#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:12:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178425 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/46/4024632.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_4024632
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            'C30 H34 S2'
_chemical_formula_weight         458.69
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 91.264(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.9141(9)
_cell_length_b                   7.0287(9)
_cell_length_c                   22.219(3)
_cell_measurement_reflns_used    4344
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.57
_cell_volume                     1235.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12302
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yelloiw
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.4440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                2480
_reflns_number_total             2963
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900590u_si_004.cif
_cod_data_source_block           mw064
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024632
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.68064(18) 1.0330(2) 0.77170(6) 0.0244(3) Uani 1 1 d . . .
C2 C 0.70958(18) 1.2042(2) 0.79740(6) 0.0244(3) Uani 1 1 d . . .
H2 H 0.7558 1.3090 0.7764 0.029 Uiso 1 1 calc R . .
C3 C 0.66427(17) 1.21304(19) 0.85906(6) 0.0220(3) Uani 1 1 d . . .
C4 C 0.59996(17) 1.04246(19) 0.87916(6) 0.0208(3) Uani 1 1 d . . .
C5 C 0.68193(19) 1.36749(19) 0.89994(6) 0.0257(3) Uani 1 1 d . . .
H5 H 0.7263 1.4853 0.8865 0.031 Uiso 1 1 calc R . .
C6 C 0.63613(19) 1.34782(19) 0.95772(6) 0.0255(3) Uani 1 1 d . . .
H6 H 0.6502 1.4521 0.9846 0.031 Uiso 1 1 calc R . .
C7 C 0.56693(17) 1.17359(19) 0.97946(6) 0.0212(3) Uani 1 1 d . . .
C8 C 0.54827(17) 1.01469(19) 0.93966(6) 0.0206(3) Uani 1 1 d . . .
C9 C 0.48246(18) 0.84582(19) 0.96118(6) 0.0221(3) Uani 1 1 d . . .
H9 H 0.4708 0.7404 0.9347 0.026 Uiso 1 1 calc R . .
C10 C 0.7152(2) 0.9707(2) 0.70879(6) 0.0290(3) Uani 1 1 d . . .
H10A H 0.7977 1.0593 0.6911 0.035 Uiso 1 1 calc R . .
H10B H 0.6092 0.9795 0.6845 0.035 Uiso 1 1 calc R . .
C11 C 0.7833(2) 0.7702(2) 0.70437(6) 0.0288(3) Uani 1 1 d . . .
H11A H 0.6956 0.6797 0.7176 0.035 Uiso 1 1 calc R . .
H11B H 0.8823 0.7569 0.7321 0.035 Uiso 1 1 calc R . .
C12 C 0.8353(2) 0.7183(2) 0.64121(7) 0.0285(3) Uani 1 1 d . . .
H12A H 0.7399 0.7444 0.6128 0.034 Uiso 1 1 calc R . .
H12B H 0.9312 0.7999 0.6296 0.034 Uiso 1 1 calc R . .
C13 C 0.8864(2) 0.5114(2) 0.63568(7) 0.0299(3) Uani 1 1 d . . .
H13A H 0.9768 0.4836 0.6659 0.036 Uiso 1 1 calc R . .
H13B H 0.7881 0.4302 0.6449 0.036 Uiso 1 1 calc R . .
C14 C 0.9484(2) 0.4604(2) 0.57390(7) 0.0332(4) Uani 1 1 d . . .
H14A H 0.8597 0.4920 0.5434 0.040 Uiso 1 1 calc R . .
H14B H 1.0495 0.5378 0.5652 0.040 Uiso 1 1 calc R . .
C15 C 0.9927(3) 0.2520(3) 0.56874(9) 0.0515(5) Uani 1 1 d . . .
H15A H 1.0798 0.2197 0.5991 0.077 Uiso 1 1 calc R . .
H15B H 1.0355 0.2263 0.5285 0.077 Uiso 1 1 calc R . .
H15C H 0.8916 0.1749 0.5753 0.077 Uiso 1 1 calc R . .
S1 S 0.59466(5) 0.87498(5) 0.822547(15) 0.02482(11) 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'
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 C10 128.60(13) . . ?
C2 C1 S1 111.16(10) . . ?
C10 C1 S1 120.23(11) . . ?
C1 C2 C3 113.68(12) . . ?
C1 C2 H2 123.2 . . ?
C3 C2 H2 123.2 . . ?
C4 C3 C5 119.25(12) . . ?
C4 C3 C2 112.06(12) . . ?
C5 C3 C2 128.65(13) . . ?
C3 C4 C8 122.61(12) . . ?
C3 C4 S1 111.13(10) . . ?
C8 C4 S1 126.26(10) . . ?
C6 C5 C3 120.37(13) . . ?
C6 C5 H5 119.8 . . ?
C3 C5 H5 119.8 . . ?
C5 C6 C7 121.50(13) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C9 C7 C6 121.49(12) 3_677 . ?
C9 C7 C8 118.85(12) 3_677 . ?
C6 C7 C8 119.66(12) . . ?
C9 C8 C4 124.05(12) . . ?
C9 C8 C7 119.35(12) . . ?
C4 C8 C7 116.60(12) . . ?
C8 C9 C7 121.81(12) . 3_677 ?
C8 C9 H9 119.1 . . ?
C7 C9 H9 119.1 3_677 . ?
C1 C10 C11 113.97(12) . . ?
C1 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C1 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 112.84(12) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 112.58(13) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 113.21(13) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 112.31(15) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 S1 C1 91.97(7) . . ?
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 1.349(2) . ?
C1 C10 1.4958(19) . ?
C1 S1 1.7342(14) . ?
C2 C3 1.4252(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3805(19) . ?
C3 C5 1.4204(19) . ?
C4 C8 1.4272(18) . ?
C4 S1 1.7227(13) . ?
C5 C6 1.349(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.4299(19) . ?
C6 H6 0.9500 . ?
C7 C9 1.3904(18) 3_677 ?
C7 C8 1.4302(18) . ?
C8 C9 1.3855(18) . ?
C9 C7 1.3904(18) 3_677 ?
C9 H9 0.9500 . ?
C10 C11 1.513(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5156(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.515(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.511(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.511(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
C10 C1 C2 C3 -178.73(14) . . . . ?
S1 C1 C2 C3 0.36(17) . . . . ?
C1 C2 C3 C4 -0.01(18) . . . . ?
C1 C2 C3 C5 178.02(15) . . . . ?
C5 C3 C4 C8 0.7(2) . . . . ?
C2 C3 C4 C8 178.91(13) . . . . ?
C5 C3 C4 S1 -178.59(11) . . . . ?
C2 C3 C4 S1 -0.36(15) . . . . ?
C4 C3 C5 C6 -0.1(2) . . . . ?
C2 C3 C5 C6 -178.02(15) . . . . ?
C3 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C9 -179.09(14) . . . 3_677 ?
C5 C6 C7 C8 1.2(2) . . . . ?
C3 C4 C8 C9 179.65(13) . . . . ?
S1 C4 C8 C9 -1.2(2) . . . . ?
C3 C4 C8 C7 -0.3(2) . . . . ?
S1 C4 C8 C7 178.85(11) . . . . ?
C9 C7 C8 C9 -0.3(2) 3_677 . . . ?
C6 C7 C8 C9 179.45(12) . . . . ?
C9 C7 C8 C4 179.66(13) 3_677 . . . ?
C6 C7 C8 C4 -0.60(19) . . . . ?
C4 C8 C9 C7 -179.64(13) . . . 3_677 ?
C7 C8 C9 C7 0.3(2) . . . 3_677 ?
C2 C1 C10 C11 140.04(16) . . . . ?
S1 C1 C10 C11 -38.99(18) . . . . ?
C1 C10 C11 C12 -173.68(13) . . . . ?
C10 C11 C12 C13 -174.11(13) . . . . ?
C11 C12 C13 C14 -176.56(13) . . . . ?
C12 C13 C14 C15 -177.95(14) . . . . ?
C3 C4 S1 C1 0.48(11) . . . . ?
C8 C4 S1 C1 -178.76(13) . . . . ?
C2 C1 S1 C4 -0.48(12) . . . . ?
C10 C1 S1 C4 178.70(12) . . . . ?
