#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/92/2219257.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_2219257
loop_
_publ_author_name
'Nizam Mohideen, M.'
'Rasheeth, A.'
'Huq, C. A. M. A.'
'Nizar, S. Syed'
_publ_section_title
;
 Ethyl
 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
;
_journal_coeditor_code           BT2758
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1752
_journal_paper_doi               10.1107/S1600536808025610
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H16 N2 O3'
_chemical_formula_moiety         'C14 H16 N2 O3'
_chemical_formula_sum            'C14 H16 N2 O3'
_chemical_formula_weight         260.29
_chemical_name_systematic
;
Ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.843(2)
_cell_angle_beta                 108.6030(10)
_cell_angle_gamma                98.244(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5495(2)
_cell_length_b                   8.9797(3)
_cell_length_c                   11.0812(3)
_cell_measurement_reflns_used    5321
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1
_cell_measurement_theta_min      2.5
_cell_volume                     653.07(4)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and 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 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
Bruker APEXII CCD area-detector
;
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16135
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.73
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.326
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0959P)²+0.106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1589
_reflns_number_gt                2972
_reflns_number_total             3710
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2758.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'None' changed to 'none' 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:

'_exptl_absorpt_correction_type' value 'None' changed to 'none'
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-1
_cod_database_code               2219257
_cod_database_fobs_code          2219257
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 -0.18468(12) 0.90274(12) 0.54481(10) 0.0472(2) Uani d . 1
O O2 0.51966(14) 0.59340(12) 0.67258(11) 0.0546(3) Uani d . 1
O O3 0.30937(13) 0.47104(11) 0.73822(10) 0.0473(2) Uani d . 1
N N1 -0.09885(13) 0.70875(12) 0.62494(10) 0.0389(2) Uani d . 1
H H1 -0.2165 0.6651 0.6107 0.047 Uiso calc R 1
N N2 0.10294(14) 0.85056(13) 0.55737(11) 0.0413(2) Uani d . 1
H H2 0.1288 0.9264 0.5285 0.050 Uiso calc R 1
C C1 0.2277(2) 0.89996(17) 0.91862(15) 0.0542(3) Uani d . 1
H H1A 0.2782 0.9495 0.8699 0.065 Uiso calc R 1
C C2 0.2660(3) 0.9866(2) 1.05616(17) 0.0711(5) Uani d . 1
H H2A 0.3398 1.0942 1.0982 0.085 Uiso calc R 1
C C3 0.1961(3) 0.9148(3) 1.12917(17) 0.0757(5) Uani d . 1
H H3 0.2226 0.9726 1.2212 0.091 Uiso calc R 1
C C4 0.0872(4) 0.7575(3) 1.0669(2) 0.0860(6) Uani d . 1
H H4 0.0400 0.7079 1.1170 0.103 Uiso calc R 1
C C5 0.0461(3) 0.6709(2) 0.93002(18) 0.0663(4) Uani d . 1
H H5 -0.0292 0.5638 0.8885 0.080 Uiso calc R 1
C C6 0.11595(16) 0.74226(14) 0.85451(12) 0.0380(2) Uani d . 1
C C7 0.05617(15) 0.65119(13) 0.70151(12) 0.0351(2) Uani d . 1
H H7 0.0032 0.5360 0.6808 0.042 Uiso calc R 1
C C8 -0.06779(16) 0.82505(14) 0.57613(12) 0.0363(2) Uani d . 1
C C9 0.23610(16) 0.76219(13) 0.58195(12) 0.0371(2) Uani d . 1
C C10 0.22084(15) 0.66550(13) 0.65175(11) 0.0353(2) Uani d . 1
C C11 0.3835(2) 0.7861(2) 0.52121(17) 0.0556(4) Uani d . 1
H H11A 0.5017 0.8612 0.5918 0.083 Uiso calc R 1
H H11B 0.3354 0.8286 0.4511 0.083 Uiso calc R 1
H H11C 0.4080 0.6839 0.4817 0.083 Uiso calc R 1
C C12 0.36538(16) 0.57600(13) 0.68571(12) 0.0387(2) Uani d . 1
C C13 0.4443(2) 0.37945(18) 0.77957(16) 0.0533(3) Uani d . 1
H H13A 0.5686 0.4526 0.8461 0.064 Uiso calc R 1
H H13B 0.4638 0.3116 0.7006 0.064 Uiso calc R 1
C C14 0.3605(3) 0.2774(2) 0.8412(2) 0.0736(5) Uani d . 1
H H14A 0.3373 0.3455 0.9171 0.110 Uiso calc R 1
H H14B 0.4495 0.2185 0.8729 0.110 Uiso calc R 1
H H14C 0.2403 0.2023 0.7733 0.110 Uiso calc R 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
C12 O3 C13 . 116.09(10)
C8 N1 C7 . 123.94(9)
C8 N1 H1 . 118.0
C7 N1 H1 . 118.0
C8 N2 C9 . 124.03(10)
C8 N2 H2 . 118.0
C9 N2 H2 . 118.0
C6 C1 C2 . 120.50(14)
C6 C1 H1A . 119.8
C2 C1 H1A . 119.8
C3 C2 C1 . 120.33(17)
C3 C2 H2A . 119.8
C1 C2 H2A . 119.8
C2 C3 C4 . 119.62(15)
C2 C3 H3 . 120.2
C4 C3 H3 . 120.2
C3 C4 C5 . 120.60(17)
C3 C4 H4 . 119.7
C5 C4 H4 . 119.7
C6 C5 C4 . 120.44(17)
C6 C5 H5 . 119.8
C4 C5 H5 . 119.8
C1 C6 C5 . 118.50(13)
C1 C6 C7 . 121.28(11)
C5 C6 C7 . 120.04(12)
N1 C7 C10 . 109.36(9)
N1 C7 C6 . 109.37(9)
C10 C7 C6 . 114.22(9)
N1 C7 H7 . 107.9
C10 C7 H7 . 107.9
C6 C7 H7 . 107.9
O1 C8 N1 . 123.84(10)
O1 C8 N2 . 120.40(10)
N1 C8 N2 . 115.72(10)
C10 C9 N2 . 119.72(10)
C10 C9 C11 . 127.49(11)
N2 C9 C11 . 112.77(10)
C9 C10 C12 . 121.18(10)
C9 C10 C7 . 120.31(10)
C12 C10 C7 . 118.47(10)
C9 C11 H11A . 109.5
C9 C11 H11B . 109.5
H11A C11 H11B . 109.5
C9 C11 H11C . 109.5
H11A C11 H11C . 109.5
H11B C11 H11C . 109.5
O2 C12 O3 1 122.18(11)
O2 C12 O3 . 122.18(11)
O2 C12 C10 1 126.44(11)
O2 C12 C10 . 126.44(11)
O3 C12 C10 . 111.36(9)
O3 C13 C14 . 107.69(12)
O3 C13 H13A . 110.2
C14 C13 H13A . 110.2
O3 C13 H13B . 110.2
C14 C13 H13B . 110.2
H13A C13 H13B . 108.5
C13 C14 H14A . 109.5
C13 C14 H14B . 109.5
H14A C14 H14B . 109.5
C13 C14 H14C . 109.5
H14A C14 H14C . 109.5
H14B C14 H14C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C8 . 1.2310(14)
O2 C12 . 1.2133(14)
O3 C12 . 1.3359(15)
O3 C13 . 1.4481(15)
N1 C8 . 1.3398(15)
N1 C7 . 1.4716(15)
N1 H1 . 0.8600
N2 C8 . 1.3684(14)
N2 C9 . 1.3788(14)
N2 H2 . 0.8600
C1 C6 . 1.3712(18)
C1 C2 . 1.393(2)
C1 H1A . 0.9300
C2 C3 . 1.357(3)
C2 H2A . 0.9300
C3 C4 . 1.362(3)
C3 H3 . 0.9300
C4 C5 . 1.382(3)
C4 H4 . 0.9300
C5 C6 . 1.3793(18)
C5 H5 . 0.9300
C6 C7 . 1.5176(16)
C7 C10 . 1.5168(14)
C7 H7 . 0.9800
C9 C10 . 1.3436(16)
C9 C11 . 1.4950(15)
C10 C12 . 1.4673(15)
C11 H11A . 0.9600
C11 H11B . 0.9600
C11 H11C . 0.9600
C12 O2 1 1.2133(14)
C13 C14 . 1.483(2)
C13 H13A . 0.9700
C13 H13B . 0.9700
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
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
N1 H1 O2 1_455 0.86 2.37 3.1773(13) 156.0
N2 H2 O1 2_576 0.86 2.00 2.8568(13) 178.2
C11 H11A O1 1_655 0.96 2.58 3.1785(16) 120.5
C11 H11C O2 1 0.96 2.44 2.8379(17) 104.5
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_4
_geom_torsion
C6 C1 C2 C3 . 1.3(3)
C1 C2 C3 C4 . -0.4(3)
C2 C3 C4 C5 . -0.4(3)
C3 C4 C5 C6 . 0.4(3)
C2 C1 C6 C5 . -1.3(2)
C2 C1 C6 C7 . 173.94(13)
C4 C5 C6 C1 . 0.4(3)
C4 C5 C6 C7 . -174.83(16)
C8 N1 C7 C10 . -31.02(15)
C8 N1 C7 C6 . 94.75(12)
C1 C6 C7 N1 . -75.26(14)
C5 C6 C7 N1 . 99.89(14)
C1 C6 C7 C10 . 47.66(15)
C5 C6 C7 C10 . -137.19(13)
C7 N1 C8 O1 . -160.27(11)
C7 N1 C8 N2 . 22.03(16)
C9 N2 C8 O1 . -175.96(11)
C9 N2 C8 N1 . 1.82(17)
C8 N2 C9 C10 . -12.97(18)
C8 N2 C9 C11 . 165.78(12)
N2 C9 C10 C12 . -176.93(10)
C11 C9 C10 C12 . 4.52(19)
N2 C9 C10 C7 . 0.98(17)
C11 C9 C10 C7 . -177.57(12)
N1 C7 C10 C9 . 18.31(14)
C6 C7 C10 C9 . -104.61(12)
N1 C7 C10 C12 . -163.72(9)
C6 C7 C10 C12 . 73.35(12)
C13 O3 C12 O2 1 0.36(18)
C13 O3 C12 O2 . 0.36(18)
C13 O3 C12 C10 . -178.13(10)
C9 C10 C12 O2 1 10.07(19)
C7 C10 C12 O2 1 -167.88(12)
C9 C10 C12 O2 . 10.07(19)
C7 C10 C12 O2 . -167.88(12)
C9 C10 C12 O3 . -171.52(10)
C7 C10 C12 O3 . 10.53(14)
C12 O3 C13 C14 . 177.11(13)
