# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Vijay Nair' _publ_contact_author_address ; Organic Chemistry Section National Institute for Interdisciplinary Science and technology (CSIR) Industrial Estate P.O. Pappanamcode Trivandrum Kerala 695019 INDIA ; _publ_contact_author_email 'VIJAYNAIR 2001@YAHOO.COM' _publ_section_title ; Stereoselective Synthesis of Spirocyclopentanones via N-Heterocyclic Carbene Catalyzed Reaction of Enals and Dienones ; loop_ _publ_author_name 'Vijay Nair' 'Beneesh Pattoorpadi Babu' 'E. Suresh' 'Sreekumar Vellalath' data_108bskm _database_code_depnum_ccdc_archive 'CCDC 638979' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H22 F6 O3' _chemical_formula_weight 532.47 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' F F 0.0171 0.0103 '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 8.360(3) _cell_length_b 10.923(3) _cell_length_c 14.100(4) _cell_angle_alpha 75.738(5) _cell_angle_beta 78.758(5) _cell_angle_gamma 81.972(5) _cell_volume 1218.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(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 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9522 _exptl_absorpt_correction_T_max 0.9662 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7210 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.18 _reflns_number_total 5322 _reflns_number_gt 3315 _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 ORTEP _computing_publication_material ? _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^)+(0.0871P)^2^+0.2803P] 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 5322 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1006 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1891 _refine_ls_wR_factor_gt 0.1550 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.7592(4) 0.3268(2) 0.74123(15) 0.1160(10) Uani 1 d . . . F2 F 0.7188(2) 0.52730(18) 0.69212(13) 0.0695(5) Uani 1 d . . . F3 F 0.5410(3) 0.4114(2) 0.68670(14) 0.0821(6) Uani 1 d . . . F4 F 0.9660(3) 0.9878(2) 0.31914(17) 0.0854(6) Uani 1 d . . . F5 F 0.9516(3) 1.13314(18) 0.18989(18) 0.0878(7) Uani 1 d . . . F6 F 1.1439(2) 0.9839(2) 0.1907(2) 0.1069(9) Uani 1 d . . . O1 O 0.4026(2) 0.80515(18) 0.52355(13) 0.0483(5) Uani 1 d . . . H1 H 0.3228 0.8578 0.5185 0.072 Uiso 1 calc R . . O2 O 0.2372(2) 1.01125(18) 0.46458(15) 0.0536(5) Uani 1 d . . . O3 O 0.8008(3) 1.54990(19) -0.00520(14) 0.0626(6) Uani 1 d . . . C1 C 0.7835(3) 0.4081(2) 0.5685(2) 0.0437(6) Uani 1 d . . . C2 C 0.8851(4) 0.2986(3) 0.5569(2) 0.0559(8) Uani 1 d . . . H2 H 0.9034 0.2352 0.6124 0.067 Uiso 1 calc R . . C3 C 0.9585(4) 0.2839(3) 0.4637(3) 0.0602(8) Uani 1 d . . . H3 H 1.0260 0.2106 0.4560 0.072 Uiso 1 calc R . . C4 C 0.9316(4) 0.3775(3) 0.3828(2) 0.0576(8) Uani 1 d . . . H4 H 0.9798 0.3672 0.3196 0.069 Uiso 1 calc R . . C5 C 0.8334(4) 0.4874(3) 0.3937(2) 0.0519(7) Uani 1 d . . . H5 H 0.8189 0.5509 0.3376 0.062 Uiso 1 calc R . . C6 C 0.7558(3) 0.5055(2) 0.48639(19) 0.0394(6) Uani 1 d . . . C7 C 0.6438(3) 0.6190(2) 0.49553(19) 0.0412(6) Uani 1 d . . . H7 H 0.5595 0.6105 0.5499 0.049 Uiso 1 calc R . . C8 C 0.6495(3) 0.7322(2) 0.43490(19) 0.0416(6) Uani 1 d . . . H8 H 0.7401 0.7479 0.3852 0.050 Uiso 1 calc R . . C9 C 0.5171(3) 0.8336(2) 0.44371(18) 0.0376(6) Uani 1 d . . . C10 C 0.4984(3) 0.9481(2) 0.37713(18) 0.0376(6) Uani 1 d . . . C11 C 0.3521(3) 1.0322(2) 0.3928(2) 0.0427(6) Uani 1 d . . . C12 C 0.3572(3) 1.1505(2) 0.3123(2) 0.0467(7) Uani 1 d . . . H12A H 0.3792 1.2213 0.3363 0.056 Uiso 1 calc R . . H12B H 0.2542 1.1714 0.2874 0.056 Uiso 1 calc R . . C13 C 0.4968(3) 1.1195(2) 0.23127(19) 0.0430(6) Uani 1 d . . . H13 H 0.4502 1.0810 0.1882 0.052 Uiso 1 calc R . . C14 C 0.6139(3) 1.0139(2) 0.28755(18) 0.0392(6) Uani 1 d . . . H14 H 0.6897 1.0556 0.3114 0.047 Uiso 1 calc R . . C15 C 0.5795(3) 1.2316(2) 0.16669(18) 0.0410(6) Uani 1 d . . . C16 C 0.6345(4) 1.3187(3) 0.2063(2) 0.0484(7) Uani 1 d . . . H16 H 0.6209 1.3065 0.2750 0.058 Uiso 1 calc R . . C17 C 0.7075(4) 1.4214(3) 0.1485(2) 0.0488(7) Uani 1 d . . . H17 H 0.7438 1.4776 0.1778 0.059 Uiso 1 calc R . . C18 C 0.7282(3) 1.4427(2) 0.0464(2) 0.0458(6) Uani 1 d . . . C19 C 0.6754(4) 1.3586(3) 0.0040(2) 0.0522(7) Uani 1 d . . . H19 H 0.6891 1.3716 -0.0647 0.063 Uiso 1 calc R . . C20 C 0.6018(4) 1.2546(3) 0.0640(2) 0.0493(7) Uani 1 d . . . H20 H 0.5660 1.1982 0.0347 0.059 Uiso 1 calc R . . C21 C 0.8280(5) 1.5748(3) -0.1097(2) 0.0700(10) Uani 1 d . . . H21A H 0.9040 1.5090 -0.1317 0.105 Uiso 1 calc R . . H21B H 0.8722 1.6551 -0.1363 0.105 Uiso 1 calc R . . H21C H 0.7262 1.5771 -0.1323 0.105 Uiso 1 calc R . . C22 C 0.7140(3) 0.9333(2) 0.21956(18) 0.0401(6) Uani 1 d . . . C23 C 0.6303(4) 0.8566(3) 0.1839(2) 0.0517(7) Uani 1 d . . . H23 H 0.5177 0.8553 0.2042 0.062 Uiso 1 calc R . . C24 C 0.7105(4) 0.7830(3) 0.1194(2) 0.0660(9) Uani 1 d . . . H24 H 0.6519 0.7315 0.0981 0.079 Uiso 1 calc R . . C25 C 0.8758(3) 0.7847(2) 0.08618(18) 0.0741(10) Uani 1 d . . . H25 H 0.9293 0.7351 0.0424 0.089 Uiso 1 calc R . . C26 C 0.9613(3) 0.8608(2) 0.11860(18) 0.0660(9) Uani 1 d R . . H26 H 1.0731 0.8639 0.0956 0.079 Uiso 1 calc R . . C27 C 0.8816(3) 0.9333(2) 0.1856(2) 0.0476(7) Uani 1 d . . . C28 C 0.9852(4) 1.0091(3) 0.2204(3) 0.0608(8) Uani 1 d . . . C29 C 0.7036(4) 0.4171(3) 0.6711(2) 0.0552(8) Uani 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 F1 0.188(3) 0.0845(16) 0.0541(12) 0.0022(11) -0.0369(14) 0.0496(17) F2 0.0863(14) 0.0675(12) 0.0625(11) -0.0285(9) -0.0112(10) -0.0105(10) F3 0.0867(16) 0.0950(16) 0.0641(12) -0.0223(11) 0.0143(11) -0.0371(12) F4 0.0830(15) 0.0946(16) 0.0894(16) -0.0233(12) -0.0362(12) -0.0094(11) F5 0.0812(14) 0.0498(12) 0.1339(19) -0.0107(11) -0.0270(13) -0.0175(10) F6 0.0423(12) 0.114(2) 0.171(3) -0.0568(18) -0.0027(13) -0.0058(11) O1 0.0443(11) 0.0448(11) 0.0464(11) -0.0015(8) -0.0003(9) 0.0011(8) O2 0.0443(11) 0.0496(12) 0.0568(12) -0.0086(9) 0.0055(9) 0.0040(8) O3 0.0890(17) 0.0498(12) 0.0465(12) -0.0047(9) -0.0021(11) -0.0223(11) C1 0.0501(16) 0.0344(13) 0.0473(15) -0.0076(11) -0.0136(12) -0.0009(11) C2 0.0543(18) 0.0431(16) 0.070(2) -0.0090(14) -0.0206(15) 0.0045(13) C3 0.0428(17) 0.0505(18) 0.091(2) -0.0304(17) -0.0085(16) 0.0060(13) C4 0.0526(18) 0.0583(19) 0.0606(19) -0.0227(16) 0.0040(15) -0.0030(14) C5 0.0558(18) 0.0475(17) 0.0495(16) -0.0102(13) -0.0047(14) -0.0016(13) C6 0.0385(14) 0.0333(13) 0.0465(15) -0.0071(11) -0.0093(11) -0.0042(10) C7 0.0462(15) 0.0384(14) 0.0375(13) -0.0078(11) -0.0064(11) -0.0014(11) C8 0.0380(14) 0.0401(14) 0.0455(15) -0.0079(12) -0.0057(12) -0.0044(11) C9 0.0418(14) 0.0313(12) 0.0394(13) -0.0069(10) -0.0076(11) -0.0035(10) C10 0.0420(14) 0.0314(12) 0.0390(13) -0.0093(10) -0.0058(11) -0.0010(10) C11 0.0473(16) 0.0368(14) 0.0445(15) -0.0107(12) -0.0102(13) 0.0012(11) C12 0.0430(15) 0.0367(14) 0.0556(16) -0.0066(12) -0.0064(13) 0.0027(11) C13 0.0483(16) 0.0346(14) 0.0441(15) -0.0070(11) -0.0085(12) 0.0003(11) C14 0.0426(14) 0.0305(13) 0.0435(14) -0.0076(11) -0.0067(11) -0.0021(10) C15 0.0461(15) 0.0342(13) 0.0400(14) -0.0076(11) -0.0068(11) 0.0034(11) C16 0.069(2) 0.0391(15) 0.0376(14) -0.0080(12) -0.0107(13) -0.0038(13) C17 0.0646(19) 0.0416(15) 0.0440(15) -0.0138(12) -0.0107(13) -0.0077(13) C18 0.0521(17) 0.0358(14) 0.0460(15) -0.0055(12) -0.0062(13) -0.0017(11) C19 0.071(2) 0.0517(17) 0.0323(14) -0.0087(12) -0.0074(13) -0.0036(14) C20 0.0672(19) 0.0392(15) 0.0446(15) -0.0127(12) -0.0156(14) -0.0011(13) C21 0.096(3) 0.058(2) 0.0455(18) 0.0043(15) 0.0014(17) -0.0191(18) C22 0.0477(16) 0.0279(12) 0.0402(14) -0.0011(10) -0.0073(12) 0.0004(10) C23 0.0557(18) 0.0412(15) 0.0577(17) -0.0128(13) -0.0079(14) -0.0023(12) C24 0.081(2) 0.0560(19) 0.071(2) -0.0310(17) -0.0170(18) -0.0015(16) C25 0.080(3) 0.074(2) 0.071(2) -0.040(2) 0.0004(19) 0.0073(19) C26 0.056(2) 0.065(2) 0.067(2) -0.0186(17) 0.0089(16) 0.0058(16) C27 0.0473(17) 0.0356(14) 0.0536(16) -0.0050(12) -0.0035(13) 0.0013(11) C28 0.0469(18) 0.0513(19) 0.079(2) -0.0106(16) -0.0045(16) -0.0022(13) C29 0.067(2) 0.0435(17) 0.0530(18) -0.0060(14) -0.0167(15) 0.0012(14) _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 F1 C29 1.318(3) . ? F2 C29 1.336(3) . ? F3 C29 1.342(4) . ? F4 C28 1.335(4) . ? F5 C28 1.324(4) . ? F6 C28 1.323(4) . ? O1 C9 1.330(3) . ? O1 H1 0.8200 . ? O2 C11 1.252(3) . ? O3 C18 1.370(3) . ? O3 C21 1.409(4) . ? C1 C2 1.392(4) . ? C1 C6 1.398(4) . ? C1 C29 1.490(4) . ? C2 C3 1.375(4) . ? C2 H2 0.9300 . ? C3 C4 1.364(4) . ? C3 H3 0.9300 . ? C4 C5 1.380(4) . ? C4 H4 0.9300 . ? C5 C6 1.389(4) . ? C5 H5 0.9300 . ? C6 C7 1.462(3) . ? C7 C8 1.320(4) . ? C7 H7 0.9300 . ? C8 C9 1.462(3) . ? C8 H8 0.9300 . ? C9 C10 1.377(3) . ? C10 C11 1.438(3) . ? C10 C14 1.521(3) . ? C11 C12 1.494(4) . ? C12 C13 1.531(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C15 1.499(4) . ? C13 C14 1.566(3) . ? C13 H13 0.9800 . ? C14 C22 1.514(3) . ? C14 H14 0.9800 . ? C15 C16 1.384(4) . ? C15 C20 1.387(4) . ? C16 C17 1.357(4) . ? C16 H16 0.9300 . ? C17 C18 1.380(4) . ? C17 H17 0.9300 . ? C18 C19 1.372(4) . ? C19 C20 1.379(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C27 1.389(4) . ? C22 C23 1.398(4) . ? C23 C24 1.377(4) . ? C23 H23 0.9300 . ? C24 C25 1.371(4) . ? C24 H24 0.9300 . ? C25 C26 1.3757 . ? C25 H25 0.9300 . ? C26 C27 1.392(3) . ? C26 H26 0.9300 . ? C27 C28 1.497(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 C9 O1 H1 109.5 . . ? C18 O3 C21 118.1(2) . . ? C2 C1 C6 120.9(3) . . ? C2 C1 C29 117.8(3) . . ? C6 C1 C29 121.3(2) . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 119.6(3) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.6(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 121.6(3) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 117.0(2) . . ? C5 C6 C7 120.6(2) . . ? C1 C6 C7 122.3(2) . . ? C8 C7 C6 126.9(2) . . ? C8 C7 H7 116.5 . . ? C6 C7 H7 116.5 . . ? C7 C8 C9 121.8(2) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? O1 C9 C10 119.3(2) . . ? O1 C9 C8 113.8(2) . . ? C10 C9 C8 126.8(2) . . ? C9 C10 C11 119.4(2) . . ? C9 C10 C14 131.7(2) . . ? C11 C10 C14 108.7(2) . . ? O2 C11 C10 125.2(2) . . ? O2 C11 C12 124.2(2) . . ? C10 C11 C12 110.5(2) . . ? C11 C12 C13 104.7(2) . . ? C11 C12 H12A 110.8 . . ? C13 C12 H12A 110.8 . . ? C11 C12 H12B 110.8 . . ? C13 C12 H12B 110.8 . . ? H12A C12 H12B 108.9 . . ? C15 C13 C12 115.0(2) . . ? C15 C13 C14 114.4(2) . . ? C12 C13 C14 104.8(2) . . ? C15 C13 H13 107.4 . . ? C12 C13 H13 107.4 . . ? C14 C13 H13 107.4 . . ? C22 C14 C10 117.7(2) . . ? C22 C14 C13 111.4(2) . . ? C10 C14 C13 103.0(2) . . ? C22 C14 H14 108.1 . . ? C10 C14 H14 108.1 . . ? C13 C14 H14 108.1 . . ? C16 C15 C20 116.5(2) . . ? C16 C15 C13 121.8(2) . . ? C20 C15 C13 121.7(2) . . ? C17 C16 C15 122.2(3) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C16 C17 C18 120.3(3) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? O3 C18 C19 124.9(3) . . ? O3 C18 C17 115.7(3) . . ? C19 C18 C17 119.4(3) . . ? C18 C19 C20 119.5(3) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C19 C20 C15 122.1(3) . . ? C19 C20 H20 119.0 . . ? C15 C20 H20 119.0 . . ? O3 C21 H21A 109.5 . . ? O3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C27 C22 C23 116.8(2) . . ? C27 C22 C14 125.6(2) . . ? C23 C22 C14 117.5(2) . . ? C24 C23 C22 121.6(3) . . ? C24 C23 H23 119.2 . . ? C22 C23 H23 119.2 . . ? C25 C24 C23 120.8(3) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C24 C25 C26 119.03(17) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? C25 C26 C27 120.44(17) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C22 C27 C26 121.3(3) . . ? C22 C27 C28 121.8(3) . . ? C26 C27 C28 116.9(3) . . ? F6 C28 F5 106.6(3) . . ? F6 C28 F4 105.3(3) . . ? F5 C28 F4 105.2(3) . . ? F6 C28 C27 113.0(3) . . ? F5 C28 C27 113.0(3) . . ? F4 C28 C27 113.0(3) . . ? F1 C29 F2 106.5(3) . . ? F1 C29 F3 105.7(3) . . ? F2 C29 F3 103.7(2) . . ? F1 C29 C1 113.9(3) . . ? F2 C29 C1 113.2(2) . . ? F3 C29 C1 112.9(3) . . ? _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 28.18 _diffrn_measured_fraction_theta_full 0.889 _refine_diff_density_max 0.397 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.057 # Attachment 'Compound_8a.cif' data_iiipbb1m _database_code_depnum_ccdc_archive 'CCDC 653444' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 O4' _chemical_formula_weight 452.52 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' O O 0.0106 0.0060 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 43.220(18) _cell_length_b 6.205(3) _cell_length_c 17.784(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.239(10) _cell_angle_gamma 90.00 _cell_volume 4741(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour colurless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9620 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11325 _diffrn_reflns_av_R_equivalents 0.1007 _diffrn_reflns_av_sigmaI/netI 0.1266 _diffrn_reflns_limit_h_min -50 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4166 _reflns_number_gt 2262 _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 ORTEP _computing_publication_material ? _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^)+(0.0726P)^2^+1.7574P] 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 SHELXL _refine_ls_extinction_coef 0.0014(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4166 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1775 _refine_ls_R_factor_gt 0.0966 _refine_ls_wR_factor_ref 0.2157 _refine_ls_wR_factor_gt 0.1833 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 O1 O 0.14907(7) 0.6153(5) 0.49500(18) 0.0506(10) Uani 1 1 d . . . O2 O 0.18748(7) 0.0748(6) 0.5104(2) 0.0605(11) Uani 1 1 d . . . O3 O 0.24218(7) 0.6471(6) 0.10088(18) 0.0514(10) Uani 1 1 d . . . O4 O -0.01020(7) 0.3721(6) 0.3825(2) 0.0626(11) Uani 1 1 d . . . C1 C 0.21030(9) 0.7693(7) 0.2739(3) 0.0361(12) Uani 1 1 d . . . H1 H 0.2118 0.8804 0.3092 0.043 Uiso 1 1 calc R . . C2 C 0.22623(9) 0.7856(8) 0.2114(3) 0.0418(13) Uani 1 1 d . . . H2 H 0.2383 0.9071 0.2049 0.050 Uiso 1 1 calc R . . C3 C 0.22448(10) 0.6219(8) 0.1579(3) 0.0385(12) Uani 1 1 d . . . C4 C 0.20563(10) 0.4466(8) 0.1683(3) 0.0475(14) Uani 1 1 d . . . H4 H 0.2037 0.3373 0.1323 0.057 Uiso 1 1 calc R . . C5 C 0.18983(11) 0.4314(8) 0.2304(3) 0.0471(14) Uani 1 1 d . . . H5 H 0.1773 0.3116 0.2357 0.056 Uiso 1 1 calc R . . C6 C 0.19191(10) 0.5896(7) 0.2858(3) 0.0361(12) Uani 1 1 d . . . C7 C 0.17680(9) 0.5796(8) 0.3552(2) 0.0370(12) Uani 1 1 d . . . H7 H 0.1795 0.7019 0.3854 0.044 Uiso 1 1 calc R . . C8 C 0.15971(9) 0.4249(7) 0.3827(2) 0.0344(12) Uani 1 1 d . . . C9 C 0.15048(10) 0.2063(7) 0.3529(3) 0.0407(13) Uani 1 1 d . . . H9A H 0.1686 0.1138 0.3530 0.049 Uiso 1 1 calc R . . H9B H 0.1403 0.2161 0.3016 0.049 Uiso 1 1 calc R . . C10 C 0.12773(10) 0.1165(7) 0.4069(2) 0.0372(12) Uani 1 1 d . . . H10A H 0.1063 0.1446 0.3870 0.045 Uiso 1 1 calc R . . H10B H 0.1305 -0.0377 0.4136 0.045 Uiso 1 1 calc R . . C11 C 0.13591(9) 0.2349(7) 0.4818(2) 0.0305(11) Uani 1 1 d . . . C12 C 0.14872(9) 0.4504(8) 0.4574(3) 0.0356(12) Uani 1 1 d . . . C13 C 0.16230(10) 0.1130(7) 0.5302(3) 0.0380(12) Uani 1 1 d . . . C14 C 0.15092(9) 0.0454(8) 0.6029(3) 0.0423(13) Uani 1 1 d . . . H14A H 0.1590 0.1403 0.6438 0.051 Uiso 1 1 calc R . . H14B H 0.1574 -0.1010 0.6157 0.051 Uiso 1 1 calc R . . C15 C 0.11573(9) 0.0603(7) 0.5895(2) 0.0346(12) Uani 1 1 d . . . H15 H 0.1080 -0.0692 0.5620 0.042 Uiso 1 1 calc R . . C16 C 0.11036(9) 0.2537(7) 0.5355(2) 0.0326(11) Uani 1 1 d . . . H16 H 0.1153 0.3826 0.5663 0.039 Uiso 1 1 calc R . . C17 C 0.09911(10) 0.0788(9) 0.6602(3) 0.0428(13) Uani 1 1 d . . . C18 C 0.10578(11) 0.2453(10) 0.7115(3) 0.0553(15) Uani 1 1 d . . . H18 H 0.1211 0.3452 0.7034 0.066 Uiso 1 1 calc R . . C19 C 0.08996(13) 0.2637(11) 0.7739(3) 0.0688(18) Uani 1 1 d . . . H19 H 0.0945 0.3762 0.8079 0.083 Uiso 1 1 calc R . . C20 C 0.06760(14) 0.1165(13) 0.7861(3) 0.073(2) Uani 1 1 d . . . H20 H 0.0570 0.1290 0.8286 0.088 Uiso 1 1 calc R . . C21 C 0.06054(14) -0.0495(13) 0.7365(4) 0.084(2) Uani 1 1 d . . . H21 H 0.0452 -0.1487 0.7450 0.101 Uiso 1 1 calc R . . C22 C 0.07645(12) -0.0677(9) 0.6740(3) 0.0590(16) Uani 1 1 d . . . H22 H 0.0718 -0.1810 0.6404 0.071 Uiso 1 1 calc R . . C23 C 0.07789(9) 0.2858(7) 0.4979(2) 0.0281(11) Uani 1 1 d . . . C24 C 0.05715(10) 0.1174(8) 0.4803(3) 0.0462(14) Uani 1 1 d . . . H24 H 0.0630 -0.0225 0.4941 0.055 Uiso 1 1 calc R . . C25 C 0.02818(10) 0.1543(8) 0.4431(3) 0.0483(14) Uani 1 1 d . . . H25 H 0.0146 0.0388 0.4330 0.058 Uiso 1 1 calc R . . C26 C 0.01879(10) 0.3539(8) 0.4205(3) 0.0399(13) Uani 1 1 d . . . C27 C 0.03837(11) 0.5243(9) 0.4382(3) 0.0540(15) Uani 1 1 d . . . H27 H 0.0321 0.6636 0.4247 0.065 Uiso 1 1 calc R . . C28 C 0.06756(10) 0.4881(8) 0.4765(3) 0.0479(14) Uani 1 1 d . . . H28 H 0.0807 0.6052 0.4880 0.058 Uiso 1 1 calc R . . C29 C 0.24033(12) 0.4898(9) 0.0428(3) 0.0598(16) Uani 1 1 d . . . H29A H 0.2473 0.3533 0.0637 0.090 Uiso 1 1 calc R . . H29B H 0.2533 0.5321 0.0048 0.090 Uiso 1 1 calc R . . H29C H 0.2192 0.4774 0.0204 0.090 Uiso 1 1 calc R . . C30 C -0.02068(12) 0.5808(10) 0.3574(3) 0.078(2) Uani 1 1 d . . . H30A H -0.0227 0.6710 0.4004 0.117 Uiso 1 1 calc R . . H30B H -0.0405 0.5683 0.3276 0.117 Uiso 1 1 calc R . . H30C H -0.0059 0.6433 0.3273 0.117 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.076(2) 0.036(2) 0.044(2) -0.0095(17) 0.0236(18) -0.0169(18) O2 0.0338(19) 0.072(3) 0.078(3) 0.009(2) 0.0181(19) 0.0098(18) O3 0.054(2) 0.057(3) 0.048(2) 0.0006(19) 0.0252(18) -0.0075(18) O4 0.041(2) 0.061(3) 0.080(3) 0.005(2) -0.0188(19) 0.0085(19) C1 0.034(3) 0.036(3) 0.039(3) 0.001(2) 0.006(2) -0.003(2) C2 0.034(3) 0.041(3) 0.051(3) 0.007(3) 0.007(2) -0.007(2) C3 0.032(3) 0.043(3) 0.041(3) -0.001(3) 0.006(2) 0.000(2) C4 0.053(3) 0.048(4) 0.043(3) -0.010(3) 0.012(3) -0.019(3) C5 0.053(3) 0.042(3) 0.049(3) -0.010(3) 0.019(3) -0.018(3) C6 0.031(3) 0.032(3) 0.044(3) 0.001(2) 0.003(2) -0.006(2) C7 0.035(3) 0.036(3) 0.040(3) -0.003(2) 0.007(2) 0.000(2) C8 0.032(2) 0.036(3) 0.037(3) -0.006(2) 0.011(2) -0.008(2) C9 0.045(3) 0.032(3) 0.047(3) -0.011(2) 0.012(2) -0.012(2) C10 0.032(2) 0.030(3) 0.050(3) -0.003(2) 0.009(2) -0.009(2) C11 0.027(2) 0.029(3) 0.035(3) -0.003(2) -0.002(2) -0.004(2) C12 0.031(3) 0.034(3) 0.043(3) -0.003(2) 0.009(2) -0.007(2) C13 0.036(3) 0.026(3) 0.054(3) -0.004(2) 0.009(2) 0.000(2) C14 0.037(3) 0.042(3) 0.048(3) 0.003(3) 0.003(2) 0.008(2) C15 0.032(3) 0.033(3) 0.038(3) -0.002(2) 0.000(2) 0.001(2) C16 0.030(2) 0.034(3) 0.034(3) -0.002(2) 0.003(2) 0.005(2) C17 0.033(3) 0.057(4) 0.037(3) 0.015(3) -0.004(2) 0.003(3) C18 0.050(3) 0.069(4) 0.045(3) -0.011(3) 0.002(3) 0.003(3) C19 0.069(4) 0.102(6) 0.035(3) -0.010(3) 0.001(3) 0.024(4) C20 0.064(4) 0.118(7) 0.041(4) 0.023(4) 0.017(3) 0.026(4) C21 0.068(4) 0.128(7) 0.058(4) 0.019(4) 0.013(4) -0.022(4) C22 0.064(4) 0.065(4) 0.051(4) 0.010(3) 0.022(3) -0.007(3) C23 0.026(2) 0.030(3) 0.028(2) 0.000(2) 0.0057(19) 0.001(2) C24 0.044(3) 0.022(3) 0.071(4) -0.004(3) -0.002(3) 0.002(2) C25 0.032(3) 0.036(4) 0.074(4) -0.003(3) -0.004(3) -0.006(2) C26 0.023(2) 0.045(4) 0.050(3) -0.001(3) -0.003(2) 0.008(2) C27 0.042(3) 0.036(3) 0.082(4) 0.011(3) -0.002(3) 0.008(3) C28 0.036(3) 0.035(3) 0.071(4) 0.002(3) -0.005(3) -0.003(2) C29 0.061(4) 0.073(4) 0.049(3) -0.008(3) 0.023(3) -0.003(3) C30 0.058(4) 0.089(5) 0.085(5) 0.033(4) -0.006(3) 0.016(4) _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 C12 1.222(5) . ? O2 C13 1.203(5) . ? O3 C3 1.344(5) . ? O3 C29 1.418(6) . ? O4 C26 1.362(5) . ? O4 C30 1.427(6) . ? C1 C2 1.373(6) . ? C1 C6 1.398(6) . ? C2 C3 1.389(6) . ? C3 C4 1.384(6) . ? C4 C5 1.364(6) . ? C5 C6 1.388(6) . ? C6 C7 1.458(6) . ? C7 C8 1.336(6) . ? C8 C12 1.467(6) . ? C8 C9 1.495(6) . ? C9 C10 1.551(5) . ? C10 C11 1.529(6) . ? C11 C12 1.529(6) . ? C11 C16 1.541(5) . ? C11 C13 1.549(6) . ? C13 C14 1.493(6) . ? C14 C15 1.517(5) . ? C15 C17 1.519(6) . ? C15 C16 1.538(6) . ? C16 C23 1.501(5) . ? C17 C22 1.378(6) . ? C17 C18 1.387(7) . ? C18 C19 1.371(7) . ? C19 C20 1.364(8) . ? C20 C21 1.369(8) . ? C21 C22 1.374(7) . ? C23 C28 1.373(6) . ? C23 C24 1.390(6) . ? C24 C25 1.371(6) . ? C25 C26 1.351(6) . ? C26 C27 1.369(6) . ? C27 C28 1.385(6) . ? 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 C3 O3 C29 118.6(4) . . ? C26 O4 C30 118.3(4) . . ? C2 C1 C6 121.6(5) . . ? C1 C2 C3 120.4(4) . . ? O3 C3 C4 125.7(4) . . ? O3 C3 C2 116.0(4) . . ? C4 C3 C2 118.2(4) . . ? C5 C4 C3 121.1(5) . . ? C4 C5 C6 121.8(5) . . ? C5 C6 C1 116.8(4) . . ? C5 C6 C7 124.8(4) . . ? C1 C6 C7 118.4(4) . . ? C8 C7 C6 131.0(4) . . ? C7 C8 C12 120.0(4) . . ? C7 C8 C9 131.2(4) . . ? C12 C8 C9 108.6(4) . . ? C8 C9 C10 105.6(4) . . ? C11 C10 C9 105.4(3) . . ? C12 C11 C10 103.2(3) . . ? C12 C11 C16 114.6(4) . . ? C10 C11 C16 117.6(3) . . ? C12 C11 C13 108.5(3) . . ? C10 C11 C13 109.6(4) . . ? C16 C11 C13 103.1(3) . . ? O1 C12 C8 126.9(4) . . ? O1 C12 C11 124.1(4) . . ? C8 C12 C11 109.0(4) . . ? O2 C13 C14 126.3(4) . . ? O2 C13 C11 124.6(4) . . ? C14 C13 C11 109.0(4) . . ? C13 C14 C15 105.4(4) . . ? C14 C15 C17 115.5(4) . . ? C14 C15 C16 103.1(3) . . ? C17 C15 C16 113.9(4) . . ? C23 C16 C15 116.9(4) . . ? C23 C16 C11 115.6(3) . . ? C15 C16 C11 104.9(3) . . ? C22 C17 C18 118.4(5) . . ? C22 C17 C15 120.5(5) . . ? C18 C17 C15 121.2(5) . . ? C19 C18 C17 120.6(6) . . ? C20 C19 C18 119.8(6) . . ? C19 C20 C21 121.0(6) . . ? C20 C21 C22 119.1(6) . . ? C21 C22 C17 121.2(6) . . ? C28 C23 C24 116.3(4) . . ? C28 C23 C16 120.3(4) . . ? C24 C23 C16 123.3(4) . . ? C25 C24 C23 121.1(4) . . ? C26 C25 C24 121.7(5) . . ? C25 C26 O4 117.0(4) . . ? C25 C26 C27 118.8(4) . . ? O4 C26 C27 124.2(5) . . ? C26 C27 C28 119.7(5) . . ? C23 C28 C27 122.4(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.239 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.055