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###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
data_global
_journal_date_recd_electronic     2001-10-15
_journal_date_accepted     2001-10-18
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2002
_journal_volume     58
_journal_issue      1
_journal_page_first     o34
_journal_page_last     o35
_journal_paper_category     FO
_publ_contact_author_name     'Francesco Neve'
_publ_contact_author_address
;
Dipartimento di Chimica
Universitá della Calabria
87030 Arcavacata di Rende (CS)
Italy
;
_publ_contact_author_email     f.neve@unical.it
_publ_contact_author_fax     '0984492044'
_publ_contact_author_phone     '0984492060'
_publ_section_title
;
2,6-Diphenylpyridine-4-carboxylic acid
;
_publ_section_title_footnote
;
?
;
loop_
    _publ_author_name
    _publ_author_address
    'Crispini, Alessandra'
;
Dipartimento di Chimica
Universitá della Calabria
87030 Arcavacata di Rende (CS)
Italy
;
    'Neve, Francesco'
;
Dipartimento di Chimica
Universitá della Calabria
87030 Arcavacata di Rende (CS)
Italy
;
_publ_section_synopsis
;
?
;
data_I
_chemical_formula_moiety     'C18 H13 N O2'
_chemical_formula_sum     'C18 H13 N O2'
_chemical_formula_weight     275.29
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n '
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     16.524(4)
_cell_length_b     5.2898(9)
_cell_length_c     17.021(3)
_cell_angle_alpha     90.00
_cell_angle_beta     111.229(17)
_cell_angle_gamma     90.00
_cell_volume     1386.8(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     7.96
_cell_measurement_theta_max     12.86
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     pale_yellow
_exptl_crystal_size_max      .23
_exptl_crystal_size_mid      .20
_exptl_crystal_size_min      .17
_exptl_crystal_density_diffrn     1.32
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     576
_exptl_absorpt_coefficient_mu      .086
_exptl_absorpt_correction_type     none
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Siemens R3m/V'
_diffrn_measurement_method     'θ/2θ'
_diffrn_reflns_number     2559
_diffrn_reflns_av_R_equivalents      .069
_diffrn_reflns_theta_min     1.50
_diffrn_reflns_theta_max     25.05
_diffrn_reflns_theta_full     25.05
_diffrn_measured_fraction_theta_max      .999
_diffrn_measured_fraction_theta_full      .999
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     2
_diffrn_standards_interval_time     48
_diffrn_standards_decay_%     'no decay, variation 0.5'
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    3 2 -3
    -2 2 3
_reflns_number_total     2469
_reflns_number_gt     980
_reflns_threshold_expression     'I >2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .1272
_refine_ls_R_factor_gt      .0448
_refine_ls_wR_factor_ref      .0892
_refine_ls_goodness_of_fit_ref      .872
_refine_ls_restrained_S_all      .872
_refine_ls_number_reflns     2469
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0250P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .000
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .132
_refine_diff_density_min      -.128
_refine_ls_extinction_method     none
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'
_computing_data_collection     'XPREP (Bruker, 1997)'
_computing_cell_refinement     'XPREP (Bruker, 1997)'
_computing_data_reduction     'XPREP (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'XP (Bruker, 1997)'
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
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  .92467(13)  .1108(4)  .69830(13)  .0515(6) Uani 1 d 1 . . N
    O1 1.05832(11)  .7793(4)  .57999(10)  .0709(6) Uani 1 d 1 . . O
    H1 1.0619  .9040  .5528  .106 Uiso 1 calc 1 . R H
    O2  .91707(11)  .8373(4)  .50817(11)  .0674(6) Uani 1 d 1 . . O
    C2  .85978(16)  .2316(5)  .63842(16)  .0483(7) Uani 1 d 1 . . C
    C3  .87627(16)  .4328(5)  .59355(16)  .0518(8) Uani 1 d 1 . . C
    H3  .8307  .5145  .5523  .062 Uiso 1 calc 1 . R H
    C4  .96062(17)  .5099(5)  .61078(16)  .0481(7) Uani 1 d 1 . . C
    C5 1.02650(16)  .3905(5)  .67265(16)  .0542(8) Uani 1 d 1 . . C
    H5 1.0836  .4438  .6863  .065 Uiso 1 calc 1 . R H
    C6 1.00715(16)  .1875(5)  .71508(16)  .0513(8) Uani 1 d 1 . . C
    C7  .97728(18)  .7241(5)  .56290(17)  .0527(8) Uani 1 d 1 . . C
    C8 1.07541(17)  .0392(5)  .78092(16)  .0518(7) Uani 1 d 1 . . C
    C9 1.16336(18)  .0702(7)  .79678(18)  .0833(11) Uani 1 d 1 . . C
    H9 1.1815  .1914  .7671  .100 Uiso 1 calc 1 . R H
    C10 1.22390(19)  -.0766(7)  .8559(2)  .0853(11) Uani 1 d 1 . . C
    H10 1.2825  -.0517  .8658  .102 Uiso 1 calc 1 . R H
    C11 1.20051(19)  -.2564(6)  .90019(17)  .0743(10) Uani 1 d 1 . . C
    H11 1.2422  -.3560  .9394  .089 Uiso 1 calc 1 . R H
    C12 1.11401(19)  -.2885(7)  .88584(19)  .0910(11) Uani 1 d 1 . . C
    H12 1.0964  -.4100  .9157  .109 Uiso 1 calc 1 . R H
    C13 1.05300(18)  -.1394(6)  .8267(2)  .0764(10) Uani 1 d 1 . . C
    H13  .9946  -.1623  .8181  .092 Uiso 1 calc 1 . R H
    C14  .77008(16)  .1425(5)  .62523(16)  .0490(7) Uani 1 d 1 . . C
    C15  .75731(16)  -.0738(6)  .66479(16)  .0583(8) Uani 1 d 1 . . C
    H15  .8051  -.1684  .6974  .070 Uiso 1 calc 1 . R H
    C16  .67528(18)  -.1521(6)  .65700(17)  .0688(9) Uani 1 d 1 . . C
    H16  .6680  -.2968  .6848  .083 Uiso 1 calc 1 . R H
    C17  .60398(19)  -.0149(7)  .60776(19)  .0730(10) Uani 1 d 1 . . C
    H17  .5484  -.0671  .6022  .088 Uiso 1 calc 1 . R H
    C18  .61493(18)  .1974(7)  .56717(19)  .0743(9) Uani 1 d 1 . . C
    H18  .5668  .2902  .5341  .089 Uiso 1 calc 1 . R H
    C19  .69789(17)  .2752(6)  .57512(17)  .0639(8) Uani 1 d 1 . . C
    H19  .7048  .4181  .5464  .077 Uiso 1 calc 1 . R H
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 C2 . 1.343(3) y
    N1 C6 . 1.350(3) y
    O1 C7 . 1.297(3) y
    O1 H1 .  .8200 n
    O2 C7 . 1.243(3) y
    C2 C3 . 1.393(3) y
    C2 C14 . 1.493(3) n
    C3 C4 . 1.378(3) y
    C3 H3 .  .9300 n
    C4 C5 . 1.365(3) y
    C4 C7 . 1.478(3) y
    C5 C6 . 1.394(3) y
    C5 H5 .  .9300 n
    C6 C8 . 1.493(3) n
    C8 C13 . 1.359(3) n
    C8 C9 . 1.389(3) n
    C9 C10 . 1.374(4) n
    C9 H9 .  .9300 n
    C10 C11 . 1.354(4) n
    C10 H10 .  .9300 n
    C11 C12 . 1.371(3) n
    C11 H11 .  .9300 n
    C12 C13 . 1.384(4) n
    C12 H12 .  .9300 n
    C13 H13 .  .9300 n
    C14 C19 . 1.381(3) n
    C14 C15 . 1.382(3) n
    C15 C16 . 1.377(3) n
    C15 H15 .  .9300 n
    C16 C17 . 1.379(4) n
    C16 H16 .  .9300 n
    C17 C18 . 1.364(4) n
    C17 H17 .  .9300 n
    C18 C19 . 1.390(3) n
    C18 H18 .  .9300 n
    C19 H19 .  .9300 n
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
    C2 N1 C6 . . 119.0(2) n
    C7 O1 H1 . . 109.5 n
    N1 C2 C3 . . 121.2(2) n
    N1 C2 C14 . . 116.1(3) n
    C3 C2 C14 . . 122.6(3) n
    C4 C3 C2 . . 119.5(3) n
    C4 C3 H3 . . 120.2 n
    C2 C3 H3 . . 120.2 n
    C5 C4 C3 . . 119.3(3) n
    C5 C4 C7 . . 121.6(3) n
    C3 C4 C7 . . 119.0(3) n
    C4 C5 C6 . . 119.2(2) n
    C4 C5 H5 . . 120.4 n
    C6 C5 H5 . . 120.4 n
    N1 C6 C5 . . 121.7(2) n
    N1 C6 C8 . . 115.6(3) n
    C5 C6 C8 . . 122.8(2) n
    O2 C7 O1 . . 122.8(3) y
    O2 C7 C4 . . 121.6(2) y
    O1 C7 C4 . . 115.6(3) y
    C13 C8 C9 . . 117.0(3) n
    C13 C8 C6 . . 120.5(3) n
    C9 C8 C6 . . 122.5(3) n
    C10 C9 C8 . . 120.6(3) n
    C10 C9 H9 . . 119.7 n
    C8 C9 H9 . . 119.7 n
    C11 C10 C9 . . 121.7(3) n
    C11 C10 H10 . . 119.1 n
    C9 C10 H10 . . 119.1 n
    C10 C11 C12 . . 118.5(3) n
    C10 C11 H11 . . 120.7 n
    C12 C11 H11 . . 120.7 n
    C11 C12 C13 . . 119.8(3) n
    C11 C12 H12 . . 120.1 n
    C13 C12 H12 . . 120.1 n
    C8 C13 C12 . . 122.4(3) n
    C8 C13 H13 . . 118.8 n
    C12 C13 H13 . . 118.8 n
    C19 C14 C15 . . 118.1(3) n
    C19 C14 C2 . . 121.4(3) n
    C15 C14 C2 . . 120.4(3) n
    C16 C15 C14 . . 121.4(3) n
    C16 C15 H15 . . 119.3 n
    C14 C15 H15 . . 119.3 n
    C15 C16 C17 . . 119.6(3) n
    C15 C16 H16 . . 120.2 n
    C17 C16 H16 . . 120.2 n
    C18 C17 C16 . . 120.0(3) n
    C18 C17 H17 . . 120.0 n
    C16 C17 H17 . . 120.0 n
    C17 C18 C19 . . 120.1(3) n
    C17 C18 H18 . . 120.0 n
    C19 C18 H18 . . 120.0 n
    C14 C19 C18 . . 120.7(3) n
    C14 C19 H19 . . 119.6 n
    C18 C19 H19 . . 119.6 n
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_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 N1 C2 C3 . . . .  .2(4) n
    C6 N1 C2 C14 . . . . -178.0(2) n
    N1 C2 C3 C4 . . . .  .0(4) n
    C14 C2 C3 C4 . . . . 178.1(2) n
    C2 C3 C4 C5 . . . . -1.2(4) n
    C2 C3 C4 C7 . . . . -179.8(2) n
    C3 C4 C5 C6 . . . . 2.1(4) n
    C7 C4 C5 C6 . . . . -179.2(2) n
    C2 N1 C6 C5 . . . .  .8(4) n
    C2 N1 C6 C8 . . . . -178.5(2) n
    C4 C5 C6 N1 . . . . -2.0(4) n
    C4 C5 C6 C8 . . . . 177.3(2) n
    C5 C4 C7 O2 . . . . -178.0(3) n
    C3 C4 C7 O2 . . . .  .7(4) y
    C5 C4 C7 O1 . . . . 4.1(4) y
    C3 C4 C7 O1 . . . . -177.2(2) n
    N1 C6 C8 C13 . . . . -7.6(4) y
    C5 C6 C8 C13 . . . . 173.0(3) n
    N1 C6 C8 C9 . . . . 170.5(3) n
    C5 C6 C8 C9 . . . . -8.9(4) n
    C13 C8 C9 C10 . . . .  .5(5) n
    C6 C8 C9 C10 . . . . -177.7(3) n?
    C8 C9 C10 C11 . . . .  .5(5) n
    C9 C10 C11 C12 . . . .  -.9(5) n
    C10 C11 C12 C13 . . . .  .4(5) n
    C9 C8 C13 C12 . . . . -1.0(5) n
    C6 C8 C13 C12 . . . . 177.2(3) n
    C11 C12 C13 C8 . . . .  .6(5) n
    N1 C2 C14 C19 . . . . 170.0(2) n
    C3 C2 C14 C19 . . . . -8.2(4) n
    N1 C2 C14 C15 . . . . -8.6(3) y
    C3 C2 C14 C15 . . . . 173.3(2) n
    C19 C14 C15 C16 . . . . -2.0(4) n
    C2 C14 C15 C16 . . . . 176.6(2) n
    C14 C15 C16 C17 . . . . 1.0(4) n
    C15 C16 C17 C18 . . . .  -.1(5) n
    C16 C17 C18 C19 . . . .  .2(5) n
    C15 C14 C19 C18 . . . . 2.1(4) n
    C2 C14 C19 C18 . . . . -176.4(2) n
    C17 C18 C19 C14 . . . . -1.3(4) 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 H1 O2 3_776  .82 1.83 2.640(3) 172 y
    C11 H11 O2 4_666  .93 2.70 3.406(3) 134 y
