 
data_A25206O_014
 
_audit_creation_method            'SHELXL-2019/3'
_shelx_SHELXL_version_number      '2019/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C14 H10 F4 S'
_chemical_formula_sum
 'C14 H10 F4 S' 
_chemical_formula_weight          286.28

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'
 '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/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                    9.5486(6)
_cell_length_b                    7.5608(5)
_cell_length_c                    17.9953(10)
_cell_angle_alpha                 90
_cell_angle_beta                  98.1501(18)
_cell_angle_gamma                 90
_cell_volume                      1286.05(14)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     9916
_cell_measurement_theta_min       2.93
_cell_measurement_theta_max       28.01
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.479          
_exptl_crystal_F_000              584
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.191
_exptl_crystal_size_mid           0.117
_exptl_crystal_size_min           0.052
_exptl_absorpt_coefficient_mu     0.282
_shelx_estimated_absorpt_T_min    0.948
_shelx_estimated_absorpt_T_max    0.986
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.6951
_exptl_absorpt_correction_T_max   0.7456
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Ius 3.0 microfocus source'
_diffrn_measurement_device_type   'PHOTON II 14 CPAD detector'
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             31708
_diffrn_reflns_av_unetI/netI      0.0204
_diffrn_reflns_av_R_equivalents   0.0448
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          2.912
_diffrn_reflns_theta_max          28.017
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              3099
_reflns_number_gt                 2588
_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 APEX5 software' 
_computing_cell_refinement        'Bruker APEX5 software' 
_computing_data_reduction         'Bruker APEX5 software' 
_computing_structure_solution     'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics     ORTEP
_computing_publication_material   CIFTAB
_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)+(0.0308P)²+0.4296P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_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          3099
_refine_ls_number_parameters      248
_refine_ls_number_restraints      574
_refine_ls_R_factor_all           0.0481
_refine_ls_R_factor_gt            0.0369
_refine_ls_wR_factor_ref          0.0879
_refine_ls_wR_factor_gt           0.0805
_refine_ls_goodness_of_fit_ref    1.092
_refine_ls_restrained_S_all       1.026
_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 0.01803(7) 0.52926(11) 0.61035(4) 0.0353(2) Uani 0.803(2) 1 d D U P A 1
C2 C -0.0459(3) 0.4166(5) 0.6796(2) 0.0437(7) Uani 0.803(2) 1 d D U P A 1
H2 H -0.140866 0.376763 0.676599 0.052 Uiso 0.803(2) 1 calc R U P A 1
C3 C 0.0538(4) 0.3902(6) 0.73951(18) 0.0488(9) Uani 0.803(2) 1 d D U P A 1
H3 H 0.036730 0.329942 0.783675 0.059 Uiso 0.803(2) 1 calc R U P A 1
C4 C 0.1864(4) 0.4618(6) 0.7294(2) 0.0414(9) Uani 0.803(2) 1 d D U P A 1
H4 H 0.267517 0.456366 0.766629 0.050 Uiso 0.803(2) 1 calc R U P A 1
C5 C 0.1866(2) 0.5395(6) 0.6612(2) 0.0283(7) Uani 0.803(2) 1 d D U P A 1
C14 C 0.2638(5) 0.7868(3) 0.58325(18) 0.0315(8) Uani 0.803(2) 1 d G U P A 1
C15 C 0.2040(3) 0.9300(4) 0.61562(14) 0.0444(10) Uani 0.803(2) 1 d G U P A 1
H15 H 0.188971 0.924755 0.666644 0.053 Uiso 0.803(2) 1 calc R U P A 1
C16 C 0.16615(19) 1.0808(2) 0.57335(17) 0.0528(6) Uani 0.803(2) 1 d G U P A 1
H16 H 0.125250 1.178689 0.595478 0.063 Uiso 0.803(2) 1 calc R U P A 1
C17 C 0.1881(3) 1.0885(3) 0.49870(17) 0.0568(9) Uani 0.803(2) 1 d G U P A 1
H17 H 0.162269 1.191611 0.469806 0.068 Uiso 0.803(2) 1 calc R U P A 1
C18 C 0.2480(4) 0.9454(3) 0.46632(14) 0.0578(9) Uani 0.803(2) 1 d G U P A 1
H18 H 0.263009 0.950597 0.415299 0.069 Uiso 0.803(2) 1 calc R U P A 1
C19 C 0.2858(4) 0.7945(3) 0.50859(18) 0.0446(9) Uani 0.803(2) 1 d G U P A 1
H19 H 0.326731 0.696660 0.486464 0.053 Uiso 0.803(2) 1 calc R U P A 1
S1B S 0.1851(5) 0.9832(7) 0.6075(2) 0.0545(14) Uani 0.197(2) 1 d D U P A 2
C2B C 0.1838(17) 1.0961(16) 0.5285(7) 0.047(3) Uani 0.197(2) 1 d D U P A 2
H2B H 0.146337 1.212009 0.520513 0.057 Uiso 0.197(2) 1 calc R U P A 2
C3B C 0.2414(18) 1.0047(17) 0.4781(7) 0.047(3) Uani 0.197(2) 1 d D U P A 2
H3B H 0.245761 1.046386 0.428650 0.057 Uiso 0.197(2) 1 calc R U P A 2
C4B C 0.295(2) 0.8408(18) 0.5044(9) 0.042(3) Uani 0.197(2) 1 d D U P A 2
H4B H 0.342454 0.762919 0.474637 0.050 Uiso 0.197(2) 1 calc R U P A 2
C5B C 0.275(2) 0.8014(18) 0.5763(9) 0.035(3) Uani 0.197(2) 1 d D U P A 2
C14B C 0.1857(9) 0.565(2) 0.6507(8) 0.030(3) Uani 0.197(2) 1 d G U P A 2
C15B C 0.0615(10) 0.5420(17) 0.6011(5) 0.036(3) Uani 0.197(2) 1 d G U P A 2
H15B H 0.056127 0.581445 0.550650 0.044 Uiso 0.197(2) 1 calc R U P A 2
C16B C -0.0548(8) 0.4614(11) 0.6253(5) 0.0436(18) Uani 0.197(2) 1 d G U P A 2
H16B H -0.139712 0.445818 0.591417 0.052 Uiso 0.197(2) 1 calc R U P A 2
C17B C -0.0470(12) 0.4037(17) 0.6991(6) 0.042(3) Uani 0.197(2) 1 d G U P A 2
H17B H -0.126499 0.348595 0.715667 0.051 Uiso 0.197(2) 1 calc R U P A 2
C18B C 0.0772(17) 0.426(2) 0.7487(5) 0.043(3) Uani 0.197(2) 1 d G U P A 2
H18B H 0.082552 0.387000 0.799150 0.051 Uiso 0.197(2) 1 calc R U P A 2
C19B C 0.1935(13) 0.507(2) 0.7245(8) 0.038(3) Uani 0.197(2) 1 d G U P A 2
H19B H 0.278393 0.522627 0.758384 0.045 Uiso 0.197(2) 1 calc R U P A 2
C6 C 0.30331(14) 0.62803(18) 0.62741(7) 0.0311(3) Uani 1 1 d . U . . .
C7 C 0.43652(14) 0.56392(19) 0.63839(8) 0.0340(3) Uani 1 1 d . U . . .
C8 C 0.47265(15) 0.3916(2) 0.67715(8) 0.0407(3) Uani 1 1 d . U . . .
H8 H 0.387133 0.313886 0.672843 0.049 Uiso 1 1 calc R U . . .
F9 F 0.52558(11) 0.41749(16) 0.75119(6) 0.0615(3) Uani 1 1 d . U . . .
F10 F 0.57908(10) 0.30868(13) 0.64699(6) 0.0567(3) Uani 1 1 d . U . . .
C11 C 0.55551(15) 0.6686(2) 0.61477(9) 0.0434(4) Uani 1 1 d . U . . .
H11 H 0.525229 0.794086 0.605075 0.052 Uiso 1 1 calc R U . . .
F12 F 0.60210(11) 0.59957(14) 0.55252(6) 0.0597(3) Uani 1 1 d . U . . .
F13 F 0.67026(10) 0.66271(14) 0.66939(7) 0.0619(3) Uani 1 1 d . 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 C2 1.693(4) . ?
S1 C5 1.737(3) . ?
C2 C3 1.348(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.412(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.361(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.500(3) . ?
C14 C15 1.3900 . ?
C14 C19 1.3900 . ?
C14 C6 1.460(2) . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S1B C2B 1.656(11) . ?
S1B C5B 1.756(11) . ?
C2B C3B 1.321(14) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.399(13) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.368(12) . ?
C4B H4B 0.9500 . ?
C5B C6 1.602(12) . ?
C14B C6 1.341(9) . ?
C14B C15B 1.3900 . ?
C14B C19B 1.3900 . ?
C15B C16B 1.3900 . ?
C15B H15B 0.9500 . ?
C16B C17B 1.3900 . ?
C16B H16B 0.9500 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9500 . ?
C18B C19B 1.3900 . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?
C6 C7 1.3493(18) . ?
C7 C11 1.495(2) . ?
C7 C8 1.495(2) . ?
C8 F10 1.3700(17) . ?
C8 F9 1.3705(18) . ?
C8 H8 1.0000 . ?
C11 F13 1.3650(19) . ?
C11 F12 1.3661(18) . ?
C11 H11 1.0000 . ?
 
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
C2 S1 C5 92.20(14) . . ?
C3 C2 S1 112.1(2) . . ?
C3 C2 H2 124.0 . . ?
S1 C2 H2 124.0 . . ?
C2 C3 C4 112.6(2) . . ?
C2 C3 H3 123.7 . . ?
C4 C3 H3 123.7 . . ?
C5 C4 C3 113.4(2) . . ?
C5 C4 H4 123.3 . . ?
C3 C4 H4 123.3 . . ?
C4 C5 C6 130.9(2) . . ?
C4 C5 S1 109.64(19) . . ?
C6 C5 S1 119.5(2) . . ?
C15 C14 C19 120.0 . . ?
C15 C14 C6 120.14(19) . . ?
C19 C14 C6 119.86(19) . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.0 . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C2B S1B C5B 94.2(6) . . ?
C3B C2B S1B 111.5(8) . . ?
C3B C2B H2B 124.2 . . ?
S1B C2B H2B 124.2 . . ?
C2B C3B C4B 113.6(9) . . ?
C2B C3B H3B 123.2 . . ?
C4B C3B H3B 123.2 . . ?
C5B C4B C3B 114.7(9) . . ?
C5B C4B H4B 122.6 . . ?
C3B C4B H4B 122.6 . . ?
C4B C5B C6 133.4(10) . . ?
C4B C5B S1B 105.8(7) . . ?
C6 C5B S1B 120.4(9) . . ?
C6 C14B C15B 121.3(9) . . ?
C6 C14B C19B 118.4(9) . . ?
C15B C14B C19B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C17B C16B C15B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C16B C17B C18B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C19B C18B C17B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C18B C19B C14B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C14B C19B H19B 120.0 . . ?
C14B C6 C7 129.8(6) . . ?
C7 C6 C14 122.7(2) . . ?
C7 C6 C5 121.27(18) . . ?
C14 C6 C5 116.0(2) . . ?
C14B C6 C5B 113.1(9) . . ?
C7 C6 C5B 117.1(7) . . ?
C6 C7 C11 120.45(13) . . ?
C6 C7 C8 122.13(13) . . ?
C11 C7 C8 117.36(12) . . ?
F10 C8 F9 104.99(11) . . ?
F10 C8 C7 110.42(12) . . ?
F9 C8 C7 110.98(13) . . ?
F10 C8 H8 110.1 . . ?
F9 C8 H8 110.1 . . ?
C7 C8 H8 110.1 . . ?
F13 C11 F12 104.86(12) . . ?
F13 C11 C7 110.05(13) . . ?
F12 C11 C7 112.33(13) . . ?
F13 C11 H11 109.8 . . ?
F12 C11 H11 109.8 . . ?
C7 C11 H11 109.8 . . ?
 
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
C5 S1 C2 C3 1.2(2) . . . . ?
S1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 -179.1(4) . . . . ?
C3 C4 C5 S1 2.0(3) . . . . ?
C2 S1 C5 C4 -1.8(2) . . . . ?
C2 S1 C5 C6 179.1(3) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C6 C14 C15 C16 -179.8(4) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C6 C14 C19 C18 179.8(4) . . . . ?
C5B S1B C2B C3B 2.6(11) . . . . ?
S1B C2B C3B C4B -3.1(15) . . . . ?
C2B C3B C4B C5B 2.0(17) . . . . ?
C3B C4B C5B C6 173.2(19) . . . . ?
C3B C4B C5B S1B -0.1(13) . . . . ?
C2B S1B C5B C4B -1.4(10) . . . . ?
C2B S1B C5B C6 -175.7(16) . . . . ?
C6 C14B C15B C16B 174.2(14) . . . . ?
C19B C14B C15B C16B 0.0 . . . . ?
C14B C15B C16B C17B 0.0 . . . . ?
C15B C16B C17B C18B 0.0 . . . . ?
C16B C17B C18B C19B 0.0 . . . . ?
C17B C18B C19B C14B 0.0 . . . . ?
C6 C14B C19B C18B -174.4(14) . . . . ?
C15B C14B C19B C18B 0.0 . . . . ?
C15B C14B C6 C7 -129.5(6) . . . . ?
C19B C14B C6 C7 44.8(13) . . . . ?
C15B C14B C6 C5B 47.7(13) . . . . ?
C19B C14B C6 C5B -138.0(10) . . . . ?
C15 C14 C6 C7 -121.67(19) . . . . ?
C19 C14 C6 C7 58.5(3) . . . . ?
C15 C14 C6 C5 57.7(3) . . . . ?
C19 C14 C6 C5 -122.1(3) . . . . ?
C4 C5 C6 C7 38.7(4) . . . . ?
S1 C5 C6 C7 -142.4(2) . . . . ?
C4 C5 C6 C14 -140.7(3) . . . . ?
S1 C5 C6 C14 38.2(4) . . . . ?
C4B C5B C6 C14B -120.5(17) . . . . ?
S1B C5B C6 C14B 51.9(17) . . . . ?
C4B C5B C6 C7 57.1(19) . . . . ?
S1B C5B C6 C7 -130.5(10) . . . . ?
C14B C6 C7 C11 -172.7(9) . . . . ?
C14 C6 C7 C11 9.0(3) . . . . ?
C5 C6 C7 C11 -170.3(2) . . . . ?
C5B C6 C7 C11 10.2(8) . . . . ?
C14B C6 C7 C8 4.6(9) . . . . ?
C14 C6 C7 C8 -173.7(2) . . . . ?
C5 C6 C7 C8 6.9(3) . . . . ?
C5B C6 C7 C8 -172.6(7) . . . . ?
C6 C7 C8 F10 145.96(14) . . . . ?
C11 C7 C8 F10 -36.71(18) . . . . ?
C6 C7 C8 F9 -98.05(16) . . . . ?
C11 C7 C8 F9 79.29(16) . . . . ?
C6 C7 C11 F13 136.47(14) . . . . ?
C8 C7 C11 F13 -40.90(17) . . . . ?
C6 C7 C11 F12 -107.10(16) . . . . ?
C8 C7 C11 F12 75.52(17) . . . . ?
 
_refine_diff_density_max    0.243
_refine_diff_density_min   -0.223
_refine_diff_density_rms    0.039



