# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 I N O2, B F4'
_chemical_formula_sum            'C12 H9 B F4 I N O2'
_chemical_formula_weight         412.91

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'
B B 0.0013 0.0007 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   16.725(8)
_cell_length_b                   10.562(5)
_cell_length_c                   16.707(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.932(8)
_cell_angle_gamma                90.00
_cell_volume                     2738(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4769
_cell_measurement_theta_min      1.3139
_cell_measurement_theta_max      30.7181

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_absorpt_coefficient_mu    2.388
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9081
_exptl_absorpt_process_details   
;
Abscor. T. Higashi. (2001). Rigaku Corp. Tokyo, Japan
;


_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(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  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19955
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2418
_reflns_number_gt                2415
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_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)+(0.0300P)²+20.4034P] 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         2418
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_restrained_S_all      1.249
_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
I1 I 0.220888(18) 0.10247(3) 0.138144(19) 0.01792(13) Uani 1 1 d . . .
O1 O -0.1289(2) 0.4289(4) 0.1653(3) 0.0305(9) Uani 1 1 d . . .
O2 O -0.0893(2) 0.5685(3) 0.0919(3) 0.0303(9) Uani 1 1 d . . .
N1 N -0.0821(3) 0.4651(4) 0.1271(3) 0.0232(9) Uani 1 1 d . . .
C1 C 0.3054(3) 0.1807(4) 0.2560(3) 0.0159(9) Uani 1 1 d . . .
C2 C 0.3804(3) 0.2364(4) 0.2568(3) 0.0205(10) Uani 1 1 d . . .
H2 H 0.3940 0.2373 0.2077 0.025 Uiso 1 1 calc R . .
C3 C 0.4353(3) 0.2916(5) 0.3340(3) 0.0223(10) Uani 1 1 d . . .
H3 H 0.4869 0.3286 0.3372 0.027 Uiso 1 1 calc R . .
C4 C 0.4125(3) 0.2907(5) 0.4060(3) 0.0243(11) Uani 1 1 d . . .
H4 H 0.4487 0.3285 0.4570 0.029 Uiso 1 1 calc R . .
C5 C 0.3365(3) 0.2344(5) 0.4029(3) 0.0221(11) Uani 1 1 d . . .
H5 H 0.3221 0.2350 0.4516 0.027 Uiso 1 1 calc R . .
C6 C 0.2812(3) 0.1766(5) 0.3271(3) 0.0225(11) Uani 1 1 d . . .
H6 H 0.2305 0.1371 0.3244 0.027 Uiso 1 1 calc R . .
C7 C 0.1172(3) 0.2226(5) 0.1300(3) 0.0183(10) Uani 1 1 d . . .
C8 C 0.1212(3) 0.3498(5) 0.1078(3) 0.0215(10) Uani 1 1 d . . .
H8 H 0.1672 0.3803 0.0950 0.026 Uiso 1 1 calc R . .
C9 C 0.0543(3) 0.4285(5) 0.1058(3) 0.0222(10) Uani 1 1 d . . .
H9 H 0.0543 0.5134 0.0911 0.027 Uiso 1 1 calc R . .
C10 C -0.0126(3) 0.3792(5) 0.1258(3) 0.0194(10) Uani 1 1 d . . .
C11 C -0.0176(3) 0.2528(5) 0.1464(3) 0.0189(10) Uani 1 1 d . . .
H11 H -0.0643 0.2227 0.1581 0.023 Uiso 1 1 calc R . .
C12 C 0.0494(3) 0.1725(5) 0.1489(3) 0.0191(10) Uani 1 1 d . . .
H12 H 0.0487 0.0874 0.1630 0.023 Uiso 1 1 calc R . .
F1 F 0.40363(18) 0.4555(3) 0.03319(18) 0.0273(7) Uani 1 1 d . . .
F2 F 0.2919(2) 0.5734(3) 0.0368(2) 0.0434(9) Uani 1 1 d . . .
F3 F 0.3949(2) 0.5043(3) 0.16353(18) 0.0290(7) Uani 1 1 d . . .
F4 F 0.3003(2) 0.3652(3) 0.0727(2) 0.0367(8) Uani 1 1 d . . .
B1 B 0.3475(4) 0.4745(6) 0.0775(4) 0.0219(12) Uani 1 1 d . . .


_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 C7 2.112(5) . ?
I1 C1 2.116(4) . ?
O1 N1 1.240(6) . ?
O2 N1 1.224(6) . ?
N1 C10 1.482(6) . ?
C1 C2 1.381(7) . ?
C1 C6 1.393(7) . ?
C2 C3 1.401(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.401(7) . ?
C7 C12 1.392(7) . ?
C8 C9 1.384(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(7) . ?
C11 C12 1.393(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
F1 B1 1.410(6) . ?
F2 B1 1.394(7) . ?
F3 B1 1.394(6) . ?
F4 B1 1.384(7) . ?

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 I1 C1 94.15(17) . . ?
O2 N1 O1 123.7(4) . . ?
O2 N1 C10 118.4(4) . . ?
O1 N1 C10 117.9(4) . . ?
C2 C1 C6 123.9(4) . . ?
C2 C1 I1 117.7(3) . . ?
C6 C1 I1 118.4(3) . . ?
C1 C2 C3 117.9(4) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.9(5) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.0(5) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C8 C7 C12 123.2(4) . . ?
C8 C7 I1 118.3(3) . . ?
C12 C7 I1 118.4(3) . . ?
C9 C8 C7 117.7(4) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
C10 C9 C8 119.2(5) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 123.4(5) . . ?
C11 C10 N1 117.7(4) . . ?
C9 C10 N1 118.9(4) . . ?
C10 C11 C12 118.2(4) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C11 C12 C7 118.4(4) . . ?
C11 C12 H12 120.8 . . ?
C7 C12 H12 120.8 . . ?
F4 B1 F3 109.9(4) . . ?
F4 B1 F2 109.6(5) . . ?
F3 B1 F2 110.6(4) . . ?
F4 B1 F1 109.2(4) . . ?
F3 B1 F1 109.8(4) . . ?
F2 B1 F1 107.7(4) . . ?

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
C7 I1 C1 C2 -119.3(4) . . . . ?
C7 I1 C1 C6 58.8(4) . . . . ?
C6 C1 C2 C3 0.2(7) . . . . ?
I1 C1 C2 C3 178.2(3) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C2 C3 C4 C5 0.9(8) . . . . ?
C3 C4 C5 C6 0.3(8) . . . . ?
C2 C1 C6 C5 0.9(7) . . . . ?
I1 C1 C6 C5 -177.1(3) . . . . ?
C4 C5 C6 C1 -1.1(7) . . . . ?
C1 I1 C7 C8 73.8(4) . . . . ?
C1 I1 C7 C12 -104.6(4) . . . . ?
C12 C7 C8 C9 0.6(7) . . . . ?
I1 C7 C8 C9 -177.7(4) . . . . ?
C7 C8 C9 C10 0.3(7) . . . . ?
C8 C9 C10 C11 -1.5(8) . . . . ?
C8 C9 C10 N1 177.4(4) . . . . ?
O2 N1 C10 C11 -164.5(4) . . . . ?
O1 N1 C10 C11 16.7(6) . . . . ?
O2 N1 C10 C9 16.5(7) . . . . ?
O1 N1 C10 C9 -162.3(5) . . . . ?
C9 C10 C11 C12 1.6(7) . . . . ?
N1 C10 C11 C12 -177.3(4) . . . . ?
C10 C11 C12 C7 -0.6(7) . . . . ?
C8 C7 C12 C11 -0.5(7) . . . . ?
I1 C7 C12 C11 177.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.120

_iucr_refine_instruction_details 
;
TITL owkm001                     New: C2/c
CELL  0.71073  16.7250  10.5620  16.7070   90.000  111.932   90.000
ZERR     8.00   0.0083   0.0045   0.0079    0.000    0.0083    0.000
LATT   7
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    B    F    I    N    O
UNIT  96   72   8    32   8    8    16
MERG   2
FMAP   2
ACTA
BOND   $H
CONF
LIST 4
OMIT   -4 50
L.S.   10
WGHT    0.030000   20.403400
FVAR       1.47728
I1    5    0.220888    0.102465    0.138144    11.00000    0.01552    0.01802 =
         0.01991   -0.00303    0.00627    0.00134
O1    7   -0.128908    0.428927    0.165291    11.00000    0.02586    0.03457 =
         0.03661    0.00338    0.01805    0.01036
O2    7   -0.089301    0.568458    0.091912    11.00000    0.03142    0.01936 =
         0.04220    0.00582    0.01611    0.00921
N1    6   -0.082122    0.465147    0.127150    11.00000    0.02357    0.02299 =
         0.02343   -0.00563    0.00910    0.00180
C1    1    0.305395    0.180709    0.255964    11.00000    0.01729    0.01341 =
         0.01505   -0.00380    0.00386    0.00172
C2    1    0.380395    0.236432    0.256785    11.00000    0.02219    0.02120 =
         0.01947    0.00265    0.00942    0.00152
AFIX  43
H2    2    0.393993    0.237319    0.207658    11.00000   -1.20000
AFIX   0
C3    1    0.435337    0.291583    0.334019    11.00000    0.01745    0.02029 =
         0.02687   -0.00063    0.00553   -0.00198
AFIX  43
H3    2    0.486872    0.328613    0.337153    11.00000   -1.20000
AFIX   0
C4    1    0.412486    0.290735    0.406048    11.00000    0.02662    0.01999 =
         0.02084   -0.00383    0.00256    0.00240
AFIX  43
H4    2    0.448693    0.328487    0.456983    11.00000   -1.20000
AFIX   0
C5    1    0.336460    0.234362    0.402906    11.00000    0.02538    0.02367 =
         0.01819   -0.00319    0.00908    0.00432
AFIX  43
H5    2    0.322131    0.235013    0.451598    11.00000   -1.20000
AFIX   0
C6    1    0.281170    0.176550    0.327124    11.00000    0.01566    0.02163 =
         0.02870    0.00282    0.00640    0.00377
AFIX  43
H6    2    0.230500    0.137100    0.324381    11.00000   -1.20000
AFIX   0
C7    1    0.117218    0.222646    0.129973    11.00000    0.01506    0.02218 =
         0.01702   -0.00357    0.00534    0.00405
C8    1    0.121175    0.349806    0.107837    11.00000    0.01679    0.02112 =
         0.02786    0.00299    0.00980    0.00205
AFIX  43
H8    2    0.167166    0.380274    0.094975    11.00000   -1.20000
AFIX   0
C9    1    0.054262    0.428500    0.105778    11.00000    0.02089    0.01845 =
         0.02639    0.00315    0.00779    0.00106
AFIX  43
H9    2    0.054253    0.513435    0.091096    11.00000   -1.20000
AFIX   0
C10   1   -0.012604    0.379215    0.125834    11.00000    0.01783    0.02245 =
         0.01770   -0.00364    0.00636    0.00080
C11   1   -0.017567    0.252847    0.146387    11.00000    0.01478    0.02398 =
         0.01907   -0.00150    0.00763   -0.00213
AFIX  43
H11   2   -0.064288    0.222696    0.158122    11.00000   -1.20000
AFIX   0
C12   1    0.049360    0.172495    0.148943    11.00000    0.01618    0.01815 =
         0.02183    0.00092    0.00573   -0.00025
AFIX  43
H12   2    0.048735    0.087393    0.162983    11.00000   -1.20000
AFIX   0
F1    4    0.403625    0.455500    0.033189    11.00000    0.02118    0.03690 =
         0.02554   -0.00282    0.01071    0.00031
F2    4    0.291900    0.573370    0.036802    11.00000    0.05485    0.04750 =
         0.03385    0.01302    0.02337    0.03111
F3    4    0.394899    0.504332    0.163528    11.00000    0.03943    0.02643 =
         0.01977   -0.00113    0.00947   -0.00669
F4    4    0.300250    0.365209    0.072695    11.00000    0.03902    0.03980 =
         0.02962   -0.00061    0.01088   -0.01989
B1    3    0.347452    0.474472    0.077458    11.00000    0.02422    0.02487 =
         0.01698    0.00300    0.00811    0.00227
HKLF    4
 
REM  owkm001                     New: C2/c
REM R1 =  0.0365 for   2415 Fo > 4sig(Fo)  and  0.0365 for all   2418 data
REM    190 parameters refined using      0 restraints
 
END
 
WGHT      0.0206     19.2810
REM Highest difference peak  0.602,  deepest hole -0.813,  1-sigma level  0.120
Q1    1   0.2924  0.1185  0.2009  11.00000  0.05    0.60
Q2    1   0.5000  0.3307  0.2500  10.50000  0.05    0.44
Q3    1  -0.1838  0.6102  0.0915  11.00000  0.05    0.44
Q4    1   0.2677 -0.0552  0.2363  11.00000  0.05    0.42
Q5    1   0.3987  0.4002  0.2642  11.00000  0.05    0.40
Q6    1   0.1396  0.1841  0.0996  11.00000  0.05    0.40
Q7    1   0.2275  0.4480  0.0302  11.00000  0.05    0.39
Q8    1   0.3979  0.6066  0.0697  11.00000  0.05    0.38
Q9    1   0.2191  0.2367  0.0909  11.00000  0.05    0.37
Q10   1   0.4220  0.1383  0.2867  11.00000  0.05    0.37
Q11   1   0.5100  0.3201  0.2999  11.00000  0.05    0.37
Q12   1   0.2751  0.3006 -0.0225  11.00000  0.05    0.37
Q13   1   0.0614  0.5029  0.0157  11.00000  0.05    0.36
Q14   1   0.1406  0.0958  0.0813  11.00000  0.05    0.35
Q15   1  -0.1726  0.4044  0.2503  11.00000  0.05    0.35
Q16   1   0.0950  0.2781  0.2353  11.00000  0.05    0.35
Q17   1  -0.1726  0.4021  0.0829  11.00000  0.05    0.35
Q18   1  -0.1884  0.6088  0.0427  11.00000  0.05    0.34
Q19   1   0.3115  0.2762  0.5111  11.00000  0.05    0.34
Q20   1   0.4662  0.2599  0.5129  11.00000  0.05    0.33
;
_database_code_depnum_ccdc_archive 'CCDC 990680'
