#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/25/1502574.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_1502574
loop_
_publ_author_name
'Guo, Xin'
'Wang, Suhao'
'Enkelmann, Volker'
'Baumgarten, Martin'
'Müllen, Klaus'
_publ_section_title
;
 Making benzotrithiophene a stronger electron donor.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6062
_journal_page_last               6065
_journal_paper_doi               10.1021/ol2025372
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C24 H30 S3'
_chemical_formula_sum            'C24 H30 S3'
_chemical_formula_weight         414.70
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-02-17
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 117.120(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2751(4)
_cell_length_b                   11.0342(6)
_cell_length_c                   14.3941(9)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    120
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2159.4(2)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12447
_diffrn_reflns_theta_full        29.539
_diffrn_reflns_theta_max         29.539
_diffrn_reflns_theta_min         2.997
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0233
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0771
_refine_ls_shift/su_max          0.008910
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;

 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 

 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 

 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 

 Method = Robust Weighting (Prince, 1982) 

 W = [weight] * [1-(deltaF/6*sigmaF)²]² 

 Ai are: 

 2.77 0.781 1.97 

;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0887
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0859
_reflns_limit_h_max              18
_reflns_limit_h_min              -21
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2225
_reflns_number_total             3012
_reflns_threshold_expression     I>3.0σ(I)
_cod_data_source_file            ol2025372_si_002.cif
_cod_data_source_block           guo4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               1502574
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.0000 0.04299(8) 0.2500 0.0250 1.0000 Uani S T
S2 S 0.12790(5) 0.61250(6) 0.31012(6) 0.0259 1.0000 Uani . .
C1 C 0.2313(2) 0.5222(3) 0.3614(2) 0.0277 1.0000 Uani . .
C2 C 0.2095(2) 0.4014(2) 0.3528(2) 0.0248 1.0000 Uani . .
C3 C 0.1069(2) 0.3800(2) 0.3044(2) 0.0187 1.0000 Uani . .
C4 C 0.05224(18) 0.4877(2) 0.2752(2) 0.0232 1.0000 Uani . .
C5 C 0.05349(18) 0.2641(2) 0.2767(2) 0.0229 1.0000 Uani . .
C6 C 0.09249(19) 0.1475(2) 0.2966(2) 0.0235 1.0000 Uani . .
C7 C 0.1991(2) 0.1105(2) 0.3513(2) 0.0246 1.0000 Uani . .
C8 C 0.2185(2) -0.0251(3) 0.3615(2) 0.0265 1.0000 Uani . .
C9 C 0.32958(19) -0.0486(2) 0.4167(2) 0.0245 1.0000 Uani . .
C10 C 0.3567(2) -0.1827(2) 0.4311(2) 0.0245 1.0000 Uani . .
C11 C 0.4684(2) -0.2016(2) 0.4895(2) 0.0284 1.0000 Uani . .
C12 C 0.4973(2) -0.3352(3) 0.5080(3) 0.0380 1.0000 Uani . .
H11 H 0.2967 0.5525 0.3928 0.0360 1.0000 Uiso R .
H21 H 0.2571 0.3384 0.3767 0.0347 1.0000 Uiso R .
H71 H 0.2280 0.1441 0.4196 0.0339 1.0000 Uiso R .
H72 H 0.2303 0.1433 0.3130 0.0339 1.0000 Uiso R .
H81 H 0.1898 -0.0597 0.4016 0.0356 1.0000 Uiso R .
H82 H 0.1901 -0.0609 0.2940 0.0356 1.0000 Uiso R .
H91 H 0.3570 -0.0112 0.4834 0.0334 1.0000 Uiso R .
H92 H 0.3572 -0.0134 0.3757 0.0334 1.0000 Uiso R .
H101 H 0.3275 -0.2192 0.4699 0.0327 1.0000 Uiso R .
H102 H 0.3321 -0.2202 0.3645 0.0327 1.0000 Uiso R .
H111 H 0.4932 -0.1614 0.5550 0.0400 1.0000 Uiso R .
H112 H 0.4972 -0.1676 0.4493 0.0400 1.0000 Uiso R .
H121 H 0.5668 -0.3434 0.5442 0.0476 1.0000 Uiso R .
H122 H 0.4689 -0.3698 0.5484 0.0476 1.0000 Uiso R .
H123 H 0.4730 -0.3759 0.4428 0.0476 1.0000 Uiso R .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 5_555 S1 C6 . 94.97(18) yes
C1 . S2 C4 . 91.42(13) yes
S2 . C1 C2 . 112.8(2) yes
S2 . C1 H11 . 124.0 no
C2 . C1 H11 . 123.2 no
C1 . C2 C3 . 112.2(2) yes
C1 . C2 H21 . 124.5 no
C3 . C2 H21 . 123.3 no
C2 . C3 C4 . 112.4(2) yes
C2 . C3 C5 . 129.2(2) yes
C4 . C3 C5 . 118.3(2) yes
C4 5_555 C4 C3 . 122.01(15) yes
C4 5_555 C4 S2 . 126.76(9) yes
C3 . C4 S2 . 111.22(19) yes
C3 . C5 C5 5_555 119.63(14) yes
C3 . C5 C6 . 128.0(2) yes
C5 5_555 C5 C6 . 112.40(15) yes
C5 . C6 S1 . 110.12(19) yes
C5 . C6 C7 . 128.1(2) yes
S1 . C6 C7 . 121.77(19) yes
C6 . C7 C8 . 115.7(2) yes
C6 . C7 H71 . 108.5 no
C8 . C7 H71 . 107.8 no
C6 . C7 H72 . 107.6 no
C8 . C7 H72 . 107.7 no
H71 . C7 H72 . 109.5 no
C7 . C8 C9 . 109.7(2) yes
C7 . C8 H81 . 109.3 no
C9 . C8 H81 . 109.0 no
C7 . C8 H82 . 109.4 no
C9 . C8 H82 . 110.0 no
H81 . C8 H82 . 109.5 no
C8 . C9 C10 . 113.8(2) yes
C8 . C9 H91 . 109.0 no
C10 . C9 H91 . 108.5 no
C8 . C9 H92 . 108.0 no
C10 . C9 H92 . 108.1 no
H91 . C9 H92 . 109.5 no
C9 . C10 C11 . 111.8(2) yes
C9 . C10 H101 . 108.7 no
C11 . C10 H101 . 108.9 no
C9 . C10 H102 . 109.1 no
C11 . C10 H102 . 108.9 no
H101 . C10 H102 . 109.5 no
C10 . C11 C12 . 112.8(2) yes
C10 . C11 H111 . 108.7 no
C12 . C11 H111 . 109.0 no
C10 . C11 H112 . 108.7 no
C12 . C11 H112 . 108.1 no
H111 . C11 H112 . 109.5 no
C11 . C12 H121 . 110.5 no
C11 . C12 H122 . 108.5 no
H121 . C12 H122 . 109.5 no
C11 . C12 H123 . 109.4 no
H121 . C12 H123 . 109.5 no
H122 . C12 H123 . 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C6 5_555 1.706(3) yes
S1 C6 . 1.706(3) yes
S2 C1 . 1.723(3) yes
S2 C4 . 1.719(3) yes
C1 C2 . 1.366(4) yes
C1 H11 . 0.950 no
C2 C3 . 1.414(4) yes
C2 H21 . 0.950 no
C3 C4 . 1.403(3) yes
C3 C5 . 1.470(3) yes
C4 C4 5_555 1.420(5) yes
C5 C5 5_555 1.455(5) yes
C5 C6 . 1.392(4) yes
C6 C7 . 1.506(4) yes
C7 C8 . 1.520(4) yes
C7 H71 . 0.950 no
C7 H72 . 0.950 no
C8 C9 . 1.532(4) yes
C8 H81 . 0.950 no
C8 H82 . 0.950 no
C9 C10 . 1.525(4) yes
C9 H91 . 0.950 no
C9 H92 . 0.950 no
C10 C11 . 1.534(4) yes
C10 H101 . 0.950 no
C10 H102 . 0.950 no
C11 C12 . 1.527(4) yes
C11 H111 . 0.950 no
C11 H112 . 0.950 no
C12 H121 . 0.950 no
C12 H122 . 0.950 no
C12 H123 . 0.950 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101539488
