# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_haf4760
_database_code_depnum_ccdc_archive 'CCDC 1973261'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2021-06-01 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 F5 N O4 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         341.30
_chemical_absolute_configuration .

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   13.4208(12)
_cell_length_b                   26.557(2)
_cell_length_c                   8.6349(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3077.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2254
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    223.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408

_exptl_absorpt_coefficient_mu    2.537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
;

_diffrn_ambient_temperature      223.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Cu fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            8284
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_theta_min         4.68
_diffrn_reflns_theta_max         68.06
_diffrn_reflns_theta_full        68.06
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.952
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             2543
_reflns_number_gt                2274
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1643
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.034
_refine_ls_number_reflns         2543
_refine_ls_number_parameters     243
_refine_ls_number_restraints     334
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1016P)²+2.8370P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 895 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.43(3)

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'

_computing_data_collection       
;

Collect (Nonius B.V., 1998)
;
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.14698(12) 0.43658(6) 0.2388(2) 0.0681(5) Uani d U . D 1.0 . .
F F1 0.161(2) 0.4108(8) 0.0777(18) 0.084(4) Uani d U P D 0.52(6) A 1
F F2 0.0316(8) 0.4401(9) 0.206(3) 0.080(4) Uani d U P D 0.52(6) A 1
F F3 0.155(2) 0.4904(7) 0.167(3) 0.101(6) Uani d U P D 0.52(6) A 1
F F4 0.131(2) 0.4669(7) 0.3959(17) 0.088(4) Uani d U P D 0.52(6) A 1
F F5 0.2624(9) 0.4377(9) 0.266(4) 0.086(4) Uani d U P D 0.52(6) A 1
F F1A 0.129(2) 0.4104(9) 0.077(2) 0.082(4) Uani d U P D 0.48(6) A 2
F F2A 0.0345(11) 0.4490(9) 0.253(4) 0.085(5) Uani d U P D 0.48(6) A 2
F F3A 0.166(2) 0.4859(7) 0.145(3) 0.090(5) Uani d U P D 0.48(6) A 2
F F4A 0.169(2) 0.4661(8) 0.3921(18) 0.086(5) Uani d U P D 0.48(6) A 2
F F5A 0.2635(9) 0.4268(10) 0.220(3) 0.077(4) Uani d U P D 0.48(6) A 2
C C1 0.1348(4) 0.3790(2) 0.3414(7) 0.0554(13) Uani d U . . 1.0 . .
H H1 0.177 0.3732 0.4264 0.067 Uiso calc U . R 1.0 . .
C C2 0.0695(4) 0.3440(2) 0.3040(7) 0.0564(13) Uani d U . . 1.0 . .
H H2 0.027 0.3502 0.2197 0.068 Uiso calc U . R 1.0 . .
C C3 0.0587(5) 0.2949(2) 0.3870(8) 0.0561(13) Uani d U . . 1.0 . .
H H3A -0.0083 0.2921 0.4313 0.067 Uiso calc U . R 1.0 . .
H H3B 0.0686 0.2669 0.3147 0.067 Uiso calc U . R 1.0 . .
O O4 0.1320(3) 0.29291(14) 0.5078(5) 0.0542(9) Uani d U . . 1.0 . .
C C5 0.1303(4) 0.2515(2) 0.5987(8) 0.0530(12) Uani d U . . 1.0 . .
O O6 0.0741(3) 0.21683(16) 0.5765(5) 0.0679(11) Uani d U . . 1.0 . .
C C7 0.2040(5) 0.2567(2) 0.7275(9) 0.0634(14) Uani d U . . 1.0 . .
H H7A 0.2632 0.2742 0.6885 0.076 Uiso calc U . R 1.0 . .
H H7B 0.1748 0.2774 0.8096 0.076 Uiso calc U . R 1.0 . .
N N8 0.2339(4) 0.20907(19) 0.7922(7) 0.0625(12) Uani d U . . 1.0 . .
H H8 0.211(6) 0.202(3) 0.903(11) 0.09(2) Uiso d . . . 1.0 . .
C C9 0.3018(4) 0.1804(2) 0.7189(7) 0.0563(12) Uani d U . . 1.0 . .
O O10 0.3440(3) 0.19359(16) 0.6007(5) 0.0638(10) Uani d U . . 1.0 . .
O O11 0.3164(3) 0.13745(15) 0.7959(6) 0.0617(10) Uani d U . . 1.0 . .
C C12 0.3965(5) 0.1021(2) 0.7518(9) 0.0679(15) Uani d U . . 1.0 . .
C C13 0.3777(7) 0.0815(3) 0.5929(12) 0.093(2) Uani d U . . 1.0 . .
H H13A 0.3852 0.1082 0.5171 0.139 Uiso calc U . R 1.0 . .
H H13B 0.3105 0.0681 0.5877 0.139 Uiso calc U . R 1.0 . .
H H13C 0.4251 0.0549 0.571 0.139 Uiso calc U . R 1.0 . .
C C14 0.3841(7) 0.0621(3) 0.8773(12) 0.091(2) Uani d U . . 1.0 . .
H H14A 0.3175 0.0481 0.8719 0.136 Uiso calc U . R 1.0 . .
H H14B 0.3943 0.0773 0.9782 0.136 Uiso calc U . R 1.0 . .
H H14C 0.4327 0.0355 0.8617 0.136 Uiso calc U . R 1.0 . .
C C15 0.4961(5) 0.1283(3) 0.7672(10) 0.081(2) Uani d U . . 1.0 . .
H H15A 0.4991 0.1457 0.8658 0.122 Uiso calc U . R 1.0 . .
H H15B 0.5039 0.1524 0.6837 0.122 Uiso calc U . R 1.0 . .
H H15C 0.5492 0.1036 0.7619 0.122 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 F2A . 1.549(13) ?
S1 F3A . 1.561(13) ?
S1 F1 . 1.563(12) ?
S1 F3 . 1.563(13) ?
S1 F4A . 1.566(13) ?
S1 F5 . 1.568(11) ?
S1 F2 . 1.577(11) ?
S1 F1A . 1.582(13) ?
S1 F4 . 1.592(12) ?
S1 F5A . 1.594(12) ?
S1 C1 . 1.775(6) ?
C1 C2 . 1.319(8) ?
C1 H1 . 0.94 ?
C2 C3 . 1.494(8) ?
C2 H2 . 0.94 ?
C3 O4 . 1.435(7) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
O4 C5 . 1.352(7) ?
C5 O6 . 1.205(7) ?
C5 C7 . 1.494(9) ?
C7 N8 . 1.439(7) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
N8 C9 . 1.345(8) ?
N8 H8 . 1.02(9) ?
C9 O10 . 1.219(7) ?
C9 O11 . 1.334(7) ?
O11 C12 . 1.478(7) ?
C12 C13 . 1.498(12) ?
C12 C15 . 1.513(9) ?
C12 C14 . 1.527(10) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C13 H13C . 0.97 ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C14 H14C . 0.97 ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C15 H15C . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2A S1 F3A . . 91.2(12) ?
F1 S1 F3 . . 92.2(12) ?
F2A S1 F4A . . 90.5(9) ?
F3A S1 F4A . . 89.4(11) ?
F1 S1 F5 . . 91.1(8) ?
F3 S1 F5 . . 88.7(11) ?
F1 S1 F2 . . 89.3(8) ?
F3 S1 F2 . . 86.6(11) ?
F5 S1 F2 . . 175.3(10) ?
F2A S1 F1A . . 90.7(9) ?
F3A S1 F1A . . 86.2(12) ?
F4A S1 F1A . . 175.5(12) ?
F1 S1 F4 . . 175.5(11) ?
F3 S1 F4 . . 83.4(12) ?
F5 S1 F4 . . 89.8(8) ?
F2 S1 F4 . . 89.5(8) ?
F2A S1 F5A . . 176.7(12) ?
F3A S1 F5A . . 85.6(11) ?
F4A S1 F5A . . 89.2(8) ?
F1A S1 F5A . . 89.3(8) ?
F2A S1 C1 . . 93.2(9) ?
F3A S1 C1 . . 175.6(11) ?
F1 S1 C1 . . 94.5(9) ?
F3 S1 C1 . . 173.3(11) ?
F4A S1 C1 . . 91.5(8) ?
F5 S1 C1 . . 91.8(8) ?
F2 S1 C1 . . 92.9(8) ?
F1A S1 C1 . . 92.8(9) ?
F4 S1 C1 . . 89.9(8) ?
F5A S1 C1 . . 90.1(8) ?
C2 C1 S1 . . 123.1(5) ?
C2 C1 H1 . . 118.4 ?
S1 C1 H1 . . 118.4 ?
C1 C2 C3 . . 124.2(5) ?
C1 C2 H2 . . 117.9 ?
C3 C2 H2 . . 117.9 ?
O4 C3 C2 . . 108.3(5) ?
O4 C3 H3A . . 110.0 ?
C2 C3 H3A . . 110.0 ?
O4 C3 H3B . . 110.0 ?
C2 C3 H3B . . 110.0 ?
H3A C3 H3B . . 108.4 ?
C5 O4 C3 . . 116.1(4) ?
O6 C5 O4 . . 122.6(6) ?
O6 C5 C7 . . 127.1(5) ?
O4 C5 C7 . . 110.3(5) ?
N8 C7 C5 . . 113.1(5) ?
N8 C7 H7A . . 109.0 ?
C5 C7 H7A . . 109.0 ?
N8 C7 H7B . . 109.0 ?
C5 C7 H7B . . 109.0 ?
H7A C7 H7B . . 107.8 ?
C9 N8 C7 . . 120.2(6) ?
C9 N8 H8 . . 123.(5) ?
C7 N8 H8 . . 116.(5) ?
O10 C9 O11 . . 126.5(6) ?
O10 C9 N8 . . 123.1(5) ?
O11 C9 N8 . . 110.4(5) ?
C9 O11 C12 . . 121.4(5) ?
O11 C12 C13 . . 110.2(6) ?
O11 C12 C15 . . 109.1(6) ?
C13 C12 C15 . . 113.4(7) ?
O11 C12 C14 . . 100.3(5) ?
C13 C12 C14 . . 112.2(7) ?
C15 C12 C14 . . 110.7(6) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C12 C15 H15A . . 109.5 ?
C12 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C12 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F2A S1 C1 C2 . . . . 52.5(13) ?
F1 S1 C1 C2 . . . . -54.3(12) ?
F4A S1 C1 C2 . . . . 143.1(13) ?
F5 S1 C1 C2 . . . . -145.6(13) ?
F2 S1 C1 C2 . . . . 35.2(12) ?
F1A S1 C1 C2 . . . . -38.3(12) ?
F4 S1 C1 C2 . . . . 124.7(12) ?
F5A S1 C1 C2 . . . . -127.7(12) ?
S1 C1 C2 C3 . . . . 179.1(5) ?
C1 C2 C3 O4 . . . . -1.4(8) ?
C2 C3 O4 C5 . . . . 177.7(5) ?
C3 O4 C5 O6 . . . . 3.4(8) ?
C3 O4 C5 C7 . . . . -174.8(5) ?
O6 C5 C7 N8 . . . . 23.9(9) ?
O4 C5 C7 N8 . . . . -158.0(5) ?
C5 C7 N8 C9 . . . . 79.0(7) ?
C7 N8 C9 O10 . . . . 3.3(10) ?
C7 N8 C9 O11 . . . . -178.1(5) ?
O10 C9 O11 C12 . . . . 6.5(10) ?
N8 C9 O11 C12 . . . . -172.0(5) ?
C9 O11 C12 C13 . . . . -64.1(8) ?
C9 O11 C12 C15 . . . . 61.0(8) ?
C9 O11 C12 C14 . . . . 177.4(6) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 O6 6_554 0.94 2.56 3.191(7) 124.9 ?
C3 H3A O10 3_455 0.98 2.49 3.435(8) 161.3 ?
N8 H8 O10 8_545 1.02(9) 1.87(9) 2.892(7) 173.(7) ?

