#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/43/2004364.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2004364
loop_
_publ_author_name
'Henderson, R. K.'
'MacNicol, D. D.'
'Rowan, S. J.'
_publ_section_title
;
 1,2-Bis[2,3,4,5,6-pentakis(phenylthio)phenyl]ethane
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              210
_journal_page_last               212
_journal_paper_doi               10.1107/S0108270195012716
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C74 H54 S10'
_chemical_formula_sum            'C74 H54 S10'
_chemical_formula_weight         1263.77
_chemical_name_systematic
;
1,2-Bis[penta(phenylthio)phenyl]ethane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.
_cell_angle_beta                 102.300(9)
_cell_angle_gamma                90.
_cell_formula_units_Z            2
_cell_length_a                   12.0031(10)
_cell_length_b                   19.527(3)
_cell_length_c                   13.953(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.06
_cell_measurement_theta_min      16.27
_cell_volume                     3195.3(7)
_computing_cell_refinement
'Enraf-Nonius SET4 (de Boer & Duisenberg, 1984)'
_computing_data_collection       'CAD-4 EXPRESS Software (Enraf-Nonius, 1992)'
_computing_data_reduction        'GX (Mallinson & Muir, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1971)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.1796
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6207
_diffrn_reflns_theta_max         25.52
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        15.4
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1316
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.998
_refine_ls_goodness_of_fit_obs   1.136
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_restrained_S_obs      1.136
_refine_ls_R_factor_all          0.2186
_refine_ls_R_factor_obs          0.0609
_refine_ls_shift/esd_max         -0.041
_refine_ls_shift/esd_mean        0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0631P)^2^ + 2.1159P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1877
_refine_ls_wR_factor_obs         0.1296
_reflns_number_observed          2408
_reflns_number_total             5955
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            cf1010.cif
_cod_data_source_block           cf1010
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2004364
loop_
_symmetry_equiv_pos_as_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_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
C7 1 0.0544(4) 0.0179(3) 0.9928(4) 0.0464(13) Uani d . C
H7A 1 0.0342(4) 0.0554(3) 0.9469(4) 0.070 Uiso calc R H
H7B 1 0.0944(4) 0.0369(3) 1.0549(4) 0.070 Uiso calc R H
C1 1 0.1326(4) -0.0313(2) 0.9544(4) 0.0423(13) Uani d . C
C2 1 0.1333(4) -0.0353(3) 0.8553(4) 0.0458(14) Uani d . C
C3 1 0.2016(4) -0.0850(3) 0.8202(4) 0.054(2) Uani d . C
C4 1 0.2645(4) -0.1315(3) 0.8850(5) 0.0514(15) Uani d . C
C5 1 0.2732(4) -0.1240(3) 0.9851(5) 0.054(2) Uani d . C
C6 1 0.2068(4) -0.0734(3) 1.0208(4) 0.0458(14) Uani d . C
S2 1 0.04782(13) 0.02197(8) 0.77202(11) 0.0577(4) Uani d . S
C12 1 -0.0470(5) -0.0346(3) 0.6947(4) 0.054(2) Uani d . C
C22 1 -0.0852(5) -0.0952(4) 0.7281(5) 0.067(2) Uani d . C
H22 1 -0.0622(5) -0.1077(4) 0.7936(5) 0.101 Uiso calc R H
C32 1 -0.1573(6) -0.1366(4) 0.6634(6) 0.081(2) Uani d . C
H32 1 -0.1825(6) -0.1775(4) 0.6856(6) 0.122 Uiso calc R H
C42 1 -0.1926(6) -0.1188(5) 0.5676(6) 0.089(2) Uani d . C
H42 1 -0.2399(6) -0.1479(5) 0.5243(6) 0.133 Uiso calc R H
C52 1 -0.1582(6) -0.0579(5) 0.5350(6) 0.089(2) Uani d . C
H52 1 -0.1843(6) -0.0449(5) 0.4700(6) 0.134 Uiso calc R H
C62 1 -0.0849(6) -0.0157(4) 0.5983(5) 0.074(2) Uani d . C
H62 1 -0.0611(6) 0.0255(4) 0.5758(5) 0.111 Uiso calc R H
S3 1 0.19438(13) -0.08933(10) 0.69216(12) 0.0738(6) Uani d . S
C13 1 0.3369(5) -0.0800(3) 0.6791(5) 0.062(2) Uani d . C
C23 1 0.4263(6) -0.0598(4) 0.7534(6) 0.085(2) Uani d . C
H23 1 0.4153(6) -0.0525(4) 0.8166(6) 0.127 Uiso calc R H
C33 1 0.5323(7) -0.0507(4) 0.7319(9) 0.116(3) Uani d . C
H33 1 0.5933(7) -0.0380(4) 0.7819(9) 0.174 Uiso calc R H
C43 1 0.5499(10) -0.0595(5) 0.6411(11) 0.137(5) Uani d . C
H43 1 0.6219(10) -0.0527(5) 0.6281(11) 0.205 Uiso calc R H
C53 1 0.4603(11) -0.0788(5) 0.5672(9) 0.136(4) Uani d . C
H53 1 0.4718(11) -0.0846(5) 0.5039(9) 0.204 Uiso calc R H
C63 1 0.3538(7) -0.0898(4) 0.5861(6) 0.093(2) Uani d . C
H63 1 0.2938(7) -0.1036(4) 0.5361(6) 0.139 Uiso calc R H
S4 1 0.32938(14) -0.20278(9) 0.83924(15) 0.0754(6) Uani d . S
C14 1 0.2228(5) -0.2661(3) 0.8335(4) 0.057(2) Uani d . C
C24 1 0.1136(6) -0.2535(4) 0.8462(5) 0.078(2) Uani d . C
H24 1 0.0925(6) -0.2097(4) 0.8614(5) 0.116 Uiso calc R H
C34 1 0.0365(7) -0.3064(4) 0.8363(5) 0.093(2) Uani d . C
H34 1 -0.0368(7) -0.2985(4) 0.8457(5) 0.140 Uiso calc R H
C44 1 0.0675(9) -0.3716(4) 0.8125(6) 0.097(3) Uani d . C
H44 1 0.0150(9) -0.4072(4) 0.8057(6) 0.145 Uiso calc R H
C54 1 0.1767(9) -0.3836(4) 0.7989(5) 0.092(2) Uani d . C
H54 1 0.1978(9) -0.4271(4) 0.7823(5) 0.138 Uiso calc R H
C64 1 0.2532(6) -0.3308(3) 0.8101(5) 0.072(2) Uani d . C
H64 1 0.3269(6) -0.3388(3) 0.8017(5) 0.107 Uiso calc R H
S5 1 0.35817(14) -0.17971(9) 1.07201(14) 0.0776(6) Uani d . S
C15 1 0.4984(5) -0.1671(3) 1.0518(4) 0.056(2) Uani d . C
C25 1 0.5729(5) -0.2220(3) 1.0753(4) 0.061(2) Uani d . C
H25 1 0.5467(5) -0.2637(3) 1.0938(4) 0.092 Uiso calc R H
C35 1 0.6848(5) -0.2142(4) 1.0712(5) 0.077(2) Uani d . C
H35 1 0.7355(5) -0.2503(4) 1.0888(5) 0.115 Uiso calc R H
C45 1 0.7221(6) -0.1538(5) 1.0415(6) 0.096(3) Uani d . C
H45 1 0.7985(6) -0.1489(5) 1.0390(6) 0.145 Uiso calc R H
C55 1 0.6476(7) -0.0992(5) 1.0146(6) 0.112(3) Uani d . C
H55 1 0.6733(7) -0.0588(5) 0.9915(6) 0.168 Uiso calc R H
C65 1 0.5345(6) -0.1053(4) 1.0224(5) 0.084(2) Uani d . C
H65 1 0.4846(6) -0.0685(4) 1.0081(5) 0.126 Uiso calc R H
S6 1 0.22035(14) -0.06069(8) 1.14825(12) 0.0636(5) Uani d . S
C16 1 0.1709(5) -0.1367(4) 1.1922(5) 0.067(2) Uani d . C
C26 1 0.1036(6) -0.1836(4) 1.1351(7) 0.091(2) Uani d . C
H26 1 0.0815(6) -0.1774(4) 1.0676(7) 0.137 Uiso calc R H
C36 1 0.0683(8) -0.2414(5) 1.1798(9) 0.128(4) Uani d . C
H36 1 0.0235(8) -0.2742(5) 1.1413(9) 0.192 Uiso calc R H
C46 1 0.0987(11) -0.2505(6) 1.2792(13) 0.148(6) Uani d . C
H46 1 0.0745(11) -0.2888(6) 1.3086(13) 0.222 Uiso calc R H
C56 1 0.1651(11) -0.2021(7) 1.3342(9) 0.157(5) Uani d . C
H56 1 0.1860(11) -0.2081(7) 1.4018(9) 0.236 Uiso calc R H
C66 1 0.2021(7) -0.1453(5) 1.2937(6) 0.107(3) Uani d . C
H66 1 0.2473(7) -0.1130(5) 1.3328(6) 0.161 Uiso calc R H
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 1 7
-6 -1 0
-2 15 -1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 C7 C7 3_557 111.5(5) y
C2 C1 C6 . 119.1(5) y
C2 C1 C7 . 121.5(5) y
C6 C1 C7 . 119.3(5) y
C1 C2 C3 . 120.5(5) y
C1 C2 S2 . 119.5(4) y
C3 C2 S2 . 119.9(4) y
C4 C3 C2 . 119.7(5) y
C4 C3 S3 . 122.0(5) y
C2 C3 S3 . 118.2(4) y
C3 C4 C5 . 120.2(5) y
C3 C4 S4 . 119.9(5) y
C5 C4 S4 . 119.9(5) y
C4 C5 C6 . 119.8(5) y
C4 C5 S5 . 122.1(5) y
C6 C5 S5 . 117.9(5) y
C1 C6 C5 . 119.9(5) y
C1 C6 S6 . 119.4(4) y
C5 C6 S6 . 120.7(4) y
C2 S2 C12 . 102.2(3) y
C62 C12 C22 . 119.6(6) ?
C62 C12 S2 . 117.5(5) y
C22 C12 S2 . 122.8(5) y
C32 C22 C12 . 119.3(7) ?
C42 C32 C22 . 121.1(8) ?
C32 C42 C52 . 119.8(8) ?
C42 C52 C62 . 120.2(8) ?
C12 C62 C52 . 119.9(7) ?
C13 S3 C3 . 105.0(3) y
C63 C13 C23 . 120.2(7) ?
C63 C13 S3 . 115.2(6) y
C23 C13 S3 . 124.5(5) y
C13 C23 C33 . 118.6(8) ?
C43 C33 C23 . 121.8(10) ?
C33 C43 C53 . 119.3(10) ?
C43 C53 C63 . 120.7(10) ?
C13 C63 C53 . 119.4(9) ?
C14 S4 C4 . 101.3(3) y
C64 C14 C24 . 120.1(6) ?
C64 C14 S4 . 115.3(5) y
C24 C14 S4 . 124.5(5) y
C34 C24 C14 . 119.3(7) ?
C24 C34 C44 . 120.4(8) ?
C54 C44 C34 . 119.9(7) ?
C64 C54 C44 . 119.3(7) ?
C54 C64 C14 . 121.0(7) ?
C5 S5 C15 . 103.4(3) y
C65 C15 C25 . 121.3(6) ?
C65 C15 S5 . 122.5(5) y
C25 C15 S5 . 116.0(5) y
C35 C25 C15 . 119.6(6) ?
C45 C35 C25 . 120.1(7) ?
C35 C45 C55 . 120.9(7) ?
C65 C55 C45 . 119.7(7) ?
C15 C65 C55 . 118.3(7) ?
C16 S6 C6 . 105.5(3) y
C26 C16 C66 . 120.7(7) ?
C26 C16 S6 . 124.5(6) y
C66 C16 S6 . 114.8(7) y
C16 C26 C36 . 118.7(9) ?
C46 C36 C26 . 121.0(11) ?
C56 C46 C36 . 118.6(11) ?
C66 C56 C46 . 122.3(12) ?
C56 C66 C16 . 118.6(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C7 C1 . 1.519(7) y
C7 C7 3_557 1.532(9) y
C1 C2 . 1.387(7) y
C1 C6 . 1.405(7) y
C2 C3 . 1.423(7) y
C2 S2 . 1.773(6) y
C3 C4 . 1.386(8) y
C3 S3 . 1.772(6) y
C4 C5 . 1.386(7) y
C4 S4 . 1.779(6) y
C5 C6 . 1.425(8) y
C5 S5 . 1.780(6) y
C6 S6 . 1.768(6) y
S2 C12 . 1.777(6) y
C12 C62 . 1.376(8) ?
C12 C22 . 1.384(8) ?
C22 C32 . 1.373(8) ?
C32 C42 . 1.359(9) ?
C42 C52 . 1.368(10) ?
C52 C62 . 1.378(9) ?
S3 C13 . 1.768(6) y
C13 C63 . 1.369(9) ?
C13 C23 . 1.381(9) ?
C23 C33 . 1.379(10) ?
C33 C43 . 1.340(14) ?
C43 C53 . 1.374(14) ?
C53 C63 . 1.375(11) ?
S4 C14 . 1.769(6) y
C14 C64 . 1.373(8) ?
C14 C24 . 1.382(8) ?
C24 C34 . 1.374(9) ?
C34 C44 . 1.386(11) ?
C44 C54 . 1.384(11) ?
C54 C64 . 1.367(9) ?
S5 C15 . 1.782(6) y
C15 C65 . 1.375(8) ?
C15 C25 . 1.389(8) ?
C25 C35 . 1.364(8) ?
C35 C45 . 1.357(10) ?
C45 C55 . 1.391(11) ?
C55 C65 . 1.389(10) ?
S6 C16 . 1.757(7) y
C16 C26 . 1.361(9) ?
C16 C66 . 1.395(9) ?
C26 C36 . 1.398(11) ?
C36 C46 . 1.368(15) ?
C46 C56 . 1.36(2) ?
C56 C66 . 1.361(13) ?
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_site_symmetry_1
_geom_torsion
_geom_torsion_publ_flag
C7 C7 C1 C2 3_557 97.2(7) ?
C7 C7 C1 C6 3_557 -83.3(7) y
C6 C1 C2 C3 . 4.8(7) ?
C7 C1 C2 C3 . -175.7(4) ?
C6 C1 C2 S2 . -175.4(4) ?
C7 C1 C2 S2 . 4.1(7) y
C1 C2 C3 C4 . 2.5(8) ?
S2 C2 C3 C4 . -177.3(4) ?
C1 C2 C3 S3 . 177.7(4) ?
S2 C2 C3 S3 . -2.1(6) ?
C2 C3 C4 C5 . -8.7(8) ?
S3 C3 C4 C5 . 176.3(4) ?
C2 C3 C4 S4 . 168.8(4) ?
S3 C3 C4 S4 . -6.2(6) ?
C3 C4 C5 C6 . 7.4(8) ?
S4 C4 C5 C6 . -170.1(4) ?
C3 C4 C5 S5 . -177.0(4) ?
S4 C4 C5 S5 . 5.5(7) ?
C2 C1 C6 C5 . -6.1(7) ?
C7 C1 C6 C5 . 174.4(5) ?
C2 C1 C6 S6 . 171.6(4) ?
C7 C1 C6 S6 . -7.9(6) y
C4 C5 C6 C1 . 0.1(8) ?
S5 C5 C6 C1 . -175.8(4) ?
C4 C5 C6 S6 . -177.6(4) ?
S5 C5 C6 S6 . 6.5(6) ?
C1 C2 S2 C12 . -117.9(4) ?
C3 C2 S2 C12 . 62.0(5) y
C2 S2 C12 C62 . -148.2(5) ?
C2 S2 C12 C22 . 33.2(5) y
C62 C12 C22 C32 . 2.3(9) ?
S2 C12 C22 C32 . -179.2(5) ?
C12 C22 C32 C42 . -0.6(10) ?
C22 C32 C42 C52 . -1.6(11) ?
C32 C42 C52 C62 . 2.2(12) ?
C22 C12 C62 C52 . -1.7(9) ?
S2 C12 C62 C52 . 179.7(5) ?
C42 C52 C62 C12 . -0.6(11) ?
C4 C3 S3 C13 . -60.2(5) y
C2 C3 S3 C13 . 124.7(4) ?
C3 S3 C13 C63 . 172.8(5) ?
C3 S3 C13 C23 . -11.7(6) y
C63 C13 C23 C33 . -0.9(10) ?
S3 C13 C23 C33 . -176.2(6) ?
C13 C23 C33 C43 . 1.4(13) ?
C23 C33 C43 C53 . -0.6(16) ?
C33 C43 C53 C63 . -0.7(17) ?
C23 C13 C63 C53 . -0.3(11) ?
S3 C13 C63 C53 . 175.4(7) ?
C43 C53 C63 C13 . 1.2(15) ?
C3 C4 S4 C14 . -92.9(5) ?
C5 C4 S4 C14 . 84.6(5) y
C4 S4 C14 C64 . -173.2(5) ?
C4 S4 C14 C24 . 9.8(6) y
C64 C14 C24 C34 . 0.7(10) ?
S4 C14 C24 C34 . 177.5(5) ?
C14 C24 C34 C44 . -0.9(11) ?
C24 C34 C44 C54 . 0.2(12) ?
C34 C44 C54 C64 . 0.6(12) ?
C44 C54 C64 C14 . -0.8(11) ?
C24 C14 C64 C54 . 0.1(10) ?
S4 C14 C64 C54 . -177.0(5) ?
C4 C5 S5 C15 . 61.2(5) y
C6 C5 S5 C15 . -123.0(4) ?
C5 S5 C15 C65 . 32.4(7) y
C5 S5 C15 C25 . -152.8(5) ?
C65 C15 C25 C35 . 1.3(10) ?
S5 C15 C25 C35 . -173.6(5) ?
C15 C25 C35 C45 . -2.0(10) ?
C25 C35 C45 C55 . -0.2(12) ?
C35 C45 C55 C65 . 2.9(13) ?
C25 C15 C65 C55 . 1.4(11) ?
S5 C15 C65 C55 . 176.0(6) ?
C45 C55 C65 C15 . -3.5(12) ?
C1 C6 S6 C16 . 116.9(4) ?
C5 C6 S6 C16 . -65.4(5) y
C6 S6 C16 C26 . -19.0(6) y
C6 S6 C16 C66 . 163.4(5) ?
C66 C16 C26 C36 . -1.3(10) ?
S6 C16 C26 C36 . -178.8(5) ?
C16 C26 C36 C46 . 1.2(13) ?
C26 C36 C46 C56 . -0.5(17) ?
C36 C46 C56 C66 . 0.0(19) ?
C46 C56 C66 C16 . -0.1(16) ?
C26 C16 C66 C56 . 0.8(12) ?
S6 C16 C66 C56 . 178.5(7) ?
