#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/99/2209930.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_2209930
loop_
_publ_author_name
'Céline Besnard'
'Christian Kloc'
'Theo Siegrist'
'Christer Svensson'
'Krystian Pluta'
_publ_section_title
;
 Diquino[4,3-b;3',4'-e][1,4]thiaselenine
;
_journal_coeditor_code           LH2116
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3203
_journal_page_last               o3205
_journal_paper_doi               10.1107/S1600536806025232
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H10 N2 S1 Se1'
_chemical_formula_moiety         'C18 H10 N2 S1 Se1'
_chemical_formula_sum            'C18 H10 N2 S Se'
_chemical_formula_weight         365.32
_chemical_name_systematic
;
Diquino[4,3-b;3',4'-e][1,4]thiaselenine
;
_space_group_IT_number           31
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac -2'
_symmetry_space_group_name_H-M   'P m n 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           CRYSTALS_ver_12.80
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   23.625(3)
_cell_length_b                   7.3299(9)
_cell_length_c                   4.1297(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     715.14(15)
_computing_cell_refinement       TWINSOLVE
_computing_data_collection       'TWINSOLVE (Rigaku/MSC & Prekat, 2002)'
_computing_data_reduction        TWINSOLVE
_computing_molecular_graphics
;
ORTEP-3 (Burnett & Johnson, 1996) and ATOMS (Dowty, 1994)
;
_computing_publication_material
'CRYSTALS and enCIFer (Allen et al.,  2004)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'mar CCD area-detector'
_diffrn_measurement_method       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.08900
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            3727
_diffrn_reflns_theta_full        32.676
_diffrn_reflns_theta_max         32.676
_diffrn_reflns_theta_min         3.965
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.767
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_description       needle
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.001
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack (1983), with 72 Friedel pairs'
_refine_ls_abs_structure_Flack   0.420(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0408
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         770
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0241
_refine_ls_shift/su_max          0.000169
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w = [1-(Fₒ-Fc)²/36σ²(F)]²/[23.9Tₒ(x)-32.3T₁(x)+11.2T₂(x)]
where Ti are the Chebychev polynomials and x = Fc/Fₘₐₓ
(Prince, 1982; Watkin, 1994)
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0515
_refine_ls_wR_factor_gt          0.0474
_refine_ls_wR_factor_ref         0.0515
_reflns_number_gt                684
_reflns_number_total             770
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2116.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        715.13(15)
_cod_original_sg_symbol_H-M      'P m n 21 '
_cod_original_formula_sum        'C18 H10 N2 S1 Se1'
_cod_database_code               2209930
_cod_database_fobs_code          2209930
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,z
x+1/2,-y,z+1/2
-x+1/2,-y,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_occupancy
N N1 0.6499(2) 0.4209(6) 0.9810(11) 0.0638 Uani 1.0000
C C2 0.6039(2) 0.3715(7) 0.8314(16) 0.0610 Uani 1.0000
C C3 0.55764(16) 0.4888(6) 0.7703(17) 0.0478 Uani 1.0000
C C4 0.56015(18) 0.6649(7) 0.8649(10) 0.0464 Uani 1.0000
C C5 0.6085(2) 0.7276(7) 1.0402(12) 0.0504 Uani 1.0000
C C6 0.6162(2) 0.9055(7) 1.1625(12) 0.0546 Uani 1.0000
C C7 0.6644(2) 0.9538(7) 1.3186(17) 0.0616 Uani 1.0000
C C8 0.7081(2) 0.8289(10) 1.3588(14) 0.0733 Uani 1.0000
C C9 0.70237(19) 0.6534(8) 1.2495(19) 0.0654 Uani 1.0000
C C10 0.6532(2) 0.5966(8) 1.0877(13) 0.0531 Uani 1.0000
Se Se 0.5000 0.83098(10) 0.7698(3) 0.0676 Uani 1.0000
S S 0.5000 0.3993(3) 0.5433(5) 0.0638 Uani 1.0000
H H21 0.6000 0.2560 0.7088 0.0875 Uiso 1.0000
H H61 0.5876 0.9887 1.0846 0.0788 Uiso 1.0000
H H71 0.6681 1.0729 1.3498 0.0888 Uiso 1.0000
H H81 0.7419 0.8635 1.4177 0.1059 Uiso 1.0000
H H91 0.7317 0.5694 1.2281 0.0935 Uiso 1.0000
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 0.058(3) 0.067(3) 0.066(3) 0.016(3) 0.002(3) 0.007(3)
C2 0.065(3) 0.058(3) 0.060(4) 0.009(3) 0.025(4) 0.003(3)
C3 0.047(2) 0.057(3) 0.039(3) 0.001(2) 0.009(4) -0.004(4)
C4 0.035(2) 0.058(3) 0.046(4) 0.009(2) 0.006(2) 0.020(3)
C5 0.043(3) 0.065(3) 0.043(3) 0.005(3) 0.018(3) 0.017(3)
C6 0.045(3) 0.061(4) 0.057(4) -0.003(3) 0.007(3) 0.011(3)
C7 0.052(3) 0.072(3) 0.060(4) -0.004(3) 0.011(4) 0.014(4)
C8 0.046(3) 0.108(5) 0.066(6) -0.009(4) 0.001(3) 0.004(4)
C9 0.046(3) 0.094(4) 0.056(4) 0.013(3) 0.010(5) 0.014(4)
C10 0.045(3) 0.072(4) 0.043(3) 0.011(3) 0.011(3) 0.012(3)
Se 0.0558(4) 0.0635(5) 0.0836(6) 0.0000 0.0000 0.0239(6)
S 0.0731(13) 0.0684(13) 0.0498(12) 0.0000 0.0000 -0.0075(13)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Se -0.0929 2.2259 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 'International Tables Vol C 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
_geom_angle_publ_flag
C2 N1 C10 . 117.6(5) no
N1 C2 C3 . 124.1(5) no
N1 C2 H21 . 123.9 no
C3 C2 H21 . 111.0 no
C2 C3 C4 . 119.8(5) no
C2 C3 S . 117.5(4) no
C4 C3 S . 122.6(4) no
C3 C4 C5 . 119.3(4) no
C3 C4 Se . 121.1(4) no
C5 C4 Se . 119.6(4) no
C4 C5 C6 . 125.6(4) no
C4 C5 C10 . 116.1(5) no
C6 C5 C10 . 118.3(5) no
C5 C6 C7 . 121.3(5) no
C5 C6 H61 . 112.0 no
C7 C6 H61 . 125.5 no
C6 C7 C8 . 120.6(6) no
C6 C7 H71 . 114.1 no
C8 C7 H71 . 124.0 no
C7 C8 C9 . 120.5(5) no
C7 C8 H81 . 121.4 no
C9 C8 H81 . 117.0 no
C8 C9 C10 . 121.1(5) no
C8 C9 H91 . 125.4 no
C10 C9 H91 . 112.0 no
C5 C10 C9 . 118.3(5) no
C5 C10 N1 . 123.0(5) no
C9 C10 N1 . 118.7(5) no
C3 S C3 2_655 99.9(4) yes
C4 Se C4 2_655 96.0(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.303(6) yes
N1 C10 1.363(7) yes
C2 C3 1.413(6) no
C2 H21 0.990 no
C3 C4 1.350(6) yes
C3 S 1.779(5) yes
C4 C5 1.429(7) no
C4 Se 1.912(4) yes
C5 C6 1.410(7) no
C5 C10 1.440(7) no
C6 C7 1.357(7) no
C6 H61 0.964 no
C7 C8 1.388(7) no
C7 H71 0.887 no
C8 C9 1.370(8) no
C8 H81 0.873 no
C9 C10 1.404(7) no
C9 H91 0.932 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127694
