#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/05/2220505.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_2220505
loop_
_publ_author_name
'Chitra, S.'
'Pandiarajan, K.'
'Anuradha, N.'
'Thiruvalluvar, A.'
_publ_section_title
;
 5-Acetyl-4-(4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one
;
_journal_coeditor_code           HB2869
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o23
_journal_paper_doi               10.1107/S1600536808040270
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H16 N2 O3'
_chemical_formula_moiety         'C14 H16 N2 O3'
_chemical_formula_structural     'C14 H16 N2 O3'
_chemical_formula_sum            'C14 H16 N2 O3'
_chemical_formula_weight         260.29
_chemical_melting_point          474.5
_chemical_name_common            Dihydropyrimidinone
_chemical_name_systematic
;
5-Acetyl-4-(4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-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
_cell_angle_alpha                90
_cell_angle_beta                 108.305(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.7948(12)
_cell_length_b                   7.9905(3)
_cell_length_c                   14.4757(7)
_cell_measurement_reflns_used    5096
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.346
_cell_measurement_theta_min      2.688
_cell_volume                     2613.0(2)
_computing_cell_refinement       'SAINT-NT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-NT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26518
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0771P)²+1.0144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1492
_reflns_number_gt                2226
_reflns_number_total             2960
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2869.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2220505
_cod_database_fobs_code          2220505
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O2 0.03463(6) 0.62339(16) -0.06612(9) 0.0448(4) Uani d . 1.000
O O15 0.06948(6) 0.98745(15) 0.31847(8) 0.0430(4) Uani d . 1.000
O O44 0.27417(7) 0.4726(2) 0.44596(12) 0.0748(6) Uani d . 1.000
N N1 0.07453(7) 0.86574(18) 0.00570(10) 0.0358(4) Uani d . 1.000
N N3 0.04449(7) 0.66399(18) 0.09271(10) 0.0351(4) Uani d . 1.000
C C2 0.05037(7) 0.7104(2) 0.00812(11) 0.0319(5) Uani d . 1.000
C C4 0.06651(7) 0.75657(19) 0.18405(11) 0.0297(4) Uani d . 1.000
C C5 0.07616(7) 0.93953(19) 0.16471(11) 0.0294(5) Uani d . 1.000
C C6 0.08211(7) 0.98438(19) 0.07810(11) 0.0303(5) Uani d . 1.000
C C14 0.27926(12) 0.4564(4) 0.54607(19) 0.0879(11) Uani d . 1.000
C C15 0.07743(7) 1.0494(2) 0.24592(11) 0.0332(5) Uani d . 1.000
C C16 0.08710(11) 1.2339(2) 0.24595(14) 0.0558(7) Uani d . 1.000
C C41 0.12158(7) 0.67712(19) 0.25352(11) 0.0320(5) Uani d . 1.000
C C42 0.17355(9) 0.6594(3) 0.23045(14) 0.0514(7) Uani d . 1.000
C C43 0.22307(10) 0.5896(3) 0.29545(17) 0.0624(8) Uani d . 1.000
C C44 0.22238(9) 0.5391(3) 0.38624(14) 0.0493(6) Uani d . 1.000
C C45 0.17137(9) 0.5551(2) 0.41034(13) 0.0436(6) Uani d . 1.000
C C46 0.12122(8) 0.6231(2) 0.34341(12) 0.0362(5) Uani d . 1.000
C C61 0.09756(9) 1.1526(2) 0.04681(13) 0.0424(6) Uani d . 1.000
H H1 0.0736(9) 0.901(3) -0.0548(16) 0.048(6) Uiso d . 1.000
H H3 0.0231(9) 0.572(3) 0.0913(14) 0.046(6) Uiso d . 1.000
H H4 0.03559 0.75256 0.21553 0.0356 Uiso calc R 1.000
H H14A 0.27276 0.56325 0.57124 0.1316 Uiso calc R 1.000
H H14B 0.31818 0.41685 0.58148 0.1316 Uiso calc R 1.000
H H14C 0.25029 0.37800 0.55309 0.1316 Uiso calc R 1.000
H H16A 0.08324 1.28140 0.30456 0.0837 Uiso calc R 1.000
H H16B 0.05821 1.28296 0.19064 0.0837 Uiso calc R 1.000
H H16C 0.12608 1.25601 0.24265 0.0837 Uiso calc R 1.000
H H42 0.17493 0.69534 0.17010 0.0616 Uiso calc R 1.000
H H43 0.25728 0.57630 0.27812 0.0749 Uiso calc R 1.000
H H45 0.17030 0.52054 0.47112 0.0523 Uiso calc R 1.000
H H46 0.08658 0.63227 0.35988 0.0434 Uiso calc R 1.000
H H61A 0.06570 1.22943 0.04172 0.0636 Uiso calc R 1.000
H H61B 0.10388 1.14266 -0.01528 0.0636 Uiso calc R 1.000
H H61C 0.13299 1.19346 0.09397 0.0636 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O44 C44 . . . 116.75(19) no
C2 N1 C6 . . . 123.82(14) no
C2 N3 C4 . . . 125.54(14) no
C2 N1 H1 . . . 114.8(15) no
C6 N1 H1 . . . 118.3(15) no
C2 N3 H3 . . . 115.7(13) no
C4 N3 H3 . . . 118.6(13) no
O2 C2 N3 . . . 123.64(16) no
N1 C2 N3 . . . 116.24(14) no
O2 C2 N1 . . . 120.11(15) no
N3 C4 C5 . . . 110.63(13) no
N3 C4 C41 . . . 112.17(13) no
C5 C4 C41 . . . 112.06(13) no
C4 C5 C15 . . . 113.35(13) no
C6 C5 C15 . . . 127.23(14) no
C4 C5 C6 . . . 119.42(14) no
N1 C6 C5 . . . 119.61(14) no
N1 C6 C61 . . . 111.81(14) no
C5 C6 C61 . . . 128.58(14) no
C5 C15 C16 . . . 123.96(15) no
O15 C15 C5 . . . 118.45(14) no
O15 C15 C16 . . . 117.59(15) no
C4 C41 C46 . . . 119.88(16) no
C42 C41 C46 . . . 117.89(16) no
C4 C41 C42 . . . 122.22(15) no
C41 C42 C43 . . . 120.97(19) no
C42 C43 C44 . . . 120.4(2) no
O44 C44 C43 . . . 115.9(2) no
C43 C44 C45 . . . 119.5(2) no
O44 C44 C45 . . . 124.64(18) no
C44 C45 C46 . . . 119.62(17) no
C41 C46 C45 . . . 121.59(18) no
N3 C4 H4 . . . 107.00 no
C5 C4 H4 . . . 107.00 no
C41 C4 H4 . . . 107.00 no
O44 C14 H14A . . . 109.00 no
O44 C14 H14B . . . 109.00 no
O44 C14 H14C . . . 109.00 no
H14A C14 H14B . . . 109.00 no
H14A C14 H14C . . . 109.00 no
H14B C14 H14C . . . 109.00 no
C15 C16 H16A . . . 109.00 no
C15 C16 H16B . . . 109.00 no
C15 C16 H16C . . . 109.00 no
H16A C16 H16B . . . 109.00 no
H16A C16 H16C . . . 109.00 no
H16B C16 H16C . . . 109.00 no
C41 C42 H42 . . . 119.00 no
C43 C42 H42 . . . 120.00 no
C42 C43 H43 . . . 120.00 no
C44 C43 H43 . . . 120.00 no
C44 C45 H45 . . . 120.00 no
C46 C45 H45 . . . 120.00 no
C41 C46 H46 . . . 119.00 no
C45 C46 H46 . . . 119.00 no
C6 C61 H61A . . . 109.00 no
C6 C61 H61B . . . 109.00 no
C6 C61 H61C . . . 109.00 no
H61A C61 H61B . . . 109.00 no
H61A C61 H61C . . . 109.00 no
H61B C61 H61C . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C2 . . 1.235(2) no
O15 C15 . . 1.228(2) no
O44 C14 . . 1.422(3) no
O44 C44 . . 1.371(3) no
N1 C2 . . 1.373(2) no
N1 C6 . . 1.382(2) no
N3 C2 . . 1.328(2) no
N3 C4 . . 1.461(2) no
N1 H1 . . 0.91(2) no
N3 H3 . . 0.89(2) no
C4 C41 . . 1.518(2) no
C4 C5 . . 1.520(2) no
C5 C6 . . 1.354(2) no
C5 C15 . . 1.460(2) no
C6 C61 . . 1.501(2) no
C15 C16 . . 1.492(2) no
C41 C46 . . 1.374(2) no
C41 C42 . . 1.386(3) no
C42 C43 . . 1.374(3) no
C43 C44 . . 1.380(3) no
C44 C45 . . 1.370(3) no
C45 C46 . . 1.390(3) no
C4 H4 . . 0.9800 no
C14 H14A . . 0.9600 no
C14 H14B . . 0.9600 no
C14 H14C . . 0.9600 no
C16 H16A . . 0.9600 no
C16 H16B . . 0.9600 no
C16 H16C . . 0.9600 no
C42 H42 . . 0.9300 no
C43 H43 . . 0.9300 no
C45 H45 . . 0.9300 no
C46 H46 . . 0.9300 no
C61 H61A . . 0.9600 no
C61 H61B . . 0.9600 no
C61 H61C . . 0.9600 no
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
N1 H1 O15 4_574 0.91(2) 2.01(2) 2.9209(18) 172(2) yes
N3 H3 O2 3_565 0.89(2) 2.04(2) 2.917(2) 170.3(19) yes
C16 H16B O2 3_575 0.96 2.49 3.425(3) 165 yes
C61 H61B O15 4_574 0.96 2.51 3.352(2) 146 yes
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
C14 O44 C44 C43 . . . . 165.7(2) no
C14 O44 C44 C45 . . . . -15.5(3) no
C6 N1 C2 O2 . . . . 166.26(17) no
C6 N1 C2 N3 . . . . -12.6(3) no
C2 N1 C6 C5 . . . . 12.8(3) no
C2 N1 C6 C61 . . . . -168.20(17) no
C4 N3 C2 O2 . . . . 174.99(17) no
C4 N3 C2 N1 . . . . -6.2(3) no
C2 N3 C4 C5 . . . . 21.4(2) no
C2 N3 C4 C41 . . . . -104.54(19) no
N3 C4 C5 C6 . . . . -20.2(2) no
N3 C4 C5 C15 . . . . 159.41(15) no
C41 C4 C5 C6 . . . . 105.84(17) no
C41 C4 C5 C15 . . . . -74.59(18) no
N3 C4 C41 C42 . . . . 61.2(2) no
N3 C4 C41 C46 . . . . -120.13(16) no
C5 C4 C41 C42 . . . . -64.0(2) no
C5 C4 C41 C46 . . . . 114.72(17) no
C4 C5 C6 N1 . . . . 5.3(3) no
C4 C5 C6 C61 . . . . -173.60(17) no
C15 C5 C6 N1 . . . . -174.25(17) no
C15 C5 C6 C61 . . . . 6.9(3) no
C4 C5 C15 O15 . . . . -1.7(2) no
C4 C5 C15 C16 . . . . 179.10(18) no
C6 C5 C15 O15 . . . . 177.84(18) no
C6 C5 C15 C16 . . . . -1.4(3) no
C4 C41 C42 C43 . . . . 178.86(19) no
C46 C41 C42 C43 . . . . 0.2(3) no
C4 C41 C46 C45 . . . . -177.71(15) no
C42 C41 C46 C45 . . . . 1.0(3) no
C41 C42 C43 C44 . . . . -1.5(4) no
C42 C43 C44 O44 . . . . -179.4(2) no
C42 C43 C44 C45 . . . . 1.7(3) no
O44 C44 C45 C46 . . . . -179.37(19) no
C43 C44 C45 C46 . . . . -0.5(3) no
C44 C45 C46 C41 . . . . -0.9(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2096544
