# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_c2c
_database_code_depnum_ccdc_archive 'CCDC 1044075'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 I O3'
_chemical_formula_weight         468.27

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           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                   26.291(14)
_cell_length_b                   8.781(5)
_cell_length_c                   18.363(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.863(4)
_cell_angle_gamma                90.00
_cell_volume                     3935(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5517
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      25.13

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856
_exptl_absorpt_coefficient_mu    1.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7031
_exptl_absorpt_correction_T_max  0.8795
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13931
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3666
_reflns_number_gt                2987
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0152P)²+3.7400P] 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     SHELXL
_refine_ls_extinction_coef       0.00444(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3666
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0529
_refine_ls_wR_factor_gt          0.0479
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.003
_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
C1 C 0.08427(11) -0.1591(3) 0.95481(16) 0.0449(6) Uani 1 1 d . . .
H1 H 0.0863 -0.1522 1.0063 0.054 Uiso 1 1 calc R . .
C2 C 0.09717(12) -0.2935(3) 0.92771(19) 0.0542(7) Uani 1 1 d . . .
H2 H 0.1077 -0.3774 0.9609 0.065 Uiso 1 1 calc R . .
C3 C 0.09460(13) -0.3048(4) 0.8525(2) 0.0631(9) Uani 1 1 d . . .
H3 H 0.1041 -0.3955 0.8347 0.076 Uiso 1 1 calc R . .
C4 C 0.07808(14) -0.1829(4) 0.80326(18) 0.0675(9) Uani 1 1 d . . .
H4 H 0.0760 -0.1912 0.7517 0.081 Uiso 1 1 calc R . .
C5 C 0.06440(11) -0.0477(3) 0.82922(15) 0.0509(7) Uani 1 1 d . . .
H5 H 0.0525 0.0345 0.7951 0.061 Uiso 1 1 calc R . .
C6 C 0.06840(10) -0.0343(3) 0.90617(14) 0.0362(6) Uani 1 1 d . . .
C7 C 0.05548(10) 0.1126(3) 0.93493(14) 0.0363(6) Uani 1 1 d . . .
C8 C 0.09032(11) 0.1743(3) 1.00151(14) 0.0380(6) Uani 1 1 d . . .
C9 C 0.14702(11) 0.1202(3) 1.04754(15) 0.0410(6) Uani 1 1 d . . .
C10 C 0.18369(10) 0.0814(3) 1.00519(14) 0.0384(6) Uani 1 1 d . . .
C11 C 0.17991(11) 0.1579(3) 0.93755(16) 0.0478(7) Uani 1 1 d . . .
H11 H 0.1517 0.2273 0.9153 0.057 Uiso 1 1 calc R . .
C12 C 0.21722(13) 0.1329(4) 0.90262(18) 0.0581(8) Uani 1 1 d . . .
H12 H 0.2144 0.1858 0.8574 0.070 Uiso 1 1 calc R . .
C13 C 0.25869(13) 0.0293(4) 0.93489(18) 0.0585(8) Uani 1 1 d . . .
H13 H 0.2837 0.0108 0.9111 0.070 Uiso 1 1 calc R . .
C14 C 0.26316(12) -0.0463(3) 1.00186(17) 0.0525(7) Uani 1 1 d . . .
H14 H 0.2914 -0.1159 1.0235 0.063 Uiso 1 1 calc R . .
C15 C 0.22645(11) -0.0211(3) 1.03793(15) 0.0427(6) Uani 1 1 d . . .
C16 C 0.23178(13) -0.1130(3) 1.10928(18) 0.0529(8) Uani 1 1 d . . .
C17 C 0.28986(18) -0.1854(6) 1.2348(2) 0.1287(19) Uani 1 1 d . . .
H17A H 0.2571 -0.1898 1.2464 0.193 Uiso 1 1 calc R . .
H17B H 0.3191 -0.1422 1.2787 0.193 Uiso 1 1 calc R . .
H17C H 0.2998 -0.2863 1.2250 0.193 Uiso 1 1 calc R . .
C18 C 0.00268(11) 0.1826(3) 0.88646(14) 0.0388(6) Uani 1 1 d . . .
C19 C 0.00095(13) 0.3268(3) 0.85585(16) 0.0544(8) Uani 1 1 d . . .
H19 H 0.0332 0.3819 0.8674 0.065 Uiso 1 1 calc R . .
C20 C -0.04818(16) 0.3901(4) 0.80828(18) 0.0689(10) Uani 1 1 d . . .
H20 H -0.0488 0.4866 0.7871 0.083 Uiso 1 1 calc R . .
C21 C -0.09539(16) 0.3124(5) 0.79234(19) 0.0745(11) Uani 1 1 d . . .
H21 H -0.1285 0.3566 0.7612 0.089 Uiso 1 1 calc R . .
C22 C -0.09488(13) 0.1689(4) 0.82160(19) 0.0685(10) Uani 1 1 d . . .
H22 H -0.1275 0.1160 0.8105 0.082 Uiso 1 1 calc R . .
C23 C -0.04577(12) 0.1030(3) 0.86762(16) 0.0503(7) Uani 1 1 d . . .
H23 H -0.0453 0.0041 0.8861 0.060 Uiso 1 1 calc R . .
I1 I 0.067918(8) 0.35633(2) 1.057444(11) 0.05418(10) Uani 1 1 d . . .
O1 O 0.16416(9) 0.1167(2) 1.11829(11) 0.0644(6) Uani 1 1 d . . .
O2 O 0.19845(10) -0.1991(3) 1.11367(13) 0.0709(6) Uani 1 1 d . . .
O3 O 0.27996(9) -0.0899(3) 1.16478(13) 0.0894(8) 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
C1 C2 1.372(4) . ?
C1 C6 1.377(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.480(3) . ?
C7 C8 1.339(3) . ?
C7 C18 1.475(4) . ?
C8 C9 1.491(4) . ?
C8 I1 2.099(2) . ?
C9 O1 1.206(3) . ?
C9 C10 1.486(4) . ?
C10 C11 1.382(4) . ?
C10 C15 1.390(3) . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.500(4) . ?
C16 O2 1.183(4) . ?
C16 O3 1.312(4) . ?
C17 O3 1.476(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.379(4) . ?
C18 C19 1.380(4) . ?
C19 C20 1.378(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.350(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(4) . ?
C22 H22 0.9300 . ?
C23 H23 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
C2 C1 C6 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 C7 121.1(2) . . ?
C5 C6 C7 119.9(2) . . ?
C8 C7 C18 123.5(2) . . ?
C8 C7 C6 120.6(2) . . ?
C18 C7 C6 115.9(2) . . ?
C7 C8 C9 126.0(2) . . ?
C7 C8 I1 122.26(19) . . ?
C9 C8 I1 111.64(16) . . ?
O1 C9 C10 120.2(2) . . ?
O1 C9 C8 120.8(2) . . ?
C10 C9 C8 118.9(2) . . ?
C11 C10 C15 118.6(2) . . ?
C11 C10 C9 121.0(2) . . ?
C15 C10 C9 120.0(2) . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C10 119.7(3) . . ?
C14 C15 C16 118.7(2) . . ?
C10 C15 C16 121.6(2) . . ?
O2 C16 O3 124.8(3) . . ?
O2 C16 C15 124.9(3) . . ?
O3 C16 C15 110.2(3) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 118.4(3) . . ?
C23 C18 C7 120.9(2) . . ?
C19 C18 C7 120.6(3) . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.5(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 119.8(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 120.5(3) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C16 O3 C17 113.3(3) . . ?

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
C6 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 -1.3(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
C2 C1 C6 C7 -178.7(2) . . . . ?
C4 C5 C6 C1 -2.2(4) . . . . ?
C4 C5 C6 C7 178.0(3) . . . . ?
C1 C6 C7 C8 50.2(4) . . . . ?
C5 C6 C7 C8 -130.0(3) . . . . ?
C1 C6 C7 C18 -129.2(3) . . . . ?
C5 C6 C7 C18 50.5(3) . . . . ?
C18 C7 C8 C9 -171.7(2) . . . . ?
C6 C7 C8 C9 8.8(4) . . . . ?
C18 C7 C8 I1 12.3(4) . . . . ?
C6 C7 C8 I1 -167.15(17) . . . . ?
C7 C8 C9 O1 -139.2(3) . . . . ?
I1 C8 C9 O1 37.2(3) . . . . ?
C7 C8 C9 C10 45.4(4) . . . . ?
I1 C8 C9 C10 -138.24(19) . . . . ?
O1 C9 C10 C11 -143.3(3) . . . . ?
C8 C9 C10 C11 32.2(3) . . . . ?
O1 C9 C10 C15 29.6(4) . . . . ?
C8 C9 C10 C15 -154.9(2) . . . . ?
C15 C10 C11 C12 0.5(4) . . . . ?
C9 C10 C11 C12 173.5(2) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C14 -1.0(5) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C13 C14 C15 C10 0.9(4) . . . . ?
C13 C14 C15 C16 177.1(3) . . . . ?
C11 C10 C15 C14 -1.2(4) . . . . ?
C9 C10 C15 C14 -174.3(2) . . . . ?
C11 C10 C15 C16 -177.4(3) . . . . ?
C9 C10 C15 C16 9.6(4) . . . . ?
C14 C15 C16 O2 -116.9(3) . . . . ?
C10 C15 C16 O2 59.3(4) . . . . ?
C14 C15 C16 O3 59.9(3) . . . . ?
C10 C15 C16 O3 -123.9(3) . . . . ?
C8 C7 C18 C23 -124.4(3) . . . . ?
C6 C7 C18 C23 55.0(3) . . . . ?
C8 C7 C18 C19 58.6(4) . . . . ?
C6 C7 C18 C19 -121.9(3) . . . . ?
C23 C18 C19 C20 0.7(4) . . . . ?
C7 C18 C19 C20 177.7(3) . . . . ?
C18 C19 C20 C21 1.3(5) . . . . ?
C19 C20 C21 C22 -1.5(5) . . . . ?
C20 C21 C22 C23 -0.1(5) . . . . ?
C19 C18 C23 C22 -2.4(4) . . . . ?
C7 C18 C23 C22 -179.4(2) . . . . ?
C21 C22 C23 C18 2.1(4) . . . . ?
O2 C16 O3 C17 1.1(5) . . . . ?
C15 C16 O3 C17 -175.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.053
