# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_jk181120_2
_database_code_depnum_ccdc_archive 'CCDC 1947034'
loop_
_audit_author_name
_audit_author_address
'Ewa Pietrasiak'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2019-10-07 downloaded from the CCDC.
;
_audit_creation_date             2018-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H4 Cl F3 I N O S'
_chemical_formula_sum            'C7 H4 Cl F3 I N O S'
_chemical_formula_weight         369.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.1427(6)
_cell_length_b                   7.2141(9)
_cell_length_c                   27.595(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1023.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5757
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   0.840
_shelx_estimated_absorpt_T_min   0.563
_exptl_absorpt_coefficient_mu    3.606
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1172 before and 0.0583 after correction. The Ratio of minimum to maximum transmission is 0.7463. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'MeCN evaporation at rt'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14295
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         2.918
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART Apex2'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2136
_reflns_number_total             2177
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.609
_refine_diff_density_min         -1.492
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details 
;
 Flack x determined using 823 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.201
_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)+(0.0127P)²+5.4240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0692
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
I1 I 0.33591(10) 0.43369(7) 0.56082(2) 0.01648(13) Uani 1 1 d . . . . .
Cl1 Cl 0.6873(4) 0.4668(3) 0.49488(7) 0.0223(4) Uani 1 1 d . . . . .
S1 S 0.0972(4) 0.5761(4) 0.65494(7) 0.0204(4) Uani 1 1 d . . . . .
F3 F 0.3109(12) 0.6011(7) 0.74195(17) 0.0366(14) Uani 1 1 d . . . . .
F1 F 0.4772(11) 0.3925(7) 0.69717(19) 0.0311(13) Uani 1 1 d . . . . .
O1 O -0.1227(12) 0.6655(10) 0.6767(2) 0.0296(15) Uani 1 1 d . . . . .
F2 F 0.0989(13) 0.3501(10) 0.7276(2) 0.055(2) Uani 1 1 d . . . . .
N1 N 0.0625(13) 0.4282(12) 0.6174(2) 0.0234(15) Uani 1 1 d . . . . .
C7 C 0.2571(17) 0.4734(12) 0.7089(3) 0.023(2) Uani 1 1 d . . . . .
C2 C 0.3301(18) 0.7340(10) 0.6336(3) 0.0171(15) Uani 1 1 d . . . . .
C6 C 0.6430(18) 0.8011(11) 0.5720(3) 0.0206(17) Uani 1 1 d . . . . .
H6 H 0.7319 0.7690 0.5430 0.025 Uiso 1 1 calc R . . . .
C3 C 0.3794(17) 0.9009(11) 0.6569(3) 0.0225(19) Uani 1 1 d . . . . .
H3 H 0.2860 0.9354 0.6852 0.027 Uiso 1 1 calc R . . . .
C5 C 0.6964(19) 0.9664(11) 0.5960(3) 0.0240(19) Uani 1 1 d . . . . .
H5 H 0.8249 1.0475 0.5833 0.029 Uiso 1 1 calc R . . . .
C1 C 0.4588(16) 0.6868(11) 0.5913(3) 0.0159(16) Uani 1 1 d . . . . .
C4 C 0.5682(19) 1.0148(12) 0.6377(3) 0.027(2) Uani 1 1 d . . . . .
H4 H 0.6098 1.1280 0.6535 0.033 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0169(2) 0.0173(2) 0.0152(2) -0.0018(2) -0.0010(2) -0.0016(2)
Cl1 0.0188(10) 0.0246(10) 0.0235(9) -0.0050(8) 0.0038(8) -0.0003(9)
S1 0.0162(10) 0.0283(10) 0.0166(9) 0.0003(9) 0.0001(7) 0.0002(9)
F3 0.050(3) 0.039(3) 0.021(3) -0.008(2) -0.011(3) 0.020(3)
F1 0.035(3) 0.027(3) 0.032(3) -0.001(2) -0.003(2) 0.012(2)
O1 0.018(3) 0.050(4) 0.020(3) 0.000(3) 0.003(3) 0.005(3)
F2 0.051(4) 0.075(5) 0.038(3) 0.030(3) -0.006(3) -0.030(4)
N1 0.021(3) 0.036(4) 0.013(3) -0.002(4) 0.002(3) -0.007(4)
C7 0.025(5) 0.021(5) 0.021(4) -0.003(3) -0.002(3) 0.001(3)
C2 0.018(4) 0.018(4) 0.016(4) 0.004(3) 0.003(4) 0.001(4)
C6 0.024(4) 0.021(4) 0.017(4) 0.002(3) 0.000(4) 0.006(4)
C3 0.024(5) 0.021(4) 0.022(4) -0.002(3) -0.002(3) 0.006(4)
C5 0.027(5) 0.016(4) 0.029(4) 0.004(3) 0.000(4) -0.006(4)
C1 0.015(4) 0.014(4) 0.019(4) -0.003(3) -0.002(3) 0.001(3)
C4 0.037(5) 0.017(4) 0.028(5) -0.005(3) -0.004(4) 0.003(4)

_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
I1 Cl1 2.576(2) . ?
I1 N1 2.103(6) . ?
I1 C1 2.108(8) . ?
S1 O1 1.433(6) . ?
S1 N1 1.497(8) . ?
S1 C7 1.856(9) . ?
S1 C2 1.755(8) . ?
F3 C7 1.326(10) . ?
F1 C7 1.314(10) . ?
F2 C7 1.311(10) . ?
C2 C3 1.389(11) . ?
C2 C1 1.383(11) . ?
C6 H6 0.9500 . ?
C6 C5 1.392(11) . ?
C6 C1 1.365(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(13) . ?
C5 H5 0.9500 . ?
C5 C4 1.370(12) . ?
C4 H4 0.9500 . ?

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
N1 I1 Cl1 174.9(2) . . ?
N1 I1 C1 85.4(3) . . ?
C1 I1 Cl1 89.5(2) . . ?
O1 S1 N1 121.1(4) . . ?
O1 S1 C7 101.1(4) . . ?
O1 S1 C2 112.8(4) . . ?
N1 S1 C7 108.8(4) . . ?
N1 S1 C2 108.1(4) . . ?
C2 S1 C7 103.1(4) . . ?
S1 N1 I1 114.9(4) . . ?
F3 C7 S1 111.5(6) . . ?
F1 C7 S1 111.2(6) . . ?
F1 C7 F3 107.4(7) . . ?
F2 C7 S1 108.2(6) . . ?
F2 C7 F3 109.3(7) . . ?
F2 C7 F1 109.3(7) . . ?
C3 C2 S1 122.1(6) . . ?
C1 C2 S1 116.8(6) . . ?
C1 C2 C3 121.1(8) . . ?
C5 C6 H6 121.1 . . ?
C1 C6 H6 121.1 . . ?
C1 C6 C5 117.9(8) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 C2 117.9(8) . . ?
C4 C3 H3 121.1 . . ?
C6 C5 H5 119.2 . . ?
C4 C5 C6 121.6(8) . . ?
C4 C5 H5 119.2 . . ?
C2 C1 I1 114.0(6) . . ?
C6 C1 I1 125.1(6) . . ?
C6 C1 C2 120.9(8) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(8) . . ?
C5 C4 H4 119.7 . . ?

_shelx_res_file                  
;
    jk181120_2.res created by SHELXL-2014/7

TITL jk181120_2_a.res in P2(1)2(1)2(1)
REM Old TITL jk181120_2 in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.063, Rweak 0.049, Alpha 0.019, Orientation as input
REM Flack x = 0.002 ( 0.013 ) from Parsons' quotients
REM Formula found by SHELXT: C8 O4 S2 I
CELL 0.71073 5.1427 7.2141 27.5954 90 90 90
ZERR 4 0.0006 0.0009 0.0033 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Cl F I N O S
UNIT 28 16 4 12 4 4 4 4

L.S. 10
PLAN  10
SIZE 0.05 0.15 0.18
TEMP -173.15
BOND $H
list 4
fmap 2 53
acta
OMIT 0 0 2
REM <olex2.extras>
REM <HklSrc "%.\\jk181120_2.hkl">
REM </olex2.extras>

WGHT    0.012700    5.424000
FVAR       0.43216
I1    5    0.335907    0.433687    0.560818    11.00000    0.01686    0.01733 =
         0.01524   -0.00175   -0.00100   -0.00162
CL1   3    0.687327    0.466771    0.494877    11.00000    0.01882    0.02456 =
         0.02352   -0.00499    0.00380   -0.00026
S1    8    0.097185    0.576125    0.654943    11.00000    0.01619    0.02825 =
         0.01664    0.00030    0.00007    0.00020
F3    4    0.310947    0.601081    0.741950    11.00000    0.05024    0.03913 =
         0.02053   -0.00770   -0.01122    0.02036
F1    4    0.477190    0.392489    0.697174    11.00000    0.03461    0.02667 =
         0.03198   -0.00069   -0.00327    0.01190
O1    7   -0.122744    0.665473    0.676693    11.00000    0.01827    0.05031 =
         0.02007    0.00034    0.00315    0.00525
F2    4    0.098903    0.350111    0.727622    11.00000    0.05114    0.07550 =
         0.03817    0.02973   -0.00603   -0.02977
N1    6    0.062491    0.428160    0.617448    11.00000    0.02057    0.03650 =
         0.01322   -0.00205    0.00170   -0.00664
C7    1    0.257113    0.473364    0.708906    11.00000    0.02544    0.02116 =
         0.02110   -0.00267   -0.00184    0.00059
C2    1    0.330128    0.733957    0.633553    11.00000    0.01778    0.01763 =
         0.01604    0.00438    0.00335    0.00095
C6    1    0.643009    0.801130    0.571950    11.00000    0.02403    0.02116 =
         0.01654    0.00209    0.00003    0.00572
AFIX  43
H6    2    0.731909    0.768998    0.542966    11.00000   -1.20000
AFIX   0
C3    1    0.379416    0.900901    0.656903    11.00000    0.02440    0.02133 =
         0.02179   -0.00161   -0.00247    0.00584
AFIX  43
H3    2    0.285993    0.935410    0.685199    11.00000   -1.20000
AFIX   0
C5    1    0.696411    0.966367    0.596049    11.00000    0.02733    0.01554 =
         0.02918    0.00396   -0.00036   -0.00567
AFIX  43
H5    2    0.824861    1.047499    0.583311    11.00000   -1.20000
AFIX   0
C1    1    0.458824    0.686801    0.591311    11.00000    0.01494    0.01366 =
         0.01919   -0.00305   -0.00210    0.00139
C4    1    0.568153    1.014801    0.637700    11.00000    0.03701    0.01692 =
         0.02811   -0.00503   -0.00381    0.00349
AFIX  43
H4    2    0.609792    1.128006    0.653483    11.00000   -1.20000
AFIX   0
HKLF 4

REM  jk181120_2_a.res in P2(1)2(1)2(1)
REM R1 =  0.0321 for    2136 Fo > 4sig(Fo)  and  0.0328 for all    2177 data
REM    136 parameters refined using      0 restraints

END

WGHT      0.0127      5.4241

REM Highest difference peak  1.609,  deepest hole -1.492,  1-sigma level  0.147
Q1    1   0.3405  0.4350  0.5993  11.00000  0.05    1.61
Q2    1   0.3499  0.4362  0.5209  11.00000  0.05    1.32
Q3    1   0.0820  0.4339  0.5823  11.00000  0.05    0.78
Q4    1  -0.1432  0.8121  0.6810  11.00000  0.05    0.67
Q5    1   0.2744  0.3223  0.5595  11.00000  0.05    0.63
Q6    1  -0.0105  0.4991  0.5394  11.00000  0.05    0.61
Q7    1   1.0332  0.4519  0.4961  11.00000  0.05    0.56
Q8    1   0.4967  0.3746  0.5611  11.00000  0.05    0.53
Q9    1   0.0605  0.4372  0.5372  11.00000  0.05    0.53
Q10   1   0.7008  0.4259  0.5585  11.00000  0.05    0.50
;
_shelx_res_checksum              28744
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jk20190808_2
_database_code_depnum_ccdc_archive 'CCDC 1947035'
loop_
_audit_author_name
_audit_author_address
'Ewa Pietrasiak'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2019-10-07 downloaded from the CCDC.
;
_audit_creation_date             2019-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H4 F6 I N O S'
_chemical_formula_sum            'C8 H4 F6 I N O S'
_chemical_formula_weight         403.08
_chemical_melting_point          ?
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'

_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                   7.1787(13)
_cell_length_b                   10.1369(18)
_cell_length_c                   15.408(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.647(3)
_cell_angle_gamma                90
_cell_volume                     1120.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4891
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      28.77
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.604
_shelx_estimated_absorpt_T_min   0.510
_exptl_absorpt_coefficient_mu    3.113
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0642 before and 0.0535 after correction. The Ratio of minimum to maximum transmission is 0.9198. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 'DCM evaporation, inert atm'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20239
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_min         2.406
_diffrn_ambient_temperature      101.2
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART Apex2'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2445
_reflns_number_total             2788
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0220
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0127P)²+0.9249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0415
_refine_ls_wR_factor_ref         0.0433
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C4(H4)
;
_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
I1 I 0.18373(2) 0.47706(2) 0.61276(2) 0.01103(5) Uani 1 1 d . . . . .
S1 S 0.32287(8) 0.31733(6) 0.45054(4) 0.01160(13) Uani 1 1 d . . . . .
F1 F 0.1869(2) 0.10902(16) 0.53049(10) 0.0243(4) Uani 1 1 d . . . . .
F5 F 0.2319(2) 0.41397(16) 0.80648(10) 0.0238(4) Uani 1 1 d . . . . .
F6 F 0.0479(2) 0.57595(18) 0.77278(11) 0.0279(4) Uani 1 1 d . . . . .
F4 F 0.3456(2) 0.60618(17) 0.78179(10) 0.0271(4) Uani 1 1 d . . . . .
F2 F 0.3595(3) 0.05786(16) 0.42533(13) 0.0329(4) Uani 1 1 d . . . . .
O1 O 0.4205(2) 0.31818(18) 0.37080(11) 0.0159(4) Uani 1 1 d . . . . .
F3 F 0.0837(2) 0.13571(18) 0.39870(11) 0.0327(4) Uani 1 1 d . . . . .
N1 N 0.1715(3) 0.4101(2) 0.47104(14) 0.0164(5) Uani 1 1 d . . . . .
C1 C 0.4450(3) 0.3768(2) 0.61568(16) 0.0110(5) Uani 1 1 d . . . . .
C6 C 0.5703(3) 0.3786(2) 0.68640(17) 0.0141(5) Uani 1 1 d . . . . .
H6 H 0.5441 0.4266 0.7374 0.017 Uiso 1 1 calc R . . . .
C2 C 0.4860(3) 0.3111(2) 0.54032(16) 0.0113(5) Uani 1 1 d . . . . .
C8 C 0.2132(4) 0.5209(3) 0.75587(17) 0.0179(5) Uani 1 1 d . . . . .
C3 C 0.6540(3) 0.2436(2) 0.53454(17) 0.0143(5) Uani 1 1 d . . . . .
H3 H 0.6830 0.1997 0.4824 0.017 Uiso 1 1 calc R . . . .
C5 C 0.7357(3) 0.3085(3) 0.68103(17) 0.0156(5) Uani 1 1 d . . . . .
H5 H 0.8215 0.3062 0.7298 0.019 Uiso 1 1 calc R . . . .
C4 C 0.7778(4) 0.2418(3) 0.60590(18) 0.0165(6) Uani 1 1 d . . . . .
H4 H 0.8919 0.1947 0.6035 0.020 Uiso 1 1 calc R . . . .
C7 C 0.2350(4) 0.1446(3) 0.45140(17) 0.0174(6) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01019(8) 0.01195(8) 0.01087(8) -0.00078(6) -0.00054(5) 0.00068(6)
S1 0.0127(3) 0.0116(3) 0.0103(3) -0.0003(2) -0.0006(2) -0.0008(2)
F1 0.0325(9) 0.0236(9) 0.0170(8) 0.0032(7) 0.0034(7) -0.0109(7)
F5 0.0279(9) 0.0293(9) 0.0144(8) 0.0056(7) 0.0030(7) 0.0010(7)
F6 0.0242(9) 0.0384(11) 0.0215(9) -0.0072(8) 0.0061(7) 0.0093(8)
F4 0.0296(9) 0.0331(10) 0.0185(9) -0.0094(7) 0.0005(7) -0.0098(8)
F2 0.0419(11) 0.0121(9) 0.0462(12) -0.0073(8) 0.0178(9) -0.0028(7)
O1 0.0188(9) 0.0177(10) 0.0114(9) 0.0002(7) 0.0018(7) -0.0028(7)
F3 0.0355(10) 0.0350(11) 0.0261(9) 0.0017(8) -0.0137(8) -0.0190(8)
N1 0.0157(11) 0.0198(12) 0.0134(11) -0.0044(9) -0.0030(9) 0.0037(9)
C1 0.0100(11) 0.0079(12) 0.0149(13) 0.0041(10) -0.0008(9) -0.0020(9)
C6 0.0158(12) 0.0129(13) 0.0135(13) 0.0017(10) -0.0002(10) -0.0023(10)
C2 0.0112(11) 0.0106(13) 0.0120(12) 0.0016(10) -0.0006(9) -0.0013(9)
C8 0.0152(12) 0.0246(15) 0.0141(13) -0.0031(11) 0.0032(10) 0.0007(11)
C3 0.0156(12) 0.0103(13) 0.0173(13) 0.0006(10) 0.0023(10) -0.0017(10)
C5 0.0103(12) 0.0185(14) 0.0176(13) 0.0075(11) -0.0042(10) -0.0044(10)
C4 0.0119(12) 0.0139(14) 0.0237(15) 0.0050(11) -0.0001(11) 0.0004(10)
C7 0.0203(13) 0.0178(15) 0.0141(13) -0.0015(11) 0.0017(11) -0.0068(11)

_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
I1 N1 2.285(2) . ?
I1 C1 2.132(2) . ?
I1 C8 2.250(3) . ?
S1 O1 1.4424(18) . ?
S1 N1 1.482(2) . ?
S1 C2 1.772(2) . ?
S1 C7 1.861(3) . ?
F1 C7 1.332(3) . ?
F5 C8 1.338(3) . ?
F6 C8 1.347(3) . ?
F4 C8 1.333(3) . ?
F2 C7 1.329(3) . ?
F3 C7 1.329(3) . ?
C1 C6 1.380(3) . ?
C1 C2 1.382(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(3) . ?
C2 C3 1.393(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(4) . ?
C4 H4 0.9500 . ?

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
C1 I1 N1 82.73(8) . . ?
C1 I1 C8 91.76(9) . . ?
C8 I1 N1 173.33(9) . . ?
O1 S1 N1 124.59(12) . . ?
O1 S1 C2 109.62(11) . . ?
O1 S1 C7 100.94(11) . . ?
N1 S1 C2 108.72(12) . . ?
N1 S1 C7 110.08(13) . . ?
C2 S1 C7 99.94(12) . . ?
S1 N1 I1 113.34(11) . . ?
C6 C1 I1 123.41(19) . . ?
C6 C1 C2 120.9(2) . . ?
C2 C1 I1 115.67(17) . . ?
C1 C6 H6 120.9 . . ?
C1 C6 C5 118.2(2) . . ?
C5 C6 H6 120.9 . . ?
C1 C2 S1 118.70(18) . . ?
C1 C2 C3 120.6(2) . . ?
C3 C2 S1 120.71(19) . . ?
F5 C8 I1 114.43(18) . . ?
F5 C8 F6 106.8(2) . . ?
F6 C8 I1 103.16(16) . . ?
F4 C8 I1 117.09(17) . . ?
F4 C8 F5 107.4(2) . . ?
F4 C8 F6 107.2(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.9(2) . . ?
C4 C3 H3 120.6 . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.4 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
F1 C7 S1 111.31(18) . . ?
F2 C7 S1 112.81(18) . . ?
F2 C7 F1 107.7(2) . . ?
F2 C7 F3 108.2(2) . . ?
F3 C7 S1 109.09(19) . . ?
F3 C7 F1 107.5(2) . . ?

_shelx_res_file                  
;
    jk20190808_2.res created by SHELXL-2014/7

TITL jk20190808_2_a.res in P2(1)/n
REM Old TITL JK20190808_2 in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.046, Rweak 0.002, Alpha 0.046, Orientation as input
REM Formula found by SHELXT: C9 O F6 S I
CELL 0.71073 7.1787 10.1369 15.4082 90 92.647 90
ZERR 4 0.0013 0.0018 0.0028 0 0.003 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O F S I
UNIT 32 16 4 4 24 4 4

L.S. 10
PLAN  10
SIZE 0.18 0.22 0.25
TEMP -171.95
BOND $H
LIST 6
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\JK20190808_2.hkl">
REM </olex2.extras>

WGHT    0.012700    0.924900
FVAR       0.36054
I1    7    0.183733    0.477064    0.612760    11.00000    0.01019    0.01195 =
         0.01087   -0.00078   -0.00054    0.00068
S1    6    0.322871    0.317330    0.450542    11.00000    0.01272    0.01162 =
         0.01034   -0.00026   -0.00064   -0.00078
F1    5    0.186890    0.109024    0.530492    11.00000    0.03255    0.02358 =
         0.01697    0.00318    0.00340   -0.01093
F5    5    0.231906    0.413973    0.806482    11.00000    0.02793    0.02928 =
         0.01439    0.00562    0.00303    0.00102
F6    5    0.047940    0.575950    0.772775    11.00000    0.02420    0.03839 =
         0.02152   -0.00718    0.00610    0.00931
F4    5    0.345595    0.606178    0.781790    11.00000    0.02964    0.03308 =
         0.01847   -0.00937    0.00053   -0.00977
F2    5    0.359463    0.057860    0.425329    11.00000    0.04193    0.01214 =
         0.04621   -0.00725    0.01784   -0.00282
O1    4    0.420505    0.318183    0.370797    11.00000    0.01884    0.01768 =
         0.01140    0.00017    0.00180   -0.00284
F3    5    0.083714    0.135708    0.398703    11.00000    0.03547    0.03503 =
         0.02614    0.00173   -0.01371   -0.01897
N1    3    0.171512    0.410055    0.471035    11.00000    0.01573    0.01982 =
         0.01337   -0.00441   -0.00302    0.00375
C1    1    0.445028    0.376838    0.615681    11.00000    0.00996    0.00786 =
         0.01495    0.00410   -0.00077   -0.00205
C6    1    0.570264    0.378646    0.686402    11.00000    0.01580    0.01287 =
         0.01353    0.00165   -0.00018   -0.00231
AFIX  43
H6    2    0.544078    0.426580    0.737399    11.00000   -1.20000
AFIX   0
C2    1    0.485974    0.311079    0.540321    11.00000    0.01119    0.01058 =
         0.01205    0.00164   -0.00057   -0.00131
C8    1    0.213178    0.520886    0.755871    11.00000    0.01520    0.02462 =
         0.01411   -0.00314    0.00323    0.00075
C3    1    0.653999    0.243650    0.534540    11.00000    0.01562    0.01025 =
         0.01728    0.00059    0.00230   -0.00172
AFIX  43
H3    2    0.682990    0.199686    0.482412    11.00000   -1.20000
AFIX   0
C5    1    0.735679    0.308490    0.681033    11.00000    0.01029    0.01855 =
         0.01763    0.00750   -0.00415   -0.00435
AFIX  43
H5    2    0.821548    0.306212    0.729807    11.00000   -1.20000
AFIX   0
C4    1    0.777786    0.241785    0.605897    11.00000    0.01190    0.01393 =
         0.02370    0.00497   -0.00012    0.00040
AFIX  43
H4    2    0.891878    0.194738    0.603465    11.00000   -1.20000
AFIX   0
C7    1    0.235040    0.144588    0.451395    11.00000    0.02026    0.01782 =
         0.01414   -0.00155    0.00171   -0.00676
HKLF 4

REM  jk20190808_2_a.res in P2(1)/n
REM R1 =  0.0220 for    2445 Fo > 4sig(Fo)  and  0.0276 for all    2788 data
REM    163 parameters refined using      0 restraints

END

WGHT      0.0127      0.9250

REM Highest difference peak  0.576,  deepest hole -0.455,  1-sigma level  0.106
Q1    1   0.2882  0.2248  0.4575  11.00000  0.05    0.58
Q2    1   0.2200  0.3374  0.4800  11.00000  0.05    0.51
Q3    1   0.6831  0.2290  0.5852  11.00000  0.05    0.44
Q4    1   0.4512  0.3050  0.5822  11.00000  0.05    0.43
Q5    1   0.5534  0.2634  0.5568  11.00000  0.05    0.41
Q6    1   0.4321  0.2953  0.5007  11.00000  0.05    0.40
Q7    1   0.5025  0.3450  0.6587  11.00000  0.05    0.40
Q8    1   0.8018  0.2999  0.6365  11.00000  0.05    0.40
Q9    1   0.5199  0.4053  0.6403  11.00000  0.05    0.38
Q10   1   0.0679  0.4787  0.6390  11.00000  0.05    0.38
;
_shelx_res_checksum              88962
_olex2_date_sample_data_collection 2019-08-08
_olex2_date_sample_submission    2019-08-08
_olex2_submission_special_instructions 'No special instructions were received'
