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

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

data_151118A
_database_code_depnum_ccdc_archive 'CCDC 1547742'
_audit_update_record             
;
2017-05-04 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 F N O5 S'
_chemical_formula_weight         315.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

_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+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   10.0438(9)
_cell_length_b                   10.0438(9)
_cell_length_c                   29.020(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2927.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5250
_cell_measurement_theta_min      2.565
_cell_measurement_theta_max      23.265

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.252
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19394
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         27.744
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3432
_reflns_number_gt                2492
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    1.000

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0633P)²+0.1934P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0018(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 833 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.93(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3432
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.3106(3) 0.8386(3) 0.14736(10) 0.0433(6) Uani 1 1 d . . . . .
C2 C 0.1914(3) 0.8523(3) 0.17034(11) 0.0559(8) Uani 1 1 d . . . . .
H2 H 0.1457 0.9327 0.1688 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1383(3) 0.7478(3) 0.19581(12) 0.0591(8) Uani 1 1 d . . . . .
H3 H 0.0573 0.7570 0.2110 0.071 Uiso 1 1 calc R U . . .
C4 C 0.2078(3) 0.6318(3) 0.19797(11) 0.0545(8) Uani 1 1 d . . . . .
C5 C 0.3262(4) 0.6139(4) 0.17648(12) 0.0623(9) Uani 1 1 d . . . . .
H5 H 0.3713 0.5333 0.1785 0.075 Uiso 1 1 calc R U . . .
C6 C 0.3778(3) 0.7189(3) 0.15157(11) 0.0571(8) Uani 1 1 d . . . . .
H6 H 0.4600 0.7090 0.1372 0.069 Uiso 1 1 calc R U . . .
C7 C 0.3642(3) 0.9496(3) 0.11843(10) 0.0429(6) Uani 1 1 d . . . . .
C8 C 0.3158(3) 0.9599(3) 0.07108(10) 0.0471(7) Uani 1 1 d . . . . .
C9 C 0.4551(3) 1.0370(3) 0.13477(10) 0.0457(6) Uani 1 1 d . . . . .
C10 C 0.5063(3) 1.0329(4) 0.18335(11) 0.0606(9) Uani 1 1 d . . . . .
H10A H 0.4587 0.9640 0.2000 0.073 Uiso 1 1 calc R U . . .
H10B H 0.4862 1.1173 0.1981 0.073 Uiso 1 1 calc R U . . .
C11 C 0.6541(4) 1.0068(4) 0.18779(14) 0.0709(10) Uani 1 1 d . . . . .
H11A H 0.6711 0.9709 0.2182 0.085 Uiso 1 1 calc R U . . .
H11B H 0.6787 0.9389 0.1656 0.085 Uiso 1 1 calc R U . . .
C12 C 0.7433(4) 1.1252(4) 0.18073(17) 0.0852(12) Uani 1 1 d . . . . .
H12A H 0.7178 1.1949 0.2021 0.102 Uiso 1 1 calc R U . . .
H12B H 0.8344 1.0999 0.1876 0.102 Uiso 1 1 calc R U . . .
C13 C 0.1672(5) 0.8726(5) 0.01591(13) 0.0979(16) Uani 1 1 d . . . . .
H13A H 0.2283 0.8337 -0.0057 0.147 Uiso 1 1 calc R U . . .
H13B H 0.1506 0.9636 0.0075 0.147 Uiso 1 1 calc R U . . .
H13C H 0.0851 0.8238 0.0155 0.147 Uiso 1 1 calc R U . . .
F1 F 0.1547(2) 0.5297(2) 0.22262(7) 0.0785(7) Uani 1 1 d . . . . .
N1 N 0.5054(3) 1.1339(3) 0.10605(9) 0.0574(7) Uani 1 1 d . . . . .
H1 H 0.4778 1.1315 0.0766 0.086 Uiso 1 1 d R U . . .
O1 O 0.5630(3) 1.3299(3) 0.15532(11) 0.0903(9) Uani 1 1 d . . . . .
O2 O 0.6396(3) 1.3117(3) 0.07530(10) 0.0894(9) Uani 1 1 d . . . . .
O3 O 0.3508(2) 1.0412(2) 0.04264(7) 0.0600(6) Uani 1 1 d . . . . .
O4 O 0.2240(2) 0.8677(2) 0.06162(7) 0.0666(7) Uani 1 1 d . . . . .
O5 O 0.7367(3) 1.1772(3) 0.13363(11) 0.0820(8) Uani 1 1 d . . . . .
S1 S 0.60963(9) 1.25171(9) 0.11809(4) 0.0649(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.377(4) . ?
C1 C6 1.384(4) . ?
C1 C7 1.496(4) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(5) . ?
C4 F1 1.359(3) . ?
C5 C6 1.380(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C9 1.353(4) . ?
C7 C8 1.461(4) . ?
C8 O3 1.213(3) . ?
C8 O4 1.334(4) . ?
C9 N1 1.377(4) . ?
C9 C10 1.501(5) . ?
C10 C11 1.513(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.502(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O5 1.465(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O4 1.445(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 S1 1.618(3) . ?
N1 H1 0.8999 . ?
O1 S1 1.415(3) . ?
O2 S1 1.413(3) . ?
O5 S1 1.547(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.9(3) . . ?
C2 C1 C7 120.7(3) . . ?
C6 C1 C7 121.4(3) . . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 122.9(3) . . ?
C5 C4 F1 119.1(3) . . ?
C3 C4 F1 118.0(3) . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C9 C7 C8 120.6(3) . . ?
C9 C7 C1 122.0(3) . . ?
C8 C7 C1 117.4(2) . . ?
O3 C8 O4 121.8(3) . . ?
O3 C8 C7 126.2(3) . . ?
O4 C8 C7 112.0(2) . . ?
C7 C9 N1 119.6(3) . . ?
C7 C9 C10 122.9(3) . . ?
N1 C9 C10 117.5(3) . . ?
C9 C10 C11 114.9(3) . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C10 115.9(3) . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
O5 C12 C11 112.5(3) . . ?
O5 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
O5 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 N1 S1 128.6(2) . . ?
C9 N1 H1 116.3 . . ?
S1 N1 H1 115.1 . . ?
C8 O4 C13 116.0(3) . . ?
C12 O5 S1 118.8(3) . . ?
O2 S1 O1 120.33(19) . . ?
O2 S1 O5 106.67(18) . . ?
O1 S1 O5 108.61(19) . . ?
O2 S1 N1 105.08(16) . . ?
O1 S1 N1 110.88(16) . . ?
O5 S1 N1 104.04(15) . . ?

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
C6 C1 C2 C3 -1.9(5) . . . . ?
C7 C1 C2 C3 177.4(3) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C2 C3 C4 F1 -179.4(3) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
F1 C4 C5 C6 179.8(3) . . . . ?
C4 C5 C6 C1 -1.5(5) . . . . ?
C2 C1 C6 C5 2.3(5) . . . . ?
C7 C1 C6 C5 -177.0(3) . . . . ?
C2 C1 C7 C9 96.5(4) . . . . ?
C6 C1 C7 C9 -84.2(4) . . . . ?
C2 C1 C7 C8 -84.3(3) . . . . ?
C6 C1 C7 C8 95.0(4) . . . . ?
C9 C7 C8 O3 1.1(5) . . . . ?
C1 C7 C8 O3 -178.1(3) . . . . ?
C9 C7 C8 O4 -178.3(3) . . . . ?
C1 C7 C8 O4 2.5(4) . . . . ?
C8 C7 C9 N1 -2.0(4) . . . . ?
C1 C7 C9 N1 177.2(3) . . . . ?
C8 C7 C9 C10 178.7(3) . . . . ?
C1 C7 C9 C10 -2.1(5) . . . . ?
C7 C9 C10 C11 117.5(4) . . . . ?
N1 C9 C10 C11 -61.8(4) . . . . ?
C9 C10 C11 C12 80.9(4) . . . . ?
C10 C11 C12 O5 -64.9(5) . . . . ?
C7 C9 N1 S1 177.4(2) . . . . ?
C10 C9 N1 S1 -3.2(4) . . . . ?
O3 C8 O4 C13 -1.3(5) . . . . ?
C7 C8 O4 C13 178.2(3) . . . . ?
C11 C12 O5 S1 71.8(4) . . . . ?
C12 O5 S1 O2 169.2(3) . . . . ?
C12 O5 S1 O1 38.1(3) . . . . ?
C12 O5 S1 N1 -80.0(3) . . . . ?
C9 N1 S1 O2 173.0(3) . . . . ?
C9 N1 S1 O1 -55.5(3) . . . . ?
C9 N1 S1 O5 61.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.90 1.85 2.582(3) 137.0 .
C13 H13C F1 0.96 2.40 3.206(5) 141.3 3_554
C10 H10B O1 0.97 2.59 3.144(5) 116.6 .
C10 H10A F1 0.97 2.55 3.336(4) 138.7 8_665
C10 H10A F1 0.97 2.55 3.336(4) 138.7 8_665
C10 H10B O1 0.97 2.59 3.144(5) 116.6 .
C13 H13C F1 0.96 2.40 3.206(5) 141.3 3_554
N1 H1 O3 0.90 1.85 2.582(3) 137.0 .

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.042

_shelxl_version_number           2014/6

