#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/87/2208751.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_2208751
loop_
_publ_author_name
'Céline Besnard'
'Christian Kloc'
'Theo Siegrist'
'Christer Svensson'
'Krystian Pluta'
_publ_section_title
;
 Diquino[3,4-b;4',3'-e][1,4]dithiine
;
_journal_coeditor_code           WN2007
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1333
_journal_page_last               o1335
_journal_paper_doi               10.1107/S1600536806007793
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H10 N2 S2'
_chemical_formula_moiety         'C18 H10 N2 S2'
_chemical_formula_sum            'C18 H10 N2 S2'
_chemical_formula_weight         318.42
_chemical_name_systematic
;
Diquino[3,4-b;4',3'-e][1,4]dithiine
;
_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                   23.440(5)
_cell_length_b                   7.5873(15)
_cell_length_c                   3.9960(8)
_cell_measurement_reflns_used    2883
_cell_measurement_temperature    293
_cell_measurement_theta_max      34.420
_cell_measurement_theta_min      3.408
_cell_volume                     710.7(3)
_computing_cell_refinement
;
SAINT  (Siemens, 1995)
;
_computing_data_collection
;
SMART (Siemens, 1995)
;
_computing_data_reduction
;
SAINT
;
_computing_molecular_graphics
;
ORTEPIII (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 0.939
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.90200
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            2883
_diffrn_reflns_theta_full        30.066
_diffrn_reflns_theta_max         34.420
_diffrn_reflns_theta_min         3.408
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details 'Flack (1983), 497 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.11(14)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9641
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1157
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.000138
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w = [1-(Fₒ-Fc)²/36σ²(F)]²/[15.6T₀(x)+20.5T₁(x)+8.37T₂(x)]
where Ti are Chebychev polynomials and x = Fc/Fₘₐₓ
(Prince, 1982; Watkin, 1994)
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0766
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                1157
_reflns_number_total             1157
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2007.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.

'_exptl_absorpt_correction_type' value ' multi-scan ' changed
to 'multi-scan' 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.

'_exptl_absorpt_correction_type' value ' multi-scan '
changed to 'multi-scan' 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_database_code               2208751
_cod_database_fobs_code          2208751
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 N -0.15247(9) 0.4208(3) 0.6446(7) 0.0435 Uani 1.0000
C C2 -0.10638(12) 0.3623(4) 0.5018(8) 0.0408 Uani 1.0000
C C3 -0.05795(10) 0.4654(3) 0.4219(7) 0.0339 Uani 1.0000
C C4 -0.05805(10) 0.6406(3) 0.5055(7) 0.0319 Uani 1.0000
C C5 -0.10680(10) 0.7126(3) 0.6734(7) 0.0323 Uani 1.0000
C C6 -0.11129(11) 0.8900(4) 0.7789(7) 0.0401 Uani 1.0000
C C7 -0.16039(12) 0.9493(4) 0.9317(9) 0.0467 Uani 1.0000
C C8 -0.20638(12) 0.8357(5) 0.9834(9) 0.0513 Uani 1.0000
C C9 -0.20308(11) 0.6637(4) 0.8901(9) 0.0469 Uani 1.0000
C C10 -0.15341(11) 0.5955(4) 0.7340(7) 0.0373 Uani 1.0000
S S2 0.0000 0.77991(13) 0.4020(3) 0.0383 Uani 1.0000
S S1 0.0000 0.36432(15) 0.2145(3) 0.0431 Uani 1.0000
H H21 -0.1056 0.2463 0.3932 0.0591 Uiso 1.0000
H H61 -0.0803 0.9625 0.6864 0.0568 Uiso 1.0000
H H71 -0.1628 1.0667 0.9585 0.0671 Uiso 1.0000
H H81 -0.2392 0.8795 1.0381 0.0733 Uiso 1.0000
H H91 -0.2338 0.5876 0.8783 0.0680 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
N 0.0352(12) 0.0469(13) 0.0485(17) -0.0113(10) -0.0044(11) 0.0064(12)
C2 0.0426(15) 0.0398(15) 0.0400(19) -0.0075(12) -0.0075(13) 0.0032(12)
C3 0.0342(11) 0.0387(12) 0.0288(15) -0.0019(10) -0.0086(11) 0.0043(12)
C4 0.0261(11) 0.0376(13) 0.0318(15) -0.0006(10) -0.0062(10) 0.0102(11)
C5 0.0252(11) 0.0408(14) 0.0309(15) 0.0001(10) -0.0065(10) 0.0099(12)
C6 0.0318(12) 0.0438(15) 0.045(2) 0.0030(11) -0.0082(12) 0.0060(14)
C7 0.0421(14) 0.0516(17) 0.0463(19) 0.0090(12) -0.0072(15) -0.0048(16)
C8 0.0363(14) 0.075(2) 0.043(2) 0.0099(14) 0.0024(13) -0.0014(16)
C9 0.0294(12) 0.0676(19) 0.0436(19) -0.0061(12) -0.0016(13) 0.0051(18)
C10 0.0310(13) 0.0479(15) 0.0332(17) -0.0064(11) -0.0082(12) 0.0077(15)
S2 0.0274(4) 0.0362(4) 0.0512(6) 0.0000 0.0000 0.0185(5)
S1 0.0453(5) 0.0470(5) 0.0371(6) 0.0000 0.0000 -0.0074(5)
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'
S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N C10 . . 117.2(2) no
N C2 C3 . . 125.2(3) no
N C2 H21 . . 121.1 no
C3 C2 H21 . . 112.4 no
C2 C3 C4 . . 118.7(3) no
C2 C3 S1 . . 118.8(2) no
C4 C3 S1 . . 122.5(2) no
C3 C4 C5 . . 119.0(2) no
C3 C4 S2 . . 121.3(2) no
C5 C4 S2 . . 119.6(2) no
C4 C5 C6 . . 124.2(2) no
C4 C5 C10 . . 116.9(2) no
C6 C5 C10 . . 119.0(3) no
C5 C6 C7 . . 120.3(3) no
C5 C6 H61 . . 111.4 no
C7 C6 H61 . . 126.9 no
C6 C7 C8 . . 120.6(3) no
C6 C7 H71 . . 115.4 no
C8 C7 H71 . . 123.0 no
C7 C8 C9 . . 120.5(3) no
C7 C8 H81 . . 119.1 no
C9 C8 H81 . . 119.2 no
C8 C9 C10 . . 121.2(3) no
C8 C9 H91 . . 124.7 no
C10 C9 H91 . . 112.9 no
C5 C10 C9 . . 118.4(3) no
C5 C10 N . . 123.0(3) no
C9 C10 N . . 118.7(2) no
C4 S2 C4 2_555 . 100.34(16) yes
C3 S1 C3 . 2_555 100.52(18) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N C2 1.300(4) yes
N C10 1.373(4) yes
C2 C3 1.416(4) no
C2 H21 0.981 no
C3 C4 1.371(4) yes
C3 S1 1.766(3) yes
C4 C5 1.433(4) no
C4 S2 1.772(3) yes
C5 C6 1.414(4) no
C5 C10 1.429(3) no
C6 C7 1.378(4) no
C6 H61 0.984 no
C7 C8 1.396(4) no
C7 H71 0.899 no
C8 C9 1.359(5) no
C8 H81 0.867 no
C9 C10 1.419(4) no
C9 H91 0.925 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 357950
