#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/44/4114456.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_4114456
loop_
_publ_author_name
'Hong Meng'
'Dmitrii F. Perepichka'
'Michael Bendikov'
'Fred Wudl'
'Grant Z. Pan'
'Wenjiang Yu'
'Wenjian Dong'
'Stuart Brown'
_publ_section_title
;
 Solid-State Synthesis of a Conducting Polythiophene via an Unprecedented
 Heterocyclic Coupling Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15151
_journal_page_last               15162
_journal_paper_doi               10.1021/ja037115y
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C6 H4 Cl2 O2 S'
_chemical_formula_weight         211.05
_chemical_name_systematic
; 
 ? 
;
_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                 93.751(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1098(8)
_cell_length_b                   7.7988(12)
_cell_length_c                   20.306(3)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.64
_cell_measurement_theta_min      3.01
_cell_volume                     807.5(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5066
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        -0.0178
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.5257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             424
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .4
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.1761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                1484
_reflns_number_total             1943
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja037115ysi20030707_023857.cif
_cod_data_source_block           sad
_cod_database_code               4114456
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
Cl1 Cl 0.74113(15) 0.02396(8) 0.42446(3) 0.0836(3) Uani 1 1 d .
Cl2 Cl 1.36029(14) 0.63841(10) 0.41206(3) 0.0825(3) Uani 1 1 d .
S1 S 1.12488(12) 0.30830(8) 0.45301(3) 0.0645(2) Uani 1 1 d .
O1 O 0.6326(3) 0.25930(17) 0.30051(7) 0.0537(4) Uani 1 1 d .
O2 O 0.9445(3) 0.56749(17) 0.29275(7) 0.0516(3) Uani 1 1 d .
C1 C 0.8787(4) 0.2138(3) 0.40337(10) 0.0520(5) Uani 1 1 d .
C2 C 0.8167(3) 0.3058(2) 0.34802(9) 0.0430(4) Uani 1 1 d .
C3 C 0.5756(4) 0.3933(3) 0.25270(10) 0.0520(5) Uani 1 1 d .
H3A H 0.4572 0.4758 0.2706 0.062 Uiso 1 1 calc R
H3B H 0.4886 0.3442 0.2132 0.062 Uiso 1 1 calc R
C4 C 0.8208(4) 0.4830(3) 0.23504(10) 0.0493(4) Uani 1 1 d .
H4A H 0.9413 0.4005 0.2180 0.059 Uiso 1 1 calc R
H4B H 0.7782 0.5672 0.2008 0.059 Uiso 1 1 calc R
C5 C 0.9715(3) 0.4568(2) 0.34438(9) 0.0435(4) Uani 1 1 d .
C6 C 1.1435(4) 0.4746(3) 0.39771(10) 0.0536(5) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.1114(6) 0.0555(4) 0.0822(4) 0.0242(3) -0.0080(4) -0.0246(3)
Cl2 0.0809(5) 0.0896(5) 0.0762(4) -0.0108(3) -0.0019(3) -0.0447(4)
S1 0.0700(4) 0.0696(4) 0.0522(3) 0.0054(3) -0.0085(2) -0.0104(3)
O1 0.0555(8) 0.0449(7) 0.0591(8) 0.0058(6) -0.0074(6) -0.0142(6)
O2 0.0550(8) 0.0404(7) 0.0593(8) 0.0055(6) 0.0038(6) -0.0088(6)
C1 0.0602(12) 0.0427(10) 0.0527(11) 0.0037(8) 0.0008(9) -0.0068(8)
C2 0.0430(9) 0.0368(9) 0.0493(9) -0.0007(7) 0.0034(7) -0.0026(7)
C3 0.0470(11) 0.0524(11) 0.0557(11) 0.0059(9) -0.0036(8) -0.0011(8)
C4 0.0466(10) 0.0483(10) 0.0530(10) 0.0054(8) 0.0030(8) 0.0024(8)
C5 0.0428(9) 0.0388(9) 0.0495(10) 0.0000(8) 0.0083(7) -0.0024(7)
C6 0.0504(11) 0.0543(11) 0.0560(11) -0.0047(9) 0.0035(9) -0.0134(9)
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
C6 S1 C1 90.56(9)
C2 O1 C3 112.73(14)
C5 O2 C4 110.57(14)
C2 C1 Cl1 126.21(16)
C2 C1 S1 112.40(15)
Cl1 C1 S1 121.39(12)
O1 C2 C1 124.38(17)
O1 C2 C5 123.21(16)
C1 C2 C5 112.40(17)
O1 C3 C4 111.34(16)
O2 C4 C3 110.19(16)
C6 C5 O2 125.39(17)
C6 C5 C2 112.11(17)
O2 C5 C2 122.50(16)
C5 C6 Cl2 126.39(16)
C5 C6 S1 112.53(14)
Cl2 C6 S1 121.08(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.706(2)
Cl2 C6 1.704(2)
S1 C6 1.722(2)
S1 C1 1.725(2)
O1 C2 1.352(2)
O1 C3 1.443(2)
O2 C5 1.358(2)
O2 C4 1.453(2)
C1 C2 1.353(3)
C2 C5 1.423(2)
C3 C4 1.499(3)
C5 C6 1.356(3)
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 S1 C1 C2 -0.06(17)
C6 S1 C1 Cl1 179.14(15)
C3 O1 C2 C1 170.30(19)
C3 O1 C2 C5 -11.1(2)
Cl1 C1 C2 O1 0.1(3)
S1 C1 C2 O1 179.22(14)
Cl1 C1 C2 C5 -178.71(15)
S1 C1 C2 C5 0.4(2)
C2 O1 C3 C4 41.0(2)
C5 O2 C4 C3 50.6(2)
O1 C3 C4 O2 -62.9(2)
C4 O2 C5 C6 158.90(19)
C4 O2 C5 C2 -21.2(2)
O1 C2 C5 C6 -179.52(17)
C1 C2 C5 C6 -0.7(2)
O1 C2 C5 O2 0.6(3)
C1 C2 C5 O2 179.38(17)
O2 C5 C6 Cl2 0.4(3)
C2 C5 C6 Cl2 -179.45(15)
O2 C5 C6 S1 -179.43(14)
C2 C5 C6 S1 0.7(2)
C1 S1 C6 C5 -0.36(17)
C1 S1 C6 Cl2 179.76(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11212753
