#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:51:43 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179867 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/63/7016315.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_7016315
loop_
_publ_author_name
'Kato, Shinzi'
'Tani, Kazuyasu'
'Ishida, Masaru'
'Nonogaki, Junko'
'Ebihara, Masahiro'
'Hayashi, Satoko'
'Nakanishi, Waro'
'Niyomura, Osamu'
'Ando, Fumio'
'Koketsu, Jugo'
_publ_section_title
;
 Synthesis, structures and ab initio studies of selenium and tellurium
 bis(carbodithioates and carbothioates).
;
_journal_issue                   32
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8156
_journal_page_last               8169
_journal_paper_doi               10.1039/c1dt10208g
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C16 H14 O2 S4 Se'
_chemical_formula_sum            'C16 H14 O2 S4 Se'
_chemical_formula_weight         445.47
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 96.942(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.779(1)
_cell_length_b                   12.907(1)
_cell_length_c                   17.537(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10.0
_cell_volume                     1747.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_sigmaI/netI    0.0882
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4302
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0.46
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.631
_exptl_absorpt_correction_T_max  0.692
_exptl_absorpt_correction_T_min  0.540
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            reddish
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0377
_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)+(0.0216P)²+1.3750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                2512
_reflns_number_total             4013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10208g.txt
_cod_data_source_block           tani43
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               7016315
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_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
Se1 Se 0.19137(5) 0.53438(3) 0.43805(2) 0.02655(11) Uani 1 1 d .
S11 S 0.18145(16) 0.74961(8) 0.47806(6) 0.0379(3) Uani 1 1 d .
S12 S 0.02138(14) 0.62946(8) 0.34870(6) 0.0289(2) Uani 1 1 d .
C11 C 0.0471(5) 0.7451(3) 0.3972(2) 0.0221(8) Uani 1 1 d .
C12 C -0.0557(5) 0.8356(3) 0.3665(2) 0.0223(8) Uani 1 1 d .
C13 C -0.1169(5) 0.8502(3) 0.2878(2) 0.0213(8) Uani 1 1 d .
C14 C -0.2112(5) 0.9386(3) 0.2648(2) 0.0267(9) Uani 1 1 d .
H14 H -0.2505 0.9488 0.2119 0.032 Uiso 1 1 calc R
C15 C -0.2484(5) 1.0116(3) 0.3176(2) 0.0310(10) Uani 1 1 d .
H15 H -0.3158 1.0707 0.3012 0.037 Uiso 1 1 calc R
C16 C -0.1881(5) 0.9991(3) 0.3945(2) 0.0342(11) Uani 1 1 d .
H16 H -0.2121 1.0501 0.4308 0.041 Uiso 1 1 calc R
C17 C -0.0929(5) 0.9124(3) 0.4182(2) 0.0274(9) Uani 1 1 d .
H17 H -0.0515 0.9046 0.4711 0.033 Uiso 1 1 calc R
O11 O -0.0763(4) 0.7758(2) 0.23832(14) 0.0314(7) Uani 1 1 d .
C18 C -0.1412(6) 0.7878(3) 0.1591(2) 0.0317(10) Uani 1 1 d .
H18A H -0.2681 0.7881 0.1534 0.048 Uiso 1 1 calc R
H18B H -0.1006 0.7301 0.1296 0.048 Uiso 1 1 calc R
H18C H -0.0994 0.8533 0.1400 0.048 Uiso 1 1 calc R
S21 S 0.33191(16) 0.34783(9) 0.49697(6) 0.0378(3) Uani 1 1 d .
S22 S 0.12299(14) 0.40264(7) 0.35558(6) 0.0279(2) Uani 1 1 d .
C21 C 0.2322(5) 0.3096(3) 0.4128(2) 0.0223(8) Uani 1 1 d .
C22 C 0.2378(5) 0.2018(3) 0.3845(2) 0.0248(9) Uani 1 1 d .
C23 C 0.1639(5) 0.1696(3) 0.3106(2) 0.0254(9) Uani 1 1 d .
C24 C 0.1839(5) 0.0687(3) 0.2865(2) 0.0290(9) Uani 1 1 d .
H24 H 0.1361 0.0485 0.2362 0.035 Uiso 1 1 calc R
C25 C 0.2727(5) -0.0031(3) 0.3349(2) 0.0332(10) Uani 1 1 d .
H25 H 0.2854 -0.0723 0.3179 0.040 Uiso 1 1 calc R
C26 C 0.3433(6) 0.0262(3) 0.4082(2) 0.0345(10) Uani 1 1 d .
H26 H 0.4034 -0.0230 0.4417 0.041 Uiso 1 1 calc R
C27 C 0.3260(5) 0.1264(3) 0.4321(2) 0.0307(10) Uani 1 1 d .
H27 H 0.3753 0.1455 0.4823 0.037 Uiso 1 1 calc R
O21 O 0.0749(4) 0.2422(2) 0.26622(16) 0.0370(8) Uani 1 1 d .
C28 C 0.0030(5) 0.2162(3) 0.1895(2) 0.0324(10) Uani 1 1 d .
H28A H 0.0951 0.1910 0.1608 0.049 Uiso 1 1 calc R
H28B H -0.0507 0.2778 0.1641 0.049 Uiso 1 1 calc R
H28C H -0.0847 0.1620 0.1912 0.049 Uiso 1 1 calc R
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'
Se Se -0.0929 2.2259 '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
S22 Se1 S12 83.85(4)
C11 S12 Se1 95.98(13)
C12 C11 S11 122.7(3)
C12 C11 S12 118.7(3)
S11 C11 S12 118.5(2)
C17 C12 C13 117.8(3)
C17 C12 C11 117.9(3)
C13 C12 C11 124.2(3)
O11 C13 C14 123.4(3)
O11 C13 C12 116.9(3)
C14 C13 C12 119.7(3)
C15 C14 C13 120.9(4)
C15 C14 H14 119.6
C13 C14 H14 119.6
C14 C15 C16 120.2(4)
C14 C15 H15 119.9
C16 C15 H15 119.9
C17 C16 C15 119.7(4)
C17 C16 H16 120.2
C15 C16 H16 120.2
C16 C17 C12 121.7(4)
C16 C17 H17 119.1
C12 C17 H17 119.1
C13 O11 C18 117.6(3)
O11 C18 H18A 109.5
O11 C18 H18B 109.5
H18A C18 H18B 109.5
O11 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C21 S22 Se1 95.19(13)
C22 C21 S21 123.3(3)
C22 C21 S22 119.5(3)
S21 C21 S22 117.1(2)
C27 C22 C23 117.1(4)
C27 C22 C21 118.9(3)
C23 C22 C21 123.9(3)
O21 C23 C24 122.9(4)
O21 C23 C22 116.5(3)
C24 C23 C22 120.6(4)
C25 C24 C23 120.6(4)
C25 C24 H24 119.7
C23 C24 H24 119.7
C24 C25 C26 119.9(4)
C24 C25 H25 120.1
C26 C25 H25 120.1
C27 C26 C25 119.8(4)
C27 C26 H26 120.1
C25 C26 H26 120.1
C26 C27 C22 122.1(4)
C26 C27 H27 119.0
C22 C27 H27 119.0
C23 O21 C28 119.5(3)
O21 C28 H28A 109.5
O21 C28 H28B 109.5
H28A C28 H28B 109.5
O21 C28 H28C 109.5
H28A C28 H28C 109.5
H28B C28 H28C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 S22 2.2539(10)
Se1 S12 2.2824(10)
S11 C11 1.658(4)
S12 C11 1.717(4)
C11 C12 1.480(5)
C12 C17 1.397(5)
C12 C13 1.416(5)
C13 O11 1.357(4)
C13 C14 1.390(5)
C14 C15 1.376(5)
C14 H14 0.9500
C15 C16 1.382(5)
C15 H15 0.9500
C16 C17 1.379(5)
C16 H16 0.9500
C17 H17 0.9500
O11 C18 1.427(4)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
S21 C21 1.657(4)
S22 C21 1.722(4)
C21 C22 1.480(5)
C22 C27 1.405(5)
C22 C23 1.415(5)
C23 O21 1.355(4)
C23 C24 1.385(5)
C24 C25 1.384(5)
C24 H24 0.9500
C25 C26 1.388(5)
C25 H25 0.9500
C26 C27 1.371(5)
C26 H26 0.9500
C27 H27 0.9500
O21 C28 1.433(4)
C28 H28A 0.9800
C28 H28B 0.9800
C28 H28C 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
S22 Se1 S12 C11 -179.78(14)
Se1 S12 C11 C12 -173.6(3)
Se1 S12 C11 S11 4.3(3)
S11 C11 C12 C17 -24.7(5)
S12 C11 C12 C17 153.2(3)
S11 C11 C12 C13 154.4(3)
S12 C11 C12 C13 -27.7(5)
C17 C12 C13 O11 178.7(3)
C11 C12 C13 O11 -0.4(6)
C17 C12 C13 C14 -0.3(6)
C11 C12 C13 C14 -179.4(4)
O11 C13 C14 C15 -179.9(4)
C12 C13 C14 C15 -1.0(6)
C13 C14 C15 C16 1.8(6)
C14 C15 C16 C17 -1.1(6)
C15 C16 C17 C12 -0.3(7)
C13 C12 C17 C16 1.0(6)
C11 C12 C17 C16 -179.9(4)
C14 C13 O11 C18 -2.9(6)
C12 C13 O11 C18 178.2(3)
S12 Se1 S22 C21 -177.15(14)
Se1 S22 C21 C22 -177.5(3)
Se1 S22 C21 S21 0.6(2)
S21 C21 C22 C27 2.6(5)
S22 C21 C22 C27 -179.5(3)
S21 C21 C22 C23 -175.2(3)
S22 C21 C22 C23 2.7(5)
C27 C22 C23 O21 178.1(4)
C21 C22 C23 O21 -4.0(6)
C27 C22 C23 C24 -1.9(6)
C21 C22 C23 C24 175.9(4)
O21 C23 C24 C25 -178.5(4)
C22 C23 C24 C25 1.6(6)
C23 C24 C25 C26 -0.3(6)
C24 C25 C26 C27 -0.6(7)
C25 C26 C27 C22 0.2(7)
C23 C22 C27 C26 1.0(6)
C21 C22 C27 C26 -176.9(4)
C24 C23 O21 C28 -2.6(6)
C22 C23 O21 C28 177.4(4)
