#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/48/4504806.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4504806
loop_
_publ_author_name
'Reddy, L. Sreenivas'
'Basavoju, Srinivas'
'Vangala, Venu R.'
'Nangia, Ashwini'
_publ_section_title
;
 Hydrogen Bonding in Crystal Structures ofN,N‘-Bis(3-pyridyl)urea.
 Why Is the N−H···O Tape Synthon Absent in
 Diaryl Ureas with Electron-Withdrawing Groups?
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              161
_journal_paper_doi               10.1021/cg0580152
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C11 H10 N4 O3, H2 O'
_chemical_formula_sum            'C11 H12 N4 O4'
_chemical_formula_weight         264.25
_chemical_melting_point          552
_chemical_name_common            'N,N'-bis(3-pyridyl-N-oxide)urea dihydrate'
_chemical_name_systematic
; 
 N,N'-bis(3-pyridyl-N-oxide)urea dihydrate  
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 90.650(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.9686(7)
_cell_length_b                   12.2243(11)
_cell_length_c                   24.538(2)
_cell_measurement_reflns_used    4983
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.67
_cell_measurement_theta_min      3.05
_cell_volume                     2390.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17207
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombus
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0432P)²+1.4997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                1994
_reflns_number_total             2349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0580152_dipyurea_n-oxide_8_hydrate.cif
_cod_data_source_block           an196_1,3-bis(3-pyridyl-N-oxide)urea
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '552K' was changed to '552' - the
value should be numeric and without a unit
designator.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/ c'
_cod_database_code               4504806
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'
'-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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.14407(16) 0.93604(10) 0.03513(5) 0.0503(3) Uani 1 1 d .
O2 O -0.01366(18) 0.63634(11) -0.06968(6) 0.0576(4) Uani 1 1 d .
N3 N 0.05452(17) 0.72332(11) -0.09221(6) 0.0416(4) Uani 1 1 d .
N1 N 0.3086(2) 1.08793(12) 0.02350(6) 0.0467(4) Uani 1 1 d .
N2 N 0.2559(2) 0.97679(13) -0.04798(6) 0.0464(4) Uani 1 1 d .
C6 C 0.1156(2) 0.80215(14) -0.05908(7) 0.0409(4) Uani 1 1 d .
H6 H 0.1083 0.7942 -0.0215 0.049 Uiso 1 1 calc R
N4 N 0.2922(2) 1.11545(14) 0.17166(6) 0.0516(4) Uani 1 1 d .
C2 C 0.1890(2) 0.89457(13) -0.08068(7) 0.0383(4) Uani 1 1 d .
C1 C 0.2290(2) 0.99422(13) 0.00625(7) 0.0399(4) Uani 1 1 d .
O3 O 0.2436(2) 1.05991(14) 0.21459(6) 0.0731(5) Uani 1 1 d .
C4 C 0.1373(3) 0.82152(16) -0.16912(8) 0.0509(5) Uani 1 1 d .
H4 H 0.1443 0.8272 -0.2068 0.061 Uiso 1 1 calc R
C3 C 0.2006(2) 0.90354(15) -0.13684(7) 0.0476(5) Uani 1 1 d .
H3 H 0.2507 0.9645 -0.1524 0.057 Uiso 1 1 calc R
C11 C 0.2729(2) 1.07122(15) 0.12158(7) 0.0467(4) Uani 1 1 d .
H11 H 0.2255 1.0021 0.1177 0.056 Uiso 1 1 calc R
C5 C 0.0636(2) 0.73108(15) -0.14649(7) 0.0473(4) Uani 1 1 d .
H5 H 0.0204 0.6758 -0.1686 0.057 Uiso 1 1 calc R
C7 C 0.3230(2) 1.12817(14) 0.07618(7) 0.0410(4) Uani 1 1 d .
C8 C 0.3944(2) 1.23165(15) 0.08332(8) 0.0494(5) Uani 1 1 d .
H8 H 0.4294 1.2719 0.0534 0.059 Uiso 1 1 calc R
C10 C 0.3611(3) 1.21543(17) 0.17884(9) 0.0579(5) Uani 1 1 d .
H10 H 0.3733 1.2445 0.2137 0.069 Uiso 1 1 calc R
C9 C 0.4123(3) 1.27301(16) 0.13479(9) 0.0563(5) Uani 1 1 d .
H9 H 0.4603 1.3417 0.1397 0.068 Uiso 1 1 calc R
O4 O 0.0000 0.9142(2) 0.2500 0.0831(8) Uani 1 2 d S
O5 O 0.5000 0.9236(3) 0.2500 0.1144(13) Uani 1 2 d S
H1 H 0.369(2) 1.1194(16) -0.0019(8) 0.047(5) Uiso 1 1 d .
H2 H 0.313(2) 1.0201(17) -0.0646(8) 0.049(6) Uiso 1 1 d .
H4A H 0.070(4) 0.959(2) 0.2361(13) 0.111(11) Uiso 1 1 d .
H5A H 0.585(4) 0.969(3) 0.2584(15) 0.140(14) Uiso 1 1 d .
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
O2 N3 C5 120.11(14)
O2 N3 C6 118.13(14)
C5 N3 C6 121.76(15)
C1 N1 C7 128.03(16)
C1 N1 H1 113.5(13)
C7 N1 H1 117.8(13)
C1 N2 C2 127.71(15)
C1 N2 H2 118.9(14)
C2 N2 H2 113.3(14)
N3 C6 C2 120.34(16)
N3 C6 H6 119.8
C2 C6 H6 119.8
O3 N4 C11 119.40(17)
O3 N4 C10 119.06(17)
C11 N4 C10 121.54(17)
C6 C2 C3 118.65(16)
C6 C2 N2 122.14(16)
C3 C2 N2 119.17(15)
O1 C1 N2 124.82(16)
O1 C1 N1 124.50(16)
N2 C1 N1 110.67(15)
C3 C4 C5 120.80(17)
C3 C4 H4 119.6
C5 C4 H4 119.6
C4 C3 C2 119.23(16)
C4 C3 H3 120.4
C2 C3 H3 120.4
N4 C11 C7 120.21(17)
N4 C11 H11 119.9
C7 C11 H11 119.9
N3 C5 C4 119.22(17)
N3 C5 H5 120.4
C4 C5 H5 120.4
C11 C7 N1 123.60(16)
C11 C7 C8 118.54(17)
N1 C7 C8 117.86(16)
C9 C8 C7 119.27(18)
C9 C8 H8 120.4
C7 C8 H8 120.4
N4 C10 C9 119.43(18)
N4 C10 H10 120.3
C9 C10 H10 120.3
C10 C9 C8 121.02(19)
C10 C9 H9 119.5
C8 C9 H9 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2153(19)
O2 N3 1.3185(18)
N3 C5 1.338(2)
N3 C6 1.348(2)
N1 C1 1.374(2)
N1 C7 1.386(2)
N1 H1 0.88(2)
N2 C1 1.367(2)
N2 C2 1.389(2)
N2 H2 0.81(2)
C6 C2 1.381(2)
C6 H6 0.9300
N4 O3 1.315(2)
N4 C11 1.350(2)
N4 C10 1.350(3)
C2 C3 1.387(2)
C4 C3 1.371(3)
C4 C5 1.372(3)
C4 H4 0.9300
C3 H3 0.9300
C11 C7 1.377(3)
C11 H11 0.9300
C5 H5 0.9300
C7 C8 1.397(3)
C8 C9 1.366(3)
C8 H8 0.9300
C10 C9 1.356(3)
C10 H10 0.9300
C9 H9 0.9300
O4 H4A 0.85(3)
O5 H5A 0.90(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145629
