# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Philip Chan' _publ_contact_author_email WAIHONG@NTU.EDU.SG _publ_section_title ; Unexpected Iron(III) Chloride-Catalysed Dimerisation of 1,1,3-Trisubstituted-prop-2-yn-1-ols as an Expedient Route to Highly Conjugated Indenes ; loop_ _publ_author_name 'Philip Chan' 'Weidong Rao.' # Attachment 'chan22m.cif' data_chan22m _database_code_depnum_ccdc_archive 'CCDC 726882' #TrackingRef 'chan22m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H32' _chemical_formula_sum 'C38 H32' _chemical_formula_weight 488.64 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 12.3141(3) _cell_length_b 20.8168(6) _cell_length_c 11.1136(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.158(2) _cell_angle_gamma 90.00 _cell_volume 2691.08(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6111 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 29.27 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9826 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _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 29583 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 28.00 _reflns_number_total 6429 _reflns_number_gt 4766 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.7883P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6429 _refine_ls_number_parameters 353 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1236 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.032 _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 C1 C 0.32610(13) 0.31785(7) 0.49602(15) 0.0326(3) Uani 1 1 d . . . H1 H 0.3525 0.3499 0.4513 0.039 Uiso 1 1 calc R . . C2 C 0.34159(15) 0.25358(8) 0.47437(16) 0.0420(4) Uani 1 1 d . . . H2 H 0.3795 0.2416 0.4158 0.050 Uiso 1 1 calc R . . C3 C 0.30215(16) 0.20694(8) 0.53771(18) 0.0484(5) Uani 1 1 d . . . H3 H 0.3129 0.1628 0.5229 0.058 Uiso 1 1 calc R . . C4 C 0.24725(17) 0.22424(8) 0.62220(19) 0.0505(5) Uani 1 1 d . . . H4 H 0.2195 0.1919 0.6650 0.061 Uiso 1 1 calc R . . C5 C 0.23203(14) 0.28838(8) 0.64565(16) 0.0384(4) Uani 1 1 d . . . H5 H 0.1943 0.2999 0.7046 0.046 Uiso 1 1 calc R . . C6 C 0.27206(12) 0.33592(6) 0.58280(13) 0.0268(3) Uani 1 1 d . . . C7 C 0.26167(12) 0.40240(7) 0.61230(13) 0.0274(3) Uani 1 1 d . . . C8 C 0.25547(11) 0.45642(6) 0.64644(13) 0.0254(3) Uani 1 1 d . . . C9 C 0.24935(11) 0.51968(6) 0.69294(12) 0.0222(3) Uani 1 1 d . . . C10 C 0.29108(11) 0.57755(6) 0.64600(12) 0.0231(3) Uani 1 1 d . . . C11 C 0.34108(12) 0.58461(7) 0.55194(13) 0.0298(3) Uani 1 1 d . . . H11 H 0.3507 0.5487 0.5035 0.036 Uiso 1 1 calc R . . C12 C 0.37687(13) 0.64561(8) 0.53016(14) 0.0356(4) Uani 1 1 d . . . H12 H 0.4109 0.6516 0.4657 0.043 Uiso 1 1 calc R . . C13 C 0.36342(14) 0.69773(8) 0.60147(15) 0.0381(4) Uani 1 1 d . . . H13 H 0.3883 0.7391 0.5853 0.046 Uiso 1 1 calc R . . C14 C 0.31392(13) 0.69026(7) 0.69646(14) 0.0327(3) Uani 1 1 d . . . H14 H 0.3061 0.7260 0.7460 0.039 Uiso 1 1 calc R . . C15 C 0.27613(11) 0.62993(6) 0.71798(12) 0.0237(3) Uani 1 1 d . . . C16 C 0.22012(11) 0.60835(6) 0.81418(12) 0.0209(3) Uani 1 1 d . . . C17 C 0.09710(11) 0.63565(6) 0.78587(13) 0.0256(3) Uani 1 1 d . A . H17 H 0.0561 0.6111 0.8353 0.031 Uiso 1 1 calc R . . C18 C 0.08192(14) 0.70872(7) 0.80179(15) 0.0355(4) Uani 1 1 d D . . H18C H 0.0330 0.7192 0.8542 0.043 Uiso 0.414(18) 1 calc PR A 2 H18D H 0.1553 0.7328 0.8312 0.043 Uiso 0.414(18) 1 calc PR A 2 H18A H 0.0497 0.7194 0.8701 0.043 Uiso 0.586(18) 1 d PR A 1 H18B H 0.1519 0.7343 0.8105 0.043 Uiso 0.586(18) 1 d PR A 1 C19 C -0.0197(8) 0.7077(4) 0.6777(8) 0.058(2) Uani 0.586(18) 1 d PDU A 1 H19A H -0.0165 0.7420 0.6171 0.070 Uiso 0.586(18) 1 calc PR A 1 H19B H -0.0955 0.7071 0.6906 0.070 Uiso 0.586(18) 1 calc PR A 1 C19A C 0.0190(10) 0.7137(4) 0.6573(8) 0.045(2) Uani 0.414(18) 1 d PDU A 2 H19C H -0.0591 0.7323 0.6354 0.054 Uiso 0.414(18) 1 calc PR A 2 H19D H 0.0642 0.7359 0.6108 0.054 Uiso 0.414(18) 1 calc PR A 2 C20 C 0.01912(13) 0.64119(8) 0.64478(14) 0.0352(4) Uani 1 1 d D . . H20C H 0.0561 0.6258 0.5833 0.042 Uiso 0.414(18) 1 calc PR A 2 H20D H -0.0577 0.6215 0.6274 0.042 Uiso 0.414(18) 1 calc PR A 2 H20A H 0.0608 0.6364 0.5828 0.042 Uiso 0.586(18) 1 d PR A 1 H20B H -0.0494 0.6130 0.6225 0.042 Uiso 0.586(18) 1 d PR A 1 C21 C 0.29559(11) 0.62264(6) 0.95174(12) 0.0213(3) Uani 1 1 d . . . C22 C 0.24796(12) 0.63011(6) 1.04834(13) 0.0258(3) Uani 1 1 d . . . H22 H 0.1667 0.6312 1.0276 0.031 Uiso 1 1 calc R . . C23 C 0.31724(13) 0.63597(7) 1.17458(14) 0.0317(3) Uani 1 1 d . . . H23 H 0.2834 0.6407 1.2395 0.038 Uiso 1 1 calc R . . C24 C 0.43554(13) 0.63484(7) 1.20585(14) 0.0326(3) Uani 1 1 d . . . H24 H 0.4831 0.6381 1.2924 0.039 Uiso 1 1 calc R . . C25 C 0.48420(12) 0.62895(7) 1.11103(14) 0.0291(3) Uani 1 1 d . . . H25 H 0.5655 0.6288 1.1322 0.035 Uiso 1 1 calc R . . C26 C 0.41501(11) 0.62329(6) 0.98494(13) 0.0249(3) Uani 1 1 d . . . H26 H 0.4494 0.6198 0.9202 0.030 Uiso 1 1 calc R . . C27 C 0.20978(11) 0.53510(6) 0.78952(12) 0.0210(3) Uani 1 1 d . . . C28 C 0.15874(11) 0.48905(6) 0.85774(13) 0.0226(3) Uani 1 1 d . . . C29 C 0.06288(12) 0.45692(6) 0.79348(14) 0.0264(3) Uani 1 1 d . . . C30 C -0.01150(12) 0.45360(7) 0.65452(14) 0.0308(3) Uani 1 1 d . . . H30A H 0.0323 0.4550 0.5941 0.037 Uiso 1 1 calc R . . H30B H -0.0757 0.4848 0.6304 0.037 Uiso 1 1 calc R . . C31 C -0.04659(15) 0.38516(8) 0.68160(16) 0.0415(4) Uani 1 1 d . . . H31A H -0.0047 0.3506 0.6542 0.050 Uiso 1 1 calc R . . H31B H -0.1306 0.3775 0.6494 0.050 Uiso 1 1 calc R . . C32 C 0.00121(13) 0.39980(7) 0.82618(15) 0.0350(4) Uani 1 1 d . . . H32A H -0.0584 0.4115 0.8641 0.042 Uiso 1 1 calc R . . H32B H 0.0533 0.3663 0.8771 0.042 Uiso 1 1 calc R . . C33 C 0.22118(11) 0.47619(6) 0.99508(13) 0.0236(3) Uani 1 1 d . . . C34 C 0.16288(13) 0.46299(7) 1.08084(14) 0.0301(3) Uani 1 1 d . . . H34 H 0.0812 0.4617 1.0516 0.036 Uiso 1 1 calc R . . C35 C 0.22322(15) 0.45174(7) 1.20837(15) 0.0380(4) Uani 1 1 d . . . H35 H 0.1827 0.4426 1.2658 0.046 Uiso 1 1 calc R . . C36 C 0.34190(15) 0.45376(7) 1.25231(15) 0.0385(4) Uani 1 1 d . . . H36 H 0.3828 0.4467 1.3400 0.046 Uiso 1 1 calc R . . C37 C 0.40091(13) 0.46607(7) 1.16849(15) 0.0339(3) Uani 1 1 d . . . H37 H 0.4826 0.4672 1.1984 0.041 Uiso 1 1 calc R . . C38 C 0.34113(12) 0.47677(6) 1.04090(14) 0.0265(3) Uani 1 1 d . . . H38 H 0.3824 0.4846 0.9836 0.032 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 C1 0.0373(8) 0.0256(7) 0.0341(8) -0.0040(6) 0.0108(6) 0.0031(6) C2 0.0485(9) 0.0334(9) 0.0426(9) -0.0110(7) 0.0129(8) 0.0091(7) C3 0.0613(11) 0.0230(8) 0.0540(11) -0.0059(7) 0.0095(9) 0.0097(7) C4 0.0692(12) 0.0273(8) 0.0552(12) 0.0088(8) 0.0209(10) 0.0008(8) C5 0.0489(9) 0.0315(8) 0.0362(9) 0.0021(6) 0.0161(7) 0.0045(7) C6 0.0286(7) 0.0221(7) 0.0249(7) -0.0034(5) 0.0025(5) 0.0038(5) C7 0.0288(7) 0.0262(7) 0.0255(7) -0.0032(5) 0.0063(6) 0.0022(5) C8 0.0258(6) 0.0263(7) 0.0242(7) -0.0023(5) 0.0083(5) 0.0008(5) C9 0.0234(6) 0.0212(6) 0.0212(6) -0.0034(5) 0.0065(5) -0.0003(5) C10 0.0233(6) 0.0252(7) 0.0196(6) -0.0015(5) 0.0055(5) -0.0020(5) C11 0.0298(7) 0.0391(8) 0.0215(7) -0.0053(6) 0.0098(6) -0.0031(6) C12 0.0356(8) 0.0510(10) 0.0235(7) 0.0025(7) 0.0141(6) -0.0084(7) C13 0.0493(9) 0.0352(8) 0.0319(8) 0.0035(6) 0.0162(7) -0.0138(7) C14 0.0458(8) 0.0256(7) 0.0289(8) -0.0007(6) 0.0149(7) -0.0074(6) C15 0.0293(7) 0.0226(6) 0.0187(6) 0.0007(5) 0.0073(5) -0.0027(5) C16 0.0266(6) 0.0176(6) 0.0196(6) -0.0009(5) 0.0091(5) -0.0008(5) C17 0.0279(7) 0.0226(7) 0.0246(7) -0.0024(5) 0.0065(5) 0.0023(5) C18 0.0380(8) 0.0261(7) 0.0397(9) -0.0037(6) 0.0089(7) 0.0086(6) C19 0.058(4) 0.045(3) 0.053(3) -0.008(2) -0.009(3) 0.022(2) C19A 0.048(4) 0.035(3) 0.042(3) 0.014(2) 0.001(3) 0.009(3) C20 0.0327(7) 0.0390(9) 0.0284(8) -0.0024(6) 0.0025(6) 0.0057(6) C21 0.0272(6) 0.0167(6) 0.0203(6) -0.0001(5) 0.0084(5) -0.0008(5) C22 0.0272(7) 0.0270(7) 0.0253(7) -0.0012(5) 0.0114(5) -0.0022(5) C23 0.0371(8) 0.0372(8) 0.0238(7) -0.0033(6) 0.0143(6) -0.0028(6) C24 0.0352(8) 0.0385(8) 0.0216(7) -0.0016(6) 0.0058(6) -0.0049(6) C25 0.0269(7) 0.0289(7) 0.0289(7) 0.0006(6) 0.0059(6) -0.0033(5) C26 0.0291(7) 0.0231(7) 0.0255(7) -0.0011(5) 0.0129(6) -0.0017(5) C27 0.0228(6) 0.0187(6) 0.0206(6) -0.0003(5) 0.0060(5) -0.0009(5) C28 0.0275(6) 0.0178(6) 0.0252(7) 0.0007(5) 0.0122(5) 0.0014(5) C29 0.0297(7) 0.0223(7) 0.0298(7) -0.0001(5) 0.0134(6) -0.0020(5) C30 0.0285(7) 0.0313(8) 0.0311(8) -0.0008(6) 0.0075(6) -0.0036(6) C31 0.0386(8) 0.0381(9) 0.0431(10) -0.0028(7) 0.0069(7) -0.0141(7) C32 0.0373(8) 0.0303(8) 0.0400(9) 0.0007(6) 0.0161(7) -0.0099(6) C33 0.0318(7) 0.0149(6) 0.0256(7) 0.0007(5) 0.0115(6) 0.0019(5) C34 0.0371(8) 0.0255(7) 0.0322(8) 0.0033(6) 0.0174(6) 0.0025(6) C35 0.0556(10) 0.0322(8) 0.0325(8) 0.0062(6) 0.0230(7) 0.0038(7) C36 0.0550(10) 0.0308(8) 0.0265(8) 0.0052(6) 0.0089(7) 0.0055(7) C37 0.0372(8) 0.0270(7) 0.0327(8) 0.0015(6) 0.0051(6) 0.0047(6) C38 0.0321(7) 0.0204(6) 0.0280(7) 0.0006(5) 0.0113(6) 0.0025(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.384(2) . ? C1 C6 1.391(2) . ? C2 C3 1.378(3) . ? C3 C4 1.373(3) . ? C4 C5 1.385(2) . ? C5 C6 1.391(2) . ? C6 C7 1.4375(19) . ? C7 C8 1.1972(19) . ? C8 C9 1.4257(18) . ? C9 C27 1.3549(19) . ? C9 C10 1.4709(19) . ? C10 C11 1.384(2) . ? C10 C15 1.3998(19) . ? C11 C12 1.391(2) . ? C12 C13 1.385(2) . ? C13 C14 1.390(2) . ? C14 C15 1.3872(19) . ? C15 C16 1.5181(19) . ? C16 C21 1.5352(17) . ? C16 C27 1.5471(17) . ? C16 C17 1.5504(18) . ? C17 C18 1.5498(19) . ? C17 C20 1.5511(19) . ? C18 C19 1.528(6) . ? C18 C19A 1.540(8) . ? C19 C20 1.548(6) . ? C19A C20 1.515(8) . ? C21 C22 1.3907(19) . ? C21 C26 1.3938(18) . ? C22 C23 1.3875(19) . ? C23 C24 1.383(2) . ? C24 C25 1.378(2) . ? C25 C26 1.3856(19) . ? C27 C28 1.4838(18) . ? C28 C29 1.3408(18) . ? C28 C33 1.4907(18) . ? C29 C30 1.5167(19) . ? C29 C32 1.5178(19) . ? C30 C31 1.547(2) . ? C31 C32 1.549(2) . ? C33 C38 1.3955(19) . ? C33 C34 1.396(2) . ? C34 C35 1.387(2) . ? C35 C36 1.381(2) . ? C36 C37 1.380(2) . ? C37 C38 1.385(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 C2 C1 C6 120.43(15) . . ? C3 C2 C1 120.05(16) . . ? C4 C3 C2 119.99(15) . . ? C3 C4 C5 120.60(17) . . ? C4 C5 C6 119.94(16) . . ? C1 C6 C5 118.99(13) . . ? C1 C6 C7 121.12(14) . . ? C5 C6 C7 119.83(14) . . ? C8 C7 C6 175.00(15) . . ? C7 C8 C9 177.37(15) . . ? C27 C9 C8 125.56(13) . . ? C27 C9 C10 110.20(11) . . ? C8 C9 C10 124.18(12) . . ? C11 C10 C15 121.57(13) . . ? C11 C10 C9 130.43(13) . . ? C15 C10 C9 107.97(12) . . ? C10 C11 C12 118.23(14) . . ? C13 C12 C11 120.75(14) . . ? C12 C13 C14 120.76(14) . . ? C15 C14 C13 119.19(14) . . ? C14 C15 C10 119.49(13) . . ? C14 C15 C16 130.16(13) . . ? C10 C15 C16 110.33(11) . . ? C15 C16 C21 112.18(10) . . ? C15 C16 C27 101.35(10) . . ? C21 C16 C27 110.80(10) . . ? C15 C16 C17 112.84(11) . . ? C21 C16 C17 111.29(11) . . ? C27 C16 C17 107.89(10) . . ? C18 C17 C16 118.88(11) . . ? C18 C17 C20 89.12(10) . . ? C16 C17 C20 118.16(12) . . ? C19 C18 C19A 22.6(3) . . ? C19 C18 C17 88.7(3) . . ? C19A C18 C17 89.1(3) . . ? C18 C19 C20 90.0(3) . . ? C20 C19A C18 90.8(4) . . ? C19A C20 C19 22.7(3) . . ? C19A C20 C17 90.0(3) . . ? C19 C20 C17 88.0(3) . . ? C22 C21 C26 118.05(12) . . ? C22 C21 C16 121.30(12) . . ? C26 C21 C16 120.45(12) . . ? C23 C22 C21 121.02(13) . . ? C24 C23 C22 120.01(14) . . ? C25 C24 C23 119.74(13) . . ? C24 C25 C26 120.24(13) . . ? C25 C26 C21 120.91(13) . . ? C9 C27 C28 125.06(12) . . ? C9 C27 C16 110.11(11) . . ? C28 C27 C16 124.77(11) . . ? C29 C28 C27 119.78(12) . . ? C29 C28 C33 121.59(12) . . ? C27 C28 C33 118.46(11) . . ? C28 C29 C30 134.19(13) . . ? C28 C29 C32 133.28(13) . . ? C30 C29 C32 91.47(11) . . ? C29 C30 C31 87.58(11) . . ? C30 C31 C32 89.16(11) . . ? C29 C32 C31 87.45(12) . . ? C38 C33 C34 118.20(13) . . ? C38 C33 C28 120.04(12) . . ? C34 C33 C28 121.76(12) . . ? C35 C34 C33 120.51(14) . . ? C36 C35 C34 120.39(15) . . ? C37 C36 C35 119.82(14) . . ? C36 C37 C38 120.02(14) . . ? C37 C38 C33 121.04(14) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.285 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.041 # Attachment 'chan26m.cif' data_chan26m _database_code_depnum_ccdc_archive 'CCDC 726883' #TrackingRef 'chan26m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H28 S2' _chemical_formula_sum 'C34 H28 S2' _chemical_formula_weight 500.68 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' S S 0.1246 0.1234 '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)/c 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 12.3446(6) _cell_length_b 20.3765(10) _cell_length_c 10.9971(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.298(2) _cell_angle_gamma 90.00 _cell_volume 2626.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6262 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 28.72 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9358 _exptl_absorpt_correction_T_max 0.9481 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _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 73291 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 30.80 _reflns_number_total 8201 _reflns_number_gt 5776 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1289P)^2^+1.4322P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8201 _refine_ls_number_parameters 354 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.2253 _refine_ls_wR_factor_gt 0.1917 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.052 _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 C1 C 0.28615(16) 0.62720(9) 0.72777(17) 0.0246(4) Uani 1 1 d . . . C2 C 0.3281(2) 0.68842(11) 0.7115(2) 0.0336(4) Uani 1 1 d . . . H2 H 0.3216 0.7243 0.7640 0.040 Uiso 1 1 calc R . . C3 C 0.3804(2) 0.69668(12) 0.6161(2) 0.0410(5) Uani 1 1 d . . . H3 H 0.4097 0.7384 0.6041 0.049 Uiso 1 1 calc R . . C4 C 0.3895(2) 0.64467(13) 0.5398(2) 0.0388(5) Uani 1 1 d . . . H4 H 0.4236 0.6514 0.4745 0.047 Uiso 1 1 calc R . . C5 C 0.34957(18) 0.58239(11) 0.55651(19) 0.0314(4) Uani 1 1 d . . . H5 H 0.3571 0.5466 0.5045 0.038 Uiso 1 1 calc R . . C6 C 0.29819(15) 0.57419(9) 0.65188(17) 0.0237(4) Uani 1 1 d . . . C7 C 0.25220(15) 0.51525(9) 0.69434(17) 0.0214(3) Uani 1 1 d . . . C8 C 0.25405(16) 0.45155(9) 0.64126(18) 0.0251(4) Uani 1 1 d . . . C9 C 0.25821(16) 0.39727(10) 0.60048(19) 0.0266(4) Uani 1 1 d . . . C10 C 0.26675(17) 0.33043(10) 0.56742(18) 0.0284(4) Uani 1 1 d . A . C11 C 0.2276(3) 0.27811(12) 0.6265(2) 0.0451(6) Uani 1 1 d D . . H11B H 0.1859 0.2802 0.6858 0.054 Uiso 0.338(5) 1 calc PR A 2 H11A H 0.1911 0.2864 0.6893 0.054 Uiso 0.662(5) 1 d PR A 1 C12 C 0.2417(7) 0.2176(4) 0.5922(7) 0.0523(16) Uani 0.662(5) 1 d PD A 1 H12 H 0.2186 0.1787 0.6248 0.063 Uiso 0.662(5) 1 calc PR A 1 C12A C 0.3418(8) 0.2463(5) 0.4655(9) 0.0387(19) Uani 0.338(5) 1 d PD A 2 H12A H 0.3846 0.2279 0.4156 0.046 Uiso 0.338(5) 1 calc PR A 2 C13 C 0.3176(2) 0.30807(13) 0.4790(2) 0.0435(6) Uani 1 1 d D . . H13B H 0.3361 0.3395 0.4249 0.052 Uiso 0.338(5) 1 calc PR A 2 H13A H 0.3504 0.3346 0.4287 0.052 Uiso 0.662(5) 1 d PR A 1 C14 C 0.21292(14) 0.53051(8) 0.79346(16) 0.0192(3) Uani 1 1 d . . . C15 C 0.15535(15) 0.48419(8) 0.85722(17) 0.0216(3) Uani 1 1 d . . . C16 C 0.05929(16) 0.45328(9) 0.78908(18) 0.0239(4) Uani 1 1 d . . . C17 C -0.01087(17) 0.45121(10) 0.6487(2) 0.0289(4) Uani 1 1 d . . . H17A H 0.0352 0.4517 0.5895 0.035 Uiso 1 1 calc R . . H17B H -0.0726 0.4843 0.6237 0.035 Uiso 1 1 calc R . . C18 C -0.0513(2) 0.38188(11) 0.6735(2) 0.0378(5) Uani 1 1 d . . . H18A H -0.1349 0.3756 0.6389 0.045 Uiso 1 1 calc R . . H18B H -0.0102 0.3456 0.6470 0.045 Uiso 1 1 calc R . . C19 C -0.00759(19) 0.39668(10) 0.8192(2) 0.0331(4) Uani 1 1 d . . . H19A H -0.0681 0.4102 0.8553 0.040 Uiso 1 1 calc R . . H19B H 0.0406 0.3615 0.8712 0.040 Uiso 1 1 calc R . . C20 C 0.20762(16) 0.47088(9) 0.99596(18) 0.0233(3) Uani 1 1 d . . . C21 C 0.32717(18) 0.46662(10) 1.05776(19) 0.0292(4) Uani 1 1 d . . . H21 H 0.3825 0.4720 1.0149 0.035 Uiso 1 1 calc R . . C22 C 0.35648(17) 0.45261(9) 1.1991(2) 0.0342(5) Uani 1 1 d . . . H22 H 0.4310 0.4472 1.2579 0.041 Uiso 1 1 calc R . . C23 C 0.14816(19) 0.46085(10) 1.0818(2) 0.0309(4) Uani 1 1 d . . . H23 H 0.0673 0.4609 1.0590 0.037 Uiso 1 1 calc R . . C24 C 0.22824(15) 0.60460(8) 0.82420(16) 0.0202(3) Uani 1 1 d . . . C25 C 0.10752(16) 0.63389(9) 0.79895(18) 0.0255(4) Uani 1 1 d . B . H25 H 0.0672 0.6095 0.8510 0.031 Uiso 1 1 calc R . . C26 C 0.0284(2) 0.63894(11) 0.6590(2) 0.0368(5) Uani 1 1 d . . . H26A H -0.0281 0.6030 0.6328 0.044 Uiso 0.54(2) 1 calc PR B 1 H26B H 0.0693 0.6455 0.5956 0.044 Uiso 0.54(2) 1 calc PR B 1 H26C H 0.0687 0.6344 0.5946 0.044 Uiso 0.46(2) 1 d PR B 2 H26D H -0.0387 0.6095 0.6391 0.044 Uiso 0.46(2) 1 d PR B 2 C27 C -0.0199(8) 0.7038(4) 0.6993(10) 0.048(2) Uani 0.54(2) 1 d PU B 1 H27A H -0.0306 0.7399 0.6364 0.057 Uiso 0.54(2) 1 calc PR B 1 H27B H -0.0891 0.6973 0.7251 0.057 Uiso 0.54(2) 1 calc PR B 1 C27A C 0.0256(14) 0.7131(4) 0.6724(9) 0.054(3) Uani 0.46(2) 1 d PU B 2 H27C H -0.0523 0.7310 0.6557 0.064 Uiso 0.46(2) 1 calc PR B 2 H27D H 0.0665 0.7368 0.6214 0.064 Uiso 0.46(2) 1 calc PR B 2 C28 C 0.0929(2) 0.70866(10) 0.8141(2) 0.0357(5) Uani 1 1 d . . . H28A H 0.1528 0.7358 0.7965 0.043 Uiso 0.54(2) 1 calc PR B 1 H28B H 0.0815 0.7213 0.8962 0.043 Uiso 0.54(2) 1 calc PR B 1 H28C H 0.0639 0.7202 0.8857 0.043 Uiso 0.46(2) 1 d PR B 2 H28D H 0.1616 0.7347 0.8179 0.043 Uiso 0.46(2) 1 d PR B 2 C29 C 0.30449(15) 0.61644(8) 0.96216(16) 0.0204(3) Uani 1 1 d . . . C30 C 0.42280(16) 0.61220(10) 0.99334(18) 0.0266(4) Uani 1 1 d . . . H30 H 0.4562 0.6061 0.9272 0.032 Uiso 1 1 calc R . . C31 C 0.49263(17) 0.61672(11) 1.1196(2) 0.0322(4) Uani 1 1 d . . . H31 H 0.5730 0.6130 1.1392 0.039 Uiso 1 1 calc R . . C32 C 0.44550(19) 0.62656(12) 1.2170(2) 0.0346(5) Uani 1 1 d . . . H32 H 0.4932 0.6291 1.3035 0.041 Uiso 1 1 calc R . . C33 C 0.32862(18) 0.63263(11) 1.18743(19) 0.0323(4) Uani 1 1 d . . . H33 H 0.2959 0.6400 1.2538 0.039 Uiso 1 1 calc R . . C34 C 0.25856(16) 0.62802(9) 1.06100(18) 0.0254(4) Uani 1 1 d . . . H34 H 0.1784 0.6328 1.0417 0.030 Uiso 1 1 calc R . . S1 S 0.31009(14) 0.22193(7) 0.47669(14) 0.0518(6) Uani 0.662(5) 1 d PD A 1 S1A S 0.2749(4) 0.20729(16) 0.5633(4) 0.0661(17) Uani 0.338(5) 1 d PD A 2 S2 S 0.23693(7) 0.44847(3) 1.23272(6) 0.0494(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0300(9) 0.0242(9) 0.0197(8) 0.0007(6) 0.0078(7) -0.0031(7) C2 0.0485(12) 0.0270(9) 0.0274(9) -0.0004(8) 0.0150(9) -0.0105(9) C3 0.0537(14) 0.0397(12) 0.0326(11) 0.0036(9) 0.0177(10) -0.0184(10) C4 0.0424(12) 0.0528(14) 0.0252(9) 0.0017(9) 0.0165(9) -0.0135(10) C5 0.0314(10) 0.0431(12) 0.0215(8) -0.0044(8) 0.0107(7) -0.0066(8) C6 0.0241(8) 0.0280(9) 0.0186(7) -0.0012(6) 0.0060(6) -0.0024(6) C7 0.0217(8) 0.0208(8) 0.0208(7) -0.0023(6) 0.0055(6) -0.0001(6) C8 0.0248(8) 0.0266(9) 0.0242(8) -0.0046(7) 0.0080(7) 0.0003(7) C9 0.0251(8) 0.0271(9) 0.0265(8) -0.0044(7) 0.0066(7) 0.0008(7) C10 0.0320(9) 0.0248(9) 0.0251(8) -0.0050(7) 0.0040(7) 0.0057(7) C11 0.0625(16) 0.0313(11) 0.0371(12) 0.0036(9) 0.0094(11) 0.0011(10) C12 0.079(4) 0.033(3) 0.043(3) 0.004(2) 0.016(3) 0.006(3) C12A 0.042(4) 0.029(4) 0.040(4) -0.006(4) 0.005(3) -0.001(3) C13 0.0528(14) 0.0386(12) 0.0374(12) -0.0094(9) 0.0119(10) 0.0172(10) C14 0.0203(7) 0.0181(7) 0.0183(7) -0.0001(6) 0.0049(6) 0.0005(6) C15 0.0258(8) 0.0175(7) 0.0232(8) 0.0008(6) 0.0103(7) 0.0020(6) C16 0.0273(9) 0.0197(8) 0.0263(8) 0.0001(6) 0.0107(7) -0.0016(6) C17 0.0274(9) 0.0275(9) 0.0292(9) -0.0008(7) 0.0053(7) -0.0028(7) C18 0.0363(11) 0.0324(11) 0.0404(12) -0.0020(9) 0.0060(9) -0.0120(8) C19 0.0346(10) 0.0275(10) 0.0391(11) 0.0017(8) 0.0144(9) -0.0079(8) C20 0.0311(9) 0.0169(7) 0.0238(8) 0.0010(6) 0.0113(7) 0.0029(6) C21 0.0330(10) 0.0254(9) 0.0280(9) 0.0010(7) 0.0078(8) 0.0038(7) C22 0.0254(9) 0.0163(8) 0.0499(12) -0.0050(8) -0.0041(8) 0.0051(6) C23 0.0372(10) 0.0296(10) 0.0287(9) 0.0041(8) 0.0145(8) 0.0044(8) C24 0.0252(8) 0.0171(7) 0.0193(7) -0.0007(6) 0.0083(6) -0.0005(6) C25 0.0281(9) 0.0199(8) 0.0265(8) -0.0033(7) 0.0057(7) 0.0033(6) C26 0.0366(11) 0.0325(11) 0.0322(10) -0.0040(8) -0.0022(8) 0.0066(8) C27 0.046(4) 0.029(3) 0.055(4) -0.005(2) -0.004(3) 0.013(3) C27A 0.065(7) 0.031(3) 0.049(4) 0.008(3) -0.006(4) 0.010(3) C28 0.0402(11) 0.0219(9) 0.0410(11) -0.0047(8) 0.0069(9) 0.0073(8) C29 0.0247(8) 0.0181(7) 0.0188(7) -0.0016(6) 0.0075(6) -0.0010(6) C30 0.0258(9) 0.0330(10) 0.0231(8) -0.0007(7) 0.0106(7) -0.0010(7) C31 0.0239(9) 0.0425(12) 0.0284(9) 0.0012(8) 0.0054(7) -0.0029(8) C32 0.0347(11) 0.0444(12) 0.0218(9) -0.0027(8) 0.0049(8) -0.0070(9) C33 0.0352(11) 0.0423(12) 0.0216(8) -0.0050(8) 0.0122(8) -0.0024(8) C34 0.0260(9) 0.0281(9) 0.0244(8) -0.0024(7) 0.0113(7) -0.0021(7) S1 0.0684(10) 0.0327(8) 0.0505(8) -0.0118(7) 0.0134(7) 0.0187(6) S1A 0.086(3) 0.0242(11) 0.068(3) -0.0003(13) -0.004(2) 0.0039(13) S2 0.0720(5) 0.0452(4) 0.0336(3) 0.0078(3) 0.0204(3) 0.0085(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 C1 C2 1.384(3) . ? C1 C6 1.401(3) . ? C1 C24 1.525(2) . ? C2 C3 1.403(3) . ? C3 C4 1.378(4) . ? C4 C5 1.394(3) . ? C5 C6 1.396(3) . ? C6 C7 1.466(3) . ? C7 C14 1.361(2) . ? C7 C8 1.426(2) . ? C8 C9 1.201(3) . ? C9 C10 1.422(3) . ? C10 C13 1.389(3) . ? C10 C11 1.411(3) . ? C11 C12 1.316(7) . ? C11 S1A 1.778(4) . ? C12 S1 1.734(6) . ? C12A C13 1.312(10) . ? C12A S1A 1.741(9) . ? C13 S1 1.757(3) . ? C14 C15 1.483(2) . ? C14 C24 1.546(2) . ? C15 C16 1.344(3) . ? C15 C20 1.483(2) . ? C16 C19 1.514(3) . ? C16 C17 1.515(3) . ? C17 C18 1.551(3) . ? C18 C19 1.551(3) . ? C20 C23 1.381(3) . ? C20 C21 1.420(3) . ? C21 C22 1.508(3) . ? C22 S2 1.632(3) . ? C23 S2 1.696(2) . ? C24 C29 1.533(2) . ? C24 C25 1.547(3) . ? C25 C26 1.545(3) . ? C25 C28 1.549(3) . ? C26 C27A 1.520(8) . ? C26 C27 1.570(7) . ? C27 C28 1.562(7) . ? C27A C28 1.521(8) . ? C29 C30 1.394(3) . ? C29 C34 1.395(2) . ? C30 C31 1.388(3) . ? C31 C32 1.384(3) . ? C32 C33 1.381(3) . ? C33 C34 1.391(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 C2 C1 C6 120.27(18) . . ? C2 C1 C24 129.70(18) . . ? C6 C1 C24 109.99(16) . . ? C1 C2 C3 118.9(2) . . ? C4 C3 C2 120.5(2) . . ? C3 C4 C5 121.32(19) . . ? C4 C5 C6 118.1(2) . . ? C5 C6 C1 120.90(18) . . ? C5 C6 C7 130.56(18) . . ? C1 C6 C7 108.53(15) . . ? C14 C7 C8 126.24(17) . . ? C14 C7 C6 109.82(15) . . ? C8 C7 C6 123.89(16) . . ? C9 C8 C7 177.8(2) . . ? C8 C9 C10 173.2(2) . . ? C13 C10 C11 111.7(2) . . ? C13 C10 C9 125.4(2) . . ? C11 C10 C9 122.8(2) . . ? C12 C11 C10 118.7(4) . . ? C12 C11 S1A 16.0(4) . . ? C10 C11 S1A 103.4(2) . . ? C11 C12 S1 107.6(5) . . ? C13 C12A S1A 101.5(6) . . ? C12A C13 C10 124.3(5) . . ? C12A C13 S1 18.9(4) . . ? C10 C13 S1 107.7(2) . . ? C7 C14 C15 125.27(16) . . ? C7 C14 C24 110.39(15) . . ? C15 C14 C24 124.19(14) . . ? C16 C15 C20 120.71(16) . . ? C16 C15 C14 120.29(16) . . ? C20 C15 C14 118.97(15) . . ? C15 C16 C19 132.94(18) . . ? C15 C16 C17 134.68(17) . . ? C19 C16 C17 91.44(15) . . ? C16 C17 C18 87.63(15) . . ? C19 C18 C17 88.73(15) . . ? C16 C19 C18 87.66(16) . . ? C23 C20 C21 111.06(18) . . ? C23 C20 C15 125.26(18) . . ? C21 C20 C15 123.68(17) . . ? C20 C21 C22 112.44(18) . . ? C21 C22 S2 107.56(14) . . ? C20 C23 S2 111.85(16) . . ? C1 C24 C29 111.38(14) . . ? C1 C24 C14 101.24(14) . . ? C29 C24 C14 111.42(14) . . ? C1 C24 C25 113.21(15) . . ? C29 C24 C25 111.99(14) . . ? C14 C24 C25 107.02(14) . . ? C26 C25 C24 118.43(16) . . ? C26 C25 C28 89.04(15) . . ? C24 C25 C28 119.89(17) . . ? C27A C26 C25 89.8(3) . . ? C27A C26 C27 27.6(4) . . ? C25 C26 C27 87.3(3) . . ? C28 C27 C26 87.7(4) . . ? C26 C27A C28 91.0(4) . . ? C27A C28 C25 89.6(3) . . ? C27A C28 C27 27.6(4) . . ? C25 C28 C27 87.4(3) . . ? C30 C29 C34 118.00(16) . . ? C30 C29 C24 120.27(15) . . ? C34 C29 C24 121.63(16) . . ? C31 C30 C29 121.02(17) . . ? C32 C31 C30 120.23(19) . . ? C33 C32 C31 119.51(19) . . ? C32 C33 C34 120.32(18) . . ? C33 C34 C29 120.87(17) . . ? C12 S1 C13 94.3(3) . . ? C12A S1A C11 98.5(4) . . ? C22 S2 C23 97.05(11) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.80 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.095 _refine_diff_density_min -0.833 _refine_diff_density_rms 0.105 # Attachment 'chan27o.cif' data_chan27o _database_code_depnum_ccdc_archive 'CCDC 726884' #TrackingRef 'chan27o.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H32' _chemical_formula_sum 'C38 H32' _chemical_formula_weight 488.64 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.1281(4) _cell_length_b 18.3334(6) _cell_length_c 19.8424(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5503.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7144 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 22.20 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9803 _exptl_absorpt_correction_T_max 0.9947 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _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 58764 _diffrn_reflns_av_R_equivalents 0.0691 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 26.81 _reflns_number_total 5873 _reflns_number_gt 3824 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1102P)^2^+3.3980P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5873 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1146 _refine_ls_R_factor_gt 0.0730 _refine_ls_wR_factor_ref 0.2103 _refine_ls_wR_factor_gt 0.1831 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 C1 C 0.31144(17) -0.11409(15) 0.31724(15) 0.0353(6) Uani 1 1 d . . . H1 H 0.3104 -0.1048 0.2701 0.042 Uiso 1 1 calc R . . C2 C 0.25339(18) -0.16479(16) 0.34509(17) 0.0420(7) Uani 1 1 d . . . H2 H 0.2140 -0.1909 0.3167 0.050 Uiso 1 1 calc R . . C3 C 0.2527(2) -0.17732(16) 0.41324(18) 0.0471(8) Uani 1 1 d . . . H3 H 0.2129 -0.2118 0.4320 0.057 Uiso 1 1 calc R . . C4 C 0.3101(2) -0.13958(18) 0.45418(17) 0.0536(9) Uani 1 1 d . . . H4 H 0.3093 -0.1479 0.5014 0.064 Uiso 1 1 calc R . . C5 C 0.3690(2) -0.08949(17) 0.42715(15) 0.0443(8) Uani 1 1 d . . . H5 H 0.4082 -0.0637 0.4559 0.053 Uiso 1 1 calc R . . C6 C 0.37080(16) -0.07708(13) 0.35824(13) 0.0276(6) Uani 1 1 d . . . C7 C 0.43478(15) -0.02827(13) 0.32971(13) 0.0265(5) Uani 1 1 d . . . C8 C 0.49097(15) 0.01011(13) 0.30650(12) 0.0255(5) Uani 1 1 d . . . C9 C 0.56079(15) 0.05641(13) 0.27703(12) 0.0229(5) Uani 1 1 d . . . C10 C 0.56635(14) 0.04293(13) 0.20142(12) 0.0246(5) Uani 1 1 d . . . C11 C 0.58566(17) -0.02057(15) 0.16707(13) 0.0335(6) Uani 1 1 d . . . H11 H 0.5971 -0.0647 0.1907 0.040 Uiso 1 1 calc R . . C12 C 0.58790(19) -0.01835(16) 0.09698(14) 0.0403(7) Uani 1 1 d . . . H12 H 0.6020 -0.0613 0.0725 0.048 Uiso 1 1 calc R . . C13 C 0.56987(17) 0.04546(17) 0.06242(13) 0.0377(7) Uani 1 1 d . . . H13 H 0.5713 0.0455 0.0146 0.045 Uiso 1 1 calc R . . C14 C 0.54963(15) 0.10952(15) 0.09662(13) 0.0302(6) Uani 1 1 d . . . H14 H 0.5374 0.1533 0.0728 0.036 Uiso 1 1 calc R . . C15 C 0.54779(14) 0.10779(13) 0.16686(12) 0.0237(5) Uani 1 1 d . . . C16 C 0.52896(14) 0.16572(13) 0.21603(11) 0.0222(5) Uani 1 1 d . . . C17 C 0.50577(15) 0.24098(13) 0.19268(12) 0.0261(5) Uani 1 1 d . . . H17 H 0.5575 0.2624 0.1683 0.031 Uiso 1 1 calc R . . C18 C 0.46603(17) 0.29917(14) 0.23996(13) 0.0320(6) Uani 1 1 d . . . H18A H 0.4341 0.2786 0.2792 0.038 Uiso 1 1 calc R . . H18B H 0.5088 0.3370 0.2543 0.038 Uiso 1 1 calc R . . C19 C 0.40499(18) 0.32330(15) 0.18196(15) 0.0383(7) Uani 1 1 d . . . H19A H 0.3429 0.3313 0.1958 0.046 Uiso 1 1 calc R . . H19B H 0.4278 0.3654 0.1559 0.046 Uiso 1 1 calc R . . C20 C 0.42138(19) 0.24910(16) 0.14807(16) 0.0406(7) Uani 1 1 d . . . H20A H 0.4338 0.2523 0.0992 0.049 Uiso 1 1 calc R . . H20B H 0.3751 0.2123 0.1575 0.049 Uiso 1 1 calc R . . C21 C 0.53450(14) 0.13882(13) 0.27909(11) 0.0218(5) Uani 1 1 d . . . C22 C 0.52328(14) 0.17737(12) 0.34415(11) 0.0221(5) Uani 1 1 d . . . C23 C 0.58298(15) 0.22589(14) 0.36395(12) 0.0269(5) Uani 1 1 d . . . C24 C 0.5873(2) 0.28289(16) 0.41957(14) 0.0413(7) Uani 1 1 d . . . H24A H 0.6093 0.2639 0.4632 0.050 Uiso 1 1 calc R . . H24B H 0.5319 0.3108 0.4256 0.050 Uiso 1 1 calc R . . C25 C 0.6578(3) 0.3228(2) 0.37763(18) 0.0680(11) Uani 1 1 d . . . H25A H 0.7124 0.3341 0.4031 0.082 Uiso 1 1 calc R . . H25B H 0.6352 0.3666 0.3542 0.082 Uiso 1 1 calc R . . C26 C 0.66617(17) 0.25534(17) 0.33167(15) 0.0399(7) Uani 1 1 d . . . H26A H 0.6599 0.2663 0.2830 0.048 Uiso 1 1 calc R . . H26B H 0.7195 0.2255 0.3404 0.048 Uiso 1 1 calc R . . C27 C 0.44276(15) 0.16076(13) 0.38468(12) 0.0246(5) Uani 1 1 d . . . C28 C 0.36176(15) 0.14905(14) 0.35288(13) 0.0274(6) Uani 1 1 d . . . H28 H 0.3582 0.1520 0.3052 0.033 Uiso 1 1 calc R . . C29 C 0.28612(17) 0.13310(15) 0.38997(13) 0.0341(6) Uani 1 1 d . . . H29 H 0.2315 0.1252 0.3675 0.041 Uiso 1 1 calc R . . C30 C 0.29025(19) 0.12875(16) 0.45900(14) 0.0399(7) Uani 1 1 d . . . H30 H 0.2386 0.1180 0.4843 0.048 Uiso 1 1 calc R . . C31 C 0.3699(2) 0.14008(17) 0.49141(14) 0.0436(7) Uani 1 1 d . . . H31 H 0.3731 0.1368 0.5391 0.052 Uiso 1 1 calc R . . C32 C 0.44536(18) 0.15625(15) 0.45453(13) 0.0362(6) Uani 1 1 d . . . H32 H 0.4996 0.1644 0.4774 0.043 Uiso 1 1 calc R . . C33 C 0.64923(15) 0.04523(13) 0.31390(12) 0.0237(5) Uani 1 1 d . . . C34 C 0.65202(18) 0.02701(16) 0.38163(13) 0.0356(6) Uani 1 1 d . . . H34 H 0.5985 0.0190 0.4055 0.043 Uiso 1 1 calc R . . C35 C 0.73218(19) 0.02041(17) 0.41483(15) 0.0426(7) Uani 1 1 d . . . H35 H 0.7329 0.0076 0.4612 0.051 Uiso 1 1 calc R . . C36 C 0.81041(18) 0.03206(15) 0.38185(14) 0.0356(6) Uani 1 1 d . . . H36 H 0.8651 0.0280 0.4050 0.043 Uiso 1 1 calc R . . C37 C 0.80825(17) 0.04981(18) 0.31450(15) 0.0422(7) Uani 1 1 d . . . H37 H 0.8620 0.0577 0.2908 0.051 Uiso 1 1 calc R . . C38 C 0.72875(17) 0.05631(17) 0.28108(14) 0.0400(7) Uani 1 1 d . . . H38 H 0.7286 0.0686 0.2346 0.048 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 C1 0.0277(13) 0.0358(15) 0.0425(16) -0.0009(12) 0.0009(12) -0.0043(11) C2 0.0278(14) 0.0380(16) 0.060(2) -0.0062(14) -0.0002(13) -0.0090(12) C3 0.0376(16) 0.0329(16) 0.071(2) 0.0039(15) 0.0135(15) -0.0090(13) C4 0.067(2) 0.0481(19) 0.0461(19) 0.0114(15) 0.0082(16) -0.0123(17) C5 0.0498(18) 0.0428(17) 0.0404(17) 0.0068(13) -0.0047(14) -0.0152(14) C6 0.0226(12) 0.0224(13) 0.0377(14) 0.0009(11) 0.0017(10) -0.0013(10) C7 0.0214(12) 0.0247(12) 0.0334(14) -0.0004(10) -0.0012(10) 0.0030(10) C8 0.0222(12) 0.0248(12) 0.0296(13) 0.0015(10) -0.0009(10) 0.0025(10) C9 0.0184(11) 0.0245(12) 0.0258(12) 0.0006(10) 0.0023(9) -0.0002(9) C10 0.0163(11) 0.0298(13) 0.0277(13) -0.0007(10) -0.0024(9) -0.0026(9) C11 0.0320(14) 0.0324(14) 0.0361(15) -0.0054(11) 0.0019(11) 0.0035(11) C12 0.0377(16) 0.0419(17) 0.0413(17) -0.0164(13) 0.0019(13) 0.0021(13) C13 0.0296(14) 0.0575(19) 0.0261(14) -0.0107(13) 0.0010(11) -0.0043(13) C14 0.0208(12) 0.0405(15) 0.0293(14) 0.0017(11) -0.0007(10) -0.0013(11) C15 0.0145(11) 0.0297(13) 0.0268(13) -0.0024(10) -0.0015(9) -0.0022(9) C16 0.0139(10) 0.0280(13) 0.0248(12) 0.0011(10) 0.0005(9) -0.0019(9) C17 0.0230(12) 0.0277(13) 0.0275(12) 0.0025(10) -0.0037(10) -0.0029(10) C18 0.0314(14) 0.0288(14) 0.0357(14) 0.0028(11) -0.0047(11) 0.0039(11) C19 0.0324(14) 0.0315(14) 0.0510(17) 0.0053(13) -0.0118(13) 0.0024(12) C20 0.0425(16) 0.0341(15) 0.0454(17) 0.0041(13) -0.0213(13) 0.0041(13) C21 0.0153(10) 0.0238(12) 0.0262(12) 0.0018(10) 0.0001(9) -0.0011(9) C22 0.0191(11) 0.0240(12) 0.0233(12) 0.0009(9) 0.0005(9) 0.0012(9) C23 0.0197(11) 0.0343(14) 0.0267(13) -0.0013(10) -0.0007(10) -0.0025(10) C24 0.0442(16) 0.0453(17) 0.0344(15) -0.0092(13) -0.0048(13) -0.0116(14) C25 0.079(3) 0.073(3) 0.052(2) -0.0209(18) 0.0119(18) -0.046(2) C26 0.0249(13) 0.0502(18) 0.0445(17) -0.0041(14) 0.0000(12) -0.0134(12) C27 0.0252(12) 0.0237(12) 0.0249(12) -0.0005(10) 0.0009(10) -0.0009(10) C28 0.0246(12) 0.0324(14) 0.0253(13) -0.0017(11) 0.0024(10) -0.0011(10) C29 0.0245(13) 0.0423(16) 0.0355(15) -0.0099(12) 0.0058(11) -0.0051(11) C30 0.0385(16) 0.0490(17) 0.0323(15) -0.0058(13) 0.0140(12) -0.0145(13) C31 0.0495(17) 0.0580(19) 0.0233(14) 0.0002(13) 0.0072(13) -0.0178(15) C32 0.0360(15) 0.0457(16) 0.0269(14) 0.0014(12) -0.0018(11) -0.0109(12) C33 0.0226(12) 0.0218(12) 0.0266(13) 0.0029(10) -0.0013(10) 0.0010(9) C34 0.0290(14) 0.0473(17) 0.0305(14) 0.0092(12) 0.0014(11) -0.0055(12) C35 0.0397(16) 0.0559(19) 0.0322(15) 0.0138(14) -0.0051(12) -0.0039(14) C36 0.0285(14) 0.0385(15) 0.0398(16) 0.0043(12) -0.0119(12) 0.0008(12) C37 0.0198(13) 0.065(2) 0.0415(16) 0.0076(15) 0.0015(11) -0.0001(13) C38 0.0264(14) 0.065(2) 0.0291(14) 0.0110(14) 0.0007(11) 0.0007(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.389(4) . ? C1 C2 1.393(4) . ? C2 C3 1.372(5) . ? C3 C4 1.375(5) . ? C4 C5 1.388(4) . ? C5 C6 1.386(4) . ? C6 C7 1.435(3) . ? C7 C8 1.196(3) . ? C8 C9 1.476(3) . ? C9 C10 1.523(3) . ? C9 C33 1.539(3) . ? C9 C21 1.563(3) . ? C10 C11 1.380(3) . ? C10 C15 1.401(3) . ? C11 C12 1.392(4) . ? C12 C13 1.383(4) . ? C13 C14 1.391(4) . ? C14 C15 1.394(3) . ? C15 C16 1.470(3) . ? C16 C21 1.347(3) . ? C16 C17 1.497(3) . ? C17 C18 1.543(3) . ? C17 C20 1.561(3) . ? C18 C19 1.540(4) . ? C19 C20 1.538(4) . ? C21 C22 1.482(3) . ? C22 C23 1.327(3) . ? C22 C27 1.491(3) . ? C23 C26 1.512(3) . ? C23 C24 1.521(4) . ? C24 C25 1.538(4) . ? C25 C26 1.541(4) . ? C27 C32 1.389(3) . ? C27 C28 1.395(3) . ? C28 C29 1.392(3) . ? C29 C30 1.373(4) . ? C30 C31 1.382(4) . ? C31 C32 1.387(4) . ? C33 C38 1.383(3) . ? C33 C34 1.385(3) . ? C34 C35 1.385(4) . ? C35 C36 1.369(4) . ? C36 C37 1.376(4) . ? C37 C38 1.379(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 C6 C1 C2 120.1(3) . . ? C3 C2 C1 120.5(3) . . ? C2 C3 C4 119.6(3) . . ? C3 C4 C5 120.7(3) . . ? C6 C5 C4 120.1(3) . . ? C5 C6 C1 119.0(2) . . ? C5 C6 C7 120.3(2) . . ? C1 C6 C7 120.6(2) . . ? C8 C7 C6 177.1(3) . . ? C7 C8 C9 179.0(3) . . ? C8 C9 C10 109.66(19) . . ? C8 C9 C33 110.94(19) . . ? C10 C9 C33 113.50(18) . . ? C8 C9 C21 111.32(19) . . ? C10 C9 C21 101.34(18) . . ? C33 C9 C21 109.74(18) . . ? C11 C10 C15 121.1(2) . . ? C11 C10 C9 129.4(2) . . ? C15 C10 C9 109.5(2) . . ? C10 C11 C12 118.3(3) . . ? C13 C12 C11 121.0(3) . . ? C12 C13 C14 121.1(2) . . ? C13 C14 C15 118.2(3) . . ? C14 C15 C10 120.3(2) . . ? C14 C15 C16 130.6(2) . . ? C10 C15 C16 109.1(2) . . ? C21 C16 C15 109.9(2) . . ? C21 C16 C17 129.7(2) . . ? C15 C16 C17 120.4(2) . . ? C16 C17 C18 122.7(2) . . ? C16 C17 C20 117.1(2) . . ? C18 C17 C20 87.72(19) . . ? C19 C18 C17 88.73(19) . . ? C20 C19 C18 88.63(19) . . ? C19 C20 C17 88.2(2) . . ? C16 C21 C22 128.9(2) . . ? C16 C21 C9 110.2(2) . . ? C22 C21 C9 120.87(19) . . ? C23 C22 C21 120.0(2) . . ? C23 C22 C27 122.2(2) . . ? C21 C22 C27 117.78(19) . . ? C22 C23 C26 132.9(2) . . ? C22 C23 C24 134.8(2) . . ? C26 C23 C24 91.5(2) . . ? C23 C24 C25 87.9(2) . . ? C24 C25 C26 89.8(2) . . ? C23 C26 C25 88.1(2) . . ? C32 C27 C28 117.8(2) . . ? C32 C27 C22 121.8(2) . . ? C28 C27 C22 120.3(2) . . ? C29 C28 C27 121.0(2) . . ? C30 C29 C28 120.2(2) . . ? C29 C30 C31 119.7(2) . . ? C30 C31 C32 120.3(3) . . ? C31 C32 C27 121.0(3) . . ? C38 C33 C34 117.8(2) . . ? C38 C33 C9 120.9(2) . . ? C34 C33 C9 121.3(2) . . ? C33 C34 C35 120.6(2) . . ? C36 C35 C34 121.0(3) . . ? C35 C36 C37 118.7(2) . . ? C36 C37 C38 120.6(2) . . ? C37 C38 C33 121.3(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.81 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.480 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.076 # Attachment 'chan30.cif' data_chan30 _database_code_depnum_ccdc_archive 'CCDC 726885' #TrackingRef 'chan30.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H44 O2' _chemical_formula_sum 'C50 H44 O2' _chemical_formula_weight 676.85 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3273(3) _cell_length_b 14.4418(4) _cell_length_c 14.7088(4) _cell_angle_alpha 66.882(2) _cell_angle_beta 70.6770(10) _cell_angle_gamma 82.3190(10) _cell_volume 1903.91(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7702 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.67 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9793 _exptl_absorpt_correction_T_max 0.9930 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _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 49312 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 29.11 _reflns_number_total 10178 _reflns_number_gt 6559 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0886P)^2^+0.0837P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10178 _refine_ls_number_parameters 472 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0903 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1673 _refine_ls_wR_factor_gt 0.1333 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 C1 C 0.5607(3) -0.13537(17) 1.45520(15) 0.0597(6) Uani 1 1 d . . . H1A H 0.4703 -0.1662 1.4960 0.090 Uiso 1 1 calc R . . H1B H 0.5957 -0.1134 1.4978 0.090 Uiso 1 1 calc R . . H1C H 0.6242 -0.1847 1.4330 0.090 Uiso 1 1 calc R . . C2 C 0.5484(2) -0.04654(14) 1.36182(14) 0.0446(5) Uani 1 1 d . . . H2A H 0.4828 0.0031 1.3833 0.054 Uiso 1 1 calc R . . H2B H 0.6387 -0.0135 1.3211 0.054 Uiso 1 1 calc R . . C3 C 0.45484(17) -0.01362(12) 1.22273(12) 0.0294(3) Uani 1 1 d . . . C4 C 0.40793(17) -0.05481(12) 1.16838(12) 0.0320(4) Uani 1 1 d . . . H4 H 0.4129 -0.1256 1.1855 0.038 Uiso 1 1 calc R . . C5 C 0.35418(17) 0.00585(11) 1.08978(12) 0.0293(3) Uani 1 1 d . . . H5 H 0.3222 -0.0225 1.0528 0.035 Uiso 1 1 calc R . . C6 C 0.34785(16) 0.10927(11) 1.06606(11) 0.0249(3) Uani 1 1 d . . . C7 C 0.39550(15) 0.15025(11) 1.11971(11) 0.0234(3) Uani 1 1 d . . . C8 C 0.45007(16) 0.09005(11) 1.19848(12) 0.0275(3) Uani 1 1 d . . . H8 H 0.4831 0.1186 1.2348 0.033 Uiso 1 1 calc R . . C9 C 0.29840(15) 0.19100(11) 0.98713(11) 0.0243(3) Uani 1 1 d . . . C10 C 0.31422(15) 0.28176(11) 0.99195(11) 0.0235(3) Uani 1 1 d . . . C11 C 0.37067(15) 0.26364(11) 1.08233(11) 0.0227(3) Uani 1 1 d . . . C12 C 0.23956(16) 0.16896(11) 0.92308(12) 0.0274(3) Uani 1 1 d . . . C13 C 0.18870(17) 0.13809(12) 0.87810(12) 0.0292(3) Uani 1 1 d . . . C14 C 0.12833(16) 0.10566(12) 0.82097(12) 0.0268(3) Uani 1 1 d . . . C15 C 0.07175(17) 0.00967(11) 0.86250(12) 0.0300(4) Uani 1 1 d . . . H15 H 0.0740 -0.0355 0.9295 0.036 Uiso 1 1 calc R . . C16 C 0.01239(17) -0.02008(12) 0.80652(13) 0.0327(4) Uani 1 1 d . . . H16 H -0.0274 -0.0851 0.8366 0.039 Uiso 1 1 calc R . . C17 C 0.00968(17) 0.04277(12) 0.70769(13) 0.0308(4) Uani 1 1 d . . . C18 C -0.0533(2) 0.00840(15) 0.64738(16) 0.0479(5) Uani 1 1 d . . . H18A H -0.1534 0.0076 0.6769 0.072 Uiso 1 1 calc R . . H18B H -0.0202 -0.0595 0.6514 0.072 Uiso 1 1 calc R . . H18C H -0.0271 0.0547 0.5746 0.072 Uiso 1 1 calc R . . C19 C 0.06567(18) 0.13814(13) 0.66680(13) 0.0345(4) Uani 1 1 d . . . H19 H 0.0647 0.1826 0.5993 0.041 Uiso 1 1 calc R . . C20 C 0.12292(17) 0.16983(12) 0.72260(12) 0.0319(4) Uani 1 1 d . . . H20 H 0.1589 0.2360 0.6935 0.038 Uiso 1 1 calc R . . C21 C 0.28753(15) 0.38202(11) 0.92274(11) 0.0245(3) Uani 1 1 d . . . C22 C 0.26750(16) 0.46135(11) 0.95348(11) 0.0256(3) Uani 1 1 d . . . H22 H 0.2588 0.4450 1.0244 0.031 Uiso 1 1 calc R . . C23 C 0.25738(16) 0.56902(11) 0.89230(11) 0.0262(3) Uani 1 1 d . . . C24 C 0.33519(17) 0.61461(12) 0.78814(12) 0.0314(4) Uani 1 1 d . . . H24 H 0.3919 0.5747 0.7520 0.038 Uiso 1 1 calc R . . C25 C 0.32929(19) 0.71847(13) 0.73770(14) 0.0401(4) Uani 1 1 d . . . H25 H 0.3829 0.7490 0.6672 0.048 Uiso 1 1 calc R . . C26 C 0.2465(2) 0.77786(13) 0.78861(16) 0.0427(5) Uani 1 1 d . . . H26 H 0.2426 0.8486 0.7531 0.051 Uiso 1 1 calc R . . C27 C 0.16972(19) 0.73367(13) 0.89122(15) 0.0390(4) Uani 1 1 d . . . H27 H 0.1126 0.7740 0.9266 0.047 Uiso 1 1 calc R . . C28 C 0.17582(17) 0.63072(12) 0.94257(13) 0.0313(4) Uani 1 1 d . . . H28 H 0.1235 0.6012 1.0136 0.038 Uiso 1 1 calc R . . C29 C 0.28412(16) 0.39499(11) 0.81785(11) 0.0261(3) Uani 1 1 d . . . C30 C 0.39481(18) 0.36745(12) 0.74857(12) 0.0336(4) Uani 1 1 d . . . H30 H 0.4739 0.3380 0.7686 0.040 Uiso 1 1 calc R . . C31 C 0.3907(2) 0.38269(13) 0.65037(13) 0.0413(4) Uani 1 1 d . . . H31 H 0.4677 0.3639 0.6038 0.050 Uiso 1 1 calc R . . C32 C 0.2766(2) 0.42481(13) 0.61880(13) 0.0413(5) Uani 1 1 d . . . C33 C 0.2720(3) 0.43720(17) 0.51265(15) 0.0646(7) Uani 1 1 d . . . H33A H 0.1872 0.4723 0.5016 0.097 Uiso 1 1 calc R . . H33B H 0.2745 0.3708 0.5087 0.097 Uiso 1 1 calc R . . H33C H 0.3513 0.4766 0.4590 0.097 Uiso 1 1 calc R . . C34 C 0.1657(2) 0.45168(13) 0.68855(14) 0.0395(4) Uani 1 1 d . . . H34 H 0.0863 0.4804 0.6687 0.047 Uiso 1 1 calc R . . C35 C 0.16922(17) 0.43734(12) 0.78607(12) 0.0317(4) Uani 1 1 d . . . H35 H 0.0923 0.4566 0.8323 0.038 Uiso 1 1 calc R . . C36 C 0.50315(15) 0.32434(11) 1.04770(11) 0.0244(3) Uani 1 1 d . . . H36A H 0.4764 0.3947 1.0403 0.029 Uiso 1 1 calc R . . H36B H 0.5465 0.2964 1.1039 0.029 Uiso 1 1 calc R . . C37 C 0.60929(16) 0.32585(11) 0.94805(12) 0.0262(3) Uani 1 1 d . . . C38 C 0.64597(18) 0.41655(12) 0.86414(12) 0.0331(4) Uani 1 1 d . . . H38 H 0.5979 0.4764 0.8682 0.040 Uiso 1 1 calc R . . C39 C 0.7514(2) 0.42122(14) 0.77461(13) 0.0420(4) Uani 1 1 d . . . H39 H 0.7755 0.4839 0.7183 0.050 Uiso 1 1 calc R . . C40 C 0.8216(2) 0.33445(15) 0.76732(14) 0.0435(5) Uani 1 1 d . . . H40 H 0.8944 0.3373 0.7064 0.052 Uiso 1 1 calc R . . C41 C 0.78481(19) 0.24381(14) 0.84933(14) 0.0419(4) Uani 1 1 d . . . H41 H 0.8316 0.1839 0.8443 0.050 Uiso 1 1 calc R . . C42 C 0.68082(17) 0.23955(12) 0.93840(13) 0.0330(4) Uani 1 1 d . . . H42 H 0.6574 0.1766 0.9943 0.040 Uiso 1 1 calc R . . C43 C 0.26162(15) 0.28271(11) 1.17432(11) 0.0228(3) Uani 1 1 d . . . C44 C 0.29779(17) 0.29079(12) 1.25439(12) 0.0294(3) Uani 1 1 d . . . H44 H 0.3921 0.2923 1.2481 0.035 Uiso 1 1 calc R . . C45 C 0.19952(17) 0.29670(12) 1.34247(12) 0.0308(4) Uani 1 1 d . . . H45 H 0.2268 0.3015 1.3961 0.037 Uiso 1 1 calc R . . C46 C 0.06130(16) 0.29567(11) 1.35286(11) 0.0277(3) Uani 1 1 d . . . C47 C 0.02284(16) 0.29075(12) 1.27318(12) 0.0305(4) Uani 1 1 d . . . H47 H -0.0715 0.2923 1.2783 0.037 Uiso 1 1 calc R . . C48 C 0.12250(16) 0.28353(12) 1.18610(12) 0.0281(3) Uani 1 1 d . . . H48 H 0.0948 0.2790 1.1325 0.034 Uiso 1 1 calc R . . C49 C -0.17040(17) 0.27529(14) 1.46639(13) 0.0359(4) Uani 1 1 d . . . H49A H -0.1752 0.2110 1.4584 0.043 Uiso 1 1 calc R . . H49B H -0.2131 0.3288 1.4181 0.043 Uiso 1 1 calc R . . C50 C -0.2441(2) 0.26615(15) 1.57597(14) 0.0448(5) Uani 1 1 d . . . H50A H -0.1977 0.2159 1.6226 0.067 Uiso 1 1 calc R . . H50B H -0.3390 0.2452 1.5952 0.067 Uiso 1 1 calc R . . H50C H -0.2440 0.3314 1.5819 0.067 Uiso 1 1 calc R . . O1 O 0.50121(13) -0.08184(8) 1.30116(9) 0.0381(3) Uani 1 1 d . . . O2 O -0.02954(11) 0.30003(9) 1.44372(8) 0.0350(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0688(15) 0.0647(14) 0.0356(10) -0.0044(10) -0.0217(10) 0.0017(12) C2 0.0583(13) 0.0404(10) 0.0374(10) -0.0112(8) -0.0242(9) 0.0068(9) C3 0.0309(8) 0.0272(8) 0.0246(7) -0.0046(6) -0.0078(7) -0.0005(7) C4 0.0378(9) 0.0219(7) 0.0329(8) -0.0081(6) -0.0078(7) -0.0030(7) C5 0.0346(9) 0.0269(8) 0.0288(8) -0.0121(6) -0.0087(7) -0.0050(7) C6 0.0258(8) 0.0253(7) 0.0244(7) -0.0101(6) -0.0066(6) -0.0028(6) C7 0.0226(7) 0.0245(7) 0.0235(7) -0.0100(6) -0.0055(6) -0.0017(6) C8 0.0293(8) 0.0267(8) 0.0290(8) -0.0105(6) -0.0115(7) -0.0016(6) C9 0.0253(8) 0.0264(7) 0.0242(7) -0.0111(6) -0.0082(6) -0.0022(6) C10 0.0239(7) 0.0271(7) 0.0223(7) -0.0108(6) -0.0081(6) -0.0014(6) C11 0.0246(7) 0.0235(7) 0.0234(7) -0.0098(6) -0.0100(6) -0.0010(6) C12 0.0306(8) 0.0257(8) 0.0283(8) -0.0109(6) -0.0101(7) -0.0021(6) C13 0.0325(9) 0.0283(8) 0.0295(8) -0.0120(6) -0.0110(7) -0.0015(7) C14 0.0277(8) 0.0306(8) 0.0291(8) -0.0169(6) -0.0107(6) 0.0007(6) C15 0.0381(9) 0.0267(8) 0.0290(8) -0.0108(6) -0.0150(7) 0.0010(7) C16 0.0361(9) 0.0270(8) 0.0419(9) -0.0164(7) -0.0155(8) -0.0017(7) C17 0.0306(9) 0.0354(9) 0.0369(9) -0.0217(7) -0.0146(7) 0.0027(7) C18 0.0540(12) 0.0540(12) 0.0574(12) -0.0308(10) -0.0322(10) 0.0008(9) C19 0.0386(10) 0.0392(9) 0.0294(8) -0.0123(7) -0.0153(7) -0.0005(8) C20 0.0376(9) 0.0294(8) 0.0310(8) -0.0108(7) -0.0118(7) -0.0057(7) C21 0.0238(7) 0.0266(7) 0.0247(7) -0.0095(6) -0.0087(6) -0.0019(6) C22 0.0291(8) 0.0262(7) 0.0231(7) -0.0087(6) -0.0099(6) -0.0016(6) C23 0.0280(8) 0.0252(7) 0.0298(8) -0.0091(6) -0.0143(7) -0.0031(6) C24 0.0304(9) 0.0331(9) 0.0334(8) -0.0103(7) -0.0133(7) -0.0056(7) C25 0.0405(10) 0.0395(10) 0.0367(9) 0.0018(8) -0.0209(8) -0.0154(8) C26 0.0470(11) 0.0256(8) 0.0628(12) -0.0078(8) -0.0357(10) -0.0017(8) C27 0.0401(10) 0.0303(9) 0.0592(12) -0.0199(8) -0.0296(9) 0.0068(7) C28 0.0311(9) 0.0313(8) 0.0383(9) -0.0149(7) -0.0174(7) 0.0013(7) C29 0.0321(8) 0.0244(7) 0.0252(7) -0.0085(6) -0.0123(7) -0.0041(6) C30 0.0395(10) 0.0341(9) 0.0309(8) -0.0140(7) -0.0135(7) 0.0010(7) C31 0.0539(12) 0.0405(10) 0.0292(9) -0.0157(8) -0.0072(8) -0.0051(9) C32 0.0692(13) 0.0308(9) 0.0283(8) -0.0051(7) -0.0224(9) -0.0137(9) C33 0.117(2) 0.0501(12) 0.0380(11) -0.0089(9) -0.0400(13) -0.0168(13) C34 0.0516(11) 0.0324(9) 0.0421(10) -0.0060(7) -0.0310(9) -0.0063(8) C35 0.0333(9) 0.0312(8) 0.0329(8) -0.0093(7) -0.0148(7) -0.0032(7) C36 0.0261(8) 0.0247(7) 0.0272(7) -0.0122(6) -0.0105(6) -0.0017(6) C37 0.0251(8) 0.0297(8) 0.0296(8) -0.0142(6) -0.0105(6) -0.0033(6) C38 0.0361(9) 0.0317(9) 0.0323(8) -0.0121(7) -0.0106(7) -0.0013(7) C39 0.0443(11) 0.0440(10) 0.0310(9) -0.0100(8) -0.0038(8) -0.0109(9) C40 0.0398(10) 0.0524(11) 0.0383(10) -0.0257(9) 0.0034(8) -0.0115(9) C41 0.0362(10) 0.0399(10) 0.0517(11) -0.0275(9) -0.0020(9) -0.0042(8) C42 0.0308(9) 0.0294(8) 0.0384(9) -0.0156(7) -0.0046(7) -0.0049(7) C43 0.0257(8) 0.0225(7) 0.0219(7) -0.0083(6) -0.0092(6) -0.0008(6) C44 0.0257(8) 0.0390(9) 0.0301(8) -0.0165(7) -0.0121(7) -0.0006(7) C45 0.0330(9) 0.0405(9) 0.0262(8) -0.0159(7) -0.0133(7) -0.0014(7) C46 0.0286(8) 0.0299(8) 0.0245(7) -0.0104(6) -0.0072(6) -0.0011(6) C47 0.0240(8) 0.0401(9) 0.0305(8) -0.0144(7) -0.0098(7) -0.0027(7) C48 0.0283(8) 0.0342(8) 0.0263(8) -0.0122(6) -0.0120(7) -0.0020(6) C49 0.0292(9) 0.0433(10) 0.0342(9) -0.0141(8) -0.0080(7) -0.0024(7) C50 0.0367(10) 0.0530(11) 0.0393(10) -0.0199(9) -0.0016(8) -0.0001(9) O1 0.0484(8) 0.0299(6) 0.0341(6) -0.0040(5) -0.0202(6) 0.0010(5) O2 0.0292(6) 0.0494(7) 0.0277(6) -0.0181(5) -0.0052(5) -0.0022(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.496(3) . ? C2 O1 1.416(2) . ? C3 O1 1.3704(19) . ? C3 C4 1.391(2) . ? C3 C8 1.394(2) . ? C4 C5 1.383(2) . ? C5 C6 1.391(2) . ? C6 C7 1.384(2) . ? C6 C9 1.469(2) . ? C7 C8 1.388(2) . ? C7 C11 1.524(2) . ? C9 C10 1.374(2) . ? C9 C12 1.423(2) . ? C10 C21 1.460(2) . ? C10 C11 1.541(2) . ? C11 C43 1.542(2) . ? C11 C36 1.552(2) . ? C12 C13 1.199(2) . ? C13 C14 1.431(2) . ? C14 C20 1.394(2) . ? C14 C15 1.397(2) . ? C15 C16 1.386(2) . ? C16 C17 1.386(2) . ? C17 C19 1.388(2) . ? C17 C18 1.506(2) . ? C19 C20 1.386(2) . ? C21 C22 1.357(2) . ? C21 C29 1.491(2) . ? C22 C23 1.469(2) . ? C23 C28 1.398(2) . ? C23 C24 1.400(2) . ? C24 C25 1.391(2) . ? C25 C26 1.383(3) . ? C26 C27 1.379(3) . ? C27 C28 1.382(2) . ? C29 C30 1.389(2) . ? C29 C35 1.396(2) . ? C30 C31 1.387(2) . ? C31 C32 1.387(3) . ? C32 C34 1.389(3) . ? C32 C33 1.516(2) . ? C34 C35 1.379(2) . ? C36 C37 1.506(2) . ? C37 C38 1.392(2) . ? C37 C42 1.394(2) . ? C38 C39 1.388(2) . ? C39 C40 1.385(3) . ? C40 C41 1.379(3) . ? C41 C42 1.377(2) . ? C43 C48 1.388(2) . ? C43 C44 1.397(2) . ? C44 C45 1.382(2) . ? C45 C46 1.386(2) . ? C46 O2 1.3751(18) . ? C46 C47 1.385(2) . ? C47 C48 1.384(2) . ? C49 O2 1.442(2) . ? C49 C50 1.497(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 O1 C2 C1 107.68(16) . . ? O1 C3 C4 115.29(14) . . ? O1 C3 C8 123.96(15) . . ? C4 C3 C8 120.73(14) . . ? C5 C4 C3 120.86(14) . . ? C4 C5 C6 118.60(15) . . ? C7 C6 C5 120.49(14) . . ? C7 C6 C9 108.88(13) . . ? C5 C6 C9 130.62(14) . . ? C6 C7 C8 121.36(14) . . ? C6 C7 C11 109.94(12) . . ? C8 C7 C11 128.62(13) . . ? C7 C8 C3 117.95(14) . . ? C10 C9 C12 129.96(14) . . ? C10 C9 C6 109.64(13) . . ? C12 C9 C6 120.34(13) . . ? C9 C10 C21 127.43(14) . . ? C9 C10 C11 109.46(13) . . ? C21 C10 C11 123.09(12) . . ? C7 C11 C10 101.79(11) . . ? C7 C11 C43 105.82(11) . . ? C10 C11 C43 112.30(12) . . ? C7 C11 C36 112.67(12) . . ? C10 C11 C36 112.75(11) . . ? C43 C11 C36 111.00(11) . . ? C13 C12 C9 171.67(16) . . ? C12 C13 C14 177.45(17) . . ? C20 C14 C15 118.18(14) . . ? C20 C14 C13 120.67(14) . . ? C15 C14 C13 121.14(14) . . ? C16 C15 C14 120.35(14) . . ? C15 C16 C17 121.57(15) . . ? C16 C17 C19 117.90(15) . . ? C16 C17 C18 120.77(15) . . ? C19 C17 C18 121.33(16) . . ? C20 C19 C17 121.26(15) . . ? C19 C20 C14 120.70(15) . . ? C22 C21 C10 120.35(13) . . ? C22 C21 C29 121.15(13) . . ? C10 C21 C29 118.50(13) . . ? C21 C22 C23 128.99(14) . . ? C28 C23 C24 118.12(14) . . ? C28 C23 C22 118.57(14) . . ? C24 C23 C22 123.05(15) . . ? C25 C24 C23 119.88(16) . . ? C26 C25 C24 120.99(16) . . ? C27 C26 C25 119.54(16) . . ? C26 C27 C28 120.05(17) . . ? C27 C28 C23 121.41(16) . . ? C30 C29 C35 118.16(14) . . ? C30 C29 C21 121.50(14) . . ? C35 C29 C21 120.33(14) . . ? C31 C30 C29 120.48(17) . . ? C32 C31 C30 121.34(18) . . ? C31 C32 C34 118.01(16) . . ? C31 C32 C33 120.52(19) . . ? C34 C32 C33 121.43(19) . . ? C35 C34 C32 121.04(17) . . ? C34 C35 C29 120.98(17) . . ? C37 C36 C11 116.44(12) . . ? C38 C37 C42 117.64(15) . . ? C38 C37 C36 120.07(14) . . ? C42 C37 C36 122.14(14) . . ? C39 C38 C37 121.21(16) . . ? C40 C39 C38 119.99(16) . . ? C41 C40 C39 119.37(17) . . ? C42 C41 C40 120.49(17) . . ? C41 C42 C37 121.29(15) . . ? C48 C43 C44 116.93(14) . . ? C48 C43 C11 121.51(13) . . ? C44 C43 C11 121.31(13) . . ? C45 C44 C43 121.51(15) . . ? C44 C45 C46 120.27(15) . . ? O2 C46 C47 124.22(14) . . ? O2 C46 C45 116.48(14) . . ? C47 C46 C45 119.30(14) . . ? C48 C47 C46 119.67(15) . . ? C47 C48 C43 122.27(15) . . ? O2 C49 C50 107.56(14) . . ? C3 O1 C2 119.04(13) . . ? C46 O2 C49 116.81(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.11 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.377 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.096