#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:33:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180510 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/79/7217953.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_7217953
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 H16 N4 O6'
_chemical_formula_weight         264.25
_chemical_name_common
;
 bis(methylurea) fumaric acid
;
_chemical_name_systematic
;
 bis(N-methylurea) trans-butenedioic 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                 102.959(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5509(16)
_cell_length_b                   5.5691(8)
_cell_length_c                   13.909(2)
_cell_measurement_reflns_used    4754
_cell_measurement_temperature    200
_cell_measurement_theta_max      55.06
_cell_measurement_theta_min      6.01
_cell_volume                     645.49(18)
_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      200
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     0.71075
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8540
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0398
_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)+(0.0530P)²+0.0178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                1002
_reflns_number_total             1475
_reflns_threshold_expression     >2σ(I)
_cod_duplicate_entry             7214488
_cod_data_source_file            c4ce00587b2.cif
_cod_data_source_block           mu_fum_200k
_cod_original_cell_volume        645.47(18)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7217953
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
H8 H 0.973(3) -0.188(4) 0.7570(15) 0.083(7) Uiso 1 1 d
H3 H 0.892(2) 0.231(3) 0.7499(14) 0.053(5) Uiso 1 1 d
H1 H 0.933(2) 0.493(3) 1.0856(13) 0.056(5) Uiso 1 1 d
H5 H 1.047(2) -0.081(3) 0.5896(14) 0.054(5) Uiso 1 1 d
H6 H 1.128(3) -0.264(4) 0.7267(16) 0.094(8) Uiso 1 1 d
H2 H 0.709(3) -0.014(4) 0.9968(17) 0.094(7) Uiso 1 1 d
H4 H 0.805(2) 0.403(4) 0.6710(13) 0.058(5) Uiso 1 1 d
H7 H 1.118(3) -0.006(4) 0.7800(17) 0.095(8) Uiso 1 1 d
O1 O 0.86053(14) 0.1577(2) 0.89369(8) 0.0526(4) Uani 1 1 d
O2 O 0.76953(13) 0.1333(2) 1.03222(7) 0.0469(3) Uani 1 1 d
O3 O 0.88245(13) 0.25173(18) 0.52791(7) 0.0469(3) Uani 1 1 d
N1 N 1.01672(17) -0.0192(3) 0.63556(10) 0.0475(4) Uani 1 1 d
C3 C 0.92295(18) 0.1739(3) 0.61530(10) 0.0391(4) Uani 1 1 d
C2 C 0.94902(18) 0.4434(3) 1.02129(11) 0.0410(4) Uani 1 1 d
N2 N 0.8721(2) 0.2828(3) 0.68834(11) 0.0524(4) Uani 1 1 d
C4 C 1.0673(3) -0.1267(4) 0.73203(14) 0.0584(5) Uani 1 1 d
C1 C 0.85581(18) 0.2316(3) 0.97604(10) 0.0390(4) 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 0.0673(8) 0.0590(7) 0.0366(6) -0.0055(5) 0.0225(5) -0.0169(6)
O2 0.0536(7) 0.0557(7) 0.0343(6) -0.0012(5) 0.0163(5) -0.0155(5)
O3 0.0556(7) 0.0553(7) 0.0323(6) 0.0035(5) 0.0154(5) 0.0163(6)
N1 0.0593(9) 0.0520(8) 0.0353(8) 0.0032(6) 0.0192(7) 0.0139(7)
C3 0.0428(8) 0.0436(8) 0.0336(8) -0.0020(7) 0.0143(6) -0.0015(7)
C2 0.0451(9) 0.0463(9) 0.0327(8) 0.0007(7) 0.0108(6) -0.0005(7)
N2 0.0738(11) 0.0533(9) 0.0344(8) 0.0030(7) 0.0209(7) 0.0168(8)
C4 0.0757(13) 0.0591(12) 0.0431(10) 0.0119(9) 0.0191(9) 0.0141(11)
C1 0.0400(8) 0.0456(8) 0.0325(8) 0.0048(7) 0.0103(6) -0.0001(7)
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_1
C3 N1 C4 124.86(15) .
O3 C3 N1 120.15(13) .
O3 C3 N2 120.62(15) .
N1 C3 N2 119.23(14) .
C2 C2 C1 122.42(19) 3_767
O1 C1 O2 123.95(14) .
O1 C1 C2 122.43(13) .
O2 C1 C2 113.62(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2262(17) .
O2 C1 1.3088(17) .
O3 C3 1.2636(17) .
N1 C3 1.333(2) .
N1 C4 1.444(2) .
C3 N2 1.337(2) .
C2 C2 1.319(3) 3_767
C2 C1 1.483(2) .
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 H2 O3 1.04(2) 1.52(2) 2.5333(14) 165(2) 2_646
N2 H4 O1 0.88(2) 2.06(2) 2.932(2) 170.1(16) 2_656
