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#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/46/4024630.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_4024630
loop_
_publ_author_name
'Agostino Pietrangelo'
'Brian O. Patrick'
'Mark J. MacLachlan'
'Michael O. Wolf'
_publ_section_title
;
Conjugated Thiophene-Containing Oligoacenes Through Photocyclization: Bent
Acenedithiophenes and a Thiahelicene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4918
_journal_page_last               4926
_journal_paper_doi               10.1021/jo900590u
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C18 H14 O2 S2'
_chemical_formula_weight         326.41
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.627(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.008(2)
_cell_length_b                   11.9600(10)
_cell_length_c                   7.8922(7)
_cell_measurement_reflns_used    2689
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.47
_cell_volume                     1557.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7750
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.62(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0536P)²+0.5159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                2908
_reflns_number_total             3371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900590u_si_002.cif
_cod_data_source_block           mw061
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4024630
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2425(2) 0.1571(3) 0.8240(4) 0.0420(7) Uani 1 1 d . . .
C2 C -0.2423(2) 0.0596(3) 0.7311(5) 0.0406(8) Uani 1 1 d . . .
H2 H -0.2875 0.0137 0.6780 0.049 Uiso 1 1 calc R . .
C3 C -0.1675(2) 0.0370(2) 0.7250(4) 0.0410(7) Uani 1 1 d . . .
H3 H -0.1587 -0.0237 0.6617 0.049 Uiso 1 1 calc R . .
C4 C -0.1080(2) 0.1121(2) 0.8205(4) 0.0354(6) Uani 1 1 d . . .
C5 C -0.02406(18) 0.1183(2) 0.8345(4) 0.0334(6) Uani 1 1 d . . .
C6 C 0.02305(19) 0.0222(2) 0.8490(4) 0.0334(6) Uani 1 1 d . . .
C7 C 0.09898(18) 0.0308(2) 0.8443(4) 0.0354(7) Uani 1 1 d . . .
H7 H 0.1283 -0.0342 0.8508 0.043 Uiso 1 1 calc R . .
C8 C 0.13293(18) 0.1332(2) 0.8302(4) 0.0338(6) Uani 1 1 d . . .
C9 C 0.08514(19) 0.2297(2) 0.8145(4) 0.0358(7) Uani 1 1 d . . .
C11 C -0.00319(18) -0.0900(2) 0.8845(4) 0.0409(7) Uani 1 1 d . . .
H11 H -0.0446 -0.0931 0.9266 0.049 Uiso 1 1 calc R . .
C12 C 0.1086(2) 0.3404(2) 0.7680(5) 0.0479(8) Uani 1 1 d . . .
H12 H 0.1460 0.3426 0.7140 0.058 Uiso 1 1 calc R . .
C10 C 0.0097(2) 0.2207(2) 0.8209(4) 0.0365(7) Uani 1 1 d . . .
H10 H -0.0195 0.2856 0.8161 0.044 Uiso 1 1 calc R . .
C13 C 0.21576(19) 0.1388(2) 0.8371(4) 0.0346(6) Uani 1 1 d . . .
C14 C 0.2725(2) 0.2200(2) 0.9080(5) 0.0432(8) Uani 1 1 d . . .
H14 H 0.2630 0.2853 0.9602 0.052 Uiso 1 1 calc R . .
C15 C 0.3474(3) 0.1970(3) 0.8960(5) 0.0417(8) Uani 1 1 d . . .
H15 H 0.3914 0.2454 0.9376 0.050 Uiso 1 1 calc R . .
C16 C 0.3477(2) 0.0947(3) 0.8159(4) 0.0410(7) Uani 1 1 d . . .
C17 C -0.3113(3) 0.2110(3) 0.8543(6) 0.0656(11) Uani 1 1 d . . .
H17A H -0.3334 0.2704 0.7665 0.098 Uiso 1 1 calc R . .
H17B H -0.2919 0.2409 0.9774 0.098 Uiso 1 1 calc R . .
H17C H -0.3526 0.1564 0.8386 0.098 Uiso 1 1 calc R . .
C18 C 0.4154(2) 0.0417(3) 0.7846(6) 0.0605(10) Uani 1 1 d . . .
H18A H 0.4562 0.0966 0.7978 0.091 Uiso 1 1 calc R . .
H18B H 0.3955 0.0108 0.6621 0.091 Uiso 1 1 calc R . .
H18C H 0.4383 -0.0169 0.8735 0.091 Uiso 1 1 calc R . .
O1 O 0.02502(17) -0.17641(19) 0.8630(4) 0.0606(7) Uani 1 1 d . . .
O2 O 0.08240(19) 0.4274(2) 0.7957(5) 0.0771(9) Uani 1 1 d . . .
S1 S -0.14739(4) 0.21567(7) 0.91272(9) 0.0431(2) Uani 1 1 d . . .
S2 S 0.25546(4) 0.02983(6) 0.75719(8) 0.0433(2) Uani 1 1 d . . .
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'
O O 0.0106 0.0060 '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
C2 C1 C17 128.9(4) . . ?
C2 C1 S1 110.3(3) . . ?
C17 C1 S1 120.8(3) . . ?
C1 C2 C3 113.0(3) . . ?
C1 C2 H2 123.5 . . ?
C3 C2 H2 123.5 . . ?
C4 C3 C2 114.1(3) . . ?
C4 C3 H3 123.0 . . ?
C2 C3 H3 123.0 . . ?
C3 C4 C5 128.8(3) . . ?
C3 C4 S1 109.8(3) . . ?
C5 C4 S1 121.0(2) . . ?
C10 C5 C6 117.3(3) . . ?
C10 C5 C4 120.4(2) . . ?
C6 C5 C4 122.2(2) . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 C11 117.7(2) . . ?
C5 C6 C11 121.8(3) . . ?
C6 C7 C8 122.5(2) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C7 C8 C9 116.9(3) . . ?
C7 C8 C13 120.5(2) . . ?
C9 C8 C13 122.5(2) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 C12 117.4(3) . . ?
C8 C9 C12 121.8(3) . . ?
O1 C11 C6 124.7(3) . . ?
O1 C11 H11 117.7 . . ?
C6 C11 H11 117.7 . . ?
O2 C12 C9 124.0(3) . . ?
O2 C12 H12 118.0 . . ?
C9 C12 H12 118.0 . . ?
C9 C10 C5 122.5(2) . . ?
C9 C10 H10 118.7 . . ?
C5 C10 H10 118.7 . . ?
C14 C13 C8 129.2(3) . . ?
C14 C13 S2 109.8(3) . . ?
C8 C13 S2 121.0(2) . . ?
C13 C14 C15 114.4(3) . . ?
C13 C14 H14 122.8 . . ?
C15 C14 H14 122.8 . . ?
C16 C15 C14 112.5(4) . . ?
C16 C15 H15 123.7 . . ?
C14 C15 H15 123.7 . . ?
C15 C16 C18 127.8(4) . . ?
C15 C16 S2 110.0(3) . . ?
C18 C16 S2 122.2(3) . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 S1 C4 92.67(17) . . ?
C16 S2 C13 93.29(16) . . ?
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
C1 C2 1.377(5) . ?
C1 C17 1.498(5) . ?
C1 S1 1.719(4) . ?
C2 C3 1.395(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.472(4) . ?
C4 S1 1.727(3) . ?
C5 C10 1.390(4) . ?
C5 C6 1.406(4) . ?
C6 C7 1.387(4) . ?
C6 C11 1.486(4) . ?
C7 C8 1.393(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.415(4) . ?
C8 C13 1.472(4) . ?
C9 C10 1.384(5) . ?
C9 C12 1.480(4) . ?
C11 O1 1.194(4) . ?
C11 H11 0.9300 . ?
C12 O2 1.198(4) . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C13 C14 1.357(4) . ?
C13 S2 1.723(3) . ?
C14 C15 1.416(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(5) . ?
C15 H15 0.9300 . ?
C16 C18 1.480(5) . ?
C16 S2 1.720(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
C17 C1 C2 C3 177.8(3) . . . . ?
S1 C1 C2 C3 -3.0(4) . . . . ?
C1 C2 C3 C4 3.4(4) . . . . ?
C2 C3 C4 C5 -176.0(3) . . . . ?
C2 C3 C4 S1 -2.1(3) . . . . ?
C3 C4 C5 C10 136.6(3) . . . . ?
S1 C4 C5 C10 -36.6(4) . . . . ?
C3 C4 C5 C6 -38.9(5) . . . . ?
S1 C4 C5 C6 147.8(2) . . . . ?
C10 C5 C6 C7 -1.8(4) . . . . ?
C4 C5 C6 C7 173.9(3) . . . . ?
C10 C5 C6 C11 173.3(3) . . . . ?
C4 C5 C6 C11 -11.0(4) . . . . ?
C5 C6 C7 C8 1.7(5) . . . . ?
C11 C6 C7 C8 -173.6(3) . . . . ?
C6 C7 C8 C9 -2.0(4) . . . . ?
C6 C7 C8 C13 176.2(3) . . . . ?
C7 C8 C9 C10 2.6(4) . . . . ?
C13 C8 C9 C10 -175.7(3) . . . . ?
C7 C8 C9 C12 -169.8(3) . . . . ?
C13 C8 C9 C12 12.0(4) . . . . ?
C7 C6 C11 O1 -20.1(5) . . . . ?
C5 C6 C11 O1 164.7(3) . . . . ?
C10 C9 C12 O2 26.0(5) . . . . ?
C8 C9 C12 O2 -161.4(4) . . . . ?
C8 C9 C10 C5 -2.9(5) . . . . ?
C12 C9 C10 C5 169.8(3) . . . . ?
C6 C5 C10 C9 2.5(4) . . . . ?
C4 C5 C10 C9 -173.3(3) . . . . ?
C7 C8 C13 C14 -146.5(3) . . . . ?
C9 C8 C13 C14 31.6(5) . . . . ?
C7 C8 C13 S2 30.4(4) . . . . ?
C9 C8 C13 S2 -151.5(2) . . . . ?
C8 C13 C14 C15 178.3(3) . . . . ?
S2 C13 C14 C15 1.2(4) . . . . ?
C13 C14 C15 C16 -0.8(5) . . . . ?
C14 C15 C16 C18 -178.4(3) . . . . ?
C14 C15 C16 S2 0.1(4) . . . . ?
C2 C1 S1 C4 1.5(3) . . . . ?
C17 C1 S1 C4 -179.2(3) . . . . ?
C3 C4 S1 C1 0.3(2) . . . . ?
C5 C4 S1 C1 174.7(2) . . . . ?
C15 C16 S2 C13 0.5(3) . . . . ?
C18 C16 S2 C13 179.1(3) . . . . ?
C14 C13 S2 C16 -1.0(2) . . . . ?
C8 C13 S2 C16 -178.4(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658981
