# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1047273'
_audit_update_record             
;
2015-02-03 deposited with the CCDC.
2015-04-01 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                   5.4618(6)
_cell_length_b                   9.7781(11)
_cell_length_c                   11.8765(13)
_cell_angle_alpha                98.200(7)
_cell_angle_beta                 93.463(7)
_cell_angle_gamma                91.657(7)
_cell_volume                     626.19(12)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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 0.0033 0.0016 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 0.0171 0.0103 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 -0.4742 1.8119 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 0.0106 0.0060 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 0.1246 0.1234 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            2

# Given Formula = C8 H4 F3 I1 O5 S1 
# Dc =      2.10 Fooo =    396.00 Mu =     27.70 M =    396.08
# Found Formula = C8 H6 F3 I1 O6 S1 
# Dc =      2.20 FOOO =    396.00 Mu =     27.81 M =    414.10

_chemical_formula_sum            'C8 H6 F3 I1 O6 S1'
_chemical_formula_moiety         'C8 H6 F3 I1 O6 S1'
_chemical_compound_source        ?
_chemical_formula_weight         414.10


_cell_measurement_reflns_used    4879
_cell_measurement_theta_min      2
_cell_measurement_theta_max      27
_cell_measurement_temperature    123

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_max          0.120

_exptl_crystal_density_diffrn    2.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    2.781

# Sheldrick geometric approximatio 0.80 0.87 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.87
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_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    'SHELXS 86 (Sheldrick, 1986)'
_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         4879
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      123
_diffrn_reflns_number            4879
_reflns_number_total             2283
_diffrn_reflns_av_R_equivalents  0.101
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2283 
# Theoretical number of reflections is about 4578 


_diffrn_reflns_theta_min         3.474
_diffrn_reflns_theta_max         25.333
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        25.333
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              -11
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -4.04
_refine_diff_density_max         3.77


# 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         2256
_refine_ls_number_restraints     0
_refine_ls_number_parameters     172
_oxford_refine_ls_R_factor_ref   0.1351
_refine_ls_wR_factor_ref         0.2099
_refine_ls_goodness_of_fit_ref   0.9851
_refine_ls_shift/su_max          0.0001059
_refine_ls_shift/su_mean         0.0000048


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2256
_refine_ls_R_factor_all          0.1351
_refine_ls_wR_factor_all         0.2099

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1414
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_gt          0.1541

# 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    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 126. 155. 47.9 
;

# 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 0.4980(3) 0.23921(14) 0.47574(11) 0.0405 1.0000 Uani . . . . . .
O2 O 0.304(2) 0.0722(13) 0.3354(10) 0.0420 1.0000 Uani . . . . . .
C7 C 0.396(4) 0.068(2) 0.2432(14) 0.0424 1.0000 Uani . . . . . .
O3 O 0.318(2) -0.0078(14) 0.1481(10) 0.0396 1.0000 Uani . . . . . .
C6 C 0.610(3) 0.164(2) 0.2328(16) 0.0362 1.0000 Uani . . . . . .
C1 C 0.691(3) 0.2501(18) 0.3324(15) 0.0373 1.0000 Uani . . . . . .
C2 C 0.887(4) 0.345(2) 0.3335(17) 0.0445 1.0000 Uani . . . . . .
C3 C 1.008(3) 0.3441(19) 0.2306(15) 0.0368 1.0000 Uani . . . . . .
C4 C 0.935(4) 0.2550(19) 0.1337(17) 0.0430 1.0000 Uani . . . . . .
C5 C 0.731(4) 0.162(2) 0.1328(16) 0.0420 1.0000 Uani . . . . . .
O1 O 0.685(2) 0.3931(11) 0.5613(10) 0.0393 1.0000 Uani . . . . . .
S1 S 0.1768(9) 0.2387(5) 0.7700(4) 0.0384 1.0000 Uani . . . . . .
O4 O 0.348(3) 0.1711(14) 0.6911(12) 0.0520 1.0000 Uani . . . . . .
O6 O 0.086(3) 0.1518(13) 0.8462(11) 0.0440 1.0000 Uani . . . . . .
O5 O -0.009(3) 0.3178(16) 0.7209(13) 0.0613 1.0000 Uani . . . . . .
C8 C 0.364(3) 0.3658(19) 0.8644(15) 0.0350 1.0000 Uani . . . . . .
F3 F 0.543(2) 0.3080(12) 0.9183(10) 0.0568 1.0000 Uani . . . . . .
F1 F 0.463(2) 0.4607(12) 0.8094(10) 0.0501 1.0000 Uani . . . . . .
F2 F 0.230(2) 0.4339(12) 0.9448(10) 0.0570 1.0000 Uani . . . . . .
H21 H 0.9338 0.4092 0.3969 0.0532 1.0000 Uiso R . . . . .
H31 H 1.1484 0.3998 0.2291 0.0571 1.0000 Uiso R . . . . .
H41 H 1.0188 0.2571 0.0679 0.0521 1.0000 Uiso R . . . . .
H51 H 0.6790 0.1015 0.0676 0.0540 1.0000 Uiso R . . . . .
H11 H 0.6758 0.3884 0.6293 0.0564 1.0000 Uiso R . . . . .
H32 H 0.2041 -0.0583 0.1612 0.0552 1.0000 Uiso 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 0.0479(8) 0.0437(7) 0.0316(6) 0.0102(5) 0.0046(5) 0.0026(5)
O2 0.056(9) 0.039(8) 0.036(7) 0.015(6) 0.016(6) 0.006(6)
C7 0.062(13) 0.050(12) 0.019(9) 0.011(8) 0.015(9) 0.016(10)
O3 0.046(8) 0.048(8) 0.026(6) 0.007(6) 0.008(5) -0.006(6)
C6 0.028(9) 0.043(11) 0.039(10) 0.009(8) 0.003(8) 0.008(8)
C1 0.045(11) 0.029(10) 0.039(10) 0.021(8) -0.016(9) -0.002(8)
C2 0.052(13) 0.042(11) 0.040(11) 0.008(9) -0.005(9) 0.011(9)
C3 0.040(11) 0.038(10) 0.038(10) 0.021(8) 0.007(8) -0.006(8)
C4 0.050(12) 0.033(10) 0.050(12) 0.009(9) 0.021(10) 0.003(9)
C5 0.052(12) 0.051(12) 0.030(10) 0.023(9) 0.010(9) 0.005(10)
O1 0.066(9) 0.021(6) 0.031(7) 0.009(5) 0.000(6) -0.006(6)
S1 0.044(3) 0.041(3) 0.032(2) 0.014(2) 0.002(2) -0.002(2)
O4 0.058(9) 0.047(9) 0.050(9) -0.001(7) 0.019(7) -0.001(7)
O6 0.063(9) 0.032(7) 0.038(7) 0.010(6) 0.002(6) -0.014(6)
O5 0.051(9) 0.062(10) 0.073(11) 0.026(8) -0.019(8) 0.002(8)
C8 0.043(11) 0.033(10) 0.029(9) 0.011(8) -0.008(8) -0.003(8)
F3 0.065(8) 0.047(7) 0.057(7) 0.012(6) -0.019(6) -0.002(6)
F1 0.057(7) 0.045(7) 0.052(7) 0.023(5) 0.005(6) -0.012(6)
F2 0.067(8) 0.052(7) 0.050(7) 0.000(6) 0.018(6) -0.011(6)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.839(6)
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 . 2.340(13) yes
I1 . C1 . 2.069(19) yes
I1 . O1 . 1.921(12) yes
O2 . C7 . 1.23(2) yes
C7 . O3 . 1.30(2) yes
C7 . C6 . 1.50(3) yes
O3 . H32 . 0.820 no
C6 . C1 . 1.39(2) yes
C6 . C5 . 1.39(2) yes
C1 . C2 . 1.40(3) yes
C2 . C3 . 1.42(3) yes
C2 . H21 . 0.927 no
C3 . C4 . 1.37(3) yes
C3 . H31 . 0.929 no
C4 . C5 . 1.42(3) yes
C4 . H41 . 0.933 no
C5 . H51 . 0.928 no
O1 . H11 . 0.820 no
S1 . O4 . 1.466(14) yes
S1 . O6 . 1.427(12) yes
S1 . O5 . 1.440(14) yes
S1 . C8 . 1.798(18) yes
C8 . F3 . 1.32(2) yes
C8 . F1 . 1.330(19) yes
C8 . F2 . 1.35(2) yes
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 . C1 . 75.3(6) yes
O2 . I1 . O1 . 166.8(5) yes
C1 . I1 . O1 . 92.2(6) yes
I1 . O2 . C7 . 112.6(13) yes
O2 . C7 . O3 . 127(2) yes
O2 . C7 . C6 . 119.0(18) yes
O3 . C7 . C6 . 114.2(15) yes
C7 . O3 . H32 . 108.2 no
C7 . C6 . C1 . 115.5(16) yes
C7 . C6 . C5 . 122.6(17) yes
C1 . C6 . C5 . 121.8(19) yes
C6 . C1 . I1 . 117.5(13) yes
C6 . C1 . C2 . 120.9(18) yes
I1 . C1 . C2 . 121.5(14) yes
C1 . C2 . C3 . 117.2(18) yes
C1 . C2 . H21 . 122.2 no
C3 . C2 . H21 . 120.5 no
C2 . C3 . C4 . 121.7(18) yes
C2 . C3 . H31 . 120.2 no
C4 . C3 . H31 . 117.9 no
C3 . C4 . C5 . 120.5(17) yes
C3 . C4 . H41 . 119.4 no
C5 . C4 . H41 . 120.1 no
C4 . C5 . C6 . 117.7(19) yes
C4 . C5 . H51 . 121.3 no
C6 . C5 . H51 . 121.0 no
I1 . O1 . H11 . 108.1 no
O4 . S1 . O6 . 113.8(9) yes
O4 . S1 . O5 . 116.1(9) yes
O6 . S1 . O5 . 113.7(9) yes
O4 . S1 . C8 . 104.7(9) yes
O6 . S1 . C8 . 102.4(8) yes
O5 . S1 . C8 . 104.1(9) yes
S1 . C8 . F3 . 111.3(13) yes
S1 . C8 . F1 . 112.1(12) yes
F3 . C8 . F1 . 108.2(15) yes
S1 . C8 . F2 . 111.2(13) yes
F3 . C8 . F2 . 107.0(14) yes
F1 . C8 . F2 . 106.8(15) yes
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
C5 . H51 . O3 2_655 153.3(5) 0.928 2.596 3.45(3) yes
O3 . H32 . O6 2_556 163.4(6) 0.820 1.797 2.59(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 26/01/15 at 16:28:41
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE O   (   3,X'S) H   (  32,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE O   (   1,X'S) H   (  11,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 26/01/15 at 16:28:41
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# 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
1 -5 12 x .
1 -7 11 x .
-3 -2 8 x .
0 -5 13 x .
0 -10 7 x .
0 -10 6 x .
1 -5 12 x .
2 -5 12 x .
0 -8 8 x .
-6 -2 4 x .
-3 8 1 x .
0 7 4 x .
-2 8 0 x .
2 -6 10 x .
1 -7 10 x .
2 -7 9 x .
3 1 11 x .
-2 8 0 x .
-3 8 0 x .
0 -10 8 x .
2 -4 12 x .
3 -10 3 x .
-1 9 5 x .
3 -10 1 x .
-2 7 0 x .
0 -10 8 x .
0 7 4 x .
2 -5 11 x .
2 -4 12 x .
