# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Janet Scott' _publ_contact_author_email JANET.L.SCOTT@UNILEVER.COM _publ_section_title ; Platform Technology for Dienone and Phenol-Formaldehyde Architectures ; loop_ _publ_author_name 'Janet Scott' 'Marilena A. Giarrusso' 'Luke T Higham' 'Ulf Kreher' 'Ram Mohan' 'Anthony Rosamilia' ; C.R.Strauss ; data_21 _database_code_depnum_ccdc_archive 'CCDC 629937' _audit_creation_method SHELXL-97 _chemical_name_systematic (E,E)-2-(3-formylbenzylidene)-6-(4-methoxybenzylidene)cyclohexanone _chemical_name_common ;(E,E)-2-(3-formylbenzylidene)-6-(4- methoxybenzylidene)cyclohexanone ; _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 03' _chemical_formula_sum 'C22 H20 O3' _chemical_formula_weight 332.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.0672(8) _cell_length_b 14.9408(8) _cell_length_c 7.1505(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.855(2) _cell_angle_gamma 90.00 _cell_volume 1704.26(14) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8687 _exptl_absorpt_correction_T_max 0.9586 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9948 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.96 _diffrn_reflns_theta_max 25.40 _reflns_number_total 3100 _reflns_number_gt 2222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement 'Nonius collect' _computing_data_reduction 'Nonius collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material ciftab _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^)+(0.0363P)^2^+0.4744P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3100 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O24 O 0.90089(8) 0.92672(9) 0.18412(16) 0.0348(3) Uani 1 1 d . . . O23 O 0.51023(8) 0.87496(10) -0.67092(18) 0.0412(4) Uani 1 1 d . . . C6 C 1.02501(11) 0.87851(12) 0.0645(2) 0.0254(4) Uani 1 1 d . . . C2 C 0.87920(11) 0.87504(12) -0.1322(2) 0.0266(4) Uani 1 1 d . . . C16 C 0.72550(11) 0.87960(12) -0.2807(2) 0.0279(4) Uani 1 1 d . . . C8 C 1.15695(11) 0.88229(13) 0.3050(2) 0.0265(4) Uani 1 1 d . . . C20 C 0.58042(12) 0.91989(14) -0.3805(3) 0.0340(5) Uani 1 1 d . . . H20 H 0.5307 0.9497 -0.3556 0.041 Uiso 1 1 calc R . . C13 C 1.18769(11) 0.92733(13) 0.4704(2) 0.0279(4) Uani 1 1 d . . . H13 H 1.1514 0.9664 0.5272 0.034 Uiso 1 1 calc R . . C3 C 0.92074(11) 0.83892(14) -0.2953(2) 0.0321(5) Uani 1 1 d . . . H3A H 0.8893 0.8598 -0.4149 0.038 Uiso 1 1 calc R . . H3B H 0.9183 0.7727 -0.2939 0.038 Uiso 1 1 calc R . . C15 C 0.79632(11) 0.89015(12) -0.1357(2) 0.0282(4) Uani 1 1 d . . . H15 H 0.7811 0.9122 -0.0198 0.034 Uiso 1 1 calc R . . C1 C 0.93232(11) 0.89647(12) 0.0477(2) 0.0267(4) Uani 1 1 d . . . C21 C 0.65055(11) 0.92324(13) -0.2511(3) 0.0313(5) Uani 1 1 d . . . H21 H 0.6485 0.9560 -0.1380 0.038 Uiso 1 1 calc R . . C7 C 1.06874(11) 0.89526(12) 0.2331(2) 0.0264(4) Uani 1 1 d . . . H7 H 1.0361 0.9203 0.3225 0.032 Uiso 1 1 calc R . . C11 C 1.32370(12) 0.86017(14) 0.4719(3) 0.0342(5) Uani 1 1 d . . . H11 H 1.3802 0.8536 0.5265 0.041 Uiso 1 1 calc R . . O25 O 1.36503(9) 0.95463(11) 0.8238(2) 0.0512(4) Uani 1 1 d . . . C5 C 1.06262(11) 0.84338(13) -0.1052(2) 0.0299(4) Uani 1 1 d . . . H5A H 1.1200 0.8678 -0.1043 0.036 Uiso 1 1 calc R . . H5B H 1.0670 0.7774 -0.0965 0.036 Uiso 1 1 calc R . . C18 C 0.65395(12) 0.82604(14) -0.5797(3) 0.0349(5) Uani 1 1 d . . . H18 H 0.6550 0.7919 -0.6915 0.042 Uiso 1 1 calc R . . C12 C 1.26942(11) 0.91683(13) 0.5539(2) 0.0301(4) Uani 1 1 d . . . C9 C 1.21239(11) 0.82377(14) 0.2282(3) 0.0330(5) Uani 1 1 d . . . H9 H 1.1934 0.7906 0.1180 0.040 Uiso 1 1 calc R . . C19 C 0.58187(11) 0.87299(14) -0.5484(3) 0.0324(5) Uani 1 1 d . . . C4 C 1.01126(11) 0.86821(13) -0.2883(2) 0.0302(4) Uani 1 1 d . . . H4A H 1.0363 0.8401 -0.3938 0.036 Uiso 1 1 calc R . . H4B H 1.0132 0.9339 -0.3051 0.036 Uiso 1 1 calc R . . C14 C 1.29714(13) 0.96366(15) 0.7303(3) 0.0393(5) Uani 1 1 d . . . H14 H 1.2589 1.0045 0.7756 0.047 Uiso 1 1 calc R . . C17 C 0.72385(12) 0.82951(13) -0.4471(3) 0.0331(5) Uani 1 1 d . . . H17 H 0.7725 0.7969 -0.4694 0.040 Uiso 1 1 calc R . . C10 C 1.29442(12) 0.81378(14) 0.3108(3) 0.0367(5) Uani 1 1 d . . . H10 H 1.3310 0.7744 0.2556 0.044 Uiso 1 1 calc R . . C22 C 0.51169(13) 0.83758(18) -0.8542(3) 0.0500(6) Uani 1 1 d . . . H22A H 0.5585 0.8634 -0.9124 0.075 Uiso 1 1 calc R . . H22B H 0.4588 0.8512 -0.9322 0.075 Uiso 1 1 calc R . . H22C H 0.5188 0.7726 -0.8439 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O24 0.0365(7) 0.0420(9) 0.0278(7) -0.0059(6) 0.0119(6) 0.0053(6) O23 0.0344(7) 0.0517(10) 0.0375(8) -0.0119(7) 0.0043(6) 0.0023(7) C6 0.0341(10) 0.0178(10) 0.0262(9) 0.0035(8) 0.0112(8) 0.0020(8) C2 0.0349(10) 0.0210(10) 0.0253(9) 0.0009(8) 0.0093(8) -0.0007(8) C16 0.0330(10) 0.0238(10) 0.0288(9) -0.0008(8) 0.0113(8) -0.0007(8) C8 0.0324(10) 0.0248(11) 0.0239(9) 0.0050(8) 0.0102(8) -0.0008(8) C20 0.0328(10) 0.0340(12) 0.0371(11) -0.0047(9) 0.0126(9) 0.0019(9) C13 0.0343(10) 0.0250(10) 0.0265(9) 0.0034(8) 0.0120(8) 0.0012(8) C3 0.0374(11) 0.0334(12) 0.0271(9) -0.0053(9) 0.0108(8) 0.0000(9) C15 0.0384(11) 0.0222(10) 0.0256(9) -0.0010(8) 0.0104(8) 0.0004(8) C1 0.0357(10) 0.0209(10) 0.0255(9) 0.0015(8) 0.0113(8) 0.0018(8) C21 0.0368(11) 0.0294(11) 0.0291(10) -0.0043(8) 0.0104(8) -0.0030(9) C7 0.0345(10) 0.0218(10) 0.0247(9) 0.0033(8) 0.0116(8) 0.0038(8) C11 0.0318(10) 0.0383(12) 0.0337(10) 0.0013(9) 0.0082(8) 0.0003(9) O25 0.0463(9) 0.0663(12) 0.0395(8) -0.0086(8) -0.0008(7) 0.0007(8) C5 0.0338(10) 0.0295(11) 0.0281(10) -0.0001(8) 0.0111(8) 0.0017(8) C18 0.0371(11) 0.0349(12) 0.0341(11) -0.0105(9) 0.0098(9) -0.0026(9) C12 0.0357(11) 0.0294(11) 0.0267(9) 0.0026(8) 0.0096(8) -0.0040(8) C9 0.0379(11) 0.0311(12) 0.0315(10) -0.0038(9) 0.0105(8) 0.0035(9) C19 0.0311(10) 0.0323(12) 0.0344(10) -0.0038(9) 0.0069(8) -0.0034(9) C4 0.0385(10) 0.0293(11) 0.0253(9) -0.0024(8) 0.0148(8) 0.0025(9) C14 0.0381(12) 0.0463(14) 0.0341(11) -0.0035(10) 0.0072(9) 0.0008(10) C17 0.0339(10) 0.0307(12) 0.0367(11) -0.0058(9) 0.0118(9) 0.0012(9) C10 0.0327(11) 0.0407(13) 0.0383(11) -0.0053(9) 0.0110(9) 0.0076(9) C22 0.0456(13) 0.0671(18) 0.0371(12) -0.0165(11) 0.0045(10) -0.0008(11) _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 O24 C1 1.236(2) . ? O23 C19 1.361(2) . ? O23 C22 1.427(2) . ? C6 C7 1.344(2) . ? C6 C1 1.504(2) . ? C6 C5 1.513(2) . ? C2 C15 1.348(2) . ? C2 C1 1.491(2) . ? C2 C3 1.511(2) . ? C16 C17 1.403(2) . ? C16 C21 1.407(3) . ? C16 C15 1.454(2) . ? C8 C13 1.398(2) . ? C8 C9 1.406(3) . ? C8 C7 1.462(2) . ? C20 C21 1.371(3) . ? C20 C19 1.392(3) . ? C13 C12 1.385(3) . ? C3 C4 1.514(2) . ? C11 C10 1.378(3) . ? C11 C12 1.394(3) . ? O25 C14 1.217(2) . ? C5 C4 1.508(2) . ? C18 C17 1.381(3) . ? C18 C19 1.395(3) . ? C12 C14 1.465(3) . ? C9 C10 1.387(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 O23 C22 118.51(15) . . ? C7 C6 C1 116.41(15) . . ? C7 C6 C5 124.61(16) . . ? C1 C6 C5 118.98(15) . . ? C15 C2 C1 116.25(15) . . ? C15 C2 C3 124.89(16) . . ? C1 C2 C3 118.86(15) . . ? C17 C16 C21 116.40(16) . . ? C17 C16 C15 126.64(16) . . ? C21 C16 C15 116.95(16) . . ? C13 C8 C9 116.96(16) . . ? C13 C8 C7 117.61(16) . . ? C9 C8 C7 125.30(16) . . ? C21 C20 C19 120.21(17) . . ? C12 C13 C8 122.08(17) . . ? C2 C3 C4 112.47(15) . . ? C2 C15 C16 133.02(16) . . ? O24 C1 C2 120.90(16) . . ? O24 C1 C6 119.76(16) . . ? C2 C1 C6 119.32(15) . . ? C20 C21 C16 122.05(17) . . ? C6 C7 C8 132.20(16) . . ? C10 C11 C12 119.25(17) . . ? C4 C5 C6 112.42(15) . . ? C17 C18 C19 119.58(17) . . ? C13 C12 C11 119.74(17) . . ? C13 C12 C14 119.50(17) . . ? C11 C12 C14 120.74(17) . . ? C10 C9 C8 120.97(18) . . ? O23 C19 C20 116.37(16) . . ? O23 C19 C18 124.20(17) . . ? C20 C19 C18 119.42(17) . . ? C5 C4 C3 112.45(15) . . ? O25 C14 C12 125.50(19) . . ? C18 C17 C16 122.23(17) . . ? C11 C10 C9 120.96(18) . . ? 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 C9 C8 C13 C12 1.3(3) . . . . ? C7 C8 C13 C12 177.46(16) . . . . ? C15 C2 C3 C4 153.21(18) . . . . ? C1 C2 C3 C4 -26.6(2) . . . . ? C1 C2 C15 C16 178.94(19) . . . . ? C3 C2 C15 C16 -0.8(3) . . . . ? C17 C16 C15 C2 16.6(3) . . . . ? C21 C16 C15 C2 -164.1(2) . . . . ? C15 C2 C1 O24 -0.3(3) . . . . ? C3 C2 C1 O24 179.50(17) . . . . ? C15 C2 C1 C6 177.98(16) . . . . ? C3 C2 C1 C6 -2.2(2) . . . . ? C7 C6 C1 O24 1.4(3) . . . . ? C5 C6 C1 O24 -178.69(17) . . . . ? C7 C6 C1 C2 -176.92(16) . . . . ? C5 C6 C1 C2 3.0(2) . . . . ? C19 C20 C21 C16 -0.6(3) . . . . ? C17 C16 C21 C20 -2.3(3) . . . . ? C15 C16 C21 C20 178.30(17) . . . . ? C1 C6 C7 C8 176.55(18) . . . . ? C5 C6 C7 C8 -3.4(3) . . . . ? C13 C8 C7 C6 163.85(19) . . . . ? C9 C8 C7 C6 -20.4(3) . . . . ? C7 C6 C5 C4 -154.94(18) . . . . ? C1 C6 C5 C4 25.1(2) . . . . ? C8 C13 C12 C11 0.3(3) . . . . ? C8 C13 C12 C14 -178.07(17) . . . . ? C10 C11 C12 C13 -1.5(3) . . . . ? C10 C11 C12 C14 176.87(18) . . . . ? C13 C8 C9 C10 -1.9(3) . . . . ? C7 C8 C9 C10 -177.65(18) . . . . ? C22 O23 C19 C20 172.26(19) . . . . ? C22 O23 C19 C18 -9.2(3) . . . . ? C21 C20 C19 O23 -178.41(17) . . . . ? C21 C20 C19 C18 3.0(3) . . . . ? C17 C18 C19 O23 179.07(18) . . . . ? C17 C18 C19 C20 -2.4(3) . . . . ? C6 C5 C4 C3 -54.8(2) . . . . ? C2 C3 C4 C5 55.7(2) . . . . ? C13 C12 C14 O25 174.2(2) . . . . ? C11 C12 C14 O25 -4.1(3) . . . . ? C19 C18 C17 C16 -0.5(3) . . . . ? C21 C16 C17 C18 2.8(3) . . . . ? C15 C16 C17 C18 -177.81(19) . . . . ? C12 C11 C10 C9 1.0(3) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.193 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.038 # Attachment 'rigid female union 32.cif' data_32 _database_code_depnum_ccdc_archive 'CCDC 630660' _audit_creation_method SHELXL-97 _chemical_name_systematic ;3,3'-(1E,1'E)-(2-oxocyclohexane-1,3-diylidene)bis(methan-1-yl-1-ylidene)- bis(2-methoxy-5-methylbenzaldehyde) ; _chemical_name_common ; 3,3'-(1E,1'E)-(2-oxocyclohexane-1,3-diylidene)bis(methan-1-yl- 1-ylidene)-bis(2-methoxy-5-methylbenzaldehyde) ; _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 O5' _chemical_formula_sum 'C26 H26 O5' _chemical_formula_weight 418.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _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 11.446(2) _cell_length_b 15.395(3) _cell_length_c 12.411(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.07(3) _cell_angle_gamma 90.00 _cell_volume 2185.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _exptl_crystal_description plate _exptl_crystal_colour lime _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.087 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 10031 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 28.29 _reflns_number_total 5375 _reflns_number_gt 3183 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement 'Nonius collect' _computing_data_reduction 'Nonius collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material ciftab _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^)+(0.0664P)^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_extinction_coef ? _refine_ls_number_reflns 5375 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0991 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O4 O 0.54982(9) 0.17566(7) 0.87641(8) 0.0315(3) Uani 1 1 d . . . O1 O 0.67945(11) 0.44087(7) 1.00128(9) 0.0411(3) Uani 1 1 d . . . O3 O 1.12661(10) 0.88945(7) 0.98231(9) 0.0396(3) Uani 1 1 d . . . O2 O 0.99049(10) 0.64578(7) 0.96837(8) 0.0357(3) Uani 1 1 d . . . O5 O 0.34145(11) 0.00444(7) 0.71712(10) 0.0442(3) Uani 1 1 d . . . C18 C 0.42880(14) 0.29814(9) 0.82372(11) 0.0258(3) Uani 1 1 d . . . C6 C 0.53533(13) 0.43993(9) 0.85871(11) 0.0257(3) Uani 1 1 d . . . C8 C 0.79342(14) 0.69905(9) 0.96517(12) 0.0271(4) Uani 1 1 d . . . C7 C 0.75018(14) 0.60873(9) 0.96690(12) 0.0279(3) Uani 1 1 d . . . H7 H 0.7923 0.5695 1.0129 0.033 Uiso 1 1 calc R . . C23 C 0.32258(13) 0.32636(10) 0.77602(11) 0.0280(4) Uani 1 1 d . . . H23 H 0.3030 0.3862 0.7804 0.034 Uiso 1 1 calc R . . C21 C 0.27298(14) 0.18290(10) 0.71779(12) 0.0307(4) Uani 1 1 d . . . H21 H 0.2216 0.1439 0.6803 0.037 Uiso 1 1 calc R . . C2 C 0.65821(13) 0.57584(9) 0.91092(11) 0.0261(3) Uani 1 1 d . . . C1 C 0.62863(14) 0.48200(9) 0.92939(11) 0.0276(4) Uani 1 1 d . . . C19 C 0.45245(13) 0.20863(9) 0.82064(12) 0.0270(4) Uani 1 1 d . . . C3 C 0.58398(14) 0.62516(10) 0.82878(12) 0.0301(4) Uani 1 1 d . . . H3A H 0.6283 0.6758 0.8030 0.036 Uiso 1 1 calc R . . H3B H 0.5130 0.6471 0.8631 0.036 Uiso 1 1 calc R . . C17 C 0.51340(13) 0.35570(9) 0.87884(11) 0.0265(3) Uani 1 1 d . . . H17 H 0.5587 0.3303 0.9363 0.032 Uiso 1 1 calc R . . C22 C 0.24466(14) 0.27033(10) 0.72258(12) 0.0297(4) Uani 1 1 d . . . C13 C 0.71856(15) 0.77068(10) 0.96057(12) 0.0298(4) Uani 1 1 d . . . H13 H 0.6366 0.7607 0.9570 0.036 Uiso 1 1 calc R . . C10 C 0.95721(14) 0.80026(10) 0.97163(12) 0.0295(4) Uani 1 1 d . . . C9 C 0.91408(14) 0.71507(10) 0.97114(11) 0.0288(4) Uani 1 1 d . . . C20 C 0.37616(14) 0.15126(9) 0.76730(11) 0.0285(4) Uani 1 1 d . . . C5 C 0.47455(14) 0.49225(9) 0.77034(12) 0.0296(4) Uani 1 1 d . . . H5A H 0.3999 0.5149 0.7968 0.035 Uiso 1 1 calc R . . H5B H 0.4561 0.4538 0.7081 0.035 Uiso 1 1 calc R . . C11 C 0.87870(14) 0.86968(10) 0.96726(11) 0.0321(4) Uani 1 1 d . . . H11 H 0.9081 0.9274 0.9686 0.039 Uiso 1 1 calc R . . C12 C 0.75896(15) 0.85640(10) 0.96095(12) 0.0318(4) Uani 1 1 d . . . C25 C 0.40467(15) 0.05842(10) 0.75934(13) 0.0372(4) Uani 1 1 d . . . H25 H 0.4778 0.0396 0.7895 0.045 Uiso 1 1 calc R . . C15 C 1.08392(15) 0.81697(11) 0.97629(12) 0.0348(4) Uani 1 1 d . . . H15 H 1.1353 0.7686 0.9745 0.042 Uiso 1 1 calc R . . C26 C 0.13486(15) 0.30517(11) 0.66743(15) 0.0410(4) Uani 1 1 d . . . H26A H 0.1242 0.2782 0.5962 0.062 Uiso 1 1 calc R . . H26B H 0.1415 0.3683 0.6592 0.062 Uiso 1 1 calc R . . H26C H 0.0675 0.2917 0.7110 0.062 Uiso 1 1 calc R . . C4 C 0.54847(15) 0.56774(10) 0.73347(12) 0.0335(4) Uani 1 1 d . . . H4A H 0.5034 0.6024 0.6791 0.040 Uiso 1 1 calc R . . H4B H 0.6193 0.5453 0.6994 0.040 Uiso 1 1 calc R . . C24 C 0.65593(15) 0.17981(11) 0.81843(14) 0.0402(4) Uani 1 1 d . . . H24A H 0.6485 0.1432 0.7540 0.060 Uiso 1 1 calc R . . H24B H 0.7213 0.1591 0.8647 0.060 Uiso 1 1 calc R . . H24C H 0.6705 0.2400 0.7970 0.060 Uiso 1 1 calc R . . C16 C 0.67401(16) 0.93119(11) 0.95415(15) 0.0433(4) Uani 1 1 d . . . H16A H 0.7048 0.9797 0.9976 0.065 Uiso 1 1 calc R . . H16B H 0.5987 0.9128 0.9815 0.065 Uiso 1 1 calc R . . H16C H 0.6633 0.9497 0.8789 0.065 Uiso 1 1 calc R . . C14 C 1.03722(17) 0.61786(12) 1.07142(15) 0.0471(5) Uani 1 1 d . . . H14A H 1.0755 0.6670 1.1085 0.071 Uiso 1 1 calc R . . H14B H 1.0944 0.5715 1.0613 0.071 Uiso 1 1 calc R . . H14C H 0.9737 0.5961 1.1149 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O4 0.0280(6) 0.0290(6) 0.0372(6) 0.0018(5) -0.0044(5) 0.0004(5) O1 0.0458(8) 0.0308(6) 0.0451(6) 0.0061(5) -0.0194(6) -0.0065(6) O3 0.0357(7) 0.0416(7) 0.0416(7) -0.0026(5) 0.0004(5) -0.0131(6) O2 0.0304(7) 0.0337(6) 0.0429(7) -0.0040(5) -0.0010(5) 0.0016(5) O5 0.0454(8) 0.0260(6) 0.0605(8) -0.0050(6) -0.0086(6) -0.0034(6) C18 0.0260(9) 0.0252(8) 0.0263(7) -0.0009(6) 0.0021(6) -0.0037(6) C6 0.0224(8) 0.0255(8) 0.0291(7) -0.0028(6) 0.0010(6) -0.0005(6) C8 0.0282(9) 0.0268(8) 0.0263(7) -0.0028(6) -0.0009(6) -0.0042(7) C7 0.0271(9) 0.0260(8) 0.0307(8) -0.0009(6) 0.0017(7) 0.0009(7) C23 0.0280(9) 0.0232(8) 0.0328(8) -0.0001(6) 0.0012(7) -0.0002(7) C21 0.0268(9) 0.0280(8) 0.0372(8) -0.0040(7) -0.0014(7) -0.0043(7) C2 0.0249(8) 0.0249(8) 0.0284(7) -0.0026(6) 0.0014(6) -0.0004(7) C1 0.0255(9) 0.0270(8) 0.0302(8) -0.0006(6) -0.0007(7) -0.0005(7) C19 0.0249(9) 0.0274(8) 0.0288(8) 0.0018(6) 0.0009(6) 0.0010(7) C3 0.0277(9) 0.0258(8) 0.0366(8) 0.0032(7) -0.0020(7) -0.0038(7) C17 0.0247(8) 0.0275(8) 0.0271(7) -0.0015(6) -0.0009(6) 0.0005(7) C22 0.0247(9) 0.0291(8) 0.0350(8) 0.0000(7) -0.0018(7) -0.0034(7) C13 0.0266(9) 0.0314(8) 0.0311(8) -0.0011(7) -0.0011(7) -0.0047(7) C10 0.0288(9) 0.0340(9) 0.0256(8) -0.0018(6) -0.0013(6) -0.0067(7) C9 0.0305(10) 0.0297(8) 0.0260(8) -0.0039(6) -0.0008(7) 0.0000(7) C20 0.0299(9) 0.0230(8) 0.0327(8) -0.0024(6) 0.0022(7) -0.0018(7) C5 0.0286(9) 0.0280(8) 0.0317(8) 0.0010(6) -0.0051(7) -0.0036(7) C11 0.0359(10) 0.0289(8) 0.0314(8) 0.0006(7) -0.0008(7) -0.0086(7) C12 0.0352(10) 0.0275(8) 0.0326(8) -0.0001(7) -0.0005(7) -0.0030(7) C25 0.0342(10) 0.0273(9) 0.0495(10) -0.0028(7) -0.0060(8) 0.0005(8) C15 0.0354(10) 0.0368(10) 0.0322(8) -0.0016(7) 0.0015(7) -0.0062(8) C26 0.0318(10) 0.0297(9) 0.0604(11) -0.0042(8) -0.0139(8) -0.0023(7) C4 0.0335(10) 0.0329(9) 0.0334(8) 0.0052(7) -0.0067(7) -0.0069(7) C24 0.0281(10) 0.0430(10) 0.0492(10) -0.0012(8) -0.0010(8) 0.0050(8) C16 0.0399(11) 0.0301(9) 0.0595(11) 0.0021(8) -0.0014(9) -0.0008(8) C14 0.0391(11) 0.0462(11) 0.0554(11) 0.0077(9) -0.0084(9) 0.0044(9) _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 O4 C19 1.3867(18) . ? O4 C24 1.435(2) . ? O1 C1 1.2238(17) . ? O3 C15 1.2195(18) . ? O2 C9 1.3807(18) . ? O2 C14 1.434(2) . ? O5 C25 1.2089(19) . ? C18 C23 1.402(2) . ? C18 C19 1.405(2) . ? C18 C17 1.464(2) . ? C6 C17 1.346(2) . ? C6 C1 1.504(2) . ? C6 C5 1.510(2) . ? C8 C13 1.396(2) . ? C8 C9 1.402(2) . ? C8 C7 1.476(2) . ? C7 C2 1.340(2) . ? C23 C22 1.392(2) . ? C21 C22 1.386(2) . ? C21 C20 1.399(2) . ? C2 C1 1.503(2) . ? C2 C3 1.508(2) . ? C19 C20 1.392(2) . ? C3 C4 1.520(2) . ? C22 C26 1.508(2) . ? C13 C12 1.398(2) . ? C10 C11 1.396(2) . ? C10 C9 1.401(2) . ? C10 C15 1.472(2) . ? C20 C25 1.470(2) . ? C5 C4 1.518(2) . ? C11 C12 1.385(2) . ? C12 C16 1.507(2) . ? 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 C19 O4 C24 114.39(11) . . ? C9 O2 C14 115.18(12) . . ? C23 C18 C19 117.22(13) . . ? C23 C18 C17 123.97(14) . . ? C19 C18 C17 118.78(13) . . ? C17 C6 C1 116.10(13) . . ? C17 C6 C5 124.37(13) . . ? C1 C6 C5 119.52(13) . . ? C13 C8 C9 117.71(14) . . ? C13 C8 C7 122.60(14) . . ? C9 C8 C7 119.66(14) . . ? C2 C7 C8 127.31(14) . . ? C22 C23 C18 122.71(14) . . ? C22 C21 C20 120.95(14) . . ? C7 C2 C1 117.47(13) . . ? C7 C2 C3 124.97(14) . . ? C1 C2 C3 117.54(13) . . ? O1 C1 C2 120.31(13) . . ? O1 C1 C6 120.74(13) . . ? C2 C1 C6 118.95(13) . . ? O4 C19 C20 118.95(13) . . ? O4 C19 C18 119.83(13) . . ? C20 C19 C18 121.12(14) . . ? C2 C3 C4 111.18(13) . . ? C6 C17 C18 128.40(14) . . ? C21 C22 C23 118.39(14) . . ? C21 C22 C26 121.22(14) . . ? C23 C22 C26 120.34(14) . . ? C8 C13 C12 122.87(15) . . ? C11 C10 C9 119.35(15) . . ? C11 C10 C15 119.97(14) . . ? C9 C10 C15 120.68(15) . . ? O2 C9 C10 119.99(14) . . ? O2 C9 C8 119.10(13) . . ? C10 C9 C8 120.73(14) . . ? C19 C20 C21 119.53(14) . . ? C19 C20 C25 120.78(14) . . ? C21 C20 C25 119.66(14) . . ? C6 C5 C4 112.34(13) . . ? C12 C11 C10 121.56(15) . . ? C11 C12 C13 117.77(15) . . ? C11 C12 C16 121.69(15) . . ? C13 C12 C16 120.54(15) . . ? O5 C25 C20 124.51(15) . . ? O3 C15 C10 123.67(16) . . ? C5 C4 C3 110.30(13) . . ? 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 C13 C8 C7 C2 39.2(2) . . . . ? C9 C8 C7 C2 -142.45(16) . . . . ? C19 C18 C23 C22 -3.1(2) . . . . ? C17 C18 C23 C22 178.92(14) . . . . ? C8 C7 C2 C1 -177.83(14) . . . . ? C8 C7 C2 C3 3.8(3) . . . . ? C7 C2 C1 O1 7.6(2) . . . . ? C3 C2 C1 O1 -173.86(15) . . . . ? C7 C2 C1 C6 -172.76(13) . . . . ? C3 C2 C1 C6 5.7(2) . . . . ? C17 C6 C1 O1 -0.8(2) . . . . ? C5 C6 C1 O1 -179.73(15) . . . . ? C17 C6 C1 C2 179.61(14) . . . . ? C5 C6 C1 C2 0.7(2) . . . . ? C24 O4 C19 C20 98.48(16) . . . . ? C24 O4 C19 C18 -85.05(17) . . . . ? C23 C18 C19 O4 -173.04(13) . . . . ? C17 C18 C19 O4 5.0(2) . . . . ? C23 C18 C19 C20 3.3(2) . . . . ? C17 C18 C19 C20 -178.60(14) . . . . ? C7 C2 C3 C4 141.65(16) . . . . ? C1 C2 C3 C4 -36.73(19) . . . . ? C1 C6 C17 C18 -179.74(14) . . . . ? C5 C6 C17 C18 -0.9(3) . . . . ? C23 C18 C17 C6 -30.6(2) . . . . ? C19 C18 C17 C6 151.45(16) . . . . ? C20 C21 C22 C23 1.3(2) . . . . ? C20 C21 C22 C26 178.70(15) . . . . ? C18 C23 C22 C21 0.9(2) . . . . ? C18 C23 C22 C26 -176.55(15) . . . . ? C9 C8 C13 C12 0.4(2) . . . . ? C7 C8 C13 C12 178.77(14) . . . . ? C14 O2 C9 C10 85.90(18) . . . . ? C14 O2 C9 C8 -98.90(16) . . . . ? C11 C10 C9 O2 175.80(12) . . . . ? C15 C10 C9 O2 -4.0(2) . . . . ? C11 C10 C9 C8 0.7(2) . . . . ? C15 C10 C9 C8 -179.10(13) . . . . ? C13 C8 C9 O2 -175.62(12) . . . . ? C7 C8 C9 O2 6.0(2) . . . . ? C13 C8 C9 C10 -0.5(2) . . . . ? C7 C8 C9 C10 -178.83(13) . . . . ? O4 C19 C20 C21 175.08(14) . . . . ? C18 C19 C20 C21 -1.3(2) . . . . ? O4 C19 C20 C25 -7.0(2) . . . . ? C18 C19 C20 C25 176.60(14) . . . . ? C22 C21 C20 C19 -1.1(2) . . . . ? C22 C21 C20 C25 -179.04(15) . . . . ? C17 C6 C5 C4 -154.45(15) . . . . ? C1 C6 C5 C4 24.4(2) . . . . ? C9 C10 C11 C12 -0.9(2) . . . . ? C15 C10 C11 C12 178.89(14) . . . . ? C10 C11 C12 C13 0.9(2) . . . . ? C10 C11 C12 C16 -178.85(14) . . . . ? C8 C13 C12 C11 -0.6(2) . . . . ? C8 C13 C12 C16 179.08(14) . . . . ? C19 C20 C25 O5 177.78(16) . . . . ? C21 C20 C25 O5 -4.3(3) . . . . ? C11 C10 C15 O3 4.0(2) . . . . ? C9 C10 C15 O3 -176.23(14) . . . . ? C6 C5 C4 C3 -55.61(18) . . . . ? C2 C3 C4 C5 62.18(18) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.200 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.046 # Attachment 'flexible male union 40.cif' data_40 _database_code_depnum_ccdc_archive 'CCDC 630661' _audit_creation_method SHELXL-97 _chemical_name_systematic ;(2E,2'E)-2,2'-(2,2'-(ethane-1,2-diylbis(oxy))bis(2,1-phenylene))- bis(methan-1-yl-1-ylidene)dicyclohexanone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H30 O4' _chemical_formula_sum 'C28 H30 O4' _chemical_formula_weight 430.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _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 14.1051(5) _cell_length_b 5.9840(2) _cell_length_c 14.3719(6) _cell_angle_alpha 90.00 _cell_angle_beta 114.297(2) _cell_angle_gamma 90.00 _cell_volume 1105.61(7) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.085 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 5037 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0841 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2677 _reflns_number_gt 1336 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement 'Nonius collect' _computing_data_reduction 'Nonius collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material ciftab _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^)+(0.0652P)^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_extinction_coef ? _refine_ls_number_reflns 2677 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1256 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.62053(8) 0.6397(2) 0.02888(9) 0.0456(4) Uani 1 1 d . . . C9 C 0.72149(11) 0.6465(3) 0.09984(12) 0.0368(4) Uani 1 1 d . . . C13 C 0.88382(12) 0.8466(3) 0.16320(13) 0.0402(5) Uani 1 1 d . . . H13 H 0.9246 0.9720 0.1619 0.048 Uiso 1 1 calc R . . C8 C 0.77970(12) 0.8318(3) 0.09145(12) 0.0361(4) Uani 1 1 d . . . C12 C 0.92774(12) 0.6812(3) 0.23560(13) 0.0424(5) Uani 1 1 d . . . H12 H 0.9987 0.6921 0.2820 0.051 Uiso 1 1 calc R . . C10 C 0.76531(12) 0.4846(3) 0.17385(13) 0.0395(5) Uani 1 1 d . . . H10 H 0.7244 0.3629 0.1788 0.047 Uiso 1 1 calc R . . C2 C 0.76561(12) 1.1518(3) -0.03171(13) 0.0419(5) Uani 1 1 d . . . O1 O 0.59432(10) 1.2568(2) -0.14445(11) 0.0665(5) Uani 1 1 d . . . C14 C 0.55262(12) 0.4765(3) 0.04199(13) 0.0430(5) Uani 1 1 d . . . H14A H 0.5507 0.4923 0.1098 0.052 Uiso 1 1 calc R . . H14B H 0.5759 0.3234 0.0357 0.052 Uiso 1 1 calc R . . C3 C 0.88007(13) 1.1945(3) -0.00361(14) 0.0462(5) Uani 1 1 d . . . H3A H 0.9172 1.0497 0.0093 0.055 Uiso 1 1 calc R . . H3B H 0.9091 1.2823 0.0604 0.055 Uiso 1 1 calc R . . C11 C 0.86936(12) 0.5007(3) 0.24095(13) 0.0419(5) Uani 1 1 d . . . H11 H 0.9003 0.3873 0.2905 0.050 Uiso 1 1 calc R . . C7 C 0.72771(13) 0.9948(3) 0.01110(13) 0.0402(5) Uani 1 1 d . . . H7 H 0.6539 0.9895 -0.0159 0.048 Uiso 1 1 calc R . . C4 C 0.89953(15) 1.3193(4) -0.08604(15) 0.0550(5) Uani 1 1 d . . . H4A H 0.9746 1.3537 -0.0617 0.066 Uiso 1 1 calc R . . H4B H 0.8790 1.2244 -0.1477 0.066 Uiso 1 1 calc R . . C1 C 0.68699(15) 1.2928(3) -0.11305(15) 0.0483(5) Uani 1 1 d . . . C5 C 0.83744(16) 1.5341(4) -0.11249(17) 0.0635(6) Uani 1 1 d . . . H5A H 0.8547 1.6245 -0.0499 0.076 Uiso 1 1 calc R . . H5B H 0.8560 1.6220 -0.1610 0.076 Uiso 1 1 calc R . . C6 C 0.72268(16) 1.4839(4) -0.15965(16) 0.0601(6) Uani 1 1 d . . . H6A H 0.7018 1.4508 -0.2329 0.072 Uiso 1 1 calc R . . H6B H 0.6850 1.6205 -0.1554 0.072 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0301(6) 0.0489(8) 0.0452(7) 0.0093(6) 0.0029(6) -0.0133(5) C9 0.0277(9) 0.0427(11) 0.0365(10) -0.0031(8) 0.0098(8) -0.0033(8) C13 0.0318(9) 0.0472(12) 0.0422(10) -0.0061(9) 0.0158(8) -0.0073(8) C8 0.0319(9) 0.0377(11) 0.0385(10) -0.0047(8) 0.0142(8) -0.0043(8) C12 0.0264(8) 0.0569(13) 0.0403(10) -0.0061(9) 0.0100(8) -0.0012(8) C10 0.0341(9) 0.0406(11) 0.0409(10) -0.0010(8) 0.0126(8) -0.0057(8) C2 0.0406(10) 0.0382(11) 0.0450(10) -0.0052(8) 0.0158(8) -0.0054(8) O1 0.0478(8) 0.0635(11) 0.0686(10) 0.0130(8) 0.0044(7) -0.0042(7) C14 0.0307(8) 0.0453(12) 0.0455(10) 0.0082(9) 0.0081(8) -0.0092(8) C3 0.0439(10) 0.0443(12) 0.0546(12) -0.0033(9) 0.0245(9) -0.0064(9) C11 0.0334(9) 0.0456(12) 0.0413(10) 0.0003(9) 0.0100(8) 0.0040(8) C7 0.0336(9) 0.0418(12) 0.0419(10) -0.0044(9) 0.0123(8) -0.0063(8) C4 0.0633(12) 0.0513(14) 0.0609(13) -0.0078(10) 0.0362(10) -0.0090(10) C1 0.0461(11) 0.0451(13) 0.0492(11) -0.0035(9) 0.0148(9) -0.0058(9) C5 0.0698(14) 0.0540(14) 0.0737(15) 0.0128(11) 0.0367(12) -0.0045(11) C6 0.0701(14) 0.0480(14) 0.0596(13) 0.0078(11) 0.0240(11) -0.0030(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C9 1.3691(17) . ? O2 C14 1.4336(19) . ? C9 C10 1.382(2) . ? C9 C8 1.414(2) . ? C13 C12 1.384(3) . ? C13 C8 1.408(2) . ? C8 C7 1.458(3) . ? C12 C11 1.380(3) . ? C10 C11 1.389(2) . ? C2 C7 1.348(2) . ? C2 C1 1.497(3) . ? C2 C3 1.516(2) . ? O1 C1 1.214(2) . ? C14 C14 1.505(3) 3_665 ? C3 C4 1.518(3) . ? C4 C5 1.513(3) . ? C1 C6 1.512(3) . ? C5 C6 1.506(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O2 C14 117.95(13) . . ? O2 C9 C10 123.45(16) . . ? O2 C9 C8 114.98(15) . . ? C10 C9 C8 121.57(14) . . ? C12 C13 C8 121.00(17) . . ? C13 C8 C9 117.01(16) . . ? C13 C8 C7 124.83(16) . . ? C9 C8 C7 118.14(14) . . ? C11 C12 C13 120.60(15) . . ? C9 C10 C11 119.75(16) . . ? C7 C2 C1 116.34(15) . . ? C7 C2 C3 125.09(16) . . ? C1 C2 C3 118.57(17) . . ? O2 C14 C14 105.03(17) . 3_665 ? C2 C3 C4 112.95(16) . . ? C12 C11 C10 119.99(17) . . ? C2 C7 C8 131.52(16) . . ? C5 C4 C3 110.00(17) . . ? O1 C1 C2 121.90(18) . . ? O1 C1 C6 118.26(18) . . ? C2 C1 C6 119.83(16) . . ? C6 C5 C4 110.36(18) . . ? C5 C6 C1 116.32(17) . . ? 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 C14 O2 C9 C10 10.2(2) . . . . ? C14 O2 C9 C8 -170.72(16) . . . . ? C12 C13 C8 C9 2.7(3) . . . . ? C12 C13 C8 C7 -178.49(18) . . . . ? O2 C9 C8 C13 179.63(15) . . . . ? C10 C9 C8 C13 -1.3(3) . . . . ? O2 C9 C8 C7 0.8(2) . . . . ? C10 C9 C8 C7 179.87(16) . . . . ? C8 C13 C12 C11 -1.9(3) . . . . ? O2 C9 C10 C11 177.97(16) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C9 O2 C14 C14 175.68(18) . . . 3_665 ? C7 C2 C3 C4 159.96(18) . . . . ? C1 C2 C3 C4 -20.1(2) . . . . ? C13 C12 C11 C10 -0.5(3) . . . . ? C9 C10 C11 C12 2.0(3) . . . . ? C1 C2 C7 C8 -179.37(19) . . . . ? C3 C2 C7 C8 0.6(3) . . . . ? C13 C8 C7 C2 19.8(3) . . . . ? C9 C8 C7 C2 -161.43(19) . . . . ? C2 C3 C4 C5 54.7(2) . . . . ? C7 C2 C1 O1 -5.6(3) . . . . ? C3 C2 C1 O1 174.48(18) . . . . ? C7 C2 C1 C6 175.51(17) . . . . ? C3 C2 C1 C6 -4.4(3) . . . . ? C3 C4 C5 C6 -65.0(2) . . . . ? C4 C5 C6 C1 40.0(3) . . . . ? O1 C1 C6 C5 175.18(19) . . . . ? C2 C1 C6 C5 -5.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.186 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.041 # Attachment 'dienone 43.(CHCl3)0.5.H2O.CIF' data_43_chloroform/water _database_code_depnum_ccdc_archive 'CCDC 630662' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,4:9,10:18,19:25,26-Tetrabenzo-5,8,20,24-tetraoxa-tricyclo[26.3.1.1(12,16)] tritriaconta-1,3,9,11,16,18,25,27-octaene-32,33-dione chloroform water solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C45 H42 O6) (C H Cl3)0.5 (H2 O)' _chemical_formula_sum 'C45.50 H44.50 Cl1.50 O7' _chemical_formula_weight 756.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.1785(2) _cell_length_b 15.0780(2) _cell_length_c 16.5313(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.6450(10) _cell_angle_gamma 90.00 _cell_volume 3749.75(10) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1596 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9273 _exptl_absorpt_correction_T_max 0.9537 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50114 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_sigmaI/netI 0.0790 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 28.20 _reflns_number_total 9001 _reflns_number_gt 5312 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement 'Nonius collect' _computing_data_reduction 'Nonius collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-seed _computing_publication_material ciftab _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. Hydrogens of the water molecule were located from the electron density map and allowed to refine without restraint. ; _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^)+(0.0593P)^2^+2.3241P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9001 _refine_ls_number_parameters 508 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1278 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1308 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl2 Cl 0.59393(5) 0.50560(6) 0.02860(5) 0.0611(3) Uani 1 1 d . . . Cl1 Cl 0.47472(11) 0.63425(10) 0.07785(9) 0.0493(4) Uani 0.50 1 d P . . C1G C 0.4958(4) 0.5626(4) -0.0012(4) 0.0408(14) Uani 0.50 1 d P . . O4 O 0.89530(10) 0.15932(11) 0.20417(11) 0.0322(4) Uani 1 1 d . . . O1 O 1.20637(10) 0.08719(11) 0.21182(11) 0.0324(4) Uani 1 1 d . . . O3 O 0.86285(11) -0.08984(11) 0.02177(10) 0.0315(4) Uani 1 1 d . . . O2 O 1.05782(10) -0.10979(12) 0.02759(10) 0.0327(4) Uani 1 1 d . . . O6 O 1.29022(11) 0.35895(11) 0.12471(12) 0.0379(5) Uani 1 1 d . . . O5 O 0.98925(10) 0.42682(11) 0.12283(11) 0.0313(4) Uani 1 1 d . . . C4 C 1.18954(15) -0.16267(16) 0.10327(14) 0.0251(5) Uani 1 1 d . . . C25 C 1.42272(15) 0.01528(16) 0.10078(15) 0.0260(5) Uani 1 1 d . . . H25A H 1.4802 -0.0073 0.0873 0.031 Uiso 1 1 calc R . . H25B H 1.3892 0.0401 0.0504 0.031 Uiso 1 1 calc R . . C43 C 1.50215(16) 0.43777(18) 0.23520(16) 0.0319(6) Uani 1 1 d . . . H43 H 1.5367 0.4902 0.2447 0.038 Uiso 1 1 calc R . . C45 C 1.48318(16) 0.28185(18) 0.25690(15) 0.0312(6) Uani 1 1 d . . . H45 H 1.5056 0.2276 0.2805 0.037 Uiso 1 1 calc R . . C23 C 1.35284(14) 0.12316(16) 0.18786(13) 0.0228(5) Uani 1 1 d . . . C21 C 1.40022(15) 0.28366(16) 0.20958(15) 0.0258(5) Uani 1 1 d . . . C15 C 0.84572(15) 0.43194(16) 0.16106(14) 0.0245(5) Uani 1 1 d . . . C12 C 0.82067(14) 0.17806(16) 0.16975(14) 0.0237(5) Uani 1 1 d . . . C5 C 1.11252(15) -0.18014(17) 0.04658(15) 0.0276(6) Uani 1 1 d . . . C30 C 1.09916(16) -0.26437(17) 0.01349(16) 0.0318(6) Uani 1 1 d . . . H30 H 1.0483 -0.2764 -0.0250 0.038 Uiso 1 1 calc R . . C38 C 0.77218(16) 0.48186(17) 0.17499(15) 0.0297(6) Uani 1 1 d . . . H38 H 0.7232 0.4528 0.1938 0.036 Uiso 1 1 calc R . . C26 C 1.37002(14) -0.06074(16) 0.13207(15) 0.0272(5) Uani 1 1 d . . . H26A H 1.3606 -0.1077 0.0900 0.033 Uiso 1 1 calc R . . H26B H 1.4045 -0.0866 0.1815 0.033 Uiso 1 1 calc R . . C10 C 0.79388(15) 0.02639(16) 0.12350(14) 0.0247(5) Uani 1 1 d . . . H10 H 0.8569 0.0228 0.1327 0.030 Uiso 1 1 calc R . . C3 C 1.20337(15) -0.07340(16) 0.13662(14) 0.0241(5) Uani 1 1 d . . . H3 H 1.1518 -0.0431 0.1486 0.029 Uiso 1 1 calc R . . C13 C 0.79083(14) 0.27263(16) 0.15899(14) 0.0236(5) Uani 1 1 d . . . C8 C 0.78309(15) -0.11531(17) 0.04438(15) 0.0284(6) Uani 1 1 d . . . C31 C 0.73787(17) -0.19355(17) 0.01848(16) 0.0340(6) Uani 1 1 d . . . H31 H 0.7621 -0.2325 -0.0180 0.041 Uiso 1 1 calc R . . C42 C 1.42053(16) 0.44110(17) 0.18641(16) 0.0310(6) Uani 1 1 d . . . H42 H 1.3992 0.4954 0.1619 0.037 Uiso 1 1 calc R . . C2 C 1.28070(14) -0.02900(15) 0.15244(14) 0.0230(5) Uani 1 1 d . . . C11 C 0.75840(14) 0.10562(16) 0.13666(14) 0.0226(5) Uani 1 1 d . . . C14 C 0.85434(15) 0.33559(16) 0.17357(14) 0.0243(5) Uani 1 1 d . . . H14 H 0.9120 0.3149 0.1946 0.029 Uiso 1 1 calc R . . C32 C 0.65897(17) -0.21396(18) 0.04570(18) 0.0392(7) Uani 1 1 d . . . H32 H 0.6286 -0.2669 0.0275 0.047 Uiso 1 1 calc R . . C20 C 1.37031(14) 0.36424(17) 0.17375(15) 0.0272(6) Uani 1 1 d . . . C1 C 1.27495(15) 0.06207(15) 0.18650(14) 0.0237(5) Uani 1 1 d . . . C36 C 0.65101(15) 0.21815(17) 0.07326(16) 0.0297(6) Uani 1 1 d . . . H36A H 0.6780 0.2151 0.0220 0.036 Uiso 1 1 calc R . . H36B H 0.5870 0.2315 0.0589 0.036 Uiso 1 1 calc R . . C9 C 0.74640(15) -0.05581(16) 0.09647(14) 0.0255(5) Uani 1 1 d . . . C16 C 0.91802(15) 0.47807(16) 0.13540(14) 0.0262(5) Uani 1 1 d . . . C24 C 1.43931(14) 0.08742(17) 0.16487(15) 0.0274(5) Uani 1 1 d . . . H24A H 1.4756 0.0632 0.2141 0.033 Uiso 1 1 calc R . . H24B H 1.4731 0.1364 0.1436 0.033 Uiso 1 1 calc R . . C37 C 0.69500(15) 0.29174(17) 0.12682(16) 0.0302(6) Uani 1 1 d . . . H37A H 0.6920 0.3475 0.0949 0.036 Uiso 1 1 calc R . . H37B H 0.6614 0.3009 0.1735 0.036 Uiso 1 1 calc R . . C41 C 0.91428(16) 0.56961(16) 0.12203(15) 0.0295(6) Uani 1 1 d . . . H41 H 0.9630 0.5998 0.1040 0.035 Uiso 1 1 calc R . . C18 C 1.13996(15) 0.39882(16) 0.11511(17) 0.0313(6) Uani 1 1 d . . . H18A H 1.1261 0.3597 0.0670 0.038 Uiso 1 1 calc R . . H18B H 1.1374 0.3624 0.1646 0.038 Uiso 1 1 calc R . . C22 C 1.33776(15) 0.20832(16) 0.20292(14) 0.0271(5) Uani 1 1 d . . . H22 H 1.2784 0.2224 0.2104 0.033 Uiso 1 1 calc R . . C7 C 0.90539(16) -0.15346(18) -0.02512(16) 0.0344(6) Uani 1 1 d . . . H7A H 0.8667 -0.1671 -0.0767 0.041 Uiso 1 1 calc R . . H7B H 0.9170 -0.2092 0.0062 0.041 Uiso 1 1 calc R . . C17 C 1.07085(15) 0.47057(16) 0.11168(16) 0.0286(6) Uani 1 1 d . . . H17A H 1.0872 0.5147 0.1554 0.034 Uiso 1 1 calc R . . H17B H 1.0649 0.5013 0.0583 0.034 Uiso 1 1 calc R . . C40 C 0.83874(17) 0.61569(17) 0.13544(16) 0.0341(6) Uani 1 1 d . . . H40 H 0.8356 0.6778 0.1260 0.041 Uiso 1 1 calc R . . C19 C 1.23274(15) 0.43480(16) 0.11658(17) 0.0302(6) Uani 1 1 d . . . H19A H 1.2385 0.4672 0.0654 0.036 Uiso 1 1 calc R . . H19B H 1.2475 0.4757 0.1632 0.036 Uiso 1 1 calc R . . C6 C 0.99028(16) -0.11386(19) -0.04281(16) 0.0344(6) Uani 1 1 d . . . H6A H 1.0132 -0.1492 -0.0860 0.041 Uiso 1 1 calc R . . H6B H 0.9785 -0.0531 -0.0642 0.041 Uiso 1 1 calc R . . C27 C 1.24836(16) -0.23120(17) 0.12647(15) 0.0295(6) Uani 1 1 d . . . H27 H 1.2992 -0.2203 0.1652 0.035 Uiso 1 1 calc R . . C34 C 0.66632(16) -0.08046(17) 0.12365(15) 0.0306(6) Uani 1 1 d . . . H34 H 0.6409 -0.0424 0.1601 0.037 Uiso 1 1 calc R . . C39 C 0.76806(17) 0.57281(17) 0.16228(15) 0.0322(6) Uani 1 1 d . . . H39 H 0.7168 0.6052 0.1720 0.039 Uiso 1 1 calc R . . C35 C 0.66163(14) 0.12915(16) 0.11653(15) 0.0272(5) Uani 1 1 d . . . H35A H 0.6339 0.1318 0.1674 0.033 Uiso 1 1 calc R . . H35B H 0.6308 0.0827 0.0811 0.033 Uiso 1 1 calc R . . C44 C 1.53341(16) 0.35875(18) 0.26994(16) 0.0345(6) Uani 1 1 d . . . H44 H 1.5896 0.3569 0.3030 0.041 Uiso 1 1 calc R . . C28 C 1.23383(18) -0.31602(17) 0.09368(16) 0.0356(6) Uani 1 1 d . . . H28 H 1.2739 -0.3630 0.1101 0.043 Uiso 1 1 calc R . . C29 C 1.15973(17) -0.33018(18) 0.03661(15) 0.0341(6) Uani 1 1 d . . . H29 H 1.1506 -0.3873 0.0127 0.041 Uiso 1 1 calc R . . C33 C 0.62313(18) -0.15897(18) 0.09882(17) 0.0381(7) Uani 1 1 d . . . H33 H 0.5692 -0.1745 0.1185 0.046 Uiso 1 1 calc R . . O7 O 1.07532(15) 0.21676(15) 0.24527(15) 0.0561(6) Uani 1 1 d . . . H1 H 1.116(3) 0.166(3) 0.236(3) 0.103(14) Uiso 1 1 d . . . H2 H 1.019(3) 0.196(3) 0.235(2) 0.088(13) Uiso 1 1 d . . . H1G H 0.503(3) 0.595(4) -0.046(3) 0.036(15) Uiso 0.50 1 d P . . 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 Cl2 0.0438(4) 0.0821(7) 0.0542(5) 0.0021(4) -0.0052(4) 0.0059(4) Cl1 0.0623(9) 0.0382(8) 0.0491(9) 0.0013(7) 0.0142(7) -0.0111(7) C1G 0.043(3) 0.042(4) 0.039(3) 0.002(3) 0.010(3) 0.002(3) O4 0.0192(8) 0.0298(10) 0.0460(11) 0.0007(8) -0.0009(8) 0.0001(7) O1 0.0231(9) 0.0315(10) 0.0448(11) -0.0064(8) 0.0123(8) -0.0026(7) O3 0.0313(9) 0.0310(10) 0.0321(9) -0.0042(8) 0.0037(8) 0.0092(8) O2 0.0218(8) 0.0396(11) 0.0354(10) -0.0066(8) -0.0010(8) 0.0011(8) O6 0.0277(9) 0.0238(10) 0.0577(12) -0.0121(9) -0.0104(9) 0.0029(7) O5 0.0235(8) 0.0215(9) 0.0499(11) -0.0026(8) 0.0084(8) -0.0054(7) C4 0.0267(12) 0.0268(14) 0.0230(12) 0.0003(10) 0.0076(10) -0.0052(10) C25 0.0188(11) 0.0279(14) 0.0321(13) -0.0022(11) 0.0062(10) 0.0011(10) C43 0.0264(13) 0.0322(15) 0.0372(15) -0.0084(12) 0.0050(12) -0.0076(11) C45 0.0275(13) 0.0335(15) 0.0319(14) -0.0032(11) 0.0008(11) 0.0012(11) C23 0.0204(11) 0.0267(13) 0.0209(12) -0.0008(10) 0.0006(9) -0.0014(10) C21 0.0253(12) 0.0259(14) 0.0277(13) -0.0062(10) 0.0090(11) -0.0041(10) C15 0.0246(12) 0.0271(13) 0.0209(12) -0.0045(10) -0.0008(10) -0.0025(10) C12 0.0180(11) 0.0291(14) 0.0254(12) 0.0021(10) 0.0083(10) -0.0007(10) C5 0.0271(12) 0.0315(15) 0.0264(13) -0.0047(11) 0.0116(11) -0.0104(11) C30 0.0275(13) 0.0365(16) 0.0322(14) -0.0027(12) 0.0076(11) -0.0046(11) C38 0.0274(12) 0.0339(15) 0.0269(13) -0.0047(11) 0.0003(11) 0.0015(11) C26 0.0222(12) 0.0256(13) 0.0333(14) -0.0033(11) 0.0023(11) 0.0009(10) C10 0.0223(11) 0.0306(14) 0.0212(12) 0.0035(10) 0.0033(10) -0.0001(10) C3 0.0233(12) 0.0274(14) 0.0219(12) 0.0004(10) 0.0039(10) -0.0012(10) C13 0.0225(12) 0.0267(13) 0.0229(12) -0.0008(10) 0.0080(10) 0.0023(10) C8 0.0236(12) 0.0290(14) 0.0307(13) 0.0065(11) -0.0030(11) 0.0076(10) C31 0.0390(15) 0.0240(14) 0.0357(15) -0.0048(11) -0.0074(12) 0.0108(11) C42 0.0303(13) 0.0254(14) 0.0374(14) -0.0033(11) 0.0056(12) -0.0028(11) C2 0.0233(12) 0.0244(13) 0.0209(12) 0.0017(10) 0.0017(10) -0.0010(10) C11 0.0208(11) 0.0249(13) 0.0232(12) 0.0020(10) 0.0065(10) -0.0010(10) C14 0.0214(11) 0.0289(14) 0.0231(12) -0.0013(10) 0.0047(10) 0.0014(10) C32 0.0339(14) 0.0281(15) 0.0524(18) 0.0046(13) -0.0068(13) -0.0035(12) C20 0.0193(12) 0.0308(14) 0.0311(13) -0.0073(11) 0.0018(11) -0.0012(10) C1 0.0221(12) 0.0247(13) 0.0236(12) 0.0014(10) 0.0009(10) 0.0000(10) C36 0.0197(12) 0.0306(15) 0.0374(15) 0.0005(11) -0.0016(11) 0.0010(10) C9 0.0286(12) 0.0246(13) 0.0219(12) 0.0028(10) -0.0023(10) 0.0022(10) C16 0.0228(12) 0.0263(14) 0.0281(13) -0.0045(10) -0.0016(10) 0.0012(10) C24 0.0193(11) 0.0304(14) 0.0324(13) -0.0015(11) 0.0031(10) -0.0026(10) C37 0.0210(12) 0.0292(15) 0.0401(15) -0.0001(11) 0.0029(11) 0.0021(10) C41 0.0299(13) 0.0249(14) 0.0322(14) -0.0014(11) -0.0008(11) -0.0046(11) C18 0.0288(13) 0.0230(13) 0.0427(15) -0.0003(11) 0.0071(12) -0.0027(10) C22 0.0216(12) 0.0331(15) 0.0268(13) -0.0044(11) 0.0037(10) -0.0015(10) C7 0.0296(13) 0.0374(16) 0.0353(15) -0.0066(12) 0.0009(12) 0.0060(11) C17 0.0242(12) 0.0261(13) 0.0356(14) -0.0024(11) 0.0046(11) -0.0063(10) C40 0.0389(15) 0.0244(14) 0.0356(14) -0.0029(11) -0.0075(12) 0.0025(12) C19 0.0242(12) 0.0195(13) 0.0456(16) -0.0041(11) 0.0004(11) 0.0019(10) C6 0.0352(14) 0.0398(16) 0.0278(13) -0.0032(12) 0.0030(12) -0.0006(12) C27 0.0315(13) 0.0309(15) 0.0263(13) 0.0021(11) 0.0042(11) -0.0051(11) C34 0.0332(13) 0.0311(15) 0.0266(13) 0.0048(11) 0.0001(11) -0.0025(11) C39 0.0297(13) 0.0323(15) 0.0327(14) -0.0091(11) -0.0028(11) 0.0070(11) C35 0.0198(11) 0.0291(14) 0.0335(13) -0.0002(11) 0.0064(10) -0.0017(10) C44 0.0241(13) 0.0429(17) 0.0345(14) -0.0092(12) -0.0032(11) -0.0059(12) C28 0.0474(16) 0.0242(14) 0.0375(15) 0.0080(12) 0.0137(13) 0.0003(12) C29 0.0450(16) 0.0293(15) 0.0301(14) -0.0047(11) 0.0130(13) -0.0175(12) C33 0.0373(14) 0.0312(16) 0.0442(16) 0.0066(13) 0.0002(13) -0.0050(12) O7 0.0308(11) 0.0477(14) 0.0863(17) -0.0198(12) -0.0047(11) -0.0021(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl2 C1G 1.718(6) 3_665 ? Cl2 C1G 1.733(6) . ? Cl1 C1G 1.758(6) . ? C1G Cl2 1.718(6) 3_665 ? C1G C1G 1.891(12) 3_665 ? O4 C12 1.231(3) . ? O1 C1 1.232(3) . ? O3 C8 1.369(3) . ? O3 C7 1.439(3) . ? O2 C5 1.358(3) . ? O2 C6 1.446(3) . ? O6 C20 1.371(3) . ? O6 C19 1.434(3) . ? O5 C16 1.367(3) . ? O5 C17 1.437(3) . ? C4 C27 1.386(3) . ? C4 C5 1.422(3) . ? C4 C3 1.459(3) . ? C25 C24 1.516(3) . ? C25 C26 1.527(3) . ? C43 C44 1.379(4) . ? C43 C42 1.386(3) . ? C45 C44 1.389(4) . ? C45 C21 1.392(3) . ? C23 C22 1.334(3) . ? C23 C1 1.497(3) . ? C23 C24 1.513(3) . ? C21 C20 1.401(3) . ? C21 C22 1.474(3) . ? C15 C38 1.391(3) . ? C15 C16 1.411(3) . ? C15 C14 1.471(3) . ? C12 C11 1.499(3) . ? C12 C13 1.500(3) . ? C5 C30 1.387(3) . ? C30 C29 1.372(4) . ? C38 C39 1.387(4) . ? C26 C2 1.517(3) . ? C10 C11 1.340(3) . ? C10 C9 1.473(3) . ? C3 C2 1.346(3) . ? C13 C14 1.352(3) . ? C13 C37 1.508(3) . ? C8 C31 1.403(4) . ? C8 C9 1.409(3) . ? C31 C32 1.369(4) . ? C42 C20 1.388(3) . ? C2 C1 1.491(3) . ? C11 C35 1.505(3) . ? C32 C33 1.372(4) . ? C36 C37 1.518(3) . ? C36 C35 1.519(3) . ? C9 C34 1.401(3) . ? C16 C41 1.398(3) . ? C41 C40 1.384(4) . ? C18 C17 1.503(3) . ? C18 C19 1.506(3) . ? C7 C6 1.484(4) . ? C40 C39 1.376(4) . ? C27 C28 1.395(4) . ? C34 C33 1.389(4) . ? C28 C29 1.385(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1G Cl2 C1G 66.4(3) 3_665 . ? Cl2 C1G Cl2 113.6(3) 3_665 . ? Cl2 C1G Cl1 110.3(3) 3_665 . ? Cl2 C1G Cl1 109.1(3) . . ? Cl2 C1G C1G 57.2(3) 3_665 3_665 ? Cl2 C1G C1G 56.4(3) . 3_665 ? Cl1 C1G C1G 128.0(5) . 3_665 ? C8 O3 C7 115.89(19) . . ? C5 O2 C6 119.94(19) . . ? C20 O6 C19 119.32(18) . . ? C16 O5 C17 118.21(18) . . ? C27 C4 C5 119.1(2) . . ? C27 C4 C3 121.9(2) . . ? C5 C4 C3 119.0(2) . . ? C24 C25 C26 110.3(2) . . ? C44 C43 C42 120.3(2) . . ? C44 C45 C21 120.5(2) . . ? C22 C23 C1 116.1(2) . . ? C22 C23 C24 124.5(2) . . ? C1 C23 C24 119.1(2) . . ? C45 C21 C20 118.2(2) . . ? C45 C21 C22 123.5(2) . . ? C20 C21 C22 117.9(2) . . ? C38 C15 C16 117.2(2) . . ? C38 C15 C14 124.7(2) . . ? C16 C15 C14 118.1(2) . . ? O4 C12 C11 119.9(2) . . ? O4 C12 C13 121.2(2) . . ? C11 C12 C13 118.92(19) . . ? O2 C5 C30 124.8(2) . . ? O2 C5 C4 115.6(2) . . ? C30 C5 C4 119.6(2) . . ? C29 C30 C5 119.7(2) . . ? C39 C38 C15 122.1(2) . . ? C2 C26 C25 111.23(19) . . ? C11 C10 C9 127.5(2) . . ? C2 C3 C4 127.6(2) . . ? C14 C13 C12 116.7(2) . . ? C14 C13 C37 124.1(2) . . ? C12 C13 C37 119.0(2) . . ? O3 C8 C31 124.6(2) . . ? O3 C8 C9 115.1(2) . . ? C31 C8 C9 120.3(2) . . ? C32 C31 C8 120.2(3) . . ? C43 C42 C20 119.2(2) . . ? C3 C2 C1 116.0(2) . . ? C3 C2 C26 125.6(2) . . ? C1 C2 C26 118.25(19) . . ? C10 C11 C12 117.5(2) . . ? C10 C11 C35 125.2(2) . . ? C12 C11 C35 117.3(2) . . ? C13 C14 C15 128.4(2) . . ? C31 C32 C33 120.9(3) . . ? O6 C20 C42 124.3(2) . . ? O6 C20 C21 114.3(2) . . ? C42 C20 C21 121.3(2) . . ? O1 C1 C2 120.4(2) . . ? O1 C1 C23 120.5(2) . . ? C2 C1 C23 119.12(19) . . ? C37 C36 C35 111.1(2) . . ? C34 C9 C8 117.2(2) . . ? C34 C9 C10 122.4(2) . . ? C8 C9 C10 120.3(2) . . ? O5 C16 C41 123.4(2) . . ? O5 C16 C15 115.4(2) . . ? C41 C16 C15 121.2(2) . . ? C23 C24 C25 111.23(18) . . ? C13 C37 C36 113.2(2) . . ? C40 C41 C16 119.2(2) . . ? C17 C18 C19 112.8(2) . . ? C23 C22 C21 129.1(2) . . ? O3 C7 C6 107.5(2) . . ? O5 C17 C18 105.91(19) . . ? C39 C40 C41 120.9(2) . . ? O6 C19 C18 105.68(19) . . ? O2 C6 C7 113.6(2) . . ? C4 C27 C28 120.9(2) . . ? C33 C34 C9 121.8(3) . . ? C40 C39 C38 119.5(2) . . ? C11 C35 C36 110.59(19) . . ? C43 C44 C45 120.4(2) . . ? C29 C28 C27 118.6(2) . . ? C30 C29 C28 122.1(2) . . ? C32 C33 C34 119.5(3) . . ? 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 C1G Cl2 C1G Cl2 0.0 3_665 . . 3_665 ? C1G Cl2 C1G Cl1 123.5(5) 3_665 . . . ? C44 C45 C21 C20 1.9(4) . . . . ? C44 C45 C21 C22 -170.7(2) . . . . ? C6 O2 C5 C30 -13.3(3) . . . . ? C6 O2 C5 C4 165.0(2) . . . . ? C27 C4 C5 O2 179.4(2) . . . . ? C3 C4 C5 O2 0.6(3) . . . . ? C27 C4 C5 C30 -2.2(3) . . . . ? C3 C4 C5 C30 179.1(2) . . . . ? O2 C5 C30 C29 179.2(2) . . . . ? C4 C5 C30 C29 0.9(4) . . . . ? C16 C15 C38 C39 1.8(3) . . . . ? C14 C15 C38 C39 179.8(2) . . . . ? C24 C25 C26 C2 60.0(3) . . . . ? C27 C4 C3 C2 39.7(4) . . . . ? C5 C4 C3 C2 -141.6(2) . . . . ? O4 C12 C13 C14 12.9(3) . . . . ? C11 C12 C13 C14 -166.2(2) . . . . ? O4 C12 C13 C37 -171.8(2) . . . . ? C11 C12 C13 C37 9.1(3) . . . . ? C7 O3 C8 C31 -6.4(3) . . . . ? C7 O3 C8 C9 174.40(19) . . . . ? O3 C8 C31 C32 178.9(2) . . . . ? C9 C8 C31 C32 -2.0(4) . . . . ? C44 C43 C42 C20 0.7(4) . . . . ? C4 C3 C2 C1 179.9(2) . . . . ? C4 C3 C2 C26 5.3(4) . . . . ? C25 C26 C2 C3 139.8(2) . . . . ? C25 C26 C2 C1 -34.7(3) . . . . ? C9 C10 C11 C12 175.8(2) . . . . ? C9 C10 C11 C35 -7.7(4) . . . . ? O4 C12 C11 C10 -19.7(3) . . . . ? C13 C12 C11 C10 159.4(2) . . . . ? O4 C12 C11 C35 163.6(2) . . . . ? C13 C12 C11 C35 -17.3(3) . . . . ? C12 C13 C14 C15 174.1(2) . . . . ? C37 C13 C14 C15 -0.9(4) . . . . ? C38 C15 C14 C13 37.2(4) . . . . ? C16 C15 C14 C13 -144.8(2) . . . . ? C8 C31 C32 C33 -0.4(4) . . . . ? C19 O6 C20 C42 -31.7(4) . . . . ? C19 O6 C20 C21 150.1(2) . . . . ? C43 C42 C20 O6 -177.8(2) . . . . ? C43 C42 C20 C21 0.3(4) . . . . ? C45 C21 C20 O6 176.7(2) . . . . ? C22 C21 C20 O6 -10.3(3) . . . . ? C45 C21 C20 C42 -1.6(4) . . . . ? C22 C21 C20 C42 171.4(2) . . . . ? C3 C2 C1 O1 12.6(3) . . . . ? C26 C2 C1 O1 -172.4(2) . . . . ? C3 C2 C1 C23 -166.1(2) . . . . ? C26 C2 C1 C23 8.9(3) . . . . ? C22 C23 C1 O1 -12.1(3) . . . . ? C24 C23 C1 O1 173.5(2) . . . . ? C22 C23 C1 C2 166.6(2) . . . . ? C24 C23 C1 C2 -7.8(3) . . . . ? O3 C8 C9 C34 -177.8(2) . . . . ? C31 C8 C9 C34 3.0(3) . . . . ? O3 C8 C9 C10 -0.7(3) . . . . ? C31 C8 C9 C10 -179.9(2) . . . . ? C11 C10 C9 C34 -38.2(4) . . . . ? C11 C10 C9 C8 144.9(2) . . . . ? C17 O5 C16 C41 13.2(3) . . . . ? C17 O5 C16 C15 -168.5(2) . . . . ? C38 C15 C16 O5 179.6(2) . . . . ? C14 C15 C16 O5 1.5(3) . . . . ? C38 C15 C16 C41 -2.1(3) . . . . ? C14 C15 C16 C41 179.8(2) . . . . ? C22 C23 C24 C25 -141.3(2) . . . . ? C1 C23 C24 C25 32.6(3) . . . . ? C26 C25 C24 C23 -58.7(3) . . . . ? C14 C13 C37 C36 147.8(2) . . . . ? C12 C13 C37 C36 -27.1(3) . . . . ? C35 C36 C37 C13 53.2(3) . . . . ? O5 C16 C41 C40 179.1(2) . . . . ? C15 C16 C41 C40 1.0(4) . . . . ? C1 C23 C22 C21 178.9(2) . . . . ? C24 C23 C22 C21 -7.0(4) . . . . ? C45 C21 C22 C23 -48.7(4) . . . . ? C20 C21 C22 C23 138.7(3) . . . . ? C8 O3 C7 C6 -179.61(19) . . . . ? C16 O5 C17 C18 169.7(2) . . . . ? C19 C18 C17 O5 -171.7(2) . . . . ? C16 C41 C40 C39 0.6(4) . . . . ? C20 O6 C19 C18 -140.9(2) . . . . ? C17 C18 C19 O6 176.7(2) . . . . ? C5 O2 C6 C7 87.2(3) . . . . ? O3 C7 C6 O2 72.6(3) . . . . ? C5 C4 C27 C28 1.4(4) . . . . ? C3 C4 C27 C28 -179.9(2) . . . . ? C8 C9 C34 C33 -1.8(3) . . . . ? C10 C9 C34 C33 -178.8(2) . . . . ? C41 C40 C39 C38 -0.9(4) . . . . ? C15 C38 C39 C40 -0.3(4) . . . . ? C10 C11 C35 C36 -133.6(2) . . . . ? C12 C11 C35 C36 42.8(3) . . . . ? C37 C36 C35 C11 -60.9(3) . . . . ? C42 C43 C44 C45 -0.5(4) . . . . ? C21 C45 C44 C43 -0.9(4) . . . . ? C4 C27 C28 C29 0.7(4) . . . . ? C5 C30 C29 C28 1.3(4) . . . . ? C27 C28 C29 C30 -2.1(4) . . . . ? C31 C32 C33 C34 1.7(4) . . . . ? C9 C34 C33 C32 -0.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.20 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.650 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.060 _exptl_crystal_recrystallization_method 'slow evaporation from CHCl3 solution' # Attachment 'HCM 46.CHCl3.CIF' data_46_CHCl3 _database_code_depnum_ccdc_archive 'CCDC 630663' _audit_creation_method SHELXL-97 _chemical_name_systematic ;3,4:9,10:18,19:27,28-Tetrabenzo-5,8,20,23,26-pentaoxatricyclo[28.3.1.1(12,16)]- pentatriaconta-1(34),3,9,12,14,16(35),18,27,30,32-decaene-34,35-diol chloroform solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C46 H44 O7)2 (C H Cl3)2' _chemical_formula_sum 'C94 H90 Cl6 O14' _chemical_formula_weight 1656.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1150(3) _cell_length_b 22.3638(5) _cell_length_c 30.8380(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.3770(10) _cell_angle_gamma 90.00 _cell_volume 8348.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3472 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9605 _exptl_absorpt_correction_T_max 0.9734 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 85438 _diffrn_reflns_av_R_equivalents 0.1973 _diffrn_reflns_av_sigmaI/netI 0.3025 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.96 _reflns_number_total 19746 _reflns_number_gt 6972 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement 'Nonius collect' _computing_data_reduction 'Nonius collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material ciftab _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The two ASU chloroform molecules were highly disordered. One CHCl3 was modelled over two positions with site occupancy factors of 50% each. The other CHCl3 was modelled over three positions with site occupancy factors of 20, 40, and 40%. A common bond length restraint was applied to all C-Cl bond lengths and allowed to refine as a single free variable. A common bond length restraint was applied to two Cl..Cl distances. ; _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^)+(0.0779P)^2^+0.6859P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 19746 _refine_ls_number_parameters 1028 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.2959 _refine_ls_R_factor_gt 0.0939 _refine_ls_wR_factor_ref 0.2157 _refine_ls_wR_factor_gt 0.1596 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8200(2) 0.86934(12) 0.20415(9) 0.0270(7) Uani 1 1 d . . . H1O H 0.8275 0.8564 0.2297 0.032 Uiso 1 1 calc R . . C1 C 0.8847(3) 0.91959(17) 0.19968(15) 0.0205(10) Uani 1 1 d . . . O2 O 0.7794(2) 0.83657(13) 0.28944(10) 0.0356(8) Uani 1 1 d . . . C2 C 0.9506(3) 0.94278(18) 0.23350(14) 0.0193(10) Uani 1 1 d . . . O3 O 0.7822(2) 0.72806(12) 0.24762(9) 0.0267(7) Uani 1 1 d . . . C3 C 0.9537(3) 0.91565(17) 0.27856(14) 0.0229(11) Uani 1 1 d . . . H3A H 0.9586 0.8716 0.2758 0.028 Uiso 1 1 calc R . . H3B H 1.0215 0.9295 0.2945 0.028 Uiso 1 1 calc R . . O4 O 0.5606(2) 0.78772(12) 0.11958(9) 0.0279(8) Uani 1 1 d . . . H4O H 0.5022 0.8017 0.1079 0.033 Uiso 1 1 calc R . . C4 C 0.8560(3) 0.93059(18) 0.30485(13) 0.0209(10) Uani 1 1 d . . . O5 O 0.3681(2) 0.85750(13) 0.11878(10) 0.0346(8) Uani 1 1 d . . . C5 C 0.7705(3) 0.89055(19) 0.31069(14) 0.0240(11) Uani 1 1 d . . . O6 O 0.4418(2) 0.91137(13) 0.04383(10) 0.0345(8) Uani 1 1 d . . . C6 C 0.7402(4) 0.78346(19) 0.31050(14) 0.0302(12) Uani 1 1 d . . . H6A H 0.6604 0.7775 0.3036 0.036 Uiso 1 1 calc R . . H6B H 0.7519 0.7867 0.3424 0.036 Uiso 1 1 calc R . . O7 O 0.6844(2) 0.88719(12) 0.05172(9) 0.0274(7) Uani 1 1 d . . . C7 C 0.8058(4) 0.7326(2) 0.29331(14) 0.0322(12) Uani 1 1 d . . . H7A H 0.8857 0.7397 0.2991 0.039 Uiso 1 1 calc R . . H7B H 0.7856 0.6949 0.3078 0.039 Uiso 1 1 calc R . . C8 C 0.8520(3) 0.69446(19) 0.22355(15) 0.0236(11) Uani 1 1 d . . . C9 C 0.8347(3) 0.69766(18) 0.17829(14) 0.0203(10) Uani 1 1 d . . . C10 C 0.7419(3) 0.73385(17) 0.15765(14) 0.0207(10) Uani 1 1 d . . . H10A H 0.7634 0.7467 0.1285 0.025 Uiso 1 1 calc R . . H10B H 0.7317 0.7703 0.1752 0.025 Uiso 1 1 calc R . . C11 C 0.6320(3) 0.70092(18) 0.15315(13) 0.0197(10) Uani 1 1 d . . . C12 C 0.5412(3) 0.73028(19) 0.13396(14) 0.0218(11) Uani 1 1 d . . . C13 C 0.4381(3) 0.70325(19) 0.12863(14) 0.0245(11) Uani 1 1 d . . . C14 C 0.3380(3) 0.7350(2) 0.10823(14) 0.0293(12) Uani 1 1 d . . . H14A H 0.3630 0.7618 0.0850 0.035 Uiso 1 1 calc R . . H14B H 0.2883 0.7048 0.0945 0.035 Uiso 1 1 calc R . . C15 C 0.2730(3) 0.7715(2) 0.13984(14) 0.0275(11) Uani 1 1 d . . . C16 C 0.2863(3) 0.8335(2) 0.14362(15) 0.0262(11) Uani 1 1 d . . . C17 C 0.3776(3) 0.92157(19) 0.11551(15) 0.0314(12) Uani 1 1 d . . . H17A H 0.3938 0.9392 0.1445 0.038 Uiso 1 1 calc R . . H17B H 0.3076 0.9389 0.1035 0.038 Uiso 1 1 calc R . . C18 C 0.4701(4) 0.9346(2) 0.08599(15) 0.0312(12) Uani 1 1 d . . . H18A H 0.4823 0.9782 0.0843 0.037 Uiso 1 1 calc R . . H18B H 0.5392 0.9157 0.0975 0.037 Uiso 1 1 calc R . . C19 C 0.5235(4) 0.9196(2) 0.01274(15) 0.0363(13) Uani 1 1 d . . . H19A H 0.5570 0.9596 0.0170 0.044 Uiso 1 1 calc R . . H19B H 0.4873 0.9187 -0.0166 0.044 Uiso 1 1 calc R . . C20 C 0.6140(3) 0.87360(19) 0.01477(14) 0.0284(11) Uani 1 1 d . . . H20A H 0.5823 0.8330 0.0176 0.034 Uiso 1 1 calc R . . H20B H 0.6563 0.8750 -0.0120 0.034 Uiso 1 1 calc R . . C21 C 0.7758(3) 0.85189(19) 0.06023(14) 0.0207(10) Uani 1 1 d . . . C22 C 0.8406(3) 0.86889(18) 0.09674(13) 0.0193(10) Uani 1 1 d . . . C23 C 0.8023(3) 0.92202(18) 0.12256(13) 0.0233(11) Uani 1 1 d . . . H23A H 0.7865 0.9553 0.1021 0.028 Uiso 1 1 calc R . . H23B H 0.7319 0.9112 0.1357 0.028 Uiso 1 1 calc R . . C24 C 0.8805(3) 0.94455(18) 0.15806(14) 0.0205(10) Uani 1 1 d . . . C25 C 0.9495(3) 0.99336(18) 0.15099(14) 0.0228(11) Uani 1 1 d . . . H25 H 0.9507 1.0103 0.1228 0.027 Uiso 1 1 calc R . . C26 C 1.0161(3) 1.01766(18) 0.18403(15) 0.0241(11) Uani 1 1 d . . . H26 H 1.0619 1.0511 0.1786 0.029 Uiso 1 1 calc R . . C27 C 1.0149(3) 0.99258(18) 0.22513(14) 0.0223(11) Uani 1 1 d . . . H27 H 1.0591 1.0098 0.2480 0.027 Uiso 1 1 calc R . . C28 C 0.8497(4) 0.9852(2) 0.32536(16) 0.0416(14) Uani 1 1 d . . . H28 H 0.9082 1.0131 0.3226 0.050 Uiso 1 1 calc R . . C29 C 0.7614(5) 1.0004(2) 0.34959(18) 0.0572(17) Uani 1 1 d . . . H29 H 0.7590 1.0385 0.3632 0.069 Uiso 1 1 calc R . . C30 C 0.6769(4) 0.9607(3) 0.35416(17) 0.0507(16) Uani 1 1 d . . . H30 H 0.6157 0.9714 0.3708 0.061 Uiso 1 1 calc R . . C31 C 0.6800(4) 0.9051(2) 0.33468(15) 0.0357(13) Uani 1 1 d . . . H31 H 0.6214 0.8775 0.3377 0.043 Uiso 1 1 calc R . . C32 C 0.9366(4) 0.65928(19) 0.24149(15) 0.0300(12) Uani 1 1 d . . . H32 H 0.9477 0.6571 0.2721 0.036 Uiso 1 1 calc R . . C33 C 1.0048(4) 0.62750(18) 0.21516(16) 0.0312(12) Uani 1 1 d . . . H33 H 1.0627 0.6037 0.2277 0.037 Uiso 1 1 calc R . . C34 C 0.9888(4) 0.63031(18) 0.17084(16) 0.0286(12) Uani 1 1 d . . . H34 H 1.0353 0.6083 0.1526 0.034 Uiso 1 1 calc R . . C35 C 0.9050(3) 0.66534(18) 0.15299(15) 0.0245(11) Uani 1 1 d . . . H35 H 0.8953 0.6673 0.1223 0.029 Uiso 1 1 calc R . . C36 C 0.6181(3) 0.64272(19) 0.16697(14) 0.0256(11) Uani 1 1 d . . . H36 H 0.6793 0.6219 0.1799 0.031 Uiso 1 1 calc R . . C37 C 0.5158(4) 0.6139(2) 0.16223(16) 0.0361(13) Uani 1 1 d . . . H37 H 0.5072 0.5738 0.1717 0.043 Uiso 1 1 calc R . . C38 C 0.4280(4) 0.6447(2) 0.14354(15) 0.0331(12) Uani 1 1 d . . . H38 H 0.3581 0.6255 0.1407 0.040 Uiso 1 1 calc R . . C39 C 0.1964(3) 0.7447(2) 0.16564(15) 0.0311(12) Uani 1 1 d . . . H39 H 0.1867 0.7026 0.1639 0.037 Uiso 1 1 calc R . . C40 C 0.1338(3) 0.7770(2) 0.19376(15) 0.0353(13) Uani 1 1 d . . . H40 H 0.0817 0.7574 0.2111 0.042 Uiso 1 1 calc R . . C41 C 0.1478(3) 0.8379(2) 0.19637(15) 0.0320(12) Uani 1 1 d . . . H41 H 0.1046 0.8604 0.2155 0.038 Uiso 1 1 calc R . . C42 C 0.2243(3) 0.8671(2) 0.17142(15) 0.0288(12) Uani 1 1 d . . . H42 H 0.2338 0.9092 0.1734 0.035 Uiso 1 1 calc R . . C43 C 0.8046(3) 0.80322(19) 0.03530(14) 0.0259(11) Uani 1 1 d . . . H43 H 0.7608 0.7923 0.0103 0.031 Uiso 1 1 calc R . . C44 C 0.8987(3) 0.77047(19) 0.04740(14) 0.0268(11) Uani 1 1 d . . . H44 H 0.9179 0.7365 0.0308 0.032 Uiso 1 1 calc R . . C45 C 0.9641(3) 0.78666(18) 0.08302(14) 0.0238(11) Uani 1 1 d . . . H45 H 1.0292 0.7647 0.0907 0.029 Uiso 1 1 calc R . . C46 C 0.9337(3) 0.83570(18) 0.10775(14) 0.0222(11) Uani 1 1 d . . . H46 H 0.9780 0.8465 0.1327 0.027 Uiso 1 1 calc R . . O1' O 0.4161(2) 0.86102(12) 0.34085(9) 0.0281(8) Uani 1 1 d . . . H1O' H 0.4046 0.8532 0.3144 0.034 Uiso 1 1 calc R . . C1' C 0.3571(4) 0.91138(18) 0.35144(15) 0.0244(11) Uani 1 1 d . . . O2' O 0.4427(2) 0.84226(12) 0.25220(9) 0.0244(7) Uani 1 1 d . . . C2' C 0.2900(3) 0.94288(18) 0.32166(14) 0.0241(11) Uani 1 1 d . . . O3' O 0.4598(2) 0.72774(12) 0.28905(9) 0.0246(7) Uani 1 1 d . . . C3' C 0.2861(3) 0.92683(18) 0.27423(14) 0.0241(11) Uani 1 1 d . . . H3C H 0.2226 0.9475 0.2597 0.029 Uiso 1 1 calc R . . H3D H 0.2733 0.8833 0.2713 0.029 Uiso 1 1 calc R . . O4' O 0.6923(2) 0.75371(12) 0.42155(9) 0.0284(8) Uani 1 1 d . . . H4O' H 0.7513 0.7652 0.4342 0.034 Uiso 1 1 calc R . . C4' C 0.3895(3) 0.94286(19) 0.25128(13) 0.0214(10) Uani 1 1 d . . . O5' O 0.8853(2) 0.81854(13) 0.42434(10) 0.0380(9) Uani 1 1 d . . . C5' C 0.4663(3) 0.90022(19) 0.23951(13) 0.0217(11) Uani 1 1 d . . . O6' O 0.8075(3) 0.86316(13) 0.50039(11) 0.0409(9) Uani 1 1 d . . . C6' C 0.4972(3) 0.79425(18) 0.23144(14) 0.0249(11) Uani 1 1 d . . . H6C H 0.5759 0.7925 0.2414 0.030 Uiso 1 1 calc R . . H6D H 0.4931 0.7996 0.1995 0.030 Uiso 1 1 calc R . . O7' O 0.5630(3) 0.85367(13) 0.49492(10) 0.0348(8) Uani 1 1 d . . . C7' C 0.4387(4) 0.73829(19) 0.24377(14) 0.0284(11) Uani 1 1 d . . . H7C H 0.3583 0.7426 0.2375 0.034 Uiso 1 1 calc R . . H7D H 0.4655 0.7041 0.2267 0.034 Uiso 1 1 calc R . . C8' C 0.3965(3) 0.68492(18) 0.30864(15) 0.0216(11) Uani 1 1 d . . . C9' C 0.4164(3) 0.67702(17) 0.35311(15) 0.0203(10) Uani 1 1 d . . . C10' C 0.5082(3) 0.70897(17) 0.37835(13) 0.0212(10) Uani 1 1 d . . . H10C H 0.4838 0.7173 0.4080 0.025 Uiso 1 1 calc R . . H10D H 0.5221 0.7478 0.3642 0.025 Uiso 1 1 calc R . . C11' C 0.6160(3) 0.67360(18) 0.38162(13) 0.0191(10) Uani 1 1 d . . . C12' C 0.7082(3) 0.69835(18) 0.40345(13) 0.0175(10) Uani 1 1 d . . . C13' C 0.8094(3) 0.66897(19) 0.40698(13) 0.0217(11) Uani 1 1 d . . . C14' C 0.9132(3) 0.69619(19) 0.42882(14) 0.0273(11) Uani 1 1 d . . . H14C H 0.8916 0.7205 0.4539 0.033 Uiso 1 1 calc R . . H14D H 0.9616 0.6635 0.4400 0.033 Uiso 1 1 calc R . . C15' C 0.9781(3) 0.7353(2) 0.39859(14) 0.0233(11) Uani 1 1 d . . . C16' C 0.9659(3) 0.7968(2) 0.39777(16) 0.0312(12) Uani 1 1 d . . . C17' C 0.8774(4) 0.88230(19) 0.43159(16) 0.0351(13) Uani 1 1 d . . . H17C H 0.8645 0.9036 0.4037 0.042 Uiso 1 1 calc R . . H17D H 0.9465 0.8976 0.4458 0.042 Uiso 1 1 calc R . . C18' C 0.7827(4) 0.8915(2) 0.46004(15) 0.0368(13) Uani 1 1 d . . . H18C H 0.7703 0.9348 0.4645 0.044 Uiso 1 1 calc R . . H18D H 0.7147 0.8741 0.4463 0.044 Uiso 1 1 calc R . . C19' C 0.7313(4) 0.8746(2) 0.53298(16) 0.0434(14) Uani 1 1 d . . . H19C H 0.7069 0.9168 0.5305 0.052 Uiso 1 1 calc R . . H19D H 0.7697 0.8697 0.5617 0.052 Uiso 1 1 calc R . . C20' C 0.6313(4) 0.8352(2) 0.53103(16) 0.0432(14) Uani 1 1 d . . . H20C H 0.6534 0.7929 0.5276 0.052 Uiso 1 1 calc R . . H20D H 0.5908 0.8389 0.5581 0.052 Uiso 1 1 calc R . . C21' C 0.4706(4) 0.8202(2) 0.48337(15) 0.0305(12) Uani 1 1 d . . . C22' C 0.4088(4) 0.8425(2) 0.44784(14) 0.0304(12) Uani 1 1 d . . . C23' C 0.4501(4) 0.8984(2) 0.42577(15) 0.0392(13) Uani 1 1 d . . . H11A H 0.4738 0.9274 0.4486 0.047 Uiso 1 1 calc R . . H11B H 0.5164 0.8875 0.4097 0.047 Uiso 1 1 calc R . . C24' C 0.3693(4) 0.9293(2) 0.39464(16) 0.0346(12) Uani 1 1 d . . . C25' C 0.3093(5) 0.9779(2) 0.40797(17) 0.0578(17) Uani 1 1 d . . . H25' H 0.3163 0.9907 0.4373 0.069 Uiso 1 1 calc R . . C26' C 0.2390(5) 1.0085(2) 0.37914(17) 0.0548(16) Uani 1 1 d . . . H26' H 0.1965 1.0412 0.3889 0.066 Uiso 1 1 calc R . . C27' C 0.2313(4) 0.9912(2) 0.33645(16) 0.0363(13) Uani 1 1 d . . . H27' H 0.1845 1.0129 0.3166 0.044 Uiso 1 1 calc R . . C28' C 0.4139(4) 1.0023(2) 0.24124(14) 0.0320(12) Uani 1 1 d . . . H28' H 0.3631 1.0327 0.2484 0.038 Uiso 1 1 calc R . . C29' C 0.5094(4) 1.0182(2) 0.22122(16) 0.0366(13) Uani 1 1 d . . . H29' H 0.5251 1.0590 0.2156 0.044 Uiso 1 1 calc R . . C30' C 0.5813(4) 0.9744(2) 0.20953(16) 0.0403(14) Uani 1 1 d . . . H30' H 0.6461 0.9851 0.1950 0.048 Uiso 1 1 calc R . . C31' C 0.5616(4) 0.9147(2) 0.21840(14) 0.0308(12) Uani 1 1 d . . . H31' H 0.6119 0.8845 0.2102 0.037 Uiso 1 1 calc R . . C32' C 0.3176(3) 0.65069(19) 0.28574(15) 0.0273(11) Uani 1 1 d . . . H32' H 0.3054 0.6560 0.2553 0.033 Uiso 1 1 calc R . . C33' C 0.2569(4) 0.60878(19) 0.30794(17) 0.0313(12) Uani 1 1 d . . . H33' H 0.2028 0.5854 0.2925 0.038 Uiso 1 1 calc R . . C34' C 0.2738(3) 0.60067(19) 0.35136(17) 0.0312(12) Uani 1 1 d . . . H34' H 0.2318 0.5719 0.3663 0.037 Uiso 1 1 calc R . . C35' C 0.3538(3) 0.63505(18) 0.37393(15) 0.0270(11) Uani 1 1 d . . . H35' H 0.3653 0.6294 0.4043 0.032 Uiso 1 1 calc R . . C36' C 0.6265(3) 0.61714(19) 0.36348(15) 0.0283(12) Uani 1 1 d . . . H36' H 0.5646 0.5994 0.3486 0.034 Uiso 1 1 calc R . . C37' C 0.7257(4) 0.5863(2) 0.36673(15) 0.0325(12) Uani 1 1 d . . . H37' H 0.7319 0.5477 0.3541 0.039 Uiso 1 1 calc R . . C38' C 0.8157(4) 0.61223(19) 0.38852(15) 0.0292(12) Uani 1 1 d . . . H38' H 0.8835 0.5909 0.3910 0.035 Uiso 1 1 calc R . . C39' C 1.0539(3) 0.7096(2) 0.37163(15) 0.0293(12) Uani 1 1 d . . . H39' H 1.0629 0.6674 0.3714 0.035 Uiso 1 1 calc R . . C40' C 1.1170(4) 0.7451(2) 0.34479(16) 0.0358(13) Uani 1 1 d . . . H40' H 1.1687 0.7271 0.3264 0.043 Uiso 1 1 calc R . . C41' C 1.1037(4) 0.8058(2) 0.34520(17) 0.0388(13) Uani 1 1 d . . . H41' H 1.1462 0.8300 0.3268 0.047 Uiso 1 1 calc R . . C42' C 1.0294(3) 0.8325(2) 0.37190(16) 0.0339(13) Uani 1 1 d . . . H42' H 1.0219 0.8747 0.3725 0.041 Uiso 1 1 calc R . . C43' C 0.4388(4) 0.7689(2) 0.50461(15) 0.0370(13) Uani 1 1 d . . . H43' H 0.4812 0.7546 0.5290 0.044 Uiso 1 1 calc R . . C44' C 0.3450(4) 0.7388(2) 0.49006(17) 0.0427(14) Uani 1 1 d . . . H44' H 0.3236 0.7033 0.5043 0.051 Uiso 1 1 calc R . . C45' C 0.2825(4) 0.7597(2) 0.45519(16) 0.0381(13) Uani 1 1 d . . . H45' H 0.2177 0.7390 0.4454 0.046 Uiso 1 1 calc R . . C46' C 0.3148(4) 0.8115(2) 0.43428(16) 0.0363(13) Uani 1 1 d . . . H46' H 0.2713 0.8259 0.4101 0.044 Uiso 1 1 calc R . . Cl2A Cl 0.1029(4) 0.8593(2) 0.55184(19) 0.0446(13) Uiso 0.40 1 d PD A 3 Cl3A Cl 0.1115(3) 0.96602(18) 0.49639(15) 0.0418(11) Uiso 0.40 1 d PD A 3 Cl4A Cl 0.1808(3) 0.92732(18) -0.04495(13) 0.0570(12) Uiso 0.50 1 d P B 1 Cl5A Cl 0.1072(2) 0.88977(14) 0.03810(10) 0.0448(8) Uiso 0.50 1 d P B 1 Cl6A Cl 0.1814(3) 1.01146(15) 0.02484(13) 0.0727(11) Uiso 0.50 1 d PD B 1 Cl2C Cl 0.1172(4) 0.8750(2) 0.56273(16) 0.0661(19) Uiso 0.40 1 d PD C 4 Cl3C Cl 0.1462(3) 0.94142(18) 0.48232(13) 0.0575(11) Uiso 0.40 1 d PD C 4 Cl4B Cl 0.1741(4) 0.90723(19) -0.03971(14) 0.0723(15) Uiso 0.50 1 d P B 2 Cl5B Cl 0.0948(3) 0.91653(15) 0.04770(11) 0.0601(10) Uiso 0.50 1 d P B 2 Cl6B Cl 0.1522(3) 1.02153(15) 0.00363(13) 0.0700(11) Uiso 0.50 1 d PD B 2 Cl2B Cl 0.1104(6) 0.8442(3) 0.5332(3) 0.065(3) Uiso 0.20 1 d PD D 5 Cl3B Cl 0.0853(5) 0.9647(3) 0.5102(3) 0.041(2) Uiso 0.20 1 d PD E 5 C1GC C 0.2083(7) 0.8947(5) 0.5216(3) 0.034(4) Uiso 0.40 1 d PD C 4 H1GC H 0.2334 0.8574 0.5072 0.041 Uiso 0.40 1 calc PR C 4 C1GA C 0.1803(6) 0.9034(3) 0.5153(3) 0.059(4) Uiso 0.60 1 d PD A 3 H1GA H 0.1968 0.8778 0.4897 0.071 Uiso 0.60 1 calc PR A 3 C2G C 0.1904(4) 0.94124(19) 0.01062(15) 0.0434(14) Uani 1 1 d D . . H2G H 0.2678 0.9297 0.0195 0.052 Uiso 1 1 calc R B 1 Cl1C Cl 0.3252(4) 0.9337(2) 0.54226(17) 0.0492(18) Uiso 0.40 1 d PD C 4 Cl1A Cl 0.3060(3) 0.92071(15) 0.54270(11) 0.0505(12) Uiso 0.60 1 d PD A 3 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 0.0296(17) 0.0287(18) 0.0226(18) 0.0020(14) 0.0001(14) -0.0094(15) C1 0.015(2) 0.013(2) 0.034(3) -0.001(2) 0.004(2) -0.001(2) O2 0.052(2) 0.0286(19) 0.027(2) -0.0065(16) 0.0137(16) -0.0174(17) C2 0.018(2) 0.017(2) 0.022(3) -0.001(2) 0.001(2) 0.000(2) O3 0.0278(17) 0.0359(19) 0.0164(18) -0.0005(15) 0.0000(14) -0.0033(15) C3 0.018(2) 0.018(2) 0.032(3) -0.003(2) -0.002(2) -0.006(2) O4 0.0221(17) 0.0279(18) 0.033(2) 0.0089(15) -0.0028(14) 0.0030(14) C4 0.022(2) 0.019(3) 0.021(3) -0.002(2) 0.002(2) 0.000(2) O5 0.0253(18) 0.033(2) 0.046(2) -0.0020(17) 0.0060(16) 0.0079(15) C5 0.026(3) 0.028(3) 0.019(3) -0.002(2) 0.000(2) 0.002(2) O6 0.0298(18) 0.048(2) 0.025(2) -0.0060(17) -0.0051(16) 0.0035(16) C6 0.036(3) 0.036(3) 0.019(3) 0.000(2) 0.007(2) -0.020(2) O7 0.0256(17) 0.0297(18) 0.0261(19) -0.0022(15) -0.0088(15) 0.0040(15) C7 0.039(3) 0.035(3) 0.023(3) 0.006(2) -0.002(2) -0.008(3) C8 0.022(3) 0.022(3) 0.027(3) -0.002(2) 0.002(2) -0.006(2) C9 0.017(2) 0.018(2) 0.027(3) 0.003(2) 0.002(2) -0.007(2) C10 0.020(2) 0.020(2) 0.022(3) -0.001(2) 0.004(2) 0.000(2) C11 0.018(2) 0.023(3) 0.019(3) -0.006(2) 0.001(2) 0.000(2) C12 0.024(3) 0.019(3) 0.023(3) -0.008(2) 0.003(2) -0.001(2) C13 0.026(3) 0.027(3) 0.021(3) -0.009(2) 0.000(2) 0.005(2) C14 0.022(3) 0.039(3) 0.026(3) -0.009(2) -0.003(2) 0.001(2) C15 0.019(3) 0.039(3) 0.024(3) -0.006(2) -0.005(2) 0.006(2) C16 0.014(2) 0.035(3) 0.029(3) -0.003(2) -0.002(2) 0.000(2) C17 0.029(3) 0.031(3) 0.034(3) 0.000(2) -0.005(2) 0.004(2) C18 0.030(3) 0.034(3) 0.030(3) 0.004(2) -0.002(2) 0.004(2) C19 0.034(3) 0.045(3) 0.029(3) 0.006(3) -0.009(2) 0.011(3) C20 0.030(3) 0.033(3) 0.021(3) 0.001(2) -0.007(2) 0.000(2) C21 0.018(2) 0.027(3) 0.018(3) 0.003(2) 0.000(2) 0.000(2) C22 0.018(2) 0.021(3) 0.019(3) 0.003(2) 0.009(2) -0.006(2) C23 0.022(2) 0.029(3) 0.018(3) 0.000(2) -0.006(2) 0.000(2) C24 0.018(2) 0.019(3) 0.024(3) -0.004(2) 0.001(2) 0.007(2) C25 0.023(3) 0.020(3) 0.025(3) 0.000(2) 0.000(2) 0.009(2) C26 0.022(3) 0.019(3) 0.032(3) 0.000(2) 0.002(2) -0.002(2) C27 0.018(2) 0.023(3) 0.026(3) -0.007(2) -0.004(2) 0.001(2) C28 0.063(4) 0.025(3) 0.038(3) -0.002(3) 0.022(3) -0.010(3) C29 0.095(5) 0.024(3) 0.056(4) 0.003(3) 0.042(4) 0.012(3) C30 0.054(4) 0.049(4) 0.051(4) 0.013(3) 0.033(3) 0.029(3) C31 0.024(3) 0.058(4) 0.025(3) 0.005(3) 0.003(2) 0.002(3) C32 0.031(3) 0.032(3) 0.027(3) 0.011(2) -0.002(2) -0.006(2) C33 0.027(3) 0.025(3) 0.041(3) 0.012(3) -0.005(3) 0.008(2) C34 0.027(3) 0.021(3) 0.038(3) 0.004(2) 0.001(2) 0.008(2) C35 0.025(3) 0.026(3) 0.022(3) 0.001(2) 0.000(2) -0.005(2) C36 0.024(3) 0.022(3) 0.030(3) -0.002(2) -0.003(2) 0.003(2) C37 0.031(3) 0.026(3) 0.051(4) -0.004(3) -0.001(3) -0.004(3) C38 0.022(3) 0.036(3) 0.041(3) -0.010(3) 0.001(2) -0.005(2) C39 0.018(2) 0.042(3) 0.034(3) -0.004(3) -0.002(2) 0.002(2) C40 0.016(3) 0.055(4) 0.035(3) -0.005(3) 0.001(2) 0.003(3) C41 0.016(3) 0.051(4) 0.028(3) -0.015(3) -0.007(2) 0.011(3) C42 0.016(2) 0.034(3) 0.036(3) -0.011(2) -0.002(2) 0.004(2) C43 0.028(3) 0.030(3) 0.020(3) -0.006(2) -0.002(2) 0.006(2) C44 0.030(3) 0.025(3) 0.026(3) -0.003(2) 0.005(2) 0.002(2) C45 0.023(2) 0.027(3) 0.022(3) 0.004(2) 0.002(2) 0.002(2) C46 0.022(3) 0.025(3) 0.020(3) 0.004(2) 0.000(2) -0.002(2) O1' 0.0296(17) 0.0320(19) 0.0225(19) 0.0050(15) -0.0015(14) 0.0053(15) C1' 0.031(3) 0.013(2) 0.029(3) -0.002(2) 0.000(2) 0.000(2) O2' 0.0287(17) 0.0184(17) 0.0269(18) 0.0005(14) 0.0107(14) 0.0040(14) C2' 0.028(3) 0.019(3) 0.024(3) 0.002(2) -0.002(2) 0.004(2) O3' 0.0266(17) 0.0284(18) 0.0187(18) 0.0032(15) -0.0012(14) -0.0021(15) C3' 0.022(2) 0.021(3) 0.029(3) 0.003(2) 0.000(2) 0.002(2) O4' 0.0244(17) 0.0249(18) 0.035(2) -0.0089(15) -0.0043(14) 0.0011(14) C4' 0.021(2) 0.027(3) 0.016(3) 0.005(2) -0.002(2) -0.003(2) O5' 0.0299(19) 0.029(2) 0.055(2) -0.0112(17) 0.0073(17) -0.0043(16) C5' 0.020(2) 0.026(3) 0.019(3) 0.007(2) -0.002(2) -0.003(2) O6' 0.046(2) 0.036(2) 0.039(2) 0.0024(18) -0.0164(18) 0.0043(17) C6' 0.022(2) 0.033(3) 0.020(3) 0.002(2) 0.002(2) 0.008(2) O7' 0.041(2) 0.038(2) 0.024(2) 0.0056(16) -0.0056(16) 0.0054(17) C7' 0.036(3) 0.031(3) 0.018(3) -0.001(2) -0.002(2) 0.010(2) C8' 0.017(2) 0.022(3) 0.027(3) 0.000(2) 0.007(2) 0.003(2) C9' 0.012(2) 0.015(2) 0.033(3) 0.002(2) 0.000(2) -0.001(2) C10' 0.021(2) 0.021(2) 0.022(3) 0.003(2) 0.003(2) -0.002(2) C11' 0.016(2) 0.023(3) 0.018(3) 0.002(2) 0.003(2) 0.000(2) C12' 0.019(2) 0.014(2) 0.019(3) 0.000(2) 0.004(2) 0.001(2) C13' 0.021(3) 0.026(3) 0.018(3) 0.005(2) -0.001(2) -0.005(2) C14' 0.023(3) 0.032(3) 0.026(3) -0.002(2) -0.005(2) 0.004(2) C15' 0.017(2) 0.030(3) 0.024(3) -0.002(2) -0.001(2) -0.001(2) C16' 0.018(3) 0.034(3) 0.042(3) -0.001(3) 0.002(2) -0.001(2) C17' 0.040(3) 0.020(3) 0.044(3) -0.005(2) -0.009(3) -0.004(2) C18' 0.049(3) 0.028(3) 0.033(3) -0.003(2) -0.010(3) 0.016(3) C19' 0.063(4) 0.046(3) 0.019(3) -0.006(3) -0.015(3) 0.007(3) C20' 0.058(4) 0.044(3) 0.026(3) 0.003(3) -0.011(3) 0.006(3) C21' 0.035(3) 0.042(3) 0.014(3) -0.002(2) 0.006(2) 0.010(3) C22' 0.043(3) 0.031(3) 0.017(3) -0.003(2) 0.003(2) 0.004(3) C23' 0.052(3) 0.039(3) 0.026(3) 0.003(3) -0.006(3) 0.003(3) C24' 0.052(3) 0.024(3) 0.027(3) 0.000(2) -0.004(3) 0.002(3) C25' 0.112(5) 0.039(3) 0.021(3) -0.004(3) -0.014(3) 0.028(4) C26' 0.094(5) 0.035(3) 0.034(4) -0.010(3) -0.011(3) 0.035(3) C27' 0.052(3) 0.025(3) 0.032(3) 0.000(2) -0.004(3) 0.011(3) C28' 0.040(3) 0.028(3) 0.027(3) 0.004(2) -0.004(2) 0.005(2) C29' 0.039(3) 0.032(3) 0.039(3) 0.009(3) -0.002(3) -0.012(3) C30' 0.031(3) 0.048(4) 0.042(3) 0.019(3) 0.007(3) -0.010(3) C31' 0.027(3) 0.042(3) 0.024(3) 0.010(2) 0.002(2) 0.004(2) C32' 0.027(3) 0.023(3) 0.031(3) -0.005(2) -0.005(2) 0.001(2) C33' 0.024(3) 0.027(3) 0.042(4) -0.003(3) -0.007(2) 0.000(2) C34' 0.023(3) 0.020(3) 0.050(4) 0.009(3) -0.001(2) -0.004(2) C35' 0.021(2) 0.025(3) 0.036(3) 0.002(2) 0.003(2) 0.002(2) C36' 0.020(3) 0.023(3) 0.041(3) -0.007(2) -0.003(2) -0.002(2) C37' 0.034(3) 0.022(3) 0.042(3) -0.008(2) 0.005(2) 0.001(2) C38' 0.027(3) 0.025(3) 0.036(3) 0.006(2) 0.002(2) 0.005(2) C39' 0.020(2) 0.034(3) 0.034(3) 0.006(2) -0.002(2) 0.000(2) C40' 0.018(3) 0.050(4) 0.040(3) 0.003(3) 0.004(2) 0.005(3) C41' 0.018(3) 0.048(4) 0.050(4) 0.012(3) -0.002(2) -0.002(3) C42' 0.019(3) 0.032(3) 0.051(4) 0.009(3) -0.003(3) -0.004(2) C43' 0.044(3) 0.046(3) 0.021(3) 0.006(3) 0.002(2) 0.011(3) C44' 0.050(4) 0.045(3) 0.033(3) 0.006(3) 0.011(3) -0.004(3) C45' 0.041(3) 0.044(3) 0.029(3) -0.006(3) 0.001(3) -0.002(3) C46' 0.041(3) 0.039(3) 0.029(3) -0.004(3) -0.002(3) 0.009(3) C2G 0.040(3) 0.059(4) 0.032(3) -0.001(3) 0.004(3) -0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.381(4) . ? C1 C2 1.388(5) . ? C1 C24 1.398(6) . ? O2 C5 1.380(5) . ? O2 C6 1.443(5) . ? C2 C27 1.389(5) . ? C2 C3 1.515(6) . ? O3 C8 1.372(5) . ? O3 C7 1.429(5) . ? C3 C4 1.500(5) . ? O4 C12 1.382(5) . ? C4 C28 1.379(6) . ? C4 C5 1.386(5) . ? O5 C16 1.386(5) . ? O5 C17 1.441(5) . ? C5 C31 1.387(6) . ? O6 C19 1.419(5) . ? O6 C18 1.428(5) . ? C6 C7 1.498(6) . ? O7 C21 1.376(5) . ? O7 C20 1.428(4) . ? C8 C32 1.389(6) . ? C8 C9 1.405(6) . ? C9 C35 1.383(5) . ? C9 C10 1.505(5) . ? C10 C11 1.523(5) . ? C11 C36 1.382(5) . ? C11 C12 1.391(5) . ? C12 C13 1.392(5) . ? C13 C38 1.395(6) . ? C13 C14 1.519(6) . ? C14 C15 1.517(6) . ? C15 C39 1.384(6) . ? C15 C16 1.399(6) . ? C16 C42 1.385(6) . ? C17 C18 1.502(6) . ? C19 C20 1.502(5) . ? C21 C43 1.386(6) . ? C21 C22 1.398(5) . ? C22 C46 1.381(5) . ? C22 C23 1.514(5) . ? C23 C24 1.504(5) . ? C24 C25 1.397(5) . ? C25 C26 1.384(5) . ? C26 C27 1.386(6) . ? C28 C29 1.373(7) . ? C29 C30 1.367(7) . ? C30 C31 1.381(6) . ? C32 C33 1.379(6) . ? C33 C34 1.374(6) . ? C34 C35 1.379(5) . ? C36 C37 1.400(6) . ? C37 C38 1.374(6) . ? C39 C40 1.380(6) . ? C40 C41 1.375(6) . ? C41 C42 1.392(6) . ? C43 C44 1.392(5) . ? C44 C45 1.376(5) . ? C45 C46 1.394(5) . ? O1' C1' 1.380(5) . ? C1' C2' 1.392(6) . ? C1' C24' 1.393(6) . ? O2' C5' 1.387(5) . ? O2' C6' 1.426(4) . ? C2' C27' 1.381(6) . ? C2' C3' 1.505(6) . ? O3' C8' 1.381(5) . ? O3' C7' 1.429(5) . ? C3' C4' 1.507(5) . ? O4' C12' 1.375(4) . ? C4' C5' 1.392(5) . ? C4' C28' 1.399(5) . ? O5' C16' 1.388(5) . ? O5' C17' 1.447(5) . ? C5' C31' 1.387(6) . ? O6' C19' 1.416(6) . ? O6' C18' 1.417(5) . ? C6' C7' 1.495(5) . ? O7' C21' 1.381(5) . ? O7' C20' 1.421(5) . ? C8' C32' 1.394(6) . ? C8' C9' 1.394(6) . ? C9' C35' 1.382(5) . ? C9' C10' 1.510(5) . ? C10' C11' 1.526(5) . ? C11' C36' 1.389(5) . ? C11' C12' 1.395(5) . ? C12' C13' 1.391(5) . ? C13' C38' 1.394(6) . ? C13' C14' 1.528(5) . ? C14' C15' 1.521(6) . ? C15' C16' 1.384(6) . ? C15' C39' 1.388(6) . ? C16' C42' 1.383(6) . ? C17' C18' 1.488(6) . ? C19' C20' 1.498(6) . ? C21' C43' 1.383(6) . ? C21' C22' 1.394(6) . ? C22' C46' 1.383(6) . ? C22' C23' 1.517(6) . ? C23' C24' 1.510(6) . ? C24' C25' 1.381(6) . ? C25' C26' 1.385(6) . ? C26' C27' 1.372(6) . ? C28' C29' 1.381(6) . ? C29' C30' 1.369(6) . ? C30' C31' 1.385(6) . ? C32' C33' 1.389(6) . ? C33' C34' 1.358(6) . ? C34' C35' 1.399(6) . ? C36' C37' 1.386(5) . ? C37' C38' 1.384(6) . ? C39' C40' 1.397(6) . ? C40' C41' 1.368(6) . ? C41' C42' 1.380(6) . ? C43' C44' 1.379(6) . ? C44' C45' 1.372(6) . ? C45' C46' 1.390(6) . ? Cl2A C1GA 1.792(7) . ? Cl3A C1GA 1.719(7) . ? Cl4A C2G 1.741(6) . ? Cl5A C2G 1.769(5) . ? Cl6A C2G 1.636(5) . ? Cl2C C1GC 1.772(8) . ? Cl3C C1GC 1.746(9) . ? Cl4B C2G 1.732(6) . ? Cl5B C2G 1.751(5) . ? Cl6B C2G 1.865(5) . ? C1GC Cl1C 1.759(8) . ? C1GA Cl1A 1.754(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 O1 C1 C2 122.7(4) . . ? O1 C1 C24 114.7(4) . . ? C2 C1 C24 122.6(4) . . ? C5 O2 C6 118.2(3) . . ? C1 C2 C27 118.0(4) . . ? C1 C2 C3 122.1(4) . . ? C27 C2 C3 119.9(4) . . ? C8 O3 C7 118.0(3) . . ? C4 C3 C2 114.6(3) . . ? C28 C4 C5 117.2(4) . . ? C28 C4 C3 120.3(4) . . ? C5 C4 C3 122.5(4) . . ? C16 O5 C17 119.0(3) . . ? O2 C5 C4 115.5(4) . . ? O2 C5 C31 122.5(4) . . ? C4 C5 C31 121.9(4) . . ? C19 O6 C18 114.8(3) . . ? O2 C6 C7 106.1(3) . . ? C21 O7 C20 118.6(3) . . ? O3 C7 C6 108.4(4) . . ? O3 C8 C32 123.8(4) . . ? O3 C8 C9 116.1(4) . . ? C32 C8 C9 120.1(4) . . ? C35 C9 C8 117.6(4) . . ? C35 C9 C10 120.6(4) . . ? C8 C9 C10 121.7(4) . . ? C9 C10 C11 114.4(3) . . ? C36 C11 C12 118.1(4) . . ? C36 C11 C10 123.0(4) . . ? C12 C11 C10 118.9(4) . . ? O4 C12 C11 115.7(4) . . ? O4 C12 C13 121.9(4) . . ? C11 C12 C13 122.3(4) . . ? C12 C13 C38 117.4(4) . . ? C12 C13 C14 122.9(4) . . ? C38 C13 C14 119.7(4) . . ? C15 C14 C13 114.4(4) . . ? C39 C15 C16 117.4(4) . . ? C39 C15 C14 120.9(4) . . ? C16 C15 C14 121.7(4) . . ? C42 C16 O5 123.3(4) . . ? C42 C16 C15 121.8(4) . . ? O5 C16 C15 114.9(4) . . ? O5 C17 C18 107.3(4) . . ? O6 C18 C17 108.9(4) . . ? O6 C19 C20 114.3(4) . . ? O7 C20 C19 107.3(3) . . ? O7 C21 C43 124.3(4) . . ? O7 C21 C22 114.7(4) . . ? C43 C21 C22 121.0(4) . . ? C46 C22 C21 118.5(4) . . ? C46 C22 C23 123.9(4) . . ? C21 C22 C23 117.6(4) . . ? C24 C23 C22 116.7(3) . . ? C1 C24 C25 117.1(4) . . ? C1 C24 C23 122.2(4) . . ? C25 C24 C23 120.7(4) . . ? C26 C25 C24 121.7(4) . . ? C25 C26 C27 119.1(4) . . ? C26 C27 C2 121.4(4) . . ? C29 C28 C4 121.8(5) . . ? C30 C29 C28 120.0(5) . . ? C29 C30 C31 120.4(5) . . ? C30 C31 C5 118.7(5) . . ? C33 C32 C8 120.5(4) . . ? C34 C33 C32 120.0(4) . . ? C33 C34 C35 119.6(4) . . ? C34 C35 C9 122.2(4) . . ? C11 C36 C37 121.3(4) . . ? C38 C37 C36 118.7(4) . . ? C37 C38 C13 122.1(4) . . ? C40 C39 C15 122.2(4) . . ? C41 C40 C39 119.0(5) . . ? C40 C41 C42 121.1(4) . . ? C16 C42 C41 118.5(4) . . ? C21 C43 C44 119.1(4) . . ? C45 C44 C43 120.9(4) . . ? C44 C45 C46 119.2(4) . . ? C22 C46 C45 121.3(4) . . ? O1' C1' C2' 123.4(4) . . ? O1' C1' C24' 115.2(4) . . ? C2' C1' C24' 121.4(4) . . ? C5' O2' C6' 118.1(3) . . ? C27' C2' C1' 118.2(4) . . ? C27' C2' C3' 120.8(4) . . ? C1' C2' C3' 121.0(4) . . ? C8' O3' C7' 117.5(3) . . ? C2' C3' C4' 114.0(3) . . ? C5' C4' C28' 116.3(4) . . ? C5' C4' C3' 122.5(4) . . ? C28' C4' C3' 121.2(4) . . ? C16' O5' C17' 119.3(3) . . ? C31' C5' O2' 122.4(4) . . ? C31' C5' C4' 122.8(4) . . ? O2' C5' C4' 114.7(4) . . ? C19' O6' C18' 114.9(4) . . ? O2' C6' C7' 106.4(3) . . ? C21' O7' C20' 118.9(4) . . ? O3' C7' C6' 108.6(3) . . ? O3' C8' C32' 122.7(4) . . ? O3' C8' C9' 116.2(4) . . ? C32' C8' C9' 121.1(4) . . ? C35' C9' C8' 117.9(4) . . ? C35' C9' C10' 119.3(4) . . ? C8' C9' C10' 122.7(4) . . ? C9' C10' C11' 113.5(3) . . ? C36' C11' C12' 118.0(4) . . ? C36' C11' C10' 122.5(4) . . ? C12' C11' C10' 119.5(4) . . ? O4' C12' C13' 122.1(4) . . ? O4' C12' C11' 115.5(3) . . ? C13' C12' C11' 122.4(4) . . ? C12' C13' C38' 117.5(4) . . ? C12' C13' C14' 123.6(4) . . ? C38' C13' C14' 119.0(4) . . ? C15' C14' C13' 113.3(4) . . ? C16' C15' C39' 118.2(4) . . ? C16' C15' C14' 121.7(4) . . ? C39' C15' C14' 120.1(4) . . ? C15' C16' C42' 121.5(4) . . ? C15' C16' O5' 114.4(4) . . ? C42' C16' O5' 124.1(4) . . ? O5' C17' C18' 106.6(4) . . ? O6' C18' C17' 108.4(4) . . ? O6' C19' C20' 114.5(4) . . ? O7' C20' C19' 107.7(4) . . ? O7' C21' C43' 124.5(4) . . ? O7' C21' C22' 114.3(4) . . ? C43' C21' C22' 121.2(5) . . ? C46' C22' C21' 117.8(4) . . ? C46' C22' C23' 124.0(4) . . ? C21' C22' C23' 118.1(4) . . ? C24' C23' C22' 116.4(4) . . ? C25' C24' C1' 118.4(4) . . ? C25' C24' C23' 120.5(4) . . ? C1' C24' C23' 121.1(4) . . ? C24' C25' C26' 121.0(5) . . ? C27' C26' C25' 119.5(5) . . ? C26' C27' C2' 121.5(5) . . ? C29' C28' C4' 122.2(4) . . ? C30' C29' C28' 119.2(4) . . ? C29' C30' C31' 121.4(4) . . ? C30' C31' C5' 118.1(4) . . ? C33' C32' C8' 119.1(4) . . ? C34' C33' C32' 121.0(4) . . ? C33' C34' C35' 119.3(4) . . ? C9' C35' C34' 121.6(4) . . ? C37' C36' C11' 121.1(4) . . ? C38' C37' C36' 119.3(4) . . ? C37' C38' C13' 121.6(4) . . ? C15' C39' C40' 120.8(4) . . ? C41' C40' C39' 119.3(4) . . ? C40' C41' C42' 121.0(5) . . ? C41' C42' C16' 119.1(4) . . ? C44' C43' C21' 119.5(5) . . ? C45' C44' C43' 120.6(5) . . ? C44' C45' C46' 119.4(5) . . ? C22' C46' C45' 121.4(5) . . ? Cl3C C1GC Cl1C 105.8(5) . . ? Cl3C C1GC Cl2C 112.5(6) . . ? Cl1C C1GC Cl2C 112.4(6) . . ? Cl3A C1GA Cl1A 112.4(4) . . ? Cl3A C1GA Cl2A 113.8(4) . . ? Cl1A C1GA Cl2A 106.6(5) . . ? Cl6A C2G Cl4B 130.9(3) . . ? Cl6A C2G Cl4A 115.7(3) . . ? Cl4B C2G Cl4A 16.07(19) . . ? Cl6A C2G Cl5B 94.3(3) . . ? Cl4B C2G Cl5B 113.1(3) . . ? Cl4A C2G Cl5B 124.6(3) . . ? Cl6A C2G Cl5A 116.8(3) . . ? Cl4B C2G Cl5A 95.6(3) . . ? Cl4A C2G Cl5A 109.8(3) . . ? Cl5B C2G Cl5A 22.50(13) . . ? Cl6A C2G Cl6B 24.10(16) . . ? Cl4B C2G Cl6B 107.5(3) . . ? Cl4A C2G Cl6B 93.0(3) . . ? Cl5B C2G Cl6B 102.2(3) . . ? Cl5A C2G Cl6B 122.6(3) . . ? 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 O1 C1 C2 C27 178.2(3) . . . . ? C24 C1 C2 C27 -0.3(6) . . . . ? O1 C1 C2 C3 -2.0(6) . . . . ? C24 C1 C2 C3 179.4(4) . . . . ? C1 C2 C3 C4 -76.9(5) . . . . ? C27 C2 C3 C4 102.8(4) . . . . ? C2 C3 C4 C28 -79.4(5) . . . . ? C2 C3 C4 C5 102.4(5) . . . . ? C6 O2 C5 C4 144.5(4) . . . . ? C6 O2 C5 C31 -38.4(6) . . . . ? C28 C4 C5 O2 179.6(4) . . . . ? C3 C4 C5 O2 -2.2(6) . . . . ? C28 C4 C5 C31 2.5(6) . . . . ? C3 C4 C5 C31 -179.3(4) . . . . ? C5 O2 C6 C7 -153.0(4) . . . . ? C8 O3 C7 C6 164.6(3) . . . . ? O2 C6 C7 O3 -62.8(4) . . . . ? C7 O3 C8 C32 7.5(6) . . . . ? C7 O3 C8 C9 -171.8(3) . . . . ? O3 C8 C9 C35 178.7(3) . . . . ? C32 C8 C9 C35 -0.7(6) . . . . ? O3 C8 C9 C10 -2.5(6) . . . . ? C32 C8 C9 C10 178.2(4) . . . . ? C35 C9 C10 C11 93.1(4) . . . . ? C8 C9 C10 C11 -85.7(5) . . . . ? C9 C10 C11 C36 0.2(6) . . . . ? C9 C10 C11 C12 -179.2(4) . . . . ? C36 C11 C12 O4 -178.1(4) . . . . ? C10 C11 C12 O4 1.3(5) . . . . ? C36 C11 C12 C13 0.5(6) . . . . ? C10 C11 C12 C13 179.9(4) . . . . ? O4 C12 C13 C38 178.7(4) . . . . ? C11 C12 C13 C38 0.2(6) . . . . ? O4 C12 C13 C14 -2.2(6) . . . . ? C11 C12 C13 C14 179.3(4) . . . . ? C12 C13 C14 C15 -86.5(5) . . . . ? C38 C13 C14 C15 92.5(5) . . . . ? C13 C14 C15 C39 -81.9(5) . . . . ? C13 C14 C15 C16 99.2(5) . . . . ? C17 O5 C16 C42 -11.1(6) . . . . ? C17 O5 C16 C15 171.1(4) . . . . ? C39 C15 C16 C42 -1.1(6) . . . . ? C14 C15 C16 C42 177.8(4) . . . . ? C39 C15 C16 O5 176.7(4) . . . . ? C14 C15 C16 O5 -4.4(6) . . . . ? C16 O5 C17 C18 -178.5(4) . . . . ? C19 O6 C18 C17 -178.8(3) . . . . ? O5 C17 C18 O6 62.9(4) . . . . ? C18 O6 C19 C20 82.4(5) . . . . ? C21 O7 C20 C19 -178.7(3) . . . . ? O6 C19 C20 O7 -75.1(5) . . . . ? C20 O7 C21 C43 -0.3(6) . . . . ? C20 O7 C21 C22 179.3(3) . . . . ? O7 C21 C22 C46 179.7(3) . . . . ? C43 C21 C22 C46 -0.6(6) . . . . ? O7 C21 C22 C23 1.2(5) . . . . ? C43 C21 C22 C23 -179.1(4) . . . . ? C46 C22 C23 C24 9.4(6) . . . . ? C21 C22 C23 C24 -172.2(4) . . . . ? O1 C1 C24 C25 -176.3(3) . . . . ? C2 C1 C24 C25 2.4(6) . . . . ? O1 C1 C24 C23 6.1(5) . . . . ? C2 C1 C24 C23 -175.2(4) . . . . ? C22 C23 C24 C1 -84.7(5) . . . . ? C22 C23 C24 C25 97.8(4) . . . . ? C1 C24 C25 C26 -2.5(6) . . . . ? C23 C24 C25 C26 175.1(4) . . . . ? C24 C25 C26 C27 0.5(6) . . . . ? C25 C26 C27 C2 1.7(6) . . . . ? C1 C2 C27 C26 -1.8(6) . . . . ? C3 C2 C27 C26 178.5(4) . . . . ? C5 C4 C28 C29 -1.8(7) . . . . ? C3 C4 C28 C29 179.8(5) . . . . ? C4 C28 C29 C30 0.5(8) . . . . ? C28 C29 C30 C31 0.3(8) . . . . ? C29 C30 C31 C5 0.3(7) . . . . ? O2 C5 C31 C30 -178.6(4) . . . . ? C4 C5 C31 C30 -1.7(7) . . . . ? O3 C8 C32 C33 -178.9(4) . . . . ? C9 C8 C32 C33 0.4(6) . . . . ? C8 C32 C33 C34 -0.3(6) . . . . ? C32 C33 C34 C35 0.4(6) . . . . ? C33 C34 C35 C9 -0.7(6) . . . . ? C8 C9 C35 C34 0.8(6) . . . . ? C10 C9 C35 C34 -178.0(4) . . . . ? C12 C11 C36 C37 -0.5(6) . . . . ? C10 C11 C36 C37 -179.9(4) . . . . ? C11 C36 C37 C38 -0.2(7) . . . . ? C36 C37 C38 C13 1.0(7) . . . . ? C12 C13 C38 C37 -1.0(7) . . . . ? C14 C13 C38 C37 180.0(4) . . . . ? C16 C15 C39 C40 0.9(7) . . . . ? C14 C15 C39 C40 -178.1(4) . . . . ? C15 C39 C40 C41 -0.1(7) . . . . ? C39 C40 C41 C42 -0.4(7) . . . . ? O5 C16 C42 C41 -177.0(4) . . . . ? C15 C16 C42 C41 0.7(7) . . . . ? C40 C41 C42 C16 0.1(6) . . . . ? O7 C21 C43 C44 -179.4(4) . . . . ? C22 C21 C43 C44 1.0(6) . . . . ? C21 C43 C44 C45 -1.5(6) . . . . ? C43 C44 C45 C46 1.6(6) . . . . ? C21 C22 C46 C45 0.7(6) . . . . ? C23 C22 C46 C45 179.1(4) . . . . ? C44 C45 C46 C22 -1.2(6) . . . . ? O1' C1' C2' C27' 177.3(4) . . . . ? C24' C1' C2' C27' -2.9(6) . . . . ? O1' C1' C2' C3' -5.9(6) . . . . ? C24' C1' C2' C3' 173.9(4) . . . . ? C27' C2' C3' C4' 105.6(5) . . . . ? C1' C2' C3' C4' -71.2(5) . . . . ? C2' C3' C4' C5' 105.3(5) . . . . ? C2' C3' C4' C28' -73.6(5) . . . . ? C6' O2' C5' C31' -20.3(6) . . . . ? C6' O2' C5' C4' 162.3(4) . . . . ? C28' C4' C5' C31' -1.0(6) . . . . ? C3' C4' C5' C31' -180.0(4) . . . . ? C28' C4' C5' O2' 176.4(4) . . . . ? C3' C4' C5' O2' -2.6(6) . . . . ? C5' O2' C6' C7' -167.6(3) . . . . ? C8' O3' C7' C6' 167.8(3) . . . . ? O2' C6' C7' O3' -68.2(4) . . . . ? C7' O3' C8' C32' 2.6(5) . . . . ? C7' O3' C8' C9' -177.9(3) . . . . ? O3' C8' C9' C35' 179.2(3) . . . . ? C32' C8' C9' C35' -1.3(6) . . . . ? O3' C8' C9' C10' -5.3(6) . . . . ? C32' C8' C9' C10' 174.2(4) . . . . ? C35' C9' C10' C11' 83.4(5) . . . . ? C8' C9' C10' C11' -92.1(5) . . . . ? C9' C10' C11' C36' -0.9(6) . . . . ? C9' C10' C11' C12' 178.9(4) . . . . ? C36' C11' C12' O4' -178.6(4) . . . . ? C10' C11' C12' O4' 1.5(5) . . . . ? C36' C11' C12' C13' 1.0(6) . . . . ? C10' C11' C12' C13' -178.9(4) . . . . ? O4' C12' C13' C38' 178.2(4) . . . . ? C11' C12' C13' C38' -1.4(6) . . . . ? O4' C12' C13' C14' -3.4(6) . . . . ? C11' C12' C13' C14' 177.0(4) . . . . ? C12' C13' C14' C15' -85.3(5) . . . . ? C38' C13' C14' C15' 93.1(5) . . . . ? C13' C14' C15' C16' 97.0(5) . . . . ? C13' C14' C15' C39' -84.6(5) . . . . ? C39' C15' C16' C42' -1.9(7) . . . . ? C14' C15' C16' C42' 176.5(4) . . . . ? C39' C15' C16' O5' 177.5(4) . . . . ? C14' C15' C16' O5' -4.1(6) . . . . ? C17' O5' C16' C15' 170.1(4) . . . . ? C17' O5' C16' C42' -10.6(6) . . . . ? C16' O5' C17' C18' 178.5(4) . . . . ? C19' O6' C18' C17' 172.1(4) . . . . ? O5' C17' C18' O6' 63.4(5) . . . . ? C18' O6' C19' C20' 83.8(5) . . . . ? C21' O7' C20' C19' 173.4(4) . . . . ? O6' C19' C20' O7' -72.9(5) . . . . ? C20' O7' C21' C43' -0.2(6) . . . . ? C20' O7' C21' C22' 179.4(4) . . . . ? O7' C21' C22' C46' -179.9(4) . . . . ? C43' C21' C22' C46' -0.4(6) . . . . ? O7' C21' C22' C23' 1.5(6) . . . . ? C43' C21' C22' C23' -178.9(4) . . . . ? C46' C22' C23' C24' 15.3(7) . . . . ? C21' C22' C23' C24' -166.2(4) . . . . ? O1' C1' C24' C25' -177.5(4) . . . . ? C2' C1' C24' C25' 2.7(7) . . . . ? O1' C1' C24' C23' 5.5(6) . . . . ? C2' C1' C24' C23' -174.3(4) . . . . ? C22' C23' C24' C25' 97.6(6) . . . . ? C22' C23' C24' C1' -85.4(6) . . . . ? C1' C24' C25' C26' -0.3(8) . . . . ? C23' C24' C25' C26' 176.8(5) . . . . ? C24' C25' C26' C27' -1.8(9) . . . . ? C25' C26' C27' C2' 1.6(8) . . . . ? C1' C2' C27' C26' 0.7(7) . . . . ? C3' C2' C27' C26' -176.1(5) . . . . ? C5' C4' C28' C29' -0.7(6) . . . . ? C3' C4' C28' C29' 178.3(4) . . . . ? C4' C28' C29' C30' 2.0(7) . . . . ? C28' C29' C30' C31' -1.7(7) . . . . ? C29' C30' C31' C5' 0.1(7) . . . . ? O2' C5' C31' C30' -175.9(4) . . . . ? C4' C5' C31' C30' 1.3(7) . . . . ? O3' C8' C32' C33' -179.6(3) . . . . ? C9' C8' C32' C33' 1.0(6) . . . . ? C8' C32' C33' C34' -0.3(6) . . . . ? C32' C33' C34' C35' -0.1(6) . . . . ? C8' C9' C35' C34' 0.9(6) . . . . ? C10' C9' C35' C34' -174.7(4) . . . . ? C33' C34' C35' C9' -0.2(6) . . . . ? C12' C11' C36' C37' -0.3(6) . . . . ? C10' C11' C36' C37' 179.5(4) . . . . ? C11' C36' C37' C38' 0.2(7) . . . . ? C36' C37' C38' C13' -0.6(7) . . . . ? C12' C13' C38' C37' 1.2(6) . . . . ? C14' C13' C38' C37' -177.3(4) . . . . ? C16' C15' C39' C40' 0.8(6) . . . . ? C14' C15' C39' C40' -177.7(4) . . . . ? C15' C39' C40' C41' 0.0(7) . . . . ? C39' C40' C41' C42' 0.4(7) . . . . ? C40' C41' C42' C16' -1.5(7) . . . . ? C15' C16' C42' C41' 2.3(7) . . . . ? O5' C16' C42' C41' -177.0(4) . . . . ? O7' C21' C43' C44' -179.6(4) . . . . ? C22' C21' C43' C44' 0.9(7) . . . . ? C21' C43' C44' C45' -0.9(7) . . . . ? C43' C44' C45' C46' 0.4(7) . . . . ? C21' C22' C46' C45' -0.1(7) . . . . ? C23' C22' C46' C45' 178.4(4) . . . . ? C44' C45' C46' C22' 0.0(7) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.96 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.761 _refine_diff_density_min -0.850 _refine_diff_density_rms 0.074 _exptl_crystal_recrystallization_method 'slow evaporation from CHCl3 solution'