# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_110117a_0m _database_code_depnum_ccdc_archive 'CCDC 918901' #TrackingRef '1CA.cif' _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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 19.586(2) _cell_length_b 5.6198(7) _cell_length_c 13.7767(16) _cell_angle_alpha 90.00 _cell_angle_beta 125.672(2) _cell_angle_gamma 90.00 _cell_volume 1231.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1314 _cell_measurement_theta_min 3.64 _cell_measurement_theta_max 24.07 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_T_max 0.9842 _exptl_absorpt_process_details 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 '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 3285 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1327 _reflns_number_gt 1125 _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^)+(0.0518P)^2^+0.0977P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(2) _refine_ls_number_reflns 1327 _refine_ls_number_parameters 156 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 1.1623(2) -0.1126(7) 0.5857(2) 0.0966(11) Uani 1 1 d . . . H1A H 1.1683 -0.2541 0.5523 0.145 Uiso 1 1 calc R . . H1B H 1.1082 -0.1125 0.5718 0.145 Uiso 1 1 calc R . . H1C H 1.2056 -0.1084 0.6701 0.145 Uiso 1 1 calc R . . C2 C 1.11929(13) 0.0975(5) 0.40796(17) 0.0545(5) Uani 1 1 d . . . C3 C 1.05772(14) -0.0674(5) 0.33611(19) 0.0595(6) Uani 1 1 d . . . H3 H 1.0473 -0.1923 0.3701 0.071 Uiso 1 1 calc R . . C4 C 1.01151(14) -0.0459(5) 0.21302(19) 0.0557(6) Uani 1 1 d . . . H4 H 0.9692 -0.1556 0.1650 0.067 Uiso 1 1 calc R . . C5 C 1.02684(12) 0.1348(4) 0.15963(17) 0.0479(5) Uani 1 1 d . . . C6 C 1.08730(13) 0.3020(5) 0.23394(19) 0.0556(6) Uani 1 1 d . . . H6 H 1.0976 0.4286 0.2006 0.067 Uiso 1 1 calc R . . C7 C 1.13269(14) 0.2836(5) 0.35689(19) 0.0579(6) Uani 1 1 d . . . H7 H 1.1726 0.3985 0.4052 0.069 Uiso 1 1 calc R . . C8 C 0.98012(12) 0.1377(4) 0.02664(17) 0.0510(5) Uani 1 1 d . . . C9 C 0.88661(12) 0.1185(4) -0.04189(17) 0.0474(5) Uani 1 1 d . . . C10 C 0.84114(13) 0.2803(5) -0.02473(17) 0.0519(5) Uani 1 1 d . . . H10 H 0.8695 0.4018 0.0308 0.062 Uiso 1 1 calc R . . C11 C 0.75482(13) 0.2654(5) -0.08800(18) 0.0531(5) Uani 1 1 d . . . H11 H 0.7256 0.3787 -0.0764 0.064 Uiso 1 1 calc R . . C12 C 0.71195(12) 0.0829(4) -0.16828(17) 0.0486(5) Uani 1 1 d . . . C13 C 0.58179(15) -0.1125(7) -0.3047(3) 0.0875(9) Uani 1 1 d . . . H13A H 0.6043 -0.2588 -0.2611 0.131 Uiso 1 1 calc R . . H13B H 0.5873 -0.1103 -0.3695 0.131 Uiso 1 1 calc R . . H13C H 0.5235 -0.1003 -0.3358 0.131 Uiso 1 1 calc R . . C14 C 0.75561(13) -0.0839(5) -0.1853(2) 0.0590(6) Uani 1 1 d . . . H14 H 0.7273 -0.2083 -0.2390 0.071 Uiso 1 1 calc R . . C15 C 0.84209(14) -0.0644(5) -0.1217(2) 0.0587(6) Uani 1 1 d . . . H15 H 0.8712 -0.1785 -0.1331 0.070 Uiso 1 1 calc R . . O1 O 1.16948(12) 0.0900(4) 0.53104(13) 0.0773(5) Uani 1 1 d . . . O2 O 0.62640(9) 0.0816(4) -0.22761(14) 0.0668(5) 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 0.137(3) 0.082(2) 0.0588(15) 0.0137(17) 0.0505(18) 0.008(2) C2 0.0583(12) 0.0558(14) 0.0455(11) 0.0016(12) 0.0280(10) 0.0075(12) C3 0.0678(15) 0.0547(14) 0.0565(13) 0.0065(12) 0.0366(12) -0.0021(13) C4 0.0540(13) 0.0540(14) 0.0551(12) -0.0056(12) 0.0295(11) -0.0103(11) C5 0.0441(11) 0.0518(13) 0.0467(10) -0.0011(10) 0.0258(9) -0.0014(10) C6 0.0629(13) 0.0503(14) 0.0563(12) 0.0005(12) 0.0363(11) -0.0054(11) C7 0.0586(13) 0.0542(14) 0.0522(12) -0.0079(12) 0.0275(11) -0.0053(12) C8 0.0483(12) 0.0528(14) 0.0479(11) -0.0041(11) 0.0259(9) -0.0022(10) C9 0.0506(11) 0.0479(12) 0.0442(10) 0.0019(11) 0.0278(9) -0.0007(11) C10 0.0573(12) 0.0540(14) 0.0407(10) -0.0048(10) 0.0263(10) 0.0011(11) C11 0.0575(12) 0.0556(14) 0.0486(11) 0.0017(12) 0.0323(10) 0.0107(12) C12 0.0467(10) 0.0543(14) 0.0446(10) 0.0090(11) 0.0264(9) 0.0038(11) C13 0.0499(14) 0.094(2) 0.100(2) -0.013(2) 0.0339(15) -0.0171(16) C14 0.0548(13) 0.0508(14) 0.0665(14) -0.0149(13) 0.0325(11) -0.0110(11) C15 0.0547(13) 0.0499(14) 0.0747(14) -0.0128(13) 0.0396(12) -0.0007(11) O1 0.0901(12) 0.0768(13) 0.0460(8) 0.0037(10) 0.0289(9) 0.0018(11) O2 0.0461(8) 0.0770(13) 0.0704(10) 0.0002(10) 0.0300(8) 0.0035(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.416(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C7 1.368(3) . ? C2 O1 1.378(2) . ? C2 C3 1.379(3) . ? C3 C4 1.385(3) . ? C3 H3 0.9300 . ? C4 C5 1.386(3) . ? C4 H4 0.9300 . ? C5 C6 1.385(3) . ? C5 C8 1.496(3) . ? C6 C7 1.383(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C8 1.346(4) 2_755 ? C8 C9 1.497(3) . ? C9 C15 1.381(3) . ? C9 C10 1.386(3) . ? C10 C11 1.381(3) . ? C10 H10 0.9300 . ? C11 C12 1.377(3) . ? C11 H11 0.9300 . ? C12 O2 1.370(2) . ? C12 C14 1.378(3) . ? C13 O2 1.414(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.385(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 O1 116.3(2) . . ? C7 C2 C3 119.62(19) . . ? O1 C2 C3 124.1(2) . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 121.6(2) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C6 C5 C4 117.47(18) . . ? C6 C5 C8 123.1(2) . . ? C4 C5 C8 119.4(2) . . ? C7 C6 C5 121.1(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C2 C7 C6 120.5(2) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C8 C8 C5 122.2(2) 2_755 . ? C8 C8 C9 122.7(2) 2_755 . ? C5 C8 C9 114.90(16) . . ? C15 C9 C10 116.99(18) . . ? C15 C9 C8 121.9(2) . . ? C10 C9 C8 121.1(2) . . ? C11 C10 C9 121.6(2) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C12 C11 C10 120.0(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? O2 C12 C11 116.34(19) . . ? O2 C12 C14 124.0(2) . . ? C11 C12 C14 119.67(18) . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 C15 119.3(2) . . ? C12 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C9 C15 C14 122.3(2) . . ? C9 C15 H15 118.9 . . ? C14 C15 H15 118.9 . . ? C2 O1 C1 117.3(2) . . ? C12 O2 C13 117.2(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.111 _refine_diff_density_min -0.108 _refine_diff_density_rms 0.025