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#$Date: 2020-06-09 01:28:09 +0300 (Tue, 09 Jun 2020) $
#$Revision: 253012 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/35/4003572.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_4003572
loop_
_publ_author_name
'Yamaguchi, Yuji'
'Kojiguchi, Yuka'
'Kawata, So'
'Mori, Tatsuya'
'Okamoto, Kazuo'
'Tsutsui, Masanori'
'Koganezawa, Tomoyuki'
'Katagiri, Hiroshi'
'Yasuda, Takuma'
_publ_section_title
;
 Solution-Processable Organic Semiconductors Featuring S-Shaped
 Dinaphthothienothiophene (S-DNTT): Effects of Alkyl Chain Length on
 Self-Organization and Carrier Transport Properties
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.0c01740
_journal_year                    2020
_chemical_formula_sum            'C34 H36 S2'
_chemical_formula_weight         508.75
_chemical_name_common            S-DNTT-6
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                82.946(9)
_cell_angle_beta                 77.081(8)
_cell_angle_gamma                80.005(6)
_cell_formula_units_Z            1
_cell_length_a                   7.2092(4)
_cell_length_b                   8.5332(8)
_cell_length_c                   11.1656(14)
_cell_measurement_reflns_used    2662
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.0710
_cell_measurement_theta_min      2.8940
_cell_volume                     656.80(11)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8713
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.941
_exptl_absorpt_coefficient_mu    0.225
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1009P)²+0.2332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1613
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2035
_reflns_number_total             2306
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm0c01740_si_003.cif
_cod_data_source_block           S-DNTT-6
_cod_database_code               4003572
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.75702(8) -0.08830(7) 0.05796(6) 0.0216(3) Uani 1 1 d . . . . .
C002 C 0.5061(3) 0.1756(3) 0.0770(2) 0.0195(6) Uani 1 1 d . . . . .
C003 C 0.1825(4) 1.0402(3) 0.3493(2) 0.0227(6) Uani 1 1 d . . . . .
H6 H 0.178914 1.109209 0.271500 0.027 Uiso 1 1 calc R U . . .
H7 H 0.047791 1.034075 0.392395 0.027 Uiso 1 1 calc R U . . .
C004 C 0.1803(4) 0.8001(3) 0.2378(2) 0.0236(6) Uani 1 1 d . . . . .
H8 H 0.046608 0.794383 0.283265 0.028 Uiso 1 1 calc R U . . .
H9 H 0.172865 0.873635 0.162605 0.028 Uiso 1 1 calc R U . . .
C005 C 0.2690(4) 0.6367(3) 0.1983(2) 0.0219(6) Uani 1 1 d . . . . .
C006 C 0.4236(3) 0.3300(3) 0.1154(2) 0.0198(5) Uani 1 1 d . . . . .
C007 C 0.5231(3) 0.4059(3) 0.1823(2) 0.0208(6) Uani 1 1 d . . . . .
C008 C 0.6798(3) 0.1014(3) 0.1092(2) 0.0220(6) Uani 1 1 d . . . . .
C009 C 0.7785(4) 0.1774(3) 0.1758(2) 0.0236(6) Uani 1 1 d . . . . .
H1 H 0.896668 0.125574 0.195964 0.028 Uiso 1 1 calc R U . . .
C00A C 0.4414(3) 0.0725(3) 0.0092(2) 0.0194(5) Uani 1 1 d . . . . .
C00B C 0.2818(4) 0.8733(3) 0.3179(2) 0.0242(6) Uani 1 1 d . . . . .
H10 H 0.416351 0.878749 0.274160 0.029 Uiso 1 1 calc R U . . .
H11 H 0.285260 0.803520 0.395347 0.029 Uiso 1 1 calc R U . . .
C00C C 0.4434(4) 0.5585(3) 0.2216(2) 0.0237(6) Uani 1 1 d . . . . .
H2 H 0.511706 0.609095 0.265491 0.028 Uiso 1 1 calc R U . . .
C00D C 0.1709(4) 0.5576(3) 0.1333(2) 0.0232(6) Uani 1 1 d . . . . .
H3 H 0.049534 0.608428 0.117563 0.028 Uiso 1 1 calc R U . . .
C00E C 0.2441(4) 0.4115(3) 0.0926(2) 0.0228(6) Uani 1 1 d . . . . .
H4 H 0.174282 0.363152 0.048265 0.027 Uiso 1 1 calc R U . . .
C00F C 0.2787(4) 1.1178(3) 0.4292(2) 0.0247(6) Uani 1 1 d . . . . .
H12 H 0.413554 1.123898 0.386514 0.030 Uiso 1 1 calc R U . . .
H13 H 0.281226 1.049747 0.507510 0.030 Uiso 1 1 calc R U . . .
C00G C 0.7014(4) 0.3256(3) 0.2106(2) 0.0253(6) Uani 1 1 d . . . . .
H5 H 0.767607 0.377448 0.254957 0.030 Uiso 1 1 calc R U . . .
C00H C 0.1771(4) 1.2849(3) 0.4583(2) 0.0259(6) Uani 1 1 d . . . . .
H14 H 0.175312 1.352987 0.379989 0.031 Uiso 1 1 calc R U . . .
H15 H 0.041933 1.278746 0.500423 0.031 Uiso 1 1 calc R U . . .
C00I C 0.2722(4) 1.3625(4) 0.5391(3) 0.0369(7) Uani 1 1 d . . . . .
H16 H 0.276728 1.294714 0.616241 0.055 Uiso 1 1 calc R U . . .
H17 H 0.197912 1.467368 0.557594 0.055 Uiso 1 1 calc R U . . .
H18 H 0.403478 1.375403 0.495714 0.055 Uiso 1 1 calc R U . . .
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
C00A S001 C008 91.11(11) 2_655 . ?
C008 C002 C006 119.3(2) . . ?
C008 C002 C00A 109.6(2) . . ?
C006 C002 C00A 131.2(2) . . ?
C00F C003 C00B 114.1(2) . . ?
C00F C003 H6 108.7 . . ?
C00B C003 H6 108.7 . . ?
C00F C003 H7 108.7 . . ?
C00B C003 H7 108.7 . . ?
H6 C003 H7 107.6 . . ?
C005 C004 C00B 116.9(2) . . ?
C005 C004 H8 108.1 . . ?
C00B C004 H8 108.1 . . ?
C005 C004 H9 108.1 . . ?
C00B C004 H9 108.1 . . ?
H8 C004 H9 107.3 . . ?
C00C C005 C00D 117.5(2) . . ?
C00C C005 C004 123.5(2) . . ?
C00D C005 C004 119.0(2) . . ?
C007 C006 C00E 117.9(2) . . ?
C007 C006 C002 118.7(2) . . ?
C00E C006 C002 123.5(2) . . ?
C00C C007 C006 119.5(2) . . ?
C00C C007 C00G 120.9(2) . . ?
C006 C007 C00G 119.6(2) . . ?
C002 C008 C009 121.9(2) . . ?
C002 C008 S001 113.17(19) . . ?
C009 C008 S001 125.0(2) . . ?
C00G C009 C008 118.8(2) . . ?
C00G C009 H1 120.6 . . ?
C008 C009 H1 120.6 . . ?
C00A C00A C002 115.1(3) 2_655 . ?
C00A C00A S001 111.0(2) 2_655 2_655 ?
C002 C00A S001 133.83(19) . 2_655 ?
C004 C00B C003 112.3(2) . . ?
C004 C00B H10 109.1 . . ?
C003 C00B H10 109.1 . . ?
C004 C00B H11 109.1 . . ?
C003 C00B H11 109.1 . . ?
H10 C00B H11 107.9 . . ?
C005 C00C C007 122.0(2) . . ?
C005 C00C H2 119.0 . . ?
C007 C00C H2 119.0 . . ?
C00E C00D C005 122.3(2) . . ?
C00E C00D H3 118.9 . . ?
C005 C00D H3 118.9 . . ?
C00D C00E C006 120.9(2) . . ?
C00D C00E H4 119.6 . . ?
C006 C00E H4 119.6 . . ?
C003 C00F C00H 112.9(2) . . ?
C003 C00F H12 109.0 . . ?
C00H C00F H12 109.0 . . ?
C003 C00F H13 109.0 . . ?
C00H C00F H13 109.0 . . ?
H12 C00F H13 107.8 . . ?
C009 C00G C007 121.8(2) . . ?
C009 C00G H5 119.1 . . ?
C007 C00G H5 119.1 . . ?
C00I C00H C00F 113.1(2) . . ?
C00I C00H H14 109.0 . . ?
C00F C00H H14 109.0 . . ?
C00I C00H H15 109.0 . . ?
C00F C00H H15 109.0 . . ?
H14 C00H H15 107.8 . . ?
C00H C00I H16 109.5 . . ?
C00H C00I H17 109.5 . . ?
H16 C00I H17 109.5 . . ?
C00H C00I H18 109.5 . . ?
H16 C00I H18 109.5 . . ?
H17 C00I H18 109.5 . . ?
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
S001 C00A 1.736(2) 2_655 ?
S001 C008 1.740(3) . ?
C002 C008 1.403(3) . ?
C002 C006 1.424(3) . ?
C002 C00A 1.425(3) . ?
C003 C00F 1.515(4) . ?
C003 C00B 1.523(3) . ?
C003 H6 0.9900 . ?
C003 H7 0.9900 . ?
C004 C005 1.504(3) . ?
C004 C00B 1.522(4) . ?
C004 H8 0.9900 . ?
C004 H9 0.9900 . ?
C005 C00C 1.381(4) . ?
C005 C00D 1.413(4) . ?
C006 C007 1.418(4) . ?
C006 C00E 1.419(3) . ?
C007 C00C 1.410(3) . ?
C007 C00G 1.430(3) . ?
C008 C009 1.412(4) . ?
C009 C00G 1.356(4) . ?
C009 H1 0.9500 . ?
C00A C00A 1.381(5) 2_655 ?
C00B H10 0.9900 . ?
C00B H11 0.9900 . ?
C00C H2 0.9500 . ?
C00D C00E 1.358(3) . ?
C00D H3 0.9500 . ?
C00E H4 0.9500 . ?
C00F C00H 1.523(3) . ?
C00F H12 0.9900 . ?
C00F H13 0.9900 . ?
C00G H5 0.9500 . ?
C00H C00I 1.518(4) . ?
C00H H14 0.9900 . ?
C00H H15 0.9900 . ?
C00I H16 0.9800 . ?
C00I H17 0.9800 . ?
C00I H18 0.9800 . ?
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
C00B C004 C005 C00C -6.0(4) . . . . ?
C00B C004 C005 C00D 174.3(2) . . . . ?
C008 C002 C006 C007 1.7(4) . . . . ?
C00A C002 C006 C007 -179.6(2) . . . . ?
C008 C002 C006 C00E -176.9(2) . . . . ?
C00A C002 C006 C00E 1.8(4) . . . . ?
C00E C006 C007 C00C -1.1(4) . . . . ?
C002 C006 C007 C00C -179.7(2) . . . . ?
C00E C006 C007 C00G 178.0(2) . . . . ?
C002 C006 C007 C00G -0.7(4) . . . . ?
C006 C002 C008 C009 -1.8(4) . . . . ?
C00A C002 C008 C009 179.2(2) . . . . ?
C006 C002 C008 S001 178.58(18) . . . . ?
C00A C002 C008 S001 -0.4(3) . . . . ?
C00A S001 C008 C002 0.4(2) 2_655 . . . ?
C00A S001 C008 C009 -179.2(2) 2_655 . . . ?
C002 C008 C009 C00G 0.7(4) . . . . ?
S001 C008 C009 C00G -179.72(19) . . . . ?
C008 C002 C00A C00A 0.1(4) . . . 2_655 ?
C006 C002 C00A C00A -178.7(3) . . . 2_655 ?
C008 C002 C00A S001 -179.6(2) . . . 2_655 ?
C006 C002 C00A S001 1.5(4) . . . 2_655 ?
C005 C004 C00B C003 178.4(2) . . . . ?
C00F C003 C00B C004 179.9(2) . . . . ?
C00D C005 C00C C007 0.3(4) . . . . ?
C004 C005 C00C C007 -179.5(2) . . . . ?
C006 C007 C00C C005 0.8(4) . . . . ?
C00G C007 C00C C005 -178.3(2) . . . . ?
C00C C005 C00D C00E -1.1(4) . . . . ?
C004 C005 C00D C00E 178.6(2) . . . . ?
C005 C00D C00E C006 0.9(4) . . . . ?
C007 C006 C00E C00D 0.3(4) . . . . ?
C002 C006 C00E C00D 178.9(2) . . . . ?
C00B C003 C00F C00H 179.6(2) . . . . ?
C008 C009 C00G C007 0.4(4) . . . . ?
C00C C007 C00G C009 178.6(2) . . . . ?
C006 C007 C00G C009 -0.4(4) . . . . ?
C003 C00F C00H C00I 179.6(2) . . . . ?
