#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/16/7221633.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_7221633
loop_
_publ_author_name
'Madabhushi, Sridhar'
'Kurva, Srinivas'
'Sriramoju, Vinodkumar'
'Nanubolu, Jagadeesh babu'
'Cirandur, Suresh Reddy'
_publ_section_title
;
 Efficient synthesis of polyfunctionalized thiophene-2,3-diones and
 thiophen-3(2H)-ones using β-oxodithioesters
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA11629E
_journal_year                    2015
_chemical_formula_moiety         'C12 H9 Cl O2 S2'
_chemical_formula_sum            'C12 H9 Cl O2 S2'
_chemical_formula_weight         284.76
_chemical_name_systematic
;
4-(4-chlorobenzoyl)-5-(methylthio)-thiophen-2(2H)-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
_audit_update_record
;
2015-05-26 deposited with the CCDC.
2015-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.1680(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2624(8)
_cell_length_b                   13.4433(9)
_cell_length_c                   7.9968(5)
_cell_measurement_reflns_used    9189
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.30
_cell_volume                     1266.11(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11867
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  0.8367
_exptl_absorpt_correction_T_min  0.7689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.4969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0955
_reflns_number_gt                2099
_reflns_number_total             2225
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra11629e2.cif
_cod_data_source_block           ax81
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c  '
_cod_database_code               7221633
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_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
C1 C 0.51848(19) 0.8491(2) 0.1490(4) 0.0723(7) Uani 1 1 d .
C2 C 0.5407(2) 0.9423(2) 0.2186(4) 0.0794(8) Uani 1 1 d .
H2 H 0.4834 0.9799 0.2432 0.095 Uiso 1 1 calc R
C3 C 0.64958(18) 0.97989(19) 0.2517(3) 0.0649(6) Uani 1 1 d .
H3 H 0.6651 1.0440 0.2955 0.078 Uiso 1 1 calc R
C4 C 0.73588(16) 0.92282(15) 0.2201(3) 0.0494(4) Uani 1 1 d .
C5 C 0.71092(17) 0.82895(16) 0.1484(3) 0.0544(5) Uani 1 1 d .
H5 H 0.7681 0.7903 0.1257 0.065 Uiso 1 1 calc R
C6 C 0.6011(2) 0.79243(18) 0.1103(3) 0.0650(6) Uani 1 1 d .
H6 H 0.5836 0.7302 0.0590 0.078 Uiso 1 1 calc R
C7 C 0.85101(16) 0.96853(14) 0.2526(3) 0.0482(4) Uani 1 1 d .
C8 C 0.95402(15) 0.90899(13) 0.3132(2) 0.0424(4) Uani 1 1 d .
C9 C 1.05727(15) 0.94340(12) 0.2994(2) 0.0397(4) Uani 1 1 d .
C10 C 1.08509(18) 0.77543(15) 0.4509(3) 0.0567(5) Uani 1 1 d .
H10A H 1.0872 0.7111 0.3968 0.068 Uiso 1 1 calc R
H10B H 1.1141 0.7676 0.5760 0.068 Uiso 1 1 calc R
C11 C 0.96444(17) 0.81415(14) 0.4045(2) 0.0473(4) Uani 1 1 d .
C12 C 1.22739(19) 1.05112(17) 0.2251(3) 0.0642(6) Uani 1 1 d .
H12A H 1.2719 1.0444 0.3440 0.096 Uiso 1 1 calc R
H12B H 1.2487 1.1111 0.1770 0.096 Uiso 1 1 calc R
H12C H 1.2406 0.9950 0.1591 0.096 Uiso 1 1 calc R
Cl1 Cl 0.38168(6) 0.80153(8) 0.10900(16) 0.1256(4) Uani 1 1 d .
O1 O 0.85773(13) 1.05771(10) 0.2242(3) 0.0691(5) Uani 1 1 d .
O2 O 0.89125(14) 0.76873(11) 0.4483(2) 0.0634(4) Uani 1 1 d .
S1 S 1.17060(4) 0.86294(4) 0.37443(7) 0.05026(17) Uani 1 1 d .
S2 S 1.07969(4) 1.05662(3) 0.21590(7) 0.04840(17) Uani 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'
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
C2 C1 C6 121.7(2)
C2 C1 Cl1 119.0(2)
C6 C1 Cl1 119.3(2)
C1 C2 C3 119.0(2)
C1 C2 H2 120.5
C3 C2 H2 120.5
C2 C3 C4 120.6(2)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 119.21(19)
C5 C4 C7 122.40(17)
C3 C4 C7 118.22(18)
C4 C5 C6 120.2(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 119.2(2)
C1 C6 H6 120.4
C5 C6 H6 120.4
O1 C7 C8 120.05(17)
O1 C7 C4 118.57(18)
C8 C7 C4 121.37(17)
C9 C8 C11 112.26(16)
C9 C8 C7 121.18(17)
C11 C8 C7 126.39(16)
C8 C9 S2 125.34(14)
C8 C9 S1 115.36(13)
S2 C9 S1 119.30(10)
C11 C10 S1 108.39(13)
C11 C10 H10A 110.0
S1 C10 H10A 110.0
C11 C10 H10B 110.0
S1 C10 H10B 110.0
H10A C10 H10B 108.4
O2 C11 C8 127.99(19)
O2 C11 C10 120.44(18)
C8 C11 C10 111.52(16)
S2 C12 H12A 109.5
S2 C12 H12B 109.5
H12A C12 H12B 109.5
S2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C9 S1 C10 92.23(9)
C9 S2 C12 102.53(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.367(4)
C1 C6 1.370(4)
C1 Cl1 1.740(2)
C2 C3 1.383(3)
C2 H2 0.9300
C3 C4 1.386(3)
C3 H3 0.9300
C4 C5 1.385(3)
C4 C7 1.495(3)
C5 C6 1.385(3)
C5 H5 0.9300
C6 H6 0.9300
C7 O1 1.227(2)
C7 C8 1.459(3)
C8 C9 1.381(2)
C8 C11 1.457(3)
C9 S2 1.7146(17)
C9 S1 1.7311(18)
C10 C11 1.514(3)
C10 S1 1.793(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 O2 1.215(2)
C12 S2 1.794(2)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
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
C6 C1 C2 C3 -0.5(5)
Cl1 C1 C2 C3 179.5(2)
C1 C2 C3 C4 -2.0(4)
C2 C3 C4 C5 2.5(4)
C2 C3 C4 C7 177.9(2)
C3 C4 C5 C6 -0.6(3)
C7 C4 C5 C6 -175.8(2)
C2 C1 C6 C5 2.4(4)
Cl1 C1 C6 C5 -177.58(19)
C4 C5 C6 C1 -1.8(4)
C5 C4 C7 O1 140.9(2)
C3 C4 C7 O1 -34.3(3)
C5 C4 C7 C8 -37.7(3)
C3 C4 C7 C8 147.0(2)
O1 C7 C8 C9 -16.1(3)
C4 C7 C8 C9 162.56(17)
O1 C7 C8 C11 158.7(2)
C4 C7 C8 C11 -22.6(3)
C11 C8 C9 S2 -174.54(13)
C7 C8 C9 S2 1.0(3)
C11 C8 C9 S1 5.4(2)
C7 C8 C9 S1 -179.11(14)
C9 C8 C11 O2 174.14(19)
C7 C8 C11 O2 -1.1(3)
C9 C8 C11 C10 -3.3(2)
C7 C8 C11 C10 -178.59(18)
S1 C10 C11 O2 -177.61(15)
S1 C10 C11 C8 0.1(2)
C8 C9 S1 C10 -4.56(15)
S2 C9 S1 C10 175.36(12)
C11 C10 S1 C9 2.34(15)
C8 C9 S2 C12 -177.04(16)
S1 C9 S2 C12 3.05(14)
