# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_100K
_database_code_depnum_ccdc_archive 'CCDC 1022215'
_audit_update_record             
;
2014-09-01 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 I4 N4'
_chemical_formula_sum            'C12 H20 I8 N8'
_chemical_formula_weight         1291.56

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'-x-1/2, y-1/2, z'
'x-1/2, -y-1/2, z'

_cell_length_a                   13.884(4)
_cell_length_b                   27.640(8)
_cell_length_c                   7.651(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2936.1(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10519
_cell_measurement_theta_min      2.9380
_cell_measurement_theta_max      28.7655

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.922
_exptl_crystal_F_000             2288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2345
_exptl_crystal_size_mid          0.1512
_exptl_crystal_size_min          0.0932
_exptl_absorpt_coefficient_mu    8.467
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.209
_exptl_absorpt_correction_T_max  0.522
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28c (release 15-05-2013 CrysAlis171 .NET)
(compiled May 15 2013,09:16:53)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            23766
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.934
_diffrn_reflns_theta_max         28.749
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3899
_reflns_number_gt                3043
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0311P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.000252(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3899
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0604
_refine_ls_wR_factor_gt          0.0575
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I11 I 0.27246(2) 0.07964(2) 0.5000 0.01593(9) Uani 1 2 d S T P . .
I12 I 0.52443(3) 0.08838(2) 0.5000 0.02292(9) Uani 1 2 d S T P . .
I13 I 0.72632(3) 0.08897(2) 0.5000 0.02328(10) Uani 1 2 d S T P . .
I14 I 0.96238(2) 0.08490(2) 0.5000 0.01659(8) Uani 1 2 d S T P . .
I21 I 0.27922(2) 0.16445(2) 0.0000 0.01569(8) Uani 1 2 d S T P . .
I22 I 0.52977(3) 0.16942(2) 0.0000 0.02302(9) Uani 1 2 d S T P . .
I23 I 0.73134(3) 0.16746(2) 0.0000 0.02335(10) Uani 1 2 d S T P . .
I24 I 0.96837(3) 0.16111(2) 0.0000 0.01667(8) Uani 1 2 d S T P . .
N11 N 0.8878(2) 0.03998(11) 0.0877(4) 0.0219(7) Uani 1 1 d . . . . .
H11 H 0.8953 0.0656 0.1548 0.026 Uiso 1 1 calc R U . . .
C15 C 0.8745(3) -0.00512(13) 0.1435(6) 0.0241(9) Uani 1 1 d . . . . .
H15 H 0.8714 -0.0152 0.2620 0.029 Uiso 1 1 calc R U . . .
C14 C 0.8662(4) -0.03448(19) 0.0000 0.0259(13) Uani 1 2 d S T P . .
H14 H 0.8566 -0.0685 0.0000 0.031 Uiso 1 2 calc R U P . .
N21 N 0.3654(2) 0.04695(10) 0.0870(4) 0.0188(6) Uani 1 1 d . . . . .
H21 H 0.3589 0.0727 0.1536 0.023 Uiso 1 1 calc R U . . .
C25 C 0.3769(3) 0.00191(12) 0.1445(6) 0.0223(9) Uani 1 1 d . . . . .
H25 H 0.3799 -0.0080 0.2632 0.027 Uiso 1 1 calc R U . . .
C24 C 0.3836(4) -0.02780(18) 0.0000 0.0253(13) Uani 1 2 d S T P . .
H24 H 0.3914 -0.0619 0.0000 0.030 Uiso 1 2 calc R U P . .
N31 N 0.4001(2) 0.29268(10) 0.4132(4) 0.0205(7) Uani 1 1 d . . . . .
H31 H 0.4082 0.3183 0.3467 0.025 Uiso 1 1 calc R U . . .
C35 C 0.3859(3) 0.24780(13) 0.3557(6) 0.0248(9) Uani 1 1 d . . . . .
H35 H 0.3827 0.2379 0.2369 0.030 Uiso 1 1 calc R U . . .
C34 C 0.3768(4) 0.21822(19) 0.5000 0.0251(12) Uani 1 2 d S T P . .
H34 H 0.3663 0.1843 0.5000 0.030 Uiso 1 2 calc R U P . .
N41 N 0.1564(2) 0.19067(11) 0.4143(4) 0.0234(7) Uani 1 1 d . . . . .
H41 H 0.1675 0.1652 0.3483 0.028 Uiso 1 1 calc R U . . .
C45 C 0.1373(3) 0.23458(14) 0.3552(5) 0.0259(9) Uani 1 1 d . . . . .
H45 H 0.1335 0.2444 0.2364 0.031 Uiso 1 1 calc R U . . .
C44 C 0.1239(4) 0.2631(2) 0.5000 0.0291(13) Uani 1 2 d S T P . .
H44 H 0.1081 0.2965 0.5000 0.035 Uiso 1 2 calc R U P . .


_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
I12 I13 2.8031(10) . ?
I22 I23 2.7991(10) . ?
N11 C15 1.330(4) . ?
N11 N11 1.343(6) 6 ?
N11 H11 0.8800 . ?
C15 C14 1.370(5) . ?
C15 H15 0.9500 . ?
C14 C15 1.370(5) 6 ?
C14 H14 0.9500 . ?
N21 C25 1.330(4) . ?
N21 N21 1.332(5) 6 ?
N21 H21 0.8800 . ?
C25 C24 1.380(5) . ?
C25 H25 0.9500 . ?
C24 C25 1.380(5) 6 ?
C24 H24 0.9500 . ?
N31 N31 1.328(6) 6_556 ?
N31 C35 1.331(4) . ?
N31 H31 0.8800 . ?
C35 C34 1.379(5) . ?
C35 H35 0.9500 . ?
C34 C35 1.380(5) 6_556 ?
C34 H34 0.9500 . ?
N41 N41 1.312(6) 6_556 ?
N41 C45 1.322(5) . ?
N41 H41 0.8800 . ?
C45 C44 1.372(5) . ?
C45 H45 0.9500 . ?
C44 C45 1.372(5) 6_556 ?
C44 H44 0.9500 . ?

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
C15 N11 N11 108.7(2) . 6 ?
C15 N11 H11 125.7 . . ?
N11 N11 H11 125.7 6 . ?
N11 C15 C14 108.1(4) . . ?
N11 C15 H15 126.0 . . ?
C14 C15 H15 126.0 . . ?
C15 C14 C15 106.5(5) . 6 ?
C15 C14 H14 126.8 . . ?
C15 C14 H14 126.8 6 . ?
C25 N21 N21 109.3(2) . 6 ?
C25 N21 H21 125.3 . . ?
N21 N21 H21 125.3 6 . ?
N21 C25 C24 107.5(4) . . ?
N21 C25 H25 126.3 . . ?
C24 C25 H25 126.3 . . ?
C25 C24 C25 106.4(5) 6 . ?
C25 C24 H24 126.8 6 . ?
C25 C24 H24 126.8 . . ?
N31 N31 C35 109.3(2) 6_556 . ?
N31 N31 H31 125.3 6_556 . ?
C35 N31 H31 125.3 . . ?
N31 C35 C34 107.5(4) . . ?
N31 C35 H35 126.2 . . ?
C34 C35 H35 126.2 . . ?
C35 C34 C35 106.3(5) . 6_556 ?
C35 C34 H34 126.9 . . ?
C35 C34 H34 126.9 6_556 . ?
N41 N41 C45 110.0(2) 6_556 . ?
N41 N41 H41 125.0 6_556 . ?
C45 N41 H41 125.0 . . ?
N41 C45 C44 106.2(4) . . ?
N41 C45 H45 126.9 . . ?
C44 C45 H45 126.9 . . ?
C45 C44 C45 107.7(5) . 6_556 ?
C45 C44 H44 126.2 . . ?
C45 C44 H44 126.2 6_556 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 N11 C15 C14 0.2(4) 6 . . . ?
N11 C15 C14 C15 -0.3(6) . . . 6 ?
N21 N21 C25 C24 -0.5(4) 6 . . . ?
N21 C25 C24 C25 0.8(6) . . . 6 ?
N31 N31 C35 C34 -0.1(4) 6_556 . . . ?
N31 C35 C34 C35 0.2(6) . . . 6_556 ?
N41 N41 C45 C44 -0.6(4) 6_556 . . . ?
N41 C45 C44 C45 0.9(6) . . . 6_556 ?

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
N11 H11 I14 0.88 2.85 3.544(3) 136.8 .
N11 H11 I24 0.88 3.07 3.593(3) 120.4 .
N21 H21 I11 0.88 2.92 3.531(3) 128.4 .
N21 H21 I21 0.88 3.01 3.525(3) 119.6 .
N31 H31 I14 0.88 3.02 3.555(3) 121.4 3_456
N31 H31 I24 0.88 2.84 3.539(3) 137.7 3_455
N41 H41 I21 0.88 3.08 3.672(3) 126.1 .
N41 H41 I11 0.88 3.01 3.528(3) 119.5 .

_refine_diff_density_max         0.995
_refine_diff_density_min         -1.258
_refine_diff_density_rms         0.175

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_295k
_database_code_depnum_ccdc_archive 'CCDC 1022217'
_audit_update_record             
;
2014-09-01 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 I4 N4'
_chemical_formula_sum            'C6 H10 I4 N4'
_chemical_formula_weight         645.78

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           74
_space_group_name_H-M_alt        'I m m a'
_space_group_name_Hall           '-I 2b 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z'
'x, -y, -z'
'-x, y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z'
'-x, y, z'
'x, -y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y, z+1/2'

_cell_length_a                   14.162(6)
_cell_length_b                   7.913(3)
_cell_length_c                   13.627(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1527.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3443
_cell_measurement_theta_min      2.8700
_cell_measurement_theta_max      36.6616

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.809
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2767
_exptl_crystal_size_mid          0.1722
_exptl_crystal_size_min          0.0963
_exptl_absorpt_coefficient_mu    8.139
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.203
_exptl_absorpt_correction_T_max  0.556
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            8764
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.877
_diffrn_reflns_theta_max         36.760
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1847
_reflns_number_gt                1034
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+1.7745P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0046(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1847
_refine_ls_number_parameters     61
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.003
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.5000 0.2500 0.41153(4) 0.0714(3) Uani 1 4 d S T P . .
I2 I 0.20943(4) 0.2500 0.41793(3) 0.0749(2) Uani 1 2 d S T P . .
I3 I 0.0000 0.2500 0.42132(4) 0.0845(3) Uani 1 4 d S T P . .
N1 N 0.1217(14) 0.803(2) 0.1474(11) 0.082(5) Uani 0.2 1 d . . P A -1
H1N H 0.1249 0.8367 0.0875 0.098 Uiso 0.2 1 calc R U P A -1
N2 N 0.1220(14) 0.908(2) 0.2251(11) 0.076(4) Uani 0.2 1 d . . P A -1
H2N H 0.1174 1.0167 0.2235 0.091 Uiso 0.2 1 calc R U P A -1
N3 N 0.1307(16) 0.811(2) 0.3064(10) 0.080(4) Uani 0.2 1 d . . P A -1
H3N H 0.1366 0.8429 0.3664 0.096 Uiso 0.2 1 calc R U P A -1
N4 N 0.1279(13) 0.645(3) 0.2687(16) 0.103(5) Uani 0.2 1 d . . P A -1
H4N H 0.1329 0.5555 0.3037 0.124 Uiso 0.2 1 calc R U P A -1
N5 N 0.1163(16) 0.647(3) 0.173(2) 0.104(6) Uani 0.2 1 d . . P A -1
H5N H 0.1071 0.5612 0.1349 0.125 Uiso 0.2 1 calc R U P A -1
C1 C 0.1217(14) 0.803(2) 0.1474(11) 0.082(5) Uani 0.3 1 d . U P B -2
H1C H 0.1251 0.8395 0.0826 0.098 Uiso 0.3 1 calc R U P B -2
C2 C 0.1220(14) 0.908(2) 0.2251(11) 0.076(4) Uani 0.3 1 d . . P B -2
H2C H 0.1170 1.0255 0.2233 0.091 Uiso 0.3 1 calc R U P B -2
C3 C 0.1307(16) 0.811(2) 0.3064(10) 0.080(4) Uani 0.3 1 d . U P B -2
H3C H 0.1371 0.8455 0.3713 0.096 Uiso 0.3 1 calc R U P B -2
C4 C 0.1279(13) 0.645(3) 0.2687(16) 0.103(5) Uani 0.3 1 d . U P B -2
H4C H 0.1334 0.5481 0.3066 0.124 Uiso 0.3 1 calc R U P B -2
C5 C 0.1163(16) 0.647(3) 0.173(2) 0.104(6) Uani 0.3 1 d . U P B -2
H5C H 0.1064 0.5542 0.1318 0.125 Uiso 0.3 1 calc R U P B -2


_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
I2 I3 2.9663(14) . ?
I3 I2 2.9663(14) 2 ?
N1 N5 1.29(3) . ?
N1 N2 1.35(2) . ?
N1 H1N 0.8600 . ?
N2 N3 1.354(19) . ?
N2 H2N 0.8600 . ?
N3 N4 1.41(2) . ?
N3 H3N 0.8600 . ?
N4 N5 1.32(3) . ?
N4 H4N 0.8600 . ?
N5 H5N 0.8600 . ?

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
I2 I3 I2 178.21(2) 2 . ?
N5 N1 N2 113(2) . . ?
N5 N1 H1N 123.7 . . ?
N2 N1 H1N 123.7 . . ?
N3 N2 N1 107.0(18) . . ?
N3 N2 H2N 126.5 . . ?
N1 N2 H2N 126.5 . . ?
N2 N3 N4 103.2(17) . . ?
N2 N3 H3N 128.4 . . ?
N4 N3 H3N 128.4 . . ?
N5 N4 N3 111.0(18) . . ?
N5 N4 H4N 124.5 . . ?
N3 N4 H4N 124.5 . . ?
N1 N5 N4 105(2) . . ?
N1 N5 H5N 127.3 . . ?
N4 N5 H5N 127.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 N1 N2 N3 9(3) . . . . ?
N1 N2 N3 N4 -4(3) . . . . ?
N2 N3 N4 N5 -1(3) . . . . ?
N2 N1 N5 N4 -10(3) . . . . ?
N3 N4 N5 N1 7(3) . . . . ?

_refine_diff_density_max         1.032
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.135

_shelxl_version_number           2013-4

