#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/46/2204649.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_2204649
loop_
_publ_author_name
'Dege, Necmi'
'Şekerci, Memet'
'Çetin, Ahmet'
'Dinçer, Muharrem'
'Gülcan, Mehmet'
'Cansız,  Ahmet'
'Büyükgüngör, Orhan'
_publ_section_title
;
 1-Amino-5-benzoyl-4-phenylpyrimidin-2(1H)-one
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2476
_journal_page_last               o2478
_journal_paper_doi               10.1107/S1600536804030338
_journal_volume                  60
_journal_year                    2004
_chemical_formula_moiety         'C17 H13 N3 O2'
_chemical_formula_sum            'C17 H13 N3 O2'
_chemical_formula_weight         291.30
_chemical_name_systematic
;
 1-amino-5-benzoyl-4-phenylpyrimidin-2(1H)-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.722(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7547(11)
_cell_length_b                   16.6566(11)
_cell_length_c                   7.2986(6)
_cell_measurement_reflns_used    10310
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.91
_cell_measurement_theta_min      1.77
_cell_volume                     1399.2(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'STOE IPDS-II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9982
_diffrn_reflns_theta_full        28.78
_diffrn_reflns_theta_max         28.78
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.127
_refine_ls_extinction_coef       0.033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0564P)²+0.0428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                2612
_reflns_number_total             3605
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ci6491.cif
_cod_data_source_block           V
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204649
_cod_database_fobs_code          2204649
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_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_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
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_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_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)
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
_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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10592139
2 PubChem 14472001
