#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:33:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180510 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/79/7217949.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_7217949
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         266.26
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.246(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0244(12)
_cell_length_b                   5.7496(7)
_cell_length_c                   13.735(2)
_cell_measurement_reflns_used    6503
_cell_measurement_temperature    100
_cell_measurement_theta_max      55.15
_cell_measurement_theta_min      7.09
_cell_volume                     633.54(15)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8408
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0334
_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)+(0.0495P)²+0.1257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                1304
_reflns_number_total             1457
_reflns_threshold_expression     >2σ(I)
_cod_duplicate_entry             7214484
_cod_data_source_file            c4ce00587b2.cif
_cod_data_source_block           mu_suc_100k
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7217949
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 0.4552(17) 0.832(3) 0.4273(10) 0.031(3) Uiso 1 1 d
H6 H 1.0420(19) -0.070(3) 0.5865(12) 0.040(4) Uiso 1 1 d
H3 H 0.6067(17) 0.995(2) 0.4199(10) 0.032(3) Uiso 1 1 d
H5 H 0.8959(18) 0.322(3) 0.7487(12) 0.036(4) Uiso 1 1 d
H4 H 0.825(2) 0.481(3) 0.6685(11) 0.040(4) Uiso 1 1 d
H1 H 0.775(2) 0.476(3) 0.4906(15) 0.065(5) Uiso 1 1 d
H9 H 1.131(2) -0.192(4) 0.7273(13) 0.064(5) Uiso 1 1 d
H7 H 0.975(2) -0.097(3) 0.7719(14) 0.063(5) Uiso 1 1 d
H8 H 1.118(2) 0.067(4) 0.7692(15) 0.070(6) Uiso 1 1 d
O2 O 0.66950(10) 0.72962(13) 0.60484(5) 0.0281(2) Uani 1 1 d
O1 O 0.70661(10) 0.58100(14) 0.45621(5) 0.0301(2) Uani 1 1 d
O3 O 0.88902(10) 0.25833(14) 0.52704(5) 0.0300(2) Uani 1 1 d
C2 C 0.53862(13) 0.91426(19) 0.46515(7) 0.0250(2) Uani 1 1 d
N2 N 1.01736(12) 0.02179(17) 0.63567(7) 0.0281(2) Uani 1 1 d
C3 C 0.92938(13) 0.21310(19) 0.61474(8) 0.0252(2) Uani 1 1 d
C1 C 0.64452(12) 0.73350(17) 0.51657(7) 0.0231(2) Uani 1 1 d
C4 C 1.06804(16) -0.0521(2) 0.73263(8) 0.0319(3) Uani 1 1 d
N1 N 0.88551(13) 0.35658(18) 0.68725(7) 0.0319(2) 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
O2 0.0353(4) 0.0286(4) 0.0205(4) 0.0003(3) -0.0009(3) 0.0064(3)
O1 0.0367(4) 0.0316(4) 0.0219(4) -0.0028(3) -0.0033(3) 0.0125(3)
O3 0.0378(4) 0.0310(4) 0.0211(4) -0.0002(3) -0.0014(3) 0.0110(3)
C2 0.0288(5) 0.0262(5) 0.0201(5) -0.0001(4) -0.0014(4) 0.0041(4)
N2 0.0325(5) 0.0293(5) 0.0222(5) 0.0004(4) -0.0008(4) 0.0069(4)
C3 0.0254(5) 0.0269(5) 0.0233(5) 0.0010(4) 0.0001(4) 0.0009(4)
C1 0.0240(5) 0.0234(5) 0.0218(5) 0.0001(4) -0.0001(4) -0.0004(4)
C4 0.0366(6) 0.0340(6) 0.0250(6) 0.0040(5) -0.0013(4) 0.0072(5)
N1 0.0437(5) 0.0310(5) 0.0209(5) 0.0006(4) -0.0006(4) 0.0110(4)
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_676
C3 N2 C4 125.21(10) .
O3 C3 N2 119.79(10) .
O3 C3 N1 120.79(10) .
N2 C3 N1 119.42(10) .
O2 C1 O1 123.85(9) .
O2 C1 C2 123.68(9) .
O1 C1 C2 112.47(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C1 1.2247(13) .
O1 C1 1.3125(13) .
O3 C3 1.2675(13) .
C2 C1 1.5083(14) .
C2 C2 1.516(2) 3_676
N2 C3 1.3350(14) .
N2 C4 1.4477(14) .
C3 N1 1.3460(15) .
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 0.94(2) 1.62(2) 2.5434(11) 166.5(19)
N1 H4 O2 0.899(17) 2.078(18) 2.9666(13) 169.6(14)
