Synthesis, crystal structures and semiconductor properties of 2-(thiopyran-4-ylidene)-1,3-benzodithioles with an aryl substituent
Nishimoto, Hiroshi; Kawase, Takeshi; Nishida, Jun-ichi; CrystEngComm 25 (2023) 4856–4863; doi:10.1039/D3CE00416C

data_7247111
_publ_section_title
;
 Synthesis, crystal structures and semiconductor properties of
 2-(thiopyran-4-ylidene)-1,3-benzodithioles with an aryl substituent
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              4856
_journal_page_last               4863
_journal_paper_doi               10.1039/D3CE00416C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C17 H11 N S3'
_chemical_formula_sum            'C17 H11 N S3'
_chemical_formula_weight         325.45
_chemical_name_common            4Py-TP-BT
_chemical_name_systematic
5-(4-pyridyl)-2-(thiopyran-4-ylidene)-1,3-benzodithiole
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-04 deposited with the CCDC.	2023-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1579(3)
_cell_length_b                   7.5864(4)
_cell_length_c                   31.1475(14)
_cell_measurement_reflns_used    2392
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.0280
_cell_measurement_theta_min      2.9640
_cell_volume                     1455.10(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_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_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -24.00   2.00   0.50   18.00    --   20.00  54.00  90.00   52
  2  \w    -74.00 -48.00   0.50   18.00    --   20.00  54.00-150.00   52
  3  \w     10.00 108.00   0.50   18.00    --   20.00  54.00-150.00  196
  4  \w    -74.00  44.00   0.50   18.00    --   20.00  54.00   0.00  236
  5  \w    -42.00 -17.00   0.50   18.00    --   20.00  54.00  60.00   50
  6  \w     34.00  62.00   0.50   18.00    --   20.00  54.00  60.00   56
  7  \w     65.00  90.00   0.50   18.00    --   20.00  54.00  60.00   50
  8  \w    -56.00 -31.00   0.50   18.00    --   20.00  54.00  90.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0094481000
_diffrn_orient_matrix_UB_12      0.0216743000
_diffrn_orient_matrix_UB_13      -0.0220654000
_diffrn_orient_matrix_UB_21      0.1099172000
_diffrn_orient_matrix_UB_22      -0.0245813000
_diffrn_orient_matrix_UB_23      -0.0032841000
_diffrn_orient_matrix_UB_31      -0.0332063000
_diffrn_orient_matrix_UB_32      -0.0875673000
_diffrn_orient_matrix_UB_33      -0.0045468000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_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       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            9443
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.408
_diffrn_reflns_theta_min         2.616
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 636 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.37(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0553
_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/[\s^2^(Fo^2^)+(0.0528P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.564
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.758
_reflns_number_gt                2305
_reflns_number_total             3875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00416c2.cif
_cod_data_source_block           220711nishimoto4py-b
_cod_depositor_comments
'Adding full bibliography for 7247110--7247111.cif.'
_cod_database_code               7247111
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C17H11S3N1
_diffrn_oxdiff_digest_frames
;
013cd3fa7c7290f2cbb8bb500171d0601500025036a
;
_diffrn_oxdiff_digest_hkl
;
016d504e7fe6bdac2ba9744aa6700e7ad07a41
;
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C8(H8), C11(H11), C2(H2), C4(H4), C14(H14), C17(H17), C1(H1),
 C16(H16), C15(H15), C5(H5)
;
_olex2_submission_original_sample_id 220711nishimoto4Py-b
_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 1.101
_oxdiff_exptl_absorpt_empirical_full_min 0.924