#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:30:04 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301811 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/31/4003188.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_4003188
loop_
_publ_author_name
'Nakano, Masahiro'
'Osaka, Itaru'
'Hashizume, Daisuke'
'Takimiya, Kazuo'
_publ_section_title
;
 α-Modified Naphthodithiophene Diimides---Molecular Design Strategy for
 Air-Stable n-Channel Organic Semiconductors
;
_journal_issue                   18
_journal_name_full               'Chemistry of Materials'
_journal_page_first              6418
_journal_paper_doi               10.1021/acs.chemmater.5b02601
_journal_volume                  27
_journal_year                    2015
_chemical_formula_moiety         C17H18S1O2N1Cl1
_chemical_formula_sum            'C34 H36 Cl2 N2 O4 S2'
_chemical_formula_weight         671.67
_chemical_name_common            DC-NDTI8
_chemical_name_systematic
; 
DCNDTI 
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                93.296(10)
_cell_angle_beta                 93.705(10)
_cell_angle_gamma                98.532(10)
_cell_formula_units_Z            1
_cell_length_a                   5.3741(11)
_cell_length_b                   8.3251(16)
_cell_length_c                   18.155(3)
_cell_measurement_temperature    100(2)
_cell_volume                     799.7(3)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12662
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         4.89
_exptl_absorpt_coefficient_mu    3.384
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_correction_T_min  0.7284
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2883
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0660
_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)+(0.1074P)²+0.1821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1725
_refine_ls_wR_factor_ref         0.2258
_reflns_number_gt                1653
_reflns_number_total             2883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm5b02601_si_002.cif
_cod_data_source_block           ydkr
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file
'/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4003188
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
S1A S 0.5115(5) 0.1727(3) 0.84406(9) 0.0574(6) Uani 0.769(4) 1 d PD A 1
C2A C 0.622(2) 0.3109(17) 0.9808(9) 0.0574(6) Uani 0.769(4) 1 d PD A 1
H2 H 0.7062 0.3805 1.0210 0.069 Uiso 0.769(4) 1 calc PR A 1
C2B C 0.490(7) 0.171(5) 0.8603(19) 0.075(3) Uani 0.231(4) 1 d PD A 2
H3 H 0.4830 0.1387 0.8091 0.090 Uiso 0.231(4) 1 calc PR A 2
S1B S 0.6737(16) 0.3336(14) 0.9880(8) 0.075(3) Uani 0.231(4) 1 d PD A 2
Cl1 Cl 0.9573(2) 0.41889(15) 0.87542(7) 0.0803(5) Uani 1 1 d . A .
O1 O -0.5376(6) -0.3339(4) 0.86949(15) 0.0744(9) Uani 1 1 d . . .
N1 N -0.1837(7) -0.2032(4) 0.82433(16) 0.0594(9) Uani 1 1 d . . .
O2 O 0.1464(6) -0.0544(4) 0.77707(14) 0.0694(8) Uani 1 1 d . . .
C5 C 0.1042(8) -0.0033(5) 0.9038(2) 0.0528(10) Uani 1 1 d . . .
C6 C -0.0411(7) -0.0409(5) 0.96449(19) 0.0496(9) Uani 1 1 d . . .
C3 C 0.3989(7) 0.1945(5) 0.9842(2) 0.0555(10) Uani 1 1 d D . .
C9 C 0.0278(8) -0.0861(5) 0.8305(2) 0.0564(10) Uani 1 1 d . . .
C10 C -0.2552(9) -0.2924(5) 0.7505(2) 0.0657(12) Uani 1 1 d . . .
H1 H -0.3617 -0.3974 0.7572 0.079 Uiso 1 1 calc R . .
H1A H -0.1005 -0.3164 0.7280 0.079 Uiso 1 1 calc R . .
C7 C -0.2598(8) -0.1573(5) 0.9555(2) 0.0537(10) Uani 1 1 d . . .
C8 C -0.3458(9) -0.2398(5) 0.8808(2) 0.0582(10) Uani 1 1 d . . .
C4 C 0.3174(7) 0.1118(5) 0.91304(19) 0.0540(10) Uani 1 1 d D A .
C1 C 0.6973(8) 0.3042(5) 0.9064(2) 0.0635(11) Uani 1 1 d . . .
C11 C -0.3974(9) -0.1960(6) 0.6982(2) 0.0768(14) Uani 1 1 d . . .
H1B H -0.5551 -0.1752 0.7198 0.092 Uiso 1 1 calc R . .
H1C H -0.2932 -0.0895 0.6927 0.092 Uiso 1 1 calc R . .
C13 C -0.6366(10) -0.2066(7) 0.5735(2) 0.0869(15) Uani 1 1 d . . .
H1G H -0.7950 -0.2020 0.5980 0.104 Uiso 1 1 calc R . .
H1F H -0.5584 -0.0932 0.5674 0.104 Uiso 1 1 calc R . .
C12 C -0.4610(10) -0.2840(6) 0.6234(2) 0.0828(15) Uani 1 1 d . . .
H1E H -0.5395 -0.3971 0.6299 0.099 Uiso 1 1 calc R . .
H1D H -0.3027 -0.2892 0.5990 0.099 Uiso 1 1 calc R . .
C15 C -0.8883(11) -0.2292(8) 0.4493(3) 0.109(2) Uani 1 1 d . . .
H1K H -0.8254 -0.1137 0.4420 0.131 Uiso 1 1 calc R . .
H1J H -1.0467 -0.2324 0.4745 0.131 Uiso 1 1 calc R . .
C14 C -0.7007(11) -0.2921(8) 0.4985(3) 0.1061(19) Uani 1 1 d . . .
H1I H -0.5430 -0.2886 0.4730 0.127 Uiso 1 1 calc R . .
H1H H -0.7638 -0.4079 0.5051 0.127 Uiso 1 1 calc R . .
C16 C -0.9492(14) -0.3216(10) 0.3728(4) 0.137(3) Uani 1 1 d . . .
H1M H -0.7938 -0.3096 0.3459 0.165 Uiso 1 1 calc R . .
H1L H -0.9964 -0.4388 0.3802 0.165 Uiso 1 1 calc R . .
C17 C -1.1473(14) -0.2706(9) 0.3269(4) 0.148(3) Uani 1 1 d . . .
H1N H -1.3035 -0.2831 0.3524 0.221 Uiso 1 1 calc R . .
H1P H -1.1738 -0.3379 0.2801 0.221 Uiso 1 1 calc R . .
H1O H -1.0997 -0.1562 0.3168 0.221 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C1 S1A C4 89.7(2) . . yes
C3 C2A C1 108.3(9) . . yes
C4 C2B C1 105(2) . . yes
C1 S1B C3 91.6(5) . . yes
C9 N1 C8 125.3(3) . . yes
C9 N1 C10 117.4(3) . . yes
C8 N1 C10 117.1(4) . . yes
C4 C5 C6 120.2(3) . . yes
C4 C5 C9 119.5(4) . . yes
C6 C5 C9 120.3(4) . . yes
C7 C6 C5 120.5(3) . . yes
C7 C6 C6 120.7(4) . 2_557 yes
C5 C6 C6 118.8(5) . 2_557 yes
C7 C3 C2A 128.9(7) 2_557 . yes
C7 C3 C4 119.4(3) 2_557 . yes
C2A C3 C4 111.7(7) . . yes
C7 C3 S1B 124.5(6) 2_557 . yes
C2A C3 S1B 4.8(11) . . yes
C4 C3 S1B 116.1(5) . . yes
O2 C9 N1 120.8(4) . . yes
O2 C9 C5 121.8(4) . . yes
N1 C9 C5 117.4(3) . . yes
N1 C10 C11 112.4(4) . . yes
C3 C7 C6 119.9(3) 2_557 . yes
C3 C7 C8 119.9(4) 2_557 . yes
C6 C7 C8 120.2(4) . . yes
O1 C8 N1 121.4(4) . . yes
O1 C8 C7 122.7(4) . . yes
N1 C8 C7 115.8(4) . . yes
C5 C4 C2B 130.1(19) . . yes
C5 C4 C3 121.1(3) . . yes
C2B C4 C3 108.9(19) . . yes
C5 C4 S1A 125.5(3) . . yes
C2B C4 S1A 5(2) . . yes
C3 C4 S1A 113.4(3) . . yes
C2A C1 S1B 12.4(5) . . yes
C2A C1 C2B 106.0(9) . . yes
S1B C1 C2B 118.3(5) . . yes
C2A C1 S1A 116.9(4) . . yes
S1B C1 S1A 129.1(4) . . yes
C2B C1 S1A 10.9(5) . . yes
C2A C1 Cl1 125.6(5) . . yes
S1B C1 Cl1 113.3(3) . . yes
C2B C1 Cl1 128.4(6) . . yes
S1A C1 Cl1 117.6(2) . . yes
C12 C11 C10 112.0(4) . . yes
C14 C13 C12 114.8(5) . . yes
C11 C12 C13 114.1(4) . . yes
C14 C15 C16 115.3(5) . . yes
C15 C14 C13 117.1(5) . . yes
C17 C16 C15 115.8(6) . . 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
S1A C1 1.692(5) . yes
S1A C4 1.732(4) . yes
C2A C3 1.433(11) . yes
C2A C1 1.436(16) . yes
C2B C4 1.433(11) . yes
C2B C1 1.61(5) . yes
S1B C1 1.506(15) . yes
S1B C3 1.731(4) . yes
Cl1 C1 1.716(4) . yes
O1 C8 1.197(5) . yes
N1 C9 1.377(5) . yes
N1 C8 1.405(5) . yes
N1 C10 1.494(5) . yes
O2 C9 1.214(5) . yes
C5 C4 1.375(5) . yes
C5 C6 1.414(5) . yes
C5 C9 1.469(5) . yes
C6 C7 1.403(6) . yes
C6 C6 1.434(7) 2_557 yes
C3 C7 1.390(5) 2_557 yes
C3 C4 1.438(5) . yes
C10 C11 1.518(6) . yes
C7 C3 1.390(5) 2_557 yes
C7 C8 1.497(5) . yes
C11 C12 1.500(6) . yes
C13 C14 1.494(6) . yes
C13 C12 1.505(6) . yes
C15 C14 1.477(7) . yes
C15 C16 1.540(8) . yes
C16 C17 1.439(8) . 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_4
_geom_torsion_publ_flag
C4 C5 C6 C7 179.5(3) . . yes
C9 C5 C6 C7 -0.1(6) . . yes
C4 C5 C6 C6 -1.2(7) . 2_557 yes
C9 C5 C6 C6 179.2(4) . 2_557 yes
C1 C2A C3 C7 179.6(5) . 2_557 yes
C1 C2A C3 C4 -1.4(13) . . yes
C1 C2A C3 S1B 155(14) . . yes
C1 S1B C3 C7 -179.4(4) . 2_557 yes
C1 S1B C3 C2A -22(13) . . yes
C1 S1B C3 C4 1.9(8) . . yes
C8 N1 C9 O2 -174.5(4) . . yes
C10 N1 C9 O2 2.0(6) . . yes
C8 N1 C9 C5 6.1(6) . . yes
C10 N1 C9 C5 -177.5(4) . . yes
C4 C5 C9 O2 -0.9(6) . . yes
C6 C5 C9 O2 178.7(4) . . yes
C4 C5 C9 N1 178.5(4) . . yes
C6 C5 C9 N1 -1.9(6) . . yes
C9 N1 C10 C11 -80.9(5) . . yes
C8 N1 C10 C11 95.8(5) . . yes
C5 C6 C7 C3 179.1(4) . 2_557 yes
C6 C6 C7 C3 -0.1(7) 2_557 2_557 yes
C5 C6 C7 C8 -1.7(6) . . yes
C6 C6 C7 C8 179.0(4) 2_557 . yes
C9 N1 C8 O1 173.7(4) . . yes
C10 N1 C8 O1 -2.7(6) . . yes
C9 N1 C8 C7 -7.7(6) . . yes
C10 N1 C8 C7 175.8(3) . . yes
C3 C7 C8 O1 3.0(7) 2_557 . yes
C6 C7 C8 O1 -176.2(4) . . yes
C3 C7 C8 N1 -175.6(4) 2_557 . yes
C6 C7 C8 N1 5.3(6) . . yes
C6 C5 C4 C2B -179(2) . . yes
C9 C5 C4 C2B 1(2) . . yes
C6 C5 C4 C3 0.8(6) . . yes
C9 C5 C4 C3 -179.6(4) . . yes
C6 C5 C4 S1A -179.1(3) . . yes
C9 C5 C4 S1A 0.5(6) . . yes
C1 C2B C4 C5 179.9(7) . . yes
C1 C2B C4 C3 0(3) . . yes
C1 C2B C4 S1A -179(24) . . yes
C7 C3 C4 C5 0.0(6) 2_557 . yes
C2A C3 C4 C5 -179.1(8) . . yes
S1B C3 C4 C5 178.8(6) . . yes
C7 C3 C4 C2B 179.9(18) 2_557 . yes
C2A C3 C4 C2B 1(2) . . yes
S1B C3 C4 C2B -1.4(19) . . yes
C7 C3 C4 S1A 180.0(3) 2_557 . yes
C2A C3 C4 S1A 0.8(8) . . yes
S1B C3 C4 S1A -1.3(7) . . yes
C1 S1A C4 C5 179.9(4) . . yes
C1 S1A C4 C2B 1(22) . . yes
C1 S1A C4 C3 0.0(4) . . yes
C3 C2A C1 S1B -169(6) . . yes
C3 C2A C1 C2B 1.4(19) . . yes
C3 C2A C1 S1A 1.5(13) . . yes
C3 C2A C1 Cl1 -178.9(5) . . yes
C3 S1B C1 C2A 9(5) . . yes
C3 S1B C1 C2B -1.8(19) . . yes
C3 S1B C1 S1A -2.3(10) . . yes
C3 S1B C1 Cl1 179.9(4) . . yes
C4 C2B C1 C2A -1(3) . . yes
C4 C2B C1 S1B 1(3) . . yes
C4 C2B C1 S1A 179(10) . . yes
C4 C2B C1 Cl1 179.4(10) . . yes
C4 S1A C1 C2A -0.9(8) . . yes
C4 S1A C1 S1B 1.7(8) . . yes
C4 S1A C1 C2B 0(8) . . yes
C4 S1A C1 Cl1 179.5(3) . . yes
N1 C10 C11 C12 178.1(4) . . yes
C10 C11 C12 C13 170.9(4) . . yes
C14 C13 C12 C11 179.6(5) . . yes
C16 C15 C14 C13 -179.7(6) . . yes
C12 C13 C14 C15 175.2(5) . . yes
C14 C15 C16 C17 174.8(6) . . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132574897
