#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/30/2213084.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_2213084
loop_
_publ_author_name
'B. K. Satis Kumar'
'D. Gayathri'
'D. Velmurugan'
'K. Ravikumar'
'E. Ramesh'
_publ_section_title
7-Allyl-1,3-dimethyl-2,4-dioxo-2,3,4,7-tetrahydro-1H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde
_journal_coeditor_code           AT2254
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2303
_journal_page_last               o2305
_journal_paper_doi               10.1107/S1600536807016170
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H13 N3 O3'
_chemical_formula_moiety         'C12 H13 N3 O3'
_chemical_formula_sum            'C12 H13 N3 O3'
_chemical_formula_weight         247.25
_chemical_name_systematic
;
7-Allyl-1,3-dimethyl-2,4-dioxo-2,3,4,7-tetrahydro-
1H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde
;
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.6130(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7065(4)
_cell_length_b                   13.1295(9)
_cell_length_c                   13.6977(9)
_cell_measurement_reflns_used    1396
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.16
_cell_volume                     1189.19(13)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_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 0.974
_diffrn_measurement_device       'Bruker SMART APEX'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       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  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13428
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0461
_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)+(0.0854P)²+0.1973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                2489
_reflns_number_total             2810
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2254.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2213084
_cod_database_fobs_code          2213084
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
C C1 0.02731(16) -0.07207(9) 0.62911(8) 0.0371(3) Uani d . 1
C C2 -0.0498(2) -0.24452(10) 0.58420(10) 0.0462(3) Uani d . 1
C C3 0.22504(19) -0.15765(9) 0.51776(9) 0.0429(3) Uani d . 1
C C4 0.18414(17) -0.07126(9) 0.57445(8) 0.0390(3) Uani d . 1
C C5 0.27974(19) 0.02346(9) 0.58915(9) 0.0444(3) Uani d . 1
H H5 0.3896 0.0455 0.5614 0.053 Uiso calc R 1
C C6 0.18148(19) 0.07780(9) 0.65212(9) 0.0432(3) Uani d . 1
C C7 0.2395(2) 0.17885(10) 0.68620(11) 0.0553(3) Uani d . 1
H H7 0.3502 0.2064 0.6627 0.066 Uiso calc R 1
C C8 -0.1007(2) 0.05064(10) 0.74942(10) 0.0488(3) Uani d . 1
H H8A -0.2413 0.0345 0.7250 0.059 Uiso calc R 1
H H8B -0.0902 0.1239 0.7577 0.059 Uiso calc R 1
C C9 -0.0388(3) 0.00112(11) 0.84735(10) 0.0570(4) Uani d . 1
H H9 -0.1149 0.0165 0.8963 0.068 Uiso calc R 1
C C10 0.1113(3) -0.06158(13) 0.87128(12) 0.0681(4) Uani d . 1
H H10A 0.1918 -0.0793 0.8249 0.082 Uiso calc R 1
H H10B 0.1382 -0.0887 0.9348 0.082 Uiso calc R 1
C C11 -0.2765(2) -0.15825(14) 0.67695(13) 0.0648(4) Uani d . 1
H H11A -0.2385 -0.1615 0.7476 0.097 Uiso calc R 1
H H11B -0.3556 -0.2171 0.6540 0.097 Uiso calc R 1
H H11C -0.3550 -0.0979 0.6593 0.097 Uiso calc R 1
C C12 0.1470(3) -0.33636(11) 0.47951(14) 0.0645(4) Uani d . 1
H H12A 0.0774 -0.3361 0.4123 0.097 Uiso calc R 1
H H12B 0.1018 -0.3932 0.5141 0.097 Uiso calc R 1
H H12C 0.2899 -0.3420 0.4801 0.097 Uiso calc R 1
N N1 -0.09448(15) -0.15558(8) 0.63114(8) 0.0422(3) Uani d . 1
N N2 0.10405(16) -0.24148(8) 0.52837(8) 0.0452(3) Uani d . 1
N N3 0.02182(15) 0.01889(8) 0.67575(7) 0.0402(3) Uani d . 1
O O1 -0.14554(19) -0.32202(8) 0.59072(9) 0.0697(3) Uani d . 1
O O2 0.35345(17) -0.16151(8) 0.46432(8) 0.0613(3) Uani d . 1
O O3 0.1630(2) 0.23281(9) 0.74150(10) 0.0750(4) 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 0.0033 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
_geom_angle_publ_flag
N3 C1 N1 129.14(10) ?
N3 C1 C4 109.22(10) ?
N1 C1 C4 121.64(10) ?
O1 C2 N2 121.14(12) ?
O1 C2 N1 120.84(13) ?
N2 C2 N1 118.02(10) ?
O2 C3 N2 120.83(12) ?
O2 C3 C4 125.33(12) ?
N2 C3 C4 113.84(10) ?
C1 C4 C5 107.43(10) ?
C1 C4 C3 121.25(10) ?
C5 C4 C3 131.31(11) ?
C6 C5 C4 107.25(11) ?
C6 C5 H5 126.4 ?
C4 C5 H5 126.4 ?
C5 C6 N3 108.92(11) ?
C5 C6 C7 123.52(12) ?
N3 C6 C7 127.55(12) ?
O3 C7 C6 128.50(14) ?
O3 C7 H7 115.7 ?
C6 C7 H7 115.7 ?
N3 C8 C9 113.16(11) ?
N3 C8 H8A 108.9 ?
C9 C8 H8A 108.9 ?
N3 C8 H8B 108.9 ?
C9 C8 H8B 108.9 ?
H8A C8 H8B 107.8 ?
C10 C9 C8 126.35(13) ?
C10 C9 H9 116.8 ?
C8 C9 H9 116.8 ?
C9 C10 H10A 120.0 ?
C9 C10 H10B 120.0 ?
H10A C10 H10B 120.0 ?
N1 C11 H11A 109.5 ?
N1 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
N1 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
N2 C12 H12A 109.5 ?
N2 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
N2 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C1 N1 C2 119.20(10) y
C1 N1 C11 124.80(10) y
C2 N1 C11 116.00(10) y
C2 N2 C3 125.70(10) y
C2 N2 C12 116.70(10) y
C3 N2 C12 117.60(10) y
C1 N3 C6 107.20(10) y
C1 N3 C8 129.60(10) y
C6 N3 C8 122.70(10) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N3 1.358(2) y
C1 N1 1.370(2) y
C1 C4 1.389(2) ?
C2 O1 1.214(2) y
C2 N2 1.384(2) y
C2 N1 1.390(2) y
C3 O2 1.221(2) y
C3 N2 1.389(2) y
C3 C4 1.4269(17) ?
C4 C5 1.3983(17) ?
C5 C6 1.3700(18) ?
C5 H5 0.9300 ?
C6 N3 1.402(2) y
C6 C7 1.438(2) ?
C7 O3 1.212(2) y
C7 H7 0.9300 ?
C8 N3 1.464(2) y
C8 C9 1.486(2) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 C10 1.299(2) ?
C9 H9 0.9300 ?
C10 H10A 0.9300 ?
C10 H10B 0.9300 ?
C11 N1 1.464(2) y
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C12 N2 1.465(2) y
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 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
C5 H5 O2 3_656 0.93 2.37 3.237(2) 155.0
C8 H8B O3 . 0.97 2.26 2.987(2) 131.1
C10 H10A N3 . 0.93 2.52 2.848(2) 101.0
C11 H11B O1 . 0.96 2.25 2.671(2) 105.8
C12 H12B O1 . 0.96 2.30 2.684(2) 102.7
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
N3 C1 C4 C5 0.70(13)
N1 C1 C4 C5 -179.15(11)
N3 C1 C4 C3 179.94(10)
N1 C1 C4 C3 0.09(17)
O2 C3 C4 C1 176.45(13)
N2 C3 C4 C1 -3.96(17)
O2 C3 C4 C5 -4.5(2)
N2 C3 C4 C5 175.08(12)
C1 C4 C5 C6 0.32(14)
C3 C4 C5 C6 -178.82(12)
C4 C5 C6 N3 -1.18(14)
C4 C5 C6 C7 178.77(12)
C5 C6 C7 O3 -179.96(16)
N3 C6 C7 O3 0.0(3)
N3 C8 C9 C10 2.4(2)
N3 C1 N1 C2 -174.35(11)
C4 C1 N1 C2 5.46(17)
N3 C1 N1 C11 7.8(2)
C4 C1 N1 C11 -172.34(13)
O1 C2 N1 C1 174.55(13)
N2 C2 N1 C1 -6.70(17)
O1 C2 N1 C11 -7.5(2)
N2 C2 N1 C11 171.29(12)
O1 C2 N2 C3 -178.58(13)
N1 C2 N2 C3 2.67(19)
O1 C2 N2 C12 -1.0(2)
N1 C2 N2 C12 -179.78(12)
O2 C3 N2 C2 -177.79(13)
C4 C3 N2 C2 2.60(18)
O2 C3 N2 C12 4.67(19)
C4 C3 N2 C12 -174.93(12)
N1 C1 N3 C6 178.43(11)
C4 C1 N3 C6 -1.41(13)
N1 C1 N3 C8 7.1(2)
C4 C1 N3 C8 -172.70(11)
C5 C6 N3 C1 1.62(14)
C7 C6 N3 C1 -178.33(13)
C5 C6 N3 C8 173.65(11)
C7 C6 N3 C8 -6.3(2)
C9 C8 N3 C1 70.55(17)
C9 C8 N3 C6 -99.56(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124880
