#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/74/2017425.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_2017425
loop_
_publ_author_name
'García, Angélica'
'Insuasty, Braulio'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 4,6-Diamino-2-morpholino-5-nitrosopyrimidine: a polarized molecular
 structure within hydrogen-bonded sheets
;
_journal_coeditor_code           EG3030
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o598
_journal_page_last               o600
_journal_paper_doi               10.1107/S0108270109041122
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H12 N6 O2'
_chemical_formula_moiety         'C8 H12 N6 O2'
_chemical_formula_sum            'C8 H12 N6 O2'
_chemical_formula_weight         224.24
_chemical_name_systematic
;
4,6-Diamino-2-morpholino-5-nitrosopyrimidine
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 110.562(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3340(7)
_cell_length_b                   19.247(3)
_cell_length_c                   8.4472(12)
_cell_measurement_reflns_used    1902
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      3.43
_cell_volume                     964.2(2)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13807
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         3.43
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            red-violet
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.343
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0762P)²+0.7491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1736
_reflns_number_gt                1151
_reflns_number_total             1902
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3030.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017425
_cod_database_fobs_code          2017425
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 0.2606(4) 0.56455(12) 0.5428(3) 0.0240(6) Uani d . 1 . .
C C2 0.4025(5) 0.61254(15) 0.5196(4) 0.0224(7) Uani d . 1 . .
N N3 0.6260(4) 0.61796(13) 0.6027(3) 0.0246(6) Uani d . 1 . .
C C4 0.7193(5) 0.57345(15) 0.7261(4) 0.0235(7) Uani d . 1 . .
C C5 0.5896(5) 0.52000(15) 0.7663(3) 0.0210(7) Uani d . 1 . .
C C6 0.3531(5) 0.51857(15) 0.6657(4) 0.0232(7) Uani d . 1 . .
N N4 0.9360(4) 0.58099(13) 0.8138(3) 0.0281(6) Uani d . 1 . .
H H4A 1.0126 0.6148 0.7890 0.034 Uiso calc R 1 . .
H H4B 1.0039 0.5522 0.8971 0.034 Uiso calc R 1 . .
N N5 0.6995(4) 0.47617(13) 0.8906(3) 0.0267(6) Uani d . 1 . .
O O5 0.5911(3) 0.42688(11) 0.9292(3) 0.0323(6) Uani d . 1 . .
N N6 0.2250(4) 0.47077(13) 0.6953(3) 0.0273(6) Uani d . 1 . .
H H6A 0.0803 0.4693 0.6346 0.033 Uiso calc R 1 . .
H H6B 0.2836 0.4401 0.7761 0.033 Uiso calc R 1 . .
N N21 0.3119(4) 0.66174(13) 0.4029(3) 0.0262(6) Uani d . 1 . .
C C22 0.4502(5) 0.70794(16) 0.3446(4) 0.0289(7) Uani d . 1 . .
H H22A 0.4455 0.6930 0.2312 0.035 Uiso calc R 1 . .
H H22B 0.6086 0.7054 0.4228 0.035 Uiso calc R 1 . .
C C23 0.3685(5) 0.78086(16) 0.3357(4) 0.0298(8) Uani d . 1 . .
H H23A 0.3895 0.7975 0.4511 0.036 Uiso calc R 1 . .
H H23B 0.4589 0.8109 0.2887 0.036 Uiso calc R 1 . .
O O24 0.1358(3) 0.78600(11) 0.2323(3) 0.0293(6) Uani d . 1 . .
C C25 0.0053(5) 0.74386(17) 0.3003(4) 0.0305(8) Uani d . 1 . .
H H25A -0.1558 0.7483 0.2287 0.037 Uiso calc R 1 . .
H H25B 0.0228 0.7609 0.4148 0.037 Uiso calc R 1 . .
C C26 0.0712(5) 0.66843(16) 0.3111(4) 0.0297(8) Uani d . 1 . .
H H26A -0.0134 0.6420 0.3700 0.036 Uiso calc R 1 . .
H H26B 0.0333 0.6490 0.1959 0.036 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
C6 N1 C2 . . 115.7(2) ?
N21 C2 N3 . . 115.4(3) ?
N21 C2 N1 . . 117.1(2) ?
N3 C2 N1 . . 127.5(3) ?
C4 N3 C2 . . 117.4(3) ?
N3 C4 N4 . . 117.5(3) ?
N3 C4 C5 . . 121.3(3) ?
N4 C4 C5 . . 121.2(3) ?
N5 C5 C4 . . 117.1(3) ?
N5 C5 C6 . . 126.8(3) ?
C4 C5 C6 . . 116.1(3) ?
N6 C6 N1 . . 118.9(3) ?
N6 C6 C5 . . 119.2(3) ?
N1 C6 C5 . . 121.9(3) ?
C4 N4 H4A . . 120.0 ?
C4 N4 H4B . . 120.0 ?
H4A N4 H4B . . 120.0 ?
O5 N5 C5 . . 119.4(2) ?
C6 N6 H6A . . 120.0 ?
C6 N6 H6B . . 120.0 ?
H6A N6 H6B . . 120.0 ?
C2 N21 C22 . . 121.9(2) ?
C2 N21 C26 . . 123.5(2) ?
C22 N21 C26 . . 114.2(2) ?
N21 C22 C23 . . 110.8(3) ?
N21 C22 H22A . . 109.5 ?
C23 C22 H22A . . 109.5 ?
N21 C22 H22B . . 109.5 ?
C23 C22 H22B . . 109.5 ?
H22A C22 H22B . . 108.1 ?
O24 C23 C22 . . 111.2(2) ?
O24 C23 H23A . . 109.4 ?
C22 C23 H23A . . 109.4 ?
O24 C23 H23B . . 109.4 ?
C22 C23 H23B . . 109.4 ?
H23A C23 H23B . . 108.0 ?
C25 O24 C23 . . 109.7(2) ?
O24 C25 C26 . . 112.9(3) ?
O24 C25 H25A . . 109.0 ?
C26 C25 H25A . . 109.0 ?
O24 C25 H25B . . 109.0 ?
C26 C25 H25B . . 109.0 ?
H25A C25 H25B . . 107.8 ?
N21 C26 C25 . . 109.6(2) ?
N21 C26 H26A . . 109.8 ?
C25 C26 H26A . . 109.8 ?
N21 C26 H26B . . 109.8 ?
C25 C26 H26B . . 109.8 ?
H26A C26 H26B . . 108.2 ?
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 C2 . 1.350(4) y
C2 N3 . 1.345(3) y
N3 C4 . 1.318(4) y
C4 C5 . 1.430(4) y
C5 C6 . 1.439(4) y
C6 N1 . 1.333(4) y
C2 N21 . 1.342(4) y
C4 N4 . 1.319(4) y
C5 N5 . 1.336(4) y
N5 O5 . 1.278(3) y
C6 N6 . 1.308(4) y
N4 H4A . 0.8800 ?
N4 H4B . 0.8800 ?
N6 H6A . 0.8800 ?
N6 H6B . 0.8800 ?
N21 C22 . 1.450(4) ?
N21 C26 . 1.453(4) ?
C22 C23 . 1.488(4) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 O24 . 1.429(3) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
O24 C25 . 1.416(4) ?
C25 C26 . 1.505(4) ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
C26 H26A . 0.9900 ?
C26 H26B . 0.9900 ?
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
N4 H4A O24 4_676 0.88 2.18 3.040(3) 166 y
N4 H4B O5 3_767 0.88 2.50 3.023(3) 119 y
N4 H4B N5 3_767 0.88 2.16 2.954(4) 149 y
N6 H6A N1 3_566 0.88 2.25 3.102(4) 163 y
N6 H6B O5 . 0.88 1.94 2.603(3) 131 y
C23 H23B N3 4_575 0.99 2.58 3.547(4) 167 y
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
C6 N1 C2 N21 . . . . -176.5(3) ?
C6 N1 C2 N3 . . . . 2.1(4) ?
N21 C2 N3 C4 . . . . 175.6(3) ?
N1 C2 N3 C4 . . . . -3.0(4) ?
C2 N3 C4 N4 . . . . -176.4(3) ?
C2 N3 C4 C5 . . . . 2.1(4) ?
N3 C4 C5 N5 . . . . 178.4(3) ?
N4 C4 C5 N5 . . . . -3.2(4) ?
N3 C4 C5 C6 . . . . -0.7(4) ?
N4 C4 C5 C6 . . . . 177.8(3) ?
C2 N1 C6 N6 . . . . 179.8(3) ?
C2 N1 C6 C5 . . . . -0.4(4) ?
N5 C5 C6 N6 . . . . 0.7(4) ?
C4 C5 C6 N6 . . . . 179.7(3) ?
N5 C5 C6 N1 . . . . -179.2(3) ?
C4 C5 C6 N1 . . . . -0.2(4) ?
C4 C5 N5 O5 . . . . -178.9(2) ?
C6 C5 N5 O5 . . . . 0.0(4) ?
N3 C2 N21 C22 . . . . 12.9(4) ?
N1 C2 N21 C22 . . . . -168.3(3) ?
N3 C2 N21 C26 . . . . -174.2(3) ?
N1 C2 N21 C26 . . . . 4.5(4) ?
C2 N21 C22 C23 . . . . -135.5(3) ?
C26 N21 C22 C23 . . . . 51.0(3) ?
N21 C22 C23 O24 . . . . -55.4(3) ?
C22 C23 O24 C25 . . . . 59.9(3) ?
C23 O24 C25 C26 . . . . -59.6(3) ?
C2 N21 C26 C25 . . . . 137.4(3) ?
C22 N21 C26 C25 . . . . -49.2(3) ?
O24 C25 C26 N21 . . . . 53.6(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654200
