# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1908422'
loop_
_audit_author_name
_audit_author_address
'Victor Nemykin'
;University of Manitoba
Canada
;
_audit_update_record             
;
2019-04-06 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   15.4493(5)
_cell_length_b                   5.7324(2)
_cell_length_c                   20.1514(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.086(7)
_cell_angle_gamma                90
_cell_volume                     1771.01(12)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C8 H6 F3 I1 O7 S1 
# Dc =      1.61 Fooo =   1160.00 Mu =    158.14 M =    430.10
# Found Formula = C9 H9 F6 I1 O11 S2 
# Dc =      2.24 FOOO =   1160.00 Mu =    175.69 M =    598.19

_chemical_formula_sum            'C9 H9 F6 I1 O11 S2'
_chemical_formula_moiety         'C9 H9 F6 I1 O11 S2'
_chemical_compound_source        ?
_chemical_formula_weight         598.19


_cell_measurement_reflns_used    8356
_cell_measurement_theta_min      3
_cell_measurement_theta_max      68
_cell_measurement_temperature    123

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.040
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_max          0.110

_exptl_crystal_density_diffrn    2.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    17.569

# Sheldrick geometric approximatio 0.35 0.50 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.14
_exptl_absorpt_correction_T_max  0.50
_diffrn_measurement_device_type  'Image Plate'
_diffrn_measurement_device       'Rigaku RAPID-II'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  2
_diffrn_standards_interval_count .
_diffrn_standards_number         8356
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      123
_diffrn_reflns_number            8356
_reflns_number_total             2811
_diffrn_reflns_av_R_equivalents  0.098
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2811 
# Theoretical number of reflections is about 6476 


_diffrn_reflns_theta_min         3.409
_diffrn_reflns_theta_max         68.171
_diffrn_measured_fraction_theta_max 0.870

_diffrn_reflns_theta_full        25.223
_diffrn_measured_fraction_theta_full 0.962


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -18
_reflns_limit_h_max              18
_reflns_limit_k_min              0
_reflns_limit_k_max              6
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_oxford_diffrn_Wilson_B_factor   2.73
_oxford_diffrn_Wilson_scale      2.85

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -2.62
_refine_diff_density_max         6.17


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         2746
_refine_ls_number_restraints     13
_refine_ls_number_parameters     277
_oxford_refine_ls_R_factor_ref   0.1213
_refine_ls_wR_factor_ref         0.2581
_refine_ls_goodness_of_fit_ref   0.9094
_refine_ls_shift/su_max          0.0005036
_refine_ls_shift/su_mean         0.0000112


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2746
_refine_ls_R_factor_all          0.1213
_refine_ls_wR_factor_all         0.2581

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1810
_refine_ls_R_factor_gt           0.0953
_refine_ls_wR_factor_gt          0.2256

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.13P)² +40.86P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
I1 I 0.65031(6) 0.02495(17) 0.25324(5) 0.0392 1.0000 Uani D . . . . .
O2 O 0.6382(6) -0.2496(18) 0.3024(5) 0.0419 1.0000 Uani D . . . . .
O3 O 0.6422(6) 0.3175(19) 0.1691(5) 0.0427 1.0000 Uani . . . . . .
C7 C 0.5865(9) 0.268(3) 0.1210(8) 0.0427 1.0000 Uani D . . . . .
O4 O 0.5768(7) 0.383(2) 0.0657(6) 0.0510 1.0000 Uani D . . . . .
C2 C 0.5279(9) 0.070(3) 0.1273(8) 0.0424 1.0000 Uani . . . . . .
C1 C 0.5449(9) -0.073(2) 0.1826(7) 0.0335 1.0000 Uani . . . . . .
C6 C 0.4942(8) -0.256(3) 0.1921(8) 0.0387 1.0000 Uani . . . . . .
C5 C 0.4223(10) -0.308(3) 0.1430(9) 0.0562 1.0000 Uani . . . . . .
C4 C 0.4053(9) -0.173(3) 0.0876(8) 0.0425 1.0000 Uani . . . . . .
C3 C 0.4584(12) 0.016(3) 0.0787(9) 0.0501 1.0000 Uani . . . . . .
O1 O 0.7395(7) -0.0737(19) 0.2118(5) 0.0461 1.0000 Uani . . . . . .
S1 S 0.7348(2) 0.2893(7) 0.4449(2) 0.0415 1.0000 Uani . . . . . .
O5 O 0.6813(7) 0.1478(19) 0.3982(5) 0.0482 1.0000 Uani . . . . . .
O6 O 0.8283(6) 0.2453(18) 0.4493(5) 0.0437 1.0000 Uani . . . . . .
O7 O 0.7152(8) 0.5379(19) 0.4435(7) 0.0560 1.0000 Uani . . . . . .
C8 C 0.7061(10) 0.196(3) 0.5239(7) 0.0409 1.0000 Uani . . . . . .
F3 F 0.7193(8) -0.0331(18) 0.5344(5) 0.0675 1.0000 Uani . . . . . .
F2 F 0.7529(7) 0.303(2) 0.5753(5) 0.0699 1.0000 Uani . . . . . .
F1 F 0.6228(6) 0.2348(17) 0.5290(5) 0.0577 1.0000 Uani . . . . . .
S2 S 0.4606(2) 0.1987(7) 0.3398(2) 0.0440 1.0000 Uani . . . . . .
O8 O 0.4710(8) -0.050(2) 0.3442(7) 0.0594 1.0000 Uani . . . . . .
O10 O 0.4605(7) 0.314(2) 0.4033(6) 0.0524 1.0000 Uani . . . . . .
O9 O 0.5158(7) 0.300(2) 0.2952(6) 0.0549 1.0000 Uani . . . . . .
C9 C 0.3506(11) 0.243(3) 0.2997(9) 0.0479 1.0000 Uani . . . . . .
F5 F 0.3449(6) 0.156(2) 0.2370(5) 0.0724 1.0000 Uani . . . . . .
F6 F 0.3348(7) 0.468(2) 0.2911(6) 0.0766 1.0000 Uani . . . . . .
F4 F 0.2924(7) 0.146(3) 0.3294(6) 0.1015 1.0000 Uani . . . . . .
O11 O 0.5551(7) 0.678(2) 0.4333(5) 0.0502 1.0000 Uani D . . . . .
H4 H 0.5066 -0.3486 0.2300 0.0581 1.0000 Uiso R . . . . .
H3 H 0.3860 -0.4329 0.1496 0.0672 1.0000 Uiso R . . . . .
H2 H 0.3592 -0.2098 0.0552 0.0612 1.0000 Uiso R . . . . .
H1 H 0.4476 0.1093 0.0407 0.0672 1.0000 Uiso R . . . . .
H8 H 0.519(6) 0.578(15) 0.421(7) 0.0635 1.0000 Uiso D . . . . .
H9 H 0.545(7) 0.790(16) 0.408(6) 0.0500 1.0000 Uiso D . . . . .
H7 H 0.603(4) 0.625(18) 0.427(6) 0.0500 1.0000 Uiso D . . . . .
H5 H 0.682(5) -0.328(13) 0.301(7) 0.0500 1.0000 Uiso D . . . . .
H6 H 0.607(10) 0.501(17) 0.071(3) 0.0603 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.579(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 . O2 . 1.881(10) yes
I1 . O3 . 2.377(10) yes
I1 . C1 . 2.102(11) yes
I1 . O1 . 1.790(12) yes
O2 . H5 . 0.82(2) no
O3 . C7 . 1.248(16) yes
C7 . O4 . 1.288(18) yes
C7 . C2 . 1.47(2) yes
O4 . H6 . 0.82(2) no
C2 . C1 . 1.38(2) yes
C2 . C3 . 1.39(2) yes
C1 . C6 . 1.34(2) yes
C6 . C5 . 1.426(18) yes
C6 . H4 . 0.930 no
C5 . C4 . 1.36(2) yes
C5 . H3 . 0.930 no
C4 . C3 . 1.39(2) yes
C4 . H2 . 0.930 no
C3 . H1 . 0.930 no
S1 . O5 . 1.427(11) yes
S1 . O6 . 1.459(10) yes
S1 . O7 . 1.457(11) yes
S1 . C8 . 1.786(17) yes
C8 . F3 . 1.342(18) yes
C8 . F2 . 1.337(16) yes
C8 . F1 . 1.322(16) yes
S2 . O8 . 1.437(12) yes
S2 . O10 . 1.441(11) yes
S2 . O9 . 1.435(13) yes
S2 . C9 . 1.807(16) yes
C9 . F5 . 1.353(19) yes
C9 . F6 . 1.319(18) yes
C9 . F4 . 1.27(2) yes
O11 . H8 . 0.82(2) no
O11 . H9 . 0.82(2) no
O11 . H7 . 0.82(2) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . I1 . O3 . 165.0(4) yes
O2 . I1 . C1 . 90.8(5) yes
O3 . I1 . C1 . 74.7(5) yes
O2 . I1 . O1 . 96.5(5) yes
O3 . I1 . O1 . 82.3(4) yes
C1 . I1 . O1 . 100.2(5) yes
I1 . O2 . H5 . 108.000(10) no
I1 . O3 . C7 . 111.4(11) yes
O3 . C7 . O4 . 123.4(15) yes
O3 . C7 . C2 . 118.8(15) yes
O4 . C7 . C2 . 117.7(12) yes
C7 . O4 . H6 . 108.000(11) no
C7 . C2 . C1 . 118.0(13) yes
C7 . C2 . C3 . 122.6(15) yes
C1 . C2 . C3 . 119.4(15) yes
I1 . C1 . C2 . 116.4(11) yes
I1 . C1 . C6 . 122.0(11) yes
C2 . C1 . C6 . 121.5(12) yes
C1 . C6 . C5 . 119.0(15) yes
C1 . C6 . H4 . 120.1 no
C5 . C6 . H4 . 120.9 no
C6 . C5 . C4 . 120.5(16) yes
C6 . C5 . H3 . 119.7 no
C4 . C5 . H3 . 119.8 no
C5 . C4 . C3 . 119.7(14) yes
C5 . C4 . H2 . 120.3 no
C3 . C4 . H2 . 119.9 no
C2 . C3 . C4 . 119.8(16) yes
C2 . C3 . H1 . 119.7 no
C4 . C3 . H1 . 120.5 no
O5 . S1 . O6 . 115.4(6) yes
O5 . S1 . O7 . 116.2(7) yes
O6 . S1 . O7 . 111.8(7) yes
O5 . S1 . C8 . 103.4(7) yes
O6 . S1 . C8 . 104.4(7) yes
O7 . S1 . C8 . 103.7(8) yes
S1 . C8 . F3 . 112.5(11) yes
S1 . C8 . F2 . 112.5(12) yes
F3 . C8 . F2 . 105.7(13) yes
S1 . C8 . F1 . 111.7(11) yes
F3 . C8 . F1 . 106.4(13) yes
F2 . C8 . F1 . 107.6(13) yes
O8 . S2 . O10 . 114.4(8) yes
O8 . S2 . O9 . 111.6(8) yes
O10 . S2 . O9 . 115.9(7) yes
O8 . S2 . C9 . 105.0(8) yes
O10 . S2 . C9 . 103.2(8) yes
O9 . S2 . C9 . 105.2(8) yes
S2 . C9 . F5 . 108.4(11) yes
S2 . C9 . F6 . 110.2(13) yes
F5 . C9 . F6 . 104.4(15) yes
S2 . C9 . F4 . 114.1(13) yes
F5 . C9 . F4 . 108.0(16) yes
F6 . C9 . F4 . 111.2(16) yes
H8 . O11 . H9 . 107.000(9) no
H8 . O11 . H7 . 107.000(7) no
H9 . O11 . H7 . 107.000(8) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H4 . O9 1_545 157.1(4) 0.930 2.402 3.28(2) yes
C3 . H1 . O6 3_454 144.3(5) 0.930 2.579 3.38(2) yes
O11 . H8 . O10 . 166(12) 0.823 1.771 2.58(2) yes
O11 . H9 . O8 1_565 150(12) 0.822 1.857 2.60(2) yes
O11 . H7 . O7 . 160(12) 0.823 1.795 2.59(2) yes
O2 . H5 . O1 4_645 164(14) 0.816 1.895 2.69(2) yes
O4 . H6 . O6 4_655 159(9) 0.819 1.798 2.58(2) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
4 3 16 x .
4 4 13 x .
3 0 19 x .
3 5 13 x .
-12 3 15 x .
3 3 16 x .
-2 3 21 x .
2 5 11 x .
-7 3 18 x .
-7 3 18 x .
-6 3 11 x .
-2 1 23 x .
-3 2 21 x .
-3 3 20 x .
-1 6 2 x .
4 5 13 x .
3 3 18 x .
2 4 13 x .
-4 6 3 x .
3 5 15 x .
-8 3 15 x .
1 4 13 x .
-7 5 15 x .
-8 4 14 x .
-1 5 9 x .
5 4 15 x .
-5 4 12 x .
-5 6 4 x .
4 6 1 x .
6 6 1 x .
-8 3 8 x .
-8 3 8 x .
-8 3 8 x .
-9 3 13 x .
-14 3 7 x .
-8 3 8 x .
-8 3 8 x .
-8 3 8 x .
6 6 3 x .
-5 4 19 x .
-13 3 8 x .
3 3 12 x .
2 4 16 x .
-7 3 13 x .
-6 4 18 x .
0 5 15 x .
4 3 18 x .
-8 3 17 x .
-2 1 23 x .
3 4 16 x .
3 3 17 x .
5 3 17 x .
4 4 15 x .
4 4 14 x .
-6 4 11 x .
-1 1 23 x .
1 0 19 x .
2 4 14 x .
-6 3 14 x .
7 6 6 x .
-6 4 10 x .
16 1 0 x .
-8 3 16 x .
-4 6 1 x .
3 4 12 x .
2 5 15 x .
-1 6 4 x .
4 6 0 x .
