# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1586321'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_vrf_RINTA01_shelx               
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.207 
RESPONSE: Regardless the crystallization method the samples of this
compound has found to be always twinned and not so great quality.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 F3 N O3 S'
_chemical_formula_sum            'C13 H8 F3 N O3 S'
_chemical_formula_weight         315.26

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'
N N 0.0311 0.0180 '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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   4.7875(4)
_cell_length_b                   10.5072(9)
_cell_length_c                   14.2488(15)
_cell_angle_alpha                71.680(9)
_cell_angle_beta                 88.646(8)
_cell_angle_gamma                76.869(7)
_cell_volume                     661.76(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    175
_cell_measurement_theta_min      9.5070
_cell_measurement_theta_max      63.4460

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.567
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    2.636
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            4295
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.2070
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         66.691
_diffrn_reflns_theta_full        66.691
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4295
_reflns_number_gt                3270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SuperFlip (Palatinus & Chapius, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component perfect twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0651P)²+0.9632P] 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         4295
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.1180
_refine_ls_wR_factor_ref         0.2653
_refine_ls_wR_factor_gt          0.2534
_refine_ls_goodness_of_fit_ref   1.334
_refine_ls_restrained_S_all      1.334
_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 0.9052(4) 0.1514(2) 0.08744(14) 0.0411(5) Uani 1 1 d . . . . .
F1 F 0.7970(13) 0.2494(7) -0.0978(4) 0.0767(17) Uani 1 1 d . . . . .
F2 F 0.4526(10) 0.3261(7) -0.0172(4) 0.0708(17) Uani 1 1 d . . . . .
F3 F 0.8243(12) 0.4071(6) -0.0368(4) 0.0647(15) Uani 1 1 d . . . . .
O1 O 0.2602(15) 0.0139(7) 0.4130(5) 0.0609(18) Uani 1 1 d . . . . .
O2 O 0.3476(16) 0.5192(6) 0.3871(5) 0.0649(18) Uani 1 1 d . . . . .
N1 N 0.5681(11) 0.0134(6) 0.2539(4) 0.0293(12) Uani 1 1 d . . . . .
H1 H 0.3988 -0.0011 0.2524 0.035 Uiso 1 1 calc R U . . .
O3 O 1.0413(10) -0.0778(6) 0.2535(4) 0.0432(13) Uani 1 1 d . . . . .
C6 C 0.7533(14) 0.2188(7) 0.1825(5) 0.0315(15) Uani 1 1 d . . . . .
C7 C 0.7870(17) 0.3459(8) 0.1844(6) 0.0416(18) Uani 1 1 d . . . . .
H2 H 0.9034 0.3920 0.1396 0.050 Uiso 1 1 calc R U . . .
C8A C 0.4810(16) 0.3351(7) 0.3204(5) 0.0355(16) Uani 1 1 d . . . . .
C10 C 0.7962(14) -0.0914(7) 0.2563(5) 0.0304(15) Uani 1 1 d . . . . .
C3 C 0.1465(18) 0.2003(9) 0.4718(6) 0.046(2) Uani 1 1 d . . . . .
H5 H 0.0413 0.1543 0.5213 0.055 Uiso 1 1 calc R U . . .
C4A C 0.4565(14) 0.2030(7) 0.3235(5) 0.0310(15) Uani 1 1 d . . . . .
C4 C 0.2858(15) 0.1297(8) 0.4030(5) 0.0365(16) Uani 1 1 d . . . . .
C1 C 0.3323(18) 0.4032(8) 0.3918(6) 0.0443(19) Uani 1 1 d . . . . .
C2 C 0.163(2) 0.3260(9) 0.4667(6) 0.051(2) Uani 1 1 d . . . . .
H9 H 0.0670 0.3664 0.5114 0.062 Uiso 1 1 calc R U . . .
C9 C 0.7346(17) 0.2912(10) -0.0191(6) 0.047(2) Uani 1 1 d . . . . .
C8 C 0.6499(17) 0.4041(8) 0.2520(6) 0.0426(18) Uani 1 1 d . . . . .
H11 H 0.6708 0.4900 0.2517 0.051 Uiso 1 1 calc R U . . .
C5 C 0.5923(13) 0.1441(7) 0.2537(5) 0.0284(14) Uani 1 1 d . . . . .
C11 C 0.7230(16) -0.2244(8) 0.2606(7) 0.0415(18) Uani 1 1 d . . . . .
H13A H 0.5186 -0.2138 0.2623 0.062 Uiso 0.5 1 calc R U P . .
H13B H 0.7897 -0.2490 0.2032 0.062 Uiso 0.5 1 calc R U P . .
H13C H 0.8140 -0.2957 0.3191 0.062 Uiso 0.5 1 calc R U P . .
H13D H 0.8962 -0.2918 0.2607 0.062 Uiso 0.5 1 calc R U P . .
H13E H 0.6252 -0.2566 0.3199 0.062 Uiso 0.5 1 calc R U P . .
H13F H 0.6009 -0.2100 0.2040 0.062 Uiso 0.5 1 calc R U P . .


_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 C6 1.786(7) . ?
S1 C9 1.800(9) . ?
F1 C9 1.332(10) . ?
F2 C9 1.318(9) . ?
F3 C9 1.331(10) . ?
O1 C4 1.214(9) . ?
O2 C1 1.219(9) . ?
N1 C10 1.355(9) . ?
N1 C5 1.403(8) . ?
N1 H1 0.8600 . ?
O3 C10 1.212(8) . ?
C6 C7 1.390(10) . ?
C6 C5 1.406(9) . ?
C7 C8 1.374(11) . ?
C7 H2 0.9300 . ?
C8A C8 1.383(11) . ?
C8A C4A 1.406(10) . ?
C8A C1 1.498(11) . ?
C10 C11 1.499(10) . ?
C3 C2 1.320(12) . ?
C3 C4 1.469(11) . ?
C3 H5 0.9300 . ?
C4A C5 1.404(10) . ?
C4A C4 1.495(10) . ?
C1 C2 1.471(12) . ?
C2 H9 0.9300 . ?
C8 H11 0.9300 . ?
C11 H13A 0.9600 . ?
C11 H13B 0.9600 . ?
C11 H13C 0.9600 . ?
C11 H13D 0.9600 . ?
C11 H13E 0.9600 . ?
C11 H13F 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
C6 S1 C9 99.1(4) . . ?
C10 N1 C5 123.8(5) . . ?
C10 N1 H1 118.1 . . ?
C5 N1 H1 118.1 . . ?
C7 C6 C5 120.3(7) . . ?
C7 C6 S1 120.3(5) . . ?
C5 C6 S1 119.4(5) . . ?
C8 C7 C6 120.6(7) . . ?
C8 C7 H2 119.7 . . ?
C6 C7 H2 119.7 . . ?
C8 C8A C4A 120.3(7) . . ?
C8 C8A C1 118.4(7) . . ?
C4A C8A C1 121.3(7) . . ?
O3 C10 N1 122.4(6) . . ?
O3 C10 C11 122.4(7) . . ?
N1 C10 C11 115.2(6) . . ?
C2 C3 C4 123.2(8) . . ?
C2 C3 H5 118.4 . . ?
C4 C3 H5 118.4 . . ?
C8A C4A C5 119.7(6) . . ?
C8A C4A C4 118.0(6) . . ?
C5 C4A C4 122.3(6) . . ?
O1 C4 C3 118.9(7) . . ?
O1 C4 C4A 122.4(7) . . ?
C3 C4 C4A 118.6(7) . . ?
O2 C1 C2 121.1(7) . . ?
O2 C1 C8A 121.1(8) . . ?
C2 C1 C8A 117.7(7) . . ?
C3 C2 C1 121.2(7) . . ?
C3 C2 H9 119.4 . . ?
C1 C2 H9 119.4 . . ?
F2 C9 F1 107.6(7) . . ?
F2 C9 F3 106.2(8) . . ?
F1 C9 F3 106.1(6) . . ?
F2 C9 S1 114.1(5) . . ?
F1 C9 S1 106.9(6) . . ?
F3 C9 S1 115.5(6) . . ?
C7 C8 C8A 120.2(7) . . ?
C7 C8 H11 119.9 . . ?
C8A C8 H11 119.9 . . ?
C6 C5 N1 120.1(6) . . ?
C6 C5 C4A 118.8(6) . . ?
N1 C5 C4A 121.1(6) . . ?
C10 C11 H13A 109.5 . . ?
C10 C11 H13B 109.5 . . ?
H13A C11 H13B 109.5 . . ?
C10 C11 H13C 109.5 . . ?
H13A C11 H13C 109.5 . . ?
H13B C11 H13C 109.5 . . ?
C10 C11 H13D 109.5 . . ?
H13A C11 H13D 141.1 . . ?
H13B C11 H13D 56.3 . . ?
H13C C11 H13D 56.3 . . ?
C10 C11 H13E 109.5 . . ?
H13A C11 H13E 56.3 . . ?
H13B C11 H13E 141.1 . . ?
H13C C11 H13E 56.3 . . ?
H13D C11 H13E 109.5 . . ?
C10 C11 H13F 109.5 . . ?
H13A C11 H13F 56.3 . . ?
H13B C11 H13F 56.3 . . ?
H13C C11 H13F 141.1 . . ?
H13D C11 H13F 109.5 . . ?
H13E C11 H13F 109.5 . . ?

_refine_diff_density_max         0.958
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1586748'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H7 F3 O4 S'
_chemical_formula_sum            'C15 H7 F3 O4 S'
_chemical_formula_weight         340.27

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'
F F 0.0727 0.0534 '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                   12.2391(3)
_cell_length_b                   8.0497(2)
_cell_length_c                   13.6415(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.602(2)
_cell_angle_gamma                90
_cell_volume                     1343.45(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4638
_cell_measurement_theta_min      3.5830
_cell_measurement_theta_max      67.2850

_exptl_crystal_description       block
_exptl_crystal_density_meas      yellow
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.129
_exptl_absorpt_coefficient_mu    2.690
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_T_max  0.757
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            11565
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.613
_diffrn_reflns_theta_max         67.190
_diffrn_reflns_theta_full        67.190
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2405
_reflns_number_gt                2051
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SuperFlip (Palatinus & Chapius, 2007)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1238P)²+0.7476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0103(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2405
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.1861
_refine_ls_wR_factor_gt          0.1733
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_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 0.61764(6) 0.69479(8) 0.17362(6) 0.0379(3) Uani 1 1 d . . . . .
O3 O 0.6656(2) 0.8245(3) 0.2314(2) 0.0522(7) Uani 1 1 d . . . . .
F3 F 0.6244(2) 0.9282(3) 0.0347(2) 0.0682(7) Uani 1 1 d . . . . .
O1 O 0.82297(19) 0.8075(2) 0.0947(2) 0.0469(7) Uani 1 1 d . . . . .
O4 O 0.5132(2) 0.6310(3) 0.1988(3) 0.0666(9) Uani 1 1 d . . . . .
F2 F 0.4862(2) 0.7724(4) 0.0240(3) 0.0868(10) Uani 1 1 d . . . . .
O2 O 1.0509(2) 0.2480(3) 0.14963(19) 0.0502(7) Uani 1 1 d . . . . .
F1 F 0.6399(3) 0.6821(4) -0.02019(19) 0.0798(9) Uani 1 1 d . . . . .
C9A C 0.8198(2) 0.5285(3) 0.14579(18) 0.0265(6) Uani 1 1 d . . . . .
C11 C 0.5913(3) 0.7745(4) 0.0450(3) 0.0481(9) Uani 1 1 d . . . . .
C4A C 0.8792(2) 0.3798(3) 0.14974(18) 0.0290(6) Uani 1 1 d . . . . .
C10 C 1.0002(2) 0.3781(4) 0.1406(2) 0.0346(7) Uani 1 1 d . . . . .
C9 C 0.8760(2) 0.6859(3) 0.1172(2) 0.0296(6) Uani 1 1 d . . . . .
C5A C 1.0566(2) 0.5373(4) 0.12135(19) 0.0325(6) Uani 1 1 d . . . . .
C1 C 0.7065(2) 0.5204(3) 0.16092(19) 0.0281(6) Uani 1 1 d . . . . .
C2 C 0.6546(3) 0.3693(4) 0.1755(2) 0.0350(7) Uani 1 1 d . . . . .
H2 H 0.579760 0.366070 0.185265 0.042 Uiso 1 1 calc R U . . .
C8A C 0.9966(2) 0.6851(3) 0.11201(19) 0.0298(6) Uani 1 1 d . . . . .
C6 C 1.2223(3) 0.6880(5) 0.0932(2) 0.0504(9) Uani 1 1 d . . . . .
H6 H 1.297726 0.689187 0.086785 0.060 Uiso 1 1 calc R U . . .
C8 C 1.0508(3) 0.8339(4) 0.0931(2) 0.0372(7) Uani 1 1 d . . . . .
H8 H 1.011465 0.932256 0.086515 0.045 Uiso 1 1 calc R U . . .
C5 C 1.1691(2) 0.5396(5) 0.1120(2) 0.0413(8) Uani 1 1 d . . . . .
H5 H 1.208989 0.441646 0.118224 0.050 Uiso 1 1 calc R U . . .
C3 C 0.7148(3) 0.2233(4) 0.1753(2) 0.0382(7) Uani 1 1 d . . . . .
H3 H 0.679988 0.121667 0.183250 0.046 Uiso 1 1 calc R U . . .
C4 C 0.8257(3) 0.2287(3) 0.1635(2) 0.0352(7) Uani 1 1 d . . . . .
H4 H 0.865716 0.130547 0.164619 0.042 Uiso 1 1 calc R U . . .
C7 C 1.1633(3) 0.8347(5) 0.0841(2) 0.0450(8) Uani 1 1 d . . . . .
H7 H 1.199352 0.933885 0.071922 0.054 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 O3 1.424(3) . ?
S1 O4 1.428(3) . ?
S1 C1 1.787(3) . ?
S1 C11 1.887(4) . ?
F3 C11 1.311(4) . ?
O1 C9 1.210(4) . ?
F2 C11 1.310(4) . ?
O2 C10 1.222(4) . ?
F1 C11 1.314(5) . ?
C9A C4A 1.401(4) . ?
C9A C1 1.409(4) . ?
C9A C9 1.498(4) . ?
C4A C4 1.397(4) . ?
C4A C10 1.490(4) . ?
C10 C5A 1.482(4) . ?
C9 C8A 1.480(4) . ?
C5A C5 1.387(4) . ?
C5A C8A 1.402(4) . ?
C1 C2 1.389(4) . ?
C2 C3 1.387(5) . ?
C8A C8 1.396(4) . ?
C6 C5 1.387(5) . ?
C6 C7 1.388(6) . ?
C8 C7 1.385(5) . ?
C3 C4 1.372(5) . ?

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
O3 S1 O4 119.22(18) . . ?
O3 S1 C1 112.77(15) . . ?
O4 S1 C1 106.97(14) . . ?
O3 S1 C11 108.79(15) . . ?
O4 S1 C11 102.40(19) . . ?
C1 S1 C11 105.40(14) . . ?
C4A C9A C1 117.8(2) . . ?
C4A C9A C9 119.4(2) . . ?
C1 C9A C9 122.6(2) . . ?
F2 C11 F3 107.0(3) . . ?
F2 C11 F1 107.8(3) . . ?
F3 C11 F1 108.3(4) . . ?
F2 C11 S1 109.9(3) . . ?
F3 C11 S1 112.0(3) . . ?
F1 C11 S1 111.6(2) . . ?
C4 C4A C9A 120.3(3) . . ?
C4 C4A C10 118.3(2) . . ?
C9A C4A C10 121.4(2) . . ?
O2 C10 C5A 121.4(3) . . ?
O2 C10 C4A 120.2(3) . . ?
C5A C10 C4A 118.4(2) . . ?
O1 C9 C8A 121.4(2) . . ?
O1 C9 C9A 120.2(3) . . ?
C8A C9 C9A 118.3(2) . . ?
C5 C5A C8A 119.9(3) . . ?
C5 C5A C10 119.8(3) . . ?
C8A C5A C10 120.3(3) . . ?
C2 C1 C9A 121.2(2) . . ?
C2 C1 S1 113.1(2) . . ?
C9A C1 S1 125.58(19) . . ?
C3 C2 C1 119.8(3) . . ?
C8 C8A C5A 119.6(3) . . ?
C8 C8A C9 119.0(3) . . ?
C5A C8A C9 121.3(3) . . ?
C5 C6 C7 120.2(3) . . ?
C7 C8 C8A 119.9(3) . . ?
C5A C5 C6 120.0(3) . . ?
C4 C3 C2 120.0(3) . . ?
C3 C4 C4A 120.9(3) . . ?
C8 C7 C6 120.3(3) . . ?

_refine_diff_density_max         0.696
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.125


_exptl_crystal_colour            yellow
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1586322'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 O3 S'
_chemical_formula_weight         296.33

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'
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                   9.0948(7)
_cell_length_b                   20.0144(16)
_cell_length_c                   7.8362(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.353(9)
_cell_angle_gamma                90
_cell_volume                     1368.69(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3966
_cell_measurement_theta_min      2.4950
_cell_measurement_theta_max      27.9030

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.243
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            4917
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.1013
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.334
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4917
_reflns_number_gt                3535
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SuperFlip (Palatinus & Chapius, 2007)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component perfect twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1176P)²] 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         4917
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1666
_refine_ls_wR_factor_gt          0.1575
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.001
_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 0.66558(8) 0.63081(4) 0.21303(9) 0.0286(2) Uani 1 1 d . . . . .
O1 O 0.1946(3) 0.52541(12) -0.5023(3) 0.0429(6) Uani 1 1 d . . . . .
O3 O 1.2337(2) 0.78395(11) 0.2632(4) 0.0487(7) Uani 1 1 d . . . . .
O2 O 0.3872(2) 0.57991(11) 0.1883(3) 0.0352(6) Uani 1 1 d . . . . .
C6 C 0.6949(3) 0.61151(15) -0.1257(4) 0.0269(6) Uani 1 1 d . . . . .
H6 H 0.794123 0.627637 -0.080398 0.032 Uiso 1 1 calc R U . . .
C9 C 0.8366(3) 0.67474(15) 0.2190(4) 0.0268(6) Uani 1 1 d . . . . .
C14 C 0.9782(3) 0.64299(16) 0.2771(4) 0.0336(7) Uani 1 1 d . . . . .
H14 H 0.982472 0.597832 0.306079 0.040 Uiso 1 1 calc R U . . .
C13 C 1.1125(3) 0.67777(16) 0.2921(4) 0.0370(8) Uani 1 1 d . . . . .
H13 H 1.206307 0.655930 0.329660 0.044 Uiso 1 1 calc R U . . .
C11 C 0.9678(4) 0.77729(16) 0.1953(4) 0.0388(8) Uani 1 1 d . . . . .
H11 H 0.964220 0.822605 0.168194 0.047 Uiso 1 1 calc R U . . .
C5 C 0.6003(3) 0.60542(14) -0.0130(3) 0.0216(6) Uani 1 1 d . . . . .
C4A C 0.4507(3) 0.58077(13) -0.0836(3) 0.0215(6) Uani 1 1 d . . . . .
C8 C 0.4956(4) 0.57168(15) -0.3739(4) 0.0306(7) Uani 1 1 d . . . . .
H8 H 0.460500 0.561333 -0.494267 0.037 Uiso 1 1 calc R U . . .
C1 C 0.2389(3) 0.54141(14) -0.3458(4) 0.0298(7) Uani 1 1 d . . . . .
C12 C 1.1072(3) 0.74489(16) 0.2514(4) 0.0341(7) Uani 1 1 d . . . . .
C10 C 0.8329(3) 0.74215(16) 0.1793(4) 0.0355(7) Uani 1 1 d . . . . .
H10 H 0.739294 0.764147 0.141468 0.043 Uiso 1 1 calc R U . . .
C4 C 0.3457(3) 0.57199(14) 0.0271(4) 0.0260(6) Uani 1 1 d . . . . .
C8A C 0.3996(3) 0.56469(14) -0.2661(4) 0.0252(6) Uani 1 1 d . . . . .
C2 C 0.1362(3) 0.53906(15) -0.2318(4) 0.0355(7) Uani 1 1 d . . . . .
H2 H 0.034010 0.527603 -0.281595 0.043 Uiso 1 1 calc R U . . .
C7 C 0.6433(3) 0.59403(15) -0.3024(4) 0.0316(7) Uani 1 1 d . . . . .
H7 H 0.708828 0.597349 -0.374122 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1850(3) 0.55286(16) -0.0588(4) 0.0338(7) Uani 1 1 d . . . . .
H3 H 0.116407 0.550400 0.009368 0.041 Uiso 1 1 calc R U . . .
C15 C 1.3749(4) 0.7499(2) 0.2805(6) 0.0606(11) Uani 1 1 d . . . . .
H15A H 1.454835 0.782018 0.287506 0.091 Uiso 1 1 calc R U . . .
H15B H 1.399643 0.723260 0.386611 0.091 Uiso 1 1 calc R U . . .
H15C H 1.365266 0.721611 0.179064 0.091 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 C9 1.776(3) . ?
S1 C5 1.777(3) . ?
O1 C1 1.221(4) . ?
O3 C12 1.373(4) . ?
O3 C15 1.426(4) . ?
O2 C4 1.222(3) . ?
C6 C7 1.376(4) . ?
C6 C5 1.400(4) . ?
C9 C10 1.383(4) . ?
C9 C14 1.393(4) . ?
C14 C13 1.381(4) . ?
C13 C12 1.378(5) . ?
C11 C12 1.381(4) . ?
C11 C10 1.388(4) . ?
C5 C4A 1.406(4) . ?
C4A C8A 1.411(4) . ?
C4A C4 1.470(4) . ?
C8 C7 1.377(4) . ?
C8 C8A 1.382(4) . ?
C1 C2 1.464(5) . ?
C1 C8A 1.493(4) . ?
C4 C3 1.478(4) . ?
C2 C3 1.331(5) . ?

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
C9 S1 C5 102.25(13) . . ?
C12 O3 C15 116.7(3) . . ?
C7 C6 C5 121.1(3) . . ?
C10 C9 C14 118.7(3) . . ?
C10 C9 S1 120.8(2) . . ?
C14 C9 S1 120.4(2) . . ?
C13 C14 C9 120.8(3) . . ?
C12 C13 C14 119.9(3) . . ?
C12 C11 C10 119.9(3) . . ?
C6 C5 C4A 118.7(2) . . ?
C6 C5 S1 120.8(2) . . ?
C4A C5 S1 120.5(2) . . ?
C5 C4A C8A 119.0(2) . . ?
C5 C4A C4 121.8(2) . . ?
C8A C4A C4 119.2(2) . . ?
C7 C8 C8A 119.7(3) . . ?
O1 C1 C2 121.2(3) . . ?
O1 C1 C8A 120.6(3) . . ?
C2 C1 C8A 118.2(3) . . ?
O3 C12 C13 124.4(3) . . ?
O3 C12 C11 115.5(3) . . ?
C13 C12 C11 120.0(3) . . ?
C9 C10 C11 120.6(3) . . ?
O2 C4 C4A 122.1(2) . . ?
O2 C4 C3 118.9(3) . . ?
C4A C4 C3 119.1(2) . . ?
C8 C8A C4A 120.8(3) . . ?
C8 C8A C1 119.2(2) . . ?
C4A C8A C1 120.0(2) . . ?
C3 C2 C1 121.9(3) . . ?
C6 C7 C8 120.6(3) . . ?
C2 C3 C4 121.4(3) . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1586747'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H5 F3 O3 S'
_chemical_formula_weight         274.21

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.0423(4)
_cell_length_b                   8.0926(5)
_cell_length_c                   9.4378(6)
_cell_angle_alpha                68.147(6)
_cell_angle_beta                 84.221(5)
_cell_angle_gamma                72.377(5)
_cell_volume                     543.30(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3092
_cell_measurement_theta_min      2.2970
_cell_measurement_theta_max      27.0440

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    0.336
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            8889
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.325
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2210
_reflns_number_gt                1820
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SuperFlip (Palatinus & Chapius, 2007)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0475P)²+0.1880P] 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         2210
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2202(3) 0.4625(3) 0.0994(3) 0.0599(6) Uani 1 1 d . . . . .
C2 C 1.2738(3) 0.6320(4) 0.0618(3) 0.0694(7) Uani 1 1 d . . . . .
H201 H 1.373351 0.644656 0.000117 0.083 Uiso 1 1 calc R U . . .
C3 C 1.1885(3) 0.7674(3) 0.1108(3) 0.0613(6) Uani 1 1 d . . . . .
H200 H 1.228433 0.874271 0.082977 0.074 Uiso 1 1 calc R U . . .
C4 C 1.0344(3) 0.7578(3) 0.2065(2) 0.0475(5) Uani 1 1 d . . . . .
C4A C 0.9777(2) 0.5872(2) 0.2530(2) 0.0402(4) Uani 1 1 d . . . . .
C5 C 0.8373(2) 0.5660(3) 0.3505(2) 0.0428(4) Uani 1 1 d . . . . .
C6 C 0.7841(3) 0.4064(3) 0.3927(3) 0.0571(6) Uani 1 1 d . . . . .
H100 H 0.688582 0.391948 0.459402 0.069 Uiso 1 1 calc R U . . .
C7 C 0.8721(3) 0.2684(3) 0.3361(3) 0.0665(7) Uani 1 1 d . . . . .
H11 H 0.834564 0.160193 0.362620 0.080 Uiso 1 1 calc R U . . .
C8 C 1.0124(3) 0.2859(3) 0.2427(3) 0.0599(6) Uani 1 1 d . . . . .
H101 H 1.073424 0.188503 0.207355 0.072 Uiso 1 1 calc R U . . .
C8A C 1.0656(3) 0.4453(3) 0.1996(2) 0.0473(5) Uani 1 1 d . . . . .
C9 C 0.5735(3) 0.8968(3) 0.2910(3) 0.0595(6) Uani 1 1 d . . . . .
O1 O 1.2978(2) 0.3419(3) 0.0500(2) 0.0851(6) Uani 1 1 d . . . . .
O2 O 0.9523(2) 0.8869(2) 0.2450(2) 0.0686(5) Uani 1 1 d . . . . .
O3 O 0.6231(2) 0.6318(2) 0.56540(18) 0.0646(4) Uani 1 1 d . . . . .
S1 S 0.73313(7) 0.72507(7) 0.44783(6) 0.04803(18) Uani 1 1 d . . . . .
F1 F 0.4619(19) 0.798(2) 0.2836(16) 0.115(5) Uani 0.39(2) 1 d . . P A 1
F3 F 0.482(3) 1.026(3) 0.3329(15) 0.153(9) Uani 0.39(2) 1 d . . P A 1
F5 F 0.624(2) 0.943(3) 0.1596(15) 0.098(5) Uani 0.39(2) 1 d . . P A 1
F2 F 0.4195(5) 0.8846(12) 0.3251(7) 0.090(2) Uani 0.61(2) 1 d . . P A 2
F4 F 0.5739(10) 1.0676(6) 0.2833(9) 0.091(2) Uani 0.61(2) 1 d . . P A 2
F6 F 0.6124(15) 0.8996(15) 0.1544(10) 0.091(3) Uani 0.61(2) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.212(3) . ?
C1 C2 1.470(4) . ?
C1 C8A 1.493(3) . ?
C2 C3 1.320(3) . ?
C3 C4 1.463(3) . ?
C4 O2 1.215(3) . ?
C4 C4A 1.481(3) . ?
C4A C8A 1.393(3) . ?
C4A C5 1.394(3) . ?
C5 C6 1.388(3) . ?
C5 S1 1.810(2) . ?
C6 C7 1.386(3) . ?
C7 C8 1.369(3) . ?
C8 C8A 1.386(3) . ?
C9 F5 1.220(12) . ?
C9 F3 1.255(7) . ?
C9 F2 1.272(5) . ?
C9 F6 1.289(9) . ?
C9 F4 1.357(5) . ?
C9 F1 1.392(10) . ?
C9 S1 1.882(2) . ?
O3 S1 1.4723(16) . ?

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 C1 C2 121.3(2) . . ?
O1 C1 C8A 121.4(2) . . ?
C2 C1 C8A 117.4(2) . . ?
C3 C2 C1 122.4(2) . . ?
C2 C3 C4 122.0(2) . . ?
O2 C4 C3 121.33(19) . . ?
O2 C4 C4A 120.47(19) . . ?
C3 C4 C4A 118.19(19) . . ?
C8A C4A C5 119.18(17) . . ?
C8A C4A C4 119.99(18) . . ?
C5 C4A C4 120.82(17) . . ?
C6 C5 C4A 120.54(19) . . ?
C6 C5 S1 115.99(16) . . ?
C4A C5 S1 123.00(14) . . ?
C7 C6 C5 119.1(2) . . ?
C8 C7 C6 120.9(2) . . ?
C7 C8 C8A 120.2(2) . . ?
C8 C8A C4A 120.0(2) . . ?
C8 C8A C1 120.0(2) . . ?
C4A C8A C1 120.02(19) . . ?
F5 C9 F3 116.1(10) . . ?
F2 C9 F6 111.5(6) . . ?
F2 C9 F4 107.0(3) . . ?
F6 C9 F4 103.6(5) . . ?
F5 C9 F1 100.3(8) . . ?
F3 C9 F1 106.2(7) . . ?
F5 C9 S1 119.0(8) . . ?
F3 C9 S1 109.4(4) . . ?
F2 C9 S1 111.0(3) . . ?
F6 C9 S1 117.0(5) . . ?
F4 C9 S1 105.9(3) . . ?
F1 C9 S1 103.8(4) . . ?
O3 S1 C5 105.97(9) . . ?
O3 S1 C9 103.70(11) . . ?
C5 S1 C9 97.15(10) . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1586324'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 Br O2 S'
_chemical_formula_sum            'C16 H9 Br O2 S'
_chemical_formula_weight         345.20

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.8595(5)
_cell_length_b                   7.9836(5)
_cell_length_c                   12.2941(7)
_cell_angle_alpha                89.939(5)
_cell_angle_beta                 74.827(5)
_cell_angle_gamma                68.477(6)
_cell_volume                     688.73(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    4147
_cell_measurement_theta_min      3.3370
_cell_measurement_theta_max      25.9000

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Dark Orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.113
_exptl_absorpt_coefficient_mu    3.132
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_T_max  0.796
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            18417
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.758
_diffrn_reflns_theta_max         29.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3541
_reflns_number_gt                2223
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SuperFlip (Palatinus & Chapius, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0245P)²+0.2982P] 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         3541
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.26937(5) 0.26559(5) 0.09408(3) 0.07821(16) Uani 1 1 d . . . . .
S1 S 1.06230(9) 0.24278(9) -0.23629(6) 0.04502(18) Uani 1 1 d . . . . .
O2 O 1.4177(3) 0.2141(2) -0.34983(16) 0.0492(5) Uani 1 1 d . . . . .
O1 O 1.7667(3) -0.5010(3) -0.44031(18) 0.0602(5) Uani 1 1 d . . . . .
C12 C 0.5023(4) 0.2614(3) -0.0039(2) 0.0449(7) Uani 1 1 d . . . . .
C13 C 0.6580(4) 0.2198(4) 0.0366(2) 0.0532(7) Uani 1 1 d . . . . .
H13 H 0.6490 0.1956 0.1123 0.064 Uiso 1 1 calc R U . . .
C7 C 1.1801(4) -0.2932(4) -0.2987(2) 0.0450(7) Uani 1 1 d . . . . .
H7 H 1.1106 -0.3688 -0.2876 0.054 Uiso 1 1 calc R U . . .
C4A C 1.3816(3) -0.0659(3) -0.33551(18) 0.0301(5) Uani 1 1 d . . . . .
C3 C 1.7011(4) -0.0390(4) -0.4129(2) 0.0444(6) Uani 1 1 d . . . . .
H3 H 1.7739 0.0336 -0.4260 0.053 Uiso 1 1 calc R U . . .
C5 C 1.1843(3) 0.0073(3) -0.28174(19) 0.0320(5) Uani 1 1 d . . . . .
C8A C 1.4743(3) -0.2543(3) -0.36609(19) 0.0331(5) Uani 1 1 d . . . . .
C4 C 1.4935(3) 0.0491(3) -0.36357(19) 0.0351(6) Uani 1 1 d . . . . .
C8 C 1.3737(4) -0.3664(3) -0.3484(2) 0.0411(6) Uani 1 1 d . . . . .
H8 H 1.4368 -0.4915 -0.3701 0.049 Uiso 1 1 calc R U . . .
C1 C 1.6842(4) -0.3376(4) -0.4177(2) 0.0408(6) Uani 1 1 d . . . . .
C14 C 0.8276(4) 0.2137(4) -0.0347(2) 0.0487(7) Uani 1 1 d . . . . .
H14 H 0.9347 0.1862 -0.0073 0.058 Uiso 1 1 calc R U . . .
C2 C 1.7893(4) -0.2158(4) -0.4396(2) 0.0459(7) Uani 1 1 d . . . . .
H2 H 1.9217 -0.2649 -0.4732 0.055 Uiso 1 1 calc R U . . .
C6 C 1.0866(3) -0.1100(3) -0.2650(2) 0.0395(6) Uani 1 1 d . . . . .
H6 H 0.9546 -0.0631 -0.2300 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6822(4) 0.2932(4) -0.1850(2) 0.0444(6) Uani 1 1 d . . . . .
H10 H 0.6900 0.3196 -0.2602 0.053 Uiso 1 1 calc R U . . .
C9 C 0.8420(3) 0.2476(3) -0.1463(2) 0.0382(6) Uani 1 1 d . . . . .
C11 C 0.5107(4) 0.2999(4) -0.1135(2) 0.0484(7) Uani 1 1 d . . . . .
H11 H 0.4020 0.3304 -0.1396 0.058 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
Br1 C12 1.898(3) . ?
S1 C5 1.779(2) . ?
S1 C9 1.781(3) . ?
O2 C4 1.221(3) . ?
O1 C1 1.219(3) . ?
C12 C11 1.371(4) . ?
C12 C13 1.370(4) . ?
C13 C14 1.374(4) . ?
C13 H13 0.9400 . ?
C7 C8 1.375(4) . ?
C7 C6 1.380(3) . ?
C7 H7 0.9400 . ?
C4A C5 1.408(3) . ?
C4A C8A 1.410(3) . ?
C4A C4 1.473(3) . ?
C3 C2 1.321(4) . ?
C3 C4 1.472(3) . ?
C3 H3 0.9400 . ?
C5 C6 1.397(3) . ?
C8A C8 1.379(3) . ?
C8A C1 1.488(3) . ?
C8 H8 0.9400 . ?
C1 C2 1.474(4) . ?
C14 C9 1.381(4) . ?
C14 H14 0.9400 . ?
C2 H2 0.9400 . ?
C6 H6 0.9400 . ?
C10 C9 1.384(4) . ?
C10 C11 1.385(4) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?

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
C5 S1 C9 101.19(11) . . ?
C11 C12 C13 121.6(3) . . ?
C11 C12 Br1 119.3(2) . . ?
C13 C12 Br1 119.2(2) . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C5 C4A C8A 119.2(2) . . ?
C5 C4A C4 121.9(2) . . ?
C8A C4A C4 118.9(2) . . ?
C2 C3 C4 122.7(2) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C6 C5 C4A 118.3(2) . . ?
C6 C5 S1 120.79(18) . . ?
C4A C5 S1 120.96(17) . . ?
C8 C8A C4A 121.1(2) . . ?
C8 C8A C1 118.2(2) . . ?
C4A C8A C1 120.7(2) . . ?
O2 C4 C3 119.8(2) . . ?
O2 C4 C4A 121.7(2) . . ?
C3 C4 C4A 118.5(2) . . ?
C7 C8 C8A 119.4(2) . . ?
C7 C8 H8 120.3 . . ?
C8A C8 H8 120.3 . . ?
O1 C1 C2 121.1(2) . . ?
O1 C1 C8A 121.2(2) . . ?
C2 C1 C8A 117.7(2) . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C14 C9 C10 119.3(2) . . ?
C14 C9 S1 119.7(2) . . ?
C10 C9 S1 120.9(2) . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1586323'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H4 F6 O2 S2'
_chemical_formula_sum            'C12 H4 F6 O2 S2'
_chemical_formula_weight         358.27

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'
F F 0.0727 0.0534 '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'

_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                   4.67670(10)
_cell_length_b                   19.3071(3)
_cell_length_c                   14.5648(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.9490(10)
_cell_angle_gamma                90
_cell_volume                     1302.47(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6243
_cell_measurement_theta_min      3.8090
_cell_measurement_theta_max      66.4230

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    4.489
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.366
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            11706
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.825
_diffrn_reflns_theta_max         66.544
_diffrn_reflns_theta_full        66.544
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2307
_reflns_number_gt                1984
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SuperFlip (Palatinus & Chapius, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0518P)²+0.2550P] 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         2307
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_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
S2 S 0.65654(12) 0.47099(3) 0.24868(3) 0.03108(17) Uani 1 1 d . . . . .
S1 S -0.01470(12) 0.21013(3) 0.05288(4) 0.03067(17) Uani 1 1 d . . . . .
F6 F 0.3701(3) 0.46015(7) 0.39394(10) 0.0426(3) Uani 1 1 d . . . . .
F3 F -0.3204(3) 0.19605(7) 0.19332(10) 0.0409(3) Uani 1 1 d . . . . .
F4 F 0.7489(3) 0.39767(8) 0.40175(10) 0.0490(4) Uani 1 1 d . . . . .
F2 F 0.0837(3) 0.14282(7) 0.21321(10) 0.0436(3) Uani 1 1 d . . . . .
F1 F -0.2592(3) 0.10652(7) 0.11132(11) 0.0502(4) Uani 1 1 d . . . . .
F5 F 0.7863(3) 0.50840(8) 0.41416(9) 0.0469(4) Uani 1 1 d . . . . .
O1 O 0.2034(4) 0.26605(9) -0.08126(10) 0.0392(4) Uani 1 1 d . . . . .
O2 O 0.7727(4) 0.47951(9) 0.08210(11) 0.0437(4) Uani 1 1 d . . . . .
C8 C 0.1658(4) 0.28235(10) 0.10962(14) 0.0241(4) Uani 1 1 d . . . . .
C4A C 0.4834(4) 0.38249(10) 0.10332(13) 0.0231(4) Uani 1 1 d . . . . .
C8A C 0.3332(4) 0.32522(10) 0.05991(13) 0.0223(4) Uani 1 1 d . . . . .
C5 C 0.4682(4) 0.39794(10) 0.19673(13) 0.0242(4) Uani 1 1 d . . . . .
C9 C -0.1298(5) 0.16275(11) 0.14849(16) 0.0325(5) Uani 1 1 d . . . . .
C10 C 0.6337(5) 0.45727(11) 0.37008(15) 0.0317(5) Uani 1 1 d . . . . .
C7 C 0.1545(5) 0.29864(11) 0.20235(14) 0.0287(5) Uani 1 1 d . . . . .
H8 H 0.0455 0.2709 0.2366 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2999(5) 0.35447(11) 0.24455(14) 0.0291(5) Uani 1 1 d . . . . .
H7 H 0.2862 0.3636 0.3065 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6624(5) 0.42579(11) 0.04941(15) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.5622(5) 0.34995(12) -0.08488(15) 0.0345(5) Uani 1 1 d . . . . .
H2 H 0.5949 0.3371 -0.1441 0.041 Uiso 1 1 calc R U . . .
C1 C 0.3555(5) 0.31009(11) -0.03880(14) 0.0272(4) Uani 1 1 d . . . . .
C3 C 0.7030(5) 0.40362(12) -0.04432(15) 0.0344(5) Uani 1 1 d . . . . .
H3 H 0.8308 0.4279 -0.0759 0.041 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
S2 C5 1.776(2) . ?
S2 C10 1.806(2) . ?
S1 C8 1.774(2) . ?
S1 C9 1.809(2) . ?
F6 C10 1.327(3) . ?
F3 C9 1.340(3) . ?
F4 C10 1.326(3) . ?
F2 C9 1.331(3) . ?
F1 C9 1.322(3) . ?
F5 C10 1.330(3) . ?
O1 C1 1.221(3) . ?
O2 C4 1.225(3) . ?
C8 C7 1.395(3) . ?
C8 C8A 1.407(3) . ?
C4A C5 1.404(3) . ?
C4A C8A 1.412(3) . ?
C4A C4 1.483(3) . ?
C8A C1 1.485(3) . ?
C5 C6 1.400(3) . ?
C7 C6 1.373(3) . ?
C7 H8 0.9300 . ?
C6 H7 0.9300 . ?
C4 C3 1.468(3) . ?
C2 C3 1.322(3) . ?
C2 C1 1.468(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?

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
C5 S2 C10 101.99(10) . . ?
C8 S1 C9 102.24(10) . . ?
C7 C8 C8A 117.64(18) . . ?
C7 C8 S1 123.30(16) . . ?
C8A C8 S1 119.05(15) . . ?
C5 C4A C8A 120.78(17) . . ?
C5 C4A C4 120.08(18) . . ?
C8A C4A C4 119.13(17) . . ?
C8 C8A C4A 120.53(17) . . ?
C8 C8A C1 120.09(18) . . ?
C4A C8A C1 119.37(17) . . ?
C6 C5 C4A 117.51(18) . . ?
C6 C5 S2 122.95(15) . . ?
C4A C5 S2 119.54(15) . . ?
F1 C9 F2 107.99(17) . . ?
F1 C9 F3 107.19(18) . . ?
F2 C9 F3 106.15(18) . . ?
F1 C9 S1 105.55(15) . . ?
F2 C9 S1 114.66(16) . . ?
F3 C9 S1 114.91(15) . . ?
F4 C10 F6 107.01(19) . . ?
F4 C10 F5 108.14(18) . . ?
F6 C10 F5 107.35(17) . . ?
F4 C10 S2 113.06(15) . . ?
F6 C10 S2 115.65(16) . . ?
F5 C10 S2 105.27(15) . . ?
C6 C7 C8 121.85(19) . . ?
C6 C7 H8 119.1 . . ?
C8 C7 H8 119.1 . . ?
C7 C6 C5 121.68(19) . . ?
C7 C6 H7 119.2 . . ?
C5 C6 H7 119.2 . . ?
O2 C4 C3 120.44(19) . . ?
O2 C4 C4A 120.66(19) . . ?
C3 C4 C4A 118.90(18) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
O1 C1 C2 120.52(19) . . ?
O1 C1 C8A 120.89(19) . . ?
C2 C1 C8A 118.58(18) . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1586325'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H7 F3 O2 S'
_chemical_formula_sum            'C15 H7 F3 O2 S'
_chemical_formula_weight         308.27

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.4794(7)
_cell_length_b                   7.9785(8)
_cell_length_c                   11.9788(10)
_cell_angle_alpha                95.823(8)
_cell_angle_beta                 102.310(8)
_cell_angle_gamma                113.691(9)
_cell_volume                     625.39(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    2451
_cell_measurement_theta_min      3.5610
_cell_measurement_theta_max      28.6430

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.859
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.297
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            10141
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.851
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2559
_reflns_number_gt                1955
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SuperFlip (Palatinus & Chapius, 2007)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0438P)²+0.0796P] 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         2559
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.95483(8) 0.66386(7) 0.20699(4) 0.04899(18) Uani 1 1 d . . . . .
F3 F 0.6927(2) 0.7069(2) 0.03686(12) 0.0875(5) Uani 1 1 d . . . . .
F2 F 0.9825(2) 0.7721(2) 0.00731(10) 0.0771(4) Uani 1 1 d . . . . .
F1 F 0.7807(2) 0.4868(2) 0.00070(11) 0.0844(5) Uani 1 1 d . . . . .
O1 O 1.1219(2) 0.65658(18) 0.41274(11) 0.0548(4) Uani 1 1 d . . . . .
O2 O 1.4050(2) 1.36948(18) 0.62951(12) 0.0571(4) Uani 1 1 d . . . . .
C8A C 1.3023(2) 0.8827(2) 0.58714(15) 0.0331(4) Uani 1 1 d . . . . .
C4A C 1.2294(3) 1.1440(2) 0.45384(15) 0.0324(4) Uani 1 1 d . . . . .
C9A C 1.1540(2) 0.9566(2) 0.39654(14) 0.0309(4) Uani 1 1 d . . . . .
C5A C 1.3790(3) 1.0693(2) 0.64370(15) 0.0351(4) Uani 1 1 d . . . . .
C4 C 1.1991(3) 1.2736(2) 0.39393(16) 0.0406(4) Uani 1 1 d . . . . .
H4 H 1.249772 1.398800 0.432664 0.049 Uiso 1 1 calc R U . . .
C1 C 1.0476(3) 0.9018(2) 0.27712(15) 0.0361(4) Uani 1 1 d . . . . .
C8 C 1.3335(3) 0.7539(3) 0.64881(16) 0.0421(5) Uani 1 1 d . . . . .
H8 H 1.281797 0.628059 0.611049 0.050 Uiso 1 1 calc R U . . .
C10 C 1.3434(3) 1.2077(2) 0.58030(16) 0.0370(4) Uani 1 1 d . . . . .
C9 C 1.1880(3) 0.8195(2) 0.46176(15) 0.0344(4) Uani 1 1 d . . . . .
C3 C 1.0944(3) 1.2187(3) 0.27732(17) 0.0475(5) Uani 1 1 d . . . . .
H3 H 1.073852 1.307157 0.236707 0.057 Uiso 1 1 calc R U . . .
C7 C 1.4403(3) 0.8108(3) 0.76543(17) 0.0512(5) Uani 1 1 d . . . . .
H7 H 1.461778 0.723751 0.807112 0.061 Uiso 1 1 calc R U . . .
C2 C 1.0195(3) 1.0365(3) 0.21938(16) 0.0451(5) Uani 1 1 d . . . . .
H2 H 0.948166 1.001954 0.139655 0.054 Uiso 1 1 calc R U . . .
C5 C 1.4855(3) 1.1245(3) 0.76126(17) 0.0468(5) Uani 1 1 d . . . . .
H5 H 1.536787 1.249753 0.799999 0.056 Uiso 1 1 calc R U . . .
C11 C 0.8498(4) 0.6631(3) 0.05789(19) 0.0601(6) Uani 1 1 d . . . . .
C6 C 1.5158(3) 0.9952(3) 0.82105(18) 0.0552(6) Uani 1 1 d . . . . .
H6 H 1.588718 1.033060 0.900563 0.066 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 C1 1.7776(18) . ?
S1 C11 1.790(2) . ?
F3 C11 1.337(3) . ?
F2 C11 1.334(3) . ?
F1 C11 1.336(2) . ?
O1 C9 1.218(2) . ?
O2 C10 1.216(2) . ?
C8A C8 1.389(2) . ?
C8A C5A 1.395(2) . ?
C8A C9 1.481(2) . ?
C4A C4 1.380(2) . ?
C4A C9A 1.406(2) . ?
C4A C10 1.492(2) . ?
C9A C1 1.407(2) . ?
C9A C9 1.478(2) . ?
C5A C5 1.388(2) . ?
C5A C10 1.479(2) . ?
C4 C3 1.375(3) . ?
C4 H4 0.9400 . ?
C1 C2 1.396(2) . ?
C8 C7 1.378(3) . ?
C8 H8 0.9400 . ?
C3 C2 1.372(3) . ?
C3 H3 0.9400 . ?
C7 C6 1.378(3) . ?
C7 H7 0.9400 . ?
C2 H2 0.9400 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?

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
C1 S1 C11 102.83(10) . . ?
C8 C8A C5A 119.79(16) . . ?
C8 C8A C9 119.26(15) . . ?
C5A C8A C9 120.95(15) . . ?
C4 C4A C9A 120.50(16) . . ?
C4 C4A C10 118.49(15) . . ?
C9A C4A C10 121.01(15) . . ?
C4A C9A C1 119.41(15) . . ?
C4A C9A C9 119.89(15) . . ?
C1 C9A C9 120.70(15) . . ?
C5 C5A C8A 119.66(16) . . ?
C5 C5A C10 119.70(16) . . ?
C8A C5A C10 120.62(15) . . ?
C3 C4 C4A 119.69(17) . . ?
C3 C4 H4 120.2 . . ?
C4A C4 H4 120.2 . . ?
C2 C1 C9A 118.52(16) . . ?
C2 C1 S1 123.12(14) . . ?
C9A C1 S1 118.36(13) . . ?
C7 C8 C8A 119.93(18) . . ?
C7 C8 H8 120.0 . . ?
C8A C8 H8 120.0 . . ?
O2 C10 C5A 121.16(16) . . ?
O2 C10 C4A 120.49(16) . . ?
C5A C10 C4A 118.35(15) . . ?
O1 C9 C9A 120.17(15) . . ?
O1 C9 C8A 120.68(15) . . ?
C9A C9 C8A 119.15(14) . . ?
C2 C3 C4 120.93(17) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C6 C7 C8 120.14(18) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C3 C2 C1 120.95(17) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C6 C5 C5A 119.84(18) . . ?
C6 C5 H5 120.1 . . ?
C5A C5 H5 120.1 . . ?
F2 C11 F1 107.22(18) . . ?
F2 C11 F3 106.1(2) . . ?
F1 C11 F3 106.74(18) . . ?
F2 C11 S1 114.96(16) . . ?
F1 C11 S1 105.18(16) . . ?
F3 C11 S1 116.09(16) . . ?
C5 C6 C7 120.64(18) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 1586328'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_vrf_PLAT097_shelx               
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       3.19 eA-3 
RESPONSE: Possible disordered S-CF3 group, but all atempts to model it has 
failed.
;

_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Residual Density  0.81A From      S1       3.36 eA-3
RESPONSE: Possible disordered S-CF3 group, but all atempts to model it has 
failed.
;

_vrf_DIFMN02_shelx               
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*0.75
            _refine_diff_density_min given =     -1.219
            Test value =     -1.200
RESPONSE: Possible disordered S-CF3 group, but all atempts to model it has 
failed.
;

_vrf_DIFMN03_shelx               
;
PROBLEM:  The minimum difference density is < -0.1*ZMAX*0.75
            The relevant atom site should be identified.
RESPONSE: Possible disordered S-CF3 group, but all atempts to model it has 
failed.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F3 O3 S'
_chemical_formula_sum            'C13 H9 F3 O3 S'
_chemical_formula_weight         302.26

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.5769(4)
_cell_length_b                   11.1576(2)
_cell_length_c                   31.0437(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.048(2)
_cell_angle_gamma                90
_cell_volume                     4937.8(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    10365
_cell_measurement_theta_min      2.8910
_cell_measurement_theta_max      66.4390

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             2464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.277
_exptl_crystal_size_min          0.113
_exptl_absorpt_coefficient_mu    2.771
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.474
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            33710
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.911
_diffrn_reflns_theta_max         66.550
_diffrn_reflns_theta_full        66.550
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4330
_reflns_number_gt                3705
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0856P)²+42.1184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00017(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4330
_refine_ls_number_parameters     362
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0830
_refine_ls_wR_factor_ref         0.2103
_refine_ls_wR_factor_gt          0.2014
_refine_ls_goodness_of_fit_ref   1.026
_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
S2 S 0.73635(8) -0.15580(10) 0.11819(4) 0.0379(3) Uani 1 1 d . . . . .
S1 S 0.93691(10) 0.37127(12) 0.09753(5) 0.0502(4) Uani 1 1 d . U . . .
F5 F 0.8364(2) -0.3528(3) 0.14449(11) 0.0593(9) Uani 1 1 d . . . . .
O6 O 0.9050(2) 0.1193(3) 0.27960(10) 0.0394(8) Uani 1 1 d . . . . .
F6 F 0.7146(2) -0.3348(3) 0.17157(12) 0.0617(9) Uani 1 1 d . . . . .
O4 O 0.7043(3) 0.0570(3) 0.09287(10) 0.0435(8) Uani 1 1 d . . . . .
O1 O 0.9885(3) -0.1972(3) 0.11649(11) 0.0487(9) Uani 1 1 d . . . . .
F4 F 0.7004(3) -0.3729(3) 0.10268(12) 0.0718(11) Uani 1 1 d . . . . .
O2 O 0.9984(3) 0.2544(3) 0.16912(11) 0.0490(9) Uani 1 1 d . . . . .
O5 O 0.8428(3) 0.3127(3) 0.23637(12) 0.0586(11) Uani 1 1 d . . . . .
O3 O 0.9151(3) -0.1360(3) 0.03596(11) 0.0503(9) Uani 1 1 d . . . . .
C1 C 0.9960(3) -0.0907(4) 0.12547(14) 0.0340(10) Uani 1 1 d . . . . .
C16 C 0.8702(3) 0.0546(4) 0.24311(14) 0.0322(9) Uani 1 1 d . . . . .
C19A C 0.7832(3) 0.0498(4) 0.16706(13) 0.0287(9) Uani 1 1 d . . . . .
C21 C 0.7495(4) -0.3097(4) 0.13591(17) 0.0452(12) Uani 1 1 d . . . . .
C18 C 0.8435(3) -0.1327(4) 0.20351(15) 0.0362(10) Uani 1 1 d . . . . .
H18 H 0.8522 -0.2152 0.2029 0.043 Uiso 1 1 calc R U . . .
C14 C 0.7601(4) 0.3050(4) 0.16398(16) 0.0406(11) Uani 1 1 d . . . . .
H14 H 0.7527 0.3879 0.1638 0.049 Uiso 1 1 calc R U . . .
C12 C 0.7347(3) 0.1139(4) 0.12686(14) 0.0321(9) Uani 1 1 d . . . . .
C15A C 0.8219(3) 0.1157(4) 0.20560(14) 0.0309(9) Uani 1 1 d . . . . .
C13 C 0.7237(3) 0.2457(4) 0.12723(14) 0.0346(10) Uani 1 1 d . . . . .
C2 C 1.0466(3) -0.0549(4) 0.16955(14) 0.0355(10) Uani 1 1 d . . . . .
H2 H 1.0755 -0.1143 0.1887 0.043 Uiso 1 1 calc R U . . .
C19 C 0.7917(3) -0.0753(4) 0.16610(14) 0.0311(9) Uani 1 1 d . . . . .
C15 C 0.8111(3) 0.2488(4) 0.20498(15) 0.0370(10) Uani 1 1 d . . . . .
C8A C 0.9564(3) 0.0049(4) 0.09316(14) 0.0336(10) Uani 1 1 d . . . . .
C22 C 0.9538(4) 0.0554(5) 0.31791(15) 0.0429(12) Uani 1 1 d . . . . .
H22A H 0.9750 0.1111 0.3415 0.064 Uiso 1 1 calc R U . . .
H22B H 0.9121 -0.0017 0.3268 0.064 Uiso 1 1 calc R U . . .
H22C H 1.0067 0.0142 0.3110 0.064 Uiso 1 1 calc R U . . .
C4A C 0.9617(3) 0.1248(4) 0.10763(14) 0.0323(9) Uani 1 1 d . . . . .
C3 C 1.0534(3) 0.0585(4) 0.18376(14) 0.0336(10) Uani 1 1 d . . . . .
C5 C 0.9266(3) 0.2185(4) 0.07878(14) 0.0360(10) Uani 1 1 d . . . . .
C4 C 1.0046(3) 0.1533(4) 0.15447(14) 0.0333(10) Uani 1 1 d . . . . .
C17 C 0.8817(3) -0.0701(4) 0.24121(14) 0.0360(10) Uani 1 1 d . . . . .
H17 H 0.9154 -0.1107 0.2656 0.043 Uiso 1 1 calc R U . . .
C8 C 0.9165(3) -0.0217(5) 0.04896(15) 0.0388(11) Uani 1 1 d . . . . .
C11 C 0.8777(4) -0.1628(5) -0.00964(17) 0.0515(13) Uani 1 1 d . . . . .
H11A H 0.8810 -0.2476 -0.0143 0.077 Uiso 1 1 calc R U . . .
H11B H 0.8136 -0.1371 -0.0174 0.077 Uiso 1 1 calc R U . . .
H11C H 0.9137 -0.1216 -0.0277 0.077 Uiso 1 1 calc R U . . .
C7 C 0.8793(4) 0.0726(5) 0.02088(15) 0.0428(11) Uani 1 1 d . . . . .
H7 H 0.8510 0.0562 -0.0082 0.051 Uiso 1 1 calc R U . . .
C6 C 0.8838(4) 0.1891(5) 0.03566(16) 0.0437(12) Uani 1 1 d . . . . .
H6 H 0.8577 0.2497 0.0164 0.052 Uiso 1 1 calc R U . . .
C9 C 1.1037(4) 0.0967(5) 0.22868(15) 0.0416(11) Uani 1 1 d . . . . .
H9A H 1.0993 0.1821 0.2313 0.062 Uiso 0.5 1 calc R U P . .
H9B H 1.0757 0.0586 0.2505 0.062 Uiso 0.5 1 calc R U P . .
H9C H 1.1685 0.0739 0.2331 0.062 Uiso 0.5 1 calc R U P . .
H9D H 1.1298 0.0276 0.2453 0.062 Uiso 0.5 1 calc R U P . .
H9E H 1.1533 0.1512 0.2261 0.062 Uiso 0.5 1 calc R U P . .
H9F H 1.0605 0.1358 0.2435 0.062 Uiso 0.5 1 calc R U P . .
C20 C 0.6743(4) 0.3036(4) 0.08529(16) 0.0440(12) Uani 1 1 d . . . . .
H20A H 0.6542 0.2431 0.0634 0.066 Uiso 0.5 1 calc R U P . .
H20B H 0.6207 0.3469 0.0904 0.066 Uiso 0.5 1 calc R U P . .
H20C H 0.7163 0.3580 0.0752 0.066 Uiso 0.5 1 calc R U P . .
H20D H 0.6732 0.3889 0.0893 0.066 Uiso 0.5 1 calc R U P . .
H20E H 0.7068 0.2851 0.0622 0.066 Uiso 0.5 1 calc R U P . .
H20F H 0.6112 0.2740 0.0775 0.066 Uiso 0.5 1 calc R U P . .
F2 F 0.8393(5) 0.4543(4) 0.02336(16) 0.129(2) Uani 1 1 d . . . . .
F3 F 0.9793(6) 0.4106(4) 0.02181(19) 0.136(3) Uani 1 1 d . . . . .
F1 F 0.9494(4) 0.5637(3) 0.05994(15) 0.1001(16) Uani 1 1 d . . . . .
C10 C 0.9253(7) 0.4496(6) 0.0485(3) 0.079(2) 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
S2 C19 1.780(4) . ?
S2 C21 1.801(5) . ?
S1 C10 1.732(7) . ?
S1 C5 1.797(5) . ?
F5 C21 1.329(6) . ?
O6 C16 1.350(5) . ?
O6 C22 1.440(5) . ?
F6 C21 1.341(7) . ?
O4 C12 1.232(5) . ?
O1 C1 1.220(6) . ?
F4 C21 1.329(6) . ?
O2 C4 1.227(6) . ?
O5 C15 1.218(6) . ?
O3 C8 1.336(6) . ?
O3 C11 1.438(6) . ?
C1 C2 1.468(6) . ?
C1 C8A 1.495(6) . ?
C16 C17 1.404(7) . ?
C16 C15A 1.405(6) . ?
C19A C19 1.402(6) . ?
C19A C15A 1.417(6) . ?
C19A C12 1.484(6) . ?
C18 C17 1.377(6) . ?
C18 C19 1.400(6) . ?
C18 H18 0.9300 . ?
C14 C13 1.330(7) . ?
C14 C15 1.474(7) . ?
C14 H14 0.9300 . ?
C12 C13 1.480(7) . ?
C15A C15 1.493(6) . ?
C13 C20 1.497(6) . ?
C2 C3 1.337(7) . ?
C2 H2 0.9300 . ?
C8A C8 1.406(6) . ?
C8A C4A 1.409(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C4A C5 1.402(6) . ?
C4A C4 1.492(6) . ?
C3 C4 1.477(6) . ?
C3 C9 1.495(6) . ?
C5 C6 1.393(7) . ?
C17 H17 0.9300 . ?
C8 C7 1.402(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C7 C6 1.375(8) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 H9D 0.9600 . ?
C9 H9E 0.9600 . ?
C9 H9F 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 H20D 0.9600 . ?
C20 H20E 0.9600 . ?
C20 H20F 0.9600 . ?
F2 C10 1.333(10) . ?
F3 C10 1.330(9) . ?
F1 C10 1.349(8) . ?

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
C19 S2 C21 103.0(2) . . ?
C10 S1 C5 102.0(3) . . ?
C16 O6 C22 117.6(4) . . ?
C8 O3 C11 118.3(4) . . ?
O1 C1 C2 118.8(4) . . ?
O1 C1 C8A 122.5(4) . . ?
C2 C1 C8A 118.6(4) . . ?
O6 C16 C17 122.5(4) . . ?
O6 C16 C15A 118.2(4) . . ?
C17 C16 C15A 119.3(4) . . ?
C19 C19A C15A 120.9(4) . . ?
C19 C19A C12 119.4(4) . . ?
C15A C19A C12 119.7(4) . . ?
F5 C21 F4 107.5(4) . . ?
F5 C21 F6 105.6(4) . . ?
F4 C21 F6 107.1(4) . . ?
F5 C21 S2 116.3(4) . . ?
F4 C21 S2 105.3(4) . . ?
F6 C21 S2 114.7(4) . . ?
C17 C18 C19 121.7(4) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C13 C14 C15 124.6(4) . . ?
C13 C14 H14 117.7 . . ?
C15 C14 H14 117.7 . . ?
O4 C12 C13 119.9(4) . . ?
O4 C12 C19A 119.7(4) . . ?
C13 C12 C19A 120.4(4) . . ?
C16 C15A C19A 119.3(4) . . ?
C16 C15A C15 121.7(4) . . ?
C19A C15A C15 118.9(4) . . ?
C14 C13 C12 118.5(4) . . ?
C14 C13 C20 124.4(4) . . ?
C12 C13 C20 117.1(4) . . ?
C3 C2 C1 123.6(4) . . ?
C3 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
C18 C19 C19A 118.1(4) . . ?
C18 C19 S2 122.3(3) . . ?
C19A C19 S2 119.6(3) . . ?
O5 C15 C14 118.7(4) . . ?
O5 C15 C15A 123.4(4) . . ?
C14 C15 C15A 117.9(4) . . ?
C8 C8A C4A 119.7(4) . . ?
C8 C8A C1 121.9(4) . . ?
C4A C8A C1 118.4(4) . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5 C4A C8A 121.1(4) . . ?
C5 C4A C4 119.1(4) . . ?
C8A C4A C4 119.8(4) . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 C9 124.4(4) . . ?
C4 C3 C9 116.7(4) . . ?
C6 C5 C4A 117.9(4) . . ?
C6 C5 S1 121.7(4) . . ?
C4A C5 S1 120.4(3) . . ?
O2 C4 C3 119.6(4) . . ?
O2 C4 C4A 120.6(4) . . ?
C3 C4 C4A 119.9(4) . . ?
C18 C17 C16 120.5(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
O3 C8 C7 123.3(4) . . ?
O3 C8 C8A 118.2(4) . . ?
C7 C8 C8A 118.5(4) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C7 C8 121.1(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C6 C5 121.6(5) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C9 H9D 109.5 . . ?
H9A C9 H9D 141.1 . . ?
H9B C9 H9D 56.3 . . ?
H9C C9 H9D 56.3 . . ?
C3 C9 H9E 109.5 . . ?
H9A C9 H9E 56.3 . . ?
H9B C9 H9E 141.1 . . ?
H9C C9 H9E 56.3 . . ?
H9D C9 H9E 109.5 . . ?
C3 C9 H9F 109.5 . . ?
H9A C9 H9F 56.3 . . ?
H9B C9 H9F 56.3 . . ?
H9C C9 H9F 141.1 . . ?
H9D C9 H9F 109.5 . . ?
H9E C9 H9F 109.5 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C20 H20D 109.5 . . ?
H20A C20 H20D 141.1 . . ?
H20B C20 H20D 56.3 . . ?
H20C C20 H20D 56.3 . . ?
C13 C20 H20E 109.5 . . ?
H20A C20 H20E 56.3 . . ?
H20B C20 H20E 141.1 . . ?
H20C C20 H20E 56.3 . . ?
H20D C20 H20E 109.5 . . ?
C13 C20 H20F 109.5 . . ?
H20A C20 H20F 56.3 . . ?
H20B C20 H20F 56.3 . . ?
H20C C20 H20F 141.1 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 109.5 . . ?
F3 C10 F2 104.7(7) . . ?
F3 C10 F1 108.5(7) . . ?
F2 C10 F1 106.2(6) . . ?
F3 C10 S1 114.9(6) . . ?
F2 C10 S1 116.2(6) . . ?
F1 C10 S1 105.9(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
C22 O6 C16 C17 -1.5(6) . . . . ?
C22 O6 C16 C15A 179.5(4) . . . . ?
C19 S2 C21 F5 -67.7(4) . . . . ?
C19 S2 C21 F4 173.5(4) . . . . ?
C19 S2 C21 F6 56.1(4) . . . . ?
C19 C19A C12 O4 -1.6(6) . . . . ?
C15A C19A C12 O4 177.2(4) . . . . ?
C19 C19A C12 C13 179.2(4) . . . . ?
C15A C19A C12 C13 -2.0(6) . . . . ?
O6 C16 C15A C19A -179.0(4) . . . . ?
C17 C16 C15A C19A 2.0(6) . . . . ?
O6 C16 C15A C15 1.8(6) . . . . ?
C17 C16 C15A C15 -177.2(4) . . . . ?
C19 C19A C15A C16 0.7(6) . . . . ?
C12 C19A C15A C16 -178.1(4) . . . . ?
C19 C19A C15A C15 179.9(4) . . . . ?
C12 C19A C15A C15 1.1(6) . . . . ?
C15 C14 C13 C12 0.0(8) . . . . ?
C15 C14 C13 C20 -178.2(5) . . . . ?
O4 C12 C13 C14 -177.8(5) . . . . ?
C19A C12 C13 C14 1.4(7) . . . . ?
O4 C12 C13 C20 0.6(7) . . . . ?
C19A C12 C13 C20 179.7(4) . . . . ?
O1 C1 C2 C3 -175.3(5) . . . . ?
C8A C1 C2 C3 5.3(7) . . . . ?
C17 C18 C19 C19A 3.0(7) . . . . ?
C17 C18 C19 S2 -176.4(4) . . . . ?
C15A C19A C19 C18 -3.1(6) . . . . ?
C12 C19A C19 C18 175.7(4) . . . . ?
C15A C19A C19 S2 176.3(3) . . . . ?
C12 C19A C19 S2 -4.9(6) . . . . ?
C21 S2 C19 C18 9.0(4) . . . . ?
C21 S2 C19 C19A -170.5(4) . . . . ?
C13 C14 C15 O5 178.7(5) . . . . ?
C13 C14 C15 C15A -0.9(8) . . . . ?
C16 C15A C15 O5 -0.1(8) . . . . ?
C19A C15A C15 O5 -179.2(5) . . . . ?
C16 C15A C15 C14 179.4(4) . . . . ?
C19A C15A C15 C14 0.2(6) . . . . ?
O1 C1 C8A C8 -6.7(7) . . . . ?
C2 C1 C8A C8 172.7(4) . . . . ?
O1 C1 C8A C4A 174.7(4) . . . . ?
C2 C1 C8A C4A -5.9(6) . . . . ?
C8 C8A C4A C5 0.8(7) . . . . ?
C1 C8A C4A C5 179.4(4) . . . . ?
C8 C8A C4A C4 -179.6(4) . . . . ?
C1 C8A C4A C4 -0.9(6) . . . . ?
C1 C2 C3 C4 2.5(7) . . . . ?
C1 C2 C3 C9 179.3(4) . . . . ?
C8A C4A C5 C6 1.9(7) . . . . ?
C4 C4A C5 C6 -177.7(4) . . . . ?
C8A C4A C5 S1 -178.2(3) . . . . ?
C4 C4A C5 S1 2.1(6) . . . . ?
C10 S1 C5 C6 -21.1(5) . . . . ?
C10 S1 C5 C4A 159.0(5) . . . . ?
C2 C3 C4 O2 169.3(5) . . . . ?
C9 C3 C4 O2 -7.8(7) . . . . ?
C2 C3 C4 C4A -9.5(6) . . . . ?
C9 C3 C4 C4A 173.5(4) . . . . ?
C5 C4A C4 O2 9.6(7) . . . . ?
C8A C4A C4 O2 -170.1(4) . . . . ?
C5 C4A C4 C3 -171.6(4) . . . . ?
C8A C4A C4 C3 8.7(6) . . . . ?
C19 C18 C17 C16 -0.4(7) . . . . ?
O6 C16 C17 C18 178.9(4) . . . . ?
C15A C16 C17 C18 -2.1(7) . . . . ?
C11 O3 C8 C7 3.2(8) . . . . ?
C11 O3 C8 C8A -177.5(4) . . . . ?
C4A C8A C8 O3 178.1(4) . . . . ?
C1 C8A C8 O3 -0.5(7) . . . . ?
C4A C8A C8 C7 -2.6(7) . . . . ?
C1 C8A C8 C7 178.8(4) . . . . ?
O3 C8 C7 C6 -178.9(5) . . . . ?
C8A C8 C7 C6 1.8(8) . . . . ?
C8 C7 C6 C5 1.0(8) . . . . ?
C4A C5 C6 C7 -2.8(7) . . . . ?
S1 C5 C6 C7 177.4(4) . . . . ?
C5 S1 C10 F3 -49.3(7) . . . . ?
C5 S1 C10 F2 73.5(6) . . . . ?
C5 S1 C10 F1 -169.0(5) . . . . ?

_refine_diff_density_max         3.194
_refine_diff_density_min         -1.219
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_shelx_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 1586326'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 O2 S'
_chemical_formula_sum            'C17 H12 O2 S'
_chemical_formula_weight         280.33

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.2227(6)
_cell_length_b                   8.4064(7)
_cell_length_c                   12.3348(9)
_cell_angle_alpha                75.046(7)
_cell_angle_beta                 76.516(7)
_cell_angle_gamma                66.783(8)
_cell_volume                     657.64(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    2322
_cell_measurement_theta_min      3.0860
_cell_measurement_theta_max      27.3460

_exptl_crystal_description       Sheet
_exptl_crystal_colour            'Dark Orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    0.243
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            7911
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.683
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2682
_reflns_number_gt                2090
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SuperFlip (Palatinus & Chapius, 2007)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0381P)²+0.0910P] 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         2682
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.33921(7) 0.18373(6) 0.26739(4) 0.03576(16) Uani 1 1 d . . . . .
O1 O 0.1032(2) -0.14167(19) 0.78427(11) 0.0495(4) Uani 1 1 d . . . . .
O2 O 0.2434(2) 0.34921(17) 0.44138(11) 0.0493(4) Uani 1 1 d . . . . .
C14 C 0.2661(3) 0.4234(3) -0.11481(16) 0.0487(5) Uani 1 1 d . . . . .
H14 H 0.154488 0.486711 -0.153038 0.058 Uiso 1 1 calc R U . . .
C5 C 0.3042(2) 0.0213(2) 0.38420(14) 0.0287(4) Uani 1 1 d . . . . .
C10 C 0.4143(3) 0.2066(2) 0.04132(14) 0.0355(4) Uani 1 1 d . . . . .
C9 C 0.3942(3) 0.0751(2) 0.14789(14) 0.0387(4) Uani 1 1 d . . . . .
H9A H 0.519799 -0.026246 0.152016 0.046 Uiso 1 1 calc R U . . .
H9B H 0.284873 0.035106 0.148679 0.046 Uiso 1 1 calc R U . . .
C8 C 0.2365(3) -0.2356(2) 0.56974(16) 0.0374(4) Uani 1 1 d . . . . .
H8 H 0.211887 -0.320296 0.630655 0.045 Uiso 1 1 calc R U . . .
C8A C 0.2127(2) -0.0722(2) 0.58734(14) 0.0307(4) Uani 1 1 d . . . . .
C15 C 0.2489(3) 0.3031(3) -0.01640(16) 0.0422(5) Uani 1 1 d . . . . .
H15 H 0.125279 0.286521 0.011477 0.051 Uiso 1 1 calc R U . . .
C4A C 0.2467(2) 0.0576(2) 0.49540(14) 0.0278(4) Uani 1 1 d . . . . .
C2 C 0.1265(3) 0.1370(3) 0.72127(16) 0.0432(5) Uani 1 1 d . . . . .
H2 H 0.091353 0.160875 0.794405 0.052 Uiso 1 1 calc R U . . .
C1 C 0.1454(3) -0.0347(3) 0.70469(15) 0.0365(4) Uani 1 1 d . . . . .
C6 C 0.3298(3) -0.1470(2) 0.37081(15) 0.0342(4) Uani 1 1 d . . . . .
H6 H 0.370335 -0.174725 0.298600 0.041 Uiso 1 1 calc R U . . .
C11 C 0.5958(3) 0.2359(3) -0.00083(16) 0.0419(5) Uani 1 1 d . . . . .
H11 H 0.707557 0.173782 0.037425 0.050 Uiso 1 1 calc R U . . .
C4 C 0.2182(3) 0.2307(2) 0.51727(15) 0.0339(4) Uani 1 1 d . . . . .
C7 C 0.2966(3) -0.2723(2) 0.46194(16) 0.0380(4) Uani 1 1 d . . . . .
H7 H 0.314965 -0.382925 0.450474 0.046 Uiso 1 1 calc R U . . .
C13 C 0.4478(4) 0.4500(3) -0.15648(17) 0.0492(5) Uani 1 1 d . . . . .
H13 H 0.459486 0.530439 -0.223030 0.059 Uiso 1 1 calc R U . . .
C3 C 0.1578(3) 0.2597(3) 0.63522(16) 0.0442(5) Uani 1 1 d . . . . .
H3 H 0.141162 0.368115 0.649690 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6122(3) 0.3567(3) -0.09912(17) 0.0471(5) Uani 1 1 d . . . . .
H12 H 0.734835 0.375189 -0.126713 0.057 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 C5 1.7581(17) . ?
S1 C9 1.8167(18) . ?
O1 C1 1.219(2) . ?
O2 C4 1.218(2) . ?
C14 C13 1.376(3) . ?
C14 C15 1.381(3) . ?
C14 H14 0.9300 . ?
C5 C6 1.401(2) . ?
C5 C4A 1.413(2) . ?
C10 C11 1.386(3) . ?
C10 C15 1.388(2) . ?
C10 C9 1.503(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 C7 1.374(3) . ?
C8 C8A 1.383(2) . ?
C8 H8 0.9300 . ?
C8A C4A 1.407(2) . ?
C8A C1 1.489(2) . ?
C15 H15 0.9300 . ?
C4A C4 1.474(2) . ?
C2 C3 1.322(3) . ?
C2 C1 1.459(3) . ?
C2 H2 0.9300 . ?
C6 C7 1.376(2) . ?
C6 H6 0.9300 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C4 C3 1.473(3) . ?
C7 H7 0.9300 . ?
C13 C12 1.377(3) . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?

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
C5 S1 C9 102.66(8) . . ?
C13 C14 C15 120.22(19) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C6 C5 C4A 117.69(15) . . ?
C6 C5 S1 121.64(13) . . ?
C4A C5 S1 120.66(13) . . ?
C11 C10 C15 118.56(17) . . ?
C11 C10 C9 121.25(17) . . ?
C15 C10 C9 120.18(17) . . ?
C10 C9 S1 107.58(12) . . ?
C10 C9 H9A 110.2 . . ?
S1 C9 H9A 110.2 . . ?
C10 C9 H9B 110.2 . . ?
S1 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C7 C8 C8A 119.78(16) . . ?
C7 C8 H8 120.1 . . ?
C8A C8 H8 120.1 . . ?
C8 C8A C4A 120.45(16) . . ?
C8 C8A C1 118.83(16) . . ?
C4A C8A C1 120.70(16) . . ?
C14 C15 C10 120.65(18) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C8A C4A C5 119.79(15) . . ?
C8A C4A C4 118.94(15) . . ?
C5 C4A C4 121.26(15) . . ?
C3 C2 C1 121.84(17) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
O1 C1 C2 120.70(17) . . ?
O1 C1 C8A 121.60(17) . . ?
C2 C1 C8A 117.69(16) . . ?
C7 C6 C5 121.56(16) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C12 C11 C10 120.59(18) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
O2 C4 C3 119.37(16) . . ?
O2 C4 C4A 122.23(16) . . ?
C3 C4 C4A 118.41(16) . . ?
C8 C7 C6 120.70(17) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C14 C13 C12 119.66(19) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C2 C3 C4 122.35(18) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C13 C12 C11 120.30(19) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_shelx_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 1586329'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_vrf_PLAT230_shelx               
;
PROBLEM: Hirshfeld Test Diff for    S1     --  C9      ..        9.8 s.u.  
RESPONSE: Possible disordered CF3 group, but all atempts to model it has failed.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H5 F3 O2 S'
_chemical_formula_sum            'C11 H5 F3 O2 S'
_chemical_formula_weight         258.21

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.2151(6)
_cell_length_b                   7.8797(2)
_cell_length_c                   7.1525(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.718(3)
_cell_angle_gamma                90
_cell_volume                     1073.14(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14987
_cell_measurement_theta_min      2.9440
_cell_measurement_theta_max      28.1180

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.597
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.164
_exptl_absorpt_coefficient_mu    0.328
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            42253
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.798
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2193
_reflns_number_gt                1914
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SuperFlip (Palatinus & Chapius, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0869P)²+0.8313P] 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         2193
_refine_ls_number_parameters     152
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1866
_refine_ls_wR_factor_gt          0.1802
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_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 0.8261(3) 0.6160(2) 0.1931(3) 0.0771(4) Uani 1 1 d . U . . .
O2 O 0.56822(14) 0.1619(4) -0.1546(4) 0.1017(9) Uani 1 1 d . . . . .
O1 O 0.69732(16) 0.7264(3) 0.0933(5) 0.1075(10) Uani 1 1 d . . . . .
C8A C 0.67346(13) 0.2841(3) -0.0059(3) 0.0473(6) Uani 1 1 d . . . . .
C4 C 0.67248(17) 0.5970(4) 0.0216(5) 0.0646(8) Uani 1 1 d . . . . .
C6 C 0.81049(15) 0.2651(4) 0.1666(4) 0.0542(6) Uani 1 1 d . . . . .
H8 H 0.8568 0.2569 0.2234 0.065 Uiso 1 1 calc R U . . .
C4A C 0.70991(13) 0.4339(3) 0.0482(3) 0.0445(5) Uani 1 1 d . . . . .
C8 C 0.70480(16) 0.1289(3) 0.0295(4) 0.0565(7) Uani 1 1 d . . . . .
H6 H 0.6800 0.0301 -0.0059 0.068 Uiso 1 1 calc R U . . .
C1 C 0.60046(16) 0.2916(5) -0.1052(4) 0.0657(8) Uani 1 1 d . . . . .
C2 C 0.56907(17) 0.4585(6) -0.1465(5) 0.0808(10) Uani 1 1 d . . . . .
H3 H 0.5245 0.4658 -0.2149 0.097 Uiso 1 1 calc R U . . .
C7 C 0.77271(17) 0.1199(3) 0.1171(4) 0.0595(7) Uani 1 1 d . . . . .
H7 H 0.7935 0.0144 0.1433 0.071 Uiso 1 1 calc R U . . .
C5 C 0.77991(14) 0.4241(3) 0.1324(3) 0.0470(6) Uani 1 1 d . . . . .
C3 C 0.60239(19) 0.5985(5) -0.0891(6) 0.0808(10) Uani 1 1 d . . . . .
H2 H 0.5808 0.7023 -0.1198 0.097 Uiso 1 1 calc R U . . .
F1 F 0.93343(19) 0.4603(6) 0.0821(9) 0.191(2) Uani 1 1 d . . . . .
F2 F 0.95257(18) 0.6890(6) 0.2434(8) 0.217(2) Uani 1 1 d . . . . .
C9 C 0.9160(3) 0.5457(8) 0.2247(11) 0.128(2) Uani 1 1 d . U . . .
F3 F 0.93152(18) 0.4539(6) 0.3836(7) 0.1819(18) 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 C5 1.777(2) . ?
S1 C9 1.800(7) . ?
O2 C1 1.223(4) . ?
O1 C4 1.211(4) . ?
C8A C8 1.372(4) . ?
C8A C4A 1.400(3) . ?
C8A C1 1.486(4) . ?
C4 C3 1.468(5) . ?
C4 C4A 1.473(4) . ?
C6 C7 1.375(4) . ?
C6 C5 1.392(4) . ?
C6 H8 0.9300 . ?
C4A C5 1.400(4) . ?
C8 C7 1.372(4) . ?
C8 H6 0.9300 . ?
C1 C2 1.460(5) . ?
C2 C3 1.313(5) . ?
C2 H3 0.9300 . ?
C7 H7 0.9300 . ?
C3 H2 0.9300 . ?
F1 C9 1.303(8) . ?
F2 C9 1.327(6) . ?
C9 F3 1.346(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
C5 S1 C9 102.0(2) . . ?
C8 C8A C4A 120.6(2) . . ?
C8 C8A C1 119.1(2) . . ?
C4A C8A C1 120.3(2) . . ?
O1 C4 C3 120.2(3) . . ?
O1 C4 C4A 121.5(3) . . ?
C3 C4 C4A 118.3(3) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H8 119.7 . . ?
C5 C6 H8 119.7 . . ?
C8A C4A C5 119.3(2) . . ?
C8A C4A C4 118.8(2) . . ?
C5 C4A C4 121.8(2) . . ?
C7 C8 C8A 119.9(2) . . ?
C7 C8 H6 120.1 . . ?
C8A C8 H6 120.1 . . ?
O2 C1 C2 121.0(3) . . ?
O2 C1 C8A 120.9(3) . . ?
C2 C1 C8A 118.0(3) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H3 119.2 . . ?
C1 C2 H3 119.2 . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C6 C5 C4A 118.9(2) . . ?
C6 C5 S1 122.6(2) . . ?
C4A C5 S1 118.53(19) . . ?
C2 C3 C4 122.4(3) . . ?
C2 C3 H2 118.8 . . ?
C4 C3 H2 118.8 . . ?
F1 C9 F2 109.3(6) . . ?
F1 C9 F3 109.4(6) . . ?
F2 C9 F3 108.5(5) . . ?
F1 C9 S1 113.9(4) . . ?
F2 C9 S1 103.7(5) . . ?
F3 C9 S1 111.8(5) . . ?

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_shelx_CCDC10
_database_code_depnum_ccdc_archive 'CCDC 1586327'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 O4 S'
_chemical_formula_sum            'C21 H14 O4 S'
_chemical_formula_weight         362.38

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.1466(18)
_cell_length_b                   12.4232(17)
_cell_length_c                   18.979(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3335.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2963
_cell_measurement_theta_min      2.4130
_cell_measurement_theta_max      26.2600

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.471
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.219
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            15833
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.431
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3410
_reflns_number_gt                2303
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SuperFlip (Palatinus & Chapius, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0435P)²+1.0272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3410
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.74630(4) 0.48774(5) 0.16764(3) 0.03846(19) Uani 1 1 d . . . . .
O4 O 0.80180(10) 0.39364(13) 0.15392(9) 0.0513(5) Uani 1 1 d . . . . .
O2 O 0.74746(11) 0.41732(15) 0.01458(9) 0.0562(5) Uani 1 1 d . . . . .
O3 O 0.73948(11) 0.52157(14) 0.23989(9) 0.0536(5) Uani 1 1 d . . . . .
O1 O 0.38535(10) 0.33841(14) -0.01580(9) 0.0554(5) Uani 1 1 d . . . . .
C3 C 0.46292(16) 0.49631(19) 0.16681(14) 0.0465(6) Uani 1 1 d . . . . .
H3 H 0.4176 0.5249 0.1969 0.056 Uiso 1 1 calc R U . . .
C5A C 0.53905(15) 0.28055(17) -0.04394(12) 0.0370(5) Uani 1 1 d . . . . .
C12 C 0.88707(14) 0.62782(17) 0.13253(12) 0.0366(5) Uani 1 1 d . . . . .
C7 C 0.67079(19) 0.1712(2) -0.12450(14) 0.0576(7) Uani 1 1 d . . . . .
H7 H 0.7149 0.1339 -0.1514 0.069 Uiso 1 1 calc R U . . .
C4A C 0.50356(14) 0.40078(17) 0.06128(12) 0.0353(5) Uani 1 1 d . . . . .
C2 C 0.55808(16) 0.50678(18) 0.18233(13) 0.0422(6) Uani 1 1 d . . . . .
H2 H 0.5762 0.5408 0.2238 0.051 Uiso 1 1 calc R U . . .
C8A C 0.63564(14) 0.29788(17) -0.03319(11) 0.0359(5) Uani 1 1 d . . . . .
C7A C 0.60048(13) 0.41454(16) 0.07468(11) 0.0325(5) Uani 1 1 d . . . . .
C10 C 0.46957(15) 0.33989(18) -0.00137(12) 0.0399(6) Uani 1 1 d . . . . .
C15 C 1.07503(17) 0.6743(2) 0.15902(15) 0.0530(7) Uani 1 1 d . . . . .
H15 H 1.1382 0.6891 0.1683 0.064 Uiso 1 1 calc R U . . .
C1 C 0.62670(14) 0.46761(17) 0.13731(12) 0.0349(5) Uani 1 1 d . . . . .
C9 C 0.66879(14) 0.37858(18) 0.01924(12) 0.0373(5) Uani 1 1 d . . . . .
C17 C 0.91188(16) 0.69077(18) 0.18968(12) 0.0427(6) Uani 1 1 d . . . . .
H17 H 0.8653 0.7175 0.2195 0.051 Uiso 1 1 calc R U . . .
C16 C 1.00611(17) 0.7140(2) 0.20266(14) 0.0505(6) Uani 1 1 d . . . . .
H16 H 1.0226 0.7567 0.2410 0.061 Uiso 1 1 calc R U . . .
C14 C 1.05116(17) 0.6129(2) 0.10204(15) 0.0548(7) Uani 1 1 d . . . . .
H14 H 1.0980 0.5870 0.0721 0.066 Uiso 1 1 calc R U . . .
C6 C 0.57575(19) 0.1544(2) -0.13559(14) 0.0549(7) Uani 1 1 d . . . . .
H6 H 0.5561 0.1062 -0.1701 0.066 Uiso 1 1 calc R U . . .
C13 C 0.95736(17) 0.58928(19) 0.08883(13) 0.0479(6) Uani 1 1 d . . . . .
H13 H 0.9414 0.5471 0.0501 0.057 Uiso 1 1 calc R U . . .
C8 C 0.70132(17) 0.24304(19) -0.07374(13) 0.0471(6) Uani 1 1 d . . . . .
H8 H 0.7656 0.2545 -0.0668 0.056 Uiso 1 1 calc R U . . .
C4 C 0.43627(15) 0.44361(18) 0.10692(14) 0.0432(6) Uani 1 1 d . . . . .
H4 H 0.3724 0.4362 0.0965 0.052 Uiso 1 1 calc R U . . .
C5 C 0.50971(18) 0.2086(2) -0.09583(13) 0.0489(6) Uani 1 1 d . . . . .
H5 H 0.4456 0.1971 -0.1036 0.059 Uiso 1 1 calc R U . . .
C11 C 0.78528(15) 0.60153(18) 0.11798(13) 0.0444(6) Uani 1 1 d . . . . .
H11A H 0.7774 0.5868 0.0681 0.053 Uiso 1 1 calc R U . . .
H11B H 0.7464 0.6633 0.1297 0.053 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 O4 1.4320(16) . ?
S1 O3 1.4376(17) . ?
S1 C11 1.786(2) . ?
S1 C1 1.805(2) . ?
O2 C9 1.216(2) . ?
O1 C10 1.223(2) . ?
C3 C4 1.365(3) . ?
C3 C2 1.384(3) . ?
C3 H3 0.9300 . ?
C5A C5 1.394(3) . ?
C5A C8A 1.398(3) . ?
C5A C10 1.470(3) . ?
C12 C13 1.381(3) . ?
C12 C17 1.383(3) . ?
C12 C11 1.502(3) . ?
C7 C6 1.377(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9300 . ?
C4A C4 1.393(3) . ?
C4A C7A 1.405(3) . ?
C4A C10 1.489(3) . ?
C2 C1 1.382(3) . ?
C2 H2 0.9300 . ?
C8A C8 1.386(3) . ?
C8A C9 1.488(3) . ?
C7A C1 1.409(3) . ?
C7A C9 1.497(3) . ?
C15 C14 1.366(4) . ?
C15 C16 1.371(4) . ?
C15 H15 0.9300 . ?
C17 C16 1.386(3) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C14 C13 1.382(3) . ?
C14 H14 0.9300 . ?
C6 C5 1.377(3) . ?
C6 H6 0.9300 . ?
C13 H13 0.9300 . ?
C8 H8 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
O4 S1 O3 116.67(10) . . ?
O4 S1 C11 112.39(11) . . ?
O3 S1 C11 107.01(11) . . ?
O4 S1 C1 110.06(10) . . ?
O3 S1 C1 106.37(10) . . ?
C11 S1 C1 103.34(10) . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C5A C8A 119.5(2) . . ?
C5 C5A C10 120.7(2) . . ?
C8A C5A C10 119.7(2) . . ?
C13 C12 C17 119.0(2) . . ?
C13 C12 C11 120.3(2) . . ?
C17 C12 C11 120.7(2) . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C4 C4A C7A 120.5(2) . . ?
C4 C4A C10 118.04(19) . . ?
C7A C4A C10 121.43(19) . . ?
C1 C2 C3 121.2(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C8 C8A C5A 119.9(2) . . ?
C8 C8A C9 119.42(19) . . ?
C5A C8A C9 120.6(2) . . ?
C4A C7A C1 117.81(19) . . ?
C4A C7A C9 117.80(19) . . ?
C1 C7A C9 124.25(18) . . ?
O1 C10 C5A 121.4(2) . . ?
O1 C10 C4A 120.1(2) . . ?
C5A C10 C4A 118.53(18) . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C2 C1 C7A 120.10(19) . . ?
C2 C1 S1 114.37(17) . . ?
C7A C1 S1 125.50(16) . . ?
O2 C9 C8A 120.4(2) . . ?
O2 C9 C7A 121.6(2) . . ?
C8A C9 C7A 117.88(18) . . ?
C12 C17 C16 120.1(2) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C7 C8 C8A 119.7(2) . . ?
C7 C8 H8 120.2 . . ?
C8A C8 H8 120.2 . . ?
C3 C4 C4A 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C4A C4 H4 119.6 . . ?
C6 C5 C5A 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
C5A C5 H5 120.0 . . ?
C12 C11 S1 111.78(15) . . ?
C12 C11 H11A 109.3 . . ?
S1 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
S1 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.049

