Supplementary Material (ESI) for Organic & Biomolecular Chemistry
  This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Govindasamy Mugesh'
_publ_contact_author_address     
;
Department of Inorganic and Physical Chemistry
Indian Institute of Science
Bangalore
560012
INDIA
;

_publ_contact_author_email       MUGESH@IPC.IISC.ERNET.IN

_publ_section_title              
;
Interaction of Anti-Thyroid Drugs with Iodine: The
Isolation of Two Unusual Ionic Compounds Derived from Se-Methimazole
;
loop_
_publ_author_name
'Govindasamy Mugesh'
'Munirathinam Nethaji'
'Gouriprasanna Roy'

data_compd6_m
_database_code_depnum_ccdc_archive 'CCDC 256230'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 I3 N4 Se2'
_chemical_formula_sum            'C8 H11 I3 N4 Se2'
_chemical_formula_weight         701.83

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'
Se Se -0.0929 2.2259 '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   P21/n

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

_cell_length_a                   15.484(6)
_cell_length_b                   12.017(5)
_cell_length_c                   19.604(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.509(6)
_cell_angle_gamma                90.00
_cell_volume                     3515(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.1

_exptl_crystal_description       prism
_exptl_crystal_colour            dark-red
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2512
_exptl_absorpt_coefficient_mu    9.465
_exptl_absorpt_correction_type   ANALYTICAL
_exptl_absorpt_correction_T_min  0.3508
_exptl_absorpt_correction_T_max  0.7033
_exptl_absorpt_process_details   empirical

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 0.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24749
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.06
_reflns_number_total             6220
_reflns_number_gt                4918
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.0441P)^2^+9.0036P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6220
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
I1 I 0.78552(4) 0.88926(5) 0.17446(3) 0.08620(19) Uani 1 1 d . . .
I2 I 0.74523(3) 0.66305(4) 0.12680(2) 0.05801(13) Uani 1 1 d . . .
I3 I 0.69802(4) 0.43704(5) 0.07460(3) 0.07436(16) Uani 1 1 d . . .
I4 I 0.30188(4) 0.89488(6) 0.40208(3) 0.08254(18) Uani 1 1 d . . .
I5 I 0.17943(3) 0.96365(4) 0.26797(3) 0.06555(15) Uani 1 1 d . . .
I6 I 0.06535(4) 1.02477(6) 0.12912(4) 0.0971(2) Uani 1 1 d . . .
Se1 Se 0.37355(5) 1.08549(6) 0.00326(3) 0.05533(18) Uani 1 1 d . . .
Se2 Se 0.25036(5) 1.07261(5) 0.05270(4) 0.05532(18) Uani 1 1 d . . .
Se3 Se 0.61008(5) 0.84123(6) 0.27187(4) 0.05677(18) Uani 1 1 d . . .
Se4 Se 0.49087(5) 0.85157(6) 0.32727(4) 0.05927(19) Uani 1 1 d . . .
N101 N 0.5220(4) 1.0642(4) 0.1270(3) 0.0542(13) Uani 1 1 d . . .
N102 N 0.4850(3) 1.2369(4) 0.1029(3) 0.0486(12) Uani 1 1 d . . .
N103 N 0.3070(4) 0.8893(4) 0.1453(3) 0.0508(13) Uani 1 1 d . . .
H103 H 0.3386 0.9309 0.1783 0.061 Uiso 1 1 calc R . .
N104 N 0.2220(4) 0.8347(5) 0.0446(3) 0.0592(15) Uani 1 1 d . . .
N201 N 0.5082(3) 0.8444(4) 0.1266(3) 0.0483(12) Uani 1 1 d . . .
H201 H 0.5111 0.9156 0.1232 0.058 Uiso 1 1 calc R . .
N202 N 0.5256(3) 0.6764(4) 0.1683(3) 0.0482(12) Uani 1 1 d . . .
N203 N 0.3997(4) 1.0309(4) 0.2432(3) 0.0532(13) Uani 1 1 d . . .
N204 N 0.4792(4) 1.0898(5) 0.3460(3) 0.0532(13) Uani 1 1 d . . .
C1 C 0.4647(4) 1.1310(5) 0.0834(3) 0.0450(14) Uani 1 1 d . . .
C2 C 0.5806(5) 1.1296(6) 0.1755(4) 0.0636(19) Uani 1 1 d . . .
H2 H 0.6280 1.1043 0.2122 0.076 Uiso 1 1 calc R . .
C3 C 0.5576(5) 1.2355(6) 0.1610(4) 0.0625(19) Uani 1 1 d . . .
H3 H 0.5858 1.2973 0.1858 0.075 Uiso 1 1 calc R . .
C4 C 0.4393(5) 1.3371(5) 0.0693(4) 0.0639(19) Uani 1 1 d . . .
H4A H 0.3982 1.3178 0.0248 0.096 Uiso 1 1 calc R . .
H4B H 0.4827 1.3891 0.0613 0.096 Uiso 1 1 calc R . .
H4C H 0.4070 1.3704 0.0996 0.096 Uiso 1 1 calc R . .
C5 C 0.2624(4) 0.9224(5) 0.0820(3) 0.0458(14) Uani 1 1 d . . .
C6 C 0.2947(5) 0.7777(6) 0.1497(4) 0.0618(18) Uani 1 1 d . . .
H6 H 0.3190 0.7330 0.1888 0.074 Uiso 1 1 calc R . .
C7 C 0.2417(5) 0.7440(6) 0.0881(5) 0.068(2) Uani 1 1 d . . .
H7 H 0.2216 0.6717 0.0766 0.081 Uiso 1 1 calc R . .
C8 C 0.1630(7) 0.8361(8) -0.0273(5) 0.108(4) Uani 1 1 d . . .
H8A H 0.1126 0.8835 -0.0290 0.162 Uiso 1 1 calc R . .
H8B H 0.1423 0.7620 -0.0409 0.162 Uiso 1 1 calc R . .
H8C H 0.1953 0.8638 -0.0593 0.162 Uiso 1 1 calc R . .
C9 C 0.5432(4) 0.7846(5) 0.1836(3) 0.0460(14) Uani 1 1 d . . .
C10 C 0.4667(4) 0.7739(6) 0.0744(3) 0.0540(16) Uani 1 1 d . . .
H10 H 0.4359 0.7948 0.0286 0.065 Uiso 1 1 calc R . .
C11 C 0.4768(5) 0.6695(6) 0.0987(4) 0.0563(17) Uani 1 1 d . . .
H11 H 0.4551 0.6051 0.0736 0.068 Uiso 1 1 calc R . .
C12 C 0.5575(5) 0.5825(6) 0.2153(4) 0.0654(19) Uani 1 1 d . . .
H12A H 0.6045 0.6068 0.2551 0.098 Uiso 1 1 calc R . .
H12B H 0.5800 0.5258 0.1901 0.098 Uiso 1 1 calc R . .
H12C H 0.5089 0.5531 0.2316 0.098 Uiso 1 1 calc R . .
C13 C 0.4556(4) 1.0000(5) 0.3039(3) 0.0472(14) Uani 1 1 d . . .
C14 C 0.3871(5) 1.1431(6) 0.2462(4) 0.0622(18) Uani 1 1 d . . .
H14 H 0.3506 1.1867 0.2109 0.075 Uiso 1 1 calc R . .
C15 C 0.4370(5) 1.1793(6) 0.3094(4) 0.0625(18) Uani 1 1 d . . .
H15 H 0.4418 1.2526 0.3253 0.075 Uiso 1 1 calc R . .
C16 C 0.5345(6) 1.0903(8) 0.4194(4) 0.077(2) Uani 1 1 d . . .
H16A H 0.5008 1.0601 0.4496 0.116 Uiso 1 1 calc R . .
H16B H 0.5519 1.1653 0.4336 0.116 Uiso 1 1 calc R . .
H16C H 0.5872 1.0459 0.4231 0.116 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 0.0888(4) 0.0848(4) 0.0650(3) -0.0076(3) -0.0143(3) -0.0169(3)
I2 0.0437(2) 0.0783(3) 0.0478(3) 0.0050(2) 0.00491(19) 0.0011(2)
I3 0.0781(4) 0.0680(3) 0.0687(3) 0.0027(2) 0.0053(3) 0.0001(3)
I4 0.0730(4) 0.1024(4) 0.0730(4) -0.0039(3) 0.0210(3) -0.0113(3)
I5 0.0614(3) 0.0589(3) 0.0836(4) -0.0093(2) 0.0320(3) -0.0037(2)
I6 0.0766(4) 0.1203(5) 0.0975(5) 0.0242(4) 0.0287(3) 0.0297(4)
Se1 0.0630(4) 0.0572(4) 0.0391(3) 0.0004(3) 0.0022(3) -0.0107(3)
Se2 0.0505(4) 0.0484(4) 0.0585(4) 0.0037(3) -0.0003(3) 0.0056(3)
Se3 0.0506(4) 0.0602(4) 0.0510(4) -0.0024(3) -0.0011(3) 0.0090(3)
Se4 0.0724(5) 0.0579(4) 0.0447(4) 0.0093(3) 0.0107(3) 0.0086(3)
N101 0.056(3) 0.051(3) 0.049(3) 0.004(2) 0.002(3) -0.004(3)
N102 0.055(3) 0.040(3) 0.048(3) -0.001(2) 0.008(3) -0.003(2)
N103 0.054(3) 0.046(3) 0.051(3) -0.004(2) 0.012(3) -0.002(2)
N104 0.048(3) 0.051(3) 0.070(4) -0.010(3) 0.001(3) -0.004(3)
N201 0.047(3) 0.043(3) 0.050(3) 0.000(2) 0.005(2) 0.003(2)
N202 0.047(3) 0.045(3) 0.055(3) 0.003(2) 0.018(3) 0.002(2)
N203 0.063(3) 0.048(3) 0.045(3) 0.001(2) 0.007(3) 0.006(3)
N204 0.051(3) 0.064(3) 0.044(3) -0.008(3) 0.012(3) -0.005(3)
C1 0.051(4) 0.046(3) 0.036(3) -0.001(3) 0.007(3) -0.005(3)
C2 0.061(4) 0.060(4) 0.058(4) 0.008(3) -0.004(3) -0.005(3)
C3 0.062(4) 0.063(4) 0.053(4) -0.006(3) -0.002(3) -0.017(4)
C4 0.076(5) 0.043(4) 0.072(5) 0.001(3) 0.018(4) 0.004(3)
C5 0.039(3) 0.045(3) 0.051(4) -0.005(3) 0.007(3) -0.001(3)
C6 0.066(5) 0.048(4) 0.076(5) 0.006(4) 0.027(4) 0.006(3)
C7 0.057(4) 0.044(4) 0.104(6) -0.007(4) 0.027(4) -0.004(3)
C8 0.108(8) 0.085(6) 0.093(7) -0.032(5) -0.038(6) 0.002(5)
C9 0.044(3) 0.045(3) 0.048(3) 0.000(3) 0.010(3) 0.007(3)
C10 0.053(4) 0.062(4) 0.044(4) 0.001(3) 0.007(3) 0.005(3)
C11 0.056(4) 0.050(4) 0.063(5) -0.011(3) 0.017(3) -0.001(3)
C12 0.074(5) 0.049(4) 0.075(5) 0.016(4) 0.022(4) 0.009(3)
C13 0.048(4) 0.056(4) 0.039(3) -0.001(3) 0.013(3) 0.000(3)
C14 0.069(5) 0.057(4) 0.059(4) 0.001(3) 0.014(4) 0.010(3)
C15 0.076(5) 0.052(4) 0.063(5) -0.006(3) 0.025(4) 0.000(4)
C16 0.076(5) 0.104(6) 0.049(4) -0.018(4) 0.012(4) -0.015(5)

_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
I1 I2 2.8879(12) . ?
I2 I3 2.9254(12) . ?
I4 I5 2.9196(12) . ?
I5 I6 2.9152(12) . ?
Se1 C1 1.891(6) . ?
Se1 Se2 2.3644(13) . ?
Se2 C5 1.888(6) . ?
Se3 C9 1.890(6) . ?
Se3 Se4 2.3821(13) . ?
Se4 C13 1.886(7) . ?
N101 C1 1.325(8) . ?
N101 C2 1.372(9) . ?
N102 C1 1.342(8) . ?
N102 C3 1.371(8) . ?
N102 C4 1.461(8) . ?
N103 C5 1.310(8) . ?
N103 C6 1.361(8) . ?
N103 H103 0.8600 . ?
N104 C5 1.340(8) . ?
N104 C7 1.366(9) . ?
N104 C8 1.461(10) . ?
N201 C9 1.317(8) . ?
N201 C10 1.351(8) . ?
N201 H201 0.8600 . ?
N202 C9 1.345(8) . ?
N202 C11 1.374(9) . ?
N202 C12 1.457(8) . ?
N203 C13 1.323(8) . ?
N203 C14 1.366(9) . ?
N204 C13 1.348(8) . ?
N204 C15 1.359(9) . ?
N204 C16 1.465(9) . ?
C2 C3 1.331(10) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 C7 1.329(10) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 C11 1.337(9) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.345(10) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
I1 I2 I3 177.76(2) . . ?
I6 I5 I4 176.06(3) . . ?
C1 Se1 Se2 100.55(19) . . ?
C5 Se2 Se1 99.33(19) . . ?
C9 Se3 Se4 97.75(19) . . ?
C13 Se4 Se3 98.52(19) . . ?
C1 N101 C2 107.8(5) . . ?
C1 N102 C3 107.5(5) . . ?
C1 N102 C4 127.3(5) . . ?
C3 N102 C4 125.2(6) . . ?
C5 N103 C6 108.2(6) . . ?
C5 N103 H103 125.9 . . ?
C6 N103 H103 125.9 . . ?
C5 N104 C7 107.0(6) . . ?
C5 N104 C8 126.8(6) . . ?
C7 N104 C8 126.1(7) . . ?
C9 N201 C10 107.8(5) . . ?
C9 N201 H201 126.1 . . ?
C10 N201 H201 126.1 . . ?
C9 N202 C11 107.7(5) . . ?
C9 N202 C12 126.4(6) . . ?
C11 N202 C12 125.7(6) . . ?
C13 N203 C14 107.7(6) . . ?
C13 N204 C15 107.3(6) . . ?
C13 N204 C16 126.6(6) . . ?
C15 N204 C16 125.9(6) . . ?
N101 C1 N102 109.0(5) . . ?
N101 C1 Se1 125.7(5) . . ?
N102 C1 Se1 125.2(5) . . ?
C3 C2 N101 108.0(6) . . ?
C3 C2 H2 126.0 . . ?
N101 C2 H2 126.0 . . ?
C2 C3 N102 107.6(6) . . ?
C2 C3 H3 126.2 . . ?
N102 C3 H3 126.2 . . ?
N102 C4 H4A 109.5 . . ?
N102 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N102 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N103 C5 N104 109.2(6) . . ?
N103 C5 Se2 124.3(5) . . ?
N104 C5 Se2 126.3(5) . . ?
C7 C6 N103 107.8(7) . . ?
C7 C6 H6 126.1 . . ?
N103 C6 H6 126.1 . . ?
C6 C7 N104 107.7(6) . . ?
C6 C7 H7 126.1 . . ?
N104 C7 H7 126.1 . . ?
N104 C8 H8A 109.5 . . ?
N104 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N104 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N201 C9 N202 109.0(5) . . ?
N201 C9 Se3 125.5(5) . . ?
N202 C9 Se3 125.5(5) . . ?
C11 C10 N201 109.4(6) . . ?
C11 C10 H10 125.3 . . ?
N201 C10 H10 125.3 . . ?
C10 C11 N202 106.1(6) . . ?
C10 C11 H11 126.9 . . ?
N202 C11 H11 126.9 . . ?
N202 C12 H12A 109.5 . . ?
N202 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N202 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N203 C13 N204 109.3(6) . . ?
N203 C13 Se4 124.1(5) . . ?
N204 C13 Se4 126.5(5) . . ?
C15 C14 N203 107.8(6) . . ?
C15 C14 H14 126.1 . . ?
N203 C14 H14 126.1 . . ?
C14 C15 N204 107.8(6) . . ?
C14 C15 H15 126.1 . . ?
N204 C15 H15 126.1 . . ?
N204 C16 H16A 109.5 . . ?
N204 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N204 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C1 Se1 Se2 C5 -90.1(3) . . . . ?
C9 Se3 Se4 C13 -92.7(3) . . . . ?
C2 N101 C1 N102 -0.1(8) . . . . ?
C2 N101 C1 Se1 176.4(5) . . . . ?
C3 N102 C1 N101 -0.2(7) . . . . ?
C4 N102 C1 N101 179.8(6) . . . . ?
C3 N102 C1 Se1 -176.7(5) . . . . ?
C4 N102 C1 Se1 3.3(10) . . . . ?
Se2 Se1 C1 N101 94.6(6) . . . . ?
Se2 Se1 C1 N102 -89.5(5) . . . . ?
C1 N101 C2 C3 0.4(9) . . . . ?
N101 C2 C3 N102 -0.5(9) . . . . ?
C1 N102 C3 C2 0.4(8) . . . . ?
C4 N102 C3 C2 -179.5(7) . . . . ?
C6 N103 C5 N104 -0.7(7) . . . . ?
C6 N103 C5 Se2 174.5(5) . . . . ?
C7 N104 C5 N103 1.3(7) . . . . ?
C8 N104 C5 N103 177.4(8) . . . . ?
C7 N104 C5 Se2 -173.8(5) . . . . ?
C8 N104 C5 Se2 2.3(11) . . . . ?
Se1 Se2 C5 N103 92.7(5) . . . . ?
Se1 Se2 C5 N104 -92.9(6) . . . . ?
C5 N103 C6 C7 -0.2(8) . . . . ?
N103 C6 C7 N104 1.0(8) . . . . ?
C5 N104 C7 C6 -1.4(8) . . . . ?
C8 N104 C7 C6 -177.5(8) . . . . ?
C10 N201 C9 N202 0.7(7) . . . . ?
C10 N201 C9 Se3 179.2(5) . . . . ?
C11 N202 C9 N201 -0.5(7) . . . . ?
C12 N202 C9 N201 175.8(6) . . . . ?
C11 N202 C9 Se3 -179.0(5) . . . . ?
C12 N202 C9 Se3 -2.8(9) . . . . ?
Se4 Se3 C9 N201 96.1(5) . . . . ?
Se4 Se3 C9 N202 -85.6(5) . . . . ?
C9 N201 C10 C11 -0.7(7) . . . . ?
N201 C10 C11 N202 0.4(8) . . . . ?
C9 N202 C11 C10 0.1(7) . . . . ?
C12 N202 C11 C10 -176.2(6) . . . . ?
C14 N203 C13 N204 0.0(8) . . . . ?
C14 N203 C13 Se4 177.6(5) . . . . ?
C15 N204 C13 N203 -0.7(7) . . . . ?
C16 N204 C13 N203 175.1(6) . . . . ?
C15 N204 C13 Se4 -178.1(5) . . . . ?
C16 N204 C13 Se4 -2.4(10) . . . . ?
Se3 Se4 C13 N203 84.5(6) . . . . ?
Se3 Se4 C13 N204 -98.4(5) . . . . ?
C13 N203 C14 C15 0.6(8) . . . . ?
N203 C14 C15 N204 -1.0(8) . . . . ?
C13 N204 C15 C14 1.1(8) . . . . ?
C16 N204 C15 C14 -174.8(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.435
_refine_diff_density_min         -1.203
_refine_diff_density_rms         0.126

# Attachment 'structure7_m.cif'

data_compd7_m
_database_code_depnum_ccdc_archive 'CCDC 293611'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 I2 N4 Se2'
_chemical_formula_sum            'C8 H12 I2 N4 Se2'
_chemical_formula_weight         575.94

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'
Se Se -0.0929 2.2259 '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                   6.6979(14)
_cell_length_b                   10.374(2)
_cell_length_c                   12.158(3)
_cell_angle_alpha                68.916(3)
_cell_angle_beta                 82.135(3)
_cell_angle_gamma                78.816(3)
_cell_volume                     771.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      25.4

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    8.781
_exptl_absorpt_correction_type   ANALYTICAL
_exptl_absorpt_correction_T_min  0.1781
_exptl_absorpt_correction_T_max  0.3728
_exptl_absorpt_process_details   empirical

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 0.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7591
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2810
_reflns_number_gt                2548
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.0285P)^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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2810
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0576
_refine_ls_wR_factor_gt          0.0564
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
I1 I 0.25171(4) -0.21272(2) 0.00509(2) 0.04143(9) Uani 1 1 d . . .
I2 I 0.12076(4) -0.27400(2) 0.50821(2) 0.04100(9) Uani 1 1 d . . .
Se1 Se 0.77242(6) -0.12855(4) 0.17534(3) 0.03725(11) Uani 1 1 d . . .
Se2 Se 0.78399(6) -0.34817(4) 0.33273(3) 0.03822(11) Uani 1 1 d . . .
N11 N 0.3413(5) -0.0251(3) 0.1792(3) 0.0420(7) Uani 1 1 d . . .
H11 H 0.3215 -0.0642 0.1309 0.050 Uiso 1 1 calc R . .
N12 N 0.4864(5) 0.0353(3) 0.2951(3) 0.0375(7) Uani 1 1 d . . .
N21 N 0.4191(5) -0.4537(3) 0.3326(3) 0.0388(7) Uani 1 1 d . . .
H21 H 0.3566 -0.4216 0.3863 0.047 Uiso 1 1 calc R . .
N22 N 0.6446(4) -0.4960(3) 0.2020(2) 0.0357(7) Uani 1 1 d . . .
C1 C 0.5188(6) -0.0384(3) 0.2233(3) 0.0349(8) Uani 1 1 d . . .
C2 C 0.1976(6) 0.0587(4) 0.2218(4) 0.0529(11) Uani 1 1 d . . .
H2 H 0.0618 0.0855 0.2037 0.064 Uiso 1 1 calc R . .
C3 C 0.2883(6) 0.0964(4) 0.2956(4) 0.0477(10) Uani 1 1 d . . .
H3 H 0.2265 0.1535 0.3386 0.057 Uiso 1 1 calc R . .
C4 C 0.6439(7) 0.0576(4) 0.3559(4) 0.0545(11) Uani 1 1 d . . .
H4A H 0.7154 -0.0312 0.4018 0.082 Uiso 1 1 calc R . .
H4B H 0.5812 0.1085 0.4071 0.082 Uiso 1 1 calc R . .
H4C H 0.7382 0.1101 0.2986 0.082 Uiso 1 1 calc R . .
C5 C 0.6037(5) -0.4306(3) 0.2811(3) 0.0339(8) Uani 1 1 d . . .
C6 C 0.3442(6) -0.5359(4) 0.2874(3) 0.0441(9) Uani 1 1 d . . .
H6 H 0.2190 -0.5675 0.3092 0.053 Uiso 1 1 calc R . .
C7 C 0.4851(6) -0.5624(4) 0.2056(3) 0.0422(9) Uani 1 1 d . . .
H7 H 0.4761 -0.6159 0.1599 0.051 Uiso 1 1 calc R . .
C8 C 0.8298(7) -0.4956(5) 0.1233(4) 0.0642(13) Uani 1 1 d . . .
H8A H 0.8363 -0.4022 0.0694 0.096 Uiso 1 1 calc R . .
H8B H 0.8279 -0.5561 0.0795 0.096 Uiso 1 1 calc R . .
H8C H 0.9469 -0.5283 0.1691 0.096 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 0.04858(17) 0.03735(14) 0.03996(15) -0.01477(11) -0.00034(12) -0.00953(11)
I2 0.03945(16) 0.04231(14) 0.04309(16) -0.01918(11) -0.00015(11) -0.00389(11)
Se1 0.0320(2) 0.0370(2) 0.0450(2) -0.01935(16) 0.00530(16) -0.00609(15)
Se2 0.0363(2) 0.0383(2) 0.0430(2) -0.01706(16) -0.00256(17) -0.00698(16)
N11 0.0357(18) 0.0471(18) 0.0502(19) -0.0228(15) -0.0023(15) -0.0112(15)
N12 0.0385(18) 0.0355(15) 0.0391(17) -0.0144(13) 0.0023(14) -0.0077(13)
N21 0.0312(17) 0.0391(16) 0.0437(18) -0.0164(14) 0.0064(14) -0.0018(13)
N22 0.0345(17) 0.0379(15) 0.0356(16) -0.0148(13) 0.0032(13) -0.0079(13)
C1 0.035(2) 0.0335(17) 0.0361(19) -0.0108(15) 0.0024(16) -0.0102(15)
C2 0.032(2) 0.054(2) 0.072(3) -0.021(2) -0.001(2) -0.0064(18)
C3 0.038(2) 0.044(2) 0.059(3) -0.0221(19) 0.0110(19) -0.0041(18)
C4 0.052(3) 0.071(3) 0.053(3) -0.034(2) -0.009(2) -0.010(2)
C5 0.032(2) 0.0313(17) 0.0360(19) -0.0101(14) 0.0002(15) -0.0037(14)
C6 0.032(2) 0.041(2) 0.056(2) -0.0131(18) 0.0011(18) -0.0118(16)
C7 0.043(2) 0.0381(19) 0.052(2) -0.0205(17) -0.0025(19) -0.0132(17)
C8 0.053(3) 0.089(3) 0.070(3) -0.053(3) 0.032(2) -0.030(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
Se1 C1 1.899(4) . ?
Se1 Se2 2.3862(6) . ?
Se2 C5 1.892(3) . ?
N11 C1 1.333(5) . ?
N11 C2 1.346(5) . ?
N11 H11 0.8600 . ?
N12 C1 1.326(4) . ?
N12 C3 1.355(5) . ?
N12 C4 1.463(5) . ?
N21 C5 1.332(4) . ?
N21 C6 1.363(5) . ?
N21 H21 0.8600 . ?
N22 C5 1.336(4) . ?
N22 C7 1.367(5) . ?
N22 C8 1.458(5) . ?
C2 C3 1.349(5) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 C7 1.339(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
C1 Se1 Se2 98.32(10) . . ?
C5 Se2 Se1 99.92(10) . . ?
C1 N11 C2 109.7(3) . . ?
C1 N11 H11 125.1 . . ?
C2 N11 H11 125.1 . . ?
C1 N12 C3 109.4(3) . . ?
C1 N12 C4 125.2(3) . . ?
C3 N12 C4 125.2(3) . . ?
C5 N21 C6 109.7(3) . . ?
C5 N21 H21 125.1 . . ?
C6 N21 H21 125.1 . . ?
C5 N22 C7 109.3(3) . . ?
C5 N22 C8 125.4(3) . . ?
C7 N22 C8 125.3(3) . . ?
N12 C1 N11 107.0(3) . . ?
N12 C1 Se1 127.6(3) . . ?
N11 C1 Se1 125.0(3) . . ?
N11 C2 C3 106.9(4) . . ?
N11 C2 H2 126.6 . . ?
C3 C2 H2 126.6 . . ?
C2 C3 N12 107.1(3) . . ?
C2 C3 H3 126.5 . . ?
N12 C3 H3 126.5 . . ?
N12 C4 H4A 109.5 . . ?
N12 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N12 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N21 C5 N22 106.8(3) . . ?
N21 C5 Se2 124.6(3) . . ?
N22 C5 Se2 127.8(3) . . ?
C7 C6 N21 107.0(3) . . ?
C7 C6 H6 126.5 . . ?
N21 C6 H6 126.5 . . ?
C6 C7 N22 107.1(3) . . ?
C6 C7 H7 126.4 . . ?
N22 C7 H7 126.4 . . ?
N22 C8 H8A 109.5 . . ?
N22 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N22 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
C1 Se1 Se2 C5 78.54(16) . . . . ?
C3 N12 C1 N11 -0.6(4) . . . . ?
C4 N12 C1 N11 -175.4(3) . . . . ?
C3 N12 C1 Se1 172.6(3) . . . . ?
C4 N12 C1 Se1 -2.3(5) . . . . ?
C2 N11 C1 N12 1.0(4) . . . . ?
C2 N11 C1 Se1 -172.4(3) . . . . ?
Se2 Se1 C1 N12 88.6(3) . . . . ?
Se2 Se1 C1 N11 -99.4(3) . . . . ?
C1 N11 C2 C3 -1.0(5) . . . . ?
N11 C2 C3 N12 0.6(4) . . . . ?
C1 N12 C3 C2 0.0(4) . . . . ?
C4 N12 C3 C2 174.8(4) . . . . ?
C6 N21 C5 N22 1.0(4) . . . . ?
C6 N21 C5 Se2 -169.3(2) . . . . ?
C7 N22 C5 N21 -1.0(4) . . . . ?
C8 N22 C5 N21 178.5(3) . . . . ?
C7 N22 C5 Se2 168.9(3) . . . . ?
C8 N22 C5 Se2 -11.5(5) . . . . ?
Se1 Se2 C5 N21 -110.1(3) . . . . ?
Se1 Se2 C5 N22 81.7(3) . . . . ?
C5 N21 C6 C7 -0.6(4) . . . . ?
N21 C6 C7 N22 0.0(4) . . . . ?
C5 N22 C7 C6 0.6(4) . . . . ?
C8 N22 C7 C6 -178.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.108