#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/68/2226849.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_2226849
loop_
_publ_author_name
'Sachdeva, Nikhil'
'Dolzhenko, Anton V.'
'Tan, Geok Kheng'
'Koh, Lip Lin'
'Chui, Wai Keung'
_publ_section_title
;
 4-Amino-2,8-dimethyl-6H-pyrimido[1,2-a][1,3,5]triazin-6-one
;
_journal_coeditor_code           EZ2220
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2050
_journal_paper_doi               10.1107/S1600536810027522
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H9 N5 O'
_chemical_formula_moiety         'C8 H9 N5 O'
_chemical_formula_sum            'C8 H9 N5 O'
_chemical_formula_weight         191.20
_chemical_melting_point          545
_chemical_name_systematic
;
4-Amino-2,8-dimethyl-6H-pyrimido[1,2-a][1,3,5]triazin-6-one
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1369(19)
_cell_length_b                   18.913(3)
_cell_length_c                   4.0311(7)
_cell_measurement_reflns_used    614
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.80
_cell_measurement_theta_min      2.83
_cell_volume                     849.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5774
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1119
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0527
_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)+(0.0530P)²+0.4545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                1019
_reflns_number_total             1119
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2220.cif
_cod_data_source_block           I
_cod_original_cell_volume        849.1(3)
_cod_database_code               2226849
_cod_database_fobs_code          2226849
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.61240(19) 0.88225(11) -0.2411(7) 0.0229(6) Uani d . 1 . .
N N1 0.3706(2) 0.71578(13) 0.3214(8) 0.0145(6) Uani d . 1 . .
N N2 0.5341(2) 0.67258(13) -0.0011(7) 0.0137(6) Uani d . 1 . .
N N3 0.4963(2) 0.79702(13) 0.0265(7) 0.0119(5) Uani d . 1 . .
N N4 0.3255(2) 0.83294(13) 0.3415(7) 0.0138(6) Uani d . 1 . .
N N5 0.6531(2) 0.74865(15) -0.2904(7) 0.0154(6) Uani d . 1 . .
H H51 0.673(3) 0.793(2) -0.326(11) 0.018(9) Uiso d . 1 . .
H H52 0.689(3) 0.7098(19) -0.349(11) 0.019(9) Uiso d . 1 . .
C C1 0.4393(3) 0.66472(15) 0.2008(8) 0.0134(6) Uani d . 1 . .
C C2 0.5625(2) 0.73778(15) -0.0888(8) 0.0128(6) Uani d . 1 . .
C C3 0.3965(2) 0.78262(15) 0.2314(8) 0.0121(6) Uani d . 1 . .
C C4 0.3465(2) 0.90073(15) 0.2475(9) 0.0139(6) Uani d . 1 . .
C C5 0.4418(3) 0.91978(16) 0.0552(8) 0.0147(6) Uani d . 1 . .
H H5 0.4531 0.9683 0.0019 0.018 Uiso calc R 1 . .
C C6 0.5246(3) 0.86906(15) -0.0674(8) 0.0155(7) Uani d . 1 . .
C C7 0.4091(3) 0.59100(15) 0.3046(10) 0.0191(7) Uani d . 1 . .
H H7A 0.4559 0.5784 0.5017 0.029 Uiso calc R 1 . .
H H7B 0.4282 0.5582 0.1239 0.029 Uiso calc R 1 . .
H H7C 0.3232 0.5880 0.3562 0.029 Uiso calc R 1 . .
C C8 0.2543(3) 0.95324(15) 0.3617(9) 0.0182(7) Uani d . 1 . .
H H8A 0.1796 0.9460 0.2381 0.027 Uiso calc R 1 . .
H H8B 0.2840 1.0013 0.3224 0.027 Uiso calc R 1 . .
H H8C 0.2392 0.9467 0.5992 0.027 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 C3 . . 117.5(3) ?
C2 N2 C1 . . 117.0(2) ?
C3 N3 C2 . . 116.6(2) ?
C3 N3 C6 . . 120.4(2) ?
C2 N3 C6 . . 122.9(2) ?
C3 N4 C4 . . 119.1(3) ?
C2 N5 H51 . . 116(2) ?
C2 N5 H52 . . 113(2) ?
H51 N5 H52 . . 130(3) ?
N1 C1 N2 . . 126.6(3) ?
N1 C1 C7 . . 116.6(3) ?
N2 C1 C7 . . 116.8(3) ?
N5 C2 N2 . . 119.7(3) ?
N5 C2 N3 . . 118.6(3) ?
N2 C2 N3 . . 121.6(3) ?
N4 C3 N1 . . 117.4(3) ?
N4 C3 N3 . . 122.1(3) ?
N1 C3 N3 . . 120.5(3) ?
N4 C4 C5 . . 122.9(3) ?
N4 C4 C8 . . 114.9(3) ?
C5 C4 C8 . . 122.2(3) ?
C4 C5 C6 . . 121.7(3) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
O1 C6 C5 . . 125.3(3) ?
O1 C6 N3 . . 120.9(3) ?
C5 C6 N3 . . 113.8(3) ?
C1 C7 H7A . . 109.5 ?
C1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C4 C8 H8A . . 109.5 ?
C4 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C4 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 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 C6 . 1.228(4) ?
N1 C1 . 1.324(4) ?
N1 C3 . 1.346(4) ?
N2 C2 . 1.321(4) ?
N2 C1 . 1.342(4) ?
N3 C3 . 1.411(4) ?
N3 C2 . 1.420(4) ?
N3 C6 . 1.449(4) ?
N4 C3 . 1.314(4) ?
N4 C4 . 1.357(4) ?
N5 C2 . 1.311(4) ?
N5 H51 . 0.89(4) ?
N5 H52 . 0.87(4) ?
C1 C7 . 1.494(4) ?
C4 C5 . 1.363(4) ?
C4 C8 . 1.501(4) ?
C5 C6 . 1.420(4) ?
C5 H5 . 0.9500 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
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
N5 H51 O1 . 0.89(4) 1.84(4) 2.575(3) 139(3)
N5 H51 N1 3_564 0.89(4) 2.63(4) 2.961(4) 103(3)
N5 H52 N4 3_564 0.87(4) 2.12(4) 2.876(4) 144(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
C3 N1 C1 N2 . . . . 0.9(5) ?
C3 N1 C1 C7 . . . . 179.8(3) ?
C2 N2 C1 N1 . . . . 0.2(5) ?
C2 N2 C1 C7 . . . . -178.8(3) ?
C1 N2 C2 N5 . . . . -178.8(3) ?
C1 N2 C2 N3 . . . . 0.4(4) ?
C3 N3 C2 N5 . . . . 177.4(3) ?
C6 N3 C2 N5 . . . . -0.3(4) ?
C3 N3 C2 N2 . . . . -1.8(4) ?
C6 N3 C2 N2 . . . . -179.5(3) ?
C4 N4 C3 N1 . . . . -177.9(3) ?
C4 N4 C3 N3 . . . . 2.0(4) ?
C1 N1 C3 N4 . . . . 177.5(3) ?
C1 N1 C3 N3 . . . . -2.4(4) ?
C2 N3 C3 N4 . . . . -177.1(3) ?
C6 N3 C3 N4 . . . . 0.7(4) ?
C2 N3 C3 N1 . . . . 2.8(4) ?
C6 N3 C3 N1 . . . . -179.4(3) ?
C3 N4 C4 C5 . . . . -3.2(5) ?
C3 N4 C4 C8 . . . . 174.9(3) ?
N4 C4 C5 C6 . . . . 1.6(5) ?
C8 C4 C5 C6 . . . . -176.3(3) ?
C4 C5 C6 O1 . . . . -179.9(3) ?
C4 C5 C6 N3 . . . . 1.0(4) ?
C3 N3 C6 O1 . . . . 178.8(3) ?
C2 N3 C6 O1 . . . . -3.6(4) ?
C3 N3 C6 C5 . . . . -2.1(4) ?
C2 N3 C6 C5 . . . . 175.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26000886
