 
data_mo_d8v20749_0m 
  
_audit_creation_method            SHELXL-2013 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C19 H18 F N O2 S' 
_chemical_formula_weight          343.40 
  
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' 
 'F'  'F'   0.0171   0.0103 
 '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' 
  
_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                    8.7423(3) 
_cell_length_b                    16.0218(5) 
_cell_length_c                    11.8664(4) 
_cell_angle_alpha                 90 
_cell_angle_beta                  103.6720(10) 
_cell_angle_gamma                 90 
_cell_volume                      1615.00(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     9913 
_cell_measurement_theta_min       5.241 
_cell_measurement_theta_max       54.872 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.412 
_exptl_crystal_F_000              720 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.170 
_exptl_crystal_size_mid           0.150 
_exptl_crystal_size_min           0.120 
_exptl_absorpt_coefficient_mu     0.222 
_shelx_estimated_absorpt_T_min    0.963 
_shelx_estimated_absorpt_T_max    0.974 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6553 
_exptl_absorpt_correction_T_max   0.7456 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(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             21609 
_diffrn_reflns_av_unetI/netI      0.0201 
_diffrn_reflns_av_R_equivalents   0.0335 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -19 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          2.542 
_diffrn_reflns_theta_max          25.995 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.992 
_diffrn_measured_fraction_theta_full  0.992 
_diffrn_reflns_Laue_measured_fraction_max    0.992 
_diffrn_reflns_Laue_measured_fraction_full   0.992 
_diffrn_reflns_point_group_measured_fraction_max   0.992 
_diffrn_reflns_point_group_measured_fraction_full  0.992 
_reflns_number_total              3145 
_reflns_number_gt                 2751 
_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-2013 (Sheldrick, 2013)' 
_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)+(0.0498P)²+0.9488P] 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      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          3145 
_refine_ls_number_parameters      218 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0483 
_refine_ls_R_factor_gt            0.0417 
_refine_ls_wR_factor_ref          0.1119 
_refine_ls_wR_factor_gt           0.1060 
_refine_ls_goodness_of_fit_ref    1.032 
_refine_ls_restrained_S_all       1.032 
_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 -0.17763(5) 0.59106(3) 0.28164(4) 0.04002(16) Uani 1 1 d . . . . . 
F1 F 0.79465(15) 0.70951(9) 0.67565(12) 0.0646(4) Uani 1 1 d . . . . . 
O1 O -0.27775(17) 0.57998(10) 0.16780(14) 0.0594(4) Uani 1 1 d . . . . . 
O2 O -0.25099(18) 0.58694(10) 0.37706(15) 0.0601(4) Uani 1 1 d . . . . . 
N1 N -0.03135(18) 0.52390(9) 0.30899(15) 0.0411(4) Uani 1 1 d . . . . . 
C1 C -0.0746(2) 0.68694(11) 0.28064(16) 0.0354(4) Uani 1 1 d . . . . . 
H1 H -0.0475 0.6929 0.2055 0.043 Uiso 1 1 calc R U . . . 
C2 C -0.1791(3) 0.76113(14) 0.2976(2) 0.0526(5) Uani 1 1 d . . . . . 
H2A H -0.2197 0.7900 0.2248 0.063 Uiso 1 1 calc R U . . . 
H2B H -0.2669 0.7423 0.3279 0.063 Uiso 1 1 calc R U . . . 
C3 C -0.0721(3) 0.81749(15) 0.3835(2) 0.0634(6) Uani 1 1 d . . . . . 
H3A H -0.1315 0.8475 0.4300 0.076 Uiso 1 1 calc R U . . . 
H3B H -0.0207 0.8576 0.3436 0.076 Uiso 1 1 calc R U . . . 
C4 C 0.0476(3) 0.76065(13) 0.45869(19) 0.0500(5) Uani 1 1 d . . . . . 
H4A H 0.1443 0.7905 0.4918 0.060 Uiso 1 1 calc R U . . . 
H4B H 0.0069 0.7369 0.5209 0.060 Uiso 1 1 calc R U . . . 
C5 C 0.0746(2) 0.69376(11) 0.37601(16) 0.0358(4) Uani 1 1 d . . . . . 
C6 C 0.2069(2) 0.65184(10) 0.37422(15) 0.0335(4) Uani 1 1 d . . . . . 
C7 C 0.21046(19) 0.58939(10) 0.28288(14) 0.0312(4) Uani 1 1 d . . . . . 
C8 C 0.3371(2) 0.58746(11) 0.22928(16) 0.0365(4) Uani 1 1 d . . . . . 
H8 H 0.4219 0.6232 0.2553 0.044 Uiso 1 1 calc R U . . . 
C9 C 0.3386(2) 0.53374(12) 0.13887(17) 0.0429(4) Uani 1 1 d . . . . . 
H9 H 0.4238 0.5337 0.1044 0.051 Uiso 1 1 calc R U . . . 
C10 C 0.2138(2) 0.47993(13) 0.09926(17) 0.0468(5) Uani 1 1 d . . . . . 
H10 H 0.2132 0.4449 0.0366 0.056 Uiso 1 1 calc R U . . . 
C11 C 0.0904(2) 0.47844(12) 0.15308(17) 0.0430(4) Uani 1 1 d . . . . . 
H11 H 0.0075 0.4414 0.1275 0.052 Uiso 1 1 calc R U . . . 
C12 C 0.0885(2) 0.53161(10) 0.24518(15) 0.0334(4) Uani 1 1 d . . . . . 
C13 C 0.3598(2) 0.66858(11) 0.45831(15) 0.0345(4) Uani 1 1 d . . . . . 
C14 C 0.4348(2) 0.74533(11) 0.45993(16) 0.0394(4) Uani 1 1 d . . . . . 
H14 H 0.3860 0.7877 0.4108 0.047 Uiso 1 1 calc R U . . . 
C15 C 0.5807(2) 0.75970(12) 0.53337(16) 0.0427(4) Uani 1 1 d . . . . . 
H15 H 0.6306 0.8111 0.5342 0.051 Uiso 1 1 calc R U . . . 
C16 C 0.6497(2) 0.69625(13) 0.60479(16) 0.0427(5) Uani 1 1 d . . . . . 
C17 C 0.5804(2) 0.61985(13) 0.60694(17) 0.0445(5) Uani 1 1 d . . . . . 
H17 H 0.6301 0.5782 0.6571 0.053 Uiso 1 1 calc R U . . . 
C18 C 0.4346(2) 0.60597(12) 0.53270(16) 0.0399(4) Uani 1 1 d . . . . . 
H18 H 0.3861 0.5543 0.5325 0.048 Uiso 1 1 calc R U . . . 
C19 C -0.0650(4) 0.44162(16) 0.3490(3) 0.0897(10) Uani 1 1 d . . . . . 
H19A H -0.1269 0.4473 0.4055 0.135 Uiso 1 1 calc R U . . . 
H19B H 0.0321 0.4138 0.3836 0.135 Uiso 1 1 calc R U . . . 
H19C H -0.1222 0.4095 0.2845 0.135 Uiso 1 1 calc R U . . . 
  
  
_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 O2 1.4287(16) . ? 
S1 O1 1.4365(16) . ? 
S1 N1 1.6439(16) . ? 
S1 C1 1.7823(18) . ? 
F1 C16 1.362(2) . ? 
N1 C12 1.436(2) . ? 
N1 C19 1.455(3) . ? 
C1 C5 1.515(3) . ? 
C1 C2 1.541(3) . ? 
C1 H1 0.9800 . ? 
C2 C3 1.509(3) . ? 
C2 H2A 0.9700 . ? 
C2 H2B 0.9700 . ? 
C3 C4 1.510(3) . ? 
C3 H3A 0.9700 . ? 
C3 H3B 0.9700 . ? 
C4 C5 1.509(3) . ? 
C4 H4A 0.9700 . ? 
C4 H4B 0.9700 . ? 
C5 C6 1.342(3) . ? 
C6 C7 1.481(2) . ? 
C6 C13 1.491(2) . ? 
C7 C8 1.401(2) . ? 
C7 C12 1.403(2) . ? 
C8 C9 1.378(3) . ? 
C8 H8 0.9300 . ? 
C9 C10 1.383(3) . ? 
C9 H9 0.9300 . ? 
C10 C11 1.378(3) . ? 
C10 H10 0.9300 . ? 
C11 C12 1.389(3) . ? 
C11 H11 0.9300 . ? 
C13 C14 1.392(3) . ? 
C13 C18 1.393(3) . ? 
C14 C15 1.384(3) . ? 
C14 H14 0.9300 . ? 
C15 C16 1.369(3) . ? 
C15 H15 0.9300 . ? 
C16 C17 1.369(3) . ? 
C17 C18 1.386(3) . ? 
C17 H17 0.9300 . ? 
C18 H18 0.9300 . ? 
C19 H19A 0.9600 . ? 
C19 H19B 0.9600 . ? 
C19 H19C 0.9600 . ? 
  
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 
O2 S1 O1 116.86(10) . . ? 
O2 S1 N1 106.70(9) . . ? 
O1 S1 N1 112.17(9) . . ? 
O2 S1 C1 111.55(10) . . ? 
O1 S1 C1 107.27(9) . . ? 
N1 S1 C1 101.23(8) . . ? 
C12 N1 C19 118.63(17) . . ? 
C12 N1 S1 118.05(12) . . ? 
C19 N1 S1 116.74(16) . . ? 
C5 C1 C2 106.20(15) . . ? 
C5 C1 S1 113.85(12) . . ? 
C2 C1 S1 110.36(13) . . ? 
C5 C1 H1 108.8 . . ? 
C2 C1 H1 108.8 . . ? 
S1 C1 H1 108.8 . . ? 
C3 C2 C1 104.96(17) . . ? 
C3 C2 H2A 110.8 . . ? 
C1 C2 H2A 110.8 . . ? 
C3 C2 H2B 110.8 . . ? 
C1 C2 H2B 110.8 . . ? 
H2A C2 H2B 108.8 . . ? 
C2 C3 C4 105.69(18) . . ? 
C2 C3 H3A 110.6 . . ? 
C4 C3 H3A 110.6 . . ? 
C2 C3 H3B 110.6 . . ? 
C4 C3 H3B 110.6 . . ? 
H3A C3 H3B 108.7 . . ? 
C5 C4 C3 103.71(17) . . ? 
C5 C4 H4A 111.0 . . ? 
C3 C4 H4A 111.0 . . ? 
C5 C4 H4B 111.0 . . ? 
C3 C4 H4B 111.0 . . ? 
H4A C4 H4B 109.0 . . ? 
C6 C5 C4 129.32(17) . . ? 
C6 C5 C1 123.02(16) . . ? 
C4 C5 C1 107.32(15) . . ? 
C5 C6 C7 121.15(16) . . ? 
C5 C6 C13 122.62(16) . . ? 
C7 C6 C13 116.13(15) . . ? 
C8 C7 C12 117.57(16) . . ? 
C8 C7 C6 120.19(15) . . ? 
C12 C7 C6 122.23(16) . . ? 
C9 C8 C7 121.44(17) . . ? 
C9 C8 H8 119.3 . . ? 
C7 C8 H8 119.3 . . ? 
C8 C9 C10 120.11(18) . . ? 
C8 C9 H9 119.9 . . ? 
C10 C9 H9 119.9 . . ? 
C11 C10 C9 119.65(18) . . ? 
C11 C10 H10 120.2 . . ? 
C9 C10 H10 120.2 . . ? 
C10 C11 C12 120.69(18) . . ? 
C10 C11 H11 119.7 . . ? 
C12 C11 H11 119.7 . . ? 
C11 C12 C7 120.42(17) . . ? 
C11 C12 N1 120.54(16) . . ? 
C7 C12 N1 118.87(16) . . ? 
C14 C13 C18 118.59(17) . . ? 
C14 C13 C6 120.86(16) . . ? 
C18 C13 C6 120.46(16) . . ? 
C15 C14 C13 121.13(18) . . ? 
C15 C14 H14 119.4 . . ? 
C13 C14 H14 119.4 . . ? 
C16 C15 C14 118.17(18) . . ? 
C16 C15 H15 120.9 . . ? 
C14 C15 H15 120.9 . . ? 
F1 C16 C17 118.64(18) . . ? 
F1 C16 C15 118.42(18) . . ? 
C17 C16 C15 122.94(18) . . ? 
C16 C17 C18 118.44(18) . . ? 
C16 C17 H17 120.8 . . ? 
C18 C17 H17 120.8 . . ? 
C17 C18 C13 120.73(18) . . ? 
C17 C18 H18 119.6 . . ? 
C13 C18 H18 119.6 . . ? 
N1 C19 H19A 109.5 . . ? 
N1 C19 H19B 109.5 . . ? 
H19A C19 H19B 109.5 . . ? 
N1 C19 H19C 109.5 . . ? 
H19A C19 H19C 109.5 . . ? 
H19B C19 H19C 109.5 . . ? 
  
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 S1 N1 C12 -162.70(14) . . . . ? 
O1 S1 N1 C12 68.14(16) . . . . ? 
C1 S1 N1 C12 -45.92(16) . . . . ? 
O2 S1 N1 C19 46.1(2) . . . . ? 
O1 S1 N1 C19 -83.1(2) . . . . ? 
C1 S1 N1 C19 162.9(2) . . . . ? 
O2 S1 C1 C5 71.58(15) . . . . ? 
O1 S1 C1 C5 -159.27(13) . . . . ? 
N1 S1 C1 C5 -41.58(15) . . . . ? 
O2 S1 C1 C2 -47.72(17) . . . . ? 
O1 S1 C1 C2 81.44(16) . . . . ? 
N1 S1 C1 C2 -160.88(14) . . . . ? 
C5 C1 C2 C3 12.5(2) . . . . ? 
S1 C1 C2 C3 136.30(17) . . . . ? 
C1 C2 C3 C4 -29.8(2) . . . . ? 
C2 C3 C4 C5 35.5(2) . . . . ? 
C3 C4 C5 C6 145.8(2) . . . . ? 
C3 C4 C5 C1 -27.5(2) . . . . ? 
C2 C1 C5 C6 -164.47(18) . . . . ? 
S1 C1 C5 C6 73.9(2) . . . . ? 
C2 C1 C5 C4 9.4(2) . . . . ? 
S1 C1 C5 C4 -112.26(16) . . . . ? 
C4 C5 C6 C7 -178.27(18) . . . . ? 
C1 C5 C6 C7 -5.9(3) . . . . ? 
C4 C5 C6 C13 -2.1(3) . . . . ? 
C1 C5 C6 C13 170.30(16) . . . . ? 
C5 C6 C7 C8 136.25(18) . . . . ? 
C13 C6 C7 C8 -40.2(2) . . . . ? 
C5 C6 C7 C12 -42.6(2) . . . . ? 
C13 C6 C7 C12 141.03(16) . . . . ? 
C12 C7 C8 C9 3.2(2) . . . . ? 
C6 C7 C8 C9 -175.68(16) . . . . ? 
C7 C8 C9 C10 -0.2(3) . . . . ? 
C8 C9 C10 C11 -2.1(3) . . . . ? 
C9 C10 C11 C12 1.3(3) . . . . ? 
C10 C11 C12 C7 1.8(3) . . . . ? 
C10 C11 C12 N1 -173.33(17) . . . . ? 
C8 C7 C12 C11 -3.9(2) . . . . ? 
C6 C7 C12 C11 174.91(16) . . . . ? 
C8 C7 C12 N1 171.24(15) . . . . ? 
C6 C7 C12 N1 -9.9(2) . . . . ? 
C19 N1 C12 C11 48.5(3) . . . . ? 
S1 N1 C12 C11 -102.20(18) . . . . ? 
C19 N1 C12 C7 -126.7(2) . . . . ? 
S1 N1 C12 C7 82.64(19) . . . . ? 
C5 C6 C13 C14 -64.3(2) . . . . ? 
C7 C6 C13 C14 112.09(19) . . . . ? 
C5 C6 C13 C18 119.2(2) . . . . ? 
C7 C6 C13 C18 -64.4(2) . . . . ? 
C18 C13 C14 C15 0.1(3) . . . . ? 
C6 C13 C14 C15 -176.44(17) . . . . ? 
C13 C14 C15 C16 -0.1(3) . . . . ? 
C14 C15 C16 F1 178.76(17) . . . . ? 
C14 C15 C16 C17 -0.3(3) . . . . ? 
F1 C16 C17 C18 -178.47(17) . . . . ? 
C15 C16 C17 C18 0.6(3) . . . . ? 
C16 C17 C18 C13 -0.5(3) . . . . ? 
C14 C13 C18 C17 0.2(3) . . . . ? 
C6 C13 C18 C17 176.75(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 
C2 H2B O2  0.97 2.55 3.058(3) 112.5 . 
C2 H2B O2  0.97 2.55 3.058(3) 112.5 . 
C2 H2B O2  0.97 2.55 3.058(3) 112.5 . 
C2 H2B O2  0.97 2.55 3.058(3) 112.5 . 
  
_refine_diff_density_max    0.417 
_refine_diff_density_min   -0.289 
_refine_diff_density_rms    0.040 
  
_shelxl_version_number 2013-4 
  
  
  
