#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/05/2100552.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_2100552
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         'C5 H6 N2 O Se'
_chemical_formula_sum            'C5 H6 N2 O Se'
_chemical_formula_weight         189.08
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens
'methyl H atoms from delta-F; others placed geometrically'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.157(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.3411(7)
_cell_length_b                   14.756(2)
_cell_length_c                   9.690(2)
_cell_measurement_reflns_used    4328
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.01
_cell_measurement_theta_min      2.63
_cell_volume                     620.71(18)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2004)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2004)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'enCIFer (Allen et al., 2004); PLATON'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD diffractometer'
_diffrn_measurement_method       'fine-slice ω scans'
_diffrn_radiation_monochromator  'silicone (111)'
_diffrn_radiation_source         'Daresbury Laboratory Station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6775
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.027
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6350
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_min         4.01
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.956
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS version 2.10; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.023
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.80
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.803
_refine_ls_hydrogen_treatment    'rigid rotating group; riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.803
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0246
_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)+(0.079P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0742
_reflns_number_gt                1642
_reflns_number_total             1770
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            so5003.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2100552
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N N1 0.2422(3) 0.73923(8) 0.10993(12) 0.0105(2) Uani d . 1
H H1A 0.3737 0.7485 0.1777 0.013 Uiso calc R 1
C C2 0.1605(3) 0.65292(9) 0.08020(14) 0.0104(2) Uani d . 1
Se Se2 0.32333(3) 0.556089(10) 0.173603(14) 0.01181(9) Uani d . 1
N N3 -0.0470(3) 0.64228(8) -0.02297(12) 0.0116(2) Uani d . 1
H H3A -0.1048 0.5866 -0.0428 0.014 Uiso calc R 1
C C4 -0.1767(3) 0.71205(9) -0.10027(15) 0.0119(3) Uani d . 1
O O4 -0.3644(3) 0.69250(9) -0.19136(13) 0.0180(2) Uani d . 1
C C5 -0.0765(3) 0.80120(9) -0.06473(15) 0.0119(2) Uani d . 1
H H5A -0.1540 0.8521 -0.1139 0.014 Uiso calc R 1
C C6 0.1301(3) 0.81340(9) 0.03956(14) 0.0111(2) Uani d . 1
C C7 0.2429(3) 0.90396(9) 0.08536(16) 0.0153(3) Uani d . 1
H H7D 0.2201 0.9475 0.0097 0.023 Uiso calc R 1
H H7A 0.4606 0.8995 0.1116 0.023 Uiso calc R 1
H H7B 0.1223 0.9243 0.1648 0.023 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0136(5) 0.0082(5) 0.0097(5) -0.0003(4) -0.0031(4) -0.0010(4)
C2 0.0119(5) 0.0100(6) 0.0093(6) 0.0011(4) -0.0006(4) 0.0007(4)
Se2 0.01526(13) 0.00869(12) 0.01146(12) 0.00109(4) -0.00368(7) 0.00126(4)
N3 0.0137(5) 0.0089(5) 0.0123(5) -0.0014(4) -0.0043(4) 0.0003(4)
C4 0.0126(6) 0.0115(6) 0.0116(6) 0.0009(5) -0.0018(5) 0.0011(5)
O4 0.0203(5) 0.0170(6) 0.0165(5) -0.0005(4) -0.0106(4) 0.0005(4)
C5 0.0140(6) 0.0100(6) 0.0116(6) 0.0008(5) -0.0032(5) 0.0014(5)
C6 0.0135(6) 0.0089(6) 0.0108(6) 0.0005(4) -0.0005(5) -0.0001(4)
C7 0.0198(7) 0.0093(6) 0.0169(7) -0.0004(5) -0.0052(5) -0.0013(5)
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
C2 N1 C6 123.40(12)
C2 N1 H1A 118.3
C6 N1 H1A 118.3
N1 C2 N3 116.12(12)
N1 C2 Se2 121.90(10)
N3 C2 Se2 121.98(10)
C2 N3 C4 125.41(12)
C2 N3 H3A 117.3
C4 N3 H3A 117.3
O4 C4 N3 118.52(13)
O4 C4 C5 126.04(14)
N3 C4 C5 115.44(13)
C6 C5 C4 120.05(13)
C6 C5 H5A 120.0
C4 C5 H5A 120.0
C5 C6 N1 119.57(12)
C5 C6 C7 123.70(13)
N1 C6 C7 116.72(12)
C6 C7 H7D 109.5
C6 C7 H7A 109.5
H7D C7 H7A 109.5
C6 C7 H7B 109.5
H7D C7 H7B 109.5
H7A C7 H7B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3528(17)
N1 C6 1.3776(17)
N1 H1A 0.8800
C2 N3 1.3531(18)
C2 Se2 1.8322(14)
N3 C4 1.3913(18)
N3 H3A 0.8800
C4 O4 1.2338(18)
C4 C5 1.427(2)
C5 C6 1.361(2)
C5 H5A 0.9500
C6 C7 1.4904(19)
C7 H7D 0.9800
C7 H7A 0.9800
C7 H7B 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20137825
