data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H19 F3 N2 O5 S'
_chemical_formula_weight          384.37
 
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'
 
_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                    7.2689(15)
_cell_length_b                    7.8204(16)
_cell_length_c                    15.025(3)
_cell_angle_alpha                 103.85(3)
_cell_angle_beta                  99.40(3)
_cell_angle_gamma                 92.57(3)
_cell_volume                      815.0(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     4127
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.566
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              400
_exptl_absorpt_coefficient_mu     0.260
_exptl_absorpt_correction_type    multi-scans
_exptl_absorpt_correction_T_min   0.9694
_exptl_absorpt_correction_T_max   0.9897
_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          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        '\\f and \\w scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             7049
_diffrn_reflns_av_R_equivalents   0.0772
_diffrn_reflns_av_sigmaI/netI     0.1342
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.38
_reflns_number_total              3230
_reflns_number_gt                 1782
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, Pearce 1995)'
_computing_publication_material   ?
 
_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)+(0.0676P)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      SHELXL
_refine_ls_extinction_coef        0.001(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3230
_refine_ls_number_parameters      232
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1347
_refine_ls_R_factor_gt            0.0613
_refine_ls_wR_factor_ref          0.1594
_refine_ls_wR_factor_gt           0.1305
_refine_ls_goodness_of_fit_ref    0.960
_refine_ls_restrained_S_all       0.960
_refine_ls_shift/su_max           0.003
_refine_ls_shift/su_mean          0.001
 
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
C14 C 0.6629(6) 0.4193(5) 0.3845(3) 0.0339(9) Uani 1 1 d . . .
O3 O 0.6112(4) 0.4829(4) 0.22310(19) 0.0463(8) Uani 1 1 d . . .
O4 O 0.7678(4) 0.7144(3) 0.3546(2) 0.0446(8) Uani 1 1 d . . .
O5 O 0.9286(4) 0.4582(4) 0.2978(2) 0.0489(8) Uani 1 1 d . . .
F1 F 0.6481(4) 0.2454(3) 0.35258(18) 0.0580(8) Uani 1 1 d . . .
F2 F 0.4938(3) 0.4656(4) 0.39672(19) 0.0645(8) Uani 1 1 d . . .
F3 F 0.7740(3) 0.4562(3) 0.46747(16) 0.0542(7) Uani 1 1 d . . .
S1 S 0.75336(13) 0.53149(12) 0.30550(7) 0.0304(3) Uani 1 1 d . . .
C1 C 0.2140(5) -0.4819(4) 0.0560(3) 0.0276(9) Uani 1 1 d . . .
C2 C 0.3075(5) -0.4010(5) -0.0050(3) 0.0273(9) Uani 1 1 d . . .
H2 H 0.3200 -0.4704 -0.0645 0.033 Uiso 1 1 calc R . .
C3 C 0.3744(5) -0.2343(4) 0.0210(2) 0.0261(9) Uani 1 1 d . . .
H3 H 0.4388 -0.1912 -0.0205 0.031 Uiso 1 1 calc R . .
C4 C 0.3577(5) -0.1066(4) 0.1106(3) 0.0240(8) Uani 1 1 d . . .
C5 C 0.6952(5) -0.0540(5) 0.1631(3) 0.0360(10) Uani 1 1 d . . .
H5A H 0.7041 -0.0876 0.2223 0.054 Uiso 1 1 calc R . .
H5B H 0.7984 0.0343 0.1675 0.054 Uiso 1 1 calc R . .
H5C H 0.7025 -0.1587 0.1131 0.054 Uiso 1 1 calc R . .
C6 C 0.3245(5) -0.2009(4) 0.1854(2) 0.0232(8) Uani 1 1 d . . .
H6 H 0.4455 -0.2456 0.2084 0.028 Uiso 1 1 calc R . .
C7 C 0.1781(5) -0.3623(4) 0.1447(2) 0.0277(9) Uani 1 1 d . . .
H7A H 0.1767 -0.4317 0.1918 0.033 Uiso 1 1 calc R . .
H7B H 0.0526 -0.3193 0.1328 0.033 Uiso 1 1 calc R . .
C8 C 0.1990(5) 0.0076(4) 0.0932(2) 0.0241(8) Uani 1 1 d . . .
H8A H 0.0789 -0.0672 0.0723 0.029 Uiso 1 1 calc R . .
H8B H 0.2190 0.0658 0.0434 0.029 Uiso 1 1 calc R . .
C9 C 0.1903(5) 0.1471(4) 0.1820(2) 0.0258(9) Uani 1 1 d . . .
H9A H 0.3000 0.2350 0.1960 0.031 Uiso 1 1 calc R . .
H9B H 0.0761 0.2096 0.1725 0.031 Uiso 1 1 calc R . .
C10 C 0.1883(5) 0.0674(4) 0.2633(2) 0.0231(8) Uani 1 1 d . . .
C11 C 0.0995(5) 0.0943(5) 0.4158(3) 0.0324(9) Uani 1 1 d . . .
H11A H -0.0165 0.0158 0.4062 0.039 Uiso 1 1 calc R . .
H11B H 0.0976 0.1966 0.4692 0.039 Uiso 1 1 calc R . .
C12 C 0.2678(5) -0.0041(5) 0.4353(3) 0.0343(10) Uani 1 1 d . . .
H12A H 0.2585 -0.0551 0.4888 0.041 Uiso 1 1 calc R . .
H12B H 0.3823 0.0786 0.4518 0.041 Uiso 1 1 calc R . .
C13 C 0.2813(5) -0.1504(5) 0.3509(2) 0.0296(9) Uani 1 1 d . . .
H13A H 0.4025 -0.2019 0.3611 0.036 Uiso 1 1 calc R . .
H13B H 0.1799 -0.2450 0.3418 0.036 Uiso 1 1 calc R . .
N1 N 0.2659(4) -0.0818(4) 0.2661(2) 0.0237(7) Uani 1 1 d . . .
N2 N 0.1113(4) 0.1549(4) 0.3318(2) 0.0286(8) Uani 1 1 d . . .
O1 O 0.1541(3) -0.6382(3) 0.03313(18) 0.0340(7) Uani 1 1 d . . .
O2 O 0.5213(3) 0.0186(3) 0.14325(17) 0.0292(6) Uani 1 1 d . . .
H2A H 0.062(4) 0.250(4) 0.323(2) 0.003(8) Uiso 1 1 d . . .
 
 
_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
C14 F1 1.322(4) . ?
C14 F2 1.325(4) . ?
C14 F3 1.329(4) . ?
C14 S1 1.820(4) . ?
O3 S1 1.438(3) . ?
O4 S1 1.434(3) . ?
O5 S1 1.431(3) . ?
C1 O1 1.226(4) . ?
C1 C2 1.464(5) . ?
C1 C7 1.503(5) . ?
C2 C3 1.314(5) . ?
C3 C4 1.499(5) . ?
C4 O2 1.445(4) . ?
C4 C8 1.517(5) . ?
C4 C6 1.529(4) . ?
C5 O2 1.425(4) . ?
C6 N1 1.478(4) . ?
C6 C7 1.548(5) . ?
C8 C9 1.520(5) . ?
C9 C10 1.499(4) . ?
C10 N2 1.314(4) . ?
C10 N1 1.326(4) . ?
C11 N2 1.464(5) . ?
C11 C12 1.500(5) . ?
C12 C13 1.510(5) . ?
C13 N1 1.485(4) . ?
 
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
F1 C14 F2 107.0(3) . . ?
F1 C14 F3 106.6(3) . . ?
F2 C14 F3 108.3(3) . . ?
F1 C14 S1 112.0(3) . . ?
F2 C14 S1 111.0(3) . . ?
F3 C14 S1 111.6(3) . . ?
O5 S1 O4 114.83(19) . . ?
O5 S1 O3 116.02(19) . . ?
O4 S1 O3 114.65(18) . . ?
O5 S1 C14 102.45(17) . . ?
O4 S1 C14 103.15(17) . . ?
O3 S1 C14 103.11(18) . . ?
O1 C1 C2 121.9(3) . . ?
O1 C1 C7 120.5(3) . . ?
C2 C1 C7 117.4(3) . . ?
C3 C2 C1 121.4(3) . . ?
C2 C3 C4 125.4(3) . . ?
O2 C4 C3 110.6(3) . . ?
O2 C4 C8 103.8(2) . . ?
C3 C4 C8 109.6(3) . . ?
O2 C4 C6 110.8(3) . . ?
C3 C4 C6 112.0(3) . . ?
C8 C4 C6 109.8(3) . . ?
N1 C6 C4 112.5(3) . . ?
N1 C6 C7 109.7(3) . . ?
C4 C6 C7 111.2(3) . . ?
C1 C7 C6 113.9(3) . . ?
C4 C8 C9 110.0(3) . . ?
C10 C9 C8 111.7(3) . . ?
N2 C10 N1 122.2(3) . . ?
N2 C10 C9 116.9(3) . . ?
N1 C10 C9 120.9(3) . . ?
N2 C11 C12 107.7(3) . . ?
C11 C12 C13 110.4(3) . . ?
N1 C13 C12 110.7(3) . . ?
C10 N1 C6 124.2(3) . . ?
C10 N1 C13 120.7(3) . . ?
C6 N1 C13 114.8(3) . . ?
C10 N2 C11 123.2(3) . . ?
C5 O2 C4 116.1(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.872
_diffrn_reflns_theta_full              27.38
_diffrn_measured_fraction_theta_full   0.872
_refine_diff_density_max    0.399
_refine_diff_density_min   -0.382
_refine_diff_density_rms    0.082
