#------------------------------------------------------------------------------
#$Date: 2021-04-04 13:00:40 +0300 (Sun, 04 Apr 2021) $
#$Revision: 263593 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/38/4003885.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_4003885
loop_
_publ_author_name
'Iguchi, Keitaro'
'Mikie, Tsubasa'
'Saito, Masahiko'
'Komeyama, Kimihiro'
'Seo, Takuji'
'Ie, Yutaka'
'Osaka, Itaru'
_publ_section_title
;
 N-type Semiconducting Polymers Based on Dicyano Naphthobisthiadiazole:
 High Electron Mobility with Unfavorable Backbone Twist
;
_journal_issue                   6
_journal_name_full               'Chemistry of Materials'
_journal_page_first              2218
_journal_page_last               2228
_journal_paper_doi               10.1021/acs.chemmater.1c00204
_journal_volume                  33
_journal_year                    2021
_chemical_formula_sum            'C30 H32 N4 S4'
_chemical_formula_weight         576.83
_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
_cell_angle_alpha                108.7050(10)
_cell_angle_beta                 94.5380(10)
_cell_angle_gamma                97.2580(10)
_cell_formula_units_Z            2
_cell_length_a                   4.6536(5)
_cell_length_b                   16.9349(16)
_cell_length_c                   18.5594(18)
_cell_measurement_reflns_used    6131
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.8504
_cell_measurement_theta_min      2.3283
_cell_volume                     1363.1(2)
_computing_cell_refinement       'APEX3 v2018.1-0 (Bruker AXS)'
_computing_data_collection       'APEX2(Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XSHELL V6.3.1(Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16369
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.01
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.303
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0421P)²+0.4451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                4850
_reflns_number_total             6470
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm1c00204_si_003.cif
_cod_data_source_block           20201201_NTz2T_Hex
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4003884--4003885.cif.
;
_cod_database_code               4003885
loop_
_space_group_symop_operation_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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2020(4) 0.91377(11) 0.88005(9) 0.0114(3) Uani d . . . 1 . .
C C2 -0.0006(4) 0.89452(11) 0.92922(9) 0.0119(3) Uani d . . . 1 . .
C C3 0.0713(4) 1.04093(10) 1.00617(9) 0.0110(3) Uani d . . . 1 . .
C C4 0.2735(4) 1.05940(11) 0.95789(9) 0.0117(3) Uani d . . . 1 . .
H H4 0.362458 1.116429 0.969378 0.014 Uiso calc U . R 1 . .
C C5 0.3472(4) 0.99918(11) 0.89548(9) 0.0113(3) Uani d . . . 1 . .
C C6 0.5568(4) 1.02007(10) 0.84727(9) 0.0114(3) Uani d . . . 1 . .
C C7 0.6629(4) 0.96778(11) 0.78579(9) 0.0125(4) Uani d . . . 1 . .
H H7 0.606415 0.908167 0.767589 0.015 Uiso calc U . R 1 . .
C C8 0.8655(4) 1.01058(11) 0.75151(10) 0.0136(4) Uani d . . . 1 . .
C C9 0.9110(4) 1.09544(11) 0.78884(10) 0.0157(4) Uani d . . . 1 . .
H H9 1.039719 1.134533 0.774679 0.019 Uiso calc U . R 1 . .
C C10 0.9942(4) 0.96597(12) 0.68038(10) 0.0166(4) Uani d . . . 1 . .
H H10A 1.063864 0.915123 0.685996 0.02 Uiso calc U . R 1 . .
H H10B 1.16439 1.003845 0.674552 0.02 Uiso calc U . R 1 . .
C C11 0.7710(4) 0.93984(12) 0.60855(10) 0.0165(4) Uani d . . . 1 . .
H H11A 0.599554 0.903143 0.615356 0.02 Uiso calc U . R 1 . .
H H11B 0.70374 0.99105 0.603108 0.02 Uiso calc U . R 1 . .
C C12 0.8887(4) 0.89307(12) 0.53487(10) 0.0181(4) Uani d . . . 1 . .
H H12A 1.061084 0.929376 0.527967 0.022 Uiso calc U . R 1 . .
H H12B 0.953321 0.841284 0.53969 0.022 Uiso calc U . R 1 . .
C C13 0.6619(4) 0.86884(12) 0.46431(10) 0.0189(4) Uani d . . . 1 . .
H H13A 0.492779 0.831115 0.470878 0.023 Uiso calc U . R 1 . .
H H13B 0.59178 0.920582 0.461126 0.023 Uiso calc U . R 1 . .
C C14 0.7731(4) 0.82487(12) 0.38916(10) 0.0194(4) Uani d . . . 1 . .
H H14A 0.950107 0.860659 0.38387 0.023 Uiso calc U . R 1 . .
H H14B 0.829072 0.770791 0.3904 0.023 Uiso calc U . R 1 . .
C C15 0.5469(4) 0.80743(12) 0.31988(10) 0.0206(4) Uani d . . . 1 . .
H H15A 0.368317 0.773868 0.325742 0.031 Uiso calc U . R 1 . .
H H15B 0.624126 0.776117 0.273312 0.031 Uiso calc U . R 1 . .
H H15C 0.502584 0.861053 0.315924 0.031 Uiso calc U . R 1 . .
C C16 1.7325(4) 0.40775(11) 0.38905(9) 0.0115(3) Uani d . . . 1 . .
C C17 1.5271(4) 0.39162(11) 0.43889(9) 0.0115(3) Uani d . . . 1 . .
C C18 1.4371(4) 0.45922(10) 0.49717(9) 0.0107(3) Uani d . . . 1 . .
C C19 1.2310(4) 0.44390(11) 0.54589(9) 0.0115(3) Uani d . . . 1 . .
H H19 1.152674 0.386978 0.538917 0.014 Uiso calc U . R 1 . .
C C20 1.1389(4) 0.50697(11) 0.60253(9) 0.0111(3) Uani d . . . 1 . .
C C21 0.9269(4) 0.48904(10) 0.65166(9) 0.0107(3) Uani d . . . 1 . .
C C22 0.8059(4) 0.54411(11) 0.70792(9) 0.0127(4) Uani d . . . 1 . .
H H22 0.849268 0.603681 0.720626 0.015 Uiso calc U . R 1 . .
C C23 0.6091(4) 0.50426(11) 0.74580(9) 0.0127(4) Uani d . . . 1 . .
C C24 0.5813(4) 0.41869(11) 0.71604(10) 0.0147(4) Uani d . . . 1 . .
H H24 0.458432 0.381237 0.733427 0.018 Uiso calc U . R 1 . .
C C25 0.4624(4) 0.55260(12) 0.81192(10) 0.0155(4) Uani d . . . 1 . .
H H25A 0.289058 0.515372 0.817084 0.019 Uiso calc U . R 1 . .
H H25B 0.394219 0.600988 0.800725 0.019 Uiso calc U . R 1 . .
C C26 0.6656(4) 0.58543(11) 0.88789(9) 0.0143(4) Uani d . . . 1 . .
H H26A 0.843993 0.620092 0.881844 0.017 Uiso calc U . R 1 . .
H H26B 0.725184 0.536826 0.900491 0.017 Uiso calc U . R 1 . .
C C27 0.5226(4) 0.63846(11) 0.95415(10) 0.0164(4) Uani d . . . 1 . .
H H27A 0.350094 0.602705 0.961706 0.02 Uiso calc U . R 1 . .
H H27B 0.452694 0.685002 0.940001 0.02 Uiso calc U . R 1 . .
C C28 0.7252(4) 0.67607(11) 1.02979(10) 0.0172(4) Uani d . . . 1 . .
H H28A 0.908113 0.706122 1.020688 0.021 Uiso calc U . R 1 . .
H H28B 0.631093 0.718294 1.066429 0.021 Uiso calc U . R 1 . .
C C29 0.8024(4) 0.61128(12) 1.06647(10) 0.0193(4) Uani d . . . 1 . .
H H29A 0.620165 0.580634 1.075269 0.023 Uiso calc U . R 1 . .
H H29B 0.900465 0.569555 1.030516 0.023 Uiso calc U . R 1 . .
C C30 1.0009(5) 0.65140(13) 1.14228(11) 0.0252(5) Uani d . . . 1 . .
H H30A 1.184552 0.680222 1.133675 0.038 Uiso calc U . R 1 . .
H H30B 1.041745 0.607435 1.163627 0.038 Uiso calc U . R 1 . .
H H30C 0.904204 0.692361 1.178339 0.038 Uiso calc U . R 1 . .
N N1 0.2322(3) 0.84517(9) 0.82127(8) 0.0158(3) Uani d . . . 1 . .
N N2 -0.1161(4) 0.81255(9) 0.90733(8) 0.0177(3) Uani d . . . 1 . .
N N3 1.7824(3) 0.33644(9) 0.33677(8) 0.0157(3) Uani d . . . 1 . .
N N4 1.4306(3) 0.30931(9) 0.42425(8) 0.0161(3) Uani d . . . 1 . .
S S1 0.02187(12) 0.76597(3) 0.83051(3) 0.02188(13) Uani d . . . 1 . .
S S2 0.71090(10) 1.12433(3) 0.86435(3) 0.01500(11) Uani d . . . 1 . .
S S3 1.58689(11) 0.25857(3) 0.35228(3) 0.02041(12) Uani d . . . 1 . .
S S4 0.79264(10) 0.38560(3) 0.64354(3) 0.01466(11) Uani d . . . 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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 112.66(15) ?
N1 C1 C5 . . 126.48(15) ?
C2 C1 C5 . . 120.86(15) ?
N2 C2 C3 . 2_577 124.73(15) ?
N2 C2 C1 . . 113.61(15) ?
C3 C2 C1 2_577 . 121.64(15) ?
C3 C3 C4 2_577 . 122.44(19) ?
C3 C3 C2 2_577 2_577 115.65(18) ?
C4 C3 C2 . 2_577 121.91(15) ?
C5 C4 C3 . . 123.58(16) ?
C5 C4 H4 . . 118.2 ?
C3 C4 H4 . . 118.2 ?
C4 C5 C1 . . 115.81(15) ?
C4 C5 C6 . . 122.29(16) ?
C1 C5 C6 . . 121.90(15) ?
C7 C6 C5 . . 129.54(16) ?
C7 C6 S2 . . 109.94(13) ?
C5 C6 S2 . . 120.53(13) ?
C6 C7 C8 . . 114.26(16) ?
C6 C7 H7 . . 122.9 ?
C8 C7 H7 . . 122.9 ?
C9 C8 C7 . . 111.16(16) ?
C9 C8 C10 . . 125.69(16) ?
C7 C8 C10 . . 123.06(16) ?
C8 C9 S2 . . 112.80(13) ?
C8 C9 H9 . . 123.6 ?
S2 C9 H9 . . 123.6 ?
C8 C10 C11 . . 111.67(15) ?
C8 C10 H10A . . 109.3 ?
C11 C10 H10A . . 109.3 ?
C8 C10 H10B . . 109.3 ?
C11 C10 H10B . . 109.3 ?
H10A C10 H10B . . 107.9 ?
C12 C11 C10 . . 113.86(15) ?
C12 C11 H11A . . 108.8 ?
C10 C11 H11A . . 108.8 ?
C12 C11 H11B . . 108.8 ?
C10 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
C13 C12 C11 . . 112.48(16) ?
C13 C12 H12A . . 109.1 ?
C11 C12 H12A . . 109.1 ?
C13 C12 H12B . . 109.1 ?
C11 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.8 ?
C14 C13 C12 . . 114.29(16) ?
C14 C13 H13A . . 108.7 ?
C12 C13 H13A . . 108.7 ?
C14 C13 H13B . . 108.7 ?
C12 C13 H13B . . 108.7 ?
H13A C13 H13B . . 107.6 ?
C15 C14 C13 . . 112.53(16) ?
C15 C14 H14A . . 109.1 ?
C13 C14 H14A . . 109.1 ?
C15 C14 H14B . . 109.1 ?
C13 C14 H14B . . 109.1 ?
H14A C14 H14B . . 107.8 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N3 C16 C17 . . 112.59(15) ?
N3 C16 C20 . 2_866 126.42(15) ?
C17 C16 C20 . 2_866 120.99(15) ?
N4 C17 C18 . . 124.82(15) ?
N4 C17 C16 . . 113.69(15) ?
C18 C17 C16 . . 121.48(15) ?
C18 C18 C19 2_866 . 122.28(19) ?
C18 C18 C17 2_866 . 115.86(19) ?
C19 C18 C17 . . 121.86(15) ?
C20 C19 C18 . . 123.67(16) ?
C20 C19 H19 . . 118.2 ?
C18 C19 H19 . . 118.2 ?
C19 C20 C16 . 2_866 115.70(15) ?
C19 C20 C21 . . 122.29(16) ?
C16 C20 C21 2_866 . 122.01(15) ?
C22 C21 C20 . . 129.30(16) ?
C22 C21 S4 . . 109.98(13) ?
C20 C21 S4 . . 120.72(13) ?
C21 C22 C23 . . 114.22(16) ?
C21 C22 H22 . . 122.9 ?
C23 C22 H22 . . 122.9 ?
C24 C23 C22 . . 111.24(15) ?
C24 C23 C25 . . 125.48(16) ?
C22 C23 C25 . . 123.25(16) ?
C23 C24 S4 . . 112.74(13) ?
C23 C24 H24 . . 123.6 ?
S4 C24 H24 . . 123.6 ?
C23 C25 C26 . . 112.57(15) ?
C23 C25 H25A . . 109.1 ?
C26 C25 H25A . . 109.1 ?
C23 C25 H25B . . 109.1 ?
C26 C25 H25B . . 109.1 ?
H25A C25 H25B . . 107.8 ?
C25 C26 C27 . . 112.64(15) ?
C25 C26 H26A . . 109.1 ?
C27 C26 H26A . . 109.1 ?
C25 C26 H26B . . 109.1 ?
C27 C26 H26B . . 109.1 ?
H26A C26 H26B . . 107.8 ?
C26 C27 C28 . . 113.88(15) ?
C26 C27 H27A . . 108.8 ?
C28 C27 H27A . . 108.8 ?
C26 C27 H27B . . 108.8 ?
C28 C27 H27B . . 108.8 ?
H27A C27 H27B . . 107.7 ?
C29 C28 C27 . . 114.33(15) ?
C29 C28 H28A . . 108.7 ?
C27 C28 H28A . . 108.7 ?
C29 C28 H28B . . 108.7 ?
C27 C28 H28B . . 108.7 ?
H28A C28 H28B . . 107.6 ?
C30 C29 C28 . . 112.71(16) ?
C30 C29 H29A . . 109.1 ?
C28 C29 H29A . . 109.0 ?
C30 C29 H29B . . 109.0 ?
C28 C29 H29B . . 109.1 ?
H29A C29 H29B . . 107.8 ?
C29 C30 H30A . . 109.5 ?
C29 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C29 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
C1 N1 S1 . . 106.56(12) ?
C2 N2 S1 . . 106.34(12) ?
C16 N3 S3 . . 106.70(12) ?
C17 N4 S3 . . 106.28(12) ?
N2 S1 N1 . . 100.82(8) ?
C9 S2 C6 . . 91.84(9) ?
N4 S3 N3 . . 100.73(8) ?
C24 S4 C21 . . 91.81(8) ?
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
C1 N1 . 1.346(2) ?
C1 C2 . 1.441(2) ?
C1 C5 . 1.445(2) ?
C2 N2 . 1.340(2) ?
C2 C3 2_577 1.433(2) ?
C3 C3 2_577 1.398(3) ?
C3 C4 . 1.423(2) ?
C4 C5 . 1.376(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.460(2) ?
C6 C7 . 1.372(2) ?
C6 S2 . 1.7370(17) ?
C7 C8 . 1.427(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.361(2) ?
C8 C10 . 1.507(2) ?
C9 S2 . 1.7182(18) ?
C9 H9 . 0.95 ?
C10 C11 . 1.529(2) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.527(2) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.525(3) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.521(2) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.521(3) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 N3 . 1.345(2) ?
C16 C17 . 1.442(2) ?
C16 C20 2_866 1.446(2) ?
C17 N4 . 1.341(2) ?
C17 C18 . 1.433(2) ?
C18 C18 2_866 1.398(3) ?
C18 C19 . 1.425(2) ?
C19 C20 . 1.377(2) ?
C19 H19 . 0.95 ?
C20 C21 . 1.464(2) ?
C21 C22 . 1.370(2) ?
C21 S4 . 1.7380(17) ?
C22 C23 . 1.428(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.360(2) ?
C23 C25 . 1.507(2) ?
C24 S4 . 1.7194(18) ?
C24 H24 . 0.95 ?
C25 C26 . 1.531(2) ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C26 C27 . 1.528(2) ?
C26 H26A . 0.99 ?
C26 H26B . 0.99 ?
C27 C28 . 1.527(2) ?
C27 H27A . 0.99 ?
C27 H27B . 0.99 ?
C28 C29 . 1.529(2) ?
C28 H28A . 0.99 ?
C28 H28B . 0.99 ?
C29 C30 . 1.522(3) ?
C29 H29A . 0.99 ?
C29 H29B . 0.99 ?
C30 H30A . 0.98 ?
C30 H30B . 0.98 ?
C30 H30C . 0.98 ?
N1 S1 . 1.6213(15) ?
N2 S1 . 1.6183(15) ?
N3 S3 . 1.6223(15) ?
N4 S3 . 1.6208(15) ?
