#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/17/2011724.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_2011724
loop_
_publ_author_name
'Näther, Christian'
'Riedel, Jens'
'Jeß, Inke'
_publ_section_title
;
 4,4'-Bipyridine dihydrate at 130K
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              111
_journal_page_last               112
_journal_paper_doi               10.1107/S0108270100014888
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C10 H8 N2 , 2H2 O'
_chemical_formula_moiety         'C10 H8 N2 , 2H2 O'
_chemical_formula_sum            'C10 H12 N2 O2'
_chemical_formula_weight         192.22
_chemical_name_common            '4,4'-Bipyridine dihydrate'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.052(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1333(7)
_cell_length_b                   7.4310(4)
_cell_length_c                   14.7171(12)
_cell_measurement_reflns_used    5270
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3
_cell_volume                     980.32(13)
_computing_cell_refinement       IPDS
_computing_data_collection       'IPDS (Stoe & Cie, 1998)'
_computing_data_reduction        IPDS
_computing_molecular_graphics    'XP in SHELXTL/PC (Siemens, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full .981
_diffrn_measured_fraction_theta_max .981
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .043
_diffrn_reflns_av_sigmaI/netI    .031
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7618
_diffrn_reflns_theta_full        25.96
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        negligible
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .06
_exptl_crystal_size_min          .05
_refine_diff_density_max         .19
_refine_diff_density_min         -.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          .073
_refine_ls_R_factor_gt           .041
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0803P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .126
_reflns_number_gt                1278
_reflns_number_total             2044
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln1112.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (26 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (26
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (32
times).

'_geom_torsion_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (40 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        980.32(12)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2011724
_cod_database_fobs_code          2011724
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
N1 .5589(4) .5588(6) -.2292(2) .0208(9) Uani d . 1 . . N
N2 .4503(4) .5629(7) .2362(2) .0212(9) Uani d . 1 . . N
N3 1.0492(4) .8127(6) .2680(2) .0204(8) Uani d . 1 . . N
N4 .9438(4) .8117(7) .7329(3) .0219(9) Uani d . 1 . . N
C1 .5186(4) .5674(7) -.0443(3) .0164(8) Uani d . 1 . . C
C2 .4061(4) .6219(7) -.1172(3) .0176(8) Uani d . 1 . . C
H2 .3129 .6619 -.1050 .021 Uiso calc R 1 . . H
C3 .4298(4) .6179(7) -.2057(3) .0191(8) Uani d . 1 . . C
H3 .3521 .6586 -.2537 .023 Uiso calc R 1 . . H
C4 .6675(4) .5084(7) -.1594(3) .0201(9) Uani d . 1 . . C
H4 .7591 .4686 -.1740 .024 Uiso calc R 1 . . H
C5 .6543(4) .5107(7) -.0663(3) .0187(9) Uani d . 1 . . C
H5 .7352 .4747 -.0191 .022 Uiso calc R 1 . . H
C6 .4958(4) .5684(7) .0523(3) .0162(8) Uani d . 1 . . C
C7 .3608(4) .5105(7) .0736(3) .0196(9) Uani d . 1 . . C
H7 .2818 .4716 .0259 .024 Uiso calc R 1 . . H
C8 .3431(4) .5106(8) .1657(3) .0205(9) Uani d . 1 . . C
H8 .2505 .4716 .1790 .025 Uiso calc R 1 . . H
C9 .5794(4) .6223(7) .2137(3) .0198(8) Uani d . 1 . . C
H9 .6556 .6645 .2622 .024 Uiso calc R 1 . . H
C10 .6066(4) .6252(7) .1256(3) .0191(8) Uani d . 1 . . C
H10 .7002 .6656 .1144 .023 Uiso calc R 1 . . H
C11 1.0061(4) .8170(7) .4517(3) .0169(9) Uani d . 1 . . C
C12 .8945(4) .8764(7) .3796(3) .0176(8) Uani d . 1 . . C
H12 .8019 .9190 .3913 .021 Uiso calc R 1 . . H
C13 .9230(4) .8714(7) .2895(3) .0201(9) Uani d . 1 . . C
H13 .8470 .9127 .2406 .024 Uiso calc R 1 . . H
C14 1.1555(5) .7566(8) .3388(3) .0216(9) Uani d . 1 . . C
H14 1.2467 .7137 .3249 .026 Uiso calc R 1 . . H
C15 1.1401(4) .7577(7) .4293(3) .0183(9) Uani d . 1 . . C
H15 1.2197 .7185 .4766 .022 Uiso calc R 1 . . H
C16 .9830(4) .8163(8) .5484(3) .0172(9) Uani d . 1 . . C
C17 .8488(4) .7628(7) .5719(3) .0192(9) Uani d . 1 . . C
H17 .7671 .7281 .5249 .023 Uiso calc R 1 . . H
C18 .8352(5) .7604(8) .6632(3) .0223(9) Uani d . 1 . . C
H18 .7437 .7202 .6777 .027 Uiso calc R 1 . . H
C19 1.0706(4) .8647(7) .7109(3) .0211(9) Uani d . 1 . . C
H19 1.1486 .9016 .7597 .025 Uiso calc R 1 . . H
C20 1.0980(4) .8703(7) .6206(3) .0180(8) Uani d . 1 . . C
H20 1.1915 .9095 .6086 .022 Uiso calc R 1 . . H
O1 .4437(3) .5899(6) .57807(17) .0294(11) Uani d . 1 . . O
H1O1 .5031 .5704 .6335 .044 Uiso d R 1 . . H
H2O1 .4769 .5434 .5293 .044 Uiso d R 1 . . H
O2 .5446(3) .4639(6) .42664(18) .0288(11) Uani d . 1 . . O
H1O2 .4984 .4994 .3699 .043 Uiso d R 1 . . H
H2O2 .5475 .3430 .4237 .043 Uiso d R 1 . . H
O3 .9399(3) .8450(6) .07543(18) .0287(10) Uani d . 1 . . O
H1O3 1.0012 .8307 .1306 .043 Uiso d R 1 . . H
H2O3 .9744 .7962 .0276 .043 Uiso d R 1 . . H
O4 1.0446(3) .7191(7) .92429(18) .0293(11) Uani d . 1 . . O
H1O4 .9930 .7494 .8680 .044 Uiso d R 1 . . H
H2O4 1.0344 .5986 .9255 .044 Uiso d 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 '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
_geom_angle_publ_flag
C4 N1 C3 116.5(4) n
C8 N2 C9 116.3(4) n
C13 N3 C14 116.6(4) n
C19 N4 C18 116.9(4) n
C2 C1 C5 117.5(4) n
C2 C1 C6 121.3(4) n
C5 C1 C6 121.1(4) n
C3 C2 C1 120.0(4) n
C2 C3 N1 123.6(4) n
N1 C4 C5 123.9(4) n
C4 C5 C1 118.3(4) n
C10 C6 C7 117.4(4) n
C10 C6 C1 122.1(4) n
C7 C6 C1 120.5(4) n
C8 C7 C6 119.3(4) n
N2 C8 C7 123.3(4) n
N2 C9 C10 124.2(4) n
C9 C10 C6 119.5(4) n
C12 C11 C15 117.7(4) n
C12 C11 C16 121.1(4) n
C15 C11 C16 121.2(4) n
C11 C12 C13 118.1(4) n
N3 C13 C12 124.2(4) n
N3 C14 C15 124.0(4) n
C14 C15 C11 119.3(4) n
C17 C16 C20 117.4(4) n
C17 C16 C11 122.2(4) n
C20 C16 C11 120.3(4) n
C18 C17 C16 119.6(4) n
N4 C18 C17 123.7(4) n
N4 C19 C20 124.5(4) n
C19 C20 C16 117.8(4) n
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
N1 C4 . 1.337(6) n
N1 C3 . 1.363(5) n
N2 C8 . 1.341(6) n
N2 C9 . 1.359(5) n
N3 C13 . 1.326(5) n
N3 C14 . 1.347(6) n
N4 C19 . 1.321(5) n
N4 C18 . 1.339(6) n
C1 C2 . 1.396(5) n
C1 C5 . 1.404(6) n
C1 C6 . 1.476(6) n
C2 C3 . 1.361(5) n
C4 C5 . 1.399(6) n
C6 C10 . 1.396(6) n
C6 C7 . 1.397(6) n
C7 C8 . 1.395(6) n
C9 C10 . 1.365(5) n
C11 C12 . 1.394(6) n
C11 C15 . 1.399(6) n
C11 C16 . 1.478(6) n
C12 C13 . 1.400(5) n
C14 C15 . 1.366(6) n
C16 C17 . 1.395(6) n
C16 C20 . 1.401(6) n
C17 C18 . 1.373(6) n
C19 C20 . 1.399(5) n
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
O1 H11O N1 1_556 .90 1.99 2.839(4) 157 yes
O1 H21O O2 . .90 1.84 2.735(4) 176 yes
O2 H12O N2 . .90 1.99 2.866(4) 164 yes
O2 H22O O1 2_646 .90 1.88 2.783(6) 178 yes
O3 H13O N3 . .90 1.99 2.829(4) 155 yes
O3 H23O O4 1_554 .90 1.85 2.748(4) 174 yes
O4 H14O N4 . .90 2.01 2.874(5) 162 yes
O4 H24O O3 2_746 .90 1.90 2.784(7) 167 yes
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
_geom_torsion_publ_flag
C5 C1 C2 C3 .4(7) n
C6 C1 C2 C3 -179.4(4) n
C1 C2 C3 N1 1.5(8) n
C4 N1 C3 C2 -2.2(7) n
C3 N1 C4 C5 1.1(8) n
N1 C4 C5 C1 .7(9) n
C2 C1 C5 C4 -1.4(8) n
C6 C1 C5 C4 178.3(4) n
C2 C1 C6 C10 -139.2(6) n
C5 C1 C6 C10 41.1(6) n
C2 C1 C6 C7 41.2(6) n
C5 C1 C6 C7 -138.6(7) n
C10 C6 C7 C8 -.5(8) n
C1 C6 C7 C8 179.1(4) n
C9 N2 C8 C7 1.8(8) n
C6 C7 C8 N2 -.4(9) n
C8 N2 C9 C10 -2.4(7) n
N2 C9 C10 C6 1.6(8) n
C7 C6 C10 C9 .0(7) n
C1 C6 C10 C9 -179.7(4) n
C15 C11 C12 C13 .6(7) n
C16 C11 C12 C13 -179.2(4) n
C14 N3 C13 C12 -.6(7) n
C11 C12 C13 N3 .4(8) n
C13 N3 C14 C15 -.2(8) n
N3 C14 C15 C11 1.2(9) n
C12 C11 C15 C14 -1.3(8) n
C16 C11 C15 C14 178.5(4) n
C12 C11 C16 C17 41.1(6) n
C15 C11 C16 C17 -138.6(7) n
C12 C11 C16 C20 -139.0(7) n
C15 C11 C16 C20 41.2(6) n
C20 C16 C17 C18 -1.6(8) n
C11 C16 C17 C18 178.3(4) n
C19 N4 C18 C17 -.9(8) n
C16 C17 C18 N4 1.8(9) n
C18 N4 C19 C20 -.1(7) n
N4 C19 C20 C16 .1(8) n
C17 C16 C20 C19 .7(7) n
C11 C16 C20 C19 -179.2(4) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2105634
