# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
# This journal is © The Owner Societies 2013


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 908910'
#TrackingRef 'TIE.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 I4'
_chemical_formula_weight         531.62
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'
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   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   14.979(3)
_cell_length_b                   4.3028(8)
_cell_length_c                   12.748(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.508(3)
_cell_angle_gamma                90.00
_cell_volume                     779.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2517
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      27.49
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    4.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    15.886
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.0950
_exptl_absorpt_correction_T_max  0.2319
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      110(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            3335
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.25
_reflns_number_total             1393
_reflns_number_gt                1344
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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^)+(0.0151P)^2^+20.3839P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1393
_refine_ls_number_parameters     58
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_restrained_S_all      1.243
_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
C1A C 0.4548(15) 0.525(5) 0.4960(18) 0.010(3) Uani 0.50 1 d PU . .
C1B C 0.4873(16) 0.447(5) 0.4564(18) 0.010(3) Uani 0.50 1 d PU . .
C2 C 0.0451(8) 0.980(3) 0.5293(9) 0.012(2) Uani 1 1 d U . .
I1 I 0.34409(5) 0.40431(19) 0.35217(6) 0.0182(2) Uani 1 1 d . . .
I2 I 0.41212(5) 0.73326(18) 0.62035(6) 0.0161(2) Uani 1 1 d . . .
I3 I 0.09242(5) 0.76950(17) 0.68480(6) 0.0150(2) Uani 1 1 d . . .
I4 I 0.15478(5) 1.13422(18) 0.47011(6) 0.0154(2) Uani 1 1 d . . .
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
C1A 0.007(4) 0.011(4) 0.011(4) 0.000(3) 0.003(3) 0.002(3)
C1B 0.007(4) 0.011(4) 0.011(4) 0.000(3) 0.003(3) 0.002(3)
C2 0.015(4) 0.012(4) 0.012(4) -0.001(3) 0.006(3) -0.004(3)
I1 0.0081(4) 0.0327(5) 0.0134(4) -0.0020(3) 0.0027(3) -0.0040(3)
I2 0.0152(4) 0.0216(4) 0.0146(4) 0.0000(3) 0.0091(3) 0.0060(3)
I3 0.0143(4) 0.0208(4) 0.0108(4) 0.0017(3) 0.0053(3) 0.0019(3)
I4 0.0109(4) 0.0216(4) 0.0170(4) -0.0011(3) 0.0092(3) -0.0026(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
C1A C1B 0.87(3) . ?
C1A C1B 0.90(3) 3_666 ?
C1A C1A 1.34(4) 3_666 ?
C1A I2 2.09(2) . ?
C1A I1 2.11(2) . ?
C1B C1A 0.90(3) 3_666 ?
C1B C1B 1.15(4) 3_666 ?
C1B I1 2.14(2) . ?
C1B I2 2.18(2) 3_666 ?
C2 C2 1.33(2) 3_576 ?
C2 I3 2.088(11) . ?
C2 I4 2.121(11) . ?
I2 C1B 2.18(2) 3_666 ?
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
C1B C1A C1B 81(3) . 3_666 ?
C1B C1A C1A 41(2) . 3_666 ?
C1B C1A C1A 40.0(19) 3_666 3_666 ?
C1B C1A I2 165(3) . . ?
C1B C1A I2 84(2) 3_666 . ?
C1A C1A I2 124(2) 3_666 . ?
C1B C1A I1 80(2) . . ?
C1B C1A I1 162(3) 3_666 . ?
C1A C1A I1 122(2) 3_666 . ?
I2 C1A I1 114.8(10) . . ?
C1A C1B C1A 99(3) . 3_666 ?
C1A C1B C1B 50(2) . 3_666 ?
C1A C1B C1B 49(2) 3_666 3_666 ?
C1A C1B I1 76(2) . . ?
C1A C1B I1 175(3) 3_666 . ?
C1B C1B I1 126(3) 3_666 . ?
C1A C1B I2 171(3) . 3_666 ?
C1A C1B I2 72(2) 3_666 3_666 ?
C1B C1B I2 121(3) 3_666 3_666 ?
I1 C1B I2 113.0(10) . 3_666 ?
C2 C2 I3 124.6(11) 3_576 . ?
C2 C2 I4 121.5(11) 3_576 . ?
I3 C2 I4 113.9(5) . . ?
C1A I1 C1B 23.7(7) . . ?
C1A I2 C1B 24.1(7) . 3_666 ?
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         2.205
_refine_diff_density_min         -2.121
_refine_diff_density_rms         0.324