data_publication_text _publ_requested_journal Journal of Organic Chemistry _publ_contact_author_name B.Sridhar _publ_contact_author_address ;Laboratory of X-ray Crystallography Indian Institute of Chemical Technology Hyderabad -500607 ; _publ_contact_author_email sshiya@yahoo.com _publ_contact_author_phone +91-40-27193118 _publ_contact_author_fax +91-40-27193118 loop_ _publ_author_name _publ_author_address 'Kumaraswamy, G' ;Organic -III Indian Institute of Chemical Technology Hyderabad -500607 ; 'Ramakrishna, G' ;Organic Division -III Indian Institute of Chemical Technology Hyderabad -500607 ; 'Naresh, P' ;NMR Division Indian Institute of Chemical Technology Hyderabad -500607 ; 'Jagadeesh, B' ;NMR Division Indian Institute of Chemical Technology Hyderabad -500607 ; 'Sridhar, B' ;Laboratory of X-ray Crystallography Indian Institute of Chemical Technology Hyderabad -500607 ; data_ae60m Compound 9 _audit_creation_method SHELXL-97 _chemical_name_systematic '(2S,4R, 6S)-2(furan-2-yl)-6-phenyl-tetrahydro-2H-pyran-4-ol' _chemical_name_common ? _chemical_formula_moiety 'C15 H16 O3' _chemical_formula_sum 'C15 H16 O3' _chemical_melting_point ? _exptl_crystal_description plates _exptl_crystal_colour colorless _diffrn_ambient_temperature 294(2) _chemical_formula_weight 244.28 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_int_tables_number 4 _chemical_absolute_configuration unk _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.989(3) _cell_length_b 5.0674(14) _cell_length_c 13.200(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.674(4) _cell_angle_gamma 90.00 _cell_volume 649.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2192 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 21.75 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6078 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1277 _reflns_number_gt 1203 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.1460P)^2^+0.3739P] 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 1277 _refine_ls_number_parameters 167 _refine_ls_number_restraints 47 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0925 _refine_ls_wR_factor_ref 0.2512 _refine_ls_wR_factor_gt 0.2472 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.271 _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 C1 C 0.1205(6) 0.3336(14) 0.7876(4) 0.0474(15) Uani 1 1 d . . . H1 H 0.1454 0.1804 0.7506 0.057 Uiso 1 1 calc R . . C2 C 0.2309(7) 0.3709(16) 0.8885(4) 0.0573(17) Uani 1 1 d . . . H2A H 0.2066 0.5190 0.9271 0.069 Uiso 1 1 calc R . . H2B H 0.2359 0.2142 0.9314 0.069 Uiso 1 1 calc R . . C3 C 0.3690(6) 0.4206(13) 0.8650(5) 0.0489(15) Uani 1 1 d . . . H3 H 0.3981 0.2621 0.8334 0.059 Uiso 1 1 calc R . . C4 C 0.3601(7) 0.6481(13) 0.7908(5) 0.0533(16) Uani 1 1 d . . . H4A H 0.4466 0.6644 0.7700 0.064 Uiso 1 1 calc R . . H4B H 0.3453 0.8100 0.8258 0.064 Uiso 1 1 calc R . . C5 C 0.2427(6) 0.6106(13) 0.6937(4) 0.0466(14) Uani 1 1 d . . . H5 H 0.2320 0.7792 0.6562 0.056 Uiso 1 1 calc R . . C6 C 0.2696(5) 0.4019(13) 0.6171(4) 0.0457(14) Uani 1 1 d D . . C7 C 0.3934(6) 0.2797(16) 0.6255(5) 0.0567(17) Uani 1 1 d D . . H7 H 0.4661 0.3223 0.6814 0.068 Uiso 1 1 calc R . . C8 C 0.4146(10) 0.097(2) 0.5546(6) 0.091(3) Uani 1 1 d D . . H8 H 0.5015 0.0234 0.5610 0.109 Uiso 1 1 calc R . . C9 C 0.3095(9) 0.023(3) 0.4757(6) 0.098(4) Uani 1 1 d D . . H9 H 0.3196 -0.1103 0.4297 0.118 Uiso 1 1 calc R . . C10 C 0.1877(9) 0.152(2) 0.4662(6) 0.088(3) Uani 1 1 d D . . H10 H 0.1167 0.1139 0.4086 0.106 Uiso 1 1 calc R . . C11 C 0.1632(6) 0.3330(18) 0.5354(4) 0.066(2) Uani 1 1 d D . . H11 H 0.0764 0.4081 0.5276 0.079 Uiso 1 1 calc R . . C12 C -0.0197(7) 0.2909(19) 0.8040(5) 0.0610(17) Uani 1 1 d U . . C13 C -0.1030(9) 0.117(3) 0.7525(9) 0.112(4) Uani 1 1 d U . . H13 H -0.0902 0.0038 0.7000 0.135 Uiso 1 1 calc R . . C14 C -0.2274(12) 0.143(5) 0.7996(12) 0.150(5) Uani 1 1 d U . . H14 H -0.3015 0.0265 0.7859 0.179 Uiso 1 1 calc R . . C15 C -0.2187(12) 0.344(5) 0.8606(8) 0.141(5) Uani 1 1 d U . . H15 H -0.2834 0.4103 0.8942 0.170 Uiso 1 1 calc R . . O1 O 0.1162(4) 0.5631(9) 0.7224(3) 0.0488(12) Uani 1 1 d . . . O2 O 0.4712(5) 0.4856(12) 0.9580(4) 0.0725(17) Uani 1 1 d . . . H2O H 0.503(10) 0.362(18) 0.996(8) 0.06(2) Uiso 1 1 d . . . O3 O -0.0808(9) 0.439(3) 0.8628(8) 0.151(4) Uani 1 1 d U . . 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 0.052(3) 0.055(4) 0.034(2) -0.005(3) 0.007(2) 0.012(3) C2 0.072(4) 0.056(4) 0.037(3) 0.000(3) 0.000(3) 0.001(3) C3 0.056(3) 0.040(3) 0.042(3) 0.002(3) -0.007(3) 0.002(3) C4 0.065(4) 0.036(4) 0.052(3) 0.000(3) 0.000(3) -0.001(3) C5 0.058(3) 0.036(3) 0.043(3) 0.011(3) 0.006(2) 0.009(3) C6 0.050(3) 0.048(4) 0.040(3) 0.006(3) 0.012(2) -0.006(3) C7 0.053(3) 0.069(5) 0.053(3) -0.005(4) 0.022(3) -0.001(3) C8 0.096(6) 0.095(7) 0.089(6) -0.003(6) 0.039(5) 0.002(6) C9 0.095(6) 0.130(10) 0.073(5) 0.015(7) 0.024(5) -0.021(7) C10 0.082(5) 0.127(9) 0.051(4) -0.021(5) 0.007(4) -0.019(6) C11 0.053(3) 0.097(6) 0.041(3) -0.005(4) -0.003(3) -0.003(4) C12 0.060(3) 0.079(5) 0.045(3) 0.005(3) 0.014(2) 0.007(3) C13 0.070(5) 0.126(9) 0.138(8) -0.048(6) 0.019(5) -0.010(5) C14 0.063(4) 0.192(12) 0.191(11) 0.011(9) 0.024(6) -0.014(6) C15 0.107(5) 0.249(13) 0.090(6) 0.023(8) 0.066(5) 0.040(8) O1 0.051(2) 0.052(3) 0.0403(19) 0.004(2) 0.0047(16) 0.016(2) O2 0.083(3) 0.053(3) 0.057(3) 0.001(3) -0.032(2) -0.003(3) O3 0.117(5) 0.189(9) 0.157(6) -0.084(6) 0.050(5) 0.000(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 O1 1.441(8) . ? C1 C12 1.483(9) . ? C1 C2 1.527(8) . ? C1 H1 0.9800 . ? C2 C3 1.505(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O2 1.438(7) . ? C3 C4 1.502(9) . ? C3 H3 0.9800 . ? C4 C5 1.531(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O1 1.422(7) . ? C5 C6 1.530(9) . ? C5 H5 0.9800 . ? C6 C7 1.364(7) . ? C6 C11 1.368(7) . ? C7 C8 1.369(8) . ? C7 H7 0.9300 . ? C8 C9 1.345(9) . ? C8 H8 0.9300 . ? C9 C10 1.361(9) . ? C9 H9 0.9300 . ? C10 C11 1.356(8) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.291(15) . ? C12 O3 1.328(12) . ? C13 C14 1.521(16) . ? C13 H13 0.9300 . ? C14 C15 1.29(2) . ? C14 H14 0.9300 . ? C15 O3 1.453(17) . ? C15 H15 0.9300 . ? O2 H2O 0.82(10) . ? 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 C12 108.0(5) . . ? O1 C1 C2 109.5(5) . . ? C12 C1 C2 113.8(5) . . ? O1 C1 H1 108.5 . . ? C12 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? C3 C2 C1 110.4(5) . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? O2 C3 C4 107.6(5) . . ? O2 C3 C2 111.3(5) . . ? C4 C3 C2 110.3(5) . . ? O2 C3 H3 109.2 . . ? C4 C3 H3 109.2 . . ? C2 C3 H3 109.2 . . ? C3 C4 C5 111.5(5) . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? O1 C5 C6 111.4(5) . . ? O1 C5 C4 110.5(4) . . ? C6 C5 C4 114.8(5) . . ? O1 C5 H5 106.5 . . ? C6 C5 H5 106.5 . . ? C4 C5 H5 106.5 . . ? C7 C6 C11 118.0(6) . . ? C7 C6 C5 123.9(5) . . ? C11 C6 C5 118.1(5) . . ? C6 C7 C8 122.4(7) . . ? C6 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C9 C8 C7 119.9(9) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 117.0(10) . . ? C8 C9 H9 121.5 . . ? C10 C9 H9 121.5 . . ? C11 C10 C9 124.3(8) . . ? C11 C10 H10 117.9 . . ? C9 C10 H10 117.9 . . ? C10 C11 C6 118.2(6) . . ? C10 C11 H11 120.9 . . ? C6 C11 H11 120.9 . . ? C13 C12 O3 111.5(8) . . ? C13 C12 C1 122.4(8) . . ? O3 C12 C1 125.7(9) . . ? C12 C13 C14 102.2(11) . . ? C12 C13 H13 128.9 . . ? C14 C13 H13 128.9 . . ? C15 C14 C13 112.5(14) . . ? C15 C14 H14 123.7 . . ? C13 C14 H14 123.7 . . ? C14 C15 O3 101.5(10) . . ? C14 C15 H15 129.3 . . ? O3 C15 H15 129.3 . . ? C5 O1 C1 113.1(4) . . ? C3 O2 H2O 117(7) . . ? C12 O3 C15 111.4(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -57.4(7) . . . . ? C12 C1 C2 C3 -178.4(7) . . . . ? C1 C2 C3 O2 173.5(6) . . . . ? C1 C2 C3 C4 54.2(7) . . . . ? O2 C3 C4 C5 -173.9(5) . . . . ? C2 C3 C4 C5 -52.3(7) . . . . ? C3 C4 C5 O1 54.0(7) . . . . ? C3 C4 C5 C6 -73.1(7) . . . . ? O1 C5 C6 C7 -134.7(6) . . . . ? C4 C5 C6 C7 -8.1(9) . . . . ? O1 C5 C6 C11 45.1(7) . . . . ? C4 C5 C6 C11 171.7(6) . . . . ? C11 C6 C7 C8 1.2(11) . . . . ? C5 C6 C7 C8 -179.0(7) . . . . ? C6 C7 C8 C9 -3.0(13) . . . . ? C7 C8 C9 C10 4.9(15) . . . . ? C8 C9 C10 C11 -5.5(16) . . . . ? C9 C10 C11 C6 3.8(14) . . . . ? C7 C6 C11 C10 -1.6(11) . . . . ? C5 C6 C11 C10 178.6(7) . . . . ? O1 C1 C12 C13 100.6(11) . . . . ? C2 C1 C12 C13 -137.6(10) . . . . ? O1 C1 C12 O3 -71.9(10) . . . . ? C2 C1 C12 O3 49.9(11) . . . . ? O3 C12 C13 C14 -8.6(15) . . . . ? C1 C12 C13 C14 178.0(10) . . . . ? C12 C13 C14 C15 9.2(17) . . . . ? C13 C14 C15 O3 -5.5(17) . . . . ? C6 C5 O1 C1 70.1(5) . . . . ? C4 C5 O1 C1 -58.8(6) . . . . ? C12 C1 O1 C5 -174.8(5) . . . . ? C2 C1 O1 C5 60.8(6) . . . . ? C13 C12 O3 C15 6.0(16) . . . . ? C1 C12 O3 C15 179.2(9) . . . . ? C14 C15 O3 C12 0.2(16) . . . . ? 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 H2O O2 0.82(10) 2.00(10) 2.771(4) 157(10) 2_647 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.463 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.072 #===end data_ae71m Compound 7 _audit_creation_method SHELXL-97 _chemical_name_systematic '(S)-2(furan-2-yl)-2,3-dihydropyran-4 -one' _chemical_name_common ? _chemical_formula_moiety 'C9 H8 O3' _chemical_formula_sum 'C9 H8 O3' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour colorless _diffrn_ambient_temperature 294(2) _chemical_formula_weight 164.15 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_int_tables_number 1 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.4661(18) _cell_length_b 8.347(3) _cell_length_c 9.739(3) _cell_angle_alpha 67.537(5) _cell_angle_beta 78.265(5) _cell_angle_gamma 84.030(5) _cell_volume 401.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2551 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 27.31 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 172 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3897 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1411 _reflns_number_gt 1374 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0581P)^2^+0.0566P] 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 1411 _refine_ls_number_parameters 217 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0945 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.072 _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 C1 C 0.3765(6) 0.7410(4) 0.8032(4) 0.0562(7) Uani 1 1 d . . . C2 C 0.1917(8) 0.6589(7) 0.9083(5) 0.0863(12) Uani 1 1 d . . . H2 H 0.0856 0.5825 0.9025 0.104 Uiso 1 1 calc R . . C3 C 0.1855(11) 0.7095(7) 1.0327(5) 0.0937(15) Uani 1 1 d . . . H3 H 0.0779 0.6689 1.1252 0.112 Uiso 1 1 calc R . . C4 C 0.3504(12) 0.8182(7) 0.9955(6) 0.0977(15) Uani 1 1 d . . . H4 H 0.3828 0.8742 1.0558 0.117 Uiso 1 1 calc R . . C5 C 0.4751(6) 0.7392(4) 0.6510(3) 0.0486(6) Uani 1 1 d . . . H5 H 0.4042 0.6410 0.6424 0.058 Uiso 1 1 calc R . . C6 C 0.4887(6) 0.9317(4) 0.3980(4) 0.0569(8) Uani 1 1 d . . . H6 H 0.4070 1.0123 0.3244 0.068 Uiso 1 1 calc R . . C7 C 0.7000(6) 0.8569(4) 0.3511(4) 0.0570(7) Uani 1 1 d . . . H7 H 0.7502 0.8793 0.2485 0.068 Uiso 1 1 calc R . . C8 C 0.8502(5) 0.7437(4) 0.4545(4) 0.0539(7) Uani 1 1 d . . . C9 C 0.7558(6) 0.7219(4) 0.6168(4) 0.0526(7) Uani 1 1 d . . . H9A H 0.8287 0.8088 0.6386 0.063 Uiso 1 1 calc R . . H9B H 0.8092 0.6086 0.6818 0.063 Uiso 1 1 calc R . . O1 O 0.4793(8) 0.8435(5) 0.8500(4) 0.1073(12) Uani 1 1 d . . . O2 O 0.3853(4) 0.8995(3) 0.5427(2) 0.0534(5) Uani 1 1 d . . . O3 O 1.0476(5) 0.6762(4) 0.4160(3) 0.0768(8) Uani 1 1 d . . . C10 C 0.7205(5) 0.2429(4) 0.7324(3) 0.0435(6) Uani 1 1 d . . . C11 C 0.5760(7) 0.2456(5) 0.9581(4) 0.0683(10) Uani 1 1 d . . . H11 H 0.4662 0.2527 1.0422 0.082 Uiso 1 1 calc R . . C12 C 0.8173(7) 0.2232(5) 0.9486(4) 0.0642(9) Uani 1 1 d . . . H12 H 0.9085 0.2109 1.0231 0.077 Uiso 1 1 calc R . . C13 C 0.9144(6) 0.2210(5) 0.8023(4) 0.0593(8) Uani 1 1 d . . . H13 H 1.0815 0.2071 0.7628 0.071 Uiso 1 1 calc R . . C14 C 0.6943(5) 0.2511(3) 0.5819(3) 0.0394(5) Uani 1 1 d . . . H14 H 0.5979 0.1520 0.5949 0.047 Uiso 1 1 calc R . . C15 C 0.5483(5) 0.4527(4) 0.3683(3) 0.0462(6) Uani 1 1 d . . . H15 H 0.4272 0.5341 0.3276 0.055 Uiso 1 1 calc R . . C16 C 0.7028(6) 0.3889(4) 0.2754(3) 0.0497(7) Uani 1 1 d . . . H16 H 0.6720 0.4146 0.1786 0.060 Uiso 1 1 calc R . . C17 C 0.9160(5) 0.2811(4) 0.3227(3) 0.0470(6) Uani 1 1 d . . . C18 C 0.9437(5) 0.2453(4) 0.4824(3) 0.0436(6) Uani 1 1 d . . . H18A H 1.0511 0.3306 0.4827 0.052 Uiso 1 1 calc R . . H18B H 1.0231 0.1318 0.5234 0.052 Uiso 1 1 calc R . . O4 O 0.5057(4) 0.2575(3) 0.8265(2) 0.0604(6) Uani 1 1 d . . . O5 O 0.5521(3) 0.4099(2) 0.5147(2) 0.0461(5) Uani 1 1 d . . . O6 O 1.0736(4) 0.2301(3) 0.2393(3) 0.0664(7) 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 0.0613(19) 0.0503(17) 0.0558(18) -0.0220(14) -0.0073(14) 0.0061(14) C2 0.068(2) 0.112(3) 0.089(3) -0.058(3) 0.013(2) -0.022(2) C3 0.121(4) 0.087(3) 0.055(2) -0.023(2) 0.015(2) 0.002(3) C4 0.140(5) 0.098(3) 0.075(3) -0.053(3) -0.024(3) 0.006(3) C5 0.0506(16) 0.0427(14) 0.0516(16) -0.0185(12) -0.0066(12) 0.0021(11) C6 0.0588(18) 0.0559(17) 0.0519(18) -0.0158(14) -0.0144(13) 0.0083(14) C7 0.0556(17) 0.0590(17) 0.0518(17) -0.0219(14) 0.0006(13) 0.0041(14) C8 0.0419(16) 0.0509(16) 0.068(2) -0.0260(14) -0.0024(13) 0.0018(12) C9 0.0471(16) 0.0524(16) 0.0585(18) -0.0208(13) -0.0142(13) 0.0087(12) O1 0.136(3) 0.107(2) 0.095(2) -0.062(2) 0.014(2) -0.044(2) O2 0.0511(11) 0.0555(12) 0.0522(12) -0.0222(9) -0.0112(9) 0.0170(9) O3 0.0486(13) 0.0847(17) 0.0934(19) -0.0414(15) 0.0043(12) 0.0129(12) C10 0.0386(13) 0.0477(14) 0.0427(15) -0.0172(12) -0.0034(11) -0.0005(11) C11 0.076(2) 0.090(3) 0.0384(16) -0.0273(17) -0.0027(15) -0.0030(19) C12 0.068(2) 0.083(2) 0.0481(17) -0.0267(16) -0.0220(15) 0.0042(17) C13 0.0466(16) 0.084(2) 0.0500(17) -0.0269(16) -0.0125(13) 0.0025(15) C14 0.0359(12) 0.0416(13) 0.0422(14) -0.0173(11) -0.0084(10) 0.0014(10) C15 0.0397(14) 0.0518(15) 0.0453(15) -0.0149(12) -0.0136(11) 0.0062(11) C16 0.0479(15) 0.0635(18) 0.0409(14) -0.0226(13) -0.0122(12) 0.0060(13) C17 0.0463(15) 0.0549(15) 0.0421(14) -0.0232(13) -0.0055(11) 0.0039(12) C18 0.0382(14) 0.0493(15) 0.0441(15) -0.0196(12) -0.0100(11) 0.0099(11) O4 0.0446(11) 0.0924(16) 0.0452(11) -0.0305(11) -0.0021(9) 0.0021(10) O5 0.0409(10) 0.0547(11) 0.0437(11) -0.0224(9) -0.0080(8) 0.0118(8) O6 0.0583(13) 0.0923(17) 0.0527(13) -0.0388(12) -0.0076(10) 0.0229(12) _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 1.314(6) . ? C1 O1 1.325(5) . ? C1 C5 1.476(4) . ? C2 C3 1.421(7) . ? C2 H2 0.9300 . ? C3 C4 1.246(8) . ? C3 H3 0.9300 . ? C4 O1 1.395(6) . ? C4 H4 0.9300 . ? C5 O2 1.463(4) . ? C5 C9 1.507(4) . ? C5 H5 0.9800 . ? C6 C7 1.336(5) . ? C6 O2 1.340(4) . ? C6 H6 0.9300 . ? C7 C8 1.424(5) . ? C7 H7 0.9300 . ? C8 O3 1.222(4) . ? C8 C9 1.505(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C13 1.333(4) . ? C10 O4 1.361(3) . ? C10 C14 1.477(4) . ? C11 C12 1.302(5) . ? C11 O4 1.376(4) . ? C11 H11 0.9300 . ? C12 C13 1.422(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O5 1.456(3) . ? C14 C18 1.511(3) . ? C14 H14 0.9800 . ? C15 C16 1.334(4) . ? C15 O5 1.335(3) . ? C15 H15 0.9300 . ? C16 C17 1.437(4) . ? C16 H16 0.9300 . ? C17 O6 1.219(4) . ? C17 C18 1.505(4) . ? C18 H18A 0.9700 . ? C18 H18B 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 C2 C1 O1 109.5(3) . . ? C2 C1 C5 131.6(4) . . ? O1 C1 C5 118.9(3) . . ? C1 C2 C3 106.6(4) . . ? C1 C2 H2 126.7 . . ? C3 C2 H2 126.7 . . ? C4 C3 C2 107.6(4) . . ? C4 C3 H3 126.2 . . ? C2 C3 H3 126.2 . . ? C3 C4 O1 110.0(4) . . ? C3 C4 H4 125.0 . . ? O1 C4 H4 125.0 . . ? O2 C5 C1 107.1(2) . . ? O2 C5 C9 110.8(2) . . ? C1 C5 C9 113.8(3) . . ? O2 C5 H5 108.3 . . ? C1 C5 H5 108.3 . . ? C9 C5 H5 108.3 . . ? C7 C6 O2 125.1(3) . . ? C7 C6 H6 117.4 . . ? O2 C6 H6 117.4 . . ? C6 C7 C8 121.6(3) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? O3 C8 C7 123.6(3) . . ? O3 C8 C9 121.6(3) . . ? C7 C8 C9 114.6(3) . . ? C8 C9 C5 112.0(3) . . ? C8 C9 H9A 109.2 . . ? C5 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? C5 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C1 O1 C4 106.2(4) . . ? C6 O2 C5 114.9(2) . . ? C13 C10 O4 109.4(3) . . ? C13 C10 C14 134.0(3) . . ? O4 C10 C14 116.5(2) . . ? C12 C11 O4 110.7(3) . . ? C12 C11 H11 124.6 . . ? O4 C11 H11 124.6 . . ? C11 C12 C13 106.7(3) . . ? C11 C12 H12 126.6 . . ? C13 C12 H12 126.6 . . ? C10 C13 C12 107.0(3) . . ? C10 C13 H13 126.5 . . ? C12 C13 H13 126.5 . . ? O5 C14 C10 106.9(2) . . ? O5 C14 C18 111.5(2) . . ? C10 C14 C18 112.5(2) . . ? O5 C14 H14 108.6 . . ? C10 C14 H14 108.6 . . ? C18 C14 H14 108.6 . . ? C16 C15 O5 125.8(3) . . ? C16 C15 H15 117.1 . . ? O5 C15 H15 117.1 . . ? C15 C16 C17 120.9(3) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? O6 C17 C16 123.7(3) . . ? O6 C17 C18 121.3(3) . . ? C16 C17 C18 114.8(2) . . ? C17 C18 C14 111.8(2) . . ? C17 C18 H18A 109.3 . . ? C14 C18 H18A 109.3 . . ? C17 C18 H18B 109.3 . . ? C14 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? C10 O4 C11 106.1(2) . . ? C15 O5 C14 114.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -2.4(5) . . . . ? C5 C1 C2 C3 179.2(4) . . . . ? C1 C2 C3 C4 2.5(6) . . . . ? C2 C3 C4 O1 -1.7(7) . . . . ? C2 C1 C5 O2 103.3(5) . . . . ? O1 C1 C5 O2 -75.0(4) . . . . ? C2 C1 C5 C9 -133.9(5) . . . . ? O1 C1 C5 C9 47.8(4) . . . . ? O2 C6 C7 C8 -5.7(5) . . . . ? C6 C7 C8 O3 -178.1(3) . . . . ? C6 C7 C8 C9 -2.1(5) . . . . ? O3 C8 C9 C5 -153.2(3) . . . . ? C7 C8 C9 C5 30.7(4) . . . . ? O2 C5 C9 C8 -51.9(3) . . . . ? C1 C5 C9 C8 -172.6(2) . . . . ? C2 C1 O1 C4 1.4(5) . . . . ? C5 C1 O1 C4 -179.9(4) . . . . ? C3 C4 O1 C1 0.2(6) . . . . ? C7 C6 O2 C5 -17.4(5) . . . . ? C1 C5 O2 C6 170.2(3) . . . . ? C9 C5 O2 C6 45.6(3) . . . . ? O4 C11 C12 C13 0.4(5) . . . . ? O4 C10 C13 C12 -0.4(4) . . . . ? C14 C10 C13 C12 -179.3(3) . . . . ? C11 C12 C13 C10 0.0(4) . . . . ? C13 C10 C14 O5 -127.6(4) . . . . ? O4 C10 C14 O5 53.6(3) . . . . ? C13 C10 C14 C18 -4.9(5) . . . . ? O4 C10 C14 C18 176.3(2) . . . . ? O5 C15 C16 C17 -8.6(5) . . . . ? C15 C16 C17 O6 -174.3(3) . . . . ? C15 C16 C17 C18 1.2(4) . . . . ? O6 C17 C18 C14 -156.3(3) . . . . ? C16 C17 C18 C14 28.1(3) . . . . ? O5 C14 C18 C17 -51.1(3) . . . . ? C10 C14 C18 C17 -171.3(2) . . . . ? C13 C10 O4 C11 0.7(4) . . . . ? C14 C10 O4 C11 179.8(3) . . . . ? C12 C11 O4 C10 -0.7(4) . . . . ? C16 C15 O5 C14 -16.2(4) . . . . ? C10 C14 O5 C15 169.0(2) . . . . ? C18 C14 O5 C15 45.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.314 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.031 #===end