# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1860794'
_audit_update_record             
;
2018-08-07 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(E)-phenyl(4,4,4-trifluoro-2-iodo-3-(iodomethyl)-1-phenylbut-1-en-1-yl)sulfane
_chemical_name_common            ?
_chemical_melting_point          334K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 F3 I2 S'
_chemical_formula_weight         574.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6631(5)
_cell_length_b                   9.5398(5)
_cell_length_c                   13.2336(7)
_cell_angle_alpha                99.341(2)
_cell_angle_beta                 97.979(2)
_cell_angle_gamma                111.362(2)
_cell_volume                     981.45(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6832
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    3.334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3216
_exptl_absorpt_correction_T_max  0.4246
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11443
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3430
_reflns_number_gt                3119
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)²+5.9759P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3430
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.7805(3) 0.29950(19) -0.37173(13) 0.0512(4) Uani 1 1 d . . .
F1 F 1.0594(8) 0.3075(10) -0.0959(5) 0.124(3) Uani 1 1 d . . .
F2 F 1.0979(8) 0.1113(10) -0.1377(6) 0.117(2) Uani 1 1 d . . .
F3 F 0.9523(11) 0.1299(10) -0.0362(5) 0.125(3) Uani 1 1 d . . .
I1 I 0.56889(7) 0.12969(6) -0.08951(4) 0.0615(2) Uani 1 1 d . . .
I2 I 0.56687(8) -0.14888(6) -0.38585(5) 0.0721(2) Uani 1 1 d . . .
C1 C 0.4631(9) 0.3772(8) -0.2980(5) 0.0492(16) Uani 1 1 d . . .
H1A H 0.4237 0.3071 -0.3627 0.059 Uiso 1 1 calc R . .
C2 C 0.3789(11) 0.4681(10) -0.2693(6) 0.063(2) Uani 1 1 d . . .
H2A H 0.2830 0.4598 -0.3154 0.076 Uiso 1 1 calc R . .
C3 C 0.4329(11) 0.5723(10) -0.1731(6) 0.061(2) Uani 1 1 d . . .
H3A H 0.3723 0.6315 -0.1540 0.074 Uiso 1 1 calc R . .
C4 C 0.5755(11) 0.5873(9) -0.1069(6) 0.061(2) Uani 1 1 d . . .
H4A H 0.6135 0.6583 -0.0426 0.073 Uiso 1 1 calc R . .
C5 C 0.6647(9) 0.4979(8) -0.1343(6) 0.0519(17) Uani 1 1 d . . .
H5A H 0.7627 0.5103 -0.0884 0.062 Uiso 1 1 calc R . .
C6 C 0.6095(8) 0.3896(7) -0.2298(5) 0.0393(13) Uani 1 1 d . . .
C7 C 0.7012(8) 0.2900(7) -0.2550(5) 0.0404(14) Uani 1 1 d . . .
C8 C 0.8826(8) 0.5016(8) -0.3632(5) 0.0437(14) Uani 1 1 d . . .
C9 C 0.8426(11) 0.5556(9) -0.4491(6) 0.0600(19) Uani 1 1 d . . .
H9A H 0.7550 0.4904 -0.5053 0.072 Uiso 1 1 calc R . .
C10 C 0.9333(11) 0.7073(8) -0.4514(6) 0.0585(19) Uani 1 1 d . . .
H10A H 0.9083 0.7426 -0.5106 0.070 Uiso 1 1 calc R . .
C11 C 1.0597(9) 0.8074(8) -0.3680(6) 0.0509(17) Uani 1 1 d . . .
C12 C 1.0935(10) 0.7517(9) -0.2824(7) 0.0607(19) Uani 1 1 d . . .
H12A H 1.1775 0.8178 -0.2247 0.073 Uiso 1 1 calc R . .
C13 C 1.0058(9) 0.5993(8) -0.2794(6) 0.0531(17) Uani 1 1 d . . .
H13A H 1.0310 0.5639 -0.2204 0.064 Uiso 1 1 calc R . .
C14 C 1.1589(12) 0.9744(9) -0.3718(8) 0.071(2) Uani 1 1 d . . .
H14A H 1.2408 1.0273 -0.3071 0.106 Uiso 1 1 calc R . .
H14B H 1.0821 1.0249 -0.3817 0.106 Uiso 1 1 calc R . .
H14C H 1.2162 0.9761 -0.4290 0.106 Uiso 1 1 calc R . .
C15 C 0.7199(9) 0.1891(8) -0.2011(5) 0.0455(15) Uani 1 1 d . . .
C16 C 0.8373(9) 0.1046(8) -0.2143(6) 0.0519(16) Uani 1 1 d . . .
H16A H 0.8846 0.1312 -0.2751 0.062 Uiso 1 1 calc R . .
C17 C 1.0143(12) 0.1713(9) -0.1069(7) 0.058(2) Uani 1 1 d . . .
C18 C 0.7509(12) -0.0698(10) -0.2402(7) 0.064(2) Uani 1 1 d . . .
H18A H 0.6951 -0.1031 -0.1845 0.077 Uiso 1 1 calc R . .
H18B H 0.8347 -0.1142 -0.2458 0.077 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.778(6) . ?
S1 C8 1.781(7) . ?
F1 C17 1.190(10) . ?
F2 C17 1.151(10) . ?
F3 C17 1.194(11) . ?
I1 C15 2.116(6) . ?
I2 C18 2.151(9) . ?
C1 C2 1.364(11) . ?
C1 C6 1.406(9) . ?
C1 H1A 0.9300 . ?
C2 C3 1.382(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.358(11) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(10) . ?
C4 H4A 0.9300 . ?
C5 C6 1.393(9) . ?
C5 H5A 0.9300 . ?
C6 C7 1.471(9) . ?
C7 C15 1.329(9) . ?
C8 C13 1.360(10) . ?
C8 C9 1.374(10) . ?
C9 C10 1.381(10) . ?
C9 H9A 0.9300 . ?
C10 C11 1.375(11) . ?
C10 H10A 0.9300 . ?
C11 C12 1.367(11) . ?
C11 C14 1.523(10) . ?
C12 C13 1.383(10) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.522(10) . ?
C16 C18 1.511(11) . ?
C16 C17 1.780(12) . ?
C16 H16A 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 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
C7 S1 C8 103.8(3) . . ?
C2 C1 C6 120.0(6) . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C1 C2 C3 121.5(7) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 119.2(7) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 120.6(7) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 120.8(7) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C1 117.8(6) . . ?
C5 C6 C7 120.0(6) . . ?
C1 C6 C7 122.2(6) . . ?
C15 C7 C6 125.1(6) . . ?
C15 C7 S1 118.5(5) . . ?
C6 C7 S1 116.2(4) . . ?
C13 C8 C9 119.9(6) . . ?
C13 C8 S1 122.4(5) . . ?
C9 C8 S1 117.4(5) . . ?
C8 C9 C10 119.6(7) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C11 C10 C9 121.3(7) . . ?
C11 C10 H10A 119.3 . . ?
C9 C10 H10A 119.3 . . ?
C12 C11 C10 117.8(7) . . ?
C12 C11 C14 121.4(7) . . ?
C10 C11 C14 120.7(7) . . ?
C11 C12 C13 121.6(7) . . ?
C11 C12 H12A 119.2 . . ?
C13 C12 H12A 119.2 . . ?
C8 C13 C12 119.7(7) . . ?
C8 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 C16 126.0(6) . . ?
C7 C15 I1 118.8(5) . . ?
C16 C15 I1 115.2(4) . . ?
C18 C16 C15 115.0(6) . . ?
C18 C16 C17 110.7(6) . . ?
C15 C16 C17 112.9(5) . . ?
C18 C16 H16A 105.8 . . ?
C15 C16 H16A 105.8 . . ?
C17 C16 H16A 105.8 . . ?
F2 C17 F1 119.5(10) . . ?
F2 C17 F3 116.6(9) . . ?
F1 C17 F3 110.8(8) . . ?
F2 C17 C16 102.3(7) . . ?
F1 C17 C16 100.7(7) . . ?
F3 C17 C16 103.6(7) . . ?
C16 C18 I2 109.8(5) . . ?
C16 C18 H18A 109.7 . . ?
I2 C18 H18A 109.7 . . ?
C16 C18 H18B 109.7 . . ?
I2 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.431
_refine_diff_density_min         -1.335
_refine_diff_density_rms         0.121
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hexane'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_exp_479
_database_code_depnum_ccdc_archive 'CCDC 1867549'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_audit_creation_date             2018-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 F3 N O2 S'
_chemical_formula_sum            'C17 H12 F3 N O2 S'
_chemical_formula_weight         351.34
_chemical_melting_point          326
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'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.09320(10)
_cell_length_b                   16.40420(10)
_cell_length_c                   15.81510(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.3940(10)
_cell_angle_gamma                90
_cell_volume                     1554.84(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24614
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2880
_cell_measurement_theta_min      3.9140
_shelx_estimated_absorpt_T_max   0.636
_shelx_estimated_absorpt_T_min   0.410
_exptl_absorpt_coefficient_mu    2.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1193
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            37602
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.397
_diffrn_reflns_theta_min         3.916
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  64.00   1.00    1.00    --    0.00  82.00 120.00   95
  2  ω    -19.00  89.00   1.00    1.00    --    0.00  38.00-180.00  108
  3  ω      9.00  80.00   1.00    1.00    --    0.00  82.00  60.00   71
  4  ω    -32.00  65.00   1.00    1.00    --    0.00  82.00 -30.00   97
  5  ω    -23.00  15.00   1.00    1.00    --    0.00  19.00 -30.00   38
  6  ω    -27.00   2.00   1.00    1.00    --    0.00  82.00  60.00   29
  7  ω     26.00  85.00   1.00    1.00    --    0.00  38.00-120.00   59
  8  ω    -17.00  23.00   1.00    1.00    --    0.00  38.00-120.00   40
  9  ω    -19.00  69.00   1.00    1.00    --    0.00  38.00  60.00   88
 10  ω     30.00  80.00   1.00    1.00    --    0.00  19.00 -30.00   50
 11  ω    113.00 184.00   1.00    1.00    --   95.80  81.00 -99.20   71
 12  ω    121.00 146.00   1.00    1.00    --   95.80  71.00  -4.32   25
 13  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  38.90   25
 14  ω     66.00 179.00   1.00    1.00    --   95.80  76.00 137.93  113
 15  ω     67.00  94.00   1.00    1.00    --   95.80  71.00  -4.32   27
 16  ω     63.00 108.00   1.00    1.00    --   95.80  81.00 -99.20   45
 17  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  24.28   26
 18  ω    130.00 162.00   1.00    1.00    --   95.80  73.00  84.23   32
 19  ω    103.00 185.00   1.00    1.00    --   95.80  61.00-180.00   82
 20  ω     71.00  97.00   1.00    1.00    --   95.80  61.00-180.00   26
 21  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 22  ω     41.00  76.00   1.00    1.00    --   95.80 -82.00-150.00   35
 23  ω     82.00 125.00   1.00    1.00    --   95.80 -82.00-150.00   43
 24  ω     64.00  90.00   1.00    1.00    --   95.80  82.00 -90.00   26
 25  ω     65.00 103.00   1.00    1.00    --   95.80  77.00   0.00   38
 26  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 27  ω     63.00 185.00   1.00    1.00    --   95.80  82.00   0.00  122
 28  ω     66.00  91.00   1.00    1.00    --   95.80  82.00 150.00   25
 29  ω     71.00  97.00   1.00    1.00    --   95.80  61.00 -60.00   26
 30  ω     65.00  92.00   1.00    1.00    --   95.80  77.00 120.00   27
 31  ω     67.00 104.00   1.00    1.00    --   95.80  73.00  84.23   37
 32  ω     73.00 118.00   1.00    1.00    --   95.80  52.00 -97.03   45
 33  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 34  ω    113.00 185.00   1.00    1.00    --   95.80  82.00-120.00   72
 35  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 36  ω     61.00 120.00   1.00    1.00    --   95.80 -82.00  90.00   59
 37  ω    137.00 167.00   1.00    1.00    --   95.80  48.00-121.52   30
 38  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 39  ω     66.00 100.00   1.00    1.00    --   95.80  77.00 -30.00   34
 40  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 41  ω      7.00 126.00   1.00    1.00    --   95.80 -82.00   0.00  119
 42  ω     65.00 137.00   1.00    1.00    --   95.80  77.00  90.00   72
 43  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 44  ω    102.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   83
 45  ω     75.00 124.00   1.00    1.00    --   95.80  45.00 150.00   49
 46  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 47  ω     75.00 118.00   1.00    1.00    --   95.80  45.00-150.00   43
 48  ω    123.00 149.00   1.00    1.00    --   95.80  45.00-150.00   26
 49  ω     65.00  96.00   1.00    1.00    --   95.80  77.00-150.00   31
 50  ω     65.00 113.00   1.00    1.00    --   95.80  77.00 150.00   48
 51  ω    100.00 126.00   1.00    1.00    --   95.80 -82.00 -60.00   26
 52  ω     77.00 181.00   1.00    1.00    --   95.80  45.00 -30.00  104
 53  ω     80.00 185.00   1.00    1.00    --   95.80  45.00  90.00  105
 54  ω     71.00 170.00   1.00    1.00    --   95.80  61.00  30.00   99
 55  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 56  ω     43.00 125.00   1.00    1.00    --   95.80 -82.00 150.00   82
 57  ω     16.00  68.00   1.00    1.00    --   95.80 -82.00 -60.00   52
 58  ω     74.00  99.00   1.00    1.00    --   95.80  48.00-121.52   25
 59  ω     16.00 123.00   1.00    1.00    --   95.80 -82.00 -90.00  107
 60  ω     72.00  98.00   1.00    1.00    --   95.80  61.00-150.00   26
 61  ω    116.00 180.00   1.00    1.00    --   95.80  61.00-150.00   64
 62  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 63  ω    147.00 172.00   1.00    1.00    --   95.80  77.00  24.28   25
 64  ω    152.00 184.00   1.00    1.00    --   95.80  79.00 -44.03   32
 65  ω     64.00  95.00   1.00    1.00    --   95.80  79.00 -44.03   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0331482000
_diffrn_orient_matrix_UB_12      -0.0708469000
_diffrn_orient_matrix_UB_13      0.0603400000
_diffrn_orient_matrix_UB_21      0.0464419000
_diffrn_orient_matrix_UB_22      0.0582353000
_diffrn_orient_matrix_UB_23      0.0776035000
_diffrn_orient_matrix_UB_31      -0.2507157000
_diffrn_orient_matrix_UB_32      0.0201630000
_diffrn_orient_matrix_UB_33      -0.0119619000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3026
_reflns_number_total             3160
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+0.5834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1049
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.b X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.14743(6) 0.31320(2) 0.48224(2) 0.02017(14) Uani 1 1 d . . . . .
F1 F 1.22342(16) 0.20145(7) 0.65091(6) 0.0371(3) Uani 1 1 d . . . . .
F2 F 1.21190(18) 0.11842(6) 0.54526(7) 0.0378(3) Uani 1 1 d . . . . .
F3 F 1.02301(17) 0.09308(7) 0.64510(7) 0.0387(3) Uani 1 1 d . . . . .
O1 O 0.9428(2) 0.61111(7) 0.74291(7) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.60485(19) 0.58374(7) 0.67987(7) 0.0284(3) Uani 1 1 d . . . . .
N1 N 0.8067(2) 0.57124(8) 0.69264(8) 0.0227(3) Uani 1 1 d . . . . .
C1 C 0.6048(3) 0.09686(9) 0.39465(9) 0.0255(3) Uani 1 1 d . . . . .
H1 H 0.730194 0.075242 0.429753 0.031 Uiso 1 1 calc R . . . .
C2 C 0.4133(3) 0.04975(10) 0.37289(10) 0.0291(4) Uani 1 1 d . . . . .
H2 H 0.410892 -0.003145 0.393866 0.035 Uiso 1 1 calc R . . . .
C3 C 0.2255(3) 0.08118(10) 0.32003(10) 0.0305(4) Uani 1 1 d . . . . .
H3 H 0.096211 0.050056 0.307090 0.037 Uiso 1 1 calc R . . . .
C4 C 0.2315(3) 0.15924(11) 0.28655(10) 0.0300(4) Uani 1 1 d . . . . .
H4 H 0.107375 0.179999 0.249962 0.036 Uiso 1 1 calc R . . . .
C5 C 0.4230(3) 0.20628(10) 0.30775(9) 0.0252(3) Uani 1 1 d . . . . .
H5 H 0.427249 0.258115 0.284296 0.030 Uiso 1 1 calc R . . . .
C6 C 0.6094(3) 0.17651(9) 0.36400(9) 0.0219(3) Uani 1 1 d . . . . .
C7 C 0.7986(2) 0.23257(9) 0.38912(9) 0.0212(3) Uani 1 1 d . . . . .
H7 H 0.834615 0.265797 0.345965 0.025 Uiso 1 1 calc R . . . .
C8 C 0.9251(2) 0.24103(8) 0.46757(9) 0.0187(3) Uani 1 1 d . . . . .
C9 C 0.8904(2) 0.19857(8) 0.54723(9) 0.0190(3) Uani 1 1 d . . . . .
C10 C 0.7035(3) 0.20358(9) 0.57866(9) 0.0230(3) Uani 1 1 d . . . . .
H10A H 0.585171 0.234906 0.550618 0.028 Uiso 1 1 calc R . . . .
H10B H 0.690520 0.175760 0.628767 0.028 Uiso 1 1 calc R . . . .
C11 C 1.0867(3) 0.15273(10) 0.59664(10) 0.0256(3) Uani 1 1 d . . . . .
C12 C 0.8910(2) 0.50541(9) 0.64478(9) 0.0196(3) Uani 1 1 d . . . . .
C13 C 1.1118(2) 0.48209(10) 0.66546(9) 0.0229(3) Uani 1 1 d . . . . .
H13 H 1.208231 0.507140 0.710197 0.027 Uiso 1 1 calc R . . . .
C14 C 1.1860(2) 0.42032(9) 0.61780(9) 0.0222(3) Uani 1 1 d . . . . .
H14 H 1.332810 0.402317 0.631745 0.027 Uiso 1 1 calc R . . . .
C15 C 1.0411(2) 0.38492(8) 0.54879(9) 0.0186(3) Uani 1 1 d . . . . .
C16 C 0.8183(2) 0.40931(9) 0.53000(9) 0.0209(3) Uani 1 1 d . . . . .
H16 H 0.721303 0.385225 0.484753 0.025 Uiso 1 1 calc R . . . .
C17 C 0.7422(2) 0.46919(9) 0.57864(9) 0.0204(3) Uani 1 1 d . . . . .
H17 H 0.593262 0.485094 0.567298 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.7827(15) . ?
S1 C15 1.7768(14) . ?
F1 C11 1.3460(19) . ?
F2 C11 1.3353(18) . ?
F3 C11 1.3427(17) . ?
O1 N1 1.2287(17) . ?
O2 N1 1.2274(17) . ?
N1 C12 1.4639(19) . ?
C1 H1 0.9300 . ?
C1 C2 1.390(2) . ?
C1 C6 1.396(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(2) . ?
C6 C7 1.472(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.344(2) . ?
C8 C9 1.4875(18) . ?
C9 C10 1.325(2) . ?
C9 C11 1.506(2) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C12 C13 1.380(2) . ?
C12 C17 1.3883(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.400(2) . ?
C15 C16 1.395(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(2) . ?
C17 H17 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
C15 S1 C8 99.62(6) . . ?
O1 N1 C12 117.94(13) . . ?
O2 N1 O1 123.84(13) . . ?
O2 N1 C12 118.22(12) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.21(15) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.41(15) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.76(15) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.95(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.69(15) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.86(15) . . ?
C1 C6 C7 123.72(14) . . ?
C5 C6 C7 117.41(13) . . ?
C6 C7 H7 116.4 . . ?
C8 C7 C6 127.16(13) . . ?
C8 C7 H7 116.4 . . ?
C7 C8 S1 118.96(11) . . ?
C7 C8 C9 126.02(13) . . ?
C9 C8 S1 114.92(10) . . ?
C8 C9 C11 116.90(12) . . ?
C10 C9 C8 123.48(13) . . ?
C10 C9 C11 119.48(13) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
F1 C11 C9 112.12(13) . . ?
F2 C11 F1 106.41(13) . . ?
F2 C11 F3 107.20(13) . . ?
F2 C11 C9 112.46(12) . . ?
F3 C11 F1 106.15(12) . . ?
F3 C11 C9 112.08(12) . . ?
C13 C12 N1 119.99(13) . . ?
C13 C12 C17 122.43(14) . . ?
C17 C12 N1 117.58(13) . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.26(13) . . ?
C14 C13 H13 120.9 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.35(14) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 S1 119.37(11) . . ?
C16 C15 S1 120.57(11) . . ?
C16 C15 C14 119.97(13) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.87(13) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 120.5 . . ?
C16 C17 C12 119.05(14) . . ?
C16 C17 H17 120.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.253
_oxdiff_exptl_absorpt_empirical_full_min 0.266
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/DCM'
