#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/00/7150070.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_7150070
loop_
_publ_author_name
'Griffiths, Jon-Paul'
'Nie, Hui'
'Brown, R. James'
'Day, Peter'
'Wallis, John D.'
_publ_section_title
;
 Synthetic strategies to chiral organosulfur donors related to
 bis(ethylenedithio)tetrathiafulvalene.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2155
_journal_page_last               2166
_journal_paper_doi               10.1039/b502437d
_journal_volume                  3
_journal_year                    2005
_chemical_absolute_configuration syn
_chemical_formula_sum            'C13 H16 S5'
_chemical_formula_weight         332.56
_chemical_melting_point          412.5(5)
_chemical_name_common
;
(4aR,5R,7S,8aS)-4a,5,6,7,8,8a-Hexahydro-5,7-methano-4a,6,6-
trimethyl-1,3-dithiolo(4,5-b)-(1,4)benzodithiin-2-thione
;
_chemical_name_systematic
;
(4aR,5R,7S,8aS)-4a,5,6,7,8,8a-Hexahydro-5,7-methano-4a,6,6-trimethyl-
1,3-dithiolo[4,5-b]-[1,4]benzodithiin-2-thione
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.4053(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2322(2)
_cell_length_b                   9.3635(2)
_cell_length_c                   11.3961(3)
_cell_measurement_reflns_used    10374
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.94
_cell_volume                     740.31(3)
_computing_cell_refinement
;
'DENZO (Otwinowski and Minor, 1997)'
'COLLECT (Hooft, 1998)'
;
_computing_data_collection
;
'DENZO (Otwinowski and Minor, 1997)'
'COLLECT (Hooft, 1998)'
;
_computing_data_reduction
;
'DENZO (Otwinowski and Minor, 1997)'
'COLLECT (Hooft, 1998)'
;
_computing_molecular_graphics    'ORTEP3 (Johnson and Burnett, 1996)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10374
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Using multiple and symmetry-related data measurements via the program
SORTAV
See R. H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       shard
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0386
_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)+(0.0371P)²+0.2308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                3231
_reflns_number_total             3383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b502437d.txt
_cod_data_source_block           compound38
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '412-413' was changed to '412.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7150070
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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 0.50419(12) 0.93265(8) 0.16151(7) 0.02845(19) Uani 1 1 d . . .
S2 S 0.49223(10) 0.62083(7) 0.10891(6) 0.01990(16) Uani 1 1 d . . .
S3 S 0.18200(11) 0.74706(7) 0.18712(7) 0.02304(17) Uani 1 1 d . . .
S4 S 0.31017(10) 0.32467(7) 0.08413(6) 0.02040(16) Uani 1 1 d . . .
S5 S -0.04079(10) 0.46965(8) 0.16059(6) 0.02208(17) Uani 1 1 d . . .
C1 C 0.3974(4) 0.7754(3) 0.1523(3) 0.0220(6) Uani 1 1 d . . .
C2 C 0.3052(4) 0.5064(3) 0.1149(3) 0.0189(6) Uani 1 1 d . . .
C3 C 0.1599(4) 0.5650(3) 0.1511(2) 0.0197(6) Uani 1 1 d . . .
C4 C 0.2584(4) 0.2556(3) 0.2220(3) 0.0190(5) Uani 1 1 d . . .
C5 C 0.0603(4) 0.2984(3) 0.2390(3) 0.0191(6) Uani 1 1 d . . .
C6 C 0.0732(4) 0.3144(3) 0.3747(3) 0.0192(6) Uani 1 1 d . . .
C7 C 0.2012(4) 0.1952(3) 0.4576(3) 0.0208(6) Uani 1 1 d . . .
C8 C 0.3746(4) 0.2922(3) 0.4547(3) 0.0217(6) Uani 1 1 d . . .
C9 C 0.4332(4) 0.2744(3) 0.3368(3) 0.0214(6) Uani 1 1 d . . .
C10 C 0.2375(4) 0.4210(3) 0.4370(3) 0.0223(6) Uani 1 1 d . . .
C11 C -0.0963(4) 0.1919(4) 0.1748(3) 0.0253(6) Uani 1 1 d . . .
C12 C 0.2031(5) 0.0394(3) 0.4182(3) 0.0268(7) Uani 1 1 d . . .
C13 C 0.1617(5) 0.1944(4) 0.5832(3) 0.0292(7) Uani 1 1 d . . .
H11C H -0.089(5) 0.173(4) 0.085(3) 0.030(9) Uiso 1 1 d . . .
H11B H -0.230(5) 0.222(4) 0.176(3) 0.030(9) Uiso 1 1 d . . .
H11A H -0.085(5) 0.095(4) 0.217(3) 0.029(9) Uiso 1 1 d . . .
H4 H 0.242(5) 0.147(4) 0.189(3) 0.024(8) Uiso 1 1 d . . .
H9A H 0.506(4) 0.363(3) 0.327(3) 0.007(7) Uiso 1 1 d . . .
H9B H 0.510(5) 0.198(4) 0.344(3) 0.025(9) Uiso 1 1 d . . .
H8 H 0.493(5) 0.288(4) 0.527(3) 0.027(9) Uiso 1 1 d . . .
H6 H -0.055(5) 0.330(4) 0.389(3) 0.022(8) Uiso 1 1 d . . .
H10A H 0.264(4) 0.496(4) 0.390(3) 0.015(8) Uiso 1 1 d . . .
H10B H 0.226(5) 0.459(4) 0.516(3) 0.029(9) Uiso 1 1 d . . .
H13A H 0.024(5) 0.150(4) 0.580(3) 0.035(10) Uiso 1 1 d . . .
H13B H 0.162(5) 0.288(4) 0.614(3) 0.026(9) Uiso 1 1 d . . .
H13C H 0.252(5) 0.131(4) 0.643(3) 0.028(9) Uiso 1 1 d . . .
H12A H 0.235(5) 0.031(4) 0.339(3) 0.027(9) Uiso 1 1 d . . .
H12B H 0.078(6) -0.008(5) 0.411(4) 0.041(11) Uiso 1 1 d . . .
H12C H 0.306(6) -0.011(5) 0.479(4) 0.038(10) 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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S2 C2 97.37(14) . . ?
C1 S3 C3 97.11(14) . . ?
C2 S4 C4 98.72(13) . . ?
C3 S5 C5 104.41(13) . . ?
S1 C1 S2 123.19(18) . . ?
S1 C1 S3 123.78(18) . . ?
S2 C1 S3 113.03(18) . . ?
C3 C2 S4 121.4(2) . . ?
C3 C2 S2 116.3(2) . . ?
S4 C2 S2 122.21(16) . . ?
C2 C3 S5 123.2(2) . . ?
C2 C3 S3 116.1(2) . . ?
S5 C3 S3 120.64(16) . . ?
C9 C4 C5 115.3(2) . . ?
C9 C4 S4 111.6(2) . . ?
C5 C4 S4 115.8(2) . . ?
C6 C5 C11 111.9(2) . . ?
C6 C5 C4 110.9(2) . . ?
C11 C5 C4 110.9(2) . . ?
C6 C5 S5 107.56(19) . . ?
C11 C5 S5 101.1(2) . . ?
C4 C5 S5 114.2(2) . . ?
C5 C6 C10 110.1(2) . . ?
C5 C6 C7 113.2(2) . . ?
C10 C6 C7 86.4(2) . . ?
C12 C7 C13 106.8(3) . . ?
C12 C7 C8 118.5(3) . . ?
C13 C7 C8 112.7(2) . . ?
C12 C7 C6 123.4(2) . . ?
C13 C7 C6 109.2(3) . . ?
C8 C7 C6 85.1(2) . . ?
C9 C8 C10 107.4(2) . . ?
C9 C8 C7 112.4(2) . . ?
C10 C8 C7 88.1(2) . . ?
C8 C9 C4 113.1(2) . . ?
C8 C10 C6 86.4(2) . . ?
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 1.652(3) . ?
S2 C1 1.732(3) . ?
S2 C2 1.742(3) . ?
S3 C1 1.733(3) . ?
S3 C3 1.750(3) . ?
S4 C2 1.740(3) . ?
S4 C4 1.833(3) . ?
S5 C3 1.734(3) . ?
S5 C5 1.880(3) . ?
C2 C3 1.349(4) . ?
C4 C9 1.551(4) . ?
C4 C5 1.552(4) . ?
C5 C6 1.530(4) . ?
C5 C11 1.531(4) . ?
C6 C10 1.561(4) . ?
C6 C7 1.582(4) . ?
C7 C12 1.527(4) . ?
C7 C13 1.537(4) . ?
C7 C8 1.556(4) . ?
C8 C9 1.528(4) . ?
C8 C10 1.538(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9568335
