 
data_global 
_audit_creation_date                               2016-02-03
_audit_creation_method            SHELXL-2014

data_I
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety         'C13 H14 N O2, C F3 O3 S'
_chemical_formula_sum            'C14 H14 F3 N O5 S' 
_chemical_formula_weight          365.32

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'
 'F'  'F'   0.0727   0.0534
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0311   0.0180
 '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'
 'S'  'S'   0.3331   0.5567
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_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                    11.1866(2)
_cell_length_b                    8.4898(2)
_cell_length_c                    16.1108(3)
_cell_angle_alpha                 90
_cell_angle_beta                  91.2670(10)
_cell_angle_gamma                 90
_cell_volume                      1529.70(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     193(2)
_cell_measurement_reflns_used                      25729
_cell_measurement_theta_min                        3.96
_cell_measurement_theta_max                        68.23
 
_exptl_crystal_description                         block
_exptl_crystal_colour                              colorless
_exptl_crystal_density_diffrn     1.586          
_exptl_crystal_F_000              752
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.550
_exptl_crystal_size_mid           0.350
_exptl_crystal_size_min           0.300
_exptl_absorpt_coefficient_mu     2.464
_shelx_estimated_absorpt_T_min    0.344
_shelx_estimated_absorpt_T_max    0.525
_exptl_absorpt_correction_type                     numerical
_exptl_absorpt_process_details                    'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min                    0.209
_exptl_absorpt_correction_T_max                    0.477
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       193(2)
_diffrn_radiation_wavelength      1.54187
_diffrn_radiation_type            CuK\a
_diffrn_source                    'Rotating anode'
_diffrn_measurement_device_type                   'Rigaku R-AXIS RAPID'
_diffrn_measurement_method                         ω
_diffrn_detector_area_resol_mean                   10.000
_diffrn_reflns_number             27368
_diffrn_reflns_av_unetI/netI      0.0151
_diffrn_reflns_av_R_equivalents   0.0393
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          4.764
_diffrn_reflns_theta_max          68.233
_diffrn_reflns_theta_full         67.687
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   1.000
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              2801
_reflns_number_gt                 2686
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection                        'RAPID AUTO (Rigaku, 2004)'
_computing_cell_refinement                        'RAPID AUTO'
_computing_data_reduction                         'RAPID AUTO'
_computing_structure_solution       'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement   'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   'SHELXL-2014 (Sheldrick, 2014)'
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0683P)²+0.7417P] where P=(Fo²+2Fc²)/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          2801
_refine_ls_number_parameters      218
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0427
_refine_ls_R_factor_gt            0.0417
_refine_ls_wR_factor_ref          0.1132
_refine_ls_wR_factor_gt           0.1123
_refine_ls_goodness_of_fit_ref    1.079
_refine_ls_restrained_S_all       1.079
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.03347(4) 0.37486(5) 0.23721(3) 0.03039(16) Uani 1 1 d . . . . .
F1 F 0.23607(12) 0.45279(19) 0.31012(8) 0.0602(4) Uani 1 1 d . . . . .
F2 F 0.18192(13) 0.60249(17) 0.20780(10) 0.0660(4) Uani 1 1 d . . . . .
F3 F 0.25194(12) 0.3727(2) 0.18515(10) 0.0697(5) Uani 1 1 d . . . . .
O1 O 0.53680(11) 0.37951(14) 0.26506(7) 0.0299(3) Uani 1 1 d . . . . .
O2 O 0.77882(11) 0.63374(14) 0.24594(8) 0.0320(3) Uani 1 1 d . . . . .
H2A H 0.8453 0.5920 0.2572 0.038 Uiso 1 1 calc R U . . .
O3 O -0.02742(12) 0.4854(2) 0.29027(9) 0.0477(4) Uani 1 1 d . . . . .
O4 O 0.04895(14) 0.22107(18) 0.27237(10) 0.0513(4) Uani 1 1 d . . . . .
O5 O -0.00606(14) 0.37962(19) 0.15213(9) 0.0483(4) Uani 1 1 d . . . . .
N1 N 0.68904(12) 0.53738(17) 0.27221(8) 0.0264(3) Uani 1 1 d . . . . .
C1 C 0.62200(14) 0.4498(2) 0.22404(10) 0.0263(4) Uani 1 1 d . . . . .
C2 C 0.53611(16) 0.4475(2) 0.35088(10) 0.0302(4) Uani 1 1 d . . . . .
H2 H 0.4713 0.5283 0.3536 0.036 Uiso 1 1 calc R U . . .
C3 C 0.51264(18) 0.3218(2) 0.41272(12) 0.0375(4) Uani 1 1 d . . . . .
H3 H 0.4456 0.2547 0.4042 0.045 Uiso 1 1 calc R U . . .
C4 C 0.58210(19) 0.3006(2) 0.47924(12) 0.0410(5) Uani 1 1 d . . . . .
H4 H 0.5580 0.2265 0.5198 0.049 Uiso 1 1 calc R U . . .
C5 C 0.69674(19) 0.3879(3) 0.49357(12) 0.0420(5) Uani 1 1 d . . . . .
H5A H 0.7543 0.3196 0.5242 0.050 Uiso 1 1 calc R U . . .
H5B H 0.6819 0.4821 0.5280 0.050 Uiso 1 1 calc R U . . .
C6 C 0.75024(16) 0.4384(2) 0.41135(11) 0.0336(4) Uani 1 1 d . . . . .
H6A H 0.8213 0.5055 0.4221 0.040 Uiso 1 1 calc R U . . .
H6B H 0.7759 0.3443 0.3801 0.040 Uiso 1 1 calc R U . . .
C7 C 0.65700(15) 0.5298(2) 0.36023(10) 0.0288(4) Uani 1 1 d . . . . .
H7 H 0.6468 0.6382 0.3833 0.035 Uiso 1 1 calc R U . . .
C8 C 0.63038(15) 0.4184(2) 0.13512(10) 0.0278(4) Uani 1 1 d . . . . .
C9 C 0.72756(16) 0.4676(2) 0.08859(11) 0.0339(4) Uani 1 1 d . . . . .
H9 H 0.7903 0.5274 0.1139 0.041 Uiso 1 1 calc R U . . .
C10 C 0.73145(19) 0.4283(3) 0.00527(12) 0.0413(5) Uani 1 1 d . . . . .
H10 H 0.7975 0.4609 -0.0266 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6403(2) 0.3421(3) -0.03200(12) 0.0436(5) Uani 1 1 d . . . . .
H11 H 0.6434 0.3170 -0.0894 0.052 Uiso 1 1 calc R U . . .
C12 C 0.5448(2) 0.2926(3) 0.01416(12) 0.0440(5) Uani 1 1 d . . . . .
H12 H 0.4828 0.2322 -0.0115 0.053 Uiso 1 1 calc R U . . .
C13 C 0.53873(17) 0.3303(2) 0.09763(12) 0.0366(4) Uani 1 1 d . . . . .
H13 H 0.4727 0.2964 0.1291 0.044 Uiso 1 1 calc R U . . .
C14 C 0.18384(17) 0.4555(3) 0.23550(12) 0.0393(4) Uani 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
S1 O5 1.4315(15) . ?
S1 O4 1.4323(16) . ?
S1 O3 1.4496(15) . ?
S1 C14 1.8167(19) . ?
F1 C14 1.325(2) . ?
F2 C14 1.326(3) . ?
F3 C14 1.327(2) . ?
O1 C1 1.315(2) . ?
O1 C2 1.499(2) . ?
O2 N1 1.3696(18) . ?
O2 H2A 0.8400 . ?
N1 C1 1.301(2) . ?
N1 C7 1.472(2) . ?
C1 C8 1.462(2) . ?
C2 C3 1.487(3) . ?
C2 C7 1.527(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.322(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.495(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.527(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.527(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?
C8 C13 1.396(3) . ?
C8 C9 1.398(3) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
 
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
O5 S1 O4 115.89(10) . . ?
O5 S1 O3 114.03(9) . . ?
O4 S1 O3 114.28(10) . . ?
O5 S1 C14 103.97(9) . . ?
O4 S1 C14 104.21(9) . . ?
O3 S1 C14 102.26(9) . . ?
C1 O1 C2 107.90(13) . . ?
N1 O2 H2A 109.5 . . ?
C1 N1 O2 125.05(14) . . ?
C1 N1 C7 113.60(14) . . ?
O2 N1 C7 121.31(13) . . ?
N1 C1 O1 111.99(15) . . ?
N1 C1 C8 129.80(16) . . ?
O1 C1 C8 118.20(15) . . ?
C3 C2 O1 110.25(15) . . ?
C3 C2 C7 115.55(16) . . ?
O1 C2 C7 104.17(12) . . ?
C3 C2 H2 108.9 . . ?
O1 C2 H2 108.9 . . ?
C7 C2 H2 108.9 . . ?
C4 C3 C2 122.11(19) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 123.00(18) . . ?
C3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C4 C5 C6 110.89(16) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 109.55(15) . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N1 C7 C6 111.35(14) . . ?
N1 C7 C2 99.14(13) . . ?
C6 C7 C2 114.45(15) . . ?
N1 C7 H7 110.5 . . ?
C6 C7 H7 110.5 . . ?
C2 C7 H7 110.5 . . ?
C13 C8 C9 120.04(16) . . ?
C13 C8 C1 117.34(16) . . ?
C9 C8 C1 122.57(16) . . ?
C10 C9 C8 119.28(18) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 120.69(19) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.99(18) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.47(19) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.52(18) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
F1 C14 F2 108.97(18) . . ?
F1 C14 F3 107.34(17) . . ?
F2 C14 F3 107.36(17) . . ?
F1 C14 S1 111.70(13) . . ?
F2 C14 S1 110.59(14) . . ?
F3 C14 S1 110.74(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
O2 N1 C1 O1 -174.76(14) . . . . ?
C7 N1 C1 O1 2.9(2) . . . . ?
O2 N1 C1 C8 6.7(3) . . . . ?
C7 N1 C1 C8 -175.68(16) . . . . ?
C2 O1 C1 N1 9.14(19) . . . . ?
C2 O1 C1 C8 -172.10(14) . . . . ?
C1 O1 C2 C3 -141.28(15) . . . . ?
C1 O1 C2 C7 -16.72(17) . . . . ?
O1 C2 C3 C4 128.66(19) . . . . ?
C7 C2 C3 C4 10.9(3) . . . . ?
C2 C3 C4 C5 -6.9(3) . . . . ?
C3 C4 C5 C6 -26.5(3) . . . . ?
C4 C5 C6 C7 53.4(2) . . . . ?
C1 N1 C7 C6 107.98(17) . . . . ?
O2 N1 C7 C6 -74.26(19) . . . . ?
C1 N1 C7 C2 -12.88(18) . . . . ?
O2 N1 C7 C2 164.87(14) . . . . ?
C5 C6 C7 N1 -162.00(15) . . . . ?
C5 C6 C7 C2 -50.6(2) . . . . ?
C3 C2 C7 N1 137.69(15) . . . . ?
O1 C2 C7 N1 16.60(16) . . . . ?
C3 C2 C7 C6 19.1(2) . . . . ?
O1 C2 C7 C6 -101.97(16) . . . . ?
N1 C1 C8 C13 -174.14(18) . . . . ?
O1 C1 C8 C13 7.4(2) . . . . ?
N1 C1 C8 C9 8.4(3) . . . . ?
O1 C1 C8 C9 -170.09(16) . . . . ?
C13 C8 C9 C10 0.1(3) . . . . ?
C1 C8 C9 C10 177.53(17) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C12 C13 C8 -0.3(3) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
C1 C8 C13 C12 -177.69(17) . . . . ?
O5 S1 C14 F1 -177.15(15) . . . . ?
O4 S1 C14 F1 -55.34(18) . . . . ?
O3 S1 C14 F1 63.94(17) . . . . ?
O5 S1 C14 F2 61.30(17) . . . . ?
O4 S1 C14 F2 -176.89(15) . . . . ?
O3 S1 C14 F2 -57.61(17) . . . . ?
O5 S1 C14 F3 -57.57(16) . . . . ?
O4 S1 C14 F3 64.24(16) . . . . ?
O3 S1 C14 F3 -176.49(14) . . . . ?
 
_refine_diff_density_max    0.246
_refine_diff_density_min   -0.451
_refine_diff_density_rms    0.071


