# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

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

data_mo_71017a
_audit_block_doi                 10.5517/ccdc.csd.cc1q3xyp
_database_code_depnum_ccdc_archive 'CCDC 1582703'
_audit_update_record             
;
2017-10-29 deposited with the CCDC.
2017-11-28 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         ?
_chemical_formula_sum            'C16 H13 F O4 S'
_chemical_formula_weight         320.32

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                   7.070(2)
_cell_length_b                   9.812(3)
_cell_length_c                   10.560(3)
_cell_angle_alpha                94.473(5)
_cell_angle_beta                 100.927(5)
_cell_angle_gamma                92.984(5)
_cell_volume                     715.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    2191
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.62

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5011
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.740
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3073
_reflns_number_gt                2488
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0811P)²+0.3286P] 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         3073
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1552
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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 0.14502(8) 0.01721(6) 0.72031(6) 0.0297(2) Uani 1 1 d . . . . .
O1 O -0.0124(2) 0.14327(15) 0.97097(16) 0.0269(4) Uani 1 1 d . . . . .
O2 O -0.3059(2) 0.21975(18) 0.9117(2) 0.0372(4) Uani 1 1 d . . . . .
O3 O -0.0569(3) 0.0397(2) 0.70291(18) 0.0401(5) Uani 1 1 d . . . . .
O4 O 0.2039(3) -0.11803(18) 0.6893(2) 0.0434(5) Uani 1 1 d . . . . .
F1 F 0.4946(4) 0.3846(2) 0.4080(2) 0.0886(9) Uani 1 1 d . . . . .
C1 C -0.1333(3) 0.2343(2) 0.9166(2) 0.0263(5) Uani 1 1 d . . . . .
C2 C -0.0167(3) 0.3435(2) 0.8729(2) 0.0249(5) Uani 1 1 d . . . . .
C3 C -0.0756(4) 0.4615(2) 0.8169(2) 0.0314(5) Uani 1 1 d . . . . .
H3 H -0.2067 0.4794 0.7966 0.038 Uiso 1 1 calc R U . . .
C4 C 0.0685(4) 0.5519(2) 0.7921(2) 0.0351(6) Uani 1 1 d . . . . .
H4 H 0.0354 0.6345 0.7568 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2601(4) 0.5214(2) 0.8190(2) 0.0324(5) Uani 1 1 d . . . . .
H5 H 0.3544 0.5829 0.7992 0.039 Uiso 1 1 calc R U . . .
C6 C 0.3178(3) 0.4022(2) 0.8746(2) 0.0280(5) Uani 1 1 d . . . . .
H6 H 0.4486 0.3830 0.8936 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1742(3) 0.3132(2) 0.9006(2) 0.0231(4) Uani 1 1 d . . . . .
C8 C 0.1873(3) 0.1795(2) 0.9622(2) 0.0238(5) Uani 1 1 d . . . . .
C9 C 0.2603(3) 0.0614(2) 0.8850(2) 0.0258(5) Uani 1 1 d . . . . .
H9A H 0.2516 -0.0206 0.9316 0.031 Uiso 1 1 calc R U . . .
H9B H 0.3975 0.0834 0.8865 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3064(4) 0.1915(2) 1.0998(2) 0.0308(5) Uani 1 1 d . . . . .
H10A H 0.2610 0.2642 1.1516 0.046 Uiso 1 1 calc R U . . .
H10B H 0.4412 0.2124 1.0974 0.046 Uiso 1 1 calc R U . . .
H10C H 0.2927 0.1055 1.1377 0.046 Uiso 1 1 calc R U . . .
C11 C 0.2531(4) 0.1324(2) 0.6302(2) 0.0306(5) Uani 1 1 d . . . . .
C12 C 0.4411(4) 0.1175(3) 0.6148(3) 0.0391(6) Uani 1 1 d . . . . .
H12 H 0.5123 0.0490 0.6549 0.047 Uiso 1 1 calc R U . . .
C13 C 0.5237(5) 0.2039(3) 0.5400(3) 0.0519(8) Uani 1 1 d . . . . .
H13 H 0.6511 0.1951 0.5281 0.062 Uiso 1 1 calc R U . . .
C14 C 0.4162(6) 0.3018(3) 0.4842(3) 0.0544(9) Uani 1 1 d . . . . .
C15 C 0.2294(6) 0.3215(3) 0.4994(3) 0.0548(9) Uani 1 1 d . . . . .
H15 H 0.1605 0.3918 0.4606 0.066 Uiso 1 1 calc R U . . .
C16 C 0.1469(5) 0.2339(3) 0.5738(3) 0.0431(6) Uani 1 1 d . . . . .
H16 H 0.0198 0.2435 0.5858 0.052 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 1.4354(19) . ?
S1 O4 1.4433(19) . ?
S1 C11 1.766(2) . ?
S1 C9 1.785(2) . ?
O1 C1 1.353(3) . ?
O1 C8 1.460(2) . ?
O2 C1 1.212(3) . ?
F1 C14 1.357(3) . ?
C1 C2 1.474(3) . ?
C2 C7 1.379(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.384(4) . ?
C5 C6 1.395(3) . ?
C6 C7 1.385(3) . ?
C7 C8 1.508(3) . ?
C8 C10 1.527(3) . ?
C8 C9 1.532(3) . ?
C11 C16 1.382(4) . ?
C11 C12 1.384(4) . ?
C12 C13 1.382(4) . ?
C13 C14 1.357(5) . ?
C14 C15 1.382(5) . ?
C15 C16 1.387(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 119.45(12) . . ?
O3 S1 C11 108.14(12) . . ?
O4 S1 C11 108.01(12) . . ?
O3 S1 C9 110.29(11) . . ?
O4 S1 C9 104.74(11) . . ?
C11 S1 C9 105.32(11) . . ?
C1 O1 C8 111.52(16) . . ?
O2 C1 O1 121.3(2) . . ?
O2 C1 C2 130.5(2) . . ?
O1 C1 C2 108.18(19) . . ?
C7 C2 C3 122.7(2) . . ?
C7 C2 C1 108.16(18) . . ?
C3 C2 C1 129.1(2) . . ?
C2 C3 C4 116.9(2) . . ?
C5 C4 C3 120.6(2) . . ?
C4 C5 C6 122.1(2) . . ?
C7 C6 C5 117.1(2) . . ?
C2 C7 C6 120.6(2) . . ?
C2 C7 C8 108.87(18) . . ?
C6 C7 C8 130.5(2) . . ?
O1 C8 C7 103.16(16) . . ?
O1 C8 C10 107.17(18) . . ?
C7 C8 C10 114.08(19) . . ?
O1 C8 C9 108.45(17) . . ?
C7 C8 C9 115.77(18) . . ?
C10 C8 C9 107.69(18) . . ?
C8 C9 S1 118.91(16) . . ?
C16 C11 C12 121.1(2) . . ?
C16 C11 S1 119.5(2) . . ?
C12 C11 S1 119.4(2) . . ?
C13 C12 C11 119.6(3) . . ?
C14 C13 C12 118.3(3) . . ?
C13 C14 F1 118.6(3) . . ?
C13 C14 C15 123.7(3) . . ?
F1 C14 C15 117.6(3) . . ?
C14 C15 C16 117.6(3) . . ?
C11 C16 C15 119.6(3) . . ?

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
C8 O1 C1 O2 178.3(2) . . . . ?
C8 O1 C1 C2 -2.9(2) . . . . ?
O2 C1 C2 C7 179.9(3) . . . . ?
O1 C1 C2 C7 1.1(3) . . . . ?
O2 C1 C2 C3 1.8(4) . . . . ?
O1 C1 C2 C3 -177.0(2) . . . . ?
C7 C2 C3 C4 -1.7(4) . . . . ?
C1 C2 C3 C4 176.2(2) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C4 C5 C6 C7 0.9(4) . . . . ?
C3 C2 C7 C6 0.9(4) . . . . ?
C1 C2 C7 C6 -177.3(2) . . . . ?
C3 C2 C7 C8 179.2(2) . . . . ?
C1 C2 C7 C8 1.0(3) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
C5 C6 C7 C8 -178.4(2) . . . . ?
C1 O1 C8 C7 3.3(2) . . . . ?
C1 O1 C8 C10 124.04(19) . . . . ?
C1 O1 C8 C9 -120.0(2) . . . . ?
C2 C7 C8 O1 -2.5(2) . . . . ?
C6 C7 C8 O1 175.5(2) . . . . ?
C2 C7 C8 C10 -118.4(2) . . . . ?
C6 C7 C8 C10 59.7(3) . . . . ?
C2 C7 C8 C9 115.8(2) . . . . ?
C6 C7 C8 C9 -66.2(3) . . . . ?
O1 C8 C9 S1 62.5(2) . . . . ?
C7 C8 C9 S1 -52.8(2) . . . . ?
C10 C8 C9 S1 178.16(15) . . . . ?
O3 S1 C9 C8 -33.3(2) . . . . ?
O4 S1 C9 C8 -163.08(16) . . . . ?
C11 S1 C9 C8 83.11(18) . . . . ?
O3 S1 C11 C16 8.3(2) . . . . ?
O4 S1 C11 C16 138.9(2) . . . . ?
C9 S1 C11 C16 -109.6(2) . . . . ?
O3 S1 C11 C12 -170.2(2) . . . . ?
O4 S1 C11 C12 -39.6(2) . . . . ?
C9 S1 C11 C12 71.9(2) . . . . ?
C16 C11 C12 C13 -1.1(4) . . . . ?
S1 C11 C12 C13 177.4(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 F1 -178.3(3) . . . . ?
C12 C13 C14 C15 1.0(5) . . . . ?
C13 C14 C15 C16 -1.4(5) . . . . ?
F1 C14 C15 C16 177.9(3) . . . . ?
C12 C11 C16 C15 0.6(4) . . . . ?
S1 C11 C16 C15 -177.8(2) . . . . ?
C14 C15 C16 C11 0.5(4) . . . . ?

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.089



