#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/53/2015371.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_2015371
loop_
_publ_author_name
'Li, Chen-Guang'
'Robinson, Paul D.'
'Dyer, Daniel J.'
_publ_section_title
;
 Hydrogen-bonded 1:1 adduct of
 1,1'-(p-phenylene)dipyridin-4(1H)-one with terephthalic
 acid
;
_journal_coeditor_code           GZ3009
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o336
_journal_page_last               o338
_journal_paper_doi               10.1107/S0108270106015174
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H12 N2 O2, C8 H6 O4'
_chemical_formula_moiety         'C16 H12 N2 O2, C8 H6 O4'
_chemical_formula_sum            'C24 H18 N2 O6'
_chemical_formula_weight         430.40
_chemical_name_systematic
;
1-[4-(4-oxo-1,4-dihydro-1-pyridyl)phenyl]pyridin-4(1H)-one--terephthalic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.1480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.0931(2)
_cell_length_b                   10.2759(3)
_cell_length_c                   15.2973(5)
_cell_measurement_reflns_used    7275
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.4
_cell_measurement_theta_min      2.7
_cell_volume                     957.12(5)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection
;
APEXII (Bruker, 2005)
;
_computing_data_reduction
;
SAINT and SADABS (Bruker, 2005)
;
_computing_molecular_graphics
;
PLATON (Spek, 2003) and MERCURY (Bruno et al.,  2002)
;
_computing_publication_material
;
SHELXL97 and PLATON
;
_computing_structure_refinement
;
LS in TEXSAN (Molecular Structure Corporation, 1997) and
SHELXL97 (Sheldrick, 1997)
;
_computing_structure_solution    'SIR92 (Burla et al.,  1989)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full .997
_diffrn_measured_fraction_theta_max .997
_diffrn_measurement_device_type
;
Bruker Kappa-APEX-II CCD
;
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_sigmaI/netI    0.022
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17765
_diffrn_reflns_theta_full        33.38
_diffrn_reflns_theta_max         33.4
_diffrn_reflns_theta_min         2.4
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  .976
_exptl_absorpt_correction_T_min  .916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         .54
_refine_diff_density_min         -.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0683P)²+0.2721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.116
_refine_ls_wR_factor_ref         0.121
_reflns_number_gt                3183
_reflns_number_total             3717
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gz3009.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2015371
_cod_database_fobs_code          2015371
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'1/2+x, 1/2-y, 1/2+z'
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 0.20291(12) 0.22919(7) 0.22447(5) 0.01998(15) Uani d . 1
N N1 0.67339(12) 0.39370(7) 0.38658(5) 0.01201(14) Uani d . 1
C C1 0.34842(14) 0.28124(8) 0.27498(5) 0.01340(16) Uani d . 1
C C2 0.33312(14) 0.41207(8) 0.30631(6) 0.01402(16) Uani d . 1
H H2A 0.2121 0.4625 0.2893 0.017 Uiso calc R 1
C C3 0.49242(14) 0.46418(8) 0.36056(5) 0.01330(15) Uani d . 1
H H3 0.4777 0.5493 0.3802 0.016 Uiso calc R 1
C C4 0.69494(14) 0.26881(8) 0.35811(6) 0.01348(15) Uani d . 1
H H4 0.8184 0.2213 0.3761 0.016 Uiso calc R 1
C C5 0.54117(15) 0.21185(8) 0.30420(5) 0.01373(16) Uani d . 1
H H5 0.5614 0.1265 0.2860 0.016 Uiso calc R 1
C C6 0.83898(13) 0.44853(8) 0.44487(5) 0.01193(15) Uani d . 1
C C7 0.92017(14) 0.57214(8) 0.42841(5) 0.01297(15) Uani d . 1
H H7 0.8656 0.6196 0.3806 0.016 Uiso calc R 1
C C8 0.91669(14) 0.37565(8) 0.51623(5) 0.01330(15) Uani d . 1
H H8 0.8603 0.2932 0.5267 0.016 Uiso calc R 1
O O2 -0.10567(12) 0.36938(7) 0.16290(4) 0.01857(15) Uani d . 1
H H2 -0.0016 0.3246 0.1803 0.028 Uiso calc R 1
O O3 -0.02102(12) 0.28640(8) 0.03302(5) 0.02296(16) Uani d . 1
C C9 -0.32276(14) 0.43267(8) 0.03862(5) 0.01234(15) Uani d . 1
C C10 -0.48400(14) 0.48530(8) 0.09047(5) 0.01413(15) Uani d . 1
H H10 -0.4734 0.4755 0.1509 0.017 Uiso calc R 1
C C11 -0.33941(14) 0.44754(8) -0.05194(5) 0.01441(16) Uani d . 1
H H11 -0.2322 0.4125 -0.0867 0.017 Uiso calc R 1
C C12 -0.13364(14) 0.35616(8) 0.07740(6) 0.01425(16) Uani d . 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 0.0016 '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
C4 N1 C3 . 119.50(7)
C4 N1 C6 . 119.59(7)
C3 N1 C6 . 120.89(7)
O1 C1 C5 . 121.69(8)
O1 C1 C2 . 123.07(8)
C5 C1 C2 . 115.23(7)
C3 C2 C1 . 121.27(8)
C3 C2 H2A . 119.4
C1 C2 H2A . 119.4
C2 C3 N1 . 121.19(7)
C2 C3 H3 . 119.4
N1 C3 H3 . 119.4
C5 C4 N1 . 121.83(8)
C5 C4 H4 . 119.1
N1 C4 H4 . 119.1
C4 C5 C1 . 120.97(8)
C4 C5 H5 . 119.5
C1 C5 H5 . 119.5
C7 C6 C8 . 121.40(7)
C7 C6 N1 . 119.51(7)
C8 C6 N1 . 119.08(7)
C8 C7 C6 3_766 119.60(7)
C8 C7 H7 3_766 120.2
C6 C7 H7 . 120.2
C7 C8 C6 3_766 119.00(8)
C7 C8 H8 3_766 120.5
C6 C8 H8 . 120.5
C11 C9 C10 . 119.75(8)
C11 C9 C12 . 118.50(8)
C10 C9 C12 . 121.72(7)
C11 C10 C9 3_465 120.11(8)
C11 C10 H10 3_465 119.9
C9 C10 H10 . 119.9
C10 C11 C9 3_465 120.13(8)
C10 C11 H11 3_465 119.9
C9 C11 H11 . 119.9
O3 C12 O2 . 123.99(8)
O3 C12 C9 . 121.97(8)
O2 C12 C9 . 114.02(8)
C12 O2 H2 . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.2719(10)
N1 C4 . 1.3631(11)
N1 C3 . 1.3660(10)
N1 C6 . 1.4364(10)
C1 C5 . 1.4312(12)
C1 C2 . 1.4315(12)
C2 C3 . 1.3627(11)
C2 H2A . 0.9300
C3 H3 . 0.9300
C4 C5 . 1.3575(11)
C4 H4 . 0.9300
C5 H5 . 0.9300
C6 C7 . 1.3895(11)
C6 C8 . 1.3921(11)
C7 C8 3_766 1.3893(11)
C7 H7 . 0.9300
C8 H8 . 0.9300
O2 C12 . 1.3196(10)
O2 H2 . 0.8200
O3 C12 . 1.2168(11)
C9 C11 . 1.3936(11)
C9 C10 . 1.3947(12)
C9 C12 . 1.4989(12)
C10 C11 3_465 1.3906(12)
C10 H10 . 0.9300
C11 H11 . 0.9300
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
O2 H2 O1 . 0.82 1.71 2.5228(10) 175 yes
C8 H8 O3 4_555 0.93 2.47 3.1628(11) 132 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_site_symmetry_4
_geom_torsion
O1 C1 C2 C3 . 179.84(8)
C5 C1 C2 C3 . -0.43(13)
C1 C2 C3 N1 . 0.43(13)
C4 N1 C3 C2 . -0.25(13)
C6 N1 C3 C2 . -179.00(8)
C3 N1 C4 C5 . 0.09(13)
C6 N1 C4 C5 . 178.86(8)
N1 C4 C5 C1 . -0.11(14)
O1 C1 C5 C4 . 180.00(8)
C2 C1 C5 C4 . 0.27(13)
C4 N1 C6 C7 . 133.43(9)
C3 N1 C6 C7 . -47.82(12)
C4 N1 C6 C8 . -45.77(12)
C3 N1 C6 C8 . 132.99(9)
C8 C6 C7 C8 3_766 0.40(14)
N1 C6 C7 C8 3_766 -178.78(8)
C7 C6 C8 C7 3_766 -0.40(14)
N1 C6 C8 C7 3_766 178.78(8)
C11 C9 C10 C11 3_465 -0.06(14)
C12 C9 C10 C11 3_465 -178.10(8)
C10 C9 C11 C10 3_465 0.06(14)
C12 C9 C11 C10 3_465 178.16(8)
C11 C9 C12 O3 . -14.71(13)
C10 C9 C12 O3 . 163.35(9)
C11 C9 C12 O2 . 166.82(8)
C10 C9 C12 O2 . -15.11(12)
