# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jonathan Percy' 'Christophe Audouard' 'Igor Barsukov' 'John Fawcett' 'Gerry A. Griffith' 'Stephane Pintat' 'Clive A. Smith' _publ_contact_author_name 'Prof Jonathan Percy' _publ_contact_author_address ; Department of Chemistry University of Leicester University Road Leicester LE1 7RH UNITED KINGDOM ; _publ_contact_author_email JMP29@LE.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; A Stereodivergent Asymmetric Approach to Difluorinated Aldonic Acids ; data_7b _database_code_depnum_ccdc_archive 'CCDC 235709' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 F2 O4' _chemical_formula_weight 328.35 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.7774(6) _cell_length_b 11.6322(7) _cell_length_c 14.7974(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1682.95(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6315 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 28.04 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 11573 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2966 _reflns_number_gt 2812 _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^)+(0.0416P)^2^+0.1247P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(6) _refine_ls_number_reflns 2966 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 F1 F 0.27603(9) 0.40180(9) 0.85058(6) 0.0411(3) Uani 1 1 d . . . F2 F 0.16097(11) 0.54593(8) 0.79471(6) 0.0445(3) Uani 1 1 d . . . O1 O 0.07705(11) 0.33274(10) 0.60490(6) 0.0321(3) Uani 1 1 d . . . O2 O -0.03653(10) 0.39961(9) 0.72794(7) 0.0330(3) Uani 1 1 d . . . O3 O 0.06105(12) 0.33811(9) 0.95646(6) 0.0338(3) Uani 1 1 d . . . O4 O 0.11621(17) 0.46398(11) 1.06618(8) 0.0574(4) Uani 1 1 d . . . C1 C 0.17967(14) 0.34552(12) 0.67352(9) 0.0266(3) Uani 1 1 d . . . H1 H 0.2331 0.4177 0.6634 0.032 Uiso 1 1 calc R . . C2 C -0.03578(16) 0.40247(14) 0.63021(10) 0.0319(4) Uani 1 1 d . . . C2A C -0.0189(2) 0.52427(15) 0.59820(12) 0.0435(4) Uani 1 1 d . . . H2A1 H -0.0189 0.5259 0.5320 0.065 Uiso 1 1 calc R . . H2A2 H 0.0678 0.5552 0.6208 0.065 Uiso 1 1 calc R . . H2A3 H -0.0947 0.5712 0.6210 0.065 Uiso 1 1 calc R . . C2B C -0.16444(17) 0.34574(16) 0.59666(12) 0.0437(4) Uani 1 1 d . . . H2B1 H -0.1696 0.2672 0.6204 0.065 Uiso 1 1 calc R . . H2B2 H -0.1634 0.3434 0.5305 0.065 Uiso 1 1 calc R . . H2B3 H -0.2441 0.3896 0.6172 0.065 Uiso 1 1 calc R . . C3 C 0.09090(14) 0.35681(13) 0.75863(9) 0.0250(3) Uani 1 1 d . . . H3 H 0.0772 0.2790 0.7859 0.030 Uiso 1 1 calc R . . C4 C 0.14702(15) 0.43727(13) 0.82950(10) 0.0285(3) Uani 1 1 d . . . C5 C 0.06252(17) 0.44703(13) 0.91419(9) 0.0300(3) Uani 1 1 d . . . H5 H -0.0329 0.4707 0.8985 0.036 Uiso 1 1 calc R . . C6 C 0.1204(2) 0.52726(14) 0.98649(10) 0.0452(5) Uani 1 1 d . . . H6A H 0.2155 0.5497 0.9717 0.054 Uiso 1 1 calc R . . H6B H 0.0640 0.5976 0.9918 0.054 Uiso 1 1 calc R . . C7 C 0.05096(18) 0.35741(13) 1.05193(10) 0.0326(4) Uani 1 1 d . . . C7A C 0.1311(2) 0.26616(18) 1.09943(13) 0.0598(6) Uani 1 1 d . . . H7A1 H 0.1254 0.2782 1.1649 0.090 Uiso 1 1 calc R . . H7A2 H 0.2269 0.2699 1.0803 0.090 Uiso 1 1 calc R . . H7A3 H 0.0934 0.1905 1.0843 0.090 Uiso 1 1 calc R . . C7B C -0.0954(2) 0.3631(2) 1.07966(13) 0.0614(6) Uani 1 1 d . . . H7B1 H -0.1424 0.4221 1.0440 0.092 Uiso 1 1 calc R . . H7B2 H -0.1012 0.3828 1.1440 0.092 Uiso 1 1 calc R . . H7B3 H -0.1388 0.2884 1.0693 0.092 Uiso 1 1 calc R . . C8 C 0.27289(14) 0.24305(13) 0.67168(9) 0.0267(3) Uani 1 1 d . . . C9 C 0.41252(15) 0.25661(14) 0.66116(10) 0.0321(3) Uani 1 1 d . . . H9 H 0.4503 0.3315 0.6553 0.039 Uiso 1 1 calc R . . C10 C 0.49742(15) 0.16134(15) 0.65913(11) 0.0382(4) Uani 1 1 d . . . H10 H 0.5932 0.1712 0.6516 0.046 Uiso 1 1 calc R . . C11 C 0.44375(17) 0.05249(15) 0.66796(11) 0.0389(4) Uani 1 1 d . . . H11 H 0.5024 -0.0126 0.6664 0.047 Uiso 1 1 calc R . . C12 C 0.30442(16) 0.03801(14) 0.67912(11) 0.0356(4) Uani 1 1 d . . . H12 H 0.2671 -0.0370 0.6854 0.043 Uiso 1 1 calc R . . C13 C 0.21979(15) 0.13290(13) 0.68113(10) 0.0313(3) Uani 1 1 d . . . H13 H 0.1241 0.1228 0.6891 0.038 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 F1 0.0308(5) 0.0582(6) 0.0343(5) -0.0044(4) -0.0027(4) -0.0073(4) F2 0.0757(7) 0.0297(5) 0.0282(5) 0.0021(4) 0.0036(5) -0.0168(5) O1 0.0362(6) 0.0392(6) 0.0210(5) -0.0036(5) -0.0030(4) 0.0077(5) O2 0.0304(6) 0.0439(7) 0.0248(5) -0.0043(5) -0.0011(5) 0.0074(5) O3 0.0573(7) 0.0252(6) 0.0189(5) -0.0009(4) 0.0063(5) -0.0046(5) O4 0.1062(12) 0.0419(7) 0.0241(6) 0.0012(5) -0.0107(6) -0.0276(7) C1 0.0292(7) 0.0296(8) 0.0210(7) 0.0005(6) -0.0002(6) -0.0015(6) C2 0.0337(8) 0.0368(9) 0.0252(8) -0.0032(6) -0.0032(7) 0.0068(7) C2A 0.0536(11) 0.0386(10) 0.0384(9) 0.0038(8) -0.0046(8) 0.0061(8) C2B 0.0412(10) 0.0473(10) 0.0424(10) -0.0087(8) -0.0106(8) 0.0058(9) C3 0.0279(7) 0.0243(7) 0.0228(7) 0.0007(6) 0.0011(6) -0.0005(6) C4 0.0337(8) 0.0265(8) 0.0254(7) 0.0030(6) -0.0012(7) -0.0052(6) C5 0.0413(9) 0.0253(8) 0.0232(7) -0.0006(6) 0.0003(7) 0.0009(7) C6 0.0791(13) 0.0324(9) 0.0241(8) -0.0014(7) 0.0034(8) -0.0133(9) C7 0.0484(9) 0.0298(8) 0.0197(7) -0.0023(6) 0.0023(7) -0.0025(7) C7A 0.0897(16) 0.0580(12) 0.0319(9) 0.0074(9) 0.0015(10) 0.0219(12) C7B 0.0544(12) 0.0965(17) 0.0332(10) -0.0027(11) 0.0095(9) -0.0019(12) C8 0.0292(7) 0.0343(8) 0.0165(7) -0.0003(6) 0.0007(6) 0.0013(6) C9 0.0303(8) 0.0411(9) 0.0249(8) 0.0010(7) 0.0035(6) -0.0034(7) C10 0.0252(8) 0.0543(11) 0.0352(9) 0.0001(8) 0.0027(7) 0.0012(8) C11 0.0375(9) 0.0431(10) 0.0361(9) -0.0051(8) 0.0010(8) 0.0116(8) C12 0.0373(9) 0.0314(8) 0.0379(9) -0.0051(7) 0.0020(7) 0.0033(7) C13 0.0260(7) 0.0359(9) 0.0320(8) -0.0043(7) 0.0016(7) 0.0002(6) _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 C4 1.3634(17) . ? F2 C4 1.3716(17) . ? O1 C2 1.4196(18) . ? O1 C1 1.4353(17) . ? O2 C3 1.4166(18) . ? O2 C2 1.4466(18) . ? O3 C5 1.4130(18) . ? O3 C7 1.4339(17) . ? O4 C6 1.391(2) . ? O4 C7 1.410(2) . ? C1 C8 1.501(2) . ? C1 C3 1.5351(19) . ? C2 C2A 1.503(2) . ? C2 C2B 1.505(2) . ? C3 C4 1.509(2) . ? C4 C5 1.505(2) . ? C5 C6 1.528(2) . ? C7 C7B 1.490(3) . ? C7 C7A 1.495(2) . ? C8 C9 1.383(2) . ? C8 C13 1.389(2) . ? C9 C10 1.385(2) . ? C10 C11 1.377(3) . ? C11 C12 1.383(2) . ? C12 C13 1.380(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C1 107.30(10) . . ? C3 O2 C2 108.91(11) . . ? C5 O3 C7 107.24(11) . . ? C6 O4 C7 110.60(12) . . ? O1 C1 C8 109.23(11) . . ? O1 C1 C3 101.19(10) . . ? C8 C1 C3 115.23(12) . . ? O1 C2 O2 104.75(12) . . ? O1 C2 C2A 111.73(14) . . ? O2 C2 C2A 109.71(13) . . ? O1 C2 C2B 108.18(13) . . ? O2 C2 C2B 108.39(14) . . ? C2A C2 C2B 113.65(14) . . ? O2 C3 C4 108.94(11) . . ? O2 C3 C1 105.33(10) . . ? C4 C3 C1 114.68(12) . . ? F1 C4 F2 105.83(11) . . ? F1 C4 C5 109.88(12) . . ? F2 C4 C5 107.31(12) . . ? F1 C4 C3 107.92(12) . . ? F2 C4 C3 110.31(12) . . ? C5 C4 C3 115.20(12) . . ? O3 C5 C4 107.84(12) . . ? O3 C5 C6 103.97(12) . . ? C4 C5 C6 115.19(14) . . ? O4 C6 C5 105.04(13) . . ? O4 C7 O3 104.71(12) . . ? O4 C7 C7B 110.73(16) . . ? O3 C7 C7B 110.14(14) . . ? O4 C7 C7A 108.47(15) . . ? O3 C7 C7A 108.43(13) . . ? C7B C7 C7A 113.92(16) . . ? C9 C8 C13 119.03(14) . . ? C9 C8 C1 120.73(14) . . ? C13 C8 C1 120.24(12) . . ? C8 C9 C10 120.19(15) . . ? C11 C10 C9 120.36(14) . . ? C10 C11 C12 119.93(16) . . ? C13 C12 C11 119.74(16) . . ? C12 C13 C8 120.76(14) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.183 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.040 #==END# data_12 _database_code_depnum_ccdc_archive 'CCDC 235710' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H22 F2 O8' _chemical_formula_weight 416.37 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.5206(15) _cell_length_b 5.7277(7) _cell_length_c 15.792(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.137(2) _cell_angle_gamma 90.00 _cell_volume 995.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2471 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 24.87 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details ; absorption correction based on 3913 reflections (SADABS); Rint 0.039 before correction and 0.022 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 7293 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3466 _reflns_number_gt 2916 _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^)+(0.0472P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(9) _refine_ls_number_reflns 3466 _refine_ls_number_parameters 266 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0877 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _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 F1 F 0.92587(14) 0.2239(3) 0.86238(10) 0.0649(5) Uani 1 1 d . . . F2 F 0.89732(14) 0.6008(3) 0.86276(9) 0.0678(5) Uani 1 1 d . . . O1 O 0.70809(13) 0.5871(3) 0.71953(11) 0.0422(4) Uani 1 1 d . . . O2 O 0.57861(17) 0.3672(3) 0.76481(15) 0.0579(6) Uani 1 1 d . . . O3 O 0.93440(13) 0.6184(3) 0.69041(9) 0.0300(4) Uani 1 1 d . . . O4 O 1.03658(14) 0.3997(3) 0.61791(10) 0.0378(4) Uani 1 1 d . . . O5 O 1.14823(14) 0.3097(3) 0.82396(10) 0.0352(4) Uani 1 1 d . . . O6 O 1.27266(16) 0.5858(3) 0.79855(12) 0.0514(5) Uani 1 1 d . . . O7 O 1.2592(2) 0.5247(3) 0.99435(11) 0.0547(5) Uani 1 1 d . . . O9 O 1.1997(3) 0.8952(5) 0.98419(17) 0.1114(11) Uani 1 1 d . . . C1 C 0.7631(2) 0.3787(4) 0.69700(17) 0.0391(6) Uani 1 1 d . . . H1 H 0.7417 0.2440 0.7298 0.047 Uiso 1 1 calc R . . C2 C 0.9007(2) 0.4128(4) 0.72907(15) 0.0348(6) Uani 1 1 d . . . H2 H 0.9391 0.2757 0.7087 0.042 Uiso 1 1 calc R . . C3 C 0.9533(2) 0.4304(5) 0.82845(17) 0.0449(7) Uani 1 1 d . . . C4 C 1.0877(2) 0.4788(5) 0.86344(15) 0.0398(6) Uani 1 1 d . . . H4 H 1.1052 0.6396 0.8457 0.048 Uiso 1 1 calc R . . C5 C 1.1344(3) 0.4549(5) 0.96328(15) 0.0505(7) Uani 1 1 d . . . H5A H 1.0853 0.5537 0.9911 0.061 Uiso 1 1 calc R . . H5B H 1.1265 0.2907 0.9803 0.061 Uiso 1 1 calc R . . C6 C 0.7169(2) 0.3286(4) 0.59931(17) 0.0366(6) Uani 1 1 d . . . C7 C 0.6501(2) 0.4898(5) 0.53884(19) 0.0482(7) Uani 1 1 d . . . H7 H 0.6290 0.6354 0.5590 0.058 Uiso 1 1 calc R . . C8 C 0.6140(2) 0.4390(5) 0.44887(19) 0.0520(7) Uani 1 1 d . . . H8 H 0.5672 0.5492 0.4079 0.062 Uiso 1 1 calc R . . C9 C 0.6455(2) 0.2313(5) 0.41884(18) 0.0504(7) Uani 1 1 d . . . H9 H 0.6234 0.1998 0.3571 0.060 Uiso 1 1 calc R . . C10 C 0.7096(2) 0.0671(5) 0.47895(17) 0.0472(7) Uani 1 1 d . . . H10 H 0.7299 -0.0789 0.4586 0.057 Uiso 1 1 calc R . . C11 C 0.7440(2) 0.1156(5) 0.56815(17) 0.0422(6) Uani 1 1 d . . . H11 H 0.7869 0.0013 0.6091 0.051 Uiso 1 1 calc R . . C12 C 0.6207(2) 0.5546(5) 0.75878(16) 0.0361(6) Uani 1 1 d . . . C13 C 0.5872(2) 0.7778(5) 0.79297(18) 0.0476(7) Uani 1 1 d . . . H13A H 0.6482 0.8174 0.8489 0.071 Uiso 1 1 calc R . . H13B H 0.5076 0.7615 0.8030 0.071 Uiso 1 1 calc R . . H13C H 0.5836 0.9020 0.7496 0.071 Uiso 1 1 calc R . . C14 C 1.00486(18) 0.5881(4) 0.63542(13) 0.0283(5) Uani 1 1 d . . . C15 C 1.0352(2) 0.8135(5) 0.60186(17) 0.0413(6) Uani 1 1 d . . . H15A H 1.1140 0.8009 0.5902 0.062 Uiso 1 1 calc R . . H15B H 1.0394 0.9354 0.6462 0.062 Uiso 1 1 calc R . . H15C H 0.9724 0.8538 0.5469 0.062 Uiso 1 1 calc R . . C16 C 1.2415(2) 0.3843(5) 0.79506(15) 0.0349(6) Uani 1 1 d . . . C17 C 1.2955(2) 0.1898(5) 0.75790(17) 0.0430(6) Uani 1 1 d . . . H17A H 1.3812 0.2236 0.7650 0.064 Uiso 1 1 calc R . . H17B H 1.2520 0.1719 0.6948 0.064 Uiso 1 1 calc R . . H17C H 1.2890 0.0450 0.7893 0.064 Uiso 1 1 calc R . . C18 C 1.2790(5) 0.7567(7) 0.9997(2) 0.0821(13) Uani 1 1 d . . . C19 C 1.4130(4) 0.8069(9) 1.0256(3) 0.128(2) Uani 1 1 d . . . H19A H 1.4266 0.9748 1.0358 0.191 Uiso 1 1 calc R . . H19B H 1.4459 0.7570 0.9779 0.191 Uiso 1 1 calc R . . H19C H 1.4540 0.7215 1.0800 0.191 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 F1 0.0657(11) 0.0778(12) 0.0611(10) 0.0333(9) 0.0341(8) 0.0074(9) F2 0.0755(11) 0.0925(13) 0.0449(9) 0.0025(10) 0.0324(8) 0.0412(11) O1 0.0411(9) 0.0289(9) 0.0668(11) 0.0027(9) 0.0320(8) 0.0044(8) O2 0.0505(12) 0.0393(13) 0.1008(17) -0.0035(11) 0.0486(11) -0.0033(10) O3 0.0322(8) 0.0287(9) 0.0337(8) 0.0041(7) 0.0166(7) 0.0052(7) O4 0.0477(10) 0.0331(10) 0.0396(10) 0.0006(8) 0.0238(8) 0.0044(8) O5 0.0425(9) 0.0320(9) 0.0343(9) 0.0029(7) 0.0161(8) 0.0083(8) O6 0.0561(12) 0.0336(11) 0.0674(13) -0.0032(10) 0.0229(9) -0.0040(10) O7 0.0856(15) 0.0383(11) 0.0321(10) -0.0026(8) 0.0047(9) 0.0085(10) O9 0.232(4) 0.0365(14) 0.0870(19) 0.0019(13) 0.079(2) 0.022(2) C1 0.0423(15) 0.0252(13) 0.0605(17) 0.0067(12) 0.0317(13) 0.0080(12) C2 0.0405(14) 0.0299(13) 0.0417(14) 0.0082(11) 0.0242(11) 0.0077(12) C3 0.0558(18) 0.0451(17) 0.0461(15) 0.0157(13) 0.0340(13) 0.0195(14) C4 0.0559(17) 0.0367(14) 0.0324(13) 0.0053(11) 0.0216(12) 0.0146(12) C5 0.074(2) 0.0469(17) 0.0322(13) 0.0039(13) 0.0186(13) 0.0190(15) C6 0.0278(13) 0.0311(14) 0.0580(17) 0.0040(12) 0.0236(12) -0.0004(10) C7 0.0432(16) 0.0346(14) 0.0721(19) 0.0035(15) 0.0253(14) 0.0024(12) C8 0.0451(16) 0.0478(18) 0.0593(18) 0.0080(15) 0.0093(14) 0.0006(13) C9 0.0387(15) 0.0549(18) 0.0556(18) -0.0034(15) 0.0106(13) -0.0086(14) C10 0.0366(14) 0.0418(16) 0.0643(18) -0.0078(15) 0.0167(13) -0.0032(13) C11 0.0349(13) 0.0347(14) 0.0588(17) 0.0025(13) 0.0166(12) 0.0015(12) C12 0.0263(12) 0.0370(16) 0.0467(14) -0.0020(12) 0.0136(11) 0.0032(12) C13 0.0378(15) 0.0474(17) 0.0588(18) -0.0132(14) 0.0161(13) 0.0044(12) C14 0.0263(11) 0.0328(14) 0.0247(12) -0.0009(11) 0.0056(9) 0.0007(11) C15 0.0394(14) 0.0370(14) 0.0520(16) 0.0062(12) 0.0206(12) 0.0035(12) C16 0.0340(14) 0.0345(16) 0.0331(13) 0.0009(11) 0.0052(11) 0.0021(12) C17 0.0342(14) 0.0419(16) 0.0544(16) -0.0053(12) 0.0156(12) 0.0018(12) C18 0.166(4) 0.047(2) 0.0416(19) -0.0102(16) 0.044(2) -0.011(3) C19 0.174(5) 0.130(4) 0.087(3) -0.047(3) 0.051(3) -0.082(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 F1 C3 1.373(3) . ? F2 C3 1.367(3) . ? O1 C12 1.342(3) . ? O1 C1 1.444(3) . ? O2 C12 1.193(3) . ? O3 C14 1.363(2) . ? O3 C2 1.432(3) . ? O4 C14 1.198(3) . ? O5 C16 1.354(3) . ? O5 C4 1.438(3) . ? O6 C16 1.205(3) . ? O7 C18 1.346(4) . ? O7 C5 1.432(4) . ? O9 C18 1.180(5) . ? C1 C6 1.504(3) . ? C1 C2 1.528(3) . ? C2 C3 1.510(3) . ? C3 C4 1.509(4) . ? C4 C5 1.515(3) . ? C6 C11 1.385(3) . ? C6 C7 1.387(3) . ? C7 C8 1.389(4) . ? C8 C9 1.369(4) . ? C9 C10 1.385(4) . ? C10 C11 1.375(3) . ? C12 C13 1.482(3) . ? C14 C15 1.476(3) . ? C16 C17 1.479(3) . ? C18 C19 1.504(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 C12 O1 C1 116.28(19) . . ? C14 O3 C2 116.98(18) . . ? C16 O5 C4 117.89(19) . . ? C18 O7 C5 115.6(3) . . ? O1 C1 C6 111.2(2) . . ? O1 C1 C2 107.5(2) . . ? C6 C1 C2 112.56(18) . . ? O3 C2 C3 108.2(2) . . ? O3 C2 C1 110.43(19) . . ? C3 C2 C1 114.35(19) . . ? F2 C3 F1 105.73(17) . . ? F2 C3 C4 106.1(2) . . ? F1 C3 C4 110.1(2) . . ? F2 C3 C2 111.6(2) . . ? F1 C3 C2 106.3(2) . . ? C4 C3 C2 116.54(19) . . ? O5 C4 C3 107.10(19) . . ? O5 C4 C5 108.77(19) . . ? C3 C4 C5 112.1(2) . . ? O7 C5 C4 110.1(2) . . ? C11 C6 C7 118.6(2) . . ? C11 C6 C1 118.9(2) . . ? C7 C6 C1 122.4(2) . . ? C6 C7 C8 120.2(3) . . ? C9 C8 C7 120.4(3) . . ? C8 C9 C10 119.7(3) . . ? C11 C10 C9 120.0(3) . . ? C10 C11 C6 121.0(3) . . ? O2 C12 O1 122.7(2) . . ? O2 C12 C13 126.2(2) . . ? O1 C12 C13 111.1(2) . . ? O4 C14 O3 122.8(2) . . ? O4 C14 C15 125.77(19) . . ? O3 C14 C15 111.4(2) . . ? O6 C16 O5 122.8(2) . . ? O6 C16 C17 125.8(2) . . ? O5 C16 C17 111.4(2) . . ? O9 C18 O7 122.9(4) . . ? O9 C18 C19 126.7(4) . . ? O7 C18 C19 110.3(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.183 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.033 #==END#