# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
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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_111219b_0m
_database_code_depnum_ccdc_archive 'CCDC 908909'
#TrackingRef 'TIE-I.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H36 I5 N'
_chemical_formula_weight         900.98
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'
N N 0.0061 0.0033 '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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   9.003(3)
_cell_length_b                   9.062(3)
_cell_length_c                   19.036(7)
_cell_angle_alpha                81.642(6)
_cell_angle_beta                 80.716(6)
_cell_angle_gamma                64.652(6)
_cell_volume                     1380.0(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2417
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.80
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    5.638
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3839
_exptl_absorpt_correction_T_max  0.4851
_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            6588
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.1043
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4768
_reflns_number_gt                3633
_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^)+(0.1589P)^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         4768
_refine_ls_number_parameters     222
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.2441
_refine_ls_wR_factor_gt          0.2239
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.019
_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
C1 C 0.5012(14) 0.1408(16) 0.2582(8) 0.052(3) Uani 1 1 d . . .
H1A H 0.4212 0.2470 0.2758 0.063 Uiso 1 1 calc R . .
H1B H 0.5425 0.1634 0.2082 0.063 Uiso 1 1 calc R . .
C2 C 0.6450(16) 0.0718(18) 0.3022(9) 0.064(4) Uani 1 1 d . . .
H2A H 0.7209 -0.0395 0.2886 0.077 Uiso 1 1 calc R . .
H2B H 0.6039 0.0628 0.3534 0.077 Uiso 1 1 calc R . .
C3 C 0.739(2) 0.181(2) 0.2907(11) 0.087(5) Uani 1 1 d . . .
H3A H 0.7786 0.1914 0.2393 0.104 Uiso 1 1 calc R . .
H3B H 0.6628 0.2924 0.3045 0.104 Uiso 1 1 calc R . .
C4 C 0.880(2) 0.118(3) 0.3319(14) 0.120(8) Uani 1 1 d . . .
H4A H 0.9427 0.0003 0.3273 0.181 Uiso 1 1 calc R . .
H4B H 0.8412 0.1368 0.3823 0.181 Uiso 1 1 calc R . .
H4C H 0.9523 0.1747 0.3138 0.181 Uiso 1 1 calc R . .
C5 C 0.3579(15) -0.0194(15) 0.3318(7) 0.051(3) Uani 1 1 d . . .
H5A H 0.4572 -0.0998 0.3538 0.061 Uiso 1 1 calc R . .
H5B H 0.2882 -0.0771 0.3278 0.061 Uiso 1 1 calc R . .
C6 C 0.2614(17) 0.1162(16) 0.3819(7) 0.054(3) Uani 1 1 d . . .
H6A H 0.1552 0.1909 0.3635 0.065 Uiso 1 1 calc R . .
H6B H 0.3256 0.1808 0.3837 0.065 Uiso 1 1 calc R . .
C7 C 0.228(2) 0.042(2) 0.4571(8) 0.084(5) Uani 1 1 d . . .
H7A H 0.1654 -0.0244 0.4555 0.101 Uiso 1 1 calc R . .
H7B H 0.3341 -0.0307 0.4763 0.101 Uiso 1 1 calc R . .
C8 C 0.135(4) 0.171(4) 0.5019(14) 0.183(16) Uani 1 1 d . . .
H8A H 0.2030 0.2288 0.5075 0.274 Uiso 1 1 calc R . .
H8B H 0.1032 0.1264 0.5488 0.274 Uiso 1 1 calc R . .
H8C H 0.0359 0.2485 0.4802 0.274 Uiso 1 1 calc R . .
C9 C 0.5321(14) -0.1172(14) 0.2195(7) 0.046(3) Uani 1 1 d . . .
H9A H 0.5815 -0.0814 0.1737 0.055 Uiso 1 1 calc R . .
H9B H 0.6230 -0.1840 0.2492 0.055 Uiso 1 1 calc R . .
C10 C 0.4504(18) -0.2234(18) 0.2045(8) 0.062(3) Uani 1 1 d . . .
H10A H 0.3631 -0.1613 0.1726 0.074 Uiso 1 1 calc R . .
H10B H 0.3998 -0.2608 0.2496 0.074 Uiso 1 1 calc R . .
C11 C 0.590(2) -0.372(2) 0.1680(10) 0.081(5) Uani 1 1 d . . .
H11A H 0.6425 -0.3338 0.1240 0.097 Uiso 1 1 calc R . .
H11B H 0.6751 -0.4353 0.2006 0.097 Uiso 1 1 calc R . .
C12 C 0.514(3) -0.479(2) 0.1501(11) 0.098(6) Uani 1 1 d . . .
H12A H 0.3949 -0.4312 0.1661 0.147 Uiso 1 1 calc R . .
H12B H 0.5659 -0.5886 0.1742 0.147 Uiso 1 1 calc R . .
H12C H 0.5307 -0.4857 0.0983 0.147 Uiso 1 1 calc R . .
C13 C 0.2594(14) 0.1357(16) 0.2201(7) 0.051(3) Uani 1 1 d U . .
H13A H 0.1963 0.0684 0.2218 0.061 Uiso 1 1 calc R . .
H13B H 0.1885 0.2329 0.2465 0.061 Uiso 1 1 calc R . .
C14 C 0.2925(19) 0.193(2) 0.1435(9) 0.073(4) Uani 1 1 d U . .
H14A H 0.3685 0.0978 0.1168 0.088 Uiso 1 1 calc R . .
H14B H 0.3466 0.2688 0.1411 0.088 Uiso 1 1 calc R . .
C17 C 0.5062(15) 0.5157(15) 0.4653(7) 0.050(3) Uani 1 1 d . . .
C18 C 0.950(2) 0.990(2) 0.0238(8) 0.080(5) Uani 1 1 d . . .
I1 I 0.71112(10) 0.54618(10) 0.40390(4) 0.0513(3) Uani 1 1 d . . .
I2 I 0.32060(10) 0.54425(10) 0.40185(4) 0.0496(3) Uani 1 1 d . . .
I3 I 0.99710(12) 0.83646(12) 0.12174(5) 0.0625(3) Uani 1 1 d . . .
I4 I 0.69196(13) 1.13214(17) 0.01892(6) 0.0868(4) Uani 1 1 d . . .
I5 I 0.03662(10) 0.59870(11) 0.28029(5) 0.0543(3) Uani 1 1 d . . .
N1 N 0.4118(11) 0.0365(11) 0.2583(5) 0.044(2) Uani 1 1 d . . .
C15 C 0.130(3) 0.281(3) 0.1092(11) 0.111(6) Uani 1 1 d U . .
H15A H 0.0745 0.2062 0.1120 0.133 Uiso 1 1 calc R . .
H15B H 0.0546 0.3780 0.1348 0.133 Uiso 1 1 calc R . .
C16 C 0.170(3) 0.333(4) 0.0316(14) 0.143(8) Uani 1 1 d U . .
H16A H 0.2058 0.4222 0.0293 0.214 Uiso 1 1 calc R . .
H16B H 0.0719 0.3713 0.0065 0.214 Uiso 1 1 calc R . .
H16C H 0.2596 0.2398 0.0088 0.214 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
C1 0.033(6) 0.044(7) 0.082(9) -0.013(6) -0.004(6) -0.016(5)
C2 0.050(8) 0.054(8) 0.095(11) -0.007(8) -0.008(7) -0.027(7)
C3 0.063(10) 0.085(12) 0.130(16) -0.026(11) -0.013(10) -0.041(9)
C4 0.077(13) 0.15(2) 0.17(2) -0.007(17) -0.044(14) -0.074(14)
C5 0.042(6) 0.041(7) 0.071(9) -0.012(6) 0.000(6) -0.020(5)
C6 0.060(8) 0.052(8) 0.046(7) -0.007(6) 0.003(6) -0.021(6)
C7 0.102(13) 0.083(12) 0.059(9) -0.029(8) 0.024(9) -0.034(10)
C8 0.19(3) 0.14(3) 0.11(2) -0.010(18) 0.055(19) 0.01(2)
C9 0.046(6) 0.038(6) 0.053(7) -0.010(5) 0.005(5) -0.020(5)
C10 0.072(9) 0.053(8) 0.065(9) -0.016(7) -0.001(7) -0.030(7)
C11 0.101(13) 0.054(9) 0.091(12) -0.013(8) -0.015(10) -0.032(9)
C12 0.128(17) 0.076(12) 0.093(13) -0.013(10) -0.052(12) -0.028(11)
C13 0.041(6) 0.055(7) 0.059(6) -0.020(5) 0.000(5) -0.021(5)
C14 0.064(8) 0.065(9) 0.083(8) 0.009(7) 0.000(6) -0.026(7)
C17 0.052(7) 0.043(7) 0.058(7) -0.011(6) -0.005(6) -0.022(6)
C18 0.104(13) 0.085(12) 0.061(10) -0.005(9) -0.004(8) -0.050(10)
I1 0.0518(5) 0.0533(6) 0.0502(5) -0.0005(4) -0.0067(4) -0.0241(4)
I2 0.0551(5) 0.0499(5) 0.0489(5) -0.0031(4) -0.0117(4) -0.0249(4)
I3 0.0775(7) 0.0662(6) 0.0459(5) 0.0036(4) -0.0115(4) -0.0327(5)
I4 0.0537(6) 0.1055(10) 0.0705(7) 0.0114(6) -0.0021(5) -0.0113(6)
I5 0.0496(5) 0.0512(5) 0.0541(5) 0.0037(4) -0.0111(4) -0.0141(4)
N1 0.037(5) 0.036(5) 0.057(6) -0.005(4) 0.001(4) -0.015(4)
C15 0.108(9) 0.109(10) 0.101(8) -0.010(7) -0.038(7) -0.021(7)
C16 0.150(11) 0.142(12) 0.124(9) 0.001(8) -0.037(8) -0.045(8)
_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 N1 1.481(15) . ?
C1 C2 1.507(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.535(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.46(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N1 1.496(16) . ?
C5 C6 1.527(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.53(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.42(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.517(18) . ?
C9 N1 1.552(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.55(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.50(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.50(2) . ?
C13 N1 1.514(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.54(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C17 C17 1.31(2) 2_666 ?
C17 I1 2.119(12) . ?
C17 I2 2.122(13) . ?
C18 C18 1.22(3) 2_775 ?
C18 I4 2.13(2) . ?
C18 I3 2.143(17) . ?
C15 C16 1.52(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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
N1 C1 C2 116.1(11) . . ?
N1 C1 H1A 108.3 . . ?
C2 C1 H1A 108.3 . . ?
N1 C1 H1B 108.3 . . ?
C2 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 C3 111.0(13) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 112.7(17) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 115.3(10) . . ?
N1 C5 H5A 108.5 . . ?
C6 C5 H5A 108.5 . . ?
N1 C5 H5B 108.5 . . ?
C6 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 C7 110.1(12) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C6 108.6(18) . . ?
C8 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 113.7(10) . . ?
C10 C9 H9A 108.8 . . ?
N1 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
N1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 106.3(12) . . ?
C9 C10 H10A 110.5 . . ?
C11 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
C11 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C12 C11 C10 108.3(15) . . ?
C12 C11 H11A 110.0 . . ?
C10 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N1 115.2(10) . . ?
C14 C13 H13A 108.5 . . ?
N1 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
N1 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C13 C14 C15 110.3(14) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C17 C17 I1 124.0(13) 2_666 . ?
C17 C17 I2 123.4(13) 2_666 . ?
I1 C17 I2 112.6(6) . . ?
C18 C18 I4 120(2) 2_775 . ?
C18 C18 I3 128(2) 2_775 . ?
I4 C18 I3 111.3(7) . . ?
C1 N1 C5 113.1(10) . . ?
C1 N1 C13 108.0(9) . . ?
C5 N1 C13 108.4(9) . . ?
C1 N1 C9 107.3(8) . . ?
C5 N1 C9 108.2(9) . . ?
C13 N1 C9 112.0(10) . . ?
C16 C15 C14 108(2) . . ?
C16 C15 H15A 110.0 . . ?
C14 C15 H15A 110.1 . . ?
C16 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         1.556
_refine_diff_density_min         -2.070
_refine_diff_density_rms         0.319