# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/234 # CIF produced by WinGX routine CIF_UPDATE # Created on 1999-10-13 at 13:36:38 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1beta3 # Request file : c:\wingx\files\archive.dat # CIF files read : cs2-13f1 dreduc struct psi_scan data_cs2-13f1 _audit_creation_date 1999-10-13T13:36:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1beta3 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core2.1beta.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C32 H30 O4' _chemical_formula_structural 'C32 H30 O4' _chemical_formula_sum 'C33 H31 Cl3 O4' _chemical_formula_weight 597.93 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 21.396(8) _cell_length_b 5.699(4) _cell_length_c 24.090(9) _cell_angle_alpha 90 _cell_angle_beta 94.45(5) _cell_angle_gamma 90 _cell_volume 2929(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.219 _cell_measurement_theta_max 8.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour transparent _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.35 _exptl_absorpt_factor_muR 0.053 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 2 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.8997 _exptl_absorpt_correction_T_max 0.9452 _exptl_absorpt_correction_T_ave 0.9245 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.18126E-1 _diffrn_orient_matrix_ub_12 0.36964E-1 _diffrn_orient_matrix_ub_13 -0.38453E-1 _diffrn_orient_matrix_ub_21 -0.43129E-1 _diffrn_orient_matrix_ub_22 -0.12774E-1 _diffrn_orient_matrix_ub_23 0.12852E-1 _diffrn_orient_matrix_ub_31 0.00083 _diffrn_orient_matrix_ub_32 0.170909 _diffrn_orient_matrix_ub_33 0.9297E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_standards_decay_corr_max 1.776 _diffrn_standards_decay_corr_min 0.977 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 8 0 4 10 0 0 _diffrn_reflns_number 4168 _diffrn_reflns_av_R_equivalents 0.1067 _diffrn_reflns_av_sigmaI/netI 0.5339 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 23.03 _diffrn_reflns_theta_full 23.03 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 4056 _reflns_number_gt 1182 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4/PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4/PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97(Sheldrick,1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1998)' #----------------------------------------------------------------------------# # 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^ > 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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4056 _refine_ls_number_parameters 317 _refine_ls_number_restraints 97 _refine_ls_R_factor_all 0.4081 _refine_ls_R_factor_gt 0.1627 _refine_ls_wR_factor_ref 0.5726 _refine_ls_wR_factor_gt 0.4387 _refine_ls_goodness_of_fit_ref 0.915 _refine_ls_restrained_S_all 0.906 _refine_ls_shift/su_max 0.156 _refine_ls_shift/su_mean 0.01 _refine_diff_density_max 0.154 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.032 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 C1 C 0.7357(7) 0.175(4) 0.9604(7) 0.063(5) Uani 1 1 d U . . H1 H 0.7459 0.0207 0.9765 0.076 Uiso 1 1 calc R . . C2 C 0.7621(5) 0.184(2) 0.9036(4) 0.064(5) Uani 1 1 d GU . . C3 C 0.8015(5) 0.0082(17) 0.8869(4) 0.070(6) Uani 1 1 d GU . . H3 H 0.8098 -0.1221 0.9095 0.11(4) Uiso 1 1 calc R . . C4 C 0.8285(5) 0.0267(18) 0.8364(5) 0.068(5) Uani 1 1 d GU . . H4 H 0.8548 -0.0912 0.8253 0.11(4) Uiso 1 1 calc R . . C5 C 0.8161(5) 0.221(2) 0.8026(3) 0.064(5) Uani 1 1 d GU . . C6 C 0.7767(5) 0.3977(17) 0.8193(4) 0.068(6) Uani 1 1 d GU . . H6 H 0.7684 0.528 0.7966 0.11(4) Uiso 1 1 calc R . . C7 C 0.7497(5) 0.3792(18) 0.8697(4) 0.061(5) Uani 1 1 d GU . . H7 H 0.7234 0.4972 0.8809 0.11(4) Uiso 1 1 calc R . . C8 C 0.8448(11) 0.432(4) 0.7215(8) 0.088(7) Uani 1 1 d U . . H8A H 0.803 0.4498 0.7044 0.133 Uiso 1 1 calc R . . H8B H 0.8737 0.4194 0.6932 0.133 Uiso 1 1 calc R . . H8C H 0.8553 0.566 0.7445 0.133 Uiso 1 1 calc R . . C9 C 0.7668(8) 0.365(3) 1.0012(7) 0.066(5) Uani 1 1 d U . . H9 H 0.7566 0.5203 0.9853 0.079 Uiso 1 1 calc R . . C10 C 0.7422(5) 0.357(2) 1.0592(3) 0.059(5) Uani 1 1 d GU . . C11 C 0.7058(5) 0.5398(16) 1.0771(4) 0.065(5) Uani 1 1 d GU . . H11 H 0.6965 0.6674 1.0539 0.07(2) Uiso 1 1 calc R . . C12 C 0.6835(5) 0.5319(17) 1.1297(4) 0.065(5) Uani 1 1 d GU . . H12 H 0.6592 0.6543 1.1417 0.07(2) Uiso 1 1 calc R . . C13 C 0.6975(5) 0.341(2) 1.1644(3) 0.065(5) Uani 1 1 d GU . . C14 C 0.7339(5) 0.1581(18) 1.1465(4) 0.070(5) Uani 1 1 d GU . . H14 H 0.7433 0.0305 1.1697 0.07(2) Uiso 1 1 calc R . . C15 C 0.7563(5) 0.1660(18) 1.0938(4) 0.071(6) Uani 1 1 d GU . . H15 H 0.7806 0.0436 1.0818 0.07(2) Uiso 1 1 calc R . . C16 C 0.6862(11) 0.164(4) 1.2532(9) 0.092(7) Uani 1 1 d U . . H16A H 0.6719 0.0198 1.2361 0.139 Uiso 1 1 calc R . . H16B H 0.6654 0.1895 1.2866 0.139 Uiso 1 1 calc R . . H16C H 0.7307 0.156 1.2622 0.139 Uiso 1 1 calc R . . C17 C 0.6647(7) 0.203(3) 0.9572(8) 0.064(5) Uani 1 1 d U . . H17A H 0.6528 0.3337 0.933 0.077 Uiso 1 1 calc R . . H17B H 0.652 0.2391 0.994 0.077 Uiso 1 1 calc R . . C18 C 0.6294(8) -0.019(3) 0.9353(7) 0.063(5) Uani 1 1 d U . . C19 C 0.5599(4) -0.007(2) 0.9264(5) 0.066(5) Uani 1 1 d GU . . C20 C 0.5304(6) -0.2030(19) 0.9020(5) 0.080(6) Uani 1 1 d GU . . H20 H 0.5542 -0.3264 0.8896 0.16(5) Uiso 1 1 calc R . . C21 C 0.4653(6) -0.214(2) 0.8960(5) 0.091(7) Uani 1 1 d GU . . H21 H 0.4456 -0.3454 0.8796 0.16(5) Uiso 1 1 calc R . . C22 C 0.4298(4) -0.030(3) 0.9144(6) 0.085(6) Uani 1 1 d GU . . H22 H 0.3863 -0.0375 0.9104 0.16(5) Uiso 1 1 calc R . . C23 C 0.4593(5) 0.166(2) 0.9388(5) 0.082(6) Uani 1 1 d GU . . H23 H 0.4355 0.2893 0.9511 0.16(5) Uiso 1 1 calc R . . C24 C 0.5244(5) 0.1772(19) 0.9448(5) 0.072(6) Uani 1 1 d GU . . H24 H 0.5441 0.3082 0.9611 0.16(5) Uiso 1 1 calc R . . C25 C 0.8392(8) 0.337(4) 1.0045(8) 0.068(5) Uani 1 1 d U . . H25A H 0.8509 0.1926 1.024 0.082 Uiso 1 1 calc R . . H25B H 0.8529 0.3256 0.9671 0.082 Uiso 1 1 calc R . . C26 C 0.8718(8) 0.541(4) 1.0343(6) 0.061(5) Uani 1 1 d U . . C27 C 0.9388(4) 0.496(2) 1.0589(5) 0.067(5) Uani 1 1 d GU . . C28 C 0.9718(5) 0.2935(19) 1.0480(5) 0.070(6) Uani 1 1 d GU . . H28 H 0.9527 0.1765 1.0257 0.11(3) Uiso 1 1 calc R . . C29 C 1.0331(5) 0.2655(19) 1.0704(5) 0.074(6) Uani 1 1 d GU . . H29 H 1.0552 0.1298 1.0631 0.11(3) Uiso 1 1 calc R . . C30 C 1.0616(4) 0.440(2) 1.1038(5) 0.082(6) Uani 1 1 d GU . . H30 H 1.1026 0.4217 1.1188 0.11(3) Uiso 1 1 calc R . . C31 C 1.0286(5) 0.643(2) 1.1146(5) 0.081(6) Uani 1 1 d GU . . H31 H 1.0476 0.7604 1.1369 0.11(3) Uiso 1 1 calc R . . C32 C 0.9672(5) 0.6713(19) 1.0922(5) 0.075(6) Uani 1 1 d GU . . H32 H 0.9452 0.8071 1.0995 0.11(3) Uiso 1 1 calc R . . O1 O 0.8480(6) 0.224(3) 0.7551(5) 0.082(5) Uani 1 1 d U . . O2 O 0.6723(6) 0.356(3) 1.2150(5) 0.075(5) Uani 1 1 d U . . O3 O 0.6587(5) -0.197(2) 0.9277(6) 0.081(5) Uani 1 1 d U . . O4 O 0.8481(6) 0.729(2) 1.0389(7) 0.090(6) Uani 1 1 d U . . C33A C 0.9528(18) 0.096(8) 1.2523(16) 0.072(11) Uiso 0.5 1 d PDU A 1 Cl1A Cl 0.8999(9) 0.169(4) 1.1858(8) 0.114(8) Uiso 0.5 1 d PDU A 1 Cl2A Cl 1.0300(8) 0.010(3) 1.2441(6) 0.100(6) Uiso 0.5 1 d PDU A 1 Cl3A Cl 0.9556(6) 0.337(3) 1.2950(5) 0.094(5) Uiso 0.5 1 d PDU A 1 C33B C 0.963(3) 0.217(15) 1.228(3) 0.16(3) Uiso 0.5 1 d PDU B 2 Cl1B Cl 0.9205(8) 0.176(3) 1.1840(6) 0.093(6) Uiso 0.5 1 d PDU B 2 Cl2B Cl 1.0096(16) -0.050(7) 1.2427(14) 0.221(17) Uiso 0.5 1 d PDU B 2 Cl3B Cl 0.9708(10) 0.434(5) 1.2712(9) 0.166(8) Uiso 0.5 1 d PDU B 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 C1 0.061(8) 0.060(10) 0.068(8) 0.007(7) -0.001(6) 0.001(7) C2 0.060(10) 0.059(9) 0.071(8) -0.002(7) 0.001(7) -0.011(8) C3 0.059(11) 0.083(12) 0.067(9) 0.011(9) -0.004(7) 0.011(9) C4 0.075(12) 0.058(10) 0.071(9) -0.011(7) 0.000(7) 0.001(9) C5 0.070(11) 0.072(11) 0.048(8) -0.011(7) -0.001(6) 0.006(8) C6 0.067(11) 0.063(11) 0.073(10) 0.000(8) 0.005(7) -0.001(8) C7 0.058(10) 0.060(10) 0.063(9) -0.010(7) 0.002(7) -0.004(8) C8 0.110(16) 0.093(15) 0.062(11) 0.004(10) 0.007(10) 0.004(14) C9 0.067(8) 0.059(11) 0.071(8) 0.000(7) 0.003(7) 0.000(8) C10 0.053(9) 0.052(9) 0.072(8) -0.001(6) 0.000(6) -0.003(7) C11 0.069(11) 0.051(9) 0.073(9) -0.009(8) 0.003(7) -0.008(8) C12 0.073(11) 0.051(9) 0.071(9) -0.008(7) 0.005(7) -0.016(8) C13 0.067(11) 0.063(10) 0.066(8) -0.005(7) 0.003(7) -0.011(8) C14 0.069(11) 0.073(11) 0.068(9) 0.003(9) 0.002(7) 0.003(9) C15 0.074(12) 0.066(11) 0.072(9) 0.007(8) 0.004(8) 0.007(9) C16 0.111(16) 0.089(15) 0.078(11) 0.022(11) 0.009(11) -0.002(14) C17 0.059(8) 0.046(8) 0.086(12) 0.019(9) 0.007(7) 0.000(7) C18 0.060(7) 0.057(9) 0.073(11) -0.005(9) 0.020(8) -0.002(6) C19 0.063(7) 0.060(10) 0.073(11) 0.002(9) 0.003(8) 0.001(6) C20 0.084(9) 0.075(11) 0.080(12) 0.008(10) -0.004(9) -0.013(9) C21 0.085(10) 0.092(14) 0.093(14) -0.009(12) 0.001(11) -0.026(10) C22 0.090(12) 0.078(12) 0.085(14) 0.027(11) 0.003(10) -0.013(8) C23 0.066(8) 0.096(14) 0.082(12) -0.005(12) -0.001(9) 0.008(9) C24 0.066(8) 0.075(11) 0.074(11) 0.010(10) 0.002(8) 0.015(8) C25 0.063(8) 0.058(10) 0.083(11) -0.007(9) 0.007(7) -0.002(8) C26 0.066(8) 0.074(10) 0.046(9) -0.013(9) 0.010(6) 0.004(7) C27 0.065(9) 0.066(10) 0.070(11) 0.010(9) 0.003(7) -0.008(6) C28 0.066(9) 0.067(10) 0.075(11) 0.005(9) -0.007(8) -0.004(8) C29 0.065(9) 0.071(12) 0.083(12) 0.007(9) -0.004(8) -0.006(8) C30 0.074(12) 0.093(14) 0.077(12) 0.000(11) -0.016(9) -0.001(9) C31 0.076(11) 0.079(12) 0.087(13) -0.010(11) 0.001(9) -0.021(9) C32 0.071(9) 0.090(13) 0.065(11) -0.011(10) 0.008(7) -0.003(9) O1 0.094(9) 0.081(10) 0.072(8) 0.001(7) 0.017(6) 0.008(8) O2 0.084(9) 0.079(9) 0.063(7) -0.002(6) 0.009(5) -0.003(7) O3 0.064(8) 0.054(7) 0.126(11) -0.009(8) 0.005(7) 0.003(6) O4 0.087(10) 0.059(8) 0.120(12) -0.015(8) -0.007(8) 0.003(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.522(18) . ? C1 C17 1.52(2) . ? C1 C9 1.58(3) . ? C1 H1 0.98 . ? C2 C3 1.39 . ? C2 C7 1.39 . ? C3 C4 1.39 . ? C3 H3 0.93 . ? C4 C5 1.39 . ? C4 H4 0.93 . ? C5 O1 1.377(14) . ? C5 C6 1.39 . ? C6 C7 1.39 . ? C6 H6 0.93 . ? C7 H7 0.93 . ? C8 O1 1.43(2) . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? C9 C10 1.530(19) . ? C9 C25 1.55(2) . ? C9 H9 0.98 . ? C10 C11 1.39 . ? C10 C15 1.39 . ? C11 C12 1.39 . ? C11 H11 0.93 . ? C12 C13 1.39 . ? C12 H12 0.93 . ? C13 O2 1.375(14) . ? C13 C14 1.39 . ? C14 C15 1.39 . ? C14 H14 0.93 . ? C15 H15 0.93 . ? C16 O2 1.45(2) . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C17 C18 1.54(2) . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? C18 O3 1.21(2) . ? C18 C19 1.486(19) . ? C19 C20 1.39 . ? C19 C24 1.39 . ? C20 C21 1.39 . ? C20 H20 0.93 . ? C21 C22 1.39 . ? C21 H21 0.93 . ? C22 C23 1.39 . ? C22 H22 0.93 . ? C23 C24 1.39 . ? C23 H23 0.93 . ? C24 H24 0.93 . ? C25 C26 1.51(3) . ? C25 H25A 0.97 . ? C25 H25B 0.97 . ? C26 O4 1.20(2) . ? C26 C27 1.529(19) . ? C27 C28 1.39 . ? C27 C32 1.39 . ? C28 C29 1.39 . ? C28 H28 0.93 . ? C29 C30 1.39 . ? C29 H29 0.93 . ? C30 C31 1.39 . ? C30 H30 0.93 . ? C31 C32 1.39 . ? C31 H31 0.93 . ? C32 H32 0.93 . ? C33A Cl3A 1.71(4) . ? C33A Cl2A 1.75(4) . ? C33A Cl1A 1.93(4) . ? C33B Cl1B 1.36(7) . ? C33B Cl3B 1.62(7) . ? C33B Cl2B 1.84(8) . ? 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 C1 C17 112.9(13) . . ? C2 C1 C9 111.7(14) . . ? C17 C1 C9 109.4(15) . . ? C2 C1 H1 107.5 . . ? C17 C1 H1 107.5 . . ? C9 C1 H1 107.5 . . ? C3 C2 C7 120 . . ? C3 C2 C1 120.7(10) . . ? C7 C2 C1 119.2(10) . . ? C2 C3 C4 120 . . ? C2 C3 H3 120 . . ? C4 C3 H3 120 . . ? C5 C4 C3 120 . . ? C5 C4 H4 120 . . ? C3 C4 H4 120 . . ? O1 C5 C6 125.7(10) . . ? O1 C5 C4 114.3(10) . . ? C6 C5 C4 120 . . ? C5 C6 C7 120 . . ? C5 C6 H6 120 . . ? C7 C6 H6 120 . . ? C6 C7 C2 120 . . ? C6 C7 H7 120 . . ? C2 C7 H7 120 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C25 111.3(13) . . ? C10 C9 C1 112.9(14) . . ? C25 C9 C1 109.3(14) . . ? C10 C9 H9 107.7 . . ? C25 C9 H9 107.7 . . ? C1 C9 H9 107.7 . . ? C11 C10 C15 120 . . ? C11 C10 C9 120.0(10) . . ? C15 C10 C9 120.0(10) . . ? C10 C11 C12 120 . . ? C10 C11 H11 120 . . ? C12 C11 H11 120 . . ? C13 C12 C11 120 . . ? C13 C12 H12 120 . . ? C11 C12 H12 120 . . ? O2 C13 C12 113.7(10) . . ? O2 C13 C14 126.3(10) . . ? C12 C13 C14 120 . . ? C13 C14 C15 120 . . ? C13 C14 H14 120 . . ? C15 C14 H14 120 . . ? C14 C15 C10 120 . . ? C14 C15 H15 120 . . ? C10 C15 H15 120 . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C1 C17 C18 113.3(15) . . ? C1 C17 H17A 108.9 . . ? C18 C17 H17A 108.9 . . ? C1 C17 H17B 108.9 . . ? C18 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? O3 C18 C19 122.5(16) . . ? O3 C18 C17 119.3(16) . . ? C19 C18 C17 118.2(14) . . ? C20 C19 C24 120 . . ? C20 C19 C18 116.3(10) . . ? C24 C19 C18 123.5(11) . . ? C19 C20 C21 120 . . ? C19 C20 H20 120 . . ? C21 C20 H20 120 . . ? C22 C21 C20 120 . . ? C22 C21 H21 120 . . ? C20 C21 H21 120 . . ? C21 C22 C23 120 . . ? C21 C22 H22 120 . . ? C23 C22 H22 120 . . ? C24 C23 C22 120 . . ? C24 C23 H23 120 . . ? C22 C23 H23 120 . . ? C23 C24 C19 120 . . ? C23 C24 H24 120 . . ? C19 C24 H24 120 . . ? C26 C25 C9 111.4(16) . . ? C26 C25 H25A 109.3 . . ? C9 C25 H25A 109.3 . . ? C26 C25 H25B 109.3 . . ? C9 C25 H25B 109.3 . . ? H25A C25 H25B 108 . . ? O4 C26 C25 123.5(17) . . ? O4 C26 C27 120.4(17) . . ? C25 C26 C27 116.1(16) . . ? C28 C27 C32 120 . . ? C28 C27 C26 122.7(10) . . ? C32 C27 C26 117.3(10) . . ? C27 C28 C29 120 . . ? C27 C28 H28 120 . . ? C29 C28 H28 120 . . ? C30 C29 C28 120 . . ? C30 C29 H29 120 . . ? C28 C29 H29 120 . . ? C29 C30 C31 120 . . ? C29 C30 H30 120 . . ? C31 C30 H30 120 . . ? C32 C31 C30 120 . . ? C32 C31 H31 120 . . ? C30 C31 H31 120 . . ? C31 C32 C27 120 . . ? C31 C32 H32 120 . . ? C27 C32 H32 120 . . ? C5 O1 C8 118.1(14) . . ? C13 O2 C16 116.1(14) . . ? Cl3A C33A Cl2A 108(2) . . ? Cl3A C33A Cl1A 108(2) . . ? Cl2A C33A Cl1A 118(2) . . ? Cl1B C33B Cl3B 132(6) . . ? Cl1B C33B Cl2B 109(5) . . ? Cl3B C33B Cl2B 118(4) . . ? # CIF produced by WinGX routine CIF_UPDATE # Created on 1999-10-13 at 14:02:54 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1beta3 # Request file : c:\wingx\files\archive.dat # CIF files read : cs2-13f2 dreduc struct psi_scan data_cs2-13f2 _audit_creation_date 1999-10-13T14:02:54-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1beta3 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core2.1beta.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C32 H30 O4' _chemical_formula_structural 'C32 H30 O4' _chemical_formula_sum 'C32 H30 O4' _chemical_formula_weight 478.56 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.431(5) _cell_length_b 6.0470(10) _cell_length_c 18.286(6) _cell_angle_alpha 90 _cell_angle_beta 96.69(7) _cell_angle_gamma 90 _cell_volume 1255.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour transparent _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_factor_muR 0.009 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_correction_T_ave 0.9562 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.56482E-1 _diffrn_orient_matrix_ub_12 -0.00967 _diffrn_orient_matrix_ub_13 0.45996E-1 _diffrn_orient_matrix_ub_21 0.67382E-1 _diffrn_orient_matrix_ub_22 -0.00468 _diffrn_orient_matrix_ub_23 -0.30274E-1 _diffrn_orient_matrix_ub_31 0.5164E-2 _diffrn_orient_matrix_ub_32 0.164848 _diffrn_orient_matrix_ub_33 0.1896E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_standards_decay_corr_max 1.023 _diffrn_standards_decay_corr_min 0.964 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 0 -7 6 0 2 _diffrn_reflns_number 2505 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.1106 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 2426 _reflns_number_gt 1383 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4/PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4/PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1998)' #----------------------------------------------------------------------------# # 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^ > 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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.008(2) _refine_ls_number_reflns 2426 _refine_ls_number_parameters 350 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1431 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1443 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 0.876 _refine_ls_restrained_S_all 0.876 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(3) _refine_diff_density_max 0.212 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # 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 0.2977(4) 0.3491(8) 0.6486(3) 0.0426(13) Uani 1 1 d . . . O2 O -0.1610(4) 0.6461(10) 0.9626(2) 0.0537(14) Uani 1 1 d . . . O3 O -0.3297(3) 0.8741(8) 0.5037(2) 0.0448(13) Uani 1 1 d . . . O4 O 0.2192(4) 0.1922(8) 0.7899(3) 0.0464(12) Uani 1 1 d . . . C1 C 0.2530(5) 0.5569(11) 0.7515(3) 0.0300(15) Uani 1 1 d . . . C2 C 0.3086(5) 0.5699(11) 0.6771(3) 0.0341(16) Uani 1 1 d . . . C3 C 0.2240(5) 0.7285(12) 0.6302(3) 0.0399(17) Uani 1 1 d . . . H3A H 0.2639 0.8663 0.622 0.040(13) Uiso 1 1 calc R . . H3B H 0.1984 0.6621 0.5827 0.040(13) Uiso 1 1 calc R . . C4 C 0.1173(5) 0.7728(12) 0.6719(3) 0.0346(16) Uani 1 1 d . . . C5 C 0.1208(5) 0.5786(12) 0.7270(3) 0.0331(16) Uani 1 1 d . . . H5 H 0.0949 0.445 0.6994 0.041(19) Uiso 1 1 calc R . . C7 C 0.0449(5) 0.6053(11) 0.7889(3) 0.0337(16) Uani 1 1 d . . . C8 C 0.0568(6) 0.7839(12) 0.8366(3) 0.0449(18) Uani 1 1 d . . . H8 H 0.1119 0.8927 0.8295 0.047(14) Uiso 1 1 calc R . . C9 C -0.0107(5) 0.8064(12) 0.8947(3) 0.0421(17) Uani 1 1 d . . . H9 H -0.0005 0.9281 0.9259 0.047(14) Uiso 1 1 calc R . . C10 C -0.0929(5) 0.6467(13) 0.9056(3) 0.0376(17) Uani 1 1 d . . . C11 C -0.1066(6) 0.4700(14) 0.8583(4) 0.0465(19) Uani 1 1 d . . . H11 H -0.1619 0.3615 0.8653 0.054(15) Uiso 1 1 calc R . . C12 C -0.0401(5) 0.4505(13) 0.8009(4) 0.0421(19) Uani 1 1 d . . . H12 H -0.0525 0.3304 0.7692 0.054(15) Uiso 1 1 calc R . . C13 C -0.1574(6) 0.8325(15) 1.0086(4) 0.060(2) Uani 1 1 d . . . H13A H -0.2197 0.8234 1.0394 0.079(15) Uiso 1 1 calc R . . H13B H -0.167 0.9638 0.9791 0.079(15) Uiso 1 1 calc R . . H13C H -0.0829 0.8375 1.0389 0.079(15) Uiso 1 1 calc R . . C14 C 0.0006(5) 0.8027(11) 0.6247(3) 0.0310(15) Uani 1 1 d . . . C15 C -0.0617(6) 0.9933(12) 0.6303(3) 0.0417(18) Uani 1 1 d . . . H15 H -0.0289 1.1046 0.6613 0.058(16) Uiso 1 1 calc R . . C16 C -0.1725(6) 1.0278(13) 0.5916(3) 0.0435(18) Uani 1 1 d . . . H16 H -0.2135 1.1586 0.5968 0.058(16) Uiso 1 1 calc R . . C17 C -0.2197(5) 0.8623(13) 0.5451(3) 0.0387(17) Uani 1 1 d . . . C18 C -0.1564(6) 0.6715(13) 0.5365(4) 0.0458(19) Uani 1 1 d . . . H18 H -0.1878 0.5619 0.5043 0.058(16) Uiso 1 1 calc R . . C19 C -0.0462(6) 0.6432(13) 0.5759(3) 0.0439(18) Uani 1 1 d . . . H19 H -0.0034 0.5154 0.5692 0.058(16) Uiso 1 1 calc R . . C20 C -0.4062(6) 1.0475(15) 0.5206(4) 0.059(2) Uani 1 1 d . . . H20A H -0.4805 1.0328 0.4907 0.060(13) Uiso 1 1 calc R . . H20B H -0.3715 1.1875 0.511 0.060(13) Uiso 1 1 calc R . . H20C H -0.4181 1.0392 0.5716 0.060(13) Uiso 1 1 calc R . . C21 C 0.4367(5) 0.6457(12) 0.6878(3) 0.0354(16) Uani 1 1 d . . . C22 C 0.4657(5) 0.8572(12) 0.7117(3) 0.0371(16) Uani 1 1 d . . . H22 H 0.4065 0.9609 0.7151 0.049(9) Uiso 1 1 calc R . . C23 C 0.5823(6) 0.9164(13) 0.7306(4) 0.049(2) Uani 1 1 d . . . H23 H 0.6004 1.0573 0.7489 0.049(9) Uiso 1 1 calc R . . C24 C 0.6714(7) 0.7699(17) 0.7226(4) 0.063(3) Uani 1 1 d . . . H24 H 0.7496 0.8114 0.7349 0.049(9) Uiso 1 1 calc R . . C25 C 0.6445(7) 0.5634(16) 0.6966(4) 0.057(2) Uani 1 1 d . . . H25 H 0.7046 0.4644 0.6901 0.049(9) Uiso 1 1 calc R . . C26 C 0.5279(6) 0.4991(13) 0.6795(3) 0.0429(18) Uani 1 1 d . . . H26 H 0.5106 0.3566 0.6623 0.049(9) Uiso 1 1 calc R . . C27 C 0.2860(5) 0.3518(12) 0.7960(3) 0.0329(15) Uani 1 1 d . . . C29 C 0.4247(6) 0.1382(12) 0.8837(3) 0.0395(17) Uani 1 1 d . . . H29 H 0.3729 0.0194 0.8772 0.046(9) Uiso 1 1 calc R . . C30 C 0.5298(6) 0.1175(13) 0.9296(4) 0.0501(19) Uani 1 1 d . . . H30 H 0.548 -0.015 0.9541 0.046(9) Uiso 1 1 calc R . . C31 C 0.6067(6) 0.2922(13) 0.9388(4) 0.0468(19) Uani 1 1 d . . . H31 H 0.6777 0.2765 0.9689 0.046(9) Uiso 1 1 calc R . . C32 C 0.5799(6) 0.4880(13) 0.9044(4) 0.0415(18) Uani 1 1 d . . . H32 H 0.6323 0.606 0.9114 0.046(9) Uiso 1 1 calc R . . C33 C 0.4755(5) 0.5123(11) 0.8593(3) 0.0340(16) Uani 1 1 d . . . H33 H 0.4571 0.6473 0.8364 0.046(9) Uiso 1 1 calc R . . C28 C 0.3973(5) 0.3356(11) 0.8478(3) 0.0315(15) Uani 1 1 d . . . H1 H 0.276(4) 0.692(8) 0.783(2) 0.004(12) Uiso 1 1 d . . . H4 H 0.133(4) 0.904(9) 0.704(3) 0.015(14) Uiso 1 1 d . . . H01 H 0.302(7) 0.362(17) 0.605(4) 0.08(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.065(3) 0.028(3) 0.035(3) -0.006(2) 0.005(2) -0.009(3) O2 0.045(3) 0.074(4) 0.046(3) -0.017(3) 0.021(2) -0.014(3) O3 0.033(2) 0.060(4) 0.040(2) 0.001(3) -0.002(2) 0.006(3) O4 0.047(3) 0.035(3) 0.055(3) 0.004(2) -0.001(2) -0.019(3) C1 0.033(3) 0.025(4) 0.032(3) -0.001(3) 0.001(3) -0.007(3) C2 0.039(4) 0.030(4) 0.033(3) -0.001(3) 0.005(3) -0.002(3) C3 0.041(4) 0.042(4) 0.036(3) 0.007(3) 0.002(3) -0.010(4) C4 0.039(4) 0.038(4) 0.026(3) -0.002(3) 0.000(3) -0.011(3) C5 0.032(3) 0.034(4) 0.033(3) 0.002(3) 0.002(3) -0.009(3) C7 0.032(3) 0.040(4) 0.028(3) 0.000(3) -0.001(3) -0.002(3) C8 0.053(4) 0.034(5) 0.050(4) -0.006(4) 0.015(3) -0.011(4) C9 0.049(4) 0.036(4) 0.042(4) -0.013(4) 0.007(3) -0.010(4) C10 0.026(3) 0.047(5) 0.040(4) -0.007(4) 0.007(3) 0.000(3) C11 0.035(4) 0.054(5) 0.054(4) -0.014(4) 0.018(3) -0.020(4) C12 0.032(4) 0.048(5) 0.047(4) -0.009(4) 0.007(3) -0.013(4) C13 0.061(5) 0.070(6) 0.054(4) -0.016(5) 0.029(4) -0.002(5) C14 0.035(4) 0.026(4) 0.032(3) -0.004(3) 0.003(3) 0.004(3) C15 0.049(4) 0.036(4) 0.037(4) -0.006(4) -0.003(3) 0.001(4) C16 0.053(5) 0.033(4) 0.044(4) -0.006(4) 0.004(3) 0.015(4) C17 0.036(4) 0.048(5) 0.032(3) 0.008(4) 0.004(3) 0.000(4) C18 0.051(4) 0.035(4) 0.048(4) -0.006(4) -0.007(4) 0.002(4) C19 0.050(4) 0.034(4) 0.045(4) -0.007(4) -0.005(3) 0.003(4) C20 0.040(4) 0.083(7) 0.052(4) -0.007(5) 0.000(3) 0.024(5) C21 0.040(4) 0.041(4) 0.025(3) 0.006(3) 0.005(3) 0.000(4) C22 0.034(4) 0.035(4) 0.044(4) 0.010(4) 0.010(3) -0.002(3) C23 0.052(5) 0.046(5) 0.049(4) 0.014(4) 0.005(4) -0.018(4) C24 0.040(5) 0.083(7) 0.068(5) 0.026(6) 0.008(4) -0.012(5) C25 0.038(4) 0.069(7) 0.067(5) 0.008(5) 0.019(4) 0.017(4) C26 0.044(4) 0.038(5) 0.049(4) 0.004(4) 0.016(3) 0.007(4) C27 0.042(4) 0.030(4) 0.027(3) -0.001(3) 0.006(3) 0.000(4) C29 0.042(4) 0.035(4) 0.041(4) 0.000(4) 0.002(3) 0.001(4) C30 0.062(5) 0.037(5) 0.051(4) 0.016(4) 0.010(4) 0.006(4) C31 0.040(4) 0.057(6) 0.042(4) 0.008(4) -0.002(3) 0.008(4) C32 0.039(4) 0.042(5) 0.042(4) 0.006(4) -0.001(3) -0.007(4) C33 0.042(4) 0.028(4) 0.033(3) 0.004(3) 0.007(3) 0.002(3) C28 0.039(4) 0.026(4) 0.031(3) 0.002(3) 0.012(3) -0.005(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 1.434(8) . ? O1 H01 0.80(7) . ? O2 C10 1.371(7) . ? O2 C13 1.404(9) . ? O3 C17 1.393(7) . ? O3 C20 1.422(8) . ? O4 C27 1.228(8) . ? C1 C27 1.507(9) . ? C1 C5 1.532(8) . ? C1 C2 1.569(8) . ? C1 H1 1.02(5) . ? C2 C21 1.525(8) . ? C2 C3 1.548(9) . ? C3 C4 1.535(9) . ? C3 H3A 0.97 . ? C3 H3B 0.97 . ? C4 C14 1.512(8) . ? C4 C5 1.544(8) . ? C4 H4 0.99(5) . ? C5 C7 1.513(8) . ? C5 H5 0.98 . ? C7 C8 1.385(9) . ? C7 C12 1.385(9) . ? C8 C9 1.391(9) . ? C8 H8 0.93 . ? C9 C10 1.378(9) . ? C9 H9 0.93 . ? C10 C11 1.373(10) . ? C11 C12 1.371(8) . ? C11 H11 0.93 . ? C12 H12 0.93 . ? C13 H13A 0.96 . ? C13 H13B 0.96 . ? C13 H13C 0.96 . ? C14 C15 1.365(9) . ? C14 C19 1.380(9) . ? C15 C16 1.392(9) . ? C15 H15 0.93 . ? C16 C17 1.381(10) . ? C16 H16 0.93 . ? C17 C18 1.380(10) . ? C18 C19 1.387(9) . ? C18 H18 0.93 . ? C19 H19 0.93 . ? C20 H20A 0.96 . ? C20 H20B 0.96 . ? C20 H20C 0.96 . ? C21 C22 1.380(10) . ? C21 C26 1.390(9) . ? C22 C23 1.384(9) . ? C22 H22 0.93 . ? C23 C24 1.371(11) . ? C23 H23 0.93 . ? C24 C25 1.359(12) . ? C24 H24 0.93 . ? C25 C26 1.389(10) . ? C25 H25 0.93 . ? C26 H26 0.93 . ? C27 C28 1.498(8) . ? C29 C28 1.381(9) . ? C29 C30 1.388(9) . ? C29 H29 0.93 . ? C30 C31 1.372(10) . ? C30 H30 0.93 . ? C31 C32 1.359(10) . ? C31 H31 0.93 . ? C32 C33 1.378(9) . ? C32 H32 0.93 . ? C33 C28 1.393(9) . ? C33 H33 0.93 . ? 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 H01 105(8) . . ? C10 O2 C13 118.3(6) . . ? C17 O3 C20 117.3(5) . . ? C27 C1 C5 113.9(5) . . ? C27 C1 C2 114.1(5) . . ? C5 C1 C2 103.2(5) . . ? C27 C1 H1 109(2) . . ? C5 C1 H1 106(2) . . ? C2 C1 H1 110(3) . . ? O1 C2 C21 111.6(5) . . ? O1 C2 C3 110.7(5) . . ? C21 C2 C3 114.4(5) . . ? O1 C2 C1 104.0(5) . . ? C21 C2 C1 112.6(5) . . ? C3 C2 C1 102.8(5) . . ? C4 C3 C2 108.3(5) . . ? C4 C3 H3A 110 . . ? C2 C3 H3A 110 . . ? C4 C3 H3B 110 . . ? C2 C3 H3B 110 . . ? H3A C3 H3B 108.4 . . ? C14 C4 C3 115.9(5) . . ? C14 C4 C5 114.6(5) . . ? C3 C4 C5 103.3(5) . . ? C14 C4 H4 109(3) . . ? C3 C4 H4 110(3) . . ? C5 C4 H4 103(3) . . ? C7 C5 C1 115.0(5) . . ? C7 C5 C4 115.7(6) . . ? C1 C5 C4 101.9(5) . . ? C7 C5 H5 107.9 . . ? C1 C5 H5 107.9 . . ? C4 C5 H5 107.9 . . ? C8 C7 C12 116.5(6) . . ? C8 C7 C5 122.1(6) . . ? C12 C7 C5 121.4(6) . . ? C7 C8 C9 122.3(6) . . ? C7 C8 H8 118.8 . . ? C9 C8 H8 118.8 . . ? C10 C9 C8 119.4(6) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? O2 C10 C11 116.4(6) . . ? O2 C10 C9 124.7(6) . . ? C11 C10 C9 118.9(6) . . ? C12 C11 C10 121.1(7) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C7 121.7(7) . . ? C11 C12 H12 119.2 . . ? C7 C12 H12 119.2 . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 118.2(6) . . ? C15 C14 C4 119.5(6) . . ? C19 C14 C4 122.3(6) . . ? C14 C15 C16 122.7(6) . . ? C14 C15 H15 118.7 . . ? C16 C15 H15 118.7 . . ? C17 C16 C15 118.1(7) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C18 C17 C16 120.2(6) . . ? C18 C17 O3 115.7(7) . . ? C16 C17 O3 124.1(7) . . ? C17 C18 C19 120.0(7) . . ? C17 C18 H18 120 . . ? C19 C18 H18 120 . . ? C14 C19 C18 120.6(7) . . ? C14 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C26 118.0(6) . . ? C22 C21 C2 120.7(6) . . ? C26 C21 C2 121.0(6) . . ? C21 C22 C23 120.5(7) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 120.8(8) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C25 C24 C23 119.4(8) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 120.6(8) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 120.6(7) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? O4 C27 C28 118.7(6) . . ? O4 C27 C1 118.9(6) . . ? C28 C27 C1 122.4(6) . . ? C28 C29 C30 119.9(7) . . ? C28 C29 H29 120.1 . . ? C30 C29 H29 120.1 . . ? C31 C30 C29 120.1(7) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C32 C31 C30 120.5(6) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C31 C32 C33 120.2(7) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? C32 C33 C28 120.3(6) . . ? C32 C33 H33 119.8 . . ? C28 C33 H33 119.8 . . ? C29 C28 C33 119.0(6) . . ? C29 C28 C27 119.1(6) . . ? C33 C28 C27 121.9(6) . . ?