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#$Date: 2017-03-04 16:37:16 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193643 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/51/1545173.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_1545173
loop_
_publ_author_name
'Chaolumen, ?'
'Murata, Michihisa'
'Wakamiya, Atsushi'
'Murata, Yasujiro'
_publ_section_title
;
 Dithieno-Fused Polycyclic Aromatic Hydrocarbon with a Pyracylene Moiety:
 Strong Antiaromatic Contribution to the Electronic Structure.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              826
_journal_page_last               829
_journal_paper_doi               10.1021/acs.orglett.6b03819
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C28 H16 S2'
_chemical_formula_weight         416.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.5642(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6951(15)
_cell_length_b                   5.6063(9)
_cell_length_c                   17.751(3)
_cell_measurement_reflns_used    2459
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.37
_cell_volume                     933.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4121
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.042
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_min         2.196
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_transmission_factor_max   0.7455
_exptl_transmission_factor_min   0.5677
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0470
_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)+(0.0267P)²+1.1127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1352
_reflns_number_total             1645
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b03819_si_003.cif
_cod_data_source_block           5
_cod_depositor_comments          'Adding full bibliography for 1545173.cif.'
_cod_database_code               1545173
_shelx_shelxl_version_number     2014/7
_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   0.979
_shelx_estimated_absorpt_t_max   0.994
_exptl_absorpt_special_details
;
SADABS (Sheldrick, 1997)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C12A C 0.2437(8) 0.4434(15) 0.1136(4) 0.0283(17) Uani 0.808(4) 1 d . . P A 1
H12 H 0.2408 0.4093 0.1656 0.034 Uiso 0.808(4) 1 calc R U P A 1
C10 C 0.3071(3) 0.3995(4) -0.00310(14) 0.0226(6) Uani 1 1 d . . . . .
C6 C 0.4231(2) 0.1005(4) 0.08097(13) 0.0222(6) Uani 1 1 d . . . . .
C11 C 0.3250(2) 0.3070(4) 0.07186(14) 0.0228(6) Uani 1 1 d . . . . .
C8 C 0.3911(2) 0.2598(5) -0.04597(13) 0.0213(6) Uani 1 1 d . . . . .
C1 C 0.6358(3) -0.4284(5) 0.17837(14) 0.0259(6) Uani 1 1 d . . . . .
H1 H 0.6959 -0.5507 0.1676 0.030(7) Uiso 1 1 calc R . . . .
C4 C 0.4578(3) -0.0715(5) 0.21312(13) 0.0234(6) Uani 1 1 d . . . . .
H4 H 0.3983 0.0477 0.2263 0.021(7) Uiso 1 1 calc R . . . .
C13 C 0.1698(3) 0.6297(5) 0.07067(16) 0.0308(7) Uani 1 1 d . . . . .
C7 C 0.4562(2) 0.0858(4) 0.00820(13) 0.0213(6) Uani 1 1 d . . . . .
C5 C 0.4846(2) -0.0695(4) 0.13740(13) 0.0216(6) Uani 1 1 d . . . . .
C9 C 0.5792(2) -0.2558(5) 0.11947(13) 0.0217(6) Uani 1 1 d . . . . .
C2 C 0.6063(3) -0.4230(5) 0.24932(14) 0.0261(6) Uani 1 1 d . . . . .
H2 H 0.6457 -0.5402 0.2873 0.027(7) Uiso 1 1 calc R . . . .
C3 C 0.5162(3) -0.2412(5) 0.26661(14) 0.0288(6) Uani 1 1 d . . . . .
H3 H 0.4964 -0.2384 0.3164 0.038(8) Uiso 1 1 calc R . . . .
C14A C 0.0783(4) 0.8059(7) 0.0999(3) 0.0276(9) Uani 0.808(4) 1 d . . P A 1
H14 H 0.0802 0.7692 0.1541 0.041 Uiso 0.808(4) 1 calc R U P A 1
H14A H -0.0199 0.7958 0.0679 0.041 Uiso 0.808(4) 1 calc R U P A 1
H14B H 0.1149 0.9675 0.0967 0.041 Uiso 0.808(4) 1 calc R U P A 1
C12B C 0.219(8) 0.605(14) -0.014(4) 0.29(6) Uiso 0.192(4) 1 d . . P A 2
H15 H 0.1928 0.7048 -0.0585 0.349 Uiso 0.192(4) 1 calc R U P A 2
S1B S 0.2406(11) 0.4411(19) 0.1312(5) 0.025(2) Uiso 0.192(4) 1 d . . P A 2
C14B C 0.068(2) 0.846(4) 0.0729(10) 0.020(5) Uiso 0.192(4) 1 d . . P A 2
H16 H 0.0407 0.8454 0.1225 0.030 Uiso 0.192(4) 1 calc R U P A 2
H16A H -0.0183 0.8307 0.0300 0.030 Uiso 0.192(4) 1 calc R U P A 2
H16B H 0.1164 0.9952 0.0674 0.030 Uiso 0.192(4) 1 calc R U P A 2
S1A S 0.19749(9) 0.64127(16) -0.01950(5) 0.0220(4) Uani 0.808(4) 1 d . . P A 1
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
C13 C12A C11 113.2(5) . .
C11 C10 C12B 111(3) . .
C11 C10 C8 110.0(2) . .
C12B C10 C8 139(3) . .
C11 C10 S1A 112.41(19) . .
C8 C10 S1A 137.58(19) . .
C5 C6 C7 117.5(2) . .
C5 C6 C11 139.0(2) . .
C7 C6 C11 103.5(2) . .
C10 C11 C12A 110.0(4) . .
C10 C11 C6 108.5(2) . .
C12A C11 C6 141.6(4) . .
C10 C11 S1B 118.1(4) . .
C6 C11 S1B 133.4(4) . .
C7 C8 C9 117.6(2) . 3_655
C7 C8 C10 103.2(2) . .
C9 C8 C10 139.2(2) 3_655 .
C2 C1 C9 122.1(2) . .
C3 C4 C5 121.2(2) . .
C12A C13 C14A 125.1(4) . .
S1B C13 C14B 133.2(7) . .
C12A C13 S1A 111.6(4) . .
C14A C13 S1A 123.3(3) . .
S1B C13 C12B 113(3) . .
C14B C13 C12B 114(3) . .
C7 C7 C8 122.8(3) 3_655 .
C7 C7 C6 122.3(3) 3_655 .
C8 C7 C6 114.9(2) . .
C6 C5 C4 122.1(2) . .
C6 C5 C9 120.1(2) . .
C4 C5 C9 117.8(2) . .
C8 C9 C1 122.5(2) 3_655 .
C8 C9 C5 119.7(2) 3_655 .
C1 C9 C5 117.8(2) . .
C1 C2 C3 119.9(2) . .
C4 C3 C2 121.3(2) . .
C10 C12B C13 104(5) . .
C13 S1B C11 94.1(4) . .
C13 S1A C10 92.78(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C12A C13 1.382(8) .
C12A C11 1.432(8) .
C10 C11 1.398(3) .
C10 C12B 1.42(8) .
C10 C8 1.473(3) .
C10 S1A 1.701(3) .
C6 C5 1.402(3) .
C6 C7 1.409(3) .
C6 C11 1.482(4) .
C11 S1B 1.667(9) .
C8 C7 1.404(3) .
C8 C9 1.405(3) 3_655
C1 C2 1.360(3) .
C1 C9 1.429(3) .
C4 C3 1.363(4) .
C4 C5 1.432(3) .
C13 C14A 1.504(5) .
C13 S1B 1.540(10) .
C13 C14B 1.571(19) .
C13 S1A 1.689(3) .
C13 C12B 1.69(7) .
C7 C7 1.362(5) 3_655
C5 C9 1.477(4) .
C9 C8 1.405(3) 3_655
C2 C3 1.425(4) .
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_4
C8 C10 C11 C12A 179.8(4) . .
S1A C10 C11 C12A 0.5(4) . .
C12B C10 C11 C6 -177(3) . .
C8 C10 C11 C6 0.1(3) . .
S1A C10 C11 C6 -179.18(16) . .
C12B C10 C11 S1B 2(3) . .
C8 C10 C11 S1B 179.2(5) . .
C13 C12A C11 C10 -0.3(7) . .
C13 C12A C11 C6 179.1(3) . .
C5 C6 C11 C10 -179.4(3) . .
C7 C6 C11 C10 -0.3(3) . .
C5 C6 C11 C12A 1.1(7) . .
C7 C6 C11 C12A -179.8(6) . .
C5 C6 C11 S1B 1.7(7) . .
C7 C6 C11 S1B -179.1(6) . .
C11 C10 C8 C7 0.1(3) . .
C12B C10 C8 C7 177(4) . .
S1A C10 C8 C7 179.1(2) . .
C11 C10 C8 C9 -179.7(3) . 3_655
C12B C10 C8 C9 -3(4) . 3_655
S1A C10 C8 C9 -0.6(5) . 3_655
C11 C12A C13 C14A -178.6(4) . .
C11 C12A C13 S1A 0.1(7) . .
C9 C8 C7 C7 -1.0(4) 3_655 3_655
C10 C8 C7 C7 179.2(3) . 3_655
C9 C8 C7 C6 179.5(2) 3_655 .
C10 C8 C7 C6 -0.3(3) . .
C5 C6 C7 C7 0.2(4) . 3_655
C11 C6 C7 C7 -179.2(3) . 3_655
C5 C6 C7 C8 179.7(2) . .
C11 C6 C7 C8 0.4(3) . .
C7 C6 C5 C4 -179.8(2) . .
C11 C6 C5 C4 -0.7(4) . .
C7 C6 C5 C9 -0.4(3) . .
C11 C6 C5 C9 178.7(3) . .
C3 C4 C5 C6 178.6(2) . .
C3 C4 C5 C9 -0.8(3) . .
C2 C1 C9 C8 -179.9(2) . 3_655
C2 C1 C9 C5 -0.8(3) . .
C6 C5 C9 C8 0.9(3) . 3_655
C4 C5 C9 C8 -179.7(2) . 3_655
C6 C5 C9 C1 -178.3(2) . .
C4 C5 C9 C1 1.1(3) . .
C9 C1 C2 C3 0.1(4) . .
C5 C4 C3 C2 0.1(4) . .
C1 C2 C3 C4 0.2(4) . .
C11 C10 C12B C13 -3(4) . .
C8 C10 C12B C13 -179.3(3) . .
S1B C13 C12B C10 3(5) . .
C14B C13 C12B C10 -179(3) . .
C14B C13 S1B C11 -179.1(11) . .
C12B C13 S1B C11 -2(3) . .
C10 C11 S1B C13 0.6(7) . .
C6 C11 S1B C13 179.4(3) . .
C12A C13 S1A C10 0.2(4) . .
C14A C13 S1A C10 178.9(3) . .
C11 C10 S1A C13 -0.4(2) . .
C8 C10 S1A C13 -179.4(3) . .
