#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/55/2215572.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2215572
loop_
_publ_author_name
'Lei Liu'
'Wei Xu'
'Xun-Wen Xiao'
'Dao-Ben Zhu'
_publ_section_title
3,3',4,4'-Tetrabutyl-5,5'-(biphenyl-4,4'-diyldiethynyl)bis(thiophene-2-carbonitrile)
_journal_coeditor_code           KP2126
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3961
_journal_page_last               o3961
_journal_paper_doi               10.1107/S1600536807041578
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C42 H44 N2 S2'
_chemical_formula_moiety         'C42 H44 N2 S2'
_chemical_formula_sum            'C42 H44 N2 S2'
_chemical_formula_weight         640.91
_chemical_name_systematic
;
3,3',4,4'-Tetrabutyl-5,5'-(biphenyl-4,4'-diyldiethynyl)bis(thiophene-2-\
carbonitrile)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.37(3)
_cell_angle_beta                 100.53(3)
_cell_angle_gamma                112.32(3)
_cell_formula_units_Z            1
_cell_length_a                   8.1428(16)
_cell_length_b                   9.1856(18)
_cell_length_c                   13.606(3)
_cell_measurement_temperature    293(2)
_cell_volume                     922.4(4)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 2001)'
_computing_data_reduction        RAPID-AUTO
_computing_molecular_graphics
;
SHELXTL (Siemens, 1994 or Bruker, 1998) or XP (Bruker,
1998)?
;
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.76
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       Oscillation
_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  0.029
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5834
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.8791
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             342
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.387
_exptl_crystal_size_min          0.281
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0711
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1503P)²+0.3412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2178
_refine_ls_wR_factor_ref         0.2354
_reflns_number_gt                3287
_reflns_number_total             4080
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2126.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        922.3(3)
_cod_database_code               2215572
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.28848(9) 0.32421(9) 0.44787(5) 0.0608(3) Uani d . 1
C C1 0.1734(4) 0.2078(4) 0.8390(2) 0.0766(9) Uani d . 1
H H1A 0.2773 0.2920 0.8308 0.092 Uiso calc R 1
N N1 0.4301(5) 0.4639(4) 0.2102(3) 0.1016(11) Uani d . 1
C C2 0.1583(4) 0.1546(4) 0.9336(2) 0.0752(9) Uani d . 1
H H2A 0.2524 0.2049 0.9878 0.090 Uiso calc R 1
C C3 0.0075(3) 0.0290(3) 0.94934(16) 0.0469(5) Uani d . 1
C C4 -0.1306(4) -0.0409(3) 0.86606(19) 0.0639(7) Uani d . 1
H H4A -0.2353 -0.1245 0.8740 0.077 Uiso calc R 1
C C5 -0.1156(4) 0.0112(3) 0.77223(19) 0.0662(7) Uani d . 1
H H5A -0.2095 -0.0393 0.7179 0.079 Uiso calc R 1
C C6 0.0349(4) 0.1361(3) 0.75692(17) 0.0533(6) Uani d . 1
C C7 0.0492(4) 0.1910(3) 0.65898(19) 0.0574(6) Uani d . 1
C C8 0.0589(4) 0.2360(3) 0.57725(18) 0.0556(6) Uani d . 1
C C9 0.0843(3) 0.2910(3) 0.48107(17) 0.0506(5) Uani d . 1
C C10 -0.0335(3) 0.3280(3) 0.40904(17) 0.0492(5) Uani d . 1
C C11 0.0437(4) 0.3854(3) 0.32413(18) 0.0534(6) Uani d . 1
C C12 0.2171(4) 0.3890(3) 0.3356(2) 0.0589(6) Uani d . 1
C C13 0.3348(5) 0.4322(4) 0.2656(2) 0.0717(8) Uani d . 1
C C14 -0.2209(4) 0.3068(3) 0.4213(2) 0.0589(6) Uani d . 1
H H14A -0.2454 0.3970 0.3970 0.071 Uiso calc R 1
H H14B -0.2242 0.3058 0.4922 0.071 Uiso calc R 1
C C15 -0.0488(5) 0.4360(4) 0.2334(2) 0.0686(8) Uani d . 1
H H15A 0.0366 0.5335 0.2151 0.082 Uiso calc R 1
H H15B -0.1478 0.4583 0.2507 0.082 Uiso calc R 1
C C16 -0.3690(4) 0.1584(4) 0.3671(3) 0.0848(10) Uani d . 1
H H16A -0.4820 0.1504 0.3849 0.102 Uiso calc R 1
H H16B -0.3809 0.1699 0.2957 0.102 Uiso calc R 1
C C17 -0.1229(5) 0.3166(5) 0.1432(2) 0.0803(9) Uani d . 1
H H17A -0.1959 0.2149 0.1632 0.096 Uiso calc R 1
H H17B -0.0227 0.3054 0.1193 0.096 Uiso calc R 1
C C18 -0.3470(6) 0.0111(5) 0.3857(4) 0.1018(13) Uani d . 1
H H18A -0.3299 0.0015 0.4574 0.122 Uiso calc R 1
H H18B -0.2369 0.0170 0.3650 0.122 Uiso calc R 1
C C19 -0.2385(7) 0.3634(6) 0.0574(3) 0.1009(13) Uani d . 1
H H19A -0.3402 0.3718 0.0810 0.121 Uiso calc R 1
H H19B -0.1663 0.4668 0.0392 0.121 Uiso calc R 1
C C20 -0.5024(6) -0.1393(4) 0.3335(4) 0.0994(12) Uani d . 1
H H20A -0.4765 -0.2298 0.3532 0.149 Uiso calc R 1
H H20B -0.5152 -0.1357 0.2621 0.149 Uiso calc R 1
H H20C -0.6130 -0.1468 0.3526 0.149 Uiso calc R 1
C C21 -0.3088(8) 0.2507(7) -0.0336(3) 0.1312(19) Uani d . 1
H H21A -0.3806 0.2867 -0.0838 0.197 Uiso calc R 1
H H21B -0.3823 0.1483 -0.0167 0.197 Uiso calc R 1
H H21C -0.2091 0.2443 -0.0590 0.197 Uiso calc R 1
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_site_symmetry_3
_geom_angle
C9 S1 C12 . 90.36(13)
C6 C1 C2 . 120.4(3)
C6 C1 H1A . 119.8
C2 C1 H1A . 119.8
C3 C2 C1 . 121.9(3)
C3 C2 H2A . 119.1
C1 C2 H2A . 119.1
C2 C3 C4 . 116.9(2)
C2 C3 C3 2_557 121.7(3)
C4 C3 C3 2_557 121.4(3)
C5 C4 C3 . 121.4(3)
C5 C4 H4A . 119.3
C3 C4 H4A . 119.3
C6 C5 C4 . 121.5(3)
C6 C5 H5A . 119.2
C4 C5 H5A . 119.2
C5 C6 C1 . 117.9(2)
C5 C6 C7 . 121.3(2)
C1 C6 C7 . 120.8(3)
C8 C7 C6 . 179.2(3)
C7 C8 C9 . 175.7(3)
C10 C9 C8 . 128.5(2)
C10 C9 S1 . 113.10(18)
C8 C9 S1 . 118.34(19)
C9 C10 C11 . 112.0(2)
C9 C10 C14 . 122.5(2)
C11 C10 C14 . 125.5(2)
C12 C11 C10 . 111.3(2)
C12 C11 C15 . 123.5(2)
C10 C11 C15 . 125.2(3)
C11 C12 C13 . 128.0(3)
C11 C12 S1 . 113.28(19)
C13 C12 S1 . 118.7(2)
N1 C13 C12 . 178.3(4)
C10 C14 C16 . 114.4(2)
C10 C14 H14A . 108.7
C16 C14 H14A . 108.7
C10 C14 H14B . 108.7
C16 C14 H14B . 108.7
H14A C14 H14B . 107.6
C11 C15 C17 . 114.6(2)
C11 C15 H15A . 108.6
C17 C15 H15A . 108.6
C11 C15 H15B . 108.6
C17 C15 H15B . 108.6
H15A C15 H15B . 107.6
C18 C16 C14 . 117.0(3)
C18 C16 H16A . 108.0
C14 C16 H16A . 108.0
C18 C16 H16B . 108.0
C14 C16 H16B . 108.0
H16A C16 H16B . 107.3
C15 C17 C19 . 112.6(3)
C15 C17 H17A . 109.1
C19 C17 H17A . 109.1
C15 C17 H17B . 109.1
C19 C17 H17B . 109.1
H17A C17 H17B . 107.8
C16 C18 C20 . 116.4(4)
C16 C18 H18A . 108.2
C20 C18 H18A . 108.2
C16 C18 H18B . 108.2
C20 C18 H18B . 108.2
H18A C18 H18B . 107.4
C21 C19 C17 . 114.0(4)
C21 C19 H19A . 108.8
C17 C19 H19A . 108.8
C21 C19 H19B . 108.8
C17 C19 H19B . 108.8
H19A C19 H19B . 107.7
C18 C20 H20A . 109.5
C18 C20 H20B . 109.5
H20A C20 H20B . 109.5
C18 C20 H20C . 109.5
H20A C20 H20C . 109.5
H20B C20 H20C . 109.5
C19 C21 H21A . 109.5
C19 C21 H21B . 109.5
H21A C21 H21B . 109.5
C19 C21 H21C . 109.5
H21A C21 H21C . 109.5
H21B C21 H21C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C9 . 1.718(3)
S1 C12 . 1.725(3)
C1 C6 . 1.386(4)
C1 C2 . 1.389(4)
C1 H1A . 0.9300
N1 C13 . 1.140(4)
C2 C3 . 1.381(4)
C2 H2A . 0.9300
C3 C4 . 1.392(4)
C3 C3 2_557 1.490(4)
C4 C5 . 1.376(4)
C4 H4A . 0.9300
C5 C6 . 1.375(4)
C5 H5A . 0.9300
C6 C7 . 1.437(3)
C7 C8 . 1.195(4)
C8 C9 . 1.428(3)
C9 C10 . 1.380(4)
C10 C11 . 1.425(3)
C10 C14 . 1.504(4)
C11 C12 . 1.380(4)
C11 C15 . 1.497(4)
C12 C13 . 1.425(4)
C14 C16 . 1.506(4)
C14 H14A . 0.9700
C14 H14B . 0.9700
C15 C17 . 1.511(4)
C15 H15A . 0.9700
C15 H15B . 0.9700
C16 C18 . 1.448(5)
C16 H16A . 0.9700
C16 H16B . 0.9700
C17 C19 . 1.531(5)
C17 H17A . 0.9700
C17 H17B . 0.9700
C18 C20 . 1.532(6)
C18 H18A . 0.9700
C18 H18B . 0.9700
C19 C21 . 1.484(6)
C19 H19A . 0.9700
C19 H19B . 0.9700
C20 H20A . 0.9600
C20 H20B . 0.9600
C20 H20C . 0.9600
C21 H21A . 0.9600
C21 H21B . 0.9600
C21 H21C . 0.9600
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
C12 C11 C10 C9 0.1(3)
C12 S1 C9 C10 0.0(3)
C10 C11 C12 S1 -0.10(10)
C11 C12 S1 C9 0.0(5)
C11 C10 C9 S1 -0.1(3)
C11 C10 C9 C8 177.5(5)
C12 S1 C9 C8 -177.8(8)
C7 C6 C5 C4 -179.40(10)
C7 C6 C1 C2 179.6(8)
C6 C5 C4 C3 -1.1(5)
C6 C1 C2 C3 0.5(7)
C4 C5 C6 C1 0.7(2)
C1 C2 C3 C4 -0.9(5)
C5 C4 C3 C2 1.1(6)
C5 C6 C1 C2 -0.4(5)
C12 C11 C15 C17 77.9(4)
C11 C15 C17 C19 172.0(7)
C15 C17 C19 C21 178.2(5)
C10 C11 C15 C17 -102.1(3)
C11 C10 C14 C16 79.8(7)
C9 C10 C14 C16 -99.4(5)
C10 C14 C16 C18 52.3(7)
C14 C16 C18 C20 177.5(2)
C4 C3 C3 C4 90.00(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102277279
