#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:26:48 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180475 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/44/7214493.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_7214493
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            'C10 H22 N4 O6'
_chemical_formula_weight         294.00
_chemical_name_common
;
 bis(N,N-dimethylurea) succinic acid
;
_chemical_name_systematic
;
 bis(N,N-dimethylurea) 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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.400(5)
_cell_length_b                   5.470(5)
_cell_length_c                   15.470(5)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    50
_cell_volume                     695.4(8)
_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      50
_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  0.1203
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9617
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             11
_exptl_crystal_size_max          2.8
_exptl_crystal_size_mid          1.0
_exptl_crystal_size_min          0.8
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.100
_refine_diff_density_rms         0.023
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0473
_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          0.0777
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                1931
_reflns_number_total             2549
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ce00587b2.cif
_cod_data_source_block           dmusuc_50
_cod_depositor_comments
'Adding full bibliography for 7214477--7214509.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7214493
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 0.3909(3) 0.7524(4) 0.77423(12) 0.0234(4) Uani 1 1 d
H10 H 0.3242(2) -0.0160(4) 0.44752(15) 0.0265(4) Uani 1 1 d
H11 H 0.4734(3) 0.1755(4) 0.42067(13) 0.0251(4) Uani 1 1 d
H5 H 0.2632(3) 0.9818(4) 0.82604(14) 0.0306(5) Uani 1 1 d
H6 H -0.0825(3) 1.1710(6) 0.66356(17) 0.0338(5) Uani 1 1 d
H1 H 0.3932(2) 0.5690(4) 0.68330(13) 0.0231(4) Uani 1 1 d
H7 H -0.0138(3) 1.0638(5) 0.57057(15) 0.0393(6) Uani 1 1 d
H8 H 0.0646(3) 1.3357(5) 0.6229(2) 0.0407(6) Uani 1 1 d
H3 H 0.1067(3) 1.1936(6) 0.80227(16) 0.0372(6) Uani 1 1 d
H4 H 0.2950(4) 1.2605(5) 0.77551(16) 0.0399(7) Uani 1 1 d
H9 H 0.2447(2) 0.5617(4) 0.53332(12) 0.0203(3) Uani 1 1 d
O1 O 0.17893(12) 0.76868(18) 0.57837(6) 0.01043(17) Uani 1 1 d
O3 O 0.44579(12) 0.29492(19) 0.61366(6) 0.01089(17) Uani 1 1 d
O2 O 0.27882(11) 0.4307(2) 0.49234(6) 0.01185(17) Uani 1 1 d
C5 C 0.43443(9) 0.08490(15) 0.47595(5) 0.00817(14) Uani 1 1 d
C1 C 0.22446(8) 0.83154(15) 0.65747(5) 0.00732(14) Uani 1 1 d
N2 N 0.14761(7) 1.01297(10) 0.69124(4) 0.00874(11) Uani 1 1 d
N1 N 0.34988(7) 0.71630(12) 0.71003(4) 0.01065(12) Uani 1 1 d
C3 C 0.20710(10) 1.11633(16) 0.77803(5) 0.01030(15) Uani 1 1 d
C4 C 0.38777(10) 0.27952(14) 0.53469(5) 0.00736(14) Uani 1 1 d
C2 C 0.02269(10) 1.15319(17) 0.63335(5) 0.01187(16) Uani 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 0.0000 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
C4 C5 C5 113.07(8) 3_656
O1 C1 N1 120.26(8) .
O1 C1 N2 120.49(7) .
N1 C1 N2 119.24(7) .
C1 N2 C3 123.13(6) .
C1 N2 C2 119.60(7) .
C3 N2 C2 115.67(7) .
O3 C4 O2 123.49(9) .
O3 C4 C5 123.62(8) .
O2 C4 C5 112.89(8) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2522(11) .
O3 C4 1.2209(11) .
O2 C4 1.3049(13) .
C5 C4 1.5033(14) .
C5 C5 1.5134(16) 3_656
C1 N1 1.3468(10) .
C1 N2 1.3469(12) .
N2 C3 1.4473(10) .
N2 C2 1.4498(11) .
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
O2 H9 O1 1.036(2) 1.494(2) 2.5209(19) 170.30(18)
N1 H1 O3 1.007(2) 1.949(2) 2.947(2) 169.85(16)
