#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/77/2227731.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_2227731
loop_
_publ_author_name
'Harrison, William T. A.'
'Chidan Kumar, C. S.'
'Yathirajan, H. S.'
'Mayekar, A. N.'
'Narayana, B.'
_publ_section_title
;
 1-(2,5-Dichloro-3-thienyl)ethanone: infinite sheets mediated by
 O···Cl halogen bonds
;
_journal_coeditor_code           JJ2050
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2480
_journal_paper_doi               10.1107/S1600536810035154
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H4 Cl2 O S'
_chemical_formula_moiety         'C6 H4 Cl2 O S'
_chemical_formula_sum            'C6 H4 Cl2 O S'
_chemical_formula_weight         195.05
_chemical_name_systematic
;
1-(2,5-Dichloro-3-thienyl)ethanone
;
_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                   13.0980(3)
_cell_length_b                   7.17900(10)
_cell_length_c                   16.3290(3)
_cell_measurement_reflns_used    12696
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1535.42(5)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor 1997), and SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12928
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    1.038
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0312
_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)+(0.0196P)²+1.1699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                1538
_reflns_number_total             1758
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jj2050.cif
_cod_data_source_block           I
_cod_database_code               2227731
_cod_database_fobs_code          2227731
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
C C1 0.36993(13) 0.4974(3) 0.44792(10) 0.0181(4) Uani d . 1 . .
C C2 0.36763(13) 0.5824(2) 0.52170(11) 0.0178(4) Uani d . 1 . .
H H2 0.3618 0.7134 0.5285 0.021 Uiso calc R 1 . .
C C3 0.37494(12) 0.4537(2) 0.58881(10) 0.0153(4) Uani d . 1 . .
C C4 0.38165(13) 0.2736(2) 0.56061(11) 0.0172(4) Uani d . 1 . .
C C5 0.37563(13) 0.5245(3) 0.67461(11) 0.0181(4) Uani d . 1 . .
C C6 0.37733(14) 0.3927(3) 0.74569(11) 0.0227(4) Uani d . 1 . .
H H6A 0.3730 0.4634 0.7969 0.034 Uiso calc R 1 . .
H H6B 0.4410 0.3210 0.7448 0.034 Uiso calc R 1 . .
H H6C 0.3191 0.3074 0.7418 0.034 Uiso calc R 1 . .
O O1 0.37515(11) 0.69263(19) 0.68546(8) 0.0299(3) Uani d . 1 . .
S S1 0.38011(3) 0.25777(6) 0.45563(3) 0.02062(14) Uani d . 1 . .
Cl Cl1 0.36483(4) 0.60020(7) 0.35316(3) 0.02524(14) Uani d . 1 . .
Cl Cl2 0.39243(4) 0.06821(6) 0.61358(3) 0.02400(14) Uani d . 1 . .
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
C1 0.0175(9) 0.0234(10) 0.0134(9) -0.0004(7) -0.0011(6) 0.0017(7)
C2 0.0191(9) 0.0176(8) 0.0168(9) 0.0001(7) 0.0000(7) 0.0017(7)
C3 0.0154(8) 0.0162(8) 0.0144(9) 0.0004(6) 0.0010(6) 0.0010(7)
C4 0.0174(9) 0.0179(8) 0.0163(8) -0.0007(7) 0.0008(7) 0.0006(7)
C5 0.0190(9) 0.0198(8) 0.0154(9) 0.0003(7) 0.0005(6) -0.0007(7)
C6 0.0310(11) 0.0227(10) 0.0145(10) 0.0001(7) 0.0021(7) 0.0022(7)
O1 0.0548(10) 0.0174(7) 0.0175(7) 0.0006(6) -0.0007(6) -0.0024(6)
S1 0.0244(3) 0.0215(3) 0.0160(3) -0.00193(17) 0.00004(17) -0.00486(17)
Cl1 0.0251(3) 0.0372(3) 0.0134(2) 0.00171(19) -0.00100(16) 0.00583(18)
Cl2 0.0332(3) 0.0138(2) 0.0250(3) 0.00051(17) -0.00035(19) 0.00208(17)
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 Cl1 . . 127.54(15) ?
C2 C1 S1 . . 112.71(13) ?
Cl1 C1 S1 . . 119.75(10) ?
C1 C2 C3 . . 112.84(16) ?
C1 C2 H2 . . 123.6 ?
C3 C2 H2 . . 123.6 ?
C4 C3 C2 . . 110.71(15) ?
C4 C3 C5 . . 129.40(16) ?
C2 C3 C5 . . 119.88(15) ?
C3 C4 Cl2 . . 130.13(14) ?
C3 C4 S1 . . 113.28(13) ?
Cl2 C4 S1 . . 116.58(10) ?
O1 C5 C3 . . 118.28(16) ?
O1 C5 C6 . . 120.83(16) ?
C3 C5 C6 . . 120.88(16) ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C4 S1 C1 . . 90.45(8) ?
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
C1 C2 . 1.351(2) ?
C1 Cl1 . 1.7156(18) ?
C1 S1 . 1.7303(19) ?
C2 C3 . 1.437(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.376(2) ?
C3 C5 . 1.490(2) ?
C4 Cl2 . 1.7151(18) ?
C4 S1 . 1.7181(19) ?
C5 O1 . 1.220(2) ?
C5 C6 . 1.498(2) ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
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
Cl1 C1 C2 C3 . . . . -179.10(13) ?
S1 C1 C2 C3 . . . . 0.4(2) ?
C1 C2 C3 C4 . . . . -0.5(2) ?
C1 C2 C3 C5 . . . . 178.80(15) ?
C2 C3 C4 Cl2 . . . . 179.62(14) ?
C5 C3 C4 Cl2 . . . . 0.4(3) ?
C2 C3 C4 S1 . . . . 0.40(19) ?
C5 C3 C4 S1 . . . . -178.85(14) ?
C4 C3 C5 O1 . . . . 175.49(17) ?
C2 C3 C5 O1 . . . . -3.7(3) ?
C4 C3 C5 C6 . . . . -4.2(3) ?
C2 C3 C5 C6 . . . . 176.57(15) ?
C3 C4 S1 C1 . . . . -0.14(14) ?
Cl2 C4 S1 C1 . . . . -179.47(11) ?
C2 C1 S1 C4 . . . . -0.18(14) ?
Cl1 C1 S1 C4 . . . . 179.40(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 106264
