#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/15/2231539.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_2231539
loop_
_publ_author_name
'Shalini, S.'
'Girija, C. R.'
'Jotani, Mukesh M.'
'Rajashekhar, B.'
'Rao, Nageswar'
'Tiekink, Edward R. T.'
_publ_section_title
;
 (1E,4E)-1,5-Bis(thiophen-3-yl)penta-1,4-dien-3-one
;
_journal_coeditor_code           HG5079
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2354
_journal_paper_doi               10.1107/S160053681103248X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H10 O S2'
_chemical_formula_moiety         'C13 H10 O S2'
_chemical_formula_sum            'C13 H10 O S2'
_chemical_formula_weight         246.33
_chemical_name_systematic
;
(1E,4E)-1,5-Bis(thiophen-3-yl)penta-1,4-dien-3-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c 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            8
_cell_length_a                   11.8908(3)
_cell_length_b                   7.18070(10)
_cell_length_c                   28.3004(6)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      5.0
_cell_volume                     2416.41(9)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            39245
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.44
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.318
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.9807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                2187
_reflns_number_total             2760
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5079.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               2231539
_cod_database_fobs_code          2231539
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, 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_symmetry_multiplicity
S S1 0.38360(5) 0.12409(9) 0.833684(17) 0.0655(2) Uani d . 1 1
S S2 0.38292(5) -0.15855(9) 0.398067(18) 0.0658(2) Uani d . 1 1
O O1 0.17784(11) 0.0181(2) 0.61498(4) 0.0581(4) Uani d . 1 1
C C3 0.35238(14) 0.0577(2) 0.74599(6) 0.0422(4) Uani d . 1 1
C C5 0.29957(15) 0.0511(2) 0.69974(6) 0.0441(4) Uani d . 1 1
H H5 0.2294 0.1072 0.6971 0.053 Uiso calc R 1 1
C C8 0.33643(16) -0.0925(3) 0.57374(6) 0.0476(4) Uani d . 1 1
H H8 0.4061 -0.1500 0.5770 0.057 Uiso calc R 1 1
C C2 0.45551(15) -0.0286(3) 0.75867(6) 0.0516(4) Uani d . 1 1
H H2 0.5002 -0.0944 0.7375 0.062 Uiso calc R 1 1
C C10 0.34646(15) -0.1238(2) 0.48658(6) 0.0462(4) Uani d . 1 1
C C6 0.34072(15) -0.0264(3) 0.66085(6) 0.0467(4) Uani d . 1 1
H H6 0.4121 -0.0794 0.6617 0.056 Uiso calc R 1 1
C C11 0.30593(18) -0.0723(3) 0.44352(7) 0.0569(5) Uani d . 1 1
H H11 0.2427 0.0024 0.4395 0.068 Uiso calc R 1 1
C C9 0.29452(16) -0.0692(3) 0.53080(6) 0.0472(4) Uani d . 1 1
H H9 0.2246 -0.0118 0.5288 0.057 Uiso calc R 1 1
C C4 0.30471(17) 0.1448(3) 0.78394(6) 0.0518(4) Uani d . 1 1
H H4 0.2366 0.2084 0.7827 0.062 Uiso calc R 1 1
C C7 0.27673(15) -0.0308(2) 0.61635(6) 0.0447(4) Uani d . 1 1
C C1 0.48190(17) -0.0050(3) 0.80489(7) 0.0616(5) Uani d . 1 1
H H1 0.5460 -0.0536 0.8191 0.074 Uiso calc R 1 1
C C13 0.44370(16) -0.2385(3) 0.48152(7) 0.0550(5) Uani d . 1 1
H H13 0.4836 -0.2873 0.5069 0.066 Uiso calc R 1 1
C C12 0.47191(17) -0.2690(3) 0.43574(8) 0.0616(5) Uani d . 1 1
H H12 0.5326 -0.3415 0.4261 0.074 Uiso calc R 1 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'
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
C4 S1 C1 91.73(9)
C11 S2 C12 91.76(10)
C4 C3 C2 111.06(16)
C4 C3 C5 122.97(16)
C2 C3 C5 125.93(16)
C6 C5 C3 127.01(17)
C6 C5 H5 116.5
C3 C5 H5 116.5
C9 C8 C7 122.26(17)
C9 C8 H8 118.9
C7 C8 H8 118.9
C1 C2 C3 112.91(18)
C1 C2 H2 123.5
C3 C2 H2 123.5
C11 C10 C13 110.73(17)
C11 C10 C9 123.24(17)
C13 C10 C9 126.03(17)
C5 C6 C7 121.90(17)
C5 C6 H6 119.1
C7 C6 H6 119.1
C10 C11 S2 112.85(15)
C10 C11 H11 123.6
S2 C11 H11 123.6
C8 C9 C10 126.70(17)
C8 C9 H9 116.7
C10 C9 H9 116.7
C3 C4 S1 112.49(15)
C3 C4 H4 123.8
S1 C4 H4 123.8
O1 C7 C8 121.58(16)
O1 C7 C6 121.05(16)
C8 C7 C6 117.36(16)
C2 C1 S1 111.80(15)
C2 C1 H1 124.1
S1 C1 H1 124.1
C12 C13 C10 112.92(18)
C12 C13 H13 123.5
C10 C13 H13 123.5
C13 C12 S2 111.74(16)
C13 C12 H12 124.1
S2 C12 H12 124.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.6982(19)
S1 C1 1.700(2)
S2 C11 1.6960(19)
S2 C12 1.699(2)
O1 C7 1.228(2)
C3 C4 1.366(2)
C3 C2 1.420(2)
C3 C5 1.452(2)
C5 C6 1.327(2)
C5 H5 0.9300
C8 C9 1.324(2)
C8 C7 1.468(2)
C8 H8 0.9300
C2 C1 1.356(3)
C2 H2 0.9300
C10 C11 1.362(3)
C10 C13 1.427(3)
C10 C9 1.450(2)
C6 C7 1.472(2)
C6 H6 0.9300
C11 H11 0.9300
C9 H9 0.9300
C4 H4 0.9300
C1 H1 0.9300
C13 C12 1.356(3)
C13 H13 0.9300
C12 H12 0.9300
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
C1 H1 O1 6_657 0.93 2.49 3.256(2) 140
C12 H12 O1 3_546 0.93 2.44 3.355(2) 169
C2 H2 Cg1 4_646 0.93 2.86 3.671(2) 147
C4 H4 Cg1 7_555 0.93 2.97 3.809(2) 151
C11 H11 Cg2 7_555 0.93 2.83 3.702(2) 156
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
C4 C3 C5 C6 178.38(18)
C2 C3 C5 C6 -4.2(3)
C4 C3 C2 C1 0.2(2)
C5 C3 C2 C1 -177.47(18)
C3 C5 C6 C7 177.39(16)
C13 C10 C11 S2 -0.2(2)
C9 C10 C11 S2 -179.36(15)
C12 S2 C11 C10 0.47(17)
C7 C8 C9 C10 179.69(17)
C11 C10 C9 C8 -170.5(2)
C13 C10 C9 C8 10.5(3)
C2 C3 C4 S1 0.5(2)
C5 C3 C4 S1 178.21(13)
C1 S1 C4 C3 -0.77(16)
C9 C8 C7 O1 11.8(3)
C9 C8 C7 C6 -167.02(17)
C5 C6 C7 O1 -8.4(3)
C5 C6 C7 C8 170.49(17)
C3 C2 C1 S1 -0.7(2)
C4 S1 C1 C2 0.87(17)
C11 C10 C13 C12 -0.2(3)
C9 C10 C13 C12 178.87(18)
C10 C13 C12 S2 0.6(2)
C11 S2 C12 C13 -0.61(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8190391
