# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Whiting, Andrew' 'Hawkes, G.' 'Kroemer, Romano T.' 'Liedl, Klaus R.' 'Loerting, Thomas' 'Pritchard, R.' 'Steele, Melanie' 'Thirsk, Carl' 'Warren, John E.' _publ_contact_author_name 'Dr Andrew Whiting' _publ_contact_author_address ; Department of Chemistry Durham University South Road Science laboratories Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email 'ANDY.WHITING@DURHAM.AC.UK' _publ_section_title ; The structure, modelling and dynamics of 2,7-diisopropoxy-1,8-diarylnaphthalenes. ; data_babs _database_code_CSD 178815 _audit_creation_date 2002-01-28T18:24:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H10 Br2 O4' _chemical_formula_sum 'C14 H10 Br2 O4' _chemical_formula_weight 402.04 _chemical_melting_point 452-455 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 21.383(3) _cell_length_b 5.411(2) _cell_length_c 23.737(2) _cell_angle_alpha 90 _cell_angle_beta 96.90(3) _cell_angle_gamma 90 _cell_volume 2726.6(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(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 colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.959 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.955 _exptl_absorpt_factor_muR 0.894 _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 0.1992 _exptl_absorpt_correction_T_max 0.3822 _exptl_absorpt_correction_T_ave 0.3192 #----------------------------------------------------------------------------# # 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_radiation_probe x-ray _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 0.44382E-1 _diffrn_orient_matrix_ub_12 -0.12777E-1 _diffrn_orient_matrix_ub_13 -0.9031E-2 _diffrn_orient_matrix_ub_21 -0.15196E-1 _diffrn_orient_matrix_ub_22 0.14455E-1 _diffrn_orient_matrix_ub_23 -0.41376E-1 _diffrn_orient_matrix_ub_31 0.4224E-2 _diffrn_orient_matrix_ub_32 0.183992 _diffrn_orient_matrix_ub_33 0.2679E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_standards_decay_corr_max 1.006 _diffrn_standards_decay_corr_min 0.947 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 1 -9 -6 2 -2 3 -1 -14 _diffrn_reflns_av_R_equivalents 0.119 _diffrn_reflns_av_unetI/netI 0.1028 _diffrn_reflns_number 2460 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2391 _reflns_number_gt 1332 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1097P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2391 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1391 _refine_ls_R_factor_gt 0.0738 _refine_ls_wR_factor_ref 0.1945 _refine_ls_wR_factor_gt 0.1669 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.826 _refine_diff_density_min -1.191 _refine_diff_density_rms 0.169 #----------------------------------------------------------------------------# # 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' Br Br -0.2901 2.4595 '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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.04212(6) -0.0073(3) 0.08423(6) 0.0522(4) Uani 1 d . . . Br8 Br 0.03942(5) 0.3904(2) 0.18400(5) 0.0455(4) Uani 1 d . . . O1 O 0.1403(3) -0.2419(14) 0.0321(3) 0.0406(19) Uani 1 d . . . O4 O 0.1200(4) -0.0323(16) -0.0482(4) 0.054(2) Uani 1 d . . . O7 O 0.1220(3) 0.7908(14) 0.2287(3) 0.0391(19) Uani 1 d . . . O12 O 0.1431(4) 0.5419(15) 0.3042(3) 0.046(2) Uani 1 d . . . C1 C 0.1267(5) 0.104(2) 0.0921(4) 0.033(3) Uani 1 d . . . C2 C 0.1642(5) -0.032(2) 0.0597(4) 0.034(3) Uani 1 d . . . C3 C 0.2262(6) 0.032(2) 0.0559(5) 0.050(3) Uani 1 d . . . H3 H 0.2503 -0.0582 0.0332 0.06 Uiso 1 calc R . . C4 C 0.2508(5) 0.226(2) 0.0855(5) 0.045(3) Uani 1 d . . . H4 H 0.2914 0.277 0.0808 0.055 Uiso 1 calc R . . C5 C 0.2462(5) 0.557(2) 0.1541(5) 0.039(3) Uani 1 d . . . H5 H 0.2874 0.5975 0.1491 0.047 Uiso 1 calc R . . C6 C 0.2164(5) 0.691(2) 0.1905(4) 0.037(3) Uani 1 d . . . H6 H 0.2363 0.8199 0.2115 0.044 Uiso 1 calc R . . C7 C 0.1527(5) 0.627(2) 0.1951(4) 0.037(3) Uani 1 d . . . C8 C 0.1219(4) 0.4399(19) 0.1672(4) 0.029(3) Uani 1 d . . . C9 C 0.1523(4) 0.293(2) 0.1276(4) 0.027(2) Uani 1 d . . . C10 C 0.2169(4) 0.356(2) 0.1236(4) 0.033(3) Uani 1 d . . . C11 C 0.1176(5) -0.222(2) -0.0232(5) 0.035(3) Uani 1 d . . . C12 C 0.1193(5) 0.717(2) 0.2843(5) 0.040(3) Uani 1 d . . . C13 C 0.0884(6) -0.460(2) -0.0453(6) 0.055(4) Uani 1 d . . . H13A H 0.0476 -0.4782 -0.0326 0.082 Uiso 1 calc R . . H13B H 0.1148 -0.5959 -0.0314 0.082 Uiso 1 calc R . . H13C H 0.084 -0.4593 -0.086 0.082 Uiso 1 calc R . . C14 C 0.0817(5) 0.907(2) 0.3109(5) 0.042(3) Uani 1 d . . . H14A H 0.0848 0.8786 0.3511 0.063 Uiso 1 calc R . . H14B H 0.0384 0.8963 0.2948 0.063 Uiso 1 calc R . . H14C H 0.0977 1.0687 0.304 0.063 Uiso 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 Br1 0.0469(7) 0.0548(9) 0.0571(8) -0.0074(7) 0.0150(6) -0.0094(6) Br8 0.0421(6) 0.0521(8) 0.0463(7) -0.0048(6) 0.0219(5) -0.0013(6) O1 0.064(5) 0.026(5) 0.032(4) 0.005(4) 0.006(4) 0.004(4) O4 0.080(6) 0.032(5) 0.047(5) 0.007(4) 0.001(4) -0.007(5) O7 0.054(5) 0.034(5) 0.032(4) -0.001(4) 0.014(4) 0.011(4) O12 0.066(5) 0.039(6) 0.034(5) 0.012(4) 0.012(4) 0.016(4) C1 0.040(6) 0.030(6) 0.031(6) 0.016(6) 0.007(5) 0.006(5) C2 0.046(6) 0.028(7) 0.030(6) 0.002(5) 0.010(5) 0.012(5) C3 0.051(7) 0.057(10) 0.045(7) -0.011(7) 0.016(6) 0.013(7) C4 0.048(7) 0.050(9) 0.042(7) 0.003(7) 0.023(6) 0.011(6) C5 0.041(6) 0.043(8) 0.038(6) 0.003(6) 0.021(5) -0.002(5) C6 0.048(7) 0.037(7) 0.028(6) 0.006(5) 0.008(5) -0.006(5) C7 0.048(6) 0.036(7) 0.027(6) 0.019(6) 0.013(5) 0.010(6) C8 0.030(5) 0.035(7) 0.023(5) -0.009(5) 0.000(4) -0.002(5) C9 0.039(6) 0.027(6) 0.017(5) 0.007(5) 0.007(4) 0.007(5) C10 0.034(6) 0.039(7) 0.030(6) 0.013(5) 0.013(5) 0.000(5) C11 0.036(6) 0.031(7) 0.038(7) -0.005(6) 0.009(5) 0.010(5) C12 0.043(6) 0.043(8) 0.033(6) -0.003(6) 0.005(5) -0.011(6) C13 0.067(8) 0.028(8) 0.066(9) -0.005(7) -0.006(7) 0.000(6) C14 0.050(7) 0.040(8) 0.038(7) -0.002(6) 0.011(5) 0.007(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 Br1 C1 1.895(11) . ? Br8 C8 1.874(10) . ? O1 C11 1.348(12) . ? O1 C2 1.380(13) . ? O4 C11 1.190(13) . ? O7 C12 1.387(13) . ? O7 C7 1.408(12) . ? O12 C12 1.150(13) . ? C1 C2 1.386(14) . ? C1 C9 1.394(15) . ? C2 C3 1.384(15) . ? C3 C4 1.333(16) . ? C4 C10 1.414(14) . ? C5 C6 1.346(14) . ? C5 C10 1.409(15) . ? C6 C7 1.422(14) . ? C7 C8 1.338(15) . ? C8 C9 1.443(13) . ? C9 C10 1.438(13) . ? C11 C13 1.500(16) . ? C12 C14 1.491(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 C2 117.7(9) . . ? C12 O7 C7 115.7(9) . . ? C2 C1 C9 120.9(10) . . ? C2 C1 Br1 112.6(9) . . ? C9 C1 Br1 126.4(8) . . ? O1 C2 C3 118.6(10) . . ? O1 C2 C1 119.6(10) . . ? C3 C2 C1 121.7(11) . . ? C4 C3 C2 118.9(11) . . ? C3 C4 C10 122.0(11) . . ? C6 C5 C10 121.9(10) . . ? C5 C6 C7 116.7(11) . . ? C8 C7 O7 121.4(9) . . ? C8 C7 C6 124.5(10) . . ? O7 C7 C6 113.9(10) . . ? C7 C8 C9 120.3(9) . . ? C7 C8 Br8 115.0(7) . . ? C9 C8 Br8 124.7(8) . . ? C1 C9 C10 116.4(9) . . ? C1 C9 C8 128.5(9) . . ? C10 C9 C8 115.0(10) . . ? C5 C10 C4 118.9(10) . . ? C5 C10 C9 121.4(10) . . ? C4 C10 C9 119.5(11) . . ? O4 C11 O1 121.5(11) . . ? O4 C11 C13 127.4(11) . . ? O1 C11 C13 111.0(11) . . ? O12 C12 O7 124.1(11) . . ? O12 C12 C14 129.0(11) . . ? O7 C12 C14 106.9(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 O1 C2 C3 -84.8(12) . . . . ? C11 O1 C2 C1 97.9(11) . . . . ? C9 C1 C2 O1 169.7(9) . . . . ? Br1 C1 C2 O1 -8.0(12) . . . . ? C9 C1 C2 C3 -7.6(16) . . . . ? Br1 C1 C2 C3 174.8(9) . . . . ? O1 C2 C3 C4 -175.7(10) . . . . ? C1 C2 C3 C4 1.6(17) . . . . ? C2 C3 C4 C10 4.8(19) . . . . ? C10 C5 C6 C7 -2.2(16) . . . . ? C12 O7 C7 C8 86.7(12) . . . . ? C12 O7 C7 C6 -98.2(10) . . . . ? C5 C6 C7 C8 1.8(16) . . . . ? C5 C6 C7 O7 -173.1(9) . . . . ? O7 C7 C8 C9 172.2(8) . . . . ? C6 C7 C8 C9 -2.4(16) . . . . ? O7 C7 C8 Br8 -7.8(13) . . . . ? C6 C7 C8 Br8 177.6(8) . . . . ? C2 C1 C9 C10 6.7(14) . . . . ? Br1 C1 C9 C10 -176.0(7) . . . . ? C2 C1 C9 C8 -174.9(10) . . . . ? Br1 C1 C9 C8 2.5(16) . . . . ? C7 C8 C9 C1 -175.4(10) . . . . ? Br8 C8 C9 C1 4.7(15) . . . . ? C7 C8 C9 C10 3.1(14) . . . . ? Br8 C8 C9 C10 -176.9(7) . . . . ? C6 C5 C10 C4 178.9(10) . . . . ? C6 C5 C10 C9 3.3(16) . . . . ? C3 C4 C10 C5 178.9(11) . . . . ? C3 C4 C10 C9 -5.3(17) . . . . ? C1 C9 C10 C5 175.1(10) . . . . ? C8 C9 C10 C5 -3.5(14) . . . . ? C1 C9 C10 C4 -0.5(14) . . . . ? C8 C9 C10 C4 -179.2(9) . . . . ? C2 O1 C11 O4 2.5(14) . . . . ? C2 O1 C11 C13 -175.0(9) . . . . ? C7 O7 C12 O12 4.1(16) . . . . ? C7 O7 C12 C14 -176.5(9) . . . . ? data_t _database_code_CSD 178816 _audit_creation_date 2000-07-10T14:41:03-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C32 H36 O4' _chemical_formula_structural 'C32 H36 O4' _chemical_formula_sum 'C32 H36 O4' _chemical_formula_weight 484.61 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 22.097(2) _cell_length_b 11.505(2) _cell_length_c 34.188(2) _cell_angle_alpha 90 _cell_angle_beta 102.19(2) _cell_angle_gamma 90 _cell_volume 8495.5(17) _cell_formula_units_Z 12 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 1.54178 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.137 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3120 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.581 _exptl_absorpt_correction_T_min 0.8007 _exptl_absorpt_correction_T_max 0.8683 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_number 10030 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_unetI/netI 0.0662 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 65.09 _diffrn_reflns_theta_full 65.09 _diffrn_measured_fraction_theta_full 0.92 _diffrn_measured_fraction_theta_max 0.92 _reflns_number_total 6674 _reflns_number_gt 2842 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0790P)^2^+6.0000P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.00049(5) _refine_ls_number_reflns 6674 _refine_ls_number_parameters 501 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1814 _refine_ls_R_factor_gt 0.0816 _refine_ls_wR_factor_ref 0.2638 _refine_ls_wR_factor_gt 0.2106 _refine_ls_goodness_of_fit_ref 1.269 _refine_ls_restrained_S_all 1.269 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.221 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # 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 0.0181 0.0091 '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 0.0492 0.0322 '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 0.5997(2) 0.4015(4) 0.08877(13) 0.0717(13) Uani 1 1 d . . . C2 C 0.6509(3) 0.3345(5) 0.08851(19) 0.1006(18) Uani 1 1 d . . . C3 C 0.6485(3) 0.2141(6) 0.0864(2) 0.129(3) Uani 1 1 d . . . H3 H 0.6842 0.1707 0.0853 0.155 Uiso 1 1 calc R . . C4 C 0.5942(4) 0.1604(5) 0.08599(17) 0.111(2) Uani 1 1 d . . . H4 H 0.5925 0.0787 0.0852 0.133 Uiso 1 1 calc R . . C4A C 0.5399(3) 0.2231(4) 0.08672(14) 0.0808(14) Uani 1 1 d . . . C5 C 0.4842(3) 0.1628(5) 0.08782(16) 0.0983(19) Uani 1 1 d . . . H5 H 0.4841 0.0811 0.0882 0.118 Uiso 1 1 calc R . . C6 C 0.4315(3) 0.2215(5) 0.08834(18) 0.109(2) Uani 1 1 d . . . H6 H 0.3949 0.1808 0.0891 0.131 Uiso 1 1 calc R . . C7 C 0.4316(3) 0.3408(5) 0.08783(16) 0.0867(15) Uani 1 1 d . . . C8 C 0.4843(2) 0.4057(4) 0.08560(12) 0.0678(12) Uani 1 1 d . . . C8A C 0.5414(2) 0.3451(3) 0.08647(13) 0.0662(12) Uani 1 1 d . . . C9 C 0.61023(18) 0.5284(4) 0.09623(14) 0.0671(12) Uani 1 1 d . . . C10 C 0.60469(18) 0.6101(4) 0.06560(13) 0.0684(12) Uani 1 1 d . . . H10 H 0.5935 0.5839 0.039 0.082 Uiso 1 1 calc R . . C11 C 0.6146(2) 0.7263(4) 0.07223(13) 0.0693(13) Uani 1 1 d . . . C12 C 0.6324(2) 0.7636(4) 0.11143(15) 0.0803(14) Uani 1 1 d . . . C13 C 0.6409(2) 0.6854(4) 0.14299(14) 0.0860(15) Uani 1 1 d . . . H13 H 0.6542 0.7117 0.1694 0.103 Uiso 1 1 calc R . . C14 C 0.6297(2) 0.5686(4) 0.13530(14) 0.0772(13) Uani 1 1 d . . . H14 H 0.6353 0.5156 0.1567 0.093 Uiso 1 1 calc R . . C15 C 0.6037(2) 0.8128(4) 0.03851(14) 0.0923(16) Uani 1 1 d . . . H15A H 0.5681 0.8605 0.0401 0.138 Uiso 1 1 calc R . . H15B H 0.596 0.7718 0.0131 0.138 Uiso 1 1 calc R . . H15C H 0.6399 0.8619 0.0406 0.138 Uiso 1 1 calc R . . C16 C 0.6612(4) 0.9237(5) 0.15608(19) 0.175(4) Uani 1 1 d . . . H16A H 0.6298 0.908 0.1714 0.262 Uiso 1 1 calc R . . H16B H 0.6682 1.0068 0.1553 0.262 Uiso 1 1 calc R . . H16C H 0.6994 0.8851 0.1686 0.262 Uiso 1 1 calc R . . C17 C 0.7498(7) 0.3784(13) 0.0797(4) 0.297(10) Uani 1 1 d . . . H17 H 0.7689 0.3141 0.0973 0.357 Uiso 1 1 calc R . . C18 C 0.7997(5) 0.4678(13) 0.0922(4) 0.350(9) Uani 1 1 d . . . H18A H 0.8276 0.4664 0.0737 0.525 Uiso 1 1 calc R . . H18B H 0.8227 0.4504 0.119 0.525 Uiso 1 1 calc R . . H18C H 0.7811 0.5442 0.0918 0.525 Uiso 1 1 calc R . . C19 C 0.7555(6) 0.3345(12) 0.0454(4) 0.299(7) Uani 1 1 d . . . H19A H 0.7282 0.268 0.0391 0.449 Uiso 1 1 calc R . . H19B H 0.798 0.3101 0.0472 0.449 Uiso 1 1 calc R . . H19C H 0.7446 0.3928 0.0247 0.449 Uiso 1 1 calc R . . C20 C 0.3217(4) 0.3759(9) 0.0747(3) 0.213(5) Uani 1 1 d . . . H20 H 0.3141 0.3102 0.0918 0.256 Uiso 1 1 calc R . . C21 C 0.3014(5) 0.3388(13) 0.0404(3) 0.298(8) Uani 1 1 d . . . H21A H 0.2949 0.4033 0.0217 0.447 Uiso 1 1 calc R . . H21B H 0.2624 0.2991 0.0395 0.447 Uiso 1 1 calc R . . H21C H 0.331 0.285 0.0331 0.447 Uiso 1 1 calc R . . C22 C 0.2831(4) 0.4722(11) 0.0868(4) 0.282(7) Uani 1 1 d . . . H22A H 0.2775 0.5332 0.0668 0.423 Uiso 1 1 calc R . . H22B H 0.3039 0.5037 0.1124 0.423 Uiso 1 1 calc R . . H22C H 0.243 0.4417 0.0889 0.423 Uiso 1 1 calc R . . C23 C 0.47449(17) 0.5329(4) 0.07939(13) 0.0584(11) Uani 1 1 d . . . C24 C 0.47886(19) 0.6123(4) 0.10976(13) 0.0688(12) Uani 1 1 d . . . H24 H 0.4895 0.5856 0.1363 0.083 Uiso 1 1 calc R . . C25 C 0.4684(2) 0.7303(4) 0.10306(14) 0.0728(13) Uani 1 1 d . . . C26 C 0.4513(2) 0.7673(4) 0.06344(14) 0.0730(13) Uani 1 1 d . . . C27 C 0.4453(2) 0.6911(4) 0.03243(14) 0.0758(13) Uani 1 1 d . . . H27 H 0.4333 0.7173 0.0059 0.091 Uiso 1 1 calc R . . C28 C 0.45711(18) 0.5740(4) 0.04049(13) 0.0714(13) Uani 1 1 d . . . H28 H 0.4532 0.5214 0.0191 0.086 Uiso 1 1 calc R . . C29 C 0.4761(3) 0.8141(5) 0.13744(15) 0.114(2) Uani 1 1 d . . . H29A H 0.4906 0.7727 0.1624 0.171 Uiso 1 1 calc R . . H29B H 0.4366 0.8506 0.1378 0.171 Uiso 1 1 calc R . . H29C H 0.506 0.8733 0.1344 0.171 Uiso 1 1 calc R . . C30 C 0.4221(3) 0.9273(5) 0.01879(16) 0.121(2) Uani 1 1 d . . . H30A H 0.4541 0.912 0.0039 0.181 Uiso 1 1 calc R . . H30B H 0.4147 1.0104 0.0192 0.181 Uiso 1 1 calc R . . H30C H 0.3843 0.888 0.006 0.181 Uiso 1 1 calc R . . O2 O 0.7067(2) 0.3929(4) 0.0932(2) 0.174(2) Uani 1 1 d . . . O7 O 0.37994(18) 0.4044(4) 0.09037(14) 0.1241(15) Uani 1 1 d . . . O12 O 0.64078(19) 0.8810(3) 0.11616(11) 0.1123(13) Uani 1 1 d . . . O26 O 0.44179(17) 0.8858(3) 0.05869(10) 0.1010(12) Uani 1 1 d . . . C31 C 0.9425(2) 1.1618(4) 0.24850(13) 0.0738(13) Uani 1 1 d . . . C32 C 0.8897(3) 1.2261(6) 0.24982(17) 0.1002(18) Uani 1 1 d . . . C33 C 0.8919(4) 1.3463(7) 0.2510(2) 0.126(2) Uani 1 1 d . . . H33 H 0.8558 1.3883 0.2519 0.151 Uiso 1 1 calc R . . C34 C 0.9450(4) 1.4046(5) 0.25099(18) 0.120(2) Uani 1 1 d . . . H34 H 0.9454 1.4863 0.2516 0.144 Uiso 1 1 calc R . . C34A C 1 1.3423(6) 0.25 0.092(2) Uani 1 2 d S . . C38A C 1 1.2213(6) 0.25 0.0724(18) Uani 1 2 d S . . C39 C 0.93154(19) 1.0357(4) 0.24224(14) 0.0681(12) Uani 1 1 d . . . C40 C 0.9378(2) 0.9556(4) 0.27315(14) 0.0754(13) Uani 1 1 d . . . H40 H 0.9495 0.9828 0.2996 0.09 Uiso 1 1 calc R . . C41 C 0.9277(2) 0.8370(4) 0.26708(14) 0.0799(14) Uani 1 1 d . . . C42 C 0.9089(2) 0.8008(4) 0.22794(15) 0.0833(15) Uani 1 1 d . . . C43 C 0.9012(2) 0.8756(5) 0.19645(15) 0.0888(15) Uani 1 1 d . . . H43 H 0.8884 0.8479 0.1701 0.107 Uiso 1 1 calc R . . C44 C 0.9124(2) 0.9930(4) 0.20359(14) 0.0791(14) Uani 1 1 d . . . H44 H 0.907 1.0448 0.1819 0.095 Uiso 1 1 calc R . . C45 C 0.9386(3) 0.7528(5) 0.30197(15) 0.113(2) Uani 1 1 d . . . H45A H 0.9099 0.6882 0.2959 0.17 Uiso 1 1 calc R . . H45B H 0.932 0.7923 0.3258 0.17 Uiso 1 1 calc R . . H45C H 0.9807 0.7239 0.3066 0.17 Uiso 1 1 calc R . . C46 C 0.8781(4) 0.6391(5) 0.18410(19) 0.166(3) Uani 1 1 d . . . H46A H 0.8415 0.6825 0.1715 0.249 Uiso 1 1 calc R . . H46B H 0.8676 0.5575 0.1852 0.249 Uiso 1 1 calc R . . H46C H 0.9098 0.6482 0.1686 0.249 Uiso 1 1 calc R . . C47 C 0.7775(4) 1.2019(9) 0.2359(3) 0.170(4) Uani 1 1 d . . . H47 H 0.7713 1.2715 0.2516 0.204 Uiso 1 1 calc R . . C48 C 0.7624(5) 1.2351(12) 0.1954(3) 0.308(8) Uani 1 1 d . . . H48A H 0.7776 1.3131 0.1926 0.462 Uiso 1 1 calc R . . H48B H 0.7178 1.2335 0.186 0.462 Uiso 1 1 calc R . . H48C H 0.7815 1.1816 0.1797 0.462 Uiso 1 1 calc R . . C49 C 0.7361(3) 1.1062(9) 0.2474(3) 0.202(4) Uani 1 1 d . . . H49A H 0.7543 1.0308 0.2445 0.302 Uiso 1 1 calc R . . H49B H 0.6954 1.1105 0.2301 0.302 Uiso 1 1 calc R . . H49C H 0.7326 1.1168 0.275 0.302 Uiso 1 1 calc R . . O32 O 0.8374(2) 1.1636(4) 0.25109(15) 0.1397(17) Uani 1 1 d . . . O42 O 0.9004(2) 0.6815(3) 0.22349(11) 0.1221(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.069(3) 0.060(3) 0.083(3) -0.004(2) 0.008(2) 0.002(3) C2 0.072(4) 0.074(4) 0.153(6) -0.019(3) 0.019(3) 0.011(3) C3 0.110(5) 0.084(5) 0.181(7) -0.023(4) 0.003(5) 0.031(4) C4 0.146(6) 0.049(3) 0.120(5) -0.011(3) -0.011(4) 0.016(4) C4A 0.112(4) 0.049(3) 0.073(3) -0.001(2) 0.001(3) 0.001(3) C5 0.133(5) 0.055(3) 0.098(4) 0.002(3) 0.005(4) -0.025(4) C6 0.122(5) 0.080(4) 0.125(5) -0.007(4) 0.024(4) -0.042(4) C7 0.082(4) 0.074(4) 0.102(4) -0.008(3) 0.013(3) -0.020(3) C8 0.076(3) 0.057(3) 0.067(3) -0.005(2) 0.005(2) -0.015(2) C8A 0.076(3) 0.053(3) 0.065(3) 0.001(2) 0.003(2) 0.000(3) C9 0.053(2) 0.057(3) 0.087(3) 0.001(3) 0.005(2) -0.003(2) C10 0.069(3) 0.070(3) 0.062(3) -0.006(2) 0.004(2) -0.006(2) C11 0.071(3) 0.067(3) 0.065(3) 0.002(2) 0.005(2) -0.011(2) C12 0.093(4) 0.061(3) 0.079(3) -0.002(3) 0.000(3) -0.020(3) C13 0.104(4) 0.070(3) 0.073(3) -0.004(3) -0.007(3) -0.018(3) C14 0.082(3) 0.069(3) 0.076(3) 0.007(3) 0.006(3) -0.006(3) C15 0.107(4) 0.087(4) 0.079(3) 0.014(3) 0.009(3) -0.013(3) C16 0.291(10) 0.091(5) 0.115(5) -0.027(4) -0.020(6) -0.057(5) C17 0.308(17) 0.321(16) 0.346(18) -0.227(14) 0.257(15) -0.179(14) C18 0.222(11) 0.43(2) 0.420(19) -0.220(17) 0.126(12) -0.201(13) C19 0.257(14) 0.312(18) 0.37(2) -0.082(15) 0.152(14) -0.066(12) C20 0.144(8) 0.194(9) 0.243(12) -0.090(8) -0.089(7) 0.052(7) C21 0.160(9) 0.50(2) 0.208(11) -0.148(13) -0.029(8) 0.039(11) C22 0.134(7) 0.276(14) 0.394(17) -0.141(12) -0.037(8) 0.060(8) C23 0.052(2) 0.058(3) 0.064(3) 0.001(2) 0.010(2) 0.000(2) C24 0.075(3) 0.070(3) 0.058(3) 0.003(2) 0.009(2) 0.007(2) C25 0.080(3) 0.068(3) 0.068(3) -0.004(2) 0.011(2) 0.014(2) C26 0.082(3) 0.068(3) 0.063(3) 0.005(3) 0.002(2) 0.006(3) C27 0.077(3) 0.079(3) 0.064(3) 0.008(3) -0.002(2) -0.003(3) C28 0.071(3) 0.067(3) 0.071(3) -0.007(2) 0.002(2) -0.007(2) C29 0.165(6) 0.091(4) 0.083(4) -0.015(3) 0.015(4) 0.018(4) C30 0.167(6) 0.086(4) 0.096(4) 0.032(3) -0.002(4) 0.014(4) O2 0.077(3) 0.138(4) 0.316(8) -0.071(5) 0.060(4) 0.009(3) O7 0.073(2) 0.123(3) 0.178(4) -0.030(3) 0.031(3) -0.024(2) O12 0.165(3) 0.065(2) 0.095(3) -0.0059(19) 0.000(2) -0.034(2) O26 0.142(3) 0.064(2) 0.090(2) 0.0114(19) 0.007(2) 0.017(2) C31 0.084(3) 0.072(3) 0.064(3) 0.003(3) 0.014(3) 0.009(3) C32 0.103(5) 0.097(5) 0.096(4) 0.001(3) 0.011(4) 0.022(4) C33 0.135(6) 0.113(6) 0.125(6) 0.002(4) 0.017(5) 0.055(5) C34 0.177(7) 0.063(4) 0.105(5) 0.000(3) -0.005(5) 0.025(4) C34A 0.134(7) 0.061(5) 0.070(5) 0 -0.006(5) 0 C38A 0.099(5) 0.058(4) 0.059(4) 0 0.013(4) 0 C39 0.063(3) 0.074(3) 0.068(3) -0.001(3) 0.014(2) -0.001(2) C40 0.073(3) 0.087(3) 0.066(3) -0.001(3) 0.015(2) -0.007(3) C41 0.085(3) 0.086(4) 0.066(3) 0.006(3) 0.009(3) -0.015(3) C42 0.106(4) 0.067(3) 0.073(3) 0.007(3) 0.009(3) -0.015(3) C43 0.104(4) 0.090(4) 0.067(3) -0.007(3) 0.006(3) -0.007(3) C44 0.082(3) 0.088(4) 0.065(3) 0.006(3) 0.011(2) 0.005(3) C45 0.138(5) 0.108(4) 0.086(4) 0.023(3) 0.004(3) -0.026(4) C46 0.268(9) 0.100(5) 0.104(5) -0.014(4) -0.021(5) -0.035(5) C47 0.109(6) 0.199(9) 0.165(8) -0.008(6) -0.051(5) 0.005(6) C48 0.284(14) 0.375(18) 0.195(10) 0.101(11) -0.107(10) -0.080(12) C49 0.092(5) 0.250(11) 0.248(11) 0.007(9) 0.004(6) -0.020(6) O32 0.078(3) 0.168(4) 0.176(4) 0.014(3) 0.035(3) 0.030(3) O42 0.182(4) 0.085(3) 0.085(3) -0.001(2) -0.003(2) -0.035(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 C1 C2 1.370(6) . ? C1 C8A 1.430(6) . ? C1 C9 1.491(6) . ? C2 O2 1.383(6) . ? C2 C3 1.388(7) . ? C3 C4 1.348(8) . ? C4 C4A 1.404(7) . ? C4A C8A 1.404(6) . ? C4A C5 1.420(7) . ? C5 C6 1.350(7) . ? C6 C7 1.373(7) . ? C7 O7 1.374(6) . ? C7 C8 1.399(6) . ? C8 C8A 1.437(6) . ? C8 C23 1.488(6) . ? C9 C14 1.393(6) . ? C9 C10 1.393(6) . ? C10 C11 1.366(6) . ? C11 C12 1.383(6) . ? C11 C15 1.504(6) . ? C12 O12 1.368(5) . ? C12 C13 1.387(6) . ? C13 C14 1.382(6) . ? C16 O12 1.431(6) . ? C17 O2 1.156(10) . ? C17 C19 1.305(14) . ? C17 C18 1.502(13) . ? C20 C21 1.240(10) . ? C20 O7 1.326(8) . ? C20 C22 1.509(11) . ? C23 C24 1.371(6) . ? C23 C28 1.387(5) . ? C24 C25 1.388(6) . ? C25 C26 1.394(6) . ? C25 C29 1.502(6) . ? C26 C27 1.360(6) . ? C26 O26 1.384(5) . ? C27 C28 1.389(6) . ? C30 O26 1.424(5) . ? C31 C32 1.390(7) . ? C31 C38A 1.435(5) . ? C31 C39 1.478(6) . ? C32 O32 1.371(7) . ? C32 C33 1.384(8) . ? C33 C34 1.350(8) . ? C34 C34A 1.418(7) . ? C34A C38A 1.392(9) . ? C34A C34 1.418(7) 2_755 ? C38A C31 1.435(5) 2_755 ? C39 C40 1.387(6) . ? C39 C44 1.389(6) . ? C40 C41 1.390(6) . ? C41 C42 1.379(6) . ? C41 C45 1.516(6) . ? C42 C43 1.361(6) . ? C42 O42 1.388(5) . ? C43 C44 1.386(6) . ? C46 O42 1.420(6) . ? C47 O32 1.387(7) . ? C47 C48 1.407(11) . ? C47 C49 1.533(11) . ? 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 C8A 118.7(5) . . ? C2 C1 C9 116.9(4) . . ? C8A C1 C9 124.0(4) . . ? C1 C2 O2 116.3(5) . . ? C1 C2 C3 122.7(6) . . ? O2 C2 C3 120.9(5) . . ? C4 C3 C2 118.8(6) . . ? C3 C4 C4A 121.8(5) . . ? C4 C4A C8A 119.5(5) . . ? C4 C4A C5 119.8(5) . . ? C8A C4A C5 120.6(5) . . ? C6 C5 C4A 120.8(5) . . ? C5 C6 C7 119.7(6) . . ? C6 C7 O7 121.9(5) . . ? C6 C7 C8 122.5(6) . . ? O7 C7 C8 115.5(5) . . ? C7 C8 C8A 118.6(5) . . ? C7 C8 C23 115.8(4) . . ? C8A C8 C23 125.5(4) . . ? C4A C8A C1 118.4(5) . . ? C4A C8A C8 117.6(5) . . ? C1 C8A C8 124.0(4) . . ? C14 C9 C10 117.2(4) . . ? C14 C9 C1 119.6(4) . . ? C10 C9 C1 123.1(4) . . ? C11 C10 C9 123.4(4) . . ? C10 C11 C12 117.9(4) . . ? C10 C11 C15 121.8(4) . . ? C12 C11 C15 120.3(4) . . ? O12 C12 C11 115.1(4) . . ? O12 C12 C13 123.8(4) . . ? C11 C12 C13 121.1(4) . . ? C14 C13 C12 119.6(4) . . ? C13 C14 C9 120.8(4) . . ? O2 C17 C19 131.1(16) . . ? O2 C17 C18 114.0(10) . . ? C19 C17 C18 108.4(10) . . ? C21 C20 O7 126.4(12) . . ? C21 C20 C22 113.5(9) . . ? O7 C20 C22 105.3(7) . . ? C24 C23 C28 117.4(4) . . ? C24 C23 C8 124.2(4) . . ? C28 C23 C8 118.4(4) . . ? C23 C24 C25 123.0(4) . . ? C24 C25 C26 117.4(4) . . ? C24 C25 C29 120.7(4) . . ? C26 C25 C29 121.8(4) . . ? C27 C26 O26 123.8(4) . . ? C27 C26 C25 121.5(4) . . ? O26 C26 C25 114.7(4) . . ? C26 C27 C28 119.2(4) . . ? C23 C28 C27 121.6(4) . . ? C17 O2 C2 132.4(8) . . ? C20 O7 C7 126.2(6) . . ? C12 O12 C16 117.3(4) . . ? C26 O26 C30 116.8(4) . . ? C32 C31 C38A 119.1(5) . . ? C32 C31 C39 114.5(5) . . ? C38A C31 C39 126.2(5) . . ? O32 C32 C33 123.2(6) . . ? O32 C32 C31 116.1(6) . . ? C33 C32 C31 120.6(6) . . ? C34 C33 C32 121.4(6) . . ? C33 C34 C34A 119.8(6) . . ? C38A C34A C34 120.4(4) . 2_755 ? C38A C34A C34 120.4(4) . . ? C34 C34A C34 119.3(9) 2_755 . ? C34A C38A C31 118.5(3) . 2_755 ? C34A C38A C31 118.5(3) . . ? C31 C38A C31 122.9(6) 2_755 . ? C40 C39 C44 116.8(4) . . ? C40 C39 C31 123.7(4) . . ? C44 C39 C31 119.5(4) . . ? C39 C40 C41 123.4(5) . . ? C42 C41 C40 116.6(5) . . ? C42 C41 C45 122.3(5) . . ? C40 C41 C45 121.1(5) . . ? C43 C42 C41 122.5(5) . . ? C43 C42 O42 123.1(5) . . ? C41 C42 O42 114.3(4) . . ? C42 C43 C44 119.3(5) . . ? C43 C44 C39 121.3(5) . . ? O32 C47 C48 117.6(10) . . ? O32 C47 C49 104.4(7) . . ? C48 C47 C49 114.7(8) . . ? C32 O32 C47 124.5(6) . . ? C42 O42 C46 117.1(4) . . ? data_new _database_code_CSD 178817 _audit_creation_date 2000-12-15T11:53:24-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C38 H38 O4' _chemical_formula_structural 'C38 H38 O4' _chemical_formula_sum 'C38 H48 O4' _chemical_formula_weight 568.76 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M ' P na21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 16.808(2) _cell_length_b 22.023(2) _cell_length_c 9.000(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3331.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.3 _cell_measurement_theta_max 14.5 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_factor_muR 0.004 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; ? ; _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_correction_T_ave 0.8431 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _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 0.2817E-2 _diffrn_orient_matrix_ub_12 0.48855E-1 _diffrn_orient_matrix_ub_13 0.26316E-1 _diffrn_orient_matrix_ub_21 -0.4548E-2 _diffrn_orient_matrix_ub_22 -0.34415E-1 _diffrn_orient_matrix_ub_23 0.37283E-1 _diffrn_orient_matrix_ub_31 0.111598 _diffrn_orient_matrix_ub_32 -0.2947E-2 _diffrn_orient_matrix_ub_33 0.1295E-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 0 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_standards_decay_corr_max 1 _diffrn_standards_decay_corr_min 1 _diffrn_reflns_number 6087 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_unetI/netI 0.0821 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 24.94 _diffrn_reflns_theta_full 24.94 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 3107 _reflns_number_gt 1972 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (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, 1999)' #----------------------------------------------------------------------------# # 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3107 _refine_ls_number_parameters 515 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.096 _refine_ls_R_factor_gt 0.049 _refine_ls_wR_factor_ref 0.1009 _refine_ls_wR_factor_gt 0.085 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.002 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_diff_density_max 0.205 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # 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 C1 C 0.5561(3) 0.3931(2) 0.2057(5) 0.0350(11) Uani 1 1 d . . . C2 C 0.4996(3) 0.3832(2) 0.0949(5) 0.0409(11) Uani 1 1 d . . . C3 C 0.4903(3) 0.4232(2) -0.0257(6) 0.0470(13) Uani 1 1 d . . . C4 C 0.5334(3) 0.4752(2) -0.0300(6) 0.0449(12) Uani 1 1 d . . . C4A C 0.5903(3) 0.4888(2) 0.0807(5) 0.0398(11) Uani 1 1 d . . . C5 C 0.6296(3) 0.5447(2) 0.0767(6) 0.0434(12) Uani 1 1 d . . . C6 C 0.6877(3) 0.5581(2) 0.1743(5) 0.0446(12) Uani 1 1 d . . . C7 C 0.7119(3) 0.5138(2) 0.2782(5) 0.0389(11) Uani 1 1 d . . . C8 C 0.6743(3) 0.45802(18) 0.2907(5) 0.0338(11) Uani 1 1 d . . . C8A C 0.6071(2) 0.44543(19) 0.1952(5) 0.0336(10) Uani 1 1 d . . . C9 C 0.5563(2) 0.35074(19) 0.3362(5) 0.0340(11) Uani 1 1 d . . . C10 C 0.5607(3) 0.2885(2) 0.3169(5) 0.0379(11) Uani 1 1 d . . . C11 C 0.5641(3) 0.2464(2) 0.4325(5) 0.0380(12) Uani 1 1 d . . . C12 C 0.5622(3) 0.2710(2) 0.5780(5) 0.0382(11) Uani 1 1 d . . . C13 C 0.5542(3) 0.3325(2) 0.6003(5) 0.0399(12) Uani 1 1 d . . . C14 C 0.5518(3) 0.3722(2) 0.4807(5) 0.0369(11) Uani 1 1 d . . . C15 C 0.5721(3) 0.1780(2) 0.4038(5) 0.0455(13) Uani 1 1 d . . . C16 C 0.5686(5) 0.1639(3) 0.2368(6) 0.0664(18) Uani 1 1 d . . . C17 C 0.5034(4) 0.1433(3) 0.4760(8) 0.0668(17) Uani 1 1 d . . . C18 C 0.6525(4) 0.1559(3) 0.4623(8) 0.0583(15) Uani 1 1 d . . . C19 C 0.5661(6) 0.2535(3) 0.8402(6) 0.083(2) Uani 1 1 d . . . C20 C 0.3707(3) 0.3362(3) 0.0682(6) 0.0597(15) Uani 1 1 d . . . H20 H 0.3655 0.3505 -0.0357 0.072 Uiso 1 1 calc R . . C21 C 0.3403(4) 0.2724(3) 0.0769(7) 0.0785(19) Uani 1 1 d . . . H21A H 0.3697 0.2471 0.0079 0.118 Uiso 1 1 calc R . . H21B H 0.2843 0.2717 0.0513 0.118 Uiso 1 1 calc R . . H21C H 0.3473 0.2571 0.1771 0.118 Uiso 1 1 calc R . . C22 C 0.3282(4) 0.3797(3) 0.1665(9) 0.116(3) Uani 1 1 d . . . H22A H 0.3499 0.4201 0.1526 0.174 Uiso 1 1 calc R . . H22B H 0.3349 0.3675 0.2693 0.174 Uiso 1 1 calc R . . H22C H 0.272 0.3799 0.1418 0.174 Uiso 1 1 calc R . . C23 C 0.8488(3) 0.5389(3) 0.3023(7) 0.0661(16) Uani 1 1 d . . . H23 H 0.8419 0.566 0.2156 0.079 Uiso 1 1 calc R . . C24 C 0.8983(4) 0.5700(4) 0.4166(9) 0.163(4) Uani 1 1 d . . . H24A H 0.8732 0.608 0.4445 0.244 Uiso 1 1 calc R . . H24B H 0.9507 0.5781 0.3763 0.244 Uiso 1 1 calc R . . H24C H 0.9031 0.5442 0.5035 0.244 Uiso 1 1 calc R . . C25 C 0.8863(3) 0.4827(3) 0.2546(8) 0.099(2) Uani 1 1 d . . . H25A H 0.8531 0.463 0.1809 0.149 Uiso 1 1 calc R . . H25B H 0.893 0.456 0.3394 0.149 Uiso 1 1 calc R . . H25C H 0.9379 0.4916 0.2116 0.149 Uiso 1 1 calc R . . C26 C 0.7113(2) 0.4127(2) 0.3928(5) 0.0337(11) Uani 1 1 d . . . C27 C 0.7296(3) 0.4289(2) 0.5411(5) 0.0365(11) Uani 1 1 d . . . C28 C 0.7687(3) 0.3908(2) 0.6381(5) 0.0378(11) Uani 1 1 d . . . C29 C 0.7880(2) 0.3327(2) 0.5873(5) 0.0383(11) Uani 1 1 d . . . C30 C 0.7710(3) 0.3155(2) 0.4411(5) 0.0411(12) Uani 1 1 d . . . C31 C 0.7338(3) 0.3562(2) 0.3448(5) 0.0335(11) Uani 1 1 d . . . C32 C 0.7903(3) 0.4125(2) 0.7962(5) 0.0469(13) Uani 1 1 d . . . C33 C 0.7679(4) 0.4791(3) 0.8193(6) 0.0542(14) Uani 1 1 d . . . C34 C 0.8796(4) 0.4057(3) 0.8217(7) 0.0629(16) Uani 1 1 d . . . C35 C 0.7455(4) 0.3750(3) 0.9122(6) 0.0601(16) Uani 1 1 d . . . C36 C 0.8476(4) 0.2357(3) 0.6326(7) 0.0636(18) Uani 1 1 d . . . O1 O 0.5668(2) 0.23026(14) 0.6927(4) 0.0558(10) Uani 1 1 d . . . O2 O 0.45309(18) 0.33209(14) 0.1035(4) 0.0527(9) Uani 1 1 d . . . O3 O 0.77335(19) 0.52881(14) 0.3712(3) 0.0460(8) Uani 1 1 d . . . O4 O 0.8245(2) 0.29358(15) 0.6834(3) 0.0546(9) Uani 1 1 d . . . H3 H 0.446(3) 0.414(2) -0.101(6) 0.064(15) Uiso 1 1 d . . . H4 H 0.526(2) 0.5070(19) -0.116(6) 0.052(13) Uiso 1 1 d . . . H5 H 0.618(2) 0.5781(18) 0.009(5) 0.045(13) Uiso 1 1 d . . . H6 H 0.716(3) 0.596(2) 0.176(5) 0.049(14) Uiso 1 1 d . . . H10 H 0.564(2) 0.2714(17) 0.220(5) 0.029(11) Uiso 1 1 d . . . H13 H 0.557(3) 0.3528(19) 0.694(6) 0.053(14) Uiso 1 1 d . . . H14 H 0.549(2) 0.4147(16) 0.502(4) 0.019(10) Uiso 1 1 d . . . H16A H 0.571(3) 0.116(2) 0.220(7) 0.084(18) Uiso 1 1 d . . . H16B H 0.620(3) 0.186(2) 0.191(6) 0.074(17) Uiso 1 1 d . . . H16C H 0.507(3) 0.177(2) 0.196(6) 0.070(16) Uiso 1 1 d . . . H17A H 0.442(5) 0.161(3) 0.445(11) 0.18(4) Uiso 1 1 d . . . H17B H 0.511(3) 0.100(2) 0.468(6) 0.063(16) Uiso 1 1 d . . . H17C H 0.499(3) 0.155(2) 0.574(6) 0.067(19) Uiso 1 1 d . . . H18A H 0.655(2) 0.106(2) 0.436(5) 0.054(13) Uiso 1 1 d . . . H18B H 0.660(3) 0.159(2) 0.565(7) 0.08(2) Uiso 1 1 d . . . H18C H 0.705(3) 0.179(2) 0.405(6) 0.080(17) Uiso 1 1 d . . . H19A H 0.510(3) 0.273(3) 0.859(7) 0.09(2) Uiso 1 1 d . . . H19B H 0.567(3) 0.218(2) 0.897(7) 0.081(19) Uiso 1 1 d . . . H19C H 0.616(3) 0.281(3) 0.859(8) 0.12(3) Uiso 1 1 d . . . H27 H 0.715(2) 0.4704(18) 0.569(4) 0.025(10) Uiso 1 1 d . . . H30 H 0.788(2) 0.2739(18) 0.397(5) 0.040(12) Uiso 1 1 d . . . H31 H 0.723(2) 0.3402(16) 0.241(5) 0.028(11) Uiso 1 1 d . . . H33A H 0.805(3) 0.505(2) 0.751(6) 0.069(17) Uiso 1 1 d . . . H33B H 0.707(3) 0.486(2) 0.793(6) 0.064(16) Uiso 1 1 d . . . H33C H 0.786(3) 0.492(3) 0.916(7) 0.09(2) Uiso 1 1 d . . . H34A H 0.908(3) 0.430(2) 0.740(6) 0.054(15) Uiso 1 1 d . . . H34B H 0.901(3) 0.360(2) 0.813(6) 0.073(17) Uiso 1 1 d . . . H34C H 0.893(3) 0.424(2) 0.910(5) 0.046(14) Uiso 1 1 d . . . H35A H 0.751(3) 0.329(2) 0.890(5) 0.049(14) Uiso 1 1 d . . . H35B H 0.764(3) 0.396(2) 1.019(6) 0.076(17) Uiso 1 1 d . . . H35C H 0.688(3) 0.378(2) 0.894(6) 0.061(16) Uiso 1 1 d . . . H36A H 0.872(3) 0.213(2) 0.711(7) 0.074(17) Uiso 1 1 d . . . H36B H 0.797(3) 0.212(2) 0.603(7) 0.10(2) Uiso 1 1 d . . . H36C H 0.897(4) 0.244(3) 0.548(8) 0.12(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 C1 0.041(3) 0.044(3) 0.020(2) 0.000(2) 0.007(2) 0.007(2) C2 0.050(3) 0.042(3) 0.031(3) 0.004(2) 0.000(2) 0.002(2) C3 0.048(3) 0.057(3) 0.035(3) 0.005(3) -0.005(3) 0.013(3) C4 0.053(3) 0.050(3) 0.032(3) 0.015(3) 0.002(3) 0.011(3) C4A 0.048(3) 0.042(3) 0.030(2) 0.008(2) 0.011(2) 0.010(2) C5 0.051(3) 0.041(3) 0.039(3) 0.015(3) 0.011(3) 0.011(2) C6 0.055(3) 0.045(3) 0.034(3) 0.006(3) 0.005(3) 0.005(3) C7 0.042(3) 0.042(3) 0.032(2) -0.002(2) 0.005(2) -0.004(2) C8 0.041(3) 0.037(3) 0.023(2) 0.003(2) 0.008(2) 0.005(2) C8A 0.040(3) 0.036(3) 0.025(2) 0.005(2) 0.004(2) 0.008(2) C9 0.037(3) 0.035(3) 0.030(2) 0.005(2) -0.003(2) -0.002(2) C10 0.048(3) 0.040(3) 0.025(3) -0.003(2) 0.002(2) 0.002(2) C11 0.045(3) 0.040(3) 0.029(3) 0.005(2) 0.003(2) 0.001(2) C12 0.051(3) 0.038(3) 0.025(2) 0.006(2) 0.004(2) -0.003(2) C13 0.051(3) 0.044(3) 0.026(3) 0.001(3) 0.003(2) -0.001(2) C14 0.041(3) 0.038(3) 0.031(3) 0.001(2) 0.004(2) 0.002(2) C15 0.063(3) 0.042(3) 0.031(3) 0.002(2) 0.001(2) -0.002(3) C16 0.103(6) 0.045(4) 0.051(4) -0.010(3) 0.007(4) 0.001(4) C17 0.087(5) 0.050(4) 0.063(4) 0.003(4) 0.016(4) -0.016(4) C18 0.068(4) 0.049(4) 0.059(4) 0.009(3) -0.002(3) 0.014(3) C19 0.155(8) 0.066(4) 0.029(3) 0.010(3) -0.002(4) -0.003(6) C20 0.052(3) 0.075(4) 0.052(3) 0.000(3) -0.004(3) -0.010(3) C21 0.082(4) 0.088(5) 0.065(4) -0.002(4) -0.006(4) -0.036(4) C22 0.080(5) 0.115(6) 0.153(8) -0.053(6) 0.046(5) -0.012(5) C23 0.063(4) 0.089(5) 0.046(3) 0.002(3) 0.000(3) -0.011(3) C24 0.080(5) 0.269(11) 0.138(8) -0.122(8) 0.034(5) -0.090(6) C25 0.055(4) 0.120(6) 0.123(6) -0.040(5) 0.005(4) 0.009(4) C26 0.032(2) 0.044(3) 0.025(2) 0.006(2) 0.004(2) -0.001(2) C27 0.040(3) 0.038(3) 0.032(3) 0.001(2) 0.006(2) 0.006(2) C28 0.041(3) 0.047(3) 0.025(2) 0.002(2) 0.004(2) 0.002(2) C29 0.038(3) 0.045(3) 0.031(3) 0.006(2) -0.001(2) 0.007(2) C30 0.044(3) 0.042(3) 0.038(3) 0.000(2) 0.004(2) 0.002(3) C31 0.041(3) 0.037(3) 0.023(3) 0.001(2) 0.002(2) 0.001(2) C32 0.051(3) 0.064(4) 0.026(2) -0.001(2) -0.007(2) 0.004(3) C33 0.076(4) 0.056(4) 0.030(3) -0.007(3) -0.001(3) 0.006(3) C34 0.059(4) 0.092(5) 0.037(3) -0.018(4) -0.012(3) 0.005(4) C35 0.067(4) 0.081(5) 0.033(3) -0.001(3) 0.004(3) 0.001(4) C36 0.078(5) 0.051(4) 0.061(4) 0.015(3) -0.019(4) 0.023(3) O1 0.094(3) 0.047(2) 0.0265(18) 0.0073(16) 0.006(2) -0.0025(19) O2 0.051(2) 0.053(2) 0.055(2) 0.0089(18) -0.0123(19) -0.0033(18) O3 0.051(2) 0.054(2) 0.0326(17) 0.0022(16) 0.0038(17) -0.0071(17) O4 0.070(2) 0.058(2) 0.036(2) 0.0062(18) -0.0102(18) 0.0203(19) #----------------------------------------------------------------------------# # 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 1.395(6) . ? C1 C8A 1.439(6) . ? C1 C9 1.500(6) . ? C2 O2 1.372(5) . ? C2 C3 1.406(6) . ? C3 C4 1.355(6) . ? C4 C4A 1.414(7) . ? C4A C5 1.396(6) . ? C4A C8A 1.434(6) . ? C5 C6 1.347(7) . ? C6 C7 1.411(6) . ? C7 O3 1.369(5) . ? C7 C8 1.386(6) . ? C8 C8A 1.447(6) . ? C8 C26 1.492(6) . ? C9 C10 1.383(6) . ? C9 C14 1.385(6) . ? C10 C11 1.395(6) . ? C11 C12 1.418(6) . ? C11 C15 1.533(6) . ? C12 O1 1.370(5) . ? C12 C13 1.376(6) . ? C13 C14 1.386(6) . ? C15 C18 1.529(8) . ? C15 C17 1.532(7) . ? C15 C16 1.536(7) . ? C19 O1 1.423(7) . ? C20 O2 1.424(5) . ? C20 C22 1.486(7) . ? C20 C21 1.497(7) . ? C23 O3 1.428(6) . ? C23 C25 1.453(7) . ? C23 C24 1.491(8) . ? C26 C31 1.372(6) . ? C26 C27 1.415(6) . ? C27 C28 1.379(6) . ? C28 C29 1.397(6) . ? C28 C32 1.545(6) . ? C29 O4 1.367(5) . ? C29 C30 1.398(7) . ? C30 C31 1.394(6) . ? C32 C34 1.526(7) . ? C32 C33 1.527(7) . ? C32 C35 1.531(7) . ? C36 O4 1.409(7) . ? 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 C8A 119.0(4) . . ? C2 C1 C9 117.6(4) . . ? C8A C1 C9 123.3(4) . . ? O2 C2 C1 118.4(4) . . ? O2 C2 C3 119.6(4) . . ? C1 C2 C3 121.9(4) . . ? C4 C3 C2 119.5(5) . . ? C3 C4 C4A 121.4(5) . . ? C5 C4A C4 119.3(4) . . ? C5 C4A C8A 120.8(4) . . ? C4 C4A C8A 119.9(4) . . ? C6 C5 C4A 121.3(5) . . ? C5 C6 C7 119.3(5) . . ? O3 C7 C8 120.5(4) . . ? O3 C7 C6 117.1(4) . . ? C8 C7 C6 122.3(4) . . ? C7 C8 C8A 118.5(4) . . ? C7 C8 C26 116.9(4) . . ? C8A C8 C26 124.3(4) . . ? C4A C8A C1 117.6(4) . . ? C4A C8A C8 117.0(4) . . ? C1 C8A C8 125.4(4) . . ? C10 C9 C14 117.3(4) . . ? C10 C9 C1 121.2(4) . . ? C14 C9 C1 121.5(4) . . ? C9 C10 C11 124.5(4) . . ? C10 C11 C12 115.7(4) . . ? C10 C11 C15 122.1(4) . . ? C12 C11 C15 122.2(4) . . ? O1 C12 C13 122.7(4) . . ? O1 C12 C11 116.4(4) . . ? C13 C12 C11 120.9(4) . . ? C12 C13 C14 120.6(5) . . ? C9 C14 C13 120.8(4) . . ? C18 C15 C17 111.1(5) . . ? C18 C15 C11 109.5(4) . . ? C17 C15 C11 110.7(5) . . ? C18 C15 C16 107.8(5) . . ? C17 C15 C16 106.5(5) . . ? C11 C15 C16 111.1(4) . . ? O2 C20 C22 112.1(5) . . ? O2 C20 C21 105.0(5) . . ? C22 C20 C21 114.2(5) . . ? O3 C23 C25 112.4(5) . . ? O3 C23 C24 105.5(5) . . ? C25 C23 C24 110.7(6) . . ? C31 C26 C27 117.8(4) . . ? C31 C26 C8 121.9(4) . . ? C27 C26 C8 120.2(4) . . ? C28 C27 C26 123.1(4) . . ? C27 C28 C29 117.5(4) . . ? C27 C28 C32 120.4(4) . . ? C29 C28 C32 122.1(4) . . ? O4 C29 C28 118.3(4) . . ? O4 C29 C30 121.1(4) . . ? C28 C29 C30 120.6(4) . . ? C31 C30 C29 120.2(5) . . ? C26 C31 C30 120.7(4) . . ? C34 C32 C33 108.5(5) . . ? C34 C32 C35 109.2(5) . . ? C33 C32 C35 107.6(5) . . ? C34 C32 C28 109.9(4) . . ? C33 C32 C28 111.4(4) . . ? C35 C32 C28 110.2(4) . . ? C12 O1 C19 117.8(4) . . ? C2 O2 C20 119.3(4) . . ? C7 O3 C23 116.2(4) . . ? C29 O4 C36 119.2(4) . . ?