#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/03/2220389.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_2220389
loop_
_publ_author_name
'Qin, Jian-Hua'
'Hao, Er-Jun'
'Wang, Jian-Ge'
_publ_section_title
;
 1,3-Di-4-pyridylpropane--2-hydroxybenzene-1,4-dicarboxylic acid (1/2)
;
_journal_coeditor_code           WW2129
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2398
_journal_paper_doi               10.1107/S1600536808037835
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H14 N2, 2C8 H6 O5'
_chemical_formula_moiety         'C13 H14 N2, 2(C8 H6 O5)'
_chemical_formula_sum            'C29 H26 N2 O10'
_chemical_formula_weight         562.52
_chemical_name_systematic
;
1,3-Di-4-pyridylpropane--2-hydroxybenzene-1,4-dicarboxylic acid (1/2)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 96.542(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.939(11)
_cell_length_b                   4.781(2)
_cell_length_c                   24.163(11)
_cell_measurement_reflns_used    1102
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      23.27
_cell_measurement_theta_min      3.39
_cell_volume                     2633(2)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω & φ 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  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9178
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0564
_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)+(0.0772P)²+1.3530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1728
_reflns_number_gt                1335
_reflns_number_total             2444
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww2129.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'C 2/c'
_cod_database_code               2220389
_cod_database_fobs_code          2220389
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
O O1 0.38415(11) 1.0471(6) 0.32590(9) 0.0857(9) Uani d . 1
H H1 0.3557 0.9516 0.3141 0.129 Uiso calc R 1
O O2 0.24082(9) 0.8169(5) 0.40221(9) 0.0642(7) Uani d . 1
H H2 0.2203 0.6976 0.3852 0.096 Uiso calc R 1
O O3 0.29118(9) 0.7716(5) 0.32941(9) 0.0695(7) Uani d . 1
O O4 0.43663(9) 1.8252(5) 0.51792(9) 0.0666(7) Uani d . 1
H H4 0.4624 1.9400 0.5274 0.100 Uiso calc R 1
O O5 0.48854(9) 1.7794(5) 0.44642(10) 0.0679(7) Uani d . 1
N N1 0.17662(11) 0.4242(5) 0.35544(11) 0.0516(7) Uani d . 1
C C1 0.32537(12) 1.0947(6) 0.40090(12) 0.0467(7) Uani d . 1
C C2 0.37382(13) 1.1721(6) 0.37430(13) 0.0539(8) Uani d . 1
C C3 0.41262(13) 1.3722(6) 0.39812(13) 0.0568(8) Uani d . 1
H H3 0.4451 1.4215 0.3805 0.068 Uiso calc R 1
C C4 0.40338(12) 1.4989(6) 0.44770(12) 0.0470(7) Uani d . 1
C C5 0.35515(13) 1.4263(6) 0.47459(13) 0.0535(8) Uani d . 1
H H5 0.3486 1.5125 0.5078 0.064 Uiso calc R 1
C C6 0.31687(13) 1.2222(6) 0.45088(13) 0.0551(8) Uani d . 1
H H6 0.2849 1.1702 0.4690 0.066 Uiso calc R 1
C C7 0.28337(13) 0.8782(6) 0.37506(14) 0.0527(8) Uani d . 1
C C8 0.44604(13) 1.7142(6) 0.47143(13) 0.0493(8) Uani d . 1
C C9 0.18299(12) 0.3070(7) 0.30666(13) 0.0534(8) Uani d . 1
H H9 0.2147 0.3584 0.2881 0.064 Uiso calc R 1
C C10 0.14366(12) 0.1103(6) 0.28276(12) 0.0516(8) Uani d . 1
H H10 0.1493 0.0298 0.2488 0.062 Uiso calc R 1
C C11 0.09577(12) 0.0334(6) 0.30954(12) 0.0449(7) Uani d . 1
C C12 0.09152(13) 0.1551(7) 0.36110(13) 0.0570(8) Uani d . 1
H H12 0.0609 0.1056 0.3813 0.068 Uiso calc R 1
C C13 0.13223(14) 0.3479(7) 0.38230(13) 0.0575(8) Uani d . 1
H H13 0.1285 0.4277 0.4168 0.069 Uiso calc R 1
C C14 0.04828(11) -0.1557(6) 0.28235(12) 0.0499(8) Uani d . 1
H H14A 0.0318 -0.2651 0.3106 0.060 Uiso calc R 1
H H14B 0.0648 -0.2837 0.2572 0.060 Uiso calc R 1
C C15 0.0000 0.0194(8) 0.2500 0.0498(11) Uani d S 1
H H15A 0.0176 0.1391 0.2241 0.060 Uiso calc PR 0.50
H H15B -0.0176 0.1391 0.2759 0.060 Uiso calc PR 0.50
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 O1 H1 . . 109.5
C7 O2 H2 . . 109.5
C8 O4 H4 . . 109.5
C13 N1 C9 . . 119.3(3)
C6 C1 C2 . . 118.9(3)
C6 C1 C7 . . 121.2(3)
C2 C1 C7 . . 119.9(3)
O1 C2 C3 . . 119.6(3)
O1 C2 C1 . . 120.4(3)
C3 C2 C1 . . 119.9(3)
C4 C3 C2 . . 120.6(3)
C4 C3 H3 . . 119.7
C2 C3 H3 . . 119.7
C3 C4 C5 . . 120.4(3)
C3 C4 C8 . . 118.6(3)
C5 C4 C8 . . 121.0(3)
C4 C5 C6 . . 118.8(3)
C4 C5 H5 . . 120.6
C6 C5 H5 . . 120.6
C1 C6 C5 . . 121.5(3)
C1 C6 H6 . . 119.3
C5 C6 H6 . . 119.3
O3 C7 O2 . . 124.0(3)
O3 C7 C1 . . 120.0(3)
O2 C7 C1 . . 116.0(3)
O5 C8 O4 . . 122.8(3)
O5 C8 C4 . . 120.2(3)
O4 C8 C4 . . 117.0(3)
N1 C9 C10 . . 121.7(3)
N1 C9 H9 . . 119.2
C10 C9 H9 . . 119.2
C9 C10 C11 . . 120.0(3)
C9 C10 H10 . . 120.0
C11 C10 H10 . . 120.0
C10 C11 C12 . . 116.6(3)
C10 C11 C14 . . 121.8(3)
C12 C11 C14 . . 121.4(3)
C13 C12 C11 . . 120.2(3)
C13 C12 H12 . . 119.9
C11 C12 H12 . . 119.9
N1 C13 C12 . . 122.3(3)
N1 C13 H13 . . 118.9
C12 C13 H13 . . 118.9
C11 C14 C15 . . 109.9(2)
C11 C14 H14A . . 109.7
C15 C14 H14A . . 109.7
C11 C14 H14B . . 109.7
C15 C14 H14B . . 109.7
H14A C14 H14B . . 108.2
C14 C15 C14 . 2 113.7(3)
C14 C15 H15A . . 108.8
C14 C15 H15A 2 . 108.8
C14 C15 H15B . . 108.8
C14 C15 H15B 2 . 108.8
H15A C15 H15B . . 107.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.358(3)
O1 H1 . 0.8200
O2 C7 . 1.271(3)
O2 H2 . 0.8200
O3 C7 . 1.246(4)
O4 C8 . 1.283(3)
O4 H4 . 0.8200
O5 C8 . 1.244(3)
N1 C13 . 1.320(4)
N1 C9 . 1.328(4)
C1 C6 . 1.386(4)
C1 C2 . 1.396(4)
C1 C7 . 1.501(4)
C2 C3 . 1.386(4)
C3 C4 . 1.380(4)
C3 H3 . 0.9300
C4 C5 . 1.389(4)
C4 C8 . 1.489(4)
C5 C6 . 1.391(4)
C5 H5 . 0.9300
C6 H6 . 0.9300
C9 C10 . 1.383(4)
C9 H9 . 0.9300
C10 C11 . 1.387(4)
C10 H10 . 0.9300
C11 C12 . 1.389(4)
C11 C14 . 1.507(4)
C12 C13 . 1.369(4)
C12 H12 . 0.9300
C13 H13 . 0.9300
C14 C15 . 1.530(3)
C14 H14A . 0.9700
C14 H14B . 0.9700
C15 C14 2 1.530(3)
C15 H15A . 0.9700
C15 H15B . 0.9700
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
O4 H4 O5 5_696 0.82 1.82 2.631(3) 171.6
O2 H2 N1 . 0.82 1.75 2.568(3) 174.1
O1 H1 O3 . 0.82 1.79 2.516(3) 147.3
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_site_symmetry_4
_geom_torsion
C6 C1 C2 O1 . 178.6(3)
C7 C1 C2 O1 . -1.8(4)
C6 C1 C2 C3 . 0.4(4)
C7 C1 C2 C3 . 180.0(3)
O1 C2 C3 C4 . -179.1(3)
C1 C2 C3 C4 . -0.8(5)
C2 C3 C4 C5 . 0.3(5)
C2 C3 C4 C8 . -179.5(3)
C3 C4 C5 C6 . 0.6(4)
C8 C4 C5 C6 . -179.5(3)
C2 C1 C6 C5 . 0.6(5)
C7 C1 C6 C5 . -179.0(3)
C4 C5 C6 C1 . -1.1(4)
C6 C1 C7 O3 . 178.2(3)
C2 C1 C7 O3 . -1.4(4)
C6 C1 C7 O2 . -1.3(4)
C2 C1 C7 O2 . 179.2(3)
C3 C4 C8 O5 . 0.9(4)
C5 C4 C8 O5 . -179.0(3)
C3 C4 C8 O4 . -179.1(3)
C5 C4 C8 O4 . 1.0(4)
C13 N1 C9 C10 . 1.2(4)
N1 C9 C10 C11 . 0.7(4)
C9 C10 C11 C12 . -2.3(4)
C9 C10 C11 C14 . 173.2(3)
C10 C11 C12 C13 . 2.2(4)
C14 C11 C12 C13 . -173.4(3)
C9 N1 C13 C12 . -1.4(5)
C11 C12 C13 N1 . -0.3(5)
C10 C11 C14 C15 . -90.2(3)
C12 C11 C14 C15 . 85.1(3)
C11 C14 C15 C14 2 176.1(3)
