##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-08-26
_journal_date_accepted     2009-10-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     11
_journal_page_first     o2739
_journal_page_last     o2739
_journal_paper_category     QO
_journal_coeditor_code     LX2115
_publ_contact_author_name     'Dr Liu, Hai-Xing '
_publ_contact_author_address
;
Microscale Science Institute,
Department of Chemistry and Chemical Engineering,
Weifang University, Weifang 261061,
People's Republic of China
;
_publ_contact_author_email     wj-crystal@163.com
_publ_contact_author_fax     '86-536-8785802'
_publ_contact_author_phone     '86-536-8785802'
_publ_section_title
;
3-Anilino-1,3-di-2-pyridylpropan-1-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Liu, Hai-Xing'
;
Microscale Science Institute,
Department of Chemistry and Chemical Engineering,
Weifang University, Weifang 261061,
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Anilino-1,3-di-2-pyridylpropan-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H17 N3 O'
_chemical_formula_sum     'C19 H17 N3 O'
_chemical_formula_iupac     'C19 H17 N3 O'
_chemical_formula_weight     303.36
_chemical_melting_point     400
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     p_2ac_2ab
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     9.316(2)
_cell_length_b     10.275(2)
_cell_length_c     16.652(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1594.0(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1025
_cell_measurement_theta_min     2.33
_cell_measurement_theta_max     27.03
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.264
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     0.080
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick (2000)'
_exptl_absorpt_correction_T_min     0.9496
_exptl_absorpt_correction_T_max     0.9755
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     10.0
_diffrn_reflns_number     7562
_diffrn_reflns_av_R_equivalents     0.0768
_diffrn_reflns_av_sigmaI/netI     0.1078
_diffrn_reflns_theta_min     2.33
_diffrn_reflns_theta_max     27.03
_diffrn_reflns_theta_full     27.03
_diffrn_measured_fraction_theta_max     0.980
_diffrn_measured_fraction_theta_full     0.980
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     .
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     .
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1961
_reflns_number_gt     1040
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1202
_refine_ls_R_factor_gt     0.0478
_refine_ls_wR_factor_gt     0.0963
_refine_ls_wR_factor_ref     0.1183
_refine_ls_goodness_of_fit_ref     0.999
_refine_ls_restrained_S_all     0.999
_refine_ls_number_reflns     1961
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0005P)²+0.0531P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.152
_refine_diff_density_min     -0.133
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.5253(4) 0.4411(3) 0.5808(2) 0.0934(11) Uani d . 1 . .
    N N1 0.6804(4) 0.1340(3) 0.5653(2) 0.0659(9) Uani d . 1 . .
    N N2 0.6078(3) 0.4744(3) 0.8480(2) 0.0551(8) Uani d . 1 . .
    N N3 0.3789(3) 0.2540(3) 0.7351(2) 0.0628(9) Uani d . 1 . .
    H H3N 0.3971 0.1851 0.7076 0.075 Uiso calc R 1 . .
    C C1 0.7052(5) 0.0421(5) 0.5109(3) 0.0828(14) Uani d . 1 . .
    H H1 0.7626 -0.0277 0.5260 0.099 Uiso calc R 1 . .
    C C2 0.6530(5) 0.0426(5) 0.4350(3) 0.0841(14) Uani d . 1 . .
    H H2 0.6734 -0.0252 0.3997 0.101 Uiso calc R 1 . .
    C C3 0.5700(5) 0.1446(5) 0.4115(3) 0.0754(13) Uani d . 1 . .
    H H3 0.5324 0.1480 0.3598 0.090 Uiso calc R 1 . .
    C C4 0.5428(5) 0.2424(4) 0.4655(3) 0.0693(12) Uani d . 1 . .
    H H4 0.4868 0.3135 0.4508 0.083 Uiso calc R 1 . .
    C C5 0.5998(4) 0.2338(3) 0.5418(2) 0.0531(10) Uani d . 1 . .
    C C6 0.5753(4) 0.3385(4) 0.6019(3) 0.0612(11) Uani d . 1 . .
    C C7 0.6147(4) 0.3152(4) 0.6885(2) 0.0614(11) Uani d . 1 . .
    H H7A 0.6977 0.3677 0.7021 0.074 Uiso calc R 1 . .
    H H7B 0.6405 0.2245 0.6956 0.074 Uiso calc R 1 . .
    C C8 0.4910(4) 0.3490(3) 0.7454(2) 0.0512(10) Uani d . 1 . .
    H H8 0.4527 0.4340 0.7293 0.061 Uiso calc R 1 . .
    C C9 0.5452(4) 0.3607(3) 0.8309(2) 0.0493(9) Uani d . 1 . .
    C C10 0.5356(4) 0.2627(4) 0.8858(3) 0.0660(11) Uani d . 1 . .
    H H10 0.4912 0.1846 0.8726 0.079 Uiso calc R 1 . .
    C C11 0.5924(5) 0.2811(5) 0.9609(3) 0.0828(14) Uani d . 1 . .
    H H11A 0.5857 0.2156 0.9992 0.099 Uiso calc R 1 . .
    C C12 0.6590(5) 0.3961(6) 0.9794(3) 0.0842(15) Uani d . 1 . .
    H H12 0.7000 0.4101 1.0296 0.101 Uiso calc R 1 . .
    C C13 0.6627(4) 0.4886(4) 0.9215(3) 0.0701(13) Uani d . 1 . .
    H H13 0.7065 0.5674 0.9339 0.084 Uiso calc R 1 . .
    C C14 0.2431(4) 0.2689(3) 0.7675(2) 0.0504(9) Uani d . 1 . .
    C C15 0.1444(4) 0.1682(3) 0.7591(2) 0.0552(10) Uani d . 1 . .
    H H15 0.1720 0.0907 0.7348 0.066 Uiso calc R 1 . .
    C C16 0.0075(5) 0.1827(4) 0.7863(3) 0.0652(11) Uani d . 1 . .
    H H16 -0.0574 0.1149 0.7794 0.078 Uiso calc R 1 . .
    C C17 -0.0373(4) 0.2942(4) 0.8235(3) 0.0654(11) Uani d . 1 . .
    H H17 -0.1312 0.3027 0.8417 0.078 Uiso calc R 1 . .
    C C18 0.0597(4) 0.3928(4) 0.8330(3) 0.0611(11) Uani d . 1 . .
    H H18 0.0312 0.4690 0.8586 0.073 Uiso calc R 1 . .
    C C19 0.2000(4) 0.3816(3) 0.8054(2) 0.0545(10) Uani d . 1 . .
    H H19 0.2644 0.4498 0.8124 0.065 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    O1 C6 . 1.205(4) ?
    N1 C5 . 1.329(4) ?
    N1 C1 . 1.330(5) ?
    N2 C13 . 1.335(5) ?
    N2 C9 . 1.336(4) ?
    N3 C14 . 1.384(4) ?
    N3 C8 . 1.440(4) ?
    N3 H3N . 0.8600 ?
    C1 C2 . 1.354(7) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.359(6) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.372(6) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.380(6) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.487(5) ?
    C6 C7 . 1.506(6) ?
    C7 C8 . 1.531(5) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.516(5) ?
    C8 H8 . 0.9800 ?
    C9 C10 . 1.363(5) ?
    C10 C11 . 1.370(7) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.370(6) ?
    C11 H11A . 0.9300 ?
    C12 C13 . 1.354(6) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 C19 . 1.379(5) ?
    C14 C15 . 1.390(5) ?
    C15 C16 . 1.362(5) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.367(5) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.366(5) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.391(5) ?
    C18 H18 . 0.9300 ?
    C19 H19 . 0.9300 ?
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
    C5 N1 C1 . . 116.4(4) ?
    C13 N2 C9 . . 117.2(4) ?
    C14 N3 C8 . . 122.8(3) ?
    C14 N3 H3N . . 118.6 ?
    C8 N3 H3N . . 118.6 ?
    N1 C1 C2 . . 124.8(5) ?
    N1 C1 H1 . . 117.6 ?
    C2 C1 H1 . . 117.6 ?
    C1 C2 C3 . . 118.4(5) ?
    C1 C2 H2 . . 120.8 ?
    C3 C2 H2 . . 120.8 ?
    C2 C3 C4 . . 118.8(4) ?
    C2 C3 H3 . . 120.6 ?
    C4 C3 H3 . . 120.6 ?
    C3 C4 C5 . . 119.0(4) ?
    C3 C4 H4 . . 120.5 ?
    C5 C4 H4 . . 120.5 ?
    N1 C5 C4 . . 122.5(4) ?
    N1 C5 C6 . . 116.5(4) ?
    C4 C5 C6 . . 121.0(4) ?
    O1 C6 C5 . . 119.8(4) ?
    O1 C6 C7 . . 120.8(4) ?
    C5 C6 C7 . . 119.5(3) ?
    C6 C7 C8 . . 111.9(3) ?
    C6 C7 H7A . . 109.2 ?
    C8 C7 H7A . . 109.2 ?
    C6 C7 H7B . . 109.2 ?
    C8 C7 H7B . . 109.2 ?
    H7A C7 H7B . . 107.9 ?
    N3 C8 C9 . . 114.0(3) ?
    N3 C8 C7 . . 108.5(3) ?
    C9 C8 C7 . . 110.4(3) ?
    N3 C8 H8 . . 107.9 ?
    C9 C8 H8 . . 107.9 ?
    C7 C8 H8 . . 107.9 ?
    N2 C9 C10 . . 122.1(4) ?
    N2 C9 C8 . . 114.5(3) ?
    C10 C9 C8 . . 123.4(3) ?
    C9 C10 C11 . . 119.0(4) ?
    C9 C10 H10 . . 120.5 ?
    C11 C10 H10 . . 120.5 ?
    C12 C11 C10 . . 119.9(4) ?
    C12 C11 H11A . . 120.0 ?
    C10 C11 H11A . . 120.0 ?
    C13 C12 C11 . . 117.2(4) ?
    C13 C12 H12 . . 121.4 ?
    C11 C12 H12 . . 121.4 ?
    N2 C13 C12 . . 124.5(4) ?
    N2 C13 H13 . . 117.7 ?
    C12 C13 H13 . . 117.7 ?
    C19 C14 N3 . . 122.5(3) ?
    C19 C14 C15 . . 118.6(3) ?
    N3 C14 C15 . . 118.9(3) ?
    C16 C15 C14 . . 120.3(3) ?
    C16 C15 H15 . . 119.9 ?
    C14 C15 H15 . . 119.9 ?
    C15 C16 C17 . . 121.9(4) ?
    C15 C16 H16 . . 119.0 ?
    C17 C16 H16 . . 119.0 ?
    C18 C17 C16 . . 118.1(4) ?
    C18 C17 H17 . . 120.9 ?
    C16 C17 H17 . . 120.9 ?
    C17 C18 C19 . . 121.5(4) ?
    C17 C18 H18 . . 119.3 ?
    C19 C18 H18 . . 119.3 ?
    C14 C19 C18 . . 119.6(4) ?
    C14 C19 H19 . . 120.2 ?
    C18 C19 H19 . . 120.2 ?
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
    C5 N1 C1 C2 . . . . -1.0(7) ?
    N1 C1 C2 C3 . . . . 0.7(8) ?
    C1 C2 C3 C4 . . . . 0.0(7) ?
    C2 C3 C4 C5 . . . . -0.3(7) ?
    C1 N1 C5 C4 . . . . 0.7(6) ?
    C1 N1 C5 C6 . . . . -178.4(4) ?
    C3 C4 C5 N1 . . . . -0.1(6) ?
    C3 C4 C5 C6 . . . . 179.0(4) ?
    N1 C5 C6 O1 . . . . 167.1(4) ?
    C4 C5 C6 O1 . . . . -12.0(6) ?
    N1 C5 C6 C7 . . . . -12.3(5) ?
    C4 C5 C6 C7 . . . . 168.6(4) ?
    O1 C6 C7 C8 . . . . 51.2(5) ?
    C5 C6 C7 C8 . . . . -129.4(3) ?
    C14 N3 C8 C9 . . . . 67.7(4) ?
    C14 N3 C8 C7 . . . . -168.8(3) ?
    C6 C7 C8 N3 . . . . 69.9(4) ?
    C6 C7 C8 C9 . . . . -164.4(3) ?
    C13 N2 C9 C10 . . . . 0.6(5) ?
    C13 N2 C9 C8 . . . . -177.4(3) ?
    N3 C8 C9 N2 . . . . -157.1(3) ?
    C7 C8 C9 N2 . . . . 80.3(4) ?
    N3 C8 C9 C10 . . . . 24.8(5) ?
    C7 C8 C9 C10 . . . . -97.7(4) ?
    N2 C9 C10 C11 . . . . -0.2(6) ?
    C8 C9 C10 C11 . . . . 177.7(4) ?
    C9 C10 C11 C12 . . . . -0.8(7) ?
    C10 C11 C12 C13 . . . . 1.3(7) ?
    C9 N2 C13 C12 . . . . 0.0(6) ?
    C11 C12 C13 N2 . . . . -0.9(7) ?
    C8 N3 C14 C19 . . . . 6.6(5) ?
    C8 N3 C14 C15 . . . . -175.7(3) ?
    C19 C14 C15 C16 . . . . 1.5(6) ?
    N3 C14 C15 C16 . . . . -176.3(4) ?
    C14 C15 C16 C17 . . . . -1.0(6) ?
    C15 C16 C17 C18 . . . . 0.0(6) ?
    C16 C17 C18 C19 . . . . 0.6(6) ?
    N3 C14 C19 C18 . . . . 176.7(4) ?
    C15 C14 C19 C18 . . . . -0.9(5) ?
    C17 C18 C19 C14 . . . . -0.1(6) ?
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
    N3 H3N N2 4_646 0.86 2.35 3.191(4) 164.2
    C10 H10 O1 4_646 0.93 2.62 3.398(5) 141.2
    C3 H3 Cg 3_556 0.93 2.77 3.548(5) 141.9
