7673 0.034 Uiso 1 1 calc R . . H46B H 0.916 1.0396 0.8995 0.034 Uiso 1 1 calc R . . H46C H 0.7502 0.9992 0.8111 0.034 Uiso 1 1 calc R . . C47 C 0.8005(15) 0.8588(7) 0.7278(13) 0.015(3) Uani 1 1 d U . . H47 H 0.7787 0.9016 0.6734 0.018 Uiso 1 1 calc R . . C48 C 0.7609(16) 0.7895(7) 0.6726(13) 0.019(3) Uani 1 1 d U . . O48 O 0.7000(12) 0.7754(6) 0.5462(9) 0.028(2) Uani 1 1 d U . . C481 C 0.641(2) 0.8369(9) 0.4653(15) 0.031(3) Uani 1 1 d U . . H48A H 0.5275 0.8565 0.4936 0.047 Uiso 1 1 calc R . . H48B H 0.6204 0.8216 0.3709 0.047 Uiso 1 1 calc R . . H48C H 0.7359 0.8753 0.4754 0.047 Uiso 1 1 calc R . . C5 C 0.6785(17) 0.5365(7) 0.4115(12) 0.020(3) Uani 1 1 d U . . C50 C 0.7746(18) 0.5963(8) 0.3554(14) 0.025(3) Uani 1 1 d U . . H50A H 0.9068 0.5877 0.3722 0.038 Uiso 1 1 calc R . . H50B H 0.7441 0.6429 0.3975 0.038 Uiso 1 1 calc R . . H50C H 0.7382 0.599 0.2583 0.038 Uiso 1 1 calc R . . C51 C 0.6971(17) 0.4660(8) 0.3450(14) 0.023(3) Uani 1 1 d U . . C52 C 0.6919(16) 0.4045(7) 0.2883(13) 0.016(3) Uani 1 1 d U . . C53 C 0.6853(15) 0.3362(7) 0.2285(12) 0.014(2) Uani 1 1 d U . . C54 C 0.6256(18) 0.3271(8) 0.0969(15) 0.028(3) Uani 1 1 d U . . C541 C 0.5840(17) 0.3915(8) 0.0061(14) 0.022(3) Uani 1 1 d U . . H54A H 0.4522 0.4015 -0.0028 0.033 Uiso 1 1 calc R . . H54B H 0.6218 0.3805 -0.0825 0.033 Uiso 1 1 calc R . . H54C H 0.6507 0.435 0.0439 0.033 Uiso 1 1 calc R . . C55 C 0.6025(18) 0.2532(8) 0.0411(14) 0.027(3) Uani 1 1 d U . . O55 O 0.5210(12) 0.2455(6) -0.0890(10) 0.029(2) Uani 1 1 d U . . C551 C 0.6350(18) 0.2178(9) -0.1846(14) 0.028(3) Uani 1 1 d U . . H55A H 0.7464 0.2477 -0.1813 0.043 Uiso 1 1 calc R . . H55B H 0.5686 0.2202 -0.275 0.043 Uiso 1 1 calc R . . H55C H 0.6679 0.1664 -0.1628 0.043 Uiso 1 1 calc R . . C56 C 0.6503(19) 0.1964(9) 0.1230(15) 0.031(3) Uani 1 1 d U . . O56 O 0.6219(12) 0.1274(5) 0.0598(9) 0.024(2) Uani 1 1 d U . . C561 C 0.667(2) 0.0642(10) 0.1383(18) 0.042(4) Uani 1 1 d U . . H56A H 0.8004 0.0589 0.1531 0.063 Uiso 1 1 calc R . . H56B H 0.6135 0.0205 0.0914 0.063 Uiso 1 1 calc R . . H56C H 0.6185 0.0693 0.2251 0.063 Uiso 1 1 calc R . . C57 C 0.7157(18) 0.2025(9) 0.2518(15) 0.030(3) Uani 1 1 d U . . H57 H 0.7506 0.1602 0.3048 0.036 Uiso 1 1 calc R . . C58 C 0.7312(16) 0.2745(8) 0.3069(13) 0.022(3) Uani 1 1 d U . . O58 O 0.7982(11) 0.2855(5) 0.4416(9) 0.020(2) Uani 1 1 d U . . C581 C 0.852(2) 0.2237(9) 0.5188(16) 0.031(3) Uani 1 1 d U . . H58A H 0.7428 0.1981 0.5437 0.047 Uiso 1 1 calc R . . H58B H 0.9285 0.2391 0.6003 0.047 Uiso 1 1 calc R . . H58C H 0.921 0.1902 0.4666 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.036(4) 0.026(4) 0.037(4) -0.001(4) 0.003(3) 0.007(3) C2 0.016(4) 0.011(4) 0.024(4) 0.000(4) -0.002(4) -0.003(3) O2 0.029(4) 0.027(4) 0.036(4) -0.005(3) 0.008(3) 0.003(3) O3 0.029(4) 0.022(4) 0.033(4) -0.003(3) 0.005(3) -0.008(3) C4 0.018(4) 0.015(4) 0.024(4) -0.002(4) 0.000(4) 0.002(4) C40 0.030(5) 0.030(5) 0.031(5) -0.003(4) 0.004(4) -0.001(4) C41 0.024(4) 0.025(5) 0.026(5) -0.002(4) 0.006(4) -0.001(4) C42 0.023(4) 0.017(5) 0.021(5) -0.004(4) 0.003(4) 0.001(4) C43 0.028(5) 0.022(5) 0.025(5) 0.001(4) 0.001(4) 0.002(4) C44 0.030(5) 0.022(5) 0.029(5) 0.001(4) 0.006(4) 0.006(4) C441 0.035(5) 0.033(5) 0.033(5) -0.003(4) 0.007(4) 0.000(4) C45 0.020(4) 0.019(5) 0.013(4) -0.008(4) 0.003(3) 0.002(4) O45 0.027(4) 0.024(4) 0.031(4) -0.004(3) -0.001(3) 0.010(3) C451 0.026(5) 0.019(5) 0.018(4) -0.009(4) 0.000(4) 0.002(4) C46 0.016(3) 0.014(3) 0.018(3) -0.001(2) 0.002(2) -0.003(2) O46 0.030(4) 0.019(4) 0.026(4) -0.001(3) -0.003(3) -0.003(3) C461 0.026(4) 0.015(5) 0.025(5) -0.006(4) -0.002(4) -0.004(4) C47 0.017(4) 0.010(4) 0.018(4) 0.000(4) -0.001(3) 0.003(3) C48 0.022(4) 0.015(5) 0.020(5) -0.005(4) 0.003(3) 0.002(4) O48 0.033(4) 0.022(4) 0.028(4) 0.000(4) 0.004(3) -0.002(3) C481 0.032(5) 0.030(5) 0.031(5) 0.002(4) 0.000(4) -0.002(4) C5 0.024(4) 0.013(4) 0.022(5) -0.003(4) 0.002(4) 0.008(4) C50 0.024(4) 0.022(5) 0.031(5) -0.002(4) 0.006(4) 0.000(4) C51 0.022(4) 0.024(5) 0.023(5) 0.002(4) 0.006(4) -0.002(4) C52 0.014(4) 0.015(5) 0.019(4) -0.004(4) 0.000(3) 0.002(3) C53 0.011(4) 0.008(4) 0.022(4) -0.004(4) 0.004(3) 0.004(3) C54 0.027(5) 0.027(5) 0.030(5) 0.000(4) 0.009(4) 0.001(4) C541 0.020(4) 0.019(5) 0.028(5) 0.000(4) 0.004(4) 0.002(4) C55 0.029(5) 0.025(5) 0.026(5) 0.001(4) 0.002(4) 0.002(4) O55 0.028(4) 0.025(4) 0.032(4) -0.002(4) 0.002(3) 0.000(3) C551 0.025(5) 0.032(5) 0.028(5) 0.001(4) 0.002(4) 0.000(4) C56 0.032(5) 0.031(5) 0.030(5) 0.000(4) 0.006(4) -0.001(4) O56 0.029(4) 0.013(4) 0.029(4) -0.011(3) -0.001(3) -0.004(3) C561 0.047(6) 0.040(6) 0.041(6) -0.005(4) 0.011(4) -0.005(4) C57 0.029(5) 0.026(5) 0.032(5) -0.002(4) -0.001(4) 0.000(4) C58 0.022(4) 0.018(5) 0.027(5) -0.002(4) 0.005(4) -0.006(4) O58 0.024(3) 0.016(4) 0.022(4) -0.009(3) 0.005(3) 0.001(3) C581 0.031(5) 0.029(5) 0.033(5) -0.002(4) 0.002(4) -0.004(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.384(16) . ? O1 C5 1.527(16) . ? C2 O2 1.150(14) . ? C2 O3 1.337(15) . ? O3 C4 1.486(15) . ? C4 C41 1.470(19) . ? C4 C40 1.489(18) . ? C4 C5 1.523(17) . ? C41 C42 1.18(2) . ? C42 C43 1.46(2) . ? C43 C48 1.412(19) . ? C43 C44 1.46(2) . ? C44 C45 1.37(2) . ? C44 C441 1.49(2) . ? C45 O45 1.387(15) . ? C45 C46 1.403(18) . ? O45 C451 1.429(15) . ? C46 O46 1.342(16) . ? C46 C47 1.401(17) . ? O46 C461 1.404(16) . ? C47 C48 1.388(18) . ? C48 O48 1.319(16) . ? O48 C481 1.416(18) . ? C5 C50 1.442(19) . ? C5 C51 1.453(19) . ? C51 C52 1.248(19) . ? C52 C53 1.373(18) . ? C53 C54 1.350(19) . ? C53 C58 1.385(19) . ? C54 C55 1.45(2) . ? C54 C541 1.49(2) . ? C55 C56 1.34(2) . ? C55 O55 1.378(17) . ? O55 C551 1.433(17) . ? C56 C57 1.33(2) . ? C56 O56 1.406(18) . ? O56 C561 1.41(2) . ? C57 C58 1.41(2) . ? C58 O58 1.397(15) . ? O58 C581 1.391(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C5 108.0(10) . . ? O2 C2 O3 124.8(12) . . ? O2 C2 O1 124.9(12) . . ? O3 C2 O1 110.3(10) . . ? C2 O3 C4 109.2(10) . . ? C41 C4 O3 107.4(10) . . ? C41 C4 C40 109.5(11) . . ? O3 C4 C40 107.8(11) . . ? C41 C4 C5 113.5(11) . . ? O3 C4 C5 102.0(9) . . ? C40 C4 C5 115.9(11) . . ? C42 C41 C4 176.1(14) . . ? C41 C42 C43 177.3(14) . . ? C48 C43 C42 119.1(11) . . ? C48 C43 C44 120.5(12) . . ? C42 C43 C44 120.3(12) . . ? C45 C44 C43 116.9(13) . . ? C45 C44 C441 123.3(13) . . ? C43 C44 C441 119.8(13) . . ? C44 C45 O45 118.1(12) . . ? C44 C45 C46 122.9(11) . . ? O45 C45 C46 119.0(11) . . ? C45 O45 C451 114.5(9) . . ? O46 C46 C47 123.4(11) . . ? O46 C46 C45 117.2(10) . . ? C47 C46 C45 119.4(11) . . ? C46 O46 C461 118.4(10) . . ? C48 C47 C46 120.8(12) . . ? O48 C48 C47 126.2(12) . . ? O48 C48 C43 114.2(11) . . ? C47 C48 C43 119.5(11) . . ? C48 O48 C481 116.4(11) . . ? C50 C5 C51 113.9(11) . . ? C50 C5 C4 118.6(11) . . ? C51 C5 C4 110.1(11) . . ? C50 C5 O1 105.2(10) . . ? C51 C5 O1 107.6(10) . . ? C4 C5 O1 99.6(9) . . ? C52 C51 C5 172.7(13) . . ? C51 C52 C53 178.7(14) . . ? C54 C53 C52 121.8(12) . . ? C54 C53 C58 119.1(12) . . ? C52 C53 C58 119.0(11) . . ? C53 C54 C55 119.9(13) . . ? C53 C54 C541 121.5(13) . . ? C55 C54 C541 118.7(12) . . ? C56 C55 O55 124.0(13) . . ? C56 C55 C54 117.5(13) . . ? O55 C55 C54 118.4(12) . . ? C55 O55 C551 116.2(11) . . ? C57 C56 C55 125.0(15) . . ? C57 C56 O56 122.0(14) . . ? C55 C56 O56 113.1(13) . . ? C56 O56 C561 117.2(11) . . ? C56 C57 C58 117.3(14) . . ? C53 C58 O58 118.0(12) . . ? C53 C58 C57 121.2(12) . . ? O58 C58 C57 120.8(13) . . ? C581 O58 C58 117.9(11) . . ? #===END _database_code_depnum_ccdc_archive 'CCDC 970521'