#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/80/2008073.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
'Sema Öztürk'
'Mehmet Akkurt'
'İbrahim Abdul Razak'
'Hoong-Kun Fun'
'İsmail Yıldırım'
_publ_section_title
;
 5-Benzoyl-1-ethyl-4-phenyl-1H-pyrimidin-2-one
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              97
_journal_page_last               99
_journal_paper_doi               10.1107/S0108270198009822
_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       'ω 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      ?
_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_details
'w = 1/[σ²(Fo²)+(0.0246P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_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)
_cod_data_source_file            fr1134.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0246P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0246P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_Hall     '-P 2yc'
_cod_original_sg_symbol_H-M      'P 21/c'
_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_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_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_site_symmetry_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)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21105618
