#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/42/2224212.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_2224212
loop_
_publ_author_name
'Briggs, Jonathan B.'
'Jia, Wenling'
'Jazdzyk, Mikaël D.'
'Miller, Glen P.'
_publ_section_title
;
 2,5-Dichlorothiophene 1,1-dioxide
;
_journal_coeditor_code           FL2274
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3258
_journal_paper_doi               10.1107/S1600536809050776
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C4 H2 Cl2 O2 S'
_chemical_formula_moiety         'C4 H2 Cl2 O2 S'
_chemical_formula_sum            'C4 H2 Cl2 O2 S'
_chemical_formula_weight         185.02
_chemical_name_systematic
;
2,5-Dichlorothiophene 1,1-dioxide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 90.275(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.588(2)
_cell_length_b                   10.584(3)
_cell_length_c                   8.745(3)
_cell_measurement_reflns_used    1863
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      3.30
_cell_volume                     702.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'GIS (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3352
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_T_max  0.7262
_exptl_absorpt_correction_T_min  0.5896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.314
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     42
_refine_ls_number_reflns         622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0473P)²+0.6008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                549
_reflns_number_total             622
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fl2274.cif
_cod_data_source_block           I
_cod_original_cell_volume        702.4(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2224212
_cod_database_fobs_code          2224212
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.32276(10) 0.08665(9) 0.07774(10) 0.0906(4) Uani d . 1 . .
S S1 0.0000 0.15554(8) 0.2500 0.0529(3) Uani d S 1 . .
O O1 -0.0844(3) 0.2242(2) 0.1299(2) 0.0779(6) Uani d . 1 . .
C C1 0.1415(3) 0.0379(3) 0.1743(3) 0.0582(6) Uani d . 1 . .
C C2 0.0827(4) -0.0754(3) 0.2059(3) 0.0677(8) Uani d . 1 . .
H H2 0.1398 -0.1490 0.1757 0.081 Uiso calc R 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
Cl1 0.0634(5) 0.1157(8) 0.0932(6) 0.0154(4) 0.0365(4) 0.0078(5)
S1 0.0513(5) 0.0506(5) 0.0570(5) 0.000 0.0174(4) 0.000
O1 0.0812(13) 0.0728(12) 0.0799(13) 0.0258(11) 0.0188(10) 0.0181(10)
C1 0.0518(14) 0.0674(15) 0.0553(14) 0.0134(12) 0.0115(11) 0.0005(12)
C2 0.0788(19) 0.0587(15) 0.0657(17) 0.0167(14) 0.0042(14) -0.0020(13)
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
O1 S1 O1 2 . 118.8(2) ?
O1 S1 C1 2 . 111.19(13) ?
O1 S1 C1 . . 110.68(12) ?
O1 S1 C1 2 2 110.68(12) ?
O1 S1 C1 . 2 111.19(13) ?
C1 S1 C1 . 2 90.87(18) ?
C2 C1 Cl1 . . 131.4(2) ?
C2 C1 S1 . . 110.9(2) ?
Cl1 C1 S1 . . 117.74(16) ?
C1 C2 C2 . 2 113.68(16) ?
C1 C2 H2 . . 123.2 ?
C2 C2 H2 2 . 123.2 ?
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
Cl1 C1 . 1.698(3) ?
S1 O1 2 1.427(2) ?
S1 O1 . 1.427(2) ?
S1 C1 . 1.774(2) ?
S1 C1 2 1.774(2) ?
C1 C2 . 1.310(4) ?
C2 C2 2 1.476(6) ?
C2 H2 . 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
C2 H2 O1 3_545 0.93 2.52 3.367(4) 152
