#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202457.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_2202457
loop_
_publ_author_name
' Lee, Ting Wai '
' Lau, Jasmine Po Kwan'
' Szeto, Lap '
_publ_section_title
;
 Diphenic acid--4,4'-bipyridine (2/1)
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o942
_journal_page_last               o944
_journal_paper_doi               10.1107/S1600536803012194
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C28 H20 O8, C10 H8 N2'
_chemical_formula_sum            'C38 H28 N2 O8'
_chemical_formula_weight         640.62
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                99.45(5)
_cell_angle_beta                 100.93(3)
_cell_angle_gamma                98.42(5)
_cell_formula_units_Z            1
_cell_length_a                   6.498(2)
_cell_length_b                   8.002(7)
_cell_length_c                   16.208(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      16.3
_cell_measurement_theta_min      13.2
_cell_volume                     802.4(8)
_computing_cell_refinement       'AFC Diffractometer Control'
_computing_data_collection
'AFC Diffractometer Control (Molecular Structure Corporation, 1992)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1992)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       AFC7R
_diffrn_measurement_method       'ω/2-θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3049
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        -0.91
_diffrn_standards_interval_count 250
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             334.00
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.306
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2830
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'calc w = 1/[(σ)²(Fo)+0.00016(Fo)²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0425
_refine_ls_wR_factor_ref         0.0538
_reflns_number_gt                1448
_reflns_number_total             2830
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6221.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 38 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1       '
_cod_original_formula_sum        'C38 H28 N2 O8 '
_cod_database_code               2202457
loop_
_symmetry_equiv_pos_as_xyz
'  +x,  +y,  +z'
'  -x,  -y,  -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
O1 1.1226(3) 0.6029(2) 0.36520(10) 0.0703(6) Uani ? ?
O2 0.8605(3) 0.4039(2) 0.28360(10) 0.0895(7) Uani ? ?
O3 0.8094(3) 0.3251(2) -0.00250(10) 0.0666(6) Uani ? ?
O4 0.8892(3) 0.5837(2) 0.08160(10) 0.0651(6) Uani ? ?
N1 0.7048(4) 0.6498(3) 0.57330(10) 0.0713(8) Uani ? ?
C1 0.9452(4) 0.5522(3) 0.30540(10) 0.0495(7) Uani ? ?
C2 0.8630(3) 0.6970(3) 0.27110(10) 0.0431(6) Uani ? ?
C3 0.9730(4) 0.8641(3) 0.30420(10) 0.0557(7) Uani ? ?
C4 0.8981(4) 1.0036(3) 0.2778(2) 0.0650(8) Uani ? ?
C5 0.7092(5) 0.9766(3) 0.2186(2) 0.0663(9) Uani ? ?
C6 0.5989(4) 0.8119(3) 0.18440(10) 0.0566(7) Uani ? ?
C7 0.6748(3) 0.6686(3) 0.20780(10) 0.0430(6) Uani ? ?
C8 0.5456(3) 0.4946(3) 0.16490(10) 0.0449(6) Uani ? ?
C9 0.3618(4) 0.4401(3) 0.19230(10) 0.0579(8) Uani ? ?
C10 0.2305(4) 0.2831(4) 0.1550(2) 0.0671(9) Uani ? ?
C11 0.2781(4) 0.1768(3) 0.0886(2) 0.0658(8) Uani ? ?
C12 0.4556(4) 0.2291(3) 0.05860(10) 0.0558(7) Uani ? ?
C13 0.5910(3) 0.3871(3) 0.09530(10) 0.0439(6) Uani ? ?
C14 0.7746(3) 0.4365(3) 0.05640(10) 0.0455(7) Uani ? ?
C15 0.5568(5) 0.7174(4) 0.6042(2) 0.0830(10) Uani ? ?
C16 0.4722(4) 0.8523(4) 0.5777(2) 0.0790(10) Uani ? ?
C17 0.5414(4) 0.9248(3) 0.51460(10) 0.0539(7) Uani ? ?
C18 0.6927(5) 0.8521(4) 0.4809(2) 0.0830(10) Uani ? ?
C19 0.7694(5) 0.7169(4) 0.5118(2) 0.0860(10) Uani ? ?
H1 1.177(5) 0.499(4) 0.388(2) 0.130(10) Uani ? ?
H2 0.973(6) 0.369(4) -0.038(2) 0.160(10) Uani ? ?
H3 1.1026 0.8829 0.3459 0.0669 Uani ? ?
H4 0.9764 1.1171 0.3005 0.0780 Uani ? ?
H5 0.6544 1.0721 0.2011 0.0795 Uani ? ?
H6 0.4678 0.7955 0.1438 0.0679 Uani ? ?
H7 0.3253 0.5124 0.2379 0.0695 Uani ? ?
H8 0.1065 0.2486 0.1755 0.0806 Uani ? ?
H9 0.1890 0.0682 0.0637 0.0789 Uani ? ?
H10 0.4872 0.1564 0.0118 0.0669 Uani ? ?
H11 0.5043 0.6699 0.6479 0.1002 Uani ? ?
H12 0.3655 0.8955 0.6032 0.0953 Uani ? ?
H13 0.7454 0.8947 0.4361 0.0995 Uani ? ?
H14 0.8749 0.6697 0.4872 0.1037 Uani ? ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.003 0.002 'International Tables'
O 0.011 0.006 'International Tables'
N 0.006 0.003 'International Tables'
H 0.000 0.000 'International Tables'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -1 4
-2 0 4
1 1 3
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
_geom_angle_publ_flag
C1 O1 H1 ? ? 111.0(10) no
C14 O3 H2 ? ? 117.0(10) no
C15 N1 C19 ? ? 115.8(2) no
O1 C1 O2 ? ? 121.9(2) no
O1 C1 C2 ? ? 113.2(2) no
O2 C1 C2 ? ? 124.9(2) no
C1 C2 C3 ? ? 119.0(2) no
C1 C2 C7 ? ? 121.5(2) no
C3 C2 C7 ? ? 119.4(2) no
C2 C3 C4 ? ? 121.4(2) no
C2 C3 H3 ? ? 119.3 no
C4 C3 H3 ? ? 119.3 no
C3 C4 C5 ? ? 119.2(2) no
C3 C4 H4 ? ? 120.4 no
C5 C4 H4 ? ? 120.4 no
C4 C5 C6 ? ? 120.2(2) no
C4 C5 H5 ? ? 119.9 no
C6 C5 H5 ? ? 119.9 no
C5 C6 C7 ? ? 121.6(2) no
C5 C6 H6 ? ? 119.2 no
C7 C6 H6 ? ? 119.2 no
C2 C7 C6 ? ? 118.0(2) no
C2 C7 C8 ? ? 124.6(2) no
C6 C7 C8 ? ? 117.4(2) no
C7 C8 C9 ? ? 117.8(2) no
C7 C8 C13 ? ? 124.4(2) no
C9 C8 C13 ? ? 117.7(2) no
C8 C9 C10 ? ? 121.6(2) no
C8 C9 H7 ? ? 119.2 no
C10 C9 H7 ? ? 119.2 no
C9 C10 C11 ? ? 120.5(2) no
C9 C10 H8 ? ? 119.7 no
C11 C10 H8 ? ? 119.8 no
C10 C11 C12 ? ? 119.3(2) no
C10 C11 H9 ? ? 120.4 no
C12 C11 H9 ? ? 120.4 no
C11 C12 C13 ? ? 121.3(2) no
C11 C12 H10 ? ? 119.3 no
C13 C12 H10 ? ? 119.3 no
C8 C13 C12 ? ? 119.6(2) no
C8 C13 C14 ? ? 122.7(2) no
C12 C13 C14 ? ? 117.7(2) no
O3 C14 O4 ? ? 122.2(2) no
O3 C14 C13 ? ? 117.5(2) no
O4 C14 C13 ? ? 120.2(2) no
N1 C15 C16 ? ? 124.3(3) no
N1 C15 H11 ? ? 117.8 no
C16 C15 H11 ? ? 117.8 no
C15 C16 C17 ? ? 120.2(3) no
C15 C16 H12 ? ? 119.9 no
C17 C16 H12 ? ? 119.9 no
C16 C17 C17 ? 2_676 122.1(3) no
C16 C17 C18 ? ? 115.6(2) no
C17 C17 C18 2_676 ? 122.3(3) no
C17 C18 C19 ? ? 120.3(2) no
C17 C18 H13 ? ? 119.8 no
C19 C18 H13 ? ? 119.8 no
N1 C19 C18 ? ? 123.8(3) no
N1 C19 H14 ? ? 118.1 no
C18 C19 H14 ? ? 118.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 ? ? 1.321(3) yes
O1 H1 ? ? 1.04(3) no
O2 C1 ? ? 1.197(3) yes
O3 C14 ? ? 1.272(2) yes
O3 H2 ? ? 1.33(4) no
O4 C14 ? ? 1.256(2) yes
N1 C15 ? ? 1.309(3) yes
N1 C19 ? ? 1.313(3) yes
C1 C2 ? ? 1.489(3) yes
C2 C3 ? ? 1.388(3) no
C2 C7 ? ? 1.402(3) no
C3 C4 ? ? 1.379(3) no
C3 H3 ? ? 0.95 no
C4 C5 ? ? 1.372(3) no
C4 H4 ? ? 0.95 no
C5 C6 ? ? 1.375(3) no
C5 H5 ? ? 0.95 no
C6 C7 ? ? 1.393(3) no
C6 H6 ? ? 0.95 no
C7 C8 ? ? 1.498(3) yes
C8 C9 ? ? 1.389(3) no
C8 C13 ? ? 1.408(3) no
C9 C10 ? ? 1.383(3) no
C9 H7 ? ? 0.95 no
C10 C11 ? ? 1.370(4) no
C10 H8 ? ? 0.95 no
C11 C12 ? ? 1.372(3) no
C11 H9 ? ? 0.95 no
C12 C13 ? ? 1.399(3) no
C12 H10 ? ? 0.95 no
C13 C14 ? ? 1.486(3) yes
C15 C16 ? ? 1.375(4) yes
C15 H11 ? ? 0.95 no
C16 C17 ? ? 1.370(3) yes
C16 H12 ? ? 0.95 no
C17 C17 ? 2_676 1.497(4) yes
C17 C18 ? ? 1.368(3) yes
C18 C19 ? ? 1.382(4) yes
C18 H13 ? ? 0.95 no
C19 H14 ? ? 0.95 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
O3 H2 O4 2_765 1.33(4) 1.29(4) 2.618(3) 171(3)
O1 H1 N1 2_766 1.04(3) 1.65(3) 2.691(4) 172(3)
C4 H4 O2 1_565 0.95 2.56 3.235(4) 128
C6 H6 O3 2_665 0.95 2.57 3.472(4) 158
C3 H3 O1 . 0.95 2.33 2.683(4) 101
C12 H10 O3 . 0.95 2.39 2.730(4) 100
