#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/70/2217009.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_2217009
loop_
_publ_author_name
'Ling  Ye'
_publ_section_title
;
 4,4'-Bipyridine acetic acid disolvate
;
_journal_coeditor_code           DN2279
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o46
_journal_page_last               o46
_journal_paper_doi               10.1107/S1600536807062319
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H8 N2, 2C2 H4 O2'
_chemical_formula_moiety         'C10 H8 N2, 2(C2 H4 O2)'
_chemical_formula_sum            'C14 H16 N2 O4'
_chemical_formula_weight         276.29
_chemical_name_systematic
;
4,4-Bipyridine acetic acid disolvate
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.46(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.893(2)
_cell_length_b                   8.181(5)
_cell_length_c                   22.563(15)
_cell_measurement_reflns_used    4188
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.09
_cell_volume                     710.8(7)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω 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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6467
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_correction_T_min  0.9856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1595
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0545P)²+0.0575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                995
_reflns_number_total             1595
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2279.cif
_cod_data_source_block           I
_cod_original_cell_volume        710.7(7)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2217009
_cod_database_fobs_code          2217009
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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
C C13 -0.0181(13) -0.0149(6) 0.6249(2) 0.0728(12) Uani d . 1
H H13A 0.1830 -0.0660 0.6470 0.109 Uiso calc R 1
H H13B -0.1649 -0.0968 0.6039 0.109 Uiso calc R 1
H H13C -0.1437 0.0423 0.6521 0.109 Uiso calc R 1
C C14 0.0919(10) 0.1019(5) 0.5814(2) 0.0568(10) Uani d . 1
C C1 0.4437(12) 0.3978(5) 0.47047(19) 0.0697(11) Uani d . 1
H H1 0.4572 0.2861 0.4636 0.084 Uiso calc R 1
C C2 0.4896(13) 0.5031(5) 0.4247(2) 0.0640(10) Uani d . 1
H H2 0.5306 0.4622 0.3879 0.077 Uiso calc R 1
C C3 0.4742(9) 0.6695(4) 0.43371(16) 0.0488(9) Uani d . 1
C C4 0.4131(11) 0.7207(5) 0.48979(19) 0.0613(11) Uani d . 1
H H4 0.4020 0.8316 0.4984 0.074 Uiso calc R 1
C C5 0.3695(12) 0.6071(5) 0.5321(2) 0.0690(12) Uani d . 1
H H5 0.3285 0.6441 0.5694 0.083 Uiso calc R 1
C C6 0.5176(9) 0.7891(4) 0.38616(17) 0.0483(9) Uani d . 1
C C7 0.4150(11) 0.7538(5) 0.32659(19) 0.0599(11) Uani d . 1
H H7 0.3218 0.6520 0.3152 0.072 Uiso calc R 1
C C8 0.4513(11) 0.8706(5) 0.2839(2) 0.0654(11) Uani d . 1
H H8 0.3770 0.8449 0.2440 0.078 Uiso calc R 1
C C9 0.6937(12) 1.0494(5) 0.35465(19) 0.0649(11) Uani d . 1
H H9 0.7942 1.1507 0.3646 0.078 Uiso calc R 1
C C10 0.6649(11) 0.9422(5) 0.39995(18) 0.0599(10) Uani d . 1
H H10 0.7426 0.9709 0.4395 0.072 Uiso calc R 1
N N1 0.3818(10) 0.4468(4) 0.52352(16) 0.0655(9) Uani d . 1
O O1 0.9176(9) 1.3967(4) 0.29266(15) 0.0859(11) Uani d . 1
O O3 0.0627(10) 0.0786(4) 0.52832(15) 0.0938(11) Uani d . 1
C C11 0.8647(13) 1.5081(6) 0.1948(2) 0.0764(14) Uani d . 1
H H11A 1.0155 1.5926 0.2131 0.115 Uiso calc R 1
H H11B 0.6438 1.5545 0.1789 0.115 Uiso calc R 1
H H11C 0.9664 1.4585 0.1630 0.115 Uiso calc R 1
C C12 0.8156(11) 1.3817(4) 0.2405(2) 0.0565(10) Uani d . 1
N N2 0.5861(9) 1.0176(4) 0.29663(16) 0.0631(9) Uani d . 1
O O2 0.6441(8) 1.2545(3) 0.21698(13) 0.0698(8) Uani d . 1
H H2A 0.6294 1.1864 0.2432 0.105 Uiso calc R 1
O O4 0.2338(8) 0.2354(3) 0.60567(13) 0.0711(9) Uani d . 1
H H4A 0.2902 0.2947 0.5794 0.107 Uiso calc R 1
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C14 C13 H13A 109.5
C14 C13 H13B 109.5
H13A C13 H13B 109.5
C14 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O3 C14 O4 121.5(4)
O3 C14 C13 124.4(4)
O4 C14 C13 114.0(4)
N1 C1 C2 123.6(4)
N1 C1 H1 118.2
C2 C1 H1 118.2
C1 C2 C3 119.5(4)
C1 C2 H2 120.2
C3 C2 H2 120.2
C2 C3 C4 116.8(4)
C2 C3 C6 122.2(3)
C4 C3 C6 121.0(3)
C5 C4 C3 119.4(4)
C5 C4 H4 120.3
C3 C4 H4 120.3
N1 C5 C4 124.1(4)
N1 C5 H5 117.9
C4 C5 H5 117.9
C7 C6 C10 117.3(3)
C7 C6 C3 121.4(3)
C10 C6 C3 121.3(3)
C6 C7 C8 119.5(4)
C6 C7 H7 120.3
C8 C7 H7 120.3
N2 C8 C7 123.8(4)
N2 C8 H8 118.1
C7 C8 H8 118.1
N2 C9 C10 124.0(4)
N2 C9 H9 118.0
C10 C9 H9 118.0
C9 C10 C6 119.2(4)
C9 C10 H10 120.4
C6 C10 H10 120.4
C1 N1 C5 116.6(4)
C12 C11 H11A 109.5
C12 C11 H11B 109.5
H11A C11 H11B 109.5
C12 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O1 C12 O2 124.1(4)
O1 C12 C11 123.6(4)
O2 C12 C11 112.3(4)
C8 N2 C9 116.3(4)
C12 O2 H2A 109.5
C14 O4 H4A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C13 C14 1.478(6)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 O3 1.201(5)
C14 O4 1.307(5)
C1 N1 1.317(6)
C1 C2 1.377(6)
C1 H1 0.9300
C2 C3 1.380(5)
C2 H2 0.9300
C3 C4 1.386(6)
C3 C6 1.480(5)
C4 C5 1.361(6)
C4 H4 0.9300
C5 N1 1.328(5)
C5 H5 0.9300
C6 C7 1.375(5)
C6 C10 1.393(5)
C7 C8 1.378(6)
C7 H7 0.9300
C8 N2 1.326(5)
C8 H8 0.9300
C9 N2 1.340(5)
C9 C10 1.364(6)
C9 H9 0.9300
C10 H10 0.9300
O1 C12 1.191(5)
C11 C12 1.493(6)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 O2 1.306(4)
O2 H2A 0.8200
O4 H4A 0.8200
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
O2 H2A N2 . 0.82 1.86 2.675(5) 174.5
O4 H4A N1 . 0.82 1.84 2.659(5) 173.1
C7 H7 O1 1_445 0.93 2.62 3.526(5) 165.2
C10 H10 O3 1_665 0.93 2.37 3.273(5) 164.3
C4 H4 O3 1_565 0.93 2.56 3.397(6) 150.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119679
