#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/51/1505160.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_1505160
loop_
_publ_author_name
'Pang, Hao'
'Skabara, Peter J.'
'Crouch, David J.'
'Duffy, Warren'
'Heeney, Martin'
'McCulloch, Iain'
'Coles, Simon J.'
'Horton, Peter N.'
'Hursthouse, Michael B.'
_publ_section_title
;
 Structural and Electronic Effects of 1,3,4-Thiadiazole Units Incorporated
 into Polythiophene Chains
;
_journal_issue                   18
_journal_name_full               Macromolecules
_journal_page_first              6585
_journal_paper_doi               10.1021/ma071242n
_journal_volume                  40
_journal_year                    2007
_chemical_formula_sum            'C22 H30 N2 S Se2'
_chemical_formula_weight         512.46
_chemical_name_systematic
;
 HS-TDA-HS
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   38.796(3)
_cell_length_b                   12.1462(5)
_cell_length_c                   9.6432(6)
_cell_measurement_reflns_used    2758
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.0
_cell_volume                     4544.1(5)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.675
_diffrn_measured_fraction_theta_max 0.675
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0851
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13370
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        negligible
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    3.356
_exptl_absorpt_correction_T_max  0.9359
_exptl_absorpt_correction_T_min  0.5255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0513
_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)+(0.0472P)²+27.7883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1537
_reflns_number_gt                2183
_reflns_number_total             3530
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ma071242nsi20070604_093751.cif
_cod_data_source_block           HS-TDA-HS
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        4544.1(4)
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               1505160
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
C1 C 0.31912(19) 0.5762(6) 0.3820(7) 0.0209(18) Uani 1 1 d .
C2 C 0.3442(2) 0.5610(7) 0.4903(7) 0.0263(19) Uani 1 1 d .
C3 C 0.3579(2) 0.4657(7) 0.5409(7) 0.0243(19) Uani 1 1 d .
H3 H 0.3511 0.3954 0.5076 0.029 Uiso 1 1 calc R
C4 C 0.3833(2) 0.4789(7) 0.6483(8) 0.0256(19) Uani 1 1 d .
C5 C 0.3885(2) 0.5857(6) 0.6836(7) 0.0251(19) Uani 1 1 d .
H5 H 0.4043 0.6078 0.7535 0.030 Uiso 1 1 calc R
C6 C 0.4016(2) 0.3812(6) 0.7113(8) 0.0281(19) Uani 1 1 d .
H6A H 0.4109 0.3348 0.6358 0.034 Uiso 1 1 calc R
H6B H 0.3846 0.3366 0.7634 0.034 Uiso 1 1 calc R
C7 C 0.4309(2) 0.4126(7) 0.8083(8) 0.031(2) Uani 1 1 d .
H7A H 0.4212 0.4549 0.8870 0.037 Uiso 1 1 calc R
H7B H 0.4469 0.4616 0.7578 0.037 Uiso 1 1 calc R
C8 C 0.45120(19) 0.3147(6) 0.8658(8) 0.031(2) Uani 1 1 d .
H8A H 0.4355 0.2672 0.9203 0.037 Uiso 1 1 calc R
H8B H 0.4602 0.2705 0.7876 0.037 Uiso 1 1 calc R
C9 C 0.4808(2) 0.3502(7) 0.9567(8) 0.033(2) Uani 1 1 d .
H9A H 0.4714 0.3931 1.0352 0.039 Uiso 1 1 calc R
H9B H 0.4958 0.4002 0.9022 0.039 Uiso 1 1 calc R
C10 C 0.5032(2) 0.2588(7) 1.0151(9) 0.037(2) Uani 1 1 d .
H10A H 0.5114 0.2123 0.9377 0.045 Uiso 1 1 calc R
H10B H 0.4889 0.2120 1.0764 0.045 Uiso 1 1 calc R
C11 C 0.5343(2) 0.3004(8) 1.0974(9) 0.044(2) Uani 1 1 d .
H11A H 0.5483 0.3485 1.0384 0.066 Uiso 1 1 calc R
H11B H 0.5482 0.2375 1.1279 0.066 Uiso 1 1 calc R
H11C H 0.5264 0.3418 1.1786 0.066 Uiso 1 1 calc R
C12 C 0.2743(2) 0.5728(6) 0.2117(7) 0.0216(18) Uani 1 1 d .
C13 C 0.2471(2) 0.5522(6) 0.1136(7) 0.0214(18) Uani 1 1 d .
C14 C 0.23115(19) 0.4572(6) 0.0772(7) 0.0223(17) Uani 1 1 d .
H14 H 0.2366 0.3884 0.1185 0.027 Uiso 1 1 calc R
C15 C 0.2053(2) 0.4686(7) -0.0287(8) 0.0252(19) Uani 1 1 d .
C16 C 0.2021(2) 0.5735(6) -0.0754(8) 0.027(2) Uani 1 1 d .
H16 H 0.1867 0.5937 -0.1475 0.033 Uiso 1 1 calc R
C17 C 0.1825(2) 0.3754(7) -0.0782(8) 0.034(2) Uani 1 1 d .
H17A H 0.1965 0.3074 -0.0855 0.041 Uiso 1 1 calc R
H17B H 0.1736 0.3932 -0.1717 0.041 Uiso 1 1 calc R
C18 C 0.1524(3) 0.3548(7) 0.0186(10) 0.050(3) Uani 1 1 d .
H18A H 0.1371 0.2996 -0.0252 0.059 Uiso 1 1 calc R
H18B H 0.1614 0.3218 0.1051 0.059 Uiso 1 1 calc R
C19 C 0.1307(2) 0.4540(7) 0.0572(9) 0.044(3) Uani 1 1 d .
H19A H 0.1454 0.5061 0.1096 0.052 Uiso 1 1 calc R
H19B H 0.1235 0.4914 -0.0293 0.052 Uiso 1 1 calc R
C20 C 0.0997(2) 0.4314(7) 0.1402(11) 0.046(3) Uani 1 1 d .
H20A H 0.1067 0.3899 0.2240 0.056 Uiso 1 1 calc R
H20B H 0.0843 0.3830 0.0854 0.056 Uiso 1 1 calc R
C21 C 0.0792(3) 0.5310(8) 0.1857(11) 0.053(3) Uani 1 1 d .
H21A H 0.0938 0.5765 0.2474 0.063 Uiso 1 1 calc R
H21B H 0.0736 0.5758 0.1030 0.063 Uiso 1 1 calc R
C22 C 0.0462(3) 0.5038(8) 0.2607(13) 0.072(4) Uani 1 1 d .
H22A H 0.0313 0.4597 0.2001 0.108 Uiso 1 1 calc R
H22B H 0.0343 0.5722 0.2858 0.108 Uiso 1 1 calc R
H22C H 0.0515 0.4620 0.3450 0.108 Uiso 1 1 calc R
N1 N 0.31256(18) 0.6743(5) 0.3302(6) 0.0284(16) Uani 1 1 d .
N2 N 0.28737(18) 0.6728(5) 0.2311(6) 0.0271(16) Uani 1 1 d .
S1 S 0.29413(5) 0.47303(16) 0.31156(19) 0.0249(5) Uani 1 1 d .
Se1 Se 0.36198(2) 0.68485(7) 0.58280(8) 0.0295(3) Uani 1 1 d .
Se2 Se 0.23030(2) 0.67360(6) 0.01317(8) 0.0258(3) Uani 1 1 d .
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'
S S 0.1246 0.1234 '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
N1 C1 C2 121.5(7)
N1 C1 S1 113.6(6)
C2 C1 S1 124.9(6)
C3 C2 C1 129.2(7)
C3 C2 Se1 111.5(6)
C1 C2 Se1 119.3(6)
C2 C3 C4 115.5(7)
C5 C4 C3 112.9(7)
C5 C4 C6 125.5(7)
C3 C4 C6 121.5(7)
C4 C5 Se1 113.9(6)
C4 C6 C7 113.6(6)
C6 C7 C8 114.4(7)
C9 C8 C7 112.4(7)
C8 C9 C10 116.2(7)
C9 C10 C11 113.7(7)
N2 C12 C13 122.1(7)
N2 C12 S1 113.0(6)
C13 C12 S1 124.8(6)
C14 C13 C12 130.7(7)
C14 C13 Se2 112.1(6)
C12 C13 Se2 117.1(6)
C13 C14 C15 114.8(7)
C16 C15 C14 112.9(7)
C16 C15 C17 123.0(7)
C14 C15 C17 124.0(7)
C15 C16 Se2 114.3(6)
C15 C17 C18 112.3(7)
C19 C18 C17 116.6(8)
C20 C19 C18 116.0(8)
C19 C20 C21 116.0(8)
C22 C21 C20 114.2(8)
C1 N1 N2 113.0(6)
C12 N2 N1 112.5(6)
C1 S1 C12 87.8(4)
C5 Se1 C2 86.1(3)
C16 Se2 C13 85.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.317(9)
C1 C2 1.440(11)
C1 S1 1.724(8)
C2 C3 1.363(10)
C2 Se1 1.880(8)
C3 C4 1.440(11)
C4 C5 1.355(10)
C4 C6 1.509(11)
C5 Se1 1.860(7)
C6 C7 1.520(11)
C7 C8 1.532(10)
C8 C9 1.509(10)
C9 C10 1.516(11)
C10 C11 1.532(12)
C12 N2 1.331(9)
C12 C13 1.439(10)
C12 S1 1.729(8)
C13 C14 1.355(10)
C13 Se2 1.881(7)
C14 C15 1.438(10)
C15 C16 1.357(10)
C15 C17 1.514(11)
C16 Se2 1.845(8)
C17 C18 1.517(13)
C18 C19 1.516(13)
C19 C20 1.471(12)
C20 C21 1.512(12)
C21 C22 1.508(13)
N1 N2 1.367(9)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30651565 ChemSpider
