#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/33/4113320.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_4113320
loop_
_publ_author_name
'Christopher A. Thomas'
'Kyukwan Zong'
'Khalil A. Abboud'
'Peter J. Steel'
'John R. Reynolds'
_publ_section_title
;
 Donor-Mediated Band Gap Reduction in a Homologous Series of Conjugated
 Polymers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16440
_journal_page_last               16450
_journal_paper_doi               10.1021/ja048637w
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C13 H9 N O2 S2'
_chemical_formula_sum            'C13 H9 N O2 S2'
_chemical_formula_weight         275.33
_chemical_name_common            Th-CNV-EDOT
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9420(10)
_cell_length_b                   10.082(2)
_cell_length_c                   23.879(3)
_cell_measurement_reflns_used    61
_cell_measurement_temperature    148(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      7
_cell_volume                     1189.7(4)
_computing_cell_refinement       xscans
_computing_data_collection       xscans
_computing_data_reduction        xscans
_computing_molecular_graphics    xp
_computing_publication_material  xcif
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      148(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Siemens P4s'
_diffrn_measurement_method       omega
_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  0.0391
_diffrn_reflns_av_sigmaI/netI    0.1100
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            2134
_diffrn_reflns_theta_full        23.98
_diffrn_reflns_theta_max         23.98
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        19
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    0.980
_refine_ls_goodness_of_fit_ref   0.757
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.757
_refine_ls_restrained_S_gt       0.980
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0394
_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)+(0.0280P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                1032
_reflns_number_total             1872
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja048637wsi20040413_011707_3.cif
_cod_data_source_block           3jr12
_cod_database_code               4113320
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_calc_flag
_atom_site_refinement_flags
S1 S 0.3516(2) 0.10930(9) 0.04267(4) 0.0345(3) Uani 1 d .
C2 C 0.2708(6) 0.2202(3) 0.09570(12) 0.0224(8) Uani 1 d .
C3 C 0.4267(6) 0.3322(3) 0.09021(13) 0.0216(8) Uani 1 d .
C4 C 0.6038(6) 0.3292(3) 0.04384(12) 0.0208(8) Uani 1 d .
C5 C 0.5862(7) 0.2144(3) 0.01522(14) 0.0326(9) Uani 1 d .
H5 H 0.6925 0.1942 -0.01665 0.039 Uiso 1 calc R
O1 O 0.7707(4) 0.4317(2) 0.03071(9) 0.0300(6) Uani 1 d .
C6 C 0.7937(7) 0.5280(3) 0.07457(14) 0.0335(9) Uani 1 d .
H6A H 0.8667 0.6115 0.05900 0.040 Uiso 1 calc R
H6B H 0.9230 0.4954 0.10330 0.040 Uiso 1 calc R
C7 C 0.5286(7) 0.5550(3) 0.10129(14) 0.0329(10) Uani 1 d .
H7A H 0.5529 0.6236 0.13059 0.040 Uiso 1 calc R
H7B H 0.4013 0.5904 0.07279 0.040 Uiso 1 calc R
O2 O 0.4139(4) 0.4375(2) 0.12610(9) 0.0271(6) Uani 1 d .
C8 C 0.0674(6) 0.2002(3) 0.13659(12) 0.0235(8) Uani 1 d .
H8 H 0.0326 0.2755 0.15930 0.028 Uiso 1 calc R
C9 C -0.0843(7) 0.0937(3) 0.14885(13) 0.0237(8) Uani 1 d .
C10 C -0.0438(7) -0.0322(4) 0.12112(14) 0.0293(9) Uani 1 d .
N1 N -0.0111(7) -0.1355(3) 0.10225(13) 0.0476(10) Uani 1 d .
S2 S -0.3185(2) 0.21383(10) 0.24147(4) 0.0394(3) Uani 1 d .
C11 C -0.2879(7) 0.0880(3) 0.19342(12) 0.0239(8) Uani 1 d .
C12 C -0.4678(6) -0.0113(3) 0.20429(14) 0.0283(9) Uani 1 d .
H12 H -0.4833 -0.0894 0.18228 0.034 Uiso 1 calc R
C13 C -0.6283(7) 0.0146(4) 0.25170(14) 0.0348(10) Uani 1 d .
H13 H -0.7632 -0.0442 0.26519 0.042 Uiso 1 calc R
C14 C -0.5683(7) 0.1321(4) 0.27563(15) 0.0394(10) Uani 1 d .
H14 H -0.6559 0.1655 0.30798 0.047 Uiso 1 calc R
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'
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
C5 S1 C2 92.3(2)
C3 C2 C8 125.7(3)
C3 C2 S1 109.1(2)
C8 C2 S1 125.2(3)
O2 C3 C2 123.4(3)
O2 C3 C4 122.6(3)
C2 C3 C4 114.1(3)
C5 C4 O1 125.0(3)
C5 C4 C3 112.1(3)
O1 C4 C3 122.9(3)
C4 C5 S1 112.4(3)
C4 O1 C6 113.0(2)
O1 C6 C7 111.9(3)
O2 C7 C6 112.1(3)
C3 O2 C7 111.1(2)
C9 C8 C2 131.5(3)
C8 C9 C10 121.5(3)
C8 C9 C11 125.1(3)
C10 C9 C11 113.3(3)
N1 C10 C9 175.9(4)
C14 S2 C11 91.8(2)
C12 C11 C9 128.0(3)
C12 C11 S2 110.7(2)
C9 C11 S2 121.2(3)
C11 C12 C13 112.8(3)
C14 C13 C12 112.3(3)
C13 C14 S2 112.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.705(3)
S1 C2 1.738(3)
C2 C3 1.373(4)
C2 C8 1.421(4)
C3 O2 1.367(3)
C3 C4 1.417(4)
C4 C5 1.347(4)
C4 O1 1.360(4)
O1 C6 1.432(4)
C6 C7 1.487(4)
C7 O2 1.443(4)
C8 C9 1.343(4)
C9 C10 1.446(5)
C9 C11 1.471(4)
C10 N1 1.147(4)
S2 C14 1.698(4)
S2 C11 1.718(3)
C11 C12 1.365(4)
C12 C13 1.411(4)
C13 C14 1.348(5)
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
C5 S1 C2 C3 -0.2(3)
C5 S1 C2 C8 177.3(3)
C8 C2 C3 O2 3.5(5)
S1 C2 C3 O2 -179.0(3)
C8 C2 C3 C4 -176.6(3)
S1 C2 C3 C4 0.9(4)
O2 C3 C4 C5 178.5(3)
C2 C3 C4 C5 -1.4(4)
O2 C3 C4 O1 -1.4(5)
C2 C3 C4 O1 178.7(3)
O1 C4 C5 S1 -178.9(2)
C3 C4 C5 S1 1.3(4)
C2 S1 C5 C4 -0.6(3)
C5 C4 O1 C6 -166.7(3)
C3 C4 O1 C6 13.1(4)
C4 O1 C6 C7 -41.1(4)
O1 C6 C7 O2 60.3(4)
C2 C3 O2 C7 -161.4(3)
C4 C3 O2 C7 18.7(4)
C6 C7 O2 C3 -46.7(4)
C3 C2 C8 C9 -174.7(3)
S1 C2 C8 C9 8.2(5)
C2 C8 C9 C10 4.5(6)
C2 C8 C9 C11 179.4(3)
C8 C9 C10 N1 129.5(56)
C11 C9 C10 N1 -45.9(58)
C8 C9 C11 C12 172.5(3)
C10 C9 C11 C12 -12.2(5)
C8 C9 C11 S2 -9.2(5)
C10 C9 C11 S2 166.0(2)
C14 S2 C11 C12 0.4(3)
C14 S2 C11 C9 -178.1(3)
C9 C11 C12 C13 178.0(3)
S2 C11 C12 C13 -0.4(4)
C11 C12 C13 C14 0.2(5)
C12 C13 C14 S2 0.2(4)
C11 S2 C14 C13 -0.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660489
