 
data_A25208O_004
 
_audit_creation_method            'SHELXL-2019/3'
_shelx_SHELXL_version_number      '2019/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C15 H12 F4 O S'
_chemical_formula_sum
 'C15 H12 F4 O S' 
_chemical_formula_weight          316.31

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'
 '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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'
 
_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'
 
_cell_length_a                    7.9666(8)
_cell_length_b                    5.5479(6)
_cell_length_c                    15.6652(16)
_cell_angle_alpha                 90
_cell_angle_beta                  102.364(3)
_cell_angle_gamma                 90
_cell_volume                      676.31(12)
_cell_formula_units_Z             2
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     6772
_cell_measurement_theta_min       2.66
_cell_measurement_theta_max       26.00
 
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.553          
_exptl_crystal_F_000              324
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.114
_exptl_crystal_size_mid           0.071
_exptl_crystal_size_min           0.023
_exptl_absorpt_coefficient_mu     0.281
_shelx_estimated_absorpt_T_min    0.969
_shelx_estimated_absorpt_T_max    0.994
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.7156
_exptl_absorpt_correction_T_max   0.7453
_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 CPAD detector'
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             8442
_diffrn_reflns_av_unetI/netI      0.0630
_diffrn_reflns_av_R_equivalents   0.0885
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          2.617
_diffrn_reflns_theta_max          26.004
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.980
_diffrn_measured_fraction_theta_full  0.981
_diffrn_reflns_Laue_measured_fraction_max    0.980
_diffrn_reflns_Laue_measured_fraction_full   0.981
_diffrn_reflns_point_group_measured_fraction_max   0.962
_diffrn_reflns_point_group_measured_fraction_full  0.967
_reflns_number_total              2549
_reflns_number_gt                 2336
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.770
_reflns_Friedel_fraction_max      0.940
_reflns_Friedel_fraction_full     0.950
 
_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)+(0.0272P)²+0.0871P] 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_abs_structure_details
;
 Flack x determined using 920 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.08(4)
_chemical_absolute_configuration  .
_refine_ls_number_reflns          2549
_refine_ls_number_parameters      191
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0395
_refine_ls_R_factor_gt            0.0287
_refine_ls_wR_factor_ref          0.0740
_refine_ls_wR_factor_gt           0.0708
_refine_ls_goodness_of_fit_ref    1.082
_refine_ls_restrained_S_all       1.082
_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 0.96137(9) 0.72811(16) 0.81053(4) 0.03272(17) Uani 1 1 d . . . . .
C2 C 1.0114(4) 0.9454(6) 0.88837(19) 0.0361(7) Uani 1 1 d . . . . .
H2 H 1.118365 1.027738 0.901352 0.043 Uiso 1 1 calc R U . . .
C3 C 0.8820(4) 0.9876(6) 0.92962(19) 0.0361(7) Uani 1 1 d . . . . .
H3 H 0.887962 1.103290 0.974894 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7370(4) 0.8418(5) 0.89834(18) 0.0281(6) Uani 1 1 d . . . . .
H4 H 0.634771 0.848859 0.920224 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7596(3) 0.6867(5) 0.83220(15) 0.0229(6) Uani 1 1 d . . . . .
C6 C 0.6400(3) 0.5183(5) 0.77818(16) 0.0219(5) Uani 1 1 d . . . . .
C7 C 0.5122(3) 0.3994(5) 0.80427(16) 0.0235(5) Uani 1 1 d . . . . .
C8 C 0.4883(4) 0.4151(6) 0.89657(17) 0.0260(6) Uani 1 1 d . . . . .
H8 H 0.601113 0.443639 0.937658 0.031 Uiso 1 1 calc R U . . .
F9 F 0.3734(2) 0.5959(4) 0.90481(11) 0.0377(4) Uani 1 1 d . . . . .
F10 F 0.4138(2) 0.2088(4) 0.91895(10) 0.0375(4) Uani 1 1 d . . . . .
C11 C 0.3864(3) 0.2507(6) 0.74107(16) 0.0262(6) Uani 1 1 d . . . . .
H11 H 0.400559 0.282980 0.680206 0.031 Uiso 1 1 calc R U . . .
F12 F 0.4062(3) 0.0090(4) 0.75867(12) 0.0403(4) Uani 1 1 d . . . . .
F13 F 0.2226(2) 0.3027(4) 0.74724(12) 0.0413(5) Uani 1 1 d . . . . .
C14 C 0.6707(3) 0.4868(5) 0.68740(15) 0.0214(5) Uani 1 1 d . . . . .
C15 C 0.6158(3) 0.6647(5) 0.62442(16) 0.0234(5) Uani 1 1 d . . . . .
H15 H 0.554560 0.800790 0.638434 0.028 Uiso 1 1 calc R U . . .
C16 C 0.6501(3) 0.6439(5) 0.54203(16) 0.0235(5) Uani 1 1 d . . . . .
H16 H 0.610200 0.764226 0.499333 0.028 Uiso 1 1 calc R U . . .
C17 C 0.7424(3) 0.4483(5) 0.52109(16) 0.0214(5) Uani 1 1 d . . . . .
C18 C 0.7991(3) 0.2711(5) 0.58309(16) 0.0265(6) Uani 1 1 d . . . . .
H18 H 0.863351 0.137674 0.569474 0.032 Uiso 1 1 calc R U . . .
C19 C 0.7607(4) 0.2909(5) 0.66561(18) 0.0284(6) Uani 1 1 d . . . . .
H19 H 0.796899 0.167701 0.707617 0.034 Uiso 1 1 calc R U . . .
O20 O 0.7713(3) 0.4501(4) 0.43804(11) 0.0278(4) Uani 1 1 d . . . . .
C21 C 0.8582(4) 0.2470(7) 0.41184(18) 0.0365(7) Uani 1 1 d . . . . .
H21A H 0.865451 0.265439 0.350510 0.055 Uiso 1 1 calc R U . . .
H21B H 0.794571 0.099574 0.418594 0.055 Uiso 1 1 calc R U . . .
H21C H 0.974341 0.236637 0.448427 0.055 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 C2 1.700(3) . ?
S1 C5 1.728(3) . ?
C2 C3 1.349(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.467(4) . ?
C6 C7 1.348(4) . ?
C6 C14 1.504(3) . ?
C7 C11 1.497(4) . ?
C7 C8 1.501(3) . ?
C8 F10 1.369(3) . ?
C8 F9 1.382(3) . ?
C8 H8 1.0000 . ?
C11 F13 1.360(3) . ?
C11 F12 1.371(4) . ?
C11 H11 1.0000 . ?
C14 C19 1.384(4) . ?
C14 C15 1.398(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C17 O20 1.369(3) . ?
C17 C18 1.388(4) . ?
C18 C19 1.395(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O20 C21 1.428(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
 
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 92.19(15) . . ?
C3 C2 S1 112.4(2) . . ?
C3 C2 H2 123.8 . . ?
S1 C2 H2 123.8 . . ?
C2 C3 C4 112.8(3) . . ?
C2 C3 H3 123.6 . . ?
C4 C3 H3 123.6 . . ?
C5 C4 C3 112.8(3) . . ?
C5 C4 H4 123.6 . . ?
C3 C4 H4 123.6 . . ?
C4 C5 C6 130.8(2) . . ?
C4 C5 S1 109.8(2) . . ?
C6 C5 S1 119.19(18) . . ?
C7 C6 C5 125.2(2) . . ?
C7 C6 C14 121.1(2) . . ?
C5 C6 C14 113.7(2) . . ?
C6 C7 C11 120.8(2) . . ?
C6 C7 C8 121.6(3) . . ?
C11 C7 C8 117.6(2) . . ?
F10 C8 F9 104.5(2) . . ?
F10 C8 C7 110.5(2) . . ?
F9 C8 C7 110.8(2) . . ?
F10 C8 H8 110.3 . . ?
F9 C8 H8 110.3 . . ?
C7 C8 H8 110.3 . . ?
F13 C11 F12 105.3(2) . . ?
F13 C11 C7 110.7(2) . . ?
F12 C11 C7 112.0(2) . . ?
F13 C11 H11 109.6 . . ?
F12 C11 H11 109.6 . . ?
C7 C11 H11 109.6 . . ?
C19 C14 C15 118.7(2) . . ?
C19 C14 C6 121.5(2) . . ?
C15 C14 C6 119.7(2) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
O20 C17 C18 125.1(2) . . ?
O20 C17 C16 115.1(2) . . ?
C18 C17 C16 119.8(2) . . ?
C17 C18 C19 119.3(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C14 C19 C18 121.2(2) . . ?
C14 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C17 O20 C21 117.3(2) . . ?
O20 C21 H21A 109.5 . . ?
O20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C5 S1 C2 C3 -0.1(3) . . . . ?
S1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -175.5(3) . . . . ?
C3 C4 C5 S1 -0.2(3) . . . . ?
C2 S1 C5 C4 0.2(2) . . . . ?
C2 S1 C5 C6 176.1(2) . . . . ?
C4 C5 C6 C7 -31.6(5) . . . . ?
S1 C5 C6 C7 153.5(2) . . . . ?
C4 C5 C6 C14 148.1(3) . . . . ?
S1 C5 C6 C14 -26.8(3) . . . . ?
C5 C6 C7 C11 173.8(3) . . . . ?
C14 C6 C7 C11 -5.9(4) . . . . ?
C5 C6 C7 C8 -4.9(4) . . . . ?
C14 C6 C7 C8 175.4(3) . . . . ?
C6 C7 C8 F10 -151.4(3) . . . . ?
C11 C7 C8 F10 29.9(4) . . . . ?
C6 C7 C8 F9 93.3(3) . . . . ?
C11 C7 C8 F9 -85.4(3) . . . . ?
C6 C7 C11 F13 -131.8(3) . . . . ?
C8 C7 C11 F13 46.9(3) . . . . ?
C6 C7 C11 F12 111.0(3) . . . . ?
C8 C7 C11 F12 -70.2(3) . . . . ?
C7 C6 C14 C19 -81.0(4) . . . . ?
C5 C6 C14 C19 99.3(3) . . . . ?
C7 C6 C14 C15 102.5(3) . . . . ?
C5 C6 C14 C15 -77.2(3) . . . . ?
C19 C14 C15 C16 0.4(4) . . . . ?
C6 C14 C15 C16 177.0(3) . . . . ?
C14 C15 C16 C17 -1.3(4) . . . . ?
C15 C16 C17 O20 -178.7(2) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
O20 C17 C18 C19 -180.0(3) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C15 C14 C19 C18 1.0(4) . . . . ?
C6 C14 C19 C18 -175.5(3) . . . . ?
C17 C18 C19 C14 -1.6(4) . . . . ?
C18 C17 O20 C21 3.6(4) . . . . ?
C16 C17 O20 C21 -177.0(3) . . . . ?
 
_refine_diff_density_max    0.204
_refine_diff_density_min   -0.163
_refine_diff_density_rms    0.042



