#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/80/2018083.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_2018083
loop_
_publ_author_name
'Gerhardt, Valeska'
'Tutughamiarso, Maya'
'Bolte, Michael'
_publ_section_title
;
 Pseudopolymorphs of 2,6-diaminopyrimidin-4-one and
 2-amino-6-methylpyrimidin-4-one: one or two tautomers present in the
 same crystal
;
_journal_coeditor_code           SK3407
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o179
_journal_page_last               o187
_journal_paper_doi               10.1107/S0108270111013072
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C5 H7 N3 O , C5 H7 N3 O , C4 H9 N O'
_chemical_formula_moiety         '2(C5 H7 N3 O), C4 H9 N O'
_chemical_formula_sum            'C14 H23 N7 O3'
_chemical_formula_weight         337.39
_chemical_name_systematic
;
2-amino-6-methylpyrimidin-4(3H)-one--2-amino-6-methylpyrimidin-\
4(1H)-one--dimethylacetamide (1/1/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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           SHELXL97
_cell_angle_alpha                108.780(13)
_cell_angle_beta                 95.194(13)
_cell_angle_gamma                99.959(13)
_cell_formula_units_Z            2
_cell_length_a                   7.8763(13)
_cell_length_b                   9.6078(17)
_cell_length_c                   12.3115(19)
_cell_measurement_reflns_used    2325
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.91
_cell_measurement_theta_min      3.4
_cell_volume                     858.0(3)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics
;
Mercury (Version 2.2; Macrae et al., 2008) and XP (Sheldrick,
2008)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_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  0.1314
_diffrn_reflns_av_sigmaI/netI    0.1558
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7199
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_min         3.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.466
_refine_ls_extinction_coef       0.018(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.819
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0678
_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)+(0.1094P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1797
_refine_ls_wR_factor_ref         0.2043
_reflns_number_gt                1427
_reflns_number_total             3208
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3407.cif
_cod_data_source_block           IIa
_cod_original_cell_volume        858.0(2)
_cod_database_code               2018083
_cod_database_fobs_code          2018083
loop_
_symmetry_equiv_pos_as_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
N N1A 0.1822(4) 0.6323(4) 0.4673(3) 0.0313(8) Uani d . 1 . .
H H1A 0.1566 0.6699 0.5375 0.038 Uiso calc R 1 . .
C C2A 0.2487(5) 0.5060(4) 0.4397(3) 0.0297(9) Uani d . 1 . .
N N21A 0.2741(4) 0.4471(4) 0.5222(3) 0.0398(9) Uani d . 1 . .
H H21A 0.3160 0.3649 0.5073 0.048 Uiso calc R 1 . .
H H21B 0.2491 0.4903 0.5918 0.048 Uiso calc R 1 . .
N N3A 0.2863(4) 0.4411(4) 0.3346(3) 0.0295(8) Uani d . 1 . .
C C4A 0.2594(5) 0.5053(4) 0.2508(3) 0.0264(8) Uani d . 1 . .
O O41A 0.2933(4) 0.4439(3) 0.1509(2) 0.0359(7) Uani d . 1 . .
C C5A 0.1922(5) 0.6414(5) 0.2810(3) 0.0350(10) Uani d . 1 . .
H H5A 0.1748 0.6880 0.2248 0.042 Uiso calc R 1 . .
C C6A 0.1541(5) 0.7026(4) 0.3887(3) 0.0317(9) Uani d . 1 . .
C C61A 0.0839(6) 0.8407(5) 0.4293(4) 0.0438(11) Uani d . 1 . .
H H61A 0.1733 0.9216 0.4860 0.066 Uiso calc R 1 . .
H H61B -0.0189 0.8208 0.4658 0.066 Uiso calc R 1 . .
H H61C 0.0507 0.8710 0.3630 0.066 Uiso calc R 1 . .
N N1B 0.5073(4) -0.0211(3) 0.1427(2) 0.0274(7) Uani d . 1 . .
C C2B 0.4440(4) 0.1017(4) 0.1717(3) 0.0241(8) Uani d . 1 . .
N N21B 0.4036(4) 0.1620(4) 0.0915(2) 0.0308(8) Uani d . 1 . .
H H21C 0.4194 0.1196 0.0194 0.037 Uiso calc R 1 . .
H H21D 0.3613 0.2441 0.1108 0.037 Uiso calc R 1 . .
N N3B 0.4118(4) 0.1701(4) 0.2808(2) 0.0254(7) Uani d . 1 . .
H H3B 0.3701 0.2524 0.2947 0.030 Uiso calc R 1 . .
C C4B 0.4413(5) 0.1168(5) 0.3705(3) 0.0306(9) Uani d . 1 . .
O O41B 0.4064(4) 0.1843(3) 0.4680(2) 0.0408(8) Uani d . 1 . .
C C5B 0.5096(5) -0.0174(4) 0.3406(3) 0.0303(9) Uani d . 1 . .
H H5B 0.5334 -0.0625 0.3970 0.036 Uiso calc R 1 . .
C C6B 0.5399(5) -0.0791(4) 0.2293(3) 0.0282(9) Uani d . 1 . .
C C61B 0.6104(6) -0.2198(5) 0.1948(3) 0.0381(10) Uani d . 1 . .
H H61D 0.5181 -0.3044 0.1449 0.057 Uiso calc R 1 . .
H H61E 0.6512 -0.2403 0.2646 0.057 Uiso calc R 1 . .
H H61F 0.7079 -0.2065 0.1524 0.057 Uiso calc R 1 . .
C C1X 0.0469(6) 0.8732(5) 0.8135(4) 0.0471(12) Uani d . 1 . .
H H1X1 0.0320 0.8923 0.7401 0.071 Uiso calc R 1 . .
H H1X2 0.1235 0.9611 0.8731 0.071 Uiso calc R 1 . .
H H1X3 -0.0672 0.8541 0.8382 0.071 Uiso calc R 1 . .
C C2X 0.1269(5) 0.7381(5) 0.7971(3) 0.0367(10) Uani d . 1 . .
O O2X 0.1735(4) 0.6728(4) 0.7028(2) 0.0436(8) Uani d . 1 . .
N N3X 0.1524(5) 0.6883(4) 0.8854(3) 0.0418(9) Uani d . 1 . .
C C4X 0.2320(7) 0.5590(6) 0.8719(5) 0.0606(15) Uani d . 1 . .
H H4X1 0.1507 0.4677 0.8198 0.091 Uiso calc R 1 . .
H H4X2 0.2593 0.5489 0.9479 0.091 Uiso calc R 1 . .
H H4X3 0.3397 0.5734 0.8389 0.091 Uiso calc R 1 . .
C C5X 0.0938(7) 0.7573(7) 0.9971(4) 0.0661(17) Uani d . 1 . .
H H5X1 0.0295 0.8337 0.9909 0.099 Uiso calc R 1 . .
H H5X2 0.1956 0.8045 1.0583 0.099 Uiso calc R 1 . .
H H5X3 0.0176 0.6795 1.0164 0.099 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
C2A N1A C6A . . 121.7(3) ?
C2A N1A H1A . . 119.1 ?
C6A N1A H1A . . 119.1 ?
N3A C2A N21A . . 120.2(4) ?
N3A C2A N1A . . 122.4(4) ?
N21A C2A N1A . . 117.4(3) ?
C2A N21A H21A . . 120.0 ?
C2A N21A H21B . . 120.0 ?
H21A N21A H21B . . 120.0 ?
C2A N3A C4A . . 118.9(3) ?
O41A C4A N3A . . 119.3(3) ?
O41A C4A C5A . . 122.1(4) ?
N3A C4A C5A . . 118.7(3) ?
C6A C5A C4A . . 120.4(4) ?
C6A C5A H5A . . 119.8 ?
C4A C5A H5A . . 119.8 ?
C5A C6A N1A . . 117.9(4) ?
C5A C6A C61A . . 125.2(4) ?
N1A C6A C61A . . 116.9(3) ?
C6A C61A H61A . . 109.5 ?
C6A C61A H61B . . 109.5 ?
H61A C61A H61B . . 109.5 ?
C6A C61A H61C . . 109.5 ?
H61A C61A H61C . . 109.5 ?
H61B C61A H61C . . 109.5 ?
C2B N1B C6B . . 116.4(3) ?
N1B C2B N21B . . 119.9(3) ?
N1B C2B N3B . . 122.9(3) ?
N21B C2B N3B . . 117.1(3) ?
C2B N21B H21C . . 120.0 ?
C2B N21B H21D . . 120.0 ?
H21C N21B H21D . . 120.0 ?
C2B N3B C4B . . 123.1(3) ?
C2B N3B H3B . . 118.4 ?
C4B N3B H3B . . 118.4 ?
O41B C4B N3B . . 119.6(4) ?
O41B C4B C5B . . 125.5(4) ?
N3B C4B C5B . . 114.9(3) ?
C6B C5B C4B . . 118.6(4) ?
C6B C5B H5B . . 120.7 ?
C4B C5B H5B . . 120.7 ?
N1B C6B C5B . . 124.1(4) ?
N1B C6B C61B . . 115.8(3) ?
C5B C6B C61B . . 120.1(4) ?
C6B C61B H61D . . 109.5 ?
C6B C61B H61E . . 109.5 ?
H61D C61B H61E . . 109.5 ?
C6B C61B H61F . . 109.5 ?
H61D C61B H61F . . 109.5 ?
H61E C61B H61F . . 109.5 ?
C2X C1X H1X1 . . 109.5 ?
C2X C1X H1X2 . . 109.5 ?
H1X1 C1X H1X2 . . 109.5 ?
C2X C1X H1X3 . . 109.5 ?
H1X1 C1X H1X3 . . 109.5 ?
H1X2 C1X H1X3 . . 109.5 ?
O2X C2X N3X . . 119.1(4) ?
O2X C2X C1X . . 121.4(4) ?
N3X C2X C1X . . 119.5(4) ?
C2X N3X C4X . . 120.5(4) ?
C2X N3X C5X . . 121.4(4) ?
C4X N3X C5X . . 118.1(4) ?
N3X C4X H4X1 . . 109.5 ?
N3X C4X H4X2 . . 109.5 ?
H4X1 C4X H4X2 . . 109.5 ?
N3X C4X H4X3 . . 109.5 ?
H4X1 C4X H4X3 . . 109.5 ?
H4X2 C4X H4X3 . . 109.5 ?
N3X C5X H5X1 . . 109.5 ?
N3X C5X H5X2 . . 109.5 ?
H5X1 C5X H5X2 . . 109.5 ?
N3X C5X H5X3 . . 109.5 ?
H5X1 C5X H5X3 . . 109.5 ?
H5X2 C5X H5X3 . . 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
N1A C2A . 1.360(5) ?
N1A C6A . 1.370(5) ?
N1A H1A . 0.8800 ?
C2A N3A . 1.329(5) ?
C2A N21A . 1.328(5) ?
N21A H21A . 0.8800 ?
N21A H21B . 0.8800 ?
N3A C4A . 1.380(5) ?
C4A O41A . 1.256(4) ?
C4A C5A . 1.446(5) ?
C5A C6A . 1.351(5) ?
C5A H5A . 0.9500 ?
C6A C61A . 1.481(6) ?
C61A H61A . 0.9800 ?
C61A H61B . 0.9800 ?
C61A H61C . 0.9800 ?
N1B C2B . 1.317(5) ?
N1B C6B . 1.377(5) ?
C2B N21B . 1.336(4) ?
C2B N3B . 1.361(4) ?
N21B H21C . 0.8800 ?
N21B H21D . 0.8800 ?
N3B C4B . 1.377(5) ?
N3B H3B . 0.8800 ?
C4B O41B . 1.247(4) ?
C4B C5B . 1.435(5) ?
C5B C6B . 1.368(5) ?
C5B H5B . 0.9500 ?
C6B C61B . 1.499(5) ?
C61B H61D . 0.9800 ?
C61B H61E . 0.9800 ?
C61B H61F . 0.9800 ?
C1X C2X . 1.503(6) ?
C1X H1X1 . 0.9800 ?
C1X H1X2 . 0.9800 ?
C1X H1X3 . 0.9800 ?
C2X O2X . 1.250(5) ?
C2X N3X . 1.334(5) ?
N3X C4X . 1.456(6) ?
N3X C5X . 1.476(6) ?
C4X H4X1 . 0.9800 ?
C4X H4X2 . 0.9800 ?
C4X H4X3 . 0.9800 ?
C5X H5X1 . 0.9800 ?
C5X H5X2 . 0.9800 ?
C5X H5X3 . 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
N21A H21A O41B . 0.88 1.92 2.803(4) 178
N21A H21B O2X . 0.88 2.06 2.843(4) 147
N1A H1A O2X . 0.88 2.02 2.807(4) 149
N3B H3B N3A . 0.88 1.97 2.844(4) 177
N21B H21C N1B 2_655 0.88 2.10 2.969(4) 172
N21B H21D O41A . 0.88 2.00 2.877(4) 173
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
C6A N1A C2A N3A . . . . -1.7(6) ?
C6A N1A C2A N21A . . . . 178.9(3) ?
N21A C2A N3A C4A . . . . -179.7(3) ?
N1A C2A N3A C4A . . . . 1.0(5) ?
C2A N3A C4A O41A . . . . -179.4(4) ?
C2A N3A C4A C5A . . . . 0.4(5) ?
O41A C4A C5A C6A . . . . 178.7(4) ?
N3A C4A C5A C6A . . . . -1.1(5) ?
C4A C5A C6A N1A . . . . 0.4(5) ?
C4A C5A C6A C61A . . . . -179.6(4) ?
C2A N1A C6A C5A . . . . 0.9(5) ?
C2A N1A C6A C61A . . . . -179.0(4) ?
C6B N1B C2B N21B . . . . -177.8(3) ?
C6B N1B C2B N3B . . . . 0.2(5) ?
N1B C2B N3B C4B . . . . -0.4(5) ?
N21B C2B N3B C4B . . . . 177.6(3) ?
C2B N3B C4B O41B . . . . -179.0(4) ?
C2B N3B C4B C5B . . . . 0.1(5) ?
O41B C4B C5B C6B . . . . 179.4(4) ?
N3B C4B C5B C6B . . . . 0.3(5) ?
C2B N1B C6B C5B . . . . 0.3(5) ?
C2B N1B C6B C61B . . . . 179.5(3) ?
C4B C5B C6B N1B . . . . -0.6(6) ?
C4B C5B C6B C61B . . . . -179.7(4) ?
O2X C2X N3X C4X . . . . -0.5(6) ?
C1X C2X N3X C4X . . . . -179.1(4) ?
O2X C2X N3X C5X . . . . -177.6(4) ?
C1X C2X N3X C5X . . . . 3.8(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654307
