# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'J Percy' 'Timo Anderl' 'Christophe Audouard' 'Afjal Miah' 'Giuseppe Rinaudo' 'Kuldip Singh' _publ_contact_author_name J.M.Percy _publ_contact_author_email JONATHAN.PERCY@STRATH.AC.UK _publ_section_title ; Syntheses of Difluorinated Carbasugar Phosphates from Trifluoroethanol ; # Attachment '9.cif' data_9 _database_code_depnum_ccdc_archive 'CCDC 740066' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H16 F2 O2' _chemical_formula_sum 'C14 H16 F2 O2' _chemical_formula_weight 254.27 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 6.367(2) _cell_length_b 8.922(3) _cell_length_c 12.227(4) _cell_angle_alpha 69.010(5) _cell_angle_beta 80.262(5) _cell_angle_gamma 75.241(5) _cell_volume 624.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 733 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 23.16 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max .25 _exptl_crystal_size_mid .11 _exptl_crystal_size_min .04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.109 _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 Apex 2000 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 3827 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 23.31 _reflns_number_total 1786 _reflns_number_gt 1463 _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^)+(0.0288P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1786 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0783 _refine_ls_wR_factor_gt 0.0743 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 0.19899(15) 0.25970(13) 0.38781(8) 0.0457(3) Uani 1 1 d . . . F2 F 0.29874(16) 0.47234(13) 0.39450(9) 0.0449(3) Uani 1 1 d . . . O2 O 0.37567(16) 0.67647(13) 0.02949(10) 0.0299(3) Uani 1 1 d . . . O1 O 0.27621(17) 0.36441(14) 0.14317(10) 0.0328(3) Uani 1 1 d . . . H1 H 0.3914 0.3660 0.0981 0.049 Uiso 1 1 calc R . . C2 C 0.4005(3) 0.5968(2) 0.15253(15) 0.0283(4) Uani 1 1 d . . . H2 H 0.3545 0.6818 0.1923 0.034 Uiso 1 1 calc R . . C1 C 0.2622(3) 0.4681(2) 0.20896(15) 0.0274(4) Uani 1 1 d . . . H1A H 0.1065 0.5255 0.2175 0.033 Uiso 1 1 calc R . . C7 C 0.3352(3) 0.3663(2) 0.33060(15) 0.0316(4) Uani 1 1 d . . . C5 C 0.5683(3) 0.2750(2) 0.33249(15) 0.0306(4) Uani 1 1 d . . . H5 H 0.5774 0.1802 0.3052 0.037 Uiso 1 1 calc R . . C4 C 0.7093(3) 0.3825(2) 0.24603(15) 0.0304(4) Uani 1 1 d . . . H4 H 0.8626 0.3462 0.2494 0.037 Uiso 1 1 calc R . . C3 C 0.6373(3) 0.5239(2) 0.16549(15) 0.0293(4) Uani 1 1 d . . . H3 H 0.7407 0.5818 0.1134 0.035 Uiso 1 1 calc R . . C8 C 0.1557(2) 0.7611(2) 0.00412(15) 0.0300(4) Uani 1 1 d . . . H8A H 0.0811 0.8005 0.0697 0.036 Uiso 1 1 calc R . . H8B H 0.0750 0.6846 -0.0036 0.036 Uiso 1 1 calc R . . C9 C 0.1554(3) 0.9033(2) -0.10704(15) 0.0263(4) Uani 1 1 d . . . C10 C 0.3119(3) 0.9978(2) -0.13840(16) 0.0306(4) Uani 1 1 d . . . H10 H 0.4268 0.9697 -0.0895 0.037 Uiso 1 1 calc R . . C11 C 0.3032(3) 1.1319(2) -0.23942(16) 0.0376(5) Uani 1 1 d . . . H11 H 0.4125 1.1948 -0.2600 0.045 Uiso 1 1 calc R . . C12 C 0.1363(3) 1.1757(2) -0.31134(16) 0.0412(5) Uani 1 1 d . . . H12 H 0.1299 1.2689 -0.3808 0.049 Uiso 1 1 calc R . . C13 C -0.0200(3) 1.0831(2) -0.28130(16) 0.0384(5) Uani 1 1 d . . . H13 H -0.1349 1.1123 -0.3304 0.046 Uiso 1 1 calc R . . C14 C -0.0113(3) 0.9476(2) -0.18017(15) 0.0319(5) Uani 1 1 d . . . H14 H -0.1200 0.8842 -0.1604 0.038 Uiso 1 1 calc R . . C6 C 0.6488(3) 0.2043(2) 0.45529(16) 0.0441(5) Uani 1 1 d . . . H6A H 0.6528 0.2943 0.4825 0.066 Uiso 1 1 calc R . . H6B H 0.7956 0.1359 0.4526 0.066 Uiso 1 1 calc R . . H6C H 0.5498 0.1374 0.5095 0.066 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 0.0348(6) 0.0547(7) 0.0352(7) 0.0026(5) -0.0009(5) -0.0150(5) F2 0.0458(7) 0.0546(7) 0.0319(7) -0.0204(6) -0.0054(5) 0.0039(5) O2 0.0231(7) 0.0324(7) 0.0277(7) -0.0062(6) -0.0029(5) 0.0004(5) O1 0.0288(7) 0.0385(8) 0.0339(8) -0.0125(6) -0.0007(5) -0.0124(6) C2 0.0279(10) 0.0297(10) 0.0260(10) -0.0095(8) -0.0030(8) -0.0030(8) C1 0.0225(9) 0.0325(10) 0.0259(10) -0.0099(8) -0.0028(7) -0.0026(8) C7 0.0326(11) 0.0363(11) 0.0255(10) -0.0090(9) 0.0008(8) -0.0102(9) C5 0.0279(10) 0.0322(10) 0.0298(11) -0.0089(8) -0.0058(8) -0.0028(8) C4 0.0242(10) 0.0360(11) 0.0345(11) -0.0157(10) -0.0064(8) -0.0037(8) C3 0.0247(10) 0.0334(11) 0.0333(11) -0.0126(9) -0.0019(8) -0.0100(8) C8 0.0222(10) 0.0306(10) 0.0332(11) -0.0086(9) -0.0018(8) -0.0016(8) C9 0.0251(10) 0.0239(10) 0.0288(10) -0.0105(8) -0.0007(8) -0.0015(8) C10 0.0274(10) 0.0312(11) 0.0346(11) -0.0141(9) -0.0032(8) -0.0034(8) C11 0.0404(12) 0.0309(11) 0.0404(12) -0.0121(10) 0.0063(9) -0.0117(9) C12 0.0488(13) 0.0346(11) 0.0289(12) -0.0055(9) 0.0009(9) 0.0004(10) C13 0.0381(12) 0.0430(13) 0.0316(12) -0.0134(10) -0.0121(9) 0.0033(10) C14 0.0264(10) 0.0351(11) 0.0373(12) -0.0169(10) -0.0043(8) -0.0035(8) C6 0.0395(12) 0.0515(13) 0.0334(12) -0.0072(10) -0.0096(9) -0.0016(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 F1 C7 1.3730(19) . ? F2 C7 1.384(2) . ? O2 C2 1.4320(19) . ? O2 C8 1.4385(18) . ? O1 C1 1.4062(19) . ? O1 H1 0.8400 . ? C2 C3 1.493(2) . ? C2 C1 1.521(2) . ? C2 H2 1.0000 . ? C1 C7 1.518(2) . ? C1 H1A 1.0000 . ? C7 C5 1.500(2) . ? C5 C4 1.495(2) . ? C5 C6 1.527(2) . ? C5 H5 1.0000 . ? C4 C3 1.319(2) . ? C4 H4 0.9500 . ? C3 H3 0.9500 . ? C8 C9 1.490(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.385(2) . ? C9 C14 1.391(2) . ? C10 C11 1.375(3) . ? C10 H10 0.9500 . ? C11 C12 1.383(2) . ? C11 H11 0.9500 . ? C12 C13 1.374(2) . ? C12 H12 0.9500 . ? C13 C14 1.382(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 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 C2 O2 C8 113.45(12) . . ? C1 O1 H1 109.5 . . ? O2 C2 C3 107.33(13) . . ? O2 C2 C1 112.33(13) . . ? C3 C2 C1 111.70(14) . . ? O2 C2 H2 108.5 . . ? C3 C2 H2 108.5 . . ? C1 C2 H2 108.5 . . ? O1 C1 C7 109.64(14) . . ? O1 C1 C2 113.21(14) . . ? C7 C1 C2 108.25(13) . . ? O1 C1 H1A 108.5 . . ? C7 C1 H1A 108.5 . . ? C2 C1 H1A 108.5 . . ? F1 C7 F2 104.51(13) . . ? F1 C7 C5 110.34(15) . . ? F2 C7 C5 110.19(13) . . ? F1 C7 C1 109.36(14) . . ? F2 C7 C1 107.00(14) . . ? C5 C7 C1 114.89(14) . . ? C4 C5 C7 109.75(14) . . ? C4 C5 C6 112.12(14) . . ? C7 C5 C6 113.14(14) . . ? C4 C5 H5 107.2 . . ? C7 C5 H5 107.2 . . ? C6 C5 H5 107.2 . . ? C3 C4 C5 125.04(16) . . ? C3 C4 H4 117.5 . . ? C5 C4 H4 117.5 . . ? C4 C3 C2 122.93(16) . . ? C4 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? O2 C8 C9 110.27(13) . . ? O2 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? O2 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C14 118.36(16) . . ? C10 C9 C8 122.10(15) . . ? C14 C9 C8 119.50(15) . . ? C11 C10 C9 120.84(16) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 120.48(17) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 119.29(18) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 120.47(17) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C9 120.56(17) . . ? C13 C14 H14 119.7 . . ? C9 C14 H14 119.7 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 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 C8 O2 C2 C3 -176.56(13) . . . . ? C8 O2 C2 C1 60.28(17) . . . . ? O2 C2 C1 O1 46.13(18) . . . . ? C3 C2 C1 O1 -74.55(17) . . . . ? O2 C2 C1 C7 167.90(13) . . . . ? C3 C2 C1 C7 47.23(18) . . . . ? O1 C1 C7 F1 -61.88(17) . . . . ? C2 C1 C7 F1 174.18(13) . . . . ? O1 C1 C7 F2 -174.53(12) . . . . ? C2 C1 C7 F2 61.53(17) . . . . ? O1 C1 C7 C5 62.81(19) . . . . ? C2 C1 C7 C5 -61.13(19) . . . . ? F1 C7 C5 C4 165.96(13) . . . . ? F2 C7 C5 C4 -79.14(17) . . . . ? C1 C7 C5 C4 41.8(2) . . . . ? F1 C7 C5 C6 -67.99(19) . . . . ? F2 C7 C5 C6 46.9(2) . . . . ? C1 C7 C5 C6 167.84(15) . . . . ? C7 C5 C4 C3 -11.4(2) . . . . ? C6 C5 C4 C3 -138.08(18) . . . . ? C5 C4 C3 C2 1.4(3) . . . . ? O2 C2 C3 C4 -143.96(16) . . . . ? C1 C2 C3 C4 -20.4(2) . . . . ? C2 O2 C8 C9 151.11(13) . . . . ? O2 C8 C9 C10 -36.4(2) . . . . ? O2 C8 C9 C14 146.16(15) . . . . ? C14 C9 C10 C11 -0.1(2) . . . . ? C8 C9 C10 C11 -177.65(16) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C11 C12 C13 C14 0.1(3) . . . . ? C12 C13 C14 C9 0.2(3) . . . . ? C10 C9 C14 C13 -0.2(2) . . . . ? C8 C9 C14 C13 177.35(15) . . . . ? 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 O1 H1 O2 0.84 2.03 2.8390(17) 160.8 2_665 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.154 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.032