#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/22/8102273.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_8102273
loop_
_publ_author_name
'Fatemeh Darviche'
'Felora Heshmatpour'
'Zeynab Emdadi'
'Hamid Reza Khavasi'
'Bernhard Neumüller'
_publ_section_title
;
 Crystal structure of 5,6,7,8,9,10,11,12-octahydro[1,3]
 dithiolo[4,5-b][1,4] dithiacyclodecine-2-thione, C11H16S5
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              235
_journal_volume                  223
_journal_year                    2008
_chemical_formula_sum            'C11 H16 S5'
_chemical_formula_weight         308.59
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                   19.848(2)
_cell_length_b                   12.904(1)
_cell_length_c                   5.537(1)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      2.05
_cell_volume                     1418.1(3)
_computing_cell_refinement       'IPDS II (Stoe)'
_computing_data_collection       'IPDS II (Stoe)'
_computing_data_reduction        'IPDS II (Stoe)'
_computing_molecular_graphics    'SHELXTl-Plus (Sheldrick, 1990)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
 SIR-92 (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori,
        Camalli, 1992)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'IPDS II (Stoe)'
_diffrn_measurement_method       'IPDS II (Stoe)'
_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  0.1455
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            18620
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         25.93
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'small plates'
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.824
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0398
_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)+(0.0352P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                810
_reflns_number_total             1441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2249.cff
_cod_data_source_block           ga150
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               8102273
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.46672(4) 0.13880(6) 0.66746(17) 0.0463(3) Uani 1 1 d . . .
S2 S 0.56739(5) 0.12099(7) 1.07518(18) 0.0497(3) Uani 1 1 d . . .
S3 S 0.38095(7) 0.2500 0.3122(3) 0.0521(4) Uani 1 2 d S . .
C1 C 0.4360(2) 0.2500 0.5343(9) 0.0408(11) Uani 1 2 d S . .
C2 C 0.52217(15) 0.1981(2) 0.8719(6) 0.0385(8) Uani 1 1 d . . .
C3 C 0.60751(19) 0.0274(3) 0.8768(8) 0.0585(11) Uani 1 1 d . . .
H31 H 0.6355 -0.0195 0.9765 0.101(7) Uiso 1 1 calc R . .
H32 H 0.5719 -0.0151 0.8001 0.101(7) Uiso 1 1 calc R . .
C4 C 0.65036(18) 0.0718(3) 0.6845(7) 0.0613(11) Uani 1 1 d . . .
H41 H 0.6245 0.1167 0.5907 0.101(7) Uiso 1 1 d R . .
H42 H 0.6661 0.0192 0.5827 0.101(7) Uiso 1 1 d R . .
C51 C 0.70190(18) 0.1511(3) 0.7629(7) 0.066(3) Uani 0.50 1 d PR . 1
H511 H 0.7317 0.1113 0.8117 0.101(7) Uiso 0.50 1 d PR A 1
H512 H 0.6813 0.1946 0.8825 0.101(7) Uiso 0.50 1 d PR B 1
C52 C 0.7234(4) 0.2175(6) 0.5604(18) 0.061(3) Uani 0.50 1 d P . 1
H521 H 0.7443 0.1737 0.4422 0.101(7) Uiso 0.50 1 d PR . 1
H522 H 0.6850 0.2500 0.4902 0.101(7) Uiso 1 2 d SR . 1
C61 C 0.7237(4) 0.1088(8) 0.798(2) 0.084(4) Uani 0.50 1 d P . 2
H611 H 0.7427 0.0427 0.8079 0.101(7) Uiso 0.50 1 d PR . 2
H612 H 0.7082 0.1393 0.9227 0.101(7) Uiso 0.50 1 d PR . 2
C62 C 0.7584(4) 0.1806(7) 0.6101(17) 0.054(2) Uani 0.50 1 d P . 2
H621 H 0.8011 0.2027 0.6735 0.101(7) Uiso 0.50 1 d PR . 2
H622 H 0.7655 0.1428 0.4628 0.101(7) Uiso 0.50 1 d PR . 2
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
C1 S1 C2 97.72(17) . . ?
C2 S2 C3 102.36(17) . . ?
S3 C1 S1 123.66(14) . 8_565 ?
S3 C1 S1 123.66(14) . . ?
S1 C1 S1 112.6(3) 8_565 . ?
C2 C2 S2 124.66(10) 8_565 . ?
C2 C2 S1 115.87(10) 8_565 . ?
S2 C2 S1 119.24(16) . . ?
C4 C3 S2 115.5(3) . . ?
C4 C3 H31 108.4 . . ?
S2 C3 H31 108.4 . . ?
C4 C3 H32 108.4 . . ?
S2 C3 H32 108.4 . . ?
H31 C3 H32 107.5 . . ?
C3 C4 C51 116.4(2) . . ?
C3 C4 C61 110.2(6) . . ?
C51 C4 C61 25.9(4) . . ?
C3 C4 H41 109.0 . . ?
C51 C4 H41 96.4 . . ?
C61 C4 H41 121.1 . . ?
C3 C4 H42 110.2 . . ?
C51 C4 H42 116.0 . . ?
C61 C4 H42 98.2 . . ?
H41 C4 H42 107.4 . . ?
C52 C51 C4 111.8(4) . . ?
C52 C51 H511 113.6 . . ?
C4 C51 H511 99.0 . . ?
C52 C51 H512 108.0 . . ?
C4 C51 H512 107.8 . . ?
H511 C51 H512 116.3 . . ?
C52 C51 H612 143.2 . . ?
C4 C51 H612 105.0 . . ?
H511 C51 H612 58.6 . . ?
H512 C51 H612 58.9 . . ?
C52 C52 C51 125.5(3) 8_565 . ?
C52 C52 H521 126.1 8_565 . ?
C51 C52 H521 107.5 . . ?
C52 C52 H522 63.9 8_565 . ?
C51 C52 H522 109.5 . . ?
H521 C52 H522 109.1 . . ?
C52 C52 H622 134.1 8_565 . ?
C51 C52 H622 93.8 . . ?
H521 C52 H622 20.4 . . ?
H522 C52 H622 129.0 . . ?
C62 C61 C4 108.0(7) . . ?
C62 C61 H511 77.9 . . ?
C4 C61 H511 173.0 . . ?
C62 C61 H512 91.1 . . ?
C4 C61 H512 80.5 . . ?
H511 C61 H512 103.5 . . ?
C62 C61 H611 114.0 . . ?
C4 C61 H611 96.6 . . ?
H511 C61 H611 77.4 . . ?
H512 C61 H611 154.2 . . ?
C62 C61 H612 115.3 . . ?
C4 C61 H612 97.0 . . ?
H511 C61 H612 83.4 . . ?
H512 C61 H612 35.5 . . ?
H611 C61 H612 121.1 . . ?
C61 C62 C62 126.6(6) . 8_565 ?
C61 C62 H511 6.6 . . ?
C62 C62 H511 125.9 8_565 . ?
C61 C62 H521 117.1 . . ?
C62 C62 H521 95.2 8_565 . ?
H511 C62 H521 123.0 . . ?
C61 C62 H621 108.9 . . ?
C62 C62 H621 72.7 8_565 . ?
H511 C62 H621 102.3 . . ?
H521 C62 H621 129.0 . . ?
C61 C62 H622 109.3 . . ?
C62 C62 H622 120.5 8_565 . ?
H511 C62 H622 112.0 . . ?
H521 C62 H622 35.5 . . ?
H621 C62 H622 109.5 . . ?
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
S1 C1 1.724(3) . ?
S1 C2 1.755(3) . ?
S2 C2 1.750(3) . ?
S2 C3 1.816(4) . ?
S3 C1 1.645(5) . ?
C1 S1 1.724(3) 8_565 ?
C2 C2 1.339(6) 8_565 ?
C3 C4 1.478(5) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 C51 1.5111 . ?
C4 C61 1.655(11) . ?
C4 H41 0.9316 . ?
C4 H42 0.9357 . ?
C51 C52 1.474(10) . ?
C51 H511 0.8293 . ?
C51 H512 0.9600 . ?
C51 H612 0.9066 . ?
C52 C52 0.838(15) 8_565 ?
C52 H521 0.9600 . ?
C52 H522 0.9538 . ?
C61 C62 1.553(13) . ?
C61 H611 0.9337 . ?
C61 H612 0.8544 . ?
C62 H521 0.9751 . ?
C62 H621 0.9599 . ?
C62 H622 0.9600 . ?
