#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/41/7054168.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_7054168
loop_
_publ_author_name
'Siddle, Jamie S.'
'Ward, Richard M.'
'Collings, Jonathan C.'
'Rutter, Simon R.'
'Porrés, Laurent'
'Applegarth, Lucas'
'Beeby, Andrew'
'Batsanov, Andrei S.'
'Thompson, Amber L.'
'Howard, Judith A. K.'
'Boucekkine, Abdou'
'Costuas, Karine'
'Halet, Jean-François'
'Marder, Todd B.'
_publ_section_title
;
 Synthesis, photophysics and molecular structures of luminescent
 2,5-bis(phenylethynyl)thiophenes (BPETs)
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              841
_journal_page_last               851
_journal_paper_doi               10.1039/b701172e
_journal_volume                  31
_journal_year                    2007
_chemical_formula_moiety         'C20 H12 S'
_chemical_formula_sum            'C20 H12 S'
_chemical_formula_weight         284.36
_chemical_name_systematic
;
2,5-bis(phenylethynyl)thiophene
;
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.87(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.752(1)
_cell_length_b                   5.7461(2)
_cell_length_c                   17.339(1)
_cell_measurement_reflns_used    2228
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.76
_cell_volume                     1469.60(14)
_computing_cell_refinement       'SAINT version 6.02A (Bruker, 2001)'
_computing_data_collection       'SMART-NT V5.049 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 6.02A (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL version 6.12 (Bruker, 2001)'
_computing_publication_material  'SHELXTL version 6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area detector'
_diffrn_measurement_method       ω-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  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0832
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9126
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (G.M.Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0497
_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)+(0.0557P)²+0.0887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                2098
_reflns_number_total             3365
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b701172e.txt
_cod_data_source_block           (1a)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7054168
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_symmetry_multiplicity
_atom_site_calc_flag
S1 S 0.17771(4) 0.10828(12) 0.92394(4) 0.02375(19) Uani 1 1 d
C2 C 0.08714(17) 0.1715(5) 0.86254(14) 0.0217(6) Uani 1 1 d
C3 C 0.01815(18) 0.0128(5) 0.87153(15) 0.0278(6) Uani 1 1 d
H3 H -0.0394(18) 0.020(5) 0.8419(15) 0.029(7) Uiso 1 1 d
C4 C 0.03784(18) -0.1601(5) 0.92702(15) 0.0260(6) Uani 1 1 d
H4 H -0.0028(19) -0.281(6) 0.9420(16) 0.040(8) Uiso 1 1 d
C5 C 0.12256(16) -0.1325(4) 0.96084(14) 0.0198(5) Uani 1 1 d
C6 C 0.09288(16) 0.3535(5) 0.80720(14) 0.0214(6) Uani 1 1 d
C7 C 0.09956(16) 0.4972(5) 0.75681(14) 0.0217(6) Uani 1 1 d
C8 C 0.16655(16) -0.2747(5) 1.01703(14) 0.0210(6) Uani 1 1 d
C9 C 0.20814(16) -0.3925(5) 1.06243(14) 0.0202(5) Uani 1 1 d
C11 C 0.10829(16) 0.6618(4) 0.69469(14) 0.0209(6) Uani 1 1 d
C12 C 0.16007(16) 0.8649(5) 0.70421(15) 0.0231(6) Uani 1 1 d
H12 H 0.1911(18) 0.906(5) 0.7512(15) 0.027(7) Uiso 1 1 d
C13 C 0.16802(18) 1.0231(5) 0.64401(15) 0.0238(6) Uani 1 1 d
H13 H 0.2004(19) 1.180(5) 0.6502(15) 0.034(8) Uiso 1 1 d
C14 C 0.12467(17) 0.9799(5) 0.57340(15) 0.0259(6) Uani 1 1 d
H14 H 0.1319(18) 1.097(5) 0.5319(16) 0.031(8) Uiso 1 1 d
C15 C 0.07443(17) 0.7778(5) 0.56310(15) 0.0257(6) Uani 1 1 d
H15 H 0.0426(17) 0.741(5) 0.5163(15) 0.024(7) Uiso 1 1 d
C16 C 0.06597(17) 0.6183(5) 0.62282(14) 0.0236(6) Uani 1 1 d
H16 H 0.0285(18) 0.480(5) 0.6189(14) 0.026(7) Uiso 1 1 d
C21 C 0.26149(16) -0.5409(4) 1.11266(13) 0.0187(5) Uani 1 1 d
C22 C 0.34980(17) -0.4768(5) 1.13566(14) 0.0204(5) Uani 1 1 d
H22 H 0.3743(18) -0.338(5) 1.1180(16) 0.033(8) Uiso 1 1 d
C23 C 0.40173(17) -0.6240(5) 1.18164(14) 0.0238(6) Uani 1 1 d
H23 H 0.4638(17) -0.586(5) 1.1970(13) 0.018(6) Uiso 1 1 d
C24 C 0.36626(18) -0.8353(5) 1.20675(15) 0.0251(6) Uani 1 1 d
H24 H 0.4003(19) -0.931(5) 1.2400(16) 0.034(8) Uiso 1 1 d
C25 C 0.27877(18) -0.9001(5) 1.18429(15) 0.0234(6) Uani 1 1 d
H25 H 0.2558(18) -1.047(5) 1.2032(15) 0.032(8) Uiso 1 1 d
C26 C 0.22689(17) -0.7556(5) 1.13754(14) 0.0210(6) Uani 1 1 d
H26 H 0.1640(18) -0.796(5) 1.1225(15) 0.029(7) Uiso 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'
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 91.84(12)
C3 C2 C6 127.9(2)
C3 C2 S1 110.8(2)
C6 C2 S1 121.0(2)
C2 C3 C4 113.5(2)
C2 C3 H3 122.9(17)
C4 C3 H3 123.6(17)
C5 C4 C3 112.6(2)
C5 C4 H4 122.3(18)
C3 C4 H4 125.0(18)
C4 C5 C8 128.7(2)
C4 C5 S1 111.2(2)
C8 C5 S1 120.02(18)
C7 C6 C2 175.7(3)
C6 C7 C11 177.9(3)
C9 C8 C5 176.4(3)
C8 C9 C21 176.1(3)
C12 C11 C16 119.0(2)
C12 C11 C7 120.8(2)
C16 C11 C7 120.1(2)
C13 C12 C11 120.5(2)
C13 C12 H12 115.6(17)
C11 C12 H12 123.9(17)
C12 C13 C14 120.0(3)
C12 C13 H13 122.8(16)
C14 C13 H13 117.0(16)
C15 C14 C13 119.9(3)
C15 C14 H14 122.5(16)
C13 C14 H14 117.6(17)
C14 C15 C16 120.7(3)
C14 C15 H15 123.4(17)
C16 C15 H15 115.9(17)
C15 C16 C11 119.9(3)
C15 C16 H16 123.1(15)
C11 C16 H16 116.8(15)
C26 C21 C22 118.8(2)
C26 C21 C9 120.4(2)
C22 C21 C9 120.7(2)
C23 C22 C21 120.3(2)
C23 C22 H22 120.0(17)
C21 C22 H22 119.6(17)
C22 C23 C24 120.3(2)
C22 C23 H23 121.8(16)
C24 C23 H23 117.8(16)
C25 C24 C23 119.7(3)
C25 C24 H24 120.0(18)
C23 C24 H24 120.2(18)
C26 C25 C24 120.3(3)
C26 C25 H25 121.9(17)
C24 C25 H25 117.7(17)
C25 C26 C21 120.4(2)
C25 C26 H26 121.5(17)
C21 C26 H26 118.0(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.732(3)
S1 C2 1.734(3)
C2 C3 1.377(4)
C2 C6 1.423(4)
C3 C4 1.410(4)
C3 H3 0.99(3)
C4 C5 1.382(4)
C4 H4 0.96(3)
C5 C8 1.421(3)
C6 C7 1.207(4)
C7 C11 1.441(4)
C8 C9 1.200(3)
C9 C21 1.444(3)
C11 C12 1.403(4)
C11 C16 1.408(3)
C12 C13 1.391(4)
C12 H12 0.96(3)
C13 C14 1.395(4)
C13 H13 1.03(3)
C14 C15 1.388(4)
C14 H14 0.99(3)
C15 C16 1.390(4)
C15 H15 0.95(3)
C16 H16 0.97(3)
C21 C26 1.406(4)
C21 C22 1.406(3)
C22 C23 1.386(4)
C22 H22 0.93(3)
C23 C24 1.394(4)
C23 H23 0.98(2)
C24 C25 1.393(4)
C24 H24 0.94(3)
C25 C26 1.383(4)
C25 H25 0.97(3)
C26 H26 0.99(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 14454664
