#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/48/4504805.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_4504805
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 H11 N4 O, C4 H5 O4'
_chemical_formula_sum            'C15 H16 N4 O5'
_chemical_formula_weight         332.32
_chemical_melting_point          452
_chemical_name_common            N,N'-bis(3-pyridyl)urea+succinicacid
_chemical_name_systematic
; 
 N,N'-bis(3-pyridyl)urea+succinicacid 
;
_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                 109.35(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   38.093(8)
_cell_length_b                   5.2820(11)
_cell_length_c                   16.428(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     3118.7(12)
_computing_cell_refinement       'CAD4 data collection software'
_computing_data_collection       'CAD4 data collection software'
_computing_data_reduction        'WinGx Version 1.64.05'
_computing_molecular_graphics    'PLUTON (Spek, 1992)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius -MACH3'
_diffrn_measurement_method       'ω 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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3606
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.13
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.322
_refine_ls_extinction_coef       0.033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0676
_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)+(0.1241P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.2028
_reflns_number_gt                2369
_reflns_number_total             3565
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0580152_dipyurea_3_succinic_acid.cif
_cod_data_source_block           mdpu.sa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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_cell_volume        3118.7(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4504805
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
H5A H 0.0562(10) -0.077(8) 0.037(3) 0.106(13) Uiso 1 1 d .
H4A H 0.3206(8) 0.589(6) 0.1598(18) 0.058(8) Uiso 1 1 d .
H3A H 0.3762(7) 0.647(5) 0.2170(16) 0.047(7) Uiso 1 1 d .
H2A H 0.1975(10) 0.468(7) 0.003(2) 0.095(11) Uiso 1 1 d .
N2 N 0.21604(5) 0.6363(4) 0.06047(12) 0.0433(5) Uani 1 1 d .
N4 N 0.31351(5) 0.7143(4) 0.18486(13) 0.0445(5) Uani 1 1 d .
N3 N 0.37537(5) 0.7796(4) 0.24784(13) 0.0470(5) Uani 1 1 d .
O1 O 0.33408(5) 1.0276(4) 0.28494(14) 0.0737(7) Uani 1 1 d .
C9 C 0.27562(6) 0.7675(4) 0.15464(13) 0.0388(5) Uani 1 1 d .
C10 C 0.25276(6) 0.6022(4) 0.09417(14) 0.0402(5) Uani 1 1 d .
H10 H 0.2634 0.4632 0.0766 0.048 Uiso 1 1 calc R
N1 N 0.44573(6) 1.1895(4) 0.39664(15) 0.0550(6) Uani 1 1 d .
C11 C 0.34061(6) 0.8565(5) 0.24287(14) 0.0445(5) Uani 1 1 d .
C4 C 0.40929(6) 0.8873(4) 0.29676(14) 0.0425(5) Uani 1 1 d .
C8 C 0.25904(6) 0.9741(4) 0.17980(15) 0.0461(5) Uani 1 1 d .
H8 H 0.2733 1.0898 0.2198 0.055 Uiso 1 1 calc R
C7 C 0.22099(7) 1.0042(4) 0.14426(16) 0.0472(6) Uani 1 1 d .
H7 H 0.2095 1.1413 0.1605 0.057 Uiso 1 1 calc R
C5 C 0.41271(6) 1.0946(5) 0.35042(16) 0.0477(6) Uani 1 1 d .
H5 H 0.3913 1.1702 0.3543 0.057 Uiso 1 1 calc R
C6 C 0.20012(6) 0.8333(4) 0.08528(15) 0.0453(5) Uani 1 1 d .
H6 H 0.1745 0.8549 0.0622 0.054 Uiso 1 1 calc R
C3 C 0.44134(7) 0.7787(6) 0.29147(19) 0.0611(7) Uani 1 1 d .
H3 H 0.4400 0.6393 0.2560 0.073 Uiso 1 1 calc R
C1 C 0.47651(7) 1.0835(6) 0.3901(2) 0.0646(8) Uani 1 1 d .
H1 H 0.4995 1.1521 0.4215 0.078 Uiso 1 1 calc R
C2 C 0.47535(7) 0.8782(7) 0.3391(2) 0.0745(9) Uani 1 1 d .
H2 H 0.4972 0.8062 0.3366 0.089 Uiso 1 1 calc R
O3 O 0.18348(5) 0.3090(3) -0.05514(12) 0.0531(5) Uani 1 1 d .
O5 O 0.05251(5) 0.0521(4) -0.00855(14) 0.0673(6) Uani 1 1 d .
O2 O 0.13292(6) 0.1098(4) -0.12991(14) 0.0700(6) Uani 1 1 d .
O4 O 0.11381(5) 0.0344(4) 0.04838(13) 0.0659(6) Uani 1 1 d .
C12 C 0.14809(7) 0.2759(4) -0.07821(14) 0.0441(5) Uani 1 1 d .
C15 C 0.08625(6) 0.1304(5) 0.00036(16) 0.0456(5) Uani 1 1 d .
C13 C 0.12584(6) 0.4489(4) -0.04186(15) 0.0449(5) Uani 1 1 d .
H13A H 0.1246 0.6145 -0.0682 0.054 Uiso 1 1 calc R
H13B H 0.1386 0.4681 0.0196 0.054 Uiso 1 1 calc R
C14 C 0.08675(6) 0.3563(5) -0.05591(16) 0.0489(6) Uani 1 1 d .
H14A H 0.0752 0.3098 -0.1160 0.059 Uiso 1 1 calc R
H14B H 0.0723 0.4923 -0.0432 0.059 Uiso 1 1 calc R
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
C6 N2 C10 119.9(2)
C6 N2 H2A 123.7(15)
C10 N2 H2A 116.4(15)
C11 N4 C9 126.1(2)
C11 N4 H4A 117.9(19)
C9 N4 H4A 115.6(19)
C11 N3 C4 127.5(2)
C11 N3 H3A 115.3(16)
C4 N3 H3A 117.2(16)
N4 C9 C10 117.3(2)
N4 C9 C8 124.9(2)
C10 C9 C8 117.8(2)
N2 C10 C9 122.2(2)
N2 C10 H10 118.9
C9 C10 H10 118.9
C5 N1 C1 119.0(2)
O1 C11 N3 124.6(2)
O1 C11 N4 123.7(2)
N3 C11 N4 111.8(2)
C3 C4 C5 118.1(2)
C3 C4 N3 117.7(2)
C5 C4 N3 124.2(2)
C7 C8 C9 118.8(2)
C7 C8 H8 120.6
C9 C8 H8 120.6
C6 C7 C8 120.4(2)
C6 C7 H7 119.8
C8 C7 H7 119.8
N1 C5 C4 122.1(2)
N1 C5 H5 118.9
C4 C5 H5 118.9
N2 C6 C7 120.9(2)
N2 C6 H6 119.5
C7 C6 H6 119.5
C2 C3 C4 119.5(2)
C2 C3 H3 120.3
C4 C3 H3 120.3
N1 C1 C2 122.2(2)
N1 C1 H1 118.9
C2 C1 H1 118.9
C1 C2 C3 119.1(3)
C1 C2 H2 120.5
C3 C2 H2 120.5
C12 O3 H2A 117.3(16)
C15 O5 H5A 104(2)
O2 C12 O3 120.6(2)
O2 C12 C13 121.0(2)
O3 C12 C13 118.4(2)
O4 C15 O5 123.6(2)
O4 C15 C14 123.4(2)
O5 C15 C14 113.02(19)
C12 C13 C14 113.60(19)
C12 C13 H13A 108.8
C14 C13 H13A 108.8
C12 C13 H13B 108.8
C14 C13 H13B 108.8
H13A C13 H13B 107.7
C13 C14 C15 111.93(19)
C13 C14 H14A 109.2
C15 C14 H14A 109.2
C13 C14 H14B 109.2
C15 C14 H14B 109.2
H14A C14 H14B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C6 1.334(3)
N2 C10 1.335(3)
N2 H2A 1.32(4)
N4 C11 1.373(3)
N4 C9 1.390(3)
N4 H4A 0.87(3)
N3 C11 1.361(3)
N3 C4 1.397(3)
N3 H3A 0.87(3)
O1 C11 1.212(3)
C9 C10 1.391(3)
C9 C8 1.391(3)
C10 H10 0.9300
N1 C5 1.333(3)
N1 C1 1.335(4)
C4 C3 1.378(3)
C4 C5 1.385(3)
C8 C7 1.381(3)
C8 H8 0.9300
C7 C6 1.369(3)
C7 H7 0.9300
C5 H5 0.9300
C6 H6 0.9300
C3 C2 1.377(4)
C3 H3 0.9300
C1 C2 1.362(4)
C1 H1 0.9300
C2 H2 0.9300
O3 C12 1.286(3)
O3 H2A 1.25(4)
O5 C15 1.311(3)
O5 H5A 0.98(4)
O2 C12 1.224(3)
O4 C15 1.197(3)
C12 C13 1.498(3)
C15 C14 1.513(3)
C13 C14 1.511(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9700
C14 H14B 0.9700
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661477
2 PubChem 86084641
