# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_smba2bis_p21c
_database_code_depnum_ccdc_archive 'CCDC 1541512'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_audit_creation_date             2017-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2013-3
_chemical_name_systematic        
'2-fluoro-2-(phenylsulfonyl)thietane 1,1-dioxide'
_chemical_name_common            ?
_chemical_formula_moiety         'C9 H9 F O4 S2'
_chemical_formula_sum            'C9 H9 F O4 S2'
_chemical_formula_weight         264.28
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_diffrn_ambient_temperature      130.0
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.7355(6)
_cell_length_b                   9.6324(4)
_cell_length_c                   9.0837(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.2020(10)
_cell_angle_gamma                90
_cell_volume                     1089.15(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8490
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      30.112
_cell_measurement_theta_min      2.673
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.789
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.0700 before and 0.0291 after correction. 
The Ratio of minimum to maximum transmission is 0.7969. 
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12579
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.154
_diffrn_reflns_theta_min         2.674
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSMo'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2997
_reflns_number_total             3203
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2011.2-0'
_computing_data_collection       'APEX2 v2011.2-0'
_computing_data_reduction        'APEX2 v2011.2-0'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.5910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0887
_refine_special_details          
;
_olex2_refinement_description
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.30372(2) 0.38109(3) 0.86091(3) 0.01688(9) Uani 1 1 d . . . . .
S2 S 0.30223(2) 0.54428(3) 0.56171(3) 0.01683(9) Uani 1 1 d . . . . .
F1 F 0.40427(7) 0.62227(8) 0.82562(9) 0.02253(17) Uani 1 1 d . . . . .
O1 O 0.19304(8) 0.35299(12) 0.80097(13) 0.0276(2) Uani 1 1 d . . . . .
O2 O 0.33763(9) 0.42287(11) 1.01607(11) 0.0244(2) Uani 1 1 d . . . . .
O3 O 0.38020(8) 0.61767(11) 0.49771(12) 0.0240(2) Uani 1 1 d . . . . .
O4 O 0.25767(8) 0.41657(11) 0.49512(11) 0.0231(2) Uani 1 1 d . . . . .
C1 C 0.37199(9) 0.50093(13) 0.75202(13) 0.0161(2) Uani 1 1 d . . . . .
C2 C 0.46009(10) 0.39078(14) 0.75829(15) 0.0198(2) Uani 1 1 d . . . . .
H2A H 0.5259 0.4135 0.8340 0.024 Uiso 1 1 calc R . . . .
H2B H 0.4783 0.3757 0.6588 0.024 Uiso 1 1 calc R . . . .
C3 C 0.39842(11) 0.26601(14) 0.80709(15) 0.0201(2) Uani 1 1 d . . . . .
H3A H 0.4410 0.2126 0.8923 0.024 Uiso 1 1 calc R . . . .
H3B H 0.3666 0.2036 0.7229 0.024 Uiso 1 1 calc R . . . .
C4 C 0.20103(10) 0.65927(13) 0.58739(14) 0.0183(2) Uani 1 1 d . . . . .
C5 C 0.22383(11) 0.80079(15) 0.59570(18) 0.0263(3) Uani 1 1 d . . . . .
H5 H 0.2920 0.8339 0.5848 0.032 Uiso 1 1 calc R . . . .
C6 C 0.14547(12) 0.89247(15) 0.6202(2) 0.0316(3) Uani 1 1 d . . . . .
H6 H 0.1596 0.9894 0.6259 0.038 Uiso 1 1 calc R . . . .
C7 C 0.04643(12) 0.84251(16) 0.6362(2) 0.0300(3) Uani 1 1 d . . . . .
H7 H -0.0069 0.9057 0.6538 0.036 Uiso 1 1 calc R . . . .
C8 C 0.02413(11) 0.70095(16) 0.62702(19) 0.0286(3) Uani 1 1 d . . . . .
H8 H -0.0444 0.6682 0.6371 0.034 Uiso 1 1 calc R . . . .
C9 C 0.10186(11) 0.60740(14) 0.60308(17) 0.0231(3) Uani 1 1 d . . . . .
H9 H 0.0877 0.5105 0.5975 0.028 Uiso 1 1 calc R . . . .


_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 O1 1.4256(10) . ?
S1 O2 1.4414(10) . ?
S1 C1 1.8521(12) . ?
S1 C3 1.7809(13) . ?
S2 O3 1.4380(10) . ?
S2 O4 1.4339(11) . ?
S2 C1 1.8174(12) . ?
S2 C4 1.7519(13) . ?
F1 C1 1.3660(14) . ?
C1 C2 1.5366(17) . ?
C2 C3 1.5508(19) . ?
C4 C5 1.3925(19) . ?
C4 C9 1.3933(17) . ?
C5 C6 1.385(2) . ?
C6 C7 1.386(2) . ?
C7 C8 1.392(2) . ?
C8 C9 1.3893(19) . ?

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
O1 S1 O2 119.61(7) . . ?
O1 S1 C1 116.89(6) . . ?
O1 S1 C3 116.70(7) . . ?
O2 S1 C1 105.71(6) . . ?
O2 S1 C3 111.22(6) . . ?
C3 S1 C1 79.62(6) . . ?
O3 S2 C1 104.89(6) . . ?
O3 S2 C4 109.47(6) . . ?
O4 S2 O3 119.79(6) . . ?
O4 S2 C1 105.93(6) . . ?
O4 S2 C4 111.22(6) . . ?
C4 S2 C1 104.13(6) . . ?
S2 C1 S1 117.45(6) . . ?
F1 C1 S1 113.49(8) . . ?
F1 C1 S2 107.76(8) . . ?
F1 C1 C2 115.52(10) . . ?
C2 C1 S1 88.36(8) . . ?
C2 C1 S2 113.59(8) . . ?
C1 C2 C3 97.80(9) . . ?
C2 C3 S1 90.54(8) . . ?
C5 C4 S2 118.38(10) . . ?
C5 C4 C9 121.91(12) . . ?
C9 C4 S2 119.68(10) . . ?
C6 C5 C4 118.93(13) . . ?
C5 C6 C7 119.87(14) . . ?
C6 C7 C8 120.82(13) . . ?
C9 C8 C7 120.12(13) . . ?
C8 C9 C4 118.34(13) . . ?

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
S1 C1 C2 C3 15.34(9) . . . . ?
S2 C1 C2 C3 -104.04(10) . . . . ?
S2 C4 C5 C6 -178.23(13) . . . . ?
S2 C4 C9 C8 178.43(12) . . . . ?
F1 C1 C2 C3 130.69(11) . . . . ?
O1 S1 C1 S2 -12.33(10) . . . . ?
O1 S1 C1 F1 114.57(9) . . . . ?
O1 S1 C1 C2 -128.20(8) . . . . ?
O1 S1 C3 C2 128.28(8) . . . . ?
O2 S1 C1 S2 -148.24(7) . . . . ?
O2 S1 C1 F1 -21.33(10) . . . . ?
O2 S1 C1 C2 95.89(8) . . . . ?
O2 S1 C3 C2 -89.67(9) . . . . ?
O3 S2 C1 S1 -170.58(7) . . . . ?
O3 S2 C1 F1 59.78(9) . . . . ?
O3 S2 C1 C2 -69.53(10) . . . . ?
O3 S2 C4 C5 -21.52(14) . . . . ?
O3 S2 C4 C9 160.26(11) . . . . ?
O4 S2 C1 S1 -42.96(8) . . . . ?
O4 S2 C1 F1 -172.60(8) . . . . ?
O4 S2 C1 C2 58.09(10) . . . . ?
O4 S2 C4 C5 -156.15(11) . . . . ?
O4 S2 C4 C9 25.64(13) . . . . ?
C1 S1 C3 C2 13.29(7) . . . . ?
C1 S2 C4 C5 90.20(12) . . . . ?
C1 S2 C4 C9 -88.02(12) . . . . ?
C1 C2 C3 S1 -15.96(9) . . . . ?
C3 S1 C1 S2 102.45(8) . . . . ?
C3 S1 C1 F1 -130.64(10) . . . . ?
C3 S1 C1 C2 -13.42(8) . . . . ?
C4 S2 C1 S1 74.42(8) . . . . ?
C4 S2 C1 F1 -55.22(9) . . . . ?
C4 S2 C1 C2 175.47(9) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C4 C9 C8 0.3(2) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C7 C8 C9 C4 -0.6(2) . . . . ?
C9 C4 C5 C6 -0.1(2) . . . . ?

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration .

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_vipa_ba751_cmc21
_database_code_depnum_ccdc_archive 'CCDC 1541513'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_audit_creation_date             2017-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2013-3
_chemical_name_systematic        
'2,6-dibenzyltetrahydro-2H-thiopyran 1,1-dioxide'
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H22 O2 S'
_chemical_formula_sum            'C19 H22 O2 S'
_chemical_formula_weight         314.42
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'C m c 21'
_symmetry_int_tables_number      36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_diffrn_ambient_temperature      100.0
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'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   17.0370(10)
_cell_length_b                   10.9283(10)
_cell_length_c                   8.8054(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1639.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4517
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.203
_cell_measurement_theta_min      4.808
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.603
_exptl_absorpt_coefficient_mu    1.781
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.0984 before and 0.0417 after correction. 
The Ratio of minimum to maximum transmission is 0.6554. 
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.011
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6581
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_min         4.807
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSCu'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.869
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                1419
_reflns_number_total             1458
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2013.6-2'
_computing_data_collection       'APEX2 v2013.6-2'
_computing_data_reduction        'APEX2 v2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1458
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0636
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1482P)²+0.1158P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1719
_refine_special_details          
;
_olex2_refinement_description
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.5000 0.42460(10) 0.45796(14) 0.0362(5) Uani 1 2 d S T P . .
O1 O 0.5000 0.3564(4) 0.5984(5) 0.0419(9) Uani 1 2 d S T P . .
O2 O 0.5000 0.5561(3) 0.4695(7) 0.0468(11) Uani 1 2 d S T P . .
C1 C 0.5835(2) 0.3768(4) 0.3489(5) 0.0386(9) Uani 1 1 d . . . . .
H1 H 0.5862 0.4266 0.2537 0.046 Uiso 1 1 calc R . . . .
C2 C 0.5751(2) 0.2417(4) 0.3068(5) 0.0417(10) Uani 1 1 d . . . . .
H2A H 0.5757 0.1923 0.4011 0.050 Uiso 1 1 calc R . . . .
H2B H 0.6210 0.2170 0.2451 0.050 Uiso 1 1 calc R . . . .
C3 C 0.5000 0.2126(6) 0.2179(7) 0.0431(13) Uani 1 2 d S T P . .
H3A H 0.5000 0.2602 0.1223 0.052 Uiso 1 2 calc RS T P . .
H3B H 0.5000 0.1246 0.1908 0.052 Uiso 1 2 calc RS T P . .
C4 C 0.6556(2) 0.4060(4) 0.4487(6) 0.0398(9) Uani 1 1 d . . . . .
H4A H 0.6526 0.4927 0.4809 0.048 Uiso 1 1 calc R . . . .
H4B H 0.6533 0.3548 0.5413 0.048 Uiso 1 1 calc R . . . .
C5 C 0.7333(2) 0.3849(3) 0.3711(5) 0.0378(9) Uani 1 1 d . . . . .
C6 C 0.7607(2) 0.4656(3) 0.2613(5) 0.0406(10) Uani 1 1 d . . . . .
H6 H 0.7288 0.5328 0.2317 0.049 Uiso 1 1 calc R . . . .
C7 C 0.8332(3) 0.4506(4) 0.1943(6) 0.0467(11) Uani 1 1 d . . . . .
H7 H 0.8504 0.5058 0.1179 0.056 Uiso 1 1 calc R . . . .
C8 C 0.8808(2) 0.3547(4) 0.2390(6) 0.0493(11) Uani 1 1 d . . . . .
H8 H 0.9310 0.3442 0.1940 0.059 Uiso 1 1 calc R . . . .
C9 C 0.8551(2) 0.2734(4) 0.3500(7) 0.0525(12) Uani 1 1 d . . . . .
H9 H 0.8878 0.2077 0.3811 0.063 Uiso 1 1 calc R . . . .
C10 C 0.7822(3) 0.2884(4) 0.4148(6) 0.0470(11) Uani 1 1 d . . . . .
H10 H 0.7649 0.2324 0.4902 0.056 Uiso 1 1 calc R . . . .


_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 O1 1.444(4) . ?
S1 O2 1.441(4) . ?
S1 C1 1.794(4) 3_655 ?
S1 C1 1.794(4) . ?
C1 C2 1.528(6) . ?
C1 C4 1.544(5) . ?
C2 C3 1.534(5) . ?
C3 C2 1.534(5) 3_655 ?
C4 C5 1.507(6) . ?
C5 C6 1.390(6) . ?
C5 C10 1.398(6) . ?
C6 C7 1.378(6) . ?
C7 C8 1.382(7) . ?
C8 C9 1.391(7) . ?
C9 C10 1.376(7) . ?

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
O1 S1 C1 107.96(18) . 3_655 ?
O1 S1 C1 107.96(17) . . ?
O2 S1 O1 117.0(3) . . ?
O2 S1 C1 109.17(19) . 3_655 ?
O2 S1 C1 109.17(19) . . ?
C1 S1 C1 104.9(3) 3_655 . ?
C2 C1 S1 109.7(3) . . ?
C2 C1 C4 114.3(3) . . ?
C4 C1 S1 105.4(3) . . ?
C1 C2 C3 113.7(3) . . ?
C2 C3 C2 113.1(5) 3_655 . ?
C5 C4 C1 114.2(4) . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 C10 118.0(4) . . ?
C10 C5 C4 121.0(4) . . ?
C7 C6 C5 121.6(4) . . ?
C6 C7 C8 119.6(5) . . ?
C7 C8 C9 119.9(4) . . ?
C10 C9 C8 120.0(4) . . ?
C9 C10 C5 120.9(4) . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_vipabag1_p21
_database_code_depnum_ccdc_archive 'CCDC 1541515'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_audit_creation_date             2017-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2013-3
_chemical_name_systematic        
' (1,1-dioxido-2,4-thietanediyl)bis{[4-(trifluoromethyl)phenyl]}'
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H12 F6 O4 S'
_chemical_formula_sum            'C19 H12 F6 O4 S'
_chemical_formula_weight         450.35
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21'
_symmetry_int_tables_number      4
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_diffrn_ambient_temperature      100.0
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.8749(15)
_cell_length_b                   6.3714(12)
_cell_length_c                   15.789(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.698(6)
_cell_angle_gamma                90
_cell_volume                     888.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9683
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      31.542
_cell_measurement_theta_min      2.531
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.4748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.1467 before and 0.1013 after correction. 
The Ratio of minimum to maximum transmission is 0.6362. 
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.636
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.061
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            68662
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.736
_diffrn_reflns_theta_min         2.306
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSMo'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                5350
_reflns_number_total             5989
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2013.6-2'
_computing_data_collection       'APEX2 v2013.6-2'
_computing_data_reduction        'APEX2 v2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 2278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5989
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0741P)²+0.2431P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1203
_refine_special_details          
;
_olex2_refinement_description
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C14(H14), C15(H15), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.76858(6) 0.48142(9) 0.01564(4) 0.01417(13) Uani 1 1 d . . . . .
F1 F 0.7684(5) 0.7893(4) 0.44090(15) 0.0841(13) Uani 1 1 d . . . . .
F2 F 0.8560(2) 0.5217(4) 0.51148(11) 0.0348(5) Uani 1 1 d . . . . .
F3 F 0.6173(3) 0.5554(5) 0.48234(14) 0.0495(7) Uani 1 1 d . . . . .
F4 F 0.8888(2) 1.2689(3) -0.30990(13) 0.0351(4) Uani 1 1 d . . . . .
F5 F 0.8743(3) 1.0686(3) -0.41887(13) 0.0375(5) Uani 1 1 d . . . . .
F6 F 0.6757(2) 1.2265(3) -0.38410(16) 0.0406(5) Uani 1 1 d . . . . .
O1 O 0.9186(2) 0.5248(3) 0.05592(12) 0.0200(4) Uani 1 1 d . . . . .
O2 O 0.6582(2) 0.6471(3) 0.00738(12) 0.0193(4) Uani 1 1 d . . . . .
O3 O 0.8581(2) -0.0064(3) 0.12946(13) 0.0234(4) Uani 1 1 d . . . . .
O4 O 0.5414(3) 0.3193(4) -0.16887(15) 0.0340(5) Uani 1 1 d . . . . .
C1 C 0.6941(3) 0.2365(4) 0.05167(16) 0.0148(4) Uani 1 1 d . . . . .
H1 H 0.5828 0.2464 0.0565 0.018 Uiso 1 1 calc R . . . .
C2 C 0.7270(3) 0.1322(4) -0.03350(17) 0.0177(4) Uani 1 1 d . . . . .
H2A H 0.8099 0.0279 -0.0252 0.021 Uiso 1 1 calc R . . . .
H2B H 0.6357 0.0654 -0.0629 0.021 Uiso 1 1 calc R . . . .
C3 C 0.7750(3) 0.3303(4) -0.08116(16) 0.0163(4) Uani 1 1 d . . . . .
H3 H 0.8798 0.3186 -0.0989 0.020 Uiso 1 1 calc R . . . .
C4 C 0.7783(3) 0.1473(4) 0.13284(16) 0.0166(4) Uani 1 1 d . . . . .
C5 C 0.7624(3) 0.2575(4) 0.21502(16) 0.0171(4) Uani 1 1 d . . . . .
C6 C 0.6917(3) 0.4533(4) 0.21733(17) 0.0198(5) Uani 1 1 d . . . . .
H6 H 0.6445 0.5138 0.1664 0.024 Uiso 1 1 calc R . . . .
C7 C 0.6905(3) 0.5586(4) 0.29370(18) 0.0224(5) Uani 1 1 d . . . . .
H7 H 0.6446 0.6931 0.2951 0.027 Uiso 1 1 calc R . . . .
C8 C 0.7565(3) 0.4677(5) 0.36862(16) 0.0222(5) Uani 1 1 d . . . . .
C9 C 0.8241(4) 0.2706(4) 0.36753(18) 0.0245(6) Uani 1 1 d . . . . .
H9 H 0.8670 0.2079 0.4189 0.029 Uiso 1 1 calc R . . . .
C10 C 0.8279(3) 0.1662(4) 0.29014(18) 0.0216(5) Uani 1 1 d . . . . .
H10 H 0.8752 0.0327 0.2886 0.026 Uiso 1 1 calc R . . . .
C11 C 0.7502(4) 0.5841(5) 0.4506(2) 0.0328(7) Uani 1 1 d . . . . .
C12 C 0.6608(3) 0.4099(4) -0.15288(16) 0.0184(5) Uani 1 1 d . . . . .
C13 C 0.7002(3) 0.5981(4) -0.20186(16) 0.0162(4) Uani 1 1 d . . . . .
C14 C 0.8200(3) 0.7299(4) -0.17417(16) 0.0175(5) Uani 1 1 d . . . . .
H14 H 0.8796 0.7008 -0.1222 0.021 Uiso 1 1 calc R . . . .
C15 C 0.8531(3) 0.9042(4) -0.22206(17) 0.0181(5) Uani 1 1 d . . . . .
H15 H 0.9340 0.9953 -0.2027 0.022 Uiso 1 1 calc R . . . .
C16 C 0.7658(3) 0.9432(4) -0.29882(17) 0.0175(5) Uani 1 1 d . . . . .
C17 C 0.6469(3) 0.8108(4) -0.32762(17) 0.0207(5) Uani 1 1 d . . . . .
H17 H 0.5893 0.8375 -0.3805 0.025 Uiso 1 1 calc R . . . .
C18 C 0.6129(3) 0.6401(4) -0.27884(17) 0.0196(5) Uani 1 1 d . . . . .
H18 H 0.5303 0.5513 -0.2976 0.023 Uiso 1 1 calc R . . . .
C19 C 0.8020(3) 1.1266(4) -0.35287(18) 0.0224(5) 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 O1 1.4441(18) . ?
S1 O2 1.4369(19) . ?
S1 C1 1.808(2) . ?
S1 C3 1.812(3) . ?
F1 C11 1.328(4) . ?
F2 C11 1.336(4) . ?
F3 C11 1.339(5) . ?
F4 C19 1.331(3) . ?
F5 C19 1.329(3) . ?
F6 C19 1.340(3) . ?
O3 C4 1.213(3) . ?
O4 C12 1.212(3) . ?
C1 C2 1.554(4) . ?
C1 C4 1.528(4) . ?
C2 C3 1.550(4) . ?
C3 C12 1.529(3) . ?
C4 C5 1.494(4) . ?
C5 C6 1.399(3) . ?
C5 C10 1.395(4) . ?
C6 C7 1.381(4) . ?
C7 C8 1.393(4) . ?
C8 C9 1.393(4) . ?
C8 C11 1.497(4) . ?
C9 C10 1.395(4) . ?
C12 C13 1.487(4) . ?
C13 C14 1.390(3) . ?
C13 C18 1.401(4) . ?
C14 C15 1.391(4) . ?
C15 C16 1.394(4) . ?
C16 C17 1.392(4) . ?
C16 C19 1.500(4) . ?
C17 C18 1.383(4) . ?

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
O1 S1 C1 112.13(11) . . ?
O1 S1 C3 111.62(11) . . ?
O2 S1 O1 119.31(11) . . ?
O2 S1 C1 113.27(11) . . ?
O2 S1 C3 113.08(11) . . ?
C1 S1 C3 81.37(12) . . ?
C2 C1 S1 89.47(15) . . ?
C4 C1 S1 114.89(16) . . ?
C4 C1 C2 116.6(2) . . ?
C3 C2 C1 98.99(19) . . ?
C2 C3 S1 89.43(16) . . ?
C12 C3 S1 111.96(17) . . ?
C12 C3 C2 115.8(2) . . ?
O3 C4 C1 120.2(2) . . ?
O3 C4 C5 121.6(2) . . ?
C5 C4 C1 118.2(2) . . ?
C6 C5 C4 121.5(2) . . ?
C10 C5 C4 118.4(2) . . ?
C10 C5 C6 120.0(2) . . ?
C7 C6 C5 119.9(2) . . ?
C6 C7 C8 120.0(3) . . ?
C7 C8 C11 118.6(3) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 C11 120.7(2) . . ?
C8 C9 C10 119.3(2) . . ?
C9 C10 C5 120.1(2) . . ?
F1 C11 F2 106.9(3) . . ?
F1 C11 F3 107.4(4) . . ?
F1 C11 C8 111.9(3) . . ?
F2 C11 F3 105.8(3) . . ?
F2 C11 C8 113.0(3) . . ?
F3 C11 C8 111.5(3) . . ?
O4 C12 C3 119.9(2) . . ?
O4 C12 C13 121.5(2) . . ?
C13 C12 C3 118.7(2) . . ?
C14 C13 C12 122.4(2) . . ?
C14 C13 C18 119.8(2) . . ?
C18 C13 C12 117.8(2) . . ?
C13 C14 C15 120.5(2) . . ?
C14 C15 C16 119.1(2) . . ?
C15 C16 C19 120.1(2) . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 C19 119.0(2) . . ?
C18 C17 C16 119.7(2) . . ?
C17 C18 C13 120.1(2) . . ?
F4 C19 F6 106.5(2) . . ?
F4 C19 C16 112.7(2) . . ?
F5 C19 F4 106.8(3) . . ?
F5 C19 F6 107.1(2) . . ?
F5 C19 C16 112.1(2) . . ?
F6 C19 C16 111.2(2) . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vipabag1_p21n
_database_code_depnum_ccdc_archive 'CCDC 1541514'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_audit_creation_date             2017-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2013-3
_chemical_name_systematic        
(1,1-dioxido-2,4-thietanediyl)bis{[4-(trifluoromethyl)phenyl]}
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H12 F6 O4 S'
_chemical_formula_sum            'C19 H12 F6 O4 S'
_chemical_formula_weight         450.35
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_diffrn_ambient_temperature      130.0
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.9602(6)
_cell_length_b                   31.951(3)
_cell_length_c                   8.3374(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.572(4)
_cell_angle_gamma                90
_cell_volume                     1802.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9477
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      30.023
_cell_measurement_theta_min      2.550
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.890
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.0938 before and 0.0473 after correction. 
The Ratio of minimum to maximum transmission is 0.9162. 
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.37
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            64267
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.160
_diffrn_reflns_theta_min         1.275
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSMo'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4783
_reflns_number_total             5306
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2011.2-0'
_computing_data_collection       'APEX2 v2011.2-0'
_computing_data_reduction        'APEX2 v2011.2-0'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²+1.7882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          
;
_olex2_refinement_description
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C14(H14), C15(H15), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.85192(5) 0.22886(2) 0.02759(5) 0.01776(10) Uani 1 1 d . . . . .
F1 F 1.2439(2) 0.02022(5) -0.1263(2) 0.0652(5) Uani 1 1 d . . . . .
F2 F 1.0874(4) 0.03616(6) -0.3670(2) 0.0789(7) Uani 1 1 d . . . . .
F3 F 0.9749(2) -0.01017(4) -0.2316(3) 0.0636(5) Uani 1 1 d . . . . .
F4 F 1.25234(19) 0.42097(4) -0.1705(2) 0.0476(4) Uani 1 1 d . . . . .
F5 F 0.9734(2) 0.44564(5) -0.29554(18) 0.0495(4) Uani 1 1 d . . . . .
F6 F 1.1048(3) 0.46651(4) -0.0538(2) 0.0569(4) Uani 1 1 d . . . . .
O1 O 0.72168(19) 0.23301(4) -0.13330(15) 0.0280(3) Uani 1 1 d . . . . .
O2 O 1.06030(17) 0.22771(4) 0.04074(16) 0.0240(2) Uani 1 1 d . . . . .
O3 O 0.4609(2) 0.15419(5) 0.0124(3) 0.0487(5) Uani 1 1 d . . . . .
O4 O 0.4763(2) 0.30270(5) 0.0665(2) 0.0414(4) Uani 1 1 d . . . . .
C1 C 0.7539(2) 0.18969(5) 0.1433(2) 0.0210(3) Uani 1 1 d . . . . .
H1 H 0.8603 0.1781 0.2347 0.025 Uiso 1 1 calc R . . . .
C2 C 0.6377(3) 0.22468(5) 0.2076(2) 0.0234(3) Uani 1 1 d . . . . .
H2A H 0.6429 0.2217 0.3268 0.028 Uiso 1 1 calc R . . . .
H2B H 0.4985 0.2263 0.1444 0.028 Uiso 1 1 calc R . . . .
C3 C 0.7626(2) 0.26203(5) 0.1713(2) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.8707 0.2692 0.2695 0.023 Uiso 1 1 calc R . . . .
C4 C 0.6396(3) 0.15474(5) 0.0399(2) 0.0265(3) Uani 1 1 d . . . . .
C5 C 0.7534(2) 0.12235(5) -0.0270(2) 0.0228(3) Uani 1 1 d . . . . .
C6 C 0.9563(3) 0.12560(5) -0.0125(3) 0.0277(4) Uani 1 1 d . . . . .
H6 H 1.0266 0.1491 0.0413 0.033 Uiso 1 1 calc R . . . .
C7 C 1.0559(3) 0.09457(6) -0.0765(3) 0.0296(4) Uani 1 1 d . . . . .
H7 H 1.1939 0.0971 -0.0687 0.036 Uiso 1 1 calc R . . . .
C8 C 0.9533(3) 0.05989(5) -0.1520(2) 0.0242(3) Uani 1 1 d . . . . .
C9 C 0.7515(3) 0.05619(6) -0.1665(2) 0.0279(4) Uani 1 1 d . . . . .
H9 H 0.6821 0.0323 -0.2179 0.033 Uiso 1 1 calc R . . . .
C10 C 0.6526(3) 0.08756(6) -0.1055(2) 0.0278(4) Uani 1 1 d . . . . .
H10 H 0.5139 0.0854 -0.1172 0.033 Uiso 1 1 calc R . . . .
C11 C 1.0640(3) 0.02664(6) -0.2198(3) 0.0306(4) Uani 1 1 d . . . . .
C12 C 0.6550(2) 0.30082(5) 0.0931(2) 0.0240(3) Uani 1 1 d . . . . .
C13 C 0.7736(2) 0.33516(5) 0.0423(2) 0.0213(3) Uani 1 1 d . . . . .
C14 C 0.9777(2) 0.33268(5) 0.0615(2) 0.0215(3) Uani 1 1 d . . . . .
H14 H 1.0487 0.3094 0.1163 0.026 Uiso 1 1 calc R . . . .
C15 C 1.0770(2) 0.36436(5) 0.0003(2) 0.0231(3) Uani 1 1 d . . . . .
H15 H 1.2161 0.3627 0.0129 0.028 Uiso 1 1 calc R . . . .
C16 C 0.9729(2) 0.39841(5) -0.0791(2) 0.0221(3) Uani 1 1 d . . . . .
C17 C 0.7704(3) 0.40177(6) -0.0951(3) 0.0295(4) Uani 1 1 d . . . . .
H17 H 0.7003 0.4255 -0.1471 0.035 Uiso 1 1 calc R . . . .
C18 C 0.6722(3) 0.37020(6) -0.0343(3) 0.0299(4) Uani 1 1 d . . . . .
H18 H 0.5336 0.3723 -0.0448 0.036 Uiso 1 1 calc R . . . .
C19 C 1.0767(3) 0.43263(5) -0.1482(2) 0.0273(3) 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 O1 1.4380(13) . ?
S1 O2 1.4291(12) . ?
S1 C1 1.8089(16) . ?
S1 C3 1.8149(16) . ?
F1 C11 1.326(2) . ?
F2 C11 1.311(3) . ?
F3 C11 1.322(2) . ?
F4 C19 1.332(2) . ?
F5 C19 1.336(2) . ?
F6 C19 1.326(2) . ?
O3 C4 1.211(2) . ?
O4 C12 1.213(2) . ?
C1 C2 1.547(2) . ?
C1 C4 1.517(2) . ?
C2 C3 1.548(2) . ?
C3 C12 1.514(2) . ?
C4 C5 1.489(2) . ?
C5 C6 1.393(2) . ?
C5 C10 1.393(2) . ?
C6 C7 1.386(2) . ?
C7 C8 1.387(2) . ?
C8 C9 1.387(2) . ?
C8 C11 1.498(2) . ?
C9 C10 1.379(2) . ?
C12 C13 1.493(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.396(2) . ?
C14 C15 1.389(2) . ?
C15 C16 1.387(2) . ?
C16 C17 1.389(2) . ?
C16 C19 1.498(2) . ?
C17 C18 1.380(3) . ?

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
O1 S1 C1 109.10(8) . . ?
O1 S1 C3 108.87(8) . . ?
O2 S1 O1 118.70(8) . . ?
O2 S1 C1 116.37(8) . . ?
O2 S1 C3 117.59(7) . . ?
C1 S1 C3 79.71(7) . . ?
C2 C1 S1 88.74(10) . . ?
C4 C1 S1 114.77(12) . . ?
C4 C1 C2 118.79(14) . . ?
C1 C2 C3 97.24(12) . . ?
C2 C3 S1 88.52(10) . . ?
C12 C3 S1 113.91(12) . . ?
C12 C3 C2 118.15(14) . . ?
O3 C4 C1 119.77(16) . . ?
O3 C4 C5 122.17(16) . . ?
C5 C4 C1 118.05(14) . . ?
C6 C5 C4 122.24(15) . . ?
C10 C5 C4 118.50(15) . . ?
C10 C5 C6 119.26(15) . . ?
C7 C6 C5 120.13(16) . . ?
C6 C7 C8 119.69(16) . . ?
C7 C8 C11 118.83(16) . . ?
C9 C8 C7 120.73(16) . . ?
C9 C8 C11 120.43(16) . . ?
C10 C9 C8 119.28(16) . . ?
C9 C10 C5 120.89(16) . . ?
F1 C11 C8 112.70(16) . . ?
F2 C11 F1 106.2(2) . . ?
F2 C11 F3 107.21(19) . . ?
F2 C11 C8 112.11(17) . . ?
F3 C11 F1 105.51(18) . . ?
F3 C11 C8 112.64(16) . . ?
O4 C12 C3 120.09(15) . . ?
O4 C12 C13 121.58(15) . . ?
C13 C12 C3 118.25(14) . . ?
C14 C13 C12 122.81(14) . . ?
C14 C13 C18 119.38(15) . . ?
C18 C13 C12 117.74(15) . . ?
C15 C14 C13 119.88(15) . . ?
C16 C15 C14 119.85(15) . . ?
C15 C16 C17 120.76(15) . . ?
C15 C16 C19 120.72(15) . . ?
C17 C16 C19 118.52(15) . . ?
C18 C17 C16 119.19(15) . . ?
C17 C18 C13 120.89(16) . . ?
F4 C19 F5 105.83(16) . . ?
F4 C19 C16 113.01(14) . . ?
F5 C19 C16 112.10(16) . . ?
F6 C19 F4 107.40(17) . . ?
F6 C19 F5 105.35(16) . . ?
F6 C19 C16 112.61(16) . . ?

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration .

