# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 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_stu7094 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 O2' _chemical_formula_weight 226.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 25.2302(7) _cell_length_b 25.2302(7) _cell_length_c 10.3026(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5679.6(4) _cell_formula_units_Z 18 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2154 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2160 _exptl_absorpt_coefficient_mu 0.623 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6987 _exptl_absorpt_correction_T_max 0.9403 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16174 _diffrn_reflns_av_R_equivalents 0.054 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.75 _diffrn_reflns_theta_max 66.83 _reflns_number_total 2209 _reflns_number_gt 1829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogen at O2 atom was refined freely. ; _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^)+(0.0418P)^2^+3.9846P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2209 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.84127(5) 0.74622(5) 0.13354(11) 0.0556(3) Uani 1 1 d . . . O2 O 0.91317(5) 0.88550(5) 0.03085(12) 0.0635(3) Uani 1 1 d . . . H02 H 0.9033(9) 0.9121(10) -0.0003(19) 0.080(6) Uiso 1 1 d . . . C1 C 0.81971(7) 0.78800(6) 0.09515(14) 0.0461(4) Uani 1 1 d . . . C2 C 0.87220(7) 0.85272(7) 0.13449(15) 0.0506(4) Uani 1 1 d . . . H2 H 0.8555 0.8769 0.1728 0.061 Uiso 1 1 calc R . . C3 C 0.90476(7) 0.83667(8) 0.23519(15) 0.0556(4) Uani 1 1 d . . . C4 C 0.88467(7) 0.77526(8) 0.22713(15) 0.0538(4) Uani 1 1 d . . . C5 C 0.90719(9) 0.74602(10) 0.30462(18) 0.0722(5) Uani 1 1 d . . . H5 H 0.8928 0.7043 0.2975 0.087 Uiso 1 1 calc R . . C6 C 0.95170(11) 0.78181(15) 0.3921(2) 0.0922(7) Uani 1 1 d . . . H6 H 0.9674 0.7637 0.4470 0.111 Uiso 1 1 calc R . . C7 C 0.97376(10) 0.84335(15) 0.4010(2) 0.0976(8) Uani 1 1 d . . . H7 H 1.0046 0.8664 0.4604 0.117 Uiso 1 1 calc R . . C8 C 0.95053(9) 0.87225(11) 0.3219(2) 0.0810(6) Uani 1 1 d . . . H8 H 0.9655 0.9142 0.3278 0.097 Uiso 1 1 calc R . . C9 C 0.80680(8) 0.77865(9) -0.04926(15) 0.0635(5) Uani 1 1 d . . . H9A H 0.8436 0.7877 -0.0946 0.095 Uiso 1 1 calc R . . H9B H 0.7925 0.8054 -0.0793 0.095 Uiso 1 1 calc R . . H9C H 0.7760 0.7369 -0.0654 0.095 Uiso 1 1 calc R . . C10 C 0.76213(6) 0.77207(6) 0.17225(13) 0.0429(3) Uani 1 1 d . . . C11 C 0.72978(7) 0.80192(7) 0.14443(15) 0.0497(4) Uani 1 1 d . . . H11 H 0.7437 0.8314 0.0794 0.060 Uiso 1 1 calc R . . C12 C 0.67717(7) 0.78840(8) 0.21189(16) 0.0563(4) Uani 1 1 d . . . H12 H 0.6559 0.8086 0.1919 0.068 Uiso 1 1 calc R . . C13 C 0.65616(7) 0.74484(8) 0.30887(16) 0.0595(4) Uani 1 1 d . . . H13 H 0.6208 0.7357 0.3545 0.071 Uiso 1 1 calc R . . C14 C 0.68769(8) 0.71509(8) 0.33755(16) 0.0597(4) Uani 1 1 d . . . H14 H 0.6736 0.6857 0.4029 0.072 Uiso 1 1 calc R . . C15 C 0.74035(7) 0.72843(7) 0.27001(14) 0.0516(4) Uani 1 1 d . . . H15 H 0.7613 0.7079 0.2904 0.062 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 0.0650(7) 0.0549(6) 0.0605(7) 0.0026(5) 0.0002(5) 0.0401(6) O2 0.0539(7) 0.0619(7) 0.0833(8) 0.0265(6) 0.0199(6) 0.0354(6) C1 0.0522(8) 0.0469(8) 0.0474(8) 0.0035(6) 0.0001(6) 0.0310(7) C2 0.0460(8) 0.0503(8) 0.0590(9) 0.0048(7) 0.0094(7) 0.0268(7) C3 0.0462(8) 0.0685(10) 0.0528(9) 0.0009(7) 0.0029(7) 0.0293(8) C4 0.0540(9) 0.0688(11) 0.0498(9) 0.0100(7) 0.0079(7) 0.0391(8) C5 0.0695(11) 0.1005(14) 0.0674(11) 0.0269(10) 0.0150(9) 0.0582(11) C6 0.0764(14) 0.150(2) 0.0691(14) 0.0276(14) 0.0063(11) 0.0712(16) C7 0.0690(13) 0.152(2) 0.0694(13) -0.0075(14) -0.0187(10) 0.0531(16) C8 0.0623(11) 0.0957(15) 0.0775(13) -0.0135(11) -0.0078(10) 0.0337(11) C9 0.0732(11) 0.0784(12) 0.0477(9) -0.0001(8) 0.0021(8) 0.0446(10) C10 0.0455(8) 0.0421(7) 0.0409(8) -0.0022(6) -0.0042(6) 0.0218(6) C11 0.0531(9) 0.0485(8) 0.0499(8) 0.0030(6) 0.0011(7) 0.0273(7) C12 0.0540(9) 0.0626(10) 0.0584(10) -0.0062(8) -0.0030(7) 0.0337(8) C13 0.0484(9) 0.0664(10) 0.0540(10) -0.0059(8) 0.0033(7) 0.0215(8) C14 0.0595(10) 0.0586(10) 0.0470(9) 0.0069(7) 0.0043(7) 0.0190(8) C15 0.0553(9) 0.0508(8) 0.0473(8) 0.0053(7) -0.0040(7) 0.0256(7) _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 C4 1.3650(19) . ? O1 C1 1.4618(16) . ? O2 C2 1.4275(18) . ? O2 H02 0.88(2) . ? C1 C9 1.516(2) . ? C1 C10 1.523(2) . ? C1 C2 1.556(2) . ? C2 C3 1.499(2) . ? C2 H2 0.9800 . ? C3 C4 1.371(2) . ? C3 C8 1.379(3) . ? C4 C5 1.387(2) . ? C5 C6 1.369(3) . ? C5 H5 0.9300 . ? C6 C7 1.366(4) . ? C6 H6 0.9300 . ? C7 C8 1.402(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.387(2) . ? C10 C11 1.390(2) . ? C11 C12 1.381(2) . ? C11 H11 0.9300 . ? C12 C13 1.380(2) . ? C12 H12 0.9300 . ? C13 C14 1.371(2) . ? C13 H13 0.9300 . ? C14 C15 1.384(2) . ? 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 C4 O1 C1 106.98(11) . . ? C2 O2 H02 108.3(13) . . ? O1 C1 C9 106.36(12) . . ? O1 C1 C10 108.56(11) . . ? C9 C1 C10 111.62(12) . . ? O1 C1 C2 104.94(11) . . ? C9 C1 C2 115.01(13) . . ? C10 C1 C2 109.88(11) . . ? O2 C2 C3 109.78(12) . . ? O2 C2 C1 113.76(12) . . ? C3 C2 C1 100.98(12) . . ? O2 C2 H2 110.6 . . ? C3 C2 H2 110.6 . . ? C1 C2 H2 110.6 . . ? C4 C3 C8 119.41(17) . . ? C4 C3 C2 108.70(14) . . ? C8 C3 C2 131.78(17) . . ? O1 C4 C3 113.16(13) . . ? O1 C4 C5 123.59(16) . . ? C3 C4 C5 123.24(17) . . ? C6 C5 C4 116.6(2) . . ? C6 C5 H5 121.7 . . ? C4 C5 H5 121.7 . . ? C7 C6 C5 121.8(2) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C8 120.9(2) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C3 C8 C7 118.0(2) . . ? C3 C8 H8 121.0 . . ? C7 C8 H8 121.0 . . ? C1 C9 H9A 109.5 . . ? C1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 118.23(14) . . ? C15 C10 C1 122.38(13) . . ? C11 C10 C1 119.39(12) . . ? C12 C11 C10 120.97(14) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C13 C12 C11 120.01(15) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 119.66(15) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 120.50(15) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 120.62(15) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 O1 C1 C9 144.46(13) . . . . ? C4 O1 C1 C10 -95.29(13) . . . . ? C4 O1 C1 C2 22.16(14) . . . . ? O1 C1 C2 O2 96.08(13) . . . . ? C9 C1 C2 O2 -20.43(18) . . . . ? C10 C1 C2 O2 -147.38(12) . . . . ? O1 C1 C2 C3 -21.45(14) . . . . ? C9 C1 C2 C3 -137.95(13) . . . . ? C10 C1 C2 C3 95.10(13) . . . . ? O2 C2 C3 C4 -106.45(14) . . . . ? C1 C2 C3 C4 13.94(15) . . . . ? O2 C2 C3 C8 69.5(2) . . . . ? C1 C2 C3 C8 -170.13(18) . . . . ? C1 O1 C4 C3 -14.06(17) . . . . ? C1 O1 C4 C5 167.18(14) . . . . ? C8 C3 C4 O1 -177.27(15) . . . . ? C2 C3 C4 O1 -0.75(18) . . . . ? C8 C3 C4 C5 1.5(2) . . . . ? C2 C3 C4 C5 178.02(14) . . . . ? O1 C4 C5 C6 178.51(16) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C4 C5 C6 C7 -1.3(3) . . . . ? C5 C6 C7 C8 1.3(4) . . . . ? C4 C3 C8 C7 -1.4(3) . . . . ? C2 C3 C8 C7 -177.02(18) . . . . ? C6 C7 C8 C3 0.1(3) . . . . ? O1 C1 C10 C15 5.66(18) . . . . ? C9 C1 C10 C15 122.58(15) . . . . ? C2 C1 C10 C15 -108.59(15) . . . . ? O1 C1 C10 C11 -174.22(12) . . . . ? C9 C1 C10 C11 -57.30(18) . . . . ? C2 C1 C10 C11 71.53(16) . . . . ? C15 C10 C11 C12 -0.3(2) . . . . ? C1 C10 C11 C12 179.63(13) . . . . ? C10 C11 C12 C13 0.3(2) . . . . ? C11 C12 C13 C14 -0.1(2) . . . . ? C12 C13 C14 C15 0.0(2) . . . . ? C13 C14 C15 C10 0.0(2) . . . . ? C11 C10 C15 C14 0.1(2) . . . . ? C1 C10 C15 C14 -179.75(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H02 O2 0.88(2) 1.82(2) 2.6870(12) 168.4(19) 11_565 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 66.83 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.118 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.029 _database_code_depnum_ccdc_archive 'CCDC 963177' ####################################################################### # # 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_stu7111 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 O3' _chemical_formula_weight 310.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 12.99680(10) _cell_length_b 13.43520(10) _cell_length_c 10.00760(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.3940(10) _cell_angle_gamma 90.00 _cell_volume 1713.03(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2920 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.636 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8321 _exptl_absorpt_correction_T_max 0.9391 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13135 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.78 _diffrn_reflns_theta_max 67.21 _reflns_number_total 2981 _reflns_number_gt 2678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0603P)^2^+0.4560P] 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 2981 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.34645(7) 0.54182(8) 0.53045(10) 0.0462(3) Uani 1 1 d . . . O2 O 0.12983(8) 0.66319(8) 0.42937(10) 0.0460(3) Uani 1 1 d . . . O3 O 0.01127(9) 0.65864(10) 0.56568(12) 0.0625(3) Uani 1 1 d . . . C1 C 0.25101(10) 0.54876(11) 0.58788(14) 0.0415(3) Uani 1 1 d . . . C2 C 0.15982(11) 0.56025(11) 0.46171(14) 0.0430(3) Uani 1 1 d . . . H2 H 0.0985 0.5191 0.4710 0.052 Uiso 1 1 calc R . . C3 C 0.20948(11) 0.52407(11) 0.34818(14) 0.0432(3) Uani 1 1 d . . . C4 C 0.31676(11) 0.51889(11) 0.39543(14) 0.0431(3) Uani 1 1 d . . . C5 C 0.38611(13) 0.49549(12) 0.31125(16) 0.0520(4) Uani 1 1 d . . . H5 H 0.4589 0.4917 0.3448 0.062 Uiso 1 1 calc R . . C6 C 0.34320(15) 0.47796(13) 0.17582(17) 0.0587(4) Uani 1 1 d . . . H6 H 0.3879 0.4627 0.1154 0.070 Uiso 1 1 calc R . . C7 C 0.23580(15) 0.48230(14) 0.12657(17) 0.0618(5) Uani 1 1 d . . . H7 H 0.2089 0.4693 0.0340 0.074 Uiso 1 1 calc R . . C8 C 0.16788(13) 0.50560(12) 0.21249(16) 0.0530(4) Uani 1 1 d . . . H8 H 0.0951 0.5088 0.1792 0.064 Uiso 1 1 calc R . . C9 C 0.05302(12) 0.70249(13) 0.48602(16) 0.0501(4) Uani 1 1 d . . . C10 C 0.03030(15) 0.80653(14) 0.43691(19) 0.0646(5) Uani 1 1 d . . . H10A H -0.0388 0.8259 0.4505 0.097 Uiso 1 1 calc R . . H10B H 0.0323 0.8103 0.3407 0.097 Uiso 1 1 calc R . . H10C H 0.0826 0.8511 0.4876 0.097 Uiso 1 1 calc R . . C11 C 0.23620(12) 0.45169(11) 0.65981(15) 0.0471(4) Uani 1 1 d . . . C12 C 0.14779(15) 0.44068(14) 0.71829(16) 0.0590(4) Uani 1 1 d . . . H12 H 0.0986 0.4926 0.7114 0.071 Uiso 1 1 calc R . . C13 C 0.1319(2) 0.35441(17) 0.78611(19) 0.0766(6) Uani 1 1 d . . . H13 H 0.0719 0.3480 0.8245 0.092 Uiso 1 1 calc R . . C14 C 0.2026(2) 0.27825(17) 0.7980(2) 0.0900(8) Uani 1 1 d . . . H14 H 0.1916 0.2199 0.8451 0.108 Uiso 1 1 calc R . . C15 C 0.2901(2) 0.28741(15) 0.7403(3) 0.0900(8) Uani 1 1 d . . . H15 H 0.3388 0.2349 0.7483 0.108 Uiso 1 1 calc R . . C16 C 0.30739(15) 0.37389(13) 0.6702(2) 0.0654(5) Uani 1 1 d . . . H16 H 0.3669 0.3792 0.6303 0.078 Uiso 1 1 calc R . . C17 C 0.26736(11) 0.63674(11) 0.68572(15) 0.0449(3) Uani 1 1 d . . . H17A H 0.2742 0.6974 0.6337 0.054 Uiso 1 1 calc R . . H17B H 0.2048 0.6441 0.7257 0.054 Uiso 1 1 calc R . . C18 C 0.36301(12) 0.62789(12) 0.80054(15) 0.0491(4) Uani 1 1 d . . . H18A H 0.3550 0.5693 0.8559 0.059 Uiso 1 1 calc R . . H18B H 0.4257 0.6180 0.7613 0.059 Uiso 1 1 calc R . . C19 C 0.37826(15) 0.71821(16) 0.8904(2) 0.0718(6) Uani 1 1 d . . . H19A H 0.3154 0.7273 0.9295 0.086 Uiso 1 1 calc R . . H19B H 0.3846 0.7766 0.8340 0.086 Uiso 1 1 calc R . . C20 C 0.47287(15) 0.71415(17) 1.0052(2) 0.0749(6) Uani 1 1 d . . . H20A H 0.4678 0.6564 1.0617 0.112 Uiso 1 1 calc R . . H20B H 0.4756 0.7740 1.0600 0.112 Uiso 1 1 calc R . . H20C H 0.5361 0.7095 0.9678 0.112 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 0.0401(5) 0.0563(6) 0.0426(6) -0.0070(4) 0.0090(4) -0.0008(4) O2 0.0453(5) 0.0476(6) 0.0465(6) 0.0014(4) 0.0123(4) 0.0066(4) O3 0.0548(7) 0.0812(9) 0.0552(7) 0.0014(6) 0.0196(6) 0.0076(6) C1 0.0395(7) 0.0459(8) 0.0400(7) -0.0011(6) 0.0104(6) -0.0011(6) C2 0.0431(7) 0.0436(8) 0.0420(8) 0.0012(6) 0.0080(6) -0.0009(6) C3 0.0492(8) 0.0397(7) 0.0406(8) -0.0004(6) 0.0086(6) 0.0001(6) C4 0.0483(8) 0.0407(7) 0.0409(8) -0.0029(6) 0.0103(6) -0.0011(6) C5 0.0545(9) 0.0503(9) 0.0539(9) -0.0050(7) 0.0176(7) 0.0026(7) C6 0.0751(11) 0.0565(10) 0.0494(9) -0.0029(7) 0.0243(8) 0.0088(8) C7 0.0818(12) 0.0617(10) 0.0407(9) -0.0059(7) 0.0090(8) 0.0078(9) C8 0.0594(9) 0.0532(9) 0.0442(8) -0.0040(7) 0.0046(7) 0.0024(7) C9 0.0448(8) 0.0623(10) 0.0422(8) -0.0063(7) 0.0065(6) 0.0075(7) C10 0.0688(11) 0.0612(11) 0.0630(11) -0.0061(8) 0.0110(9) 0.0174(9) C11 0.0544(8) 0.0452(8) 0.0383(7) -0.0021(6) 0.0007(6) -0.0067(6) C12 0.0723(11) 0.0628(10) 0.0426(9) 0.0003(7) 0.0130(8) -0.0139(8) C13 0.1052(16) 0.0748(13) 0.0478(10) 0.0056(9) 0.0105(10) -0.0338(12) C14 0.122(2) 0.0694(14) 0.0656(13) 0.0194(10) -0.0141(13) -0.0392(14) C15 0.0994(17) 0.0478(11) 0.1039(18) 0.0093(11) -0.0255(14) -0.0017(10) C16 0.0663(11) 0.0476(9) 0.0757(12) 0.0020(8) -0.0021(9) -0.0014(8) C17 0.0470(8) 0.0442(8) 0.0439(8) -0.0031(6) 0.0103(6) 0.0001(6) C18 0.0510(8) 0.0486(8) 0.0459(8) -0.0058(7) 0.0053(7) 0.0006(7) C19 0.0649(11) 0.0739(12) 0.0700(12) -0.0301(10) -0.0027(9) 0.0100(9) C20 0.0677(11) 0.0830(14) 0.0678(12) -0.0300(10) -0.0017(9) 0.0006(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.3652(17) . ? O1 C1 1.4694(16) . ? O2 C9 1.3492(18) . ? O2 C2 1.4559(17) . ? O3 C9 1.2033(19) . ? C1 C11 1.520(2) . ? C1 C17 1.523(2) . ? C1 C2 1.5593(19) . ? C2 C3 1.495(2) . ? C2 H2 0.9900 . ? C3 C8 1.381(2) . ? C3 C4 1.383(2) . ? C4 C5 1.386(2) . ? C5 C6 1.380(2) . ? C5 H5 0.9400 . ? C6 C7 1.387(3) . ? C6 H6 0.9400 . ? C7 C8 1.384(2) . ? C7 H7 0.9400 . ? C8 H8 0.9400 . ? C9 C10 1.492(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? C11 C16 1.386(2) . ? C11 C12 1.397(2) . ? C12 C13 1.379(3) . ? C12 H12 0.9400 . ? C13 C14 1.364(4) . ? C13 H13 0.9400 . ? C14 C15 1.380(4) . ? C14 H14 0.9400 . ? C15 C16 1.398(3) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? C17 C18 1.522(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 C19 1.500(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C19 C20 1.509(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 H20C 0.9700 . ? 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 C4 O1 C1 107.82(10) . . ? C9 O2 C2 117.79(12) . . ? O1 C1 C11 109.05(11) . . ? O1 C1 C17 106.22(11) . . ? C11 C1 C17 112.09(12) . . ? O1 C1 C2 104.76(10) . . ? C11 C1 C2 108.74(11) . . ? C17 C1 C2 115.53(12) . . ? O2 C2 C3 106.07(11) . . ? O2 C2 C1 113.67(11) . . ? C3 C2 C1 102.13(11) . . ? O2 C2 H2 111.5 . . ? C3 C2 H2 111.5 . . ? C1 C2 H2 111.5 . . ? C8 C3 C4 119.98(14) . . ? C8 C3 C2 131.44(14) . . ? C4 C3 C2 108.31(12) . . ? O1 C4 C3 113.32(12) . . ? O1 C4 C5 124.21(14) . . ? C3 C4 C5 122.45(14) . . ? C6 C5 C4 116.77(15) . . ? C6 C5 H5 121.6 . . ? C4 C5 H5 121.6 . . ? C5 C6 C7 121.67(15) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C8 C7 C6 120.62(16) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C3 C8 C7 118.52(16) . . ? C3 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? O3 C9 O2 123.70(15) . . ? O3 C9 C10 126.24(15) . . ? O2 C9 C10 110.06(14) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 118.75(16) . . ? C16 C11 C1 122.50(15) . . ? C12 C11 C1 118.75(14) . . ? C13 C12 C11 120.7(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.7(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.55(19) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 120.8(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C11 C16 C15 119.6(2) . . ? C11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C18 C17 C1 114.47(12) . . ? C18 C17 H17A 108.6 . . ? C1 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C1 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C19 C18 C17 112.40(13) . . ? C19 C18 H18A 109.1 . . ? C17 C18 H18A 109.1 . . ? C19 C18 H18B 109.1 . . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C18 C19 C20 114.75(16) . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19B 108.6 . . ? C20 C19 H19B 108.6 . . ? H19A C19 H19B 107.6 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 O1 C1 C11 98.81(13) . . . . ? C4 O1 C1 C17 -140.20(12) . . . . ? C4 O1 C1 C2 -17.46(14) . . . . ? C9 O2 C2 C3 157.29(12) . . . . ? C9 O2 C2 C1 -91.30(14) . . . . ? O1 C1 C2 O2 -95.23(13) . . . . ? C11 C1 C2 O2 148.30(12) . . . . ? C17 C1 C2 O2 21.26(17) . . . . ? O1 C1 C2 C3 18.56(13) . . . . ? C11 C1 C2 C3 -97.92(13) . . . . ? C17 C1 C2 C3 135.05(12) . . . . ? O2 C2 C3 C8 -68.3(2) . . . . ? C1 C2 C3 C8 172.45(16) . . . . ? O2 C2 C3 C4 105.55(13) . . . . ? C1 C2 C3 C4 -13.74(15) . . . . ? C1 O1 C4 C3 9.33(16) . . . . ? C1 O1 C4 C5 -172.52(14) . . . . ? C8 C3 C4 O1 178.16(13) . . . . ? C2 C3 C4 O1 3.52(17) . . . . ? C8 C3 C4 C5 0.0(2) . . . . ? C2 C3 C4 C5 -174.67(14) . . . . ? O1 C4 C5 C6 -177.52(14) . . . . ? C3 C4 C5 C6 0.5(2) . . . . ? C4 C5 C6 C7 -0.8(2) . . . . ? C5 C6 C7 C8 0.7(3) . . . . ? C4 C3 C8 C7 -0.1(2) . . . . ? C2 C3 C8 C7 173.10(16) . . . . ? C6 C7 C8 C3 -0.2(3) . . . . ? C2 O2 C9 O3 3.2(2) . . . . ? C2 O2 C9 C10 -177.72(12) . . . . ? O1 C1 C11 C16 2.44(19) . . . . ? C17 C1 C11 C16 -114.89(16) . . . . ? C2 C1 C11 C16 116.13(16) . . . . ? O1 C1 C11 C12 -177.90(12) . . . . ? C17 C1 C11 C12 64.77(17) . . . . ? C2 C1 C11 C12 -64.20(17) . . . . ? C16 C11 C12 C13 0.5(2) . . . . ? C1 C11 C12 C13 -179.13(15) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C12 C13 C14 C15 -0.6(3) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C12 C11 C16 C15 -1.0(3) . . . . ? C1 C11 C16 C15 178.62(16) . . . . ? C14 C15 C16 C11 0.7(3) . . . . ? O1 C1 C17 C18 -58.84(15) . . . . ? C11 C1 C17 C18 60.17(17) . . . . ? C2 C1 C17 C18 -174.51(12) . . . . ? C1 C17 C18 C19 177.54(15) . . . . ? C17 C18 C19 C20 -179.27(17) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 67.21 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.203 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.031 #============================================================================= # end of cif data for "stu7111" #============================================================================= #============================================================================= # end of cif file #============================================================================= _database_code_depnum_ccdc_archive 'CCDC 963178'