#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/12/2221226.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_2221226
loop_
_publ_author_name
'Uludağ, Nesimi'
'Öztürk, Aslı'
'Hökelek, Tuncer'
'Erdoğan, Ümit Işık'
_publ_section_title
3,3-Ethylenedithio-3,3a,4,5,10,10b-hexahydro-2H-furo[2,3-a]carbazole
_journal_coeditor_code           XU2478
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o595
_journal_page_last               o596
_journal_paper_doi               10.1107/S1600536809006035
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H17 N O S2'
_chemical_formula_moiety         'C16 H17 N O S2'
_chemical_formula_sum            'C16 H17 N O S2'
_chemical_formula_weight         303.43
_chemical_name_systematic
;
3,3-Ethylenedithio-3,3a,4,5,10,10b-hexahydro-2H-
furo[2,3-a]carbazole
;
_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            8
_cell_length_a                   21.7617(5)
_cell_length_b                   8.4992(2)
_cell_length_c                   15.2115(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      16.7
_cell_measurement_theta_min      9.3
_cell_volume                     2813.47(11)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius TurboCAD-4'
_diffrn_measurement_method       'Non-profiled ω'
_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  0.1488
_diffrn_reflns_av_sigmaI/netI    0.1077
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8196
_diffrn_reflns_theta_full        24.30
_diffrn_reflns_theta_max         24.30
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.9435
_exptl_absorpt_correction_T_min  0.9125
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1458
_refine_ls_R_factor_gt           0.0412
_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)+(0.0328P)²+1.8766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                1105
_reflns_number_total             2289
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2478.cif
_cod_data_source_block           I
_cod_database_code               2221226
_cod_database_fobs_code          2221226
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.32178(5) 0.10773(14) 0.23756(8) 0.0538(4) Uani d . 1 . .
S S2 0.33505(5) -0.00621(14) 0.05706(9) 0.0538(3) Uani d . 1 . .
O O1 0.48005(12) 0.0372(3) 0.1141(2) 0.0597(9) Uani d . 1 . .
C C2 0.43301(17) -0.0004(5) 0.1754(3) 0.0499(12) Uani d . 1 . .
H H2A 0.4450 0.0310 0.2343 0.060 Uiso calc R 1 . .
H H2B 0.4250 -0.1126 0.1753 0.060 Uiso calc R 1 . .
C C3 0.37602(18) 0.0902(5) 0.1461(3) 0.0394(11) Uani d . 1 . .
C C3A 0.40456(17) 0.2447(4) 0.1109(3) 0.0391(11) Uani d . 1 . .
H H3A 0.3786 0.2865 0.0637 0.047 Uiso calc R 1 . .
C C4 0.41256(17) 0.3698(4) 0.1817(3) 0.0402(11) Uani d . 1 . .
H H4A 0.3724 0.4058 0.2008 0.048 Uiso calc R 1 . .
H H4B 0.4332 0.3238 0.2320 0.048 Uiso calc R 1 . .
C C5 0.44962(17) 0.5095(5) 0.1485(3) 0.0423(11) Uani d . 1 . .
H H5A 0.4272 0.5632 0.1023 0.051 Uiso calc R 1 . .
H H5B 0.4566 0.5834 0.1961 0.051 Uiso calc R 1 . .
C C5A 0.50957(18) 0.4512(4) 0.1140(3) 0.0375(10) Uani d . 1 . .
C C5B 0.56863(19) 0.5223(5) 0.1102(3) 0.0402(11) Uani d . 1 . .
C C6 0.5923(2) 0.6705(5) 0.1333(3) 0.0487(12) Uani d . 1 . .
H H6 0.5664 0.7483 0.1552 0.058 Uiso calc R 1 . .
C C7 0.6542(2) 0.6994(6) 0.1233(3) 0.0582(14) Uani d . 1 . .
H H7 0.6700 0.7973 0.1384 0.070 Uiso calc R 1 . .
C C8 0.6930(2) 0.5844(7) 0.0909(3) 0.0608(14) Uani d . 1 . .
H H8 0.7347 0.6070 0.0850 0.073 Uiso calc R 1 . .
C C9 0.6721(2) 0.4373(5) 0.0671(3) 0.0562(13) Uani d . 1 . .
H H9 0.6985 0.3607 0.0454 0.067 Uiso calc R 1 . .
C C9A 0.60977(19) 0.4090(5) 0.0771(3) 0.0426(11) Uani d . 1 . .
C C10A 0.51613(17) 0.3010(5) 0.0837(3) 0.0365(11) Uani d . 1 . .
C C10B 0.46569(17) 0.1854(4) 0.0715(3) 0.0401(11) Uani d . 1 . .
H H10B 0.4600 0.1667 0.0085 0.048 Uiso calc R 1 . .
N N10 0.57621(16) 0.2746(5) 0.0610(3) 0.0469(10) Uani d . 1 . .
H H10 0.5901(17) 0.196(4) 0.038(3) 0.043(15) Uiso d . 1 . .
C C11 0.2649(2) -0.0299(5) 0.1985(3) 0.0658(14) Uani d . 1 . .
H H11A 0.2507 -0.0947 0.2469 0.079 Uiso calc R 1 . .
H H11B 0.2299 0.0269 0.1750 0.079 Uiso calc R 1 . .
C C12 0.2921(2) -0.1318(5) 0.1286(3) 0.0646(14) Uani d . 1 . .
H H12A 0.2599 -0.1851 0.0961 0.078 Uiso calc R 1 . .
H H12B 0.3188 -0.2106 0.1545 0.078 Uiso calc R 1 . .
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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 S1 C3 . . 98.0(2) ?
C12 S2 C3 . . 94.1(2) ?
C2 O1 C10B . . 109.5(3) ?
O1 C2 C3 . . 106.3(3) ?
O1 C2 H2A . . 110.5 ?
O1 C2 H2B . . 110.5 ?
C3 C2 H2A . . 110.5 ?
C3 C2 H2B . . 110.5 ?
H2A C2 H2B . . 108.7 ?
S2 C3 S1 . . 106.7(2) ?
C2 C3 S1 . . 110.1(3) ?
C2 C3 S2 . . 112.9(3) ?
C2 C3 C3A . . 101.7(3) ?
C3A C3 S1 . . 116.9(3) ?
C3A C3 S2 . . 108.7(3) ?
C3 C3A H3A . . 109.3 ?
C4 C3A C3 . . 113.2(3) ?
C4 C3A H3A . . 109.3 ?
C4 C3A C10B . . 113.8(3) ?
C10B C3A C3 . . 101.7(3) ?
C10B C3A H3A . . 109.3 ?
C3A C4 H4A . . 109.3 ?
C3A C4 H4B . . 109.3 ?
C5 C4 C3A . . 111.8(3) ?
C5 C4 H4A . . 109.3 ?
C5 C4 H4B . . 109.3 ?
H4A C4 H4B . . 107.9 ?
C4 C5 H5A . . 109.9 ?
C4 C5 H5B . . 109.9 ?
C5A C5 C4 . . 108.7(3) ?
C5A C5 H5A . . 109.9 ?
C5A C5 H5B . . 109.9 ?
H5A C5 H5B . . 108.3 ?
C5B C5A C5 . . 131.6(4) ?
C10A C5A C5 . . 121.4(4) ?
C10A C5A C5B . . 106.8(4) ?
C6 C5B C5A . . 134.6(4) ?
C6 C5B C9A . . 118.0(4) ?
C9A C5B C5A . . 107.4(4) ?
C5B C6 H6 . . 120.3 ?
C7 C6 C5B . . 119.3(4) ?
C7 C6 H6 . . 120.3 ?
C6 C7 C8 . . 120.8(4) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C9 C8 C7 . . 122.1(4) ?
C9 C8 H8 . . 119.0 ?
C7 C8 H8 . . 119.0 ?
C8 C9 C9A . . 116.9(4) ?
C8 C9 H9 . . 121.5 ?
C9A C9 H9 . . 121.5 ?
C9 C9A C5B . . 122.9(4) ?
N10 C9A C9 . . 130.1(4) ?
N10 C9A C5B . . 107.1(4) ?
O1 C10B C3A . . 107.2(3) ?
O1 C10B C10A . . 111.1(3) ?
O1 C10B H10B . . 108.9 ?
N10 C10A C10B . . 124.4(4) ?
C3A C10B H10B . . 108.9 ?
C5A C10A N10 . . 109.8(4) ?
C5A C10A C10B . . 125.7(4) ?
C10A C10B C3A . . 111.9(3) ?
C10A C10B H10B . . 108.9 ?
C9A N10 H10 . . 124(3) ?
C10A N10 C9A . . 109.0(4) ?
C10A N10 H10 . . 127(3) ?
S1 C11 H11A . . 109.7 ?
S1 C11 H11B . . 109.7 ?
C12 C11 S1 . . 109.8(3) ?
C12 C11 H11A . . 109.7 ?
C12 C11 H11B . . 109.7 ?
H11A C11 H11B . . 108.2 ?
S2 C12 H12A . . 110.3 ?
S2 C12 H12B . . 110.3 ?
C11 C12 S2 . . 107.1(3) ?
C11 C12 H12A . . 110.3 ?
C11 C12 H12B . . 110.3 ?
H12A C12 H12B . . 108.6 ?
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
S1 C3 . 1.830(4) ?
S1 C11 . 1.803(4) ?
S2 C3 . 1.817(4) ?
S2 C12 . 1.788(4) ?
O1 C2 . 1.421(5) ?
O1 C10B . 1.450(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C2 . 1.526(5) ?
C3A C3 . 1.548(5) ?
C3A C4 . 1.523(5) ?
C3A C10B . 1.544(5) ?
C3A H3A . 0.9800 ?
C4 C5 . 1.522(5) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C5A C5 . 1.491(5) ?
C5A C10A . 1.365(5) ?
C5B C5A . 1.421(5) ?
C5B C6 . 1.405(5) ?
C6 H6 . 0.9300 ?
C7 C6 . 1.377(5) ?
C7 C8 . 1.383(6) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C8 . 1.379(6) ?
C9 H9 . 0.9300 ?
C9A C9 . 1.385(5) ?
C9A C5B . 1.408(5) ?
C10A C10B . 1.485(5) ?
C10B H10B . 0.9800 ?
N10 C10A . 1.371(5) ?
N10 C9A . 1.378(5) ?
N10 H10 . 0.81(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C11 . 1.495(6) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N10 H10 S2 5_655 0.81(4) 2.71(4) 3.487(4) 161(4) yes
C3A H3A Cg2 5_575 0.98 2.85 3.725(4) 149 yes
C4 H4B Cg1 4_555 0.97 2.79 3.556(5) 136 yes
C5 H5A Cg1 5_575 0.97 2.96 3.714(5) 135 yes
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 S1 C3 S2 . . . . 15.4(3) ?
C11 S1 C3 C2 . . . . -107.4(3) ?
C11 S1 C3 C3A . . . . 137.2(3) ?
C3 S1 C11 C12 . . . . 17.0(4) ?
C12 S2 C3 S1 . . . . -36.2(2) ?
C12 S2 C3 C2 . . . . 84.9(3) ?
C12 S2 C3 C3A . . . . -163.1(3) ?
C3 S2 C12 C11 . . . . 49.5(4) ?
C10B O1 C2 C3 . . . . 22.4(4) yes
C2 O1 C10B C3A . . . . 0.5(4) yes
C2 O1 C10B C10A . . . . 123.0(4) ?
C4 C3A C3 S1 . . . . 31.6(4) ?
C4 C3A C3 S2 . . . . 152.4(3) ?
C4 C3A C3 C2 . . . . -88.3(4) ?
C10B C3A C3 S1 . . . . 154.1(3) ?
C10B C3A C3 S2 . . . . -85.1(3) ?
C10B C3A C3 C2 . . . . 34.2(4) yes
C3 C3A C4 C5 . . . . 171.0(3) ?
C10B C3A C4 C5 . . . . 55.6(4) yes
C4 C3A C10B O1 . . . . 99.6(4) ?
C3 C3A C10B O1 . . . . -22.4(4) yes
C4 C3A C10B C10A . . . . -22.4(5) yes
C3 C3A C10B C10A . . . . -144.4(3) ?
S1 C3 C2 O1 . . . . -160.3(3) ?
S2 C3 C2 O1 . . . . 80.6(4) ?
C3A C3 C2 O1 . . . . -35.7(4) yes
C3A C4 C5 C5A . . . . -55.3(4) yes
C5B C5A C5 C4 . . . . -149.7(4) ?
C10A C5A C5 C4 . . . . 25.4(5) yes
C5A C5B C6 C7 . . . . 177.8(4) ?
C9A C5B C6 C7 . . . . -0.2(6) ?
C5 C5A C10A N10 . . . . -176.3(4) ?
C5 C5A C10A C10B . . . . 7.2(6) yes
C5B C5A C10A N10 . . . . -0.1(5) ?
C5B C5A C10A C10B . . . . -176.6(4) ?
C6 C5B C5A C5 . . . . -2.7(8) ?
C6 C5B C5A C10A . . . . -178.4(5) ?
C9A C5B C5A C5 . . . . 175.4(4) ?
C9A C5B C5A C10A . . . . -0.2(4) ?
C8 C7 C6 C5B . . . . -0.1(7) ?
C6 C7 C8 C9 . . . . 0.2(7) ?
C9A C9 C8 C7 . . . . 0.0(7) ?
N10 C9A C5B C5A . . . . 0.5(4) ?
N10 C9A C5B C6 . . . . 179.0(4) ?
C9 C9A C5B C5A . . . . -178.1(4) ?
C9 C9A C5B C6 . . . . 0.4(6) ?
N10 C9A C9 C8 . . . . -178.5(4) ?
C5B C9A C9 C8 . . . . -0.3(6) ?
N10 C10A C10B O1 . . . . 55.3(5) ?
N10 C10A C10B C3A . . . . 175.1(4) ?
C5A C10A C10B O1 . . . . -128.7(4) ?
C5A C10A C10B C3A . . . . -9.0(6) yes
C9A N10 C10A C5A . . . . 0.4(5) ?
C9A N10 C10A C10B . . . . 176.9(4) ?
C10A N10 C9A C5B . . . . -0.5(5) ?
C10A N10 C9A C9 . . . . 177.8(4) ?
S2 C12 C11 S1 . . . . -44.2(4) ?
