#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/65/2226595.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_2226595
loop_
_publ_author_name
'Zubatyuk, Roman I.'
'Shishkin, Oleg V.'
'Ihmels, Heiko'
'Lebedyeva, Iryna A.'
'Povstyanoy, Mykhaylo V.'
_publ_section_title
;
 Ethyl
 1,6-dimethyl-2-oxo-4-(quinolin-4-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
;
_journal_coeditor_code           LX2153
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1762
_journal_page_last               o1763
_journal_paper_doi               10.1107/S1600536810023482
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H19 N3 O3'
_chemical_formula_moiety         'C18 H19 N3 O3'
_chemical_formula_sum            'C18 H19 N3 O3'
_chemical_formula_weight         325.36
_chemical_name_systematic
;
Ethyl
1,6-dimethyl-2-oxo-4-(quinolin-4-yl)-1,2,3,4-tetrahydropyrimidine-5-
carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                110.799(10)
_cell_angle_beta                 95.807(9)
_cell_angle_gamma                97.339(9)
_cell_formula_units_Z            2
_cell_length_a                   8.5039(10)
_cell_length_b                   9.4637(11)
_cell_length_c                   10.7503(11)
_cell_measurement_reflns_used    3300
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.4311
_cell_measurement_theta_min      3.0639
_cell_volume                     792.08(17)
_computing_cell_refinement
;
CrysAlisPro (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlisPro (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlisPro (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'Platon (Spek, 2009)'
_computing_publication_material  'publcif (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur diffractometer with Sapphire3 detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8517
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         3.0639
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.97447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                2810
_reflns_number_total             4607
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lx2153.cif
_cod_data_source_block           I
_cod_original_cell_volume        792.07(17)
_cod_database_code               2226595
_cod_database_fobs_code          2226595
loop_
_space_group_symop_operation_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.27163(12) 0.04049(12) 0.18120(11) 0.0531(3) Uani d . 1 . .
O O2 0.06327(12) -0.03288(11) 0.26749(11) 0.0499(3) Uani d . 1 . .
O O3 -0.17806(12) 0.43713(11) 0.03648(11) 0.0505(3) Uani d . 1 . .
N N1 -0.19236(12) 0.24916(11) 0.12189(11) 0.0342(2) Uani d . 1 . .
N N2 0.05174(13) 0.36177(12) 0.09001(11) 0.0392(3) Uani d . 1 . .
H H2 0.1019 0.4088 0.0464 0.047 Uiso calc R 1 . .
N N3 0.34211(15) 0.63743(12) 0.56698(12) 0.0471(3) Uani d . 1 . .
C C1 0.14609(14) 0.29466(13) 0.16757(12) 0.0315(3) Uani d . 1 . .
H H1 0.2345 0.2599 0.1197 0.038 Uiso calc R 1 . .
C C2 0.04233(15) 0.15552(12) 0.17321(12) 0.0317(3) Uani d . 1 . .
C C3 -0.11880(15) 0.13846(13) 0.15232(12) 0.0324(3) Uani d . 1 . .
C C4 -0.10723(16) 0.35587(13) 0.08131(13) 0.0355(3) Uani d . 1 . .
C C5 0.21887(13) 0.41308(12) 0.30752(12) 0.0297(3) Uani d . 1 . .
C C6 0.16516(16) 0.40622(14) 0.42047(13) 0.0377(3) Uani d . 1 . .
H H6 0.0850 0.3261 0.4139 0.045 Uiso calc R 1 . .
C C7 0.23041(18) 0.51977(16) 0.54688(15) 0.0467(3) Uani d . 1 . .
H H7 0.1913 0.5106 0.6219 0.056 Uiso calc R 1 . .
C C8 0.40063(15) 0.64740(14) 0.45630(14) 0.0385(3) Uani d . 1 . .
C C9 0.52172(17) 0.77391(15) 0.47649(16) 0.0497(4) Uani d . 1 . .
H H9 0.5580 0.8462 0.5631 0.060 Uiso calc R 1 . .
C C10 0.58558(18) 0.79118(17) 0.37115(18) 0.0562(4) Uani d . 1 . .
H H10 0.6645 0.8754 0.3856 0.067 Uiso calc R 1 . .
C C11 0.53288(17) 0.68249(17) 0.24086(17) 0.0519(4) Uani d . 1 . .
H H11 0.5785 0.6942 0.1693 0.062 Uiso calc R 1 . .
C C12 0.41510(15) 0.55914(15) 0.21731(15) 0.0390(3) Uani d . 1 . .
H H12 0.3810 0.4886 0.1298 0.047 Uiso calc R 1 . .
C C13 0.34461(13) 0.53745(13) 0.32394(13) 0.0315(3) Uani d . 1 . .
C C14 0.13704(16) 0.04890(13) 0.20431(13) 0.0356(3) Uani d . 1 . .
C C15 0.14436(18) -0.14639(16) 0.29605(17) 0.0488(4) Uani d . 1 . .
H H15B 0.2456 -0.0972 0.3555 0.059 Uiso calc R 1 . .
H H15A 0.1659 -0.2207 0.2133 0.059 Uiso calc R 1 . .
C C16 0.0369(2) -0.2227(2) 0.3611(2) 0.0799(7) Uani d . 1 . .
H H16B 0.0163 -0.1479 0.4426 0.120 Uiso calc R 1 . .
H H16C 0.0869 -0.2987 0.3820 0.120 Uiso calc R 1 . .
H H16A -0.0625 -0.2712 0.3011 0.120 Uiso calc R 1 . .
C C17 -0.23434(17) 0.00572(15) 0.15444(17) 0.0485(4) Uani d . 1 . .
H H17C -0.2872 0.0395 0.2319 0.073 Uiso calc R 1 . .
H H17A -0.1769 -0.0738 0.1587 0.073 Uiso calc R 1 . .
H H17B -0.3128 -0.0334 0.0741 0.073 Uiso calc R 1 . .
C C18 -0.36752(16) 0.23559(17) 0.09982(16) 0.0475(4) Uani d . 1 . .
H H18B -0.4112 0.2070 0.1682 0.071 Uiso calc R 1 . .
H H18A -0.4111 0.1585 0.0127 0.071 Uiso calc R 1 . .
H H18C -0.3949 0.3324 0.1041 0.071 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 0 '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 0.006 '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
C14 O2 C15 . . 117.81(10) ?
C4 N1 C3 . . 121.22(10) ?
C4 N1 C18 . . 115.73(10) ?
C3 N1 C18 . . 121.48(10) ?
C4 N2 C1 . . 124.96(10) ?
C4 N2 H2 . . 117.5 ?
C1 N2 H2 . . 117.5 ?
C7 N3 C8 . . 116.88(12) ?
N2 C1 C2 . . 108.97(10) ?
N2 C1 C5 . . 111.30(9) ?
C2 C1 C5 . . 112.65(10) ?
N2 C1 H1 . . 107.9 ?
C2 C1 H1 . . 107.9 ?
C5 C1 H1 . . 107.9 ?
C3 C2 C14 . . 126.27(11) ?
C3 C2 C1 . . 120.96(10) ?
C14 C2 C1 . . 112.77(10) ?
C2 C3 N1 . . 119.79(10) ?
C2 C3 C17 . . 125.97(11) ?
N1 C3 C17 . . 114.21(11) ?
O3 C4 N2 . . 122.75(11) ?
O3 C4 N1 . . 120.25(12) ?
N2 C4 N1 . . 116.98(10) ?
C6 C5 C13 . . 117.48(11) ?
C6 C5 C1 . . 121.55(10) ?
C13 C5 C1 . . 120.96(10) ?
C5 C6 C7 . . 120.17(12) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
N3 C7 C6 . . 124.77(13) ?
N3 C7 H7 . . 117.6 ?
C6 C7 H7 . . 117.6 ?
N3 C8 C9 . . 117.53(13) ?
N3 C8 C13 . . 122.88(11) ?
C9 C8 C13 . . 119.59(13) ?
C10 C9 C8 . . 120.78(14) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C9 C10 C11 . . 120.05(13) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C12 C11 C10 . . 120.81(14) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C11 C12 C13 . . 120.95(13) ?
C11 C12 H12 . . 119.5 ?
C13 C12 H12 . . 119.5 ?
C12 C13 C8 . . 117.82(11) ?
C12 C13 C5 . . 124.39(12) ?
C8 C13 C5 . . 117.79(11) ?
O1 C14 O2 . . 122.41(11) ?
O1 C14 C2 . . 123.48(11) ?
O2 C14 C2 . . 114.03(11) ?
O2 C15 C16 . . 106.99(11) ?
O2 C15 H15B . . 110.3 ?
C16 C15 H15B . . 110.3 ?
O2 C15 H15A . . 110.3 ?
C16 C15 H15A . . 110.3 ?
H15B C15 H15A . . 108.6 ?
C15 C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C15 C16 H16A . . 109.5 ?
H16B C16 H16A . . 109.5 ?
H16C C16 H16A . . 109.5 ?
C3 C17 H17C . . 109.5 ?
C3 C17 H17A . . 109.5 ?
H17C C17 H17A . . 109.5 ?
C3 C17 H17B . . 109.5 ?
H17C C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N1 C18 H18B . . 109.5 ?
N1 C18 H18A . . 109.5 ?
H18B C18 H18A . . 109.5 ?
N1 C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
H18A C18 H18C . . 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
O1 C14 . 1.2018(15) ?
O2 C14 . 1.3377(15) ?
O2 C15 . 1.4504(14) ?
O3 C4 . 1.2283(14) ?
N1 C4 . 1.3871(15) ?
N1 C3 . 1.4019(14) ?
N1 C18 . 1.4662(16) ?
N2 C4 . 1.3380(16) ?
N2 C1 . 1.4538(14) ?
N2 H2 . 0.8600 ?
N3 C7 . 1.3061(17) ?
N3 C8 . 1.3637(18) ?
C1 C2 . 1.5122(15) ?
C1 C5 . 1.5293(17) ?
C1 H1 . 0.9800 ?
C2 C3 . 1.3451(17) ?
C2 C14 . 1.4735(16) ?
C3 C17 . 1.5012(16) ?
C5 C6 . 1.3591(17) ?
C5 C13 . 1.4330(15) ?
C6 C7 . 1.4022(19) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.4125(18) ?
C8 C13 . 1.4207(18) ?
C9 C10 . 1.356(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.397(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.3676(18) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.4103(18) ?
C12 H12 . 0.9300 ?
C15 C16 . 1.471(2) ?
C15 H15B . 0.9700 ?
C15 H15A . 0.9700 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C16 H16A . 0.9600 ?
C17 H17C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18C . 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
_geom_hbond_publ_flag
N2 H2 O3 2_565 0.86 2.03 2.8701(16) 164 yes
C17 H17A O2 . 0.96 2.16 2.8187(19) 124 yes
C16 H16C Cg1 1_545 0.96 2.66 3.603(2) 168 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
C4 N2 C1 C2 . . . . 29.78(16) ?
C4 N2 C1 C5 . . . . -95.05(13) ?
N2 C1 C2 C3 . . . . -21.57(16) ?
C5 C1 C2 C3 . . . . 102.47(13) ?
N2 C1 C2 C14 . . . . 159.04(10) ?
C5 C1 C2 C14 . . . . -76.92(13) ?
C14 C2 C3 N1 . . . . -179.22(11) ?
C1 C2 C3 N1 . . . . 1.47(18) ?
C14 C2 C3 C17 . . . . -1.0(2) ?
C1 C2 C3 C17 . . . . 179.65(12) ?
C4 N1 C3 C2 . . . . 15.51(18) ?
C18 N1 C3 C2 . . . . -179.37(12) ?
C4 N1 C3 C17 . . . . -162.87(11) ?
C18 N1 C3 C17 . . . . 2.25(17) ?
C1 N2 C4 O3 . . . . 165.93(12) ?
C1 N2 C4 N1 . . . . -15.95(18) ?
C3 N1 C4 O3 . . . . 169.42(12) ?
C18 N1 C4 O3 . . . . 3.50(18) ?
C3 N1 C4 N2 . . . . -8.75(18) ?
C18 N1 C4 N2 . . . . -174.68(12) ?
N2 C1 C5 C6 . . . . 109.13(12) ?
C2 C1 C5 C6 . . . . -13.61(15) ?
N2 C1 C5 C13 . . . . -69.65(13) ?
C2 C1 C5 C13 . . . . 167.60(10) ?
C13 C5 C6 C7 . . . . 1.16(17) ?
C1 C5 C6 C7 . . . . -177.67(11) ?
C8 N3 C7 C6 . . . . -1.4(2) ?
C5 C6 C7 N3 . . . . 0.6(2) ?
C7 N3 C8 C9 . . . . -179.87(13) ?
C7 N3 C8 C13 . . . . 0.41(19) ?
N3 C8 C9 C10 . . . . 179.93(13) ?
C13 C8 C9 C10 . . . . -0.3(2) ?
C8 C9 C10 C11 . . . . -0.6(2) ?
C9 C10 C11 C12 . . . . 1.0(2) ?
C10 C11 C12 C13 . . . . -0.6(2) ?
C11 C12 C13 C8 . . . . -0.31(18) ?
C11 C12 C13 C5 . . . . 178.85(12) ?
N3 C8 C13 C12 . . . . -179.52(11) ?
C9 C8 C13 C12 . . . . 0.77(17) ?
N3 C8 C13 C5 . . . . 1.27(17) ?
C9 C8 C13 C5 . . . . -178.45(11) ?
C6 C5 C13 C12 . . . . 178.85(11) ?
C1 C5 C13 C12 . . . . -2.32(17) ?
C6 C5 C13 C8 . . . . -1.99(15) ?
C1 C5 C13 C8 . . . . 176.84(10) ?
C15 O2 C14 O1 . . . . -6.3(2) ?
C15 O2 C14 C2 . . . . 176.97(11) ?
C3 C2 C14 O1 . . . . 155.76(13) ?
C1 C2 C14 O1 . . . . -24.89(18) ?
C3 C2 C14 O2 . . . . -27.58(19) ?
C1 C2 C14 O2 . . . . 151.78(11) ?
C14 O2 C15 C16 . . . . -178.22(14) ?
