# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_urea_fumarica_100k

_audit_update_record             
;
2011-05-10 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(urea) (E)-butenedioic acid
;
_chemical_name_common            'bis(urea) fumaric acid'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H12 N4 O6'
_chemical_formula_weight         236.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.764(2)
_cell_length_b                   7.640(2)
_cell_length_c                   12.283(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.901(11)
_cell_angle_gamma                90.00
_cell_volume                     537.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3843
_cell_measurement_theta_min      6.68
_cell_measurement_theta_max      55.20

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7754
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6806
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1230
_reflns_number_gt                1024
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0397P)²+0.1015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1230
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55874(15) 0.19524(12) -0.03999(7) 0.0234(2) Uani 1 1 d . . .
O2 O 0.76079(15) 0.16588(12) 0.12585(7) 0.0253(2) Uani 1 1 d . . .
C1 C 0.7351(2) 0.13801(16) 0.02730(10) 0.0206(3) Uani 1 1 d . . .
C2 C 0.9039(2) 0.03159(17) -0.02714(11) 0.0226(3) Uani 1 1 d . . .
O3 O 0.26345(15) 0.38630(12) 0.03419(7) 0.0254(2) Uani 1 1 d . . .
N1 N 0.4185(2) 0.39507(18) 0.21187(10) 0.0334(3) Uani 1 1 d . . .
N2 N 0.07589(19) 0.53919(16) 0.15380(10) 0.0260(3) Uani 1 1 d . . .
C3 C 0.2536(2) 0.43876(17) 0.13110(10) 0.0225(3) Uani 1 1 d . . .
H1 H 0.449(3) 0.271(3) -0.0015(16) 0.062(6) Uiso 1 1 d . . .
H6 H -0.037(3) 0.562(2) 0.0989(14) 0.034(4) Uiso 1 1 d . . .
H2 H 0.869(2) 0.010(2) -0.1028(13) 0.030(4) Uiso 1 1 d . . .
H5 H 0.077(3) 0.582(2) 0.2212(14) 0.036(4) Uiso 1 1 d . . .
H4 H 0.409(3) 0.426(2) 0.2781(15) 0.041(5) Uiso 1 1 d . . .
H3 H 0.534(3) 0.327(2) 0.1955(13) 0.039(4) Uiso 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 0.0225(4) 0.0272(5) 0.0201(5) -0.0006(4) 0.0005(4) 0.0058(4)
O2 0.0247(5) 0.0313(5) 0.0198(5) 0.0000(4) 0.0025(4) 0.0037(4)
C1 0.0202(6) 0.0213(6) 0.0204(6) 0.0027(5) 0.0029(5) -0.0014(5)
C2 0.0236(6) 0.0249(7) 0.0194(6) -0.0003(5) 0.0037(5) -0.0005(5)
O3 0.0258(5) 0.0307(5) 0.0192(5) -0.0043(4) 0.0008(4) 0.0050(4)
N1 0.0350(7) 0.0449(8) 0.0194(6) -0.0054(5) -0.0010(5) 0.0161(6)
N2 0.0230(6) 0.0334(7) 0.0213(6) -0.0061(5) 0.0008(5) 0.0042(5)
C3 0.0235(6) 0.0232(6) 0.0207(6) -0.0016(5) 0.0023(5) -0.0001(5)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3061(16) . ?
O2 C1 1.2204(15) . ?
C1 C2 1.4869(18) . ?
C2 C2 1.315(3) 3_755 ?
O3 C3 1.2637(15) . ?
N1 C3 1.3315(18) . ?
N2 C3 1.3357(18) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 124.17(11) . . ?
O2 C1 C2 122.24(11) . . ?
O1 C1 C2 113.58(11) . . ?
C2 C2 C1 121.99(15) 3_755 . ?
O3 C3 N1 120.89(12) . . ?
O3 C3 N2 120.09(12) . . ?
N1 C3 N2 119.02(12) . . ?

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
O1 H1 O3 1.01(2) 1.49(2) 2.4962(17) 169.3(18) .
N1 H3 O2 0.887(18) 2.055(18) 2.929(2) 168.1(15) .
N2 H5 O2 0.889(17) 2.096(18) 2.9217(18) 154.1(14) 2_655
N2 H6 O3 0.896(17) 2.005(18) 2.8977(19) 174.0(14) 3_565
N1 H4 O2 0.856(18) 2.445(18) 3.1332(19) 137.9(14) 2_655
N1 H4 O1 0.856(18) 2.477(18) 3.1348(19) 134.3(14) 4_566

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 992787'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_urea_fumarica_200k

_audit_update_record             
;
2011-05-11 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(urea) (E)-butenedioic acid
;
_chemical_name_common            'bis(urea) fumaric acid'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H12 N4 O6'
_chemical_formula_weight         236.20

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.671(4)
_cell_length_b                   7.888(5)
_cell_length_c                   12.348(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.719(3)
_cell_angle_gamma                90.00
_cell_volume                     548.6(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    4836
_cell_measurement_theta_min      6.14
_cell_measurement_theta_max      55.06

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9130
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7039
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1253
_reflns_number_gt                923
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0511P)²+0.0269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1253
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56129(16) 0.19850(12) -0.03888(7) 0.0404(3) Uani 1 1 d . . .
O2 O 0.75610(16) 0.15817(12) 0.12661(7) 0.0422(3) Uani 1 1 d . . .
C1 C 0.7354(2) 0.13705(16) 0.02815(10) 0.0328(3) Uani 1 1 d . . .
C2 C 0.9064(2) 0.03513(17) -0.02659(10) 0.0362(3) Uani 1 1 d . . .
O3 O 0.25841(16) 0.38001(12) 0.03598(7) 0.0426(3) Uani 1 1 d . . .
N1 N 0.4128(3) 0.3872(2) 0.21266(10) 0.0584(4) Uani 1 1 d . . .
N2 N 0.0718(2) 0.53196(16) 0.15424(10) 0.0431(3) Uani 1 1 d . . .
C3 C 0.2483(2) 0.43188(17) 0.13198(10) 0.0372(3) Uani 1 1 d . . .
H1 H 0.447(4) 0.270(2) 0.0014(17) 0.083(6) Uiso 1 1 d . . .
H6 H -0.037(3) 0.5580(19) 0.0983(13) 0.045(4) Uiso 1 1 d . . .
H2 H 0.875(3) 0.025(2) -0.1028(14) 0.054(4) Uiso 1 1 d . . .
H5 H 0.072(3) 0.572(2) 0.2197(14) 0.047(4) Uiso 1 1 d . . .
H4 H 0.404(3) 0.420(2) 0.2787(16) 0.063(5) Uiso 1 1 d . . .
H3 H 0.529(3) 0.319(2) 0.1968(16) 0.064(5) Uiso 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 0.0419(5) 0.0502(6) 0.0278(5) -0.0014(4) -0.0017(4) 0.0143(4)
O2 0.0434(5) 0.0558(6) 0.0266(5) 0.0007(4) 0.0006(4) 0.0106(4)
C1 0.0348(6) 0.0347(7) 0.0285(6) 0.0031(5) 0.0018(5) -0.0007(5)
C2 0.0383(7) 0.0418(7) 0.0279(7) 0.0003(5) 0.0020(5) 0.0033(5)
O3 0.0446(6) 0.0531(6) 0.0283(5) -0.0085(4) -0.0032(4) 0.0139(4)
N1 0.0618(8) 0.0813(10) 0.0290(7) -0.0120(6) -0.0072(6) 0.0307(7)
N2 0.0400(6) 0.0561(8) 0.0320(6) -0.0117(5) -0.0009(5) 0.0101(5)
C3 0.0393(7) 0.0428(7) 0.0288(6) -0.0043(5) 0.0004(5) 0.0022(6)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3055(16) . ?
O2 C1 1.2191(15) . ?
C1 C2 1.4820(19) . ?
C2 C2 1.305(3) 3_755 ?
O3 C3 1.2617(16) . ?
N1 C3 1.3303(19) . ?
N2 C3 1.3283(19) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 123.97(12) . . ?
O2 C1 C2 122.50(11) . . ?
O1 C1 C2 113.51(11) . . ?
C2 C2 C1 122.55(16) 3_755 . ?
O3 C3 N2 120.36(12) . . ?
O3 C3 N1 120.83(13) . . ?
N2 C3 N1 118.81(13) . . ?

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
O1 H1 O3 1.03(2) 1.48(2) 2.4952(17) 168.0(19) .
N1 H3 O2 0.889(19) 2.07(2) 2.944(2) 167.4(17) .
N2 H5 O2 0.868(17) 2.141(17) 2.9409(18) 152.9(14) 2_655
N2 H6 O3 0.894(17) 2.020(18) 2.9115(19) 174.9(13) 3_565
N1 H4 O2 0.864(19) 2.440(18) 3.142(2) 138.7(15) 2_655
N1 H4 O1 0.864(19) 2.505(19) 3.158(2) 133.0(15) 4_566

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 992788'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_urea_fumaica_300k

_audit_update_record             
;
2011-05-11 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(urea) (E)-butenedioic acid
;
_chemical_name_common            'bis(urea) fumaric acid'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H12 N4 O6'
_chemical_formula_weight         236.20

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.541(6)
_cell_length_b                   8.214(7)
_cell_length_c                   12.427(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.314(8)
_cell_angle_gamma                90.00
_cell_volume                     561.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    4836
_cell_measurement_theta_min      6.14
_cell_measurement_theta_max      55.06

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9130
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7119
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1285
_reflns_number_gt                1024
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0346P)²+0.1395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1285
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.200
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5675(3) 0.20519(19) -0.03736(10) 0.0634(5) Uani 1 1 d . . .
O2 O 0.7486(2) 0.14546(18) 0.12701(10) 0.0634(4) Uani 1 1 d . . .
C1 C 0.7363(3) 0.1359(2) 0.02914(14) 0.0478(5) Uani 1 1 d . . .
C2 C 0.9107(3) 0.0406(3) -0.02547(16) 0.0536(5) Uani 1 1 d . . .
O3 O 0.2523(2) 0.37256(18) 0.03814(10) 0.0631(4) Uani 1 1 d . . .
N1 N 0.4075(4) 0.3745(3) 0.21390(16) 0.0863(8) Uani 1 1 d . . .
N2 N 0.0675(3) 0.5206(3) 0.15472(16) 0.0641(5) Uani 1 1 d . . .
C3 C 0.2432(3) 0.4219(3) 0.13306(14) 0.0535(5) Uani 1 1 d . . .
H1 H 0.452(5) 0.268(3) 0.002(2) 0.093(8) Uiso 1 1 d . . .
H6 H -0.036(4) 0.549(3) 0.1008(19) 0.065(6) Uiso 1 1 d . . .
H2 H 0.887(4) 0.041(3) -0.100(2) 0.076(7) Uiso 1 1 d . . .
H5 H 0.071(4) 0.562(3) 0.2169(19) 0.061(6) Uiso 1 1 d . . .
H4 H 0.395(4) 0.406(3) 0.275(2) 0.083(8) Uiso 1 1 d . . .
H3 H 0.520(4) 0.305(3) 0.1991(19) 0.077(7) Uiso 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(9) 0.0826(10) 0.0386(7) -0.0015(7) 0.0002(6) 0.0305(8)
O2 0.0682(9) 0.0827(11) 0.0388(7) 0.0043(7) 0.0053(6) 0.0228(8)
C1 0.0511(10) 0.0519(11) 0.0395(9) 0.0036(8) 0.0027(8) 0.0030(9)
C2 0.0567(11) 0.0649(13) 0.0390(10) 0.0009(9) 0.0052(8) 0.0087(9)
O3 0.0669(9) 0.0792(10) 0.0401(7) -0.0122(7) -0.0046(6) 0.0262(7)
N1 0.0882(15) 0.124(2) 0.0417(10) -0.0182(11) -0.0106(10) 0.0471(14)
N2 0.0632(11) 0.0829(14) 0.0441(10) -0.0163(10) -0.0007(9) 0.0177(10)
C3 0.0549(11) 0.0634(12) 0.0404(10) -0.0075(9) -0.0009(8) 0.0062(10)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.298(2) . ?
O2 C1 1.212(2) . ?
C1 C2 1.474(3) . ?
C2 C2 1.291(4) 3_755 ?
O3 C3 1.254(2) . ?
N1 C3 1.325(3) . ?
N2 C3 1.321(3) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 123.66(17) . . ?
O2 C1 C2 122.68(17) . . ?
O1 C1 C2 113.66(16) . . ?
C2 C2 C1 123.7(2) 3_755 . ?
O3 C3 N2 120.57(17) . . ?
O3 C3 N1 120.8(2) . . ?
N2 C3 N1 118.58(19) . . ?

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
O1 H1 O3 0.99(3) 1.52(3) 2.498(2) 168(2) .
N1 H3 O2 0.88(3) 2.10(3) 2.966(3) 167(2) .
N2 H5 O2 0.84(2) 2.18(2) 2.957(3) 153.9(19) 2_655
N2 H6 O3 0.86(2) 2.07(2) 2.928(3) 173.3(19) 3_565
N1 H4 O2 0.82(3) 2.49(3) 3.169(3) 141(2) 2_655
N1 H4 O1 0.82(3) 2.57(3) 3.174(3) 132(2) 4_566

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 992789'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_musuc_20

# start Validation Reply Form
_vrf_TYPE031_musuc_20            
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N-methylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(methylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 O6'
_chemical_formula_weight         266.00

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   7.890(5)
_cell_length_b                   5.790(5)
_cell_length_c                   13.650(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.22
_cell_angle_gamma                90.00
_cell_volume                     623.4(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    20
_cell_measurement_reflns_used    250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          2.5
_exptl_crystal_size_mid          1.0
_exptl_crystal_size_min          0.8
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             12
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
For peak integration a local UB matrix was refined for each pattern, 
using approximately 250 reflections.
Hence _cell_measurement_reflns_used      250

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.8-5.2 Angstroms.
;

_diffrn_ambient_temperature      20
_diffrn_radiation_wavelength     0.80-5.20
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ILL reactor source, thermal guide'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  VIVALDI
_diffrn_measurement_method       'Laue patterns at 10 orientations'
_diffrn_detector_area_resol_mean 0.7
_diffrn_standards_number         none
_diffrn_reflns_number            13957
_diffrn_reflns_av_R_equivalents  0.1364
_diffrn_reflns_av_sigmaI/netI    0.0854
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_number_total             2522
_reflns_number_gt                1945
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'VIVALDI (MAATEL)'
_computing_cell_refinement       'lauegen (CCP4)'
_computing_data_reduction        'argonne_boxes, laue4 (Piltz, 2011)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
The variable wavelength nature of the data collection procedure means that
meaningful values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min  0.03  
_diffrn_reflns_sin(theta)/lambda_max  0.93  

_refine_diff_density_max/min is given in Fermi per Angstrom cubed not
electrons per angstrom cubed. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2522
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.344
_refine_ls_restrained_S_all      1.344
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
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)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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
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) .

_refine_diff_density_max         0.121
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.025
_database_code_depnum_ccdc_archive 'CCDC 992790'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_musuc_100

# start Validation Reply Form
_vrf_TYPE031_musuc_100           
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N-methylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(methylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 O6'
_chemical_formula_weight         266.00

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   8.020(5)
_cell_length_b                   5.750(5)
_cell_length_c                   13.740(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.43
_cell_angle_gamma                90.00
_cell_volume                     633.4(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          2.5
_exptl_crystal_size_mid          1.0
_exptl_crystal_size_min          0.8
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             12
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
using approximately 250 reflections.
Hence _cell_measurement_reflns_used      250

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.8-5.2 Angstroms.
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.80-5.20
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ILL reactor source, thermal guide'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  VIVALDI
_diffrn_measurement_method       'Laue patterns at 10 orientations'
_diffrn_detector_area_resol_mean 0.7
_diffrn_standards_number         none
_diffrn_reflns_number            11410
_diffrn_reflns_av_R_equivalents  0.1405
_diffrn_reflns_av_sigmaI/netI    0.0744
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_reflns_number_total             1856
_reflns_number_gt                1410
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'VIVALDI (MAATEL)'
_computing_cell_refinement       'lauegen (CCP4)'
_computing_data_reduction        'argonne_boxes, laue4 (Piltz, 2011)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
The variable wavelength nature of the data collection procedure means that
meaningful values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min  0.03  
_diffrn_reflns_sin(theta)/lambda_max  0.81  

_refine_diff_density_max/min is given in Fermi per Angstrom cubed not
electrons per angstrom cubed. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1856
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.444
_refine_ls_restrained_S_all      1.444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.4420(4) 0.8244(5) 0.4220(2) 0.0385(7) Uani 1 1 d . . .
H6 H 1.0443(3) -0.0811(4) 0.57745(16) 0.0310(6) Uani 1 1 d . . .
H3 H 0.6186(4) 1.0020(4) 0.4129(2) 0.0369(7) Uani 1 1 d . . .
H5 H 0.8971(4) 0.3150(4) 0.75888(16) 0.0330(6) Uani 1 1 d . . .
H4 H 0.8174(4) 0.4970(4) 0.66763(18) 0.0339(7) Uani 1 1 d . . .
H1 H 0.7820(4) 0.4613(4) 0.49229(17) 0.0301(6) Uani 1 1 d . . .
H9 H 1.1372(8) -0.2048(9) 0.7288(3) 0.091(2) Uani 1 1 d . . .
H7 H 0.9639(7) -0.0897(12) 0.7774(3) 0.0801(15) Uani 1 1 d . . .
H8 H 1.1296(8) 0.0751(8) 0.7732(3) 0.0945(19) Uani 1 1 d . . .
O2 O 0.6700(2) 0.73040(19) 0.60480(8) 0.0195(3) Uani 1 1 d . . .
O1 O 0.70662(19) 0.5804(2) 0.45647(8) 0.0209(3) Uani 1 1 d . . .
O3 O 0.8901(2) 0.25895(19) 0.52703(9) 0.0214(3) Uani 1 1 d . . .
C2 C 0.53894(14) 0.91389(16) 0.46512(7) 0.0160(2) Uani 1 1 d . . .
N2 N 1.01792(12) 0.02252(12) 0.63568(5) 0.0189(2) Uani 1 1 d . . .
C3 C 0.93000(15) 0.21383(16) 0.61471(7) 0.0155(2) Uani 1 1 d . . .
C1 C 0.64469(16) 0.73342(15) 0.51640(7) 0.0148(2) Uani 1 1 d . . .
C4 C 1.06844(18) -0.0518(2) 0.73267(8) 0.0224(3) Uani 1 1 d . . .
N1 N 0.88634(12) 0.35751(13) 0.68739(5) 0.0232(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
H2 0.0429(18) 0.0345(11) 0.0372(12) -0.0122(9) -0.0178(12) 0.0101(11)
H6 0.0394(17) 0.0284(10) 0.0253(10) -0.0027(7) 0.0005(10) 0.0133(9)
H3 0.044(2) 0.0375(13) 0.0303(12) 0.0110(8) 0.0155(13) 0.0097(10)
H5 0.0477(18) 0.0323(10) 0.0190(9) 0.0026(7) 0.0035(10) 0.0063(10)
H4 0.048(2) 0.0287(11) 0.0251(10) 0.0001(7) 0.0039(12) 0.0134(10)
H1 0.0368(16) 0.0285(9) 0.0249(10) -0.0011(7) -0.0010(10) 0.0107(10)
H9 0.142(5) 0.088(3) 0.0421(18) 0.0087(18) -0.002(2) 0.087(3)
H7 0.066(3) 0.128(4) 0.048(2) 0.042(3) 0.020(2) 0.014(3)
H8 0.148(5) 0.076(3) 0.056(2) 0.0170(19) -0.062(3) -0.037(3)
O2 0.0291(9) 0.0186(5) 0.0107(5) -0.0003(3) 0.0009(5) 0.0073(4)
O1 0.0279(8) 0.0212(5) 0.0134(5) -0.0029(4) -0.0020(5) 0.0116(5)
O3 0.0300(9) 0.0208(5) 0.0134(5) -0.0006(3) -0.0014(5) 0.0104(4)
C2 0.0205(7) 0.0160(4) 0.0115(4) -0.0004(3) 0.0002(4) 0.0045(4)
N2 0.0244(5) 0.0186(3) 0.0138(3) 0.0009(2) 0.0002(3) 0.0071(3)
C3 0.0188(7) 0.0157(4) 0.0121(4) 0.0003(3) 0.0012(4) 0.0035(3)
C1 0.0186(7) 0.0145(4) 0.0112(4) -0.0006(3) -0.0003(4) 0.0031(3)
C4 0.0285(8) 0.0229(5) 0.0160(4) 0.0045(3) -0.0002(5) 0.0069(4)
N1 0.0353(6) 0.0213(3) 0.0129(3) -0.0003(2) 0.0011(3) 0.0096(3)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2267(15) . ?
O1 C1 1.3112(16) . ?
O3 C3 1.2656(15) . ?
C2 C1 1.5042(15) . ?
C2 C2 1.523(2) 3_676 ?
N2 C3 1.3342(14) . ?
N2 C4 1.4477(13) . ?
C3 N1 1.3490(14) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C2 112.90(10) . 3_676 ?
C3 N2 C4 125.20(9) . . ?
O3 C3 N2 119.61(10) . . ?
O3 C3 N1 121.00(10) . . ?
N2 C3 N1 119.38(9) . . ?
O2 C1 O1 123.80(11) . . ?
O2 C1 C2 123.44(11) . . ?
O1 C1 C2 112.75(9) . . ?

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
O1 H1 O3 1.030(2) 1.521(3) 2.540(2) 169.0(2) .
N1 H4 O2 1.008(2) 1.973(3) 2.966(2) 168.0(2) .

_refine_diff_density_max         0.079
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.017
_database_code_depnum_ccdc_archive 'CCDC 992791'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_musuc_200

# start Validation Reply Form
_vrf_TYPE031_musuc_200           
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N-methylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(methylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 O6'
_chemical_formula_weight         266.00

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   8.290(5)
_cell_length_b                   5.660(5)
_cell_length_c                   13.780(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.80
_cell_angle_gamma                90.00
_cell_volume                     646.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          2.5
_exptl_crystal_size_mid          1.0
_exptl_crystal_size_min          0.8
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             12
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
For peak integration a local UB matrix was refined for each pattern, 
using approximately 250 reflections.
Hence _cell_measurement_reflns_used      250

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.8-5.2 Angstroms.
;

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.80-5.20
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ILL reactor source, thermal guide'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  VIVALDI
_diffrn_measurement_method       'Laue patterns at 10 orientations'
_diffrn_detector_area_resol_mean 0.7
_diffrn_standards_number         none
_diffrn_reflns_number            9049
_diffrn_reflns_av_R_equivalents  0.1681
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_number_total             1400
_reflns_number_gt                994
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'VIVALDI (MAATEL)'
_computing_cell_refinement       'lauegen (CCP4)'
_computing_data_reduction        'argonne_boxes, laue4 (Piltz, 2011)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
The variable wavelength nature of the data collection procedure means that
meaningful values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min  0.03  
_diffrn_reflns_sin(theta)/lambda_max  0.71  

_refine_diff_density_max/min is given in Fermi per Angstrom cubed not
electrons per angstrom cubed. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1400
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.472
_refine_ls_restrained_S_all      1.472
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.4490(5) 0.8239(7) 0.4205(3) 0.0598(11) Uani 1 1 d . . .
H6 H 1.0422(5) -0.0830(6) 0.5761(2) 0.0499(9) Uani 1 1 d . . .
H3 H 0.6161(6) 1.0108(6) 0.4157(3) 0.0605(11) Uani 1 1 d . . .
H5 H 0.8947(5) 0.3074(6) 0.7582(2) 0.0519(9) Uani 1 1 d . . .
H4 H 0.8110(5) 0.4895(6) 0.6678(2) 0.0536(11) Uani 1 1 d . . .
H1 H 0.7827(5) 0.4634(6) 0.4923(2) 0.0493(9) Uani 1 1 d . . .
H9 H 1.1323(11) -0.2102(13) 0.7272(4) 0.130(3) Uani 1 1 d . . .
H7 H 0.9731(10) -0.0905(17) 0.7769(5) 0.121(3) Uani 1 1 d . . .
H8 H 1.1289(12) 0.0727(13) 0.7686(6) 0.147(4) Uani 1 1 d . . .
O2 O 0.6627(3) 0.7225(3) 0.60400(12) 0.0381(5) Uani 1 1 d . . .
O1 O 0.7108(3) 0.5873(3) 0.45622(12) 0.0427(6) Uani 1 1 d . . .
O3 O 0.8836(3) 0.2546(3) 0.52776(14) 0.0417(5) Uani 1 1 d . . .
C2 C 0.5401(2) 0.9162(3) 0.46556(10) 0.0315(4) Uani 1 1 d . . .
N2 N 1.01261(17) 0.01634(19) 0.63495(8) 0.0365(3) Uani 1 1 d . . .
C3 C 0.9238(2) 0.2076(3) 0.61466(10) 0.0309(4) Uani 1 1 d . . .
C1 C 0.6436(2) 0.7334(2) 0.51647(10) 0.0283(4) Uani 1 1 d . . .
C4 C 1.0683(3) -0.0558(3) 0.73062(13) 0.0435(5) Uani 1 1 d . . .
N1 N 0.87944(18) 0.3499(2) 0.68733(8) 0.0438(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
H2 0.065(3) 0.0591(19) 0.0534(19) -0.0191(16) -0.0232(18) 0.0177(19)
H6 0.065(3) 0.0481(17) 0.0365(15) -0.0008(14) 0.0003(15) 0.0210(17)
H3 0.076(3) 0.060(2) 0.047(2) 0.0186(15) 0.022(2) 0.0172(19)
H5 0.074(3) 0.0493(16) 0.0318(15) 0.0019(13) 0.0007(15) 0.0078(18)
H4 0.073(3) 0.0478(18) 0.0400(18) -0.0030(12) 0.005(2) 0.0225(17)
H1 0.065(3) 0.0473(16) 0.0356(16) -0.0025(12) 0.0007(16) 0.0241(17)
H9 0.197(8) 0.126(5) 0.065(3) 0.012(3) -0.010(4) 0.114(5)
H7 0.121(6) 0.176(8) 0.066(3) 0.058(4) 0.027(4) 0.032(5)
H8 0.210(8) 0.124(5) 0.102(4) 0.038(4) -0.106(5) -0.060(6)
O2 0.0554(14) 0.0364(9) 0.0224(7) 0.0004(6) 0.0020(8) 0.0153(8)
O1 0.0602(15) 0.0447(10) 0.0229(7) -0.0041(7) -0.0016(8) 0.0257(10)
O3 0.0586(14) 0.0418(10) 0.0246(8) -0.0017(6) 0.0005(8) 0.0237(8)
C2 0.0423(11) 0.0297(7) 0.0225(6) -0.0001(5) -0.0007(7) 0.0088(6)
N2 0.0478(9) 0.0355(6) 0.0262(5) 0.0017(4) 0.0004(5) 0.0136(5)
C3 0.0389(10) 0.0307(6) 0.0231(6) 0.0009(5) 0.0025(6) 0.0084(6)
C1 0.0364(10) 0.0259(6) 0.0226(6) -0.0008(4) 0.0008(6) 0.0058(5)
C4 0.0555(15) 0.0434(9) 0.0314(8) 0.0076(7) -0.0006(9) 0.0129(9)
N1 0.0669(10) 0.0405(6) 0.0241(5) -0.0016(4) 0.0026(5) 0.0194(6)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.213(2) . ?
O1 C1 1.309(2) . ?
O3 C3 1.261(2) . ?
C2 C1 1.504(2) . ?
C2 C2 1.510(3) 3_676 ?
N2 C3 1.3339(19) . ?
N2 C4 1.4419(19) . ?
C3 N1 1.3452(19) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C2 113.24(14) . 3_676 ?
C3 N2 C4 125.45(13) . . ?
O3 C3 N2 119.86(14) . . ?
O3 C3 N1 120.68(15) . . ?
N2 C3 N1 119.46(12) . . ?
O2 C1 O1 123.59(16) . . ?
O2 C1 C2 123.65(15) . . ?
O1 C1 C2 112.76(13) . . ?

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
O1 H1 O3 1.038(4) 1.519(4) 2.546(3) 169.2(3) .
N1 H4 O2 1.005(4) 1.989(4) 2.977(3) 167.4(3) .

_refine_diff_density_max         0.064
_refine_diff_density_min         -0.082
_refine_diff_density_rms         0.012
_database_code_depnum_ccdc_archive 'CCDC 992792'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_musuc_300

# start Validation Reply Form
_vrf_TYPE031_musuc_300           
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N-methylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(methylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 O6'
_chemical_formula_weight         266.00

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   8.540(5)
_cell_length_b                   5.580(5)
_cell_length_c                   13.840(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.92
_cell_angle_gamma                90.00
_cell_volume                     658.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          2.5
_exptl_crystal_size_mid          1.0
_exptl_crystal_size_min          0.8
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             12
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
For peak integration a local UB matrix was refined for each pattern, 
using approximately 250 reflections.
Hence _cell_measurement_reflns_used      250

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.8-5.2 Angstroms.
;

_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.80-5.20
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ILL reactor source, thermal guide'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  VIVALDI
_diffrn_measurement_method       'Laue patterns at 10 orientations'
_diffrn_detector_area_resol_mean 0.7
_diffrn_standards_number         none
_diffrn_reflns_number            5368
_diffrn_reflns_av_R_equivalents  0.1569
_diffrn_reflns_av_sigmaI/netI    0.0907
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_number_total             893
_reflns_number_gt                636
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'VIVALDI (MAATEL)'
_computing_cell_refinement       'lauegen (CCP4)'
_computing_data_reduction        'argonne_boxes, laue4 (Piltz, 2011)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
The variable wavelength nature of the data collection procedure means that
meaningful values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min  0.03  
_diffrn_reflns_sin(theta)/lambda_max  0.60  

_refine_diff_density_max/min is given in Fermi per Angstrom cubed not
electrons per angstrom cubed. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         893
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.381
_refine_ls_restrained_S_all      1.381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.4563(7) 0.8237(10) 0.4199(4) 0.0866(16) Uani 1 1 d . . .
H6 H 1.0410(7) -0.0841(9) 0.5758(4) 0.0749(15) Uani 1 1 d . . .
H3 H 0.6117(8) 1.0161(9) 0.4177(4) 0.0886(18) Uani 1 1 d . . .
H5 H 0.8913(7) 0.2999(8) 0.7568(4) 0.0760(14) Uani 1 1 d . . .
H4 H 0.8054(7) 0.4826(9) 0.6683(3) 0.0753(15) Uani 1 1 d . . .
H1 H 0.7817(7) 0.4674(8) 0.4923(3) 0.0675(14) Uani 1 1 d . . .
H9 H 1.1285(15) -0.2139(19) 0.7252(6) 0.162(5) Uani 1 1 d . . .
H7 H 0.9857(14) -0.086(2) 0.7757(6) 0.160(5) Uani 1 1 d . . .
H8 H 1.1342(17) 0.066(2) 0.7613(9) 0.199(7) Uani 1 1 d . . .
O2 O 0.6575(4) 0.7167(4) 0.60320(16) 0.0583(8) Uani 1 1 d . . .
O1 O 0.7131(4) 0.5922(5) 0.45690(17) 0.0649(9) Uani 1 1 d . . .
O3 O 0.8786(4) 0.2514(4) 0.52831(18) 0.0637(8) Uani 1 1 d . . .
C2 C 0.5411(3) 0.9177(4) 0.46550(15) 0.0485(7) Uani 1 1 d . . .
N2 N 1.0086(2) 0.0126(3) 0.63435(12) 0.0558(6) Uani 1 1 d . . .
C3 C 0.9192(3) 0.2032(4) 0.61436(13) 0.0470(6) Uani 1 1 d . . .
C1 C 0.6424(3) 0.7335(3) 0.51652(14) 0.0438(6) Uani 1 1 d . . .
C4 C 1.0686(5) -0.0579(6) 0.7283(2) 0.0668(9) Uani 1 1 d . . .
N1 N 0.8738(2) 0.3430(3) 0.68714(13) 0.0656(6) 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 0.100(4) 0.080(3) 0.076(3) -0.020(3) -0.029(3) 0.023(3)
H6 0.101(4) 0.072(3) 0.051(2) -0.002(2) -0.002(3) 0.034(3)
H3 0.114(5) 0.086(3) 0.069(3) 0.032(3) 0.033(3) 0.030(3)
H5 0.106(4) 0.071(2) 0.050(3) 0.001(2) 0.001(3) 0.011(3)
H4 0.104(4) 0.067(3) 0.056(3) -0.005(2) 0.010(3) 0.027(3)
H1 0.088(4) 0.067(3) 0.047(2) -0.0045(18) 0.000(2) 0.031(2)
H9 0.237(11) 0.154(7) 0.091(5) 0.014(4) -0.018(6) 0.131(8)
H7 0.159(10) 0.248(14) 0.075(4) 0.073(7) 0.041(6) 0.067(9)
H8 0.259(14) 0.166(8) 0.156(9) 0.053(7) -0.141(10) -0.084(9)
O2 0.085(2) 0.0567(13) 0.0334(11) 0.0014(9) 0.0052(12) 0.0253(13)
O1 0.089(2) 0.0687(16) 0.0370(12) -0.0040(12) 0.0008(14) 0.0350(16)
O3 0.088(2) 0.0652(16) 0.0378(13) -0.0022(10) 0.0020(13) 0.0380(13)
C2 0.0641(18) 0.0466(11) 0.0345(11) 0.0000(9) 0.0010(13) 0.0170(11)
N2 0.0701(14) 0.0549(9) 0.0424(9) 0.0028(7) 0.0032(9) 0.0206(7)
C3 0.0574(14) 0.0476(10) 0.0362(10) 0.0012(8) 0.0048(9) 0.0128(10)
C1 0.0562(14) 0.0393(9) 0.0356(10) -0.0012(7) -0.0007(10) 0.0098(8)
C4 0.081(3) 0.0695(16) 0.0488(15) 0.0086(13) -0.0033(16) 0.0190(17)
N1 0.0952(15) 0.0617(10) 0.0398(10) -0.0043(8) 0.0032(8) 0.0275(11)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.204(3) . ?
O1 C1 1.311(3) . ?
O3 C3 1.252(3) . ?
C2 C1 1.497(3) . ?
C2 C2 1.522(4) 3_676 ?
N2 C3 1.331(3) . ?
N2 C4 1.428(3) . ?
C3 N1 1.346(3) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C2 113.1(2) . 3_676 ?
C3 N2 C4 125.8(2) . . ?
O3 C3 N2 119.8(2) . . ?
O3 C3 N1 120.7(2) . . ?
N2 C3 N1 119.44(17) . . ?
O2 C1 O1 123.5(2) . . ?
O2 C1 C2 123.6(2) . . ?
O1 C1 C2 112.93(18) . . ?

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
O1 H1 O3 1.019(6) 1.531(5) 2.540(4) 169.2(4) .
N1 H4 O2 1.000(7) 1.999(6) 2.982(3) 166.7(4) .

_refine_diff_density_max         0.042
_refine_diff_density_min         -0.042
_refine_diff_density_rms         0.008
_database_code_depnum_ccdc_archive 'CCDC 992793'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mu_suc_100k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N-methylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(methylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 O6'
_chemical_formula_weight         266.26

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   8.0244(12)
_cell_length_b                   5.7496(7)
_cell_length_c                   13.735(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.246(5)
_cell_angle_gamma                90.00
_cell_volume                     633.54(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6503
_cell_measurement_theta_min      7.09
_cell_measurement_theta_max      55.15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8544
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8408
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.84
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1457
_reflns_number_gt                1304
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.1257P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1457
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
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)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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
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) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 992794'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mu_suc_200k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N-methylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(methylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 O6'
_chemical_formula_weight         266.26

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   8.2868(7)
_cell_length_b                   5.6618(3)
_cell_length_c                   13.7761(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.799(4)
_cell_angle_gamma                90.00
_cell_volume                     646.03(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    6425
_cell_measurement_theta_min      7.20
_cell_measurement_theta_max      55.14

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9161
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8559
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.89
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1480
_reflns_number_gt                1147
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.0515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1480
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.4615(19) 0.832(3) 0.4240(13) 0.053(4) Uiso 1 1 d . . .
H6 H 1.040(2) -0.070(3) 0.5866(14) 0.057(5) Uiso 1 1 d . . .
H3 H 0.6027(19) 0.998(3) 0.4248(12) 0.053(4) Uiso 1 1 d . . .
H5 H 0.8961(19) 0.318(3) 0.7484(13) 0.052(4) Uiso 1 1 d . . .
H4 H 0.819(2) 0.476(3) 0.6691(13) 0.058(4) Uiso 1 1 d . . .
H1 H 0.774(3) 0.479(4) 0.4904(18) 0.093(6) Uiso 1 1 d . . .
H9 H 1.136(3) -0.190(5) 0.7253(16) 0.093(7) Uiso 1 1 d . . .
H7 H 0.980(3) -0.104(4) 0.7707(19) 0.105(8) Uiso 1 1 d . . .
H8 H 1.119(3) 0.068(5) 0.7675(19) 0.108(8) Uiso 1 1 d . . .
O2 O 0.66220(12) 0.72162(16) 0.60424(6) 0.0459(3) Uani 1 1 d . . .
O1 O 0.71081(13) 0.58787(18) 0.45622(6) 0.0507(3) Uani 1 1 d . . .
O3 O 0.88240(12) 0.25330(17) 0.52788(6) 0.0492(3) Uani 1 1 d . . .
C2 C 0.53957(17) 0.9161(2) 0.46549(9) 0.0387(3) Uani 1 1 d . . .
N2 N 1.01197(14) 0.0160(2) 0.63501(8) 0.0438(3) Uani 1 1 d . . .
C3 C 0.92342(15) 0.2072(2) 0.61476(9) 0.0389(3) Uani 1 1 d . . .
C1 C 0.64322(14) 0.7336(2) 0.51651(8) 0.0353(3) Uani 1 1 d . . .
C4 C 1.0685(2) -0.0555(3) 0.73048(11) 0.0518(4) Uani 1 1 d . . .
N1 N 0.87875(17) 0.3486(2) 0.68707(9) 0.0513(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
O2 0.0619(6) 0.0465(5) 0.0294(5) 0.0013(4) 0.0010(4) 0.0153(4)
O1 0.0658(6) 0.0546(6) 0.0314(5) -0.0042(4) -0.0031(4) 0.0267(5)
O3 0.0660(6) 0.0515(6) 0.0301(5) -0.0006(4) -0.0006(4) 0.0236(5)
C2 0.0486(7) 0.0383(7) 0.0290(6) 0.0001(5) -0.0002(5) 0.0083(5)
N2 0.0538(7) 0.0458(6) 0.0319(6) 0.0014(5) 0.0007(5) 0.0134(5)
C3 0.0447(6) 0.0406(6) 0.0313(6) 0.0011(5) 0.0018(5) 0.0056(5)
C1 0.0407(6) 0.0355(6) 0.0297(6) -0.0005(4) 0.0004(4) 0.0016(5)
C4 0.0624(9) 0.0555(9) 0.0373(7) 0.0066(6) -0.0020(6) 0.0145(8)
N1 0.0742(8) 0.0496(7) 0.0299(6) 0.0002(5) 0.0004(5) 0.0217(6)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2158(14) . ?
O1 C1 1.3091(14) . ?
O3 C3 1.2612(15) . ?
C2 C1 1.5038(16) . ?
C2 C2 1.509(2) 3_676 ?
N2 C3 1.3322(17) . ?
N2 C4 1.4403(17) . ?
C3 N1 1.3393(17) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C2 113.03(12) . 3_676 ?
C3 N2 C4 125.52(12) . . ?
O3 C3 N2 119.81(11) . . ?
O3 C3 N1 120.63(12) . . ?
N2 C3 N1 119.56(12) . . ?
O2 C1 O1 123.42(11) . . ?
O2 C1 C2 123.87(10) . . ?
O1 C1 C2 112.71(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
_geom_hbond_site_symmetry_A
O1 H1 O3 0.93(3) 1.64(3) 2.5488(12) 167(2) .
N1 H4 O2 0.90(2) 2.09(2) 2.9755(16) 167.7(16) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 992795'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mu_suc_300k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N-methylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(methylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 O6'
_chemical_formula_weight         266.26

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   8.5398(8)
_cell_length_b                   5.5798(4)
_cell_length_c                   13.8377(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.291(4)
_cell_angle_gamma                90.00
_cell_volume                     658.84(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    4642
_cell_measurement_theta_min      7.30
_cell_measurement_theta_max      55.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8229
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8658
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.94
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1501
_reflns_number_gt                851
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.1040P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1501
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.469(3) 0.827(4) 0.4212(19) 0.075(7) Uiso 1 1 d . . .
H6 H 1.041(3) -0.071(5) 0.585(2) 0.083(8) Uiso 1 1 d . . .
H3 H 0.603(3) 1.005(5) 0.4269(19) 0.085(8) Uiso 1 1 d . . .
H5 H 0.896(3) 0.308(5) 0.747(2) 0.082(8) Uiso 1 1 d . . .
H4 H 0.810(4) 0.471(6) 0.667(2) 0.105(9) Uiso 1 1 d . . .
H1 H 0.774(4) 0.474(7) 0.494(3) 0.134(12) Uiso 1 1 d . . .
H9 H 1.133(4) -0.199(7) 0.720(2) 0.128(12) Uiso 1 1 d . . .
H7 H 0.983(5) -0.124(7) 0.771(3) 0.157(15) Uiso 1 1 d . . .
H8 H 1.117(5) 0.066(9) 0.761(3) 0.170(18) Uiso 1 1 d . . .
O2 O 0.65696(19) 0.7154(3) 0.60340(9) 0.0686(5) Uani 1 1 d . . .
O1 O 0.7131(2) 0.5932(3) 0.45673(10) 0.0755(5) Uani 1 1 d . . .
O3 O 0.87795(19) 0.2502(3) 0.52845(10) 0.0741(5) Uani 1 1 d . . .
C2 C 0.5405(3) 0.9181(4) 0.46588(15) 0.0580(5) Uani 1 1 d . . .
N2 N 1.0085(2) 0.0127(3) 0.63413(13) 0.0649(5) Uani 1 1 d . . .
C3 C 0.9190(2) 0.2025(4) 0.61458(14) 0.0578(5) Uani 1 1 d . . .
C1 C 0.6420(2) 0.7344(3) 0.51648(13) 0.0534(5) Uani 1 1 d . . .
C4 C 1.0686(4) -0.0577(6) 0.72875(19) 0.0795(8) Uani 1 1 d . . .
N1 N 0.8733(3) 0.3416(4) 0.68666(15) 0.0771(6) 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 0.0926(11) 0.0715(10) 0.0417(8) 0.0030(6) 0.0035(7) 0.0230(8)
O1 0.1013(13) 0.0796(11) 0.0452(8) -0.0039(7) -0.0017(7) 0.0379(9)
O3 0.1019(12) 0.0776(11) 0.0426(8) -0.0004(7) 0.0002(7) 0.0366(9)
C2 0.0729(14) 0.0563(12) 0.0444(11) -0.0004(9) -0.0011(10) 0.0117(10)
N2 0.0801(12) 0.0685(11) 0.0459(10) 0.0018(8) 0.0003(8) 0.0226(10)
C3 0.0678(12) 0.0612(12) 0.0445(10) 0.0007(9) 0.0043(9) 0.0094(10)
C1 0.0660(12) 0.0529(11) 0.0412(10) -0.0010(8) 0.0018(8) 0.0042(9)
C4 0.100(2) 0.0850(18) 0.0532(13) 0.0099(13) -0.0044(13) 0.0230(17)
N1 0.1093(17) 0.0775(13) 0.0445(10) -0.0018(10) 0.0008(10) 0.0303(12)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.209(2) . ?
O1 C1 1.309(2) . ?
O3 C3 1.257(2) . ?
C2 C1 1.498(3) . ?
C2 C2 1.503(4) 3_676 ?
N2 C3 1.327(3) . ?
N2 C4 1.442(3) . ?
C3 N1 1.335(3) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C2 113.3(2) . 3_676 ?
C3 N2 C4 125.7(2) . . ?
O3 C3 N2 119.90(18) . . ?
O3 C3 N1 120.4(2) . . ?
N2 C3 N1 119.7(2) . . ?
O2 C1 O1 122.84(18) . . ?
O2 C1 C2 124.14(17) . . ?
O1 C1 C2 113.02(16) . . ?

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
O1 H1 O3 0.98(4) 1.59(4) 2.553(2) 166(3) .
N1 H4 O2 0.94(3) 2.06(4) 2.987(3) 170(3) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 992796'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mu_fum_100k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N-methylurea) trans-butenedioic acid
;
_chemical_name_common            
;
 bis(methylurea) fumaric acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H16 N4 O6'
_chemical_formula_weight         264.25

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   8.3188(10)
_cell_length_b                   5.6497(5)
_cell_length_c                   13.8382(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.156(4)
_cell_angle_gamma                90.00
_cell_volume                     630.63(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5410
_cell_measurement_theta_min      6.07
_cell_measurement_theta_max      55.14

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8385
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8243
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1449
_reflns_number_gt                1172
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0379P)²+0.1082P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1449
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H8 H 0.968(2) -0.185(3) 0.7567(11) 0.044(4) Uiso 1 1 d . . .
H3 H 0.8958(17) 0.228(3) 0.7496(12) 0.031(4) Uiso 1 1 d . . .
H1 H 0.9289(16) 0.494(2) 1.0835(10) 0.028(3) Uiso 1 1 d . . .
H5 H 1.0474(18) -0.087(3) 0.5860(11) 0.034(4) Uiso 1 1 d . . .
H6 H 1.133(2) -0.271(3) 0.7291(12) 0.060(5) Uiso 1 1 d . . .
H2 H 0.706(2) -0.012(3) 0.9995(15) 0.073(6) Uiso 1 1 d . . .
H4 H 0.8060(19) 0.407(3) 0.6708(11) 0.038(4) Uiso 1 1 d . . .
H7 H 1.129(2) -0.020(3) 0.7828(12) 0.048(4) Uiso 1 1 d . . .
O1 O 0.86193(11) 0.15464(15) 0.89383(6) 0.0298(2) Uani 1 1 d . . .
O2 O 0.76618(10) 0.13618(16) 1.03156(6) 0.0266(2) Uani 1 1 d . . .
O3 O 0.88388(10) 0.25347(15) 0.52710(6) 0.0269(2) Uani 1 1 d . . .
N1 N 1.01622(13) -0.02227(19) 0.63523(7) 0.0271(3) Uani 1 1 d . . .
C3 C 0.92465(14) 0.1738(2) 0.61528(8) 0.0234(3) Uani 1 1 d . . .
C2 C 0.94804(15) 0.4440(2) 1.02128(9) 0.0243(3) Uani 1 1 d . . .
N2 N 0.87665(15) 0.2838(2) 0.68926(8) 0.0296(3) Uani 1 1 d . . .
C4 C 1.06534(19) -0.1306(3) 0.73298(10) 0.0325(3) Uani 1 1 d . . .
C1 C 0.85476(14) 0.2310(2) 0.97560(8) 0.0233(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 0.0366(5) 0.0338(5) 0.0217(4) -0.0023(4) 0.0124(4) -0.0066(4)
O2 0.0287(5) 0.0319(5) 0.0206(4) -0.0003(4) 0.0089(3) -0.0065(4)
O3 0.0308(5) 0.0321(5) 0.0192(4) 0.0013(3) 0.0088(3) 0.0061(4)
N1 0.0338(6) 0.0303(6) 0.0195(5) 0.0016(4) 0.0108(4) 0.0063(5)
C3 0.0239(6) 0.0264(6) 0.0211(6) -0.0010(5) 0.0080(4) -0.0029(5)
C2 0.0260(6) 0.0277(6) 0.0195(5) 0.0010(5) 0.0060(4) 0.0025(5)
N2 0.0415(7) 0.0299(6) 0.0194(5) 0.0020(5) 0.0114(5) 0.0073(5)
C4 0.0400(8) 0.0344(7) 0.0249(6) 0.0063(6) 0.0112(6) 0.0061(6)
C1 0.0229(6) 0.0275(6) 0.0199(5) 0.0044(5) 0.0059(4) 0.0021(5)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2259(13) . ?
O2 C1 1.3071(13) . ?
O3 C3 1.2666(13) . ?
N1 C3 1.3346(16) . ?
N1 C4 1.4494(16) . ?
C3 N2 1.3392(15) . ?
C2 C2 1.321(2) 3_767 ?
C2 C1 1.4866(17) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C4 124.05(11) . . ?
O3 C3 N1 119.93(10) . . ?
O3 C3 N2 120.81(11) . . ?
N1 C3 N2 119.26(11) . . ?
C2 C2 C1 121.93(14) 3_767 . ?
O1 C1 O2 124.37(11) . . ?
O1 C1 C2 122.62(10) . . ?
O2 C1 C2 113.01(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
_geom_hbond_site_symmetry_A
O2 H2 O3 1.02(2) 1.53(2) 2.5291(12) 168.4(18) 2_646
N2 H4 O1 0.905(17) 2.026(17) 2.9214(15) 170.2(13) 2_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 992797'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mu_fum_200k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N-methylurea) trans-butenedioic acid
;
_chemical_name_common            
;
 bis(methylurea) fumaric acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H16 N4 O6'
_chemical_formula_weight         264.25

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   8.5509(16)
_cell_length_b                   5.5691(8)
_cell_length_c                   13.909(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.959(7)
_cell_angle_gamma                90.00
_cell_volume                     645.47(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    4754
_cell_measurement_theta_min      6.01
_cell_measurement_theta_max      55.06

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8138
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8540
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1475
_reflns_number_gt                1002
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.0178P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1475
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
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)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 992798'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mu_fum_300k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N-methylurea) trans-butenedioic acid
;
_chemical_name_common            
;
 bis(methylurea) fumaric acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H16 N4 O6'
_chemical_formula_weight         264.25

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   8.7741(14)
_cell_length_b                   5.4413(7)
_cell_length_c                   13.9303(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.730(6)
_cell_angle_gamma                90.00
_cell_volume                     653.44(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    3951
_cell_measurement_theta_min      6.04
_cell_measurement_theta_max      54.95

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8368
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8681
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1494
_reflns_number_gt                865
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0437P)²+0.1277P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.004(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1494
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H8 H 0.980(5) -0.196(7) 0.754(3) 0.158(14) Uiso 1 1 d . . .
H3 H 0.888(2) 0.235(4) 0.7447(16) 0.068(6) Uiso 1 1 d . . .
H1 H 0.943(2) 0.490(4) 1.0844(16) 0.074(6) Uiso 1 1 d . . .
H5 H 1.047(3) -0.080(4) 0.5879(18) 0.084(8) Uiso 1 1 d . . .
H6 H 1.137(4) -0.249(6) 0.726(2) 0.133(12) Uiso 1 1 d . . .
H2 H 0.716(3) -0.028(5) 0.997(2) 0.122(9) Uiso 1 1 d . . .
H4 H 0.793(3) 0.415(5) 0.6688(17) 0.095(8) Uiso 1 1 d . . .
H7 H 1.117(4) 0.002(6) 0.776(2) 0.143(13) Uiso 1 1 d . . .
O1 O 0.85879(19) 0.1626(3) 0.89361(10) 0.0799(5) Uani 1 1 d . . .
O2 O 0.77412(17) 0.1295(3) 1.03314(10) 0.0732(5) Uani 1 1 d . . .
O3 O 0.88005(17) 0.2487(3) 0.52868(9) 0.0733(5) Uani 1 1 d . . .
N1 N 1.0150(2) -0.0155(4) 0.63506(13) 0.0733(6) Uani 1 1 d . . .
C3 C 0.9200(2) 0.1746(4) 0.61513(13) 0.0599(5) Uani 1 1 d . . .
C2 C 0.9506(2) 0.4414(4) 1.02133(14) 0.0626(6) Uani 1 1 d . . .
N2 N 0.8665(3) 0.2848(4) 0.68729(15) 0.0804(7) Uani 1 1 d . . .
C4 C 1.0672(4) -0.1201(6) 0.7303(2) 0.0887(8) Uani 1 1 d . . .
C1 C 0.8575(2) 0.2318(4) 0.97613(13) 0.0589(5) 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 0.1044(12) 0.0890(11) 0.0524(8) -0.0089(7) 0.0304(8) -0.0302(9)
O2 0.0889(11) 0.0844(10) 0.0508(8) -0.0029(7) 0.0246(7) -0.0264(9)
O3 0.0905(11) 0.0866(11) 0.0465(8) 0.0050(7) 0.0220(7) 0.0312(9)
N1 0.0891(14) 0.0832(13) 0.0523(10) 0.0071(9) 0.0253(10) 0.0250(11)
C3 0.0668(13) 0.0673(13) 0.0492(11) -0.0003(9) 0.0198(9) 0.0034(11)
C2 0.0768(15) 0.0660(13) 0.0462(11) 0.0013(10) 0.0147(9) -0.0064(10)
N2 0.1132(17) 0.0859(14) 0.0475(10) 0.0038(10) 0.0291(11) 0.0286(12)
C4 0.111(2) 0.0922(19) 0.0635(15) 0.0170(14) 0.0176(15) 0.022(2)
C1 0.0659(13) 0.0655(12) 0.0475(11) 0.0067(9) 0.0158(9) -0.0040(10)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.212(2) . ?
O2 C1 1.301(2) . ?
O3 C3 1.256(2) . ?
N1 C3 1.325(3) . ?
N1 C4 1.438(3) . ?
C3 N2 1.329(3) . ?
C2 C2 1.305(4) 3_767 ?
C2 C1 1.474(3) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C4 125.6(2) . . ?
O3 C3 N1 120.24(18) . . ?
O3 C3 N2 120.4(2) . . ?
N1 C3 N2 119.4(2) . . ?
C2 C2 C1 123.1(2) 3_767 . ?
O1 C1 O2 123.51(19) . . ?
O1 C1 C2 122.91(17) . . ?
O2 C1 C2 113.59(17) . . ?

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 1.07(3) 1.48(3) 2.5359(19) 166(3) 2_646
N2 H4 O1 0.96(3) 1.98(3) 2.928(3) 170(2) 2_656

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 992799'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mu_oxalic_200k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 N-methylurea ethandioic acid
;
_chemical_name_common            
;
 N-methylurea oxalic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H14 N4 O6'
_chemical_formula_weight         238.21

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.1081(8)
_cell_length_b                   10.5388(14)
_cell_length_c                   10.2233(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.717(7)
_cell_angle_gamma                90.00
_cell_volume                     536.85(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    3964
_cell_measurement_theta_min      7.73
_cell_measurement_theta_max      55.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8397
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7002
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.87
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1233
_reflns_number_gt                816
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0572P)²+0.1090P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1233
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.660(5) 0.763(2) 0.652(2) 0.055(7) Uiso 1 1 d . . .
H4 H 0.276(4) 0.734(2) 0.871(2) 0.043(6) Uiso 1 1 d . . .
H1 H 0.653(5) 0.985(3) 0.652(3) 0.076(8) Uiso 1 1 d . . .
H3 H 0.567(5) 0.668(3) 0.737(2) 0.051(7) Uiso 1 1 d . . .
H5 H 0.079(6) 0.970(3) 0.859(3) 0.080(9) Uiso 1 1 d . . .
H6 H 0.282(7) 0.954(3) 0.987(3) 0.100(11) Uiso 1 1 d . . .
H7 H 0.044(7) 0.871(3) 0.966(3) 0.097(11) Uiso 1 1 d . . .
O1 O 0.7817(3) 1.03701(12) 0.60376(14) 0.0397(4) Uani 1 1 d . . .
O3 O 0.4585(3) 0.95196(12) 0.72732(14) 0.0381(4) Uani 1 1 d . . .
O2 O 0.8796(3) 0.84920(12) 0.52475(14) 0.0427(4) Uani 1 1 d . . .
C1 C 0.9047(4) 0.96293(18) 0.53489(18) 0.0330(5) Uani 1 1 d . . .
N2 N 0.5574(4) 0.74394(18) 0.71119(19) 0.0428(5) Uani 1 1 d . . .
C2 C 0.4385(4) 0.83778(18) 0.76341(19) 0.0341(5) Uani 1 1 d . . .
N1 N 0.2944(4) 0.81129(18) 0.85350(17) 0.0404(5) Uani 1 1 d . . .
C3 C 0.1608(5) 0.9077(2) 0.9158(2) 0.0423(5) 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 0.0458(8) 0.0304(8) 0.0489(8) -0.0013(6) 0.0232(7) 0.0000(6)
O3 0.0433(8) 0.0285(8) 0.0466(8) 0.0026(6) 0.0189(6) 0.0002(5)
O2 0.0528(9) 0.0283(8) 0.0527(9) -0.0020(6) 0.0240(7) -0.0026(6)
C1 0.0350(10) 0.0318(11) 0.0320(9) 0.0004(8) 0.0070(8) 0.0018(7)
N2 0.0570(12) 0.0291(10) 0.0479(11) 0.0028(8) 0.0234(9) 0.0039(8)
C2 0.0367(10) 0.0303(10) 0.0348(10) 0.0027(8) 0.0069(8) -0.0004(8)
N1 0.0520(11) 0.0296(10) 0.0450(10) 0.0057(8) 0.0227(8) -0.0002(7)
C3 0.0461(12) 0.0394(12) 0.0459(12) 0.0026(11) 0.0196(10) 0.0027(9)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.302(2) . ?
O3 C2 1.269(2) . ?
O2 C1 1.208(2) . ?
C1 C1 1.540(4) 3_776 ?
N2 C2 1.332(3) . ?
C2 N1 1.329(3) . ?
N1 C3 1.447(3) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 125.94(17) . . ?
O2 C1 C1 122.0(2) . 3_776 ?
O1 C1 C1 112.07(19) . 3_776 ?
O3 C2 N1 119.51(17) . . ?
O3 C2 N2 120.97(18) . . ?
N1 C2 N2 119.51(18) . . ?
C2 N1 C3 122.97(18) . . ?

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
O1 H1 O3 1.06(3) 1.43(3) 2.4583(18) 163(3) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 992800'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mu_oxalic_300k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 N-methylurea ethandioic acid
;
_chemical_name_common            
;
 N-methylurea oxalic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H14 N4 O6'
_chemical_formula_weight         238.21

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.1464(14)
_cell_length_b                   10.555(2)
_cell_length_c                   10.313(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.835(13)
_cell_angle_gamma                90.00
_cell_volume                     548.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    5616
_cell_measurement_theta_min      7.72
_cell_measurement_theta_max      55.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8131
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13815
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.86
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1255
_reflns_number_gt                880
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.1612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1255
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.669(5) 0.766(3) 0.652(3) 0.082(8) Uiso 1 1 d . . .
H4 H 0.279(5) 0.736(3) 0.871(2) 0.068(7) Uiso 1 1 d . . .
H1 H 0.659(5) 0.986(3) 0.651(3) 0.090(8) Uiso 1 1 d . . .
H3 H 0.564(5) 0.671(3) 0.740(2) 0.071(8) Uiso 1 1 d . . .
H5 H 0.094(7) 0.972(3) 0.861(3) 0.120(12) Uiso 1 1 d . . .
H6 H 0.278(8) 0.953(4) 0.979(4) 0.131(13) Uiso 1 1 d . . .
H7 H 0.047(7) 0.870(3) 0.966(3) 0.129(12) Uiso 1 1 d . . .
O1 O 0.7835(3) 1.03631(12) 0.60385(15) 0.0584(5) Uani 1 1 d . . .
O3 O 0.4623(3) 0.95068(12) 0.72794(14) 0.0561(4) Uani 1 1 d . . .
O2 O 0.8809(3) 0.84992(13) 0.52484(15) 0.0636(5) Uani 1 1 d . . .
C1 C 0.9063(4) 0.96328(18) 0.53489(19) 0.0470(5) Uani 1 1 d . . .
N2 N 0.5593(4) 0.7438(2) 0.7122(2) 0.0636(6) Uani 1 1 d . . .
C2 C 0.4412(4) 0.83763(18) 0.7643(2) 0.0488(5) Uani 1 1 d . . .
N1 N 0.2974(4) 0.81155(19) 0.85370(18) 0.0603(5) Uani 1 1 d . . .
C3 C 0.1632(6) 0.9073(3) 0.9151(3) 0.0638(6) 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 0.0686(10) 0.0417(8) 0.0741(10) -0.0009(7) 0.0359(8) 0.0002(7)
O3 0.0658(9) 0.0393(8) 0.0707(10) 0.0065(6) 0.0314(8) 0.0011(6)
O2 0.0789(11) 0.0396(9) 0.0809(11) -0.0039(7) 0.0364(9) -0.0037(7)
C1 0.0507(12) 0.0402(12) 0.0498(11) -0.0002(8) 0.0092(9) 0.0026(8)
N2 0.0851(14) 0.0405(11) 0.0727(13) 0.0062(9) 0.0336(11) 0.0059(9)
C2 0.0521(12) 0.0421(11) 0.0520(11) 0.0037(9) 0.0102(9) -0.0008(8)
N1 0.0759(13) 0.0441(11) 0.0681(12) 0.0100(9) 0.0317(10) 0.0003(9)
C3 0.0686(16) 0.0589(15) 0.0704(16) 0.0019(13) 0.0295(14) 0.0007(12)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.298(2) . ?
O3 C2 1.262(2) . ?
O2 C1 1.206(2) . ?
C1 C1 1.528(4) 3_776 ?
N2 C2 1.332(3) . ?
C2 N1 1.324(3) . ?
N1 C3 1.442(3) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 125.48(18) . . ?
O2 C1 C1 122.1(2) . 3_776 ?
O1 C1 C1 112.5(2) . 3_776 ?
O3 C2 N1 119.85(18) . . ?
O3 C2 N2 120.64(19) . . ?
N1 C2 N2 119.51(19) . . ?
C2 N1 C3 123.2(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
O1 H1 O3 1.03(3) 1.46(3) 2.461(2) 163(2) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 992801'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dmusuc_20

# start Validation Reply Form
_vrf_TYPE031_dmusuc_20           
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N,N-dimethylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(N,N-dimethylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H22 N4 O6'
_chemical_formula_weight         294.00

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   8.350(5)
_cell_length_b                   5.440(5)
_cell_length_c                   15.430(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.950(10)
_cell_angle_gamma                90.00
_cell_volume                     685.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    20
_cell_measurement_reflns_used    250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          2.8
_exptl_crystal_size_mid          1.0
_exptl_crystal_size_min          0.8
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             11
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
For peak integration a local UB matrix was refined for each pattern, 
using approximately 250 reflections.
Hence _cell_measurement_reflns_used      250

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.8-5.2 Angstroms.
;

_diffrn_ambient_temperature      20
_diffrn_radiation_wavelength     0.80-5.20
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ILL reactor source, thermal guide'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  VIVALDI
_diffrn_measurement_method       'Laue patterns at 10 orientations'
_diffrn_detector_area_resol_mean 0.7
_diffrn_standards_number         none
_diffrn_reflns_number            15220
_diffrn_reflns_av_R_equivalents  0.1259
_diffrn_reflns_av_sigmaI/netI    0.0918
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_reflns_number_total             3055
_reflns_number_gt                2334
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'VIVALDI (MAATEL)'
_computing_cell_refinement       'lauegen (CCP4)'
_computing_data_reduction        'argonne_boxes, laue4 (Piltz, 2011)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
The variable wavelength nature of the data collection procedure means that
meaningful values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min  0.03  
_diffrn_reflns_sin(theta)/lambda_max  0.93 

_refine_diff_density_max/min is given in Fermi per Angstrom cubed not
electrons per angstrom cubed. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3055
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.281
_refine_ls_restrained_S_all      1.281
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.3912(2) 0.7531(3) 0.77398(11) 0.0216(4) Uani 1 1 d . . .
H10 H 0.3236(2) -0.0156(3) 0.44737(14) 0.0230(4) Uani 1 1 d . . .
H11 H 0.4736(2) 0.1755(4) 0.42093(11) 0.0226(3) Uani 1 1 d . . .
H5 H 0.2635(3) 0.9827(4) 0.82595(13) 0.0269(4) Uani 1 1 d . . .
H6 H -0.0827(2) 1.1728(5) 0.66356(14) 0.0292(4) Uani 1 1 d . . .
H1 H 0.3930(2) 0.5694(4) 0.68332(11) 0.0207(3) Uani 1 1 d . . .
H7 H -0.0131(3) 1.0661(5) 0.57044(12) 0.0322(5) Uani 1 1 d . . .
H8 H 0.0656(3) 1.3391(4) 0.62348(17) 0.0339(5) Uani 1 1 d . . .
H3 H 0.1062(2) 1.1945(5) 0.80223(14) 0.0319(5) Uani 1 1 d . . .
H4 H 0.2962(3) 1.2616(4) 0.77571(15) 0.0337(5) Uani 1 1 d . . .
H9 H 0.24483(19) 0.5632(3) 0.53327(11) 0.0174(3) Uani 1 1 d . . .
O1 O 0.17890(10) 0.77062(15) 0.57848(5) 0.00687(14) Uani 1 1 d . . .
O3 O 0.44536(9) 0.29492(16) 0.61364(5) 0.00760(14) Uani 1 1 d . . .
O2 O 0.27920(9) 0.43246(17) 0.49231(5) 0.00780(14) Uani 1 1 d . . .
C5 C 0.43454(8) 0.08525(13) 0.47597(4) 0.00582(11) Uani 1 1 d . . .
C1 C 0.22466(7) 0.83298(13) 0.65742(4) 0.00483(11) Uani 1 1 d . . .
N2 N 0.14752(6) 1.01471(9) 0.69130(3) 0.00616(9) Uani 1 1 d . . .
N1 N 0.35035(6) 0.71753(10) 0.70999(3) 0.00762(10) Uani 1 1 d . . .
C3 C 0.20760(8) 1.11804(14) 0.77807(4) 0.00735(12) Uani 1 1 d . . .
C4 C 0.38771(8) 0.27996(13) 0.53466(4) 0.00502(11) Uani 1 1 d . . .
C2 C 0.02274(8) 1.15582(14) 0.63339(5) 0.00837(12) 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 0.0251(8) 0.0247(9) 0.0121(6) -0.0041(5) -0.0026(6) 0.0056(5)
H10 0.0148(6) 0.0213(9) 0.0293(8) -0.0077(6) -0.0036(6) -0.0020(5)
H11 0.0312(8) 0.0243(9) 0.0157(6) 0.0071(6) 0.0126(6) 0.0069(6)
H5 0.0399(10) 0.0228(10) 0.0150(7) 0.0026(6) -0.0009(7) 0.0086(7)
H6 0.0168(7) 0.0426(12) 0.0307(9) 0.0051(8) 0.0107(6) 0.0121(7)
H1 0.0240(7) 0.0172(8) 0.0203(7) -0.0030(6) 0.0035(6) 0.0082(6)
H7 0.0362(10) 0.0374(12) 0.0176(7) -0.0090(7) -0.0068(7) 0.0161(8)
H8 0.0297(9) 0.0191(10) 0.0493(12) 0.0142(9) -0.0001(8) -0.0017(7)
H3 0.0221(8) 0.0482(13) 0.0254(8) -0.0155(9) 0.0053(7) 0.0109(8)
H4 0.0401(11) 0.0348(12) 0.0262(9) -0.0054(8) 0.0071(8) -0.0235(8)
H9 0.0185(6) 0.0180(8) 0.0160(6) -0.0019(5) 0.0040(5) 0.0037(5)
O1 0.0074(3) 0.0082(4) 0.0047(3) -0.0018(2) 0.0005(2) 0.0027(2)
O3 0.0089(3) 0.0085(4) 0.0048(3) -0.0011(2) -0.0001(2) 0.0025(2)
O2 0.0090(3) 0.0089(4) 0.0051(3) -0.0005(2) 0.0005(2) 0.0043(2)
C5 0.0060(2) 0.0067(3) 0.0047(2) -0.0008(2) 0.00100(18) 0.00176(19)
C1 0.0044(2) 0.0059(3) 0.0042(2) -0.00060(19) 0.00094(18) 0.00057(17)
N2 0.00598(18) 0.0073(2) 0.00502(18) -0.00125(13) 0.00073(14) 0.00145(13)
N1 0.00747(19) 0.0087(2) 0.00591(18) -0.00079(15) -0.00044(14) 0.00268(14)
C3 0.0087(2) 0.0070(3) 0.0061(2) -0.0016(2) 0.0010(2) 0.00034(19)
C4 0.0049(2) 0.0054(3) 0.0047(2) -0.00036(19) 0.00095(18) 0.00069(18)
C2 0.0072(2) 0.0097(3) 0.0081(2) -0.0004(2) 0.0011(2) 0.0027(2)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2459(10) . ?
O3 C4 1.2167(10) . ?
O2 C4 1.3004(11) . ?
C5 C4 1.4973(12) . ?
C5 C5 1.5065(14) 3_656 ?
C1 N1 1.3420(9) . ?
C1 N2 1.3435(11) . ?
N2 C3 1.4430(9) . ?
N2 C2 1.4449(10) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 C5 113.05(7) . 3_656 ?
O1 C1 N1 120.44(7) . . ?
O1 C1 N2 120.40(6) . . ?
N1 C1 N2 119.15(6) . . ?
C1 N2 C3 123.03(5) . . ?
C1 N2 C2 119.52(6) . . ?
C3 N2 C2 115.75(6) . . ?
O3 C4 O2 123.41(8) . . ?
O3 C4 C5 123.67(7) . . ?
O2 C4 C5 112.92(7) . . ?

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 H9 O1 1.031(2) 1.491(2) 2.5128(18) 170.33(16) .
N1 H1 O3 1.0032(19) 1.942(2) 2.935(2) 169.90(14) .

_refine_diff_density_max         0.126
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.028
_database_code_depnum_ccdc_archive 'CCDC 992802'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dmusuc_50

# start Validation Reply Form
_vrf_TYPE031_dmusuc_50           
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N,N-dimethylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(N,N-dimethylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H22 N4 O6'
_chemical_formula_weight         294.00

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   8.400(5)
_cell_length_b                   5.470(5)
_cell_length_c                   15.470(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.950(10)
_cell_angle_gamma                90.00
_cell_volume                     695.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    50
_cell_measurement_reflns_used    250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          2.8
_exptl_crystal_size_mid          1.0
_exptl_crystal_size_min          0.8
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             11
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      50
_diffrn_radiation_wavelength     0.80-5.20
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ILL reactor source, thermal guide'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  VIVALDI
_diffrn_measurement_method       'Laue patterns at 10 orientations'
_diffrn_detector_area_resol_mean 0.7
_diffrn_standards_number         none
_diffrn_reflns_number            9617
_diffrn_reflns_av_R_equivalents  0.1203
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_reflns_number_total             2549
_reflns_number_gt                1931
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'VIVALDI (MAATEL)'
_computing_cell_refinement       'lauegen (CCP4)'
_computing_data_reduction        'argonne_boxes, laue4 (Piltz, 2011)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
The variable wavelength nature of the data collection procedure means that
meaningful values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min  0.03  
_diffrn_reflns_sin(theta)/lambda_max  0.86 

_refine_diff_density_max/min is given in Fermi per Angstrom cubed not
electrons per angstrom cubed. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2549
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_restrained_S_all      1.217
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
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_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 0.0262(9) 0.0285(11) 0.0128(7) -0.0043(5) -0.0021(7) 0.0042(6)
H10 0.0180(8) 0.0251(11) 0.0327(10) -0.0091(7) -0.0029(7) -0.0011(6)
H11 0.0334(10) 0.0261(11) 0.0195(7) 0.0069(7) 0.0137(7) 0.0068(8)
H5 0.0450(13) 0.0269(12) 0.0173(8) 0.0021(7) 0.0002(8) 0.0088(8)
H6 0.0202(9) 0.0472(14) 0.0368(11) 0.0046(10) 0.0121(8) 0.0128(9)
H1 0.0253(8) 0.0208(9) 0.0227(8) -0.0017(7) 0.0038(6) 0.0084(7)
H7 0.0443(13) 0.0458(15) 0.0214(9) -0.0121(9) -0.0084(8) 0.0206(11)
H8 0.0344(11) 0.0266(13) 0.0582(15) 0.0178(11) 0.0025(10) -0.0018(9)
H3 0.0271(10) 0.0534(16) 0.0307(10) -0.0176(11) 0.0052(8) 0.0113(10)
H4 0.0506(15) 0.0400(15) 0.0291(11) -0.0059(9) 0.0081(10) -0.0297(11)
H9 0.0218(8) 0.0217(9) 0.0176(7) -0.0009(6) 0.0044(6) 0.0044(6)
O1 0.0106(4) 0.0129(5) 0.0071(3) -0.0023(3) 0.0004(3) 0.0033(3)
O3 0.0117(4) 0.0126(4) 0.0073(3) -0.0011(3) -0.0005(3) 0.0036(3)
O2 0.0137(4) 0.0137(5) 0.0075(3) -0.0005(3) 0.0008(3) 0.0060(3)
C5 0.0084(3) 0.0096(4) 0.0065(3) -0.0008(2) 0.0014(2) 0.0016(2)
C1 0.0065(3) 0.0091(4) 0.0063(3) -0.0004(2) 0.0012(2) 0.0012(2)
N2 0.0081(2) 0.0108(3) 0.0072(2) -0.00151(16) 0.00125(17) 0.00143(16)
N1 0.0110(2) 0.0120(3) 0.0079(2) -0.00118(18) -0.00063(18) 0.00280(18)
C3 0.0118(3) 0.0104(4) 0.0086(3) -0.0023(2) 0.0017(2) -0.0004(2)
C4 0.0073(3) 0.0081(3) 0.0066(3) -0.0001(2) 0.0013(2) 0.0005(2)
C2 0.0105(3) 0.0140(4) 0.0107(3) -0.0002(3) 0.0012(3) 0.0036(3)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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 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) .

_refine_diff_density_max         0.107
_refine_diff_density_min         -0.100
_refine_diff_density_rms         0.023
_database_code_depnum_ccdc_archive 'CCDC 992803'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dmu_suc_100k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N,N-dimethylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(N,N-dimethylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H22 N4 O6'
_chemical_formula_weight         294.32

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   8.483(3)
_cell_length_b                   5.5169(14)
_cell_length_c                   15.415(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.677(8)
_cell_angle_gamma                90.00
_cell_volume                     706.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5991
_cell_measurement_theta_min      6.06
_cell_measurement_theta_max      55.21

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8631
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image Plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9079
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1611
_reflns_number_gt                1468
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0548P)²+0.1069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1611
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.3837(15) 0.745(2) 0.7672(9) 0.030(3) Uiso 1 1 d . . .
H10 H 0.3395(15) -0.007(2) 0.4522(8) 0.029(3) Uiso 1 1 d . . .
H11 H 0.4649(15) 0.162(2) 0.4262(9) 0.031(3) Uiso 1 1 d . . .
H5 H 0.2566(17) 0.998(3) 0.8201(9) 0.039(3) Uiso 1 1 d . . .
H6 H -0.0688(16) 1.159(2) 0.6604(9) 0.036(3) Uiso 1 1 d . . .
H1 H 0.3829(16) 0.581(3) 0.6852(9) 0.039(4) Uiso 1 1 d . . .
H7 H -0.0104(18) 1.061(3) 0.5770(11) 0.045(4) Uiso 1 1 d . . .
H8 H 0.0590(17) 1.308(3) 0.6212(10) 0.044(4) Uiso 1 1 d . . .
H3 H 0.1173(19) 1.175(3) 0.7988(10) 0.048(4) Uiso 1 1 d . . .
H4 H 0.2848(18) 1.233(3) 0.7761(10) 0.047(4) Uiso 1 1 d . . .
H9 H 0.2471(19) 0.539(3) 0.5309(11) 0.054(4) Uiso 1 1 d . . .
O1 O 0.17816(8) 0.76050(13) 0.57846(4) 0.02631(19) Uani 1 1 d . . .
O3 O 0.44678(8) 0.29566(13) 0.61358(4) 0.02637(19) Uani 1 1 d . . .
O2 O 0.27761(8) 0.42346(14) 0.49255(4) 0.0289(2) Uani 1 1 d . . .
C5 C 0.43444(11) 0.08313(17) 0.47599(6) 0.0220(2) Uani 1 1 d . . .
C1 C 0.22332(10) 0.82466(17) 0.65741(6) 0.0207(2) Uani 1 1 d . . .
N2 N 0.14716(9) 1.00578(14) 0.69098(5) 0.0223(2) Uani 1 1 d . . .
N1 N 0.34789(10) 0.71199(16) 0.71040(6) 0.0252(2) Uani 1 1 d . . .
C3 C 0.20635(12) 1.11029(19) 0.77789(6) 0.0255(2) Uani 1 1 d . . .
C4 C 0.38800(10) 0.27683(16) 0.53497(6) 0.0207(2) Uani 1 1 d . . .
C2 C 0.02209(12) 1.1423(2) 0.63276(7) 0.0283(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
O1 0.0287(4) 0.0304(4) 0.0180(3) -0.0028(3) 0.0004(3) 0.0064(3)
O3 0.0299(4) 0.0284(4) 0.0185(3) -0.0025(3) -0.0004(3) 0.0041(3)
O2 0.0333(4) 0.0337(4) 0.0182(3) -0.0015(3) 0.0016(3) 0.0115(3)
C5 0.0226(4) 0.0252(5) 0.0175(4) -0.0005(3) 0.0024(3) 0.0007(4)
C1 0.0204(4) 0.0230(4) 0.0188(4) 0.0002(3) 0.0041(3) -0.0024(3)
N2 0.0215(4) 0.0262(4) 0.0186(4) -0.0017(3) 0.0028(3) 0.0015(3)
N1 0.0274(4) 0.0274(4) 0.0187(4) -0.0026(3) -0.0004(3) 0.0044(3)
C3 0.0281(5) 0.0268(5) 0.0212(5) -0.0042(4) 0.0040(4) -0.0016(4)
C4 0.0201(4) 0.0231(4) 0.0187(4) 0.0015(3) 0.0037(3) -0.0023(3)
C2 0.0261(5) 0.0333(5) 0.0248(5) -0.0004(4) 0.0031(4) 0.0074(4)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2508(12) . ?
O3 C4 1.2179(11) . ?
O2 C4 1.3080(11) . ?
C5 C4 1.5062(13) . ?
C5 C5 1.5144(18) 3_656 ?
C1 N2 1.3487(12) . ?
C1 N1 1.3494(12) . ?
N2 C3 1.4516(12) . ?
N2 C2 1.4536(12) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 C5 112.99(9) . 3_656 ?
O1 C1 N2 120.45(8) . . ?
O1 C1 N1 120.45(8) . . ?
N2 C1 N1 119.09(8) . . ?
C1 N2 C3 123.05(8) . . ?
C1 N2 C2 119.57(8) . . ?
C3 N2 C2 115.90(8) . . ?
O3 C4 O2 123.51(8) . . ?
O3 C4 C5 123.83(8) . . ?
O2 C4 C5 112.66(8) . . ?

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 H9 O1 0.939(18) 1.598(18) 2.5249(11) 168.7(16) .
N1 H1 O3 0.899(15) 2.057(16) 2.9519(12) 173.2(12) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 992804'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dmu_suc_200k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N,N-dimethylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(N,N-dimethylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H22 N4 O6'
_chemical_formula_weight         294.32

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   8.6629(12)
_cell_length_b                   5.6284(6)
_cell_length_c                   15.152(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.948(4)
_cell_angle_gamma                90.00
_cell_volume                     725.34(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    7875
_cell_measurement_theta_min      6.56
_cell_measurement_theta_max      55.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9204
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image Plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9619
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0111
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1664
_reflns_number_gt                1468
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0721P)²+0.0647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1664
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.3805(16) 0.745(2) 0.7673(11) 0.047(4) Uiso 1 1 d . . .
H10 H 0.3421(17) -0.020(3) 0.4579(10) 0.053(4) Uiso 1 1 d . . .
H11 H 0.4616(17) 0.155(3) 0.4237(11) 0.056(4) Uiso 1 1 d . . .
H5 H 0.255(2) 0.993(4) 0.8222(14) 0.086(6) Uiso 1 1 d . . .
H6 H -0.067(2) 1.133(3) 0.6649(13) 0.078(5) Uiso 1 1 d . . .
H1 H 0.3836(18) 0.576(3) 0.6853(11) 0.057(4) Uiso 1 1 d . . .
H7 H -0.021(2) 1.024(3) 0.5792(13) 0.073(5) Uiso 1 1 d . . .
H8 H 0.055(2) 1.266(3) 0.6125(13) 0.081(6) Uiso 1 1 d . . .
H3 H 0.119(3) 1.155(4) 0.7994(16) 0.097(6) Uiso 1 1 d . . .
H4 H 0.285(2) 1.208(4) 0.7748(15) 0.094(6) Uiso 1 1 d . . .
H9 H 0.245(2) 0.522(3) 0.5326(13) 0.073(5) Uiso 1 1 d . . .
O1 O 0.17483(10) 0.73546(15) 0.57906(5) 0.0481(3) Uani 1 1 d . . .
O3 O 0.45031(10) 0.29881(15) 0.61303(5) 0.0489(3) Uani 1 1 d . . .
O2 O 0.27244(10) 0.40025(17) 0.49418(5) 0.0520(3) Uani 1 1 d . . .
C5 C 0.43329(12) 0.0765(2) 0.47667(7) 0.0385(3) Uani 1 1 d . . .
C1 C 0.22052(11) 0.80599(18) 0.65780(7) 0.0351(2) Uani 1 1 d . . .
N2 N 0.14667(10) 0.98701(16) 0.69020(6) 0.0387(2) Uani 1 1 d . . .
N1 N 0.34307(12) 0.70118(19) 0.71139(7) 0.0447(3) Uani 1 1 d . . .
C3 C 0.20373(16) 1.0945(2) 0.77702(8) 0.0475(3) Uani 1 1 d . . .
C4 C 0.38773(11) 0.26892(18) 0.53534(7) 0.0343(2) Uani 1 1 d . . .
C2 C 0.02000(15) 1.1098(3) 0.63165(9) 0.0497(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 0.0509(5) 0.0569(5) 0.0316(4) -0.0084(3) -0.0042(3) 0.0168(4)
O3 0.0520(5) 0.0545(5) 0.0338(4) -0.0088(3) -0.0080(3) 0.0148(4)
O2 0.0572(5) 0.0641(6) 0.0304(4) -0.0052(3) -0.0026(3) 0.0260(4)
C5 0.0383(5) 0.0449(6) 0.0301(5) -0.0023(4) 0.0006(4) 0.0048(4)
C1 0.0341(5) 0.0398(5) 0.0304(5) -0.0008(4) 0.0036(4) -0.0014(4)
N2 0.0375(4) 0.0443(5) 0.0332(4) -0.0047(4) 0.0036(3) 0.0030(4)
N1 0.0472(5) 0.0486(5) 0.0333(5) -0.0056(4) -0.0053(4) 0.0089(4)
C3 0.0511(7) 0.0490(7) 0.0404(6) -0.0129(5) 0.0037(5) -0.0018(5)
C4 0.0330(5) 0.0400(5) 0.0286(5) 0.0017(4) 0.0031(4) -0.0004(4)
C2 0.0471(6) 0.0567(7) 0.0441(6) -0.0011(5) 0.0052(5) 0.0148(5)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2483(13) . ?
O3 C4 1.2105(12) . ?
O2 C4 1.3024(12) . ?
C5 C4 1.5006(14) . ?
C5 C5 1.506(2) 3_656 ?
C1 N1 1.3443(14) . ?
C1 N2 1.3444(14) . ?
N2 C3 1.4470(14) . ?
N2 C2 1.4489(15) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 C5 113.55(10) . 3_656 ?
O1 C1 N1 120.56(10) . . ?
O1 C1 N2 120.23(9) . . ?
N1 C1 N2 119.20(9) . . ?
C1 N2 C3 123.01(9) . . ?
C1 N2 C2 119.71(9) . . ?
C3 N2 C2 116.45(10) . . ?
O3 C4 O2 123.22(9) . . ?
O3 C4 C5 123.83(9) . . ?
O2 C4 C5 112.94(8) . . ?

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 H9 O1 0.96(2) 1.57(2) 2.5183(11) 168.9(17) .
N1 H1 O3 0.909(17) 2.053(17) 2.9562(14) 172.5(14) .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 992805'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dmu_suc_300k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N,N-dimethylurea) butanedioic acid
;
_chemical_name_common            
;
 bis(N,N-dimethylurea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H22 N4 O6'
_chemical_formula_weight         294.32

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   8.797(2)
_cell_length_b                   5.6934(13)
_cell_length_c                   15.059(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.764(7)
_cell_angle_gamma                90.00
_cell_volume                     741.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    5947
_cell_measurement_theta_min      6.55
_cell_measurement_theta_max      55.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8537
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image Plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9568
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1700
_reflns_number_gt                1410
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0917P)²+0.0468P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1700
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1435
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.3762(19) 0.742(3) 0.7661(13) 0.065(5) Uiso 1 1 d . . .
H10 H 0.345(2) -0.028(4) 0.4630(13) 0.084(5) Uiso 1 1 d . . .
H11 H 0.457(2) 0.155(4) 0.4225(16) 0.088(5) Uiso 1 1 d . . .
H5 H 0.255(3) 0.980(6) 0.824(2) 0.140(10) Uiso 1 1 d . . .
H6 H -0.064(3) 1.109(4) 0.6681(18) 0.113(7) Uiso 1 1 d . . .
H1 H 0.387(2) 0.565(4) 0.6846(14) 0.091(6) Uiso 1 1 d . . .
H7 H -0.025(3) 0.993(5) 0.5772(19) 0.118(8) Uiso 1 1 d . . .
H8 H 0.054(3) 1.230(5) 0.606(2) 0.125(9) Uiso 1 1 d . . .
H3 H 0.116(4) 1.127(6) 0.809(2) 0.137(9) Uiso 1 1 d . . .
H4 H 0.286(4) 1.182(7) 0.775(2) 0.153(12) Uiso 1 1 d . . .
H9 H 0.244(3) 0.512(4) 0.5333(17) 0.099(6) Uiso 1 1 d . . .
O1 O 0.17414(13) 0.7193(2) 0.58030(7) 0.0716(4) Uani 1 1 d . . .
O3 O 0.45138(13) 0.2976(2) 0.61269(7) 0.0726(4) Uani 1 1 d . . .
O2 O 0.27126(13) 0.3865(2) 0.49528(7) 0.0734(4) Uani 1 1 d . . .
C5 C 0.43288(16) 0.0728(3) 0.47746(9) 0.0577(4) Uani 1 1 d . . .
C1 C 0.21970(14) 0.7931(2) 0.65836(8) 0.0511(3) Uani 1 1 d . . .
N2 N 0.14785(12) 0.9735(2) 0.68980(7) 0.0572(3) Uani 1 1 d . . .
N1 N 0.34106(15) 0.6923(3) 0.71221(10) 0.0673(4) Uani 1 1 d . . .
C3 C 0.2030(2) 1.0806(3) 0.77677(12) 0.0739(5) Uani 1 1 d . . .
C4 C 0.38793(13) 0.2628(2) 0.53586(8) 0.0500(3) Uani 1 1 d . . .
C2 C 0.0207(2) 1.0882(3) 0.63135(13) 0.0731(5) 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 0.0754(7) 0.0838(7) 0.0483(6) -0.0153(5) -0.0078(5) 0.0264(5)
O3 0.0744(7) 0.0830(8) 0.0507(6) -0.0154(5) -0.0132(5) 0.0243(5)
O2 0.0786(7) 0.0891(8) 0.0459(5) -0.0089(5) -0.0055(5) 0.0351(6)
C5 0.0570(7) 0.0665(8) 0.0458(7) -0.0045(6) 0.0003(6) 0.0104(6)
C1 0.0508(6) 0.0575(7) 0.0432(6) -0.0031(5) 0.0037(5) 0.0000(5)
N2 0.0571(6) 0.0636(6) 0.0490(6) -0.0088(5) 0.0048(5) 0.0047(5)
N1 0.0697(8) 0.0733(8) 0.0510(7) -0.0097(6) -0.0093(6) 0.0138(6)
C3 0.0805(10) 0.0754(10) 0.0628(9) -0.0236(8) 0.0053(8) -0.0029(8)
C4 0.0487(6) 0.0580(7) 0.0414(6) 0.0017(5) 0.0031(5) 0.0020(5)
C2 0.0700(9) 0.0800(11) 0.0677(9) -0.0032(8) 0.0083(8) 0.0216(8)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2422(16) . ?
O3 C4 1.2034(15) . ?
O2 C4 1.2992(15) . ?
C5 C4 1.4931(18) . ?
C5 C5 1.498(3) 3_656 ?
C1 N2 1.3383(17) . ?
C1 N1 1.3428(18) . ?
N2 C2 1.444(2) . ?
N2 C3 1.4440(19) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 C5 114.04(14) . 3_656 ?
O1 C1 N2 120.29(11) . . ?
O1 C1 N1 120.43(13) . . ?
N2 C1 N1 119.28(12) . . ?
C1 N2 C2 119.65(12) . . ?
C1 N2 C3 122.96(12) . . ?
C2 N2 C3 116.93(13) . . ?
O3 C4 O2 123.15(12) . . ?
O3 C4 C5 123.99(11) . . ?
O2 C4 C5 112.85(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
_geom_hbond_site_symmetry_A
O2 H9 O1 0.97(3) 1.56(3) 2.5234(15) 169(2) .
N1 H1 O3 0.96(2) 2.01(2) 2.9633(18) 171.0(18) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 992806'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dmu_fum_100k

_audit_update_record             
;
2011-02-23 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N,N-Dimethylurea) trans-butenedioic acid
;
_chemical_name_common            
;
 bis(N,N-dimethylurea) fumaric acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H20 N4 O6'
_chemical_formula_weight         292.3

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   5.8025(8)
_cell_length_b                   18.158(2)
_cell_length_c                   6.8184(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.019(4)
_cell_angle_gamma                90.00
_cell_volume                     705.14(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6542
_cell_measurement_theta_min      6.09
_cell_measurement_theta_max      55.12

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8436
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9285
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1620
_reflns_number_gt                1286
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0696P)²+0.1012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1620
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H3 H 1.022(4) 0.5732(11) 0.323(3) 0.047(5) Uiso 1 1 d . . .
H2 H 0.860(3) 0.5650(11) 0.479(3) 0.041(5) Uiso 1 1 d . . .
H5 H 1.139(4) 0.6541(10) 0.145(3) 0.044(5) Uiso 1 1 d . . .
H9 H 0.291(3) 0.5391(9) 0.934(3) 0.038(5) Uiso 1 1 d . . .
H1 H 0.497(4) 0.6153(11) 0.535(3) 0.058(6) Uiso 1 1 d . . .
H8 H 0.699(4) 0.7769(12) 0.033(3) 0.059(6) Uiso 1 1 d . . .
H4 H 0.979(4) 0.6190(12) -0.052(3) 0.056(6) Uiso 1 1 d . . .
H6 H 1.034(4) 0.7071(12) -0.031(3) 0.055(6) Uiso 1 1 d . . .
H7 H 0.567(4) 0.7163(13) -0.105(4) 0.070(7) Uiso 1 1 d . . .
H10 H 0.496(4) 0.7356(12) 0.107(4) 0.063(6) Uiso 1 1 d . . .
O1 O 0.56933(17) 0.65460(6) 0.36301(15) 0.0328(3) Uani 1 1 d . . .
N1 N 0.7931(2) 0.67530(6) 0.13011(18) 0.0297(3) Uani 1 1 d . . .
O2 O 0.42679(18) 0.59712(6) 0.65100(16) 0.0345(3) Uani 1 1 d . . .
C2 C 0.5508(2) 0.54593(8) 0.7583(2) 0.0294(3) Uani 1 1 d . . .
C1 C 0.7489(2) 0.63899(8) 0.2910(2) 0.0280(3) Uani 1 1 d . . .
O3 O 0.73649(19) 0.52107(6) 0.72523(16) 0.0356(3) Uani 1 1 d . . .
C3 C 0.4435(3) 0.52189(8) 0.9293(2) 0.0305(3) Uani 1 1 d . . .
N2 N 0.8989(2) 0.58624(7) 0.3747(2) 0.0319(3) Uani 1 1 d . . .
C5 C 0.6276(3) 0.72983(8) 0.0300(2) 0.0324(3) Uani 1 1 d . . .
C4 C 1.0017(3) 0.66197(10) 0.0450(3) 0.0364(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 0.0286(5) 0.0339(6) 0.0377(6) 0.0039(4) 0.0112(4) 0.0054(4)
N1 0.0238(6) 0.0308(6) 0.0355(7) 0.0028(5) 0.0082(5) 0.0014(4)
O2 0.0315(6) 0.0381(6) 0.0351(6) 0.0053(5) 0.0096(5) 0.0072(4)
C2 0.0290(7) 0.0281(7) 0.0313(7) -0.0043(6) 0.0061(6) 0.0008(5)
C1 0.0238(6) 0.0273(6) 0.0324(7) -0.0026(6) 0.0042(5) -0.0006(5)
O3 0.0342(6) 0.0368(6) 0.0386(6) 0.0043(5) 0.0138(5) 0.0083(4)
C3 0.0277(7) 0.0309(7) 0.0341(7) -0.0041(6) 0.0086(6) 0.0009(5)
N2 0.0274(6) 0.0339(7) 0.0353(7) 0.0039(5) 0.0079(5) 0.0053(5)
C5 0.0290(7) 0.0305(7) 0.0381(8) 0.0061(6) 0.0070(6) 0.0018(6)
C4 0.0273(8) 0.0449(9) 0.0387(9) 0.0003(7) 0.0106(7) 0.0036(6)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2659(17) . ?
N1 C1 1.3456(19) . ?
N1 C5 1.4552(18) . ?
N1 C4 1.4596(19) . ?
O2 C2 1.3098(18) . ?
C2 O3 1.2282(18) . ?
C2 C3 1.488(2) . ?
C1 N2 1.3459(18) . ?
C3 C3 1.323(3) 3_667 ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 120.28(12) . . ?
C1 N1 C4 123.01(12) . . ?
C5 N1 C4 116.70(12) . . ?
O3 C2 O2 124.46(14) . . ?
O3 C2 C3 123.30(13) . . ?
O2 C2 C3 112.23(12) . . ?
O1 C1 N1 120.38(12) . . ?
O1 C1 N2 120.55(13) . . ?
N1 C1 N2 119.07(13) . . ?
C3 C3 C2 121.59(17) 3_667 . ?

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 O1 1.01(2) 1.50(2) 2.5000(15) 169(2) .
N2 H2 O3 0.88(2) 2.10(2) 2.9769(18) 174.1(17) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 992807'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dmu_fum_200k

_audit_update_record             
;
2011-02-23 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N,N-Dimethylurea) trans-butenedioic acid
;
_chemical_name_common            
;
 bis(N,N-dimethylurea) fumaric acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H20 N4 O6'
_chemical_formula_weight         292.3

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   5.8640(5)
_cell_length_b                   18.2369(11)
_cell_length_c                   6.8458(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.330(3)
_cell_angle_gamma                90.00
_cell_volume                     717.83(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    7004
_cell_measurement_theta_min      6.07
_cell_measurement_theta_max      55.08

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7597
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9445
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         27.46
_reflns_number_total             1645
_reflns_number_gt                1317
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0688P)²+0.0926P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1645
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H3 H 1.023(4) 0.5750(10) 0.337(3) 0.061(5) Uiso 1 1 d . . .
H2 H 0.874(3) 0.5665(10) 0.489(3) 0.054(5) Uiso 1 1 d . . .
H5 H 1.147(4) 0.6537(11) 0.155(3) 0.072(6) Uiso 1 1 d . . .
H9 H 0.293(3) 0.5389(10) 0.933(3) 0.063(5) Uiso 1 1 d . . .
H1 H 0.510(4) 0.6149(11) 0.541(3) 0.075(6) Uiso 1 1 d . . .
H8 H 0.708(4) 0.7745(14) 0.050(4) 0.095(7) Uiso 1 1 d . . .
H4 H 0.983(5) 0.6200(17) -0.038(5) 0.113(9) Uiso 1 1 d . . .
H6 H 1.039(4) 0.7014(14) -0.028(4) 0.097(8) Uiso 1 1 d . . .
H7 H 0.586(5) 0.7174(15) -0.096(5) 0.113(9) Uiso 1 1 d . . .
H10 H 0.512(4) 0.7368(13) 0.121(4) 0.091(7) Uiso 1 1 d . . .
O1 O 0.57930(17) 0.65464(5) 0.36994(15) 0.0464(3) Uani 1 1 d . . .
N1 N 0.80053(19) 0.67401(6) 0.13949(17) 0.0413(3) Uani 1 1 d . . .
O2 O 0.43434(19) 0.59703(6) 0.65367(16) 0.0510(3) Uani 1 1 d . . .
C2 C 0.5551(2) 0.54600(7) 0.7614(2) 0.0401(3) Uani 1 1 d . . .
C1 C 0.7572(2) 0.63868(7) 0.30033(19) 0.0371(3) Uani 1 1 d . . .
O3 O 0.73875(19) 0.52133(6) 0.73150(16) 0.0526(3) Uani 1 1 d . . .
C3 C 0.4462(3) 0.52178(7) 0.9290(2) 0.0424(3) Uani 1 1 d . . .
N2 N 0.9047(2) 0.58633(7) 0.3856(2) 0.0461(3) Uani 1 1 d . . .
C5 C 0.6393(3) 0.72921(9) 0.0414(3) 0.0475(4) Uani 1 1 d . . .
C4 C 1.0066(3) 0.66016(11) 0.0570(3) 0.0541(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 0.0463(6) 0.0441(5) 0.0513(6) 0.0092(4) 0.0158(4) 0.0121(4)
N1 0.0370(6) 0.0396(6) 0.0477(6) 0.0048(5) 0.0096(5) 0.0014(4)
O2 0.0497(6) 0.0540(6) 0.0505(6) 0.0117(5) 0.0131(5) 0.0143(4)
C2 0.0436(7) 0.0353(6) 0.0408(7) -0.0041(5) 0.0069(5) 0.0034(5)
C1 0.0354(6) 0.0324(6) 0.0420(7) -0.0014(5) 0.0038(5) 0.0002(5)
O3 0.0545(6) 0.0524(6) 0.0549(6) 0.0112(5) 0.0206(5) 0.0164(5)
C3 0.0449(8) 0.0398(7) 0.0432(7) -0.0028(5) 0.0109(6) 0.0040(5)
N2 0.0422(7) 0.0453(7) 0.0508(7) 0.0089(6) 0.0089(5) 0.0106(5)
C5 0.0478(8) 0.0402(7) 0.0543(9) 0.0117(6) 0.0095(7) 0.0031(6)
C4 0.0429(8) 0.0661(10) 0.0557(9) 0.0026(8) 0.0157(7) 0.0046(7)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2630(16) . ?
N1 C1 1.3425(18) . ?
N1 C5 1.4522(18) . ?
N1 C4 1.4531(19) . ?
O2 C2 1.3064(17) . ?
C2 O3 1.2208(17) . ?
C2 C3 1.486(2) . ?
C1 N2 1.3423(17) . ?
C3 C3 1.317(3) 3_667 ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 120.05(12) . . ?
C1 N1 C4 122.77(12) . . ?
C5 N1 C4 117.18(12) . . ?
O3 C2 O2 124.47(13) . . ?
O3 C2 C3 123.19(13) . . ?
O2 C2 C3 112.33(11) . . ?
O1 C1 N2 120.62(12) . . ?
O1 C1 N1 120.15(12) . . ?
N2 C1 N1 119.22(13) . . ?
C3 C3 C2 122.20(17) 3_667 . ?

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 O1 1.01(2) 1.50(2) 2.4996(14) 167(2) .
N2 H2 O3 0.85(2) 2.14(2) 2.9776(18) 170.8(17) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 992808'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dmu_fum_300k

_audit_update_record             
;
2011-02-23 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(N,N-Dimethylurea) trans-butenedioic acid
;
_chemical_name_common            
;
 bis(N,N-dimethylurea) fumaric acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H20 N4 O6'
_chemical_formula_weight         292.3

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   5.924(4)
_cell_length_b                   18.376(9)
_cell_length_c                   6.873(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.293(5)
_cell_angle_gamma                90.00
_cell_volume                     733.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    5453
_cell_measurement_theta_min      6.04
_cell_measurement_theta_max      55.16

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7014
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9713
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1674
_reflns_number_gt                1029
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0906P)²+0.0632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1674
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H3 H 1.033(5) 0.5784(15) 0.340(4) 0.100(9) Uiso 1 1 d . . .
H2 H 0.880(4) 0.5678(15) 0.502(4) 0.090(8) Uiso 1 1 d . . .
H5 H 1.149(7) 0.6561(18) 0.166(6) 0.132(11) Uiso 1 1 d . . .
H9 H 0.297(5) 0.5365(15) 0.935(4) 0.106(9) Uiso 1 1 d . . .
H1 H 0.528(6) 0.6140(18) 0.541(5) 0.128(10) Uiso 1 1 d . . .
H8 H 0.726(7) 0.775(2) 0.063(5) 0.139(12) Uiso 1 1 d . . .
H4 H 1.000(8) 0.620(3) -0.031(7) 0.170(15) Uiso 1 1 d . . .
H6 H 1.035(7) 0.695(2) -0.025(6) 0.154(14) Uiso 1 1 d . . .
H7 H 0.595(7) 0.717(2) -0.078(7) 0.152(14) Uiso 1 1 d . . .
H10 H 0.526(7) 0.7357(17) 0.135(5) 0.130(11) Uiso 1 1 d . . .
O1 O 0.5893(3) 0.65374(8) 0.3769(2) 0.0754(5) Uani 1 1 d . . .
N1 N 0.8100(3) 0.67334(9) 0.1503(3) 0.0656(5) Uani 1 1 d . . .
O2 O 0.4407(3) 0.59601(9) 0.6564(2) 0.0832(5) Uani 1 1 d . . .
C2 C 0.5589(4) 0.54605(11) 0.7652(3) 0.0641(5) Uani 1 1 d . . .
C1 C 0.7660(3) 0.63838(10) 0.3093(3) 0.0589(5) Uani 1 1 d . . .
O3 O 0.7423(3) 0.52219(9) 0.7381(2) 0.0851(6) Uani 1 1 d . . .
C3 C 0.4481(4) 0.52125(11) 0.9294(3) 0.0682(6) Uani 1 1 d . . .
N2 N 0.9116(4) 0.58678(11) 0.3951(4) 0.0759(6) Uani 1 1 d . . .
C5 C 0.6510(5) 0.72860(15) 0.0541(5) 0.0785(7) Uani 1 1 d . . .
C4 C 1.0130(5) 0.65967(19) 0.0685(5) 0.0862(8) 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 0.0756(10) 0.0742(10) 0.0809(10) 0.0171(7) 0.0267(8) 0.0199(7)
N1 0.0610(10) 0.0627(10) 0.0744(11) 0.0094(8) 0.0167(8) 0.0012(7)
O2 0.0811(10) 0.0889(11) 0.0821(11) 0.0217(8) 0.0221(8) 0.0229(8)
C2 0.0683(12) 0.0591(11) 0.0653(12) -0.0041(9) 0.0143(9) 0.0056(9)
C1 0.0551(10) 0.0522(10) 0.0679(11) 0.0007(9) 0.0081(8) 0.0022(8)
O3 0.0898(11) 0.0863(11) 0.0853(11) 0.0205(8) 0.0324(9) 0.0270(9)
C3 0.0712(14) 0.0657(12) 0.0692(12) -0.0015(9) 0.0173(10) 0.0073(10)
N2 0.0706(12) 0.0749(12) 0.0824(13) 0.0167(10) 0.0155(10) 0.0177(9)
C5 0.0793(16) 0.0680(14) 0.0883(18) 0.0228(12) 0.0166(13) 0.0082(11)
C4 0.0718(16) 0.103(2) 0.0888(18) 0.0043(16) 0.0282(14) 0.0034(14)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.258(2) . ?
N1 C1 1.337(3) . ?
N1 C4 1.446(3) . ?
N1 C5 1.453(3) . ?
O2 C2 1.299(3) . ?
C2 O3 1.219(3) . ?
C2 C3 1.484(3) . ?
C1 N2 1.338(3) . ?
C3 C3 1.302(4) 3_667 ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 123.0(2) . . ?
C1 N1 C5 119.66(19) . . ?
C4 N1 C5 117.3(2) . . ?
O3 C2 O2 124.2(2) . . ?
O3 C2 C3 123.08(19) . . ?
O2 C2 C3 112.70(19) . . ?
O1 C1 N1 120.24(17) . . ?
O1 C1 N2 120.5(2) . . ?
N1 C1 N2 119.2(2) . . ?
C3 C3 C2 122.4(3) 3_667 . ?

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 O1 1.08(4) 1.45(4) 2.501(2) 163(3) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 992809'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_usuc_100

# start Validation Reply Form
_vrf_TYPE031_usuc_100            
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
_vrf_PLAT051_usuc_100            
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.40 %     
RESPONSE: The differences arise from the fact that these are neutron data.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(urea) butanedioic acid
;
_chemical_name_common            
;
 bis(urea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H14 N4 O6'
_chemical_formula_weight         238.20

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.7100(6)
_cell_length_b                   7.9700(10)
_cell_length_c                   12.1600(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.160(4)
_cell_angle_gamma                90.00
_cell_volume                     550.19(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          3.0
_exptl_crystal_size_mid          1.2
_exptl_crystal_size_min          0.4
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             120
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
For peak integration a local UB matrix was refined for each pattern, 
using approximately 250 reflections.
Hence _cell_measurement_reflns_used      250

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.8-5.2 Angstroms.
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.80-5.20
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ILL reactor source, thermal guide'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  VIVALDI
_diffrn_measurement_method       'Laue patterns at 10 orientations'
_diffrn_detector_area_resol_mean 0.7
_diffrn_standards_number         none
_diffrn_reflns_number            7869
_diffrn_reflns_av_R_equivalents  0.1318
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_reflns_number_total             1403
_reflns_number_gt                1087
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'VIVALDI (MAATEL)'
_computing_cell_refinement       'lauegen (CCP4)'
_computing_data_reduction        'argonne_boxes, laue4 (Piltz, 2011)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
The variable wavelength nature of the data collection procedure means that
meaningful values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min  0.03  
_diffrn_reflns_sin(theta)/lambda_max  0.82 

_refine_diff_density_max/min is given in Fermi per Angstrom cubed not
electrons per angstrom cubed. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1403
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.258
_refine_ls_restrained_S_all      1.258
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.9790(6) 0.6299(3) 0.4054(2) 0.0350(7) Uani 1 1 d . . .
H7 H -0.0562(5) 0.4450(3) 0.09570(18) 0.0314(7) Uani 1 1 d . . .
H3 H 0.8085(5) 0.4473(3) 0.4081(2) 0.0327(7) Uani 1 1 d . . .
H6 H 0.0717(5) 0.4284(3) 0.23423(19) 0.0326(6) Uani 1 1 d . . .
H4 H 0.5425(6) 0.6950(3) 0.1930(2) 0.0399(8) Uani 1 1 d . . .
H1 H 0.4447(5) 0.7746(3) 0.49578(18) 0.0281(6) Uani 1 1 d . . .
H5 H 0.4067(6) 0.5824(4) 0.29064(19) 0.0402(8) Uani 1 1 d . . .
O1 O 0.7439(3) 0.64923(13) 0.62134(9) 0.0191(3) Uani 1 1 d . . .
O3 O 0.2481(3) 0.62740(13) 0.03424(9) 0.0191(3) Uani 1 1 d . . .
O2 O 0.5608(3) 0.70478(14) 0.45378(9) 0.0195(3) Uani 1 1 d . . .
C2 C 0.9044(2) 0.54116(10) 0.46098(8) 0.0152(3) Uani 1 1 d . . .
N2 N 0.06509(18) 0.47958(8) 0.15827(6) 0.0195(2) Uani 1 1 d . . .
C1 C 0.7306(2) 0.63703(10) 0.52057(8) 0.0140(3) Uani 1 1 d . . .
C3 C 0.2427(2) 0.57576(11) 0.13214(8) 0.0162(3) Uani 1 1 d . . .
N1 N 0.41232(19) 0.61815(11) 0.21208(6) 0.0290(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
H2 0.041(2) 0.0365(10) 0.0287(11) 0.0117(8) 0.0075(12) 0.0057(10)
H7 0.0296(18) 0.0380(10) 0.0251(10) 0.0037(7) -0.0039(11) -0.0096(9)
H3 0.0321(18) 0.0350(10) 0.0295(11) -0.0115(8) -0.0034(11) 0.0016(9)
H6 0.0368(18) 0.0408(10) 0.0203(9) 0.0084(7) 0.0041(10) -0.0074(10)
H4 0.038(2) 0.0518(13) 0.0285(11) 0.0055(9) -0.0049(12) -0.0225(13)
H1 0.0273(17) 0.0320(9) 0.0246(10) -0.0028(7) 0.0002(10) 0.0080(9)
H5 0.041(2) 0.0597(14) 0.0181(10) 0.0070(9) -0.0039(12) -0.0086(13)
O1 0.0205(9) 0.0252(5) 0.0113(5) 0.0000(3) 0.0008(5) 0.0073(4)
O3 0.0202(9) 0.0246(4) 0.0118(5) 0.0037(3) -0.0019(5) -0.0081(4)
O2 0.0215(9) 0.0244(5) 0.0118(4) -0.0012(4) -0.0014(5) 0.0092(5)
C2 0.0170(7) 0.0168(3) 0.0117(4) 0.0006(3) 0.0017(4) 0.0032(3)
N2 0.0200(6) 0.0231(3) 0.0148(3) 0.0040(2) -0.0012(3) -0.0052(3)
C1 0.0152(7) 0.0160(3) 0.0107(4) 0.0004(3) 0.0005(4) 0.0020(3)
C3 0.0175(7) 0.0188(3) 0.0116(4) 0.0020(3) -0.0009(4) -0.0047(4)
N1 0.0312(7) 0.0403(4) 0.0136(3) 0.0060(3) -0.0061(4) -0.0183(4)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2235(16) . ?
O3 C3 1.2631(15) . ?
O2 C1 1.3124(13) . ?
O2 H1 1.040(3) . ?
C2 C1 1.4995(17) . ?
C2 C2 1.5166(18) 3_766 ?
C2 H2 1.096(3) . ?
C2 H3 1.094(2) . ?
N2 C3 1.3366(16) . ?
N2 H7 1.011(2) . ?
N2 H6 1.007(2) . ?
C3 N1 1.3397(11) . ?
N1 H4 1.009(3) . ?
N1 H5 1.001(2) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H1 112.56(15) . . ?
C1 C2 C2 112.78(10) . 3_766 ?
C1 C2 H2 106.89(17) . . ?
C2 C2 H2 111.4(2) 3_766 . ?
C1 C2 H3 108.48(19) . . ?
C2 C2 H3 110.70(15) 3_766 . ?
H2 C2 H3 106.3(2) . . ?
C3 N2 H7 116.99(16) . . ?
C3 N2 H6 119.71(17) . . ?
H7 N2 H6 122.4(2) . . ?
O1 C1 O2 123.32(13) . . ?
O1 C1 C2 123.47(9) . . ?
O2 C1 C2 113.21(10) . . ?
O3 C3 N2 120.43(9) . . ?
O3 C3 N1 120.87(11) . . ?
N2 C3 N1 118.69(9) . . ?
C3 N1 H4 118.66(15) . . ?
C3 N1 H5 121.74(19) . . ?
H4 N1 H5 119.5(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 H1 O3 1.040(3) 1.484(3) 2.512(2) 168.4(2) 4_576
N1 H4 O1 1.009(3) 1.959(3) 2.9473(17) 165.61(19) 4_575
N2 H6 O1 1.007(2) 2.044(2) 2.9662(12) 151.2(3) 3_666
N1 H5 O2 1.001(2) 2.299(3) 3.0494(13) 130.9(2) .

_refine_diff_density_max         0.646
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.141
_database_code_depnum_ccdc_archive 'CCDC 992810'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_usuc_200

# start Validation Reply Form
_vrf_TYPE031_usuc_200            
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
_vrf_PLAT051_usuc_200            
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.40 %     
RESPONSE: The differences arise from the fact that these are neutron data.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(urea) butanedioic acid
;
_chemical_name_common            
;
 bis(urea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H14 N4 O6'
_chemical_formula_weight         238.20

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.6700(6)
_cell_length_b                   8.1200(10)
_cell_length_c                   12.2200(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.380(4)
_cell_angle_gamma                90.00
_cell_volume                     559.13(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          3.0
_exptl_crystal_size_mid          1.2
_exptl_crystal_size_min          0.4
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             120
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
For peak integration a local UB matrix was refined for each pattern, 
using approximately 250 reflections.
Hence _cell_measurement_reflns_used      250

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.8-5.2 Angstroms.
;

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.80-5.20
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ILL reactor source, thermal guide'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  VIVALDI
_diffrn_measurement_method       'Laue patterns at 10 orientations'
_diffrn_detector_area_resol_mean 0.7
_diffrn_standards_number         none
_diffrn_reflns_number            4829
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_reflns_number_total             826
_reflns_number_gt                659
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'VIVALDI (MAATEL)'
_computing_cell_refinement       'lauegen (CCP4)'
_computing_data_reduction        'argonne_boxes, laue4 (Piltz, 2011)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
The variable wavelength nature of the data collection procedure means that
meaningful values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min  0.03  
_diffrn_reflns_sin(theta)/lambda_max  0.65 

_refine_diff_density_max/min is given in Fermi per Angstrom cubed not
electrons per angstrom cubed. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         826
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0691
_refine_ls_wR_factor_gt          0.0642
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_restrained_S_all      1.235
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.9822(7) 0.6290(4) 0.4071(3) 0.0523(9) Uani 1 1 d . . .
H7 H -0.0534(6) 0.4460(4) 0.0950(2) 0.0474(9) Uani 1 1 d . . .
H3 H 0.8058(6) 0.4518(4) 0.4075(3) 0.0511(9) Uani 1 1 d . . .
H6 H 0.0721(6) 0.4326(4) 0.2332(2) 0.0480(8) Uani 1 1 d . . .
H4 H 0.5404(8) 0.6995(5) 0.1937(3) 0.0636(11) Uani 1 1 d . . .
H1 H 0.4441(6) 0.7745(4) 0.4965(2) 0.0425(8) Uani 1 1 d . . .
H5 H 0.4043(7) 0.5879(5) 0.2906(2) 0.0601(10) Uani 1 1 d . . .
O1 O 0.7405(3) 0.64468(18) 0.62118(12) 0.0359(5) Uani 1 1 d . . .
O3 O 0.2469(4) 0.62980(18) 0.03515(12) 0.0361(5) Uani 1 1 d . . .
O2 O 0.5639(4) 0.7072(2) 0.45443(12) 0.0368(5) Uani 1 1 d . . .
C2 C 0.9047(3) 0.54192(15) 0.46136(10) 0.0282(4) Uani 1 1 d . . .
N2 N 0.0642(2) 0.48289(11) 0.15808(9) 0.0356(4) Uani 1 1 d . . .
C1 C 0.7310(3) 0.63653(14) 0.52092(10) 0.0257(4) Uani 1 1 d . . .
C3 C 0.2413(3) 0.57947(15) 0.13235(10) 0.0303(4) Uani 1 1 d . . .
N1 N 0.4102(3) 0.62325(17) 0.21248(8) 0.0522(5) 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 0.057(3) 0.0597(17) 0.0427(16) 0.0168(13) 0.0156(17) 0.0120(14)
H7 0.043(2) 0.0574(17) 0.0398(16) 0.0080(11) -0.0047(16) -0.0149(13)
H3 0.052(2) 0.0561(15) 0.0435(16) -0.0164(12) -0.0050(15) 0.0065(14)
H6 0.052(2) 0.0597(16) 0.0325(15) 0.0087(12) 0.0055(14) -0.0085(15)
H4 0.066(3) 0.079(2) 0.0418(17) 0.0099(15) -0.0096(17) -0.032(2)
H1 0.040(2) 0.0531(14) 0.0327(14) -0.0034(11) -0.0010(14) 0.0154(15)
H5 0.062(3) 0.090(2) 0.0258(15) 0.0097(14) -0.0037(15) -0.0107(19)
O1 0.0384(12) 0.0479(8) 0.0210(7) 0.0021(5) 0.0021(8) 0.0145(7)
O3 0.0384(13) 0.0478(8) 0.0205(8) 0.0069(5) -0.0035(7) -0.0170(7)
O2 0.0395(13) 0.0486(8) 0.0211(8) -0.0040(6) -0.0018(9) 0.0189(9)
C2 0.0298(10) 0.0342(6) 0.0209(6) 0.0006(4) 0.0038(7) 0.0062(6)
N2 0.0353(9) 0.0439(5) 0.0268(6) 0.0072(4) 0.0005(6) -0.0103(4)
C1 0.0269(10) 0.0298(5) 0.0200(6) 0.0000(4) 0.0008(6) 0.0038(5)
C3 0.0330(10) 0.0370(6) 0.0199(6) 0.0041(4) -0.0018(6) -0.0080(6)
N1 0.0530(10) 0.0770(8) 0.0234(6) 0.0105(5) -0.0093(6) -0.0325(7)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.222(2) . ?
O3 C3 1.2599(19) . ?
O2 C1 1.310(2) . ?
O2 H1 1.050(5) . ?
C2 C1 1.500(2) . ?
C2 C2 1.515(2) 3_766 ?
C2 H2 1.094(4) . ?
C2 H3 1.096(3) . ?
N2 C3 1.3388(19) . ?
N2 H7 1.007(3) . ?
N2 H6 1.002(3) . ?
C3 N1 1.3394(15) . ?
N1 H4 1.009(5) . ?
N1 H5 1.001(3) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H1 112.8(2) . . ?
C1 C2 C2 112.88(13) . 3_766 ?
C1 C2 H2 107.0(2) . . ?
C2 C2 H2 111.2(2) 3_766 . ?
C1 C2 H3 108.3(2) . . ?
C2 C2 H3 110.9(2) 3_766 . ?
H2 C2 H3 106.3(3) . . ?
C3 N2 H7 116.4(2) . . ?
C3 N2 H6 119.7(2) . . ?
H7 N2 H6 122.6(3) . . ?
O1 C1 O2 123.10(17) . . ?
O1 C1 C2 123.80(13) . . ?
O2 C1 C2 113.08(13) . . ?
O3 C3 N2 120.64(12) . . ?
O3 C3 N1 120.81(15) . . ?
N2 C3 N1 118.54(12) . . ?
C3 N1 H4 118.6(2) . . ?
C3 N1 H5 121.6(3) . . ?
H4 N1 H5 119.7(3) . . ?

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 1.050(5) 1.481(4) 2.520(3) 169.0(2) 4_576
N1 H4 O1 1.009(5) 1.974(5) 2.961(2) 165.2(3) 4_575
N2 H6 O1 1.002(3) 2.066(3) 2.9853(17) 151.6(3) 3_666
N1 H5 O2 1.001(3) 2.316(3) 3.0648(18) 130.8(3) .

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 992811'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_usuc_rt

# start Validation Reply Form
_vrf_TYPE031_usuc_rt             
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
_vrf_PLAT051_usuc_rt             
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.30 %     
RESPONSE: The differences arise from the fact that these are neutron data.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(urea) butanedioic acid
;
_chemical_name_common            
;
 bis(urea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H14 N4 O6'
_chemical_formula_weight         238.20

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.6400(6)
_cell_length_b                   8.2600(10)
_cell_length_c                   12.2800(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.660(4)
_cell_angle_gamma                90.00
_cell_volume                     568.22(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          3.0
_exptl_crystal_size_mid          1.2
_exptl_crystal_size_min          0.4
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             120
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
For peak integration a local UB matrix was refined for each pattern, 
using approximately 250 reflections.
Hence _cell_measurement_reflns_used      250

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.8-5.2 Angstroms.
;

_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.80-5.20
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ILL reactor source, thermal guide'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  VIVALDI
_diffrn_measurement_method       'Laue patterns at 10 orientations'
_diffrn_detector_area_resol_mean 0.7
_diffrn_standards_number         none
_diffrn_reflns_number            8028
_diffrn_reflns_av_R_equivalents  0.1155
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_number_total             1049
_reflns_number_gt                791
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'VIVALDI (MAATEL)'
_computing_cell_refinement       'lauegen (CCP4)'
_computing_data_reduction        'argonne_boxes, laue4 (Piltz, 2011)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
The variable wavelength nature of the data collection procedure means that
meaningful values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min  0.03  
_diffrn_reflns_sin(theta)/lambda_max  0.69 

_refine_diff_density_max/min is given in Fermi per Angstrom cubed not
electrons per angstrom cubed. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.005(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1049
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.368
_refine_ls_restrained_S_all      1.368
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.9843(6) 0.6274(4) 0.4086(2) 0.0731(9) Uani 1 1 d . . .
H7 H -0.0521(5) 0.4479(4) 0.0947(2) 0.0639(8) Uani 1 1 d . . .
H3 H 0.8040(6) 0.4578(4) 0.4073(3) 0.0727(9) Uani 1 1 d . . .
H6 H 0.0741(6) 0.4370(4) 0.2319(2) 0.0680(8) Uani 1 1 d . . .
H4 H 0.5393(7) 0.7018(6) 0.1947(3) 0.0887(12) Uani 1 1 d . . .
H1 H 0.4480(6) 0.7745(4) 0.4969(2) 0.0587(8) Uani 1 1 d . . .
H5 H 0.4045(7) 0.5917(6) 0.2898(2) 0.0867(11) Uani 1 1 d . . .
O1 O 0.7390(3) 0.6410(2) 0.62071(11) 0.0541(5) Uani 1 1 d . . .
O3 O 0.2468(3) 0.63132(19) 0.03596(11) 0.0540(5) Uani 1 1 d . . .
O2 O 0.5667(3) 0.7089(2) 0.45543(12) 0.0551(5) Uani 1 1 d . . .
C2 C 0.9050(3) 0.54271(14) 0.46177(10) 0.0419(4) Uani 1 1 d . . .
N2 N 0.0655(2) 0.48559(12) 0.15746(9) 0.0527(3) Uani 1 1 d . . .
C1 C 0.7312(2) 0.63581(13) 0.52109(9) 0.0383(4) Uani 1 1 d . . .
C3 C 0.2405(2) 0.58205(15) 0.13255(9) 0.0450(4) Uani 1 1 d . . .
N1 N 0.4077(3) 0.62654(17) 0.21278(8) 0.0770(5) 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 0.080(2) 0.0807(19) 0.0619(16) 0.0235(15) 0.0233(17) 0.0199(16)
H7 0.063(2) 0.0756(17) 0.0513(14) 0.0091(11) -0.0019(14) -0.0187(13)
H3 0.071(2) 0.0829(17) 0.0595(15) -0.0261(14) -0.0131(16) 0.0165(15)
H6 0.078(2) 0.0810(18) 0.0446(14) 0.0123(12) 0.0070(15) -0.0134(16)
H4 0.084(3) 0.121(3) 0.0550(17) 0.0147(18) -0.0165(18) -0.047(2)
H1 0.064(2) 0.0682(14) 0.0407(13) -0.0045(10) -0.0059(13) 0.0198(14)
H5 0.085(3) 0.135(3) 0.0366(14) 0.0144(16) -0.0069(15) -0.018(2)
O1 0.0596(13) 0.0716(9) 0.0306(7) 0.0035(6) 0.0022(7) 0.0214(8)
O3 0.0586(12) 0.0693(9) 0.0311(7) 0.0112(6) -0.0073(7) -0.0268(7)
O2 0.0593(13) 0.0723(9) 0.0313(7) -0.0027(7) -0.0049(8) 0.0275(9)
C2 0.0443(9) 0.0490(6) 0.0317(5) 0.0011(5) 0.0008(6) 0.0103(6)
N2 0.0543(8) 0.0647(6) 0.0379(5) 0.0108(4) -0.0005(5) -0.0145(4)
C1 0.0415(8) 0.0428(5) 0.0296(5) 0.0011(4) 0.0002(5) 0.0051(5)
C3 0.0497(10) 0.0533(6) 0.0300(5) 0.0057(4) -0.0041(6) -0.0108(6)
N1 0.0816(10) 0.1090(9) 0.0351(6) 0.0144(5) -0.0166(6) -0.0457(7)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2198(17) . ?
O3 C3 1.2584(17) . ?
O2 C1 1.3047(17) . ?
O2 H1 1.039(5) . ?
C2 C1 1.4993(19) . ?
C2 C2 1.515(2) 3_766 ?
C2 H2 1.088(4) . ?
C2 H3 1.084(3) . ?
N2 C3 1.3316(17) . ?
N2 H7 1.006(3) . ?
N2 H6 0.995(3) . ?
C3 N1 1.3340(14) . ?
N1 H4 1.013(5) . ?
N1 H5 0.990(3) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H1 113.02(19) . . ?
C1 C2 C2 113.15(13) . 3_766 ?
C1 C2 H2 107.40(19) . . ?
C2 C2 H2 111.2(2) 3_766 . ?
C1 C2 H3 107.8(2) . . ?
C2 C2 H3 111.4(2) 3_766 . ?
H2 C2 H3 105.6(3) . . ?
C3 N2 H7 116.71(19) . . ?
C3 N2 H6 119.6(2) . . ?
H7 N2 H6 122.5(3) . . ?
O1 C1 O2 122.94(16) . . ?
O1 C1 C2 123.77(12) . . ?
O2 C1 C2 113.28(12) . . ?
O3 C3 N2 120.85(11) . . ?
O3 C3 N1 120.81(13) . . ?
N2 C3 N1 118.33(11) . . ?
C3 N1 H4 118.70(19) . . ?
C3 N1 H5 122.4(3) . . ?
H4 N1 H5 118.9(3) . . ?

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 1.039(5) 1.500(4) 2.527(3) 169.0(2) 4_576
N1 H4 O1 1.013(5) 2.004(5) 2.991(2) 164.2(3) 4_575

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.077
_database_code_depnum_ccdc_archive 'CCDC 992812'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_u_suc_100k

_audit_update_record             
;
2012-03-19 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(urea) butanedioic acid
;
_chemical_name_common            
;
 bis(urea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H14 N4 O6'
_chemical_formula_weight         238.21

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.7109(7)
_cell_length_b                   7.9698(11)
_cell_length_c                   12.1580(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.160(4)
_cell_angle_gamma                90.00
_cell_volume                     550.17(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5241
_cell_measurement_theta_min      6.12
_cell_measurement_theta_max      55.20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8819
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
'Rigaku R-AXIS RAPID IP Image Plate diffractometer'
;
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7014
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.46
_reflns_number_total             1255
_reflns_number_gt                1085
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.0856P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1255
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
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)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 992813'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_u_suc_200k

_audit_update_record             
;
2012-03-19 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(urea) butanedioic acid
;
_chemical_name_common            
;
 bis(urea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H14 N4 O6'
_chemical_formula_weight         238.21

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.6706(5)
_cell_length_b                   8.1227(7)
_cell_length_c                   12.2182(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.375(3)
_cell_angle_gamma                90.00
_cell_volume                     559.30(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    5873
_cell_measurement_theta_min      6.03
_cell_measurement_theta_max      55.19

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9251
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
'Rigaku R-AXIS RAPID IP Image Plate diffractometer'
;
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7340
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1280
_reflns_number_gt                1065
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0502P)²+0.0690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1280
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.975(2) 0.6173(17) 0.4133(12) 0.043(3) Uiso 1 1 d . . .
H7 H -0.039(3) 0.4516(19) 0.1036(13) 0.048(4) Uiso 1 1 d . . .
H3 H 0.818(2) 0.4634(18) 0.4122(12) 0.046(4) Uiso 1 1 d . . .
H6 H 0.071(3) 0.4424(19) 0.2230(13) 0.050(4) Uiso 1 1 d . . .
H4 H 0.524(3) 0.688(2) 0.1947(13) 0.059(4) Uiso 1 1 d . . .
H1 H 0.450(3) 0.768(2) 0.4956(16) 0.075(5) Uiso 1 1 d . . .
H5 H 0.402(3) 0.591(2) 0.2800(15) 0.062(4) Uiso 1 1 d . . .
O1 O 0.74156(14) 0.64494(10) 0.62114(6) 0.0403(2) Uani 1 1 d . . .
O3 O 0.24638(14) 0.62992(10) 0.03506(6) 0.0406(2) Uani 1 1 d . . .
O2 O 0.56371(15) 0.70696(11) 0.45448(6) 0.0412(2) Uani 1 1 d . . .
C2 C 0.90483(19) 0.54191(14) 0.46132(8) 0.0326(3) Uani 1 1 d . . .
N2 N 0.06535(18) 0.48337(13) 0.15775(9) 0.0393(3) Uani 1 1 d . . .
C1 C 0.73069(18) 0.63642(12) 0.52122(8) 0.0301(2) Uani 1 1 d . . .
C3 C 0.24138(19) 0.57939(14) 0.13227(8) 0.0352(3) Uani 1 1 d . . .
N1 N 0.4098(2) 0.62316(17) 0.21237(9) 0.0576(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 0.0440(5) 0.0507(5) 0.0256(4) 0.0020(3) 0.0019(3) 0.0131(4)
O3 0.0439(4) 0.0503(5) 0.0259(4) 0.0073(3) -0.0040(3) -0.0160(4)
O2 0.0447(5) 0.0507(5) 0.0267(4) -0.0026(3) -0.0024(3) 0.0177(4)
C2 0.0354(5) 0.0355(5) 0.0266(5) 0.0005(4) 0.0022(4) 0.0045(4)
N2 0.0410(5) 0.0474(6) 0.0283(5) 0.0075(4) -0.0011(4) -0.0097(4)
C1 0.0322(5) 0.0307(5) 0.0270(5) 0.0015(4) 0.0010(4) 0.0004(4)
C3 0.0397(6) 0.0383(5) 0.0265(5) 0.0021(4) -0.0014(4) -0.0038(5)
N1 0.0614(7) 0.0805(9) 0.0276(6) 0.0124(5) -0.0097(5) -0.0342(6)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2176(12) . ?
O3 C3 1.2599(13) . ?
O2 C1 1.3108(13) . ?
C2 C1 1.5035(14) . ?
C2 C2 1.515(2) 3_766 ?
N2 C3 1.3306(15) . ?
C3 N1 1.3374(15) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C2 112.75(10) . 3_766 ?
O1 C1 O2 123.47(9) . . ?
O1 C1 C2 123.66(9) . . ?
O2 C1 C2 112.86(8) . . ?
O3 C3 N2 120.50(10) . . ?
O3 C3 N1 120.95(10) . . ?
N2 C3 N1 118.54(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
_geom_hbond_site_symmetry_A
O2 H1 O3 0.99(2) 1.54(2) 2.5211(11) 167.9(18) 4_576
N1 H4 O1 0.880(17) 2.102(18) 2.9658(14) 167.0(15) 4_575

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 992814'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_u_suc_300k

_audit_update_record             
;
2012-03-19 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 bis(urea) butanedioic acid
;
_chemical_name_common            
;
 bis(urea) succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H14 N4 O6'
_chemical_formula_weight         238.21

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.6366(6)
_cell_length_b                   8.2568(10)
_cell_length_c                   12.2790(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.659(4)
_cell_angle_gamma                90.00
_cell_volume                     567.61(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    4257
_cell_measurement_theta_min      6.68
_cell_measurement_theta_max      55.11

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9267
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
'Rigaku R-AXIS RAPID IP Image Plate diffractometer'
;
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7067
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1293
_reflns_number_gt                812
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.0409P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1293
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.979(3) 0.619(2) 0.4168(15) 0.064(5) Uiso 1 1 d . . .
H7 H -0.041(4) 0.454(2) 0.1023(18) 0.070(6) Uiso 1 1 d . . .
H3 H 0.814(3) 0.470(2) 0.4138(14) 0.054(4) Uiso 1 1 d . . .
H6 H 0.073(3) 0.451(2) 0.2204(16) 0.065(6) Uiso 1 1 d . . .
H4 H 0.529(4) 0.696(3) 0.1948(17) 0.087(7) Uiso 1 1 d . . .
H1 H 0.448(4) 0.768(3) 0.498(2) 0.104(7) Uiso 1 1 d . . .
H5 H 0.399(4) 0.601(3) 0.278(2) 0.084(6) Uiso 1 1 d . . .
O1 O 0.7399(2) 0.64117(14) 0.62058(8) 0.0588(4) Uani 1 1 d . . .
O3 O 0.2461(2) 0.63133(14) 0.03603(8) 0.0597(4) Uani 1 1 d . . .
O2 O 0.5668(2) 0.70910(15) 0.45536(9) 0.0600(4) Uani 1 1 d . . .
C2 C 0.9057(3) 0.5428(2) 0.46215(12) 0.0470(4) Uani 1 1 d . . .
N2 N 0.0657(3) 0.4863(2) 0.15702(13) 0.0583(4) Uani 1 1 d . . .
C1 C 0.7318(3) 0.63549(18) 0.52138(11) 0.0440(4) Uani 1 1 d . . .
C3 C 0.2416(3) 0.5821(2) 0.13254(11) 0.0497(4) Uani 1 1 d . . .
N1 N 0.4086(3) 0.6264(3) 0.21234(14) 0.0834(6) 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 0.0642(8) 0.0754(8) 0.0364(6) 0.0035(5) 0.0039(5) 0.0199(6)
O3 0.0648(8) 0.0745(8) 0.0373(6) 0.0106(5) -0.0050(5) -0.0244(6)
O2 0.0649(8) 0.0751(8) 0.0381(6) -0.0019(5) -0.0029(5) 0.0269(6)
C2 0.0499(9) 0.0514(9) 0.0391(8) -0.0002(7) 0.0030(7) 0.0056(7)
N2 0.0623(9) 0.0717(10) 0.0395(8) 0.0111(7) 0.0001(7) -0.0155(7)
C1 0.0466(8) 0.0459(8) 0.0384(8) 0.0022(6) 0.0007(6) 0.0016(7)
C3 0.0537(9) 0.0564(9) 0.0376(8) 0.0040(7) -0.0008(7) -0.0058(8)
N1 0.0868(13) 0.1190(16) 0.0395(9) 0.0163(9) -0.0134(8) -0.0471(11)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2145(16) . ?
O3 C3 1.2560(17) . ?
O2 C1 1.3103(18) . ?
C2 C1 1.497(2) . ?
C2 C2 1.505(3) 3_766 ?
N2 C3 1.330(2) . ?
C3 N1 1.329(2) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C2 113.30(15) . 3_766 ?
O1 C1 O2 122.97(14) . . ?
O1 C1 C2 123.81(13) . . ?
O2 C1 C2 113.22(12) . . ?
O3 C3 N1 121.07(15) . . ?
O3 C3 N2 120.22(15) . . ?
N1 C3 N2 118.70(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
_geom_hbond_site_symmetry_A
O2 H1 O3 1.02(3) 1.52(3) 2.5298(15) 167(2) 4_576
N1 H4 O1 0.93(2) 2.08(2) 2.988(2) 165.7(19) 4_575

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 992815'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ufa_30k_neutron

_audit_creation_date             2014-03-19T19:24:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C3 H6 N2 O3'
_chemical_formula_weight         118.09

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   5.7976(10)
_cell_length_b                   7.5666(10)
_cell_length_c                   12.351(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.03(3)
_cell_angle_gamma                90
_cell_volume                     537.72(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    30(2)
_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          5
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          1
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             135
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SXD2001 (Gutmann, 2001)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 For peak integration a local UB matrix refined for each frame, 
using approximately 100 reflections from each of the 11 detectors.
Hence _cell_measurement_reflns_used      1000

For final cell dimensions a weighted average of all local 
cells from each frame was calculated. 5 frames of data were collected  

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.7-6.9 Angstroms,
BUT the bulk of the diffraction information is obtained from 
wavelengths in the range 0.8-2.9 Angstroms.

The data collection procedures on the SXD instrument used
for the single crystal neutron data collection are most
recently summarised the following paper
D. A. Keen, M. J. Gutmann and C. C. Wilson, J. Appl. Cryst., 2006, 39, 714. ?
;
_diffrn_ambient_temperature      30(2)
_diffrn_radiation_wavelength     0.7-6.9
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ISIS spallation source'
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  SXD
_diffrn_measurement_method       'time-of-flight LAUE diffraction'

_diffrn_reflns_number            5451
_diffrn_reflns_theta_min         8.787
_diffrn_reflns_theta_max         81.536
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.209
_diffrn_measured_fraction_theta_full 0.815
_diffrn_reflns_Laue_measured_fraction_full 0.815
_diffrn_reflns_Laue_measured_fraction_max 0.209
_diffrn_reflns_point_group_measured_fraction_full 0.815
_diffrn_reflns_point_group_measured_fraction_max 0.209
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   difmap

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 ?
;
_reflns_number_total             5451
_reflns_number_gt                5451
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1268
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_refine_ls_number_reflns         5451
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0582P)²+8.7832P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.725
_refine_diff_density_min         -1.499
_refine_diff_density_rms         0.382
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0104(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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.5579(3) 0.19488(16) 0.95985(8) 0.0063(2) Uani d 1 . . O
O2 0.7629(3) 0.16814(17) 1.12541(8) 0.0071(2) Uani d 1 . . O
C1 0.7347(2) 0.13823(13) 1.02667(6) 0.00431(19) Uani d 1 . . C
C2 0.9019(3) 0.03023(13) 0.97222(7) 0.0059(2) Uani d 1 . . C
O3 0.2657(3) 0.38912(16) 1.03379(8) 0.0071(2) Uani d 1 . . O
N1 0.4219(2) 0.39831(11) 1.21209(5) 0.01012(19) Uani d 1 . . N
N2 1.07731(19) -0.04227(10) 0.65357(5) 0.00779(17) Uani d 1 . . N
C3 0.2557(2) 0.44170(13) 1.13067(6) 0.0051(2) Uani d 1 . . C
H1 0.4442(6) 0.2779(4) 0.99965(19) 0.0178(5) Uani d 1 . . H
H6 0.9498(7) -0.0691(4) 0.5916(2) 0.0209(6) Uani d 1 . . H
H2 0.8587(8) 0.0023(5) 0.88564(19) 0.0255(7) Uani d 1 . . H
H5 0.9234(7) 0.0921(4) 1.2705(2) 0.0221(6) Uani d 1 . . H
H4 0.4069(8) 0.0687(5) 0.79010(19) 0.0266(8) Uani d 1 . . H
H3 0.5538(7) 0.3199(4) 1.1938(2) 0.0241(7) Uani d 1 . . H

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0068(7) 0.0078(4) 0.0042(3) 0.0022(4) 0.0000(3) -0.0006(2)
O2 0.0075(7) 0.0100(4) 0.0036(3) 0.0030(4) 0.0006(3) -0.0004(2)
C1 0.0045(6) 0.0048(3) 0.0036(2) 0.0005(3) 0.0003(3) 0.00017(19)
C2 0.0058(6) 0.0071(4) 0.0045(2) 0.0016(3) 0.0000(3) -0.0002(2)
O3 0.0085(7) 0.0087(4) 0.0040(3) 0.0027(4) 0.0000(3) -0.0017(2)
N1 0.0112(5) 0.0139(3) 0.00467(18) 0.0058(3) -0.0015(3) -0.00162(18)
N2 0.0065(5) 0.0104(3) 0.0063(2) -0.0023(3) -0.0001(2) 0.00229(17)
C3 0.0059(6) 0.0056(3) 0.0037(2) 0.0010(3) 0.0001(3) -0.0009(2)
H1 0.0177(15) 0.0196(10) 0.0156(7) 0.0027(10) -0.0001(8) -0.0002(7)
H6 0.0166(17) 0.0283(13) 0.0166(8) -0.0076(12) -0.0029(10) 0.0017(8)
H2 0.0244(19) 0.0398(16) 0.0114(7) 0.0100(14) -0.0021(10) -0.0064(8)
H5 0.0238(18) 0.0282(13) 0.0141(7) -0.0077(12) 0.0018(10) 0.0074(7)
H4 0.029(2) 0.0397(16) 0.0109(7) -0.0084(15) 0.0005(10) 0.0063(8)
H3 0.021(2) 0.0299(14) 0.0207(9) 0.0126(13) -0.0005(11) -0.0031(9)


#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.3073(17) ?
O2 C1 . 1.2313(13) ?
C1 C2 . 1.4896(18) ?
C2 C2 3_757 1.335(2) ?
O3 C3 . 1.2691(14) ?
N1 C3 . 1.3453(13) ?
N2 C3 4_665 1.3418(16) ?
C3 N2 4_466 1.3418(16) ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 124.29(14) . . ?
O2 C1 C2 122.24(12) . . ?
O1 C1 C2 113.47(9) . . ?
C2 C2 C1 121.08(10) 3_757 . ?
O3 C3 N2 120.13(11) . 4_466 ?
O3 C3 N1 121.13(13) . . ?
N2 C3 N1 118.74(8) 4_466 . ?

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
O1 H1 O3 1.072(4) 1.437(4) 2.498(2) 169.4(2) .
N1 H3 O2 1.015(4) 1.937(4) 2.9337(19) 166.5(2) .
N2 H6 O3 1.018(3) 1.893(3) 2.9072(17) 174.1(3) 2_646

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 992816'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ufa100sb

# start Validation Reply Form
_vrf_TYPE031_ufa100sb            
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
# end Validation Reply Form

_audit_update_record             
;
2010-11-23 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'bis(Urea) fumaric acid'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H6 N2 O3'
_chemical_formula_weight         118.09

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.766(2)
_cell_length_b                   7.666(3)
_cell_length_c                   12.332(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.81(3)
_cell_angle_gamma                90.00
_cell_volume                     541.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    330
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          6
_exptl_crystal_size_mid          2
_exptl_crystal_size_min          2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             135
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
For peak integration a local UB matrix refined for each frame, 
using approximately 30 reflections from each of the 11 detectors.
Hence _cell_measurement_reflns_used      330

For final cell dimensions a weighted average of all local 
cells was calculated  

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.7-6.9 Angstroms,
BUT the bulk of the diffraction information is obtained from 
wavelengths in the range 0.8-2.9 Angstroms.

The data collection procedures on the SXD instrument used
for the single crystal neutron data collection are most
recently summarised in the Appendix to the following paper
     Wilson, C.C. (1997).  J. Mol. Struct. 405, 207-217. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7-6.9
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ISIS spallation source'
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  SXD
_diffrn_measurement_method       'time-of-flight LAUE diffraction'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3581
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0898
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         10.00
_diffrn_reflns_theta_max         82.53
_reflns_number_total             3581
_reflns_number_gt                3581
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SXD-2001
_computing_cell_refinement       SXD-2001
_computing_data_reduction        SXD-2001
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 The variable wavelength nature of the data collection
procedure means that sensible values of 
_diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min      0.09
_diffrn_reflns_sin(theta)/lambda_max      1.11

_refine_diff_density_max/min is given in Fermi per per angstrom cubed not
electons per angstrom cubed. Another way to consider the _refine_diff_density_ 
is as a percentage of the diffracted intensity of a given atom:
_refine_diff_density_max =  2.7% of Carbon
_refine_diff_density_min = -2.7% of Carbon

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0672P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0075(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3581
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5583(2) 0.19564(13) -0.03966(15) 0.0122(4) Uani 1 1 d . . .
O2 O 0.7610(2) 0.16568(15) 0.12561(17) 0.0151(4) Uani 1 1 d . . .
C1 C 0.73428(17) 0.13790(11) 0.02698(13) 0.0094(3) Uani 1 1 d . . .
C2 C 0.90262(17) 0.03163(12) -0.02774(15) 0.0115(3) Uani 1 1 d . . .
O3 O 0.2637(2) 0.38639(14) 0.03426(16) 0.0151(4) Uani 1 1 d . . .
N1 N 0.41959(16) 0.39507(11) 0.21213(13) 0.0224(3) Uani 1 1 d . . .
N2 N 0.07538(14) 0.53943(10) 0.15388(11) 0.0156(3) Uani 1 1 d . . .
C3 C 0.25317(16) 0.43889(12) 0.13088(13) 0.0118(3) Uani 1 1 d . . .
H1 H 0.4437(4) 0.2767(3) 0.0000(3) 0.0235(7) Uani 1 1 d . . .
H6 H -0.0502(4) 0.5679(3) 0.0925(3) 0.0270(8) Uani 1 1 d . . .
H2 H 0.8609(5) 0.0068(4) -0.1143(4) 0.0381(10) Uani 1 1 d . . .
H5 H 0.0755(4) 0.5896(3) 0.2295(3) 0.0272(8) Uani 1 1 d . . .
H4 H 0.4069(5) 0.4284(4) 0.2909(4) 0.0358(10) Uani 1 1 d . . .
H3 H 0.5507(4) 0.3164(3) 0.1942(3) 0.0339(9) 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 0.0144(5) 0.0174(4) 0.0037(13) -0.0019(5) -0.0029(5) 0.0055(3)
O2 0.0159(5) 0.0222(5) 0.0066(14) -0.0018(6) -0.0015(5) 0.0054(3)
C1 0.0114(4) 0.0131(3) 0.0032(11) 0.0007(4) -0.0009(4) 0.0015(3)
C2 0.0123(4) 0.0155(4) 0.0063(11) -0.0006(4) -0.0003(4) 0.0030(3)
O3 0.0171(6) 0.0202(5) 0.0072(14) -0.0045(5) -0.0021(6) 0.0065(3)
N1 0.0261(5) 0.0336(4) 0.0055(12) -0.0049(4) -0.0057(5) 0.0146(3)
N2 0.0143(4) 0.0231(3) 0.0087(10) -0.0064(4) -0.0013(4) 0.0042(2)
C3 0.0134(4) 0.0154(4) 0.0060(11) -0.0032(4) -0.0017(4) 0.0030(3)
H1 0.0260(11) 0.0282(9) 0.015(3) -0.0007(11) -0.0021(10) 0.0054(7)
H6 0.0263(12) 0.0391(11) 0.014(3) -0.0069(12) -0.0051(12) 0.0079(9)
H2 0.0397(16) 0.0616(17) 0.011(3) -0.0115(16) -0.0070(14) 0.0213(11)
H5 0.0324(12) 0.0377(11) 0.011(3) -0.0092(13) -0.0004(12) 0.0048(8)
H4 0.0411(15) 0.0604(16) 0.004(4) -0.0074(17) -0.0041(14) 0.0107(12)
H3 0.0349(14) 0.0434(12) 0.021(3) -0.0070(13) -0.0050(13) 0.0197(10)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.305(2) . ?
O1 H1 1.067(3) . ?
O2 C1 1.226(2) . ?
C1 C2 1.4888(15) . ?
C2 C2 1.335(3) 3_755 ?
C2 H2 1.083(6) . ?
O3 C3 1.266(2) . ?
O3 H1 1.438(2) . ?
N1 C3 1.345(2) . ?
N1 H4 1.015(5) . ?
N1 H3 1.012(2) . ?
N2 C3 1.3396(12) . ?
N2 H6 1.008(4) . ?
N2 H5 1.009(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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 112.7(2) . . ?
O2 C1 O1 124.22(11) . . ?
O2 C1 C2 122.19(12) . . ?
O1 C1 C2 113.60(14) . . ?
C2 C2 C1 121.4(2) 3_755 . ?
C2 C2 H2 121.1(2) 3_755 . ?
C1 C2 H2 117.53(17) . . ?
C3 O3 H1 125.4(2) . . ?
C3 N1 H4 121.6(2) . . ?
C3 N1 H3 118.2(3) . . ?
H4 N1 H3 120.0(3) . . ?
C3 N2 H6 117.72(19) . . ?
C3 N2 H5 119.90(19) . . ?
H6 N2 H5 122.3(2) . . ?
O3 C3 N2 120.37(14) . . ?
O3 C3 N1 120.81(10) . . ?
N2 C3 N1 118.82(14) . . ?

_diffrn_measured_fraction_theta_max 0.003
_diffrn_reflns_theta_full        82.53
_diffrn_measured_fraction_theta_full 0.003
_refine_diff_density_max         0.906
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.216
_database_code_depnum_ccdc_archive 'CCDC 992817'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ufa200sb

# start Validation Reply Form
_vrf_TYPE031_ufa200sb            
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
# end Validation Reply Form

_audit_update_record             
;
2010-11-23 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'bis(Urea) fumaric acid'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H6 N2 O3'
_chemical_formula_weight         118.09

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.676(2)
_cell_length_b                   7.912(3)
_cell_length_c                   12.366(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.66(3)
_cell_angle_gamma                90.00
_cell_volume                     551.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    330
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          6
_exptl_crystal_size_mid          2
_exptl_crystal_size_min          2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             135
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 For peak integration a local UB matrix refined for each frame, 
using approximately 30 reflections from each of the 11 detectors.
Hence _cell_measurement_reflns_used      330

For final cell dimensions a weighted average of all local 
cells was calculated  

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.7-6.9 Angstroms,
BUT the bulk of the diffraction information is obtained from 
wavelengths in the range 0.8-3.0 Angstroms.

The data collection procedures on the SXD instrument used
for the single crystal neutron data collection are most
recently summarised in the Appendix to the following paper
     Wilson, C.C. (1997).  J. Mol. Struct. 405, 207-217. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.7-6.9
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ISIS spallation source'
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  SXD
_diffrn_measurement_method       'time-of-flight LAUE diffraction'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3023
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         9.33
_diffrn_reflns_theta_max         83.02
_reflns_number_total             3023
_reflns_number_gt                3023
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SXD-2001
_computing_cell_refinement       SXD-2001
_computing_data_reduction        SXD-2001
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 The variable wavelength nature of the data collection
procedure means that sensible values of 
_diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min      0.09
_diffrn_reflns_sin(theta)/lambda_max      0.87

_refine_diff_density_max/min is given in Fermi per per angstrom cubed not
electons per angstrom cubed. Another way to consider the _refine_diff_density_ 
is as a percentage of the diffracted intensity of a given atom:
_refine_diff_density_max =  3.1% of Carbon
_refine_diff_density_min = -3.7% of Carbon

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0778P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0134(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3023
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5619(3) 0.19879(18) -0.03852(17) 0.0295(5) Uani 1 1 d . . .
O2 O 0.7561(3) 0.15793(19) 0.12687(19) 0.0318(5) Uani 1 1 d . . .
C1 C 0.7349(2) 0.13714(13) 0.02778(14) 0.0217(4) Uani 1 1 d . . .
C2 C 0.9057(3) 0.03560(15) -0.02734(16) 0.0254(4) Uani 1 1 d . . .
O3 O 0.2581(3) 0.37993(19) 0.03591(18) 0.0321(5) Uani 1 1 d . . .
N1 N 0.4130(3) 0.38686(16) 0.21300(14) 0.0477(4) Uani 1 1 d . . .
N2 N 0.0708(2) 0.53229(13) 0.15450(14) 0.0333(4) Uani 1 1 d . . .
C3 C 0.2480(3) 0.43159(15) 0.13134(16) 0.0268(4) Uani 1 1 d . . .
H1 H 0.4437(6) 0.2759(3) 0.0008(3) 0.0402(9) Uani 1 1 d . . .
H6 H -0.0504(7) 0.5656(4) 0.0918(4) 0.0435(10) Uani 1 1 d . . .
H2 H 0.8676(8) 0.0185(6) -0.1144(4) 0.0713(14) Uani 1 1 d . . .
H5 H 0.0739(6) 0.5829(4) 0.2283(4) 0.0428(9) Uani 1 1 d . . .
H4 H 0.4029(8) 0.4223(5) 0.2908(4) 0.0584(11) Uani 1 1 d . . .
H3 H 0.5456(6) 0.3092(4) 0.1954(4) 0.0567(11) 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 0.0323(10) 0.0391(7) 0.0159(13) -0.0027(7) -0.0028(9) 0.0150(7)
O2 0.0342(10) 0.0452(8) 0.0152(14) 0.0010(8) 0.0000(10) 0.0127(6)
C1 0.0236(7) 0.0282(5) 0.0125(11) 0.0017(5) -0.0017(7) 0.0044(5)
C2 0.0251(8) 0.0328(6) 0.0179(12) 0.0000(6) 0.0003(8) 0.0077(5)
O3 0.0334(10) 0.0444(8) 0.0160(14) -0.0085(8) -0.0076(10) 0.0157(7)
N1 0.0512(9) 0.0707(8) 0.0181(12) -0.0102(7) -0.0089(9) 0.0305(6)
N2 0.0281(7) 0.0467(6) 0.0235(11) -0.0123(6) -0.0029(7) 0.0092(5)
C3 0.0288(8) 0.0339(6) 0.0165(12) -0.0051(6) -0.0032(8) 0.0069(5)
H1 0.0433(19) 0.0454(13) 0.031(3) -0.0030(13) -0.0006(18) 0.0103(12)
H6 0.0380(19) 0.0564(16) 0.034(3) -0.0095(16) -0.005(2) 0.0121(14)
H2 0.070(3) 0.117(3) 0.024(3) -0.011(2) -0.005(2) 0.050(2)
H5 0.0437(19) 0.0580(15) 0.026(3) -0.0118(15) -0.0007(19) 0.0063(13)
H4 0.059(3) 0.095(2) 0.018(3) -0.0158(19) -0.009(2) 0.0172(19)
H3 0.053(2) 0.0736(19) 0.040(3) -0.0097(18) -0.010(2) 0.0310(17)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.299(3) . ?
O1 H1 1.065(3) . ?
O2 C1 1.228(3) . ?
C1 C2 1.4845(18) . ?
C2 C2 1.324(3) 3_755 ?
C2 H2 1.081(6) . ?
O3 C3 1.256(3) . ?
O3 H1 1.443(3) . ?
N1 C3 1.343(3) . ?
N1 H4 1.009(5) . ?
N1 H3 1.015(3) . ?
N2 C3 1.3396(16) . ?
N2 H6 1.010(6) . ?
N2 H5 0.995(5) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 113.4(3) . . ?
O2 C1 O1 123.98(14) . . ?
O2 C1 C2 122.46(16) . . ?
O1 C1 C2 113.55(16) . . ?
C2 C2 C1 121.9(2) 3_755 . ?
C2 C2 H2 120.8(2) 3_755 . ?
C1 C2 H2 117.3(2) . . ?
C3 O3 H1 125.6(2) . . ?
C3 N1 H4 122.1(3) . . ?
C3 N1 H3 117.9(3) . . ?
H4 N1 H3 119.8(4) . . ?
C3 N2 H6 116.9(2) . . ?
C3 N2 H5 120.1(3) . . ?
H6 N2 H5 122.5(3) . . ?
O3 C3 N2 120.76(18) . . ?
O3 C3 N1 121.12(13) . . ?
N2 C3 N1 118.12(16) . . ?

_diffrn_measured_fraction_theta_max 0.002
_diffrn_reflns_theta_full        83.02
_diffrn_measured_fraction_theta_full 0.002
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.164
_database_code_depnum_ccdc_archive 'CCDC 992818'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ufa300sb

# start Validation Reply Form
_vrf_TYPE031_ufa300sb            
;
PROBLEM: _diffrn_radiation_wavelength is not of type numb.
RESPONSE: These are Laue neutron data therefore a wavelength range is given.
;
# end Validation Reply Form

_audit_update_record             
;
2010-11-23 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'bis(Urea) fumaric acid'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H6 N2 O3'
_chemical_formula_weight         118.09

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.549(2)
_cell_length_b                   8.239(3)
_cell_length_c                   12.445(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.24(3)
_cell_angle_gamma                90.00
_cell_volume                     564.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    330
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          6
_exptl_crystal_size_mid          2
_exptl_crystal_size_min          2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             135
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 For peak integration a local UB matrix refined for each frame, 
using approximately 30 reflections from each of the 11 detectors.
Hence _cell_measurement_reflns_used      330

For final cell dimensions a weighted average of all local 
cells was calculated  

Because of the nature of the experiment, it is not possible to give values of
theta_min and theta_max for the cell determination.

The same applies for the wavelength used for the experiment.
The range of wavelengths used was 0.7-6.6 Angstroms,
BUT the bulk of the diffraction information is obtained from 
wavelengths in the range 0.8-4.0 Angstroms.

The data collection procedures on the SXD instrument used
for the single crystal neutron data collection are most
recently summarised in the Appendix to the following paper
     Wilson, C.C. (1997).  J. Mol. Struct. 405, 207-217. 
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.7-6.6
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'ISIS spallation source'
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  SXD
_diffrn_measurement_method       'time-of-flight LAUE diffraction'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2053
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         8.98
_diffrn_reflns_theta_max         81.52
_reflns_number_total             2053
_reflns_number_gt                2053
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SXD-2001
_computing_cell_refinement       SXD-2001
_computing_data_reduction        SXD-2001
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 The variable wavelength nature of the data collection
procedure means that sensible values of 
_diffrn_reflns_theta_min & _diffrn_reflns_theta_max
cannot be given instead the following limits are given

_diffrn_reflns_sin(theta)/lambda_min      0.09
_diffrn_reflns_sin(theta)/lambda_max      0.86

_refine_diff_density_max/min is given in Fermi per per angstrom cubed not
electons per angstrom cubed. Another way to consider the _refine_diff_density_ 
is as a percentage of the diffracted intensity of a given atom:
_refine_diff_density_max =  3.9% of Carbon
_refine_diff_density_min = -3.5% of Carbon

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0884P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0201(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2053
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5677(5) 0.2046(3) -0.0369(2) 0.0541(8) Uani 1 1 d . . .
O2 O 0.7485(5) 0.1449(3) 0.1271(3) 0.0540(8) Uani 1 1 d . . .
C1 C 0.7352(4) 0.1361(2) 0.0287(2) 0.0375(6) Uani 1 1 d . . .
C2 C 0.9100(4) 0.0414(2) -0.0273(3) 0.0445(7) Uani 1 1 d . . .
O3 O 0.2521(5) 0.3720(3) 0.0382(3) 0.0542(8) Uani 1 1 d . . .
N1 N 0.4077(4) 0.3743(3) 0.2146(2) 0.0750(8) Uani 1 1 d . . .
N2 N 0.0664(4) 0.5219(2) 0.1549(2) 0.0547(7) Uani 1 1 d . . .
C3 C 0.2428(4) 0.4215(2) 0.1323(2) 0.0448(7) Uani 1 1 d . . .
H1 H 0.4460(9) 0.2759(5) 0.0029(4) 0.0627(14) Uani 1 1 d . . .
H6 H -0.0488(11) 0.5604(6) 0.0913(7) 0.0634(15) Uani 1 1 d . . .
H2 H 0.8864(13) 0.0413(9) -0.1120(7) 0.113(3) Uani 1 1 d . . .
H5 H 0.0718(10) 0.5709(6) 0.2275(5) 0.0633(15) Uani 1 1 d . . .
H4 H 0.4003(11) 0.4094(8) 0.2904(6) 0.0842(18) Uani 1 1 d . . .
H3 H 0.5403(11) 0.2987(7) 0.1970(5) 0.0848(17) 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 0.0573(18) 0.0743(15) 0.029(2) -0.0040(14) -0.0031(17) 0.0299(14)
O2 0.062(2) 0.0751(15) 0.025(2) 0.0040(13) 0.0066(17) 0.0227(12)
C1 0.0415(13) 0.0480(9) 0.0222(18) 0.0030(9) 0.0010(12) 0.0093(9)
C2 0.0437(14) 0.0536(11) 0.035(2) 0.0014(10) 0.0015(14) 0.0148(8)
O3 0.0588(18) 0.0731(15) 0.027(2) -0.0132(13) -0.0083(15) 0.0286(13)
N1 0.0780(17) 0.1092(14) 0.034(2) -0.0123(14) -0.0100(16) 0.0421(12)
N2 0.0513(13) 0.0740(12) 0.0370(19) -0.0158(10) -0.0020(13) 0.0158(9)
C3 0.0458(15) 0.0573(10) 0.028(2) -0.0080(10) -0.0067(14) 0.0129(9)
H1 0.068(3) 0.075(2) 0.044(4) -0.003(2) 0.001(3) 0.022(2)
H6 0.061(3) 0.077(3) 0.050(5) -0.008(3) -0.003(3) 0.021(2)
H2 0.113(5) 0.180(6) 0.044(6) 0.002(4) 0.004(5) 0.088(5)
H5 0.069(3) 0.085(3) 0.036(4) -0.015(2) 0.003(3) 0.008(2)
H4 0.077(4) 0.137(4) 0.034(6) -0.019(3) -0.010(4) 0.025(3)
H3 0.087(4) 0.118(3) 0.044(4) -0.017(3) -0.014(3) 0.041(3)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.288(4) . ?
O1 H1 1.063(5) . ?
O2 C1 1.220(4) . ?
C1 C2 1.486(3) . ?
C2 C2 1.325(5) 3_755 ?
C2 H2 1.045(10) . ?
O3 C3 1.246(4) . ?
O3 H1 1.448(5) . ?
N1 C3 1.343(4) . ?
N1 H4 0.992(9) . ?
N1 H3 1.009(7) . ?
N2 C3 1.338(3) . ?
N2 H6 1.005(10) . ?
N2 H5 0.986(7) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 113.4(4) . . ?
O2 C1 O1 123.91(19) . . ?
O2 C1 C2 122.9(2) . . ?
O1 C1 C2 113.2(2) . . ?
C2 C2 C1 121.6(4) 3_755 . ?
C2 C2 H2 120.5(4) 3_755 . ?
C1 C2 H2 117.9(3) . . ?
C3 O3 H1 125.8(3) . . ?
C3 N1 H4 122.4(4) . . ?
C3 N1 H3 117.3(5) . . ?
H4 N1 H3 120.3(6) . . ?
C3 N2 H6 116.0(3) . . ?
C3 N2 H5 120.5(4) . . ?
H6 N2 H5 122.4(4) . . ?
O3 C3 N2 121.2(3) . . ?
O3 C3 N1 121.1(2) . . ?
N2 C3 N1 117.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.001
_diffrn_reflns_theta_full        81.52
_diffrn_measured_fraction_theta_full 0.001
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.099
_database_code_depnum_ccdc_archive 'CCDC 992819'

