#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/01/2210184.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_2210184
loop_
_publ_author_name
'Victor B. Rybakov'
'Vadim L. Alifanov'
'Pavel V. Gormay'
'Eugene V. Babaev'
_publ_section_title
;
 1-[(4-Chlorobenzoyl)methyl]-4,6-dimethyl-2(1H)-pyrimidone
;
_journal_coeditor_code           CV2083
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3840
_journal_page_last               o3841
_journal_paper_doi               10.1107/S1600536806031199
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H13 Cl N2 O2'
_chemical_formula_moiety         'C14 H13 Cl N2 O2'
_chemical_formula_sum            'C14 H13 Cl N2 O2'
_chemical_formula_weight         276.71
_chemical_melting_point          446
_chemical_name_systematic
;
1-[(4-Chlorobenzoyl)methyl]-4,6-dimethyl-2(1H)-pyrimidone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.314(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1975(8)
_cell_length_b                   9.3817(10)
_cell_length_c                   19.422(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33
_cell_measurement_theta_min      30
_cell_volume                     1310.4(3)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS'
_computing_data_reduction        'XCAD4 (Harms & Wokadlo, (1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2760
_diffrn_reflns_theta_full        74.86
_diffrn_reflns_theta_max         74.86
_diffrn_reflns_theta_min         4.56
_diffrn_standards_decay_%        4
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    2.583
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0422P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0859
_reflns_number_gt                1907
_reflns_number_total             2683
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2083.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210184
_cod_database_fobs_code          2210184
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N N1 0.06506(16) 0.44796(13) 0.72057(6) 0.0447(3) Uani d . 1
C C2 0.0976(2) 0.54726(17) 0.66780(8) 0.0525(4) Uani d . 1
O O2 0.24693(18) 0.60918(14) 0.66857(7) 0.0749(4) Uani d . 1
N N3 -0.0403(2) 0.57024(15) 0.61881(7) 0.0588(4) Uani d . 1
C C4 -0.1962(2) 0.49939(18) 0.62188(8) 0.0543(4) Uani d . 1
C C41 -0.3433(3) 0.5293(3) 0.56670(10) 0.0871(7) Uani d . 1
H H41A -0.3350 0.6270 0.5525 0.131 Uiso calc R 1
H H41B -0.4638 0.5118 0.5844 0.131 Uiso calc R 1
H H41C -0.3251 0.4681 0.5279 0.131 Uiso calc R 1
C C5 -0.2315(2) 0.39954(17) 0.67347(9) 0.0544(4) Uani d . 1
H H5 -0.3440 0.3508 0.6734 0.065 Uiso calc R 1
C C6 -0.0981(2) 0.37535(16) 0.72360(8) 0.0460(3) Uani d . 1
C C61 -0.1249(2) 0.2720(2) 0.78081(10) 0.0645(5) Uani d . 1
H H61A -0.2454 0.2289 0.7752 0.097 Uiso calc R 1
H H61B -0.1155 0.3213 0.8241 0.097 Uiso calc R 1
H H61C -0.0309 0.1995 0.7798 0.097 Uiso calc R 1
C C7 0.2147(2) 0.43830(17) 0.77377(8) 0.0505(4) Uani d . 1
H H7A 0.3338 0.4357 0.7522 0.061 Uiso calc R 1
H H7B 0.2015 0.3507 0.7997 0.061 Uiso calc R 1
C C8 0.2092(2) 0.56504(18) 0.82245(8) 0.0494(4) Uani d . 1
O O8 0.07713(17) 0.64427(14) 0.82093(7) 0.0755(4) Uani d . 1
C C9 0.3723(2) 0.58649(16) 0.87126(7) 0.0460(3) Uani d . 1
C C10 0.5266(2) 0.5011(2) 0.87179(9) 0.0658(5) Uani d . 1
H H10 0.5316 0.4254 0.8410 0.079 Uiso calc R 1
C C11 0.6757(2) 0.5261(2) 0.91776(10) 0.0695(5) Uani d . 1
H H11 0.7813 0.4691 0.9172 0.083 Uiso calc R 1
C C12 0.6654(2) 0.63622(19) 0.96415(8) 0.0537(4) Uani d . 1
C C13 0.5112(2) 0.7211(2) 0.96540(9) 0.0614(4) Uani d . 1
H H13 0.5053 0.7948 0.9973 0.074 Uiso calc R 1
C C14 0.3639(2) 0.69656(19) 0.91894(8) 0.0564(4) Uani d . 1
H H14 0.2587 0.7540 0.9196 0.068 Uiso calc R 1
Cl Cl12 0.85163(7) 0.66768(6) 1.02110(3) 0.07873(18) Uani 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 1 3
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
C6 N1 C2 122.06(12) y
C6 N1 C7 123.33(13) y
C2 N1 C7 114.45(12) y
O2 C2 N3 123.27(16) y
O2 C2 N1 118.50(14) y
N3 C2 N1 118.23(14) y
C4 N3 C2 119.31(15) y
N3 C4 C5 123.56(14) y
N3 C4 C41 116.99(17) n
C5 C4 C41 119.45(16) n
C4 C41 H41A 109.5 n
C4 C41 H41B 109.5 n
H41A C41 H41B 109.5 n
C4 C41 H41C 109.5 n
H41A C41 H41C 109.5 n
H41B C41 H41C 109.5 n
C6 C5 C4 118.71(15) y
C6 C5 H5 120.6 n
C4 C5 H5 120.6 n
C5 C6 N1 118.13(15) y
C5 C6 C61 122.21(15) n
N1 C6 C61 119.66(13) n
C6 C61 H61A 109.5 n
C6 C61 H61B 109.5 n
H61A C61 H61B 109.5 n
C6 C61 H61C 109.5 n
H61A C61 H61C 109.5 n
H61B C61 H61C 109.5 n
N1 C7 C8 110.70(12) y
N1 C7 H7A 109.5 n
C8 C7 H7A 109.5 n
N1 C7 H7B 109.5 n
C8 C7 H7B 109.5 n
H7A C7 H7B 108.1 n
O8 C8 C9 122.09(15) n
O8 C8 C7 120.45(14) n
C9 C8 C7 117.45(13) n
C10 C9 C14 119.13(14) n
C10 C9 C8 122.87(14) n
C14 C9 C8 117.98(13) n
C9 C10 C11 120.76(17) n
C9 C10 H10 119.6 n
C11 C10 H10 119.6 n
C12 C11 C10 119.22(17) n
C12 C11 H11 120.4 n
C10 C11 H11 120.4 n
C13 C12 C11 120.97(14) n
C13 C12 Cl12 119.89(13) n
C11 C12 Cl12 119.14(13) n
C12 C13 C14 119.53(16) n
C12 C13 H13 120.2 n
C14 C13 H13 120.2 n
C13 C14 C9 120.36(16) n
C13 C14 H14 119.8 n
C9 C14 H14 119.8 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 1.3607(18) y
N1 C2 1.4116(19) y
N1 C7 1.4648(16) y
C2 O2 1.2210(18) y
C2 N3 1.3645(18) y
N3 C4 1.307(2) y
C4 C5 1.402(2) y
C4 C41 1.502(2) y
C41 H41A 0.9600 n
C41 H41B 0.9600 n
C41 H41C 0.9600 n
C5 C6 1.3586(19) y
C5 H5 0.9300 n
C6 C61 1.493(2) y
C61 H61A 0.9600 n
C61 H61B 0.9600 n
C61 H61C 0.9600 n
C7 C8 1.521(2) n
C7 H7A 0.9700 n
C7 H7B 0.9700 n
C8 O8 1.2061(18) n
C8 C9 1.4924(18) n
C9 C10 1.370(2) n
C9 C14 1.390(2) n
C10 C11 1.388(2) n
C10 H10 0.9300 n
C11 C12 1.374(2) n
C11 H11 0.9300 n
C12 C13 1.367(2) n
C12 Cl12 1.7284(15) n
C13 C14 1.383(2) n
C13 H13 0.9300 n
C14 H14 0.9300 n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127532
