#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:33:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180510 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/79/7217945.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_7217945
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            'C8 H18 N4 O6'
_chemical_formula_weight         266.00
_chemical_name_common
;
 bis(methylurea) succinic acid
;
_chemical_name_systematic
;
 bis(N-methylurea) butanedioic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.22
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.890(5)
_cell_length_b                   5.790(5)
_cell_length_c                   13.650(5)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    20
_cell_volume                     623.4(7)
_computing_cell_refinement       'lauegen (CCP4)'
_computing_data_collection       'VIVALDI (MAATEL)'
_computing_data_reduction        'argonne_boxes, laue4 (Piltz, 2011)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      20
_diffrn_detector_area_resol_mean 0.7
_diffrn_measurement_device_type  VIVALDI
_diffrn_measurement_method       'Laue patterns at 10 orientations'
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'ILL reactor source, thermal guide'
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.80-5.20
_diffrn_reflns_av_R_equivalents  0.1364
_diffrn_reflns_av_sigmaI/netI    0.0854
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13957
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             12
_exptl_crystal_size_max          2.5
_exptl_crystal_size_mid          1.0
_exptl_crystal_size_min          0.8
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.025
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.344
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.344
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0538
_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)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                1945
_reflns_number_total             2522
_reflns_threshold_expression     >2σ(I)
_cod_duplicate_entry             7214480
_cod_data_source_file            c4ce00587b2.cif
_cod_data_source_block           musuc_20
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7217945
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
H2 H 0.4378(3) 0.8230(3) 0.42318(15) 0.0245(4) Uani 1 1 d
H6 H 1.0438(3) -0.0812(3) 0.57778(12) 0.0206(4) Uani 1 1 d
H3 H 0.6174(3) 0.9968(3) 0.41135(16) 0.0258(5) Uani 1 1 d
H5 H 0.8995(3) 0.3171(3) 0.75924(12) 0.0236(4) Uani 1 1 d
H4 H 0.8225(3) 0.5007(3) 0.66713(14) 0.0226(5) Uani 1 1 d
H1 H 0.7828(3) 0.4602(3) 0.49259(13) 0.0188(4) Uani 1 1 d
H9 H 1.1425(5) -0.2020(5) 0.73041(19) 0.0528(10) Uani 1 1 d
H7 H 0.9556(4) -0.0970(6) 0.7756(2) 0.0434(7) Uani 1 1 d
H8 H 1.1314(5) 0.0786(5) 0.77591(19) 0.0511(9) Uani 1 1 d
O2 O 0.67428(14) 0.73391(13) 0.60528(6) 0.0088(2) Uani 1 1 d
O1 O 0.70403(13) 0.57739(14) 0.45700(6) 0.00883(18) Uani 1 1 d
O3 O 0.89466(14) 0.26231(13) 0.52647(6) 0.0090(2) Uani 1 1 d
C2 C 0.53727(11) 0.91292(11) 0.46519(5) 0.00766(16) Uani 1 1 d
N2 N 1.02140(9) 0.02463(8) 0.63597(4) 0.00874(13) Uani 1 1 d
C3 C 0.93379(11) 0.21644(11) 0.61471(5) 0.00647(16) Uani 1 1 d
C1 C 0.64513(12) 0.73338(11) 0.51675(5) 0.00647(16) Uani 1 1 d
C4 C 1.06603(13) -0.05139(13) 0.73411(5) 0.01056(17) Uani 1 1 d
N1 N 0.89040(9) 0.36022(9) 0.68745(4) 0.01043(13) 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
H2 0.0233(12) 0.0231(8) 0.0265(8) -0.0082(6) -0.0095(8) 0.0021(7)
H6 0.0290(12) 0.0175(6) 0.0154(6) -0.0023(5) 0.0003(7) 0.0073(6)
H3 0.0329(16) 0.0243(8) 0.0208(8) 0.0075(5) 0.0119(9) 0.0062(7)
H5 0.0362(13) 0.0237(7) 0.0109(6) 0.0026(5) 0.0010(7) 0.0060(7)
H4 0.0306(14) 0.0185(7) 0.0187(8) 0.0011(5) 0.0027(8) 0.0097(6)
H1 0.0219(11) 0.0181(6) 0.0165(7) -0.0001(5) -0.0001(7) 0.0067(7)
H9 0.081(3) 0.0508(13) 0.0270(10) 0.0079(10) 0.0045(13) 0.0490(16)
H7 0.0332(19) 0.0697(19) 0.0280(11) 0.0199(11) 0.0116(11) 0.0001(13)
H8 0.080(2) 0.0422(13) 0.0300(11) 0.0072(9) -0.0279(13) -0.0253(13)
O2 0.0129(6) 0.0087(3) 0.0047(3) 0.0001(2) 0.0004(3) 0.0036(3)
O1 0.0108(5) 0.0089(3) 0.0067(3) -0.0012(2) -0.0001(3) 0.0041(3)
O3 0.0134(6) 0.0086(3) 0.0052(3) 0.0001(2) -0.0003(4) 0.0041(3)
C2 0.0099(5) 0.0074(2) 0.0057(3) -0.00006(17) -0.0001(3) 0.0026(2)
N2 0.0118(4) 0.00801(17) 0.0064(2) 0.00049(13) -0.0001(2) 0.00332(16)
C3 0.0078(5) 0.0070(2) 0.0047(3) 0.00049(17) 0.0009(3) 0.0011(2)
C1 0.0081(5) 0.0059(2) 0.0054(3) -0.00029(17) 0.0003(3) 0.0017(2)
C4 0.0133(5) 0.0110(3) 0.0074(3) 0.0025(2) 0.0002(3) 0.0024(3)
N1 0.0153(4) 0.00970(19) 0.00631(19) -0.00019(14) 0.0008(2) 0.00391(18)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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 112.91(8) 3_676
C3 N2 C4 124.65(6) .
O3 C3 N2 119.71(7) .
O3 C3 N1 120.79(8) .
N2 C3 N1 119.49(7) .
O2 C1 O1 123.68(8) .
O2 C1 C2 123.42(8) .
O1 C1 C2 112.90(7) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C1 1.2253(11) .
O1 C1 1.3088(12) .
O3 C3 1.2652(11) .
C2 C1 1.5082(12) .
C2 C2 1.5131(16) 3_676
N2 C3 1.3368(12) .
N2 C4 1.4464(10) .
C3 N1 1.3456(10) .
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
O1 H1 O3 1.0342(19) 1.513(2) 2.5355(17) 168.91(17)
N1 H4 O2 1.0095(18) 1.965(2) 2.9606(18) 168.26(16)
