# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Gunter Haufe' 'Jan Balzarini' 'De Clercq,Erik' 'Thomas C. Rosen' _publ_contact_author_name 'Prof Gunter Haufe' _publ_contact_author_address ; Organisch-Chemisches Institut Universitat Munster Corrensstr. 40 M=FCnster D-48149 GERMANY ; _publ_contact_author_email HAUFE@UNI-MUENSTER.DE _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthesis and antiviral activity of monofluorinated cyclopropanoid nucleosides ; data_haf1822 _database_code_CSD 218773 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H9 F O4' _chemical_formula_weight 176.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.120(1) _cell_length_b 7.299(1) _cell_length_c 10.965(1) _cell_angle_alpha 90.00 _cell_angle_beta 98.76(1) _cell_angle_gamma 90.00 _cell_volume 800.49(15) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 40.12 _cell_measurement_theta_max 46.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 1.174 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5914 _exptl_absorpt_correction_T_max 0.6510 _exptl_absorpt_process_details 'based on \y scan data' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method '\w/2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1.5 _diffrn_reflns_number 1726 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 5.54 _diffrn_reflns_theta_max 74.45 _reflns_number_total 1633 _reflns_number_gt 1573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Express (Nonius B.V., 1994)' _computing_cell_refinement 'Express (Nonius B.V., 1994)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1120P)^2^+0.3017P] 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 'refined as riding atoms' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1633 _refine_ls_number_parameters 112 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1582 _refine_ls_wR_factor_gt 0.1559 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.58629(16) 0.3180(2) 0.91669(14) 0.0315(4) Uani 1 1 d . . . C2 C 0.65050(15) 0.1747(2) 0.84954(15) 0.0321(4) Uani 1 1 d . . . C3 C 0.59915(18) -0.0172(2) 0.84031(16) 0.0379(4) Uani 1 1 d . . . H3A H 0.5199 -0.0451 0.8784 0.046 Uiso 1 1 calc R . . H3B H 0.6648 -0.1166 0.8443 0.046 Uiso 1 1 calc R . . C4 C 0.58090(17) 0.1028(2) 0.72737(14) 0.0345(4) Uani 1 1 d . . . H4 H 0.6405 0.0743 0.6662 0.041 Uiso 1 1 calc R . . C5 C 0.44471(17) 0.1701(2) 0.67387(16) 0.0373(4) Uani 1 1 d . . . H5A H 0.4112 0.1030 0.5980 0.045 Uiso 1 1 calc R . . H5B H 0.3821 0.1525 0.7328 0.045 Uiso 1 1 calc R . . O5 O 0.45782(11) 0.36292(17) 0.64759(11) 0.0372(4) Uani 1 1 d . . . C6 C 0.34471(16) 0.4614(2) 0.63398(14) 0.0345(4) Uani 1 1 d . . . O6 O 0.23619(13) 0.3952(2) 0.63844(13) 0.0482(4) Uani 1 1 d . . . C7 C 0.3713(2) 0.6590(3) 0.6130(2) 0.0490(5) Uani 1 1 d . . . H7A H 0.2918 0.7300 0.6199 0.073 Uiso 1 1 calc R . . H7B H 0.3950 0.6747 0.5312 0.073 Uiso 1 1 calc R . . H7C H 0.4445 0.7007 0.6743 0.073 Uiso 1 1 calc R . . F F 0.78597(10) 0.19771(16) 0.85787(10) 0.0430(4) Uani 1 1 d . . . O11 O 0.47103(12) 0.29967(17) 0.93582(12) 0.0387(4) Uani 1 1 d . . . O12 O 0.66118(12) 0.46007(17) 0.94932(12) 0.0397(4) Uani 1 1 d . . . H12 H 0.6182 0.5359 0.9838 0.060 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 C1 0.0291(8) 0.0321(8) 0.0347(8) 0.0015(6) 0.0092(6) -0.0006(6) C2 0.0261(8) 0.0334(8) 0.0385(8) 0.0025(6) 0.0104(6) 0.0024(6) C3 0.0434(9) 0.0295(8) 0.0429(9) 0.0024(6) 0.0131(7) 0.0053(7) C4 0.0361(9) 0.0338(8) 0.0354(8) -0.0008(6) 0.0113(6) 0.0044(6) C5 0.0350(9) 0.0362(9) 0.0409(9) -0.0014(7) 0.0060(7) -0.0012(7) O5 0.0301(7) 0.0376(7) 0.0453(7) 0.0051(5) 0.0100(5) 0.0039(5) C6 0.0303(8) 0.0414(9) 0.0327(8) -0.0008(6) 0.0077(6) 0.0049(6) O6 0.0306(7) 0.0518(8) 0.0635(8) 0.0034(6) 0.0110(6) 0.0030(5) C7 0.0433(10) 0.0428(11) 0.0630(11) 0.0063(9) 0.0154(9) 0.0074(8) F 0.0258(6) 0.0508(7) 0.0539(7) 0.0002(4) 0.0112(4) 0.0048(4) O11 0.0326(7) 0.0379(7) 0.0494(7) -0.0088(5) 0.0186(5) -0.0054(5) O12 0.0326(7) 0.0353(7) 0.0542(8) -0.0077(5) 0.0163(5) -0.0054(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 O11 1.2235(19) . ? C1 O12 1.302(2) . ? C1 C2 1.485(2) . ? C2 F 1.3704(18) . ? C2 C3 1.492(2) . ? C2 C4 1.509(2) . ? C3 C4 1.505(2) . ? C4 C5 1.496(2) . ? C5 O5 1.447(2) . ? O5 C6 1.340(2) . ? C6 O6 1.207(2) . ? C6 C7 1.492(3) . ? 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 O11 C1 O12 124.75(15) . . ? O11 C1 C2 120.59(15) . . ? O12 C1 C2 114.65(14) . . ? F C2 C1 112.92(14) . . ? F C2 C3 117.03(14) . . ? C1 C2 C3 121.38(14) . . ? F C2 C4 115.39(13) . . ? C1 C2 C4 120.31(14) . . ? C3 C2 C4 60.19(11) . . ? C2 C3 C4 60.49(11) . . ? C5 C4 C3 120.27(15) . . ? C5 C4 C2 120.74(14) . . ? C3 C4 C2 59.32(11) . . ? O5 C5 C4 106.90(13) . . ? C6 O5 C5 116.16(13) . . ? O6 C6 O5 123.22(17) . . ? O6 C6 C7 125.42(16) . . ? O5 C6 C7 111.36(15) . . ? 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 O11 C1 C2 F -167.47(14) . . . . ? O12 C1 C2 F 13.8(2) . . . . ? O11 C1 C2 C3 -20.8(2) . . . . ? O12 C1 C2 C3 160.49(15) . . . . ? O11 C1 C2 C4 50.7(2) . . . . ? O12 C1 C2 C4 -128.05(16) . . . . ? F C2 C3 C4 -105.21(15) . . . . ? C1 C2 C3 C4 109.38(17) . . . . ? C2 C3 C4 C5 -110.00(16) . . . . ? F C2 C4 C5 -142.86(15) . . . . ? C1 C2 C4 C5 -1.9(2) . . . . ? C3 C2 C4 C5 109.21(17) . . . . ? F C2 C4 C3 107.93(16) . . . . ? C1 C2 C4 C3 -111.12(16) . . . . ? C3 C4 C5 O5 134.57(15) . . . . ? C2 C4 C5 O5 64.46(19) . . . . ? C4 C5 O5 C6 -160.90(13) . . . . ? C5 O5 C6 O6 -2.6(2) . . . . ? C5 O5 C6 C7 177.40(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 74.45 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.319 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.088