#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/91/2009189.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_2009189
loop_
_publ_author_name
'Lough, Alan J.'
'Gregson, Richard M.'
'Ferguson, George'
'Glidewell, Christopher'
_publ_section_title
;
 Centrosymmetric molecular strings in the hydrogen-bonded structure of
 4,4'-bipyridyl--4,4'-thiodiphenol (3/2)
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1890
_journal_page_last               1892
_journal_paper_doi               10.1107/S0108270199008963
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         '3C10 H8 N2, 2C12 H10 O2 S'
_chemical_formula_sum            'C54 H44 N6 O4 S2'
_chemical_formula_weight         905.09
_chemical_name_systematic
;
4,4'-Bipyridyl--4,4--thiodiphenol (3/2)
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 128.311(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   19.7378(10)
_cell_length_b                   5.5717(2)
_cell_length_c                   25.6759(11)
_cell_measurement_reflns_used    5045
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      4.18
_cell_volume                     2215.60(19)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa-CCD server software (Nonius, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and  PLATON (Spek, 1999)'
_computing_publication_material
'SHELXL-97 and WordPerfect macro PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  Kappa-CCD
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.070
_diffrn_reflns_av_sigmaI/netI    0.0656
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            22794
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         4.18
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.9604
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.297
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0524P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                3338
_reflns_number_total             5045
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1306.cif
_cod_data_source_block           9914
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2215.60(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2009189
_cod_database_fobs_code          2009189
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 .43135(3) -.45949(8) .81231(2) .02967(13) Uani d . 1 . . S
O24 .15389(7) -.5768(2) .83752(6) .0278(3) Uani d . 1 . . O
O14 .26686(8) .0106(2) .55164(6) .0335(3) Uani d . 1 . . O
C11 .37956(10) -.3133(3) .73439(8) .0244(4) Uani d . 1 . . C
C12 .30727(11) -.4114(3) .67587(8) .0272(4) Uani d . 1 . . C
C13 .26996(11) -.3008(3) .61523(8) .0283(4) Uani d . 1 . . C
C14 .30545(10) -.0902(3) .61240(8) .0243(4) Uani d . 1 . . C
C15 .37786(10) .0097(3) .67081(8) .0254(4) Uani d . 1 . . C
C16 .41375(10) -.0999(3) .73117(8) .0253(4) Uani d . 1 . . C
C21 .34577(10) -.4878(3) .81755(8) .0236(4) Uani d . 1 . . C
C22 .33042(10) -.3074(3) .84665(8) .0254(4) Uani d . 1 . . C
C23 .26670(11) -.3319(3) .85367(8) .0247(4) Uani d . 1 . . C
C24 .21626(10) -.5403(3) .83114(8) .0227(4) Uani d . 1 . . C
C25 .23058(11) -.7197(3) .80144(8) .0252(4) Uani d . 1 . . C
C26 .29509(11) -.6949(3) .79505(8) .0257(4) Uani d . 1 . . C
N31 .36245(9) .3274(2) .53972(7) .0269(3) Uani d . 1 . . N
C32 .36661(12) .2029(3) .49743(8) .0324(4) Uani d . 1 . . C
C33 .41839(12) .2618(3) .48040(8) .0323(4) Uani d . 1 . . C
C34 .47100(10) .4645(3) .50803(8) .0221(4) Uani d . 1 . . C
C35 .46587(11) .5964(3) .55136(8) .0285(4) Uani d . 1 . . C
C36 .41225(11) .5234(3) .56599(9) .0300(4) Uani d . 1 . . C
N41 .10518(9) -.1765(2) .86438(7) .0274(3) Uani d . 1 . . N
C42 .14909(11) -.0580(3) .92227(8) .0277(4) Uani d . 1 . . C
C43 .11411(11) .1247(3) .93511(8) .0264(4) Uani d . 1 . . C
C44 .02896(10) .1951(3) .88630(8) .0238(4) Uani d . 1 . . C
C45 -.01617(11) .0748(3) .82563(8) .0286(4) Uani d . 1 . . C
C46 .02365(11) -.1065(3) .81709(8) .0302(4) Uani d . 1 . . C
N51 -.08844(11) .7528(3) .92283(8) .0365(4) Uani d . 1 . . N
C52 -.13524(12) .5788(3) .87811(10) .0358(5) Uani d . 1 . . C
C53 -.10107(12) .3955(3) .86439(9) .0305(4) Uani d . 1 . . C
C54 -.01216(11) .3869(3) .89846(8) .0250(4) Uani d . 1 . . C
C55 .03717(12) .5641(3) .94574(8) .0281(4) Uani d . 1 . . C
C56 -.00304(12) .7404(3) .95582(9) .0333(4) Uani d . 1 . . C
H24 .1456 -.4494 .8503 .042 Uiso calc R 1 . . H
H14 .2980 .1221 .5550 .050 Uiso calc R 1 . . H
H12 .2831 -.5561 .6774 .033 Uiso calc R 1 . . H
H13 .2202 -.3688 .5757 .034 Uiso calc R 1 . . H
H15 .4026 .1530 .6692 .030 Uiso calc R 1 . . H
H16 .4623 -.0289 .7709 .030 Uiso calc R 1 . . H
H22 .3643 -.1653 .8619 .030 Uiso calc R 1 . . H
H23 .2572 -.2074 .8737 .030 Uiso calc R 1 . . H
H25 .1960 -.8605 .7854 .030 Uiso calc R 1 . . H
H26 .3048 -.8198 .7752 .031 Uiso calc R 1 . . H
H32 .3314 .0639 .4777 .039 Uiso calc R 1 . . H
H33 .4183 .1646 .4499 .039 Uiso calc R 1 . . H
H35 .4994 .7381 .5712 .034 Uiso calc R 1 . . H
H36 .4108 .6171 .5962 .036 Uiso calc R 1 . . H
H42 .2074 -.1023 .9563 .033 Uiso calc R 1 . . H
H43 .1480 .2023 .9771 .032 Uiso calc R 1 . . H
H45 -.0742 .1177 .7903 .034 Uiso calc R 1 . . H
H46 -.0085 -.1861 .7754 .036 Uiso calc R 1 . . H
H52 -.1960 .5815 .8542 .043 Uiso calc R 1 . . H
H53 -.1378 .2769 .8322 .037 Uiso calc R 1 . . H
H55 .0982 .5642 .9710 .034 Uiso calc R 1 . . H
H56 .0322 .8601 .9882 .040 Uiso calc R 1 . . H
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 S1 C21 . 102.38(7) y
S1 C11 C12 . 121.60(10) no
S1 C11 C16 . 119.60(10) no
C12 C11 C16 . 118.8(2) no
C11 C12 C13 . 120.9(2) no
C12 C13 C14 . 119.9(2) no
O14 C14 C13 . 117.70(10) y
O14 C14 C15 . 122.70(10) y
C13 C14 C15 . 119.60(10) no
C14 C15 C16 . 120.0(2) no
C11 C16 C15 . 120.8(2) no
C22 C21 C26 . 118.7(2) no
S1 C21 C22 . 120.50(10) no
S1 C21 C26 . 120.80(10) no
C21 C22 C23 . 121.1(2) no
C22 C23 C24 . 119.90(10) no
O24 C24 C25 . 117.90(10) y
O24 C24 C23 . 122.8(2) y
C23 C24 C25 . 119.3(2) no
C24 C25 C26 . 120.5(2) no
C21 C26 C25 . 120.5(2) no
C32 N31 C36 . 116.0(2) y
N31 C32 C33 . 124.5(2) no
C32 C33 C34 . 119.8(2) no
C33 C34 C35 . 115.8(2) no
C34 C34 C35 3_666 122.1(2) no
C33 C34 C34 3_666 122.1(2) no
C34 C35 C36 . 120.6(2) no
N31 C36 C35 . 123.3(2) no
C42 N41 C46 . 116.7(2) y
N41 C42 C43 . 123.6(2) no
C42 C43 C44 . 119.8(2) no
C43 C44 C45 . 116.7(2) no
C43 C44 C54 . 121.6(2) no
C45 C44 C54 . 121.7(2) no
C44 C45 C46 . 119.8(2) no
N41 C46 C45 . 123.5(2) no
C52 N51 C56 . 115.7(2) y
N51 C52 C53 . 124.5(2) no
C52 C53 C54 . 119.2(2) no
C53 C54 C55 . 116.9(2) no
C44 C54 C55 . 121.1(2) no
C44 C54 C53 . 122.1(2) no
C54 C55 C56 . 119.7(2) no
N51 C56 C55 . 124.1(2) no
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
S1 C11 . 1.782(2) y
S1 C21 . 1.783(2) y
O14 C14 . 1.363(2) y
O24 C24 . 1.354(2) y
C11 C12 . 1.391(2) no
C11 C16 . 1.395(2) no
C12 C13 . 1.387(2) no
C13 C14 . 1.392(2) no
C14 C15 . 1.394(2) no
C15 C16 . 1.384(2) no
C21 C22 . 1.393(2) no
C21 C26 . 1.396(2) no
C22 C23 . 1.383(2) no
C23 C24 . 1.400(2) no
C24 C25 . 1.388(2) no
C25 C26 . 1.388(2) no
N31 C32 . 1.333(2) y
N31 C36 . 1.338(2) y
C32 C33 . 1.377(2) no
C33 C34 . 1.394(2) no
C34 C35 . 1.389(2) no
C34 C34 3_666 1.491(3) no
C35 C36 . 1.386(2) no
N41 C42 . 1.342(2) y
N41 C46 . 1.339(2) y
C42 C43 . 1.380(2) no
C43 C44 . 1.392(2) no
C44 C45 . 1.396(2) no
C44 C54 . 1.488(2) no
C45 C46 . 1.378(2) no
N51 C52 . 1.340(2) y
N51 C56 . 1.339(2) y
C52 C53 . 1.385(2) no
C53 C54 . 1.394(2) no
C54 C55 . 1.389(2) no
C55 C56 . 1.384(2) no
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
_geom_hbond_publ_flag
O14 H14 N31 . 0.84 1.92 2.736(2) 162 yes
O24 H24 N41 . 0.84 1.85 2.683(2) 169 yes
C43 H43 O14 4 0.95 2.48 3.315(2) 146 no
C46 H46 O24 2_556 0.95 2.59 3.289(2) 130 no
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_4
_geom_torsion
_geom_torsion_publ_flag
C21 S1 C11 C12 . . -57.2(2) y
C21 S1 C11 C16 . . 125.30(10) y
C16 C11 C12 C13 . . 0.4(2) no
S1 C11 C12 C13 . . -177.14(13) no
C11 C12 C13 C14 . . 0.7(3) no
C12 C13 C14 O14 . . 179.52(15) no
C12 C13 C14 C15 . . -0.7(3) no
O14 C14 C15 C16 . . 179.42(15) no
C13 C14 C15 C16 . . -0.3(2) no
C14 C15 C16 C11 . . 1.5(2) no
C12 C11 C16 C15 . . -1.5(2) no
S1 C11 C16 C15 . . 176.12(13) no
C11 S1 C21 C22 . . -90.00(10) y
C11 S1 C21 C26 . . 92.60(10) y
C26 C21 C22 C23 . . 0.3(2) no
S1 C21 C22 C23 . . -177.11(12) no
C21 C22 C23 C24 . . -0.2(2) no
C22 C23 C24 O24 . . 178.90(14) no
C22 C23 C24 C25 . . -0.5(2) no
O24 C24 C25 C26 . . -178.39(14) no
C23 C24 C25 C26 . . 1.0(2) no
C24 C25 C26 C21 . . -0.9(2) no
C22 C21 C26 C25 . . 0.2(2) no
S1 C21 C26 C25 . . 177.64(12) no
C36 N31 C32 C33 . . 0.7(3) no
N31 C32 C33 C34 . . -0.1(3) no
C32 C33 C34 C35 . . -0.8(3) no
C32 C33 C34 C34 . 3_666 179.37(18) no
C33 C34 C35 C36 . . 1.1(2) no
C34 C34 C35 C36 3_666 . -179.02(18) no
C32 N31 C36 C35 . . -0.3(2) no
C34 C35 C36 N31 . . -0.6(3) no
C46 N41 C42 C43 . . 1.2(2) no
N41 C42 C43 C44 . . -0.3(3) no
C42 C43 C44 C45 . . -0.9(2) no
C42 C43 C44 C54 . . 178.44(15) no
C43 C44 C45 C46 . . 1.2(2) no
C54 C44 C45 C46 . . -178.18(16) no
C42 N41 C46 C45 . . -1.0(3) no
C44 C45 C46 N41 . . -0.2(3) no
C56 N51 C52 C53 . . -0.7(3) no
N51 C52 C53 C54 . . -0.2(3) no
C52 C53 C54 C55 . . 1.3(2) no
C52 C53 C54 C44 . . 179.94(15) no
C43 C44 C54 C55 . . 25.5(2) no
C45 C44 C54 C55 . . -155.23(16) no
C43 C44 C54 C53 . . -153.14(17) no
C45 C44 C54 C53 . . 26.2(2) no
C53 C54 C55 C56 . . -1.4(2) no
C44 C54 C55 C56 . . 179.90(14) no
C52 N51 C56 C55 . . 0.5(3) no
C54 C55 C56 N51 . . 0.5(3) no
