#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151230.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151230
loop_
_publ_author_name
'Roy, Gouriprasanna'
'Nethaji, Munirathinam'
'Mugesh, G.'
_publ_section_title
;
 Interaction of anti-thyroid drugs with iodine: the isolation of two
 unusual ionic compounds derived from Se-methimazole.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2883
_journal_page_last               2887
_journal_paper_doi               10.1039/b604060h
_journal_volume                  4
_journal_year                    2006
_chemical_formula_moiety         'C8 H12 I2 N4 Se2'
_chemical_formula_sum            'C8 H12 I2 N4 Se2'
_chemical_formula_weight         575.94
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.916(3)
_cell_angle_beta                 82.135(3)
_cell_angle_gamma                78.816(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6979(14)
_cell_length_b                   10.374(2)
_cell_length_c                   12.158(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      1.8
_cell_volume                     771.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7591
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    8.781
_exptl_absorpt_correction_T_max  0.3728
_exptl_absorpt_correction_T_min  0.1781
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0229
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0285P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0576
_reflns_number_gt                2548
_reflns_number_total             2810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b604060h.txt
_cod_data_source_block           compd7_m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'ANALYTICAL' changed to
'analytical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7151230
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_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'
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_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_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) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17242717
