# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 I O'
_chemical_formula_sum            'C12 H11 I O'
_chemical_formula_weight         298.11

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'
O O 0.0106 0.0060 '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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6246(16)
_cell_length_b                   8.867(3)
_cell_length_c                   9.748(3)
_cell_angle_alpha                107.355(7)
_cell_angle_beta                 91.179(5)
_cell_angle_gamma                95.669(7)
_cell_volume                     543.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1846
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.3

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    2.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.163
_exptl_absorpt_correction_T_max  0.328

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5185
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.34
_reflns_number_total             1964
_reflns_number_gt                1624
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_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 F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0476P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         1964
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.43166(4) 0.06916(3) 0.28167(3) 0.06463(16) Uani 1 1 d . . .
O1 O 1.0735(4) 0.2776(4) 0.5413(3) 0.0559(7) Uani 1 1 d . . .
C1 C 0.5401(6) 0.2675(5) 0.4524(4) 0.0505(10) Uani 1 1 d . . .
H1 H 0.4510 0.3420 0.4913 0.061 Uiso 1 1 calc R . .
C2 C 0.8934(6) 0.1882(5) 0.4655(4) 0.0512(10) Uani 1 1 d . . .
H2A H 0.8637 0.0913 0.4916 0.061 Uiso 1 1 calc R . .
H2B H 0.9084 0.1602 0.3624 0.061 Uiso 1 1 calc R . .
C3 C 0.7274(5) 0.2936(4) 0.5085(4) 0.0387(8) Uani 1 1 d . . .
C4 C 1.0166(5) 0.3896(5) 0.6686(4) 0.0447(9) Uani 1 1 d . . .
H4 H 1.1168 0.4838 0.6973 0.054 Uiso 1 1 calc R . .
C5 C 0.8070(6) 0.4354(5) 0.6351(4) 0.0458(9) Uani 1 1 d . . .
H5 H 0.8194 0.5340 0.6086 0.055 Uiso 1 1 calc R . .
C6 C 0.6881(6) 0.4525(5) 0.7714(5) 0.0565(11) Uani 1 1 d . . .
H6A H 0.6919 0.5632 0.8282 0.068 Uiso 1 1 calc R . .
H6B H 0.5476 0.4078 0.7474 0.068 Uiso 1 1 calc R . .
C7 C 0.7971(7) 0.3603(5) 0.8506(4) 0.0502(10) Uani 1 1 d . . .
C8 C 0.9816(6) 0.3239(4) 0.7921(4) 0.0442(9) Uani 1 1 d . . .
C9 C 1.1098(7) 0.2394(5) 0.8478(5) 0.0609(12) Uani 1 1 d . . .
H9 H 1.2336 0.2158 0.8082 0.073 Uiso 1 1 calc R . .
C10 C 1.0469(11) 0.1913(6) 0.9645(6) 0.0833(18) Uani 1 1 d . . .
H10 H 1.1287 0.1335 1.0036 0.100 Uiso 1 1 calc R . .
C11 C 0.8653(13) 0.2283(7) 1.0225(6) 0.091(2) Uani 1 1 d . . .
H11 H 0.8273 0.1958 1.1015 0.109 Uiso 1 1 calc R . .
C12 C 0.7372(9) 0.3117(6) 0.9684(5) 0.0734(15) Uani 1 1 d . . .
H12 H 0.6140 0.3350 1.0092 0.088 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 0.0495(2) 0.0700(3) 0.0627(2) 0.00523(16) -0.00566(14) -0.00103(15)
O1 0.0280(14) 0.082(2) 0.0567(17) 0.0192(15) 0.0066(12) 0.0062(13)
C1 0.038(2) 0.049(2) 0.062(2) 0.0116(19) -0.0013(18) 0.0091(17)
C2 0.035(2) 0.064(3) 0.051(2) 0.0115(19) 0.0038(17) 0.0087(19)
C3 0.0335(19) 0.042(2) 0.044(2) 0.0187(16) 0.0016(15) 0.0015(16)
C4 0.0314(19) 0.050(2) 0.052(2) 0.0165(18) -0.0016(16) -0.0041(16)
C5 0.039(2) 0.043(2) 0.056(2) 0.0177(18) 0.0003(17) 0.0030(17)
C6 0.042(2) 0.057(3) 0.061(3) 0.002(2) 0.0036(19) 0.007(2)
C7 0.058(3) 0.041(2) 0.039(2) -0.0027(16) 0.0029(17) -0.0081(18)
C8 0.043(2) 0.040(2) 0.045(2) 0.0100(16) -0.0078(16) -0.0062(17)
C9 0.064(3) 0.052(3) 0.064(3) 0.020(2) -0.021(2) -0.003(2)
C10 0.122(5) 0.053(3) 0.071(4) 0.025(3) -0.045(3) -0.013(3)
C11 0.144(7) 0.074(4) 0.048(3) 0.023(3) -0.011(3) -0.035(4)
C12 0.092(4) 0.066(3) 0.050(3) 0.006(2) 0.018(3) -0.019(3)

_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 C1 2.082(4) . ?
O1 C4 1.423(5) . ?
O1 C2 1.423(5) . ?
C1 C3 1.316(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.499(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C5 1.516(5) . ?
C4 C8 1.498(5) . ?
C4 C5 1.540(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.534(5) . ?
C5 H5 0.9800 . ?
C6 C7 1.502(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.386(6) . ?
C7 C12 1.394(6) . ?
C8 C9 1.388(6) . ?
C9 C10 1.387(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(9) . ?
C11 H11 0.9300 . ?
C12 H12 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
C4 O1 C2 108.1(3) . . ?
C3 C1 I1 123.8(3) . . ?
C3 C1 H1 118.1 . . ?
I1 C1 H1 118.1 . . ?
O1 C2 C3 105.9(3) . . ?
O1 C2 H2A 110.6 . . ?
C3 C2 H2A 110.6 . . ?
O1 C2 H2B 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C1 C3 C2 127.0(4) . . ?
C1 C3 C5 124.4(4) . . ?
C2 C3 C5 108.5(3) . . ?
O1 C4 C8 114.3(3) . . ?
O1 C4 C5 107.3(3) . . ?
C8 C4 C5 103.7(3) . . ?
O1 C4 H4 110.4 . . ?
C8 C4 H4 110.4 . . ?
C5 C4 H4 110.4 . . ?
C3 C5 C6 114.3(3) . . ?
C3 C5 C4 101.4(3) . . ?
C6 C5 C4 106.3(3) . . ?
C3 C5 H5 111.5 . . ?
C6 C5 H5 111.5 . . ?
C4 C5 H5 111.5 . . ?
C7 C6 C5 103.6(3) . . ?
C7 C6 H6A 111.0 . . ?
C5 C6 H6A 111.0 . . ?
C7 C6 H6B 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
C8 C7 C12 119.7(5) . . ?
C8 C7 C6 111.2(3) . . ?
C12 C7 C6 129.1(4) . . ?
C7 C8 C9 121.6(4) . . ?
C7 C8 C4 110.7(3) . . ?
C9 C8 C4 127.6(4) . . ?
C10 C9 C8 117.8(5) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 122.4(5) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C11 C12 C7 118.1(5) . . ?
C11 C12 H12 120.9 . . ?
C7 C12 H12 120.9 . . ?

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
C4 O1 C2 C3 26.3(4) . . . . ?
I1 C1 C3 C2 -1.7(6) . . . . ?
I1 C1 C3 C5 -178.4(3) . . . . ?
O1 C2 C3 C1 171.5(4) . . . . ?
O1 C2 C3 C5 -11.4(4) . . . . ?
C2 O1 C4 C8 83.3(4) . . . . ?
C2 O1 C4 C5 -31.2(4) . . . . ?
C1 C3 C5 C6 57.0(5) . . . . ?
C2 C3 C5 C6 -120.2(4) . . . . ?
C1 C3 C5 C4 170.9(4) . . . . ?
C2 C3 C5 C4 -6.4(4) . . . . ?
O1 C4 C5 C3 22.3(4) . . . . ?
C8 C4 C5 C3 -99.1(3) . . . . ?
O1 C4 C5 C6 142.0(3) . . . . ?
C8 C4 C5 C6 20.7(4) . . . . ?
C3 C5 C6 C7 90.7(4) . . . . ?
C4 C5 C6 C7 -20.2(4) . . . . ?
C5 C6 C7 C8 12.5(4) . . . . ?
C5 C6 C7 C12 -167.8(4) . . . . ?
C12 C7 C8 C9 0.1(6) . . . . ?
C6 C7 C8 C9 179.8(4) . . . . ?
C12 C7 C8 C4 -179.1(4) . . . . ?
C6 C7 C8 C4 0.7(4) . . . . ?
O1 C4 C8 C7 -130.0(3) . . . . ?
C5 C4 C8 C7 -13.5(4) . . . . ?
O1 C4 C8 C9 50.9(5) . . . . ?
C5 C4 C8 C9 167.4(4) . . . . ?
C7 C8 C9 C10 0.3(6) . . . . ?
C4 C8 C9 C10 179.3(4) . . . . ?
C8 C9 C10 C11 -0.7(7) . . . . ?
C9 C10 C11 C12 0.8(8) . . . . ?
C10 C11 C12 C7 -0.4(8) . . . . ?
C8 C7 C12 C11 0.0(6) . . . . ?
C6 C7 C12 C11 -179.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.095
_database_code_depnum_ccdc_archive 'CCDC 953992'