#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202531.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_2202531
loop_
_publ_author_name
'Sundar, T. V.'
'Parthasarathi, V.'
'Garc\'ia-Granda, S.'
'Jain, Abhinandan'
'Pardasani, R. T.'
_publ_section_title
;
 2-(3-Ethyl-2,3,4,5-tetrahydro-4-oxo-2-thioxo-4-thiazolidin-5-ylidene)-1,2-dihydroacenaphthylen-1-one
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1967
_journal_page_last               o1969
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C17 H11 N O2 S2'
_chemical_formula_moiety         'C17 H11 N O2 S2'
_chemical_formula_sum            'C17 H11 N O2 S2'
_chemical_formula_weight         325.39
_chemical_melting_point          483
_chemical_name_systematic
;
2-(3-Ethyl-2,3,4,5-tetrahydro-4-oxo-2-thioxo-4-thiazolidin-5-ylidene)-
1,2-dihydroacenaphthylen-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.911(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.382(5)
_cell_length_b                   26.375(5)
_cell_length_c                   7.511(5)
_cell_measurement_reflns_used    2248
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.0
_cell_measurement_theta_min      2.0
_cell_volume                     1460.5(14)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997--2000)'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_molecular_graphics    'WINGX (Farrugia, 1999)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF99 (Beurskens et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.860
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f scans with \k offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4416
_diffrn_reflns_theta_full        69.19
_diffrn_reflns_theta_max         69.19
_diffrn_reflns_theta_min         3.35
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.357
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0517
_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/[\s^2^(Fo^2^)+(0.0792P)^2^+0.1394P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1512
_reflns_number_gt                1427
_reflns_number_total             2338
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ci6302.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '483 K' was changed to '483' - the
value should be numeric and without a unit
designator.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2202531
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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_type_symbol
S1 0.24945(12) 0.36221(4) 0.16933(13) 0.0567(3) Uani d . 1 S
S2 0.31324(16) 0.47252(4) 0.19844(17) 0.0803(4) Uani d . 1 S
C9 0.5131(4) 0.22481(12) 0.2912(5) 0.0482(9) Uani d . 1 C
O2 0.7115(3) 0.32990(10) 0.3940(4) 0.0705(8) Uani d . 1 O
O1 0.0956(3) 0.27197(10) 0.0949(4) 0.0719(8) Uani d . 1 O
C1 0.2213(5) 0.24661(13) 0.1580(5) 0.0501(9) Uani d . 1 C
N1 0.5417(4) 0.39931(11) 0.3175(4) 0.0578(8) Uani d . 1 N
C11 0.4093(4) 0.18059(13) 0.2474(5) 0.0475(9) Uani d . 1 C
C14 0.5741(5) 0.34747(14) 0.3285(5) 0.0526(9) Uani d . 1 C
C13 0.4153(4) 0.31942(12) 0.2469(5) 0.0485(9) Uani d . 1 C
C2 0.2360(4) 0.19139(13) 0.1697(4) 0.0496(9) Uani d . 1 C
C3 0.1202(5) 0.15282(14) 0.1220(5) 0.0593(10) Uani d . 1 C
H3 0.0058 0.1594 0.0695 0.071 Uiso calc R 1 H
C12 0.3961(4) 0.26867(13) 0.2382(5) 0.0484(9) Uani d . 1 C
C8 0.6845(5) 0.21850(14) 0.3658(5) 0.0560(10) Uani d . 1 C
H8 0.7577 0.2464 0.3938 0.067 Uiso calc R 1 H
C10 0.4711(5) 0.13139(13) 0.2767(5) 0.0534(9) Uani d . 1 C
C15 0.3819(5) 0.41470(13) 0.2348(5) 0.0562(10) Uani d . 1 C
C6 0.6470(5) 0.12590(14) 0.3556(5) 0.0600(10) Uani d . 1 C
H6 0.6947 0.0938 0.3781 0.072 Uiso calc R 1 H
C4 0.1794(5) 0.10254(15) 0.1546(5) 0.0664(11) Uani d . 1 C
H4 0.1008 0.0759 0.1256 0.080 Uiso calc R 1 H
C5 0.3477(5) 0.09190(14) 0.2272(5) 0.0617(11) Uani d . 1 C
H5 0.3825 0.0583 0.2447 0.074 Uiso calc R 1 H
C7 0.7480(5) 0.16844(14) 0.3996(5) 0.0608(11) Uani d . 1 C
H7 0.8631 0.1642 0.4538 0.073 Uiso calc R 1 H
C16 0.6765(5) 0.43519(15) 0.3980(6) 0.0682(11) Uani d . 1 C
H16A 0.7362 0.4199 0.5027 0.082 Uiso calc R 1 H
H16B 0.6152 0.4656 0.4353 0.082 Uiso calc R 1 H
C17 0.8163(6) 0.44903(17) 0.2669(6) 0.0860(14) Uani d . 1 C
H17A 0.8818 0.4192 0.2353 0.129 Uiso calc R 1 H
H17B 0.8991 0.4734 0.3201 0.129 Uiso calc R 1 H
H17C 0.7569 0.4633 0.1618 0.129 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0507(5) 0.0554(6) 0.0633(7) 0.0027(4) -0.0032(5) 0.0048(4)
S2 0.0796(7) 0.0547(7) 0.1057(11) 0.0064(5) -0.0043(7) 0.0071(6)
C9 0.0444(18) 0.056(2) 0.044(2) -0.0009(16) -0.0018(17) -0.0010(17)
O2 0.0597(16) 0.0598(17) 0.089(2) 0.0015(13) -0.0251(16) 0.0002(15)
O1 0.0545(15) 0.0635(17) 0.095(2) 0.0026(13) -0.0194(15) 0.0051(15)
C1 0.050(2) 0.055(2) 0.045(3) -0.0004(17) -0.0041(18) 0.0018(17)
N1 0.0527(17) 0.0535(19) 0.066(2) -0.0021(14) -0.0044(17) -0.0022(15)
C11 0.0469(18) 0.052(2) 0.043(2) -0.0026(16) 0.0006(18) -0.0044(17)
C14 0.052(2) 0.056(2) 0.049(3) -0.0013(17) -0.0059(19) -0.0011(17)
C13 0.0474(18) 0.050(2) 0.048(2) -0.0020(15) -0.0002(18) -0.0005(17)
C2 0.0466(19) 0.056(2) 0.045(3) -0.0012(16) -0.0021(18) 0.0026(16)
C3 0.051(2) 0.063(3) 0.062(3) -0.0055(18) -0.0086(19) -0.0040(19)
C12 0.0441(18) 0.054(2) 0.046(2) 0.0028(16) -0.0010(17) 0.0043(17)
C8 0.050(2) 0.057(2) 0.060(3) 0.0004(17) -0.0039(19) -0.0019(18)
C10 0.060(2) 0.053(2) 0.047(3) 0.0012(17) 0.000(2) -0.0039(17)
C15 0.054(2) 0.056(2) 0.059(3) 0.0013(17) 0.002(2) 0.0005(18)
C6 0.059(2) 0.056(2) 0.064(3) 0.0070(18) -0.006(2) -0.0015(19)
C4 0.066(2) 0.061(3) 0.071(3) -0.013(2) -0.003(2) -0.010(2)
C5 0.068(2) 0.050(2) 0.067(3) -0.0017(18) 0.003(2) -0.0047(19)
C7 0.052(2) 0.061(3) 0.068(3) 0.0071(18) -0.008(2) -0.001(2)
C16 0.067(2) 0.060(2) 0.076(3) -0.005(2) -0.012(2) -0.006(2)
C17 0.073(3) 0.081(3) 0.105(4) -0.008(2) 0.010(3) -0.001(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_publ_flag
C13 S1 C15 92.61(18) ?
C8 C9 C11 118.1(3) ?
C8 C9 C12 135.9(3) ?
C11 C9 C12 106.1(3) ?
O1 C1 C2 128.5(3) ?
O1 C1 C12 124.1(3) ?
C2 C1 C12 107.5(3) ?
C15 N1 C14 117.4(3) yes
C15 N1 C16 122.9(3) yes
C14 N1 C16 119.7(3) yes
C10 C11 C2 122.6(3) ?
C10 C11 C9 124.0(3) ?
C2 C11 C9 113.4(3) ?
O2 C14 N1 123.0(3) ?
O2 C14 C13 127.5(3) ?
N1 C14 C13 109.5(3) ?
C12 C13 C14 126.2(3) ?
C12 C13 S1 123.8(3) ?
C14 C13 S1 109.9(2) ?
C3 C2 C11 120.1(3) ?
C3 C2 C1 133.1(3) ?
C11 C2 C1 106.8(3) ?
C2 C3 C4 118.0(4) ?
C2 C3 H3 121.0 ?
C4 C3 H3 121.0 ?
C13 C12 C9 134.6(3) ?
C13 C12 C1 119.1(3) ?
C9 C12 C1 106.3(3) ?
C9 C8 C7 118.5(3) ?
C9 C8 H8 120.8 ?
C7 C8 H8 120.8 ?
C11 C10 C6 116.8(3) ?
C11 C10 C5 116.3(4) ?
C6 C10 C5 126.9(3) ?
N1 C15 S2 127.5(3) ?
N1 C15 S1 110.5(3) ?
S2 C15 S1 122.0(2) ?
C7 C6 C10 119.6(3) ?
C7 C6 H6 120.2 ?
C10 C6 H6 120.2 ?
C5 C4 C3 122.1(4) ?
C5 C4 H4 119.0 ?
C3 C4 H4 119.0 ?
C4 C5 C10 120.9(3) ?
C4 C5 H5 119.5 ?
C10 C5 H5 119.5 ?
C6 C7 C8 123.0(4) ?
C6 C7 H7 118.5 ?
C8 C7 H7 118.5 ?
N1 C16 C17 110.9(3) ?
N1 C16 H16A 109.5 ?
C17 C16 H16A 109.5 ?
N1 C16 H16B 109.5 ?
C17 C16 H16B 109.5 ?
H16A C16 H16B 108.0 ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C13 1.743(4)
S1 C15 1.751(4)
S2 C15 1.626(4)
C9 C8 1.367(5)
C9 C11 1.425(4)
C9 C12 1.486(4)
O2 C14 1.198(4)
O1 C1 1.220(4)
C1 C2 1.463(5)
C1 C12 1.513(5)
N1 C15 1.367(5)
N1 C14 1.390(4)
N1 C16 1.480(5)
C11 C10 1.389(5)
C11 C2 1.408(5)
C14 C13 1.491(5)
C13 C12 1.347(4)
C2 C3 1.365(5)
C3 C4 1.414(5)
C3 H3 0.93
C8 C7 1.420(5)
C8 H8 0.93
C10 C6 1.407(5)
C10 C5 1.421(5)
C6 C7 1.378(5)
C6 H6 0.93
C4 C5 1.360(6)
C4 H4 0.93
C5 H5 0.93
C7 H7 0.93
C16 C17 1.507(5)
C16 H16A 0.97
C16 H16B 0.97
C17 H17A 0.96
C17 H17B 0.96
C17 H17C 0.96
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
C3 H3 O2 4_465 0.93 2.50 3.423(5) 172 yes
C7 H7 O1 4_666 0.93 2.59 3.290(5) 132 yes
C8 H8 O2 . 0.93 2.23 2.952(4) 134 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
C8 C9 C11 C10 0.3(6)
C12 C9 C11 C10 -179.9(3)
C8 C9 C11 C2 -179.3(3)
C12 C9 C11 C2 0.4(4)
C15 N1 C14 O2 178.0(4)
C16 N1 C14 O2 -3.4(5)
C15 N1 C14 C13 -1.6(4)
C16 N1 C14 C13 177.0(3)
O2 C14 C13 C12 2.5(6)
N1 C14 C13 C12 -177.9(3)
O2 C14 C13 S1 -179.7(3)
N1 C14 C13 S1 -0.2(4)
C15 S1 C13 C12 179.1(3)
C15 S1 C13 C14 1.3(3)
C10 C11 C2 C3 0.9(5)
C9 C11 C2 C3 -179.4(3)
C10 C11 C2 C1 -179.1(3)
C9 C11 C2 C1 0.6(4)
O1 C1 C2 C3 -2.1(7)
C12 C1 C2 C3 178.7(4)
O1 C1 C2 C11 177.9(4)
C12 C1 C2 C11 -1.3(4)
C11 C2 C3 C4 0.6(5)
C1 C2 C3 C4 -179.4(3)
C14 C13 C12 C9 -3.2(7)
S1 C13 C12 C9 179.3(3)
C14 C13 C12 C1 177.1(3)
S1 C13 C12 C1 -0.3(5)
C8 C9 C12 C13 -1.2(8)
C11 C9 C12 C13 179.1(4)
C8 C9 C12 C1 178.5(4)
C11 C9 C12 C1 -1.2(4)
O1 C1 C12 C13 2.1(5)
C2 C1 C12 C13 -178.6(3)
O1 C1 C12 C9 -177.7(3)
C2 C1 C12 C9 1.6(4)
C11 C9 C8 C7 -1.5(5)
C12 C9 C8 C7 178.8(4)
C2 C11 C10 C6 -179.9(3)
C9 C11 C10 C6 0.5(5)
C2 C11 C10 C5 -1.4(5)
C9 C11 C10 C5 179.0(3)
C14 N1 C15 S2 -177.9(3)
C16 N1 C15 S2 3.6(5)
C14 N1 C15 S1 2.6(4)
C16 N1 C15 S1 -175.9(3)
C13 S1 C15 N1 -2.1(3)
C13 S1 C15 S2 178.3(2)
C11 C10 C6 C7 0.0(5)
C5 C10 C6 C7 -178.4(4)
C2 C3 C4 C5 -1.6(6)
C3 C4 C5 C10 1.2(6)
C11 C10 C5 C4 0.3(6)
C6 C10 C5 C4 178.7(4)
C10 C6 C7 C8 -1.2(6)
C9 C8 C7 C6 2.0(6)
C15 N1 C16 C17 -93.0(4)
C14 N1 C16 C17 88.5(4)