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#$Date: 2022-04-03 23:09:45 +0300 (Sun, 03 Apr 2022) $
#$Revision: 274253 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519397.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_4519397
loop_
_publ_author_name
'Gazdag, Tamás'
'Mayer, Péter J'
'Kalapos, Péter Pál'
'Holczbauer, Tamás'
'El Bakouri, Ouissam'
'London, Gábor'
_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/[σ²(Fo²)+(0.0425P)²+1.7212P] where P=(Fo²+2Fc²)/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 > 2σ(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_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_min   0.940
_shelx_estimated_absorpt_t_max   0.952
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 0.91016(5) -0.16102(14) 0.71866(4) 0.0323(2) Uani 1 1 d . . . . .
C1 C 0.82560(17) 0.0625(5) 0.68771(14) 0.0286(6) Uani 1 1 d . . . . .
H1 H 0.777163 0.093199 0.712388 0.034 Uiso 1 1 calc R U . . .
C2 C 0.83726(16) 0.1876(5) 0.62412(14) 0.0272(6) Uani 1 1 d . . . . .
C3 C 0.79694(16) 0.3883(5) 0.56999(13) 0.0273(6) Uani 1 1 d . . . . .
C4 C 0.72625(16) 0.5517(5) 0.55233(14) 0.0269(6) Uani 1 1 d . . . . .
C5 C 0.73767(17) 0.7047(5) 0.48360(14) 0.0295(6) Uani 1 1 d . . . . .
C6 C 0.68722(19) 0.9049(6) 0.44327(15) 0.0376(7) Uani 1 1 d . . . . .
H6 H 0.634548 0.964882 0.458129 0.045 Uiso 1 1 calc R U . . .
C7 C 0.7148(2) 1.0172(7) 0.38054(17) 0.0456(8) Uani 1 1 d . . . . .
H7 H 0.680991 1.155864 0.353118 0.055 Uiso 1 1 calc R U . . .
C8 C 0.7906(2) 0.9291(6) 0.35801(16) 0.0407(7) Uani 1 1 d . . . . .
H8 H 0.807893 1.005964 0.314842 0.049 Uiso 1 1 calc R U . . .
C9 C 0.84214(19) 0.7285(6) 0.39780(14) 0.0335(6) Uani 1 1 d . . . . .
H9 H 0.894176 0.667785 0.381948 0.040 Uiso 1 1 calc R U . . .
C10 C 0.81637(17) 0.6193(5) 0.46062(14) 0.0286(6) Uani 1 1 d . . . . .
C11 C 0.85540(16) 0.4184(5) 0.51486(13) 0.0260(5) Uani 1 1 d . . . . .
C12 C 0.92567(17) 0.2520(5) 0.53118(14) 0.0296(6) Uani 1 1 d . . . . .
H12 H 0.972076 0.235381 0.503415 0.035 Uiso 1 1 calc R U . . .
C13 C 0.91729(16) 0.1031(5) 0.59904(14) 0.0276(6) Uani 1 1 d . . . . .
C14 C 0.96253(17) -0.0842(5) 0.64464(14) 0.0296(6) Uani 1 1 d . . . . .
H14 H 1.016165 -0.163067 0.636921 0.036 Uiso 1 1 calc R U . . .
C15 C 0.65027(16) 0.5678(5) 0.59106(14) 0.0266(6) Uani 1 1 d . . . . .
C18 C 0.50614(18) 0.5797(6) 0.66484(15) 0.0351(6) Uani 1 1 d . . . . .
H18 H 0.457849 0.586140 0.690717 0.042 Uiso 0.5 1 calc R U P A 1
H18A H 0.454641 0.581996 0.686651 0.042 Uiso 0.5 1 calc R U P B 2
C16 C 0.6582(3) 0.5666(10) 0.6671(3) 0.0257(11) Uani 0.5 1 d . . P C 1
H16 H 0.715185 0.559659 0.696157 0.031 Uiso 0.5 1 calc R U P C 1
C17 C 0.5869(4) 0.5753(11) 0.7035(3) 0.0319(12) Uani 0.5 1 d . . P C 1
H17 H 0.595643 0.578062 0.756553 0.038 Uiso 0.5 1 calc R U P C 1
C19 C 0.4905(3) 0.5749(11) 0.5856(3) 0.0322(12) Uani 0.5 1 d . . P C 1
H19 H 0.432536 0.575016 0.558439 0.039 Uiso 0.5 1 calc R U P C 1
C20 C 0.5617(3) 0.5701(11) 0.5486(3) 0.0293(11) Uani 0.5 1 d . . P C 1
H20 H 0.552687 0.568412 0.495619 0.035 Uiso 0.5 1 calc R U P C 1
C16A C 0.6130(3) 0.8152(11) 0.6045(3) 0.0315(12) Uani 0.5 1 d . . P C 2
H16A H 0.636173 0.979620 0.588807 0.038 Uiso 0.5 1 calc R U P C 2
C17A C 0.5411(4) 0.8199(12) 0.6414(3) 0.0366(13) Uani 0.5 1 d . . P C 2
H17A H 0.515489 0.988842 0.650738 0.044 Uiso 0.5 1 calc R U P C 2
C19A C 0.5486(4) 0.3383(12) 0.6554(3) 0.0357(13) Uani 0.5 1 d . . P C 2
H19A H 0.528168 0.174463 0.673928 0.043 Uiso 0.5 1 calc R U P C 2
C20A C 0.6208(3) 0.3315(11) 0.6192(3) 0.0296(11) Uani 0.5 1 d . . P C 2
H20A H 0.649734 0.164553 0.613883 0.036 Uiso 0.5 1 calc R U P C 2
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'
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
C14 S1 C1 92.16(12) . . ?
C2 C1 S1 111.4(2) . . ?
C2 C1 H1 124.3 . . ?
S1 C1 H1 124.3 . . ?
C1 C2 C13 112.5(2) . . ?
C1 C2 C3 141.5(2) . . ?
C13 C2 C3 105.9(2) . . ?
C4 C3 C2 143.1(2) . . ?
C4 C3 C11 110.3(2) . . ?
C2 C3 C11 106.6(2) . . ?
C3 C4 C15 126.8(2) . . ?
C3 C4 C5 107.0(2) . . ?
C15 C4 C5 126.1(2) . . ?
C6 C5 C10 119.4(2) . . ?
C6 C5 C4 131.5(2) . . ?
C10 C5 C4 109.0(2) . . ?
C5 C6 C7 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C5 120.8(2) . . ?
C9 C10 C11 132.8(2) . . ?
C5 C10 C11 106.4(2) . . ?
C12 C11 C10 141.9(2) . . ?
C12 C11 C3 110.9(2) . . ?
C10 C11 C3 107.3(2) . . ?
C11 C12 C13 107.8(2) . . ?
C11 C12 H12 126.1 . . ?
C13 C12 H12 126.1 . . ?
C14 C13 C2 112.6(2) . . ?
C14 C13 C12 138.5(2) . . ?
C2 C13 C12 108.9(2) . . ?
C13 C14 S1 111.3(2) . . ?
C13 C14 H14 124.4 . . ?
S1 C14 H14 124.4 . . ?
C20A C15 C16A 120.1(3) . . ?
C16 C15 C20 116.8(3) . . ?
C16 C15 C4 122.7(3) . . ?
C20A C15 C4 118.3(3) . . ?
C16A C15 C4 121.5(3) . . ?
C20 C15 C4 120.4(3) . . ?
C19A C18 C17A 118.2(4) . . ?
C17 C18 C19 121.3(4) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C19A C18 H18A 120.9 . . ?
C17A C18 H18A 120.9 . . ?
C15 C16 C17 122.8(4) . . ?
C15 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C18 C17 C16 120.4(5) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C20 C19 C18 118.6(4) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C15 120.0(4) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C15 C16A C17A 119.3(5) . . ?
C15 C16A H16A 120.3 . . ?
C17A C16A H16A 120.3 . . ?
C16A C17A C18 121.0(5) . . ?
C16A C17A H17A 119.5 . . ?
C18 C17A H17A 119.5 . . ?
C18 C19A C20A 121.2(5) . . ?
C18 C19A H19A 119.4 . . ?
C20A C19A H19A 119.4 . . ?
C15 C20A C19A 119.9(5) . . ?
C15 C20A H20A 120.1 . . ?
C19A C20A H20A 120.1 . . ?
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 C14 1.727(3) . ?
S1 C1 1.732(3) . ?
C1 C2 1.349(4) . ?
C1 H1 0.9500 . ?
C2 C13 1.454(3) . ?
C2 C3 1.459(4) . ?
C3 C4 1.354(4) . ?
C3 C11 1.468(3) . ?
C4 C15 1.474(3) . ?
C4 C5 1.495(4) . ?
C5 C6 1.389(4) . ?
C5 C10 1.419(4) . ?
C6 C7 1.398(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.455(4) . ?
C11 C12 1.356(4) . ?
C12 C13 1.460(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.354(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.366(5) . ?
C15 C20A 1.380(6) . ?
C15 C16A 1.389(6) . ?
C15 C20 1.457(6) . ?
C18 C17 1.328(6) . ?
C18 C19A 1.385(6) . ?
C18 C17A 1.398(7) . ?
C18 C19 1.420(6) . ?
C18 H18 0.9500 . ?
C18 H18A 0.9500 . ?
C16 C17 1.384(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C19 C20 1.385(7) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C16A C17A 1.395(8) . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9500 . ?
C19A C20A 1.391(7) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
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
C14 S1 C1 C2 0.2(2) . . . . ?
S1 C1 C2 C13 -0.3(3) . . . . ?
S1 C1 C2 C3 -179.1(3) . . . . ?
C1 C2 C3 C4 -2.6(6) . . . . ?
C13 C2 C3 C4 178.6(3) . . . . ?
C1 C2 C3 C11 178.2(3) . . . . ?
C13 C2 C3 C11 -0.7(3) . . . . ?
C2 C3 C4 C15 -3.3(5) . . . . ?
C11 C3 C4 C15 176.0(2) . . . . ?
C2 C3 C4 C5 179.3(3) . . . . ?
C11 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 -177.2(3) . . . . ?
C15 C4 C5 C6 5.4(5) . . . . ?
C3 C4 C5 C10 1.6(3) . . . . ?
C15 C4 C5 C10 -175.9(2) . . . . ?
C10 C5 C6 C7 0.4(4) . . . . ?
C4 C5 C6 C7 179.0(3) . . . . ?
C5 C6 C7 C8 0.8(5) . . . . ?
C6 C7 C8 C9 -0.9(5) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C8 C9 C10 C5 1.5(4) . . . . ?
C8 C9 C10 C11 -177.8(3) . . . . ?
C6 C5 C10 C9 -1.5(4) . . . . ?
C4 C5 C10 C9 179.5(2) . . . . ?
C6 C5 C10 C11 177.9(2) . . . . ?
C4 C5 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 -1.0(6) . . . . ?
C5 C10 C11 C12 179.7(3) . . . . ?
C9 C10 C11 C3 179.5(3) . . . . ?
C5 C10 C11 C3 0.2(3) . . . . ?
C4 C3 C11 C12 -178.9(2) . . . . ?
C2 C3 C11 C12 0.7(3) . . . . ?
C4 C3 C11 C10 0.8(3) . . . . ?
C2 C3 C11 C10 -179.7(2) . . . . ?
C10 C11 C12 C13 -179.8(3) . . . . ?
C3 C11 C12 C13 -0.3(3) . . . . ?
C1 C2 C13 C14 0.4(3) . . . . ?
C3 C2 C13 C14 179.6(2) . . . . ?
C1 C2 C13 C12 -178.7(2) . . . . ?
C3 C2 C13 C12 0.5(3) . . . . ?
C11 C12 C13 C14 -178.9(3) . . . . ?
C11 C12 C13 C2 -0.1(3) . . . . ?
C2 C13 C14 S1 -0.3(3) . . . . ?
C12 C13 C14 S1 178.5(3) . . . . ?
C1 S1 C14 C13 0.1(2) . . . . ?
C3 C4 C15 C16 42.5(5) . . . . ?
C5 C4 C15 C16 -140.6(3) . . . . ?
C3 C4 C15 C20A -36.4(4) . . . . ?
C5 C4 C15 C20A 140.5(3) . . . . ?
C3 C4 C15 C16A 138.6(4) . . . . ?
C5 C4 C15 C16A -44.5(4) . . . . ?
C3 C4 C15 C20 -134.0(3) . . . . ?
C5 C4 C15 C20 42.9(4) . . . . ?
C20 C15 C16 C17 -1.8(6) . . . . ?
C4 C15 C16 C17 -178.4(4) . . . . ?
C19 C18 C17 C16 0.2(7) . . . . ?
C15 C16 C17 C18 1.4(8) . . . . ?
C17 C18 C19 C20 -1.1(7) . . . . ?
C18 C19 C20 C15 0.5(7) . . . . ?
C16 C15 C20 C19 0.9(6) . . . . ?
C4 C15 C20 C19 177.6(4) . . . . ?
C20A C15 C16A C17A -5.2(7) . . . . ?
C4 C15 C16A C17A 180.0(4) . . . . ?
C15 C16A C17A C18 -0.1(8) . . . . ?
C19A C18 C17A C16A 4.6(7) . . . . ?
C17A C18 C19A C20A -4.1(7) . . . . ?
C16A C15 C20A C19A 5.7(6) . . . . ?
C4 C15 C20A C19A -179.3(4) . . . . ?
C18 C19A C20A C15 -1.0(7) . . . . ?
