#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/33/1503308.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_1503308
loop_
_publ_author_name
'Al-Hashimi, Mohammed'
'Labram, John G.'
'Watkins, Scott'
'Motevalli, Majid'
'Anthopoulos, Thomas D.'
'Heeney, Martin'
_publ_section_title
;
 Synthesis and characterization of fused
 pyrrolo[3,2-d:4,5-d']bisthiazole-containing polymers.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5478
_journal_page_last               5481
_journal_paper_doi               10.1021/ol102344m
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C12 H18 Br2 N2 S2 Si2'
_chemical_formula_sum            'C12 H18 Br2 N2 S2 Si2'
_chemical_formula_weight         470.40
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           86
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      86
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_space_group_name_H-M   'P 42/n :2'
_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                   23.9704(10)
_cell_length_b                   23.9704(10)
_cell_length_c                   6.9043(5)
_cell_measurement_reflns_used    51623
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     3967.1(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & 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  0.1533
_diffrn_reflns_av_sigmaI/netI    0.1408
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            25706
_diffrn_reflns_theta_full        27.64
_diffrn_reflns_theta_max         27.64
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    4.411
_exptl_absorpt_correction_T_max  0.9170
_exptl_absorpt_correction_T_min  0.5210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       0.00035(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         4542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_gt           0.0624
_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)+(0.0360P)²+0.8983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                2356
_reflns_number_total             4542
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol102344m_si_002.cif
_cod_data_source_block           ma-1415
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 42/n'
_cod_database_code               1503308
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -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
C1 C 0.6073(2) 0.5465(2) 0.0822(8) 0.0338(14) Uani 1 1 d .
C2 C 0.5873(2) 0.5984(2) 0.0276(8) 0.0333(14) Uani 1 1 d .
C3 C 0.5229(2) 0.5188(2) 0.0130(8) 0.0287(13) Uani 1 1 d .
C4 C 0.6426(2) 0.6869(2) 0.2761(9) 0.0437(17) Uani 1 1 d .
H4A H 0.6677 0.6581 0.3267 0.066 Uiso 1 1 calc R
H4B H 0.6093 0.6891 0.3580 0.066 Uiso 1 1 calc R
H4C H 0.6619 0.7230 0.2765 0.066 Uiso 1 1 calc R
C5 C 0.5688(2) 0.7186(2) -0.0730(9) 0.0442(17) Uani 1 1 d .
H5A H 0.5846 0.7563 -0.0762 0.066 Uiso 1 1 calc R
H5B H 0.5358 0.7183 0.0109 0.066 Uiso 1 1 calc R
H5C H 0.5581 0.7074 -0.2043 0.066 Uiso 1 1 calc R
C6 C 0.6833(2) 0.6672(3) -0.1414(9) 0.0478(17) Uani 1 1 d .
H6A H 0.7106 0.6402 -0.0928 0.072 Uiso 1 1 calc R
H6B H 0.7004 0.7043 -0.1464 0.072 Uiso 1 1 calc R
H6C H 0.6713 0.6563 -0.2716 0.072 Uiso 1 1 calc R
C7 C 0.4589(2) 0.6096(2) 0.4233(8) 0.0316(14) Uani 1 1 d .
C8 C 0.4829(2) 0.5245(2) 0.4769(8) 0.0331(14) Uani 1 1 d .
C9 C 0.4074(2) 0.5880(2) 0.3869(8) 0.0328(14) Uani 1 1 d .
C10 C 0.3512(3) 0.6413(3) 0.0419(9) 0.059(2) Uani 1 1 d .
H10A H 0.3578 0.6078 -0.0362 0.088 Uiso 1 1 calc R
H10B H 0.3836 0.6661 0.0322 0.088 Uiso 1 1 calc R
H10C H 0.3180 0.6607 -0.0058 0.088 Uiso 1 1 calc R
C11 C 0.3219(3) 0.6825(3) 0.4547(11) 0.060(2) Uani 1 1 d .
H11A H 0.2861 0.6978 0.4116 0.090 Uiso 1 1 calc R
H11B H 0.3510 0.7110 0.4424 0.090 Uiso 1 1 calc R
H11C H 0.3189 0.6708 0.5903 0.090 Uiso 1 1 calc R
C12 C 0.2858(2) 0.5669(2) 0.3248(10) 0.0487(18) Uani 1 1 d .
H12A H 0.2819 0.5564 0.4613 0.073 Uiso 1 1 calc R
H12B H 0.2963 0.5340 0.2488 0.073 Uiso 1 1 calc R
H12C H 0.2503 0.5817 0.2769 0.073 Uiso 1 1 calc R
N1 N 0.57219(19) 0.50215(18) 0.0754(6) 0.0315(11) Uani 1 1 d .
N2 N 0.50171(18) 0.57552(18) 0.4711(6) 0.0313(12) Uani 1 1 d .
Si1 Si 0.62181(7) 0.66881(7) 0.0236(2) 0.0350(4) Uani 1 1 d .
Si2 Si 0.34047(7) 0.62087(7) 0.3013(3) 0.0372(4) Uani 1 1 d .
S1 S 0.51896(6) 0.58865(6) -0.0385(2) 0.0327(4) Uani 1 1 d .
S2 S 0.41304(6) 0.51691(6) 0.4217(2) 0.0329(4) Uani 1 1 d .
Br1 Br 0.68096(2) 0.53432(2) 0.16983(9) 0.0418(2) Uani 1 1 d .
Br2 Br 0.47566(3) 0.68685(2) 0.40733(10) 0.0432(2) 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'
Si Si 0.0817 0.0704 '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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 118.7(5) . .
N1 C1 Br1 118.0(4) . .
C2 C1 Br1 123.2(4) . .
C1 C2 S1 106.3(4) . .
C1 C2 Si1 131.2(4) . .
S1 C2 Si1 122.5(3) . .
N1 C3 C3 122.5(6) . 5_665
N1 C3 S1 114.4(4) . .
C3 C3 S1 123.1(6) 5_665 .
Si1 C4 H4A 109.5 . .
Si1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
Si1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
Si1 C5 H5A 109.5 . .
Si1 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
Si1 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
Si1 C6 H6A 109.5 . .
Si1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
Si1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N2 C7 C9 120.2(5) . .
N2 C7 Br2 116.4(4) . .
C9 C7 Br2 123.5(4) . .
N2 C8 C8 124.3(7) . 5_666
N2 C8 S2 115.3(4) . .
C8 C8 S2 120.4(6) 5_666 .
C7 C9 S2 106.2(4) . .
C7 C9 Si2 132.2(4) . .
S2 C9 Si2 121.5(3) . .
Si2 C10 H10A 109.5 . .
Si2 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
Si2 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
Si2 C11 H11A 109.5 . .
Si2 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
Si2 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
Si2 C12 H12A 109.5 . .
Si2 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
Si2 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C3 N1 C1 109.3(4) . .
C8 N2 C7 108.2(4) . .
C6 Si1 C4 111.4(3) . .
C6 Si1 C5 109.5(3) . .
C4 Si1 C5 111.6(3) . .
C6 Si1 C2 109.8(3) . .
C4 Si1 C2 108.2(3) . .
C5 Si1 C2 106.3(2) . .
C12 Si2 C11 109.5(3) . .
C12 Si2 C10 111.4(3) . .
C11 Si2 C10 111.5(3) . .
C12 Si2 C9 106.5(3) . .
C11 Si2 C9 110.8(3) . .
C10 Si2 C9 107.0(3) . .
C3 S1 C2 91.4(3) . .
C8 S2 C9 90.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.356(7) .
C1 C2 1.385(7) .
C1 Br1 1.890(5) .
C2 S1 1.717(6) .
C2 Si1 1.880(6) .
C3 N1 1.319(6) .
C3 C3 1.432(10) 5_665
C3 S1 1.715(6) .
C4 Si1 1.865(6) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 Si1 1.866(6) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 Si1 1.864(6) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 N2 1.352(7) .
C7 C9 1.362(7) .
C7 Br2 1.897(5) .
C8 N2 1.304(6) .
C8 C8 1.469(11) 5_666
C8 S2 1.727(6) .
C9 S2 1.727(6) .
C9 Si2 1.883(6) .
C10 Si2 1.875(7) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 Si2 1.870(6) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 Si2 1.848(6) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
N1 C1 C2 S1 -0.5(7) .
Br1 C1 C2 S1 -179.6(3) .
N1 C1 C2 Si1 178.1(4) .
Br1 C1 C2 Si1 -0.9(8) .
N2 C7 C9 S2 1.4(7) .
Br2 C7 C9 S2 -179.6(3) .
N2 C7 C9 Si2 -175.1(4) .
Br2 C7 C9 Si2 3.9(8) .
C3 C3 N1 C1 178.9(6) 5_665
S1 C3 N1 C1 0.1(6) .
C2 C1 N1 C3 0.3(7) .
Br1 C1 N1 C3 179.4(4) .
C8 C8 N2 C7 179.7(7) 5_666
S2 C8 N2 C7 0.7(6) .
C9 C7 N2 C8 -1.4(7) .
Br2 C7 N2 C8 179.5(4) .
C1 C2 Si1 C6 60.5(6) .
S1 C2 Si1 C6 -121.0(4) .
C1 C2 Si1 C4 -61.2(6) .
S1 C2 Si1 C4 117.3(4) .
C1 C2 Si1 C5 178.9(5) .
S1 C2 Si1 C5 -2.7(4) .
C7 C9 Si2 C12 -170.9(6) .
S2 C9 Si2 C12 13.0(4) .
C7 C9 Si2 C11 -51.9(6) .
S2 C9 Si2 C11 132.0(4) .
C7 C9 Si2 C10 69.8(6) .
S2 C9 Si2 C10 -106.2(4) .
N1 C3 S1 C2 -0.4(5) .
C3 C3 S1 C2 -179.1(6) 5_665
C1 C2 S1 C3 0.5(4) .
Si1 C2 S1 C3 -178.3(4) .
N2 C8 S2 C9 0.0(5) .
C8 C8 S2 C9 -179.0(6) 5_666
C7 C9 S2 C8 -0.7(4) .
Si2 C9 S2 C8 176.3(4) .
