# 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_111204d_0m
_database_code_depnum_ccdc_archive 'CCDC 908907'
#TrackingRef 'TIE-Br.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H36 Br I12 N'
_chemical_formula_weight         1917.23
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'
Br Br -0.2901 2.4595 '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           Tetragonal
_symmetry_space_group_name_H-M   I4/mmm
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'-x, y, -z'
'x, -y, -z'
'y, x, -z'
'-y, -x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y+1/2, x+1/2, -z+1/2'
'-y+1/2, -x+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'x, -y, z'
'-x, y, z'
'-y, -x, z'
'y, x, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'
_cell_length_a                   16.0167(7)
_cell_length_b                   16.0167(7)
_cell_length_c                   17.0905(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4384.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4279
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.46
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.905
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3384
_exptl_absorpt_coefficient_mu    9.402
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.0887
_exptl_absorpt_correction_T_max  0.1374
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      120(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            10712
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.25
_reflns_number_total             1161
_reflns_number_gt                1073
_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^)+(0.0594P)^2^+249.5142P] 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         1161
_refine_ls_number_parameters     68
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1406
_refine_ls_wR_factor_gt          0.1363
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_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
Br1 Br 0.0000 0.5000 0.5000 0.0484(10) Uani 1 8 d S . .
C1 C 0.5000 0.0763(8) 0.1976(9) 0.022(3) Uani 1 2 d S . .
H1A H 0.4501 0.0739 0.1634 0.027 Uiso 0.50 1 calc PR . .
H1B H 0.5499 0.0739 0.1634 0.027 Uiso 0.50 1 calc PR . .
C2 C 0.5000 0.1606(9) 0.2411(10) 0.034(4) Uani 1 2 d S . .
H2A H 0.4500 0.1641 0.2750 0.041 Uiso 0.50 1 calc PR . .
H2B H 0.5500 0.1641 0.2750 0.041 Uiso 0.50 1 calc PR . .
C3 C 0.5000 0.2320(9) 0.1850(11) 0.037(4) Uani 1 2 d S . .
H3A H 0.4501 0.2276 0.1511 0.044 Uiso 0.50 1 calc PR . .
H3B H 0.5499 0.2276 0.1511 0.044 Uiso 0.50 1 calc PR . .
C4 C 0.5000 0.3165(10) 0.2236(11) 0.044(4) Uani 1 2 d S . .
H4A H 0.5440 0.3184 0.2635 0.066 Uiso 0.50 1 calc PR . .
H4B H 0.4457 0.3263 0.2483 0.066 Uiso 0.50 1 calc PR . .
H4C H 0.5104 0.3597 0.1842 0.066 Uiso 0.50 1 calc PR . .
C5 C 0.540(2) 0.5000 1.0000 0.010(7) Uani 0.50 4 d SP . .
C6 C 0.7437(11) 0.7814(10) 0.9720(12) 0.020(4) Uani 0.50 1 d P . .
C7 C 0.970(2) 0.970(2) 1.0000 0.053(16) Uani 0.50 4 d SP . .
I1 I 0.61130(6) 0.61130(6) 1.0000 0.0317(4) Uani 1 4 d S . .
I2 I 0.64598(6) 0.87061(6) 1.0000 0.0457(4) Uani 1 2 d S . .
I3 I 0.76683(5) 0.76683(5) 0.85365(7) 0.0434(4) Uani 1 2 d S . .
I4 I 1.0000 0.84340(10) 1.0000 0.0721(8) Uani 1 4 d S . .
N1 N 0.5000 0.0000 0.2500 0.029(6) Uani 1 8 d S . .
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
Br1 0.0310(19) 0.038(2) 0.076(3) 0.000 0.000 0.000
C1 0.018(7) 0.015(7) 0.035(8) 0.006(6) 0.000 0.000
C2 0.043(9) 0.020(7) 0.039(9) 0.004(7) 0.000 0.000
C3 0.041(9) 0.013(7) 0.056(11) 0.002(7) 0.000 0.000
C4 0.053(11) 0.020(8) 0.059(11) 0.004(8) 0.000 0.000
C5 0.009(13) 0.012(14) 0.010(15) 0.000 0.000 0.000
C6 0.015(8) 0.006(7) 0.039(11) 0.000(6) 0.002(6) 0.005(6)
C7 0.016(13) 0.016(13) 0.13(5) 0.000 0.000 0.004(14)
I1 0.0201(5) 0.0201(5) 0.0549(9) 0.000 0.000 -0.0101(5)
I2 0.0104(5) 0.0130(5) 0.1138(11) 0.000 0.000 0.0037(4)
I3 0.0467(5) 0.0467(5) 0.0367(7) 0.0045(4) 0.0045(4) 0.0010(5)
I4 0.0275(9) 0.0140(8) 0.175(3) 0.000 0.000 0.000
N1 0.014(7) 0.014(7) 0.057(18) 0.000 0.000 0.000
_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 1.515(13) . ?
C1 C2 1.54(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.49(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.50(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C5 0.91(5) 19_567 ?
C5 C5 0.91(5) 3_655 ?
C5 C5 1.29(6) 17_667 ?
C5 I1 2.115(17) . ?
C5 I1 2.115(17) 19_567 ?
C6 C6 0.85(3) 24 ?
C6 C6 0.96(4) 18_557 ?
C6 C6 1.28(4) 7_557 ?
C6 I3 2.07(2) . ?
C6 I2 2.173(17) . ?
C7 C7 0.95(6) 19_577 ?
C7 C7 0.95(6) 3_755 ?
C7 C7 1.34(9) 17_777 ?
C7 I4 2.09(2) 19_577 ?
C7 I4 2.09(2) . ?
I1 C5 2.115(18) 3_655 ?
I2 C6 2.173(17) 18_557 ?
I3 C6 2.07(2) 24 ?
I4 C7 2.09(2) 3_755 ?
N1 C1 1.515(13) 27 ?
N1 C1 1.515(13) 28_545 ?
N1 C1 1.515(13) 2_655 ?
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 114.9(11) . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1B 108.5 . . ?
C2 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C3 C2 C1 111.2(13) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 114.0(15) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
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 . . ?
C5 C5 C5 90.000(4) 19_567 3_655 ?
C5 C5 C5 45.000(11) 19_567 17_667 ?
C5 C5 C5 45.000(11) 3_655 17_667 ?
C5 C5 I1 167.5(7) 19_567 . ?
C5 C5 I1 77.5(7) 3_655 . ?
C5 C5 I1 122.5(7) 17_667 . ?
C5 C5 I1 77.5(7) 19_567 19_567 ?
C5 C5 I1 167.5(7) 3_655 19_567 ?
C5 C5 I1 122.5(7) 17_667 19_567 ?
I1 C5 I1 114.9(15) . 19_567 ?
C6 C6 C6 90.000(3) 24 18_557 ?
C6 C6 C6 48.3(16) 24 7_557 ?
C6 C6 C6 41.7(16) 18_557 7_557 ?
C6 C6 I3 78.1(5) 24 . ?
C6 C6 I3 167.8(5) 18_557 . ?
C6 C6 I3 126.3(19) 7_557 . ?
C6 C6 I2 167.0(5) 24 . ?
C6 C6 I2 77.3(5) 18_557 . ?
C6 C6 I2 119(2) 7_557 . ?
I3 C6 I2 114.7(8) . . ?
C7 C7 C7 90.00(7) 19_577 3_755 ?
C7 C7 C7 45.00(3) 19_577 17_777 ?
C7 C7 C7 45.000(13) 3_755 17_777 ?
C7 C7 I4 76.9(11) 19_577 19_577 ?
C7 C7 I4 166.9(11) 3_755 19_577 ?
C7 C7 I4 121.9(11) 17_777 19_577 ?
C7 C7 I4 166.9(11) 19_577 . ?
C7 C7 I4 76.9(11) 3_755 . ?
C7 C7 I4 121.9(11) 17_777 . ?
I4 C7 I4 116(2) 19_577 . ?
C5 I1 C5 24.9(15) 3_655 . ?
C6 I2 C6 25.4(10) 18_557 . ?
C6 I3 C6 23.8(9) 24 . ?
C7 I4 C7 26(2) 3_755 . ?
C1 N1 C1 107.5(11) 27 28_545 ?
C1 N1 C1 110.5(6) 27 2_655 ?
C1 N1 C1 110.5(6) 28_545 2_655 ?
C1 N1 C1 110.5(6) 27 . ?
C1 N1 C1 110.5(6) 28_545 . ?
C1 N1 C1 107.5(11) 2_655 . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.556
_refine_diff_density_min         -5.125
_refine_diff_density_rms         0.313