Unsymmetrical Thienopentalenes: Synthesis, Optoelectronic Properties, and (Anti)aromaticity Analysis.
Gazdag, Tamás; Mayer, Péter J; Kalapos, Péter Pál; Holczbauer, Tamás; El Bakouri, Ouissam; London, Gábor; ACS omega 7 (2022) 8336–8349; doi:10.1021/acsomega.1c05618

data_4519397
_publ_section_title
;
 Unsymmetrical Thienopentalenes: Synthesis, Optoelectronic Properties, and
 (Anti)aromaticity Analysis.
;
_journal_issue                   10
_journal_name_full               'ACS omega'
_journal_page_first              8336
_journal_page_last               8349
_journal_paper_doi               10.1021/acsomega.1c05618
_journal_volume                  7
_journal_year                    2022
_chemical_formula_moiety         'C20 H12 S'
_chemical_formula_sum            'C20 H12 S'
_chemical_formula_weight         284.36
_chemical_melting_point          408
_chemical_name_systematic
;
4-Phenylbenzo[4,5]pentaleno[1,2-c]thiophene
;
_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     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.752(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5106(7)
_cell_length_b                   4.9274(2)
_cell_length_c                   18.1757(9)
_cell_measurement_reflns_used    35483
_cell_measurement_temperature    138(2)
_cell_measurement_theta_max      27.515
_cell_measurement_theta_min      3.07
_cell_volume                     1369.04(11)
_computing_cell_refinement
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_molecular_graphics
;
Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.

Olex2 1.3 (Dolomanov et al., 2009)
;
_computing_publication_material
;
C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008

Olex2 1.3 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL-2018/3 (Sheldrick, 2018)
;
_computing_structure_solution
;
  Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.
;
_diffrn_ambient_temperature      138(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       RAXIS-RAPID
_diffrn_radiation_detector       RX
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            36556
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         3.197
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.991885
_exptl_absorpt_correction_T_min  0.968289
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+1.7212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2308
_reflns_number_total             2486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c05618_si_001.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4519397
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.952
_shelx_res_checksum              25663
_shelx_hkl_checksum              53789