#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/26/2222627.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_2222627
loop_
_publ_author_name
'Thenmozhi, M.'
'Kavitha, T.'
'Satyanarayana, V. S. V.'
'Vijayakumar, V.'
'Ponnuswamy, M. N.'
_publ_section_title
;Methyl
 4-(3-ethoxy-4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
 monohydrate
;
_journal_coeditor_code           CI2843
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1921
_journal_page_last               o1922
_journal_paper_doi               10.1107/S160053680902769X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H18 N2 O5, H2 O'
_chemical_formula_moiety         'C15 H18 N2 O5, H2 O'
_chemical_formula_sum            'C15 H20 N2 O6'
_chemical_formula_weight         324.33
_chemical_name_systematic
'Methyl 4-(3-ethoxy-4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate monohydrate'
_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                 95.932(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4927(6)
_cell_length_b                   15.3756(8)
_cell_length_c                   8.9240(5)
_cell_measurement_reflns_used    4719
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3
_cell_measurement_theta_min      1.8
_cell_volume                     1568.49(15)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII 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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20671
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.33
_diffrn_reflns_theta_min         1.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0476
_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)+(0.0643P)²+0.381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                3292
_reflns_number_total             4719
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2843.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222627
_cod_database_fobs_code          2222627
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_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
C C2 0.35042(12) 0.17029(9) 0.52062(17) 0.0356(3) Uani d . 1 . .
C C4 0.30165(12) 0.07826(8) 0.29487(15) 0.0323(3) Uani d . 1 . .
H H4 0.3447 0.0720 0.2063 0.039 Uiso calc R 1 . .
C C5 0.33233(11) 0.00144(8) 0.39770(15) 0.0318(3) Uani d . 1 . .
C C6 0.35124(11) 0.01266(8) 0.54780(16) 0.0321(3) Uani d . 1 . .
C C7 0.17205(12) 0.08179(8) 0.24074(15) 0.0314(3) Uani d . 1 . .
C C8 0.08815(12) 0.06691(10) 0.33778(15) 0.0372(3) Uani d . 1 . .
H H8 0.1109 0.0543 0.4385 0.045 Uiso calc R 1 . .
C C9 -0.02997(13) 0.07060(10) 0.28638(16) 0.0394(3) Uani d . 1 . .
H H9 -0.0858 0.0606 0.3528 0.047 Uiso calc R 1 . .
C C10 -0.06474(12) 0.08894(9) 0.13824(15) 0.0347(3) Uani d . 1 . .
C C11 0.01924(12) 0.10656(9) 0.03979(15) 0.0329(3) Uani d . 1 . .
C C12 0.13663(12) 0.10213(9) 0.09088(15) 0.0337(3) Uani d . 1 . .
H H12 0.1925 0.1128 0.0248 0.040 Uiso calc R 1 . .
C C13 0.05268(15) 0.15592(11) -0.20597(17) 0.0458(4) Uani d . 1 . .
H H13A 0.1074 0.1099 -0.2233 0.055 Uiso calc R 1 . .
H H13B 0.0966 0.2062 -0.1664 0.055 Uiso calc R 1 . .
C C14 -0.01997(19) 0.17865(13) -0.34907(19) 0.0579(5) Uani d . 1 . .
H H14A -0.0642 0.1287 -0.3857 0.087 Uiso calc R 1 . .
H H14B 0.0301 0.1968 -0.4229 0.087 Uiso calc R 1 . .
H H14C -0.0725 0.2251 -0.3306 0.087 Uiso calc R 1 . .
C C15 0.33489(12) -0.08120(9) 0.31629(17) 0.0373(3) Uani d . 1 . .
C C16 0.3448(2) -0.23424(11) 0.3223(3) 0.0685(6) Uani d . 1 . .
H H16A 0.2807 -0.2358 0.2442 0.103 Uiso calc R 1 . .
H H16B 0.3372 -0.2813 0.3913 0.103 Uiso calc R 1 . .
H H16C 0.4172 -0.2400 0.2783 0.103 Uiso calc R 1 . .
C C17 0.37615(14) -0.05489(10) 0.66793(17) 0.0422(3) Uani d . 1 . .
H H17A 0.3058 -0.0866 0.6803 0.063 Uiso calc R 1 . .
H H17B 0.4037 -0.0271 0.7612 0.063 Uiso calc R 1 . .
H H17C 0.4348 -0.0942 0.6392 0.063 Uiso calc R 1 . .
N N1 0.34801(11) 0.09613(8) 0.60651(15) 0.0381(3) Uani d . 1 . .
N N3 0.34091(11) 0.15896(8) 0.37262(14) 0.0371(3) Uani d . 1 . .
O O1 0.36409(10) 0.24219(7) 0.58341(13) 0.0474(3) Uani d . 1 . .
O O2 -0.18113(9) 0.09133(9) 0.09076(14) 0.0498(3) Uani d . 1 . .
O O3 -0.02656(9) 0.12778(8) -0.10273(11) 0.0444(3) Uani d . 1 . .
O O4 0.34354(12) -0.15218(7) 0.40215(14) 0.0555(3) Uani d . 1 . .
O O5 0.32921(11) -0.08496(8) 0.18008(13) 0.0521(3) Uani d . 1 . .
O O6 0.43101(15) 0.11524(11) 0.92163(16) 0.0654(4) Uani d . 1 . .
H H1 0.3666(16) 0.1039(11) 0.703(2) 0.045(5) Uiso d . 1 . .
H H2 -0.193(2) 0.0937(15) -0.010(3) 0.077(7) Uiso d . 1 . .
H H3 0.3418(15) 0.2040(12) 0.317(2) 0.048(5) Uiso d . 1 . .
H H6A 0.418(2) 0.1623(17) 0.981(3) 0.086(8) Uiso d . 1 . .
H H6B 0.508(3) 0.109(2) 0.921(4) 0.136(13) 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
O1 C2 N3 . . 124.06(13) ?
O1 C2 N1 . . 119.69(14) ?
N3 C2 N1 . . 116.23(12) ?
N3 C4 C5 . . 109.36(11) ?
N3 C4 C7 . . 111.30(11) ?
C5 C4 C7 . . 112.32(11) ?
N3 C4 H4 . . 107.9 ?
C5 C4 H4 . . 107.9 ?
C7 C4 H4 . . 107.9 ?
C6 C5 C15 . . 126.53(12) ?
C6 C5 C4 . . 120.43(12) ?
C15 C5 C4 . . 113.02(12) ?
C5 C6 N1 . . 119.10(12) ?
C5 C6 C17 . . 128.48(13) ?
N1 C6 C17 . . 112.41(12) ?
C8 C7 C12 . . 119.08(12) ?
C8 C7 C4 . . 121.36(12) ?
C12 C7 C4 . . 119.55(12) ?
C7 C8 C9 . . 120.57(13) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C10 C9 C8 . . 120.32(13) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
O2 C10 C9 . . 119.01(13) ?
O2 C10 C11 . . 121.30(12) ?
C9 C10 C11 . . 119.67(13) ?
O3 C11 C12 . . 126.10(12) ?
O3 C11 C10 . . 114.04(12) ?
C12 C11 C10 . . 119.86(12) ?
C11 C12 C7 . . 120.46(12) ?
C11 C12 H12 . . 119.8 ?
C7 C12 H12 . . 119.8 ?
O3 C13 C14 . . 106.57(14) ?
O3 C13 H13A . . 110.4 ?
C14 C13 H13A . . 110.4 ?
O3 C13 H13B . . 110.4 ?
C14 C13 H13B . . 110.4 ?
H13A C13 H13B . . 108.6 ?
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 ?
O5 C15 O4 . . 122.09(13) ?
O5 C15 C5 . . 122.48(13) ?
O4 C15 C5 . . 115.44(13) ?
O4 C16 H16A . . 109.5 ?
O4 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O4 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C6 C17 H17A . . 109.5 ?
C6 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C6 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C2 N1 C6 . . 123.58(13) ?
C2 N1 H1 . . 114.8(12) ?
C6 N1 H1 . . 119.0(12) ?
C2 N3 C4 . . 124.82(12) ?
C2 N3 H3 . . 118.0(12) ?
C4 N3 H3 . . 115.6(12) ?
C10 O2 H2 . . 111.0(15) ?
C11 O3 C13 . . 117.61(12) ?
C15 O4 C16 . . 115.74(14) ?
H6A O6 H6B . . 108(3) ?
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
C2 O1 . 1.2421(16) ?
C2 N3 . 1.3255(19) ?
C2 N1 . 1.3758(18) ?
C4 N3 . 1.4696(17) ?
C4 C5 . 1.5149(18) ?
C4 C7 . 1.5186(18) ?
C4 H4 . 0.98 ?
C5 C6 . 1.3457(19) ?
C5 C15 . 1.4654(19) ?
C6 N1 . 1.3881(18) ?
C6 C17 . 1.4988(19) ?
C7 C8 . 1.3801(19) ?
C7 C12 . 1.3926(18) ?
C8 C9 . 1.388(2) ?
C8 H8 . 0.93 ?
C9 C10 . 1.370(2) ?
C9 H9 . 0.93 ?
C10 O2 . 1.3613(17) ?
C10 C11 . 1.3972(19) ?
C11 O3 . 1.3648(16) ?
C11 C12 . 1.3804(19) ?
C12 H12 . 0.93 ?
C13 O3 . 1.4279(19) ?
C13 C14 . 1.493(2) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 O5 . 1.2119(18) ?
C15 O4 . 1.3314(18) ?
C16 O4 . 1.450(2) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
N1 H1 . 0.877(19) ?
N3 H3 . 0.852(19) ?
O2 H2 . 0.90(2) ?
O6 H6A . 0.92(3) ?
O6 H6B . 0.89(4) ?
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 O6 . 0.87(2) 2.02(2) 2.890(2) 172(2)
N3 H3 O1 4_565 0.85(2) 2.28(2) 3.031(2) 147(2)
O2 H2 O5 3 0.90(2) 2.07(2) 2.810(2) 139(2)
O6 H6A O1 4_566 0.92(3) 1.87(3) 2.777(2) 170(2)
O6 H6B O5 3_656 0.89(3) 2.19(3) 3.025(2) 156(3)
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
N3 C4 C5 C6 . . . . 21.65(17) ?
C7 C4 C5 C6 . . . . -102.44(14) ?
N3 C4 C5 C15 . . . . -159.91(11) ?
C7 C4 C5 C15 . . . . 76.00(14) ?
C15 C5 C6 N1 . . . . 178.59(12) ?
C4 C5 C6 N1 . . . . -3.19(19) ?
C15 C5 C6 C17 . . . . -1.7(2) ?
C4 C5 C6 C17 . . . . 176.53(13) ?
N3 C4 C7 C8 . . . . -79.50(16) ?
C5 C4 C7 C8 . . . . 43.50(17) ?
N3 C4 C7 C12 . . . . 99.20(14) ?
C5 C4 C7 C12 . . . . -137.80(13) ?
C12 C7 C8 C9 . . . . 1.1(2) ?
C4 C7 C8 C9 . . . . 179.85(13) ?
C7 C8 C9 C10 . . . . 0.1(2) ?
C8 C9 C10 O2 . . . . 179.40(14) ?
C8 C9 C10 C11 . . . . -1.9(2) ?
O2 C10 C11 O3 . . . . 1.5(2) ?
C9 C10 C11 O3 . . . . -177.11(13) ?
O2 C10 C11 C12 . . . . -178.89(13) ?
C9 C10 C11 C12 . . . . 2.5(2) ?
O3 C11 C12 C7 . . . . 178.32(13) ?
C10 C11 C12 C7 . . . . -1.2(2) ?
C8 C7 C12 C11 . . . . -0.6(2) ?
C4 C7 C12 C11 . . . . -179.32(12) ?
C6 C5 C15 O5 . . . . -171.98(14) ?
C4 C5 C15 O5 . . . . 9.7(2) ?
C6 C5 C15 O4 . . . . 8.2(2) ?
C4 C5 C15 O4 . . . . -170.10(12) ?
O1 C2 N1 C6 . . . . -169.74(13) ?
N3 C2 N1 C6 . . . . 8.4(2) ?
C5 C6 N1 C2 . . . . -13.8(2) ?
C17 C6 N1 C2 . . . . 166.38(13) ?
O1 C2 N3 C4 . . . . -167.13(14) ?
N1 C2 N3 C4 . . . . 14.8(2) ?
C5 C4 N3 C2 . . . . -28.53(18) ?
C7 C4 N3 C2 . . . . 96.16(15) ?
C12 C11 O3 C13 . . . . -6.2(2) ?
C10 C11 O3 C13 . . . . 173.34(13) ?
C14 C13 O3 C11 . . . . -177.41(13) ?
O5 C15 O4 C16 . . . . -0.5(2) ?
C5 C15 O4 C16 . . . . 179.32(14) ?
