#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/05/2100558.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2100558
loop_
_publ_author_name
'C. D. Antoniadis'
'A. J. Blake'
'S. K. Hadjikakou'
'N. Hadjiliadis'
'P. Hubberstey'
'M. Schröder'
'C. Wilson'
_publ_section_title
;
 Structural characterization of selenium and selenium-diiodine
 analogues of the antithyroid drug 6-n-propyl-2-thiouracil and
 its alkyl derivatives
;
_journal_coeditor_code           SO5003
_journal_date_accepted           2006-03-29
_journal_date_recd_electronic    2006-03-08
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              580
_journal_page_last               591
_journal_paper_category          FA
_journal_paper_doi               10.1107/S0108768106011426
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C24 H26 N8 O4 Se2, 2(H2 O)'
_chemical_formula_sum            'C24 H30 N8 O6 Se2'
_chemical_formula_weight         684.48
_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           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                83.490(3)
_cell_angle_beta                 84.431(3)
_cell_angle_gamma                89.353(3)
_cell_formula_units_Z            1
_cell_length_a                   4.8330(2)
_cell_length_b                   9.7970(5)
_cell_length_c                   14.1796(8)
_cell_measurement_reflns_used    2951
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     663.91(6)
_computing_cell_refinement       'DIRAX (Duisenberg, 1992)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'enCIFer (Allen et al., 2004); PLATON'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Nonius kappaCCD area detector'
_diffrn_measurement_method       'omega and phi'
_diffrn_radiation_source         'FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_sigmaI/netI    0.091
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13298
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.71
_diffrn_reflns_theta_min         3.38
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.842
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         3.35
_refine_diff_density_min         -2.06
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         13281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0840
_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)+(0.098P)²+8.436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.214
_refine_ls_wR_factor_ref         0.221
_reflns_number_gt                12058
_reflns_number_total             13281
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            so5003.cif
_cod_data_source_block           9
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-11-23

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'placed geometrically' was
changed to 'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_database_code               2100558
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_attached_hydrogens
N N1 0.6706(7) 0.1491(4) 0.6086(3) 0.0261(8) Uani d . 1 0
C C2 0.7861(8) 0.1716(4) 0.5228(3) 0.0213(9) Uani d . 1 0
Se Se2 0.64806(8) 0.05982(4) 0.43430(3) 0.01942(13) Uani d . 1 0
N N3 0.9985(7) 0.2698(4) 0.4937(3) 0.0237(8) Uani d . 1 0
C C4 1.0998(8) 0.3449(4) 0.5642(3) 0.0228(8) Uani d . 1 0
O O4 1.2814(7) 0.4333(4) 0.5408(2) 0.0368(8) Uani d . 1 0
C C5 0.9727(8) 0.3122(5) 0.6585(3) 0.0264(9) Uani d . 1 0
H H5A 1.0339 0.3578 0.7084 0.032 Uiso calc R 1 0
C C6 0.7679(8) 0.2185(4) 0.6795(3) 0.0250(9) Uani d . 1 0
C C7 0.6138(9) 0.1823(5) 0.7756(3) 0.0296(10) Uani d . 1 0
H H7A 0.5975 0.0810 0.7879 0.035 Uiso calc R 1 0
H H7B 0.4233 0.2203 0.7747 0.035 Uiso calc R 1 0
C C8 0.7477(10) 0.2343(5) 0.8576(3) 0.0360(11) Uani d . 1 0
H H8A 0.6346 0.2063 0.9177 0.054 Uiso calc R 1 0
H H8B 0.7601 0.3347 0.8473 0.054 Uiso calc R 1 0
H H8C 0.9347 0.1953 0.8605 0.054 Uiso calc R 1 0
N N11 0.9880(7) 0.2203(4) 0.3389(3) 0.0267(8) Uani d . 1 0
C C12 1.1022(9) 0.2925(5) 0.3959(3) 0.0258(9) Uani d . 1 0
N N13 1.3078(7) 0.3826(4) 0.3670(3) 0.0281(8) Uani d . 1 0
H H13A 1.3749 0.4291 0.4093 0.034 Uiso calc R 1 0
C C14 1.4195(9) 0.4051(4) 0.2715(3) 0.0230(9) Uani d . 1 0
O O14 1.6106(6) 0.4878(3) 0.2466(2) 0.0305(7) Uani d . 1 0
C C15 1.2867(9) 0.3226(5) 0.2087(3) 0.0300(10) Uani d . 1 0
H H15A 1.3446 0.3320 0.1424 0.036 Uiso calc R 1 0
C C16 1.0852(9) 0.2345(5) 0.2442(3) 0.0269(10) Uani d . 1 0
C C17 0.9424(9) 0.1403(5) 0.1876(3) 0.0298(10) Uani d . 1 0
H H17A 0.7429 0.1651 0.1898 0.036 Uiso calc R 1 0
H H17B 0.9554 0.0452 0.2188 0.036 Uiso calc R 1 0
C C18 1.0575(13) 0.1433(6) 0.0841(4) 0.0494(15) Uani d . 1 0
H H18A 0.9521 0.0793 0.0529 0.074 Uiso calc R 1 0
H H18B 1.2535 0.1159 0.0807 0.074 Uiso calc R 1 0
H H18C 1.0411 0.2364 0.0517 0.074 Uiso calc R 1 0
O O1 0.7388(8) 0.5170(5) 0.0441(3) 0.0554(11) Uani d . 1 2
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C2 N1 C6 . 119.2(4)
N1 C2 N3 . 123.7(4)
N1 C2 Se2 . 114.7(3)
N3 C2 Se2 . 121.5(3)
C2 Se2 Se2 2_656 88.97(13)
C2 N3 C12 . 119.4(4)
C2 N3 C4 . 118.5(4)
C12 N3 C4 . 122.0(4)
O4 C4 C5 . 124.5(4)
O4 C4 N3 . 120.1(4)
C5 C4 N3 . 115.4(4)
C6 C5 C4 . 122.1(4)
C6 C5 H5A . 119.0
C4 C5 H5A . 119.0
C5 C6 N1 . 121.0(4)
C5 C6 C7 . 125.6(4)
N1 C6 C7 . 113.3(4)
C6 C7 C8 . 114.6(4)
C6 C7 H7A . 108.6
C8 C7 H7A . 108.6
C6 C7 H7B . 108.6
C8 C7 H7B . 108.6
H7A C7 H7B . 107.6
C7 C8 H8A . 109.5
C7 C8 H8B . 109.5
H8A C8 H8B . 109.5
C7 C8 H8C . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
C12 N11 C16 . 118.7(4)
N11 C12 N13 . 123.6(4)
N11 C12 N3 . 116.0(4)
N13 C12 N3 . 120.5(4)
C12 N13 C14 . 122.0(4)
C12 N13 H13A . 119.0
C14 N13 H13A . 119.0
O14 C14 N13 . 120.9(4)
O14 C14 C15 . 125.7(4)
N13 C14 C15 . 113.3(4)
C16 C15 C14 . 120.3(4)
C16 C15 H15A . 119.8
C14 C15 H15A . 119.8
C15 C16 N11 . 122.1(4)
C15 C16 C17 . 125.1(4)
N11 C16 C17 . 112.8(4)
C16 C17 C18 . 115.1(4)
C16 C17 H17A . 108.5
C18 C17 H17A . 108.5
C16 C17 H17B . 108.5
C18 C17 H17B . 108.5
H17A C17 H17B . 107.5
C17 C18 H18A . 109.5
C17 C18 H18B . 109.5
H18A C18 H18B . 109.5
C17 C18 H18C . 109.5
H18A C18 H18C . 109.5
H18B C18 H18C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C2 . 1.284(5)
N1 C6 . 1.396(6)
C2 N3 . 1.414(5)
C2 Se2 . 1.926(4)
Se2 Se2 2_656 2.4328(9)
N3 C12 . 1.423(6)
N3 C4 . 1.433(5)
C4 O4 . 1.235(5)
C4 C5 . 1.420(6)
C5 C6 . 1.346(6)
C5 H5A . 0.9500
C6 C7 . 1.496(6)
C7 C8 . 1.522(7)
C7 H7A . 0.9900
C7 H7B . 0.9900
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
N11 C12 . 1.296(6)
N11 C16 . 1.371(6)
C12 N13 . 1.339(5)
N13 C14 . 1.402(5)
N13 H13A . 0.8800
C14 O14 . 1.234(5)
C14 C15 . 1.464(6)
C15 C16 . 1.331(6)
C15 H15A . 0.9500
C16 C17 . 1.504(6)
C17 C18 . 1.515(7)
C17 H17A . 0.9900
C17 H17B . 0.9900
C18 H18A . 0.9800
C18 H18B . 0.9800
C18 H18C . 0.9800
