 
data_t 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C17 H14 F N O S' 
_chemical_formula_weight          299.35 
  
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' 
 'S'  'S'   0.1246   0.1234 
 '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' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/c' 
_space_group_name_Hall            '-P 2ybc' 
  
_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, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
  
_cell_length_a                    14.854(4) 
_cell_length_b                    13.222(3) 
_cell_length_c                    7.5070(18) 
_cell_angle_alpha                 90 
_cell_angle_beta                  102.901(4) 
_cell_angle_gamma                 90 
_cell_volume                      1437.2(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     3264 
_cell_measurement_theta_min       2.81 
_cell_measurement_theta_max       29.99 
  
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_density_meas       0 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.383 
_exptl_crystal_F_000              624 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.120 
_exptl_crystal_size_mid           0.100 
_exptl_crystal_size_min           0.100 
_exptl_absorpt_coefficient_mu     0.234 
_shelx_estimated_absorpt_T_min    0.972 
_shelx_estimated_absorpt_T_max    0.977 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             12093 
_diffrn_reflns_av_unetI/netI      0.0388 
_diffrn_reflns_av_R_equivalents   0.0317 
_diffrn_reflns_limit_h_min        -20 
_diffrn_reflns_limit_h_max        20 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        17 
_diffrn_reflns_limit_l_min        -8 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          1.406 
_diffrn_reflns_theta_max          29.997 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.995 
_diffrn_measured_fraction_theta_full  0.997 
_diffrn_reflns_Laue_measured_fraction_max    0.995 
_diffrn_reflns_Laue_measured_fraction_full   0.997 
_diffrn_reflns_point_group_measured_fraction_max   0.995 
_diffrn_reflns_point_group_measured_fraction_full  0.997 
_reflns_number_total              4191 
_reflns_number_gt                 3125 
_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        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_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)+(0.0715P)²+0.2468P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014' 
_refine_ls_extinction_coef        0.0018(18) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          4191 
_refine_ls_number_parameters      191 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0637 
_refine_ls_R_factor_gt            0.0460 
_refine_ls_wR_factor_ref          0.1422 
_refine_ls_wR_factor_gt           0.1278 
_refine_ls_goodness_of_fit_ref    1.063 
_refine_ls_restrained_S_all       1.063 
_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 
C1 C -0.10250(12) 0.62838(15) 0.0963(3) 0.0478(5) Uani 1 1 d . . . . . 
C2 C -0.02973(14) 0.69378(15) 0.1228(3) 0.0586(6) Uani 1 1 d . . . . . 
H2 H -0.0368 0.7603 0.0737 0.070 Uiso 1 1 calc R U . . . 
C3 C 0.05477(13) 0.66024(13) 0.2235(3) 0.0471(5) Uani 1 1 d . . . . . 
H3 H 0.1064 0.7045 0.2458 0.057 Uiso 1 1 calc R U . . . 
C4 C 0.06432(10) 0.56322(11) 0.2913(2) 0.0316(3) Uani 1 1 d . . . . . 
C5 C -0.01171(11) 0.49934(13) 0.2585(2) 0.0369(4) Uani 1 1 d . . . . . 
H5 H -0.0054 0.4320 0.3039 0.044 Uiso 1 1 calc R U . . . 
C6 C -0.09608(11) 0.53244(15) 0.1611(3) 0.0434(4) Uani 1 1 d . . . . . 
H6 H -0.1485 0.4892 0.1398 0.052 Uiso 1 1 calc R U . . . 
C7 C 0.15365(10) 0.52369(12) 0.3957(2) 0.0339(3) Uani 1 1 d . . . . . 
C8 C 0.23214(10) 0.59788(11) 0.4620(2) 0.0330(3) Uani 1 1 d . . . . . 
C9 C 0.37796(10) 0.67053(11) 0.4430(2) 0.0299(3) Uani 1 1 d . . . . . 
H9A H 0.3939 0.6671 0.5781 0.036 Uiso 1 1 calc R U . . . 
H9B H 0.3593 0.7409 0.4080 0.036 Uiso 1 1 calc R U . . . 
C10 C 0.46233(9) 0.64544(11) 0.37303(19) 0.0273(3) Uani 1 1 d . . . . . 
C11 C 0.47010(10) 0.55633(11) 0.28000(19) 0.0283(3) Uani 1 1 d . . . . . 
C12 C 0.38807(10) 0.48768(11) 0.2295(2) 0.0313(3) Uani 1 1 d . . . . . 
H12A H 0.3904 0.4363 0.3264 0.038 Uiso 1 1 calc R U . . . 
H12B H 0.3894 0.4520 0.1142 0.038 Uiso 1 1 calc R U . . . 
C13 C 0.29988(10) 0.54829(12) 0.2061(2) 0.0328(3) Uani 1 1 d . . . . . 
H13A H 0.2953 0.5964 0.1035 0.039 Uiso 1 1 calc R U . . . 
H13B H 0.2459 0.5024 0.1773 0.039 Uiso 1 1 calc R U . . . 
C14 C 0.55385(11) 0.53369(13) 0.2349(2) 0.0359(3) Uani 1 1 d . . . . . 
H14 H 0.5599 0.4729 0.1711 0.043 Uiso 1 1 calc R U . . . 
C15 C 0.62826(11) 0.59862(15) 0.2820(2) 0.0413(4) Uani 1 1 d . . . . . 
H15 H 0.6854 0.5815 0.2530 0.050 Uiso 1 1 calc R U . . . 
C16 C 0.61985(11) 0.68777(15) 0.3705(2) 0.0412(4) Uani 1 1 d . . . . . 
H16 H 0.6707 0.7329 0.4008 0.049 Uiso 1 1 calc R U . . . 
C17 C 0.53700(10) 0.71151(12) 0.4154(2) 0.0344(3) Uani 1 1 d . . . . . 
H17 H 0.5310 0.7735 0.4757 0.041 Uiso 1 1 calc R U . . . 
F1 F -0.18575(9) 0.66025(10) 0.0005(2) 0.0797(5) Uani 1 1 d . . . . . 
N1 N 0.29957(8) 0.60368(9) 0.37453(17) 0.0286(3) Uani 1 1 d . . . . . 
O1 O 0.16568(9) 0.43591(9) 0.4389(2) 0.0484(3) Uani 1 1 d . . . . . 
S1 S 0.22561(3) 0.66105(4) 0.64946(7) 0.04716(17) 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 
C1 F1 1.351(2) . ? 
C1 C6 1.354(3) . ? 
C1 C2 1.364(3) . ? 
C2 C3 1.386(3) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.376(2) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.388(2) . ? 
C4 C7 1.478(2) . ? 
C5 C6 1.374(2) . ? 
C5 H5 0.9500 . ? 
C6 H6 0.9500 . ? 
C7 O1 1.208(2) . ? 
C7 C8 1.520(2) . ? 
C8 N1 1.317(2) . ? 
C8 S1 1.6577(17) . ? 
C9 N1 1.4609(17) . ? 
C9 C10 1.500(2) . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C10 C11 1.388(2) . ? 
C10 C17 1.392(2) . ? 
C11 C14 1.393(2) . ? 
C11 C12 1.499(2) . ? 
C12 C13 1.512(2) . ? 
C12 H12A 0.9900 . ? 
C12 H12B 0.9900 . ? 
C13 N1 1.462(2) . ? 
C13 H13A 0.9900 . ? 
C13 H13B 0.9900 . ? 
C14 C15 1.382(2) . ? 
C14 H14 0.9500 . ? 
C15 C16 1.372(3) . ? 
C15 H15 0.9500 . ? 
C16 C17 1.383(2) . ? 
C16 H16 0.9500 . ? 
C17 H17 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 
F1 C1 C6 117.75(17) . . ? 
F1 C1 C2 118.77(18) . . ? 
C6 C1 C2 123.48(16) . . ? 
C1 C2 C3 117.94(18) . . ? 
C1 C2 H2 121.0 . . ? 
C3 C2 H2 121.0 . . ? 
C4 C3 C2 120.42(16) . . ? 
C4 C3 H3 119.8 . . ? 
C2 C3 H3 119.8 . . ? 
C3 C4 C5 119.30(15) . . ? 
C3 C4 C7 122.16(14) . . ? 
C5 C4 C7 118.53(14) . . ? 
C6 C5 C4 120.67(16) . . ? 
C6 C5 H5 119.7 . . ? 
C4 C5 H5 119.7 . . ? 
C1 C6 C5 118.18(16) . . ? 
C1 C6 H6 120.9 . . ? 
C5 C6 H6 120.9 . . ? 
O1 C7 C4 122.94(14) . . ? 
O1 C7 C8 118.41(14) . . ? 
C4 C7 C8 118.53(13) . . ? 
N1 C8 C7 119.18(14) . . ? 
N1 C8 S1 126.10(11) . . ? 
C7 C8 S1 114.66(12) . . ? 
N1 C9 C10 113.94(12) . . ? 
N1 C9 H9A 108.8 . . ? 
C10 C9 H9A 108.8 . . ? 
N1 C9 H9B 108.8 . . ? 
C10 C9 H9B 108.8 . . ? 
H9A C9 H9B 107.7 . . ? 
C11 C10 C17 119.77(14) . . ? 
C11 C10 C9 122.26(12) . . ? 
C17 C10 C9 117.81(14) . . ? 
C10 C11 C14 118.94(14) . . ? 
C10 C11 C12 119.17(13) . . ? 
C14 C11 C12 121.89(14) . . ? 
C11 C12 C13 110.04(12) . . ? 
C11 C12 H12A 109.7 . . ? 
C13 C12 H12A 109.7 . . ? 
C11 C12 H12B 109.7 . . ? 
C13 C12 H12B 109.7 . . ? 
H12A C12 H12B 108.2 . . ? 
N1 C13 C12 109.58(12) . . ? 
N1 C13 H13A 109.8 . . ? 
C12 C13 H13A 109.8 . . ? 
N1 C13 H13B 109.8 . . ? 
C12 C13 H13B 109.8 . . ? 
H13A C13 H13B 108.2 . . ? 
C15 C14 C11 120.75(16) . . ? 
C15 C14 H14 119.6 . . ? 
C11 C14 H14 119.6 . . ? 
C16 C15 C14 120.23(16) . . ? 
C16 C15 H15 119.9 . . ? 
C14 C15 H15 119.9 . . ? 
C15 C16 C17 119.68(15) . . ? 
C15 C16 H16 120.2 . . ? 
C17 C16 H16 120.2 . . ? 
C16 C17 C10 120.60(16) . . ? 
C16 C17 H17 119.7 . . ? 
C10 C17 H17 119.7 . . ? 
C8 N1 C9 119.68(13) . . ? 
C8 N1 C13 123.48(12) . . ? 
C9 N1 C13 116.81(12) . . ? 
  
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 
F1 C1 C2 C3 179.1(2) . . . . ? 
C6 C1 C2 C3 -0.9(4) . . . . ? 
C1 C2 C3 C4 1.0(3) . . . . ? 
C2 C3 C4 C5 -0.3(3) . . . . ? 
C2 C3 C4 C7 178.57(19) . . . . ? 
C3 C4 C5 C6 -0.7(3) . . . . ? 
C7 C4 C5 C6 -179.56(16) . . . . ? 
F1 C1 C6 C5 179.98(18) . . . . ? 
C2 C1 C6 C5 -0.1(3) . . . . ? 
C4 C5 C6 C1 0.8(3) . . . . ? 
C3 C4 C7 O1 -171.66(19) . . . . ? 
C5 C4 C7 O1 7.2(3) . . . . ? 
C3 C4 C7 C8 12.3(3) . . . . ? 
C5 C4 C7 C8 -168.84(15) . . . . ? 
O1 C7 C8 N1 80.6(2) . . . . ? 
C4 C7 C8 N1 -103.19(18) . . . . ? 
O1 C7 C8 S1 -96.54(18) . . . . ? 
C4 C7 C8 S1 79.67(17) . . . . ? 
N1 C9 C10 C11 -11.2(2) . . . . ? 
N1 C9 C10 C17 173.29(13) . . . . ? 
C17 C10 C11 C14 1.6(2) . . . . ? 
C9 C10 C11 C14 -173.78(13) . . . . ? 
C17 C10 C11 C12 -177.87(13) . . . . ? 
C9 C10 C11 C12 6.7(2) . . . . ? 
C10 C11 C12 C13 27.77(18) . . . . ? 
C14 C11 C12 C13 -151.71(14) . . . . ? 
C11 C12 C13 N1 -57.34(16) . . . . ? 
C10 C11 C14 C15 0.1(2) . . . . ? 
C12 C11 C14 C15 179.56(14) . . . . ? 
C11 C14 C15 C16 -1.5(2) . . . . ? 
C14 C15 C16 C17 1.2(2) . . . . ? 
C15 C16 C17 C10 0.5(2) . . . . ? 
C11 C10 C17 C16 -2.0(2) . . . . ? 
C9 C10 C17 C16 173.65(14) . . . . ? 
C7 C8 N1 C9 -176.58(13) . . . . ? 
S1 C8 N1 C9 0.2(2) . . . . ? 
C7 C8 N1 C13 5.3(2) . . . . ? 
S1 C8 N1 C13 -177.96(12) . . . . ? 
C10 C9 N1 C8 160.53(13) . . . . ? 
C10 C9 N1 C13 -21.18(18) . . . . ? 
C12 C13 N1 C8 -126.02(15) . . . . ? 
C12 C13 N1 C9 55.76(17) . . . . ? 
  
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 
C13 H13B F1  0.99 2.58 3.422(2) 142.5 3_565 
C9 H9B S1  0.99 2.77 3.5649(16) 137.8 4_575 
C6 H6 S1  0.95 2.93 3.673(2) 136.2 3_566 
C13 H13B F1  0.99 2.58 3.422(2) 142.5 3_565 
C9 H9B S1  0.99 2.77 3.5649(16) 137.8 4_575 
C6 H6 S1  0.95 2.93 3.673(2) 136.2 3_566 
C6 H6 S1  0.95 2.93 3.673(2) 136.2 3_566 
C9 H9B S1  0.99 2.77 3.5649(16) 137.8 4_575 
C13 H13B F1  0.99 2.58 3.422(2) 142.5 3_565 
  
_refine_diff_density_max    0.309 
_refine_diff_density_min   -0.358 
_refine_diff_density_rms    0.054 
  
  
  
