#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/36/1513692.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_1513692
loop_
_publ_author_name
'Young, Brian S'
'Chase, Daniel T'
'Marshall, Jonathan L'
'Vonnegut, Chris L'
'Zakharov, Lev N'
'Haley, Michael M'
_publ_section_title
;
 Synthesis and Properties of Fully-Conjugated Indacenedithiophenes.
;
_journal_issue                   3
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              1008
_journal_page_last               1014
_journal_paper_doi               10.1039/C3SC53181C
_journal_volume                  5
_journal_year                    2014
_chemical_formula_sum            'C34 H28 S2'
_chemical_formula_weight         500.68
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                91.725(4)
_cell_angle_beta                 107.227(4)
_cell_angle_gamma                105.087(4)
_cell_formula_units_Z            1
_cell_length_a                   7.9092(14)
_cell_length_b                   8.0857(14)
_cell_length_c                   10.8326(19)
_cell_measurement_reflns_used    5053
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.63
_cell_volume                     634.55(19)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'triumph mirror'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8463
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0604P)²+0.7934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                1893
_reflns_number_total             2237
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc53181c.txt
_cod_data_source_block           mo_mh114_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for
 ./tmp-cod-update-bibliographies-10052/cifs/1513692.cif.
;
_cod_original_cell_volume        634.54(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1513692
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.84680(8) 0.42922(8) 0.26869(6) 0.0208(2) Uani 1 1 d
C1 C 0.5018(3) -0.1496(3) 0.4253(2) 0.0132(5) Uani 1 1 d
C2 C 0.5847(3) 0.0197(3) 0.4029(2) 0.0135(5) Uani 1 1 d
C3 C 0.5813(3) 0.1686(3) 0.4802(2) 0.0127(5) Uani 1 1 d
C4 C 0.6780(3) 0.3204(3) 0.4330(2) 0.0154(5) Uani 1 1 d
C5 C 0.7349(3) 0.2613(3) 0.3352(2) 0.0153(5) Uani 1 1 d
C6 C 0.6778(3) 0.0749(3) 0.3136(2) 0.0141(5) Uani 1 1 d
C7 C 0.7257(3) 0.5038(3) 0.4537(2) 0.0124(5) Uani 1 1 d
C8 C 0.8174(4) 0.5762(3) 0.3721(3) 0.0231(6) Uani 1 1 d
C9 C 0.7064(3) -0.0356(3) 0.2149(2) 0.0140(5) Uani 1 1 d
C10 C 0.8864(3) -0.0335(3) 0.2180(2) 0.0160(5) Uani 1 1 d
C11 C 0.9085(3) -0.1386(3) 0.1232(2) 0.0179(5) Uani 1 1 d
C12 C 0.7611(3) -0.2465(3) 0.0275(2) 0.0194(5) Uani 1 1 d
C13 C 0.5844(3) -0.2490(3) 0.0266(2) 0.0167(5) Uani 1 1 d
C14 C 0.5544(3) -0.1443(3) 0.1176(2) 0.0149(5) Uani 1 1 d
C15 C 1.0538(4) 0.0714(4) 0.3245(3) 0.0216(6) Uani 1 1 d
C16 C 0.7903(5) -0.3590(4) -0.0734(3) 0.0308(7) Uani 1 1 d
C17 C 0.3597(3) -0.1477(3) 0.1060(2) 0.0176(5) Uani 1 1 d
H1 H 0.499(3) -0.245(3) 0.375(2) 0.017(6) Uiso 1 1 d
H7 H 0.701(3) 0.548(3) 0.500(2) 0.008(7) Uiso 1 1 d
H8 H 0.861(4) 0.687(4) 0.367(3) 0.030(8) Uiso 1 1 d
H11 H 1.025(4) -0.136(3) 0.127(2) 0.017(6) Uiso 1 1 d
H13 H 0.481(4) -0.324(3) -0.041(3) 0.017(6) Uiso 1 1 d
H15A H 1.040(5) 0.062(5) 0.403(4) 0.062(12) Uiso 1 1 d
H15B H 1.156(5) 0.045(4) 0.326(3) 0.051(10) Uiso 1 1 d
H15C H 1.067(5) 0.182(5) 0.324(3) 0.054(11) Uiso 1 1 d
H16A H 0.835(6) -0.449(6) -0.040(4) 0.077(13) Uiso 1 1 d
H16B H 0.880(5) -0.310(5) -0.096(4) 0.055(11) Uiso 1 1 d
H16C H 0.682(4) -0.392(4) -0.155(3) 0.037(8) Uiso 1 1 d
H17A H 0.288(4) -0.176(4) 0.020(3) 0.031(8) Uiso 1 1 d
H17B H 0.353(4) -0.037(4) 0.134(3) 0.026(7) Uiso 1 1 d
H17C H 0.308(4) -0.229(4) 0.156(3) 0.026(7) Uiso 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
C8 S1 C5 90.90(12) .
C3 C1 C2 118.3(2) 2_656
C3 C1 H1 120.4(16) 2_656
C2 C1 H1 121.2(16) .
C6 C2 C1 129.9(2) .
C6 C2 C3 109.7(2) .
C1 C2 C3 120.3(2) .
C1 C3 C2 121.4(2) 2_656
C1 C3 C4 132.5(2) 2_656
C2 C3 C4 106.13(18) .
C5 C4 C7 112.8(2) .
C5 C4 C3 107.0(2) .
C7 C4 C3 140.2(2) .
C4 C5 C6 111.2(2) .
C4 C5 S1 111.44(17) .
C6 C5 S1 137.32(18) .
C2 C6 C5 105.9(2) .
C2 C6 C9 126.7(2) .
C5 C6 C9 127.3(2) .
C8 C7 C4 111.0(2) .
C8 C7 H7 126(2) .
C4 C7 H7 123(2) .
C7 C8 S1 113.87(19) .
C7 C8 H8 127.4(19) .
S1 C8 H8 118.7(19) .
C14 C9 C10 119.5(2) .
C14 C9 C6 120.2(2) .
C10 C9 C6 120.3(2) .
C11 C10 C9 118.8(2) .
C11 C10 C15 119.2(2) .
C9 C10 C15 121.9(2) .
C12 C11 C10 122.5(2) .
C12 C11 H11 119.9(16) .
C10 C11 H11 117.6(16) .
C11 C12 C13 118.1(2) .
C11 C12 C16 121.0(2) .
C13 C12 C16 120.9(2) .
C12 C13 C14 121.8(2) .
C12 C13 H13 117.9(15) .
C14 C13 H13 120.2(15) .
C13 C14 C9 119.3(2) .
C13 C14 C17 118.6(2) .
C9 C14 C17 122.1(2) .
C10 C15 H15A 112(2) .
C10 C15 H15B 113(2) .
H15A C15 H15B 108(3) .
C10 C15 H15C 112(2) .
H15A C15 H15C 98(3) .
H15B C15 H15C 112(3) .
C12 C16 H16A 113(3) .
C12 C16 H16B 112(3) .
H16A C16 H16B 97(3) .
C12 C16 H16C 112.4(17) .
H16A C16 H16C 115(3) .
H16B C16 H16C 106(3) .
C14 C17 H17A 109.5(18) .
C14 C17 H17B 111.4(16) .
H17A C17 H17B 107(2) .
C14 C17 H17C 112.5(17) .
H17A C17 H17C 109(2) .
H17B C17 H17C 108(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C8 1.714(3) .
S1 C5 1.720(2) .
C1 C3 1.363(3) 2_656
C1 C2 1.418(3) .
C1 H1 0.93(3) .
C2 C6 1.398(3) .
C2 C3 1.456(3) .
C3 C1 1.363(3) 2_656
C3 C4 1.461(3) .
C4 C5 1.384(3) .
C4 C7 1.425(3) .
C5 C6 1.447(3) .
C6 C9 1.477(3) .
C7 C8 1.357(4) .
C7 H7 0.70(3) .
C8 H8 0.88(3) .
C9 C14 1.404(3) .
C9 C10 1.409(3) .
C10 C11 1.392(3) .
C10 C15 1.502(3) .
C11 C12 1.377(4) .
C11 H11 0.91(3) .
C12 C13 1.390(3) .
C12 C16 1.508(4) .
C13 C14 1.392(3) .
C13 H13 0.96(3) .
C14 C17 1.500(3) .
C15 H15A 0.89(4) .
C15 H15B 0.88(4) .
C15 H15C 0.87(4) .
C16 H16A 0.93(5) .
C16 H16B 0.82(4) .
C16 H16C 1.00(3) .
C17 H17A 0.92(3) .
C17 H17B 0.95(3) .
C17 H17C 0.95(3) .
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
C3 C1 C2 C6 179.9(2) 2_656 .
C3 C1 C2 C3 0.5(3) 2_656 .
C6 C2 C3 C1 180.0(2) . 2_656
C1 C2 C3 C1 -0.5(4) . 2_656
C6 C2 C3 C4 0.2(2) . .
C1 C2 C3 C4 179.75(19) . .
C1 C3 C4 C5 179.7(2) 2_656 .
C2 C3 C4 C5 -0.6(2) . .
C1 C3 C4 C7 -2.4(5) 2_656 .
C2 C3 C4 C7 177.3(3) . .
C7 C4 C5 C6 -177.75(19) . .
C3 C4 C5 C6 0.8(3) . .
C7 C4 C5 S1 0.0(3) . .
C3 C4 C5 S1 178.62(15) . .
C8 S1 C5 C4 0.24(18) . .
C8 S1 C5 C6 177.2(3) . .
C1 C2 C6 C5 -179.2(2) . .
C3 C2 C6 C5 0.3(2) . .
C1 C2 C6 C9 2.4(4) . .
C3 C2 C6 C9 -178.1(2) . .
C4 C5 C6 C2 -0.7(3) . .
S1 C5 C6 C2 -177.7(2) . .
C4 C5 C6 C9 177.6(2) . .
S1 C5 C6 C9 0.7(4) . .
C5 C4 C7 C8 -0.4(3) . .
C3 C4 C7 C8 -178.3(3) . .
C4 C7 C8 S1 0.6(3) . .
C5 S1 C8 C7 -0.5(2) . .
C2 C6 C9 C14 60.6(3) . .
C5 C6 C9 C14 -117.4(3) . .
C2 C6 C9 C10 -118.9(3) . .
C5 C6 C9 C10 63.0(3) . .
C14 C9 C10 C11 0.7(3) . .
C6 C9 C10 C11 -179.7(2) . .
C14 C9 C10 C15 -176.0(2) . .
C6 C9 C10 C15 3.5(3) . .
C9 C10 C11 C12 -1.0(3) . .
C15 C10 C11 C12 175.8(2) . .
C10 C11 C12 C13 0.1(3) . .
C10 C11 C12 C16 -179.7(2) . .
C11 C12 C13 C14 1.1(3) . .
C16 C12 C13 C14 -179.0(2) . .
C12 C13 C14 C9 -1.4(3) . .
C12 C13 C14 C17 176.8(2) . .
C10 C9 C14 C13 0.4(3) . .
C6 C9 C14 C13 -179.1(2) . .
C10 C9 C14 C17 -177.7(2) . .
C6 C9 C14 C17 2.7(3) . .
