#------------------------------------------------------------------------------
#$Date: 2021-01-07 08:14:42 +0100 (jue 07 de ene de 2021) $
#$Revision: 260828 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/96/1559698.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_1559698
loop_
_publ_author_name
'Wei, Congyuan'
'Tang, Zhonghai'
'Zhang, Weifeng'
'Huang, Jianyao'
'Zhou, Yankai'
'Wang, Liping'
'Yu, Gui'
_publ_section_title
;
 Molecular engineering of (E)-1,2-bis(3-cyanothiophene-2-yl)ethene-based
 polymeric semiconductors for unipolar n-channel field-effect transistors
;
_journal_issue                   46
_journal_name_full               'Polymer Chemistry'
_journal_page_first              7340
_journal_page_last               7348
_journal_paper_doi               10.1039/D0PY01399D
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C12 H6 N2 S2'
_chemical_formula_sum            'C12 H6 N2 S2'
_chemical_formula_weight         242.31
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-06 deposited with the CCDC.	2020-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.2960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.82980(10)
_cell_length_b                   10.4270(2)
_cell_length_c                   13.8707(2)
_cell_measurement_reflns_used    4472
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.8370
_cell_measurement_theta_min      3.1860
_cell_volume                     551.54(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -65.00   0.50    0.50    --  -47.32-134.00 152.00  108
  2  ω   -119.00 -64.00   0.50    0.50    --  -47.32-135.00 -27.00  110
  3  ω   -100.00 -15.00   0.50    0.50    --  -47.32 134.00-140.00  170
  4  ω     22.00 101.00   0.50    0.50    --   47.32-135.00 -27.00  158
  5  ω     21.00 100.00   0.50    0.50    --   47.32-134.00 152.00  158
  6  ω   -124.00 -26.00   0.50    0.50    --  -99.00 135.00  38.00  196
  7  ω     31.00 125.00   0.50    0.50    --  103.25-135.00 -27.00  188
  8  ω     31.00 123.00   0.50    0.50    --  103.25-134.00 152.00  184
  9  ω     71.00 169.00   0.50    0.50    --  103.25 135.00  38.00  196
 10  ω   -119.00 -71.00   0.50    0.50    --  -47.32-125.00-180.00   96
 11  ω     33.00 119.00   0.50    0.50    --   47.32  57.00 -30.00  172
 12  ω   -168.00 -81.00   0.50    0.50    --  -99.00 -94.00 -90.00  174
 13  ω   -168.00 -86.00   0.50    0.50    --  -99.00 -30.00-150.00  164
 14  ω     31.00 120.00   0.50    0.50    --  103.25 -61.00 120.00  178
 15  ω     31.00 120.00   0.50    0.50    --  103.25 -61.00 -30.00  178
 16  ω     31.00 109.00   0.50    0.50    --  103.25 -94.00-180.00  156
 17  ω     25.00 119.00   0.50    0.50    --   47.32  77.00  60.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0224098000
_diffrn_orient_matrix_UB_12      0.1471201000
_diffrn_orient_matrix_UB_13      -0.0089911000
_diffrn_orient_matrix_UB_21      0.2248597000
_diffrn_orient_matrix_UB_22      0.0138292000
_diffrn_orient_matrix_UB_23      0.0973891000
_diffrn_orient_matrix_UB_31      0.3349976000
_diffrn_orient_matrix_UB_32      0.0006023000
_diffrn_orient_matrix_UB_33      -0.0535378000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5098
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.020
_diffrn_reflns_theta_min         5.315
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       prism
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.167
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0362
_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)+(0.0609P)²+0.2559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0997
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1073
_reflns_number_total             1098
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0py01399d2.cif
_cod_data_source_block           tx104
_cod_depositor_comments
'Adding full bibliography for 1559697--1559698.cif.'
_cod_database_code               1559698
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHNOS
_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.
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5)
;
_shelx_res_file
;
TITL tx104_a.res in P2(1)/c
    tx104.res
    created by SHELXL-2017/1 at 11:10:45 on 15-Nov-2018
CELL 1.54184 3.8298 10.427 13.8707 90 95.296 90
ZERR 2 0.0001 0.0002 0.0002 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N S
UNIT 24 12 4 4

L.S. 4
PLAN  5
BOND
LIST 6
conf
htab
fmap 2
acta
OMIT -4 1 9
REM <olex2.extras>
REM <HklSrc "%.\\TX104.hkl">
REM </olex2.extras>

WGHT    0.060900    0.255900
FVAR       0.96569
S1    4    0.306502    0.631294    0.316486    11.00000    0.02980    0.02393 =
         0.02193   -0.00401   -0.00082   -0.00263
N1    3    0.954445    0.866886    0.596971    11.00000    0.04525    0.03035 =
         0.02979   -0.00426   -0.00479   -0.00627
C1    1    0.369774    0.786990    0.282073    11.00000    0.03725    0.02683 =
         0.02405    0.00274   -0.00049    0.00039
AFIX  43
H1    2    0.295755    0.819189    0.221065    11.00000   -1.20000
AFIX   0
C2    1    0.540140    0.858032    0.353915    11.00000    0.03697    0.02247 =
         0.02701    0.00204    0.00163   -0.00122
AFIX  43
H2    2    0.596699    0.944243    0.348034    11.00000   -1.20000
AFIX   0
C3    1    0.620761    0.784397    0.438832    11.00000    0.02693    0.02151 =
         0.02200   -0.00249    0.00258   -0.00160
C4    1    0.510846    0.658168    0.430394    11.00000    0.02249    0.02215 =
         0.02130   -0.00307    0.00144   -0.00060
C5    1    0.557073    0.560600    0.504723    11.00000    0.02496    0.02410 =
         0.02208   -0.00247    0.00060   -0.00063
AFIX  43
H5    2    0.675358    0.583895    0.563695    11.00000   -1.20000
AFIX   0
C6    1    0.805583    0.832380    0.526282    11.00000    0.03257    0.01912 =
         0.02689   -0.00062    0.00295   -0.00296
HKLF 4




REM  tx104_a.res in P2(1)/c
REM R1 =  0.0362 for    1073 Fo > 4sig(Fo)  and  0.0384 for all    1098 data
REM     73 parameters refined using      0 restraints

END

WGHT      0.0609      0.2559

REM Instructions for potential hydrogen bonds
EQIV $2 -x+2, -y+2, -z+1
HTAB C2 N1_$2

REM Highest difference peak  0.322,  deepest hole -0.534,  1-sigma level  0.099
Q1    1   0.0526  0.6129  0.3289  11.00000  0.05    0.32
Q2    1   1.3938  0.8233  0.5981  11.00000  0.05    0.31
Q3    1  -0.0422  0.6595  0.3117  11.00000  0.05    0.25
Q4    1   1.2167  0.8760  0.5982  11.00000  0.05    0.25
Q5    1   0.7301  0.7598  0.6694  11.00000  0.05    0.22
;
_shelx_res_checksum              36706
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.852
_oxdiff_exptl_absorpt_empirical_full_min 0.182
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_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
S1 S 0.30650(10) 0.63129(4) 0.31649(3) 0.0254(2) Uani 1 1 d . . . . .
N1 N 0.9544(5) 0.86689(14) 0.59697(13) 0.0356(4) Uani 1 1 d . . . . .
C1 C 0.3698(5) 0.78699(17) 0.28207(13) 0.0296(4) Uani 1 1 d . . . . .
H1 H 0.295755 0.819189 0.221065 0.035 Uiso 1 1 calc R . . . .
C2 C 0.5401(5) 0.85803(16) 0.35392(14) 0.0289(4) Uani 1 1 d . . . . .
H2 H 0.596699 0.944243 0.348034 0.035 Uiso 1 1 calc R . . . .
C3 C 0.6208(4) 0.78440(15) 0.43883(11) 0.0235(4) Uani 1 1 d . . . . .
C4 C 0.5108(4) 0.65817(16) 0.43039(12) 0.0220(4) Uani 1 1 d . . . . .
C5 C 0.5571(4) 0.56060(16) 0.50472(12) 0.0238(4) Uani 1 1 d . . . . .
H5 H 0.675358 0.583895 0.563695 0.029 Uiso 1 1 calc R . . . .
C6 C 0.8056(5) 0.83238(16) 0.52628(13) 0.0262(4) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0298(3) 0.0239(3) 0.0219(3) -0.00401(13) -0.00082(19) -0.00263(13)
N1 0.0453(10) 0.0304(9) 0.0298(9) -0.0043(6) -0.0048(8) -0.0063(6)
C1 0.0372(9) 0.0268(9) 0.0241(8) 0.0027(6) -0.0005(7) 0.0004(7)
C2 0.0370(10) 0.0225(8) 0.0270(9) 0.0020(6) 0.0016(8) -0.0012(6)
C3 0.0269(8) 0.0215(8) 0.0220(8) -0.0025(6) 0.0026(6) -0.0016(6)
C4 0.0225(7) 0.0222(8) 0.0213(8) -0.0031(6) 0.0014(6) -0.0006(6)
C5 0.0250(8) 0.0241(8) 0.0221(8) -0.0025(6) 0.0006(6) -0.0006(6)
C6 0.0326(9) 0.0191(8) 0.0269(9) -0.0006(6) 0.0029(7) -0.0030(6)
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'
S S 0.3331 0.5567 '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 S1 C4 92.15(8) . . ?
C2 C1 S1 112.48(13) . . ?
C1 C2 C3 111.56(15) . . ?
C2 C3 C6 124.48(15) . . ?
C4 C3 C2 113.84(15) . . ?
C4 C3 C6 121.67(15) . . ?
C3 C4 S1 109.98(12) . . ?
C3 C4 C5 126.30(15) . . ?
C5 C4 S1 123.71(13) . . ?
C5 C5 C4 125.2(2) 3_666 . ?
N1 C6 C3 177.92(18) . . ?
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 C1 1.7156(18) . ?
S1 C4 1.7202(16) . ?
N1 C6 1.146(2) . ?
C1 C2 1.359(3) . ?
C2 C3 1.416(2) . ?
C3 C4 1.384(2) . ?
C3 C6 1.437(2) . ?
C4 C5 1.448(2) . ?
C5 C5 1.340(3) 3_666 ?
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
S1 C1 C2 C3 -0.1(2) . . . . ?
S1 C4 C5 C5 -1.3(3) . . . 3_666 ?
C1 S1 C4 C3 0.00(13) . . . . ?
C1 S1 C4 C5 -179.88(15) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C2 C3 C6 178.83(16) . . . . ?
C2 C3 C4 S1 0.0(2) . . . . ?
C2 C3 C4 C5 179.84(16) . . . . ?
C3 C4 C5 C5 178.8(2) . . . 3_666 ?
C4 S1 C1 C2 0.03(15) . . . . ?
C6 C3 C4 S1 -178.84(13) . . . . ?
C6 C3 C4 C5 1.0(3) . . . . ?
