data_global _publ_contact_author_email JMP29@LE.AC.UK _publ_contact_author_name 'Prof Jonathan Percy' _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_address ; Department of Chemistry University of Leicester University Road Leicester LE1 7RH UNITED KINGDOM ; _publ_section_title ; Synthesis of 4,4-Difluoroglycosides using Ring-closing Metathesis ; loop_ _publ_author_name 'Jonathan Percy' 'Christophe Audouard' 'John Fawcett' 'Gerry A Griffiths' 'Stephane Pintat' 'Clive A. Smith' data_ethyl_glycoside_29 _database_code_depnum_ccdc_archive 'CCDC 196719' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 F2 O5' _chemical_formula_weight 228.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9777(8) _cell_length_b 8.3569(10) _cell_length_c 9.3808(11) _cell_angle_alpha 82.847(2) _cell_angle_beta 71.230(2) _cell_angle_gamma 77.901(2) _cell_volume 505.45(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2609 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.38 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.145 _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 3650 _diffrn_reflns_av_R_equivalents 0.0127 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _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 1756 _reflns_number_gt 1576 _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^)+(0.0549P)^2^+0.0616P] 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 1756 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 0.82738(13) 0.40648(10) -0.00014(9) 0.0341(2) Uani 1 1 d . . . F2 F 0.88190(12) 0.26451(10) 0.19853(9) 0.0336(2) Uani 1 1 d . . . O1 O 0.45765(13) 0.34731(10) 0.35915(9) 0.0209(2) Uani 1 1 d . . . O2 O 0.26838(13) 0.14850(10) 0.46164(10) 0.0223(2) Uani 1 1 d . . . O3 O 0.46882(14) -0.03085(10) 0.19712(10) 0.0265(3) Uani 1 1 d . . . H3 H 0.4632 -0.1086 0.2635 0.040 Uiso 1 1 calc R . . O4 O 0.53835(15) 0.24104(11) 0.00009(10) 0.0264(2) Uani 1 1 d . . . H4 H 0.5025 0.1634 -0.0280 0.040 Uiso 1 1 calc R . . O5 O 0.47359(14) 0.68450(11) 0.36528(10) 0.0273(3) Uani 1 1 d . . . H5 H 0.4876 0.6907 0.4500 0.041 Uiso 1 1 calc R . . C2 C 0.36865(19) 0.22064(15) 0.32543(14) 0.0199(3) Uani 1 1 d . . . H2 H 0.2714 0.2677 0.2662 0.024 Uiso 1 1 calc R . . C3 C 0.5437(2) 0.09520(15) 0.23811(14) 0.0208(3) Uani 1 1 d . . . H3A H 0.6368 0.0473 0.3003 0.025 Uiso 1 1 calc R . . C4 C 0.6638(2) 0.17797(15) 0.09248(14) 0.0233(3) Uani 1 1 d . . . H4A H 0.7855 0.0982 0.0371 0.028 Uiso 1 1 calc R . . C5 C 0.7340(2) 0.32321(16) 0.12882(15) 0.0242(3) Uani 1 1 d . . . C6 C 0.5600(2) 0.43987(15) 0.22916(14) 0.0210(3) Uani 1 1 d . . . H6 H 0.4609 0.4935 0.1732 0.025 Uiso 1 1 calc R . . C7 C 0.0656(2) 0.23720(17) 0.53151(15) 0.0277(3) Uani 1 1 d . . . H7A H -0.0288 0.2255 0.4756 0.033 Uiso 1 1 calc R . . H7B H 0.0695 0.3552 0.5299 0.033 Uiso 1 1 calc R . . C8 C -0.0091(2) 0.16971(18) 0.69044(16) 0.0308(3) Uani 1 1 d . . . H8A H -0.0153 0.0535 0.6910 0.046 Uiso 1 1 calc R . . H8B H -0.1467 0.2302 0.7398 0.046 Uiso 1 1 calc R . . H8C H 0.0855 0.1811 0.7448 0.046 Uiso 1 1 calc R . . C9 C 0.6398(2) 0.56935(16) 0.28120(15) 0.0257(3) Uani 1 1 d . . . H9A H 0.7275 0.5167 0.3448 0.031 Uiso 1 1 calc R . . H9B H 0.7252 0.6270 0.1925 0.031 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 0.0411(5) 0.0332(5) 0.0241(4) -0.0016(3) 0.0031(4) -0.0192(4) F2 0.0265(4) 0.0356(5) 0.0412(5) -0.0055(4) -0.0132(4) -0.0047(3) O1 0.0291(5) 0.0189(5) 0.0163(5) -0.0017(4) -0.0061(4) -0.0086(4) O2 0.0229(5) 0.0213(5) 0.0198(5) 0.0000(4) -0.0025(4) -0.0048(4) O3 0.0429(6) 0.0186(5) 0.0205(5) -0.0014(4) -0.0096(4) -0.0110(4) O4 0.0417(6) 0.0221(5) 0.0194(5) -0.0010(4) -0.0117(4) -0.0106(4) O5 0.0429(6) 0.0211(5) 0.0206(5) -0.0028(4) -0.0126(4) -0.0065(4) C2 0.0248(7) 0.0194(6) 0.0173(6) -0.0008(5) -0.0068(5) -0.0073(5) C3 0.0265(7) 0.0179(6) 0.0196(6) -0.0027(5) -0.0083(5) -0.0048(5) C4 0.0275(7) 0.0211(7) 0.0191(7) -0.0032(5) -0.0038(5) -0.0037(5) C5 0.0262(7) 0.0260(7) 0.0202(6) 0.0011(5) -0.0051(5) -0.0090(5) C6 0.0276(7) 0.0194(6) 0.0169(6) 0.0016(5) -0.0065(5) -0.0081(5) C7 0.0221(7) 0.0309(8) 0.0268(7) -0.0035(6) -0.0045(6) -0.0014(5) C8 0.0248(7) 0.0361(8) 0.0272(7) -0.0032(6) -0.0018(6) -0.0050(6) C9 0.0335(7) 0.0232(7) 0.0235(7) -0.0014(5) -0.0097(6) -0.0102(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 C5 1.3585(15) . ? F2 C5 1.3695(15) . ? O1 C6 1.4255(14) . ? O1 C2 1.4464(15) . ? O2 C2 1.3767(15) . ? O2 C7 1.4373(15) . ? O3 C3 1.4110(15) . ? O4 C4 1.4059(15) . ? O5 C9 1.4233(16) . ? C2 C3 1.5148(17) . ? C3 C4 1.5227(17) . ? C4 C5 1.5128(19) . ? C5 C6 1.5189(18) . ? C6 C9 1.5092(17) . ? C7 C8 1.4921(19) . ? 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 C6 O1 C2 113.88(9) . . ? C2 O2 C7 113.53(9) . . ? O2 C2 O1 106.73(9) . . ? O2 C2 C3 109.27(10) . . ? O1 C2 C3 107.66(10) . . ? O3 C3 C2 111.14(10) . . ? O3 C3 C4 107.05(10) . . ? C2 C3 C4 109.25(10) . . ? O4 C4 C5 106.23(10) . . ? O4 C4 C3 110.99(10) . . ? C5 C4 C3 109.48(10) . . ? F1 C5 F2 105.92(10) . . ? F1 C5 C4 110.39(11) . . ? F2 C5 C4 107.97(10) . . ? F1 C5 C6 109.55(10) . . ? F2 C5 C6 109.68(11) . . ? C4 C5 C6 113.06(11) . . ? O1 C6 C9 108.10(10) . . ? O1 C6 C5 108.20(9) . . ? C9 C6 C5 111.53(11) . . ? O2 C7 C8 108.66(10) . . ? O5 C9 C6 110.54(10) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.184 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.062