#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/41/7054169.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_7054169
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         'C22 H16 S'
_chemical_formula_sum            'C22 H16 S'
_chemical_formula_weight         312.41
_chemical_melting_point          441.3(2)
_chemical_name_systematic
;
2,5-bis(p-methylphenylethynyl)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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.217(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0717(15)
_cell_length_b                   5.0902(5)
_cell_length_c                   21.2336(19)
_cell_measurement_reflns_used    5758
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.00
_cell_measurement_theta_min      2.74
_cell_volume                     1608.1(3)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17948
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0464
_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)+(0.0449P)²+0.7678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                3243
_reflns_number_total             4255
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b701172e.txt
_cod_data_source_block           (1b)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7054169
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 0.45063(3) 0.91711(8) 0.23334(2) 0.02171(11) Uani 1 1 d
C2 C 0.52393(10) 1.0970(3) 0.20831(8) 0.0207(3) Uani 1 1 d
C3 C 0.51632(12) 1.0262(4) 0.14365(9) 0.0262(4) Uani 1 1 d
H3 H 0.5533(13) 1.106(4) 0.1225(10) 0.029(5) Uiso 1 1 d
C4 C 0.45182(12) 0.8292(4) 0.11490(9) 0.0259(4) Uani 1 1 d
H4 H 0.4373(14) 0.759(4) 0.0700(11) 0.038(6) Uiso 1 1 d
C5 C 0.40971(11) 0.7482(3) 0.15721(8) 0.0203(3) Uani 1 1 d
C6 C 0.58067(11) 1.2895(3) 0.25284(8) 0.0214(3) Uani 1 1 d
C7 C 0.62661(11) 1.4485(3) 0.29063(8) 0.0211(3) Uani 1 1 d
C8 C 0.34203(11) 0.5550(3) 0.14575(8) 0.0220(3) Uani 1 1 d
C9 C 0.28599(11) 0.3939(3) 0.13813(8) 0.0207(3) Uani 1 1 d
C10 C 0.85960(13) 2.2149(4) 0.47319(10) 0.0284(4) Uani 1 1 d
H101 H 0.8554(15) 2.210(5) 0.5175(12) 0.048(6) Uiso 1 1 d
H102 H 0.9239(16) 2.180(4) 0.4794(11) 0.045(6) Uiso 1 1 d
H103 H 0.8471(16) 2.387(5) 0.4544(12) 0.051(7) Uiso 1 1 d
C11 C 0.68423(11) 1.6423(3) 0.33608(8) 0.0199(3) Uani 1 1 d
C12 C 0.67575(12) 1.7019(4) 0.39762(9) 0.0248(4) Uani 1 1 d
H12 H 0.6306(13) 1.613(4) 0.4087(10) 0.032(5) Uiso 1 1 d
C13 C 0.73271(12) 1.8849(3) 0.44190(9) 0.0253(4) Uani 1 1 d
H13 H 0.7274(13) 1.920(4) 0.4855(10) 0.033(5) Uiso 1 1 d
C14 C 0.79826(11) 2.0148(3) 0.42577(8) 0.0214(3) Uani 1 1 d
C15 C 0.80553(11) 1.9565(3) 0.36386(8) 0.0231(4) Uani 1 1 d
H15 H 0.8497(14) 2.043(4) 0.3512(10) 0.035(6) Uiso 1 1 d
C16 C 0.74986(12) 1.7731(3) 0.31965(8) 0.0222(3) Uani 1 1 d
H16 H 0.7565(13) 1.737(4) 0.2770(10) 0.031(5) Uiso 1 1 d
C20 C 0.00475(12) -0.3718(4) 0.09202(9) 0.0250(4) Uani 1 1 d
H201 H -0.0364(13) -0.363(4) 0.0457(11) 0.034(5) Uiso 1 1 d
H202 H -0.0297(14) -0.337(4) 0.1196(10) 0.035(5) Uiso 1 1 d
H203 H 0.0297(13) -0.551(4) 0.1035(10) 0.031(5) Uiso 1 1 d
C21 C 0.21708(11) 0.1981(3) 0.12767(8) 0.0199(3) Uani 1 1 d
C22 C 0.18748(12) 0.1286(3) 0.17949(8) 0.0234(4) Uani 1 1 d
H22 H 0.2144(13) 0.210(4) 0.2235(10) 0.032(5) Uiso 1 1 d
C23 C 0.11938(12) -0.0537(3) 0.16767(8) 0.0236(4) Uani 1 1 d
H23 H 0.0988(13) -0.090(4) 0.2048(10) 0.031(5) Uiso 1 1 d
C24 C 0.07843(11) -0.1739(3) 0.10446(8) 0.0205(3) Uani 1 1 d
C25 C 0.10907(12) -0.1061(4) 0.05326(8) 0.0250(4) Uani 1 1 d
H25 H 0.0837(13) -0.186(4) 0.0094(10) 0.031(5) Uiso 1 1 d
C26 C 0.17698(11) 0.0751(3) 0.06426(8) 0.0239(3) Uani 1 1 d
H26 H 0.1984(12) 0.117(4) 0.0274(10) 0.026(5) 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 92.21(8)
C3 C2 C6 129.29(15)
C3 C2 S1 110.72(12)
C6 C2 S1 119.99(12)
C2 C3 C4 113.09(15)
C2 C3 H3 121.2(12)
C4 C3 H3 125.7(12)
C5 C4 C3 113.21(15)
C5 C4 H4 122.8(13)
C3 C4 H4 124.0(12)
C4 C5 C8 129.09(15)
C4 C5 S1 110.77(12)
C8 C5 S1 120.14(12)
C7 C6 C2 178.53(17)
C6 C7 C11 178.69(17)
C9 C8 C5 178.10(17)
C8 C9 C21 179.07(17)
C14 C10 H101 111.4(14)
C14 C10 H102 110.4(13)
H101 C10 H102 108.4(18)
C14 C10 H103 111.1(14)
H101 C10 H103 110(2)
H102 C10 H103 105.0(19)
C12 C11 C16 118.63(15)
C12 C11 C7 120.57(15)
C16 C11 C7 120.80(14)
C13 C12 C11 120.33(16)
C13 C12 H12 121.2(12)
C11 C12 H12 118.5(12)
C14 C13 C12 121.14(16)
C14 C13 H13 119.4(12)
C12 C13 H13 119.5(12)
C13 C14 C15 118.16(15)
C13 C14 C10 121.41(15)
C15 C14 C10 120.43(16)
C16 C15 C14 121.27(16)
C16 C15 H15 118.6(12)
C14 C15 H15 120.2(12)
C15 C16 C11 120.46(15)
C15 C16 H16 119.4(12)
C11 C16 H16 120.2(12)
C24 C20 H201 110.0(12)
C24 C20 H202 111.6(12)
H201 C20 H202 106.5(17)
C24 C20 H203 110.9(11)
H201 C20 H203 110.8(17)
H202 C20 H203 106.9(17)
C22 C21 C26 118.24(15)
C22 C21 C9 121.50(15)
C26 C21 C9 120.25(14)
C23 C22 C21 120.51(15)
C23 C22 H22 120.0(12)
C21 C22 H22 119.5(12)
C22 C23 C24 121.49(15)
C22 C23 H23 117.6(11)
C24 C23 H23 120.8(11)
C23 C24 C25 117.69(15)
C23 C24 C20 121.23(15)
C25 C24 C20 121.08(15)
C26 C25 C24 121.51(16)
C26 C25 H25 117.9(12)
C24 C25 H25 120.5(12)
C25 C26 C21 120.55(15)
C25 C26 H26 119.9(11)
C21 C26 H26 119.5(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.7266(16)
S1 C2 1.7268(17)
C2 C3 1.379(2)
C2 C6 1.426(2)
C3 C4 1.405(2)
C3 H3 0.959(19)
C4 C5 1.377(2)
C4 H4 0.96(2)
C5 C8 1.418(2)
C6 C7 1.182(2)
C7 C11 1.444(2)
C8 C9 1.183(2)
C9 C21 1.443(2)
C10 C14 1.507(2)
C10 H101 0.97(2)
C10 H102 1.01(2)
C10 H103 0.95(2)
C11 C12 1.398(2)
C11 C16 1.398(2)
C12 C13 1.392(2)
C12 H12 0.96(2)
C13 C14 1.392(2)
C13 H13 0.98(2)
C14 C15 1.395(2)
C15 C16 1.385(2)
C15 H15 0.96(2)
C16 H16 0.968(19)
C20 C24 1.500(2)
C20 H201 0.96(2)
C20 H202 0.96(2)
C20 H203 0.99(2)
C21 C22 1.399(2)
C21 C26 1.401(2)
C22 C23 1.384(2)
C22 H22 0.96(2)
C23 C24 1.393(2)
C23 H23 0.98(2)
C24 C25 1.396(2)
C25 C26 1.380(2)
C25 H25 0.95(2)
C26 H26 0.989(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 628545
