#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/15/4501567.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_4501567
loop_
_publ_author_name
'Tavazzi, Silvia'
'Miozzo, Luciano'
'Silvestri, Leonardo'
'Mora, Stefano'
'Spearman, Peter'
'Moret, Massimo'
'Rizzato, Silvia'
'Braga, Daniele'
'Diagne Diaw, Abdou Karim'
'Gningue-Sall, Diariatou'
'Aaron, Jean-Jacques'
'Yassar, Abderrahim'
_publ_section_title
;
 Crystal Structure and Optical Properties of N-Pyrrole End-Capped
 Thiophene/Phenyl Co-Oligomer: Strong H-type Excitonic Coupling and
 Emission Self-Waveguiding
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2342
_journal_paper_doi               10.1021/cg100113h
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C28 H20 N2 S2'
_chemical_formula_sum            'C28 H20 N2 S2'
_chemical_formula_weight         448.58
_chemical_melting_point          >260&#x00B0;C
_chemical_name_common            pyrrole-phenyl-thiophene
_chemical_name_systematic
;
 1,1'-(bithiophen-5,5''-diyldibenzene-4,1-diyl)bis(1H-pyrrole)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.760(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.7692(10)
_cell_length_b                   7.4252(12)
_cell_length_c                   24.716(4)
_cell_measurement_reflns_used    3787
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.47
_cell_volume                     1058.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 (version 1.08)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al 2002)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13585
_diffrn_reflns_theta_full        29.49
_diffrn_reflns_theta_max         29.49
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.9229
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flat prismatic'
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.46(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5407
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0432
_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)+(0.0525P)²+0.0173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                4257
_reflns_number_total             5407
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100113h_si_001.cif
_cod_data_source_block           compound5
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4501567
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
S1 S 0.92346(9) 0.18021(9) 0.38093(2) 0.04414(15) Uani 1 1 d .
S2 S 0.60478(9) 0.07702(9) 0.53601(2) 0.04458(15) Uani 1 1 d .
C1 C 0.7272(4) 0.1230(3) 0.42948(9) 0.0391(6) Uani 1 1 d .
C2 C 0.5344(4) 0.0482(3) 0.40594(10) 0.0449(6) Uani 1 1 d .
H2 H 0.4081 0.0098 0.4254 0.054 Uiso 1 1 calc R
C3 C 0.5442(4) 0.0346(3) 0.34945(9) 0.0451(6) Uani 1 1 d .
H3 H 0.4246 -0.0134 0.3279 0.054 Uiso 1 1 calc R
C4 C 0.7456(3) 0.0985(3) 0.32900(9) 0.0385(5) Uani 1 1 d .
C5 C 0.8186(4) 0.1003(3) 0.27259(9) 0.0382(5) Uani 1 1 d .
C6 C 1.0240(4) 0.1823(4) 0.25738(9) 0.0446(5) Uani 1 1 d .
H6 H 1.1159 0.2411 0.2834 0.054 Uiso 1 1 calc R
C7 C 1.0937(4) 0.1781(4) 0.20475(9) 0.0470(5) Uani 1 1 d .
H7 H 1.2316 0.2339 0.1957 0.056 Uiso 1 1 calc R
C8 C 0.9612(4) 0.0920(3) 0.16506(9) 0.0428(5) Uani 1 1 d .
C9 C 0.7545(4) 0.0111(3) 0.17954(10) 0.0492(6) Uani 1 1 d .
H9 H 0.6618 -0.0463 0.1534 0.059 Uiso 1 1 calc R
C10 C 0.6873(4) 0.0155(3) 0.23214(9) 0.0459(6) Uani 1 1 d .
H10 H 0.5492 -0.0402 0.2411 0.055 Uiso 1 1 calc R
C11 C 1.2297(5) 0.1619(5) 0.09121(11) 0.0694(8) Uani 1 1 d .
H11 H 1.3346 0.2328 0.1110 0.083 Uiso 1 1 calc R
C12 C 1.2458(6) 0.1190(5) 0.03897(12) 0.0811(10) Uani 1 1 d .
H12 H 1.3625 0.1548 0.0162 0.097 Uiso 1 1 calc R
C13 C 1.0563(7) 0.0111(6) 0.02483(12) 0.0877(11) Uani 1 1 d .
H13 H 1.0232 -0.0378 -0.0092 0.105 Uiso 1 1 calc R
C14 C 0.9294(6) -0.0099(5) 0.06922(11) 0.0774(9) Uani 1 1 d .
H14 H 0.7939 -0.0771 0.0712 0.093 Uiso 1 1 calc R
C15 C 0.7889(4) 0.1474(3) 0.48633(9) 0.0399(5) Uani 1 1 d .
C16 C 0.9898(4) 0.2116(3) 0.50923(10) 0.0463(6) Uani 1 1 d .
H16 H 1.1112 0.2557 0.4892 0.056 Uiso 1 1 calc R
C17 C 0.9964(4) 0.2051(3) 0.56580(9) 0.0463(6) Uani 1 1 d .
H17 H 1.1228 0.2447 0.5868 0.056 Uiso 1 1 calc R
C18 C 0.8009(4) 0.1354(3) 0.58738(9) 0.0377(5) Uani 1 1 d .
C19 C 0.7453(3) 0.1160(3) 0.64424(9) 0.0357(5) Uani 1 1 d .
C20 C 0.8905(4) 0.1862(4) 0.68515(9) 0.0445(5) Uani 1 1 d .
H20 H 1.0282 0.2415 0.6758 0.053 Uiso 1 1 calc R
C21 C 0.8369(4) 0.1764(4) 0.73871(9) 0.0448(5) Uani 1 1 d .
H21 H 0.9389 0.2229 0.7650 0.054 Uiso 1 1 calc R
C22 C 0.6305(4) 0.0969(3) 0.75381(9) 0.0379(5) Uani 1 1 d .
C23 C 0.4855(4) 0.0252(3) 0.71389(10) 0.0465(6) Uani 1 1 d .
H23 H 0.3477 -0.0297 0.7234 0.056 Uiso 1 1 calc R
C24 C 0.5419(4) 0.0339(3) 0.66027(9) 0.0440(6) Uani 1 1 d .
H24 H 0.4419 -0.0163 0.6342 0.053 Uiso 1 1 calc R
C25 C 0.6956(5) 0.1636(4) 0.85197(9) 0.0571(6) Uani 1 1 d .
H25 H 0.8373 0.2227 0.8500 0.069 Uiso 1 1 calc R
C26 C 0.5776(6) 0.1346(4) 0.89772(11) 0.0669(8) Uani 1 1 d .
H26 H 0.6234 0.1707 0.9325 0.080 Uiso 1 1 calc R
C27 C 0.3754(5) 0.0410(4) 0.88347(11) 0.0666(8) Uani 1 1 d .
H27 H 0.2626 0.0029 0.9070 0.080 Uiso 1 1 calc R
C28 C 0.3731(4) 0.0156(4) 0.82932(10) 0.0549(7) Uani 1 1 d .
H28 H 0.2575 -0.0432 0.8091 0.066 Uiso 1 1 calc R
N1 N 1.0336(3) 0.0846(3) 0.11087(7) 0.0513(5) Uani 1 1 d .
N2 N 0.5710(3) 0.0914(3) 0.80907(7) 0.0432(4) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 S1 C1 92.44(11)
C15 S2 C18 92.48(10)
C2 C1 C15 129.8(2)
C2 C1 S1 110.40(18)
C15 C1 S1 119.68(15)
C1 C2 C3 113.5(2)
C4 C3 C2 113.8(2)
C3 C4 C5 128.8(2)
C3 C4 S1 109.84(17)
C5 C4 S1 121.39(16)
C10 C5 C6 117.0(2)
C10 C5 C4 120.9(2)
C6 C5 C4 122.05(19)
C7 C6 C5 121.4(2)
C6 C7 C8 120.7(2)
C7 C8 C9 118.5(2)
C7 C8 N1 121.1(2)
C9 C8 N1 120.4(2)
C10 C9 C8 120.3(2)
C9 C10 C5 122.1(2)
C12 C11 N1 109.0(3)
C11 C12 C13 107.6(3)
C14 C13 C12 107.7(3)
C13 C14 N1 108.4(3)
C16 C15 C1 128.9(2)
C16 C15 S2 110.16(17)
C1 C15 S2 120.81(15)
C15 C16 C17 113.6(2)
C18 C17 C16 114.0(2)
C17 C18 C19 128.5(2)
C17 C18 S2 109.75(16)
C19 C18 S2 121.64(16)
C24 C19 C20 116.8(2)
C24 C19 C18 122.03(19)
C20 C19 C18 121.14(19)
C21 C20 C19 122.2(2)
C20 C21 C22 120.2(2)
C23 C22 C21 118.5(2)
C23 C22 N2 121.1(2)
C21 C22 N2 120.4(2)
C24 C23 C22 120.9(2)
C23 C24 C19 121.4(2)
C26 C25 N2 108.5(2)
C25 C26 C27 107.9(3)
C28 C27 C26 107.6(3)
C27 C28 N2 108.6(2)
C14 N1 C11 107.2(2)
C14 N1 C8 126.5(2)
C11 N1 C8 126.1(2)
C25 N2 C28 107.4(2)
C25 N2 C22 126.6(2)
C28 N2 C22 126.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.728(2)
S1 C1 1.728(2)
S2 C15 1.729(2)
S2 C18 1.730(2)
C1 C2 1.358(3)
C1 C15 1.450(3)
C2 C3 1.403(3)
C3 C4 1.366(3)
C4 C5 1.469(3)
C5 C10 1.387(3)
C5 C6 1.394(3)
C6 C7 1.374(3)
C7 C8 1.382(3)
C8 C9 1.392(3)
C8 N1 1.416(3)
C9 C10 1.368(3)
C11 C12 1.336(4)
C11 N1 1.371(3)
C12 C13 1.391(5)
C13 C14 1.347(4)
C14 N1 1.369(3)
C15 C16 1.360(3)
C16 C17 1.398(3)
C17 C18 1.365(3)
C18 C19 1.458(3)
C19 C24 1.391(3)
C19 C20 1.394(3)
C20 C21 1.371(3)
C21 C22 1.390(3)
C22 C23 1.381(3)
C22 N2 1.419(3)
C23 C24 1.376(3)
C25 C26 1.355(4)
C25 N2 1.372(3)
C26 C27 1.394(4)
C27 C28 1.351(4)
C28 N2 1.381(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661341
