#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008073.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_2008073
loop_
_publ_author_name
'\"Ozt\"urk, S.'
'Akkurt, M.'
'Razak, I. A.'
'Fun, H.-K.'
'Yildirim, \.I.'
_publ_section_title
;
 5-Benzoyl-1-ethyl-4-phenyl-1<i>H</i>-pyrimidin-2-one
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              97
_journal_page_last               99
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34
_chemical_melting_point          179
_chemical_name_systematic
;
5-benzoyl-1-ethyl-4-phenylpyrimidine-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 96.164(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4254(4)
_cell_length_b                   17.2278(6)
_cell_length_c                   10.9291(3)
_cell_measurement_reflns_used    1489
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33
_cell_measurement_theta_min      1.5
_cell_volume                     1577.20(10)
_computing_cell_refinement       'SAINT (Siemens, 1996b)'
_computing_data_collection       'SMART (Siemens, 1996a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
; SHELXTL and
  PARST (Nardelli, 1995)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1996)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device
;
Siemens SMART CCD area-detector diffractometer
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_av_sigmaI/netI    0.1360
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8150
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.172
_refine_ls_extinction_coef       0.0157(17)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.009
_refine_ls_goodness_of_fit_obs   1.204
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_restrained_S_obs      1.204
_refine_ls_R_factor_all          0.1788
_refine_ls_R_factor_obs          0.0677
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0246P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1210
_refine_ls_wR_factor_obs         0.0905
_reflns_number_observed          1241
_reflns_number_total             2756
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fr1134.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_Hall '-P 2yc'
_cod_database_code               2008073
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'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.052(2) 0.095(2) 0.042(2) -0.016(2) 0.0173(14) 0.0038(15)
O2 0.041(2) 0.080(2) 0.053(2) 0.015(2) 0.0062(14) 0.002(2)
N1 0.034(2) 0.063(2) 0.035(2) -0.004(2) 0.006(2) -0.004(2)
N2 0.037(2) 0.054(2) 0.038(2) -0.005(2) 0.009(2) 0.001(2)
C1 0.041(3) 0.053(3) 0.030(2) 0.007(2) 0.006(2) 0.001(2)
C2 0.045(3) 0.055(3) 0.037(3) 0.001(2) 0.013(2) -0.001(2)
C3 0.036(2) 0.040(2) 0.038(2) 0.004(2) 0.006(2) 0.003(2)
C4 0.034(2) 0.043(2) 0.036(2) 0.004(2) 0.007(2) 0.005(2)
C5 0.042(2) 0.043(2) 0.044(3) 0.000(2) 0.008(2) 0.004(2)
C6 0.042(2) 0.039(2) 0.039(2) -0.002(2) 0.010(2) 0.002(2)
C7 0.055(3) 0.040(2) 0.045(3) -0.003(2) 0.020(2) -0.001(2)
C8 0.080(3) 0.042(3) 0.041(3) -0.010(2) 0.024(3) -0.005(2)
C9 0.087(4) 0.060(3) 0.034(3) -0.016(3) 0.003(3) 0.004(3)
C10 0.071(3) 0.061(3) 0.044(3) 0.008(3) 0.006(3) 0.006(2)
C11 0.060(3) 0.054(3) 0.031(3) 0.005(2) 0.011(2) 0.000(2)
C12 0.036(2) 0.047(2) 0.039(2) 0.000(2) 0.009(2) -0.002(2)
C13 0.042(3) 0.054(3) 0.050(3) -0.012(2) 0.001(2) 0.001(2)
C14 0.059(3) 0.079(4) 0.055(4) -0.006(3) -0.008(3) 0.000(3)
C15 0.059(3) 0.073(3) 0.075(4) -0.029(3) 0.004(3) -0.006(3)
C16 0.067(3) 0.063(3) 0.060(4) -0.022(3) 0.012(3) 0.006(3)
C17 0.046(3) 0.055(3) 0.044(3) -0.005(2) 0.007(2) 0.003(2)
C18 0.036(3) 0.081(4) 0.054(3) -0.007(2) 0.009(2) -0.006(3)
C19 0.056(4) 0.086(4) 0.098(5) -0.022(3) 0.010(3) -0.014(4)
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_occupancy
_atom_site_type_symbol
O1 0.1722(3) 0.6959(2) 0.1731(2) 0.0621(9) Uani d 1 O
O2 -0.3181(3) 0.68199(15) 0.5307(2) 0.0579(8) Uani d 1 O
N1 0.1660(3) 0.6809(2) 0.3790(3) 0.0436(8) Uani d 1 N
N2 -0.0530(3) 0.6421(2) 0.2370(3) 0.0425(9) Uani d 1 N
C1 0.0767(5) 0.6713(2) 0.4727(4) 0.0411(10) Uani d 1 C
C2 0.0970(4) 0.6747(2) 0.2564(3) 0.0449(10) Uani d 1 C
C3 -0.1364(4) 0.6293(2) 0.3294(3) 0.0376(10) Uani d 1 C
C4 -0.0786(4) 0.6479(2) 0.4532(3) 0.0375(9) Uani d 1 C
C5 -0.1835(5) 0.6555(2) 0.5538(3) 0.0428(10) Uani d 1 C
C6 -0.1225(4) 0.6350(2) 0.6816(3) 0.0396(10) Uani d 1 C
C7 -0.1861(5) 0.6721(2) 0.7792(4) 0.0457(11) Uani d 1 C
C8 -0.1331(6) 0.6538(2) 0.8995(4) 0.0534(12) Uani d 1 C
C9 -0.0210(6) 0.5971(3) 0.9241(4) 0.0606(13) Uani d 1 C
C10 0.0406(6) 0.5586(3) 0.8290(4) 0.0586(13) Uani d 1 C
C11 -0.0077(5) 0.5783(2) 0.7092(4) 0.0478(11) Uani d 1 C
C12 -0.2909(4) 0.5888(2) 0.2964(3) 0.0403(10) Uani d 1 C
C13 -0.3800(5) 0.6048(2) 0.1848(4) 0.0491(11) Uani d 1 C
C14 -0.5171(6) 0.5630(3) 0.1498(5) 0.0654(14) Uani d 1 C
C15 -0.5650(6) 0.5045(3) 0.2226(5) 0.0690(14) Uani d 1 C
C16 -0.4770(6) 0.4873(3) 0.3324(5) 0.0628(13) Uani d 1 C
C17 -0.3424(5) 0.5297(2) 0.3691(4) 0.0483(11) Uani d 1 C
C18 0.3358(5) 0.7040(3) 0.4036(5) 0.0566(13) Uani d 1 C
C19 0.3594(7) 0.7899(3) 0.3904(7) 0.080(2) Uani d 1 C
H1 0.129(3) 0.6846(15) 0.551(3) 0.025(9) Uiso d 1 H
H7 -0.269(3) 0.7092(16) 0.758(3) 0.033(10) Uiso d 1 H
H8 -0.182(4) 0.6816(19) 0.971(3) 0.071(12) Uiso d 1 H
H9 0.025(4) 0.584(2) 1.006(4) 0.085(15) Uiso d 1 H
H10 0.119(4) 0.5214(19) 0.850(3) 0.052(12) Uiso d 1 H
H11 0.033(4) 0.5530(17) 0.640(3) 0.048(10) Uiso d 1 H
H13 -0.343(4) 0.6492(18) 0.133(3) 0.055(11) Uiso d 1 H
H14 -0.570(4) 0.576(2) 0.080(3) 0.064(15) Uiso d 1 H
H15 -0.669(5) 0.478(2) 0.196(4) 0.087(15) Uiso d 1 H
H16 -0.510(4) 0.446(2) 0.381(3) 0.076(14) Uiso d 1 H
H17 -0.278(4) 0.5200(19) 0.446(3) 0.051(12) Uiso d 1 H
H18B 0.387(4) 0.6780(19) 0.342(3) 0.059(12) Uiso d 1 H
H18A 0.363(4) 0.685(2) 0.488(4) 0.069(14) Uiso d 1 H
H19A 0.298(9) 0.818(4) 0.447(7) 0.23(4) Uiso d 1 H
H19B 0.477(6) 0.802(2) 0.407(4) 0.099(16) Uiso d 1 H
H19C 0.335(5) 0.805(3) 0.300(5) 0.11(2) Uiso d 1 H
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
_geom_angle_publ_flag
C1 N1 C2 120.6(3) ?
C1 N1 C18 120.2(4) ?
C2 N1 C18 119.0(3) ?
C3 N2 C2 120.7(3) ?
N1 C1 C4 121.5(4) ?
N1 C1 H1 114.7(16) ?
C4 C1 H1 123.7(16) ?
O1 C2 N2 123.3(4) yes
O1 C2 N1 119.6(4) yes
N2 C2 N1 117.1(3) ?
N2 C3 C4 122.4(3) ?
N2 C3 C12 114.9(3) yes
C4 C3 C12 122.5(3) ?
C1 C4 C3 116.1(3) ?
C1 C4 C5 119.6(3) ?
C3 C4 C5 123.5(3) ?
O2 C5 C6 120.3(3) ?
O2 C5 C4 119.5(3) ?
C6 C5 C4 120.2(3) yes
C11 C6 C7 118.1(4) ?
C11 C6 C5 122.6(3) ?
C7 C6 C5 119.3(4) ?
C8 C7 C6 120.8(4) ?
C8 C7 H7 122.2(18) ?
C6 C7 H7 117.0(18) ?
C9 C8 C7 119.9(4) ?
C9 C8 H8 120.(2) ?
C7 C8 H8 120.(2) ?
C8 C9 C10 120.2(5) ?
C8 C9 H9 124.(2) ?
C10 C9 H9 116.(2) ?
C11 C10 C9 120.2(5) ?
C11 C10 H10 122.(2) ?
C9 C10 H10 118.(2) ?
C10 C11 C6 120.8(4) ?
C10 C11 H11 122.8(19) ?
C6 C11 H11 116.(2) ?
C17 C12 C13 118.4(4) ?
C17 C12 C3 121.6(4) ?
C13 C12 C3 119.7(3) ?
C14 C13 C12 119.8(4) ?
C14 C13 H13 122.4(19) ?
C12 C13 H13 117.8(19) ?
C15 C14 C13 120.8(5) ?
C15 C14 H14 123.(3) ?
C13 C14 H14 116.(3) ?
C14 C15 C16 120.0(5) ?
C14 C15 H15 118.(2) ?
C16 C15 H15 122.(2) ?
C17 C16 C15 119.5(5) ?
C17 C16 H16 121.(2) ?
C15 C16 H16 119.(2) ?
C16 C17 C12 121.4(5) ?
C16 C17 H17 122.(2) ?
C12 C17 H17 117.(2) ?
N1 C18 C19 112.5(4) yes
N1 C18 H18B 104.(2) ?
C19 C18 H18B 109.(2) ?
N1 C18 H18A 102.(2) ?
C19 C18 H18A 113.(2) ?
H18B C18 H18A 116.(3) ?
C18 C19 H19A 110.(4) ?
C18 C19 H19B 109.(3) ?
H19A C19 H19B 111.(5) ?
C18 C19 H19C 109.(3) ?
H19A C19 H19C 115.(5) ?
H19B C19 H19C 103.(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.220(4) yes
O2 C5 1.223(4) yes
N1 C1 1.344(4) yes
N1 C2 1.406(4) yes
N1 C18 1.482(5) yes
N2 C3 1.310(4) yes
N2 C2 1.378(4) yes
C1 C4 1.364(5) ?
C1 H1 0.95(3) ?
C3 C4 1.424(4) ?
C3 C12 1.487(5) ?
C4 C5 1.489(4) ?
C5 C6 1.478(5) ?
C6 C11 1.386(5) ?
C6 C7 1.399(4) ?
C7 C8 1.378(5) ?
C7 H7 0.96(3) ?
C8 C9 1.366(6) ?
C8 H8 1.04(3) ?
C9 C10 1.380(5) ?
C9 H9 0.97(4) ?
C10 C11 1.371(5) ?
C10 H10 0.93(3) ?
C11 H11 0.97(3) ?
C12 C17 1.389(5) ?
C12 C13 1.390(5) ?
C13 C14 1.380(5) ?
C13 H13 1.02(3) ?
C14 C15 1.371(6) ?
C14 H14 0.88(4) ?
C15 C16 1.373(6) ?
C15 H15 1.00(4) ?
C16 C17 1.372(6) ?
C16 H16 0.95(4) ?
C17 H17 0.96(3) ?
C18 C19 1.502(7) ?
C18 H18B 0.95(3) ?
C18 H18A 0.98(4) ?
C19 H19A 0.97(7) ?
C19 H19B 1.01(5) ?
C19 H19C 1.02(5) ?
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
C18 H18B O1 1_555 0.95(4) 2.46(3) 2.742(5) 97(2) no
C1 H1 O1 4_565 0.95(3) 2.46(3) 3.209(5) 136(2) no
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
C2 N1 C1 C4 6.7(5)
C18 N1 C1 C4 -178.1(4)
C3 N2 C2 O1 -171.5(3)
C3 N2 C2 N1 10.7(5)
C1 N1 C2 O1 167.9(3)
C18 N1 C2 O1 -7.3(5)
C1 N1 C2 N2 -14.1(5)
C18 N1 C2 N2 170.6(3)
C2 N2 C3 C4 0.0(5)
C2 N2 C3 C12 -175.8(3)
N1 C1 C4 C3 4.0(5)
N1 C1 C4 C5 -165.9(3)
N2 C3 C4 C1 -7.6(5)
C12 C3 C4 C1 168.0(3)
N2 C3 C4 C5 161.8(3)
C12 C3 C4 C5 -22.6(5)
C1 C4 C5 O2 134.6(4)
C3 C4 C5 O2 -34.5(5)
C1 C4 C5 C6 -42.4(5)
C3 C4 C5 C6 148.5(3)
O2 C5 C6 C11 152.7(3)
C4 C5 C6 C11 -30.4(5)
O2 C5 C6 C7 -25.1(5)
C4 C5 C6 C7 151.8(3)
C11 C6 C7 C8 1.5(5)
C5 C6 C7 C8 179.4(3)
C6 C7 C8 C9 -2.2(6)
C7 C8 C9 C10 0.7(6)
C8 C9 C10 C11 1.4(6)
C9 C10 C11 C6 -2.2(6)
C7 C6 C11 C10 0.7(5)
C5 C6 C11 C10 -177.1(4)
N2 C3 C12 C17 137.6(3)
C4 C3 C12 C17 -38.3(5)
N2 C3 C12 C13 -36.3(5)
C4 C3 C12 C13 147.8(3)
C17 C12 C13 C14 0.8(5)
C3 C12 C13 C14 174.9(3)
C12 C13 C14 C15 -1.3(6)
C13 C14 C15 C16 0.5(7)
C14 C15 C16 C17 0.8(7)
C15 C16 C17 C12 -1.3(6)
C13 C12 C17 C16 0.5(5)
C3 C12 C17 C16 -173.5(3)
C1 N1 C18 C19 -96.5(5)
C2 N1 C18 C19 78.7(5)