##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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                #
#                                                                            #
##############################################################################
                                             
data_V
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
 1-amino-5-benzoyl-4-phenylpyrimidin-2(1H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H13 N3 O2'
_chemical_formula_sum     'C17 H13 N3 O2'
_chemical_formula_weight     291.30
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     11.7547(11)
_cell_length_b     16.6566(11)
_cell_length_c     7.2986(6)
_cell_angle_alpha     90.00
_cell_angle_beta     101.722(7)
_cell_angle_gamma     90.00
_cell_volume     1399.2(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     10310
_cell_measurement_theta_min     1.77
_cell_measurement_theta_max     28.91
_cell_measurement_temperature     296
_exptl_crystal_description     'Prism'
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.61
_exptl_crystal_size_mid     0.46
_exptl_crystal_size_min     0.23
_exptl_crystal_density_diffrn     1.383
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     608
_exptl_absorpt_coefficient_mu     0.094
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed X-ray tube'
_diffrn_radiation_monochromator     'plane graphite'
_diffrn_measurement_device_type     'STOE IPDS-II'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     9982
_diffrn_reflns_av_R_equivalents     0.0289
_diffrn_reflns_av_sigmaI/netI     0.0261
_diffrn_reflns_theta_min     1.77
_diffrn_reflns_theta_max     28.78
_diffrn_reflns_theta_full     28.78
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     22
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     7
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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     3605
_reflns_number_gt     2612
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0547
_refine_ls_R_factor_gt     0.0373
_refine_ls_wR_factor_gt     0.0977
_refine_ls_wR_factor_ref     0.1047
_refine_ls_goodness_of_fit_ref     1.038
_refine_ls_restrained_S_all     1.038
_refine_ls_number_reflns     3605
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0564P)²+0.0428P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.146
_refine_diff_density_min     -0.127
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.033(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                  'Ortep-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 0.58123(8) 0.17479(6) 0.02078(14) 0.0448(2) Uani d . 1 . . N
    N2 0.50825(8) 0.11459(6) 0.26760(14) 0.0421(2) Uani d . 1 . . N
    N3 0.43127(10) 0.11393(7) 0.39451(17) 0.0506(3) Uani d . 1 . . N
    H3A 0.3604(16) 0.1057(9) 0.321(2) 0.070(5) Uiso d . 1 . . H
    H3B 0.4333(15) 0.1657(12) 0.445(3) 0.081(5) Uiso d . 1 . . H
    O1 0.42618(8) 0.22736(5) 0.12324(14) 0.0561(3) Uani d . 1 . . O
    O2 0.72262(9) -0.05651(5) -0.01925(12) 0.0572(3) Uani d . 1 . . O
    C1 0.85852(11) 0.10648(8) -0.0205(2) 0.0522(3) Uani d . 1 . . C
    H1C 0.8822(13) 0.0837(9) 0.103(2) 0.063(4) Uiso d . 1 . . H
    C2 0.94163(13) 0.12410(10) -0.1242(2) 0.0629(4) Uani d . 1 . . C
    H2C 1.0232(18) 0.1119(10) -0.077(3) 0.081(5) Uiso d . 1 . . H
    C3 0.90939(14) 0.15934(9) -0.2974(2) 0.0663(4) Uani d . 1 . . C
    H3C 0.9649(17) 0.1718(11) -0.371(3) 0.092(6) Uiso d . 1 . . H
    C4 0.79406(15) 0.17706(8) -0.3692(2) 0.0616(4) Uani d . 1 . . C
    H4C 0.7692(14) 0.2029(10) -0.490(3) 0.073(5) Uiso d . 1 . . H
    C5 0.71059(12) 0.16006(7) -0.26599(19) 0.0508(3) Uani d . 1 . . C
    H5C 0.6316(13) 0.1735(8) -0.3113(19) 0.050(4) Uiso d . 1 . . H
    C6 0.74220(10) 0.12465(7) -0.09104(17) 0.0429(3) Uani d . 1 . . C
    C7 0.65388(9) 0.11461(6) 0.02669(16) 0.0402(2) Uani d . 1 . . C
    C8 0.50037(9) 0.17586(7) 0.13203(17) 0.0429(3) Uani d . 1 . . C
    C9 0.58059(10) 0.05214(7) 0.27156(17) 0.0419(3) Uani d . 1 . . C
    H9C 0.5739(11) 0.0104(8) 0.3658(19) 0.045(3) Uiso d . 1 . . H
    C10 0.65380(9) 0.04737(7) 0.14822(16) 0.0404(2) Uani d . 1 . . C
    C11 0.71652(10) -0.02907(6) 0.13330(16) 0.0413(2) Uani d . 1 . . C
    C12 0.76959(9) -0.07185(6) 0.30807(16) 0.0391(2) Uani d . 1 . . C
    C13 0.76558(10) -0.15524(7) 0.31283(18) 0.0440(3) Uani d . 1 . . C
    H13C 0.7241(12) -0.1846(8) 0.203(2) 0.051(4) Uiso d . 1 . . H
    C14 0.81859(11) -0.19559(7) 0.4731(2) 0.0503(3) Uani d . 1 . . C
    H14C 0.8149(12) -0.2545(9) 0.479(2) 0.059(4) Uiso d . 1 . . H
    C15 0.87739(12) -0.15385(8) 0.6260(2) 0.0548(3) Uani d . 1 . . C
    H15C 0.9159(14) -0.1825(9) 0.738(2) 0.068(4) Uiso d . 1 . . H
    C16 0.88069(12) -0.07113(9) 0.6228(2) 0.0562(3) Uani d . 1 . . C
    H16C 0.9220(15) -0.0405(10) 0.730(2) 0.074(5) Uiso d . 1 . . H
    C17 0.82607(11) -0.02995(7) 0.46508(18) 0.0487(3) Uani d . 1 . . C
    H17C 0.8269(12) 0.0291(9) 0.4603(19) 0.057(4) Uiso d . 1 . . H
_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
    N1 C7 . 1.3118(14) yes
    N1 C8 . 1.3699(15) yes
    N2 C9 . 1.3401(14) yes
    N2 C8 . 1.4112(15) yes
    N2 N3 . 1.4204(13) yes
    N3 H3A . 0.905(18) ?
    N3 H3B . 0.936(19) ?
    O1 C8 . 1.2157(13) yes
    O2 C11 . 1.2191(14) yes
    C1 C2 . 1.3835(19) ?
    C1 C6 . 1.3929(17) ?
    C1 H1C . 0.966(16) ?
    C2 C3 . 1.375(2) ?
    C2 H2C . 0.97(2) ?
    C3 C4 . 1.382(2) ?
    C3 H3C . 0.95(2) ?
    C4 C5 . 1.3824(19) ?
    C4 H4C . 0.968(18) ?
    C5 C6 . 1.3870(17) ?
    C5 H5C . 0.947(14) ?
    C6 C7 . 1.4855(15) yes
    C7 C10 . 1.4289(15) ?
    C9 C10 . 1.3683(15) ?
    C9 H9C . 0.993(13) ?
    C10 C11 . 1.4863(15) yes
    C11 C12 . 1.4835(16) yes
    C12 C17 . 1.3899(17) ?
    C12 C13 . 1.3905(16) ?
    C13 C14 . 1.3825(18) ?
    C13 H13C . 0.982(14) ?
    C14 C15 . 1.376(2) ?
    C14 H14C . 0.983(15) ?
    C15 C16 . 1.379(2) ?
    C15 H15C . 0.975(17) ?
    C16 C17 . 1.3814(19) ?
    C16 H16C . 0.979(17) ?
    C17 H17C . 0.984(15) ?
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
    C7 N1 C8 . . 121.05(10) ?
    C9 N2 C8 . . 121.83(10) yes
    C9 N2 N3 . . 117.73(10) yes
    C8 N2 N3 . . 120.20(9) ?
    N2 N3 H3A . . 104.2(11) ?
    N2 N3 H3B . . 106.3(11) ?
    H3A N3 H3B . . 108.6(15) ?
    C2 C1 C6 . . 120.07(14) ?
    C2 C1 H1C . . 119.5(9) ?
    C6 C1 H1C . . 120.4(9) ?
    C3 C2 C1 . . 120.00(14) ?
    C3 C2 H2C . . 118.9(11) ?
    C1 C2 H2C . . 121.1(11) ?
    C2 C3 C4 . . 120.38(13) ?
    C2 C3 H3C . . 121.3(12) ?
    C4 C3 H3C . . 118.3(12) ?
    C5 C4 C3 . . 119.97(15) ?
    C5 C4 H4C . . 117.9(10) ?
    C3 C4 H4C . . 122.1(10) ?
    C4 C5 C6 . . 120.11(13) ?
    C4 C5 H5C . . 121.0(8) ?
    C6 C5 H5C . . 118.8(8) ?
    C5 C6 C1 . . 119.46(11) ?
    C5 C6 C7 . . 119.50(11) ?
    C1 C6 C7 . . 120.72(11) ?
    N1 C7 C10 . . 122.47(10) ?
    N1 C7 C6 . . 114.95(10) ?
    C10 C7 C6 . . 122.41(10) ?
    O1 C8 N1 . . 123.68(11) yes
    O1 C8 N2 . . 119.44(11) yes
    N1 C8 N2 . . 116.84(9) ?
    N2 C9 C10 . . 120.80(11) ?
    N2 C9 H9C . . 114.8(7) ?
    C10 C9 H9C . . 124.4(7) ?
    C9 C10 C7 . . 116.27(10) y
    C9 C10 C11 . . 119.06(10) ?
    C7 C10 C11 . . 124.27(10) y
    O2 C11 C12 . . 120.85(10) ?
    O2 C11 C10 . . 120.68(11) yes
    C12 C11 C10 . . 118.46(9) yes
    C17 C12 C13 . . 119.60(11) ?
    C17 C12 C11 . . 120.98(10) ?
    C13 C12 C11 . . 119.39(10) ?
    C14 C13 C12 . . 119.67(12) ?
    C14 C13 H13C . . 121.0(8) ?
    C12 C13 H13C . . 119.4(8) ?
    C15 C14 C13 . . 120.43(12) ?
    C15 C14 H14C . . 119.3(9) ?
    C13 C14 H14C . . 120.2(9) ?
    C14 C15 C16 . . 120.16(13) ?
    C14 C15 H15C . . 120.2(9) ?
    C16 C15 H15C . . 119.6(9) ?
    C15 C16 C17 . . 120.02(13) ?
    C15 C16 H16C . . 121.2(10) ?
    C17 C16 H16C . . 118.7(10) ?
    C16 C17 C12 . . 120.08(12) ?
    C16 C17 H17C . . 121.3(8) ?
    C12 C17 H17C . . 118.6(8) ?
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 C1 C2 C3 . . . . -0.2(2) ?
    C1 C2 C3 C4 . . . . -0.3(2) ?
    C2 C3 C4 C5 . . . . 0.6(2) ?
    C3 C4 C5 C6 . . . . -0.5(2) ?
    C4 C5 C6 C1 . . . . 0.04(18) ?
    C4 C5 C6 C7 . . . . 173.57(11) ?
    C2 C1 C6 C5 . . . . 0.33(19) ?
    C2 C1 C6 C7 . . . . -173.12(12) ?
    C8 N1 C7 C10 . . . . -0.24(17) ?
    C8 N1 C7 C6 . . . . -175.58(10) ?
    C5 C6 C7 N1 . . . . -38.95(15) ?
    C1 C6 C7 N1 . . . . 134.50(12) y
    C5 C6 C7 C10 . . . . 145.71(12) y
    C1 C6 C7 C10 . . . . -40.84(17) ?
    C7 N1 C8 O1 . . . . -174.93(11) ?
    C7 N1 C8 N2 . . . . 7.36(16) ?
    C9 N2 C8 O1 . . . . 173.33(11) ?
    N3 N2 C8 O1 . . . . -0.98(17) ?
    C9 N2 C8 N1 . . . . -8.86(16) ?
    N3 N2 C8 N1 . . . . 176.83(10) ?
    C8 N2 C9 C10 . . . . 2.95(17) ?
    N3 N2 C9 C10 . . . . 177.40(11) ?
    N2 C9 C10 C7 . . . . 4.23(16) ?
    N2 C9 C10 C11 . . . . -168.85(11) ?
    N1 C7 C10 C9 . . . . -5.75(17) ?
    C6 C7 C10 C9 . . . . 169.24(10) ?
    N1 C7 C10 C11 . . . . 166.92(11) ?
    C6 C7 C10 C11 . . . . -18.09(17) ?
    C9 C10 C11 O2 . . . . 135.53(12) yes
    C7 C10 C11 O2 . . . . -36.96(17) yes
    C9 C10 C11 C12 . . . . -43.39(15) ?
    C7 C10 C11 C12 . . . . 144.13(11) ?
    O2 C11 C12 C17 . . . . 140.80(12) yes
    C10 C11 C12 C17 . . . . -40.29(15) yes
    O2 C11 C12 C13 . . . . -37.33(16) ?
    C10 C11 C12 C13 . . . . 141.58(11) ?
    C17 C12 C13 C14 . . . . -0.52(17) ?
    C11 C12 C13 C14 . . . . 177.63(10) ?
    C12 C13 C14 C15 . . . . -1.46(18) ?
    C13 C14 C15 C16 . . . . 2.1(2) ?
    C14 C15 C16 C17 . . . . -0.8(2) ?
    C15 C16 C17 C12 . . . . -1.2(2) ?
    C13 C12 C17 C16 . . . . 1.86(18) ?
    C11 C12 C17 C16 . . . . -176.27(11) ?
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 H3A O2 3_655 0.91(2) 2.37(2) 3.110(2) 140.0(10)
    N3 H3B O1 4_566 0.92(2) 2.22(2) 3.134(2) 166(2)
    N3 H3A CgP 3_656 0.91(2) 2.90(2) 3.3410(10)
                                              112.0(10)
    C3 H3C CgP 3_755 0.95(2) 2.90(2) 3.692(2) 142(2)
data_global
_journal_date_recd_electronic     2004-11-15
_journal_date_accepted     2004-11-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue     12
_journal_page_first     o2476
_journal_page_last     o2478
_journal_paper_category     EO
_publ_contact_author_name     'Necmi Dege'
_publ_contact_author_address
;
 University of Ondokuz Mayıs
 Faculty of Arts and Sciences
 Department of Physics
 55139-Samsun
 Turkey
;
_publ_contact_author_email     dege@omu.edu.tr
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
 1-amino-5-benzoyl-4-phenylpyrimidin-2(1H)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Dege, Necmi'
;   University of Ondokuz Mayıs
    Faculty of Arts and Sciences
    Department of Physics
    55139-Samsun
    Turkey
;
    'Şekerci, Memet'
;    Fırat University
     Arts and Sciences Faculty
     Department of Chemistry
     23119-Elazıg̃
     Turkey
;
    'Çetin, Ahmet'
;    Fırat University
     Arts and Sciences Faculty
     Department of Chemistry
     23119-Elazıg̃
     Turkey
;
    'Dinçer, Muharrem'
;   University of Ondokuz Mayıs
    Faculty of Arts and Sciences
    Department of Physics
    55139-Samsun
    Turkey
;
    'Gülcan, Mehmet'
;    Fırat University
     Arts and Sciences Faculty
     Department of Chemistry
     23119-Elazıg̃
     Turkey
;
    'Cansız,  Ahmet'
;    Fırat University
     Arts and Sciences Faculty
     Department of Chemistry
     23119-Elazıg̃
     Turkey
;
    'Büyükgüngör, Orhan'
;   University of Ondokuz Mayıs
    Faculty of Arts and Sciences
    Department of Physics
    55139-Samsun
    Turkey
;
