data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'J M Percy' _publ_contact_author_name 'Jonathan Percy' _publ_contact_author_email JONATHAN.PERCY@STRATH.AC.UK _publ_section_title ; Developing an Asymmetric, Stereodivergent Route to Selected 6-Deoxy-6-fluoro-hexoses ; # Attachment '6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 700908' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H9 F O2' _chemical_formula_sum 'C7 H9 F O2' _chemical_formula_weight 144.14 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 8.4625(16) _cell_length_b 8.0276(16) _cell_length_c 21.142(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.378(5) _cell_angle_gamma 90.00 _cell_volume 1436.2(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 889 _cell_measurement_theta_min 3.498 _cell_measurement_theta_max 21.554 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.113 _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 ' Bruker 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 4948 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1256 _reflns_number_gt 1114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0491P)^2^+0.6068P] 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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1256 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.004 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 -0.36502(13) 0.23548(14) 0.70030(6) 0.0486(4) Uani 1 1 d . . . O1 O 0.41342(14) 0.18293(15) 0.54905(6) 0.0315(4) Uani 1 1 d . . . O2 O 0.40169(15) 0.43658(16) 0.59260(7) 0.0435(4) Uani 1 1 d . . . C1 C 0.3408(2) 0.3036(2) 0.58140(8) 0.0277(4) Uani 1 1 d . . . C2 C 0.1815(2) 0.2528(2) 0.60121(8) 0.0277(4) Uani 1 1 d . . . H2 H 0.1439 0.1449 0.5906 0.033 Uiso 1 1 calc R . . C3 C 0.0896(2) 0.3557(2) 0.63375(8) 0.0277(4) Uani 1 1 d . . . H3 H 0.1304 0.4631 0.6432 0.033 Uiso 1 1 calc R . . C4 C -0.0677(2) 0.3174(2) 0.65595(8) 0.0275(4) Uani 1 1 d . . . H4 H -0.1115 0.2112 0.6466 0.033 Uiso 1 1 calc R . . C5 C -0.1532(2) 0.4252(2) 0.68898(8) 0.0298(4) Uani 1 1 d . . . H5 H -0.1069 0.5308 0.6973 0.036 Uiso 1 1 calc R . . C6 C -0.3140(2) 0.3960(2) 0.71411(9) 0.0331(5) Uani 1 1 d . . . H6A H -0.3131 0.4127 0.7605 0.040 Uiso 1 1 calc R . . H6B H -0.3883 0.4776 0.6953 0.040 Uiso 1 1 calc R . . C7 C 0.5722(2) 0.2204(2) 0.52886(9) 0.0355(5) Uani 1 1 d . . . H7A H 0.5709 0.3199 0.5020 0.053 Uiso 1 1 calc R . . H7B H 0.6142 0.1260 0.5048 0.053 Uiso 1 1 calc R . . H7C H 0.6394 0.2406 0.5660 0.053 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 0.0425(7) 0.0409(7) 0.0627(8) -0.0052(6) 0.0197(6) -0.0135(5) O1 0.0256(7) 0.0301(7) 0.0389(7) -0.0041(5) 0.0079(5) -0.0029(5) O2 0.0302(8) 0.0326(8) 0.0678(10) -0.0133(7) 0.0102(7) -0.0076(6) C1 0.0260(9) 0.0249(9) 0.0322(10) 0.0011(8) -0.0004(7) -0.0007(8) C2 0.0260(9) 0.0258(9) 0.0314(9) 0.0002(8) -0.0008(7) -0.0031(8) C3 0.0256(9) 0.0274(9) 0.0299(9) 0.0006(8) -0.0015(7) -0.0032(7) C4 0.0259(9) 0.0259(9) 0.0307(10) 0.0012(7) -0.0001(7) -0.0030(8) C5 0.0285(10) 0.0280(10) 0.0329(10) 0.0010(8) 0.0001(8) -0.0023(8) C6 0.0316(10) 0.0326(10) 0.0351(10) -0.0001(8) 0.0056(8) -0.0016(8) C7 0.0223(9) 0.0421(12) 0.0421(11) -0.0012(9) 0.0072(8) -0.0011(8) _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 C6 1.390(2) . ? O1 C1 1.338(2) . ? O1 C7 1.444(2) . ? O2 C1 1.208(2) . ? C1 C2 1.472(2) . ? C2 C3 1.330(2) . ? C2 H2 0.9500 . ? C3 C4 1.447(2) . ? C3 H3 0.9500 . ? C4 C5 1.329(2) . ? C4 H4 0.9500 . ? C5 C6 1.483(2) . ? C5 H5 0.9500 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? 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 C1 O1 C7 115.57(14) . . ? O2 C1 O1 122.93(17) . . ? O2 C1 C2 125.40(17) . . ? O1 C1 C2 111.67(15) . . ? C3 C2 C1 121.04(16) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 125.37(17) . . ? C2 C3 H3 117.3 . . ? C4 C3 H3 117.3 . . ? C5 C4 C3 122.49(17) . . ? C5 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? C4 C5 C6 126.13(17) . . ? C4 C5 H5 116.9 . . ? C6 C5 H5 116.9 . . ? F1 C6 C5 110.85(15) . . ? F1 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? F1 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 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 C7 O1 C1 O2 1.0(3) . . . . ? C7 O1 C1 C2 -178.66(14) . . . . ? O2 C1 C2 C3 0.7(3) . . . . ? O1 C1 C2 C3 -179.70(16) . . . . ? C1 C2 C3 C4 -179.34(16) . . . . ? C2 C3 C4 C5 179.18(17) . . . . ? C3 C4 C5 C6 -179.31(17) . . . . ? C4 C5 C6 F1 1.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.223 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.038