#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:44:07 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286123 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/71/7247110.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_7247110
loop_
_publ_author_name
'Nishimoto, Hiroshi'
'Kawase, Takeshi'
'Nishida, Jun-ichi'
_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            2Py-TP-BT
_chemical_name_systematic
5-(2-pyridyl)-2-(thiopyran-4-ylidene)-1,3-benzodithiole
_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             2022-04-19
_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                 94.692(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0602(12)
_cell_length_b                   7.6455(9)
_cell_length_c                   11.9152(13)
_cell_measurement_reflns_used    2655
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.9130
_cell_measurement_theta_min      2.5780
_cell_volume                     1458.1(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  69.00   0.50   25.62    --   20.00  54.00   0.00   52
  2  ω    -42.00  94.00   0.50   25.62    --   20.00  54.00-120.00  272
  3  ω     11.00  84.00   0.50   25.62    --   20.00  54.00-150.00  146
  4  ω    -72.00  67.00   0.50   25.62    --   20.00  54.00 150.00  278
  5  ω    -73.00   5.00   0.50   25.62    --   20.00  54.00  30.00  156
  6  ω     62.00  87.00   0.50   25.62    --   20.00  54.00  30.00   50
  7  ω    -16.00  84.00   0.50   25.62    --   20.00  54.00-180.00  200
  8  ω    -29.00  -4.00   0.50   25.62    --   20.00  54.00   0.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0338832000
_diffrn_orient_matrix_UB_12      0.0441128000
_diffrn_orient_matrix_UB_13      -0.0295490000
_diffrn_orient_matrix_UB_21      -0.0258418000
_diffrn_orient_matrix_UB_22      -0.0210013000
_diffrn_orient_matrix_UB_23      0.0436042000
_diffrn_orient_matrix_UB_31      0.0120574000
_diffrn_orient_matrix_UB_32      0.0789489000
_diffrn_orient_matrix_UB_33      0.0281342000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14545
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.341
_diffrn_reflns_theta_min         2.545
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70630
_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            'orangish yellow'
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0015(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0465
_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)+(0.0468P)²+0.2785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2758
_reflns_number_total             4229
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00416c2.cif
_cod_data_source_block           220418nishimotopy
_cod_depositor_comments
'Adding full bibliography for 7247110--7247111.cif.'
_cod_database_code               7247110
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C17H11S3N1
_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.
;
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.825
_diffrn_oxdiff_digest_frames
;
01f2a4ffc603345e1dc71d7265b6d8eeeb000256ec9
;
_diffrn_oxdiff_digest_hkl
;
0108e3f24f2a2b1307043c255d93c2b2a5bc37
;
_reflns_odcompleteness_completeness 99.97
_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:
 C9(H9), C12(H12), C11(H11), C4(H4), C2(H2), C5(H5), C1(H1), C14(H14),
 C15(H15), C17(H17), C16(H16)
;
_olex2_submission_original_sample_id Py-TP-BT
_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 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.852
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
S3 S 0.54841(3) 0.77331(7) 0.52841(4) 0.03373(15) Uani 1 1 d . . . . .
S2 S 0.50201(3) 0.54984(8) 0.71775(5) 0.03616(15) Uani 1 1 d . . . . .
S1 S 0.19327(3) 0.70527(11) 0.47041(6) 0.0597(2) Uani 1 1 d . . . . .
N1 N 0.90520(11) 0.8079(3) 0.79823(16) 0.0462(5) Uani 1 1 d . . . . .
C7 C 0.60719(11) 0.6126(3) 0.72017(16) 0.0287(4) Uani 1 1 d . . . . .
C8 C 0.62930(11) 0.7138(3) 0.62875(16) 0.0284(4) Uani 1 1 d . . . . .
C6 C 0.46824(12) 0.6632(3) 0.59297(16) 0.0288(4) Uani 1 1 d . . . . .
C3 C 0.38663(12) 0.6629(3) 0.54989(17) 0.0300(4) Uani 1 1 d . . . . .
C9 C 0.71226(12) 0.7636(3) 0.62141(17) 0.0317(4) Uani 1 1 d . . . . .
H9 H 0.727014 0.828717 0.560164 0.038 Uiso 1 1 calc R . . . .
C12 C 0.66795(12) 0.5628(3) 0.80405(16) 0.0333(5) Uani 1 1 d . . . . .
H12 H 0.653719 0.494398 0.864111 0.040 Uiso 1 1 calc R . . . .
C10 C 0.77319(11) 0.7153(3) 0.70640(17) 0.0322(5) Uani 1 1 d . . . . .
C11 C 0.74999(12) 0.6163(3) 0.79727(17) 0.0353(5) Uani 1 1 d . . . . .
H11 H 0.790295 0.585566 0.854363 0.042 Uiso 1 1 calc R . . . .
C4 C 0.36009(13) 0.7538(3) 0.44561(18) 0.0347(5) Uani 1 1 d . . . . .
H4 H 0.401385 0.799624 0.403795 0.042 Uiso 1 1 calc R . . . .
C13 C 0.86234(12) 0.7690(3) 0.69968(18) 0.0352(5) Uani 1 1 d . . . . .
C2 C 0.32290(12) 0.5673(3) 0.60651(18) 0.0376(5) Uani 1 1 d . . . . .
H2 H 0.340884 0.494274 0.666055 0.045 Uiso 1 1 calc R . . . .
C5 C 0.28073(13) 0.7760(3) 0.40593(19) 0.0412(5) Uani 1 1 d . . . . .
H5 H 0.271232 0.834538 0.337661 0.049 Uiso 1 1 calc R . . . .
C1 C 0.24056(13) 0.5779(3) 0.57843(19) 0.0452(6) Uani 1 1 d . . . . .
H1 H 0.205748 0.511389 0.620273 0.054 Uiso 1 1 calc R . . . .
C14 C 0.89881(14) 0.7752(3) 0.5974(2) 0.0458(6) Uani 1 1 d . . . . .
H14 H 0.867522 0.748914 0.530346 0.055 Uiso 1 1 calc R . . . .
C15 C 0.98213(15) 0.8211(4) 0.5970(2) 0.0580(7) Uani 1 1 d . . . . .
H15 H 1.007622 0.825350 0.529721 0.070 Uiso 1 1 calc R . . . .
C17 C 0.98597(14) 0.8533(4) 0.7944(2) 0.0563(7) Uani 1 1 d . . . . .
H17 H 1.016116 0.881873 0.861865 0.068 Uiso 1 1 calc R . . . .
C16 C 1.02693(15) 0.8604(4) 0.6975(3) 0.0617(8) Uani 1 1 d . . . . .
H16 H 1.083106 0.890830 0.699689 0.074 Uiso 1 1 calc R . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S3 C6 96.05(9) . . ?
C7 S2 C6 96.23(9) . . ?
C1 S1 C5 100.45(11) . . ?
C13 N1 C17 116.9(2) . . ?
C8 C7 S2 116.23(15) . . ?
C12 C7 S2 123.71(16) . . ?
C12 C7 C8 120.03(18) . . ?
C7 C8 S3 116.85(14) . . ?
C9 C8 S3 123.02(16) . . ?
C9 C8 C7 120.13(18) . . ?
S3 C6 S2 114.55(11) . . ?
C3 C6 S3 123.22(16) . . ?
C3 C6 S2 122.22(15) . . ?
C6 C3 C4 121.57(18) . . ?
C6 C3 C2 120.79(19) . . ?
C4 C3 C2 117.63(18) . . ?
C8 C9 C10 119.85(19) . . ?
C11 C12 C7 119.40(19) . . ?
C9 C10 C13 120.28(18) . . ?
C11 C10 C9 119.28(18) . . ?
C11 C10 C13 120.45(18) . . ?
C12 C11 C10 121.29(18) . . ?
C5 C4 C3 124.6(2) . . ?
N1 C13 C10 115.92(19) . . ?
N1 C13 C14 122.3(2) . . ?
C14 C13 C10 121.8(2) . . ?
C1 C2 C3 124.5(2) . . ?
C4 C5 S1 125.88(19) . . ?
C2 C1 S1 125.53(18) . . ?
C15 C14 C13 119.1(2) . . ?
C16 C15 C14 119.3(2) . . ?
N1 C17 C16 124.5(2) . . ?
C17 C16 C15 118.0(2) . . ?
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
S3 C8 1.752(2) . ?
S3 C6 1.7663(19) . ?
S2 C7 1.7540(19) . ?
S2 C6 1.768(2) . ?
S1 C5 1.741(2) . ?
S1 C1 1.739(2) . ?
N1 C13 1.345(3) . ?
N1 C17 1.347(3) . ?
C7 C8 1.405(3) . ?
C7 C12 1.391(3) . ?
C8 C9 1.395(3) . ?
C6 C3 1.368(3) . ?
C3 C4 1.457(3) . ?
C3 C2 1.466(3) . ?
C9 C10 1.399(3) . ?
C12 C11 1.388(3) . ?
C10 C11 1.396(3) . ?
C10 C13 1.498(3) . ?
C4 C5 1.334(3) . ?
C13 C14 1.396(3) . ?
C2 C1 1.340(3) . ?
C14 C15 1.384(3) . ?
C15 C16 1.379(4) . ?
C17 C16 1.376(3) . ?
