#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/75/2207513.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_2207513
loop_
_publ_author_name
'Tai-Hsiang Huang'
'Wha-Tzong Whang'
'Yuh-Sheng Wen'
'Jiann T. Lin'
_publ_section_title
2,8-Bis(3-phenylquinoxalin-2-yl)-5λ⁶-dibenzo[b,d]thiophene-5,5-dione
_journal_coeditor_code           CV6605
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4126
_journal_page_last               o4127
_journal_paper_doi               10.1107/S1600536805037116
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C40 H24 N4 O2 S'
_chemical_formula_moiety         'C40 H24 N4 O2 S'
_chemical_formula_sum            'C40 H24 N4 O2 S'
_chemical_formula_weight         624.69
_chemical_name_systematic
;
2,8-Bis(3-phenylquinoxalin-2-yl)-5λ⁶-dibenzo[b,d]thiophene-5,5-dione
;
_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           SHELXL-97
_cell_angle_alpha                107.719(2)
_cell_angle_beta                 103.656(2)
_cell_angle_gamma                108.751(2)
_cell_formula_units_Z            2
_cell_length_a                   10.7261(3)
_cell_length_b                   12.0606(4)
_cell_length_c                   13.4213(4)
_cell_measurement_reflns_used    2322
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.79
_cell_measurement_theta_min      2.81
_cell_volume                     1454.81(9)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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    0.0917
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10660
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.8731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.376
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.817
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         5107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.817
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0372
_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)+(0.0197P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0660
_reflns_number_gt                3245
_reflns_number_total             5107
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6605.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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        1454.81(8)
_cod_database_code               2207513
_cod_database_fobs_code          2207513
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
S 0.65043(5) 0.27357(5) 0.12649(4) 0.01926(14) Uani d . 1 S
O1 0.76356(12) 0.24307(12) 0.17244(10) 0.0241(4) Uani d . 1 O
O2 0.68013(13) 0.40782(12) 0.16261(10) 0.0253(4) Uani d . 1 O
N15 -0.10700(16) -0.13455(15) 0.16983(13) 0.0203(4) Uani d . 1 N
N20 0.03999(16) -0.17217(15) 0.02488(13) 0.0202(4) Uani d . 1 N
N31 0.27533(15) -0.04102(15) -0.56219(13) 0.0193(4) Uani d . 1 N
N36 0.27356(16) -0.14886(15) -0.40301(13) 0.0198(4) Uani d . 1 N
C1 0.49144(19) 0.18760(17) 0.13926(15) 0.0158(5) Uani d . 1 C
C2 0.4673(2) 0.19486(18) 0.23710(16) 0.0196(5) Uani d . 1 C
H2 0.5388 0.2501 0.3071 0.023 Uiso calc R 1 H
C3 0.33453(19) 0.11822(18) 0.22892(16) 0.0176(5) Uani d . 1 C
H3 0.3167 0.1226 0.2942 0.021 Uiso calc R 1 H
C4 0.22654(19) 0.03402(18) 0.12383(15) 0.0161(5) Uani d . 1 C
C5 0.25356(19) 0.02761(18) 0.02635(16) 0.0167(5) Uani d . 1 C
H5 0.1826 -0.0284 -0.0437 0.020 Uiso calc R 1 H
C6 0.38588(19) 0.10446(18) 0.03327(15) 0.0159(5) Uani d . 1 C
C7 0.57698(19) 0.19306(18) -0.02262(15) 0.0166(5) Uani d . 1 C
C8 0.6462(2) 0.20939(18) -0.09500(15) 0.0194(5) Uani d . 1 C
H8 0.7415 0.2653 -0.0682 0.023 Uiso calc R 1 H
C9 0.56781(19) 0.13899(18) -0.20963(15) 0.0188(5) Uani d . 1 C
H9 0.6111 0.1495 -0.2606 0.023 Uiso calc R 1 H
C10 0.42590(19) 0.05305(18) -0.24989(15) 0.0166(5) Uani d . 1 C
C11 0.3600(2) 0.03607(17) -0.17472(15) 0.0175(5) Uani d . 1 C
H11 0.2660 -0.0229 -0.2010 0.021 Uiso calc R 1 H
C12 0.43587(19) 0.10797(18) -0.05996(15) 0.0159(5) Uani d . 1 C
C13 0.08693(19) -0.06046(18) 0.10997(15) 0.0160(5) Uani d . 1 C
C14 0.0091(2) -0.03983(18) 0.18279(15) 0.0177(5) Uani d . 1 C
C16 -0.2768(2) -0.3543(2) 0.06555(17) 0.0255(5) Uani d . 1 C
H16 -0.3252 -0.3442 0.1143 0.031 Uiso calc R 1 H
C17 -0.3249(2) -0.4702(2) -0.02315(16) 0.0261(5) Uani d . 1 C
H17 -0.4062 -0.5386 -0.0342 0.031 Uiso calc R 1 H
C18 -0.2533(2) -0.4876(2) -0.09801(16) 0.0264(5) Uani d . 1 C
H18 -0.2880 -0.5667 -0.1585 0.032 Uiso calc R 1 H
C19 -0.1342(2) -0.38923(19) -0.08193(16) 0.0240(5) Uani d . 1 C
H19 -0.0863 -0.4012 -0.1308 0.029 Uiso calc R 1 H
C21 -0.1550(2) -0.25146(19) 0.08262(16) 0.0192(5) Uani d . 1 C
C22 -0.0825(2) -0.26914(19) 0.00808(16) 0.0188(5) Uani d . 1 C
C23 0.05205(19) 0.08657(18) 0.27509(16) 0.0185(5) Uani d . 1 C
C24 0.04512(19) 0.0919(2) 0.37891(16) 0.0239(5) Uani d . 1 C
H24 0.0113 0.0164 0.3891 0.029 Uiso calc R 1 H
C25 0.0885(2) 0.2094(2) 0.46672(18) 0.0295(6) Uani d . 1 C
H25 0.0849 0.2127 0.5361 0.035 Uiso calc R 1 H
C26 0.1370(2) 0.3215(2) 0.45185(18) 0.0315(6) Uani d . 1 C
H26 0.1681 0.4003 0.5117 0.038 Uiso calc R 1 H
C27 0.1393(2) 0.3170(2) 0.34830(18) 0.0300(6) Uani d . 1 C
H27 0.1700 0.3925 0.3378 0.036 Uiso calc R 1 H
C28 0.09613(19) 0.20017(19) 0.26054(17) 0.0239(5) Uani d . 1 C
H28 0.0965 0.1974 0.1906 0.029 Uiso calc R 1 H
C29 0.34346(19) -0.02434(18) -0.37276(15) 0.0153(5) Uani d . 1 C
C30 0.34116(19) 0.03147(18) -0.45263(16) 0.0165(5) Uani d . 1 C
C32 0.12020(19) -0.25091(19) -0.71055(16) 0.0218(5) Uani d . 1 C
H32 0.1236 -0.2174 -0.7643 0.026 Uiso calc R 1 H
C33 0.0377(2) -0.3768(2) -0.74290(17) 0.0252(5) Uani d . 1 C
H33 -0.0176 -0.4284 -0.8186 0.030 Uiso calc R 1 H
C34 0.0342(2) -0.43102(19) -0.66333(17) 0.0251(5) Uani d . 1 C
H34 -0.0231 -0.5178 -0.6872 0.030 Uiso calc R 1 H
C35 0.11427(19) -0.35711(18) -0.55194(16) 0.0218(5) Uani d . 1 C
H35 0.1143 -0.3938 -0.5002 0.026 Uiso calc R 1 H
C37 0.20146(19) -0.16994(19) -0.59525(16) 0.0186(5) Uani d . 1 C
C38 0.19752(19) -0.22385(19) -0.51556(16) 0.0191(5) Uani d . 1 C
C39 0.40417(19) 0.17258(18) -0.41860(15) 0.0179(5) Uani d . 1 C
C40 0.3745(2) 0.25289(19) -0.33674(15) 0.0218(5) Uani d . 1 C
H40 0.3203 0.2184 -0.2997 0.026 Uiso calc R 1 H
C41 0.4253(2) 0.3833(2) -0.31057(16) 0.0249(5) Uani d . 1 C
H41 0.4044 0.4360 -0.2567 0.030 Uiso calc R 1 H
C42 0.5071(2) 0.4352(2) -0.36455(16) 0.0271(5) Uani d . 1 C
H42 0.5418 0.5230 -0.3464 0.032 Uiso calc R 1 H
C43 0.5377(2) 0.35760(19) -0.44530(16) 0.0238(5) Uani d . 1 C
H43 0.5928 0.3928 -0.4815 0.029 Uiso calc R 1 H
C44 0.48566(19) 0.22658(19) -0.47212(15) 0.0204(5) Uani d . 1 C
H44 0.5058 0.1743 -0.5269 0.024 Uiso calc R 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 S O2 117.01(8) y
O1 S C1 112.40(9) ?
O2 S C1 110.57(8) ?
O1 S C7 110.72(8) y
O2 S C7 110.94(9) ?
C1 S C7 92.60(9) ?
C14 N15 C21 118.26(17) ?
C13 N20 C22 118.56(17) ?
C30 N31 C37 117.41(17) ?
C29 N36 C38 117.08(17) ?
C2 C1 C6 121.64(18) ?
C2 C1 S 127.57(15) ?
C6 C1 S 110.78(14) y
C1 C2 C3 118.62(18) ?
C1 C2 H2 120.7 ?
C3 C2 H2 120.7 ?
C2 C3 C4 121.04(18) ?
C2 C3 H3 119.5 ?
C4 C3 H3 119.5 ?
C5 C4 C3 119.36(18) ?
C5 C4 C13 117.04(16) ?
C3 C4 C13 123.28(17) ?
C6 C5 C4 120.22(17) ?
C6 C5 H5 119.9 ?
C4 C5 H5 119.9 ?
C5 C6 C1 119.12(17) ?
C5 C6 C12 128.05(17) ?
C1 C6 C12 112.79(17) y
C8 C7 C12 122.64(17) ?
C8 C7 S 126.47(15) ?
C12 C7 S 110.89(14) y
C7 C8 C9 117.29(17) ?
C7 C8 H8 121.4 ?
C9 C8 H8 121.4 ?
C8 C9 C10 121.48(18) ?
C8 C9 H9 119.3 ?
C10 C9 H9 119.3 ?
C11 C10 C9 119.90(17) ?
C11 C10 C29 118.88(17) ?
C9 C10 C29 121.20(17) ?
C12 C11 C10 119.33(17) ?
C12 C11 H11 120.3 ?
C10 C11 H11 120.3 ?
C7 C12 C11 119.31(17) ?
C7 C12 C6 112.89(16) y
C11 C12 C6 127.79(17) ?
N20 C13 C14 120.87(17) ?
N20 C13 C4 113.17(17) ?
C14 C13 C4 125.89(17) ?
N15 C14 C13 121.05(17) ?
N15 C14 C23 115.88(17) ?
C13 C14 C23 123.07(17) ?
C17 C16 C21 119.78(19) ?
C17 C16 H16 120.1 ?
C21 C16 H16 120.1 ?
C16 C17 C18 121.02(19) ?
C16 C17 H17 119.5 ?
C18 C17 H17 119.5 ?
C19 C18 C17 119.9(2) ?
C19 C18 H18 120.0 ?
C17 C18 H18 120.0 ?
C18 C19 C22 120.36(19) ?
C18 C19 H19 119.8 ?
C22 C19 H19 119.8 ?
N15 C21 C16 120.41(18) ?
N15 C21 C22 120.37(17) ?
C16 C21 C22 119.22(18) ?
N20 C22 C19 119.53(18) ?
N20 C22 C21 120.76(18) ?
C19 C22 C21 119.67(18) ?
C28 C23 C24 118.77(18) ?
C28 C23 C14 121.84(18) ?
C24 C23 C14 119.37(18) ?
C25 C24 C23 120.0(2) ?
C25 C24 H24 120.0 ?
C23 C24 H24 120.0 ?
C26 C25 C24 120.3(2) ?
C26 C25 H25 119.8 ?
C24 C25 H25 119.8 ?
C25 C26 C27 120.1(2) ?
C25 C26 H26 119.9 ?
C27 C26 H26 119.9 ?
C28 C27 C26 119.8(2) ?
C28 C27 H27 120.1 ?
C26 C27 H27 120.1 ?
C27 C28 C23 120.92(19) ?
C27 C28 H28 119.5 ?
C23 C28 H28 119.5 ?
N36 C29 C30 122.23(17) ?
N36 C29 C10 115.19(17) ?
C30 C29 C10 122.58(17) ?
N31 C30 C29 121.18(18) ?
N31 C30 C39 116.14(17) ?
C29 C30 C39 122.59(17) ?
C33 C32 C37 120.3(2) ?
C33 C32 H32 119.9 ?
C37 C32 H32 119.9 ?
C32 C33 C34 120.98(19) ?
C32 C33 H33 119.5 ?
C34 C33 H33 119.5 ?
C35 C34 C33 120.49(19) ?
C35 C34 H34 119.8 ?
C33 C34 H34 119.8 ?
C34 C35 C38 119.5(2) ?
C34 C35 H35 120.3 ?
C38 C35 H35 120.3 ?
N31 C37 C38 121.13(17) ?
N31 C37 C32 119.99(18) ?
C38 C37 C32 118.77(18) ?
N36 C38 C37 120.74(18) ?
N36 C38 C35 119.35(18) ?
C37 C38 C35 119.91(17) ?
C44 C39 C40 118.60(18) ?
C44 C39 C30 120.81(17) ?
C40 C39 C30 120.46(18) ?
C41 C40 C39 120.45(19) ?
C41 C40 H40 119.8 ?
C39 C40 H40 119.8 ?
C42 C41 C40 119.95(19) ?
C42 C41 H41 120.0 ?
C40 C41 H41 120.0 ?
C43 C42 C41 120.4(2) ?
C43 C42 H42 119.8 ?
C41 C42 H42 119.8 ?
C42 C43 C44 119.54(19) ?
C42 C43 H43 120.2 ?
C44 C43 H43 120.2 ?
C39 C44 C43 121.04(18) ?
C39 C44 H44 119.5 ?
C43 C44 H44 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S O1 1.4353(13) y
S O2 1.4407(13) y
S C1 1.7669(19) y
S C7 1.7747(19) y
N15 C14 1.322(2) y
N15 C21 1.366(2) y
N20 C13 1.315(2) y
N20 C22 1.362(2) y
N31 C30 1.325(2) y
N31 C37 1.365(2) y
N36 C29 1.320(2) y
N36 C38 1.370(2) y
C1 C2 1.380(2) ?
C1 C6 1.397(2) ?
C2 C3 1.383(2) ?
C2 H2 0.9300 ?
C3 C4 1.401(2) ?
C3 H3 0.9300 ?
C4 C5 1.391(2) ?
C4 C13 1.489(2) y
C5 C6 1.386(2) ?
C5 H5 0.9300 ?
C6 C12 1.480(3) ?
C7 C8 1.377(2) ?
C7 C12 1.388(2) ?
C8 C9 1.389(2) ?
C8 H8 0.9300 ?
C9 C10 1.393(2) ?
C9 H9 0.9300 ?
C10 C11 1.389(2) ?
C10 C29 1.489(2) y
C11 C12 1.389(2) ?
C11 H11 0.9300 ?
C13 C14 1.444(2) ?
C14 C23 1.483(3) y
C16 C17 1.368(3) ?
C16 C21 1.393(2) ?
C16 H16 0.9300 ?
C17 C18 1.408(3) ?
C17 H17 0.9300 ?
C18 C19 1.351(3) ?
C18 H18 0.9300 ?
C19 C22 1.402(3) ?
C19 H19 0.9300 ?
C21 C22 1.413(2) ?
C23 C28 1.389(3) ?
C23 C24 1.396(3) ?
C24 C25 1.384(3) ?
C24 H24 0.9300 ?
C25 C26 1.378(3) ?
C25 H25 0.9300 ?
C26 C27 1.381(3) ?
C26 H26 0.9300 ?
C27 C28 1.378(3) ?
C27 H27 0.9300 ?
C28 H28 0.9300 ?
C29 C30 1.428(3) ?
C30 C39 1.484(3) y
C32 C33 1.353(3) ?
C32 C37 1.416(2) ?
C32 H32 0.9300 ?
C33 C34 1.413(3) ?
C33 H33 0.9300 ?
C34 C35 1.363(2) ?
C34 H34 0.9300 ?
C35 C38 1.419(3) ?
C35 H35 0.9300 ?
C37 C38 1.413(3) ?
C39 C44 1.385(2) ?
C39 C40 1.401(2) ?
C40 C41 1.384(3) ?
C40 H40 0.9300 ?
C41 C42 1.382(3) ?
C41 H41 0.9300 ?
C42 C43 1.381(3) ?
C42 H42 0.9300 ?
C43 C44 1.389(3) ?
C43 H43 0.9300 ?
C44 H44 0.9300 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126901
