#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/95/2229519.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_2229519
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Chanawanno, Kullapa'
'Chantrapromma, Suchada'
_publ_section_title
;
 2-(2-Hydroxy-3-methoxyphenyl)-6H-perimidin-6-one
;
_journal_coeditor_code           SJ5107
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o715
_journal_page_last               o716
_journal_paper_doi               10.1107/S1600536811006465
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H12 N2 O3'
_chemical_formula_moiety         'C18 H12 N2 O3'
_chemical_formula_sum            'C18 H12 N2 O3'
_chemical_formula_weight         304.30
_chemical_melting_point_gt       507
_chemical_melting_point_lt       508
_chemical_name_systematic
;
2-(2-Hydroxy-3-methoxyphenyl)-6H-perimidin-6-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 94.373(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.4718(17)
_cell_length_b                   7.0666(3)
_cell_length_c                   15.0815(6)
_cell_measurement_reflns_used    6529
_cell_measurement_temperature    100
_cell_measurement_theta_max      36.30
_cell_measurement_theta_min      1.60
_cell_volume                     2706.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            42939
_diffrn_reflns_theta_full        36.30
_diffrn_reflns_theta_max         36.30
_diffrn_reflns_theta_min         1.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_correction_T_min  0.9334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         6529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1100P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.2095
_reflns_number_gt                3471
_reflns_number_total             6529
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5107.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2229519
_cod_database_fobs_code          2229519
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 1.20986(4) 0.86652(17) 0.36853(7) 0.0390(3) Uani d . 1 . .
O O2 0.93604(4) 0.76137(15) 0.66009(7) 0.0305(2) Uani d . 1 . .
H H1O2 0.9692(9) 0.784(3) 0.6441(15) 0.068(7) Uiso d . 1 . .
O O3 0.83728(4) 0.69274(15) 0.67439(7) 0.0307(2) Uani d . 1 . .
N N1 1.00314(4) 0.71962(15) 0.40931(7) 0.0230(2) Uani d . 1 . .
N N2 1.01534(4) 0.77988(14) 0.56606(7) 0.0217(2) Uani d . 1 . .
C C1 0.92971(5) 0.68964(16) 0.50224(9) 0.0213(2) Uani d . 1 . .
C C2 0.90819(5) 0.70778(17) 0.58472(9) 0.0229(3) Uani d . 1 . .
C C3 0.85404(5) 0.66982(18) 0.59105(9) 0.0245(3) Uani d . 1 . .
C C4 0.82297(5) 0.61425(18) 0.51641(10) 0.0269(3) Uani d . 1 . .
H H4 0.7846(8) 0.588(3) 0.5190(13) 0.053(5) Uiso d . 1 . .
C C5 0.84470(5) 0.59241(19) 0.43503(9) 0.0271(3) Uani d . 1 . .
H H5 0.8242(6) 0.542(2) 0.3839(11) 0.032(4) Uiso d . 1 . .
C C6 0.89730(5) 0.62922(18) 0.42762(9) 0.0242(3) Uani d . 1 . .
H H6 0.9121(6) 0.608(3) 0.3716(12) 0.039(5) Uiso d . 1 . .
C C7 0.98576(5) 0.73220(16) 0.49261(9) 0.0208(2) Uani d . 1 . .
C C8 1.05351(5) 0.75829(17) 0.40160(9) 0.0222(2) Uani d . 1 . .
C C9 1.07449(5) 0.7429(2) 0.31468(9) 0.0271(3) Uani d . 1 . .
H H9 1.0495(6) 0.696(2) 0.2625(11) 0.027(4) Uiso d . 1 . .
C C10 1.12551(5) 0.7780(2) 0.30472(9) 0.0281(3) Uani d . 1 . .
H H10 1.1420(6) 0.761(2) 0.2446(11) 0.031(4) Uiso d . 1 . .
C C11 1.16293(5) 0.83502(19) 0.37912(9) 0.0269(3) Uani d . 1 . .
C C12 1.14203(5) 0.84961(17) 0.46741(9) 0.0233(3) Uani d . 1 . .
C C13 1.17405(5) 0.89476(19) 0.54295(9) 0.0268(3) Uani d . 1 . .
H H13 1.2155(6) 0.916(2) 0.5341(11) 0.032 Uiso d . 1 . .
C C14 1.15283(5) 0.90293(19) 0.62651(10) 0.0284(3) Uani d . 1 . .
H H14 1.1753(6) 0.931(2) 0.6784(10) 0.029(4) Uiso d . 1 . .
C C15 1.10056(5) 0.86583(18) 0.63559(9) 0.0257(3) Uani d . 1 . .
H H15 1.0859(6) 0.865(2) 0.6931(12) 0.036(4) Uiso d . 1 . .
C C16 1.06736(5) 0.81935(16) 0.55893(9) 0.0218(2) Uani d . 1 . .
C C17 1.08818(5) 0.81121(16) 0.47560(8) 0.0206(2) Uani d . 1 . .
C C18 0.78320(6) 0.6497(2) 0.68447(12) 0.0338(3) Uani d . 1 . .
H H18A 0.7621(7) 0.737(3) 0.6464(12) 0.039(5) Uiso d . 1 . .
H H18B 0.7746(6) 0.521(3) 0.6683(10) 0.032(4) Uiso d . 1 . .
H H18C 0.7805(7) 0.666(2) 0.7467(12) 0.035(4) Uiso d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O2 H1O2 . . 105.4(14) ?
C3 O3 C18 . . 116.32(11) ?
C8 N1 C7 . . 116.80(11) ?
C7 N2 C16 . . 118.40(11) ?
C2 C1 C6 . . 119.38(11) ?
C2 C1 C7 . . 120.97(11) ?
C6 C1 C7 . . 119.65(11) ?
O2 C2 C1 . . 123.88(11) ?
O2 C2 C3 . . 116.70(11) ?
C1 C2 C3 . . 119.41(12) ?
O3 C3 C4 . . 125.62(12) ?
O3 C3 C2 . . 114.43(12) ?
C4 C3 C2 . . 119.95(12) ?
C3 C4 C5 . . 120.50(12) ?
C3 C4 H4 . . 121.5(11) ?
C5 C4 H4 . . 118.0(11) ?
C6 C5 C4 . . 120.32(13) ?
C6 C5 H5 . . 118.3(9) ?
C4 C5 H5 . . 121.2(9) ?
C5 C6 C1 . . 120.42(12) ?
C5 C6 H6 . . 119.3(10) ?
C1 C6 H6 . . 120.2(10) ?
N2 C7 N1 . . 125.29(11) ?
N2 C7 C1 . . 117.29(11) ?
N1 C7 C1 . . 117.42(11) ?
N1 C8 C17 . . 122.25(12) ?
N1 C8 C9 . . 119.17(12) ?
C17 C8 C9 . . 118.57(11) ?
C10 C9 C8 . . 120.76(13) ?
C10 C9 H9 . . 121.4(9) ?
C8 C9 H9 . . 117.7(9) ?
C9 C10 C11 . . 122.77(12) ?
C9 C10 H10 . . 122.6(9) ?
C11 C10 H10 . . 114.6(9) ?
O1 C11 C10 . . 121.75(12) ?
O1 C11 C12 . . 121.49(13) ?
C10 C11 C12 . . 116.75(11) ?
C13 C12 C17 . . 119.11(12) ?
C13 C12 C11 . . 121.84(12) ?
C17 C12 C11 . . 119.03(12) ?
C12 C13 C14 . . 120.14(12) ?
C12 C13 H13 . . 116.6(8) ?
C14 C13 H13 . . 123.2(8) ?
C15 C14 C13 . . 121.45(13) ?
C15 C14 H14 . . 118.9(9) ?
C13 C14 H14 . . 119.6(9) ?
C14 C15 C16 . . 119.02(12) ?
C14 C15 H15 . . 122.2(10) ?
C16 C15 H15 . . 118.7(10) ?
N2 C16 C17 . . 119.84(11) ?
N2 C16 C15 . . 120.32(11) ?
C17 C16 C15 . . 119.84(11) ?
C16 C17 C12 . . 120.44(12) ?
C16 C17 C8 . . 117.41(11) ?
C12 C17 C8 . . 122.12(11) ?
O3 C18 H18A . . 107.1(10) ?
O3 C18 H18B . . 112.2(9) ?
H18A C18 H18B . . 110.1(14) ?
O3 C18 H18C . . 102.7(10) ?
H18A C18 H18C . . 115.0(15) ?
H18B C18 H18C . . 109.5(14) ?
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 C11 . 1.2384(16) ?
O2 C2 . 1.3474(16) ?
O2 H1O2 . 0.91(2) ?
O3 C3 . 1.3676(16) ?
O3 C18 . 1.4301(16) ?
N1 C8 . 1.3256(16) ?
N1 C7 . 1.3663(17) ?
N2 C7 . 1.3345(17) ?
N2 C16 . 1.3664(16) ?
C1 C2 . 1.4030(18) ?
C1 C6 . 1.4102(19) ?
C1 C7 . 1.4769(17) ?
C2 C3 . 1.4155(17) ?
C3 C4 . 1.3827(19) ?
C4 C5 . 1.393(2) ?
C4 H4 . 1.000(19) ?
C5 C6 . 1.3777(18) ?
C5 H5 . 0.966(16) ?
C6 H6 . 0.963(18) ?
C8 C17 . 1.4196(18) ?
C8 C9 . 1.4568(19) ?
C9 C10 . 1.3427(19) ?
C9 H9 . 1.028(16) ?
C10 C11 . 1.472(2) ?
C10 H10 . 1.035(17) ?
C11 C12 . 1.4747(18) ?
C12 C13 . 1.3868(19) ?
C12 C17 . 1.4127(17) ?
C13 C14 . 1.4098(19) ?
C13 H13 . 1.085(16) ?
C14 C15 . 1.3739(18) ?
C14 H14 . 0.955(15) ?
C15 C16 . 1.4179(18) ?
C15 H15 . 0.970(17) ?
C16 C17 . 1.4019(18) ?
C18 H18A . 0.976(18) ?
C18 H18B . 0.963(17) ?
C18 H18C . 0.954(18) ?
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
O2 H1O2 N2 1_555 0.91(2) 1.73(2) 2.5583(15) 151(2) y
C15 H15 O2 2_756 0.970(18) 2.437(18) 3.3686(17) 160.8(12) y
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 O2 . . . . 178.87(11) ?
C7 C1 C2 O2 . . . . -0.90(19) ?
C6 C1 C2 C3 . . . . -1.62(18) ?
C7 C1 C2 C3 . . . . 178.60(10) ?
C18 O3 C3 C4 . . . . 1.88(19) ?
C18 O3 C3 C2 . . . . -177.96(12) ?
O2 C2 C3 O3 . . . . -0.19(17) ?
C1 C2 C3 O3 . . . . -179.73(10) ?
O2 C2 C3 C4 . . . . 179.96(11) ?
C1 C2 C3 C4 . . . . 0.42(18) ?
O3 C3 C4 C5 . . . . -178.86(12) ?
C2 C3 C4 C5 . . . . 0.98(19) ?
C3 C4 C5 C6 . . . . -1.1(2) ?
C4 C5 C6 C1 . . . . -0.1(2) ?
C2 C1 C6 C5 . . . . 1.47(18) ?
C7 C1 C6 C5 . . . . -178.75(11) ?
C16 N2 C7 N1 . . . . -0.21(18) ?
C16 N2 C7 C1 . . . . 179.80(10) ?
C8 N1 C7 N2 . . . . -0.03(18) ?
C8 N1 C7 C1 . . . . 179.96(10) ?
C2 C1 C7 N2 . . . . 2.97(17) ?
C6 C1 C7 N2 . . . . -176.80(11) ?
C2 C1 C7 N1 . . . . -177.02(10) ?
C6 C1 C7 N1 . . . . 3.21(16) ?
C7 N1 C8 C17 . . . . -0.26(17) ?
C7 N1 C8 C9 . . . . 178.60(11) ?
N1 C8 C9 C10 . . . . -178.90(12) ?
C17 C8 C9 C10 . . . . 0.01(19) ?
C8 C9 C10 C11 . . . . -0.6(2) ?
C9 C10 C11 O1 . . . . 179.92(13) ?
C9 C10 C11 C12 . . . . 1.0(2) ?
O1 C11 C12 C13 . . . . -1.6(2) ?
C10 C11 C12 C13 . . . . 177.40(12) ?
O1 C11 C12 C17 . . . . -179.71(12) ?
C10 C11 C12 C17 . . . . -0.76(17) ?
C17 C12 C13 C14 . . . . -0.32(19) ?
C11 C12 C13 C14 . . . . -178.48(12) ?
C12 C13 C14 C15 . . . . 0.4(2) ?
C13 C14 C15 C16 . . . . -0.3(2) ?
C7 N2 C16 C17 . . . . 0.73(17) ?
C7 N2 C16 C15 . . . . -178.36(11) ?
C14 C15 C16 N2 . . . . 179.33(12) ?
C14 C15 C16 C17 . . . . 0.24(19) ?
N2 C16 C17 C12 . . . . -179.29(10) ?
C15 C16 C17 C12 . . . . -0.20(18) ?
N2 C16 C17 C8 . . . . -0.99(17) ?
C15 C16 C17 C8 . . . . 178.10(11) ?
C13 C12 C17 C16 . . . . 0.24(18) ?
C11 C12 C17 C16 . . . . 178.45(10) ?
C13 C12 C17 C8 . . . . -177.98(11) ?
C11 C12 C17 C8 . . . . 0.23(18) ?
N1 C8 C17 C16 . . . . 0.77(17) ?
C9 C8 C17 C16 . . . . -178.10(11) ?
N1 C8 C17 C12 . . . . 179.04(11) ?
C9 C8 C17 C12 . . . . 0.17(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656553
2 PubChem 139080761
