#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/74/2017406.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_2017406
loop_
_publ_author_name
'Orozco, Fabían'
'Insuasty, Braulio'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 A hydrogen-bonded ribbon in
 6-amino-3-methyl-5-nitroso-2-(pyrrolidin-1-yl)pyrimidin-4(3H)-one
 monohydrate and hydrogen-bonded sheets in
 6-amino-2-dimethylamino-3-methyl-5-nitrosopyrimidin-4(3H)-one
 monohydrate
;
_journal_coeditor_code           SK3349
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o549
_journal_page_last               o552
_journal_paper_doi               10.1107/S0108270109039018
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C9 H13 N5 O2 , H2 O'
_chemical_formula_moiety         'C9 H13 N5 O2 , H2 O'
_chemical_formula_sum            'C9 H15 N5 O3'
_chemical_formula_weight         241.26
_chemical_name_systematic
;
6-amino-3-methyl-5-nitroso-2-(pyrrolidin-1- yl)pyrimidin-4(3H)-one
monohydrate
;
_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
_cell_angle_alpha                75.158(9)
_cell_angle_beta                 84.727(7)
_cell_angle_gamma                64.436(16)
_cell_formula_units_Z            2
_cell_length_a                   7.9734(18)
_cell_length_b                   8.452(2)
_cell_length_c                   8.9099(2)
_cell_measurement_reflns_used    2051
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      2.75
_cell_volume                     523.48(19)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Nonius, 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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12137
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            red-violet
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0648
_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
'w = 1/[σ²(Fo²)+(0.0570P)²+0.2677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                1629
_reflns_number_total             2051
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3349.cif
_cod_data_source_block           I
_cod_original_cell_volume        523.46(19)
_cod_database_code               2017406
_cod_database_fobs_code          2017406
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 N1 0.2670(2) 0.3989(2) 0.54705(17) 0.0150(4) Uani d . 1 . .
C C2 0.2106(2) 0.3906(2) 0.4150(2) 0.0137(4) Uani d . 1 . .
N N3 0.1887(2) 0.2428(2) 0.39906(17) 0.0150(4) Uani d . 1 . .
C C4 0.2614(3) 0.0779(2) 0.5103(2) 0.0152(4) Uani d . 1 . .
C C5 0.3364(3) 0.0822(2) 0.6502(2) 0.0157(4) Uani d . 1 . .
C C6 0.3239(3) 0.2514(2) 0.6648(2) 0.0153(4) Uani d . 1 . .
C C31 0.0700(3) 0.2525(3) 0.2780(2) 0.0199(4) Uani d . 1 . .
H H31A -0.0271 0.3760 0.2462 0.030 Uiso calc R 1 . .
H H31B 0.0122 0.1690 0.3186 0.030 Uiso calc R 1 . .
H H31C 0.1453 0.2190 0.1884 0.030 Uiso calc R 1 . .
O O4 0.2530(2) -0.05311(18) 0.48645(15) 0.0223(3) Uani d . 1 . .
N N5 0.4112(2) -0.0779(2) 0.75216(18) 0.0187(4) Uani d . 1 . .
O O5 0.4785(2) -0.08538(18) 0.87926(15) 0.0243(4) Uani d . 1 . .
N N6 0.3725(2) 0.2663(2) 0.79564(17) 0.0189(4) Uani d . 1 . .
H H6B 0.3669 0.3703 0.8031 0.023 Uiso calc R 1 . .
H H6A 0.4107 0.1723 0.8758 0.023 Uiso calc R 1 . .
N N21 0.1696(2) 0.5355(2) 0.29804(16) 0.0153(4) Uani d . 1 . .
C C22 0.1742(3) 0.5409(3) 0.1302(2) 0.0186(4) Uani d . 1 . .
H H22A 0.0517 0.5621 0.0919 0.022 Uiso calc R 1 . .
H H22B 0.2698 0.4266 0.1091 0.022 Uiso calc R 1 . .
C C23 0.2225(3) 0.6978(3) 0.0555(2) 0.0198(4) Uani d . 1 . .
H H23A 0.1673 0.7567 -0.0506 0.024 Uiso calc R 1 . .
H H23B 0.3588 0.6575 0.0500 0.024 Uiso calc R 1 . .
C C24 0.1381(3) 0.8246(3) 0.1626(2) 0.0205(4) Uani d . 1 . .
H H24A 0.0021 0.8935 0.1448 0.025 Uiso calc R 1 . .
H H24B 0.1956 0.9103 0.1489 0.025 Uiso calc R 1 . .
C C25 0.1839(3) 0.6955(2) 0.3222(2) 0.0169(4) Uani d . 1 . .
H H25A 0.3109 0.6647 0.3573 0.020 Uiso calc R 1 . .
H H25B 0.0937 0.7480 0.3997 0.020 Uiso calc R 1 . .
O O41 0.39271(19) -0.39899(18) 0.72240(15) 0.0216(3) Uani d . 1 . .
H H41A 0.3933 -0.3005 0.7318 0.032 Uiso d R 1 . .
H H41B 0.3505 -0.3738 0.6298 0.032 Uiso d 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
C2 N1 C6 . . 118.95(16) ?
N21 C2 N1 . . 116.65(16) ?
N21 C2 N3 . . 120.68(16) ?
N1 C2 N3 . . 122.64(16) ?
C2 N3 C4 . . 121.34(15) ?
C2 N3 C31 . . 122.82(15) ?
C4 N3 C31 . . 115.39(15) ?
O4 C4 N3 . . 119.54(16) ?
O4 C4 C5 . . 125.16(17) ?
N3 C4 C5 . . 115.27(16) ?
N5 C5 C6 . . 127.53(17) ?
N5 C5 C4 . . 114.27(16) ?
C6 C5 C4 . . 118.20(16) ?
N6 C6 N1 . . 117.27(17) ?
N6 C6 C5 . . 120.51(17) ?
N1 C6 C5 . . 122.20(16) ?
N3 C31 H31A . . 109.5 ?
N3 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
N3 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
O5 N5 C5 . . 118.24(16) ?
C6 N6 H6B . . 120.0 ?
C6 N6 H6A . . 120.0 ?
H6B N6 H6A . . 120.0 ?
C2 N21 C25 . . 119.18(15) ?
C2 N21 C22 . . 126.77(15) ?
C25 N21 C22 . . 110.46(14) ?
N21 C22 C23 . . 103.59(15) ?
N21 C22 H22A . . 111.0 ?
C23 C22 H22A . . 111.0 ?
N21 C22 H22B . . 111.0 ?
C23 C22 H22B . . 111.0 ?
H22A C22 H22B . . 109.0 ?
C22 C23 C24 . . 103.53(15) ?
C22 C23 H23A . . 111.1 ?
C24 C23 H23A . . 111.1 ?
C22 C23 H23B . . 111.1 ?
C24 C23 H23B . . 111.1 ?
H23A C23 H23B . . 109.0 ?
C23 C24 C25 . . 102.45(15) ?
C23 C24 H24A . . 111.3 ?
C25 C24 H24A . . 111.3 ?
C23 C24 H24B . . 111.3 ?
C25 C24 H24B . . 111.3 ?
H24A C24 H24B . . 109.2 ?
N21 C25 C24 . . 103.29(15) ?
N21 C25 H25A . . 111.1 ?
C24 C25 H25A . . 111.1 ?
N21 C25 H25B . . 111.1 ?
C24 C25 H25B . . 111.1 ?
H25A C25 H25B . . 109.1 ?
H41A O41 H41B . . 104.8 ?
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 . 1.326(2) ?
N1 C6 . 1.338(2) ?
C2 N21 . 1.325(2) ?
C2 N3 . 1.376(2) ?
N3 C4 . 1.401(2) ?
N3 C31 . 1.463(2) ?
C4 O4 . 1.209(2) ?
C4 C5 . 1.446(3) ?
C5 N5 . 1.336(2) ?
C5 C6 . 1.429(3) ?
C6 N6 . 1.313(2) ?
C31 H31A . 0.9800 ?
C31 H31B . 0.9800 ?
C31 H31C . 0.9800 ?
N5 O5 . 1.273(2) ?
N6 H6B . 0.8800 ?
N6 H6A . 0.8800 ?
N21 C25 . 1.475(2) ?
N21 C22 . 1.482(2) ?
C22 C23 . 1.514(3) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 C24 . 1.516(3) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 C25 . 1.518(3) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
O41 H41A . 0.8600 ?
O41 H41B . 0.8600 ?
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
N6 H6A O5 . 0.88 2.00 2.630(2) 128 no
N6 H6A O5 2_657 0.88 2.25 2.989(2) 142 no
N6 H6B O41 1_565 0.88 1.99 2.808(2) 154 no
O41 H41A N5 . 0.86 2.00 2.860(2) 177 no
O41 H41B O4 . 0.86 2.48 2.946(2) 114 no
O41 H41B N1 1_545 0.86 2.57 3.082(2) 119 no
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 . . . . -174.82(16) ?
C6 N1 C2 N3 . . . . 7.2(3) ?
N21 C2 N3 C4 . . . . 168.53(16) ?
N1 C2 N3 C4 . . . . -13.6(3) ?
N21 C2 N3 C31 . . . . -19.5(3) ?
N1 C2 N3 C31 . . . . 158.34(17) ?
C2 N3 C4 O4 . . . . -173.95(17) ?
C31 N3 C4 O4 . . . . 13.5(2) ?
C2 N3 C4 C5 . . . . 8.1(2) ?
C31 N3 C4 C5 . . . . -164.41(16) ?
O4 C4 C5 N5 . . . . 4.6(3) ?
N3 C4 C5 N5 . . . . -177.62(16) ?
O4 C4 C5 C6 . . . . -175.57(18) ?
N3 C4 C5 C6 . . . . 2.3(2) ?
C2 N1 C6 N6 . . . . -177.61(17) ?
C2 N1 C6 C5 . . . . 3.8(3) ?
N5 C5 C6 N6 . . . . -7.1(3) ?
C4 C5 C6 N6 . . . . 173.03(17) ?
N5 C5 C6 N1 . . . . 171.40(18) ?
C4 C5 C6 N1 . . . . -8.4(3) ?
C6 C5 N5 O5 . . . . 0.9(3) ?
C4 C5 N5 O5 . . . . -179.22(16) ?
N1 C2 N21 C25 . . . . -1.7(2) ?
N3 C2 N21 C25 . . . . 176.31(16) ?
N1 C2 N21 C22 . . . . 154.83(17) ?
N3 C2 N21 C22 . . . . -27.2(3) ?
C2 N21 C22 C23 . . . . -149.59(18) ?
C25 N21 C22 C23 . . . . 8.6(2) ?
N21 C22 C23 C24 . . . . -30.59(19) ?
C22 C23 C24 C25 . . . . 41.04(19) ?
C2 N21 C25 C24 . . . . 176.79(16) ?
C22 N21 C25 C24 . . . . 16.7(2) ?
C23 C24 C25 N21 . . . . -35.16(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654196
