#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/73/2227361.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227361
loop_
_publ_author_name
'Wang, Hong-Yun'
_publ_section_title
;
 Ethyl
 4-(furan-2-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
;
_journal_coeditor_code           CV2771
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2822
_journal_paper_doi               10.1107/S1600536810040456
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H14 N2 O4'
_chemical_formula_moiety         'C12 H14 N2 O4'
_chemical_formula_sum            'C12 H14 N2 O4'
_chemical_formula_weight         250.25
_chemical_name_systematic
;
Ethyl 4-(furan-2-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
;
_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                 118.300(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.1720(14)
_cell_length_b                   13.3180(15)
_cell_length_c                   17.116(2)
_cell_measurement_reflns_used    1664
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.256
_cell_measurement_theta_min      2.304
_cell_volume                     2443.0(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0691
_diffrn_reflns_av_sigmaI/netI    0.0781
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11604
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_correction_T_min  0.9520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.1466
_refine_ls_R_factor_gt           0.0706
_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)+(0.1244P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1853
_refine_ls_wR_factor_ref         0.2370
_reflns_number_gt                1943
_reflns_number_total             4298
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv2771.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227361
_cod_database_fobs_code          2227361
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
N N1 0.0677(3) 0.8975(2) 0.4632(2) 0.0478(9) Uani d . 1 . .
H H1 0.0351 0.9555 0.4437 0.057 Uiso calc R 1 . .
N N2 0.0574(3) 0.7467(2) 0.5219(2) 0.0479(8) Uani d . 1 . .
H H2 0.0468 0.7135 0.5609 0.057 Uiso calc R 1 . .
N N3 0.8736(3) 0.6124(2) 0.7072(2) 0.0499(9) Uani d . 1 . .
H H3 0.8988 0.5511 0.7182 0.060 Uiso calc R 1 . .
N N4 0.8981(3) 0.7698(2) 0.6635(2) 0.0497(8) Uani d . 1 . .
H H4 0.9196 0.8075 0.6321 0.060 Uiso calc R 1 . .
O O1 -0.0199(2) 0.88634(18) 0.55364(19) 0.0574(8) Uani d . 1 . .
O O2 0.3239(6) 0.8613(5) 0.5879(5) 0.086(2) Uani d P 0.625(6) A 1
C C4' 0.3192(18) 0.9228(13) 0.5941(13) 0.086(2) Uani d P 0.375(6) A 2
H H4' 0.2672 0.9425 0.6173 0.103 Uiso calc PR 0.375(6) A 2
O O3 0.2203(2) 0.7669(2) 0.32562(17) 0.0565(8) Uani d . 1 . .
O O4 0.1728(3) 0.6108(2) 0.3447(2) 0.0686(9) Uani d . 1 . .
O O5 0.9657(3) 0.63333(18) 0.6200(2) 0.0600(8) Uani d . 1 . .
O O6 0.6054(4) 0.6411(3) 0.5976(3) 0.1107(13) Uani d . 1 . .
O O7 0.7327(3) 0.7358(2) 0.85737(19) 0.0690(9) Uani d . 1 . .
O O8 0.7471(3) 0.8936(2) 0.8223(2) 0.0780(10) Uani d . 1 . .
C C1 0.0329(3) 0.8474(3) 0.5145(3) 0.0456(10) Uani d . 1 . .
C C2 0.1585(3) 0.8589(3) 0.4384(3) 0.0429(10) Uani d . 1 A .
H H2A 0.1438 0.8907 0.3826 0.052 Uiso calc R 1 . .
C C3 0.2873(4) 0.8830(3) 0.5074(3) 0.0559(11) Uani d . 1 . .
C C4 0.3859(8) 0.9166(7) 0.4951(7) 0.079(2) Uani d P 0.625(6) A 1
H H4A 0.3852 0.9349 0.4424 0.094 Uiso calc PR 0.625(6) A 1
C C5 0.4870(15) 0.9164(9) 0.5815(12) 0.086(4) Uani d P 0.625(6) A 1
H H5 0.5680 0.9359 0.5966 0.103 Uiso calc PR 0.625(6) A 1
C C6 0.448(2) 0.8828(11) 0.6403(17) 0.091(4) Uani d P 0.625(6) A 1
H H6 0.4943 0.8764 0.7016 0.109 Uiso calc PR 0.625(6) A 1
O O2' 0.3875(9) 0.8450(8) 0.5162(7) 0.079(2) Uani d P 0.375(6) A 2
C C5' 0.459(4) 0.924(2) 0.636(3) 0.091(4) Uani d P 0.375(6) A 2
H H5' 0.5116 0.9619 0.6855 0.109 Uiso calc PR 0.375(6) A 2
C C6' 0.492(3) 0.8685(16) 0.598(2) 0.086(4) Uani d P 0.375(6) A 2
H H6' 0.5725 0.8445 0.6184 0.103 Uiso calc PR 0.375(6) A 2
C C7 0.1783(3) 0.6992(3) 0.3629(2) 0.0461(9) Uani d . 1 A .
C C8 0.1410(3) 0.7470(2) 0.4236(2) 0.0408(9) Uani d . 1 . .
C C9 0.0980(3) 0.6952(3) 0.4705(2) 0.0425(9) Uani d . 1 A .
C C10 0.0877(4) 0.5845(3) 0.4755(3) 0.0621(12) Uani d . 1 . .
H H10A 0.0024 0.5646 0.4395 0.093 Uiso calc R 1 A .
H H10B 0.1149 0.5652 0.5359 0.093 Uiso calc R 1 . .
H H10C 0.1390 0.5523 0.4542 0.093 Uiso calc R 1 . .
C C11 0.2614(4) 0.7310(3) 0.2650(3) 0.0666(12) Uani d . 1 . .
H H11A 0.1938 0.6969 0.2155 0.080 Uiso calc R 1 . .
H H11B 0.3299 0.6842 0.2946 0.080 Uiso calc R 1 . .
C C12 0.3030(4) 0.8203(4) 0.2328(3) 0.0828(15) Uani d . 1 . .
H H12A 0.2344 0.8660 0.2037 0.124 Uiso calc R 1 . .
H H12B 0.3312 0.7988 0.1918 0.124 Uiso calc R 1 . .
H H12C 0.3700 0.8533 0.2823 0.124 Uiso calc R 1 . .
C C13 0.9139(3) 0.6678(3) 0.6603(3) 0.0473(10) Uani d . 1 . .
C C14 0.7910(3) 0.6476(3) 0.7409(3) 0.0477(10) Uani d . 1 . .
H H14 0.8183 0.6161 0.7989 0.057 Uiso calc R 1 . .
C C15 0.6605(4) 0.6159(3) 0.6829(3) 0.0588(12) Uani d . 1 . .
C C16 0.5810(5) 0.5651(4) 0.7005(4) 0.0925(17) Uani d . 1 . .
H H16 0.5969 0.5387 0.7552 0.111 Uiso calc R 1 . .
C C17 0.4691(6) 0.5587(5) 0.6215(6) 0.113(2) Uani d . 1 . .
H H17 0.3961 0.5281 0.6141 0.136 Uiso calc R 1 . .
C C18 0.4851(6) 0.6031(6) 0.5604(6) 0.126(3) Uani d . 1 . .
H H18 0.4254 0.6087 0.5011 0.151 Uiso calc R 1 . .
C C19 0.7596(4) 0.8057(3) 0.8129(3) 0.0563(11) Uani d . 1 . .
C C20 0.8035(3) 0.7603(3) 0.7555(2) 0.0452(9) Uani d . 1 . .
C C21 0.8509(3) 0.8162(3) 0.7128(2) 0.0444(9) Uani d . 1 . .
C C22 0.8605(4) 0.9280(3) 0.7135(3) 0.0591(12) Uani d . 1 . .
H H22A 0.7799 0.9562 0.6756 0.089 Uiso calc R 1 . .
H H22B 0.9178 0.9474 0.6924 0.089 Uiso calc R 1 . .
H H22C 0.8901 0.9524 0.7729 0.089 Uiso calc R 1 . .
C C23 0.6852(5) 0.7708(4) 0.9158(3) 0.0831(15) Uani d . 1 . .
H H23A 0.6148 0.8154 0.8839 0.100 Uiso calc R 1 . .
H H23B 0.7496 0.8074 0.9654 0.100 Uiso calc R 1 . .
C C24 0.6464(5) 0.6833(5) 0.9477(4) 0.110(2) Uani d . 1 . .
H H24A 0.5780 0.6508 0.8987 0.165 Uiso calc R 1 . .
H H24B 0.6206 0.7041 0.9903 0.165 Uiso calc R 1 . .
H H24C 0.7150 0.6373 0.9753 0.165 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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 122.9(3) ?
C1 N1 H1 . . 118.6 ?
C2 N1 H1 . . 118.6 ?
C1 N2 C9 . . 123.9(3) ?
C1 N2 H2 . . 118.0 ?
C9 N2 H2 . . 118.0 ?
C13 N3 C14 . . 125.2(3) ?
C13 N3 H3 . . 117.4 ?
C14 N3 H3 . . 117.4 ?
C21 N4 C13 . . 125.1(3) ?
C21 N4 H4 . . 117.5 ?
C13 N4 H4 . . 117.5 ?
C3 O2 C6 . . 112.1(12) ?
C3 C4' C5' . . 101(2) ?
C3 C4' H4' . . 129.5 ?
C5' C4' H4' . . 129.5 ?
C7 O3 C11 . . 117.6(3) ?
C15 O6 C18 . . 106.5(5) ?
C19 O7 C23 . . 117.0(4) ?
O1 C1 N1 . . 123.9(4) ?
O1 C1 N2 . . 120.4(3) ?
N1 C1 N2 . . 115.6(3) ?
N1 C2 C3 . . 110.7(3) ?
N1 C2 C8 . . 109.4(3) ?
C3 C2 C8 . . 111.0(3) ?
N1 C2 H2A . . 108.5 ?
C3 C2 H2A . . 108.5 ?
C8 C2 H2A . . 108.5 ?
O2' C3 O2 . . 87.6(7) ?
O2' C3 C4 . . 44.8(5) ?
O2 C3 C4 . . 110.9(6) ?
O2' C3 C4' . . 104.6(10) ?
O2 C3 C4' . . 35.0(6) ?
C4 C3 C4' . . 101.9(9) ?
O2' C3 C2 . . 127.2(6) ?
O2 C3 C2 . . 120.8(5) ?
C4 C3 C2 . . 127.8(6) ?
C4' C3 C2 . . 124.4(9) ?
C3 C4 C5 . . 103.2(10) ?
C3 C4 H4A . . 128.4 ?
C5 C4 H4A . . 128.4 ?
C6 C5 C4 . . 109.5(15) ?
C6 C5 H5 . . 125.2 ?
C4 C5 H5 . . 125.2 ?
O2 C6 C5 . . 104.1(18) ?
O2 C6 H6 . . 127.9 ?
C5 C6 H6 . . 127.9 ?
C3 O2' C6' . . 113.1(15) ?
C6' C5' C4' . . 110(3) ?
C6' C5' H5' . . 125.2 ?
C4' C5' H5' . . 125.2 ?
C5' C6' O2' . . 108(3) ?
C5' C6' H6' . . 125.9 ?
O2' C6' H6' . . 125.9 ?
O4 C7 O3 . . 121.3(3) ?
O4 C7 C8 . . 127.4(3) ?
O3 C7 C8 . . 111.2(3) ?
C9 C8 C7 . . 122.9(3) ?
C9 C8 C2 . . 118.2(3) ?
C7 C8 C2 . . 118.9(3) ?
C8 C9 N2 . . 119.1(3) ?
C8 C9 C10 . . 127.9(3) ?
N2 C9 C10 . . 113.0(3) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O3 C11 C12 . . 107.3(4) ?
O3 C11 H11A . . 110.3 ?
C12 C11 H11A . . 110.3 ?
O3 C11 H11B . . 110.3 ?
C12 C11 H11B . . 110.3 ?
H11A C11 H11B . . 108.5 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O5 C13 N3 . . 124.2(4) ?
O5 C13 N4 . . 120.8(3) ?
N3 C13 N4 . . 115.0(4) ?
N3 C14 C15 . . 111.5(3) ?
N3 C14 C20 . . 110.5(3) ?
C15 C14 C20 . . 112.6(3) ?
N3 C14 H14 . . 107.3 ?
C15 C14 H14 . . 107.3 ?
C20 C14 H14 . . 107.3 ?
C16 C15 O6 . . 109.7(5) ?
C16 C15 C14 . . 131.2(5) ?
O6 C15 C14 . . 119.1(4) ?
C15 C16 C17 . . 107.0(6) ?
C15 C16 H16 . . 126.5 ?
C17 C16 H16 . . 126.5 ?
C18 C17 C16 . . 107.7(6) ?
C18 C17 H17 . . 126.2 ?
C16 C17 H17 . . 126.2 ?
C17 C18 O6 . . 109.1(7) ?
C17 C18 H18 . . 125.4 ?
O6 C18 H18 . . 125.4 ?
O8 C19 O7 . . 121.5(4) ?
O8 C19 C20 . . 127.3(4) ?
O7 C19 C20 . . 111.3(4) ?
C21 C20 C19 . . 121.7(4) ?
C21 C20 C14 . . 119.5(3) ?
C19 C20 C14 . . 118.8(3) ?
C20 C21 N4 . . 119.7(3) ?
C20 C21 C22 . . 126.7(3) ?
N4 C21 C22 . . 113.5(3) ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O7 C23 C24 . . 107.9(4) ?
O7 C23 H23A . . 110.1 ?
C24 C23 H23A . . 110.1 ?
O7 C23 H23B . . 110.1 ?
C24 C23 H23B . . 110.1 ?
H23A C23 H23B . . 108.4 ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
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
N1 C1 . 1.322(4) ?
N1 C2 . 1.454(4) ?
N1 H1 . 0.8600 ?
N2 C1 . 1.365(4) ?
N2 C9 . 1.379(4) ?
N2 H2 . 0.8600 ?
N3 C13 . 1.343(5) ?
N3 C14 . 1.454(4) ?
N3 H3 . 0.8600 ?
N4 C21 . 1.373(4) ?
N4 C13 . 1.377(4) ?
N4 H4 . 0.8600 ?
O1 C1 . 1.241(4) ?
O2 C3 . 1.263(8) ?
O2 C6 . 1.37(2) ?
C4' C3 . 1.44(2) ?
C4' C5' . 1.50(5) ?
C4' H4' . 0.9300 ?
O3 C7 . 1.338(4) ?
O3 C11 . 1.430(4) ?
O4 C7 . 1.211(4) ?
O5 C13 . 1.224(4) ?
O6 C15 . 1.330(6) ?
O6 C18 . 1.387(7) ?
O7 C19 . 1.337(5) ?
O7 C23 . 1.449(5) ?
O8 C19 . 1.201(4) ?
C2 C3 . 1.484(5) ?
C2 C8 . 1.509(5) ?
C2 H2A . 0.9800 ?
C3 O2' . 1.262(10) ?
C3 C4 . 1.387(10) ?
C4 C5 . 1.405(18) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.38(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
O2' C6' . 1.41(3) ?
C5' C6' . 1.17(6) ?
C5' H5' . 0.9300 ?
C6' H6' . 0.9300 ?
C7 C8 . 1.462(5) ?
C8 C9 . 1.339(5) ?
C9 C10 . 1.485(5) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.496(6) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C14 C15 . 1.480(5) ?
C14 C20 . 1.518(5) ?
C14 H14 . 0.9800 ?
C15 C16 . 1.327(6) ?
C16 C17 . 1.395(8) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.294(9) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 C20 . 1.455(5) ?
C20 C21 . 1.349(5) ?
C21 C22 . 1.494(5) ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C23 C24 . 1.458(7) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C24 H24C . 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 O1 3_576 0.86 2.12 2.924(4) 156.0
N2 H2 O5 1_455 0.86 2.02 2.851(4) 161.6
N3 H3 O4 3_666 0.86 2.38 3.077(4) 138.0
N4 H4 O1 1_655 0.86 2.10 2.952(4) 174.3
