#------------------------------------------------------------------------------
#$Date: 2021-04-04 13:00:40 +0300 (Sun, 04 Apr 2021) $
#$Revision: 263593 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/38/4003884.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_4003884
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            'C32 H30 N6 S4'
_chemical_formula_weight         626.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 106.912(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.465(5)
_cell_length_b                   7.409(2)
_cell_length_c                   13.518(4)
_cell_measurement_reflns_used    9688
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      28.8552
_cell_measurement_theta_min      2.7543
_cell_volume                     1481.9(8)
_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      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0322
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16967
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.75
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.94
_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 orange'
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0365P)²+0.9361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                2987
_reflns_number_total             3548
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm1c00204_si_002.cif
_cod_data_source_block           20200129CN_NTz2T
_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               4003884
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.95509(10) 0.55277(19) 1.16572(11) 0.0201(3) Uani d . . . 1 . .
C C2 0.90685(9) 0.54275(19) 1.05813(11) 0.0194(3) Uani d . . . 1 . .
C C3 0.95314(9) 0.51387(19) 0.98113(11) 0.0188(3) Uani d . . . 1 . .
C C4 0.90616(10) 0.51120(19) 0.87138(11) 0.0200(3) Uani d . . . 1 . .
C C5 0.81269(10) 0.5681(2) 0.83697(11) 0.0238(3) Uani d . . . 1 . .
C C6 0.94833(10) 0.46795(19) 0.79660(11) 0.0201(3) Uani d . . . 1 . .
C C7 0.90037(10) 0.4458(2) 0.68654(11) 0.0209(3) Uani d . . . 1 . .
C C8 0.81369(10) 0.3866(2) 0.64125(11) 0.0232(3) Uani d . . . 1 . .
H H8 0.774731 0.348883 0.680172 0.028 Uiso calc U . R 1 . .
C C9 0.78704(10) 0.3864(2) 0.53125(11) 0.0229(3) Uani d . . . 1 . .
C C10 0.85536(10) 0.4486(2) 0.49520(11) 0.0261(3) Uani d . . . 1 . .
H H10 0.850102 0.462068 0.423798 0.031 Uiso calc U . R 1 . .
C C11 0.69625(10) 0.3224(2) 0.46525(11) 0.0267(3) Uani d . . . 1 . .
H H11A 0.648802 0.385709 0.487707 0.032 Uiso calc U . R 1 . .
H H11B 0.690795 0.191944 0.478065 0.032 Uiso calc U . R 1 . .
C C12 0.67789(10) 0.3511(2) 0.34933(11) 0.0264(3) Uani d . . . 1 . .
H H12A 0.675439 0.48215 0.334438 0.032 Uiso calc U . R 1 . .
H H12B 0.728122 0.298895 0.327038 0.032 Uiso calc U . R 1 . .
C C13 0.58919(11) 0.2638(2) 0.28811(12) 0.0293(3) Uani d . . . 1 . .
H H13A 0.596107 0.130994 0.293716 0.035 Uiso calc U . R 1 . .
H H13B 0.541505 0.298485 0.319954 0.035 Uiso calc U . R 1 . .
C C14 0.55824(11) 0.3148(3) 0.17438(12) 0.0308(4) Uani d . . . 1 . .
H H14A 0.55006 0.44729 0.168191 0.037 Uiso calc U . R 1 . .
H H14B 0.605777 0.281029 0.142106 0.037 Uiso calc U . R 1 . .
C C15 0.47026(12) 0.2229(3) 0.11634(14) 0.0407(4) Uani d . . . 1 . .
H H15A 0.480119 0.090764 0.119164 0.049 Uiso calc U . R 1 . .
H H15B 0.424432 0.249434 0.152434 0.049 Uiso calc U . R 1 . .
C C16 0.43272(14) 0.2788(3) 0.00413(15) 0.0513(5) Uani d . . . 1 . .
H H16A 0.416929 0.407198 0.000426 0.077 Uiso calc U . R 1 . .
H H16B 0.378604 0.207415 -0.028649 0.077 Uiso calc U . R 1 . .
H H16C 0.478351 0.257801 -0.031962 0.077 Uiso calc U . R 1 . .
N N1 0.90106(8) 0.58417(18) 1.22620(10) 0.0248(3) Uani d . . . 1 . .
N N2 0.81761(8) 0.56599(18) 1.03927(10) 0.0247(3) Uani d . . . 1 . .
N N3 0.74037(10) 0.6215(2) 0.80417(11) 0.0356(3) Uani d . . . 1 . .
S S1 0.79951(3) 0.59811(6) 1.14940(3) 0.02779(11) Uani d . . . 1 . .
S S2 0.95122(3) 0.49971(6) 0.59169(3) 0.02655(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 . . 113.17(13) ?
N1 C1 C6 . 3_767 124.48(13) ?
C2 C1 C6 . 3_767 122.35(13) ?
N2 C2 C1 . . 112.99(13) ?
N2 C2 C3 . . 125.63(13) ?
C1 C2 C3 . . 121.37(13) ?
C3 C3 C2 3_767 . 115.88(16) ?
C3 C3 C4 3_767 . 121.77(16) ?
C2 C3 C4 . . 122.35(13) ?
C6 C4 C5 . . 118.01(13) ?
C6 C4 C3 . . 123.07(13) ?
C5 C4 C3 . . 118.78(13) ?
N3 C5 C4 . . 174.70(17) ?
C4 C6 C1 . 3_767 115.16(13) ?
C4 C6 C7 . . 123.91(13) ?
C1 C6 C7 3_767 . 120.93(13) ?
C8 C7 C6 . . 128.93(13) ?
C8 C7 S2 . . 109.72(11) ?
C6 C7 S2 . . 121.34(11) ?
C7 C8 C9 . . 114.50(13) ?
C7 C8 H8 . . 122.7 ?
C9 C8 H8 . . 122.7 ?
C10 C9 C8 . . 110.70(13) ?
C10 C9 C11 . . 125.46(14) ?
C8 C9 C11 . . 123.83(14) ?
C9 C10 S2 . . 113.08(11) ?
C9 C10 H10 . . 123.5 ?
S2 C10 H10 . . 123.5 ?
C9 C11 C12 . . 115.37(13) ?
C9 C11 H11A . . 108.4 ?
C12 C11 H11A . . 108.4 ?
C9 C11 H11B . . 108.4 ?
C12 C11 H11B . . 108.4 ?
H11A C11 H11B . . 107.5 ?
C13 C12 C11 . . 111.60(13) ?
C13 C12 H12A . . 109.3 ?
C11 C12 H12A . . 109.3 ?
C13 C12 H12B . . 109.3 ?
C11 C12 H12B . . 109.3 ?
H12A C12 H12B . . 108.0 ?
C14 C13 C12 . . 114.37(14) ?
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 . . 112.47(14) ?
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 ?
C16 C15 C14 . . 114.79(16) ?
C16 C15 H15A . . 108.6 ?
C14 C15 H15A . . 108.6 ?
C16 C15 H15B . . 108.6 ?
C14 C15 H15B . . 108.6 ?
H15A C15 H15B . . 107.5 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C1 N1 S1 . . 106.24(10) ?
C2 N2 S1 . . 106.83(10) ?
N2 S1 N1 . . 100.77(7) ?
C10 S2 C7 . . 91.95(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 . 1.3485(18) ?
C1 C2 . 1.430(2) ?
C1 C6 3_767 1.439(2) ?
C2 N2 . 1.3396(19) ?
C2 C3 . 1.441(2) ?
C3 C3 3_767 1.405(3) ?
C3 C4 . 1.450(2) ?
C4 C6 . 1.391(2) ?
C4 C5 . 1.447(2) ?
C5 N3 . 1.147(2) ?
C6 C7 . 1.466(2) ?
C7 C8 . 1.374(2) ?
C7 S2 . 1.7346(15) ?
C8 C9 . 1.423(2) ?
C8 H8 . 0.95 ?
C9 C10 . 1.366(2) ?
C9 C11 . 1.504(2) ?
C10 S2 . 1.7081(16) ?
C10 H10 . 0.95 ?
C11 C12 . 1.524(2) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.525(2) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.519(2) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.520(2) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.516(2) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
N1 S1 . 1.6144(14) ?
N2 S1 . 1.6107(14) ?
