#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/44/2204452.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_2204452
loop_
_publ_author_name
'Xian-Zhong Sun'
'Ming-Hua Zeng'
'Bao-Hui Ye'
_publ_section_title
;
 Linear chains in the 1:1 complex of thiophene-2,5-dicarboxylic acid
 and 4,4'-bipyridine
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2103
_journal_page_last               o2104
_journal_paper_doi               10.1107/S160053680402639X
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C10 H8 N2, C6 H4 O4 S'
_chemical_formula_moiety         'C10 H8 N2, C6 H4 O4 S'
_chemical_formula_sum            'C16 H12 N2 O4 S'
_chemical_formula_weight         328.34
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.718(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8598(6)
_cell_length_b                   10.3438(9)
_cell_length_c                   21.1315(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     1492.0(2)
_computing_cell_refinement       'R3m Software'
_computing_data_collection       'R3m Software (Siemens, 1990)'
_computing_data_reduction        'R3m Software'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens R3m'
_diffrn_measurement_method       ω
_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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8861
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_correction_T_min  0.8857
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0724P)²+0.482P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1448
_reflns_number_gt                2620
_reflns_number_total             3243
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv6003.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204452
_cod_database_fobs_code          2204452
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_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_type_symbol
S1 0.33851(9) 0.33146(5) 0.36381(3) 0.0512(2) Uani d . 1 S
O1 0.0293(3) 0.27661(18) 0.44562(8) 0.0639(5) Uani d . 1 O
H1A -0.0589 0.2579 0.4675 0.096 Uiso calc R 1 H
O2 -0.1340(3) 0.4639(2) 0.43246(9) 0.0711(5) Uani d . 1 O
O3 0.6885(3) 0.31486(16) 0.28917(10) 0.0689(5) Uani d . 1 O
O4 0.6846(2) 0.52304(15) 0.26145(8) 0.0560(4) Uani d . 1 O
H4B 0.7831 0.5031 0.2446 0.084 Uiso calc R 1 H
N1 0.0053(3) 0.97041(18) 0.29659(8) 0.0449(4) Uani d . 1 N
N2 -0.7472(3) 0.7996(2) 0.48496(9) 0.0604(6) Uani d . 1 N
C1 -0.2355(3) 1.0308(2) 0.36496(10) 0.0470(5) Uani d . 1 C
H1B -0.2952 1.0963 0.3862 0.056 Uiso calc R 1 H
C2 -0.0833(3) 1.0590(2) 0.32885(11) 0.0473(5) Uani d . 1 C
H2B -0.0412 1.1443 0.3271 0.057 Uiso calc R 1 H
C3 -0.0590(3) 0.8489(2) 0.29852(11) 0.0498(6) Uani d . 1 C
H3A -0.0011 0.7864 0.2749 0.060 Uiso calc R 1 H
C4 -0.2075(3) 0.8121(2) 0.33394(11) 0.0492(5) Uani d . 1 C
H4A -0.2472 0.7261 0.3344 0.059 Uiso calc R 1 H
C5 -0.2977(3) 0.9042(2) 0.36905(9) 0.0406(5) Uani d . 1 C
C6 -0.4538(3) 0.8681(2) 0.40956(10) 0.0432(5) Uani d . 1 C
C7 -0.4479(4) 0.7505(2) 0.44161(11) 0.0539(6) Uani d . 1 C
H7A -0.3452 0.6929 0.4384 0.065 Uiso calc R 1 H
C8 -0.5986(4) 0.7209(3) 0.47847(12) 0.0601(7) Uani d . 1 C
H8A -0.5949 0.6419 0.4996 0.072 Uiso calc R 1 H
C9 -0.7522(4) 0.9121(3) 0.45458(12) 0.0625(7) Uani d . 1 C
H9A -0.8563 0.9679 0.4590 0.075 Uiso calc R 1 H
C10 -0.6097(3) 0.9497(3) 0.41673(11) 0.0546(6) Uani d . 1 C
H10A -0.6183 1.0294 0.3962 0.066 Uiso calc R 1 H
C11 0.0010(3) 0.3943(2) 0.42296(11) 0.0515(6) Uani d . 1 C
C12 0.1569(3) 0.4341(2) 0.38291(10) 0.0453(5) Uani d . 1 C
C13 0.1743(3) 0.5525(2) 0.35691(11) 0.0518(6) Uani d . 1 C
H13A 0.0885 0.6204 0.3622 0.062 Uiso calc R 1 H
C14 0.3363(3) 0.5623(2) 0.32102(11) 0.0479(5) Uani d . 1 C
H14A 0.3690 0.6370 0.3000 0.057 Uiso calc R 1 H
C15 0.4386(3) 0.45029(19) 0.32068(10) 0.0408(5) Uani d . 1 C
C16 0.6172(3) 0.4214(2) 0.28896(11) 0.0439(5) Uani d . 1 C
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'
N N 0.0061 0.0033 '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
C15 S1 C12 91.15(10)
C11 O1 H1A 109.5
C16 O4 H4B 109.5
C2 N1 C3 117.75(18)
C8 N2 C9 118.2(2)
C5 C1 C2 119.25(19)
C5 C1 H1B 120.4
C2 C1 H1B 120.4
N1 C2 C1 123.2(2)
N1 C2 H2B 118.4
C1 C2 H2B 118.4
N1 C3 C4 122.8(2)
N1 C3 H3A 118.6
C4 C3 H3A 118.6
C3 C4 C5 119.6(2)
C3 C4 H4A 120.2
C5 C4 H4A 120.2
C1 C5 C4 117.33(19)
C1 C5 C6 121.27(19)
C4 C5 C6 121.4(2)
C10 C6 C7 117.8(2)
C10 C6 C5 121.3(2)
C7 C6 C5 120.9(2)
C8 C7 C6 118.6(2)
C8 C7 H7A 120.7
C6 C7 H7A 120.7
N2 C8 C7 123.1(2)
N2 C8 H8A 118.4
C7 C8 H8A 118.4
N2 C9 C10 122.8(2)
N2 C9 H9A 118.6
C10 C9 H9A 118.6
C9 C10 C6 119.5(2)
C9 C10 H10A 120.3
C6 C10 H10A 120.3
O2 C11 O1 125.4(2)
O2 C11 C12 122.5(2)
O1 C11 C12 112.1(2)
C13 C12 C11 125.5(2)
C13 C12 S1 111.66(16)
C11 C12 S1 122.88(18)
C12 C13 C14 112.9(2)
C12 C13 H13A 123.5
C14 C13 H13A 123.5
C15 C14 C13 112.2(2)
C15 C14 H14A 123.9
C13 C14 H14A 123.9
C14 C15 C16 128.77(19)
C14 C15 S1 112.01(15)
C16 C15 S1 119.22(16)
O3 C16 O4 125.1(2)
O3 C16 C15 122.38(19)
O4 C16 C15 112.52(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C15 1.714(2)
S1 C12 1.716(2)
O1 C11 1.316(3)
O1 H1A 0.8200
O2 C11 1.206(3)
O3 C16 1.205(3)
O4 C16 1.308(2)
O4 H4B 0.8200
N1 C2 1.326(3)
N1 C3 1.334(3)
N2 C8 1.322(3)
N2 C9 1.327(3)
C1 C5 1.383(3)
C1 C2 1.384(3)
C1 H1B 0.9300
C2 H2B 0.9300
C3 C4 1.376(3)
C3 H3A 0.9300
C4 C5 1.390(3)
C4 H4A 0.9300
C5 C6 1.484(3)
C6 C10 1.383(3)
C6 C7 1.391(3)
C7 C8 1.390(3)
C7 H7A 0.9300
C8 H8A 0.9300
C9 C10 1.380(3)
C9 H9A 0.9300
C10 H10A 0.9300
C11 C12 1.486(3)
C12 C13 1.352(3)
C13 C14 1.410(3)
C13 H13A 0.9300
C14 C15 1.355(3)
C14 H14A 0.9300
C15 C16 1.484(3)
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
O1 H1A N2 3_466 0.82 1.84 2.662(2) 175
O4 H4B N1 2_645 0.82 1.80 2.616(2) 175
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130343
