# Electronic Supplementary Material (ESI) for Chemical Science
# 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
#  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_global


data_anc1
#TrackingRef 'Compound 1.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 I2 O2'
_chemical_formula_sum            'C18 H18 I2 O2'
_chemical_formula_weight         520.12
_chemical_absolute_configuration ad

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.7537(2)
_cell_length_b                   8.7833(3)
_cell_length_c                   28.0793(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1912.29(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    3.293
_exptl_absorpt_correction_type   Multi-scan?
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_T_max  0.9477
_exptl_absorpt_process_details   
;
SADABS program multi-scan
Blessing, Acta Cryst. (1995) A51 33-38
;

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20538
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.08
_reflns_number_total             3395
_reflns_number_gt                3225
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2 V.1.0-27(Bruker 2005)'
_computing_cell_refinement       'SAINT V7.12A (Bruker 2004)'
_computing_data_reduction        'SAINT and XPREP Version 6.14, 2003'
_computing_structure_solution    'SHELXS-97 in SHELXTL ver. 6.12, 2001'
_computing_structure_refinement  'SHELXL-97 in SHELXTL ver. 6.12, 2001'
_computing_molecular_graphics    'Bruker SHELXTL suite ver. 6.12, 2001'
_computing_publication_material  'Bruker SHELXTL suite ver. 6.12, 2001'

_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^)+(0.0350P)^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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(4)
_refine_ls_number_reflns         3395
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0485
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_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 1.18180(4) 0.39626(4) 0.193804(12) 0.02147(10) Uani 1 1 d . . .
I2 I 0.63150(4) 0.66412(4) 0.148913(13) 0.02383(10) Uani 1 1 d . . .
O1 O 0.4554(5) 0.1679(5) 0.22003(13) 0.0205(8) Uani 1 1 d . . .
H1A H 0.429(7) 0.088(6) 0.2363(18) 0.013(14) Uiso 1 1 d . . .
O2 O 0.6423(5) 0.4094(4) 0.23688(11) 0.0199(8) Uani 1 1 d . . .
H2A H 0.5648 0.3469 0.2403 0.030 Uiso 1 1 calc R . .
C1 C 0.8210(7) 0.5113(6) 0.17618(17) 0.0177(11) Uani 1 1 d . . .
C2 C 0.9854(7) 0.5480(6) 0.17105(18) 0.0172(11) Uani 1 1 d . . .
C3 C 1.0576(7) 0.6887(6) 0.14916(19) 0.0189(11) Uani 1 1 d . . .
C4 C 1.1342(8) 0.6828(7) 0.1046(2) 0.0339(15) Uani 1 1 d . . .
H4A H 1.1377 0.5913 0.0879 0.041 Uiso 1 1 calc R . .
C5 C 1.2059(9) 0.8137(8) 0.0848(2) 0.0439(18) Uani 1 1 d . . .
H5A H 1.2540 0.8101 0.0544 0.053 Uiso 1 1 calc R . .
C6 C 1.2060(9) 0.9464(8) 0.1095(2) 0.0392(17) Uani 1 1 d . . .
H6A H 1.2537 1.0335 0.0960 0.047 Uiso 1 1 calc R . .
C7 C 1.1341(8) 0.9525(7) 0.1553(2) 0.0330(14) Uani 1 1 d . . .
H7A H 1.1356 1.0430 0.1725 0.040 Uiso 1 1 calc R . .
C8 C 1.0610(8) 0.8231(6) 0.1749(2) 0.0253(12) Uani 1 1 d . . .
H8A H 1.0141 0.8265 0.2053 0.030 Uiso 1 1 calc R . .
C9 C 0.7463(6) 0.3671(6) 0.19734(17) 0.0158(11) Uani 1 1 d . . .
H9A H 0.8424 0.3057 0.2094 0.019 Uiso 1 1 calc R . .
C10 C 0.6476(6) 0.2706(6) 0.16129(16) 0.0161(11) Uani 1 1 d . . .
H10A H 0.5486 0.3300 0.1501 0.019 Uiso 1 1 calc R . .
C11 C 0.5793(6) 0.1259(6) 0.18467(18) 0.0204(12) Uani 1 1 d . . .
H11A H 0.5259 0.0610 0.1609 0.024 Uiso 1 1 calc R . .
H11B H 0.6734 0.0701 0.1993 0.024 Uiso 1 1 calc R . .
C12 C 0.7589(7) 0.2293(6) 0.11780(18) 0.0204(12) Uani 1 1 d . . .
H12A H 0.8192 0.3197 0.1071 0.025 Uiso 1 1 calc R . .
H12B H 0.8448 0.1551 0.1273 0.025 Uiso 1 1 calc R . .
C13 C 0.6552(7) 0.1652(6) 0.07683(16) 0.0213(11) Uani 1 1 d . . .
C14 C 0.6835(9) 0.0179(7) 0.06008(19) 0.0288(13) Uani 1 1 d . . .
H14A H 0.7669 -0.0434 0.0742 0.035 Uiso 1 1 calc R . .
C15 C 0.5318(8) 0.2527(8) 0.0542(2) 0.0287(14) Uani 1 1 d . . .
H15A H 0.5138 0.3519 0.0646 0.034 Uiso 1 1 calc R . .
C16 C 0.4354(9) 0.1993(9) 0.0171(2) 0.0408(18) Uani 1 1 d . . .
H16A H 0.3521 0.2604 0.0028 0.049 Uiso 1 1 calc R . .
C17 C 0.4638(9) 0.0535(9) 0.0012(2) 0.0421(19) Uani 1 1 d . . .
H17A H 0.3992 0.0155 -0.0240 0.051 Uiso 1 1 calc R . .
C20 C 0.5867(10) -0.0367(8) 0.0223(2) 0.0423(18) Uani 1 1 d . . .
H20A H 0.6051 -0.1350 0.0111 0.051 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 0.01243(16) 0.02214(18) 0.02984(18) 0.00111(15) 0.00128(14) 0.00037(14)
I2 0.01790(18) 0.01854(18) 0.0350(2) 0.00759(16) -0.00160(15) 0.00088(15)
O1 0.0195(19) 0.0180(19) 0.0241(19) 0.0045(18) 0.0089(15) -0.0005(18)
O2 0.0197(19) 0.0181(18) 0.0219(17) -0.0012(15) 0.0065(15) -0.0021(17)
C1 0.020(3) 0.014(2) 0.020(2) -0.001(2) -0.002(2) 0.002(2)
C2 0.019(3) 0.014(3) 0.018(3) 0.000(2) 0.000(2) 0.001(2)
C3 0.017(3) 0.020(3) 0.019(3) 0.002(2) -0.006(2) -0.005(2)
C4 0.037(4) 0.036(3) 0.028(3) 0.000(3) 0.006(3) -0.018(3)
C5 0.047(4) 0.052(4) 0.033(3) 0.003(3) 0.003(3) -0.024(4)
C6 0.029(4) 0.040(4) 0.048(4) 0.024(3) -0.013(3) -0.021(3)
C7 0.036(3) 0.021(3) 0.042(4) 0.003(3) -0.013(3) -0.007(3)
C8 0.029(3) 0.022(3) 0.025(3) 0.003(3) -0.002(2) -0.005(3)
C9 0.011(2) 0.016(3) 0.020(2) -0.002(2) 0.000(2) 0.0028(19)
C10 0.010(3) 0.020(3) 0.018(2) 0.006(2) 0.001(2) 0.001(2)
C11 0.016(3) 0.022(3) 0.024(3) -0.001(2) 0.004(2) 0.000(2)
C12 0.019(3) 0.020(3) 0.023(3) -0.002(2) 0.003(2) 0.002(2)
C13 0.026(3) 0.025(3) 0.012(2) 0.003(2) 0.005(2) -0.006(3)
C14 0.038(3) 0.024(3) 0.024(3) 0.000(2) 0.007(3) -0.004(3)
C15 0.025(3) 0.037(4) 0.024(3) 0.009(3) -0.001(3) -0.001(3)
C16 0.034(4) 0.065(5) 0.024(3) 0.010(3) -0.006(3) -0.003(4)
C17 0.043(4) 0.064(5) 0.019(3) 0.000(3) -0.006(3) -0.021(4)
C20 0.057(5) 0.045(4) 0.025(3) -0.009(3) 0.014(3) -0.017(4)

_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 C2 2.122(5) . ?
I2 C1 2.133(5) . ?
O1 C11 1.430(6) . ?
O1 H1A 0.86(5) . ?
O2 C9 1.422(6) . ?
O2 H2A 0.8200 . ?
C1 C2 1.323(8) . ?
C1 C9 1.514(7) . ?
C2 C3 1.490(7) . ?
C3 C8 1.384(8) . ?
C3 C4 1.387(8) . ?
C4 C5 1.394(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.356(10) . ?
C5 H5A 0.9300 . ?
C6 C7 1.404(9) . ?
C6 H6A 0.9300 . ?
C7 C8 1.383(8) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 C10 1.526(7) . ?
C9 H9A 0.9800 . ?
C10 C11 1.526(7) . ?
C10 C12 1.538(7) . ?
C10 H10A 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.512(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.382(8) . ?
C13 C14 1.394(8) . ?
C14 C20 1.385(9) . ?
C14 H14A 0.9300 . ?
C15 C16 1.366(9) . ?
C15 H15A 0.9300 . ?
C16 C17 1.374(11) . ?
C16 H16A 0.9300 . ?
C17 C20 1.373(10) . ?
C17 H17A 0.9300 . ?
C20 H20A 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
C11 O1 H1A 108(3) . . ?
C9 O2 H2A 109.5 . . ?
C2 C1 C9 128.0(5) . . ?
C2 C1 I2 118.1(4) . . ?
C9 C1 I2 113.8(4) . . ?
C1 C2 C3 127.6(5) . . ?
C1 C2 I1 120.4(4) . . ?
C3 C2 I1 112.1(4) . . ?
C8 C3 C4 119.7(5) . . ?
C8 C3 C2 120.0(5) . . ?
C4 C3 C2 120.1(5) . . ?
C3 C4 C5 120.0(6) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 120.3(6) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 120.1(6) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
C8 C7 C6 119.7(6) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C7 C8 C3 120.1(5) . . ?
C7 C8 H8A 120.0 . . ?
C3 C8 H8A 120.0 . . ?
O2 C9 C1 107.7(4) . . ?
O2 C9 C10 112.3(4) . . ?
C1 C9 C10 113.3(4) . . ?
O2 C9 H9A 107.8 . . ?
C1 C9 H9A 107.8 . . ?
C10 C9 H9A 107.8 . . ?
C9 C10 C11 110.6(4) . . ?
C9 C10 C12 112.1(4) . . ?
C11 C10 C12 109.9(4) . . ?
C9 C10 H10A 108.1 . . ?
C11 C10 H10A 108.1 . . ?
C12 C10 H10A 108.1 . . ?
O1 C11 C10 108.5(4) . . ?
O1 C11 H11A 110.0 . . ?
C10 C11 H11A 110.0 . . ?
O1 C11 H11B 110.0 . . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C13 C12 C10 113.2(4) . . ?
C13 C12 H12A 108.9 . . ?
C10 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C10 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C15 C13 C14 118.0(5) . . ?
C15 C13 C12 120.7(5) . . ?
C14 C13 C12 121.2(5) . . ?
C20 C14 C13 119.6(6) . . ?
C20 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C16 C15 C13 122.6(6) . . ?
C16 C15 H15A 118.7 . . ?
C13 C15 H15A 118.7 . . ?
C15 C16 C17 118.6(7) . . ?
C15 C16 H16A 120.7 . . ?
C17 C16 H16A 120.7 . . ?
C20 C17 C16 120.6(6) . . ?
C20 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C17 C20 C14 120.4(6) . . ?
C17 C20 H20A 119.8 . . ?
C14 C20 H20A 119.8 . . ?

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
C9 C1 C2 C3 178.5(5) . . . . ?
I2 C1 C2 C3 1.9(7) . . . . ?
C9 C1 C2 I1 0.0(8) . . . . ?
I2 C1 C2 I1 -176.6(2) . . . . ?
C1 C2 C3 C8 78.7(7) . . . . ?
I1 C2 C3 C8 -102.8(5) . . . . ?
C1 C2 C3 C4 -106.6(7) . . . . ?
I1 C2 C3 C4 72.0(6) . . . . ?
C8 C3 C4 C5 -3.4(9) . . . . ?
C2 C3 C4 C5 -178.2(6) . . . . ?
C3 C4 C5 C6 2.0(11) . . . . ?
C4 C5 C6 C7 0.2(11) . . . . ?
C5 C6 C7 C8 -0.9(10) . . . . ?
C6 C7 C8 C3 -0.5(9) . . . . ?
C4 C3 C8 C7 2.7(9) . . . . ?
C2 C3 C8 C7 177.5(5) . . . . ?
C2 C1 C9 O2 120.4(6) . . . . ?
I2 C1 C9 O2 -62.8(4) . . . . ?
C2 C1 C9 C10 -114.7(6) . . . . ?
I2 C1 C9 C10 62.0(5) . . . . ?
O2 C9 C10 C11 -58.8(5) . . . . ?
C1 C9 C10 C11 178.8(4) . . . . ?
O2 C9 C10 C12 178.2(4) . . . . ?
C1 C9 C10 C12 55.8(6) . . . . ?
C9 C10 C11 O1 64.8(5) . . . . ?
C12 C10 C11 O1 -171.0(4) . . . . ?
C9 C10 C12 C13 -167.0(4) . . . . ?
C11 C10 C12 C13 69.6(6) . . . . ?
C10 C12 C13 C15 63.3(6) . . . . ?
C10 C12 C13 C14 -118.1(5) . . . . ?
C15 C13 C14 C20 -1.0(8) . . . . ?
C12 C13 C14 C20 -179.6(5) . . . . ?
C14 C13 C15 C16 1.4(9) . . . . ?
C12 C13 C15 C16 180.0(5) . . . . ?
C13 C15 C16 C17 -0.9(10) . . . . ?
C15 C16 C17 C20 0.0(10) . . . . ?
C16 C17 C20 C14 0.3(10) . . . . ?
C13 C14 C20 C17 0.2(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.86(5) 1.82(6) 2.682(5) 172(5) 3_645
O1 H1A I2 0.86(5) 3.32(5) 3.741(4) 113(4) 3_645
O2 H2A O1 0.82 1.88 2.613(5) 149.0 .
O2 H2A I1 0.82 3.27 3.772(4) 121.9 1_455

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.248


_database_code_depnum_ccdc_archive 'CCDC 930356'