# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2010

data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145

_publ_contact_author_name        'Simona Fantacci'
_publ_contact_author_address     
;
Via Elce di Sotto, 8
Perugia
06123
;

_publ_contact_author_email       simona@thch.unipg.it
_publ_contact_author             'Dr. N. Casati'
_publ_requested_category         FO
loop_
_publ_author_name
S.Fantacci
F.Nunzi
E.Cariati
E.Tordin
N.Casati
P.Macchi

# Attachment 'Casati.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2009-05-25 at 12:58:59
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\wingx\files\archive.dat
# CIF files read : ele65c

data_ele65c
_database_code_depnum_ccdc_archive 'CCDC 733632'
#TrackingRef 'Casati.cif'

_audit_creation_date             2009-05-25T12:58:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C16 H19 I N2'
_chemical_formula_weight         366.23
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

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'

_cell_length_a                   8.777(2)
_cell_length_b                   34.912(7)
_cell_length_c                   6.2800(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.459(2)
_cell_angle_gamma                90
_cell_volume                     1924.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.657
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  0.92

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.037
_diffrn_reflns_number            7486
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             3727
_reflns_number_gt                2825
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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^)+(0.0996P)^2^+0.8198P] 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_number_reflns         3727
_refine_ls_number_parameters     59
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1859
_refine_ls_wR_factor_gt          0.1766
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(6)
_refine_diff_density_max         0.87
_refine_diff_density_min         -0.57
_refine_diff_density_rms         0.096

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'

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
N1 N 0.5635(7) 0.28395(15) 0.0379(7) 0.0614(16) Uiso 1 1 d G . .
C2 C 0.4187(6) 0.2919(2) 0.1141(11) 0.072(3) Uiso 1 1 d G . .
H2 H 0.3332 0.2833 0.04 0.086 Uiso 1 1 calc R . .
C3 C 0.4017(7) 0.3128(2) 0.3008(12) 0.070(3) Uiso 1 1 d G . .
H3 H 0.3048 0.3181 0.3517 0.084 Uiso 1 1 calc R . .
C4 C 0.5295(9) 0.32571(17) 0.4114(9) 0.070(2) Uiso 1 1 d G . .
C5 C 0.6744(8) 0.3177(2) 0.3353(11) 0.084(4) Uiso 1 1 d G . .
H5 H 0.7599 0.3264 0.4093 0.1 Uiso 1 1 calc R . .
C6 C 0.6914(6) 0.2969(2) 0.1486(11) 0.082(3) Uiso 1 1 d G . .
H6 H 0.7883 0.2915 0.0976 0.098 Uiso 1 1 calc R . .
C11 C 0.5289(10) 0.38679(19) 0.9133(8) 0.081(3) Uiso 1 1 d G . .
C12 C 0.6615(7) 0.3989(2) 1.0154(11) 0.083(3) Uiso 1 1 d G . .
H12 H 0.756 0.3923 0.9606 0.1 Uiso 1 1 calc R . .
C13 C 0.6527(5) 0.4209(2) 1.1995(11) 0.087(3) Uiso 1 1 d G . .
H13 H 0.7414 0.429 1.2679 0.104 Uiso 1 1 calc R . .
C14 C 0.5114(6) 0.43072(15) 1.2815(8) 0.0463(17) Uiso 1 1 d G . .
C15 C 0.3788(5) 0.4186(2) 1.1794(12) 0.097(4) Uiso 1 1 d G . .
H15 H 0.2843 0.4252 1.2343 0.117 Uiso 1 1 calc R . .
C16 C 0.3876(8) 0.3966(3) 0.9953(12) 0.105(4) Uiso 1 1 d G . .
H16 H 0.2989 0.3885 0.927 0.126 Uiso 1 1 calc R . .
C20 C 0.6428(18) 0.4654(5) 1.569(3) 0.111(5) Uiso 1 1 d . . .
H20A H 0.6192 0.4806 1.6913 0.166 Uiso 1 1 calc R . .
H20B H 0.703 0.4802 1.4718 0.166 Uiso 1 1 calc R . .
H20C H 0.6991 0.4431 1.6123 0.166 Uiso 1 1 calc R . .
C21 C 0.332(2) 0.4590(5) 1.552(3) 0.126(5) Uiso 1 1 d . . .
H21A H 0.3374 0.4749 1.6767 0.189 Uiso 1 1 calc R . .
H21B H 0.2889 0.4346 1.5891 0.189 Uiso 1 1 calc R . .
H21C H 0.268 0.4712 1.4469 0.189 Uiso 1 1 calc R . .
N2 N 0.4966(14) 0.4531(3) 1.459(2) 0.104(3) Uiso 1 1 d . . .
I1 I 0.04577(16) 0.312437(16) 0.79947(16) 0.0825(3) Uani 1 1 d . . .
C10 C 0.5812(15) 0.2624(3) -0.1487(18) 0.092(4) Uiso 1 1 d . . .
H10A H 0.6877 0.2597 -0.179 0.138 Uiso 1 1 calc R . .
H10B H 0.5314 0.2753 -0.2651 0.138 Uiso 1 1 calc R . .
H10C H 0.5366 0.2376 -0.1298 0.138 Uiso 1 1 calc R . .
C7' C 0.5810(15) 0.3638(3) 0.7323(18) 0.087(3) Uiso 1 1 d . . .
H7' H 0.6852 0.3611 0.7118 0.104 Uiso 1 1 calc R . .
C7 C 0.4912(14) 0.3477(3) 0.6031(19) 0.084(3) Uiso 1 1 d . . .
H7 H 0.388 0.3499 0.6328 0.101 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 0.0674(3) 0.0965(4) 0.0835(4) -0.0183(4) -0.0043(4) 0.0007(5)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
N1 C2 1.39 . ?
N1 C6 1.39 . ?
N1 C10 1.401(12) . ?
C2 C3 1.39 . ?
C3 C4 1.39 . ?
C4 C5 1.39 . ?
C4 C7 1.469(13) . ?
C5 C6 1.39 . ?
C11 C12 1.39 . ?
C11 C16 1.39 . ?
C11 C7' 1.467(12) . ?
C12 C13 1.39 . ?
C13 C14 1.39 . ?
C14 N2 1.369(14) . ?
C14 C15 1.39 . ?
C15 C16 1.39 . ?
C20 N2 1.513(18) . ?
C21 N2 1.58(2) . ?
C7' C7 1.260(16) . ?

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 N1 C6 120 . . ?
C2 N1 C10 120.2(7) . . ?
C6 N1 C10 119.8(7) . . ?
N1 C2 C3 120 . . ?
C4 C3 C2 120 . . ?
C5 C4 C3 120 . . ?
C5 C4 C7 127.1(7) . . ?
C3 C4 C7 112.9(7) . . ?
C4 C5 C6 120 . . ?
C5 C6 N1 120 . . ?
C12 C11 C16 120 . . ?
C12 C11 C7' 105.0(7) . . ?
C16 C11 C7' 135.0(7) . . ?
C13 C12 C11 120 . . ?
C14 C13 C12 120 . . ?
N2 C14 C13 122.3(6) . . ?
N2 C14 C15 117.7(6) . . ?
C13 C14 C15 120 . . ?
C16 C15 C14 120 . . ?
C15 C16 C11 120 . . ?
C14 N2 C20 116.5(10) . . ?
C14 N2 C21 117.9(12) . . ?
C20 N2 C21 124.9(13) . . ?
C7 C7' C11 123.1(11) . . ?
C7' C7 C4 128.0(11) . . ?