# 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. 
# 
#######################################################################

data_x
_database_code_depnum_ccdc_archive 'CCDC 1554940'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 F I N O2 S'
_chemical_formula_weight         507.34

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   11.270(2)
_cell_length_b                   7.5710(15)
_cell_length_c                   13.366(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.99(3)
_cell_angle_gamma                90.00
_cell_volume                     1071.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    1.617
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.7381
_exptl_absorpt_correction_T_max  0.8550
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4145
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         25.40
_reflns_number_total             3936
_reflns_number_gt                3129
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0940P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_number_reflns         3936
_refine_ls_number_parameters     253
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1334
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.60963(5) 0.67212(10) -0.00605(4) 0.0538(2) Uani 1 1 d . . .
S S 0.5265(2) 0.4893(3) 0.27757(18) 0.0441(5) Uani 1 1 d . . .
F F 0.8093(5) 0.5012(8) 0.3099(4) 0.0565(14) Uani 1 1 d . . .
O1 O 0.4037(6) 0.5656(11) 0.2482(6) 0.068(2) Uani 1 1 d . . .
C1 C 0.5892(7) 0.4767(11) 0.4170(6) 0.0388(18) Uani 1 1 d . . .
C2 C 0.5327(11) 0.5734(15) 0.4785(9) 0.061(3) Uani 1 1 d . . .
H2A H 0.4600 0.6393 0.4462 0.073 Uiso 1 1 calc R . .
O2 O 0.5458(6) 0.3234(9) 0.2347(5) 0.0558(16) Uani 1 1 d . . .
N N 0.6153(6) 0.6306(9) 0.2410(5) 0.0362(19) Uani 1 1 d . . .
C3 C 0.5868(12) 0.5684(15) 0.5863(9) 0.068(3) Uani 1 1 d . . .
H3A H 0.5486 0.6316 0.6268 0.081 Uiso 1 1 calc R . .
C4 C 0.6961(9) 0.4737(12) 0.6395(8) 0.050(2) Uani 1 1 d . . .
C5 C 0.7458(9) 0.3789(14) 0.5755(7) 0.051(2) Uani 1 1 d . . .
H5A H 0.8179 0.3119 0.6078 0.062 Uiso 1 1 calc R . .
C6 C 0.6947(8) 0.3779(12) 0.4672(7) 0.046(2) Uani 1 1 d . . .
H6A H 0.7315 0.3104 0.4274 0.055 Uiso 1 1 calc R . .
C7 C 0.7553(14) 0.469(2) 0.7581(9) 0.090(4) Uani 1 1 d . . .
H7A H 0.8294 0.3964 0.7777 0.135 Uiso 1 1 calc R . .
H7B H 0.6962 0.4221 0.7885 0.135 Uiso 1 1 calc R . .
H7C H 0.7784 0.5872 0.7843 0.135 Uiso 1 1 calc R . .
C8 C 0.6017(9) 0.8247(13) 0.2583(7) 0.048(2) Uani 1 1 d . . .
H8A H 0.5434 0.8410 0.2967 0.058 Uiso 1 1 calc R . .
H8B H 0.5663 0.8828 0.1898 0.058 Uiso 1 1 calc R . .
C9 C 0.7264(9) 0.9097(12) 0.3200(9) 0.055(2) Uani 1 1 d . . .
C10 C 0.7897(12) 1.0037(17) 0.2657(12) 0.077(3) Uani 1 1 d . . .
H10A H 0.7553 1.0158 0.1921 0.092 Uiso 1 1 calc R . .
C11 C 0.9088(15) 1.083(2) 0.3234(19) 0.118(7) Uani 1 1 d U . .
H11A H 0.9531 1.1490 0.2894 0.142 Uiso 1 1 calc R . .
C12 C 0.9536(16) 1.056(2) 0.429(2) 0.130(8) Uani 1 1 d U . .
H12A H 1.0342 1.0984 0.4661 0.156 Uiso 1 1 calc R . .
C13 C 0.8914(16) 0.973(2) 0.4869(15) 0.117(7) Uani 1 1 d . . .
H13A H 0.9242 0.9691 0.5609 0.141 Uiso 1 1 calc R . .
C14 C 0.7735(12) 0.8926(16) 0.4288(11) 0.083(4) Uani 1 1 d . . .
H14A H 0.7291 0.8293 0.4641 0.100 Uiso 1 1 calc R . .
C15 C 0.7196(7) 0.5690(12) 0.2208(7) 0.0419(19) Uani 1 1 d . . .
C16 C 0.7449(7) 0.5708(11) 0.1317(7) 0.0372(18) Uani 1 1 d . . .
C17 C 0.8668(8) 0.5144(12) 0.1249(7) 0.045(2) Uani 1 1 d . . .
C18 C 0.8722(10) 0.3944(15) 0.0489(8) 0.061(3) Uani 1 1 d . . .
H18A H 0.7977 0.3542 -0.0014 0.073 Uiso 1 1 calc R . .
C19 C 0.9891(12) 0.3316(17) 0.0463(9) 0.076(3) Uani 1 1 d . . .
H19A H 0.9929 0.2473 -0.0032 0.092 Uiso 1 1 calc R . .
C20 C 1.0961(12) 0.399(2) 0.1189(11) 0.087(4) Uani 1 1 d . . .
H20A H 1.1741 0.3630 0.1167 0.105 Uiso 1 1 calc R . .
C21 C 1.0930(9) 0.5138(14) 0.1922(9) 0.061(3) Uani 1 1 d . . .
H21A H 1.1680 0.5550 0.2416 0.073 Uiso 1 1 calc R . .
C22 C 0.9785(9) 0.5730(15) 0.1959(8) 0.055(2) Uani 1 1 d . . .
H22A H 0.9775 0.6544 0.2477 0.066 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
I C16 2.093(9) . ?
S O1 1.425(7) . ?
S O2 1.428(7) . ?
S N 1.649(7) . ?
S C1 1.755(8) . ?
F C15 1.371(10) . ?
C1 C6 1.371(12) . ?
C1 C2 1.405(13) . ?
C2 C3 1.360(16) . ?
C2 H2A 0.9300 . ?
N C15 1.374(10) . ?
N C8 1.504(13) . ?
C3 C4 1.392(15) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(13) . ?
C4 C7 1.495(15) . ?
C5 C6 1.364(13) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.509(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.372(16) . ?
C9 C10 1.377(16) . ?
C10 C11 1.43(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.34(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.36(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.427(19) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.317(11) . ?
C16 C17 1.470(11) . ?
C17 C22 1.365(13) . ?
C17 C18 1.380(13) . ?
C18 C19 1.412(15) . ?
C18 H18A 0.9300 . ?
C19 C20 1.363(17) . ?
C19 H19A 0.9300 . ?
C20 C21 1.319(17) . ?
C20 H20A 0.9300 . ?
C21 C22 1.383(13) . ?
C21 H21A 0.9300 . ?
C22 H22A 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
O1 S O2 120.9(5) . . ?
O1 S N 106.6(4) . . ?
O2 S N 105.1(4) . . ?
O1 S C1 108.3(4) . . ?
O2 S C1 108.5(4) . . ?
N S C1 106.6(4) . . ?
C6 C1 C2 119.2(9) . . ?
C6 C1 S 121.1(7) . . ?
C2 C1 S 119.6(7) . . ?
C3 C2 C1 118.5(10) . . ?
C3 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C15 N C8 120.1(7) . . ?
C15 N S 119.0(6) . . ?
C8 N S 119.0(6) . . ?
C2 C3 C4 123.6(9) . . ?
C2 C3 H3A 118.2 . . ?
C4 C3 H3A 118.2 . . ?
C5 C4 C3 115.4(9) . . ?
C5 C4 C7 121.3(10) . . ?
C3 C4 C7 123.3(10) . . ?
C6 C5 C4 123.4(9) . . ?
C6 C5 H5A 118.3 . . ?
C4 C5 H5A 118.3 . . ?
C5 C6 C1 119.8(9) . . ?
C5 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N C8 C9 112.1(7) . . ?
N C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 121.7(11) . . ?
C14 C9 C8 119.3(10) . . ?
C10 C9 C8 119.0(10) . . ?
C9 C10 C11 119.4(15) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
C12 C11 C10 116.8(18) . . ?
C12 C11 H11A 121.6 . . ?
C10 C11 H11A 121.6 . . ?
C11 C12 C13 125.8(18) . . ?
C11 C12 H12A 117.1 . . ?
C13 C12 H12A 117.1 . . ?
C12 C13 C14 116.9(18) . . ?
C12 C13 H13A 121.6 . . ?
C14 C13 H13A 121.6 . . ?
C9 C14 C13 119.2(16) . . ?
C9 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C16 C15 F 117.8(7) . . ?
C16 C15 N 129.7(8) . . ?
F C15 N 112.5(7) . . ?
C15 C16 C17 123.2(8) . . ?
C15 C16 I 118.8(6) . . ?
C17 C16 I 117.9(6) . . ?
C22 C17 C18 117.6(9) . . ?
C22 C17 C16 121.5(8) . . ?
C18 C17 C16 120.9(8) . . ?
C17 C18 C19 121.1(10) . . ?
C17 C18 H18A 119.5 . . ?
C19 C18 H18A 119.5 . . ?
C20 C19 C18 117.5(10) . . ?
C20 C19 H19A 121.2 . . ?
C18 C19 H19A 121.2 . . ?
C21 C20 C19 122.3(10) . . ?
C21 C20 H20A 118.9 . . ?
C19 C20 H20A 118.9 . . ?
C20 C21 C22 120.1(11) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C17 C22 C21 121.4(10) . . ?
C17 C22 H22A 119.3 . . ?
C21 C22 H22A 119.3 . . ?

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
O1 S C1 C6 166.9(7) . . . . ?
O2 S C1 C6 34.1(8) . . . . ?
N S C1 C6 -78.6(8) . . . . ?
O1 S C1 C2 -15.0(9) . . . . ?
O2 S C1 C2 -147.9(8) . . . . ?
N S C1 C2 99.4(8) . . . . ?
C6 C1 C2 C3 1.4(15) . . . . ?
S C1 C2 C3 -176.7(9) . . . . ?
O1 S N C15 -155.1(6) . . . . ?
O2 S N C15 -25.6(7) . . . . ?
C1 S N C15 89.4(7) . . . . ?
O1 S N C8 41.0(7) . . . . ?
O2 S N C8 170.4(6) . . . . ?
C1 S N C8 -74.6(7) . . . . ?
C1 C2 C3 C4 0.6(18) . . . . ?
C2 C3 C4 C5 -1.9(16) . . . . ?
C2 C3 C4 C7 179.7(12) . . . . ?
C3 C4 C5 C6 1.2(14) . . . . ?
C7 C4 C5 C6 179.6(10) . . . . ?
C4 C5 C6 C1 0.7(14) . . . . ?
C2 C1 C6 C5 -2.0(13) . . . . ?
S C1 C6 C5 176.1(7) . . . . ?
C15 N C8 C9 -37.6(11) . . . . ?
S N C8 C9 126.2(7) . . . . ?
N C8 C9 C14 -80.3(11) . . . . ?
N C8 C9 C10 100.2(11) . . . . ?
C14 C9 C10 C11 1.4(18) . . . . ?
C8 C9 C10 C11 -179.2(10) . . . . ?
C9 C10 C11 C12 1(2) . . . . ?
C10 C11 C12 C13 -5(3) . . . . ?
C11 C12 C13 C14 6(3) . . . . ?
C10 C9 C14 C13 -0.5(17) . . . . ?
C8 C9 C14 C13 -179.9(10) . . . . ?
C12 C13 C14 C9 -3(2) . . . . ?
C8 N C15 C16 -79.1(12) . . . . ?
S N C15 C16 117.1(10) . . . . ?
C8 N C15 F 98.9(9) . . . . ?
S N C15 F -64.8(8) . . . . ?
F C15 C16 C17 -4.0(13) . . . . ?
N C15 C16 C17 174.0(8) . . . . ?
F C15 C16 I 179.7(6) . . . . ?
N C15 C16 I -2.4(13) . . . . ?
C15 C16 C17 C22 -47.9(13) . . . . ?
I C16 C17 C22 128.4(8) . . . . ?
C15 C16 C17 C18 129.4(10) . . . . ?
I C16 C17 C18 -54.2(11) . . . . ?
C22 C17 C18 C19 1.4(16) . . . . ?
C16 C17 C18 C19 -176.1(10) . . . . ?
C17 C18 C19 C20 -2.5(19) . . . . ?
C18 C19 C20 C21 3(2) . . . . ?
C19 C20 C21 C22 -2(2) . . . . ?
C18 C17 C22 C21 -0.3(15) . . . . ?
C16 C17 C22 C21 177.1(9) . . . . ?
C20 C21 C22 C17 0.4(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.092
