#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/47/1504787.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_1504787
loop_
_publ_author_name
'Beer, Leanne'
'Reed, Robert W.'
'Robertson, Craig M.'
'Oakley, Richard T.'
'Tham, Fook S.'
'Haddon, Robert C.'
_publ_section_title
;
 Tetrathiophenalenyl radical and its disulfide-bridged dimer.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3121
_journal_page_last               3123
_journal_paper_doi               10.1021/ol801159z
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C26 H10 S8'
_chemical_formula_weight         578.82
_chemical_name_common            TTPLY
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.403(6)
_cell_length_b                   8.002(3)
_cell_length_c                   14.417(5)
_cell_measurement_reflns_used    317
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.98
_cell_measurement_theta_min      3.04
_cell_volume                     2123.1(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3524
_diffrn_reflns_av_sigmaI/netI    0.1732
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22155
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2171
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1828
_refine_ls_R_factor_gt           0.0609
_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)+(0.0446P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1425
_reflns_number_gt                980
_reflns_number_total             2171
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801159z-file006.cif
_cod_data_source_block           ttply_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2123.0(12)
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               1504787
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_refinement_flags
S1 S 0.39232(9) 0.1966(2) 0.52586(11) 0.0245(5) Uani 1 1 d .
C9 C 0.3776(3) 0.3840(9) 0.6920(4) 0.0179(15) Uani 1 1 d .
S4 S 0.02628(8) 0.3133(3) 0.68005(10) 0.0228(5) Uani 1 1 d .
C6A C 0.2516(4) 0.4883(8) 0.7823(4) 0.0181(15) Uani 1 1 d U
S3 S 0.09598(9) 0.2155(2) 0.51772(10) 0.0234(5) Uani 1 1 d .
C5 C 0.1195(4) 0.4927(9) 0.7919(4) 0.0215(16) Uani 1 1 d U
H5 H 0.0769 0.5281 0.8236 0.026 Uiso 1 1 calc R
S2 S 0.45210(9) 0.3105(3) 0.63014(11) 0.0256(5) Uani 1 1 d .
C8 C 0.3829(4) 0.4748(9) 0.7755(4) 0.0201(16) Uani 1 1 d U
H8 H 0.4290 0.4993 0.8019 0.024 Uiso 1 1 calc R
C3 C 0.1751(4) 0.2571(8) 0.5716(4) 0.0165(15) Uani 1 1 d U
C9B C 0.2445(4) 0.3948(8) 0.6983(4) 0.0146(13) Uani 1 1 d U
C4 C 0.1129(3) 0.3909(9) 0.7109(4) 0.0178(15) Uani 1 1 d U
C1 C 0.3074(4) 0.2502(8) 0.5705(4) 0.0204(17) Uani 1 1 d U
C7 C 0.3202(3) 0.5270(9) 0.8175(4) 0.0204(16) Uani 1 1 d U
H7 H 0.3235 0.5918 0.8726 0.024 Uiso 1 1 calc R
C2 C 0.2415(3) 0.2091(8) 0.5313(4) 0.0197(14) Uani 1 1 d U
H2 H 0.2409 0.1464 0.4754 0.024 Uiso 1 1 calc R
C6 C 0.1854(4) 0.5393(8) 0.8239(4) 0.0211(17) Uani 1 1 d .
H6 H 0.1875 0.6098 0.8768 0.025 Uiso 1 1 calc R
C9A C 0.3097(3) 0.3463(9) 0.6548(4) 0.0164(15) Uani 1 1 d U
C3A C 0.1760(3) 0.3484(9) 0.6614(4) 0.0172(15) Uani 1 1 d U
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_3
C1 S1 S2 95.7(2) .
C9A C9 C8 120.2(6) .
C9A C9 S2 115.9(5) .
C8 C9 S2 123.9(5) .
C4 S4 S4 99.4(2) 3_556
C7 C6A C6 124.0(6) .
C7 C6A C9B 120.4(7) .
C6 C6A C9B 115.5(6) .
C6 C5 C4 120.8(6) .
C6 C5 H5 119.6 .
C4 C5 H5 119.6 .
C9 S2 S1 95.9(2) .
C7 C8 C9 118.5(6) .
C7 C8 H8 120.8 .
C9 C8 H8 120.8 .
C2 C3 C3A 119.0(6) .
C2 C3 S3 120.4(5) .
C3A C3 S3 120.6(5) .
C9A C9B C3A 121.2(5) .
C9A C9B C6A 116.4(6) .
C3A C9B C6A 122.4(6) .
C3A C4 C5 118.9(6) .
C3A C4 S4 122.2(5) .
C5 C4 S4 118.8(5) .
C2 C1 C9A 120.0(6) .
C2 C1 S1 125.3(5) .
C9A C1 S1 114.7(5) .
C8 C7 C6A 122.3(7) .
C8 C7 H7 118.9 .
C6A C7 H7 118.9 .
C1 C2 C3 122.0(6) .
C1 C2 H2 119.0 .
C3 C2 H2 119.0 .
C5 C6 C6A 123.2(6) .
C5 C6 H6 118.4 .
C6A C6 H6 118.4 .
C9 C9A C9B 122.2(6) .
C9 C9A C1 117.9(6) .
C9B C9A C1 119.9(6) .
C4 C3A C9B 118.7(6) .
C4 C3A C3 123.5(6) .
C9B C3A C3 117.7(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.743(7) .
S1 S2 2.074(2) .
C9 C9A 1.393(8) .
C9 C8 1.409(9) .
C9 S2 1.739(7) .
S4 C4 1.768(7) .
S4 S4 2.237(3) 3_556
C6A C7 1.396(9) .
C6A C6 1.418(9) .
C6A C9B 1.430(8) .
S3 C3 1.684(6) .
C5 C6 1.350(9) .
C5 C4 1.429(9) .
C5 H5 0.9500 .
C8 C7 1.369(9) .
C8 H8 0.9500 .
C3 C2 1.407(9) .
C3 C3A 1.486(8) .
C9B C9A 1.408(8) .
C9B C3A 1.418(8) .
C4 C3A 1.404(8) .
C1 C2 1.377(9) .
C1 C9A 1.438(8) .
C7 H7 0.9500 .
C2 H2 0.9500 .
C6 H6 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
C9A C9 S2 S1 -0.1(5) .
C8 C9 S2 S1 179.1(6) .
C1 S1 S2 C9 -0.3(3) .
C9A C9 C8 C7 -1.2(10) .
S2 C9 C8 C7 179.6(5) .
C7 C6A C9B C9A -0.1(8) .
C6 C6A C9B C9A 178.6(6) .
C7 C6A C9B C3A 178.1(6) .
C6 C6A C9B C3A -3.2(9) .
C6 C5 C4 C3A -4.0(10) .
C6 C5 C4 S4 172.6(5) .
S4 S4 C4 C3A 150.8(5) 3_556
S4 S4 C4 C5 -25.7(6) 3_556
S2 S1 C1 C2 -180.0(6) .
S2 S1 C1 C9A 0.6(5) .
C9 C8 C7 C6A 2.3(10) .
C6 C6A C7 C8 179.8(7) .
C9B C6A C7 C8 -1.6(10) .
C9A C1 C2 C3 -0.5(10) .
S1 C1 C2 C3 -179.9(5) .
C3A C3 C2 C1 -2.8(9) .
S3 C3 C2 C1 175.9(5) .
C4 C5 C6 C6A -1.8(11) .
C7 C6A C6 C5 -176.0(7) .
C9B C6A C6 C5 5.3(9) .
C8 C9 C9A C9B -0.5(10) .
S2 C9 C9A C9B 178.7(5) .
C8 C9 C9A C1 -178.7(6) .
S2 C9 C9A C1 0.6(8) .
C3A C9B C9A C9 -177.1(6) .
C6A C9B C9A C9 1.2(9) .
C3A C9B C9A C1 1.0(9) .
C6A C9B C9A C1 179.3(6) .
C2 C1 C9A C9 179.7(6) .
S1 C1 C9A C9 -0.8(8) .
C2 C1 C9A C9B 1.5(9) .
S1 C1 C9A C9B -179.0(5) .
C5 C4 C3A C9B 5.9(9) .
S4 C4 C3A C9B -170.6(5) .
C5 C4 C3A C3 -174.0(6) .
S4 C4 C3A C3 9.5(9) .
C9A C9B C3A C4 175.9(6) .
C6A C9B C3A C4 -2.3(9) .
C9A C9B C3A C3 -4.2(9) .
C6A C9B C3A C3 177.6(6) .
C2 C3 C3A C4 -175.0(6) .
S3 C3 C3A C4 6.3(9) .
C2 C3 C3A C9B 5.1(9) .
S3 C3 C3A C9B -173.6(5) .
