  
data_181108c 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C7 H8 F N2 Na O7 S' 
_chemical_formula_weight          306.20 
  
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' 
 'N'  'N'   0.0061   0.0033 
 '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' 
 'S'  'S'   0.1246   0.1234 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Na'  'Na'   0.0362   0.0249 
 '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                    5.7233(5) 
_cell_length_b                    7.9155(7) 
_cell_length_c                    12.9158(11) 
_cell_angle_alpha                 93.5580(10) 
_cell_angle_beta                  96.119(2) 
_cell_angle_gamma                 91.6400(10) 
_cell_volume                      580.30(9) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     1171 
_cell_measurement_theta_min       2.58 
_cell_measurement_theta_max       23.887 
  
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.47 
_exptl_crystal_size_mid           0.35 
_exptl_crystal_size_min           0.18 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.752 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              312 
_exptl_absorpt_coefficient_mu     0.362 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.8481 
_exptl_absorpt_correction_T_max   0.9376 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(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             2959 
_diffrn_reflns_av_R_equivalents   0.0477 
_diffrn_reflns_av_sigmaI/netI     0.0520 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          2.58 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              2018 
_reflns_number_gt                 1488 
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1248P)²+0.0000P] where P=(Fo²+2Fc²)/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          2018 
_refine_ls_number_parameters      172 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0929 
_refine_ls_R_factor_gt            0.0782 
_refine_ls_wR_factor_ref          0.2058 
_refine_ls_wR_factor_gt           0.1947 
_refine_ls_goodness_of_fit_ref    1.106 
_refine_ls_restrained_S_all       1.106 
_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 
Na1 Na 0.7313(3) 0.8827(2) 0.44468(12) 0.0446(5) Uani 1 1 d . . . 
F1 F 0.2803(5) 0.4668(4) 0.4095(2) 0.0664(9) Uani 1 1 d . . . 
N1 N 0.1721(6) 0.5657(5) 0.2329(3) 0.0444(9) Uani 1 1 d . . . 
N2 N 0.6653(7) 0.8298(5) -0.1527(3) 0.0510(10) Uani 1 1 d . . . 
O1 O -0.0096(6) 0.6673(4) 0.3955(3) 0.0576(9) Uani 1 1 d . . . 
O2 O -0.0859(7) 0.3811(5) 0.3164(3) 0.0671(10) Uani 1 1 d . . . 
O3 O 0.4261(5) 0.7789(4) 0.3147(2) 0.0521(8) Uani 1 1 d . . . 
O4 O 0.5341(7) 0.7984(6) -0.2323(3) 0.0799(12) Uani 1 1 d . . . 
O5 O 0.8572(7) 0.8957(5) -0.1527(3) 0.0725(11) Uani 1 1 d . . . 
O6 O 1.0555(5) 1.0375(4) 0.3820(2) 0.0499(8) Uani 1 1 d . . . 
H6A H 1.0103 1.1230 0.3496 0.060 Uiso 1 1 d R . . 
H6B H 1.1349 0.9747 0.3441 0.060 Uiso 1 1 d R . . 
O7 O 0.4097(5) 0.8327(4) 0.5452(2) 0.0464(8) Uani 1 1 d . . . 
H7A H 0.4555 0.7994 0.6051 0.056 Uiso 1 1 d R . . 
H7B H 0.3072 0.7625 0.5135 0.056 Uiso 1 1 d R . . 
S1 S 0.06742(18) 0.52665(13) 0.33580(8) 0.0424(4) Uani 1 1 d . . . 
C1 C 0.3437(7) 0.6902(5) 0.2374(3) 0.0398(9) Uani 1 1 d . . . 
C2 C 0.4266(7) 0.7195(5) 0.1327(3) 0.0378(9) Uani 1 1 d . . . 
C3 C 0.2945(7) 0.6645(5) 0.0395(3) 0.0439(10) Uani 1 1 d . . . 
H3 H 0.1543 0.6026 0.0409 0.053 Uiso 1 1 calc R . . 
C4 C 0.3687(8) 0.7005(6) -0.0552(3) 0.0454(11) Uani 1 1 d . . . 
H4 H 0.2781 0.6683 -0.1178 0.055 Uiso 1 1 calc R . . 
C5 C 0.5820(7) 0.7859(5) -0.0534(3) 0.0400(9) Uani 1 1 d . . . 
C6 C 0.7204(8) 0.8378(6) 0.0376(3) 0.0454(10) Uani 1 1 d . . . 
H6 H 0.8643 0.8947 0.0360 0.055 Uiso 1 1 calc R . . 
C7 C 0.6396(7) 0.8030(6) 0.1311(3) 0.0446(10) Uani 1 1 d . . . 
H7 H 0.7300 0.8364 0.1936 0.054 Uiso 1 1 calc R . . 
  
  
_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 
Na1 O3 2.380(3) . ? 
Na1 O1 2.392(3) 1_655 ? 
Na1 O7 2.400(3) . ? 
Na1 O7 2.415(3) 2_676 ? 
Na1 O6 2.432(3) . ? 
Na1 O6 2.470(3) 2_776 ? 
Na1 Na1 3.641(3) 2_676 ? 
Na1 Na1 3.655(3) 2_776 ? 
F1 S1 1.567(3) . ? 
N1 C1 1.365(5) . ? 
N1 S1 1.560(4) . ? 
N2 O5 1.203(5) . ? 
N2 O4 1.215(5) . ? 
N2 C5 1.472(5) . ? 
O1 S1 1.422(3) . ? 
O1 Na1 2.392(3) 1_455 ? 
O2 S1 1.421(3) . ? 
O3 C1 1.228(5) . ? 
O6 Na1 2.470(3) 2_776 ? 
O6 H6A 0.8500 . ? 
O6 H6B 0.8499 . ? 
O7 Na1 2.415(3) 2_676 ? 
O7 H7A 0.8500 . ? 
O7 H7B 0.8500 . ? 
C1 C2 1.508(6) . ? 
C2 C7 1.373(6) . ? 
C2 C3 1.391(5) . ? 
C3 C4 1.380(6) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.376(6) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.379(6) . ? 
C6 C7 1.379(6) . ? 
C6 H6 0.9300 . ? 
C7 H7 0.9300 . ? 
  
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 
O3 Na1 O1 92.37(13) . 1_655 ? 
O3 Na1 O7 77.52(11) . . ? 
O1 Na1 O7 123.41(13) 1_655 . ? 
O3 Na1 O7 94.46(12) . 2_676 ? 
O1 Na1 O7 154.82(13) 1_655 2_676 ? 
O7 Na1 O7 81.75(12) . 2_676 ? 
O3 Na1 O6 115.75(12) . . ? 
O1 Na1 O6 75.73(11) 1_655 . ? 
O7 Na1 O6 157.70(12) . . ? 
O7 Na1 O6 79.47(11) 2_676 . ? 
O3 Na1 O6 160.29(13) . 2_776 ? 
O1 Na1 O6 96.48(12) 1_655 2_776 ? 
O7 Na1 O6 82.90(11) . 2_776 ? 
O7 Na1 O6 84.95(11) 2_676 2_776 ? 
O6 Na1 O6 83.57(11) . 2_776 ? 
O3 Na1 Na1 84.79(10) . 2_676 ? 
O1 Na1 Na1 164.42(12) 1_655 2_676 ? 
O7 Na1 Na1 41.02(8) . 2_676 ? 
O7 Na1 Na1 40.72(7) 2_676 2_676 ? 
O6 Na1 Na1 119.26(11) . 2_676 ? 
O6 Na1 Na1 81.96(9) 2_776 2_676 ? 
O3 Na1 Na1 157.71(11) . 2_776 ? 
O1 Na1 Na1 84.97(10) 1_655 2_776 ? 
O7 Na1 Na1 122.15(10) . 2_776 ? 
O7 Na1 Na1 79.57(9) 2_676 2_776 ? 
O6 Na1 Na1 42.18(8) . 2_776 ? 
O6 Na1 Na1 41.39(7) 2_776 2_776 ? 
Na1 Na1 Na1 103.34(8) 2_676 2_776 ? 
C1 N1 S1 118.2(3) . . ? 
O5 N2 O4 122.3(4) . . ? 
O5 N2 C5 119.7(4) . . ? 
O4 N2 C5 117.9(4) . . ? 
S1 O1 Na1 157.2(2) . 1_455 ? 
C1 O3 Na1 154.5(3) . . ? 
Na1 O6 Na1 96.43(11) . 2_776 ? 
Na1 O6 H6A 112.4 . . ? 
Na1 O6 H6A 112.6 2_776 . ? 
Na1 O6 H6B 112.4 . . ? 
Na1 O6 H6B 112.4 2_776 . ? 
H6A O6 H6B 110.1 . . ? 
Na1 O7 Na1 98.25(11) . 2_676 ? 
Na1 O7 H7A 112.2 . . ? 
Na1 O7 H7A 112.1 2_676 . ? 
Na1 O7 H7B 112.1 . . ? 
Na1 O7 H7B 112.1 2_676 . ? 
H7A O7 H7B 109.8 . . ? 
O2 S1 O1 117.8(2) . . ? 
O2 S1 N1 109.0(2) . . ? 
O1 S1 N1 116.6(2) . . ? 
O2 S1 F1 104.3(2) . . ? 
O1 S1 F1 102.28(18) . . ? 
N1 S1 F1 104.93(18) . . ? 
O3 C1 N1 127.0(4) . . ? 
O3 C1 C2 119.6(4) . . ? 
N1 C1 C2 113.4(3) . . ? 
C7 C2 C3 119.9(4) . . ? 
C7 C2 C1 118.1(3) . . ? 
C3 C2 C1 122.0(4) . . ? 
C4 C3 C2 120.8(4) . . ? 
C4 C3 H3 119.6 . . ? 
C2 C3 H3 119.6 . . ? 
C5 C4 C3 117.4(4) . . ? 
C5 C4 H4 121.3 . . ? 
C3 C4 H4 121.3 . . ? 
C4 C5 C6 123.2(4) . . ? 
C4 C5 N2 119.1(4) . . ? 
C6 C5 N2 117.7(4) . . ? 
C7 C6 C5 118.1(4) . . ? 
C7 C6 H6 120.9 . . ? 
C5 C6 H6 120.9 . . ? 
C2 C7 C6 120.5(4) . . ? 
C2 C7 H7 119.7 . . ? 
C6 C7 H7 119.7 . . ? 
  
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 
O1 Na1 O3 C1 -10.7(7) 1_655 . . . ? 
O7 Na1 O3 C1 -134.4(7) . . . . ? 
O7 Na1 O3 C1 145.1(7) 2_676 . . . ? 
O6 Na1 O3 C1 64.6(7) . . . . ? 
O6 Na1 O3 C1 -127.4(7) 2_776 . . . ? 
Na1 Na1 O3 C1 -175.3(7) 2_676 . . . ? 
Na1 Na1 O3 C1 71.8(8) 2_776 . . . ? 
O3 Na1 O6 Na1 175.93(14) . . . 2_776 ? 
O1 Na1 O6 Na1 -98.39(13) 1_655 . . 2_776 ? 
O7 Na1 O6 Na1 53.0(3) . . . 2_776 ? 
O7 Na1 O6 Na1 86.03(12) 2_676 . . 2_776 ? 
O6 Na1 O6 Na1 0.0 2_776 . . 2_776 ? 
Na1 Na1 O6 Na1 77.03(12) 2_676 . . 2_776 ? 
O3 Na1 O7 Na1 -96.47(13) . . . 2_676 ? 
O1 Na1 O7 Na1 179.00(14) 1_655 . . 2_676 ? 
O7 Na1 O7 Na1 0.0 2_676 . . 2_676 ? 
O6 Na1 O7 Na1 32.8(3) . . . 2_676 ? 
O6 Na1 O7 Na1 85.90(12) 2_776 . . 2_676 ? 
Na1 Na1 O7 Na1 72.11(13) 2_776 . . 2_676 ? 
Na1 O1 S1 O2 -51.3(6) 1_455 . . . ? 
Na1 O1 S1 N1 81.2(5) 1_455 . . . ? 
Na1 O1 S1 F1 -165.0(5) 1_455 . . . ? 
C1 N1 S1 O2 -173.1(3) . . . . ? 
C1 N1 S1 O1 50.5(4) . . . . ? 
C1 N1 S1 F1 -61.8(4) . . . . ? 
Na1 O3 C1 N1 116.1(6) . . . . ? 
Na1 O3 C1 C2 -66.4(8) . . . . ? 
S1 N1 C1 O3 -0.9(6) . . . . ? 
S1 N1 C1 C2 -178.5(3) . . . . ? 
O3 C1 C2 C7 20.8(6) . . . . ? 
N1 C1 C2 C7 -161.3(4) . . . . ? 
O3 C1 C2 C3 -159.3(4) . . . . ? 
N1 C1 C2 C3 18.6(6) . . . . ? 
C7 C2 C3 C4 -3.4(6) . . . . ? 
C1 C2 C3 C4 176.7(4) . . . . ? 
C2 C3 C4 C5 2.7(6) . . . . ? 
C3 C4 C5 C6 -0.8(7) . . . . ? 
C3 C4 C5 N2 -178.8(4) . . . . ? 
O5 N2 C5 C4 -175.7(4) . . . . ? 
O4 N2 C5 C4 4.8(6) . . . . ? 
O5 N2 C5 C6 6.2(6) . . . . ? 
O4 N2 C5 C6 -173.2(4) . . . . ? 
C4 C5 C6 C7 -0.4(7) . . . . ? 
N2 C5 C6 C7 177.6(4) . . . . ? 
C3 C2 C7 C6 2.1(7) . . . . ? 
C1 C2 C7 C6 -178.0(4) . . . . ? 
C5 C6 C7 C2 -0.2(7) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.984 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.984 
_refine_diff_density_max    0.595 
_refine_diff_density_min   -0.616 
_refine_diff_density_rms    0.145 
