#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025242.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_4025242
loop_
_publ_author_name
'Shoji Shinamura'
'Eigo Miyazaki'
'Kazuo Takimiya'
_publ_section_title
;
 Synthesis, Properties, Crystal Structures, and Semiconductor
 Characteristics of Naphtho[1,2-b:5,6-b']dithiophene and -diselenophene
 Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1228
_journal_page_last               1234
_journal_paper_doi               10.1021/jo902545a
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C30 H40 S2'
_chemical_formula_sum            'C30 H40 S2'
_chemical_formula_weight         464.74
_chemical_name_common            C8-NDT
_chemical_name_systematic
; 
 C8-NDT 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.24(2)
_cell_angle_beta                 98.78(2)
_cell_angle_gamma                93.683(19)
_cell_formula_units_Z            1
_cell_length_a                   5.369(9)
_cell_length_b                   11.119(19)
_cell_length_c                   12.03(2)
_cell_measurement_reflns_used    1774
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     665.0(19)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 14.71
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1053
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2843
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_diffrn_standards_number         5072
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.730
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.730
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0518
_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)+(0.0623P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                1449
_reflns_number_total             2843
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902545a_si_001_3.cif
_cod_data_source_block           C8-NDT
_cod_original_cell_volume        665(2)
_cod_database_code               4025242
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.30205(11) 0.78796(6) 1.01441(6) 0.0578(2) Uani 1 1 d . . .
C1 C 0.0878(4) 0.5379(2) 0.98239(19) 0.0445(5) Uani 1 1 d . . .
C2 C 0.1070(4) 0.6733(2) 1.0398(2) 0.0461(5) Uani 1 1 d . . .
C3 C -0.0363(4) 0.7316(2) 1.1258(2) 0.0486(6) Uani 1 1 d . . .
C4 C -0.2099(4) 0.6514(2) 1.1579(2) 0.0554(6) Uani 1 1 d . . .
C5 C -0.2336(4) 0.5212(2) 1.1047(2) 0.0529(6) Uani 1 1 d . . .
C6 C 0.0159(4) 0.8691(2) 1.1683(2) 0.0538(6) Uani 1 1 d . . .
C7 C 0.1910(4) 0.9134(2) 1.1167(2) 0.0513(6) Uani 1 1 d . . .
C8 C 0.2955(5) 1.0490(2) 1.1346(2) 0.0591(6) Uani 1 1 d . . .
C9 C 0.1918(4) 1.1534(2) 1.2258(2) 0.0590(6) Uani 1 1 d . . .
C10 C 0.3054(4) 1.2872(2) 1.2374(2) 0.0580(6) Uani 1 1 d . . .
C11 C 0.2035(5) 1.3956(2) 1.3254(2) 0.0618(7) Uani 1 1 d . . .
C12 C 0.3234(4) 1.5289(2) 1.3391(2) 0.0581(6) Uani 1 1 d . . .
C13 C 0.2249(5) 1.6376(2) 1.4281(2) 0.0625(7) Uani 1 1 d . . .
C14 C 0.3459(5) 1.7707(2) 1.4427(2) 0.0700(8) Uani 1 1 d . . .
C15 C 0.2374(6) 1.8782(3) 1.5303(3) 0.1036(11) Uani 1 1 d . . .
H1 H -0.3100 0.6894 1.2173 0.068 Uiso 1 1 d . . .
H2 H -0.3458 0.4676 1.1296 0.064 Uiso 1 1 d . . .
H3 H -0.0665 0.9238 1.2295 0.064 Uiso 1 1 d . . .
H4 H 0.4756 1.0597 1.1588 0.074 Uiso 1 1 d . . .
H5 H 0.2579 1.0631 1.0594 0.074 Uiso 1 1 d . . .
H6 H 0.0116 1.1447 1.2023 0.072 Uiso 1 1 d . . .
H7 H 0.2304 1.1420 1.3015 0.072 Uiso 1 1 d . . .
H8 H 0.4850 1.2957 1.2619 0.073 Uiso 1 1 d . . .
H9 H 0.2704 1.2968 1.1602 0.073 Uiso 1 1 d . . .
H10 H 0.0244 1.3885 1.2990 0.076 Uiso 1 1 d . . .
H11 H 0.2343 1.3846 1.4014 0.076 Uiso 1 1 d . . .
H12 H 0.5027 1.5358 1.3637 0.072 Uiso 1 1 d . . .
H13 H 0.2912 1.5403 1.2623 0.072 Uiso 1 1 d . . .
H14 H 0.0446 1.6326 1.4022 0.079 Uiso 1 1 d . . .
H15 H 0.2537 1.6267 1.5039 0.079 Uiso 1 1 d . . .
H16 H 0.5237 1.7769 1.4692 0.085 Uiso 1 1 d . . .
H17 H 0.3171 1.7818 1.3660 0.085 Uiso 1 1 d . . .
H18 H 0.2687 1.8691 1.6077 0.125 Uiso 1 1 d . . .
H19 H 0.3190 1.9593 1.5368 0.125 Uiso 1 1 d . . .
H20 H 0.0609 1.8733 1.5047 0.125 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C7 92.50(16) . . yes
C5 C1 C1 120.6(3) 2_567 2_567 yes
C5 C1 C2 123.11(19) 2_567 . yes
C1 C1 C2 116.3(3) 2_567 . yes
C3 C2 C1 123.1(2) . . yes
C3 C2 S1 110.53(19) . . yes
C1 C2 S1 126.33(19) . . yes
C2 C3 C4 118.4(2) . . yes
C2 C3 C6 112.1(2) . . yes
C4 C3 C6 129.5(2) . . yes
C5 C4 C3 120.1(2) . . yes
C4 C5 C1 121.5(2) . 2_567 yes
C7 C6 C3 113.7(2) . . yes
C6 C7 C8 130.4(2) . . yes
C6 C7 S1 111.2(2) . . yes
C8 C7 S1 118.37(19) . . yes
C7 C8 C9 115.5(2) . . yes
C8 C9 C10 112.0(2) . . yes
C11 C10 C9 114.3(2) . . yes
C10 C11 C12 114.0(2) . . yes
C13 C12 C11 114.2(2) . . yes
C12 C13 C14 114.4(2) . . yes
C13 C14 C15 113.1(3) . . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.732(3) . yes
S1 C7 1.736(3) . yes
C1 C5 1.416(3) 2_567 yes
C1 C1 1.426(4) 2_567 yes
C1 C2 1.424(4) . yes
C2 C3 1.395(3) . yes
C3 C4 1.429(3) . yes
C3 C6 1.437(4) . yes
C4 C5 1.365(4) . yes
C5 C1 1.416(3) 2_567 yes
C6 C7 1.354(3) . yes
C7 C8 1.509(4) . yes
C8 C9 1.514(4) . yes
C9 C10 1.525(4) . yes
C10 C11 1.515(4) . yes
C11 C12 1.523(4) . yes
C12 C13 1.514(4) . yes
C13 C14 1.521(4) . yes
C14 C15 1.525(4) . yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 -179.9(2) 2_567 . . . yes
C1 C1 C2 C3 -0.2(4) 2_567 . . . yes
C5 C1 C2 S1 0.7(3) 2_567 . . . yes
C1 C1 C2 S1 -179.66(19) 2_567 . . . yes
C7 S1 C2 C3 -0.63(18) . . . . yes
C7 S1 C2 C1 178.8(2) . . . . yes
C1 C2 C3 C4 0.2(3) . . . . yes
S1 C2 C3 C4 179.67(17) . . . . yes
C1 C2 C3 C6 -179.1(2) . . . . yes
S1 C2 C3 C6 0.4(3) . . . . yes
C2 C3 C4 C5 -0.2(3) . . . . yes
C6 C3 C4 C5 178.9(2) . . . . yes
C3 C4 C5 C1 0.4(4) . . . 2_567 yes
C2 C3 C6 C7 0.1(3) . . . . yes
C4 C3 C6 C7 -179.0(2) . . . . yes
C3 C6 C7 C8 179.2(2) . . . . yes
C3 C6 C7 S1 -0.6(3) . . . . yes
C2 S1 C7 C6 0.69(19) . . . . yes
C2 S1 C7 C8 -179.07(18) . . . . yes
C6 C7 C8 C9 0.8(4) . . . . yes
S1 C7 C8 C9 -179.50(17) . . . . yes
C7 C8 C9 C10 -179.46(19) . . . . yes
C8 C9 C10 C11 178.6(2) . . . . yes
C9 C10 C11 C12 178.36(19) . . . . yes
C10 C11 C12 C13 -179.2(2) . . . . yes
C11 C12 C13 C14 179.5(2) . . . . yes
C12 C13 C14 C15 178.4(2) . . . . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 45112763
