#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/45/7214503.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_7214503
loop_
_publ_author_name
'Jones, Andrew O. F.'
'Leech, Charlotte K.'
'McIntyre, Garry J.'
'Wilson, Chick C.'
'Thomas, Lynne H.'
_publ_section_title
;
 Engineering short, strong hydrogen bonds in urea di-carboxylic acid
 complexes
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              8177
_journal_paper_doi               10.1039/C4CE00587B
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C6 H14 N4 O6'
_chemical_formula_weight         238.21
_chemical_name_common
;
 bis(urea) succinic acid
;
_chemical_name_systematic
;
 bis(urea) butanedioic acid
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-03-19 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.160(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.7109(7)
_cell_length_b                   7.9698(11)
_cell_length_c                   12.1580(15)
_cell_measurement_reflns_used    5241
_cell_measurement_temperature    100
_cell_measurement_theta_max      55.20
_cell_measurement_theta_min      6.12
_cell_volume                     550.17(12)
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
'Rigaku R-AXIS RAPID IP Image Plate diffractometer'
;
_diffrn_measurement_method       'Image plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7014
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.0856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                1085
_reflns_number_total             1255
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ce00587b2.cif
_cod_data_source_block           u_suc_100k
_cod_depositor_comments
'Adding full bibliography for 7214477--7214509.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7214503
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_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
H2 H 0.972(2) 0.6183(17) 0.4122(11) 0.027(3) Uiso 1 1 d
H7 H -0.040(2) 0.4498(18) 0.1036(12) 0.031(3) Uiso 1 1 d
H3 H 0.819(2) 0.4593(17) 0.4134(11) 0.027(3) Uiso 1 1 d
H6 H 0.073(2) 0.4386(18) 0.2245(12) 0.031(3) Uiso 1 1 d
H4 H 0.525(3) 0.686(2) 0.1934(12) 0.038(4) Uiso 1 1 d
H1 H 0.449(3) 0.769(2) 0.4940(15) 0.059(5) Uiso 1 1 d
H5 H 0.408(3) 0.586(2) 0.2808(13) 0.041(4) Uiso 1 1 d
O1 O 0.74389(13) 0.64935(9) 0.62142(6) 0.0236(2) Uani 1 1 d
O3 O 0.24781(13) 0.62748(9) 0.03413(6) 0.0239(2) Uani 1 1 d
O2 O 0.56110(13) 0.70458(10) 0.45368(6) 0.0239(2) Uani 1 1 d
C2 C 0.90456(17) 0.54109(13) 0.46101(8) 0.0199(2) Uani 1 1 d
N2 N 0.06554(16) 0.47996(12) 0.15811(8) 0.0230(2) Uani 1 1 d
C1 C 0.73060(17) 0.63713(12) 0.52082(8) 0.0186(2) Uani 1 1 d
C3 C 0.24276(18) 0.57580(13) 0.13201(8) 0.0211(2) Uani 1 1 d
N1 N 0.41197(19) 0.61823(15) 0.21203(8) 0.0335(3) Uani 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0258(4) 0.0287(4) 0.0160(4) 0.0007(3) 0.0010(3) 0.0057(3)
O3 0.0261(4) 0.0285(4) 0.0161(4) 0.0036(3) -0.0018(3) -0.0077(3)
O2 0.0258(4) 0.0282(4) 0.0167(4) -0.0013(3) -0.0015(3) 0.0087(3)
C2 0.0217(5) 0.0210(5) 0.0169(5) -0.0001(4) 0.0015(4) 0.0020(4)
N2 0.0244(5) 0.0273(5) 0.0167(4) 0.0041(3) -0.0005(4) -0.0048(4)
C1 0.0204(5) 0.0175(5) 0.0175(5) 0.0013(4) 0.0007(4) -0.0013(4)
C3 0.0240(5) 0.0215(5) 0.0172(5) -0.0001(4) 0.0002(4) -0.0003(4)
N1 0.0362(6) 0.0453(6) 0.0173(5) 0.0074(4) -0.0049(4) -0.0194(5)
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
_geom_angle_site_symmetry_3
C1 C2 C2 112.72(10) 3_766
O1 C1 O2 123.55(9) .
O1 C1 C2 123.52(9) .
O2 C1 C2 112.92(8) .
O3 C3 N2 120.40(9) .
O3 C3 N1 120.99(10) .
N2 C3 N1 118.61(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2212(12) .
O3 C3 1.2625(12) .
O2 C1 1.3125(12) .
C2 C1 1.5022(14) .
C2 C2 1.5148(19) 3_766
N2 C3 1.3332(14) .
C3 N1 1.3390(14) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H1 O3 0.990(18) 1.536(19) 2.5149(10) 168.7(16) 4_576
N1 H4 O1 0.887(16) 2.072(16) 2.9473(13) 168.6(13) 4_575
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139063296
