#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/94/2219452.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_2219452
loop_
_publ_author_name
'Djedouani, Amel'
'Boufas, Sihem'
'Allain, Magali'
'Bouet, Gilles'
'Khan, Mustayeen'
_publ_section_title
;
 Zwitterionic
 6-methyl-2-oxo-3-[1-(ureidoiminio)ethyl]-2H-pyran-4-olate
 monohydrate
;
_journal_coeditor_code           WK2091
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1785
_journal_paper_doi               10.1107/S1600536808026032
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C9 H11 N3 O4, H2 O'
_chemical_formula_moiety         'C9 H11 N3 O4, H2 O'
_chemical_formula_structural     'C9 H13 N3 O5'
_chemical_formula_sum            'C9 H13 N3 O5'
_chemical_formula_weight         243.22
_chemical_name_systematic
;
6-methyl-2-oxo-3-[1-(ureidoiminio)ethyl]-2H-pyran-4-olate monohydrate
;
_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
_cell_angle_beta                 104.603(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1731(4)
_cell_length_b                   12.6590(10)
_cell_length_c                   12.3698(3)
_cell_measurement_reflns_used    2841
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      3.05
_cell_volume                     1086.95(11)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.07
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11787
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0289P)²+0.445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                1699
_reflns_number_total             2485
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wk2091.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2219452
_cod_database_fobs_code          2219452
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
C C1 0.5343(3) -0.25527(15) 0.37044(14) 0.0287(4) Uani d . 1
C C2 0.7633(2) -0.06094(14) 0.56842(14) 0.0253(4) Uani d . 1
C C3 0.8032(4) -0.11552(17) 0.67854(16) 0.0476(6) Uani d . 1
H H3A 0.7151 -0.1734 0.6744 0.057 Uiso calc R 1
H H3B 0.7871 -0.0666 0.7348 0.057 Uiso calc R 1
H H3C 0.9329 -0.1418 0.6974 0.057 Uiso calc R 1
C C4 0.8087(2) 0.04894(13) 0.55327(13) 0.0240(4) Uani d . 1
C C5 0.9088(3) 0.11044(14) 0.64744(15) 0.0292(4) Uani d . 1
C C6 0.8929(3) 0.26084(15) 0.52451(15) 0.0305(4) Uani d . 1
C C7 0.8054(3) 0.20520(15) 0.43545(15) 0.0316(4) Uani d . 1
H H7 0.7733 0.2375 0.3657 0.038 Uiso calc R 1
C C8 0.7593(2) 0.09564(14) 0.44518(14) 0.0269(4) Uani d . 1
C C9 0.9441(3) 0.37503(16) 0.52619(18) 0.0422(5) Uani d . 1
H H9A 0.9024 0.4034 0.452 0.051 Uiso calc R 1
H H9B 1.0812 0.3829 0.5527 0.051 Uiso calc R 1
H H9C 0.8817 0.4123 0.5749 0.051 Uiso calc R 1
N N1 0.4877(3) -0.35801(14) 0.36960(16) 0.0397(4) Uani d . 1
N N2 0.6282(2) -0.21693(12) 0.47382(13) 0.0336(4) Uani d . 1
N N3 0.6811(2) -0.11234(12) 0.47752(12) 0.0272(3) Uani d . 1
O O1 0.9689(2) 0.08309(11) 0.74427(10) 0.0424(4) Uani d . 1
O O3 0.6744(2) 0.04451(10) 0.35702(10) 0.0369(4) Uani d . 1
O O2 0.9464(2) 0.21590(10) 0.62831(10) 0.0355(3) Uani d . 1
O O4 0.4983(2) -0.19779(11) 0.28793(11) 0.0414(4) Uani d . 1
O O1W 0.6521(3) -0.10956(13) 0.12207(12) 0.0470(4) Uani d D 1
H H11W 0.597(4) -0.131(2) 0.168(2) 0.071 Uiso d D 1
H H21W 0.763(4) -0.103(2) 0.160(2) 0.071 Uiso d D 1
H H1A 0.440(3) -0.3872(19) 0.308(2) 0.048(7) Uiso d . 1
H H1B 0.514(3) -0.3924(17) 0.4326(19) 0.037(6) Uiso d . 1
H H2 0.650(3) -0.2591(18) 0.5351(19) 0.042(6) Uiso d . 1
H H3 0.656(4) -0.069(2) 0.410(2) 0.075(8) Uiso 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 0 '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 0.006 '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
O4 C1 N1 124.65(17)
O4 C1 N2 121.02(17)
N1 C1 N2 114.33(16)
N3 C2 C4 115.73(15)
N3 C2 C3 119.87(17)
C4 C2 C3 124.41(16)
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C8 C4 C5 119.53(16)
C8 C4 C2 120.58(15)
C5 C4 C2 119.87(15)
O1 C5 O2 113.83(16)
O1 C5 C4 128.74(18)
O2 C5 C4 117.43(15)
C7 C6 O2 121.43(17)
C7 C6 C9 126.21(18)
O2 C6 C9 112.36(16)
C6 C7 C8 120.93(17)
C6 C7 H7 119.5
C8 C7 H7 119.5
O3 C8 C4 122.81(16)
O3 C8 C7 119.05(15)
C4 C8 C7 118.13(15)
C6 C9 H9A 109.5
C6 C9 H9B 109.5
H9A C9 H9B 109.5
C6 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C1 N1 H1A 118.7(16)
C1 N1 H1B 118.7(14)
H1A N1 H1B 122(2)
N3 N2 C1 115.93(15)
N3 N2 H2 123.4(14)
C1 N2 H2 120.7(14)
C2 N3 N2 124.75(15)
C2 N3 H3 113.8(17)
N2 N3 H3 121.4(17)
C6 O2 C5 122.49(14)
H11W O1W H21W 102(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O4 1.227(2) ?
C1 N1 1.342(2) ?
C1 N2 1.375(2) ?
C2 N3 1.304(2) y
C2 C4 1.452(2) y
C2 C3 1.489(2) ?
C3 H3A 0.96 ?
C3 H3B 0.96 ?
C3 H3C 0.96 ?
C4 C8 1.423(2) y
C4 C5 1.434(2) ?
C5 O1 1.217(2) ?
C5 O2 1.394(2) ?
C6 C7 1.325(3) ?
C6 O2 1.368(2) ?
C6 C9 1.490(3) ?
C7 C8 1.438(3) ?
C7 H7 0.93 ?
C8 O3 1.282(2) y
C9 H9A 0.96 ?
C9 H9B 0.96 ?
C9 H9C 0.96 ?
N1 H1A 0.84(3) ?
N1 H1B 0.87(2) ?
N2 N3 1.375(2) ?
N2 H2 0.91(2) ?
N3 H3 0.98(3) ?
O1W H11W 0.82(3) ?
O1W H21W 0.82(3) ?
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
N1 H1A O3 2_645 0.84(2) 2.18(2) 3.015(2) 176.3(17)
N1 H1B O1W 4_556 0.87(2) 2.30(2) 3.075(2) 147.9(19)
N2 H2 O1W 4_556 0.91(2) 1.98(2) 2.839(2) 158(2)
N3 H3 O3 1_555 0.98(2) 1.60(3) 2.476(2) 147(2)
O1W H11W O4 1_555 0.82(3) 1.99(3) 2.796(2) 171(3)
O1W H21W O1 3_756 0.82(3) 2.00(3) 2.823(2) 178.0(18)
C3 H3B O1 1_555 0.9600 2.2900 2.812(3) 114.00
C7 H7 O4 2_655 0.9300 2.4900 3.294(2) 145.00
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655607
2 PubChem 139075274
