# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Massimiliano Arca'
_publ_contact_author_email       marca@unica.it
loop_
_publ_author_name
F.Devillanova
C.Aragoni
M.Arca
M.B.Hursthouse
S.L.Huth

# Attachment '- 2.cif'

data_2006cgl0741
_database_code_depnum_ccdc_archive 'CCDC 829972'
#TrackingRef '- 2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'CAGLIARI 165'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 Br7 N2'
_chemical_formula_weight         840.69

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'

_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                   7.0558(3)
_cell_length_b                   13.6319(3)
_cell_length_c                   14.1191(5)
_cell_angle_alpha                106.205(2)
_cell_angle_beta                 95.292(2)
_cell_angle_gamma                104.352(2)
_cell_volume                     1244.22(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5401
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    11.297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1139
_exptl_absorpt_correction_T_max  0.2651
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22322
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5676
_reflns_number_gt                4147
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0313P)^2^+3.8854P] 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     SHELXL
_refine_ls_extinction_coef       0.0019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5676
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_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 0.5477(7) 0.0607(4) -0.2365(4) 0.0244(11) Uani 1 1 d . . .
C2 C 0.5113(7) -0.0452(4) -0.2419(4) 0.0238(11) Uani 1 1 d . . .
H2 H 0.4621 -0.0679 -0.1888 0.029 Uiso 1 1 calc R . .
C3 C 0.6183(7) -0.0883(4) -0.3952(4) 0.0266(12) Uani 1 1 d . . .
H3 H 0.6382 -0.1414 -0.4502 0.032 Uiso 1 1 calc R . .
C4 C 0.6666(8) 0.0163(4) -0.3939(4) 0.0290(12) Uani 1 1 d . . .
H4 H 0.7233 0.0369 -0.4464 0.035 Uiso 1 1 calc R . .
C5 C 0.6298(8) 0.0912(4) -0.3132(4) 0.0299(12) Uani 1 1 d . . .
H5 H 0.6613 0.1639 -0.3107 0.036 Uiso 1 1 calc R . .
C6 C 0.5085(8) 0.1364(4) -0.1470(4) 0.0298(12) Uani 1 1 d . . .
C7 C 0.3935(8) 0.1986(4) -0.1468(4) 0.0294(12) Uani 1 1 d . . .
C8 C 0.3595(8) 0.2769(4) -0.0580(4) 0.0273(12) Uani 1 1 d . . .
C9 C 0.1676(8) 0.2681(4) -0.0378(4) 0.0329(13) Uani 1 1 d . . .
H9 H 0.0597 0.2109 -0.0796 0.039 Uiso 1 1 calc R . .
C10 C 0.1337(8) 0.3422(4) 0.0428(4) 0.0273(12) Uani 1 1 d . . .
H10 H 0.0025 0.3357 0.0563 0.033 Uiso 1 1 calc R . .
C11 C 0.2908(7) 0.4268(4) 0.1046(4) 0.0220(10) Uani 1 1 d . . .
C12 C 0.4833(8) 0.4352(4) 0.0857(4) 0.0250(11) Uani 1 1 d . . .
H12 H 0.5913 0.4921 0.1280 0.030 Uiso 1 1 calc R . .
C13 C 0.5169(8) 0.3601(4) 0.0046(4) 0.0278(12) Uani 1 1 d . . .
H13 H 0.6484 0.3656 -0.0082 0.033 Uiso 1 1 calc R . .
C14 C 0.2560(7) 0.5083(4) 0.1906(4) 0.0231(11) Uani 1 1 d . . .
C15 C 0.3531(8) 0.5374(4) 0.2839(4) 0.0242(11) Uani 1 1 d . . .
C16 C 0.4934(8) 0.4834(4) 0.3167(4) 0.0248(11) Uani 1 1 d . . .
C17 C 0.4316(8) 0.3739(4) 0.3012(4) 0.0256(11) Uani 1 1 d . . .
H17 H 0.2979 0.3352 0.2712 0.031 Uiso 1 1 calc R . .
C18 C 0.7428(8) 0.3755(4) 0.3685(4) 0.0332(13) Uani 1 1 d . . .
H18 H 0.8308 0.3378 0.3851 0.040 Uiso 1 1 calc R . .
C19 C 0.8137(9) 0.4838(5) 0.3880(5) 0.0437(16) Uani 1 1 d . . .
H19 H 0.9479 0.5207 0.4185 0.052 Uiso 1 1 calc R . .
C20 C 0.6865(8) 0.5380(4) 0.3625(4) 0.0349(13) Uani 1 1 d . . .
H20 H 0.7321 0.6131 0.3765 0.042 Uiso 1 1 calc R . .
N1 N 0.5440(6) -0.1155(3) -0.3200(3) 0.0224(9) Uani 1 1 d . . .
H1N H 0.5154 -0.1828 -0.3223 0.027 Uiso 1 1 d R . .
N2 N 0.5542(7) 0.3212(3) 0.3271(3) 0.0293(10) Uani 1 1 d . . .
Br1 Br 0.64093(8) 0.13354(4) -0.02404(4) 0.02627(13) Uani 1 1 d . . .
Br2 Br 0.24664(8) 0.19033(4) -0.27146(4) 0.03023(14) Uani 1 1 d . . .
Br3 Br 0.06715(8) 0.57628(4) 0.15611(4) 0.03326(15) Uani 1 1 d . . .
Br4 Br 0.31805(9) 0.65055(4) 0.38752(4) 0.03555(16) Uani 1 1 d . . .
Br5 Br 0.96615(8) 0.19698(4) 0.49223(4) 0.03206(15) Uani 1 1 d . . .
Br6 Br 0.98281(7) 0.13631(4) 0.29953(4) 0.02819(14) Uani 1 1 d . . .
Br7 Br 1.00466(11) 0.07392(6) 0.12145(5) 0.0558(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
C1 0.021(3) 0.021(2) 0.034(3) 0.009(2) 0.007(2) 0.009(2)
C2 0.023(3) 0.019(2) 0.028(3) 0.008(2) 0.002(2) 0.004(2)
C3 0.024(3) 0.029(3) 0.024(3) 0.003(2) -0.001(2) 0.011(2)
C4 0.029(3) 0.035(3) 0.028(3) 0.015(2) 0.006(2) 0.013(2)
C5 0.027(3) 0.025(3) 0.042(3) 0.015(2) 0.007(2) 0.008(2)
C6 0.026(3) 0.025(3) 0.038(3) 0.011(2) 0.003(2) 0.005(2)
C7 0.028(3) 0.025(3) 0.037(3) 0.012(2) 0.005(2) 0.008(2)
C8 0.033(3) 0.020(3) 0.032(3) 0.010(2) 0.010(2) 0.010(2)
C9 0.024(3) 0.026(3) 0.043(3) 0.007(2) 0.004(2) 0.003(2)
C10 0.022(3) 0.029(3) 0.032(3) 0.007(2) 0.003(2) 0.011(2)
C11 0.023(3) 0.022(2) 0.025(3) 0.011(2) 0.003(2) 0.011(2)
C12 0.028(3) 0.022(3) 0.027(3) 0.011(2) 0.004(2) 0.007(2)
C13 0.028(3) 0.019(2) 0.039(3) 0.010(2) 0.013(2) 0.008(2)
C14 0.022(3) 0.018(2) 0.033(3) 0.008(2) 0.007(2) 0.011(2)
C15 0.031(3) 0.016(2) 0.027(3) 0.006(2) 0.011(2) 0.008(2)
C16 0.036(3) 0.020(2) 0.021(3) 0.010(2) 0.004(2) 0.009(2)
C17 0.032(3) 0.016(2) 0.029(3) 0.008(2) 0.005(2) 0.007(2)
C18 0.032(3) 0.035(3) 0.035(3) 0.018(3) -0.004(3) 0.009(2)
C19 0.039(3) 0.044(4) 0.047(4) 0.026(3) -0.011(3) 0.004(3)
C20 0.036(3) 0.024(3) 0.040(3) 0.016(2) -0.005(3) -0.002(2)
N1 0.021(2) 0.017(2) 0.028(2) 0.0064(17) -0.0031(18) 0.0075(17)
N2 0.042(3) 0.020(2) 0.030(2) 0.0105(19) 0.003(2) 0.012(2)
Br1 0.0306(3) 0.0244(3) 0.0259(3) 0.0103(2) -0.0008(2) 0.0109(2)
Br2 0.0345(3) 0.0346(3) 0.0275(3) 0.0112(2) 0.0007(2) 0.0203(2)
Br3 0.0324(3) 0.0379(3) 0.0407(3) 0.0163(2) 0.0110(2) 0.0237(2)
Br4 0.0552(4) 0.0216(3) 0.0324(3) 0.0071(2) 0.0166(3) 0.0137(2)
Br5 0.0363(3) 0.0296(3) 0.0326(3) 0.0091(2) 0.0090(2) 0.0130(2)
Br6 0.0220(3) 0.0300(3) 0.0353(3) 0.0119(2) 0.0013(2) 0.0118(2)
Br7 0.0655(5) 0.0837(5) 0.0300(3) 0.0178(3) 0.0033(3) 0.0440(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
C1 C2 1.380(7) . ?
C1 C5 1.389(7) . ?
C1 C6 1.489(7) . ?
C2 N1 1.325(6) . ?
C2 H2 0.9500 . ?
C3 N1 1.328(7) . ?
C3 C4 1.376(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(7) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.311(7) . ?
C6 Br1 1.909(6) . ?
C7 C8 1.485(7) . ?
C7 Br2 1.918(5) . ?
C8 C13 1.392(7) . ?
C8 C9 1.393(7) . ?
C9 C10 1.378(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(7) . ?
C11 C14 1.485(7) . ?
C12 C13 1.390(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.331(7) . ?
C14 Br3 1.902(5) . ?
C15 C16 1.484(7) . ?
C15 Br4 1.891(5) . ?
C16 C20 1.376(7) . ?
C16 C17 1.395(7) . ?
C17 N2 1.339(6) . ?
C17 H17 0.9500 . ?
C18 N2 1.337(7) . ?
C18 C19 1.375(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(8) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
N1 H1N 0.8800 . ?
Br5 Br6 2.6367(8) . ?
Br6 Br7 2.4518(9) . ?

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 C1 C5 117.4(5) . . ?
C2 C1 C6 118.7(5) . . ?
C5 C1 C6 123.8(5) . . ?
N1 C2 C1 120.9(5) . . ?
N1 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
N1 C3 C4 120.3(5) . . ?
N1 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 118.0(5) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C1 C5 C4 120.8(5) . . ?
C1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C1 126.6(5) . . ?
C7 C6 Br1 120.6(5) . . ?
C1 C6 Br1 112.8(4) . . ?
C6 C7 C8 126.8(5) . . ?
C6 C7 Br2 119.1(4) . . ?
C8 C7 Br2 114.2(4) . . ?
C13 C8 C9 119.4(5) . . ?
C13 C8 C7 120.8(5) . . ?
C9 C8 C7 119.8(5) . . ?
C10 C9 C8 120.2(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.4(5) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.7(5) . . ?
C12 C11 C14 119.3(4) . . ?
C10 C11 C14 121.0(4) . . ?
C13 C12 C11 119.7(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C8 120.5(5) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C15 C14 C11 124.5(4) . . ?
C15 C14 Br3 121.1(4) . . ?
C11 C14 Br3 114.4(4) . . ?
C14 C15 C16 123.6(4) . . ?
C14 C15 Br4 122.2(4) . . ?
C16 C15 Br4 114.2(4) . . ?
C20 C16 C17 117.7(5) . . ?
C20 C16 C15 122.1(4) . . ?
C17 C16 C15 120.1(5) . . ?
N2 C17 C16 122.3(5) . . ?
N2 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
N2 C18 C19 122.3(5) . . ?
N2 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C20 118.8(5) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C16 C20 C19 120.1(5) . . ?
C16 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C2 N1 C3 122.6(4) . . ?
C2 N1 H1N 118.7 . . ?
C3 N1 H1N 118.7 . . ?
C18 N2 C17 118.8(4) . . ?
Br7 Br6 Br5 177.52(3) . . ?

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
N1 H1N N2 0.88 1.81 2.689(6) 177.6 2_655

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.353
_refine_diff_density_min         -1.247
_refine_diff_density_rms         0.151


data_2005slh0245
_database_code_depnum_ccdc_archive 'CCDC 837144'
#TrackingRef '- 1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2005slh0245/132
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 I5.50 N2'
_chemical_formula_weight         978.27

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-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                   26.670(5)
_cell_length_b                   8.4146(17)
_cell_length_c                   13.050(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.49(3)
_cell_angle_gamma                90.00
_cell_volume                     2573.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3160
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       'cut fragment'
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1750
_exptl_absorpt_coefficient_mu    6.650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4562
_exptl_absorpt_correction_T_max  0.7768
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
The values for minimum and maximum transmission are based
on the cell dimensions only and were generated using the
size command in SHELX. SADABS estimates the ratio of minimum
to maximum transmission as 0.808517
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BrukerNonius 95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26776
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2948
_reflns_number_gt                2665
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.

The structure was modeled using 'whole molecule disorder' with
the ratio refining to 87%:13%.
The interaction of ligand and I2 forms a sheet-like structure.
The structure also contains solvent accessible cavities, which are occupied
to approximately 70% by diiodine units, which show a small amount of
movement modeled as disorder in the ratio 9%:61%
The missing 30% could not be resolved and modelling the
remaining electron density in this cavity area
(two peaks) did not yield a chemically or crystallographically
sensible moiety and is hence left as unrefined.
SQUEEZE was applied to (1) the structure presented and whilst some
residual density was identified and removed from the intensity data
the two residual density peaks remained and the R-factor was unaffected.
SQUEEZE was also applied to (2) a model where the electron density in
the cavities was not refined at all. This only removed the density
associated with the diiodine but the difference map showed the same two
residual peaks as before.

This phenomenon was observed repeatedly in the crystals of this species.

Close inspection of the precession images corresponding to h0l, h1l and
h2l showed systematic diffuse scattering (images provided as ESI)
indicating that adequate modeling of this structure requires more
specialist treatment than is available with SHELX.
David Rae, specialist in prototype structures, was consequently
consulted and this phenomenon is being further investigated using
the RAELS08 constrained least squares refinement program.
The existence of two prototype structures of different space group
symmetry has since been established and the full details of this
crystallographic study are to be published in due course.
The cif presented here corresponds to the best fit that can be achieved
with a disorder model in SHELXL-97.

At present the model cannot be improved any further and an
appropriate comment has been included in the manuscript.

;

_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^)+(0.0614P)^2^+60.1757P] 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         2948
_refine_ls_number_parameters     148
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_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 0.1365(3) 0.3977(9) 0.7939(6) 0.0190(14) Uani 0.87 1 d PD A 1
H1 H 0.1239 0.2966 0.7585 0.023 Uiso 0.87 1 calc PR A 1
C2 C 0.1238(3) 0.5311(8) 0.7238(6) 0.0162(14) Uani 0.87 1 d PD A 1
C3 C 0.1427(3) 0.6800(9) 0.7763(6) 0.0216(15) Uani 0.87 1 d PD A 1
H3 H 0.1349 0.7731 0.7300 0.026 Uiso 0.87 1 calc PR A 1
C4 C 0.1728(3) 0.6891(9) 0.8966(6) 0.0224(15) Uani 0.87 1 d PD A 1
H4 H 0.1858 0.7889 0.9341 0.027 Uiso 0.87 1 calc PR A 1
C5 C 0.1838(3) 0.5504(9) 0.9625(6) 0.0226(15) Uani 0.87 1 d PD A 1
H5 H 0.2042 0.5570 1.0451 0.027 Uiso 0.87 1 calc PR A 1
N1 N 0.1663(3) 0.4078(7) 0.9114(5) 0.0194(12) Uani 0.87 1 d PD A 1
I1 I 0.183170(19) 0.18213(6) 1.03055(4) 0.01995(15) Uani 0.87 1 d PD B 1
I2 I 0.20381(2) -0.07365(6) 1.18509(4) 0.02416(16) Uani 0.87 1 d PD B 1
C21 C 0.1371(15) 0.605(3) 0.790(2) 0.0190(14) Uani 0.13 1 d PGD A 2
H21 H 0.1244 0.7056 0.7536 0.023 Uiso 0.13 1 calc PR A 2
C22 C 0.1251(15) 0.468(3) 0.7225(18) 0.0162(14) Uani 0.13 1 d PGD A 2
C23 C 0.1437(15) 0.321(3) 0.776(2) 0.0216(15) Uani 0.13 1 d PGD A 2
H23 H 0.1355 0.2280 0.7297 0.026 Uiso 0.13 1 calc PR A 2
C24 C 0.1744(15) 0.311(2) 0.897(2) 0.0224(15) Uani 0.13 1 d PGD A 2
H24 H 0.1872 0.2106 0.9331 0.027 Uiso 0.13 1 calc PR A 2
C25 C 0.1865(14) 0.448(3) 0.9642(18) 0.0226(15) Uani 0.13 1 d PGD A 2
H25 H 0.2074 0.4407 1.0467 0.027 Uiso 0.13 1 calc PR A 2
N2 N 0.1678(13) 0.595(2) 0.911(2) 0.0194(12) Uani 0.13 1 d PGD A 2
I4 I 0.18303(13) 0.8165(4) 1.0309(2) 0.01995(15) Uani 0.13 1 d PD A 2
I5 I 0.20453(14) 1.0718(4) 1.1860(3) 0.02416(16) Uani 0.13 1 d PD A 2
C6 C 0.0918(3) 0.5142(9) 0.5993(5) 0.0215(13) Uani 1 1 d . . .
C7 C 0.0644(3) 0.5073(9) 0.4963(6) 0.0235(13) Uani 1 1 d . A .
C8 C 0.0316(3) 0.5057(9) 0.3709(5) 0.0222(13) Uani 1 1 d . . .
C9 C 0.0158(3) 0.3651(9) 0.3106(6) 0.0278(15) Uani 1 1 d . . .
H9 H 0.0265 0.2672 0.3518 0.033 Uiso 1 1 calc R . .
C10 C 0.0157(3) 0.6500(9) 0.3107(5) 0.0240(13) Uani 1 1 d . . .
H10 H 0.0263 0.7476 0.3522 0.029 Uiso 1 1 calc R . .
I3 I 0.05704(4) -0.03023(13) 1.05688(8) 0.0263(2) Uani 0.61 1 d P . .
I3' I 0.05611(19) 0.0398(9) 1.0581(6) 0.0327(17) Uani 0.09 1 d PD . .

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 0.022(3) 0.021(4) 0.015(3) -0.004(3) 0.010(3) -0.003(3)
C2 0.015(3) 0.025(4) 0.011(3) -0.002(3) 0.008(2) 0.001(3)
C3 0.026(4) 0.018(4) 0.020(3) 0.000(3) 0.009(3) -0.004(3)
C4 0.029(4) 0.021(4) 0.017(3) -0.006(3) 0.011(3) -0.009(3)
C5 0.021(3) 0.029(4) 0.016(3) -0.003(3) 0.007(3) 0.001(3)
N1 0.019(3) 0.024(3) 0.014(3) 0.001(2) 0.007(2) 0.000(2)
I1 0.0203(2) 0.0240(3) 0.0140(2) 0.00168(16) 0.00692(18) 0.00356(17)
I2 0.0268(3) 0.0252(3) 0.0192(2) 0.00589(18) 0.0099(2) 0.00416(18)
C21 0.022(3) 0.021(4) 0.015(3) -0.004(3) 0.010(3) -0.003(3)
C22 0.015(3) 0.025(4) 0.011(3) -0.002(3) 0.008(2) 0.001(3)
C23 0.026(4) 0.018(4) 0.020(3) 0.000(3) 0.009(3) -0.004(3)
C24 0.029(4) 0.021(4) 0.017(3) -0.006(3) 0.011(3) -0.009(3)
C25 0.021(3) 0.029(4) 0.016(3) -0.003(3) 0.007(3) 0.001(3)
N2 0.019(3) 0.024(3) 0.014(3) 0.001(2) 0.007(2) 0.000(2)
I4 0.0203(2) 0.0240(3) 0.0140(2) 0.00168(16) 0.00692(18) 0.00356(17)
I5 0.0268(3) 0.0252(3) 0.0192(2) 0.00589(18) 0.0099(2) 0.00416(18)
C6 0.015(3) 0.034(4) 0.013(3) 0.003(2) 0.005(2) 0.002(2)
C7 0.023(3) 0.036(4) 0.015(3) -0.003(3) 0.012(3) -0.002(3)
C8 0.017(3) 0.041(4) 0.009(3) 0.000(3) 0.007(2) -0.001(3)
C9 0.030(3) 0.035(4) 0.016(3) 0.003(3) 0.008(3) 0.001(3)
C10 0.020(3) 0.032(4) 0.018(3) -0.001(3) 0.007(3) -0.002(3)
I3 0.0286(4) 0.0220(5) 0.0230(4) -0.0009(4) 0.0080(3) -0.0029(4)
I3' 0.044(4) 0.019(3) 0.031(3) 0.009(3) 0.015(3) 0.016(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
C1 N1 1.352(8) . ?
C1 C2 1.383(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(9) . ?
C2 C6 1.438(9) . ?
C3 C4 1.383(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(10) . ?
C4 H4 0.9500 . ?
C5 N1 1.344(9) . ?
C5 H5 0.9500 . ?
I1 I2 2.8184(8) . ?
C21 C22 1.3900 . ?
C21 N2 1.3900 . ?
C21 H21 0.9500 . ?
C22 C23 1.3900 . ?
C22 C6 1.47(2) . ?
C23 C24 1.3900 . ?
C23 H23 0.9500 . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C25 N2 1.3900 . ?
C25 H25 0.9500 . ?
N2 I4 2.344(14) . ?
I4 I5 2.816(5) . ?
C6 C7 1.186(9) . ?
C7 C8 1.441(8) . ?
C8 C9 1.371(11) . ?
C8 C10 1.397(10) . ?
C9 C9 1.394(13) 2 ?
C9 H9 0.9500 . ?
C10 C10 1.394(12) 2 ?
C10 H10 0.9500 . ?
I3 I3 2.722(2) 5_557 ?
I3' I3' 2.716(9) 5_557 ?

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 121.7(6) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C1 C2 C3 119.0(6) . . ?
C1 C2 C6 119.5(6) . . ?
C3 C2 C6 121.5(6) . . ?
C4 C3 C2 118.9(6) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 119.4(6) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.3(6) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 N1 C1 119.7(6) . . ?
C22 C21 N2 120.0 . . ?
C22 C21 H21 120.0 . . ?
N2 C21 H21 120.0 . . ?
C23 C22 C21 120.0 . . ?
C23 C22 C6 131.8(16) . . ?
C21 C22 C6 108.2(17) . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 N2 120.0 . . ?
C24 C25 H25 120.0 . . ?
N2 C25 H25 120.0 . . ?
C25 N2 C21 120.0 . . ?
C25 N2 I4 117.9(13) . . ?
C21 N2 I4 121.9(13) . . ?
N2 I4 I5 176.8(7) . . ?
C7 C6 C2 176.9(8) . . ?
C7 C6 C22 162.0(12) . . ?
C2 C6 C22 20.9(10) . . ?
C6 C7 C8 177.6(8) . . ?
C9 C8 C10 119.9(6) . . ?
C9 C8 C7 120.9(7) . . ?
C10 C8 C7 119.2(6) . . ?
C8 C9 C9 120.4(4) . 2 ?
C8 C9 H9 119.8 . . ?
C9 C9 H9 119.8 2 . ?
C10 C10 C8 119.7(4) 2 . ?
C10 C10 H10 120.1 2 . ?
C8 C10 H10 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         5.584
_refine_diff_density_min         -1.791
_refine_diff_density_rms         0.261