#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:40:09 +0100 (lun 21 de mar de 2016) $
#$Revision: 178476 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/97/4029752.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_4029752
loop_
_publ_author_name
'Meyer, Annemarie'
'Sigmund, Eva'
'Luppertz, Friedhelm'
'Schnakenburg, Gregor'
'Gadaczek, Immanuel'
'Bredow, Thomas'
'Jester, Stefan-S'
'Höger, Sigurd'
_publ_section_title
;
 Syntheses and properties of thienyl-substituted dithienophenazines.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1180
_journal_page_last               1187
_journal_paper_doi               10.3762/bjoc.6.135
_journal_volume                  6
_journal_year                    2010
_chemical_formula_moiety         'C10 H4 O2 S2'
_chemical_formula_sum            'C10 H4 O2 S2'
_chemical_formula_weight         220.27
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.935(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9233(4)
_cell_length_b                   14.8008(8)
_cell_length_c                   6.6258(2)
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      1.00
_cell_volume                     852.88(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7685
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  0.91287
_exptl_absorpt_correction_T_min  0.79308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.429
_exptl_crystal_size_min          0.161
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0068(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0272
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0369P)²+0.0998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                1666
_reflns_number_total             2029
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-6-135-S2.cif
_cod_data_source_block           Greg1219
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/Beilstein/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-Scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/retrospective/Beilstein/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4029752
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_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
S1 S -1.49471(4) -0.89734(3) -0.23340(5) 0.01673(12) Uani 1 1 d .
S2 S -0.96222(4) -0.61493(3) -0.08233(5) 0.01649(12) Uani 1 1 d .
O1 O -1.54678(12) -0.68845(7) -0.25206(15) 0.0192(3) Uani 1 1 d .
O2 O -1.31233(12) -0.56330(7) -0.18320(15) 0.0193(3) Uani 1 1 d .
C1 C -1.34757(18) -0.97329(10) -0.1961(2) 0.0175(3) Uani 1 1 d .
H1 H -1.3624 -1.0369 -0.2026 0.021 Uiso 1 1 calc R
C2 C -1.20535(18) -0.93307(10) -0.1557(2) 0.0156(3) Uani 1 1 d .
H2 H -1.1112 -0.9655 -0.1308 0.019 Uiso 1 1 calc R
C3 C -1.21534(16) -0.83754(9) -0.15533(19) 0.0123(3) Uani 1 1 d .
C4 C -1.36746(17) -0.80857(9) -0.1964(2) 0.0135(3) Uani 1 1 d .
C5 C -1.41305(17) -0.71436(10) -0.2110(2) 0.0137(3) Uani 1 1 d .
C6 C -1.28056(17) -0.64378(10) -0.1734(2) 0.0135(3) Uani 1 1 d .
C7 C -1.12571(16) -0.68020(10) -0.12866(19) 0.0126(3) Uani 1 1 d .
C8 C -1.09130(16) -0.77184(10) -0.12092(18) 0.0120(3) Uani 1 1 d .
C9 C -0.93105(17) -0.78777(11) -0.07770(19) 0.0149(3) Uani 1 1 d .
H9 H -0.8859 -0.8462 -0.0663 0.018 Uiso 1 1 calc R
C10 C -0.84867(17) -0.70882(11) -0.0542(2) 0.0177(3) Uani 1 1 d .
H10 H -0.7395 -0.7066 -0.0253 0.021 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0160(2) 0.0130(2) 0.0205(2) 0.00036(13) 0.00250(14) -0.00359(14)
S2 0.0163(2) 0.0151(2) 0.0181(2) -0.00035(13) 0.00388(14) -0.00478(15)
O1 0.0142(6) 0.0183(6) 0.0249(5) 0.0012(4) 0.0039(4) 0.0022(5)
O2 0.0221(6) 0.0110(6) 0.0241(5) 0.0001(4) 0.0038(4) 0.0013(4)
C1 0.0238(9) 0.0106(7) 0.0173(7) 0.0005(5) 0.0033(6) -0.0013(6)
C2 0.0192(8) 0.0123(7) 0.0148(7) -0.0001(5) 0.0025(5) 0.0019(6)
C3 0.0145(7) 0.0126(7) 0.0096(6) -0.0008(5) 0.0024(5) -0.0003(6)
C4 0.0153(7) 0.0117(7) 0.0133(6) -0.0001(5) 0.0026(5) -0.0020(6)
C5 0.0162(8) 0.0141(7) 0.0108(6) 0.0003(5) 0.0030(5) 0.0011(6)
C6 0.0172(8) 0.0134(7) 0.0104(6) 0.0000(5) 0.0040(5) 0.0003(6)
C7 0.0143(7) 0.0120(7) 0.0115(6) -0.0008(5) 0.0028(5) -0.0029(6)
C8 0.0144(7) 0.0133(7) 0.0086(6) 0.0000(5) 0.0034(5) 0.0002(6)
C9 0.0158(8) 0.0170(8) 0.0120(6) 0.0004(5) 0.0030(5) 0.0022(6)
C10 0.0132(8) 0.0240(9) 0.0157(7) 0.0001(6) 0.0029(5) -0.0005(6)
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C1 S1 C4 91.18(7)
C10 S2 C7 91.22(7)
C2 C1 S1 113.02(11)
C2 C1 H1 123.5
S1 C1 H1 123.5
C1 C2 C3 112.16(13)
C1 C2 H2 123.9
C3 C2 H2 123.9
C4 C3 C2 111.49(13)
C4 C3 C8 120.02(13)
C2 C3 C8 128.49(13)
C3 C4 C5 123.81(13)
C3 C4 S1 112.15(11)
C5 C4 S1 124.02(11)
O1 C5 C4 124.13(14)
O1 C5 C6 119.55(13)
C4 C5 C6 116.32(12)
O2 C6 C7 124.88(13)
O2 C6 C5 119.13(13)
C7 C6 C5 115.99(12)
C8 C7 C6 124.26(13)
C8 C7 S2 111.74(11)
C6 C7 S2 123.99(11)
C7 C8 C9 112.06(13)
C7 C8 C3 119.57(13)
C9 C8 C3 128.37(13)
C10 C9 C8 111.91(14)
C10 C9 H9 124.0
C8 C9 H9 124.0
C9 C10 S2 113.07(12)
C9 C10 H10 123.5
S2 C10 H10 123.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7039(16)
S1 C4 1.7179(14)
S2 C10 1.7054(16)
S2 C7 1.7192(15)
O1 C5 1.2246(18)
O2 C6 1.2228(18)
C1 C2 1.373(2)
C1 H1 0.9500
C2 C3 1.417(2)
C2 H2 0.9500
C3 C4 1.391(2)
C3 C8 1.452(2)
C4 C5 1.450(2)
C5 C6 1.555(2)
C6 C7 1.451(2)
C7 C8 1.389(2)
C8 C9 1.414(2)
C9 C10 1.371(2)
C9 H9 0.9500
C10 H10 0.9500
